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1501957.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501957
loop_
_publ_author_name
'Kawatsura, Motoi'
'Yamamoto, Mitsuaki'
'Namioka, Junya'
'Kajita, Koji'
'Hirakawa, Takuya'
'Itoh, Toshiyuki'
_publ_section_title
;
Ruthenium-catalyzed regioselective [2 + 2 + 2] cyclotrimerization of
trifluoromethyl group substituted internal alkynes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1001
_journal_page_last 1003
_journal_paper_doi 10.1021/ol1030734
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C42 H28 F6 N O3 P Ru '
_chemical_formula_sum 'C42 H28 F6 N O3 P Ru'
_chemical_formula_weight 840.72
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_cell_angle_alpha 90.0000
_cell_angle_beta 97.869(17)
_cell_angle_gamma 90.0000
_cell_formula_units_Z 4
_cell_length_a 11.192(5)
_cell_length_b 18.427(5)
_cell_length_c 18.549(6)
_cell_measurement_reflns_used 14220
_cell_measurement_temperature 173.1
_cell_measurement_theta_max 27.2
_cell_measurement_theta_min 3.0
_cell_volume 3789(2)
_computing_cell_refinement PROCESS-AUTO
_computing_data_collection PROCESS-AUTO
_computing_data_reduction CrystalStructure
_computing_publication_material 'CrystalStructure 3.8'
_computing_structure_refinement CRYSTALS
_computing_structure_solution SIR2004
_diffrn_ambient_temperature 173
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method \w
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71075
_diffrn_reflns_av_R_equivalents 0.103
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 31542
_diffrn_reflns_theta_full 27.40
_diffrn_reflns_theta_max 27.40
_exptl_absorpt_coefficient_mu 0.525
_exptl_absorpt_correction_T_max 0.949
_exptl_absorpt_correction_T_min 0.415
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.473
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 1696.00
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.56
_refine_diff_density_min -0.95
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.000
_refine_ls_hydrogen_treatment refall
_refine_ls_number_parameters 515
_refine_ls_number_reflns 4713
_refine_ls_R_factor_gt 0.0474
_refine_ls_shift/su_max 0.0030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0012Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.1150
_reflns_number_gt 4666
_reflns_number_total 8336
_reflns_threshold_expression F^2^>2.0\s(F^2^)
_cod_data_source_file ol1030734_si_001.cif
_cod_data_source_block '_My-2_____________________'
_cod_original_cell_volume 3790(2)
_cod_original_formula_sum 'C42 H28 F6 N O3 P Ru '
_cod_database_code 1501957
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ru(1) Ru 0.01745(4) 0.14167(2) 0.94191(2) 0.02135(10) Uani 1.00 1 d .
P(1) P 0.17925(13) 0.20416(8) 0.88821(8) 0.0214(3) Uani 1.00 1 d .
F(1) F 0.1524(3) 0.2442(2) 1.07888(19) 0.0439(10) Uani 1.00 1 d .
F(2) F 0.0248(3) 0.3298(2) 1.09102(18) 0.0425(10) Uani 1.00 1 d .
F(3) F -0.0140(3) 0.2184(2) 1.12214(18) 0.0493(12) Uani 1.00 1 d .
F(4) F -0.1506(3) 0.0847(2) 0.7927(2) 0.0634(13) Uani 1.00 1 d .
F(5) F -0.2842(3) 0.1688(2) 0.7716(2) 0.0552(12) Uani 1.00 1 d .
F(6) F -0.1089(4) 0.1834(2) 0.7386(2) 0.0670(14) Uani 1.00 1 d .
O(1) O 0.1863(4) 0.0800(2) 1.0726(2) 0.0423(13) Uani 1.00 1 d .
O(2) O -0.2191(4) 0.0927(2) 0.9969(3) 0.0596(17) Uani 1.00 1 d .
O(4) O 0.0502(4) -0.0088(2) 0.8672(2) 0.0390(13) Uani 1.00 1 d .
N(1) N 0.3442(5) 0.0178(2) 0.9180(3) 0.0438(17) Uani 1.00 1 d .
C(1) C -0.0275(4) 0.2400(3) 0.9950(2) 0.0235(14) Uani 1.00 1 d .
C(2) C -0.1206(4) 0.2819(2) 0.9612(2) 0.0225(14) Uani 1.00 1 d .
C(3) C -0.1653(4) 0.2562(2) 0.8861(2) 0.0223(14) Uani 1.00 1 d .
C(4) C -0.1167(4) 0.1930(3) 0.8644(3) 0.0261(15) Uani 1.00 1 d .
C(5) C 0.0310(5) 0.2586(3) 1.0701(3) 0.0307(16) Uani 1.00 1 d .
C(6) C -0.1823(4) 0.3456(2) 0.9948(3) 0.0244(14) Uani 1.00 1 d .
C(7) C -0.2329(5) 0.3352(3) 1.0586(3) 0.0308(16) Uani 1.00 1 d .
C(8) C -0.2966(5) 0.3916(3) 1.0885(2) 0.0286(15) Uani 1.00 1 d .
C(9) C -0.3146(5) 0.4596(3) 1.0530(3) 0.0289(16) Uani 1.00 1 d .
C(10) C -0.2630(5) 0.4703(3) 0.9892(3) 0.0314(16) Uani 1.00 1 d .
C(11) C -0.1976(5) 0.4136(3) 0.9585(2) 0.0269(15) Uani 1.00 1 d .
C(12) C -0.3874(5) 0.5198(3) 1.0835(3) 0.0421(19) Uani 1.00 1 d .
C(13) C -0.2613(4) 0.3010(3) 0.8423(3) 0.0248(14) Uani 1.00 1 d .
C(14) C -0.3797(5) 0.3045(3) 0.8598(2) 0.0265(15) Uani 1.00 1 d .
C(15) C -0.4678(5) 0.3459(3) 0.8162(3) 0.0313(16) Uani 1.00 1 d .
C(16) C -0.4410(5) 0.3861(3) 0.7584(3) 0.0347(17) Uani 1.00 1 d .
C(17) C -0.3218(5) 0.3835(3) 0.7392(3) 0.0351(17) Uani 1.00 1 d .
C(18) C -0.2335(5) 0.3407(3) 0.7818(2) 0.0282(15) Uani 1.00 1 d .
C(19) C -0.5376(6) 0.4318(4) 0.7127(3) 0.047(2) Uani 1.00 1 d .
C(20) C -0.1659(5) 0.1586(3) 0.7941(3) 0.0367(18) Uani 1.00 1 d .
C(21) C 0.1275(5) 0.1045(3) 1.0251(3) 0.0325(17) Uani 1.00 1 d .
C(22) C -0.1288(6) 0.1081(3) 0.9791(3) 0.0324(17) Uani 1.00 1 d .
C(23) C 0.0396(5) 0.0487(3) 0.8918(3) 0.0269(15) Uani 1.00 1 d .
C(24) C 0.3189(4) 0.2108(3) 0.9533(2) 0.0227(14) Uani 1.00 1 d .
C(25) C 0.3876(4) 0.1474(3) 0.9754(2) 0.0263(14) Uani 1.00 1 d .
C(26) C 0.4870(5) 0.1507(3) 1.0306(3) 0.0383(17) Uani 1.00 1 d .
C(27) C 0.5181(5) 0.2163(3) 1.0627(3) 0.045(2) Uani 1.00 1 d .
C(28) C 0.4541(5) 0.2805(3) 1.0418(3) 0.043(2) Uani 1.00 1 d .
C(29) C 0.3562(5) 0.2762(3) 0.9882(3) 0.0352(17) Uani 1.00 1 d .
C(30) C 0.3611(5) 0.0757(3) 0.9421(3) 0.0358(18) Uani 1.00 1 d .
C(31) C 0.1455(4) 0.2986(3) 0.8568(2) 0.0243(14) Uani 1.00 1 d .
C(32) C 0.1132(4) 0.3542(3) 0.9028(3) 0.0296(14) Uani 1.00 1 d .
C(33) C 0.0832(5) 0.4245(3) 0.8762(3) 0.0283(15) Uani 1.00 1 d .
C(34) C 0.0856(5) 0.4411(3) 0.8032(3) 0.0353(17) Uani 1.00 1 d .
C(35) C 0.1170(5) 0.3876(3) 0.7588(4) 0.0433(19) Uani 1.00 1 d .
C(36) C 0.1467(5) 0.3164(3) 0.7832(2) 0.0315(16) Uani 1.00 1 d .
C(37) C 0.2385(5) 0.1600(3) 0.8109(2) 0.0269(15) Uani 1.00 1 d .
C(38) C 0.1664(5) 0.1137(3) 0.7614(2) 0.0299(15) Uani 1.00 1 d .
C(39) C 0.2151(6) 0.0785(3) 0.7050(3) 0.047(2) Uani 1.00 1 d .
C(40) C 0.3341(6) 0.0922(4) 0.6938(3) 0.049(2) Uani 1.00 1 d .
C(41) C 0.4055(5) 0.1394(4) 0.7410(3) 0.0454(19) Uani 1.00 1 d .
C(42) C 0.3578(5) 0.1736(3) 0.7985(3) 0.0379(18) Uani 1.00 1 d .
H(1) H -0.2241 0.2897 1.0828 0.037 Uiso 1.00 1 c R
H(2) H -0.3279 0.3839 1.1330 0.035 Uiso 1.00 1 c R
H(3) H -0.2709 0.5160 0.9654 0.037 Uiso 1.00 1 c R
H(4) H -0.1645 0.4215 0.9146 0.033 Uiso 1.00 1 c R
H(5) H -0.4000 0.2784 0.9006 0.032 Uiso 1.00 1 c R
H(6) H -0.5478 0.3465 0.8279 0.038 Uiso 1.00 1 c R
H(7) H -0.3017 0.4105 0.6988 0.042 Uiso 1.00 1 c R
H(8) H -0.1540 0.3387 0.7693 0.034 Uiso 1.00 1 c R
H(9) H 0.5330 0.1084 1.0445 0.045 Uiso 1.00 1 c R
H(10) H 0.5838 0.2184 1.1009 0.053 Uiso 1.00 1 c R
H(11) H 0.4774 0.3254 1.0645 0.051 Uiso 1.00 1 c R
H(12) H 0.3128 0.3193 0.9737 0.042 Uiso 1.00 1 c R
H(13) H 0.1114 0.3434 0.9527 0.035 Uiso 1.00 1 c R
H(14) H 0.0616 0.4607 0.9085 0.034 Uiso 1.00 1 c R
H(15) H 0.0664 0.4885 0.7852 0.043 Uiso 1.00 1 c R
H(16) H 0.1180 0.3985 0.7088 0.052 Uiso 1.00 1 c R
H(17) H 0.1676 0.2805 0.7504 0.038 Uiso 1.00 1 c R
H(18) H 0.0845 0.1060 0.7677 0.036 Uiso 1.00 1 c R
H(19) H 0.1668 0.0457 0.6740 0.055 Uiso 1.00 1 c R
H(20) H 0.3664 0.0687 0.6552 0.060 Uiso 1.00 1 c R
H(21) H 0.4863 0.1486 0.7334 0.055 Uiso 1.00 1 c R
H(22) H 0.4063 0.2063 0.8294 0.046 Uiso 1.00 1 c R
H(23) H -0.4698 0.5153 1.0634 0.051 Uiso 1.00 1 c R
H(24) H -0.3579 0.5658 1.0710 0.051 Uiso 1.00 1 c R
H(25) H -0.3799 0.5155 1.1349 0.051 Uiso 1.00 1 c R
H(26) H -0.5776 0.4034 0.6740 0.056 Uiso 1.00 1 c R
H(27) H -0.5012 0.4727 0.6934 0.056 Uiso 1.00 1 c R
H(28) H -0.5944 0.4478 0.7430 0.056 Uiso 1.00 1 c R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ru(1) 0.0200(2) 0.0228(2) 0.0218(2) -0.0008(2) 0.00503(15) 0.0017(2)
P(1) 0.0210(7) 0.0235(7) 0.0197(7) 0.0002(6) 0.0034(5) 0.0017(6)
F(1) 0.030(2) 0.065(2) 0.034(2) 0.0081(18) -0.0037(15) -0.0126(18)
F(2) 0.048(2) 0.048(2) 0.0278(19) 0.0047(18) -0.0101(16) -0.0166(16)
F(3) 0.056(2) 0.074(2) 0.0176(18) 0.002(2) 0.0063(17) 0.0103(18)
F(4) 0.067(2) 0.041(2) 0.072(2) 0.014(2) -0.028(2) -0.028(2)
F(5) 0.026(2) 0.067(2) 0.065(2) 0.0127(18) -0.0167(18) -0.036(2)
F(6) 0.066(2) 0.119(3) 0.0173(19) -0.012(2) 0.0115(18) -0.020(2)
O(1) 0.044(2) 0.059(3) 0.024(2) 0.013(2) 0.003(2) 0.012(2)
O(2) 0.039(3) 0.064(3) 0.082(3) -0.005(2) 0.031(2) 0.021(3)
O(4) 0.047(2) 0.027(2) 0.042(2) -0.002(2) 0.004(2) -0.009(2)
N(1) 0.046(3) 0.033(3) 0.055(3) 0.008(2) 0.013(2) 0.012(2)
C(1) 0.026(3) 0.031(3) 0.014(2) -0.004(2) 0.002(2) 0.003(2)
C(2) 0.026(2) 0.025(2) 0.018(2) -0.004(2) 0.006(2) -0.001(2)
C(3) 0.017(2) 0.027(2) 0.022(2) -0.004(2) 0.001(2) -0.001(2)
C(4) 0.022(2) 0.026(3) 0.032(3) -0.003(2) 0.006(2) 0.001(2)
C(5) 0.034(3) 0.037(3) 0.021(3) 0.006(2) 0.003(2) -0.002(2)
C(6) 0.019(2) 0.026(3) 0.028(2) 0.000(2) 0.003(2) -0.003(2)
C(7) 0.024(3) 0.029(3) 0.040(3) 0.001(2) 0.007(2) -0.001(2)
C(8) 0.034(3) 0.042(3) 0.011(2) -0.001(2) 0.006(2) 0.000(2)
C(9) 0.020(2) 0.032(3) 0.035(3) 0.000(2) 0.006(2) -0.007(2)
C(10) 0.030(3) 0.026(3) 0.037(3) 0.000(2) 0.001(2) 0.002(2)
C(11) 0.028(3) 0.037(3) 0.017(2) -0.002(2) 0.008(2) -0.002(2)
C(12) 0.031(3) 0.039(3) 0.057(4) 0.002(2) 0.010(3) -0.018(3)
C(13) 0.023(2) 0.027(2) 0.024(2) -0.002(2) 0.001(2) -0.004(2)
C(14) 0.029(3) 0.033(3) 0.019(2) -0.001(2) 0.008(2) -0.003(2)
C(15) 0.019(2) 0.030(3) 0.046(3) -0.000(2) 0.005(2) -0.000(2)
C(16) 0.029(3) 0.030(3) 0.043(3) -0.001(2) -0.002(2) -0.001(2)
C(17) 0.029(3) 0.037(3) 0.038(3) 0.003(2) 0.001(2) 0.004(2)
C(18) 0.027(3) 0.043(3) 0.015(2) 0.004(2) 0.004(2) 0.002(2)
C(19) 0.056(4) 0.058(4) 0.026(3) 0.013(3) -0.002(3) 0.010(3)
C(20) 0.020(3) 0.048(4) 0.041(3) 0.009(2) -0.001(2) -0.008(3)
C(21) 0.026(3) 0.030(3) 0.045(3) -0.000(2) 0.017(2) 0.000(3)
C(22) 0.049(4) 0.026(3) 0.023(3) -0.005(2) 0.009(2) 0.006(2)
C(23) 0.026(3) 0.031(3) 0.023(3) -0.000(2) 0.005(2) 0.010(2)
C(24) 0.019(2) 0.028(2) 0.021(2) -0.001(2) 0.004(2) 0.003(2)
C(25) 0.030(2) 0.034(3) 0.016(2) 0.001(2) 0.005(2) 0.006(2)
C(26) 0.021(2) 0.042(3) 0.050(3) 0.002(2) -0.001(2) 0.012(3)
C(27) 0.034(3) 0.061(4) 0.038(3) -0.006(3) -0.008(3) 0.015(3)
C(28) 0.034(3) 0.046(4) 0.049(4) -0.011(3) -0.003(3) -0.004(3)
C(29) 0.025(3) 0.036(3) 0.043(3) -0.005(2) -0.002(2) 0.003(2)
C(30) 0.020(3) 0.030(3) 0.057(4) 0.003(2) 0.006(2) 0.014(3)
C(31) 0.023(2) 0.028(2) 0.021(2) -0.002(2) 0.002(2) 0.006(2)
C(32) 0.021(2) 0.027(2) 0.040(3) -0.008(2) 0.003(2) 0.006(2)
C(33) 0.028(3) 0.027(3) 0.030(3) -0.003(2) 0.004(2) -0.002(2)
C(34) 0.035(3) 0.031(3) 0.041(3) 0.004(2) 0.007(2) 0.011(2)
C(35) 0.033(3) 0.042(3) 0.055(4) 0.012(3) 0.006(3) 0.022(3)
C(36) 0.040(3) 0.040(3) 0.014(2) 0.005(2) 0.001(2) -0.000(2)
C(37) 0.031(3) 0.033(3) 0.019(2) -0.003(2) 0.010(2) -0.004(2)
C(38) 0.028(3) 0.043(3) 0.019(2) -0.001(2) 0.006(2) -0.001(2)
C(39) 0.038(4) 0.051(4) 0.049(4) 0.004(3) 0.002(3) -0.022(3)
C(40) 0.046(4) 0.074(5) 0.029(3) 0.013(3) 0.014(3) -0.014(3)
C(41) 0.035(3) 0.082(5) 0.021(2) 0.005(4) 0.010(2) -0.007(3)
C(42) 0.029(3) 0.041(3) 0.045(3) -0.008(2) 0.008(2) -0.010(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ru Ru -1.259 0.836
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
P(1) Ru(1) C(1) 91.28(15) yes
P(1) Ru(1) C(4) 90.48(15) yes
P(1) Ru(1) C(21) 93.68(19) yes
P(1) Ru(1) C(22) 169.40(17) yes
P(1) Ru(1) C(23) 93.91(17) yes
C(1) Ru(1) C(4) 75.58(19) yes
C(1) Ru(1) C(21) 95.4(2) yes
C(1) Ru(1) C(22) 81.1(2) yes
C(1) Ru(1) C(23) 173.7(2) yes
C(4) Ru(1) C(21) 170.2(2) yes
C(4) Ru(1) C(22) 80.5(2) yes
C(4) Ru(1) C(23) 100.8(2) yes
C(21) Ru(1) C(22) 94.4(2) yes
C(21) Ru(1) C(23) 87.8(2) yes
C(22) Ru(1) C(23) 93.2(2) yes
Ru(1) P(1) C(24) 111.68(18) yes
Ru(1) P(1) C(31) 115.76(18) yes
Ru(1) P(1) C(37) 117.95(19) yes
C(24) P(1) C(31) 105.2(2) yes
C(24) P(1) C(37) 100.1(2) yes
C(31) P(1) C(37) 104.3(2) yes
Ru(1) C(1) C(2) 118.2(3) yes
Ru(1) C(1) C(5) 121.3(3) yes
C(2) C(1) C(5) 120.2(4) yes
C(1) C(2) C(3) 112.5(4) yes
C(1) C(2) C(6) 126.7(4) yes
C(3) C(2) C(6) 120.6(4) yes
C(2) C(3) C(4) 116.7(4) yes
C(2) C(3) C(13) 117.0(4) yes
C(4) C(3) C(13) 126.3(4) yes
Ru(1) C(4) C(3) 116.5(3) yes
Ru(1) C(4) C(20) 122.7(3) yes
C(3) C(4) C(20) 120.4(4) yes
F(1) C(5) F(2) 103.8(4) yes
F(1) C(5) F(3) 105.4(4) yes
F(1) C(5) C(1) 111.5(4) yes
F(2) C(5) F(3) 106.3(4) yes
F(2) C(5) C(1) 116.8(4) yes
F(3) C(5) C(1) 112.1(4) yes
C(2) C(6) C(7) 119.8(4) yes
C(2) C(6) C(11) 120.9(4) yes
C(7) C(6) C(11) 119.1(5) yes
C(6) C(7) C(8) 121.1(5) yes
C(7) C(8) C(9) 121.0(5) yes
C(8) C(9) C(10) 118.0(5) yes
C(8) C(9) C(12) 121.3(5) yes
C(10) C(9) C(12) 120.8(5) yes
C(9) C(10) C(11) 121.6(5) yes
C(6) C(11) C(10) 119.2(5) yes
C(3) C(13) C(14) 121.8(4) yes
C(3) C(13) C(18) 119.8(5) yes
C(14) C(13) C(18) 118.4(4) yes
C(13) C(14) C(15) 119.9(5) yes
C(14) C(15) C(16) 122.0(5) yes
C(15) C(16) C(17) 119.4(5) yes
C(15) C(16) C(19) 121.1(5) yes
C(17) C(16) C(19) 119.5(5) yes
C(16) C(17) C(18) 118.8(5) yes
C(13) C(18) C(17) 121.3(5) yes
F(4) C(20) F(5) 104.6(4) yes
F(4) C(20) F(6) 104.3(5) yes
F(4) C(20) C(4) 114.0(4) yes
F(5) C(20) F(6) 105.2(4) yes
F(5) C(20) C(4) 116.3(5) yes
F(6) C(20) C(4) 111.4(4) yes
Ru(1) C(21) O(1) 176.2(5) yes
Ru(1) C(22) O(2) 174.1(5) yes
Ru(1) C(23) O(4) 174.5(5) yes
P(1) C(24) C(25) 120.6(3) yes
P(1) C(24) C(29) 122.0(4) yes
C(25) C(24) C(29) 117.1(4) yes
C(24) C(25) C(26) 121.0(5) yes
C(24) C(25) C(30) 123.0(4) yes
C(26) C(25) C(30) 116.1(5) yes
C(25) C(26) C(27) 118.9(5) yes
C(26) C(27) C(28) 122.1(5) yes
C(27) C(28) C(29) 118.4(6) yes
C(24) C(29) C(28) 122.5(5) yes
N(1) C(30) C(25) 177.0(5) yes
P(1) C(31) C(32) 123.2(4) yes
P(1) C(31) C(36) 119.7(4) yes
C(32) C(31) C(36) 117.0(5) yes
C(31) C(32) C(33) 121.6(5) yes
C(32) C(33) C(34) 120.4(5) yes
C(33) C(34) C(35) 118.1(5) yes
C(34) C(35) C(36) 123.2(6) yes
C(31) C(36) C(35) 119.7(5) yes
P(1) C(37) C(38) 122.2(4) yes
P(1) C(37) C(42) 119.9(4) yes
C(38) C(37) C(42) 117.9(5) yes
C(37) C(38) C(39) 121.0(5) yes
C(38) C(39) C(40) 120.1(6) yes
C(39) C(40) C(41) 119.5(6) yes
C(40) C(41) C(42) 120.5(6) yes
C(37) C(42) C(41) 120.8(5) yes
C(6) C(7) H(1) 119.6 no
C(8) C(7) H(1) 119.3 no
C(7) C(8) H(2) 119.7 no
C(9) C(8) H(2) 119.3 no
C(9) C(10) H(3) 119.7 no
C(11) C(10) H(3) 118.7 no
C(6) C(11) H(4) 120.4 no
C(10) C(11) H(4) 120.4 no
C(9) C(12) H(23) 109.3 no
C(9) C(12) H(24) 109.7 no
C(9) C(12) H(25) 109.4 no
H(23) C(12) H(24) 109.5 no
H(23) C(12) H(25) 109.5 no
H(24) C(12) H(25) 109.5 no
C(13) C(14) H(5) 119.7 no
C(15) C(14) H(5) 120.4 no
C(14) C(15) H(6) 118.7 no
C(16) C(15) H(6) 119.2 no
C(16) C(17) H(7) 120.6 no
C(18) C(17) H(7) 120.5 no
C(13) C(18) H(8) 119.3 no
C(17) C(18) H(8) 119.4 no
C(16) C(19) H(26) 109.8 no
C(16) C(19) H(27) 109.7 no
C(16) C(19) H(28) 108.8 no
H(26) C(19) H(27) 109.5 no
H(26) C(19) H(28) 109.5 no
H(27) C(19) H(28) 109.5 no
C(25) C(26) H(9) 120.4 no
C(27) C(26) H(9) 120.7 no
C(26) C(27) H(10) 119.0 no
C(28) C(27) H(10) 119.0 no
C(27) C(28) H(11) 120.7 no
C(29) C(28) H(11) 120.9 no
C(24) C(29) H(12) 118.5 no
C(28) C(29) H(12) 118.9 no
C(31) C(32) H(13) 118.6 no
C(33) C(32) H(13) 119.8 no
C(32) C(33) H(14) 119.6 no
C(34) C(33) H(14) 120.0 no
C(33) C(34) H(15) 120.7 no
C(35) C(34) H(15) 121.2 no
C(34) C(35) H(16) 118.5 no
C(36) C(35) H(16) 118.3 no
C(31) C(36) H(17) 119.7 no
C(35) C(36) H(17) 120.6 no
C(37) C(38) H(18) 118.8 no
C(39) C(38) H(18) 120.2 no
C(38) C(39) H(19) 119.9 no
C(40) C(39) H(19) 120.0 no
C(39) C(40) H(20) 119.9 no
C(41) C(40) H(20) 120.6 no
C(40) C(41) H(21) 119.3 no
C(42) C(41) H(21) 120.2 no
C(37) C(42) H(22) 119.4 no
C(41) C(42) H(22) 119.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ru(1) P(1) 2.4681(15) yes
Ru(1) C(1) 2.155(5) yes
Ru(1) C(4) 2.151(5) yes
Ru(1) C(21) 1.962(6) yes
Ru(1) C(22) 1.961(6) yes
Ru(1) C(23) 1.981(5) yes
P(1) C(24) 1.844(5) yes
P(1) C(31) 1.858(5) yes
P(1) C(37) 1.848(5) yes
F(1) C(5) 1.373(7) yes
F(2) C(5) 1.373(7) yes
F(3) C(5) 1.367(7) yes
F(4) C(20) 1.373(7) yes
F(5) C(20) 1.345(6) yes
F(6) C(20) 1.362(7) yes
O(1) C(21) 1.120(7) yes
O(2) C(22) 1.141(8) yes
O(4) C(23) 1.166(7) yes
N(1) C(30) 1.163(8) yes
C(1) C(2) 1.377(7) yes
C(1) C(5) 1.494(7) yes
C(2) C(3) 1.492(7) yes
C(2) C(6) 1.535(7) yes
C(3) C(4) 1.369(7) yes
C(3) C(13) 1.502(7) yes
C(4) C(20) 1.486(8) yes
C(6) C(7) 1.394(8) yes
C(6) C(11) 1.421(7) yes
C(7) C(8) 1.416(8) yes
C(8) C(9) 1.416(8) yes
C(9) C(10) 1.400(9) yes
C(9) C(12) 1.530(8) yes
C(10) C(11) 1.439(8) yes
C(13) C(14) 1.409(8) yes
C(13) C(18) 1.410(7) yes
C(14) C(15) 1.411(7) yes
C(15) C(16) 1.368(9) yes
C(16) C(17) 1.428(9) yes
C(16) C(19) 1.532(8) yes
C(17) C(18) 1.418(7) yes
C(24) C(25) 1.427(7) yes
C(24) C(29) 1.405(8) yes
C(25) C(26) 1.407(7) yes
C(25) C(30) 1.472(8) yes
C(26) C(27) 1.370(9) yes
C(27) C(28) 1.409(9) yes
C(28) C(29) 1.377(8) yes
C(31) C(32) 1.412(8) yes
C(31) C(36) 1.406(7) yes
C(32) C(33) 1.410(8) yes
C(33) C(34) 1.391(8) yes
C(34) C(35) 1.361(9) yes
C(35) C(36) 1.413(8) yes
C(37) C(38) 1.422(7) yes
C(37) C(42) 1.408(8) yes
C(38) C(39) 1.404(9) yes
C(39) C(40) 1.398(10) yes
C(40) C(41) 1.404(9) yes
C(41) C(42) 1.405(9) yes
C(7) H(1) 0.950 no
C(8) H(2) 0.950 no
C(10) H(3) 0.950 no
C(11) H(4) 0.950 no
C(12) H(23) 0.950 no
C(12) H(24) 0.950 no
C(12) H(25) 0.950 no
C(14) H(5) 0.950 no
C(15) H(6) 0.950 no
C(17) H(7) 0.950 no
C(18) H(8) 0.950 no
C(19) H(26) 0.950 no
C(19) H(27) 0.950 no
C(19) H(28) 0.950 no
C(26) H(9) 0.950 no
C(27) H(10) 0.950 no
C(28) H(11) 0.950 no
C(29) H(12) 0.950 no
C(32) H(13) 0.950 no
C(33) H(14) 0.950 no
C(34) H(15) 0.950 no
C(35) H(16) 0.950 no
C(36) H(17) 0.950 no
C(38) H(18) 0.950 no
C(39) H(19) 0.950 no
C(40) H(20) 0.950 no
C(41) H(21) 0.950 no
C(42) H(22) 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
F(2) F(6) 3.303(5) 4_555
F(2) C(38) 3.495(6) 4_555
F(2) C(39) 3.260(7) 4_555
F(3) F(6) 3.114(5) 4_555
F(3) C(35) 3.373(7) 4_555
F(3) C(36) 3.332(6) 4_555
F(4) C(34) 3.326(7) 2_546
F(5) C(8) 3.559(6) 4_554
F(5) C(41) 3.484(7) 1_455
F(6) F(2) 3.303(5) 4_554
F(6) F(3) 3.114(5) 4_554
F(6) C(7) 3.452(6) 4_554
F(6) C(8) 3.531(6) 4_554
O(1) O(2) 3.471(6) 3_557
O(1) O(4) 3.283(6) 3_557
O(1) C(23) 3.593(7) 3_557
O(2) O(1) 3.471(6) 3_557
O(2) O(4) 3.319(6) 3_557
O(2) N(1) 3.034(7) 3_557
O(2) C(26) 3.594(7) 1_455
O(4) O(1) 3.283(6) 3_557
O(4) O(2) 3.319(6) 3_557
O(4) C(21) 3.484(8) 3_557
O(4) C(22) 3.399(7) 3_557
O(4) C(34) 3.441(7) 2_546
O(4) C(35) 3.378(7) 2_546
N(1) O(2) 3.034(7) 3_557
C(7) F(6) 3.452(6) 4_555
C(7) C(27) 3.554(9) 1_455
C(8) F(5) 3.559(6) 4_555
C(8) F(6) 3.531(6) 4_555
C(8) C(28) 3.474(8) 1_455
C(9) C(33) 3.473(7) 3_567
C(10) C(33) 3.559(7) 3_567
C(12) C(33) 3.536(8) 3_567
C(21) O(4) 3.484(8) 3_557
C(22) O(4) 3.399(7) 3_557
C(23) O(1) 3.593(7) 3_557
C(26) O(2) 3.594(7) 1_655
C(27) C(7) 3.554(9) 1_655
C(28) C(8) 3.474(8) 1_655
C(33) C(9) 3.473(7) 3_567
C(33) C(10) 3.559(7) 3_567
C(33) C(12) 3.536(8) 3_567
C(34) F(4) 3.326(7) 2_556
C(34) O(4) 3.441(7) 2_556
C(35) F(3) 3.373(7) 4_554
C(35) O(4) 3.378(7) 2_556
C(36) F(3) 3.332(6) 4_554
C(38) F(2) 3.495(6) 4_554
C(39) F(2) 3.260(7) 4_554
C(41) F(5) 3.484(7) 1_655
F(1) H(17) 3.195 4_555
F(2) H(18) 3.462 4_555
F(2) H(19) 3.080 4_555
F(3) H(8) 3.491 4_555
F(3) H(16) 2.959 4_555
F(3) H(17) 2.909 4_555
F(4) H(2) 3.383 4_554
F(4) H(15) 2.548 2_546
F(4) H(16) 3.451 2_546
F(5) H(2) 2.730 4_554
F(5) H(21) 2.596 1_455
F(6) H(1) 3.040 4_554
F(6) H(2) 3.173 4_554
O(1) H(16) 2.766 4_555
O(1) H(26) 3.042 4_655
O(2) H(9) 3.038 1_455
O(4) H(7) 3.547 2_546
O(4) H(15) 2.948 2_546
O(4) H(16) 2.779 2_546
N(1) H(7) 2.924 2_546
N(1) H(9) 2.742 3_657
N(1) H(27) 3.007 2_546
C(5) H(17) 3.556 4_555
C(7) H(10) 3.146 1_455
C(7) H(11) 3.264 1_455
C(8) H(10) 3.480 1_455
C(8) H(11) 2.787 1_455
C(9) H(11) 3.421 1_455
C(9) H(14) 3.183 3_567
C(9) H(23) 3.046 3_467
C(10) H(14) 3.021 3_567
C(10) H(20) 3.310 2_556
C(10) H(23) 3.028 3_467
C(11) H(14) 3.570 3_567
C(11) H(19) 3.509 2_556
C(12) H(6) 3.103 3_467
C(12) H(12) 3.295 3_567
C(12) H(23) 3.034 3_467
C(12) H(28) 3.308 3_467
C(14) H(22) 2.992 1_455
C(15) H(22) 2.960 1_455
C(15) H(23) 3.527 3_467
C(15) H(24) 3.456 3_467
C(15) H(25) 3.267 3_467
C(16) H(10) 3.542 4_454
C(16) H(25) 3.508 3_467
C(17) H(10) 3.237 4_454
C(19) H(9) 3.405 4_454
C(19) H(25) 3.239 3_467
C(20) H(2) 3.369 4_554
C(21) H(16) 3.424 4_555
C(23) H(15) 3.514 2_546
C(26) H(26) 3.020 4_655
C(27) H(1) 3.162 1_655
C(27) H(5) 3.456 1_655
C(27) H(26) 3.299 4_655
C(28) H(1) 3.583 1_655
C(28) H(2) 3.364 1_655
C(28) H(5) 3.271 1_655
C(28) H(24) 3.598 3_567
C(29) H(5) 3.362 1_655
C(29) H(6) 3.542 1_655
C(29) H(24) 3.113 3_567
C(30) H(9) 3.591 3_657
C(31) H(24) 3.580 3_567
C(32) H(24) 3.090 3_567
C(33) H(3) 3.543 3_567
C(33) H(24) 3.101 3_567
C(33) H(25) 3.533 3_567
C(34) H(19) 3.493 2_556
C(34) H(24) 3.577 3_567
C(34) H(25) 3.432 3_567
C(35) H(28) 3.465 1_655
C(36) H(6) 3.451 1_655
C(38) H(15) 3.498 2_546
C(39) H(3) 3.499 2_546
C(39) H(15) 3.587 2_546
C(40) H(3) 3.259 2_546
C(40) H(11) 3.419 4_554
C(40) H(27) 3.413 2_546
C(41) H(11) 3.537 4_554
C(41) H(27) 3.422 2_546
C(42) H(6) 3.378 1_655
H(1) F(6) 3.040 4_555
H(1) C(27) 3.162 1_455
H(1) C(28) 3.583 1_455
H(1) H(10) 2.580 1_455
H(1) H(11) 3.377 1_455
H(2) F(4) 3.383 4_555
H(2) F(5) 2.730 4_555
H(2) F(6) 3.173 4_555
H(2) C(20) 3.369 4_555
H(2) C(28) 3.364 1_455
H(2) H(10) 3.235 1_455
H(2) H(11) 2.600 1_455
H(2) H(21) 3.035 4_455
H(3) C(33) 3.543 3_567
H(3) C(39) 3.499 2_556
H(3) C(40) 3.259 2_556
H(3) H(12) 3.294 3_567
H(3) H(13) 3.385 3_567
H(3) H(14) 3.105 3_567
H(3) H(19) 3.027 2_556
H(3) H(20) 2.537 2_556
H(3) H(23) 2.935 3_467
H(4) H(19) 2.815 2_556
H(5) C(27) 3.456 1_455
H(5) C(28) 3.271 1_455
H(5) C(29) 3.362 1_455
H(5) H(22) 2.724 1_455
H(6) C(12) 3.103 3_467
H(6) C(29) 3.542 1_455
H(6) C(36) 3.451 1_455
H(6) C(42) 3.378 1_455
H(6) H(12) 3.339 1_455
H(6) H(17) 3.527 1_455
H(6) H(22) 2.634 1_455
H(6) H(23) 3.237 3_467
H(6) H(24) 2.789 3_467
H(6) H(25) 2.784 3_467
H(7) O(4) 3.547 2_556
H(7) N(1) 2.924 2_556
H(7) H(9) 3.208 4_454
H(7) H(10) 3.154 4_454
H(8) F(3) 3.491 4_554
H(9) O(2) 3.038 1_655
H(9) N(1) 2.742 3_657
H(9) C(19) 3.405 4_655
H(9) C(30) 3.591 3_657
H(9) H(7) 3.208 4_655
H(9) H(26) 2.859 4_655
H(9) H(27) 3.210 4_655
H(10) C(7) 3.146 1_655
H(10) C(8) 3.480 1_655
H(10) C(16) 3.542 4_655
H(10) C(17) 3.237 4_655
H(10) H(1) 2.580 1_655
H(10) H(2) 3.235 1_655
H(10) H(7) 3.154 4_655
H(10) H(26) 3.289 4_655
H(11) C(7) 3.264 1_655
H(11) C(8) 2.787 1_655
H(11) C(9) 3.421 1_655
H(11) C(40) 3.419 4_555
H(11) C(41) 3.537 4_555
H(11) H(1) 3.377 1_655
H(11) H(2) 2.600 1_655
H(11) H(20) 2.959 4_555
H(11) H(21) 3.157 4_555
H(11) H(23) 3.548 1_655
H(11) H(24) 3.347 3_567
H(12) C(12) 3.295 3_567
H(12) H(3) 3.294 3_567
H(12) H(6) 3.339 1_655
H(12) H(24) 2.354 3_567
H(13) H(3) 3.385 3_567
H(13) H(24) 3.306 3_567
H(14) C(9) 3.183 3_567
H(14) C(10) 3.021 3_567
H(14) C(11) 3.570 3_567
H(14) H(3) 3.105 3_567
H(14) H(19) 3.204 2_556
H(14) H(24) 3.321 3_567
H(15) F(4) 2.548 2_556
H(15) O(4) 2.948 2_556
H(15) C(23) 3.514 2_556
H(15) C(38) 3.498 2_556
H(15) C(39) 3.587 2_556
H(15) H(18) 2.837 2_556
H(15) H(19) 3.007 2_556
H(16) F(3) 2.959 4_554
H(16) F(4) 3.451 2_556
H(16) O(1) 2.766 4_554
H(16) O(4) 2.779 2_556
H(16) C(21) 3.424 4_554
H(16) H(26) 3.554 1_655
H(16) H(28) 3.321 1_655
H(17) F(1) 3.195 4_554
H(17) F(3) 2.909 4_554
H(17) C(5) 3.556 4_554
H(17) H(6) 3.527 1_655
H(18) F(2) 3.462 4_554
H(18) H(15) 2.837 2_546
H(19) F(2) 3.080 4_554
H(19) C(11) 3.509 2_546
H(19) C(34) 3.493 2_546
H(19) H(3) 3.027 2_546
H(19) H(4) 2.815 2_546
H(19) H(14) 3.204 2_546
H(19) H(15) 3.007 2_546
H(20) C(10) 3.310 2_546
H(20) H(3) 2.537 2_546
H(20) H(11) 2.959 4_554
H(20) H(23) 3.084 4_654
H(20) H(25) 3.301 4_654
H(20) H(27) 3.482 2_546
H(21) F(5) 2.596 1_655
H(21) H(2) 3.035 4_654
H(21) H(11) 3.157 4_554
H(21) H(27) 3.510 2_546
H(22) C(14) 2.992 1_655
H(22) C(15) 2.960 1_655
H(22) H(5) 2.724 1_655
H(22) H(6) 2.634 1_655
H(23) C(9) 3.046 3_467
H(23) C(10) 3.028 3_467
H(23) C(12) 3.034 3_467
H(23) C(15) 3.527 3_467
H(23) H(3) 2.935 3_467
H(23) H(6) 3.237 3_467
H(23) H(11) 3.548 1_455
H(23) H(20) 3.084 4_455
H(23) H(23) 2.424 3_467
H(23) H(24) 3.295 3_467
H(24) C(15) 3.456 3_467
H(24) C(28) 3.598 3_567
H(24) C(29) 3.113 3_567
H(24) C(31) 3.580 3_567
H(24) C(32) 3.090 3_567
H(24) C(33) 3.101 3_567
H(24) C(34) 3.577 3_567
H(24) H(6) 2.789 3_467
H(24) H(11) 3.347 3_567
H(24) H(12) 2.354 3_567
H(24) H(13) 3.306 3_567
H(24) H(14) 3.321 3_567
H(24) H(23) 3.295 3_467
H(24) H(28) 3.571 3_467
H(25) C(15) 3.267 3_467
H(25) C(16) 3.508 3_467
H(25) C(19) 3.239 3_467
H(25) C(33) 3.533 3_567
H(25) C(34) 3.432 3_567
H(25) H(6) 2.784 3_467
H(25) H(20) 3.301 4_455
H(25) H(28) 2.418 3_467
H(26) O(1) 3.042 4_454
H(26) C(26) 3.020 4_454
H(26) C(27) 3.299 4_454
H(26) H(9) 2.859 4_454
H(26) H(10) 3.289 4_454
H(26) H(16) 3.554 1_455
H(27) N(1) 3.007 2_556
H(27) C(40) 3.413 2_556
H(27) C(41) 3.422 2_556
H(27) H(9) 3.210 4_454
H(27) H(20) 3.482 2_556
H(27) H(21) 3.510 2_556
H(28) C(12) 3.308 3_467
H(28) C(35) 3.465 1_455
H(28) H(16) 3.321 1_455
H(28) H(24) 3.571 3_467
H(28) H(25) 2.418 3_467
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
P(1) Ru(1) C(1) C(2) 96.2(4)
P(1) Ru(1) C(1) C(5) -90.3(4)
C(1) Ru(1) P(1) C(24) 81.8(2)
C(1) Ru(1) P(1) C(31) -38.6(2)
C(1) Ru(1) P(1) C(37) -163.1(2)
P(1) Ru(1) C(4) C(3) -94.0(4)
P(1) Ru(1) C(4) C(20) 93.0(4)
C(4) Ru(1) P(1) C(24) 157.3(2)
C(4) Ru(1) P(1) C(31) 37.0(2)
C(4) Ru(1) P(1) C(37) -87.6(2)
P(1) Ru(1) C(21) O(1) -149(8)
C(21) Ru(1) P(1) C(24) -13.8(2)
C(21) Ru(1) P(1) C(31) -134.1(2)
C(21) Ru(1) P(1) C(37) 101.3(2)
P(1) Ru(1) C(22) O(2) 21(5)
C(22) Ru(1) P(1) C(24) 125.9(9)
C(22) Ru(1) P(1) C(31) 5.6(9)
C(22) Ru(1) P(1) C(37) -119.0(9)
P(1) Ru(1) C(23) O(4) 146(4)
C(23) Ru(1) P(1) C(24) -101.8(2)
C(23) Ru(1) P(1) C(31) 137.8(2)
C(23) Ru(1) P(1) C(37) 13.3(2)
C(1) Ru(1) C(4) C(3) -2.8(4)
C(1) Ru(1) C(4) C(20) -175.8(5)
C(4) Ru(1) C(1) C(2) 6.1(4)
C(4) Ru(1) C(1) C(5) 179.5(5)
C(1) Ru(1) C(21) O(1) 120(8)
C(21) Ru(1) C(1) C(2) -169.9(4)
C(21) Ru(1) C(1) C(5) 3.5(4)
C(1) Ru(1) C(22) O(2) 66(5)
C(22) Ru(1) C(1) C(2) -76.3(4)
C(22) Ru(1) C(1) C(5) 97.1(4)
C(1) Ru(1) C(23) O(4) -69(5)
C(23) Ru(1) C(1) C(2) -49(2)
C(23) Ru(1) C(1) C(5) 124.3(18)
C(4) Ru(1) C(21) O(1) 96(8)
C(21) Ru(1) C(4) C(3) 21.2(16)
C(21) Ru(1) C(4) C(20) -151.8(12)
C(4) Ru(1) C(22) O(2) -11(5)
C(22) Ru(1) C(4) C(3) 80.4(4)
C(22) Ru(1) C(4) C(20) -92.6(5)
C(4) Ru(1) C(23) O(4) -123(4)
C(23) Ru(1) C(4) C(3) 172.0(4)
C(23) Ru(1) C(4) C(20) -1.0(5)
C(21) Ru(1) C(22) O(2) 161(5)
C(22) Ru(1) C(21) O(1) 38(8)
C(21) Ru(1) C(23) O(4) 52(4)
C(23) Ru(1) C(21) O(1) -55(8)
C(22) Ru(1) C(23) O(4) -42(4)
C(23) Ru(1) C(22) O(2) -111(5)
Ru(1) P(1) C(24) C(25) 68.8(4)
Ru(1) P(1) C(24) C(29) -105.2(4)
Ru(1) P(1) C(31) C(32) 57.4(4)
Ru(1) P(1) C(31) C(36) -120.0(4)
Ru(1) P(1) C(37) C(38) 29.2(5)
Ru(1) P(1) C(37) C(42) -152.6(4)
C(24) P(1) C(31) C(32) -66.4(5)
C(24) P(1) C(31) C(36) 116.2(4)
C(31) P(1) C(24) C(25) -164.9(4)
C(31) P(1) C(24) C(29) 21.1(5)
C(24) P(1) C(37) C(38) 150.4(4)
C(24) P(1) C(37) C(42) -31.3(5)
C(37) P(1) C(24) C(25) -56.9(5)
C(37) P(1) C(24) C(29) 129.1(5)
C(31) P(1) C(37) C(38) -100.9(4)
C(31) P(1) C(37) C(42) 77.4(5)
C(37) P(1) C(31) C(32) -171.3(4)
C(37) P(1) C(31) C(36) 11.3(5)
Ru(1) C(1) C(2) C(3) -8.0(6)
Ru(1) C(1) C(2) C(6) 168.2(4)
Ru(1) C(1) C(5) F(1) 42.3(6)
Ru(1) C(1) C(5) F(2) 161.4(3)
Ru(1) C(1) C(5) F(3) -75.6(5)
C(2) C(1) C(5) F(1) -144.4(5)
C(2) C(1) C(5) F(2) -25.3(8)
C(2) C(1) C(5) F(3) 97.7(6)
C(5) C(1) C(2) C(3) 178.5(5)
C(5) C(1) C(2) C(6) -5.3(8)
C(1) C(2) C(3) C(4) 5.4(7)
C(1) C(2) C(3) C(13) -175.9(4)
C(1) C(2) C(6) C(7) -55.8(7)
C(1) C(2) C(6) C(11) 129.5(6)
C(3) C(2) C(6) C(7) 120.0(5)
C(3) C(2) C(6) C(11) -54.7(7)
C(6) C(2) C(3) C(4) -171.0(5)
C(6) C(2) C(3) C(13) 7.7(7)
C(2) C(3) C(4) Ru(1) -0.5(6)
C(2) C(3) C(4) C(20) 172.7(5)
C(2) C(3) C(13) C(14) -69.7(6)
C(2) C(3) C(13) C(18) 110.5(6)
C(4) C(3) C(13) C(14) 108.7(6)
C(4) C(3) C(13) C(18) -71.1(7)
C(13) C(3) C(4) Ru(1) -178.9(4)
C(13) C(3) C(4) C(20) -5.8(9)
Ru(1) C(4) C(20) F(4) 20.3(7)
Ru(1) C(4) C(20) F(5) 142.1(4)
Ru(1) C(4) C(20) F(6) -97.3(5)
C(3) C(4) C(20) F(4) -152.4(5)
C(3) C(4) C(20) F(5) -30.6(8)
C(3) C(4) C(20) F(6) 90.0(6)
C(2) C(6) C(7) C(8) -176.2(4)
C(2) C(6) C(11) C(10) 175.8(4)
C(7) C(6) C(11) C(10) 1.1(7)
C(11) C(6) C(7) C(8) -1.4(7)
C(6) C(7) C(8) C(9) 2.2(8)
C(7) C(8) C(9) C(10) -2.7(8)
C(7) C(8) C(9) C(12) 177.7(5)
C(8) C(9) C(10) C(11) 2.4(8)
C(12) C(9) C(10) C(11) -178.0(5)
C(9) C(10) C(11) C(6) -1.6(8)
C(3) C(13) C(14) C(15) -178.5(5)
C(3) C(13) C(18) C(17) 179.9(3)
C(14) C(13) C(18) C(17) 0.1(6)
C(18) C(13) C(14) C(15) 1.3(8)
C(13) C(14) C(15) C(16) -2.9(8)
C(14) C(15) C(16) C(17) 3.1(8)
C(14) C(15) C(16) C(19) -178.8(5)
C(15) C(16) C(17) C(18) -1.6(8)
C(19) C(16) C(17) C(18) -179.8(5)
C(16) C(17) C(18) C(13) 0.0(7)
P(1) C(24) C(25) C(26) -173.3(4)
P(1) C(24) C(25) C(30) 7.6(7)
P(1) C(24) C(29) C(28) 173.9(5)
C(25) C(24) C(29) C(28) -0.3(7)
C(29) C(24) C(25) C(26) 1.0(8)
C(29) C(24) C(25) C(30) -178.2(5)
C(24) C(25) C(26) C(27) -0.7(9)
C(24) C(25) C(30) N(1) -176(10)
C(26) C(25) C(30) N(1) 5(10)
C(30) C(25) C(26) C(27) 178.5(5)
C(25) C(26) C(27) C(28) -0.4(9)
C(26) C(27) C(28) C(29) 1.1(10)
C(27) C(28) C(29) C(24) -0.7(10)
P(1) C(31) C(32) C(33) -177.3(4)
P(1) C(31) C(36) C(35) 177.9(4)
C(32) C(31) C(36) C(35) 0.4(6)
C(36) C(31) C(32) C(33) 0.1(6)
C(31) C(32) C(33) C(34) -0.4(7)
C(32) C(33) C(34) C(35) 0.2(6)
C(33) C(34) C(35) C(36) 0.3(7)
C(34) C(35) C(36) C(31) -0.6(9)
P(1) C(37) C(38) C(39) -177.3(4)
P(1) C(37) C(42) C(41) 178.6(4)
C(38) C(37) C(42) C(41) -3.0(8)
C(42) C(37) C(38) C(39) 4.4(8)
C(37) C(38) C(39) C(40) -4.0(9)
C(38) C(39) C(40) C(41) 2.2(10)
C(39) C(40) C(41) C(42) -0.9(10)
C(40) C(41) C(42) C(37) 1.4(10)
|
1501958.cif | #------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/19/1501958.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501958
loop_
_publ_author_name
'Zhu, Yuanxun'
'Yin, Guangwei'
'Hong, Deng'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
Tandem reaction of propargylic alcohol, sulfonamide, and
N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1024
_journal_page_last 1027
_journal_paper_doi 10.1021/ol103074d
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C28 H22 I N O2 S'
_chemical_formula_sum 'C28 H22 I N O2 S'
_chemical_formula_weight 563.43
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 76.252(5)
_cell_angle_beta 68.044(6)
_cell_angle_gamma 75.371(5)
_cell_formula_units_Z 2
_cell_length_a 10.0605(6)
_cell_length_b 11.3570(6)
_cell_length_c 11.6434(7)
_cell_measurement_reflns_used 3253
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.3196
_cell_measurement_theta_min 3.4480
_cell_volume 1178.55(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0283
_diffrn_reflns_av_sigmaI/netI 0.0729
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 7792
_diffrn_reflns_theta_full 25.35
_diffrn_reflns_theta_max 25.35
_diffrn_reflns_theta_min 3.45
_exptl_absorpt_coefficient_mu 1.473
_exptl_absorpt_correction_T_max 0.915
_exptl_absorpt_correction_T_min 0.781
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET)
(compiled Nov 17 2009,16:58:22)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.588
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 564
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.524
_refine_diff_density_min -0.431
_refine_diff_density_rms 0.066
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.853
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 299
_refine_ls_number_reflns 4296
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.853
_refine_ls_R_factor_all 0.0581
_refine_ls_R_factor_gt 0.0325
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0175P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0496
_refine_ls_wR_factor_ref 0.0525
_reflns_number_gt 2945
_reflns_number_total 4296
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103074d_si_002.cif
_cod_data_source_block 100514_zyx126
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'multi-scan'' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.
Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius
;
_cod_original_cell_volume 1178.54(12)
_cod_database_code 1501958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.60566(3) 0.57248(2) 0.61158(2) 0.04884(10) Uani 1 1 d .
S S 0.26989(8) 0.61766(7) 0.99057(7) 0.0303(2) Uani 1 1 d .
O1 O 0.1674(2) 0.71702(19) 1.04695(19) 0.0408(6) Uani 1 1 d .
O2 O 0.3168(2) 0.51073(18) 1.07001(19) 0.0401(6) Uani 1 1 d .
N N 0.4197(2) 0.6646(2) 0.9020(2) 0.0290(6) Uani 1 1 d .
H H 0.4961 0.6236 0.9195 0.035 Uiso 1 1 calc R
C1 C 0.2239(4) 0.7645(3) 0.5043(3) 0.0459(9) Uani 1 1 d .
H1 H 0.1505 0.7512 0.5811 0.055 Uiso 1 1 calc R
C2 C 0.2050(5) 0.7544(3) 0.3953(4) 0.0631(12) Uani 1 1 d .
H2 H 0.1205 0.7318 0.3992 0.076 Uiso 1 1 calc R
C3 C 0.3111(5) 0.7776(3) 0.2817(4) 0.0655(13) Uani 1 1 d .
H3 H 0.2985 0.7713 0.2083 0.079 Uiso 1 1 calc R
C4 C 0.4350(5) 0.8101(4) 0.2764(3) 0.0626(12) Uani 1 1 d .
H4 H 0.5064 0.8270 0.1992 0.075 Uiso 1 1 calc R
C5 C 0.4550(4) 0.8179(3) 0.3851(3) 0.0476(9) Uani 1 1 d .
H5 H 0.5401 0.8397 0.3806 0.057 Uiso 1 1 calc R
C6 C 0.3506(3) 0.7940(3) 0.4998(3) 0.0322(8) Uani 1 1 d .
C7 C 0.3692(3) 0.8026(3) 0.6178(3) 0.0282(7) Uani 1 1 d .
C8 C 0.2818(3) 0.8975(3) 0.6967(3) 0.0288(7) Uani 1 1 d .
C9 C 0.1757(3) 0.9973(3) 0.6791(3) 0.0370(8) Uani 1 1 d .
H9 H 0.1498 1.0126 0.6075 0.044 Uiso 1 1 calc R
C10 C 0.1086(3) 1.0739(3) 0.7679(3) 0.0436(9) Uani 1 1 d .
H10 H 0.0364 1.1407 0.7567 0.052 Uiso 1 1 calc R
C11 C 0.1483(3) 1.0517(3) 0.8738(3) 0.0419(9) Uani 1 1 d .
H11 H 0.1021 1.1038 0.9336 0.050 Uiso 1 1 calc R
C12 C 0.2550(3) 0.9537(3) 0.8921(3) 0.0355(8) Uani 1 1 d .
H12 H 0.2824 0.9401 0.9628 0.043 Uiso 1 1 calc R
C13 C 0.3209(3) 0.8756(3) 0.8036(3) 0.0264(7) Uani 1 1 d .
C14 C 0.4464(3) 0.7661(3) 0.7962(3) 0.0264(7) Uani 1 1 d .
C15 C 0.4629(3) 0.7282(3) 0.6727(3) 0.0284(7) Uani 1 1 d .
C16 C 0.5814(3) 0.8100(3) 0.7917(3) 0.0290(7) Uani 1 1 d .
C17 C 0.6818(4) 0.8530(3) 0.6813(3) 0.0448(9) Uani 1 1 d .
H17 H 0.6722 0.8518 0.6052 0.054 Uiso 1 1 calc R
C18 C 0.7963(4) 0.8977(3) 0.6820(4) 0.0548(10) Uani 1 1 d .
H18 H 0.8634 0.9262 0.6065 0.066 Uiso 1 1 calc R
C19 C 0.8126(4) 0.9006(3) 0.7930(4) 0.0524(10) Uani 1 1 d .
H19 H 0.8898 0.9316 0.7929 0.063 Uiso 1 1 calc R
C20 C 0.7153(4) 0.8580(3) 0.9027(4) 0.0495(10) Uani 1 1 d .
H20 H 0.7267 0.8585 0.9783 0.059 Uiso 1 1 calc R
C21 C 0.5992(3) 0.8138(3) 0.9028(3) 0.0407(9) Uani 1 1 d .
H21 H 0.5321 0.7863 0.9788 0.049 Uiso 1 1 calc R
C22 C 0.1965(3) 0.5701(3) 0.8973(3) 0.0291(7) Uani 1 1 d .
C23 C 0.0677(3) 0.6348(3) 0.8813(3) 0.0375(8) Uani 1 1 d .
H23 H 0.0202 0.7052 0.9178 0.045 Uiso 1 1 calc R
C24 C 0.0095(4) 0.5949(3) 0.8109(3) 0.0424(9) Uani 1 1 d .
H24 H -0.0784 0.6383 0.8014 0.051 Uiso 1 1 calc R
C25 C 0.0782(3) 0.4918(3) 0.7541(3) 0.0357(8) Uani 1 1 d .
C26 C 0.2074(4) 0.4278(3) 0.7721(3) 0.0465(9) Uani 1 1 d .
H26 H 0.2556 0.3579 0.7349 0.056 Uiso 1 1 calc R
C27 C 0.2657(3) 0.4655(3) 0.8438(3) 0.0457(9) Uani 1 1 d .
H27 H 0.3516 0.4205 0.8562 0.055 Uiso 1 1 calc R
C28 C 0.0141(4) 0.4515(3) 0.6756(3) 0.0565(10) Uani 1 1 d .
H28B H 0.0047 0.5167 0.6078 0.085 Uiso 1 1 calc R
H28C H -0.0803 0.4323 0.7265 0.085 Uiso 1 1 calc R
H28A H 0.0767 0.3796 0.6422 0.085 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.05131(16) 0.04840(16) 0.04348(16) -0.02129(12) -0.01784(12) 0.01288(11)
S 0.0284(5) 0.0352(5) 0.0273(5) -0.0040(4) -0.0100(4) -0.0061(4)
O1 0.0361(13) 0.0443(14) 0.0404(14) -0.0185(12) -0.0068(11) -0.0029(11)
O2 0.0396(13) 0.0437(14) 0.0356(14) 0.0097(11) -0.0190(12) -0.0102(11)
N 0.0236(14) 0.0357(16) 0.0320(16) -0.0004(13) -0.0144(12) -0.0095(12)
C1 0.056(2) 0.051(2) 0.040(2) -0.0010(18) -0.026(2) -0.0175(19)
C2 0.088(3) 0.056(3) 0.074(3) -0.010(2) -0.060(3) -0.015(2)
C3 0.103(4) 0.057(3) 0.047(3) -0.024(2) -0.044(3) 0.012(3)
C4 0.073(3) 0.076(3) 0.033(2) -0.016(2) -0.019(2) 0.007(2)
C5 0.050(2) 0.056(2) 0.036(2) -0.0099(19) -0.018(2) -0.0011(19)
C6 0.040(2) 0.0293(19) 0.031(2) -0.0060(15) -0.0187(17) -0.0005(15)
C7 0.0282(17) 0.0320(18) 0.0268(18) -0.0033(15) -0.0104(15) -0.0091(14)
C8 0.0247(17) 0.0292(18) 0.0322(19) -0.0071(15) -0.0079(15) -0.0047(14)
C9 0.0375(19) 0.039(2) 0.038(2) -0.0022(17) -0.0229(18) -0.0006(16)
C10 0.040(2) 0.036(2) 0.057(3) -0.0100(18) -0.025(2) 0.0059(16)
C11 0.036(2) 0.039(2) 0.050(2) -0.0212(18) -0.0111(19) 0.0027(16)
C12 0.039(2) 0.0368(19) 0.037(2) -0.0124(16) -0.0171(17) -0.0036(16)
C13 0.0285(17) 0.0260(17) 0.0254(18) -0.0028(14) -0.0093(15) -0.0069(14)
C14 0.0288(17) 0.0273(17) 0.0242(18) -0.0054(14) -0.0113(15) -0.0019(14)
C15 0.0280(17) 0.0292(18) 0.0283(19) -0.0079(15) -0.0102(15) -0.0014(14)
C16 0.0295(18) 0.0238(17) 0.033(2) -0.0034(15) -0.0106(16) -0.0049(14)
C17 0.044(2) 0.049(2) 0.043(2) 0.0048(18) -0.021(2) -0.0129(18)
C18 0.042(2) 0.060(3) 0.057(3) 0.017(2) -0.016(2) -0.0259(19)
C19 0.044(2) 0.044(2) 0.080(3) -0.002(2) -0.031(2) -0.0160(18)
C20 0.050(2) 0.055(2) 0.059(3) -0.015(2) -0.030(2) -0.012(2)
C21 0.038(2) 0.051(2) 0.039(2) -0.0140(18) -0.0121(17) -0.0117(17)
C22 0.0253(17) 0.0338(19) 0.0294(19) -0.0045(15) -0.0087(15) -0.0086(15)
C23 0.0321(19) 0.035(2) 0.047(2) -0.0079(17) -0.0172(18) -0.0013(15)
C24 0.041(2) 0.044(2) 0.050(2) -0.0003(18) -0.0280(19) -0.0076(17)
C25 0.038(2) 0.046(2) 0.031(2) -0.0021(17) -0.0135(17) -0.0213(17)
C26 0.045(2) 0.050(2) 0.052(2) -0.0238(19) -0.019(2) -0.0026(18)
C27 0.033(2) 0.050(2) 0.058(2) -0.019(2) -0.0212(19) 0.0041(17)
C28 0.057(2) 0.076(3) 0.047(3) -0.011(2) -0.020(2) -0.024(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S O2 118.73(13)
O1 S N 109.47(13)
O2 S N 103.37(12)
O1 S C22 107.87(12)
O2 S C22 108.19(13)
N S C22 108.87(13)
C14 N S 130.20(19)
C14 N H 114.9
S N H 114.9
C6 C1 C2 120.5(4)
C6 C1 H1 119.8
C2 C1 H1 119.8
C3 C2 C1 119.9(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 119.9(3)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.2(4)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 120.8(4)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 118.8(3)
C5 C6 C7 121.7(3)
C1 C6 C7 119.5(3)
C15 C7 C8 108.1(2)
C15 C7 C6 128.0(3)
C8 C7 C6 123.9(2)
C9 C8 C13 119.9(2)
C9 C8 C7 130.7(3)
C13 C8 C7 109.5(2)
C10 C9 C8 119.8(3)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 120.0(3)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 121.0(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 118.9(3)
C11 C12 H12 120.5
C13 C12 H12 120.5
C12 C13 C8 120.4(3)
C12 C13 C14 129.9(3)
C8 C13 C14 109.5(2)
N C14 C13 115.3(2)
N C14 C15 112.2(2)
C13 C14 C15 100.6(2)
N C14 C16 106.5(2)
C13 C14 C16 109.0(2)
C15 C14 C16 113.4(2)
C7 C15 C14 112.3(2)
C7 C15 I1 126.1(2)
C14 C15 I1 121.46(19)
C17 C16 C21 117.8(3)
C17 C16 C14 122.8(3)
C21 C16 C14 119.3(3)
C18 C17 C16 120.8(3)
C18 C17 H17 119.6
C16 C17 H17 119.6
C19 C18 C17 120.6(4)
C19 C18 H18 119.7
C17 C18 H18 119.7
C20 C19 C18 119.5(3)
C20 C19 H19 120.3
C18 C19 H19 120.3
C19 C20 C21 120.3(3)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C16 121.0(3)
C20 C21 H21 119.5
C16 C21 H21 119.5
C23 C22 C27 119.9(3)
C23 C22 S 120.2(2)
C27 C22 S 119.9(2)
C22 C23 C24 119.6(3)
C22 C23 H23 120.2
C24 C23 H23 120.2
C23 C24 C25 121.6(3)
C23 C24 H24 119.2
C25 C24 H24 119.2
C24 C25 C26 117.8(3)
C24 C25 C28 120.6(3)
C26 C25 C28 121.6(3)
C27 C26 C25 121.2(3)
C27 C26 H26 119.4
C25 C26 H26 119.4
C26 C27 C22 119.8(3)
C26 C27 H27 120.1
C22 C27 H27 120.1
C25 C28 H28B 109.5
C25 C28 H28C 109.5
H28B C28 H28C 109.5
C25 C28 H28A 109.5
H28B C28 H28A 109.5
H28C C28 H28A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C15 2.061(3)
S O1 1.4233(19)
S O2 1.434(2)
S N 1.613(2)
S C22 1.759(3)
N C14 1.467(4)
N H 0.8600
C1 C6 1.377(4)
C1 C2 1.386(4)
C1 H1 0.9300
C2 C3 1.371(5)
C2 H2 0.9300
C3 C4 1.363(5)
C3 H3 0.9300
C4 C5 1.379(4)
C4 H4 0.9300
C5 C6 1.372(4)
C5 H5 0.9300
C6 C7 1.482(4)
C7 C15 1.342(4)
C7 C8 1.473(4)
C8 C9 1.381(4)
C8 C13 1.392(4)
C9 C10 1.375(4)
C9 H9 0.9300
C10 C11 1.383(4)
C10 H10 0.9300
C11 C12 1.376(4)
C11 H11 0.9300
C12 C13 1.383(4)
C12 H12 0.9300
C13 C14 1.524(4)
C14 C15 1.536(4)
C14 C16 1.541(4)
C16 C17 1.376(4)
C16 C21 1.382(4)
C17 C18 1.374(4)
C17 H17 0.9300
C18 C19 1.370(5)
C18 H18 0.9300
C19 C20 1.355(5)
C19 H19 0.9300
C20 C21 1.382(4)
C20 H20 0.9300
C21 H21 0.9300
C22 C23 1.374(4)
C22 C27 1.376(4)
C23 C24 1.375(4)
C23 H23 0.9300
C24 C25 1.379(4)
C24 H24 0.9300
C25 C26 1.384(4)
C25 C28 1.501(4)
C26 C27 1.375(4)
C26 H26 0.9300
C27 H27 0.9300
C28 H28B 0.9600
C28 H28C 0.9600
C28 H28A 0.9600
|
1501959.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501959.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501959
loop_
_publ_author_name
'Zhu, Yuanxun'
'Yin, Guangwei'
'Hong, Deng'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
Tandem reaction of propargylic alcohol, sulfonamide, and
N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1024
_journal_page_last 1027
_journal_paper_doi 10.1021/ol103074d
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C29 H23 Cl I N O3 S'
_chemical_formula_sum 'C29 H23 Cl I N O3 S'
_chemical_formula_weight 627.89
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 89.032(3)
_cell_angle_beta 85.245(3)
_cell_angle_gamma 72.767(4)
_cell_formula_units_Z 4
_cell_length_a 13.5075(6)
_cell_length_b 14.2341(7)
_cell_length_c 14.5006(5)
_cell_measurement_reflns_used 5506
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.3266
_cell_measurement_theta_min 2.7779
_cell_volume 2653.6(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0252
_diffrn_reflns_av_sigmaI/netI 0.0451
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 18501
_diffrn_reflns_theta_full 25.35
_diffrn_reflns_theta_max 25.35
_diffrn_reflns_theta_min 2.78
_exptl_absorpt_coefficient_mu 1.418
_exptl_absorpt_correction_T_max 0.753
_exptl_absorpt_correction_T_min 0.606
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET)
(compiled Nov 17 2009,16:58:22)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.572
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 1256
_exptl_crystal_size_max 0.46
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.613
_refine_diff_density_min -0.644
_refine_diff_density_rms 0.066
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 653
_refine_ls_number_reflns 9704
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.020
_refine_ls_R_factor_all 0.0660
_refine_ls_R_factor_gt 0.0375
_refine_ls_shift/su_max 0.062
_refine_ls_shift/su_mean 0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+1.0133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0732
_refine_ls_wR_factor_ref 0.0876
_reflns_number_gt 6695
_reflns_number_total 9704
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103074d_si_003.cif
_cod_data_source_block 100901_zyx175
_cod_original_cell_volume 2653.59(19)
_cod_database_code 1501959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.64153(2) -0.281172(19) 0.057180(18) 0.06210(10) Uani 1 1 d .
I2 I 0.63983(2) 0.709503(19) 0.555876(18) 0.06124(10) Uani 1 1 d .
Cl1 Cl 0.78018(12) -0.74261(8) -0.17852(9) 0.0921(4) Uani 1 1 d .
Cl2 Cl 0.79829(12) 1.08802(8) 0.30859(10) 0.0989(5) Uani 1 1 d .
S1 S 0.54909(7) -0.07029(7) -0.15006(7) 0.0519(2) Uani 1 1 d .
S2 S 0.54811(7) 0.55134(7) 0.35124(7) 0.0481(2) Uani 1 1 d .
O1 O 0.9289(2) -0.0882(2) -0.37870(18) 0.0690(8) Uani 1 1 d .
O2 O 0.5565(2) -0.16417(18) -0.18718(19) 0.0626(7) Uani 1 1 d .
O3 O 0.4535(2) -0.0152(2) -0.09997(19) 0.0680(8) Uani 1 1 d .
O4 O 0.9260(2) 0.3582(2) 0.12787(18) 0.0643(7) Uani 1 1 d .
O5 O 0.5588(2) 0.63890(17) 0.30891(19) 0.0608(7) Uani 1 1 d .
O6 O 0.45171(19) 0.5532(2) 0.40200(18) 0.0636(7) Uani 1 1 d .
N1 N 0.6378(2) -0.0782(2) -0.0791(2) 0.0493(8) Uani 1 1 d .
H1 H 0.6254 -0.0337 -0.0367 0.059 Uiso 1 1 calc R
N2 N 0.6351(2) 0.5105(2) 0.42386(19) 0.0444(7) Uani 1 1 d .
H2A H 0.6213 0.4740 0.4680 0.053 Uiso 1 1 calc R
C1 C 0.9130(4) 0.0114(3) -0.3559(3) 0.0815(14) Uani 1 1 d .
H1C H 0.9415 0.0427 -0.4061 0.122 Uiso 1 1 calc R
H1B H 0.9468 0.0154 -0.3010 0.122 Uiso 1 1 calc R
H1A H 0.8398 0.0438 -0.3451 0.122 Uiso 1 1 calc R
C2 C 0.8755(3) -0.3066(3) -0.2850(2) 0.0528(10) Uani 1 1 d .
H2 H 0.8907 -0.3725 -0.3018 0.063 Uiso 1 1 calc R
C3 C 0.9122(3) -0.2429(3) -0.3407(2) 0.0564(10) Uani 1 1 d .
H3 H 0.9529 -0.2664 -0.3952 0.068 Uiso 1 1 calc R
C4 C 0.8893(3) -0.1441(3) -0.3168(3) 0.0527(10) Uani 1 1 d .
C5 C 0.8312(3) -0.1090(3) -0.2342(2) 0.0497(9) Uani 1 1 d .
H5 H 0.8168 -0.0435 -0.2166 0.060 Uiso 1 1 calc R
C6 C 0.7956(3) -0.1734(3) -0.1792(2) 0.0435(9) Uani 1 1 d .
C7 C 0.8155(3) -0.2714(3) -0.2035(2) 0.0452(9) Uani 1 1 d .
C8 C 0.7685(3) -0.3226(2) -0.1306(2) 0.0445(9) Uani 1 1 d .
C9 C 0.7257(3) -0.2579(3) -0.0625(2) 0.0466(9) Uani 1 1 d .
C10 C 0.7377(3) -0.1557(2) -0.0821(2) 0.0442(9) Uani 1 1 d .
C11 C 0.7683(3) -0.4253(3) -0.1390(2) 0.0477(9) Uani 1 1 d .
C12 C 0.7266(3) -0.4551(3) -0.2140(3) 0.0617(11) Uani 1 1 d .
H12 H 0.6965 -0.4086 -0.2572 0.074 Uiso 1 1 calc R
C13 C 0.7286(3) -0.5514(3) -0.2258(3) 0.0622(11) Uani 1 1 d .
H13 H 0.7006 -0.5699 -0.2765 0.075 Uiso 1 1 calc R
C14 C 0.7726(3) -0.6194(3) -0.1617(3) 0.0586(10) Uani 1 1 d .
C15 C 0.8122(3) -0.5933(3) -0.0858(3) 0.0623(11) Uani 1 1 d .
H15 H 0.8404 -0.6402 -0.0422 0.075 Uiso 1 1 calc R
C16 C 0.8098(3) -0.4966(3) -0.0746(3) 0.0560(10) Uani 1 1 d .
H16 H 0.8366 -0.4786 -0.0229 0.067 Uiso 1 1 calc R
C17 C 0.8070(3) -0.1266(3) -0.0163(2) 0.0443(9) Uani 1 1 d .
C18 C 0.8023(3) -0.0293(3) -0.0041(3) 0.0604(11) Uani 1 1 d .
H18 H 0.7535 0.0198 -0.0333 0.072 Uiso 1 1 calc R
C19 C 0.8690(4) -0.0044(4) 0.0509(3) 0.0781(13) Uani 1 1 d .
H19 H 0.8652 0.0613 0.0585 0.094 Uiso 1 1 calc R
C20 C 0.9411(4) -0.0758(4) 0.0945(3) 0.0761(13) Uani 1 1 d .
H20 H 0.9861 -0.0588 0.1318 0.091 Uiso 1 1 calc R
C21 C 0.9464(3) -0.1716(4) 0.0828(3) 0.0686(12) Uani 1 1 d .
H21 H 0.9952 -0.2203 0.1123 0.082 Uiso 1 1 calc R
C22 C 0.8799(3) -0.1978(3) 0.0275(3) 0.0568(10) Uani 1 1 d .
H22 H 0.8847 -0.2637 0.0199 0.068 Uiso 1 1 calc R
C23 C 0.5760(3) 0.0027(2) -0.2422(3) 0.0466(9) Uani 1 1 d .
C24 C 0.5838(4) -0.0306(3) -0.3310(3) 0.0697(12) Uani 1 1 d .
H24 H 0.5752 -0.0916 -0.3427 0.084 Uiso 1 1 calc R
C25 C 0.6044(4) 0.0271(4) -0.4038(3) 0.0817(14) Uani 1 1 d .
H25 H 0.6107 0.0036 -0.4641 0.098 Uiso 1 1 calc R
C26 C 0.6158(3) 0.1173(3) -0.3889(3) 0.0686(12) Uani 1 1 d .
C27 C 0.6064(3) 0.1502(3) -0.2994(4) 0.0711(13) Uani 1 1 d .
H27 H 0.6138 0.2117 -0.2881 0.085 Uiso 1 1 calc R
C28 C 0.5862(3) 0.0942(3) -0.2258(3) 0.0603(11) Uani 1 1 d .
H28 H 0.5796 0.1181 -0.1655 0.072 Uiso 1 1 calc R
C29 C 0.6410(4) 0.1783(4) -0.4684(4) 0.1068(19) Uani 1 1 d .
H29B H 0.6189 0.2464 -0.4505 0.160 Uiso 1 1 calc R
H29A H 0.6054 0.1695 -0.5208 0.160 Uiso 1 1 calc R
H29C H 0.7147 0.1577 -0.4846 0.160 Uiso 1 1 calc R
C30 C 0.9054(3) 0.2683(3) 0.1528(3) 0.0685(12) Uani 1 1 d .
H30B H 0.9364 0.2198 0.1054 0.103 Uiso 1 1 calc R
H30A H 0.8316 0.2787 0.1594 0.103 Uiso 1 1 calc R
H30C H 0.9342 0.2458 0.2103 0.103 Uiso 1 1 calc R
C31 C 0.8879(3) 0.4361(3) 0.1881(2) 0.0477(9) Uani 1 1 d .
C32 C 0.9114(3) 0.5215(3) 0.1622(2) 0.0564(10) Uani 1 1 d .
H32 H 0.9524 0.5222 0.1075 0.068 Uiso 1 1 calc R
C33 C 0.8754(3) 0.6054(3) 0.2159(2) 0.0514(10) Uani 1 1 d .
H33 H 0.8917 0.6624 0.1978 0.062 Uiso 1 1 calc R
C34 C 0.8148(3) 0.6037(3) 0.2971(2) 0.0434(9) Uani 1 1 d .
C35 C 0.7944(3) 0.5167(2) 0.3243(2) 0.0402(8) Uani 1 1 d .
C36 C 0.8300(3) 0.4323(3) 0.2711(2) 0.0447(9) Uani 1 1 d .
H36 H 0.8159 0.3746 0.2902 0.054 Uiso 1 1 calc R
C37 C 0.7362(3) 0.5307(2) 0.4205(2) 0.0396(8) Uani 1 1 d .
C38 C 0.7249(3) 0.6396(2) 0.4376(2) 0.0435(8) Uani 1 1 d .
C39 C 0.7681(3) 0.6802(2) 0.3687(2) 0.0421(8) Uani 1 1 d .
C40 C 0.7698(3) 0.7833(3) 0.3583(2) 0.0455(9) Uani 1 1 d .
C41 C 0.7306(3) 0.8373(3) 0.2814(3) 0.0648(11) Uani 1 1 d .
H41 H 0.7000 0.8092 0.2386 0.078 Uiso 1 1 calc R
C42 C 0.7365(3) 0.9311(3) 0.2678(3) 0.0670(12) Uani 1 1 d .
H42 H 0.7088 0.9669 0.2169 0.080 Uiso 1 1 calc R
C43 C 0.7832(3) 0.9716(3) 0.3295(3) 0.0608(11) Uani 1 1 d .
C44 C 0.8206(3) 0.9214(3) 0.4064(3) 0.0622(11) Uani 1 1 d .
H44 H 0.8508 0.9502 0.4490 0.075 Uiso 1 1 calc R
C45 C 0.8131(3) 0.8279(3) 0.4205(3) 0.0542(10) Uani 1 1 d .
H45 H 0.8380 0.7941 0.4733 0.065 Uiso 1 1 calc R
C46 C 0.8031(3) 0.4611(3) 0.4886(2) 0.0414(8) Uani 1 1 d .
C47 C 0.8725(3) 0.4908(3) 0.5364(3) 0.0548(10) Uani 1 1 d .
H47 H 0.8769 0.5545 0.5294 0.066 Uiso 1 1 calc R
C48 C 0.9357(3) 0.4271(4) 0.5946(3) 0.0670(12) Uani 1 1 d .
H48 H 0.9819 0.4483 0.6268 0.080 Uiso 1 1 calc R
C49 C 0.9309(3) 0.3332(4) 0.6054(3) 0.0745(13) Uani 1 1 d .
H49 H 0.9737 0.2904 0.6447 0.089 Uiso 1 1 calc R
C50 C 0.8625(4) 0.3026(3) 0.5577(3) 0.0764(14) Uani 1 1 d .
H50 H 0.8589 0.2386 0.5647 0.092 Uiso 1 1 calc R
C51 C 0.7986(3) 0.3662(3) 0.4991(3) 0.0579(10) Uani 1 1 d .
H51 H 0.7527 0.3446 0.4668 0.070 Uiso 1 1 calc R
C52 C 0.5731(3) 0.4609(2) 0.2643(2) 0.0447(9) Uani 1 1 d .
C53 C 0.5832(4) 0.4862(3) 0.1732(3) 0.0690(12) Uani 1 1 d .
H53 H 0.5778 0.5509 0.1571 0.083 Uiso 1 1 calc R
C54 C 0.6013(4) 0.4147(4) 0.1057(3) 0.0821(14) Uani 1 1 d .
H54 H 0.6081 0.4321 0.0439 0.099 Uiso 1 1 calc R
C55 C 0.6095(3) 0.3196(4) 0.1270(4) 0.0723(13) Uani 1 1 d .
C56 C 0.5976(3) 0.2957(3) 0.2182(4) 0.0712(12) Uani 1 1 d .
H56 H 0.6016 0.2311 0.2339 0.085 Uiso 1 1 calc R
C57 C 0.5800(3) 0.3651(3) 0.2873(3) 0.0596(11) Uani 1 1 d .
H57 H 0.5728 0.3475 0.3490 0.072 Uiso 1 1 calc R
C58 C 0.6336(4) 0.2412(4) 0.0521(4) 0.114(2) Uani 1 1 d .
H58B H 0.6193 0.1833 0.0770 0.171 Uiso 1 1 calc R
H58C H 0.7056 0.2255 0.0300 0.171 Uiso 1 1 calc R
H58A H 0.5911 0.2653 0.0019 0.171 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.06299(19) 0.06963(18) 0.05348(17) 0.00050(13) 0.01109(13) -0.02356(15)
I2 0.05864(19) 0.06547(17) 0.05404(17) -0.01182(13) 0.01011(13) -0.01308(14)
Cl1 0.1258(12) 0.0658(7) 0.0940(9) -0.0119(6) -0.0149(8) -0.0403(7)
Cl2 0.1350(13) 0.0614(7) 0.1034(10) 0.0154(7) -0.0003(9) -0.0372(8)
S1 0.0412(6) 0.0589(6) 0.0549(6) -0.0057(5) -0.0030(5) -0.0136(5)
S2 0.0356(5) 0.0533(5) 0.0530(6) 0.0039(5) -0.0065(4) -0.0090(4)
O1 0.072(2) 0.086(2) 0.0511(17) 0.0101(16) 0.0005(15) -0.0288(17)
O2 0.0606(18) 0.0610(16) 0.0744(19) -0.0042(14) -0.0130(14) -0.0283(14)
O3 0.0396(16) 0.092(2) 0.0638(18) -0.0065(16) 0.0010(13) -0.0071(15)
O4 0.0577(18) 0.0789(19) 0.0491(16) -0.0112(15) 0.0062(13) -0.0113(15)
O5 0.0548(17) 0.0476(14) 0.0782(19) 0.0130(13) -0.0169(14) -0.0098(13)
O6 0.0323(15) 0.0894(19) 0.0640(18) 0.0009(15) -0.0013(13) -0.0112(14)
N1 0.0424(18) 0.0532(17) 0.0476(18) -0.0099(14) -0.0033(14) -0.0065(15)
N2 0.0355(17) 0.0585(17) 0.0415(17) 0.0070(14) -0.0038(13) -0.0174(14)
C1 0.078(3) 0.089(3) 0.080(3) 0.018(3) 0.004(3) -0.032(3)
C2 0.049(2) 0.063(2) 0.042(2) -0.0097(19) -0.0066(18) -0.010(2)
C3 0.049(2) 0.082(3) 0.033(2) -0.004(2) 0.0011(17) -0.012(2)
C4 0.044(2) 0.071(3) 0.041(2) 0.009(2) -0.0084(18) -0.013(2)
C5 0.045(2) 0.055(2) 0.047(2) 0.0018(19) -0.0061(18) -0.0101(19)
C6 0.035(2) 0.054(2) 0.038(2) -0.0004(17) -0.0055(16) -0.0067(17)
C7 0.038(2) 0.057(2) 0.038(2) -0.0029(17) -0.0061(16) -0.0096(18)
C8 0.040(2) 0.049(2) 0.042(2) -0.0012(17) -0.0076(17) -0.0092(17)
C9 0.042(2) 0.054(2) 0.044(2) -0.0015(18) -0.0018(17) -0.0143(18)
C10 0.042(2) 0.048(2) 0.041(2) -0.0035(16) 0.0023(16) -0.0115(18)
C11 0.045(2) 0.057(2) 0.040(2) -0.0060(18) -0.0013(17) -0.0134(19)
C12 0.066(3) 0.067(3) 0.054(3) 0.007(2) -0.024(2) -0.018(2)
C13 0.066(3) 0.079(3) 0.050(2) -0.007(2) -0.018(2) -0.029(2)
C14 0.063(3) 0.058(2) 0.058(3) -0.008(2) -0.006(2) -0.022(2)
C15 0.075(3) 0.056(2) 0.054(3) 0.000(2) -0.017(2) -0.013(2)
C16 0.062(3) 0.061(2) 0.044(2) -0.0029(19) -0.0159(19) -0.013(2)
C17 0.037(2) 0.058(2) 0.037(2) -0.0026(17) 0.0018(16) -0.0140(18)
C18 0.056(3) 0.061(3) 0.063(3) -0.002(2) -0.007(2) -0.016(2)
C19 0.075(3) 0.080(3) 0.091(4) -0.012(3) -0.009(3) -0.039(3)
C20 0.061(3) 0.110(4) 0.068(3) -0.007(3) -0.013(2) -0.039(3)
C21 0.050(3) 0.094(3) 0.060(3) 0.005(3) -0.007(2) -0.018(2)
C22 0.048(2) 0.068(2) 0.053(2) -0.002(2) -0.005(2) -0.014(2)
C23 0.039(2) 0.046(2) 0.051(2) -0.0058(17) -0.0046(17) -0.0061(17)
C24 0.090(4) 0.065(3) 0.058(3) -0.013(2) -0.005(2) -0.029(2)
C25 0.096(4) 0.096(4) 0.052(3) -0.003(3) -0.003(3) -0.027(3)
C26 0.051(3) 0.064(3) 0.084(4) 0.014(3) -0.009(2) -0.006(2)
C27 0.064(3) 0.045(2) 0.100(4) 0.006(3) -0.020(3) -0.006(2)
C28 0.065(3) 0.046(2) 0.065(3) -0.010(2) -0.010(2) -0.006(2)
C29 0.083(4) 0.108(4) 0.120(5) 0.052(4) -0.003(3) -0.016(3)
C30 0.059(3) 0.076(3) 0.065(3) -0.021(2) -0.001(2) -0.013(2)
C31 0.035(2) 0.064(2) 0.040(2) -0.0037(19) -0.0062(17) -0.0079(19)
C32 0.047(2) 0.088(3) 0.032(2) 0.000(2) 0.0052(17) -0.019(2)
C33 0.050(2) 0.066(2) 0.041(2) 0.010(2) -0.0069(18) -0.022(2)
C34 0.037(2) 0.058(2) 0.036(2) 0.0063(17) -0.0105(16) -0.0134(18)
C35 0.0306(19) 0.054(2) 0.0354(19) 0.0044(17) -0.0052(15) -0.0104(17)
C36 0.036(2) 0.051(2) 0.047(2) -0.0001(18) -0.0030(17) -0.0128(17)
C37 0.0334(19) 0.050(2) 0.0356(19) 0.0016(16) -0.0015(15) -0.0124(16)
C38 0.035(2) 0.052(2) 0.041(2) -0.0022(17) -0.0013(16) -0.0088(17)
C39 0.040(2) 0.053(2) 0.036(2) 0.0011(17) -0.0089(16) -0.0155(17)
C40 0.044(2) 0.052(2) 0.040(2) 0.0046(17) -0.0068(17) -0.0137(18)
C41 0.073(3) 0.076(3) 0.051(2) 0.011(2) -0.021(2) -0.026(2)
C42 0.073(3) 0.068(3) 0.056(3) 0.019(2) -0.013(2) -0.014(2)
C43 0.068(3) 0.047(2) 0.065(3) 0.007(2) -0.002(2) -0.015(2)
C44 0.072(3) 0.058(2) 0.062(3) -0.002(2) -0.013(2) -0.027(2)
C45 0.058(3) 0.057(2) 0.049(2) 0.0111(19) -0.017(2) -0.018(2)
C46 0.032(2) 0.055(2) 0.0345(19) -0.0002(16) 0.0029(15) -0.0098(17)
C47 0.044(2) 0.070(2) 0.049(2) 0.005(2) -0.0057(19) -0.015(2)
C48 0.047(3) 0.096(3) 0.054(3) 0.002(2) -0.013(2) -0.014(2)
C49 0.046(3) 0.092(4) 0.068(3) 0.020(3) -0.008(2) 0.006(3)
C50 0.068(3) 0.063(3) 0.090(4) 0.023(3) -0.010(3) -0.007(3)
C51 0.052(3) 0.059(2) 0.063(3) 0.009(2) -0.012(2) -0.015(2)
C52 0.037(2) 0.049(2) 0.051(2) 0.0069(18) -0.0076(17) -0.0170(17)
C53 0.091(4) 0.061(3) 0.055(3) 0.015(2) -0.004(2) -0.024(2)
C54 0.095(4) 0.105(4) 0.047(3) -0.005(3) 0.004(2) -0.034(3)
C55 0.047(3) 0.087(3) 0.087(4) -0.027(3) -0.003(2) -0.024(2)
C56 0.068(3) 0.061(3) 0.095(4) -0.003(3) -0.012(3) -0.032(2)
C57 0.060(3) 0.063(3) 0.063(3) 0.011(2) -0.010(2) -0.028(2)
C58 0.085(4) 0.143(5) 0.124(5) -0.072(4) 0.010(4) -0.050(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 119.07(17)
O2 S1 N1 111.06(16)
O3 S1 N1 104.70(16)
O2 S1 C23 107.51(17)
O3 S1 C23 107.88(17)
N1 S1 C23 105.87(17)
O5 S2 O6 119.29(16)
O5 S2 N2 110.71(16)
O6 S2 N2 104.62(15)
O5 S2 C52 107.67(16)
O6 S2 C52 107.60(17)
N2 S2 C52 106.21(15)
C4 O1 C1 117.9(3)
C31 O4 C30 117.7(3)
C10 N1 S1 124.7(2)
C10 N1 H1 117.7
S1 N1 H1 117.7
C37 N2 S2 125.2(2)
C37 N2 H2A 117.4
S2 N2 H2A 117.4
O1 C1 H1C 109.5
O1 C1 H1B 109.5
H1C C1 H1B 109.5
O1 C1 H1A 109.5
H1C C1 H1A 109.5
H1B C1 H1A 109.5
C3 C2 C7 119.2(4)
C3 C2 H2 120.4
C7 C2 H2 120.4
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
O1 C4 C5 124.7(4)
O1 C4 C3 115.3(3)
C5 C4 C3 120.0(4)
C6 C5 C4 118.3(3)
C6 C5 H5 120.8
C4 C5 H5 120.8
C5 C6 C7 122.3(3)
C5 C6 C10 128.6(3)
C7 C6 C10 109.0(3)
C6 C7 C2 119.2(3)
C6 C7 C8 110.0(3)
C2 C7 C8 130.7(3)
C9 C8 C11 129.1(3)
C9 C8 C7 107.5(3)
C11 C8 C7 123.4(3)
C8 C9 C10 113.3(3)
C8 C9 I1 126.9(3)
C10 C9 I1 119.7(2)
N1 C10 C9 112.9(3)
N1 C10 C17 108.4(3)
C9 C10 C17 113.0(3)
N1 C10 C6 113.6(3)
C9 C10 C6 100.1(3)
C17 C10 C6 108.6(3)
C16 C11 C12 117.2(3)
C16 C11 C8 122.6(3)
C12 C11 C8 120.3(3)
C13 C12 C11 121.8(4)
C13 C12 H12 119.1
C11 C12 H12 119.1
C14 C13 C12 118.8(4)
C14 C13 H13 120.6
C12 C13 H13 120.6
C15 C14 C13 121.5(4)
C15 C14 Cl1 119.3(3)
C13 C14 Cl1 119.2(3)
C14 C15 C16 119.2(4)
C14 C15 H15 120.4
C16 C15 H15 120.4
C15 C16 C11 121.5(4)
C15 C16 H16 119.3
C11 C16 H16 119.3
C22 C17 C18 118.6(4)
C22 C17 C10 120.3(3)
C18 C17 C10 121.0(3)
C19 C18 C17 120.5(4)
C19 C18 H18 119.7
C17 C18 H18 119.7
C20 C19 C18 120.5(4)
C20 C19 H19 119.7
C18 C19 H19 119.7
C21 C20 C19 119.3(4)
C21 C20 H20 120.3
C19 C20 H20 120.3
C20 C21 C22 120.8(4)
C20 C21 H21 119.6
C22 C21 H21 119.6
C17 C22 C21 120.3(4)
C17 C22 H22 119.9
C21 C22 H22 119.9
C24 C23 C28 119.7(4)
C24 C23 S1 119.6(3)
C28 C23 S1 120.7(3)
C23 C24 C25 119.7(4)
C23 C24 H24 120.1
C25 C24 H24 120.1
C26 C25 C24 121.4(4)
C26 C25 H25 119.3
C24 C25 H25 119.3
C25 C26 C27 118.2(4)
C25 C26 C29 120.9(5)
C27 C26 C29 120.9(5)
C26 C27 C28 121.6(4)
C26 C27 H27 119.2
C28 C27 H27 119.2
C23 C28 C27 119.4(4)
C23 C28 H28 120.3
C27 C28 H28 120.3
C26 C29 H29B 109.5
C26 C29 H29A 109.5
H29B C29 H29A 109.5
C26 C29 H29C 109.5
H29B C29 H29C 109.5
H29A C29 H29C 109.5
O4 C30 H30B 109.5
O4 C30 H30A 109.5
H30B C30 H30A 109.5
O4 C30 H30C 109.5
H30B C30 H30C 109.5
H30A C30 H30C 109.5
O4 C31 C32 115.9(3)
O4 C31 C36 123.8(3)
C32 C31 C36 120.3(3)
C33 C32 C31 121.2(3)
C33 C32 H32 119.4
C31 C32 H32 119.4
C32 C33 C34 119.0(3)
C32 C33 H33 120.5
C34 C33 H33 120.5
C33 C34 C35 119.5(3)
C33 C34 C39 131.1(3)
C35 C34 C39 109.4(3)
C36 C35 C34 122.0(3)
C36 C35 C37 128.5(3)
C34 C35 C37 109.4(3)
C35 C36 C31 118.0(3)
C35 C36 H36 121.0
C31 C36 H36 121.0
N2 C37 C35 113.6(3)
N2 C37 C38 112.6(3)
C35 C37 C38 100.0(3)
N2 C37 C46 107.8(3)
C35 C37 C46 109.3(3)
C38 C37 C46 113.5(3)
C39 C38 C37 113.2(3)
C39 C38 I2 127.0(3)
C37 C38 I2 119.6(2)
C38 C39 C40 129.0(3)
C38 C39 C34 107.9(3)
C40 C39 C34 123.1(3)
C45 C40 C41 117.6(3)
C45 C40 C39 122.2(3)
C41 C40 C39 120.1(3)
C42 C41 C40 121.1(4)
C42 C41 H41 119.5
C40 C41 H41 119.5
C43 C42 C41 119.5(4)
C43 C42 H42 120.2
C41 C42 H42 120.2
C42 C43 C44 120.8(4)
C42 C43 Cl2 119.7(3)
C44 C43 Cl2 119.5(4)
C43 C44 C45 119.5(4)
C43 C44 H44 120.3
C45 C44 H44 120.3
C40 C45 C44 121.4(4)
C40 C45 H45 119.3
C44 C45 H45 119.3
C47 C46 C51 118.8(3)
C47 C46 C37 120.6(3)
C51 C46 C37 120.5(3)
C46 C47 C48 120.7(4)
C46 C47 H47 119.7
C48 C47 H47 119.7
C49 C48 C47 120.6(4)
C49 C48 H48 119.7
C47 C48 H48 119.7
C48 C49 C50 119.3(4)
C48 C49 H49 120.3
C50 C49 H49 120.3
C49 C50 C51 120.6(4)
C49 C50 H50 119.7
C51 C50 H50 119.7
C46 C51 C50 120.1(4)
C46 C51 H51 119.9
C50 C51 H51 119.9
C53 C52 C57 119.8(4)
C53 C52 S2 120.0(3)
C57 C52 S2 120.2(3)
C52 C53 C54 119.3(4)
C52 C53 H53 120.3
C54 C53 H53 120.3
C55 C54 C53 121.8(4)
C55 C54 H54 119.1
C53 C54 H54 119.1
C54 C55 C56 118.2(4)
C54 C55 C58 121.1(5)
C56 C55 C58 120.7(5)
C55 C56 C57 121.4(4)
C55 C56 H56 119.3
C57 C56 H56 119.3
C56 C57 C52 119.4(4)
C56 C57 H57 120.3
C52 C57 H57 120.3
C55 C58 H58B 109.5
C55 C58 H58C 109.5
H58B C58 H58C 109.5
C55 C58 H58A 109.5
H58B C58 H58A 109.5
H58C C58 H58A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C9 2.071(3)
I2 C38 2.075(3)
Cl1 C14 1.747(4)
Cl2 C43 1.747(4)
S1 O2 1.422(3)
S1 O3 1.440(3)
S1 N1 1.621(3)
S1 C23 1.758(4)
S2 O5 1.420(2)
S2 O6 1.435(3)
S2 N2 1.614(3)
S2 C52 1.756(4)
O1 C4 1.369(4)
O1 C1 1.410(5)
O4 C31 1.370(4)
O4 C30 1.422(5)
N1 C10 1.466(4)
N1 H1 0.8600
N2 C37 1.473(4)
N2 H2A 0.8600
C1 H1C 0.9600
C1 H1B 0.9600
C1 H1A 0.9600
C2 C3 1.377(5)
C2 C7 1.388(5)
C2 H2 0.9300
C3 C4 1.392(5)
C3 H3 0.9300
C4 C5 1.391(5)
C5 C6 1.371(5)
C5 H5 0.9300
C6 C7 1.386(5)
C6 C10 1.540(5)
C7 C8 1.479(5)
C8 C9 1.333(5)
C8 C11 1.470(5)
C9 C10 1.531(5)
C10 C17 1.532(5)
C11 C16 1.390(5)
C11 C12 1.392(5)
C12 C13 1.376(5)
C12 H12 0.9300
C13 C14 1.369(5)
C13 H13 0.9300
C14 C15 1.365(5)
C15 C16 1.380(5)
C15 H15 0.9300
C16 H16 0.9300
C17 C22 1.375(5)
C17 C18 1.382(5)
C18 C19 1.376(6)
C18 H18 0.9300
C19 C20 1.369(6)
C19 H19 0.9300
C20 C21 1.358(6)
C20 H20 0.9300
C21 C22 1.383(6)
C21 H21 0.9300
C22 H22 0.9300
C23 C24 1.366(5)
C23 C28 1.377(5)
C24 C25 1.387(6)
C24 H24 0.9300
C25 C26 1.361(6)
C25 H25 0.9300
C26 C27 1.370(6)
C26 C29 1.509(6)
C27 C28 1.379(6)
C27 H27 0.9300
C28 H28 0.9300
C29 H29B 0.9600
C29 H29A 0.9600
C29 H29C 0.9600
C30 H30B 0.9600
C30 H30A 0.9600
C30 H30C 0.9600
C31 C32 1.384(5)
C31 C36 1.390(5)
C32 C33 1.376(5)
C32 H32 0.9300
C33 C34 1.382(5)
C33 H33 0.9300
C34 C35 1.391(5)
C34 C39 1.479(5)
C35 C36 1.376(5)
C35 C37 1.529(4)
C36 H36 0.9300
C37 C38 1.535(5)
C37 C46 1.536(5)
C38 C39 1.324(5)
C39 C40 1.479(5)
C40 C45 1.374(5)
C40 C41 1.393(5)
C41 C42 1.372(5)
C41 H41 0.9300
C42 C43 1.363(6)
C42 H42 0.9300
C43 C44 1.364(5)
C44 C45 1.376(5)
C44 H44 0.9300
C45 H45 0.9300
C46 C47 1.376(5)
C46 C51 1.376(5)
C47 C48 1.377(5)
C47 H47 0.9300
C48 C49 1.362(6)
C48 H48 0.9300
C49 C50 1.370(6)
C49 H49 0.9300
C50 C51 1.385(5)
C50 H50 0.9300
C51 H51 0.9300
C52 C53 1.370(5)
C52 C57 1.376(5)
C53 C54 1.379(6)
C53 H53 0.9300
C54 C55 1.357(6)
C54 H54 0.9300
C55 C56 1.369(6)
C55 C58 1.515(6)
C56 C57 1.375(6)
C56 H56 0.9300
C57 H57 0.9300
C58 H58B 0.9600
C58 H58C 0.9600
C58 H58A 0.9600
|
1501960.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501960.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501960
loop_
_publ_author_name
'Zhu, Yuanxun'
'Yin, Guangwei'
'Hong, Deng'
'Lu, Ping'
'Wang, Yanguang'
_publ_section_title
;
Tandem reaction of propargylic alcohol, sulfonamide, and
N-iodosuccinimide: synthesis of N-(2-iodoinden-1-yl)arenesulfonamide.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1024
_journal_page_last 1027
_journal_paper_doi 10.1021/ol103074d
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C28 H22 I N O2 S'
_chemical_formula_sum 'C28 H22 I N O2 S'
_chemical_formula_weight 563.43
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 92.515(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 9.2913(4)
_cell_length_b 29.4694(15)
_cell_length_c 8.8308(4)
_cell_measurement_reflns_used 4819
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.2753
_cell_measurement_theta_min 3.1844
_cell_volume 2415.62(19)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0333
_diffrn_reflns_av_sigmaI/netI 0.0486
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 35
_diffrn_reflns_limit_k_min -35
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 13367
_diffrn_reflns_theta_full 25.35
_diffrn_reflns_theta_max 25.35
_diffrn_reflns_theta_min 3.19
_exptl_absorpt_coefficient_mu 1.438
_exptl_absorpt_correction_T_max 0.829
_exptl_absorpt_correction_T_min 0.785
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET)
(compiled Nov 17 2009,16:58:22)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.549
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1128
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.13
_refine_diff_density_max 0.882
_refine_diff_density_min -0.779
_refine_diff_density_rms 0.055
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.007
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 299
_refine_ls_number_reflns 4429
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.007
_refine_ls_R_factor_all 0.0631
_refine_ls_R_factor_gt 0.0340
_refine_ls_shift/su_max 0.013
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0679
_refine_ls_wR_factor_ref 0.0726
_reflns_number_gt 2896
_reflns_number_total 4429
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103074d_si_004.cif
_cod_data_source_block 100718_zyx173
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_Hall '-P 2ybc '
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1501960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.73659(2) 0.130378(9) 0.36089(3) 0.06305(11) Uani 1 1 d .
S1 S 0.81096(10) 0.08261(3) 0.84083(13) 0.0623(3) Uani 1 1 d .
O1 O 0.7127(3) 0.06035(8) 0.7372(4) 0.0868(10) Uani 1 1 d .
O2 O 0.7731(3) 0.08754(10) 0.9960(4) 0.0890(10) Uani 1 1 d .
N N 0.8618(3) 0.13381(9) 0.7883(3) 0.0488(7) Uani 1 1 d .
C1 C 0.4435(4) 0.13071(14) 0.8798(5) 0.0754(12) Uani 1 1 d .
H1 H 0.4330 0.1003 0.8534 0.090 Uiso 1 1 calc R
C2 C 0.3998(5) 0.14484(17) 1.0185(6) 0.0899(15) Uani 1 1 d .
H2 H 0.3628 0.1240 1.0857 0.108 Uiso 1 1 calc R
C3 C 0.4108(4) 0.18919(19) 1.0571(5) 0.0799(13) Uani 1 1 d .
H3 H 0.3808 0.1990 1.1507 0.096 Uiso 1 1 calc R
C4 C 0.4663(4) 0.21959(15) 0.9579(5) 0.0711(12) Uani 1 1 d .
H4 H 0.4714 0.2502 0.9833 0.085 Uiso 1 1 calc R
C5 C 0.5145(4) 0.20514(13) 0.8210(4) 0.0566(10) Uani 1 1 d .
H5 H 0.5556 0.2259 0.7563 0.068 Uiso 1 1 calc R
C6 C 0.5022(3) 0.16009(11) 0.7786(4) 0.0440(8) Uani 1 1 d .
C7 C 0.5419(3) 0.14412(10) 0.6264(4) 0.0397(8) Uani 1 1 d .
C8 C 0.4188(3) 0.12578(11) 0.5309(4) 0.0436(8) Uani 1 1 d .
C9 C 0.2938(3) 0.15117(13) 0.5075(4) 0.0581(10) Uani 1 1 d .
H9 H 0.2890 0.1804 0.5470 0.070 Uiso 1 1 calc R
C10 C 0.1762(4) 0.13336(16) 0.4257(5) 0.0695(12) Uani 1 1 d .
H10 H 0.0936 0.1507 0.4087 0.083 Uiso 1 1 calc R
C11 C 0.1822(4) 0.09023(18) 0.3703(5) 0.0744(13) Uani 1 1 d .
H11 H 0.1030 0.0782 0.3163 0.089 Uiso 1 1 calc R
C12 C 0.3038(4) 0.06453(14) 0.3933(5) 0.0695(12) Uani 1 1 d .
H12 H 0.3071 0.0352 0.3547 0.083 Uiso 1 1 calc R
C13 C 0.4220(3) 0.08218(12) 0.4743(4) 0.0544(10) Uani 1 1 d .
H13 H 0.5042 0.0645 0.4905 0.065 Uiso 1 1 calc R
C14 C 0.6774(3) 0.14601(10) 0.5825(4) 0.0410(8) Uani 1 1 d .
C15 C 0.8062(3) 0.15836(11) 0.6813(4) 0.0395(8) Uani 1 1 d .
C16 C 0.8798(3) 0.20241(10) 0.6558(4) 0.0402(8) Uani 1 1 d .
C17 C 0.8118(4) 0.23681(12) 0.5764(4) 0.0531(9) Uani 1 1 d .
H17 H 0.7212 0.2318 0.5305 0.064 Uiso 1 1 calc R
C18 C 0.8758(5) 0.27882(13) 0.5634(5) 0.0678(11) Uani 1 1 d .
H18 H 0.8277 0.3021 0.5113 0.081 Uiso 1 1 calc R
C19 C 1.0104(5) 0.28587(14) 0.6277(5) 0.0738(12) Uani 1 1 d .
H19 H 1.0546 0.3140 0.6186 0.089 Uiso 1 1 calc R
C20 C 1.0798(4) 0.25191(15) 0.7049(5) 0.0727(12) Uani 1 1 d .
H20 H 1.1713 0.2571 0.7483 0.087 Uiso 1 1 calc R
C21 C 1.0165(4) 0.20978(13) 0.7200(4) 0.0565(9) Uani 1 1 d .
H21 H 1.0651 0.1867 0.7727 0.068 Uiso 1 1 calc R
C22 C 0.9782(4) 0.05507(11) 0.8344(4) 0.0462(8) Uani 1 1 d .
C23 C 1.0136(4) 0.03217(14) 0.7083(5) 0.0697(11) Uani 1 1 d .
H23 H 0.9484 0.0305 0.6255 0.084 Uiso 1 1 calc R
C24 C 1.1460(5) 0.01138(14) 0.7026(5) 0.0724(12) Uani 1 1 d .
H24 H 1.1687 -0.0043 0.6154 0.087 Uiso 1 1 calc R
C25 C 1.2444(4) 0.01308(11) 0.8214(4) 0.0523(9) Uani 1 1 d .
C26 C 1.2049(4) 0.03555(13) 0.9488(5) 0.0649(11) Uani 1 1 d .
H26 H 1.2684 0.0366 1.0331 0.078 Uiso 1 1 calc R
C27 C 1.0735(4) 0.05648(13) 0.9544(4) 0.0658(11) Uani 1 1 d .
H27 H 1.0497 0.0718 1.0419 0.079 Uiso 1 1 calc R
C28 C 1.3898(4) -0.00831(13) 0.8115(5) 0.0782(13) Uani 1 1 d .
H28B H 1.4012 -0.0316 0.8870 0.117 Uiso 1 1 calc R
H28C H 1.4630 0.0143 0.8285 0.117 Uiso 1 1 calc R
H28A H 1.3985 -0.0214 0.7127 0.117 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04409(14) 0.0925(2) 0.05336(17) -0.00938(16) 0.01118(10) -0.01239(13)
S1 0.0488(5) 0.0494(6) 0.0887(9) 0.0200(6) 0.0033(5) -0.0005(4)
O1 0.0589(16) 0.0505(16) 0.148(3) 0.0183(18) -0.0266(18) -0.0120(13)
O2 0.089(2) 0.091(2) 0.090(2) 0.0414(18) 0.0458(17) 0.0220(16)
N 0.0425(15) 0.0450(16) 0.0584(19) 0.0055(16) -0.0042(14) -0.0015(13)
C1 0.083(3) 0.061(2) 0.085(3) -0.006(3) 0.041(2) -0.012(2)
C2 0.105(4) 0.086(4) 0.082(4) 0.003(3) 0.048(3) -0.010(3)
C3 0.060(3) 0.110(4) 0.072(3) -0.023(3) 0.022(2) 0.001(3)
C4 0.058(2) 0.073(3) 0.083(3) -0.032(3) -0.001(2) -0.001(2)
C5 0.047(2) 0.060(3) 0.063(3) -0.005(2) 0.0029(19) -0.0077(18)
C6 0.0282(16) 0.049(2) 0.055(2) -0.0031(19) -0.0005(15) -0.0010(15)
C7 0.0355(17) 0.0333(18) 0.050(2) 0.0021(16) 0.0028(15) -0.0030(14)
C8 0.0315(16) 0.052(2) 0.047(2) -0.0025(18) 0.0034(14) -0.0058(16)
C9 0.041(2) 0.065(2) 0.068(3) -0.002(2) -0.0023(18) -0.0020(18)
C10 0.039(2) 0.100(3) 0.069(3) 0.005(3) -0.0048(19) 0.000(2)
C11 0.047(2) 0.117(4) 0.059(3) -0.013(3) 0.0006(19) -0.024(3)
C12 0.059(3) 0.079(3) 0.072(3) -0.022(2) 0.015(2) -0.024(2)
C13 0.0392(19) 0.057(2) 0.067(3) -0.011(2) 0.0071(18) -0.0038(17)
C14 0.0364(17) 0.0405(19) 0.046(2) -0.0005(16) 0.0026(15) 0.0010(14)
C15 0.0332(16) 0.0420(19) 0.043(2) -0.0028(17) 0.0056(14) 0.0044(15)
C16 0.0359(17) 0.0398(19) 0.045(2) 0.0027(17) 0.0058(15) -0.0028(15)
C17 0.049(2) 0.049(2) 0.062(2) 0.005(2) 0.0063(18) -0.0043(18)
C18 0.087(3) 0.052(3) 0.066(3) 0.011(2) 0.010(2) -0.004(2)
C19 0.096(3) 0.056(3) 0.070(3) 0.000(2) 0.012(3) -0.031(2)
C20 0.063(2) 0.079(3) 0.075(3) -0.002(3) 0.000(2) -0.038(2)
C21 0.0421(19) 0.061(2) 0.066(3) 0.005(2) 0.0003(18) -0.0102(18)
C22 0.051(2) 0.041(2) 0.047(2) 0.0062(18) 0.0012(18) -0.0036(16)
C23 0.067(3) 0.087(3) 0.053(3) -0.010(2) -0.020(2) 0.006(2)
C24 0.081(3) 0.080(3) 0.056(3) -0.017(2) 0.003(2) 0.006(2)
C25 0.054(2) 0.040(2) 0.063(3) 0.0016(19) 0.004(2) -0.0034(17)
C26 0.060(2) 0.078(3) 0.055(3) -0.011(2) -0.016(2) 0.009(2)
C27 0.069(3) 0.078(3) 0.050(3) -0.014(2) -0.004(2) 0.014(2)
C28 0.057(2) 0.064(3) 0.115(4) -0.008(3) 0.014(2) 0.006(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 118.86(19)
O1 S1 N 115.02(16)
O2 S1 N 105.08(17)
O1 S1 C22 108.02(17)
O2 S1 C22 109.37(17)
N S1 C22 98.54(14)
C15 N S1 127.7(2)
C2 C1 C6 122.0(4)
C2 C1 H1 119.0
C6 C1 H1 119.0
C3 C2 C1 119.7(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 119.8(4)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 120.4(4)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.6(4)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 117.4(4)
C1 C6 C7 120.7(3)
C5 C6 C7 121.9(3)
C14 C7 C6 121.6(3)
C14 C7 C8 124.1(3)
C6 C7 C8 114.3(2)
C13 C8 C9 118.6(3)
C13 C8 C7 120.9(3)
C9 C8 C7 120.3(3)
C10 C9 C8 120.5(4)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 119.7(4)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.6(4)
C10 C11 H11 119.7
C12 C11 H11 119.7
C11 C12 C13 120.0(4)
C11 C12 H12 120.0
C13 C12 H12 120.0
C8 C13 C12 120.5(3)
C8 C13 H13 119.8
C12 C13 H13 119.8
C7 C14 C15 125.6(3)
C7 C14 I1 123.3(2)
C15 C14 I1 111.2(2)
N C15 C16 115.5(3)
N C15 C14 125.5(3)
C16 C15 C14 119.0(3)
C17 C16 C21 119.1(3)
C17 C16 C15 121.2(3)
C21 C16 C15 119.6(3)
C16 C17 C18 121.0(3)
C16 C17 H17 119.5
C18 C17 H17 119.5
C19 C18 C17 119.4(4)
C19 C18 H18 120.3
C17 C18 H18 120.3
C20 C19 C18 120.1(4)
C20 C19 H19 119.9
C18 C19 H19 119.9
C19 C20 C21 121.1(4)
C19 C20 H20 119.5
C21 C20 H20 119.5
C20 C21 C16 119.2(4)
C20 C21 H21 120.4
C16 C21 H21 120.4
C27 C22 C23 119.1(3)
C27 C22 S1 120.7(3)
C23 C22 S1 120.2(3)
C22 C23 C24 120.1(4)
C22 C23 H23 120.0
C24 C23 H23 120.0
C25 C24 C23 121.8(4)
C25 C24 H24 119.1
C23 C24 H24 119.1
C24 C25 C26 117.1(3)
C24 C25 C28 121.2(4)
C26 C25 C28 121.8(4)
C25 C26 C27 121.3(4)
C25 C26 H26 119.4
C27 C26 H26 119.4
C22 C27 C26 120.8(4)
C22 C27 H27 119.6
C26 C27 H27 119.6
C25 C28 H28B 109.5
C25 C28 H28C 109.5
H28B C28 H28C 109.5
C25 C28 H28A 109.5
H28B C28 H28A 109.5
H28C C28 H28A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C14 2.106(3)
S1 O1 1.424(3)
S1 O2 1.437(3)
S1 N 1.653(3)
S1 C22 1.756(3)
N C15 1.281(4)
C1 C2 1.372(6)
C1 C6 1.374(5)
C1 H1 0.9300
C2 C3 1.353(6)
C2 H2 0.9300
C3 C4 1.369(6)
C3 H3 0.9300
C4 C5 1.375(5)
C4 H4 0.9300
C5 C6 1.382(5)
C5 H5 0.9300
C6 C7 1.486(5)
C7 C14 1.335(4)
C7 C8 1.492(4)
C8 C13 1.380(4)
C8 C9 1.390(4)
C9 C10 1.386(5)
C9 H9 0.9300
C10 C11 1.364(6)
C10 H10 0.9300
C11 C12 1.368(6)
C11 H11 0.9300
C12 C13 1.385(5)
C12 H12 0.9300
C13 H13 0.9300
C14 C15 1.494(4)
C15 C16 1.489(4)
C16 C17 1.371(4)
C16 C21 1.385(4)
C17 C18 1.380(5)
C17 H17 0.9300
C18 C19 1.367(5)
C18 H18 0.9300
C19 C20 1.357(6)
C19 H19 0.9300
C20 C21 1.382(5)
C20 H20 0.9300
C21 H21 0.9300
C22 C27 1.352(5)
C22 C23 1.355(5)
C23 C24 1.377(5)
C23 H23 0.9300
C24 C25 1.362(5)
C24 H24 0.9300
C25 C26 1.369(5)
C25 C28 1.497(5)
C26 C27 1.370(5)
C26 H26 0.9300
C27 H27 0.9300
C28 H28B 0.9600
C28 H28C 0.9600
C28 H28A 0.9600
|
1501961.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501961.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501961
loop_
_publ_author_name
'Donohoe, Timothy J.'
'Basutto, Jos\'e A'
'Bower, John F.'
'Rathi, Akshat'
_publ_section_title
;
Heteroaromatic synthesis via olefin cross-metathesis: entry to
polysubstituted pyridines.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1036
_journal_page_last 1039
_journal_paper_doi 10.1021/ol103088r
_journal_volume 13
_journal_year 2011
_chemical_compound_source Synthetic
_chemical_formula_moiety 'C20 H19 N1'
_chemical_formula_sum 'C20 H19 N'
_chemical_formula_weight 273.38
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 68.3797(10)
_cell_angle_beta 81.4469(9)
_cell_angle_gamma 62.3658(10)
_cell_formula_units_Z 2
_cell_length_a 9.3961(2)
_cell_length_b 9.4690(2)
_cell_length_c 10.2833(2)
_cell_measurement_reflns_used 2959
_cell_measurement_temperature 150
_cell_measurement_theta_max 27
_cell_measurement_theta_min 5
_cell_volume 753.26(3)
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection 'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature 150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_measurement_method \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.031
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 10759
_diffrn_reflns_theta_full 25.492
_diffrn_reflns_theta_max 27.411
_diffrn_reflns_theta_min 5.172
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.069
_exptl_absorpt_correction_T_max 0.97
_exptl_absorpt_correction_T_min 0.71
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.205
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 292
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.80
_exptl_crystal_size_min 0.40
_refine_diff_density_max 0.26
_refine_diff_density_min -0.28
_refine_ls_extinction_coef 190(40)
_refine_ls_extinction_method 'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref 0.9195
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 191
_refine_ls_number_reflns 2765
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0610
_refine_ls_R_factor_gt 0.0415
_refine_ls_shift/su_max 0.000187
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.30P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.1077
_refine_ls_wR_factor_gt 0.0980
_refine_ls_wR_factor_ref 0.1077
_reflns_limit_h_max 12
_reflns_limit_h_min -11
_reflns_limit_k_max 12
_reflns_limit_k_min -11
_reflns_limit_l_max 13
_reflns_limit_l_min 0
_reflns_number_gt 2108
_reflns_number_total 3377
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.41
_oxford_diffrn_Wilson_scale 0.55
_oxford_refine_ls_r_factor_ref 0.0610
_oxford_refine_ls_scale 1.416(11)
_oxford_reflns_number_all 2765
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file ol103088r_si_001.cif
_cod_data_source_block 42
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_formula_sum 'C20 H19 N1'
_cod_database_code 1501961
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
N1 N 0.48207(14) 0.23418(14) 0.80533(12) 0.0287 1.0000 Uani .
C2 C 0.59732(16) 0.21234(18) 0.70877(14) 0.0280 1.0000 Uani .
C3 C 0.63780(17) 0.09278(18) 0.64322(14) 0.0301 1.0000 Uani .
C4 C 0.54776(17) 0.00269(18) 0.67738(14) 0.0308 1.0000 Uani .
C5 C 0.42438(16) 0.02735(17) 0.77281(14) 0.0275 1.0000 Uani .
C6 C 0.39720(16) 0.14498(17) 0.83724(14) 0.0272 1.0000 Uani .
C7 C 0.27592(18) 0.17529(19) 0.94972(16) 0.0334 1.0000 Uani .
C8 C 0.33092(17) -0.07151(18) 0.80183(14) 0.0280 1.0000 Uani .
C9 C 0.40977(17) -0.24507(18) 0.82269(15) 0.0319 1.0000 Uani .
C10 C 0.32560(18) -0.33644(19) 0.83621(15) 0.0337 1.0000 Uani .
C11 C 0.15836(18) -0.25734(18) 0.82943(15) 0.0313 1.0000 Uani .
C12 C 0.07925(17) -0.08635(19) 0.81408(15) 0.0318 1.0000 Uani .
C13 C 0.16341(17) 0.00574(18) 0.79936(15) 0.0304 1.0000 Uani .
C14 C 0.0658(2) -0.3525(2) 0.83301(19) 0.0446 1.0000 Uani .
C15 C 0.77272(19) 0.0567(2) 0.54173(17) 0.0401 1.0000 Uani .
C16 C 0.68040(16) 0.32167(18) 0.68109(15) 0.0298 1.0000 Uani .
C17 C 0.73332(16) 0.33637(18) 0.79294(16) 0.0320 1.0000 Uani .
C18 C 0.80774(18) 0.4399(2) 0.76945(18) 0.0375 1.0000 Uani .
C19 C 0.82777(19) 0.5327(2) 0.63398(19) 0.0427 1.0000 Uani .
C20 C 0.77411(19) 0.5206(2) 0.52225(19) 0.0440 1.0000 Uani .
C21 C 0.70191(18) 0.4154(2) 0.54485(16) 0.0379 1.0000 Uani .
H41 H 0.5716 -0.0786 0.6321 0.0376 1.0000 Uiso R
H73 H 0.2709 0.0689 1.0110 0.0517 1.0000 Uiso R
H71 H 0.3042 0.2239 1.0064 0.0525 1.0000 Uiso R
H72 H 0.1684 0.2566 0.9059 0.0515 1.0000 Uiso R
H91 H 0.5275 -0.3029 0.8267 0.0376 1.0000 Uiso R
H101 H 0.3844 -0.4585 0.8496 0.0416 1.0000 Uiso R
H121 H -0.0383 -0.0312 0.8129 0.0405 1.0000 Uiso R
H131 H 0.1046 0.1257 0.7870 0.0371 1.0000 Uiso R
H141 H -0.0516 -0.2737 0.8198 0.0762 1.0000 Uiso R
H142 H 0.0855 -0.4446 0.9248 0.0760 1.0000 Uiso R
H143 H 0.1016 -0.4032 0.7590 0.0758 1.0000 Uiso R
H152 H 0.8130 -0.0599 0.5452 0.0616 1.0000 Uiso R
H153 H 0.8615 0.0747 0.5641 0.0617 1.0000 Uiso R
H151 H 0.7304 0.1306 0.4462 0.0614 1.0000 Uiso R
H171 H 0.7172 0.2716 0.8902 0.0387 1.0000 Uiso R
H181 H 0.8457 0.4487 0.8491 0.0476 1.0000 Uiso R
H191 H 0.8799 0.6102 0.6159 0.0523 1.0000 Uiso R
H201 H 0.7855 0.5894 0.4258 0.0519 1.0000 Uiso R
H211 H 0.6644 0.4057 0.4668 0.0447 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0259(6) 0.0298(6) 0.0271(6) -0.0077(5) 0.0012(5) -0.0114(5)
C2 0.0245(7) 0.0318(8) 0.0231(7) -0.0061(6) -0.0002(6) -0.0112(6)
C3 0.0266(7) 0.0374(8) 0.0230(7) -0.0086(6) 0.0008(6) -0.0128(6)
C4 0.0301(8) 0.0355(8) 0.0254(7) -0.0135(6) 0.0016(6) -0.0114(7)
C5 0.0252(7) 0.0284(7) 0.0246(7) -0.0072(6) -0.0005(6) -0.0096(6)
C6 0.0237(7) 0.0266(7) 0.0247(7) -0.0066(6) 0.0003(6) -0.0075(6)
C7 0.0309(8) 0.0346(8) 0.0328(8) -0.0141(7) 0.0063(6) -0.0128(7)
C8 0.0277(8) 0.0303(8) 0.0245(7) -0.0100(6) 0.0026(6) -0.0117(6)
C9 0.0267(7) 0.0321(8) 0.0317(8) -0.0117(6) 0.0031(6) -0.0089(6)
C10 0.0369(9) 0.0281(8) 0.0330(8) -0.0106(6) 0.0042(6) -0.0128(7)
C11 0.0361(9) 0.0354(8) 0.0268(8) -0.0127(6) 0.0071(6) -0.0196(7)
C12 0.0267(8) 0.0375(8) 0.0315(8) -0.0148(7) 0.0047(6) -0.0135(7)
C13 0.0285(8) 0.0289(8) 0.0311(8) -0.0113(6) 0.0019(6) -0.0101(6)
C14 0.0505(10) 0.0452(10) 0.0478(10) -0.0191(8) 0.0097(8) -0.0290(9)
C15 0.0384(9) 0.0534(10) 0.0321(8) -0.0196(8) 0.0103(7) -0.0221(8)
C16 0.0208(7) 0.0310(8) 0.0316(8) -0.0083(6) 0.0017(6) -0.0089(6)
C17 0.0254(7) 0.0327(8) 0.0341(8) -0.0120(7) 0.0025(6) -0.0099(6)
C18 0.0272(8) 0.0389(9) 0.0477(10) -0.0197(8) 0.0027(7) -0.0125(7)
C19 0.0323(9) 0.0386(9) 0.0587(11) -0.0156(8) 0.0060(8) -0.0191(7)
C20 0.0380(9) 0.0425(9) 0.0432(10) -0.0022(8) 0.0040(7) -0.0215(8)
C21 0.0329(8) 0.0452(9) 0.0325(9) -0.0063(7) 0.0003(7) -0.0200(7)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 120.06(12) yes
N1 C2 C3 122.24(13) yes
N1 C2 C16 114.64(12) yes
C3 C2 C16 123.09(12) yes
C2 C3 C4 116.57(13) yes
C2 C3 C15 123.88(13) yes
C4 C3 C15 119.54(13) yes
C3 C4 C5 122.22(13) yes
C3 C4 H41 118.2 no
C5 C4 H41 119.5 no
C4 C5 C6 116.97(13) yes
C4 C5 C8 119.09(12) yes
C6 C5 C8 123.93(12) yes
C5 C6 N1 121.83(13) yes
C5 C6 C7 122.69(13) yes
N1 C6 C7 115.44(12) yes
C6 C7 H73 111.3 no
C6 C7 H71 109.6 no
H73 C7 H71 109.8 no
C6 C7 H72 109.4 no
H73 C7 H72 108.0 no
H71 C7 H72 108.8 no
C5 C8 C9 120.30(12) yes
C5 C8 C13 121.95(13) yes
C9 C8 C13 117.59(13) yes
C8 C9 C10 121.51(13) yes
C8 C9 H91 119.2 no
C10 C9 H91 119.3 no
C9 C10 C11 120.56(14) yes
C9 C10 H101 119.8 no
C11 C10 H101 119.7 no
C10 C11 C12 118.18(13) yes
C10 C11 C14 120.97(14) yes
C12 C11 C14 120.81(14) yes
C11 C12 C13 121.29(13) yes
C11 C12 H121 118.5 no
C13 C12 H121 120.2 no
C8 C13 C12 120.80(13) yes
C8 C13 H131 119.9 no
C12 C13 H131 119.3 no
C11 C14 H141 109.8 no
C11 C14 H142 109.1 no
H141 C14 H142 109.4 no
C11 C14 H143 110.3 no
H141 C14 H143 109.6 no
H142 C14 H143 108.6 no
C3 C15 H152 109.0 no
C3 C15 H153 111.3 no
H152 C15 H153 110.2 no
C3 C15 H151 109.2 no
H152 C15 H151 107.0 no
H153 C15 H151 110.1 no
C2 C16 C17 119.70(13) yes
C2 C16 C21 121.61(13) yes
C17 C16 C21 118.65(14) yes
C16 C17 C18 120.59(14) yes
C16 C17 H171 119.3 no
C18 C17 H171 120.1 no
C17 C18 C19 120.24(15) yes
C17 C18 H181 120.1 no
C19 C18 H181 119.7 no
C18 C19 C20 119.68(15) yes
C18 C19 H191 120.8 no
C20 C19 H191 119.5 no
C19 C20 C21 120.42(15) yes
C19 C20 H201 119.7 no
C21 C20 H201 119.9 no
C16 C21 C20 120.41(15) yes
C16 C21 H211 118.7 no
C20 C21 H211 120.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.3510(18) yes
N1 C6 1.3416(18) yes
C2 C3 1.403(2) yes
C2 C16 1.493(2) yes
C3 C4 1.388(2) yes
C3 C15 1.510(2) yes
C4 C5 1.3932(19) yes
C4 H41 0.966 no
C5 C6 1.405(2) yes
C5 C8 1.488(2) yes
C6 C7 1.5060(19) yes
C7 H73 0.990 no
C7 H71 0.989 no
C7 H72 0.987 no
C8 C9 1.398(2) yes
C8 C13 1.394(2) yes
C9 C10 1.381(2) yes
C9 H91 0.980 no
C10 C11 1.392(2) yes
C10 H101 0.986 no
C11 C12 1.389(2) yes
C11 C14 1.504(2) yes
C12 C13 1.384(2) yes
C12 H121 0.979 no
C13 H131 0.972 no
C14 H141 0.999 no
C14 H142 0.990 no
C14 H143 0.983 no
C15 H152 0.975 no
C15 H153 0.998 no
C15 H151 0.982 no
C16 C17 1.394(2) yes
C16 C21 1.399(2) yes
C17 C18 1.386(2) yes
C17 H171 0.994 no
C18 C19 1.386(2) yes
C18 H181 0.985 no
C19 C20 1.382(3) yes
C19 H191 1.009 no
C20 C21 1.385(2) yes
C20 H201 0.988 no
C21 H211 0.972 no
|
1501962.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501962.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501962
loop_
_publ_author_name
'Donohoe, Timothy J.'
'Basutto, Jos\'e A'
'Bower, John F.'
'Rathi, Akshat'
_publ_section_title
;
Heteroaromatic synthesis via olefin cross-metathesis: entry to
polysubstituted pyridines.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1036
_journal_page_last 1039
_journal_paper_doi 10.1021/ol103088r
_journal_volume 13
_journal_year 2011
_chemical_compound_source Synthetic
_chemical_formula_moiety 'C22 H21 N1 O2'
_chemical_formula_sum 'C22 H21 N O2'
_chemical_formula_weight 331.41
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 90
_cell_angle_beta 73.7676(16)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 9.6999(3)
_cell_length_b 13.5546(5)
_cell_length_c 13.8504(6)
_cell_measurement_reflns_used 6880
_cell_measurement_temperature 150
_cell_measurement_theta_max 27
_cell_measurement_theta_min 5
_cell_volume 1748.43(11)
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection 'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature 150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_measurement_method \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.072
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 13742
_diffrn_reflns_theta_full 26.903
_diffrn_reflns_theta_max 27.452
_diffrn_reflns_theta_min 5.179
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.080
_exptl_absorpt_correction_T_max 0.98
_exptl_absorpt_correction_T_min 0.97
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.259
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 704
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.28
_refine_diff_density_max 0.39
_refine_diff_density_min -0.37
_refine_ls_extinction_coef 170(50)
_refine_ls_extinction_method 'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref 0.9462
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 227
_refine_ls_number_reflns 3349
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0870
_refine_ls_R_factor_gt 0.0512
_refine_ls_shift/su_max 0.000174
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.03P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.1232
_refine_ls_wR_factor_gt 0.1100
_refine_ls_wR_factor_ref 0.1230
_reflns_limit_h_max 12
_reflns_limit_h_min -11
_reflns_limit_k_max 17
_reflns_limit_k_min 0
_reflns_limit_l_max 17
_reflns_limit_l_min 0
_reflns_number_gt 2295
_reflns_number_total 3967
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.18
_oxford_diffrn_Wilson_scale 7.96
_oxford_refine_ls_r_factor_ref 0.0869
_oxford_refine_ls_scale 0.3681(7)
_oxford_reflns_number_all 3350
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file ol103088r_si_002.cif
_cod_data_source_block 43
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'P 1 21/c 1 '
_cod_original_formula_sum 'C22 H21 N1 O2'
_cod_database_code 1501962
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.20522(16) -0.06444(11) 0.35110(12) 0.0387 1.0000 Uani .
C2 C 0.1137(2) -0.00104(15) 0.36368(15) 0.0278 1.0000 Uani .
O3 O -0.02039(14) -0.01916(10) 0.35856(11) 0.0302 1.0000 Uani .
C4 C -0.0487(2) -0.12079(15) 0.33501(17) 0.0329 1.0000 Uani .
C5 C -0.1994(2) -0.12630(17) 0.32711(18) 0.0371 1.0000 Uani .
C6 C 0.1375(2) 0.10358(14) 0.38611(15) 0.0255 1.0000 Uani .
C7 C 0.0329(2) 0.17673(15) 0.39609(16) 0.0278 1.0000 Uani .
C8 C 0.0615(2) 0.27262(15) 0.41896(16) 0.0283 1.0000 Uani .
C9 C 0.1951(2) 0.29807(14) 0.43248(15) 0.0246 1.0000 Uani .
C10 C 0.2286(2) 0.40022(14) 0.45892(15) 0.0247 1.0000 Uani .
C11 C 0.3517(2) 0.44728(15) 0.40067(16) 0.0268 1.0000 Uani .
C12 C 0.3906(2) 0.54133(15) 0.42341(15) 0.0263 1.0000 Uani .
C13 C 0.5291(2) 0.58684(16) 0.36029(17) 0.0327 1.0000 Uani .
C14 C 0.2993(2) 0.58703(14) 0.50870(15) 0.0250 1.0000 Uani .
N15 N 0.18251(16) 0.54109(12) 0.56747(12) 0.0254 1.0000 Uani .
C16 C 0.1467(2) 0.45037(14) 0.54417(15) 0.0249 1.0000 Uani .
C17 C 0.0169(2) 0.40631(15) 0.61812(16) 0.0313 1.0000 Uani .
C18 C 0.3235(2) 0.68758(15) 0.54435(16) 0.0275 1.0000 Uani .
C19 C 0.3020(2) 0.70249(16) 0.64768(17) 0.0305 1.0000 Uani .
C20 C 0.3159(2) 0.79566(17) 0.68483(18) 0.0358 1.0000 Uani .
C21 C 0.3515(2) 0.87544(17) 0.6204(2) 0.0400 1.0000 Uani .
C22 C 0.3720(2) 0.86235(16) 0.5185(2) 0.0392 1.0000 Uani .
C23 C 0.3580(2) 0.76899(16) 0.48081(18) 0.0345 1.0000 Uani .
C24 C 0.2993(2) 0.22496(15) 0.42036(15) 0.0277 1.0000 Uani .
C25 C 0.2708(2) 0.12891(15) 0.39758(15) 0.0279 1.0000 Uani .
H41 H -0.0347 -0.1640 0.3897 0.0414 1.0000 Uiso R
H42 H 0.0203 -0.1404 0.2693 0.0411 1.0000 Uiso R
H52 H -0.2198 -0.1952 0.3125 0.0580 1.0000 Uiso R
H53 H -0.2663 -0.1065 0.3913 0.0580 1.0000 Uiso R
H51 H -0.2089 -0.0826 0.2731 0.0582 1.0000 Uiso R
H71 H -0.0610 0.1601 0.3872 0.0364 1.0000 Uiso R
H81 H -0.0105 0.3236 0.4259 0.0368 1.0000 Uiso R
H111 H 0.4119 0.4136 0.3420 0.0341 1.0000 Uiso R
H132 H 0.5754 0.6227 0.4036 0.0513 1.0000 Uiso R
H131 H 0.5938 0.5347 0.3243 0.0516 1.0000 Uiso R
H133 H 0.5080 0.6336 0.3116 0.0517 1.0000 Uiso R
H173 H -0.0041 0.4423 0.6821 0.0490 1.0000 Uiso R
H171 H 0.0322 0.3371 0.6306 0.0491 1.0000 Uiso R
H172 H -0.0662 0.4110 0.5918 0.0493 1.0000 Uiso R
H191 H 0.2781 0.6465 0.6924 0.0403 1.0000 Uiso R
H201 H 0.3004 0.8046 0.7560 0.0472 1.0000 Uiso R
H211 H 0.3619 0.9404 0.6457 0.0541 1.0000 Uiso R
H221 H 0.3948 0.9184 0.4739 0.0525 1.0000 Uiso R
H231 H 0.3712 0.7611 0.4085 0.0468 1.0000 Uiso R
H241 H 0.3938 0.2416 0.4279 0.0334 1.0000 Uiso R
H251 H 0.3427 0.0784 0.3898 0.0353 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0388(9) 0.0314(8) 0.0508(10) -0.0107(7) -0.0208(7) 0.0090(7)
C2 0.0294(11) 0.0296(11) 0.0254(11) -0.0029(9) -0.0092(9) 0.0030(9)
O3 0.0298(8) 0.0244(8) 0.0375(9) -0.0019(6) -0.0109(6) -0.0015(6)
C4 0.0384(12) 0.0222(11) 0.0392(13) -0.0043(10) -0.0127(10) -0.0014(9)
C5 0.0386(12) 0.0342(12) 0.0397(13) -0.0022(11) -0.0133(10) -0.0042(10)
C6 0.0277(10) 0.0245(11) 0.0242(10) -0.0011(9) -0.0072(8) 0.0004(9)
C7 0.0248(10) 0.0290(11) 0.0314(12) -0.0010(9) -0.0106(9) 0.0012(9)
C8 0.0237(10) 0.0261(11) 0.0359(12) -0.0015(9) -0.0098(9) 0.0039(9)
C9 0.0251(10) 0.0250(10) 0.0234(10) 0.0001(9) -0.0062(8) 0.0013(8)
C10 0.0231(10) 0.0242(10) 0.0294(11) 0.0005(9) -0.0118(8) 0.0031(8)
C11 0.0245(10) 0.0281(11) 0.0296(11) -0.0007(9) -0.0103(9) 0.0033(9)
C12 0.0234(10) 0.0279(11) 0.0286(11) 0.0048(9) -0.0092(9) 0.0011(8)
C13 0.0262(11) 0.0349(12) 0.0362(12) 0.0029(10) -0.0073(9) -0.0032(9)
C14 0.0237(10) 0.0239(10) 0.0300(11) 0.0029(9) -0.0118(9) -0.0005(8)
N15 0.0227(9) 0.0238(9) 0.0303(10) 0.0003(7) -0.0083(7) 0.0006(7)
C16 0.0224(10) 0.0225(10) 0.0319(12) 0.0014(9) -0.0111(9) 0.0013(8)
C17 0.0303(11) 0.0277(11) 0.0339(12) -0.0007(9) -0.0055(9) -0.0031(9)
C18 0.0202(10) 0.0263(11) 0.0378(13) -0.0001(9) -0.0112(9) 0.0008(8)
C19 0.0234(10) 0.0314(11) 0.0380(13) 0.0003(10) -0.0105(9) 0.0004(9)
C20 0.0275(11) 0.0391(13) 0.0436(14) -0.0121(11) -0.0144(10) 0.0026(10)
C21 0.0288(11) 0.0293(12) 0.0666(17) -0.0117(12) -0.0209(11) 0.0027(10)
C22 0.0336(12) 0.0255(12) 0.0613(17) 0.0073(11) -0.0183(11) -0.0014(10)
C23 0.0333(11) 0.0290(12) 0.0449(14) 0.0025(10) -0.0172(10) -0.0010(9)
C24 0.0212(10) 0.0309(12) 0.0308(12) -0.0024(9) -0.0071(8) 0.0003(9)
C25 0.0263(11) 0.0284(11) 0.0299(11) -0.0027(9) -0.0094(9) 0.0068(9)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C2 O3 122.88(19) yes
O1 C2 C6 123.88(18) yes
O3 C2 C6 113.24(17) yes
C2 O3 C4 115.42(15) yes
O3 C4 C5 108.16(17) yes
O3 C4 H41 108.1 no
C5 C4 H41 111.7 no
O3 C4 H42 109.5 no
C5 C4 H42 109.7 no
H41 C4 H42 109.6 no
C4 C5 H52 108.5 no
C4 C5 H53 109.4 no
H52 C5 H53 109.0 no
C4 C5 H51 109.1 no
H52 C5 H51 110.4 no
H53 C5 H51 110.3 no
C2 C6 C7 123.25(18) yes
C2 C6 C25 117.65(18) yes
C7 C6 C25 119.11(18) yes
C6 C7 C8 120.17(19) yes
C6 C7 H71 120.0 no
C8 C7 H71 119.9 no
C7 C8 C9 120.88(19) yes
C7 C8 H81 120.5 no
C9 C8 H81 118.6 no
C8 C9 C10 122.29(17) yes
C8 C9 C24 118.40(18) yes
C10 C9 C24 119.31(17) yes
C9 C10 C11 119.54(18) yes
C9 C10 C16 123.08(18) yes
C11 C10 C16 117.26(18) yes
C10 C11 C12 122.08(19) yes
C10 C11 H111 119.1 no
C12 C11 H111 118.8 no
C11 C12 C13 119.74(18) yes
C11 C12 C14 116.55(18) yes
C13 C12 C14 123.64(18) yes
C12 C13 H132 109.6 no
C12 C13 H131 109.7 no
H132 C13 H131 109.4 no
C12 C13 H133 109.6 no
H132 C13 H133 108.7 no
H131 C13 H133 109.9 no
C12 C14 N15 121.94(18) yes
C12 C14 C18 124.10(18) yes
N15 C14 C18 113.93(17) yes
C14 N15 C16 120.57(17) yes
C10 C16 N15 121.54(18) yes
C10 C16 C17 123.38(18) yes
N15 C16 C17 115.04(17) yes
C16 C17 H173 109.9 no
C16 C17 H171 111.3 no
H173 C17 H171 108.9 no
C16 C17 H172 109.9 no
H173 C17 H172 108.6 no
H171 C17 H172 108.2 no
C14 C18 C19 118.54(18) yes
C14 C18 C23 123.20(19) yes
C19 C18 C23 118.15(19) yes
C18 C19 C20 120.6(2) yes
C18 C19 H191 118.8 no
C20 C19 H191 120.6 no
C19 C20 C21 120.4(2) yes
C19 C20 H201 119.5 no
C21 C20 H201 120.1 no
C20 C21 C22 119.8(2) yes
C20 C21 H211 120.8 no
C22 C21 H211 119.3 no
C21 C22 C23 120.0(2) yes
C21 C22 H221 119.6 no
C23 C22 H221 120.4 no
C18 C23 C22 121.1(2) yes
C18 C23 H231 119.9 no
C22 C23 H231 119.0 no
C9 C24 C25 120.79(19) yes
C9 C24 H241 119.6 no
C25 C24 H241 119.6 no
C6 C25 C24 120.63(18) yes
C6 C25 H251 118.7 no
C24 C25 H251 120.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.212(2) yes
C2 O3 1.345(2) yes
C2 C6 1.483(3) yes
O3 C4 1.459(2) yes
C4 C5 1.498(3) yes
C4 H41 0.997 no
C4 H42 1.003 no
C5 H52 0.987 no
C5 H53 0.980 no
C5 H51 0.978 no
C6 C7 1.397(3) yes
C6 C25 1.390(3) yes
C7 C8 1.384(3) yes
C7 H71 0.978 no
C8 C9 1.403(3) yes
C8 H81 0.968 no
C9 C10 1.491(3) yes
C9 C24 1.392(3) yes
C10 C11 1.394(3) yes
C10 C16 1.401(3) yes
C11 C12 1.390(3) yes
C11 H111 0.973 no
C12 C13 1.515(3) yes
C12 C14 1.407(3) yes
C13 H132 0.974 no
C13 H131 0.983 no
C13 H133 0.988 no
C14 N15 1.349(2) yes
C14 C18 1.490(3) yes
N15 C16 1.342(2) yes
C16 C17 1.506(3) yes
C17 H173 0.982 no
C17 H171 0.973 no
C17 H172 0.975 no
C18 C19 1.402(3) yes
C18 C23 1.393(3) yes
C19 C20 1.385(3) yes
C19 H191 0.965 no
C20 C21 1.383(3) yes
C20 H201 0.963 no
C21 C22 1.381(3) yes
C21 H211 0.963 no
C22 C23 1.390(3) yes
C22 H221 0.965 no
C23 H231 0.979 no
C24 C25 1.386(3) yes
C24 H241 0.978 no
C25 H251 0.961 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 H81 N15 2_566 176 0.97 2.46 3.430(3) yes
C19 H191 O1 4_555 156 0.97 2.39 3.293(3) yes
|
1501963.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501963.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501963
loop_
_publ_author_name
'Brock, E. Anne'
'Davies, Stephen G.'
'Lee, James A.'
'Roberts, Paul M.'
'Thomson, James E.'
_publ_section_title
;
Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular
iodoamination with concomitant N-debenzylation.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1594
_journal_page_last 1597
_journal_paper_doi 10.1021/ol103090z
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C24 H35 I2 N1 O5'
_chemical_formula_sum 'C24 H35 I2 N O5'
_chemical_formula_weight 671.35
_space_group_IT_number 1
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall 'P 1'
_symmetry_space_group_name_H-M 'P 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 96.9997(19)
_cell_angle_beta 101.3959(18)
_cell_angle_gamma 96.5153(14)
_cell_formula_units_Z 1
_cell_length_a 8.3429(2)
_cell_length_b 8.7613(3)
_cell_length_c 9.7629(3)
_cell_measurement_reflns_used 2745
_cell_measurement_temperature 150
_cell_measurement_theta_max 27
_cell_measurement_theta_min 5
_cell_volume 687.36(4)
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection 'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature 150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_measurement_method \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.000
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 5243
_diffrn_reflns_theta_full 26.678
_diffrn_reflns_theta_max 27.503
_diffrn_reflns_theta_min 5.215
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 2.319
_exptl_absorpt_correction_T_max 0.85
_exptl_absorpt_correction_T_min 0.81
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.622
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 332
_exptl_crystal_size_max 0.11
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.07
_refine_diff_density_max 1.32
_refine_diff_density_min -0.78
_refine_ls_abs_structure_details 'Flack (1983), 2128 Friedel-pairs'
_refine_ls_abs_structure_Flack 0.052(18)
_refine_ls_extinction_method None
_refine_ls_goodness_of_fit_ref 1.0144
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 290
_refine_ls_number_reflns 5242
_refine_ls_number_restraints 3
_refine_ls_R_factor_all 0.0255
_refine_ls_R_factor_gt 0.0242
_refine_ls_shift/su_max 0.000105
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.64P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.0558
_refine_ls_wR_factor_gt 0.0546
_refine_ls_wR_factor_ref 0.0558
_reflns_limit_h_max 10
_reflns_limit_h_min -10
_reflns_limit_k_max 9
_reflns_limit_k_min -11
_reflns_limit_l_max 12
_reflns_limit_l_min -12
_reflns_number_gt 5061
_reflns_number_total 5243
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.11
_oxford_diffrn_Wilson_scale 2.54
_oxford_refine_ls_r_factor_ref 0.0255
_oxford_refine_ls_scale 0.6228(6)
_oxford_reflns_number_all 5242
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file ol103090z_si_002.cif
_cod_data_source_block 1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'P 1 '
_cod_original_formula_sum 'C24 H35 I2 N1 O5'
_cod_database_code 1501963
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
I1 I 0.04112(7) 0.22198(7) 0.17025(6) 0.0258 1.0000 Uani .
I2 I 0.64944(7) 1.08799(7) 0.26004(6) 0.0264 1.0000 Uani .
C3 C 0.4064(4) 0.9981(4) 0.2862(4) 0.0221 1.0000 Uani .
C4 C 0.4072(4) 0.9392(4) 0.4274(3) 0.0186 1.0000 Uani .
N5 N 0.2632(3) 0.8042(3) 0.3927(3) 0.0171 1.0000 Uani .
C6 C 0.2803(4) 0.7282(4) 0.2482(3) 0.0208 1.0000 Uani .
C7 C 0.3186(5) 0.8625(5) 0.1697(4) 0.0265 1.0000 Uani .
C8 C 0.2970(4) 0.7001(4) 0.5088(3) 0.0184 1.0000 Uani .
C9 C 0.4786(4) 0.7505(4) 0.5813(4) 0.0206 1.0000 Uani .
C10 C 0.5544(4) 0.8651(4) 0.4987(4) 0.0218 1.0000 Uani .
O11 O 0.4863(3) 0.8465(3) 0.7124(3) 0.0269 1.0000 Uani .
C12 C 0.6335(5) 0.9565(5) 0.7400(4) 0.0264 1.0000 Uani .
O13 O 0.6671(3) 0.9744(4) 0.6020(3) 0.0270 1.0000 Uani .
C14 C 0.5978(6) 1.1089(5) 0.8114(5) 0.0385 1.0000 Uani .
C15 C 0.7765(5) 0.8945(5) 0.8245(5) 0.0405 1.0000 Uani .
C16 C 0.2534(4) 0.5254(4) 0.4612(4) 0.0190 1.0000 Uani .
O17 O 0.3673(3) 0.4675(3) 0.3865(3) 0.0241 1.0000 Uani .
C18 C 0.2498(4) 0.4415(4) 0.5900(4) 0.0216 1.0000 Uani .
O19 O 0.1547(3) 0.5055(3) 0.6701(3) 0.0248 1.0000 Uani .
C20 C 0.1306(5) 0.4452(5) 0.8016(4) 0.0251 1.0000 Uani .
C21 C 0.0531(6) 0.2767(6) 0.7690(5) 0.0380 1.0000 Uani .
C22 C 0.2943(5) 0.4702(6) 0.9064(4) 0.0382 1.0000 Uani .
C23 C 0.0135(6) 0.5488(6) 0.8531(5) 0.0421 1.0000 Uani .
O24 O 0.3209(4) 0.3332(3) 0.6113(3) 0.0331 1.0000 Uani .
C25 C 0.0948(4) 0.8677(4) 0.3815(4) 0.0205 1.0000 Uani .
C26 C 0.0794(5) 0.9618(5) 0.5192(4) 0.0290 1.0000 Uani .
C27 C -0.0493(6) 0.7409(5) 0.3220(5) 0.0221 1.0000 Uani .
C28 C -0.1172(4) 0.6453(5) 0.4075(4) 0.0242 1.0000 Uani .
C29 C -0.2539(4) 0.5348(5) 0.3497(4) 0.0292 1.0000 Uani .
C30 C -0.3277(5) 0.5213(5) 0.2084(5) 0.0340 1.0000 Uani .
C31 C -0.2640(6) 0.6158(7) 0.1233(6) 0.0349 1.0000 Uani .
C32 C -0.1272(4) 0.7265(5) 0.1805(4) 0.0274 1.0000 Uani .
H31 H 0.3404 1.0837 0.2820 0.0270 1.0000 Uiso R
H41 H 0.3845 1.0216 0.4964 0.0201 1.0000 Uiso R
H62 H 0.1786 0.6608 0.2010 0.0230 1.0000 Uiso R
H61 H 0.3731 0.6700 0.2599 0.0235 1.0000 Uiso R
H72 H 0.2200 0.8906 0.1132 0.0302 1.0000 Uiso R
H71 H 0.3948 0.8351 0.1094 0.0301 1.0000 Uiso R
H81 H 0.2281 0.7312 0.5767 0.0205 1.0000 Uiso R
H91 H 0.5420 0.6631 0.5920 0.0219 1.0000 Uiso R
H101 H 0.6224 0.8209 0.4355 0.0270 1.0000 Uiso R
H142 H 0.6986 1.1823 0.8350 0.0560 1.0000 Uiso R
H143 H 0.5145 1.1464 0.7452 0.0559 1.0000 Uiso R
H141 H 0.5596 1.0907 0.8963 0.0561 1.0000 Uiso R
H153 H 0.8759 0.9670 0.8369 0.0571 1.0000 Uiso R
H151 H 0.7904 0.7958 0.7747 0.0572 1.0000 Uiso R
H152 H 0.7525 0.8822 0.9147 0.0570 1.0000 Uiso R
H161 H 0.1413 0.5038 0.3986 0.0240 1.0000 Uiso R
H221 H 0.2798 0.4414 0.9961 0.0520 1.0000 Uiso R
H222 H 0.3658 0.4047 0.8685 0.0518 1.0000 Uiso R
H223 H 0.3445 0.5767 0.9183 0.0522 1.0000 Uiso R
H251 H 0.0930 0.9402 0.3125 0.0259 1.0000 Uiso R
H261 H -0.0204 1.0070 0.5026 0.0430 1.0000 Uiso R
H262 H 0.0748 0.8917 0.5869 0.0432 1.0000 Uiso R
H263 H 0.1741 1.0398 0.5509 0.0433 1.0000 Uiso R
H281 H -0.0702 0.6580 0.5048 0.0304 1.0000 Uiso R
H291 H -0.2945 0.4653 0.4045 0.0361 1.0000 Uiso R
H301 H -0.4223 0.4512 0.1703 0.0380 1.0000 Uiso R
H311 H -0.3112 0.6047 0.0269 0.0346 1.0000 Uiso R
H321 H -0.0884 0.7931 0.1222 0.0335 1.0000 Uiso R
H171 H 0.3088 0.3933 0.3309 0.0382 1.0000 Uiso R
H231 H -0.0109 0.5194 0.9381 0.0538 1.0000 Uiso R
H232 H -0.0857 0.5371 0.7832 0.0538 1.0000 Uiso R
H233 H 0.0636 0.6542 0.8703 0.0538 1.0000 Uiso R
H211 H 0.0366 0.2367 0.8520 0.0824 1.0000 Uiso R
H212 H -0.0492 0.2637 0.7026 0.0824 1.0000 Uiso R
H213 H 0.1293 0.2225 0.7291 0.0824 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02450(14) 0.02669(17) 0.02557(14) 0.00675(12) 0.00416(11) 0.00026(12)
I2 0.02352(14) 0.02604(17) 0.03137(16) 0.00913(13) 0.00926(11) -0.00078(12)
C3 0.0199(16) 0.0211(19) 0.0248(17) 0.0059(14) 0.0041(13) -0.0008(14)
C4 0.0153(15) 0.0189(18) 0.0199(16) 0.0005(13) 0.0043(12) -0.0030(13)
N5 0.0159(13) 0.0157(15) 0.0184(13) 0.0008(11) 0.0027(10) 0.0003(11)
C6 0.0213(16) 0.0225(19) 0.0159(16) -0.0030(13) 0.0036(12) -0.0011(14)
C7 0.031(2) 0.028(2) 0.0194(17) 0.0029(15) 0.0072(15) -0.0030(16)
C8 0.0158(15) 0.0194(18) 0.0194(16) 0.0051(13) 0.0020(12) 0.0009(13)
C9 0.0178(16) 0.0169(19) 0.0246(17) 0.0032(14) -0.0006(13) 0.0005(14)
C10 0.0162(16) 0.0215(19) 0.0254(17) 0.0027(14) 0.0011(13) -0.0005(14)
O11 0.0278(14) 0.0285(17) 0.0192(13) 0.0004(11) 0.0005(11) -0.0068(12)
C12 0.0273(19) 0.024(2) 0.0242(18) 0.0044(15) -0.0008(14) -0.0035(15)
O13 0.0204(13) 0.0310(17) 0.0253(14) 0.0044(12) -0.0008(10) -0.0047(11)
C14 0.040(2) 0.033(3) 0.035(2) -0.0014(18) 0.0004(18) -0.0003(19)
C15 0.037(2) 0.034(3) 0.042(2) 0.011(2) -0.0123(18) -0.0009(19)
C16 0.0165(15) 0.0179(18) 0.0236(17) 0.0020(13) 0.0074(12) 0.0023(13)
O17 0.0224(12) 0.0213(14) 0.0311(14) 0.0016(10) 0.0120(10) 0.0047(10)
C18 0.0183(16) 0.0216(19) 0.0243(17) 0.0037(14) 0.0040(13) 0.0010(14)
O19 0.0293(15) 0.0238(15) 0.0263(14) 0.0087(11) 0.0123(11) 0.0081(12)
C20 0.033(2) 0.025(2) 0.0195(17) 0.0053(15) 0.0091(15) 0.0040(17)
C21 0.051(3) 0.033(3) 0.029(2) 0.0037(19) 0.0164(19) -0.012(2)
C22 0.038(2) 0.047(3) 0.028(2) 0.0008(19) 0.0051(17) 0.005(2)
C23 0.046(3) 0.053(3) 0.036(2) 0.010(2) 0.020(2) 0.020(2)
O24 0.0401(16) 0.0291(16) 0.0379(16) 0.0141(13) 0.0156(13) 0.0149(14)
C25 0.0173(16) 0.0197(19) 0.0247(17) 0.0042(14) 0.0031(13) 0.0049(14)
C26 0.0240(18) 0.026(2) 0.036(2) -0.0047(16) 0.0074(15) 0.0053(16)
C27 0.0163(19) 0.021(2) 0.027(2) 0.0010(17) 0.0042(15) -0.0019(16)
C28 0.0199(17) 0.025(2) 0.0306(19) 0.0076(15) 0.0071(14) 0.0075(15)
C29 0.0200(17) 0.023(2) 0.047(2) 0.0083(17) 0.0122(16) 0.0047(15)
C30 0.0173(18) 0.027(2) 0.052(3) -0.0026(19) 0.0027(16) -0.0022(16)
C31 0.022(2) 0.042(3) 0.032(2) 0.000(2) -0.0063(17) -0.002(2)
C32 0.0222(18) 0.032(2) 0.0272(19) 0.0071(16) 0.0016(14) 0.0030(16)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
I2 C3 C4 113.7(2) yes
I2 C3 C7 112.9(2) yes
C4 C3 C7 106.5(3) yes
I2 C3 H31 107.1 no
C4 C3 H31 107.8 no
C7 C3 H31 108.7 no
C3 C4 N5 104.0(3) yes
C3 C4 C10 120.4(3) yes
N5 C4 C10 103.3(3) yes
C3 C4 H41 109.9 no
N5 C4 H41 109.5 no
C10 C4 H41 108.9 no
C4 N5 C6 101.4(2) yes
C4 N5 C8 106.7(2) yes
C6 N5 C8 113.4(3) yes
C4 N5 C25 110.5(3) yes
C6 N5 C25 110.6(3) yes
C8 N5 C25 113.5(2) yes
N5 C6 C7 105.0(3) yes
N5 C6 H62 109.9 no
C7 C6 H62 112.5 no
N5 C6 H61 109.4 no
C7 C6 H61 108.9 no
H62 C6 H61 110.8 no
C3 C7 C6 105.0(3) yes
C3 C7 H72 110.9 no
C6 C7 H72 112.5 no
C3 C7 H71 109.1 no
C6 C7 H71 109.3 no
H72 C7 H71 109.9 no
N5 C8 C9 105.0(3) yes
N5 C8 C16 116.4(3) yes
C9 C8 C16 113.4(3) yes
N5 C8 H81 105.2 no
C9 C8 H81 108.3 no
C16 C8 H81 108.1 no
C8 C9 C10 108.4(3) yes
C8 C9 O11 108.5(3) yes
C10 C9 O11 101.6(3) yes
C8 C9 H91 113.4 no
C10 C9 H91 111.2 no
O11 C9 H91 113.0 no
C4 C10 C9 104.1(3) yes
C4 C10 O13 111.4(3) yes
C9 C10 O13 105.1(3) yes
C4 C10 H101 116.1 no
C9 C10 H101 114.9 no
O13 C10 H101 104.8 no
C9 O11 C12 107.6(3) yes
O11 C12 O13 105.2(3) yes
O11 C12 C14 108.1(3) yes
O13 C12 C14 110.2(3) yes
O11 C12 C15 110.9(3) yes
O13 C12 C15 108.6(3) yes
C14 C12 C15 113.5(4) yes
C12 O13 C10 108.7(3) yes
C12 C14 H142 108.6 no
C12 C14 H143 107.8 no
H142 C14 H143 110.1 no
C12 C14 H141 108.8 no
H142 C14 H141 110.2 no
H143 C14 H141 111.3 no
C12 C15 H153 109.8 no
C12 C15 H151 109.3 no
H153 C15 H151 109.5 no
C12 C15 H152 107.9 no
H153 C15 H152 109.6 no
H151 C15 H152 110.7 no
C8 C16 O17 111.3(3) yes
C8 C16 C18 109.9(3) yes
O17 C16 C18 109.5(3) yes
C8 C16 H161 108.8 no
O17 C16 H161 108.9 no
C18 C16 H161 108.3 no
C16 O17 H171 102.0 no
C16 C18 O19 110.4(3) yes
C16 C18 O24 123.3(3) yes
O19 C18 O24 126.3(3) yes
C18 O19 C20 121.1(3) yes
O19 C20 C21 110.6(3) yes
O19 C20 C22 109.1(3) yes
C21 C20 C22 112.6(4) yes
O19 C20 C23 102.3(3) yes
C21 C20 C23 111.3(4) yes
C22 C20 C23 110.4(4) yes
C20 C21 H211 111.5 no
C20 C21 H212 111.2 no
H211 C21 H212 109.5 no
C20 C21 H213 105.6 no
H211 C21 H213 109.5 no
H212 C21 H213 109.5 no
C20 C22 H221 110.6 no
C20 C22 H222 107.7 no
H221 C22 H222 109.0 no
C20 C22 H223 110.3 no
H221 C22 H223 110.5 no
H222 C22 H223 108.6 no
C20 C23 H231 109.3 no
C20 C23 H232 109.3 no
H231 C23 H232 109.5 no
C20 C23 H233 109.8 no
H231 C23 H233 109.5 no
H232 C23 H233 109.5 no
N5 C25 C26 112.9(3) yes
N5 C25 C27 111.7(3) yes
C26 C25 C27 113.0(3) yes
N5 C25 H251 105.8 no
C26 C25 H251 106.3 no
C27 C25 H251 106.5 no
C25 C26 H261 108.7 no
C25 C26 H262 107.7 no
H261 C26 H262 109.9 no
C25 C26 H263 108.7 no
H261 C26 H263 111.4 no
H262 C26 H263 110.4 no
C25 C27 C28 122.1(4) yes
C25 C27 C32 119.3(4) yes
C28 C27 C32 118.4(4) yes
C27 C28 C29 120.3(4) yes
C27 C28 H281 119.5 no
C29 C28 H281 120.2 no
C28 C29 C30 120.2(4) yes
C28 C29 H291 120.7 no
C30 C29 H291 119.0 no
C29 C30 C31 120.2(4) yes
C29 C30 H301 120.5 no
C31 C30 H301 119.2 no
C30 C31 C32 119.9(4) yes
C30 C31 H311 120.6 no
C32 C31 H311 119.6 no
C27 C32 C31 121.0(4) yes
C27 C32 H321 120.2 no
C31 C32 H321 118.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I2 C3 2.165(3) yes
C3 C4 1.529(5) yes
C3 C7 1.545(5) yes
C3 H31 0.979 no
C4 N5 1.541(4) yes
C4 C10 1.539(5) yes
C4 H41 0.986 no
N5 C6 1.525(4) yes
N5 C8 1.542(4) yes
N5 C25 1.558(4) yes
C6 C7 1.519(5) yes
C6 H62 0.973 no
C6 H61 0.970 no
C7 H72 0.970 no
C7 H71 0.978 no
C8 C9 1.530(4) yes
C8 C16 1.525(5) yes
C8 H81 0.993 no
C9 C10 1.521(5) yes
C9 O11 1.429(4) yes
C9 H91 0.983 no
C10 O13 1.416(5) yes
C10 H101 0.991 no
O11 C12 1.431(5) yes
C12 O13 1.452(4) yes
C12 C14 1.517(6) yes
C12 C15 1.505(5) yes
C14 H142 0.969 no
C14 H143 0.967 no
C14 H141 0.970 no
C15 H153 0.963 no
C15 H151 0.970 no
C15 H152 0.957 no
C16 O17 1.409(4) yes
C16 C18 1.535(5) yes
C16 H161 0.995 no
O17 H171 0.832 no
C18 O19 1.340(4) yes
C18 O24 1.192(5) yes
O19 C20 1.486(4) yes
C20 C21 1.512(6) yes
C20 C22 1.511(6) yes
C20 C23 1.522(6) yes
C21 H211 0.950 no
C21 H212 0.950 no
C21 H213 0.950 no
C22 H221 0.966 no
C22 H222 0.967 no
C22 H223 0.962 no
C23 H231 0.950 no
C23 H232 0.950 no
C23 H233 0.950 no
C25 C26 1.525(5) yes
C25 C27 1.510(6) yes
C25 H251 0.980 no
C26 H261 0.956 no
C26 H262 0.958 no
C26 H263 0.957 no
C27 C28 1.403(6) yes
C27 C32 1.389(6) yes
C28 C29 1.385(5) yes
C28 H281 0.941 no
C29 C30 1.381(6) yes
C29 H291 0.936 no
C30 C31 1.377(7) yes
C30 H301 0.926 no
C31 C32 1.386(7) yes
C31 H311 0.935 no
C32 H321 0.938 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C21 H213 O24 125 0.95 2.34 2.984(6) yes
|
1501964.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501964.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501964
loop_
_publ_author_name
'Brock, E. Anne'
'Davies, Stephen G.'
'Lee, James A.'
'Roberts, Paul M.'
'Thomson, James E.'
_publ_section_title
;
Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular
iodoamination with concomitant N-debenzylation.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1594
_journal_page_last 1597
_journal_paper_doi 10.1021/ol103090z
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_moiety 'C16 H27 I2 N1 O5'
_chemical_formula_sum 'C16 H27 I2 N O5'
_chemical_formula_weight 567.20
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 11.4404(3)
_cell_length_b 12.2759(3)
_cell_length_c 14.3996(4)
_cell_measurement_reflns_used 2572
_cell_measurement_temperature 1
_cell_measurement_theta_max 27
_cell_measurement_theta_min 5
_cell_volume 2022.30(9)
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection 'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature 1
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device 'Nonius KappaCCD'
_diffrn_measurement_device_type Area
_diffrn_measurement_method \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.000
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 4605
_diffrn_reflns_theta_full 27.460
_diffrn_reflns_theta_max 27.460
_diffrn_reflns_theta_min 5.180
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 3.134
_exptl_absorpt_correction_T_max 0.94
_exptl_absorpt_correction_T_min 0.94
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.863
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1104
_exptl_crystal_size_max 0.05
_exptl_crystal_size_mid 0.02
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.76
_refine_diff_density_min -1.03
_refine_ls_extinction_method None
_refine_ls_goodness_of_fit_ref 0.8829
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 217
_refine_ls_number_reflns 4587
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0439
_refine_ls_R_factor_gt 0.0377
_refine_ls_shift/su_max 0.000550
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 7.01P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.0898
_refine_ls_wR_factor_gt 0.0842
_refine_ls_wR_factor_ref 0.0898
_reflns_limit_h_max 14
_reflns_limit_h_min -14
_reflns_limit_k_max 15
_reflns_limit_k_min 0
_reflns_limit_l_max 18
_reflns_limit_l_min 0
_reflns_number_gt 4149
_reflns_number_total 4587
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.57
_oxford_diffrn_Wilson_scale 35.01
_oxford_refine_ls_r_factor_ref 0.0439
_oxford_refine_ls_scale 0.16888(8)
_oxford_reflns_number_all 4587
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file ol103090z_si_003.cif
_cod_data_source_block 1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'P 21 21 21 '
_cod_original_formula_sum 'C16 H27 I2 N1 O5'
_cod_database_code 1501964
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
I1 I 0.46152(3) 0.49548(3) 0.37839(2) 0.0316 1.0000 Uani .
I2 I 0.63514(3) 0.48377(3) 0.65127(3) 0.0364 1.0000 Uani .
C3 C 0.7988(4) 0.3951(4) 0.6551(4) 0.0233 1.0000 Uani .
C4 C 0.8065(4) 0.3038(4) 0.5848(4) 0.0218 1.0000 Uani .
N5 N 0.7643(3) 0.2024(3) 0.6384(3) 0.0197 1.0000 Uani .
C6 C 0.6708(4) 0.1455(4) 0.5825(3) 0.0162 1.0000 Uani .
C7 C 0.6313(5) 0.2289(4) 0.5096(3) 0.0187 1.0000 Uani .
C8 C 0.7355(4) 0.3043(4) 0.4958(3) 0.0207 1.0000 Uani .
O9 O 0.7999(3) 0.2462(3) 0.4256(3) 0.0239 1.0000 Uani .
C10 C 0.7182(4) 0.1906(4) 0.3670(3) 0.0218 1.0000 Uani .
O11 O 0.6129(3) 0.1782(3) 0.4216(2) 0.0218 1.0000 Uani .
C12 C 0.6906(5) 0.2576(5) 0.2818(4) 0.0336 1.0000 Uani .
C13 C 0.7698(5) 0.0790(4) 0.3436(5) 0.0328 1.0000 Uani .
C14 C 0.5724(4) 0.0951(4) 0.6411(3) 0.0184 1.0000 Uani .
O15 O 0.4939(3) 0.1745(3) 0.6755(2) 0.0234 1.0000 Uani .
C16 C 0.5101(4) 0.0080(4) 0.5830(3) 0.0202 1.0000 Uani .
O17 O 0.5832(3) -0.0718(3) 0.5646(3) 0.0240 1.0000 Uani .
C18 C 0.5477(4) -0.1733(4) 0.5159(4) 0.0231 1.0000 Uani .
C19 C 0.4687(5) -0.2368(4) 0.5798(4) 0.0282 1.0000 Uani .
C20 C 0.6635(5) -0.2301(5) 0.5017(4) 0.0279 1.0000 Uani .
C21 C 0.4898(5) -0.1480(5) 0.4236(4) 0.0345 1.0000 Uani .
O22 O 0.4087(3) 0.0160(3) 0.5613(3) 0.0297 1.0000 Uani .
C23 C 0.7397(4) 0.2364(4) 0.7372(3) 0.0239 1.0000 Uani .
C24 C 0.8137(5) 0.3376(5) 0.7479(4) 0.0283 1.0000 Uani .
H31 H 0.8608 0.4456 0.6433 0.0339 1.0000 Uiso R
H41 H 0.8889 0.2933 0.5684 0.0248 1.0000 Uiso R
H61 H 0.7083 0.0857 0.5489 0.0192 1.0000 Uiso R
H71 H 0.5614 0.2685 0.5304 0.0232 1.0000 Uiso R
H81 H 0.7132 0.3787 0.4760 0.0252 1.0000 Uiso R
H122 H 0.6390 0.2172 0.2424 0.0510 1.0000 Uiso R
H121 H 0.7625 0.2731 0.2494 0.0511 1.0000 Uiso R
H123 H 0.6540 0.3247 0.2999 0.0511 1.0000 Uiso R
H132 H 0.7152 0.0391 0.3050 0.0521 1.0000 Uiso R
H131 H 0.8418 0.0889 0.3101 0.0519 1.0000 Uiso R
H133 H 0.7850 0.0397 0.4007 0.0522 1.0000 Uiso R
H141 H 0.6090 0.0602 0.6959 0.0223 1.0000 Uiso R
H193 H 0.4548 -0.3078 0.5534 0.0431 1.0000 Uiso R
H192 H 0.5050 -0.2445 0.6398 0.0428 1.0000 Uiso R
H191 H 0.3955 -0.1985 0.5861 0.0431 1.0000 Uiso R
H203 H 0.6510 -0.2999 0.4729 0.0459 1.0000 Uiso R
H202 H 0.7021 -0.2402 0.5602 0.0459 1.0000 Uiso R
H201 H 0.7117 -0.1856 0.4622 0.0462 1.0000 Uiso R
H211 H 0.4829 -0.2135 0.3878 0.0512 1.0000 Uiso R
H213 H 0.4136 -0.1176 0.4350 0.0510 1.0000 Uiso R
H212 H 0.5377 -0.0974 0.3907 0.0511 1.0000 Uiso R
H231 H 0.7625 0.1800 0.7813 0.0303 1.0000 Uiso R
H232 H 0.6569 0.2522 0.7438 0.0299 1.0000 Uiso R
H242 H 0.8951 0.3193 0.7571 0.0322 1.0000 Uiso R
H241 H 0.7873 0.3834 0.7988 0.0318 1.0000 Uiso R
H52 H 0.8253 0.1558 0.6407 0.0298 1.0000 Uiso R
H151 H 0.4417 0.1732 0.6359 0.0351 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02714(16) 0.02510(18) 0.0425(2) 0.00466(15) -0.00242(12) -0.00755(14)
I2 0.0472(2) 0.02583(19) 0.03619(19) -0.00540(15) -0.00002(15) 0.01296(16)
C3 0.026(2) 0.020(2) 0.023(2) -0.001(2) 0.002(2) -0.0058(18)
C4 0.017(2) 0.025(3) 0.023(2) 0.003(2) 0.0021(19) -0.0020(19)
N5 0.0189(18) 0.018(2) 0.022(2) -0.0034(16) -0.0041(16) -0.0026(14)
C6 0.013(2) 0.013(2) 0.022(2) -0.0039(18) -0.0025(17) -0.0003(16)
C7 0.023(2) 0.016(2) 0.018(2) -0.0004(18) 0.002(2) -0.001(2)
C8 0.021(2) 0.020(3) 0.022(2) 0.002(2) 0.0041(19) -0.0021(19)
O9 0.0211(17) 0.0236(19) 0.0269(19) -0.0061(15) 0.0035(15) -0.0052(15)
C10 0.020(2) 0.025(2) 0.020(2) -0.0037(19) 0.0029(19) -0.0064(19)
O11 0.0211(16) 0.0276(19) 0.0168(16) -0.0039(14) -0.0002(14) -0.0067(14)
C12 0.035(3) 0.038(3) 0.029(3) 0.001(3) 0.002(2) -0.002(3)
C13 0.035(3) 0.022(3) 0.041(3) -0.012(3) 0.002(3) 0.004(2)
C14 0.020(2) 0.013(2) 0.022(2) -0.0015(18) 0.0020(19) 0.0006(17)
O15 0.0213(16) 0.0231(18) 0.0258(19) -0.0004(14) -0.0006(14) 0.0008(13)
C16 0.0190(19) 0.021(2) 0.020(2) 0.004(2) -0.0010(16) -0.003(2)
O17 0.0183(15) 0.0149(17) 0.039(2) -0.0072(15) -0.0011(15) -0.0011(13)
C18 0.025(2) 0.016(2) 0.028(3) -0.0012(19) 0.000(2) -0.001(2)
C19 0.032(3) 0.020(3) 0.032(3) 0.001(2) 0.003(2) -0.006(2)
C20 0.030(3) 0.025(3) 0.029(3) -0.005(2) 0.002(2) 0.007(2)
C21 0.038(3) 0.036(3) 0.029(3) -0.006(3) -0.004(2) 0.004(2)
O22 0.0209(15) 0.024(2) 0.044(2) -0.0048(18) -0.0047(14) 0.0023(15)
C23 0.027(3) 0.030(3) 0.015(2) 0.000(2) -0.005(2) -0.001(2)
C24 0.028(3) 0.029(3) 0.028(3) -0.002(2) -0.009(2) -0.005(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
I2 C3 C4 113.9(3) yes
I2 C3 C24 110.7(3) yes
C4 C3 C24 103.8(4) yes
I2 C3 H31 108.2 no
C4 C3 H31 108.5 no
C24 C3 H31 111.9 no
C3 C4 N5 104.2(4) yes
C3 C4 C8 122.1(4) yes
N5 C4 C8 105.0(4) yes
C3 C4 H41 108.3 no
N5 C4 H41 108.4 no
C8 C4 H41 108.2 no
C4 N5 C6 109.1(4) yes
C4 N5 C23 107.9(4) yes
C6 N5 C23 119.9(4) yes
C4 N5 H52 106.8 no
C6 N5 H52 105.8 no
C23 N5 H52 106.6 no
N5 C6 C7 105.3(4) yes
N5 C6 C14 114.3(4) yes
C7 C6 C14 115.3(4) yes
N5 C6 H61 107.5 no
C7 C6 H61 107.0 no
C14 C6 H61 107.0 no
C6 C7 C8 105.3(4) yes
C6 C7 O11 111.0(4) yes
C8 C7 O11 105.3(4) yes
C6 C7 H71 111.2 no
C8 C7 H71 112.1 no
O11 C7 H71 111.5 no
C7 C8 C4 107.8(4) yes
C7 C8 O9 101.1(4) yes
C4 C8 O9 108.5(4) yes
C7 C8 H81 113.4 no
C4 C8 H81 112.6 no
O9 C8 H81 112.8 no
C8 O9 C10 108.4(3) yes
O9 C10 O11 105.9(4) yes
O9 C10 C12 110.9(4) yes
O11 C10 C12 109.0(4) yes
O9 C10 C13 107.7(4) yes
O11 C10 C13 110.3(4) yes
C12 C10 C13 112.9(5) yes
C10 O11 C7 108.3(4) yes
C10 C12 H122 109.2 no
C10 C12 H121 108.8 no
H122 C12 H121 109.9 no
C10 C12 H123 109.8 no
H122 C12 H123 109.6 no
H121 C12 H123 109.5 no
C10 C13 H132 109.3 no
C10 C13 H131 109.1 no
H132 C13 H131 109.2 no
C10 C13 H133 109.1 no
H132 C13 H133 110.5 no
H131 C13 H133 109.6 no
C6 C14 O15 112.4(4) yes
C6 C14 C16 108.7(4) yes
O15 C14 C16 112.1(4) yes
C6 C14 H141 107.6 no
O15 C14 H141 106.7 no
C16 C14 H141 109.2 no
C14 O15 H151 101.8 no
C14 C16 O17 109.5(3) yes
C14 C16 O22 122.1(5) yes
O17 C16 O22 128.4(5) yes
C16 O17 C18 123.1(4) yes
O17 C18 C19 108.0(4) yes
O17 C18 C20 102.2(4) yes
C19 C18 C20 111.7(5) yes
O17 C18 C21 111.2(4) yes
C19 C18 C21 112.3(4) yes
C20 C18 C21 111.0(5) yes
C18 C19 H193 109.0 no
C18 C19 H192 109.9 no
H193 C19 H192 109.6 no
C18 C19 H191 109.1 no
H193 C19 H191 109.5 no
H192 C19 H191 109.8 no
C18 C20 H203 109.8 no
C18 C20 H202 110.1 no
H203 C20 H202 109.4 no
C18 C20 H201 108.7 no
H203 C20 H201 109.6 no
H202 C20 H201 109.2 no
C18 C21 H211 109.6 no
C18 C21 H213 108.9 no
H211 C21 H213 110.0 no
C18 C21 H212 108.5 no
H211 C21 H212 109.1 no
H213 C21 H212 110.7 no
N5 C23 C24 102.7(4) yes
N5 C23 H231 111.5 no
C24 C23 H231 111.6 no
N5 C23 H232 109.2 no
C24 C23 H232 111.9 no
H231 C23 H232 109.8 no
C3 C24 C23 103.2(4) yes
C3 C24 H242 109.7 no
C23 C24 H242 111.3 no
C3 C24 H241 111.1 no
C23 C24 H241 112.2 no
H242 C24 H241 109.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I2 C3 2.166(5) yes
C3 C4 1.513(7) yes
C3 C24 1.521(7) yes
C3 H31 0.957 no
C4 N5 1.542(6) yes
C4 C8 1.517(7) yes
C4 H41 0.981 no
N5 C6 1.511(5) yes
N5 C23 1.509(6) yes
N5 H52 0.903 no
C6 C7 1.535(7) yes
C6 C14 1.537(6) yes
C6 H61 0.978 no
C7 C8 1.522(7) yes
C7 O11 1.427(6) yes
C7 H71 0.982 no
C8 O9 1.440(6) yes
C8 H81 0.991 no
O9 C10 1.432(6) yes
C10 O11 1.446(6) yes
C10 C12 1.510(8) yes
C10 C13 1.530(7) yes
C12 H122 0.958 no
C12 H121 0.964 no
C12 H123 0.961 no
C13 H132 0.968 no
C13 H131 0.963 no
C13 H133 0.968 no
C14 O15 1.415(5) yes
C14 C16 1.534(6) yes
C14 H141 0.992 no
O15 H151 0.825 no
C16 O17 1.315(6) yes
C16 O22 1.206(5) yes
O17 C18 1.486(6) yes
C18 C19 1.507(7) yes
C18 C20 1.512(7) yes
C18 C21 1.518(8) yes
C19 H193 0.964 no
C19 H192 0.963 no
C19 H191 0.964 no
C20 H203 0.962 no
C20 H202 0.959 no
C20 H201 0.962 no
C21 H211 0.958 no
C21 H213 0.963 no
C21 H212 0.954 no
C23 C24 1.512(7) yes
C23 H231 0.975 no
C23 H232 0.971 no
C24 H242 0.967 no
C24 H241 0.971 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 H41 O11 2_556 157 0.98 2.59 3.515(7) yes
C23 H232 O15 . 131 0.97 2.31 3.045(7) yes
O15 H151 O9 2_456 147 0.83 2.10 2.827(7) yes
|
1501965.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501965.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501965
loop_
_publ_author_name
'Notte, Gregory T.'
'Baxter Vu, Jenny M.'
'Leighton, James L.'
_publ_section_title
;
Highly enantioselective Mannich reactions with \a-aryl silyl ketene
acetals and imines.
;
_journal_issue 4
_journal_name_full 'Organic letters'
_journal_page_first 816
_journal_page_last 818
_journal_paper_doi 10.1021/ol103096u
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C29 H28.5 F3 I N3 O1.75'
_chemical_formula_weight 630.95
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 101.8140(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 13.5694(5)
_cell_length_b 17.6210(6)
_cell_length_c 24.7835(9)
_cell_measurement_reflns_used 9962
_cell_measurement_temperature 125(2)
_cell_measurement_theta_max 31.77
_cell_measurement_theta_min 2.50
_cell_volume 5800.4(4)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0336
_diffrn_reflns_av_sigmaI/netI 0.0463
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_k_min -25
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_number 94260
_diffrn_reflns_theta_full 30.51
_diffrn_reflns_theta_max 30.51
_diffrn_reflns_theta_min 1.43
_exptl_absorpt_coefficient_mu 1.152
_exptl_absorpt_correction_T_max 0.9135
_exptl_absorpt_correction_T_min 0.6752
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour COLORLESS
_exptl_crystal_density_diffrn 1.445
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description BLOCK
_exptl_crystal_F_000 2540
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.08
_platon_squeeze_details
;
The unit cell contains 6 diethylether molecules which have been treated
as a diffuse contribution to the overall scattering without specific
atom positions by SQUEEZE/PLATON.
;
_refine_diff_density_max 1.295
_refine_diff_density_min -0.888
_refine_diff_density_rms 0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.007(7)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.986
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 1226
_refine_ls_number_reflns 35372
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 0.986
_refine_ls_R_factor_all 0.0618
_refine_ls_R_factor_gt 0.0420
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0912
_refine_ls_wR_factor_ref 0.0979
_reflns_number_gt 26330
_reflns_number_total 35372
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103096u_si_001.cif
_cod_data_source_block jbws10p
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.
'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_original_formula_sum 'C29 H28.50 F3 I N3 O1.75'
_cod_database_code 1501965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.408610(15) 0.563852(13) 0.056517(9) 0.04196(6) Uani 1 1 d .
F1 F -0.1019(3) 0.45403(18) 0.19969(16) 0.1268(16) Uani 1 1 d .
F2 F -0.1158(2) 0.56246(18) 0.22454(9) 0.0775(8) Uani 1 1 d .
F3 F -0.2324(2) 0.5181(2) 0.16491(12) 0.1127(14) Uani 1 1 d .
O1 O 0.03705(15) 0.71236(11) 0.00075(9) 0.0296(4) Uani 1 1 d .
N1 N 0.15483(19) 0.78716(15) -0.13699(11) 0.0349(6) Uani 1 1 d .
N2 N 0.19773(16) 0.65145(13) -0.02905(9) 0.0215(4) Uani 1 1 d .
N3 N 0.14733(16) 0.61466(12) 0.00664(8) 0.0209(4) Uani 1 1 d .
H3A H 0.1676 0.5701 0.0208 0.025 Uiso 1 1 calc R
C1 C 0.2045(2) 0.73529(16) -0.12241(12) 0.0271(6) Uani 1 1 d .
C2 C 0.27348(19) 0.67169(15) -0.10250(11) 0.0224(5) Uani 1 1 d .
C3 C 0.3476(2) 0.69970(17) -0.05062(11) 0.0284(6) Uani 1 1 d .
H3B H 0.4063 0.6653 -0.0412 0.034 Uiso 1 1 calc R
H3C H 0.3719 0.7515 -0.0563 0.034 Uiso 1 1 calc R
C4 C 0.28581(19) 0.69919(16) -0.00507(11) 0.0257(5) Uani 1 1 d .
H4A H 0.2606 0.7520 -0.0019 0.031 Uiso 1 1 calc R
C5 C 0.21526(18) 0.60955(15) -0.07674(10) 0.0201(5) Uani 1 1 d .
H5A H 0.2611 0.5658 -0.0642 0.024 Uiso 1 1 calc R
C6 C 0.06624(19) 0.64920(14) 0.01907(10) 0.0202(5) Uani 1 1 d .
C7 C -0.1322(3) 0.5203(2) 0.18108(15) 0.0484(9) Uani 1 1 d .
C8 C 0.3437(2) 0.67605(18) 0.05160(13) 0.0321(6) Uani 1 1 d .
H8A H 0.2978 0.6791 0.0778 0.039 Uiso 1 1 calc R
H8B H 0.3985 0.7132 0.0637 0.039 Uiso 1 1 calc R
C9 C 0.3991(2) 0.5795(2) -0.23432(13) 0.0461(9) Uani 1 1 d .
H9A H 0.4259 0.5580 -0.2634 0.055 Uiso 1 1 calc R
C10 C 0.4421(2) 0.5626(2) -0.18046(13) 0.0462(8) Uani 1 1 d .
H10A H 0.4996 0.5306 -0.1725 0.055 Uiso 1 1 calc R
C11 C 0.4021(2) 0.5922(2) -0.13794(12) 0.0375(7) Uani 1 1 d .
H11A H 0.4312 0.5793 -0.1009 0.045 Uiso 1 1 calc R
C12 C 0.3192(2) 0.64086(17) -0.14916(11) 0.0263(6) Uani 1 1 d .
C13 C 0.2771(2) 0.65681(18) -0.20389(12) 0.0304(6) Uani 1 1 d .
H13A H 0.2195 0.6887 -0.2122 0.036 Uiso 1 1 calc R
C14 C 0.3167(2) 0.6276(2) -0.24630(12) 0.0367(7) Uani 1 1 d .
H14A H 0.2880 0.6403 -0.2834 0.044 Uiso 1 1 calc R
C15 C 0.12014(18) 0.58103(14) -0.11394(10) 0.0201(5) Uani 1 1 d .
C16 C 0.02980(19) 0.61995(15) -0.12131(11) 0.0226(5) Uani 1 1 d .
H16A H 0.0255 0.6658 -0.1017 0.027 Uiso 1 1 calc R
C17 C -0.0551(2) 0.59196(17) -0.15753(11) 0.0265(6) Uani 1 1 d .
H17A H -0.1170 0.6189 -0.1627 0.032 Uiso 1 1 calc R
C18 C -0.0489(2) 0.52484(18) -0.18593(11) 0.0291(6) Uani 1 1 d .
H18A H -0.1064 0.5060 -0.2108 0.035 Uiso 1 1 calc R
C19 C 0.0410(2) 0.48540(18) -0.17795(11) 0.0297(6) Uani 1 1 d .
H19A H 0.0449 0.4389 -0.1969 0.036 Uiso 1 1 calc R
C20 C 0.1251(2) 0.51342(15) -0.14256(11) 0.0243(5) Uani 1 1 d .
H20A H 0.1869 0.4864 -0.1377 0.029 Uiso 1 1 calc R
C21 C 0.0154(2) 0.60936(15) 0.05879(11) 0.0234(5) Uani 1 1 d .
C22 C 0.0689(2) 0.56625(18) 0.10252(10) 0.0293(6) Uani 1 1 d .
H22A H 0.1389 0.5574 0.1056 0.035 Uiso 1 1 calc R
C23 C 0.0196(2) 0.53684(18) 0.14099(12) 0.0345(7) Uani 1 1 d .
H23A H 0.0556 0.5079 0.1710 0.041 Uiso 1 1 calc R
C24 C -0.0832(2) 0.54939(17) 0.13610(12) 0.0329(7) Uani 1 1 d .
C25 C -0.1368(2) 0.58843(17) 0.09245(13) 0.0337(7) Uani 1 1 d .
H25A H -0.2074 0.5948 0.0888 0.040 Uiso 1 1 calc R
C26 C -0.0882(2) 0.61911(16) 0.05312(12) 0.0279(6) Uani 1 1 d .
H26A H -0.1254 0.6465 0.0226 0.033 Uiso 1 1 calc R
I101 I 0.35203(2) 0.328798(19) -0.124277(12) 0.06780(9) Uani 1 1 d .
F101 F -0.38049(14) 0.48171(14) -0.08296(9) 0.0549(6) Uani 1 1 d .
F102 F -0.38917(15) 0.41183(17) -0.01374(11) 0.0715(8) Uani 1 1 d .
F103 F -0.35690(17) 0.52908(18) -0.00209(12) 0.0823(8) Uani 1 1 d .
O101 O 0.15177(14) 0.45182(10) 0.00456(8) 0.0245(4) Uani 1 1 d .
N101 N 0.30468(19) 0.14447(15) 0.11242(12) 0.0359(6) Uani 1 1 d .
N102 N 0.20022(14) 0.29524(12) 0.01571(9) 0.0194(4) Uani 1 1 d .
N103 N 0.10459(15) 0.32789(12) -0.00081(9) 0.0193(4) Uani 1 1 d .
H10B H 0.0534 0.2973 -0.0124 0.023 Uiso 1 1 calc R
C101 C 0.32813(19) 0.19955(15) 0.09461(12) 0.0251(5) Uani 1 1 d .
C102 C 0.35652(18) 0.27037(15) 0.06976(11) 0.0215(5) Uani 1 1 d .
C103 C 0.3609(2) 0.25508(17) 0.00813(11) 0.0273(6) Uani 1 1 d .
H10C H 0.4176 0.2833 -0.0020 0.033 Uiso 1 1 calc R
H10D H 0.3706 0.2003 0.0021 0.033 Uiso 1 1 calc R
C104 C 0.25985(19) 0.28225(15) -0.02695(11) 0.0240(5) Uani 1 1 d .
H10E H 0.2287 0.2405 -0.0521 0.029 Uiso 1 1 calc R
C105 C 0.26702(18) 0.32789(14) 0.06434(10) 0.0182(5) Uani 1 1 d .
H10F H 0.2901 0.3791 0.0548 0.022 Uiso 1 1 calc R
C106 C 0.08586(19) 0.40253(14) -0.00022(10) 0.0187(5) Uani 1 1 d .
C107 C -0.3375(2) 0.4691(2) -0.03004(15) 0.0415(8) Uani 1 1 d .
C108 C 0.2701(2) 0.35308(18) -0.06053(13) 0.0349(7) Uani 1 1 d .
H10G H 0.3057 0.3930 -0.0359 0.042 Uiso 1 1 calc R
H10H H 0.2023 0.3724 -0.0774 0.042 Uiso 1 1 calc R
C109 C 0.6193(2) 0.3737(2) 0.17005(14) 0.0405(8) Uani 1 1 d .
H10I H 0.6766 0.3973 0.1922 0.049 Uiso 1 1 calc R
C110 C 0.5835(2) 0.39849(18) 0.11700(14) 0.0345(7) Uani 1 1 d .
H11B H 0.6166 0.4387 0.1023 0.041 Uiso 1 1 calc R
C111 C 0.49858(19) 0.36441(17) 0.08474(12) 0.0271(6) Uani 1 1 d .
H11C H 0.4729 0.3824 0.0485 0.033 Uiso 1 1 calc R
C112 C 0.45140(18) 0.30425(15) 0.10548(11) 0.0229(5) Uani 1 1 d .
C113 C 0.4881(2) 0.27917(16) 0.15882(12) 0.0290(6) Uani 1 1 d .
H11D H 0.4562 0.2381 0.1733 0.035 Uiso 1 1 calc R
C114 C 0.5717(2) 0.31421(19) 0.19115(13) 0.0380(7) Uani 1 1 d .
H11E H 0.5963 0.2973 0.2278 0.046 Uiso 1 1 calc R
C115 C 0.21968(18) 0.33457(15) 0.11379(10) 0.0211(5) Uani 1 1 d .
C116 C 0.14500(19) 0.28558(15) 0.12336(11) 0.0244(5) Uani 1 1 d .
H11F H 0.1205 0.2469 0.0974 0.029 Uiso 1 1 calc R
C117 C 0.1055(2) 0.29300(18) 0.17140(12) 0.0300(6) Uani 1 1 d .
H11G H 0.0537 0.2598 0.1776 0.036 Uiso 1 1 calc R
C118 C 0.1424(2) 0.34886(18) 0.20949(12) 0.0325(7) Uani 1 1 d .
H11H H 0.1171 0.3531 0.2424 0.039 Uiso 1 1 calc R
C119 C 0.2152(2) 0.39802(17) 0.20001(12) 0.0313(6) Uani 1 1 d .
H11I H 0.2399 0.4361 0.2265 0.038 Uiso 1 1 calc R
C120 C 0.2536(2) 0.39302(16) 0.15193(11) 0.0266(6) Uani 1 1 d .
H12A H 0.3021 0.4286 0.1450 0.032 Uiso 1 1 calc R
C121 C -0.02453(19) 0.42072(14) -0.00625(10) 0.0199(5) Uani 1 1 d .
C122 C -0.06847(19) 0.46979(15) -0.04822(11) 0.0242(5) Uani 1 1 d .
H12B H -0.0288 0.4928 -0.0711 0.029 Uiso 1 1 calc R
C123 C -0.1711(2) 0.48488(17) -0.05645(12) 0.0287(6) Uani 1 1 d .
H12C H -0.2025 0.5172 -0.0856 0.034 Uiso 1 1 calc R
C124 C -0.2271(2) 0.45215(16) -0.02161(12) 0.0263(6) Uani 1 1 d .
C125 C -0.1823(2) 0.40569(15) 0.02123(11) 0.0251(5) Uani 1 1 d .
H12D H -0.2210 0.3851 0.0456 0.030 Uiso 1 1 calc R
C126 C -0.0805(2) 0.38910(15) 0.02857(11) 0.0239(5) Uani 1 1 d .
H12E H -0.0496 0.3561 0.0574 0.029 Uiso 1 1 calc R
I201 I -0.402186(17) 0.526146(14) -0.543276(10) 0.04726(6) Uani 1 1 d .
F201 F 0.2396(2) 0.50215(19) -0.65196(12) 0.0864(9) Uani 1 1 d .
F202 F 0.1033(2) 0.50207(18) -0.71130(9) 0.0836(10) Uani 1 1 d .
F203 F 0.1470(2) 0.40661(15) -0.65948(12) 0.0850(9) Uani 1 1 d .
O201 O -0.03944(15) 0.67429(11) -0.48435(8) 0.0292(4) Uani 1 1 d .
N201 N -0.1528(2) 0.72083(19) -0.32927(15) 0.0561(9) Uani 1 1 d .
N202 N -0.19258(17) 0.60526(14) -0.45170(10) 0.0285(5) Uani 1 1 d .
N203 N -0.14431(16) 0.57344(13) -0.49059(9) 0.0246(5) Uani 1 1 d .
H20B H -0.1647 0.5301 -0.5067 0.030 Uiso 1 1 calc R
C201 C -0.2021(2) 0.6717(2) -0.34923(14) 0.0394(8) Uani 1 1 d .
C202 C -0.2677(2) 0.60955(17) -0.37589(13) 0.0314(6) Uani 1 1 d .
C203 C -0.3428(2) 0.6444(2) -0.42606(13) 0.0368(7) Uani 1 1 d .
H20C H -0.4011 0.6104 -0.4382 0.044 Uiso 1 1 calc R
H20D H -0.3677 0.6944 -0.4163 0.044 Uiso 1 1 calc R
C204 C -0.2820(2) 0.65310(17) -0.47146(13) 0.0331(6) Uani 1 1 d .
H20E H -0.2580 0.7069 -0.4702 0.040 Uiso 1 1 calc R
C205 C -0.20544(19) 0.55577(17) -0.40632(11) 0.0268(5) Uani 1 1 d .
H20F H -0.2475 0.5110 -0.4213 0.032 Uiso 1 1 calc R
C206 C -0.0652(2) 0.61112(16) -0.50289(11) 0.0244(5) Uani 1 1 d .
C207 C 0.1424(3) 0.4819(2) -0.66150(15) 0.0506(9) Uani 1 1 d .
C208 C -0.3391(3) 0.6385(2) -0.52937(15) 0.0410(8) Uani 1 1 d .
H20G H -0.2933 0.6471 -0.5551 0.049 Uiso 1 1 calc R
H20H H -0.3945 0.6760 -0.5383 0.049 Uiso 1 1 calc R
C209 C -0.3931(2) 0.4800(2) -0.25946(14) 0.0446(8) Uani 1 1 d .
H20I H -0.4198 0.4501 -0.2339 0.053 Uiso 1 1 calc R
C210 C -0.4218(3) 0.4653(2) -0.31458(15) 0.0471(9) Uani 1 1 d .
H21A H -0.4673 0.4251 -0.3271 0.057 Uiso 1 1 calc R
C211 C -0.3842(2) 0.5095(2) -0.35237(14) 0.0392(8) Uani 1 1 d .
H21B H -0.4062 0.5004 -0.3907 0.047 Uiso 1 1 calc R
C212 C -0.3149(2) 0.5667(2) -0.33440(11) 0.0324(6) Uani 1 1 d .
C213 C -0.2875(2) 0.5809(2) -0.27793(12) 0.0375(7) Uani 1 1 d .
H21C H -0.2419 0.6208 -0.2647 0.045 Uiso 1 1 calc R
C214 C -0.3272(2) 0.5362(2) -0.24057(13) 0.0460(9) Uani 1 1 d .
H21D H -0.3079 0.5455 -0.2021 0.055 Uiso 1 1 calc R
C215 C -0.1060(2) 0.52860(17) -0.37206(11) 0.0268(5) Uani 1 1 d .
C216 C -0.0187(2) 0.57238(18) -0.36698(11) 0.0300(6) Uani 1 1 d .
H21E H -0.0208 0.6201 -0.3850 0.036 Uiso 1 1 calc R
C217 C 0.0719(2) 0.54536(18) -0.33509(12) 0.0346(7) Uani 1 1 d .
H21F H 0.1318 0.5745 -0.3316 0.041 Uiso 1 1 calc R
C218 C 0.0737(2) 0.4766(2) -0.30891(12) 0.0386(8) Uani 1 1 d .
H21G H 0.1352 0.4587 -0.2872 0.046 Uiso 1 1 calc R
C219 C -0.0118(3) 0.4330(2) -0.31342(12) 0.0377(7) Uani 1 1 d .
H21H H -0.0092 0.3856 -0.2949 0.045 Uiso 1 1 calc R
C220 C -0.1018(2) 0.45890(18) -0.34527(12) 0.0314(6) Uani 1 1 d .
H22B H -0.1608 0.4288 -0.3488 0.038 Uiso 1 1 calc R
C221 C -0.01474(19) 0.57335(15) -0.54340(10) 0.0229(5) Uani 1 1 d .
C222 C -0.0669(2) 0.53429(17) -0.58955(11) 0.0292(6) Uani 1 1 d .
H22C H -0.1376 0.5274 -0.5947 0.035 Uiso 1 1 calc R
C223 C -0.0150(2) 0.50559(18) -0.62779(12) 0.0351(7) Uani 1 1 d .
H22D H -0.0503 0.4799 -0.6596 0.042 Uiso 1 1 calc R
C224 C 0.0881(2) 0.51452(17) -0.61946(12) 0.0335(7) Uani 1 1 d .
C225 C 0.1415(2) 0.55062(16) -0.57311(11) 0.0287(6) Uani 1 1 d .
H22E H 0.2127 0.5547 -0.5673 0.034 Uiso 1 1 calc R
C226 C 0.0903(2) 0.58081(16) -0.53514(11) 0.0276(6) Uani 1 1 d .
H22F H 0.1263 0.6066 -0.5035 0.033 Uiso 1 1 calc R
I301 I -0.33358(2) 0.268356(19) -0.371509(11) 0.06637(9) Uani 1 1 d .
F301 F 0.36533(18) 0.4740(2) -0.50124(15) 0.1133(14) Uani 1 1 d .
F302 F 0.39482(16) 0.35837(18) -0.48117(12) 0.0806(9) Uani 1 1 d .
F303 F 0.38823(15) 0.43757(15) -0.41786(10) 0.0636(7) Uani 1 1 d .
O301 O -0.14535(14) 0.41036(11) -0.49827(8) 0.0268(4) Uani 1 1 d .
N301 N -0.3003(2) 0.10424(15) -0.60943(11) 0.0369(6) Uani 1 1 d .
N302 N -0.19835(15) 0.25602(13) -0.51862(8) 0.0202(4) Uani 1 1 d .
N303 N -0.10154(15) 0.28592(12) -0.50209(9) 0.0210(4) Uani 1 1 d .
H30A H -0.0509 0.2539 -0.4938 0.025 Uiso 1 1 calc R
C301 C -0.3241(2) 0.16078(17) -0.59337(11) 0.0267(6) Uani 1 1 d .
C302 C -0.35420(19) 0.23300(15) -0.57178(11) 0.0233(5) Uani 1 1 d .
C303 C -0.3608(2) 0.21932(18) -0.51025(11) 0.0301(6) Uani 1 1 d .
H30B H -0.4133 0.2520 -0.4999 0.036 Uiso 1 1 calc R
H30C H -0.3775 0.1656 -0.5044 0.036 Uiso 1 1 calc R
C304 C -0.2557(2) 0.23958(16) -0.47541(11) 0.0247(5) Uani 1 1 d .
H30D H -0.2264 0.1937 -0.4543 0.030 Uiso 1 1 calc R
C305 C -0.26463(18) 0.29092(15) -0.56592(10) 0.0207(5) Uani 1 1 d .
H30E H -0.2873 0.3415 -0.5549 0.025 Uiso 1 1 calc R
C306 C -0.08061(19) 0.36123(15) -0.49797(10) 0.0217(5) Uani 1 1 d .
C307 C 0.3448(2) 0.4195(2) -0.46884(16) 0.0456(9) Uani 1 1 d .
C308 C -0.2579(3) 0.3039(2) -0.43589(13) 0.0379(7) Uani 1 1 d .
H30F H -0.2937 0.3478 -0.4558 0.045 Uiso 1 1 calc R
H30G H -0.1883 0.3198 -0.4195 0.045 Uiso 1 1 calc R
C309 C -0.6241(2) 0.3238(2) -0.67338(15) 0.0452(8) Uani 1 1 d .
H30H H -0.6834 0.3445 -0.6957 0.054 Uiso 1 1 calc R
C310 C -0.5848(2) 0.3553(2) -0.62222(17) 0.0448(8) Uani 1 1 d .
H31A H -0.6174 0.3974 -0.6094 0.054 Uiso 1 1 calc R
C311 C -0.4987(2) 0.32587(18) -0.58991(13) 0.0335(6) Uani 1 1 d .
H31B H -0.4716 0.3482 -0.5551 0.040 Uiso 1 1 calc R
C312 C -0.45079(19) 0.26338(17) -0.60783(11) 0.0259(5) Uani 1 1 d .
C313 C -0.4903(2) 0.23316(18) -0.65956(12) 0.0327(6) Uani 1 1 d .
H31C H -0.4572 0.1919 -0.6730 0.039 Uiso 1 1 calc R
C314 C -0.5775(2) 0.2628(2) -0.69174(13) 0.0411(7) Uani 1 1 d .
H31D H -0.6050 0.2408 -0.7266 0.049 Uiso 1 1 calc R
C315 C -0.21830(18) 0.30035(15) -0.61537(10) 0.0214(5) Uani 1 1 d .
C316 C -0.14626(19) 0.25054(16) -0.62733(11) 0.0253(5) Uani 1 1 d .
H31E H -0.1251 0.2088 -0.6035 0.030 Uiso 1 1 calc R
C317 C -0.1044(2) 0.26101(18) -0.67389(11) 0.0281(6) Uani 1 1 d .
H31F H -0.0550 0.2268 -0.6816 0.034 Uiso 1 1 calc R
C318 C -0.1361(2) 0.32238(18) -0.70890(11) 0.0329(7) Uani 1 1 d .
H31G H -0.1094 0.3296 -0.7411 0.039 Uiso 1 1 calc R
C319 C -0.2067(2) 0.37249(18) -0.69642(12) 0.0333(7) Uani 1 1 d .
H31H H -0.2268 0.4149 -0.7197 0.040 Uiso 1 1 calc R
C320 C -0.2483(2) 0.36164(17) -0.65044(11) 0.0290(6) Uani 1 1 d .
H32A H -0.2974 0.3961 -0.6428 0.035 Uiso 1 1 calc R
C321 C 0.02983(19) 0.37800(15) -0.49171(11) 0.0227(5) Uani 1 1 d .
C322 C 0.0774(2) 0.42248(16) -0.44776(11) 0.0275(6) Uani 1 1 d .
H32B H 0.0396 0.4440 -0.4232 0.033 Uiso 1 1 calc R
C323 C 0.1801(2) 0.43535(18) -0.43978(12) 0.0322(6) Uani 1 1 d .
H32C H 0.2133 0.4648 -0.4093 0.039 Uiso 1 1 calc R
C324 C 0.2342(2) 0.40499(17) -0.47657(13) 0.0313(6) Uani 1 1 d .
C325 C 0.1864(2) 0.36262(17) -0.52138(12) 0.0293(6) Uani 1 1 d .
H32D H 0.2234 0.3438 -0.5472 0.035 Uiso 1 1 calc R
C326 C 0.0845(2) 0.34773(15) -0.52850(12) 0.0269(6) Uani 1 1 d .
H32E H 0.0519 0.3170 -0.5583 0.032 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03394(10) 0.04328(12) 0.04438(11) 0.00735(10) -0.00199(8) 0.00882(9)
F1 0.211(4) 0.0645(19) 0.146(3) 0.054(2) 0.133(3) 0.019(2)
F2 0.0954(18) 0.103(2) 0.0455(12) -0.0119(14) 0.0418(12) -0.0363(17)
F3 0.0708(18) 0.201(4) 0.0681(17) 0.038(2) 0.0190(14) -0.068(2)
O1 0.0332(11) 0.0232(10) 0.0360(11) 0.0090(8) 0.0153(9) 0.0082(8)
N1 0.0327(13) 0.0327(14) 0.0411(15) 0.0061(11) 0.0116(11) 0.0014(11)
N2 0.0190(10) 0.0247(11) 0.0217(11) 0.0009(9) 0.0063(8) -0.0009(8)
N3 0.0245(11) 0.0188(10) 0.0202(10) 0.0059(8) 0.0062(8) 0.0039(8)
C1 0.0245(13) 0.0291(14) 0.0292(14) 0.0024(11) 0.0088(11) -0.0022(11)
C2 0.0194(12) 0.0253(13) 0.0239(13) 0.0018(10) 0.0077(10) -0.0001(10)
C3 0.0221(13) 0.0344(15) 0.0283(14) 0.0024(12) 0.0040(11) -0.0061(11)
C4 0.0226(13) 0.0262(14) 0.0277(14) -0.0025(11) 0.0036(10) -0.0046(11)
C5 0.0172(11) 0.0242(13) 0.0197(12) 0.0016(10) 0.0055(9) -0.0002(10)
C6 0.0202(12) 0.0192(12) 0.0214(12) 0.0020(10) 0.0050(9) 0.0012(9)
C7 0.062(2) 0.050(2) 0.0419(19) 0.0004(17) 0.0288(17) -0.0165(18)
C8 0.0265(14) 0.0341(16) 0.0338(16) -0.0056(12) 0.0016(12) -0.0004(12)
C9 0.0343(16) 0.073(3) 0.0349(16) 0.0005(16) 0.0160(13) 0.0172(17)
C10 0.0410(17) 0.062(2) 0.0392(17) 0.0089(18) 0.0171(14) 0.0206(18)
C11 0.0347(16) 0.055(2) 0.0239(14) 0.0097(13) 0.0092(12) 0.0171(15)
C12 0.0200(12) 0.0338(15) 0.0261(13) 0.0048(11) 0.0068(10) 0.0002(11)
C13 0.0208(13) 0.0405(16) 0.0297(14) 0.0036(12) 0.0045(11) 0.0035(12)
C14 0.0284(15) 0.055(2) 0.0251(15) 0.0009(14) 0.0024(12) 0.0028(14)
C15 0.0175(11) 0.0244(14) 0.0186(11) 0.0034(9) 0.0045(9) -0.0025(9)
C16 0.0230(12) 0.0229(13) 0.0226(12) 0.0017(10) 0.0066(10) -0.0010(10)
C17 0.0196(12) 0.0330(14) 0.0247(13) 0.0058(11) -0.0007(10) 0.0008(11)
C18 0.0308(14) 0.0331(15) 0.0204(12) 0.0014(12) -0.0019(10) -0.0057(13)
C19 0.0387(16) 0.0306(15) 0.0204(13) -0.0013(11) 0.0076(11) -0.0023(13)
C20 0.0236(12) 0.0240(14) 0.0264(13) 0.0016(10) 0.0081(10) 0.0011(10)
C21 0.0284(13) 0.0215(13) 0.0226(12) 0.0010(10) 0.0106(10) 0.0013(10)
C22 0.0323(14) 0.0336(14) 0.0235(12) 0.0022(12) 0.0089(10) 0.0015(13)
C23 0.0459(17) 0.0312(15) 0.0259(14) 0.0064(12) 0.0064(12) -0.0013(14)
C24 0.0452(17) 0.0288(16) 0.0301(14) -0.0049(11) 0.0198(13) -0.0132(13)
C25 0.0326(15) 0.0300(15) 0.0418(17) -0.0019(13) 0.0157(13) -0.0043(12)
C26 0.0279(14) 0.0248(13) 0.0328(15) 0.0018(11) 0.0108(11) -0.0007(11)
I101 0.0852(2) 0.0788(2) 0.05494(16) 0.01436(14) 0.05060(15) 0.01642(16)
F101 0.0264(9) 0.0763(15) 0.0579(13) 0.0282(12) -0.0009(9) 0.0012(10)
F102 0.0229(10) 0.105(2) 0.0881(18) 0.0483(16) 0.0138(10) -0.0050(11)
F103 0.0437(13) 0.106(2) 0.099(2) -0.0199(17) 0.0173(13) 0.0358(14)
O101 0.0221(9) 0.0187(9) 0.0325(10) 0.0037(8) 0.0050(8) -0.0008(7)
N101 0.0324(13) 0.0260(13) 0.0474(16) 0.0046(11) 0.0034(11) 0.0006(11)
N102 0.0129(9) 0.0215(10) 0.0245(11) -0.0040(8) 0.0053(8) 0.0029(8)
N103 0.0157(9) 0.0180(10) 0.0229(10) -0.0006(8) 0.0009(8) 0.0001(8)
C101 0.0179(12) 0.0223(13) 0.0337(15) -0.0023(11) 0.0020(10) 0.0024(10)
C102 0.0178(11) 0.0200(12) 0.0266(13) 0.0000(10) 0.0042(9) 0.0018(10)
C103 0.0227(13) 0.0300(15) 0.0308(14) -0.0078(12) 0.0089(11) 0.0039(11)
C104 0.0260(13) 0.0249(14) 0.0227(12) -0.0027(10) 0.0085(10) -0.0004(10)
C105 0.0178(11) 0.0155(11) 0.0218(12) -0.0022(10) 0.0051(9) 0.0009(9)
C106 0.0209(12) 0.0202(12) 0.0145(11) 0.0009(9) 0.0028(9) 0.0002(10)
C107 0.0244(15) 0.046(2) 0.055(2) 0.0135(16) 0.0104(14) 0.0050(14)
C108 0.0373(16) 0.0334(16) 0.0386(17) 0.0052(13) 0.0184(13) 0.0033(13)
C109 0.0282(15) 0.0439(18) 0.0443(19) -0.0008(15) -0.0047(13) -0.0049(14)
C110 0.0267(14) 0.0307(15) 0.0456(18) 0.0013(13) 0.0064(13) -0.0072(12)
C111 0.0179(12) 0.0321(15) 0.0301(14) 0.0021(12) 0.0020(10) 0.0008(11)
C112 0.0162(11) 0.0230(13) 0.0291(13) -0.0020(10) 0.0039(10) 0.0039(10)
C113 0.0257(13) 0.0277(15) 0.0325(15) 0.0033(11) 0.0031(11) 0.0027(11)
C114 0.0336(16) 0.0409(19) 0.0343(16) 0.0038(13) -0.0055(13) 0.0001(13)
C115 0.0203(12) 0.0222(12) 0.0203(12) 0.0027(10) 0.0030(9) 0.0048(10)
C116 0.0228(12) 0.0266(14) 0.0245(13) -0.0047(10) 0.0065(10) -0.0016(10)
C117 0.0291(14) 0.0374(16) 0.0260(14) 0.0006(12) 0.0115(11) -0.0014(12)
C118 0.0366(16) 0.0391(17) 0.0231(14) -0.0055(12) 0.0093(12) 0.0017(13)
C119 0.0385(16) 0.0317(15) 0.0246(14) -0.0086(11) 0.0086(12) -0.0022(13)
C120 0.0266(13) 0.0250(14) 0.0273(14) -0.0042(11) 0.0033(11) -0.0017(11)
C121 0.0188(12) 0.0189(12) 0.0207(12) -0.0002(10) 0.0008(9) 0.0000(9)
C122 0.0217(12) 0.0249(13) 0.0263(13) 0.0077(11) 0.0059(10) 0.0010(10)
C123 0.0218(13) 0.0341(15) 0.0293(14) 0.0080(12) 0.0036(11) 0.0065(11)
C124 0.0194(12) 0.0304(14) 0.0287(14) 0.0037(11) 0.0041(10) -0.0002(11)
C125 0.0272(13) 0.0207(13) 0.0295(14) 0.0020(10) 0.0105(11) -0.0004(10)
C126 0.0254(13) 0.0228(13) 0.0236(13) 0.0029(10) 0.0048(10) 0.0020(10)
I201 0.03778(12) 0.05619(14) 0.04563(12) -0.01005(11) 0.00344(9) -0.00975(10)
F201 0.0641(16) 0.123(3) 0.0849(19) -0.0362(18) 0.0449(14) 0.0127(16)
F202 0.106(2) 0.116(2) 0.0355(12) 0.0085(13) 0.0310(13) 0.0627(19)
F203 0.138(3) 0.0528(15) 0.0761(18) -0.0161(13) 0.0503(18) 0.0317(16)
O201 0.0345(11) 0.0210(10) 0.0346(11) -0.0091(8) 0.0134(9) -0.0068(8)
N201 0.0410(16) 0.0487(18) 0.083(2) -0.0386(18) 0.0232(16) -0.0055(14)
N202 0.0249(11) 0.0277(12) 0.0362(13) -0.0040(10) 0.0139(10) 0.0017(10)
N203 0.0258(11) 0.0216(11) 0.0290(11) -0.0087(9) 0.0113(9) -0.0037(9)
C201 0.0257(15) 0.0456(19) 0.051(2) -0.0210(16) 0.0164(14) 0.0005(14)
C202 0.0222(13) 0.0332(15) 0.0406(16) -0.0152(13) 0.0106(12) -0.0014(11)
C203 0.0252(14) 0.0429(18) 0.0446(18) -0.0087(14) 0.0126(13) 0.0069(13)
C204 0.0280(15) 0.0260(14) 0.0484(18) -0.0021(13) 0.0152(13) 0.0021(12)
C205 0.0227(12) 0.0296(14) 0.0300(13) -0.0097(12) 0.0096(10) -0.0047(11)
C206 0.0211(12) 0.0256(14) 0.0263(13) -0.0067(11) 0.0042(10) -0.0011(10)
C207 0.065(3) 0.055(2) 0.0378(19) -0.0115(17) 0.0238(17) 0.0119(19)
C208 0.0369(17) 0.0393(18) 0.047(2) 0.0040(15) 0.0100(15) 0.0035(14)
C209 0.0346(17) 0.063(2) 0.0403(18) 0.0048(17) 0.0178(14) 0.0110(17)
C210 0.0372(18) 0.062(2) 0.048(2) -0.0113(18) 0.0223(15) -0.0100(17)
C211 0.0300(15) 0.053(2) 0.0362(16) -0.0109(14) 0.0115(12) -0.0085(14)
C212 0.0238(12) 0.0451(17) 0.0288(13) -0.0116(14) 0.0069(10) 0.0042(14)
C213 0.0242(14) 0.053(2) 0.0336(15) -0.0111(14) 0.0011(12) 0.0073(13)
C214 0.0318(16) 0.076(3) 0.0297(15) -0.0102(16) 0.0048(12) 0.0094(17)
C215 0.0267(13) 0.0294(14) 0.0261(13) -0.0090(12) 0.0100(10) -0.0018(12)
C216 0.0264(13) 0.0355(16) 0.0297(14) -0.0130(12) 0.0094(10) -0.0023(12)
C217 0.0249(13) 0.046(2) 0.0325(15) -0.0156(13) 0.0043(11) -0.0015(12)
C218 0.0347(16) 0.053(2) 0.0259(15) -0.0098(14) 0.0011(12) 0.0096(15)
C219 0.0489(19) 0.0413(18) 0.0228(14) -0.0043(13) 0.0074(13) 0.0070(15)
C220 0.0362(16) 0.0364(16) 0.0244(14) -0.0106(12) 0.0125(12) -0.0046(13)
C221 0.0248(12) 0.0209(13) 0.0243(12) -0.0026(10) 0.0082(10) -0.0025(10)
C222 0.0296(14) 0.0282(14) 0.0291(14) -0.0055(12) 0.0042(11) -0.0016(12)
C223 0.0438(18) 0.0343(16) 0.0263(14) -0.0091(12) 0.0052(12) -0.0001(13)
C224 0.0471(18) 0.0299(16) 0.0287(14) -0.0065(12) 0.0197(13) 0.0049(13)
C225 0.0284(13) 0.0269(15) 0.0333(14) -0.0033(11) 0.0124(11) 0.0006(11)
C226 0.0276(13) 0.0279(15) 0.0277(13) -0.0054(11) 0.0064(11) -0.0025(11)
I301 0.0911(2) 0.07566(19) 0.04689(14) -0.00921(13) 0.04812(15) -0.01043(17)
F301 0.0367(13) 0.161(3) 0.137(3) 0.090(3) 0.0034(15) -0.0289(17)
F302 0.0316(12) 0.111(2) 0.101(2) -0.0452(18) 0.0184(12) 0.0052(13)
F303 0.0252(10) 0.0929(19) 0.0677(15) -0.0218(14) -0.0021(10) -0.0070(11)
O301 0.0261(10) 0.0212(9) 0.0330(10) -0.0053(8) 0.0059(8) 0.0011(8)
N301 0.0387(14) 0.0285(14) 0.0448(15) 0.0015(12) 0.0118(12) -0.0017(11)
N302 0.0189(10) 0.0263(11) 0.0159(10) 0.0032(8) 0.0050(8) 0.0013(9)
N303 0.0188(10) 0.0225(11) 0.0200(10) -0.0009(8) 0.0003(8) -0.0003(8)
C301 0.0256(13) 0.0286(14) 0.0269(14) 0.0019(11) 0.0075(11) -0.0050(11)
C302 0.0208(12) 0.0249(13) 0.0256(13) -0.0026(10) 0.0078(10) -0.0039(10)
C303 0.0294(15) 0.0394(16) 0.0239(14) 0.0047(12) 0.0114(11) -0.0081(13)
C304 0.0240(13) 0.0304(14) 0.0227(13) 0.0038(10) 0.0117(10) 0.0002(11)
C305 0.0184(12) 0.0216(12) 0.0223(12) -0.0004(10) 0.0044(9) 0.0010(10)
C306 0.0230(12) 0.0265(13) 0.0161(11) -0.0019(10) 0.0048(9) -0.0012(10)
C307 0.0233(15) 0.059(2) 0.055(2) 0.0044(18) 0.0094(15) -0.0006(15)
C308 0.0452(18) 0.0402(17) 0.0337(16) -0.0054(13) 0.0206(14) -0.0052(14)
C309 0.0252(15) 0.059(2) 0.048(2) 0.0141(18) -0.0004(14) 0.0014(15)
C310 0.0258(15) 0.0372(18) 0.072(3) 0.0073(17) 0.0103(15) 0.0050(13)
C311 0.0205(13) 0.0353(16) 0.0425(17) -0.0039(14) 0.0014(12) -0.0009(12)
C312 0.0185(12) 0.0272(13) 0.0322(14) 0.0009(12) 0.0061(10) -0.0044(11)
C313 0.0292(15) 0.0400(17) 0.0297(15) 0.0005(12) 0.0077(12) -0.0045(13)
C314 0.0295(15) 0.060(2) 0.0325(16) 0.0047(15) 0.0039(12) -0.0094(15)
C315 0.0197(12) 0.0237(12) 0.0194(12) 0.0008(10) 0.0005(9) -0.0062(10)
C316 0.0243(13) 0.0307(15) 0.0210(12) 0.0024(10) 0.0047(10) -0.0018(11)
C317 0.0251(13) 0.0341(15) 0.0260(13) -0.0029(12) 0.0072(11) -0.0032(12)
C318 0.0374(16) 0.0418(17) 0.0199(13) 0.0015(12) 0.0069(11) -0.0137(14)
C319 0.0394(16) 0.0311(15) 0.0276(14) 0.0090(12) 0.0029(12) -0.0076(13)
C320 0.0313(14) 0.0292(14) 0.0250(13) 0.0024(11) 0.0022(11) -0.0020(12)
C321 0.0223(12) 0.0202(12) 0.0247(13) -0.0020(10) 0.0027(10) -0.0022(10)
C322 0.0258(13) 0.0305(14) 0.0259(14) -0.0062(11) 0.0051(11) -0.0010(11)
C323 0.0252(14) 0.0382(17) 0.0301(15) -0.0051(12) -0.0015(11) -0.0044(12)
C324 0.0214(13) 0.0324(15) 0.0399(16) 0.0078(13) 0.0061(12) -0.0004(11)
C325 0.0286(14) 0.0323(15) 0.0302(15) 0.0008(12) 0.0134(11) -0.0048(12)
C326 0.0322(14) 0.0229(13) 0.0265(14) -0.0037(10) 0.0082(11) -0.0030(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 N2 C5 117.8(2)
N3 N2 C4 118.2(2)
C5 N2 C4 111.2(2)
C6 N3 N2 117.9(2)
N1 C1 C2 176.6(3)
C1 C2 C12 110.3(2)
C1 C2 C3 107.2(2)
C12 C2 C3 116.8(2)
C1 C2 C5 109.2(2)
C12 C2 C5 112.3(2)
C3 C2 C5 100.5(2)
C4 C3 C2 104.4(2)
N2 C4 C8 116.1(2)
N2 C4 C3 103.0(2)
C8 C4 C3 115.1(2)
N2 C5 C15 113.8(2)
N2 C5 C2 99.0(2)
C15 C5 C2 115.1(2)
O1 C6 N3 122.6(2)
O1 C6 C21 120.7(2)
N3 C6 C21 116.7(2)
F2 C7 F1 103.6(4)
F2 C7 F3 105.0(3)
F1 C7 F3 108.1(4)
F2 C7 C24 113.3(3)
F1 C7 C24 114.7(3)
F3 C7 C24 111.4(3)
C4 C8 I1 115.2(2)
C10 C9 C14 120.3(3)
C9 C10 C11 120.2(3)
C10 C11 C12 120.4(3)
C13 C12 C11 118.2(3)
C13 C12 C2 121.3(2)
C11 C12 C2 120.4(2)
C14 C13 C12 121.6(3)
C13 C14 C9 119.3(3)
C16 C15 C20 119.3(2)
C16 C15 C5 122.6(2)
C20 C15 C5 118.0(2)
C15 C16 C17 120.1(3)
C18 C17 C16 120.0(3)
C19 C18 C17 119.9(2)
C20 C19 C18 120.1(3)
C19 C20 C15 120.6(3)
C26 C21 C22 119.8(2)
C26 C21 C6 118.0(2)
C22 C21 C6 122.1(2)
C23 C22 C21 119.6(3)
C22 C23 C24 120.1(3)
C25 C24 C23 120.8(3)
C25 C24 C7 121.2(3)
C23 C24 C7 118.0(3)
C24 C25 C26 120.0(3)
C25 C26 C21 119.6(3)
N103 N102 C105 117.25(19)
N103 N102 C104 117.7(2)
C105 N102 C104 108.18(19)
C106 N103 N102 124.5(2)
N101 C101 C102 178.2(3)
C101 C102 C112 110.5(2)
C101 C102 C103 109.1(2)
C112 C102 C103 115.9(2)
C101 C102 C105 108.6(2)
C112 C102 C105 110.1(2)
C103 C102 C105 102.2(2)
C104 C103 C102 106.8(2)
N102 C104 C108 112.9(2)
N102 C104 C103 101.5(2)
C108 C104 C103 113.1(2)
N102 C105 C115 113.9(2)
N102 C105 C102 98.88(19)
C115 C105 C102 115.8(2)
O101 C106 N103 123.8(2)
O101 C106 C121 123.0(2)
N103 C106 C121 113.2(2)
F103 C107 F102 105.8(3)
F103 C107 F101 106.7(3)
F102 C107 F101 105.7(3)
F103 C107 C124 112.8(3)
F102 C107 C124 112.2(3)
F101 C107 C124 113.1(3)
C104 C108 I101 110.90(19)
C110 C109 C114 119.9(3)
C109 C110 C111 119.9(3)
C112 C111 C110 120.3(3)
C113 C112 C111 119.5(2)
C113 C112 C102 121.6(2)
C111 C112 C102 118.8(2)
C112 C113 C114 119.9(3)
C109 C114 C113 120.3(3)
C116 C115 C120 119.3(2)
C116 C115 C105 122.7(2)
C120 C115 C105 118.0(2)
C115 C116 C117 120.3(2)
C118 C117 C116 119.6(3)
C119 C118 C117 120.4(3)
C118 C119 C120 120.9(3)
C119 C120 C115 119.3(3)
C126 C121 C122 120.9(2)
C126 C121 C106 121.0(2)
C122 C121 C106 118.1(2)
C121 C122 C123 119.5(2)
C124 C123 C122 119.3(2)
C125 C124 C123 120.9(2)
C125 C124 C107 119.8(3)
C123 C124 C107 119.3(3)
C124 C125 C126 119.8(3)
C121 C126 C125 119.6(2)
N203 N202 C205 116.1(2)
N203 N202 C204 118.2(2)
C205 N202 C204 112.1(2)
C206 N203 N202 117.9(2)
N201 C201 C202 178.6(4)
C201 C202 C212 111.3(3)
C201 C202 C205 109.3(2)
C212 C202 C205 111.7(2)
C201 C202 C203 107.4(3)
C212 C202 C203 115.9(2)
C205 C202 C203 100.6(2)
C204 C203 C202 105.1(2)
N202 C204 C208 116.5(3)
N202 C204 C203 103.3(2)
C208 C204 C203 115.6(3)
N202 C205 C215 112.7(2)
N202 C205 C202 99.8(2)
C215 C205 C202 115.3(2)
O201 C206 N203 122.8(2)
O201 C206 C221 121.6(2)
N203 C206 C221 115.5(2)
F202 C207 F203 108.6(3)
F202 C207 F201 107.1(4)
F203 C207 F201 102.9(3)
F202 C207 C224 113.1(3)
F203 C207 C224 112.3(3)
F201 C207 C224 112.3(3)
C204 C208 I201 114.8(2)
C214 C209 C210 121.2(3)
C209 C210 C211 119.9(3)
C212 C211 C210 120.5(3)
C211 C212 C213 118.3(3)
C211 C212 C202 119.7(3)
C213 C212 C202 121.9(3)
C212 C213 C214 120.2(3)
C209 C214 C213 119.9(3)
C220 C215 C216 119.5(3)
C220 C215 C205 119.4(3)
C216 C215 C205 121.1(3)
C215 C216 C217 119.5(3)
C218 C217 C216 119.6(3)
C217 C218 C219 121.5(3)
C218 C219 C220 119.4(3)
C219 C220 C215 120.5(3)
C222 C221 C226 119.6(2)
C222 C221 C206 123.3(2)
C226 C221 C206 117.1(2)
C223 C222 C221 119.8(3)
C224 C223 C222 119.8(3)
C223 C224 C225 121.3(3)
C223 C224 C207 118.5(3)
C225 C224 C207 120.1(3)
C224 C225 C226 119.4(3)
C225 C226 C221 120.0(3)
N303 N302 C305 117.7(2)
N303 N302 C304 117.7(2)
C305 N302 C304 109.65(19)
C306 N303 N302 124.1(2)
N301 C301 C302 179.1(3)
C301 C302 C312 111.1(2)
C301 C302 C303 107.3(2)
C312 C302 C303 114.3(2)
C301 C302 C305 109.2(2)
C312 C302 C305 112.5(2)
C303 C302 C305 102.0(2)
C304 C303 C302 106.1(2)
N302 C304 C308 114.2(2)
N302 C304 C303 101.7(2)
C308 C304 C303 113.4(2)
N302 C305 C315 114.3(2)
N302 C305 C302 98.0(2)
C315 C305 C302 116.3(2)
O301 C306 N303 123.3(2)
O301 C306 C321 123.8(2)
N303 C306 C321 112.9(2)
F301 C307 F303 107.4(3)
F301 C307 F302 105.5(3)
F303 C307 F302 105.3(3)
F301 C307 C324 112.2(3)
F303 C307 C324 113.8(3)
F302 C307 C324 112.1(3)
C304 C308 I301 109.9(2)
C314 C309 C310 120.0(3)
C311 C310 C309 120.2(3)
C310 C311 C312 120.5(3)
C313 C312 C311 118.6(3)
C313 C312 C302 121.9(3)
C311 C312 C302 119.4(2)
C314 C313 C312 120.6(3)
C309 C314 C313 120.1(3)
C316 C315 C320 119.0(2)
C316 C315 C305 122.4(2)
C320 C315 C305 118.6(2)
C315 C316 C317 121.0(3)
C318 C317 C316 119.2(3)
C319 C318 C317 119.6(3)
C318 C319 C320 120.9(3)
C319 C320 C315 120.3(3)
C322 C321 C326 120.3(2)
C322 C321 C306 119.0(2)
C326 C321 C306 120.7(2)
C323 C322 C321 119.8(3)
C322 C323 C324 119.7(3)
C325 C324 C323 120.6(3)
C325 C324 C307 119.2(3)
C323 C324 C307 120.1(3)
C326 C325 C324 119.8(3)
C325 C326 C321 119.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C8 2.157(3)
F1 C7 1.291(5)
F2 C7 1.290(4)
F3 C7 1.336(5)
O1 C6 1.236(3)
N1 C1 1.149(4)
N2 N3 1.385(3)
N2 C5 1.454(3)
N2 C4 1.483(3)
N3 C6 1.347(3)
C1 C2 1.479(4)
C2 C12 1.520(4)
C2 C3 1.543(4)
C2 C5 1.561(4)
C3 C4 1.538(4)
C4 C8 1.518(4)
C5 C15 1.510(3)
C6 C21 1.488(4)
C7 C24 1.500(4)
C9 C10 1.376(5)
C9 C14 1.385(5)
C10 C11 1.382(4)
C11 C12 1.397(4)
C12 C13 1.389(4)
C13 C14 1.375(4)
C15 C16 1.384(4)
C15 C20 1.395(4)
C16 C17 1.397(4)
C17 C18 1.388(4)
C18 C19 1.383(4)
C19 C20 1.381(4)
C21 C26 1.395(4)
C21 C22 1.399(4)
C22 C23 1.374(4)
C23 C24 1.393(4)
C24 C25 1.360(4)
C25 C26 1.393(4)
I101 C108 2.153(3)
F101 C107 1.340(4)
F102 C107 1.337(4)
F103 C107 1.320(5)
O101 C106 1.235(3)
N101 C101 1.138(4)
N102 N103 1.402(3)
N102 C105 1.469(3)
N102 C104 1.475(3)
N103 C106 1.340(3)
C101 C102 1.477(4)
C102 C112 1.527(4)
C102 C103 1.564(4)
C102 C105 1.566(3)
C103 C104 1.542(4)
C104 C108 1.522(4)
C105 C115 1.500(3)
C106 C121 1.509(4)
C107 C124 1.499(4)
C109 C110 1.376(5)
C109 C114 1.389(5)
C110 C111 1.397(4)
C111 C112 1.390(4)
C112 C113 1.386(4)
C113 C114 1.392(4)
C115 C116 1.388(4)
C115 C120 1.410(4)
C116 C117 1.408(4)
C117 C118 1.385(4)
C118 C119 1.369(4)
C119 C120 1.398(4)
C121 C126 1.379(4)
C121 C122 1.390(4)
C122 C123 1.392(4)
C123 C124 1.387(4)
C124 C125 1.380(4)
C125 C126 1.386(4)
I201 C208 2.156(4)
F201 C207 1.339(5)
F202 C207 1.290(4)
F203 C207 1.328(5)
O201 C206 1.228(3)
N201 C201 1.143(4)
N202 N203 1.390(3)
N202 C205 1.462(4)
N202 C204 1.476(4)
N203 C206 1.349(3)
C201 C202 1.478(4)
C202 C212 1.519(4)
C202 C205 1.562(4)
C202 C203 1.564(4)
C203 C204 1.533(4)
C204 C208 1.507(5)
C205 C215 1.517(4)
C206 C221 1.484(4)
C207 C224 1.508(4)
C209 C214 1.352(5)
C209 C210 1.366(5)
C210 C211 1.392(5)
C211 C212 1.390(4)
C212 C213 1.395(4)
C213 C214 1.404(5)
C215 C220 1.392(4)
C215 C216 1.397(4)
C216 C217 1.403(4)
C217 C218 1.372(5)
C218 C219 1.376(5)
C219 C220 1.388(4)
C221 C222 1.397(4)
C221 C226 1.404(4)
C222 C223 1.387(4)
C223 C224 1.380(4)
C224 C225 1.382(4)
C225 C226 1.385(4)
I301 C308 2.159(3)
F301 C307 1.318(5)
F302 C307 1.341(5)
F303 C307 1.319(4)
O301 C306 1.232(3)
N301 C301 1.144(4)
N302 N303 1.397(3)
N302 C305 1.459(3)
N302 C304 1.475(3)
N303 C306 1.356(3)
C301 C302 1.471(4)
C302 C312 1.524(4)
C302 C303 1.565(4)
C302 C305 1.571(4)
C303 C304 1.550(4)
C304 C308 1.502(4)
C305 C315 1.497(4)
C306 C321 1.504(4)
C307 C324 1.495(4)
C309 C314 1.372(5)
C309 C310 1.387(5)
C310 C311 1.376(4)
C311 C312 1.397(4)
C312 C313 1.390(4)
C313 C314 1.387(4)
C315 C316 1.390(4)
C315 C320 1.394(4)
C316 C317 1.399(4)
C317 C318 1.398(4)
C318 C319 1.383(5)
C319 C320 1.385(4)
C321 C322 1.389(4)
C321 C326 1.394(4)
C322 C323 1.385(4)
C323 C324 1.390(4)
C324 C325 1.385(4)
C325 C326 1.382(4)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.029 0.209 0.748 648.4 127.6
2 -0.064 0.709 0.252 648.4 127.8
|
1501966.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501966
loop_
_publ_author_name
'Turner, Penelope A.'
'Griffin, Ellanna M.'
'Whatmore, Jacqueline L.'
'Shipman, Michael'
_publ_section_title
;
Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond
construction and use in the identification of the
"antiausterity" pharmacophore of the kigamicins.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1056
_journal_page_last 1059
_journal_paper_doi 10.1021/ol103103n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C21 H18 O4'
_chemical_formula_weight 334.35
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 96.7267(17)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.2467(2)
_cell_length_b 7.47592(13)
_cell_length_c 17.7579(3)
_cell_measurement_reflns_used 7676
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 32.59
_cell_measurement_theta_min 2.72
_cell_volume 1614.64(5)
_computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)'
_computing_publication_material 'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type 'Oxford Diffraction Gemini R'
_diffrn_measurement_method '\f & \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0309
_diffrn_reflns_av_sigmaI/netI 0.0467
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 21519
_diffrn_reflns_theta_full 28.00
_diffrn_reflns_theta_max 32.65
_diffrn_reflns_theta_min 2.96
_diffrn_standards_decay_% nil
_exptl_absorpt_coefficient_mu 0.095
_exptl_absorpt_correction_T_max 1.00
_exptl_absorpt_correction_T_min 0.94
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.375
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 704
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.384
_refine_diff_density_min -0.257
_refine_diff_density_rms 0.050
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.926
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 5502
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.926
_refine_ls_R_factor_all 0.0692
_refine_ls_R_factor_gt 0.0429
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0624P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1019
_refine_ls_wR_factor_ref 0.1072
_reflns_number_gt 3704
_reflns_number_total 5502
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103103n_si_002.cif
_cod_data_source_block pt1
_cod_original_cell_volume 1614.63(5)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1501966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83144(9) 0.81412(15) -0.05164(5) 0.0204(2) Uani 0.561(3) 1 d P A 1
H1A H 0.8704 0.6990 -0.0552 0.025 Uiso 0.561(3) 1 calc PR A 1
H1B H 0.8708 0.9054 -0.0785 0.025 Uiso 0.561(3) 1 calc PR A 1
C2 C 0.71590(16) 0.7952(3) -0.09137(10) 0.0223(5) Uani 0.561(3) 1 d P A 1
H2A H 0.7175 0.7914 -0.1470 0.027 Uiso 0.561(3) 1 calc PR A 1
H2B H 0.6827 0.6825 -0.0756 0.027 Uiso 0.561(3) 1 calc PR A 1
C3 C 0.64860(17) 0.9524(3) -0.07073(10) 0.0241(5) Uani 0.561(3) 1 d P A 1
H3A H 0.5751 0.9483 -0.1006 0.029 Uiso 0.561(3) 1 calc PR A 1
H3B H 0.6850 1.0650 -0.0832 0.029 Uiso 0.561(3) 1 calc PR A 1
C4 C 0.63559(9) 0.94872(15) 0.01653(6) 0.0205(2) Uani 0.561(3) 1 d P A 1
H4A H 0.6033 1.0628 0.0316 0.025 Uiso 0.561(3) 1 calc PR A 1
H4B H 0.5859 0.8500 0.0275 0.025 Uiso 0.561(3) 1 calc PR A 1
C1A C 0.83144(9) 0.81412(15) -0.05164(5) 0.0204(2) Uani 0.439(3) 1 d P A 2
H1C H 0.8252 0.6825 -0.0566 0.025 Uiso 0.439(3) 1 calc PR A 2
H1D H 0.8996 0.8523 -0.0720 0.025 Uiso 0.439(3) 1 calc PR A 2
C2A C 0.7280(2) 0.9069(4) -0.09820(13) 0.0190(6) Uiso 0.439(3) 1 d P A 2
H2AA H 0.7389 1.0380 -0.0990 0.023 Uiso 0.439(3) 1 calc PR A 2
H2AB H 0.7195 0.8631 -0.1512 0.023 Uiso 0.439(3) 1 calc PR A 2
C3A C 0.6249(2) 0.8625(4) -0.06079(14) 0.0199(6) Uiso 0.439(3) 1 d P A 2
H3AA H 0.5587 0.9084 -0.0922 0.024 Uiso 0.439(3) 1 calc PR A 2
H3AB H 0.6174 0.7312 -0.0559 0.024 Uiso 0.439(3) 1 calc PR A 2
C4A C 0.63559(9) 0.94872(15) 0.01653(6) 0.0205(2) Uani 0.439(3) 1 d P A 2
H4C H 0.6212 1.0786 0.0105 0.025 Uiso 0.439(3) 1 calc PR A 2
H4D H 0.5790 0.8982 0.0459 0.025 Uiso 0.439(3) 1 calc PR A 2
O5 O 0.74407(6) 0.96342(9) 0.13536(4) 0.01638(15) Uani 1 1 d . A .
C5 C 0.74634(8) 0.92221(13) 0.06020(5) 0.0155(2) Uani 1 1 d . . .
C6 C 0.83652(8) 0.86653(13) 0.03075(5) 0.0153(2) Uani 1 1 d . A .
O7 O 1.02660(6) 0.80079(10) 0.05380(4) 0.01891(16) Uani 1 1 d . A .
C7 C 0.94188(8) 0.85430(13) 0.07790(5) 0.01461(19) Uani 1 1 d . . .
C8 C 0.93997(8) 0.90981(13) 0.15739(5) 0.01343(19) Uani 1 1 d . A .
C9 C 0.84046(8) 0.95420(13) 0.18310(5) 0.01437(19) Uani 1 1 d . . .
C10 C 0.83418(8) 0.99103(14) 0.25960(5) 0.0166(2) Uani 1 1 d . A .
H10A H 0.7656 1.0188 0.2768 0.020 Uiso 1 1 calc R . .
C11 C 0.92883(8) 0.98654(13) 0.30963(5) 0.0160(2) Uani 1 1 d . . .
H11A H 0.9248 1.0104 0.3618 0.019 Uiso 1 1 calc R A .
C12 C 1.03138(8) 0.94748(13) 0.28534(5) 0.01395(19) Uani 1 1 d . A .
C13 C 1.03519(8) 0.90943(13) 0.20912(5) 0.01430(19) Uani 1 1 d . . .
H13A H 1.1039 0.8826 0.1918 0.017 Uiso 1 1 calc R A .
C14 C 1.13340(8) 0.94776(13) 0.33982(5) 0.01473(19) Uani 1 1 d . . .
C15 C 1.13315(9) 0.88139(13) 0.41361(5) 0.0169(2) Uani 1 1 d . A .
H15A H 1.0671 0.8353 0.4292 0.020 Uiso 1 1 calc R . .
C16 C 1.22859(9) 0.88233(14) 0.46414(5) 0.0190(2) Uani 1 1 d . . .
H16A H 1.2272 0.8364 0.5139 0.023 Uiso 1 1 calc R A .
C17 C 1.32573(9) 0.94941(13) 0.44284(5) 0.0180(2) Uani 1 1 d . A .
H17A H 1.3909 0.9491 0.4776 0.022 Uiso 1 1 calc R . .
C18 C 1.32690(8) 1.01772(13) 0.36961(5) 0.0158(2) Uani 1 1 d . . .
C19 C 1.23132(8) 1.01580(13) 0.31864(5) 0.01502(19) Uani 1 1 d . A .
H19A H 1.2329 1.0614 0.2688 0.018 Uiso 1 1 calc R . .
O20 O 1.51739(6) 1.09776(12) 0.38997(4) 0.0294(2) Uani 1 1 d . . .
C20 C 1.43150(8) 1.09364(14) 0.34879(5) 0.0184(2) Uani 1 1 d . A .
O21 O 1.42143(6) 1.15723(10) 0.27731(4) 0.02136(17) Uani 1 1 d . . .
C22 C 1.52117(10) 1.22420(19) 0.25197(7) 0.0331(3) Uani 1 1 d . A .
H22A H 1.5044 1.2779 0.2016 0.050 Uiso 1 1 calc R . .
H22B H 1.5732 1.1255 0.2494 0.050 Uiso 1 1 calc R . .
H22C H 1.5537 1.3148 0.2877 0.050 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0177(5) 0.0299(6) 0.0135(4) -0.0011(4) 0.0011(4) -0.0034(4)
C2 0.0231(10) 0.0303(13) 0.0123(8) -0.0004(7) -0.0030(7) -0.0031(8)
C3 0.0231(10) 0.0288(12) 0.0178(9) 0.0025(8) -0.0087(8) 0.0023(9)
C4 0.0152(5) 0.0247(5) 0.0204(5) -0.0010(4) -0.0036(4) 0.0015(4)
C1A 0.0177(5) 0.0299(6) 0.0135(4) -0.0011(4) 0.0011(4) -0.0034(4)
C4A 0.0152(5) 0.0247(5) 0.0204(5) -0.0010(4) -0.0036(4) 0.0015(4)
O5 0.0126(3) 0.0218(4) 0.0139(3) -0.0022(3) -0.0017(3) 0.0012(3)
C5 0.0166(5) 0.0154(5) 0.0138(4) -0.0001(3) -0.0015(4) -0.0016(4)
C6 0.0157(5) 0.0168(5) 0.0131(4) 0.0013(4) -0.0002(4) -0.0029(4)
O7 0.0155(4) 0.0255(4) 0.0160(3) -0.0012(3) 0.0030(3) 0.0010(3)
C7 0.0150(5) 0.0151(5) 0.0136(4) 0.0009(3) 0.0013(4) -0.0018(4)
C8 0.0144(4) 0.0128(4) 0.0129(4) 0.0005(3) 0.0008(4) -0.0011(3)
C9 0.0127(4) 0.0142(4) 0.0155(4) 0.0002(3) -0.0015(4) -0.0009(4)
C10 0.0146(5) 0.0194(5) 0.0164(4) -0.0019(4) 0.0038(4) 0.0003(4)
C11 0.0185(5) 0.0175(5) 0.0121(4) -0.0012(3) 0.0017(4) -0.0016(4)
C12 0.0143(5) 0.0134(4) 0.0137(4) 0.0010(3) -0.0003(4) -0.0012(3)
C13 0.0129(4) 0.0152(5) 0.0148(4) 0.0010(3) 0.0014(4) -0.0006(4)
C14 0.0163(5) 0.0134(5) 0.0139(4) -0.0017(3) -0.0010(4) 0.0013(4)
C15 0.0180(5) 0.0172(5) 0.0155(4) 0.0006(4) 0.0017(4) -0.0003(4)
C16 0.0255(5) 0.0186(5) 0.0122(4) 0.0012(4) -0.0008(4) 0.0021(4)
C17 0.0187(5) 0.0179(5) 0.0156(4) -0.0015(4) -0.0047(4) 0.0030(4)
C18 0.0162(5) 0.0149(5) 0.0156(4) -0.0016(4) -0.0014(4) 0.0015(4)
C19 0.0170(5) 0.0152(5) 0.0124(4) 0.0002(3) -0.0005(4) 0.0013(4)
O20 0.0180(4) 0.0427(5) 0.0251(4) 0.0049(3) -0.0075(3) -0.0040(4)
C20 0.0177(5) 0.0189(5) 0.0176(4) 0.0000(4) -0.0022(4) 0.0008(4)
O21 0.0155(4) 0.0274(4) 0.0203(3) 0.0059(3) -0.0017(3) -0.0043(3)
C22 0.0218(6) 0.0433(8) 0.0335(6) 0.0111(5) -0.0001(5) -0.0130(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 114.00(11)
C6 C1 H1A 108.8
C2 C1 H1A 108.8
C6 C1 H1B 108.8
C2 C1 H1B 108.8
H1A C1 H1B 107.6
C3 C2 C1 108.82(16)
C3 C2 H2A 109.9
C1 C2 H2A 109.9
C3 C2 H2B 109.9
C1 C2 H2B 109.9
H2A C2 H2B 108.3
C2 C3 C4 110.31(15)
C2 C3 H3A 109.6
C4 C3 H3A 109.6
C2 C3 H3B 109.6
C4 C3 H3B 109.6
H3A C3 H3B 108.1
C5 C4 C3 108.80(11)
C5 C4 H4A 109.9
C3 C4 H4A 109.9
C5 C4 H4B 109.9
C3 C4 H4B 109.9
H4A C4 H4B 108.3
C3A C2A H2AA 109.9
C3A C2A H2AB 109.9
H2AA C2A H2AB 108.3
C2A C3A H3AA 110.0
C2A C3A H3AB 110.0
H3AA C3A H3AB 108.4
C9 O5 C5 118.39(8)
C6 C5 O5 124.02(8)
C6 C5 C4 125.24(8)
O5 C5 C4 110.74(8)
C5 C6 C7 120.63(8)
C5 C6 C1 121.06(8)
C7 C6 C1 118.31(8)
O7 C7 C6 123.04(8)
O7 C7 C8 122.10(8)
C6 C7 C8 114.86(8)
C9 C8 C13 118.71(8)
C9 C8 C7 119.63(8)
C13 C8 C7 121.55(9)
O5 C9 C8 122.18(8)
O5 C9 C10 116.72(9)
C8 C9 C10 121.10(8)
C11 C10 C9 119.02(9)
C11 C10 H10A 120.5
C9 C10 H10A 120.5
C10 C11 C12 121.49(8)
C10 C11 H11A 119.3
C12 C11 H11A 119.3
C13 C12 C11 118.35(8)
C13 C12 C14 120.81(9)
C11 C12 C14 120.84(8)
C12 C13 C8 121.29(9)
C12 C13 H13A 119.4
C8 C13 H13A 119.4
C19 C14 C15 118.52(8)
C19 C14 C12 120.56(8)
C15 C14 C12 120.91(9)
C16 C15 C14 120.59(10)
C16 C15 H15A 119.7
C14 C15 H15A 119.7
C17 C16 C15 120.73(9)
C17 C16 H16A 119.6
C15 C16 H16A 119.6
C16 C17 C18 119.28(9)
C16 C17 H17A 120.4
C18 C17 H17A 120.4
C19 C18 C17 120.06(9)
C19 C18 C20 121.68(9)
C17 C18 C20 118.25(8)
C18 C19 C14 120.81(9)
C18 C19 H19A 119.6
C14 C19 H19A 119.6
O20 C20 O21 122.54(10)
O20 C20 C18 124.98(9)
O21 C20 C18 112.48(8)
C20 O21 C22 115.44(8)
O21 C22 H22A 109.5
O21 C22 H22B 109.5
H22A C22 H22B 109.5
O21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.5089(13)
C1 C2 1.512(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.505(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.576(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.4947(14)
C4 H4A 0.9900
C4 H4B 0.9900
C2A C3A 1.531(4)
C2A H2AA 0.9900
C2A H2AB 0.9900
C3A H3AA 0.9900
C3A H3AB 0.9900
O5 C9 1.3720(11)
O5 C5 1.3732(11)
C5 C6 1.3423(14)
C6 C7 1.4565(13)
O7 C7 1.2343(11)
C7 C8 1.4741(12)
C8 C9 1.3908(14)
C8 C13 1.3975(13)
C9 C10 1.3969(13)
C10 C11 1.3758(14)
C10 H10A 0.9500
C11 C12 1.4056(13)
C11 H11A 0.9500
C12 C13 1.3891(12)
C12 C14 1.4879(13)
C13 H13A 0.9500
C14 C19 1.3942(14)
C14 C15 1.4016(13)
C15 C16 1.3877(14)
C15 H15A 0.9500
C16 C17 1.3839(15)
C16 H16A 0.9500
C17 C18 1.3988(13)
C17 H17A 0.9500
C18 C19 1.3933(13)
C18 C20 1.4869(15)
C19 H19A 0.9500
O20 C20 1.2091(12)
C20 O21 1.3475(12)
O21 C22 1.4401(13)
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
|
1501967.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501967.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501967
loop_
_publ_author_name
'Cohen, Daniel T.'
'Cardinal-David, Benoit'
'Roberts, John M.'
'Sarjeant, Amy A.'
'Scheidt, Karl A.'
_publ_section_title
;
NHC-catalyzed/titanium(IV)-mediated highly diastereo- and
enantioselective dimerization of enals.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1068
_journal_page_last 1071
_journal_paper_doi 10.1021/ol103112v
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C26 H27 N O2'
_chemical_formula_weight 385.49
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_audit_update_record
;
2010-03-01 # Formatted by publCIF
;
_cell_angle_alpha 90.00
_cell_angle_beta 110.214(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 13.1938(7)
_cell_length_b 6.3948(3)
_cell_length_c 13.5567(7)
_cell_measurement_reflns_used 2558
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 62.59
_cell_measurement_theta_min 3.47
_cell_volume 1073.35(10)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0375
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 10043
_diffrn_reflns_theta_full 66.26
_diffrn_reflns_theta_max 66.26
_diffrn_reflns_theta_min 3.47
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.584
_exptl_absorpt_correction_T_max 0.9455
_exptl_absorpt_correction_T_min 0.7541
_exptl_absorpt_correction_type numerical
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.193
_exptl_crystal_density_meas 0
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 412
_exptl_crystal_size_max 0.51
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.258
_refine_diff_density_min -0.161
_refine_diff_density_rms 0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.3(3)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 265
_refine_ls_number_reflns 10043
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.046
_refine_ls_R_factor_all 0.0602
_refine_ls_R_factor_gt 0.0521
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1453
_refine_ls_wR_factor_ref 0.1510
_reflns_number_gt 8603
_reflns_number_total 10043
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103112v_si_002.cif
_cod_data_source_block n0228_0m
_cod_original_cell_volume 1073.35(9)
_cod_original_sg_symbol_H-M 'P 21'
_cod_database_code 1501967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 0.39500(10) 0.3501(2) 0.39326(10) 0.0436(3) Uani 1 1 d .
O2 O 0.30808(12) 0.6472(2) 0.33605(11) 0.0520(4) Uani 1 1 d .
N1 N 0.40271(12) -0.0407(3) 0.47777(12) 0.0394(4) Uani 1 1 d .
H1A H 0.4738 -0.0678 0.5132 0.059 Uiso 1 1 calc R
H1B H 0.3965 0.0796 0.4403 0.059 Uiso 1 1 calc R
H1C H 0.3732 -0.1484 0.4332 0.059 Uiso 1 1 calc R
C1 C 0.32173(14) 0.4575(3) 0.32931(13) 0.0335(4) Uani 1 1 d .
C2 C 0.37054(16) 0.1126(4) 0.17859(14) 0.0403(5) Uani 1 1 d .
C3 C 0.26648(16) 0.1303(4) 0.20246(15) 0.0428(5) Uani 1 1 d .
H3 H 0.2708 0.0264 0.2589 0.051 Uiso 1 1 calc R
C4 C 0.40926(17) 0.2798(4) 0.13850(15) 0.0479(6) Uani 1 1 d .
H4 H 0.3727 0.4103 0.1293 0.057 Uiso 1 1 calc R
C5 C 0.42616(17) -0.0754(4) 0.19277(15) 0.0451(5) Uani 1 1 d .
H5 H 0.4009 -0.1916 0.2214 0.054 Uiso 1 1 calc R
C6 C 0.24126(16) 0.3403(4) 0.23950(15) 0.0421(5) Uani 1 1 d .
C7 C 0.16040(16) 0.0801(4) 0.10604(16) 0.0481(5) Uani 1 1 d .
H7 H 0.1400 -0.0687 0.1121 0.058 Uiso 1 1 calc R
C8 C 0.2324(2) 0.0663(5) 0.49914(19) 0.0603(7) Uani 1 1 d .
C9 C 0.13649(17) 0.3869(4) 0.19614(17) 0.0516(6) Uani 1 1 d .
H9 H 0.1051 0.5123 0.2099 0.062 Uiso 1 1 calc R
C10 C 0.51632(18) -0.0965(4) 0.16636(18) 0.0544(6) Uani 1 1 d .
H10 H 0.5530 -0.2269 0.1767 0.065 Uiso 1 1 calc R
C11 C 0.20278(18) -0.0529(5) -0.04876(17) 0.0535(6) Uani 1 1 d .
H11 H 0.2148 -0.1864 -0.0160 0.064 Uiso 1 1 calc R
C12 C 0.50186(19) 0.2602(4) 0.11108(16) 0.0554(6) Uani 1 1 d .
H12 H 0.5283 0.3761 0.0834 0.066 Uiso 1 1 calc R
C13 C 0.17292(15) 0.1079(4) 0.00020(15) 0.0438(5) Uani 1 1 d .
C14 C 0.34472(19) -0.0173(4) 0.55426(16) 0.0524(6) Uani 1 1 d .
H14 H 0.3850 0.0870 0.6087 0.063 Uiso 1 1 calc R
C15 C 0.55462(18) 0.0681(5) 0.12508(18) 0.0580(7) Uani 1 1 d .
H15 H 0.6170 0.0514 0.1060 0.070 Uiso 1 1 calc R
C16 C 0.2013(2) 0.1704(7) -0.1916(2) 0.0803(10) Uani 1 1 d .
H16 H 0.2106 0.1916 -0.2573 0.096 Uiso 1 1 calc R
C17 C 0.0539(3) 0.0259(11) 0.3732(3) 0.130(2) Uani 1 1 d .
H17A H 0.0029 -0.0765 0.3848 0.156 Uiso 1 1 calc R
H17B H 0.0405 0.0289 0.2967 0.156 Uiso 1 1 calc R
C18 C 0.07469(18) 0.2205(5) 0.12410(19) 0.0624(7) Uani 1 1 d .
H18A H 0.0269 0.2812 0.0570 0.075 Uiso 1 1 calc R
H18B H 0.0300 0.1405 0.1565 0.075 Uiso 1 1 calc R
C19 C 0.2166(2) -0.0287(5) -0.14651(19) 0.0669(7) Uani 1 1 d .
H19 H 0.2358 -0.1439 -0.1807 0.080 Uiso 1 1 calc R
C20 C 0.2039(4) 0.2626(6) 0.5243(3) 0.1004(12) Uani 1 1 d .
H20 H 0.2548 0.3444 0.5769 0.120 Uiso 1 1 calc R
C21 C 0.3474(2) -0.2251(5) 0.60859(19) 0.0701(8) Uani 1 1 d .
H21A H 0.3141 -0.3329 0.5559 0.105 Uiso 1 1 calc R
H21B H 0.3073 -0.2135 0.6572 0.105 Uiso 1 1 calc R
H21C H 0.4224 -0.2636 0.6478 0.105 Uiso 1 1 calc R
C22 C 0.15815(19) 0.3054(4) -0.04736(18) 0.0609(7) Uani 1 1 d .
H22 H 0.1377 0.4197 -0.0136 0.073 Uiso 1 1 calc R
C23 C 0.1572(2) -0.0501(7) 0.4224(2) 0.0782(9) Uani 1 1 d .
H23 H 0.1766 -0.1832 0.4033 0.094 Uiso 1 1 calc R
C24 C 0.1726(2) 0.3370(6) -0.1416(2) 0.0763(8) Uani 1 1 d .
H24 H 0.1631 0.4724 -0.1723 0.092 Uiso 1 1 calc R
C25 C 0.0276(5) 0.2207(17) 0.4015(7) 0.197(5) Uani 1 1 d .
H25 H -0.0438 0.2727 0.3701 0.237 Uiso 1 1 calc R
C26 C 0.1027(7) 0.3377(10) 0.4735(7) 0.183(4) Uani 1 1 d .
H26 H 0.0846 0.4746 0.4889 0.220 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0406(7) 0.0357(8) 0.0443(7) 0.0004(6) 0.0014(6) 0.0006(6)
O2 0.0685(10) 0.0333(10) 0.0448(8) -0.0034(6) 0.0076(7) 0.0015(7)
N1 0.0402(8) 0.0318(9) 0.0371(8) 0.0005(7) 0.0019(6) 0.0008(7)
C1 0.0372(10) 0.0299(12) 0.0362(10) 0.0010(8) 0.0162(8) 0.0009(8)
C2 0.0407(10) 0.0451(14) 0.0284(9) -0.0099(8) 0.0034(8) -0.0082(9)
C3 0.0407(10) 0.0466(13) 0.0359(9) -0.0044(9) 0.0068(8) 0.0017(9)
C4 0.0454(11) 0.0495(15) 0.0378(11) -0.0013(10) 0.0004(9) 0.0021(10)
C5 0.0498(12) 0.0390(14) 0.0414(11) -0.0077(9) 0.0094(9) -0.0039(9)
C6 0.0426(11) 0.0371(13) 0.0409(10) -0.0025(9) 0.0072(8) 0.0028(9)
C7 0.0458(11) 0.0518(15) 0.0431(11) -0.0060(9) 0.0108(9) -0.0120(10)
C8 0.0715(15) 0.0672(19) 0.0537(13) 0.0104(12) 0.0362(13) 0.0190(14)
C9 0.0415(11) 0.0575(15) 0.0549(13) -0.0084(11) 0.0156(10) 0.0061(10)
C10 0.0481(12) 0.0491(16) 0.0589(14) -0.0161(11) 0.0095(11) 0.0059(10)
C11 0.0500(12) 0.0606(16) 0.0449(12) -0.0068(11) 0.0101(10) -0.0022(11)
C12 0.0581(14) 0.0624(17) 0.0398(11) -0.0014(11) 0.0093(10) -0.0087(12)
C13 0.0336(10) 0.0510(14) 0.0401(10) -0.0047(10) 0.0043(8) -0.0064(9)
C14 0.0623(13) 0.0542(16) 0.0365(10) -0.0056(10) 0.0115(9) -0.0041(11)
C15 0.0453(12) 0.083(2) 0.0467(12) -0.0234(12) 0.0171(10) -0.0070(13)
C16 0.0628(16) 0.128(3) 0.0492(14) 0.0215(18) 0.0188(13) -0.0024(17)
C17 0.0544(18) 0.244(7) 0.099(2) 0.068(3) 0.0352(17) 0.038(3)
C18 0.0452(12) 0.085(2) 0.0548(14) -0.0137(13) 0.0148(10) -0.0035(12)
C19 0.0556(14) 0.091(2) 0.0554(14) -0.0159(16) 0.0203(11) 0.0018(14)
C20 0.148(3) 0.074(2) 0.126(3) 0.030(2) 0.107(3) 0.036(2)
C21 0.0669(15) 0.084(2) 0.0530(13) 0.0221(14) 0.0122(11) -0.0007(14)
C22 0.0566(13) 0.066(2) 0.0508(13) 0.0041(12) 0.0065(10) 0.0000(12)
C23 0.0468(14) 0.126(3) 0.0626(15) 0.0089(18) 0.0197(12) 0.0146(16)
C24 0.0699(16) 0.088(2) 0.0625(16) 0.0186(16) 0.0126(13) -0.0004(16)
C25 0.109(4) 0.281(11) 0.258(8) 0.205(8) 0.135(5) 0.129(6)
C26 0.244(7) 0.131(5) 0.288(9) 0.131(6) 0.235(8) 0.136(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O3 125.94(17)
O2 C1 C6 118.11(16)
O3 C1 C6 115.90(18)
C4 C2 C5 118.7(2)
C4 C2 C3 120.6(2)
C5 C2 C3 120.6(2)
C6 C3 C2 117.3(2)
C6 C3 C7 102.75(18)
C2 C3 C7 114.41(17)
C6 C3 H3 107.3
C2 C3 H3 107.3
C7 C3 H3 107.3
C2 C4 C12 120.5(2)
C2 C4 H4 119.7
C12 C4 H4 119.7
C10 C5 C2 121.1(2)
C10 C5 H5 119.5
C2 C5 H5 119.5
C9 C6 C3 111.78(19)
C9 C6 C1 124.76(19)
C3 C6 C1 122.63(16)
C13 C7 C18 114.5(2)
C13 C7 C3 114.00(17)
C18 C7 C3 103.77(19)
C13 C7 H7 108.1
C18 C7 H7 108.1
C3 C7 H7 108.1
C6 C9 C18 112.1(2)
C6 C9 H9 124.0
C18 C9 H9 124.0
C5 C10 C15 120.5(2)
C5 C10 H10 119.8
C15 C10 H10 119.8
C13 C11 C19 122.0(3)
C13 C11 H11 119.0
C19 C11 H11 119.0
C15 C12 C4 119.5(2)
C15 C12 H12 120.2
C4 C12 H12 120.2
C11 C13 C22 118.6(2)
C11 C13 C7 121.4(3)
C22 C13 C7 120.0(2)
C10 C15 C12 119.6(2)
C10 C15 H15 120.2
C12 C15 H15 120.2
C19 C16 C24 120.9(3)
C19 C16 H16 119.6
C24 C16 H16 119.6
C9 C18 C7 104.98(18)
C9 C18 H18A 110.8
C7 C18 H18A 110.8
C9 C18 H18B 110.8
C7 C18 H18B 110.8
H18A C18 H18B 108.8
C16 C19 C11 118.0(3)
C16 C19 H19 121.0
C11 C19 H19 121.0
C24 C22 C13 121.7(3)
C24 C22 H22 119.1
C13 C22 H22 119.1
C22 C24 C16 118.7(3)
C22 C24 H24 120.6
C16 C24 H24 120.6
C14 N1 H1A 109.4
C14 N1 H1B 109.7
H1A N1 H1B 109.5
C14 N1 H1C 109.4
H1A N1 H1C 109.4
H1B N1 H1C 109.5
C23 C8 C20 119.7(3)
C23 C8 C14 120.1(3)
C20 C8 C14 120.1(3)
N1 C14 C21 109.3(2)
N1 C14 C8 110.13(17)
C21 C14 C8 113.8(2)
N1 C14 H14 107.8
C21 C14 H14 107.8
C8 C14 H14 107.8
C23 C17 C25 117.2(6)
C23 C17 H17A 108.0
C25 C17 H17A 108.0
C23 C17 H17B 108.0
C25 C17 H17B 108.0
H17A C17 H17B 107.2
C26 C20 C8 120.5(6)
C26 C20 H20 119.8
C8 C20 H20 119.8
C14 C21 H21A 109.5
C14 C21 H21B 109.5
H21A C21 H21B 109.5
C14 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C8 C23 C17 120.1(5)
C8 C23 H23 119.9
C17 C23 H23 119.9
C26 C25 C17 121.3(4)
C26 C25 H25 119.3
C17 C25 H25 119.3
C25 C26 C20 121.0(7)
C25 C26 H26 119.5
C20 C26 H26 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.232(3)
O3 C1 1.257(2)
C1 C6 1.514(3)
C2 C4 1.378(3)
C2 C5 1.386(3)
C2 C3 1.520(3)
C3 C6 1.507(4)
C3 C7 1.584(3)
C3 H3 1.0000
C4 C12 1.397(4)
C4 H4 0.9500
C5 C10 1.364(4)
C5 H5 0.9500
C6 C9 1.334(3)
C7 C13 1.509(3)
C7 C18 1.530(4)
C7 H7 1.0000
C9 C18 1.484(4)
C9 H9 0.9500
C10 C15 1.381(4)
C10 H10 0.9500
C11 C13 1.360(4)
C11 C19 1.398(4)
C11 H11 0.9500
C12 C15 1.382(4)
C12 H12 0.9500
C13 C22 1.406(4)
C15 H15 0.9500
C16 C19 1.397(6)
C16 C24 1.403(6)
C16 H16 0.9500
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19 0.9500
C22 C24 1.362(4)
C22 H22 0.9500
C24 H24 0.9500
N1 C14 1.484(3)
N1 H1A 0.9106
N1 H1B 0.9098
N1 H1C 0.9102
C8 C23 1.381(5)
C8 C20 1.392(5)
C8 C14 1.519(4)
C14 C21 1.504(4)
C14 H14 1.0000
C17 C23 1.388(5)
C17 C25 1.428(13)
C17 H17A 0.9900
C17 H17B 0.9900
C20 C26 1.342(9)
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C23 H23 0.9500
C25 C26 1.333(14)
C25 H25 0.9500
C26 H26 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 C2 C3 C6 -33.4(2)
C5 C2 C3 C6 149.30(19)
C4 C2 C3 C7 87.1(3)
C5 C2 C3 C7 -90.2(3)
C5 C2 C4 C12 0.8(3)
C3 C2 C4 C12 -176.55(18)
C4 C2 C5 C10 -0.9(3)
C3 C2 C5 C10 176.51(17)
C2 C3 C6 C9 139.1(2)
C7 C3 C6 C9 12.7(3)
C2 C3 C6 C1 -50.9(3)
C7 C3 C6 C1 -177.35(19)
O2 C1 C6 C9 -31.3(3)
O3 C1 C6 C9 146.3(2)
O2 C1 C6 C3 160.1(2)
O3 C1 C6 C3 -22.4(3)
C6 C3 C7 C13 105.1(2)
C2 C3 C7 C13 -23.1(3)
C6 C3 C7 C18 -20.1(3)
C2 C3 C7 C18 -148.3(2)
C3 C6 C9 C18 0.5(3)
C1 C6 C9 C18 -169.2(2)
C2 C5 C10 C15 -0.2(3)
C2 C4 C12 C15 0.3(3)
C19 C11 C13 C22 -1.5(3)
C19 C11 C13 C7 -178.75(19)
C18 C7 C13 C11 -149.1(2)
C3 C7 C13 C11 91.7(3)
C18 C7 C13 C22 33.7(3)
C3 C7 C13 C22 -85.5(3)
C5 C10 C15 C12 1.4(3)
C4 C12 C15 C10 -1.4(3)
C6 C9 C18 C7 -14.1(3)
C13 C7 C18 C9 -104.2(2)
C3 C7 C18 C9 20.7(3)
C24 C16 C19 C11 0.1(4)
C13 C11 C19 C16 1.3(3)
C11 C13 C22 C24 0.3(3)
C7 C13 C22 C24 177.6(2)
C13 C22 C24 C16 1.0(4)
C19 C16 C24 C22 -1.2(4)
C23 C8 C14 N1 65.0(3)
C20 C8 C14 N1 -114.1(3)
C23 C8 C14 C21 -58.1(3)
C20 C8 C14 C21 122.7(3)
C23 C8 C20 C26 0.2(5)
C14 C8 C20 C26 179.4(3)
C20 C8 C23 C17 -1.6(4)
C14 C8 C23 C17 179.2(3)
C25 C17 C23 C8 0.5(6)
C23 C17 C25 C26 2.0(8)
C17 C25 C26 C20 -3.5(10)
C8 C20 C26 C25 2.3(8)
|
1501968.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501968.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501968
loop_
_publ_author_name
'Cohen, Daniel T.'
'Cardinal-David, Benoit'
'Roberts, John M.'
'Sarjeant, Amy A.'
'Scheidt, Karl A.'
_publ_section_title
;
NHC-catalyzed/titanium(IV)-mediated highly diastereo- and
enantioselective dimerization of enals.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1068
_journal_page_last 1071
_journal_paper_doi 10.1021/ol103112v
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C25 H27 N O2'
_chemical_formula_weight 373.48
_chemical_name_systematic ?
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 116.08(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 28.765(6)
_cell_length_b 6.1340(12)
_cell_length_c 25.888(5)
_cell_measurement_reflns_used 14675
_cell_measurement_temperature 293(2)
_cell_volume 4102.7(18)
_computing_cell_refinement HKL2000
_computing_data_collection 'MD-2 diffractometer software from EMBL'
_computing_data_reduction HKL2000
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type 'MAR 300 CCD'
_diffrn_measurement_method '\f scans'
_diffrn_radiation_monochromator Si(111)
_diffrn_radiation_source synchrotron
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.69996
_diffrn_reflns_av_R_equivalents 0.0475
_diffrn_reflns_av_sigmaI/netI 0.0506
_diffrn_reflns_limit_h_max 37
_diffrn_reflns_limit_h_min -38
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 32
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_number 8835
_diffrn_reflns_theta_full 28.74
_diffrn_reflns_theta_max 28.74
_diffrn_reflns_theta_min 3.99
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.076
_exptl_absorpt_correction_type none
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_density_diffrn 1.209
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1600
_refine_diff_density_max 0.358
_refine_diff_density_min -0.259
_refine_diff_density_rms 0.049
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.073
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 254
_refine_ls_number_reflns 4968
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.073
_refine_ls_R_factor_all 0.0798
_refine_ls_R_factor_gt 0.0643
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0898P)^2^+2.8600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1730
_refine_ls_wR_factor_ref 0.1844
_reflns_number_gt 3881
_reflns_number_total 4968
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103112v_si_003.cif
_cod_data_source_block n0305
_cod_original_cell_volume 4102.8(14)
_cod_original_sg_symbol_H-M 'C 2/c'
_cod_database_code 1501968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O 0.18261(4) 0.58136(19) 0.48193(5) 0.0361(3) Uani 1 1 d .
O1 O 0.17754(5) 0.27215(19) 0.52335(6) 0.0428(3) Uani 1 1 d .
N1 N 0.21101(5) -0.0034(2) 0.46700(6) 0.0323(3) Uani 1 1 d .
H1A H 0.2005 0.1016 0.4832 0.048 Uiso 1 1 calc R
H1B H 0.2454 -0.0107 0.4842 0.048 Uiso 1 1 calc R
H1C H 0.1979 -0.1304 0.4708 0.048 Uiso 1 1 calc R
C1 C 0.14705(6) 0.7812(3) 0.56363(8) 0.0328(4) Uani 1 1 d .
H1 H 0.1534 0.8802 0.5377 0.039 Uiso 1 1 calc R
C2 C 0.19690(6) 0.7720(3) 0.61843(7) 0.0326(4) Uani 1 1 d .
C3 C 0.12794(6) 0.5672(3) 0.53079(8) 0.0342(4) Uani 1 1 d .
H3 H 0.1219 0.4622 0.5557 0.041 Uiso 1 1 calc R
C4 C 0.21182(6) 0.5906(3) 0.65490(8) 0.0363(4) Uani 1 1 d .
H4 H 0.1899 0.4705 0.6463 0.044 Uiso 1 1 calc R
C5 C 0.16516(6) 0.4674(3) 0.51023(7) 0.0323(4) Uani 1 1 d .
C6 C 0.13466(6) 0.0316(3) 0.37441(8) 0.0347(4) Uani 1 1 d .
C7 C 0.29181(6) 0.7669(3) 0.71717(8) 0.0371(4) Uani 1 1 d .
H7 H 0.3234 0.7656 0.7497 0.044 Uiso 1 1 calc R
C8 C 0.19297(6) 0.0456(3) 0.40488(8) 0.0389(4) Uani 1 1 d .
H8A H 0.2079 -0.0580 0.3881 0.047 Uiso 1 1 calc R
H8B H 0.2041 0.1907 0.4004 0.047 Uiso 1 1 calc R
C9 C 0.27730(7) 0.9465(3) 0.68197(8) 0.0407(4) Uani 1 1 d .
H9 H 0.2991 1.0670 0.6910 0.049 Uiso 1 1 calc R
C10 C 0.09744(6) 0.8690(3) 0.56754(8) 0.0369(4) Uani 1 1 d .
H10 H 0.1003 1.0274 0.5730 0.044 Uiso 1 1 calc R
C11 C 0.11055(7) -0.1607(3) 0.34786(8) 0.0385(4) Uani 1 1 d .
H11 H 0.1304 -0.2786 0.3467 0.046 Uiso 1 1 calc R
C12 C 0.07553(6) 0.6333(3) 0.48181(8) 0.0422(4) Uani 1 1 d .
H12A H 0.0518 0.5108 0.4701 0.051 Uiso 1 1 calc R
H12B H 0.0799 0.6849 0.4488 0.051 Uiso 1 1 calc R
C13 C 0.09006(6) 0.7652(3) 0.61673(8) 0.0379(4) Uani 1 1 d .
C14 C 0.10478(7) 0.2075(3) 0.37539(9) 0.0431(4) Uani 1 1 d .
H14 H 0.1206 0.3376 0.3926 0.052 Uiso 1 1 calc R
C15 C 0.25935(6) 0.5878(3) 0.70418(8) 0.0371(4) Uani 1 1 d .
H15 H 0.2690 0.4661 0.7280 0.045 Uiso 1 1 calc R
C16 C 0.23036(7) 0.9492(3) 0.63310(8) 0.0370(4) Uani 1 1 d .
H16 H 0.2211 1.0721 0.6097 0.044 Uiso 1 1 calc R
C17 C 0.06567(7) 0.5668(3) 0.61222(10) 0.0464(5) Uani 1 1 d .
H17 H 0.0512 0.4947 0.5770 0.056 Uiso 1 1 calc R
C18 C 0.10975(7) 0.8702(3) 0.66958(9) 0.0438(4) Uani 1 1 d .
H18 H 0.1261 1.0041 0.6733 0.053 Uiso 1 1 calc R
C19 C 0.05126(8) 0.1897(4) 0.35073(9) 0.0502(5) Uani 1 1 d .
H19 H 0.0313 0.3077 0.3516 0.060 Uiso 1 1 calc R
C20 C 0.02753(7) -0.0030(4) 0.32485(9) 0.0471(5) Uani 1 1 d .
H20 H -0.0083 -0.0151 0.3086 0.057 Uiso 1 1 calc R
C21 C 0.05512(7) 0.8182(3) 0.50713(9) 0.0439(4) Uani 1 1 d .
H21A H 0.0474 0.9469 0.4830 0.053 Uiso 1 1 calc R
H21B H 0.0237 0.7722 0.5091 0.053 Uiso 1 1 calc R
C22 C 0.05720(7) -0.1780(3) 0.32313(9) 0.0436(4) Uani 1 1 d .
H22 H 0.0413 -0.3072 0.3053 0.052 Uiso 1 1 calc R
C23 C 0.06242(8) 0.4743(4) 0.65901(12) 0.0566(6) Uani 1 1 d .
H23 H 0.0468 0.3388 0.6552 0.068 Uiso 1 1 calc R
C25 C 0.10604(8) 0.7840(5) 0.71681(10) 0.0578(6) Uani 1 1 d .
H25 H 0.1191 0.8596 0.7515 0.069 Uiso 1 1 calc R
C24 C 0.08217(9) 0.5803(5) 0.71168(12) 0.0683(8) Uani 1 1 d .
H24 H 0.0796 0.5175 0.7430 0.082 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0275(5) 0.0329(6) 0.0461(7) 0.0010(5) 0.0146(5) 0.0000(4)
O1 0.0524(7) 0.0309(6) 0.0520(8) 0.0032(5) 0.0293(6) 0.0094(5)
N1 0.0253(6) 0.0295(6) 0.0413(8) -0.0009(6) 0.0140(6) 0.0011(5)
C1 0.0291(7) 0.0288(7) 0.0398(9) 0.0008(6) 0.0146(7) 0.0024(6)
C2 0.0281(7) 0.0332(8) 0.0384(9) -0.0014(6) 0.0162(7) 0.0045(6)
C3 0.0259(7) 0.0332(8) 0.0417(9) -0.0027(7) 0.0133(7) 0.0006(6)
C4 0.0312(8) 0.0347(8) 0.0457(10) -0.0019(7) 0.0194(7) -0.0027(6)
C5 0.0249(7) 0.0288(7) 0.0396(9) -0.0039(6) 0.0110(6) 0.0009(6)
C6 0.0301(7) 0.0382(8) 0.0358(9) 0.0025(7) 0.0143(6) 0.0019(6)
C7 0.0295(7) 0.0418(9) 0.0364(9) -0.0021(7) 0.0112(7) 0.0021(7)
C8 0.0318(8) 0.0444(9) 0.0423(10) 0.0018(7) 0.0179(7) -0.0005(7)
C9 0.0360(8) 0.0352(8) 0.0455(11) -0.0031(7) 0.0132(7) -0.0031(7)
C10 0.0322(8) 0.0326(8) 0.0449(10) -0.0007(7) 0.0161(7) 0.0058(6)
C11 0.0350(8) 0.0373(8) 0.0420(10) -0.0012(7) 0.0158(7) 0.0039(7)
C12 0.0272(8) 0.0509(10) 0.0433(10) -0.0065(8) 0.0107(7) 0.0052(7)
C13 0.0242(7) 0.0423(9) 0.0452(10) -0.0020(7) 0.0135(7) 0.0083(6)
C14 0.0411(9) 0.0366(9) 0.0460(11) -0.0025(8) 0.0139(8) 0.0042(7)
C15 0.0337(8) 0.0362(8) 0.0436(10) 0.0050(7) 0.0188(7) 0.0057(6)
C16 0.0351(8) 0.0307(8) 0.0430(10) -0.0003(7) 0.0152(7) 0.0009(6)
C17 0.0342(9) 0.0477(10) 0.0631(13) 0.0029(9) 0.0267(9) 0.0056(8)
C18 0.0333(8) 0.0509(11) 0.0462(11) -0.0015(8) 0.0165(8) 0.0095(7)
C19 0.0400(10) 0.0497(11) 0.0540(12) -0.0013(9) 0.0144(9) 0.0153(8)
C20 0.0286(8) 0.0573(12) 0.0492(11) 0.0028(9) 0.0113(7) 0.0039(8)
C21 0.0324(8) 0.0490(10) 0.0474(11) -0.0016(8) 0.0149(8) 0.0104(7)
C22 0.0357(9) 0.0408(9) 0.0466(11) -0.0022(8) 0.0110(8) -0.0026(7)
C23 0.0422(10) 0.0524(12) 0.0859(18) 0.0189(11) 0.0380(11) 0.0119(9)
C25 0.0372(10) 0.0923(18) 0.0428(12) 0.0068(11) 0.0166(8) 0.0182(11)
C24 0.0440(11) 0.105(2) 0.0654(16) 0.0406(15) 0.0329(11) 0.0341(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 H1A 109.5
C8 N1 H1B 109.5
H1A N1 H1B 109.5
C8 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C2 C1 C3 116.78(13)
C2 C1 C10 117.82(15)
C3 C1 C10 102.45(13)
C2 C1 H1 106.3
C3 C1 H1 106.3
C10 C1 H1 106.3
C16 C2 C4 117.88(16)
C16 C2 C1 118.98(15)
C4 C2 C1 123.13(15)
C5 C3 C1 113.86(13)
C5 C3 C12 113.83(15)
C1 C3 C12 102.39(13)
C5 C3 H3 108.8
C1 C3 H3 108.8
C12 C3 H3 108.8
C2 C4 C15 120.75(16)
C2 C4 H4 119.6
C15 C4 H4 119.6
O1 C5 O2 123.17(15)
O1 C5 C3 116.77(15)
O2 C5 C3 120.05(14)
C14 C6 C11 119.46(16)
C14 C6 C8 120.09(16)
C11 C6 C8 120.37(15)
C9 C7 C15 120.00(16)
C9 C7 H7 120.0
C15 C7 H7 120.0
N1 C8 C6 109.43(14)
N1 C8 H8A 109.8
C6 C8 H8A 109.8
N1 C8 H8B 109.8
C6 C8 H8B 109.8
H8A C8 H8B 108.2
C7 C9 C16 120.37(16)
C7 C9 H9 119.8
C16 C9 H9 119.8
C13 C10 C21 115.38(15)
C13 C10 C1 112.09(14)
C21 C10 C1 101.60(14)
C13 C10 H10 109.2
C21 C10 H10 109.2
C1 C10 H10 109.2
C22 C11 C6 120.38(16)
C22 C11 H11 119.8
C6 C11 H11 119.8
C3 C12 C21 105.11(15)
C3 C12 H12A 110.7
C21 C12 H12A 110.7
C3 C12 H12B 110.7
C21 C12 H12B 110.7
H12A C12 H12B 108.8
C17 C13 C18 117.60(19)
C17 C13 C10 123.39(17)
C18 C13 C10 118.99(17)
C6 C14 C19 120.11(18)
C6 C14 H14 119.9
C19 C14 H14 119.9
C7 C15 C4 119.70(16)
C7 C15 H15 120.2
C4 C15 H15 120.2
C9 C16 C2 121.30(16)
C9 C16 H16 119.3
C2 C16 H16 119.3
C23 C17 C13 121.1(2)
C23 C17 H17 119.5
C13 C17 H17 119.5
C25 C18 C13 122.6(2)
C25 C18 H18 118.7
C13 C18 H18 118.7
C20 C19 C14 120.14(18)
C20 C19 H19 119.9
C14 C19 H19 119.9
C19 C20 C22 119.90(17)
C19 C20 H20 120.0
C22 C20 H20 120.0
C10 C21 C12 107.57(14)
C10 C21 H21A 110.2
C12 C21 H21A 110.2
C10 C21 H21B 110.2
C12 C21 H21B 110.2
H21A C21 H21B 108.5
C11 C22 C20 120.01(18)
C11 C22 H22 120.0
C20 C22 H22 120.0
C17 C23 C24 121.0(2)
C17 C23 H23 119.5
C24 C23 H23 119.5
C18 C25 C24 118.9(2)
C18 C25 H25 120.6
C24 C25 H25 120.6
C23 C24 C25 118.8(2)
C23 C24 H24 120.6
C25 C24 H24 120.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C5 1.265(2)
O1 C5 1.2532(19)
N1 C8 1.487(2)
N1 H1A 0.8900
N1 H1B 0.8900
N1 H1C 0.8900
C1 C2 1.511(2)
C1 C3 1.529(2)
C1 C10 1.570(2)
C1 H1 0.9800
C2 C16 1.390(2)
C2 C4 1.399(2)
C3 C5 1.518(2)
C3 C12 1.538(2)
C3 H3 0.9800
C4 C15 1.401(3)
C4 H4 0.9300
C6 C14 1.386(2)
C6 C11 1.388(2)
C6 C8 1.510(2)
C7 C9 1.372(3)
C7 C15 1.384(2)
C7 H7 0.9300
C8 H8A 0.9700
C8 H8B 0.9700
C9 C16 1.386(3)
C9 H9 0.9300
C10 C13 1.520(3)
C10 C21 1.533(3)
C10 H10 0.9800
C11 C22 1.383(3)
C11 H11 0.9300
C12 C21 1.549(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C17 1.384(3)
C13 C18 1.388(3)
C14 C19 1.388(3)
C14 H14 0.9300
C15 H15 0.9300
C16 H16 0.9300
C17 C23 1.378(3)
C17 H17 0.9300
C18 C25 1.379(3)
C18 H18 0.9300
C19 C20 1.382(3)
C19 H19 0.9300
C20 C22 1.384(3)
C20 H20 0.9300
C21 H21A 0.9700
C21 H21B 0.9700
C22 H22 0.9300
C23 C24 1.387(4)
C23 H23 0.9300
C25 C24 1.404(4)
C25 H25 0.9300
C24 H24 0.9300
|
1501969.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501969.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501969
loop_
_publ_author_name
'Cohen, Daniel T.'
'Cardinal-David, Benoit'
'Roberts, John M.'
'Sarjeant, Amy A.'
'Scheidt, Karl A.'
_publ_section_title
;
NHC-catalyzed/titanium(IV)-mediated highly diastereo- and
enantioselective dimerization of enals.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1068
_journal_page_last 1071
_journal_paper_doi 10.1021/ol103112v
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C35 H38 Cl N O2'
_chemical_formula_weight 540.11
_space_group_IT_number 61
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_audit_update_record
;
2010-03-01 # Formatted by publCIF
;
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 10.9327(5)
_cell_length_b 19.6472(9)
_cell_length_c 27.9312(12)
_cell_measurement_reflns_used 3149
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 57.37
_cell_measurement_theta_min 3.16
_cell_volume 5999.5(5)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0627
_diffrn_reflns_av_sigmaI/netI 0.1170
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_number 13093
_diffrn_reflns_theta_full 59.11
_diffrn_reflns_theta_max 59.11
_diffrn_reflns_theta_min 3.16
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 1.359
_exptl_absorpt_correction_T_max 0.9681
_exptl_absorpt_correction_T_min 0.5603
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'Face-indexed, XPREP'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.196
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 2304
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.212
_refine_diff_density_min -0.228
_refine_diff_density_rms 0.057
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.954
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 358
_refine_ls_number_reflns 4187
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.954
_refine_ls_R_factor_all 0.1328
_refine_ls_R_factor_gt 0.0524
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0901
_refine_ls_wR_factor_ref 0.1139
_reflns_number_gt 2228
_reflns_number_total 4187
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103112v_si_004.cif
_cod_data_source_block n0394_0m
_cod_database_code 1501969
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.56221(8) 0.11091(5) 0.46971(3) 0.0287(3) Uani 1 1 d .
O2 O 0.6632(2) 1.03141(13) 0.36638(8) 0.0293(7) Uani 1 1 d .
N1 N 0.7030(3) 0.90106(16) 0.50346(10) 0.0191(8) Uani 1 1 d .
O1 O 0.8325(2) 0.99706(13) 0.40627(8) 0.0289(7) Uani 1 1 d .
C1 C 1.1216(3) 0.86870(19) 0.52201(13) 0.0262(10) Uani 1 1 d .
H1 H 1.1848 0.8916 0.5389 0.031 Uiso 1 1 calc R
C2 C 0.6982(3) 0.88541(19) 0.44999(12) 0.0196(9) Uani 1 1 d .
H2 H 0.7839 0.8786 0.4384 0.024 Uiso 1 1 calc R
C3 C 0.7490(3) 0.97158(18) 0.51420(11) 0.0204(10) Uani 1 1 d .
H3A H 0.6923 1.0051 0.4998 0.024 Uiso 1 1 calc R
H3B H 0.8299 0.9776 0.4988 0.024 Uiso 1 1 calc R
C4 C 0.7613(3) 0.98667(18) 0.56716(12) 0.0201(10) Uani 1 1 d .
C5 C 0.4519(3) 0.78479(19) 0.38184(12) 0.0219(9) Uani 1 1 d .
C6 C 0.8658(3) 1.01847(18) 0.58337(13) 0.0264(10) Uani 1 1 d .
H6 H 0.9289 1.0298 0.5614 0.032 Uiso 1 1 calc R
C7 C 0.7251(4) 0.9919(2) 0.39789(12) 0.0235(10) Uani 1 1 d .
C8 C 0.5710(3) 0.89972(18) 0.37856(12) 0.0219(9) Uani 1 1 d .
H8 H 0.5020 0.9279 0.3659 0.026 Uiso 1 1 calc R
C9 C 1.0013(3) 0.87455(18) 0.53700(12) 0.0237(10) Uani 1 1 d .
H9 H 0.9822 0.9023 0.5638 0.028 Uiso 1 1 calc R
C10 C 0.9379(3) 0.79865(18) 0.47437(12) 0.0250(9) Uani 1 1 d .
H10 H 0.8759 0.7731 0.4587 0.030 Uiso 1 1 calc R
C11 C 0.5183(3) 0.84068(18) 0.40860(12) 0.0190(9) Uani 1 1 d .
H11 H 0.4565 0.8616 0.4305 0.023 Uiso 1 1 calc R
C12 C 1.0577(3) 0.79445(18) 0.45851(12) 0.0232(10) Uani 1 1 d .
H12 H 1.0772 0.7676 0.4313 0.028 Uiso 1 1 calc R
C13 C 0.7768(3) 0.84648(18) 0.52938(11) 0.0230(10) Uani 1 1 d .
H13A H 0.7763 0.8567 0.5641 0.028 Uiso 1 1 calc R
H13B H 0.7357 0.8021 0.5249 0.028 Uiso 1 1 calc R
C14 C 0.8796(3) 1.0342(2) 0.63174(13) 0.0327(11) Uani 1 1 d .
H14 H 0.9520 1.0561 0.6425 0.039 Uiso 1 1 calc R
C15 C 0.9077(3) 0.84005(19) 0.51305(12) 0.0189(9) Uani 1 1 d .
C16 C 0.7886(3) 1.01806(19) 0.66413(13) 0.0282(10) Uani 1 1 d .
H16 H 0.7982 1.0284 0.6971 0.034 Uiso 1 1 calc R
C17 C 0.4450(4) 0.6786(2) 0.33818(13) 0.0397(12) Uani 1 1 d .
H17 H 0.4867 0.6401 0.3256 0.048 Uiso 1 1 calc R
C18 C 0.6497(3) 0.87614(19) 0.33696(12) 0.0221(10) Uani 1 1 d .
C19 C 0.3261(3) 0.7902(2) 0.37518(12) 0.0270(10) Uani 1 1 d .
H19 H 0.2843 0.8290 0.3871 0.032 Uiso 1 1 calc R
C20 C 0.6686(3) 0.97188(18) 0.59950(12) 0.0243(10) Uani 1 1 d .
H20 H 0.5949 0.9516 0.5886 0.029 Uiso 1 1 calc R
C21 C 0.7703(3) 0.85565(19) 0.34129(12) 0.0280(10) Uani 1 1 d .
H21 H 0.8091 0.8579 0.3717 0.034 Uiso 1 1 calc R
C22 C 0.6377(3) 0.93985(18) 0.41838(12) 0.0208(10) Uani 1 1 d .
H22 H 0.5750 0.9643 0.4380 0.025 Uiso 1 1 calc R
C23 C 0.2605(4) 0.7399(2) 0.35146(12) 0.0343(12) Uani 1 1 d .
H23 H 0.1743 0.7438 0.3482 0.041 Uiso 1 1 calc R
C24 C 1.1497(3) 0.82974(19) 0.48268(13) 0.0251(10) Uani 1 1 d .
H24 H 1.2319 0.8268 0.4719 0.030 Uiso 1 1 calc R
C25 C 0.3205(4) 0.6843(2) 0.33268(13) 0.0358(12) Uani 1 1 d .
H25 H 0.2761 0.6502 0.3160 0.043 Uiso 1 1 calc R
C26 C 0.6262(3) 0.81916(17) 0.44050(12) 0.0208(9) Uani 1 1 d .
H26A H 0.6782 0.7853 0.4239 0.025 Uiso 1 1 calc R
H26B H 0.5965 0.7992 0.4709 0.025 Uiso 1 1 calc R
C27 C 0.5108(4) 0.7294(2) 0.36225(14) 0.0351(12) Uani 1 1 d .
H27 H 0.5971 0.7255 0.3651 0.042 Uiso 1 1 calc R
C28 C 0.7310(4) 1.0852(2) 0.34214(14) 0.0399(12) Uani 1 1 d .
H28 H 0.7989 1.1014 0.3633 0.048 Uiso 1 1 calc R
C29 C 0.5966(3) 0.8726(2) 0.29193(13) 0.0323(11) Uani 1 1 d .
H29 H 0.5141 0.8867 0.2878 0.039 Uiso 1 1 calc R
C30 C 0.7816(4) 0.8279(2) 0.25779(13) 0.0392(12) Uani 1 1 d .
H30 H 0.8256 0.8110 0.2310 0.047 Uiso 1 1 calc R
C31 C 0.6619(4) 0.8490(2) 0.25301(14) 0.0389(12) Uani 1 1 d .
H31 H 0.6238 0.8473 0.2225 0.047 Uiso 1 1 calc R
C32 C 0.6834(3) 0.9867(2) 0.64795(12) 0.0292(11) Uani 1 1 d .
H32 H 0.6206 0.9751 0.6700 0.035 Uiso 1 1 calc R
C33 C 0.8360(4) 0.8318(2) 0.30204(14) 0.0341(11) Uani 1 1 d .
H33 H 0.9188 0.8182 0.3059 0.041 Uiso 1 1 calc R
C34 C 0.6403(4) 1.1424(2) 0.33430(16) 0.0695(16) Uani 1 1 d .
H34A H 0.5745 1.1267 0.3133 0.104 Uiso 1 1 calc R
H34B H 0.6821 1.1812 0.3194 0.104 Uiso 1 1 calc R
H34C H 0.6059 1.1564 0.3651 0.104 Uiso 1 1 calc R
C35 C 0.7840(4) 1.0563(2) 0.29640(14) 0.0623(16) Uani 1 1 d .
H35A H 0.8424 1.0201 0.3042 0.093 Uiso 1 1 calc R
H35B H 0.8259 1.0925 0.2787 0.093 Uiso 1 1 calc R
H35C H 0.7179 1.0375 0.2767 0.093 Uiso 1 1 calc R
H36 H 0.611(3) 0.8980(17) 0.5161(10) 0.039(11) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0210(5) 0.0309(6) 0.0343(6) -0.0043(6) 0.0017(5) 0.0012(5)
O2 0.0374(16) 0.0239(17) 0.0268(15) 0.0072(14) -0.0024(13) -0.0067(15)
N1 0.0171(18) 0.022(2) 0.0188(17) -0.0007(16) -0.0019(15) -0.0011(17)
O1 0.0227(15) 0.0360(18) 0.0282(15) -0.0009(15) -0.0014(13) -0.0063(15)
C1 0.025(2) 0.021(2) 0.033(3) 0.002(2) -0.003(2) 0.003(2)
C2 0.019(2) 0.020(2) 0.019(2) -0.004(2) 0.0017(17) -0.002(2)
C3 0.020(2) 0.023(3) 0.019(2) -0.001(2) -0.0008(17) -0.001(2)
C4 0.018(2) 0.018(2) 0.024(2) -0.001(2) -0.0027(19) 0.003(2)
C5 0.029(3) 0.017(2) 0.020(2) 0.002(2) 0.001(2) 0.002(2)
C6 0.025(2) 0.025(3) 0.029(2) 0.006(2) 0.0012(19) 0.000(2)
C7 0.033(3) 0.020(3) 0.018(2) -0.004(2) 0.002(2) 0.003(2)
C8 0.024(2) 0.019(2) 0.023(2) 0.000(2) -0.0075(19) -0.001(2)
C9 0.029(2) 0.022(3) 0.021(2) 0.001(2) -0.0022(19) 0.005(2)
C10 0.026(2) 0.024(2) 0.025(2) 0.001(2) -0.004(2) 0.004(2)
C11 0.017(2) 0.017(2) 0.022(2) -0.003(2) 0.0005(17) 0.0011(18)
C12 0.026(2) 0.024(2) 0.019(2) -0.001(2) -0.0018(19) 0.006(2)
C13 0.033(2) 0.019(2) 0.018(2) 0.004(2) -0.0032(19) 0.009(2)
C14 0.033(3) 0.033(3) 0.032(3) -0.003(2) -0.013(2) 0.001(2)
C15 0.017(2) 0.019(2) 0.021(2) 0.005(2) -0.0033(18) 0.0056(19)
C16 0.038(3) 0.027(3) 0.020(2) 0.000(2) -0.002(2) 0.003(2)
C17 0.055(3) 0.030(3) 0.034(3) -0.002(2) -0.011(2) 0.001(3)
C18 0.029(2) 0.020(3) 0.017(2) 0.003(2) -0.0006(19) -0.004(2)
C19 0.023(2) 0.040(3) 0.018(2) 0.001(2) 0.0024(19) -0.006(2)
C20 0.017(2) 0.024(3) 0.032(2) 0.007(2) -0.003(2) 0.006(2)
C21 0.032(3) 0.033(3) 0.019(2) -0.002(2) -0.002(2) -0.001(2)
C22 0.021(2) 0.021(2) 0.021(2) 0.003(2) 0.0034(18) 0.004(2)
C23 0.030(3) 0.053(3) 0.020(2) 0.007(2) -0.001(2) -0.017(3)
C24 0.021(2) 0.024(3) 0.030(2) 0.006(2) 0.001(2) 0.004(2)
C25 0.049(3) 0.035(3) 0.023(2) 0.001(2) -0.012(2) -0.015(3)
C26 0.029(2) 0.018(2) 0.015(2) 0.0032(19) -0.0004(18) 0.000(2)
C27 0.031(3) 0.034(3) 0.040(3) -0.005(3) -0.008(2) -0.002(2)
C28 0.051(3) 0.035(3) 0.034(3) 0.011(2) -0.003(2) -0.017(3)
C29 0.032(3) 0.034(3) 0.031(3) 0.006(2) 0.000(2) -0.007(2)
C30 0.045(3) 0.048(3) 0.024(3) -0.011(2) 0.011(2) -0.018(3)
C31 0.047(3) 0.047(3) 0.023(3) -0.001(2) -0.003(2) -0.018(3)
C32 0.029(3) 0.033(3) 0.026(2) 0.001(2) 0.006(2) 0.009(2)
C33 0.030(2) 0.037(3) 0.034(3) -0.005(2) 0.002(2) -0.003(2)
C34 0.099(4) 0.029(3) 0.080(4) 0.034(3) -0.011(3) -0.009(3)
C35 0.084(4) 0.072(4) 0.031(3) 0.007(3) 0.008(3) -0.029(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O2 C28 117.6(3)
C3 N1 C2 112.4(3)
C3 N1 C13 111.5(3)
C2 N1 C13 109.2(3)
C24 C1 C9 120.1(4)
N1 C2 C22 115.7(3)
N1 C2 C26 110.4(3)
C22 C2 C26 105.4(3)
N1 C3 C4 113.7(3)
C6 C4 C20 118.9(4)
C6 C4 C3 119.1(3)
C20 C4 C3 122.0(3)
C27 C5 C19 117.9(4)
C27 C5 C11 123.1(4)
C19 C5 C11 119.0(4)
C4 C6 C14 120.6(4)
O1 C7 O2 124.4(4)
O1 C7 C22 127.0(4)
O2 C7 C22 108.6(3)
C18 C8 C11 113.5(3)
C18 C8 C22 115.8(3)
C11 C8 C22 99.6(3)
C1 C9 C15 120.7(4)
C12 C10 C15 120.6(4)
C5 C11 C26 117.1(3)
C5 C11 C8 116.9(3)
C26 C11 C8 103.6(3)
C10 C12 C24 119.9(4)
C15 C13 N1 115.5(3)
C16 C14 C6 120.3(4)
C10 C15 C9 118.6(3)
C10 C15 C13 120.6(3)
C9 C15 C13 120.8(4)
C14 C16 C32 119.3(4)
C25 C17 C27 119.8(4)
C21 C18 C29 117.3(4)
C21 C18 C8 124.4(3)
C29 C18 C8 118.2(4)
C23 C19 C5 121.5(4)
C4 C20 C32 120.3(4)
C18 C21 C33 121.6(4)
C7 C22 C2 114.7(3)
C7 C22 C8 111.9(3)
C2 C22 C8 105.3(3)
C25 C23 C19 119.9(4)
C1 C24 C12 120.1(4)
C17 C25 C23 119.8(4)
C11 C26 C2 105.2(3)
C5 C27 C17 121.1(4)
O2 C28 C34 106.0(4)
O2 C28 C35 108.1(4)
C34 C28 C35 114.1(4)
C31 C29 C18 121.2(4)
C33 C30 C31 118.8(4)
C30 C31 C29 121.0(4)
C16 C32 C20 120.5(4)
C30 C33 C21 120.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.356(4)
O2 C28 1.458(4)
N1 C3 1.505(4)
N1 C2 1.527(4)
N1 C13 1.527(4)
O1 C7 1.201(4)
C1 C24 1.377(5)
C1 C9 1.381(5)
C2 C22 1.540(5)
C2 C26 1.547(5)
C3 C4 1.514(5)
C4 C6 1.382(5)
C4 C20 1.386(5)
C5 C27 1.376(5)
C5 C19 1.393(5)
C5 C11 1.510(5)
C6 C14 1.395(5)
C7 C22 1.509(5)
C8 C18 1.514(5)
C8 C11 1.547(5)
C8 C22 1.551(5)
C9 C15 1.401(5)
C10 C12 1.383(5)
C10 C15 1.394(5)
C11 C26 1.538(4)
C12 C24 1.395(5)
C13 C15 1.509(4)
C14 C16 1.379(5)
C16 C32 1.380(5)
C17 C25 1.377(5)
C17 C27 1.405(5)
C18 C21 1.384(5)
C18 C29 1.387(5)
C19 C23 1.384(5)
C20 C32 1.394(5)
C21 C33 1.393(5)
C23 C25 1.381(6)
C28 C34 1.512(6)
C28 C35 1.514(5)
C29 C31 1.381(5)
C30 C33 1.374(5)
C30 C31 1.379(5)
|
1501970.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501970.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501970
loop_
_publ_author_name
'Hager, Anastasia'
'Mazunin, Dmitry'
'Mayer, Peter'
'Trauner, Dirk'
_publ_section_title
;
Synthetic studies toward A-74528.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1386
_journal_page_last 1389
_journal_paper_doi 10.1021/ol103117j
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C29 H28 O8'
_chemical_formula_sum 'C29 H28 O8'
_chemical_formula_weight 504.528
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_block_code C29H28O8_oo110_trauner
_audit_creation_date
;
'Mon May 10 14:31:59 2010'
;
_audit_creation_method 'form98_non/compatible with shelxl97-2'
_audit_update_record 10-May-10
_cell_angle_alpha 90.00
_cell_angle_beta 113.387(5)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 18.0088(8)
_cell_length_b 8.1117(3)
_cell_length_c 18.6667(9)
_cell_measurement_reflns_used 3751
_cell_measurement_temperature 200(2)
_cell_measurement_theta_max 26.2500
_cell_measurement_theta_min 4.2026
_cell_volume 2502.8(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature 200(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
1 omega 34.00 64.00 1.0000 32.0000
omega____ theta____ kappa____ phi______ frames
- 21.2306 179.0000 -180.0000 30
2 omega -39.00 85.00 1.0000 32.0000
omega____ theta____ kappa____ phi______ frames
- 21.2306 0.0000 90.0000 124
3 omega -4.00 77.00 1.0000 32.0000
omega____ theta____ kappa____ phi______ frames
- 21.2306 38.0000 -30.0000 81
;
_diffrn_measurement_device 'CCD camera on \k-goniostat'
_diffrn_measurement_device_type 'Oxford XCalibur'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0042706129
_diffrn_orient_matrix_UB_12 -0.0244007311
_diffrn_orient_matrix_UB_13 0.0346045006
_diffrn_orient_matrix_UB_21 -0.0375184830
_diffrn_orient_matrix_UB_22 0.0420897621
_diffrn_orient_matrix_UB_23 -0.0125798061
_diffrn_orient_matrix_UB_31 -0.0203142685
_diffrn_orient_matrix_UB_32 -0.0726731882
_diffrn_orient_matrix_UB_33 -0.0188608424
_diffrn_radiation_collimation '0.5 mm collimator'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0228
_diffrn_reflns_av_sigmaI/netI 0.0544
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 9844
_diffrn_reflns_theta_full 26.36
_diffrn_reflns_theta_max 26.36
_diffrn_reflns_theta_min 4.23
_diffrn_source_current 45_mA
_diffrn_source_power 2.48_kW
_diffrn_source_type 'Spellman generator'
_diffrn_source_voltage 55_kV
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.96203
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.33896(10)
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1064
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.13
_refine_diff_density_max 0.691
_refine_diff_density_min -0.318
_refine_diff_density_rms 0.048
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.908
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 340
_refine_ls_number_reflns 5051
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.908
_refine_ls_R_factor_all 0.0808
_refine_ls_R_factor_gt 0.0490
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1247
_refine_ls_wR_factor_ref 0.1338
_reflns_number_gt 3021
_reflns_number_total 5051
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103117j_si_002.cif
_cod_data_source_block oo110
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1501970
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.17906(10) 0.34542(19) 0.31912(10) 0.0460(4) Uani 1 1 d .
H1 H 0.1845 0.2446 0.3302 0.069 Uiso 1 1 calc R
O2 O 0.21957(10) 0.5216(2) 0.25190(11) 0.0533(5) Uani 1 1 d .
O3 O 0.38807(8) 0.38957(18) 0.34391(9) 0.0419(4) Uani 1 1 d .
O4 O 0.41393(8) -0.13855(18) 0.24674(9) 0.0394(4) Uani 1 1 d .
O5 O 0.15174(8) 0.25247(19) 0.08170(8) 0.0362(4) Uani 1 1 d .
H5 H 0.1228 0.2936 0.0382 0.054 Uiso 1 1 calc R
O6 O 0.01947(8) 0.32728(17) -0.03511(8) 0.0337(4) Uani 1 1 d .
O7 O -0.23391(8) 0.15295(18) -0.04079(8) 0.0373(4) Uani 1 1 d .
O8 O 0.18824(8) 0.01473(19) 0.35322(8) 0.0398(4) Uani 1 1 d .
C1 C 0.22256(12) 0.3843(3) 0.27691(13) 0.0363(5) Uani 1 1 d .
C2 C 0.27111(11) 0.2459(2) 0.26544(11) 0.0272(4) Uani 1 1 d .
C3 C 0.35646(12) 0.2524(3) 0.30058(11) 0.0297(5) Uani 1 1 d .
C4 C 0.40186(11) 0.1219(3) 0.29270(11) 0.0308(5) Uani 1 1 d .
H4 H 0.4593 0.1267 0.3162 0.037 Uiso 1 1 calc R
C5 C 0.36363(11) -0.0156(3) 0.25063(11) 0.0288(5) Uani 1 1 d .
C6 C 0.27965(11) -0.0250(3) 0.21534(11) 0.0280(5) Uani 1 1 d .
H6 H 0.2540 -0.1205 0.1867 0.034 Uiso 1 1 calc R
C7 C 0.23354(11) 0.1067(2) 0.22245(10) 0.0254(4) Uani 1 1 d .
C8 C 0.14287(10) 0.0975(2) 0.18311(10) 0.0237(4) Uani 1 1 d .
C9 C 0.10376(11) 0.1732(2) 0.11175(11) 0.0251(4) Uani 1 1 d .
C10 C 0.01803(11) 0.1689(2) 0.07132(11) 0.0242(4) Uani 1 1 d .
C11 C -0.02635(11) 0.2458(2) -0.00240(11) 0.0252(4) Uani 1 1 d .
C12 C -0.10875(12) 0.2398(2) -0.03686(11) 0.0302(5) Uani 1 1 d .
H12 H -0.1370 0.2947 -0.0850 0.036 Uiso 1 1 calc R
C13 C -0.15184(11) 0.1513(2) -0.00048(11) 0.0285(5) Uani 1 1 d .
C14 C -0.11294(11) 0.0742(2) 0.06940(11) 0.0286(5) Uani 1 1 d .
H14 H -0.1429 0.0153 0.0930 0.034 Uiso 1 1 calc R
C15 C -0.02725(11) 0.0827(2) 0.10679(11) 0.0243(4) Uani 1 1 d .
C16 C 0.01409(11) 0.0055(2) 0.17992(11) 0.0273(4) Uani 1 1 d .
H16 H -0.0163 -0.0508 0.2039 0.033 Uiso 1 1 calc R
C17 C 0.09647(11) 0.0098(2) 0.21703(11) 0.0258(4) Uani 1 1 d .
C18 C 0.13788(12) -0.0873(3) 0.29099(11) 0.0332(5) Uani 1 1 d .
H18A H 0.0965 -0.1403 0.3059 0.040 Uiso 1 1 calc R
H18B H 0.1710 -0.1754 0.2817 0.040 Uiso 1 1 calc R
C19 C 0.25851(15) -0.0814(3) 0.40375(14) 0.0511(7) Uani 1 1 d .
H19A H 0.2927 -0.1100 0.3752 0.061 Uiso 1 1 calc R
H19B H 0.2403 -0.1851 0.4197 0.061 Uiso 1 1 calc R
C20 C 0.30639(13) 0.0199(3) 0.47477(12) 0.0396(6) Uani 1 1 d .
C21 C 0.28091(15) 0.0560(3) 0.53229(15) 0.0486(6) Uani 1 1 d .
H21 H 0.2280 0.0231 0.5259 0.058 Uiso 1 1 calc R
C22 C 0.32639(16) 0.1348(3) 0.59689(15) 0.0515(6) Uani 1 1 d .
H22 H 0.3049 0.1619 0.6344 0.062 Uiso 1 1 calc R
C23 C 0.40246(14) 0.1767(3) 0.60971(14) 0.0473(6) Uani 1 1 d .
H23 H 0.4345 0.2301 0.6573 0.057 Uiso 1 1 calc R
C24 C 0.43553(15) 0.1456(3) 0.55743(15) 0.0516(7) Uani 1 1 d .
H24 H 0.4899 0.1757 0.5680 0.062 Uiso 1 1 calc R
C25 C 0.38665(18) 0.0665(3) 0.48614(15) 0.0574(7) Uani 1 1 d .
H25 H 0.4070 0.0454 0.4472 0.069 Uiso 1 1 calc R
C26 C 0.47431(13) 0.4018(3) 0.38097(15) 0.0554(7) Uani 1 1 d .
H26A H 0.4957 0.3089 0.4169 0.083 Uiso 1 1 calc R
H26B H 0.4892 0.5055 0.4102 0.083 Uiso 1 1 calc R
H26C H 0.4971 0.3995 0.3413 0.083 Uiso 1 1 calc R
C27 C 0.37828(13) -0.2927(3) 0.21398(14) 0.0431(6) Uani 1 1 d .
H27A H 0.3440 -0.3316 0.2402 0.065 Uiso 1 1 calc R
H27B H 0.4210 -0.3737 0.2211 0.065 Uiso 1 1 calc R
H27C H 0.3454 -0.2787 0.1581 0.065 Uiso 1 1 calc R
C28 C -0.02070(14) 0.4008(3) -0.11107(12) 0.0395(5) Uani 1 1 d .
H28A H -0.0511 0.3159 -0.1486 0.059 Uiso 1 1 calc R
H28B H 0.0196 0.4499 -0.1276 0.059 Uiso 1 1 calc R
H28C H -0.0579 0.4866 -0.1086 0.059 Uiso 1 1 calc R
C29 C -0.27941(13) 0.0372(3) -0.01769(15) 0.0499(6) Uani 1 1 d .
H29A H -0.2557 -0.0728 -0.0142 0.075 Uiso 1 1 calc R
H29B H -0.3354 0.0360 -0.0563 0.075 Uiso 1 1 calc R
H29C H -0.2784 0.0687 0.0334 0.075 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0461(9) 0.0443(9) 0.0573(11) -0.0132(9) 0.0309(8) -0.0004(8)
O2 0.0484(10) 0.0323(9) 0.0785(13) 0.0003(9) 0.0244(9) 0.0024(8)
O3 0.0294(8) 0.0416(9) 0.0478(9) -0.0133(8) 0.0082(7) -0.0096(7)
O4 0.0239(8) 0.0446(9) 0.0461(9) -0.0063(7) 0.0102(7) 0.0073(7)
O5 0.0267(7) 0.0501(9) 0.0324(8) 0.0099(7) 0.0124(6) -0.0046(7)
O6 0.0325(8) 0.0385(8) 0.0285(7) 0.0071(7) 0.0103(6) -0.0033(7)
O7 0.0226(7) 0.0440(9) 0.0370(8) 0.0010(7) 0.0029(6) -0.0020(7)
O8 0.0374(8) 0.0480(9) 0.0270(8) 0.0028(7) 0.0054(6) -0.0077(8)
C1 0.0289(12) 0.0342(13) 0.0425(13) -0.0108(11) 0.0107(10) -0.0046(10)
C2 0.0252(10) 0.0294(11) 0.0275(10) 0.0021(9) 0.0112(8) 0.0008(9)
C3 0.0285(11) 0.0350(12) 0.0248(10) -0.0018(9) 0.0097(9) -0.0087(10)
C4 0.0197(10) 0.0450(13) 0.0279(11) 0.0014(10) 0.0096(8) -0.0023(10)
C5 0.0260(10) 0.0373(12) 0.0256(10) 0.0026(9) 0.0128(8) 0.0060(10)
C6 0.0232(10) 0.0323(11) 0.0270(10) -0.0010(9) 0.0084(8) -0.0003(9)
C7 0.0231(10) 0.0314(11) 0.0230(10) 0.0014(9) 0.0104(8) -0.0016(9)
C8 0.0212(10) 0.0244(10) 0.0260(10) -0.0029(8) 0.0099(8) 0.0011(9)
C9 0.0250(10) 0.0247(10) 0.0285(10) -0.0032(8) 0.0135(8) -0.0021(9)
C10 0.0248(10) 0.0222(10) 0.0254(10) -0.0031(8) 0.0096(8) 0.0002(9)
C11 0.0289(10) 0.0216(10) 0.0253(10) -0.0015(8) 0.0109(8) -0.0008(9)
C12 0.0297(11) 0.0296(11) 0.0252(10) -0.0001(9) 0.0046(9) 0.0032(10)
C13 0.0214(10) 0.0286(11) 0.0295(11) -0.0046(9) 0.0037(8) 0.0003(9)
C14 0.0241(10) 0.0283(11) 0.0327(11) -0.0021(9) 0.0106(9) -0.0032(9)
C15 0.0233(10) 0.0221(10) 0.0262(10) -0.0028(8) 0.0085(8) -0.0005(9)
C16 0.0267(10) 0.0268(11) 0.0304(11) 0.0009(9) 0.0135(9) -0.0029(9)
C17 0.0268(10) 0.0243(10) 0.0259(10) -0.0017(8) 0.0103(8) -0.0008(9)
C18 0.0284(11) 0.0370(12) 0.0300(11) 0.0044(10) 0.0072(9) -0.0016(10)
C19 0.0502(15) 0.0552(16) 0.0384(13) 0.0031(12) 0.0076(11) 0.0084(13)
C20 0.0395(13) 0.0407(13) 0.0276(11) 0.0046(10) 0.0017(10) -0.0029(11)
C21 0.0459(14) 0.0508(15) 0.0557(16) 0.0042(13) 0.0272(13) 0.0130(13)
C22 0.0528(16) 0.0563(16) 0.0468(15) 0.0010(13) 0.0211(13) 0.0083(14)
C23 0.0396(14) 0.0570(16) 0.0346(13) -0.0023(12) 0.0034(11) 0.0132(12)
C24 0.0379(13) 0.0561(16) 0.0608(16) -0.0068(14) 0.0197(12) -0.0076(12)
C25 0.083(2) 0.0544(16) 0.0513(16) 0.0052(13) 0.0439(15) 0.0110(15)
C26 0.0315(13) 0.0597(17) 0.0632(17) -0.0171(14) 0.0063(12) -0.0154(12)
C27 0.0357(13) 0.0369(13) 0.0559(15) -0.0003(11) 0.0173(11) 0.0110(11)
C28 0.0506(14) 0.0358(12) 0.0287(11) 0.0083(10) 0.0122(10) -0.0006(11)
C29 0.0253(11) 0.0537(15) 0.0602(16) 0.0021(13) 0.0058(11) -0.0078(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 109.5
C3 O3 C26 117.52(17)
C5 O4 C27 117.82(15)
C9 O5 H5 109.5
C11 O6 C28 118.73(15)
C13 O7 C29 117.01(16)
C18 O8 C19 108.90(16)
O2 C1 O1 119.8(2)
O2 C1 C2 125.5(2)
O1 C1 C2 114.69(19)
C7 C2 C3 119.16(18)
C7 C2 C1 120.95(17)
C3 C2 C1 119.85(18)
O3 C3 C4 124.38(17)
O3 C3 C2 115.35(18)
C4 C3 C2 120.20(18)
C5 C4 C3 119.84(17)
C5 C4 H4 120.1
C3 C4 H4 120.1
O4 C5 C4 115.35(17)
O4 C5 C6 123.54(18)
C4 C5 C6 121.11(18)
C7 C6 C5 119.35(18)
C7 C6 H6 120.3
C5 C6 H6 120.3
C6 C7 C2 120.33(17)
C6 C7 C8 119.28(17)
C2 C7 C8 120.38(17)
C9 C8 C17 119.15(16)
C9 C8 C7 119.29(17)
C17 C8 C7 121.54(16)
O5 C9 C8 116.30(16)
O5 C9 C10 121.59(17)
C8 C9 C10 122.11(17)
C15 C10 C9 117.81(17)
C15 C10 C11 117.22(16)
C9 C10 C11 124.96(17)
C12 C11 O6 122.68(18)
C12 C11 C10 121.72(18)
O6 C11 C10 115.59(16)
C11 C12 C13 119.58(18)
C11 C12 H12 120.2
C13 C12 H12 120.2
C14 C13 O7 124.36(19)
C14 C13 C12 121.41(17)
O7 C13 C12 114.23(17)
C13 C14 C15 119.57(19)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 120.36(17)
C16 C15 C10 119.17(17)
C14 C15 C10 120.47(17)
C17 C16 C15 121.84(18)
C17 C16 H16 119.1
C15 C16 H16 119.1
C16 C17 C8 119.88(17)
C16 C17 C18 119.67(17)
C8 C17 C18 120.33(16)
O8 C18 C17 111.62(16)
O8 C18 H18A 109.3
C17 C18 H18A 109.3
O8 C18 H18B 109.3
C17 C18 H18B 109.3
H18A C18 H18B 108.0
O8 C19 C20 108.79(19)
O8 C19 H19A 109.9
C20 C19 H19A 109.9
O8 C19 H19B 109.9
C20 C19 H19B 109.9
H19A C19 H19B 108.3
C21 C20 C25 117.8(2)
C21 C20 C19 124.0(2)
C25 C20 C19 117.9(2)
C22 C21 C20 123.0(2)
C22 C21 H21 118.5
C20 C21 H21 118.5
C21 C22 C23 120.3(3)
C21 C22 H22 119.8
C23 C22 H22 119.8
C22 C23 C24 122.4(2)
C22 C23 H23 118.8
C24 C23 H23 118.8
C23 C24 C25 118.2(2)
C23 C24 H24 120.9
C25 C24 H24 120.9
C24 C25 C20 118.2(2)
C24 C25 H25 120.9
C20 C25 H25 120.9
O3 C26 H26A 109.5
O3 C26 H26B 109.5
H26A C26 H26B 109.5
O3 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
O4 C27 H27A 109.5
O4 C27 H27B 109.5
H27A C27 H27B 109.5
O4 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
O6 C28 H28A 109.5
O6 C28 H28B 109.5
H28A C28 H28B 109.5
O6 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
O7 C29 H29A 109.5
O7 C29 H29B 109.5
H29A C29 H29B 109.5
O7 C29 H29C 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.350(3)
O1 H1 0.8400
O2 C1 1.201(3)
O3 C3 1.360(2)
O3 C26 1.431(2)
O4 C5 1.369(2)
O4 C27 1.428(3)
O5 C9 1.364(2)
O5 H5 0.8400
O6 C11 1.375(2)
O6 C28 1.440(2)
O7 C13 1.367(2)
O7 C29 1.421(3)
O8 C18 1.421(2)
O8 C19 1.467(3)
C1 C2 1.489(3)
C2 C7 1.395(3)
C2 C3 1.412(3)
C3 C4 1.381(3)
C4 C5 1.380(3)
C4 H4 0.9500
C5 C6 1.392(3)
C6 C7 1.391(3)
C6 H6 0.9500
C7 C8 1.503(2)
C8 C9 1.379(3)
C8 C17 1.423(3)
C9 C10 1.425(3)
C10 C15 1.422(3)
C10 C11 1.431(3)
C11 C12 1.364(3)
C12 C13 1.413(3)
C12 H12 0.9500
C13 C14 1.363(3)
C14 C15 1.421(3)
C14 H14 0.9500
C15 C16 1.415(3)
C16 C17 1.366(2)
C16 H16 0.9500
C17 C18 1.505(3)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.506(3)
C19 H19A 0.9900
C19 H19B 0.9900
C20 C21 1.356(3)
C20 C25 1.426(3)
C21 C22 1.323(3)
C21 H21 0.9500
C22 C23 1.338(3)
C22 H22 0.9500
C23 C24 1.354(3)
C23 H23 0.9500
C24 C25 1.424(4)
C24 H24 0.9500
C25 H25 0.9500
C26 H26A 0.9800
C26 H26B 0.9800
C26 H26C 0.9800
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C28 H28A 0.9800
C28 H28B 0.9800
C28 H28C 0.9800
C29 H29A 0.9800
C29 H29B 0.9800
C29 H29C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O8 0.84 1.91 2.747(2) 175.7
O5 H5 O6 0.84 1.84 2.5833(19) 146.5
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 C1 C2 C7 -114.7(2)
O1 C1 C2 C7 65.0(3)
O2 C1 C2 C3 67.4(3)
O1 C1 C2 C3 -112.9(2)
C26 O3 C3 C4 2.8(3)
C26 O3 C3 C2 179.79(19)
C7 C2 C3 O3 -177.52(17)
C1 C2 C3 O3 0.4(3)
C7 C2 C3 C4 -0.4(3)
C1 C2 C3 C4 177.51(19)
O3 C3 C4 C5 176.59(18)
C2 C3 C4 C5 -0.3(3)
C27 O4 C5 C4 171.04(18)
C27 O4 C5 C6 -8.9(3)
C3 C4 C5 O4 -179.55(17)
C3 C4 C5 C6 0.4(3)
O4 C5 C6 C7 -179.89(18)
C4 C5 C6 C7 0.2(3)
C5 C6 C7 C2 -0.9(3)
C5 C6 C7 C8 178.92(17)
C3 C2 C7 C6 1.0(3)
C1 C2 C7 C6 -176.91(19)
C3 C2 C7 C8 -178.83(17)
C1 C2 C7 C8 3.3(3)
C6 C7 C8 C9 -98.0(2)
C2 C7 C8 C9 81.8(2)
C6 C7 C8 C17 80.7(2)
C2 C7 C8 C17 -99.5(2)
C17 C8 C9 O5 -178.76(17)
C7 C8 C9 O5 0.0(3)
C17 C8 C9 C10 1.1(3)
C7 C8 C9 C10 179.89(17)
O5 C9 C10 C15 179.69(17)
C8 C9 C10 C15 -0.2(3)
O5 C9 C10 C11 -0.7(3)
C8 C9 C10 C11 179.43(18)
C28 O6 C11 C12 -3.9(3)
C28 O6 C11 C10 176.99(17)
C15 C10 C11 C12 1.2(3)
C9 C10 C11 C12 -178.44(19)
C15 C10 C11 O6 -179.68(16)
C9 C10 C11 O6 0.7(3)
O6 C11 C12 C13 178.93(17)
C10 C11 C12 C13 -2.0(3)
C29 O7 C13 C14 -15.0(3)
C29 O7 C13 C12 165.87(19)
C11 C12 C13 C14 1.4(3)
C11 C12 C13 O7 -179.47(17)
O7 C13 C14 C15 -179.01(18)
C12 C13 C14 C15 0.0(3)
C13 C14 C15 C16 179.05(18)
C13 C14 C15 C10 -0.8(3)
C9 C10 C15 C16 0.0(3)
C11 C10 C15 C16 -179.65(17)
C9 C10 C15 C14 179.91(17)
C11 C10 C15 C14 0.2(3)
C14 C15 C16 C17 179.28(18)
C10 C15 C16 C17 -0.8(3)
C15 C16 C17 C8 1.8(3)
C15 C16 C17 C18 -174.36(18)
C9 C8 C17 C16 -1.9(3)
C7 C8 C17 C16 179.36(17)
C9 C8 C17 C18 174.20(18)
C7 C8 C17 C18 -4.5(3)
C19 O8 C18 C17 -146.76(18)
C16 C17 C18 O8 -124.6(2)
C8 C17 C18 O8 59.2(2)
C18 O8 C19 C20 -173.14(18)
O8 C19 C20 C21 70.5(3)
O8 C19 C20 C25 -116.1(2)
C25 C20 C21 C22 1.5(4)
C19 C20 C21 C22 174.9(2)
C20 C21 C22 C23 -3.0(4)
C21 C22 C23 C24 2.0(4)
C22 C23 C24 C25 0.5(4)
C23 C24 C25 C20 -1.9(4)
C21 C20 C25 C24 0.9(4)
C19 C20 C25 C24 -172.8(2)
|
1501971.cif | #------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/19/1501971.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501971
loop_
_publ_author_name
'Hager, Anastasia'
'Mazunin, Dmitry'
'Mayer, Peter'
'Trauner, Dirk'
_publ_section_title
;
Synthetic studies toward A-74528.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1386
_journal_page_last 1389
_journal_paper_doi 10.1021/ol103117j
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C17 H23 B O6'
_chemical_formula_sum 'C17 H23 B O6'
_chemical_formula_weight 334.172
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_Int_Tables_number 19
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_block_code C17H23BO6_no207_trauner
_audit_creation_date
;
'Tue Oct 27 06:47:57 2009'
;
_audit_creation_method 'form98_non/compatible with shelxl97-2'
_audit_update_record 27-Oct-09
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 10.3923(8)
_cell_length_b 10.6376(8)
_cell_length_c 15.6535(14)
_cell_measurement_reflns_used 1773
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 26.2493
_cell_measurement_theta_min 4.2982
_cell_volume 1730.5(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
1 omega -103.00 -69.00 1.0000 85.0000
omega____ theta____ kappa____ phi______ frames
- -20.7619 179.0000 -90.0000 34
2 omega 56.00 101.00 1.0000 85.0000
omega____ theta____ kappa____ phi______ frames
- 20.9181 179.0000 150.0000 45
3 omega 59.00 99.00 1.0000 85.0000
omega____ theta____ kappa____ phi______ frames
- 20.9181 179.0000 0.0000 40
4 omega -32.00 90.00 1.0000 85.0000
omega____ theta____ kappa____ phi______ frames
- 20.9181 0.0000 150.0000 122
;
_diffrn_measurement_device 'CCD camera on \k-goniostat'
_diffrn_measurement_device_type 'Oxford XCalibur'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0631040293
_diffrn_orient_matrix_UB_12 -0.0145771748
_diffrn_orient_matrix_UB_13 0.0140878738
_diffrn_orient_matrix_UB_21 -0.0179989783
_diffrn_orient_matrix_UB_22 -0.0146380217
_diffrn_orient_matrix_UB_23 -0.0425706590
_diffrn_orient_matrix_UB_31 0.0186516312
_diffrn_orient_matrix_UB_32 -0.0634565476
_diffrn_orient_matrix_UB_33 0.0065274036
_diffrn_radiation_collimation '0.5 mm collimator'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0553
_diffrn_reflns_av_sigmaI/netI 0.0975
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 7133
_diffrn_reflns_theta_full 26.37
_diffrn_reflns_theta_max 26.37
_diffrn_reflns_theta_min 4.30
_diffrn_source_current 40_mA
_diffrn_source_power 2.00_kW
_diffrn_source_type 'Spellman generator'
_diffrn_source_voltage 50_kV
_exptl_absorpt_coefficient_mu 0.095
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.67012
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.28267(15)
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 712
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.04
_refine_diff_density_max 0.235
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 2.8(18)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.803
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 224
_refine_ls_number_reflns 2003
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.803
_refine_ls_R_factor_all 0.0896
_refine_ls_R_factor_gt 0.0440
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0850
_refine_ls_wR_factor_ref 0.0922
_reflns_number_gt 1094
_reflns_number_total 2003
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103117j_si_002.cif
_cod_data_source_block no207
_cod_database_code 1501971
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.13511(19) 0.0379(2) 0.49850(16) 0.0321(6) Uani 1 1 d .
O2 O 0.2405(2) -0.14898(19) 0.50358(18) 0.0428(7) Uani 1 1 d .
O3 O 0.5508(3) 0.1798(2) 0.30185(16) 0.0468(8) Uani 1 1 d .
O4 O 0.6737(2) 0.1487(2) 0.59395(16) 0.0384(7) Uani 1 1 d .
O5 O 0.5305(2) 0.0657(2) 0.69575(15) 0.0398(7) Uani 1 1 d .
O6 O 0.3418(2) -0.0145(2) 0.65922(18) 0.0443(7) Uani 1 1 d .
C1 C 0.0363(3) -0.0548(3) 0.5197(3) 0.0366(10) Uani 1 1 d .
C2 C 0.1037(3) -0.1819(3) 0.5002(3) 0.0309(9) Uani 1 1 d .
C3 C 0.0057(4) -0.0333(4) 0.6139(3) 0.0593(14) Uani 1 1 d .
H3A H -0.0220 0.0538 0.6223 0.089 Uiso 1 1 calc R
H3B H 0.0828 -0.0496 0.6483 0.089 Uiso 1 1 calc R
H3C H -0.0633 -0.0904 0.6316 0.089 Uiso 1 1 calc R
C4 C -0.0828(4) -0.0287(4) 0.4677(3) 0.0630(15) Uani 1 1 d .
H4A H -0.0606 -0.0278 0.4069 0.094 Uiso 1 1 calc R
H4B H -0.1184 0.0532 0.4840 0.094 Uiso 1 1 calc R
H4C H -0.1468 -0.0945 0.4785 0.094 Uiso 1 1 calc R
C5 C 0.0768(4) -0.2827(3) 0.5649(3) 0.0462(11) Uani 1 1 d .
H5A H 0.1081 -0.2557 0.6210 0.069 Uiso 1 1 calc R
H5B H 0.1208 -0.3603 0.5481 0.069 Uiso 1 1 calc R
H5C H -0.0161 -0.2979 0.5678 0.069 Uiso 1 1 calc R
C6 C 0.0791(4) -0.2303(4) 0.4111(3) 0.0578(13) Uani 1 1 d .
H6A H 0.1331 -0.3043 0.4006 0.087 Uiso 1 1 calc R
H6B H 0.1000 -0.1646 0.3695 0.087 Uiso 1 1 calc R
H6C H -0.0117 -0.2536 0.4055 0.087 Uiso 1 1 calc R
C7 C 0.3803(3) 0.0502(3) 0.4833(2) 0.0289(9) Uani 1 1 d .
C8 C 0.4140(3) 0.0854(3) 0.4007(3) 0.0347(10) Uani 1 1 d .
H8 H 0.3567 0.0685 0.3548 0.042 Uiso 1 1 calc R
C9 C 0.5322(4) 0.1456(3) 0.3843(2) 0.0323(9) Uani 1 1 d .
C10 C 0.6186(3) 0.1660(3) 0.4495(2) 0.0315(9) Uani 1 1 d .
H10 H 0.6995 0.2040 0.4382 0.038 Uiso 1 1 calc R
C11 C 0.5865(3) 0.1310(3) 0.5306(2) 0.0303(9) Uani 1 1 d .
C12 C 0.4675(4) 0.0748(3) 0.5500(2) 0.0294(9) Uani 1 1 d .
C13 C 0.4385(4) 0.0403(3) 0.6352(3) 0.0337(10) Uani 1 1 d .
C14 C 0.6202(4) 0.1658(3) 0.6781(2) 0.0379(10) Uani 1 1 d .
C15 C 0.7293(4) 0.1511(4) 0.7389(3) 0.0557(12) Uani 1 1 d .
H15A H 0.7972 0.2115 0.7247 0.084 Uiso 1 1 calc R
H15B H 0.7635 0.0655 0.7349 0.084 Uiso 1 1 calc R
H15C H 0.6990 0.1667 0.7973 0.084 Uiso 1 1 calc R
C16 C 0.5520(4) 0.2903(3) 0.6833(2) 0.0464(11) Uani 1 1 d .
H16A H 0.4859 0.2946 0.6388 0.070 Uiso 1 1 calc R
H16B H 0.6142 0.3584 0.6751 0.070 Uiso 1 1 calc R
H16C H 0.5114 0.2988 0.7396 0.070 Uiso 1 1 calc R
C17 C 0.6686(4) 0.2428(4) 0.2807(3) 0.0568(13) Uani 1 1 d .
H17A H 0.7403 0.1831 0.2841 0.085 Uiso 1 1 calc R
H17B H 0.6832 0.3118 0.3210 0.085 Uiso 1 1 calc R
H17C H 0.6629 0.2764 0.2225 0.085 Uiso 1 1 calc R
B1 B 0.2496(4) -0.0218(3) 0.4989(3) 0.0274(9) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0154(12) 0.0293(12) 0.0516(17) 0.0052(12) 0.0028(14) -0.0009(10)
O2 0.0159(12) 0.0290(13) 0.083(2) -0.0022(14) -0.0038(16) -0.0039(12)
O3 0.0352(17) 0.0699(19) 0.0352(18) 0.0073(14) 0.0016(15) -0.0161(16)
O4 0.0251(14) 0.0530(16) 0.0372(17) -0.0065(13) -0.0011(14) -0.0052(13)
O5 0.0287(14) 0.0501(16) 0.0406(18) 0.0083(12) -0.0048(14) -0.0069(13)
O6 0.0266(15) 0.0490(16) 0.057(2) 0.0128(14) -0.0038(15) -0.0095(13)
C1 0.0205(19) 0.033(2) 0.056(3) 0.0036(18) -0.002(2) -0.0019(17)
C2 0.0109(17) 0.036(2) 0.046(3) 0.000(2) -0.002(2) -0.0069(15)
C3 0.058(3) 0.052(3) 0.067(3) -0.008(2) 0.021(3) -0.006(2)
C4 0.020(2) 0.060(3) 0.110(4) 0.021(3) -0.012(3) -0.002(2)
C5 0.030(2) 0.042(2) 0.067(3) 0.012(2) -0.008(2) -0.0010(19)
C6 0.053(3) 0.070(3) 0.050(3) -0.015(2) 0.006(3) -0.018(3)
C7 0.0209(18) 0.0211(18) 0.045(3) -0.0021(17) 0.000(2) 0.0021(15)
C8 0.022(2) 0.032(2) 0.051(3) 0.0043(18) -0.009(2) -0.0078(18)
C9 0.026(2) 0.034(2) 0.036(3) 0.0007(17) 0.001(2) 0.0000(19)
C10 0.0204(19) 0.034(2) 0.041(3) -0.0048(18) -0.008(2) 0.0023(18)
C11 0.022(2) 0.031(2) 0.038(3) -0.0026(17) -0.003(2) 0.0007(16)
C12 0.027(2) 0.0224(18) 0.039(2) 0.0006(16) 0.000(2) 0.0029(17)
C13 0.026(2) 0.0288(19) 0.046(3) -0.0027(18) -0.002(2) -0.0019(19)
C14 0.033(2) 0.044(2) 0.037(3) 0.001(2) -0.003(2) -0.008(2)
C15 0.038(3) 0.086(3) 0.043(3) 0.002(2) -0.011(2) -0.016(3)
C16 0.043(2) 0.050(2) 0.046(3) -0.0085(19) 0.006(2) -0.010(2)
C17 0.044(3) 0.076(3) 0.050(3) 0.008(2) 0.004(2) -0.027(3)
B1 0.022(2) 0.029(2) 0.031(3) 0.000(2) 0.000(2) -0.003(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
B1 O1 C1 107.5(2)
B1 O2 C2 107.7(3)
C9 O3 C17 117.9(3)
C11 O4 C14 115.3(3)
C13 O5 C14 117.6(3)
O1 C1 C4 109.3(3)
O1 C1 C3 105.4(3)
C4 C1 C3 108.8(3)
O1 C1 C2 103.1(3)
C4 C1 C2 115.1(3)
C3 C1 C2 114.5(3)
O2 C2 C5 109.1(3)
O2 C2 C6 106.2(3)
C5 C2 C6 110.4(3)
O2 C2 C1 102.8(2)
C5 C2 C1 113.9(3)
C6 C2 C1 113.8(3)
C1 C3 H3A 109.5
C1 C3 H3B 109.5
H3A C3 H3B 109.5
C1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C1 C4 H4A 109.5
C1 C4 H4B 109.5
H4A C4 H4B 109.5
C1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C2 C5 H5A 109.5
C2 C5 H5B 109.5
H5A C5 H5B 109.5
C2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C2 C6 H6A 109.5
C2 C6 H6B 109.5
H6A C6 H6B 109.5
C2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 118.5(3)
C8 C7 B1 119.5(3)
C12 C7 B1 121.9(3)
C7 C8 C9 120.8(3)
C7 C8 H8 119.6
C9 C8 H8 119.6
O3 C9 C10 124.8(4)
O3 C9 C8 114.9(3)
C10 C9 C8 120.3(4)
C11 C10 C9 119.2(4)
C11 C10 H10 120.4
C9 C10 H10 120.4
O4 C11 C10 118.6(3)
O4 C11 C12 119.2(3)
C10 C11 C12 122.1(3)
C11 C12 C7 119.0(3)
C11 C12 C13 120.0(3)
C7 C12 C13 121.0(3)
O6 C13 O5 117.0(3)
O6 C13 C12 126.1(4)
O5 C13 C12 116.8(3)
O4 C14 O5 109.3(3)
O4 C14 C15 106.1(3)
O5 C14 C15 107.0(3)
O4 C14 C16 110.1(3)
O5 C14 C16 109.6(3)
C15 C14 C16 114.6(3)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O1 B1 O2 114.1(3)
O1 B1 C7 122.0(3)
O2 B1 C7 123.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 B1 1.349(4)
O1 C1 1.462(4)
O2 B1 1.358(4)
O2 C2 1.465(4)
O3 C9 1.355(4)
O3 C17 1.435(4)
O4 C11 1.356(4)
O4 C14 1.441(4)
O5 C13 1.373(4)
O5 C14 1.442(4)
O6 C13 1.221(4)
C1 C4 1.507(5)
C1 C3 1.525(5)
C1 C2 1.553(5)
C2 C5 1.501(5)
C2 C6 1.509(5)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.390(5)
C7 C12 1.408(5)
C7 B1 1.578(5)
C8 C9 1.409(5)
C8 H8 0.9500
C9 C10 1.377(5)
C10 C11 1.364(5)
C10 H10 0.9500
C11 C12 1.407(5)
C12 C13 1.416(5)
C14 C15 1.489(5)
C14 C16 1.504(5)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
B1 O1 C1 C4 -142.6(4)
B1 O1 C1 C3 100.7(4)
B1 O1 C1 C2 -19.7(4)
B1 O2 C2 C5 -137.3(3)
B1 O2 C2 C6 103.8(3)
B1 O2 C2 C1 -16.0(4)
O1 C1 C2 O2 21.3(4)
C4 C1 C2 O2 140.2(3)
C3 C1 C2 O2 -92.6(4)
O1 C1 C2 C5 139.2(3)
C4 C1 C2 C5 -101.9(4)
C3 C1 C2 C5 25.4(4)
O1 C1 C2 C6 -93.1(3)
C4 C1 C2 C6 25.8(5)
C3 C1 C2 C6 153.0(3)
C12 C7 C8 C9 -0.8(5)
B1 C7 C8 C9 -177.6(3)
C17 O3 C9 C10 -0.5(5)
C17 O3 C9 C8 179.4(3)
C7 C8 C9 O3 -177.2(3)
C7 C8 C9 C10 2.7(5)
O3 C9 C10 C11 177.7(3)
C8 C9 C10 C11 -2.2(5)
C14 O4 C11 C10 152.7(3)
C14 O4 C11 C12 -28.7(4)
C9 C10 C11 O4 178.4(3)
C9 C10 C11 C12 -0.1(5)
O4 C11 C12 C7 -176.5(3)
C10 C11 C12 C7 2.0(5)
O4 C11 C12 C13 1.6(5)
C10 C11 C12 C13 -179.9(3)
C8 C7 C12 C11 -1.5(5)
B1 C7 C12 C11 175.3(3)
C8 C7 C12 C13 -179.6(3)
B1 C7 C12 C13 -2.8(5)
C14 O5 C13 O6 -158.2(3)
C14 O5 C13 C12 24.7(4)
C11 C12 C13 O6 -176.1(3)
C7 C12 C13 O6 2.0(6)
C11 C12 C13 O5 0.7(5)
C7 C12 C13 O5 178.7(3)
C11 O4 C14 O5 51.1(4)
C11 O4 C14 C15 166.1(3)
C11 O4 C14 C16 -69.3(4)
C13 O5 C14 O4 -49.7(4)
C13 O5 C14 C15 -164.2(3)
C13 O5 C14 C16 71.0(4)
C1 O1 B1 O2 10.6(5)
C1 O1 B1 C7 -176.9(3)
C2 O2 B1 O1 4.2(5)
C2 O2 B1 C7 -168.2(3)
C8 C7 B1 O1 -76.8(5)
C12 C7 B1 O1 106.5(4)
C8 C7 B1 O2 95.0(5)
C12 C7 B1 O2 -81.7(5)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 9748307 ChemSpider
|
1501972.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501972
loop_
_publ_author_name
'Hager, Anastasia'
'Mazunin, Dmitry'
'Mayer, Peter'
'Trauner, Dirk'
_publ_section_title
;
Synthetic studies toward A-74528.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1386
_journal_page_last 1389
_journal_paper_doi 10.1021/ol103117j
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C15 H14 Br N O3'
_chemical_formula_sum 'C15 H14 Br N O3'
_chemical_formula_weight 336.181
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_Int_Tables_number 2
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_block_code C15H14BrNO3_no181_trauner
_audit_creation_date
;
'Thu Sep 24 09:57:00 2009'
;
_audit_creation_method 'form98_non/compatible with shelxl97-2'
_audit_update_record 24-Sep-09
_cell_angle_alpha 88.983(3)
_cell_angle_beta 84.074(3)
_cell_angle_gamma 83.609(3)
_cell_formula_units_Z 2
_cell_length_a 7.8896(3)
_cell_length_b 9.0992(3)
_cell_length_c 9.4428(4)
_cell_measurement_reflns_used 3355
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 26.2445
_cell_measurement_theta_min 4.3294
_cell_volume 670.06(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
1 omega -32.00 52.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -20.8087 77.0000 60.0000 84
2 omega 20.00 52.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -20.8087 77.0000 -60.0000 32
3 omega -53.00 49.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- -20.8087 77.0000 30.0000 102
4 omega -12.00 77.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- 20.9650 77.0000 -60.0000 89
5 omega -12.00 87.00 1.0000 6.0000
omega____ theta____ kappa____ phi______ frames
- 20.9650 77.0000 -180.0000 99
;
_diffrn_measurement_device 'CCD camera on \k-goniostat'
_diffrn_measurement_device_type 'Oxford XCalibur'
_diffrn_measurement_method omega-scans
_diffrn_orient_matrix_UB_11 -0.0024035172
_diffrn_orient_matrix_UB_12 -0.0671854765
_diffrn_orient_matrix_UB_13 -0.0363112170
_diffrn_orient_matrix_UB_21 0.0881069095
_diffrn_orient_matrix_UB_22 -0.0195291463
_diffrn_orient_matrix_UB_23 0.0073881820
_diffrn_orient_matrix_UB_31 -0.0219854308
_diffrn_orient_matrix_UB_32 -0.0354080627
_diffrn_orient_matrix_UB_33 0.0657698723
_diffrn_radiation_collimation '0.5 mm collimator'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0218
_diffrn_reflns_av_sigmaI/netI 0.0398
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 4733
_diffrn_reflns_theta_full 26.33
_diffrn_reflns_theta_max 26.33
_diffrn_reflns_theta_min 4.34
_diffrn_source_current 40_mA
_diffrn_source_power 2.00_kW
_diffrn_source_type 'Spellman generator'
_diffrn_source_voltage 50_kV
_exptl_absorpt_coefficient_mu 3.074
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.78568
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.66627(10)
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 340
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.18
_refine_diff_density_max 0.413
_refine_diff_density_min -0.291
_refine_diff_density_rms 0.064
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.974
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 184
_refine_ls_number_reflns 2708
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.974
_refine_ls_R_factor_all 0.0317
_refine_ls_R_factor_gt 0.0256
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0582
_refine_ls_wR_factor_ref 0.0588
_reflns_number_gt 2275
_reflns_number_total 2708
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103117j_si_002.cif
_cod_data_source_block no181
_cod_database_code 1501972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.79465(3) 0.75932(2) 0.84735(2) 0.02871(9) Uani 1 1 d .
O1 O 0.63028(17) 0.83446(15) 0.58190(15) 0.0221(3) Uani 1 1 d .
O2 O 0.53830(18) 0.78531(15) 0.32850(15) 0.0249(3) Uani 1 1 d .
O3 O 0.66083(19) 0.31157(15) 0.12127(15) 0.0256(3) Uani 1 1 d .
N1 N 1.0383(3) 0.1488(2) 0.8282(2) 0.0419(5) Uani 1 1 d .
C1 C 0.7785(2) 0.6321(2) 0.6936(2) 0.0201(4) Uani 1 1 d .
C2 C 0.7003(2) 0.6893(2) 0.5769(2) 0.0202(4) Uani 1 1 d .
C3 C 0.6878(2) 0.5972(2) 0.4601(2) 0.0186(4) Uani 1 1 d .
C4 C 0.6080(2) 0.6422(2) 0.3332(2) 0.0189(4) Uani 1 1 d .
C5 C 0.6045(3) 0.5447(2) 0.2255(2) 0.0208(4) Uani 1 1 d .
H5 H 0.5540 0.5774 0.1418 0.025 Uiso 1 1 calc R
C6 C 0.6748(3) 0.3961(2) 0.2369(2) 0.0200(4) Uani 1 1 d .
C7 C 0.7504(2) 0.3473(2) 0.3549(2) 0.0200(4) Uani 1 1 d .
H7 H 0.7979 0.2471 0.3616 0.024 Uiso 1 1 calc R
C8 C 0.7577(2) 0.4461(2) 0.4673(2) 0.0186(4) Uani 1 1 d .
C9 C 0.8358(3) 0.3936(2) 0.5892(2) 0.0193(4) Uani 1 1 d .
H9 H 0.8825 0.2929 0.5928 0.023 Uiso 1 1 calc R
C10 C 0.8463(2) 0.4826(2) 0.7018(2) 0.0192(4) Uani 1 1 d .
C11 C 0.9273(3) 0.4270(2) 0.8342(2) 0.0237(5) Uani 1 1 d .
H11A H 1.0241 0.4844 0.8469 0.028 Uiso 1 1 calc R
H11B H 0.8417 0.4452 0.9180 0.028 Uiso 1 1 calc R
C12 C 0.9907(3) 0.2685(3) 0.8294(2) 0.0278(5) Uani 1 1 d .
C13 C 0.7407(3) 0.9362(2) 0.5148(2) 0.0294(5) Uani 1 1 d .
H13A H 0.8399 0.9391 0.5688 0.044 Uiso 1 1 calc R
H13B H 0.6775 1.0351 0.5126 0.044 Uiso 1 1 calc R
H13C H 0.7799 0.9039 0.4173 0.044 Uiso 1 1 calc R
C14 C 0.4659(3) 0.8344(2) 0.2010(2) 0.0255(5) Uani 1 1 d .
H14A H 0.5538 0.8198 0.1198 0.038 Uiso 1 1 calc R
H14B H 0.4236 0.9397 0.2091 0.038 Uiso 1 1 calc R
H14C H 0.3707 0.7776 0.1868 0.038 Uiso 1 1 calc R
C15 C 0.7163(3) 0.1567(2) 0.1343(2) 0.0283(5) Uani 1 1 d .
H15A H 0.8389 0.1431 0.1467 0.042 Uiso 1 1 calc R
H15B H 0.6964 0.1057 0.0480 0.042 Uiso 1 1 calc R
H15C H 0.6515 0.1157 0.2170 0.042 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03361(14) 0.02882(13) 0.02385(13) -0.00606(9) -0.00646(9) 0.00017(9)
O1 0.0243(8) 0.0165(7) 0.0244(8) 0.0008(6) 0.0005(6) 0.0004(6)
O2 0.0320(9) 0.0191(8) 0.0234(8) 0.0010(6) -0.0083(7) 0.0035(6)
O3 0.0383(9) 0.0197(8) 0.0194(8) -0.0017(6) -0.0076(7) -0.0017(6)
N1 0.0559(15) 0.0375(13) 0.0297(12) 0.0065(10) -0.0064(10) 0.0070(11)
C1 0.0184(11) 0.0249(11) 0.0176(11) -0.0031(9) -0.0012(8) -0.0044(9)
C2 0.0157(10) 0.0192(11) 0.0248(12) 0.0015(9) 0.0014(8) -0.0023(8)
C3 0.0148(10) 0.0186(10) 0.0224(11) 0.0015(8) -0.0003(8) -0.0039(8)
C4 0.0164(10) 0.0196(10) 0.0202(11) 0.0014(8) 0.0000(8) -0.0021(8)
C5 0.0220(11) 0.0233(11) 0.0176(11) 0.0029(9) -0.0052(9) -0.0032(9)
C6 0.0216(11) 0.0195(11) 0.0191(11) -0.0004(8) 0.0006(8) -0.0056(8)
C7 0.0205(11) 0.0155(10) 0.0236(12) 0.0020(9) -0.0002(9) -0.0027(8)
C8 0.0147(10) 0.0204(11) 0.0204(11) 0.0030(8) 0.0000(8) -0.0038(8)
C9 0.0179(10) 0.0177(10) 0.0220(11) 0.0043(9) -0.0018(8) -0.0025(8)
C10 0.0174(10) 0.0234(11) 0.0172(11) 0.0019(8) -0.0021(8) -0.0037(8)
C11 0.0256(12) 0.0263(12) 0.0201(12) 0.0017(9) -0.0055(9) -0.0036(9)
C12 0.0262(12) 0.0403(15) 0.0168(12) 0.0057(10) -0.0045(9) -0.0017(11)
C13 0.0351(13) 0.0202(11) 0.0323(13) 0.0015(10) 0.0010(10) -0.0057(10)
C14 0.0301(12) 0.0206(11) 0.0252(12) 0.0035(9) -0.0068(10) 0.0028(9)
C15 0.0425(14) 0.0172(11) 0.0260(13) -0.0005(9) -0.0075(11) -0.0031(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C13 114.23(16)
C4 O2 C14 117.05(15)
C6 O3 C15 115.87(15)
C2 C1 C10 122.11(19)
C2 C1 Br1 118.84(15)
C10 C1 Br1 119.04(14)
O1 C2 C1 117.83(18)
O1 C2 C3 122.08(17)
C1 C2 C3 120.04(18)
C2 C3 C8 118.08(17)
C2 C3 C4 125.59(18)
C8 C3 C4 116.33(18)
O2 C4 C5 123.02(17)
O2 C4 C3 116.03(17)
C5 C4 C3 120.95(18)
C4 C5 C6 120.91(18)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 O3 125.17(18)
C7 C6 C5 120.61(19)
O3 C6 C5 114.22(17)
C6 C7 C8 119.77(18)
C6 C7 H7 120.1
C8 C7 H7 120.1
C9 C8 C7 119.11(18)
C9 C8 C3 119.48(18)
C7 C8 C3 121.41(17)
C10 C9 C8 122.18(18)
C10 C9 H9 118.9
C8 C9 H9 118.9
C9 C10 C1 118.10(18)
C9 C10 C11 122.68(18)
C1 C10 C11 119.22(18)
C12 C11 C10 113.54(18)
C12 C11 H11A 108.9
C10 C11 H11A 108.9
C12 C11 H11B 108.9
C10 C11 H11B 108.9
H11A C11 H11B 107.7
N1 C12 C11 178.9(2)
O1 C13 H13A 109.5
O1 C13 H13B 109.5
H13A C13 H13B 109.5
O1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.896(2)
O1 C2 1.374(2)
O1 C13 1.436(2)
O2 C4 1.357(2)
O2 C14 1.428(2)
O3 C6 1.368(2)
O3 C15 1.435(2)
N1 C12 1.112(3)
C1 C2 1.383(3)
C1 C10 1.410(3)
C2 C3 1.414(3)
C3 C8 1.426(3)
C3 C4 1.443(3)
C4 C5 1.366(3)
C5 C6 1.409(3)
C5 H5 0.9500
C6 C7 1.361(3)
C7 C8 1.413(3)
C7 H7 0.9500
C8 C9 1.412(3)
C9 C10 1.362(3)
C9 H9 0.9500
C10 C11 1.516(3)
C11 C12 1.473(3)
C11 H11A 0.9900
C11 H11B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C13 O1 C2 C1 95.9(2)
C13 O1 C2 C3 -86.8(2)
C10 C1 C2 O1 176.69(18)
Br1 C1 C2 O1 -3.3(3)
C10 C1 C2 C3 -0.6(3)
Br1 C1 C2 C3 179.45(15)
O1 C2 C3 C8 -177.22(17)
C1 C2 C3 C8 -0.1(3)
O1 C2 C3 C4 2.1(3)
C1 C2 C3 C4 179.24(19)
C14 O2 C4 C5 -2.9(3)
C14 O2 C4 C3 177.06(17)
C2 C3 C4 O2 -0.8(3)
C8 C3 C4 O2 178.56(17)
C2 C3 C4 C5 179.3(2)
C8 C3 C4 C5 -1.4(3)
O2 C4 C5 C6 -178.35(18)
C3 C4 C5 C6 1.6(3)
C15 O3 C6 C7 6.3(3)
C15 O3 C6 C5 -174.37(19)
C4 C5 C6 C7 -1.1(3)
C4 C5 C6 O3 179.59(18)
O3 C6 C7 C8 179.57(18)
C5 C6 C7 C8 0.3(3)
C6 C7 C8 C9 179.70(19)
C6 C7 C8 C3 -0.1(3)
C2 C3 C8 C9 0.2(3)
C4 C3 C8 C9 -179.16(17)
C2 C3 C8 C7 -179.95(18)
C4 C3 C8 C7 0.7(3)
C7 C8 C9 C10 -179.55(19)
C3 C8 C9 C10 0.3(3)
C8 C9 C10 C1 -0.9(3)
C8 C9 C10 C11 179.06(19)
C2 C1 C10 C9 1.1(3)
Br1 C1 C10 C9 -178.96(15)
C2 C1 C10 C11 -178.91(19)
Br1 C1 C10 C11 1.1(3)
C9 C10 C11 C12 -0.8(3)
C1 C10 C11 C12 179.21(19)
C10 C11 C12 N1 -157(13)
|
1501973.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501973.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501973
loop_
_publ_author_name
'Wang, Xu-Fan'
'An, Jing'
'Zhang, Xiao-Xiao'
'Tan, Fen'
'Chen, Jia-Rong'
'Xiao, Wen-Jing'
_publ_section_title
;
Catalytic asymmetric aza-Michael-Michael addition cascade:
enantioselective synthesis of polysubstituted 4-aminobenzopyrans.
;
_journal_issue 4
_journal_name_full 'Organic letters'
_journal_page_first 808
_journal_page_last 811
_journal_paper_doi 10.1021/ol1031188
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C20 H21 Br N2 O6'
_chemical_formula_sum 'C20 H21 Br N2 O6'
_chemical_formula_weight 465.30
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 107.486(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 8.8643(9)
_cell_length_b 11.8667(12)
_cell_length_c 10.0142(11)
_cell_measurement_reflns_used 2751
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 26.09
_cell_measurement_theta_min 2.41
_cell_volume 1004.72(18)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0665
_diffrn_reflns_av_sigmaI/netI 0.0586
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 6801
_diffrn_reflns_theta_full 28.31
_diffrn_reflns_theta_max 28.31
_diffrn_reflns_theta_min 2.13
_exptl_absorpt_coefficient_mu 2.086
_exptl_absorpt_correction_T_max 0.8186
_exptl_absorpt_correction_T_min 0.7314
_exptl_absorpt_correction_type none
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.538
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 476
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.738
_refine_diff_density_min -0.377
_refine_diff_density_rms 0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.007(10)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.957
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 270
_refine_ls_number_reflns 4343
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 0.957
_refine_ls_R_factor_all 0.0581
_refine_ls_R_factor_gt 0.0492
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1131
_refine_ls_wR_factor_ref 0.1165
_reflns_number_gt 3518
_reflns_number_total 4343
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031188_si_001.cif
_cod_data_source_block 100921bm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_database_code 1501973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.51572(6) -0.18785(6) -0.49962(5) 0.06036(16) Uani 1 1 d .
C1 C 0.4550(4) 0.0740(3) -0.2486(3) 0.0303(7) Uani 1 1 d .
C2 C 0.3218(4) 0.1297(3) -0.3355(4) 0.0336(8) Uani 1 1 d .
C3 C 0.2513(4) 0.0926(3) -0.4709(4) 0.0397(9) Uani 1 1 d .
H3 H 0.1649 0.1314 -0.5284 0.048 Uiso 1 1 calc R
C4 C 0.3077(5) -0.0008(4) -0.5210(4) 0.0437(9) Uani 1 1 d .
H4 H 0.2592 -0.0264 -0.6115 0.052 Uiso 1 1 calc R
C5 C 0.4373(5) -0.0562(3) -0.4351(4) 0.0402(8) Uani 1 1 d .
C6 C 0.5126(4) -0.0199(3) -0.3007(4) 0.0384(8) Uani 1 1 d .
H6 H 0.6011 -0.0579 -0.2453 0.046 Uiso 1 1 calc R
C7 C 0.6592(4) 0.0749(3) -0.0131(3) 0.0324(7) Uani 1 1 d .
H7 H 0.6729 -0.0034 -0.0381 0.039 Uiso 1 1 calc R
C8 C 0.8088(4) 0.1381(3) -0.0088(4) 0.0351(8) Uani 1 1 d .
C9 C 0.9369(5) 0.1356(4) 0.1138(4) 0.0398(9) Uani 1 1 d .
C10 C 1.0797(5) 0.1853(4) 0.1171(5) 0.0488(10) Uani 1 1 d .
H10 H 1.1655 0.1818 0.1979 0.059 Uiso 1 1 calc R
C11 C 1.0933(5) 0.2398(4) 0.0001(5) 0.0573(12) Uani 1 1 d .
H11 H 1.1892 0.2727 0.0020 0.069 Uiso 1 1 calc R
C12 C 0.9671(6) 0.2462(5) -0.1196(5) 0.0584(12) Uani 1 1 d .
H12 H 0.9768 0.2851 -0.1972 0.070 Uiso 1 1 calc R
C13 C 0.8263(5) 0.1951(4) -0.1242(4) 0.0481(10) Uani 1 1 d .
H13 H 0.7416 0.1988 -0.2058 0.058 Uiso 1 1 calc R
C14 C 0.6390(4) 0.0746(3) 0.1338(3) 0.0325(8) Uani 1 1 d .
C15 C 0.7919(4) 0.0252(3) 0.2369(3) 0.0353(8) Uani 1 1 d .
H15 H 0.8070 -0.0518 0.2079 0.042 Uiso 1 1 calc R
C16 C 0.5947(5) 0.1894(4) 0.1789(4) 0.0432(9) Uani 1 1 d .
H16A H 0.6773 0.2425 0.1816 0.065 Uiso 1 1 calc R
H16B H 0.5813 0.1834 0.2703 0.065 Uiso 1 1 calc R
H16C H 0.4977 0.2145 0.1133 0.065 Uiso 1 1 calc R
C17 C 0.7887(5) 0.0232(4) 0.3868(4) 0.0442(9) Uani 1 1 d .
H17A H 0.6840 0.0009 0.3883 0.053 Uiso 1 1 calc R
H17B H 0.8083 0.0988 0.4251 0.053 Uiso 1 1 calc R
C18 C 0.9094(4) -0.0562(3) 0.4791(4) 0.0357(8) Uani 1 1 d .
C19 C 1.0697(5) -0.0931(4) 0.7087(4) 0.0482(10) Uani 1 1 d .
H19A H 1.1662 -0.1001 0.6827 0.058 Uiso 1 1 calc R
H19B H 1.0248 -0.1677 0.7085 0.058 Uiso 1 1 calc R
C20 C 1.1046(6) -0.0416(4) 0.8505(4) 0.0583(13) Uani 1 1 d .
H20A H 1.1598 0.0283 0.8525 0.087 Uiso 1 1 calc R
H20B H 1.1693 -0.0921 0.9190 0.087 Uiso 1 1 calc R
H20C H 1.0074 -0.0278 0.8713 0.087 Uiso 1 1 calc R
N1 N 0.5161(4) 0.1173(3) -0.1131(3) 0.0353(7) Uani 1 1 d D
H1A H 0.493(5) 0.1865(14) -0.104(4) 0.042 Uiso 1 1 d D
N2 N 0.5075(4) -0.0107(4) 0.1301(4) 0.0455(9) Uani 1 1 d .
O1 O 0.2707(3) 0.2187(2) -0.2752(3) 0.0433(6) Uani 1 1 d D
H1 H 0.199(4) 0.249(4) -0.336(4) 0.065 Uiso 1 1 d D
O2 O 0.5185(4) -0.1028(3) 0.0791(4) 0.0654(9) Uani 1 1 d .
O3 O 0.4038(4) 0.0153(4) 0.1781(4) 0.0744(11) Uani 1 1 d .
O4 O 0.9262(3) 0.0914(3) 0.2368(3) 0.0459(7) Uani 1 1 d .
O5 O 0.9530(3) -0.1423(3) 0.4400(3) 0.0485(7) Uani 1 1 d .
O6 O 0.9573(3) -0.0203(2) 0.6093(3) 0.0427(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0845(3) 0.0507(3) 0.0520(2) -0.0147(2) 0.0297(2) -0.0001(3)
C1 0.0315(16) 0.035(2) 0.0225(14) -0.0006(15) 0.0046(12) -0.0002(14)
C2 0.0331(18) 0.036(2) 0.0295(17) 0.0026(14) 0.0059(14) -0.0032(14)
C3 0.0365(19) 0.046(2) 0.0290(17) 0.0081(15) -0.0024(15) -0.0014(16)
C4 0.047(2) 0.056(3) 0.0240(16) -0.0029(17) 0.0035(15) -0.0120(19)
C5 0.052(2) 0.037(2) 0.0357(19) -0.0051(16) 0.0187(16) -0.0040(17)
C6 0.0395(19) 0.042(2) 0.0311(17) -0.0040(16) 0.0068(15) 0.0004(16)
C7 0.0308(17) 0.035(2) 0.0262(14) -0.0006(15) 0.0010(12) 0.0053(15)
C8 0.0323(17) 0.040(2) 0.0298(17) -0.0036(15) 0.0049(14) 0.0056(15)
C9 0.039(2) 0.044(2) 0.0326(19) -0.0045(16) 0.0058(15) 0.0057(16)
C10 0.033(2) 0.060(3) 0.053(2) -0.007(2) 0.0115(17) 0.0032(19)
C11 0.044(2) 0.061(3) 0.074(3) 0.004(2) 0.028(2) -0.003(2)
C12 0.056(3) 0.071(3) 0.051(3) 0.012(2) 0.021(2) 0.000(2)
C13 0.048(2) 0.058(3) 0.037(2) 0.0056(19) 0.0110(17) 0.005(2)
C14 0.0269(16) 0.040(2) 0.0252(14) 0.0014(15) -0.0004(12) 0.0019(15)
C15 0.0317(17) 0.042(2) 0.0266(16) 0.0018(14) 0.0008(13) -0.0002(15)
C16 0.044(2) 0.048(3) 0.034(2) -0.0025(17) 0.0065(16) 0.0094(18)
C17 0.043(2) 0.056(3) 0.0286(18) 0.0049(16) 0.0025(15) 0.0064(19)
C18 0.0333(18) 0.040(2) 0.0274(17) 0.0042(15) -0.0010(14) -0.0071(16)
C19 0.059(2) 0.044(2) 0.0322(19) 0.0080(17) -0.0019(17) 0.001(2)
C20 0.073(3) 0.051(3) 0.036(2) 0.0081(19) -0.007(2) 0.004(2)
N1 0.0385(17) 0.0309(17) 0.0270(15) -0.0024(13) -0.0047(12) 0.0071(14)
N2 0.0379(19) 0.057(2) 0.0322(16) 0.0094(16) -0.0037(14) -0.0037(17)
O1 0.0418(14) 0.0444(16) 0.0352(14) 0.0032(12) -0.0014(11) 0.0135(12)
O2 0.066(2) 0.044(2) 0.073(2) 0.0044(18) 0.0007(16) -0.0135(16)
O3 0.0473(18) 0.106(3) 0.075(2) -0.002(2) 0.0259(17) -0.0199(19)
O4 0.0316(13) 0.067(2) 0.0315(13) 0.0031(12) -0.0025(10) -0.0061(12)
O5 0.0481(15) 0.0443(17) 0.0398(14) -0.0081(13) -0.0069(12) -0.0043(13)
O6 0.0502(15) 0.0423(16) 0.0272(12) 0.0035(11) -0.0013(11) 0.0035(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 N1 125.4(3)
C6 C1 C2 118.7(3)
N1 C1 C2 115.9(3)
O1 C2 C3 124.7(3)
O1 C2 C1 114.9(3)
C3 C2 C1 120.4(3)
C4 C3 C2 120.6(3)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.0(3)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 121.9(4)
C4 C5 Br1 120.1(3)
C6 C5 Br1 118.0(3)
C5 C6 C1 119.4(4)
C5 C6 H6 120.3
C1 C6 H6 120.3
N1 C7 C8 115.2(3)
N1 C7 C14 109.5(3)
C8 C7 C14 109.1(3)
N1 C7 H7 107.6
C8 C7 H7 107.6
C14 C7 H7 107.6
C13 C8 C9 118.5(4)
C13 C8 C7 122.3(3)
C9 C8 C7 119.1(3)
O4 C9 C10 116.8(3)
O4 C9 C8 122.7(3)
C10 C9 C8 120.3(4)
C11 C10 C9 119.5(4)
C11 C10 H10 120.2
C9 C10 H10 120.2
C12 C11 C10 120.8(4)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C13 119.8(4)
C11 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C8 120.9(4)
C12 C13 H13 119.5
C8 C13 H13 119.5
C16 C14 C7 113.3(3)
C16 C14 N2 109.6(3)
C7 C14 N2 106.5(3)
C16 C14 C15 113.1(3)
C7 C14 C15 108.0(3)
N2 C14 C15 105.8(3)
O4 C15 C17 105.9(3)
O4 C15 C14 110.7(3)
C17 C15 C14 113.2(3)
O4 C15 H15 109.0
C17 C15 H15 109.0
C14 C15 H15 109.0
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 C18 113.3(3)
C15 C17 H17A 108.9
C18 C17 H17A 108.9
C15 C17 H17B 108.9
C18 C17 H17B 108.9
H17A C17 H17B 107.7
O5 C18 O6 124.1(4)
O5 C18 C17 124.6(4)
O6 C18 C17 111.2(3)
O6 C19 C20 108.1(4)
O6 C19 H19A 110.1
C20 C19 H19A 110.1
O6 C19 H19B 110.1
C20 C19 H19B 110.1
H19A C19 H19B 108.4
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C1 N1 C7 123.1(3)
C1 N1 H1A 115(3)
C7 N1 H1A 117(3)
O3 N2 O2 124.3(4)
O3 N2 C14 119.3(4)
O2 N2 C14 116.4(4)
C2 O1 H1 107(4)
C9 O4 C15 119.7(3)
C18 O6 C19 115.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.900(4)
C1 C6 1.390(5)
C1 N1 1.399(4)
C1 C2 1.404(5)
C2 O1 1.361(5)
C2 C3 1.383(5)
C3 C4 1.372(6)
C3 H3 0.9300
C4 C5 1.377(6)
C4 H4 0.9300
C5 C6 1.380(5)
C6 H6 0.9300
C7 N1 1.450(4)
C7 C8 1.514(5)
C7 C14 1.534(5)
C7 H7 0.9800
C8 C13 1.387(5)
C8 C9 1.400(5)
C9 O4 1.368(5)
C9 C10 1.388(6)
C10 C11 1.375(6)
C10 H10 0.9300
C11 C12 1.374(7)
C11 H11 0.9300
C12 C13 1.376(6)
C12 H12 0.9300
C13 H13 0.9300
C14 C16 1.523(5)
C14 N2 1.535(5)
C14 C15 1.551(4)
C15 O4 1.426(4)
C15 C17 1.510(5)
C15 H15 0.9800
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 C18 1.514(5)
C17 H17A 0.9700
C17 H17B 0.9700
C18 O5 1.200(5)
C18 O6 1.315(5)
C19 O6 1.461(5)
C19 C20 1.490(6)
C19 H19A 0.9700
C19 H19B 0.9700
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
N1 H1A 0.858(10)
N2 O3 1.199(5)
N2 O2 1.222(5)
O1 H1 0.817(10)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O5 0.817(10) 1.932(19) 2.722(4) 162(5) 2_655
N1 H1A O2 0.858(10) 2.518(14) 3.362(5) 168(4) 2_655
N1 H1A O1 0.858(10) 2.22(4) 2.587(4) 106(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 O1 178.2(3)
N1 C1 C2 O1 0.1(5)
C6 C1 C2 C3 -1.1(5)
N1 C1 C2 C3 -179.2(3)
O1 C2 C3 C4 -177.4(3)
C1 C2 C3 C4 1.8(6)
C2 C3 C4 C5 -1.0(6)
C3 C4 C5 C6 -0.5(6)
C3 C4 C5 Br1 178.6(3)
C4 C5 C6 C1 1.2(6)
Br1 C5 C6 C1 -177.9(3)
N1 C1 C6 C5 177.5(4)
C2 C1 C6 C5 -0.4(5)
N1 C7 C8 C13 -27.5(5)
C14 C7 C8 C13 -151.1(3)
N1 C7 C8 C9 155.1(3)
C14 C7 C8 C9 31.5(5)
C13 C8 C9 O4 173.3(4)
C7 C8 C9 O4 -9.2(6)
C13 C8 C9 C10 -2.6(6)
C7 C8 C9 C10 174.9(4)
O4 C9 C10 C11 -174.4(4)
C8 C9 C10 C11 1.8(6)
C9 C10 C11 C12 0.4(7)
C10 C11 C12 C13 -1.8(7)
C11 C12 C13 C8 0.9(7)
C9 C8 C13 C12 1.3(6)
C7 C8 C13 C12 -176.2(4)
N1 C7 C14 C16 -55.7(4)
C8 C7 C14 C16 71.2(4)
N1 C7 C14 N2 64.9(4)
C8 C7 C14 N2 -168.2(3)
N1 C7 C14 C15 178.2(3)
C8 C7 C14 C15 -54.9(4)
C16 C14 C15 O4 -66.6(4)
C7 C14 C15 O4 59.7(4)
N2 C14 C15 O4 173.5(3)
C16 C14 C15 C17 52.2(4)
C7 C14 C15 C17 178.4(3)
N2 C14 C15 C17 -67.8(4)
O4 C15 C17 C18 -76.8(4)
C14 C15 C17 C18 161.7(3)
C15 C17 C18 O5 -32.0(6)
C15 C17 C18 O6 149.9(3)
C6 C1 N1 C7 6.3(6)
C2 C1 N1 C7 -175.7(3)
C8 C7 N1 C1 94.3(4)
C14 C7 N1 C1 -142.2(4)
C16 C14 N2 O3 -9.9(4)
C7 C14 N2 O3 -132.9(4)
C15 C14 N2 O3 112.4(4)
C16 C14 N2 O2 171.3(3)
C7 C14 N2 O2 48.3(4)
C15 C14 N2 O2 -66.4(4)
C10 C9 O4 C15 -171.1(4)
C8 C9 O4 C15 12.9(6)
C17 C15 O4 C9 -161.5(3)
C14 C15 O4 C9 -38.5(4)
O5 C18 O6 C19 -0.5(5)
C17 C18 O6 C19 177.7(3)
C20 C19 O6 C18 -177.6(4)
|
1501974.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501974.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501974
loop_
_publ_author_name
'Deb, Indubhusan'
'Das, Deepankar'
'Seidel, Daniel'
_publ_section_title
;
Redox isomerization via azomethine ylide intermediates: N-alkyl indoles
from indolines and aldehydes.
;
_journal_issue 4
_journal_name_full 'Organic letters'
_journal_page_first 812
_journal_page_last 815
_journal_paper_doi 10.1021/ol1031359
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C21 H20 Br N O3'
_chemical_formula_weight 414.29
_chemical_name_systematic
;
?
;
_space_group_IT_number 9
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'C -2yc'
_symmetry_space_group_name_H-M 'C 1 c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 114.023(1)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 20.2038(13)
_cell_length_b 5.1569(3)
_cell_length_c 18.6200(12)
_cell_measurement_reflns_used 9383
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 32.08
_cell_measurement_theta_min 2.40
_cell_volume 1771.96(19)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type 'Bruker SMART APEX CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0436
_diffrn_reflns_av_sigmaI/netI 0.0390
_diffrn_reflns_limit_h_max 29
_diffrn_reflns_limit_h_min -29
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_number 10869
_diffrn_reflns_theta_full 32.08
_diffrn_reflns_theta_max 32.08
_diffrn_reflns_theta_min 2.21
_exptl_absorpt_coefficient_mu 2.341
_exptl_absorpt_correction_T_max 0.8723
_exptl_absorpt_correction_T_min 0.5121
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Bruker SAINT (SADABS)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.553
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description rod
_exptl_crystal_F_000 848
_exptl_crystal_size_max 0.33
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.497
_refine_diff_density_min -0.325
_refine_diff_density_rms 0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.478(4)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.005
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 237
_refine_ls_number_reflns 5899
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.005
_refine_ls_R_factor_all 0.0238
_refine_ls_R_factor_gt 0.0231
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.5500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0610
_refine_ls_wR_factor_ref 0.0614
_reflns_number_gt 5764
_reflns_number_total 5899
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031359_si_002.cif
_cod_data_source_block ibd1023
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M Cc
_cod_database_code 1501974
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.337658(7) -0.66790(3) 0.390895(7) 0.01666(4) Uani 1 1 d .
O1 O 0.16438(6) 0.3416(2) 0.73360(7) 0.0171(2) Uani 1 1 d .
O2 O 0.39223(6) 0.0907(3) 0.80969(7) 0.0205(2) Uani 1 1 d .
O3 O 0.40813(6) 0.4560(3) 0.75249(7) 0.0182(2) Uani 1 1 d .
N1 N 0.22910(6) 0.0887(3) 0.56549(7) 0.0122(2) Uani 1 1 d .
C1 C 0.18728(7) 0.0327(3) 0.61227(8) 0.0124(2) Uani 1 1 d .
H1 H 0.1665 -0.1462 0.6007 0.015 Uiso 1 1 calc R
C2 C 0.12728(8) 0.2306(3) 0.59563(9) 0.0139(2) Uani 1 1 d .
C3 C 0.07992(8) 0.2832(4) 0.51815(9) 0.0181(3) Uani 1 1 d .
H3 H 0.0842 0.1871 0.4767 0.022 Uiso 1 1 calc R
C4 C 0.02651(8) 0.4733(4) 0.50005(10) 0.0211(3) Uani 1 1 d .
H4 H -0.0052 0.5067 0.4469 0.025 Uiso 1 1 calc R
C5 C 0.02040(8) 0.6132(4) 0.56077(11) 0.0205(3) Uani 1 1 d .
H5 H -0.0155 0.7445 0.5491 0.025 Uiso 1 1 calc R
C6 C 0.06620(8) 0.5628(4) 0.63842(10) 0.0181(3) Uani 1 1 d .
H6 H 0.0614 0.6582 0.6797 0.022 Uiso 1 1 calc R
C7 C 0.11946(8) 0.3715(3) 0.65585(9) 0.0139(3) Uani 1 1 d .
C8 C 0.20626(8) 0.1063(4) 0.75357(9) 0.0158(3) Uani 1 1 d .
H8A H 0.1741 -0.0407 0.7517 0.019 Uiso 1 1 calc R
H8B H 0.2437 0.1200 0.8080 0.019 Uiso 1 1 calc R
C9 C 0.24293(8) 0.0512(3) 0.69827(8) 0.0126(2) Uani 1 1 d .
H9 H 0.2703 -0.1156 0.7138 0.015 Uiso 1 1 calc R
C10 C 0.29381(7) 0.2653(3) 0.69471(8) 0.0123(2) Uani 1 1 d .
H10 H 0.2715 0.4369 0.6966 0.015 Uiso 1 1 calc R
C11 C 0.29628(7) 0.2356(3) 0.61286(8) 0.0125(2) Uani 1 1 d .
H11 H 0.2944 0.4107 0.5890 0.015 Uiso 1 1 calc R
C12 C 0.35923(8) 0.0778(3) 0.60817(9) 0.0163(3) Uani 1 1 d .
H12A H 0.3930 0.1912 0.5963 0.020 Uiso 1 1 calc R
H12B H 0.3864 -0.0158 0.6580 0.020 Uiso 1 1 calc R
C13 C 0.32122(8) -0.1084(3) 0.54179(9) 0.0129(2) Uani 1 1 d .
C14 C 0.34915(8) -0.2740(3) 0.50286(9) 0.0143(2) Uani 1 1 d .
H14 H 0.3994 -0.2740 0.5139 0.017 Uiso 1 1 calc R
C15 C 0.30107(8) -0.4419(3) 0.44654(8) 0.0144(3) Uani 1 1 d .
C16 C 0.22766(8) -0.4481(3) 0.43075(8) 0.0160(3) Uani 1 1 d .
H16 H 0.1966 -0.5679 0.3935 0.019 Uiso 1 1 calc R
C17 C 0.19964(8) -0.2777(4) 0.46967(9) 0.0151(3) Uani 1 1 d .
H17 H 0.1495 -0.2788 0.4591 0.018 Uiso 1 1 calc R
C18 C 0.24692(8) -0.1061(3) 0.52431(8) 0.0127(2) Uani 1 1 d .
C19 C 0.36885(8) 0.2566(4) 0.75981(9) 0.0148(3) Uani 1 1 d .
C20 C 0.48287(8) 0.4686(4) 0.80969(10) 0.0234(4) Uani 1 1 d .
H20A H 0.5057 0.2952 0.8168 0.028 Uiso 1 1 calc R
H20B H 0.4851 0.5285 0.8611 0.028 Uiso 1 1 calc R
C21 C 0.52150(10) 0.6565(4) 0.77858(13) 0.0287(4) Uani 1 1 d .
H21A H 0.5163 0.6008 0.7262 0.043 Uiso 1 1 calc R
H21B H 0.5730 0.6617 0.8141 0.043 Uiso 1 1 calc R
H21C H 0.5004 0.8296 0.7751 0.043 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02132(6) 0.01645(6) 0.01478(6) -0.00190(6) 0.00996(4) 0.00127(6)
O1 0.0168(5) 0.0208(6) 0.0141(5) -0.0012(4) 0.0067(4) 0.0022(4)
O2 0.0185(5) 0.0231(6) 0.0167(5) 0.0045(5) 0.0040(4) -0.0006(5)
O3 0.0139(4) 0.0225(6) 0.0157(4) 0.0016(5) 0.0034(4) -0.0052(4)
N1 0.0123(5) 0.0136(6) 0.0118(5) -0.0020(4) 0.0060(4) -0.0023(4)
C1 0.0134(5) 0.0126(6) 0.0126(5) 0.0001(5) 0.0067(4) -0.0016(5)
C2 0.0122(5) 0.0161(7) 0.0147(6) 0.0001(5) 0.0067(5) -0.0008(5)
C3 0.0133(6) 0.0254(8) 0.0155(6) 0.0001(6) 0.0058(5) -0.0005(6)
C4 0.0124(6) 0.0297(9) 0.0200(6) 0.0048(7) 0.0054(5) 0.0020(6)
C5 0.0126(6) 0.0225(8) 0.0277(8) 0.0040(7) 0.0095(6) 0.0029(6)
C6 0.0147(6) 0.0187(8) 0.0231(7) -0.0010(6) 0.0100(5) -0.0003(5)
C7 0.0123(5) 0.0167(7) 0.0145(6) 0.0000(5) 0.0073(5) -0.0010(5)
C8 0.0161(6) 0.0189(7) 0.0138(6) 0.0010(6) 0.0076(5) 0.0010(5)
C9 0.0134(5) 0.0125(6) 0.0122(5) 0.0002(5) 0.0055(4) -0.0013(5)
C10 0.0121(5) 0.0129(6) 0.0122(5) -0.0001(5) 0.0051(4) -0.0012(5)
C11 0.0128(5) 0.0138(6) 0.0118(5) -0.0010(5) 0.0058(4) -0.0017(5)
C12 0.0125(5) 0.0199(7) 0.0174(6) -0.0054(6) 0.0069(5) -0.0016(5)
C13 0.0134(6) 0.0134(6) 0.0128(5) -0.0013(5) 0.0063(5) -0.0011(5)
C14 0.0155(6) 0.0150(6) 0.0150(6) -0.0012(5) 0.0088(5) -0.0008(5)
C15 0.0180(6) 0.0135(7) 0.0139(5) -0.0002(5) 0.0088(5) 0.0003(5)
C16 0.0165(6) 0.0182(7) 0.0126(6) -0.0021(5) 0.0053(5) -0.0013(5)
C17 0.0133(6) 0.0186(7) 0.0130(6) -0.0019(5) 0.0050(5) -0.0020(5)
C18 0.0139(6) 0.0137(6) 0.0101(5) 0.0012(5) 0.0047(5) 0.0006(5)
C19 0.0142(6) 0.0182(8) 0.0123(6) -0.0013(6) 0.0057(5) -0.0007(6)
C20 0.0136(6) 0.0336(10) 0.0186(7) 0.0026(7) 0.0019(5) -0.0046(6)
C21 0.0189(7) 0.0323(11) 0.0337(10) 0.0002(8) 0.0096(7) -0.0062(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 C8 115.81(12)
C19 O3 C20 116.22(13)
C18 N1 C1 121.57(13)
C18 N1 C11 108.33(11)
C1 N1 C11 110.75(11)
N1 C1 C2 110.58(12)
N1 C1 C9 104.58(11)
C2 C1 C9 110.80(12)
N1 C1 H1 110.3
C2 C1 H1 110.3
C9 C1 H1 110.3
C3 C2 C7 118.32(15)
C3 C2 C1 119.78(14)
C7 C2 C1 121.85(13)
C2 C3 C4 121.62(16)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 119.02(15)
C5 C4 H4 120.5
C3 C4 H4 120.5
C6 C5 C4 120.58(16)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 119.89(16)
C5 C6 H6 120.1
C7 C6 H6 120.1
O1 C7 C6 116.22(14)
O1 C7 C2 123.16(14)
C6 C7 C2 120.56(14)
O1 C8 C9 112.33(13)
O1 C8 H8A 109.1
C9 C8 H8A 109.1
O1 C8 H8B 109.1
C9 C8 H8B 109.1
H8A C8 H8B 107.9
C8 C9 C10 114.60(13)
C8 C9 C1 111.41(11)
C10 C9 C1 102.65(11)
C8 C9 H9 109.3
C10 C9 H9 109.3
C1 C9 H9 109.3
C19 C10 C9 114.67(13)
C19 C10 C11 111.26(11)
C9 C10 C11 105.21(12)
C19 C10 H10 108.5
C9 C10 H10 108.5
C11 C10 H10 108.5
N1 C11 C12 105.76(12)
N1 C11 C10 104.23(11)
C12 C11 C10 117.69(12)
N1 C11 H11 109.6
C12 C11 H11 109.6
C10 C11 H11 109.6
C13 C12 C11 103.08(11)
C13 C12 H12A 111.1
C11 C12 H12A 111.1
C13 C12 H12B 111.1
C11 C12 H12B 111.1
H12A C12 H12B 109.1
C14 C13 C18 120.77(14)
C14 C13 C12 130.14(13)
C18 C13 C12 109.01(13)
C13 C14 C15 117.92(14)
C13 C14 H14 121.0
C15 C14 H14 121.0
C16 C15 C14 121.82(14)
C16 C15 Br1 119.33(12)
C14 C15 Br1 118.86(11)
C15 C16 C17 119.92(14)
C15 C16 H16 120.0
C17 C16 H16 120.0
C18 C17 C16 118.44(14)
C18 C17 H17 120.8
C16 C17 H17 120.8
C17 C18 N1 127.19(13)
C17 C18 C13 121.07(15)
N1 C18 C13 111.71(13)
O2 C19 O3 124.00(14)
O2 C19 C10 126.13(15)
O3 C19 C10 109.80(13)
O3 C20 C21 107.13(15)
O3 C20 H20A 110.3
C21 C20 H20A 110.3
O3 C20 H20B 110.3
C21 C20 H20B 110.3
H20A C20 H20B 108.5
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.8978(15)
O1 C7 1.3687(19)
O1 C8 1.439(2)
O2 C19 1.208(2)
O3 C19 1.340(2)
O3 C20 1.4523(18)
N1 C18 1.397(2)
N1 C1 1.4682(18)
N1 C11 1.4899(19)
C1 C2 1.517(2)
C1 C9 1.5400(19)
C1 H1 1.0000
C2 C3 1.395(2)
C2 C7 1.398(2)
C3 C4 1.394(2)
C3 H3 0.9500
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.387(2)
C5 H5 0.9500
C6 C7 1.397(2)
C6 H6 0.9500
C8 C9 1.520(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.528(2)
C9 H9 1.0000
C10 C19 1.508(2)
C10 C11 1.553(2)
C10 H10 1.0000
C11 C12 1.542(2)
C11 H11 1.0000
C12 C13 1.506(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.381(2)
C13 C18 1.4006(19)
C14 C15 1.401(2)
C14 H14 0.9500
C15 C16 1.390(2)
C16 C17 1.397(2)
C16 H16 0.9500
C17 C18 1.393(2)
C17 H17 0.9500
C20 C21 1.500(3)
C20 H20A 0.9900
C20 H20B 0.9900
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C18 N1 C1 C2 -133.67(14)
C11 N1 C1 C2 97.46(14)
C18 N1 C1 C9 107.02(14)
C11 N1 C1 C9 -21.85(17)
N1 C1 C2 C3 51.29(19)
C9 C1 C2 C3 166.78(14)
N1 C1 C2 C7 -126.11(15)
C9 C1 C2 C7 -10.6(2)
C7 C2 C3 C4 0.9(2)
C1 C2 C3 C4 -176.56(15)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C7 0.6(3)
C8 O1 C7 C6 164.80(14)
C8 O1 C7 C2 -18.3(2)
C5 C6 C7 O1 177.27(16)
C5 C6 C7 C2 0.3(2)
C3 C2 C7 O1 -177.82(15)
C1 C2 C7 O1 -0.4(2)
C3 C2 C7 C6 -1.0(2)
C1 C2 C7 C6 176.41(14)
C7 O1 C8 C9 47.31(18)
O1 C8 C9 C10 58.17(16)
O1 C8 C9 C1 -57.81(17)
N1 C1 C9 C8 157.13(13)
C2 C1 C9 C8 37.97(17)
N1 C1 C9 C10 34.02(15)
C2 C1 C9 C10 -85.14(14)
C8 C9 C10 C19 82.70(16)
C1 C9 C10 C19 -156.36(13)
C8 C9 C10 C11 -154.73(12)
C1 C9 C10 C11 -33.79(14)
C18 N1 C11 C12 -10.30(15)
C1 N1 C11 C12 125.37(13)
C18 N1 C11 C10 -135.03(13)
C1 N1 C11 C10 0.64(17)
C19 C10 C11 N1 145.80(14)
C9 C10 C11 N1 21.06(15)
C19 C10 C11 C12 29.09(19)
C9 C10 C11 C12 -95.66(15)
N1 C11 C12 C13 14.09(15)
C10 C11 C12 C13 129.97(14)
C11 C12 C13 C14 169.88(17)
C11 C12 C13 C18 -13.45(17)
C18 C13 C14 C15 -1.1(2)
C12 C13 C14 C15 175.23(16)
C13 C14 C15 C16 -1.3(2)
C13 C14 C15 Br1 179.02(12)
C14 C15 C16 C17 2.1(2)
Br1 C15 C16 C17 -178.19(12)
C15 C16 C17 C18 -0.5(2)
C16 C17 C18 N1 175.73(15)
C16 C17 C18 C13 -1.8(2)
C1 N1 C18 C17 54.2(2)
C11 N1 C18 C17 -175.91(15)
C1 N1 C18 C13 -128.07(14)
C11 N1 C18 C13 1.85(17)
C14 C13 C18 C17 2.7(2)
C12 C13 C18 C17 -174.33(15)
C14 C13 C18 N1 -175.21(15)
C12 C13 C18 N1 7.75(18)
C20 O3 C19 O2 -0.8(2)
C20 O3 C19 C10 -177.90(14)
C9 C10 C19 O2 4.7(2)
C11 C10 C19 O2 -114.50(18)
C9 C10 C19 O3 -178.20(13)
C11 C10 C19 O3 62.57(18)
C19 O3 C20 C21 164.90(16)
|
1501975.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501975.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501975
loop_
_publ_author_name
'Kislukhin, Alexander A.'
'Higginson, Cody J.'
'Finn, M. G.'
_publ_section_title
;
Aqueous-phase deactivation and intramolecular [2 + 2 + 2] cycloaddition
of oxanorbornadiene esters.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1832
_journal_page_last 1835
_journal_paper_doi 10.1021/ol103153f
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C28 H26 N2 O7 S'
_chemical_formula_weight 534.57
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 103.5480(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 15.8048(3)
_cell_length_b 8.9561(2)
_cell_length_c 18.1279(3)
_cell_measurement_reflns_used 7949
_cell_measurement_temperature 153(2)
_cell_measurement_theta_max 31.27
_cell_measurement_theta_min 2.31
_cell_volume 2494.59(8)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 153(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0269
_diffrn_reflns_av_sigmaI/netI 0.0293
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_number 27330
_diffrn_reflns_theta_full 32.77
_diffrn_reflns_theta_max 32.77
_diffrn_reflns_theta_min 1.54
_exptl_absorpt_coefficient_mu 0.182
_exptl_absorpt_correction_T_max 0.9820
_exptl_absorpt_correction_T_min 0.9274
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details 'Bruker SADABS'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.423
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1120
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.613
_refine_diff_density_min -0.717
_refine_diff_density_rms 0.061
_refine_ls_extinction_coef 0
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.116
_refine_ls_hydrogen_treatment fixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 346
_refine_ls_number_reflns 8937
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.116
_refine_ls_R_factor_all 0.0596
_refine_ls_R_factor_gt 0.0447
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1418
_refine_ls_wR_factor_ref 0.1549
_reflns_number_gt 6199
_reflns_number_total 8937
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103153f_si_003.cif
_cod_data_source_block C28H26N2O7S
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/n
_cod_database_code 1501975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S -0.02644(2) 0.68117(4) 0.195493(18) 0.01861(10) Uani 1 1 d .
O1 O 0.04570(7) 0.58148(12) 0.20024(6) 0.0251(2) Uani 1 1 d .
O2 O -0.11054(7) 0.62098(12) 0.19471(6) 0.0272(2) Uani 1 1 d .
O3 O 0.31195(7) 0.91492(14) 0.10534(6) 0.0324(3) Uani 1 1 d .
O4 O 0.24602(7) 0.79360(13) 0.18535(5) 0.0269(2) Uani 1 1 d .
O5 O 0.19908(7) 1.06130(12) -0.05819(6) 0.0261(2) Uani 1 1 d .
O6 O 0.29944(6) 0.90099(13) -0.07873(6) 0.0266(2) Uani 1 1 d .
O7 O 0.04005(6) 0.80701(11) -0.02624(5) 0.0183(2) Uani 1 1 d .
N1 N -0.03617(7) 0.77499(13) 0.11754(6) 0.0183(2) Uani 1 1 d .
H1 H -0.0857 0.7773 0.0831 0.022 Uiso 1 1 calc R
N2 N -0.03683(10) 1.25066(19) 0.41706(10) 0.0414(4) Uani 1 1 d .
C1 C 0.00550(9) 0.81320(15) 0.26953(7) 0.0195(3) Uani 1 1 d .
C2 C 0.09239(9) 0.81554(18) 0.30519(8) 0.0261(3) Uani 1 1 d .
H2 H 0.1301 0.7402 0.2944 0.031 Uiso 1 1 calc R
C3 C 0.12570(10) 0.9290(2) 0.35750(9) 0.0336(4) Uani 1 1 d .
H3 H 0.1861 0.9316 0.3811 0.040 Uiso 1 1 calc R
C4 C 0.07168(10) 1.0352(2) 0.37436(9) 0.0312(3) Uani 1 1 d .
H4 H 0.0950 1.1120 0.4094 0.037 Uiso 1 1 calc R
C5 C -0.01875(9) 1.03342(17) 0.34068(8) 0.0228(3) Uani 1 1 d .
C6 C -0.07547(10) 1.14149(19) 0.36144(9) 0.0279(3) Uani 1 1 d .
C7 C -0.16279(10) 1.1366(2) 0.32884(9) 0.0309(3) Uani 1 1 d .
H7 H -0.2006 1.2068 0.3439 0.037 Uiso 1 1 calc R
C8 C -0.19730(9) 1.02979(19) 0.27361(9) 0.0287(3) Uani 1 1 d .
H8 H -0.2579 1.0300 0.2507 0.034 Uiso 1 1 calc R
C9 C -0.14451(8) 0.92483(17) 0.25224(8) 0.0227(3) Uani 1 1 d .
H9 H -0.1688 0.8533 0.2145 0.027 Uiso 1 1 calc R
C10 C -0.05388(8) 0.92207(16) 0.28590(7) 0.0186(2) Uani 1 1 d .
C11 C -0.08304(16) 1.2670(3) 0.47721(12) 0.0523(5) Uani 1 1 d .
H11A H -0.1403 1.3115 0.4564 0.078 Uiso 1 1 calc R
H11B H -0.0496 1.3319 0.5171 0.078 Uiso 1 1 calc R
H11C H -0.0904 1.1687 0.4986 0.078 Uiso 1 1 calc R
C12 C -0.02543(16) 1.3927(3) 0.38125(16) 0.0635(7) Uani 1 1 d .
H12A H 0.0049 1.3758 0.3406 0.095 Uiso 1 1 calc R
H12B H 0.0090 1.4603 0.4192 0.095 Uiso 1 1 calc R
H12C H -0.0825 1.4374 0.3599 0.095 Uiso 1 1 calc R
C13 C 0.04093(8) 0.85630(16) 0.10648(7) 0.0189(2) Uani 1 1 d .
H13A H 0.0838 0.8642 0.1558 0.023 Uiso 1 1 calc R
H13B H 0.0235 0.9588 0.0888 0.023 Uiso 1 1 calc R
C14 C 0.08317(8) 0.78233(15) 0.05034(7) 0.0173(2) Uani 1 1 d .
C15 C 0.18161(8) 0.78571(15) 0.05435(7) 0.0174(2) Uani 1 1 d .
C16 C 0.19126(8) 0.79575(15) -0.02735(7) 0.0175(2) Uani 1 1 d .
C17 C 0.09785(8) 0.73467(16) -0.06453(7) 0.0183(2) Uani 1 1 d .
C19 C 0.12007(8) 0.57804(16) -0.02569(7) 0.0198(3) Uani 1 1 d .
H19 H 0.0743 0.4997 -0.0410 0.024 Uiso 1 1 calc R
C20 C 0.13202(8) 0.63840(15) 0.05585(7) 0.0180(2) Uani 1 1 d .
H20 H 0.1417 0.5721 0.1014 0.022 Uiso 1 1 calc R
C21 C 0.25277(8) 0.84008(16) 0.11602(8) 0.0201(3) Uani 1 1 d .
C22 C 0.31610(12) 0.8468(3) 0.24651(9) 0.0434(5) Uani 1 1 d .
H22A H 0.3085 0.9548 0.2547 0.052 Uiso 1 1 calc R
H22B H 0.3726 0.8324 0.2329 0.052 Uiso 1 1 calc R
C23 C 0.31552(9) 0.7649(2) 0.31557(8) 0.0290(3) Uani 1 1 d .
C24 C 0.31954(11) 0.7071(2) 0.37483(9) 0.0351(4) Uani 1 1 d .
H24 H 0.3228 0.6606 0.4225 0.042 Uiso 1 1 calc R
C25 C 0.06473(9) 0.74500(17) -0.14910(8) 0.0237(3) Uani 1 1 d .
H25A H 0.0071 0.6986 -0.1639 0.036 Uiso 1 1 calc R
H25B H 0.1049 0.6930 -0.1741 0.036 Uiso 1 1 calc R
H25C H 0.0605 0.8502 -0.1645 0.036 Uiso 1 1 calc R
C26 C 0.20705(9) 0.54329(17) -0.04340(8) 0.0232(3) Uani 1 1 d .
H26 H 0.2284 0.4473 -0.0521 0.028 Uiso 1 1 calc R
C27 C 0.24796(9) 0.67366(16) -0.04446(7) 0.0208(3) Uani 1 1 d .
C28 C 0.32489(9) 0.74376(18) -0.06524(8) 0.0257(3) Uani 1 1 d .
H28A H 0.3776 0.7342 -0.0234 0.031 Uiso 1 1 calc R
H28B H 0.3363 0.6974 -0.1115 0.031 Uiso 1 1 calc R
C30 C 0.22694(8) 0.93492(17) -0.05465(7) 0.0210(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.01866(16) 0.01769(17) 0.01980(16) -0.00191(11) 0.00514(12) -0.00145(11)
O1 0.0259(5) 0.0205(5) 0.0286(5) -0.0014(4) 0.0053(4) 0.0048(4)
O2 0.0234(5) 0.0272(6) 0.0331(5) -0.0029(4) 0.0111(4) -0.0081(4)
O3 0.0251(5) 0.0448(7) 0.0258(5) 0.0010(5) 0.0032(4) -0.0141(5)
O4 0.0213(5) 0.0410(7) 0.0158(4) -0.0013(4) -0.0009(4) -0.0100(4)
O5 0.0224(5) 0.0243(5) 0.0304(5) 0.0048(4) 0.0036(4) -0.0005(4)
O6 0.0215(5) 0.0316(6) 0.0292(5) 0.0029(4) 0.0113(4) -0.0007(4)
O7 0.0151(4) 0.0225(5) 0.0166(4) -0.0012(3) 0.0020(3) 0.0011(3)
N1 0.0137(5) 0.0230(6) 0.0175(5) -0.0008(4) 0.0021(4) -0.0004(4)
N2 0.0324(7) 0.0396(9) 0.0503(9) -0.0250(7) 0.0058(6) 0.0039(6)
C1 0.0187(6) 0.0224(7) 0.0173(6) -0.0018(5) 0.0038(5) 0.0001(5)
C2 0.0193(6) 0.0332(8) 0.0239(6) -0.0072(6) 0.0012(5) 0.0049(5)
C3 0.0190(6) 0.0470(10) 0.0311(7) -0.0148(7) -0.0015(6) 0.0045(6)
C4 0.0222(7) 0.0392(9) 0.0295(7) -0.0147(7) 0.0003(6) 0.0007(6)
C5 0.0203(6) 0.0260(7) 0.0220(6) -0.0049(5) 0.0047(5) 0.0018(5)
C6 0.0257(7) 0.0291(8) 0.0288(7) -0.0070(6) 0.0061(6) 0.0040(6)
C7 0.0241(7) 0.0342(9) 0.0342(8) -0.0052(7) 0.0066(6) 0.0083(6)
C8 0.0186(6) 0.0380(9) 0.0293(7) -0.0008(6) 0.0052(5) 0.0061(6)
C9 0.0186(6) 0.0289(7) 0.0207(6) -0.0008(5) 0.0049(5) 0.0012(5)
C10 0.0179(6) 0.0213(6) 0.0171(5) 0.0007(5) 0.0051(4) 0.0008(5)
C11 0.0614(13) 0.0524(13) 0.0419(10) -0.0214(9) 0.0101(9) 0.0068(10)
C12 0.0562(13) 0.0440(13) 0.102(2) -0.0317(13) 0.0415(14) -0.0188(10)
C13 0.0184(6) 0.0181(6) 0.0208(6) -0.0019(5) 0.0062(5) -0.0016(5)
C14 0.0140(5) 0.0212(6) 0.0161(5) -0.0007(5) 0.0021(4) -0.0006(4)
C15 0.0149(5) 0.0210(6) 0.0156(5) -0.0015(5) 0.0023(4) -0.0006(5)
C16 0.0151(5) 0.0208(6) 0.0163(5) -0.0008(5) 0.0030(4) 0.0006(4)
C17 0.0166(5) 0.0217(6) 0.0165(5) -0.0025(5) 0.0037(4) -0.0011(5)
C19 0.0192(6) 0.0199(6) 0.0197(6) -0.0027(5) 0.0035(5) -0.0008(5)
C20 0.0173(6) 0.0186(6) 0.0177(5) -0.0002(5) 0.0036(4) -0.0007(5)
C21 0.0163(6) 0.0244(7) 0.0187(6) -0.0015(5) 0.0019(5) -0.0009(5)
C22 0.0340(9) 0.0704(14) 0.0192(7) 0.0018(7) -0.0071(6) -0.0272(9)
C23 0.0193(6) 0.0406(9) 0.0238(7) -0.0045(6) -0.0015(5) -0.0022(6)
C24 0.0318(8) 0.0429(10) 0.0273(7) 0.0020(7) 0.0002(6) 0.0031(7)
C25 0.0243(6) 0.0279(7) 0.0174(6) -0.0014(5) 0.0018(5) -0.0023(6)
C26 0.0239(6) 0.0235(7) 0.0222(6) -0.0036(5) 0.0056(5) 0.0039(5)
C27 0.0185(6) 0.0260(7) 0.0179(6) -0.0020(5) 0.0045(5) 0.0031(5)
C28 0.0208(6) 0.0308(8) 0.0274(7) -0.0004(6) 0.0092(5) 0.0031(6)
C30 0.0175(6) 0.0259(7) 0.0186(6) 0.0007(5) 0.0023(5) -0.0013(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 119.30(7)
O2 S1 N1 106.77(6)
O1 S1 N1 106.66(6)
O2 S1 C1 110.98(6)
O1 S1 C1 106.77(6)
N1 S1 C1 105.46(6)
C21 O4 C22 113.38(11)
C30 O6 C28 112.41(11)
C14 O7 C17 100.99(9)
C13 N1 S1 117.56(9)
C6 N2 C11 112.94(15)
C6 N2 C12 111.00(17)
C11 N2 C12 112.45(17)
C2 C1 C10 121.56(13)
C2 C1 S1 116.27(10)
C10 C1 S1 121.83(10)
C1 C2 C3 120.23(14)
C4 C3 C2 120.12(14)
C3 C4 C5 121.22(14)
C4 C5 C10 119.82(13)
C4 C5 C6 120.72(13)
C10 C5 C6 119.46(12)
C7 C6 C5 119.75(14)
C7 C6 N2 123.05(14)
C5 C6 N2 117.20(13)
C6 C7 C8 121.00(14)
C9 C8 C7 120.63(13)
C8 C9 C10 120.66(13)
C9 C10 C5 118.45(12)
C9 C10 C1 124.55(13)
C5 C10 C1 116.99(11)
N1 C13 C14 112.88(11)
O7 C14 C20 108.87(10)
O7 C14 C13 114.18(10)
C20 C14 C13 129.98(11)
O7 C14 C15 107.01(10)
C20 C14 C15 60.88(8)
C13 C14 C15 124.45(11)
C21 C15 C16 119.05(11)
C21 C15 C20 124.94(11)
C16 C15 C20 103.58(10)
C21 C15 C14 128.78(11)
C16 C15 C14 106.54(10)
C20 C15 C14 58.05(8)
C27 C16 C30 104.48(11)
C27 C16 C15 111.10(11)
C30 C16 C15 120.00(11)
C27 C16 C17 101.87(11)
C30 C16 C17 122.44(11)
C15 C16 C17 95.64(10)
O7 C17 C25 111.03(11)
O7 C17 C16 106.14(10)
C25 C17 C16 118.96(11)
O7 C17 C19 106.79(10)
C25 C17 C19 119.99(12)
C16 C17 C19 91.70(10)
C26 C19 C20 111.18(11)
C26 C19 C17 101.95(11)
C20 C19 C17 94.63(10)
C14 C20 C15 61.06(9)
C14 C20 C19 107.03(10)
C15 C20 C19 103.42(10)
O3 C21 O4 123.71(12)
O3 C21 C15 123.19(12)
O4 C21 C15 113.08(11)
O4 C22 C23 109.56(14)
C24 C23 C22 174.56(18)
C27 C26 C19 106.83(12)
C26 C27 C16 108.72(12)
C26 C27 C28 142.76(13)
C16 C27 C28 107.98(12)
O6 C28 C27 103.75(11)
O5 C30 O6 121.20(13)
O5 C30 C16 129.38(12)
O6 C30 C16 109.41(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4312(10)
S1 O1 1.4348(10)
S1 N1 1.6201(12)
S1 C1 1.7712(14)
O3 C21 1.2027(17)
O4 C21 1.3518(16)
O4 C22 1.4517(18)
O5 C30 1.2107(18)
O6 C30 1.3528(16)
O6 C28 1.4692(19)
O7 C14 1.4133(15)
O7 C17 1.4259(15)
N1 C13 1.4731(16)
N2 C6 1.434(2)
N2 C11 1.455(3)
N2 C12 1.458(3)
C1 C2 1.3743(19)
C1 C10 1.4317(18)
C2 C3 1.406(2)
C3 C4 1.360(2)
C4 C5 1.4167(19)
C5 C10 1.4251(19)
C5 C6 1.428(2)
C6 C7 1.369(2)
C7 C8 1.400(2)
C8 C9 1.372(2)
C9 C10 1.4196(18)
C13 C14 1.4962(18)
C14 C20 1.4938(19)
C14 C15 1.5406(17)
C15 C21 1.4706(18)
C15 C16 1.5268(17)
C15 C20 1.5380(18)
C16 C27 1.4917(18)
C16 C30 1.4991(19)
C16 C17 1.5705(18)
C17 C25 1.5024(18)
C17 C19 1.5719(19)
C19 C26 1.5153(18)
C19 C20 1.5434(18)
C22 C23 1.453(2)
C23 C24 1.181(2)
C26 C27 1.337(2)
C27 C28 1.4929(19)
|
1501976.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501976.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501976
loop_
_publ_author_name
'Chen, Xiang-Yu'
'Wen, Ming-Wei'
'Ye, Song'
'Wang, Zhi-Xiang'
_publ_section_title
;
Unusual formal [4 + 2] cycloaddition of ethyl allenoate with
arylidenoxindoles: synthesis of dihydropyran-fused indoles.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1138
_journal_page_last 1141
_journal_paper_doi 10.1021/ol103165y
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C24 H23 N O5'
_chemical_formula_sum 'C24 H23 N O5'
_chemical_formula_weight 405.43
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 100.57(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 10.145(2)
_cell_length_b 9.4248(19)
_cell_length_c 21.513(4)
_cell_measurement_reflns_used 6103
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.4745
_cell_measurement_theta_min 1.9260
_cell_volume 2022.1(7)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type 'Saturn724+ CCD'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0307
_diffrn_reflns_av_sigmaI/netI 0.0386
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 6583
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 1.93
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.4860
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.332
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 856
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.50
_exptl_crystal_size_min 0.40
_refine_diff_density_max 0.312
_refine_diff_density_min -0.318
_refine_diff_density_rms 0.124
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.211
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 271
_refine_ls_number_reflns 3479
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.211
_refine_ls_R_factor_all 0.0621
_refine_ls_R_factor_gt 0.0531
_refine_ls_shift/su_max 0.009
_refine_ls_shift/su_mean 0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.7843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1374
_refine_ls_wR_factor_ref 0.1504
_reflns_number_gt 3235
_reflns_number_total 3479
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103165y_si_002.cif
_cod_data_source_block a
_cod_original_cell_volume 2022.0(7)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1501976
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.47842(17) 0.78592(19) 0.40547(8) 0.0484(5) Uani 1 1 d .
O2 O -0.32488(16) 0.62882(16) 0.38632(7) 0.0363(4) Uani 1 1 d .
O3 O -0.20638(14) 0.46634(15) 0.47606(6) 0.0314(4) Uani 1 1 d .
O4 O 0.09426(16) 0.14305(17) 0.54181(7) 0.0387(4) Uani 1 1 d .
O5 O 0.09835(15) 0.14374(16) 0.43763(7) 0.0332(4) Uani 1 1 d .
N1 N -0.37299(17) 0.64142(18) 0.48427(8) 0.0299(4) Uani 1 1 d .
C1 C -0.5363(2) 0.7938(2) 0.53199(11) 0.0366(5) Uani 1 1 d .
H1A H -0.5677 0.8478 0.4949 0.044 Uiso 1 1 calc R
C2 C -0.5831(2) 0.8184(3) 0.58761(12) 0.0395(6) Uani 1 1 d .
H2A H -0.6479 0.8906 0.5886 0.047 Uiso 1 1 calc R
C3 C -0.5373(2) 0.7395(3) 0.64205(11) 0.0399(6) Uani 1 1 d .
H3A H -0.5706 0.7597 0.6796 0.048 Uiso 1 1 calc R
C4 C -0.4438(2) 0.6320(2) 0.64240(11) 0.0366(5) Uani 1 1 d .
H4A H -0.4142 0.5774 0.6795 0.044 Uiso 1 1 calc R
C5 C -0.3939(2) 0.6056(2) 0.58711(10) 0.0300(5) Uani 1 1 d .
C6 C -0.4416(2) 0.6871(2) 0.53259(10) 0.0300(5) Uani 1 1 d .
C7 C -0.3982(2) 0.6936(2) 0.42235(10) 0.0328(5) Uani 1 1 d .
C8 C -0.3467(3) 0.6758(3) 0.32091(11) 0.0465(6) Uani 1 1 d .
H8A H -0.3136 0.7739 0.3182 0.056 Uiso 1 1 calc R
H8B H -0.4435 0.6736 0.3024 0.056 Uiso 1 1 calc R
C9 C -0.2711(3) 0.5759(3) 0.28630(12) 0.0598(8) Uani 1 1 d .
H9A H -0.2825 0.6045 0.2418 0.090 Uiso 1 1 calc R
H9B H -0.3055 0.4794 0.2890 0.090 Uiso 1 1 calc R
H9C H -0.1757 0.5785 0.3054 0.090 Uiso 1 1 calc R
C10 C -0.2857(2) 0.5334(2) 0.51140(10) 0.0279(5) Uani 1 1 d .
C11 C -0.2950(2) 0.5081(2) 0.57166(10) 0.0295(5) Uani 1 1 d .
C12 C -0.2115(2) 0.3947(2) 0.60893(10) 0.0301(5) Uani 1 1 d .
H12A H -0.2636 0.3040 0.6043 0.036 Uiso 1 1 calc R
C13 C -0.1735(2) 0.4300(2) 0.67881(10) 0.0320(5) Uani 1 1 d .
C14 C -0.1137(2) 0.5587(3) 0.69876(11) 0.0381(5) Uani 1 1 d .
H14A H -0.0932 0.6245 0.6685 0.046 Uiso 1 1 calc R
C15 C -0.0837(2) 0.5919(3) 0.76255(12) 0.0468(6) Uani 1 1 d .
H15A H -0.0427 0.6802 0.7757 0.056 Uiso 1 1 calc R
C16 C -0.1131(2) 0.4972(3) 0.80721(12) 0.0491(7) Uani 1 1 d .
H16A H -0.0933 0.5206 0.8509 0.059 Uiso 1 1 calc R
C17 C -0.1715(2) 0.3685(3) 0.78789(11) 0.0471(6) Uani 1 1 d .
H17A H -0.1905 0.3023 0.8184 0.057 Uiso 1 1 calc R
C18 C -0.2024(2) 0.3354(3) 0.72386(11) 0.0383(5) Uani 1 1 d .
H18A H -0.2438 0.2472 0.7108 0.046 Uiso 1 1 calc R
C19 C -0.0858(2) 0.3754(2) 0.57867(10) 0.0314(5) Uani 1 1 d .
H19A H -0.0232 0.4548 0.5922 0.038 Uiso 1 1 calc R
H19B H -0.0401 0.2864 0.5949 0.038 Uiso 1 1 calc R
C20 C -0.1147(2) 0.3699(2) 0.50791(10) 0.0277(5) Uani 1 1 d .
C21 C -0.0567(2) 0.2899(2) 0.46966(10) 0.0295(5) Uani 1 1 d .
H21A H -0.0880 0.3010 0.4255 0.035 Uiso 1 1 calc R
C22 C 0.0512(2) 0.1859(2) 0.48911(10) 0.0294(5) Uani 1 1 d .
C23 C 0.2046(2) 0.0383(2) 0.44765(10) 0.0326(5) Uani 1 1 d .
H23A H 0.1706 -0.0532 0.4609 0.039 Uiso 1 1 calc R
H23B H 0.2797 0.0703 0.4808 0.039 Uiso 1 1 calc R
C24 C 0.2502(2) 0.0224(2) 0.38552(10) 0.0359(5) Uani 1 1 d .
H24A H 0.3225 -0.0479 0.3897 0.054 Uiso 1 1 calc R
H24B H 0.2832 0.1139 0.3730 0.054 Uiso 1 1 calc R
H24C H 0.1748 -0.0091 0.3533 0.054 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0487(10) 0.0510(11) 0.0452(10) 0.0120(8) 0.0081(8) 0.0230(9)
O2 0.0394(9) 0.0379(9) 0.0306(8) 0.0031(7) 0.0041(7) 0.0082(7)
O3 0.0344(8) 0.0302(8) 0.0289(8) -0.0013(6) 0.0038(6) 0.0071(6)
O4 0.0413(9) 0.0435(9) 0.0310(8) 0.0052(7) 0.0057(7) 0.0116(7)
O5 0.0343(8) 0.0331(8) 0.0326(8) 0.0004(6) 0.0074(6) 0.0092(6)
N1 0.0292(9) 0.0271(9) 0.0321(9) -0.0017(7) 0.0015(7) 0.0033(7)
C1 0.0295(11) 0.0345(12) 0.0436(13) -0.0044(10) 0.0006(10) 0.0027(9)
C2 0.0301(11) 0.0392(13) 0.0495(14) -0.0103(11) 0.0079(10) 0.0038(10)
C3 0.0350(12) 0.0430(13) 0.0434(13) -0.0083(11) 0.0119(10) 0.0003(10)
C4 0.0340(12) 0.0385(12) 0.0383(12) -0.0014(10) 0.0091(10) -0.0010(10)
C5 0.0249(10) 0.0286(11) 0.0359(11) -0.0040(9) 0.0036(9) -0.0038(8)
C6 0.0257(10) 0.0285(11) 0.0349(11) -0.0069(9) 0.0030(9) -0.0027(8)
C7 0.0308(11) 0.0302(11) 0.0364(12) -0.0001(9) 0.0031(9) 0.0004(9)
C8 0.0515(15) 0.0516(15) 0.0358(13) 0.0132(11) 0.0064(11) 0.0108(12)
C9 0.076(2) 0.0695(19) 0.0378(14) 0.0054(13) 0.0195(14) 0.0154(16)
C10 0.0265(10) 0.0244(10) 0.0314(11) -0.0017(8) 0.0018(8) 0.0012(8)
C11 0.0279(10) 0.0276(10) 0.0311(11) -0.0026(9) 0.0010(9) -0.0015(8)
C12 0.0330(11) 0.0258(10) 0.0311(11) -0.0020(8) 0.0045(9) -0.0008(9)
C13 0.0294(11) 0.0361(12) 0.0302(11) 0.0011(9) 0.0045(9) 0.0070(9)
C14 0.0317(12) 0.0418(13) 0.0411(12) -0.0042(10) 0.0075(10) -0.0018(10)
C15 0.0354(13) 0.0550(16) 0.0479(15) -0.0154(12) 0.0023(11) -0.0023(11)
C16 0.0356(13) 0.0778(19) 0.0319(12) -0.0097(12) 0.0014(10) 0.0079(13)
C17 0.0404(13) 0.0675(17) 0.0339(13) 0.0108(12) 0.0082(11) 0.0063(12)
C18 0.0350(12) 0.0407(13) 0.0395(13) 0.0020(10) 0.0076(10) 0.0037(10)
C19 0.0344(11) 0.0306(11) 0.0288(11) -0.0004(9) 0.0049(9) 0.0054(9)
C20 0.0276(10) 0.0252(10) 0.0295(11) 0.0028(8) 0.0028(8) 0.0007(8)
C21 0.0305(11) 0.0282(11) 0.0285(11) -0.0002(8) 0.0023(9) 0.0004(9)
C22 0.0290(11) 0.0269(10) 0.0324(12) -0.0009(9) 0.0059(9) -0.0020(9)
C23 0.0296(11) 0.0280(11) 0.0402(12) 0.0011(9) 0.0060(9) 0.0038(9)
C24 0.0318(11) 0.0348(12) 0.0404(13) -0.0043(10) 0.0048(10) 0.0039(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O2 C8 115.23(17)
C10 O3 C20 116.12(16)
C22 O5 C23 116.53(16)
C7 N1 C10 129.93(18)
C7 N1 C6 124.21(18)
C10 N1 C6 105.78(17)
C2 C1 C6 117.3(2)
C2 C1 H1A 121.3
C6 C1 H1A 121.3
C1 C2 C3 121.5(2)
C1 C2 H2A 119.2
C3 C2 H2A 119.2
C4 C3 C2 121.1(2)
C4 C3 H3A 119.4
C2 C3 H3A 119.4
C3 C4 C5 118.7(2)
C3 C4 H4A 120.7
C5 C4 H4A 120.7
C4 C5 C6 119.18(19)
C4 C5 C11 133.2(2)
C6 C5 C11 107.57(18)
C1 C6 C5 122.2(2)
C1 C6 N1 130.1(2)
C5 C6 N1 107.71(18)
O1 C7 O2 125.6(2)
O1 C7 N1 122.5(2)
O2 C7 N1 111.90(18)
O2 C8 C9 106.8(2)
O2 C8 H8A 110.4
C9 C8 H8A 110.4
O2 C8 H8B 110.4
C9 C8 H8B 110.4
H8A C8 H8B 108.6
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 O3 127.78(19)
C11 C10 N1 112.38(18)
O3 C10 N1 119.83(18)
C10 C11 C5 106.57(18)
C10 C11 C12 120.74(19)
C5 C11 C12 132.69(19)
C11 C12 C13 112.85(17)
C11 C12 C19 106.70(17)
C13 C12 C19 111.32(17)
C11 C12 H12A 108.6
C13 C12 H12A 108.6
C19 C12 H12A 108.6
C18 C13 C14 118.8(2)
C18 C13 C12 120.2(2)
C14 C13 C12 121.0(2)
C15 C14 C13 120.5(2)
C15 C14 H14A 119.7
C13 C14 H14A 119.7
C16 C15 C14 120.4(2)
C16 C15 H15A 119.8
C14 C15 H15A 119.8
C17 C16 C15 119.6(2)
C17 C16 H16A 120.2
C15 C16 H16A 120.2
C16 C17 C18 120.1(2)
C16 C17 H17A 120.0
C18 C17 H17A 120.0
C13 C18 C17 120.7(2)
C13 C18 H18A 119.7
C17 C18 H18A 119.7
C20 C19 C12 114.18(17)
C20 C19 H19A 108.7
C12 C19 H19A 108.7
C20 C19 H19B 108.7
C12 C19 H19B 108.7
H19A C19 H19B 107.6
C21 C20 O3 113.45(18)
C21 C20 C19 128.49(19)
O3 C20 C19 117.88(17)
C20 C21 C22 126.28(19)
C20 C21 H21A 116.9
C22 C21 H21A 116.9
O4 C22 O5 123.51(19)
O4 C22 C21 127.74(19)
O5 C22 C21 108.75(17)
O5 C23 C24 106.14(17)
O5 C23 H23A 110.5
C24 C23 H23A 110.5
O5 C23 H23B 110.5
C24 C23 H23B 110.5
H23A C23 H23B 108.7
C23 C24 H24A 109.5
C23 C24 H24B 109.5
H24A C24 H24B 109.5
C23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.201(3)
O2 C7 1.318(3)
O2 C8 1.453(3)
O3 C10 1.360(2)
O3 C20 1.388(2)
O4 C22 1.207(2)
O5 C22 1.345(2)
O5 C23 1.453(2)
N1 C7 1.399(3)
N1 C10 1.404(3)
N1 C6 1.420(3)
C1 C2 1.385(3)
C1 C6 1.390(3)
C1 H1A 0.9500
C2 C3 1.393(3)
C2 H2A 0.9500
C3 C4 1.387(3)
C3 H3A 0.9500
C4 C5 1.398(3)
C4 H4A 0.9500
C5 C6 1.411(3)
C5 C11 1.443(3)
C8 C9 1.496(4)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.338(3)
C11 C12 1.501(3)
C12 C13 1.519(3)
C12 C19 1.545(3)
C12 H12A 1.0000
C13 C18 1.387(3)
C13 C14 1.388(3)
C14 C15 1.386(3)
C14 H14A 0.9500
C15 C16 1.383(4)
C15 H15A 0.9500
C16 C17 1.380(4)
C16 H16A 0.9500
C17 C18 1.391(3)
C17 H17A 0.9500
C18 H18A 0.9500
C19 C20 1.497(3)
C19 H19A 0.9900
C19 H19B 0.9900
C20 C21 1.329(3)
C21 C22 1.472(3)
C21 H21A 0.9500
C23 C24 1.500(3)
C23 H23A 0.9900
C23 H23B 0.9900
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.0(3)
C1 C2 C3 C4 -0.7(4)
C2 C3 C4 C5 1.2(3)
C3 C4 C5 C6 -1.0(3)
C3 C4 C5 C11 177.5(2)
C2 C1 C6 C5 0.1(3)
C2 C1 C6 N1 -177.7(2)
C4 C5 C6 C1 0.4(3)
C11 C5 C6 C1 -178.50(19)
C4 C5 C6 N1 178.62(18)
C11 C5 C6 N1 -0.3(2)
C7 N1 C6 C1 -5.0(3)
C10 N1 C6 C1 178.0(2)
C7 N1 C6 C5 176.96(18)
C10 N1 C6 C5 0.0(2)
C8 O2 C7 O1 -0.4(3)
C8 O2 C7 N1 179.14(19)
C10 N1 C7 O1 178.6(2)
C6 N1 C7 O1 2.4(3)
C10 N1 C7 O2 -0.9(3)
C6 N1 C7 O2 -177.15(18)
C7 O2 C8 C9 -171.6(2)
C20 O3 C10 C11 -6.9(3)
C20 O3 C10 N1 174.47(17)
C7 N1 C10 C11 -176.4(2)
C6 N1 C10 C11 0.4(2)
C7 N1 C10 O3 2.4(3)
C6 N1 C10 O3 179.16(17)
O3 C10 C11 C5 -179.20(19)
N1 C10 C11 C5 -0.5(2)
O3 C10 C11 C12 0.3(3)
N1 C10 C11 C12 178.99(17)
C4 C5 C11 C10 -178.2(2)
C6 C5 C11 C10 0.5(2)
C4 C5 C11 C12 2.4(4)
C6 C5 C11 C12 -179.0(2)
C10 C11 C12 C13 147.9(2)
C5 C11 C12 C13 -32.7(3)
C10 C11 C12 C19 25.3(3)
C5 C11 C12 C19 -155.3(2)
C11 C12 C13 C18 125.7(2)
C19 C12 C13 C18 -114.4(2)
C11 C12 C13 C14 -52.1(3)
C19 C12 C13 C14 67.8(3)
C18 C13 C14 C15 -0.1(3)
C12 C13 C14 C15 177.7(2)
C13 C14 C15 C16 -0.1(4)
C14 C15 C16 C17 0.6(4)
C15 C16 C17 C18 -1.1(4)
C14 C13 C18 C17 -0.4(3)
C12 C13 C18 C17 -178.2(2)
C16 C17 C18 C13 0.9(4)
C11 C12 C19 C20 -44.6(2)
C13 C12 C19 C20 -168.12(17)
C10 O3 C20 C21 168.87(17)
C10 O3 C20 C19 -15.5(3)
C12 C19 C20 C21 -142.3(2)
C12 C19 C20 O3 42.8(3)
O3 C20 C21 C22 175.27(18)
C19 C20 C21 C22 0.2(4)
C23 O5 C22 O4 1.5(3)
C23 O5 C22 C21 -178.92(16)
C20 C21 C22 O4 9.6(4)
C20 C21 C22 O5 -169.9(2)
C22 O5 C23 C24 -173.46(17)
|
1501977.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501977.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501977
loop_
_publ_author_name
'Emerson, Christopher R.'
'Zakharov, Lev N.'
'Blakemore, Paul R.'
_publ_section_title
;
Iterative stereospecific reagent-controlled homologation using a
functionalized \a-chloroalkyllithium: synthesis of cyclic targets related
to epibatidine.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1318
_journal_page_last 1321
_journal_paper_doi 10.1021/ol103170y
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C12 H16 O3 S'
_chemical_formula_weight 240.31
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXLTL
_cell_angle_alpha 90.00
_cell_angle_beta 99.583(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 7.8940(9)
_cell_length_b 5.7394(6)
_cell_length_c 13.2234(14)
_cell_measurement_reflns_used 5446
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 28.26
_cell_measurement_theta_min 2.62
_cell_volume 590.75(11)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_structure_solution 'Bruker SHELXTL'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker Apex CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0153
_diffrn_reflns_av_sigmaI/netI 0.0170
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 6641
_diffrn_reflns_theta_full 27.00
_diffrn_reflns_theta_max 27.00
_diffrn_reflns_theta_min 1.56
_exptl_absorpt_coefficient_mu 0.263
_exptl_absorpt_correction_T_max 0.9641
_exptl_absorpt_correction_T_min 0.9089
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.351
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 256
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.14
_refine_diff_density_max 0.203
_refine_diff_density_min -0.153
_refine_diff_density_rms 0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.08(5)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 209
_refine_ls_number_reflns 2579
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.053
_refine_ls_R_factor_all 0.0234
_refine_ls_R_factor_gt 0.0231
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.0627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0612
_refine_ls_wR_factor_ref 0.0615
_reflns_number_gt 2552
_reflns_number_total 2579
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103170y_si_003.cif
_cod_data_source_block pb29(R11)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_database_code 1501977
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
S1 S 0.26879(3) 0.82388(6) 0.25668(2) 0.02728(9) Uani 1 1 d
O1 O 0.41023(11) 0.63038(18) 0.59246(7) 0.0301(2) Uani 1 1 d
O2 O 0.11889(12) 0.58319(19) 0.56587(8) 0.0326(2) Uani 1 1 d
O3 O 0.42850(12) 0.69971(19) 0.23956(7) 0.0342(2) Uani 1 1 d
C1 C 0.24420(16) 0.7768(2) 0.38876(9) 0.0258(3) Uani 1 1 d
C2 C 0.27511(17) 0.5256(2) 0.42350(10) 0.0279(3) Uani 1 1 d
C3 C 0.27445(17) 0.4983(2) 0.53723(10) 0.0276(3) Uani 1 1 d
C4 C 0.34901(18) 0.7111(3) 0.68241(10) 0.0307(3) Uani 1 1 d
C5 C 0.16388(19) 0.7645(2) 0.64001(10) 0.0305(3) Uani 1 1 d
C6 C 0.09124(15) 0.6524(2) 0.19530(9) 0.0245(2) Uani 1 1 d
C7 C -0.07565(18) 0.7341(2) 0.19295(10) 0.0291(3) Uani 1 1 d
C8 C -0.21356(16) 0.6070(2) 0.14241(10) 0.0295(3) Uani 1 1 d
C9 C -0.18729(17) 0.3990(2) 0.09279(10) 0.0280(3) Uani 1 1 d
C10 C -0.01928(16) 0.3199(3) 0.09534(9) 0.0288(2) Uani 1 1 d
C11 C 0.11999(17) 0.4463(2) 0.14643(10) 0.0274(3) Uani 1 1 d
C12 C -0.3380(2) 0.2613(3) 0.03854(12) 0.0381(3) Uani 1 1 d
H1A H 0.1286(19) 0.826(4) 0.3960(11) 0.029(3) Uiso 1 1 d
H1B H 0.325(2) 0.874(3) 0.4247(12) 0.031(4) Uiso 1 1 d
H2A H 0.194(2) 0.433(4) 0.3861(14) 0.039(5) Uiso 1 1 d
H2B H 0.381(2) 0.474(3) 0.4103(12) 0.028(4) Uiso 1 1 d
H3 H 0.2837(18) 0.331(4) 0.5581(11) 0.031(4) Uiso 1 1 d
H4A H 0.425(2) 0.840(4) 0.7096(13) 0.042(4) Uiso 1 1 d
H4B H 0.3592(19) 0.585(3) 0.7290(11) 0.024(4) Uiso 1 1 d
H5A H 0.1533(18) 0.913(3) 0.6082(11) 0.017(3) Uiso 1 1 d
H5B H 0.095(2) 0.751(3) 0.6919(12) 0.032(4) Uiso 1 1 d
H7 H -0.088(2) 0.880(3) 0.2232(12) 0.029(4) Uiso 1 1 d
H8 H -0.322(2) 0.663(4) 0.1435(14) 0.043(5) Uiso 1 1 d
H10 H -0.0007(19) 0.177(3) 0.0628(11) 0.022(3) Uiso 1 1 d
H11 H 0.238(2) 0.396(3) 0.1495(13) 0.038(5) Uiso 1 1 d
H12A H -0.315(3) 0.102(6) 0.038(2) 0.096(10) Uiso 1 1 d
H12B H -0.435(2) 0.284(4) 0.0653(15) 0.050(5) Uiso 1 1 d
H12C H -0.365(3) 0.305(5) -0.0346(17) 0.065(6) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.02422(14) 0.02943(15) 0.02924(15) 0.00148(13) 0.00751(10) -0.00090(14)
O1 0.0230(4) 0.0391(5) 0.0288(4) -0.0033(4) 0.0061(3) -0.0023(4)
O2 0.0228(4) 0.0435(6) 0.0330(5) -0.0065(4) 0.0093(4) -0.0063(4)
O3 0.0228(4) 0.0465(6) 0.0353(5) -0.0014(5) 0.0108(4) 0.0004(4)
C1 0.0239(6) 0.0278(7) 0.0262(5) -0.0036(5) 0.0053(5) -0.0001(4)
C2 0.0274(6) 0.0283(6) 0.0290(6) -0.0034(5) 0.0075(5) 0.0001(5)
C3 0.0261(6) 0.0283(6) 0.0290(6) -0.0012(5) 0.0066(5) -0.0015(5)
C4 0.0297(7) 0.0366(7) 0.0266(6) -0.0018(6) 0.0067(5) -0.0027(6)
C5 0.0320(7) 0.0328(8) 0.0285(6) -0.0001(5) 0.0106(5) 0.0013(5)
C6 0.0235(6) 0.0280(6) 0.0224(5) 0.0013(4) 0.0049(4) 0.0002(5)
C7 0.0275(6) 0.0278(6) 0.0329(7) -0.0003(6) 0.0078(5) 0.0043(5)
C8 0.0231(6) 0.0351(7) 0.0306(6) 0.0034(6) 0.0052(5) 0.0052(5)
C9 0.0291(6) 0.0334(6) 0.0219(5) 0.0040(5) 0.0052(5) -0.0001(5)
C10 0.0331(6) 0.0302(6) 0.0239(5) -0.0009(6) 0.0072(4) 0.0030(7)
C11 0.0258(6) 0.0309(6) 0.0263(6) 0.0022(5) 0.0071(5) 0.0068(5)
C12 0.0332(8) 0.0467(10) 0.0334(7) -0.0027(6) 0.0022(6) -0.0040(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 C6 106.54(6)
O3 S1 C1 107.64(6)
C6 S1 C1 98.83(6)
C3 O1 C4 105.72(9)
C3 O2 C5 107.62(10)
C2 C1 S1 113.31(9)
C2 C1 H1A 110.6(12)
S1 C1 H1A 107.7(9)
C2 C1 H1B 111.0(10)
S1 C1 H1B 103.5(10)
H1A C1 H1B 110.5(15)
C3 C2 C1 111.82(10)
C3 C2 H2A 111.0(11)
C1 C2 H2A 109.1(12)
C3 C2 H2B 107.8(10)
C1 C2 H2B 110.3(10)
H2A C2 H2B 106.7(15)
O1 C3 O2 106.93(10)
O1 C3 C2 109.29(10)
O2 C3 C2 111.91(11)
O1 C3 H3 111.1(8)
O2 C3 H3 106.3(8)
C2 C3 H3 111.2(9)
O1 C4 C5 101.36(10)
O1 C4 H4A 106.2(10)
C5 C4 H4A 118.5(11)
O1 C4 H4B 106.8(9)
C5 C4 H4B 111.7(9)
H4A C4 H4B 110.9(14)
O2 C5 C4 102.81(11)
O2 C5 H5A 110.8(9)
C4 C5 H5A 110.9(9)
O2 C5 H5B 109.2(10)
C4 C5 H5B 110.4(10)
H5A C5 H5B 112.3(13)
C11 C6 C7 120.33(12)
C11 C6 S1 120.26(10)
C7 C6 S1 119.34(11)
C8 C7 C6 119.79(13)
C8 C7 H7 123.1(10)
C6 C7 H7 117.1(10)
C7 C8 C9 120.75(12)
C7 C8 H8 118.0(13)
C9 C8 H8 121.2(13)
C8 C9 C10 118.81(13)
C8 C9 C12 120.36(12)
C10 C9 C12 120.83(13)
C11 C10 C9 120.77(13)
C11 C10 H10 120.0(9)
C9 C10 H10 119.2(9)
C6 C11 C10 119.56(12)
C6 C11 H11 117.6(10)
C10 C11 H11 122.9(10)
C9 C12 H12A 112.4(17)
C9 C12 H12B 112.9(13)
H12A C12 H12B 109(2)
C9 C12 H12C 111.1(15)
H12A C12 H12C 104(2)
H12B C12 H12C 106.6(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4979(10)
S1 C6 1.7926(13)
S1 C1 1.8094(13)
O1 C3 1.4129(16)
O1 C4 1.4334(16)
O2 C3 1.4297(16)
O2 C5 1.4330(17)
C1 C2 1.5204(18)
C1 H1A 0.975(15)
C1 H1B 0.916(18)
C2 C3 1.5130(18)
C2 H2A 0.91(2)
C2 H2B 0.929(16)
C3 H3 1.00(2)
C4 C5 1.507(2)
C4 H4A 0.98(2)
C4 H4B 0.945(17)
C5 H5A 0.947(16)
C5 H5B 0.945(15)
C6 C11 1.3844(18)
C6 C7 1.3940(18)
C7 C8 1.386(2)
C7 H7 0.939(18)
C8 C9 1.394(2)
C8 H8 0.918(18)
C9 C10 1.3969(18)
C9 C12 1.507(2)
C10 C11 1.3943(19)
C10 H10 0.950(16)
C11 H11 0.972(17)
C12 H12A 0.93(4)
C12 H12B 0.904(19)
C12 H12C 0.99(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O3 S1 C1 C2 -44.70(11)
C6 S1 C1 C2 65.90(10)
S1 C1 C2 C3 173.19(9)
C4 O1 C3 O2 25.36(13)
C4 O1 C3 C2 146.69(11)
C5 O2 C3 O1 -0.97(13)
C5 O2 C3 C2 -120.61(11)
C1 C2 C3 O1 -62.42(14)
C1 C2 C3 O2 55.83(14)
C3 O1 C4 C5 -38.17(13)
C3 O2 C5 C4 -22.22(13)
O1 C4 C5 O2 36.68(13)
O3 S1 C6 C11 1.04(12)
C1 S1 C6 C11 -110.43(11)
O3 S1 C6 C7 -175.84(10)
C1 S1 C6 C7 72.69(11)
C11 C6 C7 C8 0.75(19)
S1 C6 C7 C8 177.63(10)
C6 C7 C8 C9 -0.7(2)
C7 C8 C9 C10 0.37(19)
C7 C8 C9 C12 179.66(13)
C8 C9 C10 C11 -0.06(19)
C12 C9 C10 C11 -179.36(12)
C7 C6 C11 C10 -0.45(19)
S1 C6 C11 C10 -177.30(10)
C9 C10 C11 C6 0.11(19)
|
1501978.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501978.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501978
loop_
_publ_author_name
'Emerson, Christopher R.'
'Zakharov, Lev N.'
'Blakemore, Paul R.'
_publ_section_title
;
Iterative stereospecific reagent-controlled homologation using a
functionalized \a-chloroalkyllithium: synthesis of cyclic targets related
to epibatidine.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1318
_journal_page_last 1321
_journal_paper_doi 10.1021/ol103170y
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C12 H15 Cl O3 S'
_chemical_formula_sum 'C12 H15 Cl O3 S'
_chemical_formula_weight 274.75
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXLTL
_cell_angle_alpha 90.00
_cell_angle_beta 107.309(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 6.8959(12)
_cell_length_b 9.5822(16)
_cell_length_c 10.2161(17)
_cell_measurement_reflns_used 5324
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 28.26
_cell_measurement_theta_min 2.98
_cell_volume 644.49(19)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_structure_solution 'Bruker SHELXTL'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker Apex CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0166
_diffrn_reflns_av_sigmaI/netI 0.0195
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 7197
_diffrn_reflns_theta_full 26.99
_diffrn_reflns_theta_max 26.99
_diffrn_reflns_theta_min 2.09
_exptl_absorpt_coefficient_mu 0.451
_exptl_absorpt_correction_T_max 0.9866
_exptl_absorpt_correction_T_min 0.8400
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.416
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 288
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.292
_refine_diff_density_min -0.186
_refine_diff_density_rms 0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.03(5)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.047
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 202
_refine_ls_number_reflns 2804
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.047
_refine_ls_R_factor_all 0.0256
_refine_ls_R_factor_gt 0.0252
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.0328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0689
_refine_ls_wR_factor_ref 0.0695
_reflns_number_gt 2764
_reflns_number_total 2804
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103170y_si_003.cif
_cod_data_source_block pb26(SsynH12)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_database_code 1501978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.80170(7) 0.93223(4) 0.73895(4) 0.03594(11) Uani 1 1 d .
S1 S 0.91776(6) 0.84286(4) 0.49225(4) 0.02686(10) Uani 1 1 d .
O1 O 0.91895(19) 0.69719(12) 0.54421(13) 0.0354(3) Uani 1 1 d .
O2 O 1.4755(2) 1.01028(15) 0.90795(15) 0.0477(4) Uani 1 1 d .
O3 O 1.23009(19) 1.16587(13) 0.80943(13) 0.0355(3) Uani 1 1 d .
C1 C 0.9742(2) 0.95818(16) 0.64116(16) 0.0260(3) Uani 1 1 d .
C2 C 1.1931(3) 0.9320(2) 0.72480(17) 0.0318(3) Uani 1 1 d .
C3 C 1.2632(3) 1.02523(19) 0.84871(18) 0.0327(3) Uani 1 1 d .
C4 C 1.5525(3) 1.1438(2) 0.9626(2) 0.0414(4) Uani 1 1 d .
C5 C 1.3718(3) 1.2411(2) 0.9175(2) 0.0387(4) Uani 1 1 d .
C6 C 0.6602(2) 0.89274(16) 0.41270(15) 0.0240(3) Uani 1 1 d .
C7 C 0.6201(2) 1.02754(17) 0.36182(17) 0.0281(3) Uani 1 1 d .
C8 C 0.4213(3) 1.06262(18) 0.28893(17) 0.0300(3) Uani 1 1 d .
C9 C 0.2656(3) 0.96382(18) 0.26489(17) 0.0300(3) Uani 1 1 d .
C10 C 0.3113(2) 0.8304(2) 0.31651(18) 0.0330(3) Uani 1 1 d .
C11 C 0.5081(3) 0.79300(18) 0.39107(18) 0.0308(3) Uani 1 1 d .
C12 C 0.0523(3) 1.0040(2) 0.1834(2) 0.0411(4) Uani 1 1 d .
H12A H -0.0377 0.9233 0.1758 0.062 Uiso 1 1 calc R
H12B H 0.0510 1.0344 0.0916 0.062 Uiso 1 1 calc R
H12C H 0.0050 1.0804 0.2300 0.062 Uiso 1 1 calc R
H1 H 0.964(3) 1.046(2) 0.610(2) 0.031(5) Uiso 1 1 d .
H2A H 1.288(3) 0.945(2) 0.673(2) 0.030(5) Uiso 1 1 d .
H2B H 1.208(3) 0.831(3) 0.755(2) 0.050(7) Uiso 1 1 d .
H3 H 1.208(3) 1.004(2) 0.912(2) 0.038(6) Uiso 1 1 d .
H4A H 1.674(3) 1.170(2) 0.929(2) 0.035(5) Uiso 1 1 d .
H4B H 1.596(3) 1.134(3) 1.059(2) 0.040(6) Uiso 1 1 d .
H5A H 1.414(3) 1.318(3) 0.883(2) 0.038(6) Uiso 1 1 d .
H5B H 1.320(3) 1.260(2) 0.984(2) 0.032(5) Uiso 1 1 d .
H7 H 0.737(4) 1.103(3) 0.371(2) 0.044(6) Uiso 1 1 d .
H8 H 0.388(3) 1.153(2) 0.2641(19) 0.024(4) Uiso 1 1 d .
H10 H 0.206(3) 0.754(3) 0.303(2) 0.042(6) Uiso 1 1 d .
H11 H 0.542(3) 0.699(2) 0.428(2) 0.029(5) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0401(2) 0.0361(2) 0.0389(2) -0.00785(17) 0.02277(17) -0.00844(17)
S1 0.02640(18) 0.02772(18) 0.02756(17) -0.00061(15) 0.00973(13) 0.00627(14)
O1 0.0415(7) 0.0242(5) 0.0373(6) -0.0010(5) 0.0070(5) 0.0092(5)
O2 0.0365(7) 0.0462(8) 0.0471(8) -0.0001(6) -0.0079(6) 0.0088(6)
O3 0.0344(6) 0.0307(6) 0.0341(6) -0.0009(5) -0.0013(5) 0.0019(5)
C1 0.0288(7) 0.0217(7) 0.0301(7) 0.0005(6) 0.0126(6) 0.0003(6)
C2 0.0303(8) 0.0290(7) 0.0343(8) -0.0001(7) 0.0068(6) 0.0037(7)
C3 0.0328(8) 0.0342(8) 0.0294(8) 0.0045(7) 0.0070(7) 0.0011(7)
C4 0.0339(9) 0.0531(11) 0.0317(9) 0.0009(8) 0.0015(7) -0.0048(8)
C5 0.0408(10) 0.0398(10) 0.0315(9) -0.0046(8) 0.0048(7) -0.0049(8)
C6 0.0230(7) 0.0237(7) 0.0265(7) -0.0004(5) 0.0093(6) 0.0043(5)
C7 0.0280(8) 0.0233(7) 0.0329(8) 0.0003(6) 0.0088(6) -0.0008(6)
C8 0.0288(8) 0.0266(8) 0.0328(8) 0.0000(6) 0.0063(6) 0.0046(6)
C9 0.0264(8) 0.0380(9) 0.0279(7) -0.0054(6) 0.0115(6) 0.0020(6)
C10 0.0294(8) 0.0347(9) 0.0387(8) -0.0041(7) 0.0158(6) -0.0079(7)
C11 0.0349(8) 0.0249(7) 0.0360(9) -0.0001(7) 0.0158(7) -0.0003(6)
C12 0.0256(8) 0.0573(12) 0.0386(9) -0.0061(9) 0.0068(7) 0.0036(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 C6 108.17(8)
O1 S1 C1 107.00(7)
C6 S1 C1 98.86(7)
C3 O2 C4 107.02(14)
C3 O3 C5 104.29(13)
C2 C1 Cl1 112.26(11)
C2 C1 S1 107.38(11)
Cl1 C1 S1 111.70(8)
C2 C1 H1 108.4(13)
Cl1 C1 H1 109.7(13)
S1 C1 H1 107.2(13)
C3 C2 C1 113.04(14)
C3 C2 H2A 106.6(13)
C1 C2 H2A 113.1(12)
C3 C2 H2B 109.5(14)
C1 C2 H2B 108.9(13)
H2A C2 H2B 105.4(18)
O3 C3 O2 106.18(14)
O3 C3 C2 110.16(14)
O2 C3 C2 109.36(15)
O3 C3 H3 111.8(15)
O2 C3 H3 106.5(15)
C2 C3 H3 112.5(16)
O2 C4 C5 104.77(15)
O2 C4 H4A 109.7(13)
C5 C4 H4A 115.1(13)
O2 C4 H4B 106.6(15)
C5 C4 H4B 110.8(14)
H4A C4 H4B 109.5(18)
O3 C5 C4 103.62(16)
O3 C5 H5A 109.9(15)
C4 C5 H5A 106.7(15)
O3 C5 H5B 111.1(15)
C4 C5 H5B 112.3(14)
H5A C5 H5B 113(2)
C11 C6 C7 121.59(15)
C11 C6 S1 119.40(12)
C7 C6 S1 118.69(12)
C6 C7 C8 118.65(15)
C6 C7 H7 122.4(14)
C8 C7 H7 118.8(13)
C7 C8 C9 120.87(16)
C7 C8 H8 120.1(12)
C9 C8 H8 118.7(12)
C10 C9 C8 118.91(15)
C10 C9 C12 121.34(16)
C8 C9 C12 119.75(16)
C9 C10 C11 121.41(16)
C9 C10 H10 122.9(14)
C11 C10 H10 115.7(14)
C6 C11 C10 118.56(16)
C6 C11 H11 119.5(12)
C10 C11 H11 122.0(12)
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7841(16)
S1 O1 1.4925(13)
S1 C6 1.7843(16)
S1 C1 1.8260(16)
O2 C3 1.415(2)
O2 C4 1.433(3)
O3 C3 1.405(2)
O3 C5 1.432(2)
C1 C2 1.518(2)
C1 H1 0.90(2)
C2 C3 1.507(3)
C2 H2A 0.96(2)
C2 H2B 1.01(3)
C3 H3 0.87(2)
C4 C5 1.515(3)
C4 H4A 1.02(2)
C4 H4B 0.95(2)
C5 H5A 0.90(3)
C5 H5B 0.87(2)
C6 C11 1.387(2)
C6 C7 1.389(2)
C7 C8 1.393(2)
C7 H7 1.06(3)
C8 C9 1.397(2)
C8 H8 0.91(2)
C9 C10 1.383(3)
C9 C12 1.509(2)
C10 C11 1.391(2)
C10 H10 1.01(2)
C11 H11 0.98(2)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 C1 C2 68.01(12)
C6 S1 C1 C2 -179.79(11)
O1 S1 C1 Cl1 -55.47(10)
C6 S1 C1 Cl1 56.72(10)
Cl1 C1 C2 C3 -59.25(17)
S1 C1 C2 C3 177.61(13)
C5 O3 C3 O2 -38.41(19)
C5 O3 C3 C2 -156.73(16)
C4 O2 C3 O3 27.25(19)
C4 O2 C3 C2 146.09(16)
C1 C2 C3 O3 -54.3(2)
C1 C2 C3 O2 -170.63(14)
C3 O2 C4 C5 -5.7(2)
C3 O3 C5 C4 33.58(19)
O2 C4 C5 O3 -17.1(2)
O1 S1 C6 C11 -9.30(15)
C1 S1 C6 C11 -120.56(13)
O1 S1 C6 C7 177.04(12)
C1 S1 C6 C7 65.78(14)
C11 C6 C7 C8 0.8(2)
S1 C6 C7 C8 174.30(12)
C6 C7 C8 C9 -1.2(2)
C7 C8 C9 C10 0.9(2)
C7 C8 C9 C12 -178.91(16)
C8 C9 C10 C11 -0.2(2)
C12 C9 C10 C11 179.68(15)
C7 C6 C11 C10 0.0(2)
S1 C6 C11 C10 -173.51(12)
C9 C10 C11 C6 -0.3(2)
|
1501979.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501979.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501979
loop_
_publ_author_name
'Emerson, Christopher R.'
'Zakharov, Lev N.'
'Blakemore, Paul R.'
_publ_section_title
;
Iterative stereospecific reagent-controlled homologation using a
functionalized \a-chloroalkyllithium: synthesis of cyclic targets related
to epibatidine.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1318
_journal_page_last 1321
_journal_paper_doi 10.1021/ol103170y
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C12 H15 Cl O3 S'
_chemical_formula_weight 274.75
_chemical_name_systematic
;
?
;
_space_group_IT_number 5
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'C 2y'
_symmetry_space_group_name_H-M 'C 1 2 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXLTL
_cell_angle_alpha 90.00
_cell_angle_beta 94.396(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 15.176(2)
_cell_length_b 9.6244(15)
_cell_length_c 8.8976(14)
_cell_measurement_reflns_used 4957
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 28.19
_cell_measurement_theta_min 2.51
_cell_volume 1295.8(3)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_structure_solution 'Bruker SHELXTL'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker Apex CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0222
_diffrn_reflns_av_sigmaI/netI 0.0277
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 7327
_diffrn_reflns_theta_full 26.99
_diffrn_reflns_theta_max 26.99
_diffrn_reflns_theta_min 2.30
_exptl_absorpt_coefficient_mu 0.449
_exptl_absorpt_correction_T_max 0.9077
_exptl_absorpt_correction_T_min 0.8338
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.408
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 576
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.22
_refine_diff_density_max 0.733
_refine_diff_density_min -0.234
_refine_diff_density_rms 0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.07(7)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.081
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 182
_refine_ls_number_reflns 2834
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.081
_refine_ls_R_factor_all 0.0398
_refine_ls_R_factor_gt 0.0394
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0751P)^2^+0.2741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1093
_refine_ls_wR_factor_ref 0.1100
_reflns_number_gt 2790
_reflns_number_total 2834
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103170y_si_003.cif
_cod_data_source_block pbr27(SantiD12)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1295.7(3)
_cod_original_sg_symbol_H-M C2
_cod_database_code 1501979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.39366(4) 0.52084(7) 0.49453(7) 0.0498(2) Uani 1 1 d .
S1 S 0.20858(3) 0.55011(6) 0.52162(5) 0.03667(15) Uani 1 1 d .
O1 O 0.34718(19) 0.6783(3) 0.0271(3) 0.0707(6) Uani 1 1 d .
O2 O 0.33512(19) 0.4524(3) 0.0825(3) 0.0671(6) Uani 1 1 d .
O3 O 0.22212(12) 0.6963(2) 0.5713(2) 0.0502(5) Uani 1 1 d .
C1 C 0.28966(13) 0.5165(3) 0.3838(2) 0.0368(5) Uani 1 1 d .
C2 C 0.28950(17) 0.6196(3) 0.2577(3) 0.0394(5) Uani 1 1 d .
C3 C 0.35595(17) 0.5816(3) 0.1446(3) 0.0507(7) Uani 1 1 d .
H3A H 0.4175 0.5822 0.1936 0.061 Uiso 1 1 calc R
C4 C 0.3707(2) 0.6060(5) -0.1024(4) 0.0652(9) Uani 1 1 d .
H4A H 0.4322 0.6281 -0.1238 0.078 Uiso 1 1 calc R
H4B H 0.3308 0.6316 -0.1914 0.078 Uiso 1 1 calc R
C5 C 0.3618(3) 0.4563(4) -0.0669(4) 0.0720(10) Uani 1 1 d .
H5A H 0.3168 0.4119 -0.1378 0.086 Uiso 1 1 calc R
H5B H 0.4188 0.4076 -0.0732 0.086 Uiso 1 1 calc R
C6 C 0.11199(13) 0.5465(3) 0.3929(2) 0.0343(4) Uani 1 1 d .
C7 C 0.07765(18) 0.4214(3) 0.3403(4) 0.0449(6) Uani 1 1 d .
C8 C 0.00122(19) 0.4224(3) 0.2434(4) 0.0513(7) Uani 1 1 d .
C9 C -0.04131(13) 0.5439(3) 0.2009(2) 0.0418(5) Uani 1 1 d .
C10 C -0.00663(17) 0.6692(3) 0.2592(3) 0.0455(6) Uani 1 1 d .
C11 C 0.06994(17) 0.6704(3) 0.3546(3) 0.0429(6) Uani 1 1 d .
C12 C -0.12318(16) 0.5449(4) 0.0941(3) 0.0563(7) Uani 1 1 d .
H12A H -0.1385 0.4494 0.0641 0.084 Uiso 1 1 calc R
H12B H -0.1122 0.5995 0.0044 0.084 Uiso 1 1 calc R
H12C H -0.1721 0.5864 0.1441 0.084 Uiso 1 1 calc R
D1 H 0.2784(17) 0.413(3) 0.350(3) 0.026(6) Uiso 1 1 d .
H2A H 0.2279(19) 0.613(3) 0.206(3) 0.044(7) Uiso 1 1 d .
H2B H 0.300(2) 0.716(4) 0.298(4) 0.057(9) Uiso 1 1 d .
H7 H 0.104(3) 0.351(4) 0.365(5) 0.064(11) Uiso 1 1 d .
H8 H -0.025(3) 0.343(4) 0.216(5) 0.065(11) Uiso 1 1 d .
H10 H -0.043(3) 0.754(5) 0.238(5) 0.074(11) Uiso 1 1 d .
H11 H 0.089(2) 0.761(3) 0.392(4) 0.044(8) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0340(3) 0.0648(4) 0.0487(3) 0.0034(3) -0.0101(2) 0.0017(3)
S1 0.0342(3) 0.0463(3) 0.0289(2) -0.0020(2) -0.00144(17) -0.0005(2)
O1 0.0995(18) 0.0680(14) 0.0462(12) 0.0012(10) 0.0158(12) -0.0158(13)
O2 0.0854(17) 0.0597(12) 0.0589(13) -0.0040(10) 0.0223(12) 0.0072(11)
O3 0.0434(9) 0.0568(11) 0.0486(10) -0.0205(9) -0.0072(8) 0.0035(8)
C1 0.0274(9) 0.0489(13) 0.0333(10) -0.0009(9) -0.0034(7) 0.0026(9)
C2 0.0428(12) 0.0397(12) 0.0350(12) -0.0002(9) -0.0011(9) 0.0003(10)
C3 0.0397(13) 0.074(2) 0.0383(12) 0.0014(12) 0.0027(9) -0.0104(12)
C4 0.0438(15) 0.111(3) 0.0404(14) 0.0054(15) 0.0024(11) -0.0124(16)
C5 0.0531(18) 0.095(3) 0.068(2) -0.030(2) 0.0025(15) 0.0098(17)
C6 0.0302(9) 0.0423(11) 0.0303(9) 0.0001(10) 0.0026(7) 0.0001(10)
C7 0.0404(13) 0.0385(13) 0.0549(16) 0.0011(11) -0.0032(12) -0.0014(11)
C8 0.0431(14) 0.0519(16) 0.0578(17) -0.0086(12) -0.0039(12) -0.0096(12)
C9 0.0286(9) 0.0632(15) 0.0339(9) -0.0005(12) 0.0050(7) 0.0003(11)
C10 0.0361(12) 0.0522(14) 0.0479(15) -0.0017(11) 0.0005(10) 0.0065(11)
C11 0.0372(12) 0.0412(12) 0.0496(14) -0.0096(11) -0.0021(10) 0.0033(10)
C12 0.0333(11) 0.089(2) 0.0457(12) -0.0078(16) -0.0009(9) -0.0019(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 C6 107.26(11)
O3 S1 C1 106.38(12)
C6 S1 C1 97.33(9)
C3 O1 C4 105.5(3)
C3 O2 C5 106.1(3)
C2 C1 Cl1 110.29(17)
C2 C1 S1 114.97(17)
Cl1 C1 S1 103.64(11)
C2 C1 D1 114.9(15)
Cl1 C1 D1 107.2(15)
S1 C1 D1 104.9(13)
C1 C2 C3 111.9(2)
C1 C2 H2A 104.1(17)
C3 C2 H2A 108.6(16)
C1 C2 H2B 111(2)
C3 C2 H2B 111(2)
H2A C2 H2B 110(3)
O2 C3 O1 107.0(2)
O2 C3 C2 109.6(2)
O1 C3 C2 107.7(2)
O2 C3 H3A 110.8
O1 C3 H3A 110.8
C2 C3 H3A 110.8
O1 C4 C5 105.7(3)
O1 C4 H4A 110.6
C5 C4 H4A 110.6
O1 C4 H4B 110.6
C5 C4 H4B 110.6
H4A C4 H4B 108.7
O2 C5 C4 105.2(3)
O2 C5 H5A 110.7
C4 C5 H5A 110.7
O2 C5 H5B 110.7
C4 C5 H5B 110.7
H5A C5 H5B 108.8
C7 C6 C11 120.9(2)
C7 C6 S1 120.2(2)
C11 C6 S1 118.77(19)
C6 C7 C8 118.6(3)
C6 C7 H7 118(3)
C8 C7 H7 123(3)
C9 C8 C7 121.9(3)
C9 C8 H8 118(3)
C7 C8 H8 120(3)
C8 C9 C10 118.4(2)
C8 C9 C12 121.8(3)
C10 C9 C12 119.8(3)
C11 C10 C9 120.6(2)
C11 C10 H10 122(3)
C9 C10 H10 117(3)
C6 C11 C10 119.6(2)
C6 C11 H11 124.7(19)
C10 C11 H11 115.8(19)
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.796(2)
S1 O3 1.484(2)
S1 C6 1.790(2)
S1 C1 1.831(2)
O1 C3 1.398(4)
O1 C4 1.415(4)
O2 C3 1.388(4)
O2 C5 1.420(5)
C1 C2 1.498(3)
C1 D1 1.05(3)
C2 C3 1.523(3)
C2 H2A 1.01(3)
C2 H2B 1.01(4)
C3 H3A 1.0000
C4 C5 1.484(6)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.380(4)
C6 C11 1.383(4)
C7 C8 1.391(4)
C7 H7 0.81(4)
C8 C9 1.375(4)
C8 H8 0.89(4)
C9 C10 1.399(4)
C9 C12 1.505(3)
C10 C11 1.386(4)
C10 H10 1.00(4)
C11 H11 0.97(3)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O3 S1 C1 C2 -52.3(2)
C6 S1 C1 C2 58.1(2)
O3 S1 C1 Cl1 68.11(14)
C6 S1 C1 Cl1 178.57(12)
Cl1 C1 C2 C3 65.6(2)
S1 C1 C2 C3 -177.71(17)
C5 O2 C3 O1 31.7(3)
C5 O2 C3 C2 148.3(3)
C4 O1 C3 O2 -32.3(3)
C4 O1 C3 C2 -150.2(2)
C1 C2 C3 O2 60.2(3)
C1 C2 C3 O1 176.4(2)
C3 O1 C4 C5 19.8(4)
C3 O2 C5 C4 -18.4(4)
O1 C4 C5 O2 -1.0(4)
O3 S1 C6 C7 -173.1(2)
C1 S1 C6 C7 77.2(2)
O3 S1 C6 C11 3.3(2)
C1 S1 C6 C11 -106.5(2)
C11 C6 C7 C8 2.1(4)
S1 C6 C7 C8 178.4(2)
C6 C7 C8 C9 -0.9(4)
C7 C8 C9 C10 -0.9(4)
C7 C8 C9 C12 179.0(3)
C8 C9 C10 C11 1.5(4)
C12 C9 C10 C11 -178.3(2)
C7 C6 C11 C10 -1.5(3)
S1 C6 C11 C10 -177.80(19)
C9 C10 C11 C6 -0.3(4)
|
1501980.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501980.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501980
loop_
_publ_author_name
'Emerson, Christopher R.'
'Zakharov, Lev N.'
'Blakemore, Paul R.'
_publ_section_title
;
Iterative stereospecific reagent-controlled homologation using a
functionalized \a-chloroalkyllithium: synthesis of cyclic targets related
to epibatidine.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1318
_journal_page_last 1321
_journal_paper_doi 10.1021/ol103170y
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C15 H20 Cl N O5'
_chemical_formula_sum 'C15 H20 Cl N O5'
_chemical_formula_weight 329.77
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXLTL
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.0356(7)
_cell_length_b 11.0921(10)
_cell_length_c 17.5466(16)
_cell_measurement_reflns_used 9194
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 28.12
_cell_measurement_theta_min 2.17
_cell_volume 1564.0(2)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'Bruker SHELXTL'
_computing_structure_solution 'Bruker SHELXTL'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker Apex CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0179
_diffrn_reflns_av_sigmaI/netI 0.0133
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 17516
_diffrn_reflns_theta_full 26.98
_diffrn_reflns_theta_max 26.98
_diffrn_reflns_theta_min 2.17
_exptl_absorpt_coefficient_mu 0.267
_exptl_absorpt_correction_T_max 0.9635
_exptl_absorpt_correction_T_min 0.9029
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.401
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 696
_exptl_crystal_size_max 0.39
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.14
_refine_diff_density_max 0.271
_refine_diff_density_min -0.151
_refine_diff_density_rms 0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.00(4)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 279
_refine_ls_number_reflns 3419
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.040
_refine_ls_R_factor_all 0.0300
_refine_ls_R_factor_gt 0.0291
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0777
_refine_ls_wR_factor_ref 0.0788
_reflns_number_gt 3324
_reflns_number_total 3419
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103170y_si_003.cif
_cod_data_source_block pb28(RRDD17)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1501980
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl 0.67634(4) 0.28942(3) 0.84934(2) 0.03296(10) Uani 1 1 d
O1 O -0.20465(13) 0.63303(11) 0.83822(6) 0.0352(2) Uani 1 1 d
O2 O 0.05023(16) 0.70878(11) 1.04174(6) 0.0381(2) Uani 1 1 d
O3 O -0.02361(16) 0.51622(10) 1.01891(6) 0.0390(3) Uani 1 1 d
O4 O -0.08393(15) 0.45212(10) 0.58318(6) 0.0363(3) Uani 1 1 d
O5 O 0.04547(18) 0.62367(11) 0.61518(6) 0.0454(3) Uani 1 1 d
N1 N 0.50418(14) 0.47792(11) 0.80721(7) 0.0278(2) Uani 1 1 d
C1 C 0.49112(17) 0.36330(13) 0.82812(7) 0.0259(3) Uani 1 1 d
C2 C 0.34316(18) 0.30088(13) 0.83407(10) 0.0342(3) Uani 1 1 d
C3 C 0.19827(19) 0.36194(13) 0.81680(9) 0.0327(3) Uani 1 1 d
C4 C 0.20479(17) 0.48268(12) 0.79447(7) 0.0248(3) Uani 1 1 d
C5 C 0.36130(17) 0.53516(13) 0.79082(8) 0.0271(3) Uani 1 1 d
C6 C 0.04830(17) 0.55488(12) 0.77882(8) 0.0250(3) Uani 1 1 d
C7 C -0.05377(17) 0.56963(12) 0.85325(8) 0.0266(3) Uani 1 1 d
C8 C 0.04164(19) 0.64264(13) 0.91231(8) 0.0299(3) Uani 1 1 d
C9 C -0.03801(19) 0.63515(13) 0.98986(8) 0.0295(3) Uani 1 1 d
C10 C 0.0088(2) 0.66049(16) 1.11442(9) 0.0377(3) Uani 1 1 d
C11 C -0.0072(2) 0.52645(15) 1.09974(8) 0.0348(3) Uani 1 1 d
C12 C -0.05830(17) 0.49783(13) 0.71565(8) 0.0277(3) Uani 1 1 d
C13 C 0.02117(18) 0.50324(14) 0.63839(8) 0.0304(3) Uani 1 1 d
C14 C -0.0331(3) 0.5037(2) 0.51236(10) 0.0482(4) Uani 1 1 d
C15 C 0.0523(4) 0.6191(2) 0.53341(10) 0.0637(7) Uani 1 1 d
H1O H -0.274(3) 0.579(2) 0.8297(14) 0.061(7) Uiso 1 1 d
H2 H 0.342(2) 0.2147(18) 0.8511(10) 0.040(5) Uiso 1 1 d
H3 H 0.091(2) 0.3201(16) 0.8236(11) 0.038(5) Uiso 1 1 d
H5 H 0.373(2) 0.6203(16) 0.7760(9) 0.026(4) Uiso 1 1 d
D6 H 0.0767(19) 0.6345(14) 0.7629(8) 0.015(3) Uiso 1 1 d
D7 H -0.0787(18) 0.4874(13) 0.8750(8) 0.014(3) Uiso 1 1 d
H8A H 0.152(3) 0.6122(18) 0.9158(11) 0.044(5) Uiso 1 1 d
H8B H 0.046(2) 0.7215(17) 0.8961(10) 0.030(4) Uiso 1 1 d
H9 H -0.154(2) 0.6549(15) 0.9901(9) 0.024(4) Uiso 1 1 d
H10A H -0.099(3) 0.696(2) 1.1339(14) 0.060(7) Uiso 1 1 d
H10B H 0.099(3) 0.6828(17) 1.1460(12) 0.041(5) Uiso 1 1 d
H11A H -0.106(3) 0.4900(18) 1.1234(12) 0.047(6) Uiso 1 1 d
H11B H 0.092(3) 0.4848(18) 1.1173(12) 0.043(5) Uiso 1 1 d
H12A H -0.088(2) 0.4131(17) 0.7280(11) 0.036(5) Uiso 1 1 d
H12B H -0.168(2) 0.5420(15) 0.7106(10) 0.031(4) Uiso 1 1 d
H13 H 0.123(3) 0.4574(18) 0.6379(11) 0.040(5) Uiso 1 1 d
H14A H 0.036(3) 0.450(3) 0.4918(17) 0.080(9) Uiso 1 1 d
H14B H -0.140(4) 0.522(3) 0.4861(15) 0.074(8) Uiso 1 1 d
H15A H 0.185(6) 0.621(4) 0.518(2) 0.154(16) Uiso 1 1 d
H15B H -0.025(3) 0.687(2) 0.5158(17) 0.082(9) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.02717(16) 0.03235(16) 0.03935(18) -0.00219(14) -0.00435(14) 0.00804(13)
O1 0.0258(5) 0.0394(6) 0.0404(6) -0.0070(5) -0.0027(4) 0.0050(5)
O2 0.0546(6) 0.0333(5) 0.0263(5) -0.0013(4) -0.0049(5) -0.0119(5)
O3 0.0574(7) 0.0289(5) 0.0307(5) -0.0008(4) 0.0030(5) -0.0055(5)
O4 0.0457(6) 0.0384(6) 0.0246(5) -0.0023(4) -0.0043(5) -0.0116(5)
O5 0.0656(8) 0.0447(6) 0.0261(5) 0.0014(5) -0.0032(5) -0.0271(6)
N1 0.0241(6) 0.0298(6) 0.0296(6) -0.0001(5) -0.0013(4) -0.0002(5)
C1 0.0242(6) 0.0275(6) 0.0258(6) -0.0029(5) -0.0034(5) 0.0049(5)
C2 0.0308(7) 0.0247(6) 0.0469(8) 0.0014(6) -0.0053(6) 0.0004(6)
C3 0.0263(7) 0.0290(7) 0.0427(8) 0.0019(6) -0.0052(6) -0.0039(6)
C4 0.0247(6) 0.0276(6) 0.0220(6) -0.0016(5) -0.0019(5) 0.0010(5)
C5 0.0252(6) 0.0289(7) 0.0273(6) 0.0025(5) -0.0009(5) 0.0009(5)
C6 0.0229(6) 0.0268(6) 0.0253(6) 0.0005(5) -0.0017(5) -0.0014(5)
C7 0.0246(6) 0.0289(6) 0.0261(6) -0.0006(5) -0.0016(5) -0.0010(5)
C8 0.0311(7) 0.0300(7) 0.0287(7) -0.0002(5) -0.0008(6) -0.0058(6)
C9 0.0301(7) 0.0299(7) 0.0285(7) -0.0036(5) -0.0011(5) -0.0018(6)
C10 0.0460(9) 0.0408(8) 0.0265(6) -0.0009(6) -0.0006(7) -0.0019(7)
C11 0.0337(8) 0.0404(8) 0.0304(7) 0.0042(6) 0.0010(6) -0.0010(7)
C12 0.0238(6) 0.0347(7) 0.0245(6) 0.0014(6) -0.0035(5) -0.0022(6)
C13 0.0263(6) 0.0376(7) 0.0273(7) -0.0016(6) -0.0018(5) -0.0005(6)
C14 0.0598(11) 0.0584(11) 0.0264(7) -0.0030(7) 0.0006(8) -0.0182(10)
C15 0.0993(18) 0.0650(13) 0.0266(8) 0.0087(8) -0.0086(10) -0.0373(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1O 104.3(17)
C9 O2 C10 104.03(12)
C9 O3 C11 106.88(11)
C13 O4 C14 105.47(12)
C13 O5 C15 105.09(13)
C1 N1 C5 116.38(12)
N1 C1 C2 124.72(13)
N1 C1 Cl1 116.28(11)
C2 C1 Cl1 119.00(11)
C3 C2 C1 117.64(13)
C3 C2 H2 121.6(11)
C1 C2 H2 120.8(11)
C2 C3 C4 120.02(14)
C2 C3 H3 118.7(11)
C4 C3 H3 121.2(11)
C5 C4 C3 116.71(13)
C5 C4 C6 121.46(12)
C3 C4 C6 121.76(12)
N1 C5 C4 124.52(13)
N1 C5 H5 115.5(10)
C4 C5 H5 120.0(10)
C4 C6 C12 112.05(11)
C4 C6 C7 109.99(11)
C12 C6 C7 110.85(11)
C4 C6 D6 110.1(9)
C12 C6 D6 107.6(9)
C7 C6 D6 106.0(9)
O1 C7 C8 106.96(11)
O1 C7 C6 110.24(12)
C8 C7 C6 111.29(12)
O1 C7 D7 110.3(8)
C8 C7 D7 108.8(8)
C6 C7 D7 109.2(8)
C9 C8 C7 111.82(12)
C9 C8 H8A 108.6(12)
C7 C8 H8A 108.9(12)
C9 C8 H8B 110.3(11)
C7 C8 H8B 108.3(11)
H8A C8 H8B 108.9(17)
O2 C9 O3 105.36(12)
O2 C9 C8 109.68(12)
O3 C9 C8 109.95(12)
O2 C9 H9 110.7(10)
O3 C9 H9 106.9(10)
C8 C9 H9 113.9(10)
O2 C10 C11 103.71(12)
O2 C10 H10A 110.9(14)
C11 C10 H10A 111.4(13)
O2 C10 H10B 104.4(13)
C11 C10 H10B 115.0(12)
H10A C10 H10B 110.9(18)
O3 C11 C10 104.75(12)
O3 C11 H11A 108.3(13)
C10 C11 H11A 113.7(12)
O3 C11 H11B 110.6(12)
C10 C11 H11B 110.0(12)
H11A C11 H11B 109.4(17)
C13 C12 C6 113.45(11)
C13 C12 H12A 109.8(11)
C6 C12 H12A 111.5(11)
C13 C12 H12B 105.8(10)
C6 C12 H12B 110.4(10)
H12A C12 H12B 105.4(15)
O4 C13 O5 105.46(12)
O4 C13 C12 110.56(12)
O5 C13 C12 110.97(12)
O4 C13 H13 107.0(11)
O5 C13 H13 112.3(12)
C12 C13 H13 110.4(12)
O4 C14 C15 104.98(14)
O4 C14 H14A 105.4(19)
C15 C14 H14A 112.6(19)
O4 C14 H14B 103.8(16)
C15 C14 H14B 109.6(17)
H14A C14 H14B 119(2)
O5 C15 C14 104.99(15)
O5 C15 H15A 107(2)
C14 C15 H15A 114(2)
O5 C15 H15B 104.7(17)
C14 C15 H15B 105.8(16)
H15A C15 H15B 120(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7393(14)
O1 C7 1.4263(17)
O1 H1O 0.84(3)
O2 C9 1.4137(18)
O2 C10 1.4226(19)
O3 C9 1.4189(18)
O3 C11 1.4289(18)
O4 C13 1.4047(18)
O4 C14 1.428(2)
O5 C13 1.4101(19)
O5 C15 1.437(2)
N1 C1 1.3274(19)
N1 C5 1.3432(18)
C1 C2 1.380(2)
C2 C3 1.381(2)
C2 H2 1.001(19)
C3 C4 1.396(2)
C3 H3 0.98(2)
C4 C5 1.3873(19)
C4 C6 1.5160(19)
C5 H5 0.984(17)
C6 C12 1.5372(19)
C6 C7 1.5508(19)
C6 D6 0.954(15)
C7 C8 1.522(2)
C7 D7 1.009(15)
C8 C9 1.506(2)
C8 H8A 0.95(2)
C8 H8B 0.920(18)
C9 H9 0.959(18)
C10 C11 1.514(2)
C10 H10A 1.01(2)
C10 H10B 0.94(2)
C11 H11A 0.98(2)
C11 H11B 0.97(2)
C12 C13 1.4997(19)
C12 H12A 0.994(19)
C12 H12B 1.011(19)
C13 H13 0.97(2)
C14 C15 1.499(3)
C14 H14A 0.89(3)
C14 H14B 1.00(3)
C15 H15A 1.10(4)
C15 H15B 1.02(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.84(3) 2.14(3) 2.9547(16) 165(2) 1_455
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 C2 -0.1(2)
C5 N1 C1 Cl1 -179.98(10)
N1 C1 C2 C3 0.2(2)
Cl1 C1 C2 C3 -179.96(13)
C1 C2 C3 C4 -0.2(2)
C2 C3 C4 C5 0.1(2)
C2 C3 C4 C6 -176.89(14)
C1 N1 C5 C4 0.0(2)
C3 C4 C5 N1 0.0(2)
C6 C4 C5 N1 176.96(13)
C5 C4 C6 C12 124.58(13)
C3 C4 C6 C12 -58.57(18)
C5 C4 C6 C7 -111.64(14)
C3 C4 C6 C7 65.21(17)
C4 C6 C7 O1 -177.51(11)
C12 C6 C7 O1 -53.04(14)
C4 C6 C7 C8 63.98(14)
C12 C6 C7 C8 -171.54(11)
O1 C7 C8 C9 71.93(15)
C6 C7 C8 C9 -167.61(12)
C10 O2 C9 O3 -39.95(16)
C10 O2 C9 C8 -158.24(13)
C11 O3 C9 O2 28.85(16)
C11 O3 C9 C8 146.97(12)
C7 C8 C9 O2 -177.22(12)
C7 C8 C9 O3 67.37(16)
C9 O2 C10 C11 34.49(16)
C9 O3 C11 C10 -6.96(17)
O2 C10 C11 O3 -16.96(17)
C4 C6 C12 C13 -68.05(15)
C7 C6 C12 C13 168.65(12)
C14 O4 C13 O5 37.04(17)
C14 O4 C13 C12 157.06(15)
C15 O5 C13 O4 -36.4(2)
C15 O5 C13 C12 -156.12(17)
C6 C12 C13 O4 -178.71(12)
C6 C12 C13 O5 -62.06(16)
C13 O4 C14 C15 -22.7(2)
C13 O5 C15 C14 21.3(3)
O4 C14 C15 O5 0.7(3)
|
1501981.cif | #------------------------------------------------------------------------------
#$Date: 2018-09-02 02:52:36 +0300 (Sun, 02 Sep 2018) $
#$Revision: 210334 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/19/1501981.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501981
loop_
_publ_author_name
'Luo, Yong'
'Pan, Xiaolin'
'Wu, Jie'
_publ_section_title
;
Efficient Synthesis of 5H-Cyclopenta[c]quinoline Derivatives via
Palladium-Catalyzed Domino Reactions of o-Alkynylhalobenzene with Amine
;
_journal_coden_ASTM ORLEF7
_journal_issue 5
_journal_name_full 'Organic Letters'
_journal_page_first 1150
_journal_page_last 1153
_journal_paper_doi 10.1021/ol103173v
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C35 H25 N'
_chemical_formula_weight 459.56
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 92.575(4)
_cell_angle_beta 99.847(4)
_cell_angle_gamma 95.085(4)
_cell_formula_units_Z 2
_cell_length_a 8.821(3)
_cell_length_b 11.131(4)
_cell_length_c 13.131(4)
_cell_measurement_reflns_used 987
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 26.731
_cell_measurement_theta_min 2.843
_cell_volume 1262.9(7)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0442
_diffrn_reflns_av_sigmaI/netI 0.0345
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 5722
_diffrn_reflns_theta_full 26.01
_diffrn_reflns_theta_max 26.01
_diffrn_reflns_theta_min 1.58
_exptl_absorpt_coefficient_mu 0.069
_exptl_absorpt_correction_T_max 0.9890
_exptl_absorpt_correction_T_min 0.9849
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.209
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 484
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.16
_refine_diff_density_max 0.362
_refine_diff_density_min -0.352
_refine_diff_density_rms 0.095
_refine_ls_extinction_coef 0.027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 326
_refine_ls_number_reflns 4815
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.018
_refine_ls_R_factor_all 0.0902
_refine_ls_R_factor_gt 0.0746
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1628P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2025
_refine_ls_wR_factor_ref 0.2227
_reflns_number_gt 3567
_reflns_number_total 4815
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol103173v_si_001.cif
_cod_data_source_block a01012c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_original_formula_sum 'C17.50 H12.50 N0.50'
_cod_database_code 1501981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.36677(18) 0.79656(14) 0.00484(12) 0.0474(4) Uani 1 1 d .
C1 C 0.2824(2) 0.82752(16) 0.08341(14) 0.0449(5) Uani 1 1 d .
C2 C 0.1378(2) 0.87153(18) 0.05690(16) 0.0527(5) Uani 1 1 d .
H2A H 0.0966 0.8786 -0.0124 0.063 Uiso 1 1 calc R
C3 C 0.0564(2) 0.90434(19) 0.13232(17) 0.0581(5) Uani 1 1 d .
H3A H -0.0393 0.9337 0.1137 0.070 Uiso 1 1 calc R
C4 C 0.1162(3) 0.8940(2) 0.23600(17) 0.0604(6) Uani 1 1 d .
H4A H 0.0616 0.9176 0.2869 0.073 Uiso 1 1 calc R
C5 C 0.2565(3) 0.84857(18) 0.26300(16) 0.0554(5) Uani 1 1 d .
H5A H 0.2951 0.8410 0.3327 0.067 Uiso 1 1 calc R
C6 C 0.3434(2) 0.81340(16) 0.18865(14) 0.0454(5) Uani 1 1 d .
C7 C 0.4907(2) 0.76226(16) 0.21370(14) 0.0459(5) Uani 1 1 d .
C8 C 0.5767(2) 0.73261(17) 0.30580(15) 0.0512(5) Uani 1 1 d .
C9 C 0.7144(2) 0.68340(17) 0.28105(16) 0.0528(5) Uani 1 1 d .
C10 C 0.8384(3) 0.6406(2) 0.34636(18) 0.0660(6) Uani 1 1 d .
H10A H 0.8406 0.6409 0.4174 0.079 Uiso 1 1 calc R
C11 C 0.9565(3) 0.5982(2) 0.3035(2) 0.0734(7) Uani 1 1 d .
H11A H 1.0397 0.5706 0.3464 0.088 Uiso 1 1 calc R
C12 C 0.9542(3) 0.5959(2) 0.1975(2) 0.0667(6) Uani 1 1 d .
H12A H 1.0356 0.5662 0.1708 0.080 Uiso 1 1 calc R
C13 C 0.8333(2) 0.63669(18) 0.13076(18) 0.0569(5) Uani 1 1 d .
H13A H 0.8323 0.6343 0.0598 0.068 Uiso 1 1 calc R
C14 C 0.7116(2) 0.68198(16) 0.17272(15) 0.0487(5) Uani 1 1 d .
C15 C 0.5688(2) 0.73179(15) 0.12827(14) 0.0442(4) Uani 1 1 d .
C16 C 0.5072(2) 0.74913(15) 0.02777(14) 0.0431(4) Uani 1 1 d .
C17 C 0.5872(2) 0.71611(16) -0.05947(14) 0.0453(4) Uani 1 1 d .
C18 C 0.6968(2) 0.79794(18) -0.08955(15) 0.0522(5) Uani 1 1 d .
H18A H 0.7131 0.8767 -0.0603 0.063 Uiso 1 1 calc R
C19 C 0.7817(3) 0.7626(2) -0.16275(17) 0.0606(6) Uani 1 1 d .
H19A H 0.8555 0.8178 -0.1822 0.073 Uiso 1 1 calc R
C20 C 0.7584(3) 0.6468(2) -0.20732(18) 0.0649(6) Uani 1 1 d .
H20A H 0.8168 0.6233 -0.2561 0.078 Uiso 1 1 calc R
C21 C 0.6473(3) 0.5653(2) -0.17892(18) 0.0665(6) Uani 1 1 d .
H21A H 0.6304 0.4870 -0.2090 0.080 Uiso 1 1 calc R
C22 C 0.5618(3) 0.60018(18) -0.10624(16) 0.0573(5) Uani 1 1 d .
H22A H 0.4863 0.5455 -0.0883 0.069 Uiso 1 1 calc R
C23 C 0.3018(2) 0.81577(17) -0.10175(14) 0.0458(5) Uani 1 1 d .
C24 C 0.3267(2) 0.92846(17) -0.14019(15) 0.0510(5) Uani 1 1 d .
H24A H 0.3888 0.9904 -0.0991 0.061 Uiso 1 1 calc R
C25 C 0.2583(3) 0.94799(19) -0.24024(16) 0.0576(5) Uani 1 1 d .
H25A H 0.2737 1.0241 -0.2654 0.069 Uiso 1 1 calc R
C26 C 0.1678(2) 0.8570(2) -0.30353(16) 0.0584(6) Uani 1 1 d .
C27 C 0.1463(3) 0.7444(2) -0.26394(16) 0.0613(6) Uani 1 1 d .
H27A H 0.0864 0.6819 -0.3056 0.074 Uiso 1 1 calc R
C28 C 0.2125(2) 0.72318(19) -0.16330(16) 0.0560(5) Uani 1 1 d .
H28A H 0.1967 0.6473 -0.1378 0.067 Uiso 1 1 calc R
C29 C 0.0949(4) 0.8783(3) -0.41360(19) 0.0913(9) Uani 1 1 d .
H29A H 0.0354 0.8056 -0.4451 0.137 Uiso 1 1 calc R
H29B H 0.1746 0.9007 -0.4526 0.137 Uiso 1 1 calc R
H29C H 0.0286 0.9421 -0.4128 0.137 Uiso 1 1 calc R
C30 C 0.5428(3) 0.74254(19) 0.41282(16) 0.0557(5) Uani 1 1 d .
C31 C 0.4519(4) 0.6543(3) 0.4501(2) 0.0957(10) Uani 1 1 d .
H31A H 0.4083 0.5873 0.4066 0.115 Uiso 1 1 calc R
C32 C 0.4235(5) 0.6621(3) 0.5502(2) 0.1067(11) Uani 1 1 d .
H32A H 0.3613 0.6008 0.5730 0.128 Uiso 1 1 calc R
C33 C 0.4856(3) 0.7581(3) 0.61528(19) 0.0787(8) Uani 1 1 d .
H33A H 0.4684 0.7625 0.6832 0.094 Uiso 1 1 calc R
C34 C 0.5712(5) 0.8458(3) 0.5808(2) 0.1100(12) Uani 1 1 d .
H34A H 0.6121 0.9132 0.6246 0.132 Uiso 1 1 calc R
C35 C 0.6010(4) 0.8389(3) 0.4806(2) 0.1028(12) Uani 1 1 d .
H35A H 0.6622 0.9017 0.4588 0.123 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0473(9) 0.0505(9) 0.0469(9) 0.0110(7) 0.0086(7) 0.0144(7)
C1 0.0462(10) 0.0398(9) 0.0509(10) 0.0094(7) 0.0108(8) 0.0094(8)
C2 0.0484(11) 0.0562(11) 0.0554(11) 0.0135(9) 0.0068(9) 0.0158(9)
C3 0.0492(11) 0.0584(12) 0.0719(14) 0.0134(10) 0.0162(10) 0.0183(10)
C4 0.0595(13) 0.0624(13) 0.0660(13) 0.0053(10) 0.0224(10) 0.0193(11)
C5 0.0616(12) 0.0549(11) 0.0522(11) 0.0056(9) 0.0113(9) 0.0150(10)
C6 0.0484(10) 0.0394(9) 0.0493(10) 0.0074(7) 0.0086(8) 0.0074(8)
C7 0.0470(10) 0.0419(9) 0.0485(10) 0.0076(8) 0.0053(8) 0.0065(8)
C8 0.0526(11) 0.0488(10) 0.0511(11) 0.0094(8) 0.0032(9) 0.0076(9)
C9 0.0519(11) 0.0451(10) 0.0593(12) 0.0093(8) 0.0008(9) 0.0069(9)
C10 0.0628(13) 0.0623(13) 0.0693(14) 0.0148(11) -0.0049(11) 0.0136(11)
C11 0.0593(14) 0.0675(14) 0.0898(18) 0.0179(12) -0.0080(12) 0.0212(12)
C12 0.0520(12) 0.0567(12) 0.0939(17) 0.0161(11) 0.0097(12) 0.0197(10)
C13 0.0499(11) 0.0482(10) 0.0739(13) 0.0099(9) 0.0090(10) 0.0121(9)
C14 0.0468(10) 0.0385(9) 0.0599(11) 0.0100(8) 0.0038(9) 0.0071(8)
C15 0.0433(10) 0.0391(9) 0.0510(10) 0.0077(7) 0.0073(8) 0.0072(8)
C16 0.0434(10) 0.0363(9) 0.0507(10) 0.0089(7) 0.0085(8) 0.0070(8)
C17 0.0437(10) 0.0450(9) 0.0476(10) 0.0090(7) 0.0048(8) 0.0108(8)
C18 0.0506(11) 0.0475(10) 0.0592(11) 0.0044(9) 0.0099(9) 0.0073(9)
C19 0.0517(12) 0.0645(13) 0.0694(13) 0.0132(10) 0.0179(10) 0.0072(10)
C20 0.0667(14) 0.0695(14) 0.0653(13) 0.0053(11) 0.0227(11) 0.0222(12)
C21 0.0814(16) 0.0510(12) 0.0696(14) -0.0032(10) 0.0176(12) 0.0151(11)
C22 0.0648(13) 0.0479(11) 0.0617(12) 0.0063(9) 0.0183(10) 0.0041(10)
C23 0.0436(10) 0.0505(10) 0.0460(10) 0.0107(8) 0.0092(8) 0.0135(8)
C24 0.0532(11) 0.0475(10) 0.0533(11) 0.0050(8) 0.0097(9) 0.0091(9)
C25 0.0626(13) 0.0563(11) 0.0591(12) 0.0199(9) 0.0146(10) 0.0181(10)
C26 0.0514(11) 0.0747(14) 0.0527(11) 0.0131(10) 0.0113(9) 0.0178(10)
C27 0.0546(12) 0.0711(14) 0.0549(12) 0.0013(10) 0.0040(9) 0.0007(11)
C28 0.0553(12) 0.0530(11) 0.0605(12) 0.0107(9) 0.0108(10) 0.0047(10)
C29 0.093(2) 0.119(2) 0.0593(14) 0.0206(14) -0.0029(13) 0.0219(18)
C30 0.0585(12) 0.0579(11) 0.0507(11) 0.0116(9) 0.0018(9) 0.0169(10)
C31 0.136(3) 0.0799(17) 0.0712(16) -0.0043(13) 0.0368(17) -0.0200(19)
C32 0.133(3) 0.108(2) 0.087(2) 0.0142(17) 0.0511(19) -0.008(2)
C33 0.0830(18) 0.103(2) 0.0549(13) 0.0118(13) 0.0087(12) 0.0371(16)
C34 0.152(3) 0.103(2) 0.0674(17) -0.0197(16) 0.0170(19) -0.012(2)
C35 0.145(3) 0.091(2) 0.0638(15) -0.0085(14) 0.0208(17) -0.037(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 N1 C1 121.59(15)
C16 N1 C23 120.07(15)
C1 N1 C23 118.35(16)
C2 C1 C6 119.78(18)
C2 C1 N1 119.98(17)
C6 C1 N1 120.24(17)
C3 C2 C1 120.61(18)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C2 C3 C4 120.4(2)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
C5 C4 C3 119.6(2)
C5 C4 H4A 120.2
C3 C4 H4A 120.2
C4 C5 C6 122.0(2)
C4 C5 H5A 119.0
C6 C5 H5A 119.0
C5 C6 C1 117.61(19)
C5 C6 C7 123.75(18)
C1 C6 C7 118.64(18)
C8 C7 C15 109.58(18)
C8 C7 C6 132.90(19)
C15 C7 C6 117.51(16)
C7 C8 C9 107.25(17)
C7 C8 C30 129.7(2)
C9 C8 C30 122.99(18)
C10 C9 C14 120.2(2)
C10 C9 C8 130.0(2)
C14 C9 C8 109.85(18)
C11 C10 C9 118.8(2)
C11 C10 H10A 120.6
C9 C10 H10A 120.6
C10 C11 C12 121.4(2)
C10 C11 H11A 119.3
C12 C11 H11A 119.3
C13 C12 C11 121.3(2)
C13 C12 H12A 119.3
C11 C12 H12A 119.3
C12 C13 C14 118.5(2)
C12 C13 H13A 120.7
C14 C13 H13A 120.7
C13 C14 C9 119.80(19)
C13 C14 C15 134.01(19)
C9 C14 C15 106.18(17)
C16 C15 C7 121.95(17)
C16 C15 C14 130.91(18)
C7 C15 C14 107.13(16)
C15 C16 N1 120.04(17)
C15 C16 C17 121.55(17)
N1 C16 C17 118.41(16)
C22 C17 C18 118.95(19)
C22 C17 C16 120.37(17)
C18 C17 C16 120.50(16)
C19 C18 C17 120.11(18)
C19 C18 H18A 119.9
C17 C18 H18A 119.9
C20 C19 C18 120.7(2)
C20 C19 H19A 119.6
C18 C19 H19A 119.6
C19 C20 C21 119.4(2)
C19 C20 H20A 120.3
C21 C20 H20A 120.3
C22 C21 C20 120.10(19)
C22 C21 H21A 120.0
C20 C21 H21A 120.0
C21 C22 C17 120.7(2)
C21 C22 H22A 119.7
C17 C22 H22A 119.7
C28 C23 C24 120.35(18)
C28 C23 N1 119.99(17)
C24 C23 N1 119.64(16)
C25 C24 C23 119.42(18)
C25 C24 H24A 120.3
C23 C24 H24A 120.3
C26 C25 C24 121.48(19)
C26 C25 H25A 119.3
C24 C25 H25A 119.3
C25 C26 C27 118.10(19)
C25 C26 C29 121.3(2)
C27 C26 C29 120.6(2)
C26 C27 C28 121.38(19)
C26 C27 H27A 119.3
C28 C27 H27A 119.3
C23 C28 C27 119.25(19)
C23 C28 H28A 120.4
C27 C28 H28A 120.4
C26 C29 H29A 109.5
C26 C29 H29B 109.5
H29A C29 H29B 109.5
C26 C29 H29C 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
C35 C30 C31 115.7(2)
C35 C30 C8 122.4(2)
C31 C30 C8 121.8(2)
C30 C31 C32 121.9(3)
C30 C31 H31A 119.1
C32 C31 H31A 119.1
C33 C32 C31 120.5(3)
C33 C32 H32A 119.8
C31 C32 H32A 119.8
C34 C33 C32 119.0(3)
C34 C33 H33A 120.5
C32 C33 H33A 120.5
C33 C34 C35 121.1(3)
C33 C34 H34A 119.4
C35 C34 H34A 119.4
C30 C35 C34 121.8(3)
C30 C35 H35A 119.1
C34 C35 H35A 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C16 1.381(2)
N1 C1 1.419(2)
N1 C23 1.452(2)
C1 C2 1.401(3)
C1 C6 1.415(3)
C2 C3 1.374(3)
C2 H2A 0.9300
C3 C4 1.387(3)
C3 H3A 0.9300
C4 C5 1.375(3)
C4 H4A 0.9300
C5 C6 1.403(3)
C5 H5A 0.9300
C6 C7 1.457(3)
C7 C8 1.383(3)
C7 C15 1.456(3)
C8 C9 1.456(3)
C8 C30 1.487(3)
C9 C10 1.402(3)
C9 C14 1.418(3)
C10 C11 1.374(4)
C10 H10A 0.9300
C11 C12 1.388(4)
C11 H11A 0.9300
C12 C13 1.384(3)
C12 H12A 0.9300
C13 C14 1.408(3)
C13 H13A 0.9300
C14 C15 1.462(3)
C15 C16 1.368(3)
C16 C17 1.493(3)
C17 C22 1.387(3)
C17 C18 1.388(3)
C18 C19 1.380(3)
C18 H18A 0.9300
C19 C20 1.375(3)
C19 H19A 0.9300
C20 C21 1.386(3)
C20 H20A 0.9300
C21 C22 1.376(3)
C21 H21A 0.9300
C22 H22A 0.9300
C23 C28 1.378(3)
C23 C24 1.387(3)
C24 C25 1.384(3)
C24 H24A 0.9300
C25 C26 1.381(3)
C25 H25A 0.9300
C26 C27 1.388(3)
C26 C29 1.516(3)
C27 C28 1.390(3)
C27 H27A 0.9300
C28 H28A 0.9300
C29 H29A 0.9600
C29 H29B 0.9600
C29 H29C 0.9600
C30 C35 1.366(3)
C30 C31 1.373(3)
C31 C32 1.380(4)
C31 H31A 0.9300
C32 C33 1.351(4)
C32 H32A 0.9300
C33 C34 1.325(4)
C33 H33A 0.9300
C34 C35 1.385(4)
C34 H34A 0.9300
C35 H35A 0.9300
|
1501982.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501982.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501982
loop_
_publ_author_name
'Zhang, Xiu-Chun'
'Cao, Shu-Hua'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
Phosphine- and nitrogen-containing Lewis base catalyzed highly
regioselective and geometric selective cyclization of isatin derived
electron-deficient alkenes with ethyl 2,3-butadienoate.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1142
_journal_page_last 1145
_journal_paper_doi 10.1021/ol1031798
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C28 H29 N O7'
_chemical_formula_weight 491.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 92.115(3)
_cell_angle_beta 99.658(3)
_cell_angle_gamma 95.354(3)
_cell_formula_units_Z 2
_cell_length_a 8.9387(15)
_cell_length_b 9.9381(16)
_cell_length_c 14.389(2)
_cell_measurement_reflns_used 2464
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 55.243
_cell_measurement_theta_min 4.646
_cell_volume 1252.8(3)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0355
_diffrn_reflns_av_sigmaI/netI 0.0448
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 6605
_diffrn_reflns_theta_full 25.50
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_min 2.06
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.45209
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.303
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 520
_exptl_crystal_size_max 0.309
_exptl_crystal_size_mid 0.123
_exptl_crystal_size_min 0.087
_refine_diff_density_max 0.562
_refine_diff_density_min -0.332
_refine_diff_density_rms 0.059
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.047
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 328
_refine_ls_number_reflns 4580
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.047
_refine_ls_R_factor_all 0.0878
_refine_ls_R_factor_gt 0.0724
_refine_ls_shift/su_max 0.014
_refine_ls_shift/su_mean 0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1292P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1996
_refine_ls_wR_factor_ref 0.2132
_reflns_number_gt 3552
_reflns_number_total 4580
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031798_si_001.cif
_cod_data_source_block cd201540
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1252.8(4)
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1501982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.3470(2) 0.1219(2) 0.39120(14) 0.0385(5) Uani 1 1 d .
O1 O 0.4122(2) 0.2178(2) 0.25910(14) 0.0517(5) Uani 1 1 d .
O2 O 0.5208(2) -0.0666(2) 0.28674(14) 0.0605(6) Uani 1 1 d .
O3 O 0.5185(2) -0.1303(3) 0.13702(14) 0.0648(7) Uani 1 1 d .
O4 O 0.0804(2) -0.2309(2) 0.10478(15) 0.0601(6) Uani 1 1 d .
O5 O 0.2676(2) -0.2965(2) 0.21123(15) 0.0584(6) Uani 1 1 d .
O6 O -0.0003(3) 0.2105(2) 0.29141(14) 0.0645(7) Uani 1 1 d .
O7 O -0.1313(2) 0.1817(3) 0.14594(14) 0.0655(7) Uani 1 1 d .
C1 C 0.3390(3) 0.1339(3) 0.29696(17) 0.0370(6) Uani 1 1 d .
C2 C 0.2445(3) 0.0157(3) 0.41044(17) 0.0376(6) Uani 1 1 d .
C3 C 0.2185(3) -0.0260(3) 0.49726(18) 0.0476(7) Uani 1 1 d .
H3 H 0.2742 0.0153 0.5531 0.057 Uiso 1 1 calc R
C4 C 0.1070(4) -0.1313(3) 0.4983(2) 0.0587(8) Uani 1 1 d .
H4 H 0.0884 -0.1621 0.5559 0.070 Uiso 1 1 calc R
C5 C 0.0226(4) -0.1919(3) 0.4162(2) 0.0561(8) Uani 1 1 d .
H5 H -0.0534 -0.2615 0.4190 0.067 Uiso 1 1 calc R
C6 C 0.0503(3) -0.1494(3) 0.3293(2) 0.0453(7) Uani 1 1 d .
H6 H -0.0068 -0.1901 0.2737 0.054 Uiso 1 1 calc R
C7 C 0.1630(3) -0.0469(2) 0.32646(17) 0.0361(6) Uani 1 1 d .
C8 C 0.2183(3) 0.0221(2) 0.24522(16) 0.0342(6) Uani 1 1 d .
C9 C 0.1003(3) 0.0882(2) 0.17695(16) 0.0351(6) Uani 1 1 d .
C10 C 0.1276(3) 0.0820(3) 0.08991(17) 0.0396(6) Uani 1 1 d .
H10 H 0.0701 0.1207 0.0398 0.048 Uiso 1 1 calc R
C11 C 0.2606(3) 0.0062(3) 0.08040(17) 0.0409(6) Uani 1 1 d .
H11A H 0.3486 0.0674 0.0733 0.049 Uiso 1 1 calc R
H11B H 0.2368 -0.0585 0.0266 0.049 Uiso 1 1 calc R
C12 C 0.2897(3) -0.0661(2) 0.17338(16) 0.0356(6) Uani 1 1 d .
C13 C 0.4557(3) -0.0853(3) 0.20797(18) 0.0405(6) Uani 1 1 d .
C14 C 0.6741(4) -0.1674(5) 0.1591(3) 0.0793(11) Uani 1 1 d .
H14A H 0.7446 -0.0961 0.1420 0.095 Uiso 1 1 calc R
H14B H 0.7008 -0.1784 0.2264 0.095 Uiso 1 1 calc R
C15 C 0.6856(5) -0.2923(5) 0.1076(4) 0.1067(16) Uani 1 1 d .
H15A H 0.6237 -0.3645 0.1295 0.160 Uiso 1 1 calc R
H15B H 0.7899 -0.3123 0.1174 0.160 Uiso 1 1 calc R
H15C H 0.6508 -0.2833 0.0415 0.160 Uiso 1 1 calc R
C16 C 0.1990(3) -0.2061(3) 0.15739(18) 0.0414(6) Uani 1 1 d .
C17 C 0.1902(5) -0.4331(3) 0.2068(3) 0.0793(11) Uani 1 1 d .
H17A H 0.2199 -0.4743 0.2663 0.095 Uiso 1 1 calc R
H17B H 0.0808 -0.4284 0.1974 0.095 Uiso 1 1 calc R
C18 C 0.2276(7) -0.5166(4) 0.1305(4) 0.125(2) Uani 1 1 d .
H18A H 0.1758 -0.4898 0.0711 0.188 Uiso 1 1 calc R
H18B H 0.1959 -0.6099 0.1383 0.188 Uiso 1 1 calc R
H18C H 0.3357 -0.5053 0.1316 0.188 Uiso 1 1 calc R
C19 C -0.0133(3) 0.1655(3) 0.21225(18) 0.0416(6) Uani 1 1 d .
C20 C -0.2476(5) 0.2598(6) 0.1746(3) 0.0961(15) Uani 1 1 d .
H20A H -0.3041 0.2071 0.2151 0.115 Uiso 1 1 calc R
H20B H -0.1991 0.3416 0.2104 0.115 Uiso 1 1 calc R
C21 C -0.3478(6) 0.2942(6) 0.0957(3) 0.1112(18) Uani 1 1 d .
H21A H -0.2941 0.3555 0.0597 0.167 Uiso 1 1 calc R
H21B H -0.4298 0.3369 0.1160 0.167 Uiso 1 1 calc R
H21C H -0.3884 0.2139 0.0572 0.167 Uiso 1 1 calc R
C22 C 0.4505(3) 0.2079(3) 0.46239(19) 0.0468(7) Uani 1 1 d .
H22A H 0.5341 0.2480 0.4341 0.056 Uiso 1 1 calc R
H22B H 0.4932 0.1523 0.5122 0.056 Uiso 1 1 calc R
C23 C 0.3763(3) 0.3199(3) 0.50560(18) 0.0400(6) Uani 1 1 d .
C24 C 0.4278(4) 0.3652(3) 0.5973(2) 0.0616(9) Uani 1 1 d .
H24 H 0.5049 0.3242 0.6339 0.074 Uiso 1 1 calc R
C25 C 0.3653(5) 0.4722(4) 0.6358(2) 0.0798(12) Uani 1 1 d .
H25 H 0.4001 0.5021 0.6984 0.096 Uiso 1 1 calc R
C26 C 0.2534(4) 0.5338(3) 0.5828(3) 0.0671(9) Uani 1 1 d .
H26 H 0.2129 0.6064 0.6087 0.081 Uiso 1 1 calc R
C27 C 0.2017(4) 0.4894(3) 0.4928(2) 0.0588(8) Uani 1 1 d .
H27 H 0.1241 0.5306 0.4567 0.071 Uiso 1 1 calc R
C28 C 0.2630(3) 0.3830(3) 0.4534(2) 0.0504(7) Uani 1 1 d .
H28 H 0.2270 0.3537 0.3908 0.061 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0404(12) 0.0435(12) 0.0301(10) -0.0057(9) 0.0005(9) 0.0099(9)
O1 0.0571(12) 0.0511(12) 0.0452(11) 0.0006(9) 0.0096(9) -0.0032(9)
O2 0.0526(12) 0.0785(15) 0.0457(11) -0.0154(10) -0.0105(10) 0.0244(10)
O3 0.0443(12) 0.1046(18) 0.0475(12) -0.0090(11) 0.0041(9) 0.0302(11)
O4 0.0547(13) 0.0559(13) 0.0603(13) -0.0047(10) -0.0117(11) -0.0021(10)
O5 0.0638(13) 0.0422(11) 0.0660(13) 0.0082(10) -0.0018(11) 0.0096(9)
O6 0.0641(14) 0.0930(17) 0.0377(11) -0.0124(11) 0.0015(10) 0.0341(12)
O7 0.0530(12) 0.1054(18) 0.0409(11) -0.0055(11) 0.0001(9) 0.0413(12)
C1 0.0387(13) 0.0396(13) 0.0337(13) 0.0008(11) 0.0059(11) 0.0093(11)
C2 0.0398(14) 0.0428(14) 0.0328(12) 0.0033(10) 0.0054(10) 0.0191(11)
C3 0.0567(17) 0.0599(18) 0.0306(13) 0.0051(12) 0.0079(12) 0.0269(14)
C4 0.073(2) 0.0624(19) 0.0537(18) 0.0220(15) 0.0312(16) 0.0333(17)
C5 0.0585(18) 0.0495(17) 0.070(2) 0.0148(15) 0.0312(16) 0.0148(14)
C6 0.0421(15) 0.0450(15) 0.0504(16) 0.0030(12) 0.0104(12) 0.0082(11)
C7 0.0362(13) 0.0401(13) 0.0337(12) 0.0025(10) 0.0056(10) 0.0130(10)
C8 0.0360(13) 0.0390(13) 0.0277(12) -0.0014(10) 0.0034(10) 0.0096(10)
C9 0.0366(13) 0.0378(13) 0.0297(12) 0.0007(10) 0.0008(10) 0.0066(10)
C10 0.0427(14) 0.0442(14) 0.0307(12) 0.0010(11) 0.0005(11) 0.0090(11)
C11 0.0440(15) 0.0484(15) 0.0302(12) -0.0012(11) 0.0054(11) 0.0076(11)
C12 0.0358(13) 0.0401(13) 0.0304(12) -0.0037(10) 0.0028(10) 0.0091(10)
C13 0.0392(14) 0.0443(14) 0.0366(13) -0.0044(11) 0.0023(11) 0.0075(11)
C14 0.0457(19) 0.117(3) 0.076(2) -0.014(2) 0.0032(17) 0.0315(19)
C15 0.065(3) 0.094(3) 0.163(5) -0.006(3) 0.014(3) 0.034(2)
C16 0.0453(15) 0.0415(14) 0.0365(13) -0.0051(11) 0.0041(12) 0.0083(11)
C17 0.101(3) 0.0497(19) 0.086(3) 0.0133(18) 0.012(2) 0.0018(19)
C18 0.176(6) 0.048(2) 0.162(5) -0.008(3) 0.067(4) 0.006(3)
C19 0.0409(14) 0.0491(15) 0.0353(13) 0.0017(11) 0.0029(11) 0.0136(11)
C20 0.069(2) 0.168(4) 0.060(2) -0.006(2) 0.0084(19) 0.068(3)
C21 0.108(4) 0.143(4) 0.097(3) 0.020(3) 0.022(3) 0.078(3)
C22 0.0410(15) 0.0546(16) 0.0411(14) -0.0104(12) -0.0052(12) 0.0128(12)
C23 0.0419(14) 0.0398(14) 0.0365(13) -0.0031(11) 0.0039(11) 0.0022(11)
C24 0.077(2) 0.0548(18) 0.0463(16) -0.0112(14) -0.0094(16) 0.0141(16)
C25 0.115(3) 0.071(2) 0.0494(18) -0.0253(17) 0.004(2) 0.019(2)
C26 0.086(3) 0.0476(18) 0.073(2) -0.0093(16) 0.027(2) 0.0132(16)
C27 0.0616(19) 0.0497(17) 0.068(2) 0.0044(15) 0.0137(16) 0.0181(14)
C28 0.0553(17) 0.0550(17) 0.0414(15) -0.0026(13) 0.0046(13) 0.0159(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 111.4(2)
C1 N1 C22 123.9(2)
C2 N1 C22 124.7(2)
C13 O3 C14 117.6(2)
C16 O5 C17 117.5(2)
C19 O7 C20 116.2(2)
O1 C1 N1 126.4(2)
O1 C1 C8 125.5(2)
N1 C1 C8 108.1(2)
C3 C2 C7 121.6(3)
C3 C2 N1 128.2(2)
C7 C2 N1 110.2(2)
C4 C3 C2 117.6(3)
C4 C3 H3 121.2
C2 C3 H3 121.2
C5 C4 C3 121.7(3)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 120.2(3)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 119.2(3)
C7 C6 H6 120.4
C5 C6 H6 120.4
C6 C7 C2 119.7(2)
C6 C7 C8 131.9(2)
C2 C7 C8 108.4(2)
C7 C8 C9 116.9(2)
C7 C8 C1 101.96(18)
C9 C8 C1 108.86(19)
C7 C8 C12 118.02(19)
C9 C8 C12 100.57(18)
C1 C8 C12 110.5(2)
C10 C9 C19 126.5(2)
C10 C9 C8 112.1(2)
C19 C9 C8 120.8(2)
C9 C10 C11 112.6(2)
C9 C10 H10 123.7
C11 C10 H10 123.7
C10 C11 C12 103.6(2)
C10 C11 H11A 111.0
C12 C11 H11A 111.0
C10 C11 H11B 111.0
C12 C11 H11B 111.0
H11A C11 H11B 109.0
C13 C12 C16 108.2(2)
C13 C12 C11 114.3(2)
C16 C12 C11 107.67(19)
C13 C12 C8 113.23(19)
C16 C12 C8 108.8(2)
C11 C12 C8 104.39(19)
O2 C13 O3 124.1(2)
O2 C13 C12 125.8(2)
O3 C13 C12 110.0(2)
C15 C14 O3 109.4(3)
C15 C14 H14A 109.8
O3 C14 H14A 109.8
C15 C14 H14B 109.8
O3 C14 H14B 109.8
H14A C14 H14B 108.2
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O4 C16 O5 124.0(2)
O4 C16 C12 124.5(2)
O5 C16 C12 111.5(2)
C18 C17 O5 111.4(4)
C18 C17 H17A 109.3
O5 C17 H17A 109.4
C18 C17 H17B 109.4
O5 C17 H17B 109.3
H17A C17 H17B 108.0
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O6 C19 O7 123.3(2)
O6 C19 C9 124.0(2)
O7 C19 C9 112.7(2)
C21 C20 O7 110.6(3)
C21 C20 H20A 109.5
O7 C20 H20A 109.5
C21 C20 H20B 109.5
O7 C20 H20B 109.5
H20A C20 H20B 108.1
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 C23 113.8(2)
N1 C22 H22A 108.8
C23 C22 H22A 108.8
N1 C22 H22B 108.8
C23 C22 H22B 108.8
H22A C22 H22B 107.7
C24 C23 C28 118.5(3)
C24 C23 C22 119.9(2)
C28 C23 C22 121.5(2)
C23 C24 C25 120.1(3)
C23 C24 H24 120.0
C25 C24 H24 120.0
C26 C25 C24 120.5(3)
C26 C25 H25 119.7
C24 C25 H25 119.7
C27 C26 C25 119.7(3)
C27 C26 H26 120.1
C25 C26 H26 120.1
C26 C27 C28 120.4(3)
C26 C27 H27 119.8
C28 C27 H27 119.8
C23 C28 C27 120.7(3)
C23 C28 H28 119.6
C27 C28 H28 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.356(3)
N1 C2 1.398(3)
N1 C22 1.451(3)
O1 C1 1.213(3)
O2 C13 1.183(3)
O3 C13 1.328(3)
O3 C14 1.459(4)
O4 C16 1.195(3)
O5 C16 1.334(3)
O5 C17 1.458(4)
O6 C19 1.191(3)
O7 C19 1.325(3)
O7 C20 1.457(4)
C1 C8 1.549(3)
C2 C3 1.380(4)
C2 C7 1.394(3)
C3 C4 1.378(5)
C3 H3 0.9300
C4 C5 1.375(5)
C4 H4 0.9300
C5 C6 1.388(4)
C5 H5 0.9300
C6 C7 1.371(4)
C6 H6 0.9300
C7 C8 1.507(4)
C8 C9 1.529(3)
C8 C12 1.583(3)
C9 C10 1.316(4)
C9 C19 1.473(3)
C10 C11 1.488(4)
C10 H10 0.9300
C11 C12 1.537(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.516(3)
C12 C16 1.532(4)
C14 C15 1.444(6)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C17 C18 1.454(7)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C20 C21 1.398(5)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 C23 1.514(4)
C22 H22A 0.9700
C22 H22B 0.9700
C23 C24 1.367(4)
C23 C28 1.371(4)
C24 C25 1.386(5)
C24 H24 0.9300
C25 C26 1.360(5)
C25 H25 0.9300
C26 C27 1.343(5)
C26 H26 0.9300
C27 C28 1.381(4)
C27 H27 0.9300
C28 H28 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 C1 O1 178.8(2)
C22 N1 C1 O1 -2.0(4)
C2 N1 C1 C8 -0.6(3)
C22 N1 C1 C8 178.6(2)
C1 N1 C2 C3 -179.1(2)
C22 N1 C2 C3 1.7(4)
C1 N1 C2 C7 -0.3(3)
C22 N1 C2 C7 -179.5(2)
C7 C2 C3 C4 -0.9(4)
N1 C2 C3 C4 177.8(2)
C2 C3 C4 C5 -0.9(4)
C3 C4 C5 C6 1.3(4)
C4 C5 C6 C7 0.2(4)
C5 C6 C7 C2 -2.0(4)
C5 C6 C7 C8 -178.9(2)
C3 C2 C7 C6 2.4(4)
N1 C2 C7 C6 -176.6(2)
C3 C2 C7 C8 180.0(2)
N1 C2 C7 C8 1.0(3)
C6 C7 C8 C9 57.3(3)
C2 C7 C8 C9 -119.9(2)
C6 C7 C8 C1 175.9(3)
C2 C7 C8 C1 -1.3(2)
C6 C7 C8 C12 -62.9(3)
C2 C7 C8 C12 119.9(2)
O1 C1 C8 C7 -178.2(2)
N1 C1 C8 C7 1.2(2)
O1 C1 C8 C9 -54.1(3)
N1 C1 C8 C9 125.3(2)
O1 C1 C8 C12 55.5(3)
N1 C1 C8 C12 -125.1(2)
C7 C8 C9 C10 -146.9(2)
C1 C8 C9 C10 98.3(2)
C12 C8 C9 C10 -17.8(3)
C7 C8 C9 C19 41.5(3)
C1 C8 C9 C19 -73.3(3)
C12 C8 C9 C19 170.6(2)
C19 C9 C10 C11 174.1(2)
C8 C9 C10 C11 3.0(3)
C9 C10 C11 C12 13.8(3)
C10 C11 C12 C13 -148.0(2)
C10 C11 C12 C16 91.7(2)
C10 C11 C12 C8 -23.8(2)
C7 C8 C12 C13 -81.9(3)
C9 C8 C12 C13 149.7(2)
C1 C8 C12 C13 34.8(3)
C7 C8 C12 C16 38.4(3)
C9 C8 C12 C16 -90.0(2)
C1 C8 C12 C16 155.10(19)
C7 C8 C12 C11 153.1(2)
C9 C8 C12 C11 24.7(2)
C1 C8 C12 C11 -90.2(2)
C14 O3 C13 O2 4.2(5)
C14 O3 C13 C12 -174.1(3)
C16 C12 C13 O2 -103.8(3)
C11 C12 C13 O2 136.2(3)
C8 C12 C13 O2 16.8(4)
C16 C12 C13 O3 74.5(3)
C11 C12 C13 O3 -45.5(3)
C8 C12 C13 O3 -164.9(2)
C13 O3 C14 C15 137.1(4)
C17 O5 C16 O4 -1.6(4)
C17 O5 C16 C12 177.1(3)
C13 C12 C16 O4 -155.6(3)
C11 C12 C16 O4 -31.6(4)
C8 C12 C16 O4 81.0(3)
C13 C12 C16 O5 25.7(3)
C11 C12 C16 O5 149.8(2)
C8 C12 C16 O5 -97.7(2)
C16 O5 C17 C18 86.6(4)
C20 O7 C19 O6 0.3(5)
C20 O7 C19 C9 -178.7(3)
C10 C9 C19 O6 -150.9(3)
C8 C9 C19 O6 19.5(4)
C10 C9 C19 O7 28.1(4)
C8 C9 C19 O7 -161.5(2)
C19 O7 C20 C21 167.4(4)
C1 N1 C22 C23 100.3(3)
C2 N1 C22 C23 -80.6(3)
N1 C22 C23 C24 148.7(3)
N1 C22 C23 C28 -34.8(4)
C28 C23 C24 C25 0.3(5)
C22 C23 C24 C25 176.8(3)
C23 C24 C25 C26 -0.6(6)
C24 C25 C26 C27 0.9(6)
C25 C26 C27 C28 -1.0(6)
C24 C23 C28 C27 -0.3(5)
C22 C23 C28 C27 -176.8(3)
C26 C27 C28 C23 0.7(5)
|
1501983.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501983.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501983
loop_
_publ_author_name
'Zhang, Xiu-Chun'
'Cao, Shu-Hua'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
Phosphine- and nitrogen-containing Lewis base catalyzed highly
regioselective and geometric selective cyclization of isatin derived
electron-deficient alkenes with ethyl 2,3-butadienoate.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1142
_journal_page_last 1145
_journal_paper_doi 10.1021/ol1031798
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C28 H29 N O7'
_chemical_formula_weight 491.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 111.421(5)
_cell_angle_beta 93.474(6)
_cell_angle_gamma 109.002(6)
_cell_formula_units_Z 2
_cell_length_a 8.912(3)
_cell_length_b 11.563(4)
_cell_length_c 14.488(5)
_cell_measurement_reflns_used 3425
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 56.301
_cell_measurement_theta_min 4.938
_cell_volume 1286.5(8)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0229
_diffrn_reflns_av_sigmaI/netI 0.0263
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 7047
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 1.99
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.25592
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.269
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 520
_exptl_crystal_size_max 0.297
_exptl_crystal_size_mid 0.286
_exptl_crystal_size_min 0.101
_refine_diff_density_max 0.374
_refine_diff_density_min -0.275
_refine_diff_density_rms 0.051
_refine_ls_extinction_coef 0.037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 348
_refine_ls_number_reflns 4963
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.070
_refine_ls_R_factor_all 0.0718
_refine_ls_R_factor_gt 0.0616
_refine_ls_shift/su_max 0.047
_refine_ls_shift/su_mean 0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1095P)^2^+0.2040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1775
_refine_ls_wR_factor_ref 0.1883
_reflns_number_gt 3935
_reflns_number_total 4963
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031798_si_002.cif
_cod_data_source_block cd201570
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1286.4(7)
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1501983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5874(2) -0.08860(16) 0.07824(12) 0.0527(4) Uani 1 1 d . . .
O1 O 0.42116(17) -0.14193(12) 0.18756(10) 0.0547(4) Uani 1 1 d . A .
O2 O 0.21731(19) -0.06034(18) 0.45859(12) 0.0736(5) Uani 1 1 d . A .
O3 O 0.00508(18) -0.23690(17) 0.35006(12) 0.0697(5) Uani 1 1 d . A .
O4 O 0.4487(3) 0.2945(2) 0.27623(19) 0.1058(8) Uani 1 1 d . . .
O5 O 0.27803(19) 0.12982(16) 0.30556(13) 0.0716(5) Uani 1 1 d . . .
O6 O 0.8347(2) 0.2872(2) 0.39766(14) 0.0908(6) Uani 1 1 d . . .
O7 O 0.6401(3) 0.3316(2) 0.47524(15) 0.1157(10) Uani 1 1 d . . .
C1 C 0.6953(2) 0.0264(2) 0.07400(15) 0.0534(5) Uani 1 1 d . . .
C2 C 0.7855(3) 0.0389(3) 0.00124(19) 0.0702(6) Uani 1 1 d . . .
H2 H 0.7775 -0.0357 -0.0559 0.084 Uiso 1 1 calc R . .
C3 C 0.8876(3) 0.1660(3) 0.0164(2) 0.0826(8) Uani 1 1 d . . .
H3 H 0.9500 0.1774 -0.0311 0.099 Uiso 1 1 calc R . .
C4 C 0.8984(3) 0.2770(3) 0.1016(2) 0.0749(7) Uani 1 1 d . . .
H4 H 0.9680 0.3615 0.1098 0.090 Uiso 1 1 calc R . .
C5 C 0.8091(3) 0.2657(2) 0.17407(18) 0.0607(6) Uani 1 1 d . . .
H5 H 0.8179 0.3413 0.2306 0.073 Uiso 1 1 calc R . .
C6 C 0.7045(2) 0.13810(19) 0.16133(15) 0.0496(5) Uani 1 1 d . . .
C7 C 0.5991(2) 0.08685(18) 0.22021(14) 0.0456(4) Uani 1 1 d . A .
C8 C 0.5331(2) -0.04790(18) 0.16631(14) 0.0466(4) Uani 1 1 d . . .
C9 C 0.5513(2) 0.14790(18) 0.31871(14) 0.0496(5) Uani 1 1 d . . .
C10 C 0.4900(2) 0.03665(19) 0.35879(14) 0.0503(5) Uani 1 1 d . A .
H10A H 0.5825 0.0232 0.3853 0.060 Uiso 1 1 calc R . .
H10B H 0.4367 0.0667 0.4142 0.060 Uiso 1 1 calc R . .
C11 C 0.3745(2) -0.09436(18) 0.27956(14) 0.0463(4) Uani 1 1 d . . .
C12 C 0.2338(2) -0.17472(19) 0.28592(15) 0.0511(5) Uani 1 1 d . A .
H12 H 0.1789 -0.2547 0.2297 0.061 Uiso 1 1 calc R . .
C13 C 0.1578(2) -0.1476(2) 0.37463(16) 0.0540(5) Uani 1 1 d . . .
C14 C -0.0892(3) -0.2225(3) 0.4294(2) 0.0870(8) Uani 1 1 d . . .
H14A H -0.0398 -0.2353 0.4845 0.104 Uiso 1 1 calc R A .
H14B H -0.0919 -0.1332 0.4559 0.104 Uiso 1 1 calc R . .
C15 C -0.2528(5) -0.3217(6) 0.3870(3) 0.165(2) Uani 1 1 d . A .
H15A H -0.3062 -0.3009 0.3391 0.248 Uiso 1 1 calc R . .
H15B H -0.3118 -0.3210 0.4403 0.248 Uiso 1 1 calc R . .
H15C H -0.2485 -0.4088 0.3534 0.248 Uiso 1 1 calc R . .
C16 C 0.4218(3) 0.20148(19) 0.29891(15) 0.0562(5) Uani 1 1 d . A .
C17 C 0.1375(3) 0.1600(3) 0.2818(2) 0.0782(7) Uani 1 1 d . . .
H17A H 0.1380 0.1741 0.2198 0.094 Uiso 1 1 calc R . .
H17B H 0.1386 0.2402 0.3362 0.094 Uiso 1 1 calc R . .
C18 C -0.0071(3) 0.0432(3) 0.2697(3) 0.0991(10) Uani 1 1 d . . .
H18A H -0.0109 -0.0339 0.2124 0.149 Uiso 1 1 calc R . .
H18B H -0.1029 0.0615 0.2593 0.149 Uiso 1 1 calc R . .
H18C H -0.0014 0.0261 0.3296 0.149 Uiso 1 1 calc R . .
C19 C 0.6947(3) 0.2636(2) 0.39991(16) 0.0688(6) Uani 1 1 d . A .
C20 C 0.7901(7) 0.4261(5) 0.5643(5) 0.0671(13) Uani 0.50 1 d P A 1
H20A H 0.8604 0.3797 0.5712 0.080 Uiso 0.50 1 calc PR A 1
H20B H 0.8522 0.5049 0.5540 0.080 Uiso 0.50 1 calc PR A 1
C21 C 0.7172(13) 0.4621(11) 0.6530(8) 0.079(2) Uani 0.60 1 d P A 1
H21A H 0.6348 0.4938 0.6398 0.119 Uiso 0.60 1 calc PR A 1
H21B H 0.7992 0.5313 0.7102 0.119 Uiso 0.60 1 calc PR A 1
H21C H 0.6698 0.3848 0.6674 0.119 Uiso 0.60 1 calc PR A 1
C20' C 0.7250(8) 0.4724(5) 0.5494(4) 0.0817(15) Uani 0.50 1 d P A 2
H20C H 0.8169 0.5201 0.5275 0.098 Uiso 0.50 1 calc PR A 2
H20D H 0.6527 0.5209 0.5638 0.098 Uiso 0.50 1 calc PR A 2
C21' C 0.774(2) 0.447(2) 0.6337(15) 0.111(5) Uani 0.40 1 d P A 2
H21D H 0.6813 0.3896 0.6474 0.167 Uiso 0.40 1 calc PR A 2
H21E H 0.8242 0.5298 0.6923 0.167 Uiso 0.40 1 calc PR A 2
H21F H 0.8507 0.4034 0.6179 0.167 Uiso 0.40 1 calc PR A 2
C22 C 0.5290(2) -0.2237(2) -0.00138(15) 0.0554(5) Uani 1 1 d . . .
H22A H 0.5271 -0.2174 -0.0664 0.067 Uiso 1 1 calc R . .
H22B H 0.4183 -0.2706 0.0013 0.067 Uiso 1 1 calc R . .
C23 C 0.6273(2) -0.30619(19) 0.00404(14) 0.0491(4) Uani 1 1 d . . .
C24 C 0.7096(3) -0.2914(2) 0.09429(17) 0.0644(6) Uani 1 1 d . . .
H24 H 0.7113 -0.2243 0.1548 0.077 Uiso 1 1 calc R . .
C25 C 0.7897(3) -0.3761(3) 0.0951(2) 0.0783(7) Uani 1 1 d . . .
H25 H 0.8453 -0.3648 0.1561 0.094 Uiso 1 1 calc R . .
C26 C 0.7872(3) -0.4760(3) 0.0067(3) 0.0781(7) Uani 1 1 d . . .
H26 H 0.8407 -0.5327 0.0075 0.094 Uiso 1 1 calc R . .
C27 C 0.7052(3) -0.4917(2) -0.0827(2) 0.0768(7) Uani 1 1 d . . .
H27 H 0.7022 -0.5599 -0.1429 0.092 Uiso 1 1 calc R . .
C28 C 0.6271(3) -0.4072(2) -0.08415(17) 0.0624(5) Uani 1 1 d . . .
H28 H 0.5732 -0.4183 -0.1457 0.075 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0538(10) 0.0502(9) 0.0546(9) 0.0199(7) 0.0180(7) 0.0203(7)
O1 0.0577(8) 0.0414(7) 0.0598(8) 0.0182(6) 0.0202(6) 0.0133(6)
O2 0.0672(10) 0.0847(12) 0.0560(9) 0.0256(9) 0.0138(7) 0.0158(9)
O3 0.0544(9) 0.0770(10) 0.0692(10) 0.0301(8) 0.0220(7) 0.0121(8)
O4 0.1269(17) 0.0939(14) 0.166(2) 0.0927(15) 0.0786(16) 0.0723(14)
O5 0.0577(9) 0.0619(9) 0.1049(13) 0.0423(9) 0.0058(8) 0.0265(8)
O6 0.0631(11) 0.0895(13) 0.0814(12) 0.0222(10) -0.0092(9) 0.0001(9)
O7 0.1090(17) 0.0771(14) 0.0619(12) -0.0232(10) 0.0332(12) -0.0293(12)
C1 0.0459(11) 0.0611(12) 0.0584(11) 0.0302(10) 0.0114(8) 0.0196(9)
C2 0.0647(14) 0.0879(17) 0.0690(14) 0.0407(13) 0.0266(11) 0.0296(13)
C3 0.0644(15) 0.111(2) 0.0934(19) 0.0672(18) 0.0329(13) 0.0268(15)
C4 0.0554(13) 0.0829(17) 0.0955(19) 0.0578(16) 0.0155(12) 0.0125(12)
C5 0.0508(12) 0.0590(12) 0.0748(14) 0.0376(11) 0.0061(10) 0.0131(9)
C6 0.0410(10) 0.0526(11) 0.0591(11) 0.0288(9) 0.0061(8) 0.0159(8)
C7 0.0433(10) 0.0436(9) 0.0496(10) 0.0199(8) 0.0089(7) 0.0151(8)
C8 0.0441(10) 0.0459(10) 0.0520(10) 0.0219(8) 0.0129(8) 0.0167(8)
C9 0.0521(11) 0.0413(9) 0.0488(10) 0.0167(8) 0.0073(8) 0.0116(8)
C10 0.0474(10) 0.0529(11) 0.0509(10) 0.0241(9) 0.0068(8) 0.0163(8)
C11 0.0500(10) 0.0461(10) 0.0513(10) 0.0252(8) 0.0124(8) 0.0219(8)
C12 0.0524(11) 0.0442(10) 0.0582(11) 0.0224(9) 0.0123(8) 0.0181(8)
C13 0.0503(11) 0.0585(12) 0.0607(12) 0.0316(10) 0.0127(9) 0.0208(9)
C14 0.0683(16) 0.108(2) 0.0833(17) 0.0428(16) 0.0344(13) 0.0230(15)
C15 0.081(2) 0.220(5) 0.122(3) 0.046(3) 0.046(2) -0.010(3)
C16 0.0752(14) 0.0437(10) 0.0547(11) 0.0193(9) 0.0207(10) 0.0279(10)
C17 0.0828(18) 0.0754(16) 0.0906(17) 0.0323(14) 0.0085(13) 0.0504(14)
C18 0.0635(17) 0.095(2) 0.129(3) 0.0299(19) -0.0099(16) 0.0408(16)
C19 0.0764(17) 0.0528(12) 0.0510(12) 0.0160(10) 0.0064(11) -0.0010(11)
C20 0.069(3) 0.052(3) 0.055(3) 0.001(2) -0.004(3) 0.018(2)
C21 0.096(6) 0.061(3) 0.059(3) 0.009(2) 0.005(3) 0.022(4)
C20' 0.094(4) 0.052(3) 0.071(3) 0.006(2) -0.003(3) 0.018(3)
C21' 0.117(14) 0.098(11) 0.089(12) 0.029(10) -0.002(9) 0.020(8)
C22 0.0523(11) 0.0550(11) 0.0519(11) 0.0150(9) 0.0071(8) 0.0198(9)
C23 0.0418(10) 0.0472(10) 0.0517(10) 0.0194(8) 0.0104(8) 0.0094(8)
C24 0.0570(13) 0.0692(14) 0.0610(13) 0.0257(11) 0.0055(10) 0.0184(11)
C25 0.0531(13) 0.0964(19) 0.0970(19) 0.0586(17) 0.0066(12) 0.0220(13)
C26 0.0592(14) 0.0734(16) 0.128(2) 0.0614(17) 0.0337(15) 0.0310(12)
C27 0.0869(18) 0.0558(13) 0.0951(18) 0.0303(13) 0.0331(15) 0.0337(13)
C28 0.0703(14) 0.0559(12) 0.0590(12) 0.0208(10) 0.0143(10) 0.0239(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 106.56(16)
C8 N1 C22 126.66(17)
C1 N1 C22 126.40(17)
C8 O1 C11 115.53(14)
C13 O3 C14 116.91(19)
C16 O5 C17 119.92(18)
C19 O7 C20' 126.9(3)
C19 O7 C20 106.7(3)
C20' O7 C20 37.0(3)
C2 C1 N1 129.3(2)
C2 C1 C6 122.4(2)
N1 C1 C6 108.37(17)
C3 C2 C1 117.7(2)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 120.9(2)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 121.9(2)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 118.8(2)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 118.40(19)
C5 C6 C7 134.8(2)
C1 C6 C7 106.79(17)
C8 C7 C6 105.51(16)
C8 C7 C9 119.45(16)
C6 C7 C9 135.03(17)
O1 C8 C7 128.74(17)
O1 C8 N1 118.46(16)
C7 C8 N1 112.77(17)
C7 C9 C16 108.08(15)
C7 C9 C19 112.72(17)
C16 C9 C19 108.82(18)
C7 C9 C10 107.05(15)
C16 C9 C10 113.23(16)
C19 C9 C10 107.04(16)
C11 C10 C9 113.39(15)
C11 C10 H10A 108.9
C9 C10 H10A 108.9
C11 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.7
C12 C11 O1 114.63(17)
C12 C11 C10 128.67(18)
O1 C11 C10 116.66(16)
C11 C12 C13 125.28(19)
C11 C12 H12 117.4
C13 C12 H12 117.4
O2 C13 O3 122.46(19)
O2 C13 C12 127.73(19)
O3 C13 C12 109.81(18)
C15 C14 O3 108.8(3)
C15 C14 H14A 109.9
O3 C14 H14A 109.9
C15 C14 H14B 109.9
O3 C14 H14B 109.9
H14A C14 H14B 108.3
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O4 C16 O5 124.3(2)
O4 C16 C9 123.4(2)
O5 C16 C9 112.22(16)
O5 C17 C18 106.5(2)
O5 C17 H17A 110.4
C18 C17 H17A 110.4
O5 C17 H17B 110.4
C18 C17 H17B 110.4
H17A C17 H17B 108.6
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O6 C19 O7 124.4(2)
O6 C19 C9 126.0(2)
O7 C19 C9 109.6(2)
C21 C20 O7 103.5(6)
C21 C20 H20A 111.0
O7 C20 H20A 111.1
C21 C20 H20B 111.1
O7 C20 H20B 111.1
H20A C20 H20B 109.0
C21' C20' O7 98.3(10)
C21' C20' H20C 112.1
O7 C20' H20C 112.1
C21' C20' H20D 112.1
O7 C20' H20D 112.1
H20C C20' H20D 109.7
C20' C21' H21D 109.5
C20' C21' H21E 109.4
H21D C21' H21E 109.5
C20' C21' H21F 109.5
H21D C21' H21F 109.5
H21E C21' H21F 109.5
N1 C22 C23 115.17(16)
N1 C22 H22A 108.5
C23 C22 H22A 108.5
N1 C22 H22B 108.5
C23 C22 H22B 108.5
H22A C22 H22B 107.5
C28 C23 C24 118.1(2)
C28 C23 C22 118.75(18)
C24 C23 C22 123.06(19)
C23 C24 C25 120.5(2)
C23 C24 H24 119.8
C25 C24 H24 119.8
C26 C25 C24 120.4(2)
C26 C25 H25 119.8
C24 C25 H25 119.8
C27 C26 C25 119.4(2)
C27 C26 H26 120.3
C25 C26 H26 120.3
C26 C27 C28 120.5(2)
C26 C27 H27 119.8
C28 C27 H27 119.8
C27 C28 C23 121.2(2)
C27 C28 H28 119.4
C23 C28 H28 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.367(2)
N1 C1 1.389(3)
N1 C22 1.457(3)
O1 C8 1.359(2)
O1 C11 1.390(2)
O2 C13 1.206(3)
O3 C13 1.343(3)
O3 C14 1.457(3)
O4 C16 1.192(3)
O5 C16 1.311(3)
O5 C17 1.458(3)
O6 C19 1.192(3)
O7 C19 1.317(3)
O7 C20' 1.482(5)
O7 C20 1.567(6)
C1 C2 1.384(3)
C1 C6 1.415(3)
C2 C3 1.380(4)
C2 H2 0.9300
C3 C4 1.389(4)
C3 H3 0.9300
C4 C5 1.374(3)
C4 H4 0.9300
C5 C6 1.402(3)
C5 H5 0.9300
C6 C7 1.437(3)
C7 C8 1.357(3)
C7 C9 1.500(3)
C9 C16 1.535(3)
C9 C19 1.537(3)
C9 C10 1.555(3)
C10 C11 1.498(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.328(3)
C12 C13 1.469(3)
C12 H12 0.9300
C14 C15 1.451(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C17 C18 1.477(4)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C20 C21 1.460(10)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C20' C21' 1.44(2)
C20' H20C 0.9700
C20' H20D 0.9700
C21' H21D 0.9600
C21' H21E 0.9600
C21' H21F 0.9600
C22 C23 1.508(3)
C22 H22A 0.9700
C22 H22B 0.9700
C23 C28 1.380(3)
C23 C24 1.384(3)
C24 C25 1.390(4)
C24 H24 0.9300
C25 C26 1.369(4)
C25 H25 0.9300
C26 C27 1.369(4)
C26 H26 0.9300
C27 C28 1.376(3)
C27 H27 0.9300
C28 H28 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N1 C1 C2 178.6(2)
C22 N1 C1 C2 -8.1(3)
C8 N1 C1 C6 -0.4(2)
C22 N1 C1 C6 172.86(17)
N1 C1 C2 C3 -178.6(2)
C6 C1 C2 C3 0.3(3)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 177.6(2)
C2 C1 C6 C5 -0.1(3)
N1 C1 C6 C5 178.98(16)
C2 C1 C6 C7 -178.36(19)
N1 C1 C6 C7 0.7(2)
C5 C6 C7 C8 -178.6(2)
C1 C6 C7 C8 -0.7(2)
C5 C6 C7 C9 2.5(4)
C1 C6 C7 C9 -179.7(2)
C11 O1 C8 C7 -3.9(3)
C11 O1 C8 N1 178.28(15)
C6 C7 C8 O1 -177.47(18)
C9 C7 C8 O1 1.7(3)
C6 C7 C8 N1 0.5(2)
C9 C7 C8 N1 179.65(16)
C1 N1 C8 O1 178.14(16)
C22 N1 C8 O1 4.9(3)
C1 N1 C8 C7 -0.1(2)
C22 N1 C8 C7 -173.32(18)
C8 C7 C9 C16 -98.8(2)
C6 C7 C9 C16 80.0(2)
C8 C7 C9 C19 140.90(19)
C6 C7 C9 C19 -40.3(3)
C8 C7 C9 C10 23.5(2)
C6 C7 C9 C10 -157.7(2)
C7 C9 C10 C11 -46.4(2)
C16 C9 C10 C11 72.6(2)
C19 C9 C10 C11 -167.49(18)
C8 O1 C11 C12 159.90(16)
C8 O1 C11 C10 -22.0(2)
C9 C10 C11 C12 -133.6(2)
C9 C10 C11 O1 48.7(2)
O1 C11 C12 C13 -179.91(16)
C10 C11 C12 C13 2.3(3)
C14 O3 C13 O2 1.4(3)
C14 O3 C13 C12 -178.8(2)
C11 C12 C13 O2 -10.8(3)
C11 C12 C13 O3 169.42(18)
C13 O3 C14 C15 176.3(3)
C17 O5 C16 O4 1.7(3)
C17 O5 C16 C9 -175.55(19)
C7 C9 C16 O4 -68.1(3)
C19 C9 C16 O4 54.6(3)
C10 C9 C16 O4 173.5(2)
C7 C9 C16 O5 109.12(19)
C19 C9 C16 O5 -128.17(19)
C10 C9 C16 O5 -9.3(2)
C16 O5 C17 C18 165.2(2)
C20' O7 C19 O6 24.8(6)
C20 O7 C19 O6 -10.2(5)
C20' O7 C19 C9 -157.2(4)
C20 O7 C19 C9 167.8(3)
C7 C9 C19 O6 -16.2(3)
C16 C9 C19 O6 -136.1(3)
C10 C9 C19 O6 101.2(3)
C7 C9 C19 O7 165.9(2)
C16 C9 C19 O7 46.0(3)
C10 C9 C19 O7 -76.7(3)
C19 O7 C20 C21 -161.2(6)
C20' O7 C20 C21 68.6(7)
C19 O7 C20' C21' -103.0(8)
C20 O7 C20' C21' -36.7(7)
C8 N1 C22 C23 -96.4(2)
C1 N1 C22 C23 91.6(2)
N1 C22 C23 C28 -153.45(18)
N1 C22 C23 C24 30.9(3)
C28 C23 C24 C25 0.2(3)
C22 C23 C24 C25 175.9(2)
C23 C24 C25 C26 -0.5(4)
C24 C25 C26 C27 0.1(4)
C25 C26 C27 C28 0.6(4)
C26 C27 C28 C23 -0.9(4)
C24 C23 C28 C27 0.5(3)
C22 C23 C28 C27 -175.3(2)
|
1501984.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501984.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501984
loop_
_publ_author_name
'Zhang, Xiu-Chun'
'Cao, Shu-Hua'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
Phosphine- and nitrogen-containing Lewis base catalyzed highly
regioselective and geometric selective cyclization of isatin derived
electron-deficient alkenes with ethyl 2,3-butadienoate.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1142
_journal_page_last 1145
_journal_paper_doi 10.1021/ol1031798
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C28 H29 N O7'
_chemical_formula_weight 491.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 103.573(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.6480(13)
_cell_length_b 18.681(2)
_cell_length_c 11.3502(12)
_cell_measurement_reflns_used 1747
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 47.421
_cell_measurement_theta_min 4.860
_cell_volume 2606.9(5)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0987
_diffrn_reflns_av_sigmaI/netI 0.0812
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 13561
_diffrn_reflns_theta_full 25.50
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_min 2.14
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.58724
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.252
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 1040
_exptl_crystal_size_max 0.213
_exptl_crystal_size_mid 0.203
_exptl_crystal_size_min 0.127
_refine_diff_density_max 0.543
_refine_diff_density_min -0.313
_refine_diff_density_rms 0.064
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.881
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 329
_refine_ls_number_reflns 4845
_refine_ls_number_restraints 6
_refine_ls_restrained_S_all 0.900
_refine_ls_R_factor_all 0.1199
_refine_ls_R_factor_gt 0.0726
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1741
_refine_ls_wR_factor_ref 0.1967
_reflns_number_gt 2446
_reflns_number_total 4845
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031798_si_003.cif
_cod_data_source_block cd201574
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2607.0(5)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1501984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.3743(2) -0.02489(13) 0.5246(2) 0.0446(7) Uani 1 1 d .
O1 O 0.29304(17) 0.08580(10) 0.54195(18) 0.0437(6) Uani 1 1 d .
O2 O 0.1260(2) 0.18852(16) 0.7316(3) 0.0862(9) Uani 1 1 d .
O3 O 0.06148(18) 0.12061(12) 0.5699(2) 0.0579(7) Uani 1 1 d .
O4 O 0.3858(2) 0.17780(13) 0.2364(2) 0.0606(7) Uani 1 1 d .
O5 O 0.3243(2) 0.09234(15) 0.1020(2) 0.0767(9) Uani 1 1 d .
O6 O 0.1085(2) 0.01163(13) 0.1768(2) 0.0683(8) Uani 1 1 d .
O7 O 0.09971(19) 0.12498(12) 0.1121(2) 0.0602(7) Uani 1 1 d .
C1 C 0.3922(3) -0.06820(16) 0.4333(3) 0.0449(8) Uani 1 1 d .
C2 C 0.4436(3) -0.13479(18) 0.4410(4) 0.0597(10) Uani 1 1 d .
H2 H 0.4726 -0.1564 0.5154 0.072 Uiso 1 1 calc R
C3 C 0.4495(3) -0.16707(19) 0.3334(5) 0.0710(12) Uani 1 1 d .
H3 H 0.4854 -0.2107 0.3359 0.085 Uiso 1 1 calc R
C4 C 0.4040(3) -0.1367(2) 0.2223(4) 0.0720(12) Uani 1 1 d .
H4 H 0.4069 -0.1614 0.1519 0.086 Uiso 1 1 calc R
C5 C 0.3537(3) -0.06980(18) 0.2133(3) 0.0589(10) Uani 1 1 d .
H5 H 0.3249 -0.0492 0.1380 0.071 Uiso 1 1 calc R
C6 C 0.3478(3) -0.03454(16) 0.3201(3) 0.0441(8) Uani 1 1 d .
C7 C 0.3036(2) 0.03291(15) 0.3478(3) 0.0390(8) Uani 1 1 d .
C8 C 0.3218(2) 0.03496(15) 0.4717(3) 0.0395(8) Uani 1 1 d .
C9 C 0.2491(2) 0.09535(16) 0.2735(3) 0.0409(8) Uani 1 1 d .
C10 C 0.2193(2) 0.15032(15) 0.3576(3) 0.0426(8) Uani 1 1 d .
H10 H 0.1846 0.1917 0.3228 0.051 Uiso 1 1 calc R
C11 C 0.2387(2) 0.14431(15) 0.4771(3) 0.0411(8) Uani 1 1 d .
C12 C 0.2096(3) 0.19651(17) 0.5640(3) 0.0477(8) Uani 1 1 d .
H12A H 0.1793 0.2390 0.5195 0.057 Uiso 1 1 calc R
H12B H 0.2755 0.2107 0.6219 0.057 Uiso 1 1 calc R
C13 C 0.1300(3) 0.16900(17) 0.6322(3) 0.0518(9) Uani 1 1 d .
C14 C -0.0213(3) 0.09138(19) 0.6270(4) 0.0619(10) Uani 1 1 d .
H14A H 0.0106 0.0830 0.7122 0.074 Uiso 1 1 calc R
H14B H -0.0462 0.0458 0.5899 0.074 Uiso 1 1 calc R
C15 C -0.1155(3) 0.1404(2) 0.6147(4) 0.0724(12) Uani 1 1 d .
H15A H -0.0915 0.1851 0.6537 0.109 Uiso 1 1 calc R
H15B H -0.1686 0.1192 0.6521 0.109 Uiso 1 1 calc R
H15C H -0.1474 0.1486 0.5304 0.109 Uiso 1 1 calc R
C16 C 0.3273(3) 0.12802(18) 0.2032(3) 0.0457(8) Uani 1 1 d .
C17 C 0.3931(4) 0.1173(3) 0.0241(4) 0.1056(18) Uani 1 1 d .
H17A H 0.3927 0.1692 0.0212 0.127 Uiso 1 1 calc R
H17B H 0.4673 0.1014 0.0560 0.127 Uiso 1 1 calc R
C18 C 0.3553(6) 0.0908(5) -0.0869(6) 0.189(3) Uani 1 1 d U
H18A H 0.3826 0.0432 -0.0907 0.284 Uiso 1 1 calc R
H18B H 0.3789 0.1206 -0.1448 0.284 Uiso 1 1 calc R
H18C H 0.2773 0.0898 -0.1050 0.284 Uiso 1 1 calc R
C19 C 0.1456(3) 0.07096(18) 0.1812(3) 0.0482(8) Uani 1 1 d .
C20 C 0.0050(3) 0.1061(2) 0.0147(3) 0.0738(12) Uani 1 1 d .
H20A H 0.0272 0.0752 -0.0439 0.089 Uiso 1 1 calc R
H20B H -0.0483 0.0808 0.0479 0.089 Uiso 1 1 calc R
C21 C -0.0423(4) 0.1724(2) -0.0443(4) 0.0849(14) Uani 1 1 d .
H21A H -0.0644 0.2025 0.0141 0.127 Uiso 1 1 calc R
H21B H -0.1043 0.1611 -0.1084 0.127 Uiso 1 1 calc R
H21C H 0.0109 0.1970 -0.0773 0.127 Uiso 1 1 calc R
C22 C 0.3970(3) -0.04111(18) 0.6546(3) 0.0507(9) Uani 1 1 d .
H22A H 0.4078 0.0033 0.7000 0.061 Uiso 1 1 calc R
H22B H 0.4638 -0.0686 0.6772 0.061 Uiso 1 1 calc R
C23 C 0.3062(3) -0.08281(17) 0.6882(3) 0.0489(9) Uani 1 1 d .
C24 C 0.3190(3) -0.15459(19) 0.7190(4) 0.0661(11) Uani 1 1 d .
H24 H 0.3851 -0.1770 0.7215 0.079 Uiso 1 1 calc R
C25 C 0.2347(4) -0.1931(2) 0.7458(4) 0.0796(13) Uani 1 1 d .
H25 H 0.2452 -0.2410 0.7674 0.095 Uiso 1 1 calc R
C26 C 0.1360(4) -0.1622(2) 0.7413(4) 0.0755(12) Uani 1 1 d .
H26 H 0.0796 -0.1889 0.7592 0.091 Uiso 1 1 calc R
C27 C 0.1210(3) -0.0910(2) 0.7100(4) 0.0745(12) Uani 1 1 d .
H27 H 0.0542 -0.0693 0.7061 0.089 Uiso 1 1 calc R
C28 C 0.2060(3) -0.0521(2) 0.6845(3) 0.0620(10) Uani 1 1 d .
H28 H 0.1955 -0.0039 0.6643 0.074 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0516(17) 0.0331(14) 0.0461(16) 0.0086(12) 0.0051(13) 0.0020(12)
O1 0.0597(14) 0.0340(12) 0.0346(12) 0.0032(9) 0.0053(10) 0.0013(10)
O2 0.119(2) 0.089(2) 0.0575(18) -0.0320(16) 0.0340(16) -0.0355(18)
O3 0.0638(16) 0.0547(14) 0.0565(15) -0.0167(12) 0.0170(13) -0.0115(12)
O4 0.0663(16) 0.0515(15) 0.0610(16) 0.0057(12) 0.0087(13) -0.0165(13)
O5 0.110(2) 0.0823(19) 0.0480(16) -0.0134(14) 0.0384(15) -0.0332(16)
O6 0.0765(18) 0.0453(15) 0.0700(18) 0.0030(12) -0.0091(14) -0.0193(13)
O7 0.0721(16) 0.0473(14) 0.0450(14) 0.0032(11) -0.0186(12) -0.0060(12)
C1 0.047(2) 0.0289(16) 0.059(2) -0.0001(15) 0.0121(16) -0.0049(14)
C2 0.055(2) 0.0359(19) 0.088(3) 0.006(2) 0.017(2) 0.0006(16)
C3 0.072(3) 0.038(2) 0.104(4) -0.011(2) 0.021(3) -0.0008(19)
C4 0.082(3) 0.052(2) 0.088(3) -0.029(2) 0.031(3) -0.011(2)
C5 0.075(3) 0.047(2) 0.057(2) -0.0118(18) 0.019(2) -0.0081(18)
C6 0.048(2) 0.0343(17) 0.051(2) -0.0034(15) 0.0134(16) -0.0054(14)
C7 0.051(2) 0.0275(15) 0.0386(18) 0.0023(13) 0.0117(15) -0.0015(13)
C8 0.0479(19) 0.0278(16) 0.0415(18) 0.0034(14) 0.0075(15) -0.0028(13)
C9 0.0487(19) 0.0329(16) 0.0383(18) 0.0010(14) 0.0045(15) -0.0027(14)
C10 0.052(2) 0.0293(16) 0.0431(19) 0.0036(14) 0.0042(15) 0.0009(14)
C11 0.0479(19) 0.0304(16) 0.0417(19) 0.0009(14) 0.0040(15) -0.0012(14)
C12 0.058(2) 0.0323(17) 0.050(2) -0.0078(15) 0.0076(17) -0.0029(15)
C13 0.067(2) 0.0396(19) 0.048(2) -0.0132(17) 0.0115(18) 0.0006(17)
C14 0.070(3) 0.053(2) 0.065(2) -0.0006(19) 0.020(2) -0.0065(19)
C15 0.070(3) 0.074(3) 0.073(3) -0.004(2) 0.018(2) -0.006(2)
C16 0.055(2) 0.0400(18) 0.0376(19) 0.0101(15) 0.0027(15) -0.0001(16)
C17 0.123(4) 0.143(5) 0.064(3) -0.019(3) 0.048(3) -0.045(4)
C18 0.194(6) 0.284(8) 0.107(5) -0.027(5) 0.071(5) -0.066(6)
C19 0.063(2) 0.0414(19) 0.0363(19) 0.0011(15) 0.0043(16) -0.0033(17)
C20 0.084(3) 0.065(3) 0.054(2) -0.009(2) -0.020(2) -0.006(2)
C21 0.104(3) 0.078(3) 0.054(2) 0.006(2) -0.018(2) 0.008(3)
C22 0.054(2) 0.0424(18) 0.048(2) 0.0110(16) -0.0040(16) 0.0006(16)
C23 0.060(2) 0.045(2) 0.0377(18) 0.0119(15) 0.0035(16) -0.0011(17)
C24 0.066(2) 0.051(2) 0.081(3) 0.025(2) 0.018(2) 0.0063(19)
C25 0.084(3) 0.053(2) 0.103(4) 0.029(2) 0.026(3) -0.001(2)
C26 0.081(3) 0.064(3) 0.088(3) 0.017(2) 0.034(2) -0.006(2)
C27 0.080(3) 0.063(3) 0.090(3) 0.024(2) 0.038(2) 0.014(2)
C28 0.077(3) 0.046(2) 0.066(3) 0.0172(19) 0.024(2) 0.009(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 107.4(3)
C8 N1 C22 124.9(3)
C1 N1 C22 127.5(3)
C8 O1 C11 114.0(2)
C13 O3 C14 117.6(3)
C16 O5 C17 117.9(3)
C19 O7 C20 115.4(3)
N1 C1 C2 129.3(3)
N1 C1 C6 108.7(3)
C2 C1 C6 122.0(3)
C3 C2 C1 117.1(4)
C3 C2 H2 121.5
C1 C2 H2 121.5
C4 C3 C2 122.1(4)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 121.4(4)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C6 118.4(4)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 119.0(3)
C5 C6 C7 134.7(3)
C1 C6 C7 106.2(3)
C8 C7 C6 105.6(3)
C8 C7 C9 119.8(3)
C6 C7 C9 134.7(3)
O1 C8 N1 119.3(3)
O1 C8 C7 128.7(3)
N1 C8 C7 112.1(3)
C10 C9 C7 108.8(2)
C10 C9 C16 110.2(2)
C7 C9 C16 109.4(3)
C10 C9 C19 109.5(3)
C7 C9 C19 110.8(2)
C16 C9 C19 108.2(3)
C11 C10 C9 125.2(3)
C11 C10 H10 117.4
C9 C10 H10 117.4
C10 C11 O1 123.6(3)
C10 C11 C12 127.3(3)
O1 C11 C12 109.2(3)
C11 C12 C13 114.7(3)
C11 C12 H12A 108.6
C13 C12 H12A 108.6
C11 C12 H12B 108.6
C13 C12 H12B 108.6
H12A C12 H12B 107.6
O2 C13 O3 122.6(3)
O2 C13 C12 124.4(3)
O3 C13 C12 113.0(3)
O3 C14 C15 111.8(3)
O3 C14 H14A 109.3
C15 C14 H14A 109.3
O3 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 107.9
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O4 C16 O5 123.9(3)
O4 C16 C9 125.0(3)
O5 C16 C9 111.1(3)
C18 C17 O5 108.8(5)
C18 C17 H17A 109.9
O5 C17 H17A 109.9
C18 C17 H17B 109.9
O5 C17 H17B 109.9
H17A C17 H17B 108.3
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O6 C19 O7 124.4(3)
O6 C19 C9 124.3(3)
O7 C19 C9 111.2(3)
C21 C20 O7 108.3(3)
C21 C20 H20A 110.0
O7 C20 H20A 110.0
C21 C20 H20B 110.0
O7 C20 H20B 110.0
H20A C20 H20B 108.4
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 C23 112.3(3)
N1 C22 H22A 109.1
C23 C22 H22A 109.1
N1 C22 H22B 109.1
C23 C22 H22B 109.1
H22A C22 H22B 107.9
C28 C23 C24 117.5(3)
C28 C23 C22 121.6(3)
C24 C23 C22 120.9(3)
C25 C24 C23 120.7(4)
C25 C24 H24 119.7
C23 C24 H24 119.7
C26 C25 C24 121.3(4)
C26 C25 H25 119.3
C24 C25 H25 119.3
C25 C26 C27 119.1(4)
C25 C26 H26 120.5
C27 C26 H26 120.5
C26 C27 C28 119.7(4)
C26 C27 H27 120.2
C28 C27 H27 120.2
C23 C28 C27 121.8(3)
C23 C28 H28 119.1
C27 C28 H28 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.366(4)
N1 C1 1.375(4)
N1 C22 1.467(4)
O1 C8 1.344(3)
O1 C11 1.404(3)
O2 C13 1.198(4)
O3 C13 1.334(4)
O3 C14 1.460(4)
O4 C16 1.193(4)
O5 C16 1.321(4)
O5 C17 1.455(5)
O6 C19 1.200(4)
O7 C19 1.326(4)
O7 C20 1.469(4)
C1 C2 1.397(4)
C1 C6 1.423(4)
C2 C3 1.380(5)
C2 H2 0.9300
C3 C4 1.379(6)
C3 H3 0.9300
C4 C5 1.396(5)
C4 H4 0.9300
C5 C6 1.397(4)
C5 H5 0.9300
C6 C7 1.443(4)
C7 C8 1.371(4)
C7 C9 1.508(4)
C9 C10 1.508(4)
C9 C16 1.536(4)
C9 C19 1.541(4)
C10 C11 1.325(4)
C10 H10 0.9300
C11 C12 1.494(4)
C12 C13 1.497(5)
C12 H12A 0.9700
C12 H12B 0.9700
C14 C15 1.483(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C17 C18 1.332(7)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C20 C21 1.466(5)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 C23 1.509(4)
C22 H22A 0.9700
C22 H22B 0.9700
C23 C28 1.383(5)
C23 C24 1.385(4)
C24 C25 1.378(5)
C24 H24 0.9300
C25 C26 1.364(5)
C25 H25 0.9300
C26 C27 1.379(5)
C26 H26 0.9300
C27 C28 1.384(5)
C27 H27 0.9300
C28 H28 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N1 C1 C2 179.4(3)
C22 N1 C1 C2 -5.9(5)
C8 N1 C1 C6 -0.9(3)
C22 N1 C1 C6 173.8(3)
N1 C1 C2 C3 179.5(3)
C6 C1 C2 C3 -0.2(5)
C1 C2 C3 C4 -2.0(5)
C2 C3 C4 C5 3.0(6)
C3 C4 C5 C6 -1.7(6)
C4 C5 C6 C1 -0.5(5)
C4 C5 C6 C7 -179.9(3)
N1 C1 C6 C5 -178.3(3)
C2 C1 C6 C5 1.4(5)
N1 C1 C6 C7 1.2(3)
C2 C1 C6 C7 -179.1(3)
C5 C6 C7 C8 178.4(4)
C1 C6 C7 C8 -1.1(3)
C5 C6 C7 C9 -2.9(6)
C1 C6 C7 C9 177.6(3)
C11 O1 C8 N1 -179.4(3)
C11 O1 C8 C7 -1.0(4)
C1 N1 C8 O1 178.9(3)
C22 N1 C8 O1 4.0(4)
C1 N1 C8 C7 0.2(3)
C22 N1 C8 C7 -174.7(3)
C6 C7 C8 O1 -177.9(3)
C9 C7 C8 O1 3.1(5)
C6 C7 C8 N1 0.6(4)
C9 C7 C8 N1 -178.4(3)
C8 C7 C9 C10 -2.5(4)
C6 C7 C9 C10 179.0(3)
C8 C7 C9 C16 117.9(3)
C6 C7 C9 C16 -60.6(4)
C8 C7 C9 C19 -122.9(3)
C6 C7 C9 C19 58.6(5)
C7 C9 C10 C11 0.2(4)
C16 C9 C10 C11 -119.6(3)
C19 C9 C10 C11 121.5(3)
C9 C10 C11 O1 1.8(5)
C9 C10 C11 C12 -179.0(3)
C8 O1 C11 C10 -1.5(4)
C8 O1 C11 C12 179.2(2)
C10 C11 C12 C13 116.3(4)
O1 C11 C12 C13 -64.5(3)
C14 O3 C13 O2 0.3(5)
C14 O3 C13 C12 -178.6(3)
C11 C12 C13 O2 151.1(4)
C11 C12 C13 O3 -30.0(4)
C13 O3 C14 C15 80.7(4)
C17 O5 C16 O4 -2.7(6)
C17 O5 C16 C9 179.2(4)
C10 C9 C16 O4 24.5(4)
C7 C9 C16 O4 -95.0(4)
C19 C9 C16 O4 144.2(3)
C10 C9 C16 O5 -157.5(3)
C7 C9 C16 O5 83.0(3)
C19 C9 C16 O5 -37.8(3)
C16 O5 C17 C18 -160.5(6)
C20 O7 C19 O6 -8.1(5)
C20 O7 C19 C9 175.5(3)
C10 C9 C19 O6 -113.8(4)
C7 C9 C19 O6 6.2(5)
C16 C9 C19 O6 126.1(4)
C10 C9 C19 O7 62.7(3)
C7 C9 C19 O7 -177.3(3)
C16 C9 C19 O7 -57.4(3)
C19 O7 C20 C21 174.2(3)
C8 N1 C22 C23 89.7(4)
C1 N1 C22 C23 -84.1(4)
N1 C22 C23 C28 -69.4(4)
N1 C22 C23 C24 107.7(4)
C28 C23 C24 C25 -0.6(6)
C22 C23 C24 C25 -177.9(3)
C23 C24 C25 C26 1.0(7)
C24 C25 C26 C27 -0.4(7)
C25 C26 C27 C28 -0.4(7)
C24 C23 C28 C27 -0.2(5)
C22 C23 C28 C27 177.1(3)
C26 C27 C28 C23 0.7(6)
|
1501985.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501985.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501985
loop_
_publ_author_name
'Zhang, Xiu-Chun'
'Cao, Shu-Hua'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
Phosphine- and nitrogen-containing Lewis base catalyzed highly
regioselective and geometric selective cyclization of isatin derived
electron-deficient alkenes with ethyl 2,3-butadienoate.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1142
_journal_page_last 1145
_journal_paper_doi 10.1021/ol1031798
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_sum 'C22 H25 N O7'
_chemical_formula_weight 415.43
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 96.626(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 13.776(2)
_cell_length_b 8.3633(13)
_cell_length_c 18.579(3)
_cell_measurement_reflns_used 9879
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 54.208
_cell_measurement_theta_min 4.414
_cell_volume 2126.2(6)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0174
_diffrn_reflns_av_sigmaI/netI 0.0217
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 15364
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 1.49
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_T_max 0.7455
_exptl_absorpt_correction_T_min 0.6686
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.298
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 880
_exptl_crystal_size_max 0.357
_exptl_crystal_size_mid 0.288
_exptl_crystal_size_min 0.176
_refine_diff_density_max 0.889
_refine_diff_density_min -0.531
_refine_diff_density_rms 0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.7(9)
_refine_ls_extinction_coef 0.0105(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 570
_refine_ls_number_reflns 7493
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.077
_refine_ls_R_factor_all 0.0533
_refine_ls_R_factor_gt 0.0518
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+1.0328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1472
_refine_ls_wR_factor_ref 0.1495
_reflns_number_gt 7259
_reflns_number_total 7493
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031798_si_004.cif
_cod_data_source_block dm10102
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_database_code 1501985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.74775(17) -0.1213(3) 0.18627(12) 0.0415(5) Uani 1 1 d . . .
N2 N 0.85839(17) 0.3758(3) 0.26941(11) 0.0375(5) Uani 1 1 d . . .
O1 O 0.59548(14) 0.0027(3) 0.17716(10) 0.0416(5) Uani 1 1 d . . .
O2 O 0.5018(3) 0.1120(5) 0.29204(14) 0.0907(10) Uani 1 1 d . . .
O3 O 0.3675(3) 0.2603(4) 0.25482(14) 0.0772(9) Uani 1 1 d . . .
O4 O 0.66368(16) -0.0391(3) -0.06808(10) 0.0487(5) Uani 1 1 d . . .
O5 O 0.6007(2) 0.2067(3) -0.08599(10) 0.0633(7) Uani 1 1 d . . .
O6 O 0.61239(15) 0.4024(3) 0.06509(11) 0.0440(5) Uani 1 1 d . . .
O7 O 0.75781(14) 0.3302(2) 0.03179(11) 0.0433(5) Uani 1 1 d . . .
O8 O 0.80358(14) 0.4995(2) 0.36911(9) 0.0374(4) Uani 1 1 d . A .
O9 O 0.61577(15) 0.5950(3) 0.37235(11) 0.0504(5) Uani 1 1 d . A .
O10 O 0.60255(15) 0.7983(3) 0.44903(10) 0.0457(5) Uani 1 1 d . A .
O11 O 0.95505(16) 0.9020(3) 0.38985(12) 0.0511(5) Uani 1 1 d . . .
O12 O 1.08451(16) 0.8155(3) 0.33751(13) 0.0522(5) Uani 1 1 d . . .
O13 O 1.14807(16) 0.4563(3) 0.43306(11) 0.0491(5) Uani 1 1 d . . .
O14 O 1.1366(2) 0.6908(4) 0.48978(18) 0.0849(12) Uani 1 1 d D . .
C1 C 0.8255(2) -0.1307(4) 0.14649(15) 0.0427(6) Uani 1 1 d . . .
C2 C 0.9134(2) -0.2139(4) 0.16244(19) 0.0526(8) Uani 1 1 d . . .
H2 H 0.9266 -0.2747 0.2057 0.063 Uiso 1 1 calc R . .
C3 C 0.9801(2) -0.2040(5) 0.1128(2) 0.0650(10) Uani 1 1 d . . .
H3 H 1.0406 -0.2589 0.1222 0.078 Uiso 1 1 calc R . .
C4 C 0.9609(2) -0.1152(5) 0.0489(2) 0.0629(9) Uani 1 1 d . . .
H4 H 1.0088 -0.1109 0.0160 0.075 Uiso 1 1 calc R . .
C5 C 0.8736(2) -0.0333(4) 0.03271(16) 0.0488(7) Uani 1 1 d . . .
H5 H 0.8613 0.0272 -0.0106 0.059 Uiso 1 1 calc R . .
C6 C 0.8037(2) -0.0421(4) 0.08179(14) 0.0397(6) Uani 1 1 d . . .
C7 C 0.70751(19) 0.0213(3) 0.08374(13) 0.0335(5) Uani 1 1 d . . .
C8 C 0.6786(2) -0.0299(3) 0.14703(14) 0.0366(6) Uani 1 1 d . . .
C9 C 0.63920(19) 0.1267(3) 0.03522(12) 0.0331(5) Uani 1 1 d . . .
C10 C 0.53482(18) 0.0968(3) 0.05519(13) 0.0366(6) Uani 1 1 d . . .
H10A H 0.4907 0.1802 0.0321 0.044 Uiso 1 1 calc R . .
H10B H 0.5115 -0.0079 0.0352 0.044 Uiso 1 1 calc R . .
C11 C 0.52871(19) 0.0979(3) 0.13528(14) 0.0366(6) Uani 1 1 d . . .
C12 C 0.4607(2) 0.1763(4) 0.16678(15) 0.0430(6) Uani 1 1 d . . .
H12 H 0.4148 0.2372 0.1360 0.052 Uiso 1 1 calc R . .
C13 C 0.4500(3) 0.1775(4) 0.24500(18) 0.0588(9) Uani 1 1 d . . .
C14 C 0.3400(3) 0.2756(6) 0.3281(2) 0.0704(10) Uani 1 1 d . . .
H14A H 0.3697 0.1879 0.3590 0.084 Uiso 1 1 calc R . .
H14B H 0.2681 0.2686 0.3270 0.084 Uiso 1 1 calc R . .
C15 C 0.3745(4) 0.4303(7) 0.3579(2) 0.0892(15) Uani 1 1 d . . .
H15A H 0.4460 0.4337 0.3619 0.134 Uiso 1 1 calc R . .
H15B H 0.3531 0.4445 0.4060 0.134 Uiso 1 1 calc R . .
H15C H 0.3474 0.5162 0.3258 0.134 Uiso 1 1 calc R . .
C16 C 0.6378(2) 0.0839(4) -0.04588(14) 0.0386(6) Uani 1 1 d . . .
C17 C 0.5895(4) 0.1828(6) -0.16546(17) 0.0733(12) Uani 1 1 d . . .
H17A H 0.5965 0.2866 -0.1900 0.088 Uiso 1 1 calc R . .
H17B H 0.6413 0.1101 -0.1788 0.088 Uiso 1 1 calc R . .
C18 C 0.4971(3) 0.1170(6) -0.1882(2) 0.0732(11) Uani 1 1 d . . .
H18A H 0.4941 0.0077 -0.1696 0.110 Uiso 1 1 calc R . .
H18B H 0.4866 0.1150 -0.2413 0.110 Uiso 1 1 calc R . .
H18C H 0.4464 0.1822 -0.1697 0.110 Uiso 1 1 calc R . .
C19 C 0.66565(18) 0.3035(3) 0.04564(12) 0.0317(5) Uani 1 1 d . . .
C20 C 0.7897(2) 0.4967(4) 0.03340(19) 0.0521(7) Uani 1 1 d . . .
H20A H 0.8607 0.5026 0.0495 0.063 Uiso 1 1 calc R . .
H20B H 0.7549 0.5577 0.0682 0.063 Uiso 1 1 calc R . .
C21 C 0.7686(3) 0.5681(5) -0.0407(2) 0.0630(10) Uani 1 1 d . . .
H21A H 0.8093 0.5159 -0.0737 0.095 Uiso 1 1 calc R . .
H21B H 0.7831 0.6828 -0.0384 0.095 Uiso 1 1 calc R . .
H21C H 0.6995 0.5521 -0.0584 0.095 Uiso 1 1 calc R . .
C22 C 0.7407(3) -0.1884(5) 0.25796(18) 0.0588(9) Uani 1 1 d . . .
H22A H 0.6861 -0.1383 0.2789 0.088 Uiso 1 1 calc R . .
H22B H 0.8016 -0.1681 0.2893 0.088 Uiso 1 1 calc R . .
H22C H 0.7296 -0.3040 0.2538 0.088 Uiso 1 1 calc R . .
C23 C 0.9444(2) 0.3680(3) 0.23678(14) 0.0378(6) Uani 1 1 d . . .
C24 C 0.9612(2) 0.2891(4) 0.17346(15) 0.0463(7) Uani 1 1 d . . .
H24 H 0.9117 0.2273 0.1466 0.056 Uiso 1 1 calc R . .
C25 C 1.0537(2) 0.3048(5) 0.15146(16) 0.0525(8) Uani 1 1 d . . .
H25 H 1.0678 0.2535 0.1083 0.063 Uiso 1 1 calc R . .
C26 C 1.1262(2) 0.3946(5) 0.19158(17) 0.0541(8) Uani 1 1 d . . .
H26 H 1.1888 0.4029 0.1751 0.065 Uiso 1 1 calc R . .
C27 C 1.1091(2) 0.4718(4) 0.25477(16) 0.0459(7) Uani 1 1 d . . .
H27 H 1.1591 0.5334 0.2812 0.055 Uiso 1 1 calc R . .
C28 C 1.01744(19) 0.4576(3) 0.27903(13) 0.0362(5) Uani 1 1 d . . .
C29 C 0.97265(19) 0.5191(3) 0.33970(12) 0.0340(5) Uani 1 1 d . A .
C30 C 0.87877(19) 0.4675(3) 0.32990(12) 0.0326(5) Uani 1 1 d . . .
C31 C 1.00563(19) 0.6251(3) 0.40332(13) 0.0358(6) Uani 1 1 d . . .
C32 C 0.9316(2) 0.6051(4) 0.45937(13) 0.0384(6) Uani 1 1 d . A .
H32A H 0.9463 0.5043 0.4864 0.046 Uiso 1 1 calc R . .
H32B H 0.9407 0.6941 0.4946 0.046 Uiso 1 1 calc R . .
C33 C 0.8263(2) 0.6021(3) 0.42684(12) 0.0359(5) Uani 1 1 d . . .
C34 C 0.7546(2) 0.6818(4) 0.45238(13) 0.0389(6) Uani 1 1 d . A .
H34 H 0.7705 0.7432 0.4951 0.047 Uiso 1 1 calc R . .
C35 C 0.6524(2) 0.6825(3) 0.41947(13) 0.0379(6) Uani 1 1 d . . .
C36 C 0.5007(2) 0.8201(4) 0.41798(16) 0.0484(7) Uani 1 1 d . . .
H36A H 0.4636 0.7197 0.4216 0.058 Uiso 1 1 calc R A .
H36B H 0.4977 0.8501 0.3662 0.058 Uiso 1 1 calc R . .
C37 C 0.4586(3) 0.9490(5) 0.45942(19) 0.0612(9) Uani 1 1 d . A .
H37A H 0.4634 0.9191 0.5107 0.092 Uiso 1 1 calc R . .
H37B H 0.3898 0.9646 0.4407 0.092 Uiso 1 1 calc R . .
H37C H 0.4947 1.0485 0.4543 0.092 Uiso 1 1 calc R . .
C38 C 1.01103(19) 0.7983(3) 0.37777(13) 0.0369(6) Uani 1 1 d . A .
C39 C 1.0969(3) 0.9724(5) 0.3057(2) 0.0619(9) Uani 1 1 d . . .
H39A H 1.1106 1.0543 0.3440 0.074 Uiso 1 1 calc R . .
H39B H 1.0373 1.0038 0.2739 0.074 Uiso 1 1 calc R . .
C40 C 1.1826(4) 0.9552(7) 0.2624(3) 0.0844(13) Uani 1 1 d . . .
H40A H 1.2416 0.9301 0.2951 0.127 Uiso 1 1 calc R . .
H40B H 1.1923 1.0557 0.2370 0.127 Uiso 1 1 calc R . .
H40C H 1.1695 0.8688 0.2270 0.127 Uiso 1 1 calc R . .
C41 C 1.1066(2) 0.5770(4) 0.44242(15) 0.0439(7) Uani 1 1 d . A .
C44 C 0.7633(2) 0.3115(5) 0.24099(16) 0.0520(8) Uani 1 1 d . . .
H44A H 0.7157 0.3349 0.2749 0.078 Uiso 1 1 calc R . .
H44B H 0.7684 0.1955 0.2350 0.078 Uiso 1 1 calc R . .
H44C H 0.7419 0.3608 0.1940 0.078 Uiso 1 1 calc R . .
C42 C 1.2473(6) 0.6882(8) 0.5191(3) 0.0420(18) Uani 0.568(15) 1 d PD A 1
H42A H 1.2860 0.6234 0.4881 0.050 Uiso 0.568(15) 1 calc PR A 1
H42B H 1.2752 0.7972 0.5246 0.050 Uiso 0.568(15) 1 calc PR A 1
C43 C 1.2398(5) 0.6102(8) 0.5906(5) 0.048(2) Uani 0.568(15) 1 d P A 1
H43A H 1.1980 0.6750 0.6185 0.071 Uiso 0.568(15) 1 calc PR A 1
H43B H 1.3051 0.6012 0.6176 0.071 Uiso 0.568(15) 1 calc PR A 1
H43C H 1.2114 0.5034 0.5828 0.071 Uiso 0.568(15) 1 calc PR A 1
C42' C 1.2051(6) 0.6311(8) 0.5544(5) 0.037(2) Uani 0.432(15) 1 d PD A 2
H42C H 1.1859 0.6711 0.6009 0.044 Uiso 0.432(15) 1 calc PR A 2
H42D H 1.2091 0.5130 0.5557 0.044 Uiso 0.432(15) 1 calc PR A 2
C43' C 1.2979(9) 0.7052(10) 0.5368(5) 0.047(2) Uani 0.432(15) 1 d P A 2
H43D H 1.3168 0.6572 0.4924 0.070 Uiso 0.432(15) 1 calc PR A 2
H43E H 1.3495 0.6867 0.5768 0.070 Uiso 0.432(15) 1 calc PR A 2
H43F H 1.2883 0.8205 0.5296 0.070 Uiso 0.432(15) 1 calc PR A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0492(12) 0.0309(13) 0.0400(11) 0.0091(10) -0.0141(10) -0.0023(10)
N2 0.0501(12) 0.0304(12) 0.0297(10) -0.0048(9) -0.0049(9) -0.0038(10)
O1 0.0464(10) 0.0373(11) 0.0391(9) 0.0120(8) -0.0038(8) -0.0019(8)
O2 0.133(3) 0.092(2) 0.0482(14) 0.0193(16) 0.0141(15) 0.027(2)
O3 0.123(2) 0.0555(17) 0.0578(14) 0.0087(12) 0.0300(15) 0.0329(16)
O4 0.0621(12) 0.0419(12) 0.0377(9) -0.0105(9) -0.0124(9) 0.0117(10)
O5 0.115(2) 0.0439(13) 0.0265(9) 0.0016(9) -0.0115(11) 0.0209(14)
O6 0.0518(11) 0.0302(11) 0.0495(11) 0.0000(9) 0.0038(9) -0.0001(9)
O7 0.0474(10) 0.0280(11) 0.0544(11) -0.0002(8) 0.0050(8) -0.0033(8)
O8 0.0499(10) 0.0300(10) 0.0313(8) -0.0044(7) 0.0006(7) -0.0073(8)
O9 0.0519(11) 0.0558(14) 0.0434(11) -0.0154(10) 0.0044(9) -0.0093(10)
O10 0.0510(11) 0.0416(12) 0.0438(10) -0.0071(9) 0.0022(8) -0.0027(9)
O11 0.0573(12) 0.0305(11) 0.0640(13) 0.0018(10) 0.0010(10) 0.0087(10)
O12 0.0514(11) 0.0318(12) 0.0732(14) 0.0034(10) 0.0064(10) -0.0016(9)
O13 0.0606(12) 0.0398(12) 0.0416(10) -0.0047(9) -0.0170(9) 0.0167(10)
O14 0.0844(19) 0.0640(18) 0.096(2) -0.0510(17) -0.0650(18) 0.0445(16)
C1 0.0499(15) 0.0274(15) 0.0455(14) -0.0003(11) -0.0167(12) -0.0051(11)
C2 0.0517(16) 0.0383(17) 0.0612(18) 0.0010(14) -0.0217(14) 0.0040(13)
C3 0.0454(16) 0.060(2) 0.082(2) -0.011(2) -0.0235(16) 0.0128(16)
C4 0.0450(16) 0.072(3) 0.069(2) -0.0138(19) -0.0052(14) 0.0009(16)
C5 0.0476(15) 0.0501(19) 0.0460(14) -0.0054(14) -0.0055(12) -0.0028(14)
C6 0.0458(13) 0.0285(13) 0.0409(13) -0.0021(11) -0.0123(11) -0.0038(12)
C7 0.0406(12) 0.0240(12) 0.0326(11) -0.0010(10) -0.0095(10) -0.0020(10)
C8 0.0457(13) 0.0238(13) 0.0361(12) 0.0056(10) -0.0134(10) -0.0049(11)
C9 0.0450(13) 0.0261(13) 0.0249(10) 0.0022(9) -0.0101(9) -0.0008(10)
C10 0.0414(13) 0.0311(14) 0.0340(12) 0.0017(11) -0.0094(10) -0.0056(11)
C11 0.0451(13) 0.0246(13) 0.0372(12) 0.0039(10) -0.0080(10) -0.0088(11)
C12 0.0589(16) 0.0300(15) 0.0389(14) 0.0029(11) 0.0006(12) -0.0013(13)
C13 0.095(3) 0.0380(18) 0.0440(16) 0.0104(14) 0.0092(16) 0.0051(18)
C14 0.069(2) 0.069(3) 0.073(2) 0.004(2) 0.0096(18) 0.0039(19)
C15 0.108(3) 0.102(4) 0.056(2) -0.025(2) 0.000(2) -0.018(3)
C16 0.0465(13) 0.0361(16) 0.0305(12) -0.0010(11) -0.0070(10) -0.0010(12)
C17 0.115(3) 0.063(3) 0.0349(15) -0.0025(15) -0.0213(17) 0.013(2)
C18 0.096(3) 0.064(3) 0.0565(19) -0.0018(19) -0.0058(19) 0.012(2)
C19 0.0399(12) 0.0291(13) 0.0235(10) 0.0037(9) -0.0072(9) 0.0001(11)
C20 0.0554(17) 0.0325(17) 0.0685(19) -0.0035(14) 0.0073(14) -0.0131(13)
C21 0.0567(18) 0.041(2) 0.090(3) 0.0217(17) 0.0034(18) -0.0058(15)
C22 0.0612(18) 0.058(2) 0.0528(17) 0.0275(17) -0.0111(14) -0.0022(17)
C23 0.0498(14) 0.0287(14) 0.0323(12) 0.0014(10) -0.0060(10) 0.0044(11)
C24 0.0638(17) 0.0371(16) 0.0349(13) -0.0052(12) -0.0066(12) 0.0071(14)
C25 0.0641(18) 0.054(2) 0.0387(14) -0.0050(14) 0.0049(13) 0.0198(16)
C26 0.0545(17) 0.056(2) 0.0514(16) -0.0016(15) 0.0036(13) 0.0164(16)
C27 0.0430(14) 0.0434(18) 0.0492(15) -0.0018(13) -0.0037(12) 0.0076(13)
C28 0.0454(13) 0.0269(13) 0.0333(11) 0.0011(10) -0.0075(10) 0.0092(11)
C29 0.0469(13) 0.0240(12) 0.0279(11) -0.0002(9) -0.0092(10) 0.0028(10)
C30 0.0458(13) 0.0247(12) 0.0256(10) 0.0000(9) -0.0036(9) -0.0016(10)
C31 0.0457(13) 0.0254(13) 0.0320(11) -0.0034(10) -0.0133(10) 0.0035(11)
C32 0.0558(15) 0.0298(14) 0.0267(11) -0.0016(10) -0.0082(10) 0.0010(12)
C33 0.0571(15) 0.0247(13) 0.0245(10) 0.0026(10) -0.0016(10) -0.0070(11)
C34 0.0556(15) 0.0318(14) 0.0289(11) 0.0008(10) 0.0035(10) -0.0085(12)
C35 0.0499(14) 0.0331(15) 0.0318(12) 0.0007(10) 0.0087(10) -0.0079(12)
C36 0.0502(15) 0.0490(19) 0.0454(15) -0.0013(14) 0.0029(12) -0.0015(14)
C37 0.0619(19) 0.061(2) 0.0598(19) -0.0029(17) 0.0037(15) 0.0115(17)
C38 0.0425(13) 0.0265(13) 0.0376(12) -0.0011(11) -0.0124(10) 0.0018(11)
C39 0.068(2) 0.0376(19) 0.080(2) 0.0080(17) 0.0092(17) -0.0098(16)
C40 0.087(3) 0.071(3) 0.097(3) 0.016(3) 0.018(2) -0.020(2)
C41 0.0493(15) 0.0365(16) 0.0409(14) -0.0064(11) -0.0168(12) 0.0103(12)
C44 0.0550(16) 0.055(2) 0.0431(15) -0.0171(15) -0.0061(12) -0.0159(15)
C42 0.033(4) 0.049(3) 0.043(3) 0.002(3) -0.001(3) -0.001(3)
C43 0.053(3) 0.041(3) 0.046(4) -0.006(3) -0.011(3) 0.004(3)
C42' 0.042(4) 0.026(3) 0.036(4) -0.003(3) -0.020(4) 0.001(3)
C43' 0.031(5) 0.048(4) 0.059(5) -0.010(3) 0.000(4) 0.001(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C1 106.5(2)
C8 N1 C22 126.0(3)
C1 N1 C22 127.5(3)
C30 N2 C23 106.3(2)
C30 N2 C44 126.7(2)
C23 N2 C44 126.8(2)
C8 O1 C11 114.9(2)
C13 O3 C14 118.7(3)
C16 O5 C17 116.2(3)
C19 O7 C20 116.4(2)
C30 O8 C33 114.8(2)
C35 O10 C36 116.2(2)
C38 O12 C39 117.2(2)
C41 O14 C42' 113.8(3)
C41 O14 C42 116.0(3)
C42' O14 C42 39.5(3)
N1 C1 C2 128.7(3)
N1 C1 C6 109.0(2)
C2 C1 C6 122.3(3)
C3 C2 C1 117.2(3)
C3 C2 H2 121.4
C1 C2 H2 121.4
C2 C3 C4 121.7(3)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 121.3(3)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 118.5(3)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 119.1(3)
C5 C6 C7 134.7(3)
C1 C6 C7 106.2(2)
C8 C7 C6 105.7(2)
C8 C7 C9 118.6(2)
C6 C7 C9 135.7(2)
C7 C8 O1 129.8(2)
C7 C8 N1 112.6(3)
O1 C8 N1 117.5(2)
C7 C9 C19 111.45(19)
C7 C9 C10 107.2(2)
C19 C9 C10 109.9(2)
C7 C9 C16 112.5(2)
C19 C9 C16 108.9(2)
C10 C9 C16 106.79(19)
C11 C10 C9 113.4(2)
C11 C10 H10A 108.9
C9 C10 H10A 108.9
C11 C10 H10B 108.9
C9 C10 H10B 108.9
H10A C10 H10B 107.7
C12 C11 O1 119.4(2)
C12 C11 C10 124.1(2)
O1 C11 C10 116.3(2)
C11 C12 C13 126.2(3)
C11 C12 H12 116.9
C13 C12 H12 116.9
O2 C13 O3 124.9(3)
O2 C13 C12 126.6(4)
O3 C13 C12 108.4(3)
O3 C14 C15 108.8(4)
O3 C14 H14A 109.9
C15 C14 H14A 109.9
O3 C14 H14B 109.9
C15 C14 H14B 109.9
H14A C14 H14B 108.3
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O4 C16 O5 126.0(2)
O4 C16 C9 125.0(2)
O5 C16 C9 109.0(2)
C18 C17 O5 109.8(4)
C18 C17 H17A 109.7
O5 C17 H17A 109.7
C18 C17 H17B 109.7
O5 C17 H17B 109.7
H17A C17 H17B 108.2
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O6 C19 O7 124.9(3)
O6 C19 C9 124.4(2)
O7 C19 C9 110.7(2)
O7 C20 C21 109.6(3)
O7 C20 H20A 109.8
C21 C20 H20A 109.8
O7 C20 H20B 109.8
C21 C20 H20B 109.8
H20A C20 H20B 108.2
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 H22A 109.5
N1 C22 H22B 109.5
H22A C22 H22B 109.5
N1 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
N2 C23 C24 128.5(3)
N2 C23 C28 108.6(2)
C24 C23 C28 122.8(3)
C25 C24 C23 116.8(3)
C25 C24 H24 121.6
C23 C24 H24 121.6
C24 C25 C26 121.2(3)
C24 C25 H25 119.4
C26 C25 H25 119.4
C27 C26 C25 121.5(3)
C27 C26 H26 119.2
C25 C26 H26 119.2
C26 C27 C28 118.9(3)
C26 C27 H27 120.5
C28 C27 H27 120.5
C27 C28 C23 118.5(2)
C27 C28 C29 135.1(3)
C23 C28 C29 106.3(2)
C30 C29 C28 105.6(2)
C30 C29 C31 119.3(2)
C28 C29 C31 135.0(3)
C29 C30 O8 129.7(2)
C29 C30 N2 113.1(2)
O8 C30 N2 117.1(2)
C29 C31 C38 109.6(2)
C29 C31 C41 112.9(2)
C38 C31 C41 108.6(2)
C29 C31 C32 107.6(2)
C38 C31 C32 111.8(2)
C41 C31 C32 106.4(2)
C33 C32 C31 114.24(19)
C33 C32 H32A 108.7
C31 C32 H32A 108.7
C33 C32 H32B 108.7
C31 C32 H32B 108.7
H32A C32 H32B 107.6
C34 C33 O8 118.6(2)
C34 C33 C32 124.8(2)
O8 C33 C32 116.4(2)
C33 C34 C35 124.9(2)
C33 C34 H34 117.6
C35 C34 H34 117.6
O9 C35 O10 123.0(3)
O9 C35 C34 126.9(3)
O10 C35 C34 110.1(2)
O10 C36 C37 107.5(3)
O10 C36 H36A 110.2
C37 C36 H36A 110.2
O10 C36 H36B 110.2
C37 C36 H36B 110.2
H36A C36 H36B 108.5
C36 C37 H37A 109.5
C36 C37 H37B 109.5
H37A C37 H37B 109.5
C36 C37 H37C 109.5
H37A C37 H37C 109.5
H37B C37 H37C 109.5
O11 C38 O12 124.9(3)
O11 C38 C31 124.9(3)
O12 C38 C31 110.1(2)
O12 C39 C40 105.4(3)
O12 C39 H39A 110.7
C40 C39 H39A 110.7
O12 C39 H39B 110.7
C40 C39 H39B 110.7
H39A C39 H39B 108.8
C39 C40 H40A 109.5
C39 C40 H40B 109.5
H40A C40 H40B 109.5
C39 C40 H40C 109.5
H40A C40 H40C 109.5
H40B C40 H40C 109.5
O13 C41 O14 126.1(3)
O13 C41 C31 125.2(3)
O14 C41 C31 108.6(2)
N2 C44 H44A 109.5
N2 C44 H44B 109.5
H44A C44 H44B 109.5
N2 C44 H44C 109.5
H44A C44 H44C 109.5
H44B C44 H44C 109.5
C43 C42 O14 98.7(6)
C43 C42 H42A 112.0
O14 C42 H42A 112.0
C43 C42 H42B 112.0
O14 C42 H42B 112.0
H42A C42 H42B 109.7
C43' C42' O14 99.2(8)
C43' C42' H42C 111.9
O14 C42' H42C 111.9
C43' C42' H42D 111.9
O14 C42' H42D 111.9
H42C C42' H42D 109.6
C42' C43' H43D 109.5
C42' C43' H43E 109.5
H43D C43' H43E 109.5
C42' C43' H43F 109.5
H43D C43' H43F 109.5
H43E C43' H43F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.364(3)
N1 C1 1.372(4)
N1 C22 1.459(4)
N2 C30 1.363(3)
N2 C23 1.393(4)
N2 C44 1.457(4)
O1 C8 1.359(4)
O1 C11 1.386(3)
O2 C13 1.196(5)
O3 C13 1.361(5)
O3 C14 1.461(5)
O4 C16 1.178(4)
O5 C16 1.335(4)
O5 C17 1.480(4)
O6 C19 1.189(3)
O7 C19 1.343(3)
O7 C20 1.459(4)
O8 C30 1.360(3)
O8 C33 1.381(3)
O9 C35 1.206(3)
O10 C35 1.341(4)
O10 C36 1.465(4)
O11 C38 1.199(4)
O12 C38 1.334(4)
O12 C39 1.457(4)
O13 C41 1.182(4)
O14 C41 1.329(4)
O14 C42' 1.523(9)
O14 C42 1.560(9)
C1 C2 1.399(4)
C1 C6 1.415(4)
C2 C3 1.376(6)
C2 H2 0.9500
C3 C4 1.400(6)
C3 H3 0.9500
C4 C5 1.387(5)
C4 H4 0.9500
C5 C6 1.402(4)
C5 H5 0.9500
C6 C7 1.432(4)
C7 C8 1.354(4)
C7 C9 1.510(3)
C9 C19 1.530(4)
C9 C10 1.546(4)
C9 C16 1.547(3)
C10 C11 1.500(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.333(4)
C12 C13 1.477(4)
C12 H12 0.9500
C14 C15 1.465(7)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C17 C18 1.406(6)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C20 C21 1.497(5)
C20 H20A 0.9900
C20 H20B 0.9900
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 C24 1.392(4)
C23 C28 1.417(4)
C24 C25 1.389(5)
C24 H24 0.9500
C25 C26 1.395(5)
C25 H25 0.9500
C26 C27 1.383(4)
C26 H26 0.9500
C27 C28 1.394(4)
C27 H27 0.9500
C28 C29 1.441(4)
C29 C30 1.356(4)
C29 C31 1.505(3)
C31 C38 1.529(4)
C31 C41 1.546(3)
C31 C32 1.549(4)
C32 C33 1.505(4)
C32 H32A 0.9900
C32 H32B 0.9900
C33 C34 1.324(4)
C34 C35 1.469(4)
C34 H34 0.9500
C36 C37 1.481(5)
C36 H36A 0.9900
C36 H36B 0.9900
C37 H37A 0.9800
C37 H37B 0.9800
C37 H37C 0.9800
C39 C40 1.510(6)
C39 H39A 0.9900
C39 H39B 0.9900
C40 H40A 0.9800
C40 H40B 0.9800
C40 H40C 0.9800
C44 H44A 0.9800
C44 H44B 0.9800
C44 H44C 0.9800
C42 C43 1.495(10)
C42 H42A 0.9900
C42 H42B 0.9900
C43 H43A 0.9800
C43 H43B 0.9800
C43 H43C 0.9800
C42' C43' 1.491(13)
C42' H42C 0.9900
C42' H42D 0.9900
C43' H43D 0.9800
C43' H43E 0.9800
C43' H43F 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N1 C1 C2 -178.3(3)
C22 N1 C1 C2 4.3(5)
C8 N1 C1 C6 0.5(3)
C22 N1 C1 C6 -176.9(3)
N1 C1 C2 C3 179.8(3)
C6 C1 C2 C3 1.2(5)
C1 C2 C3 C4 -0.2(5)
C2 C3 C4 C5 -0.2(6)
C3 C4 C5 C6 -0.4(5)
C4 C5 C6 C1 1.3(4)
C4 C5 C6 C7 -178.8(3)
N1 C1 C6 C5 179.3(3)
C2 C1 C6 C5 -1.8(4)
N1 C1 C6 C7 -0.5(3)
C2 C1 C6 C7 178.3(3)
C5 C6 C7 C8 -179.5(3)
C1 C6 C7 C8 0.4(3)
C5 C6 C7 C9 -1.1(5)
C1 C6 C7 C9 178.7(3)
C6 C7 C8 O1 176.3(3)
C9 C7 C8 O1 -2.4(4)
C6 C7 C8 N1 -0.1(3)
C9 C7 C8 N1 -178.8(2)
C11 O1 C8 C7 2.8(4)
C11 O1 C8 N1 179.1(2)
C1 N1 C8 C7 -0.3(3)
C22 N1 C8 C7 177.2(3)
C1 N1 C8 O1 -177.2(2)
C22 N1 C8 O1 0.3(4)
C8 C7 C9 C19 97.8(3)
C6 C7 C9 C19 -80.4(4)
C8 C7 C9 C10 -22.5(3)
C6 C7 C9 C10 159.3(3)
C8 C7 C9 C16 -139.6(3)
C6 C7 C9 C16 42.2(4)
C7 C9 C10 C11 46.5(3)
C19 C9 C10 C11 -74.8(3)
C16 C9 C10 C11 167.3(2)
C8 O1 C11 C12 -159.7(3)
C8 O1 C11 C10 24.0(3)
C9 C10 C11 C12 133.5(3)
C9 C10 C11 O1 -50.4(3)
O1 C11 C12 C13 2.3(5)
C10 C11 C12 C13 178.2(3)
C14 O3 C13 O2 1.6(6)
C14 O3 C13 C12 178.8(3)
C11 C12 C13 O2 2.0(6)
C11 C12 C13 O3 -175.1(3)
C13 O3 C14 C15 97.3(5)
C17 O5 C16 O4 1.5(5)
C17 O5 C16 C9 -177.1(3)
C7 C9 C16 O4 19.7(4)
C19 C9 C16 O4 143.7(3)
C10 C9 C16 O4 -97.6(3)
C7 C9 C16 O5 -161.7(2)
C19 C9 C16 O5 -37.7(3)
C10 C9 C16 O5 81.0(3)
C16 O5 C17 C18 89.4(4)
C20 O7 C19 O6 -7.0(4)
C20 O7 C19 C9 174.7(2)
C7 C9 C19 O6 -119.8(3)
C10 C9 C19 O6 -1.2(3)
C16 C9 C19 O6 115.5(3)
C7 C9 C19 O7 58.4(3)
C10 C9 C19 O7 177.11(18)
C16 C9 C19 O7 -66.2(2)
C19 O7 C20 C21 -90.4(3)
C30 N2 C23 C24 -179.8(3)
C44 N2 C23 C24 -5.0(5)
C30 N2 C23 C28 -0.1(3)
C44 N2 C23 C28 174.7(3)
N2 C23 C24 C25 178.0(3)
C28 C23 C24 C25 -1.7(4)
C23 C24 C25 C26 0.6(5)
C24 C25 C26 C27 -0.1(5)
C25 C26 C27 C28 0.7(5)
C26 C27 C28 C23 -1.7(4)
C26 C27 C28 C29 -179.2(3)
N2 C23 C28 C27 -177.4(2)
C24 C23 C28 C27 2.3(4)
N2 C23 C28 C29 0.7(3)
C24 C23 C28 C29 -179.5(3)
C27 C28 C29 C30 176.6(3)
C23 C28 C29 C30 -1.1(3)
C27 C28 C29 C31 -0.2(5)
C23 C28 C29 C31 -177.9(3)
C28 C29 C30 O8 -175.7(3)
C31 C29 C30 O8 1.7(4)
C28 C29 C30 N2 1.1(3)
C31 C29 C30 N2 178.6(2)
C33 O8 C30 C29 1.1(4)
C33 O8 C30 N2 -175.6(2)
C23 N2 C30 C29 -0.7(3)
C44 N2 C30 C29 -175.5(3)
C23 N2 C30 O8 176.6(2)
C44 N2 C30 O8 1.8(4)
C30 C29 C31 C38 -102.4(3)
C28 C29 C31 C38 74.2(4)
C30 C29 C31 C41 136.4(3)
C28 C29 C31 C41 -47.1(4)
C30 C29 C31 C32 19.3(3)
C28 C29 C31 C32 -164.2(3)
C29 C31 C32 C33 -42.7(3)
C38 C31 C32 C33 77.6(3)
C41 C31 C32 C33 -164.0(2)
C30 O8 C33 C34 157.4(2)
C30 O8 C33 C32 -26.8(3)
C31 C32 C33 C34 -134.9(3)
C31 C32 C33 O8 49.6(3)
O8 C33 C34 C35 -6.4(4)
C32 C33 C34 C35 178.2(3)
C36 O10 C35 O9 -3.4(4)
C36 O10 C35 C34 176.1(2)
C33 C34 C35 O9 11.9(5)
C33 C34 C35 O10 -167.5(3)
C35 O10 C36 C37 178.3(3)
C39 O12 C38 O11 -0.3(4)
C39 O12 C38 C31 177.0(3)
C29 C31 C38 O11 108.0(3)
C41 C31 C38 O11 -128.2(3)
C32 C31 C38 O11 -11.1(3)
C29 C31 C38 O12 -69.3(3)
C41 C31 C38 O12 54.4(3)
C32 C31 C38 O12 171.5(2)
C38 O12 C39 C40 -178.7(3)
C42' O14 C41 O13 -25.2(6)
C42 O14 C41 O13 18.4(6)
C42' O14 C41 C31 152.5(4)
C42 O14 C41 C31 -163.9(4)
C29 C31 C41 O13 -12.2(5)
C38 C31 C41 O13 -133.9(3)
C32 C31 C41 O13 105.6(4)
C29 C31 C41 O14 170.1(3)
C38 C31 C41 O14 48.3(4)
C32 C31 C41 O14 -72.1(4)
C41 O14 C42 C43 -100.5(5)
C42' O14 C42 C43 -3.8(4)
C41 O14 C42' C43' 109.2(5)
C42 O14 C42' C43' 6.7(5)
|
1501986.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501986.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501986
loop_
_publ_author_name
'Akhigbe, Joshua'
'Zeller, Matthias'
'Br\"uckner, Christian'
_publ_section_title
;
Quinoline-annulated porphyrins.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1322
_journal_page_last 1325
_journal_paper_doi 10.1021/ol1031848
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C44 H26 N6 O'
_chemical_formula_weight 654.71
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 97.710(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 25.595(6)
_cell_length_b 9.572(2)
_cell_length_c 25.369(6)
_cell_measurement_reflns_used 2479
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 20.9877
_cell_measurement_theta_min 2.2800
_cell_volume 6159(2)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0729
_diffrn_reflns_av_sigmaI/netI 0.1229
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_number 36350
_diffrn_reflns_theta_full 28.28
_diffrn_reflns_theta_max 28.28
_diffrn_reflns_theta_min 0.80
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.087
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.6554
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Apex2 v2009.7-0 (Bruker, 2009)'
_exptl_crystal_colour black
_exptl_crystal_density_diffrn 1.412
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 2720
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.09
_refine_diff_density_max 0.320
_refine_diff_density_min -0.269
_refine_diff_density_rms 0.057
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 1017
_refine_ls_number_reflns 15006
_refine_ls_number_restraints 91
_refine_ls_restrained_S_all 1.021
_refine_ls_R_factor_all 0.1531
_refine_ls_R_factor_gt 0.0692
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.8186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1491
_refine_ls_wR_factor_ref 0.1786
_reflns_number_gt 7663
_reflns_number_total 15006
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol1031848_si_002.cif
_cod_data_source_block 10mz505_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P21/c
_cod_database_code 1501986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.10325(11) 0.2322(3) 0.49284(11) 0.0330(7) Uani 1 1 d . . .
C2A C 0.04821(11) 0.2202(4) 0.49671(11) 0.0386(8) Uani 1 1 d . . .
H2A H 0.0293 0.2704 0.5204 0.046 Uiso 1 1 calc R . .
C3A C 0.02779(11) 0.1234(3) 0.46027(11) 0.0353(7) Uani 1 1 d . . .
H3A H -0.0080 0.0945 0.4540 0.042 Uiso 1 1 calc R . .
C4A C 0.06920(10) 0.0729(3) 0.43310(10) 0.0319(7) Uani 1 1 d . . .
C5A C 0.06455(11) -0.0288(3) 0.39380(11) 0.0329(7) Uani 1 1 d . . .
C6A C 0.10738(11) -0.0904(3) 0.37158(11) 0.0356(7) Uani 1 1 d . . .
C7A C 0.10142(12) -0.1837(4) 0.32691(12) 0.0451(9) Uani 1 1 d . . .
H7A H 0.0691 -0.2160 0.3080 0.054 Uiso 1 1 calc R . .
C8A C 0.15022(12) -0.2168(4) 0.31672(12) 0.0430(8) Uani 1 1 d . . .
H8A H 0.1590 -0.2761 0.2892 0.052 Uiso 1 1 calc R . .
C9A C 0.18650(11) -0.1451(3) 0.35570(11) 0.0319(7) Uani 1 1 d . . .
C10A C 0.24162(11) -0.1589(3) 0.36025(11) 0.0288(6) Uani 1 1 d . . .
C11A C 0.27745(10) -0.1100(3) 0.40276(11) 0.0270(6) Uani 1 1 d . . .
C12A C 0.33337(10) -0.1239(3) 0.41046(11) 0.0299(7) Uani 1 1 d . . .
H12A H 0.3541 -0.1636 0.3859 0.036 Uiso 1 1 calc R . .
C13A C 0.35193(11) -0.0708(3) 0.45896(11) 0.0301(7) Uani 1 1 d . . .
H13A H 0.3878 -0.0681 0.4746 0.036 Uiso 1 1 calc R . .
C14A C 0.30806(10) -0.0199(3) 0.48210(11) 0.0271(6) Uani 1 1 d . . .
C15A C 0.30777(10) 0.0518(3) 0.53162(11) 0.0261(6) Uani 1 1 d . . .
C16A C 0.26794(10) 0.1440(3) 0.54118(10) 0.0261(6) Uani 1 1 d . . .
C17A C 0.27408(10) 0.2274(3) 0.58904(10) 0.0261(6) Uani 1 1 d . B .
C18A C 0.22683(10) 0.3100(3) 0.58538(11) 0.0268(6) Uani 1 1 d . B .
C19A C 0.19459(10) 0.2652(3) 0.53730(10) 0.0268(6) Uani 1 1 d . . .
C20A C 0.14197(11) 0.3084(3) 0.52721(10) 0.0307(7) Uani 1 1 d . . .
C21A C 0.01017(11) -0.0767(3) 0.37325(11) 0.0341(7) Uani 1 1 d . . .
C22A C -0.02797(11) 0.0197(4) 0.35228(11) 0.0373(8) Uani 1 1 d . . .
H22A H -0.0192 0.1161 0.3515 0.045 Uiso 1 1 calc R . .
C23A C -0.07878(12) -0.0241(4) 0.33242(12) 0.0454(9) Uani 1 1 d . . .
H23A H -0.1044 0.0420 0.3178 0.055 Uiso 1 1 calc R . .
C24A C -0.09162(12) -0.1635(4) 0.33417(13) 0.0487(9) Uani 1 1 d . . .
H24A H -0.1263 -0.1936 0.3212 0.058 Uiso 1 1 calc R . .
C25A C -0.05430(12) -0.2592(4) 0.35462(12) 0.0425(8) Uani 1 1 d . . .
H25A H -0.0634 -0.3554 0.3555 0.051 Uiso 1 1 calc R . .
C26A C -0.00348(12) -0.2169(4) 0.37408(11) 0.0387(8) Uani 1 1 d . . .
H26A H 0.0220 -0.2841 0.3880 0.046 Uiso 1 1 calc R . .
C27A C 0.26335(10) -0.2361(3) 0.31691(11) 0.0297(7) Uani 1 1 d . . .
C28A C 0.25520(11) -0.1826(3) 0.26511(11) 0.0345(7) Uani 1 1 d . . .
H28A H 0.2363 -0.0977 0.2582 0.041 Uiso 1 1 calc R . .
C29A C 0.27430(12) -0.2520(3) 0.22406(13) 0.0411(8) Uani 1 1 d . . .
H29A H 0.2691 -0.2142 0.1891 0.049 Uiso 1 1 calc R . .
C30A C 0.30093(13) -0.3759(4) 0.23378(15) 0.0512(9) Uani 1 1 d . . .
H30A H 0.3138 -0.4241 0.2054 0.061 Uiso 1 1 calc R . .
C31A C 0.30922(12) -0.4313(4) 0.28465(15) 0.0475(9) Uani 1 1 d . . .
H31A H 0.3277 -0.5170 0.2911 0.057 Uiso 1 1 calc R . .
C32A C 0.29044(11) -0.3610(3) 0.32618(13) 0.0371(7) Uani 1 1 d . . .
H32A H 0.2962 -0.3987 0.3611 0.045 Uiso 1 1 calc R . .
C33A C 0.34781(10) 0.0277(3) 0.57708(11) 0.0275(6) Uani 1 1 d . . .
C34A C 0.38242(11) -0.0889(3) 0.58066(12) 0.0337(7) Uani 1 1 d . . .
H34A H 0.3810 -0.1519 0.5516 0.040 Uiso 1 1 calc R . .
C35A C 0.41817(11) -0.1123(3) 0.62557(12) 0.0385(8) Uani 1 1 d . . .
H35A H 0.4404 -0.1922 0.6274 0.046 Uiso 1 1 calc R . .
C36A C 0.42183(11) -0.0190(4) 0.66847(13) 0.0401(8) Uani 1 1 d . . .
H36A H 0.4479 -0.0327 0.6984 0.048 Uiso 1 1 calc R . .
C37A C 0.38812(11) 0.0913(3) 0.66720(12) 0.0367(7) Uani 1 1 d . . .
H37A H 0.3904 0.1535 0.6966 0.044 Uiso 1 1 calc R . .
C38A C 0.34998(11) 0.1140(3) 0.62271(11) 0.0307(7) Uani 1 1 d . B .
C39A C 0.12688(11) 0.4200(3) 0.56077(11) 0.0343(7) Uani 1 1 d . . .
C40A C 0.16099(11) 0.4619(3) 0.60661(11) 0.0324(7) Uani 1 1 d . B .
C41A C 0.14624(12) 0.5641(3) 0.64151(12) 0.0390(8) Uani 1 1 d . . .
H41A H 0.1695 0.5886 0.6725 0.047 Uiso 1 1 calc R . .
C42A C 0.09843(13) 0.6278(4) 0.63075(13) 0.0466(8) Uani 1 1 d . . .
H42A H 0.0877 0.6941 0.6550 0.056 Uiso 1 1 calc R . .
C43A C 0.06546(14) 0.5956(4) 0.58440(13) 0.0495(9) Uani 1 1 d . . .
H43A H 0.0327 0.6429 0.5764 0.059 Uiso 1 1 calc R . .
C44A C 0.07965(12) 0.4963(4) 0.55003(12) 0.0424(8) Uani 1 1 d . . .
H44A H 0.0569 0.4785 0.5180 0.051 Uiso 1 1 calc R . .
C5C C 0.36761(11) 0.1756(3) 0.33999(10) 0.0285(6) Uani 1 1 d D . .
C6C C 0.39483(10) 0.2031(3) 0.39096(10) 0.0238(6) Uani 1 1 d . A .
C7C C 0.44790(10) 0.1585(3) 0.40883(10) 0.0261(6) Uani 1 1 d . . .
H7C H 0.4702 0.1076 0.3887 0.031 Uiso 1 1 calc R A .
C8C C 0.45990(10) 0.2022(3) 0.45932(10) 0.0243(6) Uani 1 1 d . A .
H8C H 0.4921 0.1874 0.4819 0.029 Uiso 1 1 calc R . .
C9C C 0.41411(10) 0.2764(3) 0.47245(10) 0.0240(6) Uani 1 1 d . . .
C10C C 0.41255(10) 0.3486(3) 0.52065(10) 0.0235(6) Uani 1 1 d . A .
C11C C 0.37142(10) 0.4302(3) 0.53423(11) 0.0262(6) Uani 1 1 d . . .
C12C C 0.36787(11) 0.4892(3) 0.58501(11) 0.0289(6) Uani 1 1 d . A .
H12C H 0.3935 0.4800 0.6156 0.035 Uiso 1 1 calc R . .
C13C C 0.32169(11) 0.5611(3) 0.58254(12) 0.0320(7) Uani 1 1 d . . .
H13C H 0.3094 0.6098 0.6111 0.038 Uiso 1 1 calc R A .
C14C C 0.29500(11) 0.5508(3) 0.52971(12) 0.0335(7) Uani 1 1 d D A .
C21C C 0.39797(11) 0.1164(3) 0.29882(10) 0.0304(7) Uani 1 1 d . A .
C22C C 0.38441(12) -0.0121(3) 0.27511(11) 0.0350(7) Uani 1 1 d . . .
H22C H 0.3561 -0.0643 0.2860 0.042 Uiso 1 1 calc R A .
C23C C 0.41166(12) -0.0646(4) 0.23598(12) 0.0432(8) Uani 1 1 d . A .
H23C H 0.4023 -0.1527 0.2203 0.052 Uiso 1 1 calc R . .
C24C C 0.45273(13) 0.0114(4) 0.21959(12) 0.0464(9) Uani 1 1 d . . .
H24C H 0.4714 -0.0246 0.1926 0.056 Uiso 1 1 calc R A .
C25C C 0.46652(12) 0.1404(4) 0.24275(12) 0.0412(8) Uani 1 1 d . A .
H25C H 0.4943 0.1934 0.2312 0.049 Uiso 1 1 calc R . .
C26C C 0.43989(11) 0.1912(3) 0.28243(11) 0.0349(7) Uani 1 1 d . . .
H26C H 0.4501 0.2780 0.2988 0.042 Uiso 1 1 calc R A .
C27C C 0.46106(10) 0.3431(3) 0.56113(10) 0.0230(6) Uani 1 1 d . . .
C28C C 0.47718(10) 0.2190(3) 0.58769(10) 0.0264(6) Uani 1 1 d . A .
H28C H 0.4572 0.1360 0.5803 0.032 Uiso 1 1 calc R . .
C29C C 0.52215(11) 0.2170(3) 0.62464(11) 0.0300(7) Uani 1 1 d . . .
H29C H 0.5322 0.1331 0.6433 0.036 Uiso 1 1 calc R A .
C30C C 0.55256(11) 0.3359(3) 0.63459(11) 0.0292(7) Uani 1 1 d . A .
H30C H 0.5836 0.3333 0.6597 0.035 Uiso 1 1 calc R . .
C31C C 0.53768(11) 0.4581(3) 0.60803(11) 0.0319(7) Uani 1 1 d . . .
H31C H 0.5587 0.5398 0.6145 0.038 Uiso 1 1 calc R A .
C32C C 0.49149(11) 0.4617(3) 0.57140(11) 0.0290(7) Uani 1 1 d . A .
H32C H 0.4810 0.5464 0.5535 0.035 Uiso 1 1 calc R . .
O1C O 0.08962(14) 0.7150(5) 0.46321(14) 0.0451(12) Uani 0.522(3) 1 d P A 1
C1C C 0.2279(6) 0.271(3) 0.3351(8) 0.025(2) Uani 0.522(3) 1 d PD A 1
C2C C 0.2331(7) 0.229(3) 0.2822(8) 0.030(3) Uani 0.522(3) 1 d PD A 1
H2C H 0.2052 0.2279 0.2535 0.036 Uiso 0.522(3) 1 calc PR A 1
C3C C 0.2837(7) 0.193(3) 0.2788(6) 0.0264(19) Uani 0.522(3) 1 d PD A 1
H3C H 0.2970 0.1621 0.2476 0.032 Uiso 0.522(3) 1 calc PR A 1
C4C C 0.3134(4) 0.209(3) 0.3300(5) 0.019(2) Uani 0.522(3) 1 d PDU A 1
N1C N 0.2775(7) 0.260(3) 0.3616(8) 0.023(2) Uani 0.522(3) 1 d PD A 1
H1C H 0.2860 0.2832 0.3953 0.028 Uiso 0.522(3) 1 calc PR A 1
C15C C 0.2465(6) 0.6196(18) 0.5109(8) 0.026(2) Uani 0.522(3) 1 d PD A 1
C16C C 0.2179(6) 0.5595(18) 0.4661(6) 0.025(2) Uani 0.522(3) 1 d PDU A 1
C17C C 0.1630(6) 0.596(2) 0.4509(9) 0.033(2) Uani 0.522(3) 1 d PD A 1
C18C C 0.1445(4) 0.5094(11) 0.4067(6) 0.032(2) Uani 0.522(3) 1 d PDU A 1
C19C C 0.1899(5) 0.4230(16) 0.3995(5) 0.0242(18) Uani 0.522(3) 1 d PD A 1
C20C C 0.1838(4) 0.3285(13) 0.3574(4) 0.0240(17) Uani 0.522(3) 1 d PDU A 1
N4C N 0.2343(6) 0.4582(18) 0.4335(6) 0.025(2) Uani 0.522(3) 1 d PDU A 1
C33C C 0.2217(4) 0.7299(12) 0.5382(5) 0.0231(18) Uani 0.522(3) 1 d PD A 1
C34C C 0.2461(4) 0.8087(14) 0.5814(5) 0.0240(19) Uani 0.522(3) 1 d PD A 1
H34C H 0.2816 0.7885 0.5954 0.029 Uiso 0.522(3) 1 calc PR A 1
C35C C 0.2202(4) 0.9142(12) 0.6044(4) 0.0349(18) Uani 0.522(3) 1 d PD A 1
H35C H 0.2379 0.9659 0.6333 0.042 Uiso 0.522(3) 1 calc PR A 1
C36C C 0.1683(4) 0.9447(14) 0.5851(4) 0.041(2) Uani 0.522(3) 1 d PD A 1
H36C H 0.1505 1.0165 0.6015 0.049 Uiso 0.522(3) 1 calc PR A 1
C37C C 0.1425(4) 0.8739(12) 0.5432(5) 0.038(2) Uani 0.522(3) 1 d PD A 1
H37C H 0.1072 0.8977 0.5296 0.046 Uiso 0.522(3) 1 calc PR A 1
C38C C 0.1684(4) 0.7648(12) 0.5201(5) 0.034(2) Uani 0.522(3) 1 d PD A 1
N5C N 0.1383(5) 0.6918(13) 0.4773(4) 0.036(2) Uani 0.522(3) 1 d PD A 1
N6C N 0.0974(4) 0.5021(9) 0.3810(4) 0.040(2) Uani 0.522(3) 1 d PD A 1
C39C C 0.1301(3) 0.3100(9) 0.3297(4) 0.0304(17) Uani 0.522(3) 1 d PD A 1
C40C C 0.0896(3) 0.4006(9) 0.3422(4) 0.0341(17) Uani 0.522(3) 1 d PD A 1
C41C C 0.0382(3) 0.3866(9) 0.3159(3) 0.045(2) Uani 0.522(3) 1 d PD A 1
H41C H 0.0118 0.4516 0.3225 0.054 Uiso 0.522(3) 1 calc PR A 1
C42C C 0.0259(3) 0.2809(10) 0.2809(3) 0.0441(18) Uani 0.522(3) 1 d PD A 1
H42C H -0.0086 0.2753 0.2619 0.053 Uiso 0.522(3) 1 calc PR A 1
C43C C 0.0634(3) 0.1799(8) 0.2721(3) 0.0363(14) Uani 0.522(3) 1 d PD A 1
H43C H 0.0535 0.1019 0.2498 0.044 Uiso 0.522(3) 1 calc PR A 1
C44C C 0.1150(3) 0.1949(10) 0.2964(4) 0.0355(19) Uani 0.522(3) 1 d PD A 1
H44C H 0.1406 0.1267 0.2906 0.043 Uiso 0.522(3) 1 calc PR A 1
O1D O 0.0544(2) 0.5065(6) 0.3788(2) 0.0685(18) Uani 0.478(3) 1 d P A 2
C1D C 0.2316(6) 0.243(3) 0.3247(10) 0.025(2) Uani 0.478(3) 1 d PD A 2
C2D C 0.2344(7) 0.204(4) 0.2714(9) 0.030(3) Uani 0.478(3) 1 d PD A 2
H2D H 0.2056 0.1994 0.2436 0.036 Uiso 0.478(3) 1 calc PR A 2
C3D C 0.2855(8) 0.174(3) 0.2668(6) 0.0264(19) Uani 0.478(3) 1 d PD A 2
H3D H 0.2989 0.1449 0.2353 0.032 Uiso 0.478(3) 1 calc PR A 2
C4D C 0.3153(5) 0.193(3) 0.3178(6) 0.019(2) Uani 0.478(3) 1 d PD A 2
N1D N 0.2807(8) 0.236(4) 0.3523(9) 0.023(2) Uani 0.478(3) 1 d PD A 2
H1D H 0.2892 0.2564 0.3863 0.028 Uiso 0.478(3) 1 calc PR A 2
C15D C 0.2427(6) 0.585(2) 0.5026(9) 0.026(2) Uani 0.478(3) 1 d PD A 2
C16D C 0.2161(6) 0.528(2) 0.4551(7) 0.025(2) Uani 0.478(3) 1 d PD A 2
C17D C 0.1607(7) 0.558(3) 0.4400(10) 0.033(2) Uani 0.478(3) 1 d PD A 2
C18D C 0.1427(5) 0.4604(12) 0.3991(6) 0.032(2) Uani 0.478(3) 1 d PD A 2
C19D C 0.1893(6) 0.3865(17) 0.3869(6) 0.0242(18) Uani 0.478(3) 1 d PD A 2
C20D C 0.1867(4) 0.2954(14) 0.3441(4) 0.0240(17) Uani 0.478(3) 1 d PD A 2
N4D N 0.2319(7) 0.429(2) 0.4223(7) 0.025(2) Uani 0.478(3) 1 d PD A 2
C33D C 0.2125(4) 0.6963(13) 0.5249(6) 0.0231(18) Uani 0.478(3) 1 d PD A 2
C34D C 0.2345(5) 0.7882(15) 0.5648(5) 0.0240(19) Uani 0.478(3) 1 d PD A 2
H34D H 0.2709 0.7791 0.5776 0.029 Uiso 0.478(3) 1 calc PR A 2
C35D C 0.2064(4) 0.8907(13) 0.5865(5) 0.0349(18) Uani 0.478(3) 1 d PD A 2
H35D H 0.2230 0.9452 0.6152 0.042 Uiso 0.478(3) 1 calc PR A 2
C36D C 0.1540(5) 0.9152(15) 0.5668(5) 0.041(2) Uani 0.478(3) 1 d PD A 2
H36D H 0.1347 0.9874 0.5812 0.049 Uiso 0.478(3) 1 calc PR A 2
C37D C 0.1307(5) 0.8330(14) 0.5261(5) 0.038(2) Uani 0.478(3) 1 d PD A 2
H37D H 0.0947 0.8481 0.5124 0.046 Uiso 0.478(3) 1 calc PR A 2
C38D C 0.1590(4) 0.7265(14) 0.5043(6) 0.034(2) Uani 0.478(3) 1 d PD A 2
N5D N 0.1326(6) 0.6508(14) 0.4619(5) 0.036(2) Uani 0.478(3) 1 d PD A 2
N6D N 0.0952(5) 0.4403(11) 0.3706(5) 0.040(2) Uani 0.478(3) 1 d PD A 2
C39D C 0.1337(4) 0.2538(10) 0.3214(5) 0.0304(17) Uani 0.478(3) 1 d PD A 2
C40D C 0.0896(4) 0.3345(9) 0.3321(4) 0.0341(17) Uani 0.478(3) 1 d PD A 2
C41D C 0.0390(3) 0.3082(11) 0.3065(4) 0.045(2) Uani 0.478(3) 1 d PD A 2
H41D H 0.0104 0.3664 0.3127 0.054 Uiso 0.478(3) 1 calc PR A 2
C42D C 0.0308(3) 0.1978(10) 0.2722(3) 0.0441(18) Uani 0.478(3) 1 d PD A 2
H42D H -0.0035 0.1799 0.2542 0.053 Uiso 0.478(3) 1 calc PR A 2
C43D C 0.0728(3) 0.1107(9) 0.2633(3) 0.0363(14) Uani 0.478(3) 1 d PD A 2
H43D H 0.0666 0.0316 0.2407 0.044 Uiso 0.478(3) 1 calc PR A 2
C44D C 0.1234(4) 0.1404(12) 0.2874(5) 0.0355(19) Uani 0.478(3) 1 d PD A 2
H44D H 0.1518 0.0819 0.2806 0.043 Uiso 0.478(3) 1 calc PR A 2
N1A N 0.11456(9) 0.1415(3) 0.45458(9) 0.0302(6) Uani 1 1 d . . .
H1A H 0.1460 0.1285 0.4450 0.036 Uiso 1 1 calc R . .
N2A N 0.15934(9) -0.0676(3) 0.38886(9) 0.0302(6) Uani 1 1 d . . .
N3A N 0.26419(8) -0.0420(2) 0.44724(8) 0.0265(5) Uani 1 1 d . . .
H3A1 H 0.2321 -0.0171 0.4521 0.032 Uiso 1 1 calc R . .
N4A N 0.22035(9) 0.1691(2) 0.51075(9) 0.0279(5) Uani 1 1 d . . .
N5A N 0.31326(9) 0.2188(3) 0.62779(10) 0.0298(6) Uani 1 1 d . . .
N6A N 0.21107(9) 0.4003(2) 0.61966(9) 0.0290(5) Uani 1 1 d . . .
N2C N 0.37445(8) 0.2751(2) 0.43030(8) 0.0254(5) Uani 1 1 d . A .
N3C N 0.32560(9) 0.4682(2) 0.50211(9) 0.0296(5) Uani 1 1 d . A .
H3C1 H 0.3173 0.4429 0.4687 0.035 Uiso 1 1 calc R . .
O1A O 0.3238(3) 0.2900(10) 0.6661(3) 0.051(3) Uani 0.268(5) 1 d P B 1
O1B O 0.23859(10) 0.4376(3) 0.66256(10) 0.0348(9) Uani 0.732(5) 1 d P B 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.0264(16) 0.0407(18) 0.0304(16) -0.0010(13) -0.0013(13) 0.0081(14)
C2A 0.0264(16) 0.061(2) 0.0271(16) -0.0088(15) -0.0003(13) 0.0083(15)
C3A 0.0215(15) 0.057(2) 0.0253(15) -0.0052(14) -0.0035(12) 0.0050(14)
C4A 0.0172(14) 0.054(2) 0.0236(15) -0.0015(13) -0.0021(12) 0.0026(14)
C5A 0.0217(15) 0.050(2) 0.0262(15) -0.0044(13) 0.0007(12) 0.0032(14)
C6A 0.0228(16) 0.055(2) 0.0290(16) -0.0057(14) 0.0018(13) 0.0003(14)
C7A 0.0208(16) 0.074(3) 0.0391(18) -0.0226(17) -0.0011(14) -0.0018(16)
C8A 0.0289(17) 0.063(2) 0.0367(18) -0.0218(16) 0.0026(14) 0.0024(16)
C9A 0.0213(15) 0.0439(19) 0.0304(16) -0.0039(13) 0.0028(12) 0.0015(13)
C10A 0.0229(15) 0.0303(16) 0.0330(16) 0.0004(12) 0.0036(12) 0.0033(12)
C11A 0.0204(15) 0.0306(16) 0.0307(15) 0.0024(12) 0.0054(12) 0.0025(12)
C12A 0.0192(15) 0.0319(17) 0.0398(17) -0.0002(13) 0.0077(13) -0.0004(12)
C13A 0.0187(15) 0.0304(17) 0.0406(17) 0.0043(13) 0.0023(13) -0.0033(12)
C14A 0.0196(15) 0.0279(16) 0.0328(16) 0.0071(12) 0.0005(12) -0.0015(12)
C15A 0.0185(14) 0.0261(15) 0.0326(15) 0.0072(12) -0.0003(12) -0.0040(12)
C16A 0.0207(14) 0.0310(16) 0.0253(14) 0.0054(12) -0.0017(12) -0.0033(12)
C17A 0.0237(15) 0.0281(16) 0.0256(15) 0.0032(12) 0.0000(12) -0.0064(12)
C18A 0.0207(14) 0.0317(16) 0.0275(15) 0.0030(12) 0.0018(12) -0.0040(12)
C19A 0.0239(15) 0.0302(16) 0.0262(15) 0.0016(12) 0.0032(12) -0.0011(12)
C20A 0.0254(16) 0.0413(18) 0.0244(15) 0.0001(13) -0.0006(12) 0.0039(13)
C21A 0.0200(15) 0.055(2) 0.0267(15) -0.0118(14) 0.0033(12) 0.0026(14)
C22A 0.0235(16) 0.058(2) 0.0295(16) -0.0164(15) -0.0001(13) 0.0046(15)
C23A 0.0245(17) 0.068(3) 0.0419(19) -0.0241(17) -0.0032(14) 0.0122(17)
C24A 0.0196(16) 0.077(3) 0.048(2) -0.0317(19) 0.0004(14) 0.0019(17)
C25A 0.0284(17) 0.061(2) 0.0385(18) -0.0204(16) 0.0063(14) -0.0045(16)
C26A 0.0282(17) 0.055(2) 0.0331(17) -0.0078(15) 0.0046(13) 0.0007(16)
C27A 0.0195(14) 0.0321(17) 0.0380(17) -0.0063(13) 0.0057(12) 0.0004(13)
C28A 0.0277(16) 0.0386(19) 0.0373(17) -0.0077(14) 0.0042(13) 0.0051(14)
C29A 0.0397(19) 0.044(2) 0.0416(18) -0.0087(15) 0.0119(15) -0.0014(16)
C30A 0.041(2) 0.056(2) 0.059(2) -0.0232(19) 0.0158(18) 0.0067(18)
C31A 0.0357(19) 0.035(2) 0.072(3) -0.0142(17) 0.0106(17) 0.0076(15)
C32A 0.0299(17) 0.0313(18) 0.0509(19) 0.0013(14) 0.0077(14) -0.0010(14)
C33A 0.0184(14) 0.0294(16) 0.0336(16) 0.0076(12) -0.0012(12) -0.0075(12)
C34A 0.0214(15) 0.0353(18) 0.0434(18) 0.0097(14) 0.0007(13) -0.0038(13)
C35A 0.0209(16) 0.0379(19) 0.054(2) 0.0213(16) -0.0030(14) -0.0040(14)
C36A 0.0238(16) 0.050(2) 0.0429(19) 0.0215(16) -0.0093(14) -0.0110(15)
C37A 0.0270(16) 0.046(2) 0.0342(17) 0.0094(14) -0.0055(13) -0.0122(15)
C38A 0.0270(16) 0.0330(17) 0.0301(16) 0.0104(13) -0.0040(13) -0.0123(13)
C39A 0.0296(17) 0.0435(19) 0.0299(16) 0.0003(13) 0.0039(13) 0.0015(14)
C40A 0.0284(16) 0.0371(18) 0.0321(16) 0.0000(13) 0.0056(13) -0.0012(14)
C41A 0.0385(19) 0.041(2) 0.0379(18) -0.0074(14) 0.0069(14) -0.0027(15)
C42A 0.045(2) 0.046(2) 0.050(2) -0.0104(16) 0.0104(17) 0.0035(17)
C43A 0.044(2) 0.056(2) 0.049(2) -0.0027(17) 0.0083(17) 0.0152(18)
C44A 0.0374(19) 0.050(2) 0.0381(18) -0.0048(15) 0.0002(15) 0.0123(16)
C5C 0.0270(16) 0.0291(16) 0.0286(15) 0.0056(12) 0.0006(12) -0.0018(13)
C6C 0.0216(14) 0.0234(15) 0.0256(14) 0.0060(11) -0.0001(12) -0.0006(12)
C7C 0.0195(14) 0.0280(16) 0.0306(15) 0.0044(12) 0.0029(12) -0.0014(12)
C8C 0.0170(14) 0.0254(15) 0.0288(15) 0.0035(11) -0.0025(11) 0.0002(11)
C9C 0.0184(14) 0.0267(15) 0.0262(14) 0.0058(11) 0.0008(11) 0.0006(12)
C10C 0.0207(14) 0.0206(14) 0.0288(15) 0.0067(11) 0.0014(11) -0.0032(11)
C11C 0.0229(15) 0.0231(15) 0.0329(15) 0.0041(12) 0.0046(12) -0.0014(12)
C12C 0.0281(16) 0.0213(15) 0.0374(16) 0.0013(12) 0.0048(13) -0.0033(12)
C13C 0.0303(17) 0.0265(16) 0.0419(18) 0.0039(13) 0.0141(14) 0.0011(13)
C14C 0.0260(16) 0.0283(17) 0.0492(19) 0.0140(14) 0.0158(14) 0.0062(13)
C21C 0.0276(16) 0.0372(18) 0.0242(15) 0.0063(13) -0.0047(12) 0.0017(13)
C22C 0.0310(17) 0.044(2) 0.0281(16) 0.0005(14) -0.0011(13) 0.0006(14)
C23C 0.041(2) 0.049(2) 0.0368(18) -0.0045(15) -0.0054(15) 0.0078(17)
C24C 0.0358(19) 0.074(3) 0.0282(17) 0.0070(17) 0.0006(14) 0.0159(18)
C25C 0.0282(17) 0.061(2) 0.0342(17) 0.0148(16) 0.0025(14) 0.0047(16)
C26C 0.0303(17) 0.046(2) 0.0264(15) 0.0111(13) -0.0031(13) 0.0012(14)
C27C 0.0186(14) 0.0267(15) 0.0241(14) 0.0023(11) 0.0047(11) 0.0014(11)
C28C 0.0237(15) 0.0227(15) 0.0315(15) 0.0004(12) -0.0013(12) -0.0038(12)
C29C 0.0292(16) 0.0239(16) 0.0345(16) 0.0023(12) -0.0041(13) 0.0024(13)
C30C 0.0182(14) 0.0407(18) 0.0276(15) -0.0029(13) -0.0014(12) 0.0024(13)
C31C 0.0280(16) 0.0299(17) 0.0376(17) 0.0017(13) 0.0034(13) -0.0082(13)
C32C 0.0310(16) 0.0247(16) 0.0312(16) 0.0031(12) 0.0038(13) -0.0056(13)
O1C 0.018(2) 0.082(3) 0.034(2) 0.008(2) -0.0004(17) 0.028(2)
C1C 0.025(2) 0.033(9) 0.017(7) -0.003(4) 0.000(3) 0.002(3)
C2C 0.0289(19) 0.036(10) 0.021(7) -0.001(5) -0.010(3) -0.003(3)
C3C 0.032(2) 0.036(7) 0.010(6) -0.008(5) -0.002(3) 0.000(2)
C4C 0.0281(17) 0.027(5) 0.003(6) -0.004(5) 0.002(2) -0.0009(16)
N1C 0.022(2) 0.034(9) 0.014(6) -0.006(4) 0.000(3) 0.004(3)
C15C 0.029(2) 0.009(8) 0.044(6) 0.005(3) 0.015(2) 0.004(4)
C16C 0.0283(19) 0.028(7) 0.020(6) 0.003(3) 0.011(3) 0.012(3)
C17C 0.030(2) 0.047(11) 0.025(8) 0.004(4) 0.010(3) 0.019(4)
C18C 0.0217(19) 0.041(7) 0.033(4) 0.011(4) 0.003(2) 0.007(4)
C19C 0.0217(17) 0.041(7) 0.010(6) -0.006(3) 0.002(3) 0.006(4)
C20C 0.0198(18) 0.048(6) 0.004(5) -0.007(3) 0.003(3) 0.006(3)
N4C 0.0231(18) 0.037(6) 0.015(6) 0.001(4) 0.000(3) 0.005(3)
C33C 0.028(4) 0.014(5) 0.029(7) -0.004(3) 0.006(3) -0.003(3)
C34C 0.029(5) 0.019(4) 0.025(7) 0.002(3) 0.005(4) 0.003(4)
C35C 0.046(5) 0.029(4) 0.033(6) 0.003(3) 0.018(4) -0.003(4)
C36C 0.049(6) 0.041(6) 0.035(7) 0.008(4) 0.015(4) 0.017(5)
C37C 0.030(5) 0.045(7) 0.041(7) 0.009(4) 0.013(4) 0.012(4)
C38C 0.037(4) 0.035(6) 0.031(7) 0.003(3) 0.012(4) 0.009(4)
N5C 0.039(3) 0.048(7) 0.022(6) 0.002(3) 0.013(4) 0.026(4)
N6C 0.0190(19) 0.065(7) 0.038(4) 0.006(4) 0.004(2) 0.014(5)
C39C 0.023(2) 0.039(6) 0.029(4) 0.007(4) 0.000(2) 0.005(4)
C40C 0.025(2) 0.045(6) 0.031(4) 0.010(4) -0.001(2) 0.006(4)
C41C 0.022(2) 0.079(7) 0.033(3) 0.004(4) -0.002(2) 0.011(4)
C42C 0.021(2) 0.072(6) 0.037(3) 0.013(4) -0.003(2) 0.004(4)
C43C 0.029(3) 0.050(5) 0.029(3) 0.001(3) 0.001(2) 0.000(4)
C44C 0.024(3) 0.054(7) 0.028(4) 0.010(4) 0.001(3) 0.002(3)
O1D 0.047(4) 0.077(4) 0.083(4) -0.020(3) 0.010(3) 0.024(3)
C1D 0.025(2) 0.033(9) 0.017(7) -0.003(4) 0.000(3) 0.002(3)
C2D 0.0289(19) 0.036(10) 0.021(7) -0.001(5) -0.010(3) -0.003(3)
C3D 0.032(2) 0.036(7) 0.010(6) -0.008(5) -0.002(3) 0.000(2)
C4D 0.0281(17) 0.027(5) 0.003(6) -0.004(5) 0.002(2) -0.0009(16)
N1D 0.022(2) 0.034(9) 0.014(6) -0.006(4) 0.000(3) 0.004(3)
C15D 0.029(2) 0.009(8) 0.044(6) 0.005(3) 0.015(2) 0.004(4)
C16D 0.0283(19) 0.028(7) 0.020(6) 0.003(3) 0.011(3) 0.012(3)
C17D 0.030(2) 0.047(11) 0.025(8) 0.004(4) 0.010(3) 0.019(4)
C18D 0.0217(19) 0.041(7) 0.033(4) 0.011(4) 0.003(2) 0.007(4)
C19D 0.0217(17) 0.041(7) 0.010(6) -0.006(3) 0.002(3) 0.006(4)
C20D 0.0198(18) 0.048(6) 0.004(5) -0.007(3) 0.003(3) 0.006(3)
N4D 0.0231(18) 0.037(6) 0.015(6) 0.001(4) 0.000(3) 0.005(3)
C33D 0.028(4) 0.014(5) 0.029(7) -0.004(3) 0.006(3) -0.003(3)
C34D 0.029(5) 0.019(4) 0.025(7) 0.002(3) 0.005(4) 0.003(4)
C35D 0.046(5) 0.029(4) 0.033(6) 0.003(3) 0.018(4) -0.003(4)
C36D 0.049(6) 0.041(6) 0.035(7) 0.008(4) 0.015(4) 0.017(5)
C37D 0.030(5) 0.045(7) 0.041(7) 0.009(4) 0.013(4) 0.012(4)
C38D 0.037(4) 0.035(6) 0.031(7) 0.003(3) 0.012(4) 0.009(4)
N5D 0.039(3) 0.048(7) 0.022(6) 0.002(3) 0.013(4) 0.026(4)
N6D 0.0190(19) 0.065(7) 0.038(4) 0.006(4) 0.004(2) 0.014(5)
C39D 0.023(2) 0.039(6) 0.029(4) 0.007(4) 0.000(2) 0.005(4)
C40D 0.025(2) 0.045(6) 0.031(4) 0.010(4) -0.001(2) 0.006(4)
C41D 0.022(2) 0.079(7) 0.033(3) 0.004(4) -0.002(2) 0.011(4)
C42D 0.021(2) 0.072(6) 0.037(3) 0.013(4) -0.003(2) 0.004(4)
C43D 0.029(3) 0.050(5) 0.029(3) 0.001(3) 0.001(2) 0.000(4)
C44D 0.024(3) 0.054(7) 0.028(4) 0.010(4) 0.001(3) 0.002(3)
N1A 0.0188(12) 0.0423(15) 0.0290(13) -0.0029(11) 0.0009(10) 0.0054(11)
N2A 0.0194(13) 0.0423(15) 0.0296(13) -0.0009(11) 0.0062(10) 0.0024(11)
N3A 0.0167(12) 0.0313(14) 0.0313(13) -0.0014(10) 0.0032(10) 0.0018(10)
N4A 0.0227(13) 0.0315(14) 0.0289(13) 0.0031(10) 0.0008(10) 0.0021(10)
N5A 0.0239(13) 0.0316(14) 0.0319(14) 0.0049(11) -0.0038(11) -0.0063(11)
N6A 0.0281(13) 0.0337(14) 0.0249(13) -0.0004(10) 0.0027(11) -0.0079(11)
N2C 0.0201(12) 0.0265(13) 0.0289(12) 0.0055(10) 0.0007(10) 0.0017(10)
N3C 0.0246(13) 0.0307(14) 0.0337(13) 0.0089(10) 0.0049(10) 0.0061(11)
O1A 0.039(5) 0.071(7) 0.042(5) -0.011(5) -0.001(4) -0.015(5)
O1B 0.0311(17) 0.0421(18) 0.0288(16) -0.0039(12) -0.0044(12) -0.0031(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1A C1A C20A 124.3(2)
N1A C1A C2A 107.7(3)
C20A C1A C2A 127.4(3)
C3A C2A C1A 107.4(3)
C3A C2A H2A 126.3
C1A C2A H2A 126.3
C2A C3A C4A 108.5(3)
C2A C3A H3A 125.8
C4A C3A H3A 125.8
N1A C4A C5A 127.1(2)
N1A C4A C3A 106.8(2)
C5A C4A C3A 126.1(3)
C4A C5A C6A 125.3(3)
C4A C5A C21A 116.9(2)
C6A C5A C21A 117.7(3)
N2A C6A C5A 125.2(3)
N2A C6A C7A 110.5(2)
C5A C6A C7A 124.3(3)
C8A C7A C6A 107.2(3)
C8A C7A H7A 126.4
C6A C7A H7A 126.4
C7A C8A C9A 106.6(3)
C7A C8A H8A 126.7
C9A C8A H8A 126.7
N2A C9A C10A 125.7(3)
N2A C9A C8A 110.2(2)
C10A C9A C8A 124.1(3)
C11A C10A C9A 125.3(3)
C11A C10A C27A 117.6(2)
C9A C10A C27A 117.1(2)
N3A C11A C10A 125.4(2)
N3A C11A C12A 106.5(2)
C10A C11A C12A 128.1(3)
C13A C12A C11A 108.2(2)
C13A C12A H12A 125.9
C11A C12A H12A 125.9
C12A C13A C14A 107.7(2)
C12A C13A H13A 126.2
C14A C13A H13A 126.2
N3A C14A C13A 108.0(2)
N3A C14A C15A 123.3(2)
C13A C14A C15A 128.6(2)
C16A C15A C14A 123.1(2)
C16A C15A C33A 114.6(2)
C14A C15A C33A 122.2(2)
N4A C16A C15A 128.8(2)
N4A C16A C17A 111.4(2)
C15A C16A C17A 119.8(2)
N5A C17A C18A 129.5(3)
N5A C17A C16A 125.6(3)
C18A C17A C16A 104.7(2)
N6A C18A C17A 130.0(2)
N6A C18A C19A 123.9(2)
C17A C18A C19A 105.8(2)
N4A C19A C20A 128.8(3)
N4A C19A C18A 111.0(2)
C20A C19A C18A 119.6(2)
C19A C20A C1A 122.2(3)
C19A C20A C39A 115.8(2)
C1A C20A C39A 121.1(3)
C26A C21A C22A 118.7(3)
C26A C21A C5A 121.1(3)
C22A C21A C5A 120.1(3)
C23A C22A C21A 120.7(3)
C23A C22A H22A 119.7
C21A C22A H22A 119.7
C24A C23A C22A 119.6(3)
C24A C23A H23A 120.2
C22A C23A H23A 120.2
C25A C24A C23A 120.1(3)
C25A C24A H24A 119.9
C23A C24A H24A 119.9
C24A C25A C26A 120.7(3)
C24A C25A H25A 119.7
C26A C25A H25A 119.7
C21A C26A C25A 120.2(3)
C21A C26A H26A 119.9
C25A C26A H26A 119.9
C32A C27A C28A 118.9(3)
C32A C27A C10A 122.0(3)
C28A C27A C10A 119.1(3)
C29A C28A C27A 120.6(3)
C29A C28A H28A 119.7
C27A C28A H28A 119.7
C30A C29A C28A 119.9(3)
C30A C29A H29A 120.1
C28A C29A H29A 120.1
C29A C30A C31A 120.5(3)
C29A C30A H30A 119.7
C31A C30A H30A 119.7
C30A C31A C32A 119.7(3)
C30A C31A H31A 120.1
C32A C31A H31A 120.1
C27A C32A C31A 120.3(3)
C27A C32A H32A 119.8
C31A C32A H32A 119.8
C38A C33A C34A 116.7(3)
C38A C33A C15A 120.1(3)
C34A C33A C15A 122.9(3)
C35A C34A C33A 121.3(3)
C35A C34A H34A 119.4
C33A C34A H34A 119.4
C34A C35A C36A 120.3(3)
C34A C35A H35A 119.8
C36A C35A H35A 119.8
C37A C36A C35A 120.0(3)
C37A C36A H36A 120.0
C35A C36A H36A 120.0
C36A C37A C38A 120.5(3)
C36A C37A H37A 119.7
C38A C37A H37A 119.7
N5A C38A C37A 116.2(3)
N5A C38A C33A 122.9(2)
C37A C38A C33A 120.8(3)
C44A C39A C40A 115.5(3)
C44A C39A C20A 123.9(3)
C40A C39A C20A 120.5(3)
C41A C40A N6A 117.2(3)
C41A C40A C39A 121.8(3)
N6A C40A C39A 121.0(3)
C42A C41A C40A 119.7(3)
C42A C41A H41A 120.1
C40A C41A H41A 120.1
C41A C42A C43A 119.9(3)
C41A C42A H42A 120.0
C43A C42A H42A 120.0
C44A C43A C42A 120.7(3)
C44A C43A H43A 119.7
C42A C43A H43A 119.7
C43A C44A C39A 122.0(3)
C43A C44A H44A 119.0
C39A C44A H44A 119.0
C4D C5C C6C 132.8(6)
C6C C5C C4C 118.4(5)
C4D C5C C21C 109.0(6)
C6C C5C C21C 118.2(2)
C4C C5C C21C 123.4(5)
N2C C6C C5C 124.9(2)
N2C C6C C7C 110.8(2)
C5C C6C C7C 124.3(2)
C8C C7C C6C 107.1(2)
C8C C7C H7C 126.5
C6C C7C H7C 126.5
C7C C8C C9C 106.5(2)
C7C C8C H8C 126.8
C9C C8C H8C 126.8
N2C C9C C10C 125.2(2)
N2C C9C C8C 110.7(2)
C10C C9C C8C 123.9(2)
C11C C10C C9C 126.9(2)
C11C C10C C27C 115.7(2)
C9C C10C C27C 117.3(2)
N3C C11C C10C 127.7(2)
N3C C11C C12C 106.1(2)
C10C C11C C12C 126.2(3)
C13C C12C C11C 108.7(3)
C13C C12C H12C 125.7
C11C C12C H12C 125.7
C12C C13C C14C 108.2(3)
C12C C13C H13C 125.9
C14C C13C H13C 125.9
N3C C14C C13C 106.6(2)
N3C C14C C15C 128.8(7)
C13C C14C C15C 124.6(7)
N3C C14C C15D 116.2(7)
C13C C14C C15D 136.2(8)
C22C C21C C26C 118.7(3)
C22C C21C C5C 120.9(3)
C26C C21C C5C 120.3(3)
C23C C22C C21C 120.7(3)
C23C C22C H22C 119.7
C21C C22C H22C 119.7
C22C C23C C24C 120.1(3)
C22C C23C H23C 120.0
C24C C23C H23C 120.0
C23C C24C C25C 119.9(3)
C23C C24C H24C 120.1
C25C C24C H24C 120.1
C26C C25C C24C 119.9(3)
C26C C25C H25C 120.0
C24C C25C H25C 120.0
C25C C26C C21C 120.7(3)
C25C C26C H26C 119.6
C21C C26C H26C 119.6
C32C C27C C28C 118.9(2)
C32C C27C C10C 119.6(2)
C28C C27C C10C 121.5(2)
C29C C28C C27C 120.2(3)
C29C C28C H28C 119.9
C27C C28C H28C 119.9
C30C C29C C28C 120.6(3)
C30C C29C H29C 119.7
C28C C29C H29C 119.7
C31C C30C C29C 119.8(3)
C31C C30C H30C 120.1
C29C C30C H30C 120.1
C30C C31C C32C 119.8(3)
C30C C31C H31C 120.1
C32C C31C H31C 120.1
C27C C32C C31C 120.6(3)
C27C C32C H32C 119.7
C31C C32C H32C 119.7
N1C C1C C2C 104.4(10)
N1C C1C C20C 124.2(13)
C2C C1C C20C 131.0(16)
C3C C2C C1C 110.1(10)
C3C C2C H2C 125.0
C1C C2C H2C 125.0
C2C C3C C4C 108.1(9)
C2C C3C H3C 125.9
C4C C3C H3C 125.9
N1C C4C C5C 133.3(12)
N1C C4C C3C 104.6(9)
C5C C4C C3C 122.1(11)
C1C N1C C4C 112.7(10)
C1C N1C H1C 123.7
C4C N1C H1C 123.7
C16C C15C C14C 114.9(9)
C16C C15C C33C 118.3(8)
C14C C15C C33C 126.2(10)
N4C C16C C15C 127.7(11)
N4C C16C C17C 111.9(9)
C15C C16C C17C 120.3(10)
N5C C17C C18C 131.4(11)
N5C C17C C16C 122.3(10)
C18C C17C C16C 106.2(9)
N6C C18C C17C 128.2(10)
N6C C18C C19C 127.7(9)
C17C C18C C19C 104.0(8)
N4C C19C C20C 129.8(9)
N4C C19C C18C 112.8(8)
C20C C19C C18C 117.1(9)
C19C C20C C1C 122.6(11)
C19C C20C C39C 116.5(8)
C1C C20C C39C 119.8(9)
C19C N4C C16C 104.8(10)
C34C C33C C38C 115.5(7)
C34C C33C C15C 125.8(9)
C38C C33C C15C 118.7(7)
C35C C34C C33C 122.3(8)
C35C C34C H34C 118.8
C33C C34C H34C 118.8
C34C C35C C36C 119.9(7)
C34C C35C H35C 120.1
C36C C35C H35C 120.1
C37C C36C C35C 121.0(8)
C37C C36C H36C 119.5
C35C C36C H36C 119.5
C36C C37C C38C 119.4(8)
C36C C37C H37C 120.3
C38C C37C H37C 120.3
C37C C38C C33C 121.8(7)
C37C C38C N5C 116.4(9)
C33C C38C N5C 121.8(8)
O1C N5C C17C 119.2(8)
O1C N5C C38C 122.6(8)
C17C N5C C38C 118.2(11)
C18C N6C C40C 115.7(8)
C44C C39C C40C 117.5(7)
C44C C39C C20C 122.9(7)
C40C C39C C20C 119.0(7)
N6C C40C C41C 116.5(8)
N6C C40C C39C 123.4(8)
C41C C40C C39C 120.1(7)
C42C C41C C40C 120.3(7)
C42C C41C H41C 119.8
C40C C41C H41C 119.8
C41C C42C C43C 121.1(7)
C41C C42C H42C 119.5
C43C C42C H42C 119.5
C44C C43C C42C 119.3(7)
C44C C43C H43C 120.4
C42C C43C H43C 120.4
C43C C44C C39C 120.9(7)
C43C C44C H44C 119.5
C39C C44C H44C 119.5
N1D C1D C20D 125.4(16)
N1D C1D C2D 108.7(11)
C20D C1D C2D 125.4(18)
C3D C2D C1D 108.1(11)
C3D C2D H2D 126.0
C1D C2D H2D 126.0
C2D C3D C4D 107.4(10)
C2D C3D H3D 126.3
C4D C3D H3D 126.3
N1D C4D C5C 116.1(13)
N1D C4D C3D 107.7(10)
C5C C4D C3D 136.2(13)
C1D N1D C4D 108.2(12)
C1D N1D H1D 125.9
C4D N1D H1D 125.9
C16D C15D C14C 128.3(11)
C16D C15D C33D 113.1(9)
C14C C15D C33D 118.6(10)
N4D C16D C15D 130.2(12)
N4D C16D C17D 109.7(11)
C15D C16D C17D 119.4(12)
N5D C17D C18D 127.5(13)
N5D C17D C16D 126.6(12)
C18D C17D C16D 105.8(10)
N6D C18D C17D 131.8(11)
N6D C18D C19D 121.6(10)
C17D C18D C19D 106.2(9)
N4D C19D C20D 130.1(10)
N4D C19D C18D 108.6(9)
C20D C19D C18D 121.2(10)
C19D C20D C1D 123.1(12)
C19D C20D C39D 115.2(9)
C1D C20D C39D 121.7(11)
C16D N4D C19D 109.2(11)
C34D C33D C38D 114.2(8)
C34D C33D C15D 123.4(10)
C38D C33D C15D 122.2(8)
C35D C34D C33D 123.8(9)
C35D C34D H34D 118.1
C33D C34D H34D 118.1
C34D C35D C36D 120.6(8)
C34D C35D H35D 119.7
C36D C35D H35D 119.7
C37D C36D C35D 118.4(10)
C37D C36D H36D 120.8
C35D C36D H36D 120.8
C36D C37D C38D 121.2(10)
C36D C37D H37D 119.4
C38D C37D H37D 119.4
N5D C38D C37D 117.3(10)
N5D C38D C33D 121.2(10)
C37D C38D C33D 121.5(8)
C17D N5D C38D 116.3(13)
O1D N6D C18D 123.3(9)
O1D N6D C40D 117.9(10)
C18D N6D C40D 118.7(9)
C44D C39D C40D 117.0(8)
C44D C39D C20D 123.1(8)
C40D C39D C20D 119.8(8)
C41D C40D N6D 117.3(9)
C41D C40D C39D 121.6(8)
N6D C40D C39D 121.0(8)
C42D C41D C40D 119.3(8)
C42D C41D H41D 120.3
C40D C41D H41D 120.3
C41D C42D C43D 120.5(8)
C41D C42D H42D 119.7
C43D C42D H42D 119.7
C44D C43D C42D 119.9(7)
C44D C43D H43D 120.1
C42D C43D H43D 120.1
C43D C44D C39D 121.5(8)
C43D C44D H44D 119.3
C39D C44D H44D 119.3
C1A N1A C4A 109.7(2)
C1A N1A H1A 125.2
C4A N1A H1A 125.2
C6A N2A C9A 105.6(2)
C14A N3A C11A 109.6(2)
C14A N3A H3A1 125.2
C11A N3A H3A1 125.2
C19A N4A C16A 107.0(2)
O1A N5A C17A 130.1(5)
O1A N5A C38A 114.1(5)
C17A N5A C38A 115.8(2)
O1B N6A C18A 124.3(3)
O1B N6A C40A 117.9(2)
C18A N6A C40A 117.8(2)
C6C N2C C9C 105.0(2)
C14C N3C C11C 110.4(2)
C14C N3C H3C1 124.8
C11C N3C H3C1 124.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1A N1A 1.362(3)
C1A C20A 1.429(4)
C1A C2A 1.430(4)
C2A C3A 1.362(4)
C2A H2A 0.9500
C3A C4A 1.424(4)
C3A H3A 0.9500
C4A N1A 1.381(3)
C4A C5A 1.387(4)
C5A C6A 1.426(4)
C5A C21A 1.492(4)
C6A N2A 1.361(3)
C6A C7A 1.435(4)
C7A C8A 1.347(4)
C7A H7A 0.9500
C8A C9A 1.437(4)
C8A H8A 0.9500
C9A N2A 1.377(3)
C9A C10A 1.406(4)
C10A C11A 1.399(4)
C10A C27A 1.493(4)
C11A N3A 1.384(3)
C11A C12A 1.425(4)
C12A C13A 1.357(4)
C12A H12A 0.9500
C13A C14A 1.421(4)
C13A H13A 0.9500
C14A N3A 1.350(3)
C14A C15A 1.432(4)
C15A C16A 1.394(4)
C15A C33A 1.455(4)
C16A N4A 1.373(3)
C16A C17A 1.444(4)
C17A N5A 1.309(3)
C17A C18A 1.437(4)
C18A N6A 1.326(3)
C18A C19A 1.443(4)
C19A N4A 1.362(3)
C19A C20A 1.399(4)
C20A C39A 1.450(4)
C21A C26A 1.387(4)
C21A C22A 1.396(4)
C22A C23A 1.394(4)
C22A H22A 0.9500
C23A C24A 1.377(5)
C23A H23A 0.9500
C24A C25A 1.374(5)
C24A H24A 0.9500
C25A C26A 1.388(4)
C25A H25A 0.9500
C26A H26A 0.9500
C27A C32A 1.386(4)
C27A C28A 1.400(4)
C28A C29A 1.379(4)
C28A H28A 0.9500
C29A C30A 1.374(5)
C29A H29A 0.9500
C30A C31A 1.385(5)
C30A H30A 0.9500
C31A C32A 1.389(4)
C31A H31A 0.9500
C32A H32A 0.9500
C33A C38A 1.417(4)
C33A C34A 1.420(4)
C34A C35A 1.381(4)
C34A H34A 0.9500
C35A C36A 1.401(5)
C35A H35A 0.9500
C36A C37A 1.361(4)
C36A H36A 0.9500
C37A C38A 1.407(4)
C37A H37A 0.9500
C38A N5A 1.392(4)
C39A C44A 1.408(4)
C39A C40A 1.415(4)
C40A C41A 1.404(4)
C40A N6A 1.410(4)
C41A C42A 1.362(4)
C41A H41A 0.9500
C42A C43A 1.387(5)
C42A H42A 0.9500
C43A C44A 1.371(4)
C43A H43A 0.9500
C44A H44A 0.9500
C5C C4D 1.391(10)
C5C C6C 1.409(4)
C5C C4C 1.413(9)
C5C C21C 1.495(4)
C6C N2C 1.372(3)
C6C C7C 1.438(4)
C7C C8C 1.343(4)
C7C H7C 0.9500
C8C C9C 1.447(4)
C8C H8C 0.9500
C9C N2C 1.372(3)
C9C C10C 1.410(4)
C10C C11C 1.391(4)
C10C C27C 1.502(4)
C11C N3C 1.384(3)
C11C C12C 1.420(4)
C12C C13C 1.362(4)
C12C H12C 0.9500
C13C C14C 1.424(4)
C13C H13C 0.9500
C14C N3C 1.369(3)
C14C C15C 1.430(9)
C14C C15D 1.460(10)
C21C C22C 1.393(4)
C21C C26C 1.399(4)
C22C C23C 1.382(4)
C22C H22C 0.9500
C23C C24C 1.387(5)
C23C H23C 0.9500
C24C C25C 1.393(5)
C24C H24C 0.9500
C25C C26C 1.378(4)
C25C H25C 0.9500
C26C H26C 0.9500
C27C C32C 1.382(4)
C27C C28C 1.400(4)
C28C C29C 1.384(4)
C28C H28C 0.9500
C29C C30C 1.383(4)
C29C H29C 0.9500
C30C C31C 1.378(4)
C30C H30C 0.9500
C31C C32C 1.403(4)
C31C H31C 0.9500
C32C H32C 0.9500
O1C N5C 1.268(14)
C1C N1C 1.359(10)
C1C C2C 1.421(10)
C1C C20C 1.440(9)
C2C C3C 1.356(10)
C2C H2C 0.9500
C3C C4C 1.422(10)
C3C H3C 0.9500
C4C N1C 1.389(9)
N1C H1C 0.8800
C15C C16C 1.393(9)
C15C C33C 1.453(10)
C16C N4C 1.376(13)
C16C C17C 1.447(10)
C17C N5C 1.347(11)
C17C C18C 1.420(9)
C18C N6C 1.294(13)
C18C C19C 1.458(10)
C19C N4C 1.373(15)
C19C C20C 1.392(8)
C20C C39C 1.470(9)
C33C C34C 1.407(8)
C33C C38C 1.421(10)
C34C C35C 1.379(9)
C34C H34C 0.9500
C35C C36C 1.384(10)
C35C H35C 0.9500
C36C C37C 1.354(9)
C36C H36C 0.9500
C37C C38C 1.406(10)
C37C H37C 0.9500
C38C N5C 1.427(10)
N6C C40C 1.379(9)
C39C C44C 1.410(9)
C39C C40C 1.419(9)
C40C C41C 1.399(9)
C41C C42C 1.355(10)
C41C H41C 0.9500
C42C C43C 1.399(10)
C42C H42C 0.9500
C43C C44C 1.390(9)
C43C H43C 0.9500
C44C H44C 0.9500
O1D N6D 1.263(11)
C1D N1D 1.356(11)
C1D C20D 1.405(10)
C1D C2D 1.414(11)
C2D C3D 1.361(11)
C2D H2D 0.9500
C3D C4D 1.423(11)
C3D H3D 0.9500
C4D N1D 1.390(11)
N1D H1D 0.8800
C15D C16D 1.412(11)
C15D C33D 1.470(10)
C16D N4D 1.361(14)
C16D C17D 1.447(11)
C17D N5D 1.311(13)
C17D C18D 1.427(10)
C18D N6D 1.342(14)
C18D C19D 1.455(11)
C19D N4D 1.377(16)
C19D C20D 1.387(8)
C20D C39D 1.457(10)
C33D C34D 1.401(8)
C33D C38D 1.427(11)
C34D C35D 1.374(10)
C34D H34D 0.9500
C35D C36D 1.387(11)
C35D H35D 0.9500
C36D C37D 1.369(10)
C36D H36D 0.9500
C37D C38D 1.407(11)
C37D H37D 0.9500
C38D N5D 1.395(10)
N6D C40D 1.401(10)
C39D C44D 1.389(10)
C39D C40D 1.424(10)
C40D C41D 1.392(10)
C41D C42D 1.368(12)
C41D H41D 0.9500
C42D C43D 1.402(10)
C42D H42D 0.9500
C43D C44D 1.386(10)
C43D H43D 0.9500
C44D H44D 0.9500
N1A H1A 0.8800
N3A H3A1 0.8800
N5A O1A 1.189(8)
N6A O1B 1.266(3)
N3C H3C1 0.8800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1A C1A C2A C3A -0.6(3)
C20A C1A C2A C3A -172.1(3)
C1A C2A C3A C4A 0.1(4)
C2A C3A C4A N1A 0.4(3)
C2A C3A C4A C5A 178.6(3)
N1A C4A C5A C6A 6.0(5)
C3A C4A C5A C6A -171.9(3)
N1A C4A C5A C21A -173.8(3)
C3A C4A C5A C21A 8.3(5)
C4A C5A C6A N2A 6.1(5)
C21A C5A C6A N2A -174.0(3)
C4A C5A C6A C7A -172.6(3)
C21A C5A C6A C7A 7.2(5)
N2A C6A C7A C8A -0.5(4)
C5A C6A C7A C8A 178.4(3)
C6A C7A C8A C9A 0.7(4)
C7A C8A C9A N2A -0.7(4)
C7A C8A C9A C10A 176.4(3)
N2A C9A C10A C11A 8.1(5)
C8A C9A C10A C11A -168.6(3)
N2A C9A C10A C27A -174.0(3)
C8A C9A C10A C27A 9.4(4)
C9A C10A C11A N3A 0.9(5)
C27A C10A C11A N3A -177.0(3)
C9A C10A C11A C12A 178.1(3)
C27A C10A C11A C12A 0.2(4)
N3A C11A C12A C13A 2.4(3)
C10A C11A C12A C13A -175.2(3)
C11A C12A C13A C14A -1.2(3)
C12A C13A C14A N3A -0.5(3)
C12A C13A C14A C15A -176.5(3)
N3A C14A C15A C16A -22.1(4)
C13A C14A C15A C16A 153.4(3)
N3A C14A C15A C33A 154.4(3)
C13A C14A C15A C33A -30.2(4)
C14A C15A C16A N4A 9.7(4)
C33A C15A C16A N4A -167.0(3)
C14A C15A C16A C17A -171.1(2)
C33A C15A C16A C17A 12.2(4)
N4A C16A C17A N5A 174.3(2)
C15A C16A C17A N5A -5.0(4)
N4A C16A C17A C18A -1.5(3)
C15A C16A C17A C18A 179.2(2)
N5A C17A C18A N6A 1.3(5)
C16A C17A C18A N6A 177.0(3)
N5A C17A C18A C19A -172.7(3)
C16A C17A C18A C19A 3.0(3)
N6A C18A C19A N4A -178.1(2)
C17A C18A C19A N4A -3.7(3)
N6A C18A C19A C20A -5.6(4)
C17A C18A C19A C20A 168.8(2)
N4A C19A C20A C1A 14.4(5)
C18A C19A C20A C1A -156.6(3)
N4A C19A C20A C39A -176.3(3)
C18A C19A C20A C39A 12.7(4)
N1A C1A C20A C19A -21.7(4)
C2A C1A C20A C19A 148.5(3)
N1A C1A C20A C39A 169.5(3)
C2A C1A C20A C39A -20.3(5)
C4A C5A C21A C26A -124.4(3)
C6A C5A C21A C26A 55.8(4)
C4A C5A C21A C22A 56.2(4)
C6A C5A C21A C22A -123.7(3)
C26A C21A C22A C23A -0.2(4)
C5A C21A C22A C23A 179.3(2)
C21A C22A C23A C24A 0.9(4)
C22A C23A C24A C25A -1.0(5)
C23A C24A C25A C26A 0.5(5)
C22A C21A C26A C25A -0.4(4)
C5A C21A C26A C25A -179.8(2)
C24A C25A C26A C21A 0.2(4)
C11A C10A C27A C32A 62.4(4)
C9A C10A C27A C32A -115.7(3)
C11A C10A C27A C28A -119.0(3)
C9A C10A C27A C28A 62.9(4)
C32A C27A C28A C29A -0.8(4)
C10A C27A C28A C29A -179.4(3)
C27A C28A C29A C30A 1.0(5)
C28A C29A C30A C31A -0.6(5)
C29A C30A C31A C32A 0.0(5)
C28A C27A C32A C31A 0.2(4)
C10A C27A C32A C31A 178.8(3)
C30A C31A C32A C27A 0.2(5)
C16A C15A C33A C38A -11.7(4)
C14A C15A C33A C38A 171.6(2)
C16A C15A C33A C34A 161.6(2)
C14A C15A C33A C34A -15.1(4)
C38A C33A C34A C35A -3.1(4)
C15A C33A C34A C35A -176.7(3)
C33A C34A C35A C36A -1.4(4)
C34A C35A C36A C37A 3.6(4)
C35A C36A C37A C38A -1.0(4)
C36A C37A C38A N5A 172.4(2)
C36A C37A C38A C33A -3.7(4)
C34A C33A C38A N5A -170.1(2)
C15A C33A C38A N5A 3.6(4)
C34A C33A C38A C37A 5.7(4)
C15A C33A C38A C37A 179.4(2)
C19A C20A C39A C44A 166.5(3)
C1A C20A C39A C44A -24.1(4)
C19A C20A C39A C40A -11.3(4)
C1A C20A C39A C40A 158.1(3)
C44A C39A C40A C41A 5.7(4)
C20A C39A C40A C41A -176.3(3)
C44A C39A C40A N6A -175.6(3)
C20A C39A C40A N6A 2.4(4)
N6A C40A C41A C42A 179.6(3)
C39A C40A C41A C42A -1.6(5)
C40A C41A C42A C43A -2.6(5)
C41A C42A C43A C44A 2.4(5)
C42A C43A C44A C39A 2.1(5)
C40A C39A C44A C43A -5.9(5)
C20A C39A C44A C43A 176.2(3)
C4D C5C C6C N2C -9.5(17)
C4C C5C C6C N2C -8.0(12)
C21C C5C C6C N2C 170.3(2)
C4D C5C C6C C7C 170.1(16)
C4C C5C C6C C7C 171.6(12)
C21C C5C C6C C7C -10.1(4)
N2C C6C C7C C8C 0.4(3)
C5C C6C C7C C8C -179.2(3)
C6C C7C C8C C9C -0.9(3)
C7C C8C C9C N2C 1.0(3)
C7C C8C C9C C10C -174.5(2)
N2C C9C C10C C11C 0.0(4)
C8C C9C C10C C11C 174.9(3)
N2C C9C C10C C27C -177.1(2)
C8C C9C C10C C27C -2.2(4)
C9C C10C C11C N3C -6.2(4)
C27C C10C C11C N3C 170.9(2)
C9C C10C C11C C12C 172.3(3)
C27C C10C C11C C12C -10.6(4)
N3C C11C C12C C13C -0.8(3)
C10C C11C C12C C13C -179.6(3)
C11C C12C C13C C14C -0.7(3)
C12C C13C C14C N3C 1.9(3)
C12C C13C C14C C15C -176.3(13)
C12C C13C C14C C15D 169.9(15)
C4D C5C C21C C22C -59.8(13)
C6C C5C C21C C22C 120.4(3)
C4C C5C C21C C22C -61.4(13)
C4D C5C C21C C26C 118.6(13)
C6C C5C C21C C26C -61.2(4)
C4C C5C C21C C26C 117.0(13)
C26C C21C C22C C23C -0.3(4)
C5C C21C C22C C23C 178.1(3)
C21C C22C C23C C24C -0.5(4)
C22C C23C C24C C25C 0.2(5)
C23C C24C C25C C26C 1.0(4)
C24C C25C C26C C21C -1.8(4)
C22C C21C C26C C25C 1.5(4)
C5C C21C C26C C25C -177.0(3)
C11C C10C C27C C32C -67.8(3)
C9C C10C C27C C32C 109.6(3)
C11C C10C C27C C28C 114.2(3)
C9C C10C C27C C28C -68.4(3)
C32C C27C C28C C29C 1.7(4)
C10C C27C C28C C29C 179.8(2)
C27C C28C C29C C30C -2.0(4)
C28C C29C C30C C31C 0.8(4)
C29C C30C C31C C32C 0.6(4)
C28C C27C C32C C31C -0.3(4)
C10C C27C C32C C31C -178.4(2)
C30C C31C C32C C27C -0.9(4)
N1C C1C C2C C3C 2(4)
C20C C1C C2C C3C 174(3)
C1C C2C C3C C4C 0(4)
C4D C5C C4C N1C 172(11)
C6C C5C C4C N1C -4(4)
C21C C5C C4C N1C 178(3)
C4D C5C C4C C3C -8(7)
C6C C5C C4C C3C 176(2)
C21C C5C C4C C3C -2(3)
C2C C3C C4C N1C -2(3)
C2C C3C C4C C5C 178(2)
C2C C1C N1C C4C -3(4)
C20C C1C N1C C4C -176(2)
C5C C4C N1C C1C -177(3)
C3C C4C N1C C1C 3(4)
N3C C14C C15C C16C 24(3)
C13C C14C C15C C16C -158.0(15)
C15D C14C C15C C16C -16(7)
N3C C14C C15C C33C -165.3(15)
C13C C14C C15C C33C 12(3)
C15D C14C C15C C33C 155(10)
C14C C15C C16C N4C -11(4)
C33C C15C C16C N4C 178(2)
C14C C15C C16C C17C 164(2)
C33C C15C C16C C17C -7(4)
N4C C16C C17C N5C 180(2)
C15C C16C C17C N5C 3(4)
N4C C16C C17C C18C 1(3)
C15C C16C C17C C18C -175(2)
N5C C17C C18C N6C -1(5)
C16C C17C C18C N6C 177.6(17)
N5C C17C C18C C19C -177(3)
C16C C17C C18C C19C 2(3)
N6C C18C C19C N4C -179.9(17)
C17C C18C C19C N4C -4(2)
N6C C18C C19C C20C 6(3)
C17C C18C C19C C20C -178.5(19)
N4C C19C C20C C1C -14(3)
C18C C19C C20C C1C 159(2)
N4C C19C C20C C39C 178(2)
C18C C19C C20C C39C -9(2)
N1C C1C C20C C19C 24(4)
C2C C1C C20C C19C -147(3)
N1C C1C C20C C39C -168(2)
C2C C1C C20C C39C 21(4)
C20C C19C N4C C16C 178.1(19)
C18C C19C N4C C16C 5(2)
C15C C16C N4C C19C 173(2)
C17C C16C N4C C19C -3(3)
C16C C15C C33C C34C -175.0(19)
C14C C15C C33C C34C 15(3)
C16C C15C C33C C38C 4(3)
C14C C15C C33C C38C -165.9(18)
C38C C33C C34C C35C -1(2)
C15C C33C C34C C35C 178.4(19)
C33C C34C C35C C36C 1(2)
C34C C35C C36C C37C -1(2)
C35C C36C C37C C38C 2(3)
C36C C37C C38C C33C -2(2)
C36C C37C C38C N5C 178.1(16)
C34C C33C C38C C37C 2(2)
C15C C33C C38C C37C -177.5(18)
C34C C33C C38C N5C -178.7(15)
C15C C33C C38C N5C 2(3)
C18C C17C N5C O1C 1(4)
C16C C17C N5C O1C -177(2)
C18C C17C N5C C38C -179(3)
C16C C17C N5C C38C 3(4)
C37C C38C N5C O1C -6(2)
C33C C38C N5C O1C 174.9(13)
C37C C38C N5C C17C 174(2)
C33C C38C N5C C17C -6(3)
C17C C18C N6C C40C -175(2)
C19C C18C N6C C40C 0(2)
C19C C20C C39C C44C -162.9(14)
C1C C20C C39C C44C 28(2)
C19C C20C C39C C40C 8.2(18)
C1C C20C C39C C40C -160.8(17)
C18C N6C C40C C41C 176.9(12)
C18C N6C C40C C39C -1.1(18)
C44C C39C C40C N6C 168.6(12)
C20C C39C C40C N6C -3.0(17)
C44C C39C C40C C41C -9.4(17)
C20C C39C C40C C41C 179.1(10)
N6C C40C C41C C42C -173.6(10)
C39C C40C C41C C42C 4.5(15)
C40C C41C C42C C43C 3.1(14)
C41C C42C C43C C44C -5.4(14)
C42C C43C C44C C39C 0.1(17)
C40C C39C C44C C43C 7.1(18)
C20C C39C C44C C43C 178.3(11)
N1D C1D C2D C3D 0(4)
C20D C1D C2D C3D 173(3)
C1D C2D C3D C4D 0(4)
C6C C5C C4D N1D -5(3)
C4C C5C C4D N1D -10(7)
C21C C5C C4D N1D 175(2)
C6C C5C C4D C3D 177(3)
C4C C5C C4D C3D 172(12)
C21C C5C C4D C3D -3(4)
C2D C3D C4D N1D -1(4)
C2D C3D C4D C5C 177(3)
C20D C1D N1D C4D -173(3)
C2D C1D N1D C4D -1(4)
C5C C4D N1D C1D -178(2)
C3D C4D N1D C1D 1(4)
N3C C14C C15D C16D 11(3)
C13C C14C C15D C16D -156(2)
C15C C14C C15D C16D 157(11)
N3C C14C C15D C33D -167.3(17)
C13C C14C C15D C33D 26(3)
C15C C14C C15D C33D -21(6)
C14C C15D C16D N4D -1(5)
C33D C15D C16D N4D 177(3)
C14C C15D C16D C17D 169(3)
C33D C15D C16D C17D -13(4)
N4D C16D C17D N5D -178(3)
C15D C16D C17D N5D 10(5)
N4D C16D C17D C18D 6(3)
C15D C16D C17D C18D -166(2)
N5D C17D C18D N6D 4(5)
C16D C17D C18D N6D -180(2)
N5D C17D C18D C19D 177(3)
C16D C17D C18D C19D -7(3)
N6D C18D C19D N4D 179.7(18)
C17D C18D C19D N4D 6(3)
N6D C18D C19D C20D 2(3)
C17D C18D C19D C20D -172(2)
N4D C19D C20D C1D -10(4)
C18D C19D C20D C1D 168(2)
N4D C19D C20D C39D 169(2)
C18D C19D C20D C39D -14(2)
N1D C1D C20D C19D 21(4)
C2D C1D C20D C19D -150(3)
N1D C1D C20D C39D -157(3)
C2D C1D C20D C39D 32(4)
C15D C16D N4D C19D 168(3)
C17D C16D N4D C19D -2(3)
C20D C19D N4D C16D 175(2)
C18D C19D N4D C16D -2(3)
C16D C15D C33D C34D -166(2)
C14C C15D C33D C34D 12(3)
C16D C15D C33D C38D 8(3)
C14C C15D C33D C38D -173.1(17)
C38D C33D C34D C35D 6(2)
C15D C33D C34D C35D -179(2)
C33D C34D C35D C36D -5(3)
C34D C35D C36D C37D 1(3)
C35D C36D C37D C38D 0(3)
C36D C37D C38D N5D -178.0(18)
C36D C37D C38D C33D 2(3)
C34D C33D C38D N5D 175.5(18)
C15D C33D C38D N5D 0(3)
C34D C33D C38D C37D -5(2)
C15D C33D C38D C37D -180(2)
C18D C17D N5D C38D 175(3)
C16D C17D N5D C38D -1(4)
C37D C38D N5D C17D 176(2)
C33D C38D N5D C17D -5(3)
C17D C18D N6D O1D -5(3)
C19D C18D N6D O1D -177.2(15)
C17D C18D N6D C40D 180(2)
C19D C18D N6D C40D 7(2)
C19D C20D C39D C44D -164.4(16)
C1D C20D C39D C44D 14(3)
C19D C20D C39D C40D 18(2)
C1D C20D C39D C40D -164(2)
O1D N6D C40D C41D -1.3(17)
C18D N6D C40D C41D 174.6(13)
O1D N6D C40D C39D -178.9(11)
C18D N6D C40D C39D -3(2)
C44D C39D C40D C41D -5.1(19)
C20D C39D C40D C41D 172.4(12)
C44D C39D C40D N6D 172.4(13)
C20D C39D C40D N6D -10.1(19)
N6D C40D C41D C42D -174.1(11)
C39D C40D C41D C42D 3.4(17)
C40D C41D C42D C43D 0.7(16)
C41D C42D C43D C44D -3.0(16)
C42D C43D C44D C39D 1.2(19)
C40D C39D C44D C43D 3(2)
C20D C39D C44D C43D -174.8(12)
C20A C1A N1A C4A 172.7(3)
C2A C1A N1A C4A 0.8(3)
C5A C4A N1A C1A -178.9(3)
C3A C4A N1A C1A -0.7(3)
C5A C6A N2A C9A -178.8(3)
C7A C6A N2A C9A 0.1(3)
C10A C9A N2A C6A -176.7(3)
C8A C9A N2A C6A 0.3(3)
C13A C14A N3A C11A 2.0(3)
C15A C14A N3A C11A 178.3(2)
C10A C11A N3A C14A 175.0(3)
C12A C11A N3A C14A -2.7(3)
C20A C19A N4A C16A -168.9(3)
C18A C19A N4A C16A 2.7(3)
C15A C16A N4A C19A 178.5(3)
C17A C16A N4A C19A -0.7(3)
C18A C17A N5A O1A -12.2(7)
C16A C17A N5A O1A 173.0(6)
C18A C17A N5A C38A 171.0(3)
C16A C17A N5A C38A -3.8(4)
C37A C38A N5A O1A 11.0(6)
C33A C38A N5A O1A -173.0(5)
C37A C38A N5A C17A -171.7(2)
C33A C38A N5A C17A 4.3(4)
C17A C18A N6A O1B 5.2(5)
C19A C18A N6A O1B 178.2(3)
C17A C18A N6A C40A -176.8(3)
C19A C18A N6A C40A -3.8(4)
C41A C40A N6A O1B 2.2(4)
C39A C40A N6A O1B -176.6(3)
C41A C40A N6A C18A -175.9(3)
C39A C40A N6A C18A 5.3(4)
C5C C6C N2C C9C 179.9(3)
C7C C6C N2C C9C 0.2(3)
C10C C9C N2C C6C 174.7(2)
C8C C9C N2C C6C -0.8(3)
C13C C14C N3C C11C -2.4(3)
C15C C14C N3C C11C 175.6(13)
C15D C14C N3C C11C -173.2(13)
C10C C11C N3C C14C -179.2(3)
C12C C11C N3C C14C 2.0(3)
|
1501987.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501987.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501987
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Dange, Nitin S.'
'Hsu, Che-Sheng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
Dynamic kinetic asymmetric synthesis of five contiguous stereogenic
centers by sequential organocatalytic stetter and Michael-aldol reaction:
enantioselective synthesis of fully substituted cyclopentanols bearing a
quaternary stereocenter.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1338
_journal_page_last 1341
_journal_paper_doi 10.1021/ol200006e
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_sum 'C23 H27 Cl N2 O4'
_chemical_formula_weight 430.92
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 5.8373(4)
_cell_length_b 18.1668(13)
_cell_length_c 21.7172(15)
_cell_measurement_reflns_used 934
_cell_measurement_temperature 295(2)
_cell_measurement_theta_max 23.529
_cell_measurement_theta_min -23.529
_cell_volume 2303.0(3)
_computing_cell_refinement 'BRUKER SMART'
_computing_data_collection 'BRUKER SMART'
_computing_data_reduction 'BRUKER SAINT'
_computing_molecular_graphics Ortep-3
_computing_publication_material 'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 295(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type 'Bruker Smart Apex'
_diffrn_measurement_method 'phi-omega scan'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0287
_diffrn_reflns_av_sigmaI/netI 0.0377
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 20313
_diffrn_reflns_theta_full 28.30
_diffrn_reflns_theta_max 28.30
_diffrn_reflns_theta_min 1.88
_diffrn_standards_decay_% 0
_exptl_absorpt_coefficient_mu 0.196
_exptl_absorpt_correction_T_max 0.9959
_exptl_absorpt_correction_T_min 0.9799
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.243
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 912
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.06
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.256
_refine_diff_density_min -0.184
_refine_diff_density_rms 0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.02(10)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 273
_refine_ls_number_reflns 5533
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.047
_refine_ls_R_factor_all 0.0849
_refine_ls_R_factor_gt 0.0556
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.1388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1318
_refine_ls_wR_factor_ref 0.1464
_reflns_number_gt 3805
_reflns_number_total 5533
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200006e_si_002.cif
_cod_data_source_block hcs269f2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_Hall P2ac2ab
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1501987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.30447(17) 0.44715(5) 0.24852(4) 0.0986(3) Uani 1 1 d .
O1 O 0.5273(4) 0.10953(13) 0.30730(10) 0.0793(6) Uani 1 1 d .
O2 O 0.2689(5) 0.10362(16) 0.23822(9) 0.1008(8) Uani 1 1 d .
O3 O -0.2457(4) 0.22408(13) 0.45495(9) 0.0783(6) Uani 1 1 d .
O4 O -0.1303(3) 0.04123(10) 0.44220(8) 0.0593(4) Uani 1 1 d .
H4 H -0.1609 0.0159 0.4724 0.089 Uiso 1 1 calc R
N1 N 0.3320(4) 0.09999(11) 0.29111(9) 0.0574(5) Uani 1 1 d .
N2 N 0.0589(4) 0.00869(13) 0.54535(10) 0.0670(6) Uani 1 1 d .
C1 C 0.142(3) -0.3357(5) 0.3930(6) 0.360(9) Uani 1 1 d D
H1A H 0.1299 -0.3650 0.4296 0.539 Uiso 1 1 calc R
H1B H 0.1413 -0.3672 0.3575 0.539 Uiso 1 1 calc R
H1C H 0.0137 -0.3025 0.3908 0.539 Uiso 1 1 calc R
C2 C 0.338(3) -0.2966(4) 0.3944(6) 0.317(8) Uani 1 1 d D
H2A H 0.4147 -0.2972 0.3547 0.380 Uiso 1 1 calc R
H2B H 0.4423 -0.3152 0.4256 0.380 Uiso 1 1 calc R
C3 C 0.244(2) -0.2131(4) 0.4118(4) 0.252(6) Uani 1 1 d D
H3A H 0.1150 -0.2000 0.3860 0.302 Uiso 1 1 calc R
H3B H 0.1964 -0.2110 0.4546 0.302 Uiso 1 1 calc R
C4 C 0.4195(17) -0.1672(3) 0.4020(3) 0.179(3) Uani 1 1 d D
H4A H 0.4516 -0.1670 0.3581 0.215 Uiso 1 1 calc R
H4B H 0.5533 -0.1873 0.4224 0.215 Uiso 1 1 calc R
C5 C 0.3921(10) -0.08792(18) 0.42264(18) 0.1102(14) Uani 1 1 d .
H5A H 0.5419 -0.0650 0.4245 0.132 Uiso 1 1 calc R
H5B H 0.3277 -0.0873 0.4638 0.132 Uiso 1 1 calc R
C6 C 0.2380(6) -0.04283(14) 0.37991(13) 0.0704(8) Uani 1 1 d .
H6A H 0.0819 -0.0605 0.3839 0.084 Uiso 1 1 calc R
H6B H 0.2857 -0.0512 0.3377 0.084 Uiso 1 1 calc R
C7 C 0.2415(4) 0.04013(12) 0.39262(10) 0.0490(5) Uani 1 1 d .
H7 H 0.4010 0.0549 0.3995 0.059 Uiso 1 1 calc R
C8 C 0.0986(4) 0.06786(12) 0.44723(10) 0.0453(5) Uani 1 1 d .
C9 C 0.0876(4) 0.15174(12) 0.43418(9) 0.0426(5) Uani 1 1 d .
H9 H 0.2369 0.1736 0.4437 0.051 Uiso 1 1 calc R
C10 C 0.0457(4) 0.15742(12) 0.36491(10) 0.0451(5) Uani 1 1 d .
H10 H -0.1205 0.1540 0.3591 0.054 Uiso 1 1 calc R
C11 C 0.1486(4) 0.08481(13) 0.33858(10) 0.0494(5) Uani 1 1 d .
H11 H 0.0254 0.0567 0.3189 0.059 Uiso 1 1 calc R
C12 C 0.1195(4) 0.22910(13) 0.33520(9) 0.0453(5) Uani 1 1 d .
C13 C 0.3252(4) 0.26264(13) 0.34783(11) 0.0525(6) Uani 1 1 d .
H13 H 0.4259 0.2404 0.3753 0.063 Uiso 1 1 calc R
C14 C 0.3868(5) 0.32928(15) 0.32045(12) 0.0627(7) Uani 1 1 d .
H14 H 0.5267 0.3514 0.3293 0.075 Uiso 1 1 calc R
C15 C 0.2358(5) 0.36134(15) 0.28020(13) 0.0644(7) Uani 1 1 d .
C16 C 0.0329(6) 0.32931(18) 0.26583(13) 0.0711(8) Uani 1 1 d .
H16 H -0.0657 0.3515 0.2378 0.085 Uiso 1 1 calc R
C17 C -0.0257(5) 0.26329(16) 0.29332(12) 0.0593(6) Uani 1 1 d .
H17 H -0.1650 0.2413 0.2836 0.071 Uiso 1 1 calc R
C18 C -0.0907(5) 0.18745(13) 0.47338(11) 0.0514(6) Uani 1 1 d .
H18 H -0.0800 0.1805 0.5157 0.062 Uiso 1 1 calc R
C19 C 0.1937(4) 0.04979(13) 0.51028(10) 0.0466(5) Uani 1 1 d .
C20 C 0.4041(4) 0.07424(16) 0.53017(11) 0.0584(6) Uani 1 1 d .
H20 H 0.4951 0.1032 0.5047 0.070 Uiso 1 1 calc R
C21 C 0.4778(5) 0.0554(2) 0.58777(13) 0.0747(8) Uani 1 1 d .
H21 H 0.6195 0.0715 0.6019 0.090 Uiso 1 1 calc R
C22 C 0.3419(6) 0.01263(18) 0.62455(13) 0.0785(9) Uani 1 1 d .
H22 H 0.3887 -0.0009 0.6639 0.094 Uiso 1 1 calc R
C23 C 0.1357(6) -0.00955(19) 0.60174(14) 0.0814(9) Uani 1 1 d .
H23 H 0.0431 -0.0389 0.6265 0.098 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1089(7) 0.0792(5) 0.1076(6) 0.0419(5) 0.0198(5) -0.0042(5)
O1 0.0577(12) 0.1006(16) 0.0797(13) -0.0023(12) 0.0090(10) -0.0106(11)
O2 0.1221(19) 0.138(2) 0.0428(10) -0.0112(11) 0.0047(12) -0.0074(17)
O3 0.0697(12) 0.0920(14) 0.0730(12) -0.0111(10) 0.0033(10) 0.0296(12)
O4 0.0485(9) 0.0630(11) 0.0665(10) 0.0000(8) -0.0036(8) -0.0181(8)
N1 0.0751(16) 0.0549(12) 0.0423(11) -0.0126(9) 0.0070(10) -0.0026(11)
N2 0.0704(14) 0.0677(14) 0.0629(13) 0.0115(11) 0.0062(12) -0.0145(12)
C1 0.365(18) 0.109(6) 0.60(2) -0.046(10) -0.071(19) -0.022(9)
C2 0.415(19) 0.073(4) 0.462(17) -0.056(7) -0.001(17) -0.035(7)
C3 0.396(16) 0.090(4) 0.271(9) -0.028(5) 0.009(10) -0.077(7)
C4 0.296(10) 0.067(3) 0.175(5) 0.001(3) -0.008(6) 0.051(4)
C5 0.164(4) 0.0519(18) 0.114(3) -0.0075(17) -0.013(3) 0.026(2)
C6 0.092(2) 0.0484(14) 0.0705(16) -0.0147(12) 0.0067(15) 0.0014(14)
C7 0.0526(13) 0.0450(12) 0.0493(12) -0.0087(10) 0.0007(10) -0.0025(10)
C8 0.0408(12) 0.0444(12) 0.0506(12) -0.0023(10) 0.0011(10) -0.0054(10)
C9 0.0402(11) 0.0434(11) 0.0443(11) -0.0052(9) -0.0021(9) -0.0034(10)
C10 0.0398(11) 0.0503(13) 0.0451(12) -0.0041(10) -0.0030(9) -0.0017(10)
C11 0.0513(13) 0.0506(13) 0.0463(12) -0.0088(10) -0.0050(10) -0.0081(10)
C12 0.0458(12) 0.0508(13) 0.0394(10) -0.0035(9) 0.0009(10) 0.0065(10)
C13 0.0482(13) 0.0527(13) 0.0565(13) 0.0031(11) -0.0034(11) 0.0001(11)
C14 0.0558(15) 0.0584(15) 0.0739(17) 0.0037(13) 0.0050(13) -0.0053(13)
C15 0.0718(18) 0.0609(15) 0.0603(15) 0.0114(12) 0.0178(14) 0.0025(14)
C16 0.0762(19) 0.0812(19) 0.0560(16) 0.0221(15) -0.0067(14) 0.0091(16)
C17 0.0548(14) 0.0685(17) 0.0547(14) 0.0070(13) -0.0081(11) -0.0045(13)
C18 0.0518(14) 0.0521(14) 0.0503(13) -0.0059(10) 0.0023(11) -0.0013(12)
C19 0.0495(13) 0.0431(11) 0.0473(12) 0.0011(9) 0.0043(10) -0.0022(11)
C20 0.0506(14) 0.0720(16) 0.0524(14) 0.0091(12) -0.0015(11) -0.0086(13)
C21 0.0659(17) 0.096(2) 0.0619(17) 0.0054(16) -0.0132(13) -0.0034(17)
C22 0.091(2) 0.091(2) 0.0532(15) 0.0187(15) -0.0095(16) 0.0007(19)
C23 0.092(2) 0.085(2) 0.0677(17) 0.0294(16) 0.0105(18) -0.0095(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O4 H4 109.5
O1 N1 O2 123.9(2)
O1 N1 C11 119.8(2)
O2 N1 C11 116.3(2)
C19 N2 C23 117.6(2)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C1 C2 C3 101.8(11)
C1 C2 H2A 111.4
C3 C2 H2A 111.4
C1 C2 H2B 111.4
C3 C2 H2B 111.4
H2A C2 H2B 109.3
C4 C3 C2 106.3(10)
C4 C3 H3A 110.5
C2 C3 H3A 110.5
C4 C3 H3B 110.5
C2 C3 H3B 110.5
H3A C3 H3B 108.7
C3 C4 C5 117.6(7)
C3 C4 H4A 107.9
C5 C4 H4A 107.9
C3 C4 H4B 107.9
C5 C4 H4B 107.9
H4A C4 H4B 107.2
C4 C5 C6 113.0(4)
C4 C5 H5A 109.0
C6 C5 H5A 109.0
C4 C5 H5B 109.0
C6 C5 H5B 109.0
H5A C5 H5B 107.8
C5 C6 C7 114.2(3)
C5 C6 H6A 108.7
C7 C6 H6A 108.7
C5 C6 H6B 108.7
C7 C6 H6B 108.7
H6A C6 H6B 107.6
C11 C7 C6 112.3(2)
C11 C7 C8 103.08(18)
C6 C7 C8 117.1(2)
C11 C7 H7 108.0
C6 C7 H7 108.0
C8 C7 H7 108.0
O4 C8 C19 109.86(18)
O4 C8 C7 109.81(18)
C19 C8 C7 115.35(18)
O4 C8 C9 106.31(18)
C19 C8 C9 113.17(17)
C7 C8 C9 101.76(17)
C18 C9 C10 114.9(2)
C18 C9 C8 110.57(18)
C10 C9 C8 104.64(16)
C18 C9 H9 108.9
C10 C9 H9 108.9
C8 C9 H9 108.9
C12 C10 C9 115.57(18)
C12 C10 C11 117.49(18)
C9 C10 C11 104.03(18)
C12 C10 H10 106.3
C9 C10 H10 106.3
C11 C10 H10 106.3
N1 C11 C7 111.7(2)
N1 C11 C10 111.64(18)
C7 C11 C10 107.76(17)
N1 C11 H11 108.5
C7 C11 H11 108.5
C10 C11 H11 108.5
C13 C12 C17 117.7(2)
C13 C12 C10 123.0(2)
C17 C12 C10 119.3(2)
C12 C13 C14 121.6(2)
C12 C13 H13 119.2
C14 C13 H13 119.2
C15 C14 C13 118.3(3)
C15 C14 H14 120.8
C13 C14 H14 120.8
C16 C15 C14 121.7(3)
C16 C15 Cl1 119.5(2)
C14 C15 Cl1 118.8(2)
C15 C16 C17 119.3(3)
C15 C16 H16 120.4
C17 C16 H16 120.4
C16 C17 C12 121.3(3)
C16 C17 H17 119.4
C12 C17 H17 119.4
O3 C18 C9 125.5(2)
O3 C18 H18 117.3
C9 C18 H18 117.3
N2 C19 C20 122.1(2)
N2 C19 C8 115.1(2)
C20 C19 C8 122.8(2)
C21 C20 C19 119.2(2)
C21 C20 H20 120.4
C19 C20 H20 120.4
C20 C21 C22 119.6(3)
C20 C21 H21 120.2
C22 C21 H21 120.2
C23 C22 C21 117.9(3)
C23 C22 H22 121.1
C21 C22 H22 121.1
N2 C23 C22 123.5(3)
N2 C23 H23 118.2
C22 C23 H23 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C15 1.750(3)
O1 N1 1.205(3)
O2 N1 1.208(3)
O3 C18 1.192(3)
O4 C8 1.425(3)
O4 H4 0.8200
N1 C11 1.511(3)
N2 C19 1.326(3)
N2 C23 1.346(4)
C1 C2 1.350(14)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.657(11)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.337(11)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.517(6)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.530(5)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.532(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C11 1.526(3)
C7 C8 1.535(3)
C7 H7 0.9800
C8 C19 1.514(3)
C8 C9 1.551(3)
C9 C18 1.493(3)
C9 C10 1.528(3)
C9 H9 0.9800
C10 C12 1.516(3)
C10 C11 1.558(3)
C10 H10 0.9800
C11 H11 0.9800
C12 C13 1.374(3)
C12 C17 1.390(3)
C13 C14 1.396(4)
C13 H13 0.9300
C14 C15 1.371(4)
C14 H14 0.9300
C15 C16 1.356(4)
C16 C17 1.383(4)
C16 H16 0.9300
C17 H17 0.9300
C18 H18 0.9300
C19 C20 1.375(3)
C20 C21 1.366(4)
C20 H20 0.9300
C21 C22 1.368(4)
C21 H21 0.9300
C22 C23 1.362(5)
C22 H22 0.9300
C23 H23 0.9300
|
1501988.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501988.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501988
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Dange, Nitin S.'
'Hsu, Che-Sheng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
Dynamic kinetic asymmetric synthesis of five contiguous stereogenic
centers by sequential organocatalytic stetter and Michael-aldol reaction:
enantioselective synthesis of fully substituted cyclopentanols bearing a
quaternary stereocenter.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1338
_journal_page_last 1341
_journal_paper_doi 10.1021/ol200006e
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_sum 'C23 H25 Br N2 O4'
_chemical_formula_weight 473.36
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 5.8869(4)
_cell_length_b 12.4397(9)
_cell_length_c 30.019(2)
_cell_measurement_reflns_used 999
_cell_measurement_temperature 295(2)
_cell_measurement_theta_max 23.529
_cell_measurement_theta_min -23.529
_cell_volume 2198.3(3)
_computing_cell_refinement 'BRUKER SMART'
_computing_data_collection 'BRUKER SMART'
_computing_data_reduction 'BRUKER SAINT'
_computing_molecular_graphics Ortep-3
_computing_publication_material 'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type 'Bruker Smart Apex'
_diffrn_measurement_method 'phi-omega scan'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0273
_diffrn_reflns_av_sigmaI/netI 0.0360
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 39
_diffrn_reflns_limit_l_min -38
_diffrn_reflns_number 25670
_diffrn_reflns_theta_full 28.32
_diffrn_reflns_theta_max 28.32
_diffrn_reflns_theta_min 1.36
_diffrn_standards_decay_% 0
_exptl_absorpt_coefficient_mu 1.901
_exptl_absorpt_correction_T_max 0.8674
_exptl_absorpt_correction_T_min 0.6448
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.430
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description columnar
_exptl_crystal_F_000 976
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.472
_refine_diff_density_min -0.279
_refine_diff_density_rms 0.125
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.005(7)
_refine_ls_extinction_coef 0.0012(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.966
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 284
_refine_ls_number_reflns 5329
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.966
_refine_ls_R_factor_all 0.0524
_refine_ls_R_factor_gt 0.0350
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0766
_refine_ls_wR_factor_ref 0.0890
_reflns_number_gt 4006
_reflns_number_total 5329
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200006e_si_003.cif
_cod_data_source_block hcs2121f1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_Hall P2ac2ab
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1501988
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.70300(7) 1.22589(2) 0.599336(9) 0.07262(14) Uani 1 1 d .
O1 O 0.3227(3) 0.82075(15) 0.36335(6) 0.0496(4) Uani 1 1 d .
H1 H 0.291(7) 0.759(3) 0.3503(13) 0.097(12) Uiso 1 1 d .
O2 O 0.1837(4) 0.83461(19) 0.47030(10) 0.0916(8) Uani 1 1 d .
O3 O 0.6790(6) 1.16495(19) 0.35627(11) 0.1124(10) Uani 1 1 d .
O4 O 0.3824(4) 1.07084(17) 0.34618(8) 0.0782(7) Uani 1 1 d .
N1 N 0.4579(4) 0.62294(18) 0.36083(8) 0.0556(6) Uani 1 1 d .
N2 N 0.5701(5) 1.08332(18) 0.36073(8) 0.0594(6) Uani 1 1 d .
C1 C 0.5435(4) 0.80743(18) 0.38168(8) 0.0377(5) Uani 1 1 d .
C2 C 0.5357(4) 0.84478(18) 0.43122(8) 0.0397(5) Uani 1 1 d .
H2 H 0.6801 0.8263 0.4455 0.048 Uiso 1 1 calc R
C3 C 0.5188(4) 0.96689(19) 0.42744(8) 0.0412(5) Uani 1 1 d .
H3 H 0.366(4) 0.9804(17) 0.4176(7) 0.028(5) Uiso 1 1 d .
C4 C 0.6775(5) 0.99395(18) 0.38765(7) 0.0428(5) Uani 1 1 d .
H4 H 0.8244 1.0185 0.3991 0.051 Uiso 1 1 calc R
C5 C 0.7127(4) 0.88757(18) 0.36099(7) 0.0393(5) Uani 1 1 d .
H5 H 0.8632 0.8615 0.3699 0.047 Uiso 1 1 calc R
C6 C 0.6119(4) 0.68901(19) 0.37851(8) 0.0400(5) Uani 1 1 d .
C7 C 0.8177(4) 0.6546(2) 0.39342(9) 0.0508(6) Uani 1 1 d .
H7 H 0.9208 0.7023 0.4060 0.061 Uiso 1 1 calc R
C8 C 0.8689(5) 0.5468(3) 0.38933(11) 0.0694(9) Uani 1 1 d .
H8 H 1.0091 0.5212 0.3988 0.083 Uiso 1 1 calc R
C9 C 0.7140(7) 0.4780(2) 0.37134(10) 0.0685(9) Uani 1 1 d .
H9 H 0.7462 0.4051 0.3688 0.082 Uiso 1 1 calc R
C10 C 0.5114(6) 0.5179(2) 0.35715(10) 0.0636(8) Uani 1 1 d .
H10 H 0.4064 0.4712 0.3445 0.076 Uiso 1 1 calc R
C11 C 0.7233(5) 0.8971(2) 0.30979(7) 0.0476(6) Uani 1 1 d .
H11 H 0.585(4) 0.9285(18) 0.2996(8) 0.034(6) Uiso 1 1 d .
C12 C 0.7364(6) 0.7879(2) 0.28679(8) 0.0656(8) Uani 1 1 d .
H12A H 0.6026 0.7462 0.2943 0.079 Uiso 1 1 calc R
H12B H 0.8685 0.7493 0.2976 0.079 Uiso 1 1 calc R
C13 C 0.7521(8) 0.7997(3) 0.23606(9) 0.0885(12) Uani 1 1 d .
H13A H 0.7671 0.7292 0.2226 0.106 Uiso 1 1 calc R
H13B H 0.6139 0.8324 0.2249 0.106 Uiso 1 1 calc R
C14 C 0.9521(8) 0.8678(4) 0.22338(11) 0.0971(13) Uani 1 1 d .
H14A H 0.9546 0.8769 0.1913 0.117 Uiso 1 1 calc R
H14B H 1.0910 0.8314 0.2321 0.117 Uiso 1 1 calc R
C15 C 0.9431(8) 0.9770(3) 0.24544(11) 0.0859(11) Uani 1 1 d .
H15A H 0.8128 1.0167 0.2344 0.103 Uiso 1 1 calc R
H15B H 1.0790 1.0173 0.2380 0.103 Uiso 1 1 calc R
C16 C 0.9257(6) 0.9652(3) 0.29589(9) 0.0640(7) Uani 1 1 d .
H16A H 1.0639 0.9325 0.3071 0.077 Uiso 1 1 calc R
H16B H 0.9122 1.0360 0.3092 0.077 Uiso 1 1 calc R
C17 C 0.5672(4) 1.02923(18) 0.46951(8) 0.0406(5) Uani 1 1 d .
C18 C 0.7718(4) 1.0206(2) 0.49186(8) 0.0513(6) Uani 1 1 d .
H18 H 0.8835 0.9749 0.4809 0.062 Uiso 1 1 calc R
C19 C 0.8132(5) 1.0788(2) 0.53028(8) 0.0541(6) Uani 1 1 d .
H19 H 0.9511 1.0719 0.5451 0.065 Uiso 1 1 calc R
C20 C 0.6489(5) 1.1469(2) 0.54627(8) 0.0500(7) Uani 1 1 d .
C21 C 0.4452(5) 1.1577(2) 0.52500(8) 0.0524(6) Uani 1 1 d .
H21 H 0.3351 1.2042 0.5360 0.063 Uiso 1 1 calc R
C22 C 0.4045(5) 1.09841(19) 0.48674(8) 0.0468(6) Uani 1 1 d .
H22 H 0.2654 1.1051 0.4723 0.056 Uiso 1 1 calc R
C23 C 0.3469(5) 0.7917(2) 0.45604(9) 0.0530(6) Uani 1 1 d .
H23 H 0.3636 0.7132 0.4589 0.064 Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1163(3) 0.05657(17) 0.04497(15) -0.00971(12) 0.00591(15) -0.02695(16)
O1 0.0362(9) 0.0515(10) 0.0610(10) -0.0050(8) -0.0142(8) 0.0052(9)
O2 0.0663(13) 0.0765(14) 0.132(2) 0.0005(14) 0.0482(15) 0.0020(13)
O3 0.115(2) 0.0513(13) 0.171(3) 0.0344(15) 0.029(2) -0.0037(15)
O4 0.0957(18) 0.0616(13) 0.0771(14) 0.0022(11) -0.0316(13) 0.0199(12)
N1 0.0599(14) 0.0475(13) 0.0593(13) -0.0036(10) -0.0027(11) -0.0038(11)
N2 0.0777(18) 0.0414(13) 0.0592(14) 0.0002(10) 0.0087(14) 0.0058(12)
C1 0.0333(12) 0.0420(12) 0.0376(11) -0.0014(9) -0.0045(9) 0.0038(10)
C2 0.0365(12) 0.0434(12) 0.0392(12) 0.0002(10) -0.0009(10) 0.0035(10)
C3 0.0368(13) 0.0454(13) 0.0414(13) -0.0039(10) -0.0056(10) 0.0050(10)
C4 0.0463(13) 0.0411(12) 0.0410(12) -0.0013(9) -0.0057(11) 0.0012(11)
C5 0.0397(12) 0.0423(12) 0.0361(10) -0.0010(9) -0.0028(10) 0.0058(11)
C6 0.0403(12) 0.0402(12) 0.0394(12) -0.0020(10) 0.0024(10) 0.0003(10)
C7 0.0418(13) 0.0497(13) 0.0609(16) 0.0061(12) -0.0061(13) 0.0001(11)
C8 0.0558(17) 0.0636(18) 0.089(2) 0.0250(17) 0.0113(16) 0.0157(15)
C9 0.084(2) 0.0433(14) 0.0779(19) 0.0060(14) 0.0305(18) 0.0157(17)
C10 0.084(2) 0.0466(15) 0.0607(18) -0.0088(13) 0.0058(15) -0.0129(15)
C11 0.0556(16) 0.0517(14) 0.0356(11) 0.0014(10) -0.0048(11) 0.0043(13)
C12 0.097(2) 0.0590(17) 0.0402(12) -0.0068(11) 0.0062(14) -0.0013(16)
C13 0.142(3) 0.083(2) 0.0402(14) -0.0105(14) 0.0045(19) -0.009(2)
C14 0.129(3) 0.117(3) 0.0453(17) -0.0014(19) 0.028(2) -0.008(3)
C15 0.110(3) 0.096(3) 0.0517(18) 0.0109(17) 0.0131(19) -0.022(2)
C16 0.0751(19) 0.0706(19) 0.0462(15) 0.0027(14) 0.0037(14) -0.0069(16)
C17 0.0428(13) 0.0390(12) 0.0400(12) -0.0003(10) 0.0014(10) 0.0013(11)
C18 0.0446(14) 0.0578(14) 0.0514(13) -0.0094(12) 0.0018(12) 0.0039(12)
C19 0.0492(14) 0.0670(16) 0.0462(13) -0.0011(12) -0.0063(13) -0.0101(14)
C20 0.0743(19) 0.0417(12) 0.0340(11) -0.0011(10) 0.0060(12) -0.0147(12)
C21 0.0695(18) 0.0395(13) 0.0481(14) -0.0023(11) 0.0113(13) 0.0057(13)
C22 0.0522(14) 0.0441(13) 0.0440(13) 0.0028(11) -0.0014(11) 0.0081(11)
C23 0.0542(17) 0.0505(15) 0.0543(14) -0.0027(12) 0.0081(12) -0.0022(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 105(3)
C6 N1 C10 118.1(3)
O4 N2 O3 123.9(3)
O4 N2 C4 119.0(2)
O3 N2 C4 117.1(3)
O1 C1 C6 109.21(19)
O1 C1 C5 111.11(19)
C6 C1 C5 115.30(19)
O1 C1 C2 107.92(19)
C6 C1 C2 110.74(19)
C5 C1 C2 102.17(18)
C23 C2 C3 115.4(2)
C23 C2 C1 111.5(2)
C3 C2 C1 103.15(19)
C23 C2 H2 108.8
C3 C2 H2 108.8
C1 C2 H2 108.8
C17 C3 C2 115.9(2)
C17 C3 C4 114.7(2)
C2 C3 C4 103.52(18)
C17 C3 H3 110.1(12)
C2 C3 H3 104.9(13)
C4 C3 H3 106.8(12)
N2 C4 C3 108.6(2)
N2 C4 C5 113.88(18)
C3 C4 C5 106.90(18)
N2 C4 H4 109.1
C3 C4 H4 109.1
C5 C4 H4 109.1
C1 C5 C11 118.5(2)
C1 C5 C4 104.83(18)
C11 C5 C4 116.81(19)
C1 C5 H5 105.1
C11 C5 H5 105.1
C4 C5 H5 105.1
N1 C6 C7 122.8(2)
N1 C6 C1 116.0(2)
C7 C6 C1 121.1(2)
C6 C7 C8 118.1(3)
C6 C7 H7 120.9
C8 C7 H7 120.9
C9 C8 C7 120.0(3)
C9 C8 H8 120.0
C7 C8 H8 120.0
C10 C9 C8 118.8(3)
C10 C9 H9 120.6
C8 C9 H9 120.6
N1 C10 C9 122.2(3)
N1 C10 H10 118.9
C9 C10 H10 118.9
C16 C11 C12 109.4(2)
C16 C11 C5 110.4(2)
C12 C11 C5 112.6(2)
C16 C11 H11 110.8(14)
C12 C11 H11 105.2(14)
C5 C11 H11 108.4(14)
C11 C12 C13 111.6(2)
C11 C12 H12A 109.3
C13 C12 H12A 109.3
C11 C12 H12B 109.3
C13 C12 H12B 109.3
H12A C12 H12B 108.0
C14 C13 C12 110.7(3)
C14 C13 H13A 109.5
C12 C13 H13A 109.5
C14 C13 H13B 109.5
C12 C13 H13B 109.5
H13A C13 H13B 108.1
C13 C14 C15 111.7(3)
C13 C14 H14A 109.3
C15 C14 H14A 109.3
C13 C14 H14B 109.3
C15 C14 H14B 109.3
H14A C14 H14B 107.9
C14 C15 C16 110.5(3)
C14 C15 H15A 109.5
C16 C15 H15A 109.5
C14 C15 H15B 109.5
C16 C15 H15B 109.5
H15A C15 H15B 108.1
C11 C16 C15 112.3(3)
C11 C16 H16A 109.2
C15 C16 H16A 109.2
C11 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
C18 C17 C22 117.9(2)
C18 C17 C3 122.1(2)
C22 C17 C3 120.0(2)
C17 C18 C19 121.2(2)
C17 C18 H18 119.4
C19 C18 H18 119.4
C20 C19 C18 119.4(2)
C20 C19 H19 120.3
C18 C19 H19 120.3
C21 C20 C19 121.1(2)
C21 C20 Br1 119.3(2)
C19 C20 Br1 119.7(2)
C20 C21 C22 119.2(3)
C20 C21 H21 120.4
C22 C21 H21 120.4
C21 C22 C17 121.3(3)
C21 C22 H22 119.3
C17 C22 H22 119.3
O2 C23 C2 126.0(3)
O2 C23 H23 119.9
C2 C23 H23 114.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C20 1.898(2)
O1 C1 1.421(3)
O1 H1 0.89(4)
O2 C23 1.179(3)
O3 N2 1.208(3)
O4 N2 1.198(3)
N1 C6 1.334(3)
N1 C10 1.348(4)
N2 C4 1.513(3)
C1 C6 1.530(3)
C1 C5 1.540(3)
C1 C2 1.559(3)
C2 C23 1.492(4)
C2 C3 1.526(3)
C2 H2 0.9800
C3 C17 1.509(3)
C3 C4 1.553(3)
C3 H3 0.96(2)
C4 C5 1.560(3)
C4 H4 0.9800
C5 C11 1.543(3)
C5 H5 0.9800
C6 C7 1.360(4)
C7 C8 1.379(4)
C7 H7 0.9300
C8 C9 1.362(5)
C8 H8 0.9300
C9 C10 1.360(5)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.520(4)
C11 C12 1.526(4)
C11 H11 0.95(2)
C12 C13 1.533(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.499(6)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.513(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.525(4)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.383(4)
C17 C22 1.388(3)
C18 C19 1.383(3)
C18 H18 0.9300
C19 C20 1.372(4)
C19 H19 0.9300
C20 C21 1.365(4)
C21 C22 1.386(4)
C21 H21 0.9300
C22 H22 0.9300
C23 H23 0.9856
|
1501989.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501989.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501989
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Dange, Nitin S.'
'Hsu, Che-Sheng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
Dynamic kinetic asymmetric synthesis of five contiguous stereogenic
centers by sequential organocatalytic stetter and Michael-aldol reaction:
enantioselective synthesis of fully substituted cyclopentanols bearing a
quaternary stereocenter.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1338
_journal_page_last 1341
_journal_paper_doi 10.1021/ol200006e
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C24 H30 N2 O5'
_chemical_formula_weight 426.50
_chemical_name_systematic
;
?
;
_space_group_IT_number 20
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'C 2c 2'
_symmetry_space_group_name_H-M 'C 2 2 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 5.6207(4)
_cell_length_b 21.3127(15)
_cell_length_c 37.844(3)
_cell_measurement_reflns_used 7502
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 25.00
_cell_measurement_theta_min 1.08
_cell_volume 4533.4(6)
_computing_cell_refinement DENZO-SMN
_computing_data_collection 'NONIUS COLLECT'
_computing_data_reduction DENZO-SMN
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type 'NONIUS KappaCCD'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0502
_diffrn_reflns_av_sigmaI/netI 0.0726
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 44
_diffrn_reflns_limit_l_min -43
_diffrn_reflns_number 7502
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 1.08
_exptl_absorpt_coefficient_mu 0.088
_exptl_absorpt_correction_T_max 0.992
_exptl_absorpt_correction_T_min 0.932
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.250
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1824
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.655
_refine_diff_density_min -0.348
_refine_diff_density_rms 0.106
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 1(3)
_refine_ls_extinction_coef 0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.055
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 276
_refine_ls_number_reflns 3853
_refine_ls_number_restraints 10
_refine_ls_restrained_S_all 1.067
_refine_ls_R_factor_all 0.1108
_refine_ls_R_factor_gt 0.0732
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1391P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1914
_refine_ls_wR_factor_ref 0.2187
_reflns_number_gt 2616
_reflns_number_total 3853
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200006e_si_004.cif
_cod_data_source_block ic14536
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M C222(1)
_cod_database_code 1501989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2144(5) 1.01387(14) 0.63842(8) 0.0508(8) Uani 1 1 d . . .
H1 H 0.1614 1.0473 0.6471 0.076 Uiso 1 1 calc R . .
O2 O 0.0251(5) 1.01537(14) 0.55789(8) 0.0603(9) Uani 1 1 d . . .
O3 O 0.4648(6) 0.80687(13) 0.45287(8) 0.0564(9) Uani 1 1 d . . .
O4 O 0.3203(12) 0.8592(3) 0.64286(16) 0.0774(17) Uiso 0.63 1 d P A 1
O5 O 0.6409(15) 0.8178(3) 0.63011(18) 0.0898(19) Uiso 0.63 1 d P A 1
O4' O 0.455(3) 0.8344(7) 0.6275(4) 0.099(4) Uiso 0.38 1 d P B 2
O5' O 0.826(2) 0.8374(5) 0.6273(3) 0.084(3) Uiso 0.38 1 d P B 2
N1 N 0.3495(6) 1.12551(16) 0.64902(11) 0.0531(10) Uani 1 1 d . . .
N2 N 0.5073(17) 0.8621(4) 0.6303(2) 0.065(2) Uiso 0.63 1 d P A 1
N2' N 0.638(2) 0.8643(6) 0.6197(3) 0.063(3) Uiso 0.38 1 d P B 2
C1 C 0.4394(6) 1.02568(17) 0.62215(11) 0.0419(10) Uani 1 1 d . . .
C2 C 0.4160(7) 1.00963(18) 0.58264(11) 0.0429(10) Uani 1 1 d . . .
H2 H 0.5623 1.0238 0.5699 0.052 Uiso 1 1 calc R . .
C3 C 0.4084(8) 0.93786(18) 0.58334(12) 0.0461(11) Uani 1 1 d . A .
H3 H 0.2543 0.9257 0.5946 0.055 Uiso 1 1 calc R . .
C4 C 0.6033(10) 0.92204(19) 0.60943(13) 0.0593(13) Uani 1 1 d . . .
H4A H 0.7573 0.9130 0.5972 0.071 Uiso 0.63 1 calc PR A 1
H4B H 0.7474 0.9287 0.5944 0.071 Uiso 0.38 1 calc PR A 2
C5 C 0.6267(8) 0.97816(19) 0.63551(12) 0.0483(11) Uani 1 1 d . A .
H5 H 0.7868 0.9974 0.6315 0.058 Uiso 1 1 calc R . .
C6 C 0.5069(7) 1.09368(17) 0.62980(11) 0.0429(10) Uani 1 1 d . . .
C7 C 0.7158(7) 1.1208(2) 0.61819(12) 0.0493(11) Uani 1 1 d . . .
H7 H 0.8257 1.0975 0.6044 0.059 Uiso 1 1 calc R . .
C8 C 0.7625(9) 1.1828(2) 0.62708(12) 0.0559(12) Uani 1 1 d . . .
H8 H 0.9063 1.2022 0.6197 0.067 Uiso 1 1 calc R . .
C9 C 0.6017(10) 1.2153(2) 0.64632(13) 0.0594(13) Uani 1 1 d . . .
H9 H 0.6300 1.2579 0.6524 0.071 Uiso 1 1 calc R . .
C10 C 0.3960(9) 1.1857(2) 0.65696(14) 0.0591(13) Uani 1 1 d . . .
H10 H 0.2830 1.2086 0.6704 0.071 Uiso 1 1 calc R . .
C11 C 0.2063(8) 1.0405(2) 0.56721(11) 0.0483(11) Uani 1 1 d . . .
H11 H 0.2147 1.0847 0.5643 0.058 Uiso 1 1 calc R . .
C12 C 0.4220(7) 0.90384(18) 0.54847(11) 0.0452(10) Uani 1 1 d . . .
C13 C 0.6022(8) 0.91408(19) 0.52427(12) 0.0491(11) Uani 1 1 d . A .
H13 H 0.7208 0.9445 0.5294 0.059 Uiso 1 1 calc R . .
C14 C 0.6142(8) 0.8812(2) 0.49291(12) 0.0489(11) Uani 1 1 d . . .
H14 H 0.7403 0.8891 0.4768 0.059 Uiso 1 1 calc R A .
C15 C 0.4406(8) 0.83636(18) 0.48486(11) 0.0461(11) Uani 1 1 d . A .
C16 C 0.2617(8) 0.8244(2) 0.50846(12) 0.0511(11) Uani 1 1 d . . .
H16 H 0.1449 0.7934 0.5034 0.061 Uiso 1 1 calc R A .
C17 C 0.2533(8) 0.85856(19) 0.54029(12) 0.0518(11) Uani 1 1 d . A .
H17 H 0.1286 0.8504 0.5566 0.062 Uiso 1 1 calc R . .
C18 C 0.2829(9) 0.7651(2) 0.44258(13) 0.0632(13) Uani 1 1 d . . .
H18A H 0.2623 0.7329 0.4608 0.095 Uiso 1 1 calc R . .
H18B H 0.3262 0.7451 0.4202 0.095 Uiso 1 1 calc R . .
H18C H 0.1337 0.7883 0.4396 0.095 Uiso 1 1 calc R . .
C19 C 0.6091(10) 0.9623(2) 0.67458(12) 0.0626(13) Uani 1 1 d D . .
H19A H 0.4578 0.9391 0.6775 0.075 Uiso 0.50 1 calc PR A -1
H19B H 0.7380 0.9318 0.6793 0.075 Uiso 0.50 1 calc PR A -1
H19C H 0.5878 1.0016 0.6881 0.075 Uiso 0.50 1 calc PR A -2
H19D H 0.4665 0.9360 0.6785 0.075 Uiso 0.50 1 calc PR A -2
C20 C 0.617(2) 1.0058(6) 0.7023(3) 0.092(4) Uiso 0.50 1 d PD A -1
H20A H 0.5795 0.9839 0.7246 0.111 Uiso 0.50 1 calc PR A -1
H20B H 0.4926 1.0379 0.6983 0.111 Uiso 0.50 1 calc PR A -1
C21 C 0.838(3) 1.0362(6) 0.7059(3) 0.097(4) Uiso 0.50 1 d PD A -1
H21A H 0.8573 1.0671 0.6866 0.116 Uiso 0.50 1 calc PR A -1
H21B H 0.9675 1.0048 0.7037 0.116 Uiso 0.50 1 calc PR A -1
C22 C 0.863(3) 1.0710(6) 0.7428(3) 0.091(4) Uiso 0.50 1 d PD A -1
H22A H 0.7352 1.1028 0.7452 0.109 Uiso 0.50 1 calc PR A -1
H22B H 0.8448 1.0404 0.7623 0.109 Uiso 0.50 1 calc PR A -1
C23 C 1.102(2) 1.1023(7) 0.7453(4) 0.100(4) Uiso 0.50 1 d PD A -1
H23A H 1.1244 1.1284 0.7239 0.120 Uiso 0.50 1 calc PR A -1
H23B H 1.2258 1.0693 0.7450 0.120 Uiso 0.50 1 calc PR A -1
C24 C 1.142(3) 1.1435(6) 0.7777(3) 0.106(4) Uiso 0.50 1 d PD A -1
H24A H 1.3043 1.1601 0.7773 0.160 Uiso 0.50 1 calc PR A -1
H24B H 1.1180 1.1186 0.7991 0.160 Uiso 0.50 1 calc PR A -1
H24C H 1.0282 1.1785 0.7774 0.160 Uiso 0.50 1 calc PR A -1
C20' C 0.819(3) 0.9290(8) 0.6882(4) 0.129(4) Uiso 0.50 1 d PD A -2
H20C H 0.9580 0.9576 0.6871 0.155 Uiso 0.50 1 calc PR A -2
H20D H 0.8534 0.8929 0.6725 0.155 Uiso 0.50 1 calc PR A -2
C21' C 0.794(2) 0.9051(5) 0.7259(3) 0.079(3) Uiso 0.50 1 d PD A -2
H21C H 0.6553 0.8765 0.7271 0.095 Uiso 0.50 1 calc PR A -2
H21D H 0.7619 0.9411 0.7417 0.095 Uiso 0.50 1 calc PR A -2
C22' C 1.014(3) 0.8705(7) 0.7390(3) 0.111(5) Uiso 0.50 1 d PD A -2
H22C H 1.0826 0.8485 0.7184 0.133 Uiso 0.50 1 calc PR A -2
H22D H 1.1301 0.9029 0.7462 0.133 Uiso 0.50 1 calc PR A -2
C23' C 1.002(3) 0.8236(7) 0.7685(4) 0.122(5) Uiso 0.50 1 d PD A -2
H23C H 0.8405 0.8072 0.7731 0.146 Uiso 0.50 1 calc PR A -2
H23D H 1.0799 0.8377 0.7906 0.146 Uiso 0.50 1 calc PR A -2
C24' C 1.164(3) 0.7786(7) 0.7446(5) 0.129(4) Uiso 0.50 1 d PD A -2
H24D H 1.1930 0.7392 0.7573 0.193 Uiso 0.50 1 calc PR A -2
H24E H 1.3156 0.7993 0.7396 0.193 Uiso 0.50 1 calc PR A -2
H24F H 1.0811 0.7696 0.7224 0.193 Uiso 0.50 1 calc PR A -2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0366(15) 0.0473(16) 0.068(2) -0.0040(15) 0.0056(14) -0.0015(13)
O2 0.0414(17) 0.0598(18) 0.080(2) -0.0068(17) -0.0114(15) -0.0028(16)
O3 0.065(2) 0.0511(17) 0.0531(18) -0.0049(15) 0.0007(16) -0.0016(16)
N1 0.047(2) 0.043(2) 0.069(2) -0.0055(18) -0.0010(19) 0.0042(17)
C1 0.028(2) 0.041(2) 0.057(2) -0.004(2) 0.0021(18) -0.0038(17)
C2 0.033(2) 0.036(2) 0.059(3) -0.0005(19) 0.0003(19) -0.0033(17)
C3 0.038(2) 0.039(2) 0.061(3) -0.007(2) -0.002(2) -0.0048(18)
C4 0.072(3) 0.039(2) 0.067(3) -0.006(2) -0.012(3) 0.015(2)
C5 0.042(2) 0.040(2) 0.063(3) -0.001(2) -0.001(2) 0.0008(19)
C6 0.039(2) 0.038(2) 0.052(2) -0.0008(19) -0.007(2) -0.0033(18)
C7 0.040(2) 0.049(2) 0.059(3) 0.001(2) 0.001(2) -0.004(2)
C8 0.055(3) 0.048(2) 0.064(3) 0.001(2) 0.000(2) -0.010(2)
C9 0.075(3) 0.035(2) 0.068(3) -0.001(2) -0.014(3) -0.010(2)
C10 0.061(3) 0.040(2) 0.076(3) -0.015(2) -0.003(3) 0.008(2)
C11 0.042(2) 0.049(2) 0.054(3) -0.002(2) 0.001(2) -0.003(2)
C12 0.040(2) 0.038(2) 0.057(3) 0.002(2) 0.001(2) -0.0026(19)
C13 0.043(2) 0.039(2) 0.065(3) -0.004(2) -0.003(2) -0.0055(19)
C14 0.044(2) 0.044(2) 0.059(3) 0.005(2) -0.002(2) -0.001(2)
C15 0.050(3) 0.038(2) 0.051(2) -0.0016(19) -0.002(2) 0.000(2)
C16 0.051(3) 0.044(2) 0.059(3) -0.012(2) 0.000(2) -0.006(2)
C17 0.042(2) 0.048(2) 0.066(3) -0.006(2) 0.007(2) -0.005(2)
C18 0.071(3) 0.058(3) 0.061(3) -0.006(2) -0.011(3) 0.002(3)
C19 0.065(3) 0.069(3) 0.054(3) 0.002(2) -0.004(2) 0.015(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 O3 C18 117.5(4)
C6 N1 C10 118.7(4)
O4 N2 O5 121.8(10)
O4 N2 C4 123.7(7)
O5 N2 C4 114.3(9)
O5' N2' O4' 114.3(12)
O5' N2' C4 129.4(12)
O4' N2' C4 115.5(13)
O1 C1 C6 107.8(3)
O1 C1 C2 107.7(3)
C6 C1 C2 114.6(3)
O1 C1 C5 110.3(3)
C6 C1 C5 113.0(3)
C2 C1 C5 103.3(3)
C11 C2 C3 115.6(4)
C11 C2 C1 110.8(3)
C3 C2 C1 102.0(3)
C12 C3 C4 115.3(4)
C12 C3 C2 117.7(4)
C4 C3 C2 102.3(3)
N2' C4 C3 120.8(7)
N2' C4 C5 121.5(6)
C3 C4 C5 107.7(3)
N2' C4 N2 31.6(6)
C3 C4 N2 104.9(5)
C5 C4 N2 109.2(4)
C19 C5 C1 114.8(4)
C19 C5 C4 116.1(4)
C1 C5 C4 103.8(3)
N1 C6 C7 121.7(4)
N1 C6 C1 115.0(3)
C7 C6 C1 123.3(4)
C6 C7 C8 118.8(4)
C9 C8 C7 119.5(5)
C8 C9 C10 118.9(4)
N1 C10 C9 122.4(4)
O2 C11 C2 126.5(4)
C13 C12 C17 117.5(4)
C13 C12 C3 122.7(4)
C17 C12 C3 119.7(4)
C14 C13 C12 121.7(4)
C13 C14 C15 120.0(4)
C16 C15 O3 124.3(4)
C16 C15 C14 119.8(4)
O3 C15 C14 115.9(4)
C15 C16 C17 119.1(4)
C12 C17 C16 121.8(4)
C20 C19 C20' 91.8(9)
C20 C19 C5 125.4(7)
C20' C19 C5 113.3(7)
C19 C20 C21 114.0(10)
C20 C21 C22 112.1(11)
C23 C22 C21 109.7(10)
C22 C23 C24 115.8(11)
C19 C20' C21' 114.5(11)
C20' C21' C22' 113.1(11)
C23' C22' C21' 122.1(12)
C22' C23' C24' 87.5(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.429(5)
O2 C11 1.204(5)
O3 C15 1.371(5)
O3 C18 1.410(5)
O4 N2 1.155(11)
O5 N2 1.207(11)
O4' N2' 1.24(2)
O5' N2' 1.235(15)
N1 C6 1.331(5)
N1 C10 1.342(6)
N2 C4 1.596(11)
N2' C4 1.305(13)
C1 C6 1.526(5)
C1 C2 1.539(6)
C1 C5 1.546(6)
C2 C11 1.471(6)
C2 C3 1.530(6)
C3 C12 1.507(6)
C3 C4 1.513(6)
C4 C5 1.556(6)
C5 C19 1.520(7)
C6 C7 1.381(6)
C7 C8 1.388(6)
C8 C9 1.352(7)
C9 C10 1.377(7)
C12 C13 1.383(6)
C12 C17 1.388(6)
C13 C14 1.380(6)
C14 C15 1.400(6)
C15 C16 1.369(6)
C16 C17 1.409(6)
C19 C20 1.399(11)
C19 C20' 1.473(14)
C20 C21 1.409(14)
C21 C22 1.589(14)
C22 C23 1.503(14)
C23 C24 1.526(14)
C20' C21' 1.521(15)
C21' C22' 1.521(15)
C22' C23' 1.498(13)
C23' C24' 1.601(15)
|
1501990.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501990.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501990
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Dange, Nitin S.'
'Hsu, Che-Sheng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
Dynamic kinetic asymmetric synthesis of five contiguous stereogenic
centers by sequential organocatalytic stetter and Michael-aldol reaction:
enantioselective synthesis of fully substituted cyclopentanols bearing a
quaternary stereocenter.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1338
_journal_page_last 1341
_journal_paper_doi 10.1021/ol200006e
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C10 H10.5 Br0.5 N O2'
_chemical_formula_weight 216.65
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 112.947(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.6085(17)
_cell_length_b 5.7821(8)
_cell_length_c 15.108(2)
_cell_measurement_reflns_used 1628
_cell_measurement_temperature 200(2)
_cell_measurement_theta_max 20.66
_cell_measurement_theta_min 2.69
_cell_volume 1014.3(2)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method 'omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0462
_diffrn_reflns_av_sigmaI/netI 0.0896
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 9996
_diffrn_reflns_theta_full 27.50
_diffrn_reflns_theta_max 27.50
_diffrn_reflns_theta_min 1.46
_exptl_absorpt_coefficient_mu 2.053
_exptl_absorpt_correction_T_max 0.8867
_exptl_absorpt_correction_T_min 0.3722
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.419
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 444
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.693
_refine_diff_density_min -0.501
_refine_diff_density_rms 0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.02(2)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.064
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 234
_refine_ls_number_reflns 4600
_refine_ls_number_restraints 9
_refine_ls_restrained_S_all 1.093
_refine_ls_R_factor_all 0.1166
_refine_ls_R_factor_gt 0.0713
_refine_ls_shift/su_max 0.008
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.2116P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1695
_refine_ls_wR_factor_ref 0.2014
_reflns_number_gt 2844
_reflns_number_total 4600
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200006e_si_005.cif
_cod_data_source_block ic14704
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
The following automatic conversions were performed:
'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.
Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas
;
_cod_original_sg_symbol_H-M P2(1)
_cod_original_formula_sum 'C10 H10.50 Br0.50 N O2'
_cod_database_code 1501990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.59992(9) 0.3915(2) 0.09798(5) 0.1034(4) Uani 1 1 d . . .
O1 O 0.8125(3) -0.1536(7) 0.7096(3) 0.0520(10) Uani 1 1 d . . .
H1 H 0.8030 -0.1810 0.7592 0.078 Uiso 1 1 calc R . .
O2 O 0.5817(4) -0.2571(8) 0.4966(4) 0.0640(13) Uani 1 1 d . . .
O3 O 1.0783(8) 0.0300(17) 0.6083(8) 0.0645(19) Uiso 0.557(9) 1 d P A 1
O4 O 0.9681(9) -0.2482(18) 0.6012(8) 0.069(2) Uiso 0.557(9) 1 d P A 1
O3' O 1.0629(10) 0.092(2) 0.5672(10) 0.0645(19) Uiso 0.443(9) 1 d P A 2
O4' O 0.9880(11) -0.182(2) 0.6341(10) 0.069(2) Uiso 0.443(9) 1 d P A 2
N1 N 0.7184(5) 0.0507(13) 0.8151(4) 0.0692(17) Uani 1 1 d . . .
N2 N 0.9820(11) -0.038(2) 0.6020(9) 0.0507(19) Uiso 0.557(9) 1 d PD A 1
N2' N 0.9851(13) 0.000(3) 0.5853(12) 0.0507(19) Uiso 0.443(9) 1 d PD A 2
C1 C 0.7770(4) 0.0788(10) 0.6794(4) 0.0399(12) Uani 1 1 d . . .
C2 C 0.6948(4) 0.0704(9) 0.5716(3) 0.0327(10) Uani 1 1 d . . .
H2 H 0.6570 0.2212 0.5536 0.039 Uiso 1 1 calc R . .
C3 C 0.7718(4) 0.0335(10) 0.5160(4) 0.0354(11) Uani 1 1 d . A .
H3 H 0.7846 -0.1333 0.5142 0.042 Uiso 1 1 calc R . .
C4 C 0.8887(4) 0.1450(11) 0.5805(4) 0.0470(14) Uani 1 1 d D . .
H4 H 0.9058 0.2786 0.5483 0.056 Uiso 0.557(9) 1 calc PR A 1
H4' H 0.8953 0.2879 0.5481 0.056 Uiso 0.443(9) 1 calc PR A 2
C5 C 0.8784(4) 0.2200(12) 0.6762(4) 0.0487(14) Uani 1 1 d D A .
H5 H 0.8476 0.3776 0.6627 0.058 Uiso 0.557(9) 1 calc PR A 1
H5' H 0.8627 0.3861 0.6757 0.058 Uiso 0.443(9) 1 calc PR A 2
C6 C 0.9904(10) 0.249(2) 0.7640(7) 0.052(2) Uiso 0.557(9) 1 d PD A 1
H6A H 1.0200 0.0968 0.7875 0.062 Uiso 0.557(9) 1 calc PR A 1
H6B H 1.0459 0.3238 0.7434 0.062 Uiso 0.557(9) 1 calc PR A 1
C7 C 0.9841(11) 0.386(3) 0.8469(8) 0.069(3) Uiso 0.557(9) 1 d PD A 1
H7A H 0.9342 0.3072 0.8723 0.083 Uiso 0.557(9) 1 calc PR A 1
H7B H 0.9511 0.5373 0.8241 0.083 Uiso 0.557(9) 1 calc PR A 1
C8 C 1.1027(13) 0.416(4) 0.9260(11) 0.096(4) Uiso 0.557(9) 1 d PD A 1
H8A H 1.0964 0.5041 0.9777 0.144 Uiso 0.557(9) 1 calc PR A 1
H8B H 1.1518 0.4961 0.9011 0.144 Uiso 0.557(9) 1 calc PR A 1
H8C H 1.1348 0.2669 0.9494 0.144 Uiso 0.557(9) 1 calc PR A 1
C6' C 0.9888(12) 0.157(3) 0.7616(9) 0.052(2) Uiso 0.443(9) 1 d PD A 2
H6'A H 0.9934 -0.0097 0.7685 0.062 Uiso 0.443(9) 1 calc PR A 2
H6'B H 1.0544 0.2079 0.7483 0.062 Uiso 0.443(9) 1 calc PR A 2
C7' C 0.9968(15) 0.263(4) 0.8553(11) 0.069(3) Uiso 0.443(9) 1 d PD A 2
H7'A H 0.9391 0.1893 0.8735 0.083 Uiso 0.443(9) 1 calc PR A 2
H7'B H 0.9759 0.4248 0.8436 0.083 Uiso 0.443(9) 1 calc PR A 2
C8' C 1.1116(17) 0.249(5) 0.9412(15) 0.096(4) Uiso 0.443(9) 1 d PD A 2
H8'A H 1.1048 0.3241 0.9955 0.144 Uiso 0.443(9) 1 calc PR A 2
H8'B H 1.1699 0.3253 0.9258 0.144 Uiso 0.443(9) 1 calc PR A 2
H8'C H 1.1324 0.0902 0.9565 0.144 Uiso 0.443(9) 1 calc PR A 2
C9 C 0.7192(4) 0.1807(10) 0.7416(4) 0.0409(12) Uani 1 1 d . . .
C10 C 0.6664(5) 0.3867(13) 0.7208(4) 0.0511(13) Uani 1 1 d . . .
H10 H 0.6673 0.4711 0.6687 0.061 Uiso 1 1 calc R . .
C11 C 0.6105(7) 0.4749(13) 0.7766(6) 0.073(2) Uani 1 1 d . . .
H11 H 0.5741 0.6181 0.7625 0.088 Uiso 1 1 calc R . .
C12 C 0.6099(6) 0.3471(19) 0.8527(4) 0.075(2) Uani 1 1 d . . .
H12 H 0.5727 0.4003 0.8912 0.090 Uiso 1 1 calc R . .
C13 C 0.6657(7) 0.1385(17) 0.8704(5) 0.082(3) Uani 1 1 d . . .
H13 H 0.6676 0.0530 0.9231 0.098 Uiso 1 1 calc R . .
C14 C 0.6042(4) -0.1093(12) 0.5554(3) 0.0392(11) Uani 1 1 d . . .
H14 H 0.5624 -0.1049 0.5943 0.047 Uiso 1 1 calc R . .
C15 C 0.7256(4) 0.1204(10) 0.4137(4) 0.0373(12) Uani 1 1 d . . .
C16 C 0.6727(5) 0.3357(10) 0.3883(4) 0.0437(14) Uani 1 1 d . A .
H16 H 0.6633 0.4278 0.4352 0.052 Uiso 1 1 calc R . .
C17 C 0.6339(5) 0.4148(12) 0.2948(4) 0.0517(14) Uani 1 1 d . . .
H17 H 0.5977 0.5578 0.2782 0.062 Uiso 1 1 calc R A .
C18 C 0.6498(6) 0.2776(13) 0.2265(4) 0.0575(17) Uani 1 1 d . A .
C19 C 0.7028(6) 0.0688(14) 0.2488(5) 0.0620(17) Uani 1 1 d . . .
H19 H 0.7143 -0.0204 0.2020 0.074 Uiso 1 1 calc R A .
C20 C 0.7391(5) -0.0076(11) 0.3422(4) 0.0516(15) Uani 1 1 d . A .
H20 H 0.7743 -0.1517 0.3576 0.062 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br 0.1324(8) 0.1382(8) 0.0465(4) 0.0193(5) 0.0423(4) 0.0245(7)
O1 0.046(2) 0.050(2) 0.058(2) 0.016(2) 0.0189(18) 0.008(2)
O2 0.050(2) 0.061(3) 0.097(4) -0.025(3) 0.046(2) -0.019(2)
N1 0.060(3) 0.096(4) 0.057(3) 0.027(3) 0.028(3) 0.017(3)
C1 0.033(3) 0.045(3) 0.040(3) 0.009(2) 0.013(2) 0.003(3)
C2 0.028(2) 0.033(3) 0.039(2) 0.003(2) 0.0155(19) 0.003(2)
C3 0.022(2) 0.040(3) 0.046(3) 0.000(2) 0.016(2) -0.001(2)
C4 0.022(2) 0.069(4) 0.050(3) 0.001(3) 0.014(2) 0.000(3)
C5 0.024(3) 0.069(4) 0.048(3) -0.007(3) 0.009(2) -0.008(3)
C9 0.032(3) 0.052(3) 0.035(3) 0.002(2) 0.009(2) -0.003(3)
C10 0.059(3) 0.053(3) 0.056(3) 0.006(3) 0.039(3) 0.003(3)
C11 0.076(5) 0.068(5) 0.089(5) -0.010(4) 0.049(4) 0.000(4)
C12 0.060(4) 0.129(8) 0.046(3) -0.015(5) 0.032(3) 0.001(5)
C13 0.069(5) 0.126(8) 0.056(4) 0.043(4) 0.029(3) 0.026(5)
C14 0.023(2) 0.047(3) 0.047(2) -0.007(3) 0.0131(19) -0.006(3)
C15 0.026(2) 0.047(3) 0.044(3) -0.005(2) 0.018(2) -0.004(2)
C16 0.041(3) 0.052(4) 0.046(3) -0.009(3) 0.026(2) -0.006(3)
C17 0.054(3) 0.055(4) 0.048(3) 0.009(3) 0.021(2) 0.004(3)
C18 0.057(4) 0.080(5) 0.040(3) 0.006(3) 0.025(3) -0.007(4)
C19 0.067(4) 0.078(5) 0.053(4) -0.016(4) 0.037(3) -0.002(4)
C20 0.047(3) 0.055(4) 0.060(4) -0.010(3) 0.029(3) 0.005(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C13 117.7(7)
O4 N2 O3 116.4(11)
O4 N2 C4 126.3(11)
O3 N2 C4 116.6(10)
O3' N2' O4' 129.4(13)
O3' N2' C4 117.3(12)
O4' N2' C4 109.8(12)
O1 C1 C9 109.5(4)
O1 C1 C5 110.4(4)
C9 C1 C5 114.9(5)
O1 C1 C2 107.6(5)
C9 C1 C2 112.1(4)
C5 C1 C2 102.0(4)
C14 C2 C3 115.0(4)
C14 C2 C1 110.4(4)
C3 C2 C1 105.8(4)
C15 C3 C2 116.2(4)
C15 C3 C4 113.4(4)
C2 C3 C4 104.4(4)
N2' C4 N2 13.1(9)
N2' C4 C3 111.2(8)
N2 C4 C3 108.1(7)
N2' C4 C5 118.9(8)
N2 C4 C5 109.4(6)
C3 C4 C5 107.1(4)
C6 C5 C6' 20.2(7)
C6 C5 C1 122.2(7)
C6' C5 C1 110.1(8)
C6 C5 C4 116.9(6)
C6' C5 C4 109.8(7)
C1 C5 C4 104.6(5)
C7 C6 C5 116.7(10)
C6 C7 C8 111.0(12)
C7' C6' C5 113.7(12)
C6' C7' C8' 118.2(16)
C10 C9 N1 121.9(5)
C10 C9 C1 121.0(5)
N1 C9 C1 117.1(5)
C9 C10 C11 120.4(6)
C12 C11 C10 118.8(8)
C13 C12 C11 118.0(6)
N1 C13 C12 123.2(6)
O2 C14 C2 124.7(5)
C20 C15 C16 117.2(5)
C20 C15 C3 120.6(5)
C16 C15 C3 122.1(5)
C17 C16 C15 121.2(5)
C18 C17 C16 118.6(6)
C19 C18 C17 121.9(6)
C19 C18 Br 119.6(5)
C17 C18 Br 118.5(5)
C18 C19 C20 118.3(6)
C15 C20 C19 122.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C18 1.910(6)
O1 C1 1.434(7)
O2 C14 1.185(7)
O3 N2 1.244(16)
O4 N2 1.229(16)
O3' N2' 1.237(18)
O4' N2' 1.27(2)
N1 C9 1.343(7)
N1 C13 1.353(10)
N2 C4 1.519(12)
N2' C4 1.455(14)
C1 C9 1.515(8)
C1 C5 1.533(8)
C1 C2 1.554(7)
C2 C14 1.492(8)
C2 C3 1.526(7)
C3 C15 1.510(7)
C3 C4 1.555(7)
C4 C5 1.563(8)
C5 C6 1.524(11)
C5 C6' 1.528(13)
C6 C7 1.510(14)
C7 C8 1.517(15)
C6' C7' 1.509(16)
C7' C8' 1.523(17)
C9 C10 1.341(9)
C10 C11 1.390(9)
C11 C12 1.369(11)
C12 C13 1.369(13)
C15 C20 1.374(8)
C15 C16 1.394(8)
C16 C17 1.381(7)
C17 C18 1.376(9)
C18 C19 1.357(10)
C19 C20 1.376(9)
|
1501991.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501991.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501991
loop_
_publ_author_name
'Gessner, Viktoria H.'
'Tilley, T. Don'
_publ_section_title
;
Diphenylanthracene macrocylces from reductive zirconocene coupling: on
the edge of steric overload.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1154
_journal_page_last 1157
_journal_paper_doi 10.1021/ol2000099
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C36 H34 Si2'
_chemical_formula_weight 522.81
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_date 2010-11-26T11:01:16-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 90
_cell_angle_beta 104.004(5)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 17.8049(8)
_cell_length_b 8.5396(3)
_cell_length_c 10.2930(5)
_cell_measurement_temperature 173(2)
_cell_volume 1518.50(12)
_computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0428
_diffrn_reflns_av_unetI/netI 0.0428
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 18556
_diffrn_reflns_theta_full 25
_diffrn_reflns_theta_max 25
_diffrn_reflns_theta_min 2.36
_exptl_absorpt_coefficient_mu 0.139
_exptl_absorpt_correction_T_max 0.9872
_exptl_absorpt_correction_T_min 0.9025
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn 1.143
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 556
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.4
_exptl_crystal_size_min 0.1
_refine_diff_density_max 0.181
_refine_diff_density_min -0.263
_refine_diff_density_rms 0.036
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.009
_refine_ls_hydrogen_treatment riding
_refine_ls_matrix_type full
_refine_ls_number_parameters 175
_refine_ls_number_reflns 2672
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.009
_refine_ls_R_factor_all 0.0532
_refine_ls_R_factor_gt 0.0352
_refine_ls_shift/su_max 0.042
_refine_ls_shift/su_mean 0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0828
_refine_ls_wR_factor_ref 0.0855
_reflns_number_gt 1969
_reflns_number_total 2672
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000099_si_001.cif
_cod_data_source_block anthra
_cod_original_cell_volume 1518.50(11)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1501991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C3 C -0.00087(11) 1.3304(3) 0.2710(3) 0.0667(8) Uani 1 1 d .
H3A H -0.0298 1.4291 0.2582 0.1 Uiso 1 1 calc R
H3B H -0.0084 1.2778 0.3516 0.1 Uiso 1 1 calc R
H3C H -0.0196 1.2627 0.1931 0.1 Uiso 1 1 calc R
C2 C 0.11974(12) 1.4657(2) 0.1380(2) 0.0478(6) Uani 1 1 d .
H2A H 0.1755 1.4779 0.1471 0.072 Uiso 1 1 calc R
H2B H 0.0949 1.5688 0.1265 0.072 Uiso 1 1 calc R
H2C H 0.0977 1.4004 0.0598 0.072 Uiso 1 1 calc R
C1 C 0.14064(12) 1.4920(2) 0.44128(19) 0.0438(5) Uani 1 1 d .
H1A H 0.1333 1.4362 0.5205 0.066 Uiso 1 1 calc R
H1B H 0.1127 1.5917 0.4324 0.066 Uiso 1 1 calc R
H1C H 0.1959 1.5119 0.4509 0.066 Uiso 1 1 calc R
C7 C 0.25097(9) 0.8136(2) 0.30053(18) 0.0290(4) Uani 1 1 d .
H7 H 0.2068 0.7945 0.2294 0.035 Uiso 1 1 calc R
C5 C 0.20011(9) 1.0756(2) 0.33820(17) 0.0254(4) Uani 1 1 d .
C11 C 0.32136(10) 0.9763(2) 0.47509(18) 0.0325(5) Uani 1 1 d .
H11 H 0.3261 1.071 0.5249 0.039 Uiso 1 1 calc R
C10 C 0.37923(10) 0.8654(2) 0.50685(17) 0.0309(4) Uani 1 1 d .
H10 H 0.4231 0.8845 0.5786 0.037 Uiso 1 1 calc R
C8 C 0.30942(9) 0.7027(2) 0.33206(18) 0.0272(4) Uani 1 1 d .
H8 H 0.3049 0.6085 0.2817 0.033 Uiso 1 1 calc R
C4 C 0.15770(10) 1.1866(2) 0.31490(18) 0.0297(4) Uani 1 1 d .
C16 C 0.63381(9) 0.66325(19) 0.30909(16) 0.0240(4) Uani 1 1 d .
H16 H 0.6777 0.6761 0.273 0.029 Uiso 1 1 calc R
C14 C 0.50985(9) 0.75603(19) 0.32895(15) 0.0208(4) Uani 1 1 d .
H14 H 0.4692 0.8308 0.3071 0.025 Uiso 1 1 calc R
C15 C 0.57245(9) 0.7723(2) 0.27676(15) 0.0231(4) Uani 1 1 d .
H15 H 0.575 0.8572 0.2184 0.028 Uiso 1 1 calc R
C6 C 0.25655(9) 0.9518(2) 0.37199(16) 0.0218(4) Uani 1 1 d .
C9 C 0.37429(9) 0.72695(18) 0.43572(15) 0.0189(4) Uani 1 1 d .
C17 C 0.63077(9) 0.54070(19) 0.39089(16) 0.0208(4) Uani 1 1 d .
H17 H 0.6725 0.4683 0.4107 0.025 Uiso 1 1 calc R
C18 C 0.56600(9) 0.51802(18) 0.44807(15) 0.0172(4) Uani 1 1 d .
C12 C 0.43841(9) 0.60957(18) 0.46833(15) 0.0177(4) Uani 1 1 d .
C13 C 0.50365(9) 0.62941(18) 0.41582(14) 0.0168(3) Uani 1 1 d .
Si1 Si 0.10291(3) 1.37115(6) 0.29036(5) 0.02831(16) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3 0.0265(12) 0.0393(14) 0.129(2) 0.0037(14) 0.0079(13) 0.0057(10)
C2 0.0673(15) 0.0350(13) 0.0398(12) 0.0018(10) 0.0106(11) 0.0126(11)
C1 0.0504(13) 0.0394(12) 0.0397(13) 0.0019(10) 0.0073(10) 0.0101(10)
C7 0.0193(9) 0.0254(10) 0.0372(11) 0.0002(9) -0.0030(8) 0.0018(8)
C5 0.0237(9) 0.0254(10) 0.0282(10) 0.0035(8) 0.0082(8) 0.0018(8)
C11 0.0416(11) 0.0231(10) 0.0285(10) -0.0081(8) 0.0003(9) 0.0139(9)
C10 0.0329(10) 0.0285(10) 0.0245(10) -0.0063(9) -0.0065(8) 0.0105(9)
C8 0.0250(10) 0.0175(9) 0.0358(11) -0.0061(8) 0.0007(8) 0.0018(8)
C4 0.0263(10) 0.0276(10) 0.0354(11) 0.0036(9) 0.0078(8) 0.0057(9)
C16 0.0244(9) 0.0248(10) 0.0246(10) -0.0038(8) 0.0094(8) -0.0037(8)
C14 0.0226(9) 0.0175(9) 0.0194(9) -0.0003(7) -0.0005(7) 0.0022(7)
C15 0.0292(10) 0.0190(10) 0.0201(9) 0.0035(7) 0.0040(8) -0.0005(7)
C6 0.0208(9) 0.0213(9) 0.0247(10) 0.0058(8) 0.0078(8) 0.0050(7)
C9 0.0206(9) 0.0166(9) 0.0197(9) 0.0037(7) 0.0054(7) 0.0021(7)
C17 0.0204(9) 0.0195(9) 0.0219(9) -0.0025(7) 0.0037(7) 0.0016(7)
C18 0.0199(8) 0.0153(9) 0.0146(8) -0.0054(7) 0.0009(7) 0.0008(7)
C12 0.0201(8) 0.0157(9) 0.0156(8) -0.0033(7) 0.0008(7) 0.0017(7)
C13 0.0210(8) 0.0138(8) 0.0136(8) -0.0030(7) 0.0003(7) 0.0004(7)
Si1 0.0231(3) 0.0212(3) 0.0390(3) 0.0022(2) 0.0042(2) 0.0070(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C7 C8 120.37(16) . .
C4 C5 C6 174.82(19) . .
C10 C11 C6 121.01(16) . .
C11 C10 C9 120.91(16) . .
C9 C8 C7 121.14(16) . .
C5 C4 Si1 172.93(17) . .
C17 C16 C15 120.77(15) . .
C15 C14 C13 121.49(15) . .
C14 C15 C16 120.13(15) . .
C7 C6 C11 118.53(15) . .
C7 C6 C5 122.80(15) . .
C11 C6 C5 118.55(16) . .
C10 C9 C8 118.03(15) . .
C10 C9 C12 120.49(14) . .
C8 C9 C12 121.46(14) . .
C16 C17 C18 121.28(15) . .
C12 C18 C17 121.91(14) 3_666 .
C12 C18 C13 120.05(14) 3_666 .
C17 C18 C13 118.03(14) . .
C13 C12 C18 120.27(14) . 3_666
C13 C12 C9 119.35(14) . .
C18 C12 C9 120.37(14) 3_666 .
C12 C13 C14 122.01(14) . .
C12 C13 C18 119.68(14) . .
C14 C13 C18 118.30(14) . .
C4 Si1 C3 109.73(9) . .
C4 Si1 C2 107.52(9) . .
C3 Si1 C2 110.77(11) . .
C4 Si1 C1 106.85(9) . .
C3 Si1 C1 110.28(11) . .
C2 Si1 C1 111.57(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 Si1 1.843(2) .
C2 Si1 1.851(2) .
C1 Si1 1.850(2) .
C7 C6 1.381(2) .
C7 C8 1.386(2) .
C5 C4 1.199(2) .
C5 C6 1.442(2) .
C11 C10 1.379(2) .
C11 C6 1.382(2) .
C10 C9 1.382(2) .
C8 C9 1.385(2) .
C4 Si1 1.8386(19) .
C16 C17 1.352(2) .
C16 C15 1.413(2) .
C14 C15 1.356(2) .
C14 C13 1.424(2) .
C9 C12 1.495(2) .
C17 C18 1.429(2) .
C18 C12 1.402(2) 3_666
C18 C13 1.439(2) .
C12 C13 1.405(2) .
C12 C18 1.402(2) 3_666
|
1501992.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501992.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501992
loop_
_publ_author_name
'Gessner, Viktoria H.'
'Tilley, T. Don'
_publ_section_title
;
Diphenylanthracene macrocylces from reductive zirconocene coupling: on
the edge of steric overload.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1154
_journal_page_last 1157
_journal_paper_doi 10.1021/ol2000099
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C108 H108 Si6'
_chemical_formula_weight 1574.48
_chemical_name_systematic
;
?
;
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_date 2011-01-21T15:41:57-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 90
_cell_angle_beta 104.904(8)
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 78.14(4)
_cell_length_b 11.995(6)
_cell_length_c 25.629(12)
_cell_measurement_temperature 149(2)
_cell_volume 23214(2)
_computing_molecular_graphics 'Ortep-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 149(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker APEX-CCD'
_diffrn_measurement_method omega-scans
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.2994
_diffrn_reflns_av_unetI/netI 0.2509
_diffrn_reflns_limit_h_max 89
_diffrn_reflns_limit_h_min -92
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_number 113515
_diffrn_reflns_theta_full 25
_diffrn_reflns_theta_max 25
_diffrn_reflns_theta_min 1.08
_exptl_absorpt_coefficient_mu 0.109
_exptl_absorpt_correction_T_max 0.9873
_exptl_absorpt_correction_T_min 0.9459
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details 'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 0.901
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 6720
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.4
_exptl_crystal_size_min 0.1
_refine_diff_density_max 0.328
_refine_diff_density_min -0.263
_refine_diff_density_rms 0.092
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.094
_refine_ls_hydrogen_treatment riding
_refine_ls_matrix_type full
_refine_ls_number_parameters 1045
_refine_ls_number_reflns 20381
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.094
_refine_ls_R_factor_all 0.2386
_refine_ls_R_factor_gt 0.1116
_refine_ls_shift/su_max 0.153
_refine_ls_shift/su_mean 0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2185
_refine_ls_wR_factor_ref 0.2345
_reflns_number_gt 4504
_reflns_number_total 20381
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000099_si_001.cif
_cod_data_source_block vg172neu
_cod_original_cell_volume 23215(19)
_cod_original_sg_symbol_H-M C2/c
_cod_database_code 1501992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.10742(12) 0.9630(7) 0.3567(4) 0.185(4) Uani 1 1 d .
H1A H 0.1172 0.9136 0.3746 0.277 Uiso 1 1 calc R
H1B H 0.1081 1.0324 0.3774 0.277 Uiso 1 1 calc R
H1C H 0.1083 0.98 0.3201 0.277 Uiso 1 1 calc R
C2 C 0.08827(13) 0.7382(6) 0.3490(4) 0.190(4) Uani 1 1 d .
H2A H 0.0849 0.703 0.3794 0.284 Uiso 1 1 calc R
H2B H 0.1006 0.7193 0.3506 0.284 Uiso 1 1 calc R
H2C H 0.0806 0.711 0.315 0.284 Uiso 1 1 calc R
C3 C 0.06867(12) 0.9461(8) 0.2886(3) 0.199(5) Uani 1 1 d .
H3A H 0.0744 0.9543 0.259 0.299 Uiso 1 1 calc R
H3B H 0.064 1.0184 0.2962 0.299 Uiso 1 1 calc R
H3C H 0.059 0.8922 0.2784 0.299 Uiso 1 1 calc R
C4 C 0.07547(9) 0.9274(5) 0.4070(3) 0.091(2) Uani 1 1 d .
H4 H 0.0629 0.9251 0.3943 0.109 Uiso 1 1 calc R
C5 C 0.08059(11) 0.9553(5) 0.4608(3) 0.063(2) Uani 1 1 d .
C6 C 0.06782(11) 0.9880(6) 0.4926(3) 0.067(2) Uani 1 1 d .
C7 C 0.05385(9) 1.0576(5) 0.4699(3) 0.073(2) Uani 1 1 d .
H7 H 0.0548 1.0917 0.4373 0.088 Uiso 1 1 calc R
C8 C 0.02512(8) 0.9850(6) 0.5284(3) 0.135(3) Uani 1 1 d .
H8A H 0.0141 1.0096 0.5367 0.202 Uiso 1 1 calc R
H8B H 0.0341 0.9689 0.5621 0.202 Uiso 1 1 calc R
H8C H 0.0228 0.9176 0.5061 0.202 Uiso 1 1 calc R
C9 C 0.03676(9) 1.2329(6) 0.5331(4) 0.143(3) Uani 1 1 d .
H9A H 0.0454 1.2809 0.5222 0.214 Uiso 1 1 calc R
H9B H 0.0412 1.214 0.5714 0.214 Uiso 1 1 calc R
H9C H 0.0254 1.2722 0.5273 0.214 Uiso 1 1 calc R
C10 C 0.01634(9) 1.1288(6) 0.4265(3) 0.153(4) Uani 1 1 d .
H10A H 0.0212 1.1806 0.4045 0.23 Uiso 1 1 calc R
H10B H 0.006 1.1626 0.435 0.23 Uiso 1 1 calc R
H10C H 0.0129 1.0594 0.4064 0.23 Uiso 1 1 calc R
C11 C 0.07003(8) 0.9389(7) 0.5467(3) 0.067(2) Uani 1 1 d .
C12 C 0.06906(8) 1.0018(6) 0.5913(4) 0.078(2) Uani 1 1 d .
H12 H 0.0675 1.0801 0.5868 0.094 Uiso 1 1 calc R
C13 C 0.07021(10) 0.9557(7) 0.6432(3) 0.095(3) Uani 1 1 d .
H13 H 0.0698 1.0016 0.673 0.114 Uiso 1 1 calc R
C14 C 0.07190(9) 0.8450(7) 0.6482(3) 0.077(2) Uani 1 1 d .
C15 C 0.07418(9) 0.7792(6) 0.6051(4) 0.094(3) Uani 1 1 d .
H15 H 0.0762 0.7014 0.6101 0.113 Uiso 1 1 calc R
C16 C 0.07348(9) 0.8271(7) 0.5559(3) 0.087(3) Uani 1 1 d .
H16 H 0.0754 0.7819 0.5275 0.104 Uiso 1 1 calc R
C17 C 0.07268(14) 0.7912(6) 0.7028(3) 0.075(2) Uani 1 1 d .
C18 C 0.08787(13) 0.7741(6) 0.7420(4) 0.074(2) Uani 1 1 d .
C19 C 0.10435(17) 0.7987(7) 0.7309(3) 0.111(3) Uani 1 1 d .
H19 H 0.104 0.8317 0.6969 0.133 Uiso 1 1 calc R
C20 C 0.12082(15) 0.7787(9) 0.7651(5) 0.151(4) Uani 1 1 d .
H20 H 0.1314 0.7979 0.7557 0.181 Uiso 1 1 calc R
C21 C 0.12096(14) 0.7278(9) 0.8150(6) 0.159(5) Uani 1 1 d .
H21 H 0.132 0.711 0.8396 0.19 Uiso 1 1 calc R
C22 C 0.10503(16) 0.7011(6) 0.8292(3) 0.103(3) Uani 1 1 d .
H22 H 0.1057 0.6675 0.8632 0.124 Uiso 1 1 calc R
C23 C 0.08781(14) 0.7243(6) 0.7929(3) 0.082(3) Uani 1 1 d .
C24 C 0.07199(15) 0.7050(6) 0.8045(4) 0.090(3) Uani 1 1 d .
C25 C 0.05598(18) 0.7269(9) 0.7666(5) 0.156(5) Uani 1 1 d .
C26 C 0.0391(2) 0.7018(12) 0.7772(5) 0.251(8) Uani 1 1 d .
H26 H 0.039 0.6888 0.8137 0.301 Uiso 1 1 calc R
C27 C 0.0229(2) 0.6950(19) 0.7379(7) 0.393(15) Uani 1 1 d .
H27 H 0.0128 0.6546 0.742 0.472 Uiso 1 1 calc R
C28 C 0.02350(17) 0.7567(16) 0.6912(10) 0.398(14) Uani 1 1 d .
H28 H 0.0125 0.7832 0.6695 0.477 Uiso 1 1 calc R
C29 C 0.03906(18) 0.7834(11) 0.6732(5) 0.240(7) Uani 1 1 d .
H29 H 0.0382 0.8102 0.6378 0.288 Uiso 1 1 calc R
C30 C 0.05625(15) 0.7675(8) 0.7121(4) 0.134(4) Uani 1 1 d .
C31 C 0.07139(10) 0.6525(8) 0.8560(4) 0.084(3) Uani 1 1 d .
C32 C 0.07395(10) 0.7191(7) 0.9019(4) 0.104(3) Uani 1 1 d .
H32 H 0.0764 0.796 0.8989 0.125 Uiso 1 1 calc R
C33 C 0.07306(9) 0.6772(6) 0.9528(4) 0.099(3) Uani 1 1 d .
H33 H 0.075 0.7248 0.9834 0.119 Uiso 1 1 calc R
C34 C 0.06935(9) 0.5660(7) 0.9568(3) 0.072(2) Uani 1 1 d .
C35 C 0.06761(9) 0.4966(6) 0.9116(4) 0.091(3) Uani 1 1 d .
H35 H 0.0657 0.419 0.9148 0.109 Uiso 1 1 calc R
C36 C 0.06859(10) 0.5399(7) 0.8624(3) 0.100(3) Uani 1 1 d .
H36 H 0.0673 0.4913 0.8324 0.12 Uiso 1 1 calc R
C37 C 0.06749(11) 0.5136(6) 1.0096(3) 0.073(2) Uani 1 1 d .
C38 C 0.05343(10) 0.4450(6) 1.0109(3) 0.086(2) Uani 1 1 d .
H38 H 0.0545 0.4119 1.0453 0.103 Uiso 1 1 calc R
C39 C 0.03534(10) 0.2713(5) 0.9226(4) 0.159(4) Uani 1 1 d .
H39A H 0.0405 0.2126 0.9485 0.239 Uiso 1 1 calc R
H39B H 0.0431 0.2857 0.8989 0.239 Uiso 1 1 calc R
H39C H 0.0237 0.2472 0.9009 0.239 Uiso 1 1 calc R
C40 C 0.02313(10) 0.5183(6) 0.9131(3) 0.137(3) Uani 1 1 d .
H40A H 0.0194 0.5792 0.9332 0.206 Uiso 1 1 calc R
H40B H 0.0128 0.4903 0.8857 0.206 Uiso 1 1 calc R
H40C H 0.032 0.5458 0.8953 0.206 Uiso 1 1 calc R
C41 C 0.01675(9) 0.3688(6) 1.0021(3) 0.140(3) Uani 1 1 d .
H41A H 0.0212 0.3047 1.0254 0.211 Uiso 1 1 calc R
H41B H 0.0052 0.3508 0.9781 0.211 Uiso 1 1 calc R
H41C H 0.0156 0.4332 1.0245 0.211 Uiso 1 1 calc R
C42 C 0.08130(12) 0.5462(6) 1.0601(3) 0.076(2) Uani 1 1 d .
C43 C 0.07623(11) 0.5720(6) 1.1046(3) 0.104(3) Uani 1 1 d .
H43 H 0.0637 0.5727 1.0987 0.124 Uiso 1 1 calc R
C44 C 0.07118(14) 0.5539(8) 1.2158(4) 0.225(5) Uani 1 1 d .
H44A H 0.077 0.5522 1.2545 0.337 Uiso 1 1 calc R
H44B H 0.0672 0.4786 1.2035 0.337 Uiso 1 1 calc R
H44C H 0.061 0.6042 1.2091 0.337 Uiso 1 1 calc R
C45 C 0.10983(16) 0.5411(8) 1.2049(4) 0.281(8) Uani 1 1 d .
H45A H 0.1081 0.4672 1.219 0.421 Uiso 1 1 calc R
H45B H 0.1168 0.5876 1.2343 0.421 Uiso 1 1 calc R
H45C H 0.1162 0.5335 1.1768 0.421 Uiso 1 1 calc R
C46 C 0.08940(13) 0.7616(6) 1.1846(3) 0.184(4) Uani 1 1 d .
H46A H 0.094 0.7797 1.2229 0.277 Uiso 1 1 calc R
H46B H 0.0776 0.794 1.1712 0.277 Uiso 1 1 calc R
H46C H 0.0973 0.7922 1.1642 0.277 Uiso 1 1 calc R
C47 C 0.09975(12) 0.5441(8) 1.0539(3) 0.077(2) Uani 1 1 d .
C48 C 0.11122(14) 0.6306(7) 1.0751(4) 0.116(3) Uani 1 1 d .
H48 H 0.1075 0.6867 1.096 0.14 Uiso 1 1 calc R
C49 C 0.12767(16) 0.6367(7) 1.0665(4) 0.121(3) Uani 1 1 d .
H49 H 0.1356 0.6932 1.0842 0.145 Uiso 1 1 calc R
C50 C 0.13335(12) 0.5606(9) 1.0318(4) 0.097(3) Uani 1 1 d .
C51 C 0.12278(12) 0.4695(7) 1.0137(3) 0.087(3) Uani 1 1 d .
H51 H 0.1269 0.4118 0.9946 0.104 Uiso 1 1 calc R
C52 C 0.10637(12) 0.4621(6) 1.0234(3) 0.074(2) Uani 1 1 d .
H52 H 0.0991 0.4001 1.0094 0.088 Uiso 1 1 calc R
C53 C 0.15032(14) 0.5731(8) 1.0121(3) 0.094(3) Uani 1 1 d .
C54 C 0.15198(15) 0.6724(7) 0.9855(4) 0.089(3) Uani 1 1 d .
C55 C 0.13718(12) 0.7562(11) 0.9684(4) 0.131(3) Uani 1 1 d .
H55 H 0.1262 0.7472 0.9775 0.157 Uiso 1 1 calc R
C56 C 0.1406(2) 0.8533(9) 0.9368(4) 0.181(7) Uani 1 1 d .
H56 H 0.1316 0.9085 0.9289 0.217 Uiso 1 1 calc R
C57 C 0.15580(18) 0.8745(14) 0.9165(7) 0.259(9) Uani 1 1 d .
H57 H 0.1575 0.9383 0.8964 0.31 Uiso 1 1 calc R
C58 C 0.16744(13) 0.7873(10) 0.9309(4) 0.138(4) Uani 1 1 d .
H58 H 0.1773 0.7917 0.9159 0.165 Uiso 1 1 calc R
C59 C 0.16756(17) 0.6841(8) 0.9665(4) 0.090(3) Uani 1 1 d .
C60 C 0.18000(13) 0.6040(10) 0.9729(4) 0.100(3) Uani 1 1 d .
C61 C 0.17917(15) 0.5157(9) 1.0047(4) 0.093(3) Uani 1 1 d .
C62 C 0.19358(12) 0.4362(10) 1.0196(4) 0.117(3) Uani 1 1 d .
H62 H 0.2039 0.4487 1.0071 0.14 Uiso 1 1 calc R
C63 C 0.19310(14) 0.3464(10) 1.0498(5) 0.145(4) Uani 1 1 d .
H63 H 0.2024 0.2931 1.0568 0.174 Uiso 1 1 calc R
C64 C 0.17787(17) 0.3334(8) 1.0713(4) 0.133(4) Uani 1 1 d .
H64 H 0.1774 0.2709 1.0937 0.16 Uiso 1 1 calc R
C65 C 0.16410(11) 0.4073(8) 1.0609(3) 0.103(3) Uani 1 1 d .
H65 H 0.1545 0.3981 1.077 0.123 Uiso 1 1 calc R
C66 C 0.16436(15) 0.4979(8) 1.0256(4) 0.092(3) Uani 1 1 d .
C67 C 0.19540(14) 0.6201(8) 0.9511(5) 0.098(3) Uani 1 1 d .
C68 C 0.20848(16) 0.6930(9) 0.9748(4) 0.122(4) Uani 1 1 d .
H68 H 0.2073 0.7337 1.0055 0.147 Uiso 1 1 calc R
C69 C 0.22354(12) 0.7108(6) 0.9562(4) 0.093(3) Uani 1 1 d .
H69 H 0.232 0.7647 0.9733 0.112 Uiso 1 1 calc R
C70 C 0.22625(14) 0.6493(8) 0.9119(4) 0.084(3) Uani 1 1 d .
C71 C 0.21331(18) 0.5772(9) 0.8897(4) 0.158(5) Uani 1 1 d .
H71 H 0.2146 0.5343 0.8597 0.19 Uiso 1 1 calc R
C72 C 0.19794(17) 0.5613(10) 0.9079(5) 0.171(5) Uani 1 1 d .
H72 H 0.1892 0.5092 0.89 0.206 Uiso 1 1 calc R
C73 C 0.24292(13) 0.6620(7) 0.8947(3) 0.089(3) Uani 1 1 d .
C74 C 0.25633(12) 0.5869(6) 0.9049(3) 0.135(4) Uani 1 1 d .
H74 H 0.2654 0.5993 0.8872 0.162 Uiso 1 1 calc R
C75 C 0.25175(16) 0.4638(8) 1.0094(4) 0.245(6) Uani 1 1 d .
H75A H 0.2403 0.4261 1.0031 0.368 Uiso 1 1 calc R
H75B H 0.2505 0.5413 1.0199 0.368 Uiso 1 1 calc R
H75C H 0.2604 0.4255 1.0384 0.368 Uiso 1 1 calc R
C76 C 0.2597(3) 0.3475(8) 0.9140(5) 0.384(12) Uani 1 1 d .
H76A H 0.27 0.3508 0.899 0.575 Uiso 1 1 calc R
H76B H 0.2488 0.3428 0.8845 0.575 Uiso 1 1 calc R
H76C H 0.2605 0.2815 0.9371 0.575 Uiso 1 1 calc R
C77 C 0.28795(18) 0.4718(12) 0.9869(8) 0.434(14) Uani 1 1 d .
H77A H 0.2901 0.4906 1.0253 0.65 Uiso 1 1 calc R
H77B H 0.2931 0.5297 0.9685 0.65 Uiso 1 1 calc R
H77C H 0.2935 0.3999 0.9832 0.65 Uiso 1 1 calc R
C78 C 0.24441(12) 0.7648(6) 0.8607(3) 0.081(2) Uani 1 1 d .
C79 C 0.25945(11) 0.8280(6) 0.8666(3) 0.115(3) Uani 1 1 d .
H79 H 0.2688 0.8115 0.8975 0.138 Uiso 1 1 calc R
C80 C 0.25703(12) 1.0731(6) 0.8451(4) 0.191(4) Uani 1 1 d .
H80A H 0.2444 1.0697 0.8442 0.287 Uiso 1 1 calc R
H80B H 0.259 1.1326 0.8211 0.287 Uiso 1 1 calc R
H80C H 0.264 1.0886 0.8821 0.287 Uiso 1 1 calc R
C81 C 0.25458(14) 0.9189(8) 0.7488(3) 0.231(6) Uani 1 1 d .
H81A H 0.2419 0.9375 0.7391 0.346 Uiso 1 1 calc R
H81B H 0.2561 0.8408 0.7397 0.346 Uiso 1 1 calc R
H81C H 0.2608 0.9672 0.7288 0.346 Uiso 1 1 calc R
C82 C 0.28883(11) 0.9446(8) 0.8345(5) 0.221(5) Uani 1 1 d .
H82A H 0.2926 1.021 0.8295 0.332 Uiso 1 1 calc R
H82B H 0.2923 0.8951 0.8086 0.332 Uiso 1 1 calc R
H82C H 0.2945 0.9199 0.8713 0.332 Uiso 1 1 calc R
C83 C 0.22732(11) 0.7912(8) 0.8161(4) 0.085(3) Uani 1 1 d .
C84 C 0.21695(13) 0.8838(8) 0.8210(3) 0.118(3) Uani 1 1 d .
H84 H 0.2205 0.9288 0.8525 0.142 Uiso 1 1 calc R
C85 C 0.20193(11) 0.9126(7) 0.7825(4) 0.117(3) Uani 1 1 d .
H85 H 0.1951 0.9757 0.787 0.14 Uiso 1 1 calc R
C86 C 0.19696(13) 0.8443(8) 0.7355(4) 0.095(3) Uani 1 1 d .
C87 C 0.20743(13) 0.7558(7) 0.7330(3) 0.117(3) Uani 1 1 d .
H87 H 0.2039 0.7104 0.7017 0.141 Uiso 1 1 calc R
C88 C 0.22241(13) 0.7244(7) 0.7703(4) 0.138(4) Uani 1 1 d .
H88 H 0.2291 0.661 0.7653 0.166 Uiso 1 1 calc R
C89 C 0.18029(14) 0.8727(8) 0.6929(4) 0.093(3) Uani 1 1 d .
C90 C 0.16629(14) 0.8009(8) 0.6833(4) 0.082(3) Uani 1 1 d .
C91 C 0.16552(17) 0.7043(11) 0.7165(5) 0.170(4) Uani 1 1 d .
H91 H 0.1752 0.689 0.7466 0.204 Uiso 1 1 calc R
C92 C 0.1509(2) 0.6331(12) 0.7054(6) 0.209(6) Uani 1 1 d .
H92 H 0.1512 0.5646 0.7242 0.251 Uiso 1 1 calc R
C93 C 0.13564(15) 0.6667(12) 0.6650(6) 0.180(5) Uani 1 1 d .
H93 H 0.125 0.6251 0.66 0.216 Uiso 1 1 calc R
C94 C 0.13602(15) 0.7597(9) 0.6326(4) 0.135(4) Uani 1 1 d .
H94 H 0.1259 0.7777 0.6044 0.162 Uiso 1 1 calc R
C95 C 0.15119(14) 0.8270(8) 0.6409(4) 0.087(3) Uani 1 1 d .
C96 C 0.15072(13) 0.9230(8) 0.6102(4) 0.098(3) Uani 1 1 d .
C97 C 0.16546(13) 0.9897(7) 0.6153(4) 0.082(3) Uani 1 1 d .
C98 C 0.16595(12) 1.0755(8) 0.5810(4) 0.109(3) Uani 1 1 d .
H98 H 0.1562 1.088 0.5507 0.131 Uiso 1 1 calc R
C99 C 0.18000(17) 1.1420(8) 0.5896(4) 0.142(4) Uani 1 1 d .
H99 H 0.1797 1.2048 0.5668 0.171 Uiso 1 1 calc R
C100 C 0.19590(13) 1.1215(9) 0.6330(5) 0.154(4) Uani 1 1 d .
H100 H 0.2056 1.1715 0.6392 0.185 Uiso 1 1 calc R
C101 C 0.19645(12) 1.0302(8) 0.6639(4) 0.129(4) Uani 1 1 d .
H101 H 0.2072 1.0105 0.6893 0.155 Uiso 1 1 calc R
C102 C 0.18117(13) 0.9635(8) 0.6587(4) 0.083(2) Uani 1 1 d .
C103 C 0.13380(12) 0.9405(7) 0.5658(4) 0.085(2) Uani 1 1 d .
C104 C 0.12297(11) 1.0300(6) 0.5672(3) 0.080(2) Uani 1 1 d .
H104 H 0.127 1.0873 0.5931 0.096 Uiso 1 1 calc R
C105 C 0.10610(11) 1.0390(6) 0.5315(3) 0.076(2) Uani 1 1 d .
H105 H 0.099 1.1021 0.5337 0.092 Uiso 1 1 calc R
C106 C 0.09961(11) 0.9578(7) 0.4929(3) 0.071(2) Uani 1 1 d .
C107 C 0.11201(13) 0.8715(6) 0.4906(3) 0.107(3) Uani 1 1 d .
H107 H 0.1086 0.8166 0.4632 0.129 Uiso 1 1 calc R
C108 C 0.12827(12) 0.8627(7) 0.5247(4) 0.133(4) Uani 1 1 d .
H108 H 0.1359 0.8037 0.5206 0.16 Uiso 1 1 calc R
Si1 Si 0.08598(4) 0.8934(2) 0.35308(11) 0.1215(10) Uani 1 1 d .
Si2 Si 0.03345(3) 1.0981(2) 0.49063(10) 0.1057(9) Uani 1 1 d .
Si3 Si 0.03282(3) 0.4031(2) 0.96047(10) 0.1100(9) Uani 1 1 d .
Si4 Si 0.08805(4) 0.6071(2) 1.17598(11) 0.1415(11) Uani 1 1 d .
Si5 Si 0.25900(6) 0.4609(3) 0.95010(18) 0.2004(17) Uani 1 1 d .
Si6 Si 0.26395(4) 0.9404(2) 0.82293(12) 0.1283(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.244(11) 0.142(8) 0.215(12) -0.021(8) 0.144(9) -0.080(8)
C2 0.357(14) 0.096(7) 0.156(10) -0.053(6) 0.138(9) -0.061(8)
C3 0.291(12) 0.258(11) 0.044(6) 0.001(7) 0.033(7) 0.046(10)
C4 0.098(6) 0.119(6) 0.057(6) -0.011(5) 0.021(5) -0.006(5)
C5 0.079(6) 0.068(5) 0.041(6) 0.014(4) 0.015(5) -0.005(4)
C6 0.095(7) 0.064(5) 0.042(6) -0.007(4) 0.018(5) -0.013(5)
C7 0.079(6) 0.072(5) 0.068(6) 0.015(4) 0.017(5) -0.010(4)
C8 0.084(6) 0.163(8) 0.164(9) 0.051(7) 0.044(6) -0.021(5)
C9 0.144(8) 0.113(7) 0.186(10) 0.009(7) 0.070(7) 0.025(6)
C10 0.103(6) 0.205(9) 0.118(8) 0.056(7) -0.033(6) -0.004(6)
C11 0.100(6) 0.092(6) 0.013(5) 0.009(5) 0.022(4) -0.001(5)
C12 0.104(6) 0.078(6) 0.054(6) -0.012(5) 0.023(5) 0.011(4)
C13 0.168(8) 0.074(6) 0.049(7) -0.006(5) 0.037(5) -0.025(6)
C14 0.132(7) 0.064(6) 0.047(6) 0.008(5) 0.042(5) -0.017(5)
C15 0.141(7) 0.061(6) 0.078(7) 0.012(6) 0.025(6) 0.005(5)
C16 0.156(7) 0.075(6) 0.039(6) 0.020(5) 0.044(5) 0.022(5)
C17 0.083(7) 0.096(6) 0.048(6) 0.013(5) 0.021(6) 0.001(5)
C18 0.063(7) 0.088(6) 0.074(8) 0.000(5) 0.026(6) 0.004(5)
C19 0.131(9) 0.165(8) 0.027(6) 0.006(5) 0.003(7) 0.016(7)
C20 0.161(12) 0.245(12) 0.051(7) 0.014(8) 0.036(8) -0.011(9)
C21 0.102(9) 0.222(12) 0.157(14) -0.020(10) 0.044(9) -0.032(8)
C22 0.146(9) 0.131(7) 0.020(5) 0.011(5) -0.001(7) 0.033(7)
C23 0.136(9) 0.094(6) 0.028(6) 0.029(5) 0.040(6) -0.026(6)
C24 0.129(9) 0.106(6) 0.053(7) 0.049(5) 0.060(7) 0.006(6)
C25 0.137(11) 0.234(11) 0.102(10) 0.119(8) 0.041(9) 0.062(9)
C26 0.107(10) 0.48(2) 0.185(14) 0.227(14) 0.071(10) 0.069(12)
C27 0.151(15) 0.82(4) 0.224(17) 0.36(2) 0.081(12) 0.100(19)
C28 0.086(11) 0.67(3) 0.44(3) 0.35(3) 0.060(15) 0.040(14)
C29 0.108(9) 0.423(18) 0.174(12) 0.218(12) 0.007(9) 0.014(11)
C30 0.094(9) 0.190(9) 0.115(10) 0.092(7) 0.023(8) 0.010(7)
C31 0.121(7) 0.091(7) 0.050(7) -0.001(6) 0.039(5) 0.047(6)
C32 0.172(8) 0.069(6) 0.094(8) 0.033(7) 0.077(7) 0.007(5)
C33 0.144(7) 0.047(6) 0.113(9) 0.002(5) 0.044(6) 0.011(5)
C34 0.112(6) 0.088(6) 0.022(5) 0.001(5) 0.025(4) 0.017(5)
C35 0.156(8) 0.070(6) 0.058(6) 0.024(5) 0.047(6) -0.012(5)
C36 0.187(8) 0.056(6) 0.057(7) 0.015(5) 0.035(6) 0.033(5)
C37 0.106(7) 0.062(5) 0.060(6) 0.017(5) 0.038(6) 0.016(5)
C38 0.103(7) 0.093(6) 0.069(6) 0.018(5) 0.035(5) -0.008(5)
C39 0.187(9) 0.081(6) 0.187(10) -0.032(6) 0.008(7) -0.019(6)
C40 0.151(8) 0.131(7) 0.122(8) 0.020(6) 0.020(6) 0.032(6)
C41 0.098(6) 0.174(8) 0.163(9) 0.013(7) 0.057(6) -0.015(6)
C42 0.094(7) 0.079(5) 0.049(6) -0.003(5) 0.005(6) 0.004(5)
C43 0.175(8) 0.107(6) 0.042(6) -0.012(5) 0.052(6) 0.027(5)
C44 0.397(16) 0.226(11) 0.108(9) -0.023(8) 0.167(10) -0.122(11)
C45 0.382(17) 0.185(10) 0.206(13) 0.011(9) -0.051(12) 0.162(11)
C46 0.350(13) 0.099(7) 0.092(8) -0.018(6) 0.036(8) 0.040(7)
C47 0.073(7) 0.087(6) 0.074(7) 0.000(5) 0.027(5) -0.017(6)
C48 0.090(7) 0.115(8) 0.159(10) -0.040(6) 0.059(7) -0.018(7)
C49 0.140(10) 0.106(7) 0.131(9) -0.041(6) 0.060(8) 0.002(7)
C50 0.081(7) 0.105(8) 0.114(8) 0.003(6) 0.041(6) -0.035(7)
C51 0.066(6) 0.102(7) 0.102(7) 0.001(5) 0.039(6) -0.004(6)
C52 0.096(7) 0.067(5) 0.063(6) -0.019(4) 0.030(5) -0.005(5)
C53 0.115(9) 0.067(7) 0.096(7) 0.011(5) 0.022(6) -0.022(6)
C54 0.103(8) 0.063(7) 0.112(8) -0.012(6) 0.047(7) -0.011(6)
C55 0.128(9) 0.173(10) 0.094(8) -0.027(8) 0.033(7) 0.017(9)
C56 0.32(2) 0.096(8) 0.084(9) 0.030(7) -0.022(10) 0.024(10)
C57 0.190(14) 0.279(19) 0.35(2) 0.117(16) 0.146(14) 0.089(13)
C58 0.113(9) 0.149(10) 0.147(10) -0.040(9) 0.026(7) -0.011(8)
C59 0.138(10) 0.048(6) 0.100(8) 0.004(5) 0.058(7) -0.027(6)
C60 0.085(7) 0.100(8) 0.138(9) 0.047(7) 0.070(6) -0.008(7)
C61 0.107(9) 0.096(8) 0.093(8) 0.009(6) 0.060(7) -0.019(7)
C62 0.115(8) 0.146(9) 0.106(8) 0.052(7) 0.058(6) 0.011(8)
C63 0.119(9) 0.181(11) 0.155(11) 0.057(9) 0.070(8) 0.000(8)
C64 0.143(10) 0.116(8) 0.141(9) 0.073(7) 0.038(8) 0.004(8)
C65 0.091(7) 0.115(8) 0.097(8) 0.023(7) 0.015(6) -0.003(6)
C66 0.116(9) 0.082(7) 0.080(7) 0.032(6) 0.029(7) 0.011(7)
C67 0.105(9) 0.091(7) 0.093(9) 0.004(6) 0.015(7) -0.030(6)
C68 0.118(9) 0.131(9) 0.155(11) 0.003(8) 0.102(9) 0.022(7)
C69 0.093(8) 0.076(6) 0.110(9) -0.007(6) 0.025(6) -0.027(5)
C70 0.095(8) 0.094(7) 0.069(8) 0.000(5) 0.035(7) 0.007(6)
C71 0.167(11) 0.210(12) 0.113(10) -0.064(8) 0.062(9) -0.081(10)
C72 0.189(13) 0.244(13) 0.111(10) -0.092(9) 0.092(9) -0.067(10)
C73 0.109(8) 0.089(7) 0.070(6) 0.024(5) 0.023(6) 0.015(6)
C74 0.173(9) 0.114(7) 0.144(9) 0.050(6) 0.088(7) 0.071(7)
C75 0.437(18) 0.188(10) 0.178(12) 0.102(9) 0.201(13) 0.080(11)
C76 0.89(4) 0.080(8) 0.164(13) 0.034(8) 0.112(18) 0.039(14)
C77 0.303(18) 0.277(17) 0.71(4) 0.28(2) 0.11(2) 0.160(14)
C78 0.119(8) 0.058(6) 0.058(6) 0.002(5) 0.010(6) 0.027(5)
C79 0.125(7) 0.098(7) 0.109(8) 0.014(6) 0.005(6) -0.040(6)
C80 0.295(12) 0.075(6) 0.242(12) 0.030(7) 0.140(10) 0.035(7)
C81 0.371(15) 0.238(11) 0.070(8) 0.009(7) 0.032(9) -0.156(11)
C82 0.143(9) 0.203(11) 0.327(17) 0.038(10) 0.077(9) -0.041(8)
C83 0.082(7) 0.096(7) 0.089(8) 0.044(6) 0.042(6) 0.015(6)
C84 0.107(8) 0.148(8) 0.086(8) -0.035(6) 0.000(6) 0.037(7)
C85 0.089(7) 0.164(9) 0.086(7) -0.015(7) 0.001(6) 0.055(6)
C86 0.115(8) 0.094(7) 0.061(7) -0.014(6) -0.003(6) -0.008(6)
C87 0.156(9) 0.096(7) 0.080(8) -0.009(6) -0.004(7) 0.049(6)
C88 0.175(10) 0.130(8) 0.064(7) -0.016(6) -0.055(7) 0.045(7)
C89 0.096(8) 0.100(7) 0.089(8) 0.038(6) 0.032(7) -0.005(6)
C90 0.076(7) 0.085(7) 0.084(7) 0.026(6) 0.021(6) 0.015(6)
C91 0.166(12) 0.178(11) 0.163(11) 0.067(10) 0.036(9) 0.017(9)
C92 0.181(14) 0.260(16) 0.194(15) 0.045(12) 0.064(12) -0.098(13)
C93 0.112(9) 0.198(13) 0.195(14) 0.003(10) -0.024(9) -0.038(10)
C94 0.146(11) 0.102(8) 0.154(11) 0.051(7) 0.033(8) 0.010(8)
C95 0.076(7) 0.082(7) 0.107(9) 0.003(6) 0.033(7) -0.006(7)
C96 0.089(8) 0.083(7) 0.106(8) 0.027(6) 0.001(6) 0.001(6)
C97 0.087(8) 0.053(6) 0.112(8) 0.010(6) 0.037(7) -0.005(5)
C98 0.085(7) 0.099(8) 0.127(9) 0.036(7) -0.001(6) -0.013(6)
C99 0.125(9) 0.147(10) 0.146(10) 0.066(8) 0.017(8) 0.015(8)
C100 0.107(9) 0.123(9) 0.219(13) 0.059(8) 0.021(9) 0.011(7)
C101 0.076(8) 0.098(7) 0.206(12) 0.046(7) 0.019(7) 0.005(6)
C102 0.064(7) 0.120(8) 0.067(7) 0.011(6) 0.018(6) 0.008(6)
C103 0.095(7) 0.053(6) 0.102(8) -0.006(5) 0.017(6) -0.016(6)
C104 0.074(6) 0.049(5) 0.111(7) -0.015(5) 0.013(6) -0.010(5)
C105 0.084(7) 0.069(6) 0.080(6) -0.005(5) 0.030(5) 0.020(5)
C106 0.090(7) 0.067(5) 0.056(6) 0.002(5) 0.018(5) 0.010(5)
C107 0.111(7) 0.075(6) 0.112(8) -0.040(5) -0.015(6) 0.010(6)
C108 0.101(7) 0.109(7) 0.145(9) -0.058(7) -0.048(7) 0.034(6)
Si1 0.185(3) 0.112(2) 0.084(2) -0.0171(18) 0.065(2) -0.0261(19)
Si2 0.0889(19) 0.126(2) 0.105(2) 0.0276(18) 0.0294(16) 0.0094(16)
Si3 0.106(2) 0.113(2) 0.108(2) 0.0005(18) 0.0208(18) 0.0020(16)
Si4 0.236(3) 0.115(2) 0.068(2) -0.0123(17) 0.030(2) 0.008(2)
Si5 0.303(5) 0.131(3) 0.198(4) 0.080(3) 0.120(4) 0.100(3)
Si6 0.148(3) 0.116(2) 0.132(3) 0.0072(19) 0.056(2) -0.0295(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 C4 Si1 137.9(6)
C4 C5 C106 123.1(8)
C4 C5 C6 123.3(7)
C106 C5 C6 113.6(7)
C7 C6 C11 121.8(8)
C7 C6 C5 119.8(7)
C11 C6 C5 118.3(7)
C6 C7 Si2 132.8(6)
C16 C11 C12 116.0(7)
C16 C11 C6 121.4(7)
C12 C11 C6 122.6(8)
C11 C12 C13 123.7(7)
C14 C13 C12 117.2(8)
C13 C14 C15 120.7(8)
C13 C14 C17 119.1(8)
C15 C14 C17 120.0(8)
C16 C15 C14 120.3(7)
C11 C16 C15 121.6(8)
C18 C17 C30 120.8(9)
C18 C17 C14 124.2(9)
C30 C17 C14 114.9(9)
C17 C18 C19 119.0(10)
C17 C18 C23 121.9(9)
C19 C18 C23 119.0(9)
C20 C19 C18 125.6(10)
C21 C20 C19 116.0(11)
C20 C21 C22 121.7(11)
C21 C22 C23 121.4(9)
C24 C23 C22 124.7(9)
C24 C23 C18 118.9(9)
C22 C23 C18 116.3(8)
C23 C24 C25 121.1(10)
C23 C24 C31 120.5(9)
C25 C24 C31 118.3(9)
C26 C25 C24 121.8(11)
C26 C25 C30 118.7(10)
C24 C25 C30 119.3(11)
C27 C26 C25 125.1(12)
C26 C27 C28 110.8(15)
C29 C28 C27 126.9(13)
C28 C29 C30 117.0(11)
C17 C30 C29 125.6(10)
C17 C30 C25 117.6(10)
C29 C30 C25 116.7(10)
C36 C31 C32 116.9(8)
C36 C31 C24 124.4(8)
C32 C31 C24 118.7(9)
C33 C32 C31 123.0(8)
C34 C33 C32 118.3(8)
C33 C34 C35 119.4(8)
C33 C34 C37 122.2(8)
C35 C34 C37 118.3(8)
C34 C35 C36 120.9(7)
C31 C36 C35 121.4(8)
C38 C37 C34 121.5(8)
C38 C37 C42 122.2(8)
C34 C37 C42 116.2(7)
C37 C38 Si3 134.3(6)
C43 C42 C47 126.9(8)
C43 C42 C37 119.3(8)
C47 C42 C37 113.8(8)
C42 C43 Si4 134.9(7)
C48 C47 C52 116.0(8)
C48 C47 C42 119.5(9)
C52 C47 C42 124.3(8)
C49 C48 C47 121.3(9)
C48 C49 C50 121.8(9)
C51 C50 C49 117.5(9)
C51 C50 C53 117.4(10)
C49 C50 C53 125.1(10)
C52 C51 C50 120.0(9)
C51 C52 C47 122.7(7)
C54 C53 C66 120.5(10)
C54 C53 C50 116.0(10)
C66 C53 C50 123.0(9)
C53 C54 C59 116.4(9)
C53 C54 C55 123.3(11)
C59 C54 C55 119.5(10)
C56 C55 C54 116.6(10)
C55 C56 C57 128.4(14)
C58 C57 C56 108.6(15)
C57 C58 C59 132.5(12)
C60 C59 C54 122.7(9)
C60 C59 C58 122.8(11)
C54 C59 C58 113.9(10)
C59 C60 C61 119.2(10)
C59 C60 C67 119.9(10)
C61 C60 C67 120.4(10)
C60 C61 C66 121.3(11)
C60 C61 C62 121.4(11)
C66 C61 C62 117.3(10)
C63 C62 C61 123.2(10)
C62 C63 C64 117.3(10)
C65 C64 C63 122.7(9)
C64 C65 C66 118.9(9)
C53 C66 C61 118.6(10)
C53 C66 C65 121.0(11)
C61 C66 C65 120.4(10)
C68 C67 C72 116.3(11)
C68 C67 C60 120.7(11)
C72 C67 C60 123.0(11)
C69 C68 C67 123.1(11)
C68 C69 C70 120.6(9)
C71 C70 C69 115.2(9)
C71 C70 C73 124.3(11)
C69 C70 C73 120.5(10)
C70 C71 C72 124.1(11)
C67 C72 C71 120.8(11)
C74 C73 C70 124.6(8)
C74 C73 C78 118.4(9)
C70 C73 C78 116.9(8)
C73 C74 Si5 127.5(7)
C79 C78 C73 124.7(7)
C79 C78 C83 121.3(7)
C73 C78 C83 114.0(7)
C78 C79 Si6 128.9(6)
C84 C83 C88 119.5(8)
C84 C83 C78 120.3(9)
C88 C83 C78 120.1(8)
C83 C84 C85 123.0(8)
C84 C85 C86 117.4(8)
C87 C86 C85 117.1(8)
C87 C86 C89 124.3(9)
C85 C86 C89 118.6(9)
C86 C87 C88 127.3(9)
C87 C88 C83 115.7(9)
C90 C89 C102 122.7(9)
C90 C89 C86 119.4(8)
C102 C89 C86 117.0(9)
C89 C90 C95 118.0(10)
C89 C90 C91 123.5(11)
C95 C90 C91 118.3(10)
C92 C91 C90 121.8(11)
C93 C92 C91 117.7(13)
C94 C93 C92 121.1(12)
C93 C94 C95 121.0(11)
C94 C95 C96 119.5(10)
C94 C95 C90 119.5(10)
C96 C95 C90 120.8(9)
C97 C96 C95 121.8(9)
C97 C96 C103 122.3(9)
C95 C96 C103 115.4(9)
C96 C97 C98 122.6(10)
C96 C97 C102 117.6(9)
C98 C97 C102 119.7(9)
C99 C98 C97 120.4(9)
C98 C99 C100 122.0(10)
C101 C100 C99 118.5(10)
C100 C101 C102 120.4(9)
C89 C102 C101 123.6(10)
C89 C102 C97 118.2(9)
C101 C102 C97 118.2(9)
C104 C103 C108 118.1(8)
C104 C103 C96 120.8(8)
C108 C103 C96 121.0(8)
C103 C104 C105 121.7(7)
C106 C105 C104 121.4(7)
C105 C106 C107 114.2(7)
C105 C106 C5 122.2(8)
C107 C106 C5 123.3(8)
C106 C107 C108 124.5(7)
C103 C108 C107 119.7(8)
C1 Si1 C4 116.0(4)
C1 Si1 C2 110.6(4)
C4 Si1 C2 109.4(4)
C1 Si1 C3 108.5(5)
C4 Si1 C3 102.7(4)
C2 Si1 C3 109.3(4)
C9 Si2 C8 109.2(4)
C9 Si2 C7 112.2(3)
C8 Si2 C7 113.1(3)
C9 Si2 C10 107.0(4)
C8 Si2 C10 109.3(3)
C7 Si2 C10 105.8(4)
C40 Si3 C38 112.8(3)
C40 Si3 C39 111.3(4)
C38 Si3 C39 113.4(3)
C40 Si3 C41 108.1(4)
C38 Si3 C41 104.4(4)
C39 Si3 C41 106.2(4)
C45 Si4 C46 111.1(5)
C45 Si4 C43 117.8(4)
C46 Si4 C43 109.7(3)
C45 Si4 C44 108.8(5)
C46 Si4 C44 106.6(4)
C43 Si4 C44 101.9(4)
C76 Si5 C75 124.4(6)
C76 Si5 C74 109.3(5)
C75 Si5 C74 120.6(4)
C76 Si5 C77 96.4(8)
C75 Si5 C77 98.7(7)
C74 Si5 C77 98.8(5)
C80 Si6 C81 111.6(5)
C80 Si6 C79 109.4(4)
C81 Si6 C79 115.5(4)
C80 Si6 C82 107.7(4)
C81 Si6 C82 106.3(5)
C79 Si6 C82 105.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Si1 1.853(8)
C2 Si1 1.876(7)
C3 Si1 1.952(8)
C4 C5 1.374(8)
C4 Si1 1.826(8)
C5 C106 1.503(8)
C5 C6 1.494(9)
C6 C7 1.378(7)
C6 C11 1.475(8)
C7 Si2 1.869(7)
C8 Si2 1.877(7)
C9 Si2 1.930(7)
C10 Si2 1.870(7)
C11 C16 1.376(8)
C11 C12 1.388(8)
C12 C13 1.423(8)
C13 C14 1.338(8)
C14 C15 1.405(9)
C14 C17 1.528(9)
C15 C16 1.375(9)
C17 C18 1.359(9)
C17 C30 1.393(9)
C18 C19 1.420(10)
C18 C23 1.435(9)
C19 C20 1.380(10)
C20 C21 1.415(12)
C21 C22 1.421(10)
C22 C23 1.453(9)
C23 C24 1.363(9)
C24 C25 1.397(10)
C24 C31 1.475(10)
C25 C26 1.446(12)
C25 C30 1.485(11)
C26 C27 1.404(16)
C27 C28 1.417(16)
C28 C29 1.443(14)
C29 C30 1.464(11)
C31 C36 1.385(9)
C31 C32 1.393(9)
C32 C33 1.417(9)
C33 C34 1.374(8)
C34 C35 1.405(8)
C34 C37 1.531(9)
C35 C36 1.383(8)
C37 C38 1.380(8)
C37 C42 1.508(9)
C38 Si3 1.856(7)
C39 Si3 1.892(7)
C40 Si3 1.867(7)
C41 Si3 1.892(7)
C42 C43 1.337(9)
C42 C47 1.490(9)
C43 Si4 1.872(8)
C44 Si4 1.969(9)
C45 Si4 1.850(9)
C46 Si4 1.866(7)
C47 C48 1.387(9)
C47 C52 1.434(8)
C48 C49 1.361(9)
C49 C50 1.423(10)
C50 C51 1.376(9)
C50 C53 1.542(11)
C51 C52 1.371(8)
C53 C54 1.396(10)
C53 C66 1.393(9)
C54 C59 1.429(10)
C54 C55 1.510(10)
C55 C56 1.482(12)
C56 C57 1.435(16)
C57 C58 1.373(14)
C58 C59 1.537(12)
C59 C60 1.346(10)
C60 C61 1.349(10)
C60 C67 1.464(11)
C61 C66 1.410(10)
C61 C62 1.450(10)
C62 C63 1.333(10)
C63 C64 1.443(11)
C64 C65 1.366(9)
C65 C66 1.418(10)
C67 C68 1.364(10)
C67 C72 1.369(11)
C68 C69 1.396(9)
C69 C70 1.413(10)
C70 C71 1.341(10)
C70 C73 1.486(10)
C71 C72 1.409(11)
C73 C74 1.356(9)
C73 C78 1.532(9)
C74 Si5 1.883(8)
C75 Si5 1.753(10)
C76 Si5 1.654(11)
C77 Si5 2.220(14)
C78 C79 1.374(8)
C78 C83 1.550(9)
C79 Si6 1.843(8)
C80 Si6 1.820(8)
C81 Si6 1.869(8)
C82 Si6 1.890(8)
C83 C84 1.400(9)
C83 C88 1.393(9)
C84 C85 1.370(8)
C85 C86 1.426(9)
C86 C87 1.352(9)
C86 C89 1.508(10)
C87 C88 1.360(9)
C89 C90 1.364(9)
C89 C102 1.410(9)
C90 C95 1.418(9)
C90 C91 1.448(11)
C91 C92 1.393(11)
C92 C93 1.424(13)
C93 C94 1.396(12)
C94 C95 1.405(10)
C95 C96 1.389(10)
C96 C97 1.381(9)
C96 C103 1.520(9)
C97 C98 1.361(9)
C97 C102 1.463(9)
C98 C99 1.329(9)
C99 C100 1.459(10)
C100 C101 1.345(10)
C101 C102 1.415(9)
C103 C104 1.373(8)
C103 C108 1.391(9)
C104 C105 1.402(8)
C105 C106 1.388(8)
C106 C107 1.429(8)
C107 C108 1.348(8)
|
1501993.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501993.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501993
loop_
_publ_author_name
'Ehlers, Peter'
'Neubauer, Antje'
'Lochbrunner, Stefan'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
Multiple sonogashira reactions of polychlorinated molecules. Synthesis
and photophysical properties of the first pentaalkynylpyridines.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1618
_journal_page_last 1621
_journal_paper_doi 10.1021/ol2000183
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C50 H35 N'
_chemical_formula_sum 'C50 H35 N'
_chemical_formula_weight 649.79
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 96.518(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.0408(8)
_cell_length_b 11.9207(10)
_cell_length_c 25.282(2)
_cell_measurement_reflns_used 2793
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 53.074
_cell_measurement_theta_min 4.711
_cell_volume 3605.4(5)
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0741
_diffrn_reflns_av_sigmaI/netI 0.0950
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_number 32372
_diffrn_reflns_theta_full 28.03
_diffrn_reflns_theta_max 28.02
_diffrn_reflns_theta_min 2.36
_exptl_absorpt_coefficient_mu 0.068
_exptl_absorpt_correction_T_max 0.9966
_exptl_absorpt_correction_T_min 0.9410
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour orange
_exptl_crystal_density_diffrn 1.197
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1368
_exptl_crystal_size_max 0.90
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.202
_refine_diff_density_min -0.234
_refine_diff_density_rms 0.044
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.907
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 466
_refine_ls_number_reflns 8695
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.907
_refine_ls_R_factor_all 0.1610
_refine_ls_R_factor_gt 0.0594
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1097
_refine_ls_wR_factor_ref 0.1344
_reflns_number_gt 4033
_reflns_number_total 8695
_reflns_threshold_expression >2\s(I)
_cod_data_source_file ol2000183_si_002.cif
_cod_data_source_block is_pe314
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1501993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.75518(12) 0.14587(13) 0.62968(6) 0.0266(4) Uani 1 1 d . . .
C1 C 0.85138(14) 0.12992(16) 0.60845(8) 0.0241(4) Uani 1 1 d . . .
C2 C 0.86832(14) 0.16559(15) 0.55671(7) 0.0229(4) Uani 1 1 d . . .
C3 C 0.78045(15) 0.22060(16) 0.52589(7) 0.0253(4) Uani 1 1 d . . .
C4 C 0.67862(15) 0.23595(16) 0.54743(8) 0.0260(5) Uani 1 1 d . . .
C5 C 0.67062(15) 0.19659(16) 0.59934(8) 0.0265(5) Uani 1 1 d . . .
C6 C 0.93965(15) 0.07340(17) 0.64075(8) 0.0274(5) Uani 1 1 d . . .
C7 C 1.01433(16) 0.02240(17) 0.66498(8) 0.0286(5) Uani 1 1 d . . .
C8 C 1.10744(15) -0.03715(16) 0.69238(8) 0.0282(5) Uani 1 1 d . . .
C9 C 1.20378(16) -0.05221(17) 0.66749(9) 0.0352(5) Uani 1 1 d . . .
H9 H 1.2060 -0.0242 0.6325 0.042 Uiso 1 1 calc R . .
C10 C 1.29657(17) -0.10726(18) 0.69272(10) 0.0409(6) Uani 1 1 d . . .
C11 C 1.2901(2) -0.14950(19) 0.74285(10) 0.0503(7) Uani 1 1 d . . .
H11 H 1.3527 -0.1880 0.7606 0.060 Uiso 1 1 calc R . .
C12 C 1.1950(2) -0.13735(18) 0.76804(9) 0.0485(6) Uani 1 1 d . . .
H12 H 1.1924 -0.1681 0.8025 0.058 Uiso 1 1 calc R . .
C13 C 1.10323(18) -0.08056(17) 0.74324(8) 0.0373(5) Uani 1 1 d . . .
H13 H 1.0380 -0.0713 0.7607 0.045 Uiso 1 1 calc R . .
C14 C 1.40060(17) -0.1207(2) 0.66470(11) 0.0650(8) Uani 1 1 d . . .
H14A H 1.4552 -0.1670 0.6866 0.097 Uiso 1 1 calc R . .
H14B H 1.4330 -0.0468 0.6592 0.097 Uiso 1 1 calc R . .
H14C H 1.3808 -0.1572 0.6302 0.097 Uiso 1 1 calc R . .
C15 C 0.97241(16) 0.14664(16) 0.53642(8) 0.0272(5) Uani 1 1 d . . .
C16 C 1.05979(16) 0.13261(16) 0.51921(8) 0.0291(5) Uani 1 1 d . . .
C17 C 1.16372(15) 0.11840(16) 0.49690(8) 0.0276(5) Uani 1 1 d . . .
C18 C 1.16677(16) 0.13487(16) 0.44256(8) 0.0306(5) Uani 1 1 d . . .
H18 H 1.0997 0.1530 0.4208 0.037 Uiso 1 1 calc R . .
C19 C 1.26542(17) 0.12538(17) 0.41958(8) 0.0331(5) Uani 1 1 d . . .
C20 C 1.36129(17) 0.09633(18) 0.45166(10) 0.0407(6) Uani 1 1 d . . .
H20 H 1.4293 0.0877 0.4364 0.049 Uiso 1 1 calc R . .
C21 C 1.36030(17) 0.07962(19) 0.50552(10) 0.0442(6) Uani 1 1 d . . .
H21 H 1.4275 0.0602 0.5270 0.053 Uiso 1 1 calc R . .
C22 C 1.26195(16) 0.09101(18) 0.52859(9) 0.0379(5) Uani 1 1 d . . .
H22 H 1.2616 0.0802 0.5658 0.045 Uiso 1 1 calc R . .
C23 C 1.2682(2) 0.1463(2) 0.36109(9) 0.0552(7) Uani 1 1 d . . .
H23A H 1.1950 0.1735 0.3454 0.083 Uiso 0.58(2) 1 calc PR A 1
H23B H 1.2862 0.0763 0.3436 0.083 Uiso 0.58(2) 1 calc PR A 1
H23C H 1.3253 0.2028 0.3562 0.083 Uiso 0.58(2) 1 calc PR A 1
H23D H 1.3427 0.1282 0.3514 0.083 Uiso 0.42(2) 1 d PR A 2
H23E H 1.2515 0.2254 0.3531 0.083 Uiso 0.42(2) 1 d PR A 2
H23F H 1.2123 0.0990 0.3406 0.083 Uiso 0.42(2) 1 d PR A 2
C24 C 0.79436(16) 0.26070(17) 0.47399(8) 0.0310(5) Uani 1 1 d . . .
C25 C 0.80765(16) 0.29690(18) 0.43089(9) 0.0354(5) Uani 1 1 d . . .
C26 C 0.82017(17) 0.34067(17) 0.37857(8) 0.0321(5) Uani 1 1 d . . .
C27 C 0.73147(16) 0.39488(17) 0.34937(8) 0.0328(5) Uani 1 1 d . . .
H27 H 0.6641 0.4057 0.3650 0.039 Uiso 1 1 calc R . .
C28 C 0.73785(17) 0.43378(17) 0.29822(8) 0.0326(5) Uani 1 1 d . . .
C29 C 0.83752(19) 0.41829(18) 0.27677(9) 0.0405(6) Uani 1 1 d . . .
H29 H 0.8443 0.4446 0.2418 0.049 Uiso 1 1 calc R . .
C30 C 0.92723(19) 0.36531(18) 0.30526(9) 0.0442(6) Uani 1 1 d . . .
H30 H 0.9949 0.3559 0.2898 0.053 Uiso 1 1 calc R . .
C31 C 0.91936(18) 0.32588(18) 0.35618(9) 0.0397(6) Uani 1 1 d . . .
H31 H 0.9811 0.2891 0.3756 0.048 Uiso 1 1 calc R . .
C32 C 0.64039(18) 0.4900(2) 0.26669(9) 0.0487(6) Uani 1 1 d . . .
H32A H 0.5747 0.4851 0.2862 0.073 Uiso 1 1 calc R . .
H32B H 0.6244 0.4526 0.2321 0.073 Uiso 1 1 calc R . .
H32C H 0.6584 0.5690 0.2611 0.073 Uiso 1 1 calc R . .
C33 C 0.58701(16) 0.29021(17) 0.51731(8) 0.0314(5) Uani 1 1 d . . .
C34 C 0.51089(17) 0.33551(18) 0.49107(9) 0.0360(5) Uani 1 1 d . . .
C35 C 0.41883(16) 0.38895(17) 0.45981(8) 0.0334(5) Uani 1 1 d . . .
C36 C 0.31541(16) 0.39623(17) 0.47885(8) 0.0347(5) Uani 1 1 d . . .
H36 H 0.3068 0.3664 0.5130 0.042 Uiso 1 1 calc R . .
C37 C 0.22414(16) 0.44601(17) 0.44927(9) 0.0351(5) Uani 1 1 d . . .
C38 C 0.23928(18) 0.48900(19) 0.39993(9) 0.0444(6) Uani 1 1 d . . .
H38 H 0.1780 0.5232 0.3790 0.053 Uiso 1 1 calc R . .
C39 C 0.3414(2) 0.4834(2) 0.38039(10) 0.0580(7) Uani 1 1 d . . .
H39 H 0.3499 0.5139 0.3464 0.070 Uiso 1 1 calc R . .
C40 C 0.43156(18) 0.4338(2) 0.41001(10) 0.0525(7) Uani 1 1 d . . .
H40 H 0.5019 0.4303 0.3965 0.063 Uiso 1 1 calc R . .
C41 C 0.11330(17) 0.4538(2) 0.47115(10) 0.0523(7) Uani 1 1 d . . .
H41A H 0.0577 0.4866 0.4442 0.078 Uiso 1 1 calc R . .
H41B H 0.1209 0.5013 0.5030 0.078 Uiso 1 1 calc R . .
H41C H 0.0890 0.3786 0.4805 0.078 Uiso 1 1 calc R . .
C42 C 0.56837(16) 0.20930(17) 0.62335(8) 0.0310(5) Uani 1 1 d . . .
C43 C 0.48347(16) 0.21829(17) 0.64336(8) 0.0333(5) Uani 1 1 d . . .
C44 C 0.38096(15) 0.22846(17) 0.66728(8) 0.0301(5) Uani 1 1 d . . .
C45 C 0.28827(15) 0.28114(17) 0.63998(8) 0.0320(5) Uani 1 1 d . . .
H45 H 0.2940 0.3113 0.6056 0.038 Uiso 1 1 calc R . .
C46 C 0.18801(15) 0.29069(17) 0.66162(8) 0.0304(5) Uani 1 1 d . . .
C47 C 0.18217(16) 0.24668(17) 0.71203(9) 0.0347(5) Uani 1 1 d . . .
H47 H 0.1145 0.2528 0.7278 0.042 Uiso 1 1 calc R . .
C48 C 0.27307(17) 0.19416(18) 0.73955(9) 0.0385(5) Uani 1 1 d . . .
H48 H 0.2671 0.1642 0.7739 0.046 Uiso 1 1 calc R . .
C49 C 0.37262(16) 0.18453(17) 0.71777(8) 0.0342(5) Uani 1 1 d . . .
H49 H 0.4349 0.1483 0.7370 0.041 Uiso 1 1 calc R . .
C50 C 0.08917(15) 0.34867(18) 0.63165(9) 0.0410(6) Uani 1 1 d . . .
H50A H 0.0963 0.4299 0.6369 0.062 Uiso 1 1 calc R . .
H50B H 0.0203 0.3224 0.6449 0.062 Uiso 1 1 calc R . .
H50C H 0.0866 0.3315 0.5936 0.062 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0220(9) 0.0320(10) 0.0261(10) -0.0040(8) 0.0047(7) 0.0020(7)
C1 0.0224(10) 0.0259(11) 0.0240(11) -0.0032(9) 0.0022(9) 0.0007(8)
C2 0.0218(10) 0.0254(10) 0.0219(11) -0.0043(9) 0.0043(8) -0.0004(8)
C3 0.0266(11) 0.0266(11) 0.0228(11) -0.0009(9) 0.0024(9) -0.0008(8)
C4 0.0229(10) 0.0267(11) 0.0280(11) -0.0018(9) 0.0016(9) -0.0005(8)
C5 0.0235(10) 0.0277(11) 0.0285(12) -0.0032(9) 0.0035(9) 0.0010(8)
C6 0.0243(10) 0.0333(12) 0.0249(11) -0.0008(9) 0.0039(9) 0.0009(9)
C7 0.0264(11) 0.0336(12) 0.0259(12) -0.0006(9) 0.0032(9) -0.0016(9)
C8 0.0279(11) 0.0255(11) 0.0298(12) -0.0018(9) -0.0030(9) 0.0013(9)
C9 0.0298(12) 0.0333(13) 0.0410(14) 0.0022(10) -0.0022(10) 0.0021(9)
C10 0.0318(13) 0.0303(13) 0.0586(17) -0.0095(12) -0.0038(12) 0.0019(10)
C11 0.0541(16) 0.0332(14) 0.0569(18) -0.0064(13) -0.0235(14) 0.0135(12)
C12 0.0736(17) 0.0361(14) 0.0313(14) 0.0013(11) -0.0134(13) 0.0092(12)
C13 0.0485(14) 0.0319(12) 0.0305(13) -0.0014(10) 0.0004(11) 0.0062(10)
C14 0.0311(13) 0.0534(17) 0.110(2) -0.0106(17) 0.0047(14) 0.0073(12)
C15 0.0272(11) 0.0278(11) 0.0272(12) -0.0014(9) 0.0058(9) -0.0018(9)
C16 0.0297(11) 0.0281(11) 0.0303(12) -0.0034(9) 0.0072(9) -0.0018(9)
C17 0.0251(11) 0.0279(11) 0.0309(12) -0.0038(9) 0.0084(9) -0.0002(8)
C18 0.0262(11) 0.0323(12) 0.0338(12) -0.0029(10) 0.0060(10) 0.0020(9)
C19 0.0369(12) 0.0295(12) 0.0348(13) -0.0042(10) 0.0123(10) -0.0032(10)
C20 0.0298(12) 0.0427(14) 0.0533(16) -0.0008(12) 0.0207(11) 0.0027(10)
C21 0.0287(12) 0.0520(15) 0.0517(16) 0.0058(13) 0.0045(11) 0.0069(10)
C22 0.0346(12) 0.0476(14) 0.0322(13) 0.0032(11) 0.0069(11) 0.0021(10)
C23 0.0626(16) 0.0627(18) 0.0444(16) 0.0023(13) 0.0247(13) -0.0052(13)
C24 0.0300(11) 0.0306(12) 0.0317(13) 0.0016(10) 0.0002(10) -0.0006(9)
C25 0.0393(13) 0.0361(13) 0.0306(13) -0.0004(10) 0.0025(10) -0.0030(10)
C26 0.0419(13) 0.0287(12) 0.0267(12) -0.0010(9) 0.0079(10) -0.0050(10)
C27 0.0355(12) 0.0344(12) 0.0290(12) 0.0002(10) 0.0062(10) -0.0055(10)
C28 0.0423(13) 0.0289(12) 0.0264(12) -0.0010(10) 0.0025(10) -0.0098(10)
C29 0.0629(15) 0.0339(13) 0.0268(13) -0.0016(10) 0.0144(12) -0.0070(11)
C30 0.0549(15) 0.0371(14) 0.0452(15) -0.0013(12) 0.0254(12) 0.0015(11)
C31 0.0462(14) 0.0316(12) 0.0420(14) 0.0041(11) 0.0084(11) 0.0066(10)
C32 0.0551(15) 0.0483(15) 0.0402(15) 0.0073(12) -0.0059(12) -0.0157(12)
C33 0.0299(11) 0.0320(12) 0.0321(12) 0.0017(10) 0.0029(10) -0.0001(9)
C34 0.0325(12) 0.0356(13) 0.0384(14) 0.0022(11) -0.0027(11) 0.0005(10)
C35 0.0308(12) 0.0319(12) 0.0363(13) 0.0011(10) -0.0011(10) 0.0056(9)
C36 0.0346(12) 0.0373(13) 0.0316(13) 0.0043(10) 0.0008(10) 0.0012(10)
C37 0.0304(12) 0.0309(12) 0.0430(15) -0.0005(11) 0.0001(11) 0.0028(9)
C38 0.0360(13) 0.0496(15) 0.0450(15) 0.0064(12) -0.0065(12) 0.0134(11)
C39 0.0525(16) 0.082(2) 0.0395(16) 0.0192(14) 0.0043(13) 0.0182(14)
C40 0.0359(13) 0.0764(19) 0.0464(16) 0.0155(14) 0.0094(12) 0.0159(13)
C41 0.0334(13) 0.0613(17) 0.0619(18) -0.0005(14) 0.0044(12) 0.0086(12)
C42 0.0251(11) 0.0360(12) 0.0317(12) -0.0017(10) 0.0031(10) 0.0043(9)
C43 0.0295(12) 0.0359(13) 0.0344(13) -0.0047(10) 0.0030(10) 0.0032(9)
C44 0.0232(11) 0.0314(12) 0.0365(13) -0.0049(10) 0.0075(10) 0.0028(9)
C45 0.0311(11) 0.0378(13) 0.0279(12) -0.0034(10) 0.0068(10) 0.0023(9)
C46 0.0248(11) 0.0288(12) 0.0378(13) -0.0116(10) 0.0044(10) 0.0000(9)
C47 0.0298(12) 0.0349(12) 0.0421(14) -0.0077(11) 0.0157(11) -0.0041(10)
C48 0.0467(14) 0.0348(13) 0.0367(13) -0.0007(11) 0.0161(11) -0.0022(11)
C49 0.0346(12) 0.0338(12) 0.0347(13) 0.0003(10) 0.0052(10) 0.0049(9)
C50 0.0297(12) 0.0436(14) 0.0488(15) -0.0130(12) 0.0003(11) 0.0027(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 117.77(17)
N1 C1 C2 123.29(17)
N1 C1 C6 117.12(17)
C2 C1 C6 119.59(17)
C3 C2 C1 118.42(17)
C3 C2 C15 120.84(18)
C1 C2 C15 120.73(17)
C2 C3 C4 118.71(18)
C2 C3 C24 120.55(17)
C4 C3 C24 120.73(17)
C5 C4 C3 118.15(17)
C5 C4 C33 121.31(18)
C3 C4 C33 120.54(18)
N1 C5 C4 123.61(17)
N1 C5 C42 115.73(18)
C4 C5 C42 120.66(17)
C7 C6 C1 175.9(2)
C6 C7 C8 177.4(2)
C13 C8 C9 119.27(18)
C13 C8 C7 121.38(19)
C9 C8 C7 119.36(19)
C10 C9 C8 121.5(2)
C10 C9 H9 119.3
C8 C9 H9 119.3
C11 C10 C9 118.1(2)
C11 C10 C14 121.9(2)
C9 C10 C14 120.0(2)
C10 C11 C12 121.6(2)
C10 C11 H11 119.2
C12 C11 H11 119.2
C11 C12 C13 120.3(2)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 119.3(2)
C12 C13 H13 120.3
C8 C13 H13 120.3
C10 C14 H14A 109.5
C10 C14 H14B 109.5
H14A C14 H14B 109.5
C10 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C2 178.9(2)
C15 C16 C17 177.9(2)
C22 C17 C18 119.06(18)
C22 C17 C16 121.49(19)
C18 C17 C16 119.43(18)
C19 C18 C17 121.49(19)
C19 C18 H18 119.3
C17 C18 H18 119.3
C20 C19 C18 118.4(2)
C20 C19 C23 120.7(2)
C18 C19 C23 121.0(2)
C19 C20 C21 121.2(2)
C19 C20 H20 119.4
C21 C20 H20 119.4
C20 C21 C22 120.4(2)
C20 C21 H21 119.8
C22 C21 H21 119.8
C21 C22 C17 119.5(2)
C21 C22 H22 120.2
C17 C22 H22 120.2
C19 C23 H23A 109.5
C19 C23 H23B 109.5
C19 C23 H23C 109.5
C19 C23 H23D 109.5
C19 C23 H23E 109.5
H23D C23 H23E 109.4
C19 C23 H23F 109.5
H23D C23 H23F 109.4
H23E C23 H23F 109.4
C25 C24 C3 178.2(2)
C24 C25 C26 178.3(2)
C27 C26 C31 119.2(2)
C27 C26 C25 120.07(19)
C31 C26 C25 120.7(2)
C28 C27 C26 122.2(2)
C28 C27 H27 118.9
C26 C27 H27 118.9
C27 C28 C29 117.6(2)
C27 C28 C32 121.6(2)
C29 C28 C32 120.8(2)
C30 C29 C28 121.2(2)
C30 C29 H29 119.4
C28 C29 H29 119.4
C29 C30 C31 120.6(2)
C29 C30 H30 119.7
C31 C30 H30 119.7
C30 C31 C26 119.2(2)
C30 C31 H31 120.4
C26 C31 H31 120.4
C28 C32 H32A 109.5
C28 C32 H32B 109.5
H32A C32 H32B 109.5
C28 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
C34 C33 C4 178.7(2)
C33 C34 C35 179.4(3)
C36 C35 C40 118.99(19)
C36 C35 C34 120.3(2)
C40 C35 C34 120.7(2)
C35 C36 C37 121.7(2)
C35 C36 H36 119.1
C37 C36 H36 119.1
C38 C37 C36 117.9(2)
C38 C37 C41 121.6(2)
C36 C37 C41 120.6(2)
C39 C38 C37 121.4(2)
C39 C38 H38 119.3
C37 C38 H38 119.3
C38 C39 C40 120.3(2)
C38 C39 H39 119.8
C40 C39 H39 119.8
C39 C40 C35 119.7(2)
C39 C40 H40 120.2
C35 C40 H40 120.2
C37 C41 H41A 109.5
C37 C41 H41B 109.5
H41A C41 H41B 109.5
C37 C41 H41C 109.5
H41A C41 H41C 109.5
H41B C41 H41C 109.5
C43 C42 C5 179.1(2)
C42 C43 C44 179.6(2)
C45 C44 C49 119.08(18)
C45 C44 C43 120.43(19)
C49 C44 C43 120.49(18)
C46 C45 C44 121.8(2)
C46 C45 H45 119.1
C44 C45 H45 119.1
C45 C46 C47 117.97(19)
C45 C46 C50 120.9(2)
C47 C46 C50 121.10(19)
C48 C47 C46 121.01(19)
C48 C47 H47 119.5
C46 C47 H47 119.5
C47 C48 C49 120.8(2)
C47 C48 H48 119.6
C49 C48 H48 119.6
C48 C49 C44 119.37(19)
C48 C49 H49 120.3
C44 C49 H49 120.3
C46 C50 H50A 109.5
C46 C50 H50B 109.5
H50A C50 H50B 109.5
C46 C50 H50C 109.5
H50A C50 H50C 109.5
H50B C50 H50C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.344(2)
N1 C5 1.347(2)
C1 C2 1.412(2)
C1 C6 1.433(3)
C2 C3 1.403(2)
C2 C15 1.425(2)
C3 C4 1.409(2)
C3 C24 1.424(3)
C4 C5 1.407(3)
C4 C33 1.423(3)
C5 C42 1.441(3)
C6 C7 1.195(2)
C7 C8 1.437(3)
C8 C13 1.392(3)
C8 C9 1.393(3)
C9 C10 1.387(3)
C9 H9 0.9500
C10 C11 1.374(3)
C10 C14 1.516(3)
C11 C12 1.381(3)
C11 H11 0.9500
C12 C13 1.384(3)
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C16 1.195(2)
C16 C17 1.440(3)
C17 C22 1.390(3)
C17 C18 1.392(3)
C18 C19 1.385(2)
C18 H18 0.9500
C19 C20 1.378(3)
C19 C23 1.504(3)
C20 C21 1.378(3)
C20 H20 0.9500
C21 C22 1.385(3)
C21 H21 0.9500
C22 H22 0.9500
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C23 H23D 0.9804
C23 H23E 0.9803
C23 H23F 0.9804
C24 C25 1.200(3)
C25 C26 1.446(3)
C26 C27 1.387(3)
C26 C31 1.390(3)
C27 C28 1.384(3)
C27 H27 0.9500
C28 C29 1.384(3)
C28 C32 1.500(3)
C29 C30 1.381(3)
C29 H29 0.9500
C30 C31 1.384(3)
C30 H30 0.9500
C31 H31 0.9500
C32 H32A 0.9800
C32 H32B 0.9800
C32 H32C 0.9800
C33 C34 1.197(3)
C34 C35 1.435(3)
C35 C36 1.388(3)
C35 C40 1.392(3)
C36 C37 1.390(3)
C36 H36 0.9500
C37 C38 1.380(3)
C37 C41 1.504(3)
C38 C39 1.378(3)
C38 H38 0.9500
C39 C40 1.380(3)
C39 H39 0.9500
C40 H40 0.9500
C41 H41A 0.9800
C41 H41B 0.9800
C41 H41C 0.9800
C42 C43 1.196(2)
C43 C44 1.440(3)
C44 C45 1.393(3)
C44 C49 1.394(3)
C45 C46 1.385(2)
C45 H45 0.9500
C46 C47 1.388(3)
C46 C50 1.504(3)
C47 C48 1.379(3)
C47 H47 0.9500
C48 C49 1.379(3)
C48 H48 0.9500
C49 H49 0.9500
C50 H50A 0.9800
C50 H50B 0.9800
C50 H50C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 C2 1.3(3)
C5 N1 C1 C6 -178.52(17)
N1 C1 C2 C3 0.1(3)
C6 C1 C2 C3 179.91(17)
N1 C1 C2 C15 179.77(17)
C6 C1 C2 C15 -0.4(3)
C1 C2 C3 C4 -1.2(3)
C15 C2 C3 C4 179.12(17)
C1 C2 C3 C24 178.41(18)
C15 C2 C3 C24 -1.3(3)
C2 C3 C4 C5 0.9(3)
C24 C3 C4 C5 -178.70(18)
C2 C3 C4 C33 -179.32(18)
C24 C3 C4 C33 1.1(3)
C1 N1 C5 C4 -1.6(3)
C1 N1 C5 C42 178.52(17)
C3 C4 C5 N1 0.5(3)
C33 C4 C5 N1 -179.24(18)
C3 C4 C5 C42 -179.62(17)
C33 C4 C5 C42 0.6(3)
N1 C1 C6 C7 135(3)
C2 C1 C6 C7 -45(3)
C1 C6 C7 C8 58(7)
C6 C7 C8 C13 167(5)
C6 C7 C8 C9 -14(5)
C13 C8 C9 C10 -1.5(3)
C7 C8 C9 C10 178.77(19)
C8 C9 C10 C11 1.6(3)
C8 C9 C10 C14 -179.2(2)
C9 C10 C11 C12 -0.5(3)
C14 C10 C11 C12 -179.7(2)
C10 C11 C12 C13 -0.7(3)
C11 C12 C13 C8 0.8(3)
C9 C8 C13 C12 0.2(3)
C7 C8 C13 C12 179.97(19)
C3 C2 C15 C16 53(11)
C1 C2 C15 C16 -127(11)
C2 C15 C16 C17 -42(15)
C15 C16 C17 C22 153(6)
C15 C16 C17 C18 -25(6)
C22 C17 C18 C19 -0.5(3)
C16 C17 C18 C19 178.08(18)
C17 C18 C19 C20 1.5(3)
C17 C18 C19 C23 -178.4(2)
C18 C19 C20 C21 -1.5(3)
C23 C19 C20 C21 178.4(2)
C19 C20 C21 C22 0.5(4)
C20 C21 C22 C17 0.6(3)
C18 C17 C22 C21 -0.6(3)
C16 C17 C22 C21 -179.16(19)
C2 C3 C24 C25 -78(8)
C4 C3 C24 C25 102(8)
C3 C24 C25 C26 -121(8)
C24 C25 C26 C27 18(8)
C24 C25 C26 C31 -159(8)
C31 C26 C27 C28 0.8(3)
C25 C26 C27 C28 -177.09(19)
C26 C27 C28 C29 -0.9(3)
C26 C27 C28 C32 178.64(19)
C27 C28 C29 C30 0.4(3)
C32 C28 C29 C30 -179.2(2)
C28 C29 C30 C31 0.2(3)
C29 C30 C31 C26 -0.3(3)
C27 C26 C31 C30 -0.2(3)
C25 C26 C31 C30 177.7(2)
C5 C4 C33 C34 -163(10)
C3 C4 C33 C34 18(10)
C4 C33 C34 C35 121(24)
C33 C34 C35 C36 36(26)
C33 C34 C35 C40 -144(26)
C40 C35 C36 C37 0.7(3)
C34 C35 C36 C37 -179.1(2)
C35 C36 C37 C38 -0.3(3)
C35 C36 C37 C41 -179.4(2)
C36 C37 C38 C39 -0.2(3)
C41 C37 C38 C39 178.9(2)
C37 C38 C39 C40 0.2(4)
C38 C39 C40 C35 0.2(4)
C36 C35 C40 C39 -0.7(4)
C34 C35 C40 C39 179.1(2)
N1 C5 C42 C43 -59(13)
C4 C5 C42 C43 121(13)
C5 C42 C43 C44 -37(55)
C42 C43 C44 C45 -86(47)
C42 C43 C44 C49 93(47)
C49 C44 C45 C46 -0.2(3)
C43 C44 C45 C46 179.00(19)
C44 C45 C46 C47 0.5(3)
C44 C45 C46 C50 179.53(19)
C45 C46 C47 C48 -0.6(3)
C50 C46 C47 C48 -179.62(18)
C46 C47 C48 C49 0.4(3)
C47 C48 C49 C44 -0.1(3)
C45 C44 C49 C48 0.0(3)
C43 C44 C49 C48 -179.21(19)
|
1501994.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501994.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501994
loop_
_publ_author_name
'Ehlers, Peter'
'Neubauer, Antje'
'Lochbrunner, Stefan'
'Villinger, Alexander'
'Langer, Peter'
_publ_section_title
;
Multiple sonogashira reactions of polychlorinated molecules. Synthesis
and photophysical properties of the first pentaalkynylpyridines.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1618
_journal_page_last 1621
_journal_paper_doi 10.1021/ol2000183
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C60 H42'
_chemical_formula_sum 'C60 H42'
_chemical_formula_weight 762.94
_chemical_name_systematic
;
?
;
_space_group_IT_number 148
_symmetry_cell_setting trigonal
_symmetry_Int_Tables_number 148
_symmetry_space_group_name_Hall '-R 3'
_symmetry_space_group_name_H-M 'R -3 :H'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_formula_units_Z 3
_cell_length_a 18.6752(12)
_cell_length_b 18.6752(12)
_cell_length_c 10.6107(9)
_cell_measurement_reflns_used 5444
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 69.683
_cell_measurement_theta_min 4.364
_cell_volume 3204.8(4)
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0182
_diffrn_reflns_av_sigmaI/netI 0.0139
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 10847
_diffrn_reflns_theta_full 29.99
_diffrn_reflns_theta_max 29.99
_diffrn_reflns_theta_min 2.30
_exptl_absorpt_coefficient_mu 0.067
_exptl_absorpt_correction_T_max 0.9763
_exptl_absorpt_correction_T_min 0.9565
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.186
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1206
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.45
_exptl_crystal_size_min 0.36
_refine_diff_density_max 0.316
_refine_diff_density_min -0.213
_refine_diff_density_rms 0.039
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 93
_refine_ls_number_reflns 2068
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.091
_refine_ls_R_factor_all 0.0502
_refine_ls_R_factor_gt 0.0418
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0877P)^2^+0.4852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1269
_refine_ls_wR_factor_ref 0.1338
_reflns_number_gt 1730
_reflns_number_total 2068
_reflns_threshold_expression >2\s(I)
_cod_data_source_file ol2000183_si_002.cif
_cod_data_source_block is_pe305
_cod_original_sg_symbol_H-M 'R -3'
_cod_database_code 1501994
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93177(4) 0.01318(5) 0.49917(7) 0.0264(2) Uani 1 1 d . . .
C2 C 0.86319(5) 0.02690(5) 0.49320(8) 0.0313(2) Uani 1 1 d . . .
C3 C 0.80709(5) 0.04000(5) 0.48059(8) 0.0333(2) Uani 1 1 d . . .
C4 C 0.74189(5) 0.05881(5) 0.46634(8) 0.0306(2) Uani 1 1 d . . .
C5 C 0.75798(5) 0.13913(5) 0.48994(9) 0.0336(2) Uani 1 1 d . . .
H5 H 0.8121 0.1804 0.5140 0.040 Uiso 1 1 calc R . .
C6 C 0.69626(5) 0.15978(6) 0.47882(9) 0.0360(2) Uani 1 1 d . . .
C7 C 0.61772(5) 0.09819(6) 0.44281(9) 0.0400(2) Uani 1 1 d . . .
H7 H 0.5748 0.1111 0.4348 0.048 Uiso 1 1 calc R . .
C8 C 0.60089(5) 0.01844(6) 0.41840(10) 0.0409(2) Uani 1 1 d . . .
H8 H 0.5468 -0.0225 0.3934 0.049 Uiso 1 1 calc R . .
C9 C 0.66251(5) -0.00198(6) 0.43023(8) 0.0349(2) Uani 1 1 d . . .
H9 H 0.6508 -0.0568 0.4139 0.042 Uiso 1 1 calc R . .
C10 C 0.71535(8) 0.24703(7) 0.50370(11) 0.0507(3) Uani 1 1 d . . .
H10A H 0.7665 0.2763 0.5528 0.076 Uiso 0.766(17) 1 calc PR A 1
H10B H 0.6698 0.2459 0.5511 0.076 Uiso 0.766(17) 1 calc PR A 1
H10C H 0.7222 0.2757 0.4234 0.076 Uiso 0.766(17) 1 calc PR A 1
H10D H 0.6725 0.2558 0.4654 0.076 Uiso 0.234(17) 1 d PR A 2
H10E H 0.7693 0.2863 0.4671 0.076 Uiso 0.234(17) 1 d PR A 2
H10F H 0.7168 0.2564 0.5950 0.076 Uiso 0.234(17) 1 d PR A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0237(3) 0.0251(4) 0.0320(4) -0.0003(3) 0.0001(3) 0.0133(3)
C2 0.0271(4) 0.0304(4) 0.0376(4) 0.0000(3) 0.0002(3) 0.0154(3)
C3 0.0306(4) 0.0354(4) 0.0379(4) 0.0019(3) 0.0017(3) 0.0195(3)
C4 0.0280(4) 0.0367(4) 0.0324(4) 0.0042(3) 0.0030(3) 0.0202(3)
C5 0.0283(4) 0.0341(4) 0.0407(5) 0.0018(3) 0.0002(3) 0.0173(3)
C6 0.0400(5) 0.0423(5) 0.0366(5) 0.0033(4) 0.0031(3) 0.0287(4)
C7 0.0335(4) 0.0537(5) 0.0442(5) 0.0074(4) 0.0034(4) 0.0303(4)
C8 0.0276(4) 0.0474(5) 0.0466(5) 0.0036(4) -0.0027(3) 0.0179(4)
C9 0.0325(4) 0.0360(4) 0.0381(5) 0.0013(3) -0.0012(3) 0.0185(3)
C10 0.0650(7) 0.0485(6) 0.0552(6) -0.0028(5) -0.0005(5) 0.0409(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 C1 C1 119.985(3) 11_666 12_546
C1 C1 C2 119.72(6) 11_666 .
C1 C1 C2 120.28(6) 12_546 .
C3 C2 C1 175.91(9) . .
C2 C3 C4 177.93(9) . .
C9 C4 C5 119.54(7) . .
C9 C4 C3 121.06(8) . .
C5 C4 C3 119.40(7) . .
C6 C5 C4 121.27(7) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C7 C6 C5 118.13(8) . .
C7 C6 C10 121.60(8) . .
C5 C6 C10 120.26(8) . .
C8 C7 C6 121.30(7) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
C7 C8 C9 120.37(8) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C4 119.39(8) . .
C8 C9 H9 120.3 . .
C4 C9 H9 120.3 . .
C6 C10 H10A 109.5 . .
C6 C10 H10B 109.5 . .
C6 C10 H10C 109.5 . .
C6 C10 H10D 109.6 . .
C6 C10 H10E 109.7 . .
H10D C10 H10E 109.3 . .
C6 C10 H10F 109.7 . .
H10D C10 H10F 109.3 . .
H10E C10 H10F 109.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.4134(7) 11_666
C1 C1 1.4134(7) 12_546
C1 C2 1.4277(10) .
C2 C3 1.1967(11) .
C3 C4 1.4341(10) .
C4 C9 1.3965(12) .
C4 C5 1.3971(11) .
C5 C6 1.3912(11) .
C5 H5 0.9500 .
C6 C7 1.3905(13) .
C6 C10 1.5069(13) .
C7 C8 1.3842(14) .
C7 H7 0.9500 .
C8 C9 1.3872(12) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C10 H10D 0.9820 .
C10 H10E 0.9819 .
C10 H10F 0.9820 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C1 C1 C2 C3 70.7(12) 11_666
C1 C1 C2 C3 -108.0(12) 12_546
C1 C2 C3 C4 -81(3) .
C2 C3 C4 C9 175(100) .
C2 C3 C4 C5 -5(3) .
C9 C4 C5 C6 0.34(13) .
C3 C4 C5 C6 -179.17(8) .
C4 C5 C6 C7 -0.30(14) .
C4 C5 C6 C10 -179.47(9) .
C5 C6 C7 C8 -0.06(14) .
C10 C6 C7 C8 179.09(9) .
C6 C7 C8 C9 0.40(15) .
C7 C8 C9 C4 -0.35(14) .
C5 C4 C9 C8 -0.01(13) .
C3 C4 C9 C8 179.49(8) .
|
1501995.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501995.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501995
loop_
_publ_author_name
'Chen, Zuliang'
'Wei, Lai'
'Zhang, Junliang'
_publ_section_title
;
Lewis acid catalyzed carbon-carbon bond cleavage of aryl oxiranyl
diketones: synthesis of cis-2,5-disubstituted 1,3-dioxolanes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1170
_journal_page_last 1173
_journal_paper_doi 10.1021/ol2000292
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C33 H24 O4'
_chemical_formula_weight 484.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 161
_symmetry_cell_setting trigonal
_symmetry_space_group_name_Hall 'R 3 -2"c'
_symmetry_space_group_name_H-M 'R 3 c :H'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 120.00
_cell_formula_units_Z 18
_cell_length_a 34.4501(4)
_cell_length_b 34.4501(4)
_cell_length_c 11.2367(3)
_cell_measurement_temperature 296(2)
_cell_volume 11549.2(4)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0316
_diffrn_reflns_av_sigmaI/netI 0.0169
_diffrn_reflns_limit_h_max 40
_diffrn_reflns_limit_h_min -40
_diffrn_reflns_limit_k_max 40
_diffrn_reflns_limit_k_min -40
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 43806
_diffrn_reflns_theta_full 25.01
_diffrn_reflns_theta_max 25.01
_diffrn_reflns_theta_min 2.05
_exptl_absorpt_coefficient_mu 0.082
_exptl_absorpt_correction_T_max 0.9843
_exptl_absorpt_correction_T_min 0.9770
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.254
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 4572
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.19
_refine_diff_density_max 0.101
_refine_diff_density_min -0.107
_refine_diff_density_rms 0.020
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.6(8)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 334
_refine_ls_number_reflns 4508
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.047
_refine_ls_R_factor_all 0.0369
_refine_ls_R_factor_gt 0.0311
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+4.9199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0683
_refine_ls_wR_factor_ref 0.0717
_reflns_number_gt 4059
_reflns_number_total 4508
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000292_si_002.cif
_cod_data_source_block z
_cod_original_sg_symbol_H-M R3c
_cod_database_code 1501995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.04836(4) 0.88495(4) 0.15385(10) 0.0506(3) Uani 1 1 d .
O2 O 0.03029(4) 0.81300(4) 0.13701(9) 0.0446(3) Uani 1 1 d .
O3 O -0.01890(4) 0.78645(5) -0.13902(10) 0.0630(4) Uani 1 1 d .
O4 O 0.08378(5) 0.84576(5) -0.13789(12) 0.0668(4) Uani 1 1 d .
C1 C 0.10339(8) 0.77846(9) -0.0899(2) 0.0809(7) Uani 1 1 d .
H1A H 0.1246 0.8034 -0.1317 0.097 Uiso 1 1 calc R
C2 C 0.10903(14) 0.74234(14) -0.0757(3) 0.1207(11) Uani 1 1 d .
H2A H 0.1344 0.7429 -0.1066 0.145 Uiso 1 1 calc R
C3 C 0.07784(16) 0.70537(14) -0.0165(3) 0.1238(12) Uani 1 1 d .
H3A H 0.0820 0.6808 -0.0076 0.149 Uiso 1 1 calc R
C4 C 0.04034(12) 0.70393(9) 0.0302(3) 0.1081(10) Uani 1 1 d .
H4A H 0.0189 0.6784 0.0695 0.130 Uiso 1 1 calc R
C5 C 0.03479(9) 0.74081(7) 0.0182(2) 0.0754(6) Uani 1 1 d .
H5A H 0.0098 0.7404 0.0512 0.090 Uiso 1 1 calc R
C6 C 0.06622(7) 0.77821(6) -0.04252(15) 0.0545(4) Uani 1 1 d .
C7 C -0.09894(6) 0.75491(7) -0.01827(18) 0.0622(5) Uani 1 1 d .
H7A H -0.0991 0.7406 -0.0886 0.075 Uiso 1 1 calc R
C8 C -0.13881(7) 0.74370(8) 0.0368(2) 0.0787(6) Uani 1 1 d .
H8A H -0.1657 0.7213 0.0049 0.094 Uiso 1 1 calc R
C9 C -0.13901(7) 0.76555(8) 0.1392(2) 0.0744(6) Uani 1 1 d .
H9A H -0.1660 0.7585 0.1754 0.089 Uiso 1 1 calc R
C10 C -0.09938(7) 0.79770(7) 0.18760(19) 0.0631(5) Uani 1 1 d .
H10A H -0.0995 0.8123 0.2570 0.076 Uiso 1 1 calc R
C11 C -0.05930(6) 0.80843(5) 0.13398(15) 0.0489(4) Uani 1 1 d .
H11A H -0.0325 0.8300 0.1681 0.059 Uiso 1 1 calc R
C12 C -0.05847(5) 0.78736(5) 0.02978(14) 0.0433(4) Uani 1 1 d .
C13 C 0.02230(7) 0.89795(6) -0.15686(16) 0.0574(5) Uani 1 1 d .
H13A H 0.0386 0.8876 -0.1990 0.069 Uiso 1 1 calc R
C14 C -0.00124(8) 0.91433(7) -0.21755(18) 0.0697(6) Uani 1 1 d .
H14A H -0.0008 0.9149 -0.3003 0.084 Uiso 1 1 calc R
C15 C -0.02520(7) 0.92978(7) -0.1567(2) 0.0691(6) Uani 1 1 d .
H15A H -0.0414 0.9405 -0.1978 0.083 Uiso 1 1 calc R
C16 C -0.02521(7) 0.92934(7) -0.0352(2) 0.0692(6) Uani 1 1 d .
H16A H -0.0412 0.9401 0.0064 0.083 Uiso 1 1 calc R
C17 C -0.00173(7) 0.91301(6) 0.02626(18) 0.0580(5) Uani 1 1 d .
H17A H -0.0018 0.9130 0.1090 0.070 Uiso 1 1 calc R
C18 C 0.02186(5) 0.89670(5) -0.03423(14) 0.0440(4) Uani 1 1 d .
C19 C 0.03020(5) 0.82653(5) 0.01748(13) 0.0415(4) Uani 1 1 d .
C20 C 0.04791(5) 0.87844(5) 0.02849(14) 0.0449(4) Uani 1 1 d .
H20A H 0.0789 0.8947 -0.0003 0.054 Uiso 1 1 calc R
C21 C 0.05792(6) 0.85329(5) 0.20332(14) 0.0475(4) Uani 1 1 d .
H21A H 0.0897 0.8628 0.1922 0.057 Uiso 1 1 calc R
C22 C 0.04566(6) 0.84468(6) 0.33249(15) 0.0495(4) Uani 1 1 d .
C23 C 0.02136(7) 0.86133(6) 0.38556(16) 0.0602(5) Uani 1 1 d .
H23A H 0.0129 0.8787 0.3414 0.072 Uiso 1 1 calc R
C24 C 0.00899(8) 0.85255(7) 0.50563(19) 0.0773(6) Uani 1 1 d .
H24A H -0.0077 0.8640 0.5402 0.093 Uiso 1 1 calc R
C25 C 0.02093(9) 0.82800(9) 0.57036(18) 0.0805(7) Uani 1 1 d .
H25A H 0.0127 0.8229 0.6502 0.097 Uiso 1 1 calc R
C26 C 0.04553(7) 0.80968(8) 0.52140(17) 0.0704(6) Uani 1 1 d .
C27 C 0.05829(6) 0.81769(7) 0.39910(16) 0.0581(5) Uani 1 1 d .
C28 C 0.08167(8) 0.79785(9) 0.3497(2) 0.0840(7) Uani 1 1 d .
H28A H 0.0906 0.8032 0.2704 0.101 Uiso 1 1 calc R
C29 C 0.09135(10) 0.77094(13) 0.4168(3) 0.1240(12) Uani 1 1 d .
H29A H 0.1067 0.7578 0.3834 0.149 Uiso 1 1 calc R
C30 C 0.07809(12) 0.76298(13) 0.5378(3) 0.1318(13) Uani 1 1 d .
H30A H 0.0845 0.7443 0.5831 0.158 Uiso 1 1 calc R
C31 C 0.05668(10) 0.78187(12) 0.5875(3) 0.1061(10) Uani 1 1 d .
H31A H 0.0489 0.7766 0.6675 0.127 Uiso 1 1 calc R
C32 C -0.01694(6) 0.79883(5) -0.03737(14) 0.0436(4) Uani 1 1 d .
C33 C 0.06230(6) 0.81848(6) -0.06197(14) 0.0481(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0655(8) 0.0459(6) 0.0365(6) -0.0031(5) -0.0018(5) 0.0250(6)
O2 0.0550(7) 0.0464(6) 0.0341(5) 0.0015(5) 0.0007(5) 0.0266(6)
O3 0.0608(8) 0.0860(9) 0.0387(7) -0.0131(6) -0.0018(6) 0.0342(7)
O4 0.0729(9) 0.0707(8) 0.0559(8) 0.0096(7) 0.0254(7) 0.0353(7)
C1 0.0859(15) 0.1083(19) 0.0774(15) -0.0011(13) 0.0118(12) 0.0703(15)
C2 0.152(3) 0.167(3) 0.117(2) -0.007(2) 0.012(2) 0.135(3)
C3 0.207(4) 0.132(3) 0.108(2) -0.007(2) -0.002(3) 0.141(3)
C4 0.169(3) 0.0836(18) 0.100(2) 0.0064(15) 0.014(2) 0.085(2)
C5 0.0982(16) 0.0649(13) 0.0774(15) -0.0034(11) 0.0089(12) 0.0516(13)
C6 0.0663(12) 0.0652(12) 0.0438(10) -0.0073(9) -0.0009(8) 0.0417(10)
C7 0.0577(12) 0.0682(12) 0.0518(11) -0.0065(9) 0.0019(9) 0.0248(10)
C8 0.0461(11) 0.0896(16) 0.0793(16) -0.0037(13) 0.0011(10) 0.0181(11)
C9 0.0542(12) 0.0821(15) 0.0818(15) 0.0083(12) 0.0225(11) 0.0304(12)
C10 0.0655(12) 0.0582(11) 0.0640(12) 0.0032(9) 0.0214(10) 0.0296(10)
C11 0.0520(10) 0.0418(9) 0.0493(9) 0.0019(7) 0.0084(8) 0.0208(8)
C12 0.0461(9) 0.0411(9) 0.0423(9) 0.0066(7) 0.0041(7) 0.0215(7)
C13 0.0735(12) 0.0581(11) 0.0472(10) 0.0006(8) 0.0018(9) 0.0378(10)
C14 0.0985(17) 0.0657(12) 0.0543(12) -0.0013(10) -0.0145(11) 0.0481(13)
C15 0.0708(13) 0.0542(11) 0.0861(15) 0.0073(11) -0.0129(11) 0.0341(10)
C16 0.0699(13) 0.0555(11) 0.0927(17) 0.0130(11) 0.0199(11) 0.0392(10)
C17 0.0716(12) 0.0494(10) 0.0552(11) 0.0075(8) 0.0161(9) 0.0318(10)
C18 0.0469(9) 0.0365(8) 0.0431(10) 0.0024(7) 0.0037(7) 0.0168(7)
C19 0.0491(9) 0.0470(9) 0.0306(8) 0.0016(6) 0.0035(7) 0.0256(7)
C20 0.0489(9) 0.0454(9) 0.0358(8) 0.0018(7) 0.0050(7) 0.0201(8)
C21 0.0465(9) 0.0502(10) 0.0400(9) -0.0019(7) -0.0032(7) 0.0197(8)
C22 0.0446(9) 0.0522(10) 0.0402(9) -0.0028(8) -0.0059(7) 0.0154(8)
C23 0.0735(12) 0.0618(11) 0.0421(10) -0.0076(8) -0.0001(9) 0.0315(10)
C24 0.1035(17) 0.0772(14) 0.0466(12) -0.0069(11) 0.0101(11) 0.0418(14)
C25 0.0933(17) 0.0894(16) 0.0366(10) -0.0051(10) 0.0063(10) 0.0291(14)
C26 0.0662(13) 0.0781(14) 0.0458(11) 0.0077(10) -0.0149(10) 0.0203(11)
C27 0.0452(10) 0.0703(12) 0.0482(10) 0.0038(9) -0.0081(8) 0.0208(9)
C28 0.0680(14) 0.121(2) 0.0791(15) 0.0307(14) 0.0090(11) 0.0593(15)
C29 0.111(2) 0.180(3) 0.128(3) 0.059(2) 0.021(2) 0.107(3)
C30 0.129(3) 0.182(4) 0.115(3) 0.074(2) 0.008(2) 0.101(3)
C31 0.100(2) 0.144(3) 0.0708(16) 0.0351(17) -0.0073(15) 0.058(2)
C32 0.0536(10) 0.0440(9) 0.0356(9) 0.0004(7) 0.0012(7) 0.0261(8)
C33 0.0467(9) 0.0581(10) 0.0392(9) -0.0028(8) 0.0016(7) 0.0259(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C21 O1 C20 104.93(12)
C19 O2 C21 106.36(11)
C2 C1 C6 120.2(3)
C2 C1 H1A 119.9
C6 C1 H1A 119.9
C3 C2 C1 120.4(3)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
C2 C3 C4 120.6(3)
C2 C3 H3A 119.7
C4 C3 H3A 119.7
C3 C4 C5 119.3(3)
C3 C4 H4A 120.3
C5 C4 H4A 120.3
C6 C5 C4 120.1(2)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C1 119.3(2)
C5 C6 C33 123.57(17)
C1 C6 C33 117.17(19)
C8 C7 C12 120.77(19)
C8 C7 H7A 119.6
C12 C7 H7A 119.6
C7 C8 C9 120.0(2)
C7 C8 H8A 120.0
C9 C8 H8A 120.0
C10 C9 C8 119.94(19)
C10 C9 H9A 120.0
C8 C9 H9A 120.0
C9 C10 C11 120.24(19)
C9 C10 H10A 119.9
C11 C10 H10A 119.9
C10 C11 C12 120.65(18)
C10 C11 H11A 119.7
C12 C11 H11A 119.7
C11 C12 C7 118.37(16)
C11 C12 C32 124.01(15)
C7 C12 C32 117.56(15)
C14 C13 C18 120.53(18)
C14 C13 H13A 119.7
C18 C13 H13A 119.7
C15 C14 C13 120.36(19)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C16 C15 C14 119.5(2)
C16 C15 H15A 120.3
C14 C15 H15A 120.3
C15 C16 C17 120.5(2)
C15 C16 H16A 119.7
C17 C16 H16A 119.7
C18 C17 C16 120.36(19)
C18 C17 H17A 119.8
C16 C17 H17A 119.8
C17 C18 C13 118.71(17)
C17 C18 C20 122.47(15)
C13 C18 C20 118.81(15)
O2 C19 C32 110.41(13)
O2 C19 C33 111.52(13)
C32 C19 C33 106.49(13)
O2 C19 C20 103.55(12)
C32 C19 C20 115.02(13)
C33 C19 C20 109.96(13)
O1 C20 C18 111.03(13)
O1 C20 C19 102.90(12)
C18 C20 C19 117.61(13)
O1 C20 H20A 108.3
C18 C20 H20A 108.3
C19 C20 H20A 108.3
O1 C21 O2 104.24(12)
O1 C21 C22 112.66(14)
O2 C21 C22 109.00(13)
O1 C21 H21A 110.3
O2 C21 H21A 110.3
C22 C21 H21A 110.3
C23 C22 C27 119.82(17)
C23 C22 C21 120.70(16)
C27 C22 C21 119.44(16)
C22 C23 C24 120.9(2)
C22 C23 H23A 119.5
C24 C23 H23A 119.5
C25 C24 C23 120.5(2)
C25 C24 H24A 119.8
C23 C24 H24A 119.8
C24 C25 C26 121.5(2)
C24 C25 H25A 119.2
C26 C25 H25A 119.2
C25 C26 C31 122.2(2)
C25 C26 C27 119.3(2)
C31 C26 C27 118.5(2)
C28 C27 C22 123.20(18)
C28 C27 C26 118.9(2)
C22 C27 C26 117.93(19)
C29 C28 C27 120.5(2)
C29 C28 H28A 119.7
C27 C28 H28A 119.7
C28 C29 C30 120.0(3)
C28 C29 H29A 120.0
C30 C29 H29A 120.0
C31 C30 C29 120.9(3)
C31 C30 H30A 119.6
C29 C30 H30A 119.6
C30 C31 C26 121.3(3)
C30 C31 H31A 119.3
C26 C31 H31A 119.3
O3 C32 C12 120.63(15)
O3 C32 C19 116.84(14)
C12 C32 C19 122.54(13)
O4 C33 C6 121.78(16)
O4 C33 C19 118.78(15)
C6 C33 C19 119.44(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C21 1.402(2)
O1 C20 1.4252(18)
O2 C19 1.4223(18)
O2 C21 1.4377(19)
O3 C32 1.2093(19)
O4 C33 1.209(2)
C1 C2 1.362(4)
C1 C6 1.383(3)
C1 H1A 0.9300
C2 C3 1.360(5)
C2 H2A 0.9300
C3 C4 1.372(5)
C3 H3A 0.9300
C4 C5 1.383(3)
C4 H4A 0.9300
C5 C6 1.380(3)
C5 H5A 0.9300
C6 C33 1.476(2)
C7 C8 1.374(3)
C7 C12 1.388(3)
C7 H7A 0.9300
C8 C9 1.376(3)
C8 H8A 0.9300
C9 C10 1.369(3)
C9 H9A 0.9300
C10 C11 1.377(3)
C10 H10A 0.9300
C11 C12 1.385(2)
C11 H11A 0.9300
C12 C32 1.485(2)
C13 C14 1.378(3)
C13 C18 1.379(2)
C13 H13A 0.9300
C14 C15 1.368(3)
C14 H14A 0.9300
C15 C16 1.366(3)
C15 H15A 0.9300
C16 C17 1.380(3)
C16 H16A 0.9300
C17 C18 1.376(2)
C17 H17A 0.9300
C18 C20 1.504(2)
C19 C32 1.542(2)
C19 C33 1.550(2)
C19 C20 1.579(2)
C20 H20A 0.9800
C21 C22 1.499(2)
C21 H21A 0.9800
C22 C23 1.366(3)
C22 C27 1.421(3)
C23 C24 1.402(3)
C23 H23A 0.9300
C24 C25 1.327(3)
C24 H24A 0.9300
C25 C26 1.398(3)
C25 H25A 0.9300
C26 C31 1.409(4)
C26 C27 1.427(3)
C27 C28 1.405(3)
C28 C29 1.360(3)
C28 H28A 0.9300
C29 C30 1.417(5)
C29 H29A 0.9300
C30 C31 1.326(5)
C30 H30A 0.9300
C31 H31A 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.1(5)
C1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 -1.0(5)
C3 C4 C5 C6 1.5(4)
C4 C5 C6 C1 -0.7(3)
C4 C5 C6 C33 178.4(2)
C2 C1 C6 C5 -0.6(4)
C2 C1 C6 C33 -179.8(2)
C12 C7 C8 C9 1.7(3)
C7 C8 C9 C10 -1.6(4)
C8 C9 C10 C11 0.3(3)
C9 C10 C11 C12 0.8(3)
C10 C11 C12 C7 -0.7(3)
C10 C11 C12 C32 176.27(16)
C8 C7 C12 C11 -0.6(3)
C8 C7 C12 C32 -177.75(19)
C18 C13 C14 C15 0.3(3)
C13 C14 C15 C16 0.8(3)
C14 C15 C16 C17 -0.7(3)
C15 C16 C17 C18 -0.4(3)
C16 C17 C18 C13 1.4(3)
C16 C17 C18 C20 -179.86(16)
C14 C13 C18 C17 -1.4(3)
C14 C13 C18 C20 179.84(17)
C21 O2 C19 C32 -140.14(13)
C21 O2 C19 C33 101.68(15)
C21 O2 C19 C20 -16.51(15)
C21 O1 C20 C18 158.64(13)
C21 O1 C20 C19 31.95(15)
C17 C18 C20 O1 -6.1(2)
C13 C18 C20 O1 172.58(14)
C17 C18 C20 C19 111.96(18)
C13 C18 C20 C19 -69.3(2)
O2 C19 C20 O1 -9.10(15)
C32 C19 C20 O1 111.45(14)
C33 C19 C20 O1 -128.37(13)
O2 C19 C20 C18 -131.46(13)
C32 C19 C20 C18 -10.92(19)
C33 C19 C20 C18 109.27(15)
C20 O1 C21 O2 -43.68(15)
C20 O1 C21 C22 -161.72(13)
C19 O2 C21 O1 37.44(16)
C19 O2 C21 C22 157.96(14)
O1 C21 C22 C23 9.8(2)
O2 C21 C22 C23 -105.44(18)
O1 C21 C22 C27 -172.29(14)
O2 C21 C22 C27 72.52(19)
C27 C22 C23 C24 0.6(3)
C21 C22 C23 C24 178.60(18)
C22 C23 C24 C25 0.4(3)
C23 C24 C25 C26 -0.8(4)
C24 C25 C26 C31 -177.0(2)
C24 C25 C26 C27 0.3(3)
C23 C22 C27 C28 177.3(2)
C21 C22 C27 C28 -0.7(3)
C23 C22 C27 C26 -1.2(3)
C21 C22 C27 C26 -179.15(16)
C25 C26 C27 C28 -177.8(2)
C31 C26 C27 C28 -0.4(3)
C25 C26 C27 C22 0.7(3)
C31 C26 C27 C22 178.1(2)
C22 C27 C28 C29 -177.5(2)
C26 C27 C28 C29 1.0(4)
C27 C28 C29 C30 -0.4(5)
C28 C29 C30 C31 -0.8(6)
C29 C30 C31 C26 1.3(6)
C25 C26 C31 C30 176.6(3)
C27 C26 C31 C30 -0.7(4)
C11 C12 C32 O3 -164.09(17)
C7 C12 C32 O3 12.9(2)
C11 C12 C32 C19 16.1(2)
C7 C12 C32 C19 -166.90(16)
O2 C19 C32 O3 -138.66(14)
C33 C19 C32 O3 -17.4(2)
C20 C19 C32 O3 104.64(17)
O2 C19 C32 C12 41.2(2)
C33 C19 C32 C12 162.37(14)
C20 C19 C32 C12 -75.55(18)
C5 C6 C33 O4 -161.8(2)
C1 C6 C33 O4 17.3(3)
C5 C6 C33 C19 18.8(3)
C1 C6 C33 C19 -162.11(18)
O2 C19 C33 O4 -142.10(16)
C32 C19 C33 O4 97.39(18)
C20 C19 C33 O4 -27.8(2)
O2 C19 C33 C6 37.3(2)
C32 C19 C33 C6 -83.21(17)
C20 C19 C33 C6 151.57(15)
|
1501996.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501996.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501996
loop_
_publ_author_name
'Chen, Zuliang'
'Wei, Lai'
'Zhang, Junliang'
_publ_section_title
;
Lewis acid catalyzed carbon-carbon bond cleavage of aryl oxiranyl
diketones: synthesis of cis-2,5-disubstituted 1,3-dioxolanes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1170
_journal_page_last 1173
_journal_paper_doi 10.1021/ol2000292
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C20 H20 O5'
_chemical_formula_weight 340.36
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 100.077(5)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 10.333(2)
_cell_length_b 8.0719(16)
_cell_length_c 21.608(4)
_cell_measurement_temperature 173(2)
_cell_volume 1774.5(6)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0607
_diffrn_reflns_av_sigmaI/netI 0.0381
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_number 17884
_diffrn_reflns_theta_full 25.01
_diffrn_reflns_theta_max 25.01
_diffrn_reflns_theta_min 1.91
_exptl_absorpt_coefficient_mu 0.091
_exptl_absorpt_correction_T_max 0.9723
_exptl_absorpt_correction_T_min 0.9575
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.274
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 720
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.33
_exptl_crystal_size_min 0.31
_refine_diff_density_max 0.378
_refine_diff_density_min -0.281
_refine_diff_density_rms 0.049
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 226
_refine_ls_number_reflns 3105
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.083
_refine_ls_R_factor_all 0.0580
_refine_ls_R_factor_gt 0.0467
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.6569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1305
_refine_ls_wR_factor_ref 0.1401
_reflns_number_gt 2481
_reflns_number_total 3105
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000292_si_003.cif
_cod_data_source_block z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1774.4(6)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1501996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.22572(13) 0.29987(15) 0.42061(6) 0.0283(3) Uani 1 1 d .
O2 O 0.13229(13) 0.08951(15) 0.46574(6) 0.0263(3) Uani 1 1 d .
O3 O 0.42225(14) 0.46032(18) 0.55368(6) 0.0362(4) Uani 1 1 d .
O4 O 0.13614(15) 0.56740(17) 0.53664(7) 0.0393(4) Uani 1 1 d .
O5 O 0.41164(15) -0.0801(2) 0.74301(6) 0.0428(4) Uani 1 1 d .
C1 C 0.34752(19) -0.0010(3) 0.68983(9) 0.0321(5) Uani 1 1 d .
C2 C 0.3098(2) 0.1651(3) 0.68718(9) 0.0342(5) Uani 1 1 d .
H2A H 0.3272 0.2322 0.7238 0.041 Uiso 1 1 calc R
C3 C 0.24629(19) 0.2321(2) 0.63019(9) 0.0309(5) Uani 1 1 d .
H3A H 0.2204 0.3452 0.6286 0.037 Uiso 1 1 calc R
C4 C 0.22014(18) 0.1366(2) 0.57578(8) 0.0244(4) Uani 1 1 d .
C5 C 0.25684(19) -0.0312(2) 0.57967(9) 0.0293(5) Uani 1 1 d .
H5A H 0.2385 -0.0989 0.5432 0.035 Uiso 1 1 calc R
C6 C 0.3194(2) -0.0996(3) 0.63589(9) 0.0332(5) Uani 1 1 d .
H6A H 0.3431 -0.2134 0.6378 0.040 Uiso 1 1 calc R
C7 C 0.13839(19) 0.0672(2) 0.35496(8) 0.0266(4) Uani 1 1 d .
C8 C 0.0281(2) -0.0127(3) 0.32217(9) 0.0326(5) Uani 1 1 d .
H8A H -0.0558 0.0078 0.3329 0.039 Uiso 1 1 calc R
C9 C 0.0397(2) -0.1224(3) 0.27369(11) 0.0453(6) Uani 1 1 d .
H9A H -0.0359 -0.1773 0.2517 0.054 Uiso 1 1 calc R
C10 C 0.1617(2) -0.1512(3) 0.25770(11) 0.0503(6) Uani 1 1 d .
H10A H 0.1696 -0.2246 0.2242 0.060 Uiso 1 1 calc R
C11 C 0.2727(2) -0.0729(3) 0.29047(12) 0.0513(7) Uani 1 1 d .
H11A H 0.3564 -0.0943 0.2798 0.062 Uiso 1 1 calc R
C12 C 0.2614(2) 0.0367(3) 0.33891(10) 0.0391(5) Uani 1 1 d .
H12A H 0.3373 0.0907 0.3611 0.047 Uiso 1 1 calc R
C13 C 0.15334(18) 0.2121(2) 0.51428(8) 0.0250(4) Uani 1 1 d .
H13A H 0.0665 0.2587 0.5199 0.030 Uiso 1 1 calc R
C14 C 0.23367(18) 0.3512(2) 0.48468(8) 0.0253(4) Uani 1 1 d .
C15 C 0.12145(18) 0.1793(2) 0.40849(8) 0.0252(4) Uani 1 1 d .
H15A H 0.0344 0.2365 0.3991 0.030 Uiso 1 1 calc R
C16 C 0.38018(19) 0.3527(2) 0.51633(9) 0.0289(4) Uani 1 1 d .
C17 C 0.4641(2) 0.2133(3) 0.49931(12) 0.0446(6) Uani 1 1 d .
H17A H 0.5543 0.2268 0.5220 0.067 Uiso 1 1 calc R
H17B H 0.4639 0.2151 0.4539 0.067 Uiso 1 1 calc R
H17C H 0.4288 0.1074 0.5109 0.067 Uiso 1 1 calc R
C18 C 0.17492(19) 0.5259(2) 0.48902(9) 0.0292(4) Uani 1 1 d .
C19 C 0.1701(2) 0.6365(3) 0.43291(10) 0.0406(5) Uani 1 1 d .
H19A H 0.1311 0.7432 0.4411 0.061 Uiso 1 1 calc R
H19B H 0.1166 0.5843 0.3962 0.061 Uiso 1 1 calc R
H19C H 0.2594 0.6544 0.4248 0.061 Uiso 1 1 calc R
C20 C 0.4206(3) 0.0063(4) 0.80145(10) 0.0568(7) Uani 1 1 d .
H20A H 0.4680 -0.0622 0.8355 0.085 Uiso 1 1 calc R
H20B H 0.3320 0.0295 0.8096 0.085 Uiso 1 1 calc R
H20C H 0.4679 0.1108 0.7993 0.085 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0376(8) 0.0200(7) 0.0280(7) -0.0012(5) 0.0072(6) -0.0038(6)
O2 0.0339(7) 0.0201(7) 0.0241(6) 0.0001(5) 0.0030(5) -0.0039(5)
O3 0.0381(8) 0.0348(8) 0.0341(8) -0.0010(6) 0.0023(6) -0.0102(7)
O4 0.0527(10) 0.0261(8) 0.0388(8) -0.0058(6) 0.0067(7) 0.0084(7)
O5 0.0444(9) 0.0492(10) 0.0310(8) 0.0129(7) -0.0039(6) -0.0009(7)
C1 0.0285(10) 0.0378(12) 0.0290(10) 0.0090(9) 0.0020(8) -0.0051(9)
C2 0.0404(12) 0.0345(12) 0.0264(10) -0.0026(8) 0.0019(8) -0.0108(9)
C3 0.0381(11) 0.0228(10) 0.0312(10) -0.0005(8) 0.0050(8) -0.0027(9)
C4 0.0267(10) 0.0211(10) 0.0258(9) 0.0017(7) 0.0057(7) -0.0021(8)
C5 0.0362(11) 0.0233(10) 0.0283(10) -0.0005(8) 0.0054(8) 0.0010(8)
C6 0.0358(11) 0.0275(11) 0.0364(11) 0.0066(9) 0.0067(9) 0.0039(9)
C7 0.0328(10) 0.0201(9) 0.0267(9) 0.0034(7) 0.0041(8) 0.0018(8)
C8 0.0307(11) 0.0308(11) 0.0356(11) -0.0041(9) 0.0041(9) 0.0020(9)
C9 0.0435(13) 0.0437(14) 0.0463(13) -0.0183(11) 0.0008(10) -0.0037(11)
C10 0.0554(15) 0.0473(15) 0.0509(14) -0.0259(12) 0.0171(12) -0.0047(12)
C11 0.0435(14) 0.0508(15) 0.0653(16) -0.0229(12) 0.0256(12) -0.0048(11)
C12 0.0327(12) 0.0364(12) 0.0493(13) -0.0140(10) 0.0099(10) -0.0056(9)
C13 0.0260(9) 0.0218(10) 0.0270(10) -0.0018(7) 0.0042(8) 0.0010(8)
C14 0.0312(10) 0.0192(10) 0.0248(9) -0.0003(7) 0.0030(8) 0.0009(8)
C15 0.0275(10) 0.0223(10) 0.0254(9) 0.0026(7) 0.0031(8) 0.0008(8)
C16 0.0328(11) 0.0200(10) 0.0332(10) 0.0063(8) 0.0037(8) -0.0025(8)
C17 0.0313(12) 0.0286(12) 0.0727(16) -0.0007(11) 0.0055(11) 0.0026(9)
C18 0.0301(11) 0.0227(10) 0.0321(10) -0.0031(8) -0.0023(8) 0.0005(8)
C19 0.0533(14) 0.0217(11) 0.0452(12) 0.0054(9) 0.0043(10) 0.0064(10)
C20 0.0633(17) 0.0729(18) 0.0292(12) 0.0089(12) -0.0056(11) -0.0075(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 O1 C15 106.58(13)
C15 O2 C13 105.30(13)
C1 O5 C20 117.21(18)
O5 C1 C2 124.71(19)
O5 C1 C6 115.49(19)
C2 C1 C6 119.79(18)
C1 C2 C3 119.51(18)
C1 C2 H2A 120.2
C3 C2 H2A 120.2
C4 C3 C2 121.41(19)
C4 C3 H3A 119.3
C2 C3 H3A 119.3
C3 C4 C5 118.21(17)
C3 C4 C13 120.63(17)
C5 C4 C13 121.15(16)
C6 C5 C4 121.04(18)
C6 C5 H5A 119.5
C4 C5 H5A 119.5
C5 C6 C1 120.01(19)
C5 C6 H6A 120.0
C1 C6 H6A 120.0
C8 C7 C12 119.50(18)
C8 C7 C15 118.40(17)
C12 C7 C15 122.05(17)
C7 C8 C9 120.44(19)
C7 C8 H8A 119.8
C9 C8 H8A 119.8
C10 C9 C8 119.8(2)
C10 C9 H9A 120.1
C8 C9 H9A 120.1
C9 C10 C11 120.2(2)
C9 C10 H10A 119.9
C11 C10 H10A 119.9
C10 C11 C12 120.2(2)
C10 C11 H11A 119.9
C12 C11 H11A 119.9
C11 C12 C7 119.9(2)
C11 C12 H12A 120.1
C7 C12 H12A 120.1
O2 C13 C4 110.63(15)
O2 C13 C14 102.47(13)
C4 C13 C14 116.49(15)
O2 C13 H13A 109.0
C4 C13 H13A 109.0
C14 C13 H13A 109.0
O1 C14 C18 111.47(15)
O1 C14 C16 108.37(14)
C18 C14 C16 109.31(15)
O1 C14 C13 103.76(14)
C18 C14 C13 112.36(15)
C16 C14 C13 111.42(14)
O2 C15 O1 104.10(13)
O2 C15 C7 111.13(14)
O1 C15 C7 111.25(14)
O2 C15 H15A 110.1
O1 C15 H15A 110.1
C7 C15 H15A 110.1
O3 C16 C17 122.90(18)
O3 C16 C14 120.53(17)
C17 C16 C14 116.56(17)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O4 C18 C19 123.46(18)
O4 C18 C14 119.65(17)
C19 C18 C14 116.89(16)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
O5 C20 H20A 109.5
O5 C20 H20B 109.5
H20A C20 H20B 109.5
O5 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C14 1.434(2)
O1 C15 1.441(2)
O2 C15 1.421(2)
O2 C13 1.431(2)
O3 C16 1.214(2)
O4 C18 1.215(2)
O5 C1 1.379(2)
O5 C20 1.431(3)
C1 C2 1.394(3)
C1 C6 1.399(3)
C2 C3 1.399(3)
C2 H2A 0.9500
C3 C4 1.392(3)
C3 H3A 0.9500
C4 C5 1.405(3)
C4 C13 1.514(2)
C5 C6 1.387(3)
C5 H5A 0.9500
C6 H6A 0.9500
C7 C8 1.391(3)
C7 C12 1.397(3)
C7 C15 1.503(3)
C8 C9 1.393(3)
C8 H8A 0.9500
C9 C10 1.384(3)
C9 H9A 0.9500
C10 C11 1.389(3)
C10 H10A 0.9500
C11 C12 1.391(3)
C11 H11A 0.9500
C12 H12A 0.9500
C13 C14 1.595(3)
C13 H13A 1.0000
C14 C18 1.544(3)
C14 C16 1.548(3)
C15 H15A 1.0000
C16 C17 1.504(3)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.500(3)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C20 O5 C1 C2 10.8(3)
C20 O5 C1 C6 -168.68(19)
O5 C1 C2 C3 179.37(18)
C6 C1 C2 C3 -1.2(3)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 1.3(3)
C2 C3 C4 C13 -178.94(17)
C3 C4 C5 C6 -1.0(3)
C13 C4 C5 C6 179.24(17)
C4 C5 C6 C1 -0.3(3)
O5 C1 C6 C5 -179.03(17)
C2 C1 C6 C5 1.5(3)
C12 C7 C8 C9 0.0(3)
C15 C7 C8 C9 -177.68(19)
C7 C8 C9 C10 -0.5(3)
C8 C9 C10 C11 1.0(4)
C9 C10 C11 C12 -1.0(4)
C10 C11 C12 C7 0.5(4)
C8 C7 C12 C11 0.0(3)
C15 C7 C12 C11 177.6(2)
C15 O2 C13 C4 -156.94(14)
C15 O2 C13 C14 -32.10(16)
C3 C4 C13 O2 -177.78(15)
C5 C4 C13 O2 1.9(2)
C3 C4 C13 C14 65.8(2)
C5 C4 C13 C14 -114.51(19)
C15 O1 C14 C18 -105.18(16)
C15 O1 C14 C16 134.49(14)
C15 O1 C14 C13 15.97(17)
O2 C13 C14 O1 9.67(17)
C4 C13 C14 O1 130.55(16)
O2 C13 C14 C18 130.21(15)
C4 C13 C14 C18 -108.90(18)
O2 C13 C14 C16 -106.73(16)
C4 C13 C14 C16 14.2(2)
C13 O2 C15 O1 43.60(16)
C13 O2 C15 C7 163.46(15)
C14 O1 C15 O2 -36.73(17)
C14 O1 C15 C7 -156.50(14)
C8 C7 C15 O2 87.8(2)
C12 C7 C15 O2 -89.9(2)
C8 C7 C15 O1 -156.72(16)
C12 C7 C15 O1 25.6(2)
O1 C14 C16 O3 141.82(17)
C18 C14 C16 O3 20.2(2)
C13 C14 C16 O3 -104.64(19)
O1 C14 C16 C17 -39.5(2)
C18 C14 C16 C17 -161.17(17)
C13 C14 C16 C17 74.0(2)
O1 C14 C18 O4 157.08(17)
C16 C14 C18 O4 -83.1(2)
C13 C14 C18 O4 41.1(2)
O1 C14 C18 C19 -23.3(2)
C16 C14 C18 C19 96.48(19)
C13 C14 C18 C19 -139.28(17)
|
1501997.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501997.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501997
loop_
_publ_author_name
'de Silva, E. Dilip'
'Williams, David E.'
'Jayanetti, Dinith R.'
'Centko, Ryan M.'
'Patrick, Brian O.'
'Wijesundera, Ravi L. C.'
'Andersen, Raymond J.'
_publ_section_title
;
Dhilirolides A-D, meroterpenoids produced in culture by the
fruit-infecting fungus Penicillium purpurogenum collected in Sri Lanka.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1174
_journal_page_last 1177
_journal_paper_doi 10.1021/ol200031t
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_sum 'C25 H28 O9'
_chemical_formula_weight 472.47
_chemical_name_systematic
;
?
;
_space_group_IT_number 1
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall 'P 1'
_symmetry_space_group_name_H-M 'P 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 65.339(2)
_cell_angle_beta 65.488(2)
_cell_angle_gamma 64.504(2)
_cell_formula_units_Z 4
_cell_length_a 13.5779(5)
_cell_length_b 13.6410(5)
_cell_length_c 15.0542(6)
_cell_measurement_reflns_used 9179
_cell_measurement_temperature 90.0(1)
_cell_measurement_theta_max 66.57
_cell_measurement_theta_min 3.37
_cell_volume 2191.10(15)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 90.0(1)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type 'Bruker APEX DUO'
_diffrn_measurement_method 'area detector'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0370
_diffrn_reflns_av_sigmaI/netI 0.0401
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 34168
_diffrn_reflns_theta_full 66.00
_diffrn_reflns_theta_max 67.40
_diffrn_reflns_theta_min 3.37
_exptl_absorpt_coefficient_mu 0.913
_exptl_absorpt_correction_T_max 0.848
_exptl_absorpt_correction_T_min 0.780
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.432
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description irregular
_exptl_crystal_F_000 1000
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.18
_refine_diff_density_max 0.190
_refine_diff_density_min -0.213
_refine_diff_density_rms 0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.06(12)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 1266
_refine_ls_number_reflns 13627
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.046
_refine_ls_R_factor_all 0.0420
_refine_ls_R_factor_gt 0.0402
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+1.8111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1047
_refine_ls_wR_factor_ref 0.1083
_reflns_number_gt 13323
_reflns_number_total 13627
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200031t_si_002.cif
_cod_data_source_block ra047
_cod_original_cell_volume 2191.10(14)
_cod_database_code 1501997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9404(3) 0.6835(3) 0.6505(3) 0.0194(7) Uani 1 1 d . A 1
C2 C 1.0146(3) 0.7250(3) 0.6648(3) 0.0198(7) Uani 1 1 d . A 1
H2 H 1.0014 0.7277 0.7309 0.024 Uiso 1 1 calc R A 1
C3 C 1.1002(3) 0.7591(3) 0.5885(3) 0.0193(7) Uani 1 1 d . A 1
C4 C 1.1080(3) 0.7686(3) 0.4831(3) 0.0199(7) Uani 1 1 d . A 1
C5 C 1.1910(3) 0.8204(3) 0.3937(3) 0.0214(7) Uani 1 1 d . A 1
H5 H 1.1701 0.8580 0.3283 0.026 Uiso 1 1 calc R A 1
C6 C 1.2626(3) 0.8683(3) 0.4072(3) 0.0211(7) Uani 1 1 d . A 1
H6A H 1.2681 0.9393 0.3514 0.025 Uiso 1 1 calc R A 1
H6B H 1.3405 0.8138 0.4018 0.025 Uiso 1 1 calc R A 1
C7 C 1.2145(3) 0.8938(3) 0.5107(3) 0.0182(7) Uani 1 1 d . A 1
C8 C 1.3018(3) 0.9178(3) 0.5339(3) 0.0186(7) Uani 1 1 d . A 1
C9 C 1.3929(3) 0.8059(3) 0.5698(3) 0.0183(7) Uani 1 1 d . A 1
C10 C 1.3441(3) 0.7654(3) 0.6898(3) 0.0202(7) Uani 1 1 d . A 1
C11 C 1.2267(3) 0.8567(3) 0.7159(3) 0.0207(7) Uani 1 1 d . A 1
C12 C 1.1389(3) 0.8238(3) 0.7027(3) 0.0209(7) Uani 1 1 d . A 1
H12A H 1.0681 0.8889 0.7009 0.025 Uiso 1 1 calc R A 1
H12B H 1.1199 0.7596 0.7619 0.025 Uiso 1 1 calc R A 1
C13 C 1.1858(3) 0.7897(3) 0.6033(3) 0.0189(7) Uani 1 1 d . A 1
C14 C 1.3018(3) 0.6836(3) 0.6147(3) 0.0188(7) Uani 1 1 d . A 1
C15 C 1.3078(3) 0.5720(3) 0.6126(3) 0.0229(8) Uani 1 1 d . A 1
H15A H 1.3080 0.5795 0.5448 0.034 Uiso 1 1 calc R A 1
H15B H 1.2415 0.5499 0.6640 0.034 Uiso 1 1 calc R A 1
H15C H 1.3776 0.5139 0.6275 0.034 Uiso 1 1 calc R A 1
C16 C 1.0003(3) 0.7749(3) 0.4690(3) 0.0205(7) Uani 1 1 d . A 1
C17 C 0.9117(3) 0.8910(3) 0.4654(3) 0.0234(8) Uani 1 1 d . A 1
H17A H 0.8407 0.8891 0.4649 0.035 Uiso 1 1 calc R A 1
H17B H 0.9395 0.9473 0.4034 0.035 Uiso 1 1 calc R A 1
H17C H 0.8978 0.9118 0.5255 0.035 Uiso 1 1 calc R A 1
C18 C 1.0242(3) 0.7379(3) 0.3777(3) 0.0249(8) Uani 1 1 d . A 1
H18A H 1.0779 0.6608 0.3847 0.037 Uiso 1 1 calc R A 1
H18B H 1.0571 0.7900 0.3149 0.037 Uiso 1 1 calc R A 1
H18C H 0.9529 0.7391 0.3748 0.037 Uiso 1 1 calc R A 1
C19 C 1.1065(3) 0.9976(3) 0.5027(3) 0.0216(7) Uani 1 1 d . A 1
H19A H 1.0653 1.0112 0.5696 0.032 Uiso 1 1 calc R A 1
H19B H 1.0573 0.9829 0.4802 0.032 Uiso 1 1 calc R A 1
H19C H 1.1284 1.0646 0.4532 0.032 Uiso 1 1 calc R A 1
C20 C 1.3699(3) 0.9886(3) 0.4420(3) 0.0219(8) Uani 1 1 d . A 1
C21 C 1.2470(3) 0.9605(3) 0.6276(3) 0.0209(8) Uani 1 1 d . A 1
C22 C 1.2702(3) 1.0517(3) 0.6354(3) 0.0273(8) Uani 1 1 d . A 1
H22A H 1.2727 1.0453 0.7025 0.033 Uiso 1 1 calc R A 1
H22B H 1.3229 1.0891 0.5755 0.033 Uiso 1 1 calc R A 1
C23 C 1.5068(3) 0.8318(3) 0.5154(3) 0.0203(7) Uani 1 1 d . A 1
H23 H 1.5643 0.7676 0.4874 0.024 Uiso 1 1 calc R A 1
C24 C 1.5599(3) 0.8576(3) 0.5702(3) 0.0245(8) Uani 1 1 d . A 1
H24A H 1.6239 0.8852 0.5211 0.037 Uiso 1 1 calc R A 1
H24B H 1.5873 0.7884 0.6220 0.037 Uiso 1 1 calc R A 1
H24C H 1.5029 0.9159 0.6033 0.037 Uiso 1 1 calc R A 1
C25 C 1.1895(3) 0.8699(3) 0.8208(3) 0.0255(8) Uani 1 1 d . A 1
H25A H 1.2508 0.8806 0.8306 0.038 Uiso 1 1 calc R A 1
H25B H 1.1722 0.8016 0.8725 0.038 Uiso 1 1 calc R A 1
H25C H 1.1213 0.9361 0.8273 0.038 Uiso 1 1 calc R A 1
O1 O 0.8755(2) 0.6352(2) 0.72108(19) 0.0286(6) Uani 1 1 d . A 1
O2 O 0.9493(2) 0.6918(2) 0.55597(18) 0.0226(5) Uani 1 1 d . A 1
O3 O 1.2146(2) 0.6990(2) 0.43195(19) 0.0231(5) Uani 1 1 d . A 1
O4 O 1.4206(2) 0.7420(2) 0.73865(19) 0.0214(5) Uani 1 1 d . A 1
O5 O 1.3219(2) 0.6643(2) 0.70738(18) 0.0209(5) Uani 1 1 d . A 1
O6 O 1.3972(2) 0.7175(2) 0.53979(17) 0.0193(5) Uani 1 1 d . A 1
O7 O 1.3356(2) 1.0794(2) 0.3849(2) 0.0288(6) Uani 1 1 d . A 1
O8 O 1.4830(2) 0.9335(2) 0.42869(19) 0.0239(6) Uani 1 1 d . A 1
O9 O 1.1613(2) 1.0683(2) 0.6260(2) 0.0260(6) Uani 1 1 d . A 1
H4O H 1.388(5) 0.711(5) 0.805(5) 0.049(15) Uiso 1 1 d . B 1
C1B C 0.8730(3) 1.0488(3) -0.0192(3) 0.0209(7) Uani 1 1 d . C 2
C2B C 0.8153(3) 0.9847(3) -0.0269(3) 0.0215(8) Uani 1 1 d . C 2
H2B H 0.8087 0.9973 -0.0915 0.026 Uiso 1 1 calc R C 2
C3B C 0.7716(3) 0.9087(3) 0.0545(3) 0.0186(7) Uani 1 1 d . C 2
C4B C 0.7667(3) 0.9058(3) 0.1565(3) 0.0212(7) Uani 1 1 d . C 2
C5B C 0.7176(3) 0.8253(3) 0.2495(3) 0.0223(8) Uani 1 1 d . C 2
H5B H 0.6825 0.8493 0.3131 0.027 Uiso 1 1 calc R C 2
C6B C 0.6671(3) 0.7499(3) 0.2442(3) 0.0232(8) Uani 1 1 d . C 2
H6B1 H 0.5999 0.7418 0.3042 0.028 Uiso 1 1 calc R C 2
H6B2 H 0.7238 0.6735 0.2465 0.028 Uiso 1 1 calc R C 2
C7B C 0.6308(3) 0.7986(3) 0.1455(3) 0.0213(8) Uani 1 1 d . C 2
C8B C 0.5993(3) 0.7107(3) 0.1297(3) 0.0206(7) Uani 1 1 d . C 2
C9B C 0.7088(3) 0.6210(3) 0.0879(3) 0.0204(7) Uani 1 1 d . C 2
C10B C 0.7401(3) 0.6705(3) -0.0323(3) 0.0201(7) Uani 1 1 d . C 2
C11B C 0.6460(3) 0.7872(3) -0.0534(3) 0.0231(8) Uani 1 1 d . C 2
C12B C 0.6859(3) 0.8734(3) -0.0468(3) 0.0224(8) Uani 1 1 d . C 2
H12C H 0.6215 0.9442 -0.0422 0.027 Uiso 1 1 calc R C 2
H12D H 0.7471 0.8921 -0.1097 0.027 Uiso 1 1 calc R C 2
C13B C 0.7305(3) 0.8258(3) 0.0469(3) 0.0203(7) Uani 1 1 d . C 2
C14B C 0.8356(3) 0.7104(3) 0.0320(3) 0.0198(7) Uani 1 1 d . C 2
C15B C 0.9508(3) 0.7048(3) 0.0257(3) 0.0226(8) Uani 1 1 d . C 2
H15D H 1.0060 0.6318 0.0164 0.034 Uiso 1 1 calc R C 2
H15E H 0.9476 0.7124 0.0888 0.034 Uiso 1 1 calc R C 2
H15F H 0.9742 0.7666 -0.0323 0.034 Uiso 1 1 calc R C 2
C16B C 0.7668(3) 1.0145(3) 0.1616(3) 0.0222(8) Uani 1 1 d . C 2
C17B C 0.6535(3) 1.1073(3) 0.1573(3) 0.0260(8) Uani 1 1 d . C 2
H17D H 0.6599 1.1793 0.1501 0.039 Uiso 1 1 calc R C 2
H17E H 0.5943 1.0873 0.2202 0.039 Uiso 1 1 calc R C 2
H17F H 0.6333 1.1152 0.0987 0.039 Uiso 1 1 calc R C 2
C18B C 0.8024(3) 0.9975(3) 0.2510(3) 0.0267(8) Uani 1 1 d . C 2
H18D H 0.8778 0.9405 0.2485 0.040 Uiso 1 1 calc R C 2
H18E H 0.7471 0.9714 0.3149 0.040 Uiso 1 1 calc R C 2
H18F H 0.8055 1.0695 0.2476 0.040 Uiso 1 1 calc R C 2
C19B C 0.5279(3) 0.9052(3) 0.1569(3) 0.0249(8) Uani 1 1 d . C 2
H19D H 0.5101 0.9470 0.0916 0.037 Uiso 1 1 calc R C 2
H19E H 0.5458 0.9537 0.1772 0.037 Uiso 1 1 calc R C 2
H19F H 0.4621 0.8829 0.2090 0.037 Uiso 1 1 calc R C 2
C20B C 0.5343(3) 0.6424(3) 0.2262(3) 0.0265(8) Uani 1 1 d . C 2
C21B C 0.5468(3) 0.7655(3) 0.0414(3) 0.0255(8) Uani 1 1 d . C 2
C22B C 0.4503(3) 0.7418(4) 0.0424(4) 0.0331(9) Uani 1 1 d . C 2
H22C H 0.4500 0.7393 -0.0222 0.040 Uiso 1 1 calc R C 2
H22D H 0.4159 0.6892 0.1050 0.040 Uiso 1 1 calc R C 2
C23B C 0.6821(3) 0.5081(3) 0.1466(3) 0.0222(8) Uani 1 1 d . C 2
H23B H 0.7495 0.4497 0.1698 0.027 Uiso 1 1 calc R C 2
C24B C 0.6459(3) 0.4585(3) 0.0962(3) 0.0268(8) Uani 1 1 d . C 2
H24D H 0.6193 0.3946 0.1470 0.040 Uiso 1 1 calc R C 2
H24E H 0.7109 0.4319 0.0415 0.040 Uiso 1 1 calc R C 2
H24F H 0.5842 0.5169 0.0677 0.040 Uiso 1 1 calc R C 2
C25B C 0.6211(4) 0.8258(3) -0.1549(3) 0.0310(9) Uani 1 1 d . C 2
H25D H 0.5976 0.7689 -0.1577 0.047 Uiso 1 1 calc R C 2
H25E H 0.6900 0.8349 -0.2111 0.047 Uiso 1 1 calc R C 2
H25F H 0.5600 0.8986 -0.1611 0.047 Uiso 1 1 calc R C 2
O1B O 0.9404(2) 1.0925(2) -0.09194(19) 0.0256(6) Uani 1 1 d . C 2
O2B O 0.8562(2) 1.0546(2) 0.07290(18) 0.0230(5) Uani 1 1 d . C 2
O3B O 0.8399(2) 0.8007(2) 0.20837(18) 0.0221(5) Uani 1 1 d . C 2
O4B O 0.7561(2) 0.5964(2) -0.0798(2) 0.0229(5) Uani 1 1 d . C 2
O5B O 0.8443(2) 0.6920(2) -0.05765(17) 0.0195(5) Uani 1 1 d . C 2
O6B O 0.8035(2) 0.6156(2) 0.10987(18) 0.0191(5) Uani 1 1 d . C 2
O7B O 0.4487(2) 0.6756(3) 0.2888(2) 0.0387(7) Uani 1 1 d . C 2
O8B O 0.5868(2) 0.5300(2) 0.23678(19) 0.0267(6) Uani 1 1 d . C 2
O9B O 0.4381(2) 0.8508(2) 0.0485(2) 0.0337(7) Uani 1 1 d . C 2
H4OB H 0.796(4) 0.617(4) -0.142(4) 0.033(13) Uiso 1 1 d . D 2
C1C C 0.3421(3) 0.5645(3) 0.0035(3) 0.0219(8) Uani 1 1 d . E 3
C2C C 0.2895(3) 0.5034(3) -0.0147(3) 0.0200(7) Uani 1 1 d . E 3
H2C H 0.2771 0.5277 -0.0793 0.024 Uiso 1 1 calc R E 3
C3C C 0.2586(3) 0.4143(3) 0.0569(3) 0.0180(7) Uani 1 1 d . E 3
C4C C 0.2670(3) 0.3884(3) 0.1611(3) 0.0193(7) Uani 1 1 d . E 3
C5C C 0.2341(3) 0.2911(3) 0.2439(3) 0.0221(8) Uani 1 1 d . E 3
H5C H 0.2068 0.2974 0.3146 0.027 Uiso 1 1 calc R E 3
C6C C 0.1849(3) 0.2218(3) 0.2277(3) 0.0208(7) Uani 1 1 d . E 3
H6C1 H 0.1252 0.1996 0.2905 0.025 Uiso 1 1 calc R E 3
H6C2 H 0.2456 0.1516 0.2143 0.025 Uiso 1 1 calc R E 3
C7C C 0.1328(3) 0.2895(3) 0.1366(3) 0.0196(7) Uani 1 1 d . E 3
C8C C 0.1002(3) 0.2129(3) 0.1078(3) 0.0191(7) Uani 1 1 d . E 3
C9C C 0.2071(3) 0.1420(3) 0.0440(3) 0.0199(7) Uani 1 1 d . E 3
C10C C 0.2179(3) 0.2196(3) -0.0725(3) 0.0212(7) Uani 1 1 d . E 3
C11C C 0.1157(3) 0.3290(3) -0.0659(3) 0.0206(7) Uani 1 1 d . E 3
C12C C 0.1571(3) 0.4065(3) -0.0476(3) 0.0207(7) Uani 1 1 d . E 3
H12E H 0.0911 0.4703 -0.0270 0.025 Uiso 1 1 calc R E 3
H12F H 0.2098 0.4386 -0.1118 0.025 Uiso 1 1 calc R E 3
C13C C 0.2189(3) 0.3390(3) 0.0368(3) 0.0189(7) Uani 1 1 d . E 3
C14C C 0.3265(3) 0.2376(3) -0.0043(3) 0.0198(7) Uani 1 1 d . E 3
C15C C 0.4438(3) 0.2331(3) -0.0177(3) 0.0243(8) Uani 1 1 d . E 3
H15G H 0.4504 0.2233 0.0481 0.036 Uiso 1 1 calc R E 3
H15H H 0.4579 0.3039 -0.0664 0.036 Uiso 1 1 calc R E 3
H15I H 0.4998 0.1691 -0.0437 0.036 Uiso 1 1 calc R E 3
C16C C 0.2627(3) 0.4876(3) 0.1845(3) 0.0218(8) Uani 1 1 d . E 3
C17C C 0.1439(3) 0.5754(3) 0.1967(3) 0.0261(8) Uani 1 1 d . E 3
H17G H 0.1464 0.6427 0.2033 0.039 Uiso 1 1 calc R E 3
H17H H 0.0901 0.5427 0.2579 0.039 Uiso 1 1 calc R E 3
H17I H 0.1192 0.5970 0.1366 0.039 Uiso 1 1 calc R E 3
C18C C 0.3063(4) 0.4535(3) 0.2743(3) 0.0287(9) Uani 1 1 d . E 3
H18G H 0.3818 0.3966 0.2645 0.043 Uiso 1 1 calc R E 3
H18H H 0.2537 0.4214 0.3373 0.043 Uiso 1 1 calc R E 3
H18I H 0.3115 0.5204 0.2793 0.043 Uiso 1 1 calc R E 3
C19C C 0.0259(3) 0.3833(3) 0.1724(3) 0.0205(7) Uani 1 1 d . E 3
H19G H -0.0048 0.4356 0.1149 0.031 Uiso 1 1 calc R E 3
H19H H 0.0459 0.4250 0.1985 0.031 Uiso 1 1 calc R E 3
H19I H -0.0315 0.3491 0.2267 0.031 Uiso 1 1 calc R E 3
C20C C 0.0471(3) 0.1274(3) 0.1959(3) 0.0217(8) Uani 1 1 d . E 3
C21C C 0.0315(3) 0.2846(3) 0.0300(3) 0.0202(7) Uani 1 1 d . E 3
C22C C -0.0639(3) 0.2588(3) 0.0314(3) 0.0251(8) Uani 1 1 d . E 3
H22E H -0.0739 0.2730 -0.0349 0.030 Uiso 1 1 calc R E 3
H22F H -0.0855 0.1931 0.0863 0.030 Uiso 1 1 calc R E 3
C23C C 0.1939(3) 0.0225(3) 0.0863(3) 0.0228(8) Uani 1 1 d . E 3
H23C H 0.2650 -0.0338 0.1043 0.027 Uiso 1 1 calc R E 3
C24C C 0.1673(4) -0.0191(3) 0.0228(3) 0.0295(9) Uani 1 1 d . E 3
H24G H 0.2339 -0.0336 -0.0355 0.044 Uiso 1 1 calc R E 3
H24H H 0.1026 0.0387 -0.0019 0.044 Uiso 1 1 calc R E 3
H24I H 0.1480 -0.0894 0.0646 0.044 Uiso 1 1 calc R E 3
C25C C 0.0731(3) 0.3914(3) -0.1607(3) 0.0277(8) Uani 1 1 d . E 3
H25G H 0.0538 0.3394 -0.1756 0.042 Uiso 1 1 calc R E 3
H25H H 0.1329 0.4182 -0.2190 0.042 Uiso 1 1 calc R E 3
H25I H 0.0053 0.4563 -0.1483 0.042 Uiso 1 1 calc R E 3
O1C O 0.3911(3) 0.6300(2) -0.0655(2) 0.0320(6) Uani 1 1 d . E 3
O2C O 0.3422(2) 0.5443(2) 0.09794(18) 0.0228(5) Uani 1 1 d . E 3
O3C O 0.3525(2) 0.2805(2) 0.19172(18) 0.0228(5) Uani 1 1 d . E 3
O4C O 0.2244(2) 0.1759(2) -0.1424(2) 0.0258(6) Uani 1 1 d . E 3
O5C O 0.3214(2) 0.2441(2) -0.09945(18) 0.0216(5) Uani 1 1 d . E 3
O6C O 0.3082(2) 0.1323(2) 0.05948(18) 0.0215(5) Uani 1 1 d . E 3
O7C O -0.0311(2) 0.1428(2) 0.2704(2) 0.0294(6) Uani 1 1 d . E 3
O8C O 0.0996(2) 0.0241(2) 0.18145(19) 0.0255(6) Uani 1 1 d . E 3
O9C O -0.0825(2) 0.3557(2) 0.0598(2) 0.0239(5) Uani 1 1 d . E 3
H4OC H 0.290(5) 0.130(4) -0.159(4) 0.035(13) Uiso 1 1 d . F 3
C1D C 0.4712(3) 0.1389(3) 0.6680(3) 0.0205(7) Uani 1 1 d . G 4
C2D C 0.5255(3) 0.2044(3) 0.6781(3) 0.0204(7) Uani 1 1 d . G 4
H2D H 0.5024 0.2194 0.7413 0.025 Uiso 1 1 calc R G 4
C3D C 0.6068(3) 0.2437(3) 0.6007(3) 0.0189(7) Uani 1 1 d . G 4
C4D C 0.6265(3) 0.2319(3) 0.4992(3) 0.0198(7) Uani 1 1 d . G 4
C5D C 0.7204(3) 0.2650(3) 0.4113(3) 0.0221(8) Uani 1 1 d . G 4
H5D H 0.7098 0.2894 0.3424 0.026 Uiso 1 1 calc R G 4
C6D C 0.7925(3) 0.3177(3) 0.4198(3) 0.0221(8) Uani 1 1 d . G 4
H6D1 H 0.8121 0.3761 0.3547 0.026 Uiso 1 1 calc R G 4
H6D2 H 0.8644 0.2586 0.4314 0.026 Uiso 1 1 calc R G 4
C7D C 0.7301(3) 0.3729(3) 0.5081(3) 0.0183(7) Uani 1 1 d . G 4
C8D C 0.8106(3) 0.4080(3) 0.5295(3) 0.0201(7) Uani 1 1 d . G 4
C9D C 0.8852(3) 0.3055(3) 0.5931(3) 0.0200(7) Uani 1 1 d . G 4
C10D C 0.8124(3) 0.2983(3) 0.7099(3) 0.0219(8) Uani 1 1 d . G 4
C11D C 0.7009(3) 0.3993(3) 0.7039(3) 0.0219(8) Uani 1 1 d . G 4
C12D C 0.6196(3) 0.3550(3) 0.6932(3) 0.0192(7) Uani 1 1 d . G 4
H12G H 0.5547 0.4199 0.6728 0.023 Uiso 1 1 calc R G 4
H12H H 0.5889 0.3044 0.7599 0.023 Uiso 1 1 calc R G 4
C13D C 0.6836(3) 0.2890(3) 0.6120(3) 0.0192(7) Uani 1 1 d . G 4
C14D C 0.7878(3) 0.1854(3) 0.6532(3) 0.0216(8) Uani 1 1 d . G 4
C15D C 0.7922(3) 0.0666(3) 0.6734(3) 0.0234(8) Uani 1 1 d . G 4
H15J H 0.8588 0.0129 0.6970 0.035 Uiso 1 1 calc R G 4
H15K H 0.7979 0.0567 0.6104 0.035 Uiso 1 1 calc R G 4
H15L H 0.7229 0.0525 0.7259 0.035 Uiso 1 1 calc R G 4
C16D C 0.5227(3) 0.2319(3) 0.4855(3) 0.0227(8) Uani 1 1 d . G 4
C17D C 0.4291(3) 0.3458(3) 0.4795(3) 0.0233(8) Uani 1 1 d . G 4
H17J H 0.3619 0.3394 0.4755 0.035 Uiso 1 1 calc R G 4
H17K H 0.4563 0.4033 0.4187 0.035 Uiso 1 1 calc R G 4
H17L H 0.4088 0.3679 0.5405 0.035 Uiso 1 1 calc R G 4
C18D C 0.5491(4) 0.1904(3) 0.3966(3) 0.0273(8) Uani 1 1 d . G 4
H18J H 0.6116 0.1186 0.4004 0.041 Uiso 1 1 calc R G 4
H18K H 0.5715 0.2471 0.3323 0.041 Uiso 1 1 calc R G 4
H18L H 0.4813 0.1787 0.3996 0.041 Uiso 1 1 calc R G 4
C19D C 0.6325(3) 0.4771(3) 0.4723(3) 0.0205(7) Uani 1 1 d . G 4
H19J H 0.6647 0.5337 0.4144 0.031 Uiso 1 1 calc R G 4
H19K H 0.5821 0.5103 0.5284 0.031 Uiso 1 1 calc R G 4
H19L H 0.5889 0.4532 0.4514 0.031 Uiso 1 1 calc R G 4
C20D C 0.8948(3) 0.4581(3) 0.4350(3) 0.0220(8) Uani 1 1 d . G 4
C21D C 0.7432(3) 0.4818(3) 0.6029(3) 0.0202(7) Uani 1 1 d . G 4
C22D C 0.7722(3) 0.5777(3) 0.5922(3) 0.0260(8) Uani 1 1 d . G 4
H22G H 0.8371 0.5969 0.5339 0.031 Uiso 1 1 calc R G 4
H22H H 0.7620 0.5921 0.6552 0.031 Uiso 1 1 calc R G 4
C23D C 1.0043(3) 0.3202(3) 0.5462(3) 0.0257(8) Uani 1 1 d . G 4
H23D H 1.0613 0.2468 0.5344 0.031 Uiso 1 1 calc R G 4
C24D C 1.0462(3) 0.3593(4) 0.6008(3) 0.0328(9) Uani 1 1 d . G 4
H24J H 1.1181 0.3748 0.5566 0.049 Uiso 1 1 calc R G 4
H24K H 1.0585 0.2998 0.6639 0.049 Uiso 1 1 calc R G 4
H24L H 0.9892 0.4286 0.6173 0.049 Uiso 1 1 calc R G 4
C25D C 0.6435(3) 0.4477(3) 0.7945(3) 0.0279(8) Uani 1 1 d . G 4
H25J H 0.6989 0.4661 0.8057 0.042 Uiso 1 1 calc R G 4
H25K H 0.6147 0.3914 0.8557 0.042 Uiso 1 1 calc R G 4
H25L H 0.5800 0.5166 0.7803 0.042 Uiso 1 1 calc R G 4
O1D O 0.4257(2) 0.0732(2) 0.74110(18) 0.0223(5) Uani 1 1 d . G 4
O2D O 0.4767(2) 0.1459(2) 0.57458(18) 0.0217(5) Uani 1 1 d . G 4
O3D O 0.7335(2) 0.1475(2) 0.46760(18) 0.0236(6) Uani 1 1 d . G 4
O4D O 0.8623(2) 0.2955(2) 0.7737(2) 0.0266(6) Uani 1 1 d . G 4
O5D O 0.7869(2) 0.1953(2) 0.74387(18) 0.0221(5) Uani 1 1 d . G 4
O6D O 0.8928(2) 0.2025(2) 0.58451(18) 0.0202(5) Uani 1 1 d . G 4
O7D O 0.8767(2) 0.5327(2) 0.3598(2) 0.0280(6) Uani 1 1 d . G 4
O8D O 1.0012(2) 0.4049(2) 0.4464(2) 0.0273(6) Uani 1 1 d . G 4
O9D O 0.6706(2) 0.5934(2) 0.57014(19) 0.0234(5) Uani 1 1 d . G 4
H4OD H 0.887(5) 0.237(5) 0.803(5) 0.06(2) Uiso 1 1 d . H 4
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0178(17) 0.0196(18) 0.0163(17) -0.0053(14) -0.0035(14) -0.0032(15)
C2 0.0183(18) 0.0209(19) 0.0196(18) -0.0069(14) -0.0033(14) -0.0065(16)
C3 0.0168(17) 0.0138(17) 0.0188(18) -0.0042(13) -0.0025(14) -0.0002(15)
C4 0.0155(17) 0.0165(18) 0.0200(17) -0.0059(14) -0.0024(14) -0.0003(15)
C5 0.0210(18) 0.0187(18) 0.0185(17) -0.0055(14) -0.0012(14) -0.0052(15)
C6 0.0175(17) 0.0213(18) 0.0162(17) -0.0020(14) -0.0016(14) -0.0052(15)
C7 0.0128(16) 0.0145(18) 0.0189(17) -0.0029(14) -0.0009(13) -0.0023(15)
C8 0.0132(17) 0.0129(17) 0.0244(18) -0.0042(14) -0.0050(14) -0.0009(15)
C9 0.0149(17) 0.0144(17) 0.0209(18) -0.0029(14) -0.0046(14) -0.0033(15)
C10 0.0170(17) 0.0187(18) 0.0211(18) -0.0046(14) -0.0027(14) -0.0058(15)
C11 0.0159(18) 0.0217(19) 0.0192(17) -0.0062(14) -0.0019(14) -0.0040(15)
C12 0.0165(17) 0.0197(19) 0.0207(18) -0.0079(14) -0.0003(14) -0.0034(15)
C13 0.0136(17) 0.0165(18) 0.0207(18) -0.0060(14) -0.0003(13) -0.0035(15)
C14 0.0176(17) 0.0146(17) 0.0171(17) -0.0019(13) -0.0021(14) -0.0042(15)
C15 0.0195(18) 0.0160(18) 0.0258(19) -0.0036(14) -0.0049(14) -0.0030(16)
C16 0.0193(18) 0.0218(19) 0.0177(17) -0.0052(14) -0.0006(14) -0.0092(16)
C17 0.0222(19) 0.023(2) 0.0238(18) -0.0058(15) -0.0054(15) -0.0076(16)
C18 0.027(2) 0.030(2) 0.0205(18) -0.0077(15) -0.0035(15) -0.0138(17)
C19 0.0176(17) 0.0193(18) 0.0236(18) -0.0027(14) -0.0076(14) -0.0036(15)
C20 0.0207(18) 0.021(2) 0.0238(18) -0.0031(15) -0.0081(15) -0.0077(16)
C21 0.0107(16) 0.0200(19) 0.0255(19) -0.0068(15) -0.0041(14) -0.0001(15)
C22 0.0220(19) 0.028(2) 0.036(2) -0.0139(17) -0.0085(16) -0.0071(17)
C23 0.0141(17) 0.0158(18) 0.0198(18) 0.0003(14) -0.0035(14) -0.0015(15)
C24 0.0218(19) 0.0215(19) 0.0270(19) -0.0053(15) -0.0048(15) -0.0077(16)
C25 0.0240(19) 0.026(2) 0.0257(19) -0.0103(15) -0.0042(15) -0.0077(17)
O1 0.0304(15) 0.0372(16) 0.0187(13) -0.0037(11) -0.0011(11) -0.0210(14)
O2 0.0240(13) 0.0253(14) 0.0177(12) -0.0053(10) -0.0029(10) -0.0110(11)
O3 0.0201(13) 0.0196(13) 0.0210(12) -0.0077(10) 0.0015(10) -0.0041(11)
O4 0.0175(12) 0.0218(13) 0.0200(13) -0.0020(10) -0.0055(10) -0.0056(11)
O5 0.0186(12) 0.0183(13) 0.0200(12) -0.0009(10) -0.0041(10) -0.0067(11)
O6 0.0161(12) 0.0158(12) 0.0179(12) -0.0035(9) -0.0001(10) -0.0039(10)
O7 0.0264(14) 0.0198(14) 0.0310(14) 0.0062(11) -0.0123(11) -0.0083(12)
O8 0.0178(13) 0.0190(13) 0.0243(13) 0.0016(10) -0.0043(10) -0.0057(11)
O9 0.0209(13) 0.0182(13) 0.0393(15) -0.0128(11) -0.0107(11) 0.0000(11)
C1B 0.0174(17) 0.0137(17) 0.0205(18) 0.0000(14) -0.0050(14) -0.0005(15)
C2B 0.0169(17) 0.0187(18) 0.0236(19) -0.0039(14) -0.0069(15) -0.0022(15)
C3B 0.0131(16) 0.0151(17) 0.0208(18) -0.0040(14) -0.0036(13) -0.0010(14)
C4B 0.0174(17) 0.0174(18) 0.0225(18) -0.0032(14) -0.0064(14) -0.0017(15)
C5B 0.0199(18) 0.0222(19) 0.0186(18) -0.0043(14) -0.0011(14) -0.0070(16)
C6B 0.0217(18) 0.0208(19) 0.0205(18) -0.0057(14) 0.0009(14) -0.0079(16)
C7B 0.0170(18) 0.0173(18) 0.0250(19) -0.0064(14) 0.0005(15) -0.0072(15)
C8B 0.0139(17) 0.0157(18) 0.0266(19) -0.0092(14) 0.0001(14) -0.0026(15)
C9B 0.0167(17) 0.0186(18) 0.0220(18) -0.0068(14) -0.0010(14) -0.0057(15)
C10B 0.0168(18) 0.0195(18) 0.0206(18) -0.0060(14) -0.0017(14) -0.0060(15)
C11B 0.027(2) 0.0165(18) 0.027(2) -0.0039(15) -0.0113(16) -0.0065(16)
C12B 0.0214(18) 0.0151(18) 0.0249(18) -0.0026(14) -0.0079(15) -0.0026(15)
C13B 0.0149(17) 0.0162(18) 0.0211(18) -0.0054(14) -0.0003(14) -0.0021(15)
C14B 0.0184(18) 0.0158(18) 0.0203(17) -0.0039(14) -0.0026(14) -0.0053(15)
C15B 0.0157(18) 0.0184(18) 0.0267(19) -0.0073(14) -0.0011(14) -0.0034(15)
C16B 0.0230(19) 0.0231(19) 0.0190(18) -0.0049(14) -0.0042(14) -0.0089(16)
C17B 0.028(2) 0.021(2) 0.031(2) -0.0102(15) -0.0101(16) -0.0052(17)
C18B 0.030(2) 0.027(2) 0.0250(19) -0.0091(16) -0.0075(16) -0.0102(17)
C19B 0.0174(18) 0.0221(19) 0.034(2) -0.0146(16) -0.0028(15) -0.0036(16)
C20B 0.026(2) 0.026(2) 0.030(2) -0.0139(16) -0.0004(17) -0.0116(18)
C21B 0.0171(19) 0.0159(19) 0.038(2) -0.0120(16) -0.0067(16) 0.0021(16)
C22B 0.025(2) 0.026(2) 0.054(3) -0.0211(19) -0.0127(19) -0.0023(18)
C23B 0.0188(18) 0.0177(19) 0.0183(17) -0.0023(14) 0.0027(14) -0.0059(15)
C24B 0.0227(19) 0.022(2) 0.029(2) -0.0065(15) -0.0010(16) -0.0080(16)
C25B 0.040(2) 0.021(2) 0.034(2) -0.0059(17) -0.0187(19) -0.0060(18)
O1B 0.0253(14) 0.0218(13) 0.0236(13) -0.0013(10) -0.0047(11) -0.0094(12)
O2B 0.0255(14) 0.0205(13) 0.0216(13) -0.0033(10) -0.0049(11) -0.0104(11)
O3B 0.0226(13) 0.0196(13) 0.0210(12) 0.0003(10) -0.0093(10) -0.0069(11)
O4B 0.0210(13) 0.0195(13) 0.0228(14) -0.0070(10) -0.0013(11) -0.0055(11)
O5B 0.0178(12) 0.0200(13) 0.0166(12) -0.0051(9) -0.0011(9) -0.0062(11)
O6B 0.0170(12) 0.0151(12) 0.0197(12) -0.0022(9) -0.0039(9) -0.0043(10)
O7B 0.0263(15) 0.0395(18) 0.0431(17) -0.0234(14) 0.0157(13) -0.0176(14)
O8B 0.0280(14) 0.0212(14) 0.0246(13) -0.0092(11) 0.0050(11) -0.0118(12)
O9B 0.0177(13) 0.0255(15) 0.063(2) -0.0239(14) -0.0164(13) 0.0034(12)
C1C 0.0233(19) 0.0174(18) 0.0161(17) -0.0002(14) -0.0046(14) -0.0042(16)
C2C 0.0192(18) 0.0215(19) 0.0144(17) -0.0042(14) -0.0044(14) -0.0035(15)
C3C 0.0111(16) 0.0189(18) 0.0174(17) -0.0054(14) -0.0011(13) -0.0017(14)
C4C 0.0142(16) 0.0178(18) 0.0171(17) -0.0031(14) -0.0019(13) -0.0019(15)
C5C 0.0203(18) 0.0216(19) 0.0186(18) -0.0049(14) -0.0026(14) -0.0052(16)
C6C 0.0213(18) 0.0153(17) 0.0179(17) -0.0020(13) -0.0016(14) -0.0055(15)
C7C 0.0158(17) 0.0154(18) 0.0200(18) -0.0042(14) -0.0022(14) -0.0020(15)
C8C 0.0134(16) 0.0162(18) 0.0205(18) -0.0060(14) -0.0023(14) -0.0002(15)
C9C 0.0156(17) 0.0185(18) 0.0238(18) -0.0089(14) -0.0025(14) -0.0040(15)
C10C 0.0157(17) 0.0245(19) 0.0248(18) -0.0103(15) -0.0012(14) -0.0089(16)
C11C 0.0185(18) 0.0197(19) 0.0208(17) -0.0044(14) -0.0046(14) -0.0059(16)
C12C 0.0181(17) 0.0196(18) 0.0189(17) -0.0043(14) -0.0028(14) -0.0048(15)
C13C 0.0130(17) 0.0180(18) 0.0171(17) -0.0035(14) -0.0013(14) -0.0018(15)
C14C 0.0159(17) 0.0185(18) 0.0197(17) -0.0035(14) -0.0014(14) -0.0064(15)
C15C 0.0150(18) 0.025(2) 0.0299(19) -0.0120(16) -0.0013(15) -0.0044(16)
C16C 0.0209(18) 0.0239(19) 0.0162(17) -0.0038(14) -0.0019(14) -0.0083(16)
C17C 0.028(2) 0.024(2) 0.0230(19) -0.0093(15) -0.0026(15) -0.0078(17)
C18C 0.036(2) 0.031(2) 0.0214(19) -0.0040(16) -0.0072(16) -0.0158(19)
C19C 0.0168(17) 0.0201(19) 0.0212(18) -0.0092(14) 0.0005(14) -0.0054(15)
C20C 0.0201(18) 0.0199(19) 0.0220(19) -0.0046(14) -0.0043(15) -0.0067(16)
C21C 0.0167(17) 0.0155(17) 0.0256(19) -0.0089(14) -0.0054(15) -0.0003(15)
C22C 0.0197(18) 0.022(2) 0.033(2) -0.0115(16) -0.0049(15) -0.0052(16)
C23C 0.0159(17) 0.0145(18) 0.0272(19) -0.0039(14) -0.0020(15) -0.0015(15)
C24C 0.028(2) 0.023(2) 0.037(2) -0.0090(17) -0.0070(17) -0.0094(17)
C25C 0.028(2) 0.028(2) 0.027(2) -0.0037(16) -0.0090(16) -0.0118(18)
O1C 0.0436(17) 0.0378(16) 0.0205(13) -0.0001(12) -0.0077(12) -0.0273(15)
O2C 0.0273(13) 0.0258(14) 0.0146(12) -0.0010(10) -0.0034(10) -0.0150(12)
O3C 0.0214(13) 0.0184(13) 0.0220(13) 0.0014(10) -0.0096(10) -0.0043(11)
O4C 0.0201(14) 0.0306(15) 0.0274(14) -0.0153(12) -0.0002(11) -0.0083(13)
O5C 0.0165(12) 0.0274(14) 0.0205(12) -0.0112(10) 0.0010(10) -0.0085(11)
O6C 0.0146(12) 0.0159(13) 0.0262(13) -0.0060(10) -0.0029(10) -0.0010(10)
O7C 0.0294(15) 0.0269(15) 0.0243(14) -0.0082(11) 0.0045(12) -0.0131(12)
O8C 0.0267(14) 0.0174(13) 0.0271(13) -0.0059(10) -0.0043(11) -0.0063(11)
O9C 0.0147(12) 0.0213(13) 0.0322(14) -0.0123(11) -0.0045(10) -0.0003(11)
C1D 0.0122(16) 0.0197(18) 0.0197(18) -0.0069(14) -0.0008(13) 0.0010(15)
C2D 0.0175(17) 0.0166(18) 0.0192(17) -0.0034(14) -0.0029(14) -0.0022(15)
C3D 0.0157(17) 0.0137(17) 0.0178(17) 0.0004(13) -0.0045(14) -0.0012(14)
C4D 0.0193(18) 0.0143(17) 0.0193(17) -0.0047(13) -0.0007(14) -0.0042(15)
C5D 0.0213(18) 0.0213(19) 0.0175(17) -0.0035(14) -0.0040(14) -0.0049(16)
C6D 0.0177(17) 0.0228(19) 0.0155(17) -0.0043(14) 0.0029(13) -0.0061(16)
C7D 0.0138(16) 0.0176(18) 0.0174(17) -0.0023(14) -0.0026(13) -0.0043(15)
C8D 0.0176(17) 0.0151(17) 0.0200(18) -0.0028(14) -0.0031(14) -0.0029(15)
C9D 0.0190(18) 0.0135(17) 0.0236(18) -0.0039(14) -0.0058(14) -0.0034(15)
C10D 0.0213(19) 0.0178(19) 0.0237(19) -0.0034(14) -0.0067(15) -0.0058(16)
C11D 0.0202(18) 0.0174(18) 0.0238(19) -0.0061(14) -0.0059(15) -0.0024(16)
C12D 0.0170(17) 0.0187(18) 0.0164(16) -0.0046(14) -0.0013(13) -0.0046(15)
C13D 0.0203(18) 0.0144(18) 0.0182(18) -0.0045(14) -0.0034(14) -0.0036(15)
C14D 0.0187(18) 0.0155(18) 0.0236(19) -0.0016(14) -0.0051(15) -0.0040(15)
C15D 0.0223(19) 0.0170(18) 0.0231(19) -0.0023(14) -0.0033(15) -0.0059(16)
C16D 0.0236(19) 0.0202(19) 0.0202(18) -0.0025(14) -0.0028(14) -0.0099(16)
C17D 0.0217(19) 0.024(2) 0.0225(18) -0.0054(15) -0.0068(15) -0.0067(16)
C18D 0.032(2) 0.030(2) 0.0192(18) -0.0065(15) -0.0008(15) -0.0155(18)
C19D 0.0190(17) 0.0148(18) 0.0219(18) -0.0018(14) -0.0043(14) -0.0049(15)
C20D 0.0185(18) 0.0194(19) 0.027(2) -0.0084(16) -0.0036(15) -0.0062(15)
C21D 0.0159(17) 0.0185(19) 0.0246(19) -0.0055(14) -0.0075(14) -0.0032(15)
C22D 0.0208(19) 0.0203(19) 0.035(2) -0.0060(16) -0.0099(16) -0.0050(16)
C23D 0.0150(18) 0.0208(19) 0.033(2) -0.0043(16) -0.0050(15) -0.0031(16)
C24D 0.022(2) 0.034(2) 0.039(2) -0.0067(18) -0.0074(17) -0.0115(18)
C25D 0.028(2) 0.027(2) 0.027(2) -0.0094(17) -0.0065(16) -0.0062(17)
O1D 0.0196(13) 0.0202(13) 0.0199(13) -0.0048(10) 0.0013(10) -0.0077(11)
O2D 0.0201(13) 0.0203(13) 0.0201(13) -0.0040(10) -0.0007(10) -0.0090(11)
O3D 0.0208(13) 0.0176(13) 0.0235(13) -0.0067(10) -0.0002(10) -0.0036(11)
O4D 0.0315(15) 0.0198(15) 0.0298(15) -0.0019(12) -0.0167(12) -0.0066(13)
O5D 0.0223(13) 0.0168(13) 0.0216(13) -0.0003(10) -0.0058(10) -0.0066(11)
O6D 0.0157(12) 0.0164(12) 0.0234(13) -0.0045(10) -0.0033(10) -0.0042(10)
O7D 0.0245(14) 0.0270(15) 0.0241(14) 0.0023(11) -0.0053(11) -0.0117(12)
O8D 0.0178(13) 0.0271(15) 0.0291(14) -0.0025(11) -0.0036(11) -0.0086(12)
O9D 0.0205(13) 0.0160(13) 0.0323(14) -0.0066(10) -0.0101(11) -0.0025(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 117.7(3)
O1 C1 C2 123.1(3)
O2 C1 C2 119.0(3)
C3 C2 C1 122.9(3)
C3 C2 H2 118.6
C1 C2 H2 118.5
C2 C3 C4 116.7(3)
C2 C3 C13 123.9(3)
C4 C3 C13 119.4(3)
O3 C4 C5 58.8(2)
O3 C4 C3 114.3(3)
C5 C4 C3 119.6(3)
O3 C4 C16 116.6(3)
C5 C4 C16 118.9(3)
C3 C4 C16 116.0(3)
O3 C5 C4 59.2(2)
O3 C5 C6 117.1(3)
C4 C5 C6 120.9(3)
O3 C5 H5 115.9
C4 C5 H5 115.9
C6 C5 H5 115.9
C5 C6 C7 112.9(3)
C5 C6 H6A 109.0
C7 C6 H6A 109.0
C5 C6 H6B 109.0
C7 C6 H6B 109.0
H6A C6 H6B 107.8
C6 C7 C19 105.4(3)
C6 C7 C8 112.2(3)
C19 C7 C8 111.6(3)
C6 C7 C13 112.3(3)
C19 C7 C13 111.2(3)
C8 C7 C13 104.4(3)
C20 C8 C21 114.4(3)
C20 C8 C9 104.2(3)
C21 C8 C9 101.2(3)
C20 C8 C7 114.0(3)
C21 C8 C7 111.2(3)
C9 C8 C7 110.6(3)
O6 C9 C23 109.3(3)
O6 C9 C8 110.9(3)
C23 C9 C8 105.4(3)
O6 C9 C10 102.6(3)
C23 C9 C10 123.1(3)
C8 C9 C10 105.3(3)
O4 C10 O5 110.6(3)
O4 C10 C11 117.2(3)
O5 C10 C11 107.3(3)
O4 C10 C9 112.4(3)
O5 C10 C9 102.9(3)
C11 C10 C9 105.2(3)
C25 C11 C21 115.2(3)
C25 C11 C12 111.0(3)
C21 C11 C12 107.6(3)
C25 C11 C10 114.7(3)
C21 C11 C10 100.9(3)
C12 C11 C10 106.7(3)
C11 C12 C13 111.3(3)
C11 C12 H12A 109.4
C13 C12 H12A 109.4
C11 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
C3 C13 C12 111.9(3)
C3 C13 C7 108.8(3)
C12 C13 C7 108.1(3)
C3 C13 C14 112.7(3)
C12 C13 C14 104.8(3)
C7 C13 C14 110.5(3)
O6 C14 O5 101.9(3)
O6 C14 C15 110.2(3)
O5 C14 C15 107.6(3)
O6 C14 C13 109.0(3)
O5 C14 C13 109.4(3)
C15 C14 C13 117.6(3)
O2 C16 C17 107.4(3)
O2 C16 C18 103.3(3)
C17 C16 C18 111.7(3)
O2 C16 C4 109.2(3)
C17 C16 C4 111.8(3)
C18 C16 C4 113.0(3)
O7 C20 O8 121.4(3)
O7 C20 C8 128.5(3)
O8 C20 C8 110.1(3)
O9 C21 C22 60.4(2)
O9 C21 C11 119.5(3)
C22 C21 C11 124.1(3)
O9 C21 C8 120.7(3)
C22 C21 C8 123.8(3)
C11 C21 C8 103.9(3)
O9 C22 C21 58.4(2)
O9 C22 H22A 117.9
C21 C22 H22A 117.9
O9 C22 H22B 117.9
C21 C22 H22B 117.9
H22A C22 H22B 115.1
O8 C23 C24 107.1(3)
O8 C23 C9 103.7(3)
C24 C23 C9 120.9(3)
O8 C23 H23 108.2
C24 C23 H23 108.2
C9 C23 H23 108.2
C1 O2 C16 119.2(3)
C5 O3 C4 62.0(2)
C10 O4 H4O 105(3)
C14 O5 C10 102.8(2)
C14 O6 C9 102.0(2)
C20 O8 C23 112.5(3)
C21 O9 C22 61.2(2)
O1B C1B O2B 118.1(3)
O1B C1B C2B 123.1(3)
O2B C1B C2B 118.7(3)
C3B C2B C1B 121.9(3)
C3B C2B H2B 119.1
C1B C2B H2B 119.1
C2B C3B C4B 116.9(3)
C2B C3B C13B 123.3(3)
C4B C3B C13B 119.8(3)
O3B C4B C5B 59.0(2)
O3B C4B C3B 114.1(3)
C5B C4B C3B 119.5(3)
O3B C4B C16B 115.7(3)
C5B C4B C16B 120.5(3)
C3B C4B C16B 115.2(3)
O3B C5B C4B 59.9(2)
O3B C5B C6B 116.9(3)
C4B C5B C6B 121.4(3)
O3B C5B H5B 115.7
C4B C5B H5B 115.7
C6B C5B H5B 115.7
C5B C6B C7B 111.4(3)
C5B C6B H6B1 109.3
C7B C6B H6B1 109.3
C5B C6B H6B2 109.3
C7B C6B H6B2 109.3
H6B1 C6B H6B2 108.0
C19B C7B C6B 106.3(3)
C19B C7B C8B 110.9(3)
C6B C7B C8B 111.6(3)
C19B C7B C13B 111.9(3)
C6B C7B C13B 112.2(3)
C8B C7B C13B 104.2(3)
C20B C8B C21B 114.9(3)
C20B C8B C9B 104.6(3)
C21B C8B C9B 100.6(3)
C20B C8B C7B 114.4(3)
C21B C8B C7B 110.9(3)
C9B C8B C7B 110.3(3)
O6B C9B C23B 109.2(3)
O6B C9B C8B 111.0(3)
C23B C9B C8B 104.3(3)
O6B C9B C10B 102.8(3)
C23B C9B C10B 123.4(3)
C8B C9B C10B 105.9(3)
O4B C10B O5B 110.5(3)
O4B C10B C11B 116.3(3)
O5B C10B C11B 108.0(3)
O4B C10B C9B 113.3(3)
O5B C10B C9B 102.7(3)
C11B C10B C9B 105.0(3)
C25B C11B C21B 115.1(3)
C25B C11B C12B 111.1(3)
C21B C11B C12B 108.2(3)
C25B C11B C10B 115.0(3)
C21B C11B C10B 100.7(3)
C12B C11B C10B 105.9(3)
C11B C12B C13B 111.4(3)
C11B C12B H12C 109.4
C13B C12B H12C 109.4
C11B C12B H12D 109.4
C13B C12B H12D 109.4
H12C C12B H12D 108.0
C3B C13B C12B 112.5(3)
C3B C13B C7B 109.3(3)
C12B C13B C7B 108.1(3)
C3B C13B C14B 110.3(3)
C12B C13B C14B 105.5(3)
C7B C13B C14B 111.1(3)
O5B C14B O6B 101.9(3)
O5B C14B C15B 108.3(3)
O6B C14B C15B 110.9(3)
O5B C14B C13B 108.4(3)
O6B C14B C13B 108.5(3)
C15B C14B C13B 117.7(3)
C14B C15B H15D 109.5
C14B C15B H15E 109.5
H15D C15B H15E 109.5
C14B C15B H15F 109.5
H15D C15B H15F 109.5
H15E C15B H15F 109.5
O2B C16B C18B 102.9(3)
O2B C16B C4B 108.6(3)
C18B C16B C4B 113.4(3)
O2B C16B C17B 107.9(3)
C18B C16B C17B 112.1(3)
C4B C16B C17B 111.4(3)
C16B C17B H17D 109.5
C16B C17B H17E 109.5
H17D C17B H17E 109.5
C16B C17B H17F 109.5
H17D C17B H17F 109.5
H17E C17B H17F 109.5
C16B C18B H18D 109.5
C16B C18B H18E 109.5
H18D C18B H18E 109.5
C16B C18B H18F 109.5
H18D C18B H18F 109.5
H18E C18B H18F 109.5
C7B C19B H19D 109.5
C7B C19B H19E 109.5
H19D C19B H19E 109.5
C7B C19B H19F 109.5
H19D C19B H19F 109.5
H19E C19B H19F 109.5
O7B C20B O8B 121.0(4)
O7B C20B C8B 128.7(4)
O8B C20B C8B 110.3(3)
O9B C21B C22B 60.5(2)
O9B C21B C8B 120.8(3)
C22B C21B C8B 123.8(4)
O9B C21B C11B 118.9(3)
C22B C21B C11B 124.0(4)
C8B C21B C11B 104.2(3)
O9B C22B C21B 58.3(2)
O9B C22B H22C 117.9
C21B C22B H22C 117.9
O9B C22B H22D 117.9
C21B C22B H22D 117.9
H22C C22B H22D 115.1
O8B C23B C24B 106.4(3)
O8B C23B C9B 104.8(3)
C24B C23B C9B 119.7(3)
O8B C23B H23B 108.5
C24B C23B H23B 108.5
C9B C23B H23B 108.5
C23B C24B H24D 109.5
C23B C24B H24E 109.5
H24D C24B H24E 109.5
C23B C24B H24F 109.5
H24D C24B H24F 109.5
H24E C24B H24F 109.5
C11B C25B H25D 109.5
C11B C25B H25E 109.5
H25D C25B H25E 109.5
C11B C25B H25F 109.5
H25D C25B H25F 109.5
H25E C25B H25F 109.5
C1B O2B C16B 120.5(3)
C5B O3B C4B 61.0(2)
C10B O4B H4OB 108(3)
C14B O5B C10B 103.2(2)
C9B O6B C14B 102.2(3)
C20B O8B C23B 112.2(3)
C21B O9B C22B 61.2(2)
O1C C1C O2C 117.9(3)
O1C C1C C2C 122.5(3)
O2C C1C C2C 119.6(3)
C3C C2C C1C 121.8(3)
C3C C2C H2C 119.1
C1C C2C H2C 119.1
C2C C3C C4C 116.8(3)
C2C C3C C13C 123.4(3)
C4C C3C C13C 119.8(3)
O3C C4C C5C 58.6(2)
O3C C4C C3C 113.5(3)
C5C C4C C3C 119.6(3)
O3C C4C C16C 116.4(3)
C5C C4C C16C 120.9(3)
C3C C4C C16C 115.0(3)
O3C C5C C4C 60.1(2)
O3C C5C C6C 116.9(3)
C4C C5C C6C 121.2(3)
O3C C5C H5C 115.7
C4C C5C H5C 115.7
C6C C5C H5C 115.7
C5C C6C C7C 111.4(3)
C5C C6C H6C1 109.3
C7C C6C H6C1 109.3
C5C C6C H6C2 109.3
C7C C6C H6C2 109.3
H6C1 C6C H6C2 108.0
C19C C7C C8C 110.2(3)
C19C C7C C6C 105.7(3)
C8C C7C C6C 111.8(3)
C19C C7C C13C 112.1(3)
C8C C7C C13C 105.0(3)
C6C C7C C13C 112.3(3)
C20C C8C C21C 113.1(3)
C20C C8C C9C 105.0(3)
C21C C8C C9C 100.4(3)
C20C C8C C7C 115.9(3)
C21C C8C C7C 110.9(3)
C9C C8C C7C 110.2(3)
O6C C9C C8C 111.2(3)
O6C C9C C23C 108.0(3)
C8C C9C C23C 104.9(3)
O6C C9C C10C 102.9(3)
C8C C9C C10C 105.0(3)
C23C C9C C10C 124.6(3)
O4C C10C O5C 109.9(3)
O4C C10C C11C 111.4(3)
O5C C10C C11C 109.3(3)
O4C C10C C9C 119.2(3)
O5C C10C C9C 101.6(3)
C11C C10C C9C 104.7(3)
C21C C11C C25C 115.2(3)
C21C C11C C10C 101.1(3)
C25C C11C C10C 114.9(3)
C21C C11C C12C 109.6(3)
C25C C11C C12C 110.0(3)
C10C C11C C12C 105.4(3)
C11C C12C C13C 110.8(3)
C11C C12C H12E 109.5
C13C C12C H12E 109.5
C11C C12C H12F 109.5
C13C C12C H12F 109.5
H12E C12C H12F 108.1
C3C C13C C12C 111.5(3)
C3C C13C C7C 109.5(3)
C12C C13C C7C 107.7(3)
C3C C13C C14C 111.0(3)
C12C C13C C14C 105.9(3)
C7C C13C C14C 111.0(3)
O6C C14C O5C 102.5(3)
O6C C14C C15C 110.1(3)
O5C C14C C15C 108.4(3)
O6C C14C C13C 108.6(3)
O5C C14C C13C 107.9(3)
C15C C14C C13C 118.2(3)
O2C C16C C4C 108.4(3)
O2C C16C C18C 103.6(3)
C4C C16C C18C 113.7(3)
O2C C16C C17C 107.3(3)
C4C C16C C17C 111.6(3)
C18C C16C C17C 111.6(3)
O7C C20C O8C 121.3(3)
O7C C20C C8C 128.4(3)
O8C C20C C8C 110.3(3)
O9C C21C C22C 59.8(2)
O9C C21C C11C 120.5(3)
C22C C21C C11C 123.9(3)
O9C C21C C8C 120.5(3)
C22C C21C C8C 123.2(3)
C11C C21C C8C 104.3(3)
O9C C22C C21C 58.6(2)
O9C C22C H22E 117.9
C21C C22C H22E 117.9
O9C C22C H22F 117.9
C21C C22C H22F 117.9
H22E C22C H22F 115.1
O8C C23C C24C 107.4(3)
O8C C23C C9C 105.0(3)
C24C C23C C9C 119.6(3)
O8C C23C H23C 108.1
C24C C23C H23C 108.1
C9C C23C H23C 108.1
C1C O2C C16C 118.8(3)
C5C O3C C4C 61.3(2)
C10C O4C H4OC 110(3)
C14C O5C C10C 103.6(2)
C14C O6C C9C 102.4(3)
C20C O8C C23C 113.1(3)
C21C O9C C22C 61.6(2)
O1D C1D O2D 118.1(3)
O1D C1D C2D 122.6(3)
O2D C1D C2D 119.2(3)
C3D C2D C1D 121.5(3)
C3D C2D H2D 119.2
C1D C2D H2D 119.2
C2D C3D C4D 116.1(3)
C2D C3D C13D 123.9(3)
C4D C3D C13D 119.8(3)
O3D C4D C5D 58.8(2)
O3D C4D C3D 113.2(3)
C5D C4D C3D 119.8(3)
O3D C4D C16D 117.1(3)
C5D C4D C16D 121.8(3)
C3D C4D C16D 114.0(3)
O3D C5D C4D 59.8(2)
O3D C5D C6D 116.5(3)
C4D C5D C6D 120.9(3)
O3D C5D H5D 115.9
C4D C5D H5D 115.9
C6D C5D H5D 115.9
C5D C6D C7D 111.8(3)
C5D C6D H6D1 109.2
C7D C6D H6D1 109.2
C5D C6D H6D2 109.2
C7D C6D H6D2 109.2
H6D1 C6D H6D2 107.9
C19D C7D C8D 111.6(3)
C19D C7D C6D 104.6(3)
C8D C7D C6D 112.0(3)
C19D C7D C13D 111.7(3)
C8D C7D C13D 104.7(3)
C6D C7D C13D 112.3(3)
C20D C8D C21D 113.2(3)
C20D C8D C9D 104.6(3)
C21D C8D C9D 100.5(3)
C20D C8D C7D 114.9(3)
C21D C8D C7D 111.1(3)
C9D C8D C7D 111.4(3)
O6D C9D C8D 110.7(3)
O6D C9D C23D 108.9(3)
C8D C9D C23D 105.5(3)
O6D C9D C10D 102.6(3)
C8D C9D C10D 105.3(3)
C23D C9D C10D 123.6(3)
O4D C10D O5D 109.7(3)
O4D C10D C11D 112.5(3)
O5D C10D C11D 108.7(3)
O4D C10D C9D 118.4(3)
O5D C10D C9D 102.1(3)
C11D C10D C9D 104.6(3)
C21D C11D C25D 114.3(3)
C21D C11D C10D 100.8(3)
C25D C11D C10D 115.2(3)
C21D C11D C12D 109.4(3)
C25D C11D C12D 110.4(3)
C10D C11D C12D 106.0(3)
C11D C12D C13D 110.7(3)
C11D C12D H12G 109.5
C13D C12D H12G 109.5
C11D C12D H12H 109.5
C13D C12D H12H 109.5
H12G C12D H12H 108.1
C3D C13D C12D 111.9(3)
C3D C13D C7D 110.3(3)
C12D C13D C7D 107.5(3)
C3D C13D C14D 110.9(3)
C12D C13D C14D 105.1(3)
C7D C13D C14D 111.0(3)
O6D C14D O5D 102.3(3)
O6D C14D C15D 109.6(3)
O5D C14D C15D 108.3(3)
O6D C14D C13D 108.9(3)
O5D C14D C13D 109.0(3)
C15D C14D C13D 117.7(3)
O2D C16D C4D 107.9(3)
O2D C16D C18D 102.9(3)
C4D C16D C18D 113.6(3)
O2D C16D C17D 108.0(3)
C4D C16D C17D 112.9(3)
C18D C16D C17D 110.8(3)
O7D C20D O8D 121.9(3)
O7D C20D C8D 128.6(3)
O8D C20D C8D 109.5(3)
O9D C21D C22D 61.0(2)
O9D C21D C11D 120.7(3)
C22D C21D C11D 124.9(3)
O9D C21D C8D 120.0(3)
C22D C21D C8D 122.8(3)
C11D C21D C8D 103.5(3)
C21D C22D O9D 58.4(2)
C21D C22D H22G 117.9
O9D C22D H22G 117.9
C21D C22D H22H 117.9
O9D C22D H22H 117.9
H22G C22D H22H 115.1
O8D C23D C24D 107.7(3)
O8D C23D C9D 104.4(3)
C24D C23D C9D 120.0(3)
O8D C23D H23D 108.1
C24D C23D H23D 108.1
C9D C23D H23D 108.1
C1D O2D C16D 119.0(3)
C5D O3D C4D 61.4(2)
C10D O4D H4OD 112(5)
C14D O5D C10D 103.4(3)
C9D O6D C14D 102.2(3)
C20D O8D C23D 113.4(3)
C21D O9D C22D 60.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.215(4)
C1 O2 1.337(4)
C1 C2 1.468(5)
C2 C3 1.342(5)
C2 H2 0.9500
C3 C4 1.499(5)
C3 C13 1.511(5)
C4 O3 1.447(4)
C4 C5 1.488(5)
C4 C16 1.526(5)
C5 O3 1.441(4)
C5 C6 1.495(5)
C5 H5 1.0000
C6 C7 1.545(5)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C19 1.545(5)
C7 C8 1.552(5)
C7 C13 1.577(4)
C8 C20 1.515(5)
C8 C21 1.525(5)
C8 C9 1.546(5)
C9 O6 1.427(4)
C9 C23 1.538(5)
C9 C10 1.581(5)
C10 O4 1.370(4)
C10 O5 1.430(4)
C10 C11 1.557(5)
C11 C25 1.509(5)
C11 C21 1.519(5)
C11 C12 1.548(5)
C12 C13 1.548(5)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.630(5)
C14 O6 1.425(4)
C14 O5 1.428(4)
C14 C15 1.503(5)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 O2 1.471(4)
C16 C17 1.516(5)
C16 C18 1.521(5)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 O7 1.198(4)
C20 O8 1.356(4)
C21 O9 1.427(4)
C21 C22 1.467(5)
C22 O9 1.455(4)
C22 H22A 0.9900
C22 H22B 0.9900
C23 O8 1.479(4)
C23 C24 1.509(5)
C23 H23 1.0000
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
O4 H4O 0.90(6)
C1B O1B 1.218(4)
C1B O2B 1.339(4)
C1B C2B 1.464(5)
C2B C3B 1.340(5)
C2B H2B 0.9500
C3B C4B 1.494(5)
C3B C13B 1.519(5)
C4B O3B 1.462(4)
C4B C5B 1.477(5)
C4B C16B 1.516(5)
C5B O3B 1.448(4)
C5B C6B 1.502(5)
C5B H5B 1.0000
C6B C7B 1.547(5)
C6B H6B1 0.9900
C6B H6B2 0.9900
C7B C19B 1.534(5)
C7B C8B 1.563(5)
C7B C13B 1.575(5)
C8B C20B 1.507(5)
C8B C21B 1.526(5)
C8B C9B 1.551(5)
C9B O6B 1.420(4)
C9B C23B 1.538(5)
C9B C10B 1.581(5)
C10B O4B 1.366(4)
C10B O5B 1.430(4)
C10B C11B 1.560(5)
C11B C25B 1.526(5)
C11B C21B 1.528(5)
C11B C12B 1.540(5)
C12B C13B 1.545(5)
C12B H12C 0.9900
C12B H12D 0.9900
C13B C14B 1.631(5)
C14B O5B 1.423(4)
C14B O6B 1.426(4)
C14B C15B 1.497(5)
C15B H15D 0.9800
C15B H15E 0.9800
C15B H15F 0.9800
C16B O2B 1.475(4)
C16B C18B 1.511(5)
C16B C17B 1.520(5)
C17B H17D 0.9800
C17B H17E 0.9800
C17B H17F 0.9800
C18B H18D 0.9800
C18B H18E 0.9800
C18B H18F 0.9800
C19B H19D 0.9800
C19B H19E 0.9800
C19B H19F 0.9800
C20B O7B 1.200(5)
C20B O8B 1.355(5)
C21B O9B 1.428(5)
C21B C22B 1.471(6)
C22B O9B 1.461(5)
C22B H22C 0.9900
C22B H22D 0.9900
C23B O8B 1.468(4)
C23B C24B 1.515(5)
C23B H23B 1.0000
C24B H24D 0.9800
C24B H24E 0.9800
C24B H24F 0.9800
C25B H25D 0.9800
C25B H25E 0.9800
C25B H25F 0.9800
O4B H4OB 0.86(5)
C1C O1C 1.218(4)
C1C O2C 1.332(4)
C1C C2C 1.465(5)
C2C C3C 1.336(5)
C2C H2C 0.9500
C3C C4C 1.499(5)
C3C C13C 1.520(5)
C4C O3C 1.461(4)
C4C C5C 1.477(5)
C4C C16C 1.507(5)
C5C O3C 1.438(4)
C5C C6C 1.507(5)
C5C H5C 1.0000
C6C C7C 1.555(5)
C6C H6C1 0.9900
C6C H6C2 0.9900
C7C C19C 1.537(5)
C7C C8C 1.553(5)
C7C C13C 1.567(5)
C8C C20C 1.509(5)
C8C C21C 1.537(5)
C8C C9C 1.541(5)
C9C O6C 1.428(4)
C9C C23C 1.544(5)
C9C C10C 1.609(5)
C10C O4C 1.369(4)
C10C O5C 1.438(4)
C10C C11C 1.546(5)
C11C C21C 1.503(5)
C11C C25C 1.531(5)
C11C C12C 1.547(5)
C12C C13C 1.553(5)
C12C H12E 0.9900
C12C H12F 0.9900
C13C C14C 1.629(5)
C14C O6C 1.416(4)
C14C O5C 1.427(4)
C14C C15C 1.496(5)
C15C H15G 0.9800
C15C H15H 0.9800
C15C H15I 0.9800
C16C O2C 1.475(4)
C16C C18C 1.516(5)
C16C C17C 1.531(5)
C17C H17G 0.9800
C17C H17H 0.9800
C17C H17I 0.9800
C18C H18G 0.9800
C18C H18H 0.9800
C18C H18I 0.9800
C19C H19G 0.9800
C19C H19H 0.9800
C19C H19I 0.9800
C20C O7C 1.202(5)
C20C O8C 1.344(5)
C21C O9C 1.426(4)
C21C C22C 1.470(5)
C22C O9C 1.445(4)
C22C H22E 0.9900
C22C H22F 0.9900
C23C O8C 1.473(4)
C23C C24C 1.511(5)
C23C H23C 1.0000
C24C H24G 0.9800
C24C H24H 0.9800
C24C H24I 0.9800
C25C H25G 0.9800
C25C H25H 0.9800
C25C H25I 0.9800
O4C H4OC 0.84(5)
C1D O1D 1.218(4)
C1D O2D 1.342(4)
C1D C2D 1.463(5)
C2D C3D 1.336(5)
C2D H2D 0.9500
C3D C4D 1.503(5)
C3D C13D 1.513(5)
C4D O3D 1.452(4)
C4D C5D 1.476(5)
C4D C16D 1.507(5)
C5D O3D 1.437(4)
C5D C6D 1.510(5)
C5D H5D 1.0000
C6D C7D 1.550(5)
C6D H6D1 0.9900
C6D H6D2 0.9900
C7D C19D 1.549(5)
C7D C8D 1.549(5)
C7D C13D 1.570(4)
C8D C20D 1.520(5)
C8D C21D 1.538(5)
C8D C9D 1.538(5)
C9D O6D 1.419(4)
C9D C23D 1.540(5)
C9D C10D 1.605(5)
C10D O4D 1.367(5)
C10D O5D 1.424(4)
C10D C11D 1.553(5)
C11D C21D 1.521(5)
C11D C25D 1.526(5)
C11D C12D 1.554(5)
C12D C13D 1.558(5)
C12D H12G 0.9900
C12D H12H 0.9900
C13D C14D 1.630(5)
C14D O6D 1.420(4)
C14D O5D 1.421(4)
C14D C15D 1.497(5)
C15D H15J 0.9800
C15D H15K 0.9800
C15D H15L 0.9800
C16D O2D 1.479(4)
C16D C18D 1.517(5)
C16D C17D 1.521(5)
C17D H17J 0.9800
C17D H17K 0.9800
C17D H17L 0.9800
C18D H18J 0.9800
C18D H18K 0.9800
C18D H18L 0.9800
C19D H19J 0.9800
C19D H19K 0.9800
C19D H19L 0.9800
C20D O7D 1.196(5)
C20D O8D 1.358(5)
C21D O9D 1.421(4)
C21D C22D 1.452(5)
C22D O9D 1.458(4)
C22D H22G 0.9900
C22D H22H 0.9900
C23D O8D 1.469(5)
C23D C24D 1.516(6)
C23D H23D 1.0000
C24D H24J 0.9800
C24D H24K 0.9800
C24D H24L 0.9800
C25D H25J 0.9800
C25D H25K 0.9800
C25D H25L 0.9800
O4D H4OD 0.74(6)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 167.4(4)
O2 C1 C2 C3 -7.9(5)
C1 C2 C3 C4 8.2(5)
C1 C2 C3 C13 -172.9(3)
C2 C3 C4 O3 -121.5(4)
C13 C3 C4 O3 59.5(4)
C2 C3 C4 C5 171.9(3)
C13 C3 C4 C5 -7.1(5)
C2 C3 C4 C16 18.4(5)
C13 C3 C4 C16 -160.5(3)
C3 C4 C5 O3 102.0(3)
C16 C4 C5 O3 -105.2(3)
O3 C4 C5 C6 -105.1(4)
C3 C4 C5 C6 -3.1(5)
C16 C4 C5 C6 149.6(3)
O3 C5 C6 C7 -87.5(4)
C4 C5 C6 C7 -19.0(5)
C5 C6 C7 C19 -71.0(4)
C5 C6 C7 C8 167.4(3)
C5 C6 C7 C13 50.2(4)
C6 C7 C8 C20 39.9(4)
C19 C7 C8 C20 -78.0(4)
C13 C7 C8 C20 161.8(3)
C6 C7 C8 C21 171.2(3)
C19 C7 C8 C21 53.2(4)
C13 C7 C8 C21 -67.0(3)
C6 C7 C8 C9 -77.1(3)
C19 C7 C8 C9 164.9(3)
C13 C7 C8 C9 44.7(3)
C20 C8 C9 O6 -103.2(3)
C21 C8 C9 O6 137.8(3)
C7 C8 C9 O6 19.8(4)
C20 C8 C9 C23 15.0(4)
C21 C8 C9 C23 -104.0(3)
C7 C8 C9 C23 138.0(3)
C20 C8 C9 C10 146.5(3)
C21 C8 C9 C10 27.5(3)
C7 C8 C9 C10 -90.5(3)
O6 C9 C10 O4 115.5(3)
C23 C9 C10 O4 -7.9(5)
C8 C9 C10 O4 -128.4(3)
O6 C9 C10 O5 -3.6(3)
C23 C9 C10 O5 -127.0(3)
C8 C9 C10 O5 112.5(3)
O6 C9 C10 C11 -115.8(3)
C23 C9 C10 C11 120.8(3)
C8 C9 C10 C11 0.3(4)
O4 C10 C11 C25 -26.7(4)
O5 C10 C11 C25 98.4(3)
C9 C10 C11 C25 -152.4(3)
O4 C10 C11 C21 97.8(3)
O5 C10 C11 C21 -137.1(3)
C9 C10 C11 C21 -28.0(3)
O4 C10 C11 C12 -149.9(3)
O5 C10 C11 C12 -24.8(4)
C9 C10 C11 C12 84.3(3)
C25 C11 C12 C13 -170.1(3)
C21 C11 C12 C13 63.0(4)
C10 C11 C12 C13 -44.5(4)
C2 C3 C13 C12 -22.9(5)
C4 C3 C13 C12 156.0(3)
C2 C3 C13 C7 -142.3(3)
C4 C3 C13 C7 36.6(4)
C2 C3 C13 C14 94.9(4)
C4 C3 C13 C14 -86.2(4)
C11 C12 C13 C3 -179.1(3)
C11 C12 C13 C7 -59.3(4)
C11 C12 C13 C14 58.5(3)
C6 C7 C13 C3 -58.5(4)
C19 C7 C13 C3 59.3(4)
C8 C7 C13 C3 179.8(3)
C6 C7 C13 C12 179.8(3)
C19 C7 C13 C12 -62.4(4)
C8 C7 C13 C12 58.1(3)
C6 C7 C13 C14 65.7(4)
C19 C7 C13 C14 -176.5(3)
C8 C7 C13 C14 -56.1(3)
C3 C13 C14 O6 124.5(3)
C12 C13 C14 O6 -113.7(3)
C7 C13 C14 O6 2.6(4)
C3 C13 C14 O5 -125.0(3)
C12 C13 C14 O5 -3.1(3)
C7 C13 C14 O5 113.1(3)
C3 C13 C14 C15 -1.8(4)
C12 C13 C14 C15 120.0(3)
C7 C13 C14 C15 -123.8(3)
O3 C4 C16 O2 96.1(3)
C5 C4 C16 O2 163.4(3)
C3 C4 C16 O2 -42.9(4)
O3 C4 C16 C17 -145.2(3)
C5 C4 C16 C17 -77.9(4)
C3 C4 C16 C17 75.8(4)
O3 C4 C16 C18 -18.2(4)
C5 C4 C16 C18 49.1(4)
C3 C4 C16 C18 -157.2(3)
C21 C8 C20 O7 -75.5(5)
C9 C8 C20 O7 174.9(4)
C7 C8 C20 O7 54.2(5)
C21 C8 C20 O8 105.6(3)
C9 C8 C20 O8 -4.1(4)
C7 C8 C20 O8 -124.8(3)
C25 C11 C21 O9 -51.0(4)
C12 C11 C21 O9 73.4(4)
C10 C11 C21 O9 -175.0(3)
C25 C11 C21 C22 21.4(5)
C12 C11 C21 C22 145.8(3)
C10 C11 C21 C22 -102.6(4)
C25 C11 C21 C8 170.8(3)
C12 C11 C21 C8 -64.8(3)
C10 C11 C21 C8 46.8(3)
C20 C8 C21 O9 64.2(4)
C9 C8 C21 O9 175.6(3)
C7 C8 C21 O9 -66.8(4)
C20 C8 C21 C22 -8.7(5)
C9 C8 C21 C22 102.7(4)
C7 C8 C21 C22 -139.7(3)
C20 C8 C21 C11 -158.2(3)
C9 C8 C21 C11 -46.8(3)
C7 C8 C21 C11 70.8(3)
C11 C21 C22 O9 -107.4(4)
C8 C21 C22 O9 109.1(4)
O6 C9 C23 O8 99.3(3)
C8 C9 C23 O8 -20.0(4)
C10 C9 C23 O8 -140.4(3)
O6 C9 C23 C24 -140.8(3)
C8 C9 C23 C24 99.9(4)
C10 C9 C23 C24 -20.5(5)
O1 C1 O2 C16 163.1(3)
C2 C1 O2 C16 -21.4(5)
C17 C16 O2 C1 -76.4(4)
C18 C16 O2 C1 165.5(3)
C4 C16 O2 C1 45.0(4)
C6 C5 O3 C4 111.5(3)
C3 C4 O3 C5 -111.1(3)
C16 C4 O3 C5 109.2(3)
O6 C14 O5 C10 49.5(3)
C15 C14 O5 C10 165.4(3)
C13 C14 O5 C10 -65.7(3)
O4 C10 O5 C14 -147.4(3)
C11 C10 O5 C14 83.6(3)
C9 C10 O5 C14 -27.1(3)
O5 C14 O6 C9 -51.9(3)
C15 C14 O6 C9 -166.0(3)
C13 C14 O6 C9 63.5(3)
C23 C9 O6 C14 165.1(3)
C8 C9 O6 C14 -79.1(3)
C10 C9 O6 C14 32.9(3)
O7 C20 O8 C23 171.5(3)
C8 C20 O8 C23 -9.4(4)
C24 C23 O8 C20 -110.2(3)
C9 C23 O8 C20 18.7(4)
C11 C21 O9 C22 114.8(4)
C8 C21 O9 C22 -114.0(4)
O1B C1B C2B C3B 158.3(4)
O2B C1B C2B C3B -17.7(5)
C1B C2B C3B C4B 10.0(5)
C1B C2B C3B C13B -168.6(3)
C2B C3B C4B O3B -114.3(4)
C13B C3B C4B O3B 64.3(4)
C2B C3B C4B C5B 178.9(3)
C13B C3B C4B C5B -2.4(5)
C2B C3B C4B C16B 23.2(5)
C13B C3B C4B C16B -158.2(3)
C3B C4B C5B O3B 102.0(3)
C16B C4B C5B O3B -103.5(4)
O3B C4B C5B C6B -105.0(4)
C3B C4B C5B C6B -3.0(5)
C16B C4B C5B C6B 151.4(3)
O3B C5B C6B C7B -92.1(4)
C4B C5B C6B C7B -22.5(5)
C5B C6B C7B C19B -69.5(4)
C5B C6B C7B C8B 169.5(3)
C5B C6B C7B C13B 53.1(4)
C19B C7B C8B C20B -78.7(4)
C6B C7B C8B C20B 39.5(4)
C13B C7B C8B C20B 160.8(3)
C19B C7B C8B C21B 53.2(4)
C6B C7B C8B C21B 171.5(3)
C13B C7B C8B C21B -67.2(4)
C19B C7B C8B C9B 163.8(3)
C6B C7B C8B C9B -78.0(4)
C13B C7B C8B C9B 43.3(4)
C20B C8B C9B O6B -101.9(3)
C21B C8B C9B O6B 138.6(3)
C7B C8B C9B O6B 21.5(4)
C20B C8B C9B C23B 15.6(4)
C21B C8B C9B C23B -103.9(3)
C7B C8B C9B C23B 139.0(3)
C20B C8B C9B C10B 147.2(3)
C21B C8B C9B C10B 27.7(3)
C7B C8B C9B C10B -89.4(3)
O6B C9B C10B O4B 115.5(3)
C23B C9B C10B O4B -8.2(5)
C8B C9B C10B O4B -128.0(3)
O6B C9B C10B O5B -3.7(3)
C23B C9B C10B O5B -127.4(3)
C8B C9B C10B O5B 112.8(3)
O6B C9B C10B C11B -116.6(3)
C23B C9B C10B C11B 119.8(3)
C8B C9B C10B C11B 0.0(4)
O4B C10B C11B C25B -26.0(5)
O5B C10B C11B C25B 98.9(4)
C9B C10B C11B C25B -152.1(3)
O4B C10B C11B C21B 98.4(3)
O5B C10B C11B C21B -136.8(3)
C9B C10B C11B C21B -27.7(3)
O4B C10B C11B C12B -149.0(3)
O5B C10B C11B C12B -24.2(4)
C9B C10B C11B C12B 84.8(3)
C25B C11B C12B C13B -170.3(3)
C21B C11B C12B C13B 62.4(4)
C10B C11B C12B C13B -44.9(4)
C2B C3B C13B C12B -29.7(5)
C4B C3B C13B C12B 151.8(3)
C2B C3B C13B C7B -149.8(3)
C4B C3B C13B C7B 31.7(4)
C2B C3B C13B C14B 87.8(4)
C4B C3B C13B C14B -90.7(4)
C11B C12B C13B C3B 179.4(3)
C11B C12B C13B C7B -59.9(4)
C11B C12B C13B C14B 59.1(4)
C19B C7B C13B C3B 61.9(4)
C6B C7B C13B C3B -57.5(4)
C8B C7B C13B C3B -178.3(3)
C19B C7B C13B C12B -60.8(4)
C6B C7B C13B C12B 179.8(3)
C8B C7B C13B C12B 59.0(3)
C19B C7B C13B C14B -176.2(3)
C6B C7B C13B C14B 64.4(4)
C8B C7B C13B C14B -56.4(4)
C3B C13B C14B O5B -124.7(3)
C12B C13B C14B O5B -3.1(4)
C7B C13B C14B O5B 113.9(3)
C3B C13B C14B O6B 125.3(3)
C12B C13B C14B O6B -113.0(3)
C7B C13B C14B O6B 4.0(4)
C3B C13B C14B C15B -1.5(4)
C12B C13B C14B C15B 120.2(3)
C7B C13B C14B C15B -122.9(3)
O3B C4B C16B O2B 90.5(3)
C5B C4B C16B O2B 158.3(3)
C3B C4B C16B O2B -46.3(4)
O3B C4B C16B C18B -23.2(4)
C5B C4B C16B C18B 44.5(5)
C3B C4B C16B C18B -160.0(3)
O3B C4B C16B C17B -150.8(3)
C5B C4B C16B C17B -83.0(4)
C3B C4B C16B C17B 72.5(4)
C21B C8B C20B O7B -77.2(5)
C9B C8B C20B O7B 173.5(4)
C7B C8B C20B O7B 52.8(6)
C21B C8B C20B O8B 103.3(4)
C9B C8B C20B O8B -6.0(4)
C7B C8B C20B O8B -126.7(3)
C20B C8B C21B O9B 64.4(4)
C9B C8B C21B O9B 176.1(3)
C7B C8B C21B O9B -67.3(4)
C20B C8B C21B C22B -8.7(5)
C9B C8B C21B C22B 103.0(4)
C7B C8B C21B C22B -140.4(4)
C20B C8B C21B C11B -158.5(3)
C9B C8B C21B C11B -46.9(3)
C7B C8B C21B C11B 69.8(3)
C25B C11B C21B O9B -50.7(5)
C12B C11B C21B O9B 74.2(4)
C10B C11B C21B O9B -175.0(3)
C25B C11B C21B C22B 21.5(5)
C12B C11B C21B C22B 146.4(4)
C10B C11B C21B C22B -102.8(4)
C25B C11B C21B C8B 171.2(3)
C12B C11B C21B C8B -63.9(4)
C10B C11B C21B C8B 46.9(3)
C8B C21B C22B O9B 109.2(4)
C11B C21B C22B O9B -106.8(4)
O6B C9B C23B O8B 99.3(3)
C8B C9B C23B O8B -19.4(4)
C10B C9B C23B O8B -139.9(3)
O6B C9B C23B C24B -141.5(3)
C8B C9B C23B C24B 99.8(4)
C10B C9B C23B C24B -20.7(5)
O1B C1B O2B C16B 173.3(3)
C2B C1B O2B C16B -10.4(5)
C18B C16B O2B C1B 161.1(3)
C4B C16B O2B C1B 40.6(4)
C17B C16B O2B C1B -80.3(4)
C6B C5B O3B C4B 112.4(4)
C3B C4B O3B C5B -111.2(3)
C16B C4B O3B C5B 111.6(4)
O6B C14B O5B C10B 49.0(3)
C15B C14B O5B C10B 165.9(3)
C13B C14B O5B C10B -65.4(3)
O4B C10B O5B C14B -148.0(3)
C11B C10B O5B C14B 83.8(3)
C9B C10B O5B C14B -26.8(3)
C23B C9B O6B C14B 165.4(3)
C8B C9B O6B C14B -80.2(3)
C10B C9B O6B C14B 32.7(3)
O5B C14B O6B C9B -51.5(3)
C15B C14B O6B C9B -166.6(3)
C13B C14B O6B C9B 62.8(3)
O7B C20B O8B C23B 173.5(4)
C8B C20B O8B C23B -7.0(4)
C24B C23B O8B C20B -110.8(3)
C9B C23B O8B C20B 17.0(4)
C8B C21B O9B C22B -114.0(4)
C11B C21B O9B C22B 114.9(4)
O1C C1C C2C C3C 164.9(4)
O2C C1C C2C C3C -11.5(5)
C1C C2C C3C C4C 7.3(5)
C1C C2C C3C C13C -171.4(3)
C2C C3C C4C O3C -114.0(4)
C13C C3C C4C O3C 64.8(4)
C2C C3C C4C C5C 180.0(3)
C13C C3C C4C C5C -1.3(5)
C2C C3C C4C C16C 23.6(4)
C13C C3C C4C C16C -157.6(3)
C3C C4C C5C O3C 101.0(3)
C16C C4C C5C O3C -104.0(4)
O3C C4C C5C C6C -105.1(4)
C3C C4C C5C C6C -4.1(5)
C16C C4C C5C C6C 150.8(3)
O3C C5C C6C C7C -91.4(4)
C4C C5C C6C C7C -21.7(5)
C5C C6C C7C C19C -69.6(4)
C5C C6C C7C C8C 170.5(3)
C5C C6C C7C C13C 52.8(4)
C19C C7C C8C C20C -77.1(4)
C6C C7C C8C C20C 40.1(4)
C13C C7C C8C C20C 162.0(3)
C19C C7C C8C C21C 53.6(4)
C6C C7C C8C C21C 170.8(3)
C13C C7C C8C C21C -67.2(3)
C19C C7C C8C C9C 163.9(3)
C6C C7C C8C C9C -79.0(4)
C13C C7C C8C C9C 43.0(4)
C20C C8C C9C O6C -104.1(3)
C21C C8C C9C O6C 138.4(3)
C7C C8C C9C O6C 21.4(4)
C20C C8C C9C C23C 12.5(4)
C21C C8C C9C C23C -105.0(3)
C7C C8C C9C C23C 138.0(3)
C20C C8C C9C C10C 145.3(3)
C21C C8C C9C C10C 27.8(3)
C7C C8C C9C C10C -89.2(3)
O6C C9C C10C O4C 118.0(3)
C8C C9C C10C O4C -125.5(3)
C23C C9C C10C O4C -4.9(5)
O6C C9C C10C O5C -2.8(3)
C8C C9C C10C O5C 113.6(3)
C23C C9C C10C O5C -125.8(3)
O6C C9C C10C C11C -116.6(3)
C8C C9C C10C C11C -0.1(3)
C23C C9C C10C C11C 120.5(3)
O4C C10C C11C C21C 101.8(3)
O5C C10C C11C C21C -136.5(3)
C9C C10C C11C C21C -28.3(3)
O4C C10C C11C C25C -22.9(4)
O5C C10C C11C C25C 98.8(3)
C9C C10C C11C C25C -153.0(3)
O4C C10C C11C C12C -144.1(3)
O5C C10C C11C C12C -22.4(4)
C9C C10C C11C C12C 85.8(3)
C21C C11C C12C C13C 61.8(4)
C25C C11C C12C C13C -170.6(3)
C10C C11C C12C C13C -46.3(4)
C2C C3C C13C C12C -31.0(5)
C4C C3C C13C C12C 150.3(3)
C2C C3C C13C C7C -150.2(3)
C4C C3C C13C C7C 31.2(4)
C2C C3C C13C C14C 86.8(4)
C4C C3C C13C C14C -91.8(3)
C11C C12C C13C C3C -179.2(3)
C11C C12C C13C C7C -58.9(4)
C11C C12C C13C C14C 59.9(3)
C19C C7C C13C C3C 61.4(4)
C8C C7C C13C C3C -179.0(3)
C6C C7C C13C C3C -57.3(4)
C19C C7C C13C C12C -60.0(4)
C8C C7C C13C C12C 59.6(3)
C6C C7C C13C C12C -178.8(3)
C19C C7C C13C C14C -175.6(3)
C8C C7C C13C C14C -56.0(3)
C6C C7C C13C C14C 65.7(4)
C3C C13C C14C O6C 125.4(3)
C12C C13C C14C O6C -113.3(3)
C7C C13C C14C O6C 3.3(4)
C3C C13C C14C O5C -124.2(3)
C12C C13C C14C O5C -3.0(3)
C7C C13C C14C O5C 113.7(3)
C3C C13C C14C C15C -0.9(4)
C12C C13C C14C C15C 120.4(3)
C7C C13C C14C C15C -123.0(3)
O3C C4C C16C O2C 88.5(3)
C5C C4C C16C O2C 156.1(3)
C3C C4C C16C O2C -47.8(4)
O3C C4C C16C C18C -26.2(4)
C5C C4C C16C C18C 41.5(5)
C3C C4C C16C C18C -162.5(3)
O3C C4C C16C C17C -153.5(3)
C5C C4C C16C C17C -85.9(4)
C3C C4C C16C C17C 70.2(4)
C21C C8C C20C O7C -79.7(5)
C9C C8C C20C O7C 171.8(4)
C7C C8C C20C O7C 50.0(5)
C21C C8C C20C O8C 99.8(3)
C9C C8C C20C O8C -8.8(4)
C7C C8C C20C O8C -130.6(3)
C25C C11C C21C O9C -48.3(5)
C10C C11C C21C O9C -172.8(3)
C12C C11C C21C O9C 76.3(4)
C25C C11C C21C C22C 23.8(5)
C10C C11C C21C C22C -100.7(4)
C12C C11C C21C C22C 148.5(3)
C25C C11C C21C C8C 172.4(3)
C10C C11C C21C C8C 47.9(3)
C12C C11C C21C C8C -63.0(3)
C20C C8C C21C O9C 61.4(4)
C9C C8C C21C O9C 172.8(3)
C7C C8C C21C O9C -70.8(4)
C20C C8C C21C C22C -10.4(5)
C9C C8C C21C C22C 101.0(4)
C7C C8C C21C C22C -142.6(3)
C20C C8C C21C C11C -159.2(3)
C9C C8C C21C C11C -47.8(3)
C7C C8C C21C C11C 68.6(3)
C11C C21C C22C O9C -108.5(4)
C8C C21C C22C O9C 108.7(4)
O6C C9C C23C O8C 106.8(3)
C8C C9C C23C O8C -11.9(4)
C10C C9C C23C O8C -132.6(3)
O6C C9C C23C C24C -132.7(3)
C8C C9C C23C C24C 108.6(4)
C10C C9C C23C C24C -12.1(5)
O1C C1C O2C C16C 166.0(3)
C2C C1C O2C C16C -17.4(5)
C4C C16C O2C C1C 45.4(4)
C18C C16C O2C C1C 166.5(3)
C17C C16C O2C C1C -75.3(4)
C6C C5C O3C C4C 112.3(4)
C3C C4C O3C C5C -111.4(3)
C16C C4C O3C C5C 111.6(3)
O6C C14C O5C C10C 49.7(3)
C15C C14C O5C C10C 166.1(3)
C13C C14C O5C C10C -64.7(3)
O4C C10C O5C C14C -154.4(3)
C11C C10C O5C C14C 83.0(3)
C9C C10C O5C C14C -27.3(3)
O5C C14C O6C C9C -51.4(3)
C15C C14C O6C C9C -166.5(3)
C13C C14C O6C C9C 62.6(3)
C8C C9C O6C C14C -79.9(3)
C23C C9C O6C C14C 165.4(3)
C10C C9C O6C C14C 32.0(3)
O7C C20C O8C C23C -179.5(3)
C8C C20C O8C C23C 1.0(4)
C24C C23C O8C C20C -121.2(3)
C9C C23C O8C C20C 7.1(4)
C11C C21C O9C C22C 114.0(4)
C8C C21C O9C C22C -113.1(4)
O1D C1D C2D C3D 156.2(3)
O2D C1D C2D C3D -19.9(5)
C1D C2D C3D C4D 8.8(5)
C1D C2D C3D C13D -166.1(3)
C2D C3D C4D O3D -109.2(4)
C13D C3D C4D O3D 65.9(4)
C2D C3D C4D C5D -175.4(3)
C13D C3D C4D C5D -0.2(5)
C2D C3D C4D C16D 28.0(4)
C13D C3D C4D C16D -156.9(3)
C3D C4D C5D O3D 100.6(3)
C16D C4D C5D O3D -104.6(4)
O3D C4D C5D C6D -104.6(4)
C3D C4D C5D C6D -4.0(5)
C16D C4D C5D C6D 150.8(3)
O3D C5D C6D C7D -91.3(4)
C4D C5D C6D C7D -22.2(5)
C5D C6D C7D C19D -69.1(4)
C5D C6D C7D C8D 169.9(3)
C5D C6D C7D C13D 52.3(4)
C19D C7D C8D C20D -77.6(4)
C6D C7D C8D C20D 39.3(4)
C13D C7D C8D C20D 161.3(3)
C19D C7D C8D C21D 52.6(4)
C6D C7D C8D C21D 169.5(3)
C13D C7D C8D C21D -68.5(3)
C19D C7D C8D C9D 163.7(3)
C6D C7D C8D C9D -79.4(3)
C13D C7D C8D C9D 42.6(4)
C20D C8D C9D O6D -103.4(3)
C21D C8D C9D O6D 139.0(3)
C7D C8D C9D O6D 21.3(4)
C20D C8D C9D C23D 14.3(4)
C21D C8D C9D C23D -103.3(3)
C7D C8D C9D C23D 139.0(3)
C20D C8D C9D C10D 146.5(3)
C21D C8D C9D C10D 28.9(3)
C7D C8D C9D C10D -88.8(3)
O6D C9D C10D O4D 117.4(3)
C8D C9D C10D O4D -126.7(3)
C23D C9D C10D O4D -5.8(5)
O6D C9D C10D O5D -3.2(3)
C8D C9D C10D O5D 112.7(3)
C23D C9D C10D O5D -126.3(3)
O6D C9D C10D C11D -116.4(3)
C8D C9D C10D C11D -0.5(4)
C23D C9D C10D C11D 120.4(4)
O4D C10D C11D C21D 101.4(3)
O5D C10D C11D C21D -136.9(3)
C9D C10D C11D C21D -28.4(3)
O4D C10D C11D C25D -22.2(4)
O5D C10D C11D C25D 99.6(4)
C9D C10D C11D C25D -152.0(3)
O4D C10D C11D C12D -144.6(3)
O5D C10D C11D C12D -22.9(4)
C9D C10D C11D C12D 85.6(3)
C21D C11D C12D C13D 62.1(4)
C25D C11D C12D C13D -171.3(3)
C10D C11D C12D C13D -45.9(4)
C2D C3D C13D C12D -36.2(5)
C4D C3D C13D C12D 149.1(3)
C2D C3D C13D C7D -155.8(3)
C4D C3D C13D C7D 29.5(4)
C2D C3D C13D C14D 80.8(4)
C4D C3D C13D C14D -94.0(4)
C11D C12D C13D C3D 179.4(3)
C11D C12D C13D C7D -59.3(4)
C11D C12D C13D C14D 59.0(3)
C19D C7D C13D C3D 61.4(4)
C8D C7D C13D C3D -177.6(3)
C6D C7D C13D C3D -55.9(4)
C19D C7D C13D C12D -60.8(4)
C8D C7D C13D C12D 60.1(3)
C6D C7D C13D C12D -178.1(3)
C19D C7D C13D C14D -175.3(3)
C8D C7D C13D C14D -54.3(3)
C6D C7D C13D C14D 67.5(4)
C3D C13D C14D O6D 125.2(3)
C12D C13D C14D O6D -113.8(3)
C7D C13D C14D O6D 2.1(4)
C3D C13D C14D O5D -124.0(3)
C12D C13D C14D O5D -3.0(4)
C7D C13D C14D O5D 112.9(3)
C3D C13D C14D C15D -0.3(4)
C12D C13D C14D C15D 120.8(3)
C7D C13D C14D C15D -123.3(3)
O3D C4D C16D O2D 83.6(3)
C5D C4D C16D O2D 152.0(3)
C3D C4D C16D O2D -51.8(4)
O3D C4D C16D C18D -29.8(4)
C5D C4D C16D C18D 38.7(5)
C3D C4D C16D C18D -165.2(3)
O3D C4D C16D C17D -157.1(3)
C5D C4D C16D C17D -88.6(4)
C3D C4D C16D C17D 67.5(4)
C21D C8D C20D O7D -78.9(5)
C9D C8D C20D O7D 172.7(4)
C7D C8D C20D O7D 50.2(5)
C21D C8D C20D O8D 100.9(3)
C9D C8D C20D O8D -7.5(4)
C7D C8D C20D O8D -130.0(3)
C25D C11D C21D O9D -49.7(5)
C10D C11D C21D O9D -173.8(3)
C12D C11D C21D O9D 74.8(4)
C25D C11D C21D C22D 24.5(5)
C10D C11D C21D C22D -99.6(4)
C12D C11D C21D C22D 149.0(3)
C25D C11D C21D C8D 172.5(3)
C10D C11D C21D C8D 48.3(3)
C12D C11D C21D C8D -63.1(3)
C20D C8D C21D O9D 62.1(4)
C9D C8D C21D O9D 173.1(3)
C7D C8D C21D O9D -69.0(4)
C20D C8D C21D C22D -10.8(5)
C9D C8D C21D C22D 100.2(4)
C7D C8D C21D C22D -141.9(3)
C20D C8D C21D C11D -159.7(3)
C9D C8D C21D C11D -48.7(3)
C7D C8D C21D C11D 69.3(3)
C11D C21D C22D O9D -109.0(4)
C8D C21D C22D O9D 108.9(4)
O6D C9D C23D O8D 103.0(3)
C8D C9D C23D O8D -15.8(4)
C10D C9D C23D O8D -136.7(3)
O6D C9D C23D C24D -136.2(3)
C8D C9D C23D C24D 104.9(4)
C10D C9D C23D C24D -16.0(5)
O1D C1D O2D C16D 174.9(3)
C2D C1D O2D C16D -8.8(5)
C4D C16D O2D C1D 42.8(4)
C18D C16D O2D C1D 163.1(3)
C17D C16D O2D C1D -79.6(4)
C6D C5D O3D C4D 112.0(4)
C3D C4D O3D C5D -111.8(3)
C16D C4D O3D C5D 112.5(4)
O6D C14D O5D C10D 49.8(3)
C15D C14D O5D C10D 165.4(3)
C13D C14D O5D C10D -65.4(3)
O4D C10D O5D C14D -153.7(3)
C11D C10D O5D C14D 82.9(3)
C9D C10D O5D C14D -27.3(3)
C8D C9D O6D C14D -79.5(3)
C23D C9D O6D C14D 164.9(3)
C10D C9D O6D C14D 32.4(3)
O5D C14D O6D C9D -51.7(3)
C15D C14D O6D C9D -166.4(3)
C13D C14D O6D C9D 63.5(3)
O7D C20D O8D C23D 176.9(3)
C8D C20D O8D C23D -2.9(4)
C24D C23D O8D C20D -116.5(3)
C9D C23D O8D C20D 12.0(4)
C11D C21D O9D C22D 115.6(4)
C8D C21D O9D C22D -113.3(4)
|
1501998.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501998.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501998
loop_
_publ_author_name
'Xia, Bing'
'Gerard, Baudouin'
'Solano, Danielle M.'
'Wan, Jiandi'
'Jones, 2nd, Guilford'
'Porco, Jr, John A'
_publ_section_title
;
ESIPT-mediated photocycloadditions of 3-hydroxyquinolinones: development
of a fluorescence quenching assay for reaction screening.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1346
_journal_page_last 1349
_journal_paper_doi 10.1021/ol200032f
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C29 H27 Br2 N O5'
_chemical_formula_sum 'C29 H27 Br2 N O5'
_chemical_formula_weight 629.34
_chemical_name_systematic
;
?
;
_space_group_IT_number 7
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P -2yac'
_symmetry_space_group_name_H-M 'P 1 n 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 98.976(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.5231(4)
_cell_length_b 29.4273(12)
_cell_length_c 11.1098(5)
_cell_measurement_reflns_used 3088
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 22.73
_cell_measurement_theta_min 2.32
_cell_volume 2752.3(2)
_computing_cell_refinement 'Bruker SAINT+'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT+'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0448
_diffrn_reflns_av_sigmaI/netI 0.0985
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 34
_diffrn_reflns_limit_k_min -30
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 21890
_diffrn_reflns_theta_full 24.40
_diffrn_reflns_theta_max 24.40
_diffrn_reflns_theta_min 1.38
_exptl_absorpt_coefficient_mu 2.984
_exptl_absorpt_correction_T_max 0.4680
_exptl_absorpt_correction_T_min 0.3169
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.519
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1272
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.30
_refine_diff_density_max 0.402
_refine_diff_density_min -0.569
_refine_diff_density_rms 0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.020(8)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 675
_refine_ls_number_reflns 8741
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.052
_refine_ls_R_factor_all 0.0869
_refine_ls_R_factor_gt 0.0471
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0125P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0985
_refine_ls_wR_factor_ref 0.1118
_reflns_number_gt 6045
_reflns_number_total 8741
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200032f_si_002.cif
_cod_data_source_block porco70
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M Pn
_cod_database_code 1501998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.39494(10) 0.69338(2) 0.62044(7) 0.0710(3) Uani 1 1 d .
Br2 Br 0.48856(12) 1.27880(3) 1.31663(8) 0.0970(4) Uani 1 1 d .
O1 O 0.3368(4) 1.01375(12) 1.0640(3) 0.0272(9) Uani 1 1 d .
O2 O 0.6600(4) 0.90163(11) 0.8166(3) 0.0283(9) Uani 1 1 d .
O3 O 0.7486(4) 0.90129(12) 0.6376(3) 0.0359(10) Uani 1 1 d .
O4 O 0.6434(4) 1.06811(11) 1.1250(3) 0.0238(8) Uani 1 1 d .
O5 O 0.6122(4) 1.04981(12) 1.3157(3) 0.0278(9) Uani 1 1 d .
N1 N 0.7407(5) 1.04169(14) 0.9066(4) 0.0215(10) Uani 1 1 d .
C1 C 0.4698(6) 1.01413(17) 1.0012(4) 0.0195(12) Uani 1 1 d .
C2 C 0.4586(6) 1.04923(17) 0.9029(4) 0.0221(13) Uani 1 1 d .
C3 C 0.3172(6) 1.07019(17) 0.8567(5) 0.0263(13) Uani 1 1 d .
H3A H 0.2238 1.0626 0.8891 0.032 Uiso 1 1 calc R
C4 C 0.3083(7) 1.10189(19) 0.7646(5) 0.0357(15) Uani 1 1 d .
H4A H 0.2096 1.1160 0.7347 0.043 Uiso 1 1 calc R
C5 C 0.4424(7) 1.11326(18) 0.7155(5) 0.0349(15) Uani 1 1 d .
H5A H 0.4366 1.1347 0.6509 0.042 Uiso 1 1 calc R
C6 C 0.5865(7) 1.09268(17) 0.7626(5) 0.0283(13) Uani 1 1 d .
H6A H 0.6794 1.1006 0.7298 0.034 Uiso 1 1 calc R
C7 C 0.5978(6) 1.06103(17) 0.8560(4) 0.0214(12) Uani 1 1 d .
C8 C 0.7475(6) 1.00814(18) 1.0032(4) 0.0215(12) Uani 1 1 d .
C9 C 0.6260(6) 1.02176(16) 1.0851(4) 0.0206(12) Uani 1 1 d .
H9A H 0.6341 1.0010 1.1570 0.025 Uiso 1 1 calc R
C10 C 0.8760(6) 1.04908(19) 0.8435(5) 0.0331(15) Uani 1 1 d .
H10A H 0.8448 1.0428 0.7564 0.050 Uiso 1 1 calc R
H10B H 0.9629 1.0287 0.8771 0.050 Uiso 1 1 calc R
H10C H 0.9113 1.0807 0.8544 0.050 Uiso 1 1 calc R
C11 C 0.4259(6) 0.92790(17) 1.0195(5) 0.0263(13) Uani 1 1 d .
H11A H 0.3105 0.9315 1.0129 0.040 Uiso 1 1 calc R
H11B H 0.4742 0.9290 1.1055 0.040 Uiso 1 1 calc R
H11C H 0.4498 0.8986 0.9844 0.040 Uiso 1 1 calc R
C12 C 0.4929(6) 0.96618(17) 0.9506(5) 0.0198(12) Uani 1 1 d .
H12A H 0.4426 0.9650 0.8631 0.024 Uiso 1 1 calc R
C13 C 0.6774(6) 0.96180(16) 0.9585(4) 0.0183(12) Uani 1 1 d .
H13A H 0.7157 0.9386 1.0220 0.022 Uiso 1 1 calc R
C14 C 0.7274(6) 0.94700(17) 0.8406(5) 0.0240(13) Uani 1 1 d .
H14A H 0.6857 0.9681 0.7739 0.029 Uiso 1 1 calc R
H14B H 0.8446 0.9460 0.8483 0.029 Uiso 1 1 calc R
C15 C 0.6801(6) 0.88280(19) 0.7121(5) 0.0294(14) Uani 1 1 d .
C16 C 0.6125(6) 0.83698(18) 0.6953(5) 0.0286(13) Uani 1 1 d .
C17 C 0.6387(8) 0.8119(2) 0.5936(6) 0.0489(17) Uani 1 1 d .
H17A H 0.7021 0.8247 0.5390 0.059 Uiso 1 1 calc R
C18 C 0.5754(8) 0.7694(2) 0.5705(6) 0.0551(19) Uani 1 1 d .
H18A H 0.5925 0.7528 0.5004 0.066 Uiso 1 1 calc R
C19 C 0.4862(8) 0.7516(2) 0.6524(6) 0.0458(17) Uani 1 1 d .
C20 C 0.4615(8) 0.7744(2) 0.7547(6) 0.0465(17) Uani 1 1 d .
H20A H 0.4017 0.7608 0.8105 0.056 Uiso 1 1 calc R
C21 C 0.5242(7) 0.81726(19) 0.7763(5) 0.0372(15) Uani 1 1 d .
H21A H 0.5069 0.8334 0.8470 0.045 Uiso 1 1 calc R
C22 C 0.9138(6) 1.00425(18) 1.0778(4) 0.0281(13) Uani 1 1 d .
H22A H 0.9898 0.9959 1.0239 0.042 Uiso 1 1 calc R
H22B H 0.9135 0.9809 1.1406 0.042 Uiso 1 1 calc R
H22C H 0.9444 1.0335 1.1165 0.042 Uiso 1 1 calc R
C23 C 0.6200(6) 1.07815(18) 1.2384(5) 0.0217(12) Uani 1 1 d .
C24 C 0.5984(6) 1.12668(19) 1.2557(5) 0.0299(14) Uani 1 1 d .
C25 C 0.5756(7) 1.1421(2) 1.3701(5) 0.0393(15) Uani 1 1 d .
H25A H 0.5816 1.1214 1.4362 0.047 Uiso 1 1 calc R
C26 C 0.5443(8) 1.1871(2) 1.3874(6) 0.0510(18) Uani 1 1 d .
H26A H 0.5281 1.1978 1.4652 0.061 Uiso 1 1 calc R
C27 C 0.5367(8) 1.2163(2) 1.2924(7) 0.0529(19) Uani 1 1 d .
C28 C 0.5608(8) 1.2028(2) 1.1795(6) 0.0509(18) Uani 1 1 d .
H28A H 0.5564 1.2240 1.1148 0.061 Uiso 1 1 calc R
C29 C 0.5914(7) 1.1582(2) 1.1614(5) 0.0389(15) Uani 1 1 d .
H29A H 0.6083 1.1483 1.0830 0.047 Uiso 1 1 calc R
Br3 Br 0.40769(11) 0.81616(2) 0.14415(8) 0.0801(3) Uani 1 1 d .
Br4 Br 0.45057(12) 0.22127(2) 0.82291(7) 0.0911(4) Uani 1 1 d .
O6 O 0.2552(4) 0.48826(12) 0.5678(3) 0.0279(9) Uani 1 1 d .
O7 O 0.5649(4) 0.43404(11) 0.6278(3) 0.0256(9) Uani 1 1 d .
O8 O 0.5256(4) 0.45245(12) 0.8172(3) 0.0261(9) Uani 1 1 d .
O9 O 0.5803(4) 0.59863(11) 0.3126(3) 0.0294(9) Uani 1 1 d .
O10 O 0.6738(5) 0.59812(13) 0.1356(3) 0.0396(11) Uani 1 1 d .
N2 N 0.6555(5) 0.45894(14) 0.4073(4) 0.0224(11) Uani 1 1 d .
C30 C 0.3891(6) 0.48790(17) 0.5046(4) 0.0215(13) Uani 1 1 d .
C31 C 0.3727(6) 0.45210(17) 0.4075(4) 0.0214(12) Uani 1 1 d .
C32 C 0.2298(6) 0.43127(18) 0.3615(5) 0.0292(14) Uani 1 1 d .
H32A H 0.1361 0.4397 0.3922 0.035 Uiso 1 1 calc R
C33 C 0.2215(7) 0.39899(19) 0.2733(5) 0.0353(15) Uani 1 1 d .
H33A H 0.1225 0.3849 0.2441 0.042 Uiso 1 1 calc R
C34 C 0.3543(7) 0.38641(19) 0.2258(5) 0.0371(15) Uani 1 1 d .
H34A H 0.3467 0.3643 0.1630 0.045 Uiso 1 1 calc R
C35 C 0.5004(7) 0.40627(18) 0.2702(5) 0.0319(14) Uani 1 1 d .
H35A H 0.5927 0.3971 0.2386 0.038 Uiso 1 1 calc R
C36 C 0.5120(6) 0.43929(17) 0.3601(5) 0.0246(13) Uani 1 1 d .
C37 C 0.6651(6) 0.49272(17) 0.5035(4) 0.0215(12) Uani 1 1 d .
C38 C 0.5448(6) 0.48052(16) 0.5883(5) 0.0220(12) Uani 1 1 d .
H38A H 0.5550 0.5016 0.6597 0.026 Uiso 1 1 calc R
C39 C 0.7918(6) 0.4502(2) 0.3456(5) 0.0354(15) Uani 1 1 d .
H39A H 0.8260 0.4186 0.3594 0.053 Uiso 1 1 calc R
H39B H 0.8791 0.4706 0.3781 0.053 Uiso 1 1 calc R
H39C H 0.7616 0.4555 0.2580 0.053 Uiso 1 1 calc R
C40 C 0.3459(6) 0.57366(18) 0.5214(5) 0.0319(14) Uani 1 1 d .
H40A H 0.2307 0.5700 0.5161 0.048 Uiso 1 1 calc R
H40B H 0.3689 0.6029 0.4854 0.048 Uiso 1 1 calc R
H40C H 0.3956 0.5729 0.6071 0.048 Uiso 1 1 calc R
C41 C 0.4113(6) 0.53542(17) 0.4528(5) 0.0215(12) Uani 1 1 d .
H41A H 0.3582 0.5362 0.3659 0.026 Uiso 1 1 calc R
C42 C 0.5931(6) 0.53901(18) 0.4557(5) 0.0229(13) Uani 1 1 d .
H42A H 0.6338 0.5627 0.5172 0.027 Uiso 1 1 calc R
C43 C 0.6414(6) 0.55253(18) 0.3372(5) 0.0267(14) Uani 1 1 d .
H43A H 0.7585 0.5520 0.3431 0.032 Uiso 1 1 calc R
H43B H 0.5952 0.5315 0.2715 0.032 Uiso 1 1 calc R
C44 C 0.6082(6) 0.61741(18) 0.2090(5) 0.0265(13) Uani 1 1 d .
C45 C 0.5539(7) 0.66481(18) 0.1960(5) 0.0317(14) Uani 1 1 d .
C46 C 0.5970(8) 0.6898(2) 0.1011(6) 0.0468(17) Uani 1 1 d .
H46A H 0.6574 0.6758 0.0465 0.056 Uiso 1 1 calc R
C47 C 0.5548(9) 0.7342(2) 0.0845(7) 0.061(2) Uani 1 1 d .
H47A H 0.5862 0.7514 0.0198 0.073 Uiso 1 1 calc R
C48 C 0.4645(8) 0.7539(2) 0.1646(7) 0.054(2) Uani 1 1 d .
C49 C 0.4190(7) 0.7303(2) 0.2595(6) 0.0481(17) Uani 1 1 d .
H49A H 0.3586 0.7444 0.3140 0.058 Uiso 1 1 calc R
C50 C 0.4635(7) 0.68521(19) 0.2737(5) 0.0385(16) Uani 1 1 d .
H50A H 0.4315 0.6680 0.3380 0.046 Uiso 1 1 calc R
C51 C 0.8322(6) 0.49716(19) 0.5766(5) 0.0311(14) Uani 1 1 d .
H51A H 0.9073 0.5051 0.5215 0.047 Uiso 1 1 calc R
H51B H 0.8637 0.4682 0.6168 0.047 Uiso 1 1 calc R
H51C H 0.8327 0.5210 0.6382 0.047 Uiso 1 1 calc R
C52 C 0.5390(6) 0.42435(18) 0.7416(5) 0.0241(13) Uani 1 1 d .
C53 C 0.5266(6) 0.37473(18) 0.7593(5) 0.0282(13) Uani 1 1 d .
C54 C 0.4969(7) 0.35927(19) 0.8725(5) 0.0341(14) Uani 1 1 d .
H54A H 0.4910 0.3804 0.9363 0.041 Uiso 1 1 calc R
C55 C 0.4762(8) 0.3137(2) 0.8919(6) 0.0485(18) Uani 1 1 d .
H55A H 0.4559 0.3031 0.9688 0.058 Uiso 1 1 calc R
C56 C 0.4851(9) 0.2842(2) 0.7996(6) 0.0529(19) Uani 1 1 d .
C57 C 0.5139(9) 0.2983(2) 0.6883(6) 0.0542(19) Uani 1 1 d .
H57A H 0.5192 0.2769 0.6251 0.065 Uiso 1 1 calc R
C58 C 0.5352(7) 0.3442(2) 0.6680(5) 0.0407(16) Uani 1 1 d .
H58A H 0.5558 0.3544 0.5908 0.049 Uiso 1 1 calc R
H6O H 0.239(7) 0.461(2) 0.600(5) 0.050 Uiso 1 1 d .
H1O H 0.321(8) 1.040(2) 1.089(6) 0.076 Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0991(6) 0.0303(4) 0.0775(6) -0.0124(4) -0.0053(5) -0.0223(5)
Br2 0.1807(11) 0.0342(5) 0.0730(6) -0.0108(4) 0.0096(7) 0.0388(6)
O1 0.023(2) 0.029(2) 0.033(2) -0.0014(18) 0.0167(18) -0.0036(18)
O2 0.038(2) 0.021(2) 0.027(2) -0.0090(17) 0.0107(18) -0.0077(17)
O3 0.048(3) 0.034(2) 0.030(2) -0.0070(19) 0.019(2) -0.009(2)
O4 0.033(2) 0.024(2) 0.0157(19) -0.0051(16) 0.0078(16) -0.0043(17)
O5 0.030(2) 0.029(2) 0.024(2) -0.0039(18) 0.0032(17) 0.0025(18)
N1 0.023(3) 0.022(3) 0.021(2) 0.001(2) 0.007(2) -0.010(2)
C1 0.020(3) 0.021(3) 0.018(3) -0.002(2) 0.004(2) -0.001(2)
C2 0.030(3) 0.015(3) 0.021(3) -0.001(2) 0.000(3) -0.002(2)
C3 0.024(3) 0.021(3) 0.033(3) -0.008(3) 0.000(3) 0.002(3)
C4 0.040(4) 0.025(3) 0.037(4) 0.000(3) -0.009(3) 0.015(3)
C5 0.054(4) 0.019(3) 0.029(3) 0.003(3) 0.000(3) -0.010(3)
C6 0.043(4) 0.019(3) 0.022(3) -0.003(3) 0.003(3) -0.010(3)
C7 0.028(3) 0.021(3) 0.015(3) -0.006(2) 0.003(2) 0.000(3)
C8 0.019(3) 0.028(3) 0.016(3) -0.007(2) -0.003(2) 0.001(2)
C9 0.033(3) 0.015(3) 0.015(3) -0.002(2) 0.006(2) 0.000(2)
C10 0.032(4) 0.038(4) 0.032(4) 0.000(3) 0.015(3) -0.009(3)
C11 0.034(3) 0.022(3) 0.025(3) -0.003(3) 0.011(3) -0.004(3)
C12 0.019(3) 0.023(3) 0.017(3) -0.001(2) 0.003(2) 0.001(2)
C13 0.025(3) 0.017(3) 0.014(3) 0.002(2) 0.006(2) 0.002(2)
C14 0.028(3) 0.022(3) 0.023(3) -0.001(3) 0.009(3) -0.002(3)
C15 0.033(4) 0.028(4) 0.026(3) 0.002(3) 0.003(3) 0.000(3)
C16 0.037(3) 0.021(3) 0.027(3) -0.008(3) 0.003(3) 0.002(3)
C17 0.059(4) 0.045(5) 0.047(4) -0.012(3) 0.022(3) -0.007(4)
C18 0.079(5) 0.033(4) 0.055(5) -0.023(4) 0.016(4) -0.016(4)
C19 0.057(4) 0.022(4) 0.054(5) -0.009(3) -0.003(4) -0.011(3)
C20 0.064(5) 0.027(4) 0.044(4) 0.003(3) -0.003(3) -0.017(3)
C21 0.053(4) 0.027(4) 0.033(3) -0.001(3) 0.010(3) -0.008(3)
C22 0.033(3) 0.023(3) 0.028(3) -0.004(2) 0.002(3) -0.001(3)
C23 0.019(3) 0.025(3) 0.021(3) -0.003(3) 0.004(2) -0.004(2)
C24 0.033(3) 0.027(3) 0.029(3) -0.004(3) 0.005(3) 0.011(3)
C25 0.055(4) 0.038(4) 0.024(3) -0.002(3) 0.003(3) 0.017(3)
C26 0.070(5) 0.045(5) 0.037(4) -0.011(3) 0.006(3) 0.021(4)
C27 0.071(5) 0.028(4) 0.056(5) -0.014(4) -0.003(4) 0.017(3)
C28 0.084(5) 0.031(4) 0.036(4) -0.003(3) 0.004(4) 0.004(4)
C29 0.051(4) 0.033(4) 0.031(4) 0.000(3) 0.002(3) 0.009(3)
Br3 0.0936(6) 0.0254(4) 0.1105(9) 0.0151(5) -0.0181(5) 0.0093(5)
Br4 0.1782(11) 0.0262(4) 0.0649(6) 0.0115(4) 0.0062(6) -0.0180(5)
O6 0.030(2) 0.023(2) 0.033(2) 0.0056(18) 0.0141(18) 0.0027(18)
O7 0.035(2) 0.024(2) 0.018(2) 0.0074(16) 0.0062(16) 0.0038(17)
O8 0.035(2) 0.024(2) 0.022(2) -0.0011(18) 0.0100(18) -0.0024(17)
O9 0.047(2) 0.014(2) 0.030(2) 0.0069(17) 0.0150(18) 0.0095(17)
O10 0.059(3) 0.033(2) 0.031(2) 0.002(2) 0.020(2) 0.008(2)
N2 0.020(3) 0.024(3) 0.026(3) 0.001(2) 0.012(2) 0.004(2)
C30 0.019(3) 0.027(3) 0.020(3) 0.003(2) 0.006(2) -0.004(2)
C31 0.028(3) 0.016(3) 0.021(3) 0.000(2) 0.005(2) 0.004(2)
C32 0.026(3) 0.029(4) 0.031(3) 0.003(3) 0.001(3) -0.004(3)
C33 0.035(4) 0.026(3) 0.041(4) 0.003(3) -0.009(3) -0.007(3)
C34 0.054(4) 0.023(3) 0.030(4) -0.004(3) -0.007(3) 0.001(3)
C35 0.035(4) 0.030(4) 0.029(3) -0.003(3) 0.002(3) 0.013(3)
C36 0.033(3) 0.019(3) 0.021(3) 0.005(2) 0.001(3) 0.003(3)
C37 0.025(3) 0.020(3) 0.020(3) -0.005(2) 0.005(2) -0.001(2)
C38 0.030(3) 0.015(3) 0.022(3) 0.003(2) 0.006(3) 0.003(2)
C39 0.038(4) 0.035(4) 0.037(4) 0.003(3) 0.017(3) 0.008(3)
C40 0.041(4) 0.023(3) 0.030(3) 0.001(3) 0.001(3) 0.001(3)
C41 0.024(3) 0.023(3) 0.018(3) -0.001(2) 0.003(2) 0.002(2)
C42 0.030(3) 0.021(3) 0.018(3) 0.001(2) 0.006(2) -0.010(2)
C43 0.034(3) 0.024(3) 0.023(3) 0.001(3) 0.010(3) 0.009(3)
C44 0.036(3) 0.025(3) 0.019(3) 0.005(3) 0.005(3) -0.003(3)
C45 0.044(4) 0.022(3) 0.028(3) 0.006(3) 0.002(3) -0.001(3)
C46 0.071(5) 0.027(4) 0.045(4) 0.016(3) 0.017(3) 0.004(3)
C47 0.090(6) 0.040(4) 0.055(5) 0.025(4) 0.018(4) 0.007(4)
C48 0.063(5) 0.018(3) 0.068(5) 0.005(4) -0.029(4) 0.001(3)
C49 0.051(4) 0.037(4) 0.056(4) -0.005(4) 0.007(3) 0.002(3)
C50 0.057(4) 0.023(4) 0.036(4) 0.006(3) 0.010(3) 0.007(3)
C51 0.024(3) 0.037(4) 0.030(3) 0.005(3) -0.002(3) 0.007(3)
C52 0.020(3) 0.029(3) 0.025(3) 0.005(3) 0.008(2) 0.002(3)
C53 0.035(3) 0.027(3) 0.021(3) 0.004(3) 0.001(3) 0.003(3)
C54 0.047(4) 0.031(4) 0.022(3) 0.003(3) 0.000(3) -0.006(3)
C55 0.076(5) 0.032(4) 0.034(4) 0.010(3) -0.003(3) -0.017(3)
C56 0.085(5) 0.018(3) 0.050(5) 0.004(3) -0.007(4) -0.012(3)
C57 0.100(6) 0.028(4) 0.031(4) 0.005(3) -0.003(4) 0.004(4)
C58 0.063(4) 0.034(4) 0.028(4) 0.000(3) 0.013(3) 0.000(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 O2 C14 116.2(4)
C23 O4 C9 118.5(4)
C7 N1 C10 117.2(4)
C7 N1 C8 120.8(4)
C10 N1 C8 120.9(4)
O1 C1 C2 113.5(4)
O1 C1 C9 113.0(4)
C2 C1 C9 107.2(4)
O1 C1 C12 109.2(4)
C2 C1 C12 111.2(4)
C9 C1 C12 102.1(4)
C3 C2 C7 119.3(5)
C3 C2 C1 122.2(5)
C7 C2 C1 118.6(5)
C2 C3 C4 121.5(5)
C5 C4 C3 120.3(5)
C4 C5 C6 118.7(5)
C7 C6 C5 121.8(5)
N1 C7 C6 122.3(5)
N1 C7 C2 119.1(4)
C6 C7 C2 118.5(5)
N1 C8 C22 112.2(4)
N1 C8 C9 107.9(4)
C22 C8 C9 110.6(4)
N1 C8 C13 113.3(4)
C22 C8 C13 112.9(4)
C9 C8 C13 99.1(4)
O4 C9 C1 111.6(4)
O4 C9 C8 112.6(4)
C1 C9 C8 101.9(4)
C11 C12 C1 114.4(4)
C11 C12 C13 111.3(4)
C1 C12 C13 103.8(4)
C14 C13 C8 112.9(4)
C14 C13 C12 113.2(4)
C8 C13 C12 106.3(4)
O2 C14 C13 105.5(4)
O3 C15 O2 123.6(5)
O3 C15 C16 123.2(5)
O2 C15 C16 113.3(5)
C21 C16 C17 118.4(5)
C21 C16 C15 123.0(5)
C17 C16 C15 118.6(5)
C18 C17 C16 121.7(6)
C19 C18 C17 117.6(6)
C20 C19 C18 122.6(6)
C20 C19 Br1 119.2(5)
C18 C19 Br1 118.2(5)
C19 C20 C21 119.2(6)
C20 C21 C16 120.4(5)
O5 C23 O4 123.4(5)
O5 C23 C24 124.2(5)
O4 C23 C24 112.4(4)
C25 C24 C29 118.3(5)
C25 C24 C23 118.6(5)
C29 C24 C23 123.0(5)
C26 C25 C24 120.1(6)
C27 C26 C25 119.3(6)
C26 C27 C28 122.5(6)
C26 C27 Br2 119.0(5)
C28 C27 Br2 118.5(5)
C29 C28 C27 118.6(6)
C28 C29 C24 121.2(6)
C52 O7 C38 117.2(4)
C44 O9 C43 116.1(4)
C36 N2 C37 120.7(4)
C36 N2 C39 118.0(4)
C37 N2 C39 120.6(4)
O6 C30 C31 111.5(4)
O6 C30 C38 113.0(4)
C31 C30 C38 108.4(4)
O6 C30 C41 109.4(4)
C31 C30 C41 111.9(4)
C38 C30 C41 102.3(4)
C32 C31 C36 118.8(5)
C32 C31 C30 123.6(5)
C36 C31 C30 117.6(5)
C33 C32 C31 121.2(5)
C32 C33 C34 120.8(5)
C33 C34 C35 119.7(5)
C36 C35 C34 120.5(5)
N2 C36 C35 121.8(5)
N2 C36 C31 119.3(4)
C35 C36 C31 118.9(5)
N2 C37 C51 112.9(4)
N2 C37 C38 108.9(4)
C51 C37 C38 110.4(4)
N2 C37 C42 112.0(4)
C51 C37 C42 113.1(4)
C38 C37 C42 98.6(4)
O7 C38 C30 112.0(4)
O7 C38 C37 110.5(4)
C30 C38 C37 101.2(4)
C40 C41 C30 114.3(4)
C40 C41 C42 112.6(4)
C30 C41 C42 103.6(4)
C43 C42 C41 114.3(4)
C43 C42 C37 112.7(4)
C41 C42 C37 106.7(4)
O9 C43 C42 105.8(4)
O10 C44 O9 123.8(5)
O10 C44 C45 123.7(5)
O9 C44 C45 112.5(5)
C50 C45 C46 119.1(5)
C50 C45 C44 123.3(5)
C46 C45 C44 117.6(5)
C47 C46 C45 121.3(6)
C46 C47 C48 118.3(6)
C49 C48 C47 122.2(6)
C49 C48 Br3 119.0(6)
C47 C48 Br3 118.8(5)
C48 C49 C50 118.0(6)
C45 C50 C49 121.1(5)
O8 C52 O7 124.1(5)
O8 C52 C53 124.9(5)
O7 C52 C53 111.0(5)
C58 C53 C54 119.5(5)
C58 C53 C52 122.6(5)
C54 C53 C52 117.8(5)
C55 C54 C53 120.3(5)
C56 C55 C54 118.9(5)
C55 C56 C57 122.0(6)
C55 C56 Br4 119.6(5)
C57 C56 Br4 118.4(5)
C56 C57 C58 119.5(6)
C53 C58 C57 119.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C19 1.893(6)
Br2 C27 1.913(6)
O1 C1 1.421(5)
O2 C15 1.322(6)
O2 C14 1.461(6)
O3 C15 1.213(6)
O4 C23 1.339(6)
O4 C9 1.435(6)
O5 C23 1.206(6)
N1 C7 1.381(6)
N1 C10 1.457(6)
N1 C8 1.452(6)
C1 C2 1.496(7)
C1 C9 1.518(7)
C1 C12 1.543(7)
C2 C3 1.380(7)
C2 C7 1.411(7)
C3 C4 1.378(7)
C4 C5 1.382(8)
C5 C6 1.396(8)
C6 C7 1.387(7)
C8 C22 1.530(7)
C8 C9 1.535(7)
C8 C13 1.540(7)
C11 C12 1.522(7)
C12 C13 1.566(7)
C13 C14 1.504(6)
C15 C16 1.467(7)
C16 C21 1.387(7)
C16 C17 1.395(7)
C17 C18 1.372(8)
C18 C19 1.377(8)
C19 C20 1.364(8)
C20 C21 1.377(8)
C23 C24 1.457(7)
C24 C25 1.391(7)
C24 C29 1.393(8)
C25 C26 1.372(8)
C26 C27 1.354(9)
C27 C28 1.361(8)
C28 C29 1.358(8)
Br3 C48 1.900(6)
Br4 C56 1.899(6)
O6 C30 1.430(6)
O7 C52 1.348(6)
O7 C38 1.438(5)
O8 C52 1.197(6)
O9 C44 1.331(6)
O9 C43 1.464(6)
O10 C44 1.200(6)
N2 C36 1.380(6)
N2 C37 1.453(6)
N2 C39 1.461(6)
C30 C31 1.499(7)
C30 C38 1.513(7)
C30 C41 1.535(7)
C31 C32 1.388(7)
C31 C36 1.422(7)
C32 C33 1.358(7)
C33 C34 1.372(7)
C34 C35 1.394(8)
C35 C36 1.386(7)
C37 C51 1.531(7)
C37 C38 1.539(7)
C37 C42 1.553(7)
C40 C41 1.514(7)
C41 C42 1.548(7)
C42 C43 1.494(6)
C44 C45 1.470(7)
C45 C50 1.381(7)
C45 C46 1.381(7)
C46 C47 1.360(8)
C47 C48 1.390(9)
C48 C49 1.369(9)
C49 C50 1.381(8)
C52 C53 1.479(7)
C53 C58 1.365(7)
C53 C54 1.397(7)
C54 C55 1.373(7)
C55 C56 1.356(8)
C56 C57 1.362(8)
C57 C58 1.386(8)
|
1501999.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501999.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1501999
loop_
_publ_author_name
'Zhang, Shaoguang'
'Zhao, Jing'
'Zhang, Wen-Xiong'
'Xi, Zhenfeng'
_publ_section_title
;
One-pot synthesis of pyrrolo[3,2-d]pyridazines and pyrrole-2,3-diones via
zirconocene-mediated four-component coupling of Si-tethered diyne,
nitriles, and azide.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1626
_journal_page_last 1629
_journal_paper_doi 10.1021/ol200038n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C31 H34 N4 O'
_chemical_formula_weight 478.62
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 84.00(3)
_cell_angle_beta 69.82(3)
_cell_angle_gamma 79.15(3)
_cell_formula_units_Z 2
_cell_length_a 10.912(2)
_cell_length_b 11.048(2)
_cell_length_c 12.028(2)
_cell_measurement_reflns_used 8789
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 2.21
_cell_volume 1335.5(5)
_computing_cell_refinement Rapid-AUTO
_computing_data_collection 'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement SHELXL-97,(Sheldrick,1997)
_computing_structure_solution SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method \W
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0466
_diffrn_reflns_av_sigmaI/netI 0.1263
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 8789
_diffrn_reflns_theta_full 27.48
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_min 2.21
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.073
_exptl_absorpt_correction_T_max 0.9855
_exptl_absorpt_correction_T_min 0.9784
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.190
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description column
_exptl_crystal_F_000 512
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.222
_refine_diff_density_min -0.189
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef 0.0282(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.003
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 342
_refine_ls_number_reflns 5840
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.002
_refine_ls_R_factor_all 0.1330
_refine_ls_R_factor_gt 0.0489
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0905
_refine_ls_wR_factor_ref 0.0976
_reflns_number_gt 2325
_reflns_number_total 5840
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200038n_si_002.cif
_cod_data_source_block zsg14
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1335.4(5)
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1501999
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N2 N 0.22163(16) 0.64692(14) 0.07229(15) 0.0429(5) Uani 1 1 d .
N3 N 0.28085(16) 0.56133(15) 0.13425(14) 0.0448(5) Uani 1 1 d .
N1 N 0.37720(15) 0.32211(14) -0.08402(15) 0.0416(5) Uani 1 1 d .
N4 N 0.17122(19) 0.76407(14) 0.12681(15) 0.0444(5) Uani 1 1 d D
C5 C 0.33107(19) 0.45108(18) 0.08905(17) 0.0382(5) Uani 1 1 d .
C4 C 0.20014(19) 0.63416(17) -0.03141(17) 0.0371(5) Uani 1 1 d .
C6 C 0.32278(19) 0.42561(17) -0.02056(18) 0.0370(5) Uani 1 1 d .
C3 C 0.25120(18) 0.51645(17) -0.07839(17) 0.0362(5) Uani 1 1 d .
C2 C 0.25923(19) 0.46142(17) -0.18467(17) 0.0367(5) Uani 1 1 d .
C28 C 0.0564(2) 0.53834(18) -0.24007(19) 0.0448(6) Uani 1 1 d .
H28 H 0.0056 0.5312 -0.1605 0.054 Uiso 1 1 calc R
C29 C 0.1309(2) 0.73992(17) -0.08812(17) 0.0411(5) Uani 1 1 d .
H29 H 0.1356 0.7108 -0.1639 0.049 Uiso 1 1 d R
C14 C 0.38151(19) 0.35947(19) 0.16913(18) 0.0416(6) Uani 1 1 d .
C23 C 0.1929(2) 0.50736(17) -0.27317(18) 0.0385(5) Uani 1 1 d .
C25 C 0.2009(3) 0.5576(2) -0.4773(2) 0.0586(6) Uani 1 1 d .
H25 H 0.2503 0.5627 -0.5575 0.070 Uiso 1 1 calc R
C8 C 0.0196(2) 0.87016(19) 0.30398(19) 0.0471(6) Uani 1 1 d .
C24 C 0.2641(2) 0.51668(18) -0.39432(19) 0.0497(6) Uani 1 1 d .
H24 H 0.3558 0.4951 -0.4201 0.060 Uiso 1 1 calc R
C19 C 0.3563(2) 0.23951(19) 0.18235(19) 0.0495(6) Uani 1 1 d .
H19 H 0.3163 0.2133 0.1343 0.059 Uiso 1 1 calc R
C30 C 0.1966(2) 0.85599(18) -0.11893(19) 0.0582(7) Uani 1 1 d .
H30A H 0.1734 0.9015 -0.0488 0.087 Uiso 1 1 calc R
H30B H 0.1666 0.9067 -0.1773 0.087 Uiso 1 1 calc R
H30C H 0.2910 0.8323 -0.1499 0.087 Uiso 1 1 calc R
C1 C 0.33719(19) 0.34670(18) -0.18316(18) 0.0396(5) Uani 1 1 d .
C9 C 0.0827(2) 0.9715(2) 0.2814(2) 0.0644(7) Uani 1 1 d .
H9 H 0.1699 0.9659 0.2308 0.077 Uiso 1 1 calc R
C26 C 0.0665(3) 0.59023(19) -0.4410(2) 0.0562(7) Uani 1 1 d .
H26 H 0.0243 0.6194 -0.4960 0.067 Uiso 1 1 calc R
C20 C 0.3805(2) 0.24974(18) -0.27506(19) 0.0475(6) Uani 1 1 d .
H20 H 0.3318 0.2763 -0.3306 0.057 Uiso 1 1 d R
C31 C -0.0163(2) 0.7706(2) -0.0172(2) 0.0633(7) Uani 1 1 d .
H31A H -0.0542 0.6962 0.0017 0.095 Uiso 1 1 calc R
H31B H -0.0601 0.8266 -0.0634 0.095 Uiso 1 1 calc R
H31C H -0.0271 0.8081 0.0548 0.095 Uiso 1 1 calc R
C15 C 0.4442(2) 0.3957(2) 0.24061(19) 0.0510(6) Uani 1 1 d .
H15 H 0.4629 0.4756 0.2321 0.061 Uiso 1 1 calc R
C27 C -0.0062(2) 0.57981(19) -0.3229(2) 0.0533(6) Uani 1 1 d .
H27 H -0.0979 0.6006 -0.2982 0.064 Uiso 1 1 calc R
C13 C -0.1081(2) 0.8801(2) 0.3800(2) 0.0603(7) Uani 1 1 d .
H13 H -0.1514 0.8121 0.3966 0.072 Uiso 1 1 calc R
C21 C 0.3463(2) 0.12395(18) -0.2202(2) 0.0655(7) Uani 1 1 d .
H21A H 0.3895 0.0970 -0.1625 0.098 Uiso 1 1 calc R
H21B H 0.3758 0.0652 -0.2813 0.098 Uiso 1 1 calc R
H21C H 0.2523 0.1307 -0.1825 0.098 Uiso 1 1 calc R
C22 C 0.5280(2) 0.2404(2) -0.3452(2) 0.0722(8) Uani 1 1 d .
H22A H 0.5463 0.3195 -0.3818 0.108 Uiso 1 1 calc R
H22B H 0.5524 0.1812 -0.4052 0.108 Uiso 1 1 calc R
H22C H 0.5780 0.2147 -0.2926 0.108 Uiso 1 1 calc R
C18 C 0.3905(2) 0.1585(2) 0.2669(2) 0.0597(7) Uani 1 1 d .
H18 H 0.3717 0.0787 0.2761 0.072 Uiso 1 1 calc R
C7 C 0.0890(2) 0.74666(19) 0.2509(2) 0.0678(8) Uani 1 1 d .
H7A H 0.1440 0.7041 0.2960 0.081 Uiso 1 1 calc R
H7B H 0.0237 0.6960 0.2554 0.081 Uiso 1 1 calc R
C11 C -0.1106(3) 1.0915(2) 0.4092(2) 0.0701(8) Uani 1 1 d .
H11 H -0.1544 1.1657 0.4444 0.084 Uiso 1 1 calc R
C10 C 0.0163(3) 1.0819(2) 0.3339(2) 0.0711(8) Uani 1 1 d .
H10 H 0.0592 1.1501 0.3175 0.085 Uiso 1 1 calc R
C17 C 0.4523(2) 0.1951(2) 0.3377(2) 0.0664(7) Uani 1 1 d .
H17 H 0.4757 0.1401 0.3938 0.080 Uiso 1 1 calc R
C16 C 0.4787(2) 0.3136(2) 0.3241(2) 0.0614(7) Uani 1 1 d .
H16 H 0.5201 0.3389 0.3715 0.074 Uiso 1 1 calc R
C12 C -0.1734(3) 0.9908(2) 0.4326(2) 0.0720(8) Uani 1 1 d .
H12 H -0.2602 0.9966 0.4840 0.086 Uiso 1 1 calc R
O1 O 0.58069(18) 0.12438(19) 0.93351(18) 0.0795(5) Uani 1 1 d D
H4 H 0.2496(13) 0.795(2) 0.122(2) 0.096(9) Uiso 1 1 d D
H1A H 0.5070(17) 0.1875(17) 0.934(2) 0.127(12) Uiso 1 1 d D
H1B H 0.561(4) 0.060(3) 0.994(2) 0.22(2) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0547(12) 0.0316(10) 0.0383(11) -0.0088(9) -0.0100(10) -0.0035(9)
N3 0.0541(12) 0.0384(11) 0.0372(11) -0.0044(9) -0.0111(10) -0.0027(9)
N1 0.0437(11) 0.0327(10) 0.0425(11) -0.0099(9) -0.0071(9) -0.0012(8)
N4 0.0593(14) 0.0312(10) 0.0362(12) -0.0136(9) -0.0068(11) -0.0024(10)
C5 0.0399(13) 0.0346(12) 0.0344(13) -0.0010(11) -0.0051(11) -0.0068(10)
C4 0.0392(13) 0.0363(12) 0.0306(12) -0.0016(10) -0.0041(11) -0.0079(10)
C6 0.0362(13) 0.0321(12) 0.0377(13) -0.0032(11) -0.0051(11) -0.0067(10)
C3 0.0373(13) 0.0321(12) 0.0331(13) -0.0056(10) -0.0021(11) -0.0068(10)
C2 0.0407(13) 0.0305(12) 0.0344(13) -0.0055(10) -0.0050(11) -0.0069(10)
C28 0.0453(15) 0.0446(13) 0.0403(14) -0.0042(11) -0.0069(12) -0.0097(11)
C29 0.0502(15) 0.0333(12) 0.0357(13) -0.0027(10) -0.0088(12) -0.0067(11)
C14 0.0407(13) 0.0416(14) 0.0368(13) -0.0101(11) -0.0058(11) -0.0016(11)
C23 0.0456(14) 0.0309(12) 0.0347(13) -0.0075(10) -0.0054(12) -0.0081(10)
C25 0.0721(19) 0.0651(17) 0.0348(14) -0.0057(12) -0.0118(14) -0.0116(14)
C8 0.0641(17) 0.0392(13) 0.0319(13) -0.0099(11) -0.0094(13) -0.0018(13)
C24 0.0492(15) 0.0531(15) 0.0419(15) -0.0100(12) -0.0079(13) -0.0056(12)
C19 0.0525(15) 0.0467(15) 0.0482(15) -0.0031(12) -0.0156(13) -0.0069(12)
C30 0.0829(18) 0.0404(13) 0.0476(15) 0.0019(12) -0.0149(14) -0.0157(13)
C1 0.0413(13) 0.0371(13) 0.0376(13) -0.0097(11) -0.0052(11) -0.0099(10)
C9 0.0719(18) 0.0450(15) 0.0619(18) -0.0165(14) -0.0015(14) -0.0070(14)
C26 0.0710(19) 0.0542(16) 0.0508(18) -0.0029(13) -0.0280(16) -0.0129(14)
C20 0.0509(15) 0.0402(13) 0.0473(15) -0.0171(11) -0.0096(12) -0.0024(11)
C31 0.0577(17) 0.0594(16) 0.0648(17) -0.0104(13) -0.0160(14) 0.0053(13)
C15 0.0547(15) 0.0482(14) 0.0443(15) -0.0071(12) -0.0099(13) -0.0044(12)
C27 0.0480(15) 0.0537(15) 0.0597(17) -0.0089(13) -0.0163(15) -0.0113(12)
C13 0.0670(18) 0.0557(16) 0.0543(17) -0.0142(13) -0.0111(15) -0.0118(14)
C21 0.0712(18) 0.0461(14) 0.0768(19) -0.0201(14) -0.0174(15) -0.0083(13)
C22 0.0614(18) 0.0809(18) 0.0594(17) -0.0299(14) 0.0030(14) -0.0052(14)
C18 0.0653(17) 0.0433(14) 0.0622(17) 0.0053(13) -0.0150(15) -0.0055(12)
C7 0.099(2) 0.0422(14) 0.0407(15) -0.0104(12) 0.0039(14) -0.0081(14)
C11 0.085(2) 0.0524(17) 0.0620(19) -0.0249(15) -0.0139(17) 0.0077(16)
C10 0.085(2) 0.0484(16) 0.078(2) -0.0225(15) -0.0185(17) -0.0097(15)
C17 0.0754(19) 0.0673(18) 0.0538(17) 0.0012(15) -0.0251(15) -0.0008(15)
C16 0.0683(18) 0.0648(18) 0.0541(17) -0.0085(15) -0.0248(14) -0.0066(14)
C12 0.0652(18) 0.0684(18) 0.0620(19) -0.0184(15) 0.0050(14) -0.0029(16)
O1 0.0637(13) 0.0785(14) 0.0877(15) -0.0152(12) -0.0226(11) 0.0100(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 N2 C4 128.36(16)
N3 N2 N4 114.17(15)
C4 N2 N4 117.43(17)
C5 N3 N2 117.74(16)
C6 N1 C1 103.93(16)
N2 N4 C7 110.17(16)
N2 N4 H4 103.6(14)
C7 N4 H4 110.6(15)
N3 C5 C6 120.56(18)
N3 C5 C14 113.74(18)
C6 C5 C14 125.42(17)
N2 C4 C3 113.93(18)
N2 C4 C29 121.26(17)
C3 C4 C29 124.79(18)
N1 C6 C5 128.42(19)
N1 C6 C3 112.18(17)
C5 C6 C3 119.39(17)
C4 C3 C6 119.74(18)
C4 C3 C2 134.52(19)
C6 C3 C2 105.52(16)
C1 C2 C3 104.38(16)
C1 C2 C23 125.64(17)
C3 C2 C23 129.80(17)
C23 C28 C27 121.6(2)
C23 C28 H28 119.2
C27 C28 H28 119.2
C4 C29 C31 112.06(18)
C4 C29 C30 114.98(17)
C31 C29 C30 111.47(17)
C4 C29 H29 105.8
C31 C29 H29 105.9
C30 C29 H29 105.8
C19 C14 C15 118.7(2)
C19 C14 C5 120.56(19)
C15 C14 C5 120.43(19)
C28 C23 C24 116.8(2)
C28 C23 C2 121.39(19)
C24 C23 C2 121.76(19)
C26 C25 C24 120.0(2)
C26 C25 H25 120.0
C24 C25 H25 120.0
C13 C8 C9 118.9(2)
C13 C8 C7 119.0(2)
C9 C8 C7 122.0(2)
C25 C24 C23 121.5(2)
C25 C24 H24 119.3
C23 C24 H24 119.3
C18 C19 C14 120.2(2)
C18 C19 H19 119.9
C14 C19 H19 119.9
C29 C30 H30A 109.5
C29 C30 H30B 109.5
H30A C30 H30B 109.5
C29 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
C2 C1 N1 113.94(16)
C2 C1 C20 127.45(18)
N1 C1 C20 118.60(17)
C8 C9 C10 120.1(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C25 C26 C27 119.8(2)
C25 C26 H26 120.1
C27 C26 H26 120.1
C1 C20 C22 110.92(17)
C1 C20 C21 112.13(18)
C22 C20 C21 111.00(18)
C1 C20 H20 107.3
C22 C20 H20 107.8
C21 C20 H20 107.5
C29 C31 H31A 109.5
C29 C31 H31B 109.5
H31A C31 H31B 109.5
C29 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C16 C15 C14 120.4(2)
C16 C15 H15 119.8
C14 C15 H15 119.8
C26 C27 C28 120.4(2)
C26 C27 H27 119.8
C28 C27 H27 119.8
C8 C13 C12 120.5(2)
C8 C13 H13 119.7
C12 C13 H13 119.7
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C20 C22 H22A 109.5
C20 C22 H22B 109.5
H22A C22 H22B 109.5
C20 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C17 C18 C19 120.8(2)
C17 C18 H18 119.6
C19 C18 H18 119.6
N4 C7 C8 110.51(18)
N4 C7 H7A 109.5
C8 C7 H7A 109.5
N4 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C10 C11 C12 119.3(2)
C10 C11 H11 120.4
C12 C11 H11 120.4
C11 C10 C9 120.8(2)
C11 C10 H10 119.6
C9 C10 H10 119.6
C16 C17 C18 119.2(2)
C16 C17 H17 120.4
C18 C17 H17 120.4
C17 C16 C15 120.6(2)
C17 C16 H16 119.7
C15 C16 H16 119.7
C11 C12 C13 120.3(2)
C11 C12 H12 119.8
C13 C12 H12 119.8
H1A O1 H1B 115(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 N3 1.350(2)
N2 C4 1.372(2)
N2 N4 1.438(2)
N3 C5 1.327(2)
N1 C6 1.363(2)
N1 C1 1.390(2)
N4 C7 1.466(3)
N4 H4 0.9602(11)
C5 C6 1.412(2)
C5 C14 1.486(3)
C4 C3 1.409(2)
C4 C29 1.503(2)
C6 C3 1.427(3)
C3 C2 1.441(2)
C2 C1 1.389(2)
C2 C23 1.482(3)
C28 C23 1.386(3)
C28 C27 1.388(3)
C28 H28 0.9300
C29 C31 1.527(3)
C29 C30 1.536(3)
C29 H29 0.9800
C14 C19 1.386(3)
C14 C15 1.396(3)
C23 C24 1.398(3)
C25 C26 1.366(3)
C25 C24 1.393(3)
C25 H25 0.9300
C8 C13 1.368(3)
C8 C9 1.378(3)
C8 C7 1.518(3)
C24 H24 0.9300
C19 C18 1.385(3)
C19 H19 0.9300
C30 H30A 0.9600
C30 H30B 0.9600
C30 H30C 0.9600
C1 C20 1.513(2)
C9 C10 1.387(3)
C9 H9 0.9300
C26 C27 1.372(3)
C26 H26 0.9300
C20 C22 1.527(3)
C20 C21 1.529(3)
C20 H20 0.9800
C31 H31A 0.9600
C31 H31B 0.9600
C31 H31C 0.9600
C15 C16 1.384(3)
C15 H15 0.9300
C27 H27 0.9300
C13 C12 1.388(3)
C13 H13 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C18 C17 1.383(3)
C18 H18 0.9300
C7 H7A 0.9700
C7 H7B 0.9700
C11 C10 1.360(3)
C11 C12 1.369(3)
C11 H11 0.9300
C10 H10 0.9300
C17 C16 1.374(3)
C17 H17 0.9300
C16 H16 0.9300
C12 H12 0.9300
O1 H1A 0.9598(11)
O1 H1B 0.9598(11)
|
1502000.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502000.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502000
loop_
_publ_author_name
'Zhang, Shaoguang'
'Zhao, Jing'
'Zhang, Wen-Xiong'
'Xi, Zhenfeng'
_publ_section_title
;
One-pot synthesis of pyrrolo[3,2-d]pyridazines and pyrrole-2,3-diones via
zirconocene-mediated four-component coupling of Si-tethered diyne,
nitriles, and azide.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1626
_journal_page_last 1629
_journal_paper_doi 10.1021/ol200038n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C24 H25 N O2'
_chemical_formula_weight 359.45
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 82.83(3)
_cell_angle_beta 80.74(3)
_cell_angle_gamma 82.40(3)
_cell_formula_units_Z 2
_cell_length_a 6.2237(12)
_cell_length_b 12.171(2)
_cell_length_c 13.138(3)
_cell_measurement_reflns_used 5883
_cell_measurement_temperature 153(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 2.44
_cell_volume 968.1(3)
_computing_cell_refinement Rapid-AUTO
_computing_data_collection 'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement SHELXL-97,(Sheldrick,1997)
_computing_structure_solution SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature 153(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method \W
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0605
_diffrn_reflns_av_sigmaI/netI 0.1327
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 5883
_diffrn_reflns_theta_full 27.48
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_min 2.44
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_T_max 0.9771
_exptl_absorpt_correction_T_min 0.9696
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_density_diffrn 1.233
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 384
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.30
_refine_diff_density_max 0.233
_refine_diff_density_min -0.238
_refine_diff_density_rms 0.060
_refine_ls_extinction_coef 0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.001
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 253
_refine_ls_number_reflns 4104
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.001
_refine_ls_R_factor_all 0.1245
_refine_ls_R_factor_gt 0.0518
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1064
_refine_ls_wR_factor_ref 0.1209
_reflns_number_gt 1936
_reflns_number_total 4104
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200038n_si_003.cif
_cod_data_source_block zsg17a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502000
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7714(3) 0.6227(2) 0.85850(17) 0.0234(6) Uani 1 1 d .
C2 C 0.8302(3) 0.70640(19) 0.78077(17) 0.0216(6) Uani 1 1 d .
C3 C 0.6878(3) 0.8035(2) 0.80106(17) 0.0238(6) Uani 1 1 d .
C4 C 0.5466(3) 0.7763(2) 0.89066(18) 0.0236(6) Uani 1 1 d .
C5 C 0.8438(4) 0.5069(2) 0.87957(18) 0.0266(6) Uani 1 1 d .
C6 C 1.0498(4) 0.4579(2) 0.82350(18) 0.0259(6) Uani 1 1 d .
C7 C 1.0559(4) 0.3545(2) 0.79089(18) 0.0297(6) Uani 1 1 d .
H7 H 0.9283 0.3169 0.8053 0.036 Uiso 1 1 calc R
C8 C 1.2430(4) 0.3052(2) 0.73802(19) 0.0399(7) Uani 1 1 d .
H8 H 1.2451 0.2339 0.7152 0.048 Uiso 1 1 calc R
C9 C 1.4279(4) 0.3586(2) 0.7179(2) 0.0395(8) Uani 1 1 d .
H9 H 1.5584 0.3244 0.6810 0.047 Uiso 1 1 calc R
C10 C 1.4252(4) 0.4609(2) 0.75063(19) 0.0365(7) Uani 1 1 d .
H10 H 1.5535 0.4980 0.7366 0.044 Uiso 1 1 calc R
C11 C 1.2366(4) 0.5100(2) 0.80380(18) 0.0303(6) Uani 1 1 d .
H11 H 1.2353 0.5808 0.8273 0.036 Uiso 1 1 calc R
C12 C 0.9913(3) 0.70027(19) 0.68496(17) 0.0194(5) Uani 1 1 d .
C13 C 0.9448(3) 0.6329(2) 0.60476(17) 0.0231(6) Uani 1 1 d .
H13 H 0.9168 0.5585 0.6381 0.028 Uiso 1 1 d R
C14 C 0.7405(4) 0.6879(2) 0.5608(2) 0.0381(7) Uani 1 1 d .
H14A H 0.6157 0.6913 0.6167 0.057 Uiso 1 1 calc R
H14B H 0.7103 0.6441 0.5080 0.057 Uiso 1 1 calc R
H14C H 0.7639 0.7635 0.5294 0.057 Uiso 1 1 calc R
C15 C 1.1384(4) 0.6197(2) 0.51956(19) 0.0392(7) Uani 1 1 d .
H15A H 1.1724 0.6934 0.4867 0.059 Uiso 1 1 calc R
H15B H 1.1023 0.5766 0.4676 0.059 Uiso 1 1 calc R
H15C H 1.2657 0.5805 0.5492 0.059 Uiso 1 1 calc R
C16 C 0.6701(4) 0.9087(2) 0.73268(18) 0.0242(6) Uani 1 1 d .
C17 C 0.8381(4) 0.9747(2) 0.7078(2) 0.0335(7) Uani 1 1 d .
H17 H 0.9686 0.9550 0.7379 0.040 Uiso 1 1 calc R
C18 C 0.8172(4) 1.0695(2) 0.6389(2) 0.0420(8) Uani 1 1 d .
H18 H 0.9344 1.1144 0.6224 0.050 Uiso 1 1 calc R
C19 C 0.6316(4) 1.1003(2) 0.5940(2) 0.0350(7) Uani 1 1 d .
H19 H 0.6207 1.1650 0.5457 0.042 Uiso 1 1 calc R
C20 C 0.4636(4) 1.0368(2) 0.61978(19) 0.0317(7) Uani 1 1 d .
H20 H 0.3322 1.0580 0.5906 0.038 Uiso 1 1 calc R
C21 C 0.4827(4) 0.9420(2) 0.68787(18) 0.0275(6) Uani 1 1 d .
H21 H 0.3639 0.8982 0.7046 0.033 Uiso 1 1 calc R
C22 C 0.3722(4) 0.8503(2) 0.94836(18) 0.0297(6) Uani 1 1 d .
H22 H 0.3789 0.9264 0.9144 0.036 Uiso 1 1 d R
C23 C 0.4145(4) 0.8503(2) 1.05913(19) 0.0434(8) Uani 1 1 d .
H23A H 0.4035 0.7757 1.0961 0.065 Uiso 1 1 calc R
H23B H 0.3056 0.9042 1.0943 0.065 Uiso 1 1 calc R
H23C H 0.5617 0.8710 1.0584 0.065 Uiso 1 1 calc R
C24 C 0.1462(4) 0.8187(2) 0.9450(2) 0.0349(7) Uani 1 1 d .
H24A H 0.1248 0.8190 0.8727 0.052 Uiso 1 1 calc R
H24B H 0.0350 0.8726 0.9788 0.052 Uiso 1 1 calc R
H24C H 0.1326 0.7441 0.9814 0.052 Uiso 1 1 calc R
N1 N 0.5994(3) 0.66908(18) 0.92403(15) 0.0258(5) Uani 1 1 d .
O1 O 0.7323(3) 0.44708(14) 0.94267(13) 0.0373(5) Uani 1 1 d .
O2 O 1.1409(2) 0.75608(14) 0.66953(13) 0.0329(5) Uani 1 1 d .
H1 H 0.523(4) 0.629(2) 0.979(2) 0.051(8) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0254(12) 0.0226(15) 0.0212(12) -0.0035(10) 0.0020(10) -0.0052(11)
C2 0.0228(11) 0.0201(14) 0.0213(12) -0.0013(11) 0.0005(10) -0.0059(10)
C3 0.0259(12) 0.0219(14) 0.0226(12) -0.0013(11) 0.0013(10) -0.0058(11)
C4 0.0258(12) 0.0206(15) 0.0250(13) -0.0030(11) -0.0025(10) -0.0062(11)
C5 0.0318(13) 0.0247(15) 0.0224(13) -0.0058(11) 0.0039(11) -0.0069(11)
C6 0.0289(13) 0.0231(15) 0.0220(12) 0.0025(11) 0.0012(11) -0.0009(11)
C7 0.0294(13) 0.0275(16) 0.0304(14) -0.0020(12) 0.0009(11) -0.0044(12)
C8 0.0464(16) 0.0324(17) 0.0347(15) -0.0064(13) 0.0072(13) 0.0041(14)
C9 0.0372(15) 0.038(2) 0.0349(15) -0.0019(14) 0.0062(13) 0.0106(14)
C10 0.0245(13) 0.0430(19) 0.0392(16) 0.0053(14) 0.0000(12) -0.0081(13)
C11 0.0344(14) 0.0263(16) 0.0294(14) 0.0015(12) -0.0052(12) -0.0045(12)
C12 0.0210(11) 0.0107(13) 0.0252(12) 0.0010(10) 0.0000(10) -0.0040(10)
C13 0.0257(12) 0.0225(14) 0.0217(12) -0.0030(10) 0.0022(10) -0.0113(10)
C14 0.0435(15) 0.0394(19) 0.0339(15) -0.0085(13) -0.0116(13) -0.0019(14)
C15 0.0454(15) 0.0383(18) 0.0319(15) -0.0112(13) 0.0138(13) -0.0138(13)
C16 0.0272(12) 0.0189(14) 0.0240(12) -0.0034(10) 0.0046(11) -0.0026(11)
C17 0.0280(13) 0.0295(17) 0.0415(15) 0.0063(13) -0.0039(12) -0.0083(12)
C18 0.0348(14) 0.0285(17) 0.0576(18) 0.0120(14) 0.0016(14) -0.0112(12)
C19 0.0383(14) 0.0200(16) 0.0416(16) 0.0092(12) -0.0015(13) -0.0016(12)
C20 0.0281(13) 0.0287(16) 0.0378(15) 0.0023(13) -0.0071(12) -0.0036(12)
C21 0.0243(12) 0.0249(15) 0.0320(14) -0.0026(12) 0.0028(11) -0.0065(11)
C22 0.0348(13) 0.0235(15) 0.0267(14) -0.0035(11) 0.0078(11) -0.0028(12)
C23 0.0495(17) 0.046(2) 0.0341(16) -0.0180(14) 0.0058(13) -0.0061(14)
C24 0.0304(13) 0.0283(16) 0.0415(16) -0.0054(13) 0.0059(12) 0.0012(12)
N1 0.0303(11) 0.0211(13) 0.0226(11) -0.0011(9) 0.0064(9) -0.0042(9)
O1 0.0408(10) 0.0239(11) 0.0378(10) 0.0046(8) 0.0158(9) -0.0025(8)
O2 0.0326(9) 0.0309(11) 0.0354(10) -0.0064(8) 0.0071(8) -0.0163(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 106.8(2)
N1 C1 C5 118.2(2)
C2 C1 C5 135.0(2)
C1 C2 C3 107.56(19)
C1 C2 C12 129.8(2)
C3 C2 C12 122.27(19)
C4 C3 C2 106.7(2)
C4 C3 C16 126.0(2)
C2 C3 C16 126.71(19)
N1 C4 C3 108.4(2)
N1 C4 C22 123.0(2)
C3 C4 C22 128.5(2)
O1 C5 C1 120.5(2)
O1 C5 C6 119.3(2)
C1 C5 C6 120.2(2)
C11 C6 C7 118.9(2)
C11 C6 C5 122.8(3)
C7 C6 C5 118.3(2)
C8 C7 C6 120.8(3)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 119.8(3)
C7 C8 H8 120.1
C9 C8 H8 120.1
C10 C9 C8 120.2(2)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 119.7(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C10 C11 C6 120.7(3)
C10 C11 H11 119.7
C6 C11 H11 119.7
O2 C12 C2 120.1(2)
O2 C12 C13 122.1(2)
C2 C12 C13 117.35(19)
C12 C13 C15 111.3(2)
C12 C13 C14 109.3(2)
C15 C13 C14 111.0(2)
C12 C13 H13 108.6
C15 C13 H13 108.1
C14 C13 H13 108.4
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 C21 117.7(2)
C17 C16 C3 122.4(2)
C21 C16 C3 119.9(2)
C16 C17 C18 120.0(2)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 121.5(3)
C19 C18 H18 119.2
C17 C18 H18 119.2
C20 C19 C18 118.8(2)
C20 C19 H19 120.6
C18 C19 H19 120.6
C19 C20 C21 120.2(2)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C16 121.7(2)
C20 C21 H21 119.1
C16 C21 H21 119.1
C4 C22 C24 111.6(2)
C4 C22 C23 110.5(2)
C24 C22 C23 111.6(2)
C4 C22 H22 107.7
C24 C22 H22 107.7
C23 C22 H22 107.4
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C22 C24 H24A 109.5
C22 C24 H24B 109.5
H24A C24 H24B 109.5
C22 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C4 N1 C1 110.5(2)
C4 N1 H1 125.8(17)
C1 N1 H1 123.3(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.368(3)
C1 C2 1.390(3)
C1 C5 1.429(3)
C2 C3 1.407(3)
C2 C12 1.481(3)
C3 C4 1.384(3)
C3 C16 1.471(3)
C4 N1 1.340(3)
C4 C22 1.486(3)
C5 O1 1.224(3)
C5 C6 1.465(3)
C6 C11 1.370(3)
C6 C7 1.373(3)
C7 C8 1.363(3)
C7 H7 0.9500
C8 C9 1.369(4)
C8 H8 0.9500
C9 C10 1.364(4)
C9 H9 0.9500
C10 C11 1.370(3)
C10 H10 0.9500
C11 H11 0.9500
C12 O2 1.200(3)
C12 C13 1.497(3)
C13 C15 1.513(3)
C13 C14 1.521(3)
C13 H13 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C17 1.375(3)
C16 C21 1.381(3)
C17 C18 1.379(3)
C17 H17 0.9500
C18 C19 1.368(3)
C18 H18 0.9500
C19 C20 1.357(3)
C19 H19 0.9500
C20 C21 1.373(3)
C20 H20 0.9500
C21 H21 0.9500
C22 C24 1.515(3)
C22 C23 1.520(3)
C22 H22 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
N1 H1 0.92(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 -0.5(3)
C5 C1 C2 C3 177.0(3)
N1 C1 C2 C12 -173.7(2)
C5 C1 C2 C12 3.8(5)
C1 C2 C3 C4 0.1(3)
C12 C2 C3 C4 173.9(2)
C1 C2 C3 C16 -171.6(2)
C12 C2 C3 C16 2.2(4)
C2 C3 C4 N1 0.4(3)
C16 C3 C4 N1 172.2(2)
C2 C3 C4 C22 176.6(2)
C16 C3 C4 C22 -11.6(4)
N1 C1 C5 O1 12.7(4)
C2 C1 C5 O1 -164.6(3)
N1 C1 C5 C6 -169.1(2)
C2 C1 C5 C6 13.6(4)
O1 C5 C6 C11 -139.6(3)
C1 C5 C6 C11 42.2(4)
O1 C5 C6 C7 39.4(4)
C1 C5 C6 C7 -138.9(2)
C11 C6 C7 C8 -1.3(4)
C5 C6 C7 C8 179.7(2)
C6 C7 C8 C9 0.6(4)
C7 C8 C9 C10 0.0(4)
C8 C9 C10 C11 0.0(4)
C9 C10 C11 C6 -0.7(4)
C7 C6 C11 C10 1.3(4)
C5 C6 C11 C10 -179.7(2)
C1 C2 C12 O2 -121.8(3)
C3 C2 C12 O2 65.9(3)
C1 C2 C12 C13 65.0(3)
C3 C2 C12 C13 -107.3(3)
O2 C12 C13 C15 15.7(3)
C2 C12 C13 C15 -171.29(18)
O2 C12 C13 C14 -107.3(2)
C2 C12 C13 C14 65.8(2)
C4 C3 C16 C17 124.4(3)
C2 C3 C16 C17 -65.4(4)
C4 C3 C16 C21 -58.1(4)
C2 C3 C16 C21 112.1(3)
C21 C16 C17 C18 -1.0(4)
C3 C16 C17 C18 176.6(2)
C16 C17 C18 C19 0.0(4)
C17 C18 C19 C20 1.3(4)
C18 C19 C20 C21 -1.5(4)
C19 C20 C21 C16 0.5(4)
C17 C16 C21 C20 0.7(4)
C3 C16 C21 C20 -176.9(2)
N1 C4 C22 C24 -70.2(3)
C3 C4 C22 C24 114.1(3)
N1 C4 C22 C23 54.7(3)
C3 C4 C22 C23 -121.0(3)
C3 C4 N1 C1 -0.7(3)
C22 C4 N1 C1 -177.2(2)
C2 C1 N1 C4 0.8(3)
C5 C1 N1 C4 -177.2(2)
|
1502001.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502001.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502001
loop_
_publ_author_name
'Zhang, Shaoguang'
'Zhao, Jing'
'Zhang, Wen-Xiong'
'Xi, Zhenfeng'
_publ_section_title
;
One-pot synthesis of pyrrolo[3,2-d]pyridazines and pyrrole-2,3-diones via
zirconocene-mediated four-component coupling of Si-tethered diyne,
nitriles, and azide.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1626
_journal_page_last 1629
_journal_paper_doi 10.1021/ol200038n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C24 H24 N2 O'
_chemical_formula_weight 356.45
_chemical_name_systematic
;
?
;
_space_group_IT_number 9
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'C -2yc'
_symmetry_space_group_name_H-M 'C 1 c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 107.72(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.118(2)
_cell_length_b 13.959(3)
_cell_length_c 12.467(3)
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 2.29
_cell_volume 2008.8(8)
_computing_cell_refinement Rapid-AUTO
_computing_data_collection 'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement SHELXL-97,(Sheldrick,1997)
_computing_structure_solution SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method \W
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0685
_diffrn_reflns_av_sigmaI/netI 0.2080
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 3754
_diffrn_reflns_theta_full 27.48
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_min 2.29
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.072
_exptl_absorpt_correction_T_max 0.9857
_exptl_absorpt_correction_T_min 0.9787
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_density_diffrn 1.179
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.215
_refine_diff_density_min -0.218
_refine_diff_density_rms 0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -8(2)
_refine_ls_extinction_coef 0.0092(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 249
_refine_ls_number_reflns 3754
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.022
_refine_ls_R_factor_all 0.1253
_refine_ls_R_factor_gt 0.0539
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0060P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0748
_refine_ls_wR_factor_ref 0.0786
_reflns_number_gt 1427
_reflns_number_total 3754
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200038n_si_004.cif
_cod_data_source_block zsg49a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2008.8(7)
_cod_original_sg_symbol_H-M Cc
_cod_database_code 1502001
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6937(4) 0.7049(3) 0.6225(4) 0.0377(13) Uani 1 1 d .
C2 C 0.7929(3) 0.6846(3) 0.7025(3) 0.0269(12) Uani 1 1 d .
C3 C 0.8873(4) 0.7328(3) 0.6745(4) 0.0315(13) Uani 1 1 d .
C4 C 1.0117(4) 0.7392(3) 0.7269(4) 0.0392(15) Uani 1 1 d .
C5 C 1.0782(4) 0.7903(4) 0.6553(3) 0.0365(14) Uani 1 1 d .
C6 C 0.9038(4) 0.8432(3) 0.5195(4) 0.0383(15) Uani 1 1 d .
C7 C 0.8384(3) 0.7816(3) 0.5739(3) 0.0315(13) Uani 1 1 d .
C8 C 0.5685(4) 0.6787(4) 0.6085(4) 0.0437(15) Uani 1 1 d .
H8 H 0.5689 0.6341 0.6694 0.052 Uiso 1 1 calc R
C9 C 0.4984(4) 0.7666(4) 0.6223(5) 0.089(2) Uani 1 1 d .
H9A H 0.4224 0.7469 0.6218 0.133 Uiso 1 1 calc R
H9B H 0.4922 0.8104 0.5613 0.133 Uiso 1 1 calc R
H9C H 0.5368 0.7977 0.6925 0.133 Uiso 1 1 calc R
C10 C 0.5106(5) 0.6267(5) 0.4969(4) 0.075(2) Uani 1 1 d .
H10A H 0.5603 0.5761 0.4870 0.113 Uiso 1 1 calc R
H10B H 0.4974 0.6713 0.4357 0.113 Uiso 1 1 calc R
H10C H 0.4380 0.6002 0.4983 0.113 Uiso 1 1 calc R
C11 C 0.8059(4) 0.6184(4) 0.8013(4) 0.0346(13) Uani 1 1 d .
C12 C 0.7388(4) 0.6282(4) 0.8721(4) 0.0547(16) Uani 1 1 d .
H12 H 0.6858 0.6783 0.8614 0.066 Uiso 1 1 calc R
C13 C 0.7494(5) 0.5656(5) 0.9570(5) 0.0625(18) Uani 1 1 d .
H13 H 0.7003 0.5716 1.0012 0.075 Uiso 1 1 calc R
C14 C 0.8302(5) 0.4931(5) 0.9808(5) 0.0631(19) Uani 1 1 d .
H14 H 0.8386 0.4526 1.0420 0.076 Uiso 1 1 calc R
C15 C 0.8988(5) 0.4822(4) 0.9106(5) 0.064(2) Uani 1 1 d .
H15 H 0.9522 0.4325 0.9227 0.077 Uiso 1 1 calc R
C16 C 0.8874(4) 0.5462(5) 0.8212(4) 0.0528(17) Uani 1 1 d .
H16 H 0.9349 0.5401 0.7754 0.063 Uiso 1 1 calc R
C17 C 1.1389(4) 0.7093(5) 0.6107(4) 0.0744(19) Uani 1 1 d .
H17A H 1.1803 0.7360 0.5632 0.112 Uiso 1 1 calc R
H17B H 1.0819 0.6647 0.5682 0.112 Uiso 1 1 calc R
H17C H 1.1922 0.6767 0.6730 0.112 Uiso 1 1 calc R
C18 C 1.1682(4) 0.8568(4) 0.7323(4) 0.072(2) Uani 1 1 d .
H18A H 1.1299 0.9107 0.7530 0.108 Uiso 1 1 calc R
H18B H 1.2208 0.8787 0.6935 0.108 Uiso 1 1 calc R
H18C H 1.2106 0.8226 0.7990 0.108 Uiso 1 1 calc R
C19 C 0.8436(4) 0.9044(4) 0.4219(4) 0.0363(13) Uani 1 1 d .
C20 C 0.8987(4) 0.9176(4) 0.3375(4) 0.0503(17) Uani 1 1 d .
H20 H 0.9651 0.8833 0.3397 0.060 Uiso 1 1 calc R
C21 C 0.8528(5) 0.9810(4) 0.2538(4) 0.0582(18) Uani 1 1 d .
H21 H 0.8870 0.9872 0.1968 0.070 Uiso 1 1 calc R
C22 C 0.7572(5) 1.0370(5) 0.2491(4) 0.0630(18) Uani 1 1 d .
H22 H 0.7294 1.0818 0.1921 0.076 Uiso 1 1 calc R
C23 C 0.7047(5) 1.0239(4) 0.3319(5) 0.0601(18) Uani 1 1 d .
H23 H 0.6395 1.0599 0.3300 0.072 Uiso 1 1 calc R
C24 C 0.7476(4) 0.9580(4) 0.4179(4) 0.0446(16) Uani 1 1 d .
H24 H 0.7111 0.9502 0.4731 0.053 Uiso 1 1 calc R
N1 N 0.7201(3) 0.7649(3) 0.5426(3) 0.0336(11) Uani 1 1 d .
H1 H 0.6703 0.7877 0.4833 0.040 Uiso 1 1 calc R
N2 N 1.0154(3) 0.8451(3) 0.5587(3) 0.0398(12) Uani 1 1 d .
O1 O 1.0613(2) 0.7070(2) 0.8210(2) 0.0503(11) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.037(3) 0.042(4) 0.040(3) 0.003(3) 0.019(3) -0.003(3)
C2 0.025(3) 0.020(4) 0.030(3) 0.006(2) 0.001(2) 0.007(2)
C3 0.037(3) 0.033(4) 0.022(3) 0.001(2) 0.004(2) 0.003(2)
C4 0.021(3) 0.052(4) 0.042(3) -0.018(3) 0.006(2) -0.004(2)
C5 0.025(3) 0.047(4) 0.032(3) 0.004(3) 0.000(2) -0.007(3)
C6 0.050(4) 0.044(4) 0.023(3) -0.004(2) 0.014(3) 0.000(3)
C7 0.021(3) 0.037(4) 0.035(3) -0.010(3) 0.006(2) -0.006(3)
C8 0.031(3) 0.055(5) 0.050(3) -0.005(3) 0.020(3) -0.015(3)
C9 0.036(4) 0.098(7) 0.145(6) -0.003(5) 0.046(4) 0.001(4)
C10 0.056(4) 0.091(6) 0.075(5) 0.002(4) 0.011(3) -0.016(3)
C11 0.043(3) 0.032(4) 0.027(3) 0.001(2) 0.009(2) -0.003(3)
C12 0.061(4) 0.062(5) 0.051(4) 0.007(3) 0.032(3) 0.002(3)
C13 0.070(4) 0.076(5) 0.055(4) 0.019(4) 0.038(4) 0.005(4)
C14 0.070(5) 0.069(5) 0.050(4) 0.021(4) 0.019(4) -0.024(4)
C15 0.065(4) 0.064(5) 0.061(4) 0.035(4) 0.015(4) 0.022(3)
C16 0.051(4) 0.067(5) 0.051(4) 0.017(3) 0.031(3) 0.014(3)
C17 0.058(4) 0.096(5) 0.081(4) 0.035(4) 0.038(3) 0.029(4)
C18 0.064(4) 0.084(5) 0.050(4) -0.003(3) -0.010(3) -0.040(3)
C19 0.042(3) 0.036(4) 0.028(3) 0.010(2) 0.007(3) -0.004(3)
C20 0.047(3) 0.065(5) 0.040(3) 0.002(3) 0.015(3) 0.002(3)
C21 0.070(4) 0.075(5) 0.038(4) 0.008(3) 0.028(3) -0.006(4)
C22 0.067(5) 0.070(5) 0.051(4) 0.029(3) 0.016(4) -0.005(4)
C23 0.049(4) 0.075(5) 0.054(4) 0.025(3) 0.012(3) -0.005(3)
C24 0.049(4) 0.057(5) 0.038(3) 0.025(3) 0.029(3) 0.013(3)
N1 0.033(2) 0.041(3) 0.025(2) 0.002(2) 0.0045(18) 0.0038(19)
N2 0.026(2) 0.053(3) 0.042(3) -0.003(2) 0.011(2) -0.013(2)
O1 0.034(2) 0.066(3) 0.041(2) 0.0126(19) -0.0029(17) -0.0006(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 N1 107.9(4)
C2 C1 C8 132.4(4)
N1 C1 C8 119.7(4)
C1 C2 C3 108.4(4)
C1 C2 C11 125.8(4)
C3 C2 C11 125.7(4)
C7 C3 C4 118.3(4)
C7 C3 C2 107.0(4)
C4 C3 C2 134.7(4)
O1 C4 C3 123.1(5)
O1 C4 C5 122.0(4)
C3 C4 C5 114.9(4)
N2 C5 C18 107.4(4)
N2 C5 C17 106.1(4)
C18 C5 C17 110.1(4)
N2 C5 C4 119.6(4)
C18 C5 C4 108.4(4)
C17 C5 C4 105.0(4)
N2 C6 C7 119.2(4)
N2 C6 C19 119.7(4)
C7 C6 C19 121.1(4)
N1 C7 C3 107.0(4)
N1 C7 C6 128.7(4)
C3 C7 C6 124.2(4)
C1 C8 C10 112.5(4)
C1 C8 C9 111.3(4)
C10 C8 C9 111.4(5)
C1 C8 H8 107.1
C10 C8 H8 107.1
C9 C8 H8 107.1
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C16 119.2(5)
C12 C11 C2 121.8(5)
C16 C11 C2 119.0(5)
C13 C12 C11 120.3(6)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 122.5(6)
C14 C13 H13 118.7
C12 C13 H13 118.7
C13 C14 C15 117.9(5)
C13 C14 H14 121.0
C15 C14 H14 121.0
C16 C15 C14 120.0(5)
C16 C15 H15 120.0
C14 C15 H15 120.0
C11 C16 C15 120.0(5)
C11 C16 H16 120.0
C15 C16 H16 120.0
C5 C17 H17A 109.5
C5 C17 H17B 109.5
H17A C17 H17B 109.5
C5 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C5 C18 H18A 109.5
C5 C18 H18B 109.5
H18A C18 H18B 109.5
C5 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C24 C19 C20 119.2(5)
C24 C19 C6 122.9(4)
C20 C19 C6 117.2(4)
C21 C20 C19 118.7(5)
C21 C20 H20 120.6
C19 C20 H20 120.6
C20 C21 C22 123.1(5)
C20 C21 H21 118.5
C22 C21 H21 118.5
C23 C22 C21 117.7(5)
C23 C22 H22 121.2
C21 C22 H22 121.2
C22 C23 C24 121.0(6)
C22 C23 H23 119.5
C24 C23 H23 119.5
C23 C24 C19 120.2(5)
C23 C24 H24 119.9
C19 C24 H24 119.9
C7 N1 C1 109.7(4)
C7 N1 H1 125.1
C1 N1 H1 125.1
C6 N2 C5 122.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.338(5)
C1 N1 1.410(5)
C1 C8 1.519(6)
C2 C3 1.458(6)
C2 C11 1.509(6)
C3 C7 1.391(5)
C3 C4 1.452(5)
C4 O1 1.229(5)
C4 C5 1.547(6)
C5 N2 1.434(5)
C5 C18 1.527(6)
C5 C17 1.542(7)
C6 N2 1.291(5)
C6 C7 1.468(6)
C6 C19 1.484(6)
C7 N1 1.387(5)
C8 C10 1.537(7)
C8 C9 1.531(6)
C8 H8 0.9800
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.377(6)
C11 C16 1.380(7)
C12 C13 1.349(7)
C12 H12 0.9300
C13 C14 1.377(7)
C13 H13 0.9300
C14 C15 1.386(7)
C14 H14 0.9300
C15 C16 1.402(7)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 C24 1.371(6)
C19 C20 1.420(6)
C20 C21 1.352(7)
C20 H20 0.9300
C21 C22 1.383(7)
C21 H21 0.9300
C22 C23 1.380(7)
C22 H22 0.9300
C23 C24 1.389(6)
C23 H23 0.9300
C24 H24 0.9300
N1 H1 0.8600
|
1502002.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502002.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502002
loop_
_publ_author_name
'Abbet, Christian'
'Neuburger, Markus'
'Wagner, Trixie'
'Quitschau, Melanie'
'Hamburger, Matthias'
'Potterat, Olivier'
_publ_section_title
;
Phyteumosides A and B: new saponins with unique triterpenoid aglycons
from Phyteuma orbiculare L.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1354
_journal_page_last 1357
_journal_paper_doi 10.1021/ol200047v
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_moiety 'C32 H52 O6, 2.38(H2 O)'
_chemical_formula_sum 'C32 H56.76 O8.38'
_chemical_formula_weight 571.77
_space_group_IT_number 18
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ac'
_symmetry_space_group_name_H-M 'P 21 2 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 6.4777(15)
_cell_length_b 16.504(5)
_cell_length_c 29.762(7)
_cell_measurement_reflns_used 1279
_cell_measurement_temperature 123
_cell_measurement_theta_max 21
_cell_measurement_theta_min 3
_cell_volume 3181.8(14)
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature 123
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device Area
_diffrn_measurement_device_type 'Bruker Kappa Apex2'
_diffrn_measurement_method '\f & \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.122
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_limit_l_min -38
_diffrn_reflns_number 10935
_diffrn_reflns_theta_full 25.201
_diffrn_reflns_theta_max 27.098
_diffrn_reflns_theta_min 2.395
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.085
_exptl_absorpt_correction_T_max 1.00
_exptl_absorpt_correction_T_min 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.193
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1248
_exptl_crystal_size_max 0.270
_exptl_crystal_size_mid 0.090
_exptl_crystal_size_min 0.010
_refine_diff_density_max 1.02
_refine_diff_density_min -1.12
_refine_ls_extinction_method None
_refine_ls_goodness_of_fit_ref 0.9538
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 373
_refine_ls_number_reflns 3968
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.1551
_refine_ls_R_factor_gt 0.0880
_refine_ls_shift/su_max 0.0041952
_refine_ls_shift/su_mean 0.0004427
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 3.27P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.2294
_refine_ls_wR_factor_gt 0.1988
_refine_ls_wR_factor_ref 0.2294
_reflns_limit_h_max 8
_reflns_limit_h_min 0
_reflns_limit_k_max 21
_reflns_limit_k_min 0
_reflns_limit_l_max 38
_reflns_limit_l_min 0
_reflns_number_gt 2173
_reflns_number_total 3995
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.14
_oxford_diffrn_Wilson_scale 29.24
_oxford_refine_ls_r_factor_ref 0.1551
_oxford_refine_ls_scale 0.1952(3)
_oxford_reflns_number_all 3968
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file ol200047v_si_002.cif
_cod_data_source_block 1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 3181.9(14)
_cod_database_code 1502002
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y,-z+1/2
-x,y,-z
-x+1/2,-y,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.9792(7) 0.7920(3) 0.73033(13) 0.0249 1.0000 Uani . .
C2 C 0.8769(10) 0.8368(4) 0.7662(2) 0.0231 1.0000 Uani . .
C3 C 0.9427(10) 0.7987(4) 0.8112(2) 0.0222 1.0000 Uani . .
C4 C 0.8713(10) 0.7095(4) 0.8122(2) 0.0252 1.0000 Uani . .
C5 C 0.9658(10) 0.6640(4) 0.7721(2) 0.0274 1.0000 Uani . .
C6 C 0.9287(10) 0.7078(4) 0.7279(2) 0.0238 1.0000 Uani . .
C7 C 1.0616(9) 0.6742(4) 0.6889(2) 0.0257 1.0000 Uani . .
O8 O 1.0672(6) 0.5876(3) 0.68958(15) 0.0278 1.0000 Uani . .
C9 C 0.9060(10) 0.5383(4) 0.6684(2) 0.0252 1.0000 Uani . .
C10 C 0.7167(12) 0.5332(4) 0.6997(2) 0.0336 1.0000 Uani . .
C11 C 1.0023(11) 0.4551(4) 0.6645(2) 0.0286 1.0000 Uani . .
C12 C 0.8761(13) 0.3987(4) 0.6350(2) 0.0371 1.0000 Uani . .
C13 C 0.8431(12) 0.4352(5) 0.5881(2) 0.0341 1.0000 Uani . .
O14 O 0.7244(9) 0.3796(3) 0.56043(17) 0.0490 1.0000 Uani . .
C15 C 0.7405(10) 0.5190(4) 0.5876(2) 0.0275 1.0000 Uani . .
C16 C 0.8713(10) 0.5722(4) 0.6211(2) 0.0257 1.0000 Uani . .
C17 C 0.8050(10) 0.6608(4) 0.6245(2) 0.0252 1.0000 Uani . .
C18 C 0.9768(9) 0.7093(4) 0.64364(19) 0.0260 1.0000 Uani . .
O19 O 1.1498(7) 0.7092(3) 0.61125(14) 0.0277 1.0000 Uani . .
C20 C 1.1328(13) 0.7575(5) 0.5754(2) 0.0367 1.0000 Uani . .
O21 O 0.9881(10) 0.8016(3) 0.56976(18) 0.0550 1.0000 Uani . .
C1 C 1.3194(13) 0.7510(5) 0.5460(3) 0.0443 1.0000 Uani . .
C23 C 0.5092(11) 0.5121(5) 0.5995(3) 0.0405 1.0000 Uani . .
C24 C 0.7614(13) 0.5543(5) 0.5409(2) 0.0398 1.0000 Uani . .
C25 C 1.2877(10) 0.6988(5) 0.6951(2) 0.0358 1.0000 Uani . .
C26 C 0.8989(9) 0.8485(4) 0.8546(2) 0.0212 1.0000 Uani . .
C27 C 1.0074(10) 0.9313(4) 0.84752(19) 0.0237 1.0000 Uani . .
C28 C 1.0323(11) 0.9868(4) 0.8895(2) 0.0321 1.0000 Uani . .
C29 C 1.1302(13) 0.9352(5) 0.9266(2) 0.0365 1.0000 Uani . .
O30 O 1.1608(12) 0.9779(3) 0.96809(19) 0.0683 1.0000 Uani . .
C31 C 1.0189(13) 0.8568(4) 0.9363(2) 0.0354 1.0000 Uani . .
C32 C 1.0013(12) 0.8038(4) 0.89426(19) 0.0286 1.0000 Uani . .
C33 C 1.1783(13) 1.0563(5) 0.8787(2) 0.0438 1.0000 Uani . .
C34 C 0.8266(12) 1.0236(5) 0.9056(2) 0.0393 1.0000 Uani . .
C35 C 0.9308(12) 0.9733(4) 0.8051(2) 0.0340 1.0000 Uani . .
C36 C 0.9696(11) 0.9211(4) 0.7623(2) 0.0291 1.0000 Uani . .
C37 C 0.6667(11) 0.8550(5) 0.8642(2) 0.0335 1.0000 Uani . .
C38 C 0.6443(10) 0.8414(4) 0.7570(2) 0.0287 1.0000 Uani . .
O39 O 1.5000 0.8823(5) 1.0000 0.0562 1.0000 Uani S T
O40 O 0.9857(14) 0.2587(5) 0.5545(3) 0.0673 0.7500 Uani . .
O41 O 1.2972(15) 0.3623(5) 0.5338(3) 0.0729 0.7500 Uani . .
H31 H 1.0939 0.7949 0.8100 0.0259 1.0000 Uiso R .
H42 H 0.9109 0.6840 0.8405 0.0265 1.0000 Uiso R .
H41 H 0.7212 0.7087 0.8093 0.0271 1.0000 Uiso R .
H51 H 1.1133 0.6588 0.7766 0.0280 1.0000 Uiso R .
H52 H 0.9045 0.6106 0.7705 0.0277 1.0000 Uiso R .
H61 H 0.7820 0.7034 0.7193 0.0240 1.0000 Uiso R .
H101 H 0.6179 0.4963 0.6870 0.0459 1.0000 Uiso R .
H103 H 0.7572 0.5156 0.7292 0.0458 1.0000 Uiso R .
H102 H 0.6571 0.5865 0.7016 0.0458 1.0000 Uiso R .
H111 H 1.0175 0.4314 0.6942 0.0321 1.0000 Uiso R .
H112 H 1.1382 0.4619 0.6511 0.0319 1.0000 Uiso R .
H122 H 0.7445 0.3887 0.6490 0.0362 1.0000 Uiso R .
H121 H 0.9497 0.3481 0.6324 0.0362 1.0000 Uiso R .
H131 H 0.9789 0.4416 0.5743 0.0430 1.0000 Uiso R .
H161 H 1.0109 0.5731 0.6083 0.0271 1.0000 Uiso R .
H172 H 0.6840 0.6649 0.6438 0.0259 1.0000 Uiso R .
H171 H 0.7717 0.6811 0.5948 0.0257 1.0000 Uiso R .
H181 H 0.9289 0.7649 0.6485 0.0255 1.0000 Uiso R .
H232 H 0.4581 0.5637 0.6086 0.0570 1.0000 Uiso R .
H231 H 0.4892 0.4736 0.6234 0.0570 1.0000 Uiso R .
H233 H 0.4347 0.4943 0.5735 0.0569 1.0000 Uiso R .
H242 H 0.6885 0.6048 0.5395 0.0527 1.0000 Uiso R .
H241 H 0.9042 0.5639 0.5336 0.0529 1.0000 Uiso R .
H243 H 0.7034 0.5179 0.5190 0.0530 1.0000 Uiso R .
H253 H 1.3698 0.6724 0.6725 0.0450 1.0000 Uiso R .
H252 H 1.3344 0.6826 0.7245 0.0449 1.0000 Uiso R .
H251 H 1.3013 0.7563 0.6920 0.0450 1.0000 Uiso R .
H271 H 1.1503 0.9166 0.8406 0.0250 1.0000 Uiso R .
H291 H 1.2678 0.9205 0.9160 0.0441 1.0000 Uiso R .
H312 H 1.0921 0.8274 0.9597 0.0339 1.0000 Uiso R .
H311 H 0.8800 0.8697 0.9465 0.0343 1.0000 Uiso R .
H322 H 1.1406 0.7880 0.8851 0.0340 1.0000 Uiso R .
H321 H 0.9218 0.7560 0.9007 0.0338 1.0000 Uiso R .
H331 H 1.2120 1.0858 0.9054 0.0560 1.0000 Uiso R .
H333 H 1.3022 1.0344 0.8651 0.0560 1.0000 Uiso R .
H332 H 1.1123 1.0918 0.8575 0.0561 1.0000 Uiso R .
H341 H 0.8520 1.0588 0.9306 0.0580 1.0000 Uiso R .
H342 H 0.7353 0.9811 0.9150 0.0580 1.0000 Uiso R .
H343 H 0.7658 1.0539 0.8813 0.0579 1.0000 Uiso R .
H351 H 0.9988 1.0253 0.8021 0.0351 1.0000 Uiso R .
H352 H 0.7830 0.9821 0.8087 0.0349 1.0000 Uiso R .
H362 H 1.1171 0.9152 0.7590 0.0300 1.0000 Uiso R .
H361 H 0.9161 0.9488 0.7361 0.0299 1.0000 Uiso R .
H371 H 0.6478 0.8694 0.8952 0.0488 1.0000 Uiso R .
H373 H 0.6005 0.8041 0.8583 0.0489 1.0000 Uiso R .
H372 H 0.6073 0.8963 0.8458 0.0489 1.0000 Uiso R .
H381 H 0.5838 0.8843 0.7745 0.0409 1.0000 Uiso R .
H383 H 0.6223 0.8523 0.7256 0.0407 1.0000 Uiso R .
H382 H 0.5822 0.7907 0.7649 0.0411 1.0000 Uiso R .
O42 O 1.000000(10) 0.9221(7) 0.500000(10) 0.1342 0.7500 Uani S T
H13 H 1.2902 0.7752 0.5172 0.0573 1.0000 Uiso R .
H12 H 1.4340 0.7787 0.5597 0.0571 1.0000 Uiso R .
H11 H 1.3546 0.6951 0.5418 0.0573 1.0000 Uiso R .
H422 H 0.8970 0.9052 0.5127 0.1849 1.0000 Uiso R .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.026(2) 0.028(3) 0.021(2) 0.0004(19) 0.004(2) -0.002(2)
C2 0.026(3) 0.018(3) 0.026(3) 0.001(3) 0.002(3) 0.003(3)
C3 0.023(3) 0.016(3) 0.028(3) 0.004(3) 0.004(3) 0.004(3)
C4 0.026(3) 0.015(3) 0.034(4) -0.005(3) 0.005(3) 0.003(3)
C5 0.026(4) 0.025(4) 0.032(4) -0.001(3) -0.004(3) 0.003(3)
C6 0.019(3) 0.023(4) 0.030(3) 0.000(3) -0.002(3) 0.001(3)
C7 0.019(3) 0.031(4) 0.027(3) -0.001(3) 0.003(3) 0.004(3)
O8 0.024(2) 0.026(3) 0.033(2) -0.002(2) -0.006(2) 0.008(2)
C9 0.024(3) 0.028(4) 0.024(3) 0.000(3) -0.001(3) -0.009(3)
C10 0.041(4) 0.029(4) 0.031(4) -0.005(3) 0.005(3) 0.003(4)
C11 0.029(4) 0.029(4) 0.028(3) 0.003(3) 0.001(3) 0.005(3)
C12 0.045(4) 0.025(4) 0.042(4) -0.006(3) -0.002(4) -0.004(4)
C13 0.040(4) 0.032(4) 0.030(4) -0.004(3) -0.001(3) -0.003(4)
O14 0.067(4) 0.038(3) 0.042(3) -0.009(3) -0.009(3) -0.015(3)
C15 0.022(3) 0.039(4) 0.022(3) -0.003(3) -0.006(3) -0.008(3)
C16 0.019(3) 0.026(4) 0.032(4) -0.002(3) 0.005(3) 0.001(3)
C17 0.019(3) 0.037(4) 0.020(3) -0.001(3) 0.001(3) 0.000(3)
C18 0.020(3) 0.037(4) 0.022(3) -0.004(3) 0.008(3) -0.004(3)
O19 0.022(2) 0.034(3) 0.027(2) -0.007(2) 0.009(2) -0.004(2)
C20 0.047(5) 0.027(4) 0.036(4) -0.010(3) 0.016(4) -0.002(4)
O21 0.071(4) 0.039(3) 0.055(4) 0.010(3) 0.029(3) 0.015(4)
C1 0.048(5) 0.042(5) 0.043(4) -0.002(4) 0.022(4) 0.003(4)
C23 0.029(4) 0.053(5) 0.040(4) -0.003(4) 0.000(4) -0.007(4)
C24 0.039(4) 0.046(5) 0.034(4) -0.001(4) -0.004(3) -0.006(4)
C25 0.020(3) 0.043(5) 0.044(4) -0.011(4) 0.003(3) -0.007(3)
C26 0.024(3) 0.018(3) 0.022(3) 0.000(3) -0.004(3) -0.001(3)
C27 0.024(3) 0.021(3) 0.026(3) 0.001(3) -0.001(3) -0.005(3)
C28 0.034(4) 0.027(4) 0.036(4) 0.000(3) -0.008(3) -0.008(3)
C29 0.047(4) 0.034(4) 0.029(4) 0.003(3) -0.003(3) -0.009(4)
O30 0.115(6) 0.036(3) 0.054(3) -0.013(3) -0.051(4) 0.008(4)
C31 0.043(4) 0.030(4) 0.033(4) -0.002(3) -0.005(3) -0.003(4)
C32 0.044(4) 0.023(4) 0.019(3) 0.007(3) 0.005(3) 0.000(4)
C33 0.055(5) 0.040(5) 0.036(4) 0.001(4) -0.006(4) -0.022(4)
C34 0.043(5) 0.039(4) 0.036(4) -0.010(3) -0.006(4) 0.006(4)
C35 0.046(4) 0.020(4) 0.036(4) 0.009(3) -0.007(4) -0.006(3)
C36 0.038(4) 0.028(4) 0.022(3) 0.004(3) -0.005(3) -0.008(4)
C37 0.036(4) 0.031(4) 0.034(4) -0.008(3) 0.007(3) -0.008(4)
C38 0.025(3) 0.028(4) 0.033(4) 0.001(3) -0.002(3) 0.009(3)
O39 0.060(5) 0.044(5) 0.064(5) 0.0000 -0.023(5) 0.0000
O40 0.071(6) 0.063(6) 0.068(5) 0.005(4) -0.005(5) 0.031(5)
O41 0.085(7) 0.063(6) 0.071(5) 0.009(5) -0.029(5) -0.026(5)
O42 0.24(2) 0.030(7) 0.136(12) 0.0000 -0.144(15) 0.0000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 C6 115.2(5) yes
O1 . C2 C3 107.8(5) yes
O1 . C2 C36 103.2(5) yes
C3 . C2 C36 109.3(5) yes
O1 . C2 C38 110.0(5) yes
C3 . C2 C38 116.6(5) yes
C36 . C2 C38 109.2(6) yes
C2 . C3 C4 108.8(5) yes
C2 . C3 C26 117.1(5) yes
C4 . C3 C26 115.7(5) yes
C2 . C3 H31 105.5 no
C4 . C3 H31 103.8 no
C26 . C3 H31 104.3 no
C3 . C4 C5 109.4(5) yes
C3 . C4 H42 110.4 no
C5 . C4 H42 110.7 no
C3 . C4 H41 108.1 no
C5 . C4 H41 108.7 no
H42 . C4 H41 109.4 no
C4 . C5 C6 112.2(5) yes
C4 . C5 H51 109.3 no
C6 . C5 H51 108.4 no
C4 . C5 H52 108.8 no
C6 . C5 H52 108.8 no
H51 . C5 H52 109.3 no
C5 . C6 O1 112.4(5) yes
C5 . C6 C7 113.1(5) yes
O1 . C6 C7 105.0(5) yes
C5 . C6 H61 109.9 no
O1 . C6 H61 107.7 no
C7 . C6 H61 108.4 no
C6 . C7 O8 111.2(5) yes
C6 . C7 C18 108.5(5) yes
O8 . C7 C18 113.0(5) yes
C6 . C7 C25 110.3(5) yes
O8 . C7 C25 103.8(5) yes
C18 . C7 C25 110.0(6) yes
C7 . O8 C9 122.0(5) yes
O8 . C9 C10 109.7(5) yes
O8 . C9 C11 104.1(5) yes
C10 . C9 C11 109.0(5) yes
O8 . C9 C16 107.2(5) yes
C10 . C9 C16 117.3(5) yes
C11 . C9 C16 108.7(5) yes
C9 . C10 H101 109.2 no
C9 . C10 H103 110.6 no
H101 . C10 H103 110.4 no
C9 . C10 H102 107.8 no
H101 . C10 H102 109.6 no
H103 . C10 H102 109.3 no
C9 . C11 C12 112.3(6) yes
C9 . C11 H111 109.7 no
C12 . C11 H111 109.4 no
C9 . C11 H112 107.5 no
C12 . C11 H112 108.8 no
H111 . C11 H112 109.0 no
C11 . C12 C13 111.0(6) yes
C11 . C12 H122 109.3 no
C13 . C12 H122 109.7 no
C11 . C12 H121 108.1 no
C13 . C12 H121 109.7 no
H122 . C12 H121 108.9 no
C12 . C13 O14 109.9(6) yes
C12 . C13 C15 115.1(5) yes
O14 . C13 C15 109.5(6) yes
C12 . C13 H131 107.5 no
O14 . C13 H131 107.7 no
C15 . C13 H131 106.8 no
C13 . C15 C16 105.2(5) yes
C13 . C15 C23 110.6(6) yes
C16 . C15 C23 114.8(6) yes
C13 . C15 C24 108.5(6) yes
C16 . C15 C24 108.5(5) yes
C23 . C15 C24 109.1(6) yes
C9 . C16 C15 117.1(5) yes
C9 . C16 C17 109.3(5) yes
C15 . C16 C17 115.1(5) yes
C9 . C16 H161 103.2 no
C15 . C16 H161 105.0 no
C17 . C16 H161 105.7 no
C16 . C17 C18 109.3(5) yes
C16 . C17 H172 109.3 no
C18 . C17 H172 109.8 no
C16 . C17 H171 109.4 no
C18 . C17 H171 109.4 no
H172 . C17 H171 109.7 no
C7 . C18 C17 113.3(6) yes
C7 . C18 O19 107.1(5) yes
C17 . C18 O19 108.5(5) yes
C7 . C18 H181 109.3 no
C17 . C18 H181 108.9 no
O19 . C18 H181 109.7 no
C18 . O19 C20 117.3(5) yes
O19 . C20 O21 122.5(7) yes
O19 . C20 C1 111.0(7) yes
O21 . C20 C1 126.5(7) yes
C20 . C1 H13 109.3 no
C20 . C1 H12 109.9 no
H13 . C1 H12 109.5 no
C20 . C1 H11 109.6 no
H13 . C1 H11 109.4 no
H12 . C1 H11 109.2 no
C15 . C23 H232 109.6 no
C15 . C23 H231 110.4 no
H232 . C23 H231 109.6 no
C15 . C23 H233 109.1 no
H232 . C23 H233 109.1 no
H231 . C23 H233 109.1 no
C15 . C24 H242 109.2 no
C15 . C24 H241 110.9 no
H242 . C24 H241 108.7 no
C15 . C24 H243 110.3 no
H242 . C24 H243 108.7 no
H241 . C24 H243 109.0 no
C7 . C25 H253 108.9 no
C7 . C25 H252 109.6 no
H253 . C25 H252 109.6 no
C7 . C25 H251 109.8 no
H253 . C25 H251 109.4 no
H252 . C25 H251 109.5 no
C3 . C26 C27 105.6(5) yes
C3 . C26 C32 107.7(5) yes
C27 . C26 C32 109.3(5) yes
C3 . C26 C37 111.8(5) yes
C27 . C26 C37 114.1(6) yes
C32 . C26 C37 108.2(5) yes
C26 . C27 C28 117.1(5) yes
C26 . C27 C35 111.5(5) yes
C28 . C27 C35 115.6(5) yes
C26 . C27 H271 103.8 no
C28 . C27 H271 102.5 no
C35 . C27 H271 104.3 no
C27 . C28 C29 107.2(6) yes
C27 . C28 C33 109.8(6) yes
C29 . C28 C33 108.3(6) yes
C27 . C28 C34 113.1(5) yes
C29 . C28 C34 110.6(6) yes
C33 . C28 C34 107.8(6) yes
C28 . C29 O30 113.9(6) yes
C28 . C29 C31 114.6(6) yes
O30 . C29 C31 108.8(6) yes
C28 . C29 H291 106.4 no
O30 . C29 H291 106.0 no
C31 . C29 H291 106.5 no
C29 . C31 C32 111.7(6) yes
C29 . C31 H312 109.4 no
C32 . C31 H312 109.6 no
C29 . C31 H311 108.4 no
C32 . C31 H311 108.2 no
H312 . C31 H311 109.5 no
C26 . C32 C31 112.5(6) yes
C26 . C32 H322 108.1 no
C31 . C32 H322 108.2 no
C26 . C32 H321 108.4 no
C31 . C32 H321 110.2 no
H322 . C32 H321 109.4 no
C28 . C33 H331 110.4 no
C28 . C33 H333 108.7 no
H331 . C33 H333 110.3 no
C28 . C33 H332 108.8 no
H331 . C33 H332 109.7 no
H333 . C33 H332 108.8 no
C28 . C34 H341 109.4 no
C28 . C34 H342 109.6 no
H341 . C34 H342 109.0 no
C28 . C34 H343 108.9 no
H341 . C34 H343 109.8 no
H342 . C34 H343 110.2 no
C27 . C35 C36 111.9(6) yes
C27 . C35 H351 109.4 no
C36 . C35 H351 109.9 no
C27 . C35 H352 107.3 no
C36 . C35 H352 109.3 no
H351 . C35 H352 109.0 no
C35 . C36 C2 112.4(5) yes
C35 . C36 H362 107.4 no
C2 . C36 H362 107.8 no
C35 . C36 H361 109.9 no
C2 . C36 H361 110.6 no
H362 . C36 H361 108.6 no
C26 . C37 H371 108.8 no
C26 . C37 H373 110.0 no
H371 . C37 H373 109.6 no
C26 . C37 H372 109.7 no
H371 . C37 H372 108.9 no
H373 . C37 H372 109.8 no
C2 . C38 H381 109.9 no
C2 . C38 H383 109.2 no
H381 . C38 H383 109.2 no
C2 . C38 H382 108.9 no
H381 . C38 H382 109.8 no
H383 . C38 H382 109.8 no
H422 3_756 O42 H422 140.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.457(7) yes
O1 C6 . 1.431(8) yes
C2 C3 . 1.541(9) yes
C2 C36 . 1.521(9) yes
C2 C38 . 1.534(9) yes
C3 C4 . 1.543(9) yes
C3 C26 . 1.556(9) yes
C3 H31 . 0.982 no
C4 C5 . 1.536(9) yes
C4 H42 . 0.976 no
C4 H41 . 0.977 no
C5 C6 . 1.521(9) yes
C5 H51 . 0.968 no
C5 H52 . 0.969 no
C6 C7 . 1.547(9) yes
C6 H61 . 0.987 no
C7 O8 . 1.430(8) yes
C7 C18 . 1.565(9) yes
C7 C25 . 1.531(9) yes
O8 C9 . 1.466(7) yes
C9 C10 . 1.541(9) yes
C9 C11 . 1.513(9) yes
C9 C16 . 1.533(9) yes
C10 H101 . 0.961 no
C10 H103 . 0.963 no
C10 H102 . 0.962 no
C11 C12 . 1.518(9) yes
C11 H111 . 0.972 no
C11 H112 . 0.972 no
C12 C13 . 1.535(9) yes
C12 H122 . 0.963 no
C12 H121 . 0.964 no
C13 O14 . 1.455(8) yes
C13 C15 . 1.534(10) yes
C13 H131 . 0.977 no
C15 C16 . 1.575(9) yes
C15 C23 . 1.543(10) yes
C15 C24 . 1.513(9) yes
C16 C17 . 1.528(9) yes
C16 H161 . 0.981 no
C17 C18 . 1.484(9) yes
C17 H172 . 0.975 no
C17 H171 . 0.969 no
C18 O19 . 1.478(7) yes
C18 H181 . 0.979 no
O19 C20 . 1.338(9) yes
C20 O21 . 1.198(9) yes
C20 C1 . 1.496(10) yes
C1 H13 . 0.962 no
C1 H12 . 0.963 no
C1 H11 . 0.959 no
C23 H232 . 0.954 no
C23 H231 . 0.963 no
C23 H233 . 0.958 no
C24 H242 . 0.959 no
C24 H241 . 0.963 no
C24 H243 . 0.962 no
C25 H253 . 0.962 no
C25 H252 . 0.965 no
C25 H251 . 0.957 no
C26 C27 . 1.552(9) yes
C26 C32 . 1.542(9) yes
C26 C37 . 1.535(10) yes
C27 C28 . 1.557(9) yes
C27 C35 . 1.524(9) yes
C27 H271 . 0.979 no
C28 C29 . 1.532(10) yes
C28 C33 . 1.522(10) yes
C28 C34 . 1.541(10) yes
C29 O30 . 1.434(8) yes
C29 C31 . 1.509(10) yes
C29 H291 . 0.977 no
C31 C32 . 1.531(9) yes
C31 H312 . 0.973 no
C31 H311 . 0.973 no
C32 H322 . 0.978 no
C32 H321 . 0.961 no
C33 H331 . 0.957 no
C33 H333 . 0.969 no
C33 H332 . 0.962 no
C34 H341 . 0.958 no
C34 H342 . 0.958 no
C34 H343 . 0.964 no
C35 C36 . 1.557(9) yes
C35 H351 . 0.969 no
C35 H352 . 0.974 no
C36 H362 . 0.966 no
C36 H361 . 0.969 no
C37 H371 . 0.960 no
C37 H373 . 0.959 no
C37 H372 . 0.957 no
C38 H381 . 0.962 no
C38 H383 . 0.961 no
C38 H382 . 0.959 no
O42 H422 3_756 0.817 no
O42 H422 . 0.817 no
|
1502003.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502003.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502003
loop_
_publ_author_name
'Abbet, Christian'
'Neuburger, Markus'
'Wagner, Trixie'
'Quitschau, Melanie'
'Hamburger, Matthias'
'Potterat, Olivier'
_publ_section_title
;
Phyteumosides A and B: new saponins with unique triterpenoid aglycons
from Phyteuma orbiculare L.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1354
_journal_page_last 1357
_journal_paper_doi 10.1021/ol200047v
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C32 H56 O7, 7(H2 O)'
_chemical_formula_sum 'C32 H70 O14'
_chemical_formula_weight 678.90
_space_group_IT_number 5
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'C 2y'
_symmetry_space_group_name_H-M 'C 1 2 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_cell_angle_alpha 90
_cell_angle_beta 105.051(4)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 50.084(4)
_cell_length_b 5.9938(6)
_cell_length_c 13.2247(10)
_cell_measurement_reflns_used 0
_cell_measurement_temperature 173
_cell_measurement_theta_max 0
_cell_measurement_theta_min 0
_cell_volume 3833.8(6)
_computing_cell_refinement 'SAINT (Siemens ,1995)'
_computing_data_collection 'SMART (Siemens, 1993)'
_computing_data_reduction 'SAINT (Siemens ,1995)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature 173
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device Area
_diffrn_measurement_device_type 'Bruker SMART'
_diffrn_measurement_method '\f & \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54180
_diffrn_reflns_av_R_equivalents 0.069
_diffrn_reflns_limit_h_max 58
_diffrn_reflns_limit_h_min -59
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 23579
_diffrn_reflns_theta_full 32.828
_diffrn_reflns_theta_max 66.997
_diffrn_reflns_theta_min 1.827
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.749
_exptl_absorpt_correction_T_max 0.99
_exptl_absorpt_correction_T_min 0.93
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.18
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1456
_exptl_crystal_size_max 0.250
_exptl_crystal_size_mid 0.150
_exptl_crystal_size_min 0.010
_refine_diff_density_max 0.70
_refine_diff_density_min -0.70
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack 0.2(3)
_refine_ls_extinction_method None
_refine_ls_goodness_of_fit_ref 0.9263
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 443
_refine_ls_number_reflns 4707
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1040
_refine_ls_R_factor_gt 0.0833
_refine_ls_shift/su_max 0.0012236
_refine_ls_shift/su_mean 0.0000568
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.25 1.00 0.699
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.1160
_refine_ls_wR_factor_gt 0.0862
_refine_ls_wR_factor_ref 0.0862
_reflns_limit_h_max 56
_reflns_limit_h_min -59
_reflns_limit_k_max 6
_reflns_limit_k_min -7
_reflns_limit_l_max 15
_reflns_limit_l_min 0
_reflns_number_gt 4707
_reflns_number_total 6224
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_oxford_refine_ls_r_factor_ref 0.0833
_oxford_refine_ls_scale 0.2546(8)
_oxford_reflns_number_all 6198
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file ol200047v_si_002.cif
_cod_data_source_block 2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'C 2'
_cod_database_code 1502003
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
-x,y,-z
-x+1/2,y+1/2,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.67487(5) 0.9509(5) 0.16262(19) 0.0374 1.0000 Uani .
C2 C 0.69994(7) 0.8296(7) 0.2102(3) 0.0312 1.0000 Uani .
C3 C 0.72139(8) 0.8863(7) 0.1477(3) 0.0321 1.0000 Uani .
C4 C 0.70972(8) 0.8333(8) 0.0312(3) 0.0370 1.0000 Uani .
C5 C 0.68209(9) 0.9523(8) -0.0108(3) 0.0414 1.0000 Uani .
C6 C 0.66264(8) 0.8906(8) 0.0557(3) 0.0386 1.0000 Uani .
C7 C 0.63342(9) 0.9932(8) 0.0239(3) 0.0447 1.0000 Uani .
O8 O 0.62136(6) 0.8958(6) -0.0774(2) 0.0497 1.0000 Uani .
C9 C 0.63363(10) 1.2429(9) 0.0170(4) 0.0511 1.0000 Uani .
C10 C 0.61750(9) 0.9056(9) 0.1010(3) 0.0459 1.0000 Uani .
O11 O 0.61958(7) 1.0721(7) 0.1816(2) 0.0531 1.0000 Uani .
C12 C 0.62735(10) 1.0164(10) 0.2830(4) 0.0576 1.0000 Uani .
O13 O 0.63339(8) 0.8269(7) 0.3128(3) 0.0636 1.0000 Uani .
C14 C 0.62617(17) 1.2093(13) 0.3500(5) 0.0957 1.0000 Uani .
C15 C 0.58665(10) 0.8667(11) 0.0519(4) 0.0617 1.0000 Uani .
C16 C 0.57255(10) 0.7687(11) 0.1281(4) 0.0662 1.0000 Uani .
C17 C 0.55397(12) 0.8587(12) 0.1686(5) 0.0723 1.0000 Uani .
C18 C 0.54468(19) 1.0992(16) 0.1511(8) 0.1196 1.0000 Uani .
C19 C 0.54133(13) 0.7331(14) 0.2421(5) 0.0819 1.0000 Uani .
C20 C 0.51042(12) 0.6973(13) 0.2000(5) 0.0755 1.0000 Uani .
C21 C 0.49792(12) 0.5447(15) 0.2673(4) 0.0857 1.0000 Uani .
O22 O 0.50301(10) 0.6349(13) 0.3713(4) 0.1226 1.0000 Uani .
C23 C 0.46755(11) 0.4961(12) 0.2248(4) 0.0730 1.0000 Uani .
O24 O 0.46011(8) 0.3364(9) 0.2947(3) 0.0877 1.0000 Uani .
C25 C 0.44948(12) 0.6999(13) 0.2210(5) 0.0807 1.0000 Uani .
C26 C 0.46176(14) 0.3828(13) 0.1202(5) 0.0838 1.0000 Uani .
C27 C 0.69298(9) 0.5834(7) 0.2160(3) 0.0388 1.0000 Uani .
C28 C 0.71038(7) 0.9240(8) 0.3198(3) 0.0336 1.0000 Uani .
C29 C 0.73993(8) 0.8493(7) 0.3740(3) 0.0329 1.0000 Uani .
C30 C 0.76049(8) 0.9086(7) 0.3100(3) 0.0317 1.0000 Uani .
C31 C 0.75147(8) 0.8035(7) 0.1980(3) 0.0304 1.0000 Uani .
C32 C 0.75335(9) 0.5460(7) 0.1950(3) 0.0363 1.0000 Uani .
C33 C 0.77079(8) 0.9011(7) 0.1349(3) 0.0351 1.0000 Uani .
C34 C 0.80126(8) 0.8784(8) 0.1896(3) 0.0380 1.0000 Uani .
C35 C 0.80846(8) 0.9766(8) 0.2981(3) 0.0369 1.0000 Uani .
O36 O 0.83770(6) 0.9537(6) 0.3437(2) 0.0467 1.0000 Uani .
C37 C 0.79126(8) 0.8805(7) 0.3704(3) 0.0298 1.0000 Uani .
C38 C 0.80011(8) 0.6393(7) 0.4039(3) 0.0380 1.0000 Uani .
C39 C 0.79746(8) 1.0234(7) 0.4702(3) 0.0360 1.0000 Uani .
O40 O 0.62467(10) 0.5607(8) -0.2202(4) 0.0950 1.0000 Uani .
O41 O 0.59538(8) 1.1787(7) -0.2343(3) 0.0671 1.0000 Uani .
O42 O 0.63216(8) 0.7383(8) 0.5156(3) 0.0767 1.0000 Uani .
O43 O 0.63986(18) 1.0508(13) 0.6720(6) 0.1149 0.7500 Uani .
O44 O 0.5841(2) 0.672(4) 0.5615(10) 0.1481 0.5000 Uani .
O45 O 0.5857(2) 0.900(3) 0.5691(9) 0.1104 0.5000 Uani .
O46 O 0.54736(18) 0.490(3) 0.5203(5) 0.2152 0.8000 Uani .
O47 O 0.55868(19) 1.163(3) 0.4412(8) 0.1283 0.5000 Uani .
O48 O 0.5371(6) 0.863(7) 0.509(3) 0.1156 0.1500 Uani .
O49 O 0.50230(13) 1.0623(15) 0.3992(5) 0.1097 0.8000 Uani .
H31 H 0.7227 1.0496 0.1500 0.0369 1.0000 Uiso R
H41 H 0.7227 0.8774 -0.0081 0.0449 1.0000 Uiso R
H42 H 0.7068 0.6722 0.0226 0.0444 1.0000 Uiso R
H51 H 0.6848 1.1132 -0.0100 0.0497 1.0000 Uiso R
H52 H 0.6742 0.9026 -0.0816 0.0498 1.0000 Uiso R
H61 H 0.6604 0.7271 0.0509 0.0480 1.0000 Uiso R
H81 H 0.6108 0.9883 -0.1139 0.0758 1.0000 Uiso R
H91 H 0.6449 1.3046 0.0809 0.0716 1.0000 Uiso R
H92 H 0.6413 1.2886 -0.0389 0.0718 1.0000 Uiso R
H93 H 0.6150 1.2997 0.0046 0.0718 1.0000 Uiso R
H101 H 0.6258 0.7657 0.1329 0.0489 1.0000 Uiso R
H141 H 0.6346 1.3350 0.3250 0.1491 1.0000 Uiso R
H143 H 0.6074 1.2460 0.3499 0.1491 1.0000 Uiso R
H142 H 0.6366 1.1757 0.4205 0.1490 1.0000 Uiso R
H151 H 0.5782 1.0089 0.0267 0.0758 1.0000 Uiso R
H152 H 0.5843 0.7649 -0.0069 0.0760 1.0000 Uiso R
H161 H 0.5788 0.6273 0.1543 0.0920 1.0000 Uiso R
H182 H 0.5282 1.1042 0.0939 0.1969 1.0000 Uiso R
H181 H 0.5405 1.1591 0.2122 0.1969 1.0000 Uiso R
H183 H 0.5589 1.1882 0.1344 0.1970 1.0000 Uiso R
H192 H 0.5447 0.8204 0.3056 0.1117 1.0000 Uiso R
H191 H 0.5500 0.5874 0.2572 0.1118 1.0000 Uiso R
H201 H 0.5014 0.8415 0.1961 0.0961 1.0000 Uiso R
H202 H 0.5068 0.6358 0.1299 0.0958 1.0000 Uiso R
H211 H 0.5079 0.4010 0.2734 0.1090 1.0000 Uiso R
H221 H 0.4877 0.6643 0.3797 0.1800 1.0000 Uiso R
H241 H 0.4541 0.4160 0.3346 0.1409 1.0000 Uiso R
H252 H 0.4303 0.6605 0.1916 0.1238 1.0000 Uiso R
H251 H 0.4550 0.8125 0.1782 0.1239 1.0000 Uiso R
H253 H 0.4518 0.7588 0.2904 0.1240 1.0000 Uiso R
H261 H 0.4756 0.2678 0.1236 0.1239 1.0000 Uiso R
H262 H 0.4624 0.4898 0.0663 0.1240 1.0000 Uiso R
H263 H 0.4436 0.3156 0.1064 0.1240 1.0000 Uiso R
H272 H 0.7071 0.5093 0.2672 0.0599 1.0000 Uiso R
H271 H 0.6758 0.5680 0.2346 0.0600 1.0000 Uiso R
H273 H 0.6915 0.5125 0.1501 0.0599 1.0000 Uiso R
H282 H 0.6980 0.8745 0.3604 0.0418 1.0000 Uiso R
H281 H 0.7099 1.0862 0.3162 0.0420 1.0000 Uiso R
H291 H 0.7458 0.9261 0.4402 0.0408 1.0000 Uiso R
H292 H 0.7405 0.6887 0.3855 0.0407 1.0000 Uiso R
H301 H 0.7583 1.0700 0.2972 0.0426 1.0000 Uiso R
H332 H 0.7670 0.8262 0.0688 0.0389 1.0000 Uiso R
H331 H 0.7667 1.0606 0.1240 0.0387 1.0000 Uiso R
H341 H 0.8117 0.9544 0.1482 0.0489 1.0000 Uiso R
H342 H 0.8061 0.7209 0.1948 0.0486 1.0000 Uiso R
H351 H 0.8041 1.1370 0.2911 0.0444 1.0000 Uiso R
H361 H 0.8480 0.8820 0.3180 0.0728 1.0000 Uiso R
H382 H 0.7873 0.5709 0.4380 0.0594 1.0000 Uiso R
H383 H 0.8184 0.6392 0.4506 0.0598 1.0000 Uiso R
H381 H 0.8004 0.5530 0.3430 0.0599 1.0000 Uiso R
H393 H 0.7884 0.9569 0.5187 0.0487 1.0000 Uiso R
H392 H 0.8170 1.0302 0.5025 0.0490 1.0000 Uiso R
H391 H 0.7905 1.1743 0.4538 0.0487 1.0000 Uiso R
H321 H 0.7494 0.4813 0.2555 0.0518 1.0000 Uiso R
H402 H 0.6373 0.6191 -0.2382 0.1509 1.0000 Uiso R
H323 H 0.7403 0.4892 0.1344 0.0518 1.0000 Uiso R
H401 H 0.6282 0.6444 -0.1694 0.1509 1.0000 Uiso R
H322 H 0.7714 0.5000 0.1932 0.0517 1.0000 Uiso R
H412 H 0.5854 1.2766 -0.2687 0.1002 1.0000 Uiso R
H411 H 0.5844 1.0803 -0.2606 0.1001 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0372(15) 0.0457(18) 0.0302(13) -0.0008(12) 0.0103(11) -0.0030(12)
C2 0.0277(19) 0.036(2) 0.0305(18) 0.0046(16) 0.0084(15) 0.0000(16)
C3 0.045(2) 0.026(2) 0.0268(17) 0.0037(14) 0.0121(15) -0.0018(17)
C4 0.044(2) 0.045(3) 0.0237(17) -0.0002(16) 0.0116(15) -0.0054(18)
C5 0.048(2) 0.045(3) 0.0293(19) 0.0005(17) 0.0078(17) -0.0074(19)
C6 0.042(2) 0.043(3) 0.0289(18) 0.0030(17) 0.0059(16) -0.0004(19)
C7 0.043(2) 0.050(3) 0.040(2) 0.0011(19) 0.0075(18) -0.010(2)
O8 0.0466(17) 0.059(2) 0.0373(14) -0.0006(14) 0.0000(12) -0.0075(15)
C9 0.042(2) 0.059(3) 0.049(2) 0.014(2) 0.0065(19) 0.003(2)
C10 0.041(2) 0.056(3) 0.042(2) -0.002(2) 0.0117(18) -0.003(2)
O11 0.0511(18) 0.064(2) 0.0453(17) -0.0012(15) 0.0150(14) -0.0052(16)
C12 0.054(3) 0.070(4) 0.045(3) 0.009(2) 0.006(2) -0.002(3)
O13 0.064(2) 0.075(3) 0.0515(18) 0.0116(18) 0.0150(16) 0.0065(19)
C14 0.141(7) 0.091(5) 0.053(3) -0.010(3) 0.019(4) 0.000(5)
C15 0.046(3) 0.086(4) 0.052(3) -0.003(3) 0.011(2) -0.004(3)
C16 0.037(3) 0.087(4) 0.074(3) 0.007(3) 0.014(2) -0.007(3)
C17 0.060(3) 0.092(5) 0.069(3) 0.003(3) 0.024(3) -0.001(3)
C18 0.115(6) 0.120(7) 0.145(7) 0.037(6) 0.072(6) 0.035(5)
C19 0.066(4) 0.119(6) 0.067(3) 0.015(4) 0.028(3) -0.003(4)
C20 0.055(3) 0.111(5) 0.060(3) 0.008(3) 0.014(3) -0.002(3)
C21 0.059(3) 0.145(7) 0.055(3) 0.009(4) 0.019(3) 0.003(4)
O22 0.065(3) 0.235(8) 0.068(3) 0.011(4) 0.017(2) -0.031(4)
C23 0.048(3) 0.112(5) 0.058(3) 0.011(3) 0.014(2) -0.007(3)
O24 0.058(2) 0.128(4) 0.080(3) 0.035(3) 0.022(2) 0.008(2)
C25 0.053(3) 0.109(5) 0.081(4) 0.000(4) 0.019(3) -0.001(3)
C26 0.075(4) 0.102(5) 0.080(4) -0.010(4) 0.031(3) -0.013(4)
C27 0.046(2) 0.038(2) 0.0349(19) 0.0033(17) 0.0153(17) -0.0093(19)
C28 0.0295(19) 0.042(2) 0.0323(19) -0.0019(16) 0.0138(15) -0.0032(17)
C29 0.043(2) 0.029(2) 0.0292(17) -0.0032(15) 0.0129(16) 0.0002(17)
C30 0.043(2) 0.030(2) 0.0241(17) -0.0001(15) 0.0124(16) 0.0007(17)
C31 0.043(2) 0.026(2) 0.0243(17) -0.0002(15) 0.0127(15) -0.0042(16)
C32 0.053(2) 0.025(2) 0.0342(19) -0.0048(15) 0.0186(17) -0.0018(17)
C33 0.049(2) 0.035(2) 0.0268(17) -0.0024(16) 0.0190(16) -0.0025(18)
C34 0.046(2) 0.040(2) 0.0333(19) 0.0004(17) 0.0202(17) 0.0020(18)
C35 0.037(2) 0.038(2) 0.040(2) 0.0021(17) 0.0163(17) -0.0017(17)
O36 0.0341(15) 0.064(2) 0.0447(16) -0.0063(14) 0.0152(12) -0.0012(14)
C37 0.0333(19) 0.030(2) 0.0283(17) 0.0010(15) 0.0112(15) 0.0016(16)
C38 0.039(2) 0.039(2) 0.035(2) 0.0011(16) 0.0067(17) 0.0036(17)
C39 0.039(2) 0.036(2) 0.0343(19) -0.0060(16) 0.0115(16) -0.0037(17)
O40 0.111(4) 0.087(3) 0.116(4) -0.005(3) 0.081(3) -0.011(3)
O41 0.067(2) 0.077(3) 0.0535(19) 0.0063(18) 0.0087(17) 0.012(2)
O42 0.071(3) 0.104(3) 0.060(2) 0.021(2) 0.0247(18) 0.027(2)
O43 0.159(7) 0.088(5) 0.131(6) -0.022(4) 0.098(5) -0.025(5)
O44 0.051(6) 0.29(2) 0.110(9) 0.062(12) 0.026(5) 0.015(9)
O45 0.109(9) 0.132(10) 0.095(7) 0.026(7) 0.034(6) 0.016(8)
O46 0.117(6) 0.46(2) 0.070(4) 0.058(8) 0.035(4) 0.109(10)
O47 0.066(6) 0.228(15) 0.099(7) -0.043(9) 0.036(5) 0.001(8)
O48 0.051(16) 0.14(3) 0.15(3) -0.05(3) 0.022(18) -0.020(19)
O49 0.086(4) 0.148(6) 0.095(4) 0.017(4) 0.025(3) 0.013(4)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C6 113.8(3) yes
O1 C2 C3 107.5(3) yes
O1 C2 C27 109.0(3) yes
C3 C2 C27 115.9(3) yes
O1 C2 C28 105.9(3) yes
C3 C2 C28 108.2(3) yes
C27 C2 C28 109.9(3) yes
C2 C3 C4 110.7(3) yes
C2 C3 C31 115.3(3) yes
C4 C3 C31 115.8(3) yes
C2 C3 H31 104.6 no
C4 C3 H31 104.1 no
C31 C3 H31 104.7 no
C3 C4 C5 110.0(3) yes
C3 C4 H41 110.4 no
C5 C4 H41 110.4 no
C3 C4 H42 109.1 no
C5 C4 H42 108.9 no
H41 C4 H42 107.9 no
C4 C5 C6 109.4(3) yes
C4 C5 H51 110.4 no
C6 C5 H51 110.0 no
C4 C5 H52 108.3 no
C6 C5 H52 108.9 no
H51 C5 H52 109.8 no
C5 C6 O1 109.6(3) yes
C5 C6 C7 116.8(3) yes
O1 C6 C7 107.5(3) yes
C5 C6 H61 106.6 no
O1 C6 H61 109.0 no
C7 C6 H61 107.1 no
C6 C7 O8 103.4(3) yes
C6 C7 C9 113.2(4) yes
O8 C7 C9 110.8(4) yes
C6 C7 C10 107.5(4) yes
O8 C7 C10 108.2(3) yes
C9 C7 C10 113.2(4) yes
C7 O8 H81 108.6 no
C7 C9 H91 110.0 no
C7 C9 H92 110.0 no
H91 C9 H92 107.9 no
C7 C9 H93 109.9 no
H91 C9 H93 109.5 no
H92 C9 H93 109.4 no
C7 C10 O11 107.6(4) yes
C7 C10 C15 114.2(4) yes
O11 C10 C15 106.9(4) yes
C7 C10 H101 109.9 no
O11 C10 H101 109.4 no
C15 C10 H101 108.7 no
C10 O11 C12 120.9(4) yes
O11 C12 O13 122.8(5) yes
O11 C12 C14 111.2(5) yes
O13 C12 C14 125.9(5) yes
C12 C14 H141 108.6 no
C12 C14 H143 111.7 no
H141 C14 H143 109.5 no
C12 C14 H142 108.8 no
H141 C14 H142 108.7 no
H143 C14 H142 109.4 no
C10 C15 C16 112.1(4) yes
C10 C15 H151 108.3 no
C16 C15 H151 109.7 no
C10 C15 H152 109.4 no
C16 C15 H152 108.3 no
H151 C15 H152 109.0 no
C15 C16 C17 128.8(6) yes
C15 C16 H161 115.6 no
C17 C16 H161 115.4 no
C16 C17 C18 123.7(6) yes
C16 C17 C19 121.7(7) yes
C18 C17 C19 114.5(6) yes
C17 C18 H182 108.4 no
C17 C18 H181 110.8 no
H182 C18 H181 108.8 no
C17 C18 H183 110.3 no
H182 C18 H183 109.6 no
H181 C18 H183 108.9 no
C17 C19 C20 113.4(5) yes
C17 C19 H192 106.5 no
C20 C19 H192 109.2 no
C17 C19 H191 110.1 no
C20 C19 H191 108.0 no
H192 C19 H191 109.8 no
C19 C20 C21 113.9(5) yes
C19 C20 H201 107.9 no
C21 C20 H201 108.1 no
C19 C20 H202 109.0 no
C21 C20 H202 109.1 no
H201 C20 H202 108.6 no
C20 C21 O22 109.7(6) yes
C20 C21 C23 115.3(5) yes
O22 C21 C23 109.9(5) yes
C20 C21 H211 107.2 no
O22 C21 H211 106.8 no
C23 C21 H211 107.6 no
C21 O22 H221 105.7 no
C21 C23 O24 107.0(5) yes
C21 C23 C25 113.2(6) yes
O24 C23 C25 107.7(5) yes
C21 C23 C26 111.5(5) yes
O24 C23 C26 105.6(6) yes
C25 C23 C26 111.4(5) yes
C23 O24 H241 102.9 no
C23 C25 H252 109.9 no
C23 C25 H251 108.9 no
H252 C25 H251 109.9 no
C23 C25 H253 110.0 no
H252 C25 H253 109.5 no
H251 C25 H253 108.7 no
C23 C26 H261 108.3 no
C23 C26 H262 110.1 no
H261 C26 H262 110.3 no
C23 C26 H263 108.0 no
H261 C26 H263 109.8 no
H262 C26 H263 110.2 no
C2 C27 H272 110.4 no
C2 C27 H271 109.8 no
H272 C27 H271 108.8 no
C2 C27 H273 110.5 no
H272 C27 H273 108.0 no
H271 C27 H273 109.2 no
C2 C28 C29 112.9(3) yes
C2 C28 H282 107.7 no
C29 C28 H282 109.3 no
C2 C28 H281 109.2 no
C29 C28 H281 108.8 no
H282 C28 H281 108.8 no
C28 C29 C30 112.3(3) yes
C28 C29 H291 108.4 no
C30 C29 H291 107.4 no
C28 C29 H292 110.3 no
C30 C29 H292 108.6 no
H291 C29 H292 109.8 no
C29 C30 C31 111.0(3) yes
C29 C30 C37 114.2(3) yes
C31 C30 C37 116.7(3) yes
C29 C30 H301 105.2 no
C31 C30 H301 104.0 no
C37 C30 H301 104.2 no
C3 C31 C30 106.5(3) yes
C3 C31 C32 111.4(3) yes
C30 C31 C32 114.9(3) yes
C3 C31 C33 108.7(3) yes
C30 C31 C33 106.9(3) yes
C32 C31 C33 108.3(3) yes
C31 C32 H321 110.9 no
C31 C32 H323 110.1 no
H321 C32 H323 108.2 no
C31 C32 H322 110.7 no
H321 C32 H322 107.8 no
H323 C32 H322 109.0 no
C31 C33 C34 113.7(3) yes
C31 C33 H332 108.2 no
C34 C33 H332 109.2 no
C31 C33 H331 108.2 no
C34 C33 H331 107.7 no
H332 C33 H331 109.8 no
C33 C34 C35 112.5(3) yes
C33 C34 H341 108.4 no
C35 C34 H341 108.9 no
C33 C34 H342 108.8 no
C35 C34 H342 108.6 no
H341 C34 H342 109.7 no
C34 C35 O36 109.2(3) yes
C34 C35 C37 114.1(3) yes
O36 C35 C37 111.9(3) yes
C34 C35 H351 107.4 no
O36 C35 H351 108.1 no
C37 C35 H351 105.9 no
C35 O36 H361 124.4 no
C30 C37 C35 106.1(3) yes
C30 C37 C38 115.0(3) yes
C35 C37 C38 111.1(3) yes
C30 C37 C39 109.6(3) yes
C35 C37 C39 107.5(3) yes
C38 C37 C39 107.3(3) yes
C37 C38 H382 110.8 no
C37 C38 H383 109.8 no
H382 C38 H383 109.6 no
C37 C38 H381 109.3 no
H382 C38 H381 108.5 no
H383 C38 H381 108.8 no
C37 C39 H393 108.4 no
C37 C39 H392 111.2 no
H393 C39 H392 108.8 no
C37 C39 H391 110.3 no
H393 C39 H391 109.1 no
H392 C39 H391 108.9 no
H402 O40 H401 87.4 no
H412 O41 H411 92.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.446(5) yes
O1 C6 1.434(5) yes
C2 C3 1.554(5) yes
C2 C27 1.523(6) yes
C2 C28 1.516(5) yes
C3 C4 1.532(5) yes
C3 C31 1.562(6) yes
C3 H31 0.981 no
C4 C5 1.528(6) yes
C4 H41 0.967 no
C4 H42 0.979 no
C5 C6 1.518(5) yes
C5 H51 0.973 no
C5 H52 0.964 no
C6 C7 1.542(6) yes
C6 H61 0.987 no
C7 O8 1.442(5) yes
C7 C9 1.500(7) yes
C7 C10 1.541(6) yes
O8 H81 0.830 no
C9 H91 0.960 no
C9 H92 0.958 no
C9 H93 0.964 no
C10 O11 1.444(6) yes
C10 C15 1.530(7) yes
C10 H101 0.981 no
O11 C12 1.338(6) yes
C12 O13 1.215(7) yes
C12 C14 1.467(9) yes
C14 H141 0.962 no
C14 H143 0.965 no
C14 H142 0.964 no
C15 C16 1.493(7) yes
C15 H151 0.971 no
C15 H152 0.972 no
C16 C17 1.305(8) yes
C16 H161 0.938 no
C17 C18 1.513(11) yes
C17 C19 1.494(8) yes
C18 H182 0.963 no
C18 H181 0.956 no
C18 H183 0.961 no
C19 C20 1.518(8) yes
C19 H192 0.967 no
C19 H191 0.973 no
C20 C21 1.520(9) yes
C20 H201 0.970 no
C20 H202 0.970 no
C21 O22 1.437(9) yes
C21 C23 1.507(8) yes
C21 H211 0.989 no
O22 H221 0.823 no
C23 O24 1.445(7) yes
C23 C25 1.513(10) yes
C23 C26 1.500(9) yes
O24 H241 0.824 no
C25 H252 0.968 no
C25 H251 0.966 no
C25 H253 0.962 no
C26 H261 0.970 no
C26 H262 0.966 no
C26 H263 0.969 no
C27 H272 0.954 no
C27 H271 0.957 no
C27 H273 0.954 no
C28 C29 1.534(5) yes
C28 H282 0.967 no
C28 H281 0.973 no
C29 C30 1.535(5) yes
C29 H291 0.966 no
C29 H292 0.974 no
C30 C31 1.564(5) yes
C30 C37 1.550(5) yes
C30 H301 0.983 no
C31 C32 1.547(5) yes
C31 C33 1.547(5) yes
C32 H321 0.954 no
C32 H323 0.956 no
C32 H322 0.951 no
C33 C34 1.515(6) yes
C33 H332 0.957 no
C33 H331 0.980 no
C34 C35 1.506(5) yes
C34 H341 0.965 no
C34 H342 0.973 no
C35 O36 1.438(5) yes
C35 C37 1.554(5) yes
C35 H351 0.985 no
O36 H361 0.811 no
C37 C38 1.543(6) yes
C37 C39 1.535(5) yes
C38 H382 0.967 no
C38 H383 0.962 no
C38 H381 0.959 no
C39 H393 0.964 no
C39 H392 0.961 no
C39 H391 0.974 no
O40 H402 0.812 no
O40 H401 0.820 no
O41 H412 0.825 no
O41 H411 0.821 no
O44 O45 1.37(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O8 H81 O41 . 158 0.83 1.95 2.734(7) yes
O22 H221 O48 3_656 145 0.82 2.46 3.167(7) yes
O24 H241 O46 3_656 149 0.82 1.99 2.729(7) yes
O36 H361 O40 4_655 121 0.81 2.37 2.868(7) yes
O36 H361 O43 4_646 134 0.81 2.07 2.694(7) yes
O40 H402 O36 4_645 125 0.81 2.32 2.868(7) yes
O40 H401 O8 . 156 0.82 2.02 2.791(7) yes
O41 H412 O24 3_665 130 0.83 2.25 2.846(7) yes
O41 H411 O45 1_554 121 0.82 2.51 3.023(7) yes
|
1502004.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502004.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502004
loop_
_publ_author_name
'Verma, Akhilesh Kumar'
'Joshi, Megha'
'Singh, Ved Prakash'
_publ_section_title
;
Base-mediated regio- and stereoselective intermolecular addition of
alkynes to N-heterocycles.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1630
_journal_page_last 1633
_journal_paper_doi 10.1021/ol200048z
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C24 H21 N'
_chemical_formula_sum 'C24 H21 N'
_chemical_formula_weight 323.42
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 97.18(5)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.001(5)
_cell_length_b 15.566(7)
_cell_length_c 17.278(6)
_cell_measurement_reflns_used 1304
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 24.99
_cell_measurement_theta_min 2.90
_cell_volume 1868.1(17)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'Xcalibur, Sapphire3'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.2176
_diffrn_reflns_av_sigmaI/netI 0.1963
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 7536
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 2.87
_exptl_absorpt_coefficient_mu 0.066
_exptl_absorpt_correction_T_max 0.947
_exptl_absorpt_correction_T_min 0.931
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.49b (release 14-10-2009 CrysAlis171 .NET)
(compiled Oct 14 2009,10:37:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn 1.150
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 688
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.18
_refine_diff_density_max 0.375
_refine_diff_density_min -0.367
_refine_diff_density_rms 0.080
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.032
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 229
_refine_ls_number_reflns 3271
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.032
_refine_ls_R_factor_all 0.2743
_refine_ls_R_factor_gt 0.1249
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.3094
_refine_ls_wR_factor_ref 0.3800
_reflns_number_gt 1304
_reflns_number_total 3271
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200048z_si_002.cif
_cod_data_source_block shelxl
_cod_original_cell_volume 1868.0(16)
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1502004
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 1.0271(7) 0.0703(3) 0.7742(2) 0.0542(13) Uani 1 1 d .
C24 C 0.9547(9) 0.0185(4) 0.8295(3) 0.0545(15) Uani 1 1 d .
C15 C 0.7112(9) 0.0638(4) 0.6503(3) 0.0613(16) Uani 1 1 d .
H15 H 0.7938 0.0170 0.6579 0.074 Uiso 1 1 calc R
C13 C 0.4098(9) 0.1237(4) 0.5879(3) 0.0659(17) Uani 1 1 d .
C19 C 1.0892(9) -0.0470(4) 0.8507(3) 0.0587(16) Uani 1 1 d .
C5 C 1.2149(8) 0.2441(4) 0.8089(3) 0.0565(16) Uani 1 1 d .
C4 C 1.2963(9) 0.1932(4) 0.8720(3) 0.0628(17) Uani 1 1 d .
H4 H 1.2330 0.1437 0.8849 0.075 Uiso 1 1 calc R
C10 C 0.7591(8) 0.1402(4) 0.6896(3) 0.0565(16) Uani 1 1 d .
C8 C 1.0350(9) 0.2237(4) 0.7578(3) 0.0648(18) Uani 1 1 d D
C14 C 0.5405(9) 0.0566(4) 0.5995(3) 0.0668(18) Uani 1 1 d .
H14 H 0.5137 0.0054 0.5728 0.080 Uiso 1 1 calc R
C17 C 1.2066(9) 0.0367(4) 0.7618(3) 0.0644(17) Uani 1 1 d .
H17 H 1.2867 0.0596 0.7280 0.077 Uiso 1 1 calc R
C11 C 0.6290(9) 0.2073(4) 0.6786(3) 0.0662(17) Uani 1 1 d .
H11 H 0.6561 0.2586 0.7053 0.079 Uiso 1 1 calc R
C3 C 1.4689(9) 0.2157(4) 0.9150(3) 0.0712(19) Uani 1 1 d .
H3 H 1.5178 0.1814 0.9569 0.085 Uiso 1 1 calc R
C20 C 1.0485(13) -0.1066(4) 0.9068(3) 0.078(2) Uani 1 1 d D
C9 C 0.9436(8) 0.1490(4) 0.7428(3) 0.0539(15) Uani 1 1 d .
C18 C 1.2458(10) -0.0338(4) 0.8066(3) 0.075(2) Uani 1 1 d .
H18 H 1.3555 -0.0678 0.8083 0.090 Uiso 1 1 calc R
C6 C 1.3144(8) 0.3188(4) 0.7941(3) 0.0645(16) Uiso 1 1 d .
H6 H 1.2632 0.3551 0.7541 0.077 Uiso 1 1 calc R
C12 C 0.4580(9) 0.1996(4) 0.6282(3) 0.0714(18) Uani 1 1 d .
H12 H 0.3744 0.2462 0.6215 0.086 Uiso 1 1 calc R
C23 C 0.7813(10) 0.0261(4) 0.8621(3) 0.0720(18) Uani 1 1 d .
H23 H 0.6934 0.0697 0.8471 0.086 Uiso 1 1 calc R
C2 C 1.5716(8) 0.2882(4) 0.8974(3) 0.0631(17) Uani 1 1 d .
C16 C 0.2212(9) 0.1155(5) 0.5352(4) 0.097(2) Uani 1 1 d .
H16A H 0.2117 0.0592 0.5126 0.145 Uiso 1 1 calc R
H16B H 0.2160 0.1578 0.4946 0.145 Uiso 1 1 calc R
H16C H 0.1162 0.1245 0.5652 0.145 Uiso 1 1 calc R
C7 C 1.4887(8) 0.3401(4) 0.8379(3) 0.0668(17) Uani 1 1 d .
H7 H 1.5507 0.3906 0.8267 0.080 Uiso 1 1 calc R
C22 C 0.7478(11) -0.0340(5) 0.9174(4) 0.087(2) Uani 1 1 d .
H22 H 0.6359 -0.0302 0.9411 0.104 Uiso 1 1 calc R
C21 C 0.8789(15) -0.1010(5) 0.9389(4) 0.091(2) Uani 1 1 d .
H21 H 0.8505 -0.1418 0.9751 0.109 Uiso 1 1 calc R
C1 C 1.7673(8) 0.3101(5) 0.9421(4) 0.095(2) Uani 1 1 d .
H1A H 1.8018 0.2674 0.9814 0.143 Uiso 1 1 calc R
H1B H 1.7608 0.3654 0.9663 0.143 Uiso 1 1 calc R
H1C H 1.8624 0.3115 0.9066 0.143 Uiso 1 1 calc R
H20 H 1.144(5) -0.151(2) 0.918(3) 0.054(16) Uiso 1 1 d D
H8 H 0.994(6) 0.273(2) 0.725(2) 0.046(13) Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.071(3) 0.045(3) 0.043(2) 0.000(2) -0.004(2) 0.007(3)
C24 0.075(4) 0.047(4) 0.037(3) -0.001(2) -0.013(3) -0.004(3)
C15 0.082(4) 0.048(4) 0.048(3) -0.003(3) -0.014(3) 0.005(3)
C13 0.075(4) 0.073(5) 0.046(3) 0.009(3) -0.008(3) 0.000(4)
C19 0.084(4) 0.050(4) 0.038(3) -0.002(3) -0.011(3) -0.004(3)
C5 0.073(4) 0.050(4) 0.043(3) -0.005(2) -0.008(3) -0.004(3)
C4 0.089(4) 0.046(4) 0.049(3) 0.000(3) -0.010(3) -0.008(3)
C10 0.073(4) 0.049(4) 0.043(3) 0.005(2) -0.011(3) 0.006(3)
C8 0.089(5) 0.051(4) 0.049(3) 0.003(3) -0.015(3) 0.002(4)
C14 0.088(5) 0.063(4) 0.045(3) -0.005(3) -0.011(3) -0.002(4)
C17 0.078(4) 0.063(4) 0.050(3) -0.003(3) -0.001(3) 0.004(4)
C11 0.077(4) 0.059(4) 0.059(3) -0.006(3) -0.008(3) 0.006(4)
C3 0.086(5) 0.065(4) 0.056(3) 0.003(3) -0.019(3) 0.003(4)
C20 0.116(7) 0.064(5) 0.049(3) 0.011(3) -0.013(4) -0.002(5)
C9 0.065(4) 0.051(4) 0.042(3) -0.004(2) -0.011(3) 0.003(3)
C18 0.096(5) 0.060(4) 0.063(4) 0.004(3) -0.012(4) 0.014(4)
C12 0.071(4) 0.066(4) 0.072(4) 0.012(3) -0.013(4) 0.014(3)
C23 0.073(5) 0.081(5) 0.059(3) -0.001(3) 0.000(3) -0.002(4)
C2 0.066(4) 0.072(4) 0.049(3) -0.012(3) -0.003(3) 0.002(4)
C16 0.072(5) 0.119(6) 0.088(5) 0.014(4) -0.035(4) -0.008(4)
C7 0.074(4) 0.066(4) 0.058(3) -0.005(3) -0.002(3) -0.023(3)
C22 0.091(5) 0.101(6) 0.068(4) -0.005(4) 0.012(4) -0.030(5)
C21 0.137(7) 0.084(6) 0.049(3) 0.012(4) 0.000(4) -0.023(6)
C1 0.072(5) 0.126(7) 0.083(4) -0.024(4) -0.005(4) -0.009(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C24 N1 C17 107.4(5)
C24 N1 C9 126.0(5)
C17 N1 C9 126.2(5)
N1 C24 C23 129.2(6)
N1 C24 C19 108.1(5)
C23 C24 C19 122.7(5)
C10 C15 C14 120.8(5)
C14 C13 C12 116.9(5)
C14 C13 C16 122.3(6)
C12 C13 C16 120.8(6)
C20 C19 C24 118.4(7)
C20 C19 C18 134.7(7)
C24 C19 C18 106.9(5)
C6 C5 C4 116.6(5)
C6 C5 C8 118.4(5)
C4 C5 C8 125.0(5)
C3 C4 C5 121.1(5)
C15 C10 C11 117.6(5)
C15 C10 C9 121.1(5)
C11 C10 C9 121.3(5)
C9 C8 C5 130.8(5)
C13 C14 C15 121.9(5)
C18 C17 N1 109.7(6)
C10 C11 C12 121.4(5)
C4 C3 C2 121.9(5)
C21 C20 C19 120.0(7)
C8 C9 N1 120.5(5)
C8 C9 C10 123.7(5)
N1 C9 C10 115.7(5)
C17 C18 C19 107.9(6)
C7 C6 C5 121.5(5)
C11 C12 C13 121.4(6)
C22 C23 C24 116.8(7)
C7 C2 C3 117.2(5)
C7 C2 C1 120.9(6)
C3 C2 C1 121.9(6)
C2 C7 C6 121.6(6)
C23 C22 C21 121.6(7)
C20 C21 C22 120.5(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C24 1.392(7)
N1 C17 1.402(7)
N1 C9 1.435(7)
C24 C23 1.406(8)
C24 C19 1.406(8)
C15 C10 1.389(7)
C15 C14 1.396(8)
C13 C14 1.387(8)
C13 C12 1.392(8)
C13 C16 1.512(8)
C19 C20 1.397(8)
C19 C18 1.426(9)
C5 C6 1.396(7)
C5 C4 1.408(7)
C5 C8 1.479(7)
C4 C3 1.382(7)
C10 C11 1.383(7)
C10 C9 1.495(7)
C8 C9 1.336(7)
C17 C18 1.352(7)
C11 C12 1.394(8)
C3 C2 1.391(8)
C20 C21 1.374(10)
C6 C7 1.394(8)
C23 C22 1.379(9)
C2 C7 1.378(8)
C2 C1 1.525(8)
C22 C21 1.409(10)
|
1502005.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502005.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502005
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C13 H14 N4 O4 S'
_chemical_formula_weight 322.34
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 103.887(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 9.7942(9)
_cell_length_b 12.2796(12)
_cell_length_c 12.1120(12)
_cell_measurement_reflns_used 4795
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.28
_cell_measurement_theta_min 2.40
_cell_volume 1414.1(2)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0556
_diffrn_reflns_av_sigmaI/netI 0.0450
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 9246
_diffrn_reflns_theta_full 28.32
_diffrn_reflns_theta_max 28.32
_diffrn_reflns_theta_min 2.14
_exptl_absorpt_coefficient_mu 0.254
_exptl_absorpt_correction_type none
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.514
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 672
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.453
_refine_diff_density_min -0.333
_refine_diff_density_rms 0.087
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.096
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 3412
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.096
_refine_ls_R_factor_all 0.0512
_refine_ls_R_factor_gt 0.0432
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+0.1478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1137
_refine_ls_wR_factor_ref 0.1189
_reflns_number_gt 2923
_reflns_number_total 3412
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_001.cif
_cod_data_source_block manoj1m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502005
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.49800(4) 0.18805(3) 1.01090(3) 0.02372(13) Uani 1 1 d .
O1 O 0.51178(12) 0.16698(9) 1.12843(9) 0.0295(3) Uani 1 1 d .
O2 O 0.36534(11) 0.19965(10) 0.93254(10) 0.0327(3) Uani 1 1 d .
O3 O 1.06053(11) 0.74196(9) 1.19600(9) 0.0288(3) Uani 1 1 d .
O4 O 1.03493(14) 0.91217(10) 1.13651(10) 0.0390(3) Uani 1 1 d .
N1 N 0.59007(13) 0.10020(10) 0.96239(10) 0.0252(3) Uani 1 1 d .
N2 N 0.57698(13) 0.31053(10) 1.00623(10) 0.0239(3) Uani 1 1 d .
N3 N 0.64029(13) 0.46549(11) 0.93691(11) 0.0276(3) Uani 1 1 d .
N4 N 0.88480(12) 0.67007(9) 0.98988(10) 0.0204(3) Uani 1 1 d .
C1 C 0.72373(16) 0.06520(13) 1.03864(14) 0.0306(3) Uani 1 1 d .
H1A H 0.7586 0.0003 1.0071 0.046 Uiso 1 1 calc R
H1B H 0.7084 0.0481 1.1138 0.046 Uiso 1 1 calc R
H1C H 0.7931 0.1239 1.0457 0.046 Uiso 1 1 calc R
C2 C 0.59238(19) 0.10999(15) 0.84168(14) 0.0359(4) Uani 1 1 d .
H2A H 0.6572 0.1683 0.8328 0.054 Uiso 1 1 calc R
H2B H 0.4977 0.1271 0.7965 0.054 Uiso 1 1 calc R
H2C H 0.6238 0.0410 0.8154 0.054 Uiso 1 1 calc R
C3 C 0.69569(15) 0.34671(12) 1.08345(12) 0.0241(3) Uani 1 1 d .
H3 H 0.7419 0.3122 1.1525 0.029 Uiso 1 1 calc R
C4 C 0.54970(16) 0.38538(12) 0.91890(13) 0.0275(3) Uani 1 1 d .
H4 H 0.4740 0.3795 0.8534 0.033 Uiso 1 1 calc R
C5 C 0.73347(15) 0.44179(12) 1.04101(12) 0.0227(3) Uani 1 1 d .
C6 C 0.85540(15) 0.50394(11) 1.10097(12) 0.0235(3) Uani 1 1 d .
H6 H 0.9010 0.4711 1.1711 0.028 Uiso 1 1 calc R
C7 C 0.91920(15) 0.59611(12) 1.08157(12) 0.0226(3) Uani 1 1 d .
C8 C 1.05475(16) 0.62838(13) 1.16225(13) 0.0279(3) Uani 1 1 d .
H8A H 1.0689 0.5825 1.2312 0.033 Uiso 1 1 calc R
H8B H 1.1332 0.6134 1.1259 0.033 Uiso 1 1 calc R
C9 C 1.01218(16) 0.81654(13) 1.11384(13) 0.0269(3) Uani 1 1 d .
C10 C 0.93532(14) 0.77623(12) 1.00398(12) 0.0229(3) Uani 1 1 d .
C11 C 0.88880(15) 0.83066(12) 0.90284(13) 0.0248(3) Uani 1 1 d .
H11 H 0.9071 0.9046 0.8882 0.030 Uiso 1 1 calc R
C12 C 0.80908(15) 0.75643(12) 0.82519(13) 0.0253(3) Uani 1 1 d .
H12 H 0.7646 0.7710 0.7479 0.030 Uiso 1 1 calc R
C13 C 0.80666(15) 0.65889(12) 0.88052(12) 0.0239(3) Uani 1 1 d .
H13 H 0.7589 0.5948 0.8483 0.029 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0207(2) 0.0284(2) 0.0225(2) 0.00410(13) 0.00600(14) -0.00271(13)
O1 0.0315(6) 0.0351(6) 0.0239(6) 0.0051(4) 0.0106(4) -0.0007(4)
O2 0.0229(6) 0.0412(6) 0.0321(6) 0.0097(5) 0.0028(5) -0.0042(5)
O3 0.0290(6) 0.0334(6) 0.0230(5) -0.0054(4) 0.0040(4) -0.0085(4)
O4 0.0563(8) 0.0328(6) 0.0293(6) -0.0077(5) 0.0131(6) -0.0205(6)
N1 0.0267(6) 0.0263(6) 0.0228(6) -0.0004(5) 0.0064(5) -0.0039(5)
N2 0.0241(6) 0.0244(6) 0.0223(6) 0.0028(5) 0.0039(5) -0.0003(5)
N3 0.0254(6) 0.0290(7) 0.0262(6) 0.0046(5) 0.0020(5) -0.0011(5)
N4 0.0199(6) 0.0214(6) 0.0198(6) -0.0018(4) 0.0045(4) -0.0005(4)
C1 0.0275(8) 0.0287(8) 0.0357(9) 0.0002(6) 0.0077(6) 0.0010(6)
C2 0.0424(10) 0.0424(10) 0.0250(8) -0.0042(7) 0.0124(7) -0.0057(7)
C3 0.0261(7) 0.0252(7) 0.0200(7) -0.0015(5) 0.0036(5) 0.0010(6)
C4 0.0254(7) 0.0295(8) 0.0252(7) 0.0065(6) 0.0016(6) -0.0002(6)
C5 0.0238(7) 0.0243(7) 0.0199(7) 0.0004(5) 0.0051(5) 0.0034(5)
C6 0.0246(7) 0.0249(7) 0.0195(6) -0.0002(5) 0.0023(5) 0.0035(5)
C7 0.0232(7) 0.0253(7) 0.0186(7) -0.0018(5) 0.0036(5) 0.0031(5)
C8 0.0252(7) 0.0318(8) 0.0246(7) -0.0026(6) 0.0020(6) 0.0000(6)
C9 0.0286(8) 0.0314(8) 0.0233(7) -0.0040(6) 0.0113(6) -0.0096(6)
C10 0.0203(7) 0.0251(7) 0.0248(7) -0.0034(6) 0.0084(5) -0.0043(5)
C11 0.0235(7) 0.0251(7) 0.0277(7) -0.0004(6) 0.0098(6) -0.0027(5)
C12 0.0228(7) 0.0284(8) 0.0237(7) 0.0007(6) 0.0039(5) -0.0016(6)
C13 0.0217(7) 0.0262(7) 0.0222(7) -0.0024(5) 0.0017(5) -0.0010(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 122.64(7)
O2 S1 N1 109.09(7)
O1 S1 N1 108.53(7)
O2 S1 N2 103.88(6)
O1 S1 N2 105.07(7)
N1 S1 N2 106.42(6)
C9 O3 C8 117.44(12)
C2 N1 C1 115.03(13)
C2 N1 S1 116.90(11)
C1 N1 S1 117.34(10)
C4 N2 C3 106.40(12)
C4 N2 S1 127.60(11)
C3 N2 S1 125.40(10)
C4 N3 C5 105.29(12)
C13 N4 C10 108.23(12)
C13 N4 C7 132.03(12)
C10 N4 C7 119.74(12)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C5 C3 N2 106.34(12)
C5 C3 H3 126.8
N2 C3 H3 126.8
N3 C4 N2 112.02(13)
N3 C4 H4 124.0
N2 C4 H4 124.0
C3 C5 N3 109.94(13)
C3 C5 C6 121.71(13)
N3 C5 C6 128.35(13)
C7 C6 C5 135.73(14)
C7 C6 H6 112.1
C5 C6 H6 112.1
C6 C7 N4 130.39(13)
C6 C7 C8 119.05(13)
N4 C7 C8 110.44(12)
O3 C8 C7 113.96(12)
O3 C8 H8A 108.8
C7 C8 H8A 108.8
O3 C8 H8B 108.8
C7 C8 H8B 108.8
H8A C8 H8B 107.7
O4 C9 O3 118.41(14)
O4 C9 C10 124.36(15)
O3 C9 C10 117.22(13)
C11 C10 N4 108.34(12)
C11 C10 C9 129.82(14)
N4 C10 C9 121.60(13)
C10 C11 C12 107.06(13)
C10 C11 H11 126.5
C12 C11 H11 126.5
C13 C12 C11 108.10(13)
C13 C12 H12 125.9
C11 C12 H12 125.9
N4 C13 C12 108.25(13)
N4 C13 H13 125.9
C12 C13 H13 125.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4203(11)
S1 O1 1.4211(11)
S1 N1 1.6052(13)
S1 N2 1.6984(13)
O3 C9 1.3516(19)
O3 C8 1.4507(18)
O4 C9 1.2144(19)
N1 C2 1.4725(19)
N1 C1 1.4734(19)
N2 C4 1.3782(19)
N2 C3 1.3791(18)
N3 C4 1.308(2)
N3 C5 1.3982(18)
N4 C13 1.3684(17)
N4 C10 1.3903(18)
N4 C7 1.4114(18)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C5 1.362(2)
C3 H3 0.9500
C4 H4 0.9500
C5 C6 1.456(2)
C6 C7 1.341(2)
C6 H6 0.9500
C7 C8 1.5007(19)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.450(2)
C10 C11 1.374(2)
C11 C12 1.405(2)
C11 H11 0.9500
C12 C13 1.375(2)
C12 H12 0.9500
C13 H13 0.9500
|
1502006.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502006.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502006
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C14 H17 N5 O3 S'
_chemical_formula_weight 335.39
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 93.359(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 14.707(3)
_cell_length_b 5.2984(11)
_cell_length_c 19.177(4)
_cell_measurement_reflns_used 3582
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.14
_cell_measurement_theta_min 2.77
_cell_volume 1491.8(5)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0584
_diffrn_reflns_av_sigmaI/netI 0.0697
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 9078
_diffrn_reflns_theta_full 28.29
_diffrn_reflns_theta_max 28.29
_diffrn_reflns_theta_min 1.70
_exptl_absorpt_coefficient_mu 0.241
_exptl_absorpt_correction_T_max 0.745
_exptl_absorpt_correction_T_min 0.371
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.493
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 704
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.954
_refine_diff_density_min -1.303
_refine_diff_density_rms 0.131
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 215
_refine_ls_number_reflns 3562
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.050
_refine_ls_R_factor_all 0.0752
_refine_ls_R_factor_gt 0.0665
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1250P)^2^+0.2680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1718
_refine_ls_wR_factor_ref 0.1838
_reflns_number_gt 2978
_reflns_number_total 3562
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_002.cif
_cod_data_source_block manoj5m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/n
_cod_database_code 1502006
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.69506(3) 1.40218(9) 0.61756(2) 0.0162(2) Uani 1 1 d .
O1 O 0.66070(10) 1.5701(3) 0.56438(8) 0.0205(4) Uani 1 1 d .
O2 O 0.71978(11) 1.4875(3) 0.68643(7) 0.0236(4) Uani 1 1 d .
O3 O 0.41138(11) 0.7551(3) 0.97222(7) 0.0239(4) Uani 1 1 d .
N1 N 0.77933(12) 1.2512(3) 0.58864(9) 0.0194(4) Uani 1 1 d .
N2 N 0.61026(12) 1.1923(3) 0.62851(8) 0.0176(4) Uani 1 1 d .
N3 N 0.49202(12) 0.9417(3) 0.60495(9) 0.0192(4) Uani 1 1 d .
N5 N 0.50075(12) 1.0141(4) 0.90742(9) 0.0195(4) Uani 1 1 d .
H5 H 0.5213 1.1125 0.9418 0.023 Uiso 1 1 calc R
N6 N 0.39075(13) 0.5187(4) 0.63613(9) 0.0207(4) Uani 1 1 d .
H6N H 0.4110(19) 0.613(5) 0.6088(14) 0.022(7) Uiso 1 1 d .
C1 C 0.77568(18) 1.1879(5) 0.51370(12) 0.0311(6) Uani 1 1 d .
H1A H 0.8329 1.1068 0.5024 0.047 Uiso 1 1 calc R
H1B H 0.7670 1.3426 0.4861 0.047 Uiso 1 1 calc R
H1C H 0.7248 1.0724 0.5028 0.047 Uiso 1 1 calc R
C2 C 0.82215(17) 1.0567(4) 0.63483(14) 0.0292(5) Uani 1 1 d .
H2A H 0.7886 0.8976 0.6286 0.044 Uiso 1 1 calc R
H2B H 0.8208 1.1116 0.6836 0.044 Uiso 1 1 calc R
H2C H 0.8854 1.0316 0.6230 0.044 Uiso 1 1 calc R
C3 C 0.54867(14) 1.1008(4) 0.57843(11) 0.0191(4) Uani 1 1 d .
H3 H 0.5473 1.1470 0.5305 0.023 Uiso 1 1 calc R
C4 C 0.59019(14) 1.0815(4) 0.69112(11) 0.0185(4) Uani 1 1 d .
H4A H 0.6214 1.1059 0.7354 0.022 Uiso 1 1 calc R
C5 C 0.51624(14) 0.9294(4) 0.67641(10) 0.0155(4) Uani 1 1 d .
C6 C 0.46377(13) 0.7854(4) 0.72618(10) 0.0149(4) Uani 1 1 d .
C7 C 0.40145(14) 0.5881(4) 0.70493(11) 0.0165(4) Uani 1 1 d .
C8 C 0.35243(13) 0.4591(4) 0.75542(11) 0.0174(4) Uani 1 1 d .
H8 H 0.3120 0.3272 0.7406 0.021 Uiso 1 1 calc R
C9 C 0.36175(13) 0.5195(4) 0.82566(11) 0.0179(4) Uani 1 1 d .
H9 H 0.3285 0.4311 0.8590 0.021 Uiso 1 1 calc R
C10 C 0.42111(13) 0.7131(4) 0.84603(10) 0.0156(4) Uani 1 1 d .
C11 C 0.44195(13) 0.8222(4) 0.91599(10) 0.0176(4) Uani 1 1 d .
C12 C 0.52683(13) 1.0422(4) 0.83597(10) 0.0157(4) Uani 1 1 d .
H12A H 0.5928 1.0116 0.8325 0.019 Uiso 1 1 calc R
H12B H 0.5116 1.2128 0.8177 0.019 Uiso 1 1 calc R
C13 C 0.47099(13) 0.8430(4) 0.79738(10) 0.0152(4) Uani 1 1 d .
C14 C 0.32378(15) 0.3352(4) 0.61131(11) 0.0217(5) Uani 1 1 d .
H14A H 0.3353 0.1744 0.6355 0.033 Uiso 1 1 calc R
H14B H 0.3279 0.3108 0.5609 0.033 Uiso 1 1 calc R
H14C H 0.2627 0.3958 0.6207 0.033 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0128(3) 0.0199(3) 0.0166(3) -0.00004(17) 0.0063(2) -0.00330(17)
O1 0.0171(8) 0.0233(8) 0.0219(8) 0.0025(6) 0.0076(6) 0.0014(6)
O2 0.0214(8) 0.0305(8) 0.0193(8) -0.0033(6) 0.0049(6) -0.0101(6)
O3 0.0212(8) 0.0349(9) 0.0168(7) -0.0001(6) 0.0101(6) -0.0081(7)
N1 0.0133(9) 0.0216(9) 0.0240(9) 0.0015(7) 0.0074(7) 0.0018(7)
N2 0.0130(8) 0.0250(9) 0.0152(8) 0.0003(6) 0.0045(6) -0.0048(7)
N3 0.0141(9) 0.0253(9) 0.0188(9) 0.0006(7) 0.0046(7) -0.0035(7)
N5 0.0159(9) 0.0279(10) 0.0155(8) -0.0037(7) 0.0084(7) -0.0065(7)
N6 0.0187(9) 0.0273(10) 0.0167(9) -0.0004(7) 0.0059(7) -0.0094(8)
C1 0.0288(13) 0.0381(13) 0.0275(12) -0.0080(10) 0.0112(9) 0.0093(10)
C2 0.0188(12) 0.0251(11) 0.0435(14) 0.0111(10) -0.0007(10) -0.0013(9)
C3 0.0147(10) 0.0270(11) 0.0160(10) -0.0005(7) 0.0044(8) -0.0036(8)
C4 0.0129(10) 0.0282(11) 0.0151(9) 0.0017(8) 0.0053(7) -0.0021(8)
C5 0.0106(9) 0.0198(9) 0.0167(9) -0.0005(7) 0.0054(7) 0.0000(7)
C6 0.0073(9) 0.0207(9) 0.0173(9) 0.0003(7) 0.0053(7) -0.0004(7)
C7 0.0104(10) 0.0204(10) 0.0190(10) -0.0015(7) 0.0040(7) 0.0008(7)
C8 0.0094(10) 0.0219(9) 0.0214(10) -0.0008(8) 0.0049(8) -0.0026(7)
C9 0.0110(10) 0.0233(10) 0.0202(10) 0.0026(8) 0.0078(7) -0.0007(8)
C10 0.0090(9) 0.0218(10) 0.0166(9) 0.0010(7) 0.0051(7) 0.0006(7)
C11 0.0104(9) 0.0260(10) 0.0169(9) -0.0011(8) 0.0047(7) -0.0004(8)
C12 0.0107(9) 0.0220(9) 0.0151(9) -0.0006(7) 0.0067(7) -0.0013(7)
C13 0.0078(9) 0.0202(9) 0.0180(9) -0.0002(7) 0.0045(7) 0.0018(7)
C14 0.0172(11) 0.0276(11) 0.0205(10) -0.0006(8) 0.0021(8) -0.0060(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 121.82(10)
O2 S1 N1 108.62(10)
O1 S1 N1 108.28(9)
O2 S1 N2 104.08(9)
O1 S1 N2 105.43(9)
N1 S1 N2 107.79(9)
C1 N1 C2 114.61(19)
C1 N1 S1 117.82(15)
C2 N1 S1 116.92(16)
C3 N2 C4 106.99(17)
C3 N2 S1 127.38(14)
C4 N2 S1 125.63(14)
C3 N3 C5 106.24(17)
C11 N5 C12 113.48(17)
C11 N5 H5 123.3
C12 N5 H5 123.3
C7 N6 C14 122.37(19)
C7 N6 H6N 116.0(19)
C14 N6 H6N 118.8(19)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N3 C3 N2 111.43(18)
N3 C3 H3 124.3
N2 C3 H3 124.3
C5 C4 N2 106.15(18)
C5 C4 H4A 126.9
N2 C4 H4A 126.9
C4 C5 N3 109.16(18)
C4 C5 C6 127.62(18)
N3 C5 C6 123.09(17)
C13 C6 C7 116.60(18)
C13 C6 C5 120.45(18)
C7 C6 C5 122.92(17)
N6 C7 C8 119.64(18)
N6 C7 C6 120.32(19)
C8 C7 C6 120.01(18)
C9 C8 C7 121.90(19)
C9 C8 H8 119.1
C7 C8 H8 119.1
C8 C9 C10 118.02(19)
C8 C9 H9 121.0
C10 C9 H9 121.0
C9 C10 C13 121.38(19)
C9 C10 C11 129.70(19)
C13 C10 C11 108.90(18)
O3 C11 N5 125.94(19)
O3 C11 C10 127.52(19)
N5 C11 C10 106.53(17)
N5 C12 C13 103.01(16)
N5 C12 H12A 111.2
C13 C12 H12A 111.2
N5 C12 H12B 111.2
C13 C12 H12B 111.2
H12A C12 H12B 109.1
C6 C13 C10 122.07(18)
C6 C13 C12 129.92(18)
C10 C13 C12 108.01(17)
N6 C14 H14A 109.5
N6 C14 H14B 109.5
H14A C14 H14B 109.5
N6 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4229(15)
S1 O1 1.4235(15)
S1 N1 1.6013(18)
S1 N2 1.6931(18)
O3 C11 1.244(3)
N1 C1 1.474(3)
N1 C2 1.476(3)
N2 C3 1.370(2)
N2 C4 1.384(3)
N3 C3 1.309(3)
N3 C5 1.397(3)
N5 C11 1.351(3)
N5 C12 1.452(3)
N5 H5 0.8800
N6 C7 1.370(3)
N6 C14 1.445(3)
N6 H6N 0.80(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 H3 0.9500
C4 C5 1.370(3)
C4 H4A 0.9500
C5 C6 1.475(3)
C6 C13 1.397(3)
C6 C7 1.434(3)
C7 C8 1.416(3)
C8 C9 1.384(3)
C8 H8 0.9500
C9 C10 1.388(3)
C9 H9 0.9500
C10 C13 1.401(3)
C10 C11 1.476(3)
C12 C13 1.505(3)
C12 H12A 0.9900
C12 H12B 0.9900
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
|
1502007.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502007.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502007
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C33 H31 N5 O3 S'
_chemical_formula_weight 577.69
_chemical_name_systematic
;
?
;
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 107.743(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 26.7452(19)
_cell_length_b 11.6338(7)
_cell_length_c 18.7886(11)
_cell_measurement_reflns_used 6996
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.24
_cell_measurement_theta_min 2.28
_cell_volume 5568.0(6)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0615
_diffrn_reflns_av_sigmaI/netI 0.0475
_diffrn_reflns_limit_h_max 35
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 18198
_diffrn_reflns_theta_full 28.27
_diffrn_reflns_theta_max 28.27
_diffrn_reflns_theta_min 1.60
_exptl_absorpt_coefficient_mu 0.162
_exptl_absorpt_correction_type none
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.378
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 2432
_exptl_crystal_size_max 0.47
_exptl_crystal_size_mid 0.33
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.520
_refine_diff_density_min -0.375
_refine_diff_density_rms 0.083
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.066
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 382
_refine_ls_number_reflns 6637
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.066
_refine_ls_R_factor_all 0.0639
_refine_ls_R_factor_gt 0.0520
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1332
_refine_ls_wR_factor_ref 0.1421
_reflns_number_gt 5228
_reflns_number_total 6637
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_003.cif
_cod_data_source_block manoj8m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M C2/c
_cod_database_code 1502007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.215136(16) 0.38527(3) 0.28240(2) 0.02335(13) Uani 1 1 d .
O1 O 0.22485(5) 0.32719(11) 0.35158(7) 0.0326(3) Uani 1 1 d .
O2 O 0.21074(5) 0.32683(10) 0.21455(7) 0.0308(3) Uani 1 1 d .
O3 O 0.13290(4) 0.86121(9) 0.53049(6) 0.0211(2) Uani 1 1 d .
N1 N 0.25632(5) 0.48961(12) 0.29219(8) 0.0231(3) Uani 1 1 d .
N2 N 0.15570(5) 0.44936(11) 0.26824(7) 0.0220(3) Uani 1 1 d .
N3 N 0.09150(5) 0.57145(12) 0.21294(7) 0.0256(3) Uani 1 1 d .
N4 N 0.09486(5) 0.88924(10) 0.40543(7) 0.0160(3) Uani 1 1 d .
N5 N 0.05793(5) 0.52846(11) 0.42534(8) 0.0202(3) Uani 1 1 d .
C1 C 0.25366(7) 0.55333(15) 0.22366(9) 0.0270(4) Uani 1 1 d .
H1A H 0.2220 0.6013 0.2095 0.040 Uiso 1 1 calc R
H1B H 0.2524 0.4989 0.1833 0.040 Uiso 1 1 calc R
H1C H 0.2848 0.6022 0.2325 0.040 Uiso 1 1 calc R
C2 C 0.26225(7) 0.56499(16) 0.35726(10) 0.0298(4) Uani 1 1 d .
H2A H 0.2961 0.6048 0.3694 0.045 Uiso 1 1 calc R
H2B H 0.2608 0.5186 0.4001 0.045 Uiso 1 1 calc R
H2C H 0.2338 0.6217 0.3455 0.045 Uiso 1 1 calc R
C3 C 0.12632(7) 0.50022(14) 0.20261(9) 0.0244(4) Uani 1 1 d .
H3 H 0.1309 0.4851 0.1553 0.029 Uiso 1 1 calc R
C4 C 0.13837(6) 0.49693(13) 0.32440(9) 0.0218(3) Uani 1 1 d .
H4 H 0.1513 0.4808 0.3764 0.026 Uiso 1 1 calc R
C5 C 0.09930(6) 0.57121(14) 0.28994(9) 0.0205(3) Uani 1 1 d .
C6 C 0.07429(6) 0.65543(13) 0.32643(8) 0.0192(3) Uani 1 1 d .
C7 C 0.06284(6) 0.76116(13) 0.29728(8) 0.0203(3) Uani 1 1 d .
H7 H 0.0636 0.7761 0.2479 0.024 Uiso 1 1 calc R
C8 C 0.04885(6) 0.85578(13) 0.34190(8) 0.0192(3) Uani 1 1 d .
H8A H 0.0362 0.9233 0.3093 0.023 Uiso 1 1 calc R
H8B H 0.0201 0.8298 0.3611 0.023 Uiso 1 1 calc R
C9 C 0.10585(6) 0.82436(13) 0.46983(8) 0.0168(3) Uani 1 1 d .
C10 C 0.08454(6) 0.70589(12) 0.46314(8) 0.0169(3) Uani 1 1 d .
C11 C 0.07973(6) 0.64255(13) 0.52533(9) 0.0203(3) Uani 1 1 d .
H11 H 0.0871 0.6697 0.5752 0.024 Uiso 1 1 calc R
C12 C 0.06256(6) 0.53563(13) 0.50012(9) 0.0208(3) Uani 1 1 d .
H12 H 0.0550 0.4755 0.5295 0.025 Uiso 1 1 calc R
C13 C 0.07154(6) 0.63291(13) 0.40179(9) 0.0179(3) Uani 1 1 d .
C14 C 0.12092(6) 1.00433(12) 0.41041(8) 0.0158(3) Uani 1 1 d .
C15 C 0.10157(6) 1.07938(12) 0.46500(8) 0.0173(3) Uani 1 1 d .
C16 C 0.13425(6) 1.13897(13) 0.52567(9) 0.0217(3) Uani 1 1 d .
H16 H 0.1712 1.1332 0.5363 0.026 Uiso 1 1 calc R
C17 C 0.11366(7) 1.20701(14) 0.57113(9) 0.0259(4) Uani 1 1 d .
H17 H 0.1367 1.2482 0.6116 0.031 Uiso 1 1 calc R
C18 C 0.05981(7) 1.21502(14) 0.55771(9) 0.0257(4) Uani 1 1 d .
H18 H 0.0457 1.2621 0.5883 0.031 Uiso 1 1 calc R
C19 C 0.02705(7) 1.15328(14) 0.49907(9) 0.0252(4) Uani 1 1 d .
H19 H -0.0099 1.1565 0.4901 0.030 Uiso 1 1 calc R
C20 C 0.04740(6) 1.08650(14) 0.45303(9) 0.0224(3) Uani 1 1 d .
H20 H 0.0242 1.0451 0.4128 0.027 Uiso 1 1 calc R
C21 C 0.18133(6) 0.99218(13) 0.43300(8) 0.0164(3) Uani 1 1 d .
C22 C 0.20711(6) 0.88671(13) 0.43810(8) 0.0187(3) Uani 1 1 d .
H22 H 0.1873 0.8176 0.4300 0.022 Uiso 1 1 calc R
C23 C 0.26169(6) 0.88143(14) 0.45502(9) 0.0226(3) Uani 1 1 d .
H23 H 0.2786 0.8091 0.4575 0.027 Uiso 1 1 calc R
C24 C 0.29125(6) 0.98145(14) 0.46819(9) 0.0232(3) Uani 1 1 d .
H24 H 0.3285 0.9777 0.4823 0.028 Uiso 1 1 calc R
C25 C 0.26607(6) 1.08702(14) 0.46066(9) 0.0229(3) Uani 1 1 d .
H25 H 0.2861 1.1559 0.4686 0.027 Uiso 1 1 calc R
C26 C 0.21162(6) 1.09230(13) 0.44149(8) 0.0190(3) Uani 1 1 d .
H26 H 0.1947 1.1651 0.4340 0.023 Uiso 1 1 calc R
C27 C 0.10604(6) 1.05630(13) 0.33097(8) 0.0183(3) Uani 1 1 d .
C28 C 0.12053(6) 0.99707(13) 0.27548(9) 0.0221(3) Uani 1 1 d .
H28 H 0.1390 0.9264 0.2876 0.026 Uiso 1 1 calc R
C29 C 0.10851(7) 1.03936(15) 0.20329(9) 0.0272(4) Uani 1 1 d .
H29 H 0.1177 0.9969 0.1659 0.033 Uiso 1 1 calc R
C30 C 0.08290(7) 1.14443(16) 0.18604(10) 0.0319(4) Uani 1 1 d .
H30 H 0.0746 1.1742 0.1367 0.038 Uiso 1 1 calc R
C31 C 0.06958(7) 1.20504(16) 0.24012(10) 0.0337(4) Uani 1 1 d .
H31 H 0.0526 1.2774 0.2283 0.040 Uiso 1 1 calc R
C32 C 0.08068(7) 1.16147(14) 0.31225(10) 0.0262(4) Uani 1 1 d .
H32 H 0.0708 1.2039 0.3491 0.031 Uiso 1 1 calc R
C33 C 0.03233(7) 0.43297(14) 0.37803(10) 0.0271(4) Uani 1 1 d .
H33A H 0.0247 0.3719 0.4091 0.041 Uiso 1 1 calc R
H33B H 0.0556 0.4031 0.3509 0.041 Uiso 1 1 calc R
H33C H -0.0005 0.4597 0.3422 0.041 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0305(2) 0.0173(2) 0.0260(2) 0.00021(15) 0.01402(18) 0.00267(15)
O1 0.0435(8) 0.0253(6) 0.0343(7) 0.0096(5) 0.0196(6) 0.0104(5)
O2 0.0418(7) 0.0225(6) 0.0337(7) -0.0069(5) 0.0198(6) -0.0017(5)
O3 0.0246(6) 0.0198(6) 0.0180(5) 0.0006(4) 0.0052(4) -0.0016(4)
N1 0.0217(7) 0.0265(7) 0.0217(7) -0.0006(6) 0.0074(6) 0.0002(5)
N2 0.0252(7) 0.0211(7) 0.0216(7) -0.0032(5) 0.0102(6) -0.0023(5)
N3 0.0269(7) 0.0291(8) 0.0199(7) -0.0050(6) 0.0057(6) -0.0024(6)
N4 0.0160(6) 0.0137(6) 0.0177(6) 0.0002(5) 0.0040(5) -0.0010(5)
N5 0.0208(7) 0.0167(6) 0.0250(7) 0.0000(5) 0.0098(5) -0.0015(5)
C1 0.0296(9) 0.0275(9) 0.0256(8) 0.0022(7) 0.0110(7) -0.0043(7)
C2 0.0291(9) 0.0344(10) 0.0237(8) -0.0059(7) 0.0049(7) -0.0025(7)
C3 0.0271(9) 0.0271(9) 0.0187(8) -0.0056(6) 0.0065(7) -0.0036(7)
C4 0.0265(9) 0.0217(8) 0.0194(8) -0.0029(6) 0.0105(7) -0.0025(6)
C5 0.0203(8) 0.0206(8) 0.0201(7) -0.0031(6) 0.0056(6) -0.0044(6)
C6 0.0166(7) 0.0205(8) 0.0189(7) -0.0033(6) 0.0032(6) -0.0033(6)
C7 0.0185(7) 0.0237(8) 0.0165(7) -0.0025(6) 0.0022(6) -0.0034(6)
C8 0.0176(7) 0.0191(8) 0.0192(7) 0.0022(6) 0.0029(6) -0.0006(6)
C9 0.0163(7) 0.0163(7) 0.0190(7) -0.0002(6) 0.0072(6) 0.0015(5)
C10 0.0146(7) 0.0163(7) 0.0210(7) 0.0012(6) 0.0071(6) 0.0016(5)
C11 0.0193(8) 0.0211(8) 0.0228(8) 0.0020(6) 0.0099(6) 0.0034(6)
C12 0.0199(8) 0.0203(8) 0.0254(8) 0.0040(6) 0.0117(7) 0.0017(6)
C13 0.0145(7) 0.0173(7) 0.0223(8) 0.0008(6) 0.0064(6) 0.0003(5)
C14 0.0169(7) 0.0131(7) 0.0183(7) 0.0013(5) 0.0068(6) 0.0005(5)
C15 0.0213(8) 0.0131(7) 0.0195(7) 0.0032(6) 0.0091(6) 0.0025(6)
C16 0.0241(8) 0.0196(8) 0.0232(8) 0.0004(6) 0.0102(6) -0.0015(6)
C17 0.0337(9) 0.0208(8) 0.0263(8) -0.0026(7) 0.0135(7) -0.0028(7)
C18 0.0365(9) 0.0185(8) 0.0291(9) 0.0020(7) 0.0205(8) 0.0040(7)
C19 0.0238(8) 0.0240(8) 0.0323(9) 0.0041(7) 0.0152(7) 0.0046(6)
C20 0.0219(8) 0.0211(8) 0.0251(8) -0.0005(6) 0.0087(7) 0.0003(6)
C21 0.0164(7) 0.0192(7) 0.0142(7) 0.0011(6) 0.0054(6) 0.0016(5)
C22 0.0199(8) 0.0184(7) 0.0181(7) 0.0019(6) 0.0063(6) 0.0013(6)
C23 0.0223(8) 0.0247(8) 0.0216(8) 0.0047(6) 0.0078(6) 0.0065(6)
C24 0.0164(7) 0.0338(9) 0.0203(8) 0.0022(7) 0.0069(6) 0.0013(6)
C25 0.0226(8) 0.0254(8) 0.0224(8) -0.0015(7) 0.0096(6) -0.0056(6)
C26 0.0211(8) 0.0179(7) 0.0201(7) 0.0000(6) 0.0093(6) -0.0005(6)
C27 0.0173(7) 0.0187(7) 0.0185(7) 0.0022(6) 0.0049(6) -0.0019(6)
C28 0.0219(8) 0.0225(8) 0.0225(8) 0.0015(6) 0.0079(7) -0.0008(6)
C29 0.0283(9) 0.0339(9) 0.0206(8) -0.0002(7) 0.0092(7) -0.0067(7)
C30 0.0329(10) 0.0373(10) 0.0226(8) 0.0122(8) 0.0043(7) -0.0063(8)
C31 0.0381(10) 0.0260(9) 0.0350(10) 0.0117(8) 0.0083(8) 0.0061(7)
C32 0.0306(9) 0.0213(8) 0.0276(9) 0.0057(7) 0.0100(7) 0.0053(7)
C33 0.0292(9) 0.0184(8) 0.0345(9) -0.0054(7) 0.0110(7) -0.0069(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 122.54(8)
O1 S1 N1 109.06(8)
O2 S1 N1 109.30(7)
O1 S1 N2 104.70(7)
O2 S1 N2 104.59(7)
N1 S1 N2 105.15(7)
C1 N1 C2 113.03(13)
C1 N1 S1 115.55(11)
C2 N1 S1 116.11(11)
C3 N2 C4 106.09(13)
C3 N2 S1 125.38(11)
C4 N2 S1 124.57(12)
C3 N3 C5 105.34(14)
C9 N4 C8 117.74(12)
C9 N4 C14 117.59(12)
C8 N4 C14 122.77(12)
C12 N5 C13 108.90(13)
C12 N5 C33 123.31(13)
C13 N5 C33 126.64(14)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N3 C3 N2 112.22(14)
N3 C3 H3 123.9
N2 C3 H3 123.9
C5 C4 N2 106.11(14)
C5 C4 H4 126.9
N2 C4 H4 126.9
C4 C5 N3 110.19(14)
C4 C5 C6 126.55(14)
N3 C5 C6 122.44(14)
C7 C6 C13 119.06(14)
C7 C6 C5 120.02(14)
C13 C6 C5 119.77(14)
C6 C7 C8 120.62(14)
C6 C7 H7 119.7
C8 C7 H7 119.7
N4 C8 C7 110.86(12)
N4 C8 H8A 109.5
C7 C8 H8A 109.5
N4 C8 H8B 109.5
C7 C8 H8B 109.5
H8A C8 H8B 108.1
O3 C9 N4 122.10(13)
O3 C9 C10 120.44(13)
N4 C9 C10 117.44(12)
C13 C10 C11 107.67(13)
C13 C10 C9 129.18(13)
C11 C10 C9 122.80(13)
C12 C11 C10 107.07(14)
C12 C11 H11 126.5
C10 C11 H11 126.5
C11 C12 N5 109.10(14)
C11 C12 H12 125.5
N5 C12 H12 125.5
N5 C13 C10 107.23(13)
N5 C13 C6 124.32(14)
C10 C13 C6 128.34(14)
N4 C14 C27 108.12(11)
N4 C14 C21 111.25(11)
C27 C14 C21 103.93(11)
N4 C14 C15 107.54(11)
C27 C14 C15 112.26(12)
C21 C14 C15 113.65(12)
C16 C15 C20 117.60(14)
C16 C15 C14 124.69(14)
C20 C15 C14 117.70(13)
C15 C16 C17 121.17(15)
C15 C16 H16 119.4
C17 C16 H16 119.4
C18 C17 C16 120.56(16)
C18 C17 H17 119.7
C16 C17 H17 119.7
C19 C18 C17 118.74(15)
C19 C18 H18 120.6
C17 C18 H18 120.6
C18 C19 C20 120.87(15)
C18 C19 H19 119.6
C20 C19 H19 119.6
C19 C20 C15 121.02(15)
C19 C20 H20 119.5
C15 C20 H20 119.5
C22 C21 C26 117.83(14)
C22 C21 C14 123.49(13)
C26 C21 C14 118.36(13)
C21 C22 C23 120.92(14)
C21 C22 H22 119.5
C23 C22 H22 119.5
C24 C23 C22 120.21(14)
C24 C23 H23 119.9
C22 C23 H23 119.9
C23 C24 C25 119.50(15)
C23 C24 H24 120.2
C25 C24 H24 120.2
C24 C25 C26 120.20(15)
C24 C25 H25 119.9
C26 C25 H25 119.9
C25 C26 C21 121.11(14)
C25 C26 H26 119.4
C21 C26 H26 119.4
C32 C27 C28 117.98(14)
C32 C27 C14 123.38(14)
C28 C27 C14 118.59(13)
C29 C28 C27 121.35(15)
C29 C28 H28 119.3
C27 C28 H28 119.3
C28 C29 C30 119.43(16)
C28 C29 H29 120.3
C30 C29 H29 120.3
C31 C30 C29 120.03(16)
C31 C30 H30 120.0
C29 C30 H30 120.0
C30 C31 C32 120.56(16)
C30 C31 H31 119.7
C32 C31 H31 119.7
C27 C32 C31 120.61(16)
C27 C32 H32 119.7
C31 C32 H32 119.7
N5 C33 H33A 109.5
N5 C33 H33B 109.5
H33A C33 H33B 109.5
N5 C33 H33C 109.5
H33A C33 H33C 109.5
H33B C33 H33C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4170(12)
S1 O2 1.4176(12)
S1 N1 1.6115(14)
S1 N2 1.7017(14)
O3 C9 1.2263(18)
N1 C1 1.468(2)
N1 C2 1.473(2)
N2 C3 1.377(2)
N2 C4 1.3901(19)
N3 C3 1.304(2)
N3 C5 1.397(2)
N4 C9 1.3796(18)
N4 C8 1.4816(19)
N4 C14 1.4992(18)
N5 C12 1.375(2)
N5 C13 1.3796(19)
N5 C33 1.457(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 H3 0.9500
C4 C5 1.359(2)
C4 H4 0.9500
C5 C6 1.469(2)
C6 C7 1.343(2)
C6 C13 1.464(2)
C7 C8 1.499(2)
C7 H7 0.9500
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.482(2)
C10 C13 1.388(2)
C10 C11 1.420(2)
C11 C12 1.360(2)
C11 H11 0.9500
C12 H12 0.9500
C14 C27 1.546(2)
C14 C21 1.547(2)
C14 C15 1.551(2)
C15 C16 1.392(2)
C15 C20 1.399(2)
C16 C17 1.395(2)
C16 H16 0.9500
C17 C18 1.388(2)
C17 H17 0.9500
C18 C19 1.382(2)
C18 H18 0.9500
C19 C20 1.391(2)
C19 H19 0.9500
C20 H20 0.9500
C21 C22 1.396(2)
C21 C26 1.400(2)
C22 C23 1.397(2)
C22 H22 0.9500
C23 C24 1.386(2)
C23 H23 0.9500
C24 C25 1.387(2)
C24 H24 0.9500
C25 C26 1.391(2)
C25 H25 0.9500
C26 H26 0.9500
C27 C32 1.391(2)
C27 C28 1.399(2)
C28 C29 1.385(2)
C28 H28 0.9500
C29 C30 1.390(3)
C29 H29 0.9500
C30 C31 1.370(3)
C30 H30 0.9500
C31 C32 1.392(2)
C31 H31 0.9500
C32 H32 0.9500
C33 H33A 0.9800
C33 H33B 0.9800
C33 H33C 0.9800
|
1502008.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502008.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502008
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C15 H19 N5 O3 S'
_chemical_formula_weight 349.41
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 91.7830(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 11.9670(13)
_cell_length_b 12.7826(14)
_cell_length_c 10.6078(11)
_cell_measurement_reflns_used 3521
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 27.36
_cell_measurement_theta_min 2.50
_cell_volume 1621.9(3)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0412
_diffrn_reflns_av_sigmaI/netI 0.0468
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 10625
_diffrn_reflns_theta_full 28.29
_diffrn_reflns_theta_max 28.29
_diffrn_reflns_theta_min 1.70
_exptl_absorpt_coefficient_mu 0.225
_exptl_absorpt_correction_type none
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.431
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 736
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.652
_refine_diff_density_min -0.302
_refine_diff_density_rms 0.074
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 221
_refine_ls_number_reflns 3907
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.026
_refine_ls_R_factor_all 0.0671
_refine_ls_R_factor_gt 0.0522
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1351
_refine_ls_wR_factor_ref 0.1444
_reflns_number_gt 2925
_reflns_number_total 3907
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_004.cif
_cod_data_source_block manoj13m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.00287(4) 0.88808(4) 0.23448(5) 0.02815(17) Uani 1 1 d .
O1 O -0.08191(11) 0.92397(12) 0.31495(15) 0.0393(4) Uani 1 1 d .
O2 O -0.01560(12) 0.80664(10) 0.14525(15) 0.0374(4) Uani 1 1 d .
O3 O 0.67475(12) 0.64789(13) 0.26405(15) 0.0423(4) Uani 1 1 d .
C1 C 0.06271(18) 1.08635(16) 0.2315(2) 0.0386(5) Uani 1 1 d .
H1A H 0.1271 1.0835 0.2907 0.058 Uiso 1 1 calc R
H1B H -0.0055 1.0982 0.2782 0.058 Uiso 1 1 calc R
H1C H 0.0728 1.1437 0.1717 0.058 Uiso 1 1 calc R
C2 C 0.14482(17) 0.96670(16) 0.07529(19) 0.0321(5) Uani 1 1 d .
H2A H 0.1524 1.0266 0.0186 0.048 Uiso 1 1 calc R
H2B H 0.1279 0.9037 0.0256 0.048 Uiso 1 1 calc R
H2C H 0.2149 0.9565 0.1240 0.048 Uiso 1 1 calc R
C3 C 0.11986(18) 0.87024(17) 0.4593(2) 0.0352(5) Uani 1 1 d .
H3 H 0.0728 0.9174 0.5021 0.042 Uiso 1 1 calc R
C4 C 0.19001(15) 0.77364(14) 0.30690(18) 0.0231(4) Uani 1 1 d .
H4 H 0.2029 0.7409 0.2283 0.028 Uiso 1 1 calc R
C5 C 0.25239(15) 0.76403(14) 0.41649(17) 0.0228(4) Uani 1 1 d .
C6 C 0.35743(16) 0.70547(13) 0.43999(17) 0.0230(4) Uani 1 1 d .
C7 C 0.42729(15) 0.73039(14) 0.53719(17) 0.0238(4) Uani 1 1 d .
H7 H 0.4079 0.7851 0.5931 0.029 Uiso 1 1 calc R
C8 C 0.53522(16) 0.67292(15) 0.55827(18) 0.0279(4) Uani 1 1 d .
H8A H 0.5699 0.6950 0.6400 0.033 Uiso 1 1 calc R
H8B H 0.5198 0.5970 0.5632 0.033 Uiso 1 1 calc R
C9 C 0.60043(17) 0.64579(15) 0.34310(19) 0.0303(5) Uani 1 1 d .
C10 C 0.49179(16) 0.59611(15) 0.31503(18) 0.0278(4) Uani 1 1 d .
C11 C 0.37003(18) 0.49483(15) 0.20744(19) 0.0336(5) Uani 1 1 d .
H11 H 0.3404 0.4429 0.1517 0.040 Uiso 1 1 calc R
C12 C 0.30833(17) 0.55697(14) 0.28291(18) 0.0291(4) Uani 1 1 d .
H12 H 0.2293 0.5566 0.2885 0.035 Uiso 1 1 calc R
C13 C 0.38440(16) 0.62247(14) 0.35174(18) 0.0245(4) Uani 1 1 d .
C14 C 0.71792(17) 0.74816(18) 0.4894(2) 0.0387(5) Uani 1 1 d .
H14A H 0.7671 0.7034 0.5415 0.058 Uiso 1 1 calc R
H14B H 0.7007 0.8120 0.5361 0.058 Uiso 1 1 calc R
H14C H 0.7554 0.7666 0.4116 0.058 Uiso 1 1 calc R
C15 C 0.5695(2) 0.46019(19) 0.1648(2) 0.0472(6) Uani 1 1 d .
H15A H 0.5368 0.4071 0.1082 0.071 Uiso 1 1 calc R
H15B H 0.6164 0.4260 0.2301 0.071 Uiso 1 1 calc R
H15C H 0.6153 0.5084 0.1164 0.071 Uiso 1 1 calc R
N1 N 0.05330(13) 0.98662(12) 0.16226(15) 0.0266(4) Uani 1 1 d .
N2 N 0.10366(13) 0.84164(13) 0.33508(15) 0.0264(4) Uani 1 1 d .
N3 N 0.20698(15) 0.82528(14) 0.51099(16) 0.0330(4) Uani 1 1 d .
N4 N 0.61401(13) 0.69199(12) 0.45786(16) 0.0293(4) Uani 1 1 d .
N5 N 0.48063(15) 0.51821(13) 0.22376(16) 0.0321(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0222(3) 0.0266(3) 0.0353(3) 0.0048(2) -0.0056(2) -0.00040(19)
O1 0.0236(7) 0.0438(9) 0.0510(10) 0.0114(7) 0.0073(7) 0.0050(6)
O2 0.0361(9) 0.0260(7) 0.0489(10) 0.0025(6) -0.0195(7) -0.0035(6)
O3 0.0301(8) 0.0598(10) 0.0372(9) 0.0017(8) 0.0041(7) 0.0118(7)
C1 0.0357(12) 0.0276(11) 0.0528(15) -0.0106(10) 0.0077(10) -0.0024(9)
C2 0.0366(11) 0.0330(11) 0.0269(11) 0.0019(8) 0.0021(9) 0.0021(9)
C3 0.0369(12) 0.0427(12) 0.0261(11) -0.0023(9) 0.0037(9) 0.0122(9)
C4 0.0255(10) 0.0196(8) 0.0241(10) 0.0009(7) -0.0008(7) -0.0021(7)
C5 0.0262(10) 0.0207(9) 0.0215(9) 0.0024(7) -0.0003(7) -0.0032(7)
C6 0.0291(10) 0.0197(9) 0.0200(9) 0.0032(7) -0.0017(7) -0.0024(7)
C7 0.0299(10) 0.0205(9) 0.0210(9) 0.0010(7) -0.0014(7) -0.0012(7)
C8 0.0338(11) 0.0281(10) 0.0211(10) 0.0011(8) -0.0089(8) 0.0012(8)
C9 0.0294(11) 0.0316(11) 0.0297(11) 0.0062(8) -0.0011(8) 0.0130(8)
C10 0.0376(11) 0.0257(10) 0.0195(10) 0.0000(7) -0.0061(8) 0.0066(8)
C11 0.0469(13) 0.0250(10) 0.0280(11) -0.0006(8) -0.0136(9) 0.0051(9)
C12 0.0354(11) 0.0250(10) 0.0265(10) 0.0017(8) -0.0070(8) 0.0038(8)
C13 0.0299(10) 0.0220(9) 0.0214(9) 0.0034(7) -0.0050(8) 0.0031(7)
C14 0.0285(11) 0.0384(12) 0.0487(14) 0.0001(10) -0.0057(9) 0.0058(9)
C15 0.0567(15) 0.0447(13) 0.0402(14) -0.0124(11) 0.0001(11) 0.0230(11)
N1 0.0281(9) 0.0220(8) 0.0297(9) 0.0009(6) -0.0007(7) -0.0007(6)
N2 0.0243(8) 0.0300(8) 0.0249(8) 0.0030(7) -0.0010(6) 0.0033(7)
N3 0.0384(10) 0.0391(10) 0.0214(9) 0.0004(7) 0.0001(7) 0.0070(8)
N4 0.0249(9) 0.0322(9) 0.0304(9) 0.0000(7) -0.0034(7) 0.0045(7)
N5 0.0412(10) 0.0268(9) 0.0280(9) -0.0020(7) -0.0041(7) 0.0131(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 122.52(9)
O2 S1 N1 108.11(9)
O1 S1 N1 108.65(9)
O2 S1 N2 104.85(8)
O1 S1 N2 104.02(9)
N1 S1 N2 107.79(8)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N3 C3 N2 112.02(18)
N3 C3 H3 124.0
N2 C3 H3 124.0
C5 C4 N2 105.26(16)
C5 C4 H4 127.4
N2 C4 H4 127.4
C4 C5 N3 110.23(16)
C4 C5 C6 128.91(17)
N3 C5 C6 120.75(16)
C7 C6 C13 121.32(17)
C7 C6 C5 120.96(17)
C13 C6 C5 117.68(15)
C6 C7 C8 120.74(17)
C6 C7 H7 119.6
C8 C7 H7 119.6
N4 C8 C7 112.44(15)
N4 C8 H8A 109.1
C7 C8 H8A 109.1
N4 C8 H8B 109.1
C7 C8 H8B 109.1
H8A C8 H8B 107.8
O3 C9 N4 121.85(19)
O3 C9 C10 121.37(19)
N4 C9 C10 116.75(18)
N5 C10 C13 107.31(17)
N5 C10 C9 121.01(18)
C13 C10 C9 130.98(18)
C12 C11 N5 109.86(18)
C12 C11 H11 125.1
N5 C11 H11 125.1
C11 C12 C13 107.17(18)
C11 C12 H12 126.4
C13 C12 H12 126.4
C10 C13 C12 107.15(17)
C10 C13 C6 125.39(17)
C12 C13 C6 127.40(18)
N4 C14 H14A 109.5
N4 C14 H14B 109.5
H14A C14 H14B 109.5
N4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N5 C15 H15A 109.5
N5 C15 H15B 109.5
H15A C15 H15B 109.5
N5 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 N1 C2 114.47(16)
C1 N1 S1 117.76(14)
C2 N1 S1 117.46(13)
C3 N2 C4 106.78(15)
C3 N2 S1 125.96(14)
C4 N2 S1 127.13(13)
C3 N3 C5 105.70(17)
C9 N4 C8 121.17(16)
C9 N4 C14 119.64(18)
C8 N4 C14 118.46(17)
C11 N5 C10 108.48(17)
C11 N5 C15 123.66(18)
C10 N5 C15 127.45(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4197(15)
S1 O1 1.4221(16)
S1 N1 1.6021(16)
S1 N2 1.6928(16)
O3 C9 1.242(2)
C1 N1 1.474(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 N1 1.476(3)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 N3 1.297(3)
C3 N2 1.375(3)
C3 H3 0.9500
C4 C5 1.367(2)
C4 N2 1.390(2)
C4 H4 0.9500
C5 N3 1.395(2)
C5 C6 1.477(3)
C6 C7 1.345(2)
C6 C13 1.458(3)
C7 C8 1.497(3)
C7 H7 0.9500
C8 N4 1.465(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 N4 1.358(3)
C9 C10 1.469(3)
C10 N5 1.392(2)
C10 C13 1.396(3)
C11 C12 1.361(3)
C11 N5 1.363(3)
C11 H11 0.9500
C12 C13 1.422(3)
C12 H12 0.9500
C14 N4 1.465(3)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 N5 1.454(3)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
|
1502009.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502009.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502009
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C13 H15 N5 O3 S'
_chemical_formula_weight 321.36
_chemical_name_systematic
;
?
;
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 94.238(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 35.609(3)
_cell_length_b 5.7753(5)
_cell_length_c 14.2217(13)
_cell_measurement_reflns_used 2655
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 28.05
_cell_measurement_theta_min 2.29
_cell_volume 2916.7(4)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0989
_diffrn_reflns_av_sigmaI/netI 0.0633
_diffrn_reflns_limit_h_max 47
_diffrn_reflns_limit_h_min -35
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 9277
_diffrn_reflns_theta_full 28.30
_diffrn_reflns_theta_max 28.30
_diffrn_reflns_theta_min 1.15
_exptl_absorpt_coefficient_mu 0.243
_exptl_absorpt_correction_type none
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.464
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 1344
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.328
_refine_diff_density_min -0.321
_refine_diff_density_rms 0.076
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.138
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 3508
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.138
_refine_ls_R_factor_all 0.0681
_refine_ls_R_factor_gt 0.0587
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1589
_refine_ls_wR_factor_ref 0.1666
_reflns_number_gt 2749
_reflns_number_total 3508
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_005.cif
_cod_data_source_block manoj3m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2916.8(5)
_cod_original_sg_symbol_H-M C2/c
_cod_database_code 1502009
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.034239(13) 0.56840(8) 0.38771(3) 0.04456(19) Uani 1 1 d .
O1 O 0.00442(4) 0.7235(3) 0.36374(10) 0.0614(4) Uani 1 1 d .
O2 O 0.03147(5) 0.3272(3) 0.37140(12) 0.0687(5) Uani 1 1 d .
O3 O 0.22527(4) 0.4730(3) -0.08209(9) 0.0545(4) Uani 1 1 d .
N1 N 0.04844(5) 0.6065(3) 0.49510(11) 0.0502(4) Uani 1 1 d .
N2 N 0.06960(4) 0.6555(3) 0.32184(10) 0.0440(4) Uani 1 1 d .
N3 N 0.10570(5) 0.8870(3) 0.24296(11) 0.0490(4) Uani 1 1 d .
N4 N 0.17503(4) 0.7924(3) 0.08733(9) 0.0402(3) Uani 1 1 d .
N5 N 0.22802(4) 0.4436(3) 0.07738(11) 0.0465(4) Uani 1 1 d .
H5 H 0.2390 0.3111 0.0769 0.056 Uiso 1 1 calc R
C1 C 0.07624(8) 0.4499(4) 0.5409(2) 0.0743(7) Uani 1 1 d .
H1A H 0.1010 0.5144 0.5377 0.111 Uiso 1 1 calc R
H1B H 0.0750 0.3028 0.5094 0.111 Uiso 1 1 calc R
H1C H 0.0711 0.4296 0.6057 0.111 Uiso 1 1 calc R
C2 C 0.04845(7) 0.8428(5) 0.53264(18) 0.0694(6) Uani 1 1 d .
H2A H 0.0390 0.8414 0.5942 0.104 Uiso 1 1 calc R
H2B H 0.0327 0.9392 0.4914 0.104 Uiso 1 1 calc R
H2C H 0.0737 0.9026 0.5369 0.104 Uiso 1 1 calc R
C3 C 0.07344(6) 0.8671(3) 0.27965(13) 0.0471(4) Uani 1 1 d .
H3 H 0.0552 0.9824 0.2775 0.057 Uiso 1 1 calc R
C4 C 0.10255(5) 0.5370(3) 0.31104(13) 0.0454(4) Uani 1 1 d .
H4 H 0.1086 0.3888 0.3329 0.054 Uiso 1 1 calc R
C5 C 0.12451(5) 0.6788(3) 0.26233(11) 0.0404(4) Uani 1 1 d .
C6 C 0.16263(5) 0.6153(3) 0.24063(12) 0.0453(4) Uani 1 1 d .
H6 H 0.1749 0.5245 0.2874 0.054 Uiso 1 1 calc R
C7 C 0.18401(5) 0.6581(3) 0.16869(11) 0.0416(4) Uani 1 1 d .
C8 C 0.22281(5) 0.5569(4) 0.16749(12) 0.0507(5) Uani 1 1 d .
H8A H 0.2414 0.6789 0.1781 0.061 Uiso 1 1 calc R
H8B H 0.2267 0.4451 0.2182 0.061 Uiso 1 1 calc R
C9 C 0.21588(5) 0.5436(3) -0.00483(12) 0.0421(4) Uani 1 1 d .
C10 C 0.19036(5) 0.7397(3) 0.00254(11) 0.0412(4) Uani 1 1 d .
C11 C 0.17663(5) 0.8955(3) -0.06327(13) 0.0491(5) Uani 1 1 d .
H11 H 0.1820 0.9001 -0.1262 0.059 Uiso 1 1 calc R
C12 C 0.15278(6) 1.0481(4) -0.01857(15) 0.0538(5) Uani 1 1 d .
H12 H 0.1397 1.1723 -0.0468 0.065 Uiso 1 1 calc R
C13 C 0.15216(6) 0.9822(3) 0.07348(13) 0.0492(5) Uani 1 1 d .
H13 H 0.1386 1.0535 0.1188 0.059 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0421(3) 0.0466(3) 0.0462(3) 0.00019(17) 0.0114(2) -0.00210(17)
O1 0.0456(8) 0.0828(11) 0.0567(8) 0.0114(7) 0.0095(6) 0.0105(7)
O2 0.0714(10) 0.0526(9) 0.0857(11) -0.0159(8) 0.0287(8) -0.0173(8)
O3 0.0574(9) 0.0684(9) 0.0382(7) -0.0060(6) 0.0079(6) 0.0111(7)
N1 0.0527(10) 0.0555(9) 0.0433(8) 0.0078(7) 0.0094(7) 0.0012(7)
N2 0.0443(8) 0.0465(8) 0.0427(8) 0.0027(6) 0.0127(6) 0.0028(7)
N3 0.0524(9) 0.0514(9) 0.0450(8) 0.0071(6) 0.0165(7) 0.0074(7)
N4 0.0370(7) 0.0475(8) 0.0366(7) 0.0041(6) 0.0061(6) 0.0025(6)
N5 0.0408(8) 0.0584(10) 0.0407(8) 0.0005(6) 0.0063(6) 0.0116(7)
C1 0.0696(16) 0.0750(16) 0.0768(16) 0.0314(13) -0.0050(13) -0.0003(12)
C2 0.0627(14) 0.0744(15) 0.0719(14) -0.0212(12) 0.0101(11) -0.0077(12)
C3 0.0524(11) 0.0484(10) 0.0419(9) 0.0063(7) 0.0135(8) 0.0106(8)
C4 0.0496(10) 0.0458(10) 0.0418(9) 0.0027(7) 0.0102(7) 0.0075(8)
C5 0.0451(10) 0.0477(10) 0.0286(7) -0.0018(6) 0.0053(6) 0.0053(7)
C6 0.0440(10) 0.0574(11) 0.0347(8) 0.0048(7) 0.0049(7) 0.0095(8)
C7 0.0392(9) 0.0517(10) 0.0340(8) 0.0017(7) 0.0041(7) 0.0057(8)
C8 0.0407(10) 0.0761(14) 0.0353(9) 0.0010(8) 0.0035(7) 0.0117(8)
C9 0.0367(9) 0.0532(10) 0.0366(8) -0.0026(7) 0.0042(7) -0.0027(7)
C10 0.0375(9) 0.0527(10) 0.0339(8) 0.0015(7) 0.0058(6) -0.0018(7)
C11 0.0488(11) 0.0594(12) 0.0399(9) 0.0083(8) 0.0082(8) 0.0012(8)
C12 0.0543(12) 0.0566(12) 0.0517(11) 0.0177(8) 0.0124(9) 0.0125(9)
C13 0.0491(10) 0.0524(10) 0.0476(10) 0.0074(8) 0.0124(8) 0.0095(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 122.91(11)
O1 S1 N1 108.95(9)
O2 S1 N1 107.91(10)
O1 S1 N2 104.70(8)
O2 S1 N2 104.26(9)
N1 S1 N2 107.03(8)
C1 N1 C2 115.64(18)
C1 N1 S1 120.08(17)
C2 N1 S1 118.08(15)
C3 N2 C4 106.29(15)
C3 N2 S1 127.29(13)
C4 N2 S1 125.92(13)
C3 N3 C5 105.68(15)
C13 N4 C10 108.46(14)
C13 N4 C7 130.84(15)
C10 N4 C7 120.71(15)
C9 N5 C8 121.05(16)
C9 N5 H5 119.5
C8 N5 H5 119.5
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N3 C3 N2 111.91(16)
N3 C3 H3 124.0
N2 C3 H3 124.0
C5 C4 N2 106.58(16)
C5 C4 H4 126.7
N2 C4 H4 126.7
C4 C5 N3 109.53(16)
C4 C5 C6 122.42(17)
N3 C5 C6 127.96(17)
C7 C6 C5 134.67(16)
C7 C6 H6 112.7
C5 C6 H6 112.7
C6 C7 N4 128.28(16)
C6 C7 C8 120.74(16)
N4 C7 C8 110.97(15)
N5 C8 C7 111.13(14)
N5 C8 H8A 109.4
C7 C8 H8A 109.4
N5 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
O3 C9 N5 122.56(17)
O3 C9 C10 121.86(16)
N5 C9 C10 115.58(15)
C11 C10 N4 107.87(15)
C11 C10 C9 131.00(16)
N4 C10 C9 121.12(15)
C10 C11 C12 107.52(16)
C10 C11 H11 126.2
C12 C11 H11 126.2
C13 C12 C11 108.13(17)
C13 C12 H12 125.9
C11 C12 H12 125.9
C12 C13 N4 108.02(17)
C12 C13 H13 126.0
N4 C13 H13 126.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4117(15)
S1 O2 1.4146(16)
S1 N1 1.5881(17)
S1 N2 1.7001(15)
O3 C9 1.241(2)
N1 C1 1.458(3)
N1 C2 1.466(3)
N2 C3 1.373(3)
N2 C4 1.376(2)
N3 C3 1.301(3)
N3 C5 1.394(2)
N4 C13 1.371(2)
N4 C10 1.393(2)
N4 C7 1.410(2)
N5 C9 1.346(2)
N5 C8 1.463(2)
N5 H5 0.8600
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 H3 0.9300
C4 C5 1.357(3)
C4 H4 0.9300
C5 C6 1.461(3)
C6 C7 1.343(3)
C6 H6 0.9300
C7 C8 1.501(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.461(3)
C10 C11 1.362(2)
C11 C12 1.408(3)
C11 H11 0.9300
C12 C13 1.365(3)
C12 H12 0.9300
C13 H13 0.9300
|
1502010.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502010.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502010
loop_
_publ_author_name
'Bhandari, Manojkumar R.'
'Yousufuddin, Muhammed'
'Lovely, Carl J.'
_publ_section_title
;
Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1382
_journal_page_last 1385
_journal_paper_doi 10.1021/ol200067e
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C36 H38 N5 O3 S'
_chemical_formula_weight 620.77
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 68.844(2)
_cell_angle_beta 89.865(2)
_cell_angle_gamma 85.494(2)
_cell_formula_units_Z 2
_cell_length_a 9.6362(9)
_cell_length_b 11.6135(11)
_cell_length_c 14.9611(14)
_cell_measurement_reflns_used 3888
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 28.16
_cell_measurement_theta_min 2.54
_cell_volume 1556.0(3)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0537
_diffrn_reflns_av_sigmaI/netI 0.0633
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 10368
_diffrn_reflns_theta_full 28.29
_diffrn_reflns_theta_max 28.29
_diffrn_reflns_theta_min 1.46
_exptl_absorpt_coefficient_mu 0.150
_exptl_absorpt_correction_type none
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.325
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 658
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.02
_refine_diff_density_max 2.512
_refine_diff_density_min -0.826
_refine_diff_density_rms 0.126
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.717
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 410
_refine_ls_number_reflns 7169
_refine_ls_number_restraints 18
_refine_ls_restrained_S_all 1.730
_refine_ls_R_factor_all 0.1086
_refine_ls_R_factor_gt 0.0862
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.2631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2144
_refine_ls_wR_factor_ref 0.2308
_reflns_number_gt 5258
_reflns_number_total 7169
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200067e_si_007.cif
_cod_data_source_block manoj6m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502010
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75920(10) 0.50247(9) 0.09841(6) 0.0243(2) Uani 1 1 d . . .
O1 O 0.8444(3) 0.5040(3) 0.02046(19) 0.0333(7) Uani 1 1 d . . .
O2 O 0.6199(3) 0.4680(3) 0.1049(2) 0.0321(6) Uani 1 1 d . . .
O3 O 0.5019(2) 0.1964(2) 0.68319(17) 0.0240(6) Uani 1 1 d . . .
N1 N 0.7602(3) 0.6322(3) 0.1128(2) 0.0249(7) Uani 1 1 d . . .
N2 N 0.8456(3) 0.3940(3) 0.1948(2) 0.0254(7) Uani 1 1 d . . .
N3 N 1.0105(3) 0.2593(3) 0.2839(2) 0.0319(8) Uani 1 1 d . . .
N4 N 0.5605(3) 0.1660(3) 0.3879(2) 0.0254(7) Uani 1 1 d . . .
N5 N 0.7239(3) 0.1350(3) 0.65317(19) 0.0187(6) Uani 1 1 d . . .
C1 C 0.8964(4) 0.6848(4) 0.1070(3) 0.0382(10) Uani 1 1 d . . .
H1A H 0.8816 0.7749 0.0890 0.057 Uiso 1 1 calc R . .
H1B H 0.9524 0.6657 0.0586 0.057 Uiso 1 1 calc R . .
H1C H 0.9454 0.6488 0.1694 0.057 Uiso 1 1 calc R . .
C2 C 0.6615(4) 0.6598(4) 0.1787(3) 0.0322(9) Uani 1 1 d . . .
H2A H 0.6981 0.6196 0.2447 0.048 Uiso 1 1 calc R . .
H2B H 0.5718 0.6285 0.1726 0.048 Uiso 1 1 calc R . .
H2C H 0.6487 0.7496 0.1628 0.048 Uiso 1 1 calc R . .
C3 C 0.9794(4) 0.3427(4) 0.1998(3) 0.0311(9) Uani 1 1 d . . .
H3 H 1.0419 0.3652 0.1483 0.037 Uiso 1 1 calc R . .
C4 C 0.7900(4) 0.3388(3) 0.2843(3) 0.0258(8) Uani 1 1 d . . .
H4 H 0.6992 0.3554 0.3040 0.031 Uiso 1 1 calc R . .
C5 C 0.8936(4) 0.2552(3) 0.3385(3) 0.0239(8) Uani 1 1 d . . .
C6 C 0.8929(4) 0.1713(4) 0.4382(3) 0.0250(8) Uani 1 1 d . . .
H6 H 0.9818 0.1403 0.4682 0.030 Uiso 1 1 calc R . .
C7 C 0.7831(4) 0.1318(3) 0.4935(2) 0.0216(7) Uani 1 1 d . . .
C8 C 0.6348(4) 0.1566(3) 0.4687(2) 0.0219(7) Uani 1 1 d . . .
C9 C 0.4212(4) 0.1945(4) 0.4010(3) 0.0281(8) Uani 1 1 d . . .
H9 H 0.3477 0.2069 0.3554 0.034 Uiso 1 1 calc R . .
C10 C 0.4062(4) 0.2021(4) 0.4893(3) 0.0275(8) Uani 1 1 d . . .
H10 H 0.3219 0.2209 0.5161 0.033 Uiso 1 1 calc R . .
C11 C 0.5410(4) 0.1764(3) 0.5336(2) 0.0223(7) Uani 1 1 d . . .
C12 C 0.5844(4) 0.1705(3) 0.6295(2) 0.0204(7) Uani 1 1 d . . .
C13 C 0.8002(4) 0.0637(3) 0.6002(2) 0.0210(7) Uani 1 1 d . . .
H13A H 0.7639 -0.0188 0.6176 0.025 Uiso 1 1 calc R . .
H13B H 0.9004 0.0512 0.6188 0.025 Uiso 1 1 calc R . .
C14 C 0.6098(5) 0.1221(4) 0.3128(3) 0.0313(9) Uani 1 1 d . . .
H14A H 0.7057 0.0850 0.3283 0.047 Uiso 1 1 calc R . .
H14B H 0.6067 0.1919 0.2514 0.047 Uiso 1 1 calc R . .
H14C H 0.5500 0.0598 0.3082 0.047 Uiso 1 1 calc R . .
C15 C 0.7703(3) 0.1076(3) 0.7556(2) 0.0174(7) Uani 1 1 d . . .
C16 C 0.9310(4) 0.0888(3) 0.7640(2) 0.0194(7) Uani 1 1 d . . .
C17 C 1.0013(4) -0.0045(3) 0.8400(3) 0.0234(8) Uani 1 1 d . . .
H17 H 0.9505 -0.0631 0.8870 0.028 Uiso 1 1 calc R . .
C18 C 1.1468(4) -0.0129(4) 0.8476(3) 0.0278(8) Uani 1 1 d . . .
H18 H 1.1941 -0.0777 0.8995 0.033 Uiso 1 1 calc R . .
C19 C 1.2218(4) 0.0719(4) 0.7808(3) 0.0263(8) Uani 1 1 d . . .
H19 H 1.3206 0.0653 0.7858 0.032 Uiso 1 1 calc R . .
C20 C 1.1515(4) 0.1675(4) 0.7056(3) 0.0269(8) Uani 1 1 d . . .
H20 H 1.2027 0.2272 0.6598 0.032 Uiso 1 1 calc R . .
C21 C 1.0081(4) 0.1762(3) 0.6973(3) 0.0238(8) Uani 1 1 d . . .
H21 H 0.9613 0.2421 0.6459 0.029 Uiso 1 1 calc R . .
C22 C 0.6982(3) -0.0067(3) 0.8181(2) 0.0181(7) Uani 1 1 d . . .
C23 C 0.5850(3) 0.0002(3) 0.8744(2) 0.0185(7) Uani 1 1 d . . .
H23 H 0.5527 0.0778 0.8779 0.022 Uiso 1 1 calc R . .
C24 C 0.5185(4) -0.1050(3) 0.9258(2) 0.0221(7) Uani 1 1 d . . .
H24 H 0.4421 -0.0983 0.9644 0.027 Uiso 1 1 calc R . .
C25 C 0.5619(4) -0.2188(3) 0.9213(3) 0.0235(8) Uani 1 1 d . . .
H25 H 0.5163 -0.2904 0.9566 0.028 Uiso 1 1 calc R . .
C26 C 0.6730(4) -0.2268(3) 0.8646(3) 0.0240(8) Uani 1 1 d . . .
H26 H 0.7027 -0.3044 0.8601 0.029 Uiso 1 1 calc R . .
C27 C 0.7416(4) -0.1231(3) 0.8141(2) 0.0210(7) Uani 1 1 d . . .
H27 H 0.8188 -0.1309 0.7765 0.025 Uiso 1 1 calc R . .
C28 C 0.7404(3) 0.2225(3) 0.7838(3) 0.0203(7) Uani 1 1 d . . .
C29 C 0.7146(4) 0.3419(3) 0.7162(3) 0.0277(8) Uani 1 1 d . . .
H29 H 0.7065 0.3539 0.6501 0.033 Uiso 1 1 calc R . .
C30 C 0.7005(5) 0.4440(4) 0.7450(3) 0.0354(10) Uani 1 1 d . . .
H30 H 0.6822 0.5250 0.6984 0.043 Uiso 1 1 calc R . .
C31 C 0.7128(4) 0.4282(4) 0.8404(3) 0.0329(9) Uani 1 1 d . . .
H31 H 0.7011 0.4979 0.8596 0.040 Uiso 1 1 calc R . .
C32 C 0.7424(4) 0.3104(4) 0.9086(3) 0.0278(8) Uani 1 1 d . . .
H32 H 0.7530 0.2994 0.9744 0.033 Uiso 1 1 calc R . .
C33 C 0.7565(3) 0.2085(3) 0.8801(3) 0.0217(7) Uani 1 1 d . . .
H33 H 0.7774 0.1281 0.9269 0.026 Uiso 1 1 calc R . .
C34 C 0.8889(9) 0.4924(9) 0.4680(7) 0.112(3) Uani 1 1 d U A 1
H34A H 0.9122 0.5333 0.5123 0.168 Uiso 1 1 calc R A 1
H34B H 0.9294 0.5343 0.4056 0.168 Uiso 1 1 calc R A 1
H34C H 0.9265 0.4056 0.4939 0.168 Uiso 1 1 calc R A 1
C35 C 0.7508(5) 0.4980(4) 0.4575(3) 0.0349(9) Uani 1 1 d U A 1
H35A H 0.7559 0.4394 0.4229 0.042 Uiso 1 1 calc R A 1
H35B H 0.7464 0.5799 0.4049 0.042 Uiso 1 1 calc R A 1
C36 C 0.5484(5) 0.4996(5) 0.4662(4) 0.0482(12) Uani 1 1 d U . 1
H36A H 0.5153 0.5725 0.4095 0.058 Uiso 1 1 calc R . 1
H36B H 0.5275 0.4269 0.4504 0.058 Uiso 1 1 calc R . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0290(5) 0.0236(5) 0.0202(4) -0.0080(4) -0.0022(3) -0.0001(4)
O1 0.0459(17) 0.0321(16) 0.0208(14) -0.0097(12) 0.0025(12) 0.0030(13)
O2 0.0329(15) 0.0300(15) 0.0343(15) -0.0125(12) -0.0066(12) -0.0038(12)
O3 0.0199(13) 0.0309(14) 0.0219(13) -0.0108(11) 0.0031(10) 0.0000(10)
N1 0.0245(16) 0.0234(16) 0.0270(16) -0.0095(13) 0.0003(13) -0.0006(12)
N2 0.0284(17) 0.0258(17) 0.0206(15) -0.0076(13) 0.0021(13) 0.0027(13)
N3 0.0301(18) 0.0348(19) 0.0248(17) -0.0051(15) 0.0074(14) 0.0062(14)
N4 0.0324(18) 0.0256(17) 0.0189(15) -0.0088(13) -0.0014(13) -0.0037(13)
N5 0.0229(15) 0.0203(15) 0.0139(13) -0.0073(11) 0.0020(11) -0.0016(11)
C1 0.035(2) 0.037(2) 0.048(3) -0.020(2) 0.010(2) -0.0138(18)
C2 0.031(2) 0.030(2) 0.040(2) -0.0186(19) 0.0035(17) -0.0007(17)
C3 0.026(2) 0.038(2) 0.025(2) -0.0085(17) 0.0073(15) 0.0063(17)
C4 0.028(2) 0.026(2) 0.0229(18) -0.0088(15) 0.0066(15) -0.0009(15)
C5 0.0260(19) 0.0243(19) 0.0221(18) -0.0100(15) 0.0041(14) 0.0014(14)
C6 0.0263(19) 0.028(2) 0.0206(18) -0.0108(15) -0.0011(14) 0.0056(15)
C7 0.0290(19) 0.0191(17) 0.0182(17) -0.0091(14) 0.0006(14) 0.0006(14)
C8 0.0281(19) 0.0191(18) 0.0181(17) -0.0060(14) -0.0009(14) -0.0033(14)
C9 0.030(2) 0.029(2) 0.0248(19) -0.0087(16) -0.0037(15) -0.0053(16)
C10 0.028(2) 0.030(2) 0.0231(19) -0.0067(16) 0.0002(15) -0.0039(16)
C11 0.0236(18) 0.0239(19) 0.0194(17) -0.0073(15) 0.0016(14) -0.0050(14)
C12 0.0240(18) 0.0180(17) 0.0188(17) -0.0057(14) 0.0005(14) -0.0044(13)
C13 0.0254(18) 0.0209(18) 0.0174(17) -0.0083(14) 0.0018(14) 0.0001(14)
C14 0.045(2) 0.031(2) 0.0225(19) -0.0144(17) -0.0002(17) -0.0040(18)
C15 0.0180(17) 0.0204(17) 0.0143(15) -0.0070(13) 0.0008(12) -0.0003(13)
C16 0.0203(17) 0.0224(18) 0.0197(17) -0.0127(14) 0.0032(13) -0.0022(13)
C17 0.0207(18) 0.028(2) 0.0230(18) -0.0105(15) 0.0028(14) -0.0026(14)
C18 0.026(2) 0.032(2) 0.0263(19) -0.0129(17) -0.0034(15) 0.0027(16)
C19 0.0175(18) 0.035(2) 0.033(2) -0.0201(17) 0.0013(15) -0.0009(15)
C20 0.027(2) 0.033(2) 0.0273(19) -0.0164(17) 0.0096(15) -0.0099(16)
C21 0.0258(19) 0.0255(19) 0.0219(18) -0.0106(15) 0.0027(14) -0.0025(15)
C22 0.0213(17) 0.0202(17) 0.0133(15) -0.0063(13) -0.0009(13) -0.0019(13)
C23 0.0182(17) 0.0222(18) 0.0162(16) -0.0086(14) -0.0010(13) 0.0001(13)
C24 0.0178(17) 0.031(2) 0.0176(17) -0.0080(15) 0.0003(13) -0.0037(14)
C25 0.0232(18) 0.0235(19) 0.0203(17) -0.0029(15) -0.0025(14) -0.0057(14)
C26 0.030(2) 0.0174(17) 0.0224(18) -0.0057(14) -0.0029(15) 0.0008(14)
C27 0.0239(18) 0.0208(18) 0.0177(16) -0.0065(14) 0.0015(13) 0.0001(14)
C28 0.0163(17) 0.0233(18) 0.0253(18) -0.0134(15) 0.0047(13) -0.0032(13)
C29 0.034(2) 0.0223(19) 0.029(2) -0.0109(16) 0.0016(16) -0.0032(15)
C30 0.042(2) 0.019(2) 0.045(3) -0.0116(18) 0.001(2) -0.0030(17)
C31 0.034(2) 0.028(2) 0.049(3) -0.027(2) 0.0083(19) -0.0070(17)
C32 0.0240(19) 0.037(2) 0.033(2) -0.0238(18) 0.0068(15) -0.0075(16)
C33 0.0170(17) 0.0247(19) 0.0257(18) -0.0113(15) 0.0047(14) -0.0047(14)
C34 0.115(3) 0.110(3) 0.110(3) -0.0393(14) 0.0044(10) -0.0101(10)
C35 0.0423(13) 0.0323(12) 0.0303(12) -0.0120(9) -0.0005(9) -0.0014(9)
C36 0.0489(15) 0.0451(14) 0.0497(14) -0.0163(10) -0.0005(9) -0.0027(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
O1 S1 O2 122.15(18) .
O1 S1 N1 109.33(17) .
O2 S1 N1 108.83(17) .
O1 S1 N2 103.43(16) .
O2 S1 N2 104.96(16) .
N1 S1 N2 107.02(16) .
C2 N1 C1 115.7(3) .
C2 N1 S1 118.9(3) .
C1 N1 S1 117.0(3) .
C3 N2 C4 106.8(3) .
C3 N2 S1 127.9(3) .
C4 N2 S1 125.3(3) .
C3 N3 C5 106.5(3) .
C8 N4 C9 108.2(3) .
C8 N4 C14 126.0(3) .
C9 N4 C14 123.9(3) .
C12 N5 C13 117.3(3) .
C12 N5 C15 117.5(3) .
C13 N5 C15 117.3(3) .
N1 C1 H1A 109.5 .
N1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
N1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N1 C2 H2A 109.5 .
N1 C2 H2B 109.5 .
H2A C2 H2B 109.5 .
N1 C2 H2C 109.5 .
H2A C2 H2C 109.5 .
H2B C2 H2C 109.5 .
N3 C3 N2 111.6(3) .
N3 C3 H3 124.2 .
N2 C3 H3 124.2 .
C5 C4 N2 105.6(3) .
C5 C4 H4 127.2 .
N2 C4 H4 127.2 .
C4 C5 N3 109.5(3) .
C4 C5 C6 129.4(3) .
N3 C5 C6 121.1(3) .
C7 C6 C5 128.7(4) .
C7 C6 H6 115.6 .
C5 C6 H6 115.6 .
C6 C7 C8 129.5(3) .
C6 C7 C13 121.6(3) .
C8 C7 C13 108.5(3) .
N4 C8 C11 107.8(3) .
N4 C8 C7 132.0(3) .
C11 C8 C7 120.2(3) .
C10 C9 N4 109.4(3) .
C10 C9 H9 125.3 .
N4 C9 H9 125.3 .
C9 C10 C11 106.7(3) .
C9 C10 H10 126.6 .
C11 C10 H10 126.6 .
C8 C11 C10 107.8(3) .
C8 C11 C12 122.6(3) .
C10 C11 C12 129.6(3) .
O3 C12 N5 123.3(3) .
O3 C12 C11 121.7(3) .
N5 C12 C11 115.0(3) .
N5 C13 C7 110.6(3) .
N5 C13 H13A 109.5 .
C7 C13 H13A 109.5 .
N5 C13 H13B 109.5 .
C7 C13 H13B 109.5 .
H13A C13 H13B 108.1 .
N4 C14 H14A 109.5 .
N4 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
N4 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
N5 C15 C22 106.9(3) .
N5 C15 C16 109.5(3) .
C22 C15 C16 113.5(3) .
N5 C15 C28 111.0(3) .
C22 C15 C28 114.1(3) .
C16 C15 C28 101.8(3) .
C17 C16 C21 118.7(3) .
C17 C16 C15 122.5(3) .
C21 C16 C15 118.6(3) .
C16 C17 C18 120.3(3) .
C16 C17 H17 119.8 .
C18 C17 H17 119.8 .
C19 C18 C17 120.6(4) .
C19 C18 H18 119.7 .
C17 C18 H18 119.7 .
C18 C19 C20 119.3(3) .
C18 C19 H19 120.3 .
C20 C19 H19 120.3 .
C21 C20 C19 120.5(3) .
C21 C20 H20 119.8 .
C19 C20 H20 119.8 .
C20 C21 C16 120.6(3) .
C20 C21 H21 119.7 .
C16 C21 H21 119.7 .
C23 C22 C27 117.6(3) .
C23 C22 C15 123.2(3) .
C27 C22 C15 119.1(3) .
C22 C23 C24 121.0(3) .
C22 C23 H23 119.5 .
C24 C23 H23 119.5 .
C25 C24 C23 120.9(3) .
C25 C24 H24 119.6 .
C23 C24 H24 119.6 .
C24 C25 C26 118.8(3) .
C24 C25 H25 120.6 .
C26 C25 H25 120.6 .
C25 C26 C27 121.0(3) .
C25 C26 H26 119.5 .
C27 C26 H26 119.5 .
C26 C27 C22 120.7(3) .
C26 C27 H27 119.6 .
C22 C27 H27 119.6 .
C29 C28 C33 118.3(3) .
C29 C28 C15 122.6(3) .
C33 C28 C15 118.7(3) .
C28 C29 C30 120.4(4) .
C28 C29 H29 119.8 .
C30 C29 H29 119.8 .
C31 C30 C29 120.5(4) .
C31 C30 H30 119.7 .
C29 C30 H30 119.7 .
C30 C31 C32 120.0(4) .
C30 C31 H31 120.0 .
C32 C31 H31 120.0 .
C31 C32 C33 119.6(4) .
C31 C32 H32 120.2 .
C33 C32 H32 120.2 .
C32 C33 C28 121.2(4) .
C32 C33 H33 119.4 .
C28 C33 H33 119.4 .
C34 C35 C36 169.9(5) .
C34 C35 H35A 93.1 .
C36 C35 H35A 93.1 .
C34 C35 H35B 93.1 .
C36 C35 H35B 93.1 .
H35A C35 H35B 103.0 .
C36 C36 C35 136.6(6) 2_666
C36 C36 H36A 103.0 2_666
C35 C36 H36A 103.0 .
C36 C36 H36B 103.0 2_666
C35 C36 H36B 103.0 .
H36A C36 H36B 105.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.420(3) .
S1 O2 1.424(3) .
S1 N1 1.598(3) .
S1 N2 1.699(3) .
O3 C12 1.225(4) .
N1 C2 1.468(5) .
N1 C1 1.480(5) .
N2 C3 1.368(5) .
N2 C4 1.387(5) .
N3 C3 1.298(5) .
N3 C5 1.384(5) .
N4 C8 1.373(5) .
N4 C9 1.388(5) .
N4 C14 1.455(5) .
N5 C12 1.383(4) .
N5 C13 1.494(4) .
N5 C15 1.509(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3 0.9500 .
C4 C5 1.371(5) .
C4 H4 0.9500 .
C5 C6 1.459(5) .
C6 C7 1.345(5) .
C6 H6 0.9500 .
C7 C8 1.457(5) .
C7 C13 1.507(5) .
C8 C11 1.392(5) .
C9 C10 1.363(5) .
C9 H9 0.9500 .
C10 C11 1.420(5) .
C10 H10 0.9500 .
C11 C12 1.471(5) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C22 1.538(5) .
C15 C16 1.545(5) .
C15 C28 1.546(5) .
C16 C17 1.388(5) .
C16 C21 1.401(5) .
C17 C18 1.400(5) .
C17 H17 0.9500 .
C18 C19 1.375(6) .
C18 H18 0.9500 .
C19 C20 1.393(6) .
C19 H19 0.9500 .
C20 C21 1.381(5) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C23 1.392(5) .
C22 C27 1.406(5) .
C23 C24 1.392(5) .
C23 H23 0.9500 .
C24 C25 1.379(5) .
C24 H24 0.9500 .
C25 C26 1.383(5) .
C25 H25 0.9500 .
C26 C27 1.386(5) .
C26 H26 0.9500 .
C27 H27 0.9500 .
C28 C29 1.394(5) .
C28 C33 1.397(5) .
C29 C30 1.399(5) .
C29 H29 0.9500 .
C30 C31 1.375(6) .
C30 H30 0.9500 .
C31 C32 1.388(6) .
C31 H31 0.9500 .
C32 C33 1.394(5) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C34 C35 1.334(9) .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 C36 1.954(7) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C36 1.376(10) 2_666
C36 H36A 0.9900 .
C36 H36B 0.9900 .
|
1502011.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502011.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502011
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C26 H14 Br4'
_chemical_formula_weight 646.01
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 81.715(2)
_cell_angle_beta 76.668(3)
_cell_angle_gamma 79.787(3)
_cell_formula_units_Z 2
_cell_length_a 9.5315(6)
_cell_length_b 10.4853(5)
_cell_length_c 11.9199(6)
_cell_measurement_reflns_used 7362
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 67
_cell_measurement_theta_min 4
_cell_volume 1134.17(11)
_computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection 'APEX2-2009.3-0 (Bruker, 2009)'
_computing_data_reduction 'TWINABS-2008/2 (Bruker, 2008)'
_computing_molecular_graphics 'XP v5.1 (Bruker, 1998)'
_computing_publication_material 'XCIF-2008/2 (Bruker, 2008)'
_computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)'
_computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type 'Bruker APEX2 CCD detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0485
_diffrn_reflns_av_sigmaI/netI 0.0409
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 12663
_diffrn_reflns_theta_full 67.41
_diffrn_reflns_theta_max 67.41
_diffrn_reflns_theta_min 3.83
_exptl_absorpt_coefficient_mu 8.737
_exptl_absorpt_correction_T_max 0.6222
_exptl_absorpt_correction_T_min 0.1022
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
TWINABS. Program for empirical absorption correction of
area-detector data for twinned crystals.
University of Goetingen. Germany. Sheldrick, G. M. 2007
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.892
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 620
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.997
_refine_diff_density_min -0.698
_refine_diff_density_rms 0.149
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.127
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 272
_refine_ls_number_reflns 3774
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.127
_refine_ls_R_factor_all 0.0422
_refine_ls_R_factor_gt 0.0407
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+2.5630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1173
_refine_ls_wR_factor_ref 0.1195
_reflns_number_gt 3660
_reflns_number_total 3774
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_001.cif
_cod_data_source_block raj15t5
_cod_database_code 1502011
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.05201(7) 1.01280(5) 0.74046(5) 0.02855(19) Uani 1 1 d .
Br2 Br 0.35207(8) 0.72598(6) -0.07899(5) 0.03096(19) Uani 1 1 d .
Br3 Br 0.17204(7) 0.31735(6) 1.02766(5) 0.02753(19) Uani 1 1 d .
Br4 Br 0.41989(7) -0.02631(6) 0.19312(6) 0.03117(19) Uani 1 1 d .
C1 C 0.2543(6) 0.5539(5) 0.4461(5) 0.0179(11) Uani 1 1 d .
C2 C 0.2723(6) 0.4285(5) 0.4978(4) 0.0178(11) Uani 1 1 d .
C11 C 0.2112(6) 0.6630(5) 0.5165(5) 0.0188(11) Uani 1 1 d .
C12 C 0.1837(6) 0.6396(5) 0.6386(5) 0.0178(11) Uani 1 1 d .
C13 C 0.1368(6) 0.7473(5) 0.7038(5) 0.0194(11) Uani 1 1 d .
H13A H 0.1140 0.7335 0.7861 0.023 Uiso 1 1 calc R
C14 C 0.1239(6) 0.8713(5) 0.6490(5) 0.0206(11) Uani 1 1 d .
C15 C 0.1578(7) 0.8981(5) 0.5284(5) 0.0256(13) Uani 1 1 d .
H15A H 0.1512 0.9852 0.4923 0.031 Uiso 1 1 calc R
C16 C 0.2013(6) 0.7938(5) 0.4637(5) 0.0226(12) Uani 1 1 d .
H16A H 0.2252 0.8098 0.3816 0.027 Uiso 1 1 calc R
C21 C 0.2751(6) 0.5852(5) 0.3173(5) 0.0177(11) Uani 1 1 d .
C22 C 0.4144(6) 0.5693(6) 0.2482(5) 0.0231(12) Uani 1 1 d .
H22A H 0.4953 0.5317 0.2820 0.028 Uiso 1 1 calc R
C23 C 0.4364(7) 0.6089(6) 0.1277(5) 0.0247(12) Uani 1 1 d .
H23A H 0.5314 0.5967 0.0799 0.030 Uiso 1 1 calc R
C24 C 0.3197(7) 0.6647(5) 0.0813(4) 0.0200(11) Uani 1 1 d .
C25 C 0.1784(7) 0.6781(6) 0.1467(5) 0.0263(13) Uani 1 1 d .
H25A H 0.0978 0.7135 0.1117 0.032 Uiso 1 1 calc R
C26 C 0.1581(6) 0.6378(6) 0.2661(5) 0.0242(12) Uani 1 1 d .
H26A H 0.0623 0.6468 0.3128 0.029 Uiso 1 1 calc R
C31 C 0.2503(6) 0.4029(5) 0.6232(5) 0.0187(11) Uani 1 1 d .
C32 C 0.2034(6) 0.5076(5) 0.6937(4) 0.0169(10) Uani 1 1 d .
C33 C 0.1792(6) 0.4794(5) 0.8152(5) 0.0193(11) Uani 1 1 d .
H33A H 0.1484 0.5482 0.8633 0.023 Uiso 1 1 calc R
C34 C 0.2001(6) 0.3518(5) 0.8646(5) 0.0206(11) Uani 1 1 d .
C35 C 0.2436(6) 0.2476(5) 0.7970(5) 0.0208(11) Uani 1 1 d .
H35A H 0.2560 0.1604 0.8324 0.025 Uiso 1 1 calc R
C36 C 0.2684(6) 0.2737(5) 0.6778(5) 0.0200(11) Uani 1 1 d .
H36A H 0.2982 0.2033 0.6314 0.024 Uiso 1 1 calc R
C41 C 0.3104(6) 0.3171(5) 0.4259(4) 0.0162(10) Uani 1 1 d .
C42 C 0.2091(6) 0.2886(5) 0.3695(5) 0.0225(12) Uani 1 1 d .
H42A H 0.1156 0.3404 0.3782 0.027 Uiso 1 1 calc R
C43 C 0.2406(7) 0.1867(5) 0.3010(5) 0.0235(12) Uani 1 1 d .
H43A H 0.1705 0.1692 0.2623 0.028 Uiso 1 1 calc R
C44 C 0.3759(6) 0.1116(5) 0.2902(4) 0.0197(11) Uani 1 1 d .
C45 C 0.4811(6) 0.1347(5) 0.3445(5) 0.0246(12) Uani 1 1 d .
H45A H 0.5741 0.0819 0.3353 0.030 Uiso 1 1 calc R
C46 C 0.4465(7) 0.2382(6) 0.4134(5) 0.0245(12) Uani 1 1 d .
H46A H 0.5168 0.2550 0.4522 0.029 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0402(4) 0.0152(3) 0.0326(3) -0.0025(2) -0.0109(3) -0.0063(2)
Br2 0.0390(4) 0.0393(4) 0.0164(3) 0.0071(2) -0.0075(3) -0.0168(3)
Br3 0.0329(4) 0.0275(3) 0.0167(3) 0.0077(2) -0.0004(2) -0.0045(3)
Br4 0.0307(4) 0.0236(3) 0.0361(4) -0.0085(2) 0.0018(3) -0.0032(3)
C1 0.013(3) 0.021(2) 0.020(3) 0.001(2) -0.005(2) -0.004(2)
C2 0.014(3) 0.019(2) 0.020(3) 0.003(2) -0.003(2) -0.006(2)
C11 0.014(3) 0.017(2) 0.025(3) 0.002(2) -0.005(2) -0.003(2)
C12 0.011(3) 0.019(3) 0.025(3) 0.002(2) -0.007(2) -0.007(2)
C13 0.020(3) 0.018(2) 0.021(3) 0.002(2) -0.004(2) -0.008(2)
C14 0.022(3) 0.017(2) 0.024(3) -0.001(2) -0.004(2) -0.007(2)
C15 0.027(3) 0.018(3) 0.032(3) 0.008(2) -0.009(2) -0.010(2)
C16 0.026(3) 0.020(3) 0.020(3) 0.005(2) -0.004(2) -0.005(2)
C21 0.017(3) 0.014(2) 0.020(3) 0.0052(19) -0.005(2) -0.004(2)
C22 0.020(3) 0.029(3) 0.018(3) 0.003(2) -0.006(2) -0.001(2)
C23 0.022(3) 0.030(3) 0.018(3) 0.004(2) 0.000(2) -0.007(2)
C24 0.029(3) 0.021(3) 0.010(2) 0.0041(19) -0.005(2) -0.009(2)
C25 0.028(3) 0.028(3) 0.024(3) 0.002(2) -0.009(2) -0.006(2)
C26 0.020(3) 0.029(3) 0.020(3) 0.004(2) -0.002(2) -0.002(2)
C31 0.018(3) 0.017(2) 0.021(3) 0.004(2) -0.005(2) -0.007(2)
C32 0.012(3) 0.021(2) 0.017(2) 0.005(2) -0.003(2) -0.004(2)
C33 0.018(3) 0.018(2) 0.020(3) 0.002(2) -0.003(2) -0.004(2)
C34 0.020(3) 0.024(3) 0.017(3) 0.008(2) -0.005(2) -0.010(2)
C35 0.020(3) 0.017(2) 0.024(3) 0.008(2) -0.004(2) -0.006(2)
C36 0.019(3) 0.014(2) 0.024(3) 0.003(2) -0.003(2) -0.001(2)
C41 0.019(3) 0.015(2) 0.013(2) 0.0047(18) -0.001(2) -0.0040(19)
C42 0.018(3) 0.020(3) 0.024(3) 0.004(2) -0.001(2) 0.000(2)
C43 0.025(3) 0.022(3) 0.022(3) 0.006(2) -0.003(2) -0.009(2)
C44 0.023(3) 0.017(2) 0.016(2) -0.0007(19) 0.001(2) -0.005(2)
C45 0.020(3) 0.021(3) 0.026(3) 0.003(2) 0.004(2) -0.003(2)
C46 0.025(3) 0.027(3) 0.022(3) 0.003(2) -0.008(2) -0.007(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C11 120.4(5)
C2 C1 C21 122.2(5)
C11 C1 C21 117.4(4)
C1 C2 C31 120.2(5)
C1 C2 C41 120.2(5)
C31 C2 C41 119.6(4)
C12 C11 C16 119.0(5)
C12 C11 C1 120.1(5)
C16 C11 C1 120.9(5)
C13 C12 C11 118.5(5)
C13 C12 C32 121.7(5)
C11 C12 C32 119.8(5)
C14 C13 C12 120.3(5)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C13 C14 C15 122.6(5)
C13 C14 Br1 118.7(4)
C15 C14 Br1 118.7(4)
C16 C15 C14 117.7(5)
C16 C15 H15A 121.2
C14 C15 H15A 121.2
C15 C16 C11 121.8(5)
C15 C16 H16A 119.1
C11 C16 H16A 119.1
C26 C21 C22 119.1(5)
C26 C21 C1 120.9(5)
C22 C21 C1 119.9(5)
C21 C22 C23 120.3(5)
C21 C22 H22A 119.9
C23 C22 H22A 119.9
C24 C23 C22 119.0(5)
C24 C23 H23A 120.5
C22 C23 H23A 120.5
C23 C24 C25 122.4(5)
C23 C24 Br2 118.6(4)
C25 C24 Br2 119.0(4)
C24 C25 C26 117.9(5)
C24 C25 H25A 121.1
C26 C25 H25A 121.1
C21 C26 C25 121.3(5)
C21 C26 H26A 119.4
C25 C26 H26A 119.4
C36 C31 C32 118.7(5)
C36 C31 C2 120.8(5)
C32 C31 C2 120.4(5)
C33 C32 C31 119.0(5)
C33 C32 C12 121.9(5)
C31 C32 C12 119.1(5)
C34 C33 C32 120.1(5)
C34 C33 H33A 119.9
C32 C33 H33A 119.9
C33 C34 C35 121.7(5)
C33 C34 Br3 119.2(4)
C35 C34 Br3 119.1(4)
C36 C35 C34 118.8(5)
C36 C35 H35A 120.6
C34 C35 H35A 120.6
C35 C36 C31 121.5(5)
C35 C36 H36A 119.2
C31 C36 H36A 119.2
C42 C41 C46 118.0(5)
C42 C41 C2 120.1(5)
C46 C41 C2 121.9(5)
C43 C42 C41 121.9(5)
C43 C42 H42A 119.1
C41 C42 H42A 119.1
C44 C43 C42 118.4(5)
C44 C43 H43A 120.8
C42 C43 H43A 120.8
C43 C44 C45 122.4(5)
C43 C44 Br4 118.2(4)
C45 C44 Br4 119.4(4)
C44 C45 C46 118.1(5)
C44 C45 H45A 121.0
C46 C45 H45A 121.0
C41 C46 C45 121.2(5)
C41 C46 H46A 119.4
C45 C46 H46A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.903(5)
Br2 C24 1.899(5)
Br3 C34 1.890(5)
Br4 C44 1.910(5)
C1 C2 1.369(7)
C1 C11 1.461(7)
C1 C21 1.498(7)
C2 C31 1.452(7)
C2 C41 1.491(7)
C11 C12 1.411(8)
C11 C16 1.421(7)
C12 C13 1.411(7)
C12 C32 1.444(7)
C13 C14 1.367(7)
C13 H13A 0.9500
C14 C15 1.397(8)
C15 C16 1.377(8)
C15 H15A 0.9500
C16 H16A 0.9500
C21 C26 1.385(8)
C21 C22 1.387(8)
C22 C23 1.414(8)
C22 H22A 0.9500
C23 C24 1.358(8)
C23 H23A 0.9500
C24 C25 1.386(8)
C25 C26 1.405(8)
C25 H25A 0.9500
C26 H26A 0.9500
C31 C36 1.416(7)
C31 C32 1.424(7)
C32 C33 1.409(7)
C33 C34 1.381(7)
C33 H33A 0.9500
C34 C35 1.398(8)
C35 C36 1.380(8)
C35 H35A 0.9500
C36 H36A 0.9500
C41 C42 1.390(8)
C41 C46 1.398(8)
C42 C43 1.387(8)
C42 H42A 0.9500
C43 C44 1.375(8)
C43 H43A 0.9500
C44 C45 1.383(8)
C45 C46 1.402(8)
C45 H45A 0.9500
C46 H46A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C11 C1 C2 C31 -0.7(8)
C21 C1 C2 C31 -179.8(5)
C11 C1 C2 C41 177.6(5)
C21 C1 C2 C41 -1.5(8)
C2 C1 C11 C12 -1.9(8)
C21 C1 C11 C12 177.2(5)
C2 C1 C11 C16 176.0(5)
C21 C1 C11 C16 -4.9(8)
C16 C11 C12 C13 4.6(8)
C1 C11 C12 C13 -177.5(5)
C16 C11 C12 C32 -175.6(5)
C1 C11 C12 C32 2.3(8)
C11 C12 C13 C14 -2.4(8)
C32 C12 C13 C14 177.8(5)
C12 C13 C14 C15 -1.0(9)
C12 C13 C14 Br1 177.2(4)
C13 C14 C15 C16 2.1(9)
Br1 C14 C15 C16 -176.1(4)
C14 C15 C16 C11 0.2(9)
C12 C11 C16 C15 -3.6(8)
C1 C11 C16 C15 178.6(5)
C2 C1 C21 C26 111.9(6)
C11 C1 C21 C26 -67.2(7)
C2 C1 C21 C22 -72.2(7)
C11 C1 C21 C22 108.8(6)
C26 C21 C22 C23 1.3(8)
C1 C21 C22 C23 -174.7(5)
C21 C22 C23 C24 1.2(9)
C22 C23 C24 C25 -3.5(9)
C22 C23 C24 Br2 176.6(4)
C23 C24 C25 C26 3.1(8)
Br2 C24 C25 C26 -176.9(4)
C22 C21 C26 C25 -1.6(8)
C1 C21 C26 C25 174.3(5)
C24 C25 C26 C21 -0.5(8)
C1 C2 C31 C36 179.9(5)
C41 C2 C31 C36 1.7(8)
C1 C2 C31 C32 2.9(8)
C41 C2 C31 C32 -175.4(5)
C36 C31 C32 C33 1.1(8)
C2 C31 C32 C33 178.3(5)
C36 C31 C32 C12 -179.5(5)
C2 C31 C32 C12 -2.4(8)
C13 C12 C32 C33 -1.0(8)
C11 C12 C32 C33 179.2(5)
C13 C12 C32 C31 179.7(5)
C11 C12 C32 C31 -0.2(7)
C31 C32 C33 C34 -0.3(8)
C12 C32 C33 C34 -179.6(5)
C32 C33 C34 C35 -0.8(9)
C32 C33 C34 Br3 178.2(4)
C33 C34 C35 C36 1.0(9)
Br3 C34 C35 C36 -178.0(4)
C34 C35 C36 C31 -0.1(8)
C32 C31 C36 C35 -0.9(8)
C2 C31 C36 C35 -178.0(5)
C1 C2 C41 C42 -68.9(7)
C31 C2 C41 C42 109.4(6)
C1 C2 C41 C46 111.5(6)
C31 C2 C41 C46 -70.2(7)
C46 C41 C42 C43 -1.0(8)
C2 C41 C42 C43 179.4(5)
C41 C42 C43 C44 0.7(8)
C42 C43 C44 C45 -0.4(8)
C42 C43 C44 Br4 -178.7(4)
C43 C44 C45 C46 0.5(8)
Br4 C44 C45 C46 178.8(4)
C42 C41 C46 C45 1.1(8)
C2 C41 C46 C45 -179.3(5)
C44 C45 C46 C41 -0.8(8)
|
1502012.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502012.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502012
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C30 H26'
_chemical_formula_weight 386.51
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 104.931(6)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 10.9572(11)
_cell_length_b 10.3404(12)
_cell_length_c 19.780(2)
_cell_measurement_reflns_used 2368
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 60
_cell_measurement_theta_min 4
_cell_volume 2165.4(4)
_computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)'
_computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)'
_computing_molecular_graphics 'XP v5.1 (Bruker, 1998)'
_computing_publication_material 'XCIF-2008/2 (Bruker, 2008)'
_computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)'
_computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type 'Bruker APEX2 CCD detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0724
_diffrn_reflns_av_sigmaI/netI 0.0614
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 17345
_diffrn_reflns_theta_full 67.64
_diffrn_reflns_theta_max 67.64
_diffrn_reflns_theta_min 4.22
_exptl_absorpt_coefficient_mu 0.501
_exptl_absorpt_correction_T_max 0.9802
_exptl_absorpt_correction_T_min 0.8323
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS. Program for empirical absorption correction of
area-detector data. University of Goetingen. Germany.
Sheldrick, G. M. 1996
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.186
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 824
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.04
_refine_diff_density_max 0.246
_refine_diff_density_min -0.177
_refine_diff_density_rms 0.045
_refine_ls_extinction_coef 0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.998
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 276
_refine_ls_number_reflns 3718
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.998
_refine_ls_R_factor_all 0.0938
_refine_ls_R_factor_gt 0.0550
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.6652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1302
_refine_ls_wR_factor_ref 0.1506
_reflns_number_gt 2430
_reflns_number_total 3718
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_002.cif
_cod_data_source_block raj15y
_cod_original_sg_symbol_H-M 'P 21/n'
_cod_database_code 1502012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5952(2) 0.3738(2) 0.61274(12) 0.0347(6) Uani 1 1 d .
C2 C 0.5660(2) 0.4894(2) 0.63735(12) 0.0340(6) Uani 1 1 d .
C11 C 0.5122(2) 0.2630(2) 0.60818(12) 0.0332(6) Uani 1 1 d .
C12 C 0.3963(2) 0.2769(2) 0.62757(12) 0.0333(6) Uani 1 1 d .
C13 C 0.3160(2) 0.1684(3) 0.62049(13) 0.0377(6) Uani 1 1 d .
H13A H 0.2380 0.1774 0.6327 0.045 Uiso 1 1 calc R
C14 C 0.3450(2) 0.0501(3) 0.59683(13) 0.0381(6) Uani 1 1 d .
C15 C 0.4617(2) 0.0381(3) 0.58023(13) 0.0397(6) Uani 1 1 d .
H15A H 0.4852 -0.0432 0.5651 0.048 Uiso 1 1 calc R
C16 C 0.5418(2) 0.1407(2) 0.58533(13) 0.0374(6) Uani 1 1 d .
H16A H 0.6195 0.1294 0.5732 0.045 Uiso 1 1 calc R
C17 C 0.2542(3) -0.0616(3) 0.58825(16) 0.0521(8) Uani 1 1 d .
H17A H 0.2013 -0.0518 0.6210 0.078 Uiso 1 1 calc R
H17B H 0.3017 -0.1427 0.5979 0.078 Uiso 1 1 calc R
H17C H 0.2006 -0.0628 0.5402 0.078 Uiso 1 1 calc R
C21 C 0.7117(2) 0.3577(2) 0.58684(13) 0.0338(6) Uani 1 1 d .
C22 C 0.7141(2) 0.4042(2) 0.52123(13) 0.0371(6) Uani 1 1 d .
H22A H 0.6438 0.4515 0.4944 0.045 Uiso 1 1 calc R
C23 C 0.8171(2) 0.3828(3) 0.49418(13) 0.0382(6) Uani 1 1 d .
H23A H 0.8160 0.4155 0.4492 0.046 Uiso 1 1 calc R
C24 C 0.9214(2) 0.3146(2) 0.53143(13) 0.0370(6) Uani 1 1 d .
C25 C 0.9202(2) 0.2698(2) 0.59758(14) 0.0380(6) Uani 1 1 d .
H25A H 0.9912 0.2237 0.6246 0.046 Uiso 1 1 calc R
C26 C 0.8169(2) 0.2914(2) 0.62497(13) 0.0376(6) Uani 1 1 d .
H26A H 0.8186 0.2602 0.6704 0.045 Uiso 1 1 calc R
C27 C 1.0307(2) 0.2877(3) 0.49994(14) 0.0457(7) Uani 1 1 d .
H27A H 1.0059 0.3083 0.4499 0.069 Uiso 1 1 calc R
H27B H 1.0539 0.1961 0.5062 0.069 Uiso 1 1 calc R
H27C H 1.1031 0.3411 0.5233 0.069 Uiso 1 1 calc R
C31 C 0.4504(2) 0.5050(2) 0.65920(12) 0.0347(6) Uani 1 1 d .
C32 C 0.3646(2) 0.4008(2) 0.65327(12) 0.0349(6) Uani 1 1 d .
C33 C 0.2504(2) 0.4212(3) 0.67175(13) 0.0371(6) Uani 1 1 d .
H33A H 0.1926 0.3513 0.6677 0.044 Uiso 1 1 calc R
C34 C 0.2191(2) 0.5386(3) 0.69553(13) 0.0404(6) Uani 1 1 d .
C35 C 0.3065(2) 0.6398(3) 0.70320(13) 0.0415(6) Uani 1 1 d .
H35A H 0.2880 0.7207 0.7211 0.050 Uiso 1 1 calc R
C36 C 0.4186(2) 0.6239(3) 0.68527(13) 0.0399(6) Uani 1 1 d .
H36A H 0.4759 0.6944 0.6905 0.048 Uiso 1 1 calc R
C37 C 0.0907(2) 0.5587(3) 0.70909(15) 0.0495(7) Uani 1 1 d .
H37A H 0.0850 0.6468 0.7262 0.074 Uiso 1 1 calc R
H37B H 0.0791 0.4965 0.7443 0.074 Uiso 1 1 calc R
H37C H 0.0248 0.5456 0.6656 0.074 Uiso 1 1 calc R
C41 C 0.6516(2) 0.6043(2) 0.64159(13) 0.0348(6) Uani 1 1 d .
C42 C 0.7462(2) 0.6301(2) 0.70178(13) 0.0378(6) Uani 1 1 d .
H42A H 0.7571 0.5746 0.7412 0.045 Uiso 1 1 calc R
C43 C 0.8250(2) 0.7364(3) 0.70490(13) 0.0386(6) Uani 1 1 d .
H43A H 0.8879 0.7537 0.7469 0.046 Uiso 1 1 calc R
C44 C 0.8139(2) 0.8178(3) 0.64792(14) 0.0387(6) Uani 1 1 d .
C45 C 0.7188(2) 0.7919(3) 0.58812(14) 0.0400(6) Uani 1 1 d .
H45A H 0.7088 0.8467 0.5485 0.048 Uiso 1 1 calc R
C46 C 0.6379(2) 0.6874(3) 0.58479(13) 0.0399(6) Uani 1 1 d .
H46A H 0.5726 0.6725 0.5434 0.048 Uiso 1 1 calc R
C47 C 0.9030(3) 0.9305(3) 0.65151(15) 0.0485(7) Uani 1 1 d .
H47A H 0.9902 0.9011 0.6705 0.073 Uiso 1 1 calc R
H47B H 0.8833 0.9977 0.6820 0.073 Uiso 1 1 calc R
H47C H 0.8935 0.9658 0.6045 0.073 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0333(13) 0.0421(16) 0.0296(13) 0.0015(11) 0.0097(10) -0.0005(11)
C2 0.0324(13) 0.0397(16) 0.0299(13) 0.0031(10) 0.0080(10) 0.0001(10)
C11 0.0312(13) 0.0396(15) 0.0285(13) 0.0010(10) 0.0073(10) -0.0007(10)
C12 0.0319(12) 0.0413(16) 0.0279(12) 0.0013(10) 0.0101(10) 0.0002(10)
C13 0.0322(13) 0.0451(17) 0.0378(14) 0.0032(11) 0.0127(11) -0.0025(11)
C14 0.0385(14) 0.0401(16) 0.0375(15) 0.0020(11) 0.0128(11) -0.0027(11)
C15 0.0405(14) 0.0392(16) 0.0401(16) -0.0045(11) 0.0116(12) -0.0018(11)
C16 0.0348(14) 0.0439(17) 0.0351(14) -0.0015(11) 0.0117(11) 0.0017(11)
C17 0.0475(16) 0.0468(18) 0.066(2) -0.0026(14) 0.0219(15) -0.0090(13)
C21 0.0299(12) 0.0379(15) 0.0361(14) -0.0045(11) 0.0131(11) -0.0035(10)
C22 0.0363(14) 0.0391(16) 0.0374(15) -0.0003(11) 0.0122(11) -0.0006(11)
C23 0.0394(14) 0.0455(16) 0.0330(14) -0.0023(11) 0.0154(11) -0.0048(11)
C24 0.0332(13) 0.0415(16) 0.0391(15) -0.0046(11) 0.0146(11) -0.0054(11)
C25 0.0286(12) 0.0427(16) 0.0443(15) 0.0009(12) 0.0124(11) -0.0008(11)
C26 0.0349(13) 0.0431(16) 0.0373(14) 0.0028(11) 0.0136(11) -0.0018(11)
C27 0.0365(14) 0.0560(19) 0.0489(17) -0.0033(13) 0.0188(12) -0.0036(12)
C31 0.0347(13) 0.0411(16) 0.0291(13) 0.0000(10) 0.0097(10) 0.0000(11)
C32 0.0341(13) 0.0401(16) 0.0317(14) 0.0020(11) 0.0110(11) -0.0005(11)
C33 0.0349(13) 0.0448(16) 0.0333(14) -0.0002(11) 0.0120(11) -0.0042(11)
C34 0.0378(14) 0.0544(18) 0.0318(14) -0.0003(12) 0.0140(11) 0.0021(12)
C35 0.0432(15) 0.0471(17) 0.0370(15) -0.0052(12) 0.0156(12) 0.0034(12)
C36 0.0387(14) 0.0461(17) 0.0370(15) -0.0031(11) 0.0136(12) -0.0017(12)
C37 0.0406(15) 0.068(2) 0.0453(17) -0.0051(14) 0.0203(13) 0.0036(13)
C41 0.0304(13) 0.0392(15) 0.0371(14) -0.0009(11) 0.0130(11) 0.0028(10)
C42 0.0366(14) 0.0451(16) 0.0344(14) -0.0003(11) 0.0138(11) 0.0020(11)
C43 0.0319(13) 0.0513(17) 0.0346(14) -0.0097(11) 0.0123(11) -0.0020(11)
C44 0.0361(14) 0.0415(16) 0.0444(16) -0.0045(12) 0.0208(12) -0.0013(11)
C45 0.0396(14) 0.0398(16) 0.0439(16) 0.0031(12) 0.0166(12) -0.0001(11)
C46 0.0356(14) 0.0460(17) 0.0365(15) 0.0002(12) 0.0066(11) -0.0020(11)
C47 0.0481(16) 0.0520(18) 0.0501(18) -0.0073(13) 0.0213(13) -0.0077(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C11 121.0(2)
C2 C1 C21 121.2(2)
C11 C1 C21 117.7(2)
C1 C2 C31 120.6(2)
C1 C2 C41 121.0(2)
C31 C2 C41 118.4(2)
C16 C11 C12 118.1(2)
C16 C11 C1 122.4(2)
C12 C11 C1 119.5(2)
C13 C12 C11 118.0(2)
C13 C12 C32 122.5(2)
C11 C12 C32 119.5(2)
C14 C13 C12 123.2(2)
C14 C13 H13A 118.4
C12 C13 H13A 118.4
C13 C14 C15 117.5(2)
C13 C14 C17 121.1(2)
C15 C14 C17 121.4(2)
C16 C15 C14 121.4(2)
C16 C15 H15A 119.3
C14 C15 H15A 119.3
C15 C16 C11 121.7(2)
C15 C16 H16A 119.2
C11 C16 H16A 119.2
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C26 C21 C22 117.7(2)
C26 C21 C1 122.0(2)
C22 C21 C1 120.2(2)
C23 C22 C21 121.2(2)
C23 C22 H22A 119.4
C21 C22 H22A 119.4
C24 C23 C22 121.3(2)
C24 C23 H23A 119.3
C22 C23 H23A 119.3
C23 C24 C25 117.6(2)
C23 C24 C27 120.6(2)
C25 C24 C27 121.8(2)
C24 C25 C26 121.2(2)
C24 C25 H25A 119.4
C26 C25 H25A 119.4
C21 C26 C25 120.9(2)
C21 C26 H26A 119.6
C25 C26 H26A 119.6
C24 C27 H27A 109.5
C24 C27 H27B 109.5
H27A C27 H27B 109.5
C24 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C36 C31 C32 118.2(2)
C36 C31 C2 121.5(2)
C32 C31 C2 120.2(2)
C33 C32 C31 118.7(2)
C33 C32 C12 122.1(2)
C31 C32 C12 119.2(2)
C34 C33 C32 122.5(2)
C34 C33 H33A 118.7
C32 C33 H33A 118.7
C33 C34 C35 118.2(2)
C33 C34 C37 120.4(2)
C35 C34 C37 121.4(2)
C36 C35 C34 121.0(2)
C36 C35 H35A 119.5
C34 C35 H35A 119.5
C35 C36 C31 121.3(2)
C35 C36 H36A 119.3
C31 C36 H36A 119.3
C34 C37 H37A 109.5
C34 C37 H37B 109.5
H37A C37 H37B 109.5
C34 C37 H37C 109.5
H37A C37 H37C 109.5
H37B C37 H37C 109.5
C42 C41 C46 118.4(2)
C42 C41 C2 121.1(2)
C46 C41 C2 120.5(2)
C41 C42 C43 120.5(2)
C41 C42 H42A 119.7
C43 C42 H42A 119.7
C44 C43 C42 121.4(2)
C44 C43 H43A 119.3
C42 C43 H43A 119.3
C45 C44 C43 117.7(2)
C45 C44 C47 121.6(2)
C43 C44 C47 120.6(2)
C44 C45 C46 121.4(2)
C44 C45 H45A 119.3
C46 C45 H45A 119.3
C45 C46 C41 120.5(2)
C45 C46 H46A 119.8
C41 C46 H46A 119.8
C44 C47 H47A 109.5
C44 C47 H47B 109.5
H47A C47 H47B 109.5
C44 C47 H47C 109.5
H47A C47 H47C 109.5
H47B C47 H47C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.359(3)
C1 C11 1.451(3)
C1 C21 1.502(3)
C2 C31 1.450(3)
C2 C41 1.503(3)
C11 C16 1.409(3)
C11 C12 1.426(3)
C12 C13 1.410(3)
C12 C32 1.453(3)
C13 C14 1.375(4)
C13 H13A 0.9500
C14 C15 1.405(3)
C14 C17 1.505(4)
C15 C16 1.365(3)
C15 H15A 0.9500
C16 H16A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C21 C26 1.386(3)
C21 C22 1.391(3)
C22 C23 1.385(3)
C22 H22A 0.9500
C23 C24 1.383(3)
C23 H23A 0.9500
C24 C25 1.391(4)
C24 C27 1.511(3)
C25 C26 1.393(3)
C25 H25A 0.9500
C26 H26A 0.9500
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C31 C36 1.411(3)
C31 C32 1.415(3)
C32 C33 1.408(3)
C33 C34 1.377(4)
C33 H33A 0.9500
C34 C35 1.400(4)
C34 C37 1.513(3)
C35 C36 1.373(3)
C35 H35A 0.9500
C36 H36A 0.9500
C37 H37A 0.9800
C37 H37B 0.9800
C37 H37C 0.9800
C41 C42 1.388(3)
C41 C46 1.391(3)
C42 C43 1.389(3)
C42 H42A 0.9500
C43 C44 1.387(4)
C43 H43A 0.9500
C44 C45 1.386(4)
C44 C47 1.510(4)
C45 C46 1.388(3)
C45 H45A 0.9500
C46 H46A 0.9500
C47 H47A 0.9800
C47 H47B 0.9800
C47 H47C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C11 C1 C2 C31 -0.5(4)
C21 C1 C2 C31 177.2(2)
C11 C1 C2 C41 -179.6(2)
C21 C1 C2 C41 -1.9(3)
C2 C1 C11 C16 -177.6(2)
C21 C1 C11 C16 4.6(3)
C2 C1 C11 C12 2.2(3)
C21 C1 C11 C12 -175.6(2)
C16 C11 C12 C13 -2.1(3)
C1 C11 C12 C13 178.1(2)
C16 C11 C12 C32 178.3(2)
C1 C11 C12 C32 -1.6(3)
C11 C12 C13 C14 0.9(4)
C32 C12 C13 C14 -179.4(2)
C12 C13 C14 C15 1.1(4)
C12 C13 C14 C17 -178.2(2)
C13 C14 C15 C16 -1.9(4)
C17 C14 C15 C16 177.3(2)
C14 C15 C16 C11 0.7(4)
C12 C11 C16 C15 1.3(4)
C1 C11 C16 C15 -178.9(2)
C2 C1 C21 C26 106.4(3)
C11 C1 C21 C26 -75.9(3)
C2 C1 C21 C22 -76.9(3)
C11 C1 C21 C22 100.8(3)
C26 C21 C22 C23 1.3(4)
C1 C21 C22 C23 -175.5(2)
C21 C22 C23 C24 -0.1(4)
C22 C23 C24 C25 -0.9(4)
C22 C23 C24 C27 177.6(2)
C23 C24 C25 C26 0.8(4)
C27 C24 C25 C26 -177.7(2)
C22 C21 C26 C25 -1.4(4)
C1 C21 C26 C25 175.4(2)
C24 C25 C26 C21 0.3(4)
C1 C2 C31 C36 179.6(2)
C41 C2 C31 C36 -1.3(3)
C1 C2 C31 C32 -1.8(3)
C41 C2 C31 C32 177.3(2)
C36 C31 C32 C33 1.7(3)
C2 C31 C32 C33 -176.9(2)
C36 C31 C32 C12 -179.0(2)
C2 C31 C32 C12 2.3(3)
C13 C12 C32 C33 -1.1(4)
C11 C12 C32 C33 178.6(2)
C13 C12 C32 C31 179.7(2)
C11 C12 C32 C31 -0.6(3)
C31 C32 C33 C34 -0.2(4)
C12 C32 C33 C34 -179.4(2)
C32 C33 C34 C35 -1.8(4)
C32 C33 C34 C37 175.0(2)
C33 C34 C35 C36 2.2(4)
C37 C34 C35 C36 -174.6(2)
C34 C35 C36 C31 -0.6(4)
C32 C31 C36 C35 -1.3(4)
C2 C31 C36 C35 177.3(2)
C1 C2 C41 C42 -91.4(3)
C31 C2 C41 C42 89.5(3)
C1 C2 C41 C46 88.4(3)
C31 C2 C41 C46 -90.7(3)
C46 C41 C42 C43 0.0(4)
C2 C41 C42 C43 179.7(2)
C41 C42 C43 C44 -1.5(4)
C42 C43 C44 C45 1.8(4)
C42 C43 C44 C47 -178.1(2)
C43 C44 C45 C46 -0.6(4)
C47 C44 C45 C46 179.3(2)
C44 C45 C46 C41 -1.0(4)
C42 C41 C46 C45 1.3(4)
C2 C41 C46 C45 -178.5(2)
|
1502013.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502013
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C28.33 H22.33 Cl'
_chemical_formula_weight 398.25
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 108.7570(10)
_cell_angle_beta 100.3990(10)
_cell_angle_gamma 100.0760(10)
_cell_formula_units_Z 6
_cell_length_a 9.8526(2)
_cell_length_b 18.1426(3)
_cell_length_c 19.4664(3)
_cell_measurement_reflns_used 9732
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 67
_cell_measurement_theta_min 3
_cell_volume 3137.68(10)
_computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)'
_computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)'
_computing_molecular_graphics 'XP v5.1 (Bruker, 1998)'
_computing_publication_material 'XCIF-2008/2 (Bruker, 2008)'
_computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)'
_computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type 'Bruker APEX2 CCD detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0214
_diffrn_reflns_av_sigmaI/netI 0.0252
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 25938
_diffrn_reflns_theta_full 67.81
_diffrn_reflns_theta_max 67.81
_diffrn_reflns_theta_min 2.66
_exptl_absorpt_coefficient_mu 1.683
_exptl_absorpt_correction_T_max 0.8913
_exptl_absorpt_correction_T_min 0.5383
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS. Program for empirical absorption correction of
area-detector data. University of Goetingen. Germany.
Sheldrick, G. M. 1996
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.265
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1256
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.07
_refine_diff_density_max 0.257
_refine_diff_density_min -0.345
_refine_diff_density_rms 0.041
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 799
_refine_ls_number_reflns 10672
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.020
_refine_ls_R_factor_all 0.0462
_refine_ls_R_factor_gt 0.0371
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+1.0711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0960
_refine_ls_wR_factor_ref 0.1005
_reflns_number_gt 8939
_reflns_number_total 10672
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_003.cif
_cod_data_source_block raj16c
_cod_database_code 1502013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.42645(17) 0.27288(9) 0.40291(8) 0.0169(3) Uani 1 1 d .
C2 C 0.28958(17) 0.24204(9) 0.40281(8) 0.0166(3) Uani 1 1 d .
C11 C 0.47035(17) 0.35384(9) 0.40375(8) 0.0176(3) Uani 1 1 d .
C12 C 0.36928(17) 0.40012(9) 0.39971(8) 0.0183(3) Uani 1 1 d .
C13 C 0.41620(18) 0.47856(10) 0.40058(9) 0.0198(3) Uani 1 1 d .
H13A H 0.3484 0.5093 0.3969 0.024 Uiso 1 1 calc R
C14 C 0.55615(18) 0.51222(9) 0.40660(9) 0.0196(3) Uani 1 1 d .
C15 C 0.65599(18) 0.46631(10) 0.41297(9) 0.0220(4) Uani 1 1 d .
H15A H 0.7538 0.4891 0.4188 0.026 Uiso 1 1 calc R
C16 C 0.61421(18) 0.38937(10) 0.41088(9) 0.0213(3) Uani 1 1 d .
H16A H 0.6833 0.3593 0.4143 0.026 Uiso 1 1 calc R
C17 C 0.60380(19) 0.59606(10) 0.40741(10) 0.0238(4) Uani 1 1 d .
H17A H 0.5245 0.6220 0.4097 0.036 Uiso 1 1 calc R
H17B H 0.6343 0.5935 0.3617 0.036 Uiso 1 1 calc R
H17C H 0.6836 0.6273 0.4513 0.036 Uiso 1 1 calc R
C21 C 0.53176(17) 0.22217(9) 0.40118(9) 0.0176(3) Uani 1 1 d .
C22 C 0.62042(18) 0.22378(10) 0.46613(9) 0.0209(3) Uani 1 1 d .
H22A H 0.6200 0.2609 0.5134 0.025 Uiso 1 1 calc R
C23 C 0.70983(18) 0.17192(10) 0.46309(9) 0.0225(4) Uani 1 1 d .
H23A H 0.7691 0.1741 0.5083 0.027 Uiso 1 1 calc R
C24 C 0.71386(18) 0.11708(10) 0.39505(10) 0.0205(3) Uani 1 1 d .
C25 C 0.62853(18) 0.11718(10) 0.32957(9) 0.0214(4) Uani 1 1 d .
H25A H 0.6316 0.0814 0.2823 0.026 Uiso 1 1 calc R
C26 C 0.53930(17) 0.16882(9) 0.33258(9) 0.0191(3) Uani 1 1 d .
H26A H 0.4824 0.1679 0.2872 0.023 Uiso 1 1 calc R
C27 C 0.80721(19) 0.05888(11) 0.39216(11) 0.0277(4) Uani 1 1 d .
H27A H 0.7487 0.0038 0.3649 0.042 Uiso 1 1 calc R
H27B H 0.8531 0.0647 0.4433 0.042 Uiso 1 1 calc R
H27C H 0.8804 0.0704 0.3664 0.042 Uiso 1 1 calc R
C31 C 0.18376(17) 0.28792(9) 0.39854(8) 0.0174(3) Uani 1 1 d .
C32 C 0.22224(18) 0.36562(10) 0.39597(8) 0.0188(3) Uani 1 1 d .
C33 C 0.11438(19) 0.40702(10) 0.38903(10) 0.0249(4) Uani 1 1 d .
H33A H 0.1384 0.4594 0.3875 0.030 Uiso 1 1 calc R
C34 C -0.02421(19) 0.37290(11) 0.38451(11) 0.0279(4) Uani 1 1 d .
H34A H -0.0948 0.4017 0.3797 0.033 Uiso 1 1 calc R
C35 C -0.06243(19) 0.29599(11) 0.38699(10) 0.0254(4) Uani 1 1 d .
H35A H -0.1587 0.2725 0.3835 0.030 Uiso 1 1 calc R
C36 C 0.03998(18) 0.25476(10) 0.39447(9) 0.0205(3) Uani 1 1 d .
H36A H 0.0140 0.2029 0.3970 0.025 Uiso 1 1 calc R
C41 C 0.24660(16) 0.16151(9) 0.40904(9) 0.0174(3) Uani 1 1 d .
C42 C 0.22020(17) 0.09013(10) 0.34765(9) 0.0209(3) Uani 1 1 d .
H42A H 0.2284 0.0921 0.3004 0.025 Uiso 1 1 calc R
C43 C 0.18213(18) 0.01647(10) 0.35505(10) 0.0227(4) Uani 1 1 d .
H43A H 0.1658 -0.0317 0.3130 0.027 Uiso 1 1 calc R
C44 C 0.16776(18) 0.01239(10) 0.42310(10) 0.0241(4) Uani 1 1 d .
H44A H 0.1415 -0.0383 0.4279 0.029 Uiso 1 1 calc R
C45 C 0.19189(19) 0.08282(10) 0.48443(10) 0.0252(4) Uani 1 1 d .
H45A H 0.1815 0.0805 0.5313 0.030 Uiso 1 1 calc R
C46 C 0.23123(18) 0.15663(10) 0.47724(9) 0.0218(4) Uani 1 1 d .
H46A H 0.2480 0.2046 0.5195 0.026 Uiso 1 1 calc R
C1A C 0.10656(16) 0.24579(9) 0.91502(9) 0.0169(3) Uani 1 1 d .
C2A C 0.10099(16) 0.18021(9) 0.85416(9) 0.0176(3) Uani 1 1 d .
C11A C 0.12057(16) 0.24057(9) 0.98853(9) 0.0175(3) Uani 1 1 d .
C12A C 0.12444(16) 0.16654(9) 0.99785(9) 0.0179(3) Uani 1 1 d .
C13A C 0.13471(17) 0.16362(10) 1.07011(9) 0.0200(3) Uani 1 1 d .
H13B H 0.1343 0.1137 1.0763 0.024 Uiso 1 1 calc R
C14A C 0.14529(18) 0.23021(10) 1.13211(9) 0.0214(3) Uani 1 1 d .
C15A C 0.14442(18) 0.30346(10) 1.12216(9) 0.0216(4) Uani 1 1 d .
H15B H 0.1522 0.3502 1.1642 0.026 Uiso 1 1 calc R
C16A C 0.13256(17) 0.30862(10) 1.05262(9) 0.0202(3) Uani 1 1 d .
H16B H 0.1324 0.3589 1.0474 0.024 Uiso 1 1 calc R
C17A C 0.1598(2) 0.22646(11) 1.20914(10) 0.0282(4) Uani 1 1 d .
H17D H 0.1548 0.1710 1.2059 0.042 Uiso 1 1 calc R
H17E H 0.0825 0.2446 1.2295 0.042 Uiso 1 1 calc R
H17F H 0.2517 0.2613 1.2421 0.042 Uiso 1 1 calc R
C21A C 0.10203(17) 0.32489(9) 0.90719(8) 0.0180(3) Uani 1 1 d .
C22A C -0.01755(18) 0.35529(10) 0.91223(9) 0.0207(3) Uani 1 1 d .
H22B H -0.0990 0.3247 0.9191 0.025 Uiso 1 1 calc R
C23A C -0.01935(19) 0.42958(10) 0.90730(9) 0.0226(4) Uani 1 1 d .
H23B H -0.1023 0.4490 0.9106 0.027 Uiso 1 1 calc R
C24A C 0.09920(18) 0.47645(10) 0.89756(9) 0.0202(3) Uani 1 1 d .
C25A C 0.21689(18) 0.44479(10) 0.89096(9) 0.0211(3) Uani 1 1 d .
H25B H 0.2978 0.4749 0.8831 0.025 Uiso 1 1 calc R
C26A C 0.21888(18) 0.37029(10) 0.89557(9) 0.0199(3) Uani 1 1 d .
H26B H 0.3007 0.3501 0.8908 0.024 Uiso 1 1 calc R
C27A C 0.1001(2) 0.55903(10) 0.89717(10) 0.0265(4) Uani 1 1 d .
H27D H 0.0173 0.5561 0.8590 0.040 Uiso 1 1 calc R
H27E H 0.1877 0.5810 0.8856 0.040 Uiso 1 1 calc R
H27F H 0.0960 0.5940 0.9466 0.040 Uiso 1 1 calc R
C31A C 0.10884(16) 0.10416(9) 0.86196(9) 0.0177(3) Uani 1 1 d .
C32A C 0.10217(17) 0.03570(10) 0.79916(9) 0.0208(3) Uani 1 1 d .
H32A H 0.0925 0.0398 0.7511 0.025 Uiso 1 1 calc R
C33A C 0.10948(18) -0.03651(10) 0.80647(9) 0.0227(4) Uani 1 1 d .
H33B H 0.1045 -0.0818 0.7637 0.027 Uiso 1 1 calc R
C34A C 0.12421(18) -0.04315(10) 0.87689(10) 0.0227(4) Uani 1 1 d .
H34B H 0.1311 -0.0927 0.8821 0.027 Uiso 1 1 calc R
C35A C 0.12867(17) 0.02200(10) 0.93849(9) 0.0208(3) Uani 1 1 d .
H35B H 0.1377 0.0165 0.9859 0.025 Uiso 1 1 calc R
C36A C 0.12012(16) 0.09698(9) 0.93307(9) 0.0177(3) Uani 1 1 d .
C41A C 0.08451(17) 0.18749(9) 0.77879(9) 0.0175(3) Uani 1 1 d .
C42A C -0.04173(17) 0.19899(9) 0.74316(9) 0.0189(3) Uani 1 1 d .
H42B H -0.1189 0.2006 0.7662 0.023 Uiso 1 1 calc R
C43A C -0.05575(18) 0.20810(10) 0.67417(9) 0.0217(4) Uani 1 1 d .
H43B H -0.1425 0.2155 0.6502 0.026 Uiso 1 1 calc R
C44A C 0.05669(19) 0.20640(10) 0.64018(9) 0.0239(4) Uani 1 1 d .
H44B H 0.0472 0.2128 0.5931 0.029 Uiso 1 1 calc R
C45A C 0.18259(19) 0.19540(10) 0.67536(9) 0.0246(4) Uani 1 1 d .
H45B H 0.2600 0.1946 0.6525 0.030 Uiso 1 1 calc R
C46A C 0.19657(18) 0.18548(10) 0.74387(9) 0.0217(4) Uani 1 1 d .
H46B H 0.2830 0.1773 0.7672 0.026 Uiso 1 1 calc R
C1B C 0.59717(17) 0.23767(10) 0.89079(9) 0.0189(3) Uani 1 1 d .
C2B C 0.59004(17) 0.16617(10) 0.83603(9) 0.0190(3) Uani 1 1 d .
C11B C 0.59089(16) 0.30860(10) 0.87226(9) 0.0192(3) Uani 1 1 d .
C12B C 0.57388(17) 0.30400(10) 0.79703(9) 0.0194(3) Uani 1 1 d .
C13B C 0.56232(17) 0.37353(10) 0.78076(9) 0.0214(4) Uani 1 1 d .
H13C H 0.5476 0.3700 0.7301 0.026 Uiso 1 1 calc R
C14B C 0.57156(17) 0.44618(10) 0.83543(10) 0.0227(4) Uani 1 1 d .
C15B C 0.59616(18) 0.45090(10) 0.91021(10) 0.0222(4) Uani 1 1 d .
H15C H 0.6066 0.5009 0.9490 0.027 Uiso 1 1 calc R
C16B C 0.60534(17) 0.38442(10) 0.92825(9) 0.0211(3) Uani 1 1 d .
H16C H 0.6217 0.3893 0.9793 0.025 Uiso 1 1 calc R
C17B C 0.5531(2) 0.51823(10) 0.81522(10) 0.0284(4) Uani 1 1 d .
H17G H 0.5948 0.5180 0.7731 0.043 Uiso 1 1 calc R
H17H H 0.6010 0.5676 0.8586 0.043 Uiso 1 1 calc R
H17I H 0.4513 0.5158 0.8008 0.043 Uiso 1 1 calc R
C21B C 0.61182(18) 0.24354(9) 0.97060(9) 0.0196(3) Uani 1 1 d .
C22B C 0.73305(18) 0.23302(10) 1.01178(9) 0.0220(4) Uani 1 1 d .
H22C H 0.8086 0.2218 0.9892 0.026 Uiso 1 1 calc R
C23B C 0.74463(19) 0.23878(10) 1.08548(10) 0.0267(4) Uani 1 1 d .
H23C H 0.8284 0.2316 1.1126 0.032 Uiso 1 1 calc R
C24B C 0.6363(2) 0.25485(10) 1.12053(10) 0.0284(4) Uani 1 1 d .
C25B C 0.5145(2) 0.26454(11) 1.07893(10) 0.0279(4) Uani 1 1 d .
H25C H 0.4385 0.2750 1.1014 0.033 Uiso 1 1 calc R
C26B C 0.50228(19) 0.25920(10) 1.00544(10) 0.0238(4) Uani 1 1 d .
H26C H 0.4183 0.2663 0.9783 0.029 Uiso 1 1 calc R
C27B C 0.6512(2) 0.26212(13) 1.20120(11) 0.0427(5) Uani 1 1 d .
H27G H 0.5714 0.2808 1.2184 0.064 Uiso 1 1 calc R
H27H H 0.7411 0.3008 1.2325 0.064 Uiso 1 1 calc R
H27I H 0.6508 0.2095 1.2050 0.064 Uiso 1 1 calc R
C31B C 0.57216(17) 0.15943(10) 0.75840(9) 0.0188(3) Uani 1 1 d .
C32B C 0.56572(17) 0.22789(10) 0.73870(9) 0.0196(3) Uani 1 1 d .
C33B C 0.54903(18) 0.21860(10) 0.66250(9) 0.0224(4) Uani 1 1 d .
H33C H 0.5478 0.2643 0.6488 0.027 Uiso 1 1 calc R
C34B C 0.53456(18) 0.14540(11) 0.60769(10) 0.0243(4) Uani 1 1 d .
H34C H 0.5226 0.1408 0.5568 0.029 Uiso 1 1 calc R
C35B C 0.53749(18) 0.07778(10) 0.62697(9) 0.0234(4) Uani 1 1 d .
H35C H 0.5262 0.0270 0.5891 0.028 Uiso 1 1 calc R
C36B C 0.55678(18) 0.08487(10) 0.70067(9) 0.0219(4) Uani 1 1 d .
H36B H 0.5599 0.0386 0.7132 0.026 Uiso 1 1 calc R
C41B C 0.59960(17) 0.09292(9) 0.85454(9) 0.0192(3) Uani 1 1 d .
C42B C 0.71693(18) 0.06091(10) 0.84737(9) 0.0224(4) Uani 1 1 d .
H42C H 0.7915 0.0865 0.8316 0.027 Uiso 1 1 calc R
C43B C 0.72671(19) -0.00776(10) 0.86281(9) 0.0239(4) Uani 1 1 d .
H43C H 0.8076 -0.0289 0.8577 0.029 Uiso 1 1 calc R
C44B C 0.61792(19) -0.04568(10) 0.88579(9) 0.0246(4) Uani 1 1 d .
H44C H 0.6235 -0.0932 0.8957 0.029 Uiso 1 1 calc R
C45B C 0.50137(19) -0.01376(10) 0.89409(10) 0.0253(4) Uani 1 1 d .
H45C H 0.4278 -0.0389 0.9107 0.030 Uiso 1 1 calc R
C46B C 0.49144(18) 0.05479(10) 0.87821(9) 0.0218(4) Uani 1 1 d .
H46C H 0.4106 0.0759 0.8835 0.026 Uiso 1 1 calc R
Cl1 Cl 0.13989(5) 0.49700(3) 0.71708(2) 0.03328(12) Uani 1 1 d .
Cl2 Cl -0.02619(6) 0.36979(3) 0.57905(3) 0.04211(13) Uani 1 1 d .
Cl3 Cl -0.14972(5) 0.41720(3) 0.70582(3) 0.04523(14) Uani 1 1 d .
C1S C 0.0078(2) 0.40569(11) 0.67753(10) 0.0312(4) Uani 1 1 d .
H1SA H 0.0440 0.3653 0.6957 0.037 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0211(9) 0.0170(8) 0.0128(7) 0.0054(6) 0.0047(6) 0.0051(6)
C2 0.0195(9) 0.0161(8) 0.0134(7) 0.0052(6) 0.0035(6) 0.0040(6)
C11 0.0222(9) 0.0168(8) 0.0144(8) 0.0059(6) 0.0057(6) 0.0046(6)
C12 0.0229(9) 0.0176(8) 0.0145(8) 0.0057(6) 0.0054(6) 0.0051(6)
C13 0.0253(9) 0.0184(8) 0.0177(8) 0.0069(7) 0.0065(6) 0.0085(7)
C14 0.0259(9) 0.0168(8) 0.0162(8) 0.0064(6) 0.0066(6) 0.0037(6)
C15 0.0208(9) 0.0208(9) 0.0249(9) 0.0083(7) 0.0096(7) 0.0024(7)
C16 0.0220(9) 0.0209(9) 0.0247(9) 0.0099(7) 0.0093(7) 0.0083(7)
C17 0.0282(10) 0.0199(9) 0.0236(9) 0.0091(7) 0.0063(7) 0.0044(7)
C21 0.0185(8) 0.0137(8) 0.0222(8) 0.0087(6) 0.0075(6) 0.0012(6)
C22 0.0252(9) 0.0204(8) 0.0182(8) 0.0071(7) 0.0071(7) 0.0061(7)
C23 0.0217(9) 0.0262(9) 0.0223(9) 0.0134(7) 0.0044(7) 0.0056(7)
C24 0.0196(9) 0.0179(8) 0.0295(9) 0.0134(7) 0.0105(7) 0.0050(6)
C25 0.0235(9) 0.0171(8) 0.0229(9) 0.0049(7) 0.0097(7) 0.0039(6)
C26 0.0177(9) 0.0191(8) 0.0199(8) 0.0077(7) 0.0038(6) 0.0029(6)
C27 0.0269(10) 0.0259(9) 0.0367(10) 0.0151(8) 0.0122(8) 0.0111(7)
C31 0.0217(9) 0.0174(8) 0.0136(8) 0.0061(6) 0.0045(6) 0.0053(6)
C32 0.0226(9) 0.0195(8) 0.0146(8) 0.0061(6) 0.0051(6) 0.0059(6)
C33 0.0263(10) 0.0212(9) 0.0332(10) 0.0153(8) 0.0095(7) 0.0088(7)
C34 0.0242(10) 0.0285(10) 0.0415(11) 0.0202(8) 0.0129(8) 0.0142(7)
C35 0.0193(9) 0.0288(9) 0.0327(10) 0.0157(8) 0.0090(7) 0.0065(7)
C36 0.0227(9) 0.0184(8) 0.0228(9) 0.0101(7) 0.0068(7) 0.0049(7)
C41 0.0134(8) 0.0182(8) 0.0223(8) 0.0092(7) 0.0037(6) 0.0057(6)
C42 0.0207(9) 0.0218(9) 0.0201(8) 0.0073(7) 0.0054(6) 0.0054(7)
C43 0.0205(9) 0.0158(8) 0.0286(9) 0.0045(7) 0.0049(7) 0.0044(6)
C44 0.0216(9) 0.0179(8) 0.0353(10) 0.0139(7) 0.0061(7) 0.0048(7)
C45 0.0298(10) 0.0252(9) 0.0248(9) 0.0142(7) 0.0083(7) 0.0065(7)
C46 0.0265(9) 0.0187(8) 0.0198(8) 0.0070(7) 0.0053(7) 0.0053(7)
C1A 0.0131(8) 0.0186(8) 0.0206(8) 0.0094(7) 0.0041(6) 0.0038(6)
C2A 0.0139(8) 0.0202(8) 0.0202(8) 0.0095(7) 0.0044(6) 0.0038(6)
C11A 0.0136(8) 0.0202(8) 0.0206(8) 0.0093(7) 0.0050(6) 0.0050(6)
C12A 0.0135(8) 0.0209(8) 0.0199(8) 0.0091(7) 0.0035(6) 0.0035(6)
C13A 0.0190(9) 0.0198(8) 0.0234(9) 0.0110(7) 0.0053(6) 0.0048(6)
C14A 0.0187(9) 0.0249(9) 0.0206(9) 0.0095(7) 0.0042(6) 0.0042(7)
C15A 0.0226(9) 0.0220(9) 0.0193(8) 0.0059(7) 0.0061(7) 0.0056(7)
C16A 0.0201(9) 0.0191(8) 0.0231(9) 0.0094(7) 0.0061(7) 0.0055(6)
C17A 0.0373(11) 0.0260(9) 0.0222(9) 0.0108(7) 0.0070(8) 0.0068(8)
C21A 0.0212(9) 0.0180(8) 0.0142(8) 0.0062(6) 0.0033(6) 0.0045(6)
C22A 0.0218(9) 0.0215(9) 0.0199(8) 0.0092(7) 0.0062(6) 0.0045(7)
C23A 0.0249(9) 0.0248(9) 0.0231(9) 0.0105(7) 0.0089(7) 0.0121(7)
C24A 0.0282(9) 0.0184(8) 0.0156(8) 0.0072(6) 0.0055(6) 0.0077(7)
C25A 0.0231(9) 0.0207(8) 0.0205(8) 0.0096(7) 0.0072(7) 0.0027(7)
C26A 0.0192(9) 0.0217(8) 0.0207(8) 0.0084(7) 0.0064(6) 0.0070(6)
C27A 0.0363(11) 0.0219(9) 0.0266(9) 0.0119(7) 0.0114(8) 0.0111(7)
C31A 0.0136(8) 0.0191(8) 0.0203(8) 0.0077(7) 0.0032(6) 0.0042(6)
C32A 0.0203(9) 0.0230(9) 0.0194(8) 0.0084(7) 0.0049(6) 0.0055(7)
C33A 0.0219(9) 0.0195(8) 0.0239(9) 0.0048(7) 0.0052(7) 0.0049(7)
C34A 0.0217(9) 0.0175(8) 0.0311(10) 0.0110(7) 0.0070(7) 0.0059(7)
C35A 0.0200(9) 0.0218(9) 0.0225(9) 0.0114(7) 0.0046(6) 0.0047(6)
C36A 0.0130(8) 0.0191(8) 0.0215(8) 0.0089(7) 0.0034(6) 0.0035(6)
C41A 0.0207(9) 0.0121(7) 0.0189(8) 0.0057(6) 0.0038(6) 0.0031(6)
C42A 0.0191(9) 0.0148(8) 0.0211(8) 0.0050(6) 0.0055(6) 0.0027(6)
C43A 0.0225(9) 0.0194(8) 0.0213(8) 0.0081(7) 0.0007(7) 0.0047(7)
C44A 0.0298(10) 0.0239(9) 0.0179(8) 0.0088(7) 0.0059(7) 0.0049(7)
C45A 0.0242(10) 0.0286(9) 0.0220(9) 0.0091(7) 0.0097(7) 0.0054(7)
C46A 0.0197(9) 0.0228(9) 0.0228(9) 0.0083(7) 0.0052(7) 0.0065(7)
C1B 0.0128(8) 0.0230(9) 0.0223(8) 0.0110(7) 0.0039(6) 0.0035(6)
C2B 0.0129(8) 0.0225(9) 0.0245(9) 0.0123(7) 0.0046(6) 0.0044(6)
C11B 0.0111(8) 0.0230(9) 0.0253(9) 0.0115(7) 0.0043(6) 0.0041(6)
C12B 0.0125(8) 0.0222(9) 0.0249(9) 0.0108(7) 0.0042(6) 0.0040(6)
C13B 0.0182(9) 0.0246(9) 0.0240(9) 0.0137(7) 0.0047(7) 0.0034(7)
C14B 0.0156(9) 0.0229(9) 0.0314(10) 0.0139(7) 0.0045(7) 0.0034(7)
C15B 0.0183(9) 0.0192(8) 0.0275(9) 0.0074(7) 0.0047(7) 0.0037(6)
C16B 0.0171(9) 0.0243(9) 0.0217(9) 0.0099(7) 0.0033(6) 0.0036(7)
C17B 0.0298(10) 0.0227(9) 0.0329(10) 0.0127(8) 0.0053(8) 0.0049(7)
C21B 0.0211(9) 0.0158(8) 0.0212(8) 0.0080(7) 0.0043(6) 0.0018(6)
C22B 0.0207(9) 0.0190(8) 0.0263(9) 0.0100(7) 0.0040(7) 0.0034(7)
C23B 0.0278(10) 0.0226(9) 0.0265(9) 0.0129(7) -0.0025(7) 0.0001(7)
C24B 0.0372(11) 0.0224(9) 0.0240(9) 0.0117(7) 0.0050(8) 0.0001(7)
C25B 0.0321(11) 0.0261(9) 0.0271(10) 0.0107(8) 0.0122(8) 0.0045(8)
C26B 0.0228(9) 0.0245(9) 0.0249(9) 0.0111(7) 0.0046(7) 0.0055(7)
C27B 0.0538(14) 0.0454(13) 0.0258(11) 0.0166(9) 0.0075(9) 0.0008(10)
C31B 0.0122(8) 0.0218(8) 0.0237(9) 0.0101(7) 0.0047(6) 0.0040(6)
C32B 0.0139(8) 0.0236(9) 0.0242(9) 0.0121(7) 0.0061(6) 0.0042(6)
C33B 0.0201(9) 0.0258(9) 0.0265(9) 0.0146(7) 0.0078(7) 0.0069(7)
C34B 0.0225(9) 0.0318(10) 0.0217(9) 0.0123(7) 0.0074(7) 0.0073(7)
C35B 0.0211(9) 0.0241(9) 0.0237(9) 0.0065(7) 0.0068(7) 0.0058(7)
C36B 0.0199(9) 0.0219(9) 0.0274(9) 0.0123(7) 0.0070(7) 0.0062(7)
C41B 0.0198(9) 0.0195(8) 0.0166(8) 0.0064(6) 0.0024(6) 0.0035(6)
C42B 0.0221(9) 0.0237(9) 0.0235(9) 0.0117(7) 0.0057(7) 0.0051(7)
C43B 0.0250(10) 0.0240(9) 0.0247(9) 0.0099(7) 0.0044(7) 0.0105(7)
C44B 0.0288(10) 0.0200(9) 0.0247(9) 0.0114(7) 0.0014(7) 0.0052(7)
C45B 0.0236(9) 0.0259(9) 0.0275(9) 0.0139(7) 0.0054(7) 0.0021(7)
C46B 0.0209(9) 0.0225(9) 0.0229(9) 0.0094(7) 0.0048(7) 0.0063(7)
Cl1 0.0352(3) 0.0337(2) 0.0276(2) 0.01268(19) 0.00691(18) -0.00148(19)
Cl2 0.0490(3) 0.0384(3) 0.0296(3) 0.0080(2) 0.0016(2) 0.0046(2)
Cl3 0.0301(3) 0.0587(3) 0.0498(3) 0.0253(3) 0.0125(2) 0.0053(2)
C1S 0.0342(11) 0.0291(10) 0.0311(10) 0.0154(8) 0.0056(8) 0.0043(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C11 120.59(14)
C2 C1 C21 119.66(14)
C11 C1 C21 119.74(14)
C1 C2 C31 120.30(14)
C1 C2 C41 120.95(14)
C31 C2 C41 118.73(14)
C16 C11 C12 118.42(14)
C16 C11 C1 121.32(14)
C12 C11 C1 120.23(14)
C13 C12 C11 118.50(15)
C13 C12 C32 122.55(15)
C11 C12 C32 118.94(14)
C14 C13 C12 122.60(15)
C14 C13 H13A 118.7
C12 C13 H13A 118.7
C13 C14 C15 118.14(15)
C13 C14 C17 121.69(15)
C15 C14 C17 120.17(15)
C16 C15 C14 121.00(15)
C16 C15 H15A 119.5
C14 C15 H15A 119.5
C15 C16 C11 121.29(15)
C15 C16 H16A 119.4
C11 C16 H16A 119.4
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C22 C21 C26 117.75(15)
C22 C21 C1 122.34(14)
C26 C21 C1 119.88(14)
C21 C22 C23 121.06(15)
C21 C22 H22A 119.5
C23 C22 H22A 119.5
C24 C23 C22 121.15(15)
C24 C23 H23A 119.4
C22 C23 H23A 119.4
C23 C24 C25 117.92(15)
C23 C24 C27 121.00(15)
C25 C24 C27 121.08(15)
C26 C25 C24 120.92(15)
C26 C25 H25A 119.5
C24 C25 H25A 119.5
C25 C26 C21 121.14(15)
C25 C26 H26A 119.4
C21 C26 H26A 119.4
C24 C27 H27A 109.5
C24 C27 H27B 109.5
H27A C27 H27B 109.5
C24 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C32 C31 C36 119.08(14)
C32 C31 C2 120.20(14)
C36 C31 C2 120.69(14)
C31 C32 C33 118.26(15)
C31 C32 C12 119.59(14)
C33 C32 C12 122.14(15)
C34 C33 C32 121.22(16)
C34 C33 H33A 119.4
C32 C33 H33A 119.4
C33 C34 C35 120.57(16)
C33 C34 H34A 119.7
C35 C34 H34A 119.7
C36 C35 C34 119.55(16)
C36 C35 H35A 120.2
C34 C35 H35A 120.2
C35 C36 C31 121.32(15)
C35 C36 H36A 119.3
C31 C36 H36A 119.3
C46 C41 C42 118.35(15)
C46 C41 C2 119.96(14)
C42 C41 C2 121.69(14)
C43 C42 C41 120.59(15)
C43 C42 H42A 119.7
C41 C42 H42A 119.7
C44 C43 C42 120.52(15)
C44 C43 H43A 119.7
C42 C43 H43A 119.7
C43 C44 C45 119.58(15)
C43 C44 H44A 120.2
C45 C44 H44A 120.2
C46 C45 C44 119.93(16)
C46 C45 H45A 120.0
C44 C45 H45A 120.0
C45 C46 C41 121.01(15)
C45 C46 H46A 119.5
C41 C46 H46A 119.5
C2A C1A C11A 120.59(14)
C2A C1A C21A 120.59(14)
C11A C1A C21A 118.80(14)
C1A C2A C31A 120.67(14)
C1A C2A C41A 119.14(14)
C31A C2A C41A 120.18(14)
C16A C11A C12A 118.40(14)
C16A C11A C1A 121.34(14)
C12A C11A C1A 120.26(14)
C13A C12A C11A 118.42(14)
C13A C12A C36A 122.55(14)
C11A C12A C36A 119.02(14)
C14A C13A C12A 122.66(15)
C14A C13A H13B 118.7
C12A C13A H13B 118.7
C13A C14A C15A 118.15(15)
C13A C14A C17A 121.95(15)
C15A C14A C17A 119.89(15)
C16A C15A C14A 121.02(15)
C16A C15A H15B 119.5
C14A C15A H15B 119.5
C15A C16A C11A 121.31(15)
C15A C16A H16B 119.3
C11A C16A H16B 119.3
C14A C17A H17D 109.5
C14A C17A H17E 109.5
H17D C17A H17E 109.5
C14A C17A H17F 109.5
H17D C17A H17F 109.5
H17E C17A H17F 109.5
C22A C21A C26A 118.35(15)
C22A C21A C1A 121.18(14)
C26A C21A C1A 120.46(14)
C23A C22A C21A 120.89(15)
C23A C22A H22B 119.6
C21A C22A H22B 119.6
C22A C23A C24A 121.02(16)
C22A C23A H23B 119.5
C24A C23A H23B 119.5
C25A C24A C23A 117.63(15)
C25A C24A C27A 121.56(15)
C23A C24A C27A 120.78(15)
C26A C25A C24A 121.49(15)
C26A C25A H25B 119.3
C24A C25A H25B 119.3
C25A C26A C21A 120.59(15)
C25A C26A H26B 119.7
C21A C26A H26B 119.7
C24A C27A H27D 109.5
C24A C27A H27E 109.5
H27D C27A H27E 109.5
C24A C27A H27F 109.5
H27D C27A H27F 109.5
H27E C27A H27F 109.5
C32A C31A C36A 118.95(14)
C32A C31A C2A 121.11(14)
C36A C31A C2A 119.93(14)
C33A C32A C31A 121.17(15)
C33A C32A H32A 119.4
C31A C32A H32A 119.4
C32A C33A C34A 119.94(15)
C32A C33A H33B 120.0
C34A C33A H33B 120.0
C35A C34A C33A 120.04(15)
C35A C34A H34B 120.0
C33A C34A H34B 120.0
C34A C35A C36A 121.65(15)
C34A C35A H35B 119.2
C36A C35A H35B 119.2
C35A C36A C31A 118.22(14)
C35A C36A C12A 122.28(14)
C31A C36A C12A 119.49(14)
C42A C41A C46A 118.67(15)
C42A C41A C2A 120.51(14)
C46A C41A C2A 120.79(14)
C43A C42A C41A 120.60(15)
C43A C42A H42B 119.7
C41A C42A H42B 119.7
C44A C43A C42A 120.19(15)
C44A C43A H43B 119.9
C42A C43A H43B 119.9
C45A C44A C43A 119.56(15)
C45A C44A H44B 120.2
C43A C44A H44B 120.2
C44A C45A C46A 120.44(16)
C44A C45A H45B 119.8
C46A C45A H45B 119.8
C45A C46A C41A 120.53(16)
C45A C46A H46B 119.7
C41A C46A H46B 119.7
C2B C1B C11B 120.34(15)
C2B C1B C21B 120.34(14)
C11B C1B C21B 119.32(14)
C1B C2B C31B 120.70(15)
C1B C2B C41B 120.97(14)
C31B C2B C41B 118.33(14)
C12B C11B C16B 118.05(15)
C12B C11B C1B 120.27(15)
C16B C11B C1B 121.66(15)
C13B C12B C11B 118.60(15)
C13B C12B C32B 121.97(15)
C11B C12B C32B 119.41(14)
C14B C13B C12B 122.64(15)
C14B C13B H13C 118.7
C12B C13B H13C 118.7
C13B C14B C15B 118.08(15)
C13B C14B C17B 120.89(16)
C15B C14B C17B 121.02(15)
C16B C15B C14B 121.09(15)
C16B C15B H15C 119.5
C14B C15B H15C 119.5
C15B C16B C11B 121.40(15)
C15B C16B H16C 119.3
C11B C16B H16C 119.3
C14B C17B H17G 109.5
C14B C17B H17H 109.5
H17G C17B H17H 109.5
C14B C17B H17I 109.5
H17G C17B H17I 109.5
H17H C17B H17I 109.5
C22B C21B C26B 118.11(15)
C22B C21B C1B 121.51(15)
C26B C21B C1B 120.38(15)
C23B C22B C21B 120.63(16)
C23B C22B H22C 119.7
C21B C22B H22C 119.7
C22B C23B C24B 121.45(16)
C22B C23B H23C 119.3
C24B C23B H23C 119.3
C23B C24B C25B 117.78(16)
C23B C24B C27B 120.89(18)
C25B C24B C27B 121.33(18)
C26B C25B C24B 121.14(17)
C26B C25B H25C 119.4
C24B C25B H25C 119.4
C25B C26B C21B 120.88(16)
C25B C26B H26C 119.6
C21B C26B H26C 119.6
C24B C27B H27G 109.5
C24B C27B H27H 109.5
H27G C27B H27H 109.5
C24B C27B H27I 109.5
H27G C27B H27I 109.5
H27H C27B H27I 109.5
C36B C31B C32B 118.59(15)
C36B C31B C2B 121.27(15)
C32B C31B C2B 120.11(15)
C33B C32B C31B 118.14(15)
C33B C32B C12B 122.72(15)
C31B C32B C12B 119.13(14)
C34B C33B C32B 121.89(16)
C34B C33B H33C 119.1
C32B C33B H33C 119.1
C33B C34B C35B 119.83(16)
C33B C34B H34C 120.1
C35B C34B H34C 120.1
C36B C35B C34B 119.92(16)
C36B C35B H35C 120.0
C34B C35B H35C 120.0
C35B C36B C31B 121.59(15)
C35B C36B H36B 119.2
C31B C36B H36B 119.2
C42B C41B C46B 118.64(15)
C42B C41B C2B 120.06(14)
C46B C41B C2B 121.30(14)
C43B C42B C41B 121.03(16)
C43B C42B H42C 119.5
C41B C42B H42C 119.5
C42B C43B C44B 119.92(16)
C42B C43B H43C 120.0
C44B C43B H43C 120.0
C45B C44B C43B 119.58(16)
C45B C44B H44C 120.2
C43B C44B H44C 120.2
C44B C45B C46B 120.40(16)
C44B C45B H45C 119.8
C46B C45B H45C 119.8
C45B C46B C41B 120.42(16)
C45B C46B H46C 119.8
C41B C46B H46C 119.8
Cl1 C1S Cl2 110.13(10)
Cl1 C1S Cl3 110.92(11)
Cl2 C1S Cl3 110.70(11)
Cl1 C1S H1SA 108.3
Cl2 C1S H1SA 108.3
Cl3 C1S H1SA 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.366(2)
C1 C11 1.451(2)
C1 C21 1.500(2)
C2 C31 1.450(2)
C2 C41 1.498(2)
C11 C16 1.413(2)
C11 C12 1.418(2)
C12 C13 1.411(2)
C12 C32 1.453(2)
C13 C14 1.374(2)
C13 H13A 0.9500
C14 C15 1.409(2)
C14 C17 1.505(2)
C15 C16 1.370(2)
C15 H15A 0.9500
C16 H16A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C21 C22 1.389(2)
C21 C26 1.398(2)
C22 C23 1.392(2)
C22 H22A 0.9500
C23 C24 1.390(2)
C23 H23A 0.9500
C24 C25 1.395(2)
C24 C27 1.511(2)
C25 C26 1.388(2)
C25 H25A 0.9500
C26 H26A 0.9500
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C31 C32 1.414(2)
C31 C36 1.416(2)
C32 C33 1.416(2)
C33 C34 1.372(2)
C33 H33A 0.9500
C34 C35 1.399(2)
C34 H34A 0.9500
C35 C36 1.371(2)
C35 H35A 0.9500
C36 H36A 0.9500
C41 C46 1.392(2)
C41 C42 1.396(2)
C42 C43 1.384(2)
C42 H42A 0.9500
C43 C44 1.381(2)
C43 H43A 0.9500
C44 C45 1.387(2)
C44 H44A 0.9500
C45 C46 1.386(2)
C45 H45A 0.9500
C46 H46A 0.9500
C1A C2A 1.367(2)
C1A C11A 1.448(2)
C1A C21A 1.498(2)
C2A C31A 1.449(2)
C2A C41A 1.498(2)
C11A C16A 1.414(2)
C11A C12A 1.418(2)
C12A C13A 1.411(2)
C12A C36A 1.457(2)
C13A C14A 1.378(2)
C13A H13B 0.9500
C14A C15A 1.404(2)
C14A C17A 1.505(2)
C15A C16A 1.372(2)
C15A H15B 0.9500
C16A H16B 0.9500
C17A H17D 0.9800
C17A H17E 0.9800
C17A H17F 0.9800
C21A C22A 1.391(2)
C21A C26A 1.392(2)
C22A C23A 1.384(2)
C22A H22B 0.9500
C23A C24A 1.400(2)
C23A H23B 0.9500
C24A C25A 1.389(2)
C24A C27A 1.499(2)
C25A C26A 1.386(2)
C25A H25B 0.9500
C26A H26B 0.9500
C27A H27D 0.9800
C27A H27E 0.9800
C27A H27F 0.9800
C31A C32A 1.417(2)
C31A C36A 1.418(2)
C32A C33A 1.375(2)
C32A H32A 0.9500
C33A C34A 1.398(2)
C33A H33B 0.9500
C34A C35A 1.374(2)
C34A H34B 0.9500
C35A C36A 1.413(2)
C35A H35B 0.9500
C41A C42A 1.394(2)
C41A C46A 1.397(2)
C42A C43A 1.391(2)
C42A H42B 0.9500
C43A C44A 1.389(2)
C43A H43B 0.9500
C44A C45A 1.384(2)
C44A H44B 0.9500
C45A C46A 1.388(2)
C45A H45B 0.9500
C46A H46B 0.9500
C1B C2B 1.370(2)
C1B C11B 1.452(2)
C1B C21B 1.501(2)
C2B C31B 1.452(2)
C2B C41B 1.498(2)
C11B C12B 1.417(2)
C11B C16B 1.418(2)
C12B C13B 1.414(2)
C12B C32B 1.457(2)
C13B C14B 1.378(2)
C13B H13C 0.9500
C14B C15B 1.403(2)
C14B C17B 1.512(2)
C15B C16B 1.373(2)
C15B H15C 0.9500
C16B H16C 0.9500
C17B H17G 0.9800
C17B H17H 0.9800
C17B H17I 0.9800
C21B C22B 1.392(2)
C21B C26B 1.398(2)
C22B C23B 1.387(2)
C22B H22C 0.9500
C23B C24B 1.391(3)
C23B H23C 0.9500
C24B C25B 1.393(3)
C24B C27B 1.511(2)
C25B C26B 1.384(2)
C25B H25C 0.9500
C26B H26C 0.9500
C27B H27G 0.9800
C27B H27H 0.9800
C27B H27I 0.9800
C31B C36B 1.416(2)
C31B C32B 1.421(2)
C32B C33B 1.413(2)
C33B C34B 1.375(2)
C33B H33C 0.9500
C34B C35B 1.397(2)
C34B H34C 0.9500
C35B C36B 1.373(2)
C35B H35C 0.9500
C36B H36B 0.9500
C41B C42B 1.391(2)
C41B C46B 1.397(2)
C42B C43B 1.387(2)
C42B H42C 0.9500
C43B C44B 1.391(2)
C43B H43C 0.9500
C44B C45B 1.386(3)
C44B H44C 0.9500
C45B C46B 1.389(2)
C45B H45C 0.9500
C46B H46C 0.9500
Cl1 C1S 1.7591(19)
Cl2 C1S 1.7608(19)
Cl3 C1S 1.762(2)
C1S H1SA 1.0000
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C11 C1 C2 C31 4.1(2)
C21 C1 C2 C31 -175.17(13)
C11 C1 C2 C41 -174.35(14)
C21 C1 C2 C41 6.4(2)
C2 C1 C11 C16 174.06(15)
C21 C1 C11 C16 -6.7(2)
C2 C1 C11 C12 -4.0(2)
C21 C1 C11 C12 175.27(14)
C16 C11 C12 C13 2.0(2)
C1 C11 C12 C13 -179.92(14)
C16 C11 C12 C32 -177.11(14)
C1 C11 C12 C32 1.0(2)
C11 C12 C13 C14 -1.3(2)
C32 C12 C13 C14 177.81(15)
C12 C13 C14 C15 -0.7(2)
C12 C13 C14 C17 180.00(15)
C13 C14 C15 C16 2.0(2)
C17 C14 C15 C16 -178.71(15)
C14 C15 C16 C11 -1.3(2)
C12 C11 C16 C15 -0.8(2)
C1 C11 C16 C15 -178.85(15)
C2 C1 C21 C22 -92.74(19)
C11 C1 C21 C22 88.02(19)
C2 C1 C21 C26 84.90(19)
C11 C1 C21 C26 -94.35(18)
C26 C21 C22 C23 -2.3(2)
C1 C21 C22 C23 175.35(15)
C21 C22 C23 C24 0.3(3)
C22 C23 C24 C25 1.9(2)
C22 C23 C24 C27 -177.83(15)
C23 C24 C25 C26 -1.9(2)
C27 C24 C25 C26 177.78(15)
C24 C25 C26 C21 -0.2(2)
C22 C21 C26 C25 2.3(2)
C1 C21 C26 C25 -175.46(14)
C1 C2 C31 C32 -1.3(2)
C41 C2 C31 C32 177.20(14)
C1 C2 C31 C36 176.70(14)
C41 C2 C31 C36 -4.8(2)
C36 C31 C32 C33 -0.3(2)
C2 C31 C32 C33 177.70(14)
C36 C31 C32 C12 -179.69(14)
C2 C31 C32 C12 -1.7(2)
C13 C12 C32 C31 -177.29(14)
C11 C12 C32 C31 1.8(2)
C13 C12 C32 C33 3.3(2)
C11 C12 C32 C33 -177.60(15)
C31 C32 C33 C34 -0.3(2)
C12 C32 C33 C34 179.06(16)
C32 C33 C34 C35 0.3(3)
C33 C34 C35 C36 0.4(3)
C34 C35 C36 C31 -1.0(3)
C32 C31 C36 C35 1.0(2)
C2 C31 C36 C35 -177.00(15)
C1 C2 C41 C46 101.81(18)
C31 C2 C41 C46 -76.64(19)
C1 C2 C41 C42 -78.6(2)
C31 C2 C41 C42 102.95(18)
C46 C41 C42 C43 -1.1(2)
C2 C41 C42 C43 179.30(15)
C41 C42 C43 C44 0.9(2)
C42 C43 C44 C45 -0.1(3)
C43 C44 C45 C46 -0.5(3)
C44 C45 C46 C41 0.3(3)
C42 C41 C46 C45 0.5(2)
C2 C41 C46 C45 -179.85(15)
C11A C1A C2A C31A 0.1(2)
C21A C1A C2A C31A 178.49(14)
C11A C1A C2A C41A 179.19(14)
C21A C1A C2A C41A -2.4(2)
C2A C1A C11A C16A 177.29(15)
C21A C1A C11A C16A -1.2(2)
C2A C1A C11A C12A -1.9(2)
C21A C1A C11A C12A 179.67(14)
C16A C11A C12A C13A 2.3(2)
C1A C11A C12A C13A -178.48(14)
C16A C11A C12A C36A -176.65(14)
C1A C11A C12A C36A 2.5(2)
C11A C12A C13A C14A -1.9(2)
C36A C12A C13A C14A 177.00(15)
C12A C13A C14A C15A 0.6(2)
C12A C13A C14A C17A -178.45(16)
C13A C14A C15A C16A 0.4(2)
C17A C14A C15A C16A 179.42(16)
C14A C15A C16A C11A 0.1(3)
C12A C11A C16A C15A -1.5(2)
C1A C11A C16A C15A 179.35(15)
C2A C1A C21A C22A 108.73(18)
C11A C1A C21A C22A -72.8(2)
C2A C1A C21A C26A -72.1(2)
C11A C1A C21A C26A 106.37(18)
C26A C21A C22A C23A -1.3(2)
C1A C21A C22A C23A 177.95(15)
C21A C22A C23A C24A -0.4(3)
C22A C23A C24A C25A 1.7(2)
C22A C23A C24A C27A -176.08(15)
C23A C24A C25A C26A -1.5(2)
C27A C24A C25A C26A 176.31(15)
C24A C25A C26A C21A -0.1(2)
C22A C21A C26A C25A 1.5(2)
C1A C21A C26A C25A -177.70(14)
C1A C2A C31A C32A 179.55(15)
C41A C2A C31A C32A 0.4(2)
C1A C2A C31A C36A 1.0(2)
C41A C2A C31A C36A -178.10(14)
C36A C31A C32A C33A -1.4(2)
C2A C31A C32A C33A -179.94(15)
C31A C32A C33A C34A -0.2(3)
C32A C33A C34A C35A 1.2(3)
C33A C34A C35A C36A -0.6(3)
C34A C35A C36A C31A -1.0(2)
C34A C35A C36A C12A 179.88(15)
C32A C31A C36A C35A 1.9(2)
C2A C31A C36A C35A -179.50(15)
C32A C31A C36A C12A -178.88(15)
C2A C31A C36A C12A -0.3(2)
C13A C12A C36A C35A -1.2(2)
C11A C12A C36A C35A 177.70(15)
C13A C12A C36A C31A 179.62(14)
C11A C12A C36A C31A -1.4(2)
C1A C2A C41A C42A -67.7(2)
C31A C2A C41A C42A 111.47(17)
C1A C2A C41A C46A 110.30(18)
C31A C2A C41A C46A -70.6(2)
C46A C41A C42A C43A 0.1(2)
C2A C41A C42A C43A 178.12(14)
C41A C42A C43A C44A -0.5(2)
C42A C43A C44A C45A 0.1(2)
C43A C44A C45A C46A 0.5(3)
C44A C45A C46A C41A -0.8(3)
C42A C41A C46A C45A 0.5(2)
C2A C41A C46A C45A -177.48(15)
C11B C1B C2B C31B -1.7(2)
C21B C1B C2B C31B 178.40(14)
C11B C1B C2B C41B 178.64(14)
C21B C1B C2B C41B -1.2(2)
C2B C1B C11B C12B 1.5(2)
C21B C1B C11B C12B -178.59(14)
C2B C1B C11B C16B -176.71(15)
C21B C1B C11B C16B 3.2(2)
C16B C11B C12B C13B -4.3(2)
C1B C11B C12B C13B 177.42(14)
C16B C11B C12B C32B 177.03(14)
C1B C11B C12B C32B -1.3(2)
C11B C12B C13B C14B 2.2(2)
C32B C12B C13B C14B -179.19(15)
C12B C13B C14B C15B 1.2(2)
C12B C13B C14B C17B -177.67(15)
C13B C14B C15B C16B -2.5(2)
C17B C14B C15B C16B 176.45(16)
C14B C15B C16B C11B 0.2(3)
C12B C11B C16B C15B 3.2(2)
C1B C11B C16B C15B -178.54(15)
C2B C1B C21B C22B 65.1(2)
C11B C1B C21B C22B -114.76(17)
C2B C1B C21B C26B -114.32(18)
C11B C1B C21B C26B 65.8(2)
C26B C21B C22B C23B -0.6(2)
C1B C21B C22B C23B 179.92(15)
C21B C22B C23B C24B 0.2(3)
C22B C23B C24B C25B 0.4(3)
C22B C23B C24B C27B -179.13(17)
C23B C24B C25B C26B -0.7(3)
C27B C24B C25B C26B 178.88(17)
C24B C25B C26B C21B 0.3(3)
C22B C21B C26B C25B 0.4(2)
C1B C21B C26B C25B 179.83(15)
C1B C2B C31B C36B -176.49(15)
C41B C2B C31B C36B 3.2(2)
C1B C2B C31B C32B 1.7(2)
C41B C2B C31B C32B -178.64(14)
C36B C31B C32B C33B -2.1(2)
C2B C31B C32B C33B 179.65(14)
C36B C31B C32B C12B 176.80(14)
C2B C31B C32B C12B -1.4(2)
C13B C12B C32B C33B 1.5(2)
C11B C12B C32B C33B -179.89(15)
C13B C12B C32B C31B -177.39(15)
C11B C12B C32B C31B 1.3(2)
C31B C32B C33B C34B 2.1(2)
C12B C32B C33B C34B -176.77(16)
C32B C33B C34B C35B -0.6(3)
C33B C34B C35B C36B -0.9(3)
C34B C35B C36B C31B 0.8(2)
C32B C31B C36B C35B 0.7(2)
C2B C31B C36B C35B 178.92(15)
C1B C2B C41B C42B -112.83(18)
C31B C2B C41B C42B 67.5(2)
C1B C2B C41B C46B 68.0(2)
C31B C2B C41B C46B -111.65(18)
C46B C41B C42B C43B 0.4(2)
C2B C41B C42B C43B -178.76(15)
C41B C42B C43B C44B 0.1(3)
C42B C43B C44B C45B -0.9(3)
C43B C44B C45B C46B 1.3(3)
C44B C45B C46B C41B -0.8(3)
C42B C41B C46B C45B -0.1(2)
C2B C41B C46B C45B 179.08(15)
|
1502014.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502014.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502014
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C26 H16 Br2'
_chemical_formula_weight 488.21
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 79.5680(10)
_cell_angle_beta 77.8540(10)
_cell_angle_gamma 76.2330(10)
_cell_formula_units_Z 2
_cell_length_a 9.6702(2)
_cell_length_b 9.6964(2)
_cell_length_c 11.0895(2)
_cell_measurement_reflns_used 6364
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 67
_cell_measurement_theta_min 4
_cell_volume 977.90(3)
_computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection 'APEX2-2009.5-1 (Bruker, 2009)'
_computing_data_reduction 'SADABS-2008/1 (Bruker, 2008)'
_computing_molecular_graphics 'XP v5.1 (Bruker, 1998)'
_computing_publication_material 'XCIF-2008/2 (Bruker, 2008)'
_computing_structure_refinement 'SHELXL-2008/4(Bruker, 2008)'
_computing_structure_solution 'XS/SHELXTL-2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type 'Bruker APEX2 CCD detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0190
_diffrn_reflns_av_sigmaI/netI 0.0186
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 8064
_diffrn_reflns_theta_full 67.86
_diffrn_reflns_theta_max 67.86
_diffrn_reflns_theta_min 4.12
_exptl_absorpt_coefficient_mu 5.307
_exptl_absorpt_correction_T_max 0.4197
_exptl_absorpt_correction_T_min 0.1491
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
;
Numerical (based on real shape of the crystal) absorption
correction followed by:
SADABS. Program for empirical absorption correction of
area-detector data. University of Goetingen. Germany.
Sheldrick, G. M. 1996
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.658
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 484
_exptl_crystal_size_max 0.58
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.413
_refine_diff_density_min -0.281
_refine_diff_density_rms 0.060
_refine_ls_extinction_coef 0.00261(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.002
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 254
_refine_ls_number_reflns 3317
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.002
_refine_ls_R_factor_all 0.0238
_refine_ls_R_factor_gt 0.0234
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+1.0913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0625
_refine_ls_wR_factor_ref 0.0628
_reflns_number_gt 3258
_reflns_number_total 3317
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_004.cif
_cod_data_source_block raj16ha
_cod_database_code 1502014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.39121(3) -0.01403(2) 0.21347(2) 0.02337(10) Uani 1 1 d .
Br2 Br 0.39924(2) 0.72552(3) -0.051163(19) 0.02387(10) Uani 1 1 d .
C1 C 0.2400(2) 0.4415(2) 0.57022(19) 0.0147(4) Uani 1 1 d .
C2 C 0.2276(2) 0.5821(2) 0.51837(19) 0.0146(4) Uani 1 1 d .
C11 C 0.2784(2) 0.3282(2) 0.48663(18) 0.0150(4) Uani 1 1 d .
C12 C 0.4156(2) 0.2382(2) 0.4701(2) 0.0189(4) Uani 1 1 d .
H12A H 0.4853 0.2454 0.5162 0.023 Uiso 1 1 calc R
C13 C 0.4511(2) 0.1386(2) 0.3871(2) 0.0192(4) Uani 1 1 d .
H13A H 0.5450 0.0792 0.3750 0.023 Uiso 1 1 calc R
C14 C 0.3471(2) 0.1273(2) 0.32208(19) 0.0172(4) Uani 1 1 d .
C15 C 0.2105(2) 0.2140(2) 0.33701(19) 0.0174(4) Uani 1 1 d .
H15A H 0.1404 0.2044 0.2923 0.021 Uiso 1 1 calc R
C16 C 0.1770(2) 0.3153(2) 0.41835(19) 0.0157(4) Uani 1 1 d .
H16A H 0.0839 0.3767 0.4277 0.019 Uiso 1 1 calc R
C21 C 0.2159(2) 0.4020(2) 0.70467(19) 0.0155(4) Uani 1 1 d .
C22 C 0.1773(2) 0.5109(2) 0.78308(19) 0.0159(4) Uani 1 1 d .
C23 C 0.1642(2) 0.4688(2) 0.9130(2) 0.0180(4) Uani 1 1 d .
H23A H 0.1389 0.5402 0.9668 0.022 Uiso 1 1 calc R
C24 C 0.1875(2) 0.3263(2) 0.9634(2) 0.0214(5) Uani 1 1 d .
H24A H 0.1801 0.3006 1.0510 0.026 Uiso 1 1 calc R
C25 C 0.2220(2) 0.2188(2) 0.8862(2) 0.0212(5) Uani 1 1 d .
H25A H 0.2363 0.1206 0.9213 0.025 Uiso 1 1 calc R
C26 C 0.2349(2) 0.2570(2) 0.7590(2) 0.0187(4) Uani 1 1 d .
H26A H 0.2569 0.1841 0.7069 0.022 Uiso 1 1 calc R
C31 C 0.2646(2) 0.6189(2) 0.37983(19) 0.0140(4) Uani 1 1 d .
C32 C 0.4081(2) 0.5848(2) 0.3216(2) 0.0159(4) Uani 1 1 d .
H32A H 0.4804 0.5402 0.3707 0.019 Uiso 1 1 calc R
C33 C 0.4480(2) 0.6144(2) 0.19376(19) 0.0169(4) Uani 1 1 d .
H33A H 0.5464 0.5908 0.1550 0.020 Uiso 1 1 calc R
C34 C 0.3412(2) 0.6792(2) 0.12365(19) 0.0168(4) Uani 1 1 d .
C35 C 0.1970(2) 0.7129(2) 0.1780(2) 0.0181(4) Uani 1 1 d .
H35A H 0.1251 0.7561 0.1282 0.022 Uiso 1 1 calc R
C36 C 0.1590(2) 0.6828(2) 0.3062(2) 0.0167(4) Uani 1 1 d .
H36A H 0.0604 0.7058 0.3444 0.020 Uiso 1 1 calc R
C41 C 0.1852(2) 0.6959(2) 0.59598(19) 0.0146(4) Uani 1 1 d .
C42 C 0.1565(2) 0.6607(2) 0.72783(19) 0.0152(4) Uani 1 1 d .
C43 C 0.1094(2) 0.7743(2) 0.8006(2) 0.0185(4) Uani 1 1 d .
H43A H 0.0871 0.7527 0.8886 0.022 Uiso 1 1 calc R
C44 C 0.0950(2) 0.9151(2) 0.7468(2) 0.0199(4) Uani 1 1 d .
H44A H 0.0623 0.9895 0.7976 0.024 Uiso 1 1 calc R
C45 C 0.1284(2) 0.9493(2) 0.6173(2) 0.0194(4) Uani 1 1 d .
H45A H 0.1209 1.0466 0.5806 0.023 Uiso 1 1 calc R
C46 C 0.1721(2) 0.8415(2) 0.5434(2) 0.0173(4) Uani 1 1 d .
H46A H 0.1938 0.8655 0.4555 0.021 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02624(16) 0.01928(14) 0.02548(15) -0.01024(9) 0.00099(10) -0.00590(9)
Br2 0.02299(15) 0.03517(16) 0.01452(13) -0.00130(9) -0.00235(9) -0.01052(10)
C1 0.0084(10) 0.0186(10) 0.0178(10) -0.0035(8) -0.0028(8) -0.0030(7)
C2 0.0078(10) 0.0190(10) 0.0175(10) -0.0022(8) -0.0032(8) -0.0030(7)
C11 0.0143(11) 0.0154(10) 0.0154(10) 0.0004(8) -0.0013(8) -0.0060(8)
C12 0.0145(11) 0.0200(11) 0.0231(11) -0.0024(8) -0.0063(8) -0.0033(8)
C13 0.0136(11) 0.0173(10) 0.0251(11) -0.0032(8) -0.0029(8) 0.0000(8)
C14 0.0199(12) 0.0152(10) 0.0166(10) -0.0041(8) 0.0011(8) -0.0064(8)
C15 0.0182(11) 0.0179(10) 0.0177(10) -0.0010(8) -0.0047(8) -0.0068(8)
C16 0.0122(11) 0.0154(10) 0.0185(10) -0.0001(8) -0.0023(8) -0.0031(7)
C21 0.0085(10) 0.0198(10) 0.0180(10) -0.0011(8) -0.0025(8) -0.0034(7)
C22 0.0078(10) 0.0219(10) 0.0181(10) -0.0023(8) -0.0012(7) -0.0044(8)
C23 0.0103(11) 0.0244(11) 0.0181(10) -0.0041(8) -0.0002(8) -0.0026(8)
C24 0.0152(11) 0.0296(12) 0.0166(10) 0.0013(9) 0.0006(8) -0.0058(9)
C25 0.0152(11) 0.0218(11) 0.0235(11) 0.0040(9) -0.0014(8) -0.0050(8)
C26 0.0135(11) 0.0190(10) 0.0231(11) -0.0015(8) -0.0027(8) -0.0041(8)
C31 0.0133(11) 0.0122(9) 0.0174(10) -0.0038(7) -0.0023(8) -0.0035(7)
C32 0.0138(11) 0.0153(10) 0.0202(10) -0.0029(8) -0.0055(8) -0.0036(7)
C33 0.0127(11) 0.0198(10) 0.0186(10) -0.0053(8) 0.0004(8) -0.0048(8)
C34 0.0206(12) 0.0176(10) 0.0135(10) -0.0035(8) -0.0016(8) -0.0071(8)
C35 0.0166(11) 0.0191(10) 0.0199(10) -0.0023(8) -0.0073(8) -0.0028(8)
C36 0.0118(11) 0.0179(10) 0.0204(10) -0.0048(8) -0.0026(8) -0.0019(8)
C41 0.0078(10) 0.0182(10) 0.0188(10) -0.0038(8) -0.0029(8) -0.0031(7)
C42 0.0081(10) 0.0199(10) 0.0184(10) -0.0029(8) -0.0036(8) -0.0031(7)
C43 0.0117(11) 0.0266(11) 0.0182(10) -0.0055(8) -0.0030(8) -0.0039(8)
C44 0.0166(11) 0.0209(11) 0.0246(11) -0.0096(9) -0.0049(9) -0.0023(8)
C45 0.0172(12) 0.0180(10) 0.0244(11) -0.0045(8) -0.0054(8) -0.0035(8)
C46 0.0139(11) 0.0184(10) 0.0203(10) -0.0020(8) -0.0042(8) -0.0044(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C21 120.82(19)
C2 C1 C11 119.08(18)
C21 C1 C11 120.10(18)
C1 C2 C41 120.90(19)
C1 C2 C31 119.60(18)
C41 C2 C31 119.45(17)
C16 C11 C12 118.67(19)
C16 C11 C1 119.34(19)
C12 C11 C1 121.93(19)
C13 C12 C11 120.9(2)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C14 C13 C12 118.9(2)
C14 C13 H13A 120.5
C12 C13 H13A 120.5
C15 C14 C13 121.52(19)
C15 C14 Br1 118.97(16)
C13 C14 Br1 119.48(16)
C14 C15 C16 119.11(19)
C14 C15 H15A 120.4
C16 C15 H15A 120.4
C15 C16 C11 120.9(2)
C15 C16 H16A 119.6
C11 C16 H16A 119.6
C26 C21 C22 119.21(19)
C26 C21 C1 121.21(19)
C22 C21 C1 119.55(18)
C23 C22 C21 118.23(19)
C23 C22 C42 122.19(19)
C21 C22 C42 119.57(19)
C24 C23 C22 121.3(2)
C24 C23 H23A 119.3
C22 C23 H23A 119.3
C23 C24 C25 120.5(2)
C23 C24 H24A 119.8
C25 C24 H24A 119.8
C26 C25 C24 119.4(2)
C26 C25 H25A 120.3
C24 C25 H25A 120.3
C25 C26 C21 121.4(2)
C25 C26 H26A 119.3
C21 C26 H26A 119.3
C32 C31 C36 118.64(19)
C32 C31 C2 119.05(18)
C36 C31 C2 122.28(19)
C33 C32 C31 121.45(19)
C33 C32 H32A 119.3
C31 C32 H32A 119.3
C34 C33 C32 118.5(2)
C34 C33 H33A 120.7
C32 C33 H33A 120.7
C33 C34 C35 121.74(19)
C33 C34 Br2 117.81(16)
C35 C34 Br2 120.44(16)
C34 C35 C36 118.97(19)
C34 C35 H35A 120.5
C36 C35 H35A 120.5
C35 C36 C31 120.7(2)
C35 C36 H36A 119.7
C31 C36 H36A 119.7
C46 C41 C42 119.06(19)
C46 C41 C2 121.37(19)
C42 C41 C2 119.57(18)
C43 C42 C41 118.16(19)
C43 C42 C22 122.38(19)
C41 C42 C22 119.46(19)
C44 C43 C42 121.5(2)
C44 C43 H43A 119.3
C42 C43 H43A 119.3
C43 C44 C45 120.3(2)
C43 C44 H44A 119.9
C45 C44 H44A 119.9
C46 C45 C44 119.8(2)
C46 C45 H45A 120.1
C44 C45 H45A 120.1
C45 C46 C41 121.1(2)
C45 C46 H46A 119.4
C41 C46 H46A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.901(2)
Br2 C34 1.903(2)
C1 C2 1.367(3)
C1 C21 1.454(3)
C1 C11 1.495(3)
C2 C41 1.451(3)
C2 C31 1.499(3)
C11 C16 1.398(3)
C11 C12 1.400(3)
C12 C13 1.389(3)
C12 H12A 0.9500
C13 C14 1.389(3)
C13 H13A 0.9500
C14 C15 1.382(3)
C15 C16 1.390(3)
C15 H15A 0.9500
C16 H16A 0.9500
C21 C26 1.411(3)
C21 C22 1.421(3)
C22 C23 1.412(3)
C22 C42 1.455(3)
C23 C24 1.378(3)
C23 H23A 0.9500
C24 C25 1.402(3)
C24 H24A 0.9500
C25 C26 1.379(3)
C25 H25A 0.9500
C26 H26A 0.9500
C31 C32 1.391(3)
C31 C36 1.400(3)
C32 C33 1.385(3)
C32 H32A 0.9500
C33 C34 1.385(3)
C33 H33A 0.9500
C34 C35 1.384(3)
C35 C36 1.387(3)
C35 H35A 0.9500
C36 H36A 0.9500
C41 C46 1.413(3)
C41 C42 1.423(3)
C42 C43 1.414(3)
C43 C44 1.375(3)
C43 H43A 0.9500
C44 C45 1.399(3)
C44 H44A 0.9500
C45 C46 1.378(3)
C45 H45A 0.9500
C46 H46A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C21 C1 C2 C41 -2.1(3)
C11 C1 C2 C41 177.65(18)
C21 C1 C2 C31 175.14(18)
C11 C1 C2 C31 -5.1(3)
C2 C1 C11 C16 -70.4(3)
C21 C1 C11 C16 109.4(2)
C2 C1 C11 C12 106.6(2)
C21 C1 C11 C12 -73.6(3)
C16 C11 C12 C13 0.4(3)
C1 C11 C12 C13 -176.66(19)
C11 C12 C13 C14 -1.3(3)
C12 C13 C14 C15 0.9(3)
C12 C13 C14 Br1 -177.32(16)
C13 C14 C15 C16 0.4(3)
Br1 C14 C15 C16 178.65(15)
C14 C15 C16 C11 -1.4(3)
C12 C11 C16 C15 1.0(3)
C1 C11 C16 C15 178.09(18)
C2 C1 C21 C26 -177.11(19)
C11 C1 C21 C26 3.1(3)
C2 C1 C21 C22 0.8(3)
C11 C1 C21 C22 -178.99(18)
C26 C21 C22 C23 2.2(3)
C1 C21 C22 C23 -175.76(18)
C26 C21 C22 C42 -179.55(18)
C1 C21 C22 C42 2.5(3)
C21 C22 C23 C24 -0.3(3)
C42 C22 C23 C24 -178.52(19)
C22 C23 C24 C25 -1.4(3)
C23 C24 C25 C26 1.1(3)
C24 C25 C26 C21 0.8(3)
C22 C21 C26 C25 -2.5(3)
C1 C21 C26 C25 175.40(19)
C1 C2 C31 C32 -68.9(3)
C41 C2 C31 C32 108.4(2)
C1 C2 C31 C36 109.1(2)
C41 C2 C31 C36 -73.6(3)
C36 C31 C32 C33 0.9(3)
C2 C31 C32 C33 178.99(18)
C31 C32 C33 C34 -0.1(3)
C32 C33 C34 C35 -0.8(3)
C32 C33 C34 Br2 177.67(15)
C33 C34 C35 C36 1.0(3)
Br2 C34 C35 C36 -177.49(15)
C34 C35 C36 C31 -0.2(3)
C32 C31 C36 C35 -0.7(3)
C2 C31 C36 C35 -178.78(19)
C1 C2 C41 C46 179.99(18)
C31 C2 C41 C46 2.7(3)
C1 C2 C41 C42 0.1(3)
C31 C2 C41 C42 -177.15(18)
C46 C41 C42 C43 2.8(3)
C2 C41 C42 C43 -177.28(18)
C46 C41 C42 C22 -176.70(18)
C2 C41 C42 C22 3.2(3)
C23 C22 C42 C43 -5.8(3)
C21 C22 C42 C43 176.01(19)
C23 C22 C42 C41 173.74(19)
C21 C22 C42 C41 -4.5(3)
C41 C42 C43 C44 -1.7(3)
C22 C42 C43 C44 177.80(19)
C42 C43 C44 C45 -0.6(3)
C43 C44 C45 C46 1.7(3)
C44 C45 C46 C41 -0.5(3)
C42 C41 C46 C45 -1.8(3)
C2 C41 C46 C45 178.4(2)
|
1502015.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502015.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502015
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C26 H14 Br4'
_chemical_formula_sum 'C26 H14 Br4'
_chemical_formula_weight 646.01
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 97.5244(14)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 20.7871(3)
_cell_length_b 9.92103(17)
_cell_length_c 22.1583(3)
_cell_measurement_reflns_used 17578
_cell_measurement_temperature 100
_cell_measurement_theta_max 32.7677
_cell_measurement_theta_min 3.488
_cell_volume 4530.35(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 100
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
1 omega -59.00 54.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- 19.9198 -77.0000 -90.0000 113
2 omega -7.00 49.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- 19.9198 -77.0000 90.0000 56
3 omega 15.00 54.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- -20.0760 37.0000 150.0000 39
4 omega -54.00 -26.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- -20.0760 102.0000 -3.0000 28
5 omega -6.00 96.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- 19.9198 37.0000 -90.0000 102
6 omega -6.00 96.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- 19.9198 37.0000 -180.0000 102
7 omega -14.00 99.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- 19.9198 77.0000 0.0000 113
8 omega -64.00 -12.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- -20.0760 102.0000 -3.0000 52
9 omega -64.00 -4.00 1.0000 54.6900
omega____ theta____ kappa____ phi______ frames
- -20.0760 102.0000 176.0000 60
;
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0286044
_diffrn_orient_matrix_UB_12 -0.0395887
_diffrn_orient_matrix_UB_13 0.0052826
_diffrn_orient_matrix_UB_21 -0.0170877
_diffrn_orient_matrix_UB_22 -0.0560324
_diffrn_orient_matrix_UB_23 -0.0140679
_diffrn_orient_matrix_UB_31 0.0085997
_diffrn_orient_matrix_UB_32 0.0202399
_diffrn_orient_matrix_UB_33 -0.0285693
_diffrn_radiation_monochromator mirror
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.7107
_diffrn_reflns_av_R_equivalents 0.0854
_diffrn_reflns_av_sigmaI/netI 0.0704
_diffrn_reflns_limit_h_max 31
_diffrn_reflns_limit_h_min -31
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 33
_diffrn_reflns_limit_l_min -33
_diffrn_reflns_number 42334
_diffrn_reflns_theta_full 30.00
_diffrn_reflns_theta_max 32.84
_diffrn_reflns_theta_min 3.50
_exptl_absorpt_coefficient_mu 7.118
_exptl_absorpt_correction_T_max 0.908
_exptl_absorpt_correction_T_min 0.417
_exptl_absorpt_correction_type gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.894
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 2480
_exptl_crystal_size_max 0.3544
_exptl_crystal_size_mid 0.1255
_exptl_crystal_size_min 0.0254
_refine_diff_density_max 1.127
_refine_diff_density_min -0.825
_refine_diff_density_rms 0.182
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.076
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 271
_refine_ls_number_reflns 7976
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.076
_refine_ls_R_factor_all 0.1101
_refine_ls_R_factor_gt 0.0544
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+33.3882P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0886
_refine_ls_wR_factor_ref 0.1034
_reflns_number_gt 5180
_reflns_number_total 7976
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_005.cif
_cod_data_source_block RAJ19E
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 4530.34(12)
_cod_database_code 1502015
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.64373(2) 0.37548(6) -0.28686(2) 0.03435(12) Uani 1 1 d .
Br2 Br 1.011602(19) 0.63318(4) -0.12488(2) 0.02479(10) Uani 1 1 d .
Br3 Br 0.473876(18) 0.33031(4) 0.10478(2) 0.02209(10) Uani 1 1 d .
Br4 Br 0.90978(2) 0.70036(5) 0.261631(19) 0.02728(11) Uani 1 1 d .
C1 C 0.75861(17) 0.4961(4) -0.02331(16) 0.0119(7) Uani 1 1 d .
C2 C 0.73737(16) 0.4991(4) 0.03165(17) 0.0118(7) Uani 1 1 d .
C11 C 0.72117(17) 0.4593(4) -0.08284(16) 0.0119(7) Uani 1 1 d .
C12 C 0.65676(18) 0.4180(4) -0.09918(17) 0.0146(7) Uani 1 1 d .
H12 H 0.6287 0.4065 -0.0690 0.018 Uiso 1 1 calc R
C13 C 0.63459(18) 0.3940(4) -0.16021(19) 0.0183(8) Uani 1 1 d .
H13 H 0.5909 0.3667 -0.1719 0.022 Uiso 1 1 calc R
C14 C 0.6756(2) 0.4095(4) -0.20407(18) 0.0206(8) Uani 1 1 d .
C15 C 0.73957(19) 0.4511(4) -0.18957(18) 0.0184(8) Uani 1 1 d .
H15 H 0.7674 0.4615 -0.2200 0.022 Uiso 1 1 calc R
C16 C 0.76121(17) 0.4769(4) -0.12869(17) 0.0143(7) Uani 1 1 d .
C21 C 0.82474(17) 0.5344(3) -0.03751(17) 0.0120(7) Uani 1 1 d .
C22 C 0.88123(17) 0.5714(4) -0.00086(18) 0.0151(7) Uani 1 1 d .
H22 H 0.8822 0.5758 0.0421 0.018 Uiso 1 1 calc R
C23 C 0.93638(18) 0.6019(4) -0.02756(19) 0.0168(8) Uani 1 1 d .
H23 H 0.9751 0.6280 -0.0027 0.020 Uiso 1 1 calc R
C24 C 0.93513(17) 0.5947(4) -0.09026(19) 0.0156(7) Uani 1 1 d .
C25 C 0.87920(18) 0.5574(4) -0.12796(18) 0.0157(7) Uani 1 1 d .
H25 H 0.8785 0.5537 -0.1709 0.019 Uiso 1 1 calc R
C26 C 0.82475(17) 0.5258(4) -0.10124(17) 0.0130(7) Uani 1 1 d .
C31 C 0.67108(17) 0.4574(4) 0.04326(16) 0.0118(7) Uani 1 1 d .
C32 C 0.65613(18) 0.3223(4) 0.0491(2) 0.0213(8) Uani 1 1 d .
H32 H 0.6867 0.2554 0.0415 0.026 Uiso 1 1 calc R
C33 C 0.59656(18) 0.2839(4) 0.0661(2) 0.0211(8) Uani 1 1 d .
H33 H 0.5863 0.1913 0.0701 0.025 Uiso 1 1 calc R
C34 C 0.55272(16) 0.3824(4) 0.07682(17) 0.0137(7) Uani 1 1 d .
C35 C 0.56568(18) 0.5175(4) 0.06904(19) 0.0194(8) Uani 1 1 d .
H35 H 0.5341 0.5840 0.0747 0.023 Uiso 1 1 calc R
C36 C 0.62555(17) 0.5544(4) 0.05290(18) 0.0165(7) Uani 1 1 d .
H36 H 0.6354 0.6470 0.0484 0.020 Uiso 1 1 calc R
C41 C 0.77896(17) 0.5470(4) 0.08778(17) 0.0127(7) Uani 1 1 d .
C42 C 0.80574(18) 0.4551(4) 0.13133(17) 0.0168(8) Uani 1 1 d .
H42 H 0.7970 0.3616 0.1256 0.020 Uiso 1 1 calc R
C43 C 0.84543(19) 0.4991(4) 0.18346(18) 0.0184(8) Uani 1 1 d .
H43 H 0.8646 0.4360 0.2127 0.022 Uiso 1 1 calc R
C44 C 0.85631(17) 0.6360(4) 0.19183(17) 0.0168(7) Uani 1 1 d .
C45 C 0.82839(18) 0.7290(4) 0.14964(18) 0.0166(8) Uani 1 1 d .
H45 H 0.8355 0.8228 0.1562 0.020 Uiso 1 1 calc R
C46 C 0.79003(18) 0.6840(4) 0.09788(17) 0.0157(7) Uani 1 1 d .
H46 H 0.7710 0.7475 0.0688 0.019 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0363(2) 0.0478(3) 0.0178(2) -0.0113(2) -0.00096(18) -0.0110(2)
Br2 0.01595(17) 0.0268(2) 0.0340(2) 0.00398(18) 0.01254(16) -0.00157(16)
Br3 0.01309(16) 0.0283(2) 0.0261(2) 0.00162(17) 0.00705(15) -0.00247(15)
Br4 0.0307(2) 0.0306(2) 0.0184(2) 0.00176(18) -0.00477(17) -0.01192(18)
C1 0.0122(15) 0.0092(16) 0.0142(16) 0.0011(13) 0.0012(13) 0.0019(13)
C2 0.0116(15) 0.0066(15) 0.0173(17) 0.0011(13) 0.0025(14) 0.0014(12)
C11 0.0146(16) 0.0098(16) 0.0117(16) -0.0005(13) 0.0035(13) 0.0020(13)
C12 0.0156(16) 0.0124(17) 0.0160(18) -0.0002(14) 0.0024(14) -0.0008(13)
C13 0.0151(17) 0.0161(19) 0.023(2) -0.0021(15) -0.0015(15) -0.0023(14)
C14 0.024(2) 0.021(2) 0.0164(19) -0.0034(16) -0.0002(16) -0.0018(16)
C15 0.0199(18) 0.020(2) 0.0162(18) -0.0036(16) 0.0068(15) 0.0010(15)
C16 0.0146(16) 0.0108(17) 0.0181(18) -0.0025(14) 0.0044(14) 0.0003(13)
C21 0.0127(15) 0.0067(16) 0.0173(17) 0.0015(13) 0.0047(14) 0.0015(12)
C22 0.0150(16) 0.0126(18) 0.0177(18) 0.0015(14) 0.0024(14) 0.0018(14)
C23 0.0119(16) 0.0119(17) 0.027(2) 0.0017(15) 0.0035(15) 0.0020(13)
C24 0.0133(16) 0.0093(16) 0.026(2) 0.0032(15) 0.0078(15) 0.0005(13)
C25 0.0174(17) 0.0140(17) 0.0171(18) 0.0024(15) 0.0073(15) 0.0022(14)
C26 0.0135(16) 0.0106(17) 0.0152(17) 0.0011(14) 0.0027(14) 0.0032(13)
C31 0.0123(15) 0.0136(17) 0.0092(15) 0.0014(13) 0.0010(13) 0.0009(13)
C32 0.0150(17) 0.0135(18) 0.036(2) 0.0039(17) 0.0061(17) 0.0035(14)
C33 0.0160(17) 0.0126(18) 0.036(2) 0.0072(17) 0.0076(17) -0.0016(14)
C34 0.0097(15) 0.0179(18) 0.0138(17) 0.0007(15) 0.0024(13) -0.0007(13)
C35 0.0124(16) 0.0175(19) 0.029(2) -0.0025(17) 0.0053(16) 0.0045(14)
C36 0.0152(16) 0.0102(17) 0.025(2) 0.0006(15) 0.0047(15) 0.0006(13)
C41 0.0119(15) 0.0126(17) 0.0149(17) 0.0005(14) 0.0069(13) -0.0001(13)
C42 0.0220(18) 0.0114(17) 0.0178(18) 0.0000(15) 0.0060(15) 0.0006(14)
C43 0.0217(19) 0.019(2) 0.0142(18) 0.0060(15) 0.0022(15) 0.0005(15)
C44 0.0144(16) 0.0207(19) 0.0159(18) -0.0020(15) 0.0036(14) -0.0035(15)
C45 0.0168(17) 0.0130(18) 0.0205(19) -0.0026(15) 0.0039(15) -0.0012(14)
C46 0.0162(16) 0.0129(18) 0.0175(18) 0.0011(14) 0.0000(14) 0.0007(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 C2 C31 124.6(3)
C1 C2 C41 122.4(3)
C2 C1 C11 127.7(3)
C2 C1 C21 127.0(3)
C11 C1 C21 105.3(3)
C11 C12 H12 120.5
C11 C16 C26 109.2(3)
C12 C11 C1 132.2(3)
C12 C11 C16 119.0(3)
C12 C13 H13 119.7
C13 C12 C11 119.0(3)
C13 C12 H12 120.5
C13 C14 Br1 119.3(3)
C13 C14 C15 122.0(4)
C14 C13 C12 120.5(3)
C14 C13 H13 119.7
C14 C15 H15 121.4
C14 C15 C16 117.3(4)
C15 C14 Br1 118.6(3)
C15 C16 C11 122.1(3)
C15 C16 C26 128.7(3)
C16 C11 C1 108.7(3)
C16 C15 H15 121.4
C21 C22 H22 120.3
C21 C22 C23 119.4(4)
C21 C26 C16 108.5(3)
C22 C21 C1 132.3(3)
C22 C21 C26 119.3(3)
C22 C23 H23 119.8
C23 C22 H22 120.3
C23 C24 Br2 119.2(3)
C23 C24 C25 121.3(3)
C24 C23 C22 120.4(4)
C24 C23 H23 119.8
C24 C25 H25 121.0
C25 C24 Br2 119.4(3)
C25 C26 C16 130.0(3)
C25 C26 C21 121.5(3)
C26 C21 C1 108.3(3)
C26 C25 C24 118.1(4)
C26 C25 H25 121.0
C31 C2 C41 113.0(3)
C31 C32 H32 119.7
C31 C32 C33 120.5(4)
C31 C36 C35 120.7(4)
C31 C36 H36 119.7
C32 C31 C2 120.5(3)
C32 C31 C36 119.4(3)
C32 C33 H33 120.5
C33 C32 H32 119.7
C33 C34 Br3 118.8(3)
C33 C34 C35 121.5(3)
C34 C33 C32 118.9(4)
C34 C33 H33 120.5
C34 C35 H35 120.5
C34 C35 C36 118.9(3)
C35 C34 Br3 119.7(3)
C35 C36 H36 119.7
C36 C31 C2 119.9(3)
C36 C35 H35 120.5
C41 C42 H42 119.7
C41 C42 C43 120.6(4)
C41 C46 H46 119.5
C42 C41 C2 120.3(3)
C42 C41 C46 119.1(3)
C42 C43 H43 120.5
C43 C42 H42 119.7
C43 C44 Br4 120.5(3)
C43 C44 C45 121.1(4)
C44 C43 C42 119.0(4)
C44 C43 H43 120.5
C44 C45 H45 120.3
C45 C44 Br4 118.4(3)
C45 C46 C41 120.9(4)
C45 C46 H46 119.5
C46 C41 C2 120.6(3)
C46 C45 C44 119.3(4)
C46 C45 H45 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.897(4)
Br2 C24 1.892(4)
Br3 C34 1.898(4)
Br4 C44 1.894(4)
C1 C2 1.349(5)
C1 C11 1.487(5)
C1 C21 1.499(5)
C2 C31 1.493(5)
C2 C41 1.496(5)
C11 C12 1.402(5)
C11 C16 1.406(5)
C12 H12 0.9500
C12 C13 1.391(5)
C13 H13 0.9500
C13 C14 1.383(6)
C14 C15 1.389(5)
C15 H15 0.9500
C15 C16 1.389(5)
C16 C26 1.463(5)
C21 C22 1.387(5)
C21 C26 1.415(5)
C22 H22 0.9500
C22 C23 1.391(5)
C23 H23 0.9500
C23 C24 1.388(6)
C24 C25 1.390(5)
C25 H25 0.9500
C25 C26 1.380(5)
C31 C32 1.385(5)
C31 C36 1.386(5)
C32 H32 0.9500
C32 C33 1.393(5)
C33 H33 0.9500
C33 C34 1.378(5)
C34 C35 1.382(5)
C35 H35 0.9500
C35 C36 1.388(5)
C36 H36 0.9500
C41 C42 1.390(5)
C41 C46 1.392(5)
C42 H42 0.9500
C42 C43 1.399(5)
C43 H43 0.9500
C43 C44 1.385(6)
C44 C45 1.386(5)
C45 H45 0.9500
C45 C46 1.382(5)
C46 H46 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
Br1 C14 C15 C16 179.2(3)
Br2 C24 C25 C26 178.0(3)
Br3 C34 C35 C36 175.3(3)
Br4 C44 C45 C46 179.0(3)
C1 C2 C31 C32 80.1(5)
C1 C2 C31 C36 -104.8(5)
C1 C2 C41 C42 -105.4(4)
C1 C2 C41 C46 76.2(5)
C1 C11 C12 C13 178.1(4)
C1 C11 C16 C15 -179.7(3)
C1 C11 C16 C26 -0.4(4)
C1 C21 C22 C23 180.0(4)
C1 C21 C26 C16 -2.6(4)
C1 C21 C26 C25 179.1(3)
C2 C1 C11 C12 -0.7(7)
C2 C1 C11 C16 176.8(4)
C2 C1 C21 C22 5.5(7)
C2 C1 C21 C26 -175.7(4)
C2 C31 C32 C33 173.4(4)
C2 C31 C36 C35 -174.3(4)
C2 C41 C42 C43 179.1(3)
C2 C41 C46 C45 180.0(3)
C11 C1 C2 C31 3.6(6)
C11 C1 C2 C41 -175.8(3)
C11 C1 C21 C22 -176.5(4)
C11 C1 C21 C26 2.3(4)
C11 C12 C13 C14 0.6(6)
C11 C16 C26 C21 1.9(4)
C11 C16 C26 C25 -179.9(4)
C12 C11 C16 C15 -1.8(6)
C12 C11 C16 C26 177.4(3)
C12 C13 C14 Br1 179.8(3)
C12 C13 C14 C15 -1.0(6)
C13 C14 C15 C16 0.0(6)
C14 C15 C16 C11 1.4(6)
C14 C15 C16 C26 -177.7(4)
C15 C16 C26 C21 -178.9(4)
C15 C16 C26 C25 -0.7(7)
C16 C11 C12 C13 0.8(5)
C21 C1 C2 C31 -178.9(3)
C21 C1 C2 C41 1.7(6)
C21 C1 C11 C12 -178.6(4)
C21 C1 C11 C16 -1.1(4)
C21 C22 C23 C24 -0.4(6)
C22 C21 C26 C16 176.4(3)
C22 C21 C26 C25 -2.0(5)
C22 C23 C24 Br2 -178.6(3)
C22 C23 C24 C25 0.2(6)
C23 C24 C25 C26 -0.8(6)
C24 C25 C26 C16 -176.3(4)
C24 C25 C26 C21 1.7(5)
C26 C21 C22 C23 1.3(5)
C31 C2 C41 C42 75.1(4)
C31 C2 C41 C46 -103.2(4)
C31 C32 C33 C34 0.1(6)
C32 C31 C36 C35 0.8(6)
C32 C33 C34 Br3 -176.1(3)
C32 C33 C34 C35 2.3(6)
C33 C34 C35 C36 -3.2(6)
C34 C35 C36 C31 1.6(6)
C36 C31 C32 C33 -1.6(6)
C41 C2 C31 C32 -100.4(4)
C41 C2 C31 C36 74.6(4)
C41 C42 C43 C44 1.7(6)
C42 C41 C46 C45 1.6(6)
C42 C43 C44 Br4 -179.9(3)
C42 C43 C44 C45 0.2(6)
C43 C44 C45 C46 -1.2(6)
C44 C45 C46 C41 0.2(6)
C46 C41 C42 C43 -2.6(6)
|
1502016.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502016.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502016
loop_
_publ_author_name
'Navale, Tushar S.'
'Thakur, Khushabu'
'Rathore, Rajendra'
_publ_section_title
;
Sequential oxidative transformation of tetraarylethylenes to
9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
oxidant.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1634
_journal_page_last 1637
_journal_paper_doi 10.1021/ol200069c
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C30 H26'
_chemical_formula_sum 'C30 H26'
_chemical_formula_weight 386.51
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_Hall '-C 2yc'
_space_group_name_H-M_alt 'C 1 2/c 1'
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 97.210(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 20.3854(4)
_cell_length_b 10.05033(19)
_cell_length_c 21.6071(5)
_cell_measurement_reflns_used 6615
_cell_measurement_temperature 100
_cell_measurement_theta_max 70.5956
_cell_measurement_theta_min 4.1212
_cell_volume 4391.86(16)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 100.0
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
1 omega -98.00 -19.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 131.0000 148.0000 79
2 omega 31.00 62.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -131.0000 78.0000 31
3 omega 90.00 124.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -131.0000 78.0000 34
4 omega 35.00 70.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -28.0000 79.0000 35
5 omega 72.00 174.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 28.0000 100.0000 102
6 omega -40.00 22.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 37.0000 30.0000 62
7 omega -115.00 -90.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 -131.0000 -101.0000 25
8 omega -117.00 -45.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 -37.0000 -90.0000 72
9 omega 36.00 133.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -77.0000 30.0000 97
10 omega 95.00 170.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 125.0000 90.0000 75
11 omega 95.00 120.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -137.0000 -144.0000 25
12 omega 31.00 68.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -45.0000 60.0000 37
13 omega -119.00 -7.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 -77.0000 30.0000 112
14 omega -117.00 -14.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- -40.7737 -37.0000 90.0000 103
15 omega 7.00 119.00 1.0000 6.2000
omega____ theta____ kappa____ phi______ frames
- 40.7737 77.0000 -150.0000 112
16 omega 39.00 171.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 15.0000 -90.0000 132
17 omega 26.00 77.00 1.0000 56.4400
omega____ theta____ kappa____ phi______ frames
- 100.5756 -45.0000 -180.0000 51
;
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0674451
_diffrn_orient_matrix_UB_12 0.0610743
_diffrn_orient_matrix_UB_13 -0.0251727
_diffrn_orient_matrix_UB_21 0.0297826
_diffrn_orient_matrix_UB_22 0.1405108
_diffrn_orient_matrix_UB_23 0.0094343
_diffrn_orient_matrix_UB_31 0.0192696
_diffrn_orient_matrix_UB_32 -0.0034243
_diffrn_orient_matrix_UB_33 -0.0666499
_diffrn_radiation_monochromator mirror
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.5418
_diffrn_reflns_av_R_equivalents 0.0415
_diffrn_reflns_av_sigmaI/netI 0.0329
_diffrn_reflns_limit_h_max 24
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 14666
_diffrn_reflns_theta_full 70.00
_diffrn_reflns_theta_max 70.73
_diffrn_reflns_theta_min 4.12
_exptl_absorpt_coefficient_mu 0.494
_exptl_absorpt_correction_T_max 1.0
_exptl_absorpt_correction_T_min 0.78711
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.169
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1648
_exptl_crystal_size_max 0.09
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.217
_refine_diff_density_min -0.183
_refine_diff_density_rms 0.042
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.008
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 275
_refine_ls_number_reflns 4130
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.008
_refine_ls_R_factor_all 0.0544
_refine_ls_R_factor_gt 0.0394
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0989
_refine_ls_wR_factor_ref 0.1052
_reflns_number_gt 3177
_reflns_number_total 4130
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200069c_si_006.cif
_cod_data_source_block RAJ19L
_cod_original_cell_volume 4391.87(17)
_cod_database_code 1502016
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.25720(6) 0.49587(11) 0.47640(6) 0.0196(3) Uani 1 1 d .
C2 C 0.23658(6) 0.49693(11) 0.53349(6) 0.0194(3) Uani 1 1 d .
C11 C 0.32366(6) 0.53585(11) 0.46070(6) 0.0198(3) Uani 1 1 d .
C12 C 0.38208(6) 0.57384(12) 0.49723(7) 0.0217(3) Uani 1 1 d .
H12 H 0.3842 0.5779 0.5414 0.026 Uiso 1 1 calc R
C13 C 0.43732(6) 0.60578(12) 0.46806(7) 0.0236(3) Uani 1 1 d .
H13 H 0.4770 0.6313 0.4931 0.028 Uiso 1 1 calc R
C14 C 0.43638(6) 0.60155(12) 0.40348(7) 0.0236(3) Uani 1 1 d .
C15 C 0.37805(7) 0.56300(12) 0.36720(7) 0.0236(3) Uani 1 1 d .
H15 H 0.3760 0.5601 0.3231 0.028 Uiso 1 1 calc R
C16 C 0.32304(6) 0.52897(11) 0.39555(6) 0.0210(3) Uani 1 1 d .
C17 C 0.49733(7) 0.63511(14) 0.37372(8) 0.0318(3) Uani 1 1 d .
H17A H 0.5157 0.5536 0.3579 0.048 Uiso 1 1 calc R
H17C H 0.5303 0.6765 0.4048 0.048 Uiso 1 1 calc R
H17B H 0.4856 0.6971 0.3391 0.048 Uiso 1 1 calc R
C21 C 0.21846(6) 0.46053(11) 0.41574(6) 0.0196(3) Uani 1 1 d .
C22 C 0.15341(6) 0.41742(12) 0.39967(7) 0.0220(3) Uani 1 1 d .
H22 H 0.1254 0.4031 0.4310 0.026 Uiso 1 1 calc R
C23 C 0.13015(7) 0.39565(13) 0.33710(7) 0.0254(3) Uani 1 1 d .
H23 H 0.0858 0.3670 0.3264 0.031 Uiso 1 1 calc R
C24 C 0.16968(7) 0.41440(13) 0.28951(7) 0.0268(3) Uani 1 1 d .
C25 C 0.23472(7) 0.45705(13) 0.30573(7) 0.0251(3) Uani 1 1 d .
H25 H 0.2628 0.4700 0.2743 0.030 Uiso 1 1 calc R
C26 C 0.25818(6) 0.48043(11) 0.36778(6) 0.0210(3) Uani 1 1 d .
C27 C 0.14333(8) 0.39227(17) 0.22204(8) 0.0393(4) Uani 1 1 d .
H27A H 0.0992 0.3525 0.2193 0.059 Uiso 1 1 calc R
H27B H 0.1730 0.3323 0.2030 0.059 Uiso 1 1 calc R
H27C H 0.1407 0.4776 0.2000 0.059 Uiso 1 1 calc R
C31 C 0.27960(6) 0.54420(12) 0.59019(6) 0.0200(3) Uani 1 1 d .
C32 C 0.28860(7) 0.68001(12) 0.60162(7) 0.0239(3) Uani 1 1 d .
H32 H 0.2665 0.7429 0.5735 0.029 Uiso 1 1 calc R
C33 C 0.32959(7) 0.72390(13) 0.65372(7) 0.0250(3) Uani 1 1 d .
H33 H 0.3349 0.8167 0.6610 0.030 Uiso 1 1 calc R
C34 C 0.36301(6) 0.63431(13) 0.69557(6) 0.0231(3) Uani 1 1 d .
C35 C 0.35354(7) 0.49885(13) 0.68391(6) 0.0245(3) Uani 1 1 d .
H35 H 0.3760 0.4359 0.7117 0.029 Uiso 1 1 calc R
C36 C 0.31176(7) 0.45413(12) 0.63227(6) 0.0230(3) Uani 1 1 d .
H36 H 0.3052 0.3613 0.6258 0.028 Uiso 1 1 calc R
C37 C 0.40617(8) 0.68493(15) 0.75237(7) 0.0329(3) Uani 1 1 d .
H37C H 0.3790 0.7015 0.7859 0.049 Uiso 1 1 calc R
H37B H 0.4276 0.7679 0.7420 0.049 Uiso 1 1 calc R
H37A H 0.4400 0.6183 0.7661 0.049 Uiso 1 1 calc R
C41 C 0.16948(6) 0.45308(12) 0.54595(6) 0.0193(3) Uani 1 1 d .
C42 C 0.15503(7) 0.31909(13) 0.55264(7) 0.0261(3) Uani 1 1 d .
H42 H 0.1870 0.2538 0.5457 0.031 Uiso 1 1 calc R
C43 C 0.09439(7) 0.27958(13) 0.56941(7) 0.0257(3) Uani 1 1 d .
H43 H 0.0857 0.1875 0.5742 0.031 Uiso 1 1 calc R
C44 C 0.04635(6) 0.37212(13) 0.57931(6) 0.0219(3) Uani 1 1 d .
C45 C 0.06050(7) 0.50635(13) 0.57114(7) 0.0255(3) Uani 1 1 d .
H45 H 0.0279 0.5714 0.5765 0.031 Uiso 1 1 calc R
C46 C 0.12123(7) 0.54642(12) 0.55538(7) 0.0236(3) Uani 1 1 d .
H46 H 0.1301 0.6385 0.5510 0.028 Uiso 1 1 calc R
C47 C -0.01854(7) 0.32982(15) 0.59979(7) 0.0297(3) Uani 1 1 d .
H47A H -0.0543 0.3451 0.5658 0.044 Uiso 1 1 calc R
H47C H -0.0269 0.3818 0.6364 0.044 Uiso 1 1 calc R
H47B H -0.0166 0.2350 0.6105 0.044 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0181(6) 0.0161(5) 0.0249(7) 0.0005(5) 0.0031(5) 0.0016(4)
C2 0.0204(6) 0.0151(5) 0.0229(7) 0.0017(5) 0.0040(5) 0.0023(4)
C11 0.0188(6) 0.0160(5) 0.0249(7) 0.0011(5) 0.0044(5) 0.0026(4)
C12 0.0216(6) 0.0189(5) 0.0248(7) 0.0012(5) 0.0035(5) 0.0025(4)
C13 0.0181(6) 0.0202(6) 0.0322(8) 0.0011(5) 0.0025(5) 0.0014(4)
C14 0.0209(6) 0.0179(5) 0.0331(8) 0.0021(5) 0.0074(6) 0.0024(4)
C15 0.0235(7) 0.0227(6) 0.0258(7) 0.0011(5) 0.0079(6) 0.0018(5)
C16 0.0214(6) 0.0175(5) 0.0245(7) 0.0012(5) 0.0048(5) 0.0026(4)
C17 0.0248(7) 0.0346(7) 0.0382(9) 0.0009(6) 0.0120(6) -0.0019(5)
C21 0.0209(6) 0.0156(5) 0.0225(7) 0.0002(5) 0.0035(5) 0.0023(4)
C22 0.0214(6) 0.0200(5) 0.0251(7) 0.0000(5) 0.0054(5) -0.0006(4)
C23 0.0229(6) 0.0238(6) 0.0293(8) -0.0028(5) 0.0024(6) -0.0034(5)
C24 0.0296(7) 0.0251(6) 0.0253(8) -0.0031(5) 0.0019(6) -0.0003(5)
C25 0.0265(7) 0.0272(6) 0.0225(7) -0.0028(5) 0.0070(6) 0.0012(5)
C26 0.0212(6) 0.0187(5) 0.0235(7) -0.0004(5) 0.0049(5) 0.0022(4)
C27 0.0382(9) 0.0514(9) 0.0273(8) -0.0104(7) 0.0009(7) -0.0090(7)
C31 0.0186(6) 0.0212(6) 0.0212(7) -0.0002(5) 0.0069(5) 0.0006(4)
C32 0.0234(7) 0.0212(6) 0.0268(7) 0.0003(5) 0.0020(6) 0.0020(5)
C33 0.0244(7) 0.0215(6) 0.0293(8) -0.0029(5) 0.0045(6) -0.0016(5)
C34 0.0190(6) 0.0298(6) 0.0217(7) 0.0000(5) 0.0071(5) -0.0024(5)
C35 0.0262(7) 0.0279(6) 0.0199(7) 0.0042(5) 0.0055(5) 0.0029(5)
C36 0.0268(7) 0.0211(5) 0.0220(7) 0.0008(5) 0.0063(5) 0.0000(5)
C37 0.0316(8) 0.0380(7) 0.0285(8) -0.0005(6) 0.0021(6) -0.0084(6)
C41 0.0201(6) 0.0205(6) 0.0176(6) 0.0008(5) 0.0029(5) 0.0002(4)
C42 0.0226(7) 0.0203(6) 0.0365(8) 0.0028(5) 0.0079(6) 0.0040(5)
C43 0.0229(7) 0.0206(6) 0.0340(8) 0.0050(5) 0.0049(6) -0.0009(5)
C44 0.0191(6) 0.0285(6) 0.0178(7) 0.0006(5) 0.0015(5) -0.0001(5)
C45 0.0208(6) 0.0246(6) 0.0315(8) -0.0033(6) 0.0048(6) 0.0041(5)
C46 0.0237(7) 0.0198(6) 0.0276(7) -0.0015(5) 0.0039(5) 0.0009(5)
C47 0.0228(7) 0.0355(7) 0.0316(8) 0.0000(6) 0.0068(6) -0.0015(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 C2 C31 122.24(12)
C1 C2 C41 123.98(12)
C2 C1 C11 126.90(12)
C2 C1 C21 127.94(12)
C11 C12 H12 120.4
C11 C16 C26 108.68(11)
C12 C11 C1 132.76(13)
C12 C11 C16 118.59(12)
C12 C13 H13 118.8
C13 C12 C11 119.13(13)
C13 C12 H12 120.4
C13 C14 C15 118.35(12)
C13 C14 C17 120.78(12)
C14 C13 C12 122.33(12)
C14 C13 H13 118.8
C14 C15 H15 120.0
C14 C17 H17A 109.5
C14 C17 H17C 109.5
C14 C17 H17B 109.5
C15 C14 C17 120.85(13)
C15 C16 C11 121.56(12)
C15 C16 C26 129.75(13)
C16 C11 C1 108.64(11)
C16 C15 C14 120.00(13)
C16 C15 H15 120.0
H17A C17 H17C 109.5
H17A C17 H17B 109.5
H17C C17 H17B 109.5
C21 C1 C11 105.12(11)
C21 C22 H22 120.4
C21 C26 C16 108.59(12)
C22 C21 C1 132.55(13)
C22 C21 C26 118.49(13)
C22 C23 H23 118.8
C22 C23 C24 122.40(13)
C23 C22 C21 119.14(13)
C23 C22 H22 120.4
C23 C24 C27 121.61(13)
C24 C23 H23 118.8
C24 C25 H25 120.1
C24 C27 H27A 109.5
C24 C27 H27B 109.5
C24 C27 H27C 109.5
C25 C24 C23 118.33(13)
C25 C24 C27 120.05(14)
C25 C26 C16 129.55(13)
C25 C26 C21 121.85(12)
C26 C21 C1 108.93(11)
C26 C25 C24 119.77(13)
C26 C25 H25 120.1
H27A C27 H27B 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C31 C2 C41 113.78(11)
C31 C32 H32 119.8
C31 C36 C35 120.41(11)
C31 C36 H36 119.8
C32 C31 C2 120.50(11)
C32 C33 H33 119.4
C32 C33 C34 121.16(12)
C33 C32 C31 120.48(12)
C33 C32 H32 119.8
C33 C34 C35 117.97(12)
C33 C34 C37 119.94(12)
C34 C33 H33 119.4
C34 C35 H35 119.4
C34 C37 H37C 109.5
C34 C37 H37B 109.5
C34 C37 H37A 109.5
C35 C34 C37 122.06(12)
C35 C36 H36 119.8
C36 C31 C2 120.72(11)
C36 C31 C32 118.78(12)
C36 C35 C34 121.19(12)
C36 C35 H35 119.4
H37C C37 H37B 109.5
H37C C37 H37A 109.5
H37B C37 H37A 109.5
C41 C42 H42 119.6
C41 C46 H46 119.7
C42 C41 C2 121.03(11)
C42 C41 C46 118.34(12)
C42 C43 H43 119.4
C43 C42 C41 120.75(12)
C43 C42 H42 119.6
C43 C44 C45 117.89(12)
C43 C44 C47 121.26(12)
C44 C43 C42 121.16(12)
C44 C43 H43 119.4
C44 C45 H45 119.4
C44 C47 H47A 109.5
C44 C47 H47C 109.5
C44 C47 H47B 109.5
C45 C44 C47 120.84(12)
C45 C46 C41 120.65(12)
C45 C46 H46 119.7
C46 C41 C2 120.48(11)
C46 C45 C44 121.19(12)
C46 C45 H45 119.4
H47A C47 H47C 109.5
H47A C47 H47B 109.5
H47C C47 H47B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3521(19)
C1 C11 1.4924(18)
C1 C21 1.4859(19)
C2 C31 1.4921(19)
C2 C41 1.4934(17)
C11 C12 1.3969(18)
C11 C16 1.4078(19)
C12 H12 0.9500
C12 C13 1.3952(19)
C13 H13 0.9500
C13 C14 1.394(2)
C14 C15 1.3945(19)
C14 C17 1.5071(19)
C15 H15 0.9500
C15 C16 1.3865(19)
C16 C26 1.4652(18)
C17 H17A 0.9800
C17 H17C 0.9800
C17 H17B 0.9800
C21 C22 1.3969(18)
C21 C26 1.4073(19)
C22 H22 0.9500
C22 C23 1.393(2)
C23 H23 0.9500
C23 C24 1.396(2)
C24 C25 1.396(2)
C24 C27 1.506(2)
C25 H25 0.9500
C25 C26 1.386(2)
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C31 C32 1.3951(17)
C31 C36 1.3878(18)
C32 H32 0.9500
C32 C33 1.387(2)
C33 H33 0.9500
C33 C34 1.3921(19)
C34 C35 1.3937(19)
C34 C37 1.506(2)
C35 H35 0.9500
C35 C36 1.391(2)
C36 H36 0.9500
C37 H37C 0.9800
C37 H37B 0.9800
C37 H37A 0.9800
C41 C42 1.3899(17)
C41 C46 1.3926(17)
C42 H42 0.9500
C42 C43 1.389(2)
C43 H43 0.9500
C43 C44 1.3864(18)
C44 C45 1.3955(18)
C44 C47 1.5077(19)
C45 H45 0.9500
C45 C46 1.384(2)
C46 H46 0.9500
C47 H47A 0.9800
C47 H47C 0.9800
C47 H47B 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 C2 C31 C32 78.07(16)
C1 C2 C31 C36 -101.47(15)
C1 C2 C41 C42 81.38(17)
C1 C2 C41 C46 -103.06(15)
C1 C11 C12 C13 179.83(12)
C1 C11 C16 C15 178.86(11)
C1 C11 C16 C26 -2.07(13)
C1 C21 C22 C23 178.02(12)
C1 C21 C26 C16 -0.13(13)
C1 C21 C26 C25 -179.18(11)
C2 C1 C11 C12 5.3(2)
C2 C1 C11 C16 -175.80(11)
C2 C1 C21 C22 -1.5(2)
C2 C1 C21 C26 176.63(11)
C2 C31 C32 C33 -178.78(12)
C2 C31 C36 C35 177.82(12)
C2 C41 C42 C43 174.54(13)
C2 C41 C46 C45 -175.56(13)
C11 C1 C2 C31 1.78(18)
C11 C1 C2 C41 -178.86(11)
C11 C1 C21 C22 -179.23(12)
C11 C1 C21 C26 -1.09(12)
C11 C12 C13 C14 0.19(18)
C11 C16 C26 C21 1.39(13)
C11 C16 C26 C25 -179.65(12)
C12 C11 C16 C15 -2.11(17)
C12 C11 C16 C26 176.96(10)
C12 C13 C14 C15 -0.46(18)
C12 C13 C14 C17 -179.23(12)
C13 C14 C15 C16 -0.55(17)
C14 C15 C16 C11 1.85(18)
C14 C15 C16 C26 -177.00(12)
C15 C16 C26 C21 -179.64(12)
C15 C16 C26 C25 -0.7(2)
C16 C11 C12 C13 1.07(17)
C17 C14 C15 C16 178.22(12)
C21 C1 C2 C31 -175.47(11)
C21 C1 C2 C41 3.89(19)
C21 C1 C11 C12 -176.90(12)
C21 C1 C11 C16 1.95(12)
C21 C22 C23 C24 0.48(19)
C22 C21 C26 C16 178.32(10)
C22 C21 C26 C25 -0.73(18)
C22 C23 C24 C25 -0.3(2)
C22 C23 C24 C27 -179.09(13)
C23 C24 C25 C26 -0.44(19)
C24 C25 C26 C16 -177.88(12)
C24 C25 C26 C21 0.95(19)
C26 C21 C22 C23 0.02(17)
C27 C24 C25 C26 178.40(13)
C31 C2 C41 C42 -99.21(15)
C31 C2 C41 C46 76.35(15)
C31 C32 C33 C34 0.4(2)
C32 C31 C36 C35 -1.7(2)
C32 C33 C34 C35 -0.6(2)
C32 C33 C34 C37 -178.86(13)
C33 C34 C35 C36 -0.3(2)
C34 C35 C36 C31 1.5(2)
C36 C31 C32 C33 0.8(2)
C37 C34 C35 C36 177.85(13)
C41 C2 C31 C32 -101.35(14)
C41 C2 C31 C36 79.11(15)
C41 C42 C43 C44 0.7(2)
C42 C41 C46 C45 0.1(2)
C42 C43 C44 C45 0.8(2)
C42 C43 C44 C47 -177.74(14)
C43 C44 C45 C46 -1.8(2)
C44 C45 C46 C41 1.4(2)
C46 C41 C42 C43 -1.1(2)
C47 C44 C45 C46 176.74(13)
|
1502017.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502017.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502017
loop_
_publ_author_name
'Witek, Jason A.'
'Weinreb, Steven M.'
_publ_section_title
;
Investigation of the stereochemistry of intermolecular conjugate
additions of nucleophiles to acyclic nitrosoalkenes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1258
_journal_page_last 1260
_journal_paper_doi 10.1021/ol2000793
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C27 H33 N O7 S'
_chemical_formula_sum 'C27 H33 N O7 S'
_chemical_formula_weight 515.60
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 78.441(7)
_cell_angle_beta 69.879(7)
_cell_angle_gamma 73.730(7)
_cell_formula_units_Z 2
_cell_length_a 10.625(2)
_cell_length_b 11.575(2)
_cell_length_c 12.145(2)
_cell_measurement_reflns_used 1513
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 28.262
_cell_measurement_theta_min 2.307
_cell_volume 1337.3(4)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0326
_diffrn_reflns_av_sigmaI/netI 0.0796
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 12607
_diffrn_reflns_theta_full 28.39
_diffrn_reflns_theta_max 28.39
_diffrn_reflns_theta_min 1.80
_exptl_absorpt_coefficient_mu 0.166
_exptl_absorpt_correction_T_max 0.9868
_exptl_absorpt_correction_T_min 0.9550
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.280
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 548
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.343
_refine_diff_density_min -0.274
_refine_diff_density_rms 0.046
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment noref
_refine_ls_matrix_type full
_refine_ls_number_parameters 329
_refine_ls_number_reflns 6229
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.053
_refine_ls_R_factor_all 0.1675
_refine_ls_R_factor_gt 0.0854
_refine_ls_shift/su_max 0.012
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0845P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1741
_refine_ls_wR_factor_ref 0.2084
_reflns_number_gt 3194
_reflns_number_total 6229
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000793_si_001.cif
_cod_data_source_block jaw1s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502017
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4946(4) -0.0604(3) 0.2891(3) 0.0520(9) Uani 1 1 d .
C2 C 0.6225(5) -0.0502(4) 0.2827(4) 0.0763(12) Uani 1 1 d .
H2 H 0.6326 0.0185 0.3045 0.092 Uiso 1 1 calc R
C3 C 0.7358(5) -0.1421(4) 0.2440(4) 0.0821(13) Uani 1 1 d .
H3 H 0.8222 -0.1343 0.2395 0.098 Uiso 1 1 calc R
C4 C 0.7245(5) -0.2446(4) 0.2118(3) 0.0663(11) Uani 1 1 d .
C5 C 0.8497(5) -0.3451(4) 0.1702(5) 0.1038(17) Uani 1 1 d .
H5A H 0.9270 -0.3107 0.1243 0.156 Uiso 1 1 calc R
H5B H 0.8316 -0.3916 0.1225 0.156 Uiso 1 1 calc R
H5C H 0.8702 -0.3967 0.2372 0.156 Uiso 1 1 calc R
C6 C 0.5952(5) -0.2536(4) 0.2210(4) 0.0770(12) Uani 1 1 d .
H6 H 0.5850 -0.3232 0.2011 0.092 Uiso 1 1 calc R
C7 C 0.4803(4) -0.1630(4) 0.2587(4) 0.0670(11) Uani 1 1 d .
H7 H 0.3938 -0.1711 0.2635 0.080 Uiso 1 1 calc R
C8 C 0.2674(4) 0.2178(4) 0.1205(4) 0.0715(12) Uani 1 1 d .
H8A H 0.2099 0.1595 0.1464 0.086 Uiso 1 1 calc R
H8B H 0.2746 0.2485 0.0386 0.086 Uiso 1 1 calc R
C9 C 0.2069(4) 0.3208(3) 0.1971(3) 0.0534(9) Uani 1 1 d .
H9 H 0.1114 0.3204 0.2443 0.064 Uiso 1 1 calc R
C10 C 0.2999(3) 0.2934(3) 0.2772(3) 0.0450(8) Uani 1 1 d .
H10 H 0.2447 0.2893 0.3606 0.054 Uiso 1 1 calc R
C11 C 0.3763(3) 0.3956(3) 0.2447(3) 0.0436(8) Uani 1 1 d .
H11 H 0.4537 0.3756 0.1736 0.052 Uiso 1 1 calc R
C12 C 0.2725(3) 0.5069(3) 0.2039(3) 0.0455(8) Uani 1 1 d .
C13 C 0.2186(3) 0.4471(3) 0.1328(3) 0.0536(9) Uani 1 1 d .
H13A H 0.1293 0.4947 0.1279 0.064 Uiso 1 1 calc R
H13B H 0.2817 0.4411 0.0534 0.064 Uiso 1 1 calc R
C14 C 0.4403(4) 0.4118(3) 0.3362(3) 0.0524(9) Uani 1 1 d .
H14 H 0.4455 0.4970 0.3222 0.063 Uiso 1 1 calc R
C15 C 0.3530(4) 0.3910(4) 0.4654(3) 0.0728(12) Uani 1 1 d .
H15A H 0.3521 0.3067 0.4862 0.109 Uiso 1 1 calc R
H15B H 0.2606 0.4382 0.4753 0.109 Uiso 1 1 calc R
H15C H 0.3917 0.4151 0.5154 0.109 Uiso 1 1 calc R
C16 C 0.5879(4) 0.3383(3) 0.3119(3) 0.0552(9) Uani 1 1 d .
C17 C 0.6293(5) 0.2333(4) 0.3814(4) 0.0743(12) Uani 1 1 d .
H17 H 0.5638 0.2058 0.4473 0.089 Uiso 1 1 calc R
C18 C 0.7639(5) 0.1686(4) 0.3561(5) 0.0839(14) Uani 1 1 d .
H18 H 0.7882 0.0985 0.4043 0.101 Uiso 1 1 calc R
C19 C 0.8616(5) 0.2074(4) 0.2604(5) 0.0886(14) Uani 1 1 d .
H19 H 0.9529 0.1641 0.2432 0.106 Uiso 1 1 calc R
C20 C 0.8249(5) 0.3107(5) 0.1894(5) 0.0988(16) Uani 1 1 d .
H20 H 0.8914 0.3376 0.1240 0.119 Uiso 1 1 calc R
C21 C 0.6902(4) 0.3743(4) 0.2148(4) 0.0784(13) Uani 1 1 d .
H21 H 0.6669 0.4437 0.1654 0.094 Uiso 1 1 calc R
C22 C 0.1572(4) 0.5600(3) 0.3084(3) 0.0584(10) Uani 1 1 d .
C23 C 0.1007(7) 0.6955(5) 0.4539(5) 0.123(2) Uani 1 1 d .
H23A H 0.0353 0.6456 0.4964 0.148 Uiso 1 1 calc R
H23B H 0.1527 0.6974 0.5051 0.148 Uiso 1 1 calc R
C24 C 0.0290(6) 0.8134(6) 0.4264(5) 0.128(2) Uani 1 1 d .
H24A H 0.0931 0.8598 0.3746 0.192 Uiso 1 1 calc R
H24B H -0.0199 0.8509 0.4976 0.192 Uiso 1 1 calc R
H24C H -0.0352 0.8104 0.3881 0.192 Uiso 1 1 calc R
C25 C 0.3407(4) 0.6052(3) 0.1249(3) 0.0505(9) Uani 1 1 d .
C26 C 0.2917(5) 0.8017(4) 0.0225(4) 0.0835(14) Uani 1 1 d .
H26A H 0.3221 0.7900 -0.0603 0.100 Uiso 1 1 calc R
H26B H 0.3683 0.8137 0.0415 0.100 Uiso 1 1 calc R
C27 C 0.1782(7) 0.9061(5) 0.0451(6) 0.145(3) Uani 1 1 d .
H27A H 0.1031 0.8939 0.0253 0.218 Uiso 1 1 calc R
H27B H 0.2070 0.9767 -0.0021 0.218 Uiso 1 1 calc R
H27C H 0.1488 0.9173 0.1271 0.218 Uiso 1 1 calc R
N1 N 0.3967(3) 0.1754(2) 0.2497(2) 0.0475(7) Uani 1 1 d .
O1 O 0.2323(3) 0.0274(2) 0.3308(3) 0.0779(8) Uani 1 1 d .
O2 O 0.3439(3) 0.0802(2) 0.4548(2) 0.0815(9) Uani 1 1 d .
O3 O 0.4022(3) 0.1623(2) 0.1334(2) 0.0588(7) Uani 1 1 d .
O4 O 0.0498(3) 0.5303(3) 0.3519(2) 0.0792(9) Uani 1 1 d .
O5 O 0.1949(3) 0.6412(3) 0.3478(2) 0.0870(9) Uani 1 1 d .
O6 O 0.2468(3) 0.6969(2) 0.0943(2) 0.0714(8) Uani 1 1 d .
O7 O 0.4617(3) 0.6017(2) 0.0913(2) 0.0650(7) Uani 1 1 d .
S1 S 0.35014(10) 0.05463(8) 0.34239(8) 0.0582(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.057(2) 0.046(2) 0.048(2) 0.0012(16) -0.0157(17) -0.0107(18)
C2 0.074(3) 0.064(3) 0.102(3) -0.023(2) -0.037(3) -0.010(2)
C3 0.064(3) 0.083(3) 0.104(4) -0.016(3) -0.042(3) -0.001(3)
C4 0.077(3) 0.056(3) 0.063(3) -0.001(2) -0.032(2) -0.002(2)
C5 0.089(4) 0.091(4) 0.120(4) -0.030(3) -0.046(3) 0.029(3)
C6 0.082(3) 0.058(3) 0.094(3) -0.020(2) -0.028(3) -0.011(2)
C7 0.061(3) 0.059(3) 0.084(3) -0.015(2) -0.021(2) -0.014(2)
C8 0.086(3) 0.063(3) 0.080(3) -0.012(2) -0.050(2) -0.007(2)
C9 0.043(2) 0.058(2) 0.058(2) -0.0013(19) -0.0152(17) -0.0143(17)
C10 0.0451(19) 0.0409(19) 0.0409(18) -0.0028(15) -0.0046(15) -0.0092(16)
C11 0.0419(19) 0.0458(19) 0.0388(18) -0.0033(15) -0.0074(15) -0.0107(16)
C12 0.0414(19) 0.0420(19) 0.0430(19) -0.0007(15) -0.0037(15) -0.0085(15)
C13 0.041(2) 0.060(2) 0.053(2) 0.0002(18) -0.0132(16) -0.0072(17)
C14 0.059(2) 0.050(2) 0.049(2) -0.0036(17) -0.0139(17) -0.0174(18)
C15 0.082(3) 0.087(3) 0.049(2) -0.010(2) -0.014(2) -0.026(2)
C16 0.063(2) 0.057(2) 0.057(2) 0.0018(19) -0.0258(19) -0.026(2)
C17 0.076(3) 0.081(3) 0.074(3) 0.022(2) -0.038(2) -0.034(3)
C18 0.071(3) 0.077(3) 0.114(4) 0.017(3) -0.052(3) -0.024(3)
C19 0.067(3) 0.073(3) 0.131(4) -0.001(3) -0.043(3) -0.016(3)
C20 0.066(3) 0.092(4) 0.114(4) 0.016(3) -0.013(3) -0.020(3)
C21 0.064(3) 0.071(3) 0.084(3) 0.019(2) -0.018(2) -0.013(2)
C22 0.059(3) 0.053(2) 0.045(2) 0.0002(18) -0.0011(19) -0.007(2)
C23 0.155(5) 0.089(4) 0.084(4) -0.040(3) 0.024(3) -0.018(4)
C24 0.101(4) 0.113(5) 0.123(5) -0.044(4) 0.015(3) 0.008(4)
C25 0.056(2) 0.043(2) 0.044(2) -0.0045(16) -0.0065(18) -0.0080(18)
C26 0.090(3) 0.052(3) 0.083(3) 0.021(2) -0.012(3) -0.016(2)
C27 0.152(6) 0.070(4) 0.142(5) 0.018(3) 0.001(4) 0.005(4)
N1 0.0482(17) 0.0455(17) 0.0420(16) -0.0029(13) -0.0064(13) -0.0109(14)
O1 0.0490(16) 0.0667(18) 0.104(2) -0.0075(15) 0.0007(14) -0.0243(14)
O2 0.123(2) 0.0592(17) 0.0434(16) -0.0006(13) -0.0096(15) -0.0141(16)
O3 0.0678(17) 0.0554(15) 0.0468(15) -0.0094(12) -0.0103(12) -0.0108(13)
O4 0.0557(17) 0.085(2) 0.0685(18) -0.0020(15) 0.0105(14) -0.0136(15)
O5 0.105(2) 0.0638(18) 0.0686(19) -0.0281(15) 0.0160(16) -0.0220(17)
O6 0.0562(16) 0.0527(16) 0.0777(19) 0.0165(14) -0.0037(14) -0.0074(13)
O7 0.0565(17) 0.0664(17) 0.0646(17) 0.0055(13) -0.0095(13) -0.0231(14)
S1 0.0603(6) 0.0460(6) 0.0546(6) 0.0017(4) -0.0028(5) -0.0146(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C7 119.8(4)
C2 C1 S1 119.6(3)
C7 C1 S1 120.6(3)
C1 C2 C3 119.7(4)
C1 C2 H2 120.1
C3 C2 H2 120.1
C4 C3 C2 121.7(4)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C6 117.5(4)
C3 C4 C5 121.1(4)
C6 C4 C5 121.4(4)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 C7 122.1(4)
C4 C6 H6 119.0
C7 C6 H6 119.0
C1 C7 C6 119.2(4)
C1 C7 H7 120.4
C6 C7 H7 120.4
O3 C8 C9 106.0(3)
O3 C8 H8A 110.5
C9 C8 H8A 110.5
O3 C8 H8B 110.5
C9 C8 H8B 110.5
H8A C8 H8B 108.7
C8 C9 C13 115.9(3)
C8 C9 C10 103.7(3)
C13 C9 C10 104.6(3)
C8 C9 H9 110.7
C13 C9 H9 110.7
C10 C9 H9 110.7
N1 C10 C11 111.2(2)
N1 C10 C9 106.3(3)
C11 C10 C9 107.0(3)
N1 C10 H10 110.7
C11 C10 H10 110.7
C9 C10 H10 110.7
C10 C11 C14 116.8(3)
C10 C11 C12 103.1(2)
C14 C11 C12 118.0(3)
C10 C11 H11 106.0
C14 C11 H11 106.0
C12 C11 H11 106.0
C25 C12 C22 109.9(3)
C25 C12 C13 109.8(3)
C22 C12 C13 111.3(3)
C25 C12 C11 113.2(3)
C22 C12 C11 111.7(3)
C13 C12 C11 100.7(2)
C9 C13 C12 107.3(3)
C9 C13 H13A 110.3
C12 C13 H13A 110.3
C9 C13 H13B 110.3
C12 C13 H13B 110.3
H13A C13 H13B 108.5
C16 C14 C15 113.0(3)
C16 C14 C11 110.6(3)
C15 C14 C11 114.6(3)
C16 C14 H14 106.0
C15 C14 H14 106.0
C11 C14 H14 106.0
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C21 C16 C17 116.1(4)
C21 C16 C14 120.0(3)
C17 C16 C14 123.9(3)
C18 C17 C16 122.2(4)
C18 C17 H17 118.9
C16 C17 H17 118.9
C19 C18 C17 119.9(4)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C20 119.7(4)
C18 C19 H19 120.1
C20 C19 H19 120.2
C19 C20 C21 120.1(4)
C19 C20 H20 120.0
C21 C20 H20 120.0
C20 C21 C16 122.0(4)
C20 C21 H21 119.0
C16 C21 H21 119.0
O4 C22 O5 124.8(4)
O4 C22 C12 124.7(4)
O5 C22 C12 110.5(3)
C24 C23 O5 111.7(5)
C24 C23 H23A 109.3
O5 C23 H23A 109.3
C24 C23 H23B 109.3
O5 C23 H23B 109.3
H23A C23 H23B 107.9
C23 C24 H24A 109.5
C23 C24 H24B 109.5
H24A C24 H24B 109.5
C23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
O7 C25 O6 123.9(3)
O7 C25 C12 126.1(3)
O6 C25 C12 110.0(3)
O6 C26 C27 108.7(4)
O6 C26 H26A 110.0
C27 C26 H26A 110.0
O6 C26 H26B 110.0
C27 C26 H26B 110.0
H26A C26 H26B 108.3
C26 C27 H27A 109.5
C26 C27 H27B 109.5
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
O3 N1 C10 105.4(2)
O3 N1 S1 108.97(19)
C10 N1 S1 114.9(2)
N1 O3 C8 107.7(2)
C22 O5 C23 118.3(4)
C25 O6 C26 118.1(3)
O2 S1 O1 118.61(18)
O2 S1 N1 103.61(15)
O1 S1 N1 113.04(16)
O2 S1 C1 110.92(17)
O1 S1 C1 108.55(17)
N1 S1 C1 100.61(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(5)
C1 C7 1.373(5)
C1 S1 1.751(4)
C2 C3 1.377(6)
C2 H2 0.9300
C3 C4 1.368(6)
C3 H3 0.9300
C4 C6 1.372(6)
C4 C5 1.511(6)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C7 1.376(5)
C6 H6 0.9300
C7 H7 0.9300
C8 O3 1.445(4)
C8 C9 1.517(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C13 1.530(5)
C9 C10 1.544(5)
C9 H9 0.9800
C10 N1 1.481(4)
C10 C11 1.532(4)
C10 H10 0.9800
C11 C14 1.552(4)
C11 C12 1.564(4)
C11 H11 0.9800
C12 C25 1.511(4)
C12 C22 1.520(5)
C12 C13 1.535(5)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C16 1.517(5)
C14 C15 1.534(5)
C14 H14 0.9800
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C21 1.386(5)
C16 C17 1.389(5)
C17 C18 1.375(6)
C17 H17 0.9300
C18 C19 1.361(6)
C18 H18 0.9300
C19 C20 1.371(6)
C19 H19 0.9300
C20 C21 1.373(6)
C20 H20 0.9300
C21 H21 0.9300
C22 O4 1.197(4)
C22 O5 1.340(5)
C23 C24 1.402(7)
C23 O5 1.463(5)
C23 H23A 0.9700
C23 H23B 0.9700
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C25 O7 1.199(4)
C25 O6 1.328(4)
C26 O6 1.440(4)
C26 C27 1.442(6)
C26 H26A 0.9700
C26 H26B 0.9700
C27 H27A 0.9600
C27 H27B 0.9600
C27 H27C 0.9600
N1 O3 1.430(3)
N1 S1 1.686(3)
O1 S1 1.431(3)
O2 S1 1.431(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C1 C2 C3 1.0(6)
S1 C1 C2 C3 178.2(3)
C1 C2 C3 C4 -0.3(7)
C2 C3 C4 C6 -0.8(7)
C2 C3 C4 C5 -179.6(4)
C3 C4 C6 C7 1.2(7)
C5 C4 C6 C7 -180.0(4)
C2 C1 C7 C6 -0.6(6)
S1 C1 C7 C6 -177.8(3)
C4 C6 C7 C1 -0.5(6)
O3 C8 C9 C13 98.6(3)
O3 C8 C9 C10 -15.4(4)
C8 C9 C10 N1 -4.6(3)
C13 C9 C10 N1 -126.4(3)
C8 C9 C10 C11 114.4(3)
C13 C9 C10 C11 -7.5(3)
N1 C10 C11 C14 -82.8(3)
C9 C10 C11 C14 161.5(3)
N1 C10 C11 C12 146.1(3)
C9 C10 C11 C12 30.4(3)
C10 C11 C12 C25 -157.9(3)
C14 C11 C12 C25 71.7(4)
C10 C11 C12 C22 77.5(3)
C14 C11 C12 C22 -52.9(4)
C10 C11 C12 C13 -40.8(3)
C14 C11 C12 C13 -171.2(3)
C8 C9 C13 C12 -132.6(3)
C10 C9 C13 C12 -19.1(3)
C25 C12 C13 C9 156.9(3)
C22 C12 C13 C9 -81.2(3)
C11 C12 C13 C9 37.3(3)
C10 C11 C14 C16 91.3(3)
C12 C11 C14 C16 -144.9(3)
C10 C11 C14 C15 -37.9(4)
C12 C11 C14 C15 85.9(4)
C15 C14 C16 C21 -158.3(4)
C11 C14 C16 C21 71.7(4)
C15 C14 C16 C17 22.4(5)
C11 C14 C16 C17 -107.6(4)
C21 C16 C17 C18 0.2(6)
C14 C16 C17 C18 179.5(4)
C16 C17 C18 C19 0.2(7)
C17 C18 C19 C20 -0.3(7)
C18 C19 C20 C21 -0.2(8)
C19 C20 C21 C16 0.6(8)
C17 C16 C21 C20 -0.6(6)
C14 C16 C21 C20 -180.0(4)
C25 C12 C22 O4 142.8(4)
C13 C12 C22 O4 20.9(5)
C11 C12 C22 O4 -90.8(4)
C25 C12 C22 O5 -39.7(4)
C13 C12 C22 O5 -161.6(3)
C11 C12 C22 O5 86.8(3)
C22 C12 C25 O7 127.6(4)
C13 C12 C25 O7 -109.6(4)
C11 C12 C25 O7 2.0(5)
C22 C12 C25 O6 -54.1(4)
C13 C12 C25 O6 68.7(3)
C11 C12 C25 O6 -179.6(3)
C11 C10 N1 O3 -93.1(3)
C9 C10 N1 O3 23.1(3)
C11 C10 N1 S1 146.9(2)
C9 C10 N1 S1 -96.9(3)
C10 N1 O3 C8 -34.0(3)
S1 N1 O3 C8 89.8(3)
C9 C8 O3 N1 31.1(4)
O4 C22 O5 C23 2.0(6)
C12 C22 O5 C23 -175.5(4)
C24 C23 O5 C22 -102.7(5)
O7 C25 O6 C26 -4.0(5)
C12 C25 O6 C26 177.6(3)
C27 C26 O6 C25 -153.1(4)
O3 N1 S1 O2 -178.1(2)
C10 N1 S1 O2 -60.1(3)
O3 N1 S1 O1 -48.5(2)
C10 N1 S1 O1 69.5(3)
O3 N1 S1 C1 67.1(2)
C10 N1 S1 C1 -174.9(2)
C2 C1 S1 O2 -52.8(4)
C7 C1 S1 O2 124.3(3)
C2 C1 S1 O1 175.2(3)
C7 C1 S1 O1 -7.7(4)
C2 C1 S1 N1 56.3(3)
C7 C1 S1 N1 -126.6(3)
|
1502018.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502018.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502018
loop_
_publ_author_name
'Witek, Jason A.'
'Weinreb, Steven M.'
_publ_section_title
;
Investigation of the stereochemistry of intermolecular conjugate
additions of nucleophiles to acyclic nitrosoalkenes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1258
_journal_page_last 1260
_journal_paper_doi 10.1021/ol2000793
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C27 H33 N O8 S'
_chemical_formula_sum 'C27 H33 N O8 S'
_chemical_formula_weight 531.60
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 78.500(3)
_cell_angle_beta 67.748(3)
_cell_angle_gamma 74.424(3)
_cell_formula_units_Z 2
_cell_length_a 10.5885(12)
_cell_length_b 11.5490(13)
_cell_length_c 12.6474(14)
_cell_measurement_reflns_used 3775
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 26.361
_cell_measurement_theta_min 2.398
_cell_volume 1370.6(3)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0205
_diffrn_reflns_av_sigmaI/netI 0.0348
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 12930
_diffrn_reflns_theta_full 28.29
_diffrn_reflns_theta_max 28.29
_diffrn_reflns_theta_min 1.75
_exptl_absorpt_coefficient_mu 0.167
_exptl_absorpt_correction_T_max 0.9642
_exptl_absorpt_correction_T_min 0.9548
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.288
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 564
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.22
_refine_diff_density_max 0.438
_refine_diff_density_min -0.241
_refine_diff_density_rms 0.049
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment noref
_refine_ls_matrix_type full
_refine_ls_number_parameters 338
_refine_ls_number_reflns 6609
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.052
_refine_ls_R_factor_all 0.0821
_refine_ls_R_factor_gt 0.0600
_refine_ls_shift/su_max 0.009
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+0.1663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1640
_refine_ls_wR_factor_ref 0.1796
_reflns_number_gt 4691
_reflns_number_total 6609
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000793_si_002.cif
_cod_data_source_block jaw2s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502018
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5070(2) 1.05606(19) 0.21140(18) 0.0521(5) Uani 1 1 d .
C2 C 0.5208(3) 1.1502(2) 0.2548(2) 0.0642(6) Uani 1 1 d .
H2 H 0.6072 1.1537 0.2555 0.077 Uiso 1 1 calc R
C3 C 0.4045(3) 1.2397(2) 0.2973(2) 0.0680(7) Uani 1 1 d .
H3 H 0.4136 1.3035 0.3267 0.082 Uiso 1 1 calc R
C4 C 0.2765(3) 1.2367(2) 0.2970(2) 0.0608(6) Uani 1 1 d .
C5 C 0.2657(3) 1.1425(3) 0.2516(3) 0.0845(9) Uani 1 1 d .
H5 H 0.1794 1.1395 0.2502 0.101 Uiso 1 1 calc R
C6 C 0.3806(3) 1.0524(3) 0.2080(3) 0.0791(8) Uani 1 1 d .
H6 H 0.3720 0.9898 0.1767 0.095 Uiso 1 1 calc R
C7 C 0.1477(3) 1.3322(3) 0.3484(3) 0.0865(9) Uani 1 1 d .
H7A H 0.1191 1.3192 0.4307 0.130 Uiso 1 1 calc R
H7B H 0.0735 1.3268 0.3247 0.130 Uiso 1 1 calc R
H7C H 0.1689 1.4110 0.3221 0.130 Uiso 1 1 calc R
C8 C 0.7286(3) 0.7978(2) 0.3776(2) 0.0725(7) Uani 1 1 d .
H8A H 0.7194 0.7730 0.4577 0.087 Uiso 1 1 calc R
H8B H 0.7846 0.8589 0.3476 0.087 Uiso 1 1 calc R
C9 C 0.7954(2) 0.6899(2) 0.30831(19) 0.0515(5) Uani 1 1 d .
H9 H 0.8925 0.6924 0.2606 0.062 Uiso 1 1 calc R
C10 C 0.70544(19) 0.70572(16) 0.23188(16) 0.0409(4) Uani 1 1 d .
H10 H 0.7637 0.7078 0.1504 0.049 Uiso 1 1 calc R
C11 C 0.63474(18) 0.59698(17) 0.26979(15) 0.0390(4) Uani 1 1 d .
H11 H 0.5516 0.6164 0.3377 0.047 Uiso 1 1 calc R
C12 C 0.74161(19) 0.49599(17) 0.31095(16) 0.0426(4) Uani 1 1 d .
C13 C 0.7861(2) 0.5656(2) 0.37805(18) 0.0508(5) Uani 1 1 d .
H13A H 0.7176 0.5741 0.4546 0.061 Uiso 1 1 calc R
H13B H 0.8758 0.5238 0.3846 0.061 Uiso 1 1 calc R
C14 C 0.58609(19) 0.56586(18) 0.18073(16) 0.0439(4) Uani 1 1 d .
H14 H 0.5797 0.4806 0.1988 0.053 Uiso 1 1 calc R
C15 C 0.4430(2) 0.64092(18) 0.18444(16) 0.0442(4) Uani 1 1 d .
C16 C 0.4241(3) 0.7397(2) 0.1053(2) 0.0606(6) Uani 1 1 d .
H16 H 0.5012 0.7619 0.0462 0.073 Uiso 1 1 calc R
C17 C 0.2911(3) 0.8057(2) 0.1136(3) 0.0728(7) Uani 1 1 d .
H17 H 0.2798 0.8719 0.0600 0.087 Uiso 1 1 calc R
C18 C 0.1766(3) 0.7748(2) 0.1994(3) 0.0749(8) Uani 1 1 d .
H18 H 0.0877 0.8197 0.2044 0.090 Uiso 1 1 calc R
C19 C 0.1933(3) 0.6767(3) 0.2786(3) 0.0754(8) Uani 1 1 d .
H19 H 0.1157 0.6550 0.3375 0.090 Uiso 1 1 calc R
C20 C 0.3256(2) 0.6107(2) 0.2702(2) 0.0598(6) Uani 1 1 d .
H20 H 0.3360 0.5441 0.3238 0.072 Uiso 1 1 calc R
C21 C 0.6861(3) 0.5180(3) -0.0124(2) 0.0792(8) Uani 1 1 d .
H21A H 0.6721 0.4379 0.0201 0.119 Uiso 1 1 calc R
H21B H 0.7720 0.5130 -0.0766 0.119 Uiso 1 1 calc R
H21C H 0.6099 0.5618 -0.0377 0.119 Uiso 1 1 calc R
C22 C 0.6758(2) 0.39286(18) 0.38860(16) 0.0459(5) Uani 1 1 d .
C23 C 0.7252(3) 0.2032(2) 0.4967(3) 0.0825(9) Uani 1 1 d .
H23A H 0.7059 0.2098 0.5768 0.099 Uiso 1 1 calc R
H23B H 0.6398 0.1961 0.4891 0.099 Uiso 1 1 calc R
C24 C 0.8266(7) 0.1020(4) 0.4638(6) 0.226(4) Uani 1 1 d .
H24A H 0.8567 0.1025 0.3820 0.339 Uiso 1 1 calc R
H24B H 0.7896 0.0312 0.5010 0.339 Uiso 1 1 calc R
H24C H 0.9045 0.1014 0.4854 0.339 Uiso 1 1 calc R
C25 C 0.8678(2) 0.44695(19) 0.20955(17) 0.0491(5) Uani 1 1 d .
C26 C 0.9688(3) 0.2992(3) 0.0793(2) 0.0824(9) Uani 1 1 d .
H26A H 0.9689 0.3498 0.0082 0.099 Uiso 1 1 calc R
H26B H 1.0568 0.2934 0.0893 0.099 Uiso 1 1 calc R
C27 C 0.9524(4) 0.1820(4) 0.0751(4) 0.1284(17) Uani 1 1 d .
H27A H 0.9619 0.1303 0.1424 0.193 Uiso 1 1 calc R
H27B H 1.0226 0.1489 0.0078 0.193 Uiso 1 1 calc R
H27C H 0.8615 0.1879 0.0723 0.193 Uiso 1 1 calc R
N1 N 0.60286(17) 0.82097(14) 0.25580(13) 0.0438(4) Uani 1 1 d .
O1 O 0.77289(17) 0.96859(16) 0.16410(16) 0.0739(5) Uani 1 1 d .
O2 O 0.6583(2) 0.90989(15) 0.05279(13) 0.0746(5) Uani 1 1 d .
O3 O 0.59250(17) 0.84429(13) 0.36616(12) 0.0579(4) Uani 1 1 d .
O4 O 0.69240(15) 0.57879(15) 0.07197(12) 0.0556(4) Uani 1 1 d .
O5 O 0.55619(16) 0.38716(15) 0.41459(14) 0.0611(4) Uani 1 1 d .
O6 O 0.76917(16) 0.31191(14) 0.42618(14) 0.0649(5) Uani 1 1 d .
O7 O 0.85159(17) 0.35226(15) 0.17691(14) 0.0671(5) Uani 1 1 d .
O8 O 0.96938(16) 0.49014(16) 0.16613(14) 0.0675(5) Uani 1 1 d .
S1 S 0.65259(6) 0.93971(5) 0.15896(5) 0.05410(18) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0613(13) 0.0427(11) 0.0515(12) 0.0009(9) -0.0210(10) -0.0119(10)
C2 0.0594(14) 0.0576(14) 0.0787(16) -0.0156(12) -0.0229(12) -0.0129(11)
C3 0.0690(15) 0.0575(14) 0.0822(17) -0.0213(12) -0.0260(13) -0.0110(12)
C4 0.0661(15) 0.0520(13) 0.0636(14) 0.0004(10) -0.0323(12) -0.0019(11)
C5 0.0747(18) 0.0792(19) 0.119(2) -0.0199(17) -0.0614(18) -0.0009(15)
C6 0.0841(19) 0.0642(16) 0.110(2) -0.0258(16) -0.0565(18) -0.0046(14)
C7 0.0731(18) 0.0753(19) 0.105(2) -0.0167(16) -0.0389(17) 0.0116(15)
C8 0.099(2) 0.0598(15) 0.0768(17) -0.0108(13) -0.0509(16) -0.0135(14)
C9 0.0488(11) 0.0539(12) 0.0587(13) -0.0027(10) -0.0231(10) -0.0177(10)
C10 0.0389(9) 0.0418(10) 0.0394(9) -0.0031(7) -0.0090(7) -0.0118(8)
C11 0.0342(9) 0.0421(10) 0.0370(9) -0.0033(7) -0.0071(7) -0.0105(7)
C12 0.0370(9) 0.0448(10) 0.0402(10) -0.0013(8) -0.0079(7) -0.0097(8)
C13 0.0470(11) 0.0568(12) 0.0503(11) -0.0006(9) -0.0209(9) -0.0116(9)
C14 0.0409(10) 0.0474(11) 0.0411(10) -0.0054(8) -0.0071(8) -0.0157(8)
C15 0.0452(10) 0.0481(11) 0.0438(10) -0.0025(8) -0.0171(8) -0.0166(9)
C16 0.0612(14) 0.0671(14) 0.0588(13) 0.0136(11) -0.0269(11) -0.0279(12)
C17 0.0771(17) 0.0617(15) 0.0913(19) 0.0201(13) -0.0509(15) -0.0224(13)
C18 0.0571(14) 0.0676(16) 0.104(2) -0.0020(15) -0.0405(15) -0.0065(12)
C19 0.0451(12) 0.0850(19) 0.0847(18) 0.0076(15) -0.0162(12) -0.0168(12)
C20 0.0470(12) 0.0595(13) 0.0634(14) 0.0108(11) -0.0149(10) -0.0145(10)
C21 0.0653(15) 0.121(2) 0.0575(14) -0.0389(15) -0.0064(12) -0.0299(16)
C22 0.0458(11) 0.0450(10) 0.0390(10) -0.0026(8) -0.0066(8) -0.0105(9)
C23 0.0810(18) 0.0535(14) 0.0841(18) 0.0234(13) -0.0128(14) -0.0130(13)
C24 0.216(6) 0.064(2) 0.232(6) 0.033(3) 0.061(5) 0.000(3)
C25 0.0416(10) 0.0461(11) 0.0470(11) 0.0025(9) -0.0080(8) -0.0052(9)
C26 0.0757(17) 0.0748(17) 0.0641(16) -0.0187(13) 0.0141(13) -0.0115(14)
C27 0.114(3) 0.109(3) 0.130(3) -0.071(3) 0.035(2) -0.042(2)
N1 0.0466(9) 0.0407(8) 0.0380(8) -0.0024(6) -0.0081(7) -0.0104(7)
O1 0.0549(9) 0.0625(10) 0.0915(13) -0.0093(9) -0.0017(8) -0.0260(8)
O2 0.1122(14) 0.0549(9) 0.0435(9) 0.0004(7) -0.0152(9) -0.0177(9)
O3 0.0727(10) 0.0520(9) 0.0423(8) -0.0086(6) -0.0120(7) -0.0112(8)
O4 0.0470(8) 0.0799(11) 0.0406(7) -0.0146(7) -0.0043(6) -0.0247(7)
O5 0.0504(9) 0.0635(10) 0.0630(10) 0.0074(7) -0.0117(7) -0.0239(7)
O6 0.0531(9) 0.0532(9) 0.0688(10) 0.0174(7) -0.0132(8) -0.0086(7)
O7 0.0643(10) 0.0579(10) 0.0564(9) -0.0149(7) 0.0100(7) -0.0151(8)
O8 0.0414(8) 0.0791(11) 0.0660(10) -0.0025(8) -0.0007(7) -0.0172(8)
S1 0.0610(3) 0.0433(3) 0.0479(3) 0.0008(2) -0.0067(2) -0.0168(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.4(2)
C6 C1 S1 119.55(18)
C2 C1 S1 120.02(19)
C1 C2 C3 119.1(2)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 121.6(2)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 118.3(2)
C3 C4 C7 121.5(2)
C5 C4 C7 120.2(3)
C4 C5 C6 121.2(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 119.4(2)
C1 C6 H6 120.3
C5 C6 H6 120.3
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O3 C8 C9 105.67(18)
O3 C8 H8A 110.6
C9 C8 H8A 110.6
O3 C8 H8B 110.6
C9 C8 H8B 110.6
H8A C8 H8B 108.7
C8 C9 C13 115.55(19)
C8 C9 C10 103.83(18)
C13 C9 C10 105.37(15)
C8 C9 H9 110.6
C13 C9 H9 110.6
C10 C9 H9 110.6
N1 C10 C11 111.91(14)
N1 C10 C9 106.09(16)
C11 C10 C9 106.20(15)
N1 C10 H10 110.8
C11 C10 H10 110.8
C9 C10 H10 110.8
C10 C11 C14 115.49(15)
C10 C11 C12 103.00(14)
C14 C11 C12 116.32(16)
C10 C11 H11 107.2
C14 C11 H11 107.2
C12 C11 H11 107.2
C22 C12 C25 110.27(16)
C22 C12 C13 111.14(16)
C25 C12 C13 109.87(16)
C22 C12 C11 112.32(15)
C25 C12 C11 111.45(15)
C13 C12 C11 101.50(15)
C9 C13 C12 105.52(16)
C9 C13 H13A 110.6
C12 C13 H13A 110.6
C9 C13 H13B 110.6
C12 C13 H13B 110.6
H13A C13 H13B 108.8
O4 C14 C15 113.69(16)
O4 C14 C11 107.03(14)
C15 C14 C11 112.18(16)
O4 C14 H14 107.9
C15 C14 H14 107.9
C11 C14 H14 107.9
C20 C15 C16 117.8(2)
C20 C15 C14 119.24(18)
C16 C15 C14 122.93(18)
C15 C16 C17 120.4(2)
C15 C16 H16 119.8
C17 C16 H16 119.8
C18 C17 C16 120.8(2)
C18 C17 H17 119.6
C16 C17 H17 119.6
C17 C18 C19 119.6(2)
C17 C18 H18 120.2
C19 C18 H18 120.2
C18 C19 C20 119.7(2)
C18 C19 H19 120.2
C20 C19 H19 120.2
C19 C20 C15 121.7(2)
C19 C20 H20 119.2
C15 C20 H20 119.2
O4 C21 H21A 109.5
O4 C21 H21B 109.5
H21A C21 H21B 109.5
O4 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
O5 C22 O6 124.75(18)
O5 C22 C12 125.12(19)
O6 C22 C12 110.10(16)
C24 C23 O6 110.8(3)
C24 C23 H23A 109.5
O6 C23 H23A 109.5
C24 C23 H23B 109.5
O6 C23 H23B 109.5
H23A C23 H23B 108.1
C23 C24 H24A 109.5
C23 C24 H24B 109.5
H24A C24 H24B 109.5
C23 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
O8 C25 O7 124.6(2)
O8 C25 C12 123.4(2)
O7 C25 C12 112.04(17)
C27 C26 O7 108.1(2)
C27 C26 H26A 110.1
O7 C26 H26A 110.1
C27 C26 H26B 110.1
O7 C26 H26B 110.1
H26A C26 H26B 108.4
C26 C27 H27A 109.5
C26 C27 H27B 109.5
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
O3 N1 C10 105.99(14)
O3 N1 S1 108.07(11)
C10 N1 S1 113.32(11)
N1 O3 C8 107.80(16)
C21 O4 C14 113.79(17)
C22 O6 C23 117.13(19)
C25 O7 C26 115.56(19)
O2 S1 O1 118.66(12)
O2 S1 N1 104.30(9)
O1 S1 N1 112.37(10)
O2 S1 C1 110.74(11)
O1 S1 C1 108.78(11)
N1 S1 C1 100.44(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.367(3)
C1 C2 1.375(3)
C1 S1 1.758(2)
C2 C3 1.381(3)
C2 H2 0.9300
C3 C4 1.366(4)
C3 H3 0.9300
C4 C5 1.376(4)
C4 C7 1.519(4)
C5 C6 1.381(4)
C5 H5 0.9300
C6 H6 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 O3 1.448(3)
C8 C9 1.522(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C13 1.534(3)
C9 C10 1.552(3)
C9 H9 0.9800
C10 N1 1.476(2)
C10 C11 1.536(2)
C10 H10 0.9800
C11 C14 1.537(3)
C11 C12 1.551(3)
C11 H11 0.9800
C12 C22 1.526(3)
C12 C25 1.528(3)
C12 C13 1.538(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 O4 1.420(2)
C14 C15 1.519(3)
C14 H14 0.9800
C15 C20 1.380(3)
C15 C16 1.384(3)
C16 C17 1.385(4)
C16 H16 0.9300
C17 C18 1.362(4)
C17 H17 0.9300
C18 C19 1.376(4)
C18 H18 0.9300
C19 C20 1.379(3)
C19 H19 0.9300
C20 H20 0.9300
C21 O4 1.419(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 O5 1.199(2)
C22 O6 1.327(3)
C23 C24 1.368(5)
C23 O6 1.464(3)
C23 H23A 0.9700
C23 H23B 0.9700
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C25 O8 1.200(2)
C25 O7 1.315(3)
C26 C27 1.423(4)
C26 O7 1.474(3)
C26 H26A 0.9700
C26 H26B 0.9700
C27 H27A 0.9600
C27 H27B 0.9600
C27 H27C 0.9600
N1 O3 1.432(2)
N1 S1 1.6993(16)
O1 S1 1.4275(18)
O2 S1 1.4272(18)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.4(4)
S1 C1 C2 C3 -179.0(2)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -0.9(4)
C2 C3 C4 C7 177.3(3)
C3 C4 C5 C6 0.5(5)
C7 C4 C5 C6 -177.8(3)
C2 C1 C6 C5 -1.8(4)
S1 C1 C6 C5 178.6(2)
C4 C5 C6 C1 0.8(5)
O3 C8 C9 C13 -98.8(2)
O3 C8 C9 C10 16.1(2)
C8 C9 C10 N1 3.4(2)
C13 C9 C10 N1 125.33(16)
C8 C9 C10 C11 -115.80(19)
C13 C9 C10 C11 6.1(2)
N1 C10 C11 C14 86.70(19)
C9 C10 C11 C14 -157.95(16)
N1 C10 C11 C12 -145.41(15)
C9 C10 C11 C12 -30.06(18)
C10 C11 C12 C22 160.94(15)
C14 C11 C12 C22 -71.7(2)
C10 C11 C12 C25 -74.74(19)
C14 C11 C12 C25 52.6(2)
C10 C11 C12 C13 42.17(17)
C14 C11 C12 C13 169.53(15)
C8 C9 C13 C12 134.58(19)
C10 C9 C13 C12 20.6(2)
C22 C12 C13 C9 -158.59(17)
C25 C12 C13 C9 79.1(2)
C11 C12 C13 C9 -38.97(19)
C10 C11 C14 O4 41.0(2)
C12 C11 C14 O4 -79.92(19)
C10 C11 C14 C15 -84.36(19)
C12 C11 C14 C15 154.72(15)
O4 C14 C15 C20 160.52(19)
C11 C14 C15 C20 -77.9(2)
O4 C14 C15 C16 -19.7(3)
C11 C14 C15 C16 101.9(2)
C20 C15 C16 C17 0.5(3)
C14 C15 C16 C17 -179.3(2)
C15 C16 C17 C18 -0.1(4)
C16 C17 C18 C19 -0.1(5)
C17 C18 C19 C20 -0.1(5)
C18 C19 C20 C15 0.5(4)
C16 C15 C20 C19 -0.7(4)
C14 C15 C20 C19 179.1(2)
C25 C12 C22 O5 -123.7(2)
C13 C12 C22 O5 114.2(2)
C11 C12 C22 O5 1.2(3)
C25 C12 C22 O6 58.2(2)
C13 C12 C22 O6 -63.9(2)
C11 C12 C22 O6 -176.86(16)
C22 C12 C25 O8 -146.7(2)
C13 C12 C25 O8 -23.8(3)
C11 C12 C25 O8 87.9(2)
C22 C12 C25 O7 32.9(2)
C13 C12 C25 O7 155.70(18)
C11 C12 C25 O7 -92.6(2)
C11 C10 N1 O3 93.43(17)
C9 C10 N1 O3 -21.98(17)
C11 C10 N1 S1 -148.21(13)
C9 C10 N1 S1 96.38(15)
C10 N1 O3 C8 33.4(2)
S1 N1 O3 C8 -88.34(17)
C9 C8 O3 N1 -31.0(2)
C15 C14 O4 C21 -74.5(2)
C11 C14 O4 C21 161.0(2)
O5 C22 O6 C23 5.3(3)
C12 C22 O6 C23 -176.6(2)
C24 C23 O6 C22 136.0(5)
O8 C25 O7 C26 -0.5(4)
C12 C25 O7 C26 -180.0(2)
C27 C26 O7 C25 164.6(3)
O3 N1 S1 O2 -179.22(13)
C10 N1 S1 O2 63.64(16)
O3 N1 S1 O1 50.98(15)
C10 N1 S1 O1 -66.16(16)
O3 N1 S1 C1 -64.48(14)
C10 N1 S1 C1 178.38(14)
C6 C1 S1 O2 43.7(2)
C2 C1 S1 O2 -135.9(2)
C6 C1 S1 O1 175.8(2)
C2 C1 S1 O1 -3.8(2)
C6 C1 S1 N1 -66.1(2)
C2 C1 S1 N1 114.3(2)
|
1502019.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502019.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502019
loop_
_publ_author_name
'Witek, Jason A.'
'Weinreb, Steven M.'
_publ_section_title
;
Investigation of the stereochemistry of intermolecular conjugate
additions of nucleophiles to acyclic nitrosoalkenes.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1258
_journal_page_last 1260
_journal_paper_doi 10.1021/ol2000793
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C25 H36 N2 O9 S'
_chemical_formula_sum 'C25 H36 N2 O9 S'
_chemical_formula_weight 540.62
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 95.649(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 10.4925(9)
_cell_length_b 15.2878(12)
_cell_length_c 17.4611(14)
_cell_measurement_reflns_used 2191
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 26.880
_cell_measurement_theta_min 2.174
_cell_volume 2787.3(4)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0269
_diffrn_reflns_av_sigmaI/netI 0.0498
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 13036
_diffrn_reflns_theta_full 28.29
_diffrn_reflns_theta_max 28.29
_diffrn_reflns_theta_min 1.77
_exptl_absorpt_coefficient_mu 0.168
_exptl_absorpt_correction_T_max 0.990
_exptl_absorpt_correction_T_min 0.978
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.288
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1152
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.04
_refine_diff_density_max 0.392
_refine_diff_density_min -0.164
_refine_diff_density_rms 0.046
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.025
_refine_ls_hydrogen_treatment noref
_refine_ls_matrix_type full
_refine_ls_number_parameters 340
_refine_ls_number_reflns 6612
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.025
_refine_ls_R_factor_all 0.1062
_refine_ls_R_factor_gt 0.0629
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.2594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1437
_refine_ls_wR_factor_ref 0.1665
_reflns_number_gt 4099
_reflns_number_total 6612
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000793_si_003.cif
_cod_data_source_block jaw3s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/n
_cod_database_code 1502019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1633(2) 0.41266(15) 1.11633(13) 0.0440(5) Uani 1 1 d .
C2 C 0.0369(2) 0.43967(17) 1.10840(14) 0.0533(6) Uani 1 1 d .
H2 H -0.0113 0.4366 1.0608 0.064 Uiso 1 1 calc R
C3 C -0.0166(2) 0.47107(17) 1.17145(15) 0.0560(7) Uani 1 1 d .
H3 H -0.1012 0.4900 1.1671 0.067 Uiso 1 1 calc R
C4 C 0.0558(2) 0.47415(15) 1.24062(14) 0.0490(6) Uani 1 1 d .
C5 C 0.1813(3) 0.44823(18) 1.25018(14) 0.0588(7) Uani 1 1 d .
H5 H 0.2283 0.4511 1.2981 0.071 Uiso 1 1 calc R
C6 C 0.2362(2) 0.41763(18) 1.18630(14) 0.0564(7) Uani 1 1 d .
H6 H 0.3217 0.4006 1.1906 0.068 Uiso 1 1 calc R
C7 C 0.3413(3) 0.1811(2) 1.05531(19) 0.0928(12) Uani 1 1 d .
H7A H 0.3618 0.1264 1.0819 0.111 Uiso 1 1 calc R
H7B H 0.4156 0.2191 1.0619 0.111 Uiso 1 1 calc R
C8 C 0.3023(2) 0.16499(17) 0.97093(15) 0.0571(7) Uani 1 1 d .
H8 H 0.3736 0.1782 0.9405 0.069 Uiso 1 1 calc R
C9 C 0.1910(2) 0.22974(15) 0.95109(12) 0.0424(5) Uani 1 1 d .
H9 H 0.2120 0.2714 0.9115 0.051 Uiso 1 1 calc R
C10 C 0.0727(2) 0.17522(14) 0.92288(12) 0.0402(5) Uani 1 1 d .
H10 H 0.0358 0.1563 0.9696 0.048 Uiso 1 1 calc R
C11 C 0.1320(2) 0.09124(14) 0.89012(12) 0.0403(5) Uani 1 1 d .
C12 C 0.2474(2) 0.07512(16) 0.95007(13) 0.0494(6) Uani 1 1 d .
H12A H 0.2203 0.0462 0.9952 0.059 Uiso 1 1 calc R
H12B H 0.3108 0.0388 0.9286 0.059 Uiso 1 1 calc R
C13 C 0.0413(2) 0.01337(15) 0.88568(13) 0.0453(6) Uani 1 1 d .
C14 C 0.0261(3) -0.13517(18) 0.84775(18) 0.0748(9) Uani 1 1 d .
H14A H -0.0472 -0.1225 0.8111 0.090 Uiso 1 1 calc R
H14B H -0.0049 -0.1566 0.8948 0.090 Uiso 1 1 calc R
C15 C 0.1086(4) -0.2022(2) 0.8157(2) 0.1019(12) Uani 1 1 d .
H15A H 0.1381 -0.1806 0.7689 0.153 Uiso 1 1 calc R
H15B H 0.0602 -0.2548 0.8052 0.153 Uiso 1 1 calc R
H15C H 0.1808 -0.2143 0.8523 0.153 Uiso 1 1 calc R
C16 C 0.1772(2) 0.10577(15) 0.81050(13) 0.0446(6) Uani 1 1 d .
C17 C 0.1173(3) 0.0865(2) 0.67609(13) 0.0639(7) Uani 1 1 d .
H17A H 0.2062 0.1029 0.6744 0.077 Uiso 1 1 calc R
H17B H 0.0641 0.1297 0.6475 0.077 Uiso 1 1 calc R
C18 C 0.0942(3) 0.0000(2) 0.64183(18) 0.0827(10) Uani 1 1 d .
H18A H 0.1498 -0.0419 0.6691 0.124 Uiso 1 1 calc R
H18B H 0.1112 0.0016 0.5888 0.124 Uiso 1 1 calc R
H18C H 0.0067 -0.0165 0.6451 0.124 Uiso 1 1 calc R
C19 C -0.0355(2) 0.22458(15) 0.87500(13) 0.0462(6) Uani 1 1 d .
H19 H -0.0960 0.1805 0.8525 0.055 Uiso 1 1 calc R
C20 C 0.0077(3) 0.27836(18) 0.80835(15) 0.0670(8) Uani 1 1 d .
H20A H 0.0596 0.3264 0.8284 0.100 Uiso 1 1 calc R
H20B H -0.0661 0.3005 0.7775 0.100 Uiso 1 1 calc R
H20C H 0.0566 0.2420 0.7773 0.100 Uiso 1 1 calc R
C21 C -0.1096(2) 0.28340(18) 0.92741(15) 0.0585(7) Uani 1 1 d .
H21A H -0.0768 0.2714 0.9803 0.070 Uiso 1 1 calc R
H21B H -0.0883 0.3437 0.9169 0.070 Uiso 1 1 calc R
C22 C -0.2543(2) 0.27662(18) 0.92234(17) 0.0632(7) Uani 1 1 d .
C23 C -0.2900(4) 0.1861(2) 0.9515(3) 0.1081(13) Uani 1 1 d .
H23A H -0.2544 0.1417 0.9211 0.162 Uiso 1 1 calc R
H23B H -0.3815 0.1804 0.9473 0.162 Uiso 1 1 calc R
H23C H -0.2564 0.1797 1.0043 0.162 Uiso 1 1 calc R
C24 C -0.3156(3) 0.2913(3) 0.8415(2) 0.1224(16) Uani 1 1 d .
H24A H -0.2959 0.3492 0.8250 0.184 Uiso 1 1 calc R
H24B H -0.4067 0.2848 0.8405 0.184 Uiso 1 1 calc R
H24C H -0.2831 0.2492 0.8076 0.184 Uiso 1 1 calc R
C25 C -0.3028(3) 0.3454(2) 0.9765(2) 0.0944(11) Uani 1 1 d .
H25A H -0.2613 0.3372 1.0275 0.142 Uiso 1 1 calc R
H25B H -0.3937 0.3393 0.9774 0.142 Uiso 1 1 calc R
H25C H -0.2838 0.4029 0.9585 0.142 Uiso 1 1 calc R
N1 N 0.17140(18) 0.27577(12) 1.02429(10) 0.0449(5) Uani 1 1 d .
N2 N -0.0027(3) 0.50824(15) 1.30837(14) 0.0618(6) Uani 1 1 d .
O1 O -0.1002(2) 0.55071(15) 1.29693(13) 0.0907(7) Uani 1 1 d .
O2 O 0.0494(2) 0.49138(16) 1.37169(13) 0.0881(7) Uani 1 1 d .
O3 O 0.17149(18) 0.42298(11) 0.96775(9) 0.0601(5) Uani 1 1 d .
O4 O 0.36727(16) 0.37973(13) 1.04822(10) 0.0679(5) Uani 1 1 d .
O5 O -0.06802(17) 0.01399(12) 0.90014(11) 0.0638(5) Uani 1 1 d .
O6 O 0.27925(17) 0.13459(13) 0.79938(10) 0.0663(5) Uani 1 1 d .
O7 O 0.08655(16) 0.08346(12) 0.75539(9) 0.0559(5) Uani 1 1 d .
O8 O 0.10140(17) -0.05713(11) 0.86332(10) 0.0584(5) Uani 1 1 d .
O9 O 0.2312(2) 0.22275(12) 1.08512(9) 0.0692(6) Uani 1 1 d .
S1 S 0.23144(6) 0.37727(4) 1.03305(3) 0.04773(19) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0431(13) 0.0405(13) 0.0480(13) -0.0002(10) 0.0022(10) -0.0034(11)
C2 0.0468(14) 0.0571(16) 0.0540(14) -0.0024(12) -0.0054(11) -0.0030(12)
C3 0.0444(14) 0.0538(16) 0.0701(17) -0.0010(13) 0.0071(13) -0.0002(12)
C4 0.0545(15) 0.0397(13) 0.0542(14) -0.0019(11) 0.0123(12) -0.0076(11)
C5 0.0599(17) 0.0685(18) 0.0472(14) -0.0032(13) 0.0010(12) -0.0018(14)
C6 0.0431(14) 0.0698(18) 0.0552(15) 0.0020(13) 0.0002(11) 0.0014(13)
C7 0.098(3) 0.071(2) 0.098(2) -0.0159(19) -0.048(2) 0.033(2)
C8 0.0403(14) 0.0586(17) 0.0702(17) -0.0053(13) -0.0062(12) 0.0082(12)
C9 0.0371(12) 0.0435(13) 0.0469(12) -0.0001(10) 0.0047(10) 0.0021(10)
C10 0.0385(12) 0.0426(13) 0.0401(11) -0.0009(10) 0.0072(9) 0.0016(10)
C11 0.0401(12) 0.0403(12) 0.0413(12) 0.0011(10) 0.0074(10) 0.0038(10)
C12 0.0458(14) 0.0507(15) 0.0516(13) 0.0008(11) 0.0044(11) 0.0114(12)
C13 0.0506(14) 0.0451(14) 0.0413(12) 0.0034(10) 0.0096(11) -0.0006(11)
C14 0.100(2) 0.0464(17) 0.0783(19) -0.0054(14) 0.0133(17) -0.0143(16)
C15 0.141(4) 0.054(2) 0.110(3) -0.0199(19) 0.006(2) 0.014(2)
C16 0.0417(13) 0.0426(14) 0.0507(13) 0.0017(10) 0.0115(11) 0.0049(11)
C17 0.0620(17) 0.091(2) 0.0404(13) 0.0055(14) 0.0123(12) 0.0020(15)
C18 0.094(2) 0.096(3) 0.0620(18) -0.0102(17) 0.0228(17) 0.0109(19)
C19 0.0396(13) 0.0470(14) 0.0508(13) -0.0070(11) -0.0017(10) 0.0041(11)
C20 0.0715(19) 0.0623(18) 0.0660(17) 0.0115(14) 0.0013(14) 0.0219(15)
C21 0.0467(15) 0.0562(16) 0.0714(16) -0.0119(13) -0.0005(12) 0.0096(12)
C22 0.0407(14) 0.0658(18) 0.0822(19) -0.0172(15) 0.0008(13) 0.0087(13)
C23 0.086(3) 0.093(3) 0.152(4) -0.032(3) 0.049(2) -0.018(2)
C24 0.069(2) 0.178(4) 0.111(3) -0.043(3) -0.034(2) 0.054(3)
C25 0.065(2) 0.099(3) 0.121(3) -0.034(2) 0.0158(19) 0.0256(19)
N1 0.0468(11) 0.0445(11) 0.0421(10) 0.0018(9) -0.0021(8) -0.0043(9)
N2 0.0734(17) 0.0489(14) 0.0664(16) -0.0037(11) 0.0240(13) -0.0100(12)
O1 0.1011(18) 0.0800(16) 0.0987(16) 0.0095(13) 0.0489(14) 0.0249(14)
O2 0.1010(17) 0.1060(18) 0.0585(13) -0.0148(13) 0.0131(12) -0.0051(14)
O3 0.0794(13) 0.0509(11) 0.0494(9) 0.0071(8) 0.0037(9) -0.0035(9)
O4 0.0434(10) 0.0904(14) 0.0706(11) -0.0172(10) 0.0093(9) -0.0171(10)
O5 0.0538(11) 0.0562(11) 0.0852(13) -0.0019(9) 0.0260(10) -0.0074(9)
O6 0.0512(11) 0.0883(14) 0.0612(11) 0.0083(10) 0.0144(9) -0.0142(10)
O7 0.0479(10) 0.0796(13) 0.0412(9) 0.0011(9) 0.0095(7) -0.0053(9)
O8 0.0640(11) 0.0422(10) 0.0711(11) -0.0063(8) 0.0170(9) 0.0016(9)
O9 0.0990(16) 0.0569(11) 0.0474(10) 0.0065(9) -0.0145(10) 0.0011(11)
S1 0.0448(3) 0.0490(4) 0.0495(3) -0.0028(3) 0.0048(3) -0.0086(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 121.0(2)
C6 C1 S1 120.83(19)
C2 C1 S1 118.07(18)
C3 C2 C1 119.3(2)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C3 C2 119.1(2)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 122.9(2)
C3 C4 N2 118.8(2)
C5 C4 N2 118.3(2)
C4 C5 C6 118.0(2)
C4 C5 H5 121.0
C6 C5 H5 121.0
C1 C6 C5 119.6(2)
C1 C6 H6 120.2
C5 C6 H6 120.2
O9 C7 C8 105.8(2)
O9 C7 H7A 110.6
C8 C7 H7A 110.6
O9 C7 H7B 110.6
C8 C7 H7B 110.6
H7A C7 H7B 108.7
C7 C8 C12 116.2(3)
C7 C8 C9 103.9(2)
C12 C8 C9 105.37(19)
C7 C8 H8 110.3
C12 C8 H8 110.3
C9 C8 H8 110.3
N1 C9 C10 110.81(17)
N1 C9 C8 106.00(18)
C10 C9 C8 107.09(19)
N1 C9 H9 110.9
C10 C9 H9 110.9
C8 C9 H9 110.9
C9 C10 C19 115.98(19)
C9 C10 C11 102.97(17)
C19 C10 C11 120.27(18)
C9 C10 H10 105.4
C19 C10 H10 105.4
C11 C10 H10 105.4
C13 C11 C16 108.41(18)
C13 C11 C12 110.83(19)
C16 C11 C12 110.38(18)
C13 C11 C10 113.07(18)
C16 C11 C10 112.62(18)
C12 C11 C10 101.42(17)
C8 C12 C11 105.80(19)
C8 C12 H12A 110.6
C11 C12 H12A 110.6
C8 C12 H12B 110.6
C11 C12 H12B 110.6
H12A C12 H12B 108.7
O5 C13 O8 124.1(2)
O5 C13 C11 126.2(2)
O8 C13 C11 109.69(19)
O8 C14 C15 108.2(3)
O8 C14 H14A 110.1
C15 C14 H14A 110.1
O8 C14 H14B 110.1
C15 C14 H14B 110.1
H14A C14 H14B 108.4
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O6 C16 O7 124.6(2)
O6 C16 C11 124.5(2)
O7 C16 C11 110.94(19)
O7 C17 C18 108.5(2)
O7 C17 H17A 110.0
C18 C17 H17A 110.0
O7 C17 H17B 110.0
C18 C17 H17B 110.0
H17A C17 H17B 108.4
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C20 C19 C10 114.8(2)
C20 C19 C21 110.0(2)
C10 C19 C21 110.50(18)
C20 C19 H19 107.1
C10 C19 H19 107.1
C21 C19 H19 107.1
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C22 C21 C19 119.0(2)
C22 C21 H21A 107.6
C19 C21 H21A 107.6
C22 C21 H21B 107.6
C19 C21 H21B 107.6
H21A C21 H21B 107.0
C24 C22 C21 112.1(3)
C24 C22 C23 110.4(3)
C21 C22 C23 108.6(2)
C24 C22 C25 109.7(3)
C21 C22 C25 107.9(2)
C23 C22 C25 107.9(3)
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C22 C24 H24A 109.5
C22 C24 H24B 109.5
H24A C24 H24B 109.5
C22 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C22 C25 H25A 109.5
C22 C25 H25B 109.5
H25A C25 H25B 109.5
C22 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
O9 N1 C9 106.35(16)
O9 N1 S1 108.86(13)
C9 N1 S1 115.64(14)
O1 N2 O2 124.2(3)
O1 N2 C4 117.8(3)
O2 N2 C4 117.9(3)
C16 O7 C17 118.14(19)
C13 O8 C14 117.4(2)
N1 O9 C7 106.67(19)
O4 S1 O3 119.29(11)
O4 S1 N1 113.68(11)
O3 S1 N1 104.36(10)
O4 S1 C1 108.50(11)
O3 S1 C1 108.96(11)
N1 S1 C1 100.35(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.378(3)
C1 C2 1.383(3)
C1 S1 1.767(2)
C2 C3 1.371(3)
C2 H2 0.9300
C3 C4 1.363(3)
C3 H3 0.9300
C4 C5 1.369(3)
C4 N2 1.480(3)
C5 C6 1.386(3)
C5 H5 0.9300
C6 H6 0.9300
C7 O9 1.459(4)
C7 C8 1.510(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C12 1.520(3)
C8 C9 1.544(3)
C8 H8 0.9800
C9 N1 1.491(3)
C9 C10 1.536(3)
C9 H9 0.9800
C10 C19 1.540(3)
C10 C11 1.560(3)
C10 H10 0.9800
C11 C13 1.522(3)
C11 C16 1.529(3)
C11 C12 1.540(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 O5 1.198(3)
C13 O8 1.327(3)
C14 O8 1.442(3)
C14 C15 1.486(4)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 O6 1.191(3)
C16 O7 1.329(3)
C17 O7 1.453(3)
C17 C18 1.462(4)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 C20 1.530(3)
C19 C21 1.546(3)
C19 H19 0.9800
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 C22 1.516(3)
C21 H21A 0.9700
C21 H21B 0.9700
C22 C24 1.509(4)
C22 C23 1.533(4)
C22 C25 1.534(4)
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
N1 O9 1.431(2)
N1 S1 1.6761(19)
N2 O1 1.211(3)
N2 O2 1.212(3)
O3 S1 1.4293(17)
O4 S1 1.4242(18)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -0.6(4)
S1 C1 C2 C3 -177.15(19)
C1 C2 C3 C4 -0.6(4)
C2 C3 C4 C5 0.9(4)
C2 C3 C4 N2 179.9(2)
C3 C4 C5 C6 0.0(4)
N2 C4 C5 C6 -179.0(2)
C2 C1 C6 C5 1.5(4)
S1 C1 C6 C5 178.0(2)
C4 C5 C6 C1 -1.2(4)
O9 C7 C8 C12 -94.3(3)
O9 C7 C8 C9 20.9(3)
C7 C8 C9 N1 -1.6(3)
C12 C8 C9 N1 121.0(2)
C7 C8 C9 C10 -120.0(2)
C12 C8 C9 C10 2.7(2)
N1 C9 C10 C19 84.7(2)
C8 C9 C10 C19 -160.16(19)
N1 C9 C10 C11 -141.90(17)
C8 C9 C10 C11 -26.7(2)
C9 C10 C11 C13 158.66(17)
C19 C10 C11 C13 -70.4(3)
C9 C10 C11 C16 -78.0(2)
C19 C10 C11 C16 52.9(3)
C9 C10 C11 C12 40.0(2)
C19 C10 C11 C12 170.87(19)
C7 C8 C12 C11 137.4(2)
C9 C8 C12 C11 23.1(2)
C13 C11 C12 C8 -159.61(19)
C16 C11 C12 C8 80.3(2)
C10 C11 C12 C8 -39.3(2)
C16 C11 C13 O5 -120.9(3)
C12 C11 C13 O5 117.9(3)
C10 C11 C13 O5 4.8(3)
C16 C11 C13 O8 59.4(2)
C12 C11 C13 O8 -61.9(2)
C10 C11 C13 O8 -175.01(17)
C13 C11 C16 O6 -149.0(2)
C12 C11 C16 O6 -27.4(3)
C10 C11 C16 O6 85.1(3)
C13 C11 C16 O7 32.2(3)
C12 C11 C16 O7 153.72(19)
C10 C11 C16 O7 -93.7(2)
C9 C10 C19 C20 50.3(3)
C11 C10 C19 C20 -74.7(3)
C9 C10 C19 C21 -74.8(2)
C11 C10 C19 C21 160.2(2)
C20 C19 C21 C22 103.9(3)
C10 C19 C21 C22 -128.4(2)
C19 C21 C22 C24 -55.7(4)
C19 C21 C22 C23 66.6(3)
C19 C21 C22 C25 -176.7(3)
C10 C9 N1 O9 97.2(2)
C8 C9 N1 O9 -18.7(2)
C10 C9 N1 S1 -141.84(16)
C8 C9 N1 S1 102.31(19)
C3 C4 N2 O1 -17.2(3)
C5 C4 N2 O1 161.9(3)
C3 C4 N2 O2 162.3(2)
C5 C4 N2 O2 -18.6(3)
O6 C16 O7 C17 6.0(4)
C11 C16 O7 C17 -175.1(2)
C18 C17 O7 C16 123.1(3)
O5 C13 O8 C14 6.9(4)
C11 C13 O8 C14 -173.4(2)
C15 C14 O8 C13 173.9(2)
C9 N1 O9 C7 32.7(2)
S1 N1 O9 C7 -92.5(2)
C8 C7 O9 N1 -33.8(3)
O9 N1 S1 O4 45.20(18)
C9 N1 S1 O4 -74.39(17)
O9 N1 S1 O3 176.79(14)
C9 N1 S1 O3 57.19(17)
O9 N1 S1 C1 -70.41(16)
C9 N1 S1 C1 170.00(15)
C6 C1 S1 O4 -15.0(2)
C2 C1 S1 O4 161.54(19)
C6 C1 S1 O3 -146.3(2)
C2 C1 S1 O3 30.2(2)
C6 C1 S1 N1 104.4(2)
C2 C1 S1 N1 -79.0(2)
|
1502020.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502020
loop_
_publ_author_name
'Kumar, Arepalli Sateesh'
'Nagarajan, Rajagopal'
_publ_section_title
;
Synthesis of \a-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack
reaction of 3-acetyl-2-chloroindoles.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1398
_journal_page_last 1401
_journal_paper_doi 10.1021/ol2000827
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C17 H17 Cl N2 O'
_chemical_formula_sum 'C17 H17 Cl N2 O'
_chemical_formula_weight 300.78
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 104.17(3)
_cell_angle_beta 103.50(3)
_cell_angle_gamma 96.70(3)
_cell_formula_units_Z 2
_cell_length_a 7.190(3)
_cell_length_b 10.650(4)
_cell_length_c 10.795(3)
_cell_measurement_reflns_used 1116
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 28.3447
_cell_measurement_theta_min 2.9679
_cell_volume 766.0(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0251
_diffrn_reflns_av_sigmaI/netI 0.0680
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 4859
_diffrn_reflns_theta_full 25.68
_diffrn_reflns_theta_max 25.68
_diffrn_reflns_theta_min 2.96
_exptl_absorpt_coefficient_mu 0.250
_exptl_absorpt_correction_T_max 0.9707
_exptl_absorpt_correction_T_min 0.9024
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_density_diffrn 1.304
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 316
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.12
_refine_diff_density_max 0.184
_refine_diff_density_min -0.158
_refine_diff_density_rms 0.031
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.841
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 229
_refine_ls_number_reflns 2900
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.841
_refine_ls_R_factor_all 0.1165
_refine_ls_R_factor_gt 0.0459
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0977
_refine_ls_wR_factor_ref 0.1145
_reflns_number_gt 1347
_reflns_number_total 2900
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000827_si_002.cif
_cod_data_source_block rn27
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_Hall '-P 1 '
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502020
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C13A C 0.7501(19) 0.0997(8) 0.6458(10) 0.092(4) Uani 0.537(15) 1 d P A 1
H13A H 0.6841 0.0145 0.6447 0.111 Uiso 0.537(15) 1 calc PR A 1
H13B H 0.7934 0.0894 0.5659 0.111 Uiso 0.537(15) 1 calc PR A 1
C14A C 0.9194(19) 0.1511(10) 0.7653(10) 0.103(4) Uani 0.537(15) 1 d P A 1
H14A H 0.8802 0.1432 0.8435 0.124 Uiso 0.537(15) 1 calc PR A 1
H14B H 0.9667 0.2435 0.7771 0.124 Uiso 0.537(15) 1 calc PR A 1
C15A C 1.097(3) 0.064(2) 0.746(3) 0.132(6) Uani 0.537(15) 1 d P A 1
H15A H 1.0779 0.0229 0.6533 0.198 Uiso 0.537(15) 1 calc PR A 1
H15B H 1.0929 -0.0016 0.7924 0.198 Uiso 0.537(15) 1 calc PR A 1
H15C H 1.2208 0.1227 0.7813 0.198 Uiso 0.537(15) 1 calc PR A 1
C13B C 0.8049(19) 0.1572(13) 0.7308(13) 0.094(3) Uani 0.463(15) 1 d P A 2
H13C H 0.8943 0.2366 0.7877 0.113 Uiso 0.463(15) 1 calc PR A 2
H13D H 0.7689 0.1055 0.7870 0.113 Uiso 0.463(15) 1 calc PR A 2
C14B C 0.901(2) 0.0826(9) 0.6432(12) 0.108(4) Uani 0.463(15) 1 d P A 2
H14C H 0.9620 0.1370 0.5983 0.129 Uiso 0.463(15) 1 calc PR A 2
H14D H 0.8114 0.0079 0.5777 0.129 Uiso 0.463(15) 1 calc PR A 2
C15B C 1.058(5) 0.037(4) 0.744(4) 0.228(18) Uani 0.463(15) 1 d P A 2
H15D H 0.9980 0.0044 0.8034 0.343 Uiso 0.463(15) 1 calc PR A 2
H15E H 1.1613 0.1098 0.7936 0.343 Uiso 0.463(15) 1 calc PR A 2
H15F H 1.1101 -0.0324 0.6952 0.343 Uiso 0.463(15) 1 calc PR A 2
H12A H 0.565(4) 0.227(3) 0.725(3) 0.092(10) Uiso 1 1 d . . .
H12B H 0.507(5) 0.143(3) 0.582(3) 0.138(15) Uiso 1 1 d . . .
Cl1 Cl 0.79066(9) 0.62581(8) 0.35799(8) 0.0923(3) Uani 1 1 d . . .
N1 N 0.5965(3) 0.2152(2) 0.3825(2) 0.0661(6) Uani 1 1 d . . .
C11 C 0.6603(3) 0.3204(3) 0.4874(3) 0.0541(6) Uani 1 1 d . . .
N2 N 0.6724(2) 0.3148(2) 0.61418(19) 0.0594(6) Uani 1 1 d . A .
C4 C 0.7242(3) 0.4496(2) 0.4872(2) 0.0513(6) Uani 1 1 d . . .
C5 C 0.7795(3) 0.5267(3) 0.6241(2) 0.0538(6) Uani 1 1 d . . .
C10 C 0.7444(3) 0.4399(3) 0.6981(2) 0.0578(7) Uani 1 1 d . . .
C3 C 0.7156(3) 0.4683(3) 0.3643(3) 0.0616(7) Uani 1 1 d . . .
C2 C 0.6474(3) 0.3619(3) 0.2500(2) 0.0666(8) Uani 1 1 d . . .
C1 C 0.5912(3) 0.2373(3) 0.2654(3) 0.0690(8) Uani 1 1 d . . .
C9 C 0.7786(4) 0.4816(3) 0.8348(3) 0.0787(8) Uani 1 1 d . . .
H9 H 0.7531 0.4232 0.8827 0.094 Uiso 1 1 calc R . .
O1 O 0.5860(4) 0.3032(3) 0.0143(2) 0.1359(10) Uani 1 1 d . . .
C6 C 0.8531(3) 0.6589(3) 0.6896(3) 0.0751(8) Uani 1 1 d . . .
H6 H 0.8775 0.7187 0.6428 0.090 Uiso 1 1 calc R . .
C12 C 0.6151(5) 0.1965(4) 0.6516(4) 0.0854(10) Uani 1 1 d . . .
C8 C 0.8511(4) 0.6117(4) 0.8958(3) 0.0946(10) Uani 1 1 d . . .
H8 H 0.8759 0.6425 0.9876 0.114 Uiso 1 1 calc R . .
C16 C 0.5193(4) 0.1173(3) 0.1483(3) 0.1058(11) Uani 1 1 d . . .
H16A H 0.4939 0.0411 0.1786 0.159 Uiso 1 1 calc R . .
H16B H 0.6164 0.1066 0.1008 0.159 Uiso 1 1 calc R . .
H16C H 0.4017 0.1274 0.0907 0.159 Uiso 1 1 calc R . .
C17 C 0.6384(4) 0.3850(4) 0.1187(3) 0.0995(11) Uani 1 1 d . . .
H17 H 0.6774 0.4712 0.1181 0.119 Uiso 1 1 calc R . .
C7 C 0.8889(4) 0.6992(3) 0.8254(4) 0.0949(10) Uani 1 1 d . . .
H7 H 0.9397 0.7873 0.8708 0.114 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C13A 0.115(9) 0.079(5) 0.067(5) 0.020(5) 0.007(5) -0.011(5)
C14A 0.119(8) 0.100(6) 0.069(6) 0.026(5) -0.008(6) -0.007(7)
C15A 0.090(6) 0.099(8) 0.214(19) 0.068(10) 0.015(9) 0.046(7)
C13B 0.095(8) 0.094(7) 0.075(7) 0.035(6) -0.016(7) 0.000(7)
C14B 0.082(8) 0.108(7) 0.122(10) 0.018(6) 0.027(6) 0.012(5)
C15B 0.19(3) 0.16(2) 0.27(3) 0.04(2) -0.072(19) 0.051(17)
Cl1 0.0773(5) 0.1083(7) 0.1198(7) 0.0679(6) 0.0403(4) 0.0236(4)
N1 0.0610(12) 0.0792(16) 0.0533(14) 0.0130(14) 0.0130(11) 0.0121(12)
C11 0.0428(12) 0.0718(19) 0.0484(16) 0.0198(16) 0.0103(11) 0.0106(13)
N2 0.0568(12) 0.0737(16) 0.0500(14) 0.0250(13) 0.0127(10) 0.0079(11)
C4 0.0368(12) 0.0693(18) 0.0520(16) 0.0217(15) 0.0135(11) 0.0137(12)
C5 0.0355(12) 0.0617(17) 0.0590(16) 0.0105(16) 0.0089(12) 0.0105(12)
C10 0.0454(13) 0.079(2) 0.0474(16) 0.0166(17) 0.0094(12) 0.0161(13)
C3 0.0433(13) 0.086(2) 0.0726(19) 0.0421(18) 0.0239(13) 0.0213(13)
C2 0.0543(15) 0.108(2) 0.0460(17) 0.0240(18) 0.0214(13) 0.0261(16)
C1 0.0572(15) 0.095(2) 0.0507(18) 0.0108(18) 0.0119(13) 0.0238(15)
C9 0.0705(17) 0.109(3) 0.0534(19) 0.0161(19) 0.0113(15) 0.0282(18)
O1 0.1362(19) 0.218(3) 0.0563(14) 0.0369(18) 0.0341(14) 0.0315(19)
C6 0.0544(15) 0.081(2) 0.084(2) 0.0192(19) 0.0104(15) 0.0152(15)
C12 0.082(2) 0.106(3) 0.088(3) 0.053(2) 0.033(2) 0.020(2)
C8 0.077(2) 0.130(3) 0.0570(19) -0.001(2) -0.0004(16) 0.036(2)
C16 0.113(2) 0.118(3) 0.063(2) -0.008(2) 0.0106(18) 0.029(2)
C17 0.092(2) 0.158(3) 0.066(2) 0.046(2) 0.0341(19) 0.036(2)
C7 0.0662(18) 0.093(3) 0.094(3) -0.008(2) -0.0023(19) 0.0163(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14A C13A C12 107.8(9)
C14A C13A H13A 110.1
C12 C13A H13A 110.1
C14A C13A H13B 110.1
C12 C13A H13B 110.1
H13A C13A H13B 108.5
C13A C14A C15A 109.2(14)
C13A C14A H14A 109.8
C15A C14A H14A 109.8
C13A C14A H14B 109.8
C15A C14A H14B 109.8
H14A C14A H14B 108.3
C14B C13B C12 112.1(12)
C14B C13B H13C 109.2
C12 C13B H13C 109.2
C14B C13B H13D 109.2
C12 C13B H13D 109.2
H13C C13B H13D 107.9
C13B C14B C15B 101.7(18)
C13B C14B H14C 111.4
C15B C14B H14C 111.4
C13B C14B H14D 111.4
C15B C14B H14D 111.4
H14C C14B H14D 109.3
C14B C15B H15D 109.5
C14B C15B H15E 109.5
H15D C15B H15E 109.5
C14B C15B H15F 109.5
H15D C15B H15F 109.5
H15E C15B H15F 109.5
C11 N1 C1 115.6(2)
N1 C11 N2 122.9(2)
N1 C11 C4 126.8(2)
N2 C11 C4 110.3(2)
C11 N2 C10 107.9(2)
C11 N2 C12 125.3(3)
C10 N2 C12 126.7(2)
C3 C4 C11 115.8(2)
C3 C4 C5 138.5(3)
C11 C4 C5 105.7(2)
C6 C5 C10 119.1(3)
C6 C5 C4 134.4(3)
C10 C5 C4 106.5(2)
N2 C10 C9 128.3(3)
N2 C10 C5 109.5(2)
C9 C10 C5 122.2(3)
C4 C3 C2 120.2(2)
C4 C3 Cl1 117.8(2)
C2 C3 Cl1 122.1(2)
C3 C2 C1 117.9(2)
C3 C2 C17 119.1(3)
C1 C2 C17 123.1(3)
N1 C1 C2 123.8(3)
N1 C1 C16 114.8(3)
C2 C1 C16 121.5(3)
C8 C9 C10 117.2(3)
C8 C9 H9 121.4
C10 C9 H9 121.4
C7 C6 C5 118.4(3)
C7 C6 H6 120.8
C5 C6 H6 120.8
N2 C12 C13A 115.9(4)
N2 C12 C13B 108.9(5)
C13A C12 C13B 35.0(5)
N2 C12 H12A 104.1(18)
C13A C12 H12A 124.3(17)
C13B C12 H12A 97.2(16)
N2 C12 H12B 107(2)
C13A C12 H12B 98(2)
C13B C12 H12B 130(2)
H12A C12 H12B 106(3)
C9 C8 C7 121.8(3)
C9 C8 H8 119.1
C7 C8 H8 119.1
C1 C16 H16A 109.5
C1 C16 H16B 109.5
H16A C16 H16B 109.5
C1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O1 C17 C2 125.9(4)
O1 C17 H17 117.0
C2 C17 H17 117.0
C6 C7 C8 121.4(3)
C6 C7 H7 119.3
C8 C7 H7 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C13A C14A 1.487(18)
C13A C12 1.496(12)
C13A H13A 0.9700
C13A H13B 0.9700
C14A C15A 1.68(2)
C14A H14A 0.9700
C14A H14B 0.9700
C15A H15A 0.9600
C15A H15B 0.9600
C15A H15C 0.9600
C13B C14B 1.44(2)
C13B C12 1.591(12)
C13B H13C 0.9700
C13B H13D 0.9700
C14B C15B 1.58(4)
C14B H14C 0.9700
C14B H14D 0.9700
C15B H15D 0.9600
C15B H15E 0.9600
C15B H15F 0.9600
Cl1 C3 1.724(3)
N1 C11 1.329(3)
N1 C1 1.335(3)
C11 N2 1.367(3)
C11 C4 1.399(3)
N2 C10 1.375(3)
N2 C12 1.459(4)
C4 C3 1.377(3)
C4 C5 1.440(3)
C5 C6 1.387(4)
C5 C10 1.400(3)
C10 C9 1.386(3)
C3 C2 1.397(3)
C2 C1 1.402(4)
C2 C17 1.485(4)
C1 C16 1.499(4)
C9 C8 1.360(4)
C9 H9 0.9300
O1 C17 1.190(4)
C6 C7 1.374(4)
C6 H6 0.9300
C12 H12A 0.95(3)
C12 H12B 0.95(3)
C8 C7 1.380(4)
C8 H8 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17 0.9300
C7 H7 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 C13A C14A C15A -167.3(11)
C12 C13B C14B C15B -170.8(16)
C1 N1 C11 N2 179.2(2)
C1 N1 C11 C4 -1.1(3)
N1 C11 N2 C10 179.7(2)
C4 C11 N2 C10 -0.1(2)
N1 C11 N2 C12 -1.3(4)
C4 C11 N2 C12 179.0(2)
N1 C11 C4 C3 1.4(3)
N2 C11 C4 C3 -178.86(17)
N1 C11 C4 C5 -179.4(2)
N2 C11 C4 C5 0.3(2)
C3 C4 C5 C6 -1.1(5)
C11 C4 C5 C6 -180.0(2)
C3 C4 C5 C10 178.5(2)
C11 C4 C5 C10 -0.4(2)
C11 N2 C10 C9 179.0(2)
C12 N2 C10 C9 0.0(4)
C11 N2 C10 C5 -0.2(2)
C12 N2 C10 C5 -179.2(2)
C6 C5 C10 N2 -179.98(18)
C4 C5 C10 N2 0.4(2)
C6 C5 C10 C9 0.7(3)
C4 C5 C10 C9 -178.9(2)
C11 C4 C3 C2 -0.4(3)
C5 C4 C3 C2 -179.2(2)
C11 C4 C3 Cl1 179.48(15)
C5 C4 C3 Cl1 0.7(4)
C4 C3 C2 C1 -0.7(3)
Cl1 C3 C2 C1 179.46(17)
C4 C3 C2 C17 179.6(2)
Cl1 C3 C2 C17 -0.2(3)
C11 N1 C1 C2 -0.1(3)
C11 N1 C1 C16 179.8(2)
C3 C2 C1 N1 1.0(4)
C17 C2 C1 N1 -179.3(2)
C3 C2 C1 C16 -179.0(2)
C17 C2 C1 C16 0.7(4)
N2 C10 C9 C8 180.0(2)
C5 C10 C9 C8 -0.9(4)
C10 C5 C6 C7 0.1(3)
C4 C5 C6 C7 179.6(2)
C11 N2 C12 C13A 74.4(6)
C10 N2 C12 C13A -106.7(6)
C11 N2 C12 C13B 111.7(6)
C10 N2 C12 C13B -69.5(7)
C14A C13A C12 N2 77.5(8)
C14A C13A C12 C13B -8.7(10)
C14B C13B C12 N2 -83.0(10)
C14B C13B C12 C13A 25.5(8)
C10 C9 C8 C7 0.2(4)
C3 C2 C17 O1 179.0(3)
C1 C2 C17 O1 -0.7(5)
C5 C6 C7 C8 -0.8(4)
C9 C8 C7 C6 0.6(4)
|
1502021.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502021.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502021
loop_
_publ_author_name
'Kumar, Arepalli Sateesh'
'Nagarajan, Rajagopal'
_publ_section_title
;
Synthesis of \a-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack
reaction of 3-acetyl-2-chloroindoles.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1398
_journal_page_last 1401
_journal_paper_doi 10.1021/ol2000827
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C14 H16 N2 O2'
_chemical_formula_sum 'C14 H16 N2 O2'
_chemical_formula_weight 244.29
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.466(5)
_cell_length_b 9.680(3)
_cell_length_c 16.183(7)
_cell_measurement_reflns_used 644
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 23.1957
_cell_measurement_theta_min 3.2048
_cell_volume 1326.2(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0592
_diffrn_reflns_av_sigmaI/netI 0.1327
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 2871
_diffrn_reflns_theta_full 23.52
_diffrn_reflns_theta_max 23.52
_diffrn_reflns_theta_min 3.20
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_T_max 0.9917
_exptl_absorpt_correction_T_min 0.9755
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.223
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 520
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.143
_refine_diff_density_min -0.137
_refine_diff_density_rms 0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -1(3)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.829
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 170
_refine_ls_number_reflns 1784
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.829
_refine_ls_R_factor_all 0.1142
_refine_ls_R_factor_gt 0.0514
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0881
_refine_ls_wR_factor_ref 0.1021
_reflns_number_gt 918
_reflns_number_total 1784
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2000827_si_003.cif
_cod_data_source_block satish35
_cod_original_cell_volume 1326.2(10)
_cod_original_sg_symbol_Hall 'P 2ac 2ab '
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1502021
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N3 N 0.0766(4) 0.1433(3) 0.5300(2) 0.0432(10) Uani 1 1 d .
C8 C -0.0744(5) 0.0115(4) 0.6159(3) 0.0396(11) Uani 1 1 d .
N2 N 0.1119(5) -0.0041(4) 0.4113(2) 0.0513(11) Uani 1 1 d .
C1 C 0.0423(5) 0.0207(4) 0.4895(3) 0.0421(12) Uani 1 1 d .
C3 C 0.0053(5) 0.1386(4) 0.6080(3) 0.0416(12) Uani 1 1 d .
C15 C -0.0490(5) -0.0624(4) 0.5394(3) 0.0395(12) Uani 1 1 d .
C7 C -0.1575(5) -0.0161(4) 0.6884(3) 0.0517(13) Uani 1 1 d .
H7 H -0.2136 -0.0980 0.6946 0.062 Uiso 1 1 calc R
C11 C 0.1620(5) 0.2635(4) 0.4979(3) 0.0541(13) Uani 1 1 d .
H11A H 0.2205 0.2363 0.4489 0.065 Uiso 1 1 calc R
H11B H 0.2376 0.2942 0.5390 0.065 Uiso 1 1 calc R
C9 C -0.1175(6) -0.1987(4) 0.5215(3) 0.0524(14) Uani 1 1 d .
C14 C 0.1303(6) -0.0076(5) 0.2622(3) 0.0816(18) Uani 1 1 d .
H14A H 0.0815 -0.0934 0.2471 0.122 Uiso 1 1 calc R
H14B H 0.2405 -0.0226 0.2729 0.122 Uiso 1 1 calc R
H14C H 0.1187 0.0576 0.2179 0.122 Uiso 1 1 calc R
C13 C 0.0517(7) 0.0487(5) 0.3393(3) 0.0565(13) Uani 1 1 d .
C12 C 0.0519(6) 0.3842(3) 0.4758(3) 0.0669(15) Uani 1 1 d .
H12A H -0.0195 0.3560 0.4329 0.100 Uiso 1 1 calc R
H12B H 0.1137 0.4611 0.4568 0.100 Uiso 1 1 calc R
H12C H -0.0072 0.4110 0.5238 0.100 Uiso 1 1 calc R
C5 C -0.0719(6) 0.2058(5) 0.7427(3) 0.0639(14) Uani 1 1 d .
H5 H -0.0704 0.2684 0.7863 0.077 Uiso 1 1 calc R
C10 C -0.1037(7) -0.2607(4) 0.4355(3) 0.0745(16) Uani 1 1 d .
H10A H 0.0045 -0.2841 0.4247 0.112 Uiso 1 1 calc R
H10B H -0.1393 -0.1947 0.3953 0.112 Uiso 1 1 calc R
H10C H -0.1677 -0.3424 0.4321 0.112 Uiso 1 1 calc R
C4 C 0.0073(6) 0.2366(4) 0.6711(3) 0.0566(13) Uani 1 1 d .
H4 H 0.0604 0.3201 0.6648 0.068 Uiso 1 1 calc R
C6 C -0.1546(6) 0.0821(5) 0.7512(3) 0.0664(16) Uani 1 1 d .
H6 H -0.2091 0.0647 0.8000 0.080 Uiso 1 1 calc R
O1 O -0.0523(5) 0.1338(3) 0.3382(2) 0.0804(12) Uani 1 1 d .
O2 O -0.1877(4) -0.2617(3) 0.5749(2) 0.0792(12) Uani 1 1 d .
H1B H 0.156(6) -0.086(4) 0.410(3) 0.084(19) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N3 0.042(2) 0.035(2) 0.053(3) 0.008(2) 0.005(2) -0.003(2)
C8 0.041(3) 0.034(2) 0.044(3) 0.003(2) 0.001(3) 0.002(3)
N2 0.064(3) 0.038(2) 0.052(3) 0.005(2) 0.006(3) 0.011(2)
C1 0.051(3) 0.026(2) 0.049(3) 0.000(2) -0.007(3) 0.012(3)
C3 0.043(3) 0.033(3) 0.049(3) -0.002(3) -0.006(3) 0.000(2)
C15 0.046(3) 0.025(2) 0.047(3) 0.008(2) -0.003(3) -0.004(2)
C7 0.063(4) 0.043(3) 0.049(3) 0.003(3) 0.003(3) 0.003(3)
C11 0.050(3) 0.042(2) 0.070(3) 0.004(3) 0.009(3) -0.006(3)
C9 0.062(4) 0.041(3) 0.054(4) 0.005(3) -0.011(3) -0.003(3)
C14 0.108(5) 0.083(3) 0.054(3) 0.001(3) 0.010(4) -0.003(4)
C13 0.069(4) 0.052(3) 0.048(4) 0.008(3) -0.002(3) -0.003(3)
C12 0.063(4) 0.037(2) 0.101(4) 0.015(3) 0.012(3) 0.002(3)
C5 0.077(4) 0.054(3) 0.061(4) -0.011(3) 0.005(4) 0.007(3)
C10 0.104(4) 0.044(3) 0.075(4) -0.013(3) -0.016(4) -0.016(3)
C4 0.065(4) 0.047(3) 0.059(3) -0.007(3) -0.003(3) -0.002(3)
C6 0.079(4) 0.066(3) 0.054(4) 0.003(3) 0.016(3) 0.011(3)
O1 0.094(3) 0.076(2) 0.071(2) 0.006(2) -0.020(3) 0.036(3)
O2 0.116(3) 0.062(2) 0.060(3) 0.0066(19) 0.010(3) -0.035(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N3 C3 107.9(3)
C1 N3 C11 128.0(4)
C3 N3 C11 123.9(4)
C7 C8 C3 119.1(4)
C7 C8 C15 134.5(4)
C3 C8 C15 106.4(4)
C13 N2 C1 122.8(4)
C13 N2 H1B 119(3)
C1 N2 H1B 110(3)
C15 C1 N3 109.9(4)
C15 C1 N2 131.1(4)
N3 C1 N2 118.7(4)
C4 C3 N3 129.3(4)
C4 C3 C8 122.3(4)
N3 C3 C8 108.5(4)
C1 C15 C8 107.2(3)
C1 C15 C9 129.1(4)
C8 C15 C9 123.7(4)
C6 C7 C8 118.4(4)
C6 C7 H7 120.8
C8 C7 H7 120.8
N3 C11 C12 112.8(3)
N3 C11 H11A 109.0
C12 C11 H11A 109.0
N3 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
O2 C9 C15 120.2(4)
O2 C9 C10 119.5(4)
C15 C9 C10 120.3(4)
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O1 C13 N2 122.5(5)
O1 C13 C14 123.7(5)
N2 C13 C14 113.7(5)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C4 C5 C6 121.1(4)
C4 C5 H5 119.5
C6 C5 H5 119.5
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C5 C4 C3 117.7(4)
C5 C4 H4 121.2
C3 C4 H4 121.2
C7 C6 C5 121.5(5)
C7 C6 H6 119.2
C5 C6 H6 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C1 1.386(5)
N3 C3 1.400(5)
N3 C11 1.465(5)
C8 C7 1.393(5)
C8 C3 1.409(5)
C8 C15 1.447(5)
N2 C13 1.371(5)
N2 C1 1.416(5)
N2 H1B 0.88(4)
C1 C15 1.378(5)
C3 C4 1.394(5)
C15 C9 1.470(5)
C7 C6 1.392(5)
C7 H7 0.9300
C11 C12 1.537(5)
C11 H11A 0.9700
C11 H11B 0.9700
C9 O2 1.214(5)
C9 C10 1.520(5)
C14 C13 1.514(6)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C13 O1 1.206(5)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C5 C4 1.373(6)
C5 C6 1.394(6)
C5 H5 0.9300
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C4 H4 0.9300
C6 H6 0.9300
|
1502022.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502022.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502022
loop_
_publ_author_name
'Breuning, M Andr\'e'
'Harms, Klaus'
'Koert, Ulrich'
_publ_section_title
;
The imidato-alkenyllithium route for the synthesis of the
isoquinocycline-pyrrolopyrrole substructure.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1402
_journal_page_last 1405
_journal_paper_doi 10.1021/ol200085g
_journal_volume 13
_journal_year 2011
_chemical_compound_source 'synthesis as described'
_chemical_formula_moiety 'C31 H40 N2 O5 S Si, 0.5(C4 H8 O2)'
_chemical_formula_sum 'C33 H44 N2 O6 S Si'
_chemical_formula_weight 624.85
_chemical_name_systematic ?
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_Int_Tables_number 2
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_date 2011-01-11T14:22:40-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 79.724(6)
_cell_angle_beta 89.131(6)
_cell_angle_gamma 71.349(5)
_cell_formula_units_Z 2
_cell_length_a 10.6719(7)
_cell_length_b 12.0517(8)
_cell_length_c 13.6594(10)
_cell_measurement_reflns_used 16455
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 25
_cell_measurement_theta_min 4.5
_cell_measurement_wavelength 0.71073
_cell_volume 1636.2(2)
_computing_cell_refinement 'STOE X-AREA'
_computing_data_collection 'STOE X-AREA'
_computing_data_reduction 'STOE X-AREA'
_computing_molecular_graphics 'DIAMOND 3.2'
_computing_publication_material 'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'STOE IPDS 2T'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0423
_diffrn_reflns_av_unetI/netI 0.0376
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 16685
_diffrn_reflns_theta_full 25
_diffrn_reflns_theta_max 25
_diffrn_reflns_theta_min 4.64
_exptl_absorpt_coefficient_mu 0.181
_exptl_absorpt_correction_T_max 1.0003
_exptl_absorpt_correction_T_min 0.9089
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'c.f. R.H. Blessing, Acta Cryst. (1995), A51, 33-38'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.268
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 668
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.3
_exptl_crystal_size_min 0.16
_refine_diff_density_max 0.301
_refine_diff_density_min -0.328
_refine_diff_density_rms 0.041
_refine_ls_extinction_coef 0.0068(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment noref
_refine_ls_matrix_type full
_refine_ls_number_parameters 420
_refine_ls_number_reflns 5729
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.044
_refine_ls_R_factor_all 0.0433
_refine_ls_R_factor_gt 0.0336
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0865
_refine_ls_wR_factor_ref 0.0893
_reflns_number_gt 4707
_reflns_number_total 5729
_reflns_threshold_expression >2\s(I)
_cod_data_source_file ol200085g_si_002.cif
_cod_data_source_block mab1014
_cod_original_cell_volume 1636.19(19)
_cod_database_code 1502022
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85027(15) 0.30573(13) 0.46079(11) 0.0210(3) Uani 1 1 d . . .
C2 C 0.72435(15) 0.31825(13) 0.51986(11) 0.0206(3) Uani 1 1 d . . .
H2 H 0.6972 0.3958 0.5439 0.025 Uiso 1 1 calc R . .
C3 C 0.61114(15) 0.31123(13) 0.45843(11) 0.0208(3) Uani 1 1 d . . .
C4 C 0.48173(16) 0.35020(14) 0.48975(12) 0.0251(4) Uani 1 1 d . . .
H4 H 0.4644 0.3826 0.549 0.03 Uiso 1 1 calc R . .
C5 C 0.37896(16) 0.34163(15) 0.43453(13) 0.0277(4) Uani 1 1 d . . .
H5 H 0.2912 0.3677 0.4564 0.033 Uiso 1 1 calc R . .
C6 C 0.40232(16) 0.29552(14) 0.34760(13) 0.0265(4) Uani 1 1 d . . .
H6 H 0.3311 0.2893 0.3104 0.032 Uiso 1 1 calc R . .
C7 C 0.53064(16) 0.25839(13) 0.31503(12) 0.0229(3) Uani 1 1 d . . .
C8 C 0.63648(15) 0.26547(13) 0.37078(12) 0.0203(3) Uani 1 1 d . . .
C9 C 0.77450(15) 0.23736(13) 0.33145(11) 0.0206(3) Uani 1 1 d . . .
H9 H 0.79 0.1823 0.2825 0.025 Uiso 1 1 calc R . .
C10 C 0.88076(15) 0.19416(14) 0.41587(12) 0.0220(3) Uani 1 1 d . . .
H10A H 0.8702 0.1263 0.4642 0.026 Uiso 1 1 calc R . .
H10B H 0.9711 0.1714 0.3904 0.026 Uiso 1 1 calc R . .
C11 C 0.79403(15) 0.35870(13) 0.28690(11) 0.0198(3) Uani 1 1 d . . .
C12 C 0.67680(15) 0.45042(13) 0.22851(11) 0.0201(3) Uani 1 1 d . . .
H12 H 0.6045 0.491 0.2641 0.024 Uiso 1 1 calc R . .
C13 C 0.66893(15) 0.47791(14) 0.12925(12) 0.0220(3) Uani 1 1 d . . .
C14 C 0.77314(16) 0.41707(15) 0.06340(12) 0.0261(4) Uani 1 1 d . . .
H14A H 0.8147 0.4745 0.028 0.031 Uiso 1 1 calc R . .
H14B H 0.7317 0.3884 0.013 0.031 Uiso 1 1 calc R . .
C15 C 0.87811(16) 0.31252(15) 0.12572(12) 0.0247(3) Uani 1 1 d . . .
H15A H 0.8461 0.2429 0.1377 0.03 Uiso 1 1 calc R . .
H15B H 0.9592 0.2915 0.0874 0.03 Uiso 1 1 calc R . .
C16 C 0.95904(16) 0.32087(15) 0.52131(12) 0.0264(4) Uani 1 1 d . . .
H16A H 0.9291 0.3999 0.5397 0.04 Uiso 1 1 calc R . .
H16B H 1.0378 0.3129 0.4817 0.04 Uiso 1 1 calc R . .
H16C H 0.9809 0.2596 0.5818 0.04 Uiso 1 1 calc R . .
C18 C 0.55595(17) 0.57286(15) 0.08050(12) 0.0252(4) Uani 1 1 d . . .
C19 C 0.45573(19) 0.21133(17) 0.16900(14) 0.0348(4) Uani 1 1 d . . .
H19A H 0.39 0.2909 0.1526 0.052 Uiso 1 1 calc R . .
H19B H 0.4144 0.156 0.2064 0.052 Uiso 1 1 calc R . .
H19C H 0.4896 0.1839 0.1075 0.052 Uiso 1 1 calc R . .
C20 C 0.75130(19) 0.35989(16) 0.75646(13) 0.0318(4) Uani 1 1 d . . .
H20A H 0.6892 0.4318 0.7168 0.048 Uiso 1 1 calc R . .
H20B H 0.8422 0.3585 0.7432 0.048 Uiso 1 1 calc R . .
H20C H 0.736 0.3599 0.8274 0.048 Uiso 1 1 calc R . .
C21 C 0.55388(16) 0.22379(15) 0.74594(13) 0.0278(4) Uani 1 1 d . . .
H21A H 0.536 0.1648 0.7122 0.042 Uiso 1 1 calc R . .
H21B H 0.4907 0.3028 0.7203 0.042 Uiso 1 1 calc R . .
H21C H 0.5446 0.2028 0.8177 0.042 Uiso 1 1 calc R . .
C22 C 0.84576(17) 0.08364(15) 0.79357(13) 0.0291(4) Uani 1 1 d . . .
C23 C 0.8034(2) -0.02289(17) 0.78188(19) 0.0505(6) Uani 1 1 d . . .
H23A H 0.8687 -0.0963 0.8168 0.076 Uiso 1 1 calc R . .
H23B H 0.7976 -0.0264 0.711 0.076 Uiso 1 1 calc R . .
H23C H 0.7167 -0.0144 0.8104 0.076 Uiso 1 1 calc R . .
C24 C 0.8469(2) 0.0929(2) 0.90436(15) 0.0542(6) Uani 1 1 d . . .
H24A H 0.8988 0.0158 0.9436 0.081 Uiso 1 1 calc R . .
H24B H 0.7559 0.1155 0.9266 0.081 Uiso 1 1 calc R . .
H24C H 0.8867 0.1535 0.9135 0.081 Uiso 1 1 calc R . .
C25 C 0.98604(19) 0.06354(18) 0.75707(17) 0.0435(5) Uani 1 1 d . . .
H25A H 0.9877 0.053 0.6875 0.065 Uiso 1 1 calc R . .
H25B H 1.047 -0.0079 0.7982 0.065 Uiso 1 1 calc R . .
H25C H 1.0134 0.1327 0.7621 0.065 Uiso 1 1 calc R . .
C26 C 0.92477(16) 0.56737(14) 0.19639(12) 0.0238(3) Uani 1 1 d . . .
C27 C 0.90648(17) 0.62800(15) 0.09823(13) 0.0284(4) Uani 1 1 d . . .
H27 H 0.9475 0.5887 0.046 0.034 Uiso 1 1 calc R . .
C28 C 0.82805(18) 0.74597(16) 0.07771(14) 0.0339(4) Uani 1 1 d . . .
H28 H 0.8147 0.7874 0.0107 0.041 Uiso 1 1 calc R . .
C29 C 0.76821(18) 0.80545(16) 0.15316(14) 0.0334(4) Uani 1 1 d . . .
C30 C 0.79089(18) 0.74364(16) 0.25107(14) 0.0321(4) Uani 1 1 d . . .
H30 H 0.7524 0.7836 0.3035 0.039 Uiso 1 1 calc R . .
C31 C 0.86827(17) 0.62540(15) 0.27328(13) 0.0265(4) Uani 1 1 d . . .
H31 H 0.8827 0.5842 0.3403 0.032 Uiso 1 1 calc R . .
C32 C 0.6814(2) 0.93388(17) 0.13015(18) 0.0476(5) Uani 1 1 d . . .
H32A H 0.6482 0.9604 0.1922 0.071 Uiso 0.5 1 calc PR . .
H32B H 0.6066 0.9417 0.0857 0.071 Uiso 0.5 1 calc PR . .
H32C H 0.7331 0.9831 0.0976 0.071 Uiso 0.5 1 calc PR . .
H32D H 0.6771 0.9631 0.0582 0.071 Uiso 0.5 1 calc PR . .
H32E H 0.7186 0.9817 0.1646 0.071 Uiso 0.5 1 calc PR . .
H32F H 0.5922 0.9404 0.1527 0.071 Uiso 0.5 1 calc PR . .
N1 N 0.91240(12) 0.33640(11) 0.22310(10) 0.0215(3) Uani 1 1 d . . .
N2 N 0.46790(15) 0.64956(13) 0.04069(11) 0.0330(3) Uani 1 1 d . . .
O1 O 0.81587(10) 0.40245(9) 0.37284(7) 0.0200(2) Uani 1 1 d . . .
O2 O 0.75717(11) 0.22174(9) 0.60373(8) 0.0223(2) Uani 1 1 d . . .
O3 O 0.56265(11) 0.21600(10) 0.22828(8) 0.0275(3) Uani 1 1 d . . .
O4 O 1.07890(11) 0.38687(11) 0.31837(8) 0.0297(3) Uani 1 1 d . . .
O5 O 1.09711(11) 0.38682(11) 0.13825(9) 0.0300(3) Uani 1 1 d . . .
Si1 Si 0.72553(4) 0.22581(4) 0.72216(3) 0.02091(12) Uani 1 1 d . . .
S2 S 1.01643(4) 0.41377(4) 0.22162(3) 0.02344(12) Uani 1 1 d . . .
O100 O 0.5896(5) 0.9498(4) 0.3756(4) 0.1033(15) Uani 0.5 1 d P A -1
O101 O 0.5 1 0.5 0.0619(7) Uani 1 2 d S . .
C101 C 0.7382(9) 0.9446(7) 0.5046(5) 0.0559(19) Uani 0.5 1 d P A -1
H10C H 0.8067 0.9167 0.46 0.084 Uiso 0.5 1 d PR A -1
H10D H 0.7517 0.8866 0.5649 0.084 Uiso 0.5 1 d PR A -1
H10E H 0.7409 1.0185 0.5198 0.084 Uiso 0.5 1 d PR A -1
C102 C 0.6090(4) 0.9625(3) 0.4554(3) 0.0364(9) Uani 0.5 1 d P A -1
C103 C 0.3729(4) 1.0124(3) 0.4739(3) 0.0313(8) Uani 0.5 1 d P A -1
H10F H 0.3697 0.9357 0.466 0.038 Uiso 0.5 1 d PR A -1
H10J H 0.3508 1.0638 0.4099 0.038 Uiso 0.5 1 d PR A -1
C104 C 0.2669(8) 1.0606(6) 0.5433(5) 0.0465(16) Uani 0.5 1 d P A -1
H10G H 0.182 1.0653 0.5171 0.07 Uiso 0.5 1 d PR A -1
H10H H 0.2662 1.1386 0.5504 0.07 Uiso 0.5 1 d PR A -1
H10I H 0.2854 1.0088 0.6072 0.07 Uiso 0.5 1 d PR A -1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0204(8) 0.0231(8) 0.0172(8) 0.0001(6) 0.0004(6) -0.0058(6)
C2 0.0221(8) 0.0202(7) 0.0167(8) -0.0002(6) 0.0011(6) -0.0046(6)
C3 0.0198(8) 0.0184(7) 0.0217(8) 0.0015(6) 0.0011(6) -0.0057(6)
C4 0.0230(8) 0.0256(8) 0.0229(8) -0.0012(6) 0.0043(7) -0.0047(7)
C5 0.0181(8) 0.0281(8) 0.0325(9) 0.0020(7) 0.0040(7) -0.0055(7)
C6 0.0206(8) 0.0262(8) 0.0318(9) 0.0015(7) -0.0029(7) -0.0098(7)
C7 0.0254(9) 0.0194(7) 0.0236(8) -0.0007(6) 0.0000(7) -0.0083(6)
C8 0.0197(8) 0.0170(7) 0.0228(8) 0.0000(6) 0.0015(6) -0.0058(6)
C9 0.0193(8) 0.0221(7) 0.0205(8) -0.0052(6) 0.0029(6) -0.0061(6)
C10 0.0178(8) 0.0250(8) 0.0210(8) -0.0019(6) 0.0019(6) -0.0053(6)
C11 0.0181(8) 0.0250(8) 0.0170(8) -0.0049(6) 0.0031(6) -0.0075(6)
C12 0.0171(8) 0.0213(7) 0.0230(8) -0.0048(6) 0.0029(6) -0.0074(6)
C13 0.0187(8) 0.0258(8) 0.0220(8) -0.0039(6) -0.0002(6) -0.0081(6)
C14 0.0233(8) 0.0346(9) 0.0197(8) -0.0067(7) 0.0016(7) -0.0074(7)
C15 0.0226(8) 0.0316(8) 0.0196(8) -0.0075(7) 0.0032(6) -0.0069(7)
C16 0.0243(9) 0.0339(9) 0.0212(8) -0.0020(7) -0.0006(7) -0.0112(7)
C18 0.0255(9) 0.0314(9) 0.0188(8) -0.0057(7) 0.0011(7) -0.0088(8)
C19 0.0345(10) 0.0410(10) 0.0318(10) -0.0050(8) -0.0092(8) -0.0164(8)
C20 0.0401(10) 0.0339(9) 0.0263(9) -0.0078(7) 0.0061(8) -0.0177(8)
C21 0.0255(9) 0.0328(9) 0.0249(9) -0.0036(7) 0.0046(7) -0.0100(7)
C22 0.0283(9) 0.0306(9) 0.0254(9) 0.0026(7) -0.0015(7) -0.0096(7)
C23 0.0431(12) 0.0272(10) 0.0740(16) 0.0082(10) -0.0128(11) -0.0098(9)
C24 0.0532(14) 0.0659(14) 0.0271(11) 0.0076(10) -0.0088(9) -0.0046(11)
C25 0.0270(10) 0.0400(11) 0.0518(13) 0.0090(9) -0.0009(9) -0.0041(8)
C26 0.0194(8) 0.0310(8) 0.0238(8) -0.0025(7) 0.0012(6) -0.0132(7)
C27 0.0286(9) 0.0341(9) 0.0239(9) -0.0039(7) 0.0049(7) -0.0130(7)
C28 0.0333(10) 0.0348(9) 0.0311(10) 0.0028(8) 0.0032(8) -0.0126(8)
C29 0.0281(9) 0.0311(9) 0.0426(11) -0.0032(8) 0.0076(8) -0.0139(8)
C30 0.0339(10) 0.0339(9) 0.0365(10) -0.0122(8) 0.0108(8) -0.0192(8)
C31 0.0278(9) 0.0329(9) 0.0254(9) -0.0064(7) 0.0036(7) -0.0184(7)
C32 0.0452(12) 0.0320(10) 0.0600(14) -0.0013(9) 0.0134(10) -0.0091(9)
N1 0.0173(7) 0.0271(7) 0.0197(7) -0.0050(5) 0.0039(5) -0.0063(5)
N2 0.0308(8) 0.0375(8) 0.0260(8) -0.0033(6) -0.0031(7) -0.0058(7)
O1 0.0217(6) 0.0227(5) 0.0160(5) -0.0023(4) 0.0003(4) -0.0084(4)
O2 0.0240(6) 0.0218(5) 0.0183(6) 0.0006(4) 0.0013(4) -0.0057(4)
O3 0.0257(6) 0.0318(6) 0.0269(6) -0.0077(5) -0.0028(5) -0.0106(5)
O4 0.0188(6) 0.0440(7) 0.0246(6) 0.0004(5) -0.0027(5) -0.0115(5)
O5 0.0206(6) 0.0392(7) 0.0275(6) -0.0036(5) 0.0081(5) -0.0077(5)
Si1 0.0217(2) 0.0232(2) 0.0182(2) -0.00227(17) 0.00199(17) -0.00861(18)
S2 0.0162(2) 0.0320(2) 0.0210(2) -0.00193(16) 0.00255(15) -0.00785(16)
O100 0.119(4) 0.096(3) 0.105(4) -0.031(3) 0.033(3) -0.043(3)
O101 0.0478(14) 0.0400(12) 0.0914(18) -0.0001(11) 0.0116(13) -0.0121(10)
C101 0.057(4) 0.046(3) 0.069(5) 0.001(4) 0.004(4) -0.028(3)
C102 0.049(3) 0.035(2) 0.029(2) -0.0101(17) 0.0104(19) -0.0174(18)
C103 0.029(2) 0.0302(18) 0.035(2) -0.0032(16) -0.0034(17) -0.0108(16)
C104 0.044(3) 0.033(2) 0.061(4) -0.011(3) 0.010(4) -0.010(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 C16 107.99(12) . .
O1 C1 C10 103.24(12) . .
C16 C1 C10 118.13(13) . .
O1 C1 C2 107.02(11) . .
C16 C1 C2 111.27(13) . .
C10 C1 C2 108.40(13) . .
O2 C2 C3 109.18(12) . .
O2 C2 C1 106.84(12) . .
C3 C2 C1 112.21(13) . .
O2 C2 H2 109.5 . .
C3 C2 H2 109.5 . .
C1 C2 H2 109.5 . .
C8 C3 C4 120.12(15) . .
C8 C3 C2 119.84(14) . .
C4 C3 C2 120.05(14) . .
C5 C4 C3 119.92(16) . .
C5 C4 H4 120 . .
C3 C4 H4 120 . .
C4 C5 C6 120.81(15) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C7 119.60(16) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
O3 C7 C6 123.80(15) . .
O3 C7 C8 115.87(14) . .
C6 C7 C8 120.32(15) . .
C3 C8 C7 119.22(14) . .
C3 C8 C9 119.38(14) . .
C7 C8 C9 121.04(14) . .
C8 C9 C10 111.70(13) . .
C8 C9 C11 106.91(12) . .
C10 C9 C11 99.21(12) . .
C8 C9 H9 112.7 . .
C10 C9 H9 112.7 . .
C11 C9 H9 112.7 . .
C1 C10 C9 100.06(12) . .
C1 C10 H10A 111.8 . .
C9 C10 H10A 111.8 . .
C1 C10 H10B 111.8 . .
C9 C10 H10B 111.8 . .
H10A C10 H10B 109.5 . .
O1 C11 C12 107.52(12) . .
O1 C11 N1 111.88(12) . .
C12 C11 N1 109.69(12) . .
O1 C11 C9 103.06(11) . .
C12 C11 C9 115.61(13) . .
N1 C11 C9 108.96(12) . .
C13 C12 C11 123.39(14) . .
C13 C12 H12 118.3 . .
C11 C12 H12 118.3 . .
C12 C13 C18 119.07(14) . .
C12 C13 C14 123.99(14) . .
C18 C13 C14 116.93(14) . .
C13 C14 C15 110.01(13) . .
C13 C14 H14A 109.7 . .
C15 C14 H14A 109.7 . .
C13 C14 H14B 109.7 . .
C15 C14 H14B 109.7 . .
H14A C14 H14B 108.2 . .
N1 C15 C14 113.70(13) . .
N1 C15 H15A 108.8 . .
C14 C15 H15A 108.8 . .
N1 C15 H15B 108.8 . .
C14 C15 H15B 108.8 . .
H15A C15 H15B 107.7 . .
C1 C16 H16A 109.5 . .
C1 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C1 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N2 C18 C13 178.53(18) . .
O3 C19 H19A 109.5 . .
O3 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O3 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Si1 C20 H20A 109.5 . .
Si1 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
Si1 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Si1 C21 H21A 109.5 . .
Si1 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
Si1 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C23 C22 C25 108.64(17) . .
C23 C22 C24 109.23(17) . .
C25 C22 C24 108.66(17) . .
C23 C22 Si1 110.33(13) . .
C25 C22 Si1 111.37(11) . .
C24 C22 Si1 108.57(13) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C31 C26 C27 120.65(16) . .
C31 C26 S2 120.27(12) . .
C27 C26 S2 119.04(13) . .
C28 C27 C26 119.13(16) . .
C28 C27 H27 120.4 . .
C26 C27 H27 120.4 . .
C27 C28 C29 121.32(16) . .
C27 C28 H28 119.3 . .
C29 C28 H28 119.3 . .
C28 C29 C30 118.42(16) . .
C28 C29 C32 121.07(17) . .
C30 C29 C32 120.51(18) . .
C31 C30 C29 121.25(17) . .
C31 C30 H30 119.4 . .
C29 C30 H30 119.4 . .
C30 C31 C26 119.19(16) . .
C30 C31 H31 120.4 . .
C26 C31 H31 120.4 . .
C29 C32 H32A 109.5 . .
C29 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C29 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
C29 C32 H32D 109.5 . .
H32A C32 H32D 141.1 . .
H32B C32 H32D 56.3 . .
H32C C32 H32D 56.3 . .
C29 C32 H32E 109.5 . .
H32A C32 H32E 56.3 . .
H32B C32 H32E 141.1 . .
H32C C32 H32E 56.3 . .
H32D C32 H32E 109.5 . .
C29 C32 H32F 109.5 . .
H32A C32 H32F 56.3 . .
H32B C32 H32F 56.3 . .
H32C C32 H32F 141.1 . .
H32D C32 H32F 109.5 . .
H32E C32 H32F 109.5 . .
C15 N1 C11 110.38(12) . .
C15 N1 S2 116.53(10) . .
C11 N1 S2 121.16(10) . .
C11 O1 C1 110.55(11) . .
C2 O2 Si1 128.72(10) . .
C7 O3 C19 116.73(14) . .
O2 Si1 C20 109.93(7) . .
O2 Si1 C21 110.25(7) . .
C20 Si1 C21 111.30(8) . .
O2 Si1 C22 104.96(7) . .
C20 Si1 C22 111.62(8) . .
C21 Si1 C22 108.60(8) . .
O4 S2 O5 118.86(7) . .
O4 S2 N1 108.17(7) . .
O5 S2 N1 104.80(7) . .
O4 S2 C26 107.99(8) . .
O5 S2 C26 107.94(7) . .
N1 S2 C26 108.73(7) . .
C102 O101 C102 180.0000(10) . 2_676
C102 O101 C103 48.9(2) . 2_676
C102 O101 C103 131.1(2) 2_676 2_676
C102 O101 C103 131.1(2) . .
C102 O101 C103 48.9(2) 2_676 .
C103 O101 C103 180.0(3) 2_676 .
C102 C101 H10C 108.5 . .
C102 C101 H10D 110.1 . .
H10C C101 H10D 109.5 . .
C102 C101 H10E 109.8 . .
H10C C101 H10E 109.5 . .
H10D C101 H10E 109.5 . .
O100 C102 O101 111.7(4) . .
O100 C102 C101 127.4(5) . .
O101 C102 C101 120.9(5) . .
O101 C103 C104 117.7(4) . .
O101 C103 H10F 108 . .
C104 C103 H10F 107.7 . .
O101 C103 H10J 107.9 . .
C104 C103 H10J 107.9 . .
H10F C103 H10J 107.3 . .
C103 C104 H10G 110.1 . .
C103 C104 H10H 109.1 . .
H10G C104 H10H 109.5 . .
C103 C104 H10I 109.3 . .
H10G C104 H10I 109.5 . .
H10H C104 H10I 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.4754(18) .
C1 C16 1.511(2) .
C1 C10 1.516(2) .
C1 C2 1.536(2) .
C2 O2 1.4367(18) .
C2 C3 1.514(2) .
C2 H2 1 .
C3 C8 1.393(2) .
C3 C4 1.396(2) .
C4 C5 1.381(2) .
C4 H4 0.95 .
C5 C6 1.385(3) .
C5 H5 0.95 .
C6 C7 1.391(2) .
C6 H6 0.95 .
C7 O3 1.369(2) .
C7 C8 1.405(2) .
C8 C9 1.515(2) .
C9 C10 1.528(2) .
C9 C11 1.557(2) .
C9 H9 1 .
C10 H10A 0.99 .
C10 H10B 0.99 .
C11 O1 1.4205(19) .
C11 C12 1.502(2) .
C11 N1 1.5035(19) .
C12 C13 1.334(2) .
C12 H12 0.95 .
C13 C18 1.441(2) .
C13 C14 1.506(2) .
C14 C15 1.520(2) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 N1 1.485(2) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C16 H16A 0.98 .
C16 H16B 0.98 .
C16 H16C 0.98 .
C18 N2 1.146(2) .
C19 O3 1.430(2) .
C19 H19A 0.98 .
C19 H19B 0.98 .
C19 H19C 0.98 .
C20 Si1 1.8612(18) .
C20 H20A 0.98 .
C20 H20B 0.98 .
C20 H20C 0.98 .
C21 Si1 1.8627(17) .
C21 H21A 0.98 .
C21 H21B 0.98 .
C21 H21C 0.98 .
C22 C23 1.525(3) .
C22 C25 1.529(3) .
C22 C24 1.538(3) .
C22 Si1 1.8892(17) .
C23 H23A 0.98 .
C23 H23B 0.98 .
C23 H23C 0.98 .
C24 H24A 0.98 .
C24 H24B 0.98 .
C24 H24C 0.98 .
C25 H25A 0.98 .
C25 H25B 0.98 .
C25 H25C 0.98 .
C26 C31 1.389(2) .
C26 C27 1.392(2) .
C26 S2 1.7683(17) .
C27 C28 1.380(3) .
C27 H27 0.95 .
C28 C29 1.391(3) .
C28 H28 0.95 .
C29 C30 1.393(3) .
C29 C32 1.507(3) .
C30 C31 1.380(2) .
C30 H30 0.95 .
C31 H31 0.95 .
C32 H32A 0.98 .
C32 H32B 0.98 .
C32 H32C 0.98 .
C32 H32D 0.98 .
C32 H32E 0.98 .
C32 H32F 0.98 .
N1 S2 1.6605(13) .
O2 Si1 1.6536(11) .
O4 S2 1.4254(12) .
O5 S2 1.4377(12) .
O100 C102 1.157(6) .
O101 C102 1.292(4) .
O101 C102 1.292(4) 2_676
O101 C103 1.362(4) 2_676
O101 C103 1.362(4) .
C101 C102 1.479(9) .
C101 H10C 0.96 .
C101 H10D 0.96 .
C101 H10E 0.96 .
C103 C104 1.504(8) .
C103 H10F 0.9601 .
C103 H10J 0.96 .
C104 H10G 0.96 .
C104 H10H 0.96 .
C104 H10I 0.96 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
O1 C1 C2 O2 178.24(11) .
C16 C1 C2 O2 -64.01(16) .
C10 C1 C2 O2 67.49(15) .
O1 C1 C2 C3 58.61(15) .
C16 C1 C2 C3 176.37(12) .
C10 C1 C2 C3 -52.14(16) .
O2 C2 C3 C8 -101.84(15) .
C1 C2 C3 C8 16.41(19) .
O2 C2 C3 C4 77.97(17) .
C1 C2 C3 C4 -163.79(13) .
C8 C3 C4 C5 1.0(2) .
C2 C3 C4 C5 -178.80(13) .
C3 C4 C5 C6 -0.5(2) .
C4 C5 C6 C7 -0.6(2) .
C5 C6 C7 O3 -177.41(14) .
C5 C6 C7 C8 1.2(2) .
C4 C3 C8 C7 -0.4(2) .
C2 C3 C8 C7 179.38(13) .
C4 C3 C8 C9 172.75(13) .
C2 C3 C8 C9 -7.4(2) .
O3 C7 C8 C3 178.02(13) .
C6 C7 C8 C3 -0.7(2) .
O3 C7 C8 C9 5.0(2) .
C6 C7 C8 C9 -173.72(13) .
C3 C8 C9 C10 33.57(18) .
C7 C8 C9 C10 -153.38(14) .
C3 C8 C9 C11 -73.95(17) .
C7 C8 C9 C11 99.10(16) .
O1 C1 C10 C9 -38.51(14) .
C16 C1 C10 C9 -157.56(13) .
C2 C1 C10 C9 74.76(14) .
C8 C9 C10 C1 -64.83(14) .
C11 C9 C10 C1 47.60(13) .
C8 C9 C11 O1 76.12(14) .
C10 C9 C11 O1 -40.04(14) .
C8 C9 C11 C12 -40.88(17) .
C10 C9 C11 C12 -157.03(13) .
C8 C9 C11 N1 -164.92(12) .
C10 C9 C11 N1 78.93(14) .
O1 C11 C12 C13 141.20(14) .
N1 C11 C12 C13 19.3(2) .
C9 C11 C12 C13 -104.34(17) .
C11 C12 C13 C18 -175.90(14) .
C11 C12 C13 C14 2.8(2) .
C12 C13 C14 C15 6.4(2) .
C18 C13 C14 C15 -174.80(14) .
C13 C14 C15 N1 -39.02(18) .
C31 C26 C27 C28 -1.9(2) .
S2 C26 C27 C28 175.95(13) .
C26 C27 C28 C29 0.6(3) .
C27 C28 C29 C30 1.0(3) .
C27 C28 C29 C32 -179.31(18) .
C28 C29 C30 C31 -1.5(3) .
C32 C29 C30 C31 178.89(17) .
C29 C30 C31 C26 0.2(2) .
C27 C26 C31 C30 1.5(2) .
S2 C26 C31 C30 -176.33(12) .
C14 C15 N1 C11 63.24(16) .
C14 C15 N1 S2 -80.12(15) .
O1 C11 N1 C15 -169.56(12) .
C12 C11 N1 C15 -50.32(16) .
C9 C11 N1 C15 77.14(15) .
O1 C11 N1 S2 -28.15(16) .
C12 C11 N1 S2 91.08(14) .
C9 C11 N1 S2 -141.45(11) .
C12 C11 O1 C1 139.32(12) .
N1 C11 O1 C1 -100.18(13) .
C9 C11 O1 C1 16.74(14) .
C16 C1 O1 C11 139.50(13) .
C10 C1 O1 C11 13.65(15) .
C2 C1 O1 C11 -100.62(13) .
C3 C2 O2 Si1 -105.92(14) .
C1 C2 O2 Si1 132.52(12) .
C6 C7 O3 C19 0.4(2) .
C8 C7 O3 C19 -178.25(13) .
C2 O2 Si1 C20 -40.23(14) .
C2 O2 Si1 C21 82.84(13) .
C2 O2 Si1 C22 -160.39(12) .
C23 C22 Si1 O2 -73.59(15) .
C25 C22 Si1 O2 47.14(15) .
C24 C22 Si1 O2 166.74(13) .
C23 C22 Si1 C20 167.37(14) .
C25 C22 Si1 C20 -71.89(16) .
C24 C22 Si1 C20 47.70(16) .
C23 C22 Si1 C21 44.31(16) .
C25 C22 Si1 C21 165.04(14) .
C24 C22 Si1 C21 -75.37(15) .
C15 N1 S2 O4 -156.42(11) .
C11 N1 S2 O4 64.40(13) .
C15 N1 S2 O5 -28.67(12) .
C11 N1 S2 O5 -167.85(11) .
C15 N1 S2 C26 86.55(12) .
C11 N1 S2 C26 -52.63(13) .
C31 C26 S2 O4 -31.81(15) .
C27 C26 S2 O4 150.33(13) .
C31 C26 S2 O5 -161.50(13) .
C27 C26 S2 O5 20.64(15) .
C31 C26 S2 N1 85.33(14) .
C27 C26 S2 N1 -92.53(14) .
C103 O101 C102 O100 -171.1(5) 2_676
C103 O101 C102 O100 8.9(5) .
C103 O101 C102 C101 6.9(4) 2_676
C103 O101 C102 C101 -173.1(4) .
C102 O101 C103 C104 -179.4(4) .
C102 O101 C103 C104 0.6(4) 2_676
|
1502023.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502023.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502023
loop_
_publ_author_name
'Li, Yuye'
'Shi, Yi'
'Huang, Zhongxing'
'Wu, Xinhu'
'Xu, Pengfei'
'Wang, Jianbo'
'Zhang, Yan'
_publ_section_title
;
Catalytic thia-Sommelet-Hauser rearrangement: application to the
synthesis of oxindoles.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1210
_journal_page_last 1213
_journal_paper_doi 10.1021/ol200091k
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C16 H15 N O S'
_chemical_formula_weight 269.35
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 93.68(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 15.266(3)
_cell_length_b 14.002(3)
_cell_length_c 13.444(3)
_cell_measurement_reflns_used 27378
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 1.34
_cell_volume 2867.8(11)
_computing_cell_refinement Rapid-AUTO
_computing_data_collection 'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement SHELXL-97,(Sheldrick,1997)
_computing_structure_solution SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method \W
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0555
_diffrn_reflns_av_sigmaI/netI 0.0985
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 27378
_diffrn_reflns_theta_full 27.48
_diffrn_reflns_theta_max 27.48
_diffrn_reflns_theta_min 1.34
_diffrn_standards_decay_% 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.217
_exptl_absorpt_correction_T_max 0.9579
_exptl_absorpt_correction_T_min 0.9378
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_density_diffrn 1.248
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1136
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.231
_refine_diff_density_min -0.221
_refine_diff_density_rms 0.052
_refine_ls_extinction_coef 0.0077(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.993
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 348
_refine_ls_number_reflns 6578
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.993
_refine_ls_R_factor_all 0.1018
_refine_ls_R_factor_gt 0.0435
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0923
_refine_ls_wR_factor_ref 0.1245
_reflns_number_gt 3055
_reflns_number_total 6578
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200091k_si_001.cif
_cod_data_source_block lyy1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2867.8(10)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502023
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.63193(16) 0.18487(18) 0.55901(19) 0.0471(7) Uani 1 1 d .
C2 C 0.69278(17) 0.26366(19) 0.52465(18) 0.0494(7) Uani 1 1 d .
C3 C 0.55189(15) 0.30932(18) 0.48014(17) 0.0409(6) Uani 1 1 d .
C4 C 0.47967(19) 0.3610(2) 0.4430(2) 0.0628(8) Uani 1 1 d .
H4 H 0.4856 0.4226 0.4184 0.075 Uiso 1 1 calc R
C5 C 0.39768(19) 0.3171(3) 0.4440(2) 0.0729(9) Uani 1 1 d .
H5 H 0.3482 0.3501 0.4191 0.087 Uiso 1 1 calc R
C6 C 0.38805(19) 0.2275(3) 0.4802(2) 0.0735(9) Uani 1 1 d .
H6 H 0.3326 0.1998 0.4788 0.088 Uiso 1 1 calc R
C7 C 0.46091(17) 0.1770(2) 0.51942(19) 0.0595(8) Uani 1 1 d .
H7 H 0.4544 0.1159 0.5449 0.071 Uiso 1 1 calc R
C8 C 0.54285(15) 0.21887(18) 0.52004(17) 0.0430(6) Uani 1 1 d .
C9 C 0.6614(2) 0.08613(19) 0.5257(2) 0.0740(9) Uani 1 1 d .
H9A H 0.6238 0.0382 0.5513 0.111 Uiso 1 1 calc R
H9B H 0.7208 0.0750 0.5507 0.111 Uiso 1 1 calc R
H9C H 0.6579 0.0832 0.4543 0.111 Uiso 1 1 calc R
C10 C 0.6761(2) 0.4260(2) 0.4519(2) 0.0759(9) Uani 1 1 d .
H10A H 0.7390 0.4248 0.4598 0.114 Uiso 1 1 calc R
H10B H 0.6542 0.4768 0.4914 0.114 Uiso 1 1 calc R
H10C H 0.6580 0.4364 0.3830 0.114 Uiso 1 1 calc R
C11 C 0.59588(17) 0.29884(19) 0.72375(17) 0.0463(6) Uani 1 1 d .
C12 C 0.50750(19) 0.3082(2) 0.7406(2) 0.0642(8) Uani 1 1 d .
H12 H 0.4716 0.2545 0.7385 0.077 Uiso 1 1 calc R
C13 C 0.4724(2) 0.3965(3) 0.7603(2) 0.0761(10) Uani 1 1 d .
H13 H 0.4131 0.4025 0.7709 0.091 Uiso 1 1 calc R
C14 C 0.5255(3) 0.4750(3) 0.7642(2) 0.0789(10) Uani 1 1 d .
H14 H 0.5019 0.5346 0.7775 0.095 Uiso 1 1 calc R
C15 C 0.6140(2) 0.4673(2) 0.7486(2) 0.0704(9) Uani 1 1 d .
H15 H 0.6495 0.5213 0.7515 0.084 Uiso 1 1 calc R
C16 C 0.64945(18) 0.3790(2) 0.72864(18) 0.0543(7) Uani 1 1 d .
H16 H 0.7089 0.3734 0.7185 0.065 Uiso 1 1 calc R
C17 C 0.10927(15) 0.03896(17) 0.2499(2) 0.0470(7) Uani 1 1 d .
C18 C 0.09154(17) 0.06296(18) 0.1390(2) 0.0501(7) Uani 1 1 d .
C19 C -0.02056(14) 0.12562(16) 0.22129(18) 0.0383(6) Uani 1 1 d .
C20 C -0.09604(16) 0.17358(17) 0.2409(2) 0.0472(7) Uani 1 1 d .
H20 H -0.1305 0.2035 0.1906 0.057 Uiso 1 1 calc R
C21 C -0.11860(17) 0.17540(19) 0.3390(2) 0.0587(8) Uani 1 1 d .
H21 H -0.1692 0.2075 0.3547 0.070 Uiso 1 1 calc R
C22 C -0.0685(2) 0.1313(2) 0.4135(2) 0.0602(8) Uani 1 1 d .
H22 H -0.0859 0.1327 0.4786 0.072 Uiso 1 1 calc R
C23 C 0.00799(18) 0.08453(19) 0.3922(2) 0.0559(7) Uani 1 1 d .
H23 H 0.0428 0.0552 0.4427 0.067 Uiso 1 1 calc R
C24 C 0.03166(15) 0.08222(16) 0.29547(19) 0.0409(6) Uani 1 1 d .
C25 C 0.11915(18) -0.06904(18) 0.2652(2) 0.0709(9) Uani 1 1 d .
H25A H 0.1330 -0.0822 0.3345 0.106 Uiso 1 1 calc R
H25B H 0.1655 -0.0924 0.2268 0.106 Uiso 1 1 calc R
H25C H 0.0652 -0.1002 0.2439 0.106 Uiso 1 1 calc R
C26 C -0.01990(19) 0.1518(2) 0.0346(2) 0.0727(9) Uani 1 1 d .
H26A H -0.0121 0.2198 0.0344 0.109 Uiso 1 1 calc R
H26B H -0.0813 0.1371 0.0258 0.109 Uiso 1 1 calc R
H26C H 0.0103 0.1240 -0.0188 0.109 Uiso 1 1 calc R
C27 C 0.19263(16) 0.21727(19) 0.2682(2) 0.0517(7) Uani 1 1 d .
C28 C 0.16236(17) 0.2786(2) 0.3383(2) 0.0631(8) Uani 1 1 d .
H28 H 0.1512 0.2558 0.4013 0.076 Uiso 1 1 calc R
C29 C 0.14850(19) 0.3736(2) 0.3156(3) 0.0765(10) Uani 1 1 d .
H29 H 0.1292 0.4148 0.3639 0.092 Uiso 1 1 calc R
C30 C 0.16273(19) 0.4076(2) 0.2235(3) 0.0765(10) Uani 1 1 d .
H30 H 0.1526 0.4717 0.2087 0.092 Uiso 1 1 calc R
C31 C 0.1919(2) 0.3479(2) 0.1529(3) 0.0853(11) Uani 1 1 d .
H31 H 0.2010 0.3711 0.0895 0.102 Uiso 1 1 calc R
C32 C 0.2079(2) 0.2527(2) 0.1753(2) 0.0730(9) Uani 1 1 d .
H32 H 0.2290 0.2125 0.1274 0.088 Uiso 1 1 calc R
N1 N 0.64113(13) 0.33514(15) 0.48447(15) 0.0487(6) Uani 1 1 d .
N2 N 0.01546(12) 0.11308(14) 0.12909(15) 0.0440(5) Uani 1 1 d .
O1 O 0.77239(11) 0.26440(15) 0.53340(14) 0.0755(6) Uani 1 1 d .
O2 O 0.13630(13) 0.04126(15) 0.07087(16) 0.0754(6) Uani 1 1 d .
S1 S 0.64052(5) 0.18546(5) 0.69712(5) 0.0584(2) Uani 1 1 d .
S2 S 0.21335(4) 0.09492(5) 0.29672(6) 0.0662(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0476(15) 0.0433(15) 0.0490(16) -0.0021(13) -0.0083(12) 0.0037(13)
C2 0.0460(16) 0.0593(18) 0.0428(17) -0.0126(14) 0.0017(13) -0.0022(14)
C3 0.0427(15) 0.0443(15) 0.0358(14) -0.0002(12) 0.0028(12) -0.0014(12)
C4 0.069(2) 0.0638(19) 0.0544(19) 0.0058(15) -0.0055(16) 0.0102(17)
C5 0.0432(18) 0.101(3) 0.073(2) -0.001(2) -0.0085(15) 0.0129(19)
C6 0.0424(17) 0.105(3) 0.073(2) -0.002(2) -0.0025(16) -0.0133(18)
C7 0.0544(17) 0.070(2) 0.0533(18) 0.0042(15) -0.0027(14) -0.0207(16)
C8 0.0404(14) 0.0507(16) 0.0374(15) -0.0015(12) -0.0016(11) -0.0064(12)
C9 0.090(2) 0.0556(19) 0.074(2) -0.0145(17) -0.0109(18) 0.0137(17)
C10 0.096(2) 0.064(2) 0.071(2) 0.0014(17) 0.0238(18) -0.0327(18)
C11 0.0500(16) 0.0592(18) 0.0294(14) 0.0033(13) 0.0008(12) 0.0075(14)
C12 0.0572(18) 0.085(2) 0.0510(18) 0.0052(17) 0.0092(14) -0.0051(18)
C13 0.062(2) 0.108(3) 0.059(2) 0.000(2) 0.0152(16) 0.026(2)
C14 0.109(3) 0.080(3) 0.048(2) -0.0035(18) 0.001(2) 0.041(2)
C15 0.087(3) 0.065(2) 0.057(2) -0.0061(16) -0.0025(18) 0.0010(19)
C16 0.0529(17) 0.0594(19) 0.0497(17) -0.0053(14) -0.0023(14) 0.0014(15)
C17 0.0385(14) 0.0408(15) 0.0611(18) 0.0137(13) -0.0001(13) 0.0036(12)
C18 0.0442(15) 0.0455(16) 0.0615(19) 0.0008(14) 0.0097(14) 0.0061(13)
C19 0.0338(13) 0.0324(13) 0.0490(16) 0.0002(12) 0.0050(12) -0.0006(11)
C20 0.0433(15) 0.0400(15) 0.0582(19) 0.0011(13) 0.0025(13) 0.0003(12)
C21 0.0520(17) 0.0470(17) 0.080(2) -0.0130(16) 0.0237(16) -0.0032(14)
C22 0.069(2) 0.0621(19) 0.0515(19) -0.0100(15) 0.0165(16) -0.0185(16)
C23 0.0596(18) 0.0534(18) 0.0543(19) 0.0088(14) -0.0006(15) -0.0115(15)
C24 0.0398(14) 0.0362(14) 0.0468(16) 0.0072(12) 0.0028(12) -0.0010(11)
C25 0.0633(19) 0.0468(18) 0.102(3) 0.0167(17) 0.0044(18) 0.0122(15)
C26 0.072(2) 0.094(2) 0.0517(19) 0.0172(17) 0.0019(16) 0.0222(18)
C27 0.0366(14) 0.0524(17) 0.066(2) 0.0099(16) -0.0017(14) -0.0031(13)
C28 0.0511(17) 0.069(2) 0.070(2) 0.0024(18) 0.0090(15) -0.0057(16)
C29 0.064(2) 0.064(2) 0.105(3) -0.009(2) 0.024(2) 0.0010(17)
C30 0.071(2) 0.0469(19) 0.112(3) 0.004(2) 0.015(2) 0.0058(16)
C31 0.108(3) 0.061(2) 0.088(3) 0.023(2) 0.020(2) -0.003(2)
C32 0.084(2) 0.055(2) 0.082(2) -0.0012(18) 0.0255(19) 0.0000(17)
N1 0.0496(13) 0.0506(14) 0.0468(14) -0.0013(11) 0.0090(11) -0.0124(11)
N2 0.0408(11) 0.0479(13) 0.0435(13) 0.0069(10) 0.0039(10) 0.0112(10)
O1 0.0334(10) 0.1107(17) 0.0828(15) -0.0224(13) 0.0060(10) -0.0036(11)
O2 0.0696(13) 0.0824(15) 0.0770(15) -0.0038(12) 0.0255(12) 0.0254(11)
S1 0.0705(5) 0.0561(5) 0.0470(4) 0.0054(4) -0.0088(4) 0.0108(4)
S2 0.0392(4) 0.0591(5) 0.0985(6) 0.0209(4) -0.0098(4) 0.0040(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C1 C9 117.4(2)
C8 C1 C2 102.7(2)
C9 C1 C2 111.6(2)
C8 C1 S1 110.62(18)
C9 C1 S1 107.09(18)
C2 C1 S1 107.07(16)
O1 C2 N1 125.6(3)
O1 C2 C1 126.8(3)
N1 C2 C1 107.5(2)
C4 C3 C8 121.4(2)
C4 C3 N1 128.8(2)
C8 C3 N1 109.8(2)
C3 C4 C5 117.4(3)
C3 C4 H4 121.3
C5 C4 H4 121.3
C6 C5 C4 121.9(3)
C6 C5 H5 119.0
C4 C5 H5 119.0
C5 C6 C7 120.2(3)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 119.2(3)
C8 C7 H7 120.4
C6 C7 H7 120.4
C7 C8 C3 119.9(2)
C7 C8 C1 131.8(2)
C3 C8 C1 108.3(2)
C1 C9 H9A 109.5
C1 C9 H9B 109.5
H9A C9 H9B 109.5
C1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 119.4(3)
C16 C11 S1 120.0(2)
C12 C11 S1 120.5(2)
C13 C12 C11 120.6(3)
C13 C12 H12 119.7
C11 C12 H12 119.7
C14 C13 C12 119.5(3)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C15 120.9(3)
C13 C14 H14 119.6
C15 C14 H14 119.6
C16 C15 C14 119.8(3)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C11 119.7(3)
C15 C16 H16 120.1
C11 C16 H16 120.1
C24 C17 C25 114.7(2)
C24 C17 C18 102.36(19)
C25 C17 C18 110.9(2)
C24 C17 S2 112.06(18)
C25 C17 S2 107.34(17)
C18 C17 S2 109.41(17)
O2 C18 N2 125.0(3)
O2 C18 C17 127.2(2)
N2 C18 C17 107.8(2)
C20 C19 C24 122.0(2)
C20 C19 N2 127.9(2)
C24 C19 N2 110.1(2)
C19 C20 C21 117.1(2)
C19 C20 H20 121.5
C21 C20 H20 121.5
C22 C21 C20 121.9(3)
C22 C21 H21 119.1
C20 C21 H21 119.1
C21 C22 C23 120.1(3)
C21 C22 H22 120.0
C23 C22 H22 120.0
C24 C23 C22 118.9(3)
C24 C23 H23 120.5
C22 C23 H23 120.5
C23 C24 C19 120.0(2)
C23 C24 C17 131.4(2)
C19 C24 C17 108.6(2)
C17 C25 H25A 109.5
C17 C25 H25B 109.5
H25A C25 H25B 109.5
C17 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
N2 C26 H26A 109.5
N2 C26 H26B 109.5
H26A C26 H26B 109.5
N2 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C32 C27 C28 118.7(3)
C32 C27 S2 120.3(2)
C28 C27 S2 121.0(2)
C27 C28 C29 120.2(3)
C27 C28 H28 119.9
C29 C28 H28 119.9
C30 C29 C28 120.6(3)
C30 C29 H29 119.7
C28 C29 H29 119.7
C29 C30 C31 120.0(3)
C29 C30 H30 120.0
C31 C30 H30 120.0
C30 C31 C32 120.0(3)
C30 C31 H31 120.0
C32 C31 H31 120.0
C27 C32 C31 120.5(3)
C27 C32 H32 119.8
C31 C32 H32 119.8
C2 N1 C3 111.2(2)
C2 N1 C10 123.1(2)
C3 N1 C10 125.7(2)
C18 N2 C19 111.1(2)
C18 N2 C26 123.2(2)
C19 N2 C26 125.6(2)
C11 S1 C1 101.71(11)
C27 S2 C17 101.42(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.503(3)
C1 C9 1.529(3)
C1 C2 1.532(3)
C1 S1 1.853(3)
C2 O1 1.213(3)
C2 N1 1.364(3)
C3 C4 1.385(3)
C3 C8 1.386(3)
C3 N1 1.407(3)
C4 C5 1.396(4)
C4 H4 0.9300
C5 C6 1.356(4)
C5 H5 0.9300
C6 C7 1.393(4)
C6 H6 0.9300
C7 C8 1.381(3)
C7 H7 0.9300
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 N1 1.458(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C16 1.388(3)
C11 C12 1.388(4)
C11 S1 1.773(3)
C12 C13 1.380(4)
C12 H12 0.9300
C13 C14 1.364(4)
C13 H13 0.9300
C14 C15 1.385(4)
C14 H14 0.9300
C15 C16 1.382(4)
C15 H15 0.9300
C16 H16 0.9300
C17 C24 1.496(3)
C17 C25 1.532(3)
C17 C18 1.535(4)
C17 S2 1.846(2)
C18 O2 1.216(3)
C18 N2 1.356(3)
C19 C20 1.374(3)
C19 C24 1.377(3)
C19 N2 1.399(3)
C20 C21 1.384(4)
C20 H20 0.9300
C21 C22 1.368(4)
C21 H21 0.9300
C22 C23 1.385(4)
C22 H22 0.9300
C23 C24 1.373(3)
C23 H23 0.9300
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
C26 N2 1.453(3)
C26 H26A 0.9600
C26 H26B 0.9600
C26 H26C 0.9600
C27 C32 1.377(4)
C27 C28 1.377(4)
C27 S2 1.779(3)
C28 C29 1.379(4)
C28 H28 0.9300
C29 C30 1.357(4)
C29 H29 0.9300
C30 C31 1.361(4)
C30 H30 0.9300
C31 C32 1.385(4)
C31 H31 0.9300
C32 H32 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 C1 C2 O1 -174.9(2)
C9 C1 C2 O1 -48.3(3)
S1 C1 C2 O1 68.6(3)
C8 C1 C2 N1 6.8(3)
C9 C1 C2 N1 133.5(2)
S1 C1 C2 N1 -109.68(19)
C8 C3 C4 C5 -2.3(4)
N1 C3 C4 C5 177.5(2)
C3 C4 C5 C6 0.4(4)
C4 C5 C6 C7 1.1(5)
C5 C6 C7 C8 -0.6(4)
C6 C7 C8 C3 -1.2(4)
C6 C7 C8 C1 178.0(3)
C4 C3 C8 C7 2.7(4)
N1 C3 C8 C7 -177.1(2)
C4 C3 C8 C1 -176.6(2)
N1 C3 C8 C1 3.5(3)
C9 C1 C8 C7 51.8(4)
C2 C1 C8 C7 174.5(3)
S1 C1 C8 C7 -71.5(3)
C9 C1 C8 C3 -129.0(3)
C2 C1 C8 C3 -6.2(3)
S1 C1 C8 C3 107.7(2)
C16 C11 C12 C13 1.1(4)
S1 C11 C12 C13 -179.3(2)
C11 C12 C13 C14 -0.6(4)
C12 C13 C14 C15 0.0(5)
C13 C14 C15 C16 0.1(5)
C14 C15 C16 C11 0.4(4)
C12 C11 C16 C15 -1.0(4)
S1 C11 C16 C15 179.4(2)
C24 C17 C18 O2 -178.8(3)
C25 C17 C18 O2 -56.0(4)
S2 C17 C18 O2 62.2(3)
C24 C17 C18 N2 0.7(3)
C25 C17 C18 N2 123.5(2)
S2 C17 C18 N2 -118.28(19)
C24 C19 C20 C21 -1.0(4)
N2 C19 C20 C21 179.5(2)
C19 C20 C21 C22 -0.2(4)
C20 C21 C22 C23 1.2(4)
C21 C22 C23 C24 -0.9(4)
C22 C23 C24 C19 -0.3(4)
C22 C23 C24 C17 179.4(2)
C20 C19 C24 C23 1.3(4)
N2 C19 C24 C23 -179.1(2)
C20 C19 C24 C17 -178.5(2)
N2 C19 C24 C17 1.1(3)
C25 C17 C24 C23 59.0(4)
C18 C17 C24 C23 179.2(3)
S2 C17 C24 C23 -63.7(3)
C25 C17 C24 C19 -121.3(2)
C18 C17 C24 C19 -1.1(2)
S2 C17 C24 C19 116.02(19)
C32 C27 C28 C29 -0.5(4)
S2 C27 C28 C29 178.6(2)
C27 C28 C29 C30 1.3(4)
C28 C29 C30 C31 -0.7(5)
C29 C30 C31 C32 -0.7(5)
C28 C27 C32 C31 -0.8(4)
S2 C27 C32 C31 -180.0(2)
C30 C31 C32 C27 1.5(5)
O1 C2 N1 C3 176.5(2)
C1 C2 N1 C3 -5.2(3)
O1 C2 N1 C10 -4.0(4)
C1 C2 N1 C10 174.3(2)
C4 C3 N1 C2 -178.7(2)
C8 C3 N1 C2 1.1(3)
C4 C3 N1 C10 1.9(4)
C8 C3 N1 C10 -178.3(2)
O2 C18 N2 C19 179.5(2)
C17 C18 N2 C19 -0.1(3)
O2 C18 N2 C26 -3.4(4)
C17 C18 N2 C26 177.1(2)
C20 C19 N2 C18 179.0(2)
C24 C19 N2 C18 -0.6(3)
C20 C19 N2 C26 1.9(4)
C24 C19 N2 C26 -177.7(2)
C16 C11 S1 C1 -86.8(2)
C12 C11 S1 C1 93.6(2)
C8 C1 S1 C11 -46.1(2)
C9 C1 S1 C11 -175.18(18)
C2 C1 S1 C11 65.05(19)
C32 C27 S2 C17 -85.7(2)
C28 C27 S2 C17 95.2(2)
C24 C17 S2 C27 -55.8(2)
C25 C17 S2 C27 177.4(2)
C18 C17 S2 C27 57.0(2)
|
1502024.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502024.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502024
loop_
_publ_author_name
'Rajeshwaran, Ganesan Gobi'
'Mohanakrishnan, Arasambattu K.'
_publ_section_title
;
Synthetic studies on indolocarbazoles: total synthesis of staurosporine
aglycon.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1418
_journal_page_last 1421
_journal_paper_doi 10.1021/ol200094b
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C27 H19 Cl N2 O6 S'
_chemical_formula_weight 534.95
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 75.603(5)
_cell_angle_beta 79.653(5)
_cell_angle_gamma 86.555(5)
_cell_formula_units_Z 2
_cell_length_a 8.1141(18)
_cell_length_b 12.333(3)
_cell_length_c 12.540(3)
_cell_measurement_reflns_used 2680
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 22.91
_cell_measurement_theta_min 2.55
_cell_volume 1195.6(5)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics platon
_computing_publication_material 'mercury 2.3'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0285
_diffrn_reflns_av_sigmaI/netI 0.0358
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 11096
_diffrn_reflns_theta_full 24.65
_diffrn_reflns_theta_max 24.65
_diffrn_reflns_theta_min 1.70
_exptl_absorpt_coefficient_mu 0.296
_exptl_absorpt_correction_T_max 0.9654
_exptl_absorpt_correction_T_min 0.9542
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour pale-yellow
_exptl_crystal_density_diffrn 1.486
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 552
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.12
_refine_diff_density_max 0.281
_refine_diff_density_min -1.157
_refine_diff_density_rms 0.083
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 336
_refine_ls_number_reflns 4038
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.034
_refine_ls_R_factor_all 0.0913
_refine_ls_R_factor_gt 0.0700
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1289P)^2^+1.5922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2115
_refine_ls_wR_factor_ref 0.2307
_reflns_number_gt 2966
_reflns_number_total 4038
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200094b_si_001.cif
_cod_data_source_block compound_18c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'P-1 '
_cod_database_code 1502024
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0357(6) 0.4567(4) 0.3491(4) 0.0597(12) Uani 1 1 d .
H1 H 0.0849 0.3875 0.3445 0.072 Uiso 1 1 calc R
C2 C -0.1343(7) 0.4674(6) 0.3803(4) 0.0741(16) Uani 1 1 d .
H2 H -0.2014 0.4051 0.3954 0.089 Uiso 1 1 calc R
C3 C -0.2062(7) 0.5683(5) 0.3895(4) 0.0678(15) Uani 1 1 d .
H3 H -0.3216 0.5745 0.4104 0.081 Uiso 1 1 calc R
C4 C -0.1081(8) 0.6602(5) 0.3677(5) 0.0727(16) Uani 1 1 d .
H4 H -0.1574 0.7285 0.3757 0.087 Uiso 1 1 calc R
C5 C 0.0617(7) 0.6534(4) 0.3344(4) 0.0586(12) Uani 1 1 d .
H5 H 0.1280 0.7162 0.3187 0.070 Uiso 1 1 calc R
C6 C 0.1316(6) 0.5509(4) 0.3249(3) 0.0465(10) Uani 1 1 d .
S7 S 0.34908(13) 0.54047(9) 0.27938(9) 0.0464(3) Uani 1 1 d .
O8 O 0.4174(4) 0.4477(3) 0.3515(3) 0.0572(8) Uani 1 1 d .
O9 O 0.4210(4) 0.6483(3) 0.2564(3) 0.0640(9) Uani 1 1 d .
N10 N 0.3637(4) 0.5070(3) 0.1567(3) 0.0422(8) Uani 1 1 d .
C11 C 0.3089(5) 0.5841(3) 0.0631(3) 0.0435(10) Uani 1 1 d .
C12 C 0.3079(6) 0.7004(4) 0.0367(4) 0.0537(11) Uani 1 1 d .
H12 H 0.3467 0.7397 0.0814 0.064 Uiso 1 1 calc R
C13 C 0.2470(6) 0.7549(4) -0.0585(4) 0.0625(14) Uani 1 1 d .
H13 H 0.2413 0.8327 -0.0772 0.075 Uiso 1 1 calc R
C14 C 0.1936(7) 0.6965(4) -0.1272(4) 0.0653(14) Uani 1 1 d .
H14 H 0.1543 0.7358 -0.1914 0.078 Uiso 1 1 calc R
C15 C 0.1982(6) 0.5814(4) -0.1017(4) 0.0536(11) Uani 1 1 d .
H15 H 0.1641 0.5427 -0.1487 0.064 Uiso 1 1 calc R
C16 C 0.2551(5) 0.5235(3) -0.0040(3) 0.0424(10) Uani 1 1 d .
C17 C 0.2716(5) 0.4040(3) 0.0494(3) 0.0391(9) Uani 1 1 d .
C18 C 0.2370(5) 0.3074(3) 0.0196(3) 0.0418(9) Uani 1 1 d .
C19 C 0.1736(6) 0.3144(4) -0.0879(4) 0.0549(12) Uani 1 1 d .
H19A H 0.1507 0.2405 -0.0928 0.082 Uiso 1 1 calc R
H19B H 0.2571 0.3479 -0.1501 0.082 Uiso 1 1 calc R
H19C H 0.0728 0.3592 -0.0892 0.082 Uiso 1 1 calc R
C20 C 0.2590(5) 0.2049(3) 0.0949(3) 0.0428(10) Uani 1 1 d .
C21 C 0.2093(6) 0.0980(4) 0.0733(4) 0.0539(12) Uani 1 1 d .
O22 O 0.2691(5) 0.0592(3) -0.0030(3) 0.0787(11) Uani 1 1 d .
O23 O 0.0893(4) 0.0495(3) 0.1561(3) 0.0634(9) Uani 1 1 d .
C24 C 0.0450(10) -0.0630(5) 0.1576(6) 0.100(2) Uani 1 1 d .
H24A H 0.0132 -0.0634 0.0875 0.151 Uiso 1 1 calc R
H24B H -0.0470 -0.0878 0.2170 0.151 Uiso 1 1 calc R
H24C H 0.1396 -0.1125 0.1690 0.151 Uiso 1 1 calc R
C25 C 0.3194(5) 0.1989(3) 0.1940(3) 0.0415(9) Uani 1 1 d .
C26 C 0.3623(5) 0.2952(3) 0.2201(3) 0.0426(10) Uani 1 1 d .
H26 H 0.4082 0.2916 0.2837 0.051 Uiso 1 1 calc R
C27 C 0.3343(5) 0.3973(3) 0.1477(3) 0.0374(9) Uani 1 1 d .
C28 C 0.3506(5) 0.0876(3) 0.2689(4) 0.0456(10) Uani 1 1 d .
C29 C 0.4662(6) 0.0139(4) 0.2291(4) 0.0536(11) Uani 1 1 d .
H29 H 0.5201 0.0336 0.1552 0.064 Uiso 1 1 calc R
C30 C 0.5040(6) -0.0889(4) 0.2968(5) 0.0643(14) Uani 1 1 d .
H30 H 0.5800 -0.1379 0.2676 0.077 Uiso 1 1 calc R
C31 C 0.4283(6) -0.1178(4) 0.4073(4) 0.0605(13) Uani 1 1 d .
C32 C 0.3140(6) -0.0478(4) 0.4495(4) 0.0594(13) Uani 1 1 d .
H32 H 0.2636 -0.0674 0.5242 0.071 Uiso 1 1 calc R
C33 C 0.2726(6) 0.0526(4) 0.3809(4) 0.0493(11) Uani 1 1 d .
N34 N 0.1352(6) 0.1196(4) 0.4285(4) 0.0630(11) Uani 1 1 d .
O35 O 0.0458(5) 0.1759(3) 0.3691(3) 0.0797(12) Uani 1 1 d .
O36 O 0.1136(7) 0.1090(4) 0.5300(4) 0.1045(15) Uani 1 1 d .
Cl37 Cl 0.4751(2) -0.24007(14) 0.49531(16) 0.0988(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.055(3) 0.059(3) 0.064(3) -0.021(2) 0.002(2) -0.003(2)
C2 0.061(3) 0.101(5) 0.060(3) -0.023(3) 0.003(3) -0.023(3)
C3 0.055(3) 0.104(5) 0.044(3) -0.022(3) -0.005(2) 0.017(3)
C4 0.073(4) 0.079(4) 0.063(3) -0.020(3) -0.005(3) 0.023(3)
C5 0.065(3) 0.053(3) 0.057(3) -0.015(2) -0.008(2) 0.008(2)
C6 0.051(3) 0.052(3) 0.037(2) -0.0130(19) -0.0081(19) 0.001(2)
S7 0.0460(6) 0.0472(7) 0.0515(7) -0.0187(5) -0.0127(5) -0.0013(5)
O8 0.062(2) 0.063(2) 0.0553(19) -0.0233(16) -0.0226(16) 0.0063(16)
O9 0.066(2) 0.055(2) 0.080(2) -0.0280(18) -0.0145(18) -0.0131(16)
N10 0.0430(19) 0.0404(19) 0.0428(19) -0.0101(15) -0.0052(15) -0.0042(15)
C11 0.034(2) 0.044(2) 0.047(2) -0.0056(19) 0.0012(18) -0.0023(17)
C12 0.048(3) 0.041(2) 0.066(3) -0.008(2) 0.002(2) -0.005(2)
C13 0.056(3) 0.046(3) 0.071(3) 0.005(2) 0.002(3) -0.004(2)
C14 0.063(3) 0.061(3) 0.058(3) 0.012(3) -0.009(2) 0.002(2)
C15 0.050(3) 0.059(3) 0.045(2) -0.001(2) -0.007(2) -0.005(2)
C16 0.035(2) 0.044(2) 0.043(2) -0.0034(18) -0.0007(17) -0.0023(17)
C17 0.035(2) 0.042(2) 0.038(2) -0.0083(17) -0.0028(16) -0.0015(17)
C18 0.037(2) 0.047(2) 0.040(2) -0.0092(18) -0.0055(17) -0.0048(17)
C19 0.061(3) 0.061(3) 0.047(2) -0.012(2) -0.018(2) -0.007(2)
C20 0.040(2) 0.043(2) 0.045(2) -0.0123(19) -0.0023(18) -0.0037(18)
C21 0.059(3) 0.045(3) 0.064(3) -0.018(2) -0.024(2) 0.002(2)
O22 0.102(3) 0.069(2) 0.077(2) -0.041(2) -0.015(2) 0.003(2)
O23 0.067(2) 0.0470(19) 0.077(2) -0.0121(16) -0.0141(19) -0.0174(16)
C24 0.140(6) 0.049(3) 0.118(6) -0.004(3) -0.048(5) -0.034(4)
C25 0.044(2) 0.039(2) 0.041(2) -0.0093(17) -0.0057(18) -0.0002(17)
C26 0.043(2) 0.047(2) 0.040(2) -0.0131(19) -0.0087(18) 0.0003(18)
C27 0.034(2) 0.039(2) 0.038(2) -0.0097(17) -0.0006(16) -0.0017(16)
C28 0.048(2) 0.041(2) 0.049(2) -0.0092(19) -0.012(2) -0.0023(19)
C29 0.057(3) 0.044(3) 0.056(3) -0.006(2) -0.008(2) 0.001(2)
C30 0.056(3) 0.052(3) 0.084(4) -0.017(3) -0.014(3) 0.011(2)
C31 0.057(3) 0.054(3) 0.064(3) 0.000(2) -0.014(2) -0.004(2)
C32 0.068(3) 0.055(3) 0.050(3) -0.001(2) -0.009(2) -0.009(2)
C33 0.053(3) 0.044(2) 0.048(2) -0.006(2) -0.007(2) -0.007(2)
N34 0.071(3) 0.051(2) 0.059(3) -0.013(2) 0.012(2) -0.010(2)
O35 0.070(2) 0.068(2) 0.081(3) 0.003(2) 0.007(2) 0.014(2)
O36 0.132(4) 0.109(4) 0.069(3) -0.033(3) 0.004(3) 0.012(3)
Cl37 0.1060(13) 0.0732(11) 0.1065(13) 0.0015(9) -0.0272(10) 0.0112(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.3(5)
C3 C2 C1 120.9(5)
C2 C3 C4 119.8(5)
C3 C4 C5 121.0(5)
C4 C5 C6 118.2(5)
C5 C6 C1 121.7(4)
C5 C6 S7 119.1(4)
C1 C6 S7 119.2(4)
O8 S7 O9 119.8(2)
O8 S7 N10 106.24(18)
O9 S7 N10 106.76(19)
O8 S7 C6 109.8(2)
O9 S7 C6 109.2(2)
N10 S7 C6 103.83(19)
C27 N10 C11 107.0(3)
C27 N10 S7 122.9(3)
C11 N10 S7 120.9(3)
C12 C11 C16 122.5(4)
C12 C11 N10 128.7(4)
C16 C11 N10 108.8(3)
C13 C12 C11 117.1(5)
C12 C13 C14 121.6(5)
C15 C14 C13 120.9(5)
C14 C15 C16 118.8(5)
C11 C16 C15 119.1(4)
C11 C16 C17 107.7(4)
C15 C16 C17 133.2(4)
C18 C17 C27 120.7(4)
C18 C17 C16 132.4(4)
C27 C17 C16 106.9(4)
C17 C18 C20 117.2(4)
C17 C18 C19 120.8(4)
C20 C18 C19 122.0(4)
C25 C20 C18 121.7(4)
C25 C20 C21 118.1(4)
C18 C20 C21 120.1(4)
O22 C21 O23 124.3(5)
O22 C21 C20 126.3(5)
O23 C21 C20 109.4(4)
C21 O23 C24 116.4(5)
C26 C25 C20 120.7(4)
C26 C25 C28 119.1(4)
C20 C25 C28 120.1(4)
C25 C26 C27 117.6(4)
C26 C27 C17 121.9(4)
C26 C27 N10 128.6(4)
C17 C27 N10 109.5(3)
C29 C28 C33 116.3(4)
C29 C28 C25 119.6(4)
C33 C28 C25 124.0(4)
C28 C29 C30 121.7(5)
C31 C30 C29 119.8(5)
C32 C31 C30 120.3(5)
C32 C31 Cl37 117.8(4)
C30 C31 Cl37 121.9(4)
C31 C32 C33 119.7(5)
C32 C33 C28 122.1(4)
C32 C33 N34 117.1(4)
C28 C33 N34 120.7(4)
O35 N34 O36 123.4(5)
O35 N34 C33 119.7(4)
O36 N34 C33 116.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.372(7)
C1 C6 1.378(6)
C2 C3 1.364(8)
C3 C4 1.368(8)
C4 C5 1.370(8)
C5 C6 1.377(6)
C6 S7 1.761(5)
S7 O8 1.422(3)
S7 O9 1.426(3)
S7 N10 1.672(4)
N10 C27 1.423(5)
N10 C11 1.436(5)
C11 C12 1.390(6)
C11 C16 1.392(6)
C12 C13 1.375(7)
C13 C14 1.389(8)
C14 C15 1.376(7)
C15 C16 1.397(6)
C16 C17 1.468(6)
C17 C18 1.392(6)
C17 C27 1.398(6)
C18 C20 1.401(6)
C18 C19 1.509(6)
C20 C25 1.400(6)
C20 C21 1.501(6)
C21 O22 1.189(6)
C21 O23 1.335(6)
O23 C24 1.450(6)
C25 C26 1.386(6)
C25 C28 1.493(6)
C26 C27 1.390(6)
C28 C29 1.382(6)
C28 C33 1.405(6)
C29 C30 1.391(6)
C30 C31 1.378(7)
C31 C32 1.356(7)
C31 Cl37 1.700(5)
C32 C33 1.382(6)
C33 N34 1.476(6)
N34 O35 1.199(6)
N34 O36 1.228(6)
|
1502025.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502025.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502025
loop_
_publ_author_name
'Rajeshwaran, Ganesan Gobi'
'Mohanakrishnan, Arasambattu K.'
_publ_section_title
;
Synthetic studies on indolocarbazoles: total synthesis of staurosporine
aglycon.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1418
_journal_page_last 1421
_journal_paper_doi 10.1021/ol200094b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C27 H19 F N2 O6 S'
_chemical_formula_sum 'C27 H19 F N2 O6 S'
_chemical_formula_weight 518.50
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.216(6)
_cell_angle_beta 96.142(5)
_cell_angle_gamma 106.895(4)
_cell_formula_units_Z 2
_cell_length_a 8.2699(9)
_cell_length_b 11.0080(11)
_cell_length_c 13.4496(13)
_cell_measurement_reflns_used 1215
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 28.51
_cell_measurement_theta_min 1.52
_cell_volume 1164.0(2)
_computing_cell_refinement APEX2
_computing_data_collection 'APEX2 (Bruker, 2008)'
_computing_data_reduction 'SAINT (Bruker, 2008)'
_computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)'
_computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0379
_diffrn_reflns_av_sigmaI/netI 0.0459
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 21048
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 28.51
_diffrn_reflns_theta_min 1.52
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.196
_exptl_absorpt_correction_T_max 0.962
_exptl_absorpt_correction_T_min 0.952
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.479
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 536
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.2
_refine_diff_density_max 0.187
_refine_diff_density_min -0.330
_refine_diff_density_rms 0.039
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.020
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 336
_refine_ls_number_reflns 5780
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.020
_refine_ls_R_factor_all 0.0933
_refine_ls_R_factor_gt 0.0459
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.2055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1072
_refine_ls_wR_factor_ref 0.1267
_reflns_number_gt 3400
_reflns_number_total 5780
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200094b_si_001.cif
_cod_data_source_block compound-18e
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502025
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2678(2) 0.8670(2) 1.01904(14) 0.0479(5) Uani 1 1 d .
C2 C 0.2401(3) 0.7834(2) 1.09666(16) 0.0606(6) Uani 1 1 d .
H2 H 0.2609 0.7050 1.0929 0.073 Uiso 1 1 calc R
C3 C 0.1805(3) 0.8217(3) 1.17936(17) 0.0710(7) Uani 1 1 d .
H3 H 0.1590 0.7670 1.2321 0.085 Uiso 1 1 calc R
C4 C 0.1521(3) 0.9373(3) 1.18647(16) 0.0700(7) Uani 1 1 d .
H4 H 0.1099 0.9591 1.2432 0.084 Uiso 1 1 calc R
C5 C 0.1848(3) 1.0223(2) 1.11091(16) 0.0605(6) Uani 1 1 d .
H5 H 0.1690 1.1022 1.1171 0.073 Uiso 1 1 calc R
C6 C 0.2423(2) 0.9859(2) 1.02472(14) 0.0472(5) Uani 1 1 d .
C7 C 0.2810(2) 1.04755(19) 0.93088(14) 0.0429(4) Uani 1 1 d .
C8 C 0.3264(2) 0.96223(18) 0.87056(14) 0.0411(4) Uani 1 1 d .
C9 C 0.3660(2) 0.99012(18) 0.77465(14) 0.0426(4) Uani 1 1 d .
H9 H 0.4007 0.9339 0.7363 0.051 Uiso 1 1 calc R
C10 C 0.3527(2) 1.10387(18) 0.73713(14) 0.0420(4) Uani 1 1 d .
C11 C 0.3084(2) 1.19100(18) 0.79757(15) 0.0439(5) Uani 1 1 d .
C12 C 0.2765(2) 1.16586(19) 0.89599(14) 0.0453(5) Uani 1 1 d .
C13 C 0.2335(3) 1.2598(2) 0.96177(17) 0.0620(6) Uani 1 1 d .
H13A H 0.2421 1.3370 0.9270 0.093 Uiso 1 1 calc R
H13B H 0.3113 1.2774 1.0220 0.093 Uiso 1 1 calc R
H13C H 0.1195 1.2250 0.9785 0.093 Uiso 1 1 calc R
C14 C 0.2906(3) 1.3110(2) 0.75348(16) 0.0516(5) Uani 1 1 d .
C15 C 0.1330(4) 1.3952(3) 0.6309(2) 0.0970(10) Uani 1 1 d .
H15A H 0.1187 1.4555 0.6784 0.146 Uiso 1 1 calc R
H15B H 0.0328 1.3678 0.5836 0.146 Uiso 1 1 calc R
H15C H 0.2295 1.4342 0.5962 0.146 Uiso 1 1 calc R
C16 C 0.3947(2) 1.13759(19) 0.63407(14) 0.0439(5) Uani 1 1 d .
C17 C 0.5280(3) 1.2448(2) 0.62044(17) 0.0553(5) Uani 1 1 d .
H17 H 0.5892 1.2953 0.6754 0.066 Uiso 1 1 calc R
C18 C 0.5687(3) 1.2757(2) 0.5270(2) 0.0659(6) Uani 1 1 d .
C19 C 0.4858(3) 1.2062(3) 0.44291(19) 0.0702(7) Uani 1 1 d .
H19 H 0.5162 1.2311 0.3798 0.084 Uiso 1 1 calc R
C20 C 0.3560(3) 1.0981(3) 0.45433(17) 0.0646(6) Uani 1 1 d .
H20 H 0.2989 1.0467 0.3989 0.077 Uiso 1 1 calc R
C21 C 0.3112(2) 1.0664(2) 0.54865(15) 0.0480(5) Uani 1 1 d .
C22 C 0.0865(3) 0.66312(18) 0.81639(15) 0.0490(5) Uani 1 1 d .
C23 C 0.0448(3) 0.6964(2) 0.72070(17) 0.0647(6) Uani 1 1 d .
H23 H 0.1296 0.7398 0.6827 0.078 Uiso 1 1 calc R
C24 C -0.1237(3) 0.6650(3) 0.6816(2) 0.0817(8) Uani 1 1 d .
H24 H -0.1529 0.6883 0.6173 0.098 Uiso 1 1 calc R
C25 C -0.2482(3) 0.5997(2) 0.7371(2) 0.0746(7) Uani 1 1 d .
H25 H -0.3616 0.5785 0.7102 0.090 Uiso 1 1 calc R
C26 C -0.2069(3) 0.5654(2) 0.8314(2) 0.0679(7) Uani 1 1 d .
H26 H -0.2921 0.5202 0.8684 0.082 Uiso 1 1 calc R
C27 C -0.0391(3) 0.5976(2) 0.87212(17) 0.0599(6) Uani 1 1 d .
H27 H -0.0110 0.5751 0.9368 0.072 Uiso 1 1 calc R
N1 N 0.32510(19) 0.85133(15) 0.92459(11) 0.0457(4) Uani 1 1 d .
N2 N 0.1629(2) 0.95580(18) 0.55475(14) 0.0568(5) Uani 1 1 d .
O1 O 0.3794(2) 1.41500(16) 0.77780(15) 0.0858(6) Uani 1 1 d .
O2 O 0.16001(19) 1.28714(13) 0.68265(11) 0.0610(4) Uani 1 1 d .
O3 O 0.05957(19) 0.96330(16) 0.61027(12) 0.0664(4) Uani 1 1 d .
O4 O 0.1489(2) 0.86191(18) 0.50206(15) 0.0894(6) Uani 1 1 d .
O5 O 0.40657(19) 0.73408(14) 0.79160(11) 0.0614(4) Uani 1 1 d .
O6 O 0.3214(2) 0.62793(15) 0.94629(12) 0.0691(5) Uani 1 1 d .
S1 S 0.29945(7) 0.71058(5) 0.86920(4) 0.05154(17) Uani 1 1 d .
F1 F 0.6987(2) 1.38107(16) 0.51704(13) 0.1018(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0350(10) 0.0627(14) 0.0403(11) 0.0029(10) -0.0018(8) 0.0078(9)
C2 0.0531(12) 0.0780(17) 0.0459(13) 0.0138(12) 0.0014(10) 0.0129(12)
C3 0.0572(14) 0.104(2) 0.0456(14) 0.0196(13) 0.0034(11) 0.0142(14)
C4 0.0507(13) 0.114(2) 0.0387(12) 0.0000(14) 0.0030(10) 0.0137(14)
C5 0.0485(12) 0.0827(17) 0.0449(12) -0.0074(12) 0.0008(10) 0.0126(12)
C6 0.0324(9) 0.0668(14) 0.0374(11) -0.0026(10) -0.0009(8) 0.0084(9)
C7 0.0315(9) 0.0542(12) 0.0398(10) -0.0020(9) 0.0013(8) 0.0086(8)
C8 0.0319(9) 0.0464(12) 0.0419(11) 0.0015(9) 0.0009(8) 0.0078(8)
C9 0.0416(10) 0.0455(12) 0.0420(11) 0.0006(9) 0.0071(8) 0.0137(9)
C10 0.0349(9) 0.0439(11) 0.0441(11) 0.0000(9) 0.0035(8) 0.0072(8)
C11 0.0371(10) 0.0406(11) 0.0508(12) -0.0019(9) 0.0052(8) 0.0065(8)
C12 0.0342(9) 0.0512(12) 0.0474(12) -0.0067(9) 0.0022(8) 0.0086(9)
C13 0.0630(13) 0.0649(15) 0.0614(14) -0.0137(12) 0.0093(11) 0.0233(12)
C14 0.0497(12) 0.0436(13) 0.0600(14) -0.0020(10) 0.0133(10) 0.0088(10)
C15 0.137(3) 0.0621(18) 0.095(2) 0.0224(15) -0.0076(19) 0.0405(18)
C16 0.0445(10) 0.0467(12) 0.0444(11) 0.0058(9) 0.0076(9) 0.0187(9)
C17 0.0525(12) 0.0528(13) 0.0601(14) 0.0091(11) 0.0128(10) 0.0121(10)
C18 0.0619(14) 0.0687(16) 0.0711(17) 0.0246(13) 0.0238(13) 0.0194(13)
C19 0.0723(16) 0.097(2) 0.0563(15) 0.0280(15) 0.0277(13) 0.0409(16)
C20 0.0694(15) 0.0894(19) 0.0460(13) 0.0014(12) 0.0061(11) 0.0408(15)
C21 0.0459(11) 0.0535(13) 0.0486(12) 0.0029(10) 0.0035(9) 0.0216(10)
C22 0.0584(12) 0.0387(11) 0.0495(12) 0.0005(9) 0.0057(10) 0.0139(10)
C23 0.0663(15) 0.0602(15) 0.0573(14) 0.0113(12) 0.0019(11) 0.0042(12)
C24 0.0785(18) 0.0742(18) 0.0750(18) 0.0166(14) -0.0167(14) 0.0037(15)
C25 0.0614(15) 0.0555(15) 0.095(2) -0.0008(14) -0.0086(14) 0.0049(12)
C26 0.0617(15) 0.0536(15) 0.0802(18) -0.0044(13) 0.0137(13) 0.0020(12)
C27 0.0688(15) 0.0529(14) 0.0534(13) 0.0035(11) 0.0089(11) 0.0097(11)
N1 0.0434(9) 0.0513(10) 0.0405(9) 0.0058(8) 0.0029(7) 0.0114(8)
N2 0.0564(11) 0.0575(12) 0.0556(11) -0.0020(10) -0.0087(9) 0.0204(10)
O1 0.0888(13) 0.0427(10) 0.1105(15) -0.0033(10) -0.0027(11) 0.0003(9)
O2 0.0696(10) 0.0448(9) 0.0663(10) 0.0098(7) -0.0016(8) 0.0166(8)
O3 0.0506(9) 0.0759(11) 0.0690(11) 0.0058(9) 0.0052(8) 0.0134(8)
O4 0.0967(14) 0.0704(12) 0.0967(14) -0.0297(11) -0.0066(11) 0.0239(11)
O5 0.0642(9) 0.0609(10) 0.0694(10) 0.0099(8) 0.0237(8) 0.0285(8)
O6 0.0796(11) 0.0646(10) 0.0699(10) 0.0233(8) 0.0049(8) 0.0329(9)
S1 0.0549(3) 0.0505(3) 0.0536(3) 0.0105(2) 0.0079(2) 0.0215(3)
F1 0.0979(11) 0.0901(11) 0.1104(13) 0.0420(10) 0.0459(10) 0.0040(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 122.2(2)
C6 C1 N1 108.81(17)
C2 C1 N1 129.0(2)
C3 C2 C1 117.0(2)
C3 C2 H2 121.5
C1 C2 H2 121.5
C4 C3 C2 122.1(2)
C4 C3 H3 119.0
C2 C3 H3 119.0
C3 C4 C5 121.1(2)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 118.5(2)
C4 C5 H5 120.7
C6 C5 H5 120.7
C1 C6 C5 119.1(2)
C1 C6 C7 107.82(17)
C5 C6 C7 133.1(2)
C8 C7 C12 120.61(17)
C8 C7 C6 107.06(18)
C12 C7 C6 132.32(18)
C9 C8 C7 121.81(18)
C9 C8 N1 128.99(17)
C7 C8 N1 109.20(16)
C8 C9 C10 118.18(17)
C8 C9 H9 120.9
C10 C9 H9 120.9
C9 C10 C11 120.40(18)
C9 C10 C16 119.82(17)
C11 C10 C16 119.70(17)
C12 C11 C10 121.52(18)
C12 C11 C14 119.69(18)
C10 C11 C14 118.77(18)
C11 C12 C7 117.30(18)
C11 C12 C13 121.83(19)
C7 C12 C13 120.84(18)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O1 C14 O2 123.7(2)
O1 C14 C11 125.6(2)
O2 C14 C11 110.76(18)
O2 C15 H15A 109.5
O2 C15 H15B 109.5
H15A C15 H15B 109.5
O2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C21 C16 C17 116.55(19)
C21 C16 C10 124.06(18)
C17 C16 C10 119.37(18)
C18 C17 C16 119.9(2)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 F1 118.0(2)
C17 C18 C19 123.5(2)
F1 C18 C19 118.5(2)
C18 C19 C20 117.8(2)
C18 C19 H19 121.1
C20 C19 H19 121.1
C19 C20 C21 119.4(2)
C19 C20 H20 120.3
C21 C20 H20 120.3
C20 C21 C16 122.8(2)
C20 C21 N2 116.6(2)
C16 C21 N2 120.57(18)
C27 C22 C23 120.2(2)
C27 C22 S1 120.06(17)
C23 C22 S1 119.70(17)
C22 C23 C24 119.5(2)
C22 C23 H23 120.3
C24 C23 H23 120.3
C25 C24 C23 120.2(2)
C25 C24 H24 119.9
C23 C24 H24 119.9
C26 C25 C24 120.4(2)
C26 C25 H25 119.8
C24 C25 H25 119.8
C25 C26 C27 120.1(2)
C25 C26 H26 119.9
C27 C26 H26 119.9
C22 C27 C26 119.6(2)
C22 C27 H27 120.2
C26 C27 H27 120.2
C8 N1 C1 107.02(16)
C8 N1 S1 123.04(13)
C1 N1 S1 123.63(14)
O3 N2 O4 123.7(2)
O3 N2 C21 118.37(18)
O4 N2 C21 117.9(2)
C14 O2 C15 116.37(19)
O6 S1 O5 120.57(10)
O6 S1 N1 106.45(9)
O5 S1 N1 105.89(9)
O6 S1 C22 109.07(10)
O5 S1 C22 109.22(10)
N1 S1 C22 104.40(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.388(3)
C1 C2 1.388(3)
C1 N1 1.429(2)
C2 C3 1.376(3)
C2 H2 0.9300
C3 C4 1.365(4)
C3 H3 0.9300
C4 C5 1.379(3)
C4 H4 0.9300
C5 C6 1.398(3)
C5 H5 0.9300
C6 C7 1.457(3)
C7 C8 1.395(3)
C7 C12 1.395(3)
C8 C9 1.379(3)
C8 N1 1.421(2)
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.406(3)
C10 C16 1.487(3)
C11 C12 1.390(3)
C11 C14 1.490(3)
C12 C13 1.501(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 O1 1.189(2)
C14 O2 1.325(3)
C15 O2 1.441(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C21 1.385(3)
C16 C17 1.390(3)
C17 C18 1.355(3)
C17 H17 0.9300
C18 F1 1.352(3)
C18 C19 1.363(3)
C19 C20 1.373(3)
C19 H19 0.9300
C20 C21 1.377(3)
C20 H20 0.9300
C21 N2 1.466(3)
C22 C27 1.377(3)
C22 C23 1.375(3)
C22 S1 1.753(2)
C23 C24 1.379(3)
C23 H23 0.9300
C24 C25 1.368(4)
C24 H24 0.9300
C25 C26 1.361(3)
C25 H25 0.9300
C26 C27 1.379(3)
C26 H26 0.9300
C27 H27 0.9300
N1 S1 1.6635(17)
N2 O3 1.213(2)
N2 O4 1.221(2)
O5 S1 1.4170(15)
O6 S1 1.4137(15)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 2.0(3)
N1 C1 C2 C3 -178.55(19)
C1 C2 C3 C4 -1.1(3)
C2 C3 C4 C5 -1.1(4)
C3 C4 C5 C6 2.3(3)
C2 C1 C6 C5 -0.8(3)
N1 C1 C6 C5 179.66(16)
C2 C1 C6 C7 -179.37(17)
N1 C1 C6 C7 1.1(2)
C4 C5 C6 C1 -1.4(3)
C4 C5 C6 C7 176.8(2)
C1 C6 C7 C8 0.9(2)
C5 C6 C7 C8 -177.4(2)
C1 C6 C7 C12 179.68(19)
C5 C6 C7 C12 1.3(4)
C12 C7 C8 C9 -0.9(3)
C6 C7 C8 C9 178.01(16)
C12 C7 C8 N1 178.51(16)
C6 C7 C8 N1 -2.6(2)
C7 C8 C9 C10 -2.7(3)
N1 C8 C9 C10 177.98(17)
C8 C9 C10 C11 3.2(3)
C8 C9 C10 C16 179.85(16)
C9 C10 C11 C12 -0.1(3)
C16 C10 C11 C12 -176.76(16)
C9 C10 C11 C14 -178.33(17)
C16 C10 C11 C14 5.0(3)
C10 C11 C12 C7 -3.5(3)
C14 C11 C12 C7 174.75(17)
C10 C11 C12 C13 178.41(18)
C14 C11 C12 C13 -3.4(3)
C8 C7 C12 C11 3.9(3)
C6 C7 C12 C11 -174.66(18)
C8 C7 C12 C13 -177.91(17)
C6 C7 C12 C13 3.5(3)
C12 C11 C14 O1 67.6(3)
C10 C11 C14 O1 -114.2(3)
C12 C11 C14 O2 -112.0(2)
C10 C11 C14 O2 66.3(2)
C9 C10 C16 C21 60.4(3)
C11 C10 C16 C21 -122.9(2)
C9 C10 C16 C17 -117.9(2)
C11 C10 C16 C17 58.8(2)
C21 C16 C17 C18 0.8(3)
C10 C16 C17 C18 179.25(19)
C16 C17 C18 F1 179.74(19)
C16 C17 C18 C19 -0.4(4)
C17 C18 C19 C20 -1.0(4)
F1 C18 C19 C20 178.8(2)
C18 C19 C20 C21 2.0(3)
C19 C20 C21 C16 -1.7(3)
C19 C20 C21 N2 175.16(19)
C17 C16 C21 C20 0.2(3)
C10 C16 C21 C20 -178.12(18)
C17 C16 C21 N2 -176.50(17)
C10 C16 C21 N2 5.2(3)
C27 C22 C23 C24 0.8(4)
S1 C22 C23 C24 -176.4(2)
C22 C23 C24 C25 -0.9(4)
C23 C24 C25 C26 0.2(4)
C24 C25 C26 C27 0.7(4)
C23 C22 C27 C26 0.1(3)
S1 C22 C27 C26 177.23(17)
C25 C26 C27 C22 -0.8(4)
C9 C8 N1 C1 -177.42(18)
C7 C8 N1 C1 3.2(2)
C9 C8 N1 S1 -24.6(3)
C7 C8 N1 S1 156.07(13)
C6 C1 N1 C8 -2.6(2)
C2 C1 N1 C8 177.86(19)
C6 C1 N1 S1 -155.26(13)
C2 C1 N1 S1 25.2(3)
C20 C21 N2 O3 -136.2(2)
C16 C21 N2 O3 40.7(3)
C20 C21 N2 O4 42.5(3)
C16 C21 N2 O4 -140.6(2)
O1 C14 O2 C15 2.9(3)
C11 C14 O2 C15 -177.5(2)
C8 N1 S1 O6 174.59(14)
C1 N1 S1 O6 -37.00(17)
C8 N1 S1 O5 45.15(16)
C1 N1 S1 O5 -166.45(14)
C8 N1 S1 C22 -70.09(16)
C1 N1 S1 C22 78.31(16)
C27 C22 S1 O6 25.9(2)
C23 C22 S1 O6 -156.95(18)
C27 C22 S1 O5 159.54(17)
C23 C22 S1 O5 -23.3(2)
C27 C22 S1 N1 -87.59(18)
C23 C22 S1 N1 89.60(19)
|
1502026.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502026.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502026
loop_
_publ_author_name
'Rajeshwaran, Ganesan Gobi'
'Mohanakrishnan, Arasambattu K.'
_publ_section_title
;
Synthetic studies on indolocarbazoles: total synthesis of staurosporine
aglycon.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1418
_journal_page_last 1421
_journal_paper_doi 10.1021/ol200094b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C28 H20 N2 O8 S'
_chemical_formula_sum 'C28 H20 N2 O8 S'
_chemical_formula_weight 544.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 65.376(2)
_cell_angle_beta 76.518(2)
_cell_angle_gamma 70.244(2)
_cell_formula_units_Z 2
_cell_length_a 8.6850(3)
_cell_length_b 12.5559(4)
_cell_length_c 13.1495(4)
_cell_measurement_reflns_used 1235
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 0.963
_cell_measurement_theta_min 0.952
_cell_volume 1219.64(7)
_computing_cell_refinement APEX2
_computing_data_collection 'APEX2 (Bruker, 2008)'
_computing_data_reduction 'SAINT (Bruker, 2008)'
_computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)'
_computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method '\w and \f scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0266
_diffrn_reflns_av_sigmaI/netI 0.0267
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 22408
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 28.34
_diffrn_reflns_theta_min 1.71
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.191
_exptl_absorpt_correction_T_max 28.34
_exptl_absorpt_correction_T_min 1.71
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Bruker, 2008)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.483
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 564
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.2
_refine_diff_density_max 0.286
_refine_diff_density_min -0.371
_refine_diff_density_rms 0.040
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 354
_refine_ls_number_reflns 6080
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.041
_refine_ls_R_factor_all 0.0589
_refine_ls_R_factor_gt 0.0409
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.2816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1096
_refine_ls_wR_factor_ref 0.1215
_reflns_number_gt 4555
_reflns_number_total 6080
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200094b_si_001.cif
_cod_data_source_block compound-18f
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502026
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.1411(2) 0.14130(14) 0.49188(13) 0.0390(3) Uani 1 1 d .
C2 C -0.1954(2) 0.10791(16) 0.60559(14) 0.0473(4) Uani 1 1 d .
H2 H -0.1321 0.1016 0.6570 0.057 Uiso 1 1 calc R
C3 C -0.3473(2) 0.08438(17) 0.63969(15) 0.0530(4) Uani 1 1 d .
H3 H -0.3872 0.0624 0.7155 0.064 Uiso 1 1 calc R
C4 C -0.4415(2) 0.09278(17) 0.56376(16) 0.0528(4) Uani 1 1 d .
H4 H -0.5446 0.0785 0.5891 0.063 Uiso 1 1 calc R
C5 C -0.3848(2) 0.12193(16) 0.45120(15) 0.0474(4) Uani 1 1 d .
H5 H -0.4476 0.1253 0.4010 0.057 Uiso 1 1 calc R
C6 C -0.23148(19) 0.14639(14) 0.41362(13) 0.0382(3) Uani 1 1 d .
C7 C -0.13642(18) 0.17971(14) 0.30381(13) 0.0367(3) Uani 1 1 d .
C8 C 0.00626(19) 0.19851(14) 0.31856(13) 0.0371(3) Uani 1 1 d .
C9 C -0.0562(2) 0.39134(16) 0.44764(14) 0.0433(4) Uani 1 1 d .
C10 C -0.0477(2) 0.47935(18) 0.34077(16) 0.0541(4) Uani 1 1 d .
H10 H 0.0381 0.4649 0.2865 0.065 Uiso 1 1 calc R
C11 C -0.1673(3) 0.5881(2) 0.31593(19) 0.0668(6) Uani 1 1 d .
H11 H -0.1626 0.6479 0.2444 0.080 Uiso 1 1 calc R
C12 C -0.2934(3) 0.6093(2) 0.3954(2) 0.0702(6) Uani 1 1 d .
H12 H -0.3739 0.6834 0.3776 0.084 Uiso 1 1 calc R
C13 C -0.3022(3) 0.5222(2) 0.5014(2) 0.0705(6) Uani 1 1 d .
H13 H -0.3888 0.5374 0.5549 0.085 Uiso 1 1 calc R
C14 C -0.1828(3) 0.41174(19) 0.52895(16) 0.0562(5) Uani 1 1 d .
H14 H -0.1877 0.3524 0.6008 0.067 Uiso 1 1 calc R
C15 C 0.12414(19) 0.23146(15) 0.23052(13) 0.0413(4) Uani 1 1 d .
H15 H 0.2185 0.2423 0.2421 0.050 Uiso 1 1 calc R
C16 C 0.09841(19) 0.24795(14) 0.12441(13) 0.0388(3) Uani 1 1 d .
C17 C -0.0433(2) 0.22901(14) 0.10813(13) 0.0387(3) Uani 1 1 d .
C18 C -0.16066(19) 0.19215(14) 0.19717(13) 0.0387(3) Uani 1 1 d .
C19 C -0.3091(2) 0.16710(19) 0.18022(15) 0.0524(4) Uani 1 1 d .
H19A H -0.3142 0.1918 0.1012 0.079 Uiso 1 1 calc R
H19B H -0.4070 0.2120 0.2119 0.079 Uiso 1 1 calc R
H19C H -0.3005 0.0816 0.2167 0.079 Uiso 1 1 calc R
C20 C -0.0679(2) 0.25331(15) -0.00924(14) 0.0418(4) Uani 1 1 d .
C21 C -0.0585(3) 0.1620(2) -0.13751(16) 0.0623(5) Uani 1 1 d .
H22A H -0.1613 0.2193 -0.1613 0.093 Uiso 1 1 calc R
H22B H -0.0554 0.0839 -0.1352 0.093 Uiso 1 1 calc R
H22C H 0.0304 0.1896 -0.1896 0.093 Uiso 1 1 calc R
C22 C 0.2267(2) 0.28565(15) 0.02979(13) 0.0399(3) Uani 1 1 d .
C23 C 0.2490(2) 0.40077(16) 0.00077(15) 0.0470(4) Uani 1 1 d .
H24 H 0.1834 0.4526 0.0376 0.056 Uiso 1 1 calc R
C24 C 0.3694(2) 0.43470(16) -0.08275(15) 0.0484(4) Uani 1 1 d .
C25 C 0.4664(2) 0.36101(17) -0.14065(14) 0.0472(4) Uani 1 1 d .
C26 C 0.4486(2) 0.24960(16) -0.11670(14) 0.0477(4) Uani 1 1 d .
H27 H 0.5131 0.2001 -0.1560 0.057 Uiso 1 1 calc R
C27 C 0.3278(2) 0.21348(15) -0.02960(14) 0.0408(3) Uani 1 1 d .
C28 C 0.5478(3) 0.5300(2) -0.2065(2) 0.0770(7) Uani 1 1 d .
H29A H 0.6458 0.5299 -0.1830 0.092 Uiso 1 1 calc R
H29B H 0.5249 0.5984 -0.2768 0.092 Uiso 1 1 calc R
N1 N 0.00818(16) 0.17207(12) 0.43445(11) 0.0404(3) Uani 1 1 d .
N2 N 0.31534(18) 0.09055(14) -0.00076(14) 0.0491(4) Uani 1 1 d .
O1 O 0.09402(17) 0.18731(13) 0.59422(10) 0.0582(3) Uani 1 1 d .
O2 O 0.23634(15) 0.26284(13) 0.40377(11) 0.0555(3) Uani 1 1 d .
O3 O -0.1017(2) 0.35315(12) -0.08065(11) 0.0659(4) Uani 1 1 d .
O4 O -0.04187(17) 0.15176(12) -0.02627(10) 0.0550(3) Uani 1 1 d .
O5 O 0.27778(17) 0.03123(12) 0.09731(12) 0.0604(3) Uani 1 1 d .
O6 O 0.34714(19) 0.05222(14) -0.07709(14) 0.0703(4) Uani 1 1 d .
O7 O 0.57348(17) 0.41890(13) -0.22147(12) 0.0647(4) Uani 1 1 d .
O8 O 0.41297(19) 0.54085(13) -0.12334(13) 0.0690(4) Uani 1 1 d .
S1 S 0.08912(5) 0.24901(4) 0.47617(3) 0.04401(12) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0422(8) 0.0330(8) 0.0388(8) -0.0122(6) -0.0060(6) -0.0067(6)
C2 0.0576(11) 0.0435(9) 0.0375(9) -0.0129(7) -0.0067(7) -0.0114(8)
C3 0.0628(12) 0.0476(10) 0.0406(9) -0.0135(8) 0.0040(8) -0.0152(9)
C4 0.0501(10) 0.0522(11) 0.0524(11) -0.0178(8) 0.0046(8) -0.0183(8)
C5 0.0447(9) 0.0493(10) 0.0487(10) -0.0176(8) -0.0028(7) -0.0156(8)
C6 0.0409(8) 0.0324(8) 0.0378(8) -0.0113(6) -0.0045(6) -0.0075(6)
C7 0.0376(8) 0.0332(8) 0.0378(8) -0.0124(6) -0.0048(6) -0.0084(6)
C8 0.0392(8) 0.0355(8) 0.0367(8) -0.0145(6) -0.0067(6) -0.0070(6)
C9 0.0462(9) 0.0483(10) 0.0431(9) -0.0202(7) -0.0074(7) -0.0160(7)
C10 0.0541(11) 0.0580(12) 0.0458(10) -0.0134(8) -0.0015(8) -0.0197(9)
C11 0.0731(14) 0.0544(12) 0.0613(13) -0.0059(10) -0.0144(11) -0.0181(11)
C12 0.0711(14) 0.0546(13) 0.0820(16) -0.0276(12) -0.0192(12) -0.0034(11)
C13 0.0675(14) 0.0719(15) 0.0699(14) -0.0389(12) 0.0007(11) -0.0056(11)
C14 0.0668(12) 0.0566(12) 0.0435(10) -0.0217(8) 0.0015(8) -0.0157(10)
C15 0.0387(8) 0.0469(9) 0.0435(9) -0.0203(7) -0.0043(7) -0.0136(7)
C16 0.0404(8) 0.0371(8) 0.0395(8) -0.0165(7) -0.0013(6) -0.0104(7)
C17 0.0444(8) 0.0355(8) 0.0374(8) -0.0143(6) -0.0073(6) -0.0094(7)
C18 0.0408(8) 0.0368(8) 0.0400(8) -0.0141(6) -0.0082(6) -0.0099(7)
C19 0.0530(10) 0.0679(12) 0.0474(10) -0.0231(9) -0.0047(8) -0.0281(9)
C20 0.0433(9) 0.0439(9) 0.0396(8) -0.0158(7) -0.0049(7) -0.0130(7)
C21 0.0866(15) 0.0654(13) 0.0486(11) -0.0269(9) -0.0163(10) -0.0240(11)
C22 0.0411(8) 0.0416(9) 0.0390(8) -0.0164(7) -0.0039(6) -0.0120(7)
C23 0.0511(10) 0.0430(9) 0.0496(10) -0.0233(8) 0.0035(8) -0.0140(8)
C24 0.0504(10) 0.0399(9) 0.0525(10) -0.0145(8) -0.0034(8) -0.0143(8)
C25 0.0430(9) 0.0507(10) 0.0405(9) -0.0114(7) 0.0002(7) -0.0137(8)
C26 0.0451(9) 0.0490(10) 0.0456(9) -0.0215(8) -0.0001(7) -0.0068(8)
C27 0.0413(8) 0.0383(8) 0.0434(9) -0.0165(7) -0.0057(7) -0.0092(7)
C28 0.0776(15) 0.0643(14) 0.0805(16) -0.0198(12) 0.0183(12) -0.0356(12)
N1 0.0429(7) 0.0440(8) 0.0356(7) -0.0154(6) -0.0071(5) -0.0108(6)
N2 0.0418(8) 0.0452(8) 0.0644(10) -0.0277(8) -0.0063(7) -0.0068(6)
O1 0.0674(8) 0.0678(9) 0.0416(7) -0.0153(6) -0.0213(6) -0.0170(7)
O2 0.0395(7) 0.0779(9) 0.0590(8) -0.0327(7) -0.0073(6) -0.0172(6)
O3 0.1018(11) 0.0467(8) 0.0447(7) -0.0101(6) -0.0199(7) -0.0153(7)
O4 0.0799(9) 0.0477(7) 0.0439(7) -0.0194(5) -0.0174(6) -0.0149(6)
O5 0.0643(9) 0.0422(7) 0.0656(9) -0.0108(6) -0.0072(7) -0.0148(6)
O6 0.0719(10) 0.0729(10) 0.0887(11) -0.0556(9) 0.0046(8) -0.0228(8)
O7 0.0610(8) 0.0613(9) 0.0611(9) -0.0179(7) 0.0167(7) -0.0252(7)
O8 0.0744(10) 0.0483(8) 0.0794(10) -0.0217(7) 0.0169(8) -0.0300(7)
S1 0.0430(2) 0.0531(3) 0.0404(2) -0.01865(19) -0.01170(16) -0.01193(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 122.19(15)
C2 C1 N1 128.88(15)
C6 C1 N1 108.91(13)
C3 C2 C1 117.40(17)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 121.55(17)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 120.99(17)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 119.01(17)
C4 C5 H5 120.5
C6 C5 H5 120.5
C5 C6 C1 118.77(15)
C5 C6 C7 133.55(15)
C1 C6 C7 107.68(14)
C18 C7 C8 120.04(14)
C18 C7 C6 133.04(14)
C8 C7 C6 106.91(13)
C15 C8 C7 122.09(14)
C15 C8 N1 128.41(14)
C7 C8 N1 109.42(13)
C14 C9 C10 121.01(18)
C14 C9 S1 119.99(14)
C10 C9 S1 118.87(14)
C11 C10 C9 119.09(19)
C11 C10 H10 120.5
C9 C10 H10 120.5
C12 C11 C10 120.5(2)
C12 C11 H11 119.8
C10 C11 H11 119.8
C11 C12 C13 120.5(2)
C11 C12 H12 119.7
C13 C12 H12 119.7
C12 C13 C14 120.2(2)
C12 C13 H13 119.9
C14 C13 H13 119.9
C9 C14 C13 118.66(19)
C9 C14 H14 120.7
C13 C14 H14 120.7
C8 C15 C16 118.20(14)
C8 C15 H15 120.9
C16 C15 H15 120.9
C15 C16 C17 120.50(14)
C15 C16 C22 117.28(14)
C17 C16 C22 122.22(14)
C18 C17 C16 121.70(14)
C18 C17 C20 120.22(14)
C16 C17 C20 118.05(14)
C17 C18 C7 117.40(14)
C17 C18 C19 121.58(14)
C7 C18 C19 121.02(14)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
O3 C20 O4 123.91(16)
O3 C20 C17 123.91(15)
O4 C20 C17 112.14(14)
O4 C21 H22A 109.5
O4 C21 H22B 109.5
H22A C21 H22B 109.5
O4 C21 H22C 109.5
H22A C21 H22C 109.5
H22B C21 H22C 109.5
C27 C22 C23 117.85(15)
C27 C22 C16 124.56(14)
C23 C22 C16 117.57(14)
C24 C23 C22 118.24(15)
C24 C23 H24 120.9
C22 C23 H24 120.9
C23 C24 O8 127.99(16)
C23 C24 C25 122.24(16)
O8 C24 C25 109.76(15)
C26 C25 O7 128.35(16)
C26 C25 C24 121.82(16)
O7 C25 C24 109.82(16)
C25 C26 C27 116.08(15)
C25 C26 H27 122.0
C27 C26 H27 122.0
C22 C27 C26 123.74(15)
C22 C27 N2 120.66(15)
C26 C27 N2 115.58(14)
O8 C28 O7 108.49(16)
O8 C28 H29A 110.0
O7 C28 H29A 110.0
O8 C28 H29B 110.0
O7 C28 H29B 110.0
H29A C28 H29B 108.4
C8 N1 C1 107.00(12)
C8 N1 S1 121.46(11)
C1 N1 S1 120.42(10)
O5 N2 O6 123.73(16)
O5 N2 C27 118.85(14)
O6 N2 C27 117.40(16)
C20 O4 C21 117.94(14)
C25 O7 C28 105.47(14)
C24 O8 C28 106.13(15)
O2 S1 O1 120.29(8)
O2 S1 N1 106.28(7)
O1 S1 N1 106.35(8)
O2 S1 C9 109.16(8)
O1 S1 C9 109.93(8)
N1 S1 C9 103.41(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(2)
C1 C6 1.403(2)
C1 N1 1.428(2)
C2 C3 1.380(3)
C2 H2 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.377(2)
C4 H4 0.9300
C5 C6 1.398(2)
C5 H5 0.9300
C6 C7 1.455(2)
C7 C18 1.403(2)
C7 C8 1.406(2)
C8 C15 1.376(2)
C8 N1 1.4210(19)
C9 C14 1.381(2)
C9 C10 1.384(2)
C9 S1 1.7506(18)
C10 C11 1.370(3)
C10 H10 0.9300
C11 C12 1.365(3)
C11 H11 0.9300
C12 C13 1.371(3)
C12 H12 0.9300
C13 C14 1.383(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.383(2)
C15 H15 0.9300
C16 C17 1.407(2)
C16 C22 1.494(2)
C17 C18 1.391(2)
C17 C20 1.496(2)
C18 C19 1.509(2)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 O3 1.199(2)
C20 O4 1.322(2)
C21 O4 1.451(2)
C21 H22A 0.9600
C21 H22B 0.9600
C21 H22C 0.9600
C22 C27 1.391(2)
C22 C23 1.403(2)
C23 C24 1.363(2)
C23 H24 0.9300
C24 O8 1.363(2)
C24 C25 1.381(2)
C25 C26 1.355(2)
C25 O7 1.370(2)
C26 C27 1.395(2)
C26 H27 0.9300
C27 N2 1.464(2)
C28 O8 1.416(3)
C28 O7 1.426(3)
C28 H29A 0.9700
C28 H29B 0.9700
N1 S1 1.6759(13)
N2 O5 1.221(2)
N2 O6 1.2242(19)
O1 S1 1.4206(13)
O2 S1 1.4199(13)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -2.8(2)
N1 C1 C2 C3 178.99(16)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 1.8(3)
C3 C4 C5 C6 -1.7(3)
C4 C5 C6 C1 -0.5(2)
C4 C5 C6 C7 -179.69(17)
C2 C1 C6 C5 2.8(2)
N1 C1 C6 C5 -178.65(14)
C2 C1 C6 C7 -177.82(14)
N1 C1 C6 C7 0.74(17)
C5 C6 C7 C18 -4.5(3)
C1 C6 C7 C18 176.24(17)
C5 C6 C7 C8 176.97(17)
C1 C6 C7 C8 -2.29(17)
C18 C7 C8 C15 1.2(2)
C6 C7 C8 C15 180.00(14)
C18 C7 C8 N1 -175.76(13)
C6 C7 C8 N1 3.00(17)
C14 C9 C10 C11 -0.1(3)
S1 C9 C10 C11 175.82(15)
C9 C10 C11 C12 -0.1(3)
C10 C11 C12 C13 0.1(4)
C11 C12 C13 C14 0.2(4)
C10 C9 C14 C13 0.3(3)
S1 C9 C14 C13 -175.52(16)
C12 C13 C14 C9 -0.4(3)
C7 C8 C15 C16 1.0(2)
N1 C8 C15 C16 177.34(15)
C8 C15 C16 C17 -1.2(2)
C8 C15 C16 C22 179.04(14)
C15 C16 C17 C18 -0.7(2)
C22 C16 C17 C18 179.02(15)
C15 C16 C17 C20 177.48(15)
C22 C16 C17 C20 -2.8(2)
C16 C17 C18 C7 2.8(2)
C20 C17 C18 C7 -175.32(14)
C16 C17 C18 C19 -177.54(16)
C20 C17 C18 C19 4.3(2)
C8 C7 C18 C17 -3.1(2)
C6 C7 C18 C17 178.56(16)
C8 C7 C18 C19 177.30(15)
C6 C7 C18 C19 -1.1(3)
C18 C17 C20 O3 107.6(2)
C16 C17 C20 O3 -70.6(2)
C18 C17 C20 O4 -74.78(19)
C16 C17 C20 O4 107.01(17)
C15 C16 C22 C27 112.98(18)
C17 C16 C22 C27 -66.8(2)
C15 C16 C22 C23 -65.4(2)
C17 C16 C22 C23 114.83(18)
C27 C22 C23 C24 -0.8(3)
C16 C22 C23 C24 177.75(16)
C22 C23 C24 O8 -179.35(18)
C22 C23 C24 C25 1.5(3)
C23 C24 C25 C26 -0.8(3)
O8 C24 C25 C26 179.87(17)
C23 C24 C25 O7 178.36(17)
O8 C24 C25 O7 -0.9(2)
O7 C25 C26 C27 -179.58(17)
C24 C25 C26 C27 -0.5(3)
C23 C22 C27 C26 -0.6(3)
C16 C22 C27 C26 -179.04(16)
C23 C22 C27 N2 177.65(15)
C16 C22 C27 N2 -0.8(2)
C25 C26 C27 C22 1.3(3)
C25 C26 C27 N2 -177.08(16)
C15 C8 N1 C1 -179.31(15)
C7 C8 N1 C1 -2.56(16)
C15 C8 N1 S1 36.8(2)
C7 C8 N1 S1 -146.44(12)
C2 C1 N1 C8 179.52(16)
C6 C1 N1 C8 1.08(16)
C2 C1 N1 S1 -36.2(2)
C6 C1 N1 S1 145.41(12)
C22 C27 N2 O5 -32.5(2)
C26 C27 N2 O5 145.88(16)
C22 C27 N2 O6 149.04(16)
C26 C27 N2 O6 -32.5(2)
O3 C20 O4 C21 -1.3(3)
C17 C20 O4 C21 -178.86(15)
C26 C25 O7 C28 -176.7(2)
C24 C25 O7 C28 4.1(2)
O8 C28 O7 C25 -5.8(3)
C23 C24 O8 C28 178.0(2)
C25 C24 O8 C28 -2.7(2)
O7 C28 O8 C24 5.3(3)
C8 N1 S1 O2 -41.76(14)
C1 N1 S1 O2 179.06(12)
C8 N1 S1 O1 -171.06(12)
C1 N1 S1 O1 49.76(14)
C8 N1 S1 C9 73.14(13)
C1 N1 S1 C9 -66.04(13)
C14 C9 S1 O2 -156.64(14)
C10 C9 S1 O2 27.41(16)
C14 C9 S1 O1 -22.69(17)
C10 C9 S1 O1 161.36(14)
C14 C9 S1 N1 90.54(15)
C10 C9 S1 N1 -85.42(15)
|
1502027.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502027.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502027
loop_
_publ_author_name
'Lin, Hongkun'
'Pochapsky, Susan S.'
'Krauss, Isaac J.'
_publ_section_title
;
A short asymmetric route to the bromophycolide A and D skeleton.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1222
_journal_page_last 1225
_journal_paper_doi 10.1021/ol200099n
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C29 H41 Br1 O4'
_chemical_formula_sum 'C29 H41 Br O4'
_chemical_formula_weight 533.55
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_audit_creation_date 09-09-22
_audit_creation_method CRYSTALS_ver_12.87
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 8.4428(6)
_cell_length_b 10.0656(7)
_cell_length_c 32.412(2)
_cell_measurement_reflns_used 8273
_cell_measurement_temperature 120
_cell_measurement_theta_max 25
_cell_measurement_theta_min 2
_cell_volume 2754.4(3)
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature 120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'Bruker Kappa Apex2'
_diffrn_measurement_device_type Area
_diffrn_measurement_method '\f & \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.057
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -41
_diffrn_reflns_number 40366
_diffrn_reflns_theta_full 27.028
_diffrn_reflns_theta_max 27.028
_diffrn_reflns_theta_min 1.256
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 1.523
_exptl_absorpt_correction_T_max 0.83
_exptl_absorpt_correction_T_min 0.79
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.287
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description 'acicular fragment'
_exptl_crystal_F_000 1128
_exptl_crystal_size_max 0.399
_exptl_crystal_size_mid 0.154
_exptl_crystal_size_min 0.126
_refine_diff_density_max 0.52
_refine_diff_density_min -0.63
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack 0.000(6)
_refine_ls_extinction_method None
_refine_ls_goodness_of_fit_ref 0.9653
_refine_ls_hydrogen_treatment none
_refine_ls_matrix_type full
_refine_ls_number_parameters 328
_refine_ls_number_reflns 6023
_refine_ls_number_restraints 13
_refine_ls_R_factor_all 0.0427
_refine_ls_R_factor_gt 0.0331
_refine_ls_shift/su_max 0.0135880
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.89P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_all 0.0673
_refine_ls_wR_factor_gt 0.0657
_refine_ls_wR_factor_ref 0.0673
_reflns_limit_h_max 10
_reflns_limit_h_min -10
_reflns_limit_k_max 12
_reflns_limit_k_min 0
_reflns_limit_l_max 41
_reflns_limit_l_min 0
_reflns_number_gt 5179
_reflns_number_total 6023
_reflns_threshold_expression I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor 2.10
_oxford_diffrn_Wilson_scale 3.78
_oxford_refine_ls_r_factor_ref 0.0427
_oxford_refine_ls_scale 0.18838(8)
_oxford_reflns_number_all 6023
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'LHK1_101_1_0m in P2(1)2(1)2(1)'
_cod_data_source_file ol200099n_si_001.cif
_cod_data_source_block global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M 'P 21 21 21 '
_cod_original_formula_sum 'C29 H41 Br1 O4'
_cod_database_code 1502027
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.17412(4) 0.80266(4) 0.294118(10) 0.0317 0.7809(14) Uani D . P 1 3
Br2 Br 0.8560(4) 0.8698(3) 0.25399(10) 0.0332 0.1665(14) Uani D . P 1 5
Br3 Br 1.0724(7) 1.1002(5) 0.29087(17) 0.0446(18) 0.0526(12) Uiso D U P 1 2
O1 O 0.85064(16) 0.77947(13) 0.34474(4) 0.0211 1.0000 Uani . . . . .
O2 O 0.60406(18) 0.86263(15) 0.35233(5) 0.0280 1.0000 Uani . . . . .
O3 O 0.43411(18) 0.25715(14) 0.33183(5) 0.0227 1.0000 Uani . . . . .
O4 O 0.60632(18) 0.13587(15) 0.28890(5) 0.0257 1.0000 Uani . . . . .
C1 C 0.6913(3) 0.76910(19) 0.34855(6) 0.0199 1.0000 Uani . . . . .
C2 C 0.6361(2) 0.6292(2) 0.34658(6) 0.0186 1.0000 Uani . . . . .
C3 C 0.7315(3) 0.5252(2) 0.33301(7) 0.0230 1.0000 Uani . . . . .
C4 C 0.6672(3) 0.3999(2) 0.32792(6) 0.0233 1.0000 Uani . . . . .
C5 C 0.5085(3) 0.3776(2) 0.33713(6) 0.0194 1.0000 Uani . . . . .
C6 C 0.4120(2) 0.4795(2) 0.35264(6) 0.0180 1.0000 Uani . . . . .
C7 C 0.4783(3) 0.6042(2) 0.35655(6) 0.0193 1.0000 Uani . . . . .
C8 C 0.5304(3) 0.1413(2) 0.32696(7) 0.0239 1.0000 Uani . . . . .
C9 C 0.5004(3) 0.1126(3) 0.25551(8) 0.0383 1.0000 Uani . . . . .
C10 C 0.2408(3) 0.4520(2) 0.36401(7) 0.0239 1.0000 Uani . . . . .
C11 C 0.1720(3) 0.54671(19) 0.39567(6) 0.0203 1.0000 Uani . . . . .
C12 C 0.2171(2) 0.5545(2) 0.43482(6) 0.0197 1.0000 Uani . . . . .
C13 C 0.3444(3) 0.4675(3) 0.45254(7) 0.0393 1.0000 Uani . . . . .
C14 C 0.1413(3) 0.6492(2) 0.46491(6) 0.0222 1.0000 Uani . . . . .
C15 C 0.2551(3) 0.7479(2) 0.48547(7) 0.0259 1.0000 Uani . . . . .
C16 C 0.3170(3) 0.8525(2) 0.45631(6) 0.0202 1.0000 Uani . . . . .
C17 C 0.3261(3) 0.9823(2) 0.46287(6) 0.0206 1.0000 Uani . . . . .
C18 C 0.2806(3) 1.0487(2) 0.50276(7) 0.0335 1.0000 Uani . . . . .
C19 C 0.3800(3) 1.0765(2) 0.42948(7) 0.0233 1.0000 Uani . . . . .
C20 C 0.5416(2) 1.1416(2) 0.43780(7) 0.0235 1.0000 Uani . . . . .
C21 C 0.6735(3) 1.0439(2) 0.43262(6) 0.0208 1.0000 Uani . . . . .
C22 C 0.8225(3) 1.0654(2) 0.42122(6) 0.0212 1.0000 Uani . . . . .
C23 C 0.8898(3) 1.2007(3) 0.41220(8) 0.0327 1.0000 Uani . . . . .
C24 C 0.9362(3) 0.9501(2) 0.41791(7) 0.0258 1.0000 Uani . . . . .
C25 C 1.0245(3) 0.9376(2) 0.37696(6) 0.0236 1.0000 Uani . . . . .
C26 C 0.9147(2) 0.9117(2) 0.34003(6) 0.0196 1.0000 Uani D . . . .
C27 C 0.9972(2) 0.92176(19) 0.29788(6) 0.0268 1.0000 Uani D U . . .
C28 C 1.0544(5) 1.0630(3) 0.29016(11) 0.0411 0.9474(12) Uani . . P 1 1
C29 C 1.1414(8) 0.8267(7) 0.29775(15) 0.044(4) 0.2191(14) Uiso D U P 1 4
C30 C 0.8787(7) 0.8879(5) 0.26305(19) 0.0488 0.8335(14) Uani D . P 1 7
H31 H 0.8412 0.5414 0.3268 0.0282 1.0000 Uiso R . . . .
H41 H 0.7329 0.3296 0.3179 0.0305 1.0000 Uiso R . . . .
H71 H 0.4164 0.6765 0.3663 0.0237 1.0000 Uiso R . . . .
H81 H 0.4604 0.0662 0.3294 0.0294 1.0000 Uiso R . . . .
H82 H 0.6137 0.1407 0.3487 0.0294 1.0000 Uiso R . . . .
H91 H 0.5672 0.0970 0.2318 0.0589 1.0000 Uiso R . . . .
H92 H 0.4283 0.0366 0.2622 0.0597 1.0000 Uiso R . . . .
H93 H 0.4381 0.1926 0.2523 0.0609 1.0000 Uiso R . . . .
H101 H 0.1769 0.4558 0.3392 0.0307 1.0000 Uiso R . . . .
H102 H 0.2340 0.3640 0.3756 0.0299 1.0000 Uiso R . . . .
H111 H 0.0890 0.6036 0.3866 0.0256 1.0000 Uiso R . . . .
H131 H 0.3590 0.3871 0.4363 0.0609 1.0000 Uiso R . . . .
H132 H 0.4418 0.5183 0.4531 0.0623 1.0000 Uiso R . . . .
H133 H 0.3161 0.4456 0.4810 0.0609 1.0000 Uiso R . . . .
H141 H 0.0543 0.6976 0.4500 0.0273 1.0000 Uiso R . . . .
H142 H 0.0917 0.5957 0.4869 0.0278 1.0000 Uiso R . . . .
H151 H 0.3415 0.6954 0.4971 0.0323 1.0000 Uiso R . . . .
H152 H 0.1952 0.7917 0.5082 0.0315 1.0000 Uiso R . . . .
H161 H 0.3500 0.8190 0.4305 0.0252 1.0000 Uiso R . . . .
H181 H 0.1885 1.1051 0.4994 0.0544 1.0000 Uiso R . . . .
H182 H 0.2601 0.9852 0.5242 0.0541 1.0000 Uiso R . . . .
H183 H 0.3694 1.1057 0.5119 0.0539 1.0000 Uiso R . . . .
H191 H 0.3870 1.0272 0.4038 0.0293 1.0000 Uiso R . . . .
H192 H 0.3008 1.1487 0.4268 0.0293 1.0000 Uiso R . . . .
H201 H 0.5592 1.2191 0.4196 0.0290 1.0000 Uiso R . . . .
H202 H 0.5436 1.1780 0.4662 0.0290 1.0000 Uiso R . . . .
H211 H 0.6501 0.9560 0.4376 0.0274 1.0000 Uiso R . . . .
H231 H 0.8116 1.2686 0.4173 0.0518 1.0000 Uiso R . . . .
H232 H 0.9262 1.2094 0.3823 0.0514 1.0000 Uiso R . . . .
H233 H 0.9793 1.2225 0.4303 0.0527 1.0000 Uiso R . . . .
H241 H 1.0149 0.9548 0.4399 0.0325 1.0000 Uiso R . . . .
H242 H 0.8738 0.8668 0.4220 0.0316 1.0000 Uiso R . . . .
H251 H 1.1009 0.8633 0.3778 0.0305 1.0000 Uiso R . . . .
H252 H 1.0820 1.0204 0.3713 0.0296 1.0000 Uiso R . . . .
H261 H 0.8297 0.9740 0.3404 0.0227 1.0000 Uiso R . . . .
H281 H 1.1018 1.0641 0.2636 0.0461 0.9474(12) Uiso R . P 1 1
H282 H 1.1293 1.0916 0.3101 0.0461 0.9474(12) Uiso R . P 1 1
H283 H 0.9657 1.1211 0.2904 0.0461 0.9474(12) Uiso R . P 1 1
H301 H 0.9276 0.8935 0.2367 0.0445 0.8335(14) Uiso R . P 1 7
H302 H 0.7878 0.9435 0.2636 0.0445 0.8335(14) Uiso R . P 1 7
H303 H 0.8481 0.7986 0.2682 0.0445 0.8335(14) Uiso R . P 1 7
H291 H 1.1885 0.8331 0.2712 0.0515 0.2191(14) Uiso R . P 1 4
H292 H 1.2166 0.8512 0.3182 0.0515 0.2191(14) Uiso R . P 1 4
H293 H 1.1077 0.7379 0.3024 0.0515 0.2191(14) Uiso R . P 1 4
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02443(15) 0.03813(18) 0.03268(17) -0.00048(15) 0.00887(14) 0.01134(15)
Br2 0.0380(14) 0.0260(10) 0.0357(11) -0.0039(9) -0.0017(10) 0.0010(9)
O1 0.0171(8) 0.0173(8) 0.0288(8) 0.0012(6) -0.0001(6) -0.0002(6)
O2 0.0211(8) 0.0201(8) 0.0429(10) -0.0029(7) 0.0037(7) 0.0021(7)
O3 0.0276(8) 0.0149(7) 0.0257(8) -0.0035(6) 0.0046(7) -0.0012(6)
O4 0.0275(8) 0.0282(8) 0.0212(8) -0.0044(7) 0.0011(7) 0.0030(7)
C1 0.0183(11) 0.0219(11) 0.0195(10) 0.0014(8) -0.0003(9) 0.0003(9)
C2 0.0193(11) 0.0203(11) 0.0162(10) 0.0020(8) -0.0006(8) -0.0001(8)
C3 0.0206(11) 0.0250(12) 0.0235(12) 0.0007(9) 0.0004(9) 0.0022(9)
C4 0.0247(11) 0.0205(10) 0.0246(11) -0.0013(8) 0.0015(10) 0.0049(10)
C5 0.0237(11) 0.0174(11) 0.0171(11) 0.0016(8) -0.0006(9) 0.0014(9)
C6 0.0204(11) 0.0191(11) 0.0145(10) -0.0004(8) 0.0013(9) 0.0003(9)
C7 0.0212(11) 0.0208(11) 0.0158(10) -0.0012(8) 0.0017(9) 0.0011(9)
C8 0.0321(13) 0.0177(11) 0.0221(12) 0.0012(9) 0.0028(10) 0.0041(10)
C9 0.0371(15) 0.0534(17) 0.0245(13) -0.0101(12) -0.0010(11) -0.0014(13)
C10 0.0233(12) 0.0244(12) 0.0241(12) -0.0050(10) 0.0045(9) -0.0024(9)
C11 0.0163(10) 0.0180(10) 0.0265(11) -0.0002(8) 0.0032(10) -0.0015(9)
C12 0.0185(11) 0.0172(10) 0.0235(11) 0.0018(9) 0.0036(8) -0.0003(8)
C13 0.0460(17) 0.0398(14) 0.0320(14) -0.0001(11) -0.0014(13) 0.0196(13)
C14 0.0220(12) 0.0233(11) 0.0213(11) 0.0024(9) 0.0063(9) 0.0011(9)
C15 0.0299(12) 0.0288(12) 0.0189(11) -0.0027(10) 0.0003(10) 0.0002(10)
C16 0.0192(10) 0.0251(10) 0.0162(10) -0.0023(8) -0.0021(9) 0.0033(10)
C17 0.0129(9) 0.0283(11) 0.0206(10) -0.0016(8) 0.0001(9) -0.0009(10)
C18 0.0345(14) 0.0299(13) 0.0361(14) -0.0081(11) 0.0129(11) -0.0020(10)
C19 0.0208(11) 0.0240(12) 0.0251(12) -0.0002(9) -0.0023(9) 0.0036(9)
C20 0.0219(12) 0.0226(11) 0.0261(12) -0.0027(9) 0.0011(9) 0.0003(9)
C21 0.0225(10) 0.0221(10) 0.0179(10) 0.0008(8) -0.0026(10) 0.0030(10)
C22 0.0210(10) 0.0288(11) 0.0137(10) -0.0025(8) -0.0061(9) 0.0021(10)
C23 0.0256(11) 0.0310(12) 0.0416(14) -0.0085(12) 0.0023(10) -0.0039(12)
C24 0.0168(11) 0.0360(13) 0.0247(12) 0.0015(10) -0.0041(9) 0.0043(10)
C25 0.0174(11) 0.0294(12) 0.0240(12) -0.0019(10) 0.0009(9) 0.0019(9)
C26 0.0161(11) 0.0160(10) 0.0267(12) 0.0010(9) 0.0020(9) 0.0006(8)
C27 0.0295(12) 0.0287(11) 0.0221(12) -0.0016(10) 0.0023(10) 0.0027(9)
C28 0.057(2) 0.0245(16) 0.0423(19) 0.0222(15) 0.0258(16) 0.0100(15)
C30 0.034(3) 0.036(3) 0.077(5) -0.004(3) -0.003(3) 0.002(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C26 116.88(15) yes
C5 O3 C8 118.19(16) yes
C8 O4 C9 113.05(17) yes
O1 C1 O2 123.89(18) yes
O1 C1 C2 112.39(17) yes
O2 C1 C2 123.71(19) yes
C1 C2 C3 123.01(19) yes
C1 C2 C7 117.48(18) yes
C3 C2 C7 119.39(19) yes
C2 C3 C4 119.7(2) yes
C2 C3 H31 119.8 no
C4 C3 H31 120.5 no
C3 C4 C5 120.0(2) yes
C3 C4 H41 119.2 no
C5 C4 H41 120.8 no
C4 C5 O3 123.71(18) yes
C4 C5 C6 121.22(19) yes
O3 C5 C6 115.07(18) yes
C5 C6 C7 117.52(19) yes
C5 C6 C10 120.49(19) yes
C7 C6 C10 121.99(19) yes
C2 C7 C6 122.1(2) yes
C2 C7 H71 117.7 no
C6 C7 H71 120.3 no
O3 C8 O4 113.06(17) yes
O3 C8 H81 106.4 no
O4 C8 H81 108.9 no
O3 C8 H82 109.2 no
O4 C8 H82 107.6 no
H81 C8 H82 111.8 no
O4 C9 H91 105.4 no
O4 C9 H92 110.1 no
H91 C9 H92 113.8 no
O4 C9 H93 106.6 no
H91 C9 H93 111.6 no
H92 C9 H93 109.2 no
C6 C10 C11 114.53(19) yes
C6 C10 H101 108.8 no
C11 C10 H101 108.9 no
C6 C10 H102 108.6 no
C11 C10 H102 106.9 no
H101 C10 H102 109.0 no
C10 C11 C12 125.0(2) yes
C10 C11 H111 116.8 no
C12 C11 H111 118.1 no
C11 C12 C13 122.5(2) yes
C11 C12 C14 122.3(2) yes
C13 C12 C14 115.20(18) yes
C12 C13 H131 111.6 no
C12 C13 H132 107.9 no
H131 C13 H132 110.0 no
C12 C13 H133 108.5 no
H131 C13 H133 110.8 no
H132 C13 H133 108.0 no
C12 C14 C15 115.17(18) yes
C12 C14 H141 107.8 no
C15 C14 H141 110.7 no
C12 C14 H142 107.6 no
C15 C14 H142 107.8 no
H141 C14 H142 107.6 no
C14 C15 C16 113.38(18) yes
C14 C15 H151 106.6 no
C16 C15 H151 111.1 no
C14 C15 H152 106.9 no
C16 C15 H152 109.2 no
H151 C15 H152 109.5 no
C15 C16 C17 127.41(19) yes
C15 C16 H161 114.1 no
C17 C16 H161 118.5 no
C16 C17 C18 124.1(2) yes
C16 C17 C19 121.42(19) yes
C18 C17 C19 114.48(18) yes
C17 C18 H181 111.6 no
C17 C18 H182 111.8 no
H181 C18 H182 109.1 no
C17 C18 H183 108.7 no
H181 C18 H183 107.6 no
H182 C18 H183 107.9 no
C17 C19 C20 114.19(19) yes
C17 C19 H191 108.2 no
C20 C19 H191 108.3 no
C17 C19 H192 108.7 no
C20 C19 H192 107.5 no
H191 C19 H192 110.0 no
C19 C20 C21 111.12(18) yes
C19 C20 H201 111.4 no
C21 C20 H201 109.9 no
C19 C20 H202 109.6 no
C21 C20 H202 109.5 no
H201 C20 H202 105.1 no
C20 C21 C22 128.9(2) yes
C20 C21 H211 116.9 no
C22 C21 H211 114.2 no
C21 C22 C23 124.0(2) yes
C21 C22 C24 119.7(2) yes
C23 C22 C24 116.2(2) yes
C22 C23 H231 110.5 no
C22 C23 H232 112.1 no
H231 C23 H232 107.9 no
C22 C23 H233 112.2 no
H231 C23 H233 105.4 no
H232 C23 H233 108.4 no
C22 C24 C25 115.81(19) yes
C22 C24 H241 110.2 no
C25 C24 H241 107.8 no
C22 C24 H242 107.5 no
C25 C24 H242 107.6 no
H241 C24 H242 107.6 no
C24 C25 C26 113.34(18) yes
C24 C25 H251 110.9 no
C26 C25 H251 106.7 no
C24 C25 H252 109.4 no
C26 C25 H252 107.3 no
H251 C25 H252 109.0 no
C25 C26 O1 107.45(16) yes
C25 C26 C27 114.06(15) yes
O1 C26 C27 108.92(15) yes
C25 C26 H261 109.5 no
O1 C26 H261 108.8 no
C27 C26 H261 107.9 no
C26 C27 C28 110.6(2) yes
C26 C27 Br3 108.48(14) yes
C26 C27 Br1 111.61(14) yes
C26 C27 C29 108.56(14) yes
C26 C27 Br2 110.96(12) yes
C26 C27 C30 109.9(3) yes
C27 C28 H281 107.0 no
C27 C28 H282 112.4 no
H281 C28 H282 109.5 no
C27 C28 H283 108.9 no
H281 C28 H283 109.5 no
H282 C28 H283 109.5 no
C27 C29 H291 106.8 no
C27 C29 H292 111.3 no
H291 C29 H292 109.5 no
C27 C29 H293 110.2 no
H291 C29 H293 109.5 no
H292 C29 H293 109.5 no
C27 C30 H301 111.2 no
C27 C30 H302 112.3 no
H301 C30 H302 109.5 no
C27 C30 H303 104.8 no
H301 C30 H303 109.5 no
H302 C30 H303 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C27 1.9191(19) yes
Br2 C27 1.928(4) yes
Br3 C27 1.918(4) yes
O1 C1 1.355(3) yes
O1 C26 1.445(2) yes
O2 C1 1.202(2) yes
O3 C5 1.376(2) yes
O3 C8 1.430(2) yes
O4 C8 1.391(3) yes
O4 C9 1.423(3) yes
C1 C2 1.485(3) yes
C2 C3 1.392(3) yes
C2 C7 1.393(3) yes
C3 C4 1.383(3) yes
C3 H31 0.962 no
C4 C5 1.391(3) yes
C4 H41 0.956 no
C5 C6 1.403(3) yes
C6 C7 1.380(3) yes
C6 C10 1.517(3) yes
C7 H71 0.950 no
C8 H81 0.963 no
C8 H82 0.995 no
C9 H91 0.967 no
C9 H92 1.001 no
C9 H93 0.968 no
C10 C11 1.516(3) yes
C10 H101 0.969 no
C10 H102 0.964 no
C11 C12 1.327(3) yes
C11 H111 0.951 no
C12 C13 1.501(3) yes
C12 C14 1.506(3) yes
C13 H131 0.974 no
C13 H132 0.968 no
C13 H133 0.979 no
C14 C15 1.534(3) yes
C14 H141 1.005 no
C14 H142 0.986 no
C15 C16 1.508(3) yes
C15 H151 0.977 no
C15 H152 0.995 no
C16 C17 1.326(3) yes
C16 H161 0.944 no
C17 C18 1.505(3) yes
C17 C19 1.509(3) yes
C18 H181 0.969 no
C18 H182 0.959 no
C18 H183 0.989 no
C19 C20 1.537(3) yes
C19 H191 0.970 no
C19 H192 0.992 no
C20 C21 1.496(3) yes
C20 H201 0.988 no
C20 H202 0.990 no
C21 C22 1.329(3) yes
C21 H211 0.920 no
C22 C23 1.504(3) yes
C22 C24 1.510(3) yes
C23 H231 0.965 no
C23 H232 1.020 no
C23 H233 0.981 no
C24 C25 1.528(3) yes
C24 H241 0.976 no
C24 H242 0.999 no
C25 C26 1.537(3) yes
C25 H251 0.988 no
C25 H252 0.981 no
C26 C27 1.537(3) yes
C26 H261 0.953 no
C27 C28 1.522(4) yes
C27 C29 1.549(7) yes
C27 C30 1.546(7) yes
C28 H281 0.950 no
C28 H282 0.950 no
C28 H283 0.950 no
C29 H291 0.950 no
C29 H292 0.950 no
C29 H293 0.950 no
C30 H301 0.950 no
C30 H302 0.950 no
C30 H303 0.950 no
|
1502028.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502028.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502028
loop_
_publ_author_name
'Chen, Jinshui'
'Captain, Burjor'
'Takenaka, Norito'
_publ_section_title
;
Helical chiral 2,2'-bipyridine N-monoxides as catalysts in the
enantioselective propargylation of aldehydes with allenyltrichlorosilane.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1654
_journal_page_last 1657
_journal_paper_doi 10.1021/ol200102c
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C34 H20 N2 O'
_chemical_formula_weight 472.52
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.3737(3)
_cell_length_b 12.6257(5)
_cell_length_c 21.4999(8)
_cell_measurement_reflns_used 9889
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 32.40
_cell_measurement_theta_min 2.49
_cell_volume 2273.05(15)
_computing_cell_refinement 'SAINT+ V7.46A (Bruker, 2007)'
_computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction 'SAINT+ V7.46A (Bruker, 2007)'
_computing_molecular_graphics 'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material 'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method 'omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0215
_diffrn_reflns_av_sigmaI/netI 0.0164
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 24872
_diffrn_reflns_theta_full 29.00
_diffrn_reflns_theta_max 29.00
_diffrn_reflns_theta_min 1.87
_exptl_absorpt_coefficient_mu 0.084
_exptl_absorpt_correction_T_max 0.9975
_exptl_absorpt_correction_T_min 0.9625
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour Yellow
_exptl_crystal_density_diffrn 1.381
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Plate
_exptl_crystal_F_000 984
_exptl_crystal_size_max 0.46
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.212
_refine_diff_density_min -0.233
_refine_diff_density_rms 0.054
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.021
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 334
_refine_ls_number_reflns 6036
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.021
_refine_ls_R_factor_all 0.0450
_refine_ls_R_factor_gt 0.0391
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.1995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1060
_refine_ls_wR_factor_ref 0.1122
_reflns_number_gt 5402
_reflns_number_total 6036
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200102c_si_001.cif
_cod_data_source_block collect_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.
'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1502028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.98353(11) 0.53475(7) 0.78821(4) 0.0433(2) Uani 1 1 d .
N1 N 0.92567(13) 0.62658(8) 0.80321(5) 0.0391(2) Uani 1 1 d .
N2 N 1.1235(2) 0.69475(10) 0.94815(6) 0.0613(4) Uani 1 1 d .
C2 C 0.98328(16) 0.68153(10) 0.85295(6) 0.0413(3) Uani 1 1 d .
C3 C 0.9458(2) 0.79014(11) 0.85730(8) 0.0556(4) Uani 1 1 d .
H3 H 0.9823 0.8288 0.8912 0.067 Uiso 1 1 calc R
C4 C 0.8577(2) 0.83921(12) 0.81310(9) 0.0631(4) Uani 1 1 d .
H4 H 0.8459 0.9124 0.8138 0.076 Uiso 1 1 calc R
C5 C 0.6929(2) 0.82613(16) 0.71688(9) 0.0688(5) Uani 1 1 d .
H5 H 0.6776 0.8991 0.7160 0.083 Uiso 1 1 calc R
C6 C 0.6293(2) 0.76488(19) 0.67190(8) 0.0724(6) Uani 1 1 d .
H6 H 0.5815 0.7970 0.6377 0.087 Uiso 1 1 calc R
C7 C 0.5608(3) 0.5893(2) 0.62774(8) 0.0794(6) Uani 1 1 d .
H7 H 0.5049 0.6222 0.5957 0.095 Uiso 1 1 calc R
C8 C 0.5722(3) 0.4833(2) 0.62865(8) 0.0796(6) Uani 1 1 d .
H8 H 0.5371 0.4446 0.5945 0.095 Uiso 1 1 calc R
C9 C 0.6500(2) 0.31713(17) 0.68226(8) 0.0705(5) Uani 1 1 d .
H9 H 0.6144 0.2780 0.6483 0.085 Uiso 1 1 calc R
C10 C 0.7125(2) 0.26631(15) 0.73124(8) 0.0631(5) Uani 1 1 d .
H10 H 0.7335 0.1941 0.7286 0.076 Uiso 1 1 calc R
C11 C 0.81778(18) 0.26912(11) 0.84098(7) 0.0468(3) Uani 1 1 d .
C12 C 0.83284(18) 0.32355(10) 0.89779(7) 0.0445(3) Uani 1 1 d .
C13 C 0.74433(19) 0.47781(11) 0.96255(6) 0.0453(3) Uani 1 1 d .
H13 H 0.7928 0.4472 0.9971 0.054 Uiso 1 1 calc R
C14 C 0.6622(2) 0.57017(11) 0.96977(6) 0.0501(3) Uani 1 1 d .
H14 H 0.6575 0.6029 1.0085 0.060 Uiso 1 1 calc R
C15 C 0.5856(2) 0.61514(11) 0.91891(6) 0.0491(3) Uani 1 1 d .
H15 H 0.5239 0.6758 0.9240 0.059 Uiso 1 1 calc R
C16 C 0.60077(17) 0.56997(10) 0.86097(6) 0.0420(3) Uani 1 1 d .
H16 H 0.5488 0.6006 0.8272 0.050 Uiso 1 1 calc R
C17 C 0.78400(19) 0.77913(13) 0.76598(7) 0.0540(4) Uani 1 1 d .
C18 C 0.80396(16) 0.66857(11) 0.76578(6) 0.0438(3) Uani 1 1 d .
C19 C 0.6332(2) 0.65260(17) 0.67530(7) 0.0619(4) Uani 1 1 d .
C20 C 0.71006(16) 0.60147(13) 0.72596(6) 0.0475(3) Uani 1 1 d .
C21 C 0.6367(2) 0.42918(17) 0.68082(7) 0.0627(4) Uani 1 1 d .
C22 C 0.68715(17) 0.48825(13) 0.73351(6) 0.0478(3) Uani 1 1 d .
C23 C 0.74722(17) 0.32169(11) 0.78743(7) 0.0464(3) Uani 1 1 d .
C24 C 0.71325(15) 0.43039(11) 0.79026(6) 0.0408(3) Uani 1 1 d .
C25 C 0.75796(17) 0.42750(9) 0.90444(6) 0.0384(2) Uani 1 1 d .
C26 C 0.69342(15) 0.47822(9) 0.85173(5) 0.0363(2) Uani 1 1 d .
C27 C 0.8861(2) 0.16614(12) 0.83677(9) 0.0619(5) Uani 1 1 d .
H27 H 0.8753 0.1280 0.8000 0.074 Uiso 1 1 calc R
C28 C 0.9667(3) 0.12216(13) 0.88524(11) 0.0750(6) Uani 1 1 d .
H28 H 1.0119 0.0553 0.8809 0.090 Uiso 1 1 calc R
C29 C 0.9817(3) 0.17568(14) 0.94055(11) 0.0760(6) Uani 1 1 d .
H29 H 1.0371 0.1452 0.9735 0.091 Uiso 1 1 calc R
C30 C 0.9144(2) 0.27472(12) 0.94714(8) 0.0622(4) Uani 1 1 d .
H30 H 0.9231 0.3099 0.9850 0.075 Uiso 1 1 calc R
C31 C 1.08424(16) 0.62977(10) 0.90077(6) 0.0408(3) Uani 1 1 d .
C32 C 1.13024(19) 0.52384(11) 0.90132(7) 0.0507(3) Uani 1 1 d .
H32 H 1.1079 0.4801 0.8676 0.061 Uiso 1 1 calc R
C33 C 1.2097(2) 0.48477(13) 0.95285(8) 0.0591(4) Uani 1 1 d .
H33 H 1.2390 0.4138 0.9544 0.071 Uiso 1 1 calc R
C34 C 1.2452(2) 0.55032(14) 1.00128(7) 0.0614(4) Uani 1 1 d .
H34 H 1.2965 0.5251 1.0367 0.074 Uiso 1 1 calc R
C35 C 1.2025(3) 0.65458(15) 0.99600(8) 0.0710(5) Uani 1 1 d .
H35 H 1.2309 0.7002 1.0281 0.085 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0473(5) 0.0386(4) 0.0441(5) -0.0022(4) 0.0021(4) 0.0015(4)
N1 0.0388(5) 0.0373(5) 0.0413(5) 0.0060(4) 0.0051(4) -0.0009(4)
N2 0.0792(10) 0.0501(7) 0.0547(7) -0.0130(6) -0.0095(7) 0.0046(7)
C2 0.0413(6) 0.0357(6) 0.0470(7) 0.0014(5) 0.0046(5) -0.0031(5)
C3 0.0590(9) 0.0373(6) 0.0704(10) -0.0017(6) 0.0009(8) -0.0003(6)
C4 0.0650(10) 0.0370(7) 0.0874(12) 0.0099(7) 0.0052(9) 0.0056(7)
C5 0.0629(9) 0.0720(11) 0.0715(11) 0.0346(9) 0.0136(9) 0.0190(9)
C6 0.0590(10) 0.1048(15) 0.0534(9) 0.0385(10) 0.0086(8) 0.0211(10)
C7 0.0613(10) 0.141(2) 0.0356(7) 0.0127(10) -0.0053(7) 0.0087(12)
C8 0.0697(11) 0.133(2) 0.0359(7) -0.0106(10) -0.0076(7) -0.0088(13)
C9 0.0657(10) 0.0945(14) 0.0512(9) -0.0343(9) 0.0053(8) -0.0226(10)
C10 0.0629(10) 0.0659(10) 0.0604(9) -0.0282(8) 0.0152(8) -0.0193(8)
C11 0.0492(7) 0.0343(6) 0.0568(7) -0.0059(5) 0.0177(6) -0.0092(5)
C12 0.0487(7) 0.0335(6) 0.0512(7) 0.0012(5) 0.0079(6) -0.0027(5)
C13 0.0587(8) 0.0415(7) 0.0358(6) 0.0029(5) 0.0009(5) -0.0004(6)
C14 0.0694(10) 0.0453(7) 0.0357(6) -0.0049(5) 0.0093(6) 0.0029(7)
C15 0.0585(8) 0.0414(6) 0.0473(7) -0.0002(5) 0.0125(6) 0.0087(6)
C16 0.0445(7) 0.0439(6) 0.0376(6) 0.0037(5) 0.0054(5) 0.0018(5)
C17 0.0501(8) 0.0529(8) 0.0591(8) 0.0200(7) 0.0111(7) 0.0091(7)
C18 0.0410(6) 0.0508(7) 0.0396(6) 0.0118(5) 0.0065(5) 0.0025(6)
C19 0.0477(8) 0.1005(13) 0.0377(7) 0.0183(7) 0.0059(6) 0.0093(8)
C20 0.0412(7) 0.0699(9) 0.0314(6) 0.0080(6) 0.0046(5) 0.0030(6)
C21 0.0520(8) 0.0989(13) 0.0372(7) -0.0139(7) 0.0016(6) -0.0131(9)
C22 0.0410(6) 0.0696(9) 0.0329(6) -0.0051(6) 0.0020(5) -0.0059(6)
C23 0.0455(6) 0.0474(7) 0.0462(7) -0.0136(6) 0.0124(6) -0.0125(6)
C24 0.0384(6) 0.0472(7) 0.0368(6) -0.0064(5) 0.0042(5) -0.0079(5)
C25 0.0434(6) 0.0320(5) 0.0399(6) 0.0000(5) 0.0049(5) -0.0029(5)
C26 0.0380(6) 0.0364(6) 0.0345(5) -0.0017(5) 0.0050(4) -0.0057(5)
C27 0.0717(11) 0.0378(7) 0.0761(11) -0.0096(7) 0.0318(9) -0.0079(7)
C28 0.0814(13) 0.0369(7) 0.1066(15) 0.0101(9) 0.0308(11) 0.0104(8)
C29 0.0833(13) 0.0499(9) 0.0949(14) 0.0179(9) 0.0036(11) 0.0162(9)
C30 0.0750(11) 0.0444(7) 0.0672(9) 0.0079(7) -0.0026(9) 0.0077(8)
C31 0.0395(6) 0.0392(6) 0.0438(6) -0.0014(5) 0.0018(5) -0.0048(5)
C32 0.0536(8) 0.0426(7) 0.0559(8) -0.0065(6) -0.0105(6) 0.0018(6)
C33 0.0591(10) 0.0502(8) 0.0679(10) 0.0024(7) -0.0108(8) 0.0050(7)
C34 0.0623(9) 0.0725(10) 0.0494(8) 0.0041(7) -0.0073(7) 0.0068(8)
C35 0.0907(14) 0.0711(10) 0.0512(9) -0.0170(8) -0.0162(9) 0.0109(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N1 C2 121.19(11)
O1 N1 C18 117.82(11)
C2 N1 C18 120.99(11)
C35 N2 C31 118.40(14)
N1 C2 C3 117.92(13)
N1 C2 C31 121.42(11)
C3 C2 C31 120.65(13)
C4 C3 C2 121.35(16)
C3 C4 C17 119.84(14)
C6 C5 C17 120.13(18)
C5 C6 C19 121.78(15)
C8 C7 C19 121.05(18)
C7 C8 C21 121.24(18)
C10 C9 C21 121.68(15)
C9 C10 C23 120.72(17)
C12 C11 C27 117.74(15)
C12 C11 C23 120.04(12)
C27 C11 C23 121.99(14)
C30 C12 C11 119.01(13)
C30 C12 C25 121.93(13)
C11 C12 C25 119.02(13)
C14 C13 C25 121.92(13)
C13 C14 C15 119.56(12)
C16 C15 C14 120.03(13)
C15 C16 C26 121.31(12)
C18 C17 C4 119.00(14)
C18 C17 C5 118.22(18)
C4 C17 C5 122.76(16)
N1 C18 C17 117.39(14)
N1 C18 C20 121.06(13)
C17 C18 C20 121.44(14)
C6 C19 C20 120.25(17)
C6 C19 C7 120.68(17)
C20 C19 C7 119.07(19)
C19 C20 C18 115.88(15)
C19 C20 C22 118.26(15)
C18 C20 C22 125.86(12)
C9 C21 C22 118.86(16)
C9 C21 C8 121.78(17)
C22 C21 C8 119.35(19)
C21 C22 C24 117.05(15)
C21 C22 C20 117.85(14)
C24 C22 C20 125.09(12)
C24 C23 C10 118.37(15)
C24 C23 C11 119.64(12)
C10 C23 C11 121.99(14)
C23 C24 C22 119.39(12)
C23 C24 C26 117.79(12)
C22 C24 C26 122.64(12)
C13 C25 C26 118.56(11)
C13 C25 C12 121.83(12)
C26 C25 C12 119.59(11)
C16 C26 C25 118.13(11)
C16 C26 C24 121.99(11)
C25 C26 C24 119.70(11)
C28 C27 C11 121.57(16)
C27 C28 C29 120.53(15)
C28 C29 C30 119.84(19)
C29 C30 C12 121.29(18)
N2 C31 C32 120.70(13)
N2 C31 C2 113.24(12)
C32 C31 C2 125.97(12)
C33 C32 C31 118.86(14)
C34 C33 C32 120.01(15)
C33 C34 C35 117.64(15)
N2 C35 C34 124.28(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2972(14)
N1 C2 1.3631(17)
N1 C18 1.4025(17)
N2 C35 1.324(2)
N2 C31 1.3489(18)
C2 C3 1.4099(19)
C2 C31 1.483(2)
C3 C4 1.353(2)
C4 C17 1.408(3)
C5 C6 1.348(3)
C5 C17 1.431(2)
C6 C19 1.420(3)
C7 C8 1.342(3)
C7 C19 1.432(3)
C8 C21 1.421(3)
C9 C10 1.340(3)
C9 C21 1.419(3)
C10 C23 1.4258(19)
C11 C12 1.407(2)
C11 C27 1.423(2)
C11 C23 1.454(2)
C12 C30 1.404(2)
C12 C25 1.4615(17)
C13 C14 1.363(2)
C13 C25 1.4062(17)
C14 C15 1.389(2)
C15 C16 1.3759(18)
C16 C26 1.4084(18)
C17 C18 1.406(2)
C18 C20 1.438(2)
C19 C20 1.420(2)
C20 C22 1.451(2)
C21 C22 1.420(2)
C22 C24 1.4388(19)
C23 C24 1.403(2)
C24 C26 1.4624(16)
C25 C26 1.4095(17)
C27 C28 1.360(3)
C28 C29 1.374(3)
C29 C30 1.379(2)
C31 C32 1.3918(19)
C32 C33 1.383(2)
C33 C34 1.363(2)
C34 C35 1.369(3)
|
1502029.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502029.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502029
loop_
_publ_author_name
'Hara, Noriyuki'
'Tamura, Ryota'
'Funahashi, Yasuhiro'
'Nakamura, Shuichi'
_publ_section_title
;
N-(heteroarenesulfonyl)prolinamides-catalyzed aldol reaction between
acetone and aryl trihalomethyl ketones.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1662
_journal_page_last 1665
_journal_paper_doi 10.1021/ol2001039
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety 'C13 H13 Cl3 O2'
_chemical_formula_sum 'C13 H13 Cl3 O2'
_chemical_formula_weight 307.60
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 4
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha 90.0000
_cell_angle_beta 98.522(7)
_cell_angle_gamma 90.0000
_cell_formula_units_Z 2
_cell_length_a 8.096(4)
_cell_length_b 6.072(3)
_cell_length_c 14.533(7)
_cell_measurement_reflns_used 2293
_cell_measurement_temperature 173(1)
_cell_measurement_theta_max 30.77
_cell_measurement_theta_min 2.54
_cell_volume 706.5(6)
_computing_cell_refinement CrystalClear
_computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction CrystalClear
_computing_molecular_graphics 'CrystalStructure 4.0'
_computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution 'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature 173(1)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'Rigaku Mercury70'
_diffrn_measurement_method \w
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71070
_diffrn_reflns_av_R_equivalents 0.0208
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 5271
_diffrn_reflns_theta_full 27.59
_diffrn_reflns_theta_max 27.59
_exptl_absorpt_coefficient_mu 0.638
_exptl_absorpt_correction_T_max 0.950
_exptl_absorpt_correction_T_min 0.781
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'REQAB (Rigaku, 1998)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.446
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 316.00
_exptl_crystal_size_max 0.250
_exptl_crystal_size_mid 0.080
_exptl_crystal_size_min 0.080
_refine_diff_density_max 0.538
_refine_diff_density_min -0.414
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1384 Friedel Pairs'
_refine_ls_abs_structure_Flack -0.03(6)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.274
_refine_ls_hydrogen_treatment constr
_refine_ls_number_parameters 195
_refine_ls_number_reflns 3156
_refine_ls_R_factor_gt 0.0338
_refine_ls_shift/su_max 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details 'w = 1/[1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.0632
_reflns_number_gt 2765
_reflns_number_total 3156
_reflns_threshold_expression F^2^>2.0\s(F^2^)
_cod_data_source_file ol2001039_si_001.cif
_cod_data_source_block '__1-(2-naphthyl)-2,2,2-trichloroethanone'
_cod_database_code 1502029
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.30693(10) 0.66930(13) 0.32263(5) 0.0372(3) Uani 1.0 2 d .
Cl2 Cl 0.44869(10) 0.33416(14) 0.44874(5) 0.0379(3) Uani 1.0 2 d .
Cl3 Cl 0.17295(9) 0.23067(14) 0.30972(5) 0.0359(3) Uani 1.0 2 d .
O1 O 0.5072(3) 0.0920(3) 0.27168(14) 0.0316(6) Uani 1.0 2 d .
O22 O 0.7976(3) 0.1554(4) 0.37777(17) 0.0498(8) Uani 1.0 2 d .
C1 C 0.4854(4) 0.3202(5) 0.26371(18) 0.0234(8) Uani 1.0 2 d .
C2 C 0.3598(4) 0.3851(5) 0.33181(19) 0.0276(8) Uani 1.0 2 d .
C3 C 0.6517(4) 0.4462(5) 0.2908(2) 0.0306(9) Uani 1.0 2 d .
C4 C 0.7761(4) 0.3517(6) 0.3695(3) 0.0362(10) Uani 1.0 2 d .
C5 C 0.8790(4) 0.5152(6) 0.4291(3) 0.0518(12) Uani 1.0 2 d .
C6 C 0.4072(4) 0.3698(5) 0.16383(18) 0.0234(8) Uani 1.0 2 d .
C7 C 0.3101(3) 0.2141(5) 0.11388(18) 0.0243(8) Uani 1.0 2 d .
C8 C 0.2369(3) 0.2516(5) 0.02147(19) 0.0231(8) Uani 1.0 2 d .
C9 C 0.1305(4) 0.0967(5) -0.0300(2) 0.0285(9) Uani 1.0 2 d .
C10 C 0.0598(4) 0.1380(5) -0.1198(2) 0.0341(10) Uani 1.0 2 d .
C11 C 0.0942(4) 0.3341(6) -0.1624(2) 0.0368(9) Uani 1.0 2 d .
C12 C 0.1955(4) 0.4887(5) -0.1149(2) 0.0335(10) Uani 1.0 2 d .
C13 C 0.2665(4) 0.4552(5) -0.0217(2) 0.0248(8) Uani 1.0 2 d .
C14 C 0.3695(4) 0.6138(5) 0.0305(2) 0.0268(9) Uani 1.0 2 d .
C15 C 0.4350(4) 0.5731(5) 0.1207(2) 0.0263(9) Uani 1.0 2 d .
H1 H 0.5855 0.0642 0.3161 0.0374 Uiso 1.0 2 calc R
H2 H 0.7094 0.4536 0.2369 0.0363 Uiso 1.0 2 calc R
H3 H 0.6267 0.5941 0.3098 0.0364 Uiso 1.0 2 calc R
H4 H 0.9943 0.4985 0.4219 0.0609 Uiso 1.0 2 calc R
H5 H 0.8427 0.6618 0.4115 0.0609 Uiso 1.0 2 calc R
H6 H 0.8664 0.4900 0.4929 0.0610 Uiso 1.0 2 calc R
H7 H 0.2923 0.0800 0.1417 0.0295 Uiso 1.0 2 calc R
H8 H 0.1078 -0.0355 -0.0021 0.0344 Uiso 1.0 2 calc R
H9 H -0.0098 0.0338 -0.1525 0.0405 Uiso 1.0 2 calc R
H10 H 0.0466 0.3611 -0.2236 0.0434 Uiso 1.0 2 calc R
H11 H 0.2181 0.6182 -0.1448 0.0409 Uiso 1.0 2 calc R
H12 H 0.3929 0.7462 0.0030 0.0322 Uiso 1.0 2 calc R
H13 H 0.4987 0.6814 0.1546 0.0316 Uiso 1.0 2 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0435(5) 0.0230(4) 0.0465(5) 0.0052(4) 0.0109(4) -0.0001(4)
Cl2 0.0425(5) 0.0406(5) 0.0302(4) -0.0026(4) 0.0042(4) 0.0037(4)
Cl3 0.0273(4) 0.0358(5) 0.0459(5) -0.0081(4) 0.0093(4) -0.0004(4)
O1 0.0342(13) 0.0207(11) 0.0378(13) -0.0002(10) -0.0015(10) -0.0001(9)
O22 0.0341(15) 0.0421(16) 0.0692(18) 0.0062(12) -0.0058(12) 0.0078(14)
C1 0.0216(15) 0.0182(14) 0.0308(16) -0.0022(12) 0.0053(12) 0.0021(13)
C2 0.0266(16) 0.0231(17) 0.0329(17) -0.0039(13) 0.0036(13) 0.0012(12)
C3 0.0231(16) 0.0311(17) 0.0372(18) -0.0039(13) 0.0033(14) -0.0047(14)
C4 0.0235(17) 0.046(3) 0.0397(19) 0.0009(16) 0.0072(13) -0.0047(17)
C5 0.035(3) 0.066(3) 0.050(3) 0.0049(19) -0.0104(16) -0.016(2)
C6 0.0238(15) 0.0170(15) 0.0303(16) 0.0006(12) 0.0065(12) -0.0003(12)
C7 0.0258(15) 0.0193(15) 0.0284(15) -0.0005(13) 0.0065(12) 0.0006(12)
C8 0.0187(14) 0.0224(15) 0.0284(15) 0.0027(12) 0.0044(11) -0.0018(13)
C9 0.0288(17) 0.0239(16) 0.0333(18) 0.0003(13) 0.0061(13) 0.0003(13)
C10 0.0289(18) 0.039(2) 0.0334(18) -0.0004(15) 0.0000(14) -0.0092(15)
C11 0.0360(19) 0.0423(19) 0.0308(17) 0.0078(17) 0.0001(14) 0.0017(17)
C12 0.0341(19) 0.0308(19) 0.0371(18) 0.0023(15) 0.0100(14) 0.0049(15)
C13 0.0238(16) 0.0258(16) 0.0260(16) 0.0015(12) 0.0074(13) -0.0004(13)
C14 0.0276(17) 0.0190(16) 0.0346(18) -0.0026(12) 0.0076(13) 0.0053(12)
C15 0.0239(17) 0.0210(16) 0.0342(18) -0.0030(13) 0.0052(13) 0.0004(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 106.4(3) yes
O1 C1 C3 112.0(3) yes
O1 C1 C6 107.7(2) yes
C2 C1 C3 109.6(3) yes
C2 C1 C6 109.5(3) yes
C3 C1 C6 111.6(3) yes
Cl1 C2 Cl2 107.47(15) yes
Cl1 C2 Cl3 108.13(15) yes
Cl1 C2 C1 111.53(19) yes
Cl2 C2 Cl3 107.27(16) yes
Cl2 C2 C1 110.58(18) yes
Cl3 C2 C1 111.66(19) yes
C1 C3 C4 117.3(3) yes
O22 C4 C3 121.1(3) yes
O22 C4 C5 122.7(3) yes
C3 C4 C5 115.9(3) yes
C1 C6 C7 119.6(3) yes
C1 C6 C15 121.5(3) yes
C7 C6 C15 118.9(3) yes
C6 C7 C8 121.6(3) yes
C7 C8 C9 122.5(3) yes
C7 C8 C13 119.2(3) yes
C9 C8 C13 118.3(3) yes
C8 C9 C10 121.3(3) yes
C9 C10 C11 120.0(3) yes
C10 C11 C12 120.6(3) yes
C11 C12 C13 121.2(3) yes
C8 C13 C12 118.6(3) yes
C8 C13 C14 118.5(3) yes
C12 C13 C14 122.8(3) yes
C13 C14 C15 120.4(3) yes
C6 C15 C14 121.2(3) yes
C1 O1 H1 109.216 no
C1 C3 H2 108.786 no
C1 C3 H3 108.650 no
C4 C3 H2 106.268 no
C4 C3 H3 106.169 no
H2 C3 H3 109.433 no
C4 C5 H4 109.573 no
C4 C5 H5 109.945 no
C4 C5 H6 108.977 no
H4 C5 H5 109.442 no
H4 C5 H6 109.442 no
H5 C5 H6 109.447 no
C6 C7 H7 119.241 no
C8 C7 H7 119.160 no
C8 C9 H8 119.233 no
C10 C9 H8 119.485 no
C9 C10 H9 119.989 no
C11 C10 H9 120.050 no
C10 C11 H10 119.718 no
C12 C11 H10 119.685 no
C11 C12 H11 119.358 no
C13 C12 H11 119.480 no
C13 C14 H12 119.823 no
C15 C14 H12 119.734 no
C6 C15 H13 119.567 no
C14 C15 H13 119.187 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 1.778(3) yes
Cl2 C2 1.772(3) yes
Cl3 C2 1.768(3) yes
O1 C1 1.400(4) yes
O22 C4 1.208(5) yes
C1 C2 1.571(4) yes
C1 C3 1.548(4) yes
C1 C6 1.525(4) yes
C3 C4 1.520(4) yes
C4 C5 1.488(5) yes
C6 C7 1.367(4) yes
C6 C15 1.418(4) yes
C7 C8 1.404(4) yes
C8 C9 1.413(4) yes
C8 C13 1.423(4) yes
C9 C10 1.368(4) yes
C10 C11 1.389(5) yes
C11 C12 1.365(5) yes
C12 C13 1.405(4) yes
C13 C14 1.418(4) yes
C14 C15 1.362(4) yes
O1 H1 0.852 no
C3 H2 0.970 no
C3 H3 0.970 no
C5 H4 0.960 no
C5 H5 0.960 no
C5 H6 0.960 no
C7 H7 0.930 no
C9 H8 0.930 no
C10 H9 0.930 no
C11 H10 0.930 no
C12 H11 0.930 no
C14 H12 0.930 no
C15 H13 0.930 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
Cl1 C3 3.197(4) no .
Cl1 C6 3.138(3) no .
Cl1 C15 3.306(4) no .
Cl2 O1 3.061(3) no .
Cl2 O22 3.330(3) no .
Cl2 C3 3.090(4) no .
Cl2 C4 3.044(4) no .
Cl3 O1 2.963(3) no .
Cl3 C6 3.162(3) no .
Cl3 C7 3.206(4) no .
O1 O22 2.642(3) no .
O1 C4 2.886(4) no .
O1 C7 2.696(4) no .
O22 C1 2.983(4) no .
C2 C4 3.340(5) no .
C2 C7 3.300(4) no .
C2 C15 3.412(5) no .
C3 C15 2.915(4) no .
C6 C13 2.816(4) no .
C7 C14 2.786(4) no .
C8 C11 2.795(4) no .
C8 C15 2.789(4) no .
C9 C12 2.767(5) no .
C10 C13 2.799(4) no .
Cl1 Cl3 3.5735(19) no 1_565
Cl1 O1 3.181(3) no 1_565
Cl2 Cl2 3.4294(18) no 2_646
Cl2 Cl2 3.4294(18) no 2_656
Cl3 Cl1 3.5735(19) no 1_545
Cl3 O22 3.363(3) no 1_455
Cl3 C4 3.527(4) no 1_455
Cl3 C5 3.589(4) no 1_455
O1 Cl1 3.181(3) no 1_545
O22 Cl3 3.363(3) no 1_655
C4 Cl3 3.527(4) no 1_655
C5 Cl3 3.589(4) no 1_655
C8 C14 3.484(5) no 2_645
C9 C13 3.515(5) no 2_545
C9 C14 3.551(4) no 1_545
C13 C9 3.515(5) no 2_555
C14 C8 3.484(5) no 2_655
C14 C9 3.551(4) no 1_565
Cl1 H3 2.6619 no .
Cl1 H13 3.0825 no .
Cl2 H1 2.8741 no .
Cl2 H3 3.0833 no .
Cl2 H6 3.4783 no .
Cl3 H1 3.4776 no .
Cl3 H7 2.9036 no .
O1 H2 2.8283 no .
O1 H3 3.2219 no .
O1 H7 2.3720 no .
O22 H1 1.8980 no .
O22 H2 2.7468 no .
O22 H3 3.0958 no .
O22 H4 2.6423 no .
O22 H5 3.1265 no .
O22 H6 2.6384 no .
C1 H7 2.6255 no .
C1 H13 2.7178 no .
C2 H1 2.7039 no .
C2 H2 3.3527 no .
C2 H3 2.5666 no .
C2 H7 3.3037 no .
C2 H13 3.4631 no .
C3 H1 2.4210 no .
C3 H4 3.1392 no .
C3 H5 2.5253 no .
C3 H6 3.1943 no .
C3 H13 2.6010 no .
C4 H1 2.3824 no .
C5 H2 2.9472 no .
C5 H3 2.5213 no .
C6 H1 3.0789 no .
C6 H2 2.5693 no .
C6 H3 2.8976 no .
C6 H12 3.2590 no .
C7 H1 3.5352 no .
C7 H8 2.6469 no .
C7 H13 3.2344 no .
C8 H9 3.2613 no .
C8 H11 3.2726 no .
C8 H12 3.2841 no .
C9 H7 2.6432 no .
C9 H10 3.2229 no .
C10 H11 3.2273 no .
C11 H8 3.2247 no .
C12 H9 3.2280 no .
C12 H12 2.6688 no .
C13 H7 3.2756 no .
C13 H8 3.2742 no .
C13 H10 3.2488 no .
C13 H13 3.2494 no .
C14 H11 2.6593 no .
C15 H2 2.6833 no .
C15 H3 2.9515 no .
C15 H7 3.2399 no .
H1 H2 2.8745 no .
H1 H3 3.2378 no .
H1 H7 3.2074 no .
H2 H4 3.2832 no .
H2 H5 2.8959 no .
H2 H13 2.3769 no .
H3 H4 3.2264 no .
H3 H5 2.1553 no .
H3 H6 3.1168 no .
H3 H13 2.3977 no .
H7 H8 2.4836 no .
H8 H9 2.2901 no .
H9 H10 2.3161 no .
H10 H11 2.2814 no .
H11 H12 2.5140 no .
H12 H13 2.2767 no .
Cl1 H1 3.3026 no 1_565
Cl1 H4 3.2626 no 1_455
Cl1 H9 3.2880 no 2_555
Cl1 H10 3.2246 no 2_555
Cl2 H5 3.4940 no 2_646
Cl2 H6 3.4976 no 2_646
Cl3 H4 2.8445 no 1_455
Cl3 H6 3.2769 no 2_646
Cl3 H9 3.0752 no 2_555
Cl3 H10 3.0167 no 2_545
O1 H3 3.1970 no 1_545
O1 H11 3.0964 no 2_645
O1 H13 3.0134 no 1_545
O22 H4 3.2822 no 2_746
O22 H5 3.0500 no 1_545
O22 H6 3.2289 no 2_746
O22 H10 3.2620 no 2_645
O22 H11 3.3767 no 2_645
C1 H11 3.3884 no 2_645
C2 H4 3.4771 no 1_455
C3 H11 3.2003 no 2_645
C4 H11 3.5668 no 2_645
C6 H9 3.3486 no 2_555
C6 H11 3.4441 no 2_645
C6 H12 3.1976 no 2_645
C7 H9 3.2249 no 2_555
C7 H12 3.3821 no 1_545
C7 H12 3.1489 no 2_645
C7 H13 3.5885 no 1_545
C8 H8 3.0503 no 2_555
C8 H9 3.3141 no 2_555
C8 H12 3.3443 no 1_545
C8 H12 3.0703 no 2_645
C8 H13 3.5967 no 2_645
C9 H2 3.5541 no 2_645
C9 H8 3.0326 no 2_555
C9 H11 3.4746 no 1_545
C9 H12 2.9944 no 1_545
C10 H2 2.9304 no 2_645
C10 H8 3.1023 no 2_555
C10 H11 3.4453 no 1_545
C11 H2 3.0904 no 2_645
C11 H7 3.5199 no 2_555
C11 H8 3.1905 no 2_555
C11 H13 3.4096 no 2_645
C12 H2 3.4804 no 2_655
C12 H8 3.4466 no 1_565
C12 H8 3.1905 no 2_555
C12 H13 3.2203 no 2_645
C13 H8 3.3767 no 1_565
C13 H8 3.1012 no 2_555
C13 H9 3.5387 no 2_555
C13 H12 3.0110 no 2_645
C13 H13 3.3459 no 2_645
C14 H7 3.3637 no 1_565
C14 H8 2.9916 no 1_565
C14 H12 3.0329 no 2_645
C15 H7 3.3178 no 1_565
C15 H9 3.5489 no 2_555
C15 H12 3.1394 no 2_645
H1 Cl1 3.3026 no 1_545
H1 H3 2.8766 no 1_545
H1 H5 3.3718 no 1_545
H1 H11 3.1639 no 2_645
H1 H13 3.3045 no 1_545
H2 C9 3.5541 no 2_655
H2 C10 2.9304 no 2_655
H2 C11 3.0904 no 2_655
H2 C12 3.4804 no 2_645
H2 H9 2.9228 no 2_655
H2 H10 3.1905 no 2_655
H2 H11 2.5529 no 2_645
H3 O1 3.1970 no 1_565
H3 H1 2.8766 no 1_565
H3 H10 3.4897 no 2_655
H4 Cl1 3.2626 no 1_655
H4 Cl3 2.8445 no 1_655
H4 O22 3.2822 no 2_756
H4 C2 3.4771 no 1_655
H4 H5 3.2927 no 2_746
H4 H6 3.4534 no 2_746
H4 H6 3.3621 no 2_756
H5 Cl2 3.4940 no 2_656
H5 O22 3.0500 no 1_565
H5 H1 3.3718 no 1_565
H5 H4 3.2927 no 2_756
H5 H6 3.2376 no 2_756
H5 H10 3.2324 no 2_655
H6 Cl2 3.4976 no 2_656
H6 Cl3 3.2769 no 2_656
H6 O22 3.2289 no 2_756
H6 H4 3.3621 no 2_746
H6 H4 3.4534 no 2_756
H6 H5 3.2376 no 2_746
H7 C11 3.5199 no 2_545
H7 C14 3.3637 no 1_545
H7 C15 3.3178 no 1_545
H7 H9 3.5991 no 2_555
H7 H10 3.4171 no 2_545
H7 H12 3.0532 no 1_545
H7 H13 2.9314 no 1_545
H8 C8 3.0503 no 2_545
H8 C9 3.0326 no 2_545
H8 C10 3.1023 no 2_545
H8 C11 3.1905 no 2_545
H8 C12 3.4466 no 1_545
H8 C12 3.1905 no 2_545
H8 C13 3.3767 no 1_545
H8 C13 3.1012 no 2_545
H8 C14 2.9916 no 1_545
H8 H8 3.5070 no 2_545
H8 H8 3.5070 no 2_555
H8 H11 3.1724 no 1_545
H8 H12 2.6528 no 1_545
H9 Cl1 3.2880 no 2_545
H9 Cl3 3.0752 no 2_545
H9 C6 3.3486 no 2_545
H9 C7 3.2249 no 2_545
H9 C8 3.3141 no 2_545
H9 C13 3.5387 no 2_545
H9 C15 3.5489 no 2_545
H9 H2 2.9228 no 2_645
H9 H7 3.5991 no 2_545
H9 H11 3.1180 no 1_545
H10 Cl1 3.2246 no 2_545
H10 Cl3 3.0167 no 2_555
H10 O22 3.2620 no 2_655
H10 H2 3.1905 no 2_645
H10 H3 3.4897 no 2_645
H10 H5 3.2324 no 2_645
H10 H7 3.4171 no 2_555
H11 O1 3.0964 no 2_655
H11 O22 3.3767 no 2_655
H11 C1 3.3884 no 2_655
H11 C3 3.2003 no 2_655
H11 C4 3.5668 no 2_655
H11 C6 3.4441 no 2_655
H11 C9 3.4746 no 1_565
H11 C10 3.4453 no 1_565
H11 H1 3.1639 no 2_655
H11 H2 2.5529 no 2_655
H11 H8 3.1724 no 1_565
H11 H9 3.1180 no 1_565
H11 H13 3.5232 no 2_645
H12 C6 3.1976 no 2_655
H12 C7 3.3821 no 1_565
H12 C7 3.1489 no 2_655
H12 C8 3.3443 no 1_565
H12 C8 3.0703 no 2_655
H12 C9 2.9944 no 1_565
H12 C13 3.0110 no 2_655
H12 C14 3.0329 no 2_655
H12 C15 3.1394 no 2_655
H12 H7 3.0532 no 1_565
H12 H8 2.6528 no 1_565
H12 H12 3.5041 no 2_645
H12 H12 3.5041 no 2_655
H13 O1 3.0134 no 1_565
H13 C7 3.5885 no 1_565
H13 C8 3.5967 no 2_655
H13 C11 3.4096 no 2_655
H13 C12 3.2203 no 2_655
H13 C13 3.3459 no 2_655
H13 H1 3.3045 no 1_565
H13 H7 2.9314 no 1_565
H13 H11 3.5232 no 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 Cl1 -175.44(16) no
O1 C1 C2 Cl2 65.0(3) no
O1 C1 C2 Cl3 -54.3(3) no
O1 C1 C3 C4 -35.7(4) no
O1 C1 C6 C7 27.5(4) no
O1 C1 C6 C15 -151.5(3) no
C2 C1 C3 C4 82.1(3) no
C3 C1 C2 Cl1 63.3(3) no
C3 C1 C2 Cl2 -56.2(3) no
C3 C1 C2 Cl3 -175.58(18) no
C2 C1 C6 C7 -87.8(3) no
C2 C1 C6 C15 93.3(3) no
C6 C1 C2 Cl1 -59.4(3) no
C6 C1 C2 Cl2 -178.90(18) no
C6 C1 C2 Cl3 61.7(3) no
C3 C1 C6 C7 150.7(3) no
C3 C1 C6 C15 -28.2(4) no
C6 C1 C3 C4 -156.4(2) no
C1 C3 C4 O22 38.8(5) no
C1 C3 C4 C5 -146.7(3) no
C1 C6 C7 C8 -179.4(2) no
C1 C6 C15 C14 177.8(3) no
C7 C6 C15 C14 -1.2(4) no
C15 C6 C7 C8 -0.4(4) no
C6 C7 C8 C9 -177.3(3) no
C6 C7 C8 C13 1.0(4) no
C7 C8 C9 C10 179.5(3) no
C7 C8 C13 C12 178.6(3) no
C7 C8 C13 C14 -0.0(4) no
C9 C8 C13 C12 -3.1(4) no
C9 C8 C13 C14 178.3(3) no
C13 C8 C9 C10 1.3(4) no
C8 C9 C10 C11 1.0(5) no
C9 C10 C11 C12 -1.4(5) no
C10 C11 C12 C13 -0.5(5) no
C11 C12 C13 C8 2.7(5) no
C11 C12 C13 C14 -178.7(3) no
C8 C13 C14 C15 -1.5(4) no
C12 C13 C14 C15 179.9(3) no
C13 C14 C15 C6 2.1(5) no
|
1502030.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502030.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502030
loop_
_publ_author_name
'\<Duri\<s, Andrej'
'Wiesenganger, Tom\'a\<s'
'Morav\<c\'ikov\'a, Daniela'
'Baran, Peter'
'Ko\<z\'i\<sek, Jozef'
'Da\"ich, Adam'
'Berke\<s, Du\<san'
_publ_section_title
;
Expedient and practical synthesis of CERT-dependent ceramide trafficking
inhibitor HPA-12 and its analogues.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1642
_journal_page_last 1645
_journal_paper_doi 10.1021/ol2001057
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration syn
_chemical_formula_sum 'C19 H26 N O3.5'
_chemical_formula_weight 324.41
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 94.914(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.1137(12)
_cell_length_b 32.608(5)
_cell_length_c 7.7093(13)
_cell_measurement_temperature 298(2)
_cell_volume 1781.7(5)
_computing_cell_refinement 'BRUKER SMART-NT V5.0'
_computing_data_collection 'BRUKER SMART-NT V5.0'
_computing_data_reduction 'BRUKER SAINT-NT V5/6.0'
_computing_molecular_graphics 'BRUKER SHELXTL-NT V5.1'
_computing_publication_material 'BRUKER SHELXTL-NT V5.1'
_computing_structure_refinement 'BRUKER SHELXTL-NT V5.1'
_computing_structure_solution 'BRUKER SHELXTL-NT V5.1'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Bruker AXS SMART CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0358
_diffrn_reflns_av_sigmaI/netI 0.0427
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 36
_diffrn_reflns_limit_k_min -33
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 7810
_diffrn_reflns_theta_full 23.28
_diffrn_reflns_theta_max 23.28
_diffrn_reflns_theta_min 2.50
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type none
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.209
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 700
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.117
_refine_diff_density_min -0.155
_refine_diff_density_rms 0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 1.0(11)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.995
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 436
_refine_ls_number_reflns 4183
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 0.995
_refine_ls_R_factor_all 0.0574
_refine_ls_R_factor_gt 0.0400
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0874
_refine_ls_wR_factor_ref 0.0931
_reflns_number_gt 3295
_reflns_number_total 4183
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2001057_si_003.cif
_cod_data_source_block pba038
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)
_cod_database_code 1502030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3118(3) 0.22586(8) 0.5330(3) 0.0558(6) Uani 1 1 d .
H1O H 0.2627 0.2325 0.6212 0.084 Uiso 1 1 calc R
O2 O 0.4664(3) 0.16326(7) 1.0875(3) 0.0662(7) Uani 1 1 d .
H2O H 0.3858 0.1628 1.1574 0.099 Uiso 1 1 calc R
O3 O 0.9571(3) 0.35730(7) 0.4698(3) 0.0638(7) Uani 1 1 d .
O10 O 0.1728(4) 0.16617(9) 0.3096(3) 0.0789(8) Uani 1 1 d .
H10O H 0.2065 0.1869 0.3920 0.105(16) Uiso 1 1 d R
H20O H 0.1716 0.1393 0.3709 0.15(2) Uiso 1 1 d R
O21 O 1.0739(3) 0.09099(8) 0.4389(3) 0.0640(7) Uani 1 1 d .
H21O H 1.1346 0.0857 0.5314 0.096 Uiso 1 1 calc R
O22 O 1.0024(3) 0.15974(7) 0.9700(3) 0.0559(6) Uani 1 1 d .
H22O H 1.0483 0.1646 1.0690 0.084 Uiso 1 1 calc R
O23 O 0.4490(4) -0.04879(8) 0.4333(4) 0.0793(8) Uani 1 1 d .
N1 N 0.2806(3) 0.23482(8) 0.8821(3) 0.0423(6) Uani 1 1 d D
H1N H 0.2230 0.2118 0.8917 0.032(8) Uiso 1 1 d RD
N21 N 1.1468(3) 0.08856(8) 0.7927(3) 0.0465(7) Uani 1 1 d D
H21N H 1.2036 0.1122 0.8042 0.055(11) Uiso 1 1 d RD
C1 C 0.5088(4) 0.21707(10) 0.5766(4) 0.0451(8) Uani 1 1 d .
H1 H 0.5440 0.1959 0.4951 0.054 Uiso 1 1 calc R
C2 C 0.5401(4) 0.19869(10) 0.7576(4) 0.0434(8) Uani 1 1 d .
H2A H 0.6730 0.1920 0.7789 0.052 Uiso 1 1 calc R
H2B H 0.4706 0.1731 0.7580 0.052 Uiso 1 1 calc R
C3 C 0.4839(4) 0.22484(9) 0.9103(4) 0.0395(7) Uani 1 1 d .
H3 H 0.5542 0.2507 0.9090 0.047 Uiso 1 1 calc R
C4 C 0.5429(4) 0.20328(10) 1.0812(4) 0.0486(8) Uani 1 1 d .
H4A H 0.6795 0.2016 1.0962 0.058 Uiso 1 1 calc R
H4B H 0.5013 0.2193 1.1767 0.058 Uiso 1 1 calc R
C5 C 0.6308(4) 0.25418(10) 0.5480(4) 0.0409(7) Uani 1 1 d .
C6 C 0.5765(5) 0.29324(10) 0.5915(4) 0.0493(9) Uani 1 1 d .
H6 H 0.4625 0.2969 0.6402 0.059 Uiso 1 1 calc R
C7 C 0.6873(5) 0.32712(11) 0.5647(5) 0.0548(9) Uani 1 1 d .
H7 H 0.6484 0.3532 0.5950 0.066 Uiso 1 1 calc R
C8 C 0.8574(5) 0.32169(10) 0.4919(4) 0.0470(8) Uani 1 1 d .
C9 C 0.9149(5) 0.28329(10) 0.4489(4) 0.0508(9) Uani 1 1 d .
H9 H 1.0294 0.2796 0.4011 0.061 Uiso 1 1 calc R
C10 C 0.8011(5) 0.24987(11) 0.4772(4) 0.0480(8) Uani 1 1 d .
H10 H 0.8408 0.2238 0.4476 0.058 Uiso 1 1 calc R
C11 C 1.1267(5) 0.35429(13) 0.3863(5) 0.0729(11) Uani 1 1 d .
H11C H 1.2114 0.3357 0.4498 0.109 Uiso 1 1 calc R
H11D H 1.1845 0.3808 0.3828 0.109 Uiso 1 1 calc R
H11E H 1.0989 0.3443 0.2697 0.109 Uiso 1 1 calc R
C12 C 0.2071(4) 0.26465(9) 1.0050(4) 0.0425(8) Uani 1 1 d .
H12 H 0.2380 0.2545 1.1237 0.051 Uiso 1 1 calc R
C13 C -0.0064(4) 0.26560(11) 0.9705(5) 0.0572(10) Uani 1 1 d .
H13A H -0.0577 0.2852 1.0463 0.086 Uiso 1 1 calc R
H13B H -0.0567 0.2389 0.9918 0.086 Uiso 1 1 calc R
H13C H -0.0396 0.2732 0.8515 0.086 Uiso 1 1 calc R
C14 C 0.3002(4) 0.30594(10) 0.9891(4) 0.0415(8) Uani 1 1 d .
C15 C 0.4508(5) 0.31757(11) 1.1048(5) 0.0582(9) Uani 1 1 d .
H15 H 0.4954 0.2995 1.1924 0.070 Uiso 1 1 calc R
C16 C 0.5357(6) 0.35537(13) 1.0925(6) 0.0765(12) Uani 1 1 d .
H16 H 0.6369 0.3625 1.1712 0.092 Uiso 1 1 calc R
C17 C 0.4726(6) 0.38247(13) 0.9658(6) 0.0766(12) Uani 1 1 d .
H17 H 0.5299 0.4080 0.9585 0.092 Uiso 1 1 calc R
C18 C 0.3246(6) 0.37186(11) 0.8494(5) 0.0658(10) Uani 1 1 d .
H18 H 0.2825 0.3900 0.7615 0.079 Uiso 1 1 calc R
C19 C 0.2365(5) 0.33390(11) 0.8623(4) 0.0525(9) Uani 1 1 d .
H19 H 0.1337 0.3273 0.7847 0.063 Uiso 1 1 calc R
C21 C 0.8809(5) 0.09783(10) 0.4689(4) 0.0512(9) Uani 1 1 d .
H21 H 0.8283 0.1162 0.3766 0.061 Uiso 1 1 calc R
C22 C 0.8667(4) 0.12020(10) 0.6409(4) 0.0463(8) Uani 1 1 d .
H22A H 0.7348 0.1264 0.6520 0.056 Uiso 1 1 calc R
H22B H 0.9327 0.1461 0.6357 0.056 Uiso 1 1 calc R
C23 C 0.9446(4) 0.09760(9) 0.8047(4) 0.0416(8) Uani 1 1 d .
H23 H 0.8781 0.0713 0.8079 0.050 Uiso 1 1 calc R
C24 C 0.9054(4) 0.12134(9) 0.9677(4) 0.0463(8) Uani 1 1 d .
H24A H 0.7708 0.1260 0.9689 0.056 Uiso 1 1 calc R
H24B H 0.9477 0.1056 1.0704 0.056 Uiso 1 1 calc R
C25 C 0.7659(5) 0.05894(10) 0.4544(4) 0.0472(8) Uani 1 1 d .
C26 C 0.8385(5) 0.02132(12) 0.5085(5) 0.0646(10) Uani 1 1 d .
H26 H 0.9641 0.0196 0.5525 0.077 Uiso 1 1 calc R
C27 C 0.7305(6) -0.01349(12) 0.4991(5) 0.0681(11) Uani 1 1 d .
H27 H 0.7841 -0.0383 0.5362 0.082 Uiso 1 1 calc R
C28 C 0.5441(5) -0.01227(12) 0.4359(4) 0.0570(9) Uani 1 1 d .
C29 C 0.4676(5) 0.02446(12) 0.3820(5) 0.0618(10) Uani 1 1 d .
H29 H 0.3417 0.0260 0.3388 0.074 Uiso 1 1 calc R
C30 C 0.5785(5) 0.05952(11) 0.3921(5) 0.0584(9) Uani 1 1 d .
H30 H 0.5244 0.0843 0.3554 0.070 Uiso 1 1 calc R
C31 C 0.2635(6) -0.04972(13) 0.3510(6) 0.0812(12) Uani 1 1 d .
H31C H 0.1864 -0.0303 0.4062 0.122 Uiso 1 1 calc R
H31D H 0.2118 -0.0767 0.3606 0.122 Uiso 1 1 calc R
H31E H 0.2663 -0.0427 0.2303 0.122 Uiso 1 1 calc R
C32 C 1.2397(4) 0.06181(10) 0.9301(4) 0.0466(8) Uani 1 1 d .
H32 H 1.2224 0.0742 1.0435 0.056 Uiso 1 1 calc R
C33 C 1.4490(5) 0.06162(13) 0.9057(5) 0.0697(11) Uani 1 1 d .
H33A H 1.4676 0.0536 0.7885 0.104 Uiso 1 1 calc R
H33B H 1.5122 0.0425 0.9855 0.104 Uiso 1 1 calc R
H33C H 1.4999 0.0886 0.9276 0.104 Uiso 1 1 calc R
C34 C 1.1505(5) 0.01966(11) 0.9255(4) 0.0465(8) Uani 1 1 d .
C35 C 1.0034(5) 0.01101(11) 1.0283(5) 0.0595(10) Uani 1 1 d .
H35 H 0.9637 0.0312 1.1021 0.071 Uiso 1 1 calc R
C36 C 0.9155(6) -0.02652(12) 1.0233(6) 0.0730(12) Uani 1 1 d .
H36 H 0.8151 -0.0312 1.0905 0.088 Uiso 1 1 calc R
C37 C 0.9751(7) -0.05695(13) 0.9200(6) 0.0785(13) Uani 1 1 d .
H37 H 0.9162 -0.0824 0.9174 0.094 Uiso 1 1 calc R
C38 C 1.1228(6) -0.04985(12) 0.8196(5) 0.0694(11) Uani 1 1 d .
H38 H 1.1647 -0.0707 0.7502 0.083 Uiso 1 1 calc R
C39 C 1.2093(5) -0.01167(12) 0.8216(5) 0.0605(10) Uani 1 1 d .
H39 H 1.3080 -0.0071 0.7523 0.073 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0433(14) 0.0729(16) 0.0503(13) -0.0089(13) -0.0014(10) 0.0027(11)
O2 0.0751(18) 0.0550(15) 0.0726(18) 0.0150(13) 0.0304(13) 0.0016(13)
O3 0.0660(17) 0.0569(16) 0.0715(17) 0.0045(13) 0.0226(13) -0.0010(13)
O10 0.092(2) 0.095(2) 0.0512(15) -0.0104(16) 0.0149(13) -0.0415(16)
O21 0.0567(16) 0.0809(19) 0.0572(15) 0.0002(14) 0.0208(12) 0.0025(13)
O22 0.0611(16) 0.0493(14) 0.0570(14) -0.0092(12) 0.0029(12) -0.0126(12)
O23 0.082(2) 0.0582(18) 0.093(2) 0.0005(15) -0.0186(16) -0.0037(14)
N1 0.0370(15) 0.0406(17) 0.0497(16) -0.0088(12) 0.0071(12) -0.0063(12)
N21 0.0424(16) 0.0456(17) 0.0524(17) 0.0030(13) 0.0100(13) -0.0015(13)
C1 0.045(2) 0.049(2) 0.0407(19) -0.0083(16) 0.0031(15) 0.0040(16)
C2 0.0440(19) 0.0382(18) 0.048(2) -0.0027(15) 0.0065(15) 0.0015(14)
C3 0.0359(18) 0.0399(18) 0.0433(19) -0.0019(15) 0.0068(13) -0.0026(14)
C4 0.0441(19) 0.053(2) 0.050(2) 0.0009(17) 0.0101(15) 0.0015(16)
C5 0.043(2) 0.050(2) 0.0304(16) -0.0030(15) 0.0043(14) 0.0078(16)
C6 0.049(2) 0.055(2) 0.045(2) 0.0000(17) 0.0143(15) 0.0116(17)
C7 0.065(3) 0.045(2) 0.057(2) -0.0034(17) 0.0176(18) 0.0105(19)
C8 0.055(2) 0.048(2) 0.0394(18) 0.0042(15) 0.0086(16) 0.0060(17)
C9 0.046(2) 0.059(2) 0.050(2) 0.0067(18) 0.0146(16) 0.0089(18)
C10 0.053(2) 0.046(2) 0.0449(19) -0.0001(16) 0.0069(16) 0.0138(17)
C11 0.065(3) 0.082(3) 0.074(3) 0.012(2) 0.021(2) -0.006(2)
C12 0.0420(19) 0.045(2) 0.0414(18) -0.0059(15) 0.0085(15) 0.0002(15)
C13 0.045(2) 0.059(2) 0.069(2) -0.0126(19) 0.0138(18) -0.0044(16)
C14 0.0423(19) 0.0447(19) 0.0386(18) -0.0085(16) 0.0109(15) 0.0051(15)
C15 0.059(2) 0.055(2) 0.058(2) -0.0042(18) -0.0063(18) -0.0030(18)
C16 0.074(3) 0.061(3) 0.091(3) -0.008(3) -0.010(2) -0.015(2)
C17 0.080(3) 0.055(3) 0.097(3) -0.011(3) 0.023(3) -0.017(2)
C18 0.089(3) 0.046(2) 0.065(2) 0.0011(19) 0.017(2) 0.010(2)
C19 0.059(2) 0.052(2) 0.047(2) -0.0070(18) 0.0047(16) 0.0031(18)
C21 0.053(2) 0.057(2) 0.044(2) 0.0001(17) 0.0082(15) 0.0086(17)
C22 0.047(2) 0.0453(19) 0.047(2) 0.0006(17) 0.0059(15) 0.0038(15)
C23 0.0403(18) 0.0390(18) 0.046(2) -0.0030(15) 0.0097(14) -0.0035(14)
C24 0.0434(19) 0.047(2) 0.050(2) -0.0062(16) 0.0112(15) -0.0047(16)
C25 0.057(2) 0.050(2) 0.0341(18) -0.0021(17) 0.0040(15) 0.0093(18)
C26 0.056(2) 0.060(2) 0.075(3) -0.012(2) -0.0119(19) 0.009(2)
C27 0.076(3) 0.049(2) 0.075(3) -0.005(2) -0.018(2) 0.015(2)
C28 0.070(3) 0.050(2) 0.049(2) -0.0044(18) -0.0054(19) 0.003(2)
C29 0.053(2) 0.062(3) 0.068(3) -0.001(2) -0.0081(18) 0.006(2)
C30 0.065(3) 0.049(2) 0.060(2) 0.0043(19) -0.0012(18) 0.0145(19)
C31 0.082(3) 0.069(3) 0.092(3) -0.002(2) 0.000(2) -0.006(2)
C32 0.0387(19) 0.053(2) 0.049(2) 0.0012(17) 0.0047(15) -0.0003(15)
C33 0.046(2) 0.073(3) 0.089(3) 0.003(2) 0.0055(19) -0.0014(19)
C34 0.046(2) 0.0459(19) 0.046(2) 0.0044(16) -0.0017(16) 0.0010(16)
C35 0.064(2) 0.052(3) 0.064(2) 0.0020(18) 0.0116(19) -0.0024(19)
C36 0.077(3) 0.063(3) 0.080(3) 0.011(2) 0.014(2) -0.016(2)
C37 0.101(4) 0.053(3) 0.079(3) 0.008(2) -0.005(3) -0.023(2)
C38 0.093(3) 0.050(3) 0.064(3) -0.006(2) -0.004(2) 0.007(2)
C39 0.070(3) 0.053(2) 0.059(2) 0.000(2) 0.0077(19) 0.0039(19)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O3 C11 117.7(3)
C28 O23 C31 117.8(3)
C3 N1 C12 116.3(2)
C23 N21 C32 116.6(2)
O1 C1 C5 111.4(3)
O1 C1 C2 110.9(3)
C5 C1 C2 114.1(2)
C1 C2 C3 117.3(3)
N1 C3 C4 115.0(2)
N1 C3 C2 109.0(2)
C4 C3 C2 109.7(3)
O2 C4 C3 112.2(3)
C10 C5 C6 117.6(3)
C10 C5 C1 120.7(3)
C6 C5 C1 121.7(3)
C5 C6 C7 121.7(3)
C6 C7 C8 119.1(3)
C9 C8 O3 125.0(3)
C9 C8 C7 120.3(3)
O3 C8 C7 114.7(3)
C8 C9 C10 119.4(3)
C5 C10 C9 121.8(3)
N1 C12 C14 110.6(2)
N1 C12 C13 107.6(2)
C14 C12 C13 114.0(3)
C19 C14 C15 117.5(3)
C19 C14 C12 121.7(3)
C15 C14 C12 120.8(3)
C16 C15 C14 121.2(3)
C17 C16 C15 120.6(4)
C16 C17 C18 119.5(4)
C17 C18 C19 120.2(4)
C14 C19 C18 120.9(3)
O21 C21 C25 112.3(3)
O21 C21 C22 110.6(3)
C25 C21 C22 113.0(3)
C21 C22 C23 116.3(3)
N21 C23 C24 113.7(2)
N21 C23 C22 109.3(2)
C24 C23 C22 111.0(3)
O22 C24 C23 109.5(3)
C30 C25 C26 116.3(3)
C30 C25 C21 121.1(3)
C26 C25 C21 122.6(3)
C27 C26 C25 121.8(3)
C26 C27 C28 121.0(4)
C29 C28 O23 125.1(3)
C29 C28 C27 118.8(4)
O23 C28 C27 116.2(3)
C28 C29 C30 119.7(3)
C25 C30 C29 122.5(3)
N21 C32 C34 110.9(3)
N21 C32 C33 107.2(3)
C34 C32 C33 114.0(3)
C39 C34 C35 117.3(3)
C39 C34 C32 122.5(3)
C35 C34 C32 120.3(3)
C36 C35 C34 121.8(4)
C37 C36 C35 120.1(4)
C36 C37 C38 119.8(4)
C37 C38 C39 120.2(4)
C34 C39 C38 120.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.442(3)
O2 C4 1.416(4)
O3 C8 1.379(4)
O3 C11 1.419(4)
O21 C21 1.429(4)
O22 C24 1.429(4)
O23 C28 1.369(4)
O23 C31 1.415(5)
N1 C3 1.480(4)
N1 C12 1.484(4)
N21 C23 1.479(4)
N21 C32 1.484(4)
C1 C5 1.516(4)
C1 C2 1.517(4)
C2 C3 1.534(4)
C3 C4 1.521(4)
C5 C10 1.378(4)
C5 C6 1.380(4)
C6 C7 1.383(5)
C7 C8 1.388(5)
C8 C9 1.367(4)
C9 C10 1.386(5)
C12 C14 1.510(4)
C12 C13 1.519(4)
C14 C19 1.384(4)
C14 C15 1.387(4)
C15 C16 1.380(5)
C16 C17 1.364(6)
C17 C18 1.368(5)
C18 C19 1.395(5)
C21 C25 1.508(5)
C21 C22 1.524(4)
C22 C23 1.525(4)
C23 C24 1.522(4)
C25 C30 1.378(4)
C25 C26 1.382(5)
C26 C27 1.369(5)
C27 C28 1.373(5)
C28 C29 1.365(5)
C29 C30 1.388(5)
C32 C34 1.513(5)
C32 C33 1.517(4)
C34 C39 1.385(5)
C34 C35 1.395(5)
C35 C36 1.373(5)
C36 C37 1.362(6)
C37 C38 1.377(6)
C38 C39 1.388(5)
|
1502031.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502031.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502031
loop_
_publ_author_name
'\<Duri\<s, Andrej'
'Wiesenganger, Tom\'a\<s'
'Morav\<c\'ikov\'a, Daniela'
'Baran, Peter'
'Ko\<z\'i\<sek, Jozef'
'Da\"ich, Adam'
'Berke\<s, Du\<san'
_publ_section_title
;
Expedient and practical synthesis of CERT-dependent ceramide trafficking
inhibitor HPA-12 and its analogues.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1642
_journal_page_last 1645
_journal_paper_doi 10.1021/ol2001057
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration syn
_chemical_formula_moiety 'C13 H20 N O4'
_chemical_formula_sum 'C13 H20 N O4'
_chemical_formula_weight 254.30
_chemical_name_systematic
;
?
;
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 98.117(4)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 7.7687(3)
_cell_length_b 6.0916(2)
_cell_length_c 14.9497(6)
_cell_measurement_reflns_used 18522
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 29.2784
_cell_measurement_theta_min 3.5338
_cell_volume 700.39(5)
_computing_cell_refinement 'CrysAlis CCD'
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics 'DIAMOND (Brandenburg, 1998)'
_computing_publication_material ' enCIFer (Allen et al., 2004)'
_computing_structure_refinement
'G. M. Sheldrick, Acta Cryst., A46 (2008) 112.'
_computing_structure_solution
'G. M. Sheldrick, Acta Cryst., A46 (2008) 112.'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Goniometer Xcalibur, CCD: Ruby (Gemini Mo)'
_diffrn_measurement_method
;
Rotation method data acquisition using \w and \f scans
;
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0208
_diffrn_reflns_av_sigmaI/netI 0.0098
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 28447
_diffrn_reflns_theta_full 26.37
_diffrn_reflns_theta_max 26.37
_diffrn_reflns_theta_min 4.08
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_T_max 0.975
_exptl_absorpt_correction_T_min 0.943
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.206
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 274
_exptl_crystal_size_max 0.982
_exptl_crystal_size_mid 0.442
_exptl_crystal_size_min 0.340
_refine_diff_density_max 0.730
_refine_diff_density_min -0.450
_refine_diff_density_rms 0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0(3)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.120
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 161
_refine_ls_number_reflns 2854
_refine_ls_number_restraints 137
_refine_ls_restrained_S_all 1.508
_refine_ls_R_factor_all 0.0743
_refine_ls_R_factor_gt 0.0693
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1291P)^2^+0.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2060
_refine_ls_wR_factor_ref 0.2115
_reflns_number_gt 2554
_reflns_number_total 2854
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2001057_si_003.cif
_cod_data_source_block I
_cod_original_sg_symbol_H-M 'P 21'
_cod_database_code 1502031
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8664(5) 0.5999(7) 0.2706(3) 0.0445(9) Uani 1 1 d U . .
H1A H 0.9072 0.7168 0.3134 0.053 Uiso 1 1 calc R . .
C2 C 0.7074(5) 0.4905(8) 0.3015(3) 0.0464(9) Uani 1 1 d U . .
H2A H 0.6931 0.3457 0.2745 0.056 Uiso 1 1 calc R . .
H2B H 0.6049 0.5757 0.2791 0.056 Uiso 1 1 calc R . .
C3 C 0.7177(4) 0.4673(2) 0.40468(18) 0.0500(9) Uani 1 1 d DU B .
H3A H 0.7373 0.6115 0.4334 0.060 Uiso 1 1 calc R . .
C4 C 0.8600(4) 0.3089(2) 0.44415(18) 0.0790(18) Uani 1 1 d RDU . .
H4B H 0.9701 0.3865 0.4511 0.095 Uiso 0.700(17) 1 d PRD . .
H4A H 0.8387 0.2641 0.5039 0.095 Uiso 1 1 d RD . .
H4C H 0.8681(7) 0.1838(5) 0.4086(3) 0.095 Uiso 0.300(17) 1 d PD A 1
C5 C 0.8199(5) 0.7007(7) 0.1773(3) 0.0447(9) Uani 1 1 d U . .
C6 C 0.7351(7) 0.9008(8) 0.1687(3) 0.0597(11) Uani 1 1 d U . .
H6A H 0.7108 0.9725 0.2204 0.072 Uiso 1 1 calc R . .
C7 C 0.6856(7) 0.9969(9) 0.0855(4) 0.0674(13) Uani 1 1 d U . .
H7A H 0.6270 1.1304 0.0819 0.081 Uiso 1 1 calc R . .
C8 C 0.7222(6) 0.8971(10) 0.0072(3) 0.0605(11) Uani 1 1 d U . .
C9 C 0.8079(7) 0.6967(10) 0.0156(3) 0.0663(14) Uani 1 1 d U . .
H9A H 0.8336 0.6258 -0.0360 0.080 Uiso 1 1 calc R . .
C10 C 0.8559(6) 0.6001(9) 0.0991(3) 0.0554(10) Uani 1 1 d U . .
H10 H 0.9132 0.4657 0.1027 0.067 Uiso 1 1 calc R . .
C11 C 0.6703(8) 1.0023(15) -0.0838(4) 0.0872(19) Uani 1 1 d U . .
H11C H 0.6123 1.1388 -0.0763 0.105 Uiso 1 1 calc R . .
H11B H 0.5934 0.9061 -0.1213 0.105 Uiso 1 1 calc R . .
H11A H 0.7723 1.0291 -0.1117 0.105 Uiso 1 1 calc R . .
C12 C 0.3408(5) 0.8503(7) 0.3330(3) 0.0442(9) Uani 1 1 d U . .
C13 C 0.2628(7) 0.9849(10) 0.2533(3) 0.0692(14) Uani 1 1 d U . .
H13C H 0.3085 1.1315 0.2592 0.083 Uiso 1 1 calc R . .
H13B H 0.1388 0.9893 0.2511 0.083 Uiso 1 1 calc R . .
H13A H 0.2914 0.9200 0.1988 0.083 Uiso 1 1 calc R . .
N1 N 0.5509(4) 0.3748(6) 0.4244(2) 0.0454(8) Uani 1 1 d U . .
H1NA H 0.5294 0.2417 0.4009 0.054 Uiso 1 1 d R B .
H1NB H 0.5527 0.3688 0.4841 0.054 Uiso 1 1 d R . .
H1NC H 0.4680 0.4671 0.4007 0.054 Uiso 1 1 d R . .
O1 O 1.0018(2) 0.4380(2) 0.27224(12) 0.0582(8) Uani 1 1 d U . .
H1W H 1.1111 0.4962 0.2884 0.087 Uiso 1 1 d R . .
O2 O 0.8792(2) 0.1180(2) 0.39502(12) 0.094(3) Uani 0.700(17) 1 d PRDU B .
O3 O 0.4515(2) 0.9353(2) 0.39078(12) 0.0603(9) Uani 1 1 d RU . .
O4 O 0.2972(2) 0.6511(2) 0.33654(12) 0.0592(9) Uani 1 1 d RU . .
O5 O 1.0384(6) 0.3655(19) 0.4654(5) 0.094(3) Uani 0.05 1 d PDU B 1
O6 O 1.0411(6) 0.299(3) 0.4397(11) 0.094(3) Uani 0.25 1 d PDU B 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0396(18) 0.0388(19) 0.053(2) -0.0053(16) 0.0002(15) 0.0017(15)
C2 0.0400(17) 0.052(2) 0.0450(19) -0.0041(17) -0.0013(14) 0.0027(16)
C3 0.051(2) 0.054(2) 0.042(2) -0.0017(17) -0.0018(15) 0.0028(19)
C4 0.078(3) 0.108(5) 0.047(2) 0.000(3) -0.006(2) 0.036(3)
C5 0.0376(17) 0.042(2) 0.053(2) -0.0030(16) 0.0018(15) -0.0037(15)
C6 0.074(3) 0.044(2) 0.059(2) -0.005(2) 0.004(2) 0.010(2)
C7 0.077(3) 0.051(3) 0.072(3) 0.008(2) 0.004(2) 0.010(2)
C8 0.056(2) 0.068(3) 0.058(2) 0.009(2) 0.0081(19) -0.006(2)
C9 0.067(3) 0.082(4) 0.052(2) -0.003(2) 0.013(2) 0.010(3)
C10 0.054(2) 0.051(2) 0.063(3) -0.001(2) 0.0115(19) 0.010(2)
C11 0.081(4) 0.113(5) 0.067(3) 0.024(3) 0.007(3) 0.002(4)
C12 0.0458(19) 0.044(2) 0.0429(19) 0.0009(15) 0.0059(15) 0.0070(16)
C13 0.076(3) 0.064(3) 0.063(3) 0.011(2) -0.005(2) 0.013(3)
N1 0.0554(18) 0.0398(17) 0.0396(15) 0.0007(13) 0.0018(13) 0.0034(14)
O1 0.0438(15) 0.0505(17) 0.078(2) 0.0044(16) 0.0018(13) 0.0062(13)
O2 0.110(5) 0.068(4) 0.092(4) -0.012(3) -0.025(3) 0.034(3)
O3 0.076(2) 0.0530(18) 0.0490(16) -0.0018(14) -0.0011(14) -0.0115(16)
O4 0.0442(15) 0.0509(18) 0.078(2) 0.0067(15) -0.0063(13) 0.0007(13)
O5 0.110(5) 0.068(4) 0.092(4) -0.012(3) -0.025(3) 0.034(3)
O6 0.110(5) 0.068(4) 0.092(4) -0.012(3) -0.025(3) 0.034(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C5 111.8(3)
O1 C1 C2 108.4(3)
C5 C1 C2 110.8(3)
O1 C1 H1A 108.6
C5 C1 H1A 108.6
C2 C1 H1A 108.6
C1 C2 C3 114.3(3)
C1 C2 H2A 108.7
C3 C2 H2A 108.7
C1 C2 H2B 108.7
C3 C2 H2B 108.7
H2A C2 H2B 107.6
N1 C3 C4 106.83(17)
N1 C3 C2 108.2(2)
C4 C3 C2 112.27(18)
N1 C3 H3A 109.8
C4 C3 H3A 109.8
C2 C3 H3A 109.8
O2 C4 O6 76.1(8)
O2 C4 O5 98.4(5)
O6 C4 O5 22.7(8)
O2 C4 C3 116.76(14)
O6 C4 C3 132.7(8)
O5 C4 C3 124.4(5)
O2 C4 H4B 107.7
O6 C4 H4B 32.8
O5 C4 H4B 16.2
C3 C4 H4B 108.3
O2 C4 H4A 107.2
O6 C4 H4A 109.3
O5 C4 H4A 98.7
C3 C4 H4A 109.0
H4B C4 H4A 107.5
O2 C4 H4C 3.3(3)
O6 C4 H4C 78.1(8)
O5 C4 H4C 100.5(4)
C3 C4 H4C 113.5(3)
H4B C4 H4C 109.2
H4A C4 H4C 109.2
C6 C5 C10 117.5(4)
C6 C5 C1 119.4(4)
C10 C5 C1 123.1(4)
C7 C6 C5 121.8(5)
C7 C6 H6A 119.1
C5 C6 H6A 119.1
C6 C7 C8 120.8(5)
C6 C7 H7A 119.6
C8 C7 H7A 119.6
C7 C8 C9 117.6(4)
C7 C8 C11 121.1(5)
C9 C8 C11 121.3(5)
C10 C9 C8 121.4(5)
C10 C9 H9A 119.3
C8 C9 H9A 119.3
C9 C10 C5 120.9(4)
C9 C10 H10 119.5
C5 C10 H10 119.5
C8 C11 H11C 109.5
C8 C11 H11B 109.5
H11C C11 H11B 109.5
C8 C11 H11A 109.5
H11C C11 H11A 109.5
H11B C11 H11A 109.5
O3 C12 O4 122.4(3)
O3 C12 C13 119.1(4)
O4 C12 C13 118.5(4)
C12 C13 H13C 109.5
C12 C13 H13B 109.5
H13C C13 H13B 109.5
C12 C13 H13A 109.5
H13C C13 H13A 109.5
H13B C13 H13A 109.5
C3 N1 H1NA 112.9
C3 N1 H1NB 109.0
H1NA N1 H1NB 109.5
C3 N1 H1NC 106.5
H1NA N1 H1NC 109.5
H1NB N1 H1NC 109.5
C1 O1 H1W 112.7
C4 O2 O6 52.6(4)
C4 O2 H4C 6.6(6)
O6 O2 H4C 56.6(7)
O6 O5 C4 78.5(4)
O6 O5 H4B 91.6
C4 O5 H4B 28.9
O5 O6 C4 78.7(5)
O5 O6 O2 128.9(5)
C4 O6 O2 51.3(4)
O5 O6 H4B 44.1
C4 O6 H4B 41.1
O2 O6 H4B 91.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.440(4)
C1 C5 1.520(6)
C1 C2 1.531(6)
C1 H1A 0.9800
C2 C3 1.539(5)
C2 H2A 0.9700
C2 H2B 0.9700
C3 N1 1.481(5)
C3 C4 1.5219
C3 H3A 0.9800
C4 O2 1.3945(12)
C4 O6 1.4189(14)
C4 O5 1.4198(14)
C4 H4B 0.9700
C4 H4A 0.9700
C4 H4C 0.9364(18)
C5 C6 1.383(6)
C5 C10 1.384(6)
C6 C7 1.380(7)
C6 H6A 0.9300
C7 C8 1.383(8)
C7 H7A 0.9300
C8 C9 1.388(8)
C8 C11 1.506(7)
C9 C10 1.382(7)
C9 H9A 0.9300
C10 H10 0.9300
C11 H11C 0.9600
C11 H11B 0.9600
C11 H11A 0.9600
C12 O3 1.242(4)
C12 O4 1.263(5)
C12 C13 1.502(6)
C13 H13C 0.9600
C13 H13B 0.9600
C13 H13A 0.9600
N1 H1NA 0.8901
N1 H1NB 0.8900
N1 H1NC 0.8900
O1 H1W 0.9203
O2 O6 1.735(15)
O2 H4C 0.463(3)
O5 O6 0.56(2)
O5 H4B 0.5577
O6 H4B 0.8007
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 80.4(4)
C5 C1 C2 C3 -156.6(3)
C1 C2 C3 N1 175.9(3)
C1 C2 C3 C4 -66.5(3)
N1 C3 C4 O2 77.8(2)
C2 C3 C4 O2 -40.6(2)
N1 C3 C4 O6 173.6(10)
C2 C3 C4 O6 55.2(10)
N1 C3 C4 O5 -159.2(4)
C2 C3 C4 O5 82.4(4)
O1 C1 C5 C6 -160.0(4)
C2 C1 C5 C6 79.0(5)
O1 C1 C5 C10 21.0(5)
C2 C1 C5 C10 -100.1(5)
C10 C5 C6 C7 0.8(7)
C1 C5 C6 C7 -178.2(4)
C5 C6 C7 C8 -1.2(8)
C6 C7 C8 C9 0.8(8)
C6 C7 C8 C11 -179.3(5)
C7 C8 C9 C10 -0.3(8)
C11 C8 C9 C10 179.9(5)
C8 C9 C10 C5 0.0(8)
C6 C5 C10 C9 -0.3(7)
C1 C5 C10 C9 178.8(4)
O5 C4 O2 O6 -4.4(9)
C3 C4 O2 O6 131.2(7)
O2 C4 O5 O6 11(2)
C3 C4 O5 O6 -120(2)
C4 O5 O6 O2 -11(2)
O2 C4 O6 O5 -169(2)
C3 C4 O6 O5 78(2)
O5 C4 O6 O2 169(2)
C3 C4 O6 O2 -113.8(6)
C4 O2 O6 O5 14(3)
|
1502032.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502032.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502032
loop_
_publ_author_name
'Sun, Christina'
'Lu, Jiasheng'
'Wang, Suning'
_publ_section_title
;
Donor-acceptor assisted alkyne hydration: a luminescent boron-stabilized
enol.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1226
_journal_page_last 1229
_journal_paper_doi 10.1021/ol200106a
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C32 H31 B'
_chemical_formula_weight 426.38
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 65.465(2)
_cell_angle_beta 81.937(2)
_cell_angle_gamma 81.928(2)
_cell_formula_units_Z 2
_cell_length_a 9.3686(14)
_cell_length_b 12.1651(18)
_cell_length_c 12.2768(18)
_cell_measurement_reflns_used 4789
_cell_measurement_temperature 180(2)
_cell_measurement_theta_max 27.47
_cell_measurement_theta_min 2.20
_cell_volume 1255.0(3)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 180(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0235
_diffrn_reflns_av_sigmaI/netI 0.0289
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 13712
_diffrn_reflns_theta_full 27.00
_diffrn_reflns_theta_max 27.00
_diffrn_reflns_theta_min 1.83
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.063
_exptl_absorpt_correction_T_max 0.9969
_exptl_absorpt_correction_T_min 0.9876
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_density_diffrn 1.128
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 456
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.244
_refine_diff_density_min -0.179
_refine_diff_density_rms 0.036
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.037
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 303
_refine_ls_number_reflns 5366
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.037
_refine_ls_R_factor_all 0.0629
_refine_ls_R_factor_gt 0.0462
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+0.2873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1217
_refine_ls_wR_factor_ref 0.1352
_reflns_number_gt 4047
_reflns_number_total 5366
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200106a_si_001.cif
_cod_data_source_block louis25
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C22 C 0.7363(2) 0.06257(19) -0.14203(18) 0.0636(5) Uani 1 1 d .
H22A H 0.8046 0.0965 -0.2132 0.095 Uiso 1 1 calc R
H22B H 0.6377 0.0787 -0.1665 0.095 Uiso 1 1 calc R
H22C H 0.7604 -0.0252 -0.1020 0.095 Uiso 1 1 calc R
C18 C 0.74602(18) 0.12069(14) -0.05655(14) 0.0436(4) Uani 1 1 d .
C19 C 0.63172(17) 0.12361(13) 0.02743(13) 0.0389(3) Uani 1 1 d .
H19A H 0.5453 0.0903 0.0290 0.047 Uiso 1 1 calc R
C20 C 0.63933(15) 0.17377(12) 0.10973(12) 0.0337(3) Uani 1 1 d .
C15 C 0.76647(15) 0.22396(12) 0.10991(12) 0.0329(3) Uani 1 1 d .
C1 C 0.92576(15) 0.24833(12) 0.26750(12) 0.0336(3) Uani 1 1 d .
C6 C 1.00210(15) 0.13242(13) 0.31605(12) 0.0352(3) Uani 1 1 d .
C7 C 0.94566(16) 0.02705(13) 0.31956(13) 0.0384(3) Uani 1 1 d .
C8 C 0.90302(17) -0.06308(13) 0.32412(14) 0.0407(3) Uani 1 1 d .
C9 C 0.85494(16) -0.16943(13) 0.32325(13) 0.0376(3) Uani 1 1 d .
C14 C 0.73035(18) -0.16182(14) 0.26924(15) 0.0457(4) Uani 1 1 d .
H14A H 0.6747 -0.0860 0.2354 0.055 Uiso 1 1 calc R
C13 C 0.68720(18) -0.26350(14) 0.26449(15) 0.0470(4) Uani 1 1 d .
H13A H 0.6023 -0.2571 0.2272 0.056 Uiso 1 1 calc R
C12 C 0.76633(17) -0.37435(14) 0.31340(14) 0.0416(4) Uani 1 1 d .
H12A H 0.7362 -0.4442 0.3101 0.050 Uiso 1 1 calc R
C31 C 0.31603(18) 0.59042(15) 0.34070(17) 0.0505(4) Uani 1 1 d .
H31A H 0.2561 0.5405 0.4115 0.076 Uiso 1 1 calc R
H31B H 0.2558 0.6344 0.2737 0.076 Uiso 1 1 calc R
H31C H 0.3594 0.6486 0.3594 0.076 Uiso 1 1 calc R
C27 C 0.43433(15) 0.50999(13) 0.30607(14) 0.0377(3) Uani 1 1 d .
C26 C 0.49872(16) 0.54633(13) 0.18899(14) 0.0374(3) Uani 1 1 d .
H26A H 0.4665 0.6227 0.1300 0.045 Uiso 1 1 calc R
C25 C 0.60932(15) 0.47385(12) 0.15551(12) 0.0338(3) Uani 1 1 d .
C30 C 0.67845(18) 0.52130(14) 0.02756(13) 0.0433(4) Uani 1 1 d .
H30A H 0.6329 0.6025 -0.0181 0.065 Uiso 1 1 calc R
H30B H 0.6651 0.4666 -0.0097 0.065 Uiso 1 1 calc R
H30C H 0.7821 0.5255 0.0276 0.065 Uiso 1 1 calc R
C24 C 0.65863(15) 0.36018(12) 0.24145(12) 0.0328(3) Uani 1 1 d .
C2 C 0.98679(17) 0.34538(14) 0.27068(15) 0.0433(4) Uani 1 1 d .
H2A H 0.9354 0.4236 0.2421 0.052 Uiso 1 1 calc R
C3 C 1.11977(18) 0.33083(16) 0.31425(16) 0.0499(4) Uani 1 1 d .
H3A H 1.1610 0.3992 0.3113 0.060 Uiso 1 1 calc R
C4 C 1.19217(17) 0.21681(17) 0.36193(15) 0.0494(4) Uani 1 1 d .
H4A H 1.2826 0.2064 0.3933 0.059 Uiso 1 1 calc R
C5 C 1.13380(17) 0.11789(15) 0.36422(14) 0.0448(4) Uani 1 1 d .
H5A H 1.1833 0.0393 0.3987 0.054 Uiso 1 1 calc R
C10 C 0.93398(17) -0.28221(13) 0.37313(13) 0.0401(3) Uani 1 1 d .
H10A H 1.0185 -0.2896 0.4112 0.048 Uiso 1 1 calc R
C11 C 0.88963(17) -0.38302(13) 0.36724(14) 0.0422(4) Uani 1 1 d .
H11A H 0.9446 -0.4592 0.4006 0.051 Uiso 1 1 calc R
C17 C 0.86894(18) 0.17257(15) -0.05857(14) 0.0459(4) Uani 1 1 d .
H17A H 0.9478 0.1729 -0.1165 0.055 Uiso 1 1 calc R
C16 C 0.88148(16) 0.22438(13) 0.02122(13) 0.0386(3) Uani 1 1 d .
C21 C 1.01886(18) 0.28377(18) 0.00540(16) 0.0540(4) Uani 1 1 d .
H21A H 1.0707 0.2946 -0.0729 0.081 Uiso 1 1 calc R
H21B H 1.0805 0.2322 0.0694 0.081 Uiso 1 1 calc R
H21C H 0.9943 0.3630 0.0095 0.081 Uiso 1 1 calc R
C23 C 0.51056(16) 0.16509(15) 0.20109(15) 0.0442(4) Uani 1 1 d .
H23A H 0.4343 0.1279 0.1849 0.066 Uiso 1 1 calc R
H23B H 0.4739 0.2466 0.1956 0.066 Uiso 1 1 calc R
H23C H 0.5400 0.1152 0.2820 0.066 Uiso 1 1 calc R
C29 C 0.59506(15) 0.32434(13) 0.36121(13) 0.0352(3) Uani 1 1 d .
C28 C 0.48419(15) 0.39860(13) 0.39085(13) 0.0377(3) Uani 1 1 d .
H28A H 0.4414 0.3724 0.4714 0.045 Uiso 1 1 calc R
C32 C 0.64303(19) 0.20424(14) 0.45890(14) 0.0492(4) Uani 1 1 d .
H32A H 0.5689 0.1832 0.5273 0.074 Uiso 1 1 calc R
H32B H 0.7344 0.2107 0.4852 0.074 Uiso 1 1 calc R
H32C H 0.6569 0.1410 0.4276 0.074 Uiso 1 1 calc R
B1 B 0.78147(17) 0.27562(14) 0.20553(14) 0.0331(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C22 0.0773(13) 0.0708(12) 0.0608(11) -0.0453(10) 0.0088(10) -0.0190(10)
C18 0.0562(10) 0.0394(8) 0.0399(8) -0.0211(7) -0.0003(7) -0.0063(7)
C19 0.0440(8) 0.0345(7) 0.0415(8) -0.0178(6) -0.0029(6) -0.0070(6)
C20 0.0356(7) 0.0295(7) 0.0355(7) -0.0133(6) -0.0018(6) -0.0018(6)
C15 0.0347(7) 0.0297(7) 0.0330(7) -0.0122(6) -0.0015(6) -0.0020(6)
C1 0.0338(7) 0.0345(7) 0.0367(7) -0.0197(6) 0.0009(6) -0.0035(6)
C6 0.0345(7) 0.0369(7) 0.0357(7) -0.0181(6) 0.0016(6) -0.0020(6)
C7 0.0385(8) 0.0343(7) 0.0396(8) -0.0143(6) -0.0001(6) 0.0003(6)
C8 0.0436(8) 0.0343(8) 0.0412(8) -0.0147(6) 0.0011(6) -0.0008(6)
C9 0.0429(8) 0.0319(7) 0.0362(8) -0.0142(6) 0.0049(6) -0.0052(6)
C14 0.0483(9) 0.0321(8) 0.0518(9) -0.0133(7) -0.0074(7) 0.0034(7)
C13 0.0454(9) 0.0436(9) 0.0518(10) -0.0180(8) -0.0089(7) -0.0027(7)
C12 0.0469(9) 0.0356(8) 0.0443(8) -0.0186(7) -0.0005(7) -0.0060(7)
C31 0.0436(9) 0.0469(9) 0.0641(11) -0.0286(8) -0.0049(8) 0.0059(7)
C27 0.0319(7) 0.0377(8) 0.0496(9) -0.0229(7) -0.0080(6) -0.0010(6)
C26 0.0387(8) 0.0310(7) 0.0452(8) -0.0154(6) -0.0140(6) -0.0013(6)
C25 0.0358(7) 0.0324(7) 0.0370(7) -0.0152(6) -0.0092(6) -0.0053(6)
C30 0.0491(9) 0.0392(8) 0.0386(8) -0.0112(7) -0.0064(7) -0.0067(7)
C24 0.0327(7) 0.0318(7) 0.0366(7) -0.0156(6) -0.0051(6) -0.0037(6)
C2 0.0423(8) 0.0411(8) 0.0557(10) -0.0290(8) -0.0017(7) -0.0052(7)
C3 0.0441(9) 0.0600(11) 0.0628(11) -0.0402(9) -0.0003(8) -0.0141(8)
C4 0.0332(8) 0.0733(12) 0.0532(10) -0.0369(9) -0.0035(7) -0.0048(8)
C5 0.0385(8) 0.0510(9) 0.0445(9) -0.0211(7) -0.0036(7) 0.0027(7)
C10 0.0410(8) 0.0371(8) 0.0415(8) -0.0164(7) -0.0038(6) 0.0000(6)
C11 0.0479(9) 0.0308(7) 0.0461(9) -0.0156(7) -0.0038(7) 0.0019(6)
C17 0.0486(9) 0.0503(9) 0.0399(8) -0.0226(7) 0.0082(7) -0.0064(7)
C16 0.0390(8) 0.0402(8) 0.0362(8) -0.0157(6) 0.0022(6) -0.0062(6)
C21 0.0451(9) 0.0730(12) 0.0487(10) -0.0294(9) 0.0130(7) -0.0221(8)
C23 0.0371(8) 0.0514(9) 0.0523(9) -0.0296(8) 0.0049(7) -0.0114(7)
C29 0.0371(7) 0.0330(7) 0.0362(7) -0.0147(6) -0.0043(6) -0.0020(6)
C28 0.0362(8) 0.0401(8) 0.0391(8) -0.0193(6) -0.0007(6) -0.0032(6)
C32 0.0574(10) 0.0420(9) 0.0382(8) -0.0112(7) 0.0011(7) 0.0053(7)
B1 0.0370(8) 0.0264(7) 0.0336(8) -0.0096(6) 0.0006(6) -0.0074(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 C22 H22A 109.5
C18 C22 H22B 109.5
H22A C22 H22B 109.5
C18 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C17 C18 C19 117.54(14)
C17 C18 C22 121.39(15)
C19 C18 C22 121.07(15)
C18 C19 C20 122.23(14)
C18 C19 H19A 118.9
C20 C19 H19A 118.9
C19 C20 C15 120.28(13)
C19 C20 C23 117.07(13)
C15 C20 C23 122.55(13)
C20 C15 C16 117.29(13)
C20 C15 B1 121.59(12)
C16 C15 B1 121.12(12)
C2 C1 C6 117.31(13)
C2 C1 B1 118.37(13)
C6 C1 B1 124.27(12)
C5 C6 C1 120.21(13)
C5 C6 C7 118.63(13)
C1 C6 C7 121.14(13)
C8 C7 C6 177.69(16)
C7 C8 C9 177.04(16)
C14 C9 C10 118.53(14)
C14 C9 C8 120.64(14)
C10 C9 C8 120.80(14)
C13 C14 C9 120.57(14)
C13 C14 H14A 119.7
C9 C14 H14A 119.7
C12 C13 C14 120.50(15)
C12 C13 H13A 119.8
C14 C13 H13A 119.8
C13 C12 C11 119.45(14)
C13 C12 H12A 120.3
C11 C12 H12A 120.3
C27 C31 H31A 109.5
C27 C31 H31B 109.5
H31A C31 H31B 109.5
C27 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C28 C27 C26 118.02(13)
C28 C27 C31 120.95(14)
C26 C27 C31 121.02(14)
C27 C26 C25 121.87(13)
C27 C26 H26A 119.1
C25 C26 H26A 119.1
C26 C25 C24 120.01(13)
C26 C25 C30 119.01(13)
C24 C25 C30 120.95(13)
C25 C30 H30A 109.5
C25 C30 H30B 109.5
H30A C30 H30B 109.5
C25 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
C25 C24 C29 118.08(13)
C25 C24 B1 121.02(12)
C29 C24 B1 120.89(12)
C3 C2 C1 121.99(15)
C3 C2 H2A 119.0
C1 C2 H2A 119.0
C4 C3 C2 119.74(15)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 120.20(15)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C4 C5 C6 120.46(15)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
C11 C10 C9 120.18(15)
C11 C10 H10A 119.9
C9 C10 H10A 119.9
C12 C11 C10 120.76(14)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C18 C17 C16 122.37(14)
C18 C17 H17A 118.8
C16 C17 H17A 118.8
C17 C16 C15 120.23(13)
C17 C16 C21 117.08(13)
C15 C16 C21 122.65(13)
C16 C21 H21A 109.5
C16 C21 H21B 109.5
H21A C21 H21B 109.5
C16 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C20 C23 H23A 109.5
C20 C23 H23B 109.5
H23A C23 H23B 109.5
C20 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C28 C29 C24 120.20(13)
C28 C29 C32 118.50(13)
C24 C29 C32 121.28(13)
C27 C28 C29 121.80(14)
C27 C28 H28A 119.1
C29 C28 H28A 119.1
C29 C32 H32A 109.5
C29 C32 H32B 109.5
H32A C32 H32B 109.5
C29 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
C1 B1 C15 120.67(12)
C1 B1 C24 116.09(12)
C15 B1 C24 123.20(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C22 C18 1.507(2)
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C18 C17 1.381(2)
C18 C19 1.386(2)
C19 C20 1.394(2)
C19 H19A 0.9500
C20 C15 1.413(2)
C20 C23 1.511(2)
C15 C16 1.4193(19)
C15 B1 1.574(2)
C1 C2 1.399(2)
C1 C6 1.4119(19)
C1 B1 1.571(2)
C6 C5 1.400(2)
C6 C7 1.436(2)
C7 C8 1.196(2)
C8 C9 1.433(2)
C9 C14 1.395(2)
C9 C10 1.396(2)
C14 C13 1.380(2)
C14 H14A 0.9500
C13 C12 1.378(2)
C13 H13A 0.9500
C12 C11 1.380(2)
C12 H12A 0.9500
C31 C27 1.508(2)
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
C27 C28 1.387(2)
C27 C26 1.389(2)
C26 C25 1.395(2)
C26 H26A 0.9500
C25 C24 1.4087(19)
C25 C30 1.512(2)
C30 H30A 0.9800
C30 H30B 0.9800
C30 H30C 0.9800
C24 C29 1.4147(19)
C24 B1 1.574(2)
C2 C3 1.384(2)
C2 H2A 0.9500
C3 C4 1.378(2)
C3 H3A 0.9500
C4 C5 1.379(2)
C4 H4A 0.9500
C5 H5A 0.9500
C10 C11 1.381(2)
C10 H10A 0.9500
C11 H11A 0.9500
C17 C16 1.392(2)
C17 H17A 0.9500
C16 C21 1.514(2)
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C29 C28 1.390(2)
C29 C32 1.512(2)
C28 H28A 0.9500
C32 H32A 0.9800
C32 H32B 0.9800
C32 H32C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C17 C18 C19 C20 -1.6(2)
C22 C18 C19 C20 178.18(15)
C18 C19 C20 C15 -0.1(2)
C18 C19 C20 C23 -176.68(14)
C19 C20 C15 C16 2.1(2)
C23 C20 C15 C16 178.50(13)
C19 C20 C15 B1 -177.01(13)
C23 C20 C15 B1 -0.6(2)
C2 C1 C6 C5 -0.4(2)
B1 C1 C6 C5 176.78(13)
C2 C1 C6 C7 178.30(13)
B1 C1 C6 C7 -4.5(2)
C5 C6 C7 C8 -5(4)
C1 C6 C7 C8 177(100)
C6 C7 C8 C9 -94(5)
C7 C8 C9 C14 -78(3)
C7 C8 C9 C10 100(3)
C10 C9 C14 C13 -0.5(2)
C8 C9 C14 C13 177.55(15)
C9 C14 C13 C12 0.2(2)
C14 C13 C12 C11 -0.1(2)
C28 C27 C26 C25 0.6(2)
C31 C27 C26 C25 179.28(13)
C27 C26 C25 C24 0.1(2)
C27 C26 C25 C30 -177.64(13)
C26 C25 C24 C29 -1.36(19)
C30 C25 C24 C29 176.32(13)
C26 C25 C24 B1 178.94(13)
C30 C25 C24 B1 -3.39(19)
C6 C1 C2 C3 3.0(2)
B1 C1 C2 C3 -174.39(14)
C1 C2 C3 C4 -3.4(2)
C2 C3 C4 C5 1.2(2)
C3 C4 C5 C6 1.3(2)
C1 C6 C5 C4 -1.7(2)
C7 C6 C5 C4 179.58(14)
C14 C9 C10 C11 0.8(2)
C8 C9 C10 C11 -177.31(14)
C13 C12 C11 C10 0.3(2)
C9 C10 C11 C12 -0.7(2)
C19 C18 C17 C16 1.2(2)
C22 C18 C17 C16 -178.57(16)
C18 C17 C16 C15 0.8(2)
C18 C17 C16 C21 -176.99(15)
C20 C15 C16 C17 -2.4(2)
B1 C15 C16 C17 176.65(14)
C20 C15 C16 C21 175.25(14)
B1 C15 C16 C21 -5.7(2)
C25 C24 C29 C28 1.9(2)
B1 C24 C29 C28 -178.35(13)
C25 C24 C29 C32 -179.41(13)
B1 C24 C29 C32 0.3(2)
C26 C27 C28 C29 0.0(2)
C31 C27 C28 C29 -178.68(14)
C24 C29 C28 C27 -1.3(2)
C32 C29 C28 C27 -179.96(14)
C2 C1 B1 C15 130.82(14)
C6 C1 B1 C15 -46.31(19)
C2 C1 B1 C24 -46.97(18)
C6 C1 B1 C24 135.89(14)
C20 C15 B1 C1 137.32(14)
C16 C15 B1 C1 -41.74(19)
C20 C15 B1 C24 -45.05(19)
C16 C15 B1 C24 135.90(14)
C25 C24 B1 C1 116.77(14)
C29 C24 B1 C1 -62.92(17)
C25 C24 B1 C15 -60.96(18)
C29 C24 B1 C15 119.34(15)
|
1502033.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502033.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502033
loop_
_publ_author_name
'Sun, Christina'
'Lu, Jiasheng'
'Wang, Suning'
_publ_section_title
;
Donor-acceptor assisted alkyne hydration: a luminescent boron-stabilized
enol.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1226
_journal_page_last 1229
_journal_paper_doi 10.1021/ol200106a
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C31 H30 B N'
_chemical_formula_weight 427.37
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 92.161(16)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.148(12)
_cell_length_b 23.74(3)
_cell_length_c 12.404(18)
_cell_measurement_reflns_used 1168
_cell_measurement_temperature 180(2)
_cell_measurement_theta_max 20.61
_cell_measurement_theta_min 2.38
_cell_volume 2398(6)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 180(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.1592
_diffrn_reflns_av_sigmaI/netI 0.1720
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 29
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 16510
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 2.38
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.067
_exptl_absorpt_correction_T_max 0.9987
_exptl_absorpt_correction_T_min 0.9933
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.184
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 912
_exptl_crystal_size_max 0.10
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.411
_refine_diff_density_min -0.386
_refine_diff_density_rms 0.094
_refine_ls_extinction_coef 0.026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.097
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 305
_refine_ls_number_reflns 4640
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.097
_refine_ls_R_factor_all 0.2376
_refine_ls_R_factor_gt 0.1279
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1628P)^2^+1.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.3261
_refine_ls_wR_factor_ref 0.3848
_reflns_number_gt 1951
_reflns_number_total 4640
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200106a_si_003.cif
_cod_data_source_block louis21
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502033
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.9753(8) 0.2432(3) 0.6050(5) 0.0629(17) Uani 1 1 d .
B1 B 0.8205(9) 0.4654(3) 0.7665(6) 0.047(2) Uani 1 1 d .
C1 C 0.7195(8) 0.4286(3) 0.8478(5) 0.0462(17) Uani 1 1 d .
C2 C 0.6627(8) 0.4537(3) 0.9400(6) 0.0535(19) Uani 1 1 d .
H2A H 0.6745 0.4933 0.9480 0.064 Uiso 1 1 calc R
C3 C 0.5904(9) 0.4243(3) 1.0201(6) 0.059(2) Uani 1 1 d .
H3A H 0.5571 0.4431 1.0833 0.071 Uiso 1 1 calc R
C4 C 0.5662(9) 0.3669(4) 1.0084(6) 0.061(2) Uani 1 1 d .
H4A H 0.5149 0.3460 1.0631 0.073 Uiso 1 1 calc R
C5 C 0.6172(8) 0.3403(3) 0.9166(6) 0.0531(18) Uani 1 1 d .
H5A H 0.5969 0.3012 0.9074 0.064 Uiso 1 1 calc R
C6 C 0.6976(8) 0.3696(3) 0.8374(5) 0.0457(17) Uani 1 1 d .
C7 C 0.7514(9) 0.3392(3) 0.7457(6) 0.0530(18) Uani 1 1 d .
C8 C 0.7962(9) 0.3122(3) 0.6726(6) 0.0515(18) Uani 1 1 d .
C9 C 0.8661(9) 0.2839(3) 0.5813(6) 0.0539(19) Uani 1 1 d .
C10 C 0.8244(9) 0.3009(3) 0.4788(6) 0.057(2) Uani 1 1 d .
H10A H 0.7435 0.3292 0.4666 0.069 Uiso 1 1 calc R
C11 C 0.8995(10) 0.2770(3) 0.3945(6) 0.064(2) Uani 1 1 d .
H11A H 0.8744 0.2890 0.3227 0.077 Uiso 1 1 calc R
C12 C 1.0141(10) 0.2346(3) 0.4154(7) 0.069(2) Uani 1 1 d .
H12A H 1.0673 0.2158 0.3587 0.083 Uiso 1 1 calc R
C13 C 1.0466(10) 0.2212(4) 0.5206(6) 0.068(2) Uani 1 1 d .
H13A H 1.1284 0.1933 0.5349 0.082 Uiso 1 1 calc R
C14 C 0.7644(8) 0.5277(3) 0.7466(5) 0.0477(17) Uani 1 1 d .
C15 C 0.8677(8) 0.5740(3) 0.7657(5) 0.0494(18) Uani 1 1 d .
C16 C 0.8098(9) 0.6283(3) 0.7564(5) 0.0553(19) Uani 1 1 d .
H16A H 0.8844 0.6584 0.7708 0.066 Uiso 1 1 calc R
C17 C 0.6474(9) 0.6415(3) 0.7271(6) 0.0557(19) Uani 1 1 d .
C18 C 0.5464(9) 0.5954(3) 0.7035(6) 0.0546(19) Uani 1 1 d .
H18A H 0.4362 0.6025 0.6796 0.066 Uiso 1 1 calc R
C19 C 0.5968(9) 0.5406(3) 0.7127(5) 0.0500(18) Uani 1 1 d .
C20 C 0.4760(9) 0.4944(3) 0.6854(6) 0.066(2) Uani 1 1 d .
H20A H 0.3976 0.5075 0.6290 0.099 Uiso 1 1 calc R
H20B H 0.4168 0.4843 0.7499 0.099 Uiso 1 1 calc R
H20C H 0.5349 0.4614 0.6595 0.099 Uiso 1 1 calc R
C21 C 0.5900(10) 0.7001(3) 0.7195(6) 0.069(2) Uani 1 1 d .
H21A H 0.4839 0.7034 0.7536 0.104 Uiso 1 1 calc R
H21B H 0.5777 0.7110 0.6434 0.104 Uiso 1 1 calc R
H21C H 0.6702 0.7248 0.7565 0.104 Uiso 1 1 calc R
C22 C 1.0471(9) 0.5668(3) 0.8004(6) 0.061(2) Uani 1 1 d .
H22A H 1.1026 0.6034 0.7985 0.092 Uiso 1 1 calc R
H22B H 1.0996 0.5407 0.7512 0.092 Uiso 1 1 calc R
H22C H 1.0550 0.5517 0.8739 0.092 Uiso 1 1 calc R
C23 C 0.9726(8) 0.4376(3) 0.7177(5) 0.0460(17) Uani 1 1 d .
C24 C 1.1017(8) 0.4135(3) 0.7833(5) 0.0470(17) Uani 1 1 d .
C25 C 1.2238(8) 0.3839(3) 0.7344(6) 0.0485(17) Uani 1 1 d .
H25A H 1.3091 0.3680 0.7788 0.058 Uiso 1 1 calc R
C28 C 0.9813(8) 0.4313(3) 0.6051(5) 0.0487(17) Uani 1 1 d .
C26 C 1.2290(8) 0.3764(3) 0.6261(6) 0.0522(18) Uani 1 1 d .
C27 C 1.1060(9) 0.4008(3) 0.5633(6) 0.0535(18) Uani 1 1 d .
H27A H 1.1078 0.3963 0.4873 0.064 Uiso 1 1 calc R
C31 C 0.8434(9) 0.4531(3) 0.5281(6) 0.0550(19) Uani 1 1 d .
H31A H 0.8772 0.4495 0.4534 0.082 Uiso 1 1 calc R
H31B H 0.8214 0.4928 0.5440 0.082 Uiso 1 1 calc R
H31C H 0.7436 0.4309 0.5378 0.082 Uiso 1 1 calc R
C30 C 1.3628(10) 0.3428(3) 0.5754(7) 0.071(2) Uani 1 1 d .
H30A H 1.4298 0.3241 0.6320 0.107 Uiso 1 1 calc R
H30B H 1.4322 0.3681 0.5344 0.107 Uiso 1 1 calc R
H30C H 1.3135 0.3145 0.5268 0.107 Uiso 1 1 calc R
C29 C 1.1057(9) 0.4198(3) 0.9038(5) 0.058(2) Uani 1 1 d .
H29A H 1.2138 0.4085 0.9336 0.087 Uiso 1 1 calc R
H29B H 1.0209 0.3959 0.9340 0.087 Uiso 1 1 calc R
H29C H 1.0851 0.4592 0.9225 0.087 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.064(4) 0.064(4) 0.059(4) -0.007(3) -0.010(3) 0.006(3)
B1 0.034(5) 0.062(5) 0.044(4) -0.004(4) -0.014(3) -0.004(4)
C1 0.034(4) 0.061(5) 0.043(4) -0.001(3) -0.006(3) 0.004(3)
C2 0.045(4) 0.063(4) 0.052(4) 0.002(4) -0.013(3) 0.007(3)
C3 0.057(5) 0.072(5) 0.047(4) -0.006(4) -0.006(4) 0.019(4)
C4 0.052(5) 0.086(6) 0.044(4) 0.019(4) 0.005(4) 0.013(4)
C5 0.041(4) 0.055(4) 0.063(5) 0.009(4) -0.002(4) -0.001(3)
C6 0.039(4) 0.058(4) 0.040(4) 0.003(3) -0.010(3) 0.002(3)
C7 0.045(4) 0.062(5) 0.051(5) 0.006(4) -0.010(4) -0.002(3)
C8 0.046(4) 0.065(5) 0.043(4) -0.001(4) -0.003(3) -0.003(4)
C9 0.060(5) 0.050(4) 0.052(4) -0.004(3) -0.008(4) 0.001(4)
C10 0.061(5) 0.061(5) 0.049(5) -0.010(4) -0.005(4) -0.002(4)
C11 0.071(6) 0.071(5) 0.050(5) 0.003(4) -0.005(4) -0.016(4)
C12 0.063(6) 0.073(5) 0.071(6) -0.015(4) 0.010(4) -0.007(4)
C13 0.068(6) 0.086(6) 0.050(5) -0.009(4) -0.007(4) 0.014(4)
C14 0.039(4) 0.052(4) 0.051(4) 0.005(3) -0.005(3) -0.003(3)
C15 0.045(4) 0.060(5) 0.042(4) -0.001(3) -0.010(3) -0.003(3)
C16 0.058(5) 0.051(4) 0.056(4) -0.001(3) -0.006(4) -0.003(4)
C17 0.053(5) 0.057(5) 0.057(4) 0.004(3) -0.002(4) 0.004(4)
C18 0.047(4) 0.063(5) 0.053(4) 0.000(3) -0.007(3) 0.008(4)
C19 0.046(4) 0.048(4) 0.055(4) 0.004(3) -0.010(3) -0.004(3)
C20 0.050(5) 0.078(5) 0.068(5) -0.003(4) -0.015(4) 0.000(4)
C21 0.072(6) 0.065(5) 0.070(5) 0.005(4) 0.005(4) 0.007(4)
C22 0.047(5) 0.056(4) 0.079(5) 0.004(4) -0.014(4) -0.007(3)
C23 0.041(4) 0.051(4) 0.044(4) -0.002(3) -0.012(3) -0.004(3)
C24 0.034(4) 0.052(4) 0.054(4) -0.003(3) -0.006(3) -0.003(3)
C25 0.036(4) 0.054(4) 0.056(5) 0.008(3) -0.006(3) -0.005(3)
C28 0.037(4) 0.067(4) 0.041(4) 0.008(3) -0.004(3) -0.004(3)
C26 0.040(4) 0.061(4) 0.056(5) -0.001(3) 0.006(3) 0.003(3)
C27 0.042(4) 0.068(5) 0.050(4) -0.004(4) -0.005(3) -0.004(4)
C31 0.044(4) 0.063(4) 0.056(4) 0.004(3) -0.008(3) 0.008(3)
C30 0.052(5) 0.079(5) 0.083(6) -0.001(5) -0.002(4) 0.009(4)
C29 0.051(5) 0.074(5) 0.049(4) -0.001(4) -0.008(3) 0.010(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 N1 C9 114.8(6)
C23 B1 C14 125.1(6)
C23 B1 C1 117.1(6)
C14 B1 C1 117.7(6)
C2 C1 C6 117.1(6)
C2 C1 B1 119.0(6)
C6 C1 B1 123.6(6)
C3 C2 C1 123.2(7)
C3 C2 H2A 118.4
C1 C2 H2A 118.4
C2 C3 C4 119.4(7)
C2 C3 H3A 120.3
C4 C3 H3A 120.3
C5 C4 C3 119.4(7)
C5 C4 H4A 120.3
C3 C4 H4A 120.3
C4 C5 C6 121.3(7)
C4 C5 H5A 119.3
C6 C5 H5A 119.3
C5 C6 C1 119.5(6)
C5 C6 C7 118.4(6)
C1 C6 C7 122.1(6)
C8 C7 C6 177.5(7)
C7 C8 C9 173.4(8)
N1 C9 C10 123.9(7)
N1 C9 C8 116.1(6)
C10 C9 C8 120.0(7)
C11 C10 C9 119.4(7)
C11 C10 H10A 120.3
C9 C10 H10A 120.3
C10 C11 C12 118.6(7)
C10 C11 H11A 120.7
C12 C11 H11A 120.7
C13 C12 C11 117.0(7)
C13 C12 H12A 121.5
C11 C12 H12A 121.5
N1 C13 C12 126.2(8)
N1 C13 H13A 116.9
C12 C13 H13A 116.9
C15 C14 C19 115.9(6)
C15 C14 B1 123.1(6)
C19 C14 B1 120.9(6)
C16 C15 C14 121.3(6)
C16 C15 C22 116.9(6)
C14 C15 C22 121.7(6)
C15 C16 C17 123.4(7)
C15 C16 H16A 118.3
C17 C16 H16A 118.3
C18 C17 C16 115.2(7)
C18 C17 C21 123.1(7)
C16 C17 C21 121.7(7)
C19 C18 C17 123.8(7)
C19 C18 H18A 118.1
C17 C18 H18A 118.1
C18 C19 C14 120.2(6)
C18 C19 C20 118.9(6)
C14 C19 C20 120.9(6)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C17 C21 H21A 109.5
C17 C21 H21B 109.5
H21A C21 H21B 109.5
C17 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C15 C22 H22A 109.5
C15 C22 H22B 109.5
H22A C22 H22B 109.5
C15 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C28 C23 C24 117.3(6)
C28 C23 B1 120.2(6)
C24 C23 B1 122.2(6)
C25 C24 C23 118.9(6)
C25 C24 C29 120.0(6)
C23 C24 C29 121.1(6)
C26 C25 C24 123.6(6)
C26 C25 H25A 118.2
C24 C25 H25A 118.2
C27 C28 C23 119.9(6)
C27 C28 C31 118.7(6)
C23 C28 C31 121.1(6)
C25 C26 C27 117.1(7)
C25 C26 C30 122.2(7)
C27 C26 C30 120.7(7)
C28 C27 C26 123.2(7)
C28 C27 H27A 118.4
C26 C27 H27A 118.4
C28 C31 H31A 109.5
C28 C31 H31B 109.5
H31A C31 H31B 109.5
C28 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C26 C30 H30A 109.5
C26 C30 H30B 109.5
H30A C30 H30B 109.5
C26 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
C24 C29 H29A 109.5
C24 C29 H29B 109.5
H29A C29 H29B 109.5
C24 C29 H29C 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.324(9)
N1 C9 1.340(9)
B1 C23 1.547(10)
B1 C14 1.563(11)
B1 C1 1.588(11)
C1 C2 1.386(9)
C1 C6 1.416(10)
C2 C3 1.366(10)
C2 H2A 0.9500
C3 C4 1.384(11)
C3 H3A 0.9500
C4 C5 1.380(10)
C4 H4A 0.9500
C5 C6 1.388(9)
C5 H5A 0.9500
C6 C7 1.430(10)
C7 C8 1.178(9)
C8 C9 1.452(10)
C9 C10 1.364(10)
C10 C11 1.355(10)
C10 H10A 0.9500
C11 C12 1.391(11)
C11 H11A 0.9500
C12 C13 1.359(11)
C12 H12A 0.9500
C13 H13A 0.9500
C14 C15 1.400(9)
C14 C19 1.447(9)
C15 C16 1.377(10)
C15 C22 1.518(10)
C16 C17 1.395(10)
C16 H16A 0.9500
C17 C18 1.394(10)
C17 C21 1.468(10)
C18 C19 1.368(9)
C18 H18A 0.9500
C19 C20 1.503(10)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 C28 1.410(9)
C23 C24 1.425(9)
C24 C25 1.378(9)
C24 C29 1.501(9)
C25 C26 1.358(9)
C25 H25A 0.9500
C28 C27 1.366(9)
C28 C31 1.536(9)
C26 C27 1.374(10)
C26 C30 1.506(10)
C27 H27A 0.9500
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
C30 H30A 0.9800
C30 H30B 0.9800
C30 H30C 0.9800
C29 H29A 0.9800
C29 H29B 0.9800
C29 H29C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C23 B1 C1 C2 138.5(6)
C14 B1 C1 C2 -38.3(8)
C23 B1 C1 C6 -34.9(8)
C14 B1 C1 C6 148.3(6)
C6 C1 C2 C3 1.1(10)
B1 C1 C2 C3 -172.8(6)
C1 C2 C3 C4 -2.5(11)
C2 C3 C4 C5 0.8(10)
C3 C4 C5 C6 2.3(10)
C4 C5 C6 C1 -3.7(10)
C4 C5 C6 C7 178.2(6)
C2 C1 C6 C5 2.0(9)
B1 C1 C6 C5 175.5(6)
C2 C1 C6 C7 -180.0(6)
B1 C1 C6 C7 -6.4(9)
C5 C6 C7 C8 -28(17)
C1 C6 C7 C8 154(17)
C6 C7 C8 C9 -126(16)
C13 N1 C9 C10 2.5(11)
C13 N1 C9 C8 -174.9(7)
C7 C8 C9 N1 95(7)
C7 C8 C9 C10 -83(7)
N1 C9 C10 C11 -2.1(11)
C8 C9 C10 C11 175.2(7)
C9 C10 C11 C12 1.8(11)
C10 C11 C12 C13 -2.0(11)
C9 N1 C13 C12 -2.8(12)
C11 C12 C13 N1 2.6(13)
C23 B1 C14 C15 -54.5(9)
C1 B1 C14 C15 122.1(7)
C23 B1 C14 C19 129.1(7)
C1 B1 C14 C19 -54.3(8)
C19 C14 C15 C16 2.4(10)
B1 C14 C15 C16 -174.2(6)
C19 C14 C15 C22 -179.2(6)
B1 C14 C15 C22 4.2(10)
C14 C15 C16 C17 -0.5(11)
C22 C15 C16 C17 -179.0(7)
C15 C16 C17 C18 -2.2(10)
C15 C16 C17 C21 179.1(7)
C16 C17 C18 C19 3.1(11)
C21 C17 C18 C19 -178.3(7)
C17 C18 C19 C14 -1.3(11)
C17 C18 C19 C20 179.7(7)
C15 C14 C19 C18 -1.5(10)
B1 C14 C19 C18 175.1(6)
C15 C14 C19 C20 177.5(6)
B1 C14 C19 C20 -5.9(10)
C14 B1 C23 C28 -63.1(9)
C1 B1 C23 C28 120.3(7)
C14 B1 C23 C24 122.1(7)
C1 B1 C23 C24 -54.5(8)
C28 C23 C24 C25 -2.2(9)
B1 C23 C24 C25 172.7(6)
C28 C23 C24 C29 177.9(6)
B1 C23 C24 C29 -7.2(9)
C23 C24 C25 C26 0.1(10)
C29 C24 C25 C26 -180.0(7)
C24 C23 C28 C27 3.0(10)
B1 C23 C28 C27 -172.1(6)
C24 C23 C28 C31 176.7(6)
B1 C23 C28 C31 1.6(10)
C24 C25 C26 C27 1.2(10)
C24 C25 C26 C30 -178.8(7)
C23 C28 C27 C26 -1.7(11)
C31 C28 C27 C26 -175.5(7)
C25 C26 C27 C28 -0.5(10)
C30 C26 C27 C28 179.6(7)
|
1502034.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502034
loop_
_publ_author_name
'Sun, Christina'
'Lu, Jiasheng'
'Wang, Suning'
_publ_section_title
;
Donor-acceptor assisted alkyne hydration: a luminescent boron-stabilized
enol.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1226
_journal_page_last 1229
_journal_paper_doi 10.1021/ol200106a
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C31 H32 B N O'
_chemical_formula_weight 445.39
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 98.526(13)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 13.196(15)
_cell_length_b 13.291(15)
_cell_length_c 15.960(18)
_cell_measurement_reflns_used 809
_cell_measurement_temperature 180(2)
_cell_measurement_theta_max 17.66
_cell_measurement_theta_min 2.19
_cell_volume 2768(5)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 180(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.1889
_diffrn_reflns_av_sigmaI/netI 0.1909
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 25307
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 2.19
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.063
_exptl_absorpt_correction_T_max 0.9969
_exptl_absorpt_correction_T_min 0.9969
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.069
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 952
_exptl_crystal_size_max 0.05
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.05
_platon_squeeze_details
'A disordered diethylether solvent molecule was removed by SQUEEZE.'
_refine_diff_density_max 0.278
_refine_diff_density_min -0.385
_refine_diff_density_rms 0.078
_refine_ls_extinction_coef 0.0035(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 0.915
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 317
_refine_ls_number_reflns 5443
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 0.915
_refine_ls_R_factor_all 0.2209
_refine_ls_R_factor_gt 0.0982
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2132
_refine_ls_wR_factor_ref 0.2674
_reflns_number_gt 1952
_reflns_number_total 5443
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200106a_si_004.cif
_cod_data_source_block louis20
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502034
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.4496(3) 0.1304(3) -0.4798(2) 0.0435(10) Uani 1 1 d D
H1A H 0.387(3) 0.134(3) -0.453(3) 0.052 Uiso 1 1 d D
B1 B 0.3209(4) 0.1291(4) -0.2557(3) 0.0391(13) Uani 1 1 d .
O1 O 0.3932(3) 0.1348(2) -0.32838(17) 0.0428(8) Uani 1 1 d .
C1 C 0.4132(4) 0.1241(3) -0.1769(3) 0.0404(12) Uani 1 1 d .
C2 C 0.4166(4) 0.1271(3) -0.0871(3) 0.0472(13) Uani 1 1 d .
H2A H 0.3545 0.1299 -0.0638 0.057 Uiso 1 1 calc R
C3 C 0.5090(4) 0.1259(3) -0.0338(3) 0.0473(13) Uani 1 1 d .
H3A H 0.5092 0.1223 0.0257 0.057 Uiso 1 1 calc R
C4 C 0.6015(4) 0.1300(3) -0.0649(3) 0.0500(13) Uani 1 1 d .
H4A H 0.6644 0.1318 -0.0272 0.060 Uiso 1 1 calc R
C5 C 0.6010(4) 0.1315(3) -0.1523(3) 0.0419(12) Uani 1 1 d .
H5A H 0.6635 0.1332 -0.1752 0.050 Uiso 1 1 calc R
C6 C 0.5088(4) 0.1304(3) -0.2046(3) 0.0386(11) Uani 1 1 d .
C7 C 0.4919(4) 0.1324(3) -0.2989(3) 0.0398(12) Uani 1 1 d .
C8 C 0.5663(4) 0.1316(3) -0.3487(3) 0.0410(12) Uani 1 1 d .
H8A H 0.6356 0.1339 -0.3221 0.049 Uiso 1 1 calc R
C9 C 0.5466(4) 0.1273(3) -0.4397(3) 0.0420(12) Uani 1 1 d .
C10 C 0.6247(4) 0.1205(3) -0.4900(3) 0.0473(13) Uani 1 1 d .
H10A H 0.6944 0.1199 -0.4644 0.057 Uiso 1 1 calc R
C11 C 0.6000(4) 0.1148(3) -0.5774(3) 0.0468(13) Uani 1 1 d .
H11A H 0.6529 0.1077 -0.6114 0.056 Uiso 1 1 calc R
C12 C 0.5001(4) 0.1191(3) -0.6146(3) 0.0459(13) Uani 1 1 d .
H12A H 0.4840 0.1164 -0.6746 0.055 Uiso 1 1 calc R
C13 C 0.4232(4) 0.1272(3) -0.5668(3) 0.0488(13) Uani 1 1 d .
H13A H 0.3535 0.1305 -0.5924 0.059 Uiso 1 1 calc R
C14 C 0.2637(4) 0.2367(4) -0.2470(3) 0.0415(12) Uani 1 1 d .
C15 C 0.2875(4) 0.3315(4) -0.2794(3) 0.0438(12) Uani 1 1 d .
C16 C 0.2423(4) 0.4183(4) -0.2570(3) 0.0470(13) Uani 1 1 d .
H16A H 0.2614 0.4801 -0.2802 0.056 Uiso 1 1 calc R
C17 C 0.1696(4) 0.4204(4) -0.2018(3) 0.0482(13) Uani 1 1 d .
C18 C 0.1451(4) 0.3287(4) -0.1713(3) 0.0505(14) Uani 1 1 d .
H18A H 0.0951 0.3270 -0.1342 0.061 Uiso 1 1 calc R
C19 C 0.1876(4) 0.2401(4) -0.1904(3) 0.0456(13) Uani 1 1 d .
C20 C 0.1498(4) 0.1451(4) -0.1546(3) 0.0572(15) Uani 1 1 d .
H20A H 0.1251 0.1601 -0.1010 0.086 Uiso 1 1 calc R
H20B H 0.2060 0.0963 -0.1445 0.086 Uiso 1 1 calc R
H20C H 0.0938 0.1169 -0.1949 0.086 Uiso 1 1 calc R
C21 C 0.3645(4) 0.3447(4) -0.3421(3) 0.0547(15) Uani 1 1 d .
H21A H 0.3762 0.4166 -0.3505 0.082 Uiso 1 1 calc R
H21B H 0.3369 0.3137 -0.3964 0.082 Uiso 1 1 calc R
H21C H 0.4294 0.3123 -0.3193 0.082 Uiso 1 1 calc R
C22 C 0.1204(4) 0.5192(4) -0.1799(4) 0.0680(17) Uani 1 1 d .
H22A H 0.1365 0.5314 -0.1188 0.102 Uiso 1 1 calc R
H22B H 0.0459 0.5149 -0.1961 0.102 Uiso 1 1 calc R
H22C H 0.1472 0.5745 -0.2108 0.102 Uiso 1 1 calc R
C23 C 0.2527(4) 0.0311(4) -0.2875(3) 0.0431(13) Uani 1 1 d .
C24 C 0.2597(4) -0.0655(4) -0.2502(3) 0.0500(14) Uani 1 1 d .
C25 C 0.2104(4) -0.1490(4) -0.2887(3) 0.0528(14) Uani 1 1 d .
H25A H 0.2186 -0.2125 -0.2611 0.063 Uiso 1 1 calc R
C26 C 0.1492(4) -0.1416(4) -0.3670(3) 0.0513(14) Uani 1 1 d .
C27 C 0.1373(4) -0.0493(4) -0.4019(3) 0.0535(14) Uani 1 1 d .
H27A H 0.0932 -0.0429 -0.4544 0.064 Uiso 1 1 calc R
C28 C 0.1848(4) 0.0367(4) -0.3668(3) 0.0500(14) Uani 1 1 d .
C29 C 0.1645(4) 0.1354(4) -0.4141(3) 0.0617(15) Uani 1 1 d .
H29A H 0.1291 0.1222 -0.4714 0.092 Uiso 1 1 calc R
H29B H 0.2298 0.1693 -0.4175 0.092 Uiso 1 1 calc R
H29C H 0.1217 0.1785 -0.3840 0.092 Uiso 1 1 calc R
C30 C 0.3296(4) -0.0875(4) -0.1655(3) 0.0629(16) Uani 1 1 d .
H30A H 0.3288 -0.1598 -0.1536 0.094 Uiso 1 1 calc R
H30B H 0.3045 -0.0504 -0.1197 0.094 Uiso 1 1 calc R
H30C H 0.3998 -0.0663 -0.1697 0.094 Uiso 1 1 calc R
C31 C 0.1046(4) -0.2362(4) -0.4102(4) 0.0772(19) Uani 1 1 d .
H31A H 0.0425 -0.2193 -0.4493 0.116 Uiso 1 1 calc R
H31B H 0.0874 -0.2837 -0.3675 0.116 Uiso 1 1 calc R
H31C H 0.1549 -0.2669 -0.4417 0.116 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.057(3) 0.049(3) 0.025(2) 0.0001(19) 0.010(2) 0.000(2)
B1 0.055(4) 0.047(3) 0.017(2) 0.009(2) 0.010(2) 0.003(3)
O1 0.055(2) 0.059(2) 0.0166(16) -0.0002(14) 0.0116(15) 0.0021(17)
C1 0.062(3) 0.033(3) 0.027(2) -0.003(2) 0.009(2) 0.002(2)
C2 0.075(4) 0.048(3) 0.021(2) 0.002(2) 0.016(3) 0.009(3)
C3 0.072(4) 0.047(3) 0.022(3) 0.004(2) 0.004(3) -0.003(3)
C4 0.071(4) 0.049(3) 0.026(3) 0.001(2) -0.004(3) -0.003(3)
C5 0.057(3) 0.045(3) 0.024(2) 0.000(2) 0.007(2) 0.005(2)
C6 0.053(3) 0.037(3) 0.026(2) 0.003(2) 0.007(2) 0.004(2)
C7 0.056(3) 0.042(3) 0.024(2) -0.003(2) 0.012(2) 0.000(3)
C8 0.054(3) 0.044(3) 0.025(2) -0.002(2) 0.007(2) -0.004(2)
C9 0.052(3) 0.041(3) 0.035(3) 0.002(2) 0.009(2) -0.003(2)
C10 0.052(3) 0.059(3) 0.033(3) 0.005(2) 0.010(2) 0.004(3)
C11 0.060(4) 0.055(3) 0.030(3) 0.000(2) 0.021(3) 0.002(3)
C12 0.071(4) 0.048(3) 0.019(2) -0.007(2) 0.009(3) -0.002(3)
C13 0.065(4) 0.054(3) 0.026(3) 0.009(2) 0.002(2) -0.005(3)
C14 0.050(3) 0.055(3) 0.018(2) 0.000(2) 0.001(2) -0.008(2)
C15 0.058(3) 0.047(3) 0.025(3) 0.003(2) 0.003(2) -0.008(3)
C16 0.065(4) 0.041(3) 0.033(3) 0.004(2) 0.002(3) 0.006(3)
C17 0.057(3) 0.058(4) 0.031(3) -0.006(3) 0.008(2) 0.007(3)
C18 0.063(4) 0.060(4) 0.030(3) 0.006(3) 0.015(2) 0.002(3)
C19 0.063(3) 0.045(3) 0.030(3) 0.006(2) 0.009(2) 0.005(3)
C20 0.071(4) 0.065(4) 0.041(3) 0.000(3) 0.024(3) 0.001(3)
C21 0.084(4) 0.045(3) 0.041(3) 0.001(2) 0.028(3) 0.001(3)
C22 0.077(4) 0.078(4) 0.051(4) -0.003(3) 0.016(3) 0.014(3)
C23 0.056(3) 0.053(3) 0.021(3) -0.001(2) 0.011(2) 0.003(3)
C24 0.070(4) 0.051(3) 0.034(3) -0.006(3) 0.023(3) -0.004(3)
C25 0.063(4) 0.054(4) 0.045(3) -0.008(3) 0.019(3) -0.002(3)
C26 0.062(4) 0.051(4) 0.043(3) -0.016(3) 0.016(3) -0.011(3)
C27 0.055(4) 0.065(4) 0.041(3) -0.009(3) 0.008(3) -0.002(3)
C28 0.055(3) 0.060(4) 0.035(3) -0.004(3) 0.006(3) -0.001(3)
C29 0.073(4) 0.074(4) 0.034(3) 0.002(3) -0.006(3) 0.001(3)
C30 0.109(5) 0.056(3) 0.023(3) 0.008(2) 0.009(3) 0.006(3)
C31 0.070(4) 0.088(5) 0.074(5) -0.018(4) 0.014(3) -0.009(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C13 123.9(4)
C9 N1 H1A 127(3)
C13 N1 H1A 109(3)
O1 B1 C1 96.0(4)
O1 B1 C23 99.9(3)
C1 B1 C23 122.0(4)
O1 B1 C14 110.5(4)
C1 B1 C14 105.9(4)
C23 B1 C14 119.3(4)
C7 O1 B1 113.7(3)
C6 C1 C2 114.8(4)
C6 C1 B1 111.2(4)
C2 C1 B1 133.5(4)
C3 C2 C1 120.8(5)
C3 C2 H2A 119.6
C1 C2 H2A 119.6
C2 C3 C4 121.6(4)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C3 C4 C5 119.0(5)
C3 C4 H4A 120.5
C5 C4 H4A 120.5
C6 C5 C4 118.8(5)
C6 C5 H5A 120.6
C4 C5 H5A 120.6
C5 C6 C1 124.7(4)
C5 C6 C7 127.0(4)
C1 C6 C7 108.3(4)
O1 C7 C8 123.8(4)
O1 C7 C6 110.7(4)
C8 C7 C6 125.5(5)
C7 C8 C9 123.8(5)
C7 C8 H8A 118.1
C9 C8 H8A 118.1
N1 C9 C10 117.4(4)
N1 C9 C8 119.7(4)
C10 C9 C8 122.9(5)
C11 C10 C9 119.8(5)
C11 C10 H10A 120.1
C9 C10 H10A 120.1
C12 C11 C10 120.2(4)
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C13 C12 C11 120.7(5)
C13 C12 H12A 119.6
C11 C12 H12A 119.6
C12 C13 N1 117.9(5)
C12 C13 H13A 121.0
N1 C13 H13A 121.0
C15 C14 C19 114.3(4)
C15 C14 B1 128.3(4)
C19 C14 B1 116.9(4)
C16 C15 C14 121.8(5)
C16 C15 C21 115.3(4)
C14 C15 C21 122.9(4)
C15 C16 C17 123.2(5)
C15 C16 H16A 118.4
C17 C16 H16A 118.4
C18 C17 C16 115.4(5)
C18 C17 C22 123.5(5)
C16 C17 C22 121.1(5)
C19 C18 C17 124.4(5)
C19 C18 H18A 117.8
C17 C18 H18A 117.8
C18 C19 C14 121.0(4)
C18 C19 C20 118.2(5)
C14 C19 C20 120.7(4)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C15 C21 H21A 109.5
C15 C21 H21B 109.5
H21A C21 H21B 109.5
C15 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C17 C22 H22A 109.5
C17 C22 H22B 109.5
H22A C22 H22B 109.5
C17 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C24 C23 C28 114.3(4)
C24 C23 B1 126.9(4)
C28 C23 B1 118.5(4)
C25 C24 C23 123.0(5)
C25 C24 C30 114.6(5)
C23 C24 C30 122.2(4)
C24 C25 C26 121.0(5)
C24 C25 H25A 119.5
C26 C25 H25A 119.5
C27 C26 C25 117.0(5)
C27 C26 C31 123.7(5)
C25 C26 C31 119.2(5)
C26 C27 C28 124.6(5)
C26 C27 H27A 117.7
C28 C27 H27A 117.7
C27 C28 C23 119.9(5)
C27 C28 C29 118.5(5)
C23 C28 C29 121.5(5)
C28 C29 H29A 109.5
C28 C29 H29B 109.5
H29A C29 H29B 109.5
C28 C29 H29C 109.5
H29A C29 H29C 109.5
H29B C29 H29C 109.5
C24 C30 H30A 109.5
C24 C30 H30B 109.5
H30A C30 H30B 109.5
C24 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
C26 C31 H31A 109.5
C26 C31 H31B 109.5
H31A C31 H31B 109.5
C26 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.344(6)
N1 C13 1.381(6)
N1 H1A 0.98(3)
B1 O1 1.609(6)
B1 C1 1.617(7)
B1 C23 1.621(7)
B1 C14 1.632(7)
O1 C7 1.318(5)
C1 C6 1.400(6)
C1 C2 1.427(6)
C2 C3 1.380(6)
C2 H2A 0.9500
C3 C4 1.385(7)
C3 H3A 0.9500
C4 C5 1.395(6)
C4 H4A 0.9500
C5 C6 1.370(6)
C5 H5A 0.9500
C6 C7 1.489(6)
C7 C8 1.352(6)
C8 C9 1.438(6)
C8 H8A 0.9500
C9 C10 1.399(6)
C10 C11 1.386(6)
C10 H10A 0.9500
C11 C12 1.365(6)
C11 H11A 0.9500
C12 C13 1.362(7)
C12 H12A 0.9500
C13 H13A 0.9500
C14 C15 1.414(6)
C14 C19 1.448(7)
C15 C16 1.370(6)
C15 C21 1.539(7)
C16 C17 1.396(7)
C16 H16A 0.9500
C17 C18 1.369(7)
C17 C22 1.528(7)
C18 C19 1.358(6)
C18 H18A 0.9500
C19 C20 1.501(7)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 C24 1.413(7)
C23 C28 1.440(6)
C24 C25 1.384(7)
C24 C30 1.547(7)
C25 C26 1.387(7)
C25 H25A 0.9500
C26 C27 1.347(7)
C26 C31 1.510(7)
C27 C28 1.382(7)
C27 H27A 0.9500
C28 C29 1.517(7)
C29 H29A 0.9800
C29 H29B 0.9800
C29 H29C 0.9800
C30 H30A 0.9800
C30 H30B 0.9800
C30 H30C 0.9800
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 B1 O1 C7 0.6(5)
C23 B1 O1 C7 -123.3(4)
C14 B1 O1 C7 110.1(4)
O1 B1 C1 C6 2.1(5)
C23 B1 C1 C6 107.8(5)
C14 B1 C1 C6 -111.3(4)
O1 B1 C1 C2 173.1(5)
C23 B1 C1 C2 -81.2(7)
C14 B1 C1 C2 59.8(6)
C6 C1 C2 C3 -6.2(7)
B1 C1 C2 C3 -176.9(5)
C1 C2 C3 C4 5.2(7)
C2 C3 C4 C5 -2.5(7)
C3 C4 C5 C6 1.0(7)
C4 C5 C6 C1 -2.5(7)
C4 C5 C6 C7 179.5(4)
C2 C1 C6 C5 4.9(7)
B1 C1 C6 C5 177.8(4)
C2 C1 C6 C7 -176.7(4)
B1 C1 C6 C7 -3.9(5)
B1 O1 C7 C8 176.8(4)
B1 O1 C7 C6 -3.0(5)
C5 C6 C7 O1 -177.4(4)
C1 C6 C7 O1 4.4(5)
C5 C6 C7 C8 2.8(8)
C1 C6 C7 C8 -175.4(4)
O1 C7 C8 C9 -3.8(7)
C6 C7 C8 C9 176.0(4)
C13 N1 C9 C10 0.1(7)
C13 N1 C9 C8 179.7(4)
C7 C8 C9 N1 4.3(7)
C7 C8 C9 C10 -176.1(5)
N1 C9 C10 C11 -1.7(7)
C8 C9 C10 C11 178.7(4)
C9 C10 C11 C12 2.2(7)
C10 C11 C12 C13 -1.3(7)
C11 C12 C13 N1 -0.2(7)
C9 N1 C13 C12 0.8(7)
O1 B1 C14 C15 -15.2(6)
C1 B1 C14 C15 87.6(5)
C23 B1 C14 C15 -130.1(5)
O1 B1 C14 C19 173.6(4)
C1 B1 C14 C19 -83.5(5)
C23 B1 C14 C19 58.7(5)
C19 C14 C15 C16 0.9(6)
B1 C14 C15 C16 -170.4(4)
C19 C14 C15 C21 -178.6(4)
B1 C14 C15 C21 10.0(7)
C14 C15 C16 C17 -0.5(7)
C21 C15 C16 C17 179.1(4)
C15 C16 C17 C18 -0.5(7)
C15 C16 C17 C22 -179.1(5)
C16 C17 C18 C19 1.0(7)
C22 C17 C18 C19 179.6(5)
C17 C18 C19 C14 -0.6(8)
C17 C18 C19 C20 -177.6(5)
C15 C14 C19 C18 -0.4(7)
B1 C14 C19 C18 172.0(4)
C15 C14 C19 C20 176.6(4)
B1 C14 C19 C20 -11.0(6)
O1 B1 C23 C24 107.4(5)
C1 B1 C23 C24 3.8(7)
C14 B1 C23 C24 -132.2(5)
O1 B1 C23 C28 -65.4(5)
C1 B1 C23 C28 -169.0(4)
C14 B1 C23 C28 55.0(6)
C28 C23 C24 C25 3.7(7)
B1 C23 C24 C25 -169.4(4)
C28 C23 C24 C30 179.2(4)
B1 C23 C24 C30 6.2(7)
C23 C24 C25 C26 -1.0(8)
C30 C24 C25 C26 -176.9(4)
C24 C25 C26 C27 -2.2(7)
C24 C25 C26 C31 174.5(5)
C25 C26 C27 C28 2.6(8)
C31 C26 C27 C28 -174.0(5)
C26 C27 C28 C23 0.3(8)
C26 C27 C28 C29 179.5(5)
C24 C23 C28 C27 -3.3(7)
B1 C23 C28 C27 170.4(4)
C24 C23 C28 C29 177.4(4)
B1 C23 C28 C29 -8.9(7)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 0.000 240.0 22.7
2 0.000 0.500 0.500 240.0 22.7
|
1502035.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502035
loop_
_publ_author_name
'Mulzer, Michael'
'Coates, Geoffrey W.'
_publ_section_title
;
A catalytic route to ampakines and their derivatives.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1426
_journal_page_last 1428
_journal_paper_doi 10.1021/ol200111a
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C17 H15 N O2'
_chemical_formula_sum 'C17 H15 N O2'
_chemical_formula_weight 265.30
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 104.075(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.4225(4)
_cell_length_b 13.7700(7)
_cell_length_c 11.5762(5)
_cell_measurement_reflns_used 3562
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 28.39
_cell_measurement_theta_min 2.34
_cell_volume 1302.28(11)
_computing_cell_refinement 'Bruker SAINT+'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT+'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0273
_diffrn_reflns_av_sigmaI/netI 0.0304
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 10431
_diffrn_reflns_theta_full 28.39
_diffrn_reflns_theta_max 28.39
_diffrn_reflns_theta_min 2.34
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_T_max 0.9824
_exptl_absorpt_correction_T_min 0.9738
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.353
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 560
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.281
_refine_diff_density_min -0.217
_refine_diff_density_rms 0.041
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.074
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 241
_refine_ls_number_reflns 3251
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.074
_refine_ls_R_factor_all 0.0523
_refine_ls_R_factor_gt 0.0401
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.2992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0962
_refine_ls_wR_factor_ref 0.1032
_reflns_number_gt 2607
_reflns_number_total 3251
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200111a_si_002.cif
_cod_data_source_block mm1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/n
_cod_database_code 1502035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
O1 O -0.00569(10) 0.86673(6) 0.06884(8) 0.0250(2) Uani 1 1 d
O2 O 0.16441(11) 0.59263(6) 0.10914(9) 0.0316(2) Uani 1 1 d
N1 N -0.03530(12) 0.69910(7) 0.02407(9) 0.0218(2) Uani 1 1 d
C1 C 0.15956(15) 0.85325(9) 0.11050(10) 0.0215(2) Uani 1 1 d
C2 C 0.25349(16) 0.93212(9) 0.16029(12) 0.0282(3) Uani 1 1 d
H2 H 0.2010(17) 0.9943(11) 0.1631(12) 0.028(4) Uiso 1 1 d
C3 C 0.41923(17) 0.91957(10) 0.20658(13) 0.0327(3) Uani 1 1 d
H3 H 0.486(2) 0.9748(12) 0.2417(14) 0.041(4) Uiso 1 1 d
C4 C 0.49126(16) 0.82909(10) 0.20429(12) 0.0317(3) Uani 1 1 d
H4 H 0.610(2) 0.8211(12) 0.2401(14) 0.040(4) Uiso 1 1 d
C5 C 0.39626(16) 0.75007(10) 0.15802(11) 0.0266(3) Uani 1 1 d
H5 H 0.4445(18) 0.6852(11) 0.1599(13) 0.031(4) Uiso 1 1 d
C6 C 0.22863(14) 0.76131(8) 0.11062(10) 0.0208(2) Uani 1 1 d
C7 C 0.12018(15) 0.67532(8) 0.07929(10) 0.0218(2) Uani 1 1 d
C8 C -0.17520(15) 0.63312(9) 0.00624(11) 0.0226(3) Uani 1 1 d
H8 H -0.1519(17) 0.5755(11) -0.0317(12) 0.027(4) Uiso 1 1 d
C9 C -0.31155(16) 0.69441(10) -0.07363(12) 0.0281(3) Uani 1 1 d
H9B H -0.4188(19) 0.6783(11) -0.0607(13) 0.029(4) Uiso 1 1 d
H9A H -0.3142(18) 0.6801(11) -0.1572(14) 0.035(4) Uiso 1 1 d
C10 C -0.26219(16) 0.79963(10) -0.04303(13) 0.0293(3) Uani 1 1 d
H10B H -0.3116(19) 0.8443(12) -0.1091(14) 0.037(4) Uiso 1 1 d
H10A H -0.2931(18) 0.8200(11) 0.0310(14) 0.033(4) Uiso 1 1 d
C11 C -0.07751(15) 0.79694(9) -0.01900(11) 0.0235(3) Uani 1 1 d
H11 H -0.0322(16) 0.8097(10) -0.0908(12) 0.021(3) Uiso 1 1 d
C12 C -0.21478(14) 0.60362(8) 0.12198(10) 0.0203(2) Uani 1 1 d
C13 C -0.16466(15) 0.65674(9) 0.22640(11) 0.0246(3) Uani 1 1 d
H13 H -0.0986(17) 0.7152(10) 0.2269(12) 0.025(3) Uiso 1 1 d
C14 C -0.20716(16) 0.62725(10) 0.32943(12) 0.0285(3) Uani 1 1 d
H14 H -0.1685(19) 0.6653(11) 0.4033(14) 0.035(4) Uiso 1 1 d
C15 C -0.30167(16) 0.54558(10) 0.32904(12) 0.0297(3) Uani 1 1 d
H15 H -0.3327(19) 0.5245(12) 0.4006(14) 0.038(4) Uiso 1 1 d
C16 C -0.35311(16) 0.49244(10) 0.22522(12) 0.0290(3) Uani 1 1 d
H16 H -0.4180(19) 0.4353(13) 0.2251(14) 0.040(4) Uiso 1 1 d
C17 C -0.30888(15) 0.52089(9) 0.12267(11) 0.0243(3) Uani 1 1 d
H17 H -0.3423(17) 0.4823(11) 0.0512(12) 0.028(4) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0247(4) 0.0183(4) 0.0310(5) -0.0040(3) 0.0048(3) 0.0007(3)
O2 0.0321(5) 0.0178(4) 0.0445(6) 0.0001(4) 0.0084(4) 0.0020(4)
N1 0.0241(5) 0.0174(5) 0.0244(5) -0.0010(4) 0.0068(4) -0.0027(4)
C1 0.0240(6) 0.0204(6) 0.0211(6) 0.0008(4) 0.0073(4) -0.0005(4)
C2 0.0333(7) 0.0191(6) 0.0327(7) -0.0026(5) 0.0087(5) -0.0032(5)
C3 0.0327(7) 0.0277(7) 0.0365(7) -0.0036(6) 0.0060(6) -0.0093(6)
C4 0.0238(6) 0.0340(7) 0.0364(7) 0.0010(6) 0.0053(5) -0.0039(5)
C5 0.0262(6) 0.0257(6) 0.0293(6) 0.0009(5) 0.0093(5) 0.0013(5)
C6 0.0246(6) 0.0195(6) 0.0200(6) -0.0006(4) 0.0084(4) -0.0012(4)
C7 0.0258(6) 0.0187(6) 0.0227(6) -0.0024(4) 0.0096(5) -0.0001(4)
C8 0.0254(6) 0.0192(6) 0.0231(6) -0.0036(5) 0.0056(5) -0.0041(5)
C9 0.0288(7) 0.0297(7) 0.0229(6) 0.0011(5) 0.0007(5) -0.0060(5)
C10 0.0272(6) 0.0263(7) 0.0308(7) 0.0041(5) 0.0005(5) -0.0002(5)
C11 0.0285(6) 0.0189(6) 0.0225(6) 0.0010(4) 0.0054(5) -0.0020(5)
C12 0.0190(5) 0.0182(5) 0.0227(6) 0.0005(4) 0.0032(4) 0.0009(4)
C13 0.0249(6) 0.0227(6) 0.0263(6) -0.0039(5) 0.0065(5) -0.0039(5)
C14 0.0306(7) 0.0308(7) 0.0246(6) -0.0048(5) 0.0078(5) -0.0010(5)
C15 0.0315(7) 0.0322(7) 0.0277(7) 0.0033(5) 0.0115(5) -0.0003(5)
C16 0.0281(6) 0.0250(6) 0.0344(7) 0.0012(5) 0.0090(5) -0.0052(5)
C17 0.0242(6) 0.0226(6) 0.0247(6) -0.0028(5) 0.0029(5) -0.0032(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C11 112.27(9)
C7 N1 C11 121.09(10)
C7 N1 C8 124.85(10)
C11 N1 C8 114.01(10)
O1 C1 C2 117.97(11)
O1 C1 C6 120.77(10)
C2 C1 C6 121.10(11)
C3 C2 C1 119.04(12)
C3 C2 H2 121.7(8)
C1 C2 H2 119.3(8)
C2 C3 C4 120.70(12)
C2 C3 H3 119.4(10)
C4 C3 H3 119.9(10)
C5 C4 C3 120.02(12)
C5 C4 H4 120.4(10)
C3 C4 H4 119.5(10)
C4 C5 C6 120.12(12)
C4 C5 H5 120.8(9)
C6 C5 H5 119.0(9)
C1 C6 C5 118.95(11)
C1 C6 C7 119.49(10)
C5 C6 C7 120.77(11)
O2 C7 N1 123.63(11)
O2 C7 C6 123.15(11)
N1 C7 C6 112.97(10)
N1 C8 C12 112.67(9)
N1 C8 C9 101.65(9)
C12 C8 C9 112.72(10)
N1 C8 H8 109.5(9)
C12 C8 H8 107.5(9)
C9 C8 H8 112.8(8)
C10 C9 C8 105.07(10)
C10 C9 H9B 113.0(9)
C8 C9 H9B 111.5(9)
C10 C9 H9A 111.0(9)
C8 C9 H9A 108.4(9)
H9B C9 H9A 107.8(12)
C11 C10 C9 103.27(11)
C11 C10 H10B 112.2(9)
C9 C10 H10B 111.8(9)
C11 C10 H10A 108.7(9)
C9 C10 H10A 110.8(9)
H10B C10 H10A 109.9(13)
O1 C11 N1 110.83(9)
O1 C11 C10 110.75(10)
N1 C11 C10 103.95(10)
O1 C11 H11 106.9(8)
N1 C11 H11 109.5(8)
C10 C11 H11 114.9(7)
C13 C12 C17 118.71(11)
C13 C12 C8 122.96(11)
C17 C12 C8 118.31(10)
C14 C13 C12 120.49(12)
C14 C13 H13 120.1(8)
C12 C13 H13 119.4(8)
C15 C14 C13 120.41(12)
C15 C14 H14 120.3(9)
C13 C14 H14 119.3(9)
C14 C15 C16 119.56(12)
C14 C15 H15 121.1(9)
C16 C15 H15 119.4(9)
C15 C16 C17 120.16(12)
C15 C16 H16 119.6(9)
C17 C16 H16 120.2(9)
C16 C17 C12 120.66(11)
C16 C17 H17 119.7(8)
C12 C17 H17 119.6(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3703(14)
O1 C11 1.4228(14)
O2 C7 1.2215(14)
N1 C7 1.3504(15)
N1 C11 1.4504(15)
N1 C8 1.4623(15)
C1 C2 1.3841(17)
C1 C6 1.3932(16)
C2 C3 1.3791(19)
C2 H2 0.968(15)
C3 C4 1.389(2)
C3 H3 0.974(17)
C4 C5 1.3793(18)
C4 H4 0.988(16)
C5 C6 1.3935(17)
C5 H5 0.979(15)
C6 C7 1.4855(16)
C8 C12 1.5128(16)
C8 C9 1.5393(18)
C8 H8 0.951(15)
C9 C10 1.5251(18)
C9 H9B 0.976(15)
C9 H9A 0.982(15)
C10 C11 1.5126(17)
C10 H10B 0.991(16)
C10 H10A 0.995(16)
C11 H11 1.011(14)
C12 C13 1.3879(16)
C12 C17 1.3889(16)
C13 C14 1.3867(18)
C13 H13 0.978(15)
C14 C15 1.3771(19)
C14 H14 0.988(16)
C15 C16 1.3836(19)
C15 H15 0.971(16)
C16 C17 1.3844(18)
C16 H16 0.958(17)
C17 H17 0.965(14)
|
1502036.cif | #------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/20/1502036.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502036
loop_
_publ_author_name
'Chen, Jiun-Jia'
'Li, Kuan-Ting'
'Yang, Ding-Yah'
_publ_section_title
;
Synthesis of coumarin/phenanthridine-fused heterocycles and their
photochemical and thermochromic properties.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1658
_journal_page_last 1661
_journal_paper_doi 10.1021/ol200117b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C24 H19 N3 O2'
_chemical_formula_sum 'C24 H19 N3 O2'
_chemical_formula_weight 381.42
_space_group_IT_number 15
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 15
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 100.169(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 21.849(3)
_cell_length_b 12.3571(15)
_cell_length_c 16.732(2)
_cell_measurement_reflns_used 3865
_cell_measurement_temperature 297(2)
_cell_measurement_theta_max 25.747
_cell_measurement_theta_min 2.353
_cell_volume 4446.5(10)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0361
_diffrn_reflns_av_sigmaI/netI 0.0313
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 12359
_diffrn_reflns_theta_full 26.05
_diffrn_reflns_theta_max 26.05
_diffrn_reflns_theta_min 1.89
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.074
_exptl_absorpt_correction_T_max 1.000000
_exptl_absorpt_correction_T_min 0.767743
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details empirical
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.140
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 1600
_exptl_crystal_size_max 0.55
_exptl_crystal_size_mid 0.52
_exptl_crystal_size_min 0.41
_platon_squeeze_details ' '
_refine_diff_density_max 0.210
_refine_diff_density_min -0.188
_refine_diff_density_rms 0.043
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.132
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 264
_refine_ls_number_reflns 4380
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.132
_refine_ls_R_factor_all 0.0892
_refine_ls_R_factor_gt 0.0596
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+1.8507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1889
_refine_ls_wR_factor_ref 0.2014
_reflns_number_gt 2667
_reflns_number_total 4380
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200117b_si_001.cif
_cod_data_source_block jj001m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'constro' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.
Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius
;
_cod_original_cell_volume 4446.5(9)
_cod_original_sg_symbol_H-M 'C 2/c'
_cod_database_code 1502036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.44111(8) 0.58910(15) 0.03098(10) 0.0611(5) Uani 1 1 d .
O2 O 0.47672(9) 0.48237(15) 0.13298(11) 0.0658(5) Uani 1 1 d .
N1 N 0.37529(12) 0.8008(2) -0.20421(14) 0.0805(8) Uani 1 1 d .
N2 N 0.37850(11) 0.71704(18) 0.42329(12) 0.0624(6) Uani 1 1 d .
N3 N 0.28467(13) 0.4962(2) 0.39655(15) 0.0797(7) Uani 1 1 d .
C1 C 0.40346(11) 0.6728(2) -0.00395(15) 0.0536(6) Uani 1 1 d .
C2 C 0.40805(12) 0.6956(2) -0.08327(15) 0.0603(7) Uani 1 1 d .
H2A H 0.4358 0.6571 -0.1087 0.072 Uiso 1 1 calc R
C3 C 0.37139(13) 0.7759(2) -0.12523(15) 0.0617(7) Uani 1 1 d .
C4 C 0.33043(14) 0.8317(2) -0.08335(17) 0.0716(8) Uani 1 1 d .
H4A H 0.3049 0.8855 -0.1102 0.086 Uiso 1 1 calc R
C5 C 0.32749(13) 0.8088(2) -0.00469(16) 0.0641(7) Uani 1 1 d .
H5A H 0.3003 0.8481 0.0210 0.077 Uiso 1 1 calc R
C6 C 0.36398(11) 0.7281(2) 0.03901(15) 0.0537(6) Uani 1 1 d .
C7 C 0.36573(11) 0.70148(19) 0.12356(14) 0.0491(6) Uani 1 1 d .
C8 C 0.33215(11) 0.7575(2) 0.17456(15) 0.0536(6) Uani 1 1 d .
H8A H 0.3061 0.8138 0.1532 0.064 Uiso 1 1 calc R
C9 C 0.33682(11) 0.73110(19) 0.25613(15) 0.0513(6) Uani 1 1 d .
C10 C 0.30476(11) 0.7919(2) 0.31218(14) 0.0533(6) Uani 1 1 d .
C11 C 0.25501(13) 0.8590(2) 0.28577(17) 0.0648(7) Uani 1 1 d .
H11A H 0.2389 0.8624 0.2305 0.078 Uiso 1 1 calc R
C12 C 0.22843(15) 0.9209(2) 0.33861(19) 0.0745(8) Uani 1 1 d .
H12A H 0.1951 0.9661 0.3192 0.089 Uiso 1 1 calc R
C13 C 0.25152(16) 0.9155(2) 0.42028(19) 0.0742(8) Uani 1 1 d .
H13A H 0.2340 0.9579 0.4563 0.089 Uiso 1 1 calc R
C14 C 0.29997(15) 0.8487(2) 0.44903(17) 0.0707(8) Uani 1 1 d .
H14A H 0.3149 0.8455 0.5046 0.085 Uiso 1 1 calc R
C15 C 0.32784(13) 0.7844(2) 0.39632(15) 0.0575(6) Uani 1 1 d .
C16 C 0.37930(12) 0.6195(2) 0.37648(15) 0.0594(7) Uani 1 1 d .
H16A H 0.4183 0.5812 0.3962 0.071 Uiso 1 1 calc R
C17 C 0.37681(11) 0.6466(2) 0.28794(14) 0.0512(6) Uani 1 1 d .
C18 C 0.41029(11) 0.59163(19) 0.23946(14) 0.0513(6) Uani 1 1 d .
H18A H 0.4366 0.5360 0.2614 0.062 Uiso 1 1 calc R
C19 C 0.40559(10) 0.61744(18) 0.15816(14) 0.0474(6) Uani 1 1 d .
C20 C 0.44298(11) 0.5577(2) 0.10948(14) 0.0517(6) Uani 1 1 d .
C21 C 0.41540(18) 0.7419(3) -0.2475(2) 0.1033(13) Uani 1 1 d .
H21A H 0.4575 0.7473 -0.2192 0.155 Uiso 1 1 calc R
H21B H 0.4125 0.7715 -0.3011 0.155 Uiso 1 1 calc R
H21C H 0.4031 0.6672 -0.2513 0.155 Uiso 1 1 calc R
C22 C 0.33780(19) 0.8866(3) -0.2468(2) 0.1007(11) Uani 1 1 d .
H22A H 0.2956 0.8790 -0.2387 0.151 Uiso 1 1 calc R
H22B H 0.3392 0.8823 -0.3037 0.151 Uiso 1 1 calc R
H22C H 0.3538 0.9554 -0.2261 0.151 Uiso 1 1 calc R
C23 C 0.40118(16) 0.7045(3) 0.51030(16) 0.0805(9) Uani 1 1 d .
H23A H 0.3988 0.7728 0.5370 0.121 Uiso 1 1 calc R
H23B H 0.4436 0.6803 0.5190 0.121 Uiso 1 1 calc R
H23C H 0.3761 0.6523 0.5321 0.121 Uiso 1 1 calc R
C24 C 0.32638(14) 0.5474(2) 0.38770(15) 0.0598(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0608(11) 0.0732(12) 0.0513(11) -0.0033(8) 0.0158(8) 0.0168(9)
O2 0.0656(11) 0.0711(12) 0.0588(11) -0.0099(9) 0.0054(8) 0.0224(10)
N1 0.0925(19) 0.0979(19) 0.0537(14) 0.0100(13) 0.0203(13) 0.0196(15)
N2 0.0709(14) 0.0698(14) 0.0446(12) -0.0027(10) 0.0049(10) 0.0042(12)
N3 0.0929(19) 0.0877(18) 0.0627(16) -0.0035(13) 0.0249(14) -0.0092(16)
C1 0.0507(14) 0.0587(15) 0.0525(14) -0.0067(11) 0.0117(11) 0.0041(12)
C2 0.0613(16) 0.0705(17) 0.0527(15) -0.0063(13) 0.0195(12) 0.0035(14)
C3 0.0639(16) 0.0738(18) 0.0487(15) -0.0019(13) 0.0138(12) 0.0007(14)
C4 0.0786(19) 0.085(2) 0.0522(16) 0.0073(14) 0.0137(13) 0.0201(16)
C5 0.0646(17) 0.0748(18) 0.0548(16) 0.0007(13) 0.0155(12) 0.0183(14)
C6 0.0522(14) 0.0632(15) 0.0463(14) -0.0040(11) 0.0108(10) 0.0054(12)
C7 0.0449(13) 0.0580(14) 0.0451(13) -0.0032(11) 0.0101(10) 0.0006(11)
C8 0.0512(14) 0.0601(15) 0.0507(14) 0.0010(11) 0.0125(11) 0.0109(12)
C9 0.0493(13) 0.0570(14) 0.0489(14) -0.0029(11) 0.0127(10) 0.0012(11)
C10 0.0525(14) 0.0601(15) 0.0495(14) -0.0014(11) 0.0154(11) 0.0022(12)
C11 0.0679(17) 0.0761(18) 0.0546(15) 0.0013(13) 0.0223(13) 0.0168(15)
C12 0.077(2) 0.0773(19) 0.076(2) -0.0004(15) 0.0312(16) 0.0193(16)
C13 0.092(2) 0.0706(18) 0.069(2) -0.0083(15) 0.0386(16) 0.0094(17)
C14 0.093(2) 0.0721(18) 0.0522(16) -0.0069(13) 0.0278(15) -0.0047(17)
C15 0.0685(16) 0.0573(14) 0.0490(14) -0.0042(12) 0.0169(12) -0.0062(13)
C16 0.0572(15) 0.0714(17) 0.0494(15) 0.0026(12) 0.0092(11) 0.0117(13)
C17 0.0476(13) 0.0609(15) 0.0448(13) 0.0002(11) 0.0067(10) 0.0045(12)
C18 0.0473(13) 0.0546(14) 0.0512(14) 0.0005(11) 0.0062(10) 0.0045(11)
C19 0.0419(12) 0.0487(13) 0.0515(14) -0.0053(11) 0.0076(10) 0.0010(10)
C20 0.0453(13) 0.0592(15) 0.0493(14) -0.0100(12) 0.0052(10) -0.0004(12)
C21 0.107(3) 0.147(3) 0.064(2) 0.009(2) 0.0381(19) 0.030(2)
C22 0.114(3) 0.124(3) 0.067(2) 0.022(2) 0.0245(19) 0.015(2)
C23 0.095(2) 0.097(2) 0.0449(16) 0.0006(15) -0.0003(14) 0.0022(18)
C24 0.0677(17) 0.0669(16) 0.0467(15) 0.0020(12) 0.0158(12) 0.0049(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 O1 C1 122.27(18)
C3 N1 C22 120.8(3)
C3 N1 C21 121.3(3)
C22 N1 C21 117.9(3)
C15 N2 C16 114.1(2)
C15 N2 C23 119.7(2)
C16 N2 C23 114.8(2)
C2 C1 O1 114.9(2)
C2 C1 C6 123.6(2)
O1 C1 C6 121.6(2)
C1 C2 C3 120.0(2)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
N1 C3 C2 121.3(2)
N1 C3 C4 121.3(3)
C2 C3 C4 117.4(2)
C5 C4 C3 121.4(3)
C5 C4 H4A 119.3
C3 C4 H4A 119.3
C4 C5 C6 122.3(2)
C4 C5 H5A 118.8
C6 C5 H5A 118.8
C1 C6 C5 115.3(2)
C1 C6 C7 118.7(2)
C5 C6 C7 126.0(2)
C19 C7 C8 117.7(2)
C19 C7 C6 118.4(2)
C8 C7 C6 123.8(2)
C9 C8 C7 121.8(2)
C9 C8 H8A 119.1
C7 C8 H8A 119.1
C8 C9 C17 118.7(2)
C8 C9 C10 123.1(2)
C17 C9 C10 118.2(2)
C15 C10 C11 118.8(2)
C15 C10 C9 118.4(2)
C11 C10 C9 122.7(2)
C12 C11 C10 121.9(3)
C12 C11 H11A 119.0
C10 C11 H11A 119.0
C11 C12 C13 119.4(3)
C11 C12 H12A 120.3
C13 C12 H12A 120.3
C14 C13 C12 120.5(3)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C13 C14 C15 121.2(3)
C13 C14 H14A 119.4
C15 C14 H14A 119.4
C10 C15 N2 119.0(2)
C10 C15 C14 118.1(3)
N2 C15 C14 122.8(2)
N2 C16 C17 110.3(2)
N2 C16 C24 110.3(2)
C17 C16 C24 111.1(2)
N2 C16 H16A 108.4
C17 C16 H16A 108.4
C24 C16 H16A 108.4
C18 C17 C9 120.5(2)
C18 C17 C16 122.8(2)
C9 C17 C16 116.7(2)
C17 C18 C19 121.0(2)
C17 C18 H18A 119.5
C19 C18 H18A 119.5
C18 C19 C7 120.4(2)
C18 C19 C20 118.9(2)
C7 C19 C20 120.7(2)
O2 C20 O1 116.5(2)
O2 C20 C19 125.4(2)
O1 C20 C19 118.1(2)
N1 C21 H21A 109.5
N1 C21 H21B 109.5
H21A C21 H21B 109.5
N1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 H22A 109.5
N1 C22 H22B 109.5
H22A C22 H22B 109.5
N1 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
N2 C23 H23A 109.5
N2 C23 H23B 109.5
H23A C23 H23B 109.5
N2 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
N3 C24 C16 177.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C20 1.363(3)
O1 C1 1.385(3)
O2 C20 1.209(3)
N1 C3 1.374(3)
N1 C22 1.448(4)
N1 C21 1.431(4)
N2 C15 1.395(3)
N2 C16 1.439(3)
N2 C23 1.461(3)
N3 C24 1.140(3)
C1 C2 1.378(3)
C1 C6 1.395(3)
C2 C3 1.386(4)
C2 H2A 0.9300
C3 C4 1.411(4)
C4 C5 1.359(4)
C4 H4A 0.9300
C5 C6 1.400(4)
C5 H5A 0.9300
C6 C7 1.446(3)
C7 C19 1.412(3)
C7 C8 1.402(3)
C8 C9 1.389(3)
C8 H8A 0.9300
C9 C17 1.405(3)
C9 C10 1.472(3)
C10 C15 1.412(3)
C10 C11 1.376(4)
C11 C12 1.374(4)
C11 H11A 0.9300
C12 C13 1.372(4)
C12 H12A 0.9300
C13 C14 1.362(4)
C13 H13A 0.9300
C14 C15 1.403(4)
C14 H14A 0.9300
C16 C17 1.510(3)
C16 C24 1.498(4)
C16 H16A 0.9800
C17 C18 1.365(3)
C18 C19 1.383(3)
C18 H18A 0.9300
C19 C20 1.453(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.020 486 111 ' '
2 0.000 0.500 0.147 486 111 ' '
|
1502037.cif | #------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/20/1502037.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502037
loop_
_publ_author_name
'Chen, Jiun-Jia'
'Li, Kuan-Ting'
'Yang, Ding-Yah'
_publ_section_title
;
Synthesis of coumarin/phenanthridine-fused heterocycles and their
photochemical and thermochromic properties.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1658
_journal_page_last 1661
_journal_paper_doi 10.1021/ol200117b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C23 H20 N2 O2'
_chemical_formula_sum 'C23 H20 N2 O2'
_chemical_formula_weight 356.41
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 116.038(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 14.9549(18)
_cell_length_b 17.960(2)
_cell_length_c 14.7060(17)
_cell_measurement_reflns_used 3615
_cell_measurement_temperature 297(2)
_cell_measurement_theta_max 23.872
_cell_measurement_theta_min 2.721
_cell_volume 3549.0(7)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 297(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0601
_diffrn_reflns_av_sigmaI/netI 0.0647
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 20103
_diffrn_reflns_theta_full 26.07
_diffrn_reflns_theta_max 26.07
_diffrn_reflns_theta_min 1.89
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.086
_exptl_absorpt_correction_T_max 0.9872
_exptl_absorpt_correction_T_min 0.9551
_exptl_absorpt_correction_type empirical
_exptl_absorpt_process_details empirical
_exptl_crystal_colour orange
_exptl_crystal_density_diffrn 1.334
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 1504
_exptl_crystal_size_max 0.54
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.270
_refine_diff_density_min -0.248
_refine_diff_density_rms 0.048
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 487
_refine_ls_number_reflns 6987
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.048
_refine_ls_R_factor_all 0.1261
_refine_ls_R_factor_gt 0.0603
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1598
_refine_ls_wR_factor_ref 0.1928
_reflns_number_gt 3533
_reflns_number_total 6987
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200117b_si_002.cif
_cod_data_source_block jj008m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'constro' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.
Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius
;
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1502037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.37037(15) 0.62497(11) 0.37922(14) 0.0559(6) Uani 1 1 d .
O2 O 0.51902(16) 0.57459(13) 0.43761(15) 0.0674(6) Uani 1 1 d .
N1 N 0.0543(2) 0.73263(16) 0.2900(2) 0.0665(8) Uani 1 1 d .
N2 N 0.4958(2) 0.38040(16) 0.0603(2) 0.0700(8) Uani 1 1 d .
C1 C 0.2745(2) 0.63523(15) 0.3028(2) 0.0451(7) Uani 1 1 d .
C2 C 0.2150(2) 0.67761(16) 0.3314(2) 0.0522(8) Uani 1 1 d .
H2A H 0.2409 0.6986 0.3957 0.063 Uiso 1 1 calc R
C3 C 0.1153(2) 0.68927(16) 0.2638(2) 0.0516(7) Uani 1 1 d .
C4 C 0.0817(2) 0.65650(17) 0.1677(2) 0.0574(8) Uani 1 1 d .
H4A H 0.0155 0.6626 0.1210 0.069 Uiso 1 1 calc R
C5 C 0.1438(2) 0.61594(16) 0.1410(2) 0.0521(8) Uani 1 1 d .
H5A H 0.1190 0.5959 0.0762 0.062 Uiso 1 1 calc R
C6 C 0.2440(2) 0.60366(15) 0.2085(2) 0.0426(7) Uani 1 1 d .
C7 C 0.3147(2) 0.56021(15) 0.1865(2) 0.0423(7) Uani 1 1 d .
C8 C 0.4104(2) 0.54959(14) 0.2657(2) 0.0424(7) Uani 1 1 d .
C9 C 0.4385(2) 0.58195(17) 0.3650(2) 0.0510(7) Uani 1 1 d .
C10 C 0.4803(2) 0.50802(16) 0.2501(2) 0.0472(7) Uani 1 1 d .
H10A H 0.5432 0.5014 0.3032 0.057 Uiso 1 1 calc R
C11 C 0.4587(2) 0.47633(15) 0.1576(2) 0.0461(7) Uani 1 1 d .
C12 C 0.3637(2) 0.48672(15) 0.0763(2) 0.0452(7) Uani 1 1 d .
C13 C 0.2933(2) 0.52785(15) 0.0925(2) 0.0464(7) Uani 1 1 d .
H13A H 0.2302 0.5341 0.0394 0.056 Uiso 1 1 calc R
C14 C 0.5360(2) 0.43202(18) 0.1428(2) 0.0589(8) Uani 1 1 d .
H14A H 0.5802 0.4660 0.1310 0.071 Uiso 1 1 calc R
H14B H 0.5753 0.4048 0.2045 0.071 Uiso 1 1 calc R
C15 C 0.4123(2) 0.40026(17) -0.0269(2) 0.0544(8) Uani 1 1 d .
C16 C 0.3443(2) 0.45285(16) -0.0214(2) 0.0485(7) Uani 1 1 d .
C17 C 0.2592(2) 0.46892(19) -0.1095(2) 0.0600(9) Uani 1 1 d .
H17A H 0.2139 0.5032 -0.1067 0.072 Uiso 1 1 calc R
C18 C 0.2399(3) 0.4357(2) -0.2005(3) 0.0726(10) Uani 1 1 d .
H18A H 0.1830 0.4482 -0.2585 0.087 Uiso 1 1 calc R
C19 C 0.3057(3) 0.3838(2) -0.2047(3) 0.0771(11) Uani 1 1 d .
H19A H 0.2922 0.3602 -0.2656 0.092 Uiso 1 1 calc R
C20 C 0.3909(3) 0.36646(19) -0.1198(3) 0.0698(10) Uani 1 1 d .
H20A H 0.4350 0.3317 -0.1241 0.084 Uiso 1 1 calc R
C21 C 0.0938(3) 0.7685(2) 0.3886(3) 0.0817(11) Uani 1 1 d .
H21A H 0.1652 0.7690 0.4175 0.123 Uiso 1 1 calc R
H21B H 0.0729 0.7415 0.4322 0.123 Uiso 1 1 calc R
H21C H 0.0695 0.8187 0.3810 0.123 Uiso 1 1 calc R
C22 C -0.0529(3) 0.7268(2) 0.2349(3) 0.0770(10) Uani 1 1 d .
H22A H -0.0699 0.7023 0.1714 0.115 Uiso 1 1 calc R
H22B H -0.0816 0.7757 0.2228 0.115 Uiso 1 1 calc R
H22C H -0.0782 0.6985 0.2739 0.115 Uiso 1 1 calc R
C23 C 0.5694(3) 0.3313(2) 0.0524(3) 0.0940(14) Uani 1 1 d .
H23A H 0.5373 0.2984 -0.0042 0.141 Uiso 1 1 calc R
H23B H 0.6013 0.3026 0.1134 0.141 Uiso 1 1 calc R
H23C H 0.6184 0.3605 0.0429 0.141 Uiso 1 1 calc R
O3 O 0.00253(14) 0.50406(13) 0.25454(15) 0.0610(6) Uani 1 1 d .
O4 O -0.05476(17) 0.46483(15) 0.09814(17) 0.0874(9) Uani 1 1 d .
N3 N 0.1023(2) 0.61007(17) 0.5801(2) 0.0732(8) Uani 1 1 d .
N4 N 0.2985(2) 0.25658(14) 0.11173(18) 0.0590(7) Uani 1 1 d .
C24 C 0.0800(2) 0.51358(16) 0.3513(2) 0.0485(7) Uani 1 1 d .
C25 C 0.0546(2) 0.55498(16) 0.4150(2) 0.0533(8) Uani 1 1 d .
H25A H -0.0096 0.5738 0.3921 0.064 Uiso 1 1 calc R
C26 C 0.1251(2) 0.56883(16) 0.5141(2) 0.0539(8) Uani 1 1 d .
C27 C 0.2208(2) 0.53949(17) 0.5429(2) 0.0579(8) Uani 1 1 d .
H27A H 0.2701 0.5483 0.6080 0.070 Uiso 1 1 calc R
C28 C 0.2433(2) 0.49834(17) 0.4775(2) 0.0524(8) Uani 1 1 d .
H28A H 0.3076 0.4799 0.4997 0.063 Uiso 1 1 calc R
C29 C 0.1731(2) 0.48298(15) 0.3782(2) 0.0433(7) Uani 1 1 d .
C30 C 0.1906(2) 0.43965(15) 0.3044(2) 0.0420(7) Uani 1 1 d .
C31 C 0.1121(2) 0.43309(15) 0.2063(2) 0.0448(7) Uani 1 1 d .
C32 C 0.0154(2) 0.46722(19) 0.1805(2) 0.0586(8) Uani 1 1 d .
C33 C 0.1246(2) 0.39248(16) 0.1323(2) 0.0497(7) Uani 1 1 d .
H33A H 0.0721 0.3889 0.0679 0.060 Uiso 1 1 calc R
C34 C 0.2125(2) 0.35769(16) 0.1523(2) 0.0457(7) Uani 1 1 d .
C35 C 0.2930(2) 0.36363(15) 0.2498(2) 0.0418(7) Uani 1 1 d .
C36 C 0.2802(2) 0.40400(15) 0.3238(2) 0.0427(7) Uani 1 1 d .
H36A H 0.3328 0.4074 0.3882 0.051 Uiso 1 1 calc R
C37 C 0.2261(2) 0.31552(17) 0.0709(2) 0.0549(8) Uani 1 1 d .
H37A H 0.1628 0.2944 0.0242 0.066 Uiso 1 1 calc R
H37B H 0.2474 0.3497 0.0332 0.066 Uiso 1 1 calc R
C38 C 0.3878(2) 0.27486(16) 0.1957(2) 0.0501(7) Uani 1 1 d .
C39 C 0.3873(2) 0.32691(15) 0.2671(2) 0.0437(7) Uani 1 1 d .
C40 C 0.4757(2) 0.34165(16) 0.3520(2) 0.0500(7) Uani 1 1 d .
H40A H 0.4758 0.3760 0.3994 0.060 Uiso 1 1 calc R
C41 C 0.5640(2) 0.30654(18) 0.3680(2) 0.0573(8) Uani 1 1 d .
H41A H 0.6226 0.3174 0.4251 0.069 Uiso 1 1 calc R
C42 C 0.5635(3) 0.25562(19) 0.2985(3) 0.0655(9) Uani 1 1 d .
H42A H 0.6222 0.2313 0.3090 0.079 Uiso 1 1 calc R
C43 C 0.4771(3) 0.24013(19) 0.2133(3) 0.0655(9) Uani 1 1 d .
H43A H 0.4785 0.2058 0.1666 0.079 Uiso 1 1 calc R
C44 C 0.0031(3) 0.6392(2) 0.5488(3) 0.0792(11) Uani 1 1 d .
H44A H -0.0402 0.6197 0.4834 0.119 Uiso 1 1 calc R
H44B H 0.0047 0.6926 0.5454 0.119 Uiso 1 1 calc R
H44C H -0.0210 0.6248 0.5969 0.119 Uiso 1 1 calc R
C45 C 0.1773(3) 0.6335(2) 0.6767(3) 0.0946(14) Uani 1 1 d .
H45A H 0.2396 0.6106 0.6890 0.142 Uiso 1 1 calc R
H45B H 0.1584 0.6189 0.7287 0.142 Uiso 1 1 calc R
H45C H 0.1841 0.6867 0.6772 0.142 Uiso 1 1 calc R
C46 C 0.3017(3) 0.2091(2) 0.0330(3) 0.0831(12) Uani 1 1 d .
H46A H 0.3507 0.1708 0.0634 0.125 Uiso 1 1 calc R
H46B H 0.3190 0.2384 -0.0116 0.125 Uiso 1 1 calc R
H46C H 0.2376 0.1867 -0.0049 0.125 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0444(13) 0.0699(14) 0.0440(12) -0.0111(10) 0.0108(11) 0.0017(10)
O2 0.0469(14) 0.0927(17) 0.0452(12) -0.0084(11) 0.0043(11) 0.0065(12)
N1 0.0569(18) 0.0774(19) 0.0617(17) -0.0105(15) 0.0228(15) 0.0150(15)
N2 0.073(2) 0.0707(19) 0.0567(17) -0.0055(15) 0.0200(16) 0.0248(15)
C1 0.0404(17) 0.0480(17) 0.0402(16) 0.0017(13) 0.0115(14) -0.0001(13)
C2 0.052(2) 0.0545(18) 0.0446(17) -0.0040(15) 0.0166(16) -0.0006(15)
C3 0.0517(19) 0.0504(18) 0.0497(17) 0.0023(15) 0.0195(16) 0.0044(14)
C4 0.0484(19) 0.065(2) 0.0465(18) -0.0017(16) 0.0098(16) 0.0092(16)
C5 0.0469(19) 0.0561(19) 0.0443(17) -0.0058(14) 0.0118(16) 0.0036(14)
C6 0.0428(17) 0.0417(16) 0.0394(15) -0.0007(13) 0.0145(14) -0.0010(13)
C7 0.0415(17) 0.0439(16) 0.0392(15) 0.0024(13) 0.0156(14) -0.0053(13)
C8 0.0423(17) 0.0415(16) 0.0387(15) 0.0022(13) 0.0136(14) -0.0026(13)
C9 0.0432(19) 0.0552(19) 0.0496(19) 0.0011(15) 0.0158(17) -0.0024(15)
C10 0.0396(17) 0.0515(18) 0.0442(16) 0.0024(14) 0.0124(14) -0.0004(13)
C11 0.0417(17) 0.0477(17) 0.0476(17) 0.0030(14) 0.0184(15) 0.0013(13)
C12 0.0449(18) 0.0465(17) 0.0446(16) -0.0005(13) 0.0201(15) -0.0039(13)
C13 0.0436(17) 0.0504(17) 0.0407(16) -0.0002(13) 0.0142(14) 0.0002(13)
C14 0.054(2) 0.064(2) 0.0558(19) 0.0048(17) 0.0211(17) 0.0071(16)
C15 0.056(2) 0.0530(19) 0.0542(19) -0.0015(15) 0.0236(17) -0.0014(15)
C16 0.0489(19) 0.0518(18) 0.0477(17) -0.0049(14) 0.0238(16) -0.0045(14)
C17 0.0441(19) 0.082(2) 0.0501(19) -0.0112(17) 0.0172(17) 0.0007(16)
C18 0.054(2) 0.100(3) 0.055(2) -0.018(2) 0.0158(18) 0.000(2)
C19 0.070(3) 0.095(3) 0.062(2) -0.030(2) 0.025(2) -0.002(2)
C20 0.069(2) 0.074(2) 0.065(2) -0.0167(19) 0.029(2) 0.0068(19)
C21 0.089(3) 0.090(3) 0.069(2) -0.015(2) 0.037(2) 0.019(2)
C22 0.059(2) 0.095(3) 0.081(2) 0.002(2) 0.035(2) 0.012(2)
C23 0.090(3) 0.102(3) 0.079(3) -0.006(2) 0.026(2) 0.044(2)
O3 0.0423(12) 0.0800(15) 0.0492(12) -0.0125(11) 0.0094(11) 0.0096(11)
O4 0.0459(15) 0.129(2) 0.0581(15) -0.0269(15) -0.0037(13) 0.0161(14)
N3 0.0625(19) 0.085(2) 0.0656(18) -0.0230(16) 0.0223(16) 0.0145(16)
N4 0.0632(18) 0.0561(16) 0.0491(15) -0.0131(13) 0.0168(14) 0.0020(13)
C24 0.0428(18) 0.0499(18) 0.0430(17) -0.0031(14) 0.0100(15) -0.0006(14)
C25 0.0438(18) 0.0575(19) 0.0547(19) -0.0035(15) 0.0179(16) 0.0073(14)
C26 0.055(2) 0.0521(18) 0.0526(19) -0.0088(15) 0.0216(17) 0.0044(15)
C27 0.051(2) 0.063(2) 0.0469(18) -0.0094(15) 0.0104(16) 0.0075(16)
C28 0.0469(18) 0.0564(19) 0.0456(17) -0.0039(15) 0.0127(15) 0.0091(14)
C29 0.0418(17) 0.0437(16) 0.0396(16) -0.0018(13) 0.0134(14) 0.0018(13)
C30 0.0406(17) 0.0418(16) 0.0390(15) 0.0022(12) 0.0133(14) -0.0009(12)
C31 0.0396(17) 0.0493(17) 0.0387(16) -0.0024(13) 0.0110(14) -0.0026(13)
C32 0.0440(19) 0.074(2) 0.0484(19) -0.0118(17) 0.0115(17) -0.0005(16)
C33 0.0443(18) 0.0579(18) 0.0385(16) -0.0053(14) 0.0103(14) -0.0078(14)
C34 0.0454(18) 0.0488(17) 0.0428(16) -0.0040(13) 0.0193(15) -0.0056(14)
C35 0.0419(17) 0.0425(16) 0.0387(15) 0.0026(12) 0.0157(14) -0.0014(12)
C36 0.0425(17) 0.0454(16) 0.0350(15) 0.0014(13) 0.0123(13) 0.0009(13)
C37 0.053(2) 0.064(2) 0.0427(16) -0.0078(15) 0.0166(15) -0.0023(16)
C38 0.055(2) 0.0486(18) 0.0483(17) 0.0023(14) 0.0246(16) 0.0027(14)
C39 0.0469(17) 0.0441(16) 0.0400(15) 0.0067(13) 0.0188(15) 0.0015(13)
C40 0.0496(19) 0.0554(18) 0.0425(16) 0.0022(14) 0.0180(16) 0.0053(14)
C41 0.0475(19) 0.068(2) 0.0521(18) 0.0059(16) 0.0175(16) 0.0093(16)
C42 0.057(2) 0.069(2) 0.068(2) 0.0050(19) 0.025(2) 0.0176(18)
C43 0.068(2) 0.066(2) 0.064(2) -0.0113(18) 0.030(2) 0.0113(18)
C44 0.073(3) 0.087(3) 0.086(3) -0.014(2) 0.043(2) 0.014(2)
C45 0.096(3) 0.107(3) 0.063(2) -0.033(2) 0.018(2) 0.020(2)
C46 0.086(3) 0.082(3) 0.071(2) -0.034(2) 0.024(2) 0.006(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O1 C1 121.7(2)
C3 N1 C22 120.6(3)
C3 N1 C21 120.0(3)
C22 N1 C21 117.2(3)
C15 N2 C14 119.3(3)
C15 N2 C23 119.2(3)
C14 N2 C23 114.1(3)
C2 C1 C6 124.4(3)
C2 C1 O1 113.8(2)
C6 C1 O1 121.8(3)
C1 C2 C3 119.9(3)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
N1 C3 C2 121.1(3)
N1 C3 C4 122.0(3)
C2 C3 C4 116.8(3)
C5 C4 C3 121.6(3)
C5 C4 H4A 119.2
C3 C4 H4A 119.2
C4 C5 C6 122.0(3)
C4 C5 H5A 119.0
C6 C5 H5A 119.0
C1 C6 C5 115.2(3)
C1 C6 C7 119.4(3)
C5 C6 C7 125.4(2)
C13 C7 C8 118.0(3)
C13 C7 C6 124.5(3)
C8 C7 C6 117.5(2)
C10 C8 C7 120.3(3)
C10 C8 C9 118.5(3)
C7 C8 C9 121.2(3)
O2 C9 O1 116.4(3)
O2 C9 C8 125.3(3)
O1 C9 C8 118.3(3)
C11 C10 C8 121.4(3)
C11 C10 H10A 119.3
C8 C10 H10A 119.3
C10 C11 C12 119.7(3)
C10 C11 C14 120.2(3)
C12 C11 C14 120.1(3)
C13 C12 C11 118.8(3)
C13 C12 C16 123.3(3)
C11 C12 C16 117.9(3)
C12 C13 C7 121.9(3)
C12 C13 H13A 119.1
C7 C13 H13A 119.1
N2 C14 C11 113.8(3)
N2 C14 H14A 108.8
C11 C14 H14A 108.8
N2 C14 H14B 108.8
C11 C14 H14B 108.8
H14A C14 H14B 107.7
N2 C15 C20 121.3(3)
N2 C15 C16 119.7(3)
C20 C15 C16 118.9(3)
C17 C16 C15 118.2(3)
C17 C16 C12 122.2(3)
C15 C16 C12 119.6(3)
C18 C17 C16 122.1(3)
C18 C17 H17A 118.9
C16 C17 H17A 118.9
C17 C18 C19 119.2(3)
C17 C18 H18A 120.4
C19 C18 H18A 120.4
C20 C19 C18 120.6(3)
C20 C19 H19A 119.7
C18 C19 H19A 119.7
C19 C20 C15 120.9(3)
C19 C20 H20A 119.6
C15 C20 H20A 119.6
N1 C21 H21A 109.5
N1 C21 H21B 109.5
H21A C21 H21B 109.5
N1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 H22A 109.5
N1 C22 H22B 109.5
H22A C22 H22B 109.5
N1 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
N2 C23 H23A 109.5
N2 C23 H23B 109.5
H23A C23 H23B 109.5
N2 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C32 O3 C24 122.0(2)
C26 N3 C45 121.8(3)
C26 N3 C44 120.6(3)
C45 N3 C44 117.1(3)
C38 N4 C37 116.4(2)
C38 N4 C46 119.1(3)
C37 N4 C46 112.3(2)
C25 C24 C29 124.4(3)
C25 C24 O3 114.0(3)
C29 C24 O3 121.6(3)
C24 C25 C26 120.0(3)
C24 C25 H25A 120.0
C26 C25 H25A 120.0
N3 C26 C25 121.6(3)
N3 C26 C27 121.6(3)
C25 C26 C27 116.8(3)
C28 C27 C26 121.6(3)
C28 C27 H27A 119.2
C26 C27 H27A 119.2
C27 C28 C29 122.4(3)
C27 C28 H28A 118.8
C29 C28 H28A 118.8
C24 C29 C28 114.8(3)
C24 C29 C30 119.3(2)
C28 C29 C30 125.9(3)
C36 C30 C31 117.7(3)
C36 C30 C29 124.4(2)
C31 C30 C29 117.9(2)
C33 C31 C30 120.5(3)
C33 C31 C32 118.4(3)
C30 C31 C32 121.1(3)
O4 C32 O3 117.1(3)
O4 C32 C31 124.9(3)
O3 C32 C31 118.0(3)
C34 C33 C31 121.3(3)
C34 C33 H33A 119.4
C31 C33 H33A 119.4
C33 C34 C35 119.6(3)
C33 C34 C37 120.9(3)
C35 C34 C37 119.5(3)
C36 C35 C34 119.0(3)
C36 C35 C39 123.3(2)
C34 C35 C39 117.7(2)
C35 C36 C30 122.0(3)
C35 C36 H36A 119.0
C30 C36 H36A 119.0
N4 C37 C34 112.1(2)
N4 C37 H37A 109.2
C34 C37 H37A 109.2
N4 C37 H37B 109.2
C34 C37 H37B 109.2
H37A C37 H37B 107.9
C43 C38 N4 121.6(3)
C43 C38 C39 118.6(3)
N4 C38 C39 119.8(3)
C40 C39 C38 118.8(3)
C40 C39 C35 122.0(3)
C38 C39 C35 119.1(3)
C41 C40 C39 121.7(3)
C41 C40 H40A 119.1
C39 C40 H40A 119.1
C42 C41 C40 119.0(3)
C42 C41 H41A 120.5
C40 C41 H41A 120.5
C41 C42 C43 120.6(3)
C41 C42 H42A 119.7
C43 C42 H42A 119.7
C42 C43 C38 121.3(3)
C42 C43 H43A 119.4
C38 C43 H43A 119.4
N3 C44 H44A 109.5
N3 C44 H44B 109.5
H44A C44 H44B 109.5
N3 C44 H44C 109.5
H44A C44 H44C 109.5
H44B C44 H44C 109.5
N3 C45 H45A 109.5
N3 C45 H45B 109.5
H45A C45 H45B 109.5
N3 C45 H45C 109.5
H45A C45 H45C 109.5
H45B C45 H45C 109.5
N4 C46 H46A 109.5
N4 C46 H46B 109.5
H46A C46 H46B 109.5
N4 C46 H46C 109.5
H46A C46 H46C 109.5
H46B C46 H46C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.366(3)
O1 C1 1.392(3)
O2 C9 1.216(3)
N1 C3 1.377(4)
N1 C22 1.448(4)
N1 C21 1.453(4)
N2 C15 1.388(4)
N2 C14 1.432(4)
N2 C23 1.455(4)
C1 C2 1.370(4)
C1 C6 1.378(4)
C2 C3 1.399(4)
C2 H2A 0.9300
C3 C4 1.405(4)
C4 C5 1.367(4)
C4 H4A 0.9300
C5 C6 1.405(4)
C5 H5A 0.9300
C6 C7 1.459(4)
C7 C13 1.402(4)
C7 C8 1.407(4)
C8 C10 1.383(4)
C8 C9 1.452(4)
C10 C11 1.376(4)
C10 H10A 0.9300
C11 C12 1.411(4)
C11 C14 1.495(4)
C12 C13 1.390(4)
C12 C16 1.467(4)
C13 H13A 0.9300
C14 H14A 0.9700
C14 H14B 0.9700
C15 C20 1.397(4)
C15 C16 1.415(4)
C16 C17 1.391(4)
C17 C18 1.374(4)
C17 H17A 0.9300
C18 C19 1.377(5)
C18 H18A 0.9300
C19 C20 1.372(5)
C19 H19A 0.9300
C20 H20A 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
O3 C32 1.358(3)
O3 C24 1.396(3)
O4 C32 1.206(3)
N3 C26 1.377(4)
N3 C45 1.434(4)
N3 C44 1.444(4)
N4 C38 1.404(4)
N4 C37 1.443(4)
N4 C46 1.456(4)
C24 C25 1.373(4)
C24 C29 1.383(4)
C25 C26 1.396(4)
C25 H25A 0.9300
C26 C27 1.405(4)
C27 C28 1.367(4)
C27 H27A 0.9300
C28 C29 1.401(4)
C28 H28A 0.9300
C29 C30 1.450(4)
C30 C36 1.396(4)
C30 C31 1.409(4)
C31 C33 1.390(4)
C31 C32 1.459(4)
C33 C34 1.366(4)
C33 H33A 0.9300
C34 C35 1.415(4)
C34 C37 1.504(4)
C35 C36 1.389(4)
C35 C39 1.474(4)
C36 H36A 0.9300
C37 H37A 0.9700
C37 H37B 0.9700
C38 C43 1.392(4)
C38 C39 1.408(4)
C39 C40 1.389(4)
C40 C41 1.386(4)
C40 H40A 0.9300
C41 C42 1.369(4)
C41 H41A 0.9300
C42 C43 1.377(4)
C42 H42A 0.9300
C43 H43A 0.9300
C44 H44A 0.9600
C44 H44B 0.9600
C44 H44C 0.9600
C45 H45A 0.9600
C45 H45B 0.9600
C45 H45C 0.9600
C46 H46A 0.9600
C46 H46B 0.9600
C46 H46C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 O1 C1 C2 177.6(2)
C9 O1 C1 C6 -1.2(4)
C6 C1 C2 C3 2.0(5)
O1 C1 C2 C3 -176.8(2)
C22 N1 C3 C2 -161.2(3)
C21 N1 C3 C2 1.3(5)
C22 N1 C3 C4 20.7(5)
C21 N1 C3 C4 -176.8(3)
C1 C2 C3 N1 -178.9(3)
C1 C2 C3 C4 -0.7(4)
N1 C3 C4 C5 177.4(3)
C2 C3 C4 C5 -0.8(4)
C3 C4 C5 C6 1.1(5)
C2 C1 C6 C5 -1.7(4)
O1 C1 C6 C5 177.0(2)
C2 C1 C6 C7 179.3(3)
O1 C1 C6 C7 -2.0(4)
C4 C5 C6 C1 0.1(4)
C4 C5 C6 C7 179.0(3)
C1 C6 C7 C13 -177.6(3)
C5 C6 C7 C13 3.6(4)
C1 C6 C7 C8 3.1(4)
C5 C6 C7 C8 -175.8(3)
C13 C7 C8 C10 -0.3(4)
C6 C7 C8 C10 179.1(2)
C13 C7 C8 C9 179.4(2)
C6 C7 C8 C9 -1.2(4)
C1 O1 C9 O2 -177.6(3)
C1 O1 C9 C8 3.1(4)
C10 C8 C9 O2 -1.4(4)
C7 C8 C9 O2 179.0(3)
C10 C8 C9 O1 177.9(2)
C7 C8 C9 O1 -1.8(4)
C7 C8 C10 C11 0.2(4)
C9 C8 C10 C11 -179.5(3)
C8 C10 C11 C12 0.6(4)
C8 C10 C11 C14 179.7(3)
C10 C11 C12 C13 -1.2(4)
C14 C11 C12 C13 179.7(3)
C10 C11 C12 C16 179.1(3)
C14 C11 C12 C16 0.0(4)
C11 C12 C13 C7 1.1(4)
C16 C12 C13 C7 -179.3(3)
C8 C7 C13 C12 -0.4(4)
C6 C7 C13 C12 -179.7(3)
C15 N2 C14 C11 36.8(4)
C23 N2 C14 C11 -173.5(3)
C10 C11 C14 N2 157.6(3)
C12 C11 C14 N2 -23.3(4)
C14 N2 C15 C20 156.9(3)
C23 N2 C15 C20 8.7(5)
C14 N2 C15 C16 -26.5(5)
C23 N2 C15 C16 -174.7(3)
N2 C15 C16 C17 -177.1(3)
C20 C15 C16 C17 -0.4(4)
N2 C15 C16 C12 1.0(4)
C20 C15 C16 C12 177.7(3)
C13 C12 C16 C17 10.3(4)
C11 C12 C16 C17 -170.1(3)
C13 C12 C16 C15 -167.8(3)
C11 C12 C16 C15 11.8(4)
C15 C16 C17 C18 -0.3(5)
C12 C16 C17 C18 -178.3(3)
C16 C17 C18 C19 1.3(5)
C17 C18 C19 C20 -1.6(6)
C18 C19 C20 C15 0.9(6)
N2 C15 C20 C19 176.8(3)
C16 C15 C20 C19 0.2(5)
C32 O3 C24 C25 177.3(3)
C32 O3 C24 C29 -2.9(4)
C29 C24 C25 C26 0.3(5)
O3 C24 C25 C26 -180.0(3)
C45 N3 C26 C25 -171.0(3)
C44 N3 C26 C25 1.3(5)
C45 N3 C26 C27 8.2(5)
C44 N3 C26 C27 -179.6(3)
C24 C25 C26 N3 -180.0(3)
C24 C25 C26 C27 0.8(4)
N3 C26 C27 C28 179.8(3)
C25 C26 C27 C28 -1.0(5)
C26 C27 C28 C29 0.2(5)
C25 C24 C29 C28 -1.1(4)
O3 C24 C29 C28 179.1(3)
C25 C24 C29 C30 179.4(3)
O3 C24 C29 C30 -0.3(4)
C27 C28 C29 C24 0.9(4)
C27 C28 C29 C30 -179.7(3)
C24 C29 C30 C36 -177.7(3)
C28 C29 C30 C36 2.9(4)
C24 C29 C30 C31 2.4(4)
C28 C29 C30 C31 -177.0(3)
C36 C30 C31 C33 -0.1(4)
C29 C30 C31 C33 179.8(3)
C36 C30 C31 C32 178.6(3)
C29 C30 C31 C32 -1.5(4)
C24 O3 C32 O4 -176.7(3)
C24 O3 C32 C31 3.8(4)
C33 C31 C32 O4 -2.3(5)
C30 C31 C32 O4 179.0(3)
C33 C31 C32 O3 177.2(3)
C30 C31 C32 O3 -1.5(4)
C30 C31 C33 C34 0.3(4)
C32 C31 C33 C34 -178.5(3)
C31 C33 C34 C35 -0.7(4)
C31 C33 C34 C37 -178.4(3)
C33 C34 C35 C36 0.9(4)
C37 C34 C35 C36 178.7(2)
C33 C34 C35 C39 -178.3(3)
C37 C34 C35 C39 -0.6(4)
C34 C35 C36 C30 -0.8(4)
C39 C35 C36 C30 178.4(2)
C31 C30 C36 C35 0.4(4)
C29 C30 C36 C35 -179.5(2)
C38 N4 C37 C34 -45.9(4)
C46 N4 C37 C34 171.9(3)
C33 C34 C37 N4 -152.7(3)
C35 C34 C37 N4 29.5(4)
C37 N4 C38 C43 -149.4(3)
C46 N4 C38 C43 -9.8(4)
C37 N4 C38 C39 33.7(4)
C46 N4 C38 C39 173.3(3)
C43 C38 C39 C40 0.1(4)
N4 C38 C39 C40 177.1(3)
C43 C38 C39 C35 -179.5(3)
N4 C38 C39 C35 -2.5(4)
C36 C35 C39 C40 -12.7(4)
C34 C35 C39 C40 166.6(3)
C36 C35 C39 C38 166.9(3)
C34 C35 C39 C38 -13.9(4)
C38 C39 C40 C41 0.0(4)
C35 C39 C40 C41 179.6(3)
C39 C40 C41 C42 -0.5(5)
C40 C41 C42 C43 0.8(5)
C41 C42 C43 C38 -0.7(5)
N4 C38 C43 C42 -176.7(3)
C39 C38 C43 C42 0.2(5)
|
1502038.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502038.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502038
loop_
_publ_author_name
'Chen, Jiun-Jia'
'Li, Kuan-Ting'
'Yang, Ding-Yah'
_publ_section_title
;
Synthesis of coumarin/phenanthridine-fused heterocycles and their
photochemical and thermochromic properties.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1658
_journal_page_last 1661
_journal_paper_doi 10.1021/ol200117b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C24 H22 N2 O3'
_chemical_formula_sum 'C24 H22 N2 O3'
_chemical_formula_weight 386.44
_space_group_IT_number 61
_symmetry_cell_setting orthorhombic
_symmetry_Int_Tables_number 61
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 16
_cell_length_a 15.6502(11)
_cell_length_b 13.1606(10)
_cell_length_c 37.823(3)
_cell_measurement_temperature 297(2)
_cell_volume 7790.3(10)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0791
_diffrn_reflns_av_sigmaI/netI 0.0556
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 46
_diffrn_reflns_limit_l_min -39
_diffrn_reflns_number 42540
_diffrn_reflns_theta_full 26.05
_diffrn_reflns_theta_max 26.05
_diffrn_reflns_theta_min 2.09
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.088
_exptl_absorpt_correction_T_max 1.000000
_exptl_absorpt_correction_T_min 0.625959
_exptl_absorpt_correction_type empirical
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.318
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 3264
_exptl_crystal_size_max 0.57
_exptl_crystal_size_mid 0.34
_exptl_crystal_size_min 0.19
_refine_diff_density_max 0.368
_refine_diff_density_min -0.299
_refine_diff_density_rms 0.054
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 523
_refine_ls_number_reflns 7691
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.017
_refine_ls_R_factor_all 0.1569
_refine_ls_R_factor_gt 0.0718
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1168P)^2^+5.2205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1987
_refine_ls_wR_factor_ref 0.2572
_reflns_number_gt 3576
_reflns_number_total 7691
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200117b_si_003.cif
_cod_data_source_block jj010m
_cod_database_code 1502038
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.61807(16) 0.8752(2) 0.02294(7) 0.0621(8) Uani 1 1 d .
O2 O 0.72134(18) 0.7966(2) -0.00499(9) 0.0780(9) Uani 1 1 d .
O3 O 0.6262(2) 0.5280(3) -0.09855(10) 0.0944(11) Uani 1 1 d .
N1 N 0.4132(2) 1.0847(3) 0.07863(11) 0.0795(11) Uani 1 1 d .
N2 N 0.5281(3) 0.4115(3) -0.07381(10) 0.0721(10) Uani 1 1 d .
C1 C 0.5323(2) 0.8914(3) 0.02976(10) 0.0526(10) Uani 1 1 d .
C2 C 0.5154(3) 0.9751(3) 0.05045(11) 0.0589(11) Uani 1 1 d .
H2A H 0.5602 1.0144 0.0591 0.071 Uiso 1 1 calc R
C3 C 0.4314(3) 1.0010(3) 0.05836(11) 0.0585(10) Uani 1 1 d .
C4 C 0.3664(3) 0.9394(3) 0.04436(12) 0.0633(11) Uani 1 1 d .
H4A H 0.3096 0.9554 0.0489 0.076 Uiso 1 1 calc R
C5 C 0.3854(3) 0.8562(3) 0.02420(11) 0.0602(11) Uani 1 1 d .
H5A H 0.3408 0.8168 0.0154 0.072 Uiso 1 1 calc R
C6 C 0.4693(2) 0.8282(3) 0.01629(10) 0.0524(10) Uani 1 1 d .
C7 C 0.4950(2) 0.7403(3) -0.00440(9) 0.0501(9) Uani 1 1 d .
C8 C 0.4380(2) 0.6668(3) -0.01684(10) 0.0536(10) Uani 1 1 d .
H8A H 0.3801 0.6737 -0.0119 0.064 Uiso 1 1 calc R
C9 C 0.4657(3) 0.5834(3) -0.03655(10) 0.0537(10) Uani 1 1 d .
C10 C 0.4075(3) 0.5034(3) -0.04905(10) 0.0543(10) Uani 1 1 d .
C11 C 0.3200(3) 0.5041(3) -0.04151(11) 0.0623(11) Uani 1 1 d .
H11A H 0.2975 0.5577 -0.0285 0.075 Uiso 1 1 calc R
C12 C 0.2665(3) 0.4290(3) -0.05258(12) 0.0723(13) Uani 1 1 d .
H12A H 0.2087 0.4309 -0.0469 0.087 Uiso 1 1 calc R
C13 C 0.2993(3) 0.3499(4) -0.07235(13) 0.0771(13) Uani 1 1 d .
H13A H 0.2631 0.2990 -0.0805 0.093 Uiso 1 1 calc R
C14 C 0.3844(3) 0.3456(3) -0.08010(12) 0.0749(13) Uani 1 1 d .
H14A H 0.4054 0.2920 -0.0936 0.090 Uiso 1 1 calc R
C15 C 0.4408(3) 0.4209(3) -0.06795(10) 0.0597(11) Uani 1 1 d .
C16 C 0.5883(3) 0.4897(4) -0.06664(12) 0.0696(12) Uani 1 1 d .
H16A H 0.6345 0.4586 -0.0529 0.084 Uiso 1 1 calc R
C17 C 0.5527(3) 0.5746(3) -0.04443(10) 0.0574(10) Uani 1 1 d .
C18 C 0.6097(3) 0.6456(3) -0.03176(11) 0.0593(11) Uani 1 1 d .
H18A H 0.6676 0.6383 -0.0366 0.071 Uiso 1 1 calc R
C19 C 0.5822(2) 0.7277(3) -0.01193(10) 0.0544(10) Uani 1 1 d .
C20 C 0.6457(3) 0.7994(3) 0.00114(11) 0.0606(11) Uani 1 1 d .
C21 C 0.4821(3) 1.1437(4) 0.09410(14) 0.0880(15) Uani 1 1 d .
H21A H 0.5360 1.1167 0.0864 0.132 Uiso 1 1 calc R
H21B H 0.4786 1.1401 0.1194 0.132 Uiso 1 1 calc R
H21C H 0.4773 1.2132 0.0867 0.132 Uiso 1 1 calc R
C22 C 0.3266(3) 1.1128(4) 0.08681(14) 0.0857(15) Uani 1 1 d .
H22A H 0.2880 1.0677 0.0749 0.129 Uiso 1 1 calc R
H22B H 0.3164 1.1812 0.0791 0.129 Uiso 1 1 calc R
H22C H 0.3177 1.1082 0.1119 0.129 Uiso 1 1 calc R
C23 C 0.5617(4) 0.3249(3) -0.09332(15) 0.0943(17) Uani 1 1 d .
H23A H 0.5169 0.2761 -0.0970 0.141 Uiso 1 1 calc R
H23B H 0.6071 0.2941 -0.0801 0.141 Uiso 1 1 calc R
H23C H 0.5830 0.3473 -0.1158 0.141 Uiso 1 1 calc R
C24 C 0.5661(5) 0.5707(5) -0.12288(15) 0.116(2) Uani 1 1 d .
H24A H 0.5958 0.5946 -0.1435 0.174 Uiso 1 1 calc R
H24B H 0.5369 0.6264 -0.1118 0.174 Uiso 1 1 calc R
H24C H 0.5254 0.5197 -0.1296 0.174 Uiso 1 1 calc R
O4 O 0.56008(17) 0.6467(2) 0.21007(8) 0.0701(8) Uani 1 1 d .
O5 O 0.46820(18) 0.5614(2) 0.24223(9) 0.0809(10) Uani 1 1 d .
O6 O 0.6056(3) 0.3093(3) 0.33538(10) 0.0976(12) Uani 1 1 d .
N3 N 0.7389(3) 0.8762(3) 0.14841(12) 0.0985(14) Uani 1 1 d .
N4 N 0.7017(2) 0.1996(2) 0.30494(9) 0.0564(9) Uani 1 1 d .
C25 C 0.6428(2) 0.6719(3) 0.20038(11) 0.0570(10) Uani 1 1 d .
C26 C 0.6501(3) 0.7559(3) 0.17933(12) 0.0669(12) Uani 1 1 d .
H26A H 0.6012 0.7902 0.1721 0.080 Uiso 1 1 calc R
C27 C 0.7295(3) 0.7905(3) 0.16874(12) 0.0711(12) Uani 1 1 d .
C28 C 0.8007(3) 0.7350(4) 0.18035(12) 0.0743(13) Uani 1 1 d .
H28A H 0.8551 0.7558 0.1736 0.089 Uiso 1 1 calc R
C29 C 0.7921(3) 0.6513(3) 0.20126(12) 0.0651(11) Uani 1 1 d .
H29A H 0.8410 0.6174 0.2087 0.078 Uiso 1 1 calc R
C30 C 0.7122(2) 0.6147(3) 0.21187(10) 0.0516(9) Uani 1 1 d .
C31 C 0.6969(2) 0.5261(3) 0.23402(10) 0.0481(9) Uani 1 1 d .
C32 C 0.7616(2) 0.4617(3) 0.24632(10) 0.0493(9) Uani 1 1 d .
H32A H 0.8177 0.4740 0.2395 0.059 Uiso 1 1 calc R
C33 C 0.7443(2) 0.3795(3) 0.26856(9) 0.0456(9) Uani 1 1 d .
C34 C 0.8114(2) 0.3133(3) 0.28261(10) 0.0482(9) Uani 1 1 d .
C35 C 0.8970(3) 0.3343(3) 0.27862(11) 0.0632(11) Uani 1 1 d .
H35A H 0.9129 0.3933 0.2668 0.076 Uiso 1 1 calc R
C36 C 0.9602(3) 0.2709(4) 0.29161(12) 0.0765(13) Uani 1 1 d .
H36A H 1.0177 0.2867 0.2885 0.092 Uiso 1 1 calc R
C37 C 0.9363(3) 0.1847(4) 0.30903(12) 0.0787(14) Uani 1 1 d .
H37A H 0.9782 0.1413 0.3177 0.094 Uiso 1 1 calc R
C38 C 0.8518(3) 0.1608(3) 0.31399(11) 0.0683(12) Uani 1 1 d .
H38A H 0.8376 0.1019 0.3262 0.082 Uiso 1 1 calc R
C39 C 0.7865(3) 0.2235(3) 0.30096(10) 0.0527(10) Uani 1 1 d .
C40 C 0.6355(3) 0.2734(3) 0.30197(11) 0.0616(11) Uani 1 1 d .
H40A H 0.5870 0.2389 0.2908 0.074 Uiso 1 1 calc R
C41 C 0.6594(2) 0.3592(3) 0.27792(10) 0.0502(9) Uani 1 1 d .
C42 C 0.5948(2) 0.4225(3) 0.26564(11) 0.0549(10) Uani 1 1 d .
H42A H 0.5385 0.4092 0.2720 0.066 Uiso 1 1 calc R
C43 C 0.6125(2) 0.5048(3) 0.24418(10) 0.0502(9) Uani 1 1 d .
C44 C 0.5421(3) 0.5696(3) 0.23306(12) 0.0629(11) Uani 1 1 d .
C45 C 0.6654(4) 0.9321(4) 0.13648(17) 0.119(2) Uani 1 1 d .
H45A H 0.6144 0.8990 0.1446 0.178 Uiso 1 1 calc R
H45B H 0.6652 0.9346 0.1111 0.178 Uiso 1 1 calc R
H45C H 0.6675 0.9999 0.1458 0.178 Uiso 1 1 calc R
C46 C 0.8226(4) 0.9137(5) 0.13892(16) 0.116(2) Uani 1 1 d .
H46A H 0.8656 0.8695 0.1485 0.174 Uiso 1 1 calc R
H46B H 0.8302 0.9809 0.1483 0.174 Uiso 1 1 calc R
H46C H 0.8279 0.9156 0.1136 0.174 Uiso 1 1 calc R
C47 C 0.6762(3) 0.1056(3) 0.32230(11) 0.0706(12) Uani 1 1 d .
H47A H 0.7241 0.0601 0.3233 0.106 Uiso 1 1 calc R
H47B H 0.6307 0.0745 0.3092 0.106 Uiso 1 1 calc R
H47C H 0.6571 0.1203 0.3459 0.106 Uiso 1 1 calc R
C48 C 0.6653(5) 0.3597(5) 0.35577(16) 0.129(3) Uani 1 1 d .
H48A H 0.6395 0.3808 0.3776 0.194 Uiso 1 1 calc R
H48B H 0.6856 0.4183 0.3432 0.194 Uiso 1 1 calc R
H48C H 0.7124 0.3151 0.3607 0.194 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0446(16) 0.0651(18) 0.0767(19) -0.0094(15) -0.0011(13) -0.0040(13)
O2 0.0432(18) 0.084(2) 0.107(2) -0.0202(18) 0.0035(16) -0.0004(15)
O3 0.098(3) 0.085(2) 0.100(3) -0.020(2) 0.035(2) -0.003(2)
N1 0.065(2) 0.063(2) 0.110(3) -0.028(2) 0.005(2) 0.001(2)
N2 0.083(3) 0.058(2) 0.076(3) -0.0119(19) 0.023(2) 0.003(2)
C1 0.042(2) 0.058(2) 0.058(2) 0.003(2) -0.0034(17) -0.0008(18)
C2 0.057(3) 0.059(3) 0.061(3) -0.002(2) -0.004(2) -0.007(2)
C3 0.060(3) 0.052(2) 0.063(3) -0.005(2) 0.003(2) -0.001(2)
C4 0.048(2) 0.064(3) 0.078(3) -0.013(2) 0.004(2) 0.002(2)
C5 0.050(2) 0.061(3) 0.070(3) -0.010(2) 0.002(2) -0.001(2)
C6 0.047(2) 0.056(2) 0.054(2) -0.0027(19) -0.0007(18) 0.0002(19)
C7 0.046(2) 0.059(2) 0.046(2) -0.0003(18) 0.0021(16) 0.0006(19)
C8 0.048(2) 0.061(3) 0.051(2) -0.006(2) 0.0059(18) 0.0018(19)
C9 0.058(2) 0.057(2) 0.047(2) -0.0004(19) 0.0037(18) 0.000(2)
C10 0.063(3) 0.051(2) 0.049(2) -0.0023(19) 0.0014(18) 0.004(2)
C11 0.059(3) 0.060(3) 0.068(3) -0.008(2) -0.006(2) 0.000(2)
C12 0.066(3) 0.069(3) 0.082(3) -0.010(3) -0.005(2) -0.004(2)
C13 0.083(4) 0.063(3) 0.085(3) -0.006(3) -0.006(3) -0.011(3)
C14 0.096(4) 0.058(3) 0.071(3) -0.009(2) 0.003(3) -0.002(3)
C15 0.068(3) 0.059(3) 0.051(2) 0.001(2) 0.006(2) 0.005(2)
C16 0.071(3) 0.072(3) 0.065(3) -0.006(2) 0.008(2) 0.011(2)
C17 0.052(2) 0.064(3) 0.056(2) -0.005(2) 0.0061(19) 0.008(2)
C18 0.045(2) 0.067(3) 0.066(3) -0.006(2) 0.0036(19) 0.006(2)
C19 0.046(2) 0.063(3) 0.055(2) -0.002(2) -0.0006(18) 0.0016(19)
C20 0.052(3) 0.065(3) 0.065(3) -0.001(2) 0.001(2) 0.001(2)
C21 0.097(4) 0.068(3) 0.099(4) -0.025(3) -0.001(3) -0.008(3)
C22 0.083(4) 0.073(3) 0.101(4) -0.022(3) 0.022(3) 0.009(3)
C23 0.109(4) 0.054(3) 0.120(4) -0.016(3) 0.045(3) 0.007(3)
C24 0.172(7) 0.091(4) 0.085(4) 0.006(3) 0.015(4) 0.044(4)
O4 0.0481(17) 0.0646(18) 0.098(2) 0.0179(17) -0.0056(15) 0.0049(14)
O5 0.0400(17) 0.076(2) 0.127(3) 0.0116(19) -0.0020(17) -0.0007(15)
O6 0.133(3) 0.069(2) 0.091(3) 0.007(2) 0.038(2) -0.005(2)
N3 0.107(4) 0.079(3) 0.109(3) 0.046(3) -0.011(3) -0.010(3)
N4 0.065(2) 0.0379(17) 0.066(2) 0.0066(15) 0.0011(17) -0.0040(16)
C25 0.048(2) 0.055(2) 0.068(3) 0.003(2) -0.004(2) 0.0035(19)
C26 0.067(3) 0.054(3) 0.079(3) 0.013(2) -0.015(2) 0.004(2)
C27 0.086(3) 0.059(3) 0.068(3) 0.018(2) -0.008(2) -0.002(2)
C28 0.066(3) 0.071(3) 0.086(3) 0.027(3) -0.004(2) -0.012(2)
C29 0.051(3) 0.069(3) 0.075(3) 0.014(2) -0.005(2) -0.002(2)
C30 0.045(2) 0.049(2) 0.060(2) 0.0058(19) -0.0050(18) -0.0030(18)
C31 0.043(2) 0.044(2) 0.057(2) 0.0001(18) -0.0065(17) -0.0024(17)
C32 0.042(2) 0.049(2) 0.056(2) 0.0045(19) -0.0010(17) -0.0011(17)
C33 0.044(2) 0.043(2) 0.050(2) -0.0011(17) -0.0043(16) -0.0013(17)
C34 0.046(2) 0.046(2) 0.053(2) 0.0003(18) 0.0010(17) 0.0037(17)
C35 0.049(3) 0.062(3) 0.078(3) 0.016(2) -0.002(2) 0.006(2)
C36 0.055(3) 0.091(4) 0.084(3) 0.017(3) -0.002(2) 0.019(3)
C37 0.076(3) 0.089(4) 0.072(3) 0.017(3) -0.002(2) 0.032(3)
C38 0.090(4) 0.053(3) 0.062(3) 0.011(2) 0.008(2) 0.018(2)
C39 0.065(3) 0.045(2) 0.049(2) -0.0004(18) -0.0012(19) 0.0042(19)
C40 0.065(3) 0.048(2) 0.071(3) -0.002(2) 0.006(2) -0.014(2)
C41 0.046(2) 0.044(2) 0.061(2) 0.0028(18) -0.0023(18) -0.0101(17)
C42 0.039(2) 0.051(2) 0.074(3) 0.002(2) 0.0004(18) -0.0039(18)
C43 0.037(2) 0.046(2) 0.067(3) -0.0006(19) -0.0054(17) -0.0003(17)
C44 0.047(3) 0.057(3) 0.085(3) 0.006(2) -0.007(2) 0.001(2)
C45 0.133(5) 0.083(4) 0.140(5) 0.049(4) -0.029(4) 0.004(4)
C46 0.129(5) 0.104(5) 0.115(5) 0.053(4) 0.005(4) -0.030(4)
C47 0.101(4) 0.043(2) 0.068(3) 0.006(2) 0.005(2) -0.014(2)
C48 0.221(8) 0.077(4) 0.089(4) -0.004(3) 0.030(5) -0.049(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 O1 C1 122.2(3)
C24 O3 C16 114.0(4)
C3 N1 C22 121.5(4)
C3 N1 C21 120.0(4)
C22 N1 C21 118.4(4)
C15 N2 C16 123.8(4)
C15 N2 C23 120.3(4)
C16 N2 C23 115.2(4)
C2 C1 O1 114.5(3)
C2 C1 C6 123.6(4)
O1 C1 C6 121.9(4)
C1 C2 C3 119.9(4)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
N1 C3 C2 120.8(4)
N1 C3 C4 121.6(4)
C2 C3 C4 117.5(4)
C5 C4 C3 121.0(4)
C5 C4 H4A 119.5
C3 C4 H4A 119.5
C4 C5 C6 122.3(4)
C4 C5 H5A 118.8
C6 C5 H5A 118.8
C1 C6 C5 115.6(4)
C1 C6 C7 118.7(3)
C5 C6 C7 125.7(4)
C8 C7 C19 118.1(4)
C8 C7 C6 123.8(3)
C19 C7 C6 118.1(3)
C9 C8 C7 121.7(4)
C9 C8 H8A 119.2
C7 C8 H8A 119.2
C8 C9 C17 118.8(4)
C8 C9 C10 122.8(4)
C17 C9 C10 118.4(4)
C11 C10 C15 118.3(4)
C11 C10 C9 122.5(4)
C15 C10 C9 119.2(4)
C12 C11 C10 122.4(4)
C12 C11 H11A 118.8
C10 C11 H11A 118.8
C11 C12 C13 119.0(5)
C11 C12 H12A 120.5
C13 C12 H12A 120.5
C14 C13 C12 120.7(5)
C14 C13 H13A 119.6
C12 C13 H13A 119.6
C13 C14 C15 120.9(4)
C13 C14 H14A 119.5
C15 C14 H14A 119.5
N2 C15 C10 121.1(4)
N2 C15 C14 120.2(4)
C10 C15 C14 118.7(4)
N2 C16 O3 111.6(4)
N2 C16 C17 113.5(4)
O3 C16 C17 111.2(4)
N2 C16 H16A 106.7
O3 C16 H16A 106.7
C17 C16 H16A 106.7
C18 C17 C9 120.0(4)
C18 C17 C16 117.3(4)
C9 C17 C16 122.7(4)
C17 C18 C19 121.1(4)
C17 C18 H18A 119.5
C19 C18 H18A 119.5
C18 C19 C7 120.3(4)
C18 C19 C20 118.5(4)
C7 C19 C20 121.2(4)
O2 C20 O1 116.8(4)
O2 C20 C19 125.7(4)
O1 C20 C19 117.5(4)
N1 C21 H21A 109.5
N1 C21 H21B 109.5
H21A C21 H21B 109.5
N1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
N1 C22 H22A 109.5
N1 C22 H22B 109.5
H22A C22 H22B 109.5
N1 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
N2 C23 H23A 109.5
N2 C23 H23B 109.5
H23A C23 H23B 109.5
N2 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O3 C24 H24A 109.5
O3 C24 H24B 109.5
H24A C24 H24B 109.5
O3 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C44 O4 C25 122.5(3)
C48 O6 C40 115.5(4)
C27 N3 C45 120.7(5)
C27 N3 C46 121.1(5)
C45 N3 C46 118.2(4)
C39 N4 C40 122.5(3)
C39 N4 C47 120.6(3)
C40 N4 C47 114.6(3)
C26 C25 O4 115.2(4)
C26 C25 C30 123.6(4)
O4 C25 C30 121.2(4)
C25 C26 C27 120.7(4)
C25 C26 H26A 119.7
C27 C26 H26A 119.7
N3 C27 C26 122.0(4)
N3 C27 C28 121.2(5)
C26 C27 C28 116.8(4)
C29 C28 C27 121.6(4)
C29 C28 H28A 119.2
C27 C28 H28A 119.2
C28 C29 C30 122.2(4)
C28 C29 H29A 118.9
C30 C29 H29A 118.9
C25 C30 C29 115.0(4)
C25 C30 C31 119.0(3)
C29 C30 C31 126.0(4)
C32 C31 C43 117.9(3)
C32 C31 C30 123.9(3)
C43 C31 C30 118.2(3)
C33 C32 C31 122.0(3)
C33 C32 H32A 119.0
C31 C32 H32A 119.0
C32 C33 C41 118.9(3)
C32 C33 C34 122.7(3)
C41 C33 C34 118.4(3)
C35 C34 C39 119.1(4)
C35 C34 C33 122.6(3)
C39 C34 C33 118.3(3)
C34 C35 C36 122.4(4)
C34 C35 H35A 118.8
C36 C35 H35A 118.8
C37 C36 C35 118.4(4)
C37 C36 H36A 120.8
C35 C36 H36A 120.8
C36 C37 C38 121.4(4)
C36 C37 H37A 119.3
C38 C37 H37A 119.3
C37 C38 C39 121.3(4)
C37 C38 H38A 119.4
C39 C38 H38A 119.4
N4 C39 C38 122.1(4)
N4 C39 C34 120.5(3)
C38 C39 C34 117.4(4)
N4 C40 O6 113.2(4)
N4 C40 C41 112.4(3)
O6 C40 C41 111.7(3)
N4 C40 H40A 106.3
O6 C40 H40A 106.3
C41 C40 H40A 106.3
C42 C41 C33 119.4(3)
C42 C41 C40 118.3(3)
C33 C41 C40 122.3(3)
C43 C42 C41 121.3(3)
C43 C42 H42A 119.3
C41 C42 H42A 119.3
C42 C43 C31 120.4(3)
C42 C43 C44 118.5(3)
C31 C43 C44 121.1(4)
O5 C44 O4 116.4(4)
O5 C44 C43 126.0(4)
O4 C44 C43 117.6(4)
N3 C45 H45A 109.5
N3 C45 H45B 109.5
H45A C45 H45B 109.5
N3 C45 H45C 109.5
H45A C45 H45C 109.5
H45B C45 H45C 109.5
N3 C46 H46A 109.5
N3 C46 H46B 109.5
H46A C46 H46B 109.5
N3 C46 H46C 109.5
H46A C46 H46C 109.5
H46B C46 H46C 109.5
N4 C47 H47A 109.5
N4 C47 H47B 109.5
H47A C47 H47B 109.5
N4 C47 H47C 109.5
H47A C47 H47C 109.5
H47B C47 H47C 109.5
O6 C48 H48A 109.5
O6 C48 H48B 109.5
H48A C48 H48B 109.5
O6 C48 H48C 109.5
H48A C48 H48C 109.5
H48B C48 H48C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C20 1.365(5)
O1 C1 1.384(4)
O2 C20 1.206(5)
O3 C24 1.431(7)
O3 C16 1.436(5)
N1 C3 1.372(5)
N1 C22 1.438(6)
N1 C21 1.452(6)
N2 C15 1.389(5)
N2 C16 1.421(6)
N2 C23 1.457(5)
C1 C2 1.377(5)
C1 C6 1.386(5)
C2 C3 1.391(6)
C2 H2A 0.9300
C3 C4 1.404(6)
C4 C5 1.367(6)
C4 H4A 0.9300
C5 C6 1.397(5)
C5 H5A 0.9300
C6 C7 1.454(5)
C7 C8 1.397(5)
C7 C19 1.404(5)
C8 C9 1.396(5)
C8 H8A 0.9300
C9 C17 1.399(5)
C9 C10 1.470(5)
C10 C11 1.399(6)
C10 C15 1.401(5)
C11 C12 1.362(6)
C11 H11A 0.9300
C12 C13 1.381(6)
C12 H12A 0.9300
C13 C14 1.365(7)
C13 H13A 0.9300
C14 C15 1.405(6)
C14 H14A 0.9300
C16 C17 1.505(6)
C16 H16A 0.9800
C17 C18 1.377(6)
C18 C19 1.384(5)
C18 H18A 0.9300
C19 C20 1.458(6)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
O4 C44 1.366(5)
O4 C25 1.386(5)
O5 C44 1.212(5)
O6 C48 1.382(7)
O6 C40 1.428(5)
N3 C27 1.373(6)
N3 C45 1.438(7)
N3 C46 1.446(7)
N4 C39 1.373(5)
N4 C40 1.425(5)
N4 C47 1.455(5)
C25 C26 1.368(6)
C25 C30 1.391(5)
C26 C27 1.382(6)
C26 H26A 0.9300
C27 C28 1.404(6)
C28 C29 1.362(6)
C28 H28A 0.9300
C29 C30 1.399(5)
C29 H29A 0.9300
C30 C31 1.456(5)
C31 C32 1.399(5)
C31 C43 1.404(5)
C32 C33 1.396(5)
C32 H32A 0.9300
C33 C41 1.402(5)
C33 C34 1.464(5)
C34 C35 1.375(5)
C34 C39 1.425(5)
C35 C36 1.385(6)
C35 H35A 0.9300
C36 C37 1.364(7)
C36 H36A 0.9300
C37 C38 1.372(7)
C37 H37A 0.9300
C38 C39 1.403(6)
C38 H38A 0.9300
C40 C41 1.497(5)
C40 H40A 0.9800
C41 C42 1.390(5)
C42 C43 1.382(5)
C42 H42A 0.9300
C43 C44 1.455(5)
C45 H45A 0.9600
C45 H45B 0.9600
C45 H45C 0.9600
C46 H46A 0.9600
C46 H46B 0.9600
C46 H46C 0.9600
C47 H47A 0.9600
C47 H47B 0.9600
C47 H47C 0.9600
C48 H48A 0.9600
C48 H48B 0.9600
C48 H48C 0.9600
|
1502039.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502039.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502039
loop_
_publ_author_name
'Chen, Jiun-Jia'
'Li, Kuan-Ting'
'Yang, Ding-Yah'
_publ_section_title
;
Synthesis of coumarin/phenanthridine-fused heterocycles and their
photochemical and thermochromic properties.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1658
_journal_page_last 1661
_journal_paper_doi 10.1021/ol200117b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C25 H22 N2 O3'
_chemical_formula_sum 'C25 H22 N2 O3'
_chemical_formula_weight 398.45
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 14
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 101.217(2)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 11.5671(11)
_cell_length_b 8.6420(8)
_cell_length_c 21.537(2)
_cell_measurement_reflns_used 3385
_cell_measurement_temperature 297(2)
_cell_measurement_theta_max 25.113
_cell_measurement_theta_min 2.367
_cell_volume 2111.8(3)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0383
_diffrn_reflns_av_sigmaI/netI 0.0378
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 11577
_diffrn_reflns_theta_full 26.01
_diffrn_reflns_theta_max 26.01
_diffrn_reflns_theta_min 1.79
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_T_max 1.000000
_exptl_absorpt_correction_T_min 0.773149
_exptl_absorpt_correction_type empirical
_exptl_crystal_colour green
_exptl_crystal_density_diffrn 1.253
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 840
_exptl_crystal_size_max 0.62
_exptl_crystal_size_mid 0.38
_exptl_crystal_size_min 0.25
_platon_squeeze_details ' '
_refine_diff_density_max 0.208
_refine_diff_density_min -0.218
_refine_diff_density_rms 0.052
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.998
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 274
_refine_ls_number_reflns 4132
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 0.998
_refine_ls_R_factor_all 0.0880
_refine_ls_R_factor_gt 0.0611
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1183P)^2^+0.7830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1944
_refine_ls_wR_factor_ref 0.2151
_reflns_number_gt 2569
_reflns_number_total 4132
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200117b_si_004.cif
_cod_data_source_block jj026m
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1502039
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.86320(16) 0.2344(2) 0.02435(9) 0.0543(5) Uani 1 1 d .
O2 O 0.83983(19) 0.3503(3) 0.11195(11) 0.0738(7) Uani 1 1 d .
O3 O 1.26685(17) 0.4887(2) 0.25681(8) 0.0543(5) Uani 1 1 d .
N1 N 0.8754(2) -0.0272(3) -0.16812(12) 0.0688(8) Uani 1 1 d .
N2 N 1.3340(2) 0.7025(3) 0.20355(11) 0.0530(6) Uani 1 1 d .
C1 C 0.9294(2) 0.2009(3) -0.02119(12) 0.0439(6) Uani 1 1 d .
C2 C 0.8734(2) 0.1085(3) -0.06978(13) 0.0516(7) Uani 1 1 d .
H2A H 0.7972 0.0737 -0.0700 0.062 Uiso 1 1 calc R
C3 C 0.9303(2) 0.0665(3) -0.11906(13) 0.0507(7) Uani 1 1 d .
C4 C 1.0448(3) 0.1262(3) -0.11707(13) 0.0547(7) Uani 1 1 d .
H4A H 1.0845 0.1033 -0.1495 0.066 Uiso 1 1 calc R
C5 C 1.0976(2) 0.2178(3) -0.06752(13) 0.0493(7) Uani 1 1 d .
H5A H 1.1731 0.2550 -0.0674 0.059 Uiso 1 1 calc R
C6 C 1.0433(2) 0.2576(3) -0.01743(12) 0.0420(6) Uani 1 1 d .
C7 C 1.0953(2) 0.3516(3) 0.03738(11) 0.0393(6) Uani 1 1 d .
C8 C 1.0266(2) 0.3823(3) 0.08298(12) 0.0424(6) Uani 1 1 d .
C9 C 0.9054(2) 0.3253(3) 0.07564(12) 0.0486(7) Uani 1 1 d .
C10 C 1.0723(2) 0.4681(3) 0.13673(12) 0.0460(6) Uani 1 1 d .
H10A H 1.0247 0.4894 0.1659 0.055 Uiso 1 1 calc R
C11 C 1.1872(2) 0.5228(3) 0.14789(12) 0.0442(6) Uani 1 1 d .
C12 C 1.2589(2) 0.4917(3) 0.10287(12) 0.0419(6) Uani 1 1 d .
C13 C 1.2107(2) 0.4096(3) 0.04822(12) 0.0432(6) Uani 1 1 d .
H13A H 1.2566 0.3927 0.0179 0.052 Uiso 1 1 calc R
C14 C 1.3813(2) 0.5469(3) 0.11689(13) 0.0468(6) Uani 1 1 d .
C15 C 1.4651(2) 0.4975(3) 0.08311(14) 0.0543(7) Uani 1 1 d .
H15A H 1.4422 0.4290 0.0497 0.065 Uiso 1 1 calc R
C16 C 1.5813(3) 0.5461(4) 0.09710(15) 0.0628(8) Uani 1 1 d .
H16A H 1.6354 0.5115 0.0734 0.075 Uiso 1 1 calc R
C17 C 1.6148(3) 0.6466(4) 0.14680(16) 0.0658(9) Uani 1 1 d .
H17A H 1.6925 0.6805 0.1566 0.079 Uiso 1 1 calc R
C18 C 1.5363(3) 0.6976(4) 0.18211(15) 0.0602(8) Uani 1 1 d .
H18A H 1.5617 0.7659 0.2153 0.072 Uiso 1 1 calc R
C19 C 1.4169(2) 0.6490(3) 0.16925(13) 0.0513(7) Uani 1 1 d .
C20 C 1.2362(2) 0.6046(3) 0.20764(12) 0.0480(7) Uani 1 1 d .
H20A H 1.1737 0.6696 0.2186 0.058 Uiso 1 1 calc R
C21 C 1.3047(3) 0.5597(4) 0.31740(14) 0.0635(8) Uani 1 1 d .
H21A H 1.3270 0.4799 0.3492 0.076 Uiso 1 1 calc R
H21B H 1.2399 0.6179 0.3284 0.076 Uiso 1 1 calc R
C22 C 1.4078(3) 0.6663(4) 0.31753(14) 0.0649(8) Uani 1 1 d .
H22A H 1.4759 0.6072 0.3111 0.078 Uiso 1 1 calc R
H22B H 1.4279 0.7192 0.3579 0.078 Uiso 1 1 calc R
C23 C 1.3738(3) 0.7839(4) 0.26428(14) 0.0662(9) Uani 1 1 d .
H23A H 1.3110 0.8498 0.2731 0.079 Uiso 1 1 calc R
H23B H 1.4411 0.8488 0.2616 0.079 Uiso 1 1 calc R
C24 C 0.7606(3) -0.0917(4) -0.16655(16) 0.0675(9) Uani 1 1 d .
H24A H 0.7354 -0.1551 -0.2033 0.116(15) Uiso 1 1 calc R
H24B H 0.7051 -0.0094 -0.1662 0.16(2) Uiso 1 1 calc R
H24C H 0.7652 -0.1536 -0.1291 0.125(16) Uiso 1 1 calc R
C25 C 0.9317(3) -0.0717(5) -0.21872(17) 0.0855(11) Uani 1 1 d .
H25A H 1.0064 -0.0202 -0.2142 0.128 Uiso 1 1 calc R
H25B H 0.8829 -0.0433 -0.2584 0.128 Uiso 1 1 calc R
H25C H 0.9438 -0.1817 -0.2176 0.128 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0447(11) 0.0617(13) 0.0581(11) -0.0038(9) 0.0140(9) -0.0090(9)
O2 0.0576(13) 0.0930(18) 0.0775(14) -0.0153(13) 0.0300(11) -0.0116(12)
O3 0.0681(13) 0.0417(11) 0.0500(10) -0.0015(8) 0.0039(9) 0.0017(9)
N1 0.0690(17) 0.0704(18) 0.0643(16) -0.0147(13) 0.0062(13) -0.0146(14)
N2 0.0608(15) 0.0359(12) 0.0576(13) -0.0026(10) -0.0002(11) -0.0008(11)
C1 0.0446(14) 0.0397(13) 0.0470(14) 0.0036(11) 0.0082(11) 0.0014(11)
C2 0.0461(15) 0.0470(15) 0.0589(16) 0.0034(13) 0.0031(13) -0.0075(12)
C3 0.0528(16) 0.0432(15) 0.0529(15) 0.0002(12) 0.0024(13) -0.0006(12)
C4 0.0535(17) 0.0568(17) 0.0546(16) -0.0026(14) 0.0125(13) 0.0012(14)
C5 0.0428(14) 0.0508(16) 0.0547(15) -0.0026(12) 0.0108(12) -0.0036(12)
C6 0.0396(14) 0.0365(13) 0.0484(14) 0.0055(11) 0.0050(11) 0.0018(11)
C7 0.0390(13) 0.0345(12) 0.0436(13) 0.0060(10) 0.0060(10) 0.0036(10)
C8 0.0385(13) 0.0410(14) 0.0471(14) 0.0075(11) 0.0073(11) 0.0050(11)
C9 0.0458(15) 0.0526(16) 0.0483(14) 0.0026(12) 0.0119(12) -0.0008(13)
C10 0.0467(15) 0.0455(15) 0.0471(14) 0.0018(12) 0.0128(11) 0.0067(12)
C11 0.0468(15) 0.0363(13) 0.0482(14) 0.0043(11) 0.0063(11) 0.0065(11)
C12 0.0398(14) 0.0334(12) 0.0506(14) 0.0060(11) 0.0040(11) 0.0023(11)
C13 0.0418(14) 0.0411(14) 0.0484(14) 0.0034(11) 0.0132(11) 0.0018(11)
C14 0.0458(15) 0.0373(14) 0.0554(15) 0.0074(12) 0.0049(12) -0.0032(11)
C15 0.0486(16) 0.0533(17) 0.0597(16) 0.0046(13) 0.0075(13) -0.0056(13)
C16 0.0443(16) 0.070(2) 0.073(2) 0.0158(17) 0.0105(14) -0.0030(15)
C17 0.0474(17) 0.070(2) 0.074(2) 0.0190(17) -0.0048(15) -0.0155(16)
C18 0.0579(18) 0.0518(17) 0.0646(18) 0.0075(14) -0.0034(15) -0.0122(14)
C19 0.0564(17) 0.0377(14) 0.0558(16) 0.0088(12) 0.0006(13) -0.0043(13)
C20 0.0506(15) 0.0379(14) 0.0534(15) -0.0003(11) 0.0045(12) 0.0067(12)
C21 0.078(2) 0.0580(18) 0.0498(16) -0.0041(14) 0.0001(14) 0.0073(16)
C22 0.076(2) 0.0565(18) 0.0546(17) -0.0090(14) -0.0050(15) 0.0018(16)
C23 0.077(2) 0.0460(16) 0.070(2) -0.0114(14) 0.0016(17) -0.0054(15)
C24 0.072(2) 0.0550(19) 0.067(2) 0.0015(16) -0.0086(16) -0.0105(17)
C25 0.088(3) 0.098(3) 0.068(2) -0.027(2) 0.0086(19) -0.007(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O1 C1 122.1(2)
C21 O3 C20 111.0(2)
C3 N1 C25 122.1(3)
C3 N1 C24 119.7(3)
C25 N1 C24 118.1(3)
C19 N2 C20 118.0(2)
C19 N2 C23 119.9(2)
C20 N2 C23 109.9(2)
C2 C1 O1 114.6(2)
C2 C1 C6 123.3(2)
O1 C1 C6 122.1(2)
C1 C2 C3 120.4(3)
C1 C2 H2A 119.8
C3 C2 H2A 119.8
N1 C3 C2 121.1(3)
N1 C3 C4 121.7(3)
C2 C3 C4 117.2(2)
C5 C4 C3 120.5(3)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 123.0(3)
C4 C5 H5A 118.5
C6 C5 H5A 118.5
C1 C6 C5 115.6(2)
C1 C6 C7 118.5(2)
C5 C6 C7 125.9(2)
C13 C7 C8 117.8(2)
C13 C7 C6 124.1(2)
C8 C7 C6 118.0(2)
C10 C8 C7 120.5(2)
C10 C8 C9 118.1(2)
C7 C8 C9 121.4(2)
O2 C9 O1 117.0(2)
O2 C9 C8 125.3(3)
O1 C9 C8 117.7(2)
C11 C10 C8 121.5(2)
C11 C10 H10A 119.2
C8 C10 H10A 119.2
C10 C11 C12 119.0(2)
C10 C11 C20 120.3(2)
C12 C11 C20 120.6(2)
C13 C12 C11 118.8(2)
C13 C12 C14 123.4(2)
C11 C12 C14 117.8(2)
C12 C13 C7 122.3(2)
C12 C13 H13A 118.9
C7 C13 H13A 118.9
C15 C14 C19 118.7(3)
C15 C14 C12 122.4(2)
C19 C14 C12 118.8(2)
C16 C15 C14 122.7(3)
C16 C15 H15A 118.6
C14 C15 H15A 118.6
C17 C16 C15 118.4(3)
C17 C16 H16A 120.8
C15 C16 H16A 120.8
C18 C17 C16 121.4(3)
C18 C17 H17A 119.3
C16 C17 H17A 119.3
C17 C18 C19 121.5(3)
C17 C18 H18A 119.2
C19 C18 H18A 119.2
N2 C19 C18 122.7(3)
N2 C19 C14 120.0(2)
C18 C19 C14 117.2(3)
N2 C20 O3 111.7(2)
N2 C20 C11 113.8(2)
O3 C20 C11 107.6(2)
N2 C20 H20A 107.9
O3 C20 H20A 107.9
C11 C20 H20A 107.9
O3 C21 C22 111.4(3)
O3 C21 H21A 109.3
C22 C21 H21A 109.3
O3 C21 H21B 109.3
C22 C21 H21B 109.3
H21A C21 H21B 108.0
C21 C22 C23 108.5(2)
C21 C22 H22A 110.0
C23 C22 H22A 110.0
C21 C22 H22B 110.0
C23 C22 H22B 110.0
H22A C22 H22B 108.4
N2 C23 C22 109.8(2)
N2 C23 H23A 109.7
C22 C23 H23A 109.7
N2 C23 H23B 109.7
C22 C23 H23B 109.7
H23A C23 H23B 108.2
N1 C24 H24A 109.5
N1 C24 H24B 109.5
H24A C24 H24B 109.5
N1 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
N1 C25 H25A 109.5
N1 C25 H25B 109.5
H25A C25 H25B 109.5
N1 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.366(3)
O1 C1 1.387(3)
O2 C9 1.210(3)
O3 C21 1.431(3)
O3 C20 1.451(3)
N1 C3 1.383(4)
N1 C25 1.427(4)
N1 C24 1.446(4)
N2 C19 1.398(4)
N2 C20 1.429(4)
N2 C23 1.477(4)
C1 C2 1.374(4)
C1 C6 1.393(3)
C2 C3 1.402(4)
C2 H2A 0.9300
C3 C4 1.414(4)
C4 C5 1.373(4)
C4 H4A 0.9300
C5 C6 1.393(4)
C5 H5A 0.9300
C6 C7 1.462(3)
C7 C13 1.402(3)
C7 C8 1.403(3)
C8 C10 1.390(4)
C8 C9 1.464(4)
C10 C11 1.387(4)
C10 H10A 0.9300
C11 C12 1.418(4)
C11 C20 1.481(4)
C12 C13 1.395(3)
C12 C14 1.468(4)
C13 H13A 0.9300
C14 C15 1.387(4)
C14 C19 1.428(4)
C15 C16 1.384(4)
C15 H15A 0.9300
C16 C17 1.374(5)
C16 H16A 0.9300
C17 C18 1.366(5)
C17 H17A 0.9300
C18 C19 1.419(4)
C18 H18A 0.9300
C20 H20A 0.9800
C21 C22 1.507(5)
C21 H21A 0.9700
C21 H21B 0.9700
C22 C23 1.526(4)
C22 H22A 0.9700
C22 H22B 0.9700
C23 H23A 0.9700
C23 H23B 0.9700
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C25 H25A 0.9600
C25 H25B 0.9600
C25 H25C 0.9600
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 1.000 141 41 ' '
2 0.500 0.500 0.500 141 41 ' '
|
1502040.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502040.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502040
loop_
_publ_author_name
'Chen, Jiun-Jia'
'Li, Kuan-Ting'
'Yang, Ding-Yah'
_publ_section_title
;
Synthesis of coumarin/phenanthridine-fused heterocycles and their
photochemical and thermochromic properties.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1658
_journal_page_last 1661
_journal_paper_doi 10.1021/ol200117b
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C23 H19 N2 O2, I'
_chemical_formula_sum 'C23 H19 I N2 O2'
_chemical_formula_weight 482.30
_space_group_IT_number 11
_symmetry_cell_setting monoclinic
_symmetry_Int_Tables_number 11
_symmetry_space_group_name_Hall '-P 2yb'
_symmetry_space_group_name_H-M 'P 1 21/m 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 93.7180(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 11.9980(10)
_cell_length_b 6.7769(6)
_cell_length_c 11.9999(10)
_cell_measurement_reflns_used 3612
_cell_measurement_temperature 297(2)
_cell_measurement_theta_max 25.997
_cell_measurement_theta_min 2.326
_cell_volume 973.65(14)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SHELXTL'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0242
_diffrn_reflns_av_sigmaI/netI 0.0190
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 5511
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 2.33
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 1.666
_exptl_absorpt_correction_T_max 1.000000
_exptl_absorpt_correction_T_min 0.815662
_exptl_absorpt_correction_type empirical
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.645
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 480
_exptl_crystal_size_max 0.62
_exptl_crystal_size_mid 0.37
_exptl_crystal_size_min 0.11
_refine_diff_density_max 0.715
_refine_diff_density_min -0.818
_refine_diff_density_rms 0.070
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 179
_refine_ls_number_reflns 2067
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.050
_refine_ls_R_factor_all 0.0394
_refine_ls_R_factor_gt 0.0346
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.9398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0967
_refine_ls_wR_factor_ref 0.1004
_reflns_number_gt 1830
_reflns_number_total 2067
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200117b_si_005.cif
_cod_data_source_block jj078m
_cod_original_sg_symbol_H-M 'P 21/m'
_cod_database_code 1502040
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.84593(3) -0.2500 0.83800(3) 0.06457(18) Uani 1 2 d S
O1 O 0.4834(2) -0.2500 0.6473(2) 0.0513(8) Uani 1 2 d S
O2 O 0.5050(3) -0.2500 0.4683(3) 0.0791(14) Uani 1 2 d S
N1 N 0.4660(3) -0.2500 1.0413(3) 0.0498(10) Uani 1 2 d S
N2 N 0.0101(3) -0.2500 0.2451(3) 0.0387(8) Uani 1 2 d S
C1 C 0.4148(3) -0.2500 0.7365(3) 0.0364(8) Uani 1 2 d S
C2 C 0.4715(3) -0.2500 0.8406(3) 0.0371(9) Uani 1 2 d S
H2A H 0.5492 -0.2500 0.8461 0.044 Uiso 1 2 calc SR
C3 C 0.4130(4) -0.2500 0.9370(3) 0.0390(9) Uani 1 2 d S
C4 C 0.2935(3) -0.2500 0.9236(3) 0.0410(9) Uani 1 2 d S
H4A H 0.2518 -0.2500 0.9863 0.049 Uiso 1 2 calc SR
C5 C 0.2401(3) -0.2500 0.8186(3) 0.0391(9) Uani 1 2 d S
H5A H 0.1624 -0.2500 0.8123 0.047 Uiso 1 2 calc SR
C6 C 0.2976(3) -0.2500 0.7211(3) 0.0335(8) Uani 1 2 d S
C7 C 0.2466(3) -0.2500 0.6079(3) 0.0339(8) Uani 1 2 d S
C8 C 0.3181(3) -0.2500 0.5194(3) 0.0383(9) Uani 1 2 d S
C9 C 0.4415(3) -0.2500 0.5398(3) 0.0492(12) Uani 1 2 d S
C10 C 0.1305(3) -0.2500 0.5831(3) 0.0322(8) Uani 1 2 d S
H10A H 0.0826 -0.2500 0.6410 0.039 Uiso 1 2 calc SR
C11 C 0.0864(3) -0.2500 0.4727(3) 0.0306(8) Uani 1 2 d S
C12 C 0.1597(3) -0.2500 0.3859(3) 0.0359(8) Uani 1 2 d S
C13 C 0.2767(3) -0.2500 0.4094(3) 0.0442(10) Uani 1 2 d S
H13A H 0.3249 -0.2500 0.3517 0.053 Uiso 1 2 calc SR
C14 C 0.1178(3) -0.2500 0.2729(3) 0.0414(10) Uani 1 2 d S
H14A H 0.1678 -0.2500 0.2169 0.050 Uiso 1 2 calc SR
C15 C -0.0690(3) -0.2500 0.3258(3) 0.0341(8) Uani 1 2 d S
C16 C -0.0326(3) -0.2500 0.4413(3) 0.0321(8) Uani 1 2 d S
C17 C -0.1137(3) -0.2500 0.5192(3) 0.0362(8) Uani 1 2 d S
H17A H -0.0918 -0.2500 0.5950 0.043 Uiso 1 2 calc SR
C18 C -0.2263(3) -0.2500 0.4860(4) 0.0399(9) Uani 1 2 d S
H18A H -0.2793 -0.2500 0.5393 0.048 Uiso 1 2 calc SR
C19 C -0.2603(3) -0.2500 0.3731(4) 0.0435(10) Uani 1 2 d S
H19A H -0.3361 -0.2500 0.3512 0.052 Uiso 1 2 calc SR
C20 C -0.1832(4) -0.2500 0.2938(4) 0.0411(9) Uani 1 2 d S
H20A H -0.2068 -0.2500 0.2185 0.049 Uiso 1 2 calc SR
C21 C 0.5878(4) -0.2500 1.0558(4) 0.0511(12) Uani 1 2 d S
H21A H 0.6163 -0.1398 1.0219 0.079(13) Uiso 1 1 d R
H21C H 0.6109 -0.2500 1.1339 0.095 Uiso 1 2 d SR
C22 C 0.4036(4) -0.2500 1.1405(4) 0.0555(13) Uani 1 2 d S
H22A H 0.3579 -0.1294 1.1473 0.068(12) Uiso 1 1 d R
H22B H 0.4418 -0.2500 1.2039 0.09(2) Uiso 1 2 d SR
C23 C -0.0272(4) -0.2500 0.1246(4) 0.0545(13) Uani 1 2 d S
H23A H -0.071(3) -0.134(6) 0.107(3) 0.069(12) Uiso 1 1 d .
H23B H 0.035(5) -0.2500 0.078(6) 0.08(2) Uiso 1 2 d S
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0804(3) 0.0782(3) 0.0350(2) 0.000 0.00228(15) 0.000
O1 0.0253(14) 0.094(3) 0.0342(15) 0.000 0.0030(11) 0.000
O2 0.0282(15) 0.173(5) 0.0365(18) 0.000 0.0104(14) 0.000
N1 0.040(2) 0.080(3) 0.0287(18) 0.000 -0.0034(15) 0.000
N2 0.0364(17) 0.055(2) 0.0247(16) 0.000 -0.0006(13) 0.000
C1 0.0306(19) 0.047(2) 0.0325(19) 0.000 0.0079(15) 0.000
C2 0.0287(19) 0.047(2) 0.035(2) 0.000 -0.0017(15) 0.000
C3 0.042(2) 0.044(2) 0.031(2) 0.000 -0.0015(16) 0.000
C4 0.036(2) 0.058(3) 0.030(2) 0.000 0.0023(16) 0.000
C5 0.033(2) 0.053(2) 0.0310(19) 0.000 0.0049(16) 0.000
C6 0.0296(18) 0.041(2) 0.0295(19) 0.000 -0.0003(15) 0.000
C7 0.0310(19) 0.041(2) 0.0295(18) 0.000 0.0011(15) 0.000
C8 0.0272(19) 0.058(3) 0.0301(19) 0.000 0.0040(15) 0.000
C9 0.026(2) 0.093(4) 0.029(2) 0.000 0.0060(15) 0.000
C10 0.0301(19) 0.040(2) 0.0264(18) 0.000 0.0038(14) 0.000
C11 0.0269(18) 0.0362(19) 0.0288(18) 0.000 0.0032(14) 0.000
C12 0.0317(19) 0.049(2) 0.0265(19) 0.000 0.0004(15) 0.000
C13 0.034(2) 0.071(3) 0.028(2) 0.000 0.0072(16) 0.000
C14 0.037(2) 0.062(3) 0.0250(18) 0.000 0.0063(16) 0.000
C15 0.033(2) 0.041(2) 0.0277(18) 0.000 0.0010(15) 0.000
C16 0.0332(19) 0.0340(19) 0.0290(18) 0.000 0.0014(15) 0.000
C17 0.033(2) 0.045(2) 0.0305(19) 0.000 0.0022(15) 0.000
C18 0.0290(19) 0.053(2) 0.038(2) 0.000 0.0074(16) 0.000
C19 0.0259(19) 0.057(3) 0.047(2) 0.000 -0.0010(17) 0.000
C20 0.035(2) 0.052(2) 0.036(2) 0.000 -0.0041(17) 0.000
C21 0.043(2) 0.065(3) 0.044(2) 0.000 -0.011(2) 0.000
C22 0.053(3) 0.084(4) 0.029(2) 0.000 0.003(2) 0.000
C23 0.049(3) 0.092(4) 0.021(2) 0.000 -0.0020(18) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O1 C1 122.1(3)
C3 N1 C22 121.2(4)
C3 N1 C21 120.8(4)
C22 N1 C21 118.0(4)
C14 N2 C15 121.7(3)
C14 N2 C23 118.5(4)
C15 N2 C23 119.9(3)
C2 C1 O1 114.4(3)
C2 C1 C6 123.3(4)
O1 C1 C6 122.3(3)
C1 C2 C3 120.4(4)
C1 C2 H2A 119.8
C3 C2 H2A 119.8
N1 C3 C2 122.1(4)
N1 C3 C4 120.4(4)
C2 C3 C4 117.5(4)
C5 C4 C3 120.4(4)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C6 C5 C4 122.8(4)
C6 C5 H5A 118.6
C4 C5 H5A 118.6
C5 C6 C1 115.7(3)
C5 C6 C7 125.6(4)
C1 C6 C7 118.7(3)
C10 C7 C8 119.0(3)
C10 C7 C6 123.4(3)
C8 C7 C6 117.7(3)
C13 C8 C7 121.5(4)
C13 C8 C9 116.8(4)
C7 C8 C9 121.7(3)
O2 C9 O1 118.3(4)
O2 C9 C8 124.2(4)
O1 C9 C8 117.5(3)
C7 C10 C11 120.8(3)
C7 C10 H10A 119.6
C11 C10 H10A 119.6
C12 C11 C10 119.1(3)
C12 C11 C16 117.3(3)
C10 C11 C16 123.6(3)
C11 C12 C13 120.8(3)
C11 C12 C14 120.6(3)
C13 C12 C14 118.6(4)
C8 C13 C12 118.8(4)
C8 C13 H13A 120.6
C12 C13 H13A 120.6
N2 C14 C12 121.8(4)
N2 C14 H14A 119.1
C12 C14 H14A 119.1
C20 C15 N2 120.5(3)
C20 C15 C16 120.0(4)
N2 C15 C16 119.6(3)
C17 C16 C15 118.0(3)
C17 C16 C11 122.9(4)
C15 C16 C11 119.1(3)
C18 C17 C16 121.2(4)
C18 C17 H17A 119.4
C16 C17 H17A 119.4
C19 C18 C17 120.0(4)
C19 C18 H18A 120.0
C17 C18 H18A 120.0
C18 C19 C20 120.6(4)
C18 C19 H19A 119.7
C20 C19 H19A 119.7
C19 C20 C15 120.2(4)
C19 C20 H20A 119.9
C15 C20 H20A 119.9
N1 C21 H21A 110.0
N1 C21 H21C 109.9
H21A C21 H21C 109.7
N1 C22 H22A 112.8
N1 C22 H22B 116.9
H22A C22 H22B 101.0
N2 C23 H23A 110(2)
N2 C23 H23B 112(4)
H23A C23 H23B 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.354(5)
O1 C1 1.392(5)
O2 C9 1.184(5)
N1 C3 1.366(5)
N1 C22 1.447(6)
N1 C21 1.461(6)
N2 C14 1.312(5)
N2 C15 1.399(5)
N2 C23 1.486(5)
C1 C2 1.383(6)
C1 C6 1.406(6)
C2 C3 1.392(6)
C2 H2A 0.9300
C3 C4 1.432(6)
C4 C5 1.377(6)
C4 H4A 0.9300
C5 C6 1.396(5)
C5 H5A 0.9300
C6 C7 1.453(5)
C7 C10 1.405(5)
C7 C8 1.409(5)
C8 C13 1.380(6)
C8 C9 1.484(5)
C10 C11 1.395(5)
C10 H10A 0.9300
C11 C12 1.407(5)
C11 C16 1.453(5)
C12 C13 1.414(6)
C12 C14 1.414(5)
C13 H13A 0.9300
C14 H14A 0.9300
C15 C20 1.398(6)
C15 C16 1.425(5)
C16 C17 1.392(6)
C17 C18 1.384(6)
C17 H17A 0.9300
C18 C19 1.389(6)
C18 H18A 0.9300
C19 C20 1.370(6)
C19 H19A 0.9300
C20 H20A 0.9300
C21 H21A 0.9261
C21 H21C 0.9600
C22 H22A 0.9907
C22 H22B 0.8630
C23 H23A 0.96(4)
C23 H23B 0.96(7)
|
1502041.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502041.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502041
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C19 H21 Br O S'
_chemical_formula_sum 'C19 H21 Br O S'
_chemical_formula_weight 377.33
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 109.340(10)
_cell_angle_beta 93.580(11)
_cell_angle_gamma 101.960(12)
_cell_formula_units_Z 2
_cell_length_a 5.7147(13)
_cell_length_b 11.254(2)
_cell_length_c 14.617(3)
_cell_measurement_reflns_used 435
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 2.17
_cell_volume 859.0(3)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material 'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Saturn724+ CCD'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0405
_diffrn_reflns_av_sigmaI/netI 0.0415
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 11480
_diffrn_reflns_theta_full 27.49
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_min 2.87
_exptl_absorpt_coefficient_mu 2.514
_exptl_absorpt_correction_T_max 0.6333
_exptl_absorpt_correction_T_min 0.5293
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.459
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 388
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.415
_refine_diff_density_min -0.246
_refine_diff_density_rms 0.066
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.105
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 200
_refine_ls_number_reflns 3931
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.105
_refine_ls_R_factor_all 0.0485
_refine_ls_R_factor_gt 0.0430
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.6615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0828
_refine_ls_wR_factor_ref 0.0854
_reflns_number_gt 3584
_reflns_number_total 3931
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_002.cif
_cod_data_source_block a
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 1.13176(5) 0.60630(3) 0.88771(2) 0.03955(10) Uani 1 1 d .
O1 O 0.6606(3) 0.34639(17) 0.47072(13) 0.0292(4) Uani 1 1 d .
C1 C 0.7523(4) 0.4099(2) 0.56745(18) 0.0249(5) Uani 1 1 d .
C2 C 0.6522(4) 0.4982(2) 0.63269(19) 0.0273(5) Uani 1 1 d .
H2A H 0.5097 0.5193 0.6126 0.033 Uiso 1 1 calc R
C3 C 0.7672(5) 0.5555(3) 0.72915(19) 0.0290(6) Uani 1 1 d .
H3A H 0.7035 0.6169 0.7762 0.035 Uiso 1 1 calc R
C4 C 0.9744(4) 0.5228(2) 0.75625(18) 0.0274(5) Uani 1 1 d .
C5 C 1.0730(4) 0.4326(2) 0.69092(19) 0.0273(5) Uani 1 1 d .
H5A H 1.2138 0.4103 0.7113 0.033 Uiso 1 1 calc R
C6 C 0.9595(4) 0.3760(2) 0.59482(19) 0.0255(5) Uani 1 1 d .
C7 C 1.0139(5) 0.2762(3) 0.50596(19) 0.0320(6) Uani 1 1 d .
H7A H 0.9776 0.1888 0.5111 0.038 Uiso 1 1 calc R
H7B H 1.1849 0.2997 0.4962 0.038 Uiso 1 1 calc R
C8 C 0.8419(5) 0.2821(2) 0.42320(18) 0.0278(5) Uani 1 1 d .
H8A H 0.9361 0.3385 0.3911 0.033 Uiso 1 1 calc R
C9 C 0.7114(4) 0.1547(2) 0.34388(18) 0.0259(5) Uani 1 1 d .
H9A H 0.8365 0.1132 0.3103 0.031 Uiso 1 1 calc R
C10 C 0.7107(5) -0.0805(3) 0.37789(19) 0.0304(6) Uani 1 1 d .
H10A H 0.8826 -0.0379 0.4045 0.036 Uiso 1 1 calc R
H10B H 0.6504 -0.1369 0.4152 0.036 Uiso 1 1 calc R
C11 C 0.6943(5) -0.1636(2) 0.27238(18) 0.0266(5) Uani 1 1 d .
C12 C 0.8894(5) -0.1497(3) 0.2217(2) 0.0321(6) Uani 1 1 d .
H12A H 1.0365 -0.0884 0.2545 0.039 Uiso 1 1 calc R
C13 C 0.8715(5) -0.2248(3) 0.1238(2) 0.0374(6) Uani 1 1 d .
H13A H 1.0061 -0.2141 0.0897 0.045 Uiso 1 1 calc R
C14 C 0.6598(5) -0.3148(3) 0.0752(2) 0.0372(7) Uani 1 1 d .
H14A H 0.6473 -0.3655 0.0079 0.045 Uiso 1 1 calc R
C15 C 0.4655(5) -0.3302(3) 0.1259(2) 0.0356(6) Uani 1 1 d .
H15A H 0.3199 -0.3929 0.0933 0.043 Uiso 1 1 calc R
C16 C 0.4817(5) -0.2551(3) 0.2236(2) 0.0308(6) Uani 1 1 d .
H16A H 0.3469 -0.2661 0.2575 0.037 Uiso 1 1 calc R
C17 C 0.5461(5) 0.1746(3) 0.26644(19) 0.0309(6) Uani 1 1 d .
H17A H 0.3978 0.1930 0.2937 0.037 Uiso 1 1 calc R
H17B H 0.6293 0.2516 0.2524 0.037 Uiso 1 1 calc R
C18 C 0.4738(5) 0.0591(3) 0.17075(19) 0.0358(6) Uani 1 1 d .
H18A H 0.4015 -0.0197 0.1849 0.043 Uiso 1 1 calc R
H18B H 0.6202 0.0450 0.1401 0.043 Uiso 1 1 calc R
C19 C 0.2935(6) 0.0785(3) 0.0988(2) 0.0485(8) Uani 1 1 d .
H19A H 0.2543 0.0026 0.0381 0.073 Uiso 1 1 calc R
H19B H 0.3645 0.1561 0.0841 0.073 Uiso 1 1 calc R
H19C H 0.1457 0.0894 0.1278 0.073 Uiso 1 1 calc R
S1 S 0.54018(12) 0.04401(6) 0.39711(5) 0.02697(15) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03974(17) 0.04783(19) 0.02614(15) 0.00836(12) 0.00024(11) 0.00907(14)
O1 0.0281(9) 0.0295(10) 0.0273(9) 0.0048(8) -0.0014(7) 0.0115(8)
C1 0.0225(12) 0.0237(12) 0.0275(12) 0.0107(10) 0.0007(10) 0.0016(10)
C2 0.0230(12) 0.0289(13) 0.0329(13) 0.0125(11) 0.0056(10) 0.0093(11)
C3 0.0302(13) 0.0284(14) 0.0295(13) 0.0099(11) 0.0081(11) 0.0086(11)
C4 0.0252(12) 0.0290(13) 0.0250(12) 0.0092(11) 0.0015(10) 0.0013(11)
C5 0.0207(12) 0.0301(14) 0.0325(13) 0.0139(11) 0.0013(10) 0.0051(10)
C6 0.0221(12) 0.0232(12) 0.0320(13) 0.0114(11) 0.0037(10) 0.0050(10)
C7 0.0250(13) 0.0323(14) 0.0334(14) 0.0049(12) -0.0022(11) 0.0088(11)
C8 0.0259(13) 0.0285(13) 0.0290(13) 0.0090(11) 0.0050(10) 0.0080(11)
C9 0.0269(13) 0.0269(13) 0.0250(12) 0.0104(10) 0.0054(10) 0.0065(11)
C10 0.0348(14) 0.0312(14) 0.0283(13) 0.0124(11) 0.0027(11) 0.0122(12)
C11 0.0292(13) 0.0243(12) 0.0285(13) 0.0102(10) 0.0015(10) 0.0101(11)
C12 0.0270(13) 0.0289(14) 0.0359(14) 0.0054(12) 0.0026(11) 0.0076(11)
C13 0.0343(15) 0.0375(16) 0.0388(15) 0.0083(13) 0.0134(12) 0.0114(13)
C14 0.0428(16) 0.0329(15) 0.0304(14) 0.0020(12) 0.0012(12) 0.0139(13)
C15 0.0310(14) 0.0285(14) 0.0398(15) 0.0043(12) -0.0015(12) 0.0060(12)
C16 0.0275(13) 0.0307(14) 0.0367(14) 0.0139(12) 0.0082(11) 0.0081(11)
C17 0.0349(14) 0.0312(14) 0.0284(13) 0.0145(11) 0.0006(11) 0.0061(12)
C18 0.0388(15) 0.0412(16) 0.0247(13) 0.0095(12) 0.0018(12) 0.0082(13)
C19 0.0512(19) 0.055(2) 0.0339(16) 0.0153(15) -0.0080(14) 0.0050(16)
S1 0.0305(3) 0.0265(3) 0.0250(3) 0.0096(3) 0.0078(3) 0.0075(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C8 107.35(18)
O1 C1 C2 124.4(2)
O1 C1 C6 113.1(2)
C2 C1 C6 122.5(2)
C1 C2 C3 117.7(2)
C1 C2 H2A 121.1
C3 C2 H2A 121.1
C4 C3 C2 119.8(2)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 122.4(2)
C3 C4 Br1 118.70(19)
C5 C4 Br1 118.87(19)
C6 C5 C4 117.8(2)
C6 C5 H5A 121.1
C4 C5 H5A 121.1
C5 C6 C1 119.7(2)
C5 C6 C7 132.3(2)
C1 C6 C7 108.0(2)
C6 C7 C8 101.9(2)
C6 C7 H7A 111.4
C8 C7 H7A 111.4
C6 C7 H7B 111.4
C8 C7 H7B 111.4
H7A C7 H7B 109.2
O1 C8 C9 108.4(2)
O1 C8 C7 106.2(2)
C9 C8 C7 117.6(2)
O1 C8 H8A 108.1
C9 C8 H8A 108.1
C7 C8 H8A 108.1
C8 C9 C17 112.2(2)
C8 C9 S1 110.81(17)
C17 C9 S1 110.50(18)
C8 C9 H9A 107.7
C17 C9 H9A 107.7
S1 C9 H9A 107.7
C11 C10 S1 113.75(18)
C11 C10 H10A 108.8
S1 C10 H10A 108.8
C11 C10 H10B 108.8
S1 C10 H10B 108.8
H10A C10 H10B 107.7
C12 C11 C16 118.9(2)
C12 C11 C10 120.7(2)
C16 C11 C10 120.3(2)
C13 C12 C11 120.5(3)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C14 C13 C12 120.5(3)
C14 C13 H13A 119.7
C12 C13 H13A 119.7
C13 C14 C15 119.2(3)
C13 C14 H14A 120.4
C15 C14 H14A 120.4
C16 C15 C14 120.6(3)
C16 C15 H15A 119.7
C14 C15 H15A 119.7
C15 C16 C11 120.3(3)
C15 C16 H16A 119.9
C11 C16 H16A 119.9
C18 C17 C9 114.1(2)
C18 C17 H17A 108.7
C9 C17 H17A 108.7
C18 C17 H17B 108.7
C9 C17 H17B 108.7
H17A C17 H17B 107.6
C17 C18 C19 112.4(2)
C17 C18 H18A 109.1
C19 C18 H18A 109.1
C17 C18 H18B 109.1
C19 C18 H18B 109.1
H18A C18 H18B 107.9
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C10 S1 C9 102.48(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.903(3)
O1 C1 1.367(3)
O1 C8 1.465(3)
C1 C2 1.379(3)
C1 C6 1.392(3)
C2 C3 1.394(4)
C2 H2A 0.9500
C3 C4 1.384(4)
C3 H3A 0.9500
C4 C5 1.386(3)
C5 C6 1.386(3)
C5 H5A 0.9500
C6 C7 1.508(3)
C7 C8 1.538(4)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.518(3)
C8 H8A 1.0000
C9 C17 1.531(3)
C9 S1 1.829(3)
C9 H9A 1.0000
C10 C11 1.501(3)
C10 S1 1.825(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.387(4)
C11 C16 1.390(4)
C12 C13 1.385(4)
C12 H12A 0.9500
C13 C14 1.379(4)
C13 H13A 0.9500
C14 C15 1.386(4)
C14 H14A 0.9500
C15 C16 1.383(4)
C15 H15A 0.9500
C16 H16A 0.9500
C17 C18 1.522(4)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.526(4)
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 O1 C1 C2 169.1(2)
C8 O1 C1 C6 -11.2(3)
O1 C1 C2 C3 -179.7(2)
C6 C1 C2 C3 0.6(4)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -0.9(4)
C2 C3 C4 Br1 178.34(19)
C3 C4 C5 C6 1.2(4)
Br1 C4 C5 C6 -178.04(18)
C4 C5 C6 C1 -0.6(4)
C4 C5 C6 C7 -179.7(3)
O1 C1 C6 C5 -180.0(2)
C2 C1 C6 C5 -0.3(4)
O1 C1 C6 C7 -0.6(3)
C2 C1 C6 C7 179.0(2)
C5 C6 C7 C8 -169.4(3)
C1 C6 C7 C8 11.4(3)
C1 O1 C8 C9 145.3(2)
C1 O1 C8 C7 18.0(3)
C6 C7 C8 O1 -17.5(3)
C6 C7 C8 C9 -139.0(2)
O1 C8 C9 C17 59.6(3)
C7 C8 C9 C17 179.9(2)
O1 C8 C9 S1 -64.5(2)
C7 C8 C9 S1 55.9(3)
S1 C10 C11 C12 107.0(3)
S1 C10 C11 C16 -72.4(3)
C16 C11 C12 C13 0.8(4)
C10 C11 C12 C13 -178.6(3)
C11 C12 C13 C14 -0.3(4)
C12 C13 C14 C15 -0.6(4)
C13 C14 C15 C16 1.0(4)
C14 C15 C16 C11 -0.5(4)
C12 C11 C16 C15 -0.4(4)
C10 C11 C16 C15 179.0(2)
C8 C9 C17 C18 161.8(2)
S1 C9 C17 C18 -74.0(3)
C9 C17 C18 C19 175.4(2)
C11 C10 S1 C9 -68.9(2)
C8 C9 S1 C10 -109.74(19)
C17 C9 S1 C10 125.27(19)
|
1502042.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502042.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502042
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C19 H21 Br O S'
_chemical_formula_sum 'C19 H21 Br O S'
_chemical_formula_weight 377.33
_chemical_name_systematic
;
?
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 72.270(7)
_cell_angle_beta 82.260(8)
_cell_angle_gamma 76.860(7)
_cell_formula_units_Z 2
_cell_length_a 5.8183(9)
_cell_length_b 11.2510(15)
_cell_length_c 14.411(2)
_cell_measurement_reflns_used 543
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.48
_cell_measurement_theta_min 2.17
_cell_volume 872.9(2)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material 'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Saturn724+ CCD'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0372
_diffrn_reflns_av_sigmaI/netI 0.0383
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 11709
_diffrn_reflns_theta_full 27.47
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_min 2.76
_exptl_absorpt_coefficient_mu 2.474
_exptl_absorpt_correction_T_max 0.6375
_exptl_absorpt_correction_T_min 0.4378
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.436
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description palte
_exptl_crystal_F_000 388
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.765
_refine_diff_density_min -0.292
_refine_diff_density_rms 0.064
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.114
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 200
_refine_ls_number_reflns 3989
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.114
_refine_ls_R_factor_all 0.0517
_refine_ls_R_factor_gt 0.0463
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.5636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0967
_refine_ls_wR_factor_ref 0.0994
_reflns_number_gt 3648
_reflns_number_total 3989
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_003.cif
_cod_data_source_block sa660
_cod_original_sg_symbol_H-M P-1
_cod_database_code 1502042
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.88002(6) 0.29795(3) -0.34736(2) 0.04857(12) Uani 1 1 d .
S1 S 0.98858(12) 0.36285(6) 0.10056(5) 0.03332(16) Uani 1 1 d .
O1 O 1.2238(3) 0.10648(17) 0.05733(13) 0.0311(4) Uani 1 1 d .
C1 C 0.9849(5) 0.2410(2) -0.2189(2) 0.0327(6) Uani 1 1 d .
C2 C 1.2211(5) 0.1851(2) -0.2055(2) 0.0334(6) Uani 1 1 d .
H2A H 1.3301 0.1777 -0.2598 0.040 Uiso 1 1 calc R
C3 C 1.2941(4) 0.1404(2) -0.11169(19) 0.0301(5) Uani 1 1 d .
H3A H 1.4550 0.1018 -0.1010 0.036 Uiso 1 1 calc R
C4 C 1.1324(4) 0.1517(2) -0.03237(19) 0.0273(5) Uani 1 1 d .
C5 C 0.8970(4) 0.2095(2) -0.04623(19) 0.0285(5) Uani 1 1 d .
C6 C 0.8247(5) 0.2548(2) -0.1410(2) 0.0331(6) Uani 1 1 d .
H6A H 0.6648 0.2953 -0.1522 0.040 Uiso 1 1 calc R
C7 C 1.0608(4) 0.1021(2) 0.14332(19) 0.0304(5) Uani 1 1 d .
H7A H 0.9866 0.0262 0.1563 0.036 Uiso 1 1 calc R
C8 C 0.8651(4) 0.2202(2) 0.1260(2) 0.0300(5) Uani 1 1 d .
H8A H 0.7546 0.2140 0.1860 0.036 Uiso 1 1 calc R
C9 C 0.7283(4) 0.2236(3) 0.0408(2) 0.0341(6) Uani 1 1 d .
H9A H 0.6388 0.1537 0.0613 0.041 Uiso 1 1 calc R
H9B H 0.6137 0.3053 0.0225 0.041 Uiso 1 1 calc R
C10 C 1.2154(5) 0.0796(3) 0.22599(19) 0.0363(6) Uani 1 1 d .
H10A H 1.3051 0.1492 0.2092 0.044 Uiso 1 1 calc R
H10B H 1.3317 -0.0008 0.2303 0.044 Uiso 1 1 calc R
C11 C 1.0869(6) 0.0720(3) 0.3262(2) 0.0456(7) Uani 1 1 d .
H11A H 0.9741 0.0139 0.3393 0.055 Uiso 1 1 calc R
H11B H 0.9957 0.1573 0.3275 0.055 Uiso 1 1 calc R
C12 C 1.2627(7) 0.0236(4) 0.4054(2) 0.0596(9) Uani 1 1 d .
H12A H 1.1793 0.0293 0.4681 0.089 Uiso 1 1 calc R
H12B H 1.3845 0.0756 0.3886 0.089 Uiso 1 1 calc R
H12C H 1.3371 -0.0653 0.4103 0.089 Uiso 1 1 calc R
C13 C 0.7263(5) 0.4730(3) 0.1310(2) 0.0398(7) Uani 1 1 d .
H13A H 0.7598 0.5601 0.1102 0.048 Uiso 1 1 calc R
H13B H 0.5942 0.4734 0.0940 0.048 Uiso 1 1 calc R
C14 C 0.6511(5) 0.4387(2) 0.2383(2) 0.0312(6) Uani 1 1 d .
C15 C 0.7793(5) 0.4613(3) 0.3034(2) 0.0356(6) Uani 1 1 d .
H15A H 0.9120 0.5008 0.2795 0.043 Uiso 1 1 calc R
C16 C 0.7166(5) 0.4273(3) 0.4024(2) 0.0421(7) Uani 1 1 d .
H16A H 0.8058 0.4437 0.4461 0.051 Uiso 1 1 calc R
C17 C 0.5243(6) 0.3694(3) 0.4381(2) 0.0447(7) Uani 1 1 d .
H17A H 0.4824 0.3447 0.5063 0.054 Uiso 1 1 calc R
C18 C 0.3948(5) 0.3480(3) 0.3742(2) 0.0452(7) Uani 1 1 d .
H18A H 0.2612 0.3094 0.3984 0.054 Uiso 1 1 calc R
C19 C 0.4564(5) 0.3820(3) 0.2747(2) 0.0396(7) Uani 1 1 d .
H19A H 0.3652 0.3665 0.2313 0.048 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0604(2) 0.04433(19) 0.03902(19) -0.00590(14) -0.02160(15) -0.00405(15)
S1 0.0388(4) 0.0249(3) 0.0348(4) -0.0091(3) 0.0037(3) -0.0060(3)
O1 0.0268(9) 0.0355(10) 0.0277(9) -0.0090(8) -0.0039(7) 0.0019(7)
C1 0.0393(14) 0.0246(12) 0.0348(14) -0.0050(11) -0.0121(12) -0.0067(11)
C2 0.0345(14) 0.0315(13) 0.0323(14) -0.0086(11) -0.0008(11) -0.0043(11)
C3 0.0268(12) 0.0269(12) 0.0352(14) -0.0071(11) -0.0050(11) -0.0032(10)
C4 0.0270(12) 0.0201(11) 0.0330(13) -0.0057(10) -0.0040(10) -0.0027(9)
C5 0.0246(12) 0.0237(12) 0.0367(14) -0.0069(11) -0.0039(11) -0.0051(9)
C6 0.0260(12) 0.0280(13) 0.0442(16) -0.0075(12) -0.0099(11) -0.0027(10)
C7 0.0304(13) 0.0256(12) 0.0320(14) -0.0059(11) 0.0027(11) -0.0054(10)
C8 0.0274(12) 0.0260(12) 0.0337(14) -0.0073(11) 0.0022(11) -0.0036(10)
C9 0.0223(12) 0.0356(14) 0.0415(16) -0.0107(12) -0.0008(11) -0.0008(10)
C10 0.0374(14) 0.0344(14) 0.0304(14) -0.0053(12) -0.0026(12) 0.0010(12)
C11 0.0506(18) 0.0508(18) 0.0311(15) -0.0069(14) 0.0007(13) -0.0098(15)
C12 0.077(3) 0.066(2) 0.0309(16) -0.0062(16) -0.0075(16) -0.0122(19)
C13 0.0495(17) 0.0285(13) 0.0357(15) -0.0107(12) -0.0047(13) 0.0065(12)
C14 0.0335(13) 0.0233(12) 0.0338(14) -0.0094(11) -0.0051(11) 0.0039(10)
C15 0.0348(14) 0.0329(14) 0.0405(16) -0.0123(12) -0.0037(12) -0.0063(11)
C16 0.0452(17) 0.0464(17) 0.0366(16) -0.0172(14) -0.0093(13) -0.0014(13)
C17 0.0500(18) 0.0415(16) 0.0329(15) -0.0055(13) -0.0001(13) 0.0014(14)
C18 0.0356(15) 0.0413(16) 0.058(2) -0.0168(15) 0.0071(14) -0.0084(13)
C19 0.0333(14) 0.0420(16) 0.0490(17) -0.0235(14) -0.0077(13) -0.0012(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 S1 C13 99.86(13)
C4 O1 C7 118.21(19)
C6 C1 C2 121.5(2)
C6 C1 Br1 119.6(2)
C2 C1 Br1 119.0(2)
C3 C2 C1 118.6(3)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C2 C3 C4 120.3(2)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
O1 C4 C5 123.4(2)
O1 C4 C3 115.7(2)
C5 C4 C3 120.9(2)
C4 C5 C6 118.5(2)
C4 C5 C9 119.6(2)
C6 C5 C9 121.9(2)
C1 C6 C5 120.2(2)
C1 C6 H6A 119.9
C5 C6 H6A 119.9
O1 C7 C10 104.9(2)
O1 C7 C8 110.7(2)
C10 C7 C8 116.7(2)
O1 C7 H7A 108.1
C10 C7 H7A 108.1
C8 C7 H7A 108.1
C7 C8 C9 108.2(2)
C7 C8 S1 110.45(17)
C9 C8 S1 111.53(18)
C7 C8 H8A 108.9
C9 C8 H8A 108.9
S1 C8 H8A 108.9
C5 C9 C8 110.3(2)
C5 C9 H9A 109.6
C8 C9 H9A 109.6
C5 C9 H9B 109.6
C8 C9 H9B 109.6
H9A C9 H9B 108.1
C7 C10 C11 116.0(2)
C7 C10 H10A 108.3
C11 C10 H10A 108.3
C7 C10 H10B 108.3
C11 C10 H10B 108.3
H10A C10 H10B 107.4
C10 C11 C12 110.6(3)
C10 C11 H11A 109.5
C12 C11 H11A 109.5
C10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.1
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 S1 112.79(19)
C14 C13 H13A 109.0
S1 C13 H13A 109.0
C14 C13 H13B 109.0
S1 C13 H13B 109.0
H13A C13 H13B 107.8
C15 C14 C19 118.5(3)
C15 C14 C13 120.1(3)
C19 C14 C13 121.3(3)
C16 C15 C14 120.9(3)
C16 C15 H15A 119.6
C14 C15 H15A 119.6
C15 C16 C17 120.1(3)
C15 C16 H16A 119.9
C17 C16 H16A 119.9
C18 C17 C16 119.4(3)
C18 C17 H17A 120.3
C16 C17 H17A 120.3
C17 C18 C19 120.8(3)
C17 C18 H18A 119.6
C19 C18 H18A 119.6
C18 C19 C14 120.2(3)
C18 C19 H19A 119.9
C14 C19 H19A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.901(3)
S1 C8 1.823(3)
S1 C13 1.830(3)
O1 C4 1.369(3)
O1 C7 1.451(3)
C1 C6 1.384(4)
C1 C2 1.388(4)
C2 C3 1.381(4)
C2 H2A 0.9500
C3 C4 1.397(4)
C3 H3A 0.9500
C4 C5 1.389(3)
C5 C6 1.391(4)
C5 C9 1.510(4)
C6 H6A 0.9500
C7 C10 1.514(4)
C7 C8 1.520(3)
C7 H7A 1.0000
C8 C9 1.536(4)
C8 H8A 1.0000
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.522(4)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.525(4)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.504(4)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.386(4)
C14 C19 1.390(4)
C15 C16 1.381(4)
C15 H15A 0.9500
C16 C17 1.383(4)
C16 H16A 0.9500
C17 C18 1.371(4)
C17 H17A 0.9500
C18 C19 1.385(4)
C18 H18A 0.9500
C19 H19A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.3(4)
Br1 C1 C2 C3 -178.00(19)
C1 C2 C3 C4 0.0(4)
C7 O1 C4 C5 9.2(3)
C7 O1 C4 C3 -173.1(2)
C2 C3 C4 O1 -178.9(2)
C2 C3 C4 C5 -1.1(4)
O1 C4 C5 C6 178.4(2)
C3 C4 C5 C6 0.8(4)
O1 C4 C5 C9 -0.6(4)
C3 C4 C5 C9 -178.2(2)
C2 C1 C6 C5 -1.6(4)
Br1 C1 C6 C5 177.71(19)
C4 C5 C6 C1 0.5(4)
C9 C5 C6 C1 179.5(2)
C4 O1 C7 C10 -166.7(2)
C4 O1 C7 C8 -40.0(3)
O1 C7 C8 C9 61.1(3)
C10 C7 C8 C9 -179.1(2)
O1 C7 C8 S1 -61.2(2)
C10 C7 C8 S1 58.6(3)
C13 S1 C8 C7 -158.79(19)
C13 S1 C8 C9 80.80(19)
C4 C5 C9 C8 23.2(3)
C6 C5 C9 C8 -155.8(2)
C7 C8 C9 C5 -51.9(3)
S1 C8 C9 C5 69.8(2)
O1 C7 C10 C11 179.5(2)
C8 C7 C10 C11 56.7(3)
C7 C10 C11 C12 168.9(3)
C8 S1 C13 C14 68.0(2)
S1 C13 C14 C15 74.4(3)
S1 C13 C14 C19 -104.4(3)
C19 C14 C15 C16 0.6(4)
C13 C14 C15 C16 -178.2(2)
C14 C15 C16 C17 0.2(4)
C15 C16 C17 C18 -1.0(4)
C16 C17 C18 C19 0.9(5)
C17 C18 C19 C14 -0.1(4)
C15 C14 C19 C18 -0.7(4)
C13 C14 C19 C18 178.2(2)
|
1502043.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502043.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502043
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C14 H20 O2 S'
_chemical_formula_sum 'C14 H20 O2 S'
_chemical_formula_weight 252.36
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 104.09(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.116(2)
_cell_length_b 6.5574(13)
_cell_length_c 17.062(3)
_cell_measurement_reflns_used 4053
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.4818
_cell_measurement_theta_min 1.7330
_cell_volume 1314.8(4)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type 'Saturn724+ CCD'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0463
_diffrn_reflns_av_sigmaI/netI 0.0398
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 11110
_diffrn_reflns_theta_full 27.49
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_min 1.73
_exptl_absorpt_coefficient_mu 0.234
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.6815
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour Colorless
_exptl_crystal_density_diffrn 1.275
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 544
_exptl_crystal_size_max 0.57
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.07
_refine_diff_density_max 0.354
_refine_diff_density_min -0.388
_refine_diff_density_rms 0.122
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.230
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 154
_refine_ls_number_reflns 2983
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.230
_refine_ls_R_factor_all 0.0683
_refine_ls_R_factor_gt 0.0614
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+0.7156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1709
_refine_ls_wR_factor_ref 0.1840
_reflns_number_gt 2769
_reflns_number_total 2983
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_004.cif
_cod_data_source_block a
_cod_original_cell_volume 1314.7(5)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502043
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.84665(5) 0.61477(9) 0.07390(4) 0.0254(2) Uani 1 1 d .
O1 O 0.54520(17) 0.3103(3) 0.14968(13) 0.0444(6) Uani 1 1 d .
H1 H 0.4874 0.2705 0.1151 0.053 Uiso 1 1 d R
O2 O 0.64587(15) 0.8612(3) -0.04130(12) 0.0348(5) Uani 1 1 d .
C1 C 0.6609(2) 0.8657(4) 0.04517(16) 0.0288(6) Uani 1 1 d .
H1A H 0.6271 0.9957 0.0594 0.035 Uiso 1 1 calc R
C2 C 0.7876(2) 0.8644(4) 0.08859(15) 0.0252(5) Uani 1 1 d .
H2A H 0.7948 0.8851 0.1477 0.030 Uiso 1 1 calc R
C3 C 0.8484(2) 1.0390(4) 0.05733(17) 0.0313(6) Uani 1 1 d .
H3A H 0.8228 1.1704 0.0753 0.038 Uiso 1 1 calc R
H3B H 0.9313 1.0271 0.0806 0.038 Uiso 1 1 calc R
C4 C 0.8247(2) 1.0373(4) -0.03450(17) 0.0334(6) Uani 1 1 d .
H4A H 0.8580 1.1606 -0.0532 0.040 Uiso 1 1 calc R
H4B H 0.8607 0.9161 -0.0524 0.040 Uiso 1 1 calc R
C5 C 0.6983(2) 1.0327(5) -0.07094(18) 0.0388(7) Uani 1 1 d .
H5A H 0.6637 1.1607 -0.0574 0.047 Uiso 1 1 calc R
H5B H 0.6839 1.0239 -0.1305 0.047 Uiso 1 1 calc R
C6 C 0.5907(2) 0.6893(4) 0.06551(16) 0.0299(6) Uani 1 1 d .
H6A H 0.6190 0.5605 0.0473 0.036 Uiso 1 1 calc R
H6B H 0.5107 0.7068 0.0348 0.036 Uiso 1 1 calc R
C7 C 0.5935(2) 0.6703(5) 0.15527(17) 0.0366(6) Uani 1 1 d .
H7A H 0.6719 0.6365 0.1857 0.044 Uiso 1 1 calc R
H7B H 0.5729 0.8032 0.1753 0.044 Uiso 1 1 calc R
C8 C 0.5127(3) 0.5081(5) 0.17123(19) 0.0410(7) Uani 1 1 d .
H8A H 0.5126 0.5094 0.2292 0.049 Uiso 1 1 calc R
H8B H 0.4346 0.5390 0.1396 0.049 Uiso 1 1 calc R
C9 C 0.9875(2) 0.6265(4) 0.13431(14) 0.0231(5) Uani 1 1 d .
C10 C 1.0258(2) 0.7622(4) 0.19834(15) 0.0280(5) Uani 1 1 d .
H10A H 0.9742 0.8554 0.2130 0.034 Uiso 1 1 calc R
C11 C 1.1392(2) 0.7607(4) 0.24044(16) 0.0333(6) Uani 1 1 d .
H11A H 1.1651 0.8553 0.2831 0.040 Uiso 1 1 calc R
C12 C 1.2151(2) 0.6233(4) 0.22114(16) 0.0315(6) Uani 1 1 d .
H12A H 1.2928 0.6244 0.2500 0.038 Uiso 1 1 calc R
C13 C 1.1769(2) 0.4845(4) 0.15961(16) 0.0315(6) Uani 1 1 d .
H13A H 1.2282 0.3872 0.1471 0.038 Uiso 1 1 calc R
C14 C 1.0641(2) 0.4864(4) 0.11590(15) 0.0274(5) Uani 1 1 d .
H14A H 1.0389 0.3916 0.0732 0.033 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0252(3) 0.0220(4) 0.0276(3) -0.0022(2) 0.0040(2) 0.0010(2)
O1 0.0358(11) 0.0403(12) 0.0508(13) 0.0125(10) -0.0017(9) -0.0019(9)
O2 0.0289(10) 0.0437(11) 0.0304(10) 0.0079(8) 0.0045(8) -0.0027(8)
C1 0.0268(12) 0.0300(13) 0.0306(13) 0.0016(10) 0.0088(10) 0.0046(10)
C2 0.0248(12) 0.0242(12) 0.0272(12) -0.0003(9) 0.0076(10) 0.0001(9)
C3 0.0329(13) 0.0222(13) 0.0383(14) 0.0007(11) 0.0079(11) -0.0033(10)
C4 0.0372(14) 0.0274(13) 0.0371(14) 0.0091(11) 0.0120(11) 0.0000(11)
C5 0.0369(15) 0.0418(17) 0.0372(15) 0.0146(13) 0.0084(12) 0.0025(12)
C6 0.0209(11) 0.0359(14) 0.0330(13) 0.0021(11) 0.0067(10) -0.0009(10)
C7 0.0358(15) 0.0429(16) 0.0332(14) -0.0015(12) 0.0127(12) -0.0029(12)
C8 0.0368(15) 0.0488(18) 0.0398(16) 0.0059(13) 0.0140(12) -0.0042(13)
C9 0.0264(12) 0.0227(12) 0.0212(11) 0.0034(9) 0.0076(9) 0.0002(9)
C10 0.0294(12) 0.0308(14) 0.0247(12) -0.0008(10) 0.0080(10) 0.0003(10)
C11 0.0376(14) 0.0367(15) 0.0249(12) -0.0024(11) 0.0063(11) -0.0016(11)
C12 0.0271(13) 0.0368(15) 0.0278(13) 0.0051(11) 0.0010(10) -0.0002(10)
C13 0.0283(12) 0.0321(14) 0.0335(14) 0.0026(11) 0.0064(10) 0.0039(10)
C14 0.0286(12) 0.0260(13) 0.0287(12) 0.0006(10) 0.0093(10) -0.0006(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 S1 C2 103.64(11)
C8 O1 H1 103.2
C5 O2 C1 112.7(2)
O2 C1 C6 106.2(2)
O2 C1 C2 110.9(2)
C6 C1 C2 115.7(2)
O2 C1 H1A 107.9
C6 C1 H1A 107.9
C2 C1 H1A 107.9
C3 C2 C1 109.8(2)
C3 C2 S1 112.66(17)
C1 C2 S1 108.56(17)
C3 C2 H2A 108.6
C1 C2 H2A 108.6
S1 C2 H2A 108.6
C4 C3 C2 111.6(2)
C4 C3 H3A 109.3
C2 C3 H3A 109.3
C4 C3 H3B 109.3
C2 C3 H3B 109.3
H3A C3 H3B 108.0
C5 C4 C3 110.0(2)
C5 C4 H4A 109.7
C3 C4 H4A 109.7
C5 C4 H4B 109.7
C3 C4 H4B 109.7
H4A C4 H4B 108.2
O2 C5 C4 111.2(2)
O2 C5 H5A 109.4
C4 C5 H5A 109.4
O2 C5 H5B 109.4
C4 C5 H5B 109.4
H5A C5 H5B 108.0
C1 C6 C7 114.3(2)
C1 C6 H6A 108.7
C7 C6 H6A 108.7
C1 C6 H6B 108.7
C7 C6 H6B 108.7
H6A C6 H6B 107.6
C8 C7 C6 112.3(2)
C8 C7 H7A 109.1
C6 C7 H7A 109.1
C8 C7 H7B 109.1
C6 C7 H7B 109.1
H7A C7 H7B 107.9
O1 C8 C7 111.1(2)
O1 C8 H8A 109.4
C7 C8 H8A 109.4
O1 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
C14 C9 C10 118.9(2)
C14 C9 S1 116.14(18)
C10 C9 S1 124.97(19)
C11 C10 C9 119.9(2)
C11 C10 H10A 120.0
C9 C10 H10A 120.0
C12 C11 C10 120.9(2)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C13 C12 C11 119.5(2)
C13 C12 H12A 120.3
C11 C12 H12A 120.3
C12 C13 C14 120.4(2)
C12 C13 H13A 119.8
C14 C13 H13A 119.8
C13 C14 C9 120.4(2)
C13 C14 H14A 119.8
C9 C14 H14A 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.768(3)
S1 C2 1.828(3)
O1 C8 1.429(4)
O1 H1 0.8400
O2 C5 1.442(3)
O2 C1 1.442(3)
C1 C6 1.525(4)
C1 C2 1.533(3)
C1 H1A 1.0000
C2 C3 1.526(3)
C2 H2A 1.0000
C3 C4 1.523(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.506(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.529(4)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.514(4)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C14 1.395(3)
C9 C10 1.398(3)
C10 C11 1.387(4)
C10 H10A 0.9500
C11 C12 1.383(4)
C11 H11A 0.9500
C12 C13 1.381(4)
C12 H12A 0.9500
C13 C14 1.389(3)
C13 H13A 0.9500
C14 H14A 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84 1.99 2.821(3) 171.9 3_665
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 O2 C1 C6 174.1(2)
C5 O2 C1 C2 -59.5(3)
O2 C1 C2 C3 54.4(3)
C6 C1 C2 C3 175.4(2)
O2 C1 C2 S1 -69.1(2)
C6 C1 C2 S1 51.9(3)
C9 S1 C2 C3 63.5(2)
C9 S1 C2 C1 -174.65(17)
C1 C2 C3 C4 -52.1(3)
S1 C2 C3 C4 69.0(2)
C2 C3 C4 C5 53.0(3)
C1 O2 C5 C4 60.4(3)
C3 C4 C5 O2 -56.0(3)
O2 C1 C6 C7 -178.9(2)
C2 C1 C6 C7 57.7(3)
C1 C6 C7 C8 173.8(2)
C6 C7 C8 O1 63.9(3)
C2 S1 C9 C14 -160.24(19)
C2 S1 C9 C10 20.5(2)
C14 C9 C10 C11 2.3(4)
S1 C9 C10 C11 -178.51(19)
C9 C10 C11 C12 -1.4(4)
C10 C11 C12 C13 -0.7(4)
C11 C12 C13 C14 1.8(4)
C12 C13 C14 C9 -0.9(4)
C10 C9 C14 C13 -1.2(4)
S1 C9 C14 C13 179.57(19)
|
1502044.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502044.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502044
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C20 H26 O3 S'
_chemical_formula_weight 346.47
_chemical_name_systematic
;
?
;
_space_group_IT_number 43
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'F 2 -2d'
_symmetry_space_group_name_H-M 'F d d 2'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 16
_cell_length_a 25.707(5)
_cell_length_b 51.276(10)
_cell_length_c 5.6218(11)
_cell_measurement_reflns_used 5473
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.46
_cell_measurement_theta_min 2.24
_cell_volume 7410(3)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_source 'Rotating Anode'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0429
_diffrn_reflns_av_sigmaI/netI 0.0366
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_k_max 66
_diffrn_reflns_limit_k_min -59
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_number 15028
_diffrn_reflns_theta_full 27.46
_diffrn_reflns_theta_max 27.46
_diffrn_reflns_theta_min 2.24
_exptl_absorpt_coefficient_mu 0.189
_exptl_absorpt_correction_T_max 0.9906
_exptl_absorpt_correction_T_min 0.9316
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.242
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 2976
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.05
_refine_diff_density_max 0.298
_refine_diff_density_min -0.252
_refine_diff_density_rms 0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.25(11)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.082
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 265
_refine_ls_number_reflns 4198
_refine_ls_number_restraints 309
_refine_ls_restrained_S_all 1.106
_refine_ls_R_factor_all 0.0648
_refine_ls_R_factor_gt 0.0586
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+10.7601P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1345
_refine_ls_wR_factor_ref 0.1392
_reflns_number_gt 3813
_reflns_number_total 4198
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_005.cif
_cod_data_source_block a
_cod_original_sg_symbol_H-M Fdd2
_cod_database_code 1502044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.04596(4) 0.161885(13) 0.75022(15) 0.0584(2) Uani 1 1 d U . .
O1 O 0.10729(8) 0.09529(4) 0.4978(5) 0.0636(6) Uani 1 1 d U B .
O2 O 0.07300(13) 0.16180(4) 0.9731(4) 0.0840(9) Uani 1 1 d U . .
O3 O -0.00913(10) 0.15644(4) 0.7495(7) 0.0875(9) Uani 1 1 d U . .
C1 C 0.07876(11) 0.13962(5) 0.5535(5) 0.0470(6) Uani 1 1 d U B .
H1 H 0.0607 0.1398 0.3961 0.056 Uiso 1 1 calc R . .
C2 C 0.07786(13) 0.11152(5) 0.6539(6) 0.0596(8) Uani 1 1 d DU . .
H2 H 0.0928 0.1111 0.8182 0.072 Uiso 1 1 calc R A 1
C3 C 0.16019(14) 0.10272(6) 0.4820(9) 0.0766(10) Uani 1 1 d U . .
H3A H 0.1793 0.0899 0.3830 0.092 Uiso 1 1 calc R B .
H3B H 0.1759 0.1027 0.6428 0.092 Uiso 1 1 calc R . .
C4 C 0.16526(13) 0.12931(6) 0.3748(9) 0.0727(10) Uani 1 1 d U B .
H4A H 0.1522 0.1290 0.2092 0.087 Uiso 1 1 calc R . .
H4B H 0.2024 0.1344 0.3708 0.087 Uiso 1 1 calc R . .
C5 C 0.13458(11) 0.14913(5) 0.5189(7) 0.0598(8) Uani 1 1 d U . .
H5A H 0.1344 0.1661 0.4350 0.072 Uiso 1 1 calc R B .
H5B H 0.1513 0.1517 0.6758 0.072 Uiso 1 1 calc R . .
C6 C 0.05385(11) 0.19267(5) 0.6149(5) 0.0462(6) Uani 1 1 d U . .
C7 C 0.08306(11) 0.21153(5) 0.7225(5) 0.0486(6) Uani 1 1 d U . .
H7 H 0.1009 0.2078 0.8666 0.058 Uiso 1 1 calc R . .
C8 C 0.08682(11) 0.23673(5) 0.6193(5) 0.0443(6) Uani 1 1 d U . .
C9 C 0.11572(12) 0.25725(6) 0.7236(6) 0.0569(7) Uani 1 1 d U . .
H9 H 0.1340 0.2543 0.8679 0.068 Uiso 1 1 calc R . .
C10 C 0.11766(14) 0.28125(6) 0.6199(7) 0.0638(8) Uani 1 1 d U . .
H10 H 0.1366 0.2949 0.6941 0.077 Uiso 1 1 calc R . .
C11 C 0.09204(13) 0.28582(6) 0.4055(7) 0.0610(8) Uani 1 1 d U . .
H11 H 0.0943 0.3026 0.3336 0.073 Uiso 1 1 calc R . .
C12 C 0.06394(12) 0.26677(5) 0.2977(6) 0.0534(7) Uani 1 1 d U . .
H12 H 0.0465 0.2704 0.1525 0.064 Uiso 1 1 calc R . .
C13 C 0.06049(10) 0.24155(5) 0.4004(5) 0.0432(6) Uani 1 1 d U . .
C14 C 0.03092(11) 0.22136(5) 0.2950(5) 0.0461(6) Uani 1 1 d U . .
H14 H 0.0131 0.2245 0.1497 0.055 Uiso 1 1 calc R . .
C15 C 0.02755(11) 0.19743(5) 0.3987(5) 0.0468(6) Uani 1 1 d U . .
H15 H 0.0076 0.1840 0.3261 0.056 Uiso 1 1 calc R . .
C16 C 0.0243(2) 0.09814(13) 0.6483(16) 0.0704(19) Uani 0.627(6) 1 d PDU B 1
H16A H 0.0150 0.0948 0.4802 0.084 Uiso 0.627(6) 1 calc PR B 1
H16B H -0.0017 0.1105 0.7133 0.084 Uiso 0.627(6) 1 calc PR B 1
C17 C 0.0198(3) 0.07183(12) 0.7883(16) 0.0736(17) Uani 0.627(6) 1 d PDU B 1
H17A H 0.0435 0.0591 0.7127 0.088 Uiso 0.627(6) 1 calc PR B 1
H17B H 0.0327 0.0749 0.9519 0.088 Uiso 0.627(6) 1 calc PR B 1
C18 C -0.0313(3) 0.05981(11) 0.8059(14) 0.0811(18) Uani 0.627(6) 1 d PDU B 1
H18A H -0.0447 0.0574 0.6423 0.097 Uiso 0.627(6) 1 calc PR B 1
H18B H -0.0547 0.0724 0.8865 0.097 Uiso 0.627(6) 1 calc PR B 1
C19 C -0.0362(3) 0.03412(13) 0.9323(14) 0.0892(19) Uani 0.627(6) 1 d PDU B 1
H19A H -0.0122 0.0214 0.8586 0.107 Uiso 0.627(6) 1 calc PR B 1
H19B H -0.0721 0.0275 0.9134 0.107 Uiso 0.627(6) 1 calc PR B 1
C20 C -0.0238(3) 0.03648(15) 1.1945(15) 0.101(3) Uani 0.627(6) 1 d PDU B 1
H20A H 0.0118 0.0430 1.2139 0.151 Uiso 0.627(6) 1 calc PR B 1
H20B H -0.0268 0.0193 1.2700 0.151 Uiso 0.627(6) 1 calc PR B 1
H20C H -0.0482 0.0486 1.2693 0.151 Uiso 0.627(6) 1 calc PR B 1
C16' C 0.0254(4) 0.1006(2) 0.711(3) 0.074(3) Uani 0.373(6) 1 d PDU B 2
H16C H 0.0052 0.0967 0.5655 0.089 Uiso 0.373(6) 1 calc PR B 2
H16D H 0.0051 0.1126 0.8138 0.089 Uiso 0.373(6) 1 calc PR B 2
C17' C 0.0414(5) 0.0751(2) 0.847(3) 0.082(2) Uani 0.373(6) 1 d PDU B 2
H17C H 0.0620 0.0637 0.7413 0.098 Uiso 0.373(6) 1 calc PR B 2
H17D H 0.0630 0.0796 0.9872 0.098 Uiso 0.373(6) 1 calc PR B 2
C18' C -0.0050(5) 0.06170(18) 0.923(3) 0.088(2) Uani 0.373(6) 1 d PDU B 2
H18C H -0.0293 0.0615 0.7867 0.106 Uiso 0.373(6) 1 calc PR B 2
H18D H -0.0214 0.0725 1.0488 0.106 Uiso 0.373(6) 1 calc PR B 2
C19' C -0.0021(4) 0.0349(2) 1.015(3) 0.091(3) Uani 0.373(6) 1 d PDU B 2
H19C H 0.0179 0.0348 1.1652 0.110 Uiso 0.373(6) 1 calc PR B 2
H19D H 0.0164 0.0238 0.8983 0.110 Uiso 0.373(6) 1 calc PR B 2
C20' C -0.0564(4) 0.0240(2) 1.058(3) 0.096(4) Uani 0.373(6) 1 d PDU B 2
H20D H -0.0644 0.0249 1.2283 0.144 Uiso 0.373(6) 1 calc PR B 2
H20E H -0.0578 0.0059 1.0048 0.144 Uiso 0.373(6) 1 calc PR B 2
H20F H -0.0819 0.0344 0.9691 0.144 Uiso 0.373(6) 1 calc PR B 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0858(6) 0.0335(3) 0.0558(4) 0.0060(3) 0.0300(4) 0.0146(3)
O1 0.0694(13) 0.0365(9) 0.0850(16) -0.0121(11) 0.0235(13) 0.0079(8)
O2 0.162(3) 0.0439(12) 0.0463(13) 0.0081(10) 0.0155(15) 0.0344(13)
O3 0.0859(17) 0.0428(11) 0.134(2) 0.0120(15) 0.0621(18) 0.0098(10)
C1 0.0615(16) 0.0337(12) 0.0459(15) -0.0024(11) 0.0120(13) 0.0037(11)
C2 0.082(2) 0.0360(13) 0.0605(18) 0.0005(13) 0.0198(16) 0.0148(13)
C3 0.072(2) 0.0507(16) 0.107(3) -0.013(2) 0.016(2) 0.0206(15)
C4 0.0659(19) 0.0456(16) 0.107(3) -0.0137(18) 0.0299(19) 0.0058(14)
C5 0.0565(17) 0.0392(13) 0.084(2) -0.0124(16) 0.0157(17) 0.0017(11)
C6 0.0585(16) 0.0353(12) 0.0449(14) 0.0004(11) 0.0141(13) 0.0116(11)
C7 0.0651(17) 0.0397(12) 0.0410(14) 0.0031(11) 0.0040(13) 0.0122(11)
C8 0.0549(15) 0.0362(12) 0.0418(13) 0.0019(11) 0.0041(11) 0.0076(11)
C9 0.0639(18) 0.0511(15) 0.0558(18) -0.0032(14) -0.0062(15) 0.0023(13)
C10 0.072(2) 0.0446(15) 0.074(2) -0.0060(16) 0.0036(18) -0.0062(14)
C11 0.075(2) 0.0376(14) 0.070(2) 0.0061(14) 0.0145(17) 0.0022(13)
C12 0.0612(17) 0.0459(14) 0.0531(17) 0.0083(13) 0.0038(14) 0.0112(12)
C13 0.0459(14) 0.0390(12) 0.0447(14) -0.0004(11) 0.0070(12) 0.0061(10)
C14 0.0536(15) 0.0423(13) 0.0425(15) -0.0006(11) 0.0008(12) 0.0088(11)
C15 0.0535(15) 0.0380(12) 0.0489(15) -0.0066(12) 0.0070(13) 0.0027(11)
C16 0.087(3) 0.039(3) 0.085(4) -0.009(3) 0.039(3) 0.005(2)
C17 0.076(3) 0.042(2) 0.103(4) 0.002(3) 0.023(3) -0.002(2)
C18 0.096(4) 0.051(3) 0.096(4) 0.007(3) 0.007(3) -0.015(3)
C19 0.103(4) 0.057(3) 0.108(4) 0.013(3) -0.002(4) -0.003(3)
C20 0.107(5) 0.076(4) 0.120(6) 0.018(4) 0.018(4) 0.013(4)
C16' 0.093(4) 0.045(4) 0.086(5) 0.002(4) 0.043(4) 0.005(3)
C17' 0.096(5) 0.054(4) 0.095(5) 0.003(4) 0.027(4) -0.003(4)
C18' 0.099(4) 0.062(4) 0.104(5) 0.004(4) 0.015(4) 0.003(4)
C19' 0.105(5) 0.061(4) 0.108(5) 0.015(5) 0.004(5) 0.007(4)
C20' 0.090(6) 0.084(6) 0.115(7) -0.001(6) 0.007(6) -0.008(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 118.5(2)
O2 S1 C6 108.91(15)
O3 S1 C6 106.53(14)
O2 S1 C1 107.95(14)
O3 S1 C1 109.59(16)
C6 S1 C1 104.42(13)
C3 O1 C2 113.0(3)
C5 C1 C2 110.9(2)
C5 C1 S1 108.42(19)
C2 C1 S1 111.08(19)
C5 C1 H1 108.8
C2 C1 H1 108.8
S1 C1 H1 108.8
O1 C2 C16' 113.2(7)
O1 C2 C16 101.6(4)
C16' C2 C16 14.2(9)
O1 C2 C1 108.1(2)
C16' C2 C1 116.0(5)
C16 C2 C1 114.9(4)
O1 C2 H2 110.6
C16' C2 H2 98.0
C16 C2 H2 110.6
C1 C2 H2 110.6
O1 C3 C4 110.8(3)
O1 C3 H3A 109.5
C4 C3 H3A 109.5
O1 C3 H3B 109.5
C4 C3 H3B 109.5
H3A C3 H3B 108.1
C3 C4 C5 110.5(3)
C3 C4 H4A 109.6
C5 C4 H4A 109.6
C3 C4 H4B 109.6
C5 C4 H4B 109.6
H4A C4 H4B 108.1
C4 C5 C1 110.0(2)
C4 C5 H5A 109.7
C1 C5 H5A 109.7
C4 C5 H5B 109.7
C1 C5 H5B 109.7
H5A C5 H5B 108.2
C7 C6 C15 121.5(3)
C7 C6 S1 120.4(2)
C15 C6 S1 118.1(2)
C6 C7 C8 120.0(3)
C6 C7 H7 120.0
C8 C7 H7 120.0
C9 C8 C7 122.9(3)
C9 C8 C13 118.6(3)
C7 C8 C13 118.6(3)
C10 C9 C8 120.9(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 120.3(3)
C9 C10 H10 119.8
C11 C10 H10 119.8
C12 C11 C10 121.1(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 120.5(3)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 122.0(3)
C14 C13 C8 119.3(2)
C12 C13 C8 118.6(3)
C15 C14 C13 120.9(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C14 C15 C6 119.6(3)
C14 C15 H15 120.2
C6 C15 H15 120.2
C2 C16 C17 116.1(5)
C2 C16 H16A 108.3
C17 C16 H16A 108.3
C2 C16 H16B 108.3
C17 C16 H16B 108.3
H16A C16 H16B 107.4
C18 C17 C16 117.8(6)
C18 C17 H17A 107.9
C16 C17 H17A 107.9
C18 C17 H17B 107.9
C16 C17 H17B 107.9
H17A C17 H17B 107.2
C17 C18 C19 118.7(6)
C17 C18 H18A 107.6
C19 C18 H18A 107.6
C17 C18 H18B 107.6
C19 C18 H18B 107.6
H18A C18 H18B 107.1
C18 C19 C20 111.9(6)
C18 C19 H19A 109.2
C20 C19 H19A 109.2
C18 C19 H19B 109.2
C20 C19 H19B 109.2
H19A C19 H19B 107.9
C2 C16' C17' 100.3(7)
C2 C16' H16C 111.7
C17' C16' H16C 111.7
C2 C16' H16D 111.7
C17' C16' H16D 111.7
H16C C16' H16D 109.5
C18' C17' C16' 109.0(9)
C18' C17' H17C 109.9
C16' C17' H17C 109.9
C18' C17' H17D 109.9
C16' C17' H17D 109.9
H17C C17' H17D 108.3
C17' C18' C19' 120.5(9)
C17' C18' H18C 107.2
C19' C18' H18C 107.2
C17' C18' H18D 107.2
C19' C18' H18D 107.2
H18C C18' H18D 106.8
C18' C19' C20' 110.6(9)
C18' C19' H19C 109.5
C20' C19' H19C 109.5
C18' C19' H19D 109.5
C20' C19' H19D 109.5
H19C C19' H19D 108.1
C19' C20' H20D 109.5
C19' C20' H20E 109.5
H20D C20' H20E 109.5
C19' C20' H20F 109.5
H20D C20' H20F 109.5
H20E C20' H20F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.433(3)
S1 O3 1.444(3)
S1 C6 1.764(3)
S1 C1 1.799(3)
O1 C3 1.415(4)
O1 C2 1.427(3)
C1 C5 1.528(4)
C1 C2 1.548(4)
C1 H1 1.0000
C2 C16' 1.495(8)
C2 C16 1.539(6)
C2 H2 1.0000
C3 C4 1.496(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.520(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.366(4)
C6 C15 1.412(4)
C7 C8 1.420(3)
C7 H7 0.9500
C8 C9 1.415(4)
C8 C13 1.426(4)
C9 C10 1.363(4)
C9 H9 0.9500
C10 C11 1.393(5)
C10 H10 0.9500
C11 C12 1.358(5)
C11 H11 0.9500
C12 C13 1.419(4)
C12 H12 0.9500
C13 C14 1.415(4)
C14 C15 1.361(4)
C14 H14 0.9500
C15 H15 0.9500
C16 C17 1.567(7)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.454(8)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.502(7)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.513(9)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C16' C17' 1.572(9)
C16' H16C 0.9900
C16' H16D 0.9900
C17' C18' 1.441(10)
C17' H17C 0.9900
C17' H17D 0.9900
C18' C19' 1.467(10)
C18' H18C 0.9900
C18' H18D 0.9900
C19' C20' 1.524(10)
C19' H19C 0.9900
C19' H19D 0.9900
C20' H20D 0.9800
C20' H20E 0.9800
C20' H20F 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 C1 C5 -60.8(3)
O3 S1 C1 C5 168.8(2)
C6 S1 C1 C5 55.0(2)
O2 S1 C1 C2 61.4(3)
O3 S1 C1 C2 -69.1(3)
C6 S1 C1 C2 177.2(2)
C3 O1 C2 C16' -167.9(7)
C3 O1 C2 C16 -176.6(4)
C3 O1 C2 C1 62.1(4)
C5 C1 C2 O1 -55.6(3)
S1 C1 C2 O1 -176.3(2)
C5 C1 C2 C16' 176.0(8)
S1 C1 C2 C16' 55.4(9)
C5 C1 C2 C16 -168.3(4)
S1 C1 C2 C16 71.0(5)
C2 O1 C3 C4 -64.1(5)
O1 C3 C4 C5 57.1(5)
C3 C4 C5 C1 -51.9(4)
C2 C1 C5 C4 51.8(4)
S1 C1 C5 C4 174.0(3)
O2 S1 C6 C7 1.3(3)
O3 S1 C6 C7 130.2(3)
C1 S1 C6 C7 -113.9(2)
O2 S1 C6 C15 -176.3(2)
O3 S1 C6 C15 -47.4(3)
C1 S1 C6 C15 68.6(2)
C15 C6 C7 C8 1.1(4)
S1 C6 C7 C8 -176.4(2)
C6 C7 C8 C9 178.9(3)
C6 C7 C8 C13 -1.3(4)
C7 C8 C9 C10 -179.1(3)
C13 C8 C9 C10 1.2(4)
C8 C9 C10 C11 -1.4(5)
C9 C10 C11 C12 1.2(5)
C10 C11 C12 C13 -0.7(5)
C11 C12 C13 C14 179.0(3)
C11 C12 C13 C8 0.4(4)
C9 C8 C13 C14 -179.3(3)
C7 C8 C13 C14 1.0(4)
C9 C8 C13 C12 -0.6(4)
C7 C8 C13 C12 179.6(3)
C12 C13 C14 C15 -179.0(3)
C8 C13 C14 C15 -0.4(4)
C13 C14 C15 C6 0.1(4)
C7 C6 C15 C14 -0.5(4)
S1 C6 C15 C14 177.1(2)
O1 C2 C16 C17 74.0(7)
C16' C2 C16 C17 -72(3)
C1 C2 C16 C17 -169.6(5)
C2 C16 C17 C18 174.4(7)
C16 C17 C18 C19 178.0(7)
C17 C18 C19 C20 65.5(10)
O1 C2 C16' C17' 64.0(11)
C16 C2 C16' C17' 101(3)
C1 C2 C16' C17' -170.1(7)
C2 C16' C17' C18' 178.9(12)
C16' C17' C18' C19' 168.4(14)
C17' C18' C19' C20' -174.0(14)
|
1502045.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502045
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C20 H26 O3 S'
_chemical_formula_weight 346.47
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 98.79(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.8790(16)
_cell_length_b 20.374(4)
_cell_length_c 11.622(2)
_cell_measurement_reflns_used 4645
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 25.00
_cell_measurement_theta_min 2.00
_cell_volume 1843.7(6)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_source 'Rotating Anode'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0505
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 3365
_diffrn_reflns_theta_full 25.49
_diffrn_reflns_theta_max 25.49
_diffrn_reflns_theta_min 2.00
_exptl_absorpt_coefficient_mu 0.190
_exptl_absorpt_correction_T_max 0.9943
_exptl_absorpt_correction_T_min 0.9612
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.248
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 744
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.430
_refine_diff_density_min -0.372
_refine_diff_density_rms 0.064
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.169
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 238
_refine_ls_number_reflns 3365
_refine_ls_number_restraints 40
_refine_ls_restrained_S_all 1.169
_refine_ls_R_factor_all 0.0894
_refine_ls_R_factor_gt 0.0790
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+1.4694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1657
_refine_ls_wR_factor_ref 0.1720
_reflns_number_gt 2994
_reflns_number_total 3365
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_006.cif
_cod_data_source_block mx337
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20383(12) 0.28982(4) 0.83405(8) 0.0303(3) Uani 1 1 d . . .
O1 O 0.5022(8) 0.2532(4) 1.0307(8) 0.044(2) Uani 0.559(15) 1 d PDU A 1
C3 C 0.7904(11) 0.2513(4) 0.9957(10) 0.054(3) Uani 0.559(15) 1 d PDU A 1
H3A H 0.9054 0.2545 1.0434 0.064 Uiso 0.559(15) 1 calc PR A 1
H3B H 0.7994 0.2242 0.9262 0.064 Uiso 0.559(15) 1 calc PR A 1
O1' O 0.5133(11) 0.2402(4) 0.9888(10) 0.046(3) Uani 0.441(15) 1 d PDU A 2
C3' C 0.8014(12) 0.2741(6) 1.0546(12) 0.058(3) Uani 0.441(15) 1 d PDU A 2
H3'A H 0.8298 0.2989 1.1283 0.070 Uiso 0.441(15) 1 calc PR A 2
H3'B H 0.9076 0.2537 1.0353 0.070 Uiso 0.441(15) 1 calc PR A 2
O2 O 0.1142(3) 0.30986(12) 0.7219(2) 0.0372(6) Uani 1 1 d . . .
O3 O 0.1500(3) 0.31760(12) 0.9370(2) 0.0376(6) Uani 1 1 d . . .
C1 C 0.5283(5) 0.3088(2) 0.9580(4) 0.0533(12) Uani 1 1 d D . .
H1 H 0.4883 0.3485 0.9969 0.064 Uiso 1 1 calc R A 1
C2 C 0.7242(5) 0.3169(2) 0.9610(5) 0.0683(16) Uani 1 1 d D A .
H2A H 0.7516 0.3292 0.8834 0.082 Uiso 1 1 calc R B 1
H2B H 0.7718 0.3505 1.0185 0.082 Uiso 1 1 calc R B 1
C4 C 0.6643(6) 0.2216(2) 1.0651(4) 0.0543(12) Uani 1 1 d D . .
H4A H 0.6537 0.1738 1.0499 0.065 Uiso 1 1 calc R A 1
H4B H 0.7035 0.2282 1.1494 0.065 Uiso 1 1 calc R A 1
C5 C 0.4298(5) 0.30775(18) 0.8352(4) 0.0383(9) Uani 1 1 d . A .
H5A H 0.4787 0.2716 0.7923 0.046 Uiso 1 1 calc R . .
C6 C 0.4469(5) 0.37198(18) 0.7675(4) 0.0402(9) Uani 1 1 d . . .
H6A H 0.5682 0.3765 0.7558 0.048 Uiso 1 1 calc R A .
H6B H 0.3769 0.3676 0.6895 0.048 Uiso 1 1 calc R . .
C7 C 0.3938(5) 0.43537(18) 0.8227(4) 0.0416(9) Uani 1 1 d . A .
H7A H 0.4743 0.4442 0.8951 0.050 Uiso 1 1 calc R . .
H7B H 0.2775 0.4299 0.8436 0.050 Uiso 1 1 calc R . .
C8 C 0.3937(5) 0.49398(18) 0.7401(4) 0.0416(9) Uani 1 1 d . . .
H8A H 0.5077 0.4969 0.7146 0.050 Uiso 1 1 calc R A .
H8B H 0.3077 0.4859 0.6701 0.050 Uiso 1 1 calc R . .
C9 C 0.3548(7) 0.5584(2) 0.7917(5) 0.0599(13) Uani 1 1 d . A .
H9A H 0.4450 0.5682 0.8586 0.072 Uiso 1 1 calc R . .
H9B H 0.2439 0.5550 0.8216 0.072 Uiso 1 1 calc R . .
C10 C 0.3447(7) 0.6151(2) 0.7044(5) 0.0706(15) Uani 1 1 d . . .
H10A H 0.3228 0.6562 0.7433 0.106 Uiso 1 1 calc R A .
H10B H 0.2513 0.6069 0.6401 0.106 Uiso 1 1 calc R . .
H10C H 0.4537 0.6185 0.6738 0.106 Uiso 1 1 calc R . .
C11 C 0.1863(4) 0.20327(17) 0.8414(3) 0.0306(8) Uani 1 1 d . . .
C12 C 0.1776(5) 0.16721(17) 0.7400(3) 0.0319(8) Uani 1 1 d . . .
H12A H 0.1857 0.1885 0.6683 0.038 Uiso 1 1 calc R . .
C13 C 0.1565(5) 0.09797(17) 0.7436(3) 0.0327(8) Uani 1 1 d . . .
C14 C 0.1454(5) 0.05880(19) 0.6416(3) 0.0419(10) Uani 1 1 d . . .
H14A H 0.1543 0.0788 0.5689 0.050 Uiso 1 1 calc R . .
C15 C 0.1218(5) -0.00782(19) 0.6473(4) 0.0450(10) Uani 1 1 d . . .
H15A H 0.1131 -0.0335 0.5784 0.054 Uiso 1 1 calc R . .
C16 C 0.1104(5) -0.03850(19) 0.7551(4) 0.0460(10) Uani 1 1 d . . .
H16A H 0.0939 -0.0846 0.7584 0.055 Uiso 1 1 calc R . .
C17 C 0.1232(5) -0.00193(18) 0.8539(4) 0.0411(9) Uani 1 1 d . . .
H17A H 0.1169 -0.0231 0.9259 0.049 Uiso 1 1 calc R . .
C18 C 0.1455(5) 0.06706(17) 0.8520(3) 0.0339(8) Uani 1 1 d . . .
C19 C 0.1563(5) 0.10667(19) 0.9536(3) 0.0382(9) Uani 1 1 d . . .
H19A H 0.1490 0.0865 1.0263 0.046 Uiso 1 1 calc R . .
C20 C 0.1767(5) 0.17300(19) 0.9489(3) 0.0354(8) Uani 1 1 d . . .
H20A H 0.1843 0.1986 1.0178 0.042 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0344(5) 0.0318(5) 0.0250(4) -0.0028(4) 0.0059(4) 0.0011(4)
O1 0.039(3) 0.053(3) 0.035(4) 0.012(3) -0.009(3) -0.010(3)
C3 0.051(4) 0.066(5) 0.049(5) 0.008(4) 0.022(4) 0.005(4)
O1' 0.044(4) 0.050(4) 0.041(5) 0.011(4) -0.004(4) -0.012(3)
C3' 0.050(5) 0.077(6) 0.050(6) 0.018(5) 0.016(5) 0.006(5)
O2 0.0491(16) 0.0332(13) 0.0268(13) 0.0013(11) -0.0022(12) 0.0024(11)
O3 0.0457(16) 0.0415(14) 0.0282(13) -0.0111(11) 0.0140(12) 0.0002(12)
C1 0.037(2) 0.049(2) 0.071(3) 0.023(2) -0.001(2) -0.0052(19)
C2 0.033(2) 0.068(3) 0.098(4) 0.029(3) -0.006(3) -0.009(2)
C4 0.057(3) 0.054(3) 0.050(3) 0.013(2) 0.001(2) 0.002(2)
C5 0.035(2) 0.035(2) 0.047(2) -0.0022(18) 0.0102(18) 0.0035(16)
C6 0.040(2) 0.036(2) 0.046(2) 0.0010(18) 0.0113(19) -0.0005(17)
C7 0.047(2) 0.035(2) 0.042(2) -0.0022(18) 0.0073(19) -0.0006(17)
C8 0.043(2) 0.036(2) 0.046(2) 0.0021(18) 0.0051(19) -0.0020(17)
C9 0.067(3) 0.042(2) 0.070(3) -0.003(2) 0.007(3) 0.003(2)
C10 0.073(3) 0.037(2) 0.097(4) 0.011(3) -0.002(3) 0.000(2)
C11 0.0289(19) 0.0348(19) 0.0279(18) -0.0028(15) 0.0041(15) -0.0004(15)
C12 0.037(2) 0.0347(18) 0.0224(17) 0.0060(15) 0.0010(16) 0.0007(16)
C13 0.034(2) 0.0336(19) 0.0303(19) 0.0019(15) 0.0050(16) 0.0004(15)
C14 0.054(3) 0.038(2) 0.033(2) -0.0014(17) 0.0031(19) 0.0024(18)
C15 0.051(3) 0.038(2) 0.043(2) -0.0072(18) -0.003(2) -0.0009(19)
C16 0.045(2) 0.030(2) 0.062(3) 0.0052(19) 0.004(2) -0.0025(17)
C17 0.040(2) 0.035(2) 0.048(2) 0.0081(18) 0.0075(19) -0.0024(17)
C18 0.031(2) 0.0341(19) 0.036(2) 0.0071(16) 0.0032(16) -0.0018(16)
C19 0.044(2) 0.045(2) 0.0265(19) 0.0031(16) 0.0064(17) -0.0054(18)
C20 0.037(2) 0.043(2) 0.0256(19) -0.0006(16) 0.0014(16) -0.0007(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 118.17(15)
O2 S1 C11 107.11(16)
O3 S1 C11 108.37(16)
O2 S1 C5 107.09(18)
O3 S1 C5 109.05(17)
C11 S1 C5 106.46(17)
C4 O1 C1 108.4(5)
C2 C3 C4 106.2(5)
C2 C3 H3A 110.5
C4 C3 H3A 110.5
C2 C3 H3B 110.5
C4 C3 H3B 110.5
H3A C3 H3B 108.7
C4 O1' C1 108.6(5)
C2 C3' C4 105.0(6)
C2 C3' H3'A 110.7
C4 C3' H3'A 110.7
C2 C3' H3'B 110.7
C4 C3' H3'B 110.7
H3'A C3' H3'B 108.8
O1 C1 O1' 22.8(5)
O1 C1 C5 116.1(5)
O1' C1 C5 99.7(5)
O1 C1 C2 107.5(4)
O1' C1 C2 102.4(5)
C5 C1 C2 112.8(4)
O1 C1 H1 106.6
O1' C1 H1 128.5
C5 C1 H1 106.6
C2 C1 H1 106.6
C3' C2 C3 32.6(5)
C3' C2 C1 104.7(5)
C3 C2 C1 102.7(5)
C3' C2 H2A 135.1
C3 C2 H2A 111.2
C1 C2 H2A 111.2
C3' C2 H2B 80.7
C3 C2 H2B 111.2
C1 C2 H2B 111.2
H2A C2 H2B 109.1
O1' C4 O1 23.1(5)
O1' C4 C3 96.7(6)
O1 C4 C3 107.7(5)
O1' C4 C3' 107.2(5)
O1 C4 C3' 105.8(5)
C3 C4 C3' 31.3(5)
O1' C4 H4A 96.4
O1 C4 H4A 110.2
C3 C4 H4A 110.2
C3' C4 H4A 135.2
O1' C4 H4B 133.2
O1 C4 H4B 110.2
C3 C4 H4B 110.2
C3' C4 H4B 82.4
H4A C4 H4B 108.5
C1 C5 C6 113.3(3)
C1 C5 S1 111.7(3)
C6 C5 S1 109.2(3)
C1 C5 H5A 107.5
C6 C5 H5A 107.5
S1 C5 H5A 107.5
C7 C6 C5 116.8(3)
C7 C6 H6A 108.1
C5 C6 H6A 108.1
C7 C6 H6B 108.1
C5 C6 H6B 108.1
H6A C6 H6B 107.3
C6 C7 C8 111.7(3)
C6 C7 H7A 109.3
C8 C7 H7A 109.3
C6 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 107.9
C9 C8 C7 114.4(4)
C9 C8 H8A 108.7
C7 C8 H8A 108.7
C9 C8 H8B 108.7
C7 C8 H8B 108.7
H8A C8 H8B 107.6
C8 C9 C10 112.9(4)
C8 C9 H9A 109.0
C10 C9 H9A 109.0
C8 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C20 121.5(3)
C12 C11 S1 118.8(3)
C20 C11 S1 119.7(3)
C11 C12 C13 119.5(3)
C11 C12 H12A 120.2
C13 C12 H12A 120.2
C14 C13 C12 121.7(3)
C14 C13 C18 119.1(3)
C12 C13 C18 119.3(3)
C15 C14 C13 120.4(4)
C15 C14 H14A 119.8
C13 C14 H14A 119.8
C14 C15 C16 120.5(4)
C14 C15 H15A 119.8
C16 C15 H15A 119.8
C17 C16 C15 119.9(4)
C17 C16 H16A 120.0
C15 C16 H16A 120.0
C16 C17 C18 121.6(4)
C16 C17 H17A 119.2
C18 C17 H17A 119.2
C17 C18 C19 122.8(3)
C17 C18 C13 118.5(3)
C19 C18 C13 118.7(3)
C20 C19 C18 121.5(3)
C20 C19 H19A 119.3
C18 C19 H19A 119.3
C19 C20 C11 119.6(3)
C19 C20 H20A 120.2
C11 C20 H20A 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.443(3)
S1 O3 1.444(2)
S1 C11 1.772(4)
S1 C5 1.815(4)
O1 C4 1.432(7)
O1 C1 1.448(6)
C3 C2 1.469(8)
C3 C4 1.501(8)
C3 H3A 0.9900
C3 H3B 0.9900
O1' C4 1.422(7)
O1' C1 1.453(7)
C3' C2 1.454(9)
C3' C4 1.539(9)
C3' H3'A 0.9900
C3' H3'B 0.9900
C1 C5 1.516(6)
C1 C2 1.548(6)
C1 H1 1.0000
C2 H2A 0.9900
C2 H2B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.544(5)
C5 H5A 1.0000
C6 C7 1.528(5)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.532(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.494(6)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.532(6)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.382(5)
C11 C20 1.405(5)
C12 C13 1.422(5)
C12 H12A 0.9500
C13 C14 1.421(5)
C13 C18 1.423(5)
C14 C15 1.373(5)
C14 H14A 0.9500
C15 C16 1.415(6)
C15 H15A 0.9500
C16 C17 1.360(6)
C16 H16A 0.9500
C17 C18 1.417(5)
C17 H17A 0.9500
C18 C19 1.421(5)
C19 C20 1.363(5)
C19 H19A 0.9500
C20 H20A 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O1 C1 O1' 72.7(11)
C4 O1 C1 C5 119.8(6)
C4 O1 C1 C2 -7.6(9)
C4 O1' C1 O1 -74.4(10)
C4 O1' C1 C5 147.5(8)
C4 O1' C1 C2 31.4(10)
C4 C3' C2 C3 -65.9(7)
C4 C3' C2 C1 24.7(11)
C4 C3 C2 C3' 70.3(7)
C4 C3 C2 C1 -27.2(9)
O1 C1 C2 C3' -11.6(11)
O1' C1 C2 C3' -34.6(11)
C5 C1 C2 C3' -140.9(8)
O1 C1 C2 C3 21.9(9)
O1' C1 C2 C3 -1.1(10)
C5 C1 C2 C3 -107.4(6)
C1 O1' C4 O1 73.5(10)
C1 O1' C4 C3 -46.8(8)
C1 O1' C4 C3' -16.7(10)
C1 O1 C4 O1' -73.9(10)
C1 O1 C4 C3 -9.7(8)
C1 O1 C4 C3' 22.9(8)
C2 C3 C4 O1' 45.0(8)
C2 C3 C4 O1 24.1(9)
C2 C3 C4 C3' -67.3(7)
C2 C3' C4 O1' -6.1(11)
C2 C3' C4 O1 -30.2(10)
C2 C3' C4 C3 68.0(7)
O1 C1 C5 C6 173.3(5)
O1' C1 C5 C6 -170.0(6)
C2 C1 C5 C6 -62.1(5)
O1 C1 C5 S1 49.4(5)
O1' C1 C5 S1 66.1(6)
C2 C1 C5 S1 174.1(3)
O2 S1 C5 C1 162.3(3)
O3 S1 C5 C1 33.4(3)
C11 S1 C5 C1 -83.3(3)
O2 S1 C5 C6 36.2(3)
O3 S1 C5 C6 -92.7(3)
C11 S1 C5 C6 150.5(3)
C1 C5 C6 C7 -56.5(5)
S1 C5 C6 C7 68.7(4)
C5 C6 C7 C8 -172.3(3)
C6 C7 C8 C9 -176.0(4)
C7 C8 C9 C10 -176.4(4)
O2 S1 C11 C12 31.3(3)
O3 S1 C11 C12 159.8(3)
C5 S1 C11 C12 -83.0(3)
O2 S1 C11 C20 -146.9(3)
O3 S1 C11 C20 -18.4(3)
C5 S1 C11 C20 98.8(3)
C20 C11 C12 C13 0.7(5)
S1 C11 C12 C13 -177.5(3)
C11 C12 C13 C14 179.4(3)
C11 C12 C13 C18 -0.3(5)
C12 C13 C14 C15 -178.8(4)
C18 C13 C14 C15 1.0(6)
C13 C14 C15 C16 -0.8(6)
C14 C15 C16 C17 -0.1(6)
C15 C16 C17 C18 0.9(6)
C16 C17 C18 C19 178.9(4)
C16 C17 C18 C13 -0.7(6)
C14 C13 C18 C17 -0.2(5)
C12 C13 C18 C17 179.5(3)
C14 C13 C18 C19 -179.8(4)
C12 C13 C18 C19 -0.1(5)
C17 C18 C19 C20 -179.6(4)
C13 C18 C19 C20 0.0(6)
C18 C19 C20 C11 0.4(6)
C12 C11 C20 C19 -0.8(6)
S1 C11 C20 C19 177.4(3)
|
1502046.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502046.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502046
loop_
_publ_author_name
'Wang, Haining'
'Huang, Deshun'
'Cheng, Donghao'
'Li, Lijun'
'Shi, Yian'
_publ_section_title
;
Acid-catalyzed regioselective sulfetherification of alkenols and
stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1650
_journal_page_last 1653
_journal_paper_doi 10.1021/ol200127n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C20 H26 O3 S'
_chemical_formula_weight 346.47
_chemical_name_systematic
;
?
;
_space_group_IT_number 43
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'F 2 -2d'
_symmetry_space_group_name_H-M 'F d d 2'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 16
_cell_length_a 23.497(5)
_cell_length_b 52.752(11)
_cell_length_c 5.7732(12)
_cell_measurement_reflns_used 4753
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 27.47
_cell_measurement_theta_min 1.90
_cell_volume 7156(3)
_computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection 'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator Confocal
_diffrn_radiation_source 'Rotating Anode'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0635
_diffrn_reflns_av_sigmaI/netI 0.0530
_diffrn_reflns_limit_h_max 30
_diffrn_reflns_limit_h_min -30
_diffrn_reflns_limit_k_max 68
_diffrn_reflns_limit_k_min -68
_diffrn_reflns_limit_l_max 5
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_number 13434
_diffrn_reflns_theta_full 27.47
_diffrn_reflns_theta_max 27.47
_diffrn_reflns_theta_min 1.90
_exptl_absorpt_coefficient_mu 0.196
_exptl_absorpt_correction_T_max 0.9941
_exptl_absorpt_correction_T_min 0.9600
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.286
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 2976
_exptl_crystal_size_max 0.21
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.391
_refine_diff_density_min -0.411
_refine_diff_density_rms 0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.01(13)
_refine_ls_extinction_coef 0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method SHELXL
_refine_ls_goodness_of_fit_ref 1.168
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 219
_refine_ls_number_reflns 3498
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.168
_refine_ls_R_factor_all 0.0737
_refine_ls_R_factor_gt 0.0679
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+10.9651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1658
_refine_ls_wR_factor_ref 0.1705
_reflns_number_gt 3191
_reflns_number_total 3498
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200127n_si_007.cif
_cod_data_source_block a
_cod_original_sg_symbol_H-M Fdd2
_cod_database_code 1502046
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.21003(5) 0.086894(17) 0.06942(17) 0.0422(3) Uani 1 1 d .
O1 O 0.16180(12) 0.15132(5) 0.3806(5) 0.0440(7) Uani 1 1 d .
O2 O 0.18475(16) 0.08632(5) -0.1564(6) 0.0620(9) Uani 1 1 d .
O3 O 0.26953(12) 0.09307(5) 0.0914(8) 0.0618(10) Uani 1 1 d .
C1 C 0.17143(16) 0.10806(6) 0.2508(7) 0.0375(9) Uani 1 1 d .
H1A H 0.1808 0.1034 0.4142 0.045 Uiso 1 1 calc R
C2 C 0.19142(16) 0.13577(7) 0.2166(7) 0.0374(8) Uani 1 1 d .
H2A H 0.2327 0.1363 0.2589 0.045 Uiso 1 1 calc R
C3 C 0.10118(17) 0.15026(7) 0.3541(9) 0.0499(11) Uani 1 1 d .
H3A H 0.0907 0.1558 0.1960 0.060 Uiso 1 1 calc R
H3B H 0.0831 0.1620 0.4660 0.060 Uiso 1 1 calc R
C4 C 0.07945(18) 0.12382(8) 0.3941(8) 0.0473(10) Uani 1 1 d .
H4A H 0.0377 0.1235 0.3725 0.057 Uiso 1 1 calc R
H4B H 0.0879 0.1186 0.5552 0.057 Uiso 1 1 calc R
C5 C 0.10746(16) 0.10534(7) 0.2254(8) 0.0433(9) Uani 1 1 d .
H5A H 0.0957 0.0878 0.2613 0.052 Uiso 1 1 calc R
H5B H 0.0958 0.1093 0.0646 0.052 Uiso 1 1 calc R
C6 C 0.19894(16) 0.05699(7) 0.2001(7) 0.0373(8) Uani 1 1 d .
C7 C 0.16755(16) 0.03881(7) 0.0892(7) 0.0389(8) Uani 1 1 d .
H7A H 0.1500 0.0425 -0.0552 0.047 Uiso 1 1 calc R
C8 C 0.16126(15) 0.01452(7) 0.1901(7) 0.0353(8) Uani 1 1 d .
C9 C 0.12970(16) -0.00516(7) 0.0819(8) 0.0409(9) Uani 1 1 d .
H9A H 0.1117 -0.0021 -0.0629 0.049 Uiso 1 1 calc R
C10 C 0.12490(17) -0.02845(8) 0.1835(8) 0.0463(10) Uani 1 1 d .
H10A H 0.1033 -0.0414 0.1102 0.056 Uiso 1 1 calc R
C11 C 0.15171(17) -0.03330(7) 0.3951(8) 0.0435(9) Uani 1 1 d .
H11A H 0.1487 -0.0497 0.4627 0.052 Uiso 1 1 calc R
C12 C 0.18216(16) -0.01494(6) 0.5061(7) 0.0375(8) Uani 1 1 d .
H12A H 0.1998 -0.0185 0.6506 0.045 Uiso 1 1 calc R
C13 C 0.18752(14) 0.00956(6) 0.4055(6) 0.0323(8) Uani 1 1 d .
C14 C 0.21956(15) 0.02883(7) 0.5137(7) 0.0360(8) Uani 1 1 d .
H14A H 0.2375 0.0255 0.6580 0.043 Uiso 1 1 calc R
C15 C 0.22517(16) 0.05206(7) 0.4148(7) 0.0382(8) Uani 1 1 d .
H15A H 0.2467 0.0649 0.4900 0.046 Uiso 1 1 calc R
C16 C 0.18651(17) 0.14557(7) -0.0303(8) 0.0406(9) Uani 1 1 d .
H16A H 0.1475 0.1422 -0.0876 0.049 Uiso 1 1 calc R
H16B H 0.2133 0.1360 -0.1297 0.049 Uiso 1 1 calc R
C17 C 0.19893(17) 0.17391(7) -0.0545(8) 0.0433(9) Uani 1 1 d .
H17A H 0.2003 0.1781 -0.2215 0.052 Uiso 1 1 calc R
H17B H 0.1668 0.1835 0.0141 0.052 Uiso 1 1 calc R
C18 C 0.2535(2) 0.18289(8) 0.0571(12) 0.0628(13) Uani 1 1 d .
H18A H 0.2855 0.1723 0.0004 0.075 Uiso 1 1 calc R
H18B H 0.2507 0.1805 0.2268 0.075 Uiso 1 1 calc R
C19 C 0.2666(2) 0.21115(10) 0.0053(14) 0.0803(19) Uani 1 1 d .
H19A H 0.2312 0.2211 0.0229 0.096 Uiso 1 1 calc R
H19B H 0.2943 0.2175 0.1205 0.096 Uiso 1 1 calc R
C20 C 0.2895(3) 0.21522(13) -0.2277(15) 0.108(3) Uani 1 1 d .
H20A H 0.3018 0.2329 -0.2435 0.161 Uiso 1 1 calc R
H20B H 0.2599 0.2116 -0.3428 0.161 Uiso 1 1 calc R
H20C H 0.3220 0.2039 -0.2527 0.161 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0574(6) 0.0316(4) 0.0378(5) 0.0047(4) 0.0176(5) 0.0063(4)
O1 0.0601(17) 0.0386(14) 0.0332(15) -0.0087(11) 0.0041(13) -0.0047(12)
O2 0.115(3) 0.0382(15) 0.0331(17) 0.0034(13) 0.0080(18) 0.0140(15)
O3 0.0477(16) 0.0461(16) 0.092(3) 0.0189(19) 0.0295(19) 0.0057(12)
C1 0.0456(19) 0.0291(16) 0.038(2) 0.0013(15) 0.0047(17) 0.0004(15)
C2 0.0403(19) 0.0371(18) 0.035(2) 0.0004(16) 0.0023(16) 0.0044(15)
C3 0.056(2) 0.045(2) 0.049(3) -0.010(2) 0.021(2) 0.0095(18)
C4 0.048(2) 0.046(2) 0.048(3) -0.0060(19) 0.0135(19) -0.0016(17)
C5 0.045(2) 0.043(2) 0.041(2) -0.0056(18) 0.0034(18) -0.0062(17)
C6 0.0443(19) 0.0337(17) 0.034(2) -0.0004(16) 0.0080(17) 0.0062(14)
C7 0.0470(19) 0.0413(19) 0.028(2) -0.0017(16) 0.0050(17) 0.0111(16)
C8 0.0382(18) 0.0348(17) 0.033(2) 0.0012(15) 0.0030(16) 0.0041(14)
C9 0.0432(19) 0.043(2) 0.036(2) -0.0051(18) -0.0059(19) 0.0032(15)
C10 0.046(2) 0.041(2) 0.052(3) -0.0069(19) -0.001(2) -0.0064(17)
C11 0.050(2) 0.0327(18) 0.048(3) 0.0044(17) 0.0101(19) -0.0038(16)
C12 0.0437(19) 0.0346(18) 0.034(2) 0.0055(15) 0.0030(16) 0.0046(15)
C13 0.0358(17) 0.0311(16) 0.030(2) 0.0006(14) 0.0066(15) 0.0021(13)
C14 0.0430(19) 0.0350(17) 0.030(2) -0.0015(14) 0.0018(15) 0.0010(15)
C15 0.0431(19) 0.0344(18) 0.037(2) -0.0063(16) 0.0012(16) 0.0022(15)
C16 0.046(2) 0.0336(18) 0.042(2) 0.0003(17) 0.0077(18) -0.0005(16)
C17 0.050(2) 0.0333(18) 0.047(2) 0.0053(17) -0.0002(19) 0.0046(16)
C18 0.065(3) 0.051(2) 0.073(4) 0.010(3) -0.004(3) -0.003(2)
C19 0.069(3) 0.057(3) 0.115(6) -0.003(3) 0.007(4) -0.016(2)
C20 0.110(5) 0.093(5) 0.120(7) 0.015(5) 0.056(5) -0.028(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O3 119.2(2)
O2 S1 C6 107.96(19)
O3 S1 C6 107.89(18)
O2 S1 C1 109.71(18)
O3 S1 C1 107.5(2)
C6 S1 C1 103.51(17)
C2 O1 C3 112.9(3)
C5 C1 C2 112.2(3)
C5 C1 S1 112.9(3)
C2 C1 S1 111.3(3)
C5 C1 H1A 106.7
C2 C1 H1A 106.7
S1 C1 H1A 106.7
O1 C2 C16 112.8(3)
O1 C2 C1 108.0(3)
C16 C2 C1 114.7(3)
O1 C2 H2A 107.0
C16 C2 H2A 107.0
C1 C2 H2A 107.0
O1 C3 C4 111.0(3)
O1 C3 H3A 109.4
C4 C3 H3A 109.4
O1 C3 H3B 109.4
C4 C3 H3B 109.4
H3A C3 H3B 108.0
C3 C4 C5 110.4(3)
C3 C4 H4A 109.6
C5 C4 H4A 109.6
C3 C4 H4B 109.6
C5 C4 H4B 109.6
H4A C4 H4B 108.1
C1 C5 C4 107.8(3)
C1 C5 H5A 110.2
C4 C5 H5A 110.2
C1 C5 H5B 110.2
C4 C5 H5B 110.2
H5A C5 H5B 108.5
C7 C6 C15 121.2(4)
C7 C6 S1 120.3(3)
C15 C6 S1 118.4(3)
C6 C7 C8 119.9(4)
C6 C7 H7A 120.1
C8 C7 H7A 120.1
C13 C8 C7 119.0(3)
C13 C8 C9 118.7(3)
C7 C8 C9 122.3(4)
C10 C9 C8 120.7(4)
C10 C9 H9A 119.6
C8 C9 H9A 119.6
C9 C10 C11 120.2(4)
C9 C10 H10A 119.9
C11 C10 H10A 119.9
C12 C11 C10 121.1(4)
C12 C11 H11A 119.4
C10 C11 H11A 119.4
C11 C12 C13 120.0(4)
C11 C12 H12A 120.0
C13 C12 H12A 120.0
C14 C13 C8 119.3(3)
C14 C13 C12 121.4(3)
C8 C13 C12 119.3(3)
C15 C14 C13 121.0(4)
C15 C14 H14A 119.5
C13 C14 H14A 119.5
C14 C15 C6 119.6(4)
C14 C15 H15A 120.2
C6 C15 H15A 120.2
C2 C16 C17 113.8(3)
C2 C16 H16A 108.8
C17 C16 H16A 108.8
C2 C16 H16B 108.8
C17 C16 H16B 108.8
H16A C16 H16B 107.7
C18 C17 C16 115.4(4)
C18 C17 H17A 108.4
C16 C17 H17A 108.4
C18 C17 H17B 108.4
C16 C17 H17B 108.4
H17A C17 H17B 107.5
C17 C18 C19 112.8(4)
C17 C18 H18A 109.0
C19 C18 H18A 109.0
C17 C18 H18B 109.0
C19 C18 H18B 109.0
H18A C18 H18B 107.8
C20 C19 C18 113.0(6)
C20 C19 H19A 109.0
C18 C19 H19A 109.0
C20 C19 H19B 109.0
C18 C19 H19B 109.0
H19A C19 H19B 107.8
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.433(4)
S1 O3 1.441(3)
S1 C6 1.768(4)
S1 C1 1.779(4)
O1 C2 1.433(4)
O1 C3 1.434(5)
C1 C5 1.517(5)
C1 C2 1.548(5)
C1 H1A 1.0000
C2 C16 1.520(6)
C2 H2A 1.0000
C3 C4 1.503(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.527(5)
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.369(5)
C6 C15 1.408(6)
C7 C8 1.416(5)
C7 H7A 0.9500
C8 C13 1.412(5)
C8 C9 1.421(5)
C9 C10 1.366(5)
C9 H9A 0.9500
C10 C11 1.398(6)
C10 H10A 0.9500
C11 C12 1.364(5)
C11 H11A 0.9500
C12 C13 1.423(5)
C12 H12A 0.9500
C13 C14 1.411(5)
C14 C15 1.358(5)
C14 H14A 0.9500
C15 H15A 0.9500
C16 C17 1.530(5)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.511(6)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.551(7)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.465(10)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 S1 C1 C5 43.2(3)
O3 S1 C1 C5 174.2(3)
C6 S1 C1 C5 -71.8(3)
O2 S1 C1 C2 -83.9(3)
O3 S1 C1 C2 47.0(3)
C6 S1 C1 C2 161.1(3)
C3 O1 C2 C16 68.4(4)
C3 O1 C2 C1 -59.5(4)
C5 C1 C2 O1 57.0(4)
S1 C1 C2 O1 -175.5(3)
C5 C1 C2 C16 -69.7(4)
S1 C1 C2 C16 57.8(4)
C2 O1 C3 C4 62.0(5)
O1 C3 C4 C5 -58.3(5)
C2 C1 C5 C4 -55.0(4)
S1 C1 C5 C4 178.3(3)
C3 C4 C5 C1 54.7(5)
O2 S1 C6 C7 -3.7(4)
O3 S1 C6 C7 -133.7(3)
C1 S1 C6 C7 112.6(3)
O2 S1 C6 C15 173.6(3)
O3 S1 C6 C15 43.6(3)
C1 S1 C6 C15 -70.2(3)
C15 C6 C7 C8 -0.3(5)
S1 C6 C7 C8 176.9(3)
C6 C7 C8 C13 0.3(5)
C6 C7 C8 C9 -179.3(3)
C13 C8 C9 C10 -0.1(6)
C7 C8 C9 C10 179.5(4)
C8 C9 C10 C11 -0.8(6)
C9 C10 C11 C12 1.2(6)
C10 C11 C12 C13 -0.7(6)
C7 C8 C13 C14 -0.4(5)
C9 C8 C13 C14 179.3(3)
C7 C8 C13 C12 -179.0(3)
C9 C8 C13 C12 0.6(5)
C11 C12 C13 C14 -178.8(3)
C11 C12 C13 C8 -0.3(5)
C8 C13 C14 C15 0.5(5)
C12 C13 C14 C15 179.0(3)
C13 C14 C15 C6 -0.4(5)
C7 C6 C15 C14 0.3(5)
S1 C6 C15 C14 -176.9(3)
O1 C2 C16 C17 48.1(5)
C1 C2 C16 C17 172.3(3)
C2 C16 C17 C18 50.0(5)
C16 C17 C18 C19 174.2(5)
C17 C18 C19 C20 -77.4(7)
|
1502047.cif | #------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/20/1502047.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502047
loop_
_publ_author_name
'Zhao, Haiyan'
'Gabba\"i, Fran\,cois P'
_publ_section_title
;
Nucleophilic fluorination reactions starting from aqueous fluoride ion
solutions.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1444
_journal_page_last 1446
_journal_paper_doi 10.1021/ol200129q
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C30 H34 B F S'
_chemical_formula_weight 456.44
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 102.677(12)
_cell_angle_gamma 90.00
_cell_formula_units_Z 8
_cell_length_a 9.486(9)
_cell_length_b 26.43(2)
_cell_length_c 20.531(19)
_cell_measurement_temperature 110(2)
_cell_volume 5022(8)
_computing_cell_refinement 'Bruker APEX'
_computing_data_collection 'Bruker APEX'
_computing_data_reduction 'Bruker APEX'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.1191
_diffrn_reflns_av_sigmaI/netI 0.1365
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 31
_diffrn_reflns_limit_k_min -31
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 35548
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_min 1.28
_exptl_absorpt_coefficient_mu 0.152
_exptl_absorpt_correction_T_max 0.9954
_exptl_absorpt_correction_T_min 0.9775
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details sadabs
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.207
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1952
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.06
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.412
_refine_diff_density_min -0.422
_refine_diff_density_rms 0.074
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.058
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 595
_refine_ls_number_reflns 8830
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.058
_refine_ls_R_factor_all 0.1286
_refine_ls_R_factor_gt 0.0731
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0833P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1878
_refine_ls_wR_factor_ref 0.2132
_reflns_number_gt 5258
_reflns_number_total 8830
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200129q_si_002.cif
_cod_data_source_block sad
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'constra' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.
Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius
;
_cod_original_sg_symbol_H-M p2(1)/c
_cod_database_code 1502047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.46722(11) 0.84949(4) 0.48108(5) 0.0311(3) Uani 1 1 d .
S2 S 0.98342(11) 0.59646(4) 0.56897(5) 0.0318(3) Uani 1 1 d .
F1 F 0.7036(2) 0.89550(7) 0.48792(10) 0.0280(5) Uani 1 1 d .
F2 F 1.2198(2) 0.54958(8) 0.60601(10) 0.0308(5) Uani 1 1 d .
C3 C 0.9650(4) 0.88539(14) 0.54753(18) 0.0264(9) Uani 1 1 d .
C4 C 0.7333(4) 0.86278(13) 0.60327(18) 0.0252(9) Uani 1 1 d .
C5 C 0.6802(4) 0.79035(13) 0.44018(18) 0.0256(9) Uani 1 1 d .
C6 C 1.7171(4) 0.57231(14) 0.72987(19) 0.0305(9) Uani 1 1 d .
H6A H 1.7845 0.5902 0.7629 0.037 Uiso 1 1 calc R
C7 C 1.0376(4) 0.60024(13) 0.49077(18) 0.0267(9) Uani 1 1 d .
C8 C 1.1300(4) 0.94405(14) 0.5095(2) 0.0338(10) Uani 1 1 d .
H8A H 1.1507 0.9648 0.4750 0.041 Uiso 1 1 calc R
C9 C 0.7231(4) 0.91087(14) 0.63343(18) 0.0263(9) Uani 1 1 d .
C10 C 1.1841(4) 0.61584(14) 0.48858(18) 0.0276(9) Uani 1 1 d .
C11 C 1.5220(4) 0.52285(14) 0.63055(18) 0.0270(9) Uani 1 1 d .
C12 C 0.6740(4) 0.82129(14) 0.63290(18) 0.0283(9) Uani 1 1 d .
C13 C 1.2006(4) 0.62941(15) 0.42285(19) 0.0305(10) Uani 1 1 d .
C14 C 1.0685(4) 0.88230(14) 0.60832(19) 0.0292(9) Uani 1 1 d .
C15 C 1.3071(4) 0.61886(14) 0.54423(18) 0.0269(9) Uani 1 1 d .
C16 C 1.0484(5) 0.84964(15) 0.6656(2) 0.0362(10) Uani 1 1 d .
H16A H 0.9554 0.8321 0.6534 0.054 Uiso 1 1 calc R
H16B H 1.0502 0.8709 0.7050 0.054 Uiso 1 1 calc R
H16C H 1.1267 0.8247 0.6759 0.054 Uiso 1 1 calc R
C17 C 1.4823(4) 0.57129(14) 0.64923(19) 0.0308(10) Uani 1 1 d .
C18 C 1.2098(4) 0.68080(14) 0.66465(18) 0.0292(9) Uani 1 1 d .
C19 C 1.5881(4) 0.59600(14) 0.69918(19) 0.0279(9) Uani 1 1 d .
C20 C 0.9259(4) 0.78135(14) 0.50138(19) 0.0310(10) Uani 1 1 d .
H20A H 1.0034 0.7916 0.5365 0.037 Uiso 1 1 calc R
C21 C 0.6044(4) 0.82874(15) 0.68481(19) 0.0322(10) Uani 1 1 d .
H21A H 0.5610 0.8005 0.7012 0.039 Uiso 1 1 calc R
B1 B 0.7996(5) 0.86087(16) 0.5358(2) 0.0247(10) Uani 1 1 d .
C23 C 0.9507(5) 0.74053(15) 0.4611(2) 0.0366(11) Uani 1 1 d .
H23A H 1.0402 0.7229 0.4709 0.044 Uiso 1 1 calc R
C24 C 1.0879(5) 0.62057(15) 0.36553(19) 0.0343(10) Uani 1 1 d .
H24A H 1.1038 0.6284 0.3225 0.041 Uiso 1 1 calc R
C25 C 1.4312(4) 0.63983(15) 0.5306(2) 0.0337(10) Uani 1 1 d .
H25A H 1.5141 0.6420 0.5661 0.040 Uiso 1 1 calc R
C26 C 0.5322(4) 0.80806(14) 0.42538(18) 0.0303(10) Uani 1 1 d .
C27 C 0.7790(4) 0.95898(14) 0.6082(2) 0.0318(10) Uani 1 1 d .
H27A H 0.7613 0.9876 0.6357 0.048 Uiso 1 1 calc R
H27B H 0.7288 0.9648 0.5617 0.048 Uiso 1 1 calc R
H27C H 0.8829 0.9558 0.6107 0.048 Uiso 1 1 calc R
C28 C 1.2140(4) 0.60417(14) 0.72753(19) 0.0281(9) Uani 1 1 d .
C29 C 0.6573(4) 0.91571(14) 0.68754(19) 0.0315(10) Uani 1 1 d .
H29A H 0.6551 0.9482 0.7071 0.038 Uiso 1 1 calc R
C30 C 0.9318(5) 0.59279(14) 0.4339(2) 0.0324(10) Uani 1 1 d .
H30A H 0.8388 0.5817 0.4380 0.039 Uiso 1 1 calc R
C31 C 1.0038(4) 0.91518(14) 0.49626(19) 0.0290(9) Uani 1 1 d .
C32 C 1.2505(4) 0.62872(14) 0.67263(18) 0.0265(9) Uani 1 1 d .
B2 B 1.3186(5) 0.59464(16) 0.6192(2) 0.0275(10) Uani 1 1 d .
C34 C 0.9574(5) 0.60112(15) 0.3710(2) 0.0377(11) Uani 1 1 d .
H34A H 0.8855 0.5934 0.3322 0.045 Uiso 1 1 calc R
C35 C 0.7974(4) 0.80759(14) 0.49359(18) 0.0266(9) Uani 1 1 d .
C36 C 0.4325(5) 0.79279(16) 0.3692(2) 0.0378(11) Uani 1 1 d .
H36A H 0.3379 0.8067 0.3603 0.045 Uiso 1 1 calc R
C37 C 0.5952(5) 0.87562(15) 0.71400(19) 0.0330(10) Uani 1 1 d .
C38 C 0.4025(5) 0.90285(15) 0.4287(2) 0.0399(11) Uani 1 1 d .
H38A H 0.4848 0.9224 0.4207 0.060 Uiso 1 1 calc R
H38B H 0.3429 0.9243 0.4508 0.060 Uiso 1 1 calc R
H38C H 0.3444 0.8909 0.3860 0.060 Uiso 1 1 calc R
C39 C 1.5678(5) 0.64929(15) 0.7240(2) 0.0415(11) Uani 1 1 d .
H39A H 1.4748 0.6628 0.6998 0.062 Uiso 1 1 calc R
H39B H 1.6461 0.6711 0.7163 0.062 Uiso 1 1 calc R
H39C H 1.5694 0.6482 0.7719 0.062 Uiso 1 1 calc R
C40 C 1.4266(5) 0.49205(16) 0.5751(2) 0.0394(11) Uani 1 1 d .
H40A H 1.4743 0.4599 0.5698 0.059 Uiso 1 1 calc R
H40B H 1.4106 0.5111 0.5332 0.059 Uiso 1 1 calc R
H40C H 1.3335 0.4853 0.5868 0.059 Uiso 1 1 calc R
C41 C 0.8444(5) 0.72674(15) 0.4078(2) 0.0365(11) Uani 1 1 d .
H41A H 0.8617 0.7007 0.3786 0.044 Uiso 1 1 calc R
C42 C 0.6013(5) 0.73691(15) 0.3389(2) 0.0410(11) Uani 1 1 d .
H42A H 0.6250 0.7121 0.3096 0.049 Uiso 1 1 calc R
C43 C 1.1306(4) 0.62726(15) 0.76682(19) 0.0317(10) Uani 1 1 d .
H43A H 1.1049 0.6085 0.8020 0.038 Uiso 1 1 calc R
C44 C 1.3316(5) 0.65152(15) 0.4145(2) 0.0353(10) Uani 1 1 d .
H44A H 1.3414 0.6618 0.3713 0.042 Uiso 1 1 calc R
C45 C 0.6863(5) 0.76706(14) 0.6099(2) 0.0374(11) Uani 1 1 d .
H45A H 0.6397 0.7442 0.6364 0.056 Uiso 1 1 calc R
H45B H 0.7885 0.7580 0.6158 0.056 Uiso 1 1 calc R
H45C H 0.6385 0.7641 0.5626 0.056 Uiso 1 1 calc R
C46 C 1.1975(4) 0.91043(15) 0.6185(2) 0.0362(10) Uani 1 1 d .
H46A H 1.2669 0.9064 0.6592 0.043 Uiso 1 1 calc R
C47 C 1.1279(4) 0.70285(15) 0.7062(2) 0.0345(10) Uani 1 1 d .
H47A H 1.1017 0.7374 0.6994 0.041 Uiso 1 1 calc R
C48 C 1.7501(4) 0.52339(15) 0.71362(19) 0.0309(10) Uani 1 1 d .
C49 C 1.0836(5) 0.67723(16) 0.7561(2) 0.0351(10) Uani 1 1 d .
C50 C 1.6512(4) 0.49982(14) 0.66256(19) 0.0308(9) Uani 1 1 d .
H50A H 1.6724 0.4668 0.6489 0.037 Uiso 1 1 calc R
C51 C 0.9160(5) 0.91694(15) 0.42488(19) 0.0343(10) Uani 1 1 d .
H51A H 0.9622 0.9401 0.3986 0.051 Uiso 1 1 calc R
H51B H 0.8181 0.9289 0.4246 0.051 Uiso 1 1 calc R
H51C H 0.9110 0.8830 0.4053 0.051 Uiso 1 1 calc R
C52 C 1.2269(5) 0.94379(15) 0.5711(2) 0.0387(11) Uani 1 1 d .
C53 C 0.7079(5) 0.75124(14) 0.39608(18) 0.0322(10) Uani 1 1 d .
C54 C 1.8880(5) 0.49724(16) 0.7497(2) 0.0415(11) Uani 1 1 d .
H54A H 1.9426 0.5199 0.7839 0.062 Uiso 1 1 calc R
H54B H 1.9469 0.4887 0.7176 0.062 Uiso 1 1 calc R
H54C H 1.8634 0.4662 0.7709 0.062 Uiso 1 1 calc R
C55 C 1.4425(5) 0.65811(16) 0.4676(2) 0.0371(11) Uani 1 1 d .
H55A H 1.5278 0.6750 0.4625 0.045 Uiso 1 1 calc R
C56 C 1.2648(5) 0.55062(14) 0.7474(2) 0.0355(10) Uani 1 1 d .
H56A H 1.2292 0.5403 0.7868 0.053 Uiso 1 1 calc R
H56B H 1.3707 0.5496 0.7580 0.053 Uiso 1 1 calc R
H56C H 1.2273 0.5274 0.7104 0.053 Uiso 1 1 calc R
C57 C 1.2520(5) 0.71541(14) 0.6134(2) 0.0357(10) Uani 1 1 d .
H57A H 1.2127 0.7493 0.6173 0.053 Uiso 1 1 calc R
H57B H 1.2131 0.7021 0.5685 0.053 Uiso 1 1 calc R
H57C H 1.3576 0.7173 0.6213 0.053 Uiso 1 1 calc R
C58 C 0.5183(5) 0.88432(16) 0.7702(2) 0.0434(12) Uani 1 1 d .
H58A H 0.5263 0.9201 0.7832 0.065 Uiso 1 1 calc R
H58B H 0.5626 0.8633 0.8086 0.065 Uiso 1 1 calc R
H58C H 0.4161 0.8753 0.7553 0.065 Uiso 1 1 calc R
C59 C 0.2997(5) 0.82099(16) 0.4879(2) 0.0430(11) Uani 1 1 d .
H59A H 0.3192 0.7907 0.5160 0.064 Uiso 1 1 calc R
H59B H 0.2447 0.8115 0.4434 0.064 Uiso 1 1 calc R
H59C H 0.2435 0.8451 0.5081 0.064 Uiso 1 1 calc R
C60 C 0.4686(5) 0.75714(16) 0.3251(2) 0.0408(11) Uani 1 1 d .
H60A H 0.4001 0.7475 0.2860 0.049 Uiso 1 1 calc R
C61 C 0.9088(5) 0.53394(16) 0.5690(2) 0.0449(12) Uani 1 1 d .
H61A H 0.9872 0.5090 0.5768 0.067 Uiso 1 1 calc R
H61B H 0.8436 0.5273 0.5257 0.067 Uiso 1 1 calc R
H61C H 0.8549 0.5314 0.6045 0.067 Uiso 1 1 calc R
C62 C 0.8209(5) 0.63348(19) 0.5544(2) 0.0491(12) Uani 1 1 d .
H62A H 0.8453 0.6694 0.5530 0.074 Uiso 1 1 calc R
H62B H 0.7703 0.6276 0.5906 0.074 Uiso 1 1 calc R
H62C H 0.7582 0.6236 0.5118 0.074 Uiso 1 1 calc R
C63 C 0.9940(5) 0.70263(17) 0.7990(2) 0.0474(12) Uani 1 1 d .
H63A H 0.9718 0.7374 0.7834 0.071 Uiso 1 1 calc R
H63B H 1.0481 0.7032 0.8455 0.071 Uiso 1 1 calc R
H63C H 0.9037 0.6838 0.7960 0.071 Uiso 1 1 calc R
C64 C 1.3628(5) 0.97584(17) 0.5850(3) 0.0552(14) Uani 1 1 d .
H64A H 1.4166 0.9699 0.6308 0.083 Uiso 1 1 calc R
H64B H 1.3364 1.0117 0.5794 0.083 Uiso 1 1 calc R
H64C H 1.4231 0.9667 0.5537 0.083 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0326(6) 0.0234(5) 0.0351(6) 0.0025(4) 0.0025(5) -0.0003(4)
S2 0.0286(6) 0.0313(6) 0.0330(6) 0.0012(4) 0.0013(4) -0.0012(5)
F1 0.0344(13) 0.0177(11) 0.0294(12) 0.0043(9) 0.0011(10) 0.0028(10)
F2 0.0313(13) 0.0220(12) 0.0356(12) 0.0023(9) -0.0001(10) -0.0038(10)
C3 0.031(2) 0.0153(19) 0.031(2) 0.0010(16) 0.0027(18) 0.0033(17)
C4 0.027(2) 0.0159(19) 0.029(2) -0.0026(16) -0.0025(17) 0.0015(16)
C5 0.035(2) 0.0168(19) 0.0238(19) 0.0023(15) 0.0028(17) -0.0017(17)
C6 0.029(2) 0.025(2) 0.033(2) 0.0004(17) -0.0033(18) -0.0013(18)
C7 0.033(2) 0.0158(19) 0.027(2) -0.0027(16) -0.0027(17) -0.0001(17)
C8 0.035(3) 0.018(2) 0.048(3) 0.0092(18) 0.008(2) -0.0007(18)
C9 0.030(2) 0.021(2) 0.024(2) -0.0011(16) -0.0024(17) 0.0012(17)
C10 0.033(2) 0.017(2) 0.031(2) 0.0010(16) 0.0023(18) 0.0021(17)
C11 0.030(2) 0.024(2) 0.027(2) -0.0025(16) 0.0065(18) -0.0045(18)
C12 0.035(2) 0.019(2) 0.028(2) -0.0004(16) 0.0000(18) -0.0012(17)
C13 0.036(3) 0.025(2) 0.029(2) -0.0007(17) 0.0037(18) 0.0057(18)
C14 0.033(2) 0.018(2) 0.032(2) -0.0015(16) -0.0022(18) 0.0020(17)
C15 0.026(2) 0.020(2) 0.032(2) -0.0004(16) 0.0015(18) 0.0041(17)
C16 0.040(3) 0.028(2) 0.034(2) 0.0010(18) -0.0064(19) 0.0048(19)
C17 0.040(3) 0.022(2) 0.028(2) 0.0036(17) 0.0038(18) -0.0012(19)
C18 0.029(2) 0.026(2) 0.027(2) 0.0010(17) -0.0050(18) -0.0001(18)
C19 0.030(2) 0.019(2) 0.034(2) -0.0011(17) 0.0037(18) -0.0010(17)
C20 0.038(3) 0.023(2) 0.030(2) 0.0024(17) 0.0019(18) 0.0012(19)
C21 0.043(3) 0.024(2) 0.029(2) 0.0065(17) 0.0062(19) -0.0023(19)
B1 0.029(3) 0.019(2) 0.022(2) 0.0028(17) -0.0047(19) 0.0043(19)
C23 0.047(3) 0.025(2) 0.038(2) 0.0060(19) 0.010(2) 0.009(2)
C24 0.047(3) 0.026(2) 0.027(2) -0.0010(17) 0.003(2) 0.007(2)
C25 0.031(3) 0.030(2) 0.038(2) 0.0049(18) 0.0035(19) -0.0024(19)
C26 0.039(3) 0.019(2) 0.028(2) 0.0018(16) -0.0028(19) -0.0058(18)
C27 0.038(3) 0.019(2) 0.037(2) -0.0048(17) 0.0058(19) -0.0020(18)
C28 0.030(2) 0.020(2) 0.029(2) 0.0003(16) -0.0045(17) -0.0015(18)
C29 0.041(3) 0.020(2) 0.029(2) -0.0020(17) -0.0003(19) 0.0040(18)
C30 0.032(2) 0.022(2) 0.039(2) -0.0011(18) -0.0002(19) -0.0025(18)
C31 0.034(2) 0.020(2) 0.031(2) 0.0021(17) 0.0011(18) 0.0053(18)
C32 0.023(2) 0.018(2) 0.033(2) 0.0030(16) -0.0061(17) -0.0006(16)
B2 0.030(3) 0.018(2) 0.032(2) 0.0006(18) 0.000(2) -0.005(2)
C34 0.048(3) 0.029(2) 0.029(2) -0.0066(18) -0.007(2) 0.004(2)
C35 0.033(2) 0.018(2) 0.027(2) 0.0018(16) 0.0013(17) 0.0006(18)
C36 0.039(3) 0.032(2) 0.038(2) 0.0061(19) -0.002(2) -0.008(2)
C37 0.042(3) 0.026(2) 0.029(2) 0.0021(18) 0.0029(19) 0.0068(19)
C38 0.044(3) 0.028(2) 0.043(3) 0.0082(19) -0.001(2) 0.005(2)
C39 0.037(3) 0.025(2) 0.054(3) -0.003(2) -0.006(2) -0.001(2)
C40 0.037(3) 0.037(3) 0.039(2) -0.012(2) -0.003(2) 0.001(2)
C41 0.057(3) 0.017(2) 0.038(2) -0.0022(17) 0.015(2) 0.004(2)
C42 0.068(3) 0.020(2) 0.033(2) -0.0010(18) 0.007(2) -0.009(2)
C43 0.031(2) 0.033(2) 0.029(2) 0.0025(18) 0.0002(18) -0.0030(19)
C44 0.040(3) 0.034(2) 0.033(2) 0.0110(19) 0.009(2) 0.009(2)
C45 0.056(3) 0.017(2) 0.040(2) -0.0002(18) 0.014(2) -0.006(2)
C46 0.033(3) 0.025(2) 0.044(3) 0.0002(19) -0.006(2) 0.0020(19)
C47 0.035(3) 0.024(2) 0.039(2) 0.0011(19) -0.002(2) 0.0023(19)
C48 0.031(2) 0.028(2) 0.032(2) 0.0040(17) 0.0049(18) 0.0022(19)
C49 0.035(3) 0.034(2) 0.035(2) -0.0083(19) 0.0037(19) -0.002(2)
C50 0.035(3) 0.020(2) 0.037(2) -0.0012(17) 0.0073(19) -0.0019(18)
C51 0.041(3) 0.031(2) 0.032(2) 0.0034(18) 0.0107(19) 0.004(2)
C52 0.031(3) 0.026(2) 0.055(3) 0.001(2) 0.002(2) 0.0019(19)
C53 0.052(3) 0.019(2) 0.024(2) 0.0002(16) 0.0049(19) -0.0046(19)
C54 0.038(3) 0.033(2) 0.048(3) 0.002(2) -0.003(2) 0.007(2)
C55 0.031(3) 0.034(2) 0.045(3) 0.008(2) 0.007(2) 0.003(2)
C56 0.050(3) 0.024(2) 0.031(2) 0.0067(18) 0.006(2) 0.000(2)
C57 0.043(3) 0.022(2) 0.038(2) 0.0073(18) 0.000(2) 0.0044(19)
C58 0.063(3) 0.032(2) 0.035(2) 0.0081(19) 0.011(2) 0.010(2)
C59 0.037(3) 0.030(2) 0.062(3) 0.005(2) 0.010(2) -0.003(2)
C60 0.054(3) 0.032(2) 0.030(2) -0.0018(19) -0.005(2) -0.012(2)
C61 0.045(3) 0.035(3) 0.050(3) 0.006(2) 0.002(2) -0.019(2)
C62 0.034(3) 0.059(3) 0.055(3) 0.006(2) 0.011(2) 0.013(2)
C63 0.052(3) 0.041(3) 0.050(3) -0.006(2) 0.014(2) 0.005(2)
C64 0.036(3) 0.032(3) 0.090(4) 0.007(3) -0.002(3) -0.006(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C26 S1 C59 103.2(2)
C26 S1 C38 102.6(2)
C59 S1 C38 100.6(2)
C7 S2 C62 103.0(2)
C7 S2 C61 104.0(2)
C62 S2 C61 100.2(2)
C14 C3 C31 116.3(4)
C14 C3 B1 123.8(3)
C31 C3 B1 119.7(3)
C9 C4 C12 115.4(3)
C9 C4 B1 117.9(3)
C12 C4 B1 126.5(3)
C53 C5 C26 113.8(3)
C53 C5 C35 119.1(4)
C26 C5 C35 127.1(3)
C48 C6 C19 122.1(4)
C48 C6 H6A 119.0
C19 C6 H6A 119.0
C30 C7 C10 122.4(4)
C30 C7 S2 116.9(3)
C10 C7 S2 120.4(3)
C52 C8 C31 122.8(4)
C52 C8 H8A 118.6
C31 C8 H8A 118.6
C29 C9 C4 120.8(4)
C29 C9 C27 116.6(3)
C4 C9 C27 122.6(3)
C13 C10 C15 119.5(4)
C13 C10 C7 113.6(3)
C15 C10 C7 126.9(3)
C50 C11 C17 121.8(4)
C50 C11 C40 115.7(3)
C17 C11 C40 122.5(4)
C21 C12 C4 121.1(3)
C21 C12 C45 117.0(3)
C4 C12 C45 121.8(3)
C44 C13 C24 119.1(4)
C44 C13 C10 119.7(4)
C24 C13 C10 121.2(4)
C46 C14 C3 120.9(4)
C46 C14 C16 116.2(3)
C3 C14 C16 122.8(4)
C25 C15 C10 115.9(4)
C25 C15 B2 117.4(3)
C10 C15 B2 126.4(3)
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C11 C17 C19 115.0(4)
C11 C17 B2 121.4(3)
C19 C17 B2 123.4(3)
C47 C18 C32 120.2(4)
C47 C18 C57 116.0(3)
C32 C18 C57 123.8(4)
C6 C19 C17 121.9(3)
C6 C19 C39 115.2(3)
C17 C19 C39 122.9(4)
C35 C20 C23 125.0(4)
C35 C20 H20A 117.5
C23 C20 H20A 117.5
C12 C21 C37 123.0(4)
C12 C21 H21A 118.5
C37 C21 H21A 118.5
F1 B1 C4 104.1(3)
F1 B1 C35 103.9(3)
C4 B1 C35 120.4(3)
F1 B1 C3 106.0(3)
C4 B1 C3 112.9(3)
C35 B1 C3 108.1(3)
C41 C23 C20 119.0(4)
C41 C23 H23A 120.5
C20 C23 H23A 120.5
C34 C24 C13 121.5(4)
C34 C24 H24A 119.3
C13 C24 H24A 119.3
C15 C25 C55 124.3(4)
C15 C25 H25A 117.8
C55 C25 H25A 117.8
C36 C26 C5 122.4(4)
C36 C26 S1 116.4(3)
C5 C26 S1 121.2(3)
C9 C27 H27A 109.5
C9 C27 H27B 109.5
H27A C27 H27B 109.5
C9 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C43 C28 C32 122.3(3)
C43 C28 C56 116.1(4)
C32 C28 C56 121.7(4)
C37 C29 C9 123.2(4)
C37 C29 H29A 118.4
C9 C29 H29A 118.4
C7 C30 C34 121.6(4)
C7 C30 H30A 119.2
C34 C30 H30A 119.2
C8 C31 C3 120.5(3)
C8 C31 C51 115.9(4)
C3 C31 C51 123.6(4)
C28 C32 C18 115.3(4)
C28 C32 B2 118.6(3)
C18 C32 B2 125.7(3)
F2 B2 C15 103.2(3)
F2 B2 C32 103.4(3)
C15 B2 C32 116.8(3)
F2 B2 C17 105.5(3)
C15 B2 C17 110.8(3)
C32 B2 C17 115.2(3)
C24 C34 C30 119.0(4)
C24 C34 H34A 120.5
C30 C34 H34A 120.5
C20 C35 C5 116.1(3)
C20 C35 B1 117.3(3)
C5 C35 B1 125.7(3)
C26 C36 C60 121.1(4)
C26 C36 H36A 119.4
C60 C36 H36A 119.4
C29 C37 C21 116.3(4)
C29 C37 C58 120.2(4)
C21 C37 C58 123.5(4)
S1 C38 H38A 109.5
S1 C38 H38B 109.5
H38A C38 H38B 109.5
S1 C38 H38C 109.5
H38A C38 H38C 109.5
H38B C38 H38C 109.5
C19 C39 H39A 109.5
C19 C39 H39B 109.5
H39A C39 H39B 109.5
C19 C39 H39C 109.5
H39A C39 H39C 109.5
H39B C39 H39C 109.5
C11 C40 H40A 109.5
C11 C40 H40B 109.5
H40A C40 H40B 109.5
C11 C40 H40C 109.5
H40A C40 H40C 109.5
H40B C40 H40C 109.5
C23 C41 C53 120.0(4)
C23 C41 H41A 120.0
C53 C41 H41A 120.0
C60 C42 C53 122.3(4)
C60 C42 H42A 118.8
C53 C42 H42A 118.8
C28 C43 C49 121.8(4)
C28 C43 H43A 119.1
C49 C43 H43A 119.1
C55 C44 C13 120.3(4)
C55 C44 H44A 119.9
C13 C44 H44A 119.9
C12 C45 H45A 109.5
C12 C45 H45B 109.5
H45A C45 H45B 109.5
C12 C45 H45C 109.5
H45A C45 H45C 109.5
H45B C45 H45C 109.5
C52 C46 C14 122.3(4)
C52 C46 H46A 118.9
C14 C46 H46A 118.9
C49 C47 C18 123.5(4)
C49 C47 H47A 118.2
C18 C47 H47A 118.2
C6 C48 C50 116.6(4)
C6 C48 C54 121.4(4)
C50 C48 C54 122.0(4)
C47 C49 C43 116.5(4)
C47 C49 C63 121.5(4)
C43 C49 C63 122.0(4)
C48 C50 C11 122.4(4)
C48 C50 H50A 118.8
C11 C50 H50A 118.8
C31 C51 H51A 109.5
C31 C51 H51B 109.5
H51A C51 H51B 109.5
C31 C51 H51C 109.5
H51A C51 H51C 109.5
H51B C51 H51C 109.5
C46 C52 C8 116.6(4)
C46 C52 C64 121.1(4)
C8 C52 C64 122.2(4)
C41 C53 C42 118.4(4)
C41 C53 C5 120.5(4)
C42 C53 C5 121.1(4)
C48 C54 H54A 109.5
C48 C54 H54B 109.5
H54A C54 H54B 109.5
C48 C54 H54C 109.5
H54A C54 H54C 109.5
H54B C54 H54C 109.5
C44 C55 C25 119.7(4)
C44 C55 H55A 120.2
C25 C55 H55A 120.2
C28 C56 H56A 109.5
C28 C56 H56B 109.5
H56A C56 H56B 109.5
C28 C56 H56C 109.5
H56A C56 H56C 109.5
H56B C56 H56C 109.5
C18 C57 H57A 109.5
C18 C57 H57B 109.5
H57A C57 H57B 109.5
C18 C57 H57C 109.5
H57A C57 H57C 109.5
H57B C57 H57C 109.5
C37 C58 H58A 109.5
C37 C58 H58B 109.5
H58A C58 H58B 109.5
C37 C58 H58C 109.5
H58A C58 H58C 109.5
H58B C58 H58C 109.5
S1 C59 H59A 109.5
S1 C59 H59B 109.5
H59A C59 H59B 109.5
S1 C59 H59C 109.5
H59A C59 H59C 109.5
H59B C59 H59C 109.5
C42 C60 C36 118.9(4)
C42 C60 H60A 120.6
C36 C60 H60A 120.6
S2 C61 H61A 109.5
S2 C61 H61B 109.5
H61A C61 H61B 109.5
S2 C61 H61C 109.5
H61A C61 H61C 109.5
H61B C61 H61C 109.5
S2 C62 H62A 109.5
S2 C62 H62B 109.5
H62A C62 H62B 109.5
S2 C62 H62C 109.5
H62A C62 H62C 109.5
H62B C62 H62C 109.5
C49 C63 H63A 109.5
C49 C63 H63B 109.5
H63A C63 H63B 109.5
C49 C63 H63C 109.5
H63A C63 H63C 109.5
H63B C63 H63C 109.5
C52 C64 H64A 109.5
C52 C64 H64B 109.5
H64A C64 H64B 109.5
C52 C64 H64C 109.5
H64A C64 H64C 109.5
H64B C64 H64C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C26 1.788(4)
S1 C59 1.792(5)
S1 C38 1.798(4)
S2 C7 1.793(4)
S2 C62 1.795(5)
S2 C61 1.798(4)
F1 B1 1.497(4)
F2 B2 1.503(5)
C3 C14 1.410(5)
C3 C31 1.426(5)
C3 B1 1.666(6)
C4 C9 1.426(5)
C4 C12 1.428(5)
C4 B1 1.643(6)
C5 C53 1.436(5)
C5 C26 1.447(6)
C5 C35 1.453(5)
C6 C48 1.388(5)
C6 C19 1.396(5)
C6 H6A 0.9500
C7 C30 1.377(5)
C7 C10 1.459(6)
C8 C52 1.390(6)
C8 C31 1.396(5)
C8 H8A 0.9500
C9 C29 1.395(6)
C9 C27 1.512(5)
C10 C13 1.438(5)
C10 C15 1.445(5)
C11 C50 1.397(5)
C11 C17 1.411(5)
C11 C40 1.525(5)
C12 C21 1.385(6)
C12 C45 1.522(5)
C13 C44 1.417(6)
C13 C24 1.425(6)
C14 C46 1.408(6)
C14 C16 1.505(5)
C15 C25 1.385(5)
C15 B2 1.649(6)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 C19 1.426(5)
C17 B2 1.659(6)
C18 C47 1.400(6)
C18 C32 1.429(5)
C18 C57 1.513(5)
C19 C39 1.525(5)
C20 C35 1.381(5)
C20 C23 1.410(5)
C20 H20A 0.9500
C21 C37 1.387(5)
C21 H21A 0.9500
B1 C35 1.652(6)
C23 C41 1.365(6)
C23 H23A 0.9500
C24 C34 1.368(6)
C24 H24A 0.9500
C25 C55 1.406(6)
C25 H25A 0.9500
C26 C36 1.382(5)
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
C28 C43 1.389(6)
C28 C32 1.408(5)
C28 C56 1.522(5)
C29 C37 1.381(6)
C29 H29A 0.9500
C30 C34 1.384(6)
C30 H30A 0.9500
C31 C51 1.519(5)
C32 B2 1.656(6)
C34 H34A 0.9500
C36 C60 1.401(6)
C36 H36A 0.9500
C37 C58 1.512(6)
C38 H38A 0.9800
C38 H38B 0.9800
C38 H38C 0.9800
C39 H39A 0.9800
C39 H39B 0.9800
C39 H39C 0.9800
C40 H40A 0.9800
C40 H40B 0.9800
C40 H40C 0.9800
C41 C53 1.420(6)
C41 H41A 0.9500
C42 C60 1.339(6)
C42 C53 1.422(6)
C42 H42A 0.9500
C43 C49 1.396(6)
C43 H43A 0.9500
C44 C55 1.350(6)
C44 H44A 0.9500
C45 H45A 0.9800
C45 H45B 0.9800
C45 H45C 0.9800
C46 C52 1.386(6)
C46 H46A 0.9500
C47 C49 1.370(6)
C47 H47A 0.9500
C48 C50 1.391(5)
C48 C54 1.520(5)
C49 C63 1.510(6)
C50 H50A 0.9500
C51 H51A 0.9800
C51 H51B 0.9800
C51 H51C 0.9800
C52 C64 1.516(6)
C54 H54A 0.9800
C54 H54B 0.9800
C54 H54C 0.9800
C55 H55A 0.9500
C56 H56A 0.9800
C56 H56B 0.9800
C56 H56C 0.9800
C57 H57A 0.9800
C57 H57B 0.9800
C57 H57C 0.9800
C58 H58A 0.9800
C58 H58B 0.9800
C58 H58C 0.9800
C59 H59A 0.9800
C59 H59B 0.9800
C59 H59C 0.9800
C60 H60A 0.9500
C61 H61A 0.9800
C61 H61B 0.9800
C61 H61C 0.9800
C62 H62A 0.9800
C62 H62B 0.9800
C62 H62C 0.9800
C63 H63A 0.9800
C63 H63B 0.9800
C63 H63C 0.9800
C64 H64A 0.9800
C64 H64B 0.9800
C64 H64C 0.9800
|
1502048.cif | #------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/20/1502048.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502048
loop_
_publ_author_name
'Katsuta, Shuhei'
'Miyagi, Daichi'
'Yamada, Hiroko'
'Okujima, Tetsuo'
'Mori, Shigeki'
'Nakayama, Ken-ichi'
'Uno, Hidemitsu'
_publ_section_title
;
Synthesis, properties, and ambipolar organic field-effect transistor
performances of symmetrically cyanated pentacene and naphthacene as
air-stable acene derivatives.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1454
_journal_page_last 1457
_journal_paper_doi 10.1021/ol200145r
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C20 H10 N2 '
_chemical_formula_sum 'C20 H10 N2'
_chemical_formula_weight 278.31
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_Int_Tables_number 2
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha 94.054(2)
_cell_angle_beta 92.358(2)
_cell_angle_gamma 91.872(2)
_cell_formula_units_Z 2
_cell_length_a 3.79021(12)
_cell_length_b 12.8608(4)
_cell_length_c 13.5027(4)
_cell_measurement_reflns_used 2712
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 68.1
_cell_measurement_theta_min 3.3
_cell_volume 655.57(4)
_computing_cell_refinement PROCESS-AUTO
_computing_data_collection PROCESS-AUTO
_computing_data_reduction CrystalStructure
_computing_publication_material 'CrystalStructure 3.8.2'
_computing_structure_refinement SHELXL97
_computing_structure_solution SIR2004
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method \w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'VariMax 2.4 kW Ultra fine focus'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54187
_diffrn_reflns_av_R_equivalents 0.0511
_diffrn_reflns_av_sigmaI/netI 0.0731
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 7102
_diffrn_reflns_theta_full 68.14
_diffrn_reflns_theta_max 68.14
_diffrn_reflns_theta_min 3.45
_exptl_absorpt_coefficient_mu 0.656
_exptl_absorpt_correction_T_max 0.987
_exptl_absorpt_correction_T_min 0.705
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.410
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 288
_exptl_crystal_size_max 0.13
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.633
_refine_diff_density_min -0.244
_refine_diff_density_rms 0.068
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.079
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 200
_refine_ls_number_reflns 2340
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.079
_refine_ls_R_factor_all 0.1141
_refine_ls_R_factor_gt 0.0677
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1502
_refine_ls_wR_factor_ref 0.1776
_reflns_number_gt 1115
_reflns_number_total 2340
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200145r_si_002.cif
_cod_data_source_block '_20100607_3'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.
Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius
;
_cod_original_cell_volume 655.57(3)
_cod_original_formula_sum 'C20 H10 N2 '
_cod_database_code 1502048
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.5995(6) 0.53164(18) 0.17731(17) 0.0394(6) Uani 1 1 d .
N2 N -0.2224(6) -0.03913(18) 0.23172(16) 0.0392(6) Uani 1 1 d .
C1 C -0.1714(7) 0.1348(2) 0.03911(19) 0.0310(7) Uani 1 1 d .
H1 H -0.2649 0.0661 0.0443 0.037 Uiso 1 1 calc R
C2 C -0.2110(7) 0.1802(2) -0.0481(2) 0.0341(7) Uani 1 1 d .
H2 H -0.3321 0.1429 -0.1033 0.041 Uiso 1 1 calc R
C3 C -0.0736(7) 0.2827(2) -0.0578(2) 0.0350(7) Uani 1 1 d .
H3 H -0.1032 0.3132 -0.1196 0.042 Uiso 1 1 calc R
C4 C 0.0991(7) 0.3376(2) 0.01977(19) 0.0317(7) Uani 1 1 d .
H4 H 0.1905 0.4061 0.0119 0.038 Uiso 1 1 calc R
C5 C 0.1454(7) 0.2934(2) 0.11375(19) 0.0302(7) Uani 1 1 d .
C6 C 0.3216(7) 0.34776(19) 0.19605(19) 0.0284(6) Uani 1 1 d .
C7 C 0.3649(6) 0.3037(2) 0.28975(19) 0.0274(6) Uani 1 1 d .
C8 C 0.5393(7) 0.3594(2) 0.37308(19) 0.0301(6) Uani 1 1 d .
H8 H 0.6274 0.4287 0.3674 0.036 Uiso 1 1 calc R
C9 C 0.5830(7) 0.31373(19) 0.4632(2) 0.0289(6) Uani 1 1 d .
C10 C 0.7585(7) 0.3684(2) 0.54817(19) 0.0339(7) Uani 1 1 d .
H10 H 0.8429 0.4382 0.5440 0.041 Uiso 1 1 calc R
C11 C 0.8065(7) 0.3220(2) 0.6349(2) 0.0367(7) Uani 1 1 d .
H11 H 0.9267 0.3593 0.6902 0.044 Uiso 1 1 calc R
C12 C 0.6784(7) 0.2182(2) 0.6434(2) 0.0364(7) Uani 1 1 d .
H12 H 0.7149 0.1865 0.7043 0.044 Uiso 1 1 calc R
C13 C 0.5039(7) 0.1637(2) 0.56521(19) 0.0344(7) Uani 1 1 d .
H13 H 0.4153 0.0949 0.5727 0.041 Uiso 1 1 calc R
C14 C 0.4516(7) 0.20863(19) 0.47160(19) 0.0289(7) Uani 1 1 d .
C15 C 0.2757(7) 0.1541(2) 0.39077(19) 0.0302(7) Uani 1 1 d .
H15 H 0.1849 0.0853 0.3973 0.036 Uiso 1 1 calc R
C16 C 0.2297(7) 0.19941(19) 0.29896(18) 0.0270(6) Uani 1 1 d .
C17 C 0.0513(7) 0.14559(19) 0.21549(19) 0.0282(6) Uani 1 1 d .
C18 C 0.0080(7) 0.1887(2) 0.1229(2) 0.0291(6) Uani 1 1 d .
C19 C 0.4725(7) 0.4507(2) 0.18521(19) 0.0332(7) Uani 1 1 d .
C20 C -0.0968(7) 0.0421(2) 0.22519(19) 0.0323(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0474(16) 0.0329(14) 0.0376(14) 0.0051(11) -0.0011(12) -0.0032(12)
N2 0.0463(16) 0.0331(13) 0.0376(14) 0.0024(11) -0.0010(12) -0.0059(12)
C1 0.0283(16) 0.0289(15) 0.0352(16) -0.0005(12) 0.0014(13) -0.0019(12)
C2 0.0355(17) 0.0386(17) 0.0274(15) -0.0007(13) -0.0026(13) 0.0000(13)
C3 0.0384(17) 0.0380(17) 0.0286(15) 0.0029(13) -0.0007(13) 0.0061(13)
C4 0.0342(16) 0.0316(15) 0.0298(15) 0.0039(12) 0.0033(13) 0.0003(12)
C5 0.0285(16) 0.0329(15) 0.0295(15) 0.0016(12) 0.0036(12) 0.0041(12)
C6 0.0275(15) 0.0266(14) 0.0307(15) -0.0013(12) 0.0018(12) 0.0004(12)
C7 0.0245(15) 0.0301(15) 0.0278(15) 0.0020(12) 0.0048(12) 0.0031(12)
C8 0.0283(15) 0.0300(15) 0.0318(15) 0.0012(12) 0.0026(12) 0.0005(12)
C9 0.0278(15) 0.0294(15) 0.0291(14) -0.0008(12) 0.0015(12) -0.0009(12)
C10 0.0338(17) 0.0334(15) 0.0339(16) -0.0014(13) 0.0017(13) -0.0013(12)
C11 0.0379(18) 0.0411(17) 0.0304(16) -0.0016(13) 0.0003(13) 0.0001(13)
C12 0.0398(18) 0.0404(17) 0.0293(15) 0.0047(13) -0.0003(13) 0.0011(13)
C13 0.0370(17) 0.0364(16) 0.0303(15) 0.0055(12) 0.0009(13) 0.0000(13)
C14 0.0276(15) 0.0285(14) 0.0307(15) 0.0018(12) 0.0024(12) 0.0016(12)
C15 0.0285(15) 0.0312(15) 0.0309(15) 0.0021(12) 0.0001(12) 0.0019(12)
C16 0.0281(16) 0.0255(14) 0.0272(15) -0.0007(11) 0.0022(12) -0.0006(11)
C17 0.0296(16) 0.0250(14) 0.0297(14) -0.0008(12) 0.0023(12) 0.0013(12)
C18 0.0267(15) 0.0302(15) 0.0302(15) 0.0007(12) 0.0014(12) 0.0014(12)
C19 0.0355(17) 0.0345(16) 0.0294(15) 0.0021(13) -0.0019(13) 0.0027(13)
C20 0.0349(17) 0.0349(16) 0.0265(15) -0.0010(12) -0.0018(12) 0.0013(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C18 120.9(3)
C2 C1 H1 119.6
C18 C1 H1 119.6
C1 C2 C3 120.7(2)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 120.8(3)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.6(3)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 122.4(3)
C6 C5 C18 119.3(2)
C4 C5 C18 118.4(2)
C5 C6 C7 122.2(3)
C5 C6 C19 119.1(2)
C7 C6 C19 118.7(2)
C8 C7 C6 122.0(3)
C8 C7 C16 119.4(2)
C6 C7 C16 118.6(2)
C9 C8 C7 120.7(3)
C9 C8 H8 119.6
C7 C8 H8 119.6
C8 C9 C10 121.7(2)
C8 C9 C14 119.6(2)
C10 C9 C14 118.6(2)
C11 C10 C9 121.1(3)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 120.5(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 120.6(3)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 121.0(3)
C12 C13 H13 119.5
C14 C13 H13 119.5
C15 C14 C13 121.9(3)
C15 C14 C9 119.9(2)
C13 C14 C9 118.2(2)
C14 C15 C16 121.0(3)
C14 C15 H15 119.5
C16 C15 H15 119.5
C15 C16 C17 122.1(3)
C15 C16 C7 119.3(2)
C17 C16 C7 118.6(2)
C18 C17 C16 123.0(3)
C18 C17 C20 118.1(2)
C16 C17 C20 118.9(2)
C17 C18 C1 123.0(3)
C17 C18 C5 118.3(2)
C1 C18 C5 118.6(2)
N1 C19 C6 178.4(3)
N2 C20 C17 178.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C19 1.146(3)
N2 C20 1.145(3)
C1 C2 1.356(4)
C1 C18 1.421(3)
C1 H1 0.9500
C2 C3 1.418(4)
C2 H2 0.9500
C3 C4 1.354(3)
C3 H3 0.9500
C4 C5 1.434(4)
C4 H4 0.9500
C5 C6 1.403(3)
C5 C18 1.442(4)
C6 C7 1.428(4)
C6 C19 1.444(4)
C7 C8 1.418(3)
C7 C16 1.435(3)
C8 C9 1.394(4)
C8 H8 0.9500
C9 C10 1.430(3)
C9 C14 1.439(4)
C10 C11 1.360(4)
C10 H10 0.9500
C11 C12 1.419(4)
C11 H11 0.9500
C12 C13 1.361(3)
C12 H12 0.9500
C13 C14 1.435(4)
C13 H13 0.9500
C14 C15 1.389(3)
C15 C16 1.413(4)
C15 H15 0.9500
C16 C17 1.415(3)
C17 C18 1.408(4)
C17 C20 1.444(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C18 C1 C2 C3 0.1(4)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 -179.8(2)
C3 C4 C5 C18 0.9(4)
C4 C5 C6 C7 179.5(2)
C18 C5 C6 C7 -1.1(4)
C4 C5 C6 C19 -2.1(4)
C18 C5 C6 C19 177.3(2)
C5 C6 C7 C8 -179.2(2)
C19 C6 C7 C8 2.4(4)
C5 C6 C7 C16 1.4(4)
C19 C6 C7 C16 -177.0(2)
C6 C7 C8 C9 -178.9(2)
C16 C7 C8 C9 0.5(4)
C7 C8 C9 C10 179.9(2)
C7 C8 C9 C14 0.4(4)
C8 C9 C10 C11 -178.4(2)
C14 C9 C10 C11 1.1(4)
C9 C10 C11 C12 -0.9(4)
C10 C11 C12 C13 -0.4(4)
C11 C12 C13 C14 1.4(4)
C12 C13 C14 C15 179.7(2)
C12 C13 C14 C9 -1.2(4)
C8 C9 C14 C15 -1.4(4)
C10 C9 C14 C15 179.1(2)
C8 C9 C14 C13 179.5(2)
C10 C9 C14 C13 -0.1(4)
C13 C14 C15 C16 -179.4(2)
C9 C14 C15 C16 1.4(4)
C14 C15 C16 C17 -180.0(2)
C14 C15 C16 C7 -0.5(4)
C8 C7 C16 C15 -0.5(4)
C6 C7 C16 C15 179.0(2)
C8 C7 C16 C17 179.0(2)
C6 C7 C16 C17 -1.6(4)
C15 C16 C17 C18 -178.9(2)
C7 C16 C17 C18 1.6(4)
C15 C16 C17 C20 1.7(4)
C7 C16 C17 C20 -177.7(2)
C16 C17 C18 C1 -179.9(2)
C20 C17 C18 C1 -0.5(4)
C16 C17 C18 C5 -1.4(4)
C20 C17 C18 C5 178.0(2)
C2 C1 C18 C17 179.0(2)
C2 C1 C18 C5 0.5(4)
C6 C5 C18 C17 1.1(4)
C4 C5 C18 C17 -179.6(2)
C6 C5 C18 C1 179.7(2)
C4 C5 C18 C1 -0.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26666707
|
1502049.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502049.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502049
loop_
_publ_author_name
'Hovey, M. Todd'
'Eklund, Emily J.'
'Pike, Robert D.'
'Mainkar, Anshul A.'
'Scheerer, Jonathan R.'
_publ_section_title
;
Synthesis of (+-)-acetylnorloline via stereoselective tethered
aminohydroxylation.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1246
_journal_page_last 1249
_journal_paper_doi 10.1021/ol200155p
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration unk
_chemical_formula_moiety 'C8 H10 N2 O3'
_chemical_formula_sum 'C8 H10 N2 O3'
_chemical_formula_weight 182.18
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 5.18270(10)
_cell_length_b 8.0456(2)
_cell_length_c 20.4481(5)
_cell_measurement_reflns_used 3327
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 67.73
_cell_measurement_theta_min 4.32
_cell_volume 852.64(3)
_computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection 'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction SAINTPLUS
_computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)'
_computing_publication_material 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement 'XSHELL (Bruker, 2004)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker SMART APEX II CCD'
_diffrn_measurement_method '\w and \y'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0402
_diffrn_reflns_av_sigmaI/netI 0.0224
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 9183
_diffrn_reflns_theta_full 66.89
_diffrn_reflns_theta_max 66.89
_diffrn_reflns_theta_min 4.32
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.931
_exptl_absorpt_correction_T_max 0.9726
_exptl_absorpt_correction_T_min 0.7129
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.419
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description blade
_exptl_crystal_F_000 384
_exptl_crystal_size_max 0.39
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.168
_refine_diff_density_min -0.138
_refine_diff_density_rms 0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.0(3)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.096
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 118
_refine_ls_number_reflns 1505
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.096
_refine_ls_R_factor_all 0.0383
_refine_ls_R_factor_gt 0.0319
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.0654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0794
_refine_ls_wR_factor_ref 0.0833
_reflns_number_gt 1349
_reflns_number_total 1505
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200155p_si_001.cif
_cod_data_source_block p212121
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1502049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.9669(3) 0.43907(18) 0.25361(7) 0.0638(4) Uani 1 1 d .
O2 O 0.8112(3) 0.52842(19) 0.06262(6) 0.0571(4) Uani 1 1 d .
O3 O 1.0505(3) 0.7501(2) 0.05216(8) 0.0816(6) Uani 1 1 d .
N1 N 0.6066(3) 0.40570(18) 0.18783(7) 0.0462(4) Uani 1 1 d .
N2 N 0.7443(3) 0.65819(19) 0.21068(7) 0.0486(4) Uani 1 1 d .
H2N H 0.8266 0.7357 0.2307 0.058 Uiso 1 1 calc R
C1 C 0.5414(3) 0.6904(2) 0.16302(9) 0.0431(4) Uani 1 1 d .
H1 H 0.3958 0.7483 0.1834 0.052 Uiso 1 1 calc R
C2 C 0.6427(4) 0.7877(2) 0.10479(10) 0.0511(4) Uani 1 1 d .
H2A H 0.5026 0.8098 0.0746 0.061 Uiso 1 1 calc R
H2B H 0.7111 0.8935 0.1195 0.061 Uiso 1 1 calc R
C3 C 0.8492(4) 0.6922(3) 0.07079(9) 0.0526(5) Uani 1 1 d .
C4 C 0.7900(3) 0.4971(2) 0.22019(8) 0.0443(4) Uani 1 1 d .
C5 C 0.6758(6) 0.2497(2) 0.15550(10) 0.0668(6) Uani 1 1 d .
H5A H 0.5858 0.1566 0.1752 0.080 Uiso 1 1 calc R
H5B H 0.8602 0.2299 0.1581 0.080 Uiso 1 1 calc R
C6 C 0.5911(7) 0.2746(3) 0.08459(11) 0.0814(8) Uani 1 1 d .
H6A H 0.7212 0.2326 0.0547 0.098 Uiso 1 1 calc R
H6B H 0.4300 0.2171 0.0762 0.098 Uiso 1 1 calc R
C7 C 0.5576(4) 0.4607(3) 0.07625(9) 0.0548(5) Uani 1 1 d .
H7 H 0.4328 0.4879 0.0419 0.066 Uiso 1 1 calc R
C8 C 0.4652(3) 0.5142(2) 0.14319(8) 0.0459(4) Uani 1 1 d .
H8 H 0.2786 0.4977 0.1476 0.055 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0720(9) 0.0601(9) 0.0592(8) 0.0086(7) -0.0184(8) 0.0121(7)
O2 0.0568(8) 0.0692(9) 0.0453(7) 0.0051(6) 0.0100(6) 0.0178(7)
O3 0.0409(7) 0.1336(17) 0.0704(9) 0.0354(11) 0.0028(7) -0.0123(9)
N1 0.0530(9) 0.0406(7) 0.0450(8) 0.0034(6) 0.0029(7) -0.0041(7)
N2 0.0548(9) 0.0436(8) 0.0475(8) -0.0039(6) -0.0116(7) 0.0030(7)
C1 0.0386(8) 0.0456(9) 0.0451(8) -0.0023(7) 0.0009(7) 0.0077(7)
C2 0.0480(9) 0.0467(10) 0.0584(10) 0.0086(9) -0.0078(9) 0.0012(8)
C3 0.0382(9) 0.0760(13) 0.0435(9) 0.0189(9) -0.0026(8) 0.0020(9)
C4 0.0498(10) 0.0469(10) 0.0363(8) 0.0027(7) 0.0020(7) 0.0033(8)
C5 0.0982(17) 0.0417(10) 0.0605(12) -0.0012(9) -0.0003(12) 0.0025(11)
C6 0.125(2) 0.0548(13) 0.0641(13) -0.0148(11) -0.0160(15) -0.0012(14)
C7 0.0637(11) 0.0548(11) 0.0459(9) -0.0041(8) -0.0101(9) -0.0004(9)
C8 0.0349(7) 0.0532(10) 0.0497(9) 0.0037(8) 0.0004(7) -0.0036(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O2 C7 118.56(16)
C4 N1 C8 109.21(14)
C4 N1 C5 120.49(17)
C8 N1 C5 110.70(15)
C4 N2 C1 113.54(15)
C4 N2 H2N 123.2
C1 N2 H2N 123.2
N2 C1 C2 111.52(15)
N2 C1 C8 101.49(14)
C2 C1 C8 111.09(15)
N2 C1 H1 110.8
C2 C1 H1 110.8
C8 C1 H1 110.8
C3 C2 C1 110.37(15)
C3 C2 H2A 109.6
C1 C2 H2A 109.6
C3 C2 H2B 109.6
C1 C2 H2B 109.6
H2A C2 H2B 108.1
O3 C3 O2 117.9(2)
O3 C3 C2 124.8(2)
O2 C3 C2 117.31(16)
O1 C4 N2 125.49(18)
O1 C4 N1 125.38(16)
N2 C4 N1 109.12(15)
N1 C5 C6 104.22(17)
N1 C5 H5A 110.9
C6 C5 H5A 110.9
N1 C5 H5B 110.9
C6 C5 H5B 110.9
H5A C5 H5B 108.9
C7 C6 C5 105.60(17)
C7 C6 H6A 110.6
C5 C6 H6A 110.6
C7 C6 H6B 110.6
C5 C6 H6B 110.6
H6A C6 H6B 108.8
O2 C7 C8 110.74(15)
O2 C7 C6 106.8(2)
C8 C7 C6 102.44(17)
O2 C7 H7 112.1
C8 C7 H7 112.1
C6 C7 H7 112.1
N1 C8 C7 103.68(14)
N1 C8 C1 105.02(14)
C7 C8 C1 115.00(15)
N1 C8 H8 110.9
C7 C8 H8 110.9
C1 C8 H8 110.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.235(2)
O2 C3 1.343(3)
O2 C7 1.450(3)
O3 C3 1.204(2)
N1 C4 1.372(2)
N1 C8 1.460(2)
N1 C5 1.464(2)
N2 C4 1.332(2)
N2 C1 1.457(2)
N2 H2N 0.8600
C1 C2 1.519(3)
C1 C8 1.527(2)
C1 H1 0.9800
C2 C3 1.490(3)
C2 H2A 0.9700
C2 H2B 0.9700
C5 C6 1.528(3)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.517(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.513(3)
C7 H7 0.9800
C8 H8 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.86 1.98 2.807(2) 160.8 3_755
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 N2 C1 C2 -118.58(18)
C4 N2 C1 C8 -0.2(2)
N2 C1 C2 C3 60.8(2)
C8 C1 C2 C3 -51.7(2)
C7 O2 C3 O3 -171.52(15)
C7 O2 C3 C2 10.9(2)
C1 C2 C3 O3 -135.40(19)
C1 C2 C3 O2 42.0(2)
C1 N2 C4 O1 173.26(17)
C1 N2 C4 N1 -7.8(2)
C8 N1 C4 O1 -168.25(17)
C5 N1 C4 O1 -38.5(3)
C8 N1 C4 N2 12.8(2)
C5 N1 C4 N2 142.55(17)
C4 N1 C5 C6 -123.6(2)
C8 N1 C5 C6 5.5(3)
N1 C5 C6 C7 17.6(3)
C3 O2 C7 C8 -51.2(2)
C3 O2 C7 C6 -161.99(16)
C5 C6 C7 O2 83.4(2)
C5 C6 C7 C8 -33.1(3)
C4 N1 C8 C7 108.52(16)
C5 N1 C8 C7 -26.4(2)
C4 N1 C8 C1 -12.53(18)
C5 N1 C8 C1 -147.44(17)
O2 C7 C8 N1 -77.69(18)
C6 C7 C8 N1 35.9(2)
O2 C7 C8 C1 36.4(2)
C6 C7 C8 C1 149.96(18)
N2 C1 C8 N1 7.49(17)
C2 C1 C8 N1 126.15(15)
N2 C1 C8 C7 -105.80(17)
C2 C1 C8 C7 12.9(2)
|
1502050.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502050.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502050
loop_
_publ_author_name
'Hovey, M. Todd'
'Eklund, Emily J.'
'Pike, Robert D.'
'Mainkar, Anshul A.'
'Scheerer, Jonathan R.'
_publ_section_title
;
Synthesis of (+-)-acetylnorloline via stereoselective tethered
aminohydroxylation.
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1246
_journal_page_last 1249
_journal_paper_doi 10.1021/ol200155p
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C23 H32 N2 O12 S2'
_chemical_formula_sum 'C23 H32 N2 O12 S2'
_chemical_formula_weight 592.63
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 97.5800(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 21.3138(6)
_cell_length_b 9.4146(3)
_cell_length_c 13.7762(4)
_cell_measurement_reflns_used 9865
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 68.08
_cell_measurement_theta_min 4.18
_cell_volume 2740.19(14)
_computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)'
_computing_data_collection 'APEX2 (Bruker AXS, 2004)'
_computing_data_reduction SAINTPLUS
_computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)'
_computing_publication_material 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement 'XSHELL (Bruker, 2004)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type 'Bruker SMART APEX II CCD'
_diffrn_measurement_method '\w and \y'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0272
_diffrn_reflns_av_sigmaI/netI 0.0168
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 29210
_diffrn_reflns_theta_full 67.00
_diffrn_reflns_theta_max 67.00
_diffrn_reflns_theta_min 2.09
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 2.339
_exptl_absorpt_correction_T_max 0.8821
_exptl_absorpt_correction_T_min 0.4831
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.437
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 1248
_exptl_crystal_size_max 0.36
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.06
_refine_diff_density_max 0.681
_refine_diff_density_min -0.617
_refine_diff_density_rms 0.052
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 357
_refine_ls_number_reflns 4855
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.042
_refine_ls_R_factor_all 0.0436
_refine_ls_R_factor_gt 0.0389
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+3.0954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0977
_refine_ls_wR_factor_ref 0.1011
_reflns_number_gt 4338
_reflns_number_total 4855
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200155p_si_002.cif
_cod_data_source_block p21onc
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502050
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.03756(2) 0.55846(6) 0.23495(3) 0.02304(13) Uani 1 1 d .
S2 S 0.13477(2) 0.71848(5) 0.51261(3) 0.02206(13) Uani 1 1 d .
O1 O 0.12526(7) 0.18800(15) 0.16706(10) 0.0256(3) Uani 1 1 d .
O2 O 0.13323(8) 0.25947(18) 0.01880(10) 0.0336(4) Uani 1 1 d .
O3 O 0.23628(8) 0.4063(2) 0.00010(11) 0.0387(4) Uani 1 1 d .
O4 O 0.27077(7) 0.53367(15) 0.13350(10) 0.0267(3) Uani 1 1 d .
O5 O 0.35438(8) 0.10959(18) 0.37831(14) 0.0434(4) Uani 1 1 d .
O6 O 0.31459(7) 0.33101(16) 0.39851(12) 0.0317(4) Uani 1 1 d .
O7 O 0.09811(6) 0.46583(15) 0.27250(11) 0.0257(3) Uani 1 1 d .
O8 O -0.00345(7) 0.54723(19) 0.30799(11) 0.0347(4) Uani 1 1 d .
O9 O 0.05682(7) 0.69615(16) 0.20809(11) 0.0312(4) Uani 1 1 d .
O10 O 0.14603(7) 0.69292(15) 0.40233(10) 0.0251(3) Uani 1 1 d .
O11 O 0.18983(7) 0.67330(17) 0.57616(10) 0.0306(3) Uani 1 1 d .
O12 O 0.11581(7) 0.86365(15) 0.51437(10) 0.0273(3) Uani 1 1 d .
N1 N 0.19601(8) 0.37017(17) 0.14571(11) 0.0194(3) Uani 1 1 d .
N2 N 0.25684(8) 0.17481(18) 0.30336(12) 0.0222(4) Uani 1 1 d .
C1 C 0.20535(9) 0.4026(2) 0.25175(13) 0.0182(4) Uani 1 1 d .
H1 H 0.2497 0.4383 0.2677 0.022 Uiso 1 1 calc R
C2 C 0.16180(9) 0.5214(2) 0.27855(14) 0.0196(4) Uani 1 1 d .
H2 H 0.1630 0.6032 0.2326 0.023 Uiso 1 1 calc R
C3 C 0.18281(12) 0.5690(3) 0.38289(17) 0.0358(6) Uani 1 1 d .
H3A H 0.1760 0.4918 0.4291 0.043 Uiso 1 1 calc R
H3B H 0.2285 0.5928 0.3914 0.043 Uiso 1 1 calc R
C4 C 0.15087(10) 0.2717(2) 0.10513(14) 0.0225(4) Uani 1 1 d .
C5 C 0.23756(11) 0.0281(2) 0.27606(16) 0.0274(5) Uani 1 1 d .
H5A H 0.2629 -0.0416 0.3185 0.033 Uiso 1 1 calc R
H5B H 0.2425 0.0085 0.2069 0.033 Uiso 1 1 calc R
C6 C 0.16807(10) 0.0225(2) 0.29159(15) 0.0263(5) Uani 1 1 d .
H6A H 0.1442 -0.0447 0.2454 0.032 Uiso 1 1 calc R
H6B H 0.1636 -0.0065 0.3594 0.032 Uiso 1 1 calc R
C7 C 0.14522(10) 0.1734(2) 0.27192(14) 0.0212(4) Uani 1 1 d .
H7 H 0.1089 0.1940 0.3089 0.025 Uiso 1 1 calc R
C8 C 0.20131(9) 0.2658(2) 0.30966(14) 0.0189(4) Uani 1 1 d .
H8 H 0.1992 0.2899 0.3799 0.023 Uiso 1 1 calc R
C9 C 0.23457(10) 0.4357(2) 0.08392(14) 0.0234(4) Uani 1 1 d .
C10 C 0.31562(11) 0.6054(3) 0.07802(17) 0.0336(5) Uani 1 1 d .
H10A H 0.2948 0.6862 0.0406 0.040 Uiso 1 1 calc R
H10B H 0.3315 0.5386 0.0314 0.040 Uiso 1 1 calc R
C11 C 0.36891(10) 0.6572(2) 0.15036(18) 0.0310(5) Uani 1 1 d .
C12 C 0.35897(12) 0.7629(3) 0.21643(19) 0.0388(6) Uani 1 1 d .
H12 H 0.3178 0.8025 0.2146 0.047 Uiso 1 1 calc R
C13 C 0.40689(14) 0.8124(3) 0.2847(2) 0.0532(7) Uani 1 1 d .
H13 H 0.3989 0.8849 0.3295 0.064 Uiso 1 1 calc R
C14 C 0.46613(15) 0.7556(3) 0.2873(3) 0.0704(11) Uani 1 1 d .
H14 H 0.4994 0.7883 0.3348 0.085 Uiso 1 1 calc R
C15 C 0.47814(14) 0.6517(4) 0.2220(4) 0.0811(13) Uani 1 1 d .
H15 H 0.5196 0.6140 0.2237 0.097 Uiso 1 1 calc R
C16 C 0.42913(13) 0.6017(3) 0.1529(3) 0.0599(9) Uani 1 1 d .
H16 H 0.4372 0.5298 0.1078 0.072 Uiso 1 1 calc R
C17 C 0.31244(10) 0.1971(2) 0.36258(17) 0.0303(5) Uani 1 1 d .
C18 C 0.36874(14) 0.3806(3) 0.4679(3) 0.0600(9) Uani 1 1 d .
C19 C 0.42897(16) 0.3674(5) 0.4237(5) 0.133(3) Uani 1 1 d .
H19A H 0.4406 0.2670 0.4206 0.200 Uiso 1 1 calc R
H19B H 0.4628 0.4192 0.4641 0.200 Uiso 1 1 calc R
H19C H 0.4230 0.4074 0.3574 0.200 Uiso 1 1 calc R
C20 C 0.3674(2) 0.2998(4) 0.5657(3) 0.1042(19) Uani 1 1 d .
H20A H 0.3243 0.3016 0.5834 0.156 Uiso 1 1 calc R
H20B H 0.3964 0.3456 0.6174 0.156 Uiso 1 1 calc R
H20C H 0.3805 0.2011 0.5580 0.156 Uiso 1 1 calc R
C21 C 0.35333(14) 0.5353(3) 0.4823(2) 0.0537(8) Uani 1 1 d .
H21A H 0.3472 0.5834 0.4187 0.081 Uiso 1 1 calc R
H21B H 0.3883 0.5802 0.5247 0.081 Uiso 1 1 calc R
H21C H 0.3145 0.5424 0.5129 0.081 Uiso 1 1 calc R
C22 C 0.00604(12) 0.4607(3) 0.13229(16) 0.0364(6) Uani 1 1 d .
H22A H -0.0343 0.5030 0.1039 0.055 Uiso 1 1 calc R
H22B H -0.0011 0.3625 0.1517 0.055 Uiso 1 1 calc R
H22C H 0.0357 0.4619 0.0837 0.055 Uiso 1 1 calc R
C23 C 0.07138(11) 0.6057(2) 0.52600(16) 0.0279(5) Uani 1 1 d .
H23A H 0.0590 0.6176 0.5915 0.042 Uiso 1 1 calc R
H23B H 0.0841 0.5069 0.5174 0.042 Uiso 1 1 calc R
H23C H 0.0355 0.6292 0.4766 0.042 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0216(2) 0.0279(3) 0.0193(2) 0.0001(2) 0.00140(18) 0.00301(19)
S2 0.0298(3) 0.0184(2) 0.0178(2) -0.00114(18) 0.00271(19) -0.00086(19)
O1 0.0303(8) 0.0273(8) 0.0183(7) 0.0021(6) -0.0004(6) -0.0089(6)
O2 0.0418(9) 0.0406(9) 0.0177(7) -0.0034(7) 0.0007(6) -0.0127(7)
O3 0.0449(10) 0.0532(11) 0.0202(8) -0.0044(7) 0.0122(7) -0.0156(8)
O4 0.0302(8) 0.0266(8) 0.0248(7) 0.0004(6) 0.0095(6) -0.0093(6)
O5 0.0303(9) 0.0355(9) 0.0611(11) -0.0026(9) -0.0060(8) 0.0107(7)
O6 0.0274(8) 0.0258(8) 0.0381(8) -0.0026(7) -0.0094(7) 0.0004(6)
O7 0.0198(7) 0.0206(7) 0.0372(8) 0.0048(6) 0.0058(6) 0.0003(6)
O8 0.0264(8) 0.0544(11) 0.0240(7) 0.0041(7) 0.0064(6) 0.0093(7)
O9 0.0378(9) 0.0252(8) 0.0292(8) 0.0043(6) -0.0008(7) 0.0053(7)
O10 0.0321(8) 0.0226(7) 0.0208(7) -0.0020(6) 0.0043(6) 0.0061(6)
O11 0.0345(8) 0.0319(8) 0.0235(7) -0.0016(6) -0.0030(6) 0.0011(7)
O12 0.0404(9) 0.0182(7) 0.0244(7) -0.0017(6) 0.0085(6) 0.0005(6)
N1 0.0231(8) 0.0215(8) 0.0140(7) 0.0003(6) 0.0038(6) -0.0017(7)
N2 0.0250(9) 0.0201(8) 0.0214(8) -0.0009(7) 0.0031(7) 0.0030(7)
C1 0.0210(10) 0.0199(10) 0.0141(9) -0.0012(7) 0.0036(7) -0.0012(8)
C2 0.0185(9) 0.0201(10) 0.0204(9) 0.0001(8) 0.0038(7) -0.0015(8)
C3 0.0371(13) 0.0379(13) 0.0302(12) -0.0135(10) -0.0034(10) 0.0173(10)
C4 0.0257(10) 0.0230(10) 0.0191(10) -0.0021(8) 0.0034(8) -0.0008(8)
C5 0.0356(12) 0.0220(11) 0.0243(10) -0.0046(9) 0.0026(9) 0.0042(9)
C6 0.0360(12) 0.0193(10) 0.0234(10) -0.0002(8) 0.0030(9) -0.0023(9)
C7 0.0269(10) 0.0215(10) 0.0156(9) 0.0008(8) 0.0046(8) -0.0030(8)
C8 0.0222(10) 0.0194(10) 0.0155(9) 0.0004(8) 0.0035(7) 0.0007(8)
C9 0.0250(10) 0.0264(11) 0.0192(10) 0.0014(8) 0.0042(8) -0.0011(8)
C10 0.0359(12) 0.0337(12) 0.0341(12) 0.0038(10) 0.0151(10) -0.0098(10)
C11 0.0267(11) 0.0206(11) 0.0477(13) 0.0011(10) 0.0121(10) -0.0039(8)
C12 0.0356(13) 0.0330(13) 0.0491(15) -0.0033(11) 0.0103(11) 0.0017(10)
C13 0.0552(17) 0.0358(14) 0.0676(19) -0.0129(14) 0.0049(15) -0.0062(13)
C14 0.0456(17) 0.0393(16) 0.119(3) -0.0150(18) -0.0166(19) -0.0108(13)
C15 0.0281(14) 0.0503(19) 0.159(4) -0.025(2) -0.0077(19) 0.0030(13)
C16 0.0330(14) 0.0313(14) 0.117(3) -0.0235(16) 0.0177(16) -0.0020(11)
C17 0.0271(11) 0.0298(12) 0.0330(12) 0.0014(10) 0.0003(9) 0.0026(9)
C18 0.0405(15) 0.0393(15) 0.088(2) -0.0142(15) -0.0359(15) 0.0014(12)
C19 0.0281(17) 0.095(3) 0.271(7) -0.088(4) -0.002(3) -0.0098(19)
C20 0.151(4) 0.047(2) 0.087(3) -0.0033(19) -0.089(3) 0.003(2)
C21 0.0481(16) 0.0355(15) 0.0683(19) -0.0093(14) -0.0265(14) -0.0048(12)
C22 0.0401(13) 0.0457(15) 0.0220(10) -0.0027(10) -0.0011(10) -0.0105(11)
C23 0.0362(12) 0.0220(10) 0.0254(10) 0.0006(9) 0.0037(9) -0.0060(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O8 S1 O9 118.50(10)
O8 S1 O7 106.14(9)
O9 S1 O7 109.59(8)
O8 S1 C22 109.11(11)
O9 S1 C22 111.27(11)
O7 S1 C22 100.60(11)
O12 S2 O11 119.02(9)
O12 S2 O10 103.91(8)
O11 S2 O10 108.94(8)
O12 S2 C23 110.85(10)
O11 S2 C23 109.72(10)
O10 S2 C23 103.03(9)
C4 O1 C7 126.92(15)
C9 O4 C10 115.19(16)
C17 O6 C18 121.22(18)
C2 O7 S1 122.46(12)
C3 O10 S2 116.91(13)
C4 N1 C9 118.45(16)
C4 N1 C1 121.81(15)
C9 N1 C1 119.70(16)
C17 N2 C8 121.11(17)
C17 N2 C5 119.18(17)
C8 N2 C5 111.15(16)
N1 C1 C8 109.48(15)
N1 C1 C2 112.46(15)
C8 C1 C2 114.43(15)
N1 C1 H1 106.7
C8 C1 H1 106.7
C2 C1 H1 106.7
O7 C2 C3 108.61(17)
O7 C2 C1 108.45(15)
C3 C2 C1 109.43(16)
O7 C2 H2 110.1
C3 C2 H2 110.1
C1 C2 H2 110.1
O10 C3 C2 108.30(17)
O10 C3 H3A 110.0
C2 C3 H3A 110.0
O10 C3 H3B 110.0
C2 C3 H3B 110.0
H3A C3 H3B 108.4
O2 C4 O1 118.40(18)
O2 C4 N1 124.52(19)
O1 C4 N1 117.07(16)
N2 C5 C6 103.85(16)
N2 C5 H5A 111.0
C6 C5 H5A 111.0
N2 C5 H5B 111.0
C6 C5 H5B 111.0
H5A C5 H5B 109.0
C7 C6 C5 103.75(17)
C7 C6 H6A 111.0
C5 C6 H6A 111.0
C7 C6 H6B 111.0
C5 C6 H6B 111.0
H6A C6 H6B 109.0
O1 C7 C8 113.58(15)
O1 C7 C6 108.10(16)
C8 C7 C6 104.90(16)
O1 C7 H7 110.0
C8 C7 H7 110.0
C6 C7 H7 110.0
N2 C8 C7 104.44(15)
N2 C8 C1 111.07(15)
C7 C8 C1 113.74(16)
N2 C8 H8 109.1
C7 C8 H8 109.1
C1 C8 H8 109.1
O3 C9 O4 124.57(19)
O3 C9 N1 125.54(19)
O4 C9 N1 109.86(16)
O4 C10 C11 107.10(18)
O4 C10 H10A 110.3
C11 C10 H10A 110.3
O4 C10 H10B 110.3
C11 C10 H10B 110.3
H10A C10 H10B 108.5
C16 C11 C12 118.5(2)
C16 C11 C10 121.1(2)
C12 C11 C10 120.4(2)
C13 C12 C11 122.0(2)
C13 C12 H12 119.0
C11 C12 H12 119.0
C14 C13 C12 119.0(3)
C14 C13 H13 120.5
C12 C13 H13 120.5
C13 C14 C15 120.8(3)
C13 C14 H14 119.6
C15 C14 H14 119.6
C14 C15 C16 119.8(3)
C14 C15 H15 120.1
C16 C15 H15 120.1
C11 C16 C15 119.9(3)
C11 C16 H16 120.1
C15 C16 H16 120.1
O5 C17 O6 125.3(2)
O5 C17 N2 124.3(2)
O6 C17 N2 110.33(18)
O6 C18 C19 110.5(3)
O6 C18 C21 103.0(2)
C19 C18 C21 110.3(3)
O6 C18 C20 107.8(3)
C19 C18 C20 115.3(4)
C21 C18 C20 109.2(3)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
S1 C22 H22A 109.5
S1 C22 H22B 109.5
H22A C22 H22B 109.5
S1 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
S2 C23 H23A 109.5
S2 C23 H23B 109.5
H23A C23 H23B 109.5
S2 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O8 1.4211(16)
S1 O9 1.4234(16)
S1 O7 1.5867(14)
S1 C22 1.746(2)
S2 O12 1.4264(15)
S2 O11 1.4330(16)
S2 O10 1.5874(14)
S2 C23 1.747(2)
O1 C4 1.330(2)
O1 C7 1.458(2)
O2 C4 1.205(2)
O3 C9 1.192(2)
O4 C9 1.332(3)
O4 C10 1.465(2)
O5 C17 1.214(3)
O6 C17 1.353(3)
O6 C18 1.474(3)
O7 C2 1.447(2)
O10 C3 1.450(3)
N1 C4 1.399(3)
N1 C9 1.402(3)
N1 C1 1.480(2)
N2 C17 1.363(3)
N2 C8 1.473(2)
N2 C5 1.476(3)
C1 C8 1.523(3)
C1 C2 1.530(3)
C1 H1 1.0000
C2 C3 1.516(3)
C2 H2 1.0000
C3 H3A 0.9900
C3 H3B 0.9900
C5 C6 1.525(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.515(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.514(3)
C7 H7 1.0000
C8 H8 1.0000
C10 C11 1.491(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C16 1.382(3)
C11 C12 1.383(3)
C12 C13 1.375(4)
C12 H12 0.9500
C13 C14 1.367(4)
C13 H13 0.9500
C14 C15 1.377(5)
C14 H14 0.9500
C15 C16 1.398(5)
C15 H15 0.9500
C16 H16 0.9500
C18 C19 1.497(6)
C18 C21 1.511(4)
C18 C20 1.551(6)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O8 S1 O7 C2 -127.81(15)
O9 S1 O7 C2 1.26(17)
C22 S1 O7 C2 118.54(16)
O12 S2 O10 C3 162.71(16)
O11 S2 O10 C3 34.87(18)
C23 S2 O10 C3 -81.59(17)
C4 N1 C1 C8 40.4(2)
C9 N1 C1 C8 -137.42(18)
C4 N1 C1 C2 -88.0(2)
C9 N1 C1 C2 94.2(2)
S1 O7 C2 C3 97.25(18)
S1 O7 C2 C1 -143.91(13)
N1 C1 C2 O7 73.07(19)
C8 C1 C2 O7 -52.7(2)
N1 C1 C2 C3 -168.61(18)
C8 C1 C2 C3 65.6(2)
S2 O10 C3 C2 151.95(15)
O7 C2 C3 O10 -68.8(2)
C1 C2 C3 O10 172.95(17)
C7 O1 C4 O2 171.81(19)
C7 O1 C4 N1 -9.3(3)
C9 N1 C4 O2 -16.2(3)
C1 N1 C4 O2 166.0(2)
C9 N1 C4 O1 165.02(17)
C1 N1 C4 O1 -12.8(3)
C17 N2 C5 C6 133.93(19)
C8 N2 C5 C6 -14.3(2)
N2 C5 C6 C7 29.9(2)
C4 O1 C7 C8 -0.1(3)
C4 O1 C7 C6 -116.1(2)
C5 C6 C7 O1 86.62(18)
C5 C6 C7 C8 -34.87(19)
C17 N2 C8 C7 -154.71(18)
C5 N2 C8 C7 -7.1(2)
C17 N2 C8 C1 82.3(2)
C5 N2 C8 C1 -130.14(17)
O1 C7 C8 N2 -91.83(18)
C6 C7 C8 N2 26.00(19)
O1 C7 C8 C1 29.4(2)
C6 C7 C8 C1 147.25(16)
N1 C1 C8 N2 70.52(19)
C2 C1 C8 N2 -162.20(15)
N1 C1 C8 C7 -47.0(2)
C2 C1 C8 C7 80.3(2)
C10 O4 C9 O3 -1.0(3)
C10 O4 C9 N1 177.22(17)
C4 N1 C9 O3 -6.8(3)
C1 N1 C9 O3 171.1(2)
C4 N1 C9 O4 175.02(17)
C1 N1 C9 O4 -7.1(2)
C9 O4 C10 C11 -154.86(18)
O4 C10 C11 C16 113.6(3)
O4 C10 C11 C12 -66.6(3)
C16 C11 C12 C13 -0.8(4)
C10 C11 C12 C13 179.4(2)
C11 C12 C13 C14 0.1(5)
C12 C13 C14 C15 0.8(6)
C13 C14 C15 C16 -1.0(6)
C12 C11 C16 C15 0.6(5)
C10 C11 C16 C15 -179.6(3)
C14 C15 C16 C11 0.2(6)
C18 O6 C17 O5 -4.2(4)
C18 O6 C17 N2 177.5(2)
C8 N2 C17 O5 161.7(2)
C5 N2 C17 O5 16.7(3)
C8 N2 C17 O6 -20.0(3)
C5 N2 C17 O6 -165.04(18)
C17 O6 C18 C19 58.5(4)
C17 O6 C18 C21 176.3(2)
C17 O6 C18 C20 -68.3(3)
|
1502051.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502051.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502051
loop_
_publ_author_name
'Liu, Xiaodong'
'Deng, Leijiao'
'Song, Hongjin'
'Jia, Huazhen'
'Wang, Rui'
_publ_section_title
;
Asymmetric aza-Mannich addition: synthesis of modified chiral
2-(ethylthio)-thiazolone derivatives with anticancer potency.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1494
_journal_page_last 1497
_journal_paper_doi 10.1021/ol200185h
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration none
_chemical_formula_sum 'C22 H25 Br N2 O3 S3'
_chemical_formula_weight 541.53
_chemical_name_systematic
;
?
;
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.7364(15)
_cell_length_b 13.139(3)
_cell_length_c 24.286(5)
_cell_measurement_reflns_used 4084
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 20.50
_cell_measurement_theta_min 2.76
_cell_volume 2468.6(9)
_computing_cell_refinement 'Bruker SAINT'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0507
_diffrn_reflns_av_sigmaI/netI 0.0686
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_number 18012
_diffrn_reflns_theta_full 25.50
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_min 2.28
_exptl_absorpt_coefficient_mu 1.945
_exptl_absorpt_correction_T_max 0.6120
_exptl_absorpt_correction_T_min 0.5750
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details SADABS
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.457
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 1112
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.28
_refine_diff_density_max 0.255
_refine_diff_density_min -0.333
_refine_diff_density_rms 0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.003(8)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 284
_refine_ls_number_reflns 4611
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.036
_refine_ls_R_factor_all 0.0645
_refine_ls_R_factor_gt 0.0386
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.4383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0737
_refine_ls_wR_factor_ref 0.0827
_reflns_number_gt 3496
_reflns_number_total 4611
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200185h_si_002.cif
_cod_data_source_block p212121
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2468.6(8)
_cod_original_sg_symbol_H-M P2(1)2(1)2(1)
_cod_database_code 1502051
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.20976(5) 1.11179(3) 0.154679(19) 0.06098(15) Uani 1 1 d .
C1 C 0.4381(5) 1.0679(3) 0.13587(14) 0.0378(9) Uani 1 1 d .
C2 C 0.5651(5) 1.1415(3) 0.13794(15) 0.0496(10) Uani 1 1 d .
H2 H 0.5396 1.2067 0.1504 0.060 Uiso 1 1 calc R
C3 C 0.7311(5) 1.1169(3) 0.12129(16) 0.0519(10) Uani 1 1 d .
H3 H 0.8177 1.1660 0.1220 0.062 Uiso 1 1 calc R
C4 C 0.7676(5) 1.0203(3) 0.10375(14) 0.0464(10) Uani 1 1 d .
H4 H 0.8790 1.0036 0.0926 0.056 Uiso 1 1 calc R
C5 C 0.6397(4) 0.9478(3) 0.10262(14) 0.0389(9) Uani 1 1 d .
H5 H 0.6668 0.8824 0.0908 0.047 Uiso 1 1 calc R
C6 C 0.4703(5) 0.9693(3) 0.11862(13) 0.0339(8) Uani 1 1 d .
C7 C 0.3299(4) 0.8883(3) 0.11621(13) 0.0361(8) Uani 1 1 d .
H7 H 0.2187 0.9241 0.1158 0.043 Uiso 1 1 calc R
C8 C 0.3300(4) 0.8177(3) 0.16840(14) 0.0355(8) Uani 1 1 d .
C9 C 0.5066(5) 0.7650(3) 0.17308(15) 0.0422(9) Uani 1 1 d .
C10 C 0.4294(5) 0.8827(3) 0.24873(14) 0.0478(10) Uani 1 1 d .
C11 C 0.1856(5) 0.7357(3) 0.16662(15) 0.0453(9) Uani 1 1 d .
H11 H 0.2140 0.6891 0.1365 0.054 Uiso 1 1 calc R
C12 C 0.0097(5) 0.7800(3) 0.1541(2) 0.0621(12) Uani 1 1 d .
H12A H -0.0200 0.8291 0.1818 0.093 Uiso 1 1 calc R
H12B H -0.0749 0.7265 0.1538 0.093 Uiso 1 1 calc R
H12C H 0.0122 0.8125 0.1187 0.093 Uiso 1 1 calc R
C13 C 0.1857(6) 0.6726(3) 0.22018(16) 0.0645(12) Uani 1 1 d .
H13A H 0.1499 0.7147 0.2504 0.097 Uiso 1 1 calc R
H13B H 0.3001 0.6473 0.2271 0.097 Uiso 1 1 calc R
H13C H 0.1072 0.6164 0.2164 0.097 Uiso 1 1 calc R
C14 C 0.2240(7) 0.9986(3) 0.31603(19) 0.0762(14) Uani 1 1 d .
H14A H 0.2222 1.0521 0.3435 0.091 Uiso 1 1 calc R
H14B H 0.1909 1.0287 0.2811 0.091 Uiso 1 1 calc R
C15 C 0.0947(8) 0.9210(4) 0.3311(2) 0.106(2) Uani 1 1 d .
H15A H 0.1398 0.8790 0.3601 0.158 Uiso 1 1 calc R
H15B H 0.0693 0.8795 0.2996 0.158 Uiso 1 1 calc R
H15C H -0.0091 0.9538 0.3435 0.158 Uiso 1 1 calc R
C16 C 0.4134(6) 1.0567(3) -0.00938(15) 0.0571(12) Uani 1 1 d .
H16 H 0.3120 1.0854 0.0041 0.068 Uiso 1 1 calc R
C17 C 0.5529(7) 1.1179(3) -0.02225(17) 0.0664(13) Uani 1 1 d .
H17 H 0.5442 1.1880 -0.0174 0.080 Uiso 1 1 calc R
C18 C 0.7038(7) 1.0773(3) -0.04209(16) 0.0588(12) Uani 1 1 d .
C19 C 0.7131(6) 0.9736(3) -0.05030(15) 0.0542(10) Uani 1 1 d .
H19 H 0.8137 0.9451 -0.0645 0.065 Uiso 1 1 calc R
C20 C 0.5763(5) 0.9123(3) -0.03783(15) 0.0491(10) Uani 1 1 d .
H20 H 0.5850 0.8426 -0.0437 0.059 Uiso 1 1 calc R
C21 C 0.4256(5) 0.9520(3) -0.01669(13) 0.0420(10) Uani 1 1 d .
C22 C 0.8593(8) 1.1447(4) -0.0528(2) 0.107(2) Uani 1 1 d .
H22A H 0.8992 1.1344 -0.0898 0.160 Uiso 1 1 calc R
H22B H 0.9499 1.1276 -0.0274 0.160 Uiso 1 1 calc R
H22C H 0.8272 1.2147 -0.0479 0.160 Uiso 1 1 calc R
N1 N 0.3358(4) 0.8245(2) 0.06631(11) 0.0406(8) Uani 1 1 d .
H1 H 0.3761 0.7636 0.0680 0.049 Uiso 1 1 calc R
N2 N 0.3037(4) 0.8835(2) 0.21580(10) 0.0387(7) Uani 1 1 d .
O1 O 0.5611(4) 0.7031(2) 0.14122(11) 0.0598(8) Uani 1 1 d .
O2 O 0.1150(4) 0.9290(3) 0.02015(12) 0.0792(10) Uani 1 1 d .
O3 O 0.2563(5) 0.7842(2) -0.02828(10) 0.0788(10) Uani 1 1 d .
S1 S 0.61261(15) 0.80697(10) 0.23373(5) 0.0647(3) Uani 1 1 d .
S2 S 0.44190(19) 0.95074(11) 0.31021(5) 0.0763(4) Uani 1 1 d .
S3 S 0.26530(14) 0.87007(9) 0.00775(4) 0.0531(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0467(2) 0.0508(2) 0.0854(3) -0.0117(2) 0.0012(2) 0.0108(2)
C1 0.035(2) 0.042(2) 0.037(2) -0.0044(17) -0.0043(16) 0.0052(18)
C2 0.057(3) 0.034(2) 0.058(2) -0.0061(18) -0.010(2) -0.0032(19)
C3 0.041(2) 0.049(3) 0.066(2) -0.004(2) -0.0064(19) -0.012(2)
C4 0.031(2) 0.055(3) 0.053(2) 0.0012(19) -0.0001(18) -0.005(2)
C5 0.036(2) 0.040(2) 0.041(2) 0.0010(17) -0.0005(16) 0.0059(18)
C6 0.038(2) 0.035(2) 0.0278(17) 0.0020(16) -0.0058(16) -0.0034(17)
C7 0.035(2) 0.0373(19) 0.0362(18) -0.0023(18) -0.0038(14) 0.0011(18)
C8 0.0311(19) 0.039(2) 0.0363(19) -0.0008(17) 0.0008(15) -0.0002(15)
C9 0.045(2) 0.042(2) 0.039(2) 0.0119(19) 0.0108(18) 0.0030(19)
C10 0.052(2) 0.054(2) 0.038(2) 0.007(2) 0.0029(19) -0.006(2)
C11 0.047(2) 0.044(2) 0.045(2) -0.0073(18) 0.0071(19) -0.0082(19)
C12 0.036(2) 0.069(3) 0.081(3) 0.002(3) 0.000(2) -0.014(2)
C13 0.076(3) 0.056(3) 0.061(3) 0.010(2) 0.007(3) -0.019(3)
C14 0.100(4) 0.064(3) 0.064(3) -0.016(2) 0.010(3) 0.004(3)
C15 0.133(5) 0.087(4) 0.097(4) -0.011(3) 0.061(4) -0.004(4)
C16 0.071(3) 0.053(3) 0.047(2) -0.001(2) 0.008(2) 0.020(3)
C17 0.105(4) 0.031(2) 0.063(3) 0.001(2) 0.013(3) -0.001(3)
C18 0.082(3) 0.052(3) 0.042(2) -0.0069(19) 0.014(2) -0.020(3)
C19 0.064(3) 0.052(3) 0.047(2) -0.0070(19) 0.011(2) 0.006(3)
C20 0.061(3) 0.037(2) 0.050(2) -0.0015(18) 0.002(2) 0.000(2)
C21 0.056(3) 0.044(3) 0.0258(19) 0.0001(17) -0.0020(18) 0.005(2)
C22 0.125(5) 0.096(5) 0.099(4) -0.019(3) 0.034(4) -0.054(4)
N1 0.057(2) 0.0302(17) 0.0341(16) -0.0041(13) -0.0042(14) -0.0086(15)
N2 0.0428(17) 0.0395(16) 0.0337(15) -0.0020(14) 0.0038(14) -0.0023(18)
O1 0.0647(19) 0.0532(18) 0.0614(18) 0.0052(15) 0.0180(16) 0.0170(16)
O2 0.0391(17) 0.137(3) 0.0613(19) 0.0161(18) -0.0049(14) 0.011(2)
O3 0.111(3) 0.086(2) 0.0395(14) -0.0149(15) -0.0071(17) -0.041(2)
S1 0.0446(6) 0.0960(9) 0.0535(6) 0.0099(6) -0.0061(5) 0.0133(7)
S2 0.0932(10) 0.0883(10) 0.0473(6) -0.0172(6) -0.0153(7) -0.0076(8)
S3 0.0544(7) 0.0680(8) 0.0368(5) 0.0010(5) -0.0079(5) -0.0149(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 122.6(3)
C2 C1 Br1 116.0(3)
C6 C1 Br1 121.4(3)
C1 C2 C3 119.1(3)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 119.9(4)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.0(4)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 122.1(3)
C4 C5 H5 119.0
C6 C5 H5 119.0
C1 C6 C5 116.2(3)
C1 C6 C7 122.5(3)
C5 C6 C7 121.2(3)
N1 C7 C6 114.0(3)
N1 C7 C8 109.1(3)
C6 C7 C8 112.4(3)
N1 C7 H7 107.0
C6 C7 H7 107.0
C8 C7 H7 107.0
N2 C8 C9 109.5(3)
N2 C8 C11 109.5(3)
C9 C8 C11 109.2(3)
N2 C8 C7 106.7(3)
C9 C8 C7 109.0(3)
C11 C8 C7 112.8(3)
O1 C9 C8 124.8(4)
O1 C9 S1 125.8(3)
C8 C9 S1 109.4(3)
N2 C10 S2 125.6(3)
N2 C10 S1 119.5(3)
S2 C10 S1 114.9(2)
C12 C11 C13 112.2(3)
C12 C11 C8 112.7(3)
C13 C11 C8 110.4(3)
C12 C11 H11 107.0
C13 C11 H11 107.0
C8 C11 H11 107.0
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 S2 114.3(4)
C15 C14 H14A 108.7
S2 C14 H14A 108.7
C15 C14 H14B 108.7
S2 C14 H14B 108.7
H14A C14 H14B 107.6
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 C21 119.6(4)
C17 C16 H16 120.2
C21 C16 H16 120.2
C18 C17 C16 121.2(4)
C18 C17 H17 119.4
C16 C17 H17 119.4
C17 C18 C19 118.7(4)
C17 C18 C22 120.6(4)
C19 C18 C22 120.7(5)
C20 C19 C18 120.7(4)
C20 C19 H19 119.6
C18 C19 H19 119.6
C19 C20 C21 121.1(4)
C19 C20 H20 119.4
C21 C20 H20 119.4
C20 C21 C16 118.7(4)
C20 C21 S3 119.7(3)
C16 C21 S3 121.2(3)
C18 C22 H22A 109.5
C18 C22 H22B 109.5
H22A C22 H22B 109.5
C18 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C7 N1 S3 119.7(2)
C7 N1 H1 120.1
S3 N1 H1 120.1
C10 N2 C8 113.0(3)
C10 S1 C9 88.61(18)
C10 S2 C14 101.2(2)
O2 S3 O3 121.1(2)
O2 S3 N1 106.63(16)
O3 S3 N1 105.04(17)
O2 S3 C21 108.4(2)
O3 S3 C21 108.23(19)
N1 S3 C21 106.50(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.914(4)
C1 C2 1.379(5)
C1 C6 1.384(5)
C2 C3 1.384(5)
C2 H2 0.9300
C3 C4 1.368(5)
C3 H3 0.9300
C4 C5 1.373(5)
C4 H4 0.9300
C5 C6 1.396(5)
C5 H5 0.9300
C6 C7 1.522(5)
C7 N1 1.474(4)
C7 C8 1.571(5)
C7 H7 0.9800
C8 N2 1.454(4)
C8 C9 1.536(5)
C8 C11 1.553(5)
C9 O1 1.199(4)
C9 S1 1.774(4)
C10 N2 1.259(4)
C10 S2 1.743(4)
C10 S1 1.770(4)
C11 C12 1.511(5)
C11 C13 1.543(5)
C11 H11 0.9800
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.475(7)
C14 S2 1.805(5)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 C17 1.381(6)
C16 C21 1.391(5)
C16 H16 0.9300
C17 C18 1.372(6)
C17 H17 0.9300
C18 C19 1.379(5)
C18 C22 1.516(7)
C19 C20 1.364(5)
C19 H19 0.9300
C20 C21 1.376(5)
C20 H20 0.9300
C21 S3 1.746(4)
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
N1 S3 1.637(3)
N1 H1 0.8600
O2 S3 1.429(3)
O3 S3 1.429(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.1(5)
Br1 C1 C2 C3 -175.7(3)
C1 C2 C3 C4 -0.8(6)
C2 C3 C4 C5 0.1(6)
C3 C4 C5 C6 0.4(6)
C2 C1 C6 C5 -0.6(5)
Br1 C1 C6 C5 176.0(2)
C2 C1 C6 C7 -179.8(3)
Br1 C1 C6 C7 -3.2(4)
C4 C5 C6 C1 -0.1(5)
C4 C5 C6 C7 179.1(3)
C1 C6 C7 N1 137.5(3)
C5 C6 C7 N1 -41.6(4)
C1 C6 C7 C8 -97.6(4)
C5 C6 C7 C8 83.2(4)
N1 C7 C8 N2 -173.5(3)
C6 C7 C8 N2 59.0(3)
N1 C7 C8 C9 68.3(3)
C6 C7 C8 C9 -59.2(4)
N1 C7 C8 C11 -53.2(3)
C6 C7 C8 C11 179.3(3)
N2 C8 C9 O1 176.8(3)
C11 C8 C9 O1 56.8(4)
C7 C8 C9 O1 -66.8(4)
N2 C8 C9 S1 -1.3(3)
C11 C8 C9 S1 -121.3(3)
C7 C8 C9 S1 115.1(3)
N2 C8 C11 C12 68.1(4)
C9 C8 C11 C12 -172.0(3)
C7 C8 C11 C12 -50.6(4)
N2 C8 C11 C13 -58.3(4)
C9 C8 C11 C13 61.6(4)
C7 C8 C11 C13 -177.0(3)
C21 C16 C17 C18 -0.1(6)
C16 C17 C18 C19 1.5(7)
C16 C17 C18 C22 -176.3(4)
C17 C18 C19 C20 -1.4(6)
C22 C18 C19 C20 176.4(4)
C18 C19 C20 C21 -0.1(6)
C19 C20 C21 C16 1.5(6)
C19 C20 C21 S3 -171.0(3)
C17 C16 C21 C20 -1.4(6)
C17 C16 C21 S3 171.0(3)
C6 C7 N1 S3 -76.4(3)
C8 C7 N1 S3 157.0(2)
S2 C10 N2 C8 -179.0(3)
S1 C10 N2 C8 0.6(4)
C9 C8 N2 C10 0.5(4)
C11 C8 N2 C10 120.3(3)
C7 C8 N2 C10 -117.4(3)
N2 C10 S1 C9 -1.2(3)
S2 C10 S1 C9 178.5(2)
O1 C9 S1 C10 -176.8(3)
C8 C9 S1 C10 1.3(3)
N2 C10 S2 C14 8.9(4)
S1 C10 S2 C14 -170.7(2)
C15 C14 S2 C10 73.2(4)
C7 N1 S3 O2 -38.8(3)
C7 N1 S3 O3 -168.5(3)
C7 N1 S3 C21 76.8(3)
C20 C21 S3 O2 -172.1(3)
C16 C21 S3 O2 15.5(4)
C20 C21 S3 O3 -39.0(4)
C16 C21 S3 O3 148.6(3)
C20 C21 S3 N1 73.5(3)
C16 C21 S3 N1 -98.9(3)
|
1502052.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502052.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502052
loop_
_publ_author_name
'Jung, Hyo Sung'
'Ko, Kyoung Chul'
'Kim, Gun-Hee'
'Lee, Ah-Rah'
'Na, Yun-Cheol'
'Kang, Chulhun'
'Lee, Jin Yong'
'Kim, Jong Seung'
_publ_section_title
;
Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its
biological application.
;
_journal_issue 6
_journal_name_full 'Organic letters'
_journal_page_first 1498
_journal_page_last 1501
_journal_paper_doi 10.1021/ol2001864
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C23 H25 N O6'
_chemical_formula_weight 411.40
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 101.350(6)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 17.248(5)
_cell_length_b 8.517(3)
_cell_length_c 13.924(4)
_cell_measurement_reflns_used 1081
_cell_measurement_temperature 170(2)
_cell_measurement_theta_max 24.67
_cell_measurement_theta_min 2.41
_cell_volume 2005.5(11)
_computing_cell_refinement 'Bruker SMART'
_computing_data_collection 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.1206
_diffrn_reflns_av_sigmaI/netI 0.1717
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 10522
_diffrn_reflns_theta_full 26.00
_diffrn_reflns_theta_max 26.00
_diffrn_reflns_theta_min 2.41
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_type none
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.346
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 852
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.10
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.729
_refine_diff_density_min -0.260
_refine_diff_density_rms 0.069
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.876
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 271
_refine_ls_number_reflns 3938
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 0.877
_refine_ls_R_factor_all 0.1554
_refine_ls_R_factor_gt 0.0670
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1658
_refine_ls_wR_factor_ref 0.1899
_reflns_number_gt 1529
_reflns_number_total 3938
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol2001864_si_002.cif
_cod_data_source_block ym368p21c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 2005.6(11)
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502052
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3863(3) 0.6607(5) 0.0774(3) 0.0335(10) Uani 1 1 d . . .
C2 C 0.3301(2) 0.5332(5) 0.0469(3) 0.0310(10) Uani 1 1 d . . .
C3 C 0.3585(2) 0.3802(5) 0.0552(3) 0.0324(10) Uani 1 1 d . . .
H3 H 0.3229 0.2958 0.0356 0.039 Uiso 1 1 calc R . .
C4 C 0.4387(2) 0.3472(4) 0.0918(3) 0.0283(10) Uani 1 1 d . . .
C5 C 0.4707(2) 0.1938(4) 0.1014(3) 0.0300(10) Uani 1 1 d . . .
H5 H 0.4370 0.1067 0.0809 0.036 Uiso 1 1 calc R . .
C6 C 0.5482(2) 0.1685(4) 0.1391(3) 0.0293(10) Uani 1 1 d . . .
C7 C 0.5823(2) 0.0047(4) 0.1522(3) 0.0324(10) Uani 1 1 d . . .
H7A H 0.5825 -0.0324 0.2196 0.039 Uiso 1 1 calc R . .
H7B H 0.5491 -0.0679 0.1059 0.039 Uiso 1 1 calc R . .
C8 C 0.6654(2) 0.0053(4) 0.1336(3) 0.0365(11) Uani 1 1 d . . .
H8A H 0.6645 0.0348 0.0646 0.044 Uiso 1 1 calc R . .
H8B H 0.6882 -0.1014 0.1443 0.044 Uiso 1 1 calc R . .
C9 C 0.7172(2) 0.1212(5) 0.2015(3) 0.0400(11) Uani 1 1 d . . .
H9A H 0.7294 0.0775 0.2687 0.048 Uiso 1 1 calc R . .
H9B H 0.7678 0.1361 0.1792 0.048 Uiso 1 1 calc R . .
C10 C 0.7327(2) 0.3968(5) 0.2482(3) 0.0376(11) Uani 1 1 d . . .
H10A H 0.7667 0.4283 0.2019 0.045 Uiso 1 1 calc R . .
H10B H 0.7673 0.3540 0.3077 0.045 Uiso 1 1 calc R . .
C11 C 0.6895(2) 0.5401(5) 0.2758(3) 0.0360(11) Uani 1 1 d . . .
H11A H 0.7273 0.6279 0.2924 0.043 Uiso 1 1 calc R . .
H11B H 0.6672 0.5160 0.3344 0.043 Uiso 1 1 calc R . .
C12 C 0.6232(2) 0.5895(4) 0.1924(3) 0.0334(10) Uani 1 1 d . . .
H12A H 0.5925 0.6757 0.2147 0.040 Uiso 1 1 calc R . .
H12B H 0.6461 0.6290 0.1371 0.040 Uiso 1 1 calc R . .
C13 C 0.5690(2) 0.4529(4) 0.1581(3) 0.0281(9) Uani 1 1 d . . .
C14 C 0.6002(2) 0.2991(4) 0.1674(3) 0.0264(9) Uani 1 1 d . . .
C15 C 0.4914(2) 0.4715(4) 0.1207(3) 0.0278(9) Uani 1 1 d . . .
C16 C 0.2497(2) 0.5826(5) 0.0092(3) 0.0378(11) Uani 1 1 d . . .
H16 H 0.2414 0.6926 0.0125 0.045 Uiso 1 1 calc R . .
C17 C 0.1837(2) 0.4996(5) -0.0301(3) 0.0366(11) Uani 1 1 d . . .
C18 C 0.1110(3) 0.5869(7) -0.0660(3) 0.0538(13) Uani 1 1 d . A .
C19 C -0.0286(7) 0.5567(16) -0.1296(14) 0.076(4) Uiso 0.52(3) 1 d PD A 1
C20 C -0.0790(6) 0.4454(14) -0.1953(10) 0.050(4) Uiso 0.52(3) 1 d PD A 1
C19* C -0.0150(5) 0.5843(10) -0.1624(9) 0.037(4) Uiso 0.48(3) 1 d PD A 2
C20* C -0.0712(8) 0.490(2) -0.2335(17) 0.102(6) Uiso 0.48(3) 1 d PD A 2
C21 C 0.1795(2) 0.3231(5) -0.0462(4) 0.0422(11) Uani 1 1 d . . .
C22 C 0.1413(3) 0.0835(5) 0.0154(4) 0.0551(13) Uani 1 1 d . . .
H22A H 0.1924 0.0268 0.0260 0.066 Uiso 1 1 calc R . .
H22B H 0.1115 0.0589 -0.0512 0.066 Uiso 1 1 calc R . .
C23 C 0.0950(3) 0.0369(6) 0.0906(4) 0.0620(14) Uani 1 1 d . . .
H23A H 0.1238 0.0678 0.1557 0.093 Uiso 1 1 calc R . .
H23B H 0.0872 -0.0771 0.0886 0.093 Uiso 1 1 calc R . .
H23C H 0.0434 0.0895 0.0769 0.093 Uiso 1 1 calc R . .
N1 N 0.6774(2) 0.2740(4) 0.2030(2) 0.0339(8) Uani 1 1 d . . .
O1 O 0.36908(17) 0.8003(3) 0.07421(19) 0.0441(8) Uani 1 1 d . . .
O2 O 0.46357(16) 0.6238(3) 0.11257(17) 0.0318(7) Uani 1 1 d . . .
O3 O 0.1028(2) 0.7284(4) -0.0604(3) 0.0755(12) Uani 1 1 d . . .
O4 O 0.05319(17) 0.4921(4) -0.1097(2) 0.0604(10) Uani 1 1 d D . .
O5 O 0.19639(18) 0.2597(4) -0.1162(2) 0.0560(9) Uani 1 1 d . . .
O6 O 0.15445(17) 0.2520(3) 0.0267(2) 0.0457(8) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.055(3) 0.028(3) 0.022(2) -0.0017(19) 0.018(2) 0.001(2)
C2 0.040(3) 0.030(2) 0.025(2) 0.0014(18) 0.0115(18) 0.006(2)
C3 0.048(3) 0.025(3) 0.028(2) -0.0021(18) 0.016(2) -0.0013(19)
C4 0.035(3) 0.023(2) 0.029(2) -0.0002(18) 0.0109(19) -0.0002(19)
C5 0.038(3) 0.026(2) 0.028(2) -0.0007(18) 0.0100(19) -0.0017(19)
C6 0.045(3) 0.018(2) 0.027(2) 0.0002(18) 0.0130(19) 0.0035(19)
C7 0.042(3) 0.019(2) 0.037(2) -0.0020(18) 0.0101(19) -0.0001(19)
C8 0.046(3) 0.022(2) 0.043(3) 0.0027(19) 0.013(2) 0.0048(19)
C9 0.047(3) 0.032(3) 0.042(3) 0.002(2) 0.012(2) 0.003(2)
C10 0.042(3) 0.037(3) 0.035(3) -0.002(2) 0.008(2) -0.004(2)
C11 0.042(3) 0.029(2) 0.039(3) -0.0059(19) 0.013(2) -0.008(2)
C12 0.046(3) 0.022(2) 0.034(2) 0.0011(19) 0.013(2) -0.0065(19)
C13 0.039(3) 0.019(2) 0.028(2) 0.0015(17) 0.0099(19) -0.0021(18)
C14 0.033(3) 0.027(2) 0.021(2) -0.0006(17) 0.0101(18) -0.0010(19)
C15 0.038(3) 0.019(2) 0.030(2) 0.0003(17) 0.0147(19) 0.0009(19)
C16 0.043(3) 0.034(3) 0.037(3) 0.000(2) 0.010(2) 0.009(2)
C17 0.044(3) 0.032(3) 0.034(3) 0.001(2) 0.010(2) 0.012(2)
C18 0.047(3) 0.065(4) 0.046(3) -0.009(3) 0.000(2) 0.011(3)
C21 0.028(3) 0.047(3) 0.049(3) -0.003(3) 0.001(2) 0.003(2)
C22 0.060(3) 0.036(3) 0.068(3) -0.001(3) 0.009(3) 0.002(2)
C23 0.052(3) 0.042(3) 0.087(4) 0.007(3) 0.001(3) 0.006(2)
N1 0.038(2) 0.028(2) 0.036(2) -0.0032(16) 0.0091(16) -0.0003(17)
O1 0.065(2) 0.0211(18) 0.0473(19) -0.0005(13) 0.0131(15) 0.0066(14)
O2 0.0418(19) 0.0181(16) 0.0354(17) -0.0006(12) 0.0068(13) 0.0024(13)
O3 0.070(3) 0.046(2) 0.103(3) -0.007(2) -0.001(2) 0.0273(19)
O4 0.0376(19) 0.066(2) 0.071(2) -0.0182(18) -0.0060(16) 0.0215(17)
O5 0.055(2) 0.053(2) 0.064(2) -0.0192(18) 0.0231(17) 0.0053(16)
O6 0.050(2) 0.0337(19) 0.053(2) -0.0030(15) 0.0074(15) 0.0025(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 116.7(4)
O1 C1 C2 124.7(4)
O2 C1 C2 118.6(3)
C3 C2 C16 127.0(4)
C3 C2 C1 118.0(4)
C16 C2 C1 115.1(4)
C2 C3 C4 121.6(4)
C2 C3 H3 119.2
C4 C3 H3 119.2
C15 C4 C3 119.3(3)
C15 C4 C5 116.9(4)
C3 C4 C5 123.8(4)
C6 C5 C4 121.3(4)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C14 120.0(4)
C5 C6 C7 121.6(3)
C14 C6 C7 118.4(3)
C8 C7 C6 109.7(3)
C8 C7 H7A 109.7
C6 C7 H7A 109.7
C8 C7 H7B 109.7
C6 C7 H7B 109.7
H7A C7 H7B 108.2
C7 C8 C9 110.9(3)
C7 C8 H8A 109.5
C9 C8 H8A 109.5
C7 C8 H8B 109.5
C9 C8 H8B 109.5
H8A C8 H8B 108.1
N1 C9 C8 111.2(3)
N1 C9 H9A 109.4
C8 C9 H9A 109.4
N1 C9 H9B 109.4
C8 C9 H9B 109.4
H9A C9 H9B 108.0
N1 C10 C11 111.7(3)
N1 C10 H10A 109.3
C11 C10 H10A 109.3
N1 C10 H10B 109.3
C11 C10 H10B 109.3
H10A C10 H10B 107.9
C10 C11 C12 111.2(3)
C10 C11 H11A 109.4
C12 C11 H11A 109.4
C10 C11 H11B 109.4
C12 C11 H11B 109.4
H11A C11 H11B 108.0
C13 C12 C11 110.7(3)
C13 C12 H12A 109.5
C11 C12 H12A 109.5
C13 C12 H12B 109.5
C11 C12 H12B 109.5
H12A C12 H12B 108.1
C15 C13 C14 118.5(3)
C15 C13 C12 122.6(3)
C14 C13 C12 118.9(3)
N1 C14 C13 120.9(3)
N1 C14 C6 119.9(3)
C13 C14 C6 119.1(3)
C13 C15 O2 116.5(3)
C13 C15 C4 124.1(3)
O2 C15 C4 119.4(3)
C17 C16 C2 131.4(4)
C17 C16 H16 114.3
C2 C16 H16 114.3
C16 C17 C18 117.9(4)
C16 C17 C21 125.9(4)
C18 C17 C21 116.1(4)
O3 C18 O4 122.9(4)
O3 C18 C17 125.8(5)
O4 C18 C17 111.3(4)
C20 C19 O4 107.4(8)
C20* C19* O4 113.4(9)
O5 C21 O6 125.8(4)
O5 C21 C17 123.6(4)
O6 C21 C17 110.6(4)
O6 C22 C23 106.2(4)
O6 C22 H22A 110.5
C23 C22 H22A 110.5
O6 C22 H22B 110.5
C23 C22 H22B 110.5
H22A C22 H22B 108.7
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C14 N1 C10 123.8(3)
C14 N1 C9 124.5(3)
C10 N1 C9 111.7(3)
C1 O2 C15 123.1(3)
C18 O4 C19* 110.7(5)
C18 O4 C19 117.2(5)
C19* O4 C19 23.3(6)
C21 O6 C22 115.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.224(4)
C1 O2 1.363(5)
C1 C2 1.462(5)
C2 C3 1.390(5)
C2 C16 1.445(5)
C3 C4 1.405(5)
C3 H3 0.9500
C4 C15 1.402(5)
C4 C5 1.414(5)
C5 C6 1.355(5)
C5 H5 0.9500
C6 C14 1.435(5)
C6 C7 1.511(5)
C7 C8 1.507(5)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.528(5)
C8 H8A 0.9900
C8 H8B 0.9900
C9 N1 1.474(5)
C9 H9A 0.9900
C9 H9B 0.9900
C10 N1 1.471(5)
C10 C11 1.518(5)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.519(5)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.510(5)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C15 1.346(5)
C13 C14 1.413(5)
C14 N1 1.343(5)
C15 O2 1.380(4)
C16 C17 1.359(5)
C16 H16 0.9500
C17 C18 1.460(6)
C17 C21 1.520(6)
C18 O3 1.218(6)
C18 O4 1.333(6)
C19 C20 1.476(2)
C19 O4 1.488(11)
C19* C20* 1.477(2)
C19* O4 1.483(2)
C21 O5 1.199(5)
C21 O6 1.325(5)
C22 O6 1.457(5)
C22 C23 1.490(6)
C22 H22A 0.9900
C22 H22B 0.9900
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -179.9(3)
O2 C1 C2 C3 -0.1(5)
O1 C1 C2 C16 1.2(5)
O2 C1 C2 C16 -179.1(3)
C16 C2 C3 C4 179.0(4)
C1 C2 C3 C4 0.1(5)
C2 C3 C4 C15 0.0(6)
C2 C3 C4 C5 -179.8(3)
C15 C4 C5 C6 1.7(5)
C3 C4 C5 C6 -178.6(4)
C4 C5 C6 C14 -2.0(5)
C4 C5 C6 C7 178.3(3)
C5 C6 C7 C8 145.0(4)
C14 C6 C7 C8 -34.7(5)
C6 C7 C8 C9 57.3(4)
C7 C8 C9 N1 -47.4(4)
N1 C10 C11 C12 -46.9(4)
C10 C11 C12 C13 53.2(4)
C11 C12 C13 C15 149.4(4)
C11 C12 C13 C14 -29.3(5)
C15 C13 C14 N1 179.0(4)
C12 C13 C14 N1 -2.3(5)
C15 C13 C14 C6 -1.5(5)
C12 C13 C14 C6 177.2(3)
C5 C6 C14 N1 -178.6(3)
C7 C6 C14 N1 1.1(5)
C5 C6 C14 C13 1.9(5)
C7 C6 C14 C13 -178.3(3)
C14 C13 C15 O2 -179.7(3)
C12 C13 C15 O2 1.6(5)
C14 C13 C15 C4 1.3(6)
C12 C13 C15 C4 -177.4(3)
C3 C4 C15 C13 178.9(4)
C5 C4 C15 C13 -1.3(5)
C3 C4 C15 O2 -0.1(5)
C5 C4 C15 O2 179.7(3)
C3 C2 C16 C17 -2.9(7)
C1 C2 C16 C17 176.0(4)
C2 C16 C17 C18 -177.2(4)
C2 C16 C17 C21 -1.3(7)
C16 C17 C18 O3 -3.2(7)
C21 C17 C18 O3 -179.5(5)
C16 C17 C18 O4 174.8(4)
C21 C17 C18 O4 -1.6(6)
C16 C17 C21 O5 -83.2(6)
C18 C17 C21 O5 92.8(5)
C16 C17 C21 O6 97.3(5)
C18 C17 C21 O6 -86.7(4)
C13 C14 N1 C10 9.5(5)
C6 C14 N1 C10 -169.9(3)
C13 C14 N1 C9 -170.4(3)
C6 C14 N1 C9 10.1(5)
C11 C10 N1 C14 16.0(5)
C11 C10 N1 C9 -164.0(3)
C8 C9 N1 C14 13.7(5)
C8 C9 N1 C10 -166.3(3)
O1 C1 O2 C15 179.8(3)
C2 C1 O2 C15 0.0(5)
C13 C15 O2 C1 -179.0(3)
C4 C15 O2 C1 0.1(5)
O3 C18 O4 C19* 9.0(9)
C17 C18 O4 C19* -169.0(7)
O3 C18 O4 C19 -15.5(12)
C17 C18 O4 C19 166.4(10)
C20* C19* O4 C18 164.3(10)
C20* C19* O4 C19 -84.9(16)
C20 C19 O4 C18 168.5(7)
C20 C19 O4 C19* 89.2(16)
O5 C21 O6 C22 -4.7(6)
C17 C21 O6 C22 174.9(3)
C23 C22 O6 C21 -165.9(4)
|
1502053.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502053.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502053
loop_
_publ_author_name
'Kurono, Nobuhito'
'Yoshikawa, Tatsuya'
'Yamasaki, Mikio'
'Ohkuma, Takeshi'
_publ_section_title
;
Enantioselective hydrocyanation of aldehydes catalyzed by
[Li{Ru(phgly)2(binap)}]X (X = Cl, Br).
;
_journal_issue 5
_journal_name_full 'Organic letters'
_journal_page_first 1254
_journal_page_last 1257
_journal_paper_doi 10.1021/ol200187d
_journal_volume 13
_journal_year 2011
_chemical_absolute_configuration ad
_chemical_formula_moiety
'(C60 H48 N2 O4 P2 Ru), 2.5(C4 H8 O), Li, 2H2O'
_chemical_formula_sum 'C70 H72 Br Li N2 O8.5 P2 Ru'
_chemical_formula_weight 1327.21
_space_group_IT_number 19
_symmetry_cell_setting orthorhombic
_symmetry_Int_Tables_number 19
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_cell_angle_alpha 90.0000
_cell_angle_beta 90.0000
_cell_angle_gamma 90.0000
_cell_formula_units_Z 4
_cell_length_a 16.1277(6)
_cell_length_b 18.8951(6)
_cell_length_c 20.9790(15)
_cell_measurement_reflns_used 34479
_cell_measurement_temperature 123.1
_cell_measurement_theta_max 25.3
_cell_measurement_theta_min 3.1
_cell_volume 6393.0(6)
_computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics 'ORTEP (Johnson, 1976)'
_computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution SIR97
_diffrn_ambient_temperature 123.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method \w
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71075
_diffrn_reflns_av_R_equivalents 0.058
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 38552
_diffrn_reflns_theta_full 25.00
_diffrn_reflns_theta_max 25.34
_exptl_absorpt_coefficient_mu 0.980
_exptl_absorpt_correction_T_max 0.783
_exptl_absorpt_correction_T_min 0.548
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour brown
_exptl_crystal_density_diffrn 1.379
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description chunk
_exptl_crystal_F_000 2744.00
_exptl_crystal_size_max 0.80
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.25
_refine_diff_density_max 1.29
_refine_diff_density_min -0.69
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 5159 Friedel Pairs'
_refine_ls_abs_structure_Flack 0.007(9)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.003
_refine_ls_hydrogen_treatment constr
_refine_ls_number_parameters 794
_refine_ls_number_reflns 11483
_refine_ls_number_restraints 66
_refine_ls_R_factor_gt 0.0465
_refine_ls_shift/su_max 0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_ref 0.1113
_reflns_number_gt 9403
_reflns_number_total 11483
_reflns_threshold_expression F^2^>2.0\s(F^2^)
_cod_data_source_file ol200187d_si_002.cif
_cod_data_source_block '_kurono081119'
_cod_original_cell_volume 6393.0(5)
_cod_original_formula_sum 'C70 H72 Br Li N2 O8.50 P2 Ru '
_cod_database_code 1502053
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ru(1) Ru 0.33153(2) 0.541288(19) 0.408114(17) 0.02099(10) Uani 1.00 1 d .
Br(1) Br 0.07366(4) 0.52775(3) 0.49527(3) 0.03887(14) Uani 1.00 1 d .
P(1) P 0.44625(8) 0.61199(6) 0.41295(6) 0.0212(2) Uani 1.00 1 d .
P(2) P 0.41257(8) 0.45266(6) 0.36993(5) 0.0215(2) Uani 1.00 1 d .
O(1) O 0.3344(2) 0.50123(15) 0.50149(15) 0.0257(6) Uani 1.00 1 d .
O(2) O 0.3054(2) 0.52539(18) 0.60335(14) 0.0330(8) Uani 1.00 1 d .
O(3) O 0.2902(2) 0.58398(17) 0.32061(15) 0.0261(7) Uani 1.00 1 d .
O(4) O 0.2099(2) 0.56710(17) 0.23575(16) 0.0345(8) Uani 1.00 1 d .
O(5) O 0.0950(3) 0.3020(2) 0.5284(2) 0.0600(12) Uani 1.00 1 d D
O(6) O 0.3279(4) 0.2305(2) 0.6667(2) 0.0804(15) Uani 1.00 1 d .
O(7) O 0.5413(5) 0.3414(4) 0.6514(4) 0.061(2) Uani 0.50 1 d PDU
O(8) O 0.1903(2) 0.4079(2) 0.5875(2) 0.0563(11) Uani 1.00 1 d .
O(9) O 0.3749(3) 0.3612(2) 0.6143(2) 0.0647(13) Uani 1.00 1 d .
N(1) N 0.2571(2) 0.6169(2) 0.46300(18) 0.0255(9) Uani 1.00 1 d .
N(2) N 0.2192(2) 0.4814(2) 0.38791(17) 0.0241(9) Uani 1.00 1 d .
C(1) C 0.4164(3) 0.7071(2) 0.4140(2) 0.0241(10) Uani 1.00 1 d .
C(2) C 0.4500(3) 0.7559(2) 0.4570(2) 0.0282(11) Uani 1.00 1 d .
C(3) C 0.4170(3) 0.8240(2) 0.4599(2) 0.0310(12) Uani 1.00 1 d .
C(4) C 0.3510(3) 0.8437(2) 0.4210(2) 0.0296(12) Uani 1.00 1 d .
C(5) C 0.3198(3) 0.7960(2) 0.3779(2) 0.0298(11) Uani 1.00 1 d .
C(6) C 0.3502(3) 0.7277(2) 0.3741(2) 0.0259(11) Uani 1.00 1 d .
C(7) C 0.5234(3) 0.6088(2) 0.4774(2) 0.0216(10) Uani 1.00 1 d .
C(8) C 0.5943(3) 0.6504(2) 0.4733(2) 0.0269(11) Uani 1.00 1 d .
C(9) C 0.6522(3) 0.6504(2) 0.5218(2) 0.0313(12) Uani 1.00 1 d .
C(10) C 0.6399(3) 0.6072(2) 0.5749(2) 0.0357(13) Uani 1.00 1 d .
C(11) C 0.5712(3) 0.5643(2) 0.5782(2) 0.0313(11) Uani 1.00 1 d .
C(12) C 0.5122(3) 0.5643(2) 0.5303(2) 0.0295(11) Uani 1.00 1 d .
C(13) C 0.5139(3) 0.6028(2) 0.3426(2) 0.0217(10) Uani 1.00 1 d .
C(14) C 0.5053(3) 0.6510(2) 0.2904(2) 0.0239(11) Uani 1.00 1 d .
C(15) C 0.5528(3) 0.6432(2) 0.2370(2) 0.0257(11) Uani 1.00 1 d .
C(16) C 0.6088(3) 0.5865(2) 0.2301(2) 0.0259(11) Uani 1.00 1 d .
C(17) C 0.6588(3) 0.5775(2) 0.1749(2) 0.0316(12) Uani 1.00 1 d .
C(18) C 0.7139(3) 0.5231(2) 0.1700(2) 0.0322(12) Uani 1.00 1 d .
C(19) C 0.7214(3) 0.4744(2) 0.2190(2) 0.0351(12) Uani 1.00 1 d .
C(20) C 0.6744(3) 0.4799(2) 0.2732(2) 0.0252(10) Uani 1.00 1 d .
C(21) C 0.6171(3) 0.5367(2) 0.2809(2) 0.0239(10) Uani 1.00 1 d .
C(22) C 0.5675(2) 0.5452(2) 0.33742(19) 0.0205(9) Uani 1.00 1 d .
C(23) C 0.5789(3) 0.4930(2) 0.3913(2) 0.0217(10) Uani 1.00 1 d .
C(24) C 0.6576(3) 0.4907(2) 0.4227(2) 0.0249(10) Uani 1.00 1 d .
C(25) C 0.7235(2) 0.5369(2) 0.4087(2) 0.0279(10) Uani 1.00 1 d .
C(26) C 0.7983(3) 0.5323(2) 0.4381(2) 0.0297(11) Uani 1.00 1 d .
C(27) C 0.8123(3) 0.4809(2) 0.4846(2) 0.0400(14) Uani 1.00 1 d .
C(28) C 0.7492(3) 0.4360(2) 0.5022(2) 0.0399(13) Uani 1.00 1 d .
C(29) C 0.6704(3) 0.4402(2) 0.4724(2) 0.0321(11) Uani 1.00 1 d .
C(30) C 0.6034(3) 0.3951(2) 0.4903(2) 0.0369(13) Uani 1.00 1 d .
C(31) C 0.5300(3) 0.3989(2) 0.4597(2) 0.0319(12) Uani 1.00 1 d .
C(32) C 0.5155(3) 0.4476(2) 0.4080(2) 0.0271(10) Uani 1.00 1 d .
C(33) C 0.3605(3) 0.3668(2) 0.3845(2) 0.0233(11) Uani 1.00 1 d .
C(34) C 0.3348(3) 0.3235(2) 0.3340(2) 0.0280(10) Uani 1.00 1 d .
C(35) C 0.2845(3) 0.2658(2) 0.3451(2) 0.0363(13) Uani 1.00 1 d .
C(36) C 0.2589(3) 0.2498(2) 0.4061(2) 0.0374(13) Uani 1.00 1 d .
C(37) C 0.2834(4) 0.2910(2) 0.4563(2) 0.0430(15) Uani 1.00 1 d .
C(38) C 0.3322(3) 0.3506(2) 0.4457(2) 0.0324(11) Uani 1.00 1 d .
C(39) C 0.4437(2) 0.4440(2) 0.2866(2) 0.0207(10) Uani 1.00 1 d .
C(40) C 0.4190(3) 0.4931(2) 0.2411(2) 0.0235(10) Uani 1.00 1 d .
C(41) C 0.4435(3) 0.4858(2) 0.1774(2) 0.0276(11) Uani 1.00 1 d .
C(42) C 0.4951(3) 0.4319(2) 0.1600(2) 0.0275(11) Uani 1.00 1 d .
C(43) C 0.5212(3) 0.3823(2) 0.2056(2) 0.0254(11) Uani 1.00 1 d .
C(44) C 0.4956(3) 0.3888(2) 0.2675(2) 0.0243(10) Uani 1.00 1 d .
C(45) C 0.2988(3) 0.6203(2) 0.5261(2) 0.0255(11) Uani 1.00 1 d .
C(46) C 0.2629(3) 0.6698(2) 0.5752(2) 0.0259(11) Uani 1.00 1 d .
C(47) C 0.3115(3) 0.7271(2) 0.5954(2) 0.0374(13) Uani 1.00 1 d .
C(48) C 0.2823(4) 0.7745(3) 0.6402(2) 0.0408(14) Uani 1.00 1 d .
C(49) C 0.2051(3) 0.7653(2) 0.6658(2) 0.0339(12) Uani 1.00 1 d .
C(50) C 0.1558(3) 0.7091(2) 0.6456(2) 0.0354(13) Uani 1.00 1 d .
C(51) C 0.1849(3) 0.6617(2) 0.6012(2) 0.0314(12) Uani 1.00 1 d .
C(52) C 0.3120(2) 0.5436(2) 0.5473(2) 0.0260(10) Uani 1.00 1 d .
C(53) C 0.2091(3) 0.4778(2) 0.3174(2) 0.0269(11) Uani 1.00 1 d .
C(54) C 0.1272(3) 0.4487(2) 0.2945(2) 0.0331(12) Uani 1.00 1 d .
C(55) C 0.0541(3) 0.4587(4) 0.3264(2) 0.0528(16) Uani 1.00 1 d .
C(56) C -0.0212(4) 0.4326(4) 0.3033(3) 0.065(2) Uani 1.00 1 d .
C(57) C -0.0207(4) 0.3941(3) 0.2468(3) 0.0505(16) Uani 1.00 1 d .
C(58) C 0.0513(4) 0.3857(3) 0.2138(2) 0.0438(15) Uani 1.00 1 d .
C(59) C 0.1250(3) 0.4115(2) 0.2369(2) 0.0339(12) Uani 1.00 1 d .
C(60) C 0.2354(3) 0.5479(2) 0.2887(2) 0.0275(10) Uani 1.00 1 d .
C(61) C 0.0673(4) 0.3213(4) 0.4648(3) 0.0633(19) Uani 1.00 1 d D
C(62) C -0.0242(5) 0.3254(5) 0.4677(4) 0.087(2) Uani 1.00 1 d D
C(63) C -0.0425(5) 0.3428(4) 0.5376(4) 0.083(2) Uani 1.00 1 d D
C(64) C 0.0237(4) 0.3014(3) 0.5688(3) 0.069(2) Uani 1.00 1 d D
C(65) C 0.2792(4) 0.1790(4) 0.6328(4) 0.069(2) Uani 1.00 1 d .
C(66) C 0.1911(5) 0.2025(3) 0.6383(3) 0.067(2) Uani 1.00 1 d .
C(67) C 0.1926(5) 0.2432(4) 0.7022(4) 0.082(2) Uani 1.00 1 d .
C(68) C 0.2810(5) 0.2487(4) 0.7210(3) 0.073(2) Uani 1.00 1 d .
C(69) C 0.5607(13) 0.4001(6) 0.6892(7) 0.101(4) Uani 0.50 1 d PDU
C(70) C 0.5785(15) 0.3793(7) 0.7523(7) 0.112(5) Uani 0.50 1 d PDU
C(71) C 0.5265(9) 0.3077(5) 0.7579(5) 0.061(3) Uani 0.50 1 d PDU
C(72) C 0.5383(7) 0.2822(5) 0.6941(5) 0.043(2) Uani 0.50 1 d PDU
Li(1) Li 0.2948(7) 0.4339(4) 0.6421(4) 0.046(2) Uani 1.00 1 d .
H(1NA) H 0.2568 0.6606 0.4436 0.031 Uiso 1.00 1 c R
H(1NB) H 0.2034 0.6013 0.4672 0.031 Uiso 1.00 1 c R
H(2) H 0.4948 0.7429 0.4838 0.034 Uiso 1.00 1 c R
H(2NA) H 0.2235 0.4365 0.4046 0.029 Uiso 1.00 1 c R
H(2NB) H 0.1741 0.5032 0.4061 0.029 Uiso 1.00 1 c R
H(3) H 0.4398 0.8574 0.4888 0.037 Uiso 1.00 1 c R
H(4) H 0.3278 0.8897 0.4242 0.035 Uiso 1.00 1 c R
H(5) H 0.2764 0.8102 0.3501 0.036 Uiso 1.00 1 c R
H(6) H 0.3267 0.6949 0.3449 0.031 Uiso 1.00 1 c R
H(8) H 0.6030 0.6793 0.4368 0.032 Uiso 1.00 1 c R
H(9) H 0.7000 0.6795 0.5190 0.038 Uiso 1.00 1 c R
H(10) H 0.6790 0.6074 0.6088 0.043 Uiso 1.00 1 c R
H(11) H 0.5641 0.5341 0.6141 0.038 Uiso 1.00 1 c R
H(12) H 0.4648 0.5345 0.5332 0.035 Uiso 1.00 1 c R
H(14) H 0.4663 0.6885 0.2930 0.029 Uiso 1.00 1 c R
H(15) H 0.5480 0.6769 0.2036 0.031 Uiso 1.00 1 c R
H(17) H 0.6537 0.6101 0.1407 0.038 Uiso 1.00 1 c R
H(18) H 0.7472 0.5185 0.1329 0.039 Uiso 1.00 1 c R
H(19) H 0.7598 0.4366 0.2150 0.042 Uiso 1.00 1 c R
H(20) H 0.6801 0.4455 0.3059 0.030 Uiso 1.00 1 c R
H(25) H 0.7153 0.5727 0.3775 0.033 Uiso 1.00 1 c R
H(26) H 0.8414 0.5643 0.4270 0.036 Uiso 1.00 1 c R
H(27) H 0.8652 0.4769 0.5041 0.048 Uiso 1.00 1 c R
H(28) H 0.7584 0.4019 0.5347 0.048 Uiso 1.00 1 c R
H(30) H 0.6106 0.3621 0.5241 0.044 Uiso 1.00 1 c R
H(31) H 0.4863 0.3684 0.4727 0.038 Uiso 1.00 1 c R
H(34) H 0.3522 0.3339 0.2918 0.034 Uiso 1.00 1 c R
H(35) H 0.2673 0.2369 0.3105 0.044 Uiso 1.00 1 c R
H(36) H 0.2242 0.2100 0.4133 0.045 Uiso 1.00 1 c R
H(37) H 0.2670 0.2790 0.4985 0.052 Uiso 1.00 1 c R
H(38) H 0.3464 0.3806 0.4804 0.039 Uiso 1.00 1 c R
H(40) H 0.3851 0.5319 0.2533 0.028 Uiso 1.00 1 c R
H(41) H 0.4242 0.5184 0.1462 0.033 Uiso 1.00 1 c R
H(42) H 0.5135 0.4281 0.1171 0.033 Uiso 1.00 1 c R
H(43) H 0.5564 0.3443 0.1935 0.031 Uiso 1.00 1 c R
H(44) H 0.5134 0.3551 0.2981 0.029 Uiso 1.00 1 c R
H(45) H 0.3556 0.6391 0.5171 0.031 Uiso 1.00 1 c R
H(47) H 0.3654 0.7334 0.5780 0.045 Uiso 1.00 1 c R
H(48) H 0.3156 0.8134 0.6531 0.049 Uiso 1.00 1 c R
H(49) H 0.1851 0.7972 0.6973 0.041 Uiso 1.00 1 c R
H(50) H 0.1016 0.7034 0.6627 0.042 Uiso 1.00 1 c R
H(51) H 0.1511 0.6231 0.5884 0.038 Uiso 1.00 1 c R
H(53) H 0.2516 0.4429 0.3027 0.032 Uiso 1.00 1 c R
H(55) H 0.0545 0.4843 0.3654 0.063 Uiso 1.00 1 c R
H(56) H -0.0715 0.4408 0.3257 0.079 Uiso 1.00 1 c R
H(57) H -0.0705 0.3738 0.2312 0.061 Uiso 1.00 1 c R
H(58) H 0.0505 0.3615 0.1742 0.053 Uiso 1.00 1 c R
H(59) H 0.1748 0.4041 0.2136 0.041 Uiso 1.00 1 c R
H(61A) H 0.0849 0.2851 0.4334 0.076 Uiso 1.00 1 c R
H(61B) H 0.0910 0.3675 0.4521 0.076 Uiso 1.00 1 c R
H(62A) H -0.0496 0.2797 0.4553 0.105 Uiso 1.00 1 c R
H(62B) H -0.0454 0.3630 0.4392 0.105 Uiso 1.00 1 c R
H(63A) H -0.0372 0.3940 0.5464 0.100 Uiso 1.00 1 c R
H(63B) H -0.0984 0.3264 0.5505 0.100 Uiso 1.00 1 c R
H(64A) H 0.0375 0.3226 0.6107 0.083 Uiso 1.00 1 c R
H(64B) H 0.0049 0.2522 0.5759 0.083 Uiso 1.00 1 c R
H(65A) H 0.2864 0.1315 0.6518 0.083 Uiso 1.00 1 c R
H(65B) H 0.2962 0.1770 0.5875 0.083 Uiso 1.00 1 c R
H(66A) H 0.1528 0.1616 0.6401 0.081 Uiso 1.00 1 c R
H(66B) H 0.1752 0.2337 0.6025 0.081 Uiso 1.00 1 c R
H(67A) H 0.1681 0.2909 0.6968 0.099 Uiso 1.00 1 c R
H(67B) H 0.1607 0.2173 0.7350 0.099 Uiso 1.00 1 c R
H(68A) H 0.2941 0.2976 0.7348 0.088 Uiso 1.00 1 c R
H(68B) H 0.2932 0.2160 0.7566 0.088 Uiso 1.00 1 c R
H(69A) H 0.5134 0.4334 0.6892 0.122 Uiso 0.50 1 c PR
H(69B) H 0.6093 0.4248 0.6709 0.122 Uiso 0.50 1 c PR
H(70A) H 0.5594 0.4150 0.7835 0.134 Uiso 0.50 1 c PR
H(70B) H 0.6386 0.3707 0.7584 0.134 Uiso 0.50 1 c PR
H(71A) H 0.5501 0.2751 0.7901 0.073 Uiso 0.50 1 c PR
H(71B) H 0.4674 0.3168 0.7675 0.073 Uiso 0.50 1 c PR
H(72A) H 0.5906 0.2550 0.6914 0.051 Uiso 0.50 1 c PR
H(72B) H 0.4919 0.2505 0.6822 0.051 Uiso 0.50 1 c PR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ru(1) 0.0216(2) 0.02885(18) 0.01249(16) 0.00047(17) 0.00136(17) -0.00110(16)
Br(1) 0.0356(3) 0.0481(3) 0.0330(2) -0.0040(2) 0.0104(2) -0.0091(2)
P(1) 0.0230(6) 0.0271(5) 0.0135(5) 0.0008(4) 0.0007(5) -0.0006(4)
P(2) 0.0238(6) 0.0274(6) 0.0135(5) -0.0013(5) 0.0005(4) 0.0013(4)
O(1) 0.0299(19) 0.0305(15) 0.0168(15) 0.0017(15) 0.0025(17) -0.0009(13)
O(2) 0.039(2) 0.044(2) 0.0161(17) -0.0064(16) 0.0017(14) 0.0007(14)
O(3) 0.028(2) 0.0333(17) 0.0170(16) -0.0006(15) 0.0009(15) -0.0023(14)
O(4) 0.047(2) 0.0323(18) 0.0241(18) -0.0003(16) -0.0115(18) 0.0009(14)
O(5) 0.053(3) 0.065(2) 0.062(3) -0.002(2) -0.002(2) -0.005(2)
O(6) 0.085(4) 0.078(3) 0.078(3) -0.015(3) 0.007(3) -0.004(2)
O(7) 0.031(4) 0.072(5) 0.080(5) -0.023(4) -0.011(4) 0.047(4)
O(8) 0.048(2) 0.071(2) 0.050(2) -0.003(2) 0.005(2) 0.000(2)
O(9) 0.074(3) 0.065(2) 0.055(2) 0.014(2) 0.013(2) -0.003(2)
N(1) 0.026(2) 0.033(2) 0.017(2) -0.0002(19) 0.0007(17) 0.0033(16)
N(2) 0.025(2) 0.031(2) 0.0164(19) 0.0018(17) 0.0005(17) -0.0004(15)
C(1) 0.028(2) 0.027(2) 0.018(2) 0.0026(19) 0.007(2) 0.0000(19)
C(2) 0.032(3) 0.032(2) 0.021(2) -0.000(2) 0.006(2) 0.0008(19)
C(3) 0.037(3) 0.026(2) 0.030(2) -0.004(2) 0.008(2) -0.004(2)
C(4) 0.029(3) 0.029(2) 0.030(2) 0.002(2) 0.016(2) -0.004(2)
C(5) 0.022(3) 0.035(2) 0.032(2) 0.005(2) 0.010(2) 0.005(2)
C(6) 0.020(2) 0.039(2) 0.018(2) -0.002(2) 0.002(2) 0.000(2)
C(7) 0.023(2) 0.028(2) 0.014(2) 0.005(2) -0.003(2) 0.0006(18)
C(8) 0.028(3) 0.035(2) 0.018(2) -0.000(2) 0.003(2) -0.0038(19)
C(9) 0.026(3) 0.036(2) 0.031(2) -0.005(2) -0.003(2) -0.007(2)
C(10) 0.033(3) 0.055(3) 0.019(2) -0.000(2) -0.009(2) -0.001(2)
C(11) 0.028(3) 0.049(2) 0.017(2) -0.002(2) 0.000(2) 0.006(2)
C(12) 0.027(3) 0.042(2) 0.020(2) 0.002(2) 0.001(2) -0.000(2)
C(13) 0.022(2) 0.028(2) 0.015(2) -0.008(2) 0.000(2) 0.0029(18)
C(14) 0.027(3) 0.023(2) 0.022(2) -0.000(2) -0.003(2) 0.0011(18)
C(15) 0.036(3) 0.031(2) 0.010(2) 0.002(2) -0.000(2) 0.0018(18)
C(16) 0.028(3) 0.034(2) 0.016(2) -0.006(2) 0.003(2) 0.0007(19)
C(17) 0.035(3) 0.039(2) 0.020(2) -0.002(2) 0.006(2) 0.003(2)
C(18) 0.037(3) 0.037(2) 0.022(2) -0.002(2) 0.015(2) -0.005(2)
C(19) 0.032(3) 0.041(3) 0.032(2) 0.001(2) 0.003(2) -0.003(2)
C(20) 0.027(2) 0.028(2) 0.021(2) 0.000(2) 0.007(2) -0.0017(17)
C(21) 0.024(2) 0.024(2) 0.023(2) -0.005(2) -0.0045(19) -0.000(2)
C(22) 0.021(2) 0.025(2) 0.015(2) -0.005(2) -0.0023(18) 0.0003(18)
C(23) 0.021(2) 0.027(2) 0.017(2) 0.000(2) -0.000(2) 0.0006(17)
C(24) 0.032(3) 0.030(2) 0.013(2) 0.005(2) -0.003(2) 0.0001(17)
C(25) 0.025(2) 0.038(2) 0.020(2) 0.003(2) -0.002(2) -0.006(2)
C(26) 0.030(2) 0.034(2) 0.025(2) -0.001(2) 0.002(2) -0.004(2)
C(27) 0.035(3) 0.046(3) 0.039(3) 0.005(2) -0.011(2) -0.003(2)
C(28) 0.040(3) 0.043(2) 0.036(3) 0.003(2) -0.017(2) 0.008(2)
C(29) 0.035(3) 0.034(2) 0.027(2) 0.004(2) -0.008(2) 0.0038(19)
C(30) 0.040(3) 0.038(2) 0.032(3) -0.001(2) -0.011(2) 0.018(2)
C(31) 0.037(3) 0.034(2) 0.025(2) -0.004(2) -0.004(2) 0.010(2)
C(32) 0.034(2) 0.031(2) 0.016(2) 0.004(2) -0.002(2) 0.000(2)
C(33) 0.022(2) 0.022(2) 0.025(2) -0.0016(19) 0.000(2) 0.0052(19)
C(34) 0.025(2) 0.029(2) 0.030(2) 0.001(2) 0.004(2) 0.0026(19)
C(35) 0.032(3) 0.038(2) 0.039(3) -0.004(2) 0.002(2) -0.002(2)
C(36) 0.038(3) 0.030(2) 0.044(3) -0.004(2) 0.003(3) 0.007(2)
C(37) 0.049(4) 0.035(3) 0.044(3) 0.001(2) 0.011(3) 0.009(2)
C(38) 0.033(3) 0.032(2) 0.032(2) -0.002(2) 0.006(2) 0.004(2)
C(39) 0.020(2) 0.028(2) 0.015(2) -0.0040(19) 0.0036(19) -0.0042(17)
C(40) 0.023(2) 0.027(2) 0.020(2) 0.001(2) -0.001(2) -0.0010(18)
C(41) 0.038(3) 0.031(2) 0.014(2) 0.004(2) -0.003(2) 0.0063(19)
C(42) 0.026(3) 0.042(2) 0.015(2) -0.005(2) 0.003(2) -0.005(2)
C(43) 0.024(2) 0.031(2) 0.022(2) -0.003(2) 0.003(2) -0.007(2)
C(44) 0.024(2) 0.026(2) 0.024(2) 0.001(2) 0.002(2) 0.0028(19)
C(45) 0.025(2) 0.035(2) 0.016(2) -0.002(2) 0.001(2) 0.0006(19)
C(46) 0.032(3) 0.030(2) 0.015(2) 0.004(2) 0.000(2) 0.0037(18)
C(47) 0.039(3) 0.039(2) 0.035(2) -0.007(2) 0.003(2) -0.010(2)
C(48) 0.046(4) 0.041(3) 0.036(3) -0.003(2) 0.000(2) -0.007(2)
C(49) 0.046(3) 0.036(2) 0.020(2) 0.001(2) 0.003(2) -0.001(2)
C(50) 0.036(3) 0.043(3) 0.028(2) 0.002(2) 0.013(2) -0.003(2)
C(51) 0.031(3) 0.033(2) 0.030(2) -0.002(2) 0.004(2) -0.003(2)
C(52) 0.024(2) 0.036(2) 0.018(2) -0.001(2) 0.0032(19) -0.004(2)
C(53) 0.029(2) 0.032(2) 0.019(2) 0.001(2) -0.003(2) -0.0058(19)
C(54) 0.042(3) 0.041(3) 0.017(2) 0.002(2) -0.000(2) 0.003(2)
C(55) 0.032(3) 0.097(4) 0.029(3) -0.011(3) -0.001(2) -0.016(3)
C(56) 0.033(4) 0.119(6) 0.044(4) -0.012(3) -0.006(3) -0.009(3)
C(57) 0.039(4) 0.071(4) 0.042(3) -0.020(3) -0.013(3) 0.003(3)
C(58) 0.058(4) 0.042(3) 0.032(3) -0.001(3) -0.009(3) -0.004(2)
C(59) 0.041(3) 0.032(2) 0.029(2) -0.005(2) -0.009(2) 0.001(2)
C(60) 0.030(2) 0.032(2) 0.021(2) 0.003(2) -0.002(2) -0.005(2)
C(61) 0.051(4) 0.094(5) 0.044(4) 0.004(4) -0.006(3) -0.008(3)
C(62) 0.066(6) 0.104(6) 0.092(6) 0.003(5) -0.010(5) -0.023(5)
C(63) 0.061(6) 0.078(5) 0.110(7) -0.002(4) 0.020(5) 0.006(5)
C(64) 0.070(5) 0.063(4) 0.075(5) -0.012(4) 0.020(4) -0.014(3)
C(65) 0.058(5) 0.065(4) 0.084(5) -0.006(3) 0.008(4) -0.020(4)
C(66) 0.078(6) 0.059(4) 0.065(4) 0.003(3) 0.013(4) 0.002(3)
C(67) 0.071(6) 0.106(6) 0.070(5) 0.002(5) 0.013(4) -0.021(4)
C(68) 0.075(6) 0.096(6) 0.049(4) -0.001(4) 0.000(4) -0.003(3)
C(69) 0.093(10) 0.065(6) 0.145(10) -0.024(8) -0.051(9) 0.051(6)
C(70) 0.145(12) 0.061(7) 0.129(9) -0.021(8) -0.057(10) 0.017(6)
C(71) 0.069(8) 0.047(6) 0.066(6) 0.018(5) -0.035(6) 0.011(5)
C(72) 0.023(5) 0.044(5) 0.062(6) 0.012(4) -0.008(5) 0.022(4)
Li(1) 0.068(7) 0.027(4) 0.042(5) 0.002(4) 0.016(5) -0.003(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.290 2.459
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Li Li 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.102 0.094
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ru Ru -1.259 0.836
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
P(1) Ru(1) P(2) 88.90(4) yes . .
P(1) Ru(1) O(1) 98.70(9) yes . .
P(1) Ru(1) O(3) 94.06(9) yes . .
P(1) Ru(1) N(1) 92.23(11) yes . .
P(1) Ru(1) N(2) 170.53(10) yes . .
P(2) Ru(1) O(1) 92.89(9) yes . .
P(2) Ru(1) O(3) 99.02(9) yes . .
P(2) Ru(1) N(1) 168.83(10) yes . .
P(2) Ru(1) N(2) 91.52(10) yes . .
O(1) Ru(1) O(3) 162.70(13) yes . .
O(1) Ru(1) N(1) 75.95(13) yes . .
O(1) Ru(1) N(2) 90.72(13) yes . .
O(3) Ru(1) N(1) 91.99(13) yes . .
O(3) Ru(1) N(2) 76.53(13) yes . .
N(1) Ru(1) N(2) 89.19(15) yes . .
Ru(1) P(1) C(1) 110.82(16) yes . .
Ru(1) P(1) C(7) 124.15(15) yes . .
Ru(1) P(1) C(13) 112.89(15) yes . .
C(1) P(1) C(7) 101.5(2) yes . .
C(1) P(1) C(13) 104.7(2) yes . .
C(7) P(1) C(13) 100.7(2) yes . .
Ru(1) P(2) C(32) 113.80(14) yes . .
Ru(1) P(2) C(33) 109.08(16) yes . .
Ru(1) P(2) C(39) 124.21(15) yes . .
C(32) P(2) C(33) 106.9(2) yes . .
C(32) P(2) C(39) 99.3(2) yes . .
C(33) P(2) C(39) 101.8(2) yes . .
Ru(1) O(1) C(52) 117.4(2) yes . .
C(52) O(2) Li(1) 131.7(4) yes . .
Ru(1) O(3) C(60) 117.5(2) yes . .
C(60) O(4) Li(1) 154.9(4) yes . 4_564
C(61) O(5) C(64) 107.5(5) yes . .
C(65) O(6) C(68) 105.8(6) yes . .
C(69) O(7) C(72) 105.8(9) yes . .
Ru(1) N(1) C(45) 104.4(2) yes . .
Ru(1) N(2) C(53) 107.9(2) yes . .
P(1) C(1) C(2) 123.0(3) yes . .
P(1) C(1) C(6) 117.1(3) yes . .
C(2) C(1) C(6) 119.5(4) yes . .
C(1) C(2) C(3) 119.3(4) yes . .
C(2) C(3) C(4) 120.9(4) yes . .
C(3) C(4) C(5) 119.5(4) yes . .
C(4) C(5) C(6) 121.3(4) yes . .
C(1) C(6) C(5) 119.5(4) yes . .
P(1) C(7) C(8) 119.5(3) yes . .
P(1) C(7) C(12) 121.0(3) yes . .
C(8) C(7) C(12) 119.6(4) yes . .
C(7) C(8) C(9) 120.6(4) yes . .
C(8) C(9) C(10) 119.5(4) yes . .
C(9) C(10) C(11) 120.0(4) yes . .
C(10) C(11) C(12) 121.2(4) yes . .
C(7) C(12) C(11) 119.0(4) yes . .
P(1) C(13) C(14) 119.7(3) yes . .
P(1) C(13) C(22) 120.2(3) yes . .
C(14) C(13) C(22) 119.8(4) yes . .
C(13) C(14) C(15) 120.4(4) yes . .
C(14) C(15) C(16) 121.7(4) yes . .
C(15) C(16) C(17) 122.6(4) yes . .
C(15) C(16) C(21) 119.0(4) yes . .
C(17) C(16) C(21) 118.4(4) yes . .
C(16) C(17) C(18) 121.5(4) yes . .
C(17) C(18) C(19) 120.1(4) yes . .
C(18) C(19) C(20) 121.2(4) yes . .
C(19) C(20) C(21) 120.6(4) yes . .
C(16) C(21) C(20) 118.1(4) yes . .
C(16) C(21) C(22) 119.3(4) yes . .
C(20) C(21) C(22) 122.6(4) yes . .
C(13) C(22) C(21) 119.8(3) yes . .
C(13) C(22) C(23) 121.8(3) yes . .
C(21) C(22) C(23) 118.3(4) yes . .
C(22) C(23) C(24) 118.1(4) yes . .
C(22) C(23) C(32) 120.4(4) yes . .
C(24) C(23) C(32) 121.4(4) yes . .
C(23) C(24) C(25) 123.8(4) yes . .
C(23) C(24) C(29) 119.0(4) yes . .
C(25) C(24) C(29) 117.2(4) yes . .
C(24) C(25) C(26) 122.6(4) yes . .
C(25) C(26) C(27) 120.3(4) yes . .
C(26) C(27) C(28) 119.9(5) yes . .
C(27) C(28) C(29) 120.7(5) yes . .
C(24) C(29) C(28) 119.2(4) yes . .
C(24) C(29) C(30) 118.8(5) yes . .
C(28) C(29) C(30) 121.9(4) yes . .
C(29) C(30) C(31) 120.5(4) yes . .
C(30) C(31) C(32) 122.3(4) yes . .
P(2) C(32) C(23) 121.6(3) yes . .
P(2) C(32) C(31) 120.3(3) yes . .
C(23) C(32) C(31) 118.0(4) yes . .
P(2) C(33) C(34) 121.4(3) yes . .
P(2) C(33) C(38) 119.5(3) yes . .
C(34) C(33) C(38) 118.0(4) yes . .
C(33) C(34) C(35) 120.6(4) yes . .
C(34) C(35) C(36) 120.4(5) yes . .
C(35) C(36) C(37) 120.3(5) yes . .
C(36) C(37) C(38) 120.0(5) yes . .
C(33) C(38) C(37) 120.7(4) yes . .
P(2) C(39) C(40) 121.3(3) yes . .
P(2) C(39) C(44) 120.5(3) yes . .
C(40) C(39) C(44) 118.2(4) yes . .
C(39) C(40) C(41) 120.6(4) yes . .
C(40) C(41) C(42) 120.0(4) yes . .
C(41) C(42) C(43) 120.0(4) yes . .
C(42) C(43) C(44) 119.7(4) yes . .
C(39) C(44) C(43) 121.4(4) yes . .
N(1) C(45) C(46) 117.5(4) yes . .
N(1) C(45) C(52) 106.3(3) yes . .
C(46) C(45) C(52) 116.2(3) yes . .
C(45) C(46) C(47) 118.1(4) yes . .
C(45) C(46) C(51) 123.5(4) yes . .
C(47) C(46) C(51) 118.4(4) yes . .
C(46) C(47) C(48) 121.0(5) yes . .
C(47) C(48) C(49) 119.7(5) yes . .
C(48) C(49) C(50) 119.8(5) yes . .
C(49) C(50) C(51) 120.5(5) yes . .
C(46) C(51) C(50) 120.6(4) yes . .
O(1) C(52) O(2) 123.8(4) yes . .
O(1) C(52) C(45) 114.0(3) yes . .
O(2) C(52) C(45) 122.1(4) yes . .
N(2) C(53) C(54) 115.4(4) yes . .
N(2) C(53) C(60) 108.9(3) yes . .
C(54) C(53) C(60) 116.0(4) yes . .
C(53) C(54) C(55) 123.2(4) yes . .
C(53) C(54) C(59) 118.7(4) yes . .
C(55) C(54) C(59) 118.0(5) yes . .
C(54) C(55) C(56) 122.0(5) yes . .
C(55) C(56) C(57) 118.4(6) yes . .
C(56) C(57) C(58) 120.0(6) yes . .
C(57) C(58) C(59) 121.2(5) yes . .
C(54) C(59) C(58) 120.3(5) yes . .
O(3) C(60) O(4) 122.2(4) yes . .
O(3) C(60) C(53) 116.3(4) yes . .
O(4) C(60) C(53) 121.3(4) yes . .
O(5) C(61) C(62) 106.3(5) yes . .
C(61) C(62) C(63) 104.1(6) yes . .
C(62) C(63) C(64) 99.9(6) yes . .
O(5) C(64) C(63) 108.3(6) yes . .
O(6) C(65) C(66) 106.2(6) yes . .
C(65) C(66) C(67) 101.6(6) yes . .
C(66) C(67) C(68) 106.3(7) yes . .
O(6) C(68) C(67) 106.5(6) yes . .
O(7) C(69) C(70) 110.9(11) yes . .
C(69) C(70) C(71) 101.4(13) yes . .
C(70) C(71) C(72) 98.5(10) yes . .
O(7) C(72) C(71) 108.9(8) yes . .
O(2) Li(1) O(4) 115.8(4) yes . 4_565
O(2) Li(1) O(8) 93.0(4) yes . .
O(2) Li(1) O(9) 116.4(5) yes . .
O(4) Li(1) O(8) 120.8(5) yes 4_565 .
O(4) Li(1) O(9) 108.3(5) yes 4_565 .
O(8) Li(1) O(9) 101.7(4) yes . .
Ru(1) N(1) H(1NA) 110.9 no . .
Ru(1) N(1) H(1NB) 110.9 no . .
C(45) N(1) H(1NA) 110.9 no . .
C(45) N(1) H(1NB) 110.9 no . .
H(1NA) N(1) H(1NB) 108.9 no . .
Ru(1) N(2) H(2NA) 110.1 no . .
Ru(1) N(2) H(2NB) 110.1 no . .
C(53) N(2) H(2NA) 110.1 no . .
C(53) N(2) H(2NB) 110.1 no . .
H(2NA) N(2) H(2NB) 108.4 no . .
C(1) C(2) H(2) 120.4 no . .
C(3) C(2) H(2) 120.3 no . .
C(2) C(3) H(3) 119.6 no . .
C(4) C(3) H(3) 119.6 no . .
C(3) C(4) H(4) 120.3 no . .
C(5) C(4) H(4) 120.3 no . .
C(4) C(5) H(5) 119.3 no . .
C(6) C(5) H(5) 119.3 no . .
C(1) C(6) H(6) 120.3 no . .
C(5) C(6) H(6) 120.3 no . .
C(7) C(8) H(8) 119.7 no . .
C(9) C(8) H(8) 119.7 no . .
C(8) C(9) H(9) 120.2 no . .
C(10) C(9) H(9) 120.2 no . .
C(9) C(10) H(10) 120.0 no . .
C(11) C(10) H(10) 120.0 no . .
C(10) C(11) H(11) 119.4 no . .
C(12) C(11) H(11) 119.4 no . .
C(7) C(12) H(12) 120.5 no . .
C(11) C(12) H(12) 120.5 no . .
C(13) C(14) H(14) 119.8 no . .
C(15) C(14) H(14) 119.8 no . .
C(14) C(15) H(15) 119.2 no . .
C(16) C(15) H(15) 119.2 no . .
C(16) C(17) H(17) 119.3 no . .
C(18) C(17) H(17) 119.3 no . .
C(17) C(18) H(18) 119.9 no . .
C(19) C(18) H(18) 119.9 no . .
C(18) C(19) H(19) 119.4 no . .
C(20) C(19) H(19) 119.4 no . .
C(19) C(20) H(20) 119.7 no . .
C(21) C(20) H(20) 119.7 no . .
C(24) C(25) H(25) 118.7 no . .
C(26) C(25) H(25) 118.7 no . .
C(25) C(26) H(26) 119.8 no . .
C(27) C(26) H(26) 119.8 no . .
C(26) C(27) H(27) 120.1 no . .
C(28) C(27) H(27) 120.1 no . .
C(27) C(28) H(28) 119.7 no . .
C(29) C(28) H(28) 119.6 no . .
C(29) C(30) H(30) 119.7 no . .
C(31) C(30) H(30) 119.7 no . .
C(30) C(31) H(31) 118.9 no . .
C(32) C(31) H(31) 118.9 no . .
C(33) C(34) H(34) 119.7 no . .
C(35) C(34) H(34) 119.7 no . .
C(34) C(35) H(35) 119.8 no . .
C(36) C(35) H(35) 119.8 no . .
C(35) C(36) H(36) 119.9 no . .
C(37) C(36) H(36) 119.9 no . .
C(36) C(37) H(37) 120.0 no . .
C(38) C(37) H(37) 120.0 no . .
C(33) C(38) H(38) 119.7 no . .
C(37) C(38) H(38) 119.7 no . .
C(39) C(40) H(40) 119.7 no . .
C(41) C(40) H(40) 119.7 no . .
C(40) C(41) H(41) 120.0 no . .
C(42) C(41) H(41) 120.0 no . .
C(41) C(42) H(42) 120.0 no . .
C(43) C(42) H(42) 120.0 no . .
C(42) C(43) H(43) 120.2 no . .
C(44) C(43) H(43) 120.1 no . .
C(39) C(44) H(44) 119.3 no . .
C(43) C(44) H(44) 119.3 no . .
N(1) C(45) H(45) 105.2 no . .
C(46) C(45) H(45) 105.2 no . .
C(52) C(45) H(45) 105.2 no . .
C(46) C(47) H(47) 119.5 no . .
C(48) C(47) H(47) 119.5 no . .
C(47) C(48) H(48) 120.1 no . .
C(49) C(48) H(48) 120.1 no . .
C(48) C(49) H(49) 120.1 no . .
C(50) C(49) H(49) 120.1 no . .
C(49) C(50) H(50) 119.8 no . .
C(51) C(50) H(50) 119.8 no . .
C(46) C(51) H(51) 119.7 no . .
C(50) C(51) H(51) 119.7 no . .
N(2) C(53) H(53) 105.1 no . .
C(54) C(53) H(53) 105.1 no . .
C(60) C(53) H(53) 105.1 no . .
C(54) C(55) H(55) 119.0 no . .
C(56) C(55) H(55) 119.0 no . .
C(55) C(56) H(56) 120.8 no . .
C(57) C(56) H(56) 120.8 no . .
C(56) C(57) H(57) 120.0 no . .
C(58) C(57) H(57) 120.0 no . .
C(57) C(58) H(58) 119.4 no . .
C(59) C(58) H(58) 119.4 no . .
C(54) C(59) H(59) 119.8 no . .
C(58) C(59) H(59) 119.8 no . .
O(5) C(61) H(61A) 110.5 no . .
O(5) C(61) H(61B) 110.5 no . .
C(62) C(61) H(61A) 110.5 no . .
C(62) C(61) H(61B) 110.5 no . .
H(61A) C(61) H(61B) 108.6 no . .
C(61) C(62) H(62A) 110.9 no . .
C(61) C(62) H(62B) 110.9 no . .
C(63) C(62) H(62A) 110.9 no . .
C(63) C(62) H(62B) 110.9 no . .
H(62A) C(62) H(62B) 109.0 no . .
C(62) C(63) H(63A) 111.8 no . .
C(62) C(63) H(63B) 111.8 no . .
C(64) C(63) H(63A) 111.8 no . .
C(64) C(63) H(63B) 111.8 no . .
H(63A) C(63) H(63B) 109.5 no . .
O(5) C(64) H(64A) 110.0 no . .
O(5) C(64) H(64B) 110.0 no . .
C(63) C(64) H(64A) 110.0 no . .
C(63) C(64) H(64B) 110.0 no . .
H(64A) C(64) H(64B) 108.4 no . .
O(6) C(65) H(65A) 110.5 no . .
O(6) C(65) H(65B) 110.5 no . .
C(66) C(65) H(65A) 110.5 no . .
C(66) C(65) H(65B) 110.5 no . .
H(65A) C(65) H(65B) 108.7 no . .
C(65) C(66) H(66A) 111.5 no . .
C(65) C(66) H(66B) 111.4 no . .
C(67) C(66) H(66A) 111.4 no . .
C(67) C(66) H(66B) 111.5 no . .
H(66A) C(66) H(66B) 109.3 no . .
C(66) C(67) H(67A) 110.5 no . .
C(66) C(67) H(67B) 110.5 no . .
C(68) C(67) H(67A) 110.5 no . .
C(68) C(67) H(67B) 110.5 no . .
H(67A) C(67) H(67B) 108.7 no . .
O(6) C(68) H(68A) 110.4 no . .
O(6) C(68) H(68B) 110.4 no . .
C(67) C(68) H(68A) 110.4 no . .
C(67) C(68) H(68B) 110.4 no . .
H(68A) C(68) H(68B) 108.6 no . .
O(7) C(69) H(69A) 109.5 no . .
O(7) C(69) H(69B) 109.5 no . .
C(70) C(69) H(69A) 109.5 no . .
C(70) C(69) H(69B) 109.5 no . .
H(69A) C(69) H(69B) 108.0 no . .
C(69) C(70) H(70A) 111.5 no . .
C(69) C(70) H(70B) 111.5 no . .
C(71) C(70) H(70A) 111.5 no . .
C(71) C(70) H(70B) 111.5 no . .
H(70A) C(70) H(70B) 109.3 no . .
C(70) C(71) H(71A) 112.1 no . .
C(70) C(71) H(71B) 112.1 no . .
C(72) C(71) H(71A) 112.1 no . .
C(72) C(71) H(71B) 112.1 no . .
H(71A) C(71) H(71B) 109.7 no . .
O(7) C(72) H(72A) 109.9 no . .
O(7) C(72) H(72B) 109.9 no . .
C(71) C(72) H(72A) 109.9 no . .
C(71) C(72) H(72B) 109.9 no . .
H(72A) C(72) H(72B) 108.3 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Ru(1) P(1) 2.2843(12) yes .
Ru(1) P(2) 2.2703(12) yes .
Ru(1) O(1) 2.101(3) yes .
Ru(1) O(3) 2.113(3) yes .
Ru(1) N(1) 2.193(4) yes .
Ru(1) N(2) 2.178(4) yes .
P(1) C(1) 1.860(4) yes .
P(1) C(7) 1.838(4) yes .
P(1) C(13) 1.844(4) yes .
P(2) C(32) 1.845(5) yes .
P(2) C(33) 1.852(4) yes .
P(2) C(39) 1.826(4) yes .
O(1) C(52) 1.303(5) yes .
O(2) C(52) 1.230(5) yes .
O(2) Li(1) 1.918(9) yes .
O(3) C(60) 1.302(6) yes .
O(4) C(60) 1.239(5) yes .
O(4) Li(1) 1.967(10) yes 4_564
O(5) C(61) 1.453(8) yes .
O(5) C(64) 1.429(9) yes .
O(6) C(65) 1.439(9) yes .
O(6) C(68) 1.410(10) yes .
O(7) C(69) 1.398(16) yes .
O(7) C(72) 1.433(13) yes .
O(8) Li(1) 2.095(12) yes .
O(9) Li(1) 1.974(11) yes .
N(1) C(45) 1.486(6) yes .
N(2) C(53) 1.490(5) yes .
C(1) C(2) 1.399(6) yes .
C(1) C(6) 1.410(6) yes .
C(2) C(3) 1.393(6) yes .
C(3) C(4) 1.391(7) yes .
C(4) C(5) 1.372(7) yes .
C(5) C(6) 1.384(7) yes .
C(7) C(8) 1.391(7) yes .
C(7) C(12) 1.404(6) yes .
C(8) C(9) 1.381(7) yes .
C(9) C(10) 1.395(7) yes .
C(10) C(11) 1.374(7) yes .
C(11) C(12) 1.384(7) yes .
C(13) C(14) 1.430(6) yes .
C(13) C(22) 1.394(6) yes .
C(14) C(15) 1.366(6) yes .
C(15) C(16) 1.408(7) yes .
C(16) C(17) 1.421(7) yes .
C(16) C(21) 1.428(6) yes .
C(17) C(18) 1.362(7) yes .
C(18) C(19) 1.384(7) yes .
C(19) C(20) 1.369(7) yes .
C(20) C(21) 1.426(6) yes .
C(21) C(22) 1.439(6) yes .
C(22) C(23) 1.512(6) yes .
C(23) C(24) 1.431(7) yes .
C(23) C(32) 1.380(6) yes .
C(24) C(25) 1.406(6) yes .
C(24) C(29) 1.429(6) yes .
C(25) C(26) 1.358(7) yes .
C(26) C(27) 1.396(7) yes .
C(27) C(28) 1.375(8) yes .
C(28) C(29) 1.418(8) yes .
C(29) C(30) 1.427(7) yes .
C(30) C(31) 1.349(8) yes .
C(31) C(32) 1.442(6) yes .
C(33) C(34) 1.402(6) yes .
C(33) C(38) 1.396(7) yes .
C(34) C(35) 1.379(7) yes .
C(35) C(36) 1.378(8) yes .
C(36) C(37) 1.369(8) yes .
C(37) C(38) 1.392(7) yes .
C(39) C(40) 1.390(6) yes .
C(39) C(44) 1.395(6) yes .
C(40) C(41) 1.401(6) yes .
C(41) C(42) 1.365(7) yes .
C(42) C(43) 1.403(6) yes .
C(43) C(44) 1.369(6) yes .
C(45) C(46) 1.507(6) yes .
C(45) C(52) 1.531(6) yes .
C(46) C(47) 1.402(7) yes .
C(46) C(51) 1.379(7) yes .
C(47) C(48) 1.382(7) yes .
C(48) C(49) 1.367(8) yes .
C(49) C(50) 1.394(7) yes .
C(50) C(51) 1.375(7) yes .
C(53) C(54) 1.508(7) yes .
C(53) C(60) 1.515(6) yes .
C(54) C(55) 1.370(8) yes .
C(54) C(59) 1.398(7) yes .
C(55) C(56) 1.397(9) yes .
C(56) C(57) 1.390(9) yes .
C(57) C(58) 1.360(9) yes .
C(58) C(59) 1.373(8) yes .
C(61) C(62) 1.479(11) yes .
C(62) C(63) 1.532(13) yes .
C(63) C(64) 1.476(11) yes .
C(65) C(66) 1.493(11) yes .
C(66) C(67) 1.545(11) yes .
C(67) C(68) 1.482(12) yes .
C(69) C(70) 1.41(2) yes .
C(70) C(71) 1.59(2) yes .
C(71) C(72) 1.435(15) yes .
N(1) H(1NA) 0.920 no .
N(1) H(1NB) 0.920 no .
N(2) H(2NA) 0.920 no .
N(2) H(2NB) 0.920 no .
C(2) H(2) 0.950 no .
C(3) H(3) 0.950 no .
C(4) H(4) 0.950 no .
C(5) H(5) 0.950 no .
C(6) H(6) 0.950 no .
C(8) H(8) 0.950 no .
C(9) H(9) 0.950 no .
C(10) H(10) 0.950 no .
C(11) H(11) 0.950 no .
C(12) H(12) 0.950 no .
C(14) H(14) 0.950 no .
C(15) H(15) 0.950 no .
C(17) H(17) 0.950 no .
C(18) H(18) 0.950 no .
C(19) H(19) 0.950 no .
C(20) H(20) 0.950 no .
C(25) H(25) 0.950 no .
C(26) H(26) 0.950 no .
C(27) H(27) 0.950 no .
C(28) H(28) 0.950 no .
C(30) H(30) 0.950 no .
C(31) H(31) 0.950 no .
C(34) H(34) 0.950 no .
C(35) H(35) 0.950 no .
C(36) H(36) 0.950 no .
C(37) H(37) 0.950 no .
C(38) H(38) 0.950 no .
C(40) H(40) 0.950 no .
C(41) H(41) 0.950 no .
C(42) H(42) 0.950 no .
C(43) H(43) 0.950 no .
C(44) H(44) 0.950 no .
C(45) H(45) 1.000 no .
C(47) H(47) 0.950 no .
C(48) H(48) 0.950 no .
C(49) H(49) 0.950 no .
C(50) H(50) 0.950 no .
C(51) H(51) 0.950 no .
C(53) H(53) 1.000 no .
C(55) H(55) 0.950 no .
C(56) H(56) 0.950 no .
C(57) H(57) 0.950 no .
C(58) H(58) 0.950 no .
C(59) H(59) 0.950 no .
C(61) H(61A) 0.990 no .
C(61) H(61B) 0.990 no .
C(62) H(62A) 0.990 no .
C(62) H(62B) 0.990 no .
C(63) H(63A) 0.990 no .
C(63) H(63B) 0.990 no .
C(64) H(64A) 0.990 no .
C(64) H(64B) 0.990 no .
C(65) H(65A) 0.990 no .
C(65) H(65B) 0.990 no .
C(66) H(66A) 0.990 no .
C(66) H(66B) 0.990 no .
C(67) H(67A) 0.990 no .
C(67) H(67B) 0.990 no .
C(68) H(68A) 0.990 no .
C(68) H(68B) 0.990 no .
C(69) H(69A) 0.990 no .
C(69) H(69B) 0.990 no .
C(70) H(70A) 0.990 no .
C(70) H(70B) 0.990 no .
C(71) H(71A) 0.990 no .
C(71) H(71B) 0.990 no .
C(72) H(72A) 0.990 no .
C(72) H(72B) 0.990 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Br(1) O(8) 3.523(4) .
Br(1) N(1) 3.471(4) .
Br(1) N(2) 3.369(3) .
O(4) C(68) 3.497(9) 4_564
O(5) O(8) 2.812(6) .
O(5) C(37) 3.400(8) .
O(5) C(66) 3.357(9) .
O(6) O(9) 2.807(7) .
O(6) C(72) 3.577(13) .
O(7) O(9) 2.820(10) .
O(8) Br(1) 3.523(4) .
O(8) O(5) 2.812(6) .
O(8) C(64) 3.380(8) .
O(9) O(6) 2.807(7) .
O(9) O(7) 2.820(10) .
O(9) C(68) 3.438(9) .
O(9) C(69) 3.46(2) .
O(9) C(72) 3.460(12) .
N(1) Br(1) 3.471(4) .
N(2) Br(1) 3.369(3) .
C(3) C(42) 3.535(6) 3_655
C(4) C(9) 3.426(7) 2_466
C(4) C(10) 3.531(7) 2_466
C(4) C(42) 3.439(7) 3_655
C(4) C(43) 3.439(7) 3_655
C(5) C(9) 3.572(7) 2_466
C(5) C(10) 3.570(7) 2_466
C(5) C(43) 3.508(7) 3_655
C(9) C(4) 3.426(7) 2_566
C(9) C(5) 3.572(7) 2_566
C(10) C(4) 3.531(7) 2_566
C(10) C(5) 3.570(7) 2_566
C(29) C(66) 3.575(8) 2_556
C(30) C(66) 3.562(9) 2_556
C(36) C(61) 3.590(9) .
C(37) O(5) 3.400(8) .
C(37) C(61) 3.535(9) .
C(42) C(3) 3.535(6) 3_645
C(42) C(4) 3.439(7) 3_645
C(43) C(4) 3.439(7) 3_645
C(43) C(5) 3.508(7) 3_645
C(61) C(36) 3.590(9) .
C(61) C(37) 3.535(9) .
C(64) O(8) 3.380(8) .
C(64) C(66) 3.594(11) .
C(66) O(5) 3.357(9) .
C(66) C(29) 3.575(8) 2_456
C(66) C(30) 3.562(9) 2_456
C(66) C(64) 3.594(11) .
C(68) O(4) 3.497(9) 4_565
C(68) O(9) 3.438(9) .
C(69) O(9) 3.46(2) .
C(72) O(6) 3.577(13) .
C(72) O(9) 3.460(12) .
Br(1) H(1NB) 2.579 .
Br(1) H(2NA) 3.526 .
Br(1) H(2NB) 2.518 .
Br(1) H(3) 3.079 2_466
Br(1) H(27) 3.501 1_455
Br(1) H(41) 3.285 4_565
Br(1) H(42) 3.035 4_565
Br(1) H(51) 2.936 .
Br(1) H(55) 2.863 .
Br(1) H(61B) 3.172 .
Br(1) H(63A) 3.276 .
O(3) H(67A) 3.575 4_564
O(3) H(68A) 3.178 4_564
O(4) H(67A) 3.426 4_564
O(4) H(68A) 2.558 4_564
O(5) H(30) 3.301 2_456
O(5) H(37) 2.878 .
O(5) H(66B) 2.400 .
O(6) H(57) 3.340 2_556
O(6) H(62A) 3.239 2_556
O(6) H(62B) 3.498 2_556
O(6) H(71B) 3.492 .
O(6) H(72B) 2.692 .
O(7) H(30) 2.923 .
O(7) H(36) 3.389 2_556
O(7) H(61A) 3.062 2_556
O(7) H(62A) 3.522 2_556
O(8) H(61B) 3.350 .
O(8) H(64A) 2.986 .
O(8) H(66B) 3.316 .
O(8) H(67A) 3.206 .
O(9) H(62A) 3.271 2_556
O(9) H(68A) 3.088 .
O(9) H(69A) 3.054 .
O(9) H(72B) 3.157 .
N(2) H(61B) 3.273 .
C(1) H(43) 3.464 3_655
C(2) H(43) 3.571 3_655
C(2) H(50) 3.587 2_566
C(3) H(9) 3.527 2_466
C(3) H(26) 3.403 2_466
C(3) H(42) 2.781 3_655
C(3) H(43) 3.267 3_655
C(4) H(9) 2.776 2_466
C(4) H(10) 2.990 2_466
C(4) H(42) 2.821 3_655
C(4) H(43) 2.827 3_655
C(5) H(9) 2.936 2_466
C(5) H(10) 2.926 2_466
C(5) H(19) 3.536 3_655
C(5) H(43) 2.657 3_655
C(5) H(67B) 3.025 4_564
C(5) H(68B) 3.139 4_564
C(6) H(43) 3.023 3_655
C(6) H(67B) 3.103 4_564
C(6) H(68B) 3.546 4_564
C(9) H(4) 3.143 2_566
C(9) H(5) 3.434 2_566
C(10) H(4) 3.031 2_566
C(10) H(5) 3.124 2_566
C(10) H(18) 3.231 4_665
C(10) H(19) 3.456 4_665
C(11) H(18) 3.513 4_665
C(11) H(69A) 3.522 .
C(11) H(69B) 3.332 .
C(13) H(49) 3.449 2_566
C(14) H(49) 3.072 2_566
C(14) H(50) 3.309 2_566
C(14) H(67A) 3.590 4_564
C(15) H(35) 3.541 3_655
C(15) H(49) 2.778 2_566
C(15) H(64A) 3.092 4_564
C(16) H(35) 3.576 3_655
C(16) H(49) 2.943 2_566
C(17) H(28) 3.254 4_664
C(17) H(35) 3.254 3_655
C(17) H(63A) 3.378 4_564
C(17) H(63B) 3.326 4_564
C(18) H(4) 3.273 3_645
C(18) H(10) 3.274 4_664
C(18) H(28) 3.205 4_664
C(18) H(69B) 3.016 4_664
C(19) H(4) 3.496 3_645
C(19) H(5) 3.426 3_645
C(19) H(10) 3.213 4_664
C(19) H(65A) 3.528 2_556
C(19) H(69B) 3.478 4_664
C(20) H(65A) 3.189 2_556
C(20) H(66A) 3.253 2_556
C(21) H(49) 3.356 2_566
C(23) H(66A) 3.223 2_556
C(24) H(65A) 3.477 2_556
C(24) H(66A) 3.167 2_556
C(25) H(48) 3.449 2_566
C(25) H(65A) 3.573 2_556
C(26) H(3) 3.449 2_566
C(26) H(4) 3.276 2_566
C(26) H(48) 3.498 2_566
C(27) H(4) 3.114 2_566
C(27) H(18) 3.255 4_665
C(27) H(62B) 3.337 1_655
C(27) H(63A) 3.205 1_655
C(27) H(63B) 3.538 1_655
C(27) H(65A) 3.588 2_556
C(27) H(65B) 3.355 2_556
C(28) H(17) 3.413 4_665
C(28) H(18) 2.874 4_665
C(28) H(36) 3.304 2_556
C(28) H(63B) 3.372 1_655
C(28) H(65A) 3.526 2_556
C(28) H(65B) 2.946 2_556
C(29) H(65A) 3.483 2_556
C(29) H(65B) 3.256 2_556
C(29) H(66A) 3.059 2_556
C(30) H(36) 3.438 2_556
C(30) H(64B) 3.492 2_556
C(30) H(66A) 3.045 2_556
C(30) H(66B) 3.324 2_556
C(31) H(64B) 2.978 2_556
C(31) H(66A) 3.102 2_556
C(32) H(66A) 3.191 2_556
C(33) H(64B) 3.341 2_556
C(34) H(15) 3.444 3_645
C(35) H(15) 3.341 3_645
C(35) H(17) 3.121 3_645
C(35) H(63B) 3.376 2_556
C(35) H(72A) 3.243 2_456
C(36) H(17) 3.149 3_645
C(36) H(28) 3.123 2_456
C(36) H(30) 3.512 2_456
C(36) H(61A) 2.941 .
C(36) H(63B) 2.863 2_556
C(36) H(72A) 3.400 2_456
C(37) H(61A) 3.238 .
C(37) H(61B) 3.424 .
C(37) H(62A) 3.532 2_556
C(37) H(63B) 2.929 2_556
C(37) H(65B) 3.500 .
C(38) H(63B) 3.528 2_556
C(38) H(64B) 3.426 2_556
C(42) H(3) 3.582 3_645
C(42) H(4) 3.452 3_645
C(43) H(67B) 3.188 2_556
C(44) H(66A) 3.331 2_556
C(44) H(67B) 3.334 2_556
C(47) H(9) 3.480 2_466
C(47) H(71A) 3.403 3_656
C(48) H(8) 3.425 2_466
C(48) H(25) 3.104 2_466
C(48) H(26) 3.487 2_466
C(48) H(70B) 3.075 3_656
C(48) H(71A) 3.074 3_656
C(49) H(8) 2.905 2_466
C(49) H(25) 3.197 2_466
C(49) H(70B) 3.584 3_656
C(50) H(8) 2.858 2_466
C(51) H(8) 3.378 2_466
C(55) H(61B) 3.206 .
C(55) H(62B) 3.383 .
C(55) H(70A) 3.138 4_564
C(56) H(62B) 3.163 .
C(56) H(65A) 3.460 2_456
C(56) H(69A) 3.487 4_564
C(56) H(70A) 2.974 4_564
C(56) H(72B) 3.478 2_456
C(57) H(69A) 3.477 4_564
C(57) H(71A) 3.482 2_456
C(57) H(72A) 3.583 2_456
C(57) H(72B) 3.119 2_456
C(58) H(71A) 3.040 2_456
C(58) H(72A) 3.379 2_456
C(58) H(72B) 3.506 2_456
C(59) H(72A) 3.531 2_456
C(60) H(68A) 3.168 4_564
C(61) H(2NA) 3.560 .
C(61) H(30) 3.543 2_456
C(61) H(36) 3.463 .
C(61) H(37) 3.393 .
C(61) H(72A) 3.599 2_456
C(61) H(72B) 3.581 2_456
C(62) H(27) 3.458 1_455
C(62) H(65B) 3.119 2_456
C(62) H(72B) 3.465 2_456
C(63) H(15) 3.504 4_565
C(63) H(17) 2.947 4_565
C(63) H(27) 3.022 1_455
C(63) H(28) 3.400 1_455
C(64) H(15) 3.082 4_565
C(64) H(31) 3.379 2_456
C(64) H(66B) 2.847 .
C(64) H(67A) 3.561 .
C(65) H(20) 3.122 2_456
C(65) H(37) 3.398 .
C(65) H(56) 3.418 2_556
C(65) H(62A) 3.412 2_556
C(65) H(62B) 3.303 2_556
C(66) H(20) 3.036 2_456
C(66) H(37) 3.492 .
C(66) H(44) 3.343 2_456
C(66) H(64A) 3.410 .
C(66) H(64B) 3.408 .
C(67) H(5) 3.302 4_565
C(67) H(6) 3.231 4_565
C(67) H(14) 3.445 4_565
C(67) H(20) 3.575 2_456
C(67) H(43) 3.515 2_456
C(67) H(44) 3.435 2_456
C(67) H(64A) 3.492 .
C(68) H(5) 3.071 4_565
C(68) H(6) 3.304 4_565
C(68) H(57) 3.479 2_556
C(68) H(71B) 3.413 .
C(68) H(72B) 3.499 .
C(69) H(11) 2.984 .
C(70) H(48) 2.898 3_646
C(71) H(48) 3.158 3_646
C(71) H(58) 3.522 2_556
C(72) H(61A) 3.057 2_556
Li(1) H(67A) 3.577 .
Li(1) H(68A) 3.228 .
H(1NA) H(9) 3.252 2_466
H(1NB) Br(1) 2.579 .
H(2NA) Br(1) 3.526 .
H(2NA) C(61) 3.560 .
H(2NA) H(61B) 2.693 .
H(2NB) Br(1) 2.518 .
H(2NB) H(61B) 3.050 .
H(3) Br(1) 3.079 2_566
H(3) C(26) 3.449 2_466
H(3) C(42) 3.582 3_655
H(3) H(26) 2.799 2_466
H(3) H(27) 3.357 2_466
H(3) H(42) 2.700 3_655
H(4) C(9) 3.143 2_466
H(4) C(10) 3.031 2_466
H(4) C(18) 3.273 3_655
H(4) C(19) 3.496 3_655
H(4) C(26) 3.276 2_466
H(4) C(27) 3.114 2_466
H(4) C(42) 3.452 3_655
H(4) H(9) 2.715 2_466
H(4) H(10) 2.498 2_466
H(4) H(18) 2.971 3_655
H(4) H(19) 3.363 3_655
H(4) H(26) 3.248 2_466
H(4) H(27) 2.997 2_466
H(4) H(42) 2.798 3_655
H(4) H(43) 3.212 3_655
H(5) C(9) 3.434 2_466
H(5) C(10) 3.124 2_466
H(5) C(19) 3.426 3_655
H(5) C(67) 3.302 4_564
H(5) C(68) 3.071 4_564
H(5) H(9) 3.015 2_466
H(5) H(10) 2.374 2_466
H(5) H(19) 2.812 3_655
H(5) H(43) 2.919 3_655
H(5) H(67B) 2.670 4_564
H(5) H(68A) 3.360 4_564
H(5) H(68B) 2.314 4_564
H(6) C(67) 3.231 4_564
H(6) C(68) 3.304 4_564
H(6) H(43) 3.489 3_655
H(6) H(67A) 3.120 4_564
H(6) H(67B) 2.848 4_564
H(6) H(68A) 3.026 4_564
H(6) H(68B) 3.165 4_564
H(8) C(48) 3.425 2_566
H(8) C(49) 2.905 2_566
H(8) C(50) 2.858 2_566
H(8) C(51) 3.378 2_566
H(8) H(49) 3.141 2_566
H(8) H(50) 3.045 2_566
H(9) C(3) 3.527 2_566
H(9) C(4) 2.776 2_566
H(9) C(5) 2.936 2_566
H(9) C(47) 3.480 2_566
H(9) H(1NA) 3.252 2_566
H(9) H(4) 2.715 2_566
H(9) H(5) 3.015 2_566
H(10) C(4) 2.990 2_566
H(10) C(5) 2.926 2_566
H(10) C(18) 3.274 4_665
H(10) C(19) 3.213 4_665
H(10) H(4) 2.498 2_566
H(10) H(5) 2.374 2_566
H(10) H(18) 2.709 4_665
H(10) H(19) 2.576 4_665
H(10) H(68B) 3.520 3_656
H(11) C(69) 2.984 .
H(11) H(18) 3.226 4_665
H(11) H(19) 3.585 4_665
H(11) H(69A) 2.603 .
H(11) H(69B) 2.494 .
H(14) C(67) 3.445 4_564
H(14) H(43) 2.980 3_655
H(14) H(49) 3.545 2_566
H(14) H(50) 3.129 2_566
H(14) H(67A) 2.987 4_564
H(14) H(67B) 2.973 4_564
H(15) C(34) 3.444 3_655
H(15) C(35) 3.341 3_655
H(15) C(63) 3.504 4_564
H(15) C(64) 3.082 4_564
H(15) H(34) 3.376 3_655
H(15) H(35) 3.200 3_655
H(15) H(44) 3.509 3_655
H(15) H(49) 3.074 2_566
H(15) H(63A) 3.564 4_564
H(15) H(63B) 3.313 4_564
H(15) H(64A) 2.388 4_564
H(15) H(64B) 3.115 4_564
H(15) H(67A) 3.542 4_564
H(17) C(28) 3.413 4_664
H(17) C(35) 3.121 3_655
H(17) C(36) 3.149 3_655
H(17) C(63) 2.947 4_564
H(17) H(27) 3.318 4_664
H(17) H(28) 2.647 4_664
H(17) H(35) 2.901 3_655
H(17) H(36) 2.954 3_655
H(17) H(63A) 2.730 4_564
H(17) H(63B) 2.411 4_564
H(17) H(64A) 3.395 4_564
H(18) C(10) 3.231 4_664
H(18) C(11) 3.513 4_664
H(18) C(27) 3.255 4_664
H(18) C(28) 2.874 4_664
H(18) H(4) 2.971 3_645
H(18) H(10) 2.709 4_664
H(18) H(11) 3.226 4_664
H(18) H(27) 3.256 4_664
H(18) H(28) 2.552 4_664
H(18) H(69B) 2.671 4_664
H(19) C(5) 3.536 3_645
H(19) C(10) 3.456 4_664
H(19) H(4) 3.363 3_645
H(19) H(5) 2.812 3_645
H(19) H(10) 2.576 4_664
H(19) H(11) 3.585 4_664
H(19) H(56) 3.578 1_655
H(19) H(57) 3.002 1_655
H(19) H(65A) 3.106 2_556
H(19) H(67B) 3.480 2_556
H(19) H(68B) 2.993 2_556
H(19) H(69B) 3.488 4_664
H(20) C(65) 3.122 2_556
H(20) C(66) 3.036 2_556
H(20) C(67) 3.575 2_556
H(20) H(65A) 2.417 2_556
H(20) H(66A) 2.361 2_556
H(20) H(67B) 3.209 2_556
H(25) C(48) 3.104 2_566
H(25) C(49) 3.197 2_566
H(25) H(48) 2.768 2_566
H(25) H(49) 2.957 2_566
H(25) H(70B) 3.597 4_664
H(26) C(3) 3.403 2_566
H(26) C(48) 3.487 2_566
H(26) H(3) 2.799 2_566
H(26) H(4) 3.248 2_566
H(26) H(48) 2.886 2_566
H(26) H(56) 3.455 1_655
H(26) H(70A) 3.431 4_664
H(27) Br(1) 3.501 1_655
H(27) C(62) 3.458 1_655
H(27) C(63) 3.022 1_655
H(27) H(3) 3.357 2_566
H(27) H(4) 2.997 2_566
H(27) H(17) 3.318 4_665
H(27) H(18) 3.256 4_665
H(27) H(42) 3.560 4_665
H(27) H(62B) 2.925 1_655
H(27) H(63A) 2.391 1_655
H(27) H(63B) 3.063 1_655
H(28) C(17) 3.254 4_665
H(28) C(18) 3.205 4_665
H(28) C(36) 3.123 2_556
H(28) C(63) 3.400 1_655
H(28) H(17) 2.647 4_665
H(28) H(18) 2.552 4_665
H(28) H(36) 2.442 2_556
H(28) H(37) 3.491 2_556
H(28) H(63A) 3.309 1_655
H(28) H(63B) 2.735 1_655
H(28) H(65B) 3.027 2_556
H(30) O(5) 3.301 2_556
H(30) O(7) 2.923 .
H(30) C(36) 3.512 2_556
H(30) C(61) 3.543 2_556
H(30) H(36) 2.633 2_556
H(30) H(61A) 2.951 2_556
H(30) H(64B) 3.459 2_556
H(30) H(66A) 3.539 2_556
H(30) H(66B) 3.378 2_556
H(30) H(69B) 3.301 .
H(31) C(64) 3.379 2_556
H(31) H(62A) 3.232 2_556
H(31) H(64B) 2.514 2_556
H(34) H(15) 3.376 3_645
H(35) C(15) 3.541 3_645
H(35) C(16) 3.576 3_645
H(35) C(17) 3.254 3_645
H(35) H(15) 3.200 3_645
H(35) H(17) 2.901 3_645
H(35) H(70B) 3.245 2_456
H(35) H(72A) 2.854 2_456
H(36) O(7) 3.389 2_456
H(36) C(28) 3.304 2_456
H(36) C(30) 3.438 2_456
H(36) C(61) 3.463 .
H(36) H(17) 2.954 3_645
H(36) H(28) 2.442 2_456
H(36) H(30) 2.633 2_456
H(36) H(61A) 2.690 .
H(36) H(63B) 3.039 2_556
H(36) H(72A) 3.148 2_456
H(37) O(5) 2.878 .
H(37) C(61) 3.393 .
H(37) C(65) 3.398 .
H(37) C(66) 3.492 .
H(37) H(28) 3.491 2_456
H(37) H(61A) 3.240 .
H(37) H(61B) 3.436 .
H(37) H(62A) 3.304 2_556
H(37) H(63B) 3.120 2_556
H(37) H(65B) 2.724 .
H(37) H(66B) 2.773 .
H(41) Br(1) 3.285 4_564
H(41) H(63A) 3.231 4_564
H(41) H(64A) 3.157 4_564
H(42) Br(1) 3.035 4_564
H(42) C(3) 2.781 3_645
H(42) C(4) 2.821 3_645
H(42) H(3) 2.700 3_645
H(42) H(4) 2.798 3_645
H(42) H(27) 3.560 4_664
H(43) C(1) 3.464 3_645
H(43) C(2) 3.571 3_645
H(43) C(3) 3.267 3_645
H(43) C(4) 2.827 3_645
H(43) C(5) 2.657 3_645
H(43) C(6) 3.023 3_645
H(43) C(67) 3.515 2_556
H(43) H(4) 3.212 3_645
H(43) H(5) 2.919 3_645
H(43) H(6) 3.489 3_645
H(43) H(14) 2.980 3_645
H(43) H(67B) 2.537 2_556
H(44) C(66) 3.343 2_556
H(44) C(67) 3.435 2_556
H(44) H(15) 3.509 3_645
H(44) H(64B) 3.333 2_556
H(44) H(66A) 2.613 2_556
H(44) H(67B) 2.827 2_556
H(47) H(71A) 3.184 3_656
H(48) C(25) 3.449 2_466
H(48) C(26) 3.498 2_466
H(48) C(70) 2.898 3_656
H(48) C(71) 3.158 3_656
H(48) H(25) 2.768 2_466
H(48) H(26) 2.886 2_466
H(48) H(70A) 3.086 3_656
H(48) H(70B) 2.272 3_656
H(48) H(71A) 2.575 3_656
H(49) C(13) 3.449 2_466
H(49) C(14) 3.072 2_466
H(49) C(15) 2.778 2_466
H(49) C(16) 2.943 2_466
H(49) C(21) 3.356 2_466
H(49) H(8) 3.141 2_466
H(49) H(14) 3.545 2_466
H(49) H(15) 3.074 2_466
H(49) H(25) 2.957 2_466
H(49) H(70B) 3.298 3_656
H(50) C(2) 3.587 2_466
H(50) C(14) 3.309 2_466
H(50) H(8) 3.045 2_466
H(50) H(14) 3.129 2_466
H(51) Br(1) 2.936 .
H(55) Br(1) 2.863 .
H(55) H(61B) 2.918 .
H(55) H(62B) 3.199 .
H(55) H(70A) 3.154 4_564
H(56) C(65) 3.418 2_456
H(56) H(19) 3.578 1_455
H(56) H(26) 3.455 1_455
H(56) H(62B) 2.831 .
H(56) H(65A) 2.709 2_456
H(56) H(65B) 3.582 2_456
H(56) H(70A) 2.870 4_564
H(57) O(6) 3.340 2_456
H(57) C(68) 3.479 2_456
H(57) H(19) 3.002 1_455
H(57) H(65A) 3.370 2_456
H(57) H(68B) 2.787 2_456
H(57) H(71A) 3.450 2_456
H(57) H(72B) 3.135 2_456
H(58) C(71) 3.522 2_456
H(58) H(71A) 2.688 2_456
H(61A) O(7) 3.062 2_456
H(61A) C(36) 2.941 .
H(61A) C(37) 3.238 .
H(61A) C(72) 3.057 2_456
H(61A) H(30) 2.951 2_456
H(61A) H(36) 2.690 .
H(61A) H(37) 3.240 .
H(61A) H(72A) 2.728 2_456
H(61A) H(72B) 2.930 2_456
H(61B) Br(1) 3.172 .
H(61B) O(8) 3.350 .
H(61B) N(2) 3.273 .
H(61B) C(37) 3.424 .
H(61B) C(55) 3.206 .
H(61B) H(2NA) 2.693 .
H(61B) H(2NB) 3.050 .
H(61B) H(37) 3.436 .
H(61B) H(55) 2.918 .
H(62A) O(6) 3.239 2_456
H(62A) O(7) 3.522 2_456
H(62A) O(9) 3.271 2_456
H(62A) C(37) 3.532 2_456
H(62A) C(65) 3.412 2_456
H(62A) H(31) 3.232 2_456
H(62A) H(37) 3.304 2_456
H(62A) H(65B) 2.766 2_456
H(62A) H(72B) 3.016 2_456
H(62B) O(6) 3.498 2_456
H(62B) C(27) 3.337 1_455
H(62B) C(55) 3.383 .
H(62B) C(56) 3.163 .
H(62B) C(65) 3.303 2_456
H(62B) H(27) 2.925 1_455
H(62B) H(55) 3.199 .
H(62B) H(56) 2.831 .
H(62B) H(65A) 3.318 2_456
H(62B) H(65B) 2.722 2_456
H(62B) H(72B) 3.383 2_456
H(63A) Br(1) 3.276 .
H(63A) C(17) 3.378 4_565
H(63A) C(27) 3.205 1_455
H(63A) H(15) 3.564 4_565
H(63A) H(17) 2.730 4_565
H(63A) H(27) 2.391 1_455
H(63A) H(28) 3.309 1_455
H(63A) H(41) 3.231 4_565
H(63B) C(17) 3.326 4_565
H(63B) C(27) 3.538 1_455
H(63B) C(28) 3.372 1_455
H(63B) C(35) 3.376 2_456
H(63B) C(36) 2.863 2_456
H(63B) C(37) 2.929 2_456
H(63B) C(38) 3.528 2_456
H(63B) H(15) 3.313 4_565
H(63B) H(17) 2.411 4_565
H(63B) H(27) 3.063 1_455
H(63B) H(28) 2.735 1_455
H(63B) H(36) 3.039 2_456
H(63B) H(37) 3.120 2_456
H(63B) H(65B) 3.358 2_456
H(64A) O(8) 2.986 .
H(64A) C(15) 3.092 4_565
H(64A) C(66) 3.410 .
H(64A) C(67) 3.492 .
H(64A) H(15) 2.388 4_565
H(64A) H(17) 3.395 4_565
H(64A) H(41) 3.157 4_565
H(64A) H(66B) 2.789 .
H(64A) H(67A) 2.840 .
H(64B) C(30) 3.492 2_456
H(64B) C(31) 2.978 2_456
H(64B) C(33) 3.341 2_456
H(64B) C(38) 3.426 2_456
H(64B) C(66) 3.408 .
H(64B) H(15) 3.115 4_565
H(64B) H(30) 3.459 2_456
H(64B) H(31) 2.514 2_456
H(64B) H(44) 3.333 2_456
H(64B) H(66A) 3.229 .
H(64B) H(66B) 2.823 .
H(65A) C(19) 3.528 2_456
H(65A) C(20) 3.189 2_456
H(65A) C(24) 3.477 2_456
H(65A) C(25) 3.573 2_456
H(65A) C(27) 3.588 2_456
H(65A) C(28) 3.526 2_456
H(65A) C(29) 3.483 2_456
H(65A) C(56) 3.460 2_556
H(65A) H(19) 3.106 2_456
H(65A) H(20) 2.417 2_456
H(65A) H(56) 2.709 2_556
H(65A) H(57) 3.370 2_556
H(65A) H(62B) 3.318 2_556
H(65B) C(27) 3.355 2_456
H(65B) C(28) 2.946 2_456
H(65B) C(29) 3.256 2_456
H(65B) C(37) 3.500 .
H(65B) C(62) 3.119 2_556
H(65B) H(28) 3.027 2_456
H(65B) H(37) 2.724 .
H(65B) H(56) 3.582 2_556
H(65B) H(62A) 2.766 2_556
H(65B) H(62B) 2.722 2_556
H(65B) H(63B) 3.358 2_556
H(66A) C(20) 3.253 2_456
H(66A) C(23) 3.223 2_456
H(66A) C(24) 3.167 2_456
H(66A) C(29) 3.059 2_456
H(66A) C(30) 3.045 2_456
H(66A) C(31) 3.102 2_456
H(66A) C(32) 3.191 2_456
H(66A) C(44) 3.331 2_456
H(66A) H(20) 2.361 2_456
H(66A) H(30) 3.539 2_456
H(66A) H(44) 2.613 2_456
H(66A) H(64B) 3.229 .
H(66B) O(5) 2.400 .
H(66B) O(8) 3.316 .
H(66B) C(30) 3.324 2_456
H(66B) C(64) 2.847 .
H(66B) H(30) 3.378 2_456
H(66B) H(37) 2.773 .
H(66B) H(64A) 2.789 .
H(66B) H(64B) 2.823 .
H(67A) O(3) 3.575 4_565
H(67A) O(4) 3.426 4_565
H(67A) O(8) 3.206 .
H(67A) C(14) 3.590 4_565
H(67A) C(64) 3.561 .
H(67A) Li(1) 3.577 .
H(67A) H(6) 3.120 4_565
H(67A) H(14) 2.987 4_565
H(67A) H(15) 3.542 4_565
H(67A) H(64A) 2.840 .
H(67B) C(5) 3.025 4_565
H(67B) C(6) 3.103 4_565
H(67B) C(43) 3.188 2_456
H(67B) C(44) 3.334 2_456
H(67B) H(5) 2.670 4_565
H(67B) H(6) 2.848 4_565
H(67B) H(14) 2.973 4_565
H(67B) H(19) 3.480 2_456
H(67B) H(20) 3.209 2_456
H(67B) H(43) 2.537 2_456
H(67B) H(44) 2.827 2_456
H(68A) O(3) 3.178 4_565
H(68A) O(4) 2.558 4_565
H(68A) O(9) 3.088 .
H(68A) C(60) 3.168 4_565
H(68A) Li(1) 3.228 .
H(68A) H(5) 3.360 4_565
H(68A) H(6) 3.026 4_565
H(68A) H(71B) 2.901 .
H(68A) H(72B) 3.492 .
H(68B) C(5) 3.139 4_565
H(68B) C(6) 3.546 4_565
H(68B) H(5) 2.314 4_565
H(68B) H(6) 3.165 4_565
H(68B) H(10) 3.520 3_646
H(68B) H(19) 2.993 2_456
H(68B) H(57) 2.787 2_556
H(68B) H(71B) 3.402 .
H(69A) O(9) 3.054 .
H(69A) C(11) 3.522 .
H(69A) C(56) 3.487 4_565
H(69A) C(57) 3.477 4_565
H(69A) H(11) 2.603 .
H(69B) C(11) 3.332 .
H(69B) C(18) 3.016 4_665
H(69B) C(19) 3.478 4_665
H(69B) H(11) 2.494 .
H(69B) H(18) 2.671 4_665
H(69B) H(19) 3.488 4_665
H(69B) H(30) 3.301 .
H(70A) C(55) 3.138 4_565
H(70A) C(56) 2.974 4_565
H(70A) H(26) 3.431 4_665
H(70A) H(48) 3.086 3_646
H(70A) H(55) 3.154 4_565
H(70A) H(56) 2.870 4_565
H(70B) C(48) 3.075 3_646
H(70B) C(49) 3.584 3_646
H(70B) H(25) 3.597 4_665
H(70B) H(35) 3.245 2_556
H(70B) H(48) 2.272 3_646
H(70B) H(49) 3.298 3_646
H(71A) C(47) 3.403 3_646
H(71A) C(48) 3.074 3_646
H(71A) C(57) 3.482 2_556
H(71A) C(58) 3.040 2_556
H(71A) H(47) 3.184 3_646
H(71A) H(48) 2.575 3_646
H(71A) H(57) 3.450 2_556
H(71A) H(58) 2.688 2_556
H(71B) O(6) 3.492 .
H(71B) C(68) 3.413 .
H(71B) H(68A) 2.901 .
H(71B) H(68B) 3.402 .
H(72A) C(35) 3.243 2_556
H(72A) C(36) 3.400 2_556
H(72A) C(57) 3.583 2_556
H(72A) C(58) 3.379 2_556
H(72A) C(59) 3.531 2_556
H(72A) C(61) 3.599 2_556
H(72A) H(35) 2.854 2_556
H(72A) H(36) 3.148 2_556
H(72A) H(61A) 2.728 2_556
H(72B) O(6) 2.692 .
H(72B) O(9) 3.157 .
H(72B) C(56) 3.478 2_556
H(72B) C(57) 3.119 2_556
H(72B) C(58) 3.506 2_556
H(72B) C(61) 3.581 2_556
H(72B) C(62) 3.465 2_556
H(72B) C(68) 3.499 .
H(72B) H(57) 3.135 2_556
H(72B) H(61A) 2.930 2_556
H(72B) H(62A) 3.016 2_556
H(72B) H(62B) 3.383 2_556
H(72B) H(68A) 3.492 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
P(1) Ru(1) P(2) C(32) 39.11(16) . . .
P(1) Ru(1) P(2) C(33) 158.35(16) . . .
P(1) Ru(1) P(2) C(39) -81.83(18) . . .
P(2) Ru(1) P(1) C(1) 159.03(16) . . .
P(2) Ru(1) P(1) C(7) -79.98(19) . . .
P(2) Ru(1) P(1) C(13) 41.95(16) . . .
P(1) Ru(1) O(1) C(52) 74.3(3) . . .
O(1) Ru(1) P(1) C(1) -108.21(18) . . .
O(1) Ru(1) P(1) C(7) 12.8(2) . . .
O(1) Ru(1) P(1) C(13) 134.70(18) . . .
P(1) Ru(1) O(3) C(60) 163.0(3) . . .
O(3) Ru(1) P(1) C(1) 60.07(18) . . .
O(3) Ru(1) P(1) C(7) -178.9(2) . . .
O(3) Ru(1) P(1) C(13) -57.01(18) . . .
P(1) Ru(1) N(1) C(45) -62.9(2) . . .
N(1) Ru(1) P(1) C(1) -32.08(19) . . .
N(1) Ru(1) P(1) C(7) 88.9(2) . . .
N(1) Ru(1) P(1) C(13) -149.17(19) . . .
P(2) Ru(1) O(1) C(52) 163.6(3) . . .
O(1) Ru(1) P(2) C(32) -59.55(18) . . .
O(1) Ru(1) P(2) C(33) 59.69(19) . . .
O(1) Ru(1) P(2) C(39) 179.5(2) . . .
P(2) Ru(1) O(3) C(60) 73.4(3) . . .
O(3) Ru(1) P(2) C(32) 133.05(18) . . .
O(3) Ru(1) P(2) C(33) -107.71(19) . . .
O(3) Ru(1) P(2) C(39) 12.1(2) . . .
P(2) Ru(1) N(1) C(45) 32.8(7) . . .
N(1) Ru(1) P(2) C(32) -56.8(6) . . .
N(1) Ru(1) P(2) C(33) 62.4(6) . . .
N(1) Ru(1) P(2) C(39) -177.8(6) . . .
P(2) Ru(1) N(2) C(53) -69.8(2) . . .
N(2) Ru(1) P(2) C(32) -150.35(18) . . .
N(2) Ru(1) P(2) C(33) -31.11(19) . . .
N(2) Ru(1) P(2) C(39) 88.7(2) . . .
O(1) Ru(1) O(3) C(60) -59.5(5) . . .
O(3) Ru(1) O(1) C(52) -62.8(5) . . .
O(1) Ru(1) N(1) C(45) 35.5(2) . . .
N(1) Ru(1) O(1) C(52) -15.8(3) . . .
O(1) Ru(1) N(2) C(53) -162.7(2) . . .
N(2) Ru(1) O(1) C(52) -104.8(3) . . .
O(3) Ru(1) N(1) C(45) -157.0(2) . . .
N(1) Ru(1) O(3) C(60) -104.7(3) . . .
O(3) Ru(1) N(2) C(53) 29.1(2) . . .
N(2) Ru(1) O(3) C(60) -16.0(3) . . .
N(1) Ru(1) N(2) C(53) 121.3(2) . . .
N(2) Ru(1) N(1) C(45) 126.5(2) . . .
Ru(1) P(1) C(1) C(2) 133.0(4) . . .
Ru(1) P(1) C(1) C(6) -39.8(4) . . .
Ru(1) P(1) C(7) C(8) 175.2(3) . . .
Ru(1) P(1) C(7) C(12) -4.1(4) . . .
Ru(1) P(1) C(13) C(14) 94.8(3) . . .
Ru(1) P(1) C(13) C(22) -78.9(3) . . .
C(1) P(1) C(7) C(8) -59.7(4) . . .
C(1) P(1) C(7) C(12) 121.0(4) . . .
C(7) P(1) C(1) C(2) -0.6(4) . . .
C(7) P(1) C(1) C(6) -173.4(3) . . .
C(1) P(1) C(13) C(14) -25.9(4) . . .
C(1) P(1) C(13) C(22) 160.5(3) . . .
C(13) P(1) C(1) C(2) -105.0(4) . . .
C(13) P(1) C(1) C(6) 82.2(4) . . .
C(7) P(1) C(13) C(14) -130.8(3) . . .
C(7) P(1) C(13) C(22) 55.5(4) . . .
C(13) P(1) C(7) C(8) 47.9(4) . . .
C(13) P(1) C(7) C(12) -131.4(4) . . .
Ru(1) P(2) C(32) C(23) -78.7(3) . . .
Ru(1) P(2) C(32) C(31) 96.9(3) . . .
Ru(1) P(2) C(33) C(34) 116.3(4) . . .
Ru(1) P(2) C(33) C(38) -51.5(4) . . .
Ru(1) P(2) C(39) C(40) 0.4(4) . . .
Ru(1) P(2) C(39) C(44) 178.3(3) . . .
C(32) P(2) C(33) C(34) -120.3(4) . . .
C(32) P(2) C(33) C(38) 71.9(4) . . .
C(33) P(2) C(32) C(23) 160.9(3) . . .
C(33) P(2) C(32) C(31) -23.6(4) . . .
C(32) P(2) C(39) C(40) -127.0(4) . . .
C(32) P(2) C(39) C(44) 51.0(4) . . .
C(39) P(2) C(32) C(23) 55.4(4) . . .
C(39) P(2) C(32) C(31) -129.1(3) . . .
C(33) P(2) C(39) C(40) 123.5(4) . . .
C(33) P(2) C(39) C(44) -58.6(4) . . .
C(39) P(2) C(33) C(34) -16.6(4) . . .
C(39) P(2) C(33) C(38) 175.6(4) . . .
Ru(1) O(1) C(52) O(2) 174.8(3) . . .
Ru(1) O(1) C(52) C(45) -8.4(5) . . .
C(52) O(2) Li(1) O(8) -55.6(7) . . .
C(52) O(2) Li(1) O(9) 49.0(9) . . .
C(52) O(2) Li(1) O(4) 177.9(4) . . 4_565
Li(1) O(2) C(52) O(1) -18.6(8) . . .
Li(1) O(2) C(52) C(45) 164.9(5) . . .
Ru(1) O(3) C(60) O(4) -177.1(3) . . .
Ru(1) O(3) C(60) C(53) -1.5(5) . . .
C(60) O(4) Li(1) O(2) 49.3(14) . 4_564 4_564
C(60) O(4) Li(1) O(8) -61.5(12) . 4_564 4_564
C(60) O(4) Li(1) O(9) -178.0(8) . 4_564 4_564
Li(1) O(4) C(60) O(3) 100.0(11) 4_564 . .
Li(1) O(4) C(60) C(53) -75.3(12) 4_564 . .
C(61) O(5) C(64) C(63) -19.0(7) . . .
C(64) O(5) C(61) C(62) -5.3(7) . . .
C(65) O(6) C(68) C(67) -32.2(8) . . .
C(68) O(6) C(65) C(66) 38.6(7) . . .
C(69) O(7) C(72) C(71) 20.2(14) . . .
C(72) O(7) C(69) C(70) 6.2(19) . . .
Ru(1) N(1) C(45) C(46) 178.8(3) . . .
Ru(1) N(1) C(45) C(52) -49.0(3) . . .
Ru(1) N(2) C(53) C(54) -170.3(3) . . .
Ru(1) N(2) C(53) C(60) -37.9(4) . . .
P(1) C(1) C(2) C(3) -172.1(4) . . .
P(1) C(1) C(6) C(5) 173.3(3) . . .
C(2) C(1) C(6) C(5) 0.3(7) . . .
C(6) C(1) C(2) C(3) 0.5(7) . . .
C(1) C(2) C(3) C(4) 0.3(7) . . .
C(2) C(3) C(4) C(5) -1.9(7) . . .
C(3) C(4) C(5) C(6) 2.8(7) . . .
C(4) C(5) C(6) C(1) -1.9(7) . . .
P(1) C(7) C(8) C(9) 178.3(3) . . .
P(1) C(7) C(12) C(11) -179.0(3) . . .
C(8) C(7) C(12) C(11) 1.7(7) . . .
C(12) C(7) C(8) C(9) -2.3(7) . . .
C(7) C(8) C(9) C(10) 1.0(7) . . .
C(8) C(9) C(10) C(11) 1.0(7) . . .
C(9) C(10) C(11) C(12) -1.6(8) . . .
C(10) C(11) C(12) C(7) 0.3(7) . . .
P(1) C(13) C(14) C(15) -177.5(3) . . .
P(1) C(13) C(22) C(21) 177.0(3) . . .
P(1) C(13) C(22) C(23) -6.5(6) . . .
C(14) C(13) C(22) C(21) 3.3(6) . . .
C(14) C(13) C(22) C(23) 179.9(3) . . .
C(22) C(13) C(14) C(15) -3.8(7) . . .
C(13) C(14) C(15) C(16) 2.8(7) . . .
C(14) C(15) C(16) C(17) 180.0(4) . . .
C(14) C(15) C(16) C(21) -1.2(7) . . .
C(15) C(16) C(17) C(18) 178.5(5) . . .
C(15) C(16) C(21) C(20) -179.7(4) . . .
C(15) C(16) C(21) C(22) 0.7(7) . . .
C(17) C(16) C(21) C(20) -0.8(7) . . .
C(17) C(16) C(21) C(22) 179.5(4) . . .
C(21) C(16) C(17) C(18) -0.3(7) . . .
C(16) C(17) C(18) C(19) 0.9(8) . . .
C(17) C(18) C(19) C(20) -0.3(7) . . .
C(18) C(19) C(20) C(21) -0.9(7) . . .
C(19) C(20) C(21) C(16) 1.4(7) . . .
C(19) C(20) C(21) C(22) -178.9(4) . . .
C(16) C(21) C(22) C(13) -1.8(6) . . .
C(16) C(21) C(22) C(23) -178.5(4) . . .
C(20) C(21) C(22) C(13) 178.6(4) . . .
C(20) C(21) C(22) C(23) 1.9(6) . . .
C(13) C(22) C(23) C(24) -112.6(5) . . .
C(13) C(22) C(23) C(32) 69.1(6) . . .
C(21) C(22) C(23) C(24) 64.0(5) . . .
C(21) C(22) C(23) C(32) -114.3(5) . . .
C(22) C(23) C(24) C(25) 3.6(6) . . .
C(22) C(23) C(24) C(29) -178.1(4) . . .
C(22) C(23) C(32) P(2) -4.3(6) . . .
C(22) C(23) C(32) C(31) 180.0(3) . . .
C(24) C(23) C(32) P(2) 177.5(3) . . .
C(24) C(23) C(32) C(31) 1.8(6) . . .
C(32) C(23) C(24) C(25) -178.2(4) . . .
C(32) C(23) C(24) C(29) 0.1(5) . . .
C(23) C(24) C(25) C(26) -178.2(4) . . .
C(23) C(24) C(29) C(28) 177.8(4) . . .
C(23) C(24) C(29) C(30) -1.8(6) . . .
C(25) C(24) C(29) C(28) -3.8(6) . . .
C(25) C(24) C(29) C(30) 176.6(4) . . .
C(29) C(24) C(25) C(26) 3.5(6) . . .
C(24) C(25) C(26) C(27) -0.6(7) . . .
C(25) C(26) C(27) C(28) -2.0(7) . . .
C(26) C(27) C(28) C(29) 1.7(8) . . .
C(27) C(28) C(29) C(24) 1.3(7) . . .
C(27) C(28) C(29) C(30) -179.1(5) . . .
C(24) C(29) C(30) C(31) 1.6(7) . . .
C(28) C(29) C(30) C(31) -178.0(5) . . .
C(29) C(30) C(31) C(32) 0.3(7) . . .
C(30) C(31) C(32) P(2) -177.8(4) . . .
C(30) C(31) C(32) C(23) -2.0(7) . . .
P(2) C(33) C(34) C(35) -169.3(4) . . .
P(2) C(33) C(38) C(37) 171.4(4) . . .
C(34) C(33) C(38) C(37) 3.2(8) . . .
C(38) C(33) C(34) C(35) -1.4(7) . . .
C(33) C(34) C(35) C(36) -0.2(6) . . .
C(34) C(35) C(36) C(37) -0.1(7) . . .
C(35) C(36) C(37) C(38) 1.9(8) . . .
C(36) C(37) C(38) C(33) -3.6(8) . . .
P(2) C(39) C(40) C(41) 179.9(3) . . .
P(2) C(39) C(44) C(43) -178.5(3) . . .
C(40) C(39) C(44) C(43) -0.5(7) . . .
C(44) C(39) C(40) C(41) 1.9(7) . . .
C(39) C(40) C(41) C(42) -2.9(7) . . .
C(40) C(41) C(42) C(43) 2.4(7) . . .
C(41) C(42) C(43) C(44) -1.0(7) . . .
C(42) C(43) C(44) C(39) 0.1(6) . . .
N(1) C(45) C(46) C(47) -115.7(5) . . .
N(1) C(45) C(46) C(51) 64.3(6) . . .
N(1) C(45) C(52) O(1) 40.0(5) . . .
N(1) C(45) C(52) O(2) -143.2(4) . . .
C(46) C(45) C(52) O(1) 172.8(4) . . .
C(46) C(45) C(52) O(2) -10.4(6) . . .
C(52) C(45) C(46) C(47) 116.8(5) . . .
C(52) C(45) C(46) C(51) -63.2(6) . . .
C(45) C(46) C(47) C(48) 179.9(4) . . .
C(45) C(46) C(51) C(50) -179.7(4) . . .
C(47) C(46) C(51) C(50) 0.4(7) . . .
C(51) C(46) C(47) C(48) -0.1(6) . . .
C(46) C(47) C(48) C(49) 0.7(8) . . .
C(47) C(48) C(49) C(50) -1.3(8) . . .
C(48) C(49) C(50) C(51) 1.6(8) . . .
C(49) C(50) C(51) C(46) -1.1(7) . . .
N(2) C(53) C(54) C(55) 33.3(7) . . .
N(2) C(53) C(54) C(59) -148.8(4) . . .
N(2) C(53) C(60) O(3) 27.3(5) . . .
N(2) C(53) C(60) O(4) -157.1(4) . . .
C(54) C(53) C(60) O(3) 159.4(4) . . .
C(54) C(53) C(60) O(4) -25.0(6) . . .
C(60) C(53) C(54) C(55) -95.7(6) . . .
C(60) C(53) C(54) C(59) 82.1(5) . . .
C(53) C(54) C(55) C(56) 178.5(6) . . .
C(53) C(54) C(59) C(58) -178.5(4) . . .
C(55) C(54) C(59) C(58) -0.5(8) . . .
C(59) C(54) C(55) C(56) 0.6(9) . . .
C(54) C(55) C(56) C(57) 1.2(10) . . .
C(55) C(56) C(57) C(58) -3.1(10) . . .
C(56) C(57) C(58) C(59) 3.3(9) . . .
C(57) C(58) C(59) C(54) -1.4(8) . . .
O(5) C(61) C(62) C(63) 26.2(8) . . .
C(61) C(62) C(63) C(64) -36.0(8) . . .
C(62) C(63) C(64) O(5) 33.9(7) . . .
O(6) C(65) C(66) C(67) -28.0(7) . . .
C(65) C(66) C(67) C(68) 8.6(8) . . .
C(66) C(67) C(68) O(6) 14.0(8) . . .
O(7) C(69) C(70) C(71) -27(2) . . .
C(69) C(70) C(71) C(72) 36.0(16) . . .
C(70) C(71) C(72) O(7) -34.3(13) . . .
|
1502054.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502054.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502054
loop_
_publ_author_name
'Rihn, Sandra'
'Erdem, Mustafa'
'De Nicola, Antoinette'
'Retailleau, Pascal'
'Ziessel, Raymond'
_publ_section_title
;
Phenyliodine(III) bis(trifluoroacetate) (PIFA)-promoted synthesis of
Bodipy dimers displaying unusual redox properties.
;
_journal_issue 8
_journal_name_full 'Organic letters'
_journal_page_first 1916
_journal_page_last 1919
_journal_paper_doi 10.1021/ol200189y
_journal_volume 13
_journal_year 2011
_chemical_formula_moiety 'C28 H32 B2 F4 N4'
_chemical_formula_sum 'C28 H32 B2 F4 N4'
_chemical_formula_weight 522.20
_chemical_name_systematic
;
5,5,5',5'-tetrafluoro-1,1',3,3',7,7',9,9',10,10'
-decamethyl-5H,5'H-[2,2'-bidipyrrolo[1,2-c:2',1'-f]
[1,3,2]diazaborinine]-4,6'-diium-5,5'-diuide
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 102.161(7)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 12.5280(10)
_cell_length_b 12.7591(9)
_cell_length_c 16.6789(13)
_cell_measurement_reflns_used 2399
_cell_measurement_temperature 200(2)
_cell_measurement_theta_max 47.1
_cell_measurement_theta_min 6.8
_cell_volume 2606.2(4)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics 'PLATON (Spek, 2003)'
_computing_publication_material 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 200(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details
;
scan:
Number of images: 90
Slice: 20.0000 - 200.0000
Image width: 2.0000
Exp time: 720.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 270.0000
XTD: 127.4000
2theta: -0.2043
scan:
Number of images: 25
Slice: 58.0000 - 108.0000
Image width: 2.0000
Exp time: 720.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 54.0000
Phi: 0.0000
XTD: 127.4000
2theta: -0.2043
;
_diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method 'profile data from \w-scans'
_diffrn_orient_matrix_type FS_PROCESS
_diffrn_orient_matrix_UB_11 -0.020372
_diffrn_orient_matrix_UB_12 0.053309
_diffrn_orient_matrix_UB_13 -0.044551
_diffrn_orient_matrix_UB_21 0.076920
_diffrn_orient_matrix_UB_22 0.026286
_diffrn_orient_matrix_UB_23 0.011570
_diffrn_orient_matrix_UB_31 0.018319
_diffrn_orient_matrix_UB_32 -0.051088
_diffrn_orient_matrix_UB_33 -0.040534
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54187
_diffrn_reflns_av_R_equivalents 0.0698
_diffrn_reflns_av_sigmaI/netI 0.1266
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 5236
_diffrn_reflns_theta_full 47.20
_diffrn_reflns_theta_max 47.20
_diffrn_reflns_theta_min 6.81
_exptl_absorpt_coefficient_mu 0.814
_exptl_absorpt_correction_T_max 1.000
_exptl_absorpt_correction_T_min 0.553
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.331
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description platelet
_exptl_crystal_F_000 1096
_exptl_crystal_recrystallization_method 'recrystallized in dichloromethane'
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.03
_refine_diff_density_max 0.604
_refine_diff_density_min -0.283
_refine_diff_density_rms 0.064
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.096
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 353
_refine_ls_number_reflns 2173
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.096
_refine_ls_R_factor_all 0.1436
_refine_ls_R_factor_gt 0.0885
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2291
_refine_ls_wR_factor_ref 0.2741
_reflns_number_gt 1291
_reflns_number_total 2173
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200189y_si_002.cif
_cod_data_source_block EM004bis
_cod_original_cell_volume 2606.2(3)
_cod_original_sg_symbol_H-M 'P 21/c'
_cod_database_code 1502054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B1 B 0.6159(11) 0.9104(8) 0.2098(7) 0.067(3) Uani 1 1 d .
F1 F 0.7186(4) 0.9610(4) 0.2267(3) 0.0892(17) Uani 1 1 d .
F2 F 0.5921(4) 0.8766(3) 0.2824(2) 0.0777(16) Uani 1 1 d .
C1C C 0.7921(7) 0.7373(6) 0.2303(5) 0.070(3) Uani 1 1 d .
H1C1 H 0.8379 0.7984 0.2260 0.105 Uiso 1 1 calc R
H1C2 H 0.8341 0.6731 0.2274 0.105 Uiso 1 1 calc R
H1C3 H 0.7685 0.7395 0.2827 0.105 Uiso 1 1 calc R
C1A C 0.3632(7) 0.8401(6) -0.0152(6) 0.076(3) Uani 1 1 d .
H1A1 H 0.3833 0.8641 -0.0659 0.115 Uiso 1 1 calc R
H1A2 H 0.2954 0.8746 -0.0092 0.115 Uiso 1 1 calc R
H1A3 H 0.3524 0.7640 -0.0176 0.115 Uiso 1 1 calc R
C1B C 0.5760(7) 1.1338(6) 0.2671(6) 0.082(3) Uani 1 1 d .
H1B1 H 0.5754 1.0884 0.3144 0.123 Uiso 1 1 calc R
H1B2 H 0.5454 1.2024 0.2763 0.123 Uiso 1 1 calc R
H1B3 H 0.6512 1.1426 0.2601 0.123 Uiso 1 1 calc R
N1 N 0.5296(7) 0.9875(6) 0.1669(5) 0.058(2) Uani 1 1 d .
N2 N 0.6198(7) 0.8183(6) 0.1517(5) 0.0557(19) Uani 1 1 d .
C1 C 0.4488(9) 0.9633(7) 0.0967(7) 0.060(3) Uani 1 1 d .
C2 C 0.3769(9) 1.0504(9) 0.0795(7) 0.068(3) Uani 1 1 d .
C3 C 0.4171(9) 1.1239(7) 0.1384(7) 0.064(3) Uani 1 1 d .
H3 H 0.3867 1.1915 0.1420 0.076 Uiso 1 1 calc R
C4 C 0.5087(9) 1.0851(8) 0.1916(6) 0.059(2) Uani 1 1 d .
C5 C 0.6942(8) 0.7386(8) 0.1612(6) 0.059(2) Uani 1 1 d .
C6 C 0.6635(8) 0.6659(7) 0.0988(6) 0.058(2) Uani 1 1 d .
C7 C 0.5632(9) 0.6974(7) 0.0480(6) 0.061(2) Uani 1 1 d .
C8 C 0.5377(9) 0.7954(7) 0.0818(6) 0.057(2) Uani 1 1 d .
C9 C 0.4529(8) 0.8671(8) 0.0568(6) 0.061(3) Uani 1 1 d .
C10 C 0.2778(8) 1.0635(7) 0.0120(6) 0.083(3) Uani 1 1 d .
H10A H 0.2456 1.1327 0.0163 0.125 Uiso 1 1 calc R
H10B H 0.2243 1.0090 0.0166 0.125 Uiso 1 1 calc R
H10C H 0.2989 1.0573 -0.0412 0.125 Uiso 1 1 calc R
C11 C 0.5033(7) 0.6409(6) -0.0265(5) 0.070(3) Uani 1 1 d .
H11A H 0.5443 0.5780 -0.0354 0.105 Uiso 1 1 calc R
H11B H 0.4957 0.6870 -0.0744 0.105 Uiso 1 1 calc R
H11C H 0.4308 0.6205 -0.0186 0.105 Uiso 1 1 calc R
B1' B 0.8471(10) 0.3121(9) 0.1598(8) 0.069(3) Uani 1 1 d .
F1' F 0.7706(5) 0.2547(4) 0.1920(3) 0.1064(19) Uani 1 1 d .
F2' F 0.9253(5) 0.3416(4) 0.2338(3) 0.107(2) Uani 1 1 d .
N1' N 0.9041(5) 0.2454(6) 0.1083(4) 0.064(2) Uani 1 1 d .
N2' N 0.7993(6) 0.4103(6) 0.1193(4) 0.065(2) Uani 1 1 d .
C4' C 0.9525(7) 0.1493(7) 0.1251(6) 0.060(2) Uani 1 1 d .
C3' C 0.9986(7) 0.1219(7) 0.0605(6) 0.070(3) Uani 1 1 d .
H3' H 1.0368 0.0585 0.0565 0.084 Uiso 1 1 calc R
C2' C 0.9812(7) 0.1994(8) 0.0031(5) 0.066(3) Uani 1 1 d .
C1' C 0.9202(6) 0.2785(7) 0.0314(5) 0.049(2) Uani 1 1 d .
C7' C 0.7727(6) 0.5428(7) 0.0251(5) 0.057(2) Uani 1 1 d .
C9' C 0.8794(7) 0.3756(7) 0.0002(5) 0.071(3) Uani 1 1 d .
C1A' C 0.9001(9) 0.4099(7) -0.0802(5) 0.117(4) Uani 1 1 d .
H1A4 H 0.9034 0.3484 -0.1148 0.175 Uiso 1 1 calc R
H1A5 H 0.9697 0.4477 -0.0717 0.175 Uiso 1 1 calc R
H1A6 H 0.8409 0.4562 -0.1072 0.175 Uiso 1 1 calc R
C10' C 1.0181(7) 0.1965(7) -0.0765(4) 0.082(3) Uani 1 1 d .
H10D H 0.9544 0.2000 -0.1220 0.123 Uiso 1 1 calc R
H10E H 1.0580 0.1312 -0.0802 0.123 Uiso 1 1 calc R
H10F H 1.0661 0.2564 -0.0794 0.123 Uiso 1 1 calc R
C1B' C 0.9472(7) 0.0882(6) 0.2009(5) 0.077(3) Uani 1 1 d .
H1B4 H 0.9677 0.1337 0.2491 0.115 Uiso 1 1 calc R
H1B5 H 0.9977 0.0288 0.2061 0.115 Uiso 1 1 calc R
H1B6 H 0.8727 0.0622 0.1972 0.115 Uiso 1 1 calc R
C8' C 0.8196(6) 0.4414(7) 0.0423(4) 0.051(2) Uani 1 1 d .
C6' C 0.7225(7) 0.5681(7) 0.0903(5) 0.060(2) Uani 1 1 d .
C5' C 0.7391(7) 0.4835(7) 0.1458(5) 0.061(2) Uani 1 1 d .
C11' C 0.7780(7) 0.6116(6) -0.0469(5) 0.074(3) Uani 1 1 d .
H11D H 0.7374 0.5787 -0.0973 0.112 Uiso 1 1 calc R
H11E H 0.8544 0.6210 -0.0509 0.112 Uiso 1 1 calc R
H11F H 0.7457 0.6800 -0.0397 0.112 Uiso 1 1 calc R
C1C' C 0.6999(8) 0.4736(7) 0.2235(4) 0.088(3) Uani 1 1 d .
H1C4 H 0.6463 0.4167 0.2184 0.132 Uiso 1 1 calc R
H1C5 H 0.6656 0.5396 0.2348 0.132 Uiso 1 1 calc R
H1C6 H 0.7617 0.4581 0.2686 0.132 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.080(10) 0.055(8) 0.080(9) 0.007(7) 0.047(8) 0.004(8)
F1 0.071(4) 0.071(3) 0.128(4) -0.004(3) 0.025(3) 0.000(3)
F2 0.098(4) 0.073(3) 0.062(3) 0.008(3) 0.019(3) 0.011(3)
C1C 0.067(7) 0.070(6) 0.072(6) -0.003(5) 0.013(6) 0.013(5)
C1A 0.077(7) 0.067(6) 0.083(7) -0.006(6) 0.010(6) 0.018(6)
C1B 0.092(8) 0.065(6) 0.095(8) -0.009(6) 0.034(7) 0.001(6)
N1 0.075(6) 0.040(5) 0.061(6) 0.001(5) 0.020(5) 0.008(5)
N2 0.056(5) 0.056(5) 0.056(5) -0.001(5) 0.015(5) 0.000(5)
C1 0.083(8) 0.044(7) 0.055(7) 0.005(6) 0.023(7) 0.005(7)
C2 0.071(8) 0.060(7) 0.075(8) 0.004(7) 0.022(7) -0.009(7)
C3 0.058(7) 0.056(6) 0.077(7) 0.012(7) 0.014(6) 0.008(6)
C4 0.051(7) 0.066(8) 0.062(7) -0.002(7) 0.014(6) -0.006(6)
C5 0.064(8) 0.061(7) 0.055(7) 0.003(6) 0.020(6) -0.002(7)
C6 0.060(7) 0.056(6) 0.062(7) 0.000(6) 0.021(6) 0.007(6)
C7 0.056(7) 0.056(7) 0.075(7) 0.006(6) 0.025(7) 0.007(6)
C8 0.064(7) 0.050(7) 0.057(7) 0.005(6) 0.016(7) 0.002(6)
C9 0.069(7) 0.064(7) 0.052(7) 0.005(6) 0.016(6) -0.009(6)
C10 0.077(7) 0.069(6) 0.100(7) 0.012(6) 0.009(7) 0.011(6)
C11 0.071(7) 0.070(6) 0.064(6) -0.010(5) 0.002(6) -0.002(5)
B1' 0.068(8) 0.058(8) 0.074(9) 0.012(8) 0.002(8) -0.013(7)
F1' 0.127(5) 0.080(4) 0.128(4) 0.014(3) 0.061(4) 0.011(3)
F2' 0.124(5) 0.100(4) 0.086(4) -0.014(3) 0.000(4) 0.021(4)
N1' 0.074(6) 0.059(5) 0.059(5) -0.014(5) 0.014(4) -0.003(5)
N2' 0.083(6) 0.062(5) 0.054(5) 0.005(4) 0.020(4) 0.017(5)
C4' 0.054(6) 0.041(6) 0.081(7) -0.006(6) 0.004(6) -0.003(5)
C3' 0.084(7) 0.070(7) 0.066(6) -0.010(6) 0.037(6) 0.000(6)
C2' 0.076(7) 0.069(7) 0.054(6) -0.008(6) 0.015(6) 0.008(6)
C1' 0.056(6) 0.055(6) 0.032(5) -0.006(5) 0.000(5) 0.016(5)
C7' 0.054(6) 0.057(6) 0.065(6) 0.006(6) 0.021(5) 0.004(5)
C9' 0.091(8) 0.064(7) 0.055(6) -0.001(6) 0.007(6) 0.008(6)
C1A' 0.190(12) 0.087(8) 0.101(7) 0.025(6) 0.091(8) 0.072(8)
C10' 0.093(7) 0.096(7) 0.055(6) -0.005(5) 0.014(6) 0.025(6)
C1B' 0.092(7) 0.067(6) 0.079(6) 0.003(5) 0.035(6) -0.020(5)
C8' 0.058(6) 0.060(6) 0.037(5) -0.010(5) 0.012(5) 0.009(5)
C6' 0.065(6) 0.060(6) 0.053(6) -0.004(5) 0.011(5) 0.011(5)
C5' 0.063(6) 0.053(6) 0.061(6) -0.002(6) 0.002(5) 0.010(5)
C11' 0.078(7) 0.077(6) 0.075(6) 0.012(6) 0.031(5) 0.011(5)
C1C' 0.127(9) 0.089(7) 0.060(6) -0.001(5) 0.045(6) 0.016(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
F2 B1 F1 108.9(10)
F2 B1 N1 110.6(8)
F1 B1 N1 108.9(8)
F2 B1 N2 111.0(8)
F1 B1 N2 109.2(8)
N1 B1 N2 108.2(9)
C5 C1C H1C1 109.5
C5 C1C H1C2 109.5
H1C1 C1C H1C2 109.5
C5 C1C H1C3 109.5
H1C1 C1C H1C3 109.5
H1C2 C1C H1C3 109.5
C9 C1A H1A1 109.5
C9 C1A H1A2 109.5
H1A1 C1A H1A2 109.5
C9 C1A H1A3 109.5
H1A1 C1A H1A3 109.5
H1A2 C1A H1A3 109.5
C4 C1B H1B1 109.5
C4 C1B H1B2 109.5
H1B1 C1B H1B2 109.5
C4 C1B H1B3 109.5
H1B1 C1B H1B3 109.5
H1B2 C1B H1B3 109.5
C4 N1 C1 107.6(8)
C4 N1 B1 127.9(11)
C1 N1 B1 124.2(8)
C5 N2 C8 107.6(8)
C5 N2 B1 127.6(10)
C8 N2 B1 124.5(9)
C9 C1 N1 119.5(10)
C9 C1 C2 132.4(13)
N1 C1 C2 108.0(9)
C3 C2 C1 105.6(9)
C3 C2 C10 125.6(10)
C1 C2 C10 128.8(11)
C2 C3 C4 110.1(9)
C2 C3 H3 125.0
C4 C3 H3 125.0
N1 C4 C3 108.7(9)
N1 C4 C1B 121.9(11)
C3 C4 C1B 129.4(10)
N2 C5 C6 109.6(8)
N2 C5 C1C 121.8(9)
C6 C5 C1C 128.6(10)
C5 C6 C7 109.3(8)
C5 C6 C6' 125.0(10)
C7 C6 C6' 125.6(9)
C6 C7 C8 104.7(9)
C6 C7 C11 125.9(8)
C8 C7 C11 129.3(10)
C9 C8 N2 119.1(9)
C9 C8 C7 132.1(11)
N2 C8 C7 108.7(9)
C8 C9 C1 122.2(10)
C8 C9 C1A 118.9(9)
C1 C9 C1A 118.9(10)
C2 C10 H10A 109.5
C2 C10 H10B 109.5
H10A C10 H10B 109.5
C2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C7 C11 H11A 109.5
C7 C11 H11B 109.5
H11A C11 H11B 109.5
C7 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
F1' B1' F2' 101.8(9)
F1' B1' N2' 111.9(9)
F2' B1' N2' 107.6(8)
F1' B1' N1' 111.8(8)
F2' B1' N1' 108.4(8)
N2' B1' N1' 114.5(9)
C4' N1' C1' 108.2(7)
C4' N1' B1' 129.6(8)
C1' N1' B1' 122.2(8)
C5' N2' C8' 109.0(7)
C5' N2' B1' 129.8(8)
C8' N2' B1' 121.1(8)
C3' C4' N1' 108.0(8)
C3' C4' C1B' 129.2(9)
N1' C4' C1B' 122.7(8)
C2' C3' C4' 109.7(8)
C2' C3' H3' 125.2
C4' C3' H3' 125.2
C3' C2' C1' 107.6(7)
C3' C2' C10' 125.0(8)
C1' C2' C10' 127.4(9)
C9' C1' N1' 119.6(8)
C9' C1' C2' 133.8(8)
N1' C1' C2' 106.5(8)
C6' C7' C8' 106.6(7)
C6' C7' C11' 126.0(8)
C8' C7' C11' 127.3(7)
C1' C9' C8' 122.3(8)
C1' C9' C1A' 118.5(8)
C8' C9' C1A' 119.2(8)
C9' C1A' H1A4 109.5
C9' C1A' H1A5 109.5
H1A4 C1A' H1A5 109.5
C9' C1A' H1A6 109.5
H1A4 C1A' H1A6 109.5
H1A5 C1A' H1A6 109.5
C2' C10' H10D 109.5
C2' C10' H10E 109.5
H10D C10' H10E 109.5
C2' C10' H10F 109.5
H10D C10' H10F 109.5
H10E C10' H10F 109.5
C4' C1B' H1B4 109.5
C4' C1B' H1B5 109.5
H1B4 C1B' H1B5 109.5
C4' C1B' H1B6 109.5
H1B4 C1B' H1B6 109.5
H1B5 C1B' H1B6 109.5
C9' C8' N2' 120.0(8)
C9' C8' C7' 133.0(8)
N2' C8' C7' 107.0(7)
C7' C6' C5' 107.7(7)
C7' C6' C6 125.8(8)
C5' C6' C6 126.5(8)
N2' C5' C6' 109.5(8)
N2' C5' C1C' 123.0(8)
C6' C5' C1C' 127.4(8)
C7' C11' H11D 109.5
C7' C11' H11E 109.5
H11D C11' H11E 109.5
C7' C11' H11F 109.5
H11D C11' H11F 109.5
H11E C11' H11F 109.5
C5' C1C' H1C4 109.5
C5' C1C' H1C5 109.5
H1C4 C1C' H1C5 109.5
C5' C1C' H1C6 109.5
H1C4 C1C' H1C6 109.5
H1C5 C1C' H1C6 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F2 1.377(10)
B1 F1 1.414(11)
B1 N1 1.524(12)
B1 N2 1.530(12)
C1C C5 1.496(11)
C1C H1C1 0.9800
C1C H1C2 0.9800
C1C H1C3 0.9800
C1A C9 1.502(10)
C1A H1A1 0.9800
C1A H1A2 0.9800
C1A H1A3 0.9800
C1B C4 1.494(11)
C1B H1B1 0.9800
C1B H1B2 0.9800
C1B H1B3 0.9800
N1 C4 1.356(10)
N1 C1 1.412(10)
N2 C5 1.366(9)
N2 C8 1.412(10)
C1 C9 1.402(11)
C1 C2 1.421(12)
C2 C3 1.374(10)
C2 C10 1.500(11)
C3 C4 1.386(10)
C3 H3 0.9500
C5 C6 1.387(10)
C6 C7 1.417(10)
C6 C6' 1.472(11)
C7 C8 1.436(11)
C7 C11 1.495(10)
C8 C9 1.397(11)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
B1' F1' 1.400(11)
B1' F2' 1.454(11)
B1' N2' 1.488(12)
B1' N1' 1.493(12)
N1' C4' 1.371(8)
N1' C1' 1.405(8)
N2' C5' 1.333(9)
N2' C8' 1.418(8)
C4' C3' 1.369(10)
C4' C1B' 1.500(10)
C3' C2' 1.361(10)
C3' H3' 0.9500
C2' C1' 1.406(10)
C2' C10' 1.495(10)
C1' C9' 1.399(10)
C7' C6' 1.404(10)
C7' C8' 1.424(10)
C7' C11' 1.501(9)
C9' C8' 1.408(10)
C9' C1A' 1.484(10)
C1A' H1A4 0.9800
C1A' H1A5 0.9800
C1A' H1A6 0.9800
C10' H10D 0.9800
C10' H10E 0.9800
C10' H10F 0.9800
C1B' H1B4 0.9800
C1B' H1B5 0.9800
C1B' H1B6 0.9800
C6' C5' 1.409(10)
C5' C1C' 1.485(10)
C11' H11D 0.9800
C11' H11E 0.9800
C11' H11F 0.9800
C1C' H1C4 0.9800
C1C' H1C5 0.9800
C1C' H1C6 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
F2 B1 N1 C4 67.1(12)
F1 B1 N1 C4 -52.6(11)
N2 B1 N1 C4 -171.1(7)
F2 B1 N1 C1 -106.0(9)
F1 B1 N1 C1 134.3(8)
N2 B1 N1 C1 15.8(10)
F2 B1 N2 C5 -67.3(12)
F1 B1 N2 C5 52.8(11)
N1 B1 N2 C5 171.2(7)
F2 B1 N2 C8 105.3(10)
F1 B1 N2 C8 -134.6(8)
N1 B1 N2 C8 -16.2(11)
C4 N1 C1 C9 178.2(7)
B1 N1 C1 C9 -7.5(11)
C4 N1 C1 C2 -0.2(8)
B1 N1 C1 C2 174.1(7)
C9 C1 C2 C3 -177.2(8)
N1 C1 C2 C3 0.9(8)
C9 C1 C2 C10 2.3(14)
N1 C1 C2 C10 -179.6(7)
C1 C2 C3 C4 -1.2(9)
C10 C2 C3 C4 179.2(7)
C1 N1 C4 C3 -0.6(8)
B1 N1 C4 C3 -174.6(7)
C1 N1 C4 C1B 177.2(6)
B1 N1 C4 C1B 3.2(12)
C2 C3 C4 N1 1.2(9)
C2 C3 C4 C1B -176.3(7)
C8 N2 C5 C6 1.0(8)
B1 N2 C5 C6 174.7(7)
C8 N2 C5 C1C -179.5(6)
B1 N2 C5 C1C -5.8(11)
N2 C5 C6 C7 -2.1(9)
C1C C5 C6 C7 178.5(7)
N2 C5 C6 C6' -178.3(7)
C1C C5 C6 C6' 2.3(12)
C5 C6 C7 C8 2.2(8)
C6' C6 C7 C8 178.4(7)
C5 C6 C7 C11 179.3(7)
C6' C6 C7 C11 -4.5(12)
C5 N2 C8 C9 -177.9(6)
B1 N2 C8 C9 8.2(11)
C5 N2 C8 C7 0.4(8)
B1 N2 C8 C7 -173.5(7)
C6 C7 C8 C9 176.5(8)
C11 C7 C8 C9 -0.5(14)
C6 C7 C8 N2 -1.6(8)
C11 C7 C8 N2 -178.6(7)
N2 C8 C9 C1 2.8(11)
C7 C8 C9 C1 -175.0(7)
N2 C8 C9 C1A -177.3(6)
C7 C8 C9 C1A 4.8(13)
N1 C1 C9 C8 -3.2(11)
C2 C1 C9 C8 174.8(7)
N1 C1 C9 C1A 177.0(6)
C2 C1 C9 C1A -5.1(12)
F1' B1' N1' C4' -48.5(14)
F2' B1' N1' C4' 62.9(11)
N2' B1' N1' C4' -177.0(7)
F1' B1' N1' C1' 134.6(8)
F2' B1' N1' C1' -114.1(8)
N2' B1' N1' C1' 6.1(13)
F1' B1' N2' C5' 47.7(14)
F2' B1' N2' C5' -63.2(12)
N1' B1' N2' C5' 176.1(8)
F1' B1' N2' C8' -135.8(8)
F2' B1' N2' C8' 113.2(9)
N1' B1' N2' C8' -7.4(13)
C1' N1' C4' C3' 0.2(9)
B1' N1' C4' C3' -177.1(8)
C1' N1' C4' C1B' -177.3(7)
B1' N1' C4' C1B' 5.4(13)
N1' C4' C3' C2' 0.5(10)
C1B' C4' C3' C2' 177.8(7)
C4' C3' C2' C1' -1.0(10)
C4' C3' C2' C10' -179.0(8)
C4' N1' C1' C9' -179.4(7)
B1' N1' C1' C9' -1.8(12)
C4' N1' C1' C2' -0.7(8)
B1' N1' C1' C2' 176.8(8)
C3' C2' C1' C9' 179.4(9)
C10' C2' C1' C9' -2.7(15)
C3' C2' C1' N1' 1.0(9)
C10' C2' C1' N1' 179.0(8)
N1' C1' C9' C8' -1.6(12)
C2' C1' C9' C8' -179.8(8)
N1' C1' C9' C1A' 178.4(7)
C2' C1' C9' C1A' 0.2(15)
C1' C9' C8' N2' 0.2(12)
C1A' C9' C8' N2' -179.8(7)
C1' C9' C8' C7' 178.1(8)
C1A' C9' C8' C7' -1.9(14)
C5' N2' C8' C9' -178.3(7)
B1' N2' C8' C9' 4.6(12)
C5' N2' C8' C7' 3.3(9)
B1' N2' C8' C7' -173.8(8)
C6' C7' C8' C9' 179.9(8)
C11' C7' C8' C9' -1.7(15)
C6' C7' C8' N2' -2.1(9)
C11' C7' C8' N2' 176.3(7)
C8' C7' C6' C5' 0.1(9)
C11' C7' C6' C5' -178.2(7)
C8' C7' C6' C6 180.0(8)
C11' C7' C6' C6 1.6(14)
C5 C6 C6' C7' -117.0(9)
C7 C6 C6' C7' 67.4(12)
C5 C6 C6' C5' 62.8(12)
C7 C6 C6' C5' -112.8(10)
C8' N2' C5' C6' -3.3(9)
B1' N2' C5' C6' 173.5(9)
C8' N2' C5' C1C' 177.8(7)
B1' N2' C5' C1C' -5.4(14)
C7' C6' C5' N2' 2.0(9)
C6 C6' C5' N2' -177.8(8)
C7' C6' C5' C1C' -179.2(8)
C6 C6' C5' C1C' 1.0(14)
|
1502055.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502055.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502055
loop_
_publ_author_name
'Brown, Michael J.'
'Clarkson, Guy J.'
'Inglis, Graham G.'
'Shipman, Michael'
_publ_section_title
;
Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using
transition metal catalysis.
;
_journal_issue 7
_journal_name_full 'Organic letters'
_journal_page_first 1686
_journal_page_last 1689
_journal_paper_doi 10.1021/ol200193n
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C15 H18 N2 O4'
_chemical_formula_weight 290.31
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 102.439(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 11.5971(3)
_cell_length_b 17.5177(5)
_cell_length_c 7.3754(2)
_cell_measurement_reflns_used 6985
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 29.11
_cell_measurement_theta_min 2.93
_cell_volume 1463.17(7)
_computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)'
_computing_publication_material 'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type 'Oxford Diffraction Gemini R'
_diffrn_measurement_method '\f & \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0288
_diffrn_reflns_av_sigmaI/netI 0.0307
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_number 12834
_diffrn_reflns_theta_full 26.50
_diffrn_reflns_theta_max 29.15
_diffrn_reflns_theta_min 2.94
_diffrn_standards_decay_% nil
_exptl_absorpt_coefficient_mu 0.096
_exptl_absorpt_correction_T_max 1.00
_exptl_absorpt_correction_T_min 0.87
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.318
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 616
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_refine_diff_density_max 0.495
_refine_diff_density_min -0.322
_refine_diff_density_rms 0.045
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.094
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 192
_refine_ls_number_reflns 3521
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.094
_refine_ls_R_factor_all 0.0531
_refine_ls_R_factor_gt 0.0405
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.1691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1008
_refine_ls_wR_factor_ref 0.1047
_reflns_number_gt 2804
_reflns_number_total 3521
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200193n_si_002.cif
_cod_data_source_block mb9
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.82875(11) 0.30290(7) 0.56038(17) 0.0200(3) Uani 1 1 d .
H1A H 0.8467 0.2535 0.5209 0.024 Uiso 1 1 calc R
C2 C 0.90832(11) 0.36177(8) 0.56081(17) 0.0225(3) Uani 1 1 d .
H2A H 0.9802 0.3525 0.5225 0.027 Uiso 1 1 calc R
C3 C 0.88316(11) 0.43428(7) 0.61726(17) 0.0222(3) Uani 1 1 d .
H3A H 0.9379 0.4747 0.6184 0.027 Uiso 1 1 calc R
C4 C 0.77777(11) 0.44741(7) 0.67193(18) 0.0220(3) Uani 1 1 d .
H4A H 0.7600 0.4971 0.7096 0.026 Uiso 1 1 calc R
C5 C 0.69824(11) 0.38835(7) 0.67191(17) 0.0202(3) Uani 1 1 d .
H5A H 0.6263 0.3980 0.7097 0.024 Uiso 1 1 calc R
C6 C 0.72238(10) 0.31459(7) 0.61699(15) 0.0164(2) Uani 1 1 d .
C7 C 0.64376(11) 0.24907(7) 0.61686(15) 0.0164(2) Uani 1 1 d .
H7A H 0.6721 0.2009 0.5866 0.020 Uiso 1 1 calc R
C8 C 0.53682(10) 0.25021(6) 0.65478(15) 0.0155(2) Uani 1 1 d .
C9 C 0.45022(10) 0.30657(7) 0.70505(16) 0.0158(2) Uani 1 1 d .
H9A H 0.4813 0.3356 0.8204 0.019 Uiso 1 1 calc R
H9B H 0.4136 0.3410 0.6022 0.019 Uiso 1 1 calc R
N10 N 0.37491(9) 0.23941(5) 0.73062(14) 0.0163(2) Uani 1 1 d .
N11 N 0.45577(9) 0.18906(6) 0.66290(13) 0.0163(2) Uani 1 1 d .
O12 O 0.41825(7) 0.08445(5) 0.82934(11) 0.0200(2) Uani 1 1 d .
C12 C 0.47768(10) 0.11632(7) 0.73713(15) 0.0160(2) Uani 1 1 d .
O13 O 0.56989(7) 0.08690(4) 0.67925(11) 0.0190(2) Uani 1 1 d .
C14 C 0.59707(11) 0.00764(7) 0.73399(17) 0.0206(3) Uani 1 1 d .
H14A H 0.5315 -0.0262 0.6740 0.025 Uiso 1 1 calc R
H14B H 0.6085 0.0022 0.8703 0.025 Uiso 1 1 calc R
C15 C 0.70821(12) -0.01329(8) 0.67277(19) 0.0269(3) Uani 1 1 d .
H15A H 0.7304 -0.0658 0.7106 0.040 Uiso 1 1 calc R
H15B H 0.7718 0.0215 0.7304 0.040 Uiso 1 1 calc R
H15C H 0.6950 -0.0092 0.5373 0.040 Uiso 1 1 calc R
O16 O 0.19663(8) 0.29591(5) 0.62036(12) 0.0263(2) Uani 1 1 d .
C16 C 0.25719(11) 0.23944(7) 0.63245(16) 0.0190(3) Uani 1 1 d .
O17 O 0.22403(8) 0.17009(5) 0.56987(12) 0.0245(2) Uani 1 1 d .
C18 C 0.09973(12) 0.15999(8) 0.4831(2) 0.0290(3) Uani 1 1 d .
H18A H 0.0921 0.1234 0.3788 0.035 Uiso 1 1 calc R
H18B H 0.0659 0.2094 0.4323 0.035 Uiso 1 1 calc R
C19 C 0.03377(14) 0.13126(11) 0.6187(3) 0.0464(4) Uani 1 1 d .
H19A H -0.0474 0.1193 0.5550 0.070 Uiso 1 1 calc R
H19B H 0.0327 0.1703 0.7134 0.070 Uiso 1 1 calc R
H19C H 0.0721 0.0850 0.6779 0.070 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0186(6) 0.0215(6) 0.0201(6) -0.0015(5) 0.0045(5) 0.0031(5)
C2 0.0174(6) 0.0280(7) 0.0232(6) -0.0006(5) 0.0071(5) 0.0010(5)
C3 0.0186(6) 0.0236(7) 0.0246(6) 0.0013(5) 0.0047(5) -0.0042(5)
C4 0.0223(7) 0.0170(6) 0.0272(6) -0.0015(5) 0.0067(5) 0.0004(5)
C5 0.0173(6) 0.0201(6) 0.0247(6) 0.0003(5) 0.0079(5) 0.0018(5)
C6 0.0169(6) 0.0183(6) 0.0137(5) 0.0020(5) 0.0025(4) 0.0013(4)
C7 0.0181(6) 0.0159(6) 0.0152(5) -0.0007(5) 0.0034(4) 0.0018(4)
C8 0.0195(6) 0.0137(6) 0.0127(5) 0.0001(4) 0.0023(4) 0.0003(4)
C9 0.0175(6) 0.0143(6) 0.0162(5) 0.0007(4) 0.0053(4) -0.0007(4)
N10 0.0168(5) 0.0146(5) 0.0185(5) -0.0013(4) 0.0058(4) 0.0007(4)
N11 0.0166(5) 0.0155(5) 0.0177(5) -0.0009(4) 0.0059(4) 0.0010(4)
O12 0.0233(5) 0.0190(4) 0.0192(4) 0.0010(3) 0.0075(3) -0.0032(3)
C12 0.0188(6) 0.0148(6) 0.0138(5) -0.0027(4) 0.0022(4) -0.0015(4)
O13 0.0227(5) 0.0136(4) 0.0220(4) 0.0004(3) 0.0080(3) 0.0015(3)
C14 0.0266(7) 0.0125(6) 0.0223(6) 0.0013(5) 0.0044(5) 0.0019(5)
C15 0.0302(7) 0.0205(6) 0.0304(7) 0.0009(6) 0.0076(5) 0.0058(5)
O16 0.0199(5) 0.0287(5) 0.0307(5) -0.0003(4) 0.0062(4) 0.0060(4)
C16 0.0194(6) 0.0234(6) 0.0154(5) 0.0008(5) 0.0064(5) 0.0005(5)
O17 0.0185(5) 0.0251(5) 0.0277(5) -0.0040(4) 0.0004(4) -0.0031(3)
C18 0.0178(7) 0.0357(8) 0.0312(7) -0.0032(6) 0.0000(5) -0.0059(5)
C19 0.0272(8) 0.0573(11) 0.0555(10) 0.0230(9) 0.0105(7) -0.0017(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 121.37(12)
C2 C1 H1A 119.3
C6 C1 H1A 119.3
C1 C2 C3 119.99(12)
C1 C2 H2A 120.0
C3 C2 H2A 120.0
C4 C3 C2 119.66(12)
C4 C3 H3A 120.2
C2 C3 H3A 120.2
C5 C4 C3 120.30(12)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
C4 C5 C6 120.95(11)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C1 C6 C5 117.72(11)
C1 C6 C7 118.24(11)
C5 C6 C7 124.03(11)
C8 C7 C6 126.63(11)
C8 C7 H7A 116.7
C6 C7 H7A 116.7
C7 C8 N11 130.31(11)
C7 C8 C9 139.60(11)
N11 C8 C9 90.09(9)
N10 C9 C8 87.37(8)
N10 C9 H9A 114.1
C8 C9 H9A 114.1
N10 C9 H9B 114.1
C8 C9 H9B 114.1
H9A C9 H9B 111.3
C16 N10 N11 116.88(9)
C16 N10 C9 117.61(9)
N11 N10 C9 89.80(8)
C12 N11 C8 129.47(10)
C12 N11 N10 119.91(9)
C8 N11 N10 92.19(8)
O12 C12 O13 126.57(11)
O12 C12 N11 124.72(11)
O13 C12 N11 108.59(10)
C12 O13 C14 114.69(9)
O13 C14 C15 107.29(10)
O13 C14 H14A 110.3
C15 C14 H14A 110.3
O13 C14 H14B 110.3
C15 C14 H14B 110.3
H14A C14 H14B 108.5
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O16 C16 O17 127.24(12)
O16 C16 N10 121.74(11)
O17 C16 N10 110.90(10)
C16 O17 C18 116.71(10)
O17 C18 C19 110.65(12)
O17 C18 H18A 109.5
C19 C18 H18A 109.5
O17 C18 H18B 109.5
C19 C18 H18B 109.5
H18A C18 H18B 108.1
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3834(18)
C1 C6 1.3999(17)
C1 H1A 0.9500
C2 C3 1.3872(18)
C2 H2A 0.9500
C3 C4 1.3863(18)
C3 H3A 0.9500
C4 C5 1.3860(17)
C4 H4A 0.9500
C5 C6 1.4003(17)
C5 H5A 0.9500
C6 C7 1.4657(16)
C7 C8 1.3290(17)
C7 H7A 0.9500
C8 N11 1.4347(15)
C8 C9 1.5104(16)
C9 N10 1.5010(15)
C9 H9A 0.9900
C9 H9B 0.9900
N10 C16 1.4008(16)
N10 N11 1.4521(13)
N11 C12 1.3887(15)
O12 C12 1.2045(14)
C12 O13 1.3372(14)
O13 C14 1.4613(14)
C14 C15 1.5001(18)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
O16 C16 1.2053(15)
C16 O17 1.3267(15)
O17 C18 1.4566(16)
C18 C19 1.473(2)
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
|
1502056.cif | #------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502056.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502056
loop_
_publ_author_name
'Zhang, Xiaobing'
'Fu, Chunling'
'Ma, Shengming'
_publ_section_title
;
Highly stereoselective facile synthesis of 2-acetoxy-1,3(E)-alkadienes
via a Rh(I)-catalyzed isomerization of 2,3-allenyl carboxylates.
;
_journal_issue 8
_journal_name_full 'Organic letters'
_journal_page_first 1920
_journal_page_last 1923
_journal_paper_doi 10.1021/ol200198z
_journal_volume 13
_journal_year 2011
_chemical_formula_sum 'C21 H21 N O4'
_chemical_formula_weight 351.39
_chemical_name_systematic
;
?
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 96.638(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.7254(7)
_cell_length_b 8.2025(7)
_cell_length_c 29.583(3)
_cell_measurement_temperature 173(2)
_cell_volume 1862.0(3)
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0364
_diffrn_reflns_av_sigmaI/netI 0.0239
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 30
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_number 20256
_diffrn_reflns_theta_full 25.01
_diffrn_reflns_theta_max 25.01
_diffrn_reflns_theta_min 2.58
_exptl_absorpt_coefficient_mu 0.087
_exptl_absorpt_correction_T_max 0.9871
_exptl_absorpt_correction_T_min 0.9761
_exptl_absorpt_correction_type multi-scan
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.253
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 744
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.188
_refine_diff_density_min -0.242
_refine_diff_density_rms 0.048
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.185
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 243
_refine_ls_number_reflns 3269
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.185
_refine_ls_R_factor_all 0.0694
_refine_ls_R_factor_gt 0.0608
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+2.8753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1451
_refine_ls_wR_factor_ref 0.1500
_reflns_number_gt 2783
_reflns_number_total 3269
_reflns_threshold_expression >2sigma(I)
_cod_data_source_file ol200198z_si_001.cif
_cod_data_source_block z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_sg_symbol_H-M P2(1)/c
_cod_database_code 1502056
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.5836(3) 0.4527(3) -0.07885(8) 0.0351(6) Uani 1 1 d .
O1 O -0.0583(3) 0.2003(3) 0.02270(7) 0.0452(5) Uani 1 1 d .
O2 O 0.1737(2) 0.1243(2) 0.07100(6) 0.0356(5) Uani 1 1 d .
O3 O 0.5282(3) 0.5413(3) -0.11023(9) 0.0615(7) Uani 1 1 d .
O4 O 0.7379(3) 0.4224(3) -0.06943(8) 0.0465(6) Uani 1 1 d .
C1 C 0.4000(3) 0.2090(3) 0.01003(9) 0.0323(6) Uani 1 1 d .
H1A H 0.4378 0.1324 0.0332 0.039 Uiso 1 1 calc R
C2 C 0.5180(3) 0.2708(3) -0.01738(9) 0.0321(6) Uani 1 1 d .
H2A H 0.6365 0.2371 -0.0136 0.039 Uiso 1 1 calc R
C3 C 0.4582(3) 0.3830(3) -0.05043(9) 0.0306(6) Uani 1 1 d .
C4 C 0.2875(4) 0.4343(3) -0.05703(9) 0.0344(6) Uani 1 1 d .
H4A H 0.2503 0.5115 -0.0801 0.041 Uiso 1 1 calc R
C5 C 0.1718(4) 0.3712(3) -0.02952(9) 0.0340(6) Uani 1 1 d .
H5A H 0.0535 0.4051 -0.0335 0.041 Uiso 1 1 calc R
C6 C 0.2274(3) 0.2582(3) 0.00403(9) 0.0302(6) Uani 1 1 d .
C7 C 0.0967(4) 0.1925(3) 0.03255(9) 0.0329(6) Uani 1 1 d .
C8 C 0.0624(4) 0.0496(3) 0.09986(9) 0.0342(6) Uani 1 1 d .
C9 C 0.0502(4) -0.1113(4) 0.09658(12) 0.0437(8) Uani 1 1 d .
H9A H 0.111(4) -0.168(4) 0.0737(12) 0.054(10) Uiso 1 1 d .
H9B H -0.016(4) -0.169(4) 0.1178(11) 0.051(10) Uiso 1 1 d .
C10 C -0.0167(3) 0.1563(3) 0.13152(9) 0.0306(6) Uani 1 1 d .
C11 C 0.0443(4) 0.3102(3) 0.13761(9) 0.0356(7) Uani 1 1 d .
H11A H 0.1332 0.3406 0.1196 0.043 Uiso 1 1 calc R
C12 C -0.0088(4) 0.4368(3) 0.16842(9) 0.0398(7) Uani 1 1 d .
C13 C 0.1210(5) 0.5485(4) 0.18591(11) 0.0518(9) Uani 1 1 d .
H13A H 0.2353 0.5412 0.1772 0.062 Uiso 1 1 calc R
C14 C 0.0807(7) 0.6692(4) 0.21585(12) 0.0644(11) Uani 1 1 d .
H14A H 0.1691 0.7429 0.2279 0.077 Uiso 1 1 calc R
C15 C -0.0831(7) 0.6841(5) 0.22833(12) 0.0691(12) Uani 1 1 d .
H15A H -0.1077 0.7663 0.2493 0.083 Uiso 1 1 calc R
C16 C -0.2127(6) 0.5794(4) 0.21034(11) 0.0609(10) Uani 1 1 d .
H16A H -0.3277 0.5911 0.2183 0.073 Uiso 1 1 calc R
C17 C -0.1753(5) 0.4569(4) 0.18062(10) 0.0477(8) Uani 1 1 d .
H17A H -0.2656 0.3854 0.1684 0.057 Uiso 1 1 calc R
C18 C -0.1566(4) 0.0789(3) 0.15544(9) 0.0343(6) Uani 1 1 d .
H18A H -0.1791 0.1480 0.1816 0.041 Uiso 1 1 calc R
H18B H -0.1152 -0.0286 0.1675 0.041 Uiso 1 1 calc R
C19 C -0.3268(4) 0.0557(4) 0.12409(11) 0.0416(7) Uani 1 1 d .
H19A H -0.3790 0.1641 0.1167 0.050 Uiso 1 1 calc R
H19B H -0.2999 0.0055 0.0953 0.050 Uiso 1 1 calc R
C20 C -0.4591(5) -0.0493(5) 0.14429(13) 0.0602(10) Uani 1 1 d .
H20A H -0.5599 -0.0672 0.1210 0.072 Uiso 1 1 calc R
H20B H -0.4061 -0.1570 0.1523 0.072 Uiso 1 1 calc R
C21 C -0.5233(6) 0.0230(8) 0.18600(17) 0.108(2) Uani 1 1 d .
H21A H -0.6081 -0.0509 0.1973 0.162 Uiso 1 1 calc R
H21B H -0.5789 0.1283 0.1783 0.162 Uiso 1 1 calc R
H21C H -0.4247 0.0388 0.2096 0.162 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0335(13) 0.0262(12) 0.0453(14) -0.0017(11) 0.0032(11) -0.0005(10)
O1 0.0301(11) 0.0575(14) 0.0478(13) 0.0081(11) 0.0038(9) 0.0055(10)
O2 0.0321(10) 0.0385(11) 0.0361(11) 0.0018(9) 0.0036(8) 0.0024(9)
O3 0.0426(13) 0.0741(17) 0.0673(16) 0.0365(14) 0.0038(11) 0.0036(12)
O4 0.0319(11) 0.0420(12) 0.0662(15) 0.0081(11) 0.0080(10) 0.0056(9)
C1 0.0311(14) 0.0271(14) 0.0377(15) -0.0007(11) -0.0005(12) 0.0060(11)
C2 0.0257(13) 0.0283(14) 0.0418(16) -0.0038(12) 0.0016(12) 0.0062(11)
C3 0.0317(14) 0.0239(13) 0.0352(15) -0.0067(11) -0.0002(11) 0.0007(11)
C4 0.0341(15) 0.0299(14) 0.0379(15) 0.0016(12) -0.0020(12) 0.0067(12)
C5 0.0283(14) 0.0341(15) 0.0388(16) -0.0022(12) 0.0000(12) 0.0084(12)
C6 0.0297(14) 0.0264(13) 0.0338(14) -0.0063(11) 0.0007(11) 0.0038(11)
C7 0.0315(15) 0.0306(14) 0.0359(15) -0.0051(12) 0.0011(12) 0.0060(12)
C8 0.0329(15) 0.0330(15) 0.0359(15) -0.0005(12) -0.0003(12) 0.0022(12)
C9 0.0435(18) 0.0327(16) 0.056(2) -0.0055(15) 0.0080(16) 0.0008(14)
C10 0.0298(14) 0.0278(14) 0.0335(14) 0.0027(11) 0.0005(11) 0.0014(11)
C11 0.0431(16) 0.0292(15) 0.0346(15) 0.0023(12) 0.0046(12) -0.0012(13)
C12 0.067(2) 0.0236(14) 0.0280(15) 0.0043(11) 0.0009(14) -0.0001(14)
C13 0.082(3) 0.0333(17) 0.0393(17) 0.0024(14) 0.0022(16) -0.0113(17)
C14 0.117(4) 0.0337(18) 0.0400(19) -0.0033(15) -0.004(2) -0.013(2)
C15 0.128(4) 0.038(2) 0.040(2) -0.0067(16) 0.003(2) 0.017(2)
C16 0.092(3) 0.049(2) 0.0411(19) -0.0016(16) 0.0045(19) 0.026(2)
C17 0.067(2) 0.0370(17) 0.0384(17) 0.0011(14) 0.0005(15) 0.0135(16)
C18 0.0390(16) 0.0269(14) 0.0372(15) 0.0039(12) 0.0046(12) 0.0011(12)
C19 0.0404(17) 0.0374(16) 0.0463(18) 0.0021(14) 0.0021(13) 0.0029(14)
C20 0.0429(19) 0.061(2) 0.075(3) 0.009(2) 0.0023(17) -0.0099(18)
C21 0.069(3) 0.175(6) 0.087(3) -0.010(4) 0.034(3) -0.037(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 N1 O4 123.0(2)
O3 N1 C3 118.1(2)
O4 N1 C3 118.8(2)
C7 O2 C8 116.7(2)
C2 C1 C6 120.5(3)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C3 C2 C1 118.0(2)
C3 C2 H2A 121.0
C1 C2 H2A 121.0
C4 C3 C2 122.7(3)
C4 C3 N1 118.9(2)
C2 C3 N1 118.3(2)
C3 C4 C5 118.5(3)
C3 C4 H4A 120.7
C5 C4 H4A 120.7
C4 C5 C6 120.3(2)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
C1 C6 C5 120.0(3)
C1 C6 C7 121.9(2)
C5 C6 C7 118.2(2)
O1 C7 O2 124.0(3)
O1 C7 C6 124.4(3)
O2 C7 C6 111.5(2)
C9 C8 O2 115.4(3)
C9 C8 C10 127.6(3)
O2 C8 C10 116.9(2)
C8 C9 H9A 119(2)
C8 C9 H9B 118(2)
H9A C9 H9B 122(3)
C11 C10 C8 118.6(3)
C11 C10 C18 126.3(3)
C8 C10 C18 115.1(2)
C10 C11 C12 128.6(3)
C10 C11 H11A 115.7
C12 C11 H11A 115.7
C17 C12 C13 117.9(3)
C17 C12 C11 125.4(3)
C13 C12 C11 116.7(3)
C14 C13 C12 119.7(4)
C14 C13 H13A 120.2
C12 C13 H13A 120.2
C15 C14 C13 121.4(4)
C15 C14 H14A 119.3
C13 C14 H14A 119.3
C14 C15 C16 119.6(3)
C14 C15 H15A 120.2
C16 C15 H15A 120.2
C15 C16 C17 120.0(4)
C15 C16 H16A 120.0
C17 C16 H16A 120.0
C12 C17 C16 121.3(4)
C12 C17 H17A 119.4
C16 C17 H17A 119.4
C10 C18 C19 112.5(2)
C10 C18 H18A 109.1
C19 C18 H18A 109.1
C10 C18 H18B 109.1
C19 C18 H18B 109.1
H18A C18 H18B 107.8
C20 C19 C18 113.8(3)
C20 C19 H19A 108.8
C18 C19 H19A 108.8
C20 C19 H19B 108.8
C18 C19 H19B 108.8
H19A C19 H19B 107.7
C21 C20 C19 113.7(4)
C21 C20 H20A 108.8
C19 C20 H20A 108.8
C21 C20 H20B 108.8
C19 C20 H20B 108.8
H20A C20 H20B 107.7
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O3 1.217(3)
N1 O4 1.218(3)
N1 C3 1.470(4)
O1 C7 1.201(3)
O2 C7 1.343(3)
O2 C8 1.419(3)
C1 C2 1.384(4)
C1 C6 1.384(4)
C1 H1A 0.9500
C2 C3 1.383(4)
C2 H2A 0.9500
C3 C4 1.377(4)
C4 C5 1.377(4)
C4 H4A 0.9500
C5 C6 1.389(4)
C5 H5A 0.9500
C6 C7 1.490(4)
C8 C9 1.326(4)
C8 C10 1.466(4)
C9 H9A 0.98(4)
C9 H9B 0.97(3)
C10 C11 1.352(4)
C10 C18 1.499(4)
C11 C12 1.471(4)
C11 H11A 0.9500
C12 C17 1.386(5)
C12 C13 1.412(4)
C13 C14 1.387(5)
C13 H13A 0.9500
C14 C15 1.364(6)
C14 H14A 0.9500
C15 C16 1.379(6)
C15 H15A 0.9500
C16 C17 1.387(5)
C16 H16A 0.9500
C17 H17A 0.9500
C18 C19 1.531(4)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.512(4)
C19 H19A 0.9900
C19 H19B 0.9900
C20 C21 1.504(6)
C20 H20A 0.9900
C20 H20B 0.9900
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.4(4)
C1 C2 C3 C4 -0.2(4)
C1 C2 C3 N1 178.3(2)
O3 N1 C3 C4 -7.1(4)
O4 N1 C3 C4 171.2(3)
O3 N1 C3 C2 174.2(3)
O4 N1 C3 C2 -7.4(4)
C2 C3 C4 C5 0.1(4)
N1 C3 C4 C5 -178.5(2)
C3 C4 C5 C6 -0.1(4)
C2 C1 C6 C5 -0.5(4)
C2 C1 C6 C7 179.2(2)
C4 C5 C6 C1 0.3(4)
C4 C5 C6 C7 -179.4(2)
C8 O2 C7 O1 3.8(4)
C8 O2 C7 C6 -176.7(2)
C1 C6 C7 O1 -162.1(3)
C5 C6 C7 O1 17.6(4)
C1 C6 C7 O2 18.4(4)
C5 C6 C7 O2 -161.9(2)
C7 O2 C8 C9 99.9(3)
C7 O2 C8 C10 -83.7(3)
C9 C8 C10 C11 163.7(3)
O2 C8 C10 C11 -12.2(4)
C9 C8 C10 C18 -14.3(4)
O2 C8 C10 C18 169.8(2)
C8 C10 C11 C12 -177.5(3)
C18 C10 C11 C12 0.3(5)
C10 C11 C12 C17 -32.9(5)
C10 C11 C12 C13 148.7(3)
C17 C12 C13 C14 2.7(4)
C11 C12 C13 C14 -178.8(3)
C12 C13 C14 C15 -1.0(5)
C13 C14 C15 C16 -1.1(6)
C14 C15 C16 C17 1.6(5)
C13 C12 C17 C16 -2.2(4)
C11 C12 C17 C16 179.4(3)
C15 C16 C17 C12 0.1(5)
C11 C10 C18 C19 108.1(3)
C8 C10 C18 C19 -74.0(3)
C10 C18 C19 C20 169.3(3)
C18 C19 C20 C21 64.1(4)
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