# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Shigeru Shimada' 'Shuangfeng Yin.' _publ_contact_author_name 'Shigeru Shimada' _publ_contact_author_email S-SHIMADA@AIST.GO.JP _publ_section_title ; Synthesis and structure of bismuth compounds bearing a sulfur-bridged bis(phenolato) ligand and their catalytic application to solvent-free synthesis of propylene carbonate from CO2 and propylene oxide ; _publ_contact_author_address ; National Institute of Advanced Industrial Science and Technology, Tukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan ; _publ_contact_author_fax +81-29-861-4511 _publ_contact_author_phone +81-29-861-6257 _publ_requested_journal 'Chemical Communications' # Attachment 'Compounds_2a_and_2b.cif' data_Compound-2a _database_code_depnum_ccdc_archive 'CCDC 708754' _audit_creation_date 2008-07-20 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C23 H31 Bi O3 S ' _chemical_formula_moiety 'C23 H31 Bi O3 S ' _chemical_formula_weight 596.54 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.7696(5) _cell_length_b 10.1108(6) _cell_length_c 12.7225(7) _cell_angle_alpha 82.790(1) _cell_angle_beta 68.441(1) _cell_angle_gamma 84.105(1) _cell_volume 1157.36(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5119 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.3 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584.00 _exptl_absorpt_coefficient_mu 7.713 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.253 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 6996 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 28.26 _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.965 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4877 _reflns_number_gt 4551 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0747 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4877 _refine_ls_number_parameters 284 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[1.0000\s(Fo^2^) + 0.1200]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 2.54 _refine_diff_density_min -2.73 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Bi(1) Bi 0.12550(2) 0.07693(2) 0.05858(2) 0.02258(4) Uani 1.00 1 d . . . S(1) S 0.38775(13) 0.05545(12) 0.12278(10) 0.0242(2) Uani 1.00 1 d . . . O(1) O 0.0575(3) 0.0955(4) 0.2374(3) 0.0305(9) Uani 1.00 1 d . . . O(2) O 0.1992(4) -0.1230(3) 0.0657(3) 0.0315(10) Uani 1.00 1 d . . . O(3) O -0.0882(3) 0.0030(3) 0.1066(3) 0.0283(9) Uani 1.00 1 d . . . C(1) C 0.1351(5) 0.1442(4) 0.2899(4) 0.0239(11) Uani 1.00 1 d . . . C(2) C 0.0606(5) 0.2142(4) 0.3876(4) 0.0252(11) Uani 1.00 1 d . . . C(3) C 0.1458(6) 0.2536(5) 0.4435(4) 0.0319(13) Uani 1.00 1 d . . . C(4) C 0.2985(6) 0.2310(5) 0.4083(4) 0.0329(14) Uani 1.00 1 d . . . C(5) C 0.3697(5) 0.1679(5) 0.3113(4) 0.0278(12) Uani 1.00 1 d . . . C(6) C 0.2895(5) 0.1252(4) 0.2529(4) 0.0221(11) Uani 1.00 1 d . . . C(7) C 0.3777(5) -0.1200(4) 0.1546(4) 0.0223(11) Uani 1.00 1 d . . . C(8) C 0.4696(5) -0.1913(5) 0.2068(4) 0.0294(13) Uani 1.00 1 d . . . C(9) C 0.4770(6) -0.3285(5) 0.2206(4) 0.0322(13) Uani 1.00 1 d . . . C(10) C 0.3905(5) -0.3940(5) 0.1797(4) 0.0293(12) Uani 1.00 1 d . . . C(11) C 0.2972(5) -0.3287(5) 0.1274(4) 0.0249(11) Uani 1.00 1 d . . . C(12) C 0.2889(5) -0.1878(4) 0.1164(3) 0.0218(11) Uani 1.00 1 d . . . C(13) C -0.1075(5) 0.2429(5) 0.4314(4) 0.0301(13) Uani 1.00 1 d . . . C(14) C -0.1828(6) 0.1112(6) 0.4776(5) 0.0375(14) Uani 1.00 1 d . . . C(15) C -0.1576(6) 0.3134(7) 0.3362(6) 0.0481(18) Uani 1.00 1 d . . . C(16) C -0.1581(7) 0.3330(7) 0.5289(6) 0.056(2) Uani 1.00 1 d . . . C(17) C 0.3808(7) 0.2712(8) 0.4783(6) 0.055(2) Uani 1.00 1 d . . . C(18) C 0.5733(7) -0.4062(6) 0.2795(5) 0.0460(18) Uani 1.00 1 d . . . C(19) C 0.2073(6) -0.4056(5) 0.0805(5) 0.0320(14) Uani 1.00 1 d . . . C(20) C 0.2357(7) -0.5572(5) 0.0984(6) 0.0461(18) Uani 1.00 1 d . . . C(21) C 0.2493(7) -0.3662(6) -0.0476(5) 0.0419(17) Uani 1.00 1 d . . . C(22) C 0.0416(6) -0.3724(6) 0.1424(6) 0.0461(18) Uani 1.00 1 d . . . C(23) C -0.1715(6) -0.0513(7) 0.2183(4) 0.0440(17) Uani 1.00 1 d . . . H(1) H 0.0969 0.2982 0.5100 0.038 Uiso 1.00 1 c R . . H(2) H 0.4740 0.1536 0.2840 0.034 Uiso 1.00 1 c R . . H(3) H 0.5279 -0.1441 0.2332 0.036 Uiso 1.00 1 c R . . H(4) H 0.3957 -0.4889 0.1884 0.035 Uiso 1.00 1 c R . . H(5) H -0.1501 0.0517 0.4199 0.042 Uiso 1.00 1 c R . . H(6) H -0.1582 0.0724 0.5409 0.042 Uiso 1.00 1 c R . . H(7) H -0.2867 0.1278 0.5006 0.042 Uiso 1.00 1 c R . . H(8) H -0.2577 0.3459 0.3669 0.054 Uiso 1.00 1 c R . . H(9) H -0.0975 0.3859 0.2990 0.054 Uiso 1.00 1 c R . . H(10) H -0.1477 0.2514 0.2832 0.054 Uiso 1.00 1 c R . . H(11) H -0.2595 0.3600 0.5468 0.063 Uiso 1.00 1 c R . . H(12) H -0.1440 0.2852 0.5937 0.063 Uiso 1.00 1 c R . . H(13) H -0.1016 0.4097 0.5064 0.063 Uiso 1.00 1 c R . . H(14) H 0.4818 0.2413 0.4470 0.071 Uiso 1.00 1 c R . . H(15) H 0.3730 0.3656 0.4783 0.071 Uiso 1.00 1 c R . . H(16) H 0.3390 0.2314 0.5539 0.071 Uiso 1.00 1 c R . . H(17) H 0.5344 -0.3933 0.3580 0.060 Uiso 1.00 1 c R . . H(18) H 0.5768 -0.4985 0.2707 0.060 Uiso 1.00 1 c R . . H(19) H 0.6700 -0.3753 0.2464 0.060 Uiso 1.00 1 c R . . H(20) H 0.3362 -0.5809 0.0568 0.059 Uiso 1.00 1 c R . . H(21) H 0.2147 -0.5830 0.1769 0.059 Uiso 1.00 1 c R . . H(22) H 0.1743 -0.6015 0.0728 0.059 Uiso 1.00 1 c R . . H(23) H 0.2319 -0.2725 -0.0606 0.055 Uiso 1.00 1 c R . . H(24) H 0.3506 -0.3903 -0.0857 0.055 Uiso 1.00 1 c R . . H(25) H 0.1911 -0.4113 -0.0758 0.055 Uiso 1.00 1 c R . . H(26) H 0.0215 -0.2785 0.1346 0.056 Uiso 1.00 1 c R . . H(27) H -0.0140 -0.4151 0.1104 0.056 Uiso 1.00 1 c R . . H(28) H 0.0153 -0.4030 0.2206 0.056 Uiso 1.00 1 c R . . H(29) H -0.1065 -0.0863 0.2566 0.053 Uiso 1.00 1 c R . . H(30) H -0.2362 0.0170 0.2587 0.053 Uiso 1.00 1 c R . . H(31) H -0.2273 -0.1207 0.2141 0.053 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 Bi(1) 0.02768(10) 0.02190(10) 0.02179(10) -0.00496(7) -0.01274(7) -0.00052(6) S(1) 0.0222(5) 0.0299(6) 0.0195(5) -0.0094(4) -0.0037(4) -0.0047(4) O(1) 0.0246(17) 0.050(2) 0.0211(17) -0.0110(15) -0.0093(14) -0.0087(15) O(2) 0.037(2) 0.0256(18) 0.044(2) -0.0008(15) -0.0275(18) -0.0066(15) O(3) 0.0284(17) 0.0364(19) 0.0246(17) -0.0093(15) -0.0152(15) 0.0040(14) C(1) 0.025(2) 0.024(2) 0.026(2) -0.0026(18) -0.013(2) -0.0017(18) C(2) 0.027(2) 0.024(2) 0.023(2) -0.0013(18) -0.0066(19) -0.0004(18) C(3) 0.035(2) 0.032(2) 0.028(2) -0.002(2) -0.008(2) -0.009(2) C(4) 0.035(2) 0.035(2) 0.035(2) -0.007(2) -0.017(2) -0.011(2) C(5) 0.025(2) 0.030(2) 0.030(2) -0.006(2) -0.009(2) -0.007(2) C(6) 0.024(2) 0.022(2) 0.020(2) -0.0049(17) -0.0072(18) -0.0012(17) C(7) 0.019(2) 0.026(2) 0.021(2) -0.0015(17) -0.0044(18) -0.0081(18) C(8) 0.021(2) 0.045(3) 0.025(2) 0.004(2) -0.009(2) -0.015(2) C(9) 0.031(2) 0.041(3) 0.027(2) 0.012(2) -0.015(2) -0.013(2) C(10) 0.033(2) 0.029(2) 0.025(2) 0.007(2) -0.009(2) -0.008(2) C(11) 0.024(2) 0.028(2) 0.022(2) -0.0027(19) -0.0071(19) -0.0052(19) C(12) 0.020(2) 0.026(2) 0.019(2) -0.0019(18) -0.0059(18) -0.0030(17) C(13) 0.025(2) 0.032(2) 0.028(2) -0.001(2) -0.004(2) 0.001(2) C(14) 0.028(2) 0.043(3) 0.035(3) -0.006(2) -0.004(2) 0.004(2) C(15) 0.027(2) 0.051(3) 0.057(4) 0.001(2) -0.012(2) 0.016(3) C(16) 0.038(3) 0.058(4) 0.062(4) 0.006(3) -0.001(3) -0.030(3) C(17) 0.050(3) 0.081(5) 0.047(3) -0.012(3) -0.022(3) -0.029(3) C(18) 0.054(3) 0.049(3) 0.046(3) 0.018(3) -0.033(3) -0.016(2) C(19) 0.038(2) 0.020(2) 0.045(3) -0.004(2) -0.021(2) -0.005(2) C(20) 0.056(3) 0.025(2) 0.066(4) -0.004(2) -0.030(3) -0.009(2) C(21) 0.056(3) 0.039(3) 0.043(3) -0.002(2) -0.027(3) -0.017(2) C(22) 0.035(3) 0.036(3) 0.070(4) -0.014(2) -0.019(3) -0.002(2) C(23) 0.034(2) 0.072(4) 0.026(2) -0.024(2) -0.008(2) -0.003(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) S(1) 2.9424(14) yes . . Bi(1) O(1) 2.151(3) yes . . Bi(1) O(2) 2.078(3) yes . . Bi(1) O(3) 2.135(3) yes . . Bi(1) O(3) 2.500(4) yes . 2_555 S(1) C(6) 1.773(4) yes . . S(1) C(7) 1.774(4) yes . . O(1) C(1) 1.339(7) yes . . O(2) C(12) 1.343(6) yes . . O(3) C(23) 1.425(6) yes . . C(1) C(2) 1.423(6) yes . . C(1) C(6) 1.406(6) yes . . C(2) C(3) 1.390(9) yes . . C(2) C(13) 1.536(7) yes . . C(3) C(4) 1.394(7) yes . . C(4) C(5) 1.374(7) yes . . C(4) C(17) 1.513(11) yes . . C(5) C(6) 1.390(8) yes . . C(7) C(8) 1.396(7) yes . . C(7) C(12) 1.406(8) yes . . C(8) C(9) 1.374(8) yes . . C(9) C(10) 1.396(9) yes . . C(9) C(18) 1.511(10) yes . . C(10) C(11) 1.386(8) yes . . C(11) C(12) 1.411(6) yes . . C(11) C(19) 1.540(9) yes . . C(13) C(14) 1.532(7) yes . . C(13) C(15) 1.538(9) yes . . C(13) C(16) 1.533(10) yes . . C(19) C(20) 1.533(7) yes . . C(19) C(21) 1.538(8) yes . . C(19) C(22) 1.539(7) yes . . C(3) H(1) 0.950 no . . C(5) H(2) 0.950 no . . C(8) H(3) 0.950 no . . C(10) H(4) 0.950 no . . C(14) H(5) 0.950 no . . C(14) H(6) 0.950 no . . C(14) H(7) 0.950 no . . C(15) H(8) 0.950 no . . C(15) H(9) 0.950 no . . C(15) H(10) 0.950 no . . C(16) H(11) 0.950 no . . C(16) H(12) 0.950 no . . C(16) H(13) 0.950 no . . C(17) H(14) 0.950 no . . C(17) H(15) 0.950 no . . C(17) H(16) 0.950 no . . C(18) H(17) 0.950 no . . C(18) H(18) 0.950 no . . C(18) H(19) 0.950 no . . C(20) H(20) 0.950 no . . C(20) H(21) 0.950 no . . C(20) H(22) 0.950 no . . C(21) H(23) 0.950 no . . C(21) H(24) 0.950 no . . C(21) H(25) 0.950 no . . C(22) H(26) 0.950 no . . C(22) H(27) 0.950 no . . C(22) H(28) 0.950 no . . C(23) H(29) 0.950 no . . C(23) H(30) 0.950 no . . C(23) H(31) 0.950 no . . 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_2 _geom_angle_site_symmetry_3 S(1) Bi(1) O(1) 70.80(10) yes . . . S(1) Bi(1) O(2) 71.88(13) yes . . . S(1) Bi(1) O(3) 142.48(10) yes . . . S(1) Bi(1) O(3) 130.65(8) yes . . 2_555 O(1) Bi(1) O(2) 96.37(15) yes . . . O(1) Bi(1) O(3) 83.09(14) yes . . . O(1) Bi(1) O(3) 151.28(13) yes . . 2_555 O(2) Bi(1) O(3) 85.22(14) yes . . . O(2) Bi(1) O(3) 77.17(15) yes . . 2_555 O(3) Bi(1) O(3) 68.59(12) yes . . 2_555 Bi(1) S(1) C(6) 92.68(18) yes . . . Bi(1) S(1) C(7) 91.75(18) yes . . . C(6) S(1) C(7) 105.8(2) yes . . . Bi(1) O(1) C(1) 126.6(2) yes . . . Bi(1) O(2) C(12) 130.5(3) yes . . . Bi(1) O(3) Bi(1) 111.41(13) yes . . 2_555 Bi(1) O(3) C(23) 124.2(4) yes . . . Bi(1) O(3) C(23) 118.9(3) yes 2_555 . . O(1) C(1) C(2) 119.8(4) yes . . . O(1) C(1) C(6) 121.7(4) yes . . . C(2) C(1) C(6) 118.5(5) yes . . . C(1) C(2) C(3) 117.2(4) yes . . . C(1) C(2) C(13) 121.7(5) yes . . . C(3) C(2) C(13) 121.0(4) yes . . . C(2) C(3) C(4) 124.0(5) yes . . . C(3) C(4) C(5) 118.1(6) yes . . . C(3) C(4) C(17) 120.1(5) yes . . . C(5) C(4) C(17) 121.7(5) yes . . . C(4) C(5) C(6) 120.2(4) yes . . . S(1) C(6) C(1) 119.7(4) yes . . . S(1) C(6) C(5) 118.3(3) yes . . . C(1) C(6) C(5) 121.9(4) yes . . . S(1) C(7) C(8) 119.7(4) yes . . . S(1) C(7) C(12) 119.6(3) yes . . . C(8) C(7) C(12) 120.3(4) yes . . . C(7) C(8) C(9) 121.2(5) yes . . . C(8) C(9) C(10) 117.6(5) yes . . . C(8) C(9) C(18) 121.5(6) yes . . . C(10) C(9) C(18) 121.0(5) yes . . . C(9) C(10) C(11) 123.9(5) yes . . . C(10) C(11) C(12) 117.5(5) yes . . . C(10) C(11) C(19) 121.9(4) yes . . . C(12) C(11) C(19) 120.5(4) yes . . . O(2) C(12) C(7) 122.2(4) yes . . . O(2) C(12) C(11) 118.3(5) yes . . . C(7) C(12) C(11) 119.5(4) yes . . . C(2) C(13) C(14) 109.2(4) yes . . . C(2) C(13) C(15) 110.7(4) yes . . . C(2) C(13) C(16) 111.4(5) yes . . . C(14) C(13) C(15) 110.1(5) yes . . . C(14) C(13) C(16) 107.4(4) yes . . . C(15) C(13) C(16) 107.9(5) yes . . . C(11) C(19) C(20) 112.0(5) yes . . . C(11) C(19) C(21) 109.7(4) yes . . . C(11) C(19) C(22) 109.5(4) yes . . . C(20) C(19) C(21) 107.9(5) yes . . . C(20) C(19) C(22) 107.7(4) yes . . . C(21) C(19) C(22) 109.9(5) yes . . . C(2) C(3) H(1) 118.0 no . . . C(4) C(3) H(1) 118.0 no . . . C(4) C(5) H(2) 120.0 no . . . C(6) C(5) H(2) 119.8 no . . . C(7) C(8) H(3) 119.4 no . . . C(9) C(8) H(3) 119.4 no . . . C(9) C(10) H(4) 118.0 no . . . C(11) C(10) H(4) 118.1 no . . . C(13) C(14) H(5) 109.4 no . . . C(13) C(14) H(6) 109.5 no . . . C(13) C(14) H(7) 109.5 no . . . H(5) C(14) H(6) 109.5 no . . . H(5) C(14) H(7) 109.5 no . . . H(6) C(14) H(7) 109.5 no . . . C(13) C(15) H(8) 110.1 no . . . C(13) C(15) H(9) 109.4 no . . . C(13) C(15) H(10) 109.0 no . . . H(8) C(15) H(9) 109.5 no . . . H(8) C(15) H(10) 109.5 no . . . H(9) C(15) H(10) 109.5 no . . . C(13) C(16) H(11) 109.7 no . . . C(13) C(16) H(12) 109.4 no . . . C(13) C(16) H(13) 109.3 no . . . H(11) C(16) H(12) 109.5 no . . . H(11) C(16) H(13) 109.5 no . . . H(12) C(16) H(13) 109.5 no . . . C(4) C(17) H(14) 109.7 no . . . C(4) C(17) H(15) 109.7 no . . . C(4) C(17) H(16) 109.1 no . . . H(14) C(17) H(15) 109.5 no . . . H(14) C(17) H(16) 109.5 no . . . H(15) C(17) H(16) 109.5 no . . . C(9) C(18) H(17) 109.8 no . . . C(9) C(18) H(18) 109.6 no . . . C(9) C(18) H(19) 109.0 no . . . H(17) C(18) H(18) 109.5 no . . . H(17) C(18) H(19) 109.5 no . . . H(18) C(18) H(19) 109.5 no . . . C(19) C(20) H(20) 109.3 no . . . C(19) C(20) H(21) 109.2 no . . . C(19) C(20) H(22) 109.9 no . . . H(20) C(20) H(21) 109.5 no . . . H(20) C(20) H(22) 109.5 no . . . H(21) C(20) H(22) 109.5 no . . . C(19) C(21) H(23) 109.3 no . . . C(19) C(21) H(24) 109.5 no . . . C(19) C(21) H(25) 109.6 no . . . H(23) C(21) H(24) 109.5 no . . . H(23) C(21) H(25) 109.5 no . . . H(24) C(21) H(25) 109.5 no . . . C(19) C(22) H(26) 109.4 no . . . C(19) C(22) H(27) 109.7 no . . . C(19) C(22) H(28) 109.3 no . . . H(26) C(22) H(27) 109.5 no . . . H(26) C(22) H(28) 109.5 no . . . H(27) C(22) H(28) 109.5 no . . . O(3) C(23) H(29) 109.6 no . . . O(3) C(23) H(30) 109.3 no . . . O(3) C(23) H(31) 109.5 no . . . H(29) C(23) H(30) 109.5 no . . . H(29) C(23) H(31) 109.5 no . . . H(30) C(23) H(31) 109.5 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_Compound-2b _database_code_depnum_ccdc_archive 'CCDC 708755' _audit_creation_date 2008-07-20 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C26 H36 Bi I O3 S ' _chemical_formula_moiety 'C23 H28 Bi I O2 S, C4 H8 O ' _chemical_formula_weight 764.51 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 29.9918(18) _cell_length_b 9.1349(5) _cell_length_c 20.2035(12) _cell_angle_alpha 90.000 _cell_angle_beta 95.083(1) _cell_angle_gamma 90.000 _cell_volume 5513.4(6) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4754 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944.00 _exptl_absorpt_coefficient_mu 7.604 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.363 _exptl_absorpt_correction_T_max 0.504 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 16341 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_theta_max 28.27 _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6168 _reflns_number_gt 4869 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0884 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 6168 _refine_ls_number_parameters 335 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.4000\s(Fo^2^) + 0.1000]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 1.78 _refine_diff_density_min -2.89 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.474 1.812 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Bi(1) Bi 0.073990(10) -0.01147(3) 0.470230(10) 0.03736(6) Uani 1.00 1 d . . . I(1) I 0.002200(10) 0.20056(7) 0.42577(2) 0.05930(14) Uani 1.00 1 d . . . S(1) S 0.16170(5) -0.12277(16) 0.49083(6) 0.0316(3) Uani 1.00 1 d . . . O(1) O 0.10760(12) 0.0605(4) 0.38849(18) 0.0350(10) Uani 1.00 1 d . . . O(2) O 0.10881(12) 0.1458(4) 0.53230(17) 0.0322(9) Uani 1.00 1 d . . . O(3) O 0.06002(17) -0.2450(6) 0.3923(2) 0.0719(17) Uani 1.00 1 d . . . C(1) C 0.14036(16) -0.0188(5) 0.3636(2) 0.0270(12) Uani 1.00 1 d . . . C(2) C 0.14518(17) -0.0135(5) 0.2947(2) 0.0270(12) Uani 1.00 1 d . . . C(3) C 0.17983(17) -0.0959(6) 0.2722(2) 0.0290(13) Uani 1.00 1 d . . . C(4) C 0.20935(18) -0.1818(6) 0.3127(2) 0.0336(14) Uani 1.00 1 d . . . C(5) C 0.20410(18) -0.1841(6) 0.3799(2) 0.0327(14) Uani 1.00 1 d . . . C(6) C 0.17013(17) -0.1023(5) 0.4050(2) 0.0271(12) Uani 1.00 1 d . . . C(7) C 0.18306(18) 0.0418(6) 0.5295(2) 0.0285(13) Uani 1.00 1 d . . . C(8) C 0.22886(18) 0.0480(6) 0.5472(2) 0.0307(13) Uani 1.00 1 d . . . C(9) C 0.24711(18) 0.1691(6) 0.5803(2) 0.0316(13) Uani 1.00 1 d . . . C(10) C 0.21859(18) 0.2835(6) 0.5933(2) 0.0308(13) Uani 1.00 1 d . . . C(11) C 0.17245(18) 0.2831(6) 0.5759(2) 0.0283(12) Uani 1.00 1 d . . . C(12) C 0.15366(17) 0.1548(6) 0.5448(2) 0.0286(13) Uani 1.00 1 d . . . C(13) C 0.11214(17) 0.0729(6) 0.2466(2) 0.0281(13) Uani 1.00 1 d . . . C(14) C 0.1120(2) 0.2357(6) 0.2652(3) 0.0434(17) Uani 1.00 1 d . . . C(15) C 0.06494(19) 0.0072(7) 0.2485(3) 0.0439(17) Uani 1.00 1 d . . . C(16) C 0.1246(2) 0.0631(6) 0.1749(2) 0.0335(14) Uani 1.00 1 d . . . C(17) C 0.2453(2) -0.2733(8) 0.2844(3) 0.0488(18) Uani 1.00 1 d . . . C(18) C 0.29626(19) 0.1770(7) 0.6016(3) 0.0434(17) Uani 1.00 1 d . . . C(19) C 0.14318(19) 0.4144(6) 0.5915(2) 0.0340(14) Uani 1.00 1 d . . . C(20) C 0.1713(2) 0.5435(7) 0.6206(3) 0.0487(19) Uani 1.00 1 d . . . C(21) C 0.1108(2) 0.3700(7) 0.6427(3) 0.0430(17) Uani 1.00 1 d . . . C(22) C 0.1172(2) 0.4714(7) 0.5282(3) 0.0500(19) Uani 1.00 1 d . . . C(23) C 0.0127(2) -0.2839(12) 0.3819(5) 0.089(3) Uani 1.00 1 d . . . C(24) C 0.0124(4) -0.4234(18) 0.3829(10) 0.067(5) Uani 0.50 1 d P . . C(25) C 0.0566(4) -0.4722(13) 0.3514(8) 0.049(4) Uani 0.50 1 d P . . C(26) C 0.0858(2) -0.3521(9) 0.3604(3) 0.061(2) Uani 1.00 1 d . . . C(27) C 0.0072(4) -0.3719(17) 0.3216(7) 0.054(4) Uani 0.50 1 d P . . C(28) C 0.0511(5) -0.432(2) 0.3052(8) 0.064(5) Uani 0.50 1 d P . . H(1) H 0.1836 -0.0935 0.2260 0.035 Uiso 1.00 1 c R . . H(2) H 0.2236 -0.2413 0.4090 0.039 Uiso 1.00 1 c R . . H(3) H 0.2475 -0.0309 0.5364 0.037 Uiso 1.00 1 c R . . H(4) H 0.2312 0.3674 0.6156 0.037 Uiso 1.00 1 c R . . H(5) H 0.0922 0.2906 0.2330 0.052 Uiso 1.00 1 c R . . H(6) H 0.1017 0.2471 0.3097 0.052 Uiso 1.00 1 c R . . H(7) H 0.1426 0.2733 0.2652 0.052 Uiso 1.00 1 c R . . H(8) H 0.0603 -0.0693 0.2146 0.053 Uiso 1.00 1 c R . . H(9) H 0.0619 -0.0353 0.2925 0.053 Uiso 1.00 1 c R . . H(10) H 0.0425 0.0843 0.2397 0.053 Uiso 1.00 1 c R . . H(11) H 0.1079 0.1373 0.1480 0.040 Uiso 1.00 1 c R . . H(12) H 0.1568 0.0805 0.1739 0.040 Uiso 1.00 1 c R . . H(13) H 0.1171 -0.0344 0.1570 0.040 Uiso 1.00 1 c R . . H(14) H 0.2677 -0.2087 0.2675 0.058 Uiso 1.00 1 c R . . H(15) H 0.2596 -0.3359 0.3195 0.059 Uiso 1.00 1 c R . . H(16) H 0.2318 -0.3344 0.2482 0.059 Uiso 1.00 1 c R . . H(17) H 0.3083 0.0777 0.6081 0.052 Uiso 1.00 1 c R . . H(18) H 0.3117 0.2269 0.5673 0.052 Uiso 1.00 1 c R . . H(19) H 0.3009 0.2315 0.6434 0.052 Uiso 1.00 1 c R . . H(20) H 0.1867 0.5149 0.6634 0.058 Uiso 1.00 1 c R . . H(21) H 0.1935 0.5707 0.5899 0.058 Uiso 1.00 1 c R . . H(22) H 0.1517 0.6273 0.6269 0.058 Uiso 1.00 1 c R . . H(23) H 0.1279 0.3492 0.6852 0.052 Uiso 1.00 1 c R . . H(24) H 0.0897 0.4500 0.6485 0.052 Uiso 1.00 1 c R . . H(25) H 0.0942 0.2822 0.6273 0.053 Uiso 1.00 1 c R . . H(26) H 0.0980 0.5534 0.5390 0.059 Uiso 1.00 1 c R . . H(27) H 0.1383 0.5043 0.4969 0.059 Uiso 1.00 1 c R . . H(28) H 0.0985 0.3924 0.5079 0.059 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 Bi(1) 0.02697(11) 0.05828(16) 0.02829(11) -0.01116(10) 0.01059(8) -0.01650(10) I(1) 0.0309(2) 0.1037(4) 0.0435(2) 0.0027(2) 0.00434(17) -0.0191(2) S(1) 0.0404(7) 0.0317(7) 0.0227(5) -0.0041(5) 0.0036(5) 0.0013(5) O(1) 0.0282(19) 0.053(2) 0.0252(18) 0.0125(18) 0.0073(15) -0.0060(17) O(2) 0.0276(18) 0.043(2) 0.0264(18) -0.0022(16) 0.0042(14) -0.0067(16) O(3) 0.051(2) 0.098(4) 0.068(3) -0.021(2) 0.016(2) -0.052(3) C(1) 0.021(2) 0.035(2) 0.025(2) 0.000(2) 0.0040(19) -0.003(2) C(2) 0.027(2) 0.026(2) 0.028(2) -0.002(2) 0.005(2) -0.003(2) C(3) 0.026(2) 0.036(2) 0.024(2) -0.003(2) 0.0027(19) -0.005(2) C(4) 0.027(2) 0.039(3) 0.035(2) 0.004(2) 0.002(2) -0.009(2) C(5) 0.034(2) 0.030(2) 0.034(2) 0.003(2) -0.000(2) -0.001(2) C(6) 0.031(2) 0.029(2) 0.021(2) -0.004(2) 0.0054(19) -0.002(2) C(7) 0.031(2) 0.034(2) 0.019(2) -0.003(2) 0.001(2) 0.001(2) C(8) 0.034(2) 0.035(2) 0.023(2) 0.001(2) 0.004(2) 0.009(2) C(9) 0.032(2) 0.042(3) 0.020(2) -0.006(2) 0.003(2) 0.005(2) C(10) 0.034(2) 0.040(3) 0.019(2) -0.007(2) 0.002(2) 0.002(2) C(11) 0.033(2) 0.034(2) 0.019(2) -0.000(2) 0.0057(19) 0.003(2) C(12) 0.030(2) 0.037(2) 0.019(2) -0.002(2) 0.0012(19) 0.004(2) C(13) 0.026(2) 0.036(2) 0.023(2) 0.002(2) 0.0024(19) -0.003(2) C(14) 0.057(3) 0.036(3) 0.036(3) 0.011(2) -0.002(2) 0.002(2) C(15) 0.027(2) 0.073(4) 0.031(2) -0.002(2) 0.000(2) 0.007(2) C(16) 0.040(3) 0.036(3) 0.025(2) -0.000(2) 0.003(2) 0.001(2) C(17) 0.038(3) 0.064(4) 0.044(3) 0.013(3) 0.002(2) -0.016(3) C(18) 0.033(3) 0.059(4) 0.038(3) -0.006(2) -0.001(2) 0.003(2) C(19) 0.036(2) 0.036(3) 0.030(2) -0.002(2) 0.002(2) -0.002(2) C(20) 0.054(4) 0.036(3) 0.057(4) -0.003(3) 0.003(3) -0.006(3) C(21) 0.046(3) 0.041(3) 0.044(3) 0.006(2) 0.016(2) -0.009(2) C(22) 0.056(4) 0.046(3) 0.047(3) 0.010(3) -0.004(3) 0.005(3) C(23) 0.050(4) 0.116(8) 0.102(7) -0.026(5) 0.015(4) -0.072(6) C(24) 0.028(6) 0.052(9) 0.120(15) 0.006(6) 0.008(8) 0.007(9) C(25) 0.047(7) 0.024(6) 0.072(10) 0.005(5) -0.020(7) -0.004(6) C(26) 0.060(4) 0.063(4) 0.059(4) 0.012(3) 0.007(3) -0.006(3) C(27) 0.054(8) 0.065(9) 0.044(7) -0.010(7) 0.004(6) -0.023(7) C(28) 0.040(7) 0.097(13) 0.057(9) 0.012(8) 0.011(7) -0.022(9) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) I(1) 2.9751(5) yes . . Bi(1) S(1) 2.8165(15) yes . . Bi(1) O(1) 2.114(3) yes . . Bi(1) O(2) 2.120(3) yes . . S(1) C(6) 1.784(5) yes . . S(1) C(7) 1.787(5) yes . . O(1) C(1) 1.353(6) yes . . O(2) C(12) 1.349(6) yes . . O(3) C(23) 1.459(9) yes . . O(3) C(26) 1.433(10) yes . . C(1) C(2) 1.413(7) yes . . C(1) C(6) 1.395(6) yes . . C(2) C(3) 1.392(7) yes . . C(2) C(13) 1.542(7) yes . . C(3) C(4) 1.394(7) yes . . C(4) C(5) 1.379(7) yes . . C(4) C(17) 1.515(8) yes . . C(5) C(6) 1.395(7) yes . . C(7) C(8) 1.390(7) yes . . C(7) C(12) 1.410(7) yes . . C(8) C(9) 1.380(7) yes . . C(9) C(10) 1.390(8) yes . . C(9) C(18) 1.501(7) yes . . C(10) C(11) 1.397(7) yes . . C(11) C(12) 1.422(7) yes . . C(11) C(19) 1.535(8) yes . . C(13) C(14) 1.534(8) yes . . C(13) C(15) 1.541(7) yes . . C(13) C(16) 1.529(7) yes . . C(19) C(20) 1.537(8) yes . . C(19) C(21) 1.536(8) yes . . C(19) C(22) 1.529(8) yes . . C(23) C(24) 1.27(2) yes . . C(23) C(27) 1.457(18) yes . . C(24) C(25) 1.58(2) yes . . C(25) C(26) 1.405(15) yes . . C(26) C(28) 1.628(18) yes . . C(27) C(28) 1.49(2) yes . . C(3) H(1) 0.950 no . . C(5) H(2) 0.950 no . . C(8) H(3) 0.950 no . . C(10) H(4) 0.950 no . . C(14) H(5) 0.980 no . . C(14) H(6) 0.980 no . . C(14) H(7) 0.980 no . . C(15) H(8) 0.980 no . . C(15) H(9) 0.980 no . . C(15) H(10) 0.980 no . . C(16) H(11) 0.980 no . . C(16) H(12) 0.980 no . . C(16) H(13) 0.980 no . . C(17) H(14) 0.980 no . . C(17) H(15) 0.980 no . . C(17) H(16) 0.980 no . . C(18) H(17) 0.980 no . . C(18) H(18) 0.980 no . . C(18) H(19) 0.980 no . . C(20) H(20) 0.980 no . . C(20) H(21) 0.980 no . . C(20) H(22) 0.980 no . . C(21) H(23) 0.980 no . . C(21) H(24) 0.980 no . . C(21) H(25) 0.980 no . . C(22) H(26) 0.980 no . . C(22) H(27) 0.980 no . . C(22) H(28) 0.980 no . . 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_2 _geom_angle_site_symmetry_3 I(1) Bi(1) S(1) 157.08(3) yes . . . I(1) Bi(1) O(1) 86.80(10) yes . . . I(1) Bi(1) O(2) 92.45(10) yes . . . S(1) Bi(1) O(1) 73.98(10) yes . . . S(1) Bi(1) O(2) 75.67(10) yes . . . O(1) Bi(1) O(2) 90.42(14) yes . . . Bi(1) S(1) C(6) 91.69(17) yes . . . Bi(1) S(1) C(7) 93.14(18) yes . . . C(6) S(1) C(7) 105.1(2) yes . . . Bi(1) O(1) C(1) 122.4(3) yes . . . Bi(1) O(2) C(12) 125.6(3) yes . . . C(23) O(3) C(26) 109.0(6) yes . . . O(1) C(1) C(2) 119.3(4) yes . . . O(1) C(1) C(6) 121.1(4) yes . . . C(2) C(1) C(6) 119.6(4) yes . . . C(1) C(2) C(3) 116.6(4) yes . . . C(1) C(2) C(13) 121.5(4) yes . . . C(3) C(2) C(13) 121.8(4) yes . . . C(2) C(3) C(4) 124.5(4) yes . . . C(3) C(4) C(5) 117.7(5) yes . . . C(3) C(4) C(17) 121.7(5) yes . . . C(5) C(4) C(17) 120.6(5) yes . . . C(4) C(5) C(6) 120.0(4) yes . . . S(1) C(6) C(1) 120.1(3) yes . . . S(1) C(6) C(5) 118.0(3) yes . . . C(1) C(6) C(5) 121.6(4) yes . . . S(1) C(7) C(8) 117.1(4) yes . . . S(1) C(7) C(12) 120.3(3) yes . . . C(8) C(7) C(12) 122.5(4) yes . . . C(7) C(8) C(9) 119.9(5) yes . . . C(8) C(9) C(10) 118.0(4) yes . . . C(8) C(9) C(18) 121.0(5) yes . . . C(10) C(9) C(18) 121.0(5) yes . . . C(9) C(10) C(11) 124.3(5) yes . . . C(10) C(11) C(12) 117.3(4) yes . . . C(10) C(11) C(19) 121.2(4) yes . . . C(12) C(11) C(19) 121.5(4) yes . . . O(2) C(12) C(7) 123.2(4) yes . . . O(2) C(12) C(11) 118.9(4) yes . . . C(7) C(12) C(11) 118.0(4) yes . . . C(2) C(13) C(14) 110.9(4) yes . . . C(2) C(13) C(15) 109.0(4) yes . . . C(2) C(13) C(16) 111.7(4) yes . . . C(14) C(13) C(15) 110.4(4) yes . . . C(14) C(13) C(16) 107.2(4) yes . . . C(15) C(13) C(16) 107.6(4) yes . . . C(11) C(19) C(20) 111.9(4) yes . . . C(11) C(19) C(21) 109.8(4) yes . . . C(11) C(19) C(22) 110.8(4) yes . . . C(20) C(19) C(21) 107.7(4) yes . . . C(20) C(19) C(22) 106.3(5) yes . . . C(21) C(19) C(22) 110.3(5) yes . . . O(3) C(23) C(24) 104.5(9) yes . . . O(3) C(23) C(27) 107.0(8) yes . . . C(23) C(24) C(25) 105.5(12) yes . . . C(24) C(25) C(26) 105.2(10) yes . . . O(3) C(26) C(25) 103.7(8) yes . . . O(3) C(26) C(28) 106.0(7) yes . . . C(23) C(27) C(28) 110.5(11) yes . . . C(26) C(28) C(27) 101.9(12) yes . . . C(2) C(3) H(1) 117.8 no . . . C(4) C(3) H(1) 117.8 no . . . C(4) C(5) H(2) 120.0 no . . . C(6) C(5) H(2) 119.9 no . . . C(7) C(8) H(3) 120.0 no . . . C(9) C(8) H(3) 120.2 no . . . C(9) C(10) H(4) 118.1 no . . . C(11) C(10) H(4) 117.7 no . . . C(13) C(14) H(5) 110.3 no . . . C(13) C(14) H(6) 109.6 no . . . C(13) C(14) H(7) 108.4 no . . . H(5) C(14) H(6) 109.5 no . . . H(5) C(14) H(7) 109.5 no . . . H(6) C(14) H(7) 109.5 no . . . C(13) C(15) H(8) 109.4 no . . . C(13) C(15) H(9) 109.6 no . . . C(13) C(15) H(10) 109.4 no . . . H(8) C(15) H(9) 109.5 no . . . H(8) C(15) H(10) 109.5 no . . . H(9) C(15) H(10) 109.5 no . . . C(13) C(16) H(11) 109.3 no . . . C(13) C(16) H(12) 109.5 no . . . C(13) C(16) H(13) 109.7 no . . . H(11) C(16) H(12) 109.5 no . . . H(11) C(16) H(13) 109.5 no . . . H(12) C(16) H(13) 109.5 no . . . C(4) C(17) H(14) 109.5 no . . . C(4) C(17) H(15) 109.3 no . . . C(4) C(17) H(16) 109.7 no . . . H(14) C(17) H(15) 109.5 no . . . H(14) C(17) H(16) 109.5 no . . . H(15) C(17) H(16) 109.5 no . . . C(9) C(18) H(17) 109.5 no . . . C(9) C(18) H(18) 109.4 no . . . C(9) C(18) H(19) 109.5 no . . . H(17) C(18) H(18) 109.5 no . . . H(17) C(18) H(19) 109.5 no . . . H(18) C(18) H(19) 109.5 no . . . C(19) C(20) H(20) 109.4 no . . . C(19) C(20) H(21) 109.5 no . . . C(19) C(20) H(22) 109.5 no . . . H(20) C(20) H(21) 109.5 no . . . H(20) C(20) H(22) 109.5 no . . . H(21) C(20) H(22) 109.5 no . . . C(19) C(21) H(23) 109.1 no . . . C(19) C(21) H(24) 109.7 no . . . C(19) C(21) H(25) 109.6 no . . . H(23) C(21) H(24) 109.5 no . . . H(23) C(21) H(25) 109.5 no . . . H(24) C(21) H(25) 109.5 no . . . C(19) C(22) H(26) 109.9 no . . . C(19) C(22) H(27) 109.4 no . . . C(19) C(22) H(28) 109.1 no . . . H(26) C(22) H(27) 109.5 no . . . H(26) C(22) H(28) 109.5 no . . . H(27) C(22) H(28) 109.5 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_1 _geom_contact_site_symmetry_2 Bi(1) I(1) 3.6703(5) ? . 3_556 Bi(1) O(3) 2.663(5) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================