# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Phil Andrews' _publ_contact_author_address ; Wellington Road Clayton Melbourne Victoria Australia 3800 ; _publ_contact_author_email phil.andrews@sci.monash.edu.au loop_ _publ_author_name P.Andrews M.Busse G.Deacon R.Ferrero P.Junk K.Huynh I.Kumar ; J.MacLellan ; # Attachment '- Compound 4.CIF' data_c:\crysta~1\crysta~1\katie\tolyl\jon90abs _database_code_depnum_ccdc_archive 'CCDC 775518' #TrackingRef '- Compound 4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H38 Bi2 O12 S4' _chemical_formula_weight 1256.90 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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' _cell_length_a 10.141(2) _cell_length_b 18.174(4) _cell_length_c 22.988(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.34(3) _cell_angle_gamma 90.00 _cell_volume 4202.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 8.625 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2773 _exptl_absorpt_correction_T_max 0.3781 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26600 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7393 _reflns_number_gt 5405 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7393 _refine_ls_number_parameters 527 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 Bi1 Bi 0.801863(17) 0.135685(12) 0.218288(9) 0.01530(7) Uani 1 1 d . . . Bi2 Bi 1.309410(18) 0.072825(13) 0.219603(9) 0.01664(7) Uani 1 1 d . . . S1 S 1.06187(12) 0.08968(9) 0.31714(6) 0.0181(4) Uani 1 1 d . . . S2 S 1.05596(12) 0.13838(9) 0.12550(6) 0.0176(4) Uani 1 1 d . . . S3 S 0.56380(12) 0.12037(9) 0.32061(6) 0.0165(3) Uani 1 1 d . . . S4 S 0.54054(12) 0.08501(9) 0.12051(6) 0.0181(4) Uani 1 1 d . . . O1 O 1.0008(3) 0.1544(2) 0.28402(16) 0.0209(10) Uani 1 1 d . . . O2 O 1.1990(3) 0.0796(2) 0.30380(17) 0.0246(11) Uani 1 1 d . . . O3 O 0.9800(3) 0.0258(2) 0.30945(17) 0.0310(11) Uani 1 1 d . . . O4 O 0.9202(3) 0.1571(2) 0.13582(16) 0.0258(11) Uani 1 1 d . . . O5 O 1.1015(3) 0.0710(2) 0.15866(16) 0.0216(10) Uani 1 1 d . . . O6 O 1.1495(3) 0.1985(2) 0.13827(16) 0.0238(10) Uani 1 1 d . . . O7 O 0.7001(3) 0.1317(2) 0.30522(16) 0.0223(11) Uani 1 1 d . . . O8 O 0.5055(3) 0.0532(2) 0.29066(16) 0.0212(10) Uani 1 1 d . . . O9 O 0.4787(3) 0.1834(2) 0.31146(16) 0.0234(10) Uani 1 1 d . . . O10 O 0.5798(3) 0.1439(2) 0.16388(16) 0.0183(9) Uani 1 1 d . . . O11 O 0.4173(3) 0.0497(2) 0.13573(16) 0.0255(10) Uani 1 1 d . . . O12 O 0.6457(3) 0.0333(2) 0.11421(16) 0.0276(11) Uani 1 1 d . . . C1 C 0.7853(5) 0.2572(4) 0.2201(2) 0.0229(15) Uani 1 1 d . . . C2 C 0.6679(5) 0.2917(4) 0.2294(2) 0.0216(15) Uani 1 1 d . . . H2 H 0.5923 0.2633 0.2357 0.026 Uiso 1 1 calc R . . C3 C 0.6611(5) 0.3677(4) 0.2296(2) 0.0210(15) Uani 1 1 d . . . H3 H 0.5801 0.3913 0.2354 0.025 Uiso 1 1 calc R . . C4 C 0.7712(5) 0.4098(4) 0.2215(2) 0.0243(15) Uani 1 1 d . . . H4 H 0.7662 0.4620 0.2220 0.029 Uiso 1 1 calc R . . C5 C 0.8888(5) 0.3749(4) 0.2126(3) 0.0266(16) Uani 1 1 d . . . H5 H 0.9646 0.4036 0.2070 0.032 Uiso 1 1 calc R . . C6 C 0.8966(5) 0.2994(4) 0.2117(2) 0.0225(15) Uani 1 1 d . . . H6 H 0.9774 0.2759 0.2054 0.027 Uiso 1 1 calc R . . C7 C 1.0834(5) 0.1141(4) 0.3916(2) 0.0203(15) Uani 1 1 d . . . C8 C 1.1916(6) 0.1569(4) 0.4142(3) 0.0315(17) Uani 1 1 d . . . H8 H 1.2536 0.1738 0.3895 0.038 Uiso 1 1 calc R . . C9 C 1.2071(7) 0.1744(4) 0.4731(3) 0.044(2) Uani 1 1 d . . . H9 H 1.2802 0.2042 0.4886 0.052 Uiso 1 1 calc R . . C10 C 1.1189(7) 0.1497(5) 0.5103(3) 0.049(2) Uani 1 1 d . . . C11 C 1.0124(7) 0.1070(5) 0.4859(3) 0.053(2) Uani 1 1 d . . . H11 H 0.9500 0.0898 0.5103 0.063 Uiso 1 1 calc R . . C12 C 0.9948(6) 0.0888(4) 0.4273(3) 0.0350(18) Uani 1 1 d . . . H12 H 0.9218 0.0589 0.4117 0.042 Uiso 1 1 calc R . . C13 C 1.1423(7) 0.1676(5) 0.5748(3) 0.068(3) Uani 1 1 d U . . H13A H 1.1326 0.2207 0.5803 0.082 Uiso 1 1 calc R . . H13B H 1.2322 0.1523 0.5910 0.082 Uiso 1 1 calc R . . H13C H 1.0771 0.1414 0.5951 0.082 Uiso 1 1 calc R . . C14 C 1.0464(5) 0.1167(4) 0.0509(2) 0.0201(14) Uani 1 1 d . . . C15 C 0.9519(6) 0.1525(4) 0.0115(3) 0.0365(18) Uani 1 1 d . . . H15 H 0.8864 0.1831 0.0252 0.044 Uiso 1 1 calc R . . C16 C 0.9555(6) 0.1425(4) -0.0481(3) 0.0386(19) Uani 1 1 d . . . H16 H 0.8915 0.1669 -0.0753 0.046 Uiso 1 1 calc R . . C17 C 1.0491(5) 0.0982(4) -0.0691(3) 0.0274(16) Uani 1 1 d . . . C18 C 1.1395(5) 0.0610(4) -0.0289(3) 0.0301(18) Uani 1 1 d . . . H18 H 1.2032 0.0293 -0.0427 0.036 Uiso 1 1 calc R . . C19 C 1.1385(5) 0.0691(4) 0.0307(3) 0.0284(17) Uani 1 1 d . . . H19 H 1.1997 0.0427 0.0577 0.034 Uiso 1 1 calc R . . C20 C 1.0557(6) 0.0914(4) -0.1342(2) 0.043(2) Uani 1 1 d . . . H20A H 0.9822 0.0605 -0.1521 0.051 Uiso 1 1 calc R . . H20B H 1.1405 0.0688 -0.1406 0.051 Uiso 1 1 calc R . . H20C H 1.0488 0.1403 -0.1522 0.051 Uiso 1 1 calc R . . C21 C 0.5884(5) 0.1006(4) 0.3962(2) 0.0181(14) Uani 1 1 d . . . C22 C 0.6396(5) 0.0330(4) 0.4164(3) 0.0317(17) Uani 1 1 d . . . H22 H 0.6560 -0.0043 0.3892 0.038 Uiso 1 1 calc R . . C23 C 0.6664(5) 0.0202(4) 0.4760(3) 0.0369(19) Uani 1 1 d . . . H23 H 0.7015 -0.0261 0.4895 0.044 Uiso 1 1 calc R . . C24 C 0.6428(5) 0.0739(4) 0.5164(3) 0.0344(19) Uani 1 1 d . . . C25 C 0.5904(5) 0.1406(4) 0.4948(3) 0.0351(19) Uani 1 1 d . . . H25 H 0.5717 0.1778 0.5217 0.042 Uiso 1 1 calc R . . C26 C 0.5647(5) 0.1542(4) 0.4352(3) 0.0284(16) Uani 1 1 d . . . H26 H 0.5307 0.2006 0.4214 0.034 Uiso 1 1 calc R . . C27 C 0.6778(6) 0.0614(5) 0.5811(3) 0.053(2) Uani 1 1 d . . . H27A H 0.6590 0.0101 0.5904 0.063 Uiso 1 1 calc R . . H27B H 0.6248 0.0942 0.6027 0.063 Uiso 1 1 calc R . . H27C H 0.7726 0.0715 0.5924 0.063 Uiso 1 1 calc R . . C28 C 0.4921(5) 0.1280(4) 0.0531(3) 0.0224(15) Uani 1 1 d . . . C29 C 0.4047(5) 0.1869(4) 0.0493(3) 0.0279(16) Uani 1 1 d . . . H29 H 0.3758 0.2063 0.0840 0.033 Uiso 1 1 calc R . . C30 C 0.3595(5) 0.2175(4) -0.0041(3) 0.0333(18) Uani 1 1 d . . . H30 H 0.3008 0.2584 -0.0061 0.040 Uiso 1 1 calc R . . C31 C 0.3986(5) 0.1892(4) -0.0555(3) 0.0285(16) Uani 1 1 d . . . C32 C 0.4837(6) 0.1305(4) -0.0513(3) 0.040(2) Uani 1 1 d . . . H32 H 0.5101 0.1102 -0.0861 0.048 Uiso 1 1 calc R . . C33 C 0.5319(6) 0.1002(4) 0.0021(3) 0.0362(18) Uani 1 1 d . . . H33 H 0.5926 0.0601 0.0039 0.043 Uiso 1 1 calc R . . C34 C 0.3462(6) 0.2221(4) -0.1148(3) 0.046(2) Uani 1 1 d . . . H34A H 0.4078 0.2600 -0.1251 0.055 Uiso 1 1 calc R . . H34B H 0.2587 0.2440 -0.1129 0.055 Uiso 1 1 calc R . . H34C H 0.3385 0.1833 -0.1447 0.055 Uiso 1 1 calc R . . C35 C 1.2829(5) -0.0487(4) 0.2223(2) 0.0225(15) Uani 1 1 d . . . C36 C 1.3212(6) -0.0919(4) 0.1782(3) 0.0403(19) Uani 1 1 d . . . H36 H 1.3540 -0.0694 0.1456 0.048 Uiso 1 1 calc R . . C37 C 1.3125(6) -0.1678(4) 0.1808(3) 0.043(2) Uani 1 1 d . . . H37 H 1.3426 -0.1971 0.1509 0.052 Uiso 1 1 calc R . . C38 C 1.2605(5) -0.2007(4) 0.2264(3) 0.0331(18) Uani 1 1 d . . . H38 H 1.2522 -0.2527 0.2275 0.040 Uiso 1 1 calc R . . C39 C 1.2206(6) -0.1590(4) 0.2703(3) 0.0346(18) Uani 1 1 d . . . H39 H 1.1851 -0.1817 0.3021 0.041 Uiso 1 1 calc R . . C40 C 1.2324(5) -0.0834(4) 0.2681(3) 0.0272(16) Uani 1 1 d . . . H40 H 1.2051 -0.0546 0.2989 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 Bi1 0.01276(11) 0.01728(16) 0.01529(13) -0.00049(11) -0.00042(8) 0.00073(9) Bi2 0.01436(11) 0.01772(16) 0.01682(13) -0.00144(11) -0.00193(8) 0.00054(9) S1 0.0136(7) 0.0193(10) 0.0208(8) -0.0021(7) -0.0004(6) 0.0002(6) S2 0.0158(7) 0.0234(11) 0.0134(8) -0.0013(7) 0.0012(5) 0.0004(6) S3 0.0134(7) 0.0187(10) 0.0168(8) 0.0020(7) 0.0003(5) 0.0001(6) S4 0.0175(7) 0.0205(10) 0.0161(8) -0.0020(7) 0.0014(6) -0.0004(6) O1 0.0197(19) 0.024(3) 0.018(2) 0.001(2) -0.0031(15) 0.0024(18) O2 0.0154(19) 0.036(3) 0.023(2) -0.004(2) 0.0026(16) 0.0030(18) O3 0.029(2) 0.021(3) 0.040(3) -0.001(2) -0.0082(18) -0.0033(19) O4 0.0186(19) 0.041(3) 0.018(2) 0.003(2) 0.0051(16) 0.0090(19) O5 0.0206(19) 0.023(3) 0.020(2) 0.003(2) -0.0022(16) 0.0003(17) O6 0.032(2) 0.019(3) 0.021(2) -0.006(2) 0.0045(16) -0.0043(19) O7 0.0138(18) 0.041(3) 0.012(2) 0.003(2) 0.0007(14) -0.0052(18) O8 0.0203(19) 0.018(3) 0.023(2) 0.001(2) -0.0037(16) 0.0009(18) O9 0.024(2) 0.021(3) 0.024(2) 0.001(2) -0.0036(16) 0.0031(18) O10 0.0216(19) 0.015(3) 0.017(2) -0.0028(19) -0.0010(15) 0.0034(17) O11 0.025(2) 0.035(3) 0.018(2) 0.001(2) 0.0045(16) -0.0096(19) O12 0.028(2) 0.030(3) 0.024(2) -0.004(2) 0.0029(17) 0.0116(19) C1 0.020(3) 0.030(4) 0.016(3) 0.000(3) -0.005(2) 0.002(3) C2 0.027(3) 0.026(5) 0.012(3) 0.003(3) 0.002(2) 0.000(3) C3 0.021(3) 0.026(5) 0.017(3) 0.001(3) 0.004(2) 0.006(3) C4 0.038(4) 0.013(4) 0.021(4) 0.003(3) -0.001(3) -0.001(3) C5 0.024(3) 0.026(5) 0.029(4) -0.007(3) -0.001(3) -0.008(3) C6 0.015(3) 0.022(4) 0.028(4) 0.000(3) -0.005(2) -0.001(3) C7 0.024(3) 0.021(4) 0.016(3) 0.003(3) 0.003(2) 0.002(3) C8 0.037(4) 0.032(5) 0.022(4) -0.006(3) -0.006(3) 0.000(3) C9 0.056(4) 0.038(6) 0.032(4) -0.012(4) -0.011(3) 0.012(4) C10 0.070(5) 0.061(7) 0.014(4) -0.002(4) -0.006(4) 0.046(5) C11 0.057(5) 0.075(7) 0.030(5) 0.017(5) 0.019(4) 0.027(5) C12 0.032(4) 0.049(6) 0.025(4) 0.005(4) 0.007(3) 0.006(3) C13 0.078(4) 0.073(5) 0.051(4) -0.008(4) 0.002(3) 0.025(4) C14 0.020(3) 0.023(4) 0.016(3) -0.001(3) -0.001(2) -0.003(3) C15 0.043(4) 0.039(5) 0.025(4) -0.005(4) -0.004(3) 0.017(3) C16 0.058(4) 0.026(5) 0.027(4) 0.002(4) -0.009(3) 0.011(4) C17 0.031(3) 0.029(5) 0.021(4) -0.004(3) 0.001(3) -0.014(3) C18 0.018(3) 0.049(5) 0.024(4) -0.013(4) 0.007(2) -0.005(3) C19 0.015(3) 0.046(5) 0.023(4) -0.006(3) -0.005(2) 0.005(3) C20 0.052(4) 0.057(6) 0.018(4) -0.002(4) 0.002(3) -0.028(4) C21 0.009(3) 0.029(4) 0.016(3) -0.002(3) 0.001(2) -0.002(3) C22 0.028(3) 0.042(5) 0.027(4) 0.010(4) 0.009(3) 0.001(3) C23 0.038(4) 0.042(6) 0.029(4) 0.017(4) -0.001(3) 0.008(3) C24 0.019(3) 0.059(6) 0.025(4) 0.012(4) 0.001(3) -0.002(3) C25 0.035(4) 0.049(6) 0.020(4) -0.001(4) 0.000(3) -0.001(3) C26 0.023(3) 0.035(5) 0.026(4) 0.004(4) 0.000(3) 0.002(3) C27 0.042(4) 0.089(8) 0.028(4) 0.023(5) 0.004(3) -0.002(4) C28 0.021(3) 0.022(4) 0.023(4) -0.003(3) -0.001(2) -0.003(3) C29 0.027(3) 0.039(5) 0.018(4) 0.002(3) 0.002(2) 0.001(3) C30 0.032(3) 0.035(5) 0.032(4) 0.010(4) 0.001(3) 0.006(3) C31 0.028(3) 0.032(5) 0.025(4) 0.012(3) 0.000(3) -0.009(3) C32 0.052(4) 0.054(6) 0.016(4) -0.002(4) 0.013(3) 0.009(4) C33 0.042(4) 0.046(5) 0.022(4) 0.003(4) 0.010(3) 0.016(3) C34 0.048(4) 0.060(6) 0.026(4) 0.017(4) -0.006(3) -0.015(4) C35 0.013(3) 0.030(4) 0.022(4) 0.004(3) -0.008(2) 0.006(3) C36 0.062(5) 0.020(5) 0.043(5) -0.006(4) 0.023(4) -0.008(4) C37 0.060(5) 0.030(5) 0.045(5) -0.011(4) 0.024(4) -0.002(4) C38 0.014(3) 0.026(5) 0.057(5) 0.004(4) -0.004(3) -0.004(3) C39 0.041(4) 0.030(5) 0.034(4) 0.016(4) 0.010(3) 0.007(3) C40 0.036(3) 0.025(5) 0.022(4) 0.007(3) 0.005(3) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.215(7) . ? Bi1 O7 2.365(3) . ? Bi1 O1 2.386(3) . ? Bi1 O4 2.402(3) . ? Bi1 O10 2.437(3) . ? Bi2 C35 2.227(7) . ? Bi2 O2 2.360(4) . ? Bi2 O11 2.373(4) 1_655 ? Bi2 O5 2.377(3) . ? Bi2 O8 2.433(3) 1_655 ? S1 O3 1.426(4) . ? S1 O2 1.473(3) . ? S1 O1 1.492(4) . ? S1 C7 1.754(6) . ? S2 O6 1.452(4) . ? S2 O4 1.466(3) . ? S2 O5 1.484(4) . ? S2 C14 1.751(6) . ? S3 O9 1.434(4) . ? S3 O7 1.484(3) . ? S3 O8 1.486(4) . ? S3 C21 1.759(6) . ? S4 O12 1.442(4) . ? S4 O10 1.482(4) . ? S4 O11 1.486(4) . ? S4 C28 1.749(6) . ? O8 Bi2 2.433(3) 1_455 ? O11 Bi2 2.373(4) 1_455 ? C1 C2 1.387(7) . ? C1 C6 1.399(7) . ? C2 C3 1.382(8) . ? C2 H2 0.9500 . ? C3 C4 1.386(8) . ? C3 H3 0.9500 . ? C4 C5 1.388(8) . ? C4 H4 0.9500 . ? C5 C6 1.376(8) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.371(8) . ? C7 C8 1.390(8) . ? C8 C9 1.381(8) . ? C8 H8 0.9500 . ? C9 C10 1.388(10) . ? C9 H9 0.9500 . ? C10 C11 1.390(11) . ? C10 C13 1.507(9) . ? C11 C12 1.376(9) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.392(8) . ? C14 C19 1.394(8) . ? C15 C16 1.388(9) . ? C15 H15 0.9500 . ? C16 C17 1.378(8) . ? C16 H16 0.9500 . ? C17 C18 1.392(8) . ? C17 C20 1.513(8) . ? C18 C19 1.379(8) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C26 1.366(8) . ? C21 C22 1.391(9) . ? C22 C23 1.382(8) . ? C22 H22 0.9500 . ? C23 C24 1.390(9) . ? C23 H23 0.9500 . ? C24 C25 1.390(9) . ? C24 C27 1.501(8) . ? C25 C26 1.385(8) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C33 1.385(8) . ? C28 C29 1.385(8) . ? C29 C30 1.373(8) . ? C29 H29 0.9500 . ? C30 C31 1.391(8) . ? C30 H30 0.9500 . ? C31 C32 1.368(9) . ? C31 C34 1.521(8) . ? C32 C33 1.378(9) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.376(8) . ? C35 C40 1.382(8) . ? C36 C37 1.384(10) . ? C36 H36 0.9500 . ? C37 C38 1.370(9) . ? C37 H37 0.9500 . ? C38 C39 1.363(9) . ? C38 H38 0.9500 . ? C39 C40 1.379(9) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? 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 _geom_angle_publ_flag C1 Bi1 O7 88.40(17) . . ? C1 Bi1 O1 84.61(16) . . ? O7 Bi1 O1 83.94(12) . . ? C1 Bi1 O4 84.26(17) . . ? O7 Bi1 O4 171.19(14) . . ? O1 Bi1 O4 90.53(12) . . ? C1 Bi1 O10 83.19(16) . . ? O7 Bi1 O10 87.76(12) . . ? O1 Bi1 O10 165.42(13) . . ? O4 Bi1 O10 96.16(12) . . ? C35 Bi2 O2 87.56(18) . . ? C35 Bi2 O11 85.19(18) . 1_655 ? O2 Bi2 O11 172.76(15) . 1_655 ? C35 Bi2 O5 84.35(16) . . ? O2 Bi2 O5 90.34(12) . . ? O11 Bi2 O5 89.13(12) 1_655 . ? C35 Bi2 O8 85.83(16) . 1_655 ? O2 Bi2 O8 83.68(12) . 1_655 ? O11 Bi2 O8 95.59(12) 1_655 1_655 ? O5 Bi2 O8 168.71(13) . 1_655 ? O3 S1 O2 115.0(3) . . ? O3 S1 O1 112.5(2) . . ? O2 S1 O1 109.5(2) . . ? O3 S1 C7 109.0(3) . . ? O2 S1 C7 103.4(2) . . ? O1 S1 C7 106.9(3) . . ? O6 S2 O4 113.2(2) . . ? O6 S2 O5 111.4(2) . . ? O4 S2 O5 110.2(2) . . ? O6 S2 C14 108.7(3) . . ? O4 S2 C14 106.0(2) . . ? O5 S2 C14 107.0(3) . . ? O9 S3 O7 114.6(2) . . ? O9 S3 O8 113.1(2) . . ? O7 S3 O8 109.3(2) . . ? O9 S3 C21 108.3(3) . . ? O7 S3 C21 104.2(2) . . ? O8 S3 C21 106.7(3) . . ? O12 S4 O10 113.5(2) . . ? O12 S4 O11 113.4(3) . . ? O10 S4 O11 108.4(2) . . ? O12 S4 C28 109.3(3) . . ? O10 S4 C28 107.1(3) . . ? O11 S4 C28 104.6(2) . . ? S1 O1 Bi1 118.2(2) . . ? S1 O2 Bi2 137.5(2) . . ? S2 O4 Bi1 131.6(2) . . ? S2 O5 Bi2 119.1(2) . . ? S3 O7 Bi1 136.6(2) . . ? S3 O8 Bi2 115.7(2) . 1_455 ? S4 O10 Bi1 116.89(19) . . ? S4 O11 Bi2 127.1(2) . 1_455 ? C2 C1 C6 119.8(6) . . ? C2 C1 Bi1 121.5(4) . . ? C6 C1 Bi1 118.6(4) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.6(5) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.4(6) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.6(5) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.7(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 120.7(6) . . ? C12 C7 S1 119.3(5) . . ? C8 C7 S1 120.0(4) . . ? C9 C8 C7 118.7(6) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 121.8(7) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C10 C11 117.5(6) . . ? C9 C10 C13 120.2(8) . . ? C11 C10 C13 122.3(7) . . ? C12 C11 C10 121.8(7) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C7 C12 C11 119.4(7) . . ? C7 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 120.6(5) . . ? C15 C14 S2 118.6(5) . . ? C19 C14 S2 120.6(4) . . ? C16 C15 C14 118.6(6) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C17 C16 C15 121.9(6) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C18 118.4(6) . . ? C16 C17 C20 120.9(6) . . ? C18 C17 C20 120.6(6) . . ? C19 C18 C17 121.3(6) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C14 119.1(6) . . ? C18 C19 H19 120.5 . . ? C14 C19 H19 120.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C21 C22 120.0(6) . . ? C26 C21 S3 119.2(5) . . ? C22 C21 S3 120.6(5) . . ? C23 C22 C21 119.8(7) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 121.1(7) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C23 C24 C25 117.7(6) . . ? C23 C24 C27 121.1(7) . . ? C25 C24 C27 121.1(7) . . ? C26 C25 C24 121.5(7) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C21 C26 C25 119.8(7) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? 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 . . ? C33 C28 C29 118.9(6) . . ? C33 C28 S4 120.5(5) . . ? C29 C28 S4 120.4(5) . . ? C30 C29 C28 120.4(6) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.8(6) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C32 C31 C30 118.3(6) . . ? C32 C31 C34 120.9(6) . . ? C30 C31 C34 120.8(6) . . ? C31 C32 C33 121.6(6) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C32 C33 C28 120.0(6) . . ? C32 C33 H33 120.0 . . ? C28 C33 H33 120.0 . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 C40 117.9(7) . . ? C36 C35 Bi2 120.0(5) . . ? C40 C35 Bi2 122.1(5) . . ? C35 C36 C37 120.7(6) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C38 C37 C36 120.1(7) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? C39 C38 C37 120.2(7) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 C40 119.4(6) . . ? C38 C39 H39 120.3 . . ? C40 C39 H39 120.3 . . ? C39 C40 C35 121.7(6) . . ? C39 C40 H40 119.2 . . ? C35 C40 H40 119.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.418 _refine_diff_density_min -1.139 _refine_diff_density_rms 0.149 # Attachment '- Compound 5 new.cif' data_jon92 _database_code_depnum_ccdc_archive 'CCDC 775519' #TrackingRef '- Compound 5 new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H27 Bi O6 S2' _chemical_formula_sum 'C24 H27 Bi O6 S2' _chemical_formula_weight 684.56 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9654(4) _cell_length_b 10.0439(3) _cell_length_c 12.2092(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.073(2) _cell_angle_gamma 90.00 _cell_volume 1217.95(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6200 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 28.05 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 7.447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4947 _exptl_absorpt_correction_T_max 0.7071 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6200 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0959 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3480 _reflns_number_gt 2943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_cell_refinement 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_data_reduction 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Due to a problem with the collection strategy the completeness is somewhat low however the data parameter ratio is 14 to 1. Repeated attempts to recollect this structure were unsuccessful due to poor quality crystals. Anisotropic refinement for all aromatic carbons within ligand 1 were restrained to be the same as were atoms C20 and C21 in ligand 2. The ipso carbon, C1, of the phenyl ring was constrained to approximate isotropic behaviour. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc [0.00000+1.00000exp(2.20(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0000P)^2^+0.0000sin\q/\l] where P = 0.11100Fo^2^ + 0.88900Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.023(9) _refine_ls_number_reflns 3480 _refine_ls_number_parameters 253 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Bi1 Bi 0.04480(3) 0.30190(5) -0.00361(3) 0.01247(10) Uani 1 1 d . . . S1 S 0.0556(2) 0.0209(3) -0.1655(2) 0.0126(6) Uani 1 1 d . . . S2 S 0.1329(2) 0.0754(2) 0.2155(2) 0.0134(6) Uani 1 1 d . . . O1 O 0.0767(7) 0.1671(7) -0.1479(6) 0.0200(18) Uani 1 1 d . . . O2 O -0.0523(7) -0.0185(7) -0.1282(6) 0.0178(17) Uani 1 1 d . . . O3 O 0.1748(7) -0.0554(7) -0.1040(6) 0.0240(18) Uani 1 1 d . . . O4 O 0.1819(7) 0.1346(7) 0.1307(6) 0.0237(19) Uani 1 1 d . . . O5 O 0.0635(7) -0.0500(7) 0.1689(5) 0.0185(17) Uani 1 1 d . . . O6 O 0.0509(7) 0.1681(7) 0.2435(6) 0.0258(19) Uani 1 1 d . . . C1 C 0.2386(9) 0.3918(11) 0.0175(8) 0.014(2) Uani 1 1 d U . . C2 C 0.3471(8) 0.313(2) 0.0350(7) 0.018(2) Uani 1 1 d . . . H2 H 0.3377 0.2192 0.0322 0.022 Uiso 1 1 calc R . . C3 C 0.4695(10) 0.3688(13) 0.0566(10) 0.028(3) Uani 1 1 d . . . H3 H 0.5448 0.3133 0.0706 0.033 Uiso 1 1 calc R . . C4 C 0.4831(12) 0.5068(14) 0.0579(10) 0.030(3) Uani 1 1 d . . . H4 H 0.5672 0.5458 0.0714 0.036 Uiso 1 1 calc R . . C5 C 0.3742(11) 0.5859(12) 0.0395(9) 0.025(3) Uani 1 1 d . . . H5 H 0.3823 0.6800 0.0391 0.030 Uiso 1 1 calc R . . C6 C 0.2515(11) 0.5275(11) 0.0212(8) 0.023(3) Uani 1 1 d . . . H6 H 0.1767 0.5821 0.0113 0.027 Uiso 1 1 calc R . . C7 C -0.0113(5) -0.0025(6) -0.3248(3) 0.0154(9) Uani 1 1 d G . . C8 C -0.1325(4) 0.0596(5) -0.3958(4) 0.0154(9) Uani 1 1 d G . . C9 C -0.1911(4) 0.0416(6) -0.5204(4) 0.0154(9) Uani 1 1 d G . . H9 H -0.2740 0.0841 -0.5689 0.019 Uiso 1 1 calc R . . C10 C -0.1283(5) -0.0385(6) -0.5740(3) 0.0154(9) Uani 1 1 d G . . C11 C -0.0070(5) -0.1006(6) -0.5030(4) 0.0154(9) Uani 1 1 d G . . H11 H 0.0359 -0.1554 -0.5397 0.019 Uiso 1 1 calc R . . C12 C 0.0515(5) -0.0826(6) -0.3784(4) 0.0154(9) Uani 1 1 d G . . C13 C -0.2064(7) 0.1561(7) -0.3486(6) 0.023(3) Uani 1 1 d G . . H13A H -0.2894 0.1863 -0.4158 0.035 Uiso 1 1 calc R . . H13B H -0.1486 0.2330 -0.3114 0.035 Uiso 1 1 calc R . . H13C H -0.2287 0.1112 -0.2882 0.035 Uiso 1 1 calc R . . C14 C -0.1911(12) -0.0606(13) -0.7105(8) 0.033(3) Uani 1 1 d . . . H14A H -0.2880 -0.0431 -0.7437 0.050 Uiso 1 1 calc R . . H14B H -0.1760 -0.1529 -0.7278 0.050 Uiso 1 1 calc R . . H14C H -0.1495 -0.0001 -0.7478 0.050 Uiso 1 1 calc R . . C15 C 0.1845(9) -0.1557(10) -0.3096(10) 0.025(3) Uani 1 1 d . . . H15A H 0.2544 -0.0915 -0.2625 0.038 Uiso 1 1 calc R . . H15B H 0.2109 -0.2014 -0.3672 0.038 Uiso 1 1 calc R . . H15C H 0.1735 -0.2213 -0.2549 0.038 Uiso 1 1 calc R . . C16 C 0.2805(8) 0.0283(10) 0.3472(7) 0.008(2) Uani 1 1 d . . . C17 C 0.3757(9) -0.0545(10) 0.3321(8) 0.014(2) Uani 1 1 d . . . C18 C 0.4814(10) -0.1014(10) 0.4340(8) 0.017(2) Uani 1 1 d . . . H18 H 0.5460 -0.1577 0.4248 0.021 Uiso 1 1 calc R . . C19 C 0.4972(10) -0.0694(10) 0.5498(8) 0.013(2) Uani 1 1 d . . . C20 C 0.4022(9) 0.0143(10) 0.5614(8) 0.0114(15) Uani 1 1 d . . . H20 H 0.4121 0.0368 0.6403 0.014 Uiso 1 1 calc R . . C21 C 0.2933(9) 0.0665(10) 0.4624(8) 0.0114(15) Uani 1 1 d . . . C22 C 0.3663(11) -0.0983(11) 0.2112(9) 0.026(3) Uani 1 1 d . . . H22A H 0.4501 -0.1428 0.2219 0.039 Uiso 1 1 calc R . . H22B H 0.3518 -0.0205 0.1588 0.039 Uiso 1 1 calc R . . H22C H 0.2907 -0.1602 0.1741 0.039 Uiso 1 1 calc R . . C23 C 0.6084(10) -0.1310(11) 0.6591(8) 0.023(3) Uani 1 1 d . . . H23A H 0.6247 -0.0766 0.7305 0.034 Uiso 1 1 calc R . . H23B H 0.6908 -0.1354 0.6464 0.034 Uiso 1 1 calc R . . H23C H 0.5820 -0.2210 0.6713 0.034 Uiso 1 1 calc R . . C24 C 0.2025(9) 0.1605(11) 0.4902(8) 0.016(2) Uani 1 1 d . . . H24A H 0.2341 0.1681 0.5780 0.023 Uiso 1 1 calc R . . H24B H 0.1102 0.1259 0.4546 0.023 Uiso 1 1 calc R . . H24C H 0.2043 0.2484 0.4560 0.023 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 Bi1 0.01467(13) 0.01095(19) 0.01082(14) 0.0000(3) 0.00446(10) 0.0000(4) S1 0.0178(12) 0.0107(17) 0.0112(12) -0.0023(9) 0.0081(10) -0.0016(11) S2 0.0167(11) 0.0102(16) 0.0091(12) 0.0019(9) 0.0015(10) 0.0008(11) O1 0.036(4) 0.017(5) 0.011(4) -0.003(3) 0.014(3) -0.009(4) O2 0.022(4) 0.020(5) 0.014(4) -0.004(3) 0.010(3) -0.003(3) O3 0.023(4) 0.021(5) 0.022(4) -0.006(3) 0.004(3) 0.000(3) O4 0.019(4) 0.030(5) 0.020(4) 0.012(3) 0.006(3) -0.002(3) O5 0.027(4) 0.010(4) 0.012(4) 0.003(3) 0.002(3) 0.000(3) O6 0.025(4) 0.023(5) 0.022(4) -0.001(3) 0.002(3) 0.021(4) C1 0.016(4) 0.019(5) 0.007(3) -0.003(3) 0.006(3) 0.003(3) C2 0.025(4) 0.018(7) 0.015(4) 0.001(7) 0.011(3) 0.010(9) C3 0.015(5) 0.046(10) 0.032(6) -0.011(5) 0.019(5) -0.005(5) C4 0.036(7) 0.038(10) 0.024(6) -0.012(5) 0.020(5) -0.018(6) C5 0.034(6) 0.019(7) 0.025(6) -0.006(5) 0.015(5) 0.007(6) C6 0.030(6) 0.023(8) 0.017(5) -0.004(4) 0.012(5) -0.003(5) C7 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C8 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C9 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C10 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C11 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C12 0.0258(19) 0.011(3) 0.014(2) -0.0055(16) 0.0119(17) -0.0115(19) C13 0.026(6) 0.021(7) 0.017(5) 0.001(4) 0.004(5) 0.015(6) C14 0.050(7) 0.042(8) 0.017(6) -0.009(5) 0.023(5) -0.025(7) C15 0.023(5) 0.018(10) 0.039(7) -0.014(4) 0.017(5) -0.011(4) C16 0.003(4) 0.013(6) 0.006(4) 0.004(4) -0.001(3) -0.004(4) C17 0.015(5) 0.013(6) 0.013(5) -0.005(4) 0.007(4) -0.004(5) C18 0.023(5) 0.009(7) 0.021(6) 0.003(4) 0.010(4) -0.007(5) C19 0.022(5) 0.011(6) 0.010(5) -0.003(4) 0.010(4) 0.001(5) C20 0.020(3) 0.009(5) 0.009(3) -0.002(3) 0.009(3) -0.008(3) C21 0.020(3) 0.009(5) 0.009(3) -0.002(3) 0.009(3) -0.008(3) C22 0.030(6) 0.025(8) 0.021(6) -0.004(5) 0.009(5) 0.013(5) C23 0.020(5) 0.029(7) 0.015(5) 0.005(4) 0.004(4) -0.001(5) C24 0.015(5) 0.016(6) 0.017(5) -0.006(4) 0.009(4) -0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.221(10) . ? Bi1 O1 2.363(7) . ? Bi1 O5 2.380(6) 2 ? Bi1 O4 2.384(7) . ? Bi1 O2 2.396(7) 2 ? S1 O3 1.424(7) . ? S1 O1 1.489(8) . ? S1 O2 1.490(7) . ? S1 C7 1.779(4) . ? S2 O6 1.433(8) . ? S2 O5 1.456(7) . ? S2 O4 1.479(7) . ? S2 C16 1.795(8) . ? O2 Bi1 2.396(7) 2_545 ? O5 Bi1 2.380(6) 2_545 ? C1 C2 1.366(16) . ? C1 C6 1.369(16) . ? C2 C3 1.372(15) . ? C2 H2 0.9500 . ? C3 C4 1.393(17) . ? C3 H3 0.9500 . ? C4 C5 1.370(17) . ? C4 H4 0.9500 . ? C5 C6 1.397(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.3900 . ? C7 C12 1.3900 . ? C8 C9 1.3900 . ? C8 C13 1.5242 . ? C9 C10 1.3900 . ? C9 H9 0.9500 . ? C10 C11 1.3900 . ? C10 C14 1.526(10) . ? C11 C12 1.3900 . ? C11 H11 0.9500 . ? C12 C15 1.528(10) . ? 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 . ? C16 C21 1.406(12) . ? C16 C17 1.407(14) . ? C17 C18 1.375(12) . ? C17 C22 1.501(13) . ? C18 C19 1.387(13) . ? C18 H18 0.9500 . ? C19 C20 1.392(14) . ? C19 C23 1.507(12) . ? C20 C21 1.393(12) . ? C20 H20 0.9500 . ? C21 C24 1.512(14) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 . ? 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 _geom_angle_publ_flag C1 Bi1 O1 83.3(3) . . ? C1 Bi1 O5 87.3(3) . 2 ? O1 Bi1 O5 84.5(2) . 2 ? C1 Bi1 O4 85.0(3) . . ? O1 Bi1 O4 81.9(2) . . ? O5 Bi1 O4 165.1(2) 2 . ? C1 Bi1 O2 81.8(3) . 2 ? O1 Bi1 O2 163.5(2) . 2 ? O5 Bi1 O2 87.8(2) 2 2 ? O4 Bi1 O2 103.7(2) . 2 ? O3 S1 O1 113.7(4) . . ? O3 S1 O2 111.5(4) . . ? O1 S1 O2 108.2(5) . . ? O3 S1 C7 111.5(4) . . ? O1 S1 C7 104.7(3) . . ? O2 S1 C7 106.6(3) . . ? O6 S2 O5 112.3(5) . . ? O6 S2 O4 110.9(5) . . ? O5 S2 O4 111.0(4) . . ? O6 S2 C16 112.1(4) . . ? O5 S2 C16 104.2(4) . . ? O4 S2 C16 106.0(4) . . ? S1 O1 Bi1 127.6(4) . . ? S1 O2 Bi1 126.8(4) . 2_545 ? S2 O4 Bi1 117.1(4) . . ? S2 O5 Bi1 149.6(4) . 2_545 ? C2 C1 C6 119.9(12) . . ? C2 C1 Bi1 120.7(10) . . ? C6 C1 Bi1 119.2(8) . . ? C1 C2 C3 120.8(17) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 119.8(13) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.6(11) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.8(11) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.1(11) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C12 120.0 . . ? C8 C7 S1 117.7(3) . . ? C12 C7 S1 122.3(3) . . ? C7 C8 C9 120.0 . . ? C7 C8 C13 124.8 . . ? C9 C8 C13 115.1 . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.0 . . ? C9 C10 C14 121.0(6) . . ? C11 C10 C14 119.0(6) . . ? C10 C11 C12 120.0 . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 120.0 . . ? C11 C12 C15 115.4(5) . . ? C7 C12 C15 124.6(5) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 121.8(8) . . ? C21 C16 S2 119.6(7) . . ? C17 C16 S2 118.4(7) . . ? C18 C17 C16 118.1(9) . . ? C18 C17 C22 118.0(9) . . ? C16 C17 C22 123.8(8) . . ? C17 C18 C19 122.4(10) . . ? C17 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? C18 C19 C20 117.9(8) . . ? C18 C19 C23 120.8(9) . . ? C20 C19 C23 121.2(9) . . ? C19 C20 C21 122.8(9) . . ? C19 C20 H20 118.6 . . ? C21 C20 H20 118.6 . . ? C20 C21 C16 116.9(9) . . ? C20 C21 C24 116.4(8) . . ? C16 C21 C24 126.8(8) . . ? 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 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 1.065 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.134 # Attachment '- Compound 3.cif' data_jon94abs _database_code_depnum_ccdc_archive 'CCDC 775520' #TrackingRef '- Compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H25 Bi1 O4 S1' _chemical_formula_sum 'C22 H25 Bi1 O4 S1' _chemical_formula_weight 594.47 _chemical_absolute_configuration ad 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 10.8156(3) _cell_length_b 11.3881(3) _cell_length_c 16.6379(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2049.28(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 12996 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 30.51 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 8.731 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2502 _exptl_absorpt_correction_T_max 0.3838 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9802 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.25 _reflns_number_total 4126 _reflns_number_gt 3544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinoski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(9) _refine_ls_number_reflns 4126 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Bi1 Bi 0.08960(2) 0.826433(18) 0.50163(2) 0.01089(9) Uani 1 1 d . . . S1 S 0.29935(18) 0.60117(15) 0.44237(11) 0.0119(4) Uani 1 1 d . . . O1 O 0.2836(5) 0.7178(4) 0.4807(3) 0.0147(13) Uani 1 1 d . . . C1 C 0.2029(6) 0.9900(5) 0.4938(5) 0.0139(15) Uani 1 1 d . . . O2 O 0.4130(5) 0.5464(4) 0.4732(3) 0.0156(12) Uani 1 1 d . . . C2 C 0.1472(7) 1.0969(7) 0.4729(4) 0.0178(19) Uani 1 1 d . . . H2 H 0.0608 1.1001 0.4629 0.021 Uiso 1 1 calc R . . O3 O 0.1927(5) 0.5250(4) 0.4501(3) 0.0179(12) Uani 1 1 d . . . C3 C 0.2195(8) 1.1999(6) 0.4668(4) 0.0171(17) Uani 1 1 d . . . H3 H 0.1822 1.2723 0.4522 0.021 Uiso 1 1 calc R . . O4 O 0.5881(6) 0.5713(5) 0.3282(3) 0.0174(14) Uani 1 1 d . . . C4 C 0.3452(7) 1.1944(7) 0.4824(4) 0.0176(19) Uani 1 1 d . . . H4 H 0.3935 1.2640 0.4794 0.021 Uiso 1 1 calc R . . C5 C 0.4016(6) 1.0894(6) 0.5022(5) 0.0186(15) Uani 1 1 d . . . H5 H 0.4883 1.0861 0.5113 0.022 Uiso 1 1 calc R . . C6 C 0.3296(6) 0.9887(6) 0.5087(5) 0.0140(16) Uani 1 1 d . . . H6 H 0.3679 0.9169 0.5238 0.017 Uiso 1 1 calc R . . C7 C 0.0506(8) 0.8270(6) 0.3681(4) 0.0147(16) Uani 1 1 d . . . C8 C -0.0310(8) 0.7443(7) 0.3371(5) 0.0184(18) Uani 1 1 d . . . H8 H -0.0707 0.6899 0.3719 0.022 Uiso 1 1 calc R . . C9 C -0.0544(8) 0.7416(6) 0.2543(5) 0.0202(19) Uani 1 1 d . . . H9 H -0.1142 0.6887 0.2334 0.024 Uiso 1 1 calc R . . C10 C 0.0091(8) 0.8155(7) 0.2026(5) 0.0200(18) Uani 1 1 d . . . H10 H -0.0050 0.8113 0.1463 0.024 Uiso 1 1 calc R . . C11 C 0.0937(8) 0.8960(7) 0.2333(5) 0.0224(19) Uani 1 1 d . . . H11 H 0.1380 0.9465 0.1981 0.027 Uiso 1 1 calc R . . C12 C 0.1130(9) 0.9019(7) 0.3153(5) 0.016(2) Uani 1 1 d . . . H12 H 0.1696 0.9579 0.3362 0.019 Uiso 1 1 calc R . . C13 C 0.3242(7) 0.6360(6) 0.3393(4) 0.0123(16) Uani 1 1 d . . . H13B H 0.2444 0.6635 0.3170 0.015 Uiso 1 1 calc R . . H13A H 0.3818 0.7035 0.3374 0.015 Uiso 1 1 calc R . . C14 C 0.3740(7) 0.5431(7) 0.2829(4) 0.0120(17) Uani 1 1 d . . . C15 C 0.5155(8) 0.5352(6) 0.2787(4) 0.0155(17) Uani 1 1 d . . . C16 C 0.5455(7) 0.4782(6) 0.2003(4) 0.0161(17) Uani 1 1 d . . . H16B H 0.5928 0.4047 0.2085 0.019 Uiso 1 1 calc R . . H16A H 0.5939 0.5316 0.1654 0.019 Uiso 1 1 calc R . . C17 C 0.4180(7) 0.4526(6) 0.1636(4) 0.0124(16) Uani 1 1 d . . . H17 H 0.4182 0.4393 0.1042 0.015 Uiso 1 1 calc R . . C18 C 0.3604(8) 0.3540(6) 0.2127(5) 0.0202(19) Uani 1 1 d . . . H18B H 0.4188 0.2877 0.2190 0.024 Uiso 1 1 calc R . . H18A H 0.2837 0.3249 0.1870 0.024 Uiso 1 1 calc R . . C19 C 0.3320(8) 0.4123(6) 0.2954(4) 0.0129(17) Uani 1 1 d . . . H19A H 0.3797 0.3744 0.3391 0.016 Uiso 1 1 calc R . . H19B H 0.2428 0.4077 0.3082 0.016 Uiso 1 1 calc R . . C20 C 0.3418(8) 0.5615(6) 0.1919(4) 0.0161(19) Uani 1 1 d . . . C21 C 0.2037(8) 0.5534(7) 0.1726(5) 0.022(2) Uani 1 1 d . . . H21C H 0.1610 0.6222 0.1946 0.033 Uiso 1 1 calc R . . H21A H 0.1694 0.4819 0.1967 0.033 Uiso 1 1 calc R . . H21B H 0.1922 0.5509 0.1142 0.033 Uiso 1 1 calc R . . C22 C 0.3894(7) 0.6807(6) 0.1598(5) 0.0166(17) Uani 1 1 d . . . H22A H 0.3853 0.6810 0.1010 0.025 Uiso 1 1 calc R . . H22B H 0.4751 0.6924 0.1770 0.025 Uiso 1 1 calc R . . H22C H 0.3377 0.7442 0.1811 0.025 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 Bi1 0.00837(14) 0.01259(13) 0.01171(14) 0.00051(19) 0.0018(2) 0.00071(10) S1 0.0079(10) 0.0159(9) 0.0119(9) -0.0006(8) -0.0004(8) 0.0001(8) O1 0.012(3) 0.019(2) 0.013(3) -0.006(2) -0.006(2) 0.006(2) C1 0.016(4) 0.016(3) 0.010(4) 0.003(4) 0.007(4) 0.004(3) O2 0.010(3) 0.017(3) 0.020(3) 0.002(2) -0.003(2) -0.001(2) C2 0.007(4) 0.025(4) 0.021(4) -0.004(3) 0.002(3) 0.000(3) O3 0.008(3) 0.028(3) 0.018(3) 0.001(2) 0.002(2) -0.008(2) C3 0.014(4) 0.015(4) 0.023(4) 0.004(3) 0.008(3) -0.004(3) O4 0.015(3) 0.020(3) 0.018(3) 0.001(2) -0.004(3) -0.003(3) C4 0.015(4) 0.023(4) 0.016(5) -0.002(3) 0.002(3) -0.007(3) C5 0.013(4) 0.029(4) 0.014(3) -0.005(5) 0.005(6) -0.002(3) C6 0.014(4) 0.018(3) 0.010(4) 0.003(4) -0.005(4) 0.003(3) C7 0.009(4) 0.023(4) 0.011(4) 0.004(3) -0.004(3) 0.004(3) C8 0.015(4) 0.021(4) 0.019(4) 0.000(3) 0.002(4) -0.002(4) C9 0.017(5) 0.024(4) 0.020(4) -0.002(4) -0.002(4) -0.002(4) C10 0.014(5) 0.026(4) 0.021(4) 0.000(4) 0.001(3) 0.010(4) C11 0.020(5) 0.028(4) 0.019(4) 0.006(4) 0.005(4) 0.003(4) C12 0.014(5) 0.013(4) 0.020(4) -0.001(3) 0.000(4) 0.000(4) C13 0.012(4) 0.017(4) 0.008(4) 0.000(3) -0.002(3) 0.002(3) C14 0.011(4) 0.020(4) 0.006(4) -0.006(3) -0.005(3) 0.002(3) C15 0.018(5) 0.011(4) 0.018(4) 0.007(3) 0.002(4) 0.005(3) C16 0.014(4) 0.015(4) 0.020(4) -0.008(3) -0.002(3) 0.004(3) C17 0.007(4) 0.014(4) 0.016(4) -0.006(3) -0.001(3) 0.002(3) C18 0.014(4) 0.018(4) 0.028(5) -0.010(3) -0.001(4) 0.004(3) C19 0.012(5) 0.013(4) 0.013(4) 0.002(3) 0.002(3) 0.001(3) C20 0.024(5) 0.013(4) 0.011(4) -0.001(3) 0.002(4) 0.001(3) C21 0.017(5) 0.033(5) 0.015(4) -0.006(4) -0.008(4) 0.010(4) C22 0.017(5) 0.018(4) 0.014(4) 0.002(3) 0.000(3) 0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.233(6) . ? Bi1 C7 2.261(7) . ? Bi1 O2 2.433(5) 3_466 ? Bi1 O1 2.461(5) . ? S1 O3 1.449(5) . ? S1 O2 1.470(5) . ? S1 O1 1.483(5) . ? S1 C13 1.781(7) . ? C1 C6 1.393(9) . ? C1 C2 1.402(9) . ? O2 Bi1 2.433(5) 3_566 ? C2 C3 1.413(10) . ? C2 H2 0.9500 . ? C3 C4 1.386(11) . ? C3 H3 0.9500 . ? O4 C15 1.210(9) . ? C4 C5 1.382(10) . ? C4 H4 0.9500 . ? C5 C6 1.391(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.391(11) . ? C7 C12 1.398(11) . ? C8 C9 1.402(11) . ? C8 H8 0.9500 . ? C9 C10 1.386(11) . ? C9 H9 0.9500 . ? C10 C11 1.392(11) . ? C10 H10 0.9500 . ? C11 C12 1.382(11) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.514(10) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.535(11) . ? C14 C20 1.567(10) . ? C14 C19 1.571(10) . ? C15 C16 1.494(10) . ? C16 C17 1.536(10) . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? C17 C18 1.522(10) . ? C17 C20 1.562(10) . ? C17 H17 1.0000 . ? C18 C19 1.558(11) . ? C18 H18B 0.9900 . ? C18 H18A 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.531(11) . ? C20 C22 1.547(10) . ? C21 H21C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 _geom_angle_publ_flag C1 Bi1 C7 92.4(3) . . ? C1 Bi1 O2 86.8(2) . 3_466 ? C7 Bi1 O2 91.2(2) . 3_466 ? C1 Bi1 O1 86.8(2) . . ? C7 Bi1 O1 91.2(2) . . ? O2 Bi1 O1 173.22(16) 3_466 . ? O3 S1 O2 112.4(3) . . ? O3 S1 O1 114.0(3) . . ? O2 S1 O1 109.0(3) . . ? O3 S1 C13 109.9(3) . . ? O2 S1 C13 107.7(3) . . ? O1 S1 C13 103.4(3) . . ? S1 O1 Bi1 127.5(3) . . ? C6 C1 C2 118.4(6) . . ? C6 C1 Bi1 121.4(5) . . ? C2 C1 Bi1 120.2(5) . . ? S1 O2 Bi1 117.6(3) . 3_566 ? C1 C2 C3 120.1(7) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.4(8) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 121.1(7) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.0(7) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 121.9(7) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C8 C7 C12 119.1(7) . . ? C8 C7 Bi1 118.7(5) . . ? C12 C7 Bi1 122.0(6) . . ? C7 C8 C9 119.6(7) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.5(8) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.9(8) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.6(8) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 121.2(9) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C14 C13 S1 119.6(5) . . ? C14 C13 H13B 107.4 . . ? S1 C13 H13B 107.4 . . ? C14 C13 H13A 107.4 . . ? S1 C13 H13A 107.4 . . ? H13B C13 H13A 106.9 . . ? C13 C14 C15 115.0(6) . . ? C13 C14 C20 115.2(6) . . ? C15 C14 C20 100.7(6) . . ? C13 C14 C19 118.5(6) . . ? C15 C14 C19 103.8(6) . . ? C20 C14 C19 101.0(6) . . ? O4 C15 C16 127.0(8) . . ? O4 C15 C14 126.7(7) . . ? C16 C15 C14 106.3(7) . . ? C15 C16 C17 103.6(6) . . ? C15 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? C15 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? H16B C16 H16A 109.0 . . ? C18 C17 C16 107.1(6) . . ? C18 C17 C20 102.0(6) . . ? C16 C17 C20 101.7(6) . . ? C18 C17 H17 114.8 . . ? C16 C17 H17 114.8 . . ? C20 C17 H17 114.8 . . ? C17 C18 C19 103.9(6) . . ? C17 C18 H18B 111.0 . . ? C19 C18 H18B 111.0 . . ? C17 C18 H18A 111.0 . . ? C19 C18 H18A 111.0 . . ? H18B C18 H18A 109.0 . . ? C18 C19 C14 103.3(6) . . ? C18 C19 H19A 111.1 . . ? C14 C19 H19A 111.1 . . ? C18 C19 H19B 111.1 . . ? C14 C19 H19B 111.1 . . ? H19A C19 H19B 109.1 . . ? C21 C20 C22 107.8(7) . . ? C21 C20 C17 113.8(7) . . ? C22 C20 C17 114.7(6) . . ? C21 C20 C14 114.3(7) . . ? C22 C20 C14 112.2(6) . . ? C17 C20 C14 93.9(6) . . ? C20 C21 H21C 109.5 . . ? C20 C21 H21A 109.5 . . ? H21C C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? H21A C21 H21B 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 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.415 _refine_diff_density_min -1.945 _refine_diff_density_rms 0.187 # Attachment '- Compound 2.CIF' data_jon98 _database_code_depnum_ccdc_archive 'CCDC 775521' #TrackingRef '- Compound 2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 Bi O3 S' _chemical_formula_sum 'C21 H21 Bi O3 S' _chemical_formula_weight 562.42 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 11.7139(3) _cell_length_b 8.9011(3) _cell_length_c 19.1572(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.3340(10) _cell_angle_gamma 90.00 _cell_volume 1971.01(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 22416 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 30.01 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 9.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4091 _exptl_absorpt_correction_T_max 0.6122 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18715 _diffrn_reflns_av_R_equivalents 0.1054 _diffrn_reflns_av_sigmaI/netI 0.0986 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3864 _reflns_number_gt 2717 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_cell_refinement 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_data_reduction 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. C1 and C7 were constrained using the SIMU command to C2 and C8 respectively. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+39.3267P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3864 _refine_ls_number_parameters 238 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Bi1 Bi 0.77407(4) 0.88819(5) 0.21626(2) 0.01033(15) Uani 1 1 d . . . S1 S 0.5420(3) 0.6843(4) 0.25779(16) 0.0115(7) Uani 1 1 d . . . O1 O 0.6291(8) 0.6964(10) 0.2101(4) 0.015(2) Uani 1 1 d . . . O2 O 0.5409(8) 0.5279(11) 0.2834(5) 0.017(2) Uani 1 1 d . . . O3 O 0.5620(8) 0.7928(10) 0.3134(5) 0.021(2) Uani 1 1 d . . . C1 C 0.8818(11) 0.7535(15) 0.3004(6) 0.011(3) Uani 1 1 d U . . C2 C 0.8457(11) 0.7443(14) 0.3666(7) 0.014(3) Uani 1 1 d U . . H2 H 0.7747 0.7885 0.3737 0.017 Uiso 1 1 calc R . . C3 C 0.9157(12) 0.6692(16) 0.4221(7) 0.022(3) Uani 1 1 d . . . H3 H 0.8931 0.6661 0.4675 0.026 Uiso 1 1 calc R . . C4 C 1.0149(11) 0.6011(18) 0.4119(7) 0.023(3) Uani 1 1 d . . . H4 H 1.0586 0.5455 0.4493 0.028 Uiso 1 1 calc R . . C5 C 1.0535(12) 0.6118(19) 0.3471(7) 0.027(3) Uani 1 1 d . . . H5 H 1.1247 0.5670 0.3407 0.032 Uiso 1 1 calc R . . C6 C 0.9861(13) 0.6893(15) 0.2915(7) 0.019(3) Uani 1 1 d . . . H6 H 1.0122 0.6980 0.2473 0.023 Uiso 1 1 calc R . . C7 C 0.8139(10) 0.7645(14) 0.1225(6) 0.011(2) Uani 1 1 d U . . C8 C 0.8531(10) 0.6151(17) 0.1243(6) 0.017(3) Uani 1 1 d U . . H8 H 0.8696 0.5637 0.1683 0.020 Uiso 1 1 calc R . . C9 C 0.8678(12) 0.5421(16) 0.0622(7) 0.022(3) Uani 1 1 d . . . H9 H 0.8968 0.4423 0.0640 0.027 Uiso 1 1 calc R . . C10 C 0.8402(11) 0.6145(17) -0.0022(7) 0.020(3) Uani 1 1 d . . . H10 H 0.8494 0.5641 -0.0447 0.024 Uiso 1 1 calc R . . C11 C 0.7992(12) 0.7598(16) -0.0048(7) 0.019(3) Uani 1 1 d . . . H11 H 0.7798 0.8095 -0.0490 0.023 Uiso 1 1 calc R . . C12 C 0.7867(11) 0.8318(17) 0.0557(6) 0.019(3) Uani 1 1 d . . . H12 H 0.7583 0.9320 0.0528 0.022 Uiso 1 1 calc R . . C13 C 0.4050(10) 0.7234(14) 0.2048(7) 0.011(3) Uani 1 1 d . . . C14 C 0.3861(12) 0.6761(14) 0.1335(7) 0.015(3) Uani 1 1 d . . . C15 C 0.2839(12) 0.7232(15) 0.0911(7) 0.017(3) Uani 1 1 d . . . H15 H 0.2711 0.6945 0.0427 0.020 Uiso 1 1 calc R . . C16 C 0.2011(12) 0.8084(15) 0.1155(7) 0.019(3) Uani 1 1 d . . . C17 C 0.2189(12) 0.8429(15) 0.1882(7) 0.019(3) Uani 1 1 d . . . H17 H 0.1612 0.8972 0.2072 0.022 Uiso 1 1 calc R . . C18 C 0.3192(12) 0.7991(15) 0.2327(7) 0.016(3) Uani 1 1 d . . . C19 C 0.4664(13) 0.5794(17) 0.0981(7) 0.029(4) Uani 1 1 d . . . H19A H 0.4228 0.5333 0.0555 0.044 Uiso 1 1 calc R . . H19B H 0.4999 0.5005 0.1308 0.044 Uiso 1 1 calc R . . H19C H 0.5286 0.6418 0.0850 0.044 Uiso 1 1 calc R . . C20 C 0.0930(12) 0.8599(19) 0.0690(8) 0.032(4) Uani 1 1 d . . . H20A H 0.1119 0.8948 0.0237 0.048 Uiso 1 1 calc R . . H20B H 0.0582 0.9424 0.0921 0.048 Uiso 1 1 calc R . . H20C H 0.0381 0.7762 0.0607 0.048 Uiso 1 1 calc R . . C21 C 0.3294(13) 0.8466(18) 0.3101(7) 0.027(4) Uani 1 1 d . . . H21A H 0.3786 0.9359 0.3184 0.040 Uiso 1 1 calc R . . H21B H 0.3638 0.7646 0.3406 0.040 Uiso 1 1 calc R . . H21C H 0.2524 0.8696 0.3209 0.040 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 Bi1 0.0117(2) 0.0097(2) 0.0090(2) 0.0009(3) -0.00018(15) 0.0002(3) S1 0.0115(17) 0.0124(16) 0.0100(16) -0.0012(14) -0.0004(13) 0.0035(13) O1 0.014(5) 0.021(5) 0.009(4) 0.004(4) 0.004(4) 0.000(4) O2 0.017(5) 0.025(5) 0.010(5) 0.005(4) 0.005(4) -0.003(4) O3 0.014(5) 0.021(5) 0.026(5) -0.013(4) -0.009(4) 0.002(4) C1 0.010(6) 0.016(6) 0.008(6) 0.004(5) 0.000(5) 0.001(5) C2 0.011(6) 0.015(6) 0.014(6) 0.000(5) -0.004(5) -0.009(5) C3 0.025(8) 0.027(8) 0.011(7) 0.003(6) -0.002(6) -0.014(7) C4 0.017(7) 0.025(8) 0.023(7) 0.003(7) -0.008(6) 0.001(7) C5 0.016(7) 0.037(9) 0.027(8) 0.002(9) -0.001(6) 0.000(8) C6 0.032(9) 0.020(8) 0.006(6) -0.002(6) 0.007(6) -0.007(6) C7 0.007(6) 0.018(6) 0.010(5) -0.001(5) 0.007(5) 0.001(5) C8 0.017(6) 0.021(6) 0.014(5) 0.007(6) 0.003(4) 0.007(6) C9 0.026(8) 0.020(7) 0.020(7) -0.005(6) -0.001(6) 0.003(7) C10 0.027(8) 0.021(7) 0.011(6) 0.002(7) 0.002(5) -0.010(7) C11 0.018(8) 0.029(8) 0.008(6) 0.004(6) -0.006(5) 0.004(6) C12 0.014(7) 0.029(8) 0.011(6) 0.005(6) -0.005(5) 0.005(6) C13 0.004(6) 0.012(6) 0.018(7) 0.001(6) -0.002(5) -0.001(5) C14 0.018(7) 0.009(6) 0.016(7) -0.005(6) -0.007(6) 0.004(6) C15 0.026(8) 0.014(7) 0.010(6) 0.002(6) 0.001(6) 0.004(6) C16 0.018(8) 0.016(7) 0.022(8) -0.002(6) 0.001(6) -0.008(6) C17 0.014(7) 0.020(8) 0.022(7) 0.000(6) 0.002(6) 0.002(6) C18 0.017(7) 0.016(7) 0.015(7) 0.000(6) 0.003(5) -0.001(6) C19 0.038(9) 0.033(10) 0.013(7) -0.008(7) -0.007(6) 0.013(7) C20 0.011(7) 0.044(11) 0.036(9) 0.010(8) -0.009(6) -0.009(7) C21 0.019(8) 0.039(10) 0.024(8) -0.010(7) 0.011(6) -0.001(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C7 2.220(12) . ? Bi1 C1 2.229(12) . ? Bi1 O1 2.398(9) . ? Bi1 O2 2.498(9) 2_655 ? S1 O3 1.428(9) . ? S1 O2 1.477(10) . ? S1 O1 1.479(9) . ? S1 C13 1.789(12) . ? O2 Bi1 2.498(9) 2_645 ? C1 C6 1.385(19) . ? C1 C2 1.401(17) . ? C2 C3 1.403(18) . ? C2 H2 0.9500 . ? C3 C4 1.35(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(19) . ? C4 H4 0.9500 . ? C5 C6 1.401(19) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.401(17) . ? C7 C8 1.406(19) . ? C8 C9 1.391(18) . ? C8 H8 0.9500 . ? C9 C10 1.384(18) . ? C9 H9 0.9500 . ? C10 C11 1.38(2) . ? C10 H10 0.9500 . ? C11 C12 1.353(18) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.387(18) . ? C13 C14 1.412(17) . ? C14 C15 1.397(18) . ? C14 C19 1.515(19) . ? C15 C16 1.373(19) . ? C15 H15 0.9500 . ? C16 C17 1.407(19) . ? C16 C20 1.498(19) . ? C17 C18 1.392(18) . ? C17 H17 0.9500 . ? C18 C21 1.527(18) . ? 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 . ? 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 _geom_angle_publ_flag C7 Bi1 C1 98.6(5) . . ? C7 Bi1 O1 81.2(4) . . ? C1 Bi1 O1 88.0(4) . . ? C7 Bi1 O2 87.3(4) . 2_655 ? C1 Bi1 O2 82.9(4) . 2_655 ? O1 Bi1 O2 164.2(3) . 2_655 ? O3 S1 O2 113.5(6) . . ? O3 S1 O1 111.4(6) . . ? O2 S1 O1 108.5(5) . . ? O3 S1 C13 108.3(6) . . ? O2 S1 C13 108.4(6) . . ? O1 S1 C13 106.3(6) . . ? S1 O1 Bi1 125.1(5) . . ? S1 O2 Bi1 114.6(5) . 2_645 ? C6 C1 C2 119.3(12) . . ? C6 C1 Bi1 122.7(9) . . ? C2 C1 Bi1 117.8(9) . . ? C1 C2 C3 119.3(13) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 120.9(13) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.7(13) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.2(14) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 120.6(12) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C12 C7 C8 116.9(12) . . ? C12 C7 Bi1 118.7(10) . . ? C8 C7 Bi1 124.0(9) . . ? C9 C8 C7 120.4(12) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.1(13) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.9(13) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.0(13) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 122.6(13) . . ? C11 C12 H12 118.7 . . ? C7 C12 H12 118.7 . . ? C18 C13 C14 120.6(12) . . ? C18 C13 S1 121.0(10) . . ? C14 C13 S1 118.4(9) . . ? C15 C14 C13 117.3(12) . . ? C15 C14 C19 116.4(12) . . ? C13 C14 C19 126.3(11) . . ? C16 C15 C14 123.6(13) . . ? C16 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C15 C16 C17 117.3(13) . . ? C15 C16 C20 122.9(13) . . ? C17 C16 C20 119.8(13) . . ? C18 C17 C16 121.3(13) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C13 119.5(12) . . ? C17 C18 C21 116.3(12) . . ? C13 C18 C21 124.1(12) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 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 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.838 _refine_diff_density_min -2.984 _refine_diff_density_rms 0.309