# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Shuangfeng Yin' _publ_contact_author_address # Address of author for correspondence ; College of Chemistryand Chemical Engineering, Hunan University, Changsha,410082, China. ; _publ_contact_author_email sfyin73@yahoo.com.cn _publ_contact_author_fax +86-731-88821310 _publ_contact_author_phone +86-731-88821310 _publ_contact_letter ; Please consider this CIF for publication. I certify that this contibution is the original work of those listed as authors; that it has not been published before (in any language or medium) and is not being considered for publication elsewhere; that all authors concur with and are aware of the submission; that all workers involved in the study are listed as authors or given proper credit in the acknowledgements; that I have obtained permission for and acknowledged the source of any excerpts from other copyright works; and that to the best of my knowledge the paper contains no statements which are libellous, unlawful or in any way actionable. All coauthors have made significant scientific contributions to the work reported, including the ideas and their execution, and share responsibility and accountability for the results. ; _publ_section_title ; Effect of butterfly-shaped sulfur-bridged ligand and counter anions on the catalytic activity and diastereoselectivity of organobismuth complexes ; _publ_section_comment ; The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF. For related literature, see [type here to add references to related literature]. ; # Attachment '- S+Bi+C4-compound 4 (CCDC791966).cif' #============================================================================== #TrackingRef '- S+Bi+C4-compound 4 (CCDC791966).cif' _publ_manuscript_text # Used for convenience to store draft or replaced versions # of the abstract, comment etc. # Its contents will not be output ; ? ; loop_ _publ_author_name 'Renhua Qiu' 'Shuangfeng Yin' 'Xingxing Song' 'Zhengong Meng' ; Yimiao Qiu ; 'Nianyuan Tan' 'Xinhua Xu' 'Shenglian Luo' 'Feng-Rong Dai' ; Chak-tong Au ; 'Wai-Yeung (Raymond) Wong' data_1 _database_code_depnum_ccdc_archive 'CCDC 724767' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Bi Cl S' _chemical_formula_weight 456.73 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9590(6) _cell_length_b 9.0096(6) _cell_length_c 34.274(3) _cell_angle_alpha 93.165(2) _cell_angle_beta 93.3060(10) _cell_angle_gamma 90.1870(10) _cell_volume 2757.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 13.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3954 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13143 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9349 _reflns_number_gt 7386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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^)+(0.0998P)^2^+15.6265P] 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 9349 _refine_ls_number_parameters 613 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.19188(6) 0.27426(6) 0.372892(17) 0.03933(17) Uani 1 1 d . . . Bi2 Bi 0.72489(6) 0.30590(6) 0.128965(17) 0.03952(16) Uani 1 1 d . . . Bi3 Bi 0.22441(6) 0.24570(6) 0.128517(17) 0.03991(17) Uani 1 1 d . . . Bi4 Bi 0.25444(6) 0.77448(6) 0.371640(18) 0.04192(17) Uani 1 1 d . . . C1 C 0.0535(17) 0.3892(17) 0.3254(4) 0.044(4) Uani 1 1 d . . . C2 C 0.122(2) 0.4742(19) 0.3008(5) 0.057(4) Uani 1 1 d . . . H2A H 0.2253 0.4862 0.3032 0.069 Uiso 1 1 calc R . . C3 C 0.039(3) 0.544(3) 0.2717(6) 0.094(8) Uani 1 1 d . . . H3A H 0.0872 0.6019 0.2545 0.113 Uiso 1 1 calc R . . C4 C -0.117(4) 0.529(3) 0.2681(7) 0.102(10) Uani 1 1 d . . . H4A H -0.1744 0.5786 0.2495 0.123 Uiso 1 1 calc R . . C5 C -0.185(2) 0.435(3) 0.2934(6) 0.076(6) Uani 1 1 d . . . H5A H -0.2876 0.4183 0.2907 0.091 Uiso 1 1 calc R . . C6 C -0.0989(17) 0.3676(18) 0.3225(5) 0.051(4) Uani 1 1 d . . . C7 C -0.1850(18) 0.262(2) 0.3472(6) 0.070(6) Uani 1 1 d . . . H7A H -0.1802 0.1614 0.3359 0.084 Uiso 1 1 calc R . . H7B H -0.2892 0.2910 0.3471 0.084 Uiso 1 1 calc R . . C8 C -0.099(2) 0.4679(18) 0.4119(5) 0.058(4) Uani 1 1 d . . . H8A H -0.1110 0.5247 0.3887 0.069 Uiso 1 1 calc R . . H8B H -0.1820 0.4920 0.4282 0.069 Uiso 1 1 calc R . . C9 C 0.039(2) 0.5096(18) 0.4331(5) 0.058(5) Uani 1 1 d . . . C10 C 0.037(3) 0.609(2) 0.4650(6) 0.074(6) Uani 1 1 d . . . H10A H -0.0534 0.6463 0.4731 0.088 Uiso 1 1 calc R . . C11 C 0.171(3) 0.653(2) 0.4854(7) 0.087(8) Uani 1 1 d . . . H11A H 0.1672 0.7231 0.5062 0.105 Uiso 1 1 calc R . . C12 C 0.311(3) 0.596(2) 0.4760(6) 0.086(7) Uani 1 1 d . . . H12A H 0.3986 0.6248 0.4902 0.103 Uiso 1 1 calc R . . C13 C 0.310(3) 0.4936(19) 0.4441(5) 0.064(5) Uani 1 1 d . . . H13A H 0.4002 0.4525 0.4372 0.077 Uiso 1 1 calc R . . C14 C 0.1792(18) 0.4488(16) 0.4218(4) 0.042(3) Uani 1 1 d . . . C15 C 0.6033(17) 0.4400(15) 0.1746(4) 0.041(3) Uani 1 1 d . . . C16 C 0.5169(18) 0.375(2) 0.2017(5) 0.056(4) Uani 1 1 d . . . H16A H 0.5060 0.2725 0.2005 0.067 Uiso 1 1 calc R . . C17 C 0.449(2) 0.457(3) 0.2296(6) 0.079(6) Uani 1 1 d . . . H17A H 0.3931 0.4097 0.2474 0.095 Uiso 1 1 calc R . . C18 C 0.461(2) 0.611(3) 0.2319(7) 0.081(7) Uani 1 1 d . . . H18A H 0.4096 0.6667 0.2504 0.097 Uiso 1 1 calc R . . C19 C 0.550(2) 0.683(2) 0.2062(5) 0.069(6) Uani 1 1 d . . . H19A H 0.5573 0.7857 0.2077 0.082 Uiso 1 1 calc R . . C20 C 0.6275(17) 0.5987(16) 0.1782(5) 0.044(4) Uani 1 1 d . . . C21 C 0.727(2) 0.6749(19) 0.1542(5) 0.063(5) Uani 1 1 d . . . H21A H 0.8276 0.6707 0.1661 0.076 Uiso 1 1 calc R . . H21B H 0.6986 0.7787 0.1541 0.076 Uiso 1 1 calc R . . C22 C 0.5329(19) 0.599(2) 0.0889(5) 0.063(5) Uani 1 1 d . . . H22A H 0.4747 0.6089 0.1119 0.075 Uiso 1 1 calc R . . H22B H 0.5094 0.6823 0.0729 0.075 Uiso 1 1 calc R . . C23 C 0.4927(18) 0.454(2) 0.0658(5) 0.053(4) Uani 1 1 d . . . C24 C 0.390(2) 0.453(3) 0.0336(6) 0.075(6) Uani 1 1 d . . . H24A H 0.3475 0.5412 0.0257 0.090 Uiso 1 1 calc R . . C25 C 0.352(2) 0.320(3) 0.0135(6) 0.084(7) Uani 1 1 d . . . H25A H 0.2855 0.3196 -0.0084 0.100 Uiso 1 1 calc R . . C26 C 0.410(2) 0.188(3) 0.0254(5) 0.065(5) Uani 1 1 d . . . H26A H 0.3836 0.0993 0.0116 0.078 Uiso 1 1 calc R . . C27 C 0.507(2) 0.188(2) 0.0575(5) 0.061(5) Uani 1 1 d . . . H27A H 0.5458 0.0983 0.0654 0.074 Uiso 1 1 calc R . . C28 C 0.5492(14) 0.3168(17) 0.0787(4) 0.040(3) Uani 1 1 d . . . C29 C 0.0452(17) 0.219(2) 0.0783(5) 0.050(4) Uani 1 1 d . . . C30 C 0.0101(17) 0.343(2) 0.0596(5) 0.061(5) Uani 1 1 d . . . H30A H 0.0507 0.4354 0.0680 0.073 Uiso 1 1 calc R . . C31 C -0.094(2) 0.325(3) 0.0255(6) 0.073(6) Uani 1 1 d . . . H31A H -0.1256 0.4072 0.0119 0.088 Uiso 1 1 calc R . . C32 C -0.147(2) 0.183(4) 0.0137(6) 0.090(8) Uani 1 1 d . . . H32A H -0.2119 0.1713 -0.0085 0.108 Uiso 1 1 calc R . . C33 C -0.107(2) 0.063(3) 0.0333(6) 0.072(6) Uani 1 1 d . . . H33A H -0.1458 -0.0301 0.0250 0.086 Uiso 1 1 calc R . . C34 C -0.0093(16) 0.078(2) 0.0654(5) 0.055(4) Uani 1 1 d . . . C35 C 0.030(2) -0.062(2) 0.0860(5) 0.061(5) Uani 1 1 d . . . H35A H 0.0059 -0.1482 0.0687 0.073 Uiso 1 1 calc R . . H35B H -0.0280 -0.0673 0.1090 0.073 Uiso 1 1 calc R . . C36 C 0.236(2) -0.1203(18) 0.1504(5) 0.056(4) Uani 1 1 d . . . H36A H 0.2081 -0.2245 0.1496 0.067 Uiso 1 1 calc R . . H36B H 0.3375 -0.1110 0.1619 0.067 Uiso 1 1 calc R . . C37 C 0.1317(16) -0.0316(16) 0.1761(4) 0.040(3) Uani 1 1 d . . . C38 C 0.0647(19) -0.109(2) 0.2046(5) 0.058(4) Uani 1 1 d . . . H38A H 0.0795 -0.2103 0.2061 0.069 Uiso 1 1 calc R . . C39 C -0.025(2) -0.032(2) 0.2311(6) 0.070(5) Uani 1 1 d . . . H39A H -0.0738 -0.0842 0.2493 0.084 Uiso 1 1 calc R . . C40 C -0.042(2) 0.112(2) 0.2305(5) 0.065(5) Uani 1 1 d . . . H40A H -0.0961 0.1614 0.2496 0.078 Uiso 1 1 calc R . . C41 C 0.022(2) 0.193(2) 0.2011(5) 0.058(5) Uani 1 1 d . . . H41A H 0.0083 0.2954 0.2006 0.070 Uiso 1 1 calc R . . C42 C 0.1039(15) 0.1187(16) 0.1730(5) 0.043(3) Uani 1 1 d . . . C43 C 0.2873(19) 0.9474(16) 0.4205(5) 0.048(4) Uani 1 1 d . . . C44 C 0.164(2) 0.9913(16) 0.4425(5) 0.056(4) Uani 1 1 d . . . H44A H 0.0697 0.9517 0.4359 0.067 Uiso 1 1 calc R . . C45 C 0.187(3) 1.096(2) 0.4745(6) 0.087(8) Uani 1 1 d . . . H45A H 0.1038 1.1273 0.4877 0.105 Uiso 1 1 calc R . . C46 C 0.322(3) 1.153(2) 0.4872(7) 0.086(7) Uani 1 1 d . . . H46A H 0.3331 1.2181 0.5092 0.103 Uiso 1 1 calc R . . C47 C 0.445(3) 1.109(2) 0.4659(6) 0.072(6) Uani 1 1 d . . . H47A H 0.5390 1.1497 0.4732 0.087 Uiso 1 1 calc R . . C48 C 0.431(2) 1.0042(17) 0.4337(5) 0.056(4) Uani 1 1 d . . . C49 C 0.564(2) 0.962(2) 0.4117(5) 0.062(5) Uani 1 1 d . . . H49A H 0.6540 0.9868 0.4278 0.074 Uiso 1 1 calc R . . H49B H 0.5648 1.0185 0.3884 0.074 Uiso 1 1 calc R . . C50 C 0.6130(18) 0.7637(18) 0.3466(6) 0.058(4) Uani 1 1 d . . . H50A H 0.7184 0.7878 0.3460 0.069 Uiso 1 1 calc R . . H50B H 0.5978 0.6640 0.3348 0.069 Uiso 1 1 calc R . . C51 C 0.5257(18) 0.8689(16) 0.3230(5) 0.047(4) Uani 1 1 d . . . C52 C 0.603(2) 0.942(2) 0.2932(5) 0.056(4) Uani 1 1 d . . . H52A H 0.7048 0.9281 0.2912 0.067 Uiso 1 1 calc R . . C53 C 0.527(2) 1.031(2) 0.2680(5) 0.064(5) Uani 1 1 d . . . H53A H 0.5763 1.0810 0.2494 0.077 Uiso 1 1 calc R . . C54 C 0.382(3) 1.045(2) 0.2709(5) 0.069(6) Uani 1 1 d . . . H54A H 0.3299 1.0995 0.2524 0.083 Uiso 1 1 calc R . . C55 C 0.3010(18) 0.9836(18) 0.2998(5) 0.049(4) Uani 1 1 d . . . H55A H 0.1999 1.0040 0.3017 0.059 Uiso 1 1 calc R . . C56 C 0.3757(16) 0.8904(15) 0.3260(4) 0.040(3) Uani 1 1 d . . . Cl1 Cl 0.4399(4) 0.4017(5) 0.35361(16) 0.0695(13) Uani 1 1 d . . . Cl2 Cl 0.5964(5) 0.0587(4) 0.14839(15) 0.0638(12) Uani 1 1 d . . . Cl3 Cl 0.0927(6) 0.4982(4) 0.15039(15) 0.0662(12) Uani 1 1 d . . . Cl4 Cl -0.0008(4) 0.9048(6) 0.35104(16) 0.0690(13) Uani 1 1 d . . . S1 S -0.1062(5) 0.2685(5) 0.39728(15) 0.0593(11) Uani 1 1 d . . . S2 S 0.7300(5) 0.6018(5) 0.10357(14) 0.0545(10) Uani 1 1 d . . . S3 S 0.2327(5) -0.0592(4) 0.10079(13) 0.0520(10) Uani 1 1 d . . . S4 S 0.5629(5) 0.7657(5) 0.39761(14) 0.0537(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0381(3) 0.0310(3) 0.0493(4) 0.0048(2) 0.0026(2) 0.0077(2) Bi2 0.0336(3) 0.0336(3) 0.0515(4) 0.0032(2) 0.0026(2) 0.0060(2) Bi3 0.0337(3) 0.0346(3) 0.0515(4) 0.0056(2) 0.0011(2) -0.0045(2) Bi4 0.0383(3) 0.0318(3) 0.0559(4) 0.0025(2) 0.0051(2) -0.0044(2) C1 0.049(8) 0.054(9) 0.029(8) 0.005(7) -0.001(6) 0.025(7) C2 0.078(12) 0.051(10) 0.042(10) -0.006(8) 0.005(9) 0.004(9) C3 0.14(2) 0.094(17) 0.047(13) 0.026(12) 0.008(14) 0.031(16) C4 0.14(2) 0.104(19) 0.056(15) -0.004(13) -0.041(15) 0.062(18) C5 0.069(13) 0.085(15) 0.066(14) -0.028(12) -0.024(10) 0.024(11) C6 0.038(8) 0.049(9) 0.063(11) -0.016(8) -0.008(7) 0.011(7) C7 0.036(9) 0.084(13) 0.084(14) -0.023(11) -0.022(8) 0.009(9) C8 0.069(11) 0.050(10) 0.055(11) 0.001(8) 0.016(9) 0.015(8) C9 0.072(12) 0.042(9) 0.063(12) 0.004(8) 0.029(9) -0.002(8) C10 0.116(18) 0.039(10) 0.070(14) 0.010(9) 0.037(13) 0.003(11) C11 0.14(2) 0.032(10) 0.097(18) -0.009(10) 0.047(17) -0.013(12) C12 0.14(2) 0.063(13) 0.056(13) 0.021(11) -0.026(13) -0.020(13) C13 0.101(15) 0.044(9) 0.048(11) -0.001(8) 0.008(10) -0.011(9) C14 0.064(10) 0.040(8) 0.024(8) 0.007(6) -0.004(7) 0.005(7) C15 0.052(8) 0.030(7) 0.039(9) -0.003(6) 0.002(7) -0.005(6) C16 0.048(9) 0.074(12) 0.047(10) 0.007(9) 0.006(7) 0.009(8) C17 0.078(14) 0.092(16) 0.067(14) -0.026(12) 0.015(11) 0.001(12) C18 0.060(12) 0.103(17) 0.077(15) -0.037(13) 0.011(11) 0.011(11) C19 0.091(14) 0.068(12) 0.044(11) -0.013(9) -0.015(10) 0.045(11) C20 0.050(9) 0.031(7) 0.050(10) -0.001(7) -0.014(7) 0.016(6) C21 0.071(12) 0.044(9) 0.071(13) -0.009(9) -0.020(9) 0.007(8) C22 0.058(10) 0.069(12) 0.063(12) 0.027(10) 0.002(9) 0.023(9) C23 0.049(9) 0.076(12) 0.036(9) 0.018(8) 0.002(7) 0.000(8) C24 0.062(11) 0.107(17) 0.061(13) 0.040(13) -0.003(10) -0.002(11) C25 0.061(12) 0.14(2) 0.050(12) 0.018(14) -0.021(9) -0.033(13) C26 0.051(10) 0.096(15) 0.046(11) -0.003(10) 0.001(8) -0.011(10) C27 0.059(10) 0.087(14) 0.039(10) -0.003(9) 0.015(8) 0.003(10) C28 0.028(7) 0.052(9) 0.040(9) 0.014(7) -0.004(6) 0.013(6) C29 0.044(8) 0.068(11) 0.038(9) 0.008(8) 0.000(7) -0.001(8) C30 0.036(8) 0.091(14) 0.061(12) 0.027(10) 0.008(8) 0.018(8) C31 0.059(11) 0.110(18) 0.054(12) 0.016(12) 0.011(9) 0.017(12) C32 0.059(12) 0.16(3) 0.045(12) 0.005(15) -0.007(9) 0.010(15) C33 0.056(11) 0.094(15) 0.062(13) -0.025(12) 0.010(9) 0.008(11) C34 0.027(7) 0.076(12) 0.058(11) -0.023(9) 0.010(7) -0.004(7) C35 0.066(11) 0.060(11) 0.056(12) -0.001(9) 0.003(9) -0.010(9) C36 0.065(10) 0.042(9) 0.062(12) 0.013(8) 0.005(8) 0.011(8) C37 0.040(7) 0.036(7) 0.043(9) 0.002(6) -0.007(6) -0.009(6) C38 0.061(10) 0.053(10) 0.061(12) 0.021(9) 0.003(8) -0.014(8) C39 0.083(13) 0.078(14) 0.053(12) 0.012(10) 0.026(10) -0.019(11) C40 0.077(12) 0.079(13) 0.040(10) -0.003(9) 0.009(9) 0.025(10) C41 0.072(11) 0.054(10) 0.047(10) -0.019(8) 0.012(8) -0.020(9) C42 0.030(7) 0.040(8) 0.059(10) -0.002(7) 0.004(6) 0.003(6) C43 0.061(10) 0.037(8) 0.048(10) 0.017(7) 0.006(8) 0.007(7) C44 0.069(11) 0.032(8) 0.068(12) 0.010(8) 0.016(9) 0.005(7) C45 0.16(3) 0.057(12) 0.040(11) -0.002(10) 0.006(13) 0.043(15) C46 0.13(2) 0.062(13) 0.064(15) -0.006(11) -0.026(14) 0.019(13) C47 0.107(16) 0.045(10) 0.059(13) -0.007(9) -0.026(11) 0.002(10) C48 0.080(12) 0.033(8) 0.056(11) 0.013(8) -0.012(9) -0.003(8) C49 0.073(12) 0.058(11) 0.053(11) 0.014(9) -0.024(9) -0.017(9) C50 0.043(9) 0.044(9) 0.084(13) -0.010(9) 0.009(8) 0.000(7) C51 0.057(9) 0.032(7) 0.052(10) -0.010(7) 0.006(7) -0.031(7) C52 0.052(9) 0.067(11) 0.050(11) 0.002(9) 0.004(8) -0.020(8) C53 0.070(12) 0.077(13) 0.044(11) -0.007(9) 0.012(9) -0.022(10) C54 0.111(17) 0.063(12) 0.033(10) 0.018(9) -0.027(10) -0.003(11) C55 0.047(9) 0.056(10) 0.044(10) -0.004(8) 0.001(7) -0.007(7) C56 0.048(8) 0.031(7) 0.040(9) -0.005(6) -0.008(6) 0.000(6) Cl1 0.037(2) 0.063(3) 0.110(4) -0.003(3) 0.022(2) 0.0002(18) Cl2 0.070(3) 0.0300(19) 0.092(4) 0.015(2) -0.001(2) 0.0010(18) Cl3 0.078(3) 0.0282(19) 0.089(4) -0.007(2) -0.013(2) 0.0050(18) Cl4 0.0286(18) 0.078(3) 0.099(4) -0.003(3) -0.002(2) 0.0015(18) S1 0.055(2) 0.053(2) 0.073(3) 0.011(2) 0.019(2) -0.0001(19) S2 0.051(2) 0.048(2) 0.066(3) 0.013(2) 0.004(2) -0.0028(18) S3 0.053(2) 0.044(2) 0.060(3) -0.0054(19) 0.0146(19) 0.0020(17) S4 0.053(2) 0.046(2) 0.062(3) 0.014(2) -0.0084(19) 0.0044(18) _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 C14 2.242(15) . ? Bi1 C1 2.285(14) . ? Bi1 Cl1 2.632(4) . ? Bi1 S1 2.845(4) . ? Bi2 C15 2.256(14) . ? Bi2 C28 2.273(14) . ? Bi2 Cl2 2.638(4) . ? Bi2 S2 2.851(4) . ? Bi3 C42 2.275(15) . ? Bi3 C29 2.287(16) . ? Bi3 Cl3 2.657(4) . ? Bi3 S3 2.860(4) . ? Bi4 C43 2.229(17) . ? Bi4 C56 2.255(15) . ? Bi4 Cl4 2.651(4) . ? Bi4 S4 2.857(4) . ? C1 C2 1.34(2) . ? C1 C6 1.38(2) . ? C2 C3 1.39(3) . ? C2 H2A 0.9300 . ? C3 C4 1.41(4) . ? C3 H3A 0.9300 . ? C4 C5 1.40(4) . ? C4 H4A 0.9300 . ? C5 C6 1.39(3) . ? C5 H5A 0.9300 . ? C6 C7 1.54(3) . ? C7 S1 1.815(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.44(3) . ? C8 S1 1.838(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.37(3) . ? C9 C14 1.44(2) . ? C10 C11 1.40(3) . ? C10 H10A 0.9300 . ? C11 C12 1.40(3) . ? C11 H11A 0.9300 . ? C12 C13 1.39(3) . ? C12 H12A 0.9300 . ? C13 C14 1.41(3) . ? C13 H13A 0.9300 . ? C15 C16 1.39(2) . ? C15 C20 1.44(2) . ? C16 C17 1.35(2) . ? C16 H16A 0.9300 . ? C17 C18 1.39(3) . ? C17 H17A 0.9300 . ? C18 C19 1.40(3) . ? C18 H18A 0.9300 . ? C19 C20 1.41(2) . ? C19 H19A 0.9300 . ? C20 C21 1.44(2) . ? C21 S2 1.822(19) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.52(3) . ? C22 S2 1.808(18) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.40(3) . ? C23 C28 1.42(2) . ? C24 C25 1.38(3) . ? C24 H24A 0.9300 . ? C25 C26 1.37(3) . ? C25 H25A 0.9300 . ? C26 C27 1.36(3) . ? C26 H26A 0.9300 . ? C27 C28 1.37(2) . ? C27 H27A 0.9300 . ? C29 C30 1.35(2) . ? C29 C34 1.39(2) . ? C30 C31 1.45(3) . ? C30 H30A 0.9300 . ? C31 C32 1.39(3) . ? C31 H31A 0.9300 . ? C32 C33 1.35(3) . ? C32 H32A 0.9300 . ? C33 C34 1.37(3) . ? C33 H33A 0.9300 . ? C34 C35 1.51(3) . ? C35 S3 1.859(19) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.52(2) . ? C36 S3 1.813(17) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C42 1.39(2) . ? C37 C38 1.39(2) . ? C38 C39 1.40(3) . ? C38 H38A 0.9300 . ? C39 C40 1.30(3) . ? C39 H39A 0.9300 . ? C40 C41 1.42(2) . ? C40 H40A 0.9300 . ? C41 C42 1.39(2) . ? C41 H41A 0.9300 . ? C43 C44 1.42(2) . ? C43 C48 1.42(2) . ? C44 C45 1.41(3) . ? C44 H44A 0.9300 . ? C45 C46 1.35(4) . ? C45 H45A 0.9300 . ? C46 C47 1.40(3) . ? C46 H46A 0.9300 . ? C47 C48 1.41(3) . ? C47 H47A 0.9300 . ? C48 C49 1.49(3) . ? C49 S4 1.807(19) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.48(2) . ? C50 S4 1.829(19) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C56 1.37(2) . ? C51 C52 1.45(2) . ? C52 C53 1.37(3) . ? C52 H52A 0.9300 . ? C53 C54 1.31(3) . ? C53 H53A 0.9300 . ? C54 C55 1.40(2) . ? C54 H54A 0.9300 . ? C55 C56 1.41(2) . ? C55 H55A 0.9300 . ? 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 C14 Bi1 C1 98.9(5) . . ? C14 Bi1 Cl1 88.4(4) . . ? C1 Bi1 Cl1 91.8(4) . . ? C14 Bi1 S1 73.3(4) . . ? C1 Bi1 S1 75.2(4) . . ? Cl1 Bi1 S1 155.23(13) . . ? C15 Bi2 C28 98.0(5) . . ? C15 Bi2 Cl2 91.0(4) . . ? C28 Bi2 Cl2 88.4(4) . . ? C15 Bi2 S2 75.7(4) . . ? C28 Bi2 S2 73.1(4) . . ? Cl2 Bi2 S2 155.12(13) . . ? C42 Bi3 C29 97.4(5) . . ? C42 Bi3 Cl3 91.7(4) . . ? C29 Bi3 Cl3 87.8(4) . . ? C42 Bi3 S3 74.8(4) . . ? C29 Bi3 S3 73.8(5) . . ? Cl3 Bi3 S3 155.18(14) . . ? C43 Bi4 C56 98.2(5) . . ? C43 Bi4 Cl4 88.4(4) . . ? C56 Bi4 Cl4 91.6(4) . . ? C43 Bi4 S4 73.4(4) . . ? C56 Bi4 S4 75.1(4) . . ? Cl4 Bi4 S4 155.34(14) . . ? C2 C1 C6 121.5(16) . . ? C2 C1 Bi1 119.7(13) . . ? C6 C1 Bi1 118.8(12) . . ? C1 C2 C3 120(2) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 120(2) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 118(2) . . ? C5 C4 H4A 121.0 . . ? C3 C4 H4A 121.0 . . ? C6 C5 C4 120(2) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C1 C6 C5 119.6(18) . . ? C1 C6 C7 124.9(15) . . ? C5 C6 C7 115.3(16) . . ? C6 C7 S1 110.7(12) . . ? C6 C7 H7A 109.5 . . ? S1 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 S1 112.0(12) . . ? C9 C8 H8A 109.2 . . ? S1 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? S1 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 119.5(18) . . ? C10 C9 C14 119(2) . . ? C8 C9 C14 121.3(16) . . ? C9 C10 C11 120(2) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C12 123(2) . . ? C10 C11 H11A 118.4 . . ? C12 C11 H11A 118.4 . . ? C13 C12 C11 116(2) . . ? C13 C12 H12A 122.1 . . ? C11 C12 H12A 122.1 . . ? C12 C13 C14 124(2) . . ? C12 C13 H13A 118.2 . . ? C14 C13 H13A 118.2 . . ? C13 C14 C9 118.2(15) . . ? C13 C14 Bi1 119.8(12) . . ? C9 C14 Bi1 121.8(12) . . ? C16 C15 C20 118.5(14) . . ? C16 C15 Bi2 122.9(11) . . ? C20 C15 Bi2 118.3(10) . . ? C17 C16 C15 122.2(19) . . ? C17 C16 H16A 118.9 . . ? C15 C16 H16A 118.9 . . ? C16 C17 C18 121(2) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C17 C18 C19 120.0(18) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 120.2(19) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C19 C20 C15 118.2(16) . . ? C19 C20 C21 118.8(16) . . ? C15 C20 C21 123.0(14) . . ? C20 C21 S2 115.4(12) . . ? C20 C21 H21A 108.4 . . ? S2 C21 H21A 108.4 . . ? C20 C21 H21B 108.4 . . ? S2 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? C23 C22 S2 109.7(11) . . ? C23 C22 H22A 109.7 . . ? S2 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? S2 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C24 C23 C28 119.2(18) . . ? C24 C23 C22 120.1(17) . . ? C28 C23 C22 120.6(14) . . ? C25 C24 C23 119(2) . . ? C25 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C26 C25 C24 121.0(18) . . ? C26 C25 H25A 119.5 . . ? C24 C25 H25A 119.5 . . ? C27 C26 C25 120(2) . . ? C27 C26 H26A 120.2 . . ? C25 C26 H26A 120.2 . . ? C26 C27 C28 122.1(19) . . ? C26 C27 H27A 119.0 . . ? C28 C27 H27A 119.0 . . ? C27 C28 C23 118.6(15) . . ? C27 C28 Bi2 119.0(11) . . ? C23 C28 Bi2 122.1(12) . . ? C30 C29 C34 123.0(17) . . ? C30 C29 Bi3 115.8(13) . . ? C34 C29 Bi3 120.8(12) . . ? C29 C30 C31 116(2) . . ? C29 C30 H30A 121.8 . . ? C31 C30 H30A 121.8 . . ? C32 C31 C30 119(2) . . ? C32 C31 H31A 120.6 . . ? C30 C31 H31A 120.6 . . ? C33 C32 C31 122(2) . . ? C33 C32 H32A 119.0 . . ? C31 C32 H32A 119.0 . . ? C32 C33 C34 120(2) . . ? C32 C33 H33A 120.2 . . ? C34 C33 H33A 120.2 . . ? C33 C34 C29 119.9(19) . . ? C33 C34 C35 116.7(17) . . ? C29 C34 C35 123.4(16) . . ? C34 C35 S3 109.2(11) . . ? C34 C35 H35A 109.8 . . ? S3 C35 H35A 109.8 . . ? C34 C35 H35B 109.8 . . ? S3 C35 H35B 109.8 . . ? H35A C35 H35B 108.3 . . ? C37 C36 S3 112.8(11) . . ? C37 C36 H36A 109.0 . . ? S3 C36 H36A 109.0 . . ? C37 C36 H36B 109.0 . . ? S3 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C42 C37 C38 119.7(15) . . ? C42 C37 C36 123.8(13) . . ? C38 C37 C36 116.5(14) . . ? C37 C38 C39 119.6(16) . . ? C37 C38 H38A 120.2 . . ? C39 C38 H38A 120.2 . . ? C40 C39 C38 121.1(16) . . ? C40 C39 H39A 119.4 . . ? C38 C39 H39A 119.4 . . ? C39 C40 C41 120.6(16) . . ? C39 C40 H40A 119.7 . . ? C41 C40 H40A 119.7 . . ? C42 C41 C40 119.5(17) . . ? C42 C41 H41A 120.3 . . ? C40 C41 H41A 120.3 . . ? C37 C42 C41 119.1(15) . . ? C37 C42 Bi3 119.3(10) . . ? C41 C42 Bi3 120.9(11) . . ? C44 C43 C48 117.5(17) . . ? C44 C43 Bi4 119.5(13) . . ? C48 C43 Bi4 122.6(12) . . ? C45 C44 C43 119(2) . . ? C45 C44 H44A 120.3 . . ? C43 C44 H44A 120.3 . . ? C46 C45 C44 124(2) . . ? C46 C45 H45A 118.1 . . ? C44 C45 H45A 118.1 . . ? C45 C46 C47 117(2) . . ? C45 C46 H46A 121.4 . . ? C47 C46 H46A 121.4 . . ? C46 C47 C48 122(2) . . ? C46 C47 H47A 119.2 . . ? C48 C47 H47A 119.2 . . ? C47 C48 C43 120.1(18) . . ? C47 C48 C49 120.0(18) . . ? C43 C48 C49 119.7(16) . . ? C48 C49 S4 111.5(12) . . ? C48 C49 H49A 109.3 . . ? S4 C49 H49A 109.3 . . ? C48 C49 H49B 109.3 . . ? S4 C49 H49B 109.3 . . ? H49A C49 H49B 108.0 . . ? C51 C50 S4 113.6(11) . . ? C51 C50 H50A 108.9 . . ? S4 C50 H50A 108.9 . . ? C51 C50 H50B 108.9 . . ? S4 C50 H50B 108.9 . . ? H50A C50 H50B 107.7 . . ? C56 C51 C52 119.6(16) . . ? C56 C51 C50 122.9(14) . . ? C52 C51 C50 117.3(15) . . ? C53 C52 C51 120.8(17) . . ? C53 C52 H52A 119.6 . . ? C51 C52 H52A 119.6 . . ? C54 C53 C52 117.8(17) . . ? C54 C53 H53A 121.1 . . ? C52 C53 H53A 121.1 . . ? C53 C54 C55 124.9(17) . . ? C53 C54 H54A 117.5 . . ? C55 C54 H54A 117.5 . . ? C54 C55 C56 118.5(16) . . ? C54 C55 H55A 120.8 . . ? C56 C55 H55A 120.8 . . ? C51 C56 C55 118.2(14) . . ? C51 C56 Bi4 119.9(11) . . ? C55 C56 Bi4 121.9(11) . . ? C7 S1 C8 103.9(9) . . ? C7 S1 Bi1 92.5(6) . . ? C8 S1 Bi1 91.9(6) . . ? C22 S2 C21 101.2(9) . . ? C22 S2 Bi2 93.3(6) . . ? C21 S2 Bi2 90.2(6) . . ? C36 S3 C35 102.7(8) . . ? C36 S3 Bi3 91.3(6) . . ? C35 S3 Bi3 92.3(6) . . ? C49 S4 C50 102.4(8) . . ? C49 S4 Bi4 91.5(6) . . ? C50 S4 Bi4 89.3(6) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 2.829 _refine_diff_density_min -2.213 _refine_diff_density_rms 0.230 # Attachment 'WY1964WM cpd 5b.CIF' data_5b _database_code_depnum_ccdc_archive 'CCDC 724772' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H42 Bi Ge N O2' _chemical_formula_weight 862.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9433(4) _cell_length_b 19.9454(9) _cell_length_c 20.0095(9) _cell_angle_alpha 78.9480(10) _cell_angle_beta 88.4360(10) _cell_angle_gamma 88.3540(10) _cell_volume 3500.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 5.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5363 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17084 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11974 _reflns_number_gt 10717 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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^)+(0.0428P)^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_number_reflns 11974 _refine_ls_number_parameters 829 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _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 0.450387(14) 0.400997(6) 0.877842(6) 0.02268(5) Uani 1 1 d . . . Bi2 Bi 0.088965(13) 0.898385(6) 0.379635(6) 0.02161(5) Uani 1 1 d . . . C1 C 0.2117(4) 0.41244(17) 0.84693(16) 0.0229(7) Uani 1 1 d . . . C2 C 0.1593(4) 0.46801(18) 0.80039(18) 0.0299(8) Uani 1 1 d . . . H2A H 0.2272 0.5018 0.7792 0.036 Uiso 1 1 calc R . . C3 C 0.0088(4) 0.4752(2) 0.78406(19) 0.0338(9) Uani 1 1 d . . . H3A H -0.0259 0.5139 0.7523 0.041 Uiso 1 1 calc R . . C4 C -0.0896(4) 0.4259(2) 0.81427(19) 0.0346(9) Uani 1 1 d . . . H4A H -0.1924 0.4301 0.8030 0.042 Uiso 1 1 calc R . . C5 C -0.0382(4) 0.3703(2) 0.86112(18) 0.0305(8) Uani 1 1 d . . . H5A H -0.1065 0.3364 0.8817 0.037 Uiso 1 1 calc R . . C6 C 0.1121(4) 0.36311(17) 0.87850(17) 0.0230(7) Uani 1 1 d . . . C7 C 0.1646(4) 0.30085(18) 0.92819(18) 0.0284(8) Uani 1 1 d . . . H7A H 0.0859 0.2884 0.9638 0.034 Uiso 1 1 calc R . . H7B H 0.1784 0.2622 0.9039 0.034 Uiso 1 1 calc R . . C8 C 0.2875(4) 0.33036(18) 1.02951(17) 0.0290(8) Uani 1 1 d . . . H8A H 0.3901 0.3379 1.0449 0.035 Uiso 1 1 calc R . . C9 C 0.2001(5) 0.39780(19) 1.02546(19) 0.0346(9) Uani 1 1 d . . . H9A H 0.0962 0.3923 1.0119 0.042 Uiso 1 1 calc R . . H9B H 0.2469 0.4334 0.9904 0.042 Uiso 1 1 calc R . . C10 C 0.1985(6) 0.4202(2) 1.0944(2) 0.0514(12) Uani 1 1 d . . . H10A H 0.3018 0.4296 1.1058 0.062 Uiso 1 1 calc R . . H10B H 0.1380 0.4630 1.0915 0.062 Uiso 1 1 calc R . . C11 C 0.1337(6) 0.3657(3) 1.1506(2) 0.0554(13) Uani 1 1 d . . . H11A H 0.1395 0.3807 1.1948 0.066 Uiso 1 1 calc R . . H11B H 0.0269 0.3598 1.1418 0.066 Uiso 1 1 calc R . . C12 C 0.2179(6) 0.2980(3) 1.1543(2) 0.0513(12) Uani 1 1 d . . . H12A H 0.1702 0.2628 1.1893 0.062 Uiso 1 1 calc R . . H12B H 0.3223 0.3027 1.1677 0.062 Uiso 1 1 calc R . . C13 C 0.2178(5) 0.2757(2) 1.08470(18) 0.0374(9) Uani 1 1 d . . . H13A H 0.2752 0.2321 1.0875 0.045 Uiso 1 1 calc R . . H13B H 0.1138 0.2680 1.0727 0.045 Uiso 1 1 calc R . . C14 C 0.4049(4) 0.24870(17) 0.96522(18) 0.0284(8) Uani 1 1 d . . . H14A H 0.3480 0.2077 0.9856 0.034 Uiso 1 1 calc R . . H14B H 0.4902 0.2518 0.9949 0.034 Uiso 1 1 calc R . . C15 C 0.4634(4) 0.24169(19) 0.89510(19) 0.0294(8) Uani 1 1 d . . . C16 C 0.4860(5) 0.17791(19) 0.8783(2) 0.0370(9) Uani 1 1 d . . . H16A H 0.4560 0.1383 0.9097 0.044 Uiso 1 1 calc R . . C17 C 0.5521(5) 0.1709(2) 0.8161(2) 0.0428(10) Uani 1 1 d . . . H17A H 0.5669 0.1270 0.8051 0.051 Uiso 1 1 calc R . . C18 C 0.5959(5) 0.2283(2) 0.7708(2) 0.0439(10) Uani 1 1 d . . . H18A H 0.6435 0.2237 0.7289 0.053 Uiso 1 1 calc R . . C19 C 0.5711(4) 0.2928(2) 0.78596(19) 0.0355(9) Uani 1 1 d . . . H19A H 0.6005 0.3322 0.7542 0.043 Uiso 1 1 calc R . . C20 C 0.5030(4) 0.29976(17) 0.84765(18) 0.0270(8) Uani 1 1 d . . . C21 C 0.5400(4) 0.51005(18) 0.75787(17) 0.0255(7) Uani 1 1 d . . . C22 C 0.6180(4) 0.54036(17) 0.69019(18) 0.0265(8) Uani 1 1 d . . . H22A H 0.7233 0.5235 0.6914 0.032 Uiso 1 1 calc R . . H22B H 0.5690 0.5235 0.6530 0.032 Uiso 1 1 calc R . . C23 C 0.6161(4) 0.61852(17) 0.67356(18) 0.0255(7) Uani 1 1 d . . . H23A H 0.6557 0.6358 0.7126 0.031 Uiso 1 1 calc R . . H23B H 0.5114 0.6355 0.6672 0.031 Uiso 1 1 calc R . . C24 C 0.7662(4) 0.75202(17) 0.58763(18) 0.0264(8) Uani 1 1 d . . . C25 C 0.7554(4) 0.80012(18) 0.52815(19) 0.0291(8) Uani 1 1 d . . . H25A H 0.7307 0.7859 0.4872 0.035 Uiso 1 1 calc R . . C26 C 0.7799(4) 0.86906(19) 0.5269(2) 0.0362(9) Uani 1 1 d . . . H26A H 0.7691 0.9016 0.4859 0.043 Uiso 1 1 calc R . . C27 C 0.8197(5) 0.8894(2) 0.5854(2) 0.0446(11) Uani 1 1 d . . . H27A H 0.8380 0.9362 0.5847 0.054 Uiso 1 1 calc R . . C28 C 0.8335(5) 0.8423(2) 0.6451(2) 0.0468(11) Uani 1 1 d . . . H28A H 0.8631 0.8565 0.6854 0.056 Uiso 1 1 calc R . . C29 C 0.8042(5) 0.77408(19) 0.6465(2) 0.0365(9) Uani 1 1 d . . . H29A H 0.8101 0.7421 0.6883 0.044 Uiso 1 1 calc R . . C30 C 0.6368(4) 0.63877(17) 0.51017(17) 0.0248(7) Uani 1 1 d . . . C31 C 0.5007(4) 0.60625(18) 0.5162(2) 0.0322(8) Uani 1 1 d . . . H31A H 0.4549 0.5931 0.5600 0.039 Uiso 1 1 calc R . . C32 C 0.4301(5) 0.5925(2) 0.4594(2) 0.0405(10) Uani 1 1 d . . . H32A H 0.3375 0.5697 0.4646 0.049 Uiso 1 1 calc R . . C33 C 0.4943(5) 0.6119(2) 0.3960(2) 0.0407(10) Uani 1 1 d . . . H33A H 0.4463 0.6024 0.3572 0.049 Uiso 1 1 calc R . . C34 C 0.6279(5) 0.6449(2) 0.3883(2) 0.0396(10) Uani 1 1 d . . . H34A H 0.6712 0.6590 0.3441 0.047 Uiso 1 1 calc R . . C35 C 0.7001(4) 0.65783(19) 0.44514(18) 0.0315(8) Uani 1 1 d . . . H35A H 0.7935 0.6799 0.4395 0.038 Uiso 1 1 calc R . . C36 C 0.9287(4) 0.60658(17) 0.60008(17) 0.0246(7) Uani 1 1 d . . . C37 C 1.0445(4) 0.62896(18) 0.63556(19) 0.0299(8) Uani 1 1 d . . . H37A H 1.0328 0.6709 0.6512 0.036 Uiso 1 1 calc R . . C38 C 1.1759(4) 0.5905(2) 0.6480(2) 0.0380(9) Uani 1 1 d . . . H38A H 1.2530 0.6058 0.6728 0.046 Uiso 1 1 calc R . . C39 C 1.1951(4) 0.5296(2) 0.6243(2) 0.0376(9) Uani 1 1 d . . . H39A H 1.2855 0.5034 0.6327 0.045 Uiso 1 1 calc R . . C40 C 1.0844(5) 0.5074(2) 0.5891(2) 0.0381(9) Uani 1 1 d . . . H40A H 1.0983 0.4662 0.5724 0.046 Uiso 1 1 calc R . . C41 C 0.9511(4) 0.54510(19) 0.57745(19) 0.0323(8) Uani 1 1 d . . . H41A H 0.8740 0.5286 0.5536 0.039 Uiso 1 1 calc R . . C42 C 0.3300(4) 0.90777(17) 0.34705(17) 0.0237(7) Uani 1 1 d . . . C43 C 0.3815(4) 0.96382(18) 0.29965(19) 0.0297(8) Uani 1 1 d . . . H43A H 0.3130 0.9990 0.2801 0.036 Uiso 1 1 calc R . . C44 C 0.5308(4) 0.9682(2) 0.28119(19) 0.0339(9) Uani 1 1 d . . . H44A H 0.5650 1.0064 0.2490 0.041 Uiso 1 1 calc R . . C45 C 0.6309(4) 0.9174(2) 0.30918(19) 0.0337(9) Uani 1 1 d . . . H45A H 0.7336 0.9202 0.2957 0.040 Uiso 1 1 calc R . . C46 C 0.5818(4) 0.86205(19) 0.35714(18) 0.0305(8) Uani 1 1 d . . . H46A H 0.6511 0.8269 0.3760 0.037 Uiso 1 1 calc R . . C47 C 0.4311(4) 0.85762(18) 0.37796(17) 0.0245(7) Uani 1 1 d . . . C48 C 0.3812(4) 0.79700(17) 0.42907(18) 0.0264(8) Uani 1 1 d . . . H48A H 0.3733 0.7576 0.4060 0.032 Uiso 1 1 calc R . . H48B H 0.4584 0.7851 0.4642 0.032 Uiso 1 1 calc R . . C49 C 0.2464(4) 0.82965(19) 0.53096(17) 0.0297(8) Uani 1 1 d . . . H49A H 0.1418 0.8372 0.5473 0.036 Uiso 1 1 calc R . . C50 C 0.3253(5) 0.89747(19) 0.52488(19) 0.0349(9) Uani 1 1 d . . . H50A H 0.2756 0.9326 0.4903 0.042 Uiso 1 1 calc R . . H50B H 0.4306 0.8921 0.5098 0.042 Uiso 1 1 calc R . . C51 C 0.3206(6) 0.9208(2) 0.5938(2) 0.0547(12) Uani 1 1 d . . . H51A H 0.3770 0.9635 0.5896 0.066 Uiso 1 1 calc R . . H51B H 0.2156 0.9308 0.6062 0.066 Uiso 1 1 calc R . . C52 C 0.3868(6) 0.8673(3) 0.6495(2) 0.0565(13) Uani 1 1 d . . . H52A H 0.3740 0.8825 0.6936 0.068 Uiso 1 1 calc R . . H52B H 0.4954 0.8618 0.6404 0.068 Uiso 1 1 calc R . . C53 C 0.3126(6) 0.7991(3) 0.6542(2) 0.0534(12) Uani 1 1 d . . . H53A H 0.2068 0.8031 0.6690 0.064 Uiso 1 1 calc R . . H53B H 0.3633 0.7643 0.6887 0.064 Uiso 1 1 calc R . . C54 C 0.3195(5) 0.7759(2) 0.58597(19) 0.0378(9) Uani 1 1 d . . . H54A H 0.2673 0.7322 0.5901 0.045 Uiso 1 1 calc R . . H54B H 0.4252 0.7682 0.5728 0.045 Uiso 1 1 calc R . . C55 C 0.1437(4) 0.74657(18) 0.46888(18) 0.0283(8) Uani 1 1 d . . . H55A H 0.0567 0.7499 0.4998 0.034 Uiso 1 1 calc R . . H55B H 0.2044 0.7056 0.4886 0.034 Uiso 1 1 calc R . . C56 C 0.0897(4) 0.73933(18) 0.39966(19) 0.0277(8) Uani 1 1 d . . . C57 C 0.0754(4) 0.67441(19) 0.3845(2) 0.0365(9) Uani 1 1 d . . . H57A H 0.1038 0.6351 0.4169 0.044 Uiso 1 1 calc R . . C58 C 0.0202(5) 0.6670(2) 0.3227(2) 0.0450(11) Uani 1 1 d . . . H58A H 0.0123 0.6227 0.3124 0.054 Uiso 1 1 calc R . . C59 C -0.0236(5) 0.7238(2) 0.2759(2) 0.0443(10) Uani 1 1 d . . . H59A H -0.0656 0.7187 0.2341 0.053 Uiso 1 1 calc R . . C60 C -0.0060(4) 0.7884(2) 0.28997(19) 0.0336(9) Uani 1 1 d . . . H60A H -0.0342 0.8276 0.2573 0.040 Uiso 1 1 calc R . . C61 C 0.0524(4) 0.79625(17) 0.35142(18) 0.0258(8) Uani 1 1 d . . . C62 C -0.0036(4) 1.00662(17) 0.25948(17) 0.0239(7) Uani 1 1 d . . . C63 C -0.0767(4) 1.03826(17) 0.19286(17) 0.0257(8) Uani 1 1 d . . . H63A H -0.1792 1.0207 0.1934 0.031 Uiso 1 1 calc R . . H63B H -0.0198 1.0230 0.1551 0.031 Uiso 1 1 calc R . . C64 C -0.0859(4) 1.11646(17) 0.17819(17) 0.0262(8) Uani 1 1 d . . . H64A H 0.0169 1.1343 0.1729 0.031 Uiso 1 1 calc R . . H64B H -0.1343 1.1321 0.2177 0.031 Uiso 1 1 calc R . . C65 C -0.0901(4) 1.13742(17) 0.01515(18) 0.0274(8) Uani 1 1 d . . . C66 C 0.0566(4) 1.11271(18) 0.0194(2) 0.0331(9) Uani 1 1 d . . . H66A H 0.1045 1.1048 0.0621 0.040 Uiso 1 1 calc R . . C67 C 0.1346(5) 1.09936(19) -0.0381(2) 0.0387(10) Uani 1 1 d . . . H67A H 0.2349 1.0823 -0.0344 0.046 Uiso 1 1 calc R . . C68 C 0.0665(5) 1.1110(2) -0.1004(2) 0.0439(11) Uani 1 1 d . . . H68A H 0.1197 1.1021 -0.1396 0.053 Uiso 1 1 calc R . . C69 C -0.0792(5) 1.1355(2) -0.1055(2) 0.0485(11) Uani 1 1 d . . . H69A H -0.1268 1.1432 -0.1482 0.058 Uiso 1 1 calc R . . C70 C -0.1569(5) 1.1491(2) -0.0479(2) 0.0411(10) Uani 1 1 d . . . H70A H -0.2569 1.1665 -0.0519 0.049 Uiso 1 1 calc R . . C71 C -0.3893(4) 1.10951(17) 0.10472(18) 0.0276(8) Uani 1 1 d . . . C72 C -0.4105(5) 1.0521(2) 0.0764(2) 0.0363(9) Uani 1 1 d . . . H72A H -0.3330 1.0371 0.0489 0.044 Uiso 1 1 calc R . . C73 C -0.5413(5) 1.0165(2) 0.0873(2) 0.0422(10) Uani 1 1 d . . . H73A H -0.5539 0.9779 0.0668 0.051 Uiso 1 1 calc R . . C74 C -0.6540(5) 1.0368(2) 0.1280(2) 0.0469(11) Uani 1 1 d . . . H74A H -0.7432 1.0116 0.1366 0.056 Uiso 1 1 calc R . . C75 C -0.6365(5) 1.0942(2) 0.1562(2) 0.0423(10) Uani 1 1 d . . . H75A H -0.7147 1.1087 0.1836 0.051 Uiso 1 1 calc R . . C76 C -0.5053(4) 1.1305(2) 0.1448(2) 0.0354(9) Uani 1 1 d . . . H76A H -0.4944 1.1699 0.1643 0.042 Uiso 1 1 calc R . . C77 C -0.2320(4) 1.25252(17) 0.09201(18) 0.0287(8) Uani 1 1 d . . . C78 C -0.2235(4) 1.29919(18) 0.0313(2) 0.0314(8) Uani 1 1 d . . . H78A H -0.1968 1.2838 -0.0096 0.038 Uiso 1 1 calc R . . C79 C -0.2534(5) 1.36835(19) 0.0293(2) 0.0398(10) Uani 1 1 d . . . H79A H -0.2445 1.4001 -0.0125 0.048 Uiso 1 1 calc R . . C80 C -0.2960(5) 1.3907(2) 0.0881(3) 0.0508(12) Uani 1 1 d . . . H80A H -0.3176 1.4378 0.0868 0.061 Uiso 1 1 calc R . . C81 C -0.3073(6) 1.3450(2) 0.1484(3) 0.0537(13) Uani 1 1 d . . . H81A H -0.3381 1.3605 0.1888 0.064 Uiso 1 1 calc R . . C82 C -0.2742(5) 1.2766(2) 0.1510(2) 0.0420(10) Uani 1 1 d . . . H82A H -0.2802 1.2456 0.1933 0.050 Uiso 1 1 calc R . . Ge1 Ge 0.73498(4) 0.654906(17) 0.591321(18) 0.02231(8) Uani 1 1 d . . . Ge2 Ge -0.19698(4) 1.154673(18) 0.096692(18) 0.02428(9) Uani 1 1 d . . . N1 N 0.3065(3) 0.31049(14) 0.96145(14) 0.0238(6) Uani 1 1 d . . . N2 N 0.2348(3) 0.80822(14) 0.46314(14) 0.0244(6) Uani 1 1 d . . . O1 O 0.5276(3) 0.44494(12) 0.76811(12) 0.0299(6) Uani 1 1 d . . . O2 O 0.4971(4) 0.54597(13) 0.79758(14) 0.0443(7) Uani 1 1 d . . . O3 O 0.0163(3) 0.94122(12) 0.26975(12) 0.0277(5) Uani 1 1 d . . . O4 O 0.0319(4) 1.04131(14) 0.30050(15) 0.0517(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02425(8) 0.02139(8) 0.02131(8) -0.00105(5) -0.00040(5) -0.00279(5) Bi2 0.02254(8) 0.01997(8) 0.02118(8) -0.00098(5) 0.00073(5) -0.00227(5) C1 0.0258(18) 0.0236(17) 0.0194(17) -0.0045(14) 0.0004(14) 0.0005(14) C2 0.032(2) 0.0251(19) 0.031(2) -0.0016(16) 0.0007(16) -0.0001(15) C3 0.034(2) 0.033(2) 0.030(2) 0.0040(17) -0.0034(16) 0.0058(17) C4 0.027(2) 0.045(2) 0.030(2) -0.0034(18) -0.0019(16) 0.0038(17) C5 0.030(2) 0.037(2) 0.0236(19) -0.0030(16) 0.0020(15) -0.0049(16) C6 0.0240(18) 0.0267(18) 0.0187(17) -0.0055(14) 0.0014(13) -0.0022(14) C7 0.030(2) 0.0273(19) 0.0272(19) -0.0023(15) -0.0005(15) -0.0048(15) C8 0.031(2) 0.033(2) 0.0218(18) -0.0009(15) -0.0003(15) -0.0010(16) C9 0.045(2) 0.033(2) 0.026(2) -0.0054(16) 0.0023(17) 0.0004(17) C10 0.068(3) 0.052(3) 0.037(2) -0.018(2) 0.002(2) 0.004(2) C11 0.068(3) 0.071(3) 0.028(2) -0.014(2) 0.008(2) 0.010(3) C12 0.059(3) 0.069(3) 0.022(2) -0.001(2) 0.0052(19) 0.006(2) C13 0.046(2) 0.038(2) 0.024(2) 0.0033(17) 0.0046(17) 0.0011(18) C14 0.029(2) 0.0216(18) 0.031(2) 0.0037(15) 0.0007(16) -0.0012(15) C15 0.0282(19) 0.0284(19) 0.031(2) -0.0045(16) -0.0010(15) 0.0006(15) C16 0.040(2) 0.0245(19) 0.045(2) -0.0033(18) -0.0005(19) -0.0002(17) C17 0.047(3) 0.033(2) 0.051(3) -0.018(2) 0.000(2) 0.0027(19) C18 0.051(3) 0.047(3) 0.036(2) -0.016(2) 0.001(2) 0.007(2) C19 0.040(2) 0.035(2) 0.029(2) -0.0015(17) -0.0003(17) 0.0017(17) C20 0.032(2) 0.0239(18) 0.0248(18) -0.0049(15) -0.0012(15) 0.0044(15) C21 0.0214(18) 0.0284(19) 0.0241(18) 0.0016(15) -0.0012(14) -0.0010(14) C22 0.0292(19) 0.0232(18) 0.0257(18) -0.0012(15) 0.0038(15) -0.0029(15) C23 0.0244(18) 0.0212(17) 0.0306(19) -0.0031(15) -0.0004(15) -0.0060(14) C24 0.0248(18) 0.0224(18) 0.0311(19) -0.0024(15) -0.0034(15) -0.0040(14) C25 0.0283(19) 0.0262(19) 0.031(2) -0.0001(16) -0.0042(15) -0.0035(15) C26 0.035(2) 0.0248(19) 0.045(2) 0.0032(17) 0.0017(18) -0.0011(16) C27 0.051(3) 0.022(2) 0.061(3) -0.009(2) 0.003(2) -0.0104(18) C28 0.066(3) 0.033(2) 0.046(3) -0.014(2) -0.008(2) -0.013(2) C29 0.054(3) 0.028(2) 0.026(2) -0.0025(16) -0.0013(18) -0.0083(18) C30 0.0278(19) 0.0221(17) 0.0244(18) -0.0034(14) -0.0056(14) -0.0007(14) C31 0.035(2) 0.028(2) 0.031(2) 0.0030(16) -0.0075(16) -0.0101(16) C32 0.043(2) 0.030(2) 0.048(3) -0.0026(19) -0.018(2) -0.0083(18) C33 0.058(3) 0.029(2) 0.037(2) -0.0081(18) -0.018(2) 0.0029(19) C34 0.051(3) 0.039(2) 0.029(2) -0.0092(18) -0.0030(18) 0.006(2) C35 0.030(2) 0.033(2) 0.031(2) -0.0073(17) 0.0003(16) 0.0015(16) C36 0.0280(19) 0.0227(18) 0.0211(17) 0.0011(14) 0.0015(14) -0.0039(14) C37 0.028(2) 0.0226(18) 0.036(2) 0.0014(16) 0.0018(16) -0.0089(15) C38 0.025(2) 0.039(2) 0.046(2) 0.0036(19) -0.0055(18) -0.0106(17) C39 0.027(2) 0.032(2) 0.046(2) 0.0108(18) 0.0049(18) 0.0020(16) C40 0.042(2) 0.033(2) 0.037(2) -0.0012(18) 0.0080(18) 0.0024(18) C41 0.036(2) 0.030(2) 0.030(2) -0.0021(16) -0.0035(16) -0.0019(16) C42 0.0234(18) 0.0240(18) 0.0241(18) -0.0051(15) 0.0034(14) -0.0083(14) C43 0.029(2) 0.0247(19) 0.032(2) 0.0046(16) -0.0007(16) -0.0042(15) C44 0.031(2) 0.034(2) 0.032(2) 0.0068(17) -0.0003(16) -0.0120(17) C45 0.0242(19) 0.043(2) 0.031(2) 0.0021(17) 0.0010(16) -0.0110(17) C46 0.0265(19) 0.035(2) 0.0271(19) 0.0032(16) -0.0036(15) -0.0018(16) C47 0.0250(18) 0.0270(18) 0.0215(17) -0.0047(14) -0.0002(14) -0.0021(14) C48 0.0238(18) 0.0269(19) 0.0259(19) 0.0007(15) 0.0045(14) -0.0009(15) C49 0.0277(19) 0.038(2) 0.0226(18) -0.0039(16) 0.0012(15) -0.0005(16) C50 0.044(2) 0.032(2) 0.028(2) -0.0048(16) -0.0081(17) 0.0010(17) C51 0.071(3) 0.056(3) 0.044(3) -0.023(2) -0.005(2) -0.003(2) C52 0.059(3) 0.081(4) 0.033(2) -0.019(2) -0.009(2) -0.001(3) C53 0.060(3) 0.074(3) 0.023(2) 0.000(2) -0.003(2) -0.002(3) C54 0.040(2) 0.043(2) 0.026(2) 0.0034(17) -0.0012(17) -0.0037(18) C55 0.0266(19) 0.0252(18) 0.031(2) 0.0005(15) 0.0042(15) -0.0044(15) C56 0.0255(19) 0.0250(18) 0.031(2) -0.0011(16) 0.0040(15) -0.0051(15) C57 0.037(2) 0.0241(19) 0.046(2) -0.0018(18) 0.0076(18) -0.0094(16) C58 0.057(3) 0.032(2) 0.050(3) -0.017(2) 0.011(2) -0.014(2) C59 0.063(3) 0.039(2) 0.034(2) -0.0138(19) 0.000(2) -0.013(2) C60 0.039(2) 0.033(2) 0.029(2) -0.0047(17) 0.0005(17) -0.0074(17) C61 0.0226(18) 0.0246(18) 0.0305(19) -0.0063(15) 0.0063(15) -0.0061(14) C62 0.0195(17) 0.0249(18) 0.0260(18) -0.0007(15) 0.0000(14) -0.0056(14) C63 0.0262(19) 0.0229(18) 0.0272(19) -0.0026(15) -0.0015(15) -0.0045(14) C64 0.031(2) 0.0202(17) 0.0255(18) 0.0000(15) -0.0014(15) -0.0014(14) C65 0.033(2) 0.0213(18) 0.0268(19) -0.0022(15) 0.0055(15) -0.0025(15) C66 0.039(2) 0.0263(19) 0.032(2) -0.0022(16) 0.0039(17) 0.0031(16) C67 0.040(2) 0.029(2) 0.045(2) -0.0037(18) 0.0133(19) 0.0022(17) C68 0.058(3) 0.040(2) 0.036(2) -0.014(2) 0.015(2) -0.006(2) C69 0.057(3) 0.065(3) 0.025(2) -0.011(2) -0.0002(19) -0.008(2) C70 0.035(2) 0.056(3) 0.032(2) -0.007(2) -0.0004(17) 0.0027(19) C71 0.029(2) 0.0221(18) 0.0271(19) 0.0055(15) 0.0009(15) -0.0023(15) C72 0.037(2) 0.032(2) 0.039(2) -0.0038(18) -0.0032(18) 0.0002(17) C73 0.044(3) 0.033(2) 0.046(3) 0.0018(19) -0.009(2) -0.0075(19) C74 0.034(2) 0.048(3) 0.048(3) 0.019(2) -0.010(2) -0.007(2) C75 0.030(2) 0.044(2) 0.044(2) 0.011(2) 0.0044(18) 0.0084(18) C76 0.032(2) 0.034(2) 0.037(2) 0.0002(18) 0.0008(17) 0.0048(17) C77 0.029(2) 0.0241(18) 0.0306(19) -0.0014(15) 0.0036(15) 0.0013(15) C78 0.030(2) 0.0277(19) 0.035(2) -0.0009(16) 0.0002(16) -0.0022(15) C79 0.039(2) 0.025(2) 0.049(3) 0.0096(18) -0.0046(19) -0.0034(17) C80 0.062(3) 0.024(2) 0.065(3) -0.007(2) -0.001(2) 0.008(2) C81 0.073(3) 0.039(3) 0.052(3) -0.018(2) 0.011(2) 0.008(2) C82 0.062(3) 0.031(2) 0.031(2) -0.0016(17) 0.0063(19) 0.0037(19) Ge1 0.02399(19) 0.01950(18) 0.02252(18) -0.00080(14) -0.00243(14) -0.00484(14) Ge2 0.0280(2) 0.02063(18) 0.02227(19) 0.00019(15) 0.00188(15) 0.00039(15) N1 0.0272(16) 0.0218(15) 0.0200(14) 0.0015(12) 0.0002(12) -0.0013(12) N2 0.0248(15) 0.0231(15) 0.0225(15) 0.0025(12) 0.0028(12) -0.0051(12) O1 0.0363(15) 0.0252(13) 0.0258(13) 0.0010(10) 0.0037(11) -0.0063(11) O2 0.065(2) 0.0323(15) 0.0347(16) -0.0067(13) 0.0199(14) -0.0049(14) O3 0.0338(14) 0.0230(13) 0.0249(13) -0.0005(10) -0.0054(11) -0.0018(10) O4 0.089(2) 0.0265(15) 0.0415(17) -0.0057(13) -0.0324(17) -0.0005(15) _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 2.232(3) . ? Bi1 C20 2.250(3) . ? Bi1 O1 2.298(2) . ? Bi1 N1 2.563(3) . ? Bi2 C42 2.238(3) . ? Bi2 C61 2.250(3) . ? Bi2 O3 2.305(2) . ? Bi2 N2 2.561(3) . ? C1 C2 1.383(5) . ? C1 C6 1.393(5) . ? C2 C3 1.390(5) . ? C2 H2A 0.9500 . ? C3 C4 1.378(6) . ? C3 H3A 0.9500 . ? C4 C5 1.385(5) . ? C4 H4A 0.9500 . ? C5 C6 1.394(5) . ? C5 H5A 0.9500 . ? C6 C7 1.507(5) . ? C7 N1 1.483(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N1 1.494(4) . ? C8 C9 1.526(5) . ? C8 C13 1.529(5) . ? C8 H8A 1.0000 . ? C9 C10 1.530(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.520(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.541(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N1 1.485(4) . ? C14 C15 1.514(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.385(5) . ? C15 C20 1.397(5) . ? C16 C17 1.392(6) . ? C16 H16A 0.9500 . ? C17 C18 1.376(6) . ? C17 H17A 0.9500 . ? C18 C19 1.387(5) . ? C18 H18A 0.9500 . ? C19 C20 1.390(5) . ? C19 H19A 0.9500 . ? C21 O2 1.215(4) . ? C21 O1 1.283(4) . ? C21 C22 1.532(5) . ? C22 C23 1.530(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 Ge1 1.964(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.382(5) . ? C24 C29 1.388(5) . ? C24 Ge1 1.952(3) . ? C25 C26 1.394(5) . ? C25 H25A 0.9500 . ? C26 C27 1.367(6) . ? C26 H26A 0.9500 . ? C27 C28 1.378(6) . ? C27 H27A 0.9500 . ? C28 C29 1.387(5) . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? C30 C31 1.387(5) . ? C30 C35 1.393(5) . ? C30 Ge1 1.951(3) . ? C31 C32 1.391(5) . ? C31 H31A 0.9500 . ? C32 C33 1.369(6) . ? C32 H32A 0.9500 . ? C33 C34 1.371(6) . ? C33 H33A 0.9500 . ? C34 C35 1.392(5) . ? C34 H34A 0.9500 . ? C35 H35A 0.9500 . ? C36 C41 1.394(5) . ? C36 C37 1.401(5) . ? C36 Ge1 1.954(3) . ? C37 C38 1.387(5) . ? C37 H37A 0.9500 . ? C38 C39 1.391(5) . ? C38 H38A 0.9500 . ? C39 C40 1.361(6) . ? C39 H39A 0.9500 . ? C40 C41 1.392(5) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? C42 C47 1.394(5) . ? C42 C43 1.400(5) . ? C43 C44 1.376(5) . ? C43 H43A 0.9500 . ? C44 C45 1.379(5) . ? C44 H44A 0.9500 . ? C45 C46 1.389(5) . ? C45 H45A 0.9500 . ? C46 C47 1.400(5) . ? C46 H46A 0.9500 . ? C47 C48 1.496(5) . ? C48 N2 1.491(4) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 N2 1.506(4) . ? C49 C50 1.526(5) . ? C49 C54 1.528(5) . ? C49 H49A 1.0000 . ? C50 C51 1.537(5) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.509(7) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.516(7) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.521(6) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 N2 1.479(4) . ? C55 C56 1.513(5) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 C61 1.381(5) . ? C56 C57 1.396(5) . ? C57 C58 1.379(6) . ? C57 H57A 0.9500 . ? C58 C59 1.379(6) . ? C58 H58A 0.9500 . ? C59 C60 1.384(5) . ? C59 H59A 0.9500 . ? C60 C61 1.387(5) . ? C60 H60A 0.9500 . ? C62 O4 1.224(4) . ? C62 O3 1.289(4) . ? C62 C63 1.518(5) . ? C63 C64 1.531(4) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 Ge2 1.948(3) . ? C64 H64A 0.9900 . ? C64 H64B 0.9900 . ? C65 C70 1.386(5) . ? C65 C66 1.387(5) . ? C65 Ge2 1.951(3) . ? C66 C67 1.395(5) . ? C66 H66A 0.9500 . ? C67 C68 1.379(6) . ? C67 H67A 0.9500 . ? C68 C69 1.378(6) . ? C68 H68A 0.9500 . ? C69 C70 1.396(5) . ? C69 H69A 0.9500 . ? C70 H70A 0.9500 . ? C71 C72 1.391(5) . ? C71 C76 1.398(5) . ? C71 Ge2 1.953(4) . ? C72 C73 1.376(6) . ? C72 H72A 0.9500 . ? C73 C74 1.379(6) . ? C73 H73A 0.9500 . ? C74 C75 1.384(6) . ? C74 H74A 0.9500 . ? C75 C76 1.387(6) . ? C75 H75A 0.9500 . ? C76 H76A 0.9500 . ? C77 C78 1.383(5) . ? C77 C82 1.395(5) . ? C77 Ge2 1.952(3) . ? C78 C79 1.391(5) . ? C78 H78A 0.9500 . ? C79 C80 1.377(6) . ? C79 H79A 0.9500 . ? C80 C81 1.369(6) . ? C80 H80A 0.9500 . ? C81 C82 1.379(6) . ? C81 H81A 0.9500 . ? C82 H82A 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 C20 98.30(12) . . ? C1 Bi1 O1 90.55(11) . . ? C20 Bi1 O1 83.75(11) . . ? C1 Bi1 N1 73.62(11) . . ? C20 Bi1 N1 73.03(11) . . ? O1 Bi1 N1 149.26(9) . . ? C42 Bi2 C61 97.28(12) . . ? C42 Bi2 O3 90.69(11) . . ? C61 Bi2 O3 84.04(11) . . ? C42 Bi2 N2 73.36(11) . . ? C61 Bi2 N2 72.41(11) . . ? O3 Bi2 N2 149.17(8) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 Bi1 122.3(3) . . ? C6 C1 Bi1 118.1(2) . . ? C1 C2 C3 121.1(4) . . ? C1 C2 H2A 119.4 . . ? C3 C2 H2A 119.4 . . ? C4 C3 C2 119.5(4) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 C7 121.5(3) . . ? C5 C6 C7 119.5(3) . . ? N1 C7 C6 113.7(3) . . ? N1 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N1 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N1 C8 C9 112.1(3) . . ? N1 C8 C13 114.5(3) . . ? C9 C8 C13 109.8(3) . . ? N1 C8 H8A 106.7 . . ? C9 C8 H8A 106.7 . . ? C13 C8 H8A 106.7 . . ? C8 C9 C10 110.3(3) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 111.5(4) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 111.1(4) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 110.4(4) . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C8 C13 C12 110.4(3) . . ? C8 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C8 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? N1 C14 C15 110.9(3) . . ? N1 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C20 119.1(3) . . ? C16 C15 C14 120.8(3) . . ? C20 C15 C14 120.0(3) . . ? C15 C16 C17 121.0(4) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17A 120.3 . . ? C16 C17 H17A 120.3 . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C18 C19 C20 120.0(4) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C19 C20 C15 119.9(3) . . ? C19 C20 Bi1 123.9(3) . . ? C15 C20 Bi1 116.2(2) . . ? O2 C21 O1 124.7(3) . . ? O2 C21 C22 121.3(3) . . ? O1 C21 C22 114.0(3) . . ? C23 C22 C21 114.3(3) . . ? C23 C22 H22A 108.7 . . ? C21 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C21 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C22 C23 Ge1 112.7(2) . . ? C22 C23 H23A 109.0 . . ? Ge1 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? Ge1 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C25 C24 C29 118.1(3) . . ? C25 C24 Ge1 122.7(3) . . ? C29 C24 Ge1 119.2(3) . . ? C24 C25 C26 121.4(4) . . ? C24 C25 H25A 119.3 . . ? C26 C25 H25A 119.3 . . ? C27 C26 C25 119.4(4) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C26 C27 C28 120.3(4) . . ? C26 C27 H27A 119.8 . . ? C28 C27 H27A 119.8 . . ? C27 C28 C29 120.0(4) . . ? C27 C28 H28A 120.0 . . ? C29 C28 H28A 120.0 . . ? C28 C29 C24 120.7(4) . . ? C28 C29 H29A 119.6 . . ? C24 C29 H29A 119.6 . . ? C31 C30 C35 117.8(3) . . ? C31 C30 Ge1 120.0(3) . . ? C35 C30 Ge1 122.2(3) . . ? C30 C31 C32 121.2(4) . . ? C30 C31 H31A 119.4 . . ? C32 C31 H31A 119.4 . . ? C33 C32 C31 119.9(4) . . ? C33 C32 H32A 120.1 . . ? C31 C32 H32A 120.1 . . ? C32 C33 C34 120.2(4) . . ? C32 C33 H33A 119.9 . . ? C34 C33 H33A 119.9 . . ? C33 C34 C35 120.1(4) . . ? C33 C34 H34A 119.9 . . ? C35 C34 H34A 119.9 . . ? C34 C35 C30 120.8(4) . . ? C34 C35 H35A 119.6 . . ? C30 C35 H35A 119.6 . . ? C41 C36 C37 117.8(3) . . ? C41 C36 Ge1 121.1(3) . . ? C37 C36 Ge1 120.8(3) . . ? C38 C37 C36 120.6(3) . . ? C38 C37 H37A 119.7 . . ? C36 C37 H37A 119.7 . . ? C37 C38 C39 120.2(4) . . ? C37 C38 H38A 119.9 . . ? C39 C38 H38A 119.9 . . ? C40 C39 C38 120.0(4) . . ? C40 C39 H39A 120.0 . . ? C38 C39 H39A 120.0 . . ? C39 C40 C41 120.3(4) . . ? C39 C40 H40A 119.9 . . ? C41 C40 H40A 119.9 . . ? C40 C41 C36 121.2(4) . . ? C40 C41 H41A 119.4 . . ? C36 C41 H41A 119.4 . . ? C47 C42 C43 119.9(3) . . ? C47 C42 Bi2 118.1(2) . . ? C43 C42 Bi2 121.9(3) . . ? C44 C43 C42 120.3(3) . . ? C44 C43 H43A 119.8 . . ? C42 C43 H43A 119.8 . . ? C43 C44 C45 120.3(4) . . ? C43 C44 H44A 119.9 . . ? C45 C44 H44A 119.9 . . ? C44 C45 C46 120.0(4) . . ? C44 C45 H45A 120.0 . . ? C46 C45 H45A 120.0 . . ? C45 C46 C47 120.5(3) . . ? C45 C46 H46A 119.7 . . ? C47 C46 H46A 119.7 . . ? C42 C47 C46 118.8(3) . . ? C42 C47 C48 121.8(3) . . ? C46 C47 C48 119.3(3) . . ? N2 C48 C47 113.6(3) . . ? N2 C48 H48A 108.8 . . ? C47 C48 H48A 108.8 . . ? N2 C48 H48B 108.8 . . ? C47 C48 H48B 108.8 . . ? H48A C48 H48B 107.7 . . ? N2 C49 C50 112.2(3) . . ? N2 C49 C54 114.3(3) . . ? C50 C49 C54 109.8(3) . . ? N2 C49 H49A 106.7 . . ? C50 C49 H49A 106.7 . . ? C54 C49 H49A 106.7 . . ? C49 C50 C51 110.3(3) . . ? C49 C50 H50A 109.6 . . ? C51 C50 H50A 109.6 . . ? C49 C50 H50B 109.6 . . ? C51 C50 H50B 109.6 . . ? H50A C50 H50B 108.1 . . ? C52 C51 C50 111.9(4) . . ? C52 C51 H51A 109.2 . . ? C50 C51 H51A 109.2 . . ? C52 C51 H51B 109.2 . . ? C50 C51 H51B 109.2 . . ? H51A C51 H51B 107.9 . . ? C51 C52 C53 111.3(4) . . ? C51 C52 H52A 109.4 . . ? C53 C52 H52A 109.4 . . ? C51 C52 H52B 109.4 . . ? C53 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? C52 C53 C54 111.3(4) . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53B 109.4 . . ? C54 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C53 C54 C49 110.6(3) . . ? C53 C54 H54A 109.5 . . ? C49 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? C49 C54 H54B 109.5 . . ? H54A C54 H54B 108.1 . . ? N2 C55 C56 110.5(3) . . ? N2 C55 H55A 109.5 . . ? C56 C55 H55A 109.5 . . ? N2 C55 H55B 109.5 . . ? C56 C55 H55B 109.5 . . ? H55A C55 H55B 108.1 . . ? C61 C56 C57 119.4(3) . . ? C61 C56 C55 120.8(3) . . ? C57 C56 C55 119.8(3) . . ? C58 C57 C56 120.4(4) . . ? C58 C57 H57A 119.8 . . ? C56 C57 H57A 119.8 . . ? C57 C58 C59 120.1(4) . . ? C57 C58 H58A 119.9 . . ? C59 C58 H58A 119.9 . . ? C58 C59 C60 119.7(4) . . ? C58 C59 H59A 120.1 . . ? C60 C59 H59A 120.1 . . ? C59 C60 C61 120.5(4) . . ? C59 C60 H60A 119.8 . . ? C61 C60 H60A 119.8 . . ? C56 C61 C60 119.9(3) . . ? C56 C61 Bi2 116.4(3) . . ? C60 C61 Bi2 123.7(3) . . ? O4 C62 O3 122.9(3) . . ? O4 C62 C63 121.7(3) . . ? O3 C62 C63 115.4(3) . . ? C62 C63 C64 114.7(3) . . ? C62 C63 H63A 108.6 . . ? C64 C63 H63A 108.6 . . ? C62 C63 H63B 108.6 . . ? C64 C63 H63B 108.6 . . ? H63A C63 H63B 107.6 . . ? C63 C64 Ge2 113.4(2) . . ? C63 C64 H64A 108.9 . . ? Ge2 C64 H64A 108.9 . . ? C63 C64 H64B 108.9 . . ? Ge2 C64 H64B 108.9 . . ? H64A C64 H64B 107.7 . . ? C70 C65 C66 118.3(3) . . ? C70 C65 Ge2 121.8(3) . . ? C66 C65 Ge2 119.9(3) . . ? C65 C66 C67 120.9(4) . . ? C65 C66 H66A 119.6 . . ? C67 C66 H66A 119.6 . . ? C68 C67 C66 120.1(4) . . ? C68 C67 H67A 119.9 . . ? C66 C67 H67A 119.9 . . ? C69 C68 C67 119.7(4) . . ? C69 C68 H68A 120.2 . . ? C67 C68 H68A 120.2 . . ? C68 C69 C70 120.1(4) . . ? C68 C69 H69A 119.9 . . ? C70 C69 H69A 119.9 . . ? C65 C70 C69 120.9(4) . . ? C65 C70 H70A 119.6 . . ? C69 C70 H70A 119.6 . . ? C72 C71 C76 118.0(4) . . ? C72 C71 Ge2 121.4(3) . . ? C76 C71 Ge2 120.3(3) . . ? C73 C72 C71 121.5(4) . . ? C73 C72 H72A 119.3 . . ? C71 C72 H72A 119.3 . . ? C72 C73 C74 120.1(4) . . ? C72 C73 H73A 120.0 . . ? C74 C73 H73A 120.0 . . ? C73 C74 C75 119.6(4) . . ? C73 C74 H74A 120.2 . . ? C75 C74 H74A 120.2 . . ? C74 C75 C76 120.4(4) . . ? C74 C75 H75A 119.8 . . ? C76 C75 H75A 119.8 . . ? C75 C76 C71 120.3(4) . . ? C75 C76 H76A 119.8 . . ? C71 C76 H76A 119.8 . . ? C78 C77 C82 118.1(3) . . ? C78 C77 Ge2 122.3(3) . . ? C82 C77 Ge2 119.5(3) . . ? C77 C78 C79 120.9(4) . . ? C77 C78 H78A 119.5 . . ? C79 C78 H78A 119.5 . . ? C80 C79 C78 119.8(4) . . ? C80 C79 H79A 120.1 . . ? C78 C79 H79A 120.1 . . ? C81 C80 C79 120.0(4) . . ? C81 C80 H80A 120.0 . . ? C79 C80 H80A 120.0 . . ? C80 C81 C82 120.5(4) . . ? C80 C81 H81A 119.8 . . ? C82 C81 H81A 119.8 . . ? C81 C82 C77 120.7(4) . . ? C81 C82 H82A 119.7 . . ? C77 C82 H82A 119.7 . . ? C30 Ge1 C24 111.72(14) . . ? C30 Ge1 C36 109.61(14) . . ? C24 Ge1 C36 108.83(14) . . ? C30 Ge1 C23 110.54(15) . . ? C24 Ge1 C23 109.08(14) . . ? C36 Ge1 C23 106.92(14) . . ? C64 Ge2 C65 110.81(15) . . ? C64 Ge2 C77 109.69(15) . . ? C65 Ge2 C77 110.82(14) . . ? C64 Ge2 C71 107.21(15) . . ? C65 Ge2 C71 109.18(15) . . ? C77 Ge2 C71 109.04(15) . . ? C7 N1 C14 110.0(3) . . ? C7 N1 C8 114.7(3) . . ? C14 N1 C8 111.2(3) . . ? C7 N1 Bi1 106.40(19) . . ? C14 N1 Bi1 102.68(19) . . ? C8 N1 Bi1 111.1(2) . . ? C55 N2 C48 109.5(3) . . ? C55 N2 C49 111.3(3) . . ? C48 N2 C49 114.6(3) . . ? C55 N2 Bi2 103.3(2) . . ? C48 N2 Bi2 106.65(19) . . ? C49 N2 Bi2 110.77(19) . . ? C21 O1 Bi1 111.9(2) . . ? C62 O3 Bi2 111.4(2) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.768 _refine_diff_density_min -1.907 _refine_diff_density_rms 0.105 # Attachment 'CCDC 728508.cif' data_cd29137 _database_code_depnum_ccdc_archive 'CCDC 728508' _audit_update_record ; 2009-06-04 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Bi Cl O5 S' _chemical_formula_weight 538.74 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' Cl Cl 0.1484 0.1585 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8231(17) _cell_length_b 11.7666(14) _cell_length_c 10.0447(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.639(2) _cell_angle_gamma 90.00 _cell_volume 1632.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3348 _cell_measurement_theta_min 4.548 _cell_measurement_theta_max 51.984 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.186 _exptl_crystal_size_mid 0.173 _exptl_crystal_size_min 0.168 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 11.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.63284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8802 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3206 _reflns_number_gt 2641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0805P)^2^+3.7674P] 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 3206 _refine_ls_number_parameters 207 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.007 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 Bi 0.26420(3) -0.03829(3) 1.02691(4) 0.0433(2) Uani 1 1 d . . . S1 S 0.2822(2) 0.1526(3) 1.1738(3) 0.0586(8) Uani 1 1 d . . . Cl1 Cl 0.2440(3) -0.0597(3) 0.4736(3) 0.0601(8) Uani 1 1 d . . . O1 O 0.2449(9) -0.1603(8) 0.8258(9) 0.073(3) Uani 1 1 d D . . O2 O 0.182(2) 0.0295(19) 0.484(3) 0.172(11) Uani 1 1 d . . . O3 O 0.3381(14) -0.015(2) 0.504(2) 0.165(8) Uani 1 1 d . . . O4 O 0.2405(11) -0.1019(13) 0.3420(11) 0.107(4) Uani 1 1 d . . . O5 O 0.2283(18) -0.1558(13) 0.5563(15) 0.140(9) Uani 1 1 d . . . C1 C 0.3778(8) 0.0583(10) 0.9171(12) 0.050(3) Uani 1 1 d . . . C2 C 0.4320(9) 0.0067(12) 0.8272(13) 0.054(3) Uani 1 1 d . . . H2 H 0.4198 -0.0686 0.8037 0.065 Uiso 1 1 calc R . . C3 C 0.5048(10) 0.0650(15) 0.7704(16) 0.073(4) Uani 1 1 d . . . H3 H 0.5404 0.0289 0.7065 0.087 Uiso 1 1 calc R . . C4 C 0.5273(9) 0.1759(13) 0.8046(16) 0.071(4) Uani 1 1 d . . . H4 H 0.5781 0.2136 0.7662 0.085 Uiso 1 1 calc R . . C5 C 0.4731(10) 0.2286(12) 0.8960(15) 0.067(4) Uani 1 1 d . . . H5 H 0.4872 0.3031 0.9209 0.080 Uiso 1 1 calc R . . C6 C 0.3961(8) 0.1713(10) 0.9530(12) 0.051(3) Uani 1 1 d . . . C7 C 0.3334(10) 0.2367(10) 1.0428(14) 0.067(4) Uani 1 1 d . . . H7A H 0.2809 0.2709 0.9893 0.080 Uiso 1 1 calc R . . H7B H 0.3714 0.2978 1.0835 0.080 Uiso 1 1 calc R . . C8 C 0.1355(8) 0.0664(9) 0.9529(12) 0.046(3) Uani 1 1 d . . . C9 C 0.0806(9) 0.0305(12) 0.8402(14) 0.064(4) Uani 1 1 d . . . H9 H 0.0981 -0.0356 0.7966 0.076 Uiso 1 1 calc R . . C10 C 0.0004(10) 0.0918(13) 0.7921(15) 0.066(3) Uani 1 1 d . . . H10 H -0.0337 0.0696 0.7144 0.079 Uiso 1 1 calc R . . C11 C -0.0277(9) 0.1860(15) 0.8621(17) 0.082(5) Uani 1 1 d . . . H11 H -0.0832 0.2257 0.8340 0.098 Uiso 1 1 calc R . . C12 C 0.0261(10) 0.2220(12) 0.9736(16) 0.070(4) Uani 1 1 d . . . H12 H 0.0096 0.2887 1.0168 0.085 Uiso 1 1 calc R . . C13 C 0.1067(9) 0.1565(12) 1.0223(13) 0.061(3) Uani 1 1 d . . . C14 C 0.1534(10) 0.1933(14) 1.1549(15) 0.075(4) Uani 1 1 d . . . H14A H 0.1185 0.1592 1.2264 0.090 Uiso 1 1 calc R . . H14B H 0.1480 0.2752 1.1630 0.090 Uiso 1 1 calc R . . H1A H 0.249(6) -0.228(3) 0.845(8) 0.06(2) Uiso 1 1 d D . . H1B H 0.240(14) -0.168(8) 0.743(2) 0.12(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.0507(3) 0.0422(3) 0.0366(3) 0.00613(16) -0.00156(17) -0.00159(17) S1 0.0656(19) 0.0604(18) 0.0491(16) -0.0009(14) -0.0043(14) 0.0053(15) Cl1 0.088(2) 0.0495(17) 0.0433(16) -0.0013(12) 0.0073(15) -0.0084(15) O1 0.125(8) 0.051(5) 0.041(5) 0.001(4) -0.003(5) -0.018(5) O2 0.17(2) 0.16(2) 0.21(3) -0.077(17) 0.036(19) 0.048(15) O3 0.118(14) 0.189(18) 0.18(2) -0.043(15) -0.058(13) -0.038(12) O4 0.149(11) 0.123(10) 0.050(6) -0.002(6) 0.003(6) -0.009(9) O5 0.24(3) 0.090(10) 0.073(9) -0.012(7) 0.054(13) -0.032(13) C1 0.040(6) 0.062(7) 0.046(6) 0.009(5) -0.005(5) -0.001(5) C2 0.057(7) 0.053(7) 0.052(7) 0.002(6) -0.001(6) 0.008(6) C3 0.052(8) 0.102(12) 0.064(9) 0.015(8) 0.004(6) 0.014(8) C4 0.044(7) 0.074(10) 0.093(11) 0.028(8) -0.006(7) -0.007(7) C5 0.059(8) 0.058(8) 0.083(10) 0.013(7) -0.009(7) -0.002(6) C6 0.043(6) 0.047(6) 0.061(7) 0.007(5) -0.017(5) -0.001(5) C7 0.077(9) 0.039(6) 0.081(9) 0.003(6) -0.025(7) 0.001(6) C8 0.046(6) 0.045(6) 0.048(6) 0.010(5) 0.018(5) 0.004(5) C9 0.048(7) 0.089(11) 0.054(8) 0.023(7) 0.002(6) -0.013(6) C10 0.054(8) 0.073(9) 0.069(9) 0.022(8) -0.004(6) -0.007(7) C11 0.035(7) 0.115(13) 0.095(12) 0.061(11) 0.006(7) 0.009(7) C12 0.059(8) 0.061(8) 0.093(11) 0.004(8) 0.018(8) 0.015(6) C13 0.047(7) 0.076(9) 0.059(7) 0.024(7) 0.006(6) -0.003(6) C14 0.067(9) 0.093(11) 0.064(9) -0.022(8) 0.003(7) 0.017(8) _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 Bi C8 2.261(11) . ? Bi C1 2.266(12) . ? Bi O1 2.483(9) . ? Bi S1 2.693(3) . ? S1 C7 1.817(15) . ? S1 C14 1.845(14) . ? Cl1 O2 1.36(2) . ? Cl1 O4 1.411(12) . ? Cl1 O3 1.422(17) . ? Cl1 O5 1.425(16) . ? O1 H1A 0.82(2) . ? O1 H1B 0.84(2) . ? C1 C2 1.344(18) . ? C1 C6 1.398(17) . ? C2 C3 1.36(2) . ? C2 H2 0.9300 . ? C3 C4 1.38(2) . ? C3 H3 0.9300 . ? C4 C5 1.36(2) . ? C4 H4 0.9300 . ? C5 C6 1.404(18) . ? C5 H5 0.9300 . ? C6 C7 1.492(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.339(18) . ? C8 C9 1.40(2) . ? C9 C10 1.391(19) . ? C9 H9 0.9300 . ? C10 C11 1.38(2) . ? C10 H10 0.9300 . ? C11 C12 1.38(2) . ? C11 H11 0.9300 . ? C12 C13 1.422(18) . ? C12 H12 0.9300 . ? C13 C14 1.52(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 C8 Bi C1 96.8(4) . . ? C8 Bi O1 89.7(4) . . ? C1 Bi O1 86.8(4) . . ? C8 Bi S1 77.1(3) . . ? C1 Bi S1 78.4(3) . . ? O1 Bi S1 158.7(2) . . ? C7 S1 C14 101.0(7) . . ? C7 S1 Bi 95.0(4) . . ? C14 S1 Bi 95.5(5) . . ? O2 Cl1 O4 110.4(14) . . ? O2 Cl1 O3 105.8(16) . . ? O4 Cl1 O3 108.7(11) . . ? O2 Cl1 O5 117.0(16) . . ? O4 Cl1 O5 105.5(8) . . ? O3 Cl1 O5 109.2(15) . . ? Bi O1 H1A 111(6) . . ? Bi O1 H1B 151(7) . . ? H1A O1 H1B 97(3) . . ? Cl1 O5 H1B 130(3) . . ? C2 C1 C6 120.2(12) . . ? C2 C1 Bi 121.4(10) . . ? C6 C1 Bi 118.2(9) . . ? C1 C2 C3 119.9(14) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 122.2(15) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 118.3(13) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C4 C5 C6 120.5(13) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.9(12) . . ? C1 C6 C7 122.9(11) . . ? C5 C6 C7 118.1(12) . . ? C6 C7 S1 114.4(9) . . ? C6 C7 H7A 108.7 . . ? S1 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? S1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C13 C8 C9 119.8(12) . . ? C13 C8 Bi 120.6(9) . . ? C9 C8 Bi 119.4(9) . . ? C10 C9 C8 121.3(14) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 118.6(14) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C10 C11 C12 120.4(13) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.8(14) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C8 C13 C12 119.8(13) . . ? C8 C13 C14 123.9(12) . . ? C12 C13 C14 116.2(13) . . ? C13 C14 S1 112.7(9) . . ? C13 C14 H14A 109.1 . . ? S1 C14 H14A 109.0 . . ? C13 C14 H14B 109.1 . . ? S1 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 Bi S1 C7 -78.8(5) . . . . ? C1 Bi S1 C7 21.1(5) . . . . ? O1 Bi S1 C7 -26.0(9) . . . . ? C8 Bi S1 C14 22.8(6) . . . . ? C1 Bi S1 C14 122.7(6) . . . . ? O1 Bi S1 C14 75.6(10) . . . . ? O2 Cl1 O5 H1B -66(8) . . . . ? O4 Cl1 O5 H1B 171(8) . . . . ? O3 Cl1 O5 H1B 54(8) . . . . ? C8 Bi C1 C2 -119.4(10) . . . . ? O1 Bi C1 C2 -30.2(10) . . . . ? S1 Bi C1 C2 165.3(10) . . . . ? C8 Bi C1 C6 65.7(9) . . . . ? O1 Bi C1 C6 155.0(9) . . . . ? S1 Bi C1 C6 -9.6(8) . . . . ? C6 C1 C2 C3 -0.2(18) . . . . ? Bi C1 C2 C3 -175.0(10) . . . . ? C1 C2 C3 C4 2(2) . . . . ? C2 C3 C4 C5 -1(2) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C2 C1 C6 C5 -1.6(17) . . . . ? Bi C1 C6 C5 173.4(9) . . . . ? C2 C1 C6 C7 174.4(12) . . . . ? Bi C1 C6 C7 -10.6(15) . . . . ? C4 C5 C6 C1 1.8(19) . . . . ? C4 C5 C6 C7 -174.3(12) . . . . ? C1 C6 C7 S1 34.7(15) . . . . ? C5 C6 C7 S1 -149.3(10) . . . . ? C14 S1 C7 C6 -130.2(10) . . . . ? Bi S1 C7 C6 -33.6(9) . . . . ? C1 Bi C8 C13 -91.7(10) . . . . ? O1 Bi C8 C13 -178.5(9) . . . . ? S1 Bi C8 C13 -15.3(9) . . . . ? C1 Bi C8 C9 94.1(9) . . . . ? O1 Bi C8 C9 7.3(9) . . . . ? S1 Bi C8 C9 170.6(9) . . . . ? C13 C8 C9 C10 5.1(18) . . . . ? Bi C8 C9 C10 179.4(9) . . . . ? C8 C9 C10 C11 -3.5(19) . . . . ? C9 C10 C11 C12 3(2) . . . . ? C10 C11 C12 C13 -5(2) . . . . ? C9 C8 C13 C12 -6.4(18) . . . . ? Bi C8 C13 C12 179.5(9) . . . . ? C9 C8 C13 C14 171.9(12) . . . . ? Bi C8 C13 C14 -2.2(17) . . . . ? C11 C12 C13 C8 6(2) . . . . ? C11 C12 C13 C14 -172.2(13) . . . . ? C8 C13 C14 S1 27.9(18) . . . . ? C12 C13 C14 S1 -153.8(10) . . . . ? C7 S1 C14 C13 64.5(12) . . . . ? Bi S1 C14 C13 -31.7(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O5 0.84(2) 1.88(3) 2.706(17) 169(9) . O1 H1A O4 0.82(2) 2.01(4) 2.804(17) 164(8) 4_556 O1 H1A O5 0.82(2) 2.55(6) 3.186(17) 135(7) 4_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.871 _refine_diff_density_min -2.337 _refine_diff_density_rms 0.266 # Formatted by publCIF data_cd29204 _database_code_depnum_ccdc_archive 'CCDC 733223' _refine_ls_abs_structure_Rogers ? #Added by publCIF _audit_update_record ; 2009-05-18 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Bi F17 O4 S2' _chemical_formula_weight 938.43 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.7673(17) _cell_length_b 11.7803(8) _cell_length_c 10.0588(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.8420(10) _cell_angle_gamma 90.00 _cell_volume 2907.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4671 _cell_measurement_theta_min 4.794 _cell_measurement_theta_max 45.616 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.281 _exptl_crystal_size_mid 0.167 _exptl_crystal_size_min 0.155 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 6.347 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75125 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15666 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5693 _reflns_number_gt 3957 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0794P)^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 SHELXL _refine_ls_extinction_coef 0.00055(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5693 _refine_ls_number_parameters 461 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1352 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.951 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.009 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 Bi 0.628618(13) 1.02124(3) 1.07405(3) 0.06027(16) Uani 1 1 d . . . S1 S 0.61565(10) 0.8274(2) 1.2102(2) 0.0775(7) Uani 1 1 d . . . S2 S 0.66761(11) 0.0693(2) 0.5138(3) 0.0802(7) Uani 1 1 d D . . O1 O 0.6397(4) 1.1350(6) 0.8764(8) 0.093(2) Uani 1 1 d D . . O2 O 0.6628(6) -0.0342(10) 0.452(2) 0.131(10) Uani 1 1 d . A . O3 O 0.6504(8) 0.119(3) 0.622(2) 0.141(16) Uani 0.70 1 d P A 1 O4 O 0.6448(4) 0.1331(10) 0.4095(13) 0.145(5) Uani 1 1 d . A . O3' O 0.6563(12) 0.0199(18) 0.643(2) 0.076(7) Uani 0.30 1 d P A 2 C1 C 0.7036(3) 0.9232(7) 1.0449(7) 0.0583(19) Uani 1 1 d . . . C2 C 0.7381(4) 0.9618(7) 0.9571(9) 0.067(2) Uani 1 1 d . . . H2 H 0.7288 1.0266 0.9062 0.080 Uiso 1 1 calc R . . C3 C 0.7859(3) 0.9060(11) 0.9440(10) 0.085(3) Uani 1 1 d . . . H3 H 0.8089 0.9321 0.8848 0.102 Uiso 1 1 calc R . . C4 C 0.7987(4) 0.8121(11) 1.0196(11) 0.091(3) Uani 1 1 d . . . H4 H 0.8307 0.7732 1.0106 0.109 Uiso 1 1 calc R . . C5 C 0.7660(4) 0.7726(9) 1.1092(11) 0.087(3) Uani 1 1 d . . . H5 H 0.7761 0.7088 1.1611 0.104 Uiso 1 1 calc R . . C6 C 0.7191(3) 0.8270(8) 1.1215(8) 0.070(2) Uani 1 1 d . . . C7 C 0.6852(4) 0.7829(9) 1.2290(10) 0.085(3) Uani 1 1 d . . . H7A H 0.7028 0.8075 1.3164 0.102 Uiso 1 1 calc R . . H7B H 0.6861 0.7006 1.2281 0.102 Uiso 1 1 calc R . . C8 C 0.5657(3) 0.9279(7) 0.9349(8) 0.0572(18) Uani 1 1 d . . . C9 C 0.5340(4) 0.9834(8) 0.8323(10) 0.070(2) Uani 1 1 d . . . H9 H 0.5417 1.0588 0.8151 0.084 Uiso 1 1 calc R . . C10 C 0.4904(4) 0.9301(12) 0.7525(11) 0.089(3) Uani 1 1 d . . . H10 H 0.4710 0.9680 0.6801 0.106 Uiso 1 1 calc R . . C11 C 0.4771(4) 0.8237(10) 0.7821(11) 0.085(3) Uani 1 1 d . . . H11 H 0.4471 0.7885 0.7330 0.102 Uiso 1 1 calc R . . C12 C 0.5074(4) 0.7673(8) 0.8841(12) 0.083(3) Uani 1 1 d . . . H12 H 0.4981 0.6930 0.9024 0.100 Uiso 1 1 calc R . . C13 C 0.5523(3) 0.8172(7) 0.9629(8) 0.063(2) Uani 1 1 d . . . C14 C 0.5877(3) 0.7465(8) 1.0658(9) 0.075(2) Uani 1 1 d . . . H14A H 0.6174 0.7139 1.0245 0.090 Uiso 1 1 calc R . . H14B H 0.5663 0.6845 1.0943 0.090 Uiso 1 1 calc R . . C15 C 0.7382(5) 0.1101(12) 0.5375(11) 0.121(4) Uani 1 1 d D A . C16 C 0.7714(4) 0.0901(8) 0.4245(10) 0.101(3) Uani 1 1 d D . . C17 C 0.8299(5) 0.1251(11) 0.4391(12) 0.121(4) Uani 1 1 d D A . C18 C 0.8657(5) 0.1008(11) 0.3371(12) 0.111(4) Uani 1 1 d D . . C19 C 0.9229(6) 0.1454(18) 0.3490(17) 0.161(14) Uani 1 1 d D A . C20 C 0.9595(5) 0.0992(15) 0.2543(16) 0.159(7) Uani 1 1 d D . . C21 C 1.0156(9) 0.152(2) 0.273(2) 0.243(12) Uiso 1 1 d D A . C22 C 1.0555(9) 0.125(2) 0.181(2) 0.247(13) Uiso 1 1 d D . . F1 F 0.7418(6) 0.2208(14) 0.567(2) 0.160(11) Uani 0.60 1 d PD A 1 F2 F 0.7624(6) 0.063(2) 0.6490(13) 0.142(12) Uani 0.60 1 d PD A 1 F3 F 0.7426(9) 0.112(3) 0.3093(15) 0.164(14) Uani 0.60 1 d PD A 1 F4 F 0.7734(18) -0.0231(15) 0.421(6) 0.171(3) Uani 0.60 1 d PD A 1 F5 F 0.8278(6) 0.2443(9) 0.424(2) 0.175(7) Uani 0.60 1 d PD A 1 F6 F 0.8545(6) 0.109(2) 0.5638(11) 0.149(6) Uani 0.60 1 d PD A 1 F7 F 0.8376(8) 0.1142(19) 0.2186(14) 0.138(7) Uani 0.60 1 d PD A 1 F8 F 0.8784(11) -0.0137(12) 0.366(3) 0.168(10) Uani 0.60 1 d PD A 1 F9 F 0.9068(12) 0.2511(17) 0.305(3) 0.211(9) Uiso 0.60 1 d PD A 1 F10 F 0.9419(10) 0.096(3) 0.463(2) 0.243(12) Uiso 0.60 1 d PD A 1 F11 F 0.9379(12) 0.151(3) 0.138(2) 0.273(14) Uiso 0.60 1 d PD A 1 F12 F 0.9541(16) -0.008(2) 0.199(4) 0.245(15) Uiso 0.50 1 d PD A 1 F13 F 1.0024(8) 0.258(2) 0.217(2) 0.222(9) Uiso 0.60 1 d PD A 1 F14 F 1.0425(7) 0.1503(19) 0.3983(17) 0.165(5) Uiso 0.60 1 d PD A 1 F15 F 1.0274(14) 0.160(3) 0.068(3) 0.218(18) Uiso 0.60 1 d PD A 1 F16 F 1.1025(8) 0.162(2) 0.193(2) 0.203(8) Uiso 0.60 1 d PD A 1 F17 F 1.0637(12) 0.015(2) 0.177(3) 0.226(10) Uiso 0.60 1 d PD A 1 F1' F 0.7321(18) 0.222(2) 0.570(7) 0.221(4) Uiso 0.40 1 d PD A 2 F2' F 0.7733(19) 0.059(5) 0.631(5) 0.261(3) Uiso 0.40 1 d PD A 2 F3' F 0.7499(11) 0.173(3) 0.339(3) 0.157(14) Uani 0.40 1 d PD A 2 F4' F 0.7643(10) -0.0134(18) 0.376(3) 0.117(11) Uani 0.40 1 d PD A 2 F5' F 0.8480(13) 0.192(3) 0.535(3) 0.168(12) Uiso 0.40 1 d PD A 2 F6' F 0.8480(13) 0.030(2) 0.516(3) 0.165(10) Uiso 0.40 1 d PD A 2 F7' F 0.8509(10) 0.213(2) 0.290(3) 0.165(12) Uiso 0.40 1 d PD A 2 F8' F 0.8444(17) 0.033(5) 0.241(5) 0.171(3) Uani 0.40 1 d PD A 2 F9' F 0.936(2) 0.2512(18) 0.305(5) 0.222(3) Uiso 0.40 1 d PD A 2 F10' F 0.9436(7) 0.1611(17) 0.4725(15) 0.091(4) Uiso 0.40 1 d PD A 2 F11' F 0.9339(7) 0.0906(18) 0.1290(15) 0.097(5) Uiso 0.40 1 d PD A 2 F12' F 0.9745(9) -0.0034(15) 0.313(2) 0.171(7) Uiso 0.50 1 d PD A 2 F13' F 1.0297(13) 0.249(3) 0.339(4) 0.215(12) Uiso 0.40 1 d PD A 2 F14' F 1.032(2) 0.059(4) 0.353(5) 0.223(2) Uiso 0.40 1 d PD A 2 F17' F 1.0407(10) 0.101(3) 0.057(2) 0.149(8) Uiso 0.40 1 d PD A 2 F16' F 1.0946(13) 0.098(4) 0.277(3) 0.242(15) Uiso 0.40 1 d PD A 2 F15' F 1.0695(15) 0.236(3) 0.180(4) 0.239(15) Uiso 0.40 1 d PD A 2 H1B H 0.665(9) 1.11(3) 0.84(3) 0.14(19) Uiso 1 1 d D . . H1A H 0.642(4) 1.2040(19) 0.877(11) 0.12(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.0705(2) 0.0613(2) 0.0506(2) -0.01289(14) 0.01411(14) 0.00077(14) S1 0.0863(15) 0.0921(17) 0.0603(13) 0.0152(12) 0.0320(12) 0.0048(13) S2 0.1040(18) 0.0716(16) 0.0663(14) 0.0057(12) 0.0168(13) 0.0041(14) O1 0.133(6) 0.060(4) 0.086(5) 0.005(4) 0.020(4) -0.015(4) O2 0.103(11) 0.103(10) 0.201(3) -0.050(13) 0.116(16) -0.068(8) O3 0.083(15) 0.232(4) 0.106(15) -0.082(2) -0.002(12) 0.081(2) O4 0.105(7) 0.129(10) 0.180(12) 0.100(9) -0.044(8) -0.034(7) O3' 0.131(2) 0.068(13) 0.034(10) -0.019(10) 0.023(12) 0.008(13) C1 0.062(4) 0.067(5) 0.047(4) -0.005(4) 0.009(4) 0.000(4) C2 0.070(5) 0.067(6) 0.064(5) -0.005(4) 0.014(4) -0.011(4) C3 0.056(5) 0.112(9) 0.090(7) -0.007(6) 0.022(5) 0.001(5) C4 0.062(6) 0.120(9) 0.095(8) 0.002(7) 0.026(5) 0.017(6) C5 0.074(6) 0.090(7) 0.099(8) 0.009(6) 0.021(6) 0.018(5) C6 0.068(5) 0.084(6) 0.058(5) 0.003(5) 0.012(4) -0.008(5) C7 0.111(7) 0.081(7) 0.066(6) 0.019(5) 0.022(5) 0.010(6) C8 0.051(4) 0.067(5) 0.057(5) -0.010(4) 0.018(4) 0.002(4) C9 0.065(5) 0.069(5) 0.076(6) -0.009(5) 0.012(5) 0.004(4) C10 0.074(6) 0.105(8) 0.083(7) -0.020(6) -0.002(5) 0.022(6) C11 0.060(5) 0.083(7) 0.108(8) -0.030(6) -0.002(5) 0.006(5) C12 0.069(5) 0.060(6) 0.125(9) -0.031(6) 0.028(6) -0.007(4) C13 0.061(5) 0.064(5) 0.070(5) -0.010(4) 0.031(4) 0.001(4) C14 0.075(5) 0.069(6) 0.089(6) 0.009(5) 0.035(5) 0.001(4) C15 0.139(11) 0.147(14) 0.070(7) 0.002(8) -0.010(8) 0.008(10) C16 0.124(8) 0.102(9) 0.087(7) 0.021(6) 0.023(6) -0.011(6) C17 0.127(11) 0.123(12) 0.107(10) 0.010(8) -0.002(9) 0.014(9) C18 0.118(10) 0.113(11) 0.106(10) 0.006(8) 0.028(8) -0.005(8) C19 0.115(13) 0.242(3) 0.152(3) 0.102(2) 0.067(15) 0.072(17) C20 0.092(9) 0.192(19) 0.192(18) 0.083(16) 0.017(11) -0.001(10) F1 0.090(7) 0.145(14) 0.241(2) -0.151(16) 0.006(9) -0.030(7) F2 0.078(7) 0.291(4) 0.046(6) 0.088(11) -0.007(5) 0.013(11) F3 0.167(16) 0.271(4) 0.044(7) 0.007(13) -0.007(8) -0.12(2) F4 0.201(4) 0.106(18) 0.221(8) -0.101(3) 0.011(4) 0.009(18) F5 0.165(12) 0.055(7) 0.301(2) -0.032(10) 0.031(14) 0.005(7) F6 0.144(11) 0.22(2) 0.065(7) -0.031(10) -0.043(7) 0.006(12) F7 0.146(12) 0.195(19) 0.065(8) -0.006(9) -0.020(8) -0.029(13) F8 0.231(3) 0.070(9) 0.211(2) 0.018(11) 0.112(2) 0.015(11) F3' 0.102(15) 0.211(3) 0.151(3) 0.131(2) -0.009(14) 0.025(18) F4' 0.121(15) 0.13(2) 0.116(15) -0.084(14) 0.086(14) -0.082(15) F8' 0.131(3) 0.221(6) 0.181(5) -0.171(5) 0.121(3) -0.111(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 Bi C8 2.236(8) . ? Bi C1 2.240(8) . ? Bi O1 2.445(7) . ? Bi S1 2.704(2) . ? S1 C7 1.787(10) . ? S1 C14 1.795(10) . ? S2 O3 1.351(15) . ? S2 O4 1.349(10) . ? S2 O2 1.365(13) . ? S2 O3' 1.48(2) . ? S2 C15 1.797(14) . ? O1 H1B 0.83(5) . ? O1 H1A 0.81(2) . ? C1 C2 1.388(11) . ? C1 C6 1.394(12) . ? C2 C3 1.376(13) . ? C2 H2 0.9300 . ? C3 C4 1.355(15) . ? C3 H3 0.9300 . ? C4 C5 1.374(13) . ? C4 H4 0.9300 . ? C5 C6 1.346(12) . ? C5 H5 0.9300 . ? C6 C7 1.546(12) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.375(12) . ? C8 C13 1.384(12) . ? C9 C10 1.404(14) . ? C9 H9 0.9300 . ? C10 C11 1.339(15) . ? C10 H10 0.9300 . ? C11 C12 1.360(14) . ? C11 H11 0.9300 . ? C12 C13 1.403(12) . ? C12 H12 0.9300 . ? C13 C14 1.513(12) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 F2 1.320(13) . ? C15 F2' 1.34(2) . ? C15 F1 1.338(15) . ? C15 F1' 1.37(2) . ? C15 C16 1.511(13) . ? C16 F3 1.301(15) . ? C16 F4' 1.316(16) . ? C16 F4 1.335(17) . ? C16 F3' 1.359(16) . ? C16 C17 1.493(13) . ? C17 F5' 1.283(18) . ? C17 F6 1.331(14) . ? C17 F6' 1.401(18) . ? C17 F5 1.413(14) . ? C17 C18 1.472(13) . ? C18 F8' 1.302(17) . ? C18 F7 1.305(14) . ? C18 F8 1.407(15) . ? C18 F7' 1.439(17) . ? C18 C19 1.502(15) . ? C19 F10' 1.291(16) . ? C19 F10 1.316(17) . ? C19 F9 1.365(17) . ? C19 F9' 1.38(2) . ? C19 C20 1.504(16) . ? C20 F11' 1.335(16) . ? C20 F11 1.361(18) . ? C20 F12' 1.374(16) . ? C20 F12 1.378(18) . ? C20 C21 1.508(16) . ? C21 F14 1.344(17) . ? C21 F13' 1.350(19) . ? C21 F14' 1.39(2) . ? C21 F13 1.395(18) . ? C21 C22 1.476(18) . ? C22 F16 1.232(18) . ? C22 F17' 1.276(18) . ? C22 F16' 1.312(19) . ? C22 F15 1.311(19) . ? C22 F17 1.311(18) . ? C22 F15' 1.354(19) . ? F12' F14' 1.61(5) . ? 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 C8 Bi C1 100.6(3) . . ? C8 Bi O1 84.7(3) . . ? C1 Bi O1 89.4(3) . . ? C8 Bi S1 77.3(2) . . ? C1 Bi S1 77.8(2) . . ? O1 Bi S1 155.42(19) . . ? C7 S1 C14 100.9(5) . . ? C7 S1 Bi 97.0(3) . . ? C14 S1 Bi 95.6(3) . . ? O3 S2 O4 103.9(14) . . ? O3 S2 O2 137.1(18) . . ? O4 S2 O2 98.2(12) . . ? O3 S2 O3' 49.4(14) . . ? O4 S2 O3' 142.2(13) . . ? O2 S2 O3' 91.8(12) . . ? O3 S2 C15 100.6(12) . . ? O4 S2 C15 104.5(6) . . ? O2 S2 C15 108.8(7) . . ? O3' S2 C15 106.6(12) . . ? Bi O1 H1B 108(10) . . ? Bi O1 H1A 124(8) . . ? H1B O1 H1A 109(10) . . ? C2 C1 C6 118.1(8) . . ? C2 C1 Bi 120.5(6) . . ? C6 C1 Bi 121.1(6) . . ? C3 C2 C1 121.1(9) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 118.4(9) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 122.0(9) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 119.5(10) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 120.8(8) . . ? C5 C6 C7 117.4(9) . . ? C1 C6 C7 121.7(8) . . ? C6 C7 S1 115.7(6) . . ? C6 C7 H7A 108.4 . . ? S1 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? S1 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C13 118.2(8) . . ? C9 C8 Bi 120.9(6) . . ? C13 C8 Bi 120.2(6) . . ? C8 C9 C10 122.2(10) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 119.0(10) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 119.8(9) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 122.4(9) . . ? C11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C8 C13 C12 118.3(9) . . ? C8 C13 C14 121.7(8) . . ? C12 C13 C14 119.8(8) . . ? C13 C14 S1 112.6(6) . . ? C13 C14 H14A 109.1 . . ? S1 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? S1 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? F2 C15 F2' 15(3) . . ? F2 C15 F1 102.4(18) . . ? F2' C15 F1 106(3) . . ? F2 C15 F1' 105(3) . . ? F2' C15 F1' 110(4) . . ? F1 C15 F1' 10(2) . . ? F2 C15 C16 110.1(12) . . ? F2' C15 C16 95(3) . . ? F1 C15 C16 106.9(13) . . ? F1' C15 C16 115(3) . . ? F2 C15 S2 108.7(11) . . ? F2' C15 S2 120(3) . . ? F1 C15 S2 108.9(10) . . ? F1' C15 S2 99(2) . . ? C16 C15 S2 118.6(8) . . ? F3 C16 F4' 79.9(19) . . ? F3 C16 F4 101(3) . . ? F4' C16 F4 21(3) . . ? F3 C16 F3' 34.4(19) . . ? F4' C16 F3' 114(2) . . ? F4 C16 F3' 135(3) . . ? F3 C16 C17 116.1(13) . . ? F4' C16 C17 111.7(13) . . ? F4 C16 C17 104(2) . . ? F3' C16 C17 98.9(14) . . ? F3 C16 C15 110.5(14) . . ? F4' C16 C15 111.4(11) . . ? F4 C16 C15 102(2) . . ? F3' C16 C15 99.1(16) . . ? C17 C16 C15 120.2(10) . . ? F5' C17 F6 46.1(16) . . ? F5' C17 F6' 91(2) . . ? F6 C17 F6' 45.2(13) . . ? F5' C17 F5 58.3(17) . . ? F6 C17 F5 104.4(16) . . ? F6' C17 F5 149(2) . . ? F5' C17 C18 117.6(18) . . ? F6 C17 C18 112.7(12) . . ? F6' C17 C18 93.0(17) . . ? F5 C17 C18 97.6(11) . . ? F5' C17 C16 118.6(18) . . ? F6 C17 C16 111.6(12) . . ? F6' C17 C16 93.8(16) . . ? F5 C17 C16 104.0(11) . . ? C18 C17 C16 123.1(11) . . ? F8' C18 F7 45(3) . . ? F8' C18 F8 68(3) . . ? F7 C18 F8 112.2(18) . . ? F8' C18 F7' 105(4) . . ? F7 C18 F7' 60.4(16) . . ? F8 C18 F7' 172(2) . . ? F8' C18 C17 114.3(17) . . ? F7 C18 C17 108.5(13) . . ? F8 C18 C17 100.6(13) . . ? F7' C18 C17 84.4(11) . . ? F8' C18 C19 123.7(19) . . ? F7 C18 C19 114.2(13) . . ? F8 C18 C19 97.8(15) . . ? F7' C18 C19 84.2(11) . . ? C17 C18 C19 121.9(12) . . ? F10' C19 F10 34.7(15) . . ? F10' C19 F9 104(2) . . ? F10 C19 F9 138(3) . . ? F10' C19 F9' 96(3) . . ? F10 C19 F9' 128(3) . . ? F9 C19 F9' 31(3) . . ? F10' C19 C18 111.9(14) . . ? F10 C19 C18 97.8(16) . . ? F9 C19 C18 93.5(14) . . ? F9' C19 C18 124(3) . . ? F10' C19 C20 117.8(13) . . ? F10 C19 C20 102.5(17) . . ? F9 C19 C20 107.4(17) . . ? F9' C19 C20 86.1(13) . . ? C18 C19 C20 117.9(15) . . ? F11' C20 F11 30.9(16) . . ? F11' C20 F12' 113.9(18) . . ? F11 C20 F12' 144(2) . . ? F11' C20 F12 63(2) . . ? F11 C20 F12 93(3) . . ? F12' C20 F12 51.2(17) . . ? F11' C20 C21 117.3(15) . . ? F11 C20 C21 99.9(18) . . ? F12' C20 C21 96.7(16) . . ? F12 C20 C21 117(2) . . ? F11' C20 C19 112.0(13) . . ? F11 C20 C19 100.5(17) . . ? F12' C20 C19 101.4(15) . . ? F12 C20 C19 124(2) . . ? C21 C20 C19 113.5(16) . . ? F14 C21 F13' 59.1(18) . . ? F14 C21 F14' 51(2) . . ? F13' C21 F14' 111(3) . . ? F14 C21 F13 116(2) . . ? F13' C21 F13 57.3(18) . . ? F14' C21 F13 168(3) . . ? F14 C21 C22 107.4(19) . . ? F13' C21 C22 110(2) . . ? F14' C21 C22 91(3) . . ? F13 C21 C22 94.5(17) . . ? F14 C21 C20 116.2(17) . . ? F13' C21 C20 126(3) . . ? F14' C21 C20 87(3) . . ? F13 C21 C20 99.0(19) . . ? C22 C21 C20 121.3(19) . . ? F16 C22 F17' 109(3) . . ? F16 C22 F16' 54(2) . . ? F17' C22 F16' 138(3) . . ? F16 C22 F15 111(3) . . ? F17' C22 F15 35(2) . . ? F16' C22 F15 165(4) . . ? F16 C22 F17 101(2) . . ? F17' C22 F17 77(2) . . ? F16' C22 F17 71(2) . . ? F15 C22 F17 111(3) . . ? F16 C22 F15' 55(2) . . ? F17' C22 F15' 104(3) . . ? F16' C22 F15' 94(3) . . ? F15 C22 F15' 78(3) . . ? F17 C22 F15' 156(3) . . ? F16 C22 C21 125(2) . . ? F17' C22 C21 122(2) . . ? F16' C22 C21 94(3) . . ? F15 C22 C21 99(2) . . ? F17 C22 C21 110(3) . . ? F15' C22 C21 89.7(15) . . ? C20 F12' F14' 83.4(17) . . ? C21 F14' F12' 92(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 Bi S1 C7 123.1(4) . . . . ? C1 Bi S1 C7 19.1(4) . . . . ? O1 Bi S1 C7 79.1(6) . . . . ? C8 Bi S1 C14 21.3(3) . . . . ? C1 Bi S1 C14 -82.6(3) . . . . ? O1 Bi S1 C14 -22.6(6) . . . . ? C8 Bi C1 C2 97.3(7) . . . . ? O1 Bi C1 C2 12.8(6) . . . . ? S1 Bi C1 C2 171.7(7) . . . . ? C8 Bi C1 C6 -87.7(7) . . . . ? O1 Bi C1 C6 -172.2(7) . . . . ? S1 Bi C1 C6 -13.3(6) . . . . ? C6 C1 C2 C3 1.1(13) . . . . ? Bi C1 C2 C3 176.2(7) . . . . ? C1 C2 C3 C4 -0.3(15) . . . . ? C2 C3 C4 C5 -0.9(17) . . . . ? C3 C4 C5 C6 1.2(18) . . . . ? C4 C5 C6 C1 -0.3(16) . . . . ? C4 C5 C6 C7 -176.8(10) . . . . ? C2 C1 C6 C5 -0.8(13) . . . . ? Bi C1 C6 C5 -175.9(8) . . . . ? C2 C1 C6 C7 175.6(8) . . . . ? Bi C1 C6 C7 0.5(12) . . . . ? C5 C6 C7 S1 -162.2(8) . . . . ? C1 C6 C7 S1 21.3(12) . . . . ? C14 S1 C7 C6 71.3(8) . . . . ? Bi S1 C7 C6 -25.9(8) . . . . ? C1 Bi C8 C9 -122.4(6) . . . . ? O1 Bi C8 C9 -34.0(6) . . . . ? S1 Bi C8 C9 162.8(6) . . . . ? C1 Bi C8 C13 67.5(6) . . . . ? O1 Bi C8 C13 155.9(6) . . . . ? S1 Bi C8 C13 -7.3(5) . . . . ? C13 C8 C9 C10 -2.7(13) . . . . ? Bi C8 C9 C10 -173.0(7) . . . . ? C8 C9 C10 C11 4.0(14) . . . . ? C9 C10 C11 C12 -3.2(15) . . . . ? C10 C11 C12 C13 1.2(15) . . . . ? C9 C8 C13 C12 0.7(11) . . . . ? Bi C8 C13 C12 171.0(6) . . . . ? C9 C8 C13 C14 174.6(7) . . . . ? Bi C8 C13 C14 -15.1(9) . . . . ? C11 C12 C13 C8 0.1(12) . . . . ? C11 C12 C13 C14 -174.0(8) . . . . ? C8 C13 C14 S1 38.6(9) . . . . ? C12 C13 C14 S1 -147.6(6) . . . . ? C7 S1 C14 C13 -133.4(6) . . . . ? Bi S1 C14 C13 -35.1(6) . . . . ? O3 S2 C15 F2 64(2) . . . . ? O4 S2 C15 F2 171.8(16) . . . . ? O2 S2 C15 F2 -84.1(18) . . . . ? O3' S2 C15 F2 13.7(17) . . . . ? O3 S2 C15 F2' 75(4) . . . . ? O4 S2 C15 F2' -177(3) . . . . ? O2 S2 C15 F2' -73(4) . . . . ? O3' S2 C15 F2' 25(4) . . . . ? O3 S2 C15 F1 -47(2) . . . . ? O4 S2 C15 F1 61.0(15) . . . . ? O2 S2 C15 F1 165.1(16) . . . . ? O3' S2 C15 F1 -97.1(16) . . . . ? O3 S2 C15 F1' -44(4) . . . . ? O4 S2 C15 F1' 63(3) . . . . ? O2 S2 C15 F1' 167(3) . . . . ? O3' S2 C15 F1' -95(3) . . . . ? O3 S2 C15 C16 -169.0(18) . . . . ? O4 S2 C15 C16 -61.5(12) . . . . ? O2 S2 C15 C16 42.6(14) . . . . ? O3' S2 C15 C16 140.3(12) . . . . ? F2 C15 C16 F3 165(2) . . . . ? F2' C15 C16 F3 167(3) . . . . ? F1 C15 C16 F3 -84.5(19) . . . . ? F1' C15 C16 F3 -77(3) . . . . ? S2 C15 C16 F3 39.0(19) . . . . ? F2 C15 C16 F4' 78(2) . . . . ? F2' C15 C16 F4' 81(3) . . . . ? F1 C15 C16 F4' -171(2) . . . . ? F1' C15 C16 F4' -164(3) . . . . ? S2 C15 C16 F4' -48(2) . . . . ? F2 C15 C16 F4 58(3) . . . . ? F2' C15 C16 F4 61(3) . . . . ? F1 C15 C16 F4 169(2) . . . . ? F1' C15 C16 F4 176(4) . . . . ? S2 C15 C16 F4 -68(2) . . . . ? F2 C15 C16 F3' -161(2) . . . . ? F2' C15 C16 F3' -159(3) . . . . ? F1 C15 C16 F3' -51(2) . . . . ? F1' C15 C16 F3' -44(3) . . . . ? S2 C15 C16 F3' 72.7(18) . . . . ? F2 C15 C16 C17 -55.3(18) . . . . ? F2' C15 C16 C17 -53(3) . . . . ? F1 C15 C16 C17 55.2(15) . . . . ? F1' C15 C16 C17 62(3) . . . . ? S2 C15 C16 C17 178.7(8) . . . . ? F3 C16 C17 F5' 123(3) . . . . ? F4' C16 C17 F5' -148(3) . . . . ? F4 C16 C17 F5' -127(3) . . . . ? F3' C16 C17 F5' 92(3) . . . . ? C15 C16 C17 F5' -14(3) . . . . ? F3 C16 C17 F6 174(2) . . . . ? F4' C16 C17 F6 -97(2) . . . . ? F4 C16 C17 F6 -76(3) . . . . ? F3' C16 C17 F6 143(2) . . . . ? C15 C16 C17 F6 36.5(19) . . . . ? F3 C16 C17 F6' -143(2) . . . . ? F4' C16 C17 F6' -54(2) . . . . ? F4 C16 C17 F6' -33(3) . . . . ? F3' C16 C17 F6' -175(2) . . . . ? C15 C16 C17 F6' 79(2) . . . . ? F3 C16 C17 F5 62(2) . . . . ? F4' C16 C17 F5 151.1(18) . . . . ? F4 C16 C17 F5 172(3) . . . . ? F3' C16 C17 F5 31(2) . . . . ? C15 C16 C17 F5 -75.5(15) . . . . ? F3 C16 C17 C18 -47(2) . . . . ? F4' C16 C17 C18 42(2) . . . . ? F4 C16 C17 C18 63(3) . . . . ? F3' C16 C17 C18 -78(2) . . . . ? C15 C16 C17 C18 175.5(11) . . . . ? F5' C17 C18 F8' -179(4) . . . . ? F6 C17 C18 F8' 130(4) . . . . ? F6' C17 C18 F8' 88(4) . . . . ? F5 C17 C18 F8' -121(4) . . . . ? C16 C17 C18 F8' -9(4) . . . . ? F5' C17 C18 F7 -131(2) . . . . ? F6 C17 C18 F7 177.5(18) . . . . ? F6' C17 C18 F7 136(2) . . . . ? F5 C17 C18 F7 -73.3(16) . . . . ? C16 C17 C18 F7 39.0(17) . . . . ? F5' C17 C18 F8 111(3) . . . . ? F6 C17 C18 F8 60(2) . . . . ? F6' C17 C18 F8 18(2) . . . . ? F5 C17 C18 F8 168.8(18) . . . . ? C16 C17 C18 F8 -78.9(18) . . . . ? F5' C17 C18 F7' -75(3) . . . . ? F6 C17 C18 F7' -126(2) . . . . ? F6' C17 C18 F7' -168(2) . . . . ? F5 C17 C18 F7' -17.1(17) . . . . ? C16 C17 C18 F7' 95.2(17) . . . . ? F5' C17 C18 C19 4(3) . . . . ? F6 C17 C18 C19 -47(2) . . . . ? F6' C17 C18 C19 -89(2) . . . . ? F5 C17 C18 C19 62.5(16) . . . . ? C16 C17 C18 C19 174.8(12) . . . . ? F8' C18 C19 F10' -149(4) . . . . ? F7 C18 C19 F10' 161.2(19) . . . . ? F8 C18 C19 F10' -80(2) . . . . ? F7' C18 C19 F10' 107(2) . . . . ? C17 C18 C19 F10' 28(2) . . . . ? F8' C18 C19 F10 -116(5) . . . . ? F7 C18 C19 F10 -166(2) . . . . ? F8 C18 C19 F10 -47(2) . . . . ? F7' C18 C19 F10 140(2) . . . . ? C17 C18 C19 F10 61(2) . . . . ? F8' C18 C19 F9 105(4) . . . . ? F7 C18 C19 F9 54(2) . . . . ? F8 C18 C19 F9 173.2(19) . . . . ? F7' C18 C19 F9 1(2) . . . . ? C17 C18 C19 F9 -79.2(18) . . . . ? F8' C18 C19 F9' 98(5) . . . . ? F7 C18 C19 F9' 48(3) . . . . ? F8 C18 C19 F9' 166(3) . . . . ? F7' C18 C19 F9' -6(3) . . . . ? C17 C18 C19 F9' -86(3) . . . . ? F8' C18 C19 C20 -7(5) . . . . ? F7 C18 C19 C20 -57(2) . . . . ? F8 C18 C19 C20 61.4(19) . . . . ? F7' C18 C19 C20 -111.2(18) . . . . ? C17 C18 C19 C20 169.1(12) . . . . ? F10' C19 C20 F11' -177.7(19) . . . . ? F10 C19 C20 F11' 149(2) . . . . ? F9 C19 C20 F11' -61(2) . . . . ? F9' C19 C20 F11' -83(3) . . . . ? C18 C19 C20 F11' 43(2) . . . . ? F10' C19 C20 F11 -148(2) . . . . ? F10 C19 C20 F11 179(2) . . . . ? F9 C19 C20 F11 -31(2) . . . . ? F9' C19 C20 F11 -53(3) . . . . ? C18 C19 C20 F11 73(2) . . . . ? F10' C19 C20 F12' 60(2) . . . . ? F10 C19 C20 F12' 27(2) . . . . ? F9 C19 C20 F12' 177(2) . . . . ? F9' C19 C20 F12' 155(3) . . . . ? C18 C19 C20 F12' -78.8(18) . . . . ? F10' C19 C20 F12 111(3) . . . . ? F10 C19 C20 F12 78(3) . . . . ? F9 C19 C20 F12 -132(3) . . . . ? F9' C19 C20 F12 -154(4) . . . . ? C18 C19 C20 F12 -28(3) . . . . ? F10' C19 C20 C21 -42(2) . . . . ? F10 C19 C20 C21 -75(2) . . . . ? F9 C19 C20 C21 75(2) . . . . ? F9' C19 C20 C21 53(3) . . . . ? C18 C19 C20 C21 178.7(15) . . . . ? F11' C20 C21 F14 -174(2) . . . . ? F11 C20 C21 F14 158(3) . . . . ? F12' C20 C21 F14 -53(3) . . . . ? F12 C20 C21 F14 -103(3) . . . . ? C19 C20 C21 F14 52(3) . . . . ? F11' C20 C21 F13' 116(3) . . . . ? F11 C20 C21 F13' 89(3) . . . . ? F12' C20 C21 F13' -123(3) . . . . ? F12 C20 C21 F13' -172(3) . . . . ? C19 C20 C21 F13' -17(3) . . . . ? F11' C20 C21 F14' -131(3) . . . . ? F11 C20 C21 F14' -158(3) . . . . ? F12' C20 C21 F14' -9(3) . . . . ? F12 C20 C21 F14' -59(4) . . . . ? C19 C20 C21 F14' 96(3) . . . . ? F11' C20 C21 F13 60(3) . . . . ? F11 C20 C21 F13 33(2) . . . . ? F12' C20 C21 F13 -179(2) . . . . ? F12 C20 C21 F13 132(3) . . . . ? C19 C20 C21 F13 -73(2) . . . . ? F11' C20 C21 C22 -41(3) . . . . ? F11 C20 C21 C22 -68(3) . . . . ? F12' C20 C21 C22 80(2) . . . . ? F12 C20 C21 C22 31(3) . . . . ? C19 C20 C21 C22 -174.0(19) . . . . ? F14 C21 C22 F16 -40(3) . . . . ? F13' C21 C22 F16 23(4) . . . . ? F14' C21 C22 F16 -90(4) . . . . ? F13 C21 C22 F16 79(3) . . . . ? C20 C21 C22 F16 -177(2) . . . . ? F14 C21 C22 F17' 168(3) . . . . ? F13' C21 C22 F17' -130(3) . . . . ? F14' C21 C22 F17' 118(4) . . . . ? F13 C21 C22 F17' -73(3) . . . . ? C20 C21 C22 F17' 31(4) . . . . ? F14 C21 C22 F16' 9(3) . . . . ? F13' C21 C22 F16' 71(3) . . . . ? F14' C21 C22 F16' -41(3) . . . . ? F13 C21 C22 F16' 128(3) . . . . ? C20 C21 C22 F16' -128(3) . . . . ? F14 C21 C22 F15 -163(3) . . . . ? F13' C21 C22 F15 -101(3) . . . . ? F14' C21 C22 F15 147(3) . . . . ? F13 C21 C22 F15 -44(3) . . . . ? C20 C21 C22 F15 60(3) . . . . ? F14 C21 C22 F17 81(3) . . . . ? F13' C21 C22 F17 143(3) . . . . ? F14' C21 C22 F17 31(3) . . . . ? F13 C21 C22 F17 -160(2) . . . . ? C20 C21 C22 F17 -56(3) . . . . ? F14 C21 C22 F15' -85(3) . . . . ? F13' C21 C22 F15' -23(3) . . . . ? F14' C21 C22 F15' -135(3) . . . . ? F13 C21 C22 F15' 34(2) . . . . ? C20 C21 C22 F15' 138(3) . . . . ? F11' C20 F12' F14' 132(2) . . . . ? F11 C20 F12' F14' 125(4) . . . . ? F12 C20 F12' F14' 128(3) . . . . ? C21 C20 F12' F14' 8(3) . . . . ? C19 C20 F12' F14' -108(2) . . . . ? F14 C21 F14' F12' 135(4) . . . . ? F13' C21 F14' F12' 135(3) . . . . ? F13 C21 F14' F12' 128(14) . . . . ? C22 C21 F14' F12' -113(2) . . . . ? C20 C21 F14' F12' 8(2) . . . . ? C20 F12' F14' C21 -9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.383 _refine_diff_density_min -1.425 _refine_diff_density_rms 0.163 data_wy2039wm _database_code_depnum_ccdc_archive 'CCDC 734040' _audit_update_record ; 2009-05-21 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H21 N O' _chemical_formula_weight 279.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 10.2965(7) _cell_length_b 10.6213(7) _cell_length_c 14.1700(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.4070(10) _cell_angle_gamma 90.00 _cell_volume 1542.77(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8630 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9020 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3730 _reflns_number_gt 3225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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^)+(0.0866P)^2^+0.4888P] 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 3730 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 C1 C 0.22433(13) 0.21414(13) 0.70630(9) 0.0351(3) Uani 1 1 d . . . H1A H 0.1772 0.2798 0.7333 0.042 Uiso 1 1 calc R . . C2 C 0.19489(15) 0.18231(15) 0.61117(10) 0.0433(3) Uani 1 1 d . . . H2A H 0.1272 0.2253 0.5740 0.052 Uiso 1 1 calc R . . C3 C 0.26447(16) 0.08806(14) 0.57095(9) 0.0414(3) Uani 1 1 d . . . H3A H 0.2444 0.0658 0.5063 0.050 Uiso 1 1 calc R . . C4 C 0.36348(15) 0.02647(13) 0.62557(9) 0.0389(3) Uani 1 1 d . . . H4A H 0.4125 -0.0370 0.5977 0.047 Uiso 1 1 calc R . . C5 C 0.39180(12) 0.05664(12) 0.72093(9) 0.0313(3) Uani 1 1 d . . . H5A H 0.4590 0.0128 0.7579 0.038 Uiso 1 1 calc R . . C6 C 0.32197(11) 0.15089(11) 0.76228(8) 0.0257(2) Uani 1 1 d . . . C7 C 0.35156(11) 0.18439(11) 0.86671(8) 0.0240(2) Uani 1 1 d . . . H7A H 0.3074 0.2659 0.8787 0.029 Uiso 1 1 calc R . . C8 C 0.56719(11) 0.28835(11) 0.85664(7) 0.0240(2) Uani 1 1 d . . . C9 C 0.51843(12) 0.40619(12) 0.82702(9) 0.0317(3) Uani 1 1 d . . . H9A H 0.4284 0.4246 0.8288 0.038 Uiso 1 1 calc R . . C10 C 0.60159(13) 0.49664(13) 0.79486(10) 0.0359(3) Uani 1 1 d . . . H10A H 0.5677 0.5768 0.7758 0.043 Uiso 1 1 calc R . . C11 C 0.73281(13) 0.47174(13) 0.79020(9) 0.0354(3) Uani 1 1 d . . . H11A H 0.7889 0.5343 0.7685 0.042 Uiso 1 1 calc R . . C12 C 0.78114(12) 0.35430(13) 0.81764(9) 0.0330(3) Uani 1 1 d . . . H12A H 0.8708 0.3358 0.8139 0.040 Uiso 1 1 calc R . . C13 C 0.69961(11) 0.26341(11) 0.85054(8) 0.0279(3) Uani 1 1 d . . . H13A H 0.7341 0.1833 0.8692 0.033 Uiso 1 1 calc R . . C14 C 0.30093(11) 0.08303(11) 0.93297(8) 0.0256(2) Uani 1 1 d . . . H14A H 0.3500 0.0032 0.9244 0.031 Uiso 1 1 calc R . . C15 C 0.32871(11) 0.12514(11) 1.03547(8) 0.0258(2) Uani 1 1 d . . . C16 C 0.24964(14) 0.23500(13) 1.06462(9) 0.0366(3) Uani 1 1 d . . . H16A H 0.2719 0.3112 1.0293 0.044 Uiso 1 1 calc R . . H16B H 0.2698 0.2516 1.1332 0.044 Uiso 1 1 calc R . . C17 C 0.10354(15) 0.20508(17) 1.04346(12) 0.0491(4) Uani 1 1 d . . . H17A H 0.0793 0.1370 1.0862 0.059 Uiso 1 1 calc R . . H17B H 0.0518 0.2807 1.0564 0.059 Uiso 1 1 calc R . . C18 C 0.07020(13) 0.16438(16) 0.94076(11) 0.0460(4) Uani 1 1 d . . . H18A H -0.0227 0.1393 0.9315 0.055 Uiso 1 1 calc R . . H18B H 0.0828 0.2365 0.8983 0.055 Uiso 1 1 calc R . . C19 C 0.15459(13) 0.05497(14) 0.91418(10) 0.0369(3) Uani 1 1 d . . . H19A H 0.1340 0.0354 0.8461 0.044 Uiso 1 1 calc R . . H19B H 0.1334 -0.0203 0.9510 0.044 Uiso 1 1 calc R . . N1 N 0.49074(9) 0.19785(9) 0.89666(7) 0.0258(2) Uani 1 1 d . . . H1B H 0.5272 0.1477 0.9410 0.031 Uiso 1 1 calc R . . O1 O 0.40316(9) 0.06796(9) 1.09180(6) 0.0369(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0371(7) 0.0364(7) 0.0308(6) 0.0050(5) -0.0023(5) 0.0044(5) C2 0.0493(8) 0.0467(8) 0.0313(6) 0.0093(6) -0.0107(6) 0.0010(6) C3 0.0587(9) 0.0410(7) 0.0231(6) 0.0033(5) -0.0031(5) -0.0082(6) C4 0.0519(8) 0.0367(7) 0.0288(6) -0.0014(5) 0.0065(5) -0.0008(6) C5 0.0322(6) 0.0343(6) 0.0272(6) 0.0031(4) 0.0013(4) 0.0006(5) C6 0.0254(5) 0.0283(5) 0.0232(5) 0.0039(4) 0.0007(4) -0.0044(4) C7 0.0219(5) 0.0258(5) 0.0241(5) 0.0020(4) 0.0013(4) -0.0012(4) C8 0.0243(5) 0.0278(5) 0.0195(5) -0.0012(4) 0.0008(4) -0.0029(4) C9 0.0250(5) 0.0318(6) 0.0381(6) 0.0057(5) 0.0019(5) 0.0000(5) C10 0.0343(7) 0.0324(6) 0.0405(7) 0.0094(5) 0.0002(5) -0.0031(5) C11 0.0340(6) 0.0404(7) 0.0326(6) 0.0049(5) 0.0073(5) -0.0098(5) C12 0.0259(6) 0.0418(7) 0.0322(6) -0.0033(5) 0.0083(5) -0.0027(5) C13 0.0274(6) 0.0294(6) 0.0271(5) -0.0025(4) 0.0036(4) 0.0012(4) C14 0.0257(5) 0.0255(5) 0.0258(5) 0.0029(4) 0.0026(4) -0.0015(4) C15 0.0240(5) 0.0278(5) 0.0258(5) 0.0045(4) 0.0043(4) -0.0010(4) C16 0.0469(8) 0.0334(6) 0.0303(6) 0.0014(5) 0.0079(5) 0.0090(5) C17 0.0397(8) 0.0584(9) 0.0522(9) 0.0119(7) 0.0200(7) 0.0190(7) C18 0.0227(6) 0.0621(10) 0.0533(9) 0.0212(7) 0.0040(6) 0.0020(6) C19 0.0295(6) 0.0448(7) 0.0355(6) 0.0088(5) -0.0009(5) -0.0127(5) N1 0.0225(5) 0.0287(5) 0.0254(4) 0.0055(4) -0.0011(4) -0.0022(4) O1 0.0364(5) 0.0458(5) 0.0281(4) 0.0076(4) 0.0016(4) 0.0100(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 C1 C6 1.3932(16) . ? C1 C2 1.3951(19) . ? C1 H1A 0.9500 . ? C2 C3 1.385(2) . ? C2 H2A 0.9500 . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3926(17) . ? C4 H4A 0.9500 . ? C5 C6 1.3935(17) . ? C5 H5A 0.9500 . ? C6 C7 1.5245(15) . ? C7 N1 1.4627(14) . ? C7 C14 1.5507(15) . ? C7 H7A 1.0000 . ? C8 N1 1.3962(14) . ? C8 C9 1.3982(17) . ? C8 C13 1.3996(16) . ? C9 C10 1.3919(17) . ? C9 H9A 0.9500 . ? C10 C11 1.3845(19) . ? C10 H10A 0.9500 . ? C11 C12 1.385(2) . ? C11 H11A 0.9500 . ? C12 C13 1.3884(17) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C15 1.5208(15) . ? C14 C19 1.5345(16) . ? C14 H14A 1.0000 . ? C15 O1 1.2159(14) . ? C15 C16 1.5028(17) . ? C16 C17 1.539(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.526(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? N1 H1B 0.8800 . ? 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 C6 C1 C2 120.84(13) . . ? C6 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? C3 C2 C1 119.95(13) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 119.59(12) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 120.62(13) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 120.28(12) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C1 C6 C5 118.70(11) . . ? C1 C6 C7 120.50(11) . . ? C5 C6 C7 120.80(10) . . ? N1 C7 C6 113.90(9) . . ? N1 C7 C14 105.56(9) . . ? C6 C7 C14 112.20(9) . . ? N1 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? C14 C7 H7A 108.3 . . ? N1 C8 C9 122.54(10) . . ? N1 C8 C13 118.98(10) . . ? C9 C8 C13 118.38(11) . . ? C10 C9 C8 120.10(11) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C11 C10 C9 121.13(12) . . ? C11 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? C10 C11 C12 119.02(11) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 120.5 . . ? C11 C12 C13 120.52(11) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C12 C13 C8 120.83(11) . . ? C12 C13 H13A 119.6 . . ? C8 C13 H13A 119.6 . . ? C15 C14 C19 108.43(10) . . ? C15 C14 C7 109.29(9) . . ? C19 C14 C7 114.23(9) . . ? C15 C14 H14A 108.2 . . ? C19 C14 H14A 108.2 . . ? C7 C14 H14A 108.2 . . ? O1 C15 C16 122.12(11) . . ? O1 C15 C14 122.03(11) . . ? C16 C15 C14 115.65(10) . . ? C15 C16 C17 109.33(12) . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? C18 C17 C16 111.85(11) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 111.75(12) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C18 C19 C14 112.55(11) . . ? C18 C19 H19A 109.1 . . ? C14 C19 H19A 109.1 . . ? C18 C19 H19B 109.1 . . ? C14 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C8 N1 C7 121.60(9) . . ? C8 N1 H1B 119.2 . . ? C7 N1 H1B 119.2 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.635 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.046 # Attachment '- SBiBF4-compound 3 (CCDC755139).cif' #============================================================================== data_wy2049wc _database_code_depnum_ccdc_archive 'CCDC 755139' #TrackingRef '- SBiBF4-compound 3 (CCDC755139).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2010-02-03 # Formatted by publCIF ; _chemical_name_common 2010-02-03 _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 B Bi F4 O S' _chemical_formula_sum 'C56 H56 B4 Bi4 F16 O4 S4' _chemical_formula_weight 2104.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8004(8) _cell_length_b 11.5529(6) _cell_length_c 9.8253(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.0050(10) _cell_angle_gamma 90.00 _cell_volume 1564.34(15) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9576 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 11.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6814 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; 2010-02-03 # Formatted by publCIF ; _diffrn_ambient_temperature 296(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9576 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3783 _reflns_number_gt 3681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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^)+(0.0493P)^2^+24.8946P] 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 3783 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.734577(17) -0.54208(2) 0.47908(2) 0.01850(10) Uani 1 1 d . . . S1 S 0.72188(14) -0.34750(16) 0.32714(19) 0.0258(4) Uani 1 1 d . . . O1 O 0.7438(5) -0.6681(5) 0.6858(6) 0.0329(13) Uani 1 1 d D . . H1A H 0.755(8) -0.671(11) 0.772(3) 0.049 Uiso 1 1 d D . . H1B H 0.758(8) -0.739(3) 0.679(13) 0.049 Uiso 1 1 d D . . C1 C 0.6226(5) -0.4389(6) 0.5864(7) 0.0203(13) Uani 1 1 d . . . C2 C 0.5652(5) -0.4922(7) 0.6784(8) 0.0254(14) Uani 1 1 d . . . H2 H 0.5766 -0.5692 0.7017 0.030 Uiso 1 1 calc R . . C3 C 0.4898(6) -0.4319(8) 0.7372(9) 0.0326(17) Uani 1 1 d . . . H3 H 0.4533 -0.4668 0.8026 0.039 Uiso 1 1 calc R . . C4 C 0.4711(6) -0.3196(8) 0.6959(9) 0.0349(19) Uani 1 1 d . . . H4 H 0.4193 -0.2799 0.7309 0.042 Uiso 1 1 calc R . . C5 C 0.5279(6) -0.2649(7) 0.6035(9) 0.0315(17) Uani 1 1 d . . . H5 H 0.5148 -0.1886 0.5787 0.038 Uiso 1 1 calc R . . C6 C 0.6051(5) -0.3238(6) 0.5467(7) 0.0225(14) Uani 1 1 d . . . C7 C 0.6710(6) -0.2580(6) 0.4574(8) 0.0275(15) Uani 1 1 d . . . H7A H 0.7235 -0.2245 0.5138 0.033 Uiso 1 1 calc R . . H7B H 0.6348 -0.1950 0.4137 0.033 Uiso 1 1 calc R . . C8 C 0.8499(6) -0.3119(8) 0.3511(9) 0.0329(17) Uani 1 1 d . . . H8A H 0.8844 -0.3490 0.2795 0.039 Uiso 1 1 calc R . . H8B H 0.8573 -0.2289 0.3406 0.039 Uiso 1 1 calc R . . C9 C 0.8967(5) -0.3470(7) 0.4865(8) 0.0252(14) Uani 1 1 d . . . C10 C 0.9788(6) -0.2861(8) 0.5363(9) 0.0319(17) Uani 1 1 d . . . H10 H 0.9987 -0.2208 0.4899 0.038 Uiso 1 1 calc R . . C11 C 1.0302(5) -0.3207(7) 0.6516(9) 0.0302(17) Uani 1 1 d . . . H11 H 1.0848 -0.2793 0.6825 0.036 Uiso 1 1 calc R . . C12 C 1.0015(6) -0.4169(8) 0.7226(8) 0.0292(16) Uani 1 1 d . . . H12 H 1.0370 -0.4407 0.8007 0.035 Uiso 1 1 calc R . . C13 C 0.9189(6) -0.4783(7) 0.6769(8) 0.0245(14) Uani 1 1 d . . . H13 H 0.8990 -0.5429 0.7245 0.029 Uiso 1 1 calc R . . C14 C 0.8664(5) -0.4418(6) 0.5588(7) 0.0203(13) Uani 1 1 d . . . F1 F 0.7576(5) -0.9027(5) 0.6653(5) 0.0458(14) Uani 1 1 d . . . F2 F 0.8211(5) -1.0391(6) 0.5323(9) 0.063(2) Uani 1 1 d . . . F3 F 0.7966(8) -0.8558(6) 0.4563(8) 0.085(3) Uani 1 1 d . . . F4 F 0.6684(6) -0.9748(7) 0.4878(11) 0.088(3) Uani 1 1 d . . . B1 B 0.7611(8) -0.9441(8) 0.5319(9) 0.032(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02168(15) 0.01643(14) 0.01706(14) -0.00333(8) -0.00215(9) 0.00145(9) S1 0.0298(9) 0.0251(8) 0.0217(8) 0.0019(7) -0.0044(7) -0.0008(7) O1 0.047(3) 0.023(3) 0.028(3) 0.002(2) -0.001(3) 0.005(2) C1 0.019(3) 0.020(3) 0.022(3) -0.002(3) -0.003(2) 0.001(2) C2 0.020(3) 0.027(4) 0.029(4) -0.004(3) 0.000(3) -0.003(3) C3 0.027(4) 0.036(4) 0.035(4) -0.010(4) 0.003(3) -0.005(3) C4 0.021(3) 0.040(5) 0.043(5) -0.020(4) -0.003(3) 0.003(3) C5 0.026(4) 0.023(4) 0.045(5) -0.013(3) -0.006(3) 0.003(3) C6 0.021(3) 0.021(3) 0.025(3) -0.006(3) -0.008(3) 0.001(3) C7 0.031(4) 0.019(3) 0.032(4) 0.000(3) -0.006(3) 0.005(3) C8 0.034(4) 0.035(4) 0.029(4) 0.008(3) 0.001(3) -0.008(3) C9 0.023(3) 0.027(4) 0.026(4) -0.004(3) 0.000(3) 0.002(3) C10 0.026(4) 0.031(4) 0.039(4) -0.005(3) 0.006(3) -0.006(3) C11 0.015(3) 0.035(4) 0.040(4) -0.012(3) -0.004(3) -0.003(3) C12 0.022(3) 0.037(4) 0.028(4) -0.007(3) -0.008(3) 0.009(3) C13 0.026(3) 0.022(3) 0.025(4) -0.006(3) -0.001(3) 0.001(3) C14 0.017(3) 0.022(3) 0.022(3) -0.007(3) -0.001(2) 0.005(2) F1 0.075(4) 0.041(3) 0.023(2) -0.002(2) 0.009(2) -0.006(3) F2 0.056(4) 0.046(4) 0.088(6) -0.021(3) 0.001(4) 0.008(3) F3 0.163(9) 0.048(4) 0.048(4) 0.005(3) 0.044(5) -0.023(5) F4 0.072(5) 0.071(5) 0.116(7) -0.034(5) -0.054(5) 0.009(4) B1 0.050(6) 0.025(4) 0.021(4) -0.004(3) 0.003(4) -0.002(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 2.256(7) . ? Bi1 C14 2.262(7) . ? Bi1 O1 2.497(6) . ? Bi1 S1 2.6991(19) . ? S1 C7 1.815(8) . ? S1 C8 1.817(9) . ? O1 H1A 0.85(2) . ? O1 H1B 0.85(2) . ? C1 C2 1.379(10) . ? C1 C6 1.403(10) . ? C2 C3 1.401(11) . ? C2 H2 0.9300 . ? C3 C4 1.380(13) . ? C3 H3 0.9300 . ? C4 C5 1.383(13) . ? C4 H4 0.9300 . ? C5 C6 1.405(10) . ? C5 H5 0.9300 . ? C6 C7 1.502(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.505(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.382(11) . ? C9 C10 1.400(11) . ? C10 C11 1.364(12) . ? C10 H10 0.9300 . ? C11 C12 1.381(12) . ? C11 H11 0.9300 . ? C12 C13 1.396(11) . ? C12 H12 0.9300 . ? C13 C14 1.401(10) . ? C13 H13 0.9300 . ? F1 B1 1.399(10) . ? F2 B1 1.375(12) . ? F3 B1 1.368(11) . ? F4 B1 1.375(13) . ? 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 C14 97.2(2) . . ? C1 Bi1 O1 86.3(2) . . ? C14 Bi1 O1 90.6(2) . . ? C1 Bi1 S1 78.00(19) . . ? C14 Bi1 S1 78.03(19) . . ? O1 Bi1 S1 159.18(14) . . ? C7 S1 C8 100.9(4) . . ? C7 S1 Bi1 95.8(3) . . ? C8 S1 Bi1 94.7(3) . . ? Bi1 O1 H1A 146(9) . . ? Bi1 O1 H1B 120(9) . . ? H1A O1 H1B 90(10) . . ? C2 C1 C6 120.6(7) . . ? C2 C1 Bi1 120.1(5) . . ? C6 C1 Bi1 118.9(5) . . ? C1 C2 C3 120.8(8) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 118.6(8) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 121.2(8) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 120.5(8) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.1(7) . . ? C1 C6 C7 122.8(7) . . ? C5 C6 C7 118.8(7) . . ? C6 C7 S1 113.1(5) . . ? C6 C7 H7A 109.0 . . ? S1 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? S1 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 S1 115.1(6) . . ? C9 C8 H8A 108.5 . . ? S1 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? S1 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C14 C9 C10 118.7(7) . . ? C14 C9 C8 122.7(7) . . ? C10 C9 C8 118.4(7) . . ? C11 C10 C9 121.2(8) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.3(7) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 119.8(7) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 119.4(7) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 120.5(7) . . ? C9 C14 Bi1 119.2(5) . . ? C13 C14 Bi1 120.3(5) . . ? F3 B1 F2 111.4(9) . . ? F3 B1 F4 112.1(10) . . ? F2 B1 F4 110.1(8) . . ? F3 B1 F1 106.6(7) . . ? F2 B1 F1 108.7(8) . . ? F4 B1 F1 107.8(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B F1 0.85(2) 1.90(4) 2.725(8) 166(12) . O1 H1A F3 0.85(2) 1.90(4) 2.733(10) 166(12) 4_546 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 6.214 _refine_diff_density_min -1.495 _refine_diff_density_rms 0.199 #============================================================================== # Formatted by publCIF data_wy2211wc _database_code_depnum_ccdc_archive 'CCDC 791966' #TrackingRef '- S+Bi+C4-compound 4 (CCDC791966).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2010-08-07 # Formatted by publCIF ; _chemical_name_common 2010-08-07 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Bi F9 O4 S2' _chemical_formula_weight 738.39 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.5855(16) _cell_length_b 11.7682(10) _cell_length_c 9.9156(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.0340(10) _cell_angle_gamma 90.00 _cell_volume 2272.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13168 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.26 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 8.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3652 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; 2010-08-07 # Formatted by publCIF ; _diffrn_ambient_temperature 173(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13168 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.26 _reflns_number_total 5426 _reflns_number_gt 4941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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. DFIX Restraints have been used for the O-H distances in water molecules. ; _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^)+(0.0695P)^2^+0.7099P] 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 5426 _refine_ls_number_parameters 313 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.336309(7) -0.013216(14) 0.430476(14) 0.02653(8) Uani 1 1 d . . . C1 C 0.24214(19) 0.0830(3) 0.4763(3) 0.0254(7) Uani 1 1 d . . . C2 C 0.1987(2) 0.0380(4) 0.5646(4) 0.0298(8) Uani 1 1 d . . . H2A H 0.2102 -0.0317 0.6097 0.036 Uiso 1 1 calc R . . C3 C 0.1379(2) 0.0947(4) 0.5878(4) 0.0368(9) Uani 1 1 d . . . H3A H 0.1085 0.0635 0.6485 0.044 Uiso 1 1 calc R . . C4 C 0.1211(2) 0.1958(4) 0.5221(4) 0.0397(10) Uani 1 1 d . . . H4A H 0.0802 0.2346 0.5382 0.048 Uiso 1 1 calc R . . C5 C 0.1641(2) 0.2410(4) 0.4323(4) 0.0370(9) Uani 1 1 d . . . H5A H 0.1525 0.3111 0.3881 0.044 Uiso 1 1 calc R . . C6 C 0.2241(2) 0.1842(3) 0.4065(4) 0.0287(8) Uani 1 1 d . . . C7 C 0.2630(2) 0.2328(4) 0.2958(4) 0.0331(8) Uani 1 1 d . . . H7A H 0.2622 0.3167 0.3022 0.040 Uiso 1 1 calc R . . H7B H 0.2386 0.2114 0.2069 0.040 Uiso 1 1 calc R . . C8 C 0.3913(2) 0.2622(3) 0.4490(4) 0.0332(8) Uani 1 1 d . . . H8A H 0.4198 0.3250 0.4190 0.040 Uiso 1 1 calc R . . H8B H 0.3547 0.2962 0.4976 0.040 Uiso 1 1 calc R . . C9 C 0.4353(2) 0.1872(3) 0.5449(4) 0.0285(8) Uani 1 1 d . . . C10 C 0.4930(2) 0.2364(4) 0.6194(4) 0.0360(9) Uani 1 1 d . . . H10A H 0.5059 0.3122 0.6006 0.043 Uiso 1 1 calc R . . C11 C 0.5313(2) 0.1747(4) 0.7204(5) 0.0413(11) Uani 1 1 d . . . H11A H 0.5697 0.2087 0.7717 0.050 Uiso 1 1 calc R . . C12 C 0.5133(2) 0.0642(4) 0.7460(5) 0.0383(10) Uani 1 1 d . . . H12A H 0.5393 0.0222 0.8153 0.046 Uiso 1 1 calc R . . C13 C 0.4576(3) 0.0139(3) 0.6714(5) 0.0331(9) Uani 1 1 d . . . H13A H 0.4461 -0.0627 0.6890 0.040 Uiso 1 1 calc R . . C14 C 0.41775(18) 0.0753(3) 0.5698(4) 0.0251(7) Uani 1 1 d . . . C15 C 0.1933(2) 0.8929(4) -0.0114(4) 0.0350(9) Uani 1 1 d . . . C16 C 0.1563(2) 0.9077(4) 0.1173(5) 0.0388(10) Uani 1 1 d . . . C17 C 0.0899(2) 0.8371(5) 0.1195(5) 0.0459(11) Uani 1 1 d . . . C18 C 0.0433(3) 0.8766(7) 0.2260(6) 0.0659(17) Uani 1 1 d . . . F1 F 0.19312(15) 0.7823(3) -0.0452(3) 0.0559(8) Uani 1 1 d . . . F2 F 0.15689(16) 0.9501(4) -0.1126(3) 0.0622(9) Uani 1 1 d . . . F3 F 0.19884(14) 0.8769(3) 0.2253(3) 0.0587(9) Uani 1 1 d . . . F4 F 0.1408(2) 1.0171(3) 0.1324(5) 0.0679(12) Uani 1 1 d . . . F5 F 0.10621(17) 0.7281(3) 0.1462(4) 0.0643(9) Uani 1 1 d . . . F6 F 0.05304(15) 0.8412(4) -0.0030(3) 0.0676(10) Uani 1 1 d . . . F7 F 0.07714(18) 0.8877(4) 0.3458(3) 0.0730(10) Uani 1 1 d . . . F8 F 0.0114(3) 0.9719(5) 0.1911(7) 0.112(2) Uani 1 1 d . . . F9 F -0.00576(18) 0.7979(5) 0.2357(4) 0.0924(14) Uani 1 1 d . . . O1 O 0.32422(19) -0.1339(3) 0.6290(3) 0.0425(7) Uani 1 1 d D . . H1 H 0.318(2) -0.109(5) 0.707(3) 0.043 Uiso 1 1 d D . . H1A H 0.319(6) -0.206(2) 0.633(12) 0.182 Uiso 1 1 d D . . O2 O 0.2812(2) 1.0495(3) 0.0757(5) 0.0606(11) Uani 1 1 d . . . O3 O 0.2965(3) 0.9615(5) -0.1345(4) 0.0682(13) Uani 1 1 d . . . O4 O 0.32087(19) 0.8576(3) 0.0801(5) 0.0646(11) Uani 1 1 d . . . S1 S 0.35210(5) 0.18647(9) 0.30053(9) 0.0317(2) Uani 1 1 d . . . S2 S 0.28304(6) 0.94376(9) 0.00408(10) 0.0337(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02598(12) 0.02731(11) 0.02642(11) -0.00812(4) 0.00331(7) 0.00091(4) C1 0.0225(18) 0.0298(18) 0.0233(16) -0.0030(14) -0.0002(13) -0.0024(14) C2 0.024(2) 0.034(2) 0.031(2) -0.0006(16) 0.0029(15) -0.0037(16) C3 0.025(2) 0.052(3) 0.034(2) 0.0003(19) 0.0092(16) -0.0024(19) C4 0.027(2) 0.050(3) 0.042(2) -0.0024(19) 0.0048(17) 0.0109(18) C5 0.035(2) 0.039(2) 0.037(2) 0.0045(18) 0.0026(17) 0.0098(18) C6 0.026(2) 0.035(2) 0.0246(17) -0.0007(14) 0.0010(14) 0.0010(15) C7 0.030(2) 0.042(2) 0.0278(17) 0.0073(16) 0.0027(15) 0.0011(17) C8 0.037(2) 0.0281(19) 0.0352(19) -0.0005(16) 0.0052(16) -0.0046(16) C9 0.0250(19) 0.032(2) 0.0300(18) -0.0059(15) 0.0077(14) 0.0029(15) C10 0.026(2) 0.033(2) 0.049(2) -0.0086(18) 0.0064(17) -0.0015(16) C11 0.0175(19) 0.050(3) 0.054(3) -0.020(2) -0.0049(17) 0.0038(17) C12 0.023(2) 0.050(3) 0.041(2) -0.006(2) -0.0023(16) 0.0098(18) C13 0.029(2) 0.035(2) 0.035(2) -0.0010(15) 0.0034(18) 0.0079(15) C14 0.0171(17) 0.0307(19) 0.0279(17) -0.0064(14) 0.0043(13) 0.0036(13) C15 0.031(2) 0.040(2) 0.033(2) -0.0018(17) -0.0038(16) -0.0004(17) C16 0.038(2) 0.042(3) 0.035(2) 0.0008(19) -0.0006(17) -0.0022(19) C17 0.033(2) 0.061(3) 0.042(2) 0.006(2) -0.0054(19) -0.007(2) C18 0.043(3) 0.097(5) 0.059(3) 0.010(3) 0.009(3) -0.003(3) F1 0.0501(18) 0.0493(18) 0.0679(19) -0.0291(15) 0.0048(14) -0.0133(14) F2 0.0462(19) 0.099(3) 0.0391(16) 0.0251(17) -0.0077(13) 0.0007(18) F3 0.0446(17) 0.095(3) 0.0335(13) 0.0105(15) -0.0081(12) -0.0221(16) F4 0.075(3) 0.043(2) 0.091(3) -0.0091(17) 0.034(2) 0.0003(16) F5 0.063(2) 0.051(2) 0.080(2) 0.0045(17) 0.0111(17) -0.0167(16) F6 0.0404(17) 0.111(3) 0.0485(16) 0.0046(17) -0.0111(13) -0.0150(17) F7 0.065(2) 0.105(3) 0.0503(17) -0.0107(19) 0.0127(16) -0.011(2) F8 0.099(4) 0.121(4) 0.124(5) 0.032(4) 0.048(4) 0.052(3) F9 0.047(2) 0.153(4) 0.078(3) -0.001(3) 0.0141(19) -0.038(2) O1 0.059(2) 0.0264(15) 0.0432(16) 0.0003(13) 0.0123(15) -0.0026(14) O2 0.058(2) 0.0383(19) 0.087(3) -0.016(2) 0.018(2) -0.0171(18) O3 0.068(3) 0.103(4) 0.036(2) -0.011(2) 0.0124(19) -0.016(3) O4 0.0379(19) 0.043(2) 0.108(3) 0.029(2) -0.015(2) -0.0058(16) S1 0.0303(5) 0.0414(6) 0.0245(4) 0.0036(4) 0.0081(4) 0.0005(4) S2 0.0362(6) 0.0325(5) 0.0316(5) 0.0003(4) 0.0008(4) -0.0036(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 2.251(4) . ? Bi1 C14 2.252(4) . ? Bi1 O1 2.459(3) . ? Bi1 S1 2.7132(11) . ? C1 C2 1.389(5) . ? C1 C6 1.403(5) . ? C2 C3 1.405(6) . ? C2 H2A 0.9500 . ? C3 C4 1.379(7) . ? C3 H3A 0.9500 . ? C4 C5 1.394(6) . ? C4 H4A 0.9500 . ? C5 C6 1.399(6) . ? C5 H5A 0.9500 . ? C6 C7 1.513(5) . ? C7 S1 1.824(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.501(5) . ? C8 S1 1.820(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.389(6) . ? C9 C10 1.409(6) . ? C10 C11 1.391(6) . ? C10 H10A 0.9500 . ? C11 C12 1.378(7) . ? C11 H11A 0.9500 . ? C12 C13 1.386(7) . ? C12 H12A 0.9500 . ? C13 C14 1.407(6) . ? C13 H13A 0.9500 . ? C15 F1 1.345(5) . ? C15 F2 1.348(5) . ? C15 C16 1.543(6) . ? C15 S2 1.848(4) . ? C16 F4 1.334(6) . ? C16 F3 1.337(5) . ? C16 C17 1.545(7) . ? C17 F5 1.342(6) . ? C17 F6 1.347(5) . ? C17 C18 1.538(8) . ? C18 F7 1.305(7) . ? C18 F8 1.311(9) . ? C18 F9 1.346(8) . ? O1 H1 0.845(19) . ? O1 H1A 0.86(2) . ? O2 S2 1.435(4) . ? O3 S2 1.441(4) . ? O4 S2 1.424(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 C14 100.73(13) . . ? C1 Bi1 O1 88.82(13) . . ? C14 Bi1 O1 84.14(13) . . ? C1 Bi1 S1 78.27(10) . . ? C14 Bi1 S1 77.41(10) . . ? O1 Bi1 S1 154.94(8) . . ? C2 C1 C6 119.7(4) . . ? C2 C1 Bi1 120.3(3) . . ? C6 C1 Bi1 119.8(3) . . ? C1 C2 C3 120.5(4) . . ? C1 C2 H2A 119.7 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C5 C6 120.6(4) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C1 119.3(4) . . ? C5 C6 C7 116.7(4) . . ? C1 C6 C7 123.9(4) . . ? C6 C7 S1 114.9(3) . . ? C6 C7 H7A 108.5 . . ? S1 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? S1 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C9 C8 S1 112.9(3) . . ? C9 C8 H8A 109.0 . . ? S1 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? S1 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 119.8(4) . . ? C14 C9 C8 122.3(3) . . ? C10 C9 C8 117.7(4) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.5(4) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C12 C13 C14 120.6(4) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C9 C14 C13 119.0(4) . . ? C9 C14 Bi1 120.1(3) . . ? C13 C14 Bi1 120.3(3) . . ? F1 C15 F2 108.1(4) . . ? F1 C15 C16 109.0(4) . . ? F2 C15 C16 107.6(4) . . ? F1 C15 S2 108.2(3) . . ? F2 C15 S2 108.9(3) . . ? C16 C15 S2 114.9(3) . . ? F4 C16 F3 107.6(4) . . ? F4 C16 C15 109.5(4) . . ? F3 C16 C15 108.9(4) . . ? F4 C16 C17 108.4(4) . . ? F3 C16 C17 107.3(4) . . ? C15 C16 C17 114.9(4) . . ? F5 C17 F6 107.8(5) . . ? F5 C17 C18 107.5(5) . . ? F6 C17 C18 108.0(4) . . ? F5 C17 C16 109.5(4) . . ? F6 C17 C16 109.8(4) . . ? C18 C17 C16 114.1(5) . . ? F7 C18 F8 109.7(7) . . ? F7 C18 F9 107.6(5) . . ? F8 C18 F9 106.5(6) . . ? F7 C18 C17 112.0(5) . . ? F8 C18 C17 112.2(5) . . ? F9 C18 C17 108.7(6) . . ? Bi1 O1 H1 124(4) . . ? Bi1 O1 H1A 129(8) . . ? H1 O1 H1A 106(8) . . ? C8 S1 C7 101.29(19) . . ? C8 S1 Bi1 95.72(13) . . ? C7 S1 Bi1 96.58(14) . . ? O4 S2 O2 113.2(3) . . ? O4 S2 O3 118.1(3) . . ? O2 S2 O3 111.3(3) . . ? O4 S2 C15 104.5(2) . . ? O2 S2 C15 104.4(2) . . ? O3 S2 C15 103.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O4 0.86(2) 1.86(5) 2.676(5) 159(11) 4_566 O1 H1 O3 0.845(19) 1.87(2) 2.706(6) 172(5) 1_546 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 2.826 _refine_diff_density_min -2.214 _refine_diff_density_rms 0.186 # Attachment '- S+Bi+C8-compound 5 (CCDC733233).cif' #============================================================================== data_cd29204 _database_code_depnum_ccdc_archive 'CCDC 820463' #TrackingRef '- S+Bi+C8-compound 5 (CCDC733233).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H14 Bi F17 O4 S2' _chemical_formula_weight 938.43 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.7673(17) _cell_length_b 11.7803(8) _cell_length_c 10.0588(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.8420(10) _cell_angle_gamma 90.00 _cell_volume 2907.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4671 _cell_measurement_theta_min 4.794 _cell_measurement_theta_max 45.616 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.281 _exptl_crystal_size_mid 0.167 _exptl_crystal_size_min 0.155 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 6.347 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75125 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14436 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5096 _reflns_number_gt 3756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. DFIX restraints have used for the O-H distances in water molecules. MPLA restraints have used for the two phenyl-rings. Disorder was found for C8F17SO3. The O3 was found to be disordered over two occupied sites (occupancy of 0.54(4) and 0.46(4)).Each F atom was found to be disordered over two equally occupied sites. The DFIX and SIMU restraints have used. The occupancies of each group of four partially-occupied F atoms were refined competitively using a free variable. The final group occupancies are 0.633(7) and 0.367(7). ; _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^)+(0.0794P)^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 0.00055(18) _refine_ls_number_reflns 5096 _refine_ls_number_parameters 585 _refine_ls_number_restraints 306 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.991 _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 Bi Bi 0.628612(14) 1.02125(3) 1.07404(3) 0.06004(17) Uani 1 1 d . . . S1 S 0.61563(11) 0.8273(3) 1.2103(2) 0.0779(7) Uani 1 1 d . . . S2 S 0.66756(12) 0.0694(3) 0.5134(3) 0.0804(7) Uani 1 1 d DU . . O1 O 0.6391(4) 1.1365(7) 0.8768(8) 0.091(2) Uani 1 1 d D . . H1B H 0.640(5) 1.131(11) 0.793(2) 0.109 Uiso 1 1 d D . . H1A H 0.671(2) 1.164(10) 0.882(13) 0.109 Uiso 1 1 d D . . O2 O 0.6633(5) -0.0358(10) 0.4542(18) 0.186(5) Uani 1 1 d U A . O3 O 0.6499(8) 0.133(2) 0.619(2) 0.114(6) Uani 0.45(2) 1 d PU A 1 O4 O 0.6448(4) 0.1312(10) 0.4075(12) 0.158(4) Uani 1 1 d U A . O3' O 0.6532(8) 0.0309(17) 0.6430(16) 0.110(5) Uani 0.55(2) 1 d PU A 2 C1 C 0.5656(3) 0.9267(8) 0.9349(8) 0.056(2) Uani 1 1 d . . . C2 C 0.5337(4) 0.9835(8) 0.8312(11) 0.068(2) Uani 1 1 d . . . H2 H 0.5417 1.0586 0.8128 0.082 Uiso 1 1 calc R . . C3 C 0.4902(4) 0.9299(12) 0.7545(12) 0.087(3) Uani 1 1 d . . . H3 H 0.4702 0.9682 0.6832 0.104 Uiso 1 1 calc R . . C4 C 0.4768(4) 0.8233(11) 0.7828(12) 0.084(3) Uani 1 1 d . . . H4 H 0.4468 0.7883 0.7338 0.101 Uiso 1 1 calc R . . C5 C 0.5071(4) 0.7678(9) 0.8824(12) 0.083(3) Uani 1 1 d . . . H5 H 0.4981 0.6932 0.9001 0.100 Uiso 1 1 calc R . . C6 C 0.5524(3) 0.8182(8) 0.9622(9) 0.063(2) Uani 1 1 d . . . C7 C 0.5879(4) 0.7456(8) 1.0645(10) 0.076(3) Uani 1 1 d . . . H7A H 0.6176 0.7134 1.0230 0.092 Uiso 1 1 calc R . . H7B H 0.5664 0.6834 1.0924 0.092 Uiso 1 1 calc R . . C8 C 0.6850(4) 0.7812(10) 1.2278(10) 0.085(3) Uani 1 1 d . . . H8A H 0.7027 0.8043 1.3157 0.102 Uiso 1 1 calc R . . H8B H 0.6854 0.6989 1.2253 0.102 Uiso 1 1 calc R . . C9 C 0.7194(4) 0.8258(9) 1.1214(9) 0.069(2) Uani 1 1 d . . . C10 C 0.7657(4) 0.7727(10) 1.1089(12) 0.087(3) Uani 1 1 d . . . H10 H 0.7759 0.7093 1.1615 0.104 Uiso 1 1 calc R . . C11 C 0.7986(4) 0.8108(11) 1.0182(12) 0.090(3) Uani 1 1 d . . . H11 H 0.8300 0.7705 1.0075 0.108 Uiso 1 1 calc R . . C12 C 0.7863(4) 0.9055(12) 0.9448(12) 0.087(3) Uani 1 1 d . . . H12 H 0.8097 0.9326 0.8870 0.104 Uiso 1 1 calc R . . C13 C 0.7380(4) 0.9617(8) 0.9573(10) 0.066(2) Uani 1 1 d . . . H13 H 0.7286 1.0262 0.9060 0.079 Uiso 1 1 calc R . . C14 C 0.7038(3) 0.9234(8) 1.0447(8) 0.060(2) Uani 1 1 d . . . C15 C 0.7382(6) 0.1072(12) 0.5388(11) 0.113(4) Uani 1 1 d D A . C16 C 0.7715(4) 0.0909(9) 0.4246(10) 0.086(3) Uani 1 1 d D . . C17 C 0.8302(5) 0.1243(12) 0.4417(13) 0.114(4) Uani 1 1 d D A . C18 C 0.8657(5) 0.1012(11) 0.3380(13) 0.107(4) Uani 1 1 d D . . C19 C 0.9218(6) 0.1472(17) 0.3490(17) 0.164(8) Uani 1 1 d D A . C20 C 0.9584(8) 0.1060(17) 0.2550(18) 0.176(5) Uani 1 1 d DU . . C21 C 1.0151(8) 0.152(2) 0.270(2) 0.196(4) Uani 1 1 d DU A . C22 C 1.0544(8) 0.127(2) 0.183(2) 0.205(5) Uani 1 1 d DU . . F1 F 0.7424(12) 0.2175(16) 0.583(3) 0.174(9) Uani 0.641(7) 1 d PDU A 1 F2 F 0.7634(11) 0.065(2) 0.6541(13) 0.160(8) Uani 0.641(7) 1 d PDU A 1 F3 F 0.7417(7) 0.1240(19) 0.3076(13) 0.138(6) Uani 0.641(7) 1 d PDU A 1 F4 F 0.7728(8) -0.0234(11) 0.405(2) 0.131(6) Uani 0.641(7) 1 d PDU A 1 F5 F 0.8268(8) 0.2437(12) 0.422(2) 0.170(6) Uani 0.641(7) 1 d PDU A 1 F6 F 0.8549(7) 0.115(2) 0.5638(13) 0.148(6) Uani 0.641(7) 1 d PDU A 1 F7 F 0.8375(7) 0.1147(18) 0.2160(14) 0.138(5) Uani 0.641(7) 1 d PDU A 1 F8 F 0.8731(8) -0.0173(10) 0.352(2) 0.158(6) Uani 0.641(7) 1 d PDU A 1 F9 F 0.9051(11) 0.2521(16) 0.294(3) 0.237(9) Uani 0.641(7) 1 d PDU A 1 F10 F 0.9448(10) 0.157(2) 0.4738(17) 0.162(8) Uani 0.641(7) 1 d PDU A 1 F11 F 0.9362(11) 0.130(2) 0.1267(17) 0.177(7) Uani 0.641(7) 1 d PDU A 1 F12 F 0.9659(12) -0.0061(16) 0.239(3) 0.198(7) Uani 0.641(7) 1 d PDU A 1 F13 F 1.0014(9) 0.2536(19) 0.201(3) 0.218(6) Uani 0.641(7) 1 d PDU A 1 F14 F 1.0425(8) 0.158(2) 0.3954(19) 0.191(6) Uani 0.641(7) 1 d PDU A 1 F15 F 1.0276(12) 0.144(3) 0.063(2) 0.227(8) Uani 0.641(7) 1 d PDU A 1 F16 F 1.1036(7) 0.157(2) 0.195(2) 0.201(6) Uani 0.641(7) 1 d PDU A 1 F17 F 1.0649(11) 0.0167(19) 0.184(3) 0.215(7) Uani 0.641(7) 1 d PDU A 1 F1' F 0.737(2) 0.2221(19) 0.531(6) 0.186(14) Uani 0.359(7) 1 d PDU A 2 F2' F 0.766(3) 0.022(4) 0.606(4) 0.188(13) Uani 0.359(7) 1 d PDU A 2 F3' F 0.7490(15) 0.184(2) 0.355(3) 0.148(10) Uani 0.359(7) 1 d PDU A 2 F4' F 0.7555(15) 0.010(3) 0.339(3) 0.128(8) Uani 0.359(7) 1 d PDU A 2 F5' F 0.8442(14) 0.207(3) 0.526(4) 0.153(8) Uani 0.359(7) 1 d PDU A 2 F6' F 0.8500(13) 0.033(3) 0.523(3) 0.145(9) Uani 0.359(7) 1 d PDU A 2 F7' F 0.8482(10) 0.210(2) 0.284(3) 0.186(7) Uani 0.359(7) 1 d PDU A 2 F8' F 0.8425(15) 0.043(3) 0.234(3) 0.144(7) Uani 0.359(7) 1 d PDU A 2 F9' F 0.9392(17) 0.2548(18) 0.333(5) 0.251(13) Uani 0.359(7) 1 d PDU A 2 F10' F 0.939(2) 0.090(4) 0.461(3) 0.190(12) Uani 0.359(7) 1 d PDU A 2 F11' F 0.934(2) 0.065(4) 0.138(3) 0.173(7) Uani 0.359(7) 1 d PDU A 2 F12' F 0.9759(19) 0.010(3) 0.332(5) 0.186(6) Uani 0.359(7) 1 d PDU A 2 F13' F 1.0228(16) 0.258(3) 0.321(4) 0.204(7) Uani 0.359(7) 1 d PDU A 2 F14' F 1.0345(16) 0.068(3) 0.362(4) 0.196(6) Uani 0.359(7) 1 d PDU A 2 F17' F 1.0468(19) 0.087(5) 0.061(3) 0.208(8) Uani 0.359(7) 1 d PDU A 2 F16' F 1.0922(14) 0.100(4) 0.283(4) 0.208(6) Uani 0.359(7) 1 d PDU A 2 F15' F 1.0658(15) 0.238(3) 0.169(4) 0.214(7) Uani 0.359(7) 1 d PDU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.0703(3) 0.0610(2) 0.0505(2) -0.01283(15) 0.01419(16) 0.00074(15) S1 0.0864(16) 0.0925(19) 0.0605(14) 0.0151(13) 0.0309(13) 0.0035(14) S2 0.1033(19) 0.0713(17) 0.0679(16) 0.0052(14) 0.0160(14) 0.0034(15) O1 0.124(6) 0.072(5) 0.076(5) 0.003(4) 0.017(5) -0.018(4) O2 0.156(9) 0.129(9) 0.292(14) -0.053(9) 0.093(10) -0.043(7) O3 0.128(11) 0.118(13) 0.098(10) -0.035(10) 0.019(9) 0.031(11) O4 0.123(7) 0.147(9) 0.190(10) 0.062(8) -0.027(7) -0.026(6) O3' 0.147(11) 0.119(11) 0.066(8) -0.012(8) 0.023(8) -0.011(9) C1 0.050(4) 0.065(5) 0.054(5) -0.011(4) 0.014(4) 0.003(4) C2 0.067(6) 0.066(6) 0.072(6) -0.010(5) 0.011(5) 0.002(4) C3 0.071(6) 0.104(9) 0.083(7) -0.019(7) 0.002(6) 0.023(6) C4 0.063(6) 0.083(8) 0.104(9) -0.029(7) -0.003(6) 0.006(5) C5 0.069(6) 0.065(7) 0.120(9) -0.030(6) 0.029(6) -0.007(5) C6 0.061(5) 0.065(6) 0.068(6) -0.015(5) 0.030(4) 0.001(4) C7 0.077(6) 0.072(7) 0.087(7) 0.008(5) 0.038(5) 0.000(5) C8 0.110(8) 0.077(7) 0.070(6) 0.019(5) 0.019(6) 0.010(6) C9 0.067(6) 0.084(7) 0.055(5) 0.005(5) 0.012(4) -0.006(5) C10 0.070(6) 0.090(8) 0.103(8) 0.016(6) 0.021(6) 0.020(6) C11 0.060(6) 0.111(10) 0.101(9) -0.001(7) 0.019(6) 0.019(6) C12 0.061(6) 0.113(10) 0.091(8) -0.014(7) 0.025(6) -0.001(6) C13 0.067(6) 0.069(6) 0.063(6) -0.001(5) 0.014(5) -0.009(4) C14 0.058(5) 0.073(6) 0.048(5) -0.004(4) 0.009(4) 0.000(4) C15 0.139(11) 0.133(13) 0.064(7) -0.004(8) 0.001(8) -0.004(10) C16 0.110(9) 0.071(8) 0.074(7) 0.009(6) 0.005(6) -0.012(6) C17 0.110(10) 0.125(13) 0.106(11) 0.008(10) 0.007(9) 0.016(9) C18 0.117(10) 0.109(12) 0.094(10) 0.006(8) 0.012(8) -0.006(8) C19 0.108(12) 0.24(3) 0.155(18) 0.060(18) 0.040(12) 0.025(14) C20 0.164(9) 0.185(10) 0.178(10) 0.031(9) 0.015(9) 0.000(9) C21 0.182(8) 0.205(10) 0.199(9) 0.030(8) 0.017(8) 0.002(9) C22 0.187(9) 0.226(11) 0.205(10) 0.026(10) 0.033(9) 0.017(9) F1 0.123(10) 0.191(13) 0.20(2) -0.142(12) -0.011(13) -0.029(9) F2 0.108(8) 0.33(3) 0.038(8) 0.048(12) -0.002(9) 0.018(13) F3 0.143(9) 0.209(16) 0.055(7) 0.014(9) -0.010(7) -0.040(12) F4 0.139(13) 0.117(11) 0.142(15) -0.034(9) 0.037(11) -0.027(8) F5 0.195(12) 0.094(9) 0.210(15) -0.024(10) -0.004(12) 0.004(9) F6 0.150(9) 0.198(18) 0.082(8) -0.034(10) -0.032(7) -0.002(13) F7 0.166(10) 0.145(13) 0.097(8) 0.002(9) -0.009(7) -0.024(11) F8 0.194(14) 0.092(9) 0.204(15) 0.007(9) 0.086(12) 0.001(8) F9 0.27(2) 0.111(11) 0.295(18) 0.038(12) -0.070(18) -0.016(13) F10 0.147(11) 0.23(2) 0.100(9) -0.050(12) -0.004(8) -0.072(14) F11 0.182(11) 0.209(16) 0.134(10) 0.016(11) -0.003(9) 0.004(14) F12 0.201(12) 0.183(12) 0.212(14) 0.008(12) 0.033(13) 0.006(10) F13 0.210(12) 0.208(13) 0.233(13) 0.039(12) 0.019(12) -0.002(12) F14 0.185(11) 0.200(13) 0.175(11) -0.013(11) -0.024(10) -0.014(11) F15 0.262(16) 0.255(18) 0.166(12) 0.025(13) 0.030(13) 0.022(14) F16 0.135(10) 0.250(14) 0.228(13) 0.021(12) 0.066(10) 0.006(10) F17 0.204(13) 0.233(15) 0.211(13) 0.007(12) 0.046(12) 0.053(11) F1' 0.153(17) 0.166(17) 0.23(4) -0.127(17) -0.03(2) -0.017(14) F2' 0.149(17) 0.34(3) 0.068(19) 0.07(2) -0.01(2) 0.03(2) F3' 0.150(15) 0.19(2) 0.101(17) 0.054(16) -0.011(15) -0.014(18) F4' 0.124(15) 0.166(16) 0.094(15) -0.041(13) 0.019(13) -0.037(14) F5' 0.168(14) 0.145(17) 0.136(15) -0.065(14) -0.013(13) -0.025(14) F6' 0.137(15) 0.19(2) 0.099(15) 0.027(15) -0.031(14) 0.021(18) F7' 0.213(14) 0.127(13) 0.207(15) 0.028(13) -0.015(14) -0.004(13) F8' 0.169(14) 0.141(17) 0.124(14) -0.041(14) 0.033(13) -0.027(15) F9' 0.30(3) 0.095(15) 0.32(3) 0.020(18) -0.11(3) -0.02(2) F10' 0.174(19) 0.27(3) 0.119(16) -0.02(2) -0.019(15) -0.05(2) F11' 0.176(13) 0.191(16) 0.148(13) 0.006(14) 0.011(12) -0.002(15) F12' 0.177(10) 0.189(11) 0.190(11) 0.029(10) 0.013(11) 0.003(10) F13' 0.198(14) 0.195(14) 0.214(15) 0.006(14) 0.007(13) -0.015(13) F14' 0.181(10) 0.204(11) 0.199(11) 0.028(10) 0.010(10) 0.004(10) F17' 0.215(15) 0.237(17) 0.177(14) 0.008(14) 0.045(13) 0.052(14) F16' 0.179(11) 0.236(13) 0.210(13) 0.023(12) 0.031(11) 0.015(11) F15' 0.184(13) 0.232(15) 0.232(14) 0.036(14) 0.047(13) -0.005(13) _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 Bi C14 2.243(8) . ? Bi C1 2.245(8) . ? Bi O1 2.447(7) . ? Bi S1 2.706(3) . ? S1 C8 1.788(11) . ? S1 C7 1.809(10) . ? S2 O4 1.349(10) . ? S2 O2 1.373(12) . ? S2 O3 1.413(17) . ? S2 O3' 1.469(17) . ? S2 C15 1.789(14) . ? O1 H1B 0.851(11) . ? O1 H1A 0.852(11) . ? C1 C6 1.356(12) . ? C1 C2 1.391(13) . ? C2 C3 1.389(15) . ? C2 H2 0.9300 . ? C3 C4 1.339(16) . ? C3 H3 0.9300 . ? C4 C5 1.338(15) . ? C4 H4 0.9300 . ? C5 C6 1.417(13) . ? C5 H5 0.9300 . ? C6 C7 1.522(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.547(13) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.327(13) . ? C9 C14 1.409(13) . ? C10 C11 1.379(15) . ? C10 H10 0.9300 . ? C11 C12 1.350(16) . ? C11 H11 0.9300 . ? C12 C13 1.388(14) . ? C12 H12 0.9300 . ? C13 C14 1.377(12) . ? C13 H13 0.9300 . ? C15 F2 1.334(16) . ? C15 F2' 1.35(2) . ? C15 F1' 1.36(2) . ? C15 F1 1.372(18) . ? C15 C16 1.515(13) . ? C16 F4' 1.311(19) . ? C16 F3 1.358(15) . ? C16 F4 1.361(15) . ? C16 F3' 1.379(19) . ? C16 C17 1.493(13) . ? C17 F6 1.299(15) . ? C17 F5' 1.311(18) . ? C17 F6' 1.394(18) . ? C17 F5 1.421(15) . ? C17 C18 1.479(14) . ? C18 F8' 1.314(19) . ? C18 F7 1.337(14) . ? C18 F8 1.413(15) . ? C18 F7' 1.432(17) . ? C18 C19 1.480(15) . ? C19 F10 1.311(17) . ? C19 F10' 1.33(2) . ? C19 F9' 1.36(2) . ? C19 F9 1.394(18) . ? C19 C20 1.478(17) . ? C20 F11' 1.33(2) . ? C20 F12 1.346(18) . ? C20 F11 1.362(18) . ? C20 F12' 1.40(2) . ? C20 C21 1.495(17) . ? C21 F13' 1.35(2) . ? C21 F14 1.349(18) . ? C21 F14' 1.39(2) . ? C21 F13 1.400(18) . ? C21 C22 1.430(18) . ? C22 F16 1.262(18) . ? C22 F17' 1.30(2) . ? C22 F15 1.308(19) . ? C22 F16' 1.32(2) . ? C22 F17 1.322(18) . ? C22 F15' 1.36(2) . ? F12' F14' 1.59(6) . ? F14' F16' 1.77(6) . ? 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 C14 Bi C1 100.5(3) . . ? C14 Bi O1 89.8(3) . . ? C1 Bi O1 84.9(3) . . ? C14 Bi S1 77.9(2) . . ? C1 Bi S1 77.1(2) . . ? O1 Bi S1 155.81(19) . . ? C8 S1 C7 99.9(5) . . ? C8 S1 Bi 97.3(3) . . ? C7 S1 Bi 95.6(3) . . ? O4 S2 O2 98.4(10) . . ? O4 S2 O3 99.8(11) . . ? O2 S2 O3 142.0(13) . . ? O4 S2 O3' 138.0(10) . . ? O2 S2 O3' 95.3(10) . . ? O3 S2 O3' 50.1(10) . . ? O4 S2 C15 105.8(6) . . ? O2 S2 C15 107.6(7) . . ? O3 S2 C15 99.2(10) . . ? O3' S2 C15 107.5(9) . . ? Bi O1 H1B 141(9) . . ? Bi O1 H1A 111(9) . . ? H1B O1 H1A 87(10) . . ? C6 C1 C2 118.5(8) . . ? C6 C1 Bi 120.5(7) . . ? C2 C1 Bi 120.3(7) . . ? C3 C2 C1 121.1(10) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 120.2(11) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.2(10) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 122.6(11) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C1 C6 C5 118.3(9) . . ? C1 C6 C7 122.3(8) . . ? C5 C6 C7 119.1(9) . . ? C6 C7 S1 111.7(7) . . ? C6 C7 H7A 109.3 . . ? S1 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? S1 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 S1 116.2(7) . . ? C9 C8 H8A 108.2 . . ? S1 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? S1 C8 H8B 108.2 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C14 120.6(9) . . ? C10 C9 C8 118.0(9) . . ? C14 C9 C8 121.3(8) . . ? C9 C10 C11 120.4(11) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 121.4(10) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 118.5(10) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 121.0(10) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 118.1(8) . . ? C13 C14 Bi 120.6(7) . . ? C9 C14 Bi 121.2(6) . . ? F2 C15 F2' 31(2) . . ? F2 C15 F1' 115(3) . . ? F2' C15 F1' 141(4) . . ? F2 C15 F1 93.7(18) . . ? F2' C15 F1 122(3) . . ? F1' C15 F1 22(4) . . ? F2 C15 C16 112.0(14) . . ? F2' C15 C16 89(2) . . ? F1' C15 C16 95(3) . . ? F1 C15 C16 109.7(17) . . ? F2 C15 S2 111.4(16) . . ? F2' C15 S2 108(3) . . ? F1' C15 S2 103(3) . . ? F1 C15 S2 108.2(16) . . ? C16 C15 S2 118.9(8) . . ? F4' C16 F3 63.8(19) . . ? F4' C16 F4 36.7(17) . . ? F3 C16 F4 100.4(14) . . ? F4' C16 F3' 100(2) . . ? F3 C16 F3' 36.5(13) . . ? F4 C16 F3' 136.9(19) . . ? F4' C16 C17 118.0(19) . . ? F3 C16 C17 115.4(12) . . ? F4 C16 C17 103.6(12) . . ? F3' C16 C17 99.8(17) . . ? F4' C16 C15 116.4(19) . . ? F3 C16 C15 109.5(12) . . ? F4 C16 C15 104.9(12) . . ? F3' C16 C15 93.5(18) . . ? C17 C16 C15 120.1(10) . . ? F6 C17 F5' 53.0(18) . . ? F6 C17 F6' 45.9(14) . . ? F5' C17 F6' 99(2) . . ? F6 C17 F5 102.8(17) . . ? F5' C17 F5 49.9(19) . . ? F6' C17 F5 148(2) . . ? F6 C17 C18 113.7(13) . . ? F5' C17 C18 117.7(18) . . ? F6' C17 C18 94.2(18) . . ? F5 C17 C18 96.6(12) . . ? F6 C17 C16 114.4(13) . . ? F5' C17 C16 115.9(18) . . ? F6' C17 C16 97.1(16) . . ? F5 C17 C16 101.9(12) . . ? C18 C17 C16 122.3(11) . . ? F8' C18 F7 38.3(16) . . ? F8' C18 F8 66.5(19) . . ? F7 C18 F8 104.8(15) . . ? F8' C18 F7' 95(2) . . ? F7 C18 F7' 56.7(16) . . ? F8 C18 F7' 161(2) . . ? F8' C18 C19 124(2) . . ? F7 C18 C19 113.1(13) . . ? F8 C18 C19 104.3(13) . . ? F7' C18 C19 86.3(12) . . ? F8' C18 C17 115(2) . . ? F7 C18 C17 109.8(13) . . ? F8 C18 C17 101.0(12) . . ? F7' C18 C17 85.8(12) . . ? C19 C18 C17 121.5(12) . . ? F10 C19 F10' 36(2) . . ? F10 C19 F9' 86(3) . . ? F10' C19 F9' 120(3) . . ? F10 C19 F9 112(2) . . ? F10' C19 F9 146(3) . . ? F9' C19 F9 37(2) . . ? F10 C19 C20 114.6(17) . . ? F10' C19 C20 103(3) . . ? F9' C19 C20 90.0(15) . . ? F9 C19 C20 102(2) . . ? F10 C19 C18 112.6(15) . . ? F10' C19 C18 94(2) . . ? F9' C19 C18 130(2) . . ? F9 C19 C18 94.1(14) . . ? C20 C19 C18 118.9(16) . . ? F11' C20 F12 66(2) . . ? F11' C20 F11 33(2) . . ? F12 C20 F11 98(2) . . ? F11' C20 F12' 106(3) . . ? F12 C20 F12' 41(2) . . ? F11 C20 F12' 138(3) . . ? F11' C20 C19 116(3) . . ? F12 C20 C19 120(2) . . ? F11 C20 C19 109.5(18) . . ? F12' C20 C19 95(3) . . ? F11' C20 C21 121(3) . . ? F12 C20 C21 103(2) . . ? F11 C20 C21 105.7(18) . . ? F12' C20 C21 91(2) . . ? C19 C20 C21 117.7(17) . . ? F13' C21 F14 65(2) . . ? F13' C21 F14' 113(3) . . ? F14 C21 F14' 48.0(18) . . ? F13' C21 F13 54(2) . . ? F14 C21 F13 119(2) . . ? F14' C21 F13 167(3) . . ? F13' C21 C22 111(2) . . ? F14 C21 C22 106.7(19) . . ? F14' C21 C22 93(3) . . ? F13 C21 C22 90.7(17) . . ? F13' C21 C20 117(3) . . ? F14 C21 C20 117.2(18) . . ? F14' C21 C20 92(2) . . ? F13 C21 C20 95.8(18) . . ? C22 C21 C20 125(2) . . ? F16 C22 F17' 102(3) . . ? F16 C22 F15 114(3) . . ? F17' C22 F15 37(2) . . ? F16 C22 F16' 54.2(19) . . ? F17' C22 F16' 129(3) . . ? F15 C22 F16' 164(3) . . ? F16 C22 F17 95(2) . . ? F17' C22 F17 70(3) . . ? F15 C22 F17 103(2) . . ? F16' C22 F17 69(3) . . ? F16 C22 F15' 61(2) . . ? F17' C22 F15' 105(4) . . ? F15 C22 F15' 81(3) . . ? F16' C22 F15' 100(3) . . ? F17 C22 F15' 155(3) . . ? F16 C22 C21 127(2) . . ? F17' C22 C21 129(3) . . ? F15 C22 C21 103(2) . . ? F16' C22 C21 93(3) . . ? F17 C22 C21 111(2) . . ? F15' C22 C21 91.4(15) . . ? C20 F12' F14' 88(2) . . ? C21 F14' F12' 88(2) . . ? C21 F14' F16' 77(2) . . ? F12' F14' F16' 141(4) . . ? C22 F16' F14' 82(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Bi S1 C8 18.4(4) . . . . ? C1 Bi S1 C8 122.3(4) . . . . ? O1 Bi S1 C8 79.4(7) . . . . ? C14 Bi S1 C7 -82.3(4) . . . . ? C1 Bi S1 C7 21.6(4) . . . . ? O1 Bi S1 C7 -21.4(6) . . . . ? C14 Bi C1 C6 67.6(7) . . . . ? O1 Bi C1 C6 156.4(7) . . . . ? S1 Bi C1 C6 -7.3(6) . . . . ? C14 Bi C1 C2 -122.2(7) . . . . ? O1 Bi C1 C2 -33.4(7) . . . . ? S1 Bi C1 C2 162.9(7) . . . . ? C6 C1 C2 C3 -1.6(13) . . . . ? Bi C1 C2 C3 -172.1(7) . . . . ? C1 C2 C3 C4 2.6(15) . . . . ? C2 C3 C4 C5 -2.5(16) . . . . ? C3 C4 C5 C6 1.5(16) . . . . ? C2 C1 C6 C5 0.6(12) . . . . ? Bi C1 C6 C5 171.0(6) . . . . ? C2 C1 C6 C7 174.0(8) . . . . ? Bi C1 C6 C7 -15.6(10) . . . . ? C4 C5 C6 C1 -0.6(14) . . . . ? C4 C5 C6 C7 -174.2(9) . . . . ? C1 C6 C7 S1 39.1(10) . . . . ? C5 C6 C7 S1 -147.6(7) . . . . ? C8 S1 C7 C6 -133.7(6) . . . . ? Bi S1 C7 C6 -35.3(6) . . . . ? C7 S1 C8 C9 72.1(9) . . . . ? Bi S1 C8 C9 -24.9(9) . . . . ? S1 C8 C9 C10 -163.0(9) . . . . ? S1 C8 C9 C14 20.3(13) . . . . ? C14 C9 C10 C11 -1.4(17) . . . . ? C8 C9 C10 C11 -178.1(11) . . . . ? C9 C10 C11 C12 3.2(19) . . . . ? C10 C11 C12 C13 -3.0(19) . . . . ? C11 C12 C13 C14 1.3(16) . . . . ? C12 C13 C14 C9 0.3(14) . . . . ? C12 C13 C14 Bi 175.9(8) . . . . ? C10 C9 C14 C13 -0.2(15) . . . . ? C8 C9 C14 C13 176.4(9) . . . . ? C10 C9 C14 Bi -175.9(8) . . . . ? C8 C9 C14 Bi 0.7(13) . . . . ? C1 Bi C14 C13 97.4(7) . . . . ? O1 Bi C14 C13 12.5(7) . . . . ? S1 Bi C14 C13 171.6(7) . . . . ? C1 Bi C14 C9 -87.1(8) . . . . ? O1 Bi C14 C9 -171.9(7) . . . . ? S1 Bi C14 C9 -12.9(7) . . . . ? O4 S2 C15 F2 169.9(15) . . . . ? O2 S2 C15 F2 -85.7(16) . . . . ? O3 S2 C15 F2 66.9(18) . . . . ? O3' S2 C15 F2 15.9(17) . . . . ? O4 S2 C15 F2' -157(2) . . . . ? O2 S2 C15 F2' -53(2) . . . . ? O3 S2 C15 F2' 100(2) . . . . ? O3' S2 C15 F2' 49(2) . . . . ? O4 S2 C15 F1' 46(3) . . . . ? O2 S2 C15 F1' 150(3) . . . . ? O3 S2 C15 F1' -57(3) . . . . ? O3' S2 C15 F1' -108(3) . . . . ? O4 S2 C15 F1 68.4(17) . . . . ? O2 S2 C15 F1 172.7(17) . . . . ? O3 S2 C15 F1 -34.7(19) . . . . ? O3' S2 C15 F1 -85.6(18) . . . . ? O4 S2 C15 C16 -57.6(12) . . . . ? O2 S2 C15 C16 46.8(13) . . . . ? O3 S2 C15 C16 -160.6(14) . . . . ? O3' S2 C15 C16 148.4(12) . . . . ? F2 C15 C16 F4' 104(3) . . . . ? F2' C15 C16 F4' 82(4) . . . . ? F1' C15 C16 F4' -136(3) . . . . ? F1 C15 C16 F4' -153(3) . . . . ? S2 C15 C16 F4' -28(3) . . . . ? F2 C15 C16 F3 173.7(19) . . . . ? F2' C15 C16 F3 152(3) . . . . ? F1' C15 C16 F3 -67(3) . . . . ? F1 C15 C16 F3 -83.8(19) . . . . ? S2 C15 C16 F3 41.5(16) . . . . ? F2 C15 C16 F4 67(2) . . . . ? F2' C15 C16 F4 45(3) . . . . ? F1' C15 C16 F4 -174(3) . . . . ? F1 C15 C16 F4 169.2(18) . . . . ? S2 C15 C16 F4 -65.6(14) . . . . ? F2 C15 C16 F3' -153(2) . . . . ? F2' C15 C16 F3' -174(3) . . . . ? F1' C15 C16 F3' -33(3) . . . . ? F1 C15 C16 F3' -50(2) . . . . ? S2 C15 C16 F3' 75.1(18) . . . . ? F2 C15 C16 C17 -49(2) . . . . ? F2' C15 C16 C17 -71(3) . . . . ? F1' C15 C16 C17 70(3) . . . . ? F1 C15 C16 C17 53.3(19) . . . . ? S2 C15 C16 C17 178.5(9) . . . . ? F4' C16 C17 F6 -122(3) . . . . ? F3 C16 C17 F6 165.2(19) . . . . ? F4 C16 C17 F6 -86.0(19) . . . . ? F3' C16 C17 F6 130(2) . . . . ? C15 C16 C17 F6 31(2) . . . . ? F4' C16 C17 F5' 179(3) . . . . ? F3 C16 C17 F5' 106(3) . . . . ? F4 C16 C17 F5' -145(3) . . . . ? F3' C16 C17 F5' 71(3) . . . . ? C15 C16 C17 F5' -29(3) . . . . ? F4' C16 C17 F6' -78(3) . . . . ? F3 C16 C17 F6' -150(2) . . . . ? F4 C16 C17 F6' -42(2) . . . . ? F3' C16 C17 F6' 175(2) . . . . ? C15 C16 C17 F6' 75(2) . . . . ? F4' C16 C17 F5 128(3) . . . . ? F3 C16 C17 F5 55.1(18) . . . . ? F4 C16 C17 F5 163.8(15) . . . . ? F3' C16 C17 F5 20(2) . . . . ? C15 C16 C17 F5 -79.6(15) . . . . ? F4' C16 C17 C18 22(3) . . . . ? F3 C16 C17 C18 -50.8(19) . . . . ? F4 C16 C17 C18 58.0(16) . . . . ? F3' C16 C17 C18 -86(2) . . . . ? C15 C16 C17 C18 174.6(11) . . . . ? F6 C17 C18 F8' 140(3) . . . . ? F5' C17 C18 F8' -161(3) . . . . ? F6' C17 C18 F8' 97(3) . . . . ? F5 C17 C18 F8' -113(2) . . . . ? C16 C17 C18 F8' -4(3) . . . . ? F6 C17 C18 F7 -178.7(19) . . . . ? F5' C17 C18 F7 -119(3) . . . . ? F6' C17 C18 F7 138(2) . . . . ? F5 C17 C18 F7 -71.6(16) . . . . ? C16 C17 C18 F7 37.1(18) . . . . ? F6 C17 C18 F8 71(2) . . . . ? F5' C17 C18 F8 130(3) . . . . ? F6' C17 C18 F8 28(2) . . . . ? F5 C17 C18 F8 178.2(15) . . . . ? C16 C17 C18 F8 -73.2(16) . . . . ? F6 C17 C18 F7' -126(2) . . . . ? F5' C17 C18 F7' -67(3) . . . . ? F6' C17 C18 F7' -169(2) . . . . ? F5 C17 C18 F7' -19.3(17) . . . . ? C16 C17 C18 F7' 89.3(17) . . . . ? F6 C17 C18 C19 -43(2) . . . . ? F5' C17 C18 C19 16(3) . . . . ? F6' C17 C18 C19 -86(2) . . . . ? F5 C17 C18 C19 63.7(16) . . . . ? C16 C17 C18 C19 172.3(12) . . . . ? F8' C18 C19 F10 -152(3) . . . . ? F7 C18 C19 F10 166(2) . . . . ? F8 C18 C19 F10 -81(2) . . . . ? F7' C18 C19 F10 115(2) . . . . ? C17 C18 C19 F10 32(2) . . . . ? F8' C18 C19 F10' -121(4) . . . . ? F7 C18 C19 F10' -163(3) . . . . ? F8 C18 C19 F10' -50(3) . . . . ? F7' C18 C19 F10' 146(3) . . . . ? C17 C18 C19 F10' 63(3) . . . . ? F8' C18 C19 F9' 104(4) . . . . ? F7 C18 C19 F9' 62(3) . . . . ? F8 C18 C19 F9' 175(3) . . . . ? F7' C18 C19 F9' 10(3) . . . . ? C17 C18 C19 F9' -72(3) . . . . ? F8' C18 C19 F9 92(3) . . . . ? F7 C18 C19 F9 50(2) . . . . ? F8 C18 C19 F9 163.4(19) . . . . ? F7' C18 C19 F9 -1(2) . . . . ? C17 C18 C19 F9 -83.8(19) . . . . ? F8' C18 C19 C20 -14(3) . . . . ? F7 C18 C19 C20 -56(2) . . . . ? F8 C18 C19 C20 57.1(19) . . . . ? F7' C18 C19 C20 -107(2) . . . . ? C17 C18 C19 C20 169.9(14) . . . . ? F10 C19 C20 F11' 162(3) . . . . ? F10' C19 C20 F11' 126(3) . . . . ? F9' C19 C20 F11' -113(4) . . . . ? F9 C19 C20 F11' -77(3) . . . . ? C18 C19 C20 F11' 25(3) . . . . ? F10 C19 C20 F12 86(3) . . . . ? F10' C19 C20 F12 50(3) . . . . ? F9' C19 C20 F12 171(3) . . . . ? F9 C19 C20 F12 -153(2) . . . . ? C18 C19 C20 F12 -52(3) . . . . ? F10 C19 C20 F11 -162(2) . . . . ? F10' C19 C20 F11 162(3) . . . . ? F9' C19 C20 F11 -77(3) . . . . ? F9 C19 C20 F11 -41(2) . . . . ? C18 C19 C20 F11 60(2) . . . . ? F10 C19 C20 F12' 52(3) . . . . ? F10' C19 C20 F12' 17(3) . . . . ? F9' C19 C20 F12' 138(3) . . . . ? F9 C19 C20 F12' 173(3) . . . . ? C18 C19 C20 F12' -85(3) . . . . ? F10 C19 C20 C21 -42(3) . . . . ? F10' C19 C20 C21 -77(3) . . . . ? F9' C19 C20 C21 44(3) . . . . ? F9 C19 C20 C21 79(2) . . . . ? C18 C19 C20 C21 -178.9(15) . . . . ? F11' C20 C21 F13' 127(4) . . . . ? F12 C20 C21 F13' -164(3) . . . . ? F11 C20 C21 F13' 94(3) . . . . ? F12' C20 C21 F13' -124(4) . . . . ? C19 C20 C21 F13' -29(3) . . . . ? F11' C20 C21 F14 -159(3) . . . . ? F12 C20 C21 F14 -90(3) . . . . ? F11 C20 C21 F14 168(2) . . . . ? F12' C20 C21 F14 -50(3) . . . . ? C19 C20 C21 F14 46(3) . . . . ? F11' C20 C21 F14' -116(4) . . . . ? F12 C20 C21 F14' -47(3) . . . . ? F11 C20 C21 F14' -149(3) . . . . ? F12' C20 C21 F14' -7(3) . . . . ? C19 C20 C21 F14' 89(3) . . . . ? F11' C20 C21 F13 74(3) . . . . ? F12 C20 C21 F13 144(2) . . . . ? F11 C20 C21 F13 42(2) . . . . ? F12' C20 C21 F13 -177(3) . . . . ? C19 C20 C21 F13 -81(2) . . . . ? F11' C20 C21 C22 -21(4) . . . . ? F12 C20 C21 C22 49(3) . . . . ? F11 C20 C21 C22 -53(3) . . . . ? F12' C20 C21 C22 88(3) . . . . ? C19 C20 C21 C22 -175.9(19) . . . . ? F13' C21 C22 F16 36(4) . . . . ? F14 C21 C22 F16 -33(3) . . . . ? F14' C21 C22 F16 -80(3) . . . . ? F13 C21 C22 F16 87(3) . . . . ? C20 C21 C22 F16 -175(2) . . . . ? F13' C21 C22 F17' -129(5) . . . . ? F14 C21 C22 F17' 162(4) . . . . ? F14' C21 C22 F17' 115(5) . . . . ? F13 C21 C22 F17' -78(4) . . . . ? C20 C21 C22 F17' 20(5) . . . . ? F13' C21 C22 F15 -100(3) . . . . ? F14 C21 C22 F15 -169(2) . . . . ? F14' C21 C22 F15 144(3) . . . . ? F13 C21 C22 F15 -48(2) . . . . ? C20 C21 C22 F15 49(3) . . . . ? F13' C21 C22 F16' 81(4) . . . . ? F14 C21 C22 F16' 13(3) . . . . ? F14' C21 C22 F16' -34(3) . . . . ? F13 C21 C22 F16' 133(3) . . . . ? C20 C21 C22 F16' -129(3) . . . . ? F13' C21 C22 F17 150(3) . . . . ? F14 C21 C22 F17 81(3) . . . . ? F14' C21 C22 F17 34(3) . . . . ? F13 C21 C22 F17 -158(2) . . . . ? C20 C21 C22 F17 -61(3) . . . . ? F13' C21 C22 F15' -18(3) . . . . ? F14 C21 C22 F15' -87(3) . . . . ? F14' C21 C22 F15' -134(3) . . . . ? F13 C21 C22 F15' 33(3) . . . . ? C20 C21 C22 F15' 131(3) . . . . ? F11' C20 F12' F14' 130(4) . . . . ? F12 C20 F12' F14' 115(5) . . . . ? F11 C20 F12' F14' 122(4) . . . . ? C19 C20 F12' F14' -111(3) . . . . ? C21 C20 F12' F14' 6(3) . . . . ? F13' C21 F14' F12' 127(3) . . . . ? F14 C21 F14' F12' 132(4) . . . . ? F13 C21 F14' F12' 135(11) . . . . ? C22 C21 F14' F12' -118(3) . . . . ? C20 C21 F14' F12' 6(3) . . . . ? F13' C21 F14' F16' -89(3) . . . . ? F14 C21 F14' F16' -84(3) . . . . ? F13 C21 F14' F16' -81(12) . . . . ? C22 C21 F14' F16' 26(2) . . . . ? C20 C21 F14' F16' 151(2) . . . . ? C20 F12' F14' C21 -7(3) . . . . ? C20 F12' F14' F16' -73(5) . . . . ? F16 C22 F16' F14' 162(4) . . . . ? F17' C22 F16' F14' -123(5) . . . . ? F15 C22 F16' F14' -149(12) . . . . ? F17 C22 F16' F14' -84(3) . . . . ? F15' C22 F16' F14' 119(3) . . . . ? C21 C22 F16' F14' 27(2) . . . . ? C21 F14' F16' C22 -28(3) . . . . ? F12' F14' F16' C22 41(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O4 0.852(11) 2.52(12) 2.755(14) 97(9) 4_576 O1 H1B O3 0.851(11) 1.80(3) 2.64(2) 171(13) 1_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.228 _refine_diff_density_min -1.510 _refine_diff_density_rms 0.166 # Attachment '- SBiCl-compound 1 (CCDC724767).cif' #============================================================================== # Formatted by publCIF data_wy1909wm _database_code_depnum_ccdc_archive 'CCDC 820464' #TrackingRef '- SBiCl-compound 1 (CCDC724767).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Bi Cl S' _chemical_formula_weight 456.73 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9590(6) _cell_length_b 9.0096(6) _cell_length_c 34.274(3) _cell_angle_alpha 93.165(2) _cell_angle_beta 93.3060(10) _cell_angle_gamma 90.1870(10) _cell_volume 2757.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13143 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 13.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3954 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ; _diffrn_ambient_temperature 293(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 'Smart CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13143 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9349 _reflns_number_gt 7386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction SAINT _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^)+(0.0998P)^2^+15.6265P] 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 9349 _refine_ls_number_parameters 613 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.19188(6) 0.27426(6) 0.372892(17) 0.03933(17) Uani 1 1 d . . . Bi2 Bi 0.72489(6) 0.30590(6) 0.128965(17) 0.03952(16) Uani 1 1 d . . . Bi3 Bi 0.22441(6) 0.24570(6) 0.128517(17) 0.03991(17) Uani 1 1 d . . . Bi4 Bi 0.25444(6) 0.77448(6) 0.371640(18) 0.04192(17) Uani 1 1 d . . . C1 C 0.1792(18) 0.4488(16) 0.4218(4) 0.042(3) Uani 1 1 d . . . C2 C 0.310(3) 0.4936(19) 0.4441(5) 0.064(5) Uani 1 1 d . . . H2 H 0.4002 0.4525 0.4372 0.077 Uiso 1 1 calc R . . C3 C 0.311(3) 0.596(2) 0.4760(6) 0.086(7) Uani 1 1 d . . . H3 H 0.3986 0.6248 0.4902 0.103 Uiso 1 1 calc R . . C4 C 0.171(3) 0.653(2) 0.4854(7) 0.087(8) Uani 1 1 d . . . H4 H 0.1672 0.7231 0.5062 0.105 Uiso 1 1 calc R . . C5 C 0.037(3) 0.609(2) 0.4650(6) 0.074(6) Uani 1 1 d . . . H5 H -0.0534 0.6463 0.4731 0.088 Uiso 1 1 calc R . . C6 C 0.039(2) 0.5096(18) 0.4331(5) 0.058(5) Uani 1 1 d . . . C7 C -0.099(2) 0.4679(18) 0.4119(5) 0.058(4) Uani 1 1 d . . . H7A H -0.1110 0.5247 0.3887 0.069 Uiso 1 1 calc R . . H7B H -0.1820 0.4920 0.4282 0.069 Uiso 1 1 calc R . . C8 C -0.1850(18) 0.262(2) 0.3472(6) 0.070(6) Uani 1 1 d . . . H8A H -0.1802 0.1614 0.3359 0.084 Uiso 1 1 calc R . . H8B H -0.2892 0.2910 0.3471 0.084 Uiso 1 1 calc R . . C9 C -0.0989(17) 0.3676(18) 0.3225(5) 0.051(4) Uani 1 1 d . . . C10 C -0.185(2) 0.435(3) 0.2934(6) 0.076(6) Uani 1 1 d . . . H10 H -0.2876 0.4183 0.2907 0.091 Uiso 1 1 calc R . . C11 C -0.117(4) 0.529(3) 0.2681(7) 0.102(10) Uani 1 1 d . . . H11 H -0.1744 0.5786 0.2495 0.123 Uiso 1 1 calc R . . C12 C 0.039(3) 0.544(3) 0.2717(6) 0.094(8) Uani 1 1 d . . . H12 H 0.0872 0.6019 0.2545 0.113 Uiso 1 1 calc R . . C13 C 0.122(2) 0.4742(19) 0.3008(5) 0.057(4) Uani 1 1 d . . . H13 H 0.2253 0.4862 0.3032 0.069 Uiso 1 1 calc R . . C14 C 0.0535(17) 0.3892(17) 0.3254(4) 0.044(4) Uani 1 1 d . . . C15 C 0.6033(17) 0.4400(15) 0.1746(4) 0.041(3) Uani 1 1 d . . . C16 C 0.5169(18) 0.375(2) 0.2017(5) 0.056(4) Uani 1 1 d . . . H16A H 0.5060 0.2725 0.2005 0.067 Uiso 1 1 calc R . . C17 C 0.449(2) 0.457(3) 0.2296(6) 0.079(6) Uani 1 1 d . . . H17A H 0.3931 0.4097 0.2474 0.095 Uiso 1 1 calc R . . C18 C 0.461(2) 0.611(3) 0.2319(7) 0.081(7) Uani 1 1 d . . . H18A H 0.4096 0.6667 0.2504 0.097 Uiso 1 1 calc R . . C19 C 0.550(2) 0.683(2) 0.2062(5) 0.069(6) Uani 1 1 d . . . H19A H 0.5573 0.7857 0.2077 0.082 Uiso 1 1 calc R . . C20 C 0.6275(17) 0.5987(16) 0.1782(5) 0.044(4) Uani 1 1 d . . . C21 C 0.727(2) 0.6749(19) 0.1542(5) 0.063(5) Uani 1 1 d . . . H21A H 0.8276 0.6707 0.1661 0.076 Uiso 1 1 calc R . . H21B H 0.6986 0.7787 0.1541 0.076 Uiso 1 1 calc R . . C22 C 0.5329(19) 0.599(2) 0.0889(5) 0.063(5) Uani 1 1 d . . . H22A H 0.4747 0.6089 0.1119 0.075 Uiso 1 1 calc R . . H22B H 0.5094 0.6823 0.0729 0.075 Uiso 1 1 calc R . . C23 C 0.4927(18) 0.454(2) 0.0658(5) 0.053(4) Uani 1 1 d . . . C24 C 0.390(2) 0.453(3) 0.0336(6) 0.075(6) Uani 1 1 d . . . H24A H 0.3475 0.5412 0.0257 0.090 Uiso 1 1 calc R . . C25 C 0.352(2) 0.320(3) 0.0135(6) 0.084(7) Uani 1 1 d . . . H25A H 0.2855 0.3196 -0.0084 0.100 Uiso 1 1 calc R . . C26 C 0.410(2) 0.188(3) 0.0254(5) 0.065(5) Uani 1 1 d . . . H26A H 0.3836 0.0993 0.0116 0.078 Uiso 1 1 calc R . . C27 C 0.507(2) 0.188(2) 0.0575(5) 0.061(5) Uani 1 1 d . . . H27A H 0.5458 0.0983 0.0654 0.074 Uiso 1 1 calc R . . C28 C 0.5492(14) 0.3168(17) 0.0787(4) 0.040(3) Uani 1 1 d . . . C29 C 0.0452(17) 0.219(2) 0.0783(5) 0.050(4) Uani 1 1 d . . . C30 C 0.0101(17) 0.343(2) 0.0596(5) 0.061(5) Uani 1 1 d . . . H30A H 0.0507 0.4354 0.0680 0.073 Uiso 1 1 calc R . . C31 C -0.094(2) 0.325(3) 0.0255(6) 0.073(6) Uani 1 1 d . . . H31A H -0.1256 0.4072 0.0119 0.088 Uiso 1 1 calc R . . C32 C -0.147(2) 0.183(4) 0.0137(6) 0.090(8) Uani 1 1 d . . . H32A H -0.2119 0.1713 -0.0085 0.108 Uiso 1 1 calc R . . C33 C -0.107(2) 0.063(3) 0.0333(6) 0.072(6) Uani 1 1 d . . . H33A H -0.1458 -0.0301 0.0250 0.086 Uiso 1 1 calc R . . C34 C -0.0093(16) 0.078(2) 0.0654(5) 0.055(4) Uani 1 1 d . . . C35 C 0.030(2) -0.062(2) 0.0860(5) 0.061(5) Uani 1 1 d . . . H35A H 0.0059 -0.1482 0.0687 0.073 Uiso 1 1 calc R . . H35B H -0.0280 -0.0673 0.1090 0.073 Uiso 1 1 calc R . . C36 C 0.236(2) -0.1203(18) 0.1504(5) 0.056(4) Uani 1 1 d . . . H36A H 0.2081 -0.2245 0.1496 0.067 Uiso 1 1 calc R . . H36B H 0.3375 -0.1110 0.1619 0.067 Uiso 1 1 calc R . . C37 C 0.1317(16) -0.0316(16) 0.1761(4) 0.040(3) Uani 1 1 d . . . C38 C 0.0647(19) -0.109(2) 0.2046(5) 0.058(4) Uani 1 1 d . . . H38A H 0.0795 -0.2103 0.2061 0.069 Uiso 1 1 calc R . . C39 C -0.025(2) -0.032(2) 0.2311(6) 0.070(5) Uani 1 1 d . . . H39A H -0.0738 -0.0842 0.2493 0.084 Uiso 1 1 calc R . . C40 C -0.042(2) 0.112(2) 0.2305(5) 0.065(5) Uani 1 1 d . . . H40A H -0.0961 0.1614 0.2496 0.078 Uiso 1 1 calc R . . C41 C 0.022(2) 0.193(2) 0.2011(5) 0.058(5) Uani 1 1 d . . . H41A H 0.0083 0.2954 0.2006 0.070 Uiso 1 1 calc R . . C42 C 0.1039(15) 0.1187(16) 0.1730(5) 0.043(3) Uani 1 1 d . . . C43 C 0.2873(19) 0.9474(16) 0.4205(5) 0.048(4) Uani 1 1 d . . . C44 C 0.164(2) 0.9913(16) 0.4425(5) 0.056(4) Uani 1 1 d . . . H44A H 0.0697 0.9517 0.4359 0.067 Uiso 1 1 calc R . . C45 C 0.187(3) 1.096(2) 0.4745(6) 0.087(8) Uani 1 1 d . . . H45A H 0.1038 1.1273 0.4877 0.105 Uiso 1 1 calc R . . C46 C 0.322(3) 1.153(2) 0.4872(7) 0.086(7) Uani 1 1 d . . . H46A H 0.3331 1.2181 0.5092 0.103 Uiso 1 1 calc R . . C47 C 0.445(3) 1.109(2) 0.4659(6) 0.072(6) Uani 1 1 d . . . H47A H 0.5390 1.1497 0.4732 0.087 Uiso 1 1 calc R . . C48 C 0.431(2) 1.0042(17) 0.4337(5) 0.056(4) Uani 1 1 d . . . C49 C 0.564(2) 0.962(2) 0.4117(5) 0.062(5) Uani 1 1 d . . . H49A H 0.6540 0.9868 0.4278 0.074 Uiso 1 1 calc R . . H49B H 0.5648 1.0185 0.3884 0.074 Uiso 1 1 calc R . . C50 C 0.6130(18) 0.7637(18) 0.3466(6) 0.058(4) Uani 1 1 d . . . H50A H 0.7184 0.7878 0.3460 0.069 Uiso 1 1 calc R . . H50B H 0.5978 0.6640 0.3348 0.069 Uiso 1 1 calc R . . C51 C 0.5257(18) 0.8689(16) 0.3230(5) 0.047(4) Uani 1 1 d . . . C52 C 0.603(2) 0.942(2) 0.2932(5) 0.056(4) Uani 1 1 d . . . H52A H 0.7048 0.9281 0.2912 0.067 Uiso 1 1 calc R . . C53 C 0.527(2) 1.031(2) 0.2680(5) 0.064(5) Uani 1 1 d . . . H53A H 0.5763 1.0810 0.2494 0.077 Uiso 1 1 calc R . . C54 C 0.382(3) 1.045(2) 0.2709(5) 0.069(6) Uani 1 1 d . . . H54A H 0.3299 1.0995 0.2524 0.083 Uiso 1 1 calc R . . C55 C 0.3010(18) 0.9836(18) 0.2998(5) 0.049(4) Uani 1 1 d . . . H55A H 0.1999 1.0040 0.3017 0.059 Uiso 1 1 calc R . . C56 C 0.3757(16) 0.8904(15) 0.3260(4) 0.040(3) Uani 1 1 d . . . Cl1 Cl 0.4399(4) 0.4017(5) 0.35361(16) 0.0695(13) Uani 1 1 d . . . Cl2 Cl 0.5964(5) 0.0587(4) 0.14839(15) 0.0638(12) Uani 1 1 d . . . Cl3 Cl 0.0927(6) 0.4982(4) 0.15039(15) 0.0662(12) Uani 1 1 d . . . Cl4 Cl -0.0008(4) 0.9048(6) 0.35104(16) 0.0690(13) Uani 1 1 d . . . S1 S -0.1062(5) 0.2685(5) 0.39728(15) 0.0593(11) Uani 1 1 d . . . S2 S 0.7300(5) 0.6018(5) 0.10357(14) 0.0545(10) Uani 1 1 d . . . S3 S 0.2327(5) -0.0592(4) 0.10079(13) 0.0520(10) Uani 1 1 d . . . S4 S 0.5629(5) 0.7657(5) 0.39761(14) 0.0537(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0381(3) 0.0310(3) 0.0493(4) 0.0048(2) 0.0026(2) 0.0077(2) Bi2 0.0336(3) 0.0336(3) 0.0515(4) 0.0032(2) 0.0026(2) 0.0060(2) Bi3 0.0337(3) 0.0346(3) 0.0515(4) 0.0056(2) 0.0011(2) -0.0045(2) Bi4 0.0383(3) 0.0318(3) 0.0559(4) 0.0025(2) 0.0051(2) -0.0044(2) C1 0.064(10) 0.040(8) 0.024(8) 0.007(6) -0.004(7) 0.005(7) C2 0.101(15) 0.044(9) 0.048(11) -0.001(8) 0.008(10) -0.011(9) C3 0.14(2) 0.063(13) 0.056(13) 0.021(11) -0.026(13) -0.020(13) C4 0.14(2) 0.032(10) 0.097(18) -0.009(10) 0.047(17) -0.013(12) C5 0.116(18) 0.039(10) 0.070(14) 0.010(9) 0.037(13) 0.003(11) C6 0.072(12) 0.042(9) 0.063(12) 0.004(8) 0.029(9) -0.002(8) C7 0.069(11) 0.050(10) 0.055(11) 0.001(8) 0.016(9) 0.015(8) C8 0.036(9) 0.084(13) 0.084(14) -0.023(11) -0.022(8) 0.009(9) C9 0.038(8) 0.049(9) 0.063(11) -0.016(8) -0.008(7) 0.011(7) C10 0.069(13) 0.085(15) 0.066(14) -0.028(12) -0.024(10) 0.024(11) C11 0.14(2) 0.104(19) 0.056(15) -0.004(13) -0.041(15) 0.062(18) C12 0.14(2) 0.094(17) 0.047(13) 0.026(12) 0.008(14) 0.031(16) C13 0.078(12) 0.051(10) 0.042(10) -0.006(8) 0.005(9) 0.004(9) C14 0.049(8) 0.054(9) 0.029(8) 0.005(7) -0.001(6) 0.025(7) C15 0.052(8) 0.030(7) 0.039(9) -0.003(6) 0.002(7) -0.005(6) C16 0.048(9) 0.074(12) 0.047(10) 0.007(9) 0.006(7) 0.009(8) C17 0.078(14) 0.092(16) 0.067(14) -0.026(12) 0.015(11) 0.001(12) C18 0.060(12) 0.103(17) 0.077(15) -0.037(13) 0.011(11) 0.011(11) C19 0.091(14) 0.068(12) 0.044(11) -0.013(9) -0.015(10) 0.045(11) C20 0.050(9) 0.031(7) 0.050(10) -0.001(7) -0.014(7) 0.016(6) C21 0.071(12) 0.044(9) 0.071(13) -0.009(9) -0.020(9) 0.007(8) C22 0.058(10) 0.069(12) 0.063(12) 0.027(10) 0.002(9) 0.023(9) C23 0.049(9) 0.076(12) 0.036(9) 0.018(8) 0.002(7) 0.000(8) C24 0.062(11) 0.107(17) 0.061(13) 0.040(13) -0.003(10) -0.002(11) C25 0.061(12) 0.14(2) 0.050(12) 0.018(14) -0.021(9) -0.033(13) C26 0.051(10) 0.096(15) 0.046(11) -0.003(10) 0.001(8) -0.011(10) C27 0.059(10) 0.087(14) 0.039(10) -0.003(9) 0.015(8) 0.003(10) C28 0.028(7) 0.052(9) 0.040(9) 0.014(7) -0.004(6) 0.013(6) C29 0.044(8) 0.068(11) 0.038(9) 0.008(8) 0.000(7) -0.001(8) C30 0.036(8) 0.091(14) 0.061(12) 0.027(10) 0.008(8) 0.018(8) C31 0.059(11) 0.110(18) 0.054(12) 0.016(12) 0.011(9) 0.017(12) C32 0.059(12) 0.16(3) 0.045(12) 0.005(15) -0.007(9) 0.010(15) C33 0.056(11) 0.094(15) 0.062(13) -0.025(12) 0.010(9) 0.008(11) C34 0.027(7) 0.076(12) 0.058(11) -0.023(9) 0.010(7) -0.004(7) C35 0.066(11) 0.060(11) 0.056(12) -0.001(9) 0.003(9) -0.010(9) C36 0.065(10) 0.042(9) 0.062(12) 0.013(8) 0.005(8) 0.011(8) C37 0.040(7) 0.036(7) 0.043(9) 0.002(6) -0.007(6) -0.009(6) C38 0.061(10) 0.053(10) 0.061(12) 0.021(9) 0.003(8) -0.014(8) C39 0.083(13) 0.078(14) 0.053(12) 0.012(10) 0.026(10) -0.019(11) C40 0.077(12) 0.079(13) 0.040(10) -0.003(9) 0.009(9) 0.025(10) C41 0.072(11) 0.054(10) 0.047(10) -0.019(8) 0.012(8) -0.020(9) C42 0.030(7) 0.040(8) 0.059(10) -0.002(7) 0.004(6) 0.003(6) C43 0.061(10) 0.037(8) 0.048(10) 0.017(7) 0.006(8) 0.007(7) C44 0.069(11) 0.032(8) 0.068(12) 0.010(8) 0.016(9) 0.005(7) C45 0.16(3) 0.057(12) 0.040(11) -0.002(10) 0.006(13) 0.043(15) C46 0.13(2) 0.062(13) 0.064(15) -0.006(11) -0.026(14) 0.019(13) C47 0.107(16) 0.045(10) 0.059(13) -0.007(9) -0.026(11) 0.002(10) C48 0.080(12) 0.033(8) 0.056(11) 0.013(8) -0.012(9) -0.003(8) C49 0.073(12) 0.058(11) 0.053(11) 0.014(9) -0.024(9) -0.017(9) C50 0.043(9) 0.044(9) 0.084(13) -0.010(9) 0.009(8) 0.000(7) C51 0.057(9) 0.032(7) 0.052(10) -0.010(7) 0.006(7) -0.031(7) C52 0.052(9) 0.067(11) 0.050(11) 0.002(9) 0.004(8) -0.020(8) C53 0.070(12) 0.077(13) 0.044(11) -0.007(9) 0.012(9) -0.022(10) C54 0.111(17) 0.063(12) 0.033(10) 0.018(9) -0.027(10) -0.003(11) C55 0.047(9) 0.056(10) 0.044(10) -0.004(8) 0.001(7) -0.007(7) C56 0.048(8) 0.031(7) 0.040(9) -0.005(6) -0.008(6) 0.000(6) Cl1 0.037(2) 0.063(3) 0.110(4) -0.003(3) 0.022(2) 0.0002(18) Cl2 0.070(3) 0.0300(19) 0.092(4) 0.015(2) -0.001(2) 0.0010(18) Cl3 0.078(3) 0.0282(19) 0.089(4) -0.007(2) -0.013(2) 0.0050(18) Cl4 0.0286(18) 0.078(3) 0.099(4) -0.003(3) -0.002(2) 0.0015(18) S1 0.055(2) 0.053(2) 0.073(3) 0.011(2) 0.019(2) -0.0001(19) S2 0.051(2) 0.048(2) 0.066(3) 0.013(2) 0.004(2) -0.0028(18) S3 0.053(2) 0.044(2) 0.060(3) -0.0054(19) 0.0146(19) 0.0020(17) S4 0.053(2) 0.046(2) 0.062(3) 0.014(2) -0.0084(19) 0.0044(18) _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 2.242(15) . ? Bi1 C14 2.285(14) . ? Bi1 Cl1 2.632(4) . ? Bi1 S1 2.845(4) . ? Bi2 C15 2.256(14) . ? Bi2 C28 2.273(14) . ? Bi2 Cl2 2.638(4) . ? Bi2 S2 2.851(4) . ? Bi3 C42 2.275(15) . ? Bi3 C29 2.287(16) . ? Bi3 Cl3 2.657(4) . ? Bi3 S3 2.860(4) . ? Bi4 C43 2.229(17) . ? Bi4 C56 2.255(15) . ? Bi4 Cl4 2.651(4) . ? Bi4 S4 2.857(4) . ? C1 C2 1.41(3) . ? C1 C6 1.44(2) . ? C2 C3 1.39(3) . ? C2 H2 0.9300 . ? C3 C4 1.40(3) . ? C3 H3 0.9300 . ? C4 C5 1.40(3) . ? C4 H4 0.9300 . ? C5 C6 1.37(3) . ? C5 H5 0.9300 . ? C6 C7 1.44(3) . ? C7 S1 1.838(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.54(3) . ? C8 S1 1.815(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.38(2) . ? C9 C10 1.39(3) . ? C10 C11 1.40(4) . ? C10 H10 0.9300 . ? C11 C12 1.41(4) . ? C11 H11 0.9300 . ? C12 C13 1.39(3) . ? C12 H12 0.9300 . ? C13 C14 1.34(2) . ? C13 H13 0.9300 . ? C15 C16 1.39(2) . ? C15 C20 1.44(2) . ? C16 C17 1.35(2) . ? C16 H16A 0.9300 . ? C17 C18 1.39(3) . ? C17 H17A 0.9300 . ? C18 C19 1.40(3) . ? C18 H18A 0.9300 . ? C19 C20 1.41(2) . ? C19 H19A 0.9300 . ? C20 C21 1.44(2) . ? C21 S2 1.822(19) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.52(3) . ? C22 S2 1.808(18) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.40(3) . ? C23 C28 1.42(2) . ? C24 C25 1.38(3) . ? C24 H24A 0.9300 . ? C25 C26 1.37(3) . ? C25 H25A 0.9300 . ? C26 C27 1.36(3) . ? C26 H26A 0.9300 . ? C27 C28 1.37(2) . ? C27 H27A 0.9300 . ? C29 C30 1.35(2) . ? C29 C34 1.39(2) . ? C30 C31 1.45(3) . ? C30 H30A 0.9300 . ? C31 C32 1.39(3) . ? C31 H31A 0.9300 . ? C32 C33 1.35(3) . ? C32 H32A 0.9300 . ? C33 C34 1.37(3) . ? C33 H33A 0.9300 . ? C34 C35 1.51(3) . ? C35 S3 1.859(19) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.52(2) . ? C36 S3 1.813(17) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C42 1.39(2) . ? C37 C38 1.39(2) . ? C38 C39 1.40(3) . ? C38 H38A 0.9300 . ? C39 C40 1.30(3) . ? C39 H39A 0.9300 . ? C40 C41 1.42(2) . ? C40 H40A 0.9300 . ? C41 C42 1.39(2) . ? C41 H41A 0.9300 . ? C43 C44 1.42(2) . ? C43 C48 1.42(2) . ? C44 C45 1.41(3) . ? C44 H44A 0.9300 . ? C45 C46 1.35(4) . ? C45 H45A 0.9300 . ? C46 C47 1.40(3) . ? C46 H46A 0.9300 . ? C47 C48 1.41(3) . ? C47 H47A 0.9300 . ? C48 C49 1.49(3) . ? C49 S4 1.807(19) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.48(2) . ? C50 S4 1.829(19) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C56 1.37(2) . ? C51 C52 1.45(2) . ? C52 C53 1.37(3) . ? C52 H52A 0.9300 . ? C53 C54 1.31(3) . ? C53 H53A 0.9300 . ? C54 C55 1.40(2) . ? C54 H54A 0.9300 . ? C55 C56 1.41(2) . ? C55 H55A 0.9300 . ? 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 C14 98.9(5) . . ? C1 Bi1 Cl1 88.4(4) . . ? C14 Bi1 Cl1 91.8(4) . . ? C1 Bi1 S1 73.3(4) . . ? C14 Bi1 S1 75.2(4) . . ? Cl1 Bi1 S1 155.23(13) . . ? C15 Bi2 C28 98.0(5) . . ? C15 Bi2 Cl2 91.0(4) . . ? C28 Bi2 Cl2 88.4(4) . . ? C15 Bi2 S2 75.7(4) . . ? C28 Bi2 S2 73.1(4) . . ? Cl2 Bi2 S2 155.12(13) . . ? C42 Bi3 C29 97.4(5) . . ? C42 Bi3 Cl3 91.7(4) . . ? C29 Bi3 Cl3 87.8(4) . . ? C42 Bi3 S3 74.8(4) . . ? C29 Bi3 S3 73.8(5) . . ? Cl3 Bi3 S3 155.18(14) . . ? C43 Bi4 C56 98.2(5) . . ? C43 Bi4 Cl4 88.4(4) . . ? C56 Bi4 Cl4 91.6(4) . . ? C43 Bi4 S4 73.4(4) . . ? C56 Bi4 S4 75.1(4) . . ? Cl4 Bi4 S4 155.34(14) . . ? C2 C1 C6 118.2(15) . . ? C2 C1 Bi1 119.8(12) . . ? C6 C1 Bi1 121.8(12) . . ? C3 C2 C1 124(2) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 116(2) . . ? C2 C3 H3 122.1 . . ? C4 C3 H3 122.1 . . ? C5 C4 C3 123(2) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C6 C5 C4 120(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 119.5(18) . . ? C5 C6 C1 119(2) . . ? C7 C6 C1 121.3(16) . . ? C6 C7 S1 112.0(12) . . ? C6 C7 H7A 109.2 . . ? S1 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? S1 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 S1 110.7(12) . . ? C9 C8 H8A 109.5 . . ? S1 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C14 C9 C10 119.6(18) . . ? C14 C9 C8 124.9(15) . . ? C10 C9 C8 115.3(16) . . ? C9 C10 C11 120(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 118(2) . . ? C10 C11 H11 121.0 . . ? C12 C11 H11 121.0 . . ? C13 C12 C11 120(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 121.5(16) . . ? C13 C14 Bi1 119.7(13) . . ? C9 C14 Bi1 118.8(12) . . ? C16 C15 C20 118.5(14) . . ? C16 C15 Bi2 122.9(11) . . ? C20 C15 Bi2 118.3(10) . . ? C17 C16 C15 122.2(19) . . ? C17 C16 H16A 118.9 . . ? C15 C16 H16A 118.9 . . ? C16 C17 C18 121(2) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C17 C18 C19 120.0(18) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 120.2(18) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C19 C20 C15 118.2(16) . . ? C19 C20 C21 118.8(16) . . ? C15 C20 C21 123.0(14) . . ? C20 C21 S2 115.4(12) . . ? C20 C21 H21A 108.4 . . ? S2 C21 H21A 108.4 . . ? C20 C21 H21B 108.4 . . ? S2 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? C23 C22 S2 109.7(11) . . ? C23 C22 H22A 109.7 . . ? S2 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? S2 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C24 C23 C28 119.2(18) . . ? C24 C23 C22 120.1(17) . . ? C28 C23 C22 120.6(14) . . ? C25 C24 C23 119(2) . . ? C25 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C26 C25 C24 121.0(18) . . ? C26 C25 H25A 119.5 . . ? C24 C25 H25A 119.5 . . ? C27 C26 C25 120(2) . . ? C27 C26 H26A 120.2 . . ? C25 C26 H26A 120.2 . . ? C26 C27 C28 122.1(19) . . ? C26 C27 H27A 119.0 . . ? C28 C27 H27A 119.0 . . ? C27 C28 C23 118.6(15) . . ? C27 C28 Bi2 119.0(11) . . ? C23 C28 Bi2 122.1(12) . . ? C30 C29 C34 123.0(17) . . ? C30 C29 Bi3 115.8(13) . . ? C34 C29 Bi3 120.8(12) . . ? C29 C30 C31 116(2) . . ? C29 C30 H30A 121.8 . . ? C31 C30 H30A 121.8 . . ? C32 C31 C30 119(2) . . ? C32 C31 H31A 120.6 . . ? C30 C31 H31A 120.6 . . ? C33 C32 C31 122(2) . . ? C33 C32 H32A 119.0 . . ? C31 C32 H32A 119.0 . . ? C32 C33 C34 120(2) . . ? C32 C33 H33A 120.2 . . ? C34 C33 H33A 120.2 . . ? C33 C34 C29 119.9(19) . . ? C33 C34 C35 116.7(17) . . ? C29 C34 C35 123.4(16) . . ? C34 C35 S3 109.2(11) . . ? C34 C35 H35A 109.8 . . ? S3 C35 H35A 109.8 . . ? C34 C35 H35B 109.8 . . ? S3 C35 H35B 109.8 . . ? H35A C35 H35B 108.3 . . ? C37 C36 S3 112.8(11) . . ? C37 C36 H36A 109.0 . . ? S3 C36 H36A 109.0 . . ? C37 C36 H36B 109.0 . . ? S3 C36 H36B 109.0 . . ? H36A C36 H36B 107.8 . . ? C42 C37 C38 119.7(15) . . ? C42 C37 C36 123.8(13) . . ? C38 C37 C36 116.5(14) . . ? C37 C38 C39 119.6(16) . . ? C37 C38 H38A 120.2 . . ? C39 C38 H38A 120.2 . . ? C40 C39 C38 121.1(16) . . ? C40 C39 H39A 119.4 . . ? C38 C39 H39A 119.4 . . ? C39 C40 C41 120.6(16) . . ? C39 C40 H40A 119.7 . . ? C41 C40 H40A 119.7 . . ? C42 C41 C40 119.5(17) . . ? C42 C41 H41A 120.3 . . ? C40 C41 H41A 120.3 . . ? C37 C42 C41 119.1(15) . . ? C37 C42 Bi3 119.3(10) . . ? C41 C42 Bi3 120.9(11) . . ? C44 C43 C48 117.5(17) . . ? C44 C43 Bi4 119.5(13) . . ? C48 C43 Bi4 122.6(12) . . ? C45 C44 C43 119(2) . . ? C45 C44 H44A 120.3 . . ? C43 C44 H44A 120.3 . . ? C46 C45 C44 124(2) . . ? C46 C45 H45A 118.1 . . ? C44 C45 H45A 118.1 . . ? C45 C46 C47 117(2) . . ? C45 C46 H46A 121.4 . . ? C47 C46 H46A 121.4 . . ? C46 C47 C48 122(2) . . ? C46 C47 H47A 119.2 . . ? C48 C47 H47A 119.2 . . ? C47 C48 C43 120.1(18) . . ? C47 C48 C49 120.0(18) . . ? C43 C48 C49 119.7(16) . . ? C48 C49 S4 111.5(12) . . ? C48 C49 H49A 109.3 . . ? S4 C49 H49A 109.3 . . ? C48 C49 H49B 109.3 . . ? S4 C49 H49B 109.3 . . ? H49A C49 H49B 108.0 . . ? C51 C50 S4 113.6(11) . . ? C51 C50 H50A 108.9 . . ? S4 C50 H50A 108.9 . . ? C51 C50 H50B 108.9 . . ? S4 C50 H50B 108.9 . . ? H50A C50 H50B 107.7 . . ? C56 C51 C52 119.6(16) . . ? C56 C51 C50 122.9(14) . . ? C52 C51 C50 117.3(15) . . ? C53 C52 C51 120.8(17) . . ? C53 C52 H52A 119.6 . . ? C51 C52 H52A 119.6 . . ? C54 C53 C52 117.8(17) . . ? C54 C53 H53A 121.1 . . ? C52 C53 H53A 121.1 . . ? C53 C54 C55 124.9(17) . . ? C53 C54 H54A 117.5 . . ? C55 C54 H54A 117.5 . . ? C54 C55 C56 118.5(16) . . ? C54 C55 H55A 120.8 . . ? C56 C55 H55A 120.8 . . ? C51 C56 C55 118.2(14) . . ? C51 C56 Bi4 119.9(11) . . ? C55 C56 Bi4 121.9(11) . . ? C8 S1 C7 103.9(9) . . ? C8 S1 Bi1 92.5(6) . . ? C7 S1 Bi1 91.9(6) . . ? C22 S2 C21 101.2(9) . . ? C22 S2 Bi2 93.3(6) . . ? C21 S2 Bi2 90.2(6) . . ? C36 S3 C35 102.7(8) . . ? C36 S3 Bi3 91.3(6) . . ? C35 S3 Bi3 92.3(6) . . ? C49 S4 C50 102.4(8) . . ? C49 S4 Bi4 91.5(6) . . ? C50 S4 Bi4 89.3(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 Cl1 0.93 2.65 3.37(2) 134.6 . C8 H8B Cl1 0.97 2.64 3.606(17) 171.7 1_455 C16 H16A Cl2 0.93 2.71 3.401(19) 131.6 . C21 H21B Cl2 0.97 2.70 3.666(17) 174.0 1_565 C36 H36A Cl3 0.97 2.70 3.666(17) 172.2 1_545 C41 H41A Cl3 0.93 2.71 3.409(19) 132.2 . C50 H50A Cl4 0.97 2.72 3.674(17) 169.2 1_655 C55 H55A Cl4 0.93 2.72 3.401(16) 130.7 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 2.829 _refine_diff_density_min -2.213 _refine_diff_density_rms 0.230 # Attachment '- SBiClO4-compound 2 (CCDC728508).cif' data_cd29137 _database_code_depnum_ccdc_archive 'CCDC 820465' #TrackingRef '- SBiClO4-compound 2 (CCDC728508).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Bi Cl O5 S' _chemical_formula_weight 538.74 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' Cl Cl 0.1484 0.1585 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8231(17) _cell_length_b 11.7666(14) _cell_length_c 10.0447(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.639(2) _cell_angle_gamma 90.00 _cell_volume 1632.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3348 _cell_measurement_theta_min 4.548 _cell_measurement_theta_max 51.984 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.186 _exptl_crystal_size_mid 0.173 _exptl_crystal_size_min 0.168 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 11.113 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.63284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8802 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3206 _reflns_number_gt 2641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. DFIX restraints have been used for the O-H distances in water molecules. MPLA restraints have been used for the two phenyl-rings. ; _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^)+(0.0805P)^2^+3.7674P] 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 3206 _refine_ls_number_parameters 205 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Bi Bi 0.26420(3) -0.03829(3) 1.02691(4) 0.0433(2) Uani 1 1 d . . . S1 S 0.2822(2) 0.1525(3) 1.1738(3) 0.0587(8) Uani 1 1 d . . . Cl1 Cl 0.2440(3) -0.0597(3) 0.4736(3) 0.0601(8) Uani 1 1 d . . . O1 O 0.2450(9) -0.1607(8) 0.8263(8) 0.073(3) Uani 1 1 d D . . H1A H 0.242(11) -0.231(2) 0.833(13) 0.087 Uiso 1 1 d D . . H1B H 0.248(11) -0.158(11) 0.744(3) 0.087 Uiso 1 1 d D . . O2 O 0.182(2) 0.0296(19) 0.484(3) 0.192(11) Uani 1 1 d . . . O3 O 0.3383(14) -0.016(2) 0.504(2) 0.164(8) Uani 1 1 d . . . O4 O 0.2407(11) -0.1018(13) 0.3420(11) 0.107(4) Uani 1 1 d . . . O5 O 0.2281(18) -0.1554(13) 0.5563(15) 0.166(9) Uani 1 1 d . . . C1 C 0.3778(8) 0.0583(10) 0.9172(12) 0.049(3) Uani 1 1 d . . . C2 C 0.4320(9) 0.0067(12) 0.8272(13) 0.054(3) Uani 1 1 d . . . H2 H 0.4200 -0.0686 0.8036 0.065 Uiso 1 1 calc R . . C3 C 0.5048(10) 0.0655(15) 0.7705(16) 0.074(4) Uani 1 1 d . . . H3 H 0.5404 0.0295 0.7064 0.088 Uiso 1 1 calc R . . C4 C 0.5273(9) 0.1757(13) 0.8046(16) 0.071(4) Uani 1 1 d . . . H4 H 0.5783 0.2132 0.7663 0.085 Uiso 1 1 calc R . . C5 C 0.4731(10) 0.2287(12) 0.8961(15) 0.067(4) Uani 1 1 d . . . H5 H 0.4873 0.3033 0.9209 0.080 Uiso 1 1 calc R . . C6 C 0.3960(8) 0.1715(10) 0.9530(12) 0.051(3) Uani 1 1 d . . . C7 C 0.3334(10) 0.2365(10) 1.0429(14) 0.066(4) Uani 1 1 d . . . H7A H 0.2808 0.2706 0.9895 0.080 Uiso 1 1 calc R . . H7B H 0.3713 0.2976 1.0837 0.080 Uiso 1 1 calc R . . C8 C 0.1533(10) 0.1931(15) 1.1550(15) 0.075(4) Uani 1 1 d . . . H8A H 0.1185 0.1589 1.2265 0.090 Uiso 1 1 calc R . . H8B H 0.1479 0.2750 1.1632 0.090 Uiso 1 1 calc R . . C9 C 0.1066(9) 0.1563(12) 1.0223(13) 0.060(3) Uani 1 1 d . . . C10 C 0.0260(10) 0.2221(12) 0.9737(16) 0.070(4) Uani 1 1 d . . . H10 H 0.0096 0.2889 1.0167 0.085 Uiso 1 1 calc R . . C11 C -0.0277(9) 0.1859(15) 0.8620(17) 0.082(5) Uani 1 1 d . . . H11 H -0.0833 0.2253 0.8340 0.098 Uiso 1 1 calc R . . C12 C 0.0004(10) 0.0922(13) 0.7921(15) 0.065(3) Uani 1 1 d . . . H12 H -0.0334 0.0704 0.7142 0.078 Uiso 1 1 calc R . . C13 C 0.0807(9) 0.0304(13) 0.8402(14) 0.064(4) Uani 1 1 d . . . H9 H 0.0980 -0.0358 0.7967 0.077 Uiso 1 1 calc R . . C14 C 0.1356(8) 0.0666(10) 0.9529(12) 0.046(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.0507(3) 0.0423(3) 0.0366(3) 0.00613(16) -0.00156(17) -0.00158(17) S1 0.066(2) 0.0606(18) 0.0492(16) -0.0009(14) -0.0043(14) 0.0054(15) Cl1 0.088(2) 0.0495(17) 0.0434(16) -0.0013(12) 0.0073(15) -0.0084(15) O1 0.123(8) 0.056(5) 0.039(4) -0.001(4) -0.002(5) -0.020(6) O2 0.18(2) 0.16(2) 0.24(3) -0.076(17) 0.037(19) 0.046(15) O3 0.120(14) 0.185(18) 0.18(2) -0.041(14) -0.059(13) -0.039(12) O4 0.147(11) 0.125(10) 0.049(6) -0.002(6) 0.003(6) -0.009(9) O5 0.34(3) 0.090(10) 0.073(9) -0.011(7) 0.055(13) -0.035(13) C1 0.041(6) 0.060(7) 0.046(6) 0.008(5) -0.005(5) -0.001(5) C2 0.057(7) 0.054(7) 0.052(7) 0.003(6) -0.001(6) 0.007(6) C3 0.052(8) 0.105(12) 0.064(9) 0.015(8) 0.004(6) 0.013(8) C4 0.044(7) 0.074(10) 0.093(11) 0.027(8) -0.007(7) -0.007(7) C5 0.058(8) 0.058(8) 0.083(10) 0.013(7) -0.009(7) -0.002(6) C6 0.043(6) 0.047(6) 0.061(7) 0.007(5) -0.017(5) -0.001(5) C7 0.077(9) 0.039(6) 0.081(9) 0.003(6) -0.025(7) 0.000(6) C8 0.066(9) 0.095(11) 0.064(9) -0.022(8) 0.003(7) 0.017(8) C9 0.047(7) 0.074(9) 0.059(7) 0.024(7) 0.006(6) -0.004(6) C10 0.059(8) 0.062(8) 0.092(11) 0.004(8) 0.018(8) 0.015(6) C11 0.034(7) 0.116(13) 0.095(12) 0.062(11) 0.005(7) 0.008(7) C12 0.054(8) 0.072(9) 0.069(9) 0.022(7) -0.005(6) -0.006(7) C13 0.048(7) 0.092(11) 0.054(8) 0.024(7) 0.002(6) -0.013(7) C14 0.045(6) 0.045(6) 0.048(6) 0.010(5) 0.018(5) 0.004(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 Bi C14 2.262(11) . ? Bi C1 2.266(12) . ? Bi O1 2.481(8) . ? Bi S1 2.692(3) . ? S1 C7 1.814(15) . ? S1 C8 1.845(14) . ? Cl1 O2 1.36(2) . ? Cl1 O4 1.410(12) . ? Cl1 O3 1.423(17) . ? Cl1 O5 1.422(16) . ? O1 H1A 0.83(2) . ? O1 H1B 0.83(2) . ? C1 C2 1.344(18) . ? C1 C6 1.400(17) . ? C2 C3 1.37(2) . ? C2 H2 0.9300 . ? C3 C4 1.37(2) . ? C3 H3 0.9300 . ? C4 C5 1.36(2) . ? C4 H4 0.9300 . ? C5 C6 1.405(18) . ? C5 H5 0.9300 . ? C6 C7 1.490(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.52(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.336(18) . ? C9 C10 1.425(18) . ? C10 C11 1.38(2) . ? C10 H10 0.9300 . ? C11 C12 1.37(2) . ? C11 H11 0.9300 . ? C12 C13 1.394(19) . ? C12 H12 0.9300 . ? C13 C14 1.40(2) . ? C13 H9 0.9300 . ? 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 C14 Bi C1 96.8(4) . . ? C14 Bi O1 89.8(4) . . ? C1 Bi O1 86.9(4) . . ? C14 Bi S1 77.1(3) . . ? C1 Bi S1 78.4(3) . . ? O1 Bi S1 158.9(2) . . ? C7 S1 C8 101.1(7) . . ? C7 S1 Bi 94.9(4) . . ? C8 S1 Bi 95.5(5) . . ? O2 Cl1 O4 110.4(14) . . ? O2 Cl1 O3 105.9(16) . . ? O4 Cl1 O3 108.6(11) . . ? O2 Cl1 O5 116.9(16) . . ? O4 Cl1 O5 105.7(8) . . ? O3 Cl1 O5 109.2(15) . . ? Bi O1 H1A 121(9) . . ? Bi O1 H1B 142(9) . . ? H1A O1 H1B 97(3) . . ? C2 C1 C6 120.2(12) . . ? C2 C1 Bi 121.4(10) . . ? C6 C1 Bi 118.2(9) . . ? C1 C2 C3 119.7(14) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 122.4(15) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 118.4(13) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 120.4(14) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.8(12) . . ? C1 C6 C7 122.8(11) . . ? C5 C6 C7 118.2(12) . . ? C6 C7 S1 114.6(9) . . ? C6 C7 H7A 108.6 . . ? S1 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? S1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 S1 112.7(9) . . ? C9 C8 H8A 109.1 . . ? S1 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? S1 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 119.9(13) . . ? C14 C9 C8 123.9(12) . . ? C10 C9 C8 116.1(13) . . ? C11 C10 C9 119.5(14) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 120.5(13) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 118.8(14) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 C14 120.9(14) . . ? C12 C13 H9 119.5 . . ? C14 C13 H9 119.5 . . ? C9 C14 C13 119.9(12) . . ? C9 C14 Bi 120.6(9) . . ? C13 C14 Bi 119.3(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 Bi S1 C7 -78.8(5) . . . . ? C1 Bi S1 C7 21.1(5) . . . . ? O1 Bi S1 C7 -25.9(9) . . . . ? C14 Bi S1 C8 22.9(6) . . . . ? C1 Bi S1 C8 122.7(6) . . . . ? O1 Bi S1 C8 75.7(10) . . . . ? C14 Bi C1 C2 -119.5(10) . . . . ? O1 Bi C1 C2 -30.0(10) . . . . ? S1 Bi C1 C2 165.3(10) . . . . ? C14 Bi C1 C6 65.6(9) . . . . ? O1 Bi C1 C6 155.0(9) . . . . ? S1 Bi C1 C6 -9.7(8) . . . . ? C6 C1 C2 C3 -0.2(18) . . . . ? Bi C1 C2 C3 -175.0(10) . . . . ? C1 C2 C3 C4 2(2) . . . . ? C2 C3 C4 C5 -2(2) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C2 C1 C6 C5 -1.7(17) . . . . ? Bi C1 C6 C5 173.3(9) . . . . ? C2 C1 C6 C7 174.5(12) . . . . ? Bi C1 C6 C7 -10.5(15) . . . . ? C4 C5 C6 C1 1.9(19) . . . . ? C4 C5 C6 C7 -174.5(12) . . . . ? C1 C6 C7 S1 34.6(15) . . . . ? C5 C6 C7 S1 -149.2(10) . . . . ? C8 S1 C7 C6 -130.2(10) . . . . ? Bi S1 C7 C6 -33.6(9) . . . . ? C7 S1 C8 C9 64.4(12) . . . . ? Bi S1 C8 C9 -31.7(12) . . . . ? S1 C8 C9 C14 27.8(18) . . . . ? S1 C8 C9 C10 -153.6(10) . . . . ? C14 C9 C10 C11 7(2) . . . . ? C8 C9 C10 C11 -172.2(13) . . . . ? C9 C10 C11 C12 -5(2) . . . . ? C10 C11 C12 C13 4(2) . . . . ? C11 C12 C13 C14 -3.9(19) . . . . ? C10 C9 C14 C13 -6.8(18) . . . . ? C8 C9 C14 C13 171.9(12) . . . . ? C10 C9 C14 Bi 179.4(9) . . . . ? C8 C9 C14 Bi -2.0(17) . . . . ? C12 C13 C14 C9 5.6(18) . . . . ? C12 C13 C14 Bi 179.5(9) . . . . ? C1 Bi C14 C9 -91.9(10) . . . . ? O1 Bi C14 C9 -178.8(9) . . . . ? S1 Bi C14 C9 -15.5(9) . . . . ? C1 Bi C14 C13 94.2(9) . . . . ? O1 Bi C14 C13 7.3(9) . . . . ? S1 Bi C14 C13 170.7(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O5 0.83(2) 1.89(4) 2.712(17) 169(16) . O1 H1A O4 0.83(2) 1.97(3) 2.801(17) 176(14) 4_556 O1 H1A O5 0.83(2) 2.62(10) 3.182(17) 126(10) 4_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.871 _refine_diff_density_min -2.336 _refine_diff_density_rms 0.266