Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _audit_creation_method SHELXL-97 _journal_coden_Cambridge 222 # SUBMISSION DETAILS _publ_contact_author_name 'Dr Nicholas C. Norman' _publ_contact_author_address ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; _publ_contact_author_email n.c.norman@bris.ac.uk _publ_contact_author_fax '+44(0)117 929 0509' _publ_contact_author_phone '+44(0)117 928 7577' _publ_contact_letter ; Date: 13/1/3 Please consider this CIF submission for publication in Dalton Transactions. ; _publ_requested_journal 'Dalton Trans.' # TITLE AND AUTHOR LIST _publ_section_title ; Coordination Complexes of the Bismuth(III) Thiolates Bi(SC~6~F~5~)~3~ and Bi(SC~6~Cl~5~)~3~ with Pyridine Ligands. ; loop_ _publ_author_name _publ_author_address 'Kirsty M. Anderson' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Christian J. Baylies' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'A. H. M. Monowar Jahan' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Nicholas C. Norman' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'A. Guy Orpen' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Jonathan Starbuck' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; _publ_section_references ; Bruker (1998). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison WI, USA. Sheldrick, G. M. (1996). SADABS: A program for absorption correction with the Siemens SMART system; University of Gottingen: Germany. ; ######################################################################### data_3 _database_code_CSD 211633 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H7 Bi C115 N O S3, C3 H7 N O' _chemical_formula_sum 'C24 H14 Bi Cl15 N2 O2 S3' _chemical_formula_weight 1199.28 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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 _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5990(13) _cell_length_b 14.627(2) _cell_length_c 26.667(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.179(3) _cell_angle_gamma 90.00 _cell_volume 3715.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 963 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.74 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2296 _exptl_absorpt_coefficient_mu 6.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.735 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23718 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.1125 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8509 _reflns_number_gt 5047 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.0406P)^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 8509 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 1.56977(3) 0.62758(2) 0.683891(11) 0.02624(9) Uani 1 1 d . . . S3 S 1.7016(2) 0.50106(15) 0.73815(7) 0.0334(5) Uani 1 1 d . . . S2 S 1.8193(2) 0.70521(15) 0.69307(7) 0.0323(5) Uani 1 1 d . . . S1 S 1.6209(2) 0.52924(15) 0.60424(7) 0.0353(5) Uani 1 1 d . . . C1 C 1.5897(9) 0.7626(6) 0.7943(3) 0.038(2) Uani 1 1 d . . . H1A H 1.6710 0.7864 0.7838 0.045 Uiso 1 1 calc R . . C2 C 1.6435(12) 0.8517(6) 0.8702(4) 0.071(4) Uani 1 1 d . . . H2A H 1.7196 0.8730 0.8532 0.106 Uiso 1 1 calc R . . H2B H 1.6804 0.8210 0.9009 0.106 Uiso 1 1 calc R . . H2C H 1.5874 0.9028 0.8782 0.106 Uiso 1 1 calc R . . C3 C 1.4358(11) 0.7509(7) 0.8566(3) 0.063(3) Uani 1 1 d . . . H3A H 1.3886 0.7112 0.8312 0.094 Uiso 1 1 calc R . . H3B H 1.3735 0.7992 0.8637 0.094 Uiso 1 1 calc R . . H3C H 1.4639 0.7166 0.8868 0.094 Uiso 1 1 calc R . . C4 C 1.2670(9) 0.5846(6) 0.7388(3) 0.037(2) Uani 1 1 d . . . H4A H 1.3177 0.6239 0.7617 0.044 Uiso 1 1 calc R . . C5 C 1.0877(10) 0.5810(6) 0.7956(3) 0.050(2) Uani 1 1 d . . . H5A H 1.1509 0.6225 0.8148 0.075 Uiso 1 1 calc R . . H5B H 1.0741 0.5281 0.8157 0.075 Uiso 1 1 calc R . . H5C H 0.9991 0.6107 0.7862 0.075 Uiso 1 1 calc R . . C6 C 1.0655(10) 0.4897(6) 0.7163(4) 0.055(3) Uani 1 1 d . . . H6A H 1.1161 0.4772 0.6882 0.082 Uiso 1 1 calc R . . H6B H 0.9761 0.5162 0.7042 0.082 Uiso 1 1 calc R . . H6C H 1.0514 0.4338 0.7338 0.082 Uiso 1 1 calc R . . C11 C 1.5872(8) 0.4747(5) 0.7828(3) 0.0245(17) Uani 1 1 d . . . C12 C 1.4788(8) 0.4109(5) 0.7724(3) 0.0258(18) Uani 1 1 d . . . C13 C 1.3912(7) 0.3876(5) 0.8089(3) 0.0293(19) Uani 1 1 d . . . C14 C 1.4126(8) 0.4269(6) 0.8565(3) 0.0325(19) Uani 1 1 d . . . C15 C 1.5212(9) 0.4882(5) 0.8688(3) 0.0316(19) Uani 1 1 d . . . C16 C 1.6091(8) 0.5115(5) 0.8327(3) 0.0276(18) Uani 1 1 d . . . C21 C 1.7989(8) 0.7585(5) 0.6328(3) 0.0296(19) Uani 1 1 d . . . C22 C 1.6952(9) 0.8247(6) 0.6195(3) 0.033(2) Uani 1 1 d . . . C23 C 1.6762(9) 0.8657(6) 0.5721(3) 0.037(2) Uani 1 1 d . . . C24 C 1.7639(10) 0.8389(6) 0.5365(3) 0.046(2) Uani 1 1 d . . . C25 C 1.8685(10) 0.7751(7) 0.5493(3) 0.045(2) Uani 1 1 d . . . C26 C 1.8854(9) 0.7341(6) 0.5965(3) 0.038(2) Uani 1 1 d . . . C31 C 1.5914(8) 0.5910(5) 0.5475(3) 0.0272(18) Uani 1 1 d . . . C32 C 1.6715(8) 0.5693(6) 0.5087(3) 0.0317(19) Uani 1 1 d . . . C33 C 1.6478(9) 0.6115(6) 0.4618(3) 0.038(2) Uani 1 1 d . . . C34 C 1.5486(9) 0.6813(6) 0.4531(3) 0.036(2) Uani 1 1 d . . . C35 C 1.4668(9) 0.7041(6) 0.4894(3) 0.035(2) Uani 1 1 d . . . C36 C 1.4883(8) 0.6582(5) 0.5365(3) 0.0267(18) Uani 1 1 d . . . N1 N 1.5588(8) 0.7897(5) 0.8382(2) 0.0423(19) Uani 1 1 d . . . N2 N 1.1461(7) 0.5536(5) 0.7508(3) 0.0391(18) Uani 1 1 d . . . O1 O 1.5222(6) 0.7088(4) 0.76579(19) 0.0374(14) Uani 1 1 d . . . O2 O 1.3181(6) 0.5664(4) 0.7004(2) 0.0439(15) Uani 1 1 d . . . Cl12 Cl 1.4510(2) 0.36095(15) 0.71386(7) 0.0407(5) Uani 1 1 d . . . Cl13 Cl 1.2543(2) 0.31228(16) 0.79363(9) 0.0513(6) Uani 1 1 d . . . Cl14 Cl 1.3028(2) 0.40051(16) 0.90048(8) 0.0492(6) Uani 1 1 d . . . Cl15 Cl 1.5501(2) 0.53565(16) 0.92792(7) 0.0431(6) Uani 1 1 d . . . Cl16 Cl 1.7462(2) 0.58603(15) 0.84878(8) 0.0382(5) Uani 1 1 d . . . Cl22 Cl 1.5870(2) 0.85870(14) 0.66372(8) 0.0391(5) Uani 1 1 d . . . Cl23 Cl 1.5495(3) 0.94667(18) 0.55755(9) 0.0565(7) Uani 1 1 d . . . Cl24 Cl 1.7408(3) 0.8884(2) 0.47779(8) 0.0726(9) Uani 1 1 d . . . Cl25 Cl 1.9758(3) 0.7437(2) 0.50532(9) 0.0718(9) Uani 1 1 d . . . Cl26 Cl 2.0180(3) 0.65629(17) 0.61141(10) 0.0564(7) Uani 1 1 d . . . Cl32 Cl 1.7999(2) 0.48674(17) 0.51845(8) 0.0475(6) Uani 1 1 d . . . Cl33 Cl 1.7442(3) 0.57749(18) 0.41398(8) 0.0556(7) Uani 1 1 d . . . Cl34 Cl 1.5232(3) 0.73471(18) 0.39476(8) 0.0606(7) Uani 1 1 d . . . Cl35 Cl 1.3404(3) 0.78605(17) 0.47831(8) 0.0546(7) Uani 1 1 d . . . Cl36 Cl 1.3771(2) 0.68642(16) 0.58037(7) 0.0420(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02749(15) 0.03057(16) 0.02198(14) 0.00176(16) 0.00832(10) -0.00310(15) S3 0.0311(11) 0.0414(13) 0.0297(11) 0.0093(10) 0.0120(9) 0.0059(9) S2 0.0292(11) 0.0402(13) 0.0278(11) 0.0042(10) 0.0040(9) -0.0064(9) S1 0.0492(14) 0.0338(13) 0.0239(10) -0.0011(9) 0.0085(9) 0.0029(10) C1 0.039(5) 0.031(5) 0.043(5) -0.002(4) 0.005(4) -0.001(4) C2 0.097(9) 0.047(7) 0.057(7) -0.019(5) -0.038(6) 0.003(6) C3 0.087(9) 0.064(8) 0.042(6) -0.002(5) 0.027(6) 0.013(6) C4 0.038(5) 0.026(5) 0.046(5) 0.003(4) 0.003(4) -0.008(4) C5 0.052(6) 0.053(6) 0.048(6) -0.001(5) 0.017(5) 0.001(5) C6 0.047(6) 0.049(6) 0.068(7) -0.013(5) 0.009(5) -0.016(5) C11 0.029(4) 0.018(4) 0.029(4) 0.007(3) 0.011(3) 0.004(3) C12 0.039(5) 0.021(4) 0.016(4) -0.004(3) 0.000(3) 0.007(3) C13 0.025(4) 0.024(5) 0.039(5) 0.003(4) 0.007(4) 0.002(3) C14 0.034(5) 0.034(5) 0.031(5) 0.003(4) 0.013(4) 0.003(4) C15 0.047(5) 0.026(5) 0.025(4) 0.008(4) 0.017(4) 0.011(4) C16 0.032(4) 0.023(4) 0.029(4) 0.003(4) 0.006(3) 0.007(3) C21 0.034(5) 0.034(5) 0.021(4) -0.001(4) 0.007(3) -0.015(4) C22 0.042(5) 0.035(5) 0.024(4) -0.005(4) 0.008(4) -0.013(4) C23 0.044(5) 0.037(5) 0.027(4) 0.005(4) -0.007(4) -0.017(4) C24 0.057(6) 0.054(6) 0.026(5) 0.006(4) 0.009(4) -0.031(5) C25 0.044(6) 0.069(7) 0.024(5) 0.001(5) 0.015(4) -0.024(5) C26 0.036(5) 0.040(6) 0.039(5) -0.005(4) 0.010(4) -0.011(4) C31 0.030(4) 0.025(4) 0.027(4) 0.002(4) 0.004(3) -0.006(3) C32 0.032(5) 0.035(5) 0.029(4) 0.001(4) 0.009(4) -0.003(4) C33 0.044(5) 0.049(6) 0.025(4) -0.007(4) 0.016(4) -0.015(4) C34 0.056(6) 0.031(5) 0.022(4) 0.001(4) 0.007(4) -0.009(4) C35 0.042(5) 0.036(5) 0.026(4) -0.005(4) 0.004(4) -0.001(4) C36 0.031(4) 0.030(5) 0.021(4) -0.002(3) 0.008(3) -0.006(3) N1 0.068(6) 0.030(4) 0.027(4) -0.010(3) -0.001(4) 0.009(4) N2 0.028(4) 0.043(5) 0.050(5) 0.006(4) 0.016(3) -0.003(3) O1 0.037(3) 0.045(4) 0.033(3) -0.007(3) 0.012(3) -0.005(3) O2 0.040(4) 0.043(4) 0.053(4) -0.005(3) 0.021(3) -0.001(3) Cl12 0.0522(13) 0.0401(13) 0.0295(10) -0.0056(10) 0.0035(9) -0.0006(10) Cl13 0.0466(14) 0.0468(15) 0.0620(15) -0.0015(12) 0.0129(12) -0.0153(11) Cl14 0.0527(14) 0.0528(16) 0.0486(13) 0.0063(11) 0.0328(11) -0.0030(11) Cl15 0.0553(14) 0.0479(14) 0.0279(11) -0.0056(10) 0.0126(10) 0.0057(11) Cl16 0.0360(12) 0.0391(12) 0.0394(12) -0.0029(10) 0.0042(10) -0.0046(9) Cl22 0.0445(12) 0.0373(14) 0.0376(11) 0.0053(10) 0.0133(9) -0.0012(10) Cl23 0.0549(16) 0.0620(17) 0.0490(14) 0.0245(13) -0.0082(12) -0.0093(12) Cl24 0.0801(19) 0.112(3) 0.0245(12) 0.0207(14) 0.0037(12) -0.0437(18) Cl25 0.081(2) 0.100(2) 0.0425(14) -0.0113(15) 0.0391(14) -0.0293(17) Cl26 0.0494(15) 0.0601(17) 0.0657(16) 0.0027(13) 0.0314(13) 0.0016(12) Cl32 0.0465(14) 0.0615(16) 0.0368(12) -0.0005(11) 0.0136(10) 0.0116(11) Cl33 0.0668(17) 0.0713(18) 0.0340(12) -0.0003(12) 0.0269(12) -0.0051(13) Cl34 0.098(2) 0.0572(17) 0.0260(12) 0.0092(11) 0.0051(12) -0.0038(14) Cl35 0.0752(18) 0.0494(15) 0.0355(12) 0.0005(11) -0.0078(12) 0.0186(13) Cl36 0.0420(13) 0.0549(15) 0.0299(11) -0.0022(10) 0.0070(9) 0.0106(11) _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 O1 2.577(5) . ? Bi1 S3 2.581(2) . ? Bi1 S2 2.634(2) . ? Bi1 S1 2.661(2) . ? Bi1 O2 2.664(6) . ? S3 C11 1.761(7) . ? S2 C21 1.776(8) . ? S1 C31 1.755(7) . ? C1 O1 1.223(9) . ? C1 N1 1.305(10) . ? C2 N1 1.428(10) . ? C3 N1 1.448(12) . ? C4 O2 1.218(9) . ? C4 N2 1.323(10) . ? C5 N2 1.438(10) . ? C6 N2 1.463(10) . ? C11 C12 1.399(10) . ? C11 C16 1.427(10) . ? C12 C13 1.406(10) . ? C12 Cl12 1.713(7) . ? C13 C14 1.385(10) . ? C13 Cl13 1.724(8) . ? C14 C15 1.383(11) . ? C14 Cl14 1.716(8) . ? C15 C16 1.398(10) . ? C15 Cl15 1.714(8) . ? C16 Cl16 1.721(8) . ? C21 C26 1.397(11) . ? C21 C22 1.402(11) . ? C22 C23 1.391(10) . ? C22 Cl22 1.739(8) . ? C23 C24 1.400(12) . ? C23 Cl23 1.707(9) . ? C24 C25 1.382(13) . ? C24 Cl24 1.715(8) . ? C25 C26 1.385(11) . ? C25 Cl25 1.719(9) . ? C26 Cl26 1.717(9) . ? C31 C32 1.399(10) . ? C31 C36 1.400(10) . ? C32 C33 1.390(10) . ? C32 Cl32 1.722(8) . ? C33 C34 1.395(12) . ? C33 Cl33 1.739(8) . ? C34 C35 1.362(11) . ? C34 Cl34 1.729(8) . ? C35 C36 1.417(10) . ? C35 Cl35 1.705(9) . ? C36 Cl36 1.729(7) . ? 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 O1 Bi1 S3 88.96(13) . . ? O1 Bi1 S2 88.73(13) . . ? S3 Bi1 S2 83.15(7) . . ? O1 Bi1 S1 174.65(14) . . ? S3 Bi1 S1 86.19(7) . . ? S2 Bi1 S1 92.93(7) . . ? O1 Bi1 O2 75.79(18) . . ? S3 Bi1 O2 93.30(14) . . ? S2 Bi1 O2 164.20(14) . . ? S1 Bi1 O2 102.22(14) . . ? C11 S3 Bi1 103.5(2) . . ? C21 S2 Bi1 96.3(3) . . ? C31 S1 Bi1 112.6(3) . . ? O1 C1 N1 126.3(8) . . ? O2 C4 N2 125.9(8) . . ? C12 C11 C16 117.2(6) . . ? C12 C11 S3 121.5(6) . . ? C16 C11 S3 121.1(6) . . ? C11 C12 C13 121.2(6) . . ? C11 C12 Cl12 119.5(6) . . ? C13 C12 Cl12 119.3(6) . . ? C14 C13 C12 120.1(7) . . ? C14 C13 Cl13 120.2(6) . . ? C12 C13 Cl13 119.7(6) . . ? C15 C14 C13 120.4(7) . . ? C15 C14 Cl14 119.6(6) . . ? C13 C14 Cl14 120.0(6) . . ? C14 C15 C16 119.9(7) . . ? C14 C15 Cl15 120.7(6) . . ? C16 C15 Cl15 119.4(7) . . ? C15 C16 C11 121.2(7) . . ? C15 C16 Cl16 119.5(6) . . ? C11 C16 Cl16 119.3(6) . . ? C26 C21 C22 117.8(7) . . ? C26 C21 S2 120.4(7) . . ? C22 C21 S2 121.7(6) . . ? C23 C22 C21 122.4(8) . . ? C23 C22 Cl22 118.2(7) . . ? C21 C22 Cl22 119.5(6) . . ? C22 C23 C24 118.2(8) . . ? C22 C23 Cl23 120.9(7) . . ? C24 C23 Cl23 120.9(7) . . ? C25 C24 C23 120.1(8) . . ? C25 C24 Cl24 121.2(7) . . ? C23 C24 Cl24 118.7(8) . . ? C24 C25 C26 121.1(8) . . ? C24 C25 Cl25 119.4(7) . . ? C26 C25 Cl25 119.5(8) . . ? C25 C26 C21 120.4(8) . . ? C25 C26 Cl26 119.8(7) . . ? C21 C26 Cl26 119.8(7) . . ? C32 C31 C36 116.4(7) . . ? C32 C31 S1 118.4(6) . . ? C36 C31 S1 125.2(6) . . ? C33 C32 C31 121.4(8) . . ? C33 C32 Cl32 118.7(6) . . ? C31 C32 Cl32 119.8(6) . . ? C32 C33 C34 120.5(7) . . ? C32 C33 Cl33 119.4(7) . . ? C34 C33 Cl33 120.1(6) . . ? C35 C34 C33 120.1(7) . . ? C35 C34 Cl34 120.0(7) . . ? C33 C34 Cl34 119.8(6) . . ? C34 C35 C36 118.8(8) . . ? C34 C35 Cl35 120.6(6) . . ? C36 C35 Cl35 120.5(6) . . ? C31 C36 C35 122.6(7) . . ? C31 C36 Cl36 120.4(6) . . ? C35 C36 Cl36 117.0(6) . . ? C1 N1 C2 123.6(9) . . ? C1 N1 C3 118.0(8) . . ? C2 N1 C3 118.3(8) . . ? C4 N2 C5 123.4(8) . . ? C4 N2 C6 118.5(7) . . ? C5 N2 C6 118.1(7) . . ? C1 O1 Bi1 133.5(5) . . ? C4 O2 Bi1 122.2(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.147 _refine_diff_density_min -0.940 _refine_diff_density_rms 0.173 #===END data_4a _database_code_CSD 211634 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi F15 S3, 3(C5 H5 N)' _chemical_formula_sum 'C33 H15 Bi F15 N3 S3' _chemical_formula_weight 1043.67 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' 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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7632(8) _cell_length_b 13.6101(16) _cell_length_c 30.018(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.040(15) _cell_angle_gamma 90.00 _cell_volume 3566.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 225 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.944 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 5.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.191 _exptl_absorpt_correction_T_max 0.350 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 22813 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0866 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.57 _reflns_number_total 8195 _reflns_number_gt 5118 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0185P)^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 8195 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 0.898 _refine_ls_restrained_S_all 0.898 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.30187(2) 0.636007(13) 0.151525(6) 0.03471(6) Uani 1 1 d . . . S1 S 0.20470(14) 0.52784(9) 0.21567(4) 0.0375(3) Uani 1 1 d . . . C11 C 0.3466(5) 0.5496(3) 0.25980(15) 0.0354(12) Uani 1 1 d . . . F12 F 0.5216(3) 0.4400(2) 0.23090(9) 0.0518(8) Uani 1 1 d . . . C12 C 0.4881(6) 0.5032(4) 0.26311(16) 0.0385(12) Uani 1 1 d . . . F13 F 0.7342(3) 0.4754(2) 0.29884(10) 0.0660(9) Uani 1 1 d . . . C13 C 0.5984(6) 0.5211(4) 0.29737(18) 0.0447(13) Uani 1 1 d . . . F14 F 0.6788(3) 0.6069(2) 0.36365(10) 0.0655(10) Uani 1 1 d . . . C14 C 0.5714(6) 0.5884(4) 0.33006(17) 0.0450(13) Uani 1 1 d . . . F15 F 0.4031(3) 0.7007(2) 0.35992(10) 0.0585(8) Uani 1 1 d . . . C15 C 0.4322(6) 0.6347(4) 0.32803(16) 0.0417(12) Uani 1 1 d . . . F16 F 0.1892(3) 0.6645(2) 0.29342(9) 0.0491(8) Uani 1 1 d . . . C16 C 0.3233(5) 0.6157(3) 0.29383(15) 0.0350(12) Uani 1 1 d . . . S2 S 0.15830(14) 0.78577(9) 0.18490(4) 0.0399(3) Uani 1 1 d . . . C21 C 0.1734(5) 0.8756(3) 0.14350(15) 0.0368(12) Uani 1 1 d . . . F22 F 0.4315(3) 0.9129(2) 0.16772(9) 0.0498(8) Uani 1 1 d . . . C22 C 0.3066(6) 0.9302(3) 0.13999(16) 0.0377(12) Uani 1 1 d . . . F23 F 0.4490(4) 1.0495(2) 0.10433(10) 0.0622(9) Uani 1 1 d . . . C23 C 0.3164(6) 1.0006(4) 0.10721(18) 0.0443(14) Uani 1 1 d . . . F24 F 0.2034(4) 1.0894(2) 0.04603(10) 0.0698(10) Uani 1 1 d . . . C24 C 0.1931(7) 1.0210(4) 0.07800(18) 0.0476(14) Uani 1 1 d . . . C25 C 0.0601(6) 0.9700(4) 0.08079(18) 0.0484(14) Uani 1 1 d . . . F25 F -0.0622(4) 0.9902(2) 0.05151(11) 0.0706(10) Uani 1 1 d . . . F26 F -0.0822(3) 0.8518(2) 0.11430(10) 0.0610(9) Uani 1 1 d . . . C26 C 0.0509(6) 0.8992(4) 0.11292(17) 0.0429(13) Uani 1 1 d . . . S3 S 0.03414(15) 0.59796(11) 0.10759(5) 0.0504(4) Uani 1 1 d . . . C31 C 0.0627(6) 0.4910(4) 0.07555(17) 0.0415(13) Uani 1 1 d . . . C32 C 0.1521(6) 0.4884(4) 0.04060(17) 0.0403(13) Uani 1 1 d . . . F32 F 0.2322(3) 0.5698(2) 0.03065(9) 0.0529(8) Uani 1 1 d . . . F33 F 0.2567(3) 0.4105(2) -0.01994(10) 0.0585(8) Uani 1 1 d . . . C33 C 0.1663(6) 0.4087(4) 0.01363(17) 0.0431(13) Uani 1 1 d . . . C34 C 0.0819(6) 0.3252(4) 0.02120(18) 0.0439(14) Uani 1 1 d . . . F34 F 0.0898(3) 0.2462(2) -0.00559(10) 0.0558(8) Uani 1 1 d . . . F35 F -0.0914(3) 0.2429(2) 0.06326(10) 0.0619(9) Uani 1 1 d . . . C35 C -0.0081(6) 0.3238(4) 0.05599(19) 0.0458(14) Uani 1 1 d . . . F36 F -0.1038(3) 0.3988(2) 0.11732(11) 0.0637(9) Uani 1 1 d . . . C36 C -0.0166(6) 0.4040(4) 0.08301(17) 0.0445(14) Uani 1 1 d . . . N101 N 0.5574(5) 0.6946(3) 0.20478(15) 0.0475(11) Uani 1 1 d . . . C101 C 0.5610(6) 0.7606(4) 0.23739(19) 0.0507(15) Uani 1 1 d . . . H10A H 0.4697 0.7955 0.2418 0.061 Uiso 1 1 calc R . . C102 C 0.6894(7) 0.7806(4) 0.2649(2) 0.0671(19) Uani 1 1 d . . . H10B H 0.6875 0.8285 0.2879 0.081 Uiso 1 1 calc R . . C103 C 0.8221(7) 0.7301(5) 0.2586(3) 0.077(2) Uani 1 1 d . . . H10C H 0.9134 0.7428 0.2772 0.092 Uiso 1 1 calc R . . C104 C 0.8209(7) 0.6622(5) 0.2256(3) 0.078(2) Uani 1 1 d . . . H10D H 0.9109 0.6261 0.2210 0.094 Uiso 1 1 calc R . . C105 C 0.6875(6) 0.6461(4) 0.1988(2) 0.0631(17) Uani 1 1 d . . . H10E H 0.6875 0.5993 0.1753 0.076 Uiso 1 1 calc R . . N201 N 0.4186(5) 0.4632(3) 0.11886(14) 0.0429(11) Uani 1 1 d . . . C201 C 0.5089(6) 0.4666(4) 0.08552(19) 0.0482(14) Uani 1 1 d . . . H20A H 0.5336 0.5291 0.0741 0.058 Uiso 1 1 calc R . . C202 C 0.5681(6) 0.3850(4) 0.06673(18) 0.0524(15) Uani 1 1 d . . . H20B H 0.6295 0.3906 0.0423 0.063 Uiso 1 1 calc R . . C203 C 0.5362(7) 0.2945(4) 0.0842(2) 0.0620(17) Uani 1 1 d . . . H20C H 0.5770 0.2363 0.0724 0.074 Uiso 1 1 calc R . . C204 C 0.4453(6) 0.2895(4) 0.11868(19) 0.0549(16) Uani 1 1 d . . . H20D H 0.4220 0.2281 0.1315 0.066 Uiso 1 1 calc R . . C205 C 0.3882(6) 0.3759(4) 0.13440(16) 0.0440(13) Uani 1 1 d . . . H20E H 0.3227 0.3720 0.1579 0.053 Uiso 1 1 calc R . . N301 N 0.3974(5) 0.7517(3) 0.08017(14) 0.0440(11) Uani 1 1 d . . . C301 C 0.2993(6) 0.7831(4) 0.04692(17) 0.0417(13) Uani 1 1 d . . . H30A H 0.1954 0.7629 0.0465 0.050 Uiso 1 1 calc R . . C302 C 0.3400(7) 0.8433(4) 0.01302(17) 0.0488(14) Uani 1 1 d . . . H30B H 0.2658 0.8649 -0.0098 0.059 Uiso 1 1 calc R . . C303 C 0.4901(7) 0.8710(4) 0.01312(18) 0.0596(16) Uani 1 1 d . . . H30C H 0.5221 0.9124 -0.0098 0.071 Uiso 1 1 calc R . . C304 C 0.5933(7) 0.8384(4) 0.0466(2) 0.0628(17) Uani 1 1 d . . . H30D H 0.6982 0.8564 0.0473 0.075 Uiso 1 1 calc R . . C305 C 0.5430(6) 0.7790(4) 0.07959(19) 0.0521(15) Uani 1 1 d . . . H30E H 0.6153 0.7567 0.1028 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.04216(10) 0.03080(10) 0.03117(10) 0.00216(11) 0.00327(7) 0.00195(11) S1 0.0418(7) 0.0377(8) 0.0331(7) 0.0011(6) 0.0037(6) 0.0009(6) C11 0.045(3) 0.031(3) 0.031(3) 0.007(2) 0.010(2) 0.003(2) F12 0.0562(19) 0.056(2) 0.0436(19) -0.0062(15) 0.0072(15) 0.0223(15) C12 0.048(3) 0.036(3) 0.033(3) 0.000(2) 0.013(3) 0.005(3) F13 0.049(2) 0.084(3) 0.064(2) 0.0023(18) -0.0001(17) 0.0255(18) C13 0.036(3) 0.050(4) 0.048(4) 0.008(3) 0.006(3) 0.009(3) F14 0.058(2) 0.080(3) 0.055(2) -0.0078(17) -0.0153(17) 0.0029(17) C14 0.051(4) 0.048(4) 0.035(3) 0.004(3) -0.001(3) -0.003(3) F15 0.070(2) 0.054(2) 0.051(2) -0.0199(16) 0.0012(17) 0.0011(16) C15 0.049(3) 0.036(3) 0.041(3) -0.003(3) 0.011(2) 0.000(3) F16 0.0456(17) 0.055(2) 0.0466(18) -0.0099(14) 0.0057(14) 0.0127(14) C16 0.038(3) 0.036(3) 0.032(3) 0.006(2) 0.007(2) 0.005(2) S2 0.0459(8) 0.0333(8) 0.0415(8) 0.0029(6) 0.0096(6) 0.0045(6) C21 0.045(3) 0.032(3) 0.034(3) 0.001(2) 0.006(2) 0.011(3) F22 0.0446(18) 0.0458(19) 0.058(2) 0.0071(15) -0.0021(16) -0.0054(14) C22 0.045(3) 0.027(3) 0.041(3) 0.000(2) 0.006(3) 0.006(2) F23 0.072(2) 0.044(2) 0.074(2) 0.0054(16) 0.0246(18) -0.0135(17) C23 0.055(4) 0.027(3) 0.054(4) -0.005(3) 0.021(3) -0.002(3) F24 0.102(3) 0.053(2) 0.057(2) 0.0237(17) 0.0214(19) 0.0163(19) C24 0.071(4) 0.034(3) 0.040(3) 0.010(3) 0.015(3) 0.013(3) C25 0.048(4) 0.056(4) 0.041(3) 0.005(3) 0.001(3) 0.018(3) F25 0.069(2) 0.083(3) 0.058(2) 0.0186(18) -0.0060(18) 0.0249(19) F26 0.0404(17) 0.074(2) 0.068(2) 0.0124(18) 0.0012(16) 0.0071(17) C26 0.036(3) 0.043(3) 0.050(4) 0.003(3) 0.008(3) 0.009(2) S3 0.0497(9) 0.0525(9) 0.0470(9) -0.0069(7) -0.0064(7) 0.0054(7) C31 0.044(3) 0.042(3) 0.036(3) 0.000(2) -0.012(3) 0.004(3) C32 0.040(3) 0.037(3) 0.042(3) 0.005(3) -0.012(3) 0.001(3) F32 0.064(2) 0.041(2) 0.053(2) 0.0036(15) 0.0027(16) -0.0087(16) F33 0.066(2) 0.063(2) 0.046(2) -0.0054(16) 0.0053(17) 0.0040(16) C33 0.049(3) 0.046(4) 0.034(3) 0.003(3) -0.001(3) 0.003(3) C34 0.050(3) 0.039(3) 0.039(3) -0.003(3) -0.015(3) 0.004(3) F34 0.072(2) 0.0362(19) 0.056(2) -0.0071(15) -0.0147(17) 0.0056(15) F35 0.064(2) 0.052(2) 0.065(2) 0.0086(16) -0.0143(17) -0.0179(17) C35 0.045(3) 0.037(3) 0.050(4) 0.008(3) -0.019(3) -0.007(3) F36 0.059(2) 0.075(2) 0.057(2) 0.0026(17) 0.0020(17) -0.0120(17) C36 0.036(3) 0.061(4) 0.034(3) 0.007(3) -0.008(3) -0.002(3) N101 0.036(3) 0.052(3) 0.055(3) 0.009(2) 0.005(2) 0.002(2) C101 0.048(4) 0.043(4) 0.061(4) 0.020(3) 0.003(3) -0.009(3) C102 0.055(4) 0.058(4) 0.085(5) 0.017(3) -0.015(4) -0.024(3) C103 0.043(4) 0.075(6) 0.109(7) 0.035(4) -0.015(4) -0.016(4) C104 0.035(4) 0.079(6) 0.124(7) 0.038(5) 0.020(4) 0.004(3) C105 0.045(4) 0.070(5) 0.077(4) 0.017(4) 0.020(3) -0.003(3) N201 0.045(3) 0.042(3) 0.042(3) 0.005(2) 0.009(2) 0.005(2) C201 0.042(3) 0.049(4) 0.054(4) 0.008(3) 0.004(3) -0.003(3) C202 0.044(3) 0.065(5) 0.050(4) -0.001(3) 0.013(3) 0.008(3) C203 0.077(4) 0.046(4) 0.068(4) -0.020(3) 0.029(4) 0.000(3) C204 0.074(4) 0.033(4) 0.061(4) -0.011(3) 0.024(3) -0.005(3) C205 0.049(3) 0.042(4) 0.041(3) -0.006(3) 0.009(2) 0.000(3) N301 0.056(3) 0.039(3) 0.037(3) -0.001(2) 0.003(2) 0.001(2) C301 0.040(3) 0.040(3) 0.045(3) -0.010(3) 0.004(3) -0.006(2) C302 0.065(4) 0.040(4) 0.040(3) -0.008(3) -0.003(3) -0.007(3) C303 0.091(5) 0.049(4) 0.041(3) 0.005(3) 0.020(3) -0.009(4) C304 0.058(4) 0.064(5) 0.068(5) -0.005(3) 0.015(4) -0.011(3) C305 0.041(3) 0.064(4) 0.051(4) 0.002(3) -0.003(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 S1 2.6244(13) . ? Bi1 S2 2.6388(13) . ? Bi1 S3 2.6398(14) . ? Bi1 N101 2.753(4) . ? Bi1 N201 2.778(4) . ? S1 C11 1.760(5) . ? C11 C12 1.387(6) . ? C11 C16 1.390(6) . ? F12 C12 1.346(5) . ? C12 C13 1.370(7) . ? F13 C13 1.341(5) . ? C13 C14 1.377(7) . ? F14 C14 1.341(5) . ? C14 C15 1.370(7) . ? F15 C15 1.353(5) . ? C15 C16 1.364(6) . ? F16 C16 1.349(5) . ? S2 C21 1.756(5) . ? C21 C26 1.388(6) . ? C21 C22 1.396(6) . ? F22 C22 1.337(5) . ? C22 C23 1.381(7) . ? F23 C23 1.349(5) . ? C23 C24 1.359(7) . ? F24 C24 1.346(5) . ? C24 C25 1.365(7) . ? C25 F25 1.353(5) . ? C25 C26 1.371(7) . ? F26 C26 1.336(5) . ? S3 C31 1.774(5) . ? C31 C32 1.364(7) . ? C31 C36 1.401(7) . ? C32 F32 1.358(5) . ? C32 C33 1.367(7) . ? F33 C33 1.335(6) . ? C33 C34 1.386(7) . ? C34 F34 1.347(5) . ? C34 C35 1.363(7) . ? F35 C35 1.350(5) . ? C35 C36 1.365(7) . ? F36 C36 1.337(6) . ? N101 C101 1.326(7) . ? N101 C105 1.343(6) . ? C101 C102 1.363(7) . ? C102 C103 1.378(8) . ? C103 C104 1.355(9) . ? C104 C105 1.377(8) . ? N201 C205 1.313(6) . ? N201 C201 1.330(6) . ? C201 C202 1.368(7) . ? C202 C203 1.377(7) . ? C203 C204 1.362(7) . ? C204 C205 1.377(7) . ? N301 C301 1.329(6) . ? N301 C305 1.330(6) . ? C301 C302 1.377(7) . ? C302 C303 1.368(7) . ? C303 C304 1.367(7) . ? C304 C305 1.379(7) . ? 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 S1 Bi1 S2 87.62(4) . . ? S1 Bi1 S3 85.71(4) . . ? S2 Bi1 S3 84.76(4) . . ? S1 Bi1 N101 92.08(9) . . ? S2 Bi1 N101 86.92(10) . . ? S3 Bi1 N101 171.47(10) . . ? S1 Bi1 N201 86.41(9) . . ? S2 Bi1 N201 172.20(9) . . ? S3 Bi1 N201 89.79(9) . . ? N101 Bi1 N201 98.31(13) . . ? C11 S1 Bi1 101.79(16) . . ? C12 C11 C16 115.5(4) . . ? C12 C11 S1 123.0(4) . . ? C16 C11 S1 121.5(4) . . ? F12 C12 C13 118.0(4) . . ? F12 C12 C11 119.3(4) . . ? C13 C12 C11 122.7(5) . . ? F13 C13 C12 120.5(5) . . ? F13 C13 C14 119.5(5) . . ? C12 C13 C14 119.9(5) . . ? F14 C14 C15 120.7(5) . . ? F14 C14 C13 120.5(5) . . ? C15 C14 C13 118.8(5) . . ? F15 C15 C16 119.7(4) . . ? F15 C15 C14 119.8(4) . . ? C16 C15 C14 120.5(5) . . ? F16 C16 C15 117.7(4) . . ? F16 C16 C11 119.7(4) . . ? C15 C16 C11 122.5(5) . . ? C21 S2 Bi1 101.58(16) . . ? C26 C21 C22 115.5(4) . . ? C26 C21 S2 121.8(4) . . ? C22 C21 S2 122.6(4) . . ? F22 C22 C23 117.9(5) . . ? F22 C22 C21 120.2(4) . . ? C23 C22 C21 121.8(5) . . ? F23 C23 C24 119.9(5) . . ? F23 C23 C22 119.7(5) . . ? C24 C23 C22 120.4(5) . . ? F24 C24 C23 120.2(5) . . ? F24 C24 C25 120.4(5) . . ? C23 C24 C25 119.4(5) . . ? F25 C25 C24 119.3(5) . . ? F25 C25 C26 120.5(5) . . ? C24 C25 C26 120.2(5) . . ? F26 C26 C25 117.8(5) . . ? F26 C26 C21 119.6(5) . . ? C25 C26 C21 122.6(5) . . ? C31 S3 Bi1 105.69(16) . . ? C32 C31 C36 115.3(5) . . ? C32 C31 S3 123.8(4) . . ? C36 C31 S3 120.8(4) . . ? F32 C32 C31 119.4(5) . . ? F32 C32 C33 116.2(5) . . ? C31 C32 C33 124.4(5) . . ? F33 C33 C32 121.6(5) . . ? F33 C33 C34 120.0(5) . . ? C32 C33 C34 118.5(5) . . ? F34 C34 C35 120.7(5) . . ? F34 C34 C33 120.0(5) . . ? C35 C34 C33 119.3(5) . . ? F35 C35 C34 119.5(5) . . ? F35 C35 C36 119.8(6) . . ? C34 C35 C36 120.6(5) . . ? F36 C36 C35 118.7(5) . . ? F36 C36 C31 119.5(5) . . ? C35 C36 C31 121.8(5) . . ? C101 N101 C105 117.8(5) . . ? C101 N101 Bi1 126.2(4) . . ? C105 N101 Bi1 115.9(4) . . ? N101 C101 C102 123.2(6) . . ? C101 C102 C103 118.7(7) . . ? C104 C103 C102 119.2(6) . . ? C103 C104 C105 119.2(6) . . ? N101 C105 C104 122.1(6) . . ? C205 N201 C201 116.8(5) . . ? C205 N201 Bi1 123.3(3) . . ? C201 N201 Bi1 119.9(3) . . ? N201 C201 C202 123.7(5) . . ? C201 C202 C203 118.2(5) . . ? C204 C203 C202 119.1(5) . . ? C203 C204 C205 118.2(5) . . ? N201 C205 C204 124.0(5) . . ? C301 N301 C305 117.3(4) . . ? N301 C301 C302 123.6(5) . . ? C303 C302 C301 118.3(5) . . ? C304 C303 C302 119.1(5) . . ? C303 C304 C305 119.1(6) . . ? N301 C305 C304 122.7(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.754 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.110 #===END data_4b _database_code_CSD 211635 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi F15 S3, 3(C5 H5 N)' _chemical_formula_sum 'C33 H15 Bi F15 N3 S3' _chemical_formula_weight 1043.64 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' 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 _symmetry_space_group_name_Hall '-P 2ybc' 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 10.0822(6) _cell_length_b 20.558(2) _cell_length_c 17.130(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.476(10) _cell_angle_gamma 90.00 _cell_volume 3520.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 389 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 5.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.198 _exptl_absorpt_correction_T_max 0.344 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 22387 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.51 _reflns_number_total 8045 _reflns_number_gt 6176 _reflns_threshold_expression >2\s(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^)+(0.0236P)^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 8045 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0527 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 1.208866(12) -0.180806(6) 0.864637(8) 0.02429(4) Uani 1 1 d . . . S1 S 1.23579(9) -0.29572(4) 0.92690(6) 0.0347(2) Uani 1 1 d . . . C11 C 1.4075(3) -0.31550(16) 0.9391(2) 0.0288(7) Uani 1 1 d . . . C12 C 1.4568(3) -0.35964(16) 0.8880(2) 0.0311(8) Uani 1 1 d . . . F12 F 1.3776(2) -0.38438(10) 0.82617(13) 0.0471(6) Uani 1 1 d . . . C13 C 1.5879(4) -0.38120(17) 0.9005(2) 0.0367(9) Uani 1 1 d . . . F13 F 1.6324(2) -0.42447(11) 0.85102(14) 0.0528(6) Uani 1 1 d . . . C14 C 1.6727(3) -0.35819(18) 0.9628(2) 0.0366(9) Uani 1 1 d . . . F14 F 1.8012(2) -0.37779(12) 0.97369(16) 0.0594(7) Uani 1 1 d . . . C15 C 1.6273(3) -0.31414(18) 1.0136(2) 0.0369(9) Uani 1 1 d . . . F15 F 1.7109(2) -0.29189(11) 1.07525(15) 0.0558(7) Uani 1 1 d . . . C16 C 1.4969(4) -0.29360(16) 1.0014(2) 0.0304(8) Uani 1 1 d . . . F16 F 1.4551(2) -0.25313(9) 1.05444(12) 0.0402(5) Uani 1 1 d . . . S2 S 1.32669(10) -0.22790(4) 0.74751(6) 0.0358(2) Uani 1 1 d . . . C21 C 1.3146(3) -0.16247(15) 0.6806(2) 0.0281(8) Uani 1 1 d . . . C22 C 1.1966(3) -0.14865(17) 0.6317(2) 0.0316(8) Uani 1 1 d . . . F22 F 1.0859(2) -0.18346(10) 0.63766(14) 0.0472(6) Uani 1 1 d . . . C23 C 1.1882(3) -0.10068(17) 0.5753(2) 0.0340(8) Uani 1 1 d . . . F23 F 1.0725(2) -0.08872(11) 0.52951(14) 0.0507(6) Uani 1 1 d . . . C24 C 1.3003(4) -0.06426(17) 0.5659(2) 0.0355(9) Uani 1 1 d . . . F24 F 1.2930(2) -0.01799(10) 0.51039(13) 0.0518(6) Uani 1 1 d . . . C25 C 1.4176(3) -0.07648(17) 0.6135(2) 0.0334(8) Uani 1 1 d . . . F25 F 1.5270(2) -0.04153(11) 0.60320(14) 0.0509(6) Uani 1 1 d . . . C26 C 1.4244(3) -0.12440(17) 0.6693(2) 0.0311(8) Uani 1 1 d . . . F26 F 1.54306(19) -0.13522(10) 0.71261(14) 0.0433(5) Uani 1 1 d . . . S3 S 1.45354(8) -0.13676(4) 0.90815(5) 0.02905(19) Uani 1 1 d . . . C31 C 1.4472(3) -0.09403(15) 0.99613(19) 0.0248(7) Uani 1 1 d . . . C32 C 1.5416(3) -0.10484(16) 1.0617(2) 0.0316(8) Uani 1 1 d . . . F32 F 1.6407(2) -0.14808(10) 1.05787(14) 0.0450(6) Uani 1 1 d . . . C33 C 1.5408(4) -0.07100(17) 1.1313(2) 0.0390(9) Uani 1 1 d . . . F33 F 1.6355(3) -0.08286(11) 1.19211(14) 0.0597(7) Uani 1 1 d . . . C34 C 1.4437(4) -0.02531(17) 1.1382(2) 0.0381(9) Uani 1 1 d . . . F34 F 1.4411(3) 0.00660(11) 1.20603(13) 0.0562(6) Uani 1 1 d . . . C35 C 1.3515(4) -0.01169(16) 1.0740(2) 0.0335(8) Uani 1 1 d . . . F35 F 1.2580(2) 0.03462(10) 1.07918(14) 0.0463(6) Uani 1 1 d . . . C36 C 1.3545(3) -0.04533(16) 1.0051(2) 0.0272(7) Uani 1 1 d . . . F36 F 1.26301(18) -0.02992(9) 0.94274(12) 0.0346(5) Uani 1 1 d . . . N101 N 0.9628(3) -0.23965(15) 0.8345(2) 0.0390(8) Uani 1 1 d . . . C101 C 0.8524(4) -0.22330(19) 0.8659(3) 0.0449(10) Uani 1 1 d . . . H10A H 0.8617 -0.2006 0.9146 0.054 Uiso 1 1 calc R . . C102 C 0.7263(4) -0.23823(18) 0.8300(3) 0.0452(11) Uani 1 1 d . . . H10B H 0.6499 -0.2259 0.8536 0.054 Uiso 1 1 calc R . . C103 C 0.7115(4) -0.27088(19) 0.7602(3) 0.0482(11) Uani 1 1 d . . . H10C H 0.6250 -0.2811 0.7341 0.058 Uiso 1 1 calc R . . C104 C 0.8232(4) -0.2886(2) 0.7284(3) 0.0473(10) Uani 1 1 d . . . H10D H 0.8162 -0.3125 0.6806 0.057 Uiso 1 1 calc R . . C105 C 0.9463(4) -0.27132(18) 0.7670(3) 0.0422(10) Uani 1 1 d . . . H10E H 1.0236 -0.2828 0.7437 0.051 Uiso 1 1 calc R . . N201 N 1.1221(3) -0.14955(14) 1.00313(19) 0.0352(7) Uani 1 1 d . . . C201 C 1.1832(4) -0.16624(15) 1.0744(2) 0.0338(9) Uani 1 1 d . . . H20A H 1.2479 -0.2001 1.0779 0.041 Uiso 1 1 calc R . . C202 C 1.1570(4) -0.13691(17) 1.1424(2) 0.0383(9) Uani 1 1 d . . . H20B H 1.2049 -0.1490 1.1917 0.046 Uiso 1 1 calc R . . C203 C 1.0604(4) -0.08988(19) 1.1379(3) 0.0511(11) Uani 1 1 d . . . H20C H 1.0397 -0.0690 1.1843 0.061 Uiso 1 1 calc R . . C204 C 0.9933(4) -0.07300(19) 1.0655(3) 0.0503(11) Uani 1 1 d . . . H20D H 0.9247 -0.0410 1.0611 0.060 Uiso 1 1 calc R . . C205 C 1.0279(4) -0.10359(18) 1.0000(3) 0.0403(9) Uani 1 1 d . . . H20E H 0.9828 -0.0915 0.9499 0.048 Uiso 1 1 calc R . . N301 N 1.0538(4) -0.07137(16) 0.7730(2) 0.0499(9) Uani 1 1 d . . . C301 C 0.9245(5) -0.0743(2) 0.7441(3) 0.0623(13) Uani 1 1 d . . . H30B H 0.8713 -0.1074 0.7631 0.075 Uiso 1 1 calc R . . C302 C 0.8641(5) -0.0322(2) 0.6883(3) 0.0666(14) Uani 1 1 d . . . H30C H 0.7718 -0.0362 0.6691 0.080 Uiso 1 1 calc R . . C303 C 0.9400(5) 0.0157(2) 0.6610(3) 0.0582(12) Uani 1 1 d . . . H30D H 0.9012 0.0456 0.6223 0.070 Uiso 1 1 calc R . . C304 C 1.0724(4) 0.0201(2) 0.6902(3) 0.0513(11) Uani 1 1 d . . . H30E H 1.1273 0.0531 0.6726 0.062 Uiso 1 1 calc R . . C305 C 1.1238(4) -0.02441(19) 0.7456(3) 0.0462(11) Uani 1 1 d . . . H30F H 1.2160 -0.0212 0.7655 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02241(6) 0.02833(7) 0.02202(7) 0.00097(6) 0.00246(4) 0.00003(6) S1 0.0268(4) 0.0310(4) 0.0474(6) 0.0100(4) 0.0094(4) 0.0005(3) C11 0.0324(18) 0.0268(17) 0.0268(19) 0.0054(16) 0.0024(15) 0.0024(15) C12 0.037(2) 0.0305(19) 0.025(2) 0.0021(16) 0.0037(16) 0.0002(15) F12 0.0534(14) 0.0460(13) 0.0380(14) -0.0086(11) -0.0090(11) 0.0062(10) C13 0.044(2) 0.033(2) 0.035(2) 0.0020(17) 0.0119(19) 0.0094(16) F13 0.0606(15) 0.0536(14) 0.0466(15) -0.0099(12) 0.0162(12) 0.0209(12) C14 0.0295(19) 0.039(2) 0.042(2) 0.0065(19) 0.0058(18) 0.0117(16) F14 0.0350(12) 0.0702(16) 0.0727(19) -0.0034(14) 0.0056(12) 0.0194(11) C15 0.0327(19) 0.040(2) 0.037(2) 0.0016(19) -0.0021(16) 0.0008(16) F15 0.0483(14) 0.0637(15) 0.0497(16) -0.0099(13) -0.0158(12) 0.0100(11) C16 0.0365(19) 0.0261(17) 0.029(2) 0.0032(16) 0.0080(16) 0.0037(15) F16 0.0487(13) 0.0410(12) 0.0326(13) -0.0043(10) 0.0116(10) 0.0066(10) S2 0.0510(6) 0.0298(5) 0.0282(5) -0.0032(4) 0.0115(4) -0.0028(4) C21 0.0374(19) 0.0285(18) 0.0198(18) -0.0086(14) 0.0092(15) -0.0031(14) C22 0.0336(19) 0.0335(19) 0.029(2) -0.0105(17) 0.0095(16) -0.0050(15) F22 0.0335(11) 0.0543(13) 0.0546(15) -0.0031(12) 0.0093(10) -0.0130(10) C23 0.032(2) 0.042(2) 0.026(2) -0.0065(18) 0.0011(16) 0.0022(16) F23 0.0404(13) 0.0653(15) 0.0434(15) -0.0001(12) -0.0063(11) 0.0054(11) C24 0.050(2) 0.0325(19) 0.026(2) 0.0004(16) 0.0109(18) 0.0020(17) F24 0.0682(16) 0.0515(14) 0.0355(14) 0.0135(11) 0.0064(12) -0.0021(12) C25 0.036(2) 0.035(2) 0.031(2) -0.0071(17) 0.0132(17) -0.0070(16) F25 0.0445(13) 0.0518(14) 0.0586(16) 0.0099(12) 0.0155(12) -0.0150(11) C26 0.0326(19) 0.0343(19) 0.027(2) -0.0087(16) 0.0051(16) -0.0002(15) F26 0.0311(11) 0.0488(13) 0.0484(15) 0.0008(11) -0.0005(10) -0.0011(9) S3 0.0253(4) 0.0344(5) 0.0278(5) -0.0055(4) 0.0051(4) -0.0027(3) C31 0.0272(17) 0.0253(17) 0.0216(18) 0.0006(14) 0.0026(14) -0.0057(13) C32 0.0324(19) 0.0305(19) 0.031(2) -0.0002(16) 0.0009(16) -0.0005(15) F32 0.0380(12) 0.0429(12) 0.0497(15) -0.0018(11) -0.0109(11) 0.0084(10) C33 0.050(2) 0.035(2) 0.028(2) 0.0064(17) -0.0094(18) -0.0105(18) F33 0.0802(18) 0.0561(15) 0.0339(14) 0.0029(12) -0.0256(13) -0.0013(13) C34 0.057(2) 0.035(2) 0.023(2) -0.0044(17) 0.0082(19) -0.0146(18) F34 0.0899(18) 0.0500(14) 0.0302(13) -0.0116(11) 0.0129(13) -0.0127(13) C35 0.036(2) 0.0280(18) 0.038(2) -0.0019(17) 0.0119(18) -0.0030(15) F35 0.0446(12) 0.0409(12) 0.0563(16) -0.0132(11) 0.0175(11) 0.0044(10) C36 0.0263(17) 0.0290(18) 0.0262(19) 0.0031(16) 0.0033(15) -0.0027(14) F36 0.0304(10) 0.0370(11) 0.0348(12) -0.0012(10) -0.0023(9) 0.0032(8) N101 0.0261(16) 0.0441(18) 0.046(2) -0.0071(16) 0.0024(15) -0.0006(13) C101 0.041(2) 0.045(2) 0.051(3) -0.011(2) 0.015(2) -0.0047(18) C102 0.029(2) 0.040(2) 0.070(3) 0.005(2) 0.020(2) 0.0036(16) C103 0.029(2) 0.044(2) 0.068(3) 0.005(2) -0.006(2) -0.0042(17) C104 0.037(2) 0.061(3) 0.043(3) -0.010(2) 0.0021(19) -0.0087(19) C105 0.034(2) 0.048(2) 0.046(3) -0.008(2) 0.0096(19) -0.0015(17) N201 0.0386(17) 0.0312(16) 0.0359(19) -0.0003(15) 0.0057(15) 0.0042(13) C201 0.036(2) 0.0269(19) 0.040(2) 0.0070(17) 0.0108(17) 0.0061(14) C202 0.047(2) 0.039(2) 0.030(2) 0.0068(18) 0.0092(18) 0.0042(17) C203 0.069(3) 0.045(2) 0.045(3) 0.000(2) 0.029(2) 0.014(2) C204 0.047(2) 0.047(2) 0.060(3) 0.007(2) 0.019(2) 0.0247(19) C205 0.033(2) 0.042(2) 0.044(3) 0.0059(19) -0.0009(18) 0.0085(16) N301 0.050(2) 0.046(2) 0.050(2) 0.0032(18) -0.0069(18) 0.0067(17) C301 0.054(3) 0.059(3) 0.071(4) 0.015(3) 0.002(3) -0.011(2) C302 0.046(3) 0.079(3) 0.069(4) 0.011(3) -0.015(3) -0.002(2) C303 0.072(3) 0.069(3) 0.032(3) 0.016(2) -0.004(2) 0.011(3) C304 0.063(3) 0.047(2) 0.050(3) -0.001(2) 0.031(2) 0.000(2) C305 0.041(2) 0.048(2) 0.050(3) -0.015(2) 0.006(2) 0.0029(19) _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 S1 2.5916(9) . ? Bi1 S3 2.6424(8) . ? Bi1 S2 2.6447(10) . ? Bi1 N201 2.710(3) . ? Bi1 N101 2.748(3) . ? S1 C11 1.764(3) . ? C11 C16 1.380(5) . ? C11 C12 1.396(5) . ? C12 F12 1.340(4) . ? C12 C13 1.384(5) . ? C13 F13 1.345(4) . ? C13 C14 1.363(5) . ? C14 F14 1.346(4) . ? C14 C15 1.375(5) . ? C15 F15 1.342(4) . ? C15 C16 1.371(5) . ? C16 F16 1.340(4) . ? S2 C21 1.761(4) . ? C21 C26 1.390(5) . ? C21 C22 1.392(5) . ? C22 F22 1.340(4) . ? C22 C23 1.376(5) . ? C23 F23 1.341(4) . ? C23 C24 1.383(5) . ? C24 F24 1.340(4) . ? C24 C25 1.369(5) . ? C25 F25 1.347(4) . ? C25 C26 1.368(5) . ? C26 F26 1.341(4) . ? S3 C31 1.753(3) . ? C31 C36 1.392(4) . ? C31 C32 1.392(5) . ? C32 F32 1.345(4) . ? C32 C33 1.381(5) . ? C33 F33 1.341(4) . ? C33 C34 1.373(5) . ? C34 F34 1.337(4) . ? C34 C35 1.373(5) . ? C35 F35 1.351(4) . ? C35 C36 1.372(5) . ? C36 F36 1.355(4) . ? N101 C105 1.319(5) . ? N101 C101 1.340(5) . ? C101 C102 1.374(5) . ? C102 C103 1.362(6) . ? C103 C104 1.362(6) . ? C104 C105 1.375(5) . ? N201 C205 1.336(4) . ? N201 C201 1.338(5) . ? C201 C202 1.368(5) . ? C202 C203 1.368(5) . ? C203 C204 1.377(6) . ? C204 C205 1.372(6) . ? N301 C305 1.318(5) . ? N301 C301 1.335(5) . ? C301 C302 1.372(6) . ? C302 C303 1.365(6) . ? C303 C304 1.366(6) . ? C304 C305 1.369(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 S1 Bi1 S3 98.76(3) . . ? S1 Bi1 S2 86.86(3) . . ? S3 Bi1 S2 81.05(3) . . ? S1 Bi1 N201 83.36(7) . . ? S3 Bi1 N201 93.87(7) . . ? S2 Bi1 N201 168.18(6) . . ? S1 Bi1 N101 73.72(7) . . ? S3 Bi1 N101 172.17(7) . . ? S2 Bi1 N101 100.37(7) . . ? N201 Bi1 N101 83.25(9) . . ? C11 S1 Bi1 107.91(11) . . ? C16 C11 C12 116.6(3) . . ? C16 C11 S1 123.3(3) . . ? C12 C11 S1 119.9(3) . . ? F12 C12 C13 117.3(3) . . ? F12 C12 C11 121.2(3) . . ? C13 C12 C11 121.4(3) . . ? F13 C13 C14 119.7(3) . . ? F13 C13 C12 120.3(3) . . ? C14 C13 C12 120.0(3) . . ? F14 C14 C13 119.9(3) . . ? F14 C14 C15 120.2(3) . . ? C13 C14 C15 119.9(3) . . ? F15 C15 C16 120.5(3) . . ? F15 C15 C14 119.7(3) . . ? C16 C15 C14 119.8(3) . . ? F16 C16 C15 117.9(3) . . ? F16 C16 C11 119.7(3) . . ? C15 C16 C11 122.3(3) . . ? C21 S2 Bi1 102.36(11) . . ? C26 C21 C22 115.8(3) . . ? C26 C21 S2 122.1(3) . . ? C22 C21 S2 121.9(3) . . ? F22 C22 C23 117.4(3) . . ? F22 C22 C21 120.0(3) . . ? C23 C22 C21 122.6(3) . . ? F23 C23 C22 120.8(3) . . ? F23 C23 C24 119.6(3) . . ? C22 C23 C24 119.6(3) . . ? F24 C24 C25 121.1(3) . . ? F24 C24 C23 119.8(3) . . ? C25 C24 C23 119.1(3) . . ? F25 C25 C26 120.5(3) . . ? F25 C25 C24 118.8(3) . . ? C26 C25 C24 120.6(3) . . ? F26 C26 C25 117.8(3) . . ? F26 C26 C21 119.9(3) . . ? C25 C26 C21 122.2(3) . . ? C31 S3 Bi1 106.10(11) . . ? C36 C31 C32 115.1(3) . . ? C36 C31 S3 123.7(3) . . ? C32 C31 S3 121.1(3) . . ? F32 C32 C33 117.6(3) . . ? F32 C32 C31 120.0(3) . . ? C33 C32 C31 122.4(3) . . ? F33 C33 C34 120.0(4) . . ? F33 C33 C32 119.7(4) . . ? C34 C33 C32 120.3(3) . . ? F34 C34 C33 120.4(4) . . ? F34 C34 C35 120.6(4) . . ? C33 C34 C35 119.0(3) . . ? F35 C35 C36 120.4(3) . . ? F35 C35 C34 119.7(3) . . ? C36 C35 C34 119.9(3) . . ? F36 C36 C35 118.1(3) . . ? F36 C36 C31 118.7(3) . . ? C35 C36 C31 123.2(3) . . ? C105 N101 C101 117.3(3) . . ? C105 N101 Bi1 112.9(2) . . ? C101 N101 Bi1 126.2(2) . . ? N101 C101 C102 122.2(4) . . ? C103 C102 C101 119.5(4) . . ? C104 C103 C102 118.7(4) . . ? C103 C104 C105 118.8(4) . . ? N101 C105 C104 123.5(4) . . ? C205 N201 C201 117.3(3) . . ? C205 N201 Bi1 116.2(3) . . ? C201 N201 Bi1 125.1(2) . . ? N201 C201 C202 123.1(3) . . ? C203 C202 C201 118.6(4) . . ? C202 C203 C204 119.4(4) . . ? C205 C204 C203 118.3(4) . . ? N201 C205 C204 123.2(4) . . ? C305 N301 C301 116.3(4) . . ? N301 C301 C302 123.6(4) . . ? C303 C302 C301 118.4(4) . . ? C302 C303 C304 119.1(4) . . ? C303 C304 C305 118.3(4) . . ? N301 C305 C304 124.3(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.917 _refine_diff_density_min -1.421 _refine_diff_density_rms 0.098 #===END data_5 _database_code_CSD 211636 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi Cl15 S3, 3(C5 H5 N)' _chemical_formula_sum 'C33 H15 Bi Cl15 N3 S3' _chemical_formula_weight 1290.39 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 17.820(3) _cell_length_b 14.940(3) _cell_length_c 17.057(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.423(15) _cell_angle_gamma 90.00 _cell_volume 4255.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 219 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 18.78 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.014 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2480 _exptl_absorpt_coefficient_mu 5.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.771 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _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 'CCD area detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 35722 _diffrn_reflns_av_R_equivalents 0.1845 _diffrn_reflns_av_sigmaI/netI 0.1602 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7495 _reflns_number_gt 4028 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.0303P)^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 7495 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1443 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.009 _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 0.6350(6) 1.0426(7) 0.0489(7) 0.030(3) Uani 1 1 d . . . C2 C 0.6594(6) 1.0777(7) 0.1289(6) 0.028(3) Uani 1 1 d . . . C3 C 0.7047(6) 1.1583(8) 0.1480(6) 0.026(3) Uani 1 1 d . . . C4 C 0.7260(6) 1.2012(7) 0.0886(7) 0.027(3) Uani 1 1 d . . . C5 C 0.6991(6) 1.1659(8) 0.0071(7) 0.034(3) Uani 1 1 d . . . C6 C 0.6537(6) 1.0904(7) -0.0119(6) 0.023(3) Uani 1 1 d . . . C7 C 0.6147(6) 0.6411(7) 0.0518(6) 0.027(3) Uani 1 1 d . . . C8 C 0.5331(6) 0.6501(7) 0.0339(6) 0.027(3) Uani 1 1 d . . . C9 C 0.4884(6) 0.5930(7) 0.0642(6) 0.026(3) Uani 1 1 d . . . C10 C 0.5270(5) 0.5231(7) 0.1168(6) 0.021(3) Uani 1 1 d . . . C11 C 0.6071(6) 0.5092(7) 0.1357(6) 0.028(3) Uani 1 1 d . . . C12 C 0.6517(6) 0.5682(7) 0.1051(6) 0.024(3) Uani 1 1 d . . . C13 C 0.8772(5) 0.9136(7) 0.0365(7) 0.025(3) Uani 1 1 d . . . C14 C 0.9251(7) 0.8716(7) -0.0037(7) 0.034(3) Uani 1 1 d . . . C15 C 1.0092(6) 0.8783(7) 0.0290(7) 0.030(3) Uani 1 1 d . . . C16 C 1.0457(6) 0.9241(8) 0.1016(7) 0.034(3) Uani 1 1 d . . . C17 C 1.0015(6) 0.9665(7) 0.1429(7) 0.029(3) Uani 1 1 d . . . C18 C 0.9185(6) 0.9617(7) 0.1104(7) 0.030(3) Uani 1 1 d . . . C19 C 0.8860(7) 0.7056(8) 0.1080(8) 0.047(4) Uani 1 1 d . . . H19A H 0.8459 0.6850 0.0583 0.057 Uiso 1 1 calc R . . C20 C 0.9652(8) 0.6849(9) 0.1212(9) 0.054(4) Uani 1 1 d . . . H20A H 0.9793 0.6510 0.0813 0.065 Uiso 1 1 calc R . . C21 C 1.0225(9) 0.7141(11) 0.1928(11) 0.068(5) Uani 1 1 d . . . H21A H 1.0773 0.7016 0.2025 0.082 Uiso 1 1 calc R . . C22 C 1.0021(7) 0.7604(10) 0.2496(10) 0.064(5) Uani 1 1 d . . . H22A H 1.0417 0.7787 0.3007 0.077 Uiso 1 1 calc R . . C23 C 0.9205(7) 0.7814(8) 0.2318(7) 0.046(3) Uani 1 1 d . . . H23A H 0.9060 0.8165 0.2707 0.055 Uiso 1 1 calc R . . C24 C 0.5547(7) 0.7976(8) 0.1902(7) 0.036(3) Uani 1 1 d . . . H24A H 0.5298 0.8454 0.1537 0.043 Uiso 1 1 calc R . . C25 C 0.5118(7) 0.7552(8) 0.2333(8) 0.042(3) Uani 1 1 d . . . H25A H 0.4580 0.7712 0.2254 0.050 Uiso 1 1 calc R . . C26 C 0.5506(9) 0.6891(8) 0.2879(7) 0.050(4) Uani 1 1 d . . . H26A H 0.5230 0.6585 0.3185 0.060 Uiso 1 1 calc R . . C27 C 0.6274(9) 0.6658(8) 0.2995(7) 0.052(4) Uani 1 1 d . . . H27A H 0.6539 0.6199 0.3377 0.062 Uiso 1 1 calc R . . C28 C 0.6655(6) 0.7116(8) 0.2536(7) 0.037(3) Uani 1 1 d . . . H28A H 0.7199 0.6978 0.2625 0.044 Uiso 1 1 calc R . . C29 C 0.7802(10) 0.9120(10) 0.3717(10) 0.076(5) Uani 1 1 d . . . H29A H 0.7433 0.8646 0.3499 0.091 Uiso 1 1 calc R . . C30 C 0.7655(7) 0.9667(10) 0.4274(8) 0.052(4) Uani 1 1 d . . . H30A H 0.7205 0.9580 0.4442 0.062 Uiso 1 1 calc R . . C31 C 0.8159(12) 1.0324(11) 0.4575(11) 0.096(6) Uani 1 1 d . . . H31A H 0.8059 1.0748 0.4942 0.115 Uiso 1 1 calc R . . C32 C 0.8823(13) 1.0403(14) 0.4365(13) 0.138(9) Uani 1 1 d . . . H32A H 0.9215 1.0845 0.4621 0.165 Uiso 1 1 calc R . . C33 C 0.8915(14) 0.9840(17) 0.3785(13) 0.135(9) Uani 1 1 d . . . H33A H 0.9361 0.9916 0.3608 0.161 Uiso 1 1 calc R . . Bi1 Bi 0.71767(2) 0.84509(3) 0.11005(3) 0.02837(13) Uani 1 1 d . . . Cl2 Cl 0.6328(2) 1.0266(2) 0.20631(19) 0.0503(9) Uani 1 1 d . . . Cl3 Cl 0.7350(2) 1.1993(2) 0.24947(18) 0.0552(10) Uani 1 1 d . . . Cl4 Cl 0.78625(17) 1.2938(2) 0.1143(2) 0.0482(9) Uani 1 1 d . . . Cl5 Cl 0.72554(18) 1.2213(2) -0.06899(19) 0.0451(8) Uani 1 1 d . . . Cl6 Cl 0.61766(18) 1.0543(2) -0.11459(17) 0.0421(8) Uani 1 1 d . . . Cl8 Cl 0.48395(16) 0.73863(19) -0.02926(18) 0.0398(8) Uani 1 1 d . . . Cl9 Cl 0.38843(16) 0.61120(19) 0.04368(19) 0.0397(8) Uani 1 1 d . . . Cl10 Cl 0.47335(17) 0.45325(19) 0.15846(18) 0.0392(8) Uani 1 1 d . . . Cl11 Cl 0.65461(17) 0.42137(19) 0.19925(18) 0.0420(8) Uani 1 1 d . . . Cl12 Cl 0.75349(16) 0.55186(19) 0.1348(2) 0.0426(8) Uani 1 1 d . . . Cl14 Cl 0.87975(18) 0.8114(2) -0.0926(2) 0.0573(10) Uani 1 1 d . . . Cl15 Cl 1.06429(17) 0.8240(2) -0.02130(19) 0.0475(9) Uani 1 1 d . . . Cl16 Cl 1.14915(16) 0.9287(2) 0.1430(2) 0.0462(9) Uani 1 1 d . . . Cl17 Cl 1.04764(17) 1.0211(2) 0.2356(2) 0.0568(10) Uani 1 1 d . . . Cl18 Cl 0.86357(16) 1.0165(2) 0.16174(19) 0.0436(8) Uani 1 1 d . . . N2 N 0.8637(5) 0.7538(6) 0.1629(6) 0.030(2) Uani 1 1 d . . . N3 N 0.6292(5) 0.7746(6) 0.1972(5) 0.035(2) Uani 1 1 d . . . N1 N 0.8391(12) 0.9174(12) 0.3450(9) 0.105(5) Uani 1 1 d . . . S2 S 0.58768(16) 0.93622(19) 0.02569(19) 0.0345(8) Uani 1 1 d . . . S1 S 0.66958(16) 0.71129(19) 0.00956(18) 0.0319(7) Uani 1 1 d . . . S3 S 0.77237(15) 0.9063(2) -0.00620(18) 0.0337(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.024(6) 0.033(7) 0.031(7) 0.013(6) 0.005(6) 0.014(5) C2 0.025(6) 0.038(8) 0.022(7) 0.018(6) 0.007(5) 0.016(6) C3 0.022(6) 0.028(7) 0.025(6) -0.007(6) 0.003(5) 0.007(6) C4 0.023(6) 0.014(6) 0.049(8) -0.005(6) 0.019(6) 0.010(5) C5 0.034(7) 0.041(8) 0.031(7) 0.024(7) 0.017(6) 0.017(6) C6 0.028(6) 0.024(7) 0.022(6) 0.006(5) 0.016(5) 0.014(5) C7 0.025(6) 0.028(7) 0.028(6) -0.005(6) 0.010(5) -0.007(5) C8 0.027(6) 0.022(6) 0.030(6) -0.012(6) 0.009(5) -0.004(6) C9 0.017(6) 0.030(7) 0.028(6) -0.004(5) 0.006(5) 0.008(5) C10 0.015(6) 0.029(7) 0.020(6) -0.002(5) 0.006(5) 0.000(5) C11 0.038(7) 0.030(7) 0.021(6) 0.004(5) 0.018(6) 0.005(6) C12 0.023(6) 0.030(7) 0.019(6) 0.000(5) 0.006(5) 0.009(5) C13 0.008(5) 0.026(7) 0.038(7) -0.003(6) 0.003(5) -0.006(5) C14 0.046(8) 0.020(7) 0.034(7) -0.001(5) 0.012(6) 0.002(5) C15 0.032(7) 0.036(8) 0.028(7) 0.006(6) 0.018(6) 0.015(5) C16 0.011(6) 0.043(8) 0.048(8) 0.000(7) 0.011(6) -0.001(5) C17 0.023(6) 0.030(7) 0.035(7) -0.003(6) 0.011(6) -0.007(5) C18 0.025(6) 0.025(7) 0.046(8) 0.011(6) 0.021(6) -0.001(5) C19 0.042(8) 0.050(9) 0.052(9) 0.015(7) 0.017(7) 0.018(7) C20 0.057(9) 0.055(10) 0.063(10) 0.018(8) 0.036(9) 0.018(8) C21 0.047(10) 0.094(13) 0.084(13) 0.064(11) 0.049(10) 0.029(9) C22 0.018(7) 0.083(12) 0.070(11) 0.052(9) -0.011(7) -0.017(7) C23 0.052(9) 0.052(9) 0.032(8) 0.000(7) 0.013(7) -0.016(7) C24 0.039(8) 0.034(7) 0.034(7) -0.001(6) 0.011(6) 0.010(6) C25 0.048(8) 0.029(8) 0.059(9) -0.002(7) 0.034(7) 0.002(6) C26 0.093(12) 0.042(9) 0.031(8) -0.009(7) 0.042(8) -0.018(8) C27 0.078(10) 0.033(8) 0.028(7) 0.008(7) -0.003(7) -0.004(8) C28 0.022(6) 0.036(8) 0.037(8) -0.007(6) -0.009(6) 0.005(6) C29 0.104(14) 0.062(11) 0.074(12) -0.008(9) 0.046(11) 0.007(10) C30 0.040(8) 0.054(10) 0.061(10) 0.012(8) 0.019(8) 0.007(8) C31 0.137(17) 0.067(13) 0.111(15) -0.015(11) 0.077(14) -0.034(12) C32 0.18(2) 0.14(2) 0.127(18) -0.078(15) 0.104(17) -0.120(17) C33 0.16(2) 0.17(3) 0.109(18) -0.046(17) 0.089(17) -0.052(19) Bi1 0.0206(2) 0.0246(2) 0.0394(3) 0.0014(3) 0.00998(18) 0.0017(2) Cl2 0.077(2) 0.045(2) 0.0410(19) 0.0105(16) 0.0364(18) 0.0045(18) Cl3 0.077(2) 0.048(2) 0.0312(18) -0.0081(16) 0.0075(18) 0.0093(18) Cl4 0.0338(17) 0.0333(18) 0.069(2) 0.0005(17) 0.0067(17) -0.0049(14) Cl5 0.051(2) 0.043(2) 0.057(2) 0.0224(16) 0.0389(17) 0.0141(16) Cl6 0.055(2) 0.042(2) 0.0249(16) 0.0002(14) 0.0086(15) 0.0157(16) Cl8 0.0328(17) 0.0313(18) 0.053(2) 0.0109(15) 0.0113(16) 0.0083(14) Cl9 0.0260(15) 0.0376(18) 0.056(2) 0.0027(16) 0.0152(15) 0.0056(13) Cl10 0.0416(17) 0.0387(19) 0.0426(18) 0.0053(15) 0.0214(15) 0.0006(14) Cl11 0.0411(18) 0.0387(19) 0.0411(18) 0.0118(15) 0.0081(15) 0.0063(15) Cl12 0.0211(15) 0.0390(19) 0.063(2) 0.0149(16) 0.0082(15) 0.0030(14) Cl14 0.0410(19) 0.080(3) 0.048(2) -0.0275(19) 0.0109(17) -0.0033(17) Cl15 0.0361(17) 0.061(3) 0.053(2) -0.0109(17) 0.0251(16) 0.0077(15) Cl16 0.0201(15) 0.053(2) 0.062(2) -0.0055(17) 0.0100(15) 0.0007(14) Cl17 0.0374(18) 0.066(2) 0.061(2) -0.0366(19) 0.0089(17) -0.0095(17) Cl18 0.0330(17) 0.046(2) 0.056(2) -0.0162(17) 0.0213(16) -0.0006(15) N2 0.022(5) 0.036(6) 0.031(6) 0.007(5) 0.008(5) 0.002(4) N3 0.038(6) 0.038(7) 0.026(6) -0.006(5) 0.009(5) 0.003(5) N1 0.148(16) 0.115(15) 0.091(12) 0.003(10) 0.090(13) 0.034(12) S2 0.0244(16) 0.0275(18) 0.048(2) 0.0033(15) 0.0085(15) 0.0059(13) S1 0.0274(16) 0.0288(18) 0.0404(18) 0.0008(14) 0.0128(15) -0.0010(13) S3 0.0200(15) 0.046(2) 0.0336(18) 0.0065(15) 0.0078(14) 0.0007(14) _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 C2 1.382(14) . ? C1 C6 1.392(14) . ? C1 S2 1.778(11) . ? C2 C3 1.422(14) . ? C2 Cl2 1.728(11) . ? C3 C4 1.362(14) . ? C3 Cl3 1.735(10) . ? C4 C5 1.405(14) . ? C4 Cl4 1.710(11) . ? C5 C6 1.360(14) . ? C5 Cl5 1.737(11) . ? C6 Cl6 1.729(10) . ? C7 C8 1.384(13) . ? C7 C12 1.425(13) . ? C7 S1 1.751(11) . ? C8 C9 1.385(14) . ? C8 Cl8 1.737(11) . ? C9 C10 1.391(13) . ? C9 Cl9 1.713(10) . ? C10 C11 1.366(13) . ? C10 Cl10 1.726(10) . ? C11 C12 1.403(14) . ? C11 Cl11 1.725(10) . ? C12 Cl12 1.723(10) . ? C13 C18 1.414(14) . ? C13 C14 1.414(14) . ? C13 S3 1.756(9) . ? C14 C15 1.408(14) . ? C14 Cl14 1.705(11) . ? C15 C16 1.364(14) . ? C15 Cl15 1.716(10) . ? C16 C17 1.380(14) . ? C16 Cl16 1.731(10) . ? C17 C18 1.389(13) . ? C17 Cl17 1.713(11) . ? C18 Cl18 1.730(11) . ? C19 N2 1.347(14) . ? C19 C20 1.384(16) . ? C20 C21 1.361(18) . ? C21 C22 1.340(19) . ? C22 C23 1.414(16) . ? C23 N2 1.321(13) . ? C24 N3 1.336(13) . ? C24 C25 1.386(15) . ? C25 C26 1.368(15) . ? C26 C27 1.358(17) . ? C27 C28 1.383(16) . ? C28 N3 1.340(13) . ? C29 N1 1.285(19) . ? C29 C30 1.347(18) . ? C30 C31 1.308(18) . ? C31 C32 1.35(2) . ? C32 C33 1.35(2) . ? C33 N1 1.35(2) . ? Bi1 S1 2.577(3) . ? Bi1 S2 2.639(3) . ? Bi1 S3 2.659(3) . ? Bi1 N3 2.728(9) . ? Bi1 N2 2.795(8) . ? 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 C2 C1 C6 117.8(10) . . ? C2 C1 S2 121.4(9) . . ? C6 C1 S2 120.7(9) . . ? C1 C2 C3 120.4(10) . . ? C1 C2 Cl2 120.7(9) . . ? C3 C2 Cl2 118.9(8) . . ? C4 C3 C2 120.8(9) . . ? C4 C3 Cl3 120.4(9) . . ? C2 C3 Cl3 118.8(9) . . ? C3 C4 C5 118.1(10) . . ? C3 C4 Cl4 120.2(9) . . ? C5 C4 Cl4 121.7(9) . . ? C6 C5 C4 121.1(10) . . ? C6 C5 Cl5 120.7(9) . . ? C4 C5 Cl5 118.2(9) . . ? C5 C6 C1 121.7(10) . . ? C5 C6 Cl6 118.7(8) . . ? C1 C6 Cl6 119.6(9) . . ? C8 C7 C12 115.5(10) . . ? C8 C7 S1 123.1(9) . . ? C12 C7 S1 121.3(8) . . ? C7 C8 C9 123.7(10) . . ? C7 C8 Cl8 118.3(9) . . ? C9 C8 Cl8 118.0(7) . . ? C8 C9 C10 119.0(9) . . ? C8 C9 Cl9 121.2(8) . . ? C10 C9 Cl9 119.7(8) . . ? C11 C10 C9 120.4(10) . . ? C11 C10 Cl10 119.6(8) . . ? C9 C10 Cl10 119.9(8) . . ? C10 C11 C12 119.9(9) . . ? C10 C11 Cl11 120.5(9) . . ? C12 C11 Cl11 119.6(8) . . ? C11 C12 C7 121.5(9) . . ? C11 C12 Cl12 118.5(8) . . ? C7 C12 Cl12 120.1(8) . . ? C18 C13 C14 116.3(9) . . ? C18 C13 S3 123.2(8) . . ? C14 C13 S3 120.4(8) . . ? C15 C14 C13 121.0(10) . . ? C15 C14 Cl14 119.9(9) . . ? C13 C14 Cl14 119.1(8) . . ? C16 C15 C14 119.9(10) . . ? C16 C15 Cl15 121.1(9) . . ? C14 C15 Cl15 118.9(9) . . ? C15 C16 C17 121.2(9) . . ? C15 C16 Cl16 119.5(9) . . ? C17 C16 Cl16 119.3(9) . . ? C16 C17 C18 119.4(10) . . ? C16 C17 Cl17 121.0(8) . . ? C18 C17 Cl17 119.6(9) . . ? C17 C18 C13 122.2(10) . . ? C17 C18 Cl18 119.0(9) . . ? C13 C18 Cl18 118.8(8) . . ? N2 C19 C20 122.5(12) . . ? C21 C20 C19 118.5(14) . . ? C22 C21 C20 120.5(13) . . ? C21 C22 C23 118.5(14) . . ? N2 C23 C22 122.2(13) . . ? N3 C24 C25 123.4(11) . . ? C26 C25 C24 116.7(12) . . ? C27 C26 C25 121.9(12) . . ? C26 C27 C28 117.4(12) . . ? N3 C28 C27 123.0(11) . . ? N1 C29 C30 126.6(17) . . ? C31 C30 C29 117.1(15) . . ? C30 C31 C32 120.4(17) . . ? C33 C32 C31 118.6(18) . . ? N1 C33 C32 122(2) . . ? S1 Bi1 S2 90.73(9) . . ? S1 Bi1 S3 83.94(9) . . ? S2 Bi1 S3 84.05(9) . . ? S1 Bi1 N3 86.67(19) . . ? S2 Bi1 N3 86.1(2) . . ? S3 Bi1 N3 166.28(19) . . ? S1 Bi1 N2 83.8(2) . . ? S2 Bi1 N2 165.8(2) . . ? S3 Bi1 N2 82.30(19) . . ? N3 Bi1 N2 106.6(3) . . ? C23 N2 C19 117.7(10) . . ? C23 N2 Bi1 118.2(8) . . ? C19 N2 Bi1 120.3(7) . . ? C24 N3 C28 117.5(10) . . ? C24 N3 Bi1 126.7(8) . . ? C28 N3 Bi1 115.9(8) . . ? C29 N1 C33 115.2(17) . . ? C1 S2 Bi1 94.7(3) . . ? C7 S1 Bi1 107.1(4) . . ? C13 S3 Bi1 109.0(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.777 _refine_diff_density_min -1.147 _refine_diff_density_rms 0.184 #===END data_6 _database_code_CSD 211637 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi F15 S3, 3(C6 H7 N)' _chemical_formula_sum 'C36 H21 Bi F15 N3 S3' _chemical_formula_weight 1085.72 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' 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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3018(12) _cell_length_b 17.925(2) _cell_length_c 23.774(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.982(2) _cell_angle_gamma 90.00 _cell_volume 3915.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 997 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 26.11 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 4.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.192 _exptl_absorpt_correction_T_max 0.238 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 25092 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.51 _reflns_number_total 8904 _reflns_number_gt 6592 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.0188P)^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 SHELXL _refine_ls_extinction_coef 0.00018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8904 _refine_ls_number_parameters 527 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0518 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 0.670836(14) 0.137348(7) 0.799168(5) 0.02931(5) Uani 1 1 d . . . S1 S 0.89484(11) 0.07628(6) 0.76082(4) 0.0458(3) Uani 1 1 d . . . S2 S 0.84276(10) 0.14443(5) 0.89846(4) 0.0377(2) Uani 1 1 d . . . S3 S 0.77722(10) 0.27085(5) 0.77928(4) 0.0367(2) Uani 1 1 d . . . N1 N 0.4463(3) 0.19893(16) 0.84681(15) 0.0422(8) Uani 1 1 d . . . N2 N 0.5190(3) 0.15389(15) 0.68911(12) 0.0375(7) Uani 1 1 d . . . N3 N 0.5643(3) 0.00227(16) 0.83187(12) 0.0379(7) Uani 1 1 d . . . F12 F 1.0178(3) 0.14772(13) 0.66597(10) 0.0654(7) Uani 1 1 d . . . F13 F 0.9360(3) 0.13022(14) 0.55349(10) 0.0780(8) Uani 1 1 d . . . F14 F 0.7081(3) 0.04173(14) 0.51309(10) 0.0720(8) Uani 1 1 d . . . F15 F 0.5604(3) -0.02966(12) 0.58705(10) 0.0645(7) Uani 1 1 d . . . F16 F 0.6425(2) -0.01536(12) 0.69976(9) 0.0540(6) Uani 1 1 d . . . F22 F 0.6400(2) 0.07277(11) 0.96981(8) 0.0427(5) Uani 1 1 d . . . F23 F 0.6479(2) -0.06767(12) 1.00973(9) 0.0480(5) Uani 1 1 d . . . F24 F 0.8562(2) -0.16318(11) 0.98770(9) 0.0479(6) Uani 1 1 d . . . F25 F 1.0650(2) -0.11634(11) 0.92781(9) 0.0453(5) Uani 1 1 d . . . F26 F 1.0593(2) 0.02273(11) 0.88648(8) 0.0445(5) Uani 1 1 d . . . F32 F 0.5460(3) 0.34770(12) 0.69508(9) 0.0590(7) Uani 1 1 d . . . F33 F 0.3301(3) 0.43537(14) 0.71842(11) 0.0821(9) Uani 1 1 d . . . F35 F 0.5006(3) 0.41444(12) 0.91408(10) 0.0627(7) Uani 1 1 d . . . F34 F 0.3046(3) 0.46874(13) 0.82758(12) 0.0805(8) Uani 1 1 d . . . F36 F 0.7150(2) 0.32478(12) 0.89187(8) 0.0485(6) Uani 1 1 d . . . C11 C 0.8333(4) 0.0654(2) 0.68690(15) 0.0381(9) Uani 1 1 d . . . C12 C 0.9043(4) 0.1025(2) 0.64778(17) 0.0440(10) Uani 1 1 d . . . C13 C 0.8639(5) 0.0942(2) 0.59038(17) 0.0494(10) Uani 1 1 d . . . C14 C 0.7478(5) 0.0497(2) 0.56930(16) 0.0464(10) Uani 1 1 d . . . C15 C 0.6747(4) 0.0138(2) 0.60697(18) 0.0441(10) Uani 1 1 d . . . C16 C 0.7176(4) 0.02146(19) 0.66456(17) 0.0410(9) Uani 1 1 d . . . C21 C 0.8458(3) 0.05246(18) 0.92473(13) 0.0302(8) Uani 1 1 d . . . C22 C 0.7457(4) 0.02650(19) 0.95806(14) 0.0325(8) Uani 1 1 d . . . C23 C 0.7483(4) -0.0444(2) 0.97887(14) 0.0321(8) Uani 1 1 d . . . C24 C 0.8540(4) -0.09303(19) 0.96809(14) 0.0334(8) Uani 1 1 d . . . C25 C 0.9583(4) -0.06993(19) 0.93674(14) 0.0328(8) Uani 1 1 d . . . C26 C 0.9536(4) 0.0021(2) 0.91551(14) 0.0323(8) Uani 1 1 d . . . C31 C 0.6361(4) 0.33083(18) 0.79294(15) 0.0335(9) Uani 1 1 d . . . C32 C 0.5357(4) 0.3618(2) 0.75008(16) 0.0424(9) Uani 1 1 d . . . C33 C 0.4260(4) 0.4077(2) 0.7612(2) 0.0533(12) Uani 1 1 d . . . C34 C 0.4122(5) 0.4243(2) 0.8161(2) 0.0511(11) Uani 1 1 d . . . C35 C 0.5113(5) 0.3967(2) 0.85990(17) 0.0446(10) Uani 1 1 d . . . C36 C 0.6210(4) 0.35108(18) 0.84806(15) 0.0357(9) Uani 1 1 d . . . C101 C 0.3236(4) 0.2183(2) 0.81353(18) 0.0519(11) Uani 1 1 d . . . H101 H 0.3142 0.2075 0.7749 0.062 Uiso 1 1 calc R . . C102 C 0.2095(4) 0.2535(2) 0.83328(19) 0.0542(12) Uani 1 1 d . . . H102 H 0.1257 0.2658 0.8082 0.065 Uiso 1 1 calc R . . C103 C 0.2203(4) 0.2706(2) 0.89064(18) 0.0436(10) Uani 1 1 d . . . C104 C 0.3469(4) 0.25060(19) 0.92485(17) 0.0431(9) Uani 1 1 d . . . H104 H 0.3593 0.2609 0.9636 0.052 Uiso 1 1 calc R . . C105 C 0.4557(4) 0.2153(2) 0.90192(18) 0.0439(10) Uani 1 1 d . . . H105 H 0.5402 0.2021 0.9262 0.053 Uiso 1 1 calc R . . C106 C 0.1008(4) 0.3113(2) 0.9138(2) 0.0639(13) Uani 1 1 d . . . H10A H 0.0659 0.2811 0.9421 0.096 Uiso 1 1 calc R . . H10B H 0.0224 0.3213 0.8834 0.096 Uiso 1 1 calc R . . H10C H 0.1378 0.3575 0.9306 0.096 Uiso 1 1 calc R . . C201 C 0.5674(4) 0.19479(19) 0.64901(16) 0.0397(9) Uani 1 1 d . . . H201 H 0.6510 0.2233 0.6592 0.048 Uiso 1 1 calc R . . C202 C 0.4994(4) 0.19670(19) 0.59344(16) 0.0411(9) Uani 1 1 d . . . H202 H 0.5368 0.2263 0.5671 0.049 Uiso 1 1 calc R . . C203 C 0.3766(4) 0.1551(2) 0.57673(15) 0.0393(9) Uani 1 1 d . . . C204 C 0.3265(4) 0.1120(2) 0.61781(16) 0.0437(10) Uani 1 1 d . . . H204 H 0.2442 0.0824 0.6083 0.052 Uiso 1 1 calc R . . C205 C 0.3987(4) 0.1131(2) 0.67253(15) 0.0413(9) Uani 1 1 d . . . H205 H 0.3626 0.0842 0.6997 0.050 Uiso 1 1 calc R . . C206 C 0.2988(5) 0.1564(2) 0.51624(17) 0.0636(13) Uani 1 1 d . . . H20A H 0.3081 0.2050 0.5002 0.095 Uiso 1 1 calc R . . H20B H 0.1976 0.1452 0.5157 0.095 Uiso 1 1 calc R . . H20C H 0.3409 0.1198 0.4942 0.095 Uiso 1 1 calc R . . C301 C 0.6216(4) -0.0648(2) 0.82564(15) 0.0445(10) Uani 1 1 d . . . H301 H 0.6994 -0.0682 0.8055 0.053 Uiso 1 1 calc R . . C302 C 0.5722(4) -0.1288(2) 0.84727(16) 0.0474(10) Uani 1 1 d . . . H302 H 0.6147 -0.1744 0.8408 0.057 Uiso 1 1 calc R . . C303 C 0.4585(4) -0.12612(19) 0.87892(16) 0.0407(9) Uani 1 1 d . . . C304 C 0.4000(4) -0.05694(19) 0.88508(15) 0.0374(9) Uani 1 1 d . . . H304 H 0.3235 -0.0518 0.9057 0.045 Uiso 1 1 calc R . . C305 C 0.4528(4) 0.0045(2) 0.86125(15) 0.0363(9) Uani 1 1 d . . . H305 H 0.4089 0.0503 0.8656 0.044 Uiso 1 1 calc R . . C306 C 0.4014(5) -0.1944(2) 0.9054(2) 0.0769(15) Uani 1 1 d . . . H30A H 0.3549 -0.1796 0.9370 0.115 Uiso 1 1 calc R . . H30B H 0.4808 -0.2274 0.9186 0.115 Uiso 1 1 calc R . . H30C H 0.3323 -0.2195 0.8776 0.115 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02984(7) 0.03110(7) 0.02742(7) 0.00193(7) 0.00581(5) 0.00112(7) S1 0.0403(6) 0.0596(7) 0.0384(6) -0.0041(5) 0.0094(4) 0.0134(5) S2 0.0391(5) 0.0360(5) 0.0361(5) 0.0014(4) -0.0003(4) 0.0000(4) S3 0.0363(5) 0.0360(5) 0.0376(5) 0.0028(4) 0.0049(4) -0.0048(4) N1 0.0368(19) 0.0335(18) 0.058(2) 0.0024(16) 0.0129(16) 0.0024(14) N2 0.0435(19) 0.0366(18) 0.0317(17) 0.0010(13) 0.0035(14) -0.0054(14) N3 0.0381(18) 0.0410(18) 0.0355(18) 0.0014(14) 0.0089(14) -0.0013(14) F12 0.0545(15) 0.0779(18) 0.0665(17) -0.0052(13) 0.0175(12) -0.0240(13) F13 0.095(2) 0.092(2) 0.0537(17) 0.0115(14) 0.0319(14) -0.0217(17) F14 0.104(2) 0.0721(17) 0.0380(15) -0.0042(12) 0.0044(14) -0.0044(15) F15 0.0744(18) 0.0491(15) 0.0666(17) -0.0090(12) -0.0003(13) -0.0155(13) F16 0.0608(15) 0.0472(14) 0.0562(15) 0.0105(11) 0.0161(12) -0.0071(11) F22 0.0358(12) 0.0493(13) 0.0454(13) -0.0005(10) 0.0135(9) 0.0139(10) F23 0.0425(13) 0.0577(14) 0.0477(14) 0.0072(11) 0.0188(10) 0.0004(11) F24 0.0545(14) 0.0383(12) 0.0525(15) 0.0111(10) 0.0135(11) 0.0057(10) F25 0.0430(13) 0.0455(13) 0.0494(14) 0.0006(10) 0.0137(10) 0.0166(10) F26 0.0351(12) 0.0570(14) 0.0449(13) 0.0082(10) 0.0173(10) 0.0057(10) F32 0.0794(17) 0.0553(15) 0.0362(14) 0.0063(11) -0.0105(12) 0.0054(12) F33 0.0756(19) 0.0708(18) 0.086(2) 0.0165(15) -0.0325(16) 0.0235(14) F35 0.0804(18) 0.0526(15) 0.0587(17) -0.0137(12) 0.0217(13) 0.0012(13) F34 0.0694(19) 0.0573(16) 0.114(2) -0.0048(15) 0.0124(16) 0.0272(14) F36 0.0543(14) 0.0562(13) 0.0308(12) 0.0021(10) -0.0071(10) 0.0063(11) C11 0.043(2) 0.039(2) 0.035(2) -0.0067(16) 0.0141(18) 0.0097(18) C12 0.043(2) 0.042(2) 0.049(3) -0.0055(19) 0.0145(19) -0.0030(18) C13 0.064(3) 0.048(2) 0.040(3) 0.006(2) 0.022(2) -0.003(2) C14 0.065(3) 0.042(2) 0.031(2) -0.0047(18) 0.005(2) 0.008(2) C15 0.055(3) 0.027(2) 0.049(3) -0.0025(18) 0.003(2) 0.0009(18) C16 0.048(2) 0.030(2) 0.048(3) 0.0070(18) 0.0149(19) 0.0042(17) C21 0.0265(19) 0.039(2) 0.0230(18) -0.0035(15) -0.0021(14) 0.0027(15) C22 0.0241(19) 0.043(2) 0.029(2) -0.0070(16) 0.0008(15) 0.0069(15) C23 0.0265(19) 0.044(2) 0.0262(19) 0.0044(16) 0.0058(15) -0.0016(16) C24 0.033(2) 0.038(2) 0.029(2) 0.0045(16) 0.0013(15) 0.0033(16) C25 0.0280(19) 0.038(2) 0.032(2) -0.0039(16) 0.0036(15) 0.0096(15) C26 0.0260(19) 0.046(2) 0.0256(19) 0.0001(16) 0.0048(15) 0.0008(16) C31 0.036(2) 0.0237(17) 0.037(2) 0.0055(16) -0.0035(17) -0.0067(14) C32 0.054(2) 0.035(2) 0.035(2) 0.0027(19) -0.0044(18) -0.003(2) C33 0.049(3) 0.042(2) 0.061(3) 0.014(2) -0.018(2) 0.000(2) C34 0.051(3) 0.029(2) 0.073(3) 0.000(2) 0.007(2) 0.0076(18) C35 0.059(3) 0.032(2) 0.043(3) -0.0032(18) 0.008(2) -0.0040(19) C36 0.044(2) 0.027(2) 0.034(2) 0.0035(16) -0.0015(17) -0.0024(16) C101 0.046(3) 0.052(3) 0.057(3) -0.015(2) 0.006(2) -0.001(2) C102 0.033(2) 0.059(3) 0.068(3) -0.013(2) -0.002(2) 0.0044(19) C103 0.038(2) 0.031(2) 0.065(3) -0.0069(19) 0.016(2) -0.0011(17) C104 0.045(2) 0.036(2) 0.051(3) 0.0019(18) 0.0157(19) 0.0032(17) C105 0.043(2) 0.038(2) 0.052(3) 0.0127(19) 0.0115(19) 0.0054(18) C106 0.042(3) 0.060(3) 0.094(4) -0.023(3) 0.023(2) 0.008(2) C201 0.043(2) 0.033(2) 0.042(2) 0.0013(17) 0.0059(18) -0.0046(17) C202 0.057(3) 0.031(2) 0.038(2) 0.0060(17) 0.0143(19) 0.0009(18) C203 0.044(2) 0.043(2) 0.031(2) -0.0044(16) 0.0034(17) 0.0073(17) C204 0.033(2) 0.054(2) 0.044(2) -0.0113(19) 0.0029(17) -0.0091(17) C205 0.047(2) 0.047(2) 0.030(2) 0.0000(17) 0.0070(17) -0.0078(18) C206 0.064(3) 0.083(3) 0.040(3) -0.003(2) -0.003(2) 0.000(2) C301 0.047(2) 0.053(3) 0.035(2) -0.0008(19) 0.0108(18) 0.004(2) C302 0.058(3) 0.037(2) 0.050(3) -0.0050(19) 0.017(2) 0.012(2) C303 0.043(2) 0.033(2) 0.047(2) -0.0001(17) 0.0103(18) 0.0021(17) C304 0.036(2) 0.041(2) 0.037(2) -0.0001(17) 0.0107(16) -0.0030(17) C305 0.034(2) 0.035(2) 0.039(2) -0.0032(17) 0.0036(17) 0.0039(16) C306 0.096(4) 0.047(3) 0.100(4) 0.013(3) 0.053(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 S1 2.6390(10) . ? Bi1 S2 2.6395(9) . ? Bi1 S3 2.6599(9) . ? Bi1 N1 2.757(3) . ? Bi1 N3 2.773(3) . ? Bi1 N2 2.788(3) . ? S1 C11 1.772(4) . ? S2 C21 1.762(3) . ? S3 C31 1.765(4) . ? N1 C101 1.329(5) . ? N1 C105 1.332(4) . ? N2 C201 1.335(4) . ? N2 C205 1.343(4) . ? N3 C301 1.332(4) . ? N3 C305 1.339(4) . ? F12 C12 1.348(4) . ? F13 C13 1.349(4) . ? F14 C14 1.337(4) . ? F15 C15 1.344(4) . ? F16 C16 1.345(4) . ? F22 C22 1.349(4) . ? F23 C23 1.341(4) . ? F24 C24 1.340(4) . ? F25 C25 1.337(4) . ? F26 C26 1.339(4) . ? F32 C32 1.350(4) . ? F33 C33 1.338(4) . ? F35 C35 1.345(4) . ? F34 C34 1.340(4) . ? F36 C36 1.337(4) . ? C11 C16 1.371(5) . ? C11 C12 1.391(5) . ? C12 C13 1.366(5) . ? C13 C14 1.373(5) . ? C14 C15 1.367(5) . ? C15 C16 1.372(5) . ? C21 C26 1.391(4) . ? C21 C22 1.393(5) . ? C22 C23 1.362(5) . ? C23 C24 1.369(5) . ? C24 C25 1.376(5) . ? C25 C26 1.385(5) . ? C31 C32 1.386(5) . ? C31 C36 1.388(5) . ? C32 C33 1.368(6) . ? C33 C34 1.366(6) . ? C34 C35 1.370(5) . ? C35 C36 1.371(5) . ? C101 C102 1.379(5) . ? C102 C103 1.386(5) . ? C103 C104 1.370(5) . ? C103 C106 1.504(5) . ? C104 C105 1.377(5) . ? C201 C202 1.373(5) . ? C202 C203 1.370(5) . ? C203 C204 1.381(5) . ? C203 C206 1.506(5) . ? C204 C205 1.368(5) . ? C301 C302 1.367(5) . ? C302 C303 1.391(5) . ? C303 C304 1.371(5) . ? C303 C306 1.510(5) . ? C304 C305 1.364(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 S1 Bi1 S2 85.87(3) . . ? S1 Bi1 S3 88.63(3) . . ? S2 Bi1 S3 85.73(3) . . ? S1 Bi1 N1 176.01(7) . . ? S2 Bi1 N1 90.31(7) . . ? S3 Bi1 N1 92.27(6) . . ? S1 Bi1 N3 94.05(7) . . ? S2 Bi1 N3 89.11(6) . . ? S3 Bi1 N3 174.00(6) . . ? N1 Bi1 N3 84.70(9) . . ? S1 Bi1 N2 91.80(7) . . ? S2 Bi1 N2 168.96(6) . . ? S3 Bi1 N2 83.42(6) . . ? N1 Bi1 N2 92.16(9) . . ? N3 Bi1 N2 101.84(8) . . ? C11 S1 Bi1 103.77(12) . . ? C21 S2 Bi1 104.25(10) . . ? C31 S3 Bi1 101.97(11) . . ? C101 N1 C105 116.5(3) . . ? C101 N1 Bi1 119.7(3) . . ? C105 N1 Bi1 123.7(2) . . ? C201 N2 C205 116.6(3) . . ? C201 N2 Bi1 123.4(2) . . ? C205 N2 Bi1 119.6(2) . . ? C301 N3 C305 116.1(3) . . ? C301 N3 Bi1 126.1(3) . . ? C305 N3 Bi1 117.4(2) . . ? C16 C11 C12 116.2(3) . . ? C16 C11 S1 124.0(3) . . ? C12 C11 S1 119.8(3) . . ? F12 C12 C13 117.8(3) . . ? F12 C12 C11 120.2(4) . . ? C13 C12 C11 122.1(4) . . ? F13 C13 C12 120.7(4) . . ? F13 C13 C14 118.9(4) . . ? C12 C13 C14 120.4(4) . . ? F14 C14 C15 121.1(4) . . ? F14 C14 C13 120.4(4) . . ? C15 C14 C13 118.5(4) . . ? F15 C15 C14 119.3(4) . . ? F15 C15 C16 120.1(4) . . ? C14 C15 C16 120.6(4) . . ? F16 C16 C11 119.6(4) . . ? F16 C16 C15 118.2(3) . . ? C11 C16 C15 122.2(4) . . ? C26 C21 C22 115.8(3) . . ? C26 C21 S2 121.6(3) . . ? C22 C21 S2 122.6(3) . . ? F22 C22 C23 118.0(3) . . ? F22 C22 C21 119.1(3) . . ? C23 C22 C21 122.9(3) . . ? F23 C23 C22 121.0(3) . . ? F23 C23 C24 119.1(3) . . ? C22 C23 C24 119.9(3) . . ? F24 C24 C23 120.4(3) . . ? F24 C24 C25 119.8(3) . . ? C23 C24 C25 119.8(3) . . ? F25 C25 C24 120.2(3) . . ? F25 C25 C26 120.3(3) . . ? C24 C25 C26 119.5(3) . . ? F26 C26 C25 117.5(3) . . ? F26 C26 C21 120.5(3) . . ? C25 C26 C21 122.0(3) . . ? C32 C31 C36 115.7(4) . . ? C32 C31 S3 122.9(3) . . ? C36 C31 S3 121.4(3) . . ? F32 C32 C33 117.8(3) . . ? F32 C32 C31 119.7(4) . . ? C33 C32 C31 122.5(4) . . ? F33 C33 C34 119.6(4) . . ? F33 C33 C32 120.4(4) . . ? C34 C33 C32 120.0(4) . . ? F34 C34 C33 120.6(4) . . ? F34 C34 C35 119.7(4) . . ? C33 C34 C35 119.7(4) . . ? F35 C35 C34 120.0(4) . . ? F35 C35 C36 120.4(3) . . ? C34 C35 C36 119.6(4) . . ? F36 C36 C35 117.9(3) . . ? F36 C36 C31 119.5(3) . . ? C35 C36 C31 122.6(3) . . ? N1 C101 C102 123.5(4) . . ? C101 C102 C103 119.7(4) . . ? C104 C103 C102 116.7(4) . . ? C104 C103 C106 121.7(4) . . ? C102 C103 C106 121.5(4) . . ? C103 C104 C105 120.2(4) . . ? N1 C105 C104 123.4(4) . . ? N2 C201 C202 123.0(3) . . ? C203 C202 C201 120.2(3) . . ? C202 C203 C204 117.2(3) . . ? C202 C203 C206 121.5(4) . . ? C204 C203 C206 121.3(4) . . ? C205 C204 C203 119.6(3) . . ? N2 C205 C204 123.4(3) . . ? N3 C301 C302 123.5(4) . . ? C301 C302 C303 120.2(4) . . ? C304 C303 C302 115.9(4) . . ? C304 C303 C306 121.1(4) . . ? C302 C303 C306 122.9(4) . . ? C305 C304 C303 120.7(4) . . ? N3 C305 C304 123.5(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.537 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.089 #===END data_7 _database_code_CSD 211638 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi Cl15 S3, 2(C6H7N)' _chemical_formula_sum 'C30 H14 Bi Cl15 N2 S3' _chemical_formula_weight 1239.34 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/C _symmetry_space_group_name_Hall '-P 2ybc' 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 8.7882(7) _cell_length_b 10.3833(8) _cell_length_c 44.413(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.538(2) _cell_angle_gamma 90.00 _cell_volume 4040.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5291 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 23.92 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2376 _exptl_absorpt_coefficient_mu 5.540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.400 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details 'SADABS (Shedrick, 1998)' _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 40850 _diffrn_reflns_av_R_equivalents 0.1237 _diffrn_reflns_av_sigmaI/netI 0.1082 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -57 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.53 _reflns_number_total 9280 _reflns_number_gt 6136 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.0545P)^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 SHELXL _refine_ls_extinction_coef 0.00291(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9280 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1237 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1339 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 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 0.08232(4) 1.08261(4) 0.388669(8) 0.02547(14) Uani 1 1 d . . . C11 C -0.0607(11) 1.0019(8) 0.45500(19) 0.019(2) Uani 1 1 d . . . C12 C -0.2062(11) 0.9594(9) 0.46054(19) 0.022(2) Uani 1 1 d . . . C13 C -0.2300(11) 0.8422(9) 0.4750(2) 0.024(2) Uani 1 1 d . . . C14 C -0.1091(11) 0.7647(8) 0.48409(19) 0.020(2) Uani 1 1 d . . . C15 C 0.0418(11) 0.8047(9) 0.4790(2) 0.024(2) Uani 1 1 d . . . C16 C 0.0636(9) 0.9217(9) 0.46441(18) 0.0187(18) Uani 1 1 d . . . C21 C 0.1617(11) 1.4010(9) 0.3649(2) 0.023(2) Uani 1 1 d . . . C22 C 0.2628(11) 1.4107(10) 0.3418(2) 0.029(2) Uani 1 1 d . . . C23 C 0.3781(12) 1.5011(10) 0.3428(2) 0.030(2) Uani 1 1 d . . . C24 C 0.4004(11) 1.5869(10) 0.3665(2) 0.030(2) Uani 1 1 d . . . C25 C 0.3017(11) 1.5817(10) 0.3896(2) 0.025(2) Uani 1 1 d . . . C26 C 0.1844(12) 1.4909(10) 0.3892(2) 0.029(2) Uani 1 1 d . . . C31 C -0.2220(12) 0.9314(9) 0.3425(2) 0.029(2) Uani 1 1 d . . . C32 C -0.1473(12) 0.8095(10) 0.3423(2) 0.031(2) Uani 1 1 d . . . C33 C -0.1600(13) 0.7303(9) 0.3173(2) 0.032(2) Uani 1 1 d . . . C34 C -0.2487(12) 0.7659(9) 0.2918(2) 0.027(2) Uani 1 1 d . . . C35 C -0.3248(11) 0.8855(10) 0.2912(2) 0.028(2) Uani 1 1 d . . . C36 C -0.3070(12) 0.9656(9) 0.3162(2) 0.028(2) Uani 1 1 d . . . C102 C 0.2417(13) 0.8963(11) 0.3286(3) 0.041(3) Uani 1 1 d . . . H10A H 0.3028 0.8735 0.3459 0.049 Uiso 1 1 calc R . . C103 C 0.2557(15) 0.8288(12) 0.3030(3) 0.048(3) Uani 1 1 d . . . H10B H 0.3269 0.7626 0.3027 0.058 Uiso 1 1 calc R . . C104 C 0.1644(14) 0.8580(12) 0.2774(3) 0.044(3) Uani 1 1 d . . . C105 C 0.0636(13) 0.9582(11) 0.2786(3) 0.038(3) Uani 1 1 d . . . H10C H -0.0009 0.9807 0.2618 0.045 Uiso 1 1 calc R . . C106 C 0.0607(12) 1.0242(10) 0.3053(2) 0.028(2) Uani 1 1 d . . . H10D H -0.0046 1.0947 0.3056 0.034 Uiso 1 1 calc R . . C107 C 0.1754(18) 0.7801(13) 0.2485(3) 0.068(4) Uani 1 1 d . . . H10E H 0.1041 0.8133 0.2330 0.102 Uiso 1 1 calc R . . H10F H 0.1521 0.6915 0.2523 0.102 Uiso 1 1 calc R . . H10G H 0.2771 0.7863 0.2422 0.102 Uiso 1 1 calc R . . C202 C 0.3499(11) 1.2724(9) 0.4345(2) 0.026(2) Uani 1 1 d . . . H20A H 0.2760 1.2599 0.4481 0.032 Uiso 1 1 calc R . . C203 C 0.4624(12) 1.3584(10) 0.4423(2) 0.031(2) Uani 1 1 d . . . H20B H 0.4643 1.4034 0.4604 0.037 Uiso 1 1 calc R . . C204 C 0.5759(12) 1.3778(10) 0.4222(2) 0.031(2) Uani 1 1 d . . . C205 C 0.5657(12) 1.3062(10) 0.3965(2) 0.031(2) Uani 1 1 d . . . H20C H 0.6403 1.3154 0.3829 0.038 Uiso 1 1 calc R . . C206 C 0.4498(12) 1.2217(9) 0.3901(2) 0.029(2) Uani 1 1 d . . . H20D H 0.4476 1.1743 0.3723 0.034 Uiso 1 1 calc R . . C207 C 0.7000(13) 1.4748(12) 0.4311(3) 0.049(3) Uani 1 1 d . . . H20E H 0.7697 1.4793 0.4156 0.074 Uiso 1 1 calc R . . H20F H 0.7541 1.4487 0.4497 0.074 Uiso 1 1 calc R . . H20G H 0.6549 1.5579 0.4336 0.074 Uiso 1 1 calc R . . S1 S -0.0338(3) 1.1553(2) 0.43846(5) 0.0242(5) Uani 1 1 d . . . S3 S 0.0052(3) 1.2973(3) 0.36247(6) 0.0315(6) Uani 1 1 d . . . S2 S -0.2098(3) 1.0281(3) 0.37470(6) 0.0309(6) Uani 1 1 d . . . N1 N 0.1429(11) 0.9959(9) 0.3305(2) 0.038(2) Uani 1 1 d . . . N2 N 0.3364(9) 1.2042(7) 0.40895(16) 0.0242(18) Uani 1 1 d . . . Cl12 Cl -0.3632(3) 1.0545(2) 0.45009(6) 0.0335(6) Uani 1 1 d . . . Cl13 Cl -0.4120(3) 0.7947(2) 0.48149(6) 0.0322(6) Uani 1 1 d . . . Cl14 Cl -0.1347(3) 0.6201(2) 0.50125(6) 0.0304(6) Uani 1 1 d . . . Cl15 Cl 0.1939(3) 0.7105(2) 0.49142(6) 0.0317(6) Uani 1 1 d . . . Cl16 Cl 0.2470(3) 0.9690(2) 0.45928(5) 0.0273(5) Uani 1 1 d . . . Cl22 Cl 0.2391(4) 1.3098(3) 0.31110(6) 0.0438(7) Uani 1 1 d . . . Cl23 Cl 0.5080(4) 1.5010(3) 0.31513(6) 0.0470(8) Uani 1 1 d . . . Cl24 Cl 0.5458(3) 1.6971(3) 0.36772(6) 0.0448(7) Uani 1 1 d . . . Cl25 Cl 0.3239(3) 1.6927(3) 0.41841(6) 0.0457(7) Uani 1 1 d . . . Cl26 Cl 0.0730(3) 1.4854(3) 0.41848(6) 0.0381(7) Uani 1 1 d . . . Cl32 Cl -0.0395(3) 0.7570(3) 0.37423(6) 0.0425(7) Uani 1 1 d . . . Cl33 Cl -0.0687(4) 0.5831(3) 0.31745(7) 0.0524(8) Uani 1 1 d . . . Cl34 Cl -0.2696(4) 0.6686(3) 0.26027(6) 0.0474(8) Uani 1 1 d . . . Cl35 Cl -0.4270(4) 0.9364(3) 0.25876(6) 0.0471(8) Uani 1 1 d . . . Cl36 Cl -0.3995(4) 1.1126(3) 0.31485(6) 0.0428(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0285(2) 0.0246(2) 0.0235(2) 0.00250(19) 0.00295(14) -0.0038(2) C11 0.026(5) 0.014(4) 0.017(5) -0.001(4) 0.004(4) -0.003(4) C12 0.032(6) 0.021(5) 0.015(5) 0.001(4) 0.002(4) 0.003(4) C13 0.025(6) 0.025(5) 0.022(5) 0.005(4) 0.006(4) -0.007(4) C14 0.026(6) 0.016(5) 0.018(5) 0.006(4) -0.002(4) -0.003(4) C15 0.018(5) 0.023(5) 0.032(5) -0.010(4) 0.006(4) 0.005(4) C16 0.010(4) 0.026(5) 0.020(4) 0.000(4) -0.001(3) -0.002(4) C21 0.025(5) 0.019(5) 0.026(5) 0.012(4) 0.008(4) 0.003(4) C22 0.033(6) 0.026(5) 0.030(5) 0.000(5) 0.008(4) -0.003(5) C23 0.030(6) 0.031(6) 0.030(6) 0.014(5) 0.007(5) 0.002(5) C24 0.026(5) 0.030(5) 0.033(5) 0.001(5) 0.004(4) -0.001(5) C25 0.029(5) 0.025(5) 0.022(5) -0.001(5) 0.002(4) -0.001(5) C26 0.027(6) 0.033(6) 0.027(5) 0.009(5) 0.011(4) 0.015(5) C31 0.036(6) 0.023(5) 0.029(5) 0.003(5) 0.007(4) -0.007(5) C32 0.035(6) 0.023(5) 0.034(6) 0.005(5) -0.001(5) -0.006(5) C33 0.038(7) 0.017(5) 0.039(6) 0.000(5) 0.004(5) -0.003(5) C34 0.028(6) 0.022(5) 0.034(6) -0.005(4) 0.013(5) -0.007(4) C35 0.027(6) 0.036(6) 0.020(5) 0.005(4) 0.006(4) -0.004(5) C36 0.026(6) 0.019(5) 0.039(6) 0.013(4) 0.004(5) 0.005(4) C102 0.042(7) 0.037(7) 0.044(7) 0.004(6) 0.002(5) -0.003(6) C103 0.060(9) 0.038(7) 0.050(8) 0.002(6) 0.023(7) 0.019(6) C104 0.043(7) 0.047(7) 0.043(7) -0.012(6) 0.016(6) -0.015(6) C105 0.030(6) 0.045(7) 0.039(7) 0.004(5) 0.008(5) -0.005(5) C106 0.027(6) 0.028(5) 0.031(6) 0.002(5) 0.013(5) -0.004(5) C107 0.094(12) 0.050(9) 0.063(9) -0.019(7) 0.024(8) -0.002(8) C202 0.019(5) 0.032(6) 0.028(6) 0.008(5) 0.004(4) -0.009(4) C203 0.036(6) 0.033(6) 0.023(5) 0.007(5) -0.002(5) 0.003(5) C204 0.022(6) 0.024(5) 0.047(7) 0.010(5) 0.002(5) 0.004(4) C205 0.025(6) 0.035(6) 0.035(6) 0.013(5) 0.009(5) 0.008(5) C206 0.036(6) 0.020(5) 0.031(6) 0.006(4) 0.005(5) 0.000(5) C207 0.030(7) 0.044(7) 0.074(9) 0.015(7) -0.001(6) -0.002(6) S1 0.0281(14) 0.0208(12) 0.0245(13) 0.0045(10) 0.0060(10) 0.0009(11) S3 0.0268(15) 0.0295(14) 0.0382(15) 0.0102(12) 0.0036(12) -0.0054(12) S2 0.0273(15) 0.0361(14) 0.0293(14) -0.0023(12) 0.0025(11) -0.0033(12) N1 0.045(6) 0.036(5) 0.034(5) 0.003(4) 0.017(5) -0.004(5) N2 0.032(5) 0.022(4) 0.020(4) 0.005(3) 0.005(4) 0.000(4) Cl12 0.0239(13) 0.0299(14) 0.0471(15) 0.0154(11) 0.0047(11) 0.0071(11) Cl13 0.0196(13) 0.0338(14) 0.0438(15) 0.0099(12) 0.0052(11) -0.0065(11) Cl14 0.0306(14) 0.0186(12) 0.0425(15) 0.0068(10) 0.0061(11) -0.0015(10) Cl15 0.0266(14) 0.0301(13) 0.0388(14) 0.0111(11) 0.0055(11) 0.0081(11) Cl16 0.0194(13) 0.0299(13) 0.0332(13) 0.0044(11) 0.0053(10) -0.0026(10) Cl22 0.0548(19) 0.0398(16) 0.0381(16) -0.0097(13) 0.0117(14) -0.0125(15) Cl23 0.0472(19) 0.0563(19) 0.0401(16) -0.0046(14) 0.0198(14) -0.0162(16) Cl24 0.0393(17) 0.0456(17) 0.0499(18) 0.0012(14) 0.0064(14) -0.0179(14) Cl25 0.0475(19) 0.0499(18) 0.0403(16) -0.0134(14) 0.0054(14) -0.0068(15) Cl26 0.0379(16) 0.0429(16) 0.0355(15) 0.0041(12) 0.0150(12) 0.0013(13) Cl32 0.0418(18) 0.0409(16) 0.0435(16) 0.0118(13) -0.0044(13) 0.0034(14) Cl33 0.058(2) 0.0315(15) 0.068(2) -0.0003(16) 0.0022(16) 0.0146(16) Cl34 0.062(2) 0.0438(17) 0.0370(16) -0.0094(13) 0.0090(14) -0.0031(16) Cl35 0.0536(19) 0.056(2) 0.0306(14) 0.0009(14) -0.0063(13) 0.0089(16) Cl36 0.0537(19) 0.0357(16) 0.0394(15) 0.0029(12) 0.0050(13) 0.0191(14) _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 S3 2.580(3) . ? Bi1 S1 2.619(2) . ? Bi1 S2 2.654(3) . ? Bi1 N2 2.660(8) . ? C11 C12 1.393(13) . ? C11 C16 1.410(12) . ? C11 S1 1.778(9) . ? C12 C13 1.400(13) . ? C12 Cl12 1.730(10) . ? C13 C14 1.368(13) . ? C13 Cl13 1.720(10) . ? C14 C15 1.425(13) . ? C14 Cl14 1.707(9) . ? C15 C16 1.396(13) . ? C15 Cl15 1.712(10) . ? C16 Cl16 1.718(9) . ? C21 C22 1.416(13) . ? C21 C26 1.426(14) . ? C21 S3 1.743(10) . ? C22 C23 1.380(14) . ? C22 Cl22 1.717(10) . ? C23 C24 1.380(14) . ? C23 Cl23 1.743(10) . ? C24 C25 1.395(13) . ? C24 Cl24 1.713(10) . ? C25 C26 1.396(14) . ? C25 Cl25 1.722(10) . ? C26 Cl26 1.691(10) . ? C31 C36 1.380(13) . ? C31 C32 1.427(14) . ? C31 S2 1.744(10) . ? C32 C33 1.376(14) . ? C32 Cl32 1.732(10) . ? C33 C34 1.375(14) . ? C33 Cl33 1.726(10) . ? C34 C35 1.410(14) . ? C34 Cl34 1.724(10) . ? C35 C36 1.386(14) . ? C35 Cl35 1.721(10) . ? C36 Cl36 1.728(10) . ? C102 N1 1.357(14) . ? C102 C103 1.350(15) . ? C103 C104 1.375(16) . ? C104 C105 1.370(16) . ? C104 C107 1.524(16) . ? C105 C106 1.372(14) . ? C106 N1 1.317(13) . ? C202 N2 1.336(12) . ? C202 C203 1.357(14) . ? C203 C204 1.403(14) . ? C204 C205 1.362(14) . ? C204 C207 1.514(15) . ? C205 C206 1.356(14) . ? C206 N2 1.363(12) . ? 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 S3 Bi1 S1 91.48(8) . . ? S3 Bi1 S2 82.19(8) . . ? S1 Bi1 S2 79.90(8) . . ? S3 Bi1 N2 85.77(17) . . ? S1 Bi1 N2 87.14(17) . . ? S2 Bi1 N2 162.03(18) . . ? C12 C11 C16 117.4(8) . . ? C12 C11 S1 120.7(7) . . ? C16 C11 S1 121.8(7) . . ? C11 C12 C13 121.9(9) . . ? C11 C12 Cl12 119.7(7) . . ? C13 C12 Cl12 118.3(8) . . ? C14 C13 C12 120.4(9) . . ? C14 C13 Cl13 119.5(7) . . ? C12 C13 Cl13 120.1(8) . . ? C13 C14 C15 119.5(8) . . ? C13 C14 Cl14 121.5(7) . . ? C15 C14 Cl14 119.0(7) . . ? C16 C15 C14 119.4(8) . . ? C16 C15 Cl15 121.0(7) . . ? C14 C15 Cl15 119.6(7) . . ? C15 C16 C11 121.3(8) . . ? C15 C16 Cl16 118.3(7) . . ? C11 C16 Cl16 120.3(7) . . ? C22 C21 C26 116.3(9) . . ? C22 C21 S3 122.4(8) . . ? C26 C21 S3 121.0(7) . . ? C23 C22 C21 121.6(9) . . ? C23 C22 Cl22 119.0(8) . . ? C21 C22 Cl22 119.3(8) . . ? C22 C23 C24 121.7(9) . . ? C22 C23 Cl23 119.7(8) . . ? C24 C23 Cl23 118.5(8) . . ? C23 C24 C25 118.4(10) . . ? C23 C24 Cl24 121.1(8) . . ? C25 C24 Cl24 120.5(8) . . ? C24 C25 C26 121.1(9) . . ? C24 C25 Cl25 118.7(8) . . ? C26 C25 Cl25 120.1(7) . . ? C25 C26 C21 120.8(8) . . ? C25 C26 Cl26 119.0(8) . . ? C21 C26 Cl26 120.2(8) . . ? C36 C31 C32 116.1(9) . . ? C36 C31 S2 122.6(8) . . ? C32 C31 S2 121.2(8) . . ? C33 C32 C31 121.8(9) . . ? C33 C32 Cl32 118.4(8) . . ? C31 C32 Cl32 119.7(8) . . ? C34 C33 C32 120.5(10) . . ? C34 C33 Cl33 118.2(8) . . ? C32 C33 Cl33 121.2(8) . . ? C33 C34 C35 119.2(9) . . ? C33 C34 Cl34 122.0(8) . . ? C35 C34 Cl34 118.8(8) . . ? C36 C35 C34 119.4(9) . . ? C36 C35 Cl35 120.4(8) . . ? C34 C35 Cl35 120.0(8) . . ? C31 C36 C35 122.8(9) . . ? C31 C36 Cl36 118.6(8) . . ? C35 C36 Cl36 118.6(8) . . ? N1 C102 C103 123.2(11) . . ? C102 C103 C104 119.8(12) . . ? C105 C104 C103 118.2(11) . . ? C105 C104 C107 121.3(12) . . ? C103 C104 C107 120.5(12) . . ? C104 C105 C106 118.0(11) . . ? N1 C106 C105 125.2(11) . . ? N2 C202 C203 125.4(9) . . ? C202 C203 C204 118.2(10) . . ? C205 C204 C203 117.0(10) . . ? C205 C204 C207 125.4(10) . . ? C203 C204 C207 117.6(10) . . ? C204 C205 C206 121.7(10) . . ? N2 C206 C205 122.1(10) . . ? C11 S1 Bi1 99.4(3) . . ? C21 S3 Bi1 109.1(3) . . ? C31 S2 Bi1 108.1(4) . . ? C106 N1 C102 115.5(9) . . ? C202 N2 C206 115.5(9) . . ? C202 N2 Bi1 123.7(6) . . ? C206 N2 Bi1 119.4(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.463 _refine_diff_density_min -2.138 _refine_diff_density_rms 0.218 #===END data_8 _database_code_CSD 211639 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H8 Bi F15 N2 S3' _chemical_formula_sum 'C28 H8 Bi F15 N2 S3' _chemical_formula_weight 962.52 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6388(15) _cell_length_b 12.2386(15) _cell_length_c 13.241(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.083(13) _cell_angle_gamma 90.00 _cell_volume 1457.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 147 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 6.386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.340 _exptl_absorpt_correction_T_max 0.530 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD area detector' _diffrn_measurement_method '\w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9460 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.1041 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5281 _reflns_number_gt 4028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0181P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.035(6) _refine_ls_number_reflns 5281 _refine_ls_number_parameters 443 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 0.824 _refine_ls_restrained_S_all 0.824 _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 -0.26215(3) -0.05195(3) 0.42029(2) 0.02544(7) Uani 1 1 d . . . N1 N -0.4429(7) -0.0683(6) 0.5261(5) 0.0231(19) Uani 1 1 d . . . N2 N -0.2008(7) 0.0636(6) 0.5931(6) 0.0287(17) Uani 1 1 d . . . C1 C -0.5635(10) -0.1294(7) 0.4857(7) 0.034(2) Uani 1 1 d . . . H1A H -0.5758 -0.1720 0.4231 0.041 Uiso 1 1 calc R . . C2 C -0.6714(10) -0.1340(7) 0.5303(7) 0.037(2) Uani 1 1 d . . . H2A H -0.7555 -0.1804 0.5012 0.044 Uiso 1 1 calc R . . C3 C -0.6533(10) -0.0684(10) 0.6194(7) 0.040(3) Uani 1 1 d . . . H3A H -0.7257 -0.0696 0.6527 0.048 Uiso 1 1 calc R . . C4 C -0.5316(10) -0.0019(6) 0.6597(6) 0.030(2) Uani 1 1 d . . . H4A H -0.5203 0.0445 0.7197 0.036 Uiso 1 1 calc R . . C5 C -0.4255(9) -0.0031(6) 0.6121(6) 0.0242(19) Uani 1 1 d . . . C6 C -0.2911(9) 0.0690(6) 0.6495(6) 0.0270(19) Uani 1 1 d . . . C7 C -0.2622(11) 0.1377(7) 0.7386(7) 0.038(2) Uani 1 1 d . . . H7A H -0.3288 0.1422 0.7767 0.045 Uiso 1 1 calc R . . C8 C -0.1321(11) 0.1998(7) 0.7699(7) 0.045(3) Uani 1 1 d . . . H8A H -0.1084 0.2462 0.8314 0.054 Uiso 1 1 calc R . . C9 C -0.0371(10) 0.1948(7) 0.7124(7) 0.039(2) Uani 1 1 d . . . H9A H 0.0508 0.2378 0.7332 0.047 Uiso 1 1 calc R . . C10 C -0.0729(10) 0.1264(7) 0.6249(7) 0.033(2) Uani 1 1 d . . . H10A H -0.0084 0.1219 0.5851 0.040 Uiso 1 1 calc R . . S1 S -0.0081(2) -0.00292(17) 0.39278(17) 0.0326(5) Uani 1 1 d . . . C11 C -0.0855(9) 0.0716(6) 0.2714(6) 0.0258(19) Uani 1 1 d . . . C12 C -0.0452(9) 0.0508(6) 0.1820(7) 0.028(2) Uani 1 1 d . . . F12 F 0.0611(5) -0.0264(5) 0.1919(4) 0.0445(17) Uani 1 1 d . . . C13 C -0.0988(10) 0.1086(7) 0.0887(7) 0.034(2) Uani 1 1 d . . . F13 F -0.0539(6) 0.0867(4) 0.0060(4) 0.0510(15) Uani 1 1 d . . . C14 C -0.2068(9) 0.1872(7) 0.0746(7) 0.030(2) Uani 1 1 d . . . F14 F -0.2631(6) 0.2399(5) -0.0190(4) 0.0549(16) Uani 1 1 d . . . C15 C -0.2519(10) 0.2082(6) 0.1584(7) 0.035(2) Uani 1 1 d . . . F15 F -0.3553(6) 0.2860(4) 0.1488(4) 0.0498(16) Uani 1 1 d . . . C16 C -0.1909(9) 0.1534(6) 0.2561(7) 0.028(2) Uani 1 1 d . . . F16 F -0.2398(6) 0.1790(4) 0.3366(4) 0.0378(13) Uani 1 1 d . . . S2 S -0.3520(3) -0.21791(17) 0.27997(17) 0.0331(5) Uani 1 1 d . . . C21 C -0.4311(9) -0.1311(6) 0.1673(6) 0.028(2) Uani 1 1 d . . . C22 C -0.5691(10) -0.0804(6) 0.1465(7) 0.032(2) Uani 1 1 d . . . F22 F -0.6450(5) -0.0984(4) 0.2123(4) 0.0463(14) Uani 1 1 d . . . C23 C -0.6372(10) -0.0160(7) 0.0573(7) 0.039(3) Uani 1 1 d . . . F23 F -0.7728(6) 0.0240(4) 0.0367(4) 0.0551(15) Uani 1 1 d . . . C24 C -0.5658(11) 0.0017(7) -0.0146(7) 0.039(2) Uani 1 1 d . . . F24 F -0.6278(7) 0.0642(5) -0.1035(4) 0.0542(17) Uani 1 1 d . . . C25 C -0.4255(9) -0.0439(14) 0.0048(6) 0.0358(18) Uani 1 1 d . . . F25 F -0.3582(6) -0.0259(4) -0.0667(3) 0.0448(17) Uani 1 1 d . . . C26 C -0.3637(9) -0.1088(7) 0.0930(6) 0.0284(19) Uani 1 1 d . . . F26 F -0.2316(6) -0.1550(4) 0.1079(3) 0.0425(13) Uani 1 1 d . . . S3 S -0.0866(3) -0.19117(18) 0.54733(19) 0.0379(6) Uani 1 1 d . . . C31 C -0.1581(11) -0.2121(7) 0.6518(7) 0.033(2) Uani 1 1 d . . . C32 C -0.2771(10) -0.2805(7) 0.6376(7) 0.034(2) Uani 1 1 d . . . F32 F -0.3474(6) -0.3307(4) 0.5410(4) 0.0463(14) Uani 1 1 d . . . C33 C -0.3321(11) -0.2995(8) 0.7200(9) 0.042(3) Uani 1 1 d . . . F33 F -0.4504(6) -0.3644(4) 0.7024(5) 0.0619(16) Uani 1 1 d . . . C34 C -0.2690(11) -0.2490(8) 0.8161(8) 0.038(2) Uani 1 1 d . . . F34 F -0.3210(7) -0.2651(5) 0.8952(5) 0.0628(18) Uani 1 1 d . . . C35 C -0.1479(10) -0.1821(7) 0.8337(7) 0.034(2) Uani 1 1 d . . . F35 F -0.0777(6) -0.1373(5) 0.9324(4) 0.0527(15) Uani 1 1 d . . . C36 C -0.0952(10) -0.1645(7) 0.7518(7) 0.032(2) Uani 1 1 d . . . F36 F 0.0248(5) -0.0989(3) 0.7726(4) 0.0374(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.02639(14) 0.02613(12) 0.02457(13) -0.0006(3) 0.01010(10) 0.0011(3) N1 0.029(4) 0.012(6) 0.028(3) 0.002(3) 0.011(3) 0.003(3) N2 0.024(5) 0.036(4) 0.032(4) -0.006(3) 0.016(4) -0.005(3) C1 0.036(6) 0.034(5) 0.026(5) 0.006(4) 0.003(4) -0.005(4) C2 0.030(6) 0.034(5) 0.036(5) 0.007(4) 0.001(5) -0.004(4) C3 0.032(5) 0.047(9) 0.043(5) 0.012(5) 0.015(4) -0.001(5) C4 0.035(6) 0.032(5) 0.023(5) 0.008(4) 0.012(4) 0.004(4) C5 0.022(5) 0.026(4) 0.022(4) 0.013(3) 0.004(4) 0.013(3) C6 0.027(5) 0.033(5) 0.021(5) 0.004(4) 0.009(4) 0.005(4) C7 0.040(6) 0.045(6) 0.033(6) -0.009(5) 0.020(5) -0.007(5) C8 0.071(8) 0.040(6) 0.031(5) -0.015(4) 0.027(6) -0.024(5) C9 0.037(6) 0.032(5) 0.040(6) -0.013(4) 0.005(5) -0.015(4) C10 0.025(6) 0.042(6) 0.040(6) 0.006(4) 0.021(5) 0.001(4) S1 0.0261(13) 0.0361(12) 0.0343(13) 0.0056(9) 0.0094(11) 0.0036(9) C11 0.017(5) 0.025(4) 0.033(5) 0.008(4) 0.005(4) 0.000(3) C12 0.019(5) 0.025(5) 0.038(5) 0.003(4) 0.010(4) 0.007(3) F12 0.046(3) 0.041(5) 0.055(3) 0.009(3) 0.029(3) 0.017(3) C13 0.028(5) 0.039(5) 0.044(6) 0.006(4) 0.022(5) 0.000(4) F13 0.053(4) 0.064(4) 0.045(3) 0.005(3) 0.028(3) 0.018(3) C14 0.029(6) 0.029(5) 0.040(5) 0.006(4) 0.020(5) 0.006(4) F14 0.059(4) 0.060(4) 0.047(3) 0.027(3) 0.022(3) 0.018(3) C15 0.031(6) 0.023(5) 0.054(6) 0.002(4) 0.020(5) 0.010(4) F15 0.050(4) 0.046(4) 0.060(4) 0.017(3) 0.027(3) 0.024(3) C16 0.020(5) 0.029(5) 0.039(5) 0.000(4) 0.016(4) 0.002(4) F16 0.036(3) 0.039(3) 0.045(3) -0.005(2) 0.022(3) 0.006(2) S2 0.0411(15) 0.0279(12) 0.0285(13) -0.0033(10) 0.0103(11) -0.0038(10) C21 0.026(5) 0.028(5) 0.028(5) -0.013(4) 0.006(4) -0.003(4) C22 0.031(5) 0.028(6) 0.035(5) -0.010(4) 0.010(4) -0.010(3) F22 0.034(3) 0.055(3) 0.062(4) 0.007(2) 0.031(3) 0.004(2) C23 0.030(6) 0.044(7) 0.047(6) -0.004(4) 0.019(5) 0.000(4) F23 0.036(4) 0.058(4) 0.067(4) 0.008(3) 0.013(3) 0.010(3) C24 0.042(6) 0.031(5) 0.035(5) 0.003(4) 0.004(5) 0.003(4) F24 0.058(4) 0.057(4) 0.045(4) 0.015(3) 0.015(3) 0.011(3) C25 0.036(5) 0.040(5) 0.037(4) 0.003(8) 0.021(4) 0.012(8) F25 0.061(3) 0.039(5) 0.044(3) 0.011(2) 0.029(3) 0.006(3) C26 0.021(5) 0.038(5) 0.029(5) -0.007(4) 0.013(4) 0.000(4) F26 0.043(3) 0.054(3) 0.033(3) 0.005(2) 0.016(3) 0.007(3) S3 0.0424(16) 0.0381(14) 0.0376(14) 0.0107(11) 0.0196(13) 0.0140(11) C31 0.046(7) 0.024(5) 0.026(5) 0.007(4) 0.010(5) -0.001(4) C32 0.027(6) 0.033(5) 0.037(6) 0.000(4) 0.005(5) 0.006(4) F32 0.042(4) 0.042(3) 0.043(3) -0.009(2) 0.002(3) -0.001(2) C33 0.036(7) 0.035(6) 0.064(8) 0.012(5) 0.026(6) -0.003(5) F33 0.045(4) 0.054(4) 0.089(4) 0.016(3) 0.027(3) -0.007(3) C34 0.037(6) 0.035(6) 0.047(6) 0.006(5) 0.022(5) 0.007(4) F34 0.072(5) 0.070(4) 0.065(4) 0.013(3) 0.048(4) 0.000(3) C35 0.034(6) 0.036(5) 0.029(5) 0.011(4) 0.009(5) 0.005(4) F35 0.062(4) 0.061(4) 0.032(3) -0.010(3) 0.014(3) 0.002(3) C36 0.031(6) 0.033(5) 0.035(5) 0.010(4) 0.018(5) -0.002(4) F36 0.028(3) 0.035(3) 0.043(3) 0.002(2) 0.005(3) -0.006(2) _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 S3 2.559(2) . ? Bi1 N2 2.572(7) . ? Bi1 N1 2.607(6) . ? Bi1 S1 2.670(2) . ? Bi1 S2 2.678(2) . ? N1 C1 1.323(10) . ? N1 C5 1.350(9) . ? N2 C6 1.336(10) . ? N2 C10 1.384(10) . ? C1 C2 1.369(11) . ? C2 C3 1.385(12) . ? C3 C4 1.369(12) . ? C4 C5 1.381(11) . ? C5 C6 1.497(11) . ? C6 C7 1.393(11) . ? C7 C8 1.395(12) . ? C8 C9 1.388(11) . ? C9 C10 1.369(11) . ? S1 C11 1.763(8) . ? C11 C16 1.389(10) . ? C11 C12 1.396(11) . ? C12 C13 1.355(11) . ? C12 F12 1.365(9) . ? C13 F13 1.341(9) . ? C13 C14 1.380(11) . ? C14 F14 1.328(9) . ? C14 C15 1.353(11) . ? C15 F15 1.352(9) . ? C15 C16 1.386(11) . ? C16 F16 1.348(9) . ? S2 C21 1.765(8) . ? C21 C26 1.387(10) . ? C21 C22 1.402(11) . ? C22 F22 1.342(9) . ? C22 C23 1.374(10) . ? C23 F23 1.329(10) . ? C23 C24 1.378(12) . ? C24 F24 1.350(9) . ? C24 C25 1.399(12) . ? C25 F25 1.345(8) . ? C25 C26 1.359(13) . ? C26 F26 1.342(9) . ? S3 C31 1.772(9) . ? C31 C36 1.372(11) . ? C31 C32 1.377(12) . ? C32 F32 1.360(9) . ? C32 C33 1.393(12) . ? C33 F33 1.339(10) . ? C33 C34 1.347(13) . ? C34 F34 1.329(10) . ? C34 C35 1.375(12) . ? C35 F35 1.353(9) . ? C35 C36 1.370(11) . ? C36 F36 1.353(9) . ? 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 S3 Bi1 N2 84.00(16) . . ? S3 Bi1 N1 90.43(15) . . ? N2 Bi1 N1 63.1(2) . . ? S3 Bi1 S1 79.47(7) . . ? N2 Bi1 S1 93.97(15) . . ? N1 Bi1 S1 156.00(15) . . ? S3 Bi1 S2 85.61(8) . . ? N2 Bi1 S2 161.47(15) . . ? N1 Bi1 S2 101.72(16) . . ? S1 Bi1 S2 99.17(7) . . ? C1 N1 C5 120.0(7) . . ? C1 N1 Bi1 119.1(5) . . ? C5 N1 Bi1 120.2(5) . . ? C6 N2 C10 119.4(8) . . ? C6 N2 Bi1 122.4(5) . . ? C10 N2 Bi1 118.1(5) . . ? N1 C1 C2 122.8(8) . . ? C1 C2 C3 117.5(8) . . ? C4 C3 C2 120.3(8) . . ? C3 C4 C5 119.2(8) . . ? N1 C5 C4 120.2(8) . . ? N1 C5 C6 117.2(7) . . ? C4 C5 C6 122.5(7) . . ? N2 C6 C7 122.0(8) . . ? N2 C6 C5 116.5(7) . . ? C7 C6 C5 121.4(7) . . ? C6 C7 C8 117.7(8) . . ? C9 C8 C7 120.9(8) . . ? C10 C9 C8 118.4(8) . . ? C9 C10 N2 121.5(8) . . ? C11 S1 Bi1 97.6(3) . . ? C16 C11 C12 114.8(7) . . ? C16 C11 S1 123.6(6) . . ? C12 C11 S1 121.5(6) . . ? C13 C12 F12 118.4(7) . . ? C13 C12 C11 123.2(7) . . ? F12 C12 C11 118.2(7) . . ? F13 C13 C12 120.7(8) . . ? F13 C13 C14 118.6(8) . . ? C12 C13 C14 120.6(8) . . ? F14 C14 C15 122.0(8) . . ? F14 C14 C13 120.0(7) . . ? C15 C14 C13 118.1(8) . . ? F15 C15 C14 120.0(8) . . ? F15 C15 C16 118.6(8) . . ? C14 C15 C16 121.4(8) . . ? F16 C16 C15 118.3(7) . . ? F16 C16 C11 119.9(7) . . ? C15 C16 C11 121.8(8) . . ? C21 S2 Bi1 93.6(3) . . ? C26 C21 C22 115.3(8) . . ? C26 C21 S2 123.2(7) . . ? C22 C21 S2 121.5(6) . . ? F22 C22 C23 116.7(8) . . ? F22 C22 C21 120.0(7) . . ? C23 C22 C21 123.3(8) . . ? F23 C23 C22 121.2(8) . . ? F23 C23 C24 119.9(8) . . ? C22 C23 C24 118.8(9) . . ? F24 C24 C23 121.2(8) . . ? F24 C24 C25 118.8(8) . . ? C23 C24 C25 120.0(8) . . ? F25 C25 C26 121.8(8) . . ? F25 C25 C24 119.0(9) . . ? C26 C25 C24 119.1(7) . . ? F26 C26 C25 118.1(7) . . ? F26 C26 C21 118.4(7) . . ? C25 C26 C21 123.5(8) . . ? C31 S3 Bi1 105.0(3) . . ? C36 C31 C32 116.5(8) . . ? C36 C31 S3 122.0(7) . . ? C32 C31 S3 121.4(7) . . ? F32 C32 C31 120.7(8) . . ? F32 C32 C33 117.3(8) . . ? C31 C32 C33 121.9(9) . . ? F33 C33 C34 120.2(9) . . ? F33 C33 C32 120.3(9) . . ? C34 C33 C32 119.5(9) . . ? F34 C34 C33 120.5(9) . . ? F34 C34 C35 119.5(9) . . ? C33 C34 C35 120.0(9) . . ? F35 C35 C36 120.1(8) . . ? F35 C35 C34 120.2(8) . . ? C36 C35 C34 119.6(9) . . ? F36 C36 C35 117.8(8) . . ? F36 C36 C31 119.8(7) . . ? C35 C36 C31 122.4(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.344 _refine_diff_density_min -0.982 _refine_diff_density_rms 0.125 #===END data_9 _database_code_CSD 211640 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 Bi Cl15 S3, C10 H8 N2' _chemical_formula_sum 'C28 H8 Bi Cl15 N2 S3' _chemical_formula_weight 1209.27 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.437(3) _cell_length_b 14.708(4) _cell_length_c 26.464(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.530(6) _cell_angle_gamma 90.00 _cell_volume 3641.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 828 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 21.51 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 6.143 _exptl_absorpt_correction_type mult-scan _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1998)' _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 31075 _diffrn_reflns_av_R_equivalents 0.1425 _diffrn_reflns_av_sigmaI/netI 0.1273 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6413 _reflns_number_gt 3679 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Brucker SMART' _computing_cell_refinement 'Brucker SMART' _computing_data_reduction 'Brucker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.1038P)^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 SHELXL _refine_ls_extinction_coef 0.0020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6413 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1276 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1820 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 0.07128(6) 0.13779(4) 0.18875(2) 0.0306(2) Uani 1 1 d . . . S1 S 0.3255(4) 0.2111(3) 0.19355(14) 0.0329(9) Uani 1 1 d . . . S3 S 0.2106(4) 0.0154(3) 0.24420(14) 0.0344(9) Uani 1 1 d . . . S2 S 0.1162(4) 0.0296(3) 0.11007(14) 0.0371(9) Uani 1 1 d . . . C1 C 0.1442(10) 0.2882(8) 0.2924(4) 0.067(6) Uani 1 1 d G . . H1A H 0.2142 0.3020 0.2719 0.080 Uiso 1 1 calc R . . C2 C 0.1456(12) 0.3307(7) 0.3394(5) 0.106(10) Uani 1 1 d G . . H2A H 0.2165 0.3728 0.3503 0.127 Uiso 1 1 calc R . . C3 C 0.0410(14) 0.3101(8) 0.3700(4) 0.092(8) Uani 1 1 d G . . H3A H 0.0419 0.3385 0.4014 0.110 Uiso 1 1 calc R . . C4 C -0.0650(12) 0.2471(8) 0.3536(4) 0.051(5) Uani 1 1 d G . . H4A H -0.1349 0.2334 0.3741 0.061 Uiso 1 1 calc R . . C5 C -0.0663(10) 0.2047(7) 0.3066(4) 0.065(6) Uani 1 1 d G . . N2 N 0.0383(11) 0.2253(7) 0.2760(3) 0.039(3) Uani 1 1 d G . . C6 C -0.1736(10) 0.1423(7) 0.2860(5) 0.061(4) Uani 1 1 d G . . C7 C -0.2933(13) 0.1221(8) 0.3094(4) 0.083(5) Uani 1 1 d G . . H7A H -0.3013 0.1450 0.3417 0.099 Uiso 1 1 calc R . . C8 C -0.4011(10) 0.0676(8) 0.2846(5) 0.059(5) Uani 1 1 d G . . H8A H -0.4812 0.0541 0.3003 0.070 Uiso 1 1 calc R . . C9 C -0.3892(11) 0.0334(7) 0.2364(5) 0.061(4) Uani 1 1 d G . . H9A H -0.4613 -0.0030 0.2198 0.073 Uiso 1 1 calc R . . C10 C -0.2695(14) 0.0536(8) 0.2130(4) 0.083(5) Uani 1 1 d G . . H10A H -0.2615 0.0307 0.1807 0.099 Uiso 1 1 calc R . . N1 N -0.1617(10) 0.1081(8) 0.2378(5) 0.068(5) Uani 1 1 d G . . C11 C 0.3005(14) 0.2590(9) 0.1328(5) 0.025(3) Uani 1 1 d . . . C12 C 0.3816(15) 0.2354(10) 0.0956(6) 0.040(4) Uani 1 1 d . . . C13 C 0.3615(17) 0.2720(11) 0.0454(6) 0.044(4) Uani 1 1 d . . . C14 C 0.2537(17) 0.3384(10) 0.0341(5) 0.037(4) Uani 1 1 d . . . C15 C 0.1698(15) 0.3645(10) 0.0702(6) 0.036(4) Uani 1 1 d . . . C16 C 0.1908(14) 0.3266(9) 0.1181(5) 0.029(3) Uani 1 1 d . . . C21 C 0.0983(14) -0.0163(8) 0.2890(5) 0.024(3) Uani 1 1 d . . . C22 C 0.1187(14) 0.0185(9) 0.3391(5) 0.030(3) Uani 1 1 d . . . C23 C 0.0322(14) -0.0050(9) 0.3753(5) 0.027(3) Uani 1 1 d . . . C24 C -0.0798(15) -0.0673(10) 0.3631(6) 0.036(4) Uani 1 1 d . . . C25 C -0.1001(13) -0.1046(9) 0.3135(6) 0.031(4) Uani 1 1 d . . . C26 C -0.0143(13) -0.0801(9) 0.2776(5) 0.027(3) Uani 1 1 d . . . C31 C 0.0905(15) 0.0864(9) 0.0516(5) 0.030(3) Uani 1 1 d . . . C32 C -0.0162(15) 0.1512(10) 0.0377(5) 0.033(4) Uani 1 1 d . . . C33 C -0.0332(15) 0.1910(9) -0.0113(5) 0.032(3) Uani 1 1 d . . . C34 C 0.0544(17) 0.1677(11) -0.0472(6) 0.040(4) Uani 1 1 d . . . C35 C 0.1585(17) 0.1012(11) -0.0343(6) 0.042(4) Uani 1 1 d . . . C36 C 0.1781(15) 0.0623(10) 0.0137(6) 0.038(4) Uani 1 1 d . . . Cl12 Cl 0.5166(4) 0.1572(3) 0.10977(18) 0.0538(12) Uani 1 1 d . . . Cl13 Cl 0.4707(5) 0.2423(3) 0.00222(17) 0.0593(12) Uani 1 1 d . . . Cl14 Cl 0.2265(5) 0.3834(3) -0.02592(15) 0.0551(12) Uani 1 1 d . . . Cl15 Cl 0.0368(4) 0.4432(3) 0.05548(15) 0.0485(11) Uani 1 1 d . . . Cl16 Cl 0.0861(4) 0.3622(2) 0.16325(14) 0.0368(8) Uani 1 1 d . . . Cl22 Cl 0.2566(4) 0.0944(3) 0.35622(15) 0.0425(10) Uani 1 1 d . . . Cl23 Cl 0.0608(4) 0.0391(3) 0.43544(14) 0.0435(10) Uani 1 1 d . . . Cl24 Cl -0.1886(4) -0.0967(3) 0.40659(16) 0.0495(11) Uani 1 1 d . . . Cl25 Cl -0.2380(4) -0.1811(3) 0.29781(17) 0.0496(11) Uani 1 1 d . . . Cl26 Cl -0.0444(4) -0.1242(3) 0.21704(14) 0.0407(9) Uani 1 1 d . . . Cl32 Cl -0.1280(4) 0.1837(3) 0.08023(14) 0.0392(9) Uani 1 1 d . . . Cl33 Cl -0.1646(5) 0.2719(3) -0.02594(15) 0.0501(11) Uani 1 1 d . . . Cl34 Cl 0.0302(5) 0.2168(3) -0.10630(15) 0.0600(13) Uani 1 1 d . . . Cl35 Cl 0.2639(5) 0.0684(3) -0.07979(17) 0.0625(13) Uani 1 1 d . . . Cl36 Cl 0.3087(4) -0.0188(3) 0.02715(18) 0.0560(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0376(3) 0.0182(3) 0.0371(4) 0.0083(3) 0.0090(2) -0.0012(3) S1 0.040(2) 0.025(2) 0.034(2) 0.0066(16) 0.0068(17) -0.0047(16) S3 0.040(2) 0.026(2) 0.039(2) 0.0129(17) 0.0122(17) 0.0065(16) S2 0.055(2) 0.018(2) 0.037(2) 0.0015(17) 0.0044(18) 0.0062(17) C1 0.135(18) 0.031(11) 0.036(11) 0.003(9) 0.013(11) 0.008(12) C2 0.13(2) 0.073(18) 0.12(2) 0.072(17) 0.063(18) 0.045(15) C3 0.075(14) 0.036(13) 0.16(2) 0.000(14) 0.017(16) 0.026(11) C4 0.080(12) 0.054(12) 0.025(9) -0.027(8) 0.029(8) -0.030(10) C5 0.066(12) 0.037(11) 0.088(15) 0.009(11) -0.008(11) -0.007(10) N2 0.042(7) 0.025(7) 0.058(9) 0.020(7) 0.038(7) 0.012(6) C6 0.066(9) 0.039(8) 0.088(11) 0.015(8) 0.046(8) 0.004(7) C7 0.106(12) 0.041(10) 0.091(12) 0.003(8) -0.024(10) 0.011(8) C8 0.025(8) 0.040(11) 0.110(16) 0.004(11) 0.009(9) -0.020(8) C9 0.066(9) 0.039(8) 0.088(11) 0.015(8) 0.046(8) 0.004(7) C10 0.106(12) 0.041(10) 0.091(12) 0.003(8) -0.024(10) 0.011(8) N1 0.102(13) 0.035(9) 0.071(11) 0.003(8) 0.023(10) 0.034(9) C11 0.032(8) 0.009(7) 0.035(8) -0.001(6) 0.010(6) 0.000(6) C12 0.037(9) 0.029(9) 0.052(10) -0.001(8) 0.001(8) -0.005(7) C13 0.058(11) 0.031(10) 0.045(10) -0.004(8) 0.017(8) -0.015(8) C14 0.057(10) 0.024(9) 0.029(8) -0.003(7) 0.002(7) -0.015(7) C15 0.042(9) 0.027(8) 0.038(9) -0.005(8) 0.000(7) -0.005(7) C16 0.038(8) 0.012(7) 0.037(9) -0.009(6) 0.004(7) -0.014(6) C21 0.038(8) 0.007(7) 0.029(8) 0.005(6) 0.011(6) 0.004(6) C22 0.036(8) 0.010(7) 0.043(9) 0.000(6) -0.002(7) 0.006(6) C23 0.041(8) 0.013(7) 0.027(8) -0.003(6) 0.006(7) 0.000(6) C24 0.046(9) 0.019(8) 0.047(10) 0.001(7) 0.014(7) 0.002(7) C25 0.032(8) 0.003(6) 0.058(10) -0.003(7) 0.005(8) -0.001(5) C26 0.028(7) 0.014(8) 0.038(8) 0.001(6) 0.008(6) 0.006(6) C31 0.049(9) 0.015(8) 0.027(8) -0.003(6) 0.006(7) -0.014(7) C32 0.039(8) 0.024(9) 0.037(9) -0.012(7) 0.002(7) -0.002(7) C33 0.054(9) 0.017(8) 0.023(8) -0.007(6) -0.003(7) -0.005(7) C34 0.061(10) 0.026(9) 0.032(9) 0.002(7) 0.005(8) -0.015(8) C35 0.062(11) 0.035(10) 0.031(9) -0.019(8) 0.011(8) -0.025(8) C36 0.040(9) 0.031(9) 0.043(10) 0.001(8) 0.008(7) -0.012(7) Cl12 0.058(3) 0.031(3) 0.079(3) 0.003(2) 0.033(2) 0.0072(19) Cl13 0.079(3) 0.054(3) 0.052(3) -0.010(2) 0.036(2) -0.018(2) Cl14 0.072(3) 0.062(3) 0.032(2) 0.009(2) 0.009(2) -0.019(2) Cl15 0.060(3) 0.035(2) 0.049(2) 0.016(2) 0.000(2) 0.0031(19) Cl16 0.054(2) 0.0188(18) 0.041(2) 0.0050(17) 0.0166(17) 0.0033(17) Cl22 0.046(2) 0.027(2) 0.056(3) -0.0073(19) 0.0112(19) -0.0067(17) Cl23 0.062(3) 0.032(2) 0.038(2) -0.0091(18) 0.0158(19) 0.0046(19) Cl24 0.064(3) 0.032(2) 0.059(3) 0.008(2) 0.034(2) -0.002(2) Cl25 0.055(2) 0.026(2) 0.070(3) -0.007(2) 0.015(2) -0.0157(19) Cl26 0.060(2) 0.028(2) 0.034(2) -0.0040(17) 0.0034(17) 0.0021(18) Cl32 0.050(2) 0.032(2) 0.037(2) 0.0031(17) 0.0095(18) 0.0108(18) Cl33 0.075(3) 0.028(2) 0.045(2) 0.0045(19) -0.003(2) 0.008(2) Cl34 0.105(4) 0.042(3) 0.034(2) 0.001(2) 0.011(2) -0.021(3) Cl35 0.076(3) 0.061(3) 0.057(3) -0.019(2) 0.035(2) -0.018(2) Cl36 0.051(3) 0.046(3) 0.071(3) -0.019(2) 0.010(2) 0.008(2) _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 S3 2.572(4) . ? Bi1 S1 2.618(4) . ? Bi1 N2 2.697(8) . ? Bi1 S2 2.698(4) . ? Bi1 N1 2.730(8) . ? S1 C11 1.742(14) . ? S3 C21 1.754(13) . ? S2 C31 1.746(14) . ? C1 C2 1.3900 . ? C1 N2 1.3900 . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 N2 1.3900 . ? C5 C6 1.422(12) . ? C6 C7 1.3900 . ? C6 N1 1.3900 . ? C7 C8 1.3900 . ? C8 C9 1.3900 . ? C9 C10 1.3900 . ? C10 N1 1.3900 . ? C11 C12 1.369(19) . ? C11 C16 1.452(19) . ? C12 C13 1.42(2) . ? C12 Cl12 1.721(15) . ? C13 C14 1.41(2) . ? C13 Cl13 1.694(16) . ? C14 C15 1.37(2) . ? C14 Cl14 1.710(15) . ? C15 C16 1.38(2) . ? C15 Cl15 1.714(15) . ? C16 Cl16 1.729(14) . ? C21 C22 1.410(19) . ? C21 C26 1.420(18) . ? C22 C23 1.382(18) . ? C22 Cl22 1.730(14) . ? C23 C24 1.405(19) . ? C23 Cl23 1.707(13) . ? C24 C25 1.41(2) . ? C24 Cl24 1.696(15) . ? C25 C26 1.375(18) . ? C25 Cl25 1.730(13) . ? C26 Cl26 1.718(14) . ? C31 C32 1.401(19) . ? C31 C36 1.427(19) . ? C32 C33 1.415(19) . ? C32 Cl32 1.708(14) . ? C33 C34 1.38(2) . ? C33 Cl33 1.725(15) . ? C34 C35 1.40(2) . ? C34 Cl34 1.710(15) . ? C35 C36 1.38(2) . ? C35 Cl35 1.728(15) . ? C36 Cl36 1.719(16) . ? 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 S3 Bi1 S1 82.17(12) . . ? S3 Bi1 N2 87.3(2) . . ? S1 Bi1 N2 88.3(2) . . ? S3 Bi1 S2 84.68(12) . . ? S1 Bi1 S2 92.56(12) . . ? N2 Bi1 S2 171.8(2) . . ? S3 Bi1 N1 90.0(2) . . ? S1 Bi1 N1 146.4(3) . . ? N2 Bi1 N1 58.6(3) . . ? S2 Bi1 N1 119.3(3) . . ? C11 S1 Bi1 96.3(4) . . ? C21 S3 Bi1 105.2(4) . . ? C31 S2 Bi1 112.6(5) . . ? C2 C1 N2 120.0 . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C3 C4 C5 120.0 . . ? N2 C5 C4 120.0 . . ? N2 C5 C6 116.1(8) . . ? C4 C5 C6 123.8(8) . . ? C5 N2 C1 120.0 . . ? C5 N2 Bi1 124.5(5) . . ? C1 N2 Bi1 115.2(5) . . ? C7 C6 N1 120.0 . . ? C7 C6 C5 123.1(9) . . ? N1 C6 C5 116.6(9) . . ? C6 C7 C8 120.0 . . ? C9 C8 C7 120.0 . . ? C8 C9 C10 120.0 . . ? N1 C10 C9 120.0 . . ? C10 N1 C6 120.0 . . ? C10 N1 Bi1 116.9(6) . . ? C6 N1 Bi1 123.0(6) . . ? C12 C11 C16 115.2(13) . . ? C12 C11 S1 122.7(11) . . ? C16 C11 S1 122.0(10) . . ? C11 C12 C13 123.9(14) . . ? C11 C12 Cl12 118.7(12) . . ? C13 C12 Cl12 117.5(12) . . ? C14 C13 C12 117.6(14) . . ? C14 C13 Cl13 121.3(12) . . ? C12 C13 Cl13 120.9(13) . . ? C15 C14 C13 120.8(14) . . ? C15 C14 Cl14 120.5(12) . . ? C13 C14 Cl14 118.7(12) . . ? C14 C15 C16 120.0(14) . . ? C14 C15 Cl15 120.2(12) . . ? C16 C15 Cl15 119.7(11) . . ? C15 C16 C11 122.5(13) . . ? C15 C16 Cl16 119.2(11) . . ? C11 C16 Cl16 118.3(11) . . ? C22 C21 C26 116.5(12) . . ? C22 C21 S3 121.2(10) . . ? C26 C21 S3 122.2(10) . . ? C23 C22 C21 122.8(12) . . ? C23 C22 Cl22 118.2(11) . . ? C21 C22 Cl22 119.1(11) . . ? C22 C23 C24 119.9(12) . . ? C22 C23 Cl23 121.1(10) . . ? C24 C23 Cl23 119.0(11) . . ? C23 C24 C25 118.3(13) . . ? C23 C24 Cl24 121.0(11) . . ? C25 C24 Cl24 120.8(11) . . ? C26 C25 C24 121.3(12) . . ? C26 C25 Cl25 119.8(11) . . ? C24 C25 Cl25 118.8(11) . . ? C25 C26 C21 121.2(13) . . ? C25 C26 Cl26 120.4(11) . . ? C21 C26 Cl26 118.4(10) . . ? C32 C31 C36 116.5(13) . . ? C32 C31 S2 124.7(11) . . ? C36 C31 S2 118.7(11) . . ? C31 C32 C33 120.9(13) . . ? C31 C32 Cl32 120.2(11) . . ? C33 C32 Cl32 118.8(11) . . ? C34 C33 C32 121.5(14) . . ? C34 C33 Cl33 119.6(11) . . ? C32 C33 Cl33 118.9(11) . . ? C33 C34 C35 118.1(14) . . ? C33 C34 Cl34 120.2(13) . . ? C35 C34 Cl34 121.6(12) . . ? C36 C35 C34 121.3(14) . . ? C36 C35 Cl35 120.3(14) . . ? C34 C35 Cl35 118.4(12) . . ? C35 C36 C31 121.6(15) . . ? C35 C36 Cl36 118.9(12) . . ? C31 C36 Cl36 119.4(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.068 _refine_diff_density_min -2.634 _refine_diff_density_rms 0.273 #===END data_10 _database_code_CSD 211641 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H7 Bi Cl15 N S3, 0.5(C6 H7 N)' _chemical_formula_sum 'C27 H10.5 Bi Cl15 N1.5 S3' _chemical_formula_weight 1192.78 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' 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 8.699(3) _cell_length_b 20.999(7) _cell_length_c 21.750(7) _cell_angle_alpha 73.156(6) _cell_angle_beta 79.295(6) _cell_angle_gamma 83.468(6) _cell_volume 3729(2) _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 Yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.125 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2276 _exptl_absorpt_coefficient_mu 5.998 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 '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 32476 _diffrn_reflns_av_R_equivalents 0.1006 _diffrn_reflns_av_sigmaI/netI 0.1520 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 13093 _reflns_number_gt 7354 _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^)+(0.0230P)^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 0.00062(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13093 _refine_ls_number_parameters 860 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1247 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 3.27739(5) 1.12065(2) -0.34279(2) 0.03017(14) Uani 1 1 d . . . Bi2 Bi 2.74666(5) 1.43714(2) -0.16536(2) 0.02487(13) Uani 1 1 d . . . C11 C 3.3421(13) 1.1633(5) -0.2063(5) 0.030(3) Uani 1 1 d . . . C12 C 3.1862(13) 1.1573(5) -0.1785(6) 0.036(3) Uani 1 1 d . . . C13 C 3.1389(13) 1.1279(5) -0.1123(6) 0.033(3) Uani 1 1 d . . . C14 C 3.2481(13) 1.1060(5) -0.0707(5) 0.029(3) Uani 1 1 d . . . C15 C 3.4049(14) 1.1149(5) -0.0968(6) 0.030(3) Uani 1 1 d . . . C16 C 3.4515(12) 1.1433(5) -0.1624(6) 0.030(3) Uani 1 1 d . . . C21 C 3.5115(13) 0.9673(5) -0.3316(5) 0.026(3) Uani 1 1 d . . . C22 C 3.6434(12) 0.9428(5) -0.3024(5) 0.025(3) Uani 1 1 d . . . C23 C 3.6504(13) 0.8824(6) -0.2557(6) 0.037(3) Uani 1 1 d . . . C24 C 3.5238(15) 0.8427(5) -0.2392(5) 0.035(3) Uani 1 1 d . . . C25 C 3.3917(13) 0.8637(5) -0.2672(5) 0.028(3) Uani 1 1 d . . . C26 C 3.3834(12) 0.9266(5) -0.3135(5) 0.029(3) Uani 1 1 d . . . C31 C 3.2835(13) 1.2372(5) -0.4947(5) 0.032(3) Uani 1 1 d . . . C32 C 3.2930(15) 1.2230(5) -0.5549(7) 0.048(4) Uani 1 1 d . . . C33 C 3.1845(15) 1.2516(5) -0.5970(6) 0.039(3) Uani 1 1 d . . . C34 C 3.0635(14) 1.2941(6) -0.5789(6) 0.039(3) Uani 1 1 d . . . C35 C 3.0546(12) 1.3109(5) -0.5210(6) 0.029(3) Uani 1 1 d . . . C36 C 3.1646(13) 1.2818(5) -0.4791(6) 0.032(3) Uani 1 1 d . . . C41 C 2.9679(12) 1.4286(5) -0.0324(5) 0.023(3) Uani 1 1 d . . . C42 C 2.8313(11) 1.4176(5) 0.0131(5) 0.021(2) Uani 1 1 d . . . C43 C 2.8342(13) 1.3916(5) 0.0800(5) 0.028(3) Uani 1 1 d . . . C44 C 2.9743(13) 1.3776(5) 0.1037(5) 0.026(3) Uani 1 1 d . . . C45 C 3.1130(13) 1.3910(4) 0.0592(6) 0.027(3) Uani 1 1 d . . . C46 C 3.1088(11) 1.4152(4) -0.0075(5) 0.018(2) Uani 1 1 d . . . C51 C 2.9593(12) 1.2928(5) -0.0988(5) 0.029(3) Uani 1 1 d . . . C52 C 2.9159(11) 1.2665(5) -0.0316(5) 0.023(3) Uani 1 1 d . . . C53 C 3.0264(13) 1.2449(5) 0.0103(5) 0.026(3) Uani 1 1 d . . . C54 C 3.1844(13) 1.2510(5) -0.0138(5) 0.026(3) Uani 1 1 d . . . C55 C 3.2357(12) 1.2781(5) -0.0795(5) 0.025(3) Uani 1 1 d . . . C56 C 3.1229(12) 1.2990(4) -0.1209(5) 0.023(3) Uani 1 1 d . . . C61 C 2.8072(12) 1.5322(5) -0.3194(5) 0.028(3) Uani 1 1 d . . . C62 C 2.6956(12) 1.5827(5) -0.3049(5) 0.028(3) Uani 1 1 d . . . C63 C 2.5869(12) 1.6122(5) -0.3448(6) 0.029(3) Uani 1 1 d . . . C64 C 2.5883(12) 1.5961(5) -0.4016(5) 0.028(3) Uani 1 1 d . . . C65 C 2.6996(14) 1.5481(5) -0.4190(5) 0.035(3) Uani 1 1 d . . . C66 C 2.8105(12) 1.5187(5) -0.3794(5) 0.024(3) Uani 1 1 d . . . C102 C 3.1316(16) 1.0807(5) -0.4758(6) 0.048(4) Uani 1 1 d . . . H102 H 3.2277 1.0567 -0.4719 0.058 Uiso 1 1 calc R . . C103 C 3.0647(18) 1.0837(6) -0.5287(7) 0.055(4) Uani 1 1 d . . . H103 H 3.1126 1.0619 -0.5596 0.066 Uiso 1 1 calc R . . C104 C 2.924(2) 1.1203(7) -0.5346(7) 0.069(5) Uani 1 1 d . . . H104 H 2.8770 1.1249 -0.5710 0.083 Uiso 1 1 calc R . . C105 C 2.8505(15) 1.1503(7) -0.4868(7) 0.056(4) Uani 1 1 d . . . H105 H 2.7542 1.1743 -0.4897 0.067 Uiso 1 1 calc R . . C106 C 2.9273(16) 1.1430(6) -0.4344(6) 0.041(3) Uani 1 1 d . . . C107 C 2.8537(14) 1.1716(6) -0.3797(6) 0.054(4) Uani 1 1 d . . . H10A H 2.8276 1.1361 -0.3410 0.081 Uiso 1 1 calc R . . H10B H 2.7603 1.1982 -0.3907 0.081 Uiso 1 1 calc R . . H10C H 2.9260 1.1989 -0.3724 0.081 Uiso 1 1 calc R . . C202 C 2.657(2) 1.3680(8) -0.2913(7) 0.086(6) Uani 1 1 d . . . H202 H 2.7475 1.3444 -0.2778 0.104 Uiso 1 1 calc R . . C203 C 2.616(2) 1.3535(8) -0.3406(8) 0.094(6) Uani 1 1 d . . . H203 H 2.6691 1.3236 -0.3627 0.113 Uiso 1 1 calc R . . C204 C 2.4698(19) 1.3941(9) -0.3539(9) 0.084(6) Uani 1 1 d . . . H204 H 2.4275 1.3859 -0.3869 0.101 Uiso 1 1 calc R . . C205 C 2.388(2) 1.4388(9) -0.3289(8) 0.076(5) Uani 1 1 d . . . H205 H 2.2998 1.4639 -0.3433 0.091 Uiso 1 1 calc R . . C206 C 2.459(2) 1.4431(8) -0.2737(8) 0.075(5) Uani 1 1 d . . . C207 C 2.3824(18) 1.4862(7) -0.2385(7) 0.076(5) Uani 1 1 d . . . H20A H 2.3290 1.4609 -0.1975 0.114 Uiso 1 1 calc R . . H20B H 2.3077 1.5154 -0.2626 0.114 Uiso 1 1 calc R . . H20C H 2.4576 1.5122 -0.2311 0.114 Uiso 1 1 calc R . . C302 C 3.4371(15) 1.0131(5) -0.2037(6) 0.036(3) Uani 1 1 d . . . H302 H 3.5186 1.0376 -0.2307 0.043 Uiso 1 1 calc R . . C303 C 3.4695(17) 0.9660(6) -0.1485(7) 0.052(4) Uani 1 1 d . . . H303 H 3.5701 0.9590 -0.1380 0.062 Uiso 1 1 calc R . . C304 C 3.350(2) 0.9295(6) -0.1091(7) 0.071(5) Uani 1 1 d . . . H304 H 3.3692 0.8965 -0.0717 0.085 Uiso 1 1 calc R . . C305 C 3.204(2) 0.9419(6) -0.1252(6) 0.060(5) Uani 1 1 d . . . H305 H 3.1221 0.9180 -0.0981 0.072 Uiso 1 1 calc R . . C306 C 3.1771(17) 0.9900(6) -0.1817(6) 0.044(3) Uani 1 1 d . . . C307 C 3.0158(16) 1.0049(7) -0.1992(6) 0.065(4) Uani 1 1 d . . . H30A H 2.9504 1.0262 -0.1692 0.097 Uiso 1 1 calc R . . H30B H 2.9724 0.9641 -0.1970 0.097 Uiso 1 1 calc R . . H30C H 3.0211 1.0340 -0.2426 0.097 Uiso 1 1 calc R . . Cl12 Cl 3.0440(3) 1.18515(14) -0.22804(15) 0.0418(8) Uani 1 1 d . . . Cl13 Cl 2.9427(3) 1.11851(14) -0.08114(15) 0.0434(8) Uani 1 1 d . . . Cl14 Cl 3.1921(4) 1.06750(15) 0.01038(15) 0.0496(9) Uani 1 1 d . . . Cl15 Cl 3.5442(4) 1.08771(15) -0.04511(16) 0.0498(9) Uani 1 1 d . . . Cl16 Cl 3.6489(3) 1.15184(15) -0.19076(15) 0.0446(8) Uani 1 1 d . . . Cl22 Cl 3.8050(3) 0.99036(14) -0.32445(16) 0.0456(8) Uani 1 1 d . . . Cl23 Cl 3.8143(4) 0.85464(15) -0.21999(16) 0.0539(9) Uani 1 1 d . . . Cl24 Cl 3.5296(4) 0.76813(14) -0.18011(16) 0.0561(10) Uani 1 1 d . . . Cl25 Cl 3.2377(4) 0.81367(15) -0.24931(16) 0.0510(9) Uani 1 1 d . . . Cl26 Cl 3.2162(4) 0.95343(14) -0.34610(15) 0.0451(8) Uani 1 1 d . . . Cl32 Cl 3.4418(4) 1.16752(15) -0.57673(17) 0.0636(11) Uani 1 1 d . . . Cl33 Cl 3.1939(5) 1.22881(17) -0.66735(16) 0.0659(11) Uani 1 1 d . . . Cl34 Cl 2.9319(4) 1.32947(16) -0.63121(16) 0.0535(9) Uani 1 1 d . . . Cl35 Cl 2.9058(4) 1.36587(16) -0.50098(16) 0.0515(9) Uani 1 1 d . . . Cl36 Cl 3.1438(4) 1.30170(15) -0.40662(15) 0.0459(8) Uani 1 1 d . . . Cl42 Cl 2.6505(3) 1.43580(13) -0.01290(13) 0.0305(7) Uani 1 1 d . . . Cl43 Cl 2.6605(3) 1.38073(14) 0.13359(14) 0.0386(7) Uani 1 1 d . . . Cl44 Cl 2.9786(4) 1.34558(14) 0.18490(14) 0.0407(8) Uani 1 1 d . . . Cl45 Cl 3.2904(3) 1.37627(13) 0.08716(14) 0.0350(7) Uani 1 1 d . . . Cl46 Cl 3.2840(3) 1.43130(13) -0.05993(13) 0.0307(7) Uani 1 1 d . . . Cl52 Cl 2.7191(3) 1.25762(14) -0.00040(15) 0.0397(8) Uani 1 1 d . . . Cl53 Cl 2.9648(4) 1.21486(13) 0.09277(14) 0.0389(8) Uani 1 1 d . . . Cl54 Cl 3.3197(3) 1.22457(14) 0.03800(15) 0.0421(8) Uani 1 1 d . . . Cl55 Cl 3.4299(3) 1.28516(13) -0.10971(14) 0.0354(7) Uani 1 1 d . . . Cl56 Cl 3.1862(3) 1.33245(13) -0.20394(13) 0.0350(7) Uani 1 1 d . . . Cl62 Cl 2.6961(4) 1.60376(14) -0.23382(14) 0.0394(8) Uani 1 1 d . . . Cl63 Cl 2.4471(4) 1.67006(15) -0.32203(16) 0.0484(9) Uani 1 1 d . . . Cl64 Cl 2.4494(4) 1.63098(16) -0.45027(15) 0.0515(9) Uani 1 1 d . . . Cl65 Cl 2.6978(4) 1.52589(17) -0.48882(15) 0.0541(9) Uani 1 1 d . . . Cl66 Cl 2.9513(4) 1.46186(15) -0.40288(15) 0.0486(9) Uani 1 1 d . . . N101 N 3.0692(12) 1.1095(4) -0.4300(5) 0.036(2) Uani 1 1 d . . . N201 N 2.5897(13) 1.4124(5) -0.2557(5) 0.042(3) Uani 1 1 d . . . N301 N 3.2925(12) 1.0259(4) -0.2213(4) 0.030(2) Uani 1 1 d . . . S1 S 3.4087(4) 1.19321(14) -0.28920(15) 0.0375(8) Uani 1 1 d . . . S2 S 3.5056(4) 1.04730(13) -0.38745(14) 0.0356(8) Uani 1 1 d . . . S32 S 3.4264(4) 1.20402(15) -0.44460(16) 0.0471(9) Uani 1 1 d . . . S40 S 2.9771(3) 1.46397(13) -0.11683(13) 0.0257(7) Uani 1 1 d . . . S50 S 2.8250(3) 1.31271(13) -0.15242(14) 0.0323(7) Uani 1 1 d . . . S60 S 2.9416(3) 1.48859(14) -0.26806(14) 0.0342(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0295(3) 0.0267(3) 0.0316(3) -0.0035(2) -0.0066(2) -0.0001(2) Bi2 0.0216(3) 0.0308(3) 0.0232(3) -0.0068(2) -0.0090(2) 0.00155(19) C11 0.033(8) 0.023(6) 0.039(8) -0.012(6) -0.011(6) -0.006(5) C12 0.026(8) 0.033(7) 0.061(10) -0.030(7) -0.002(7) -0.013(6) C13 0.020(7) 0.030(7) 0.047(9) -0.013(6) 0.005(6) -0.004(5) C14 0.033(8) 0.016(6) 0.030(7) 0.006(5) -0.001(6) -0.009(5) C15 0.040(8) 0.021(6) 0.030(8) -0.009(5) -0.015(6) 0.006(5) C16 0.027(7) 0.026(6) 0.046(8) -0.024(6) -0.002(6) -0.011(5) C21 0.027(7) 0.027(6) 0.025(7) -0.011(5) -0.001(5) 0.001(5) C22 0.016(6) 0.022(6) 0.034(7) -0.006(5) -0.005(5) 0.005(5) C23 0.028(8) 0.042(8) 0.051(9) -0.033(7) -0.011(6) 0.013(6) C24 0.047(9) 0.032(7) 0.029(8) -0.019(6) -0.001(6) 0.004(6) C25 0.025(7) 0.026(6) 0.032(7) -0.008(6) -0.003(6) -0.004(5) C26 0.024(7) 0.046(7) 0.024(7) -0.022(6) -0.004(5) 0.002(6) C31 0.031(8) 0.028(7) 0.029(8) 0.008(6) -0.004(6) -0.011(6) C32 0.064(10) 0.020(7) 0.051(10) -0.012(6) 0.010(8) 0.005(6) C33 0.056(10) 0.026(7) 0.031(8) -0.007(6) 0.000(7) -0.001(6) C34 0.038(8) 0.039(7) 0.035(8) -0.003(6) -0.007(6) -0.004(6) C35 0.018(7) 0.026(6) 0.047(8) -0.019(6) -0.002(6) -0.003(5) C36 0.028(8) 0.034(7) 0.036(8) -0.008(6) -0.009(6) -0.003(6) C41 0.034(7) 0.020(6) 0.022(7) -0.014(5) -0.011(6) 0.000(5) C42 0.012(6) 0.028(6) 0.027(7) -0.003(5) -0.008(5) -0.010(5) C43 0.042(8) 0.012(5) 0.035(8) -0.018(5) 0.001(6) -0.005(5) C44 0.035(8) 0.014(6) 0.028(7) 0.001(5) -0.006(6) -0.014(5) C45 0.035(8) 0.006(5) 0.045(8) -0.004(5) -0.018(6) -0.002(5) C46 0.022(7) 0.017(5) 0.012(6) -0.002(5) -0.001(5) -0.008(4) C51 0.026(7) 0.021(6) 0.038(8) -0.010(6) 0.005(6) -0.011(5) C52 0.012(6) 0.021(6) 0.040(8) -0.012(5) -0.004(5) -0.008(5) C53 0.032(8) 0.026(6) 0.019(7) -0.003(5) -0.005(6) -0.011(5) C54 0.028(7) 0.019(6) 0.033(8) -0.013(5) -0.006(6) 0.001(5) C55 0.017(7) 0.029(6) 0.030(8) -0.011(6) -0.004(5) 0.004(5) C56 0.027(7) 0.013(5) 0.026(7) -0.004(5) -0.003(5) -0.004(5) C61 0.027(7) 0.037(7) 0.015(7) -0.001(5) 0.000(5) -0.002(5) C62 0.020(7) 0.028(6) 0.031(7) -0.004(5) 0.002(5) -0.006(5) C63 0.014(7) 0.034(7) 0.035(8) -0.002(6) -0.007(6) 0.001(5) C64 0.026(7) 0.031(6) 0.019(7) 0.005(5) -0.006(5) 0.000(5) C65 0.036(8) 0.036(7) 0.031(8) -0.005(6) -0.004(6) -0.008(6) C66 0.027(7) 0.024(6) 0.014(6) 0.004(5) 0.001(5) -0.011(5) C102 0.076(11) 0.029(7) 0.040(9) -0.012(7) -0.014(8) 0.001(7) C103 0.067(12) 0.054(9) 0.041(10) -0.011(8) 0.005(8) -0.022(8) C104 0.088(14) 0.080(11) 0.053(11) -0.019(9) -0.023(10) -0.042(10) C105 0.032(9) 0.074(10) 0.063(11) -0.020(9) 0.003(8) -0.019(7) C106 0.057(10) 0.033(7) 0.034(8) -0.002(6) -0.008(7) -0.029(7) C107 0.037(9) 0.059(9) 0.062(10) -0.008(8) -0.005(7) -0.014(7) C202 0.137(17) 0.107(14) 0.017(9) 0.000(9) -0.001(10) -0.079(13) C203 0.145(19) 0.082(12) 0.059(13) -0.020(10) 0.005(12) -0.061(13) C204 0.040(11) 0.102(14) 0.072(14) 0.056(11) -0.026(10) -0.031(10) C205 0.069(14) 0.111(15) 0.056(12) -0.024(11) 0.004(10) -0.060(11) C206 0.056(12) 0.089(13) 0.067(13) -0.012(11) 0.029(10) -0.038(10) C207 0.088(13) 0.063(10) 0.065(12) -0.005(9) 0.025(10) -0.050(9) C302 0.060(10) 0.018(6) 0.032(8) -0.010(6) -0.010(7) 0.003(6) C303 0.061(11) 0.043(8) 0.059(11) -0.018(8) -0.025(9) 0.004(7) C304 0.155(19) 0.025(8) 0.042(10) -0.013(7) -0.039(12) 0.003(10) C305 0.116(15) 0.032(8) 0.026(9) 0.000(7) 0.014(9) -0.040(9) C306 0.077(11) 0.025(7) 0.034(8) -0.018(6) 0.001(8) -0.014(7) C307 0.060(11) 0.085(11) 0.058(10) -0.029(9) -0.001(8) -0.031(9) Cl12 0.0306(19) 0.0433(18) 0.054(2) -0.0164(16) -0.0091(16) 0.0011(14) Cl13 0.0235(18) 0.0479(18) 0.059(2) -0.0207(17) 0.0065(15) -0.0093(14) Cl14 0.050(2) 0.0470(19) 0.042(2) -0.0027(16) 0.0046(17) -0.0066(16) Cl15 0.040(2) 0.059(2) 0.047(2) -0.0059(17) -0.0128(16) -0.0028(16) Cl16 0.0219(18) 0.060(2) 0.052(2) -0.0141(17) -0.0035(15) -0.0107(15) Cl22 0.034(2) 0.0459(18) 0.060(2) -0.0165(17) -0.0099(16) -0.0075(15) Cl23 0.060(2) 0.0475(19) 0.061(2) -0.0129(18) -0.0383(19) 0.0110(17) Cl24 0.081(3) 0.0332(18) 0.046(2) 0.0049(16) -0.0173(19) -0.0023(17) Cl25 0.045(2) 0.0467(19) 0.060(2) -0.0153(17) 0.0070(17) -0.0219(16) Cl26 0.036(2) 0.0485(19) 0.055(2) -0.0121(16) -0.0217(16) 0.0009(15) Cl32 0.075(3) 0.044(2) 0.051(2) -0.0064(17) 0.0149(19) 0.0236(18) Cl33 0.093(3) 0.061(2) 0.038(2) -0.0216(19) 0.005(2) 0.009(2) Cl34 0.044(2) 0.072(2) 0.047(2) -0.0181(19) -0.0118(17) 0.0004(17) Cl35 0.041(2) 0.063(2) 0.059(2) -0.0317(19) -0.0181(18) 0.0202(17) Cl36 0.047(2) 0.0517(19) 0.046(2) -0.0235(17) -0.0156(17) 0.0063(16) Cl42 0.0203(16) 0.0453(17) 0.0276(17) -0.0115(14) -0.0066(13) 0.0002(13) Cl43 0.0325(19) 0.0546(19) 0.0281(18) -0.0080(15) -0.0016(14) -0.0146(15) Cl44 0.045(2) 0.0491(18) 0.0262(18) 0.0013(14) -0.0133(15) -0.0148(15) Cl45 0.0277(18) 0.0449(17) 0.0347(19) -0.0073(14) -0.0178(14) 0.0001(13) Cl46 0.0204(16) 0.0396(16) 0.0342(18) -0.0127(14) -0.0044(13) -0.0037(12) Cl52 0.0226(18) 0.0442(18) 0.046(2) -0.0050(15) -0.0012(14) -0.0035(14) Cl53 0.047(2) 0.0393(17) 0.0256(18) -0.0003(14) -0.0034(15) -0.0104(14) Cl54 0.037(2) 0.0486(18) 0.044(2) -0.0081(16) -0.0216(16) -0.0009(14) Cl55 0.0192(16) 0.0364(16) 0.053(2) -0.0169(15) -0.0010(14) -0.0054(13) Cl56 0.0376(19) 0.0360(16) 0.0294(18) -0.0033(14) -0.0045(14) -0.0099(13) Cl62 0.046(2) 0.0412(17) 0.038(2) -0.0191(15) -0.0119(15) -0.0005(15) Cl63 0.042(2) 0.0458(19) 0.057(2) -0.0144(17) -0.0143(17) 0.0122(15) Cl64 0.038(2) 0.070(2) 0.041(2) -0.0006(17) -0.0222(16) 0.0016(17) Cl65 0.059(2) 0.081(2) 0.026(2) -0.0190(18) -0.0102(17) -0.0041(19) Cl66 0.049(2) 0.056(2) 0.040(2) -0.0202(17) -0.0044(16) 0.0135(16) N101 0.037(7) 0.036(6) 0.032(7) -0.002(5) -0.005(5) -0.011(5) N201 0.039(8) 0.048(7) 0.030(7) 0.005(5) -0.006(6) -0.014(5) N301 0.042(7) 0.019(5) 0.032(6) -0.013(5) 0.001(5) -0.007(5) S1 0.037(2) 0.0340(17) 0.042(2) -0.0086(15) -0.0067(16) -0.0091(14) S2 0.037(2) 0.0278(16) 0.0333(19) 0.0008(14) -0.0006(15) 0.0037(13) S32 0.036(2) 0.0401(19) 0.046(2) 0.0125(16) -0.0013(17) 0.0055(15) S40 0.0253(17) 0.0275(15) 0.0262(17) -0.0069(13) -0.0073(13) -0.0052(12) S50 0.0318(19) 0.0305(16) 0.0381(19) -0.0061(14) -0.0180(15) -0.0046(13) S60 0.0261(18) 0.0438(18) 0.0275(19) -0.0021(15) -0.0056(14) 0.0011(14) _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 S2 2.590(3) . ? Bi1 S32 2.617(3) . ? Bi1 S1 2.627(3) . ? Bi2 S50 2.571(3) . ? Bi2 S60 2.578(3) . ? Bi2 S40 2.615(3) . ? Bi2 N201 2.783(10) . ? C11 C12 1.382(14) . ? C11 C16 1.417(14) . ? C11 S1 1.737(12) . ? C12 C13 1.395(15) . ? C12 Cl12 1.731(12) . ? C13 C14 1.384(14) . ? C13 Cl13 1.727(11) . ? C14 C15 1.388(15) . ? C14 Cl14 1.715(11) . ? C15 C16 1.381(14) . ? C15 Cl15 1.741(11) . ? C16 Cl16 1.724(11) . ? C21 C22 1.390(13) . ? C21 C26 1.409(14) . ? C21 S2 1.767(11) . ? C22 C23 1.380(14) . ? C22 Cl22 1.731(10) . ? C23 C24 1.388(15) . ? C23 Cl23 1.713(11) . ? C24 C25 1.369(14) . ? C24 Cl24 1.716(12) . ? C25 C26 1.414(14) . ? C25 Cl25 1.714(10) . ? C26 Cl26 1.703(11) . ? C31 C36 1.377(14) . ? C31 C32 1.413(15) . ? C31 S32 1.756(11) . ? C32 C33 1.400(16) . ? C32 Cl32 1.733(12) . ? C33 C34 1.377(15) . ? C33 Cl33 1.717(12) . ? C34 C35 1.388(14) . ? C34 Cl34 1.720(12) . ? C35 C36 1.410(14) . ? C35 Cl35 1.715(10) . ? C36 Cl36 1.718(11) . ? C41 C42 1.393(14) . ? C41 C46 1.398(13) . ? C41 S40 1.761(10) . ? C42 C43 1.401(14) . ? C42 Cl42 1.735(10) . ? C43 C44 1.379(14) . ? C43 Cl43 1.721(11) . ? C44 C45 1.399(14) . ? C44 Cl44 1.704(11) . ? C45 C46 1.396(13) . ? C45 Cl45 1.726(10) . ? C46 Cl46 1.728(10) . ? C51 C52 1.400(14) . ? C51 C56 1.423(14) . ? C51 S50 1.735(11) . ? C52 C53 1.396(13) . ? C52 Cl52 1.730(10) . ? C53 C54 1.383(14) . ? C53 Cl53 1.721(10) . ? C54 C55 1.384(14) . ? C54 Cl54 1.716(10) . ? C55 C56 1.403(13) . ? C55 Cl55 1.702(10) . ? C56 Cl56 1.744(10) . ? C61 C66 1.406(13) . ? C61 C62 1.419(14) . ? C61 S60 1.762(11) . ? C62 C63 1.376(14) . ? C62 Cl62 1.727(11) . ? C63 C64 1.370(14) . ? C63 Cl63 1.729(11) . ? C64 C65 1.399(14) . ? C64 Cl64 1.715(10) . ? C65 C66 1.386(14) . ? C65 Cl65 1.715(11) . ? C66 Cl66 1.725(10) . ? C102 N101 1.314(13) . ? C102 C103 1.366(16) . ? C103 C104 1.379(18) . ? C104 C105 1.388(17) . ? C105 C106 1.389(16) . ? C106 N101 1.354(14) . ? C106 C107 1.492(16) . ? C202 C203 1.311(18) . ? C202 N201 1.392(18) . ? C203 C204 1.48(2) . ? C204 C205 1.30(2) . ? C205 C206 1.48(2) . ? C206 N201 1.309(18) . ? C206 C207 1.387(18) . ? C302 N301 1.357(13) . ? C302 C303 1.370(15) . ? C303 C304 1.365(19) . ? C304 C305 1.357(19) . ? C305 C306 1.386(17) . ? C306 N301 1.340(14) . ? C306 C307 1.496(17) . ? 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 S2 Bi1 S32 76.00(9) . . ? S2 Bi1 S1 105.28(10) . . ? S32 Bi1 S1 77.89(11) . . ? S50 Bi2 S60 99.83(10) . . ? S50 Bi2 S40 97.48(8) . . ? S60 Bi2 S40 77.38(9) . . ? S50 Bi2 N201 79.0(2) . . ? S60 Bi2 N201 82.7(2) . . ? S40 Bi2 N201 158.9(2) . . ? C12 C11 C16 115.8(11) . . ? C12 C11 S1 124.6(9) . . ? C16 C11 S1 119.6(9) . . ? C11 C12 C13 122.6(11) . . ? C11 C12 Cl12 118.9(10) . . ? C13 C12 Cl12 118.6(9) . . ? C14 C13 C12 120.6(10) . . ? C14 C13 Cl13 119.0(9) . . ? C12 C13 Cl13 120.4(9) . . ? C13 C14 C15 117.9(10) . . ? C13 C14 Cl14 121.1(9) . . ? C15 C14 Cl14 121.0(9) . . ? C16 C15 C14 121.3(10) . . ? C16 C15 Cl15 120.1(9) . . ? C14 C15 Cl15 118.6(9) . . ? C15 C16 C11 121.6(10) . . ? C15 C16 Cl16 118.2(9) . . ? C11 C16 Cl16 120.2(9) . . ? C22 C21 C26 117.3(10) . . ? C22 C21 S2 120.5(8) . . ? C26 C21 S2 122.1(8) . . ? C23 C22 C21 122.8(10) . . ? C23 C22 Cl22 118.4(8) . . ? C21 C22 Cl22 118.9(8) . . ? C22 C23 C24 119.0(11) . . ? C22 C23 Cl23 121.2(9) . . ? C24 C23 Cl23 119.8(10) . . ? C25 C24 C23 120.8(11) . . ? C25 C24 Cl24 119.7(9) . . ? C23 C24 Cl24 119.4(10) . . ? C24 C25 C26 119.9(10) . . ? C24 C25 Cl25 121.1(9) . . ? C26 C25 Cl25 119.0(9) . . ? C21 C26 C25 120.2(10) . . ? C21 C26 Cl26 120.3(9) . . ? C25 C26 Cl26 119.5(8) . . ? C36 C31 C32 117.3(11) . . ? C36 C31 S32 121.4(9) . . ? C32 C31 S32 121.1(9) . . ? C33 C32 C31 121.9(11) . . ? C33 C32 Cl32 119.2(10) . . ? C31 C32 Cl32 118.9(10) . . ? C34 C33 C32 119.3(11) . . ? C34 C33 Cl33 120.3(10) . . ? C32 C33 Cl33 120.1(9) . . ? C33 C34 C35 119.9(11) . . ? C33 C34 Cl34 118.9(10) . . ? C35 C34 Cl34 121.1(9) . . ? C34 C35 C36 120.2(10) . . ? C34 C35 Cl35 118.9(9) . . ? C36 C35 Cl35 120.9(9) . . ? C31 C36 C35 121.2(10) . . ? C31 C36 Cl36 120.4(9) . . ? C35 C36 Cl36 118.3(9) . . ? C42 C41 C46 116.2(9) . . ? C42 C41 S40 125.7(8) . . ? C46 C41 S40 117.8(8) . . ? C41 C42 C43 122.2(9) . . ? C41 C42 Cl42 119.6(8) . . ? C43 C42 Cl42 118.2(8) . . ? C44 C43 C42 120.8(10) . . ? C44 C43 Cl43 119.5(9) . . ? C42 C43 Cl43 119.6(9) . . ? C43 C44 C45 118.1(10) . . ? C43 C44 Cl44 121.0(9) . . ? C45 C44 Cl44 120.9(9) . . ? C46 C45 C44 120.5(10) . . ? C46 C45 Cl45 120.0(9) . . ? C44 C45 Cl45 119.4(9) . . ? C45 C46 C41 122.1(9) . . ? C45 C46 Cl46 118.3(8) . . ? C41 C46 Cl46 119.6(8) . . ? C52 C51 C56 115.4(10) . . ? C52 C51 S50 122.7(8) . . ? C56 C51 S50 121.9(9) . . ? C53 C52 C51 122.2(10) . . ? C53 C52 Cl52 119.2(9) . . ? C51 C52 Cl52 118.6(8) . . ? C54 C53 C52 120.1(10) . . ? C54 C53 Cl53 120.0(8) . . ? C52 C53 Cl53 119.8(9) . . ? C53 C54 C55 120.9(10) . . ? C53 C54 Cl54 120.0(9) . . ? C55 C54 Cl54 119.1(8) . . ? C54 C55 C56 118.1(10) . . ? C54 C55 Cl55 121.3(8) . . ? C56 C55 Cl55 120.6(8) . . ? C55 C56 C51 123.3(10) . . ? C55 C56 Cl56 118.5(8) . . ? C51 C56 Cl56 118.2(8) . . ? C66 C61 C62 116.7(10) . . ? C66 C61 S60 119.7(8) . . ? C62 C61 S60 123.6(8) . . ? C63 C62 C61 121.1(10) . . ? C63 C62 Cl62 121.1(8) . . ? C61 C62 Cl62 117.8(8) . . ? C64 C63 C62 120.9(10) . . ? C64 C63 Cl63 120.2(8) . . ? C62 C63 Cl63 118.8(9) . . ? C63 C64 C65 119.9(10) . . ? C63 C64 Cl64 121.0(8) . . ? C65 C64 Cl64 119.0(9) . . ? C66 C65 C64 119.4(10) . . ? C66 C65 Cl65 120.5(9) . . ? C64 C65 Cl65 120.1(9) . . ? C65 C66 C61 121.6(10) . . ? C65 C66 Cl66 119.0(8) . . ? C61 C66 Cl66 119.4(8) . . ? N101 C102 C103 124.3(13) . . ? C102 C103 C104 117.5(13) . . ? C103 C104 C105 120.5(13) . . ? C104 C105 C106 117.2(14) . . ? N101 C106 C105 122.2(12) . . ? N101 C106 C107 117.3(11) . . ? C105 C106 C107 120.5(13) . . ? C203 C202 N201 131.7(19) . . ? C202 C203 C204 106.4(17) . . ? C205 C204 C203 133(2) . . ? C204 C205 C206 108(2) . . ? N201 C206 C207 116.3(17) . . ? N201 C206 C205 127.0(16) . . ? C207 C206 C205 116.7(18) . . ? N301 C302 C303 123.6(12) . . ? C304 C303 C302 118.4(14) . . ? C305 C304 C303 119.2(14) . . ? C304 C305 C306 120.5(14) . . ? N301 C306 C305 121.3(13) . . ? N301 C306 C307 117.9(12) . . ? C305 C306 C307 120.8(13) . . ? C102 N101 C106 118.2(11) . . ? C206 N201 C202 113.2(13) . . ? C206 N201 Bi2 126.3(10) . . ? C202 N201 Bi2 120.2(9) . . ? C306 N301 C302 117.1(11) . . ? C11 S1 Bi1 104.5(3) . . ? C21 S2 Bi1 109.0(4) . . ? C31 S32 Bi1 104.2(4) . . ? C41 S40 Bi2 114.7(3) . . ? C51 S50 Bi2 104.7(3) . . ? C61 S60 Bi2 99.2(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.292 _refine_diff_density_min -0.938 _refine_diff_density_rms 0.188 #===END data_11 _database_code_CSD 211642 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H7 Bi F15 N S3' _chemical_formula_sum 'C24 H7 Bi F15 N S3' _chemical_formula_weight 899.47 _chemical_absolute_configuration unk 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' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.4276(5) _cell_length_b 19.4615(17) _cell_length_c 25.877(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2733.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 101 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 6.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.396 _exptl_absorpt_correction_T_max 0.710 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD area detector' _diffrn_measurement_method '/w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14692 _diffrn_reflns_av_R_equivalents 0.0802 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4834 _reflns_number_gt 3590 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0257P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.218(9) _refine_ls_number_reflns 4834 _refine_ls_number_parameters 399 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.977 _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 0.82617(7) 0.12361(2) 0.214222(13) 0.02855(10) Uani 1 1 d . . . N1 N 0.6975(15) 0.1241(5) 0.3149(2) 0.0359(17) Uani 1 1 d . . . C1 C 0.629(3) 0.1819(7) 0.3369(5) 0.056(4) Uani 1 1 d . . . H1A H 0.6542 0.2234 0.3183 0.067 Uiso 1 1 calc R . . C2 C 0.525(3) 0.1861(8) 0.3850(6) 0.078(6) Uani 1 1 d . . . H2A H 0.4734 0.2289 0.3989 0.094 Uiso 1 1 calc R . . C3 C 0.499(3) 0.1256(10) 0.4125(4) 0.079(4) Uani 1 1 d . . . C4 C 0.563(3) 0.0649(7) 0.3883(5) 0.067(5) Uani 1 1 d . . . H4A H 0.5352 0.0222 0.4052 0.080 Uiso 1 1 calc R . . C5 C 0.663(3) 0.0664(6) 0.3414(5) 0.059(4) Uani 1 1 d . . . H5A H 0.7120 0.0242 0.3262 0.071 Uiso 1 1 calc R . . C6 C 0.402(3) 0.1291(12) 0.4675(6) 0.124(6) Uani 1 1 d U . . H6A H 0.4116 0.1766 0.4801 0.186 Uiso 1 1 calc R . . H6B H 0.5017 0.0994 0.4898 0.186 Uiso 1 1 calc R . . H6C H 0.2301 0.1137 0.4683 0.186 Uiso 1 1 calc R . . S1 S 1.1372(7) 0.03545(15) 0.24828(11) 0.0426(8) Uani 1 1 d . . . C11 C 1.0956(17) -0.0289(5) 0.2019(4) 0.027(3) Uani 1 1 d . . . F12 F 0.7264(12) -0.0669(3) 0.2410(2) 0.0429(19) Uani 1 1 d . . . C12 C 0.897(2) -0.0749(6) 0.2037(4) 0.033(3) Uani 1 1 d . . . F13 F 0.6703(16) -0.1676(3) 0.1713(2) 0.0479(17) Uani 1 1 d . . . C13 C 0.8664(18) -0.1246(10) 0.1688(4) 0.037(3) Uani 1 1 d . . . C14 C 1.038(2) -0.1343(8) 0.1300(4) 0.039(3) Uani 1 1 d . . . F14 F 1.0072(14) -0.1861(4) 0.0953(3) 0.056(2) Uani 1 1 d . . . F15 F 1.4020(12) -0.1011(3) 0.0893(2) 0.052(2) Uani 1 1 d . . . C15 C 1.237(2) -0.0917(6) 0.1274(4) 0.038(3) Uani 1 1 d . . . F16 F 1.4634(12) 0.0002(4) 0.1574(3) 0.0483(19) Uani 1 1 d . . . C16 C 1.2622(19) -0.0399(6) 0.1625(4) 0.030(3) Uani 1 1 d . . . S2 S 1.0668(4) 0.12270(19) 0.12622(8) 0.0329(6) Uani 1 1 d . . . C21 C 0.8152(19) 0.1224(7) 0.0834(3) 0.0289(19) Uani 1 1 d . . . F22 F 0.8386(14) 0.0025(3) 0.0707(2) 0.0467(16) Uani 1 1 d . . . C22 C 0.731(2) 0.0627(6) 0.0600(4) 0.035(3) Uani 1 1 d . . . C23 C 0.533(3) 0.0609(6) 0.0262(5) 0.041(3) Uani 1 1 d . . . F23 F 0.4554(14) 0.0029(3) 0.0051(2) 0.057(2) Uani 1 1 d . . . F24 F 0.2183(10) 0.1230(4) -0.0163(2) 0.0483(15) Uani 1 1 d . . . C24 C 0.4177(16) 0.1221(8) 0.0146(3) 0.032(2) Uani 1 1 d . . . C25 C 0.500(2) 0.1828(6) 0.0357(4) 0.031(3) Uani 1 1 d . . . F25 F 0.3816(12) 0.2419(3) 0.0252(2) 0.0449(18) Uani 1 1 d . . . F26 F 0.7749(12) 0.2431(3) 0.0877(2) 0.0391(18) Uani 1 1 d . . . C26 C 0.696(2) 0.1824(5) 0.0689(4) 0.030(3) Uani 1 1 d . . . S3 S 1.1097(6) 0.21779(16) 0.24904(11) 0.0433(9) Uani 1 1 d . . . C31 C 1.055(2) 0.2835(5) 0.2038(4) 0.035(3) Uani 1 1 d . . . F32 F 1.4185(11) 0.2576(4) 0.1585(3) 0.049(2) Uani 1 1 d . . . C32 C 1.217(2) 0.2969(6) 0.1634(5) 0.037(3) Uani 1 1 d . . . F33 F 1.3461(15) 0.3630(4) 0.0923(2) 0.060(2) Uani 1 1 d . . . C33 C 1.178(3) 0.3505(5) 0.1297(4) 0.040(3) Uani 1 1 d . . . C34 C 0.986(2) 0.3917(6) 0.1351(4) 0.038(4) Uani 1 1 d . . . F34 F 0.9476(14) 0.4453(4) 0.1026(3) 0.057(2) Uani 1 1 d . . . F35 F 0.6144(14) 0.4208(4) 0.1786(3) 0.050(2) Uani 1 1 d . . . C35 C 0.812(2) 0.3815(8) 0.1742(3) 0.028(2) Uani 1 1 d . . . F36 F 0.6825(14) 0.3165(3) 0.2451(2) 0.0423(16) Uani 1 1 d . . . C36 C 0.853(2) 0.3259(5) 0.2081(5) 0.037(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 Bi1 0.03521(18) 0.02671(16) 0.02374(15) 0.0010(2) -0.0028(2) -0.0016(2) N1 0.042(5) 0.041(4) 0.024(4) 0.002(5) 0.000(4) 0.003(7) C1 0.079(11) 0.054(9) 0.035(7) 0.004(6) 0.019(8) 0.016(8) C2 0.136(15) 0.034(9) 0.065(11) -0.001(8) 0.050(11) 0.001(9) C3 0.147(12) 0.050(8) 0.038(7) -0.007(9) 0.045(8) -0.017(13) C4 0.129(15) 0.034(8) 0.039(8) 0.004(7) 0.028(9) -0.026(8) C5 0.104(11) 0.029(7) 0.044(8) -0.001(6) 0.015(10) 0.000(9) C6 0.124(6) 0.124(6) 0.123(6) 0.0000(10) 0.0008(10) -0.0001(10) S1 0.057(3) 0.0383(17) 0.0328(16) 0.0002(13) -0.0113(17) 0.0077(18) C11 0.027(7) 0.032(6) 0.021(7) 0.005(5) -0.008(5) 0.006(4) F12 0.040(5) 0.051(4) 0.038(4) 0.011(3) 0.012(3) 0.010(3) C12 0.035(7) 0.040(7) 0.022(7) 0.006(5) -0.007(5) 0.005(5) F13 0.049(4) 0.043(4) 0.052(4) 0.011(3) -0.013(5) -0.005(4) C13 0.036(7) 0.035(6) 0.041(6) 0.026(8) -0.008(5) -0.010(8) C14 0.042(7) 0.032(9) 0.042(7) -0.004(7) -0.009(6) 0.006(7) F14 0.085(6) 0.036(4) 0.046(4) -0.010(4) -0.004(4) 0.010(4) F15 0.061(5) 0.059(6) 0.034(4) 0.007(3) 0.015(3) 0.019(3) C15 0.044(9) 0.051(8) 0.017(6) 0.008(5) 0.002(5) 0.020(6) F16 0.043(4) 0.050(5) 0.052(4) 0.013(4) 0.008(4) 0.002(4) C16 0.028(8) 0.030(6) 0.031(6) 0.004(5) -0.002(5) 0.006(5) S2 0.0334(13) 0.0413(14) 0.0240(12) 0.0039(16) -0.0014(10) -0.0014(17) C21 0.037(5) 0.032(5) 0.018(4) 0.003(6) 0.012(5) 0.007(9) F22 0.062(4) 0.035(3) 0.043(3) 0.006(3) -0.011(4) 0.011(4) C22 0.044(9) 0.030(7) 0.029(6) 0.006(5) -0.003(5) 0.006(5) C23 0.060(9) 0.028(7) 0.034(7) -0.003(6) 0.001(7) -0.010(6) F23 0.085(6) 0.036(4) 0.048(4) 0.000(4) -0.014(4) -0.011(4) F24 0.050(4) 0.054(4) 0.041(3) -0.006(4) -0.020(3) -0.002(5) C24 0.035(6) 0.040(6) 0.022(5) 0.007(7) -0.002(4) -0.012(7) C25 0.036(7) 0.033(7) 0.025(6) 0.005(5) -0.001(5) 0.008(6) F25 0.050(5) 0.041(4) 0.044(4) 0.000(3) -0.012(3) 0.009(3) F26 0.051(5) 0.029(3) 0.038(3) -0.004(3) -0.002(3) 0.002(3) C26 0.041(7) 0.032(6) 0.016(5) -0.003(4) 0.002(6) 0.002(6) S3 0.057(3) 0.0378(18) 0.0354(18) 0.0008(14) -0.0101(15) -0.0134(16) C31 0.040(7) 0.029(6) 0.035(8) 0.001(6) 0.000(6) -0.010(5) F32 0.035(4) 0.052(5) 0.061(5) -0.015(4) 0.009(3) -0.008(3) C32 0.023(7) 0.044(7) 0.043(7) -0.020(6) 0.010(6) -0.005(6) F33 0.076(4) 0.064(5) 0.040(3) -0.002(4) 0.027(4) -0.021(5) C33 0.064(8) 0.026(6) 0.028(6) 0.001(5) 0.013(8) -0.004(7) C34 0.060(8) 0.028(9) 0.026(6) -0.006(5) -0.006(6) -0.006(6) F34 0.089(6) 0.039(4) 0.042(4) 0.008(4) -0.002(4) -0.014(4) F35 0.055(6) 0.035(4) 0.059(5) -0.008(4) -0.004(4) -0.004(4) C35 0.027(5) 0.025(6) 0.031(5) -0.003(6) -0.003(5) -0.005(8) F36 0.043(4) 0.047(4) 0.037(3) 0.000(3) 0.016(4) -0.007(4) C36 0.040(7) 0.042(6) 0.029(7) -0.009(6) 0.024(7) -0.025(6) _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 S3 2.557(3) . ? Bi1 S1 2.563(3) . ? Bi1 S2 2.625(2) . ? Bi1 N1 2.696(7) . ? N1 C1 1.313(14) . ? N1 C5 1.331(14) . ? C1 C2 1.369(17) . ? C2 C3 1.38(2) . ? C3 C4 1.38(2) . ? C3 C6 1.519(17) . ? C4 C5 1.331(16) . ? S1 C11 1.750(11) . ? C11 C16 1.379(13) . ? C11 C12 1.403(15) . ? F12 C12 1.344(12) . ? C12 C13 1.333(18) . ? F13 C13 1.356(15) . ? C13 C14 1.382(15) . ? C14 F14 1.360(15) . ? C14 C15 1.363(16) . ? F15 C15 1.344(12) . ? C15 C16 1.364(15) . ? F16 C16 1.349(11) . ? S2 C21 1.758(10) . ? C21 C26 1.386(15) . ? C21 C22 1.387(15) . ? F22 C22 1.339(12) . ? C22 C23 1.385(15) . ? C23 F23 1.324(13) . ? C23 C24 1.379(18) . ? F24 C24 1.345(9) . ? C24 C25 1.378(17) . ? C25 F25 1.345(12) . ? C25 C26 1.368(15) . ? F26 C26 1.345(11) . ? S3 C31 1.759(11) . ? C31 C36 1.376(15) . ? C31 C32 1.392(15) . ? F32 C32 1.341(12) . ? C32 C33 1.375(15) . ? F33 C33 1.353(13) . ? C33 C34 1.322(16) . ? C34 F34 1.356(13) . ? C34 C35 1.396(15) . ? F35 C35 1.324(14) . ? C35 C36 1.409(17) . ? F36 C36 1.346(12) . ? 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 S3 Bi1 S1 87.84(8) . . ? S3 Bi1 S2 90.63(10) . . ? S1 Bi1 S2 88.06(10) . . ? S3 Bi1 N1 79.2(2) . . ? S1 Bi1 N1 80.9(2) . . ? S2 Bi1 N1 165.18(18) . . ? C1 N1 C5 117.3(8) . . ? C1 N1 Bi1 119.7(7) . . ? C5 N1 Bi1 122.2(8) . . ? N1 C1 C2 124.3(13) . . ? C1 C2 C3 117.3(13) . . ? C4 C3 C2 117.9(10) . . ? C4 C3 C6 123.4(17) . . ? C2 C3 C6 118.7(16) . . ? C5 C4 C3 119.8(12) . . ? C4 C5 N1 123.2(12) . . ? C11 S1 Bi1 99.1(3) . . ? C16 C11 C12 115.5(10) . . ? C16 C11 S1 122.3(8) . . ? C12 C11 S1 122.2(8) . . ? C13 C12 F12 119.0(10) . . ? C13 C12 C11 122.3(11) . . ? F12 C12 C11 118.6(10) . . ? C12 C13 F13 120.8(10) . . ? C12 C13 C14 120.6(13) . . ? F13 C13 C14 118.6(15) . . ? F14 C14 C15 121.0(11) . . ? F14 C14 C13 119.9(13) . . ? C15 C14 C13 119.1(13) . . ? F15 C15 C14 118.8(11) . . ? F15 C15 C16 121.4(11) . . ? C14 C15 C16 119.7(11) . . ? F16 C16 C15 116.4(10) . . ? F16 C16 C11 120.8(10) . . ? C15 C16 C11 122.7(11) . . ? C21 S2 Bi1 99.2(3) . . ? C26 C21 C22 115.7(9) . . ? C26 C21 S2 121.9(9) . . ? C22 C21 S2 122.3(9) . . ? F22 C22 C23 116.5(11) . . ? F22 C22 C21 120.0(10) . . ? C23 C22 C21 123.5(10) . . ? F23 C23 C24 120.0(12) . . ? F23 C23 C22 122.0(12) . . ? C24 C23 C22 117.9(11) . . ? F24 C24 C25 119.1(12) . . ? F24 C24 C23 120.5(12) . . ? C25 C24 C23 120.4(9) . . ? F25 C25 C26 120.3(10) . . ? F25 C25 C24 119.8(10) . . ? C26 C25 C24 119.9(11) . . ? F26 C26 C25 117.9(10) . . ? F26 C26 C21 119.6(10) . . ? C25 C26 C21 122.5(10) . . ? C31 S3 Bi1 100.6(4) . . ? C36 C31 C32 116.8(11) . . ? C36 C31 S3 121.2(9) . . ? C32 C31 S3 122.0(10) . . ? F32 C32 C33 120.0(11) . . ? F32 C32 C31 118.6(11) . . ? C33 C32 C31 121.4(12) . . ? C34 C33 F33 119.9(11) . . ? C34 C33 C32 120.9(12) . . ? F33 C33 C32 119.0(13) . . ? C33 C34 F34 121.4(11) . . ? C33 C34 C35 121.5(12) . . ? F34 C34 C35 117.1(12) . . ? F35 C35 C34 121.8(12) . . ? F35 C35 C36 121.2(10) . . ? C34 C35 C36 116.9(12) . . ? F36 C36 C31 121.5(11) . . ? F36 C36 C35 116.0(11) . . ? C31 C36 C35 122.4(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.036 _refine_diff_density_min -0.748 _refine_diff_density_rms 0.139 #===END data_12 _database_code_CSD 211643 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, C12 H15 N2, C66 Bi3 F55 S11' _chemical_formula_sum 'C84 H23 Bi3 F55 N3 S11' _chemical_formula_weight 3097.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.128(8) _cell_length_b 28.483(15) _cell_length_c 22.941(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.93(4) _cell_angle_gamma 90.00 _cell_volume 9737(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 149 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5869 _exptl_absorpt_coefficient_mu 5.798 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.244 _exptl_absorpt_correction_T_max 0.310 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD area detector' _diffrn_measurement_method '/w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 51982 _diffrn_reflns_av_R_equivalents 0.1158 _diffrn_reflns_av_sigmaI/netI 0.1359 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 17128 _reflns_number_gt 9651 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0347P)^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 17128 _refine_ls_number_parameters 1396 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1311 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.43719(3) 1.132626(14) 0.62993(2) 0.03288(12) Uani 1 1 d . . . Bi2 Bi 0.25700(3) 1.144226(15) 0.75282(2) 0.03426(13) Uani 1 1 d . . . Bi3 Bi 0.04648(3) 1.114019(14) 0.86739(2) 0.03560(13) Uani 1 1 d . . . S1 S 0.5580(2) 1.13435(10) 0.72396(14) 0.0394(8) Uani 1 1 d . . . C1 C 0.6241(8) 1.0843(4) 0.7186(5) 0.040(3) Uani 1 1 d . . . C2 C 0.6137(9) 1.0424(4) 0.7489(5) 0.042(3) Uani 1 1 d . . . F2 F 0.5524(5) 1.0413(2) 0.7846(3) 0.057(2) Uani 1 1 d . . . C3 C 0.6669(11) 1.0037(5) 0.7450(7) 0.066(5) Uani 1 1 d . . . F3 F 0.6568(6) 0.9662(3) 0.7774(4) 0.086(3) Uani 1 1 d . . . C4 C 0.7323(9) 1.0061(5) 0.7095(7) 0.054(4) Uani 1 1 d . . . F4 F 0.7853(6) 0.9688(3) 0.7086(4) 0.089(3) Uani 1 1 d . . . C5 C 0.7417(9) 1.0456(5) 0.6770(6) 0.055(4) Uani 1 1 d . . . F5 F 0.8036(5) 1.0463(3) 0.6415(4) 0.083(3) Uani 1 1 d . . . C6 C 0.6893(9) 1.0837(4) 0.6821(6) 0.046(3) Uani 1 1 d . . . F6 F 0.7005(5) 1.1210(3) 0.6487(3) 0.063(2) Uani 1 1 d . . . S2 S 0.5291(3) 1.18484(14) 0.5664(2) 0.0777(13) Uani 1 1 d . . . C21 C 0.4342(9) 1.2195(5) 0.5405(6) 0.048(4) Uani 1 1 d . . . F21 F 0.3636(6) 1.1627(3) 0.4756(4) 0.081(3) Uani 1 1 d . . . C22 C 0.3624(10) 1.2059(5) 0.4990(6) 0.054(4) Uani 1 1 d . . . C23 C 0.2915(11) 1.2345(5) 0.4785(6) 0.057(4) Uani 1 1 d . . . F23 F 0.2234(6) 1.2187(3) 0.4384(4) 0.096(3) Uani 1 1 d . . . C24 C 0.2881(11) 1.2782(5) 0.4999(7) 0.055(4) Uani 1 1 d . . . F24 F 0.2171(6) 1.3073(3) 0.4817(4) 0.087(3) Uani 1 1 d . . . C25 C 0.3566(13) 1.2941(4) 0.5436(7) 0.063(5) Uani 1 1 d . . . F25 F 0.3538(7) 1.3374(3) 0.5641(4) 0.094(3) Uani 1 1 d . . . C26 C 0.4274(10) 1.2657(5) 0.5615(6) 0.056(4) Uani 1 1 d . . . F26 F 0.4946(6) 1.2829(3) 0.6038(4) 0.094(3) Uani 1 1 d . . . S3 S 0.4840(3) 1.05140(10) 0.59647(15) 0.0529(10) Uani 1 1 d . . . C31 C 0.4899(8) 1.0598(4) 0.5211(5) 0.037(3) Uani 1 1 d . . . C32 C 0.5720(10) 1.0622(4) 0.5008(8) 0.062(4) Uani 1 1 d . . . F32 F 0.6480(6) 1.0583(3) 0.5401(4) 0.090(3) Uani 1 1 d . . . C33 C 0.5758(15) 1.0641(5) 0.4426(10) 0.087(7) Uani 1 1 d . . . F33 F 0.6591(8) 1.0646(3) 0.4267(5) 0.123(4) Uani 1 1 d . . . C34 C 0.4974(19) 1.0666(5) 0.4013(7) 0.089(8) Uani 1 1 d . . . F34 F 0.5072(9) 1.0696(3) 0.3445(4) 0.134(5) Uani 1 1 d . . . C35 C 0.4170(13) 1.0664(5) 0.4208(7) 0.066(5) Uani 1 1 d . . . F35 F 0.3440(8) 1.0694(3) 0.3786(4) 0.118(4) Uani 1 1 d . . . C36 C 0.4138(9) 1.0625(4) 0.4784(6) 0.037(3) Uani 1 1 d . . . F36 F 0.3330(6) 1.0614(3) 0.4948(4) 0.073(2) Uani 1 1 d . . . S4 S 0.3531(2) 1.06863(9) 0.70692(13) 0.0324(7) Uani 1 1 d . . . C41 C 0.2725(7) 1.0366(4) 0.6589(5) 0.026(3) Uani 1 1 d . . . C42 C 0.2270(8) 1.0529(3) 0.6047(5) 0.032(3) Uani 1 1 d . . . F42 F 0.2383(4) 1.0983(2) 0.5894(3) 0.0428(17) Uani 1 1 d . . . C43 C 0.1685(8) 1.0266(4) 0.5653(5) 0.036(3) Uani 1 1 d . . . F43 F 0.1282(5) 1.0440(2) 0.5139(3) 0.054(2) Uani 1 1 d . . . C44 C 0.1532(8) 0.9808(4) 0.5804(6) 0.039(3) Uani 1 1 d . . . F44 F 0.0957(5) 0.9541(2) 0.5436(3) 0.065(2) Uani 1 1 d . . . C45 C 0.1962(8) 0.9624(4) 0.6338(5) 0.033(3) Uani 1 1 d . . . F45 F 0.1802(5) 0.9180(2) 0.6482(3) 0.060(2) Uani 1 1 d . . . C46 C 0.2537(8) 0.9901(4) 0.6718(5) 0.035(3) Uani 1 1 d . . . F46 F 0.2934(5) 0.9708(2) 0.7230(3) 0.0469(18) Uani 1 1 d . . . S5 S 0.3824(2) 1.20646(10) 0.72731(14) 0.0394(8) Uani 1 1 d . . . C51 C 0.3098(8) 1.2509(4) 0.6921(5) 0.035(3) Uani 1 1 d . . . C52 C 0.3248(10) 1.2975(5) 0.7071(6) 0.053(4) Uani 1 1 d . . . F52 F 0.3949(6) 1.3094(2) 0.7484(4) 0.072(2) Uani 1 1 d . . . C53 C 0.2699(12) 1.3322(5) 0.6797(8) 0.070(5) Uani 1 1 d . . . F53 F 0.2876(7) 1.3775(3) 0.6963(5) 0.103(3) Uani 1 1 d . . . C54 C 0.1992(11) 1.3222(6) 0.6375(7) 0.066(5) Uani 1 1 d . . . F54 F 0.1432(7) 1.3556(3) 0.6103(5) 0.118(4) Uani 1 1 d . . . C55 C 0.1831(9) 1.2760(6) 0.6210(6) 0.059(4) Uani 1 1 d . . . F55 F 0.1119(6) 1.2650(3) 0.5797(4) 0.096(3) Uani 1 1 d . . . C56 C 0.2400(9) 1.2417(5) 0.6478(6) 0.045(3) Uani 1 1 d . . . F56 F 0.2202(5) 1.1965(3) 0.6285(3) 0.062(2) Uani 1 1 d . . . S6 S 0.3751(2) 1.11360(10) 0.83660(14) 0.0409(8) Uani 1 1 d . . . C61 C 0.3811(7) 1.1524(3) 0.8965(5) 0.028(3) Uani 1 1 d . . . C62 C 0.3289(8) 1.1459(4) 0.9395(5) 0.038(3) Uani 1 1 d . . . F62 F 0.2674(5) 1.1129(3) 0.9340(3) 0.064(2) Uani 1 1 d . . . C63 C 0.3438(9) 1.1723(5) 0.9918(6) 0.045(3) Uani 1 1 d . . . F63 F 0.2962(5) 1.1638(3) 1.0355(3) 0.072(2) Uani 1 1 d . . . C64 C 0.4072(10) 1.2060(5) 1.0003(6) 0.052(4) Uani 1 1 d . . . F64 F 0.4200(6) 1.2326(2) 1.0493(3) 0.071(2) Uani 1 1 d . . . C65 C 0.4594(9) 1.2140(4) 0.9576(7) 0.048(4) Uani 1 1 d . . . F65 F 0.5241(5) 1.2465(2) 0.9652(3) 0.067(2) Uani 1 1 d . . . C66 C 0.4465(8) 1.1882(4) 0.9066(5) 0.033(3) Uani 1 1 d . . . F66 F 0.4977(4) 1.1965(2) 0.8658(3) 0.0502(19) Uani 1 1 d . . . S7 S 0.2039(2) 1.20503(11) 0.83191(15) 0.0483(9) Uani 1 1 d . . . C71 C 0.1324(9) 1.2420(4) 0.7832(5) 0.040(3) Uani 1 1 d . . . C72 C 0.0577(10) 1.2257(4) 0.7459(6) 0.050(4) Uani 1 1 d . . . F72 F 0.0394(5) 1.1795(3) 0.7422(3) 0.065(2) Uani 1 1 d . . . C73 C -0.0004(11) 1.2549(6) 0.7083(7) 0.068(4) Uani 1 1 d . . . F73 F -0.0716(6) 1.2362(3) 0.6726(4) 0.093(3) Uani 1 1 d . . . C74 C 0.0135(11) 1.3014(6) 0.7112(8) 0.074(5) Uani 1 1 d . . . F74 F -0.0419(7) 1.3314(3) 0.6776(5) 0.118(4) Uani 1 1 d . . . C75 C 0.0871(11) 1.3201(5) 0.7479(7) 0.067(4) Uani 1 1 d . . . F75 F 0.1021(7) 1.3660(3) 0.7501(5) 0.108(3) Uani 1 1 d . . . C76 C 0.1468(10) 1.2899(5) 0.7849(7) 0.055(4) Uani 1 1 d . . . F76 F 0.2172(6) 1.3087(3) 0.8196(4) 0.080(3) Uani 1 1 d . . . S8 S 0.1600(2) 1.06269(10) 0.79336(14) 0.0354(8) Uani 1 1 d . . . C81 C 0.0882(7) 1.0309(4) 0.7377(5) 0.029(3) Uani 1 1 d . . . C82 C 0.0656(8) 0.9853(4) 0.7493(6) 0.041(3) Uani 1 1 d . . . F82 F 0.0997(5) 0.9644(2) 0.8010(3) 0.054(2) Uani 1 1 d . . . C83 C 0.0090(8) 0.9589(4) 0.7081(6) 0.046(3) Uani 1 1 d . . . F83 F -0.0104(5) 0.9145(2) 0.7205(3) 0.070(2) Uani 1 1 d . . . C84 C -0.0284(8) 0.9785(4) 0.6534(6) 0.043(3) Uani 1 1 d . . . F84 F -0.0819(5) 0.9526(2) 0.6143(3) 0.067(2) Uani 1 1 d . . . C85 C -0.0057(8) 1.0241(4) 0.6424(5) 0.036(3) Uani 1 1 d . . . F85 F -0.0385(5) 1.0421(2) 0.5894(3) 0.058(2) Uani 1 1 d . . . C86 C 0.0497(7) 1.0493(4) 0.6830(5) 0.032(3) Uani 1 1 d . . . F86 F 0.0700(4) 1.0939(2) 0.6701(3) 0.0454(18) Uani 1 1 d . . . S9 S -0.0807(2) 1.08468(11) 0.78595(14) 0.0432(8) Uani 1 1 d . . . C91 C -0.1714(8) 1.0936(4) 0.8220(5) 0.030(3) Uani 1 1 d . . . C92 C -0.2052(8) 1.0591(4) 0.8538(5) 0.035(3) Uani 1 1 d . . . F92 F -0.1717(5) 1.0157(2) 0.8561(3) 0.0516(19) Uani 1 1 d . . . C93 C -0.2766(8) 1.0672(4) 0.8839(5) 0.039(3) Uani 1 1 d . . . F93 F -0.3069(5) 1.0317(2) 0.9141(3) 0.060(2) Uani 1 1 d . . . C94 C -0.3151(7) 1.1103(4) 0.8822(5) 0.034(3) Uani 1 1 d . . . F94 F -0.3853(4) 1.1171(2) 0.9101(3) 0.056(2) Uani 1 1 d . . . C95 C -0.2873(7) 1.1457(4) 0.8488(5) 0.035(3) Uani 1 1 d . . . F95 F -0.3244(5) 1.1882(2) 0.8470(3) 0.0528(19) Uani 1 1 d . . . C96 C -0.2172(8) 1.1366(4) 0.8185(5) 0.039(3) Uani 1 1 d . . . F96 F -0.1909(4) 1.1724(2) 0.7873(3) 0.0456(18) Uani 1 1 d . . . S10 S -0.0598(2) 1.15998(10) 0.92770(14) 0.0397(8) Uani 1 1 d . . . C101 C 0.0002(9) 1.2133(4) 0.9270(5) 0.040(3) Uani 1 1 d . . . C102 C 0.0821(10) 1.2182(5) 0.9603(7) 0.053(4) Uani 1 1 d . . . F102 F 0.1203(6) 1.1835(3) 0.9955(4) 0.082(3) Uani 1 1 d . . . C103 C 0.1313(11) 1.2608(5) 0.9612(8) 0.072(5) Uani 1 1 d . . . F103 F 0.2123(6) 1.2639(3) 0.9950(5) 0.114(4) Uani 1 1 d . . . C104 C 0.0970(13) 1.2973(5) 0.9290(8) 0.074(5) Uani 1 1 d . . . F104 F 0.1410(7) 1.3377(3) 0.9290(5) 0.115(4) Uani 1 1 d . . . C105 C 0.0104(13) 1.2927(5) 0.8925(7) 0.065(5) Uani 1 1 d . . . F105 F -0.0242(8) 1.3290(3) 0.8606(4) 0.101(4) Uani 1 1 d . . . C106 C -0.0356(10) 1.2503(5) 0.8918(6) 0.049(4) Uani 1 1 d . . . F106 F -0.1164(6) 1.2487(2) 0.8592(4) 0.076(3) Uani 1 1 d . . . S11 S 0.0430(3) 1.03823(11) 0.92633(17) 0.0803(15) Uani 1 1 d . . . C111 C 0.0654(10) 1.0577(3) 0.9947(4) 0.063(5) Uani 1 1 d G . . C112 C -0.0090(8) 1.0675(4) 1.0207(6) 0.104(7) Uani 1 1 d GD . . F112 F -0.0943(9) 1.0628(4) 0.9965(6) 0.168(7) Uani 1 1 d D . . C113 C 0.0025(9) 1.0827(4) 1.0790(6) 0.19(2) Uani 1 1 d GD . . F113 F -0.0740(13) 1.0866(4) 1.1042(7) 0.258(12) Uani 1 1 d D . . C114 C 0.0884(11) 1.0881(4) 1.1114(4) 0.20(2) Uani 1 1 d GD . . F114 F 0.0764(15) 1.1020(4) 1.1737(6) 0.250(11) Uani 1 1 d D . . C115 C 0.1628(8) 1.0783(5) 1.0854(6) 0.20(2) Uani 1 1 d GD . . F115 F 0.2303(11) 1.0861(5) 1.1265(8) 0.332(18) Uani 1 1 d D . . C116 C 0.1513(8) 1.0631(4) 1.0271(6) 0.143(15) Uani 1 1 d GD . . F116 F 0.2193(8) 1.0495(5) 1.0066(7) 0.166(7) Uani 1 1 d D . . C916 C 0.2954(10) 0.9795(5) 0.9076(8) 0.069(5) Uani 1 1 d . . . H10A H 0.2363 0.9842 0.9154 0.083 Uiso 1 1 calc R . . N911 N 0.3183(9) 0.9953(3) 0.8574(5) 0.059(3) Uani 1 1 d . . . H11A H 0.2780 1.0101 0.8317 0.071 Uiso 1 1 calc R . . C912 C 0.4433(10) 0.9502(4) 0.9362(6) 0.051(4) Uani 1 1 d . . . C914 C 0.3994(11) 0.9893(5) 0.8453(6) 0.060(4) Uani 1 1 d . . . H10B H 0.4134 1.0002 0.8088 0.072 Uiso 1 1 calc R . . C915 C 0.3583(12) 0.9564(5) 0.9479(6) 0.074(5) Uani 1 1 d . . . H10C H 0.3429 0.9448 0.9837 0.089 Uiso 1 1 calc R . . C913 C 0.4634(10) 0.9673(4) 0.8852(7) 0.057(4) Uani 1 1 d . . . H10D H 0.5225 0.9640 0.8770 0.068 Uiso 1 1 calc R . . N921 N -0.0267(9) 0.8422(4) 0.5856(6) 0.062(3) Uani 1 1 d . . . N901 N -0.1158(8) 0.8228(4) 0.6713(5) 0.060(3) Uani 1 1 d . . . C922 C 0.0781(11) 0.8477(4) 0.4957(7) 0.059(4) Uani 1 1 d . . . C906 C -0.1797(10) 0.8483(5) 0.6883(7) 0.070(5) Uani 1 1 d . . . H90A H -0.1982 0.8761 0.6668 0.084 Uiso 1 1 calc R . . C904 C -0.0904(10) 0.7848(5) 0.7015(7) 0.063(4) Uani 1 1 d . . . H90B H -0.0462 0.7654 0.6889 0.075 Uiso 1 1 calc R . . C924 C -0.0621(11) 0.8525(4) 0.5299(9) 0.070(5) Uani 1 1 d . . . H80A H -0.1252 0.8570 0.5211 0.084 Uiso 1 1 calc R . . C923 C -0.0151(11) 0.8571(4) 0.4843(7) 0.066(4) Uani 1 1 d . . . H80B H -0.0443 0.8665 0.4460 0.079 Uiso 1 1 calc R . . C925 C 0.1144(11) 0.8381(5) 0.5518(7) 0.063(4) Uani 1 1 d . . . H80C H 0.1773 0.8332 0.5620 0.075 Uiso 1 1 calc R . . C903 C -0.1255(11) 0.7714(5) 0.7518(7) 0.070(5) Uani 1 1 d . . . H90C H -0.1032 0.7441 0.7734 0.085 Uiso 1 1 calc R . . C905 C -0.2220(11) 0.8369(6) 0.7362(9) 0.089(6) Uani 1 1 d . . . H90D H -0.2698 0.8557 0.7450 0.106 Uiso 1 1 calc R . . C921 C 0.1337(11) 0.8524(5) 0.4472(7) 0.083(5) Uani 1 1 d . . . H80D H 0.1974 0.8489 0.4642 0.124 Uiso 1 1 calc R . . H80E H 0.1236 0.8834 0.4288 0.124 Uiso 1 1 calc R . . H80F H 0.1162 0.8280 0.4174 0.124 Uiso 1 1 calc R . . C926 C 0.0610(12) 0.8352(5) 0.5958(8) 0.073(5) Uani 1 1 d . . . H80G H 0.0892 0.8280 0.6350 0.088 Uiso 1 1 calc R . . C902 C -0.1937(11) 0.7984(6) 0.7701(8) 0.078(5) Uani 1 1 d . . . C911 C 0.5112(12) 0.9241(5) 0.9803(8) 0.113(7) Uani 1 1 d . . . H10E H 0.5709 0.9275 0.9696 0.170 Uiso 1 1 calc R . . H10F H 0.4951 0.8907 0.9800 0.170 Uiso 1 1 calc R . . H10G H 0.5119 0.9370 1.0199 0.170 Uiso 1 1 calc R . . C901 C -0.2338(14) 0.7857(7) 0.8241(9) 0.147(9) Uani 1 1 d . . . H90E H -0.2923 0.8010 0.8218 0.220 Uiso 1 1 calc R . . H90F H -0.1936 0.7963 0.8599 0.220 Uiso 1 1 calc R . . H90G H -0.2414 0.7516 0.8258 0.220 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0308(3) 0.0335(2) 0.0341(3) 0.0004(2) 0.0049(2) -0.0014(2) Bi2 0.0311(3) 0.0396(3) 0.0307(3) -0.0025(2) 0.0015(2) 0.0046(2) Bi3 0.0302(3) 0.0349(3) 0.0410(3) -0.0068(2) 0.0043(2) 0.0013(2) S1 0.0300(18) 0.0425(18) 0.044(2) -0.0109(15) 0.0007(14) 0.0033(14) C1 0.027(8) 0.039(7) 0.047(9) -0.007(6) -0.011(6) -0.009(6) C2 0.043(9) 0.046(8) 0.037(9) -0.008(6) 0.010(7) -0.010(7) F2 0.046(5) 0.071(5) 0.049(5) 0.013(4) -0.001(4) -0.013(4) C3 0.063(12) 0.035(8) 0.082(13) 0.004(8) -0.035(9) 0.014(8) F3 0.078(7) 0.060(5) 0.105(8) 0.025(5) -0.024(5) 0.000(5) C4 0.027(9) 0.058(10) 0.071(12) -0.028(8) -0.010(7) 0.019(7) F4 0.072(7) 0.079(6) 0.104(8) -0.023(5) -0.020(5) 0.039(5) C5 0.040(10) 0.070(10) 0.053(11) -0.021(8) 0.004(7) 0.003(8) F5 0.048(6) 0.141(8) 0.060(6) -0.018(5) 0.011(5) 0.032(5) C6 0.043(9) 0.044(8) 0.053(10) 0.003(7) 0.010(7) 0.008(7) F6 0.050(5) 0.079(5) 0.065(6) 0.007(4) 0.020(4) -0.002(4) S2 0.047(3) 0.097(3) 0.096(4) 0.049(3) 0.032(2) 0.007(2) C21 0.043(9) 0.057(9) 0.045(10) 0.028(7) 0.009(7) -0.005(7) F21 0.104(8) 0.047(5) 0.092(7) -0.015(4) 0.022(5) -0.017(5) C22 0.062(11) 0.056(10) 0.049(10) 0.012(8) 0.024(8) -0.021(8) C23 0.060(11) 0.069(11) 0.040(10) 0.008(8) 0.002(8) -0.017(9) F23 0.083(8) 0.117(7) 0.079(7) 0.003(5) -0.014(6) -0.026(6) C24 0.067(12) 0.038(9) 0.065(11) 0.016(8) 0.029(9) 0.008(8) F24 0.081(7) 0.077(6) 0.106(8) 0.037(5) 0.023(6) 0.028(5) C25 0.107(15) 0.023(8) 0.065(12) 0.005(8) 0.036(10) -0.011(9) F25 0.132(9) 0.047(5) 0.112(8) -0.012(5) 0.051(7) -0.010(5) C26 0.065(12) 0.048(9) 0.054(11) 0.009(8) 0.009(9) -0.020(8) F26 0.095(8) 0.122(7) 0.065(7) -0.006(5) 0.012(6) -0.053(6) S3 0.081(3) 0.0381(19) 0.038(2) -0.0021(15) 0.0053(19) 0.0112(18) C31 0.032(8) 0.046(7) 0.036(8) -0.008(6) 0.011(6) 0.012(6) C32 0.039(10) 0.056(9) 0.094(14) -0.016(8) 0.021(9) 0.007(7) F32 0.046(6) 0.097(7) 0.126(9) -0.027(6) 0.018(6) 0.008(5) C33 0.135(19) 0.047(9) 0.114(18) -0.017(11) 0.117(16) -0.009(11) F33 0.139(10) 0.087(7) 0.176(11) -0.021(6) 0.126(9) -0.002(6) C34 0.21(3) 0.040(9) 0.026(11) -0.008(7) 0.045(14) 0.012(13) F34 0.287(16) 0.069(6) 0.068(7) 0.000(5) 0.095(9) 0.016(7) C35 0.097(15) 0.055(10) 0.046(12) -0.013(8) 0.011(11) 0.012(9) F35 0.179(12) 0.090(7) 0.059(7) -0.019(5) -0.049(7) 0.029(7) C36 0.044(9) 0.036(7) 0.032(9) -0.009(6) 0.013(7) -0.003(6) F36 0.050(6) 0.080(6) 0.086(7) -0.015(4) 0.003(5) 0.000(4) S4 0.0287(18) 0.0369(17) 0.030(2) -0.0039(13) 0.0020(14) -0.0023(13) C41 0.014(6) 0.034(7) 0.032(8) -0.005(5) 0.010(5) 0.000(5) C42 0.046(8) 0.017(6) 0.033(8) -0.005(5) 0.009(6) 0.006(5) F42 0.045(5) 0.038(4) 0.042(5) 0.000(3) -0.003(3) -0.004(3) C43 0.032(8) 0.033(7) 0.040(9) -0.006(6) -0.002(6) 0.004(6) F43 0.059(5) 0.062(5) 0.032(5) -0.001(3) -0.015(4) 0.002(4) C44 0.030(8) 0.044(8) 0.042(9) -0.021(6) 0.005(6) -0.001(6) F44 0.063(6) 0.062(5) 0.062(6) -0.029(4) -0.011(4) -0.014(4) C45 0.033(8) 0.028(7) 0.040(9) -0.007(6) 0.010(6) -0.002(6) F45 0.076(6) 0.035(4) 0.067(6) -0.002(4) 0.010(4) -0.015(4) C46 0.041(8) 0.036(7) 0.028(8) -0.013(6) 0.007(6) 0.000(6) F46 0.052(5) 0.047(4) 0.038(5) 0.007(3) -0.002(4) -0.001(3) S5 0.034(2) 0.0381(18) 0.042(2) -0.0021(14) -0.0038(15) 0.0002(14) C51 0.034(8) 0.033(7) 0.037(8) 0.008(6) 0.001(6) 0.009(6) C52 0.060(11) 0.043(9) 0.055(10) 0.004(7) 0.006(8) 0.011(8) F52 0.076(7) 0.045(5) 0.087(7) -0.014(4) -0.001(5) -0.010(4) C53 0.094(14) 0.037(9) 0.083(13) 0.008(9) 0.022(11) 0.005(9) F53 0.110(9) 0.047(6) 0.152(10) 0.010(5) 0.021(7) 0.011(5) C54 0.069(12) 0.067(11) 0.062(12) 0.034(9) 0.007(9) 0.018(9) F54 0.110(9) 0.098(7) 0.144(10) 0.050(7) 0.020(7) 0.061(6) C55 0.049(10) 0.087(12) 0.031(9) 0.024(8) -0.022(7) -0.004(8) F55 0.069(7) 0.144(8) 0.064(7) 0.021(5) -0.025(5) 0.018(6) C56 0.042(9) 0.055(9) 0.038(9) 0.020(7) 0.007(7) 0.002(7) F56 0.064(6) 0.063(5) 0.050(5) 0.003(4) -0.017(4) -0.008(4) S6 0.047(2) 0.0358(18) 0.035(2) -0.0069(14) -0.0056(15) 0.0084(15) C61 0.026(7) 0.026(6) 0.028(7) 0.002(5) -0.012(5) 0.008(5) C62 0.032(8) 0.034(7) 0.042(9) 0.005(6) -0.006(6) -0.002(6) F62 0.059(6) 0.080(5) 0.051(5) 0.012(4) -0.002(4) -0.025(4) C63 0.032(8) 0.071(10) 0.029(9) 0.006(7) 0.003(6) 0.015(7) F63 0.056(6) 0.131(7) 0.031(5) 0.009(4) 0.014(4) 0.018(5) C64 0.056(10) 0.063(9) 0.027(9) -0.011(7) -0.017(7) 0.032(8) F64 0.084(7) 0.077(5) 0.045(5) -0.025(4) -0.008(4) 0.024(5) C65 0.043(9) 0.029(7) 0.067(11) -0.003(7) -0.005(8) -0.001(6) F65 0.070(6) 0.035(4) 0.084(6) -0.007(4) -0.019(5) -0.009(4) C66 0.027(7) 0.036(7) 0.037(8) 0.015(6) 0.006(6) 0.006(6) F66 0.036(5) 0.063(5) 0.050(5) 0.016(4) 0.004(4) -0.003(3) S7 0.054(2) 0.052(2) 0.037(2) -0.0062(16) 0.0050(17) 0.0178(17) C71 0.041(9) 0.036(7) 0.045(9) 0.001(6) 0.017(7) 0.003(6) C72 0.058(10) 0.032(8) 0.063(11) 0.012(7) 0.019(8) 0.010(7) F72 0.056(6) 0.065(5) 0.069(6) 0.008(4) -0.003(4) 0.000(4) C73 0.057(12) 0.079(12) 0.069(12) 0.012(10) 0.013(9) 0.009(9) F73 0.060(7) 0.112(7) 0.091(8) 0.019(5) -0.027(5) -0.003(5) C74 0.059(12) 0.064(11) 0.101(15) 0.026(10) 0.017(10) 0.032(10) F74 0.101(9) 0.100(7) 0.145(10) 0.054(7) 0.001(7) 0.044(6) C75 0.068(12) 0.045(9) 0.087(13) 0.007(9) 0.015(10) -0.004(8) F75 0.137(10) 0.046(5) 0.144(10) 0.019(5) 0.034(7) 0.004(5) C76 0.047(10) 0.049(9) 0.070(12) 0.002(8) 0.016(8) 0.001(8) F76 0.090(8) 0.067(5) 0.081(7) -0.016(5) 0.010(5) -0.014(5) S8 0.0267(18) 0.0407(18) 0.038(2) -0.0027(14) 0.0040(14) 0.0032(14) C81 0.028(7) 0.033(7) 0.026(7) -0.013(5) 0.006(5) 0.003(5) C82 0.035(8) 0.050(8) 0.042(9) 0.000(7) 0.016(7) 0.001(6) F82 0.066(6) 0.049(4) 0.043(5) 0.005(4) -0.004(4) -0.011(4) C83 0.035(8) 0.041(8) 0.061(11) -0.018(7) 0.005(7) -0.006(6) F83 0.078(6) 0.046(5) 0.080(6) -0.007(4) -0.005(5) -0.019(4) C84 0.030(8) 0.053(9) 0.044(9) -0.017(7) 0.003(6) 0.002(6) F84 0.068(6) 0.067(5) 0.063(6) -0.025(4) -0.001(4) -0.013(4) C85 0.030(7) 0.047(8) 0.026(8) -0.001(6) -0.006(6) 0.010(6) F85 0.061(6) 0.069(5) 0.041(5) -0.006(4) -0.004(4) 0.009(4) C86 0.025(7) 0.040(7) 0.029(8) -0.005(6) 0.004(6) 0.008(6) F86 0.048(5) 0.042(4) 0.044(5) -0.002(3) 0.003(4) 0.004(3) S9 0.032(2) 0.059(2) 0.039(2) -0.0101(16) 0.0072(15) 0.0000(16) C91 0.036(8) 0.028(7) 0.022(7) -0.001(5) -0.008(5) -0.003(5) C92 0.035(8) 0.035(7) 0.030(8) 0.001(6) -0.010(6) 0.002(6) F92 0.043(5) 0.045(4) 0.063(5) 0.005(4) 0.000(4) 0.001(4) C93 0.028(8) 0.046(8) 0.042(9) 0.000(6) -0.002(6) -0.011(6) F93 0.050(5) 0.068(5) 0.066(6) 0.012(4) 0.017(4) -0.010(4) C94 0.023(7) 0.053(8) 0.027(7) -0.009(6) 0.007(5) 0.002(6) F94 0.030(4) 0.081(5) 0.060(5) -0.006(4) 0.020(4) -0.002(4) C95 0.023(7) 0.046(7) 0.033(8) -0.006(6) -0.007(5) 0.001(6) F95 0.048(5) 0.052(4) 0.059(5) -0.005(4) 0.011(4) 0.017(4) C96 0.039(8) 0.044(8) 0.031(8) -0.006(6) -0.001(6) -0.012(6) F96 0.049(5) 0.045(4) 0.043(5) 0.009(3) 0.008(4) -0.001(3) S10 0.041(2) 0.0412(18) 0.040(2) -0.0052(14) 0.0155(15) -0.0011(15) C101 0.044(9) 0.043(8) 0.035(8) -0.008(6) 0.008(7) 0.015(6) C102 0.048(10) 0.045(9) 0.069(11) -0.012(8) 0.014(8) 0.002(8) F102 0.069(6) 0.054(5) 0.107(8) -0.009(5) -0.032(5) 0.013(4) C103 0.045(11) 0.058(10) 0.126(16) -0.051(10) 0.046(10) -0.004(9) F103 0.043(6) 0.079(6) 0.214(13) -0.052(6) 0.007(7) -0.010(5) C104 0.079(14) 0.038(9) 0.123(17) -0.016(10) 0.066(12) 0.007(10) F104 0.142(10) 0.039(5) 0.192(11) -0.039(6) 0.103(8) -0.030(5) C105 0.090(14) 0.053(10) 0.063(12) 0.004(8) 0.046(10) 0.013(10) F105 0.191(11) 0.046(5) 0.075(7) 0.012(5) 0.049(7) 0.004(6) C106 0.055(10) 0.050(9) 0.045(10) -0.007(7) 0.016(8) -0.003(8) F106 0.090(8) 0.056(5) 0.071(7) 0.003(4) -0.014(5) 0.011(5) S11 0.153(5) 0.030(2) 0.047(3) 0.0016(17) -0.013(3) 0.001(2) C111 0.103(15) 0.046(9) 0.052(11) 0.018(7) 0.043(10) 0.016(9) C112 0.14(2) 0.041(10) 0.13(2) 0.034(11) 0.007(18) 0.006(13) F112 0.167(14) 0.115(9) 0.258(18) 0.108(11) 0.139(13) 0.048(10) C113 0.44(6) 0.030(10) 0.18(3) 0.007(14) 0.26(4) 0.041(18) F113 0.51(3) 0.136(11) 0.181(16) 0.090(11) 0.22(2) 0.154(17) C114 0.41(5) 0.076(15) 0.045(15) 0.031(11) -0.12(2) -0.10(2) F114 0.53(4) 0.128(10) 0.102(12) -0.030(9) 0.100(17) -0.055(15) C115 0.15(3) 0.15(3) 0.32(5) 0.20(3) 0.06(3) 0.01(2) F115 0.38(3) 0.167(13) 0.33(2) 0.191(15) -0.27(2) -0.179(17) C116 0.32(4) 0.037(11) 0.040(13) 0.019(9) -0.06(2) -0.039(19) F116 0.083(10) 0.159(12) 0.247(18) 0.149(12) 0.005(9) -0.005(8) C916 0.046(11) 0.076(11) 0.089(14) -0.005(10) 0.025(10) 0.012(8) N911 0.061(9) 0.042(7) 0.063(10) 0.008(6) -0.018(7) 0.006(6) C912 0.062(11) 0.044(8) 0.039(9) 0.001(7) -0.017(8) 0.009(7) C914 0.062(12) 0.076(11) 0.039(10) 0.002(7) 0.000(8) -0.014(9) C915 0.095(15) 0.083(11) 0.043(11) 0.027(8) 0.007(10) 0.029(10) C913 0.048(10) 0.051(9) 0.068(12) 0.013(8) 0.003(8) 0.000(7) N921 0.065(10) 0.040(7) 0.074(10) -0.005(6) -0.008(7) -0.007(6) N901 0.048(8) 0.032(6) 0.094(10) -0.024(6) -0.002(7) 0.013(6) C922 0.070(12) 0.039(8) 0.074(12) 0.011(8) 0.028(9) 0.002(8) C906 0.061(12) 0.041(9) 0.096(14) -0.005(8) -0.023(10) 0.005(8) C904 0.057(11) 0.043(9) 0.089(13) -0.038(8) 0.018(9) 0.001(8) C924 0.057(11) 0.029(8) 0.119(16) 0.015(9) -0.004(11) 0.003(7) C923 0.061(12) 0.037(8) 0.096(13) 0.023(8) 0.005(10) 0.004(8) C925 0.056(11) 0.065(10) 0.063(12) -0.005(8) 0.001(9) -0.008(8) C903 0.059(12) 0.059(10) 0.090(14) -0.010(9) 0.005(10) 0.002(8) C905 0.051(12) 0.084(13) 0.140(19) -0.001(12) 0.042(12) -0.004(9) C921 0.093(14) 0.062(10) 0.092(14) 0.011(9) 0.013(11) 0.006(9) C926 0.060(12) 0.067(10) 0.086(14) -0.006(9) -0.009(10) -0.012(9) C902 0.049(11) 0.079(12) 0.112(16) 0.008(11) 0.029(10) -0.011(9) C911 0.117(17) 0.080(12) 0.113(16) 0.036(11) -0.065(13) 0.020(11) C901 0.12(2) 0.152(19) 0.19(2) 0.029(16) 0.088(18) -0.045(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 S3 2.575(3) . ? Bi1 S1 2.576(3) . ? Bi1 S2 2.640(4) . ? Bi1 S4 2.973(3) . ? Bi2 S6 2.542(3) . ? Bi2 S7 2.728(3) . ? Bi2 S5 2.733(3) . ? Bi2 S4 2.896(3) . ? Bi2 S8 2.980(3) . ? Bi3 S11 2.553(4) . ? Bi3 S9 2.578(3) . ? Bi3 S10 2.642(3) . ? Bi3 S8 2.996(3) . ? S1 C1 1.759(12) . ? C1 C6 1.398(17) . ? C1 C2 1.404(15) . ? C2 F2 1.339(13) . ? C2 C3 1.376(17) . ? C3 F3 1.326(15) . ? C3 C4 1.39(2) . ? C4 F4 1.333(13) . ? C4 C5 1.370(19) . ? C5 F5 1.343(15) . ? C5 C6 1.361(17) . ? C6 F6 1.338(13) . ? S2 C21 1.759(13) . ? C21 C22 1.371(18) . ? C21 C26 1.410(17) . ? F21 C22 1.346(14) . ? C22 C23 1.365(19) . ? C23 F23 1.336(15) . ? C23 C24 1.342(18) . ? C24 F24 1.363(15) . ? C24 C25 1.39(2) . ? C25 F25 1.322(14) . ? C25 C26 1.350(19) . ? C26 F26 1.369(15) . ? S3 C31 1.762(12) . ? C31 C36 1.380(16) . ? C31 C32 1.401(17) . ? C32 F32 1.339(16) . ? C32 C33 1.35(2) . ? C33 F33 1.372(18) . ? C33 C34 1.39(3) . ? C34 F34 1.339(17) . ? C34 C35 1.37(3) . ? C35 C36 1.336(18) . ? C35 F35 1.340(18) . ? C36 F36 1.339(13) . ? S4 C41 1.752(11) . ? C41 C42 1.393(14) . ? C41 C46 1.396(14) . ? C42 F42 1.358(11) . ? C42 C43 1.374(15) . ? C43 F43 1.327(12) . ? C43 C44 1.379(15) . ? C44 F44 1.341(12) . ? C44 C45 1.386(16) . ? C45 F45 1.340(11) . ? C45 C46 1.371(15) . ? C46 F46 1.341(12) . ? S5 C51 1.776(11) . ? C51 C56 1.360(16) . ? C51 C52 1.382(16) . ? C52 F52 1.338(15) . ? C52 C53 1.371(18) . ? C53 C54 1.34(2) . ? C53 F53 1.358(15) . ? C54 F54 1.352(15) . ? C54 C55 1.379(18) . ? C55 F55 1.344(15) . ? C55 C56 1.377(17) . ? C56 F56 1.377(13) . ? S6 C61 1.753(11) . ? C61 C62 1.379(15) . ? C61 C66 1.411(15) . ? C62 F62 1.313(12) . ? C62 C63 1.401(16) . ? C63 C64 1.346(18) . ? C63 F63 1.354(13) . ? C64 F64 1.342(13) . ? C64 C65 1.379(18) . ? C65 F65 1.338(13) . ? C65 C66 1.366(16) . ? C66 F66 1.335(12) . ? S7 C71 1.765(13) . ? C71 C72 1.375(18) . ? C71 C76 1.379(16) . ? C72 F72 1.342(13) . ? C72 C73 1.397(19) . ? C73 C74 1.342(19) . ? C73 F73 1.344(17) . ? C74 F74 1.342(15) . ? C74 C75 1.38(2) . ? C75 F75 1.327(14) . ? C75 C76 1.419(19) . ? C76 F76 1.327(15) . ? S8 C81 1.776(11) . ? C81 C82 1.379(14) . ? C81 C86 1.391(15) . ? C82 F82 1.349(13) . ? C82 C83 1.383(16) . ? C83 F83 1.340(13) . ? C83 C84 1.400(17) . ? C84 F84 1.323(13) . ? C84 C85 1.379(15) . ? C85 F85 1.334(12) . ? C85 C86 1.347(15) . ? C86 F86 1.354(12) . ? S9 C91 1.739(12) . ? C91 C92 1.373(15) . ? C91 C96 1.405(15) . ? C92 F92 1.336(11) . ? C92 C93 1.396(16) . ? C93 F93 1.351(12) . ? C93 C94 1.356(15) . ? C94 F94 1.346(12) . ? C94 C95 1.377(15) . ? C95 F95 1.329(12) . ? C95 C96 1.390(15) . ? C96 F96 1.343(12) . ? S10 C101 1.770(13) . ? C101 C102 1.347(17) . ? C101 C106 1.380(17) . ? C102 F102 1.342(15) . ? C102 C103 1.422(18) . ? C103 C104 1.33(2) . ? C103 F103 1.335(18) . ? C104 F104 1.327(16) . ? C104 C105 1.43(2) . ? C105 F105 1.322(16) . ? C105 C106 1.392(18) . ? C106 F106 1.319(15) . ? S11 C111 1.642(9) . ? C111 C112 1.3900 . ? C111 C116 1.3900 . ? C112 F112 1.321(13) . ? C112 C113 1.3900 . ? C113 F113 1.385(14) . ? C113 C114 1.3900 . ? C114 C115 1.3900 . ? C114 F114 1.523(10) . ? C115 F115 1.283(13) . ? C115 C116 1.3900 . ? C116 F116 1.262(13) . ? C916 N911 1.338(17) . ? C916 C915 1.374(19) . ? N911 C914 1.315(17) . ? C912 C913 1.350(18) . ? C912 C915 1.369(19) . ? C912 C911 1.509(17) . ? C914 C913 1.364(18) . ? N921 C926 1.321(18) . ? N921 C924 1.331(17) . ? N901 C904 1.306(16) . ? N901 C906 1.322(17) . ? C922 C925 1.338(18) . ? C922 C923 1.414(19) . ? C922 C921 1.512(18) . ? C906 C905 1.40(2) . ? C904 C903 1.403(19) . ? C924 C923 1.369(19) . ? C925 C926 1.40(2) . ? C903 C902 1.409(19) . ? C905 C902 1.37(2) . ? C902 C901 1.51(2) . ? 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 S3 Bi1 S1 94.29(10) . . ? S3 Bi1 S2 98.23(13) . . ? S1 Bi1 S2 94.97(13) . . ? S3 Bi1 S4 78.12(10) . . ? S1 Bi1 S4 80.14(9) . . ? S2 Bi1 S4 173.58(11) . . ? S6 Bi2 S7 87.96(10) . . ? S6 Bi2 S5 87.77(11) . . ? S7 Bi2 S5 91.48(11) . . ? S6 Bi2 S4 71.84(9) . . ? S7 Bi2 S4 159.71(9) . . ? S5 Bi2 S4 89.65(9) . . ? S6 Bi2 S8 79.42(10) . . ? S7 Bi2 S8 94.00(10) . . ? S5 Bi2 S8 165.86(9) . . ? S4 Bi2 S8 80.74(9) . . ? S11 Bi3 S9 91.64(12) . . ? S11 Bi3 S10 94.11(13) . . ? S9 Bi3 S10 95.43(11) . . ? S11 Bi3 S8 87.36(12) . . ? S9 Bi3 S8 81.96(10) . . ? S10 Bi3 S8 177.05(10) . . ? C1 S1 Bi1 104.8(4) . . ? C6 C1 C2 116.0(11) . . ? C6 C1 S1 121.3(9) . . ? C2 C1 S1 122.7(10) . . ? F2 C2 C3 119.7(13) . . ? F2 C2 C1 118.2(11) . . ? C3 C2 C1 122.0(13) . . ? F3 C3 C2 119.0(16) . . ? F3 C3 C4 122.1(13) . . ? C2 C3 C4 118.9(13) . . ? F4 C4 C5 121.7(15) . . ? F4 C4 C3 117.5(14) . . ? C5 C4 C3 120.8(12) . . ? F5 C5 C6 121.2(14) . . ? F5 C5 C4 119.5(13) . . ? C6 C5 C4 119.4(14) . . ? F6 C6 C5 116.8(13) . . ? F6 C6 C1 120.3(11) . . ? C5 C6 C1 122.9(13) . . ? C21 S2 Bi1 91.5(4) . . ? C22 C21 C26 113.9(13) . . ? C22 C21 S2 125.3(12) . . ? C26 C21 S2 120.8(12) . . ? F21 C22 C23 118.2(14) . . ? F21 C22 C21 118.2(14) . . ? C23 C22 C21 123.5(14) . . ? F23 C23 C24 119.4(16) . . ? F23 C23 C22 120.2(14) . . ? C24 C23 C22 120.4(15) . . ? C23 C24 F24 122.0(16) . . ? C23 C24 C25 119.7(14) . . ? F24 C24 C25 118.2(14) . . ? F25 C25 C26 121.6(17) . . ? F25 C25 C24 119.7(16) . . ? C26 C25 C24 118.6(13) . . ? C25 C26 F26 117.1(14) . . ? C25 C26 C21 123.8(14) . . ? F26 C26 C21 119.1(14) . . ? C31 S3 Bi1 103.5(4) . . ? C36 C31 C32 116.1(13) . . ? C36 C31 S3 121.8(10) . . ? C32 C31 S3 122.1(11) . . ? F32 C32 C33 119.5(16) . . ? F32 C32 C31 118.7(15) . . ? C33 C32 C31 121.6(16) . . ? C32 C33 F33 118(2) . . ? C32 C33 C34 120.2(17) . . ? F33 C33 C34 122(2) . . ? F34 C34 C35 125(2) . . ? F34 C34 C33 116(2) . . ? C35 C34 C33 118.7(16) . . ? C36 C35 F35 123.6(17) . . ? C36 C35 C34 120.7(17) . . ? F35 C35 C34 115.6(17) . . ? C35 C36 F36 118.1(14) . . ? C35 C36 C31 122.6(14) . . ? F36 C36 C31 119.3(11) . . ? C41 S4 Bi2 106.1(3) . . ? C41 S4 Bi1 105.6(4) . . ? Bi2 S4 Bi1 93.05(9) . . ? C42 C41 C46 114.7(10) . . ? C42 C41 S4 124.8(8) . . ? C46 C41 S4 120.4(9) . . ? F42 C42 C43 116.5(10) . . ? F42 C42 C41 118.9(10) . . ? C43 C42 C41 124.6(10) . . ? F43 C43 C42 121.7(10) . . ? F43 C43 C44 120.4(10) . . ? C42 C43 C44 117.9(11) . . ? F44 C44 C43 119.8(11) . . ? F44 C44 C45 119.8(11) . . ? C43 C44 C45 120.4(11) . . ? F45 C45 C46 120.6(11) . . ? F45 C45 C44 119.8(10) . . ? C46 C45 C44 119.6(11) . . ? F46 C46 C45 117.4(10) . . ? F46 C46 C41 119.8(10) . . ? C45 C46 C41 122.8(11) . . ? C51 S5 Bi2 99.3(4) . . ? C56 C51 C52 116.4(11) . . ? C56 C51 S5 122.9(9) . . ? C52 C51 S5 120.7(10) . . ? F52 C52 C53 119.1(13) . . ? F52 C52 C51 119.7(12) . . ? C53 C52 C51 121.2(14) . . ? C54 C53 F53 119.8(15) . . ? C54 C53 C52 121.5(14) . . ? F53 C53 C52 118.7(16) . . ? C53 C54 F54 122.8(16) . . ? C53 C54 C55 118.8(13) . . ? F54 C54 C55 118.4(15) . . ? F55 C55 C56 120.7(14) . . ? F55 C55 C54 120.0(13) . . ? C56 C55 C54 119.2(13) . . ? C51 C56 C55 122.8(13) . . ? C51 C56 F56 121.2(11) . . ? C55 C56 F56 116.0(12) . . ? C61 S6 Bi2 108.1(3) . . ? C62 C61 C66 116.8(10) . . ? C62 C61 S6 121.2(9) . . ? C66 C61 S6 121.6(9) . . ? F62 C62 C61 120.7(11) . . ? F62 C62 C63 118.3(12) . . ? C61 C62 C63 120.9(11) . . ? C64 C63 F63 118.5(12) . . ? C64 C63 C62 120.8(12) . . ? F63 C63 C62 120.7(13) . . ? F64 C64 C63 121.4(14) . . ? F64 C64 C65 118.9(14) . . ? C63 C64 C65 119.7(12) . . ? F65 C65 C66 118.5(13) . . ? F65 C65 C64 121.2(13) . . ? C66 C65 C64 120.3(12) . . ? F66 C66 C65 119.4(11) . . ? F66 C66 C61 119.2(11) . . ? C65 C66 C61 121.4(11) . . ? C71 S7 Bi2 100.2(4) . . ? C72 C71 C76 117.5(12) . . ? C72 C71 S7 122.6(9) . . ? C76 C71 S7 119.7(11) . . ? F72 C72 C71 120.7(12) . . ? F72 C72 C73 116.3(14) . . ? C71 C72 C73 122.9(13) . . ? C74 C73 F73 121.6(15) . . ? C74 C73 C72 118.8(16) . . ? F73 C73 C72 119.5(14) . . ? F74 C74 C73 121.5(17) . . ? F74 C74 C75 117.6(15) . . ? C73 C74 C75 120.9(15) . . ? F75 C75 C74 121.1(15) . . ? F75 C75 C76 119.3(15) . . ? C74 C75 C76 119.6(13) . . ? F76 C76 C71 121.5(13) . . ? F76 C76 C75 118.4(12) . . ? C71 C76 C75 120.1(14) . . ? C81 S8 Bi2 116.5(4) . . ? C81 S8 Bi3 108.5(4) . . ? Bi2 S8 Bi3 99.08(9) . . ? C82 C81 C86 116.7(10) . . ? C82 C81 S8 118.9(9) . . ? C86 C81 S8 124.4(8) . . ? F82 C82 C81 121.0(11) . . ? F82 C82 C83 117.4(11) . . ? C81 C82 C83 121.7(12) . . ? F83 C83 C82 120.0(12) . . ? F83 C83 C84 119.8(11) . . ? C82 C83 C84 120.2(12) . . ? F84 C84 C85 122.9(12) . . ? F84 C84 C83 119.4(11) . . ? C85 C84 C83 117.7(11) . . ? F85 C85 C86 121.1(11) . . ? F85 C85 C84 117.6(11) . . ? C86 C85 C84 121.3(11) . . ? C85 C86 F86 119.0(10) . . ? C85 C86 C81 122.5(11) . . ? F86 C86 C81 118.5(10) . . ? C91 S9 Bi3 99.2(4) . . ? C92 C91 C96 115.5(11) . . ? C92 C91 S9 123.1(9) . . ? C96 C91 S9 121.4(8) . . ? F92 C92 C91 120.7(11) . . ? F92 C92 C93 117.0(10) . . ? C91 C92 C93 122.3(11) . . ? F93 C93 C94 120.7(11) . . ? F93 C93 C92 119.3(11) . . ? C94 C93 C92 120.0(11) . . ? F94 C94 C93 119.2(11) . . ? F94 C94 C95 120.0(10) . . ? C93 C94 C95 120.6(11) . . ? F95 C95 C94 121.1(11) . . ? F95 C95 C96 120.6(11) . . ? C94 C95 C96 118.3(11) . . ? F96 C96 C95 116.6(10) . . ? F96 C96 C91 120.3(11) . . ? C95 C96 C91 123.1(11) . . ? C101 S10 Bi3 93.5(4) . . ? C102 C101 C106 118.8(13) . . ? C102 C101 S10 120.5(10) . . ? C106 C101 S10 120.7(11) . . ? F102 C102 C101 121.5(12) . . ? F102 C102 C103 116.7(15) . . ? C101 C102 C103 121.7(15) . . ? C104 C103 F103 120.2(16) . . ? C104 C103 C102 120.5(17) . . ? F103 C103 C102 119.4(16) . . ? F104 C104 C103 121.9(19) . . ? F104 C104 C105 119.3(16) . . ? C103 C104 C105 118.8(15) . . ? F105 C105 C106 121.4(17) . . ? F105 C105 C104 119.0(15) . . ? C106 C105 C104 119.5(15) . . ? F106 C106 C101 122.5(12) . . ? F106 C106 C105 116.7(14) . . ? C101 C106 C105 120.7(15) . . ? C111 S11 Bi3 101.6(4) . . ? C112 C111 C116 120.0 . . ? C112 C111 S11 115.4(10) . . ? C116 C111 S11 124.6(10) . . ? F112 C112 C111 127.2(12) . . ? F112 C112 C113 112.8(12) . . ? C111 C112 C113 120.0 . . ? F113 C113 C114 122.7(13) . . ? F113 C113 C112 116.9(13) . . ? C114 C113 C112 120.0 . . ? C113 C114 C115 120.0 . . ? C113 C114 F114 106.1(13) . . ? C115 C114 F114 133.7(13) . . ? F115 C115 C116 135.5(15) . . ? F115 C115 C114 104.5(15) . . ? C116 C115 C114 120.0 . . ? F116 C116 C115 118.6(15) . . ? F116 C116 C111 121.0(14) . . ? C115 C116 C111 120.0 . . ? N911 C916 C915 119.1(14) . . ? C914 N911 C916 121.9(13) . . ? C913 C912 C915 118.9(13) . . ? C913 C912 C911 122.0(16) . . ? C915 C912 C911 119.1(15) . . ? N911 C914 C913 119.8(14) . . ? C912 C915 C916 119.7(14) . . ? C912 C913 C914 120.5(15) . . ? C926 N921 C924 115.3(15) . . ? C904 N901 C906 117.5(14) . . ? C925 C922 C923 116.6(15) . . ? C925 C922 C921 122.5(16) . . ? C923 C922 C921 120.7(16) . . ? N901 C906 C905 124.1(15) . . ? N901 C904 C903 123.0(13) . . ? N921 C924 C923 125.4(16) . . ? C924 C923 C922 118.2(15) . . ? C922 C925 C926 120.9(16) . . ? C904 C903 C902 119.8(15) . . ? C902 C905 C906 119.4(16) . . ? N921 C926 C925 123.4(16) . . ? C905 C902 C903 116.2(16) . . ? C905 C902 C901 121.7(17) . . ? C903 C902 C901 122.1(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.281 _refine_diff_density_min -1.168 _refine_diff_density_rms 0.160 #===END data_13 _database_code_CSD 211644 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C24 H12 Bi F10 N S2), C5 H10' _chemical_formula_sum 'C53 H34 Bi2 F20 N2 S4' _chemical_formula_weight 1625.02 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.7168(18) _cell_length_b 13.9845(19) _cell_length_c 16.666(2) _cell_angle_alpha 69.780(2) _cell_angle_beta 81.689(2) _cell_angle_gamma 65.438(2) _cell_volume 2728.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 249 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description yellow _exptl_crystal_colour block _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.978 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 6.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.326 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD Area Detector' _diffrn_measurement_method '/w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8065 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.52 _reflns_number_total 8065 _reflns_number_gt 5482 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0422P)^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 8065 _refine_ls_number_parameters 733 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.960 _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 0.25342(3) 0.25923(3) 0.26455(2) 0.02588(11) Uani 1 1 d . . . Bi2 Bi 0.22216(3) 0.58356(4) 0.24674(2) 0.02633(11) Uani 1 1 d . . . S1 S 0.4037(2) 0.3466(3) 0.27072(18) 0.0284(7) Uani 1 1 d . . . S2 S 0.4039(2) 0.0592(3) 0.28961(19) 0.0346(7) Uani 1 1 d . . . S3 S 0.0697(2) 0.7721(3) 0.2540(2) 0.0352(7) Uani 1 1 d . . . S4 S 0.0712(2) 0.4895(3) 0.26401(19) 0.0292(7) Uani 1 1 d . . . F1 F 0.6277(5) 0.3287(7) 0.2488(5) 0.050(2) Uani 1 1 d . . . F2 F 0.7492(6) 0.3346(8) 0.1068(6) 0.065(2) Uani 1 1 d . . . F3 F 0.6699(6) 0.3609(7) -0.0431(5) 0.058(2) Uani 1 1 d . . . F4 F 0.4643(6) 0.3828(6) -0.0493(4) 0.0479(19) Uani 1 1 d . . . F5 F 0.3411(5) 0.3780(6) 0.0906(4) 0.0416(17) Uani 1 1 d . . . F6 F 0.6229(5) 0.0602(6) 0.2572(4) 0.0462(18) Uani 1 1 d . . . F7 F 0.7323(6) 0.0817(8) 0.1094(5) 0.054(2) Uani 1 1 d . . . F8 F 0.6385(6) 0.1192(7) -0.0379(5) 0.061(2) Uani 1 1 d . . . F9 F 0.4361(6) 0.1315(7) -0.0338(5) 0.058(2) Uani 1 1 d . . . F10 F 0.3284(5) 0.1038(6) 0.1140(5) 0.0474(18) Uani 1 1 d . . . F11 F -0.1500(5) 0.7990(6) 0.2174(4) 0.0479(19) Uani 1 1 d . . . F12 F -0.2427(6) 0.8654(7) 0.0687(5) 0.054(2) Uani 1 1 d . . . F13 F -0.1337(7) 0.9168(8) -0.0792(5) 0.060(2) Uani 1 1 d . . . F14 F 0.0690(6) 0.9000(7) -0.0743(5) 0.059(2) Uani 1 1 d . . . F15 F 0.1628(6) 0.8359(7) 0.0770(5) 0.047(2) Uani 1 1 d . . . F16 F 0.1522(6) 0.5690(6) 0.0810(4) 0.0412(18) Uani 1 1 d . . . F17 F 0.0417(6) 0.6541(6) -0.0648(4) 0.0480(18) Uani 1 1 d . . . F18 F -0.1611(7) 0.6706(7) -0.0624(5) 0.055(2) Uani 1 1 d . . . F19 F -0.2588(6) 0.6073(8) 0.0901(6) 0.067(3) Uani 1 1 d . . . F20 F -0.1505(5) 0.5235(6) 0.2352(4) 0.0465(19) Uani 1 1 d . . . N1 N 0.1102(8) 0.1812(9) 0.2769(7) 0.040(3) Uani 1 1 d . . . N2 N 0.3633(8) 0.6570(9) 0.2555(6) 0.033(2) Uani 1 1 d . . . C1 C 0.2468(8) 0.2208(9) 0.4066(7) 0.029(2) Uani 1 1 d . . . C2 C 0.1478(11) 0.2470(12) 0.4498(8) 0.048(4) Uani 1 1 d . . . H2A H 0.0826 0.2844 0.4185 0.058 Uiso 1 1 calc R . . C3 C 0.1461(11) 0.2186(11) 0.5364(8) 0.048(3) Uani 1 1 d . . . H3A H 0.0789 0.2372 0.5649 0.057 Uiso 1 1 calc R . . C4 C 0.2396(12) 0.1629(11) 0.5849(8) 0.053(4) Uani 1 1 d . . . H4A H 0.2364 0.1405 0.6456 0.064 Uiso 1 1 calc R . . C5 C 0.3395(11) 0.1404(11) 0.5422(8) 0.048(3) Uani 1 1 d . . . H5A H 0.4044 0.1075 0.5735 0.058 Uiso 1 1 calc R . . C6 C 0.3416(9) 0.1673(11) 0.4532(7) 0.041(3) Uani 1 1 d . . . H6A H 0.4084 0.1488 0.4242 0.049 Uiso 1 1 calc R . . C7 C 0.4783(8) 0.3535(9) 0.1754(7) 0.029(2) Uani 1 1 d . . . C8 C 0.5841(9) 0.3418(10) 0.1762(8) 0.038(3) Uani 1 1 d . . . C9 C 0.6472(8) 0.3462(10) 0.1033(8) 0.040(3) Uani 1 1 d . . . C10 C 0.6087(10) 0.3564(11) 0.0299(9) 0.042(3) Uani 1 1 d . . . C11 C 0.5059(9) 0.3674(10) 0.0259(8) 0.033(3) Uani 1 1 d . . . C12 C 0.4414(8) 0.3691(9) 0.0974(7) 0.030(2) Uani 1 1 d . . . C13 C 0.4694(8) 0.0830(9) 0.1909(7) 0.030(3) Uani 1 1 d . . . C14 C 0.5763(8) 0.0774(9) 0.1844(8) 0.032(3) Uani 1 1 d . . . C15 C 0.6322(8) 0.0903(9) 0.1109(7) 0.034(3) Uani 1 1 d . . . C16 C 0.5861(10) 0.1064(11) 0.0371(8) 0.041(3) Uani 1 1 d . . . C17 C 0.4824(11) 0.1144(11) 0.0391(8) 0.045(3) Uani 1 1 d . . . C18 C 0.4267(8) 0.0986(9) 0.1154(7) 0.034(3) Uani 1 1 d . . . C19 C 0.0057(11) 0.2473(12) 0.2778(9) 0.052(4) Uani 1 1 d . . . H19A H -0.0139 0.3202 0.2794 0.062 Uiso 1 1 calc R . . C20 C -0.0738(10) 0.2115(12) 0.2765(9) 0.053(4) Uani 1 1 d . . . H20A H -0.1468 0.2613 0.2743 0.063 Uiso 1 1 calc R . . C21 C -0.0492(11) 0.1067(11) 0.2784(8) 0.039(3) Uani 1 1 d . . . C22 C 0.0547(11) 0.0426(13) 0.2757(10) 0.054(4) Uani 1 1 d . . . H22A H 0.0753 -0.0312 0.2758 0.065 Uiso 1 1 calc R . . C23 C 0.1346(11) 0.0832(12) 0.2729(9) 0.052(4) Uani 1 1 d . . . H23A H 0.2078 0.0373 0.2680 0.062 Uiso 1 1 calc R . . C24 C -0.1360(10) 0.0678(12) 0.2770(9) 0.052(4) Uani 1 1 d . . . H24A H -0.1038 -0.0047 0.2678 0.078 Uiso 1 1 calc R . . H24B H -0.1863 0.1214 0.2306 0.078 Uiso 1 1 calc R . . H24C H -0.1744 0.0614 0.3317 0.078 Uiso 1 1 calc R . . C25 C 0.2202(10) 0.5255(10) 0.3900(7) 0.036(3) Uani 1 1 d . . . C26 C 0.1235(9) 0.5491(10) 0.4339(7) 0.038(3) Uani 1 1 d . . . H26A H 0.0582 0.5912 0.4029 0.046 Uiso 1 1 calc R . . C27 C 0.1211(12) 0.5128(12) 0.5208(8) 0.053(4) Uani 1 1 d . . . H27A H 0.0540 0.5293 0.5496 0.064 Uiso 1 1 calc R . . C28 C 0.2126(13) 0.4536(14) 0.5669(9) 0.067(5) Uani 1 1 d . . . H28A H 0.2093 0.4289 0.6275 0.081 Uiso 1 1 calc R . . C29 C 0.3129(13) 0.4283(14) 0.5257(9) 0.064(5) Uani 1 1 d . . . H29A H 0.3776 0.3892 0.5577 0.077 Uiso 1 1 calc R . . C30 C 0.3148(10) 0.4620(12) 0.4368(9) 0.052(4) Uani 1 1 d . . . H30A H 0.3815 0.4414 0.4078 0.062 Uiso 1 1 calc R . . C32 C -0.0925(9) 0.8246(9) 0.1477(7) 0.033(3) Uani 1 1 d . . . C33 C -0.1415(9) 0.8576(10) 0.0710(8) 0.037(3) Uani 1 1 d . . . C34 C -0.0873(10) 0.8841(10) -0.0032(8) 0.044(3) Uani 1 1 d . . . C31 C 0.0116(8) 0.8138(9) 0.1549(7) 0.030(2) Uani 1 1 d . . . C35 C 0.0166(10) 0.8752(12) -0.0015(8) 0.040(3) Uani 1 1 d . . . C36 C 0.0621(8) 0.8431(9) 0.0771(7) 0.030(3) Uani 1 1 d . . . C37 C 0.0065(8) 0.5413(9) 0.1656(6) 0.027(2) Uani 1 1 d . . . C38 C 0.0498(8) 0.5773(9) 0.0852(6) 0.026(2) Uani 1 1 d . . . C39 C -0.0050(10) 0.6192(11) 0.0119(8) 0.036(3) Uani 1 1 d . . . C40 C -0.1083(9) 0.6300(10) 0.0112(8) 0.036(3) Uani 1 1 d . . . C41 C -0.1557(9) 0.5974(10) 0.0873(8) 0.039(3) Uani 1 1 d . . . C42 C -0.1003(8) 0.5549(9) 0.1622(7) 0.032(3) Uani 1 1 d . . . C43 C 0.4653(11) 0.5897(12) 0.2598(10) 0.056(4) Uani 1 1 d . . . H43A H 0.4834 0.5153 0.2625 0.068 Uiso 1 1 calc R . . C44 C 0.5473(10) 0.6228(12) 0.2604(10) 0.055(4) Uani 1 1 d . . . H44A H 0.6194 0.5704 0.2689 0.066 Uiso 1 1 calc R . . C45 C 0.5221(9) 0.7340(9) 0.2482(7) 0.029(3) Uani 1 1 d . . . C46 C 0.4173(10) 0.7999(12) 0.2412(9) 0.049(4) Uani 1 1 d . . . H46A H 0.3961 0.8763 0.2338 0.058 Uiso 1 1 calc R . . C47 C 0.3401(10) 0.7610(12) 0.2444(9) 0.055(4) Uani 1 1 d . . . H47A H 0.2671 0.8114 0.2383 0.066 Uiso 1 1 calc R . . C48 C 0.6078(9) 0.7785(10) 0.2463(9) 0.041(3) Uani 1 1 d . . . H48A H 0.5948 0.8097 0.2932 0.062 Uiso 1 1 calc R . . H48B H 0.6044 0.8364 0.1916 0.062 Uiso 1 1 calc R . . H48C H 0.6789 0.7179 0.2531 0.062 Uiso 1 1 calc R . . C1S C 0.398(3) -0.233(3) 0.503(3) 0.33(2) Uani 1 1 d DU . . H1S1 H 0.4568 -0.2693 0.5458 0.394 Uiso 1 1 calc R . . H1S2 H 0.4302 -0.2204 0.4452 0.394 Uiso 1 1 calc R . . C2S C 0.313(4) -0.119(3) 0.515(2) 0.31(2) Uani 1 1 d DU . . H2S1 H 0.3319 -0.0564 0.4789 0.367 Uiso 1 1 calc R . . H2S2 H 0.3104 -0.1220 0.5757 0.367 Uiso 1 1 calc R . . C3S C 0.200(3) -0.107(3) 0.486(3) 0.34(2) Uani 1 1 d DU . . H3S1 H 0.1448 -0.0904 0.5304 0.406 Uiso 1 1 calc R . . H3S2 H 0.1761 -0.0460 0.4319 0.406 Uiso 1 1 calc R . . C4S C 0.216(3) -0.221(4) 0.474(3) 0.34(2) Uani 1 1 d DU . . H4S1 H 0.2150 -0.2130 0.4129 0.410 Uiso 1 1 calc R . . H4S2 H 0.1578 -0.2454 0.5037 0.410 Uiso 1 1 calc R . . C5S C 0.332(4) -0.310(2) 0.517(3) 0.32(2) Uani 1 1 d DU . . H5S1 H 0.3246 -0.3473 0.5786 0.386 Uiso 1 1 calc R . . H5S2 H 0.3672 -0.3664 0.4878 0.386 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0257(2) 0.0310(3) 0.0227(2) -0.0076(2) 0.00136(18) -0.0140(2) Bi2 0.0257(2) 0.0301(3) 0.0251(2) -0.00850(19) 0.00110(18) -0.0134(2) S1 0.0238(14) 0.0334(17) 0.0299(16) -0.0109(13) 0.0019(12) -0.0131(13) S2 0.0327(16) 0.0285(17) 0.0365(17) -0.0091(13) 0.0032(13) -0.0084(13) S3 0.0351(17) 0.0322(18) 0.0380(18) -0.0135(14) -0.0031(13) -0.0102(14) S4 0.0273(15) 0.0348(18) 0.0265(15) -0.0089(13) 0.0015(12) -0.0146(14) F1 0.031(4) 0.068(6) 0.054(5) -0.023(4) -0.004(3) -0.017(4) F2 0.038(5) 0.083(7) 0.079(6) -0.024(5) 0.017(4) -0.035(5) F3 0.055(5) 0.060(6) 0.052(5) -0.018(4) 0.028(4) -0.025(4) F4 0.057(5) 0.061(5) 0.025(4) -0.008(3) 0.004(3) -0.029(4) F5 0.032(4) 0.061(5) 0.031(4) -0.006(3) -0.003(3) -0.023(4) F6 0.040(4) 0.059(5) 0.038(4) -0.010(4) -0.012(3) -0.018(4) F7 0.033(4) 0.073(6) 0.056(5) -0.022(4) 0.005(4) -0.023(4) F8 0.050(5) 0.088(7) 0.051(5) -0.027(5) 0.019(4) -0.035(5) F9 0.058(5) 0.087(7) 0.036(5) -0.024(4) -0.004(4) -0.031(5) F10 0.029(4) 0.062(5) 0.059(5) -0.020(4) -0.001(3) -0.025(4) F11 0.037(4) 0.063(5) 0.046(4) -0.016(4) 0.009(3) -0.026(4) F12 0.028(4) 0.064(6) 0.073(6) -0.028(5) -0.006(4) -0.014(4) F13 0.053(5) 0.090(7) 0.038(5) -0.013(5) -0.003(4) -0.032(5) F14 0.056(5) 0.076(6) 0.044(5) -0.012(4) 0.011(4) -0.036(5) F15 0.033(4) 0.059(5) 0.052(5) -0.012(4) 0.006(3) -0.027(4) F16 0.028(4) 0.066(6) 0.030(4) -0.018(4) 0.000(3) -0.017(4) F17 0.059(5) 0.057(5) 0.024(4) -0.009(3) 0.002(3) -0.022(4) F18 0.056(5) 0.060(6) 0.045(5) -0.008(4) -0.026(4) -0.016(4) F19 0.027(4) 0.104(8) 0.070(6) -0.021(5) -0.008(4) -0.028(5) F20 0.031(4) 0.072(6) 0.048(4) -0.024(4) 0.012(3) -0.031(4) N1 0.039(6) 0.042(7) 0.041(6) -0.007(5) -0.005(5) -0.022(6) N2 0.037(6) 0.038(6) 0.037(6) -0.013(5) 0.001(4) -0.026(5) C1 0.027(6) 0.036(7) 0.029(6) -0.011(5) 0.001(5) -0.015(5) C2 0.046(8) 0.055(9) 0.035(7) -0.003(6) 0.013(6) -0.025(7) C3 0.053(8) 0.053(9) 0.041(8) -0.028(7) 0.016(6) -0.018(7) C4 0.072(10) 0.056(10) 0.021(6) -0.002(6) 0.002(6) -0.024(8) C5 0.054(8) 0.046(9) 0.040(8) -0.013(7) -0.007(6) -0.013(7) C6 0.031(6) 0.054(9) 0.030(7) -0.004(6) -0.002(5) -0.016(6) C7 0.021(5) 0.032(7) 0.032(6) -0.009(5) -0.002(4) -0.009(5) C8 0.027(6) 0.039(8) 0.042(7) -0.007(6) 0.001(5) -0.013(5) C9 0.011(5) 0.045(8) 0.059(8) -0.011(6) 0.006(5) -0.014(5) C10 0.039(8) 0.038(8) 0.046(8) -0.020(6) 0.012(6) -0.011(6) C11 0.040(7) 0.030(7) 0.034(7) -0.013(5) 0.001(5) -0.015(5) C12 0.029(6) 0.031(7) 0.032(6) -0.006(5) 0.001(5) -0.018(5) C13 0.020(6) 0.026(6) 0.039(7) -0.012(5) 0.003(5) -0.005(5) C14 0.023(6) 0.017(6) 0.048(8) -0.006(5) -0.002(5) -0.003(5) C15 0.017(6) 0.030(7) 0.041(7) -0.005(5) 0.000(5) 0.001(5) C16 0.033(7) 0.050(9) 0.037(7) -0.016(6) 0.011(6) -0.015(6) C17 0.064(9) 0.051(9) 0.028(7) -0.018(6) -0.004(6) -0.027(7) C18 0.022(6) 0.034(7) 0.043(7) -0.015(6) 0.002(5) -0.008(5) C19 0.056(9) 0.036(9) 0.062(10) -0.006(7) 0.006(7) -0.026(7) C20 0.030(7) 0.046(9) 0.071(10) 0.003(7) -0.011(6) -0.020(7) C21 0.051(8) 0.042(8) 0.033(7) -0.006(6) -0.001(6) -0.032(7) C22 0.038(8) 0.043(10) 0.083(12) -0.019(8) 0.002(8) -0.017(7) C23 0.044(8) 0.051(10) 0.074(10) -0.019(8) -0.008(7) -0.031(8) C24 0.048(8) 0.069(11) 0.062(9) -0.021(8) 0.000(7) -0.044(8) C25 0.043(7) 0.037(7) 0.025(6) 0.000(5) -0.003(5) -0.019(6) C26 0.034(7) 0.040(8) 0.033(7) -0.010(6) 0.007(5) -0.011(6) C27 0.056(9) 0.060(10) 0.028(7) -0.007(7) 0.015(6) -0.019(8) C28 0.083(12) 0.071(12) 0.032(8) -0.023(8) 0.018(8) -0.016(9) C29 0.076(11) 0.086(13) 0.023(7) -0.015(8) -0.007(7) -0.024(9) C30 0.036(7) 0.060(10) 0.050(8) -0.025(7) -0.010(6) 0.000(7) C32 0.035(6) 0.018(6) 0.032(6) -0.004(5) 0.007(5) -0.002(5) C33 0.032(7) 0.035(7) 0.045(8) -0.015(6) -0.002(5) -0.012(6) C34 0.040(7) 0.035(8) 0.038(7) -0.003(6) -0.017(6) 0.003(6) C31 0.021(5) 0.021(6) 0.043(7) -0.003(5) -0.001(5) -0.009(5) C35 0.036(7) 0.041(8) 0.042(8) -0.012(6) 0.007(6) -0.019(6) C36 0.016(5) 0.024(6) 0.043(7) -0.009(5) 0.006(5) -0.005(5) C37 0.026(6) 0.024(6) 0.026(6) -0.006(5) -0.003(4) -0.007(5) C38 0.032(6) 0.028(6) 0.022(5) -0.008(5) 0.002(4) -0.015(5) C39 0.040(8) 0.046(8) 0.026(6) -0.017(5) 0.001(5) -0.016(6) C40 0.032(7) 0.037(7) 0.039(7) -0.016(6) -0.014(5) -0.004(6) C41 0.028(6) 0.043(8) 0.046(8) -0.016(6) -0.016(5) -0.007(6) C42 0.025(6) 0.036(7) 0.036(6) -0.012(5) 0.002(5) -0.013(5) C43 0.046(8) 0.034(9) 0.094(12) -0.020(8) 0.004(8) -0.021(7) C44 0.027(7) 0.054(10) 0.083(11) -0.027(8) -0.005(7) -0.010(7) C45 0.029(6) 0.026(7) 0.028(6) 0.000(5) -0.002(5) -0.015(5) C46 0.039(8) 0.044(9) 0.069(10) -0.012(7) -0.003(7) -0.026(7) C47 0.029(7) 0.037(8) 0.089(11) -0.011(8) -0.008(7) -0.008(6) C48 0.035(7) 0.025(7) 0.055(8) -0.007(6) -0.005(6) -0.007(6) C1S 0.58(5) 0.16(3) 0.19(3) -0.06(2) 0.00(3) -0.09(3) C2S 0.62(6) 0.15(2) 0.08(2) -0.047(19) 0.03(3) -0.10(3) C3S 0.61(5) 0.17(2) 0.14(3) -0.02(2) -0.01(3) -0.07(3) C4S 0.60(6) 0.17(3) 0.18(3) -0.02(3) -0.05(3) -0.09(3) C5S 0.59(6) 0.16(2) 0.17(3) -0.05(3) -0.06(3) -0.09(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.237(10) . ? Bi1 N1 2.569(10) . ? Bi1 S2 2.627(3) . ? Bi1 S1 2.827(3) . ? Bi2 C25 2.240(11) . ? Bi2 N2 2.582(9) . ? Bi2 S3 2.627(3) . ? Bi2 S4 2.817(3) . ? S1 C7 1.757(10) . ? S2 C13 1.751(11) . ? S3 C31 1.741(12) . ? S4 C37 1.750(11) . ? F1 C8 1.349(13) . ? F2 C9 1.347(12) . ? F3 C10 1.373(13) . ? F4 C11 1.365(13) . ? F5 C12 1.346(11) . ? F6 C14 1.354(13) . ? F7 C15 1.324(12) . ? F8 C16 1.342(13) . ? F9 C17 1.355(14) . ? F10 C18 1.322(12) . ? F11 C32 1.336(11) . ? F12 C33 1.351(13) . ? F13 C34 1.345(14) . ? F14 C35 1.332(13) . ? F15 C36 1.342(12) . ? F16 C38 1.353(12) . ? F17 C39 1.368(13) . ? F18 C40 1.335(13) . ? F19 C41 1.358(13) . ? F20 C42 1.336(12) . ? N1 C23 1.292(16) . ? N1 C19 1.346(16) . ? N2 C47 1.302(16) . ? N2 C43 1.318(16) . ? C1 C6 1.391(15) . ? C1 C2 1.408(15) . ? C2 C3 1.358(17) . ? C3 C4 1.393(18) . ? C4 C5 1.414(18) . ? C5 C6 1.398(17) . ? C7 C12 1.378(15) . ? C7 C8 1.392(14) . ? C8 C9 1.385(15) . ? C9 C10 1.342(18) . ? C10 C11 1.362(17) . ? C11 C12 1.378(14) . ? C13 C18 1.376(15) . ? C13 C14 1.426(14) . ? C14 C15 1.345(14) . ? C15 C16 1.371(17) . ? C16 C17 1.376(17) . ? C17 C18 1.383(16) . ? C19 C20 1.381(17) . ? C20 C21 1.350(18) . ? C21 C22 1.335(18) . ? C21 C24 1.507(16) . ? C22 C23 1.419(18) . ? C25 C26 1.388(15) . ? C25 C30 1.393(16) . ? C26 C27 1.359(16) . ? C27 C28 1.35(2) . ? C28 C29 1.41(2) . ? C29 C30 1.390(18) . ? C32 C33 1.372(16) . ? C32 C31 1.391(14) . ? C33 C34 1.365(16) . ? C34 C35 1.383(16) . ? C31 C36 1.391(14) . ? C35 C36 1.379(17) . ? C37 C38 1.398(13) . ? C37 C42 1.405(14) . ? C38 C39 1.345(16) . ? C39 C40 1.363(16) . ? C40 C41 1.360(16) . ? C41 C42 1.369(15) . ? C43 C44 1.384(17) . ? C44 C45 1.392(17) . ? C45 C46 1.343(16) . ? C45 C48 1.534(16) . ? C46 C47 1.365(18) . ? C1S C2S 1.60(2) . ? C1S C5S 1.61(2) . ? C2S C3S 1.62(2) . ? C3S C4S 1.596(19) . ? C4S C5S 1.63(2) . ? 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 N1 88.7(4) . . ? C1 Bi1 S2 87.2(3) . . ? N1 Bi1 S2 89.8(3) . . ? C1 Bi1 S1 84.8(3) . . ? N1 Bi1 S1 173.2(2) . . ? S2 Bi1 S1 91.85(9) . . ? C25 Bi2 N2 87.3(4) . . ? C25 Bi2 S3 87.1(3) . . ? N2 Bi2 S3 89.4(2) . . ? C25 Bi2 S4 84.1(3) . . ? N2 Bi2 S4 171.4(2) . . ? S3 Bi2 S4 91.11(9) . . ? C7 S1 Bi1 108.1(4) . . ? C13 S2 Bi1 98.5(4) . . ? C31 S3 Bi2 97.9(4) . . ? C37 S4 Bi2 108.2(4) . . ? C23 N1 C19 118.0(12) . . ? C23 N1 Bi1 121.8(9) . . ? C19 N1 Bi1 119.8(9) . . ? C47 N2 C43 117.9(11) . . ? C47 N2 Bi2 123.0(8) . . ? C43 N2 Bi2 118.4(9) . . ? C6 C1 C2 119.6(11) . . ? C6 C1 Bi1 119.6(8) . . ? C2 C1 Bi1 120.8(9) . . ? C3 C2 C1 119.6(13) . . ? C2 C3 C4 122.2(12) . . ? C3 C4 C5 118.8(12) . . ? C6 C5 C4 119.0(13) . . ? C1 C6 C5 120.7(11) . . ? C12 C7 C8 115.3(10) . . ? C12 C7 S1 125.4(8) . . ? C8 C7 S1 119.3(8) . . ? F1 C8 C9 117.5(10) . . ? F1 C8 C7 120.4(10) . . ? C9 C8 C7 122.1(11) . . ? C10 C9 F2 119.7(11) . . ? C10 C9 C8 120.0(10) . . ? F2 C9 C8 120.2(12) . . ? C9 C10 C11 120.1(11) . . ? C9 C10 F3 120.9(11) . . ? C11 C10 F3 118.9(12) . . ? C10 C11 F4 120.7(11) . . ? C10 C11 C12 119.7(11) . . ? F4 C11 C12 119.5(10) . . ? F5 C12 C7 119.8(9) . . ? F5 C12 C11 117.4(10) . . ? C7 C12 C11 122.6(10) . . ? C18 C13 C14 114.6(10) . . ? C18 C13 S2 123.3(8) . . ? C14 C13 S2 121.8(9) . . ? C15 C14 F6 118.5(10) . . ? C15 C14 C13 124.4(11) . . ? F6 C14 C13 117.1(10) . . ? F7 C15 C14 121.4(11) . . ? F7 C15 C16 119.6(10) . . ? C14 C15 C16 118.9(10) . . ? F8 C16 C15 121.3(11) . . ? F8 C16 C17 119.3(12) . . ? C15 C16 C17 119.3(11) . . ? F9 C17 C16 119.6(11) . . ? F9 C17 C18 119.3(11) . . ? C16 C17 C18 121.1(11) . . ? F10 C18 C13 120.0(10) . . ? F10 C18 C17 118.5(11) . . ? C13 C18 C17 121.5(10) . . ? N1 C19 C20 121.6(14) . . ? C21 C20 C19 120.9(13) . . ? C22 C21 C20 117.0(13) . . ? C22 C21 C24 122.1(13) . . ? C20 C21 C24 120.8(12) . . ? C21 C22 C23 120.9(14) . . ? N1 C23 C22 121.5(13) . . ? C26 C25 C30 118.5(11) . . ? C26 C25 Bi2 120.3(9) . . ? C30 C25 Bi2 121.2(9) . . ? C27 C26 C25 120.9(12) . . ? C28 C27 C26 121.0(12) . . ? C27 C28 C29 120.5(13) . . ? C30 C29 C28 118.2(14) . . ? C29 C30 C25 120.7(13) . . ? F11 C32 C33 115.7(10) . . ? F11 C32 C31 120.6(10) . . ? C33 C32 C31 123.7(10) . . ? F12 C33 C34 120.4(11) . . ? F12 C33 C32 120.5(10) . . ? C34 C33 C32 119.1(11) . . ? F13 C34 C33 120.3(11) . . ? F13 C34 C35 119.0(11) . . ? C33 C34 C35 120.8(11) . . ? C32 C31 C36 114.4(10) . . ? C32 C31 S3 121.7(8) . . ? C36 C31 S3 123.9(8) . . ? F14 C35 C36 121.9(11) . . ? F14 C35 C34 120.1(11) . . ? C36 C35 C34 118.0(11) . . ? F15 C36 C35 116.8(10) . . ? F15 C36 C31 119.2(10) . . ? C35 C36 C31 123.9(10) . . ? C38 C37 C42 113.3(9) . . ? C38 C37 S4 126.0(8) . . ? C42 C37 S4 120.6(8) . . ? C39 C38 F16 118.4(9) . . ? C39 C38 C37 123.2(10) . . ? F16 C38 C37 118.4(9) . . ? C38 C39 C40 121.7(11) . . ? C38 C39 F17 120.4(11) . . ? C40 C39 F17 118.0(11) . . ? F18 C40 C41 121.0(11) . . ? F18 C40 C39 120.8(12) . . ? C41 C40 C39 118.2(11) . . ? F19 C41 C40 120.4(10) . . ? F19 C41 C42 119.1(11) . . ? C40 C41 C42 120.4(10) . . ? F20 C42 C41 118.0(10) . . ? F20 C42 C37 118.8(9) . . ? C41 C42 C37 123.2(10) . . ? N2 C43 C44 122.8(13) . . ? C43 C44 C45 118.9(12) . . ? C46 C45 C44 115.7(12) . . ? C46 C45 C48 121.7(11) . . ? C44 C45 C48 122.5(10) . . ? C45 C46 C47 122.4(14) . . ? N2 C47 C46 122.1(12) . . ? C2S C1S C5S 105.5(15) . . ? C1S C2S C3S 104.7(13) . . ? C4S C3S C2S 108.7(12) . . ? C3S C4S C5S 104.9(13) . . ? C1S C5S C4S 103.4(15) . . ? _diffrn_measured_fraction_theta_max 0.642 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.642 _refine_diff_density_max 1.086 _refine_diff_density_min -0.787 _refine_diff_density_rms 0.152 #===END # End of cif file