# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_cd201215 _database_code_depnum_ccdc_archive 'CCDC 773956' #TrackingRef 'cd201215.cif' _audit_update_record ; 2013-02-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;14-chloro-7,14-dihydro-5H-benzo(c)naphtho(1,2- f)(1,5)oxastibocine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Cl O Sb' _chemical_formula_weight 403.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7504(10) _cell_length_b 14.4272(12) _cell_length_c 8.9688(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.251(2) _cell_angle_gamma 90.00 _cell_volume 1518.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 5.354 _cell_measurement_theta_max 56.175 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.988 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6259 _exptl_absorpt_correction_T_max 0.8109 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8803 _diffrn_reflns_av_R_equivalents 0.1210 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3307 _reflns_number_gt 2903 _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^)+(0.0479P)^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 0.0179(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3307 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Sb Sb 0.305210(19) 0.567000(15) 0.91563(3) 0.03528(14) Uani 1 1 d . . . Cl1 Cl 0.28650(9) 0.46997(8) 0.68740(12) 0.0526(3) Uani 1 1 d . . . O1 O 0.3679(2) 0.69614(17) 1.0728(3) 0.0390(6) Uani 1 1 d . . . C1 C 0.4784(3) 0.6007(2) 0.8606(4) 0.0336(7) Uani 1 1 d . . . C2 C 0.5320(4) 0.5745(2) 0.7333(5) 0.0393(9) Uani 1 1 d . . . H2 H 0.4923 0.5404 0.6594 0.047 Uiso 1 1 calc R . . C3 C 0.6441(3) 0.5989(3) 0.7158(4) 0.0444(9) Uani 1 1 d . . . H3 H 0.6790 0.5809 0.6298 0.053 Uiso 1 1 calc R . . C4 C 0.7046(3) 0.6489(3) 0.8223(5) 0.0482(10) Uani 1 1 d . . . H4 H 0.7797 0.6658 0.8083 0.058 Uiso 1 1 calc R . . C5 C 0.6536(3) 0.6742(3) 0.9511(5) 0.0438(9) Uani 1 1 d . . . H5 H 0.6946 0.7080 1.0242 0.053 Uiso 1 1 calc R . . C6 C 0.5424(3) 0.6497(2) 0.9722(4) 0.0361(8) Uani 1 1 d . . . C7 C 0.4855(3) 0.6764(3) 1.1105(4) 0.0406(9) Uani 1 1 d . . . H7A H 0.4917 0.6263 1.1825 0.049 Uiso 1 1 calc R . . H7B H 0.5224 0.7307 1.1550 0.049 Uiso 1 1 calc R . . C8 C 0.3515(3) 0.7814(3) 0.9914(4) 0.0396(8) Uani 1 1 d . . . H8A H 0.4190 0.7954 0.9382 0.047 Uiso 1 1 calc R . . H8B H 0.3391 0.8318 1.0602 0.047 Uiso 1 1 calc R . . C9 C 0.2500(3) 0.7720(3) 0.8822(4) 0.0365(8) Uani 1 1 d . . . C10 C 0.1985(3) 0.8552(3) 0.8337(5) 0.0463(9) Uani 1 1 d . . . H10 H 0.2260 0.9114 0.8712 0.056 Uiso 1 1 calc R . . C11 C 0.1078(3) 0.8536(3) 0.7314(5) 0.0486(10) Uani 1 1 d . . . H11 H 0.0767 0.9090 0.6953 0.058 Uiso 1 1 calc R . . C12 C 0.0612(3) 0.7690(3) 0.6802(4) 0.0404(8) Uani 1 1 d . . . C13 C -0.0353(3) 0.7657(3) 0.5800(5) 0.0499(10) Uani 1 1 d . . . H13 H -0.0664 0.8209 0.5426 0.060 Uiso 1 1 calc R . . C14 C -0.0843(3) 0.6836(3) 0.5362(5) 0.0515(11) Uani 1 1 d . . . H14 H -0.1465 0.6828 0.4674 0.062 Uiso 1 1 calc R . . C15 C -0.0404(3) 0.6012(3) 0.5955(5) 0.0490(10) Uani 1 1 d . . . H15 H -0.0763 0.5455 0.5704 0.059 Uiso 1 1 calc R . . C16 C 0.0547(3) 0.6012(3) 0.6901(5) 0.0423(9) Uani 1 1 d . . . H16 H 0.0829 0.5450 0.7271 0.051 Uiso 1 1 calc R . . C17 C 0.1111(3) 0.6836(3) 0.7330(4) 0.0365(8) Uani 1 1 d . . . C18 C 0.2123(3) 0.6872(2) 0.8304(4) 0.0342(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 Sb 0.0435(2) 0.02541(18) 0.0371(2) 0.00041(9) 0.00387(12) -0.00378(8) Cl1 0.0564(6) 0.0432(6) 0.0570(6) -0.0197(5) -0.0085(5) 0.0023(4) O1 0.0451(14) 0.0352(14) 0.0373(13) -0.0035(11) 0.0080(11) -0.0028(11) C1 0.0424(18) 0.0245(16) 0.0337(17) 0.0019(15) 0.0022(14) 0.0056(14) C2 0.052(2) 0.0304(19) 0.036(2) 0.0000(15) 0.0015(17) 0.0086(15) C3 0.055(2) 0.038(2) 0.042(2) 0.0047(19) 0.0153(17) 0.0073(18) C4 0.042(2) 0.045(2) 0.059(3) 0.004(2) 0.0114(18) 0.0015(17) C5 0.045(2) 0.037(2) 0.049(2) -0.0036(18) 0.0009(17) -0.0027(16) C6 0.047(2) 0.0246(17) 0.0363(18) 0.0009(15) 0.0007(15) 0.0003(14) C7 0.045(2) 0.041(2) 0.0358(19) -0.0072(17) 0.0015(16) -0.0054(16) C8 0.046(2) 0.0302(19) 0.044(2) -0.0068(17) 0.0088(16) -0.0019(15) C9 0.0401(18) 0.0300(19) 0.0402(19) -0.0049(16) 0.0095(15) -0.0031(15) C10 0.050(2) 0.0259(19) 0.064(3) -0.0086(19) 0.0123(19) 0.0027(16) C11 0.051(2) 0.033(2) 0.062(3) 0.000(2) 0.0068(19) 0.0052(17) C12 0.0418(19) 0.034(2) 0.046(2) -0.0029(17) 0.0099(16) 0.0058(15) C13 0.048(2) 0.041(2) 0.061(3) 0.002(2) 0.0047(19) 0.0133(18) C14 0.038(2) 0.058(3) 0.058(3) -0.009(2) 0.0002(18) 0.0056(18) C15 0.039(2) 0.045(2) 0.063(3) -0.012(2) 0.0043(18) 0.0010(18) C16 0.0376(19) 0.0326(19) 0.057(2) -0.0035(19) 0.0066(16) -0.0003(16) C17 0.0369(18) 0.0315(19) 0.042(2) -0.0015(16) 0.0110(15) 0.0012(14) C18 0.0397(18) 0.0259(17) 0.0379(19) -0.0005(15) 0.0116(15) 0.0001(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb C18 2.165(3) . ? Sb C1 2.176(4) . ? Sb O1 2.425(2) . ? Sb Cl1 2.4793(10) . ? O1 C7 1.433(4) . ? O1 C8 1.437(4) . ? C1 C2 1.388(5) . ? C1 C6 1.407(5) . ? C2 C3 1.380(6) . ? C2 H2 0.9300 . ? C3 C4 1.364(6) . ? C3 H3 0.9300 . ? C4 C5 1.381(6) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C5 H5 0.9300 . ? C6 C7 1.493(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.505(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C18 1.374(5) . ? C9 C10 1.402(5) . ? C10 C11 1.366(5) . ? C10 H10 0.9300 . ? C11 C12 1.405(5) . ? C11 H11 0.9300 . ? C12 C13 1.407(6) . ? C12 C17 1.433(5) . ? C13 C14 1.364(6) . ? C13 H13 0.9300 . ? C14 C15 1.389(6) . ? C14 H14 0.9300 . ? C15 C16 1.364(5) . ? C15 H15 0.9300 . ? C16 C17 1.404(5) . ? C16 H16 0.9300 . ? C17 C18 1.436(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 C18 Sb C1 101.55(13) . . ? C18 Sb O1 73.77(11) . . ? C1 Sb O1 72.74(11) . . ? C18 Sb Cl1 98.12(10) . . ? C1 Sb Cl1 88.81(10) . . ? O1 Sb Cl1 157.43(7) . . ? C7 O1 C8 112.9(3) . . ? C7 O1 Sb 104.0(2) . . ? C8 O1 Sb 109.53(19) . . ? C2 C1 C6 118.2(3) . . ? C2 C1 Sb 126.9(3) . . ? C6 C1 Sb 114.9(2) . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.5(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 120.3(3) . . ? C5 C6 C7 121.4(3) . . ? C1 C6 C7 118.3(3) . . ? O1 C7 C6 109.1(3) . . ? O1 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O1 C8 C9 109.4(3) . . ? O1 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? O1 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C18 C9 C10 122.1(3) . . ? C18 C9 C8 121.9(3) . . ? C10 C9 C8 116.0(3) . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 121.5(4) . . ? C11 C12 C17 119.6(3) . . ? C13 C12 C17 118.8(3) . . ? C14 C13 C12 121.6(4) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.4(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 121.9(4) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C12 117.3(3) . . ? C16 C17 C18 124.0(3) . . ? C12 C17 C18 118.6(3) . . ? C9 C18 C17 118.5(3) . . ? C9 C18 Sb 116.6(2) . . ? C17 C18 Sb 124.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Sb O1 C7 -145.7(2) . . . . ? C1 Sb O1 C7 -37.7(2) . . . . ? Cl1 Sb O1 C7 -74.2(3) . . . . ? C18 Sb O1 C8 -24.8(2) . . . . ? C1 Sb O1 C8 83.2(2) . . . . ? Cl1 Sb O1 C8 46.7(3) . . . . ? C18 Sb C1 C2 -93.7(3) . . . . ? O1 Sb C1 C2 -162.5(3) . . . . ? Cl1 Sb C1 C2 4.3(3) . . . . ? C18 Sb C1 C6 90.2(3) . . . . ? O1 Sb C1 C6 21.5(2) . . . . ? Cl1 Sb C1 C6 -171.7(2) . . . . ? C6 C1 C2 C3 -2.1(5) . . . . ? Sb C1 C2 C3 -178.0(3) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C5 1.1(6) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C1 -1.8(6) . . . . ? C4 C5 C6 C7 -179.9(4) . . . . ? C2 C1 C6 C5 2.9(5) . . . . ? Sb C1 C6 C5 179.4(3) . . . . ? C2 C1 C6 C7 -178.9(3) . . . . ? Sb C1 C6 C7 -2.5(4) . . . . ? C8 O1 C7 C6 -71.6(4) . . . . ? Sb O1 C7 C6 47.0(3) . . . . ? C5 C6 C7 O1 144.5(3) . . . . ? C1 C6 C7 O1 -33.6(4) . . . . ? C7 O1 C8 C9 146.5(3) . . . . ? Sb O1 C8 C9 31.1(3) . . . . ? O1 C8 C9 C18 -23.5(5) . . . . ? O1 C8 C9 C10 158.1(3) . . . . ? C18 C9 C10 C11 -0.2(6) . . . . ? C8 C9 C10 C11 178.2(4) . . . . ? C9 C10 C11 C12 3.7(6) . . . . ? C10 C11 C12 C13 177.1(4) . . . . ? C10 C11 C12 C17 -1.6(6) . . . . ? C11 C12 C13 C14 -176.5(4) . . . . ? C17 C12 C13 C14 2.3(6) . . . . ? C12 C13 C14 C15 2.1(7) . . . . ? C13 C14 C15 C16 -3.7(7) . . . . ? C14 C15 C16 C17 0.9(7) . . . . ? C15 C16 C17 C12 3.4(6) . . . . ? C15 C16 C17 C18 -179.0(4) . . . . ? C11 C12 C17 C16 173.9(4) . . . . ? C13 C12 C17 C16 -4.9(6) . . . . ? C11 C12 C17 C18 -3.8(5) . . . . ? C13 C12 C17 C18 177.4(4) . . . . ? C10 C9 C18 C17 -5.3(6) . . . . ? C8 C9 C18 C17 176.5(3) . . . . ? C10 C9 C18 Sb 178.9(3) . . . . ? C8 C9 C18 Sb 0.6(5) . . . . ? C16 C17 C18 C9 -170.4(4) . . . . ? C12 C17 C18 C9 7.1(5) . . . . ? C16 C17 C18 Sb 5.1(5) . . . . ? C12 C17 C18 Sb -177.4(3) . . . . ? C1 Sb C18 C9 -55.2(3) . . . . ? O1 Sb C18 C9 12.8(3) . . . . ? Cl1 Sb C18 C9 -145.7(3) . . . . ? C1 Sb C18 C17 129.2(3) . . . . ? O1 Sb C18 C17 -162.8(3) . . . . ? Cl1 Sb C18 C17 38.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.314 _refine_diff_density_min -1.085 _refine_diff_density_rms 0.146 data_dm11266 _database_code_depnum_ccdc_archive 'CCDC 827987' #TrackingRef 'dm11266.cif' _audit_update_record ; 2011-06-01 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Bi Cl O' _chemical_formula_weight 490.72 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 20.5263(19) _cell_length_b 15.8560(15) _cell_length_c 4.5578(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1483.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6900 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.44 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 12.060 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1332 _exptl_absorpt_correction_T_max 0.3785 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10320 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3079 _reflns_number_gt 2784 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0000P)^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 -0.006(6) _chemical_absolute_configuration ad _refine_ls_number_reflns 3079 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0190 _refine_ls_R_factor_gt 0.0154 _refine_ls_wR_factor_ref 0.0365 _refine_ls_wR_factor_gt 0.0354 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 0.275140(5) 0.082568(7) 0.24741(8) 0.01483(4) Uani 1 1 d . . . Cl1 Cl 0.31619(5) -0.04972(6) 0.5204(2) 0.0239(2) Uani 1 1 d . . . O1 O 0.21487(9) 0.22297(14) 0.2308(12) 0.0162(5) Uani 1 1 d . . . C1 C 0.17939(19) 0.0724(2) 0.5023(8) 0.0157(8) Uani 1 1 d . . . C2 C 0.16489(17) 0.0070(2) 0.6985(11) 0.0176(10) Uani 1 1 d . . . H2 H 0.1976 -0.0324 0.7527 0.021 Uiso 1 1 calc R . . C3 C 0.1017(2) -0.0001(3) 0.8146(7) 0.0217(10) Uani 1 1 d . . . H3 H 0.0916 -0.0445 0.9470 0.026 Uiso 1 1 calc R . . C4 C 0.05434(16) 0.0572(2) 0.7369(15) 0.0202(7) Uani 1 1 d . . . H4 H 0.0118 0.0522 0.8170 0.024 Uiso 1 1 calc R . . C5 C 0.06819(18) 0.1225(3) 0.5419(8) 0.0193(8) Uani 1 1 d . . . H5 H 0.0351 0.1613 0.4866 0.023 Uiso 1 1 calc R . . C6 C 0.13111(19) 0.1305(2) 0.4286(8) 0.0164(8) Uani 1 1 d . . . C7 C 0.14634(15) 0.2019(2) 0.2215(16) 0.0197(8) Uani 1 1 d . . . H7A H 0.1342 0.1854 0.0193 0.024 Uiso 1 1 calc R . . H7B H 0.1203 0.2520 0.2763 0.024 Uiso 1 1 calc R . . C8 C 0.23015(17) 0.2698(2) 0.4978(9) 0.0173(8) Uani 1 1 d . . . H8A H 0.1988 0.2544 0.6540 0.021 Uiso 1 1 calc R . . H8B H 0.2259 0.3311 0.4598 0.021 Uiso 1 1 calc R . . C9 C 0.29805(18) 0.2507(3) 0.5985(8) 0.0160(7) Uani 1 1 d . . . C10 C 0.32882(18) 0.3119(2) 0.7800(12) 0.0178(10) Uani 1 1 d . . . H10 H 0.3063 0.3624 0.8281 0.021 Uiso 1 1 calc R . . C11 C 0.3899(2) 0.2992(3) 0.8856(9) 0.0224(9) Uani 1 1 d . . . H11 H 0.4086 0.3390 1.0164 0.027 Uiso 1 1 calc R . . C12 C 0.42568(18) 0.2270(2) 0.8018(8) 0.0185(10) Uani 1 1 d . . . C13 C 0.4916(2) 0.2144(3) 0.8938(9) 0.0236(9) Uani 1 1 d . . . H13 H 0.5105 0.2528 1.0292 0.028 Uiso 1 1 calc R . . C14 C 0.52795(19) 0.1491(3) 0.7935(10) 0.0242(11) Uani 1 1 d . . . H14 H 0.5719 0.1429 0.8549 0.029 Uiso 1 1 calc R . . C15 C 0.5000(2) 0.0901(3) 0.5962(11) 0.0251(9) Uani 1 1 d . . . H15 H 0.5258 0.0454 0.5206 0.030 Uiso 1 1 calc R . . C16 C 0.43594(19) 0.0972(2) 0.5140(9) 0.0201(8) Uani 1 1 d . . . H16 H 0.4176 0.0562 0.3866 0.024 Uiso 1 1 calc R . . C17 C 0.39652(18) 0.1648(2) 0.6159(8) 0.0143(7) Uani 1 1 d . . . C18 C 0.32981(17) 0.1770(2) 0.5291(8) 0.0148(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 0.01521(6) 0.01590(6) 0.01339(6) -0.00315(12) 0.00014(13) -0.00113(5) Cl1 0.0199(4) 0.0147(4) 0.0372(6) 0.0034(4) 0.0025(4) 0.0022(4) O1 0.0148(10) 0.0193(11) 0.0144(11) -0.003(2) -0.0029(18) -0.0011(8) C1 0.0164(18) 0.0176(19) 0.0131(18) -0.0039(16) 0.0010(15) -0.0065(15) C2 0.0212(17) 0.0136(16) 0.018(3) -0.0054(17) -0.0037(17) -0.0019(13) C3 0.029(2) 0.0205(19) 0.015(2) -0.0013(14) 0.0020(15) -0.0086(17) C4 0.0179(15) 0.0237(17) 0.0189(16) -0.011(4) 0.006(3) -0.0050(13) C5 0.0166(18) 0.026(2) 0.0155(19) -0.0023(17) -0.0030(15) -0.0003(16) C6 0.0189(18) 0.018(2) 0.0119(17) -0.0055(15) -0.0032(15) -0.0037(16) C7 0.0157(14) 0.0248(18) 0.019(2) 0.003(3) -0.001(2) 0.0016(13) C8 0.0222(19) 0.0109(18) 0.019(2) -0.0003(15) -0.0020(16) -0.0013(15) C9 0.0174(17) 0.0156(17) 0.0151(17) 0.0029(16) 0.0000(14) -0.0030(17) C10 0.0213(16) 0.0129(15) 0.019(3) -0.0029(18) 0.0034(19) -0.0007(14) C11 0.026(2) 0.019(2) 0.022(2) -0.0048(17) -0.0038(17) -0.0056(18) C12 0.0202(17) 0.0195(19) 0.016(3) 0.0039(14) -0.0009(14) -0.0012(15) C13 0.023(2) 0.024(2) 0.024(2) -0.0002(18) -0.0097(17) -0.0046(18) C14 0.0200(17) 0.0276(19) 0.025(3) 0.0063(17) -0.0084(18) 0.0016(16) C15 0.023(2) 0.018(2) 0.035(2) 0.0028(19) 0.0013(18) 0.0028(17) C16 0.0184(19) 0.0163(19) 0.026(2) -0.0012(17) -0.0025(17) -0.0014(15) C17 0.0173(18) 0.0115(17) 0.0141(16) 0.0037(15) 0.0010(14) -0.0037(15) C18 0.0176(18) 0.0121(17) 0.0146(17) 0.0021(15) -0.0002(16) 0.0000(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 C18 2.270(4) . ? Bi1 C1 2.289(4) . ? Bi1 O1 2.548(2) . ? Bi1 Cl1 2.5803(10) . ? O1 C7 1.446(4) . ? O1 C8 1.460(6) . ? C1 C6 1.394(5) . ? C1 C2 1.402(6) . ? C2 C3 1.406(5) . ? C2 H2 0.9500 . ? C3 C4 1.376(6) . ? C3 H3 0.9500 . ? C4 C5 1.394(7) . ? C4 H4 0.9500 . ? C5 C6 1.397(5) . ? C5 H5 0.9500 . ? C6 C7 1.507(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.498(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C18 1.375(5) . ? C9 C10 1.422(6) . ? C10 C11 1.358(6) . ? C10 H10 0.9500 . ? C11 C12 1.412(5) . ? C11 H11 0.9500 . ? C12 C13 1.431(5) . ? C12 C17 1.432(5) . ? C13 C14 1.355(6) . ? C13 H13 0.9500 . ? C14 C15 1.418(6) . ? C14 H14 0.9500 . ? C15 C16 1.372(6) . ? C15 H15 0.9500 . ? C16 C17 1.421(5) . ? C16 H16 0.9500 . ? C17 C18 1.438(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 C18 Bi1 C1 100.59(13) . . ? C18 Bi1 O1 71.35(12) . . ? C1 Bi1 O1 70.10(12) . . ? C18 Bi1 Cl1 95.87(9) . . ? C1 Bi1 Cl1 88.77(10) . . ? O1 Bi1 Cl1 152.02(13) . . ? C7 O1 C8 110.5(4) . . ? C7 O1 Bi1 105.73(18) . . ? C8 O1 Bi1 108.4(2) . . ? C6 C1 C2 119.5(3) . . ? C6 C1 Bi1 116.2(3) . . ? C2 C1 Bi1 123.9(3) . . ? C1 C2 C3 119.7(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.7(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.6(4) . . ? C1 C6 C7 120.0(3) . . ? C5 C6 C7 119.4(4) . . ? O1 C7 C6 110.9(4) . . ? O1 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.0 . . ? O1 C8 C9 110.6(3) . . ? O1 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C18 C9 C10 120.2(3) . . ? C18 C9 C8 122.8(3) . . ? C10 C9 C8 117.0(3) . . ? C11 C10 C9 121.0(4) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 121.8(4) . . ? C11 C12 C17 120.1(3) . . ? C13 C12 C17 118.2(4) . . ? C14 C13 C12 121.9(4) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.4(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 121.3(4) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C16 C17 C12 118.4(3) . . ? C16 C17 C18 123.6(3) . . ? C12 C17 C18 117.9(3) . . ? C9 C18 C17 120.2(3) . . ? C9 C18 Bi1 117.2(3) . . ? C17 C18 Bi1 122.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Bi1 O1 C7 -143.8(4) . . . . ? C1 Bi1 O1 C7 -34.7(4) . . . . ? Cl1 Bi1 O1 C7 -77.8(4) . . . . ? C18 Bi1 O1 C8 -25.3(2) . . . . ? C1 Bi1 O1 C8 83.9(3) . . . . ? Cl1 Bi1 O1 C8 40.8(3) . . . . ? C18 Bi1 C1 C6 88.1(3) . . . . ? O1 Bi1 C1 C6 22.5(3) . . . . ? Cl1 Bi1 C1 C6 -176.2(3) . . . . ? C18 Bi1 C1 C2 -99.2(3) . . . . ? O1 Bi1 C1 C2 -164.7(4) . . . . ? Cl1 Bi1 C1 C2 -3.4(3) . . . . ? C6 C1 C2 C3 1.0(6) . . . . ? Bi1 C1 C2 C3 -171.5(3) . . . . ? C1 C2 C3 C4 -0.3(6) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? C3 C4 C5 C6 -1.1(7) . . . . ? C2 C1 C6 C5 -1.8(6) . . . . ? Bi1 C1 C6 C5 171.3(3) . . . . ? C2 C1 C6 C7 179.1(4) . . . . ? Bi1 C1 C6 C7 -7.8(5) . . . . ? C4 C5 C6 C1 1.9(6) . . . . ? C4 C5 C6 C7 -179.1(4) . . . . ? C8 O1 C7 C6 -75.4(4) . . . . ? Bi1 O1 C7 C6 41.7(5) . . . . ? C1 C6 C7 O1 -26.5(6) . . . . ? C5 C6 C7 O1 154.4(4) . . . . ? C7 O1 C8 C9 148.0(3) . . . . ? Bi1 O1 C8 C9 32.6(4) . . . . ? O1 C8 C9 C18 -24.8(5) . . . . ? O1 C8 C9 C10 156.9(4) . . . . ? C18 C9 C10 C11 0.6(6) . . . . ? C8 C9 C10 C11 178.9(4) . . . . ? C9 C10 C11 C12 3.9(7) . . . . ? C10 C11 C12 C13 176.0(4) . . . . ? C10 C11 C12 C17 -3.0(6) . . . . ? C11 C12 C13 C14 -174.1(4) . . . . ? C17 C12 C13 C14 4.8(6) . . . . ? C12 C13 C14 C15 -1.4(7) . . . . ? C13 C14 C15 C16 -2.1(7) . . . . ? C14 C15 C16 C17 2.0(7) . . . . ? C15 C16 C17 C12 1.5(6) . . . . ? C15 C16 C17 C18 177.8(4) . . . . ? C11 C12 C17 C16 174.2(4) . . . . ? C13 C12 C17 C16 -4.8(5) . . . . ? C11 C12 C17 C18 -2.3(5) . . . . ? C13 C12 C17 C18 178.7(3) . . . . ? C10 C9 C18 C17 -6.0(5) . . . . ? C8 C9 C18 C17 175.8(4) . . . . ? C10 C9 C18 Bi1 178.5(3) . . . . ? C8 C9 C18 Bi1 0.3(5) . . . . ? C16 C17 C18 C9 -169.5(4) . . . . ? C12 C17 C18 C9 6.7(5) . . . . ? C16 C17 C18 Bi1 5.7(5) . . . . ? C12 C17 C18 Bi1 -178.0(3) . . . . ? C1 Bi1 C18 C9 -51.2(3) . . . . ? O1 Bi1 C18 C9 13.4(3) . . . . ? Cl1 Bi1 C18 C9 -141.0(3) . . . . ? C1 Bi1 C18 C17 133.4(3) . . . . ? O1 Bi1 C18 C17 -162.0(3) . . . . ? Cl1 Bi1 C18 C17 43.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.585 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.089 data_cd212535 _database_code_depnum_ccdc_archive 'CCDC 909196' #TrackingRef 'cd212535.cif' _audit_update_record ; 2013-02-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Cl S Sb' _chemical_formula_weight 419.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4234(8) _cell_length_b 11.2183(8) _cell_length_c 13.3640(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.4280(10) _cell_angle_gamma 90.00 _cell_volume 1594.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5790 _cell_measurement_theta_min 4.890 _cell_measurement_theta_max 56.566 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.265 _exptl_crystal_size_mid 0.156 _exptl_crystal_size_min 0.132 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 2.019 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6168 _exptl_absorpt_correction_T_max 0.7765 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9412 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3129 _reflns_number_gt 2859 _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^)+(0.0364P)^2^+0.4603P] 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 3129 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Sb1 Sb 0.671616(15) 0.465385(14) 0.770745(13) 0.03808(8) Uani 1 1 d . . . Cl1 Cl 0.67286(7) 0.68601(6) 0.80889(6) 0.05056(18) Uani 1 1 d . . . S1 S 0.57491(7) 0.23855(6) 0.75504(6) 0.05006(18) Uani 1 1 d . . . C1 C 0.4820(3) 0.4821(2) 0.6498(2) 0.0415(6) Uani 1 1 d . . . C2 C 0.4246(3) 0.5926(3) 0.6185(2) 0.0490(7) Uani 1 1 d . . . H2 H 0.4646 0.6607 0.6546 0.059 Uiso 1 1 calc R . . C3 C 0.3100(3) 0.6035(3) 0.5356(3) 0.0605(8) Uani 1 1 d . . . H3 H 0.2736 0.6782 0.5161 0.073 Uiso 1 1 calc R . . C4 C 0.2498(3) 0.5033(4) 0.4816(3) 0.0699(10) Uani 1 1 d . . . H4 H 0.1717 0.5099 0.4264 0.084 Uiso 1 1 calc R . . C5 C 0.3057(3) 0.3927(3) 0.5099(3) 0.0669(9) Uani 1 1 d . . . H5 H 0.2650 0.3251 0.4731 0.080 Uiso 1 1 calc R . . C6 C 0.4212(3) 0.3814(3) 0.5921(2) 0.0497(7) Uani 1 1 d . . . C7 C 0.4793(3) 0.2596(3) 0.6156(3) 0.0587(8) Uani 1 1 d . . . H7A H 0.5306 0.2470 0.5726 0.070 Uiso 1 1 calc R . . H7B H 0.4130 0.2002 0.5945 0.070 Uiso 1 1 calc R . . C8 C 0.4731(3) 0.2871(3) 0.8244(2) 0.0512(7) Uani 1 1 d . . . H8A H 0.4083 0.3400 0.7788 0.061 Uiso 1 1 calc R . . H8B H 0.4328 0.2190 0.8430 0.061 Uiso 1 1 calc R . . C9 C 0.5546(2) 0.3515(2) 0.9244(2) 0.0424(6) Uani 1 1 d . . . C10 C 0.5361(3) 0.3290(3) 1.0216(3) 0.0554(7) Uani 1 1 d . . . H10 H 0.4719 0.2781 1.0216 0.067 Uiso 1 1 calc R . . C11 C 0.6102(3) 0.3802(3) 1.1140(3) 0.0616(8) Uani 1 1 d . . . H11 H 0.5943 0.3666 1.1765 0.074 Uiso 1 1 calc R . . C12 C 0.7110(3) 0.4536(3) 1.1177(2) 0.0523(7) Uani 1 1 d . . . C13 C 0.7964(4) 0.5019(4) 1.2163(3) 0.0692(10) Uani 1 1 d . . . H13 H 0.7817 0.4895 1.2795 0.083 Uiso 1 1 calc R . . C14 C 0.8984(4) 0.5655(3) 1.2192(3) 0.0730(11) Uani 1 1 d . . . H14 H 0.9519 0.5978 1.2838 0.088 Uiso 1 1 calc R . . C15 C 0.9234(3) 0.5826(3) 1.1253(3) 0.0619(9) Uani 1 1 d . . . H15 H 0.9961 0.6226 1.1285 0.074 Uiso 1 1 calc R . . C16 C 0.8424(3) 0.5413(2) 1.0291(3) 0.0497(7) Uani 1 1 d . . . H16 H 0.8595 0.5556 0.9673 0.060 Uiso 1 1 calc R . . C17 C 0.7324(3) 0.4769(2) 1.0211(2) 0.0415(6) Uani 1 1 d . . . C18 C 0.6475(3) 0.4284(2) 0.9225(2) 0.0393(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.03674(12) 0.03725(12) 0.03929(12) -0.00130(7) 0.01275(9) -0.00303(6) Cl1 0.0540(4) 0.0370(3) 0.0535(4) -0.0002(3) 0.0111(3) -0.0092(3) S1 0.0530(4) 0.0357(3) 0.0576(4) -0.0034(3) 0.0156(3) -0.0014(3) C1 0.0419(15) 0.0439(14) 0.0356(14) 0.0000(11) 0.0106(12) -0.0035(12) C2 0.0543(17) 0.0460(15) 0.0423(15) 0.0057(13) 0.0125(13) -0.0028(13) C3 0.0568(19) 0.0647(19) 0.0480(17) 0.0180(15) 0.0050(14) 0.0069(16) C4 0.0509(19) 0.092(2) 0.0466(19) 0.0090(19) -0.0060(15) -0.0020(19) C5 0.064(2) 0.073(2) 0.0469(18) -0.0075(16) 0.0002(15) -0.0173(18) C6 0.0511(16) 0.0532(16) 0.0392(15) -0.0070(13) 0.0099(12) -0.0105(14) C7 0.067(2) 0.0449(15) 0.0535(18) -0.0165(14) 0.0092(15) -0.0094(15) C8 0.0476(16) 0.0467(15) 0.0591(18) 0.0027(14) 0.0193(14) -0.0085(13) C9 0.0396(14) 0.0369(13) 0.0506(15) 0.0064(12) 0.0162(12) 0.0064(11) C10 0.0541(16) 0.0558(17) 0.0644(19) 0.0115(15) 0.0313(15) 0.0041(14) C11 0.071(2) 0.070(2) 0.0529(19) 0.0106(16) 0.0343(17) 0.0141(18) C12 0.0575(19) 0.0524(16) 0.0423(16) 0.0024(12) 0.0127(14) 0.0202(14) C13 0.084(3) 0.072(2) 0.0421(19) -0.0021(17) 0.0125(17) 0.024(2) C14 0.079(3) 0.065(2) 0.047(2) -0.0095(17) -0.0096(18) 0.018(2) C15 0.0564(19) 0.0432(16) 0.064(2) -0.0053(15) -0.0035(16) 0.0045(14) C16 0.0508(17) 0.0373(14) 0.0499(17) 0.0024(12) 0.0053(14) 0.0056(12) C17 0.0418(14) 0.0358(13) 0.0418(15) 0.0020(11) 0.0093(12) 0.0110(11) C18 0.0420(14) 0.0338(12) 0.0412(14) 0.0042(11) 0.0140(11) 0.0049(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 Sb1 C18 2.184(3) . ? Sb1 C1 2.186(3) . ? Sb1 Cl1 2.5260(7) . ? Sb1 S1 2.7515(7) . ? S1 C7 1.799(3) . ? S1 C8 1.815(3) . ? C1 C2 1.393(4) . ? C1 C6 1.401(4) . ? C2 C3 1.377(4) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.501(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.505(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C18 1.375(4) . ? C9 C10 1.411(4) . ? C10 C11 1.344(5) . ? C10 H10 0.9300 . ? C11 C12 1.402(5) . ? C11 H11 0.9300 . ? C12 C17 1.423(4) . ? C12 C13 1.430(5) . ? C13 C14 1.355(6) . ? C13 H13 0.9300 . ? C14 C15 1.399(6) . ? C14 H14 0.9300 . ? C15 C16 1.362(4) . ? C15 H15 0.9300 . ? C16 C17 1.419(4) . ? C16 H16 0.9300 . ? C17 C18 1.428(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 Sb1 C1 106.01(10) . . ? C18 Sb1 Cl1 89.55(7) . . ? C1 Sb1 Cl1 89.78(7) . . ? C18 Sb1 S1 73.24(7) . . ? C1 Sb1 S1 76.19(7) . . ? Cl1 Sb1 S1 153.39(2) . . ? C7 S1 C8 103.28(15) . . ? C7 S1 Sb1 91.87(10) . . ? C8 S1 Sb1 89.86(9) . . ? C2 C1 C6 117.9(3) . . ? C2 C1 Sb1 121.9(2) . . ? C6 C1 Sb1 119.7(2) . . ? C3 C2 C1 121.7(3) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.1(3) . . ? C5 C6 C7 118.1(3) . . ? C1 C6 C7 121.8(3) . . ? C6 C7 S1 113.0(2) . . ? C6 C7 H7A 109.0 . . ? S1 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? S1 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 S1 107.09(19) . . ? C9 C8 H8A 110.3 . . ? S1 C8 H8A 110.3 . . ? C9 C8 H8B 110.3 . . ? S1 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C18 C9 C10 120.3(3) . . ? C18 C9 C8 121.0(2) . . ? C10 C9 C8 118.7(3) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 121.1(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C17 119.2(3) . . ? C11 C12 C13 122.0(3) . . ? C17 C12 C13 118.8(3) . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 121.5(3) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C16 C17 C12 117.8(3) . . ? C16 C17 C18 123.2(3) . . ? C12 C17 C18 118.9(3) . . ? C9 C18 C17 119.4(2) . . ? C9 C18 Sb1 119.8(2) . . ? C17 C18 Sb1 120.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Sb1 S1 C7 142.74(14) . . . . ? C1 Sb1 S1 C7 30.99(14) . . . . ? Cl1 Sb1 S1 C7 91.02(13) . . . . ? C18 Sb1 S1 C8 39.45(12) . . . . ? C1 Sb1 S1 C8 -72.30(13) . . . . ? Cl1 Sb1 S1 C8 -12.27(12) . . . . ? C18 Sb1 C1 C2 96.8(2) . . . . ? Cl1 Sb1 C1 C2 7.3(2) . . . . ? S1 Sb1 C1 C2 164.5(2) . . . . ? C18 Sb1 C1 C6 -91.1(2) . . . . ? Cl1 Sb1 C1 C6 179.5(2) . . . . ? S1 Sb1 C1 C6 -23.4(2) . . . . ? C6 C1 C2 C3 1.7(4) . . . . ? Sb1 C1 C2 C3 174.0(2) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 -1.1(6) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C4 C5 C6 C1 1.5(5) . . . . ? C4 C5 C6 C7 -177.4(3) . . . . ? C2 C1 C6 C5 -2.5(4) . . . . ? Sb1 C1 C6 C5 -175.0(2) . . . . ? C2 C1 C6 C7 176.4(3) . . . . ? Sb1 C1 C6 C7 3.9(4) . . . . ? C5 C6 C7 S1 -148.8(3) . . . . ? C1 C6 C7 S1 32.3(4) . . . . ? C8 S1 C7 C6 50.2(3) . . . . ? Sb1 S1 C7 C6 -40.1(2) . . . . ? C7 S1 C8 C9 -142.14(19) . . . . ? Sb1 S1 C8 C9 -50.25(18) . . . . ? S1 C8 C9 C18 41.3(3) . . . . ? S1 C8 C9 C10 -137.0(2) . . . . ? C18 C9 C10 C11 -1.3(4) . . . . ? C8 C9 C10 C11 177.0(3) . . . . ? C9 C10 C11 C12 -2.6(5) . . . . ? C10 C11 C12 C17 1.9(4) . . . . ? C10 C11 C12 C13 -175.4(3) . . . . ? C11 C12 C13 C14 175.2(3) . . . . ? C17 C12 C13 C14 -2.2(5) . . . . ? C12 C13 C14 C15 -1.5(6) . . . . ? C13 C14 C15 C16 3.5(5) . . . . ? C14 C15 C16 C17 -1.8(4) . . . . ? C15 C16 C17 C12 -1.8(4) . . . . ? C15 C16 C17 C18 -177.7(3) . . . . ? C11 C12 C17 C16 -173.7(3) . . . . ? C13 C12 C17 C16 3.7(4) . . . . ? C11 C12 C17 C18 2.4(4) . . . . ? C13 C12 C17 C18 179.8(3) . . . . ? C10 C9 C18 C17 5.7(4) . . . . ? C8 C9 C18 C17 -172.6(2) . . . . ? C10 C9 C18 Sb1 -178.5(2) . . . . ? C8 C9 C18 Sb1 3.2(3) . . . . ? C16 C17 C18 C9 169.7(2) . . . . ? C12 C17 C18 C9 -6.2(4) . . . . ? C16 C17 C18 Sb1 -6.0(3) . . . . ? C12 C17 C18 Sb1 178.07(18) . . . . ? C1 Sb1 C18 C9 40.7(2) . . . . ? Cl1 Sb1 C18 C9 130.4(2) . . . . ? S1 Sb1 C18 C9 -29.03(18) . . . . ? C1 Sb1 C18 C17 -143.5(2) . . . . ? Cl1 Sb1 C18 C17 -53.86(19) . . . . ? S1 Sb1 C18 C17 146.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.009 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.075 data_cd212520 _database_code_depnum_ccdc_archive 'CCDC 909197' #TrackingRef 'cif 3.cif' _audit_update_record ; 2012-11-05 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 Bi Cl S' _chemical_formula_weight 506.78 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6940(12) _cell_length_b 11.4596(12) _cell_length_c 12.4340(13) _cell_angle_alpha 90.00 _cell_angle_beta 110.526(2) _cell_angle_gamma 90.00 _cell_volume 1560.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4332 _cell_measurement_theta_min 4.987 _cell_measurement_theta_max 56.187 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.165 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 11.593 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.06827 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9015 _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3063 _reflns_number_gt 2598 _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^)+(0.0595P)^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 ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3063 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.13042(2) 0.03405(3) 0.70665(2) 0.03101(16) Uani 1 1 d . . . Cl1 Cl 0.16137(17) -0.19310(19) 0.74904(18) 0.0505(5) Uani 1 1 d . . . S1 S 0.0132(2) 0.25153(18) 0.69214(19) 0.0478(5) Uani 1 1 d . . . C1 C -0.0737(6) -0.0004(7) 0.6117(6) 0.0302(16) Uani 1 1 d . . . C2 C -0.1184(6) -0.1148(7) 0.5973(6) 0.0333(17) Uani 1 1 d . . . H2 H -0.0657 -0.1761 0.6302 0.040 Uiso 1 1 calc R . . C3 C -0.2388(7) -0.1382(8) 0.5354(7) 0.044(2) Uani 1 1 d . . . H3 H -0.2670 -0.2148 0.5252 0.053 Uiso 1 1 calc R . . C4 C -0.3179(8) -0.0464(9) 0.4883(8) 0.053(2) Uani 1 1 d . . . H4 H -0.4002 -0.0613 0.4490 0.064 Uiso 1 1 calc R . . C5 C -0.2752(8) 0.0666(10) 0.4993(8) 0.053(2) Uani 1 1 d . . . H5 H -0.3284 0.1277 0.4665 0.064 Uiso 1 1 calc R . . C6 C -0.1525(7) 0.0890(7) 0.5596(6) 0.0361(17) Uani 1 1 d . . . C7 C -0.1098(8) 0.2140(7) 0.5636(7) 0.051(2) Uani 1 1 d . . . H7A H -0.1782 0.2654 0.5558 0.061 Uiso 1 1 calc R . . H7B H -0.0842 0.2277 0.4984 0.061 Uiso 1 1 calc R . . C8 C -0.0500(7) 0.2078(7) 0.8003(6) 0.0424(19) Uani 1 1 d . . . H8A H -0.0792 0.2764 0.8283 0.051 Uiso 1 1 calc R . . H8B H -0.1192 0.1566 0.7655 0.051 Uiso 1 1 calc R . . C9 C 0.0425(6) 0.1460(7) 0.8998(7) 0.0363(17) Uani 1 1 d . . . C10 C 0.0369(7) 0.1633(8) 1.0100(7) 0.048(2) Uani 1 1 d . . . H10 H -0.0231 0.2123 1.0177 0.057 Uiso 1 1 calc R . . C11 C 0.1140(8) 0.1124(9) 1.1034(8) 0.054(2) Uani 1 1 d . . . H11 H 0.1056 0.1238 1.1743 0.065 Uiso 1 1 calc R . . C12 C 0.2095(8) 0.0404(7) 1.0945(7) 0.042(2) Uani 1 1 d . . . C13 C 0.2983(9) -0.0107(8) 1.1940(7) 0.050(2) Uani 1 1 d . . . H13 H 0.2894 -0.0044 1.2652 0.059 Uiso 1 1 calc R . . C14 C 0.3956(9) -0.0684(9) 1.1840(9) 0.064(3) Uani 1 1 d . . . H14 H 0.4540 -0.1006 1.2487 0.077 Uiso 1 1 calc R . . C15 C 0.4083(7) -0.0793(8) 1.0780(8) 0.048(2) Uani 1 1 d . . . H15 H 0.4775 -0.1154 1.0731 0.058 Uiso 1 1 calc R . . C16 C 0.3227(7) -0.0391(6) 0.9821(7) 0.0364(19) Uani 1 1 d . . . H16 H 0.3320 -0.0517 0.9118 0.044 Uiso 1 1 calc R . . C17 C 0.2184(7) 0.0224(6) 0.9850(6) 0.0308(17) Uani 1 1 d . . . C18 C 0.1302(6) 0.0716(7) 0.8876(6) 0.0336(17) 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 0.0316(2) 0.0264(2) 0.0364(2) -0.00200(11) 0.01363(14) 0.00121(11) Cl1 0.0453(10) 0.0317(11) 0.0558(11) -0.0027(10) -0.0058(9) 0.0082(9) S1 0.0585(12) 0.0206(10) 0.0671(13) 0.0024(10) 0.0256(10) 0.0021(10) C1 0.025(3) 0.034(4) 0.028(4) -0.008(3) 0.006(3) -0.002(3) C2 0.031(3) 0.034(5) 0.033(4) 0.000(3) 0.009(3) -0.001(3) C3 0.044(4) 0.039(5) 0.045(4) -0.006(4) 0.011(3) -0.008(4) C4 0.037(4) 0.061(7) 0.048(5) -0.010(5) 0.000(4) 0.010(4) C5 0.045(5) 0.065(7) 0.042(5) 0.005(5) 0.004(4) 0.025(5) C6 0.043(4) 0.030(4) 0.035(4) 0.004(3) 0.014(3) 0.013(4) C7 0.077(6) 0.028(5) 0.047(4) 0.011(4) 0.020(4) 0.016(5) C8 0.047(4) 0.034(5) 0.047(4) -0.007(4) 0.019(3) 0.009(4) C9 0.036(4) 0.027(4) 0.050(4) -0.013(4) 0.019(3) -0.007(3) C10 0.045(4) 0.042(5) 0.062(5) -0.013(5) 0.026(4) -0.007(4) C11 0.064(5) 0.058(6) 0.048(5) -0.020(5) 0.029(4) -0.019(5) C12 0.046(5) 0.038(5) 0.040(4) -0.010(4) 0.015(4) -0.021(4) C13 0.071(6) 0.038(5) 0.036(5) 0.006(4) 0.015(4) -0.023(5) C14 0.071(7) 0.044(6) 0.050(6) 0.006(5) -0.013(5) -0.017(5) C15 0.044(4) 0.031(5) 0.053(5) 0.004(4) -0.004(4) 0.007(4) C16 0.041(4) 0.022(4) 0.038(4) -0.007(3) 0.004(3) -0.009(3) C17 0.036(4) 0.022(4) 0.032(4) -0.005(3) 0.009(3) -0.015(3) C18 0.039(4) 0.021(4) 0.042(4) -0.007(3) 0.016(3) -0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C18 2.292(7) . ? Bi1 C1 2.296(7) . ? Bi1 Cl1 2.655(2) . ? Bi1 S1 2.819(2) . ? S1 C7 1.788(9) . ? S1 C8 1.817(8) . ? C1 C6 1.379(11) . ? C1 C2 1.400(11) . ? C2 C3 1.373(9) . ? C2 H2 0.9300 . ? C3 C4 1.387(12) . ? C3 H3 0.9300 . ? C4 C5 1.377(14) . ? C4 H4 0.9300 . ? C5 C6 1.391(11) . ? C5 H5 0.9300 . ? C6 C7 1.512(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.505(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C18 1.382(10) . ? C9 C10 1.408(10) . ? C10 C11 1.330(13) . ? C10 H10 0.9300 . ? C11 C12 1.424(12) . ? C11 H11 0.9300 . ? C12 C17 1.415(12) . ? C12 C13 1.433(13) . ? C13 C14 1.358(15) . ? C13 H13 0.9300 . ? C14 C15 1.383(15) . ? C14 H14 0.9300 . ? C15 C16 1.341(11) . ? C15 H15 0.9300 . ? C16 C17 1.421(11) . ? C16 H16 0.9300 . ? C17 C18 1.404(11) . ? 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 C18 Bi1 C1 100.3(3) . . ? C18 Bi1 Cl1 92.1(2) . . ? C1 Bi1 Cl1 88.7(2) . . ? C18 Bi1 S1 74.3(2) . . ? C1 Bi1 S1 74.0(2) . . ? Cl1 Bi1 S1 155.32(7) . . ? C7 S1 C8 100.7(4) . . ? C7 S1 Bi1 93.7(3) . . ? C8 S1 Bi1 91.4(3) . . ? C6 C1 C2 118.5(7) . . ? C6 C1 Bi1 121.1(6) . . ? C2 C1 Bi1 120.1(5) . . ? C3 C2 C1 121.2(7) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 119.3(9) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.4(8) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.8(8) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.7(8) . . ? C1 C6 C7 122.0(7) . . ? C5 C6 C7 117.3(8) . . ? C6 C7 S1 114.2(5) . . ? C6 C7 H7A 108.7 . . ? S1 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? S1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 S1 112.1(5) . . ? C9 C8 H8A 109.2 . . ? S1 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? S1 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C18 C9 C10 118.8(8) . . ? C18 C9 C8 123.2(7) . . ? C10 C9 C8 117.9(7) . . ? C11 C10 C9 122.7(8) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 119.7(8) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C17 C12 C11 118.9(8) . . ? C17 C12 C13 119.7(8) . . ? C11 C12 C13 121.3(8) . . ? C14 C13 C12 119.8(9) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(9) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 121.3(9) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 121.9(8) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C12 119.4(7) . . ? C18 C17 C16 123.7(7) . . ? C12 C17 C16 116.7(7) . . ? C9 C18 C17 120.1(7) . . ? C9 C18 Bi1 118.6(5) . . ? C17 C18 Bi1 121.2(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Bi1 S1 C7 -133.6(4) . . . . ? C1 Bi1 S1 C7 -27.8(4) . . . . ? Cl1 Bi1 S1 C7 -75.1(3) . . . . ? C18 Bi1 S1 C8 -32.8(3) . . . . ? C1 Bi1 S1 C8 73.1(3) . . . . ? Cl1 Bi1 S1 C8 25.7(3) . . . . ? C18 Bi1 C1 C6 89.9(6) . . . . ? Cl1 Bi1 C1 C6 -178.2(6) . . . . ? S1 Bi1 C1 C6 19.7(5) . . . . ? C18 Bi1 C1 C2 -95.6(6) . . . . ? Cl1 Bi1 C1 C2 -3.7(5) . . . . ? S1 Bi1 C1 C2 -165.8(6) . . . . ? C6 C1 C2 C3 -1.7(11) . . . . ? Bi1 C1 C2 C3 -176.4(6) . . . . ? C1 C2 C3 C4 -1.3(12) . . . . ? C2 C3 C4 C5 2.7(13) . . . . ? C3 C4 C5 C6 -1.0(14) . . . . ? C2 C1 C6 C5 3.4(11) . . . . ? Bi1 C1 C6 C5 178.0(6) . . . . ? C2 C1 C6 C7 -175.6(7) . . . . ? Bi1 C1 C6 C7 -1.0(10) . . . . ? C4 C5 C6 C1 -2.1(13) . . . . ? C4 C5 C6 C7 177.0(8) . . . . ? C1 C6 C7 S1 -32.1(10) . . . . ? C5 C6 C7 S1 148.8(7) . . . . ? C8 S1 C7 C6 -53.9(7) . . . . ? Bi1 S1 C7 C6 38.2(6) . . . . ? C7 S1 C8 C9 137.7(6) . . . . ? Bi1 S1 C8 C9 43.6(6) . . . . ? S1 C8 C9 C18 -36.0(10) . . . . ? S1 C8 C9 C10 145.5(6) . . . . ? C18 C9 C10 C11 1.2(13) . . . . ? C8 C9 C10 C11 179.7(8) . . . . ? C9 C10 C11 C12 2.3(14) . . . . ? C10 C11 C12 C17 -1.5(12) . . . . ? C10 C11 C12 C13 176.6(8) . . . . ? C17 C12 C13 C14 5.1(13) . . . . ? C11 C12 C13 C14 -172.9(8) . . . . ? C12 C13 C14 C15 -1.0(14) . . . . ? C13 C14 C15 C16 -3.4(15) . . . . ? C14 C15 C16 C17 3.5(13) . . . . ? C11 C12 C17 C18 -2.7(11) . . . . ? C13 C12 C17 C18 179.2(7) . . . . ? C11 C12 C17 C16 173.2(7) . . . . ? C13 C12 C17 C16 -4.9(10) . . . . ? C15 C16 C17 C18 176.4(8) . . . . ? C15 C16 C17 C12 0.7(11) . . . . ? C10 C9 C18 C17 -5.4(11) . . . . ? C8 C9 C18 C17 176.1(7) . . . . ? C10 C9 C18 Bi1 175.9(6) . . . . ? C8 C9 C18 Bi1 -2.6(10) . . . . ? C12 C17 C18 C9 6.2(11) . . . . ? C16 C17 C18 C9 -169.4(7) . . . . ? C12 C17 C18 Bi1 -175.2(5) . . . . ? C16 C17 C18 Bi1 9.3(10) . . . . ? C1 Bi1 C18 C9 -45.9(6) . . . . ? Cl1 Bi1 C18 C9 -135.0(6) . . . . ? S1 Bi1 C18 C9 24.1(5) . . . . ? C1 Bi1 C18 C17 135.4(6) . . . . ? Cl1 Bi1 C18 C17 46.3(6) . . . . ? S1 Bi1 C18 C17 -154.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.790 _refine_diff_density_min -2.783 _refine_diff_density_rms 0.265