Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Silvestru Cristian' 'Lucia Balazs' 'Hans J. Breunig' 'Olimpiu Stanga' _publ_contact_author_name 'Prof Silvestru Cristian' _publ_contact_author_address ; Chemistry Department Universitatea Babes-Bolyai Str. Arany Janos Nr. 11 Cluj-Napoca RO-3400 ROMANIA ; _publ_contact_author_email CRISTI@CHEM.UBBCLUJ.RO _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Hypervalent 5-Bi-12 Derivatives Containing Dichalcogenoimidodi-phisphinato Ligands. Crystal Structure and Solution Behaviour of [2-(Me2NCH2)C6H4]BiCl[(XPR2)(YPR'2)N] (X, Y = O, S, Se; R, R' = Me, Ph) ; data_cs7 _database_code_CSD 183181 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 Bi Cl N2 O P2 S' _chemical_formula_weight 686.90 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 12.4890(10) _cell_length_b 19.2340(10) _cell_length_c 21.543(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5174.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 89 _cell_measurement_theta_min 2.319 _cell_measurement_theta_max 15.023 _exptl_crystal_description bloks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2672 _exptl_absorpt_coefficient_mu 7.140 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.088 _exptl_absorpt_correction_T_max 0.240 _exptl_absorpt_process_details 'Walker & Stuart, 1983' _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 P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 7205 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.1006 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5868 _reflns_number_gt 3065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0175P)^2^+7.5225P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5868 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.005 _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 0.75504(3) 0.139181(15) 0.594249(13) 0.02228(9) Uani 1 1 d . . . P1 P 0.90965(18) -0.01135(12) 0.59633(12) 0.0229(5) Uani 1 1 d . . . Cl1 Cl 0.5909(2) 0.22501(13) 0.61404(11) 0.0375(6) Uani 1 1 d . . . S1 S 0.6313(2) 0.02326(13) 0.61915(11) 0.0312(6) Uani 1 1 d . . . O1 O 0.8934(5) 0.0595(3) 0.5660(3) 0.0288(15) Uani 1 1 d . . . P2 P 0.7349(2) -0.01176(12) 0.68393(10) 0.0249(5) Uani 1 1 d . . . N1 N 0.8783(6) 0.2216(4) 0.5349(3) 0.0280(18) Uani 1 1 d . . . N2 N 0.8560(6) -0.0218(4) 0.6635(3) 0.0284(18) Uani 1 1 d . . . C2 C 0.7734(8) 0.1632(4) 0.4520(4) 0.027(2) Uani 1 1 d . . . C1 C 0.7039(7) 0.1324(4) 0.4957(4) 0.0228(19) Uani 1 1 d . . . C6 C 0.6081(8) 0.1035(5) 0.4753(4) 0.031(2) Uani 1 1 d . . . H6 H 0.5603 0.0830 0.5043 0.039(8) Uiso 1 1 calc R . . C5 C 0.5820(9) 0.1043(5) 0.4128(4) 0.036(2) Uani 1 1 d . . . H5 H 0.5167 0.0840 0.3991 0.039(8) Uiso 1 1 calc R . . C4 C 0.6496(8) 0.1340(5) 0.3710(4) 0.035(2) Uani 1 1 d . . . H4 H 0.6312 0.1338 0.3282 0.039(8) Uiso 1 1 calc R . . C3 C 0.7449(10) 0.1647(5) 0.3897(4) 0.038(2) Uani 1 1 d . . . H3 H 0.7902 0.1865 0.3601 0.039(8) Uiso 1 1 calc R . . C7 C 0.8809(8) 0.1886(5) 0.4728(4) 0.029(2) Uani 1 1 d . . . H7A H 0.9313 0.1488 0.4739 0.019(16) Uiso 1 1 calc R . . H7B H 0.9083 0.2226 0.4422 0.019(16) Uiso 1 1 calc R . . C8 C 0.8326(8) 0.2913(5) 0.5305(4) 0.034(2) Uani 1 1 d . . . H8A H 0.8248 0.3110 0.5722 0.027(7) Uiso 1 1 calc R . . H8B H 0.7623 0.2888 0.5104 0.027(7) Uiso 1 1 calc R . . H8C H 0.8802 0.3209 0.5058 0.027(7) Uiso 1 1 calc R . . C9 C 0.9833(7) 0.2238(5) 0.5627(4) 0.034(2) Uani 1 1 d . . . H9A H 1.0334 0.2464 0.5342 0.027(7) Uiso 1 1 calc R . . H9B H 1.0076 0.1763 0.5713 0.027(7) Uiso 1 1 calc R . . H9C H 0.9801 0.2501 0.6016 0.027(7) Uiso 1 1 calc R . . C10 C 1.0501(7) -0.0262(5) 0.6060(4) 0.028(2) Uani 1 1 d . . . H10A H 1.0840 -0.0308 0.5652 0.027(7) Uiso 1 1 calc R . . H10B H 1.0611 -0.0691 0.6298 0.027(7) Uiso 1 1 calc R . . H10C H 1.0821 0.0130 0.6284 0.027(7) Uiso 1 1 calc R . . C11 C 0.8621(8) -0.0763(5) 0.5430(4) 0.028(2) Uani 1 1 d . . . H11A H 0.7850 -0.0703 0.5366 0.027(7) Uiso 1 1 calc R . . H11B H 0.8760 -0.1226 0.5602 0.027(7) Uiso 1 1 calc R . . H11C H 0.8995 -0.0714 0.5033 0.027(7) Uiso 1 1 calc R . . C18 C 0.6790(7) -0.0931(4) 0.7121(4) 0.0206(19) Uani 1 1 d . . . C23 C 0.7332(8) -0.1549(5) 0.7011(4) 0.033(2) Uani 1 1 d . . . H23 H 0.7995 -0.1543 0.6794 0.039(8) Uiso 1 1 calc R . . C22 C 0.6908(8) -0.2177(5) 0.7215(4) 0.035(2) Uani 1 1 d . . . H22 H 0.7281 -0.2599 0.7142 0.039(8) Uiso 1 1 calc R . . C21 C 0.5957(9) -0.2182(5) 0.7520(4) 0.037(3) Uani 1 1 d . . . H21 H 0.5668 -0.2610 0.7661 0.039(8) Uiso 1 1 calc R . . C20 C 0.5408(8) -0.1576(5) 0.7627(4) 0.039(3) Uani 1 1 d . . . H20 H 0.4742 -0.1589 0.7841 0.039(8) Uiso 1 1 calc R . . C19 C 0.5810(8) -0.0952(4) 0.7430(4) 0.027(2) Uani 1 1 d . . . H19 H 0.5422 -0.0535 0.7502 0.039(8) Uiso 1 1 calc R . . C12 C 0.7334(9) 0.0485(4) 0.7498(4) 0.030(2) Uani 1 1 d . . . C13 C 0.6538(9) 0.0958(5) 0.7580(4) 0.036(3) Uani 1 1 d . . . H13 H 0.5957 0.0976 0.7296 0.039(8) Uiso 1 1 calc R . . C14 C 0.6576(11) 0.1417(6) 0.8082(5) 0.052(3) Uani 1 1 d . . . H14 H 0.6028 0.1754 0.8134 0.039(8) Uiso 1 1 calc R . . C15 C 0.7402(12) 0.1382(6) 0.8501(5) 0.057(3) Uani 1 1 d . . . H15 H 0.7406 0.1683 0.8851 0.039(8) Uiso 1 1 calc R . . C16 C 0.8208(11) 0.0923(7) 0.8419(6) 0.066(4) Uani 1 1 d . . . H16 H 0.8800 0.0917 0.8696 0.039(8) Uiso 1 1 calc R . . C17 C 0.8159(9) 0.0458(6) 0.7921(4) 0.045(3) Uani 1 1 d . . . H17 H 0.8705 0.0118 0.7874 0.039(8) 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 0.02278(15) 0.02207(13) 0.02198(13) 0.00144(15) 0.0005(2) 0.0026(2) P1 0.0243(11) 0.0200(11) 0.0245(11) 0.0008(11) 0.0057(12) 0.0003(10) Cl1 0.0330(14) 0.0402(15) 0.0393(14) -0.0060(11) -0.0018(12) 0.0176(12) S1 0.0269(13) 0.0340(13) 0.0326(12) 0.0090(12) -0.0019(11) -0.0026(12) O1 0.030(4) 0.021(3) 0.036(3) 0.008(3) 0.015(3) 0.006(3) P2 0.0245(14) 0.0269(11) 0.0234(10) 0.0038(9) 0.0051(12) 0.0033(12) N1 0.023(4) 0.033(5) 0.028(4) -0.001(4) 0.005(4) -0.007(4) N2 0.021(4) 0.039(5) 0.025(4) 0.005(4) 0.006(4) 0.004(4) C2 0.034(6) 0.023(4) 0.024(4) -0.004(3) -0.007(4) 0.013(4) C1 0.034(5) 0.015(4) 0.020(4) 0.001(3) -0.004(4) -0.002(4) C6 0.027(5) 0.028(5) 0.038(5) -0.001(5) -0.003(5) -0.005(5) C5 0.046(6) 0.035(6) 0.029(5) -0.006(5) -0.003(5) -0.010(5) C4 0.039(6) 0.042(6) 0.025(5) -0.005(5) -0.010(4) 0.002(6) C3 0.042(6) 0.043(5) 0.029(4) 0.000(4) 0.013(6) 0.012(7) C7 0.032(5) 0.030(5) 0.025(5) 0.004(4) 0.009(4) 0.000(5) C8 0.036(6) 0.028(5) 0.038(6) 0.005(5) 0.001(5) 0.004(5) C9 0.030(5) 0.033(6) 0.039(6) 0.007(5) -0.010(5) -0.010(5) C10 0.029(5) 0.027(5) 0.028(5) 0.004(4) 0.008(4) -0.005(4) C11 0.034(6) 0.029(5) 0.022(5) 0.001(4) 0.004(4) -0.006(5) C18 0.022(5) 0.022(5) 0.018(4) 0.001(3) -0.001(4) 0.002(4) C23 0.028(6) 0.047(6) 0.025(4) -0.002(4) -0.001(5) 0.007(5) C22 0.049(7) 0.021(5) 0.034(5) 0.003(4) -0.009(5) 0.000(5) C21 0.053(7) 0.039(6) 0.018(5) 0.013(5) -0.012(5) -0.016(6) C20 0.036(6) 0.053(7) 0.027(5) 0.010(5) 0.007(4) -0.002(5) C19 0.030(5) 0.022(5) 0.027(5) 0.007(4) 0.002(4) -0.001(4) C12 0.037(6) 0.020(4) 0.032(4) 0.000(3) 0.009(5) -0.002(5) C13 0.050(7) 0.028(6) 0.029(5) 0.007(4) 0.006(5) 0.011(5) C14 0.078(9) 0.034(6) 0.045(6) 0.008(6) 0.031(7) 0.021(8) C15 0.085(9) 0.037(5) 0.048(6) -0.021(5) 0.011(9) -0.008(10) C16 0.069(9) 0.069(9) 0.058(8) -0.030(7) -0.016(8) 0.005(8) C17 0.053(7) 0.044(7) 0.038(6) -0.010(5) -0.011(6) 0.022(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 C1 2.221(8) . ? Bi1 O1 2.389(6) . ? Bi1 N1 2.553(7) . ? Bi1 Cl1 2.666(2) . ? Bi1 S1 2.765(3) . ? P1 O1 1.524(6) . ? P1 N2 1.608(7) . ? P1 C10 1.790(9) . ? P1 C11 1.797(9) . ? S1 P2 2.018(3) . ? P2 N2 1.588(8) . ? P2 C18 1.818(9) . ? P2 C12 1.833(9) . ? N1 C9 1.442(10) . ? N1 C8 1.460(11) . ? N1 C7 1.481(10) . ? C2 C3 1.388(11) . ? C2 C1 1.411(12) . ? C2 C7 1.497(12) . ? C1 C6 1.392(12) . ? C6 C5 1.384(12) . ? C5 C4 1.361(13) . ? C4 C3 1.388(14) . ? C18 C23 1.389(12) . ? C18 C19 1.393(12) . ? C23 C22 1.390(12) . ? C22 C21 1.358(13) . ? C21 C20 1.372(14) . ? C20 C19 1.367(13) . ? C12 C13 1.358(13) . ? C12 C17 1.377(13) . ? C13 C14 1.397(13) . ? C14 C15 1.372(16) . ? C15 C16 1.351(17) . ? C16 C17 1.398(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 O1 85.8(3) . . ? C1 Bi1 N1 74.4(3) . . ? O1 Bi1 N1 80.5(2) . . ? C1 Bi1 Cl1 88.2(2) . . ? O1 Bi1 Cl1 173.83(16) . . ? N1 Bi1 Cl1 99.15(19) . . ? C1 Bi1 S1 88.7(2) . . ? O1 Bi1 S1 86.34(15) . . ? N1 Bi1 S1 159.21(17) . . ? Cl1 Bi1 S1 92.21(9) . . ? O1 P1 N2 116.3(4) . . ? O1 P1 C10 108.9(4) . . ? N2 P1 C10 106.4(4) . . ? O1 P1 C11 107.7(4) . . ? N2 P1 C11 110.5(4) . . ? C10 P1 C11 106.7(5) . . ? P2 S1 Bi1 92.60(12) . . ? P1 O1 Bi1 124.1(3) . . ? N2 P2 C18 110.7(4) . . ? N2 P2 C12 107.5(5) . . ? C18 P2 C12 106.4(4) . . ? N2 P2 S1 117.4(3) . . ? C18 P2 S1 105.8(3) . . ? C12 P2 S1 108.5(3) . . ? C9 N1 C8 110.9(8) . . ? C9 N1 C7 111.6(8) . . ? C8 N1 C7 110.1(7) . . ? C9 N1 Bi1 111.0(6) . . ? C8 N1 Bi1 111.6(5) . . ? C7 N1 Bi1 101.5(5) . . ? P2 N2 P1 129.1(5) . . ? C3 C2 C1 119.7(9) . . ? C3 C2 C7 120.9(9) . . ? C1 C2 C7 119.2(7) . . ? C6 C1 C2 119.1(8) . . ? C6 C1 Bi1 125.0(7) . . ? C2 C1 Bi1 115.9(6) . . ? C5 C6 C1 120.3(9) . . ? C4 C5 C6 120.1(9) . . ? C5 C4 C3 121.2(8) . . ? C4 C3 C2 119.5(9) . . ? N1 C7 C2 113.0(7) . . ? C23 C18 C19 119.0(8) . . ? C23 C18 P2 119.5(7) . . ? C19 C18 P2 121.5(7) . . ? C18 C23 C22 120.2(9) . . ? C21 C22 C23 119.5(10) . . ? C22 C21 C20 120.9(10) . . ? C19 C20 C21 120.6(9) . . ? C20 C19 C18 119.8(9) . . ? C13 C12 C17 119.1(9) . . ? C13 C12 P2 122.1(8) . . ? C17 C12 P2 118.8(8) . . ? C12 C13 C14 119.9(11) . . ? C15 C14 C13 120.3(11) . . ? C16 C15 C14 120.4(10) . . ? C15 C16 C17 119.1(12) . . ? C12 C17 C16 121.1(11) . . ? 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 C1 Bi1 S1 P2 145.9(2) . . . . ? O1 Bi1 S1 P2 60.00(17) . . . . ? N1 Bi1 S1 P2 110.6(5) . . . . ? Cl1 Bi1 S1 P2 -126.01(12) . . . . ? N2 P1 O1 Bi1 -19.9(6) . . . . ? C10 P1 O1 Bi1 -140.0(4) . . . . ? C11 P1 O1 Bi1 104.7(5) . . . . ? C1 Bi1 O1 P1 -121.9(5) . . . . ? N1 Bi1 O1 P1 163.2(4) . . . . ? Cl1 Bi1 O1 P1 -109.6(13) . . . . ? S1 Bi1 O1 P1 -33.0(4) . . . . ? Bi1 S1 P2 N2 -55.0(4) . . . . ? Bi1 S1 P2 C18 -179.1(3) . . . . ? Bi1 S1 P2 C12 67.1(3) . . . . ? C1 Bi1 N1 C9 -147.3(7) . . . . ? O1 Bi1 N1 C9 -59.0(6) . . . . ? Cl1 Bi1 N1 C9 127.2(6) . . . . ? S1 Bi1 N1 C9 -110.5(7) . . . . ? C1 Bi1 N1 C8 88.5(6) . . . . ? O1 Bi1 N1 C8 176.8(6) . . . . ? Cl1 Bi1 N1 C8 3.0(6) . . . . ? S1 Bi1 N1 C8 125.3(6) . . . . ? C1 Bi1 N1 C7 -28.6(5) . . . . ? O1 Bi1 N1 C7 59.6(5) . . . . ? Cl1 Bi1 N1 C7 -114.1(5) . . . . ? S1 Bi1 N1 C7 8.2(9) . . . . ? C18 P2 N2 P1 118.4(6) . . . . ? C12 P2 N2 P1 -125.7(6) . . . . ? S1 P2 N2 P1 -3.1(8) . . . . ? O1 P1 N2 P2 55.2(8) . . . . ? C10 P1 N2 P2 176.7(6) . . . . ? C11 P1 N2 P2 -67.8(8) . . . . ? C3 C2 C1 C6 0.6(13) . . . . ? C7 C2 C1 C6 -174.5(8) . . . . ? C3 C2 C1 Bi1 -176.5(6) . . . . ? C7 C2 C1 Bi1 8.4(10) . . . . ? O1 Bi1 C1 C6 113.5(8) . . . . ? N1 Bi1 C1 C6 -165.2(8) . . . . ? Cl1 Bi1 C1 C6 -65.1(7) . . . . ? S1 Bi1 C1 C6 27.1(7) . . . . ? O1 Bi1 C1 C2 -69.5(6) . . . . ? N1 Bi1 C1 C2 11.8(6) . . . . ? Cl1 Bi1 C1 C2 111.8(6) . . . . ? S1 Bi1 C1 C2 -155.9(6) . . . . ? C2 C1 C6 C5 0.6(14) . . . . ? Bi1 C1 C6 C5 177.5(7) . . . . ? C1 C6 C5 C4 -0.6(15) . . . . ? C6 C5 C4 C3 -0.7(15) . . . . ? C5 C4 C3 C2 1.9(15) . . . . ? C1 C2 C3 C4 -1.8(14) . . . . ? C7 C2 C3 C4 173.1(9) . . . . ? C9 N1 C7 C2 160.2(8) . . . . ? C8 N1 C7 C2 -76.3(9) . . . . ? Bi1 N1 C7 C2 42.0(8) . . . . ? C3 C2 C7 N1 146.3(8) . . . . ? C1 C2 C7 N1 -38.7(11) . . . . ? N2 P2 C18 C23 -13.8(8) . . . . ? C12 P2 C18 C23 -130.3(7) . . . . ? S1 P2 C18 C23 114.4(7) . . . . ? N2 P2 C18 C19 168.3(7) . . . . ? C12 P2 C18 C19 51.7(8) . . . . ? S1 P2 C18 C19 -63.6(7) . . . . ? C19 C18 C23 C22 -1.1(13) . . . . ? P2 C18 C23 C22 -179.1(7) . . . . ? C18 C23 C22 C21 0.4(14) . . . . ? C23 C22 C21 C20 0.2(14) . . . . ? C22 C21 C20 C19 -0.1(15) . . . . ? C21 C20 C19 C18 -0.5(14) . . . . ? C23 C18 C19 C20 1.1(13) . . . . ? P2 C18 C19 C20 179.1(7) . . . . ? N2 P2 C12 C13 144.1(8) . . . . ? C18 P2 C12 C13 -97.2(8) . . . . ? S1 P2 C12 C13 16.2(9) . . . . ? N2 P2 C12 C17 -35.5(9) . . . . ? C18 P2 C12 C17 83.1(9) . . . . ? S1 P2 C12 C17 -163.5(7) . . . . ? C17 C12 C13 C14 1.2(15) . . . . ? P2 C12 C13 C14 -178.5(8) . . . . ? C12 C13 C14 C15 -1.4(17) . . . . ? C13 C14 C15 C16 2.6(19) . . . . ? C14 C15 C16 C17 -4(2) . . . . ? C13 C12 C17 C16 -2.1(17) . . . . ? P2 C12 C17 C16 177.6(9) . . . . ? C15 C16 C17 C12 3.3(19) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.809 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.179 data_cs1 _database_code_CSD 186865 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H32 Bi Cl N2 P2 S2' _chemical_formula_weight 827.10 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' P P 0.1023 0.0942 '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 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 15.121(3) _cell_length_b 11.3420(10) _cell_length_c 20.027(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.470(10) _cell_angle_gamma 90.00 _cell_volume 3276.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 81 _cell_measurement_theta_min 4.809 _cell_measurement_theta_max 17.319 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 5.714 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.099 _exptl_absorpt_correction_T_max 0.152 _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 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -9800.00 _diffrn_reflns_number 7528 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 26.50 _reflns_number_total 5864 _reflns_number_gt 4234 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+2.3148P] 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 0.00023(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5864 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.359135(18) 0.88028(2) 0.442176(13) 0.02203(10) Uani 1 1 d . . . Cl1 Cl 0.54126(12) 0.86811(17) 0.46082(10) 0.0324(4) Uani 1 1 d . . . P1 P 0.13558(12) 1.00412(16) 0.36839(9) 0.0214(4) Uani 1 1 d . . . P2 P 0.24704(13) 1.00533(16) 0.27269(9) 0.0227(4) Uani 1 1 d . . . S1 S 0.16480(13) 0.84027(16) 0.40845(9) 0.0281(4) Uani 1 1 d . . . S2 S 0.32609(14) 0.85969(17) 0.29612(9) 0.0337(5) Uani 1 1 d . . . N2 N 0.2066(4) 1.0578(5) 0.3319(3) 0.0227(13) Uani 1 1 d . . . C10 C 0.1404(5) 1.1034(6) 0.4397(3) 0.0229(15) Uani 1 1 d . . . C15 C 0.0715(5) 1.0993(7) 0.4733(4) 0.0326(18) Uani 1 1 d . . . H15 H 0.0172 1.0534 0.4543 0.038(5) Uiso 1 1 calc R . . C14 C 0.0830(6) 1.1626(8) 0.5342(4) 0.041(2) Uani 1 1 d . . . H14 H 0.0361 1.1604 0.5568 0.038(5) Uiso 1 1 calc R . . C13 C 0.1609(5) 1.2283(7) 0.5623(4) 0.039(2) Uani 1 1 d . . . H13 H 0.1692 1.2702 0.6048 0.038(5) Uiso 1 1 calc R . . C12 C 0.2263(6) 1.2326(7) 0.5284(4) 0.0377(19) Uani 1 1 d . . . H12 H 0.2806 1.2782 0.5481 0.038(5) Uiso 1 1 calc R . . C11 C 0.2172(5) 1.1736(6) 0.4666(4) 0.0315(17) Uani 1 1 d . . . H11 H 0.2628 1.1812 0.4430 0.038(5) Uiso 1 1 calc R . . C16 C 0.0182(5) 1.0012(6) 0.3100(3) 0.0250(16) Uani 1 1 d . . . C17 C -0.0154(5) 0.8980(6) 0.2724(4) 0.0314(17) Uani 1 1 d . . . H17 H 0.0201 0.8275 0.2828 0.038(5) Uiso 1 1 calc R . . C18 C -0.0997(6) 0.8976(8) 0.2202(4) 0.046(2) Uani 1 1 d . . . H18 H -0.1221 0.8279 0.1943 0.038(5) Uiso 1 1 calc R . . C19 C -0.1507(6) 1.0013(8) 0.2066(4) 0.044(2) Uani 1 1 d . . . H19 H -0.2080 1.0021 0.1702 0.038(5) Uiso 1 1 calc R . . C20 C -0.1202(5) 1.1044(7) 0.2446(4) 0.0374(19) Uani 1 1 d . . . H20 H -0.1571 1.1738 0.2358 0.038(5) Uiso 1 1 calc R . . C21 C -0.0347(5) 1.1030(7) 0.2958(4) 0.0320(18) Uani 1 1 d . . . H21 H -0.0122 1.1729 0.3214 0.038(5) Uiso 1 1 calc R . . C28 C 0.3133(5) 1.1224(7) 0.2501(3) 0.0265(15) Uani 1 1 d . . . C29 C 0.3730(5) 1.0970(7) 0.2110(4) 0.037(2) Uani 1 1 d . . . H29 H 0.3823 1.0177 0.1993 0.038(5) Uiso 1 1 calc R . . C30 C 0.4190(6) 1.1885(8) 0.1893(4) 0.044(2) Uani 1 1 d . . . H30 H 0.4586 1.1707 0.1618 0.038(5) Uiso 1 1 calc R . . C31 C 0.4091(6) 1.3022(8) 0.2061(4) 0.043(2) Uani 1 1 d . . . H31 H 0.4420 1.3632 0.1913 0.038(5) Uiso 1 1 calc R . . C32 C 0.3506(6) 1.3280(7) 0.2449(4) 0.042(2) Uani 1 1 d . . . H32 H 0.3425 1.4076 0.2566 0.038(5) Uiso 1 1 calc R . . C33 C 0.3032(6) 1.2385(7) 0.2672(4) 0.0362(19) Uani 1 1 d . . . H33 H 0.2634 1.2575 0.2945 0.038(5) Uiso 1 1 calc R . . C22 C 0.1539(5) 0.9786(7) 0.1927(3) 0.0293(17) Uani 1 1 d . . . C23 C 0.1467(6) 0.8745(8) 0.1549(4) 0.0380(18) Uani 1 1 d . . . H23 H 0.1932 0.8156 0.1691 0.038(5) Uiso 1 1 calc R . . C24 C 0.0709(7) 0.8571(8) 0.0961(4) 0.052(3) Uani 1 1 d . . . H24 H 0.0662 0.7865 0.0697 0.038(5) Uiso 1 1 calc R . . C25 C 0.0026(6) 0.9411(9) 0.0759(4) 0.052(3) Uani 1 1 d . . . H25 H -0.0496 0.9275 0.0362 0.038(5) Uiso 1 1 calc R . . C26 C 0.0092(6) 1.0435(9) 0.1123(4) 0.046(2) Uani 1 1 d . . . H26 H -0.0381 1.1015 0.0979 0.038(5) Uiso 1 1 calc R . . C27 C 0.0849(5) 1.0632(7) 0.1704(4) 0.0341(19) Uani 1 1 d . . . H27 H 0.0898 1.1354 0.1953 0.038(5) Uiso 1 1 calc R . . N1 N 0.3597(4) 0.8285(5) 0.5664(3) 0.0306(15) Uani 1 1 d . . . C1 C 0.3646(5) 0.6828(6) 0.4504(4) 0.0279(17) Uani 1 1 d . . . C2 C 0.3466(5) 0.6339(6) 0.5092(4) 0.0322(17) Uani 1 1 d . . . C3 C 0.3548(6) 0.5121(7) 0.5189(4) 0.041(2) Uani 1 1 d . . . H3 H 0.3425 0.4778 0.5584 0.038(5) Uiso 1 1 calc R . . C4 C 0.3802(6) 0.4410(7) 0.4725(4) 0.042(2) Uani 1 1 d . . . H4 H 0.3855 0.3583 0.4803 0.038(5) Uiso 1 1 calc R . . C5 C 0.3982(5) 0.4887(7) 0.4150(4) 0.037(2) Uani 1 1 d . . . H5 H 0.4164 0.4394 0.3831 0.038(5) Uiso 1 1 calc R . . C6 C 0.3895(5) 0.6100(7) 0.4037(4) 0.0294(17) Uani 1 1 d . . . H6 H 0.4009 0.6429 0.3634 0.038(5) Uiso 1 1 calc R . . C7 C 0.3162(6) 0.7131(6) 0.5588(4) 0.0370(19) Uani 1 1 d . . . H7A H 0.2480 0.7229 0.5414 0.020(12) Uiso 1 1 calc R . . H7B H 0.3315 0.6748 0.6053 0.020(12) Uiso 1 1 calc R . . C8 C 0.4575(6) 0.8220(7) 0.6111(4) 0.042(2) Uani 1 1 d . . . H8A H 0.4601 0.7867 0.6563 0.029(8) Uiso 1 1 calc R . . H8B H 0.4839 0.9016 0.6186 0.029(8) Uiso 1 1 calc R . . H8C H 0.4932 0.7735 0.5879 0.029(8) Uiso 1 1 calc R . . C9 C 0.3076(6) 0.9152(7) 0.5951(4) 0.041(2) Uani 1 1 d . . . H9A H 0.2451 0.9249 0.5624 0.029(8) Uiso 1 1 calc R . . H9B H 0.3399 0.9912 0.6016 0.029(8) Uiso 1 1 calc R . . H9C H 0.3031 0.8870 0.6402 0.029(8) 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 0.02281(14) 0.01767(13) 0.02398(12) 0.00190(14) 0.00453(8) 0.00000(15) Cl1 0.0236(9) 0.0251(9) 0.0472(10) -0.0046(9) 0.0088(7) -0.0011(9) P1 0.0204(9) 0.0206(9) 0.0233(8) 0.0019(7) 0.0068(7) -0.0018(8) P2 0.0247(10) 0.0224(9) 0.0211(8) 0.0015(7) 0.0072(7) -0.0013(8) S1 0.0252(9) 0.0223(8) 0.0349(9) 0.0054(7) 0.0062(8) -0.0004(8) S2 0.0425(11) 0.0319(11) 0.0279(8) 0.0025(8) 0.0123(8) 0.0129(10) N2 0.030(3) 0.019(3) 0.020(3) -0.001(2) 0.007(2) 0.001(3) C10 0.027(4) 0.017(4) 0.024(3) -0.002(3) 0.005(3) -0.006(3) C15 0.029(4) 0.037(5) 0.035(4) -0.001(3) 0.016(3) -0.009(4) C14 0.049(5) 0.049(5) 0.031(4) 0.000(4) 0.024(4) 0.001(5) C13 0.049(5) 0.039(4) 0.027(4) -0.014(4) 0.011(4) 0.005(4) C12 0.037(5) 0.034(4) 0.041(4) -0.016(4) 0.009(4) -0.009(4) C11 0.034(4) 0.030(4) 0.035(4) 0.000(3) 0.015(3) -0.012(4) C16 0.020(4) 0.028(4) 0.027(3) 0.004(3) 0.007(3) 0.001(3) C17 0.029(4) 0.025(4) 0.036(4) -0.001(3) 0.005(3) 0.004(4) C18 0.040(5) 0.046(6) 0.046(5) -0.013(4) 0.004(4) -0.007(5) C19 0.030(4) 0.055(6) 0.039(4) 0.006(4) -0.001(3) -0.004(5) C20 0.030(4) 0.038(5) 0.043(4) 0.005(4) 0.010(3) 0.011(4) C21 0.034(4) 0.029(4) 0.029(3) -0.003(3) 0.003(3) 0.003(4) C28 0.027(4) 0.031(4) 0.019(3) 0.004(3) 0.003(3) -0.006(4) C29 0.041(5) 0.043(5) 0.034(4) -0.005(4) 0.020(4) -0.003(4) C30 0.038(5) 0.066(6) 0.035(4) 0.001(4) 0.024(4) -0.007(5) C31 0.048(5) 0.044(5) 0.036(4) 0.011(4) 0.011(4) -0.017(5) C32 0.057(6) 0.027(4) 0.044(5) 0.008(4) 0.017(4) -0.003(4) C33 0.044(5) 0.039(5) 0.032(4) 0.004(4) 0.022(4) 0.001(4) C22 0.038(4) 0.032(4) 0.020(3) 0.005(3) 0.012(3) -0.008(4) C23 0.046(5) 0.035(4) 0.033(4) -0.003(4) 0.012(3) -0.007(5) C24 0.074(7) 0.052(6) 0.033(4) -0.018(4) 0.018(4) -0.034(6) C25 0.048(5) 0.072(7) 0.027(4) 0.004(5) -0.004(4) -0.024(6) C26 0.032(4) 0.066(6) 0.034(4) 0.012(4) 0.004(4) -0.004(5) C27 0.040(5) 0.035(4) 0.028(4) 0.006(3) 0.011(3) -0.006(4) N1 0.040(4) 0.022(3) 0.027(3) 0.000(3) 0.006(3) -0.002(3) C1 0.028(4) 0.018(3) 0.032(4) 0.003(3) 0.000(3) 0.002(3) C2 0.039(4) 0.021(4) 0.033(4) 0.005(3) 0.005(3) -0.003(4) C3 0.053(5) 0.026(4) 0.044(5) 0.010(4) 0.013(4) -0.006(4) C4 0.047(5) 0.021(4) 0.054(5) 0.008(4) 0.008(4) -0.001(4) C5 0.033(5) 0.024(4) 0.050(5) -0.012(4) 0.005(4) 0.011(4) C6 0.026(4) 0.027(4) 0.034(4) 0.003(4) 0.007(3) 0.001(4) C7 0.049(5) 0.027(4) 0.033(4) 0.004(3) 0.009(4) 0.003(4) C8 0.046(5) 0.042(5) 0.029(4) 0.009(4) -0.003(4) 0.002(4) C9 0.054(5) 0.037(5) 0.033(4) 0.004(3) 0.015(4) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.245(7) . ? Bi1 N1 2.553(6) . ? Bi1 Cl1 2.6693(18) . ? Bi1 S2 2.8254(18) . ? Bi1 S1 2.8470(19) . ? P1 N2 1.590(6) . ? P1 C10 1.803(7) . ? P1 C16 1.809(7) . ? P1 S1 2.020(3) . ? P2 N2 1.604(6) . ? P2 C28 1.801(7) . ? P2 C22 1.812(7) . ? P2 S2 2.010(3) . ? C10 C11 1.377(10) . ? C10 C15 1.400(10) . ? C15 C14 1.380(10) . ? C14 C13 1.363(11) . ? C13 C12 1.359(11) . ? C12 C11 1.378(10) . ? C16 C21 1.385(10) . ? C16 C17 1.402(10) . ? C17 C18 1.385(10) . ? C18 C19 1.388(12) . ? C19 C20 1.397(11) . ? C20 C21 1.387(10) . ? C28 C33 1.381(11) . ? C28 C29 1.390(10) . ? C29 C30 1.390(11) . ? C30 C31 1.352(12) . ? C31 C32 1.371(12) . ? C32 C33 1.392(11) . ? C22 C27 1.390(10) . ? C22 C23 1.390(10) . ? C23 C24 1.388(11) . ? C24 C25 1.373(13) . ? C25 C26 1.359(13) . ? C26 C27 1.384(10) . ? N1 C7 1.452(9) . ? N1 C9 1.481(10) . ? N1 C8 1.483(9) . ? C1 C6 1.383(10) . ? C1 C2 1.400(10) . ? C2 C3 1.395(10) . ? C2 C7 1.510(11) . ? C3 C4 1.368(12) . ? C4 C5 1.371(11) . ? C5 C6 1.394(10) . ? 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 73.1(2) . . ? C1 Bi1 Cl1 85.7(2) . . ? N1 Bi1 Cl1 98.64(15) . . ? C1 Bi1 S2 89.12(19) . . ? N1 Bi1 S2 159.61(14) . . ? Cl1 Bi1 S2 89.71(6) . . ? C1 Bi1 S1 82.59(19) . . ? N1 Bi1 S1 84.02(15) . . ? Cl1 Bi1 S1 166.65(6) . . ? S2 Bi1 S1 83.80(6) . . ? N2 P1 C10 104.6(3) . . ? N2 P1 C16 112.1(3) . . ? C10 P1 C16 108.8(3) . . ? N2 P1 S1 115.9(2) . . ? C10 P1 S1 107.9(2) . . ? C16 P1 S1 107.2(3) . . ? N2 P2 C28 106.1(3) . . ? N2 P2 C22 110.4(3) . . ? C28 P2 C22 104.1(3) . . ? N2 P2 S2 117.7(2) . . ? C28 P2 S2 109.1(3) . . ? C22 P2 S2 108.6(3) . . ? P1 S1 Bi1 91.99(8) . . ? P2 S2 Bi1 94.68(8) . . ? P1 N2 P2 131.1(4) . . ? C11 C10 C15 119.6(6) . . ? C11 C10 P1 119.9(6) . . ? C15 C10 P1 120.1(5) . . ? C14 C15 C10 119.4(7) . . ? C13 C14 C15 120.9(8) . . ? C12 C13 C14 118.8(7) . . ? C13 C12 C11 122.6(7) . . ? C10 C11 C12 118.5(7) . . ? C21 C16 C17 119.5(6) . . ? C21 C16 P1 120.8(5) . . ? C17 C16 P1 119.3(5) . . ? C18 C17 C16 120.7(7) . . ? C17 C18 C19 118.5(8) . . ? C18 C19 C20 122.0(7) . . ? C21 C20 C19 118.3(7) . . ? C16 C21 C20 121.0(7) . . ? C33 C28 C29 118.5(7) . . ? C33 C28 P2 121.9(6) . . ? C29 C28 P2 119.5(6) . . ? C28 C29 C30 119.4(8) . . ? C31 C30 C29 122.1(8) . . ? C30 C31 C32 118.8(8) . . ? C31 C32 C33 120.6(8) . . ? C28 C33 C32 120.6(7) . . ? C27 C22 C23 118.9(7) . . ? C27 C22 P2 118.5(6) . . ? C23 C22 P2 122.5(6) . . ? C24 C23 C22 119.6(8) . . ? C25 C24 C23 120.5(8) . . ? C26 C25 C24 120.5(8) . . ? C25 C26 C27 119.9(9) . . ? C26 C27 C22 120.7(8) . . ? C7 N1 C9 111.2(6) . . ? C7 N1 C8 110.9(6) . . ? C9 N1 C8 110.4(6) . . ? C7 N1 Bi1 103.7(4) . . ? C9 N1 Bi1 112.3(4) . . ? C8 N1 Bi1 108.1(5) . . ? C6 C1 C2 119.6(6) . . ? C6 C1 Bi1 123.9(5) . . ? C2 C1 Bi1 116.4(5) . . ? C3 C2 C1 118.5(7) . . ? C3 C2 C7 122.0(7) . . ? C1 C2 C7 119.5(6) . . ? C4 C3 C2 121.4(8) . . ? C3 C4 C5 120.3(7) . . ? C4 C5 C6 119.6(8) . . ? C1 C6 C5 120.7(7) . . ? N1 C7 C2 112.7(7) . . ? _diffrn_measured_fraction_theta_max 0.779 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.779 _refine_diff_density_max 1.240 _refine_diff_density_min -0.847 _refine_diff_density_rms 0.138 data_cs5 _database_code_CSD 186866 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H32 Bi Cl N2 P2 Se2' _chemical_formula_weight 920.90 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' P P 0.1023 0.0942 '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' Se Se -0.0929 2.2259 '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 Monoclin _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 12.111(3) _cell_length_b 14.046(3) _cell_length_c 20.102(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.60(2) _cell_angle_gamma 90.00 _cell_volume 3323.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 7.697 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.246 _exptl_absorpt_correction_T_max 0.705 _exptl_absorpt_process_details 'Walker & Stuart, 1983' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 8766 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.1045 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7091 _reflns_number_gt 4681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^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 refU _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00018(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7091 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.46756(3) 0.43998(2) 0.107636(17) 0.02624(11) Uani 1 1 d . . . Se1 Se 0.40014(8) 0.48042(6) 0.24017(5) 0.0325(2) Uani 1 1 d . . . Se2 Se 0.67823(8) 0.36838(6) 0.19184(6) 0.0390(3) Uani 1 1 d . . . P1 P 0.51591(18) 0.59958(15) 0.25323(11) 0.0231(5) Uani 1 1 d . . . P2 P 0.72269(19) 0.50602(15) 0.24050(12) 0.0253(5) Uani 1 1 d . . . Cl1 Cl 0.5218(2) 0.35977(17) 0.00050(13) 0.0440(6) Uani 1 1 d . . . N2 N 0.6281(6) 0.5855(4) 0.2248(3) 0.0230(15) Uani 1 1 d . . . N1 N 0.2575(6) 0.4674(5) 0.0476(4) 0.0335(18) Uani 1 1 d . . . C1 C 0.3740(7) 0.3024(6) 0.1160(4) 0.0260(19) Uani 1 1 d . . . C2 C 0.2566(8) 0.3073(6) 0.0962(5) 0.032(2) Uani 1 1 d . . . C3 C 0.1964(8) 0.2223(6) 0.0961(5) 0.036(2) Uani 1 1 d . . . H3 H 0.1159 0.2226 0.0816 0.043(7) Uiso 1 1 calc R . . C4 C 0.2515(9) 0.1394(6) 0.1163(5) 0.040(2) Uani 1 1 d . . . H4 H 0.2086 0.0830 0.1172 0.043(7) Uiso 1 1 calc R . . C5 C 0.3679(9) 0.1354(6) 0.1354(5) 0.040(2) Uani 1 1 d . . . H5 H 0.4057 0.0766 0.1484 0.043(7) Uiso 1 1 calc R . . C6 C 0.4288(8) 0.2179(6) 0.1353(5) 0.033(2) Uani 1 1 d . . . H6 H 0.5094 0.2164 0.1488 0.043(7) Uiso 1 1 calc R . . C10 C 0.4447(7) 0.7020(6) 0.2093(4) 0.0257(19) Uani 1 1 d . . . C11 C 0.4877(8) 0.7500(6) 0.1609(4) 0.031(2) Uani 1 1 d . . . H11 H 0.5561 0.7295 0.1501 0.043(7) Uiso 1 1 calc R . . C12 C 0.4295(9) 0.8283(7) 0.1286(5) 0.049(3) Uani 1 1 d . . . H12 H 0.4580 0.8608 0.0947 0.043(7) Uiso 1 1 calc R . . C13 C 0.3334(9) 0.8595(7) 0.1439(6) 0.051(3) Uani 1 1 d . . . H13 H 0.2959 0.9141 0.1214 0.043(7) Uiso 1 1 calc R . . C14 C 0.2887(8) 0.8125(7) 0.1922(5) 0.046(3) Uani 1 1 d . . . H14 H 0.2207 0.8344 0.2030 0.043(7) Uiso 1 1 calc R . . C15 C 0.3447(8) 0.7331(7) 0.2247(5) 0.040(2) Uani 1 1 d . . . H15 H 0.3147 0.6998 0.2577 0.043(7) Uiso 1 1 calc R . . C16 C 0.5533(7) 0.6344(6) 0.3426(4) 0.0257(19) Uani 1 1 d . . . C17 C 0.5985(8) 0.7237(7) 0.3585(5) 0.039(2) Uani 1 1 d . . . H17 H 0.6032 0.7659 0.3224 0.043(7) Uiso 1 1 calc R . . C18 C 0.6366(9) 0.7536(7) 0.4243(5) 0.050(3) Uani 1 1 d . . . H18 H 0.6669 0.8158 0.4338 0.043(7) Uiso 1 1 calc R . . C19 C 0.6305(9) 0.6919(8) 0.4773(6) 0.053(3) Uani 1 1 d . . . H19 H 0.6560 0.7120 0.5235 0.043(7) Uiso 1 1 calc R . . C20 C 0.5866(8) 0.5998(7) 0.4627(5) 0.043(2) Uani 1 1 d . . . H20 H 0.5839 0.5566 0.4987 0.043(7) Uiso 1 1 calc R . . C21 C 0.5476(7) 0.5732(7) 0.3958(5) 0.033(2) Uani 1 1 d . . . H21 H 0.5160 0.5115 0.3856 0.043(7) Uiso 1 1 calc R . . C22 C 0.7758(7) 0.4878(6) 0.3316(4) 0.030(2) Uani 1 1 d . . . C23 C 0.8232(7) 0.5683(7) 0.3694(4) 0.035(2) Uani 1 1 d . . . H23 H 0.8284 0.6267 0.3465 0.043(7) Uiso 1 1 calc R . . C24 C 0.8617(8) 0.5631(8) 0.4389(5) 0.052(3) Uani 1 1 d . . . H24 H 0.8938 0.6174 0.4644 0.043(7) Uiso 1 1 calc R . . C25 C 0.8535(9) 0.4788(9) 0.4711(6) 0.054(3) Uani 1 1 d . . . H25 H 0.8799 0.4751 0.5194 0.043(7) Uiso 1 1 calc R . . C26 C 0.8084(10) 0.3999(9) 0.4357(6) 0.059(3) Uani 1 1 d . . . H26 H 0.8051 0.3419 0.4594 0.043(7) Uiso 1 1 calc R . . C27 C 0.7674(9) 0.4034(7) 0.3654(6) 0.047(3) Uani 1 1 d . . . H27 H 0.7340 0.3487 0.3409 0.032(10) Uiso 1 1 calc R . . C28 C 0.8428(7) 0.5527(6) 0.2130(4) 0.0265(19) Uani 1 1 d . . . C29 C 0.8440(8) 0.6472(6) 0.1925(5) 0.038(2) Uani 1 1 d . . . H29 H 0.7798 0.6867 0.1909 0.032(10) Uiso 1 1 calc R . . C30 C 0.9401(9) 0.6836(7) 0.1744(6) 0.051(3) Uani 1 1 d . . . H30 H 0.9398 0.7476 0.1591 0.032(10) Uiso 1 1 calc R . . C31 C 1.0317(9) 0.6303(8) 0.1783(5) 0.048(3) Uani 1 1 d . . . H31 H 1.0969 0.6564 0.1665 0.032(10) Uiso 1 1 calc R . . C32 C 1.0323(8) 0.5362(8) 0.1996(5) 0.048(3) Uani 1 1 d . . . H32 H 1.0980 0.4982 0.2021 0.032(10) Uiso 1 1 calc R . . C33 C 0.9400(8) 0.4978(6) 0.2171(5) 0.036(2) Uani 1 1 d . . . H33 H 0.9417 0.4336 0.2320 0.032(10) Uiso 1 1 calc R . . C7 C 0.1951(8) 0.3995(6) 0.0815(5) 0.038(2) Uani 1 1 d . . . H7A H 0.1188 0.3880 0.0516 0.022(15) Uiso 1 1 calc R . . H7B H 0.1851 0.4276 0.1248 0.022(15) Uiso 1 1 calc R . . C8 C 0.2406(8) 0.4472(7) -0.0251(5) 0.046(3) Uani 1 1 d . . . H8A H 0.2602 0.3806 -0.0314 0.041(11) Uiso 1 1 calc R . . H8B H 0.2894 0.4890 -0.0448 0.041(11) Uiso 1 1 calc R . . H8C H 0.1609 0.4584 -0.0482 0.041(11) Uiso 1 1 calc R . . C9 C 0.2244(8) 0.5665(6) 0.0596(5) 0.043(2) Uani 1 1 d . . . H9A H 0.2666 0.6110 0.0373 0.041(11) Uiso 1 1 calc R . . H9B H 0.2419 0.5792 0.1089 0.041(11) Uiso 1 1 calc R . . H9C H 0.1427 0.5747 0.0405 0.041(11) 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 0.02639(17) 0.02657(16) 0.02600(18) -0.00137(16) 0.00663(13) -0.00005(17) Se1 0.0347(5) 0.0334(4) 0.0316(5) -0.0047(4) 0.0119(4) -0.0102(4) Se2 0.0289(5) 0.0263(4) 0.0554(7) -0.0098(4) -0.0028(5) 0.0039(4) P1 0.0241(11) 0.0223(9) 0.0245(12) 0.0000(9) 0.0088(10) 0.0004(9) P2 0.0229(11) 0.0241(11) 0.0289(13) -0.0012(10) 0.0061(11) 0.0006(9) Cl1 0.0562(16) 0.0469(13) 0.0342(13) -0.0093(11) 0.0213(13) -0.0054(13) N2 0.024(4) 0.020(3) 0.027(4) 0.002(3) 0.008(3) 0.001(3) N1 0.028(4) 0.041(4) 0.028(4) 0.007(3) 0.002(4) 0.013(3) C1 0.019(4) 0.040(5) 0.020(5) 0.005(4) 0.004(4) -0.006(4) C2 0.034(5) 0.033(5) 0.029(5) -0.007(4) 0.006(5) -0.008(4) C3 0.034(5) 0.043(5) 0.034(6) -0.004(4) 0.012(5) -0.002(5) C4 0.050(6) 0.035(5) 0.038(6) 0.001(4) 0.017(5) -0.012(5) C5 0.058(7) 0.024(4) 0.040(6) 0.000(4) 0.016(5) -0.001(5) C6 0.035(5) 0.032(5) 0.031(5) -0.005(4) 0.005(5) 0.001(4) C10 0.029(5) 0.025(4) 0.022(5) -0.005(4) 0.005(4) 0.002(4) C11 0.033(5) 0.035(5) 0.028(5) -0.004(4) 0.012(4) 0.000(4) C12 0.051(7) 0.043(6) 0.046(7) 0.020(5) -0.007(6) 0.004(5) C13 0.055(7) 0.029(5) 0.051(7) 0.001(5) -0.024(6) 0.011(5) C14 0.036(6) 0.042(6) 0.060(7) -0.012(5) 0.010(6) 0.014(5) C15 0.034(5) 0.050(6) 0.042(6) -0.002(5) 0.020(5) 0.003(5) C16 0.020(4) 0.026(4) 0.030(5) 0.000(4) 0.005(4) 0.004(4) C17 0.046(6) 0.046(5) 0.022(5) -0.005(4) 0.002(5) -0.007(5) C18 0.058(7) 0.042(6) 0.047(7) -0.006(5) 0.008(6) -0.006(5) C19 0.048(7) 0.075(8) 0.035(6) -0.009(6) 0.007(6) -0.005(6) C20 0.032(5) 0.061(6) 0.035(6) 0.009(5) 0.008(5) 0.002(5) C21 0.022(5) 0.052(6) 0.026(5) -0.004(5) 0.005(4) 0.009(4) C22 0.018(4) 0.040(5) 0.031(5) 0.013(4) 0.005(4) 0.004(4) C23 0.030(5) 0.049(5) 0.026(5) 0.001(5) 0.004(4) -0.011(5) C24 0.039(6) 0.077(8) 0.037(6) 0.005(6) 0.001(5) -0.005(6) C25 0.035(6) 0.092(9) 0.033(6) 0.002(7) 0.002(5) 0.010(6) C26 0.056(8) 0.073(8) 0.056(8) 0.033(7) 0.028(7) 0.019(7) C27 0.055(7) 0.036(5) 0.057(8) 0.004(5) 0.026(6) 0.007(5) C28 0.022(4) 0.033(4) 0.025(5) -0.017(4) 0.006(4) -0.002(4) C29 0.029(5) 0.031(5) 0.055(7) 0.003(5) 0.014(5) -0.003(4) C30 0.049(7) 0.040(6) 0.070(8) -0.002(5) 0.027(6) -0.016(5) C31 0.033(6) 0.069(7) 0.047(7) -0.016(6) 0.020(5) -0.014(6) C32 0.030(5) 0.076(8) 0.041(6) -0.013(6) 0.016(5) 0.010(5) C33 0.037(6) 0.036(5) 0.036(6) -0.001(4) 0.012(5) 0.004(5) C7 0.032(5) 0.042(5) 0.038(6) 0.000(5) 0.002(5) 0.010(5) C8 0.035(5) 0.072(7) 0.024(5) 0.006(5) -0.005(5) 0.006(6) C9 0.040(6) 0.046(5) 0.040(6) 0.020(5) 0.004(5) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.266(8) . y Bi1 N1 2.575(7) . y Bi1 Cl1 2.647(2) . y Bi1 Se2 2.8905(12) . y Bi1 Se1 3.0184(14) . y Se1 P1 2.159(2) . y Se2 P2 2.176(2) . y P1 N2 1.605(7) . y P1 C10 1.799(8) . y P1 C16 1.813(9) . y P2 N2 1.578(6) . y P2 C28 1.798(8) . y P2 C22 1.811(9) . y N1 C8 1.455(11) . y N1 C7 1.478(11) . y N1 C9 1.485(10) . y C1 C6 1.370(11) . y C1 C2 1.385(11) . y C2 C3 1.398(11) . y C2 C7 1.489(11) . y C3 C4 1.355(12) . y C4 C5 1.373(13) . y C5 C6 1.373(12) . y C10 C11 1.381(11) . y C10 C15 1.388(11) . y C11 C12 1.384(12) . y C12 C13 1.345(14) . y C13 C14 1.386(14) . y C14 C15 1.387(13) . y C16 C17 1.375(11) . y C16 C21 1.387(12) . y C17 C18 1.360(13) . y C18 C19 1.390(14) . y C19 C20 1.402(13) . y C20 C21 1.368(12) . y C22 C27 1.382(12) . y C22 C23 1.408(12) . y C23 C24 1.366(13) . y C24 C25 1.364(14) . y C25 C26 1.360(15) . y C26 C27 1.384(15) . y C28 C29 1.391(11) . y C28 C33 1.392(11) . y C29 C30 1.395(12) . y C30 C31 1.325(13) . y C31 C32 1.389(14) . y C32 C33 1.359(13) . y 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 72.9(3) . . y C1 Bi1 Cl1 85.5(2) . . y N1 Bi1 Cl1 95.10(18) . . y C1 Bi1 Se2 92.7(2) . . y N1 Bi1 Se2 164.81(16) . . y Cl1 Bi1 Se2 88.54(7) . . y C1 Bi1 Se1 81.4(2) . . y N1 Bi1 Se1 86.75(17) . . y Cl1 Bi1 Se1 165.65(6) . . y Se2 Bi1 Se1 86.18(4) . . y P1 Se1 Bi1 87.16(7) . . y P2 Se2 Bi1 92.59(7) . . y N2 P1 C10 105.8(4) . . y N2 P1 C16 110.5(4) . . y C10 P1 C16 104.5(4) . . y N2 P1 Se1 116.2(2) . . y C10 P1 Se1 109.7(3) . . y C16 P1 Se1 109.5(3) . . y N2 P2 C28 106.4(4) . . y N2 P2 C22 111.8(4) . . y C28 P2 C22 104.0(4) . . y N2 P2 Se2 116.6(3) . . y C28 P2 Se2 108.5(3) . . y C22 P2 Se2 108.7(3) . . y P2 N2 P1 130.7(4) . . y C8 N1 C7 111.8(7) . . y C8 N1 C9 111.5(7) . . y C7 N1 C9 110.0(7) . . y C8 N1 Bi1 109.4(5) . . y C7 N1 Bi1 104.1(5) . . y C9 N1 Bi1 109.8(5) . . y C6 C1 C2 121.3(8) . . y C6 C1 Bi1 122.9(6) . . y C2 C1 Bi1 115.7(6) . . y C1 C2 C3 117.3(8) . . y C1 C2 C7 122.1(8) . . y C3 C2 C7 120.4(8) . . y C4 C3 C2 120.9(9) . . y C3 C4 C5 121.3(9) . . y C4 C5 C6 118.8(9) . . y C1 C6 C5 120.5(9) . . y C11 C10 C15 119.8(8) . . y C11 C10 P1 121.2(7) . . y C15 C10 P1 118.9(7) . . y C10 C11 C12 118.9(9) . . y C13 C12 C11 121.6(10) . . y C12 C13 C14 120.5(9) . . y C13 C14 C15 119.0(9) . . y C14 C15 C10 120.2(9) . . y C17 C16 C21 118.3(8) . . y C17 C16 P1 118.1(7) . . y C21 C16 P1 123.5(7) . . y C18 C17 C16 122.3(9) . . y C17 C18 C19 119.1(10) . . y C18 C19 C20 120.0(10) . . y C21 C20 C19 119.0(10) . . y C20 C21 C16 121.4(9) . . y C27 C22 C23 119.4(9) . . y C27 C22 P2 124.7(8) . . y C23 C22 P2 115.8(6) . . y C24 C23 C22 120.5(9) . . y C25 C24 C23 119.1(10) . . y C26 C25 C24 121.6(10) . . y C25 C26 C27 120.7(10) . . y C22 C27 C26 118.8(10) . . y C29 C28 C33 118.6(8) . . y C29 C28 P2 120.3(6) . . y C33 C28 P2 120.9(7) . . y C28 C29 C30 119.6(9) . . y C31 C30 C29 121.1(9) . . y C30 C31 C32 119.9(10) . . y C33 C32 C31 120.8(9) . . y C32 C33 C28 120.0(9) . . y N1 C7 C2 111.5(7) . . y 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 C1 Bi1 Se1 P1 168.0(2) . . . . y N1 Bi1 Se1 P1 -118.78(17) . . . . y Cl1 Bi1 Se1 P1 143.3(2) . . . . y Se2 Bi1 Se1 P1 74.68(7) . . . . y C1 Bi1 Se2 P2 -143.0(2) . . . . y N1 Bi1 Se2 P2 -124.2(6) . . . . y Cl1 Bi1 Se2 P2 131.56(9) . . . . y Se1 Bi1 Se2 P2 -61.79(7) . . . . y Bi1 Se1 P1 N2 -34.0(3) . . . . y Bi1 Se1 P1 C10 85.8(3) . . . . y Bi1 Se1 P1 C16 -160.0(3) . . . . y Bi1 Se2 P2 N2 8.7(3) . . . . y Bi1 Se2 P2 C28 -111.4(3) . . . . y Bi1 Se2 P2 C22 136.1(3) . . . . y C28 P2 N2 P1 -162.7(5) . . . . y C22 P2 N2 P1 -49.7(7) . . . . y Se2 P2 N2 P1 76.1(6) . . . . y C10 P1 N2 P2 -176.9(5) . . . . y C16 P1 N2 P2 70.6(6) . . . . y Se1 P1 N2 P2 -54.9(6) . . . . y C1 Bi1 N1 C8 -93.3(6) . . . . y Cl1 Bi1 N1 C8 -9.6(6) . . . . y Se2 Bi1 N1 C8 -113.0(7) . . . . y Se1 Bi1 N1 C8 -175.3(6) . . . . y C1 Bi1 N1 C7 26.3(5) . . . . y Cl1 Bi1 N1 C7 110.0(5) . . . . y Se2 Bi1 N1 C7 6.6(10) . . . . y Se1 Bi1 N1 C7 -55.7(5) . . . . y C1 Bi1 N1 C9 144.1(6) . . . . y Cl1 Bi1 N1 C9 -132.2(5) . . . . y Se2 Bi1 N1 C9 124.4(6) . . . . y Se1 Bi1 N1 C9 62.0(5) . . . . y N1 Bi1 C1 C6 166.3(8) . . . . y Cl1 Bi1 C1 C6 69.6(7) . . . . y Se2 Bi1 C1 C6 -18.7(7) . . . . y Se1 Bi1 C1 C6 -104.4(7) . . . . y N1 Bi1 C1 C2 -9.8(6) . . . . y Cl1 Bi1 C1 C2 -106.5(6) . . . . y Se2 Bi1 C1 C2 165.1(6) . . . . y Se1 Bi1 C1 C2 79.4(6) . . . . y C6 C1 C2 C3 -0.7(13) . . . . y Bi1 C1 C2 C3 175.5(6) . . . . y C6 C1 C2 C7 174.1(8) . . . . y Bi1 C1 C2 C7 -9.7(11) . . . . y C1 C2 C3 C4 1.7(13) . . . . y C7 C2 C3 C4 -173.2(9) . . . . y C2 C3 C4 C5 -2.2(14) . . . . y C3 C4 C5 C6 1.5(14) . . . . y C2 C1 C6 C5 0.1(14) . . . . y Bi1 C1 C6 C5 -175.8(7) . . . . y C4 C5 C6 C1 -0.5(14) . . . . y N2 P1 C10 C11 1.3(8) . . . . y C16 P1 C10 C11 118.0(7) . . . . y Se1 P1 C10 C11 -124.8(7) . . . . y N2 P1 C10 C15 -178.6(7) . . . . y C16 P1 C10 C15 -61.9(8) . . . . y Se1 P1 C10 C15 55.4(7) . . . . y C15 C10 C11 C12 -0.2(13) . . . . y P1 C10 C11 C12 179.9(7) . . . . y C10 C11 C12 C13 1.1(14) . . . . y C11 C12 C13 C14 -1.1(16) . . . . y C12 C13 C14 C15 0.2(15) . . . . y C13 C14 C15 C10 0.6(14) . . . . y C11 C10 C15 C14 -0.6(13) . . . . y P1 C10 C15 C14 179.2(7) . . . . y N2 P1 C16 C17 69.3(8) . . . . y C10 P1 C16 C17 -44.1(8) . . . . y Se1 P1 C16 C17 -161.6(6) . . . . y N2 P1 C16 C21 -105.2(7) . . . . y C10 P1 C16 C21 141.4(7) . . . . y Se1 P1 C16 C21 24.0(8) . . . . y C21 C16 C17 C18 -0.4(14) . . . . y P1 C16 C17 C18 -175.2(8) . . . . y C16 C17 C18 C19 0.4(16) . . . . ? C17 C18 C19 C20 0.6(16) . . . . ? C18 C19 C20 C21 -1.6(15) . . . . ? C19 C20 C21 C16 1.6(14) . . . . ? C17 C16 C21 C20 -0.6(13) . . . . ? P1 C16 C21 C20 173.9(7) . . . . ? N2 P2 C22 C27 118.1(8) . . . . ? C28 P2 C22 C27 -127.4(8) . . . . ? Se2 P2 C22 C27 -11.9(9) . . . . ? N2 P2 C22 C23 -58.5(7) . . . . ? C28 P2 C22 C23 56.0(7) . . . . ? Se2 P2 C22 C23 171.5(6) . . . . ? C27 C22 C23 C24 0.7(14) . . . . ? P2 C22 C23 C24 177.5(7) . . . . ? C22 C23 C24 C25 -0.1(15) . . . . ? C23 C24 C25 C26 0.3(17) . . . . ? C24 C25 C26 C27 -1.2(17) . . . . ? C23 C22 C27 C26 -1.5(14) . . . . ? P2 C22 C27 C26 -178.0(8) . . . . ? C25 C26 C27 C22 1.7(16) . . . . ? N2 P2 C28 C29 8.2(8) . . . . ? C22 P2 C28 C29 -110.0(7) . . . . ? Se2 P2 C28 C29 134.5(7) . . . . ? N2 P2 C28 C33 -177.2(7) . . . . ? C22 P2 C28 C33 64.6(8) . . . . ? Se2 P2 C28 C33 -51.0(7) . . . . ? C33 C28 C29 C30 2.2(14) . . . . ? P2 C28 C29 C30 176.9(8) . . . . ? C28 C29 C30 C31 -2.0(16) . . . . ? C29 C30 C31 C32 1.0(16) . . . . ? C30 C31 C32 C33 -0.3(16) . . . . ? C31 C32 C33 C28 0.7(15) . . . . ? C29 C28 C33 C32 -1.6(13) . . . . ? P2 C28 C33 C32 -176.3(7) . . . . ? C8 N1 C7 C2 79.4(9) . . . . ? C9 N1 C7 C2 -156.2(7) . . . . ? Bi1 N1 C7 C2 -38.6(8) . . . . ? C1 C2 C7 N1 36.6(12) . . . . ? C3 C2 C7 N1 -148.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.982 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.179