Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Zvesti #============================================================================ _journal_coden_Cambridge 0022 # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Hans Joachim Breunig Institut fur Anorganische und Physikalische Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; _publ_contact_author_phone '049 421 2182266' _publ_contact_author_fax '049 421 2184267' _publ_contact_author_email breunig@chemie.uni-bremen.de _publ_requested_coeditor_name ? _publ_section_title ; Hypervalent organobismuth(III)carbonate, chalcogenides and halides with the pendant arm ligands 2-(Me2NCH2)C6H4 and 2,6-(Me2NCH2)2C6H3. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address H.J.Breunig ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; L.Konigsmann ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; E.Lork ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; N.Philipp ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; M.Nema ; Facultatea de Chimie si Inginieri Chimica Universitatea Babes-Bolyai RO-400028 Cluj-Napoca Romania ; C.Silvestru ; Facultatea de Chimie si Inginieri Chimica Universitatea Babes-Bolyai RO-400028 Cluj-Napoca Romania ; ; A.Soran ; ; Facultatea de Chimie si Inginieri Chimica Universitatea Babes-Bolyai RO-400028 Cluj-Napoca Romania ; R.Varga ; Facultatea de Chimie si Inginieri Chimica Universitatea Babes-Bolyai RO-400028 Cluj-Napoca Romania ; R.Wagner ; Institut fur Anorganische und Physikalisch Chemie der Universitat Postfach 330 440 28334 Bremen Bundesrepublik Deutschland ; _publ_contact_author_name 'Hans Joachim Breunig' # Attachment 'Compound 9 - CCDC 652892.cif' data_84richy _database_code_depnum_ccdc_archive 'CCDC 652892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H38 Bi2 N4 S2' _chemical_formula_sum 'C24 H38 Bi2 N4 S2' _chemical_formula_weight 864.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.435(2) _cell_length_b 11.581(4) _cell_length_c 19.000(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.094(5) _cell_angle_gamma 90.00 _cell_volume 1398.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4148 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.10 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 12.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.043 _exptl_absorpt_correction_T_max 0.070 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 10948 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2847 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0140P)^2^+3.0962P] 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 2847 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0596 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 0.27625(3) 0.556790(16) 0.044642(10) 0.02997(8) Uani 1 1 d . . . N1 N 0.3310(7) 0.5526(4) 0.1956(3) 0.0368(11) Uani 1 1 d . . . N2 N 0.0599(7) 0.7557(4) -0.0177(2) 0.0335(10) Uani 1 1 d . . . S1 S 0.6035(3) 0.42800(13) 0.07819(8) 0.0448(4) Uani 1 1 d . . . C1 C 0.4127(8) 0.7231(5) 0.0943(3) 0.0306(12) Uani 1 1 d . . . C2 C 0.5174(8) 0.7229(5) 0.1641(3) 0.0371(13) Uani 1 1 d . . . C3 C 0.6066(9) 0.8247(6) 0.1937(3) 0.0498(16) Uani 1 1 d . . . H3 H 0.6802 0.8251 0.2400 0.060 Uiso 1 1 calc R . . C4 C 0.5853(11) 0.9257(6) 0.1541(4) 0.0507(17) Uani 1 1 d . . . H4 H 0.6538 0.9925 0.1724 0.061 Uiso 1 1 calc R . . C5 C 0.4648(10) 0.9275(5) 0.0885(4) 0.0479(16) Uani 1 1 d . . . H5 H 0.4395 0.9972 0.0644 0.057 Uiso 1 1 calc R . . C6 C 0.3787(8) 0.8258(5) 0.0572(3) 0.0338(12) Uani 1 1 d . . . C7 C 0.5261(9) 0.6162(5) 0.2090(3) 0.0400(14) Uani 1 1 d . . . H7A H 0.6400 0.5672 0.1989 0.048 Uiso 1 1 calc R . . H7B H 0.5551 0.6376 0.2590 0.048 Uiso 1 1 calc R . . C8 C 0.3504(11) 0.4407(5) 0.2308(4) 0.0520(17) Uani 1 1 d . . . H8A H 0.4567 0.3960 0.2131 0.078 Uiso 1 1 calc R . . H8B H 0.2182 0.4008 0.2212 0.078 Uiso 1 1 calc R . . H8C H 0.3890 0.4514 0.2813 0.078 Uiso 1 1 calc R . . C9 C 0.1526(10) 0.6182(6) 0.2164(3) 0.0510(16) Uani 1 1 d . . . H9A H 0.1801 0.6338 0.2666 0.076 Uiso 1 1 calc R . . H9B H 0.0260 0.5735 0.2055 0.076 Uiso 1 1 calc R . . H9C H 0.1361 0.6897 0.1906 0.076 Uiso 1 1 calc R . . C10 C 0.2426(9) 0.8308(5) -0.0140(3) 0.0368(12) Uani 1 1 d . . . H10A H 0.1958 0.9097 -0.0236 0.044 Uiso 1 1 calc R . . H10B H 0.3245 0.8082 -0.0504 0.044 Uiso 1 1 calc R . . C11 C -0.0829(9) 0.7929(6) 0.0301(4) 0.0523(17) Uani 1 1 d . . . H11A H -0.0073 0.7987 0.0777 0.078 Uiso 1 1 calc R . . H11B H -0.1945 0.7376 0.0290 0.078 Uiso 1 1 calc R . . H11C H -0.1411 0.8668 0.0150 0.078 Uiso 1 1 calc R . . C12 C -0.0522(10) 0.7503(6) -0.0904(3) 0.0512(17) Uani 1 1 d . . . H12A H -0.1690 0.6982 -0.0925 0.077 Uiso 1 1 calc R . . H12B H 0.0413 0.7233 -0.1215 0.077 Uiso 1 1 calc R . . H12C H -0.1029 0.8258 -0.1052 0.077 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 0.03278(12) 0.02503(12) 0.03122(12) -0.00296(9) 0.00236(8) -0.00149(9) N1 0.036(3) 0.038(3) 0.038(3) 0.006(2) 0.010(2) -0.002(2) N2 0.035(2) 0.026(2) 0.039(3) 0.003(2) 0.006(2) 0.0038(19) S1 0.0585(10) 0.0464(9) 0.0295(8) 0.0019(6) 0.0067(7) 0.0229(7) C1 0.028(3) 0.031(3) 0.034(3) -0.009(2) 0.009(2) -0.003(2) C2 0.026(3) 0.051(4) 0.035(3) -0.012(3) 0.009(2) -0.007(2) C3 0.040(3) 0.064(4) 0.046(4) -0.024(3) 0.009(3) -0.015(3) C4 0.055(4) 0.044(4) 0.056(4) -0.026(3) 0.020(3) -0.022(3) C5 0.051(4) 0.036(4) 0.062(5) -0.007(3) 0.024(3) -0.011(3) C6 0.039(3) 0.027(3) 0.040(3) -0.006(2) 0.018(2) 0.000(2) C7 0.037(3) 0.054(4) 0.028(3) -0.005(3) 0.001(2) -0.001(3) C8 0.061(4) 0.053(4) 0.043(4) 0.013(3) 0.009(3) 0.000(3) C9 0.046(4) 0.065(5) 0.045(4) -0.002(3) 0.019(3) 0.004(3) C10 0.042(3) 0.026(3) 0.044(3) 0.002(3) 0.013(2) -0.002(2) C11 0.035(3) 0.057(4) 0.067(4) 0.006(4) 0.017(3) 0.011(3) C12 0.056(4) 0.047(4) 0.045(4) 0.011(3) -0.008(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.260(5) . ? Bi1 S1 2.5770(16) . ? Bi1 S1 2.5784(17) 3_665 ? N1 C7 1.443(7) . ? N1 C8 1.455(7) . ? N1 C9 1.481(7) . ? N2 C12 1.455(7) . ? N2 C11 1.455(7) . ? N2 C10 1.455(7) . ? S1 Bi1 2.5784(17) 3_665 ? C1 C6 1.383(8) . ? C1 C2 1.389(7) . ? C2 C3 1.391(8) . ? C2 C7 1.498(8) . ? C3 C4 1.386(9) . ? C4 C5 1.359(10) . ? C5 C6 1.394(8) . ? C6 C10 1.492(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 S1 98.13(14) . . ? C1 Bi1 S1 99.65(14) . 3_665 ? S1 Bi1 S1 85.01(5) . 3_665 ? C7 N1 C8 111.4(5) . . ? C7 N1 C9 112.4(5) . . ? C8 N1 C9 110.3(5) . . ? C12 N2 C11 109.7(5) . . ? C12 N2 C10 110.4(5) . . ? C11 N2 C10 112.2(5) . . ? Bi1 S1 Bi1 94.99(5) . 3_665 ? C6 C1 C2 120.1(5) . . ? C6 C1 Bi1 120.0(4) . . ? C2 C1 Bi1 119.7(4) . . ? C1 C2 C3 119.5(6) . . ? C1 C2 C7 120.9(5) . . ? C3 C2 C7 119.6(5) . . ? C4 C3 C2 119.8(6) . . ? C5 C4 C3 120.3(6) . . ? C4 C5 C6 120.6(6) . . ? C1 C6 C5 119.3(5) . . ? C1 C6 C10 121.2(5) . . ? C5 C6 C10 119.4(5) . . ? N1 C7 C2 111.6(5) . . ? N2 C10 C6 112.0(4) . . ? 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 Bi1 -99.06(14) . . . 3_665 ? S1 Bi1 S1 Bi1 0.0 3_665 . . 3_665 ? S1 Bi1 C1 C6 135.4(4) . . . . ? S1 Bi1 C1 C6 49.1(4) 3_665 . . . ? S1 Bi1 C1 C2 -49.2(4) . . . . ? S1 Bi1 C1 C2 -135.5(4) 3_665 . . . ? C6 C1 C2 C3 -6.6(8) . . . . ? Bi1 C1 C2 C3 178.1(4) . . . . ? C6 C1 C2 C7 170.2(5) . . . . ? Bi1 C1 C2 C7 -5.1(7) . . . . ? C1 C2 C3 C4 1.7(8) . . . . ? C7 C2 C3 C4 -175.2(6) . . . . ? C2 C3 C4 C5 4.9(9) . . . . ? C3 C4 C5 C6 -6.6(10) . . . . ? C2 C1 C6 C5 4.9(8) . . . . ? Bi1 C1 C6 C5 -179.7(4) . . . . ? C2 C1 C6 C10 -171.8(5) . . . . ? Bi1 C1 C6 C10 3.6(6) . . . . ? C4 C5 C6 C1 1.7(8) . . . . ? C4 C5 C6 C10 178.5(5) . . . . ? C8 N1 C7 C2 171.2(5) . . . . ? C9 N1 C7 C2 -64.4(6) . . . . ? C1 C2 C7 N1 -37.4(7) . . . . ? C3 C2 C7 N1 139.4(5) . . . . ? C12 N2 C10 C6 -171.9(5) . . . . ? C11 N2 C10 C6 65.4(6) . . . . ? C1 C6 C10 N2 38.2(7) . . . . ? C5 C6 C10 N2 -138.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.578 _refine_diff_density_min -1.031 _refine_diff_density_rms 0.127 # Attachment 'Compound 8-0.5C6H6 - CCDC 652893.cif' data_353rich _database_code_depnum_ccdc_archive 'CCDC 652893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Bi2 N2 O10 S2 W2, 0.5(C6)' _chemical_formula_sum 'C31 H24 Bi2 N2 O10 S2 W2' _chemical_formula_weight 1434.30 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.8825(10) _cell_length_b 12.0273(11) _cell_length_c 16.1174(14) _cell_angle_alpha 99.254(2) _cell_angle_beta 96.479(2) _cell_angle_gamma 115.567(2) _cell_volume 2007.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4232 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 22.48 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1300 _exptl_absorpt_coefficient_mu 14.606 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.044 _exptl_absorpt_correction_T_max 0.073 _exptl_absorpt_process_details 'Bruker, 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 21482 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 26.37 _reflns_number_total 8136 _reflns_number_gt 6359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8136 _refine_ls_number_parameters 446 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 W2 W 1.08195(5) 0.62759(5) 0.80481(3) 0.04984(16) Uani 1 1 d . . . Bi1 Bi 0.75552(4) 0.28659(4) 0.80852(3) 0.04334(14) Uani 1 1 d . . . Bi2 Bi 0.89682(4) 0.25047(4) 0.61433(3) 0.03932(13) Uani 1 1 d . . . C1 C 0.7888(12) 0.1320(11) 0.8528(8) 0.050(3) Uani 1 1 d . . . C2 C 0.6788(15) 0.0272(13) 0.8567(9) 0.066(4) Uani 1 1 d . . . C3 C 0.6870(17) -0.0734(14) 0.8846(9) 0.079(5) Uani 1 1 d . . . H3 H 0.6145 -0.1452 0.8868 0.094 Uiso 1 1 calc R . . C4 C 0.807(2) -0.0615(16) 0.9086(11) 0.084(5) Uani 1 1 d . . . H4 H 0.8144 -0.1282 0.9264 0.101 Uiso 1 1 calc R . . C5 C 0.9152(17) 0.0426(17) 0.9075(10) 0.081(5) Uani 1 1 d . . . H5 H 0.9945 0.0478 0.9266 0.098 Uiso 1 1 calc R . . C6 C 0.9064(15) 0.1414(13) 0.8777(9) 0.066(4) Uani 1 1 d . . . H6 H 0.9793 0.2123 0.8748 0.080 Uiso 1 1 calc R . . C7 C 0.5495(14) 0.0150(14) 0.8270(10) 0.072(4) Uani 1 1 d . . . H7A H 0.5230 -0.0203 0.7655 0.087 Uiso 1 1 calc R . . H7B H 0.4892 -0.0433 0.8546 0.087 Uiso 1 1 calc R . . C8 C 0.5588(16) 0.1753(16) 0.9395(10) 0.093(6) Uani 1 1 d . . . H8A H 0.4808 0.1229 0.9552 0.140 Uiso 1 1 calc R . . H8B H 0.5763 0.2624 0.9554 0.140 Uiso 1 1 calc R . . H8C H 0.6274 0.1650 0.9689 0.140 Uiso 1 1 calc R . . C9 C 0.4334(14) 0.1336(17) 0.7973(11) 0.092(6) Uani 1 1 d . . . H9A H 0.4335 0.1151 0.7371 0.137 Uiso 1 1 calc R . . H9B H 0.4338 0.2142 0.8134 0.137 Uiso 1 1 calc R . . H9C H 0.3585 0.0688 0.8090 0.137 Uiso 1 1 calc R . . C10 C 0.9185(11) 0.0877(11) 0.6529(8) 0.043(3) Uani 1 1 d . . . C11 C 1.0406(11) 0.1030(12) 0.6713(8) 0.049(3) Uani 1 1 d . . . C12 C 1.0576(16) 0.0023(16) 0.6961(10) 0.076(5) Uani 1 1 d . . . H12 H 1.1394 0.0096 0.7067 0.091 Uiso 1 1 calc R . . C13 C 0.9587(15) -0.1038(14) 0.7047(10) 0.071(5) Uani 1 1 d . . . H13 H 0.9725 -0.1672 0.7230 0.085 Uiso 1 1 calc R . . C14 C 0.8408(15) -0.1161(12) 0.6865(9) 0.063(4) Uani 1 1 d . . . H14 H 0.7726 -0.1903 0.6907 0.076 Uiso 1 1 calc R . . C15 C 0.8168(11) -0.0216(11) 0.6616(8) 0.050(3) Uani 1 1 d . . . H15 H 0.7341 -0.0314 0.6510 0.060 Uiso 1 1 calc R . . C16 C 1.1543(11) 0.2253(13) 0.6696(8) 0.054(3) Uani 1 1 d . . . H16A H 1.1826 0.2832 0.7256 0.064 Uiso 1 1 calc R . . H16B H 1.2238 0.2076 0.6573 0.064 Uiso 1 1 calc R . . C17 C 1.2145(12) 0.4184(12) 0.6171(10) 0.067(4) Uani 1 1 d . . . H17A H 1.2983 0.4254 0.6180 0.100 Uiso 1 1 calc R . . H17B H 1.2134 0.4659 0.6706 0.100 Uiso 1 1 calc R . . H17C H 1.1924 0.4514 0.5709 0.100 Uiso 1 1 calc R . . C18 C 1.1056(13) 0.2139(14) 0.5161(9) 0.068(4) Uani 1 1 d . . . H18A H 1.0848 0.2558 0.4755 0.103 Uiso 1 1 calc R . . H18B H 1.0379 0.1293 0.5067 0.103 Uiso 1 1 calc R . . H18C H 1.1833 0.2106 0.5089 0.103 Uiso 1 1 calc R . . C19 C 0.4662(11) 0.3326(12) 0.4851(8) 0.050(3) Uani 1 1 d . . . C20 C 0.3885(12) 0.1070(13) 0.5484(8) 0.049(3) Uani 1 1 d . . . C21 C 0.5976(12) 0.1967(13) 0.4542(8) 0.055(3) Uani 1 1 d . . . C22 C 0.7183(13) 0.4332(14) 0.5811(9) 0.059(4) Uani 1 1 d . . . C23 C 0.5181(13) 0.3584(14) 0.6654(10) 0.060(4) Uani 1 1 d . . . C30 C 0.559(6) 0.548(5) 0.942(4) 0.23(2) Uani 1 1 d DU . . C31 C 0.430(7) 0.484(5) 0.926(2) 0.25(2) Uani 1 1 d DU . . C32 C 0.364(4) 0.432(4) 0.984(6) 0.34(3) Uani 1 1 d DU . . N1 N 0.5469(10) 0.1380(11) 0.8466(7) 0.061(3) Uani 1 1 d . . . N2 N 1.1222(9) 0.2849(10) 0.6045(7) 0.054(3) Uani 1 1 d . . . O1 O 0.4206(10) 0.3680(10) 0.4388(7) 0.090(4) Uani 1 1 d . . . O2 O 0.2944(8) 0.0219(9) 0.5411(6) 0.070(3) Uani 1 1 d . . . O3 O 0.6176(10) 0.1619(11) 0.3902(7) 0.090(4) Uani 1 1 d . . . O4 O 0.8035(9) 0.5261(11) 0.5896(8) 0.094(4) Uani 1 1 d . . . O5 O 0.4955(11) 0.4153(12) 0.7195(8) 0.098(4) Uani 1 1 d . . . S1 S 0.6600(3) 0.1650(3) 0.65267(19) 0.0399(7) Uani 1 1 d . . . S2 S 0.9925(3) 0.3842(3) 0.7682(2) 0.0425(7) Uani 1 1 d . . . W1 W 0.55624(4) 0.26945(4) 0.56329(3) 0.03995(14) Uani 1 1 d . . . O6 O 0.8132(13) 0.6240(12) 0.7986(11) 0.125(5) Uani 1 1 d . . . O7 O 1.1962(12) 0.9179(10) 0.8779(8) 0.108(4) Uani 1 1 d . . . O8 O 1.0890(11) 0.6591(14) 0.6140(8) 0.110(5) Uani 1 1 d . . . O9 O 1.3662(10) 0.6745(12) 0.8188(10) 0.123(5) Uani 1 1 d . . . O10 O 1.1151(16) 0.6038(15) 0.9969(8) 0.175(8) Uani 1 1 d . . . C24 C 0.9077(15) 0.6208(12) 0.8014(11) 0.068(4) Uani 1 1 d . . . C25 C 1.1543(15) 0.8115(13) 0.8502(10) 0.074(5) Uani 1 1 d . . . C26 C 1.0832(12) 0.6470(13) 0.6835(12) 0.066(4) Uani 1 1 d . . . C27 C 1.2641(15) 0.6520(14) 0.8130(11) 0.080(5) Uani 1 1 d . . . C28 C 1.0944(17) 0.6115(13) 0.9258(11) 0.098(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 W2 0.0506(3) 0.0345(3) 0.0497(3) 0.0077(2) 0.0021(2) 0.0090(2) Bi1 0.0460(3) 0.0405(3) 0.0381(3) 0.0104(2) 0.0052(2) 0.0153(2) Bi2 0.0381(2) 0.0403(3) 0.0415(3) 0.0112(2) 0.00380(19) 0.0202(2) C1 0.052(8) 0.033(7) 0.047(8) 0.015(6) 0.006(6) 0.002(6) C2 0.094(12) 0.048(8) 0.042(8) 0.005(7) -0.002(8) 0.026(8) C3 0.100(13) 0.045(9) 0.057(10) 0.009(7) -0.007(9) 0.010(9) C4 0.115(15) 0.061(11) 0.084(13) 0.028(9) 0.017(11) 0.043(11) C5 0.093(13) 0.086(12) 0.068(11) 0.029(9) -0.007(9) 0.045(11) C6 0.084(11) 0.053(9) 0.051(9) 0.014(7) -0.004(8) 0.025(8) C7 0.063(10) 0.064(10) 0.068(11) 0.027(8) 0.002(8) 0.008(8) C8 0.113(14) 0.091(13) 0.059(11) 0.027(9) 0.036(10) 0.023(11) C9 0.055(10) 0.119(15) 0.094(13) 0.058(12) 0.022(9) 0.021(10) C10 0.044(7) 0.038(7) 0.050(8) 0.010(6) -0.004(6) 0.023(6) C11 0.034(7) 0.050(8) 0.060(9) 0.013(6) -0.006(6) 0.020(6) C12 0.082(11) 0.075(11) 0.091(12) 0.018(9) 0.002(9) 0.060(10) C13 0.074(10) 0.049(9) 0.088(12) 0.005(8) -0.018(9) 0.039(8) C14 0.084(11) 0.029(7) 0.068(10) 0.010(6) -0.003(8) 0.022(7) C15 0.035(7) 0.049(8) 0.054(8) 0.008(6) -0.001(6) 0.012(6) C16 0.049(8) 0.079(10) 0.056(9) 0.032(7) 0.018(6) 0.043(7) C17 0.046(8) 0.058(9) 0.095(12) 0.031(8) 0.032(8) 0.013(7) C18 0.069(10) 0.072(10) 0.060(10) 0.005(8) 0.021(8) 0.030(8) C19 0.034(7) 0.048(8) 0.054(9) 0.014(6) -0.003(6) 0.009(6) C20 0.038(7) 0.056(8) 0.049(8) 0.009(6) -0.007(6) 0.022(7) C21 0.049(8) 0.073(10) 0.035(8) 0.006(7) -0.008(6) 0.029(7) C22 0.048(8) 0.059(9) 0.068(10) 0.014(8) -0.007(7) 0.026(7) C23 0.052(8) 0.062(9) 0.059(10) 0.015(8) -0.004(7) 0.024(7) C30 0.30(5) 0.21(4) 0.22(4) -0.02(3) 0.00(3) 0.20(4) C31 0.45(7) 0.16(4) 0.19(4) 0.03(3) 0.01(4) 0.21(4) C32 0.51(7) 0.15(3) 0.37(7) 0.09(4) 0.03(7) 0.15(4) N1 0.056(7) 0.063(8) 0.059(8) 0.026(6) 0.020(6) 0.017(6) N2 0.043(6) 0.047(6) 0.072(8) 0.010(6) 0.018(6) 0.022(5) O1 0.094(8) 0.071(7) 0.094(9) 0.024(6) -0.038(6) 0.039(6) O2 0.040(5) 0.066(7) 0.082(7) 0.016(6) 0.006(5) 0.008(5) O3 0.087(8) 0.111(9) 0.059(7) -0.004(6) 0.024(6) 0.042(7) O4 0.047(6) 0.085(8) 0.115(10) 0.038(7) -0.009(6) 0.002(6) O5 0.097(9) 0.107(10) 0.089(9) -0.006(7) 0.021(7) 0.057(8) S1 0.0328(15) 0.0418(17) 0.0406(17) 0.0104(13) -0.0029(12) 0.0154(13) S2 0.0378(16) 0.0350(16) 0.0483(19) 0.0102(14) 0.0047(14) 0.0119(13) W1 0.0351(3) 0.0403(3) 0.0411(3) 0.0071(2) -0.0025(2) 0.0175(2) O6 0.103(10) 0.086(9) 0.215(17) 0.052(10) 0.072(11) 0.054(8) O7 0.134(11) 0.037(6) 0.115(10) 0.006(6) 0.027(8) 0.007(7) O8 0.095(9) 0.174(14) 0.078(9) 0.076(9) 0.025(7) 0.059(9) O9 0.042(7) 0.112(11) 0.195(15) 0.027(10) 0.000(8) 0.026(7) O10 0.190(16) 0.157(14) 0.049(9) 0.017(9) -0.026(9) -0.021(11) C24 0.071(10) 0.034(7) 0.104(13) 0.025(8) 0.037(9) 0.020(8) C25 0.090(11) 0.034(8) 0.074(11) 0.014(7) 0.017(9) 0.006(8) C26 0.037(7) 0.051(8) 0.111(14) 0.026(9) -0.006(8) 0.024(7) C27 0.056(10) 0.048(9) 0.101(13) 0.012(8) -0.006(9) 0.001(8) C28 0.123(15) 0.040(9) 0.048(10) -0.010(7) -0.012(10) -0.023(9) _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 W2 C25 1.966(14) . ? W2 C28 1.985(18) . ? W2 C26 2.006(18) . ? W2 C24 2.031(17) . ? W2 C27 2.041(18) . ? W2 S2 2.581(3) . ? Bi1 C1 2.263(13) . ? Bi1 S1 2.545(3) . ? Bi1 N1 2.568(10) . ? Bi1 S2 2.745(3) . ? Bi2 C10 2.253(11) . ? Bi2 N2 2.556(9) . ? Bi2 S2 2.556(3) . ? Bi2 S1 2.731(3) . ? C1 C6 1.360(18) . ? C1 C2 1.387(18) . ? C2 C3 1.393(19) . ? C2 C7 1.493(19) . ? C3 C4 1.37(2) . ? C3 H3 0.9300 . ? C4 C5 1.36(2) . ? C4 H4 0.9300 . ? C5 C6 1.390(19) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.476(17) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.464(17) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.462(17) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.372(15) . ? C10 C15 1.391(16) . ? C11 C12 1.419(17) . ? C11 C16 1.515(17) . ? C12 C13 1.35(2) . ? C12 H12 0.9300 . ? C13 C14 1.335(18) . ? C13 H13 0.9300 . ? C14 C15 1.392(17) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N2 1.467(14) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.465(15) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N2 1.482(15) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O1 1.115(13) . ? C19 W1 2.004(13) . ? C20 O2 1.120(14) . ? C20 W1 2.056(13) . ? C21 O3 1.139(14) . ? C21 W1 2.042(14) . ? C22 O4 1.111(15) . ? C22 W1 2.022(15) . ? C23 O5 1.150(16) . ? C23 W1 2.019(16) . ? C30 C32 1.34(5) 2_667 ? C30 C31 1.35(2) . ? C31 C32 1.35(2) . ? C32 C30 1.34(5) 2_667 ? S1 W1 2.587(3) . ? O6 C24 1.136(17) . ? O7 C25 1.140(15) . ? O8 C26 1.159(18) . ? O9 C27 1.112(17) . ? O10 C28 1.171(18) . ? 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 C25 W2 C28 87.3(6) . . ? C25 W2 C26 92.1(6) . . ? C28 W2 C26 175.7(7) . . ? C25 W2 C24 87.0(6) . . ? C28 W2 C24 91.2(8) . . ? C26 W2 C24 93.0(6) . . ? C25 W2 C27 87.7(6) . . ? C28 W2 C27 88.4(8) . . ? C26 W2 C27 87.4(6) . . ? C24 W2 C27 174.7(6) . . ? C25 W2 S2 171.6(5) . . ? C28 W2 S2 84.4(4) . . ? C26 W2 S2 96.1(4) . . ? C24 W2 S2 93.9(4) . . ? C27 W2 S2 91.3(4) . . ? C1 Bi1 S1 95.6(3) . . ? C1 Bi1 N1 73.4(4) . . ? S1 Bi1 N1 87.9(3) . . ? C1 Bi1 S2 90.0(3) . . ? S1 Bi1 S2 89.12(9) . . ? N1 Bi1 S2 162.8(3) . . ? C10 Bi2 N2 72.6(4) . . ? C10 Bi2 S2 90.6(3) . . ? N2 Bi2 S2 86.5(3) . . ? C10 Bi2 S1 91.1(3) . . ? N2 Bi2 S1 163.0(3) . . ? S2 Bi2 S1 89.22(9) . . ? C6 C1 C2 121.6(13) . . ? C6 C1 Bi1 123.7(9) . . ? C2 C1 Bi1 114.6(10) . . ? C1 C2 C3 120.0(15) . . ? C1 C2 C7 121.7(13) . . ? C3 C2 C7 118.2(14) . . ? C4 C3 C2 117.0(15) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? C5 C4 C3 123.4(16) . . ? C5 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C4 C5 C6 119.4(16) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 118.6(15) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 C2 112.2(11) . . ? N1 C7 H7A 109.2 . . ? C2 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C2 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 120.2(11) . . ? C11 C10 Bi2 116.2(9) . . ? C15 C10 Bi2 123.5(8) . . ? C10 C11 C12 117.7(12) . . ? C10 C11 C16 121.5(11) . . ? C12 C11 C16 120.7(11) . . ? C13 C12 C11 122.0(14) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C14 C13 C12 119.0(14) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 122.1(14) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C10 C15 C14 118.9(12) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N2 C16 C11 111.2(10) . . ? N2 C16 H16A 109.4 . . ? C11 C16 H16A 109.4 . . ? N2 C16 H16B 109.4 . . ? C11 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C19 W1 176.3(13) . . ? O2 C20 W1 176.7(12) . . ? O3 C21 W1 174.6(12) . . ? O4 C22 W1 176.3(12) . . ? O5 C23 W1 174.5(13) . . ? C32 C30 C31 125(4) 2_667 . ? C32 C31 C30 123(3) . . ? C30 C32 C31 112(4) 2_667 . ? C9 N1 C8 112.9(13) . . ? C9 N1 C7 112.1(12) . . ? C8 N1 C7 108.0(12) . . ? C9 N1 Bi1 113.5(8) . . ? C8 N1 Bi1 107.8(9) . . ? C7 N1 Bi1 101.8(8) . . ? C17 N2 C16 112.8(11) . . ? C17 N2 C18 110.5(11) . . ? C16 N2 C18 112.0(10) . . ? C17 N2 Bi2 113.7(7) . . ? C16 N2 Bi2 104.2(7) . . ? C18 N2 Bi2 103.2(7) . . ? Bi1 S1 W1 113.74(11) . . ? Bi1 S1 Bi2 91.01(8) . . ? W1 S1 Bi2 102.52(10) . . ? Bi2 S2 W2 122.17(12) . . ? Bi2 S2 Bi1 90.45(9) . . ? W2 S2 Bi1 106.70(11) . . ? C19 W1 C23 89.8(5) . . ? C19 W1 C22 89.6(5) . . ? C23 W1 C22 86.0(6) . . ? C19 W1 C21 85.0(5) . . ? C23 W1 C21 173.5(5) . . ? C22 W1 C21 90.1(6) . . ? C19 W1 C20 89.7(5) . . ? C23 W1 C20 91.8(5) . . ? C22 W1 C20 177.6(6) . . ? C21 W1 C20 92.1(5) . . ? C19 W1 S1 173.9(4) . . ? C23 W1 S1 94.6(4) . . ? C22 W1 S1 94.8(4) . . ? C21 W1 S1 90.9(4) . . ? C20 W1 S1 86.0(3) . . ? O6 C24 W2 176.0(13) . . ? O7 C25 W2 178.9(14) . . ? O8 C26 W2 177.2(12) . . ? O9 C27 W2 174.9(14) . . ? O10 C28 W2 173(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 S1 Bi1 C1 C6 111.4(11) . . . . ? N1 Bi1 C1 C6 -162.5(12) . . . . ? S2 Bi1 C1 C6 22.3(11) . . . . ? S1 Bi1 C1 C2 -71.5(10) . . . . ? N1 Bi1 C1 C2 14.6(9) . . . . ? S2 Bi1 C1 C2 -160.6(10) . . . . ? C6 C1 C2 C3 -2(2) . . . . ? Bi1 C1 C2 C3 -178.9(11) . . . . ? C6 C1 C2 C7 -178.2(14) . . . . ? Bi1 C1 C2 C7 4.7(17) . . . . ? C1 C2 C3 C4 1(2) . . . . ? C7 C2 C3 C4 177.7(14) . . . . ? C2 C3 C4 C5 1(3) . . . . ? C3 C4 C5 C6 -3(3) . . . . ? C2 C1 C6 C5 0(2) . . . . ? Bi1 C1 C6 C5 177.0(11) . . . . ? C4 C5 C6 C1 2(2) . . . . ? C1 C2 C7 N1 -36.4(19) . . . . ? C3 C2 C7 N1 147.1(13) . . . . ? N2 Bi2 C10 C11 14.8(9) . . . . ? S2 Bi2 C10 C11 -71.3(9) . . . . ? S1 Bi2 C10 C11 -160.5(9) . . . . ? N2 Bi2 C10 C15 -167.7(11) . . . . ? S2 Bi2 C10 C15 106.2(10) . . . . ? S1 Bi2 C10 C15 17.0(10) . . . . ? C15 C10 C11 C12 2.2(19) . . . . ? Bi2 C10 C11 C12 179.8(10) . . . . ? C15 C10 C11 C16 -174.9(12) . . . . ? Bi2 C10 C11 C16 2.7(16) . . . . ? C10 C11 C12 C13 -2(2) . . . . ? C16 C11 C12 C13 174.7(14) . . . . ? C11 C12 C13 C14 2(2) . . . . ? C12 C13 C14 C15 -2(2) . . . . ? C11 C10 C15 C14 -2.0(19) . . . . ? Bi2 C10 C15 C14 -179.4(10) . . . . ? C13 C14 C15 C10 2(2) . . . . ? C10 C11 C16 N2 -32.5(17) . . . . ? C12 C11 C16 N2 150.5(12) . . . . ? C32 C30 C31 C32 1(9) 2_667 . . . ? C30 C31 C32 C30 -1(8) . . . 2_667 ? C2 C7 N1 C9 163.6(12) . . . . ? C2 C7 N1 C8 -71.4(15) . . . . ? C2 C7 N1 Bi1 42.0(13) . . . . ? C1 Bi1 N1 C9 -151.0(11) . . . . ? S1 Bi1 N1 C9 -54.5(10) . . . . ? S2 Bi1 N1 C9 -134.6(10) . . . . ? C1 Bi1 N1 C8 83.2(10) . . . . ? S1 Bi1 N1 C8 179.7(10) . . . . ? S2 Bi1 N1 C8 99.6(13) . . . . ? C1 Bi1 N1 C7 -30.3(8) . . . . ? S1 Bi1 N1 C7 66.2(8) . . . . ? S2 Bi1 N1 C7 -13.9(15) . . . . ? C11 C16 N2 C17 163.1(11) . . . . ? C11 C16 N2 C18 -71.6(13) . . . . ? C11 C16 N2 Bi2 39.3(11) . . . . ? C10 Bi2 N2 C17 -152.6(10) . . . . ? S2 Bi2 N2 C17 -60.9(9) . . . . ? S1 Bi2 N2 C17 -136.5(9) . . . . ? C10 Bi2 N2 C16 -29.5(8) . . . . ? S2 Bi2 N2 C16 62.3(7) . . . . ? S1 Bi2 N2 C16 -13.3(14) . . . . ? C10 Bi2 N2 C18 87.6(8) . . . . ? S2 Bi2 N2 C18 179.4(8) . . . . ? S1 Bi2 N2 C18 103.8(11) . . . . ? C1 Bi1 S1 W1 169.1(3) . . . . ? N1 Bi1 S1 W1 96.0(3) . . . . ? S2 Bi1 S1 W1 -100.96(12) . . . . ? C1 Bi1 S1 Bi2 -86.7(3) . . . . ? N1 Bi1 S1 Bi2 -159.8(3) . . . . ? S2 Bi1 S1 Bi2 3.20(9) . . . . ? C10 Bi2 S1 Bi1 87.2(3) . . . . ? N2 Bi2 S1 Bi1 71.8(9) . . . . ? S2 Bi2 S1 Bi1 -3.44(9) . . . . ? C10 Bi2 S1 W1 -158.2(3) . . . . ? N2 Bi2 S1 W1 -173.6(8) . . . . ? S2 Bi2 S1 W1 111.17(11) . . . . ? C10 Bi2 S2 W2 162.0(3) . . . . ? N2 Bi2 S2 W2 89.5(3) . . . . ? S1 Bi2 S2 W2 -106.96(13) . . . . ? C10 Bi2 S2 Bi1 -87.9(3) . . . . ? N2 Bi2 S2 Bi1 -160.4(2) . . . . ? S1 Bi2 S2 Bi1 3.18(9) . . . . ? C28 W2 S2 Bi2 171.6(6) . . . . ? C26 W2 S2 Bi2 -12.6(4) . . . . ? C24 W2 S2 Bi2 80.8(5) . . . . ? C27 W2 S2 Bi2 -100.1(5) . . . . ? C28 W2 S2 Bi1 70.2(6) . . . . ? C26 W2 S2 Bi1 -114.1(4) . . . . ? C24 W2 S2 Bi1 -20.7(5) . . . . ? C27 W2 S2 Bi1 158.4(5) . . . . ? C1 Bi1 S2 Bi2 92.2(3) . . . . ? S1 Bi1 S2 Bi2 -3.42(9) . . . . ? N1 Bi1 S2 Bi2 76.5(9) . . . . ? C1 Bi1 S2 W2 -143.9(3) . . . . ? S1 Bi1 S2 W2 120.52(11) . . . . ? N1 Bi1 S2 W2 -159.6(9) . . . . ? Bi1 S1 W1 C23 -26.2(4) . . . . ? Bi2 S1 W1 C23 -122.9(4) . . . . ? Bi1 S1 W1 C22 60.2(4) . . . . ? Bi2 S1 W1 C22 -36.6(4) . . . . ? Bi1 S1 W1 C21 150.4(4) . . . . ? Bi2 S1 W1 C21 53.6(4) . . . . ? Bi1 S1 W1 C20 -117.6(4) . . . . ? Bi2 S1 W1 C20 145.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.444 _refine_diff_density_min -1.406 _refine_diff_density_rms 0.233 # Attachment 'Compound 5 - CCDC 652894.cif' data_358rich _database_code_depnum_ccdc_archive 'CCDC 652894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Bi Br N2' _chemical_formula_sum 'C18 H24 Bi Br N2' _chemical_formula_weight 557.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5102(9) _cell_length_b 16.2013(16) _cell_length_c 12.4073(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.972(2) _cell_angle_gamma 90.00 _cell_volume 1911.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4853 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 23.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 11.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.096 _exptl_absorpt_correction_T_max 0.325 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 20240 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3894 _reflns_number_gt 3493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0194P)^2^+4.0116P] 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 3894 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.08094(2) 0.150548(14) 0.438389(19) 0.03977(9) Uani 1 1 d . . . Br1 Br 0.25821(8) 0.09444(5) 0.27110(6) 0.0608(2) Uani 1 1 d . . . C1 C 0.2368(7) 0.2526(4) 0.4724(5) 0.0438(15) Uani 1 1 d . . . C2 C 0.2136(7) 0.3295(4) 0.4230(5) 0.0482(16) Uani 1 1 d . . . C3 C 0.3087(8) 0.3930(4) 0.4426(6) 0.0594(19) Uani 1 1 d . . . H3 H 0.2923 0.4448 0.4127 0.071 Uiso 1 1 calc R . . C4 C 0.4271(8) 0.3800(5) 0.5059(7) 0.067(2) Uani 1 1 d . . . H4 H 0.4915 0.4226 0.5161 0.081 Uiso 1 1 calc R . . C5 C 0.4506(7) 0.3061(5) 0.5533(6) 0.062(2) Uani 1 1 d . . . H5 H 0.5297 0.2985 0.5973 0.074 Uiso 1 1 calc R . . C6 C 0.3559(7) 0.2409(4) 0.5362(6) 0.0513(17) Uani 1 1 d . . . H6 H 0.3732 0.1897 0.5678 0.062 Uiso 1 1 calc R . . C7 C 0.0855(8) 0.3406(5) 0.3507(6) 0.061(2) Uani 1 1 d . . . H7A H 0.0869 0.3956 0.3199 0.073 Uiso 1 1 calc R . . H7B H 0.0895 0.3012 0.2919 0.073 Uiso 1 1 calc R . . C8 C -0.0718(9) 0.3991(5) 0.4760(7) 0.076(2) Uani 1 1 d . . . H8A H 0.0071 0.4079 0.5239 0.114 Uiso 1 1 calc R . . H8B H -0.1543 0.3885 0.5173 0.114 Uiso 1 1 calc R . . H8C H -0.0867 0.4474 0.4325 0.114 Uiso 1 1 calc R . . C9 C -0.1629(9) 0.3166(6) 0.3310(7) 0.081(3) Uani 1 1 d . . . H9A H -0.1716 0.3637 0.2845 0.122 Uiso 1 1 calc R . . H9B H -0.2481 0.3097 0.3704 0.122 Uiso 1 1 calc R . . H9C H -0.1462 0.2681 0.2886 0.122 Uiso 1 1 calc R . . C10 C 0.1741(6) 0.0614(4) 0.5594(5) 0.0405(14) Uani 1 1 d . . . C11 C 0.0939(7) 0.0485(4) 0.6509(5) 0.0445(15) Uani 1 1 d . . . C12 C 0.1401(8) -0.0059(4) 0.7289(6) 0.0573(19) Uani 1 1 d . . . H12 H 0.0858 -0.0145 0.7896 0.069 Uiso 1 1 calc R . . C13 C 0.2650(9) -0.0479(5) 0.7188(7) 0.068(2) Uani 1 1 d . . . H13 H 0.2947 -0.0848 0.7720 0.082 Uiso 1 1 calc R . . C14 C 0.3446(8) -0.0350(5) 0.6305(7) 0.069(2) Uani 1 1 d . . . H14 H 0.4298 -0.0625 0.6237 0.083 Uiso 1 1 calc R . . C15 C 0.2994(7) 0.0192(4) 0.5501(6) 0.0573(19) Uani 1 1 d . . . H15 H 0.3541 0.0270 0.4895 0.069 Uiso 1 1 calc R . . C16 C -0.0477(7) 0.0899(4) 0.6591(6) 0.0546(18) Uani 1 1 d . . . H16A H -0.1179 0.0566 0.6218 0.066 Uiso 1 1 calc R . . H16B H -0.0734 0.0931 0.7344 0.066 Uiso 1 1 calc R . . C17 C -0.1936(7) 0.2000(5) 0.5891(7) 0.063(2) Uani 1 1 d . . . H17A H -0.2365 0.1627 0.5381 0.095 Uiso 1 1 calc R . . H17B H -0.1925 0.2546 0.5593 0.095 Uiso 1 1 calc R . . H17C H -0.2465 0.2000 0.6543 0.095 Uiso 1 1 calc R . . C18 C 0.0220(8) 0.2325(4) 0.6850(6) 0.0588(19) Uani 1 1 d . . . H18A H -0.0243 0.2332 0.7532 0.088 Uiso 1 1 calc R . . H18B H 0.0177 0.2866 0.6534 0.088 Uiso 1 1 calc R . . H18C H 0.1186 0.2168 0.6957 0.088 Uiso 1 1 calc R . . N1 N -0.0442(6) 0.3292(3) 0.4072(5) 0.0544(15) Uani 1 1 d . . . N2 N -0.0481(5) 0.1730(3) 0.6130(4) 0.0448(13) 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 0.04271(14) 0.03778(14) 0.03880(15) -0.00014(11) -0.00013(9) -0.00035(11) Br1 0.0732(5) 0.0567(5) 0.0532(4) 0.0010(4) 0.0212(4) -0.0052(4) C1 0.052(4) 0.040(4) 0.039(4) -0.004(3) 0.005(3) -0.003(3) C2 0.066(4) 0.044(4) 0.035(4) 0.005(3) 0.010(3) 0.006(3) C3 0.081(5) 0.035(4) 0.062(5) 0.003(3) 0.017(4) -0.009(4) C4 0.068(5) 0.063(5) 0.071(5) -0.015(4) 0.015(4) -0.026(4) C5 0.051(4) 0.069(5) 0.066(5) -0.004(4) 0.000(4) -0.011(4) C6 0.054(4) 0.047(4) 0.053(4) 0.006(3) 0.000(3) -0.003(3) C7 0.082(5) 0.058(5) 0.043(4) 0.008(4) -0.001(4) 0.002(4) C8 0.092(6) 0.060(5) 0.076(6) -0.008(5) 0.003(5) 0.018(5) C9 0.089(6) 0.082(6) 0.072(6) 0.000(5) -0.027(5) 0.011(5) C10 0.043(3) 0.035(3) 0.043(4) 0.006(3) -0.002(3) -0.001(3) C11 0.056(4) 0.035(3) 0.043(4) 0.001(3) 0.002(3) -0.011(3) C12 0.077(5) 0.050(4) 0.045(4) 0.006(3) 0.002(4) -0.013(4) C13 0.077(5) 0.058(5) 0.069(6) 0.017(4) -0.021(4) -0.007(4) C14 0.059(5) 0.056(5) 0.092(6) 0.011(5) -0.015(4) 0.014(4) C15 0.052(4) 0.052(4) 0.068(5) 0.013(4) 0.009(4) 0.009(3) C16 0.061(4) 0.051(4) 0.052(4) 0.001(3) 0.018(3) -0.007(3) C17 0.049(4) 0.058(5) 0.083(6) -0.004(4) 0.011(4) 0.000(4) C18 0.075(5) 0.051(4) 0.050(4) -0.016(3) -0.002(4) -0.001(4) N1 0.070(4) 0.046(3) 0.047(3) -0.006(3) -0.003(3) 0.011(3) N2 0.045(3) 0.044(3) 0.046(3) 0.001(3) 0.004(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C10 2.254(6) . ? Bi1 C1 2.255(6) . ? Bi1 N2 2.534(5) . ? Bi1 Br1 2.8452(7) . ? C1 C6 1.384(9) . ? C1 C2 1.404(9) . ? C2 C3 1.388(10) . ? C2 C7 1.512(10) . ? C3 C4 1.378(11) . ? C4 C5 1.352(11) . ? C5 C6 1.402(10) . ? C7 N1 1.441(9) . ? C8 N1 1.445(9) . ? C9 N1 1.474(9) . ? C10 C15 1.381(9) . ? C10 C11 1.394(8) . ? C11 C12 1.375(9) . ? C11 C16 1.510(9) . ? C12 C13 1.377(10) . ? C13 C14 1.359(11) . ? C14 C15 1.391(10) . ? C16 N2 1.464(8) . ? C17 N2 1.476(8) . ? C18 N2 1.468(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Bi1 C1 95.5(2) . . ? C10 Bi1 N2 73.3(2) . . ? C1 Bi1 N2 93.5(2) . . ? C10 Bi1 Br1 92.89(16) . . ? C1 Bi1 Br1 88.57(16) . . ? N2 Bi1 Br1 166.19(12) . . ? C6 C1 C2 119.5(6) . . ? C6 C1 Bi1 122.4(5) . . ? C2 C1 Bi1 118.1(5) . . ? C3 C2 C1 119.0(7) . . ? C3 C2 C7 122.1(6) . . ? C1 C2 C7 118.9(6) . . ? C4 C3 C2 120.7(7) . . ? C5 C4 C3 120.7(7) . . ? C4 C5 C6 120.1(7) . . ? C1 C6 C5 120.0(7) . . ? N1 C7 C2 112.6(6) . . ? C15 C10 C11 118.6(6) . . ? C15 C10 Bi1 126.3(5) . . ? C11 C10 Bi1 115.1(4) . . ? C12 C11 C10 119.8(6) . . ? C12 C11 C16 120.8(6) . . ? C10 C11 C16 119.3(6) . . ? C11 C12 C13 121.2(7) . . ? C14 C13 C12 119.4(7) . . ? C13 C14 C15 120.4(7) . . ? C10 C15 C14 120.6(7) . . ? N2 C16 C11 112.3(5) . . ? C7 N1 C8 110.7(6) . . ? C7 N1 C9 111.0(6) . . ? C8 N1 C9 110.0(6) . . ? C16 N2 C18 111.6(6) . . ? C16 N2 C17 110.3(5) . . ? C18 N2 C17 110.1(5) . . ? C16 N2 Bi1 101.8(4) . . ? C18 N2 Bi1 113.2(4) . . ? C17 N2 Bi1 109.7(4) . . ? 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 C10 Bi1 C1 C6 9.7(6) . . . . ? N2 Bi1 C1 C6 83.3(5) . . . . ? Br1 Bi1 C1 C6 -83.0(5) . . . . ? C10 Bi1 C1 C2 -172.8(5) . . . . ? N2 Bi1 C1 C2 -99.3(5) . . . . ? Br1 Bi1 C1 C2 94.4(5) . . . . ? C6 C1 C2 C3 -2.2(10) . . . . ? Bi1 C1 C2 C3 -179.7(5) . . . . ? C6 C1 C2 C7 178.1(6) . . . . ? Bi1 C1 C2 C7 0.6(8) . . . . ? C1 C2 C3 C4 2.6(10) . . . . ? C7 C2 C3 C4 -177.7(7) . . . . ? C2 C3 C4 C5 -2.3(11) . . . . ? C3 C4 C5 C6 1.6(12) . . . . ? C2 C1 C6 C5 1.5(10) . . . . ? Bi1 C1 C6 C5 178.9(5) . . . . ? C4 C5 C6 C1 -1.2(11) . . . . ? C3 C2 C7 N1 -117.9(7) . . . . ? C1 C2 C7 N1 61.8(8) . . . . ? C1 Bi1 C10 C15 -72.4(6) . . . . ? N2 Bi1 C10 C15 -164.4(6) . . . . ? Br1 Bi1 C10 C15 16.5(6) . . . . ? C1 Bi1 C10 C11 108.4(5) . . . . ? N2 Bi1 C10 C11 16.4(4) . . . . ? Br1 Bi1 C10 C11 -162.8(4) . . . . ? C15 C10 C11 C12 -0.5(10) . . . . ? Bi1 C10 C11 C12 178.8(5) . . . . ? C15 C10 C11 C16 -176.1(6) . . . . ? Bi1 C10 C11 C16 3.2(8) . . . . ? C10 C11 C12 C13 0.3(10) . . . . ? C16 C11 C12 C13 175.9(7) . . . . ? C11 C12 C13 C14 0.4(12) . . . . ? C12 C13 C14 C15 -1.0(12) . . . . ? C11 C10 C15 C14 -0.1(11) . . . . ? Bi1 C10 C15 C14 -179.3(5) . . . . ? C13 C14 C15 C10 0.9(12) . . . . ? C12 C11 C16 N2 147.4(6) . . . . ? C10 C11 C16 N2 -37.0(9) . . . . ? C2 C7 N1 C8 73.9(8) . . . . ? C2 C7 N1 C9 -163.7(6) . . . . ? C11 C16 N2 C18 -76.3(7) . . . . ? C11 C16 N2 C17 161.0(6) . . . . ? C11 C16 N2 Bi1 44.7(6) . . . . ? C10 Bi1 N2 C16 -32.6(4) . . . . ? C1 Bi1 N2 C16 -127.2(4) . . . . ? Br1 Bi1 N2 C16 -29.0(8) . . . . ? C10 Bi1 N2 C18 87.3(5) . . . . ? C1 Bi1 N2 C18 -7.4(5) . . . . ? Br1 Bi1 N2 C18 90.9(6) . . . . ? C10 Bi1 N2 C17 -149.4(4) . . . . ? C1 Bi1 N2 C17 116.0(4) . . . . ? Br1 Bi1 N2 C17 -145.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.115 _refine_diff_density_min -1.310 _refine_diff_density_rms 0.115 # Attachment 'Compound 3 - CCDC 653119.cif' data_177rich _database_code_depnum_ccdc_archive 'CCDC 653119' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H48 Bi2 N4 O3' _chemical_formula_sum 'C37 H48 Bi2 N4 O3' _chemical_formula_weight 1014.75 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' 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 17.063(7) _cell_length_b 9.502(4) _cell_length_c 24.891(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.916(7) _cell_angle_gamma 90.00 _cell_volume 3861(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6351 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 9.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.118 _exptl_absorpt_correction_T_max 0.214 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 27069 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6802 _reflns_number_gt 6184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0258P)^2^+16.1683P] 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 6802 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.229 _refine_ls_restrained_S_all 1.229 _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 0.157152(19) 1.10517(3) 0.003648(13) 0.03486(10) Uani 1 1 d . . . Bi2 Bi 0.27664(2) 0.79019(4) 0.181218(13) 0.04144(11) Uani 1 1 d . . . C1 C 0.0825(5) 0.9077(9) -0.0272(3) 0.0352(19) Uani 1 1 d . . . C2 C 0.0171(5) 0.9197(9) -0.0755(4) 0.040(2) Uani 1 1 d . . . C3 C -0.0295(6) 0.8016(11) -0.0976(4) 0.054(3) Uani 1 1 d . . . H3 H -0.0729 0.8098 -0.1303 0.064 Uiso 1 1 calc R . . C4 C -0.0116(7) 0.6706(11) -0.0711(5) 0.062(3) Uani 1 1 d . . . H4 H -0.0430 0.5921 -0.0860 0.074 Uiso 1 1 calc R . . C5 C 0.0524(6) 0.6591(10) -0.0234(5) 0.055(3) Uani 1 1 d . . . H5 H 0.0649 0.5726 -0.0055 0.066 Uiso 1 1 calc R . . C6 C 0.0983(6) 0.7763(9) -0.0017(4) 0.047(2) Uani 1 1 d . . . H6 H 0.1413 0.7672 0.0311 0.056 Uiso 1 1 calc R . . C7 C -0.0061(5) 1.0614(10) -0.1033(4) 0.047(2) Uani 1 1 d . . . H7A H -0.0375 1.0476 -0.1422 0.056 Uiso 1 1 calc R . . H7B H -0.0405 1.1112 -0.0847 0.056 Uiso 1 1 calc R . . C8 C 0.1063(6) 1.1023(11) -0.1428(4) 0.059(3) Uani 1 1 d . . . H8A H 0.1201 1.0043 -0.1377 0.088 Uiso 1 1 calc R . . H8B H 0.1553 1.1563 -0.1387 0.088 Uiso 1 1 calc R . . H8C H 0.0695 1.1169 -0.1797 0.088 Uiso 1 1 calc R . . C9 C 0.0474(7) 1.2986(10) -0.1083(4) 0.061(3) Uani 1 1 d . . . H9A H 0.0968 1.3511 -0.1044 0.092 Uiso 1 1 calc R . . H9B H 0.0224 1.3290 -0.0803 0.092 Uiso 1 1 calc R . . H9C H 0.0102 1.3141 -0.1450 0.092 Uiso 1 1 calc R . . C10 C 0.2631(5) 1.0272(9) -0.0262(3) 0.040(2) Uani 1 1 d . . . C11 C 0.3305(6) 1.1174(10) -0.0233(4) 0.047(2) Uani 1 1 d . . . C12 C 0.3954(6) 1.0659(13) -0.0409(4) 0.063(3) Uani 1 1 d . . . H12 H 0.4396 1.1248 -0.0392 0.076 Uiso 1 1 calc R . . C13 C 0.3964(7) 0.9316(14) -0.0608(5) 0.072(3) Uani 1 1 d . . . H13 H 0.4410 0.9003 -0.0719 0.086 Uiso 1 1 calc R . . C14 C 0.3316(7) 0.8438(11) -0.0642(5) 0.063(3) Uani 1 1 d . . . H14 H 0.3313 0.7534 -0.0786 0.076 Uiso 1 1 calc R . . C15 C 0.2658(6) 0.8901(10) -0.0461(4) 0.050(2) Uani 1 1 d . . . H15 H 0.2229 0.8285 -0.0473 0.061 Uiso 1 1 calc R . . C16 C 0.3287(6) 1.2683(11) -0.0044(4) 0.054(3) Uani 1 1 d . . . H16A H 0.3182 1.2696 0.0318 0.065 Uiso 1 1 calc R . . H16B H 0.3819 1.3108 0.0001 0.065 Uiso 1 1 calc R . . C17 C 0.2527(8) 1.4831(14) -0.0187(7) 0.108(5) Uani 1 1 d . . . H17A H 0.2525 1.4667 0.0193 0.163 Uiso 1 1 calc R . . H17B H 0.2008 1.5217 -0.0398 0.163 Uiso 1 1 calc R . . H17C H 0.2956 1.5483 -0.0190 0.163 Uiso 1 1 calc R . . C18 C 0.2897(8) 1.3775(14) -0.0953(5) 0.089(4) Uani 1 1 d . . . H18A H 0.2492 1.4361 -0.1200 0.133 Uiso 1 1 calc R . . H18B H 0.2932 1.2897 -0.1135 0.133 Uiso 1 1 calc R . . H18C H 0.3419 1.4239 -0.0859 0.133 Uiso 1 1 calc R . . C19 C 0.1909(5) 0.8449(10) 0.2331(4) 0.044(2) Uani 1 1 d . . . C20 C 0.1517(9) 0.7354(12) 0.2513(6) 0.091(5) Uani 1 1 d . . . C21 C 0.0947(9) 0.7653(16) 0.2814(7) 0.113(6) Uani 1 1 d . . . H21 H 0.0681 0.6918 0.2935 0.135 Uiso 1 1 calc R . . C22 C 0.0787(8) 0.9001(16) 0.2926(5) 0.082(4) Uani 1 1 d . . . H22 H 0.0429 0.9182 0.3137 0.098 Uiso 1 1 calc R . . C23 C 0.1148(7) 1.0093(14) 0.2732(5) 0.073(3) Uani 1 1 d . . . H23 H 0.1017 1.1017 0.2794 0.087 Uiso 1 1 calc R . . C24 C 0.1712(6) 0.9814(12) 0.2442(4) 0.061(3) Uani 1 1 d . . . H24 H 0.1966 1.0563 0.2319 0.073 Uiso 1 1 calc R . . C28 C 0.3899(5) 0.8004(9) 0.2549(4) 0.040(2) Uani 1 1 d . . . C29 C 0.4640(6) 0.7486(9) 0.2492(4) 0.045(2) Uani 1 1 d . . . C30 C 0.5344(6) 0.7493(10) 0.2959(5) 0.056(3) Uani 1 1 d . . . H30 H 0.5835 0.7148 0.2922 0.067 Uiso 1 1 calc R . . C31 C 0.5313(7) 0.7999(11) 0.3466(4) 0.061(3) Uani 1 1 d . . . H31 H 0.5780 0.7979 0.3773 0.073 Uiso 1 1 calc R . . C32 C 0.4592(6) 0.8540(10) 0.3524(4) 0.053(3) Uani 1 1 d . . . H32 H 0.4574 0.8883 0.3870 0.063 Uiso 1 1 calc R . . C33 C 0.3911(6) 0.8571(9) 0.3080(3) 0.043(2) Uani 1 1 d . . . H33 H 0.3437 0.8976 0.3123 0.051 Uiso 1 1 calc R . . C34 C 0.4682(7) 0.6869(11) 0.1939(4) 0.061(3) Uani 1 1 d . . . H34A H 0.5251 0.6773 0.1946 0.074 Uiso 1 1 calc R . . H34B H 0.4438 0.5939 0.1891 0.074 Uiso 1 1 calc R . . C35 C 0.4122(9) 0.6982(15) 0.0930(5) 0.096(4) Uani 1 1 d . . . H35A H 0.4625 0.6547 0.0918 0.144 Uiso 1 1 calc R . . H35B H 0.3942 0.7632 0.0624 0.144 Uiso 1 1 calc R . . H35C H 0.3712 0.6272 0.0901 0.144 Uiso 1 1 calc R . . C36 C 0.4695(8) 0.9081(13) 0.1459(5) 0.082(4) Uani 1 1 d . . . H36A H 0.4737 0.9594 0.1799 0.123 Uiso 1 1 calc R . . H36B H 0.4398 0.9633 0.1142 0.123 Uiso 1 1 calc R . . H36C H 0.5234 0.8886 0.1431 0.123 Uiso 1 1 calc R . . C37 C 0.2566(5) 1.0728(10) 0.1215(3) 0.041(2) Uani 1 1 d . . . N1 N 0.0671(4) 1.1472(7) -0.1007(3) 0.0406(17) Uani 1 1 d . . . N2 N 0.2665(5) 1.3510(9) -0.0440(4) 0.062(2) Uani 1 1 d . . . N3 N 0.2386(5) 0.5526(8) 0.2294(4) 0.051(2) Uani 1 1 d . . . N4 N 0.4259(5) 0.7747(9) 0.1468(4) 0.060(2) Uani 1 1 d . . . O1 O 0.2084(4) 0.9854(6) 0.0857(2) 0.0447(15) Uani 1 1 d . . . O2 O 0.2932(4) 1.0218(7) 0.1706(2) 0.0531(17) Uani 1 1 d . . . O3 O 0.2667(4) 1.1968(7) 0.1091(3) 0.0604(19) Uani 1 1 d . . . C27 C 0.2793(12) 0.533(2) 0.2864(7) 0.183(11) Uani 1 1 d . . . H27A H 0.2651 0.6077 0.3078 0.274 Uiso 1 1 calc R . . H27B H 0.3374 0.5333 0.2920 0.274 Uiso 1 1 calc R . . H27C H 0.2633 0.4444 0.2986 0.274 Uiso 1 1 calc R . . C25 C 0.1533(9) 0.5735(18) 0.2208(9) 0.145(8) Uani 1 1 d . . . H25A H 0.1304 0.5011 0.2393 0.175 Uiso 1 1 calc R . . H25B H 0.1236 0.5750 0.1811 0.175 Uiso 1 1 calc R . . C26 C 0.2508(15) 0.4301(17) 0.2015(11) 0.204(13) Uani 1 1 d . . . H26A H 0.3074 0.4028 0.2148 0.305 Uiso 1 1 calc R . . H26B H 0.2364 0.4478 0.1619 0.305 Uiso 1 1 calc R . . H26C H 0.2171 0.3559 0.2087 0.305 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 0.03940(19) 0.03043(18) 0.03225(17) 0.00085(13) 0.00649(13) -0.00066(14) Bi2 0.0417(2) 0.0454(2) 0.03283(18) 0.00052(15) 0.00390(14) -0.00150(16) C1 0.028(4) 0.035(5) 0.042(5) 0.001(4) 0.009(4) -0.001(4) C2 0.039(5) 0.037(5) 0.047(5) -0.005(4) 0.018(4) -0.004(4) C3 0.041(5) 0.061(7) 0.055(6) -0.015(5) 0.008(5) -0.009(5) C4 0.059(7) 0.047(6) 0.081(8) -0.013(6) 0.025(6) -0.015(5) C5 0.060(7) 0.038(5) 0.073(7) 0.001(5) 0.028(6) -0.004(5) C6 0.052(6) 0.042(5) 0.048(5) 0.005(4) 0.016(5) -0.005(4) C7 0.043(5) 0.054(6) 0.038(5) 0.003(4) 0.004(4) 0.003(4) C8 0.063(7) 0.070(7) 0.041(5) 0.003(5) 0.010(5) -0.008(6) C9 0.068(7) 0.050(6) 0.059(7) 0.007(5) 0.006(5) 0.006(5) C10 0.039(5) 0.041(5) 0.038(5) 0.011(4) 0.008(4) 0.001(4) C11 0.048(6) 0.051(6) 0.040(5) 0.013(4) 0.010(4) -0.004(5) C12 0.045(6) 0.088(9) 0.063(7) 0.011(6) 0.026(5) -0.012(6) C13 0.056(7) 0.088(9) 0.077(8) 0.014(7) 0.029(6) 0.018(7) C14 0.070(7) 0.044(6) 0.087(8) 0.010(6) 0.041(6) 0.019(5) C15 0.046(5) 0.047(6) 0.060(6) 0.011(5) 0.018(5) -0.002(5) C16 0.047(6) 0.066(7) 0.049(6) -0.001(5) 0.013(5) -0.023(5) C17 0.090(10) 0.068(9) 0.162(15) -0.029(10) 0.028(10) -0.005(8) C18 0.097(10) 0.085(10) 0.071(8) 0.028(7) 0.005(7) -0.018(8) C19 0.037(5) 0.049(6) 0.044(5) 0.000(4) 0.007(4) 0.003(4) C20 0.122(12) 0.048(7) 0.131(12) 0.021(8) 0.083(10) 0.020(7) C21 0.107(11) 0.093(11) 0.181(16) 0.050(11) 0.109(12) 0.030(9) C22 0.074(8) 0.102(11) 0.078(9) -0.002(8) 0.037(7) 0.024(8) C23 0.070(8) 0.078(9) 0.067(8) -0.022(7) 0.015(6) 0.010(7) C24 0.061(7) 0.056(7) 0.061(7) -0.013(6) 0.010(5) -0.002(5) C28 0.036(5) 0.043(5) 0.039(5) 0.008(4) 0.005(4) -0.003(4) C29 0.050(6) 0.029(5) 0.054(6) 0.001(4) 0.010(5) -0.006(4) C30 0.040(5) 0.049(6) 0.071(7) 0.015(5) 0.004(5) 0.001(4) C31 0.059(7) 0.061(7) 0.047(6) 0.018(5) -0.009(5) -0.006(5) C32 0.058(6) 0.055(6) 0.038(5) -0.005(5) 0.002(5) -0.014(5) C33 0.049(5) 0.048(5) 0.028(4) 0.005(4) 0.007(4) 0.008(4) C34 0.061(7) 0.056(7) 0.071(7) -0.003(6) 0.026(6) 0.007(5) C35 0.135(12) 0.099(11) 0.060(8) -0.020(7) 0.039(8) -0.005(9) C36 0.107(10) 0.074(9) 0.076(8) 0.006(7) 0.045(8) -0.012(8) C37 0.040(5) 0.055(6) 0.028(5) 0.014(4) 0.006(4) 0.009(4) N1 0.043(4) 0.038(4) 0.041(4) 0.002(3) 0.012(3) 0.001(3) N2 0.061(6) 0.048(5) 0.072(6) -0.004(5) 0.010(5) -0.008(4) N3 0.038(4) 0.044(5) 0.069(6) 0.000(4) 0.012(4) 0.004(4) N4 0.071(6) 0.055(5) 0.059(5) 0.000(4) 0.025(5) 0.001(5) O1 0.058(4) 0.041(4) 0.029(3) 0.004(3) 0.002(3) -0.004(3) O2 0.067(4) 0.056(4) 0.035(3) 0.006(3) 0.013(3) -0.015(3) O3 0.078(5) 0.047(4) 0.045(4) 0.013(3) 0.002(3) -0.017(4) C27 0.20(2) 0.19(2) 0.108(14) 0.066(14) -0.031(13) -0.123(17) C25 0.070(10) 0.132(15) 0.22(2) 0.086(15) 0.025(11) -0.011(10) C26 0.33(3) 0.068(11) 0.33(3) 0.002(15) 0.28(3) 0.007(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 C10 2.269(9) . ? Bi1 C1 2.272(8) . ? Bi1 O1 2.280(5) . ? Bi1 N1 2.635(7) . ? Bi2 O2 2.245(6) . ? Bi2 C28 2.247(8) . ? Bi2 C19 2.274(9) . ? Bi2 N3 2.722(8) . ? C1 C2 1.387(11) . ? C1 C6 1.391(12) . ? C2 C3 1.393(12) . ? C2 C7 1.513(12) . ? C3 C4 1.400(14) . ? C3 H3 0.9300 . ? C4 C5 1.365(14) . ? C4 H4 0.9300 . ? C5 C6 1.377(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.478(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.462(12) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.477(11) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.400(13) . ? C10 C11 1.420(12) . ? C11 C12 1.393(14) . ? C11 C16 1.512(14) . ? C12 C13 1.370(16) . ? C12 H12 0.9300 . ? C13 C14 1.369(15) . ? C13 H13 0.9300 . ? C14 C15 1.396(13) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N2 1.450(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N2 1.453(15) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N2 1.464(14) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.382(14) . ? C19 C24 1.388(14) . ? C20 C21 1.419(16) . ? C20 C25 1.72(2) . ? C21 C22 1.356(18) . ? C21 H21 0.9300 . ? C22 C23 1.365(17) . ? C22 H22 0.9300 . ? C23 C24 1.386(15) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C28 C29 1.401(12) . ? C28 C33 1.421(12) . ? C29 C30 1.408(13) . ? C29 C34 1.517(13) . ? C30 C31 1.366(14) . ? C30 H30 0.9300 . ? C31 C32 1.379(14) . ? C31 H31 0.9300 . ? C32 C33 1.351(12) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 N4 1.448(13) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 N4 1.481(13) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 N4 1.473(13) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 O3 1.243(10) . ? C37 O2 1.293(9) . ? C37 O1 1.317(10) . ? N3 C27 1.400(16) . ? N3 C26 1.401(17) . ? N3 C25 1.422(16) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C10 Bi1 C1 92.3(3) . . ? C10 Bi1 O1 89.7(3) . . ? C1 Bi1 O1 85.5(3) . . ? C10 Bi1 N1 91.1(3) . . ? C1 Bi1 N1 71.5(3) . . ? O1 Bi1 N1 157.0(2) . . ? O2 Bi2 C28 86.9(3) . . ? O2 Bi2 C19 88.1(3) . . ? C28 Bi2 C19 94.0(3) . . ? O2 Bi2 N3 156.9(2) . . ? C28 Bi2 N3 86.3(3) . . ? C19 Bi2 N3 70.4(3) . . ? C2 C1 C6 118.0(8) . . ? C2 C1 Bi1 117.1(6) . . ? C6 C1 Bi1 124.9(6) . . ? C1 C2 C3 120.0(8) . . ? C1 C2 C7 120.4(8) . . ? C3 C2 C7 119.5(8) . . ? C2 C3 C4 120.6(9) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.4(9) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 119.7(10) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 122.3(9) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? N1 C7 C2 111.4(7) . . ? N1 C7 H7A 109.3 . . ? C2 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C2 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.0(8) . . ? C15 C10 Bi1 122.1(6) . . ? C11 C10 Bi1 119.8(7) . . ? C12 C11 C10 118.6(9) . . ? C12 C11 C16 121.4(9) . . ? C10 C11 C16 119.9(8) . . ? C13 C12 C11 122.3(10) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C14 C13 C12 119.7(10) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 119.9(10) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 121.3(9) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? N2 C16 C11 112.3(8) . . ? N2 C16 H16A 109.1 . . ? C11 C16 H16A 109.1 . . ? N2 C16 H16B 109.1 . . ? C11 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 118.0(9) . . ? C20 C19 Bi2 117.8(7) . . ? C24 C19 Bi2 124.1(8) . . ? C19 C20 C21 119.6(11) . . ? C19 C20 C25 117.2(11) . . ? C21 C20 C25 120.9(12) . . ? C22 C21 C20 120.6(12) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.4(12) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 119.5(12) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C19 121.9(11) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.1 . . ? C29 C28 C33 117.3(8) . . ? C29 C28 Bi2 119.2(6) . . ? C33 C28 Bi2 123.5(6) . . ? C28 C29 C30 119.5(9) . . ? C28 C29 C34 120.7(8) . . ? C30 C29 C34 119.8(9) . . ? C31 C30 C29 120.8(10) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 C32 120.2(9) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C33 C32 C31 120.2(9) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C28 121.9(9) . . ? C32 C33 H33 119.1 . . ? C28 C33 H33 119.1 . . ? N4 C34 C29 111.5(8) . . ? N4 C34 H34A 109.3 . . ? C29 C34 H34A 109.3 . . ? N4 C34 H34B 109.3 . . ? C29 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? N4 C35 H35A 109.5 . . ? N4 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N4 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N4 C36 H36A 109.5 . . ? N4 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N4 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O3 C37 O2 121.8(9) . . ? O3 C37 O1 122.3(7) . . ? O2 C37 O1 115.9(8) . . ? C8 N1 C9 109.1(8) . . ? C8 N1 C7 111.5(7) . . ? C9 N1 C7 111.9(7) . . ? C8 N1 Bi1 113.9(5) . . ? C9 N1 Bi1 108.6(5) . . ? C7 N1 Bi1 101.7(5) . . ? C16 N2 C17 110.7(10) . . ? C16 N2 C18 110.8(9) . . ? C17 N2 C18 110.4(10) . . ? C27 N3 C26 106.8(15) . . ? C27 N3 C25 110.8(14) . . ? C26 N3 C25 109.6(14) . . ? C27 N3 Bi2 116.5(8) . . ? C26 N3 Bi2 112.4(8) . . ? C25 N3 Bi2 100.5(7) . . ? C34 N4 C36 111.8(9) . . ? C34 N4 C35 111.0(9) . . ? C36 N4 C35 110.9(9) . . ? C37 O1 Bi1 107.0(5) . . ? C37 O2 Bi2 115.9(6) . . ? N3 C27 H27A 109.5 . . ? N3 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N3 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C25 C20 101.8(12) . . ? N3 C25 H25A 111.4 . . ? C20 C25 H25A 111.4 . . ? N3 C25 H25B 111.4 . . ? C20 C25 H25B 111.4 . . ? H25A C25 H25B 109.3 . . ? N3 C26 H26A 109.5 . . ? N3 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N3 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 C10 Bi1 C1 C2 -105.8(6) . . . . ? O1 Bi1 C1 C2 164.6(6) . . . . ? N1 Bi1 C1 C2 -15.5(6) . . . . ? C10 Bi1 C1 C6 73.4(8) . . . . ? O1 Bi1 C1 C6 -16.1(7) . . . . ? N1 Bi1 C1 C6 163.8(8) . . . . ? C6 C1 C2 C3 -1.3(13) . . . . ? Bi1 C1 C2 C3 178.0(7) . . . . ? C6 C1 C2 C7 176.5(8) . . . . ? Bi1 C1 C2 C7 -4.2(10) . . . . ? C1 C2 C3 C4 0.8(14) . . . . ? C7 C2 C3 C4 -176.9(9) . . . . ? C2 C3 C4 C5 -0.3(15) . . . . ? C3 C4 C5 C6 0.2(15) . . . . ? C4 C5 C6 C1 -0.7(15) . . . . ? C2 C1 C6 C5 1.3(14) . . . . ? Bi1 C1 C6 C5 -178.0(7) . . . . ? C1 C2 C7 N1 37.7(11) . . . . ? C3 C2 C7 N1 -144.6(8) . . . . ? C1 Bi1 C10 C15 -8.3(7) . . . . ? O1 Bi1 C10 C15 77.2(7) . . . . ? N1 Bi1 C10 C15 -79.9(7) . . . . ? C1 Bi1 C10 C11 173.5(7) . . . . ? O1 Bi1 C10 C11 -101.0(7) . . . . ? N1 Bi1 C10 C11 102.0(7) . . . . ? C15 C10 C11 C12 0.6(13) . . . . ? Bi1 C10 C11 C12 178.8(7) . . . . ? C15 C10 C11 C16 177.4(8) . . . . ? Bi1 C10 C11 C16 -4.4(11) . . . . ? C10 C11 C12 C13 0.0(15) . . . . ? C16 C11 C12 C13 -176.8(10) . . . . ? C11 C12 C13 C14 0.6(18) . . . . ? C12 C13 C14 C15 -1.7(17) . . . . ? C13 C14 C15 C10 2.3(16) . . . . ? C11 C10 C15 C14 -1.7(14) . . . . ? Bi1 C10 C15 C14 -179.9(7) . . . . ? C12 C11 C16 N2 110.0(10) . . . . ? C10 C11 C16 N2 -66.7(11) . . . . ? O2 Bi2 C19 C20 175.7(9) . . . . ? C28 Bi2 C19 C20 -97.5(10) . . . . ? N3 Bi2 C19 C20 -12.9(9) . . . . ? O2 Bi2 C19 C24 0.4(8) . . . . ? C28 Bi2 C19 C24 87.1(8) . . . . ? N3 Bi2 C19 C24 171.7(9) . . . . ? C24 C19 C20 C21 -1(2) . . . . ? Bi2 C19 C20 C21 -176.9(12) . . . . ? C24 C19 C20 C25 161.7(11) . . . . ? Bi2 C19 C20 C25 -13.9(16) . . . . ? C19 C20 C21 C22 0(3) . . . . ? C25 C20 C21 C22 -162.7(15) . . . . ? C20 C21 C22 C23 3(2) . . . . ? C21 C22 C23 C24 -3(2) . . . . ? C22 C23 C24 C19 1.5(17) . . . . ? C20 C19 C24 C23 0.7(16) . . . . ? Bi2 C19 C24 C23 176.1(8) . . . . ? O2 Bi2 C28 C29 -104.0(7) . . . . ? C19 Bi2 C28 C29 168.2(7) . . . . ? N3 Bi2 C28 C29 98.1(7) . . . . ? O2 Bi2 C28 C33 76.0(7) . . . . ? C19 Bi2 C28 C33 -11.8(8) . . . . ? N3 Bi2 C28 C33 -81.9(7) . . . . ? C33 C28 C29 C30 2.7(13) . . . . ? Bi2 C28 C29 C30 -177.3(6) . . . . ? C33 C28 C29 C34 -179.7(8) . . . . ? Bi2 C28 C29 C34 0.3(11) . . . . ? C28 C29 C30 C31 -0.1(14) . . . . ? C34 C29 C30 C31 -177.8(9) . . . . ? C29 C30 C31 C32 -1.3(15) . . . . ? C30 C31 C32 C33 0.0(15) . . . . ? C31 C32 C33 C28 2.7(15) . . . . ? C29 C28 C33 C32 -4.1(13) . . . . ? Bi2 C28 C33 C32 176.0(7) . . . . ? C28 C29 C34 N4 45.6(12) . . . . ? C30 C29 C34 N4 -136.8(9) . . . . ? C2 C7 N1 C8 78.0(9) . . . . ? C2 C7 N1 C9 -159.5(8) . . . . ? C2 C7 N1 Bi1 -43.7(8) . . . . ? C10 Bi1 N1 C8 3.9(6) . . . . ? C1 Bi1 N1 C8 -88.3(6) . . . . ? O1 Bi1 N1 C8 -88.1(8) . . . . ? C10 Bi1 N1 C9 -117.9(6) . . . . ? C1 Bi1 N1 C9 150.0(6) . . . . ? O1 Bi1 N1 C9 150.2(6) . . . . ? C10 Bi1 N1 C7 123.9(5) . . . . ? C1 Bi1 N1 C7 31.8(5) . . . . ? O1 Bi1 N1 C7 32.0(9) . . . . ? C11 C16 N2 C17 166.0(9) . . . . ? C11 C16 N2 C18 -71.2(11) . . . . ? O2 Bi2 N3 C27 -54.9(15) . . . . ? C28 Bi2 N3 C27 18.2(13) . . . . ? C19 Bi2 N3 C27 -77.4(13) . . . . ? O2 Bi2 N3 C26 -178.7(13) . . . . ? C28 Bi2 N3 C26 -105.6(13) . . . . ? C19 Bi2 N3 C26 158.8(14) . . . . ? O2 Bi2 N3 C25 64.9(12) . . . . ? C28 Bi2 N3 C25 138.0(10) . . . . ? C19 Bi2 N3 C25 42.4(10) . . . . ? C29 C34 N4 C36 69.8(11) . . . . ? C29 C34 N4 C35 -165.8(9) . . . . ? O3 C37 O1 Bi1 1.5(10) . . . . ? O2 C37 O1 Bi1 -178.4(6) . . . . ? C10 Bi1 O1 C37 91.7(6) . . . . ? C1 Bi1 O1 C37 -175.9(6) . . . . ? N1 Bi1 O1 C37 -176.1(6) . . . . ? O3 C37 O2 Bi2 -173.9(7) . . . . ? O1 C37 O2 Bi2 5.9(10) . . . . ? C28 Bi2 O2 C37 159.7(6) . . . . ? C19 Bi2 O2 C37 -106.2(6) . . . . ? N3 Bi2 O2 C37 -127.3(7) . . . . ? C27 N3 C25 C20 68.6(14) . . . . ? C26 N3 C25 C20 -173.8(12) . . . . ? Bi2 N3 C25 C20 -55.2(11) . . . . ? C19 C20 C25 N3 54.0(16) . . . . ? C21 C20 C25 N3 -143.2(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.416 _refine_diff_density_min -1.687 _refine_diff_density_rms 0.140 #============================================================================ data_rw10a _database_code_depnum_ccdc_archive 'CCDC 658669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H25 Bi N2 O, 2(H2 O)' _chemical_formula_sum 'C18 H29 Bi N2 O3' _chemical_formula_weight 530.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.149(2) _cell_length_b 26.827(5) _cell_length_c 8.393(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.610(10) _cell_angle_gamma 90.00 _cell_volume 1952.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 83 _cell_measurement_theta_min 2.361 _cell_measurement_theta_max 13.225 _exptl_crystal_description ? _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 9.048 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst A, 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 5612 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4428 _reflns_number_gt 3432 _reflns_threshold_expression >2\s(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, Crystal Impact' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; The short intermolecular H-H distances are indicating disordered OH2- molecules. 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^)+(0.0634P)^2^+13.9998P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4428 _refine_ls_number_parameters 234 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.027 _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 0.39692(3) 0.086055(10) 0.65899(3) 0.01627(11) Uani 1 1 d . . . O1 O 0.2173(7) 0.0294(2) 0.5677(8) 0.0233(13) Uani 1 1 d . . . H1 H 0.1351 0.0431 0.5095 0.035 Uiso 1 1 calc R . . C1 C 0.4822(10) 0.0722(3) 0.4356(10) 0.0188(16) Uani 1 1 d . . . C2 C 0.6220(10) 0.0932(3) 0.4428(11) 0.0210(17) Uani 1 1 d . . . C3 C 0.6780(10) 0.0877(3) 0.3060(12) 0.0240(18) Uani 1 1 d . . . H3 H 0.7734 0.1025 0.3101 0.029 Uiso 1 1 calc R . . C4 C 0.5942(11) 0.0606(3) 0.1644(12) 0.0266(19) Uani 1 1 d . . . H4 H 0.6324 0.0568 0.0723 0.032 Uiso 1 1 calc R . . C5 C 0.4541(11) 0.0392(3) 0.1596(12) 0.0254(19) Uani 1 1 d . . . H5 H 0.3955 0.0213 0.0627 0.030 Uiso 1 1 calc R . . C6 C 0.3995(10) 0.0439(3) 0.2954(11) 0.0216(17) Uani 1 1 d . . . H6 H 0.3061 0.0280 0.2932 0.026 Uiso 1 1 calc R . . C7 C 0.7144(10) 0.1214(3) 0.5947(12) 0.0256(19) Uani 1 1 d . . . H7A H 0.7681 0.0976 0.6845 0.031 Uiso 1 1 calc R . . H7B H 0.7935 0.1416 0.5669 0.031 Uiso 1 1 calc R . . N1 N 0.6149(8) 0.1544(3) 0.6562(9) 0.0232(16) Uani 1 1 d . . . C8 C 0.5639(13) 0.1967(4) 0.5397(14) 0.035(2) Uani 1 1 d . . . H8A H 0.6542 0.2138 0.5268 0.053 Uiso 1 1 calc R . . H8B H 0.5046 0.2200 0.5846 0.053 Uiso 1 1 calc R . . H8C H 0.4990 0.1844 0.4299 0.053 Uiso 1 1 calc R . . C9 C 0.6972(13) 0.1723(4) 0.8274(12) 0.034(2) Uani 1 1 d . . . H9A H 0.7868 0.1920 0.8259 0.051 Uiso 1 1 calc R . . H9B H 0.7318 0.1436 0.9026 0.051 Uiso 1 1 calc R . . H9C H 0.6279 0.1929 0.8675 0.051 Uiso 1 1 calc R . . C10 C 0.2128(9) 0.1413(3) 0.5198(10) 0.0175(16) Uani 1 1 d . . . C11 C 0.1701(10) 0.1824(3) 0.5942(11) 0.0208(17) Uani 1 1 d . . . C12 C 0.0453(11) 0.2109(3) 0.5039(12) 0.0256(19) Uani 1 1 d . . . H12 H 0.0158 0.2388 0.5563 0.031 Uiso 1 1 calc R . . C13 C -0.0378(10) 0.1996(4) 0.3386(12) 0.0264(19) Uani 1 1 d . . . H13 H -0.1233 0.2197 0.2786 0.032 Uiso 1 1 calc R . . C14 C 0.0039(10) 0.1595(4) 0.2624(11) 0.0243(18) Uani 1 1 d . . . H14 H -0.0511 0.1519 0.1485 0.029 Uiso 1 1 calc R . . C15 C 0.1290(9) 0.1298(3) 0.3540(10) 0.0186(16) Uani 1 1 d . . . H15 H 0.1568 0.1014 0.3021 0.022 Uiso 1 1 calc R . . C16 C 0.2542(11) 0.1973(3) 0.7758(11) 0.0242(19) Uani 1 1 d . . . H16A H 0.3532 0.2133 0.7815 0.029 Uiso 1 1 calc R . . H16B H 0.1912 0.2222 0.8117 0.029 Uiso 1 1 calc R . . N2 N 0.2852(9) 0.1551(3) 0.8927(9) 0.0231(15) Uani 1 1 d . . . C17 C 0.1437(13) 0.1317(4) 0.8954(13) 0.035(2) Uani 1 1 d . . . H17A H 0.1678 0.1043 0.9768 0.053 Uiso 1 1 calc R . . H17B H 0.0881 0.1186 0.7833 0.053 Uiso 1 1 calc R . . H17C H 0.0791 0.1563 0.9277 0.053 Uiso 1 1 calc R . . C18 C 0.3730(12) 0.1725(3) 1.0587(11) 0.028(2) Uani 1 1 d . . . H18A H 0.3144 0.1983 1.0945 0.042 Uiso 1 1 calc R . . H18B H 0.4712 0.1864 1.0560 0.042 Uiso 1 1 calc R . . H18C H 0.3930 0.1445 1.1380 0.042 Uiso 1 1 calc R . . O2 O 0.1223(10) -0.0537(3) 0.0275(10) 0.044(2) Uani 1 1 d D . . H20 H 0.102(15) -0.041(4) 0.110(8) 0.066 Uiso 1 1 d D . . H21 H 0.086(16) -0.035(4) -0.056(9) 0.066 Uiso 1 1 d D . . O3 O 0.0040(9) -0.0062(3) 0.2736(8) 0.0342(16) Uani 1 1 d D . . H30 H -0.073(7) -0.018(4) 0.294(11) 0.051 Uiso 1 1 d D . . H31 H 0.062(10) 0.007(4) 0.361(7) 0.051 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01594(16) 0.01671(16) 0.01580(15) 0.00070(13) 0.00455(10) 0.00163(13) O1 0.016(3) 0.029(3) 0.026(3) 0.008(3) 0.007(3) -0.003(2) C1 0.022(4) 0.017(4) 0.020(4) 0.002(3) 0.010(3) 0.003(3) C2 0.017(4) 0.021(4) 0.027(4) 0.008(3) 0.010(3) 0.003(3) C3 0.021(4) 0.023(4) 0.033(5) 0.010(4) 0.014(4) 0.003(4) C4 0.026(5) 0.028(5) 0.033(5) 0.005(4) 0.019(4) 0.010(4) C5 0.029(5) 0.021(4) 0.029(5) -0.005(4) 0.012(4) -0.008(4) C6 0.016(4) 0.020(4) 0.029(4) -0.008(4) 0.007(3) -0.002(3) C7 0.016(4) 0.022(4) 0.034(5) 0.005(4) 0.001(4) 0.001(3) N1 0.016(4) 0.026(4) 0.022(4) 0.000(3) -0.002(3) -0.005(3) C8 0.043(6) 0.022(5) 0.040(6) 0.004(4) 0.011(5) 0.002(4) C9 0.036(6) 0.034(5) 0.024(5) -0.007(4) -0.002(4) -0.003(4) C10 0.013(4) 0.016(4) 0.022(4) -0.001(3) 0.004(3) -0.002(3) C11 0.020(4) 0.022(4) 0.023(4) 0.007(3) 0.009(3) 0.000(3) C12 0.026(5) 0.026(4) 0.031(5) 0.007(4) 0.017(4) 0.010(4) C13 0.019(4) 0.030(5) 0.031(5) 0.014(4) 0.009(4) 0.006(4) C14 0.014(4) 0.036(5) 0.020(4) 0.008(4) -0.001(3) 0.003(3) C15 0.014(4) 0.025(4) 0.016(4) 0.004(3) 0.004(3) 0.007(3) C16 0.034(5) 0.014(4) 0.027(4) -0.011(4) 0.014(4) 0.001(3) N2 0.024(4) 0.023(4) 0.021(4) -0.003(3) 0.005(3) 0.000(3) C17 0.037(6) 0.043(6) 0.030(5) 0.007(5) 0.018(4) -0.005(5) C18 0.038(5) 0.023(4) 0.021(4) -0.003(4) 0.007(4) 0.007(4) O2 0.038(4) 0.059(5) 0.039(4) 0.011(4) 0.017(4) 0.021(4) O3 0.032(4) 0.052(4) 0.024(3) -0.008(3) 0.016(3) -0.013(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 O1 2.189(6) . ? Bi1 C10 2.267(8) . ? Bi1 C1 2.279(8) . ? Bi1 N1 2.715(7) . ? C1 C2 1.382(12) . ? C1 C6 1.402(12) . ? C2 C3 1.406(12) . ? C2 C7 1.491(13) . ? C3 C4 1.395(14) . ? C4 C5 1.394(13) . ? C5 C6 1.389(12) . ? C7 N1 1.477(12) . ? N1 C8 1.472(12) . ? N1 C9 1.473(11) . ? C10 C11 1.384(12) . ? C10 C15 1.393(11) . ? C11 C12 1.382(12) . ? C11 C16 1.525(12) . ? C12 C13 1.386(13) . ? C13 C14 1.367(13) . ? C14 C15 1.406(11) . ? C16 N2 1.466(11) . ? N2 C18 1.446(11) . ? N2 C17 1.446(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Bi1 C10 85.5(3) . . ? O1 Bi1 C1 90.8(3) . . ? C10 Bi1 C1 94.4(3) . . ? O1 Bi1 N1 159.6(2) . . ? C10 Bi1 N1 88.9(3) . . ? C1 Bi1 N1 70.0(3) . . ? C2 C1 C6 120.1(8) . . ? C2 C1 Bi1 116.9(6) . . ? C6 C1 Bi1 123.0(6) . . ? C1 C2 C3 119.7(8) . . ? C1 C2 C7 120.5(8) . . ? C3 C2 C7 119.8(8) . . ? C4 C3 C2 120.4(8) . . ? C5 C4 C3 119.3(8) . . ? C6 C5 C4 120.5(8) . . ? C5 C6 C1 119.9(8) . . ? N1 C7 C2 111.0(7) . . ? C8 N1 C9 110.7(8) . . ? C8 N1 C7 109.3(8) . . ? C9 N1 C7 110.8(7) . . ? C8 N1 Bi1 116.6(6) . . ? C9 N1 Bi1 111.1(6) . . ? C7 N1 Bi1 97.7(5) . . ? C11 C10 C15 118.9(8) . . ? C11 C10 Bi1 124.0(6) . . ? C15 C10 Bi1 116.8(6) . . ? C12 C11 C10 119.8(8) . . ? C12 C11 C16 117.9(8) . . ? C10 C11 C16 122.3(8) . . ? C11 C12 C13 121.5(8) . . ? C14 C13 C12 119.6(8) . . ? C13 C14 C15 119.4(8) . . ? C10 C15 C14 120.9(8) . . ? N2 C16 C11 113.2(7) . . ? C18 N2 C17 110.5(8) . . ? C18 N2 C16 109.0(7) . . ? C17 N2 C16 111.3(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Bi1 C1 C2 -168.3(6) . . . . ? C10 Bi1 C1 C2 106.1(7) . . . . ? N1 Bi1 C1 C2 18.9(6) . . . . ? O1 Bi1 C1 C6 11.8(7) . . . . ? C10 Bi1 C1 C6 -73.8(7) . . . . ? N1 Bi1 C1 C6 -161.0(8) . . . . ? C6 C1 C2 C3 2.4(13) . . . . ? Bi1 C1 C2 C3 -177.5(6) . . . . ? C6 C1 C2 C7 -177.2(8) . . . . ? Bi1 C1 C2 C7 2.9(10) . . . . ? C1 C2 C3 C4 -0.9(13) . . . . ? C7 C2 C3 C4 178.7(8) . . . . ? C2 C3 C4 C5 0.3(13) . . . . ? C3 C4 C5 C6 -1.3(14) . . . . ? C4 C5 C6 C1 2.8(14) . . . . ? C2 C1 C6 C5 -3.4(13) . . . . ? Bi1 C1 C6 C5 176.5(6) . . . . ? C1 C2 C7 N1 -43.1(11) . . . . ? C3 C2 C7 N1 137.3(8) . . . . ? C2 C7 N1 C8 -72.2(9) . . . . ? C2 C7 N1 C9 165.6(8) . . . . ? C2 C7 N1 Bi1 49.5(7) . . . . ? O1 Bi1 N1 C8 58.8(10) . . . . ? C10 Bi1 N1 C8 -15.2(7) . . . . ? C1 Bi1 N1 C8 79.8(7) . . . . ? O1 Bi1 N1 C9 -173.1(7) . . . . ? C10 Bi1 N1 C9 112.8(6) . . . . ? C1 Bi1 N1 C9 -152.1(7) . . . . ? O1 Bi1 N1 C7 -57.3(9) . . . . ? C10 Bi1 N1 C7 -131.3(5) . . . . ? C1 Bi1 N1 C7 -36.3(5) . . . . ? O1 Bi1 C10 C11 124.3(7) . . . . ? C1 Bi1 C10 C11 -145.2(7) . . . . ? N1 Bi1 C10 C11 -75.3(7) . . . . ? O1 Bi1 C10 C15 -49.3(6) . . . . ? C1 Bi1 C10 C15 41.2(6) . . . . ? N1 Bi1 C10 C15 111.1(6) . . . . ? C15 C10 C11 C12 0.5(12) . . . . ? Bi1 C10 C11 C12 -173.0(6) . . . . ? C15 C10 C11 C16 179.3(8) . . . . ? Bi1 C10 C11 C16 5.8(11) . . . . ? C10 C11 C12 C13 -0.8(13) . . . . ? C16 C11 C12 C13 -179.6(8) . . . . ? C11 C12 C13 C14 0.0(14) . . . . ? C12 C13 C14 C15 1.2(13) . . . . ? C11 C10 C15 C14 0.6(12) . . . . ? Bi1 C10 C15 C14 174.5(6) . . . . ? C13 C14 C15 C10 -1.4(13) . . . . ? C12 C11 C16 N2 133.5(8) . . . . ? C10 C11 C16 N2 -45.2(11) . . . . ? C11 C16 N2 C18 176.5(8) . . . . ? C11 C16 N2 C17 -61.3(10) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.809 _refine_diff_density_min -1.930 _refine_diff_density_rms 0.249 # Attachment 'Compound 2 - CCDC 658670.cif' data_lb12 _database_code_depnum_ccdc_archive 'CCDC 658670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H48 Bi2 N4 O' _chemical_formula_sum 'C36 H48 Bi2 N4 O' _chemical_formula_weight 970.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.812(3) _cell_length_b 14.393(9) _cell_length_c 19.969(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.02 _cell_angle_gamma 90.00 _cell_volume 3646(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 4.537 _cell_measurement_theta_max 17.077 _exptl_crystal_description blocks _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.768 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 9.671 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.0856 _exptl_absorpt_correction_T_max 0.2479 _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst A, 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 4022 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.1269 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3185 _reflns_number_gt 1934 _reflns_threshold_expression >2\s(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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0351P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3185 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1258 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 C1 C 0.1739(12) 0.1022(11) 0.3719(7) 0.042(4) Uani 1 1 d . . . C2 C 0.2733(12) 0.1045(12) 0.4110(7) 0.047(4) Uani 1 1 d . . . C3 C 0.2902(16) 0.0453(14) 0.4671(8) 0.067(6) Uani 1 1 d . . . H3 H 0.3566 0.0456 0.4949 0.053(16) Uiso 1 1 calc R . . C4 C 0.2137(18) -0.0122(14) 0.4821(8) 0.069(6) Uani 1 1 d . . . H4 H 0.2276 -0.0506 0.5210 0.053(16) Uiso 1 1 calc R . . C5 C 0.1175(14) -0.0173(12) 0.4438(8) 0.059(5) Uani 1 1 d . . . H5 H 0.0660 -0.0602 0.4546 0.053(16) Uiso 1 1 calc R . . C6 C 0.0966(14) 0.0416(11) 0.3887(7) 0.055(5) Uani 1 1 d . . . H6 H 0.0290 0.0407 0.3621 0.053(16) Uiso 1 1 calc R . . C7 C 0.3610(10) 0.1631(11) 0.3929(7) 0.046(4) Uani 1 1 d . . . H7A H 0.4125 0.1739 0.4339 0.05(2) Uiso 1 1 calc R . . H7B H 0.3977 0.1291 0.3599 0.05(2) Uiso 1 1 calc R . . C8 C 0.4037(11) 0.2972(14) 0.3296(8) 0.067(5) Uani 1 1 d . . . H8A H 0.3806 0.3600 0.3156 0.046(12) Uiso 1 1 calc R . . H8B H 0.4141 0.2607 0.2896 0.046(12) Uiso 1 1 calc R . . H8C H 0.4703 0.3008 0.3603 0.046(12) Uiso 1 1 calc R . . C9 C 0.2950(13) 0.3129(12) 0.4158(7) 0.061(5) Uani 1 1 d . . . H9A H 0.3576 0.3278 0.4481 0.046(12) Uiso 1 1 calc R . . H9B H 0.2431 0.2812 0.4393 0.046(12) Uiso 1 1 calc R . . H9C H 0.2644 0.3704 0.3953 0.046(12) Uiso 1 1 calc R . . C10 C 0.2415(11) 0.1390(11) 0.2205(7) 0.041(4) Uani 1 1 d . . . C11 C 0.2725(10) 0.1885(10) 0.1669(7) 0.039(4) Uani 1 1 d . . . C12 C 0.3446(12) 0.1509(11) 0.1288(7) 0.044(4) Uani 1 1 d . . . H12 H 0.3650 0.1851 0.0921 0.053(16) Uiso 1 1 calc R . . C13 C 0.3877(12) 0.0629(11) 0.1441(8) 0.049(4) Uani 1 1 d . . . H13 H 0.4372 0.0378 0.1177 0.053(16) Uiso 1 1 calc R . . C14 C 0.3588(12) 0.0121(11) 0.1973(6) 0.042(4) Uani 1 1 d . . . H14 H 0.3890 -0.0471 0.2087 0.053(16) Uiso 1 1 calc R . . C15 C 0.2830(11) 0.0507(10) 0.2345(6) 0.039(4) Uani 1 1 d . . . H15 H 0.2598 0.0154 0.2698 0.053(16) Uiso 1 1 calc R . . C16 C 0.2232(11) 0.2823(11) 0.1472(7) 0.045(4) Uani 1 1 d . . . H16A H 0.2441 0.3273 0.1841 0.05(2) Uiso 1 1 calc R . . H16B H 0.2506 0.3053 0.1062 0.05(2) Uiso 1 1 calc R . . C17 C 0.0629(12) 0.3692(10) 0.1241(7) 0.047(4) Uani 1 1 d . . . H17A H 0.0898 0.3998 0.0862 0.046(12) Uiso 1 1 calc R . . H17B H 0.0818 0.4060 0.1653 0.046(12) Uiso 1 1 calc R . . H17C H -0.0140 0.3639 0.1144 0.046(12) Uiso 1 1 calc R . . C18 C 0.0765(11) 0.2228(10) 0.0743(7) 0.046(4) Uani 1 1 d . . . H18A H 0.0943 0.1574 0.0838 0.046(12) Uiso 1 1 calc R . . H18B H 0.1131 0.2448 0.0374 0.046(12) Uiso 1 1 calc R . . H18C H 0.0002 0.2288 0.0611 0.046(12) Uiso 1 1 calc R . . N1 N 0.3245(10) 0.2533(10) 0.3638(6) 0.047(3) Uani 1 1 d . . . N2 N 0.1087(10) 0.2773(7) 0.1338(5) 0.039(3) Uani 1 1 d . . . O1 O 0.0000 0.1184(11) 0.2500 0.053(4) Uani 1 2 d S . . Bi1 Bi 0.13135(5) 0.20374(4) 0.28547(3) 0.03632(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(9) 0.039(9) 0.047(9) 0.003(8) 0.025(8) 0.017(8) C2 0.039(10) 0.050(10) 0.048(9) -0.023(9) -0.007(8) 0.023(9) C3 0.082(15) 0.080(15) 0.032(10) -0.001(10) -0.022(10) 0.027(13) C4 0.115(18) 0.054(12) 0.038(10) -0.002(9) 0.010(12) 0.022(13) C5 0.067(13) 0.063(12) 0.048(10) 0.019(9) 0.011(9) 0.004(11) C6 0.061(12) 0.064(12) 0.041(9) 0.003(9) 0.014(9) -0.004(10) C7 0.016(7) 0.070(12) 0.049(9) -0.024(9) -0.010(7) 0.022(8) C8 0.040(9) 0.079(13) 0.077(11) -0.021(12) -0.006(8) -0.012(12) C9 0.067(12) 0.052(13) 0.059(10) -0.013(9) -0.004(9) 0.012(10) C10 0.039(9) 0.046(10) 0.037(8) 0.006(8) 0.004(7) 0.001(8) C11 0.027(7) 0.029(10) 0.060(9) -0.015(8) 0.001(7) 0.010(7) C12 0.046(10) 0.044(10) 0.043(9) -0.008(8) 0.009(8) -0.012(9) C13 0.049(10) 0.047(11) 0.051(10) -0.002(8) 0.006(8) 0.016(9) C14 0.046(10) 0.043(9) 0.037(9) -0.001(7) 0.006(8) 0.011(8) C15 0.052(10) 0.042(9) 0.023(7) 0.004(7) 0.009(7) 0.005(8) C16 0.056(10) 0.040(10) 0.043(8) -0.009(8) 0.016(7) -0.004(9) C17 0.055(10) 0.047(10) 0.041(9) 0.023(8) 0.013(8) 0.010(9) C18 0.043(9) 0.046(11) 0.047(8) -0.001(8) -0.004(7) -0.006(8) N1 0.044(8) 0.055(8) 0.039(7) -0.013(7) -0.004(6) -0.004(7) N2 0.049(8) 0.028(8) 0.040(6) -0.001(5) 0.006(6) -0.002(6) O1 0.054(10) 0.056(10) 0.045(8) 0.000 -0.009(7) 0.000 Bi1 0.0358(3) 0.0369(3) 0.0362(3) -0.0031(4) 0.00482(19) 0.0024(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.40(2) . ? C1 C2 1.398(19) . ? C1 Bi1 2.268(14) . ? C2 C3 1.40(2) . ? C2 C7 1.49(2) . ? C3 C4 1.35(2) . ? C4 C5 1.36(2) . ? C5 C6 1.39(2) . ? C7 N1 1.473(19) . ? C8 N1 1.446(18) . ? C9 N1 1.437(18) . ? C10 C11 1.389(19) . ? C10 C15 1.390(19) . ? C10 Bi1 2.249(15) . ? C11 C12 1.386(19) . ? C11 C16 1.52(2) . ? C12 C13 1.40(2) . ? C13 C14 1.38(2) . ? C14 C15 1.415(19) . ? C16 N2 1.457(18) . ? C17 N2 1.448(17) . ? C18 N2 1.437(16) . ? O1 Bi1 2.124(9) . ? O1 Bi1 2.124(9) 2 ? Bi1 Bi1 3.4647(13) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.1(15) . . ? C6 C1 Bi1 118.9(11) . . ? C2 C1 Bi1 120.9(12) . . ? C1 C2 C3 117.4(17) . . ? C1 C2 C7 122.5(14) . . ? C3 C2 C7 120.0(15) . . ? C4 C3 C2 121.1(17) . . ? C3 C4 C5 122.6(17) . . ? C4 C5 C6 118.3(18) . . ? C5 C6 C1 120.6(16) . . ? N1 C7 C2 112.7(12) . . ? C11 C10 C15 118.8(14) . . ? C11 C10 Bi1 120.1(11) . . ? C15 C10 Bi1 121.0(10) . . ? C12 C11 C10 120.4(14) . . ? C12 C11 C16 119.3(14) . . ? C10 C11 C16 120.2(13) . . ? C11 C12 C13 120.5(15) . . ? C14 C13 C12 120.4(15) . . ? C13 C14 C15 118.2(14) . . ? C10 C15 C14 121.6(13) . . ? N2 C16 C11 112.0(12) . . ? C9 N1 C8 110.7(14) . . ? C9 N1 C7 110.0(12) . . ? C8 N1 C7 111.5(13) . . ? C18 N2 C17 108.9(11) . . ? C18 N2 C16 110.1(12) . . ? C17 N2 C16 111.0(12) . . ? Bi1 O1 Bi1 109.3(7) . 2 ? O1 Bi1 C10 95.7(4) . . ? O1 Bi1 C1 88.6(5) . . ? C10 Bi1 C1 93.9(5) . . ? O1 Bi1 Bi1 35.3(3) . 2 ? C10 Bi1 Bi1 114.6(3) . 2 ? C1 Bi1 Bi1 115.3(4) . 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 C6 C1 C2 C3 -1(2) . . . . ? Bi1 C1 C2 C3 174.4(11) . . . . ? C6 C1 C2 C7 175.8(14) . . . . ? Bi1 C1 C2 C7 -8.9(19) . . . . ? C1 C2 C3 C4 1(2) . . . . ? C7 C2 C3 C4 -176.2(16) . . . . ? C2 C3 C4 C5 1(3) . . . . ? C3 C4 C5 C6 -2(3) . . . . ? C4 C5 C6 C1 2(3) . . . . ? C2 C1 C6 C5 0(2) . . . . ? Bi1 C1 C6 C5 -175.9(12) . . . . ? C1 C2 C7 N1 37.0(19) . . . . ? C3 C2 C7 N1 -146.4(14) . . . . ? C15 C10 C11 C12 -1(2) . . . . ? Bi1 C10 C11 C12 176.6(10) . . . . ? C15 C10 C11 C16 175.8(13) . . . . ? Bi1 C10 C11 C16 -6.6(17) . . . . ? C10 C11 C12 C13 0(2) . . . . ? C16 C11 C12 C13 -177.2(13) . . . . ? C11 C12 C13 C14 0(2) . . . . ? C12 C13 C14 C15 2(2) . . . . ? C11 C10 C15 C14 3(2) . . . . ? Bi1 C10 C15 C14 -174.9(10) . . . . ? C13 C14 C15 C10 -3(2) . . . . ? C12 C11 C16 N2 122.0(14) . . . . ? C10 C11 C16 N2 -54.8(17) . . . . ? C2 C7 N1 C9 73.1(15) . . . . ? C2 C7 N1 C8 -163.8(12) . . . . ? C11 C16 N2 C18 -67.0(15) . . . . ? C11 C16 N2 C17 172.3(11) . . . . ? Bi1 O1 Bi1 C10 -125.6(4) 2 . . . ? Bi1 O1 Bi1 C1 140.6(3) 2 . . . ? C11 C10 Bi1 O1 109.6(11) . . . . ? C15 C10 Bi1 O1 -72.9(12) . . . . ? C11 C10 Bi1 C1 -161.4(11) . . . . ? C15 C10 Bi1 C1 16.1(12) . . . . ? C11 C10 Bi1 Bi1 78.4(11) . . . 2 ? C15 C10 Bi1 Bi1 -104.1(11) . . . 2 ? C6 C1 Bi1 O1 -19.4(11) . . . . ? C2 C1 Bi1 O1 165.2(11) . . . . ? C6 C1 Bi1 C10 -115.1(12) . . . . ? C2 C1 Bi1 C10 69.6(12) . . . . ? C6 C1 Bi1 Bi1 4.5(13) . . . 2 ? C2 C1 Bi1 Bi1 -170.8(10) . . . 2 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.230 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.208 # Attachment 'Compound 3-C6H6 - CCDC 658671.cif' data_rw12 _database_code_depnum_ccdc_archive 'CCDC 658671' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H48 Bi2 N4 O3, C6 H6' _chemical_formula_sum 'C43 H54 Bi2 N4 O3' _chemical_formula_weight 1092.86 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.902(2) _cell_length_b 14.011(2) _cell_length_c 14.107(4) _cell_angle_alpha 99.170(10) _cell_angle_beta 92.64(2) _cell_angle_gamma 109.550(10) _cell_volume 2541.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 2.952 _cell_measurement_theta_max 12.655 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 6.949 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min 0.1030 _exptl_absorpt_correction_T_max 0.1676 _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst A, 1983' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 13112 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 11503 _reflns_number_gt 8614 _reflns_threshold_expression >2\s(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, Crystal Impact' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; One melecule of C6H6 is disordered over two positions, SOF 0.5 each. The high adp's are indicating an additional disordering. A further treatment does not lead to significant better results. The 1,2- and 1,3-distances of these two moities were restrained to be equal by SADI commands. The void of 99 A^3 which was reported by iucr's checkcif/Platon contains only 1 electron # SQUEEZE RESULTS (APPEND TO CIF) #loop_ #_platon_squeeze_void_nr #_platon_squeeze_void_average_x #_platon_squeeze_void_average_y #_platon_squeeze_void_average_z #_platon_squeeze_void_volume #_platon_squeeze_void_count_electrons 1 0.000 0.000 0.500 25.0 -3.3 2 -0.043 0.230 0.441 23.7 -0.6 3 0.019 0.391 0.545 11.1 0.0 4 -0.019 0.622 0.470 12.6 0.9 5 0.051 0.782 0.563 22.0 -1.2 6 0.134 0.775 0.799 11.5 -0.2 7 0.500 0.000 1.000 100.2 -1.2 8 0.866 0.225 0.202 11.7 0.1 A refinement suggested by "Platon/Squeeze" (removing the disordered solvent) shows a void of almost 900 A^3 with 24 electrons. # SQUEEZE RESULTS (APPEND TO CIF) #loop_ #_platon_squeeze_void_nr #_platon_squeeze_void_average_x #_platon_squeeze_void_average_y #_platon_squeeze_void_average_z #_platon_squeeze_void_volume #_platon_squeeze_void_count_electrons 1 -0.003 0.000 -0.002 885.8 24.2 #_platon_squeeze_details Refinement of this dataset leads to nearly the same results like the disordered model. 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^)+(0.0877P)^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 0.0030(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11503 _refine_ls_number_parameters 532 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.032 _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 0.33246(2) 0.57092(2) 0.143542(19) 0.03038(10) Uani 1 1 d . . . Bi2 Bi 0.43750(2) 0.81813(2) 0.529515(19) 0.03230(10) Uani 1 1 d . . . C37 C 0.4319(6) 0.7178(6) 0.3242(6) 0.0326(16) Uani 1 1 d . . . O1 O 0.3511(5) 0.6604(4) 0.3484(4) 0.0400(12) Uani 1 1 d . . . O2 O 0.4525(4) 0.7095(4) 0.2362(4) 0.0400(13) Uani 1 1 d . . . O3 O 0.4996(4) 0.7902(4) 0.3864(4) 0.0358(12) Uani 1 1 d . . . C1 C 0.4296(5) 0.6218(6) 0.0246(5) 0.0331(16) Uani 1 1 d . . . C2 C 0.5011(7) 0.7214(6) 0.0324(6) 0.0411(18) Uani 1 1 d . . . H2 H 0.5088 0.7712 0.0891 0.049 Uiso 1 1 calc R . . C3 C 0.5613(7) 0.7485(8) -0.0425(7) 0.050(2) Uani 1 1 d . . . H3 H 0.6095 0.8162 -0.0373 0.061 Uiso 1 1 calc R . . C4 C 0.5489(7) 0.6733(8) -0.1258(7) 0.052(2) Uani 1 1 d . . . H4 H 0.5896 0.6895 -0.1773 0.062 Uiso 1 1 calc R . . C5 C 0.4765(7) 0.5748(7) -0.1322(6) 0.045(2) Uani 1 1 d . . . H5 H 0.4679 0.5244 -0.1886 0.054 Uiso 1 1 calc R . . C6 C 0.4177(6) 0.5498(6) -0.0590(6) 0.0351(16) Uani 1 1 d . . . C7 C 0.3466(6) 0.4444(7) -0.0663(6) 0.0414(19) Uani 1 1 d . . . H7A H 0.3810 0.4047 -0.0344 0.050 Uiso 1 1 calc R . . H7B H 0.3285 0.4114 -0.1353 0.050 Uiso 1 1 calc R . . N1 N 0.2515(5) 0.4404(5) -0.0217(5) 0.0410(16) Uani 1 1 d . . . C8 C 0.1870(7) 0.4758(8) -0.0853(7) 0.056(2) Uani 1 1 d . . . H8A H 0.2259 0.5457 -0.0944 0.083 Uiso 1 1 calc R . . H8B H 0.1248 0.4758 -0.0553 0.083 Uiso 1 1 calc R . . H8C H 0.1678 0.4292 -0.1481 0.083 Uiso 1 1 calc R . . C9 C 0.1956(7) 0.3372(6) -0.0010(7) 0.049(2) Uani 1 1 d . . . H9A H 0.1728 0.2872 -0.0617 0.073 Uiso 1 1 calc R . . H9B H 0.1358 0.3392 0.0323 0.073 Uiso 1 1 calc R . . H9C H 0.2412 0.3168 0.0401 0.073 Uiso 1 1 calc R . . C10 C 0.2288(6) 0.6608(6) 0.1176(6) 0.0369(17) Uani 1 1 d . . . C11 C 0.2511(7) 0.7298(7) 0.0535(7) 0.049(2) Uani 1 1 d . . . H11 H 0.3096 0.7369 0.0191 0.059 Uiso 1 1 calc R . . C12 C 0.1909(9) 0.7881(8) 0.0384(8) 0.063(3) Uani 1 1 d . . . H12 H 0.2074 0.8339 -0.0061 0.076 Uiso 1 1 calc R . . C13 C 0.1081(8) 0.7790(7) 0.0878(8) 0.059(3) Uani 1 1 d . . . H13 H 0.0663 0.8188 0.0777 0.071 Uiso 1 1 calc R . . C14 C 0.0833(6) 0.7121(7) 0.1534(7) 0.052(2) Uani 1 1 d . . . H14 H 0.0256 0.7071 0.1884 0.062 Uiso 1 1 calc R . . C15 C 0.1441(6) 0.6521(6) 0.1674(7) 0.0425(19) Uani 1 1 d . . . C16 C 0.1219(7) 0.5865(7) 0.2459(6) 0.047(2) Uani 1 1 d . . . H16A H 0.1790 0.6153 0.2985 0.056 Uiso 1 1 calc R . . H16B H 0.0585 0.5894 0.2734 0.056 Uiso 1 1 calc R . . N2 N 0.1093(5) 0.4790(6) 0.2086(5) 0.0443(17) Uani 1 1 d . . . C17 C 0.1208(8) 0.4266(8) 0.2865(8) 0.060(3) Uani 1 1 d . . . H17A H 0.1835 0.4682 0.3290 0.091 Uiso 1 1 calc R . . H17B H 0.1252 0.3594 0.2598 0.091 Uiso 1 1 calc R . . H17C H 0.0614 0.4167 0.3236 0.091 Uiso 1 1 calc R . . C18 C 0.0124(7) 0.4240(7) 0.1523(8) 0.058(3) Uani 1 1 d . . . H18A H -0.0431 0.4289 0.1910 0.087 Uiso 1 1 calc R . . H18B H 0.0053 0.3515 0.1328 0.087 Uiso 1 1 calc R . . H18C H 0.0087 0.4541 0.0947 0.087 Uiso 1 1 calc R . . C19 C 0.5900(6) 0.9515(5) 0.5676(5) 0.0345(16) Uani 1 1 d . . . C20 C 0.6707(6) 0.9615(7) 0.5142(6) 0.0421(19) Uani 1 1 d . . . H20 H 0.6658 0.9107 0.4592 0.051 Uiso 1 1 calc R . . C21 C 0.7593(7) 1.0456(7) 0.5403(7) 0.048(2) Uani 1 1 d . . . H21 H 0.8151 1.0534 0.5023 0.058 Uiso 1 1 calc R . . C22 C 0.7677(7) 1.1192(7) 0.6219(7) 0.055(2) Uani 1 1 d . . . H22 H 0.8286 1.1777 0.6397 0.067 Uiso 1 1 calc R . . C23 C 0.6885(7) 1.1062(7) 0.6748(7) 0.052(2) Uani 1 1 d . . . H23 H 0.6953 1.1553 0.7319 0.063 Uiso 1 1 calc R . . C24 C 0.5975(7) 1.0243(6) 0.6498(6) 0.0398(18) Uani 1 1 d . . . C25 C 0.5065(7) 1.0178(6) 0.7048(6) 0.046(2) Uani 1 1 d . . . H25A H 0.5303 1.0574 0.7713 0.055 Uiso 1 1 calc R . . H25B H 0.4626 1.0492 0.6734 0.055 Uiso 1 1 calc R . . N3 N 0.4463(6) 0.9113(5) 0.7088(5) 0.0431(16) Uani 1 1 d . . . C26 C 0.3425(8) 0.9031(8) 0.7333(8) 0.061(3) Uani 1 1 d . . . H26A H 0.3013 0.8305 0.7305 0.091 Uiso 1 1 calc R . . H26B H 0.3103 0.9316 0.6871 0.091 Uiso 1 1 calc R . . H26C H 0.3469 0.9417 0.7986 0.091 Uiso 1 1 calc R . . C27 C 0.4957(9) 0.8723(8) 0.7799(7) 0.059(3) Uani 1 1 d . . . H27A H 0.5640 0.8756 0.7625 0.089 Uiso 1 1 calc R . . H27B H 0.4540 0.8006 0.7809 0.089 Uiso 1 1 calc R . . H27C H 0.5022 0.9144 0.8440 0.089 Uiso 1 1 calc R . . C28 C 0.4999(6) 0.7025(6) 0.5807(6) 0.0376(17) Uani 1 1 d . . . C29 C 0.6051(7) 0.7259(7) 0.6018(6) 0.0421(19) Uani 1 1 d . . . H29 H 0.6514 0.7924 0.5981 0.051 Uiso 1 1 calc R . . C30 C 0.6423(7) 0.6531(7) 0.6280(6) 0.046(2) Uani 1 1 d . . . H30 H 0.7140 0.6699 0.6431 0.056 Uiso 1 1 calc R . . C31 C 0.5767(8) 0.5571(7) 0.6324(6) 0.049(2) Uani 1 1 d . . . H31 H 0.6029 0.5071 0.6499 0.058 Uiso 1 1 calc R . . C32 C 0.4720(8) 0.5322(7) 0.6114(6) 0.049(2) Uani 1 1 d . . . H32 H 0.4263 0.4655 0.6154 0.058 Uiso 1 1 calc R . . C33 C 0.4336(7) 0.6055(6) 0.5842(6) 0.0416(19) Uani 1 1 d . . . C34 C 0.3191(7) 0.5748(7) 0.5544(6) 0.047(2) Uani 1 1 d . . . H34A H 0.3087 0.5825 0.4865 0.056 Uiso 1 1 calc R . . H34B H 0.2849 0.5013 0.5579 0.056 Uiso 1 1 calc R . . N4 N 0.2712(6) 0.6368(6) 0.6152(6) 0.0491(18) Uani 1 1 d . . . C35 C 0.2565(8) 0.6059(9) 0.7090(7) 0.063(3) Uani 1 1 d . . . H35A H 0.2087 0.5347 0.7001 0.094 Uiso 1 1 calc R . . H35B H 0.2285 0.6516 0.7494 0.094 Uiso 1 1 calc R . . H35C H 0.3227 0.6105 0.7406 0.094 Uiso 1 1 calc R . . C36 C 0.1721(8) 0.6272(11) 0.5715(10) 0.082(4) Uani 1 1 d . . . H36A H 0.1803 0.6570 0.5127 0.123 Uiso 1 1 calc R . . H36B H 0.1394 0.6639 0.6169 0.123 Uiso 1 1 calc R . . H36C H 0.1291 0.5542 0.5549 0.123 Uiso 1 1 calc R . . C38 C 0.0320(17) 0.1219(16) 0.1474(18) 0.075(8) Uani 0.50 1 d PD . . H38 H -0.0170 0.1443 0.1173 0.090 Uiso 0.50 1 calc PR . . C39 C 0.097(2) 0.0936(19) 0.0968(12) 0.124(17) Uani 0.50 1 d PD . . H39 H 0.0902 0.0876 0.0286 0.149 Uiso 0.50 1 calc PR . . C40 C 0.1705(15) 0.0735(15) 0.140(2) 0.100(11) Uani 0.50 1 d PD . . H40 H 0.2234 0.0620 0.1043 0.120 Uiso 0.50 1 calc PR . . C41 C 0.1718(16) 0.0693(15) 0.231(2) 0.084(10) Uani 0.50 1 d PD . . H41 H 0.2203 0.0460 0.2607 0.101 Uiso 0.50 1 calc PR . . C42 C 0.1067(19) 0.0970(17) 0.2814(13) 0.091(11) Uani 0.50 1 d PD . . H42 H 0.1119 0.1009 0.3494 0.110 Uiso 0.50 1 calc PR . . C43 C 0.0344(17) 0.1195(14) 0.2390(18) 0.139(14) Uani 0.50 1 d PDU . . H43 H -0.0167 0.1342 0.2749 0.167 Uiso 0.50 1 calc PR . . C44 C 0.1108(15) 0.1475(17) 0.7320(17) 0.099(13) Uani 0.50 1 d PD A 1 H44 H 0.0638 0.1087 0.7703 0.118 Uiso 0.50 1 calc PR A 1 C45 C 0.2082(17) 0.1641(14) 0.7484(14) 0.093(8) Uani 0.50 1 d PDU A 1 H45 H 0.2325 0.1373 0.7985 0.112 Uiso 0.50 1 calc PR A 1 C46 C 0.2723(11) 0.2174(17) 0.6965(19) 0.097(9) Uani 0.50 1 d PDU A 1 H46 H 0.3435 0.2290 0.7080 0.117 Uiso 0.50 1 calc PR A 1 C47 C 0.239(2) 0.2550(15) 0.6287(17) 0.130(19) Uani 0.50 1 d PD A 1 H47 H 0.2858 0.2913 0.5887 0.156 Uiso 0.50 1 calc PR A 1 C48 C 0.143(2) 0.2429(18) 0.6158(17) 0.16(2) Uani 0.50 1 d PD A 1 H48 H 0.1194 0.2771 0.5716 0.191 Uiso 0.50 1 calc PR A 1 C49 C 0.0777(14) 0.184(2) 0.663(2) 0.22(4) Uani 0.50 1 d PD A 1 H49 H 0.0061 0.1672 0.6480 0.269 Uiso 0.50 1 calc PR A 1 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 0.02847(16) 0.03246(16) 0.03045(16) 0.00482(11) 0.00316(11) 0.01133(12) Bi2 0.03372(17) 0.03203(16) 0.03259(17) 0.00582(11) 0.00278(12) 0.01343(12) C37 0.032(4) 0.029(3) 0.036(4) 0.004(3) 0.000(3) 0.010(3) O1 0.043(3) 0.038(3) 0.033(3) 0.002(2) 0.002(2) 0.010(3) O2 0.041(3) 0.045(3) 0.027(3) 0.001(2) 0.005(2) 0.007(3) O3 0.032(3) 0.040(3) 0.031(3) 0.003(2) 0.001(2) 0.009(2) C1 0.026(4) 0.039(4) 0.038(4) 0.013(3) 0.003(3) 0.014(3) C2 0.045(5) 0.041(4) 0.039(4) 0.011(3) 0.009(4) 0.015(4) C3 0.046(5) 0.055(5) 0.052(5) 0.022(4) 0.014(4) 0.013(4) C4 0.058(6) 0.069(6) 0.043(5) 0.027(5) 0.024(4) 0.031(5) C5 0.050(5) 0.064(6) 0.028(4) 0.010(4) -0.001(4) 0.028(5) C6 0.032(4) 0.042(4) 0.033(4) 0.009(3) 0.003(3) 0.015(3) C7 0.036(4) 0.051(5) 0.037(4) -0.003(4) -0.002(3) 0.022(4) N1 0.031(3) 0.047(4) 0.042(4) -0.003(3) -0.006(3) 0.017(3) C8 0.043(5) 0.088(7) 0.040(5) 0.006(5) -0.009(4) 0.032(5) C9 0.042(5) 0.028(4) 0.061(6) -0.007(4) -0.002(4) 0.000(4) C10 0.027(4) 0.036(4) 0.043(4) 0.000(3) -0.003(3) 0.008(3) C11 0.045(5) 0.047(5) 0.056(5) 0.012(4) 0.002(4) 0.014(4) C12 0.070(7) 0.056(6) 0.071(7) 0.013(5) -0.009(6) 0.034(6) C13 0.057(6) 0.044(5) 0.082(7) 0.002(5) -0.013(5) 0.033(5) C14 0.027(4) 0.052(5) 0.068(6) -0.007(5) -0.004(4) 0.012(4) C15 0.032(4) 0.036(4) 0.055(5) -0.007(4) 0.004(4) 0.013(3) C16 0.036(4) 0.055(5) 0.046(5) 0.001(4) 0.010(4) 0.015(4) N2 0.026(3) 0.057(4) 0.052(4) 0.012(4) 0.003(3) 0.015(3) C17 0.047(6) 0.063(6) 0.074(7) 0.025(5) 0.010(5) 0.017(5) C18 0.035(5) 0.048(5) 0.085(8) 0.005(5) 0.006(5) 0.009(4) C19 0.047(5) 0.027(3) 0.031(4) 0.003(3) -0.002(3) 0.017(3) C20 0.036(4) 0.042(4) 0.042(5) 0.004(4) -0.007(4) 0.009(4) C21 0.035(5) 0.046(5) 0.055(5) 0.003(4) 0.000(4) 0.007(4) C22 0.040(5) 0.050(5) 0.067(6) -0.001(5) -0.013(5) 0.011(4) C23 0.052(6) 0.042(5) 0.052(5) -0.004(4) -0.015(4) 0.010(4) C24 0.046(5) 0.031(4) 0.043(4) 0.003(3) -0.007(4) 0.018(4) C25 0.062(6) 0.042(4) 0.041(5) 0.008(4) 0.010(4) 0.028(4) N3 0.055(5) 0.041(4) 0.040(4) 0.011(3) 0.012(3) 0.024(3) C26 0.064(7) 0.063(6) 0.060(6) 0.017(5) 0.025(5) 0.024(5) C27 0.089(8) 0.059(6) 0.042(5) 0.011(4) 0.006(5) 0.040(6) C28 0.042(4) 0.039(4) 0.035(4) 0.010(3) 0.004(3) 0.016(4) C29 0.040(5) 0.043(4) 0.049(5) 0.015(4) 0.007(4) 0.019(4) C30 0.052(5) 0.060(6) 0.039(4) 0.013(4) 0.013(4) 0.033(5) C31 0.071(6) 0.052(5) 0.038(4) 0.014(4) 0.010(4) 0.038(5) C32 0.076(7) 0.042(5) 0.034(4) 0.011(4) 0.007(4) 0.027(5) C33 0.055(5) 0.042(4) 0.031(4) 0.011(3) 0.014(4) 0.019(4) C34 0.051(5) 0.046(5) 0.043(5) 0.018(4) 0.012(4) 0.011(4) N4 0.049(4) 0.052(4) 0.051(4) 0.017(4) 0.014(4) 0.020(4) C35 0.056(6) 0.078(7) 0.056(6) 0.021(5) 0.026(5) 0.020(5) C36 0.050(7) 0.105(10) 0.106(10) 0.039(8) 0.017(7) 0.036(7) C38 0.078(17) 0.037(11) 0.10(2) 0.013(13) -0.037(16) 0.011(11) C39 0.19(4) 0.053(17) 0.064(17) 0.010(13) -0.04(2) -0.04(2) C40 0.068(18) 0.032(11) 0.17(3) 0.002(17) 0.04(2) -0.018(11) C41 0.062(16) 0.031(10) 0.14(3) 0.034(14) -0.045(17) -0.012(10) C42 0.065(16) 0.034(12) 0.14(3) 0.027(14) -0.053(17) -0.022(11) C43 0.17(3) 0.012(9) 0.20(3) 0.016(14) 0.06(2) -0.031(13) C44 0.052(14) 0.050(13) 0.13(2) -0.057(14) 0.068(16) -0.041(12) C45 0.108(16) 0.045(10) 0.105(15) -0.054(10) 0.004(13) 0.031(11) C46 0.048(11) 0.068(13) 0.132(17) -0.066(12) 0.044(12) -0.003(9) C47 0.14(3) 0.043(13) 0.12(3) -0.058(16) 0.11(2) -0.057(17) C48 0.18(4) 0.09(3) 0.18(4) -0.10(3) -0.05(4) 0.06(3) C49 0.044(16) 0.13(4) 0.38(8) -0.21(5) 0.03(3) -0.005(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O2 2.256(5) . ? Bi1 C1 2.257(7) . ? Bi1 C10 2.260(8) . ? Bi1 N1 2.658(7) . ? Bi2 O3 2.260(5) . ? Bi2 C28 2.270(8) . ? Bi2 C19 2.280(8) . ? Bi2 N3 2.632(7) . ? C37 O1 1.243(10) . ? C37 O2 1.282(9) . ? C37 O3 1.299(9) . ? C1 C6 1.388(11) . ? C1 C2 1.401(11) . ? C2 C3 1.399(12) . ? C3 C4 1.410(14) . ? C4 C5 1.396(13) . ? C5 C6 1.364(11) . ? C6 C7 1.460(11) . ? C7 N1 1.479(10) . ? N1 C9 1.477(11) . ? N1 C8 1.491(10) . ? C10 C15 1.379(11) . ? C10 C11 1.398(11) . ? C11 C12 1.382(13) . ? C12 C13 1.354(15) . ? C13 C14 1.393(14) . ? C14 C15 1.405(12) . ? C15 C16 1.528(12) . ? C16 N2 1.463(11) . ? N2 C18 1.432(11) . ? N2 C17 1.447(12) . ? C19 C20 1.360(12) . ? C19 C24 1.393(11) . ? C20 C21 1.374(12) . ? C21 C22 1.389(13) . ? C22 C23 1.337(14) . ? C23 C24 1.379(12) . ? C24 C25 1.498(12) . ? C25 N3 1.458(11) . ? N3 C27 1.463(11) . ? N3 C26 1.469(12) . ? C28 C33 1.373(11) . ? C28 C29 1.394(11) . ? C29 C30 1.379(11) . ? C30 C31 1.362(13) . ? C31 C32 1.383(14) . ? C32 C33 1.401(11) . ? C33 C34 1.522(12) . ? C34 N4 1.462(12) . ? N4 C36 1.438(13) . ? N4 C35 1.459(11) . ? C38 C43 1.297(10) . ? C38 C39 1.297(10) . ? C39 C40 1.298(10) . ? C40 C41 1.298(10) . ? C41 C42 1.298(10) . ? C42 C43 1.298(10) . ? C44 C49 1.296(10) . ? C44 C45 1.297(10) . ? C45 C46 1.296(10) . ? C46 C47 1.297(10) . ? C47 C48 1.298(10) . ? C48 C49 1.297(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 O2 Bi1 C1 83.4(2) . . ? O2 Bi1 C10 92.7(2) . . ? C1 Bi1 C10 94.2(3) . . ? O2 Bi1 N1 153.7(2) . . ? C1 Bi1 N1 70.4(3) . . ? C10 Bi1 N1 90.5(2) . . ? O3 Bi2 C28 89.1(2) . . ? O3 Bi2 C19 83.7(2) . . ? C28 Bi2 C19 94.0(3) . . ? O3 Bi2 N3 154.8(2) . . ? C28 Bi2 N3 90.9(3) . . ? C19 Bi2 N3 71.2(3) . . ? O1 C37 O2 121.9(7) . . ? O1 C37 O3 121.8(7) . . ? O2 C37 O3 116.3(7) . . ? C37 O2 Bi1 110.3(5) . . ? C37 O3 Bi2 111.9(5) . . ? C6 C1 C2 119.4(7) . . ? C6 C1 Bi1 117.7(5) . . ? C2 C1 Bi1 122.9(6) . . ? C3 C2 C1 120.7(8) . . ? C2 C3 C4 118.7(8) . . ? C5 C4 C3 119.5(8) . . ? C6 C5 C4 121.2(8) . . ? C5 C6 C1 120.5(8) . . ? C5 C6 C7 119.4(8) . . ? C1 C6 C7 120.0(7) . . ? C6 C7 N1 112.4(7) . . ? C9 N1 C7 112.2(7) . . ? C9 N1 C8 112.3(7) . . ? C7 N1 C8 108.7(7) . . ? C9 N1 Bi1 109.3(5) . . ? C7 N1 Bi1 99.6(4) . . ? C8 N1 Bi1 114.0(5) . . ? C15 C10 C11 118.2(8) . . ? C15 C10 Bi1 120.9(6) . . ? C11 C10 Bi1 120.8(6) . . ? C12 C11 C10 122.1(10) . . ? C13 C12 C11 119.2(10) . . ? C12 C13 C14 120.9(9) . . ? C13 C14 C15 119.7(9) . . ? C10 C15 C14 120.0(9) . . ? C10 C15 C16 120.6(7) . . ? C14 C15 C16 119.0(8) . . ? N2 C16 C15 112.0(7) . . ? C18 N2 C17 109.6(8) . . ? C18 N2 C16 112.3(7) . . ? C17 N2 C16 110.8(8) . . ? C20 C19 C24 120.5(8) . . ? C20 C19 Bi2 123.1(6) . . ? C24 C19 Bi2 116.4(6) . . ? C19 C20 C21 119.8(8) . . ? C20 C21 C22 120.4(9) . . ? C23 C22 C21 118.8(9) . . ? C22 C23 C24 122.5(9) . . ? C23 C24 C19 118.0(9) . . ? C23 C24 C25 121.2(8) . . ? C19 C24 C25 120.7(8) . . ? N3 C25 C24 111.5(7) . . ? C25 N3 C27 111.1(8) . . ? C25 N3 C26 110.4(7) . . ? C27 N3 C26 109.4(8) . . ? C25 N3 Bi2 101.9(5) . . ? C27 N3 Bi2 113.8(5) . . ? C26 N3 Bi2 110.0(6) . . ? C33 C28 C29 119.5(8) . . ? C33 C28 Bi2 119.4(6) . . ? C29 C28 Bi2 121.0(6) . . ? C30 C29 C28 120.3(8) . . ? C31 C30 C29 120.3(9) . . ? C30 C31 C32 120.2(8) . . ? C31 C32 C33 119.8(9) . . ? C28 C33 C32 119.8(9) . . ? C28 C33 C34 120.9(7) . . ? C32 C33 C34 119.3(8) . . ? N4 C34 C33 112.8(7) . . ? C36 N4 C35 107.3(8) . . ? C36 N4 C34 111.8(9) . . ? C35 N4 C34 111.5(7) . . ? C43 C38 C39 119.9(3) . . ? C38 C39 C40 119.9(3) . . ? C41 C40 C39 119.8(3) . . ? C40 C41 C42 119.9(3) . . ? C43 C42 C41 120.0(3) . . ? C38 C43 C42 119.9(3) . . ? C49 C44 C45 120.0(3) . . ? C46 C45 C44 119.9(3) . . ? C45 C46 C47 120.1(3) . . ? C46 C47 C48 119.9(3) . . ? C49 C48 C47 119.7(3) . . ? C44 C49 C48 119.9(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 O1 C37 O2 Bi1 -5.9(9) . . . . ? O3 C37 O2 Bi1 174.9(5) . . . . ? C1 Bi1 O2 C37 -179.5(5) . . . . ? C10 Bi1 O2 C37 86.6(5) . . . . ? N1 Bi1 O2 C37 -177.0(5) . . . . ? O1 C37 O3 Bi2 -12.1(9) . . . . ? O2 C37 O3 Bi2 167.2(5) . . . . ? C28 Bi2 O3 C37 91.8(5) . . . . ? C19 Bi2 O3 C37 -174.1(5) . . . . ? N3 Bi2 O3 C37 -178.0(5) . . . . ? O2 Bi1 C1 C6 160.7(6) . . . . ? C10 Bi1 C1 C6 -107.1(6) . . . . ? N1 Bi1 C1 C6 -18.1(5) . . . . ? O2 Bi1 C1 C2 -18.7(6) . . . . ? C10 Bi1 C1 C2 73.6(6) . . . . ? N1 Bi1 C1 C2 162.6(7) . . . . ? C6 C1 C2 C3 -0.9(12) . . . . ? Bi1 C1 C2 C3 178.5(6) . . . . ? C1 C2 C3 C4 -0.3(13) . . . . ? C2 C3 C4 C5 0.9(14) . . . . ? C3 C4 C5 C6 -0.4(13) . . . . ? C4 C5 C6 C1 -0.8(12) . . . . ? C4 C5 C6 C7 -176.8(8) . . . . ? C2 C1 C6 C5 1.5(11) . . . . ? Bi1 C1 C6 C5 -177.9(6) . . . . ? C2 C1 C6 C7 177.4(7) . . . . ? Bi1 C1 C6 C7 -2.0(9) . . . . ? C5 C6 C7 N1 -145.3(7) . . . . ? C1 C6 C7 N1 38.7(10) . . . . ? C6 C7 N1 C9 -161.7(7) . . . . ? C6 C7 N1 C8 73.4(9) . . . . ? C6 C7 N1 Bi1 -46.2(7) . . . . ? O2 Bi1 N1 C9 148.5(6) . . . . ? C1 Bi1 N1 C9 151.2(6) . . . . ? C10 Bi1 N1 C9 -114.5(5) . . . . ? O2 Bi1 N1 C7 30.8(8) . . . . ? C1 Bi1 N1 C7 33.5(5) . . . . ? C10 Bi1 N1 C7 127.8(5) . . . . ? O2 Bi1 N1 C8 -84.8(7) . . . . ? C1 Bi1 N1 C8 -82.1(6) . . . . ? C10 Bi1 N1 C8 12.2(6) . . . . ? O2 Bi1 C10 C15 -101.9(6) . . . . ? C1 Bi1 C10 C15 174.6(6) . . . . ? N1 Bi1 C10 C15 104.2(6) . . . . ? O2 Bi1 C10 C11 75.5(7) . . . . ? C1 Bi1 C10 C11 -8.0(7) . . . . ? N1 Bi1 C10 C11 -78.4(7) . . . . ? C15 C10 C11 C12 -0.5(13) . . . . ? Bi1 C10 C11 C12 -178.0(7) . . . . ? C10 C11 C12 C13 0.6(16) . . . . ? C11 C12 C13 C14 0.1(16) . . . . ? C12 C13 C14 C15 -0.9(15) . . . . ? C11 C10 C15 C14 -0.3(12) . . . . ? Bi1 C10 C15 C14 177.2(6) . . . . ? C11 C10 C15 C16 -173.8(8) . . . . ? Bi1 C10 C15 C16 3.7(10) . . . . ? C13 C14 C15 C10 1.0(13) . . . . ? C13 C14 C15 C16 174.6(8) . . . . ? C10 C15 C16 N2 -58.9(10) . . . . ? C14 C15 C16 N2 127.6(8) . . . . ? C15 C16 N2 C18 -75.1(9) . . . . ? C15 C16 N2 C17 161.9(7) . . . . ? O3 Bi2 C19 C20 -13.6(6) . . . . ? C28 Bi2 C19 C20 75.0(7) . . . . ? N3 Bi2 C19 C20 164.6(7) . . . . ? O3 Bi2 C19 C24 166.3(6) . . . . ? C28 Bi2 C19 C24 -105.1(6) . . . . ? N3 Bi2 C19 C24 -15.5(5) . . . . ? C24 C19 C20 C21 -1.7(12) . . . . ? Bi2 C19 C20 C21 178.2(6) . . . . ? C19 C20 C21 C22 1.3(14) . . . . ? C20 C21 C22 C23 0.6(14) . . . . ? C21 C22 C23 C24 -2.2(15) . . . . ? C22 C23 C24 C19 1.9(13) . . . . ? C22 C23 C24 C25 -173.6(9) . . . . ? C20 C19 C24 C23 0.1(11) . . . . ? Bi2 C19 C24 C23 -179.8(6) . . . . ? C20 C19 C24 C25 175.6(7) . . . . ? Bi2 C19 C24 C25 -4.3(9) . . . . ? C23 C24 C25 N3 -146.4(8) . . . . ? C19 C24 C25 N3 38.3(11) . . . . ? C24 C25 N3 C27 77.1(9) . . . . ? C24 C25 N3 C26 -161.3(7) . . . . ? C24 C25 N3 Bi2 -44.5(7) . . . . ? O3 Bi2 N3 C25 36.4(8) . . . . ? C28 Bi2 N3 C25 126.2(5) . . . . ? C19 Bi2 N3 C25 32.3(5) . . . . ? O3 Bi2 N3 C27 -83.3(8) . . . . ? C28 Bi2 N3 C27 6.5(7) . . . . ? C19 Bi2 N3 C27 -87.4(7) . . . . ? O3 Bi2 N3 C26 153.5(6) . . . . ? C28 Bi2 N3 C26 -116.7(6) . . . . ? C19 Bi2 N3 C26 149.4(6) . . . . ? O3 Bi2 C28 C33 -103.6(6) . . . . ? C19 Bi2 C28 C33 172.8(7) . . . . ? N3 Bi2 C28 C33 101.6(7) . . . . ? O3 Bi2 C28 C29 71.6(7) . . . . ? C19 Bi2 C28 C29 -12.0(7) . . . . ? N3 Bi2 C28 C29 -83.2(7) . . . . ? C33 C28 C29 C30 -1.5(13) . . . . ? Bi2 C28 C29 C30 -176.6(6) . . . . ? C28 C29 C30 C31 0.8(13) . . . . ? C29 C30 C31 C32 -0.6(13) . . . . ? C30 C31 C32 C33 1.0(13) . . . . ? C29 C28 C33 C32 1.8(12) . . . . ? Bi2 C28 C33 C32 177.1(6) . . . . ? C29 C28 C33 C34 -175.4(8) . . . . ? Bi2 C28 C33 C34 -0.2(10) . . . . ? C31 C32 C33 C28 -1.6(13) . . . . ? C31 C32 C33 C34 175.7(8) . . . . ? C28 C33 C34 N4 -62.2(10) . . . . ? C32 C33 C34 N4 120.5(8) . . . . ? C33 C34 N4 C36 164.0(8) . . . . ? C33 C34 N4 C35 -75.8(9) . . . . ? C43 C38 C39 C40 -7(4) . . . . ? C38 C39 C40 C41 9(4) . . . . ? C39 C40 C41 C42 -8(3) . . . . ? C40 C41 C42 C43 7(3) . . . . ? C39 C38 C43 C42 6(4) . . . . ? C41 C42 C43 C38 -5(3) . . . . ? C49 C44 C45 C46 0(4) . . . . ? C44 C45 C46 C47 1(3) . . . . ? C45 C46 C47 C48 3(4) . . . . ? C46 C47 C48 C49 -7(4) . . . . ? C45 C44 C49 C48 -5(5) . . . . ? C47 C48 C49 C44 8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.712 _refine_diff_density_min -1.946 _refine_diff_density_rms 0.202 # Attachment 'Compound 4 - CCDC 658672.cif' #=========================================================================== data_n1 _database_code_depnum_ccdc_archive 'CCDC 658672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H48 Bi2 N4 S' _chemical_formula_sum 'C36 H48 Bi2 N4 S' _chemical_formula_weight 986.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.939(3) _cell_length_b 7.3660(10) _cell_length_c 18.947(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.43(1) _cell_angle_gamma 90.00 _cell_volume 3604.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 31 _cell_measurement_theta_min 4.516 _cell_measurement_theta_max 25.444 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1896 _exptl_absorpt_coefficient_mu 9.839 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.0250 _exptl_absorpt_correction_T_max 0.3970 _exptl_absorpt_process_details 'Walker & Stuart, (1983) Acta Cryst. A' _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 9509 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4089 _reflns_number_gt 2962 _reflns_threshold_expression >2\s(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, Crystal Impact' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4089 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0661 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.569270(9) 0.38147(3) 0.327404(12) 0.02020(7) Uani 1 1 d . . . S1 S 0.5000 0.1542(3) 0.2500 0.0264(5) Uani 1 2 d S . . N1 N 0.6656(2) 0.5026(8) 0.4446(3) 0.0291(13) Uani 1 1 d . . . N2 N 0.5646(2) 0.5618(7) 0.1804(3) 0.0263(13) Uani 1 1 d . . . C1 C 0.5929(2) 0.1983(9) 0.4327(3) 0.0219(13) Uani 1 1 d . . . C2 C 0.6414(3) 0.2150(10) 0.4938(3) 0.0255(15) Uani 1 1 d . . . C3 C 0.6507(3) 0.1197(11) 0.5600(3) 0.0328(15) Uani 1 1 d . . . H3 H 0.6825 0.1338 0.6004 0.045(8) Uiso 1 1 calc R . . C4 C 0.6147(3) 0.0039(11) 0.5685(4) 0.0329(17) Uani 1 1 d . . . H4 H 0.6222 -0.0608 0.6137 0.045(8) Uiso 1 1 calc R . . C5 C 0.5670(3) -0.0152(10) 0.5092(4) 0.0306(16) Uani 1 1 d . . . H5 H 0.5422 -0.0930 0.5139 0.045(8) Uiso 1 1 calc R . . C6 C 0.5568(2) 0.0840(9) 0.4423(4) 0.0258(15) Uani 1 1 d . . . H6 H 0.5245 0.0727 0.4029 0.045(8) Uiso 1 1 calc R . . C7 C 0.6835(3) 0.3288(10) 0.4859(4) 0.0304(16) Uani 1 1 d . . . H7A H 0.7088 0.3553 0.5365 0.043(11) Uiso 1 1 calc R . . H7B H 0.7007 0.2585 0.4592 0.043(11) Uiso 1 1 calc R . . C8 C 0.7057(3) 0.5798(10) 0.4225(4) 0.0377(19) Uani 1 1 d . . . H8A H 0.6941 0.6943 0.3977 0.047(7) Uiso 1 1 calc R . . H8B H 0.7128 0.4985 0.3881 0.047(7) Uiso 1 1 calc R . . H8C H 0.7366 0.5976 0.4671 0.047(7) Uiso 1 1 calc R . . C9 C 0.6500(3) 0.6308(12) 0.4909(4) 0.0397(17) Uani 1 1 d . . . H9A H 0.6800 0.6708 0.5333 0.047(7) Uiso 1 1 calc R . . H9B H 0.6264 0.5722 0.5095 0.047(7) Uiso 1 1 calc R . . H9C H 0.6332 0.7335 0.4602 0.047(7) Uiso 1 1 calc R . . C10 C 0.6300(2) 0.2764(9) 0.2858(3) 0.0207(13) Uani 1 1 d . . . C11 C 0.6456(2) 0.3889(10) 0.2391(3) 0.0238(13) Uani 1 1 d . . . C12 C 0.6855(2) 0.3326(10) 0.2175(4) 0.0298(16) Uani 1 1 d . . . H12 H 0.6961 0.4079 0.1868 0.045(8) Uiso 1 1 calc R . . C13 C 0.7097(3) 0.1683(11) 0.2406(4) 0.0331(17) Uani 1 1 d . . . H13 H 0.7363 0.1332 0.2255 0.045(8) Uiso 1 1 calc R . . C14 C 0.6942(3) 0.0546(11) 0.2864(4) 0.0323(16) Uani 1 1 d . . . H14 H 0.7105 -0.0565 0.3026 0.045(8) Uiso 1 1 calc R . . C15 C 0.6539(2) 0.1099(11) 0.3078(3) 0.0267(14) Uani 1 1 d . . . H15 H 0.6428 0.0331 0.3375 0.045(8) Uiso 1 1 calc R . . C16 C 0.6209(3) 0.5722(9) 0.2153(4) 0.0298(16) Uani 1 1 d . . . H16A H 0.6309 0.6507 0.2597 0.043(11) Uiso 1 1 calc R . . H16B H 0.6338 0.6261 0.1792 0.043(11) Uiso 1 1 calc R . . C17 C 0.5474(3) 0.4782(13) 0.1059(4) 0.043(2) Uani 1 1 d . . . H17A H 0.5604 0.5461 0.0737 0.047(7) Uiso 1 1 calc R . . H17B H 0.5102 0.4771 0.0837 0.047(7) Uiso 1 1 calc R . . H17C H 0.5601 0.3559 0.1108 0.047(7) Uiso 1 1 calc R . . C18 C 0.5414(3) 0.7449(11) 0.1762(5) 0.045(2) Uani 1 1 d . . . H18A H 0.5487 0.7894 0.2269 0.047(7) Uiso 1 1 calc R . . H18B H 0.5046 0.7374 0.1490 0.047(7) Uiso 1 1 calc R . . H18C H 0.5558 0.8263 0.1500 0.047(7) 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 0.01926(11) 0.02032(11) 0.02119(10) -0.00042(13) 0.00790(8) 0.00109(14) S1 0.0224(11) 0.0239(14) 0.0277(11) 0.000 0.0036(9) 0.000 N1 0.028(3) 0.031(3) 0.028(3) -0.007(3) 0.009(2) -0.008(3) N2 0.034(3) 0.018(3) 0.031(3) 0.007(2) 0.017(3) 0.007(2) C1 0.026(3) 0.019(3) 0.021(3) 0.002(3) 0.010(3) 0.002(3) C2 0.025(3) 0.028(4) 0.023(3) -0.004(3) 0.008(3) 0.001(3) C3 0.035(4) 0.035(4) 0.020(3) 0.000(4) 0.002(3) 0.015(4) C4 0.042(4) 0.036(4) 0.023(3) 0.004(3) 0.014(3) 0.009(4) C5 0.035(4) 0.029(4) 0.034(4) 0.002(3) 0.020(3) 0.000(3) C6 0.022(3) 0.026(4) 0.028(3) 0.001(3) 0.009(3) 0.003(3) C7 0.021(3) 0.036(4) 0.031(3) -0.003(3) 0.006(3) 0.005(3) C8 0.040(4) 0.034(5) 0.041(4) -0.004(3) 0.018(3) -0.010(4) C9 0.051(4) 0.031(4) 0.040(4) -0.004(4) 0.020(3) 0.002(5) C10 0.020(3) 0.017(3) 0.023(3) 0.001(3) 0.004(2) 0.004(3) C11 0.026(3) 0.020(3) 0.025(3) -0.002(3) 0.008(2) 0.000(3) C12 0.025(3) 0.037(5) 0.030(3) -0.006(3) 0.014(3) -0.007(3) C13 0.026(3) 0.042(5) 0.033(3) -0.007(3) 0.013(3) 0.000(3) C14 0.024(4) 0.029(4) 0.039(4) -0.008(3) 0.006(3) 0.005(3) C15 0.026(3) 0.027(4) 0.026(3) 0.003(3) 0.009(3) -0.004(4) C16 0.039(4) 0.021(4) 0.034(4) 0.005(3) 0.019(3) -0.002(3) C17 0.042(5) 0.060(6) 0.027(4) 0.000(4) 0.013(3) 0.005(4) C18 0.043(5) 0.025(4) 0.077(6) 0.013(4) 0.035(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C10 2.262(6) . ? Bi1 C1 2.287(6) . ? Bi1 S1 2.5558(17) . ? S1 Bi1 2.5558(16) 2_655 ? N1 C8 1.452(8) . ? N1 C9 1.465(9) . ? N1 C7 1.484(9) . ? N2 C17 1.444(9) . ? N2 C16 1.457(9) . ? N2 C18 1.486(9) . ? C1 C6 1.380(9) . ? C1 C2 1.411(9) . ? C2 C3 1.374(9) . ? C2 C7 1.497(9) . ? C3 C4 1.376(10) . ? C4 C5 1.383(10) . ? C5 C6 1.395(9) . ? C10 C15 1.382(9) . ? C10 C11 1.399(9) . ? C11 C12 1.388(9) . ? C11 C16 1.505(9) . ? C12 C13 1.374(10) . ? C13 C14 1.388(10) . ? C14 C15 1.396(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Bi1 C1 95.5(2) . . ? C10 Bi1 S1 94.60(16) . . ? C1 Bi1 S1 91.02(17) . . ? Bi1 S1 Bi1 98.17(8) . 2_655 ? C8 N1 C9 111.0(6) . . ? C8 N1 C7 110.5(6) . . ? C9 N1 C7 110.9(5) . . ? C17 N2 C16 111.4(5) . . ? C17 N2 C18 111.0(6) . . ? C16 N2 C18 110.5(6) . . ? C6 C1 C2 117.8(6) . . ? C6 C1 Bi1 119.5(5) . . ? C2 C1 Bi1 122.1(5) . . ? C3 C2 C1 119.6(6) . . ? C3 C2 C7 119.7(6) . . ? C1 C2 C7 120.7(6) . . ? C2 C3 C4 122.1(6) . . ? C3 C4 C5 119.3(6) . . ? C4 C5 C6 119.0(7) . . ? C1 C6 C5 122.2(6) . . ? N1 C7 C2 114.7(5) . . ? C15 C10 C11 119.0(6) . . ? C15 C10 Bi1 122.6(4) . . ? C11 C10 Bi1 118.3(5) . . ? C12 C11 C10 119.2(7) . . ? C12 C11 C16 120.5(6) . . ? C10 C11 C16 120.2(5) . . ? C13 C12 C11 121.4(7) . . ? C12 C13 C14 119.9(6) . . ? C13 C14 C15 118.9(7) . . ? C10 C15 C14 121.4(6) . . ? N2 C16 C11 112.4(6) . . ? 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 C10 Bi1 S1 Bi1 -121.60(15) . . . 2_655 ? C1 Bi1 S1 Bi1 142.76(15) . . . 2_655 ? C10 Bi1 C1 C6 -123.2(5) . . . . ? S1 Bi1 C1 C6 -28.5(5) . . . . ? C10 Bi1 C1 C2 65.7(5) . . . . ? S1 Bi1 C1 C2 160.4(5) . . . . ? C6 C1 C2 C3 -0.5(10) . . . . ? Bi1 C1 C2 C3 170.8(5) . . . . ? C6 C1 C2 C7 176.7(6) . . . . ? Bi1 C1 C2 C7 -12.0(9) . . . . ? C1 C2 C3 C4 1.5(11) . . . . ? C7 C2 C3 C4 -175.7(7) . . . . ? C2 C3 C4 C5 -1.2(11) . . . . ? C3 C4 C5 C6 -0.1(11) . . . . ? C2 C1 C6 C5 -0.9(10) . . . . ? Bi1 C1 C6 C5 -172.4(5) . . . . ? C4 C5 C6 C1 1.2(10) . . . . ? C8 N1 C7 C2 -165.2(6) . . . . ? C9 N1 C7 C2 71.2(7) . . . . ? C3 C2 C7 N1 -142.3(6) . . . . ? C1 C2 C7 N1 40.5(9) . . . . ? C1 Bi1 C10 C15 20.8(5) . . . . ? S1 Bi1 C10 C15 -70.7(5) . . . . ? C1 Bi1 C10 C11 -155.9(5) . . . . ? S1 Bi1 C10 C11 112.7(5) . . . . ? C15 C10 C11 C12 -1.5(9) . . . . ? Bi1 C10 C11 C12 175.3(5) . . . . ? C15 C10 C11 C16 -179.0(6) . . . . ? Bi1 C10 C11 C16 -2.2(8) . . . . ? C10 C11 C12 C13 0.5(10) . . . . ? C16 C11 C12 C13 178.0(6) . . . . ? C11 C12 C13 C14 0.0(10) . . . . ? C12 C13 C14 C15 0.4(10) . . . . ? C11 C10 C15 C14 2.0(9) . . . . ? Bi1 C10 C15 C14 -174.6(5) . . . . ? C13 C14 C15 C10 -1.5(10) . . . . ? C17 N2 C16 C11 -70.7(7) . . . . ? C18 N2 C16 C11 165.4(6) . . . . ? C12 C11 C16 N2 129.4(6) . . . . ? C10 C11 C16 N2 -53.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.219 _refine_diff_density_min -1.420 _refine_diff_density_rms 0.170 # Attachment 'Compound 6 - CCDC 658673.cif' data_rw14a _database_code_depnum_ccdc_archive 'CCDC 658673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Bi I N2' _chemical_formula_sum 'C18 H24 Bi I N2' _chemical_formula_weight 604.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.548(2) _cell_length_b 16.277(4) _cell_length_c 12.616(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.555(16) _cell_angle_gamma 90.00 _cell_volume 1959.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 5.39 _cell_measurement_theta_max 12.52 _exptl_crystal_description ? _exptl_crystal_colour yellow _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 2.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 10.570 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Stuart & Walker, Acta Cryst A, 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 10604 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4516 _reflns_number_gt 3849 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, Crystal Impact' _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^)+(0.0212P)^2^+0.8565P] 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 4516 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0603 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.413869(18) 0.647949(10) 0.563811(13) 0.02034(6) Uani 1 1 d . . . I1 I 0.23253(3) 0.586546(19) 0.74504(2) 0.02805(8) Uani 1 1 d . . . C1 C 0.3235(5) 0.5575(3) 0.4437(4) 0.0243(10) Uani 1 1 d . . . C2 C 0.2015(5) 0.5121(3) 0.4540(4) 0.0308(11) Uani 1 1 d . . . H2 H 0.1474 0.5184 0.5155 0.037 Uiso 1 1 calc R . . C3 C 0.1578(6) 0.4574(3) 0.3747(4) 0.0385(13) Uani 1 1 d . . . H3 H 0.0752 0.4258 0.3826 0.046 Uiso 1 1 calc R . . C4 C 0.2358(6) 0.4496(3) 0.2843(4) 0.0384(13) Uani 1 1 d . . . H4 H 0.2063 0.4127 0.2298 0.046 Uiso 1 1 calc R . . C5 C 0.3567(6) 0.4953(3) 0.2733(4) 0.0343(12) Uani 1 1 d . . . H5 H 0.4095 0.4899 0.2109 0.041 Uiso 1 1 calc R . . C6 C 0.4016(5) 0.5490(3) 0.3525(3) 0.0240(10) Uani 1 1 d . . . C7 C 0.5377(6) 0.5940(3) 0.3430(4) 0.0296(11) Uani 1 1 d . . . H7A H 0.6137 0.5608 0.3765 0.035 Uiso 1 1 calc R . . H7B H 0.5587 0.6004 0.2670 0.035 Uiso 1 1 calc R . . N1 N 0.5357(4) 0.6759(2) 0.3933(3) 0.0239(8) Uani 1 1 d . . . C8 C 0.6798(5) 0.7053(3) 0.4150(4) 0.0321(11) Uani 1 1 d . . . H8A H 0.7270 0.6684 0.4660 0.048 Uiso 1 1 calc R . . H8B H 0.6768 0.7609 0.4446 0.048 Uiso 1 1 calc R . . H8C H 0.7313 0.7060 0.3489 0.048 Uiso 1 1 calc R . . C9 C 0.4597(6) 0.7349(3) 0.3236(4) 0.0326(11) Uani 1 1 d . . . H9A H 0.4592 0.7891 0.3575 0.049 Uiso 1 1 calc R . . H9B H 0.3631 0.7161 0.3114 0.049 Uiso 1 1 calc R . . H9C H 0.5066 0.7387 0.2556 0.049 Uiso 1 1 calc R . . C10 C 0.2500(5) 0.7452(3) 0.5314(4) 0.0229(9) Uani 1 1 d . . . C11 C 0.1349(5) 0.7331(3) 0.4655(4) 0.0291(11) Uani 1 1 d . . . H11 H 0.1203 0.6812 0.4326 0.035 Uiso 1 1 calc R . . C12 C 0.0390(6) 0.7970(4) 0.4465(4) 0.0370(12) Uani 1 1 d . . . H12 H -0.0398 0.7883 0.4003 0.044 Uiso 1 1 calc R . . C13 C 0.0583(6) 0.8719(3) 0.4944(4) 0.0354(12) Uani 1 1 d . . . H13 H -0.0068 0.9152 0.4814 0.042 Uiso 1 1 calc R . . C14 C 0.1724(6) 0.8841(3) 0.5613(4) 0.0338(11) Uani 1 1 d . . . H14 H 0.1858 0.9361 0.5941 0.041 Uiso 1 1 calc R . . C15 C 0.2690(5) 0.8213(3) 0.5820(4) 0.0252(10) Uani 1 1 d . . . C16 C 0.3928(6) 0.8340(3) 0.6570(4) 0.0282(11) Uani 1 1 d . . . H16A H 0.3860 0.8888 0.6905 0.034 Uiso 1 1 calc R . . H16B H 0.3911 0.7921 0.7138 0.034 Uiso 1 1 calc R . . N2 N 0.5246(4) 0.8280(2) 0.6017(3) 0.0271(9) Uani 1 1 d . . . C17 C 0.5458(7) 0.9023(3) 0.5373(4) 0.0424(14) Uani 1 1 d . . . H17A H 0.5538 0.9504 0.5839 0.064 Uiso 1 1 calc R . . H17B H 0.4659 0.9095 0.4878 0.064 Uiso 1 1 calc R . . H17C H 0.6319 0.8965 0.4974 0.064 Uiso 1 1 calc R . . C18 C 0.6433(6) 0.8182(4) 0.6758(4) 0.0414(14) Uani 1 1 d . . . H18A H 0.6491 0.8659 0.7232 0.062 Uiso 1 1 calc R . . H18B H 0.7299 0.8138 0.6363 0.062 Uiso 1 1 calc R . . H18C H 0.6308 0.7682 0.7179 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01947(8) 0.02036(9) 0.02111(8) 0.00016(6) -0.00125(6) -0.00026(7) I1 0.03084(17) 0.02777(16) 0.02589(15) -0.00001(12) 0.00758(13) 0.00195(14) C1 0.026(2) 0.021(2) 0.026(2) -0.0030(18) -0.0021(19) 0.0055(19) C2 0.024(2) 0.034(3) 0.034(3) -0.002(2) -0.002(2) -0.004(2) C3 0.031(3) 0.037(3) 0.047(3) -0.005(2) -0.006(2) -0.008(2) C4 0.047(3) 0.029(3) 0.038(3) -0.009(2) -0.011(3) 0.003(3) C5 0.046(3) 0.031(3) 0.026(2) -0.008(2) 0.000(2) 0.007(3) C6 0.026(2) 0.023(2) 0.023(2) 0.0008(17) -0.0015(19) 0.006(2) C7 0.036(3) 0.024(2) 0.029(2) -0.0009(19) 0.011(2) 0.004(2) N1 0.0213(19) 0.0251(19) 0.025(2) 0.0021(16) 0.0032(17) -0.0020(17) C8 0.020(2) 0.039(3) 0.038(3) 0.003(2) 0.004(2) -0.004(2) C9 0.035(3) 0.033(3) 0.030(3) 0.007(2) -0.003(2) 0.002(2) C10 0.022(2) 0.023(2) 0.024(2) 0.0039(17) 0.0032(19) 0.0053(19) C11 0.026(2) 0.028(3) 0.034(3) -0.002(2) -0.001(2) 0.003(2) C12 0.023(2) 0.051(3) 0.036(3) 0.002(2) -0.005(2) 0.004(2) C13 0.035(3) 0.036(3) 0.035(3) 0.004(2) 0.003(2) 0.013(2) C14 0.044(3) 0.026(2) 0.031(3) -0.001(2) 0.008(2) 0.005(2) C15 0.030(3) 0.025(2) 0.021(2) -0.0002(18) 0.004(2) -0.001(2) C16 0.040(3) 0.019(2) 0.026(2) -0.0032(18) -0.001(2) -0.005(2) N2 0.032(2) 0.026(2) 0.0227(19) 0.0013(16) -0.0053(18) -0.0071(18) C17 0.060(4) 0.030(3) 0.036(3) 0.009(2) -0.003(3) -0.014(3) C18 0.041(3) 0.049(3) 0.033(3) 0.000(2) -0.011(3) -0.011(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 C10 2.256(4) . ? Bi1 C1 2.267(4) . ? Bi1 N1 2.514(4) . ? Bi1 I1 3.0723(6) . ? C1 C2 1.387(7) . ? C1 C6 1.395(6) . ? C2 C3 1.394(7) . ? C3 C4 1.384(8) . ? C4 C5 1.384(8) . ? C5 C6 1.386(7) . ? C6 C7 1.499(7) . ? C7 N1 1.477(6) . ? N1 C8 1.476(6) . ? N1 C9 1.480(6) . ? C10 C11 1.374(7) . ? C10 C15 1.402(6) . ? C11 C12 1.402(7) . ? C12 C13 1.372(8) . ? C13 C14 1.375(8) . ? C14 C15 1.396(7) . ? C15 C16 1.508(7) . ? C16 N2 1.458(7) . ? N2 C18 1.459(6) . ? N2 C17 1.474(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 Bi1 C1 94.90(16) . . ? C10 Bi1 N1 93.02(15) . . ? C1 Bi1 N1 73.86(15) . . ? C10 Bi1 I1 87.77(12) . . ? C1 Bi1 I1 94.25(12) . . ? N1 Bi1 I1 168.11(9) . . ? C2 C1 C6 119.6(4) . . ? C2 C1 Bi1 126.0(4) . . ? C6 C1 Bi1 114.4(3) . . ? C1 C2 C3 120.5(5) . . ? C4 C3 C2 119.5(5) . . ? C5 C4 C3 120.1(5) . . ? C4 C5 C6 120.7(5) . . ? C5 C6 C1 119.6(5) . . ? C5 C6 C7 120.1(4) . . ? C1 C6 C7 120.1(4) . . ? N1 C7 C6 112.6(4) . . ? C8 N1 C7 110.4(4) . . ? C8 N1 C9 109.8(4) . . ? C7 N1 C9 110.1(4) . . ? C8 N1 Bi1 110.5(3) . . ? C7 N1 Bi1 102.5(3) . . ? C9 N1 Bi1 113.3(3) . . ? C11 C10 C15 119.6(4) . . ? C11 C10 Bi1 123.2(3) . . ? C15 C10 Bi1 117.2(3) . . ? C10 C11 C12 120.3(5) . . ? C13 C12 C11 120.3(5) . . ? C12 C13 C14 119.5(5) . . ? C13 C14 C15 121.2(5) . . ? C14 C15 C10 119.0(5) . . ? C14 C15 C16 121.3(4) . . ? C10 C15 C16 119.8(4) . . ? N2 C16 C15 111.2(4) . . ? C16 N2 C18 111.5(4) . . ? C16 N2 C17 110.0(4) . . ? C18 N2 C17 109.1(4) . . ? 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 C10 Bi1 C1 C2 -72.7(4) . . . . ? N1 Bi1 C1 C2 -164.4(4) . . . . ? I1 Bi1 C1 C2 15.4(4) . . . . ? C10 Bi1 C1 C6 107.2(3) . . . . ? N1 Bi1 C1 C6 15.5(3) . . . . ? I1 Bi1 C1 C6 -164.7(3) . . . . ? C6 C1 C2 C3 0.9(7) . . . . ? Bi1 C1 C2 C3 -179.1(4) . . . . ? C1 C2 C3 C4 -1.1(8) . . . . ? C2 C3 C4 C5 0.4(8) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C4 C5 C6 C1 -0.5(7) . . . . ? C4 C5 C6 C7 175.9(5) . . . . ? C2 C1 C6 C5 -0.1(7) . . . . ? Bi1 C1 C6 C5 179.9(3) . . . . ? C2 C1 C6 C7 -176.5(4) . . . . ? Bi1 C1 C6 C7 3.6(5) . . . . ? C5 C6 C7 N1 148.2(4) . . . . ? C1 C6 C7 N1 -35.5(6) . . . . ? C6 C7 N1 C8 160.5(4) . . . . ? C6 C7 N1 C9 -78.1(5) . . . . ? C6 C7 N1 Bi1 42.7(4) . . . . ? C10 Bi1 N1 C8 117.1(3) . . . . ? C1 Bi1 N1 C8 -148.7(3) . . . . ? I1 Bi1 N1 C8 -149.3(4) . . . . ? C10 Bi1 N1 C7 -125.2(3) . . . . ? C1 Bi1 N1 C7 -31.0(3) . . . . ? I1 Bi1 N1 C7 -31.6(6) . . . . ? C10 Bi1 N1 C9 -6.6(3) . . . . ? C1 Bi1 N1 C9 87.6(3) . . . . ? I1 Bi1 N1 C9 86.9(5) . . . . ? C1 Bi1 C10 C11 6.3(4) . . . . ? N1 Bi1 C10 C11 80.4(4) . . . . ? I1 Bi1 C10 C11 -87.7(4) . . . . ? C1 Bi1 C10 C15 -173.7(4) . . . . ? N1 Bi1 C10 C15 -99.6(3) . . . . ? I1 Bi1 C10 C15 92.2(3) . . . . ? C15 C10 C11 C12 1.8(7) . . . . ? Bi1 C10 C11 C12 -178.3(4) . . . . ? C10 C11 C12 C13 -0.6(8) . . . . ? C11 C12 C13 C14 -0.1(8) . . . . ? C12 C13 C14 C15 -0.3(8) . . . . ? C13 C14 C15 C10 1.4(7) . . . . ? C13 C14 C15 C16 -178.8(5) . . . . ? C11 C10 C15 C14 -2.1(7) . . . . ? Bi1 C10 C15 C14 177.9(4) . . . . ? C11 C10 C15 C16 178.1(4) . . . . ? Bi1 C10 C15 C16 -1.9(6) . . . . ? C14 C15 C16 N2 -115.7(5) . . . . ? C10 C15 C16 N2 64.1(6) . . . . ? C15 C16 N2 C18 -164.8(4) . . . . ? C15 C16 N2 C17 74.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.644 _refine_diff_density_min -0.882 _refine_diff_density_rms 0.144 # Attachment 'Compound 7 - CCDC 658674.cif' data_rw16i _database_code_depnum_ccdc_archive 'CCDC 658674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Bi2 Cl4 N2' _chemical_formula_sum 'C18 H24 Bi2 Cl4 N2' _chemical_formula_weight 828.16 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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0380(18) _cell_length_b 8.1540(16) _cell_length_c 16.107(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.95(3) _cell_angle_gamma 90.00 _cell_volume 1165.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.975 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 15.543 _exptl_absorpt_correction_type refdelF _exptl_absorpt_correction_T_min 0.0896 _exptl_absorpt_correction_T_max 0.1471 _exptl_absorpt_process_details 'Walker & Stuart, Acta Cryst A, 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 'STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 13075 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2249 _reflns_number_gt 1969 _reflns_threshold_expression >2\s(I) _computing_data_collection 'STOE Expose' _computing_cell_refinement 'STOE Cell' _computing_data_reduction 'STOE Reduce' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond, Crystal Impact' _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^)+(0.0317P)^2^+2.5144P] 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 2249 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0670 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 0.26083(2) 0.03214(3) 0.458810(14) 0.02314(10) Uani 1 1 d . . . Cl1 Cl 0.02498(18) -0.1530(2) 0.41692(12) 0.0354(4) Uani 1 1 d . . . Cl2 Cl 0.53395(16) 0.2271(2) 0.49172(10) 0.0297(3) Uani 1 1 d . . . C1 C 0.3076(6) 0.0004(8) 0.3291(4) 0.0242(13) Uani 1 1 d . . . C2 C 0.3530(6) -0.1431(8) 0.2969(4) 0.0278(14) Uani 1 1 d . . . H2 H 0.3696 -0.2379 0.3317 0.033 Uiso 1 1 calc R . . C3 C 0.3746(7) -0.1510(9) 0.2143(4) 0.0339(15) Uani 1 1 d . . . H3 H 0.4051 -0.2513 0.1927 0.041 Uiso 1 1 calc R . . C4 C 0.3523(7) -0.0144(10) 0.1631(5) 0.0350(16) Uani 1 1 d . . . H4 H 0.3706 -0.0194 0.1070 0.042 Uiso 1 1 calc R . . C5 C 0.3032(7) 0.1299(8) 0.1938(4) 0.0307(15) Uani 1 1 d . . . H5 H 0.2835 0.2231 0.1580 0.037 Uiso 1 1 calc R . . C6 C 0.2826(6) 0.1387(8) 0.2770(4) 0.0269(14) Uani 1 1 d . . . C7 C 0.2422(7) 0.3000(8) 0.3134(4) 0.0290(14) Uani 1 1 d . . . H7A H 0.3359 0.3598 0.3375 0.035 Uiso 1 1 calc R . . H7B H 0.1843 0.3680 0.2676 0.035 Uiso 1 1 calc R . . N1 N 0.1518(6) 0.2756(7) 0.3802(3) 0.0275(11) Uani 1 1 d . . . C8 C 0.1601(9) 0.4225(10) 0.4351(5) 0.0400(17) Uani 1 1 d . . . H8A H 0.2657 0.4464 0.4593 0.060 Uiso 1 1 calc R . . H8B H 0.1046 0.4019 0.4808 0.060 Uiso 1 1 calc R . . H8C H 0.1153 0.5165 0.4015 0.060 Uiso 1 1 calc R . . C9 C -0.0082(7) 0.2442(9) 0.3403(5) 0.0381(17) Uani 1 1 d . . . H9A H -0.0685 0.2313 0.3844 0.057 Uiso 1 1 calc R . . H9B H -0.0144 0.1438 0.3063 0.057 Uiso 1 1 calc R . . H9C H -0.0468 0.3369 0.3038 0.057 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 0.02216(13) 0.02530(15) 0.02209(15) -0.00044(10) 0.00452(8) -0.00012(9) Cl1 0.0299(8) 0.0326(8) 0.0440(10) -0.0068(7) 0.0080(7) -0.0064(6) Cl2 0.0297(7) 0.0266(8) 0.0305(9) 0.0034(6) 0.0000(6) -0.0022(6) C1 0.013(2) 0.034(4) 0.024(3) -0.005(3) 0.001(2) -0.001(2) C2 0.024(3) 0.029(4) 0.029(3) 0.003(3) 0.001(2) 0.006(2) C3 0.025(3) 0.045(4) 0.032(4) -0.007(3) 0.005(3) 0.009(3) C4 0.028(3) 0.054(5) 0.022(4) -0.011(3) 0.003(3) -0.002(3) C5 0.032(3) 0.037(4) 0.022(3) 0.007(3) 0.003(2) 0.003(3) C6 0.017(3) 0.035(4) 0.028(3) -0.002(3) 0.002(2) -0.001(2) C7 0.028(3) 0.029(3) 0.029(4) 0.009(3) 0.005(2) 0.007(3) N1 0.027(3) 0.026(3) 0.030(3) -0.008(2) 0.006(2) -0.002(2) C8 0.045(4) 0.035(4) 0.043(4) 0.000(3) 0.015(3) 0.008(3) C9 0.029(3) 0.035(4) 0.048(5) 0.011(3) 0.002(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 C1 2.225(7) . ? Bi1 N1 2.458(6) . ? Bi1 Cl1 2.5947(16) . ? Bi1 Cl2 2.8255(16) 3_656 ? Bi1 Cl2 2.8992(16) . ? Cl2 Bi1 2.8255(16) 3_656 ? C1 C2 1.374(9) . ? C1 C6 1.398(9) . ? C2 C3 1.382(9) . ? C3 C4 1.378(11) . ? C4 C5 1.382(10) . ? C5 C6 1.390(9) . ? C6 C7 1.513(9) . ? C7 N1 1.483(8) . ? N1 C8 1.482(9) . ? N1 C9 1.488(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Bi1 N1 74.9(2) . . ? C1 Bi1 Cl1 88.93(15) . . ? N1 Bi1 Cl1 96.13(13) . . ? C1 Bi1 Cl2 86.90(16) . 3_656 ? N1 Bi1 Cl2 158.00(13) . 3_656 ? Cl1 Bi1 Cl2 95.78(5) . 3_656 ? C1 Bi1 Cl2 85.90(15) . . ? N1 Bi1 Cl2 84.00(12) . . ? Cl1 Bi1 Cl2 174.61(5) . . ? Cl2 Bi1 Cl2 82.43(5) 3_656 . ? Bi1 Cl2 Bi1 97.57(5) 3_656 . ? C2 C1 C6 119.1(6) . . ? C2 C1 Bi1 125.3(5) . . ? C6 C1 Bi1 115.6(4) . . ? C1 C2 C3 120.6(6) . . ? C4 C3 C2 120.5(6) . . ? C3 C4 C5 119.6(6) . . ? C4 C5 C6 120.0(6) . . ? C5 C6 C1 120.0(6) . . ? C5 C6 C7 120.4(6) . . ? C1 C6 C7 119.5(6) . . ? N1 C7 C6 111.8(5) . . ? C8 N1 C7 110.6(5) . . ? C8 N1 C9 109.4(5) . . ? C7 N1 C9 109.5(5) . . ? C8 N1 Bi1 112.1(4) . . ? C7 N1 Bi1 105.0(4) . . ? C9 N1 Bi1 110.2(4) . . ? 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 Cl2 Bi1 -87.41(17) . . . 3_656 ? N1 Bi1 Cl2 Bi1 -162.64(13) . . . 3_656 ? Cl2 Bi1 Cl2 Bi1 0.0 3_656 . . 3_656 ? N1 Bi1 C1 C2 -165.5(5) . . . . ? Cl1 Bi1 C1 C2 -68.9(5) . . . . ? Cl2 Bi1 C1 C2 27.0(5) 3_656 . . . ? Cl2 Bi1 C1 C2 109.6(5) . . . . ? N1 Bi1 C1 C6 12.1(4) . . . . ? Cl1 Bi1 C1 C6 108.8(4) . . . . ? Cl2 Bi1 C1 C6 -155.4(4) 3_656 . . . ? Cl2 Bi1 C1 C6 -72.8(4) . . . . ? C6 C1 C2 C3 0.4(9) . . . . ? Bi1 C1 C2 C3 178.0(5) . . . . ? C1 C2 C3 C4 0.6(9) . . . . ? C2 C3 C4 C5 -2.1(10) . . . . ? C3 C4 C5 C6 2.7(10) . . . . ? C4 C5 C6 C1 -1.7(9) . . . . ? C4 C5 C6 C7 174.6(6) . . . . ? C2 C1 C6 C5 0.2(8) . . . . ? Bi1 C1 C6 C5 -177.6(4) . . . . ? C2 C1 C6 C7 -176.1(5) . . . . ? Bi1 C1 C6 C7 6.0(7) . . . . ? C5 C6 C7 N1 150.6(5) . . . . ? C1 C6 C7 N1 -33.1(8) . . . . ? C6 C7 N1 C8 159.6(5) . . . . ? C6 C7 N1 C9 -79.8(6) . . . . ? C6 C7 N1 Bi1 38.5(6) . . . . ? C1 Bi1 N1 C8 -147.6(5) . . . . ? Cl1 Bi1 N1 C8 125.2(4) . . . . ? Cl2 Bi1 N1 C8 -112.3(5) 3_656 . . . ? Cl2 Bi1 N1 C8 -60.2(4) . . . . ? C1 Bi1 N1 C7 -27.4(4) . . . . ? Cl1 Bi1 N1 C7 -114.7(4) . . . . ? Cl2 Bi1 N1 C7 7.8(6) 3_656 . . . ? Cl2 Bi1 N1 C7 59.9(4) . . . . ? C1 Bi1 N1 C9 90.4(5) . . . . ? Cl1 Bi1 N1 C9 3.2(4) . . . . ? Cl2 Bi1 N1 C9 125.6(4) 3_656 . . . ? Cl2 Bi1 N1 C9 177.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.125 _refine_diff_density_min -1.132 _refine_diff_density_rms 0.189