# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_lm1 _database_code_depnum_ccdc_archive 'CCDC 927200' #TrackingRef 'web_deposit_cif_file_0_LiMing_1363079714.a-BTC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H12 Bi Cl3 N6 S3' _chemical_formula_weight 543.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 Cc 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' _cell_length_a 8.503(13) _cell_length_b 11.983(17) _cell_length_c 15.39(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.509(18) _cell_angle_gamma 90.00 _cell_volume 1568(4) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 2033 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 12.14 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.723 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 301(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 7564 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3522 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.5665 2theta: 29.9187 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.5665 2theta: 29.9187 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.5665 2theta: 29.9187 ; _diffrn_orient_matrix_UB_11 -0.056867 _diffrn_orient_matrix_UB_12 0.068311 _diffrn_orient_matrix_UB_13 -0.077014 _diffrn_orient_matrix_UB_21 -0.067582 _diffrn_orient_matrix_UB_22 -0.001081 _diffrn_orient_matrix_UB_23 0.048944 _diffrn_orient_matrix_UB_31 0.021300 _diffrn_orient_matrix_UB_32 0.053210 _diffrn_orient_matrix_UB_33 0.030586 _diffrn_orient_matrix_type d*Trek _computing_data_collection ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(2) _refine_ls_number_reflns 3522 _refine_ls_number_parameters 102 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.070 _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 0.2721(5) 0.56555(3) 0.2915(2) 0.02907(15) Uani 1 1 d . . . S1 S 0.5186(11) 0.5774(8) 0.1759(5) 0.033(3) Uani 1 1 d . . . S2 S 0.1284(12) 0.7342(10) 0.1969(6) 0.045(3) Uani 1 1 d . . . S3 S 0.4161(11) 0.7355(11) 0.3825(6) 0.043(3) Uani 1 1 d . . . Cl1 Cl 0.0258(14) 0.5719(8) 0.4077(7) 0.049(3) Uani 1 1 d . . . Cl2 Cl 0.1179(12) 0.3972(11) 0.1829(6) 0.047(2) Uani 1 1 d . . . Cl3 Cl 0.4261(13) 0.4118(11) 0.3894(6) 0.051(2) Uani 1 1 d . . . C1 C 0.337(2) 0.7177(14) 0.4871(11) 0.020(5) Uiso 1 1 d D . . N1 N 0.370(3) 0.6285(15) 0.5332(14) 0.052(7) Uiso 1 1 d D . . H1A H 0.3170 0.6144 0.5794 0.062 Uiso 1 1 calc R . . H1B H 0.4432 0.5840 0.5173 0.062 Uiso 1 1 calc R . . N2 N 0.219(2) 0.7827(16) 0.5179(13) 0.060(6) Uiso 1 1 d D . . H2A H 0.1708 0.7639 0.5646 0.072 Uiso 1 1 calc R . . H2B H 0.1920 0.8424 0.4906 0.072 Uiso 1 1 calc R . . C2 C 0.201(4) 0.707(2) 0.0968(16) 0.058(10) Uiso 1 1 d D . . N3 N 0.149(2) 0.6279(15) 0.0474(14) 0.045(6) Uiso 1 1 d D . . H3A H 0.1678 0.6287 -0.0074 0.054 Uiso 1 1 calc R . . H3B H 0.0948 0.5744 0.0694 0.054 Uiso 1 1 calc R . . N4 N 0.287(2) 0.7919(13) 0.0621(12) 0.049(5) Uiso 1 1 d D . . H4A H 0.3058 0.7927 0.0074 0.058 Uiso 1 1 calc R . . H4B H 0.3216 0.8447 0.0949 0.058 Uiso 1 1 calc R . . C3 C 0.6821(17) 0.5757(10) 0.2473(10) 0.036(3) Uiso 1 1 d D . . N5 N 0.749(2) 0.4836(9) 0.2742(10) 0.055(4) Uiso 1 1 d D . . H5A H 0.8329 0.4864 0.3055 0.066 Uiso 1 1 calc R . . H5B H 0.7084 0.4201 0.2605 0.066 Uiso 1 1 calc R . . N6 N 0.7476(17) 0.6742(9) 0.2696(8) 0.047(3) Uiso 1 1 d D . . H6A H 0.8318 0.6756 0.3010 0.056 Uiso 1 1 calc R . . H6B H 0.7052 0.7356 0.2525 0.056 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 0.0299(2) 0.0273(2) 0.0300(2) 0.0008(7) 0.00001(15) -0.0001(8) S1 0.028(5) 0.046(5) 0.024(4) 0.002(3) 0.011(4) -0.002(3) S2 0.056(7) 0.036(5) 0.043(6) 0.003(4) 0.000(5) 0.020(5) S3 0.052(7) 0.053(6) 0.025(4) -0.003(4) 0.008(4) -0.011(5) Cl1 0.041(6) 0.051(6) 0.054(6) 0.001(4) -0.014(4) -0.002(4) Cl2 0.058(4) 0.032(3) 0.051(4) -0.023(3) 0.008(3) -0.018(3) Cl3 0.063(5) 0.048(5) 0.043(4) 0.028(3) 0.020(3) 0.021(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 Cl3 2.709(11) . ? Bi1 S3 2.752(12) . ? Bi1 S1 2.765(9) . ? Bi1 Cl1 2.767(12) . ? Bi1 S2 2.769(11) . ? Bi1 Cl2 2.923(11) . ? S1 C3 1.765(18) . ? S2 C2 1.70(3) . ? S3 C1 1.762(19) . ? C1 N1 1.311(13) . ? C1 N2 1.362(14) . ? C2 N3 1.296(15) . ? C2 N4 1.358(15) . ? C3 N5 1.306(13) . ? C3 N6 1.348(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl3 Bi1 S3 90.5(5) . . ? Cl3 Bi1 S1 91.6(3) . . ? S3 Bi1 S1 87.3(3) . . ? Cl3 Bi1 Cl1 91.4(3) . . ? S3 Bi1 Cl1 89.2(3) . . ? S1 Bi1 Cl1 175.50(10) . . ? Cl3 Bi1 S2 175.9(5) . . ? S3 Bi1 S2 85.42(14) . . ? S1 Bi1 S2 87.6(3) . . ? Cl1 Bi1 S2 89.3(3) . . ? Cl3 Bi1 Cl2 93.48(17) . . ? S3 Bi1 Cl2 175.4(4) . . ? S1 Bi1 Cl2 90.3(3) . . ? Cl1 Bi1 Cl2 92.9(3) . . ? S2 Bi1 Cl2 90.5(5) . . ? C3 S1 Bi1 101.3(6) . . ? C2 S2 Bi1 100.2(12) . . ? C1 S3 Bi1 101.8(9) . . ? N1 C1 N2 115.4(15) . . ? N1 C1 S3 120.9(14) . . ? N2 C1 S3 122.5(13) . . ? N3 C2 N4 120.0(19) . . ? N3 C2 S2 123.0(18) . . ? N4 C2 S2 114.7(16) . . ? N5 C3 N6 118.8(12) . . ? N5 C3 S1 122.9(11) . . ? N6 C3 S1 118.1(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.755 _refine_diff_density_min -1.694 _refine_diff_density_rms 0.206 data_bsc3 _database_code_depnum_ccdc_archive 'CCDC 927201' #TrackingRef 'web_deposit_cif_file_1_LiMing_1363079714.b-BTC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H12 Bi Cl3 N6 S3' _chemical_formula_weight 543.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M P3 _symmetry_Int_Tables_number 143 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' _cell_length_a 13.5930(11) _cell_length_b 13.5930(11) _cell_length_c 7.1406(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1142.6(2) _cell_formula_units_Z 3 _cell_measurement_temperature 299(2) _cell_measurement_reflns_used 2659 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 762 _exptl_absorpt_coefficient_mu 12.495 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 299(2) _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _diffrn_source_current 12.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_specimen_support Fiber _diffrn_detector CCD _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 11921 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0832 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.41 _reflns_number_total 3491 _reflns_number_gt 2749 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_details ; scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.5485 2theta: 29.9423 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.5485 2theta: 29.9423 scan: Number of images: 180 Slice: -60.0000 - 120.0000 Image width: 1.0000 Exp time: 16.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.5485 2theta: 29.9423 ; _diffrn_orient_matrix_UB_11 0.024541 _diffrn_orient_matrix_UB_12 -0.062498 _diffrn_orient_matrix_UB_13 0.052038 _diffrn_orient_matrix_UB_21 0.082701 _diffrn_orient_matrix_UB_22 -0.015012 _diffrn_orient_matrix_UB_23 0.012304 _diffrn_orient_matrix_UB_31 0.000274 _diffrn_orient_matrix_UB_32 0.089673 _diffrn_orient_matrix_UB_33 0.107569 _diffrn_orient_matrix_type d*Trek _computing_data_collection ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r1 (Rigaku, 2009) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refined as a 2-component inversion twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0076P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.47(3) _chemical_absolute_configuration ? _refine_ls_number_reflns 3491 _refine_ls_number_parameters 101 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.0000 0.0000 0.12952(15) 0.0263(5) Uani 1 3 d S T P . . Bi2 Bi 0.3333 0.6667 0.8807(5) 0.0267(2) Uani 1 3 d S T P . . Bi3 Bi 0.6667 0.3333 0.63178(12) 0.0241(5) Uani 1 3 d S T P . . S1 S 0.1366(11) 0.5987(9) 0.1054(18) 0.038(3) Uani 1 1 d . . . . . S2 S 0.6200(8) 0.4722(9) 0.4130(16) 0.037(3) Uani 1 1 d . . . . . S3 S 0.1995(10) 0.4713(11) 0.6530(19) 0.038(3) Uani 1 1 d . . . . . Cl1 Cl 0.9639(10) 0.1491(10) 0.9190(15) 0.048(3) Uani 1 1 d . . . . . Cl2 Cl 0.4810(9) 0.2945(8) 0.8365(15) 0.038(3) Uani 1 1 d . . . . . Cl3 Cl 0.1381(10) 0.1801(10) 0.3459(17) 0.055(3) Uani 1 1 d . . . . . C1 C 0.0652(17) 0.4503(17) 0.079(3) 0.011(4) Uiso 1 1 d . . . . . N1 N -0.0223(18) 0.398(2) -0.028(3) 0.036(6) Uiso 1 1 d . . . . . H1A H -0.0524 0.3261 -0.0458 0.043 Uiso 1 1 calc R U . . . H1B H -0.0507 0.4350 -0.0809 0.043 Uiso 1 1 calc R U . . . N2 N 0.101(2) 0.382(2) 0.153(3) 0.058(8) Uiso 1 1 d . . . . . H2A H 0.0656 0.3108 0.1272 0.069 Uiso 1 1 calc R U . . . H2B H 0.1590 0.4102 0.2260 0.069 Uiso 1 1 calc R U . . . C2 C 0.7518(15) 0.5976(14) 0.402(3) 0.040(4) Uiso 1 1 d . . . . . N3 N 0.8340(14) 0.6075(14) 0.286(2) 0.050(5) Uiso 1 1 d . . . . . H3A H 0.8959 0.6716 0.2755 0.060 Uiso 1 1 calc R U . . . H3B H 0.8249 0.5497 0.2229 0.060 Uiso 1 1 calc R U . . . N4 N 0.7733(14) 0.6925(15) 0.496(2) 0.054(5) Uiso 1 1 d . . . . . H4A H 0.8368 0.7544 0.4795 0.064 Uiso 1 1 calc R U . . . H4B H 0.7236 0.6911 0.5719 0.064 Uiso 1 1 calc R U . . . C3 C 0.275(3) 0.406(3) 0.679(5) 0.071(11) Uiso 1 1 d . . . . . N5 N 0.229(2) 0.3028(19) 0.780(4) 0.048(7) Uiso 1 1 d . . . . . H5A H 0.2652 0.2660 0.7842 0.058 Uiso 1 1 calc R U . . . H5B H 0.1649 0.2767 0.8366 0.058 Uiso 1 1 calc R U . . . N6 N 0.3740(17) 0.4442(17) 0.593(3) 0.032(5) Uiso 1 1 d . . . . . H6A H 0.4089 0.4062 0.5990 0.038 Uiso 1 1 calc R U . . . H6B H 0.4032 0.5069 0.5311 0.038 Uiso 1 1 calc R U . . . 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 0.0172(7) 0.0172(7) 0.0446(13) 0.000 0.000 0.0086(3) Bi2 0.0241(3) 0.0241(3) 0.0318(5) 0.000 0.000 0.01206(15) Bi3 0.0262(8) 0.0262(8) 0.0199(9) 0.000 0.000 0.0131(4) S1 0.041(6) 0.022(5) 0.043(6) -0.004(4) 0.007(5) 0.011(4) S2 0.017(4) 0.030(5) 0.051(7) 0.006(5) -0.010(4) 0.001(4) S3 0.030(5) 0.037(6) 0.051(6) -0.005(5) -0.008(5) 0.019(5) Cl1 0.065(7) 0.055(6) 0.037(5) 0.009(5) -0.004(5) 0.041(5) Cl2 0.034(6) 0.023(4) 0.064(7) 0.012(4) 0.013(5) 0.019(4) Cl3 0.053(7) 0.044(7) 0.062(7) -0.024(5) -0.026(6) 0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 Cl3 2.703(11) . ? Bi1 Cl3 2.703(11) 3 ? Bi1 Cl3 2.703(11) 2 ? Bi1 Cl1 2.757(11) 2_544 ? Bi1 Cl1 2.757(11) 1_454 ? Bi1 Cl1 2.757(11) 3_664 ? Bi2 S1 2.848(13) 3_566 ? Bi2 S1 2.848(13) 1_556 ? Bi2 S1 2.848(13) 2_666 ? Bi2 S3 2.859(13) . ? Bi2 S3 2.859(13) 3_565 ? Bi2 S3 2.859(13) 2_665 ? Bi3 Cl2 2.730(11) . ? Bi3 Cl2 2.730(11) 2_655 ? Bi3 Cl2 2.730(11) 3_665 ? Bi3 S2 2.758(11) 2_655 ? Bi3 S2 2.758(11) 3_665 ? Bi3 S2 2.758(11) . ? S1 C1 1.76(2) . ? S1 Bi2 2.848(13) 1_554 ? S2 C2 1.751(19) . ? S3 C3 1.66(3) . ? Cl1 Bi1 2.757(11) 1_656 ? C1 N1 1.29(3) . ? C1 N2 1.35(3) . ? C2 N3 1.34(2) . ? C2 N4 1.35(2) . ? C3 N6 1.33(4) . ? C3 N5 1.42(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl3 Bi1 Cl3 90.6(4) . 3 ? Cl3 Bi1 Cl3 90.6(4) . 2 ? Cl3 Bi1 Cl3 90.6(4) 3 2 ? Cl3 Bi1 Cl1 177.4(4) . 2_544 ? Cl3 Bi1 Cl1 89.5(4) 3 2_544 ? Cl3 Bi1 Cl1 86.8(4) 2 2_544 ? Cl3 Bi1 Cl1 86.8(4) . 1_454 ? Cl3 Bi1 Cl1 177.4(4) 3 1_454 ? Cl3 Bi1 Cl1 89.5(4) 2 1_454 ? Cl1 Bi1 Cl1 93.1(3) 2_544 1_454 ? Cl3 Bi1 Cl1 89.5(4) . 3_664 ? Cl3 Bi1 Cl1 86.8(4) 3 3_664 ? Cl3 Bi1 Cl1 177.4(4) 2 3_664 ? Cl1 Bi1 Cl1 93.1(3) 2_544 3_664 ? Cl1 Bi1 Cl1 93.1(3) 1_454 3_664 ? S1 Bi2 S1 91.4(4) 3_566 1_556 ? S1 Bi2 S1 91.4(4) 3_566 2_666 ? S1 Bi2 S1 91.4(4) 1_556 2_666 ? S1 Bi2 S3 178.4(4) 3_566 . ? S1 Bi2 S3 87.8(3) 1_556 . ? S1 Bi2 S3 90.0(3) 2_666 . ? S1 Bi2 S3 87.8(3) 3_566 3_565 ? S1 Bi2 S3 90.0(3) 1_556 3_565 ? S1 Bi2 S3 178.4(4) 2_666 3_565 ? S3 Bi2 S3 90.8(4) . 3_565 ? S1 Bi2 S3 90.0(3) 3_566 2_665 ? S1 Bi2 S3 178.4(4) 1_556 2_665 ? S1 Bi2 S3 87.8(3) 2_666 2_665 ? S3 Bi2 S3 90.8(4) . 2_665 ? S3 Bi2 S3 90.8(4) 3_565 2_665 ? Cl2 Bi3 Cl2 94.0(3) . 2_655 ? Cl2 Bi3 Cl2 94.0(3) . 3_665 ? Cl2 Bi3 Cl2 94.0(3) 2_655 3_665 ? Cl2 Bi3 S2 89.0(3) . 2_655 ? Cl2 Bi3 S2 85.9(3) 2_655 2_655 ? Cl2 Bi3 S2 177.0(3) 3_665 2_655 ? Cl2 Bi3 S2 177.0(3) . 3_665 ? Cl2 Bi3 S2 89.0(3) 2_655 3_665 ? Cl2 Bi3 S2 85.9(3) 3_665 3_665 ? S2 Bi3 S2 91.1(4) 2_655 3_665 ? Cl2 Bi3 S2 85.9(3) . . ? Cl2 Bi3 S2 177.0(3) 2_655 . ? Cl2 Bi3 S2 89.0(3) 3_665 . ? S2 Bi3 S2 91.1(4) 2_655 . ? S2 Bi3 S2 91.1(4) 3_665 . ? C1 S1 Bi2 101.6(8) . 1_554 ? C2 S2 Bi3 102.6(7) . . ? C3 S3 Bi2 98.9(13) . . ? N1 C1 N2 114(2) . . ? N1 C1 S1 121.7(19) . . ? N2 C1 S1 124.3(17) . . ? N3 C2 N4 116.0(17) . . ? N3 C2 S2 121.4(16) . . ? N4 C2 S2 122.4(16) . . ? N6 C3 N5 119(3) . . ? N6 C3 S3 121(3) . . ? N5 C3 S3 120(3) . . ? _refine_diff_density_max 1.248 _refine_diff_density_min -1.367 _refine_diff_density_rms 0.189 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 1.000