# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound1 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.000 0.000 -0.003 495 72 ' ' _platon_squeeze_details ; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 B2 N18 Na2 S6' _chemical_formula_sum 'C18 H26 B2 N18 Na2 S6' _chemical_formula_weight 754.53 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' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 '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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P -3 1 c' _symmetry_space_group_name_Hall '-P 3 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' 'x, x-y, -z+1/2' '-x+y, y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' '-x, -x+y, z-1/2' 'x-y, -y, z-1/2' _cell_length_a 13.1216(3) _cell_length_b 13.1216(3) _cell_length_c 13.5926(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2026.78(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22489 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8904 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37797 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _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 3.00 _diffrn_reflns_theta_max 30.00 _reflns_number_total 1991 _reflns_number_gt 1649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; The crystal includes a highly disordered solvent on a threefold axis, which could not be determined reliably as the used solvent toluene or thf. It was treated with the SQUEEZE procedure of Platon program Reference : Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Spek, A.L. (2009). Acta Cryst. D65, 148-155. The sum formular and further calculations disregard this electron density. 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^)+(0.0675P)^2^+1.2195P] 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 1991 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.175 _refine_ls_restrained_S_all 1.175 _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 S1 S 0.47500(5) 0.11228(5) -0.14645(4) 0.03565(19) Uani 1 1 d . . . Na1 Na 0.6667 0.3333 -0.2500 0.0298(4) Uani 1 6 d S . . Na2 Na 0.6667 0.3333 0.2500 0.0261(4) Uani 1 6 d S . . N1 N 0.55707(13) 0.22016(13) 0.03235(10) 0.0215(3) Uani 1 1 d . . . N2 N 0.52652(15) 0.20077(15) 0.13115(11) 0.0285(4) Uani 1 1 d . . . N3 N 0.39477(15) 0.05476(14) 0.04126(12) 0.0280(4) Uani 1 1 d . . . C1 C 0.47668(16) 0.13090(16) -0.02338(14) 0.0236(4) Uani 1 1 d . . . C2 C 0.4292(2) 0.10061(19) 0.13299(15) 0.0336(5) Uani 1 1 d . . . H2 H 0.3871 0.0637 0.1914 0.040 Uiso 1 1 calc R . . C3 C 0.2905(2) -0.05632(19) 0.01661(19) 0.0416(5) Uani 1 1 d . . . H3A H 0.2715 -0.1119 0.0711 0.062 Uiso 1 1 calc R . . H3B H 0.3055 -0.0888 -0.0430 0.062 Uiso 1 1 calc R . . H3C H 0.2242 -0.0432 0.0051 0.062 Uiso 1 1 calc R . . B1 B 0.6667 0.3333 -0.0034(2) 0.0211(6) Uani 1 3 d S . . H1 H 0.6667 0.3333 -0.0769 0.025 Uiso 1 3 calc SR . . 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 S1 0.0413(3) 0.0333(3) 0.0255(3) -0.01098(19) -0.00326(19) 0.0135(2) Na1 0.0354(6) 0.0354(6) 0.0185(8) 0.000 0.000 0.0177(3) Na2 0.0316(6) 0.0316(6) 0.0152(8) 0.000 0.000 0.0158(3) N1 0.0239(7) 0.0229(7) 0.0176(7) -0.0004(5) -0.0006(5) 0.0116(6) N2 0.0309(8) 0.0288(8) 0.0191(7) 0.0041(6) 0.0010(6) 0.0100(7) N3 0.0273(8) 0.0205(7) 0.0329(8) -0.0004(6) -0.0011(6) 0.0096(6) C1 0.0243(8) 0.0219(8) 0.0277(8) -0.0026(6) -0.0016(6) 0.0139(7) C2 0.0344(11) 0.0293(10) 0.0288(9) 0.0049(7) 0.0032(8) 0.0097(8) C3 0.0365(12) 0.0216(10) 0.0538(14) -0.0053(9) -0.0015(10) 0.0050(9) B1 0.0240(9) 0.0240(9) 0.0154(13) 0.000 0.000 0.0120(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 S1 C1 1.6891(19) . ? S1 Na1 3.0699(6) . ? Na1 S1 3.0699(6) 2_655 ? Na1 S1 3.0699(6) 6_654 ? Na1 S1 3.0699(6) 4_664 ? Na1 S1 3.0699(6) 5_554 ? Na1 S1 3.0699(6) 3_665 ? Na1 B1 3.352(3) . ? Na1 H1 2.3524 . ? Na2 N2 2.4121(17) 2_655 ? Na2 N2 2.4121(17) . ? Na2 N2 2.4121(17) 6_655 ? Na2 N2 2.4122(17) 4_665 ? Na2 N2 2.4122(17) 3_665 ? Na2 N2 2.4122(17) 5 ? N1 C1 1.350(2) . ? N1 N2 1.388(2) . ? N1 B1 1.5406(18) . ? N2 C2 1.296(3) . ? N3 C2 1.360(3) . ? N3 C1 1.361(2) . ? N3 C3 1.454(3) . ? C2 H2 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? B1 N1 1.5406(18) 2_655 ? B1 N1 1.5407(18) 3_665 ? B1 H1 1.0000 . ? 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 S1 Na1 111.84(7) . . ? S1 Na1 S1 89.62(2) 2_655 6_654 ? S1 Na1 S1 70.179(19) 2_655 4_664 ? S1 Na1 S1 100.645(11) 6_654 4_664 ? S1 Na1 S1 167.51(2) 2_655 5_554 ? S1 Na1 S1 100.645(11) 6_654 5_554 ? S1 Na1 S1 100.643(11) 4_664 5_554 ? S1 Na1 S1 100.644(11) 2_655 . ? S1 Na1 S1 70.179(19) 6_654 . ? S1 Na1 S1 167.51(2) 4_664 . ? S1 Na1 S1 89.62(2) 5_554 . ? S1 Na1 S1 100.643(11) 2_655 3_665 ? S1 Na1 S1 167.51(2) 6_654 3_665 ? S1 Na1 S1 89.62(2) 4_664 3_665 ? S1 Na1 S1 70.178(19) 5_554 3_665 ? S1 Na1 S1 100.645(11) . 3_665 ? H1 Na1 S1 62.7 . 2_655 ? H1 Na1 S1 117.3 . 6_654 ? H1 Na1 S1 117.3 . 4_664 ? H1 Na1 S1 117.3 . 5_554 ? H1 Na1 S1 62.7 . . ? H1 Na1 S1 62.7 . 3_665 ? H1 Na1 B1 0.0 . . ? S1 Na1 B1 62.711(9) 2_655 . ? S1 Na1 B1 117.288(9) 6_654 . ? S1 Na1 B1 117.288(9) 4_664 . ? S1 Na1 B1 117.288(9) 5_554 . ? S1 Na1 B1 62.711(9) . . ? S1 Na1 B1 62.712(9) 3_665 . ? N2 Na2 N2 80.05(6) 2_655 . ? N2 Na2 N2 97.37(8) 2_655 6_655 ? N2 Na2 N2 102.70(8) . 6_655 ? N2 Na2 N2 102.71(8) 2_655 4_665 ? N2 Na2 N2 175.91(9) . 4_665 ? N2 Na2 N2 80.05(6) 6_655 4_665 ? N2 Na2 N2 80.05(6) 2_655 3_665 ? N2 Na2 N2 80.05(6) . 3_665 ? N2 Na2 N2 175.91(9) 6_655 3_665 ? N2 Na2 N2 97.37(8) 4_665 3_665 ? N2 Na2 N2 175.91(9) 2_655 5 ? N2 Na2 N2 97.37(8) . 5 ? N2 Na2 N2 80.05(6) 6_655 5 ? N2 Na2 N2 80.05(6) 4_665 5 ? N2 Na2 N2 102.70(8) 3_665 5 ? C1 N1 N2 110.80(15) . . ? C1 N1 B1 127.39(17) . . ? N2 N1 B1 121.76(17) . . ? C2 N2 N1 104.61(16) . . ? C2 N2 Na2 136.68(13) . . ? N1 N2 Na2 118.01(11) . . ? C2 N3 C1 107.54(16) . . ? C2 N3 C3 126.36(18) . . ? C1 N3 C3 126.10(18) . . ? N1 C1 N3 105.21(16) . . ? N1 C1 S1 128.99(15) . . ? N3 C1 S1 125.79(14) . . ? N2 C2 N3 111.84(18) . . ? N2 C2 H2 124.1 . . ? N3 C2 H2 124.1 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 B1 N1 110.55(12) . 2_655 ? N1 B1 N1 110.55(12) . 3_665 ? N1 B1 N1 110.55(12) 2_655 3_665 ? N1 B1 H1 108.4 . . ? N1 B1 H1 108.4 2_655 . ? N1 B1 H1 108.4 3_665 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.509 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 952327' ####################################################################### # # 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_compound3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 B2 K N18 Na S6, 2(C3 H7 N O)' _chemical_formula_sum 'C24 H40 B2 K N20 Na O2 S6' _chemical_formula_weight 916.83 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' B B 0.0013 0.0007 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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' _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 10.43890(10) _cell_length_b 10.58020(10) _cell_length_c 10.62060(10) _cell_angle_alpha 93.3316(6) _cell_angle_beta 96.2652(6) _cell_angle_gamma 116.4806(7) _cell_volume 1036.120(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29205 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8657 _exptl_absorpt_correction_T_max 0.9075 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45873 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 30.00 _reflns_number_total 6042 _reflns_number_gt 5370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.3951P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6042 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 K1 K 0.5000 0.5000 0.5000 0.01517(7) Uani 1 2 d S . . Na1 Na 0.0000 0.5000 0.0000 0.01340(12) Uani 1 2 d S . . S1 S 0.49833(3) 0.38615(3) 0.21503(3) 0.01621(6) Uani 1 1 d . . . S2 S 0.52817(3) 0.80299(3) 0.41312(2) 0.01359(6) Uani 1 1 d . . . S3 S 0.15997(3) 0.36457(3) 0.52552(2) 0.01582(6) Uani 1 1 d . . . N1 N 0.25915(9) 0.42264(9) 0.12724(8) 0.01093(15) Uani 1 1 d . . . N2 N 0.16947(10) 0.40046(10) 0.01274(8) 0.01454(17) Uani 1 1 d . . . N3 N 0.33348(10) 0.32883(9) -0.01649(8) 0.01414(17) Uani 1 1 d . . . N4 N 0.28865(9) 0.65828(9) 0.22718(8) 0.01088(15) Uani 1 1 d . . . N5 N 0.21374(10) 0.68899(10) 0.12726(8) 0.01454(17) Uani 1 1 d . . . N6 N 0.39697(10) 0.88623(9) 0.22444(9) 0.01422(17) Uani 1 1 d . . . N7 N 0.09435(9) 0.42936(9) 0.28637(8) 0.01054(15) Uani 1 1 d . . . N8 N -0.02542(9) 0.42195(10) 0.20854(8) 0.01385(17) Uani 1 1 d . . . N9 N -0.08885(9) 0.33387(9) 0.38742(8) 0.01317(16) Uani 1 1 d . . . C1 C 0.36151(11) 0.37968(10) 0.11027(10) 0.01205(18) Uani 1 1 d . . . B1 B 0.24773(11) 0.50244(11) 0.24919(10) 0.01030(19) Uani 1 1 d . . . H1 H 0.3219(13) 0.5026(13) 0.3251(12) 0.006(3) Uiso 1 1 d . . . C2 C 0.21815(12) 0.34495(12) -0.07049(10) 0.0162(2) Uani 1 1 d . . . H2 H 0.1801(16) 0.3181(16) -0.1587(15) 0.023(4) Uiso 1 1 d . . . C3 C 0.41619(13) 0.27217(13) -0.08144(11) 0.0190(2) Uani 1 1 d . . . H3B H 0.5141(17) 0.3212(16) -0.0445(15) 0.023(4) Uiso 1 1 d . . . H3C H 0.4079(17) 0.2891(17) -0.1677(16) 0.027(4) Uiso 1 1 d . . . H3A H 0.3805(17) 0.1715(17) -0.0739(15) 0.026(4) Uiso 1 1 d . . . C4 C 0.40216(10) 0.77890(10) 0.28823(9) 0.01103(17) Uani 1 1 d . . . C5 C 0.28215(12) 0.82636(11) 0.12882(10) 0.0166(2) Uani 1 1 d . . . H5 H 0.2547(17) 0.8763(17) 0.0709(15) 0.028(4) Uiso 1 1 d . . . C6 C 0.50044(13) 1.03621(12) 0.25325(12) 0.0206(2) Uani 1 1 d . . . H6B H 0.5957(19) 1.0490(18) 0.2368(17) 0.035(4) Uiso 1 1 d . . . H6C H 0.4650(18) 1.0899(18) 0.2010(16) 0.033(4) Uiso 1 1 d . . . H6A H 0.5066(17) 1.0668(17) 0.3401(16) 0.028(4) Uiso 1 1 d . . . C7 C 0.05684(11) 0.37629(10) 0.39732(9) 0.01139(17) Uani 1 1 d . . . C8 C -0.13226(11) 0.36474(11) 0.27262(10) 0.01530(19) Uani 1 1 d . . . H8 H -0.2296(16) 0.3462(15) 0.2451(14) 0.019(3) Uiso 1 1 d . . . C9 C -0.17939(12) 0.27330(12) 0.48491(11) 0.0177(2) Uani 1 1 d . . . H9B H -0.1217(18) 0.3096(17) 0.5679(16) 0.030(4) Uiso 1 1 d . . . H9A H -0.2552(18) 0.3006(17) 0.4803(15) 0.029(4) Uiso 1 1 d . . . H9C H -0.2194(17) 0.1718(18) 0.4729(15) 0.026(4) Uiso 1 1 d . . . O1 O 0.15753(14) 0.94558(12) 0.90788(12) 0.0540(4) Uani 1 1 d . . . N10 N -0.00521(11) 0.95618(10) 0.75423(10) 0.02005(19) Uani 1 1 d . . . C10 C 0.03508(18) 0.92540(14) 0.86668(13) 0.0338(3) Uani 1 1 d . . . H10 H -0.045(2) 0.885(2) 0.9180(18) 0.042(5) Uiso 1 1 d . . . C11 C 0.09661(14) 1.01298(14) 0.66515(12) 0.0223(2) Uani 1 1 d . . . H11B H 0.0668(16) 0.9496(16) 0.5876(15) 0.023(4) Uiso 1 1 d . . . H11C H 0.1042(19) 1.1044(19) 0.6444(16) 0.035(4) Uiso 1 1 d . . . H11A H 0.190(2) 1.029(2) 0.7015(18) 0.041(5) Uiso 1 1 d . . . C12 C -0.15290(15) 0.93025(17) 0.71164(18) 0.0357(3) Uani 1 1 d . . . H12B H -0.151(2) 1.024(2) 0.6927(19) 0.048(5) Uiso 1 1 d . . . H12C H -0.206(2) 0.896(2) 0.781(2) 0.050(5) Uiso 1 1 d . . . H12A H -0.197(2) 0.858(2) 0.633(2) 0.054(6) Uiso 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 K1 0.01388(14) 0.02004(15) 0.01311(14) 0.00375(11) -0.00047(11) 0.00943(12) Na1 0.0117(3) 0.0174(3) 0.0107(3) 0.0014(2) -0.0012(2) 0.0069(2) S1 0.01526(12) 0.02095(13) 0.01727(12) 0.00260(9) 0.00208(9) 0.01257(10) S2 0.01128(11) 0.01503(12) 0.01200(11) -0.00007(9) -0.00124(8) 0.00469(9) S3 0.01501(12) 0.01998(13) 0.01308(12) 0.00695(9) 0.00242(9) 0.00788(10) N1 0.0097(4) 0.0129(4) 0.0103(4) 0.0011(3) 0.0008(3) 0.0055(3) N2 0.0140(4) 0.0179(4) 0.0107(4) -0.0004(3) -0.0006(3) 0.0071(3) N3 0.0149(4) 0.0150(4) 0.0134(4) 0.0006(3) 0.0044(3) 0.0073(3) N4 0.0105(4) 0.0126(4) 0.0097(4) 0.0015(3) -0.0001(3) 0.0058(3) N5 0.0150(4) 0.0155(4) 0.0131(4) 0.0023(3) -0.0021(3) 0.0078(3) N6 0.0150(4) 0.0114(4) 0.0150(4) 0.0021(3) 0.0002(3) 0.0053(3) N7 0.0092(4) 0.0132(4) 0.0096(4) 0.0016(3) 0.0006(3) 0.0056(3) N8 0.0097(4) 0.0186(4) 0.0130(4) 0.0021(3) 0.0002(3) 0.0065(3) N9 0.0108(4) 0.0150(4) 0.0138(4) 0.0028(3) 0.0042(3) 0.0053(3) C1 0.0124(4) 0.0104(4) 0.0139(4) 0.0025(3) 0.0046(3) 0.0050(4) B1 0.0100(5) 0.0111(5) 0.0099(5) 0.0012(4) 0.0018(4) 0.0049(4) C2 0.0165(5) 0.0195(5) 0.0124(5) -0.0003(4) 0.0020(4) 0.0083(4) C3 0.0205(5) 0.0195(5) 0.0200(5) -0.0005(4) 0.0088(4) 0.0108(4) C4 0.0109(4) 0.0120(4) 0.0111(4) 0.0011(3) 0.0033(3) 0.0057(3) C5 0.0181(5) 0.0159(5) 0.0156(5) 0.0028(4) -0.0012(4) 0.0083(4) C6 0.0219(6) 0.0109(5) 0.0240(6) 0.0016(4) -0.0008(4) 0.0041(4) C7 0.0115(4) 0.0100(4) 0.0128(4) 0.0011(3) 0.0033(3) 0.0048(3) C8 0.0110(4) 0.0187(5) 0.0157(5) 0.0022(4) 0.0018(4) 0.0063(4) C9 0.0157(5) 0.0189(5) 0.0189(5) 0.0056(4) 0.0092(4) 0.0064(4) O1 0.0568(7) 0.0334(6) 0.0446(7) 0.0196(5) -0.0248(6) 0.0021(5) N10 0.0191(5) 0.0176(4) 0.0215(5) 0.0039(4) 0.0043(4) 0.0063(4) C10 0.0450(8) 0.0176(6) 0.0217(6) 0.0061(5) 0.0005(6) -0.0002(5) C11 0.0207(6) 0.0233(6) 0.0208(6) 0.0056(4) 0.0042(4) 0.0074(5) C12 0.0197(6) 0.0337(7) 0.0528(9) -0.0006(7) 0.0068(6) 0.0118(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 S1 3.1870(3) . ? K1 S1 3.1870(3) 2_666 ? K1 S3 3.2319(3) . ? K1 S3 3.2320(3) 2_666 ? K1 S2 3.2828(3) 2_666 ? K1 S2 3.2828(3) . ? K1 B1 3.5452(11) . ? K1 B1 3.5452(11) 2_666 ? K1 H1 2.491(12) . ? Na1 N8 2.4090(9) . ? Na1 N8 2.4090(9) 2_565 ? Na1 N5 2.4191(9) . ? Na1 N5 2.4191(9) 2_565 ? Na1 N2 2.4255(9) . ? Na1 N2 2.4256(9) 2_565 ? S1 C1 1.6852(10) . ? S2 C4 1.6838(10) . ? S3 C7 1.6873(10) . ? N1 C1 1.3589(13) . ? N1 N2 1.3901(11) . ? N1 B1 1.5494(13) . ? N2 C2 1.2994(14) . ? N3 C2 1.3607(14) . ? N3 C1 1.3701(13) . ? N3 C3 1.4574(13) . ? N4 C4 1.3568(13) . ? N4 N5 1.3888(11) . ? N4 B1 1.5474(13) . ? N5 C5 1.3006(14) . ? N6 C5 1.3608(13) . ? N6 C4 1.3739(13) . ? N6 C6 1.4564(14) . ? N7 C7 1.3560(13) . ? N7 N8 1.3899(11) . ? N7 B1 1.5450(13) . ? N8 C8 1.2981(14) . ? N9 C8 1.3625(13) . ? N9 C7 1.3698(13) . ? N9 C9 1.4582(13) . ? B1 H1 1.054(12) . ? C2 H2 0.950(15) . ? C3 H3B 0.940(15) . ? C3 H3C 0.946(17) . ? C3 H3A 0.971(16) . ? C5 H5 0.935(16) . ? C6 H6B 0.979(18) . ? C6 H6C 0.973(17) . ? C6 H6A 0.945(17) . ? C8 H8 0.953(15) . ? C9 H9B 0.962(17) . ? C9 H9A 0.953(17) . ? C9 H9C 0.958(16) . ? O1 C10 1.223(2) . ? N10 C10 1.3293(17) . ? N10 C11 1.4498(15) . ? N10 C12 1.4536(17) . ? C10 H10 0.995(19) . ? C11 H11B 0.959(15) . ? C11 H11C 0.975(18) . ? C11 H11A 0.947(19) . ? C12 H12B 1.02(2) . ? C12 H12C 0.96(2) . ? C12 H12A 1.01(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 S1 K1 S1 180.0 . 2_666 ? S1 K1 S3 103.218(7) . . ? S1 K1 S3 76.782(7) 2_666 . ? S1 K1 S3 76.781(7) . 2_666 ? S1 K1 S3 103.218(7) 2_666 2_666 ? S3 K1 S3 179.999(11) . 2_666 ? S1 K1 S2 88.376(7) . 2_666 ? S1 K1 S2 91.625(7) 2_666 2_666 ? S3 K1 S2 83.946(7) . 2_666 ? S3 K1 S2 96.054(6) 2_666 2_666 ? S1 K1 S2 91.625(7) . . ? S1 K1 S2 88.375(7) 2_666 . ? S3 K1 S2 96.054(6) . . ? S3 K1 S2 83.946(6) 2_666 . ? S2 K1 S2 180.0 2_666 . ? S1 K1 B1 60.256(18) . . ? S1 K1 B1 119.744(18) 2_666 . ? S3 K1 B1 59.760(18) . . ? S3 K1 B1 120.240(18) 2_666 . ? S2 K1 B1 120.148(18) 2_666 . ? S2 K1 B1 59.852(18) . . ? S1 K1 B1 119.745(18) . 2_666 ? S1 K1 B1 60.255(18) 2_666 2_666 ? S3 K1 B1 120.240(18) . 2_666 ? S3 K1 B1 59.761(18) 2_666 2_666 ? S2 K1 B1 59.853(18) 2_666 2_666 ? S2 K1 B1 120.147(18) . 2_666 ? B1 K1 B1 180.0 . 2_666 ? S1 K1 H1 60.8(3) . . ? S1 K1 H1 119.2(3) 2_666 . ? S3 K1 H1 59.4(3) . . ? S3 K1 H1 120.6(3) 2_666 . ? S2 K1 H1 120.3(3) 2_666 . ? S2 K1 H1 59.7(3) . . ? B1 K1 H1 0.5(3) . . ? B1 K1 H1 179.5(3) 2_666 . ? N8 Na1 N8 180.0 . 2_565 ? N8 Na1 N5 78.96(3) . . ? N8 Na1 N5 101.04(3) 2_565 . ? N8 Na1 N5 101.04(3) . 2_565 ? N8 Na1 N5 78.96(3) 2_565 2_565 ? N5 Na1 N5 180.0 . 2_565 ? N8 Na1 N2 80.69(3) . . ? N8 Na1 N2 99.31(3) 2_565 . ? N5 Na1 N2 77.52(3) . . ? N5 Na1 N2 102.48(3) 2_565 . ? N8 Na1 N2 99.31(3) . 2_565 ? N8 Na1 N2 80.69(3) 2_565 2_565 ? N5 Na1 N2 102.48(3) . 2_565 ? N5 Na1 N2 77.52(3) 2_565 2_565 ? N2 Na1 N2 180.0 . 2_565 ? C1 S1 K1 113.52(4) . . ? C4 S2 K1 112.07(3) . . ? C7 S3 K1 113.47(4) . . ? C1 N1 N2 110.57(8) . . ? C1 N1 B1 127.48(8) . . ? N2 N1 B1 121.58(8) . . ? C2 N2 N1 105.04(8) . . ? C2 N2 Na1 134.61(7) . . ? N1 N2 Na1 119.33(6) . . ? C2 N3 C1 107.68(9) . . ? C2 N3 C3 126.63(9) . . ? C1 N3 C3 125.66(9) . . ? C4 N4 N5 110.76(8) . . ? C4 N4 B1 128.25(8) . . ? N5 N4 B1 120.74(8) . . ? C5 N5 N4 105.18(8) . . ? C5 N5 Na1 134.72(7) . . ? N4 N5 Na1 120.08(6) . . ? C5 N6 C4 107.84(9) . . ? C5 N6 C6 127.00(9) . . ? C4 N6 C6 125.13(9) . . ? C7 N7 N8 110.61(8) . . ? C7 N7 B1 127.63(8) . . ? N8 N7 B1 121.53(8) . . ? C8 N8 N7 105.07(8) . . ? C8 N8 Na1 135.25(7) . . ? N7 N8 Na1 119.63(6) . . ? C8 N9 C7 107.60(9) . . ? C8 N9 C9 126.25(9) . . ? C7 N9 C9 126.08(9) . . ? N1 C1 N3 104.99(9) . . ? N1 C1 S1 130.27(8) . . ? N3 C1 S1 124.73(8) . . ? N7 B1 N4 110.42(8) . . ? N7 B1 N1 111.60(8) . . ? N4 B1 N1 109.22(8) . . ? N7 B1 K1 109.00(6) . . ? N4 B1 K1 108.98(6) . . ? N1 B1 K1 107.54(6) . . ? N7 B1 H1 108.3(7) . . ? N4 B1 H1 108.6(7) . . ? N1 B1 H1 108.7(7) . . ? K1 B1 H1 1.2(7) . . ? N2 C2 N3 111.71(9) . . ? N2 C2 H2 125.7(9) . . ? N3 C2 H2 122.6(9) . . ? N3 C3 H3B 109.1(9) . . ? N3 C3 H3C 107.4(10) . . ? H3B C3 H3C 108.9(13) . . ? N3 C3 H3A 110.6(9) . . ? H3B C3 H3A 109.3(13) . . ? H3C C3 H3A 111.6(13) . . ? N4 C4 N6 104.78(8) . . ? N4 C4 S2 130.65(8) . . ? N6 C4 S2 124.57(8) . . ? N5 C5 N6 111.45(9) . . ? N5 C5 H5 123.4(10) . . ? N6 C5 H5 125.1(10) . . ? N6 C6 H6B 109.1(10) . . ? N6 C6 H6C 108.1(10) . . ? H6B C6 H6C 112.2(14) . . ? N6 C6 H6A 109.6(10) . . ? H6B C6 H6A 109.2(14) . . ? H6C C6 H6A 108.6(14) . . ? N7 C7 N9 105.07(8) . . ? N7 C7 S3 130.08(8) . . ? N9 C7 S3 124.84(8) . . ? N8 C8 N9 111.65(9) . . ? N8 C8 H8 125.5(9) . . ? N9 C8 H8 122.8(9) . . ? N9 C9 H9B 109.3(10) . . ? N9 C9 H9A 109.9(10) . . ? H9B C9 H9A 108.1(14) . . ? N9 C9 H9C 109.8(10) . . ? H9B C9 H9C 109.7(13) . . ? H9A C9 H9C 110.0(13) . . ? C10 N10 C11 120.96(12) . . ? C10 N10 C12 122.55(13) . . ? C11 N10 C12 116.44(11) . . ? O1 C10 N10 125.47(14) . . ? O1 C10 H10 121.3(11) . . ? N10 C10 H10 113.3(11) . . ? N10 C11 H11B 111.2(9) . . ? N10 C11 H11C 110.2(10) . . ? H11B C11 H11C 108.5(13) . . ? N10 C11 H11A 110.7(11) . . ? H11B C11 H11A 109.0(14) . . ? H11C C11 H11A 107.2(15) . . ? N10 C12 H12B 108.4(11) . . ? N10 C12 H12C 106.9(12) . . ? H12B C12 H12C 109.7(16) . . ? N10 C12 H12A 110.7(12) . . ? H12B C12 H12A 110.4(16) . . ? H12C C12 H12A 110.7(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.291 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 952328' ####################################################################### # # 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_compound3a _vrf_PLAT601_compound3a ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 464 A**3 RESPONSE: The crystal includes a highly disordered solvent on a threefold axis, which could not be determined reliably as the used solvent toluene or thf. It was treated with the SQUEEZE procedure of Olex2 program (Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., J. Appl. Cryst. (2009). 42, 339-341.) The sum formular and further calculations disregard this electron density. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 B2 K N18 Na S6' _chemical_formula_sum 'C18 H26 B2 K N18 Na S6' _chemical_formula_weight 770.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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' Na Na 0.0362 0.0249 '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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P -3 1 c' _symmetry_space_group_name_Hall '-P 3 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 13.0298(7) _cell_length_b 13.0298(7) _cell_length_c 14.0697(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2068.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9913 _cell_measurement_theta_min 2.897 _cell_measurement_theta_max 27.290 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8139 _exptl_absorpt_correction_T_max 0.9248 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device 'Bruker KAPPA APEX II ' _diffrn_radiation_source 'fine focus sealed tube ' _diffrn_radiation_monochromator 'graphite monochromator ' _diffrn_measurement_device_type 'four three circle diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1560 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.34 _reflns_number_total 1560 _reflns_number_gt 1442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 2.1 (Crystal Impact, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; The crystal includes a highly disordered solvent on a threefold axis, which could not be determined reliably as the used solvent toluene or thf. It was treated with the SQUEEZE procedure of Olex2 program (Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., J. Appl. Cryst. (2009). 42, 339-341.) The sum formular and further calculations disregard this electron density. Unit cell: (13.0298, 13.0298, 14.0697, 90, 90, 120) Space group: P -3 1 c (No. 163) Systematic absences: 1886 Systematic absences not included in following: Centric reflections: 45732 Resolution range: 8.80276 0.773781 Completeness in resolution range: 28.9994 Completeness with d_max=infinity: 28.981 use_set_completion: False solvent_radius: 1.20 shrink_truncation_radius: 1.20 van der Waals radii: B C H K N Na S 2.00 1.70 1.09 2.75 1.55 2.27 1.80 Total solvent accessible volume / cell = 504.8 A**3 [24.4%] Total electron count / cell = 10.0 gridding: (72,72,80) Void #Grid points Vol/A**3 Vol/% Centre of mass (frac) Eigenvectors (frac) 1 101210 504.8 24.4 ( 0.000, 0.000,-0.987) 1 ( 0.708, 0.707,-0.000) 2 (-0.707, 0.708, 0.000) 3 ( 0.000,-0.000, 1.000) Void Vol/A**3 #Electrons 1 504.8 10.0 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^)+(0.0408P)^2^+6.7554P] 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 1560 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 K1 K 0.6667 0.3333 0.7500 0.0330(4) Uani 1 6 d S . . S1 S 0.90128(8) 0.52373(8) 0.62933(7) 0.0308(3) Uani 1 1 d . . . Na1 Na 0.6667 0.3333 0.2500 0.0476(11) Uani 1 6 d S . . N1 N 0.7778(2) 0.4467(2) 0.46058(18) 0.0209(5) Uani 1 1 d . . . N2 N 0.7889(3) 0.4821(3) 0.3670(2) 0.0319(7) Uani 1 1 d . . . N3 N 0.9396(2) 0.6139(3) 0.4500(2) 0.0329(7) Uani 1 1 d . . . B1 B 0.6667 0.3333 0.4963(4) 0.0190(11) Uani 1 3 d S . . H1 H 0.6667 0.3333 0.5673 0.023 Uiso 1 3 calc SR . . C1 C 0.8706(3) 0.5263(3) 0.5126(2) 0.0227(6) Uani 1 1 d . . . C2 C 0.8881(3) 0.5832(4) 0.3638(3) 0.0378(9) Uani 1 1 d . . . H2 H 0.9199 0.6292 0.3079 0.045 Uiso 1 1 calc R . . C3 C 1.0531(3) 0.7193(4) 0.4699(4) 0.0496(12) Uani 1 1 d . . . H3A H 1.0396 0.7804 0.4978 0.074 Uiso 1 1 calc R . . H3B H 1.0980 0.7491 0.4107 0.074 Uiso 1 1 calc R . . H3C H 1.0981 0.6993 0.5146 0.074 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 K1 0.0398(7) 0.0398(7) 0.0194(8) 0.000 0.000 0.0199(3) S1 0.0214(4) 0.0303(5) 0.0387(5) -0.0059(3) -0.0107(3) 0.0114(3) Na1 0.0649(17) 0.0649(17) 0.0130(15) 0.000 0.000 0.0324(9) N1 0.0190(12) 0.0200(13) 0.0215(12) 0.0026(10) 0.0042(10) 0.0080(10) N2 0.0314(16) 0.0366(17) 0.0258(14) 0.0113(12) 0.0086(12) 0.0157(13) N3 0.0168(13) 0.0246(15) 0.0548(19) 0.0096(13) 0.0077(13) 0.0084(12) B1 0.0196(16) 0.0196(16) 0.018(2) 0.000 0.000 0.0098(8) C1 0.0154(14) 0.0178(14) 0.0370(17) -0.0015(12) 0.0010(12) 0.0099(12) C2 0.0297(18) 0.041(2) 0.041(2) 0.0193(17) 0.0141(16) 0.0159(17) C3 0.0151(17) 0.0276(19) 0.094(4) 0.010(2) 0.0042(19) 0.0018(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 K1 S1 3.2860(9) 6_556 ? K1 S1 3.2860(9) 3_665 ? K1 S1 3.2860(9) 5_656 ? K1 S1 3.2860(9) 2_655 ? K1 S1 3.2860(9) 4_666 ? K1 S1 3.2860(9) . ? K1 B1 3.570(6) . ? K1 B1 3.570(6) 4_666 ? K1 H1 2.570 . ? S1 C1 1.695(3) . ? Na1 N2 2.432(3) 6 ? Na1 N2 2.432(3) 3_665 ? Na1 N2 2.432(3) 4_665 ? Na1 N2 2.432(3) . ? Na1 N2 2.432(3) 2_655 ? Na1 N2 2.432(3) 5_655 ? N1 C1 1.349(4) . ? N1 N2 1.379(4) . ? N1 B1 1.546(3) . ? N2 C2 1.307(5) . ? N3 C2 1.346(5) . ? N3 C1 1.364(4) . ? N3 C3 1.456(5) . ? B1 N1 1.546(3) 3_665 ? B1 N1 1.546(3) 2_655 ? B1 H1 1.0000 . ? C2 H2 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 K1 S1 98.34(3) 6_556 3_665 ? S1 K1 S1 95.72(2) 6_556 5_656 ? S1 K1 S1 162.53(3) 3_665 5_656 ? S1 K1 S1 162.53(3) 6_556 2_655 ? S1 K1 S1 95.72(2) 3_665 2_655 ? S1 K1 S1 72.65(3) 5_656 2_655 ? S1 K1 S1 95.72(2) 6_556 4_666 ? S1 K1 S1 72.65(3) 3_665 4_666 ? S1 K1 S1 95.72(2) 5_656 4_666 ? S1 K1 S1 98.34(3) 2_655 4_666 ? S1 K1 S1 72.65(3) 6_556 . ? S1 K1 S1 95.72(2) 3_665 . ? S1 K1 S1 98.34(3) 5_656 . ? S1 K1 S1 95.72(2) 2_655 . ? S1 K1 S1 162.53(3) 4_666 . ? S1 K1 B1 121.108(15) 6_556 . ? S1 K1 B1 58.892(15) 3_665 . ? S1 K1 B1 121.108(15) 5_656 . ? S1 K1 B1 58.892(15) 2_655 . ? S1 K1 B1 121.108(15) 4_666 . ? S1 K1 B1 58.892(15) . . ? S1 K1 B1 58.892(15) 6_556 4_666 ? S1 K1 B1 121.108(15) 3_665 4_666 ? S1 K1 B1 58.892(15) 5_656 4_666 ? S1 K1 B1 121.108(15) 2_655 4_666 ? S1 K1 B1 58.892(15) 4_666 4_666 ? S1 K1 B1 121.109(15) . 4_666 ? B1 K1 B1 180.000(1) . 4_666 ? H1 K1 S1 121.1 . 6_556 ? H1 K1 S1 58.9 . 3_665 ? H1 K1 S1 121.1 . 5_656 ? H1 K1 S1 58.9 . 2_655 ? H1 K1 S1 121.1 . 4_666 ? H1 K1 S1 58.9 . . ? H1 K1 B1 0.0 . . ? H1 K1 B1 180.0 . 4_666 ? C1 S1 K1 112.08(11) . . ? N2 Na1 N2 92.70(14) 6 3_665 ? N2 Na1 N2 79.23(10) 6 4_665 ? N2 Na1 N2 110.92(14) 3_665 4_665 ? N2 Na1 N2 110.92(14) 6 . ? N2 Na1 N2 79.23(10) 3_665 . ? N2 Na1 N2 165.84(15) 4_665 . ? N2 Na1 N2 165.84(15) 6 2_655 ? N2 Na1 N2 79.23(10) 3_665 2_655 ? N2 Na1 N2 92.70(14) 4_665 2_655 ? N2 Na1 N2 79.23(10) . 2_655 ? N2 Na1 N2 79.23(10) 6 5_655 ? N2 Na1 N2 165.84(15) 3_665 5_655 ? N2 Na1 N2 79.23(10) 4_665 5_655 ? N2 Na1 N2 92.70(14) . 5_655 ? N2 Na1 N2 110.92(14) 2_655 5_655 ? C1 N1 N2 110.9(3) . . ? C1 N1 B1 127.6(3) . . ? N2 N1 B1 121.4(3) . . ? C2 N2 N1 104.8(3) . . ? C2 N2 Na1 134.8(3) . . ? N1 N2 Na1 117.5(2) . . ? C2 N3 C1 108.1(3) . . ? C2 N3 C3 125.0(3) . . ? C1 N3 C3 126.8(4) . . ? N1 B1 N1 110.0(2) . 3_665 ? N1 B1 N1 110.0(2) . 2_655 ? N1 B1 N1 110.0(2) 3_665 2_655 ? N1 B1 K1 108.9(2) . . ? N1 B1 K1 108.9(2) 3_665 . ? N1 B1 K1 108.9(2) 2_655 . ? N1 B1 H1 108.9 . . ? N1 B1 H1 108.9 3_665 . ? N1 B1 H1 108.9 2_655 . ? K1 B1 H1 0.0 . . ? N1 C1 N3 104.8(3) . . ? N1 C1 S1 129.8(2) . . ? N3 C1 S1 125.4(3) . . ? N2 C2 N3 111.4(3) . . ? N2 C2 H2 124.3 . . ? N3 C2 H2 124.3 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.34 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.523 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 952329' ####################################################################### # # 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_compound5 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.500 0.000 0.520 290 66 ' ' _platon_squeeze_details ; Highly disordered acetone near an inversion center was squeezed one void / 290 A*3 / 66 e- => two acetone / unit cell ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 B2 Bi2 Cl4 N18 S6, 2(C3 H6 O)(squeezed)' _chemical_formula_sum 'C24 H38 B2 Bi2 Cl4 N18 O2 S6' _chemical_formula_weight 1384.46 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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' _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 10.324(4) _cell_length_b 11.303(6) _cell_length_c 11.545(6) _cell_angle_alpha 94.49(4) _cell_angle_beta 102.35(5) _cell_angle_gamma 114.39(3) _cell_volume 1177.3(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 5.939 _cell_measurement_theta_max 19.278 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.953 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 8.004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3268 _exptl_absorpt_correction_T_max 0.8563 _exptl_absorpt_process_details 'SADABS-2008/2 - Bruker AXS area detector scaling and absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24943 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5380 _reflns_number_gt 4698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Highly disordered acetone was squeezed but left in the sum formular for further calculations. H(1B) was refined isotropically. 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^)+(0.0263P)^2^+2.4375P] 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 5380 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0687 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.301499(19) 0.375249(18) 0.420151(15) 0.01922(7) Uani 1 1 d . . . Cl1 Cl 0.10098(14) 0.22722(13) 0.52731(11) 0.0286(3) Uani 1 1 d . . . Cl2 Cl 0.42640(13) 0.66304(13) 0.52472(11) 0.0260(3) Uani 1 1 d . . . S1 S 0.05127(13) 0.37685(12) 0.29767(10) 0.0210(2) Uani 1 1 d . . . S2 S 0.25466(13) 0.16691(12) 0.25904(10) 0.0214(2) Uani 1 1 d . . . S3 S 0.44850(13) 0.54187(12) 0.27294(10) 0.0212(2) Uani 1 1 d . . . N1 N 0.1386(4) 0.4447(4) 0.0905(3) 0.0187(8) Uani 1 1 d . . . N2 N 0.1813(4) 0.5543(4) 0.0347(4) 0.0227(9) Uani 1 1 d . . . N3 N 0.1326(4) 0.6032(4) 0.2041(4) 0.0216(9) Uani 1 1 d . . . N4 N 0.0575(4) 0.1973(4) 0.0732(3) 0.0195(8) Uani 1 1 d . . . N5 N -0.0929(4) 0.1386(4) 0.0158(4) 0.0212(9) Uani 1 1 d . . . N6 N -0.0458(4) 0.0363(4) 0.1644(4) 0.0206(8) Uani 1 1 d . . . N7 N 0.3167(4) 0.3532(4) 0.0623(4) 0.0217(9) Uani 1 1 d . . . N8 N 0.3546(4) 0.2798(4) -0.0149(4) 0.0229(9) Uani 1 1 d . . . N9 N 0.5492(4) 0.4100(4) 0.1358(4) 0.0233(9) Uani 1 1 d . . . B1 B 0.1518(6) 0.3245(5) 0.0308(5) 0.0200(11) Uani 1 1 d . . . H1B H 0.109(5) 0.309(4) -0.067(4) 0.010(11) Uiso 1 1 d . . . C1 C 0.1088(5) 0.4755(5) 0.1933(4) 0.0194(10) Uani 1 1 d . . . C2 C 0.1757(5) 0.6467(5) 0.1063(5) 0.0249(11) Uani 1 1 d . . . H2 H 0.1991 0.7337 0.0915 0.030 Uiso 1 1 calc R . . C3 C 0.1170(6) 0.6791(5) 0.3041(5) 0.0297(12) Uani 1 1 d . . . H3A H 0.0134 0.6405 0.3060 0.045 Uiso 1 1 calc R . . H3B H 0.1482 0.7710 0.2931 0.045 Uiso 1 1 calc R . . H3C H 0.1787 0.6766 0.3803 0.045 Uiso 1 1 calc R . . C4 C 0.0863(5) 0.1359(5) 0.1638(4) 0.0208(10) Uani 1 1 d . . . C5 C -0.1512(5) 0.0431(5) 0.0735(4) 0.0226(10) Uani 1 1 d . . . H5 H -0.2538 -0.0144 0.0546 0.027 Uiso 1 1 calc R . . C6 C -0.0687(6) -0.0541(5) 0.2514(5) 0.0265(11) Uani 1 1 d . . . H6A H -0.1737 -0.1160 0.2321 0.040 Uiso 1 1 calc R . . H6B H -0.0371 -0.0028 0.3332 0.040 Uiso 1 1 calc R . . H6C H -0.0106 -0.1034 0.2468 0.040 Uiso 1 1 calc R . . C7 C 0.4343(5) 0.4312(5) 0.1544(4) 0.0190(10) Uani 1 1 d . . . C8 C 0.4955(6) 0.3174(5) 0.0343(5) 0.0272(11) Uani 1 1 d . . . H8 H 0.5533 0.2835 0.0022 0.033 Uiso 1 1 calc R . . C9 C 0.7013(5) 0.4743(6) 0.2142(5) 0.0310(12) Uani 1 1 d . . . H9A H 0.7365 0.5705 0.2277 0.046 Uiso 1 1 calc R . . H9B H 0.7653 0.4509 0.1755 0.046 Uiso 1 1 calc R . . H9C H 0.7034 0.4445 0.2918 0.046 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 0.01669(10) 0.02557(11) 0.01607(9) 0.00346(7) 0.00472(7) 0.00991(8) Cl1 0.0293(7) 0.0326(7) 0.0247(6) 0.0089(5) 0.0133(5) 0.0109(6) Cl2 0.0232(6) 0.0336(7) 0.0239(6) 0.0014(5) 0.0039(5) 0.0169(6) S1 0.0163(6) 0.0285(6) 0.0200(6) 0.0048(5) 0.0058(5) 0.0111(5) S2 0.0204(6) 0.0268(6) 0.0190(6) 0.0033(5) 0.0032(5) 0.0136(5) S3 0.0183(6) 0.0264(6) 0.0180(6) 0.0020(5) 0.0051(5) 0.0095(5) N1 0.0159(19) 0.022(2) 0.022(2) 0.0099(16) 0.0074(16) 0.0095(17) N2 0.018(2) 0.025(2) 0.026(2) 0.0076(18) 0.0063(17) 0.0100(18) N3 0.017(2) 0.023(2) 0.026(2) 0.0037(17) 0.0038(17) 0.0119(18) N4 0.015(2) 0.025(2) 0.0178(19) 0.0022(16) 0.0034(16) 0.0089(17) N5 0.019(2) 0.022(2) 0.020(2) 0.0002(16) 0.0019(17) 0.0089(18) N6 0.021(2) 0.018(2) 0.022(2) 0.0007(16) 0.0044(17) 0.0083(18) N7 0.022(2) 0.025(2) 0.020(2) 0.0058(17) 0.0096(17) 0.0090(18) N8 0.019(2) 0.029(2) 0.019(2) 0.0002(17) 0.0088(17) 0.0075(19) N9 0.016(2) 0.031(2) 0.019(2) 0.0002(17) 0.0060(16) 0.0068(19) B1 0.018(3) 0.025(3) 0.015(3) 0.004(2) 0.002(2) 0.008(2) C1 0.012(2) 0.027(3) 0.022(2) 0.0071(19) 0.0054(18) 0.010(2) C2 0.020(3) 0.026(3) 0.029(3) 0.009(2) 0.003(2) 0.011(2) C3 0.031(3) 0.032(3) 0.029(3) 0.001(2) 0.006(2) 0.018(3) C4 0.023(3) 0.025(3) 0.017(2) 0.0024(19) 0.0041(19) 0.014(2) C5 0.018(2) 0.026(3) 0.022(2) 0.001(2) 0.003(2) 0.009(2) C6 0.029(3) 0.023(3) 0.025(3) 0.006(2) 0.005(2) 0.011(2) C7 0.015(2) 0.019(2) 0.016(2) 0.0029(18) 0.0034(18) 0.001(2) C8 0.023(3) 0.035(3) 0.025(3) 0.001(2) 0.013(2) 0.013(2) C9 0.013(2) 0.044(3) 0.028(3) -0.003(2) 0.006(2) 0.007(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 S1 2.6746(18) . ? Bi1 Cl1 2.6784(18) . ? Bi1 S2 2.688(2) . ? Bi1 S3 2.8252(19) . ? Bi1 Cl2 2.9608(17) 2_666 ? Bi1 Cl2 2.993(2) . ? Cl2 Bi1 2.9608(17) 2_666 ? S1 C1 1.737(5) . ? S2 C4 1.724(5) . ? S3 C7 1.719(5) . ? N1 C1 1.343(6) . ? N1 N2 1.392(6) . ? N1 B1 1.545(7) . ? N2 C2 1.308(7) . ? N3 C1 1.351(6) . ? N3 C2 1.354(7) . ? N3 C3 1.462(6) . ? N4 C4 1.347(6) . ? N4 N5 1.389(5) . ? N4 B1 1.553(7) . ? N5 C5 1.311(7) . ? N6 C4 1.365(6) . ? N6 C5 1.372(6) . ? N6 C6 1.474(6) . ? N7 C7 1.342(6) . ? N7 N8 1.391(6) . ? N7 B1 1.548(7) . ? N8 C8 1.310(6) . ? N9 C8 1.352(6) . ? N9 C7 1.359(6) . ? N9 C9 1.469(6) . ? B1 H1B 1.09(4) . ? C2 H2 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Bi1 Cl1 76.53(5) . . ? S1 Bi1 S2 90.83(6) . . ? Cl1 Bi1 S2 93.33(6) . . ? S1 Bi1 S3 88.14(5) . . ? Cl1 Bi1 S3 164.60(4) . . ? S2 Bi1 S3 88.24(6) . . ? S1 Bi1 Cl2 161.17(4) . 2_666 ? Cl1 Bi1 Cl2 112.77(5) . 2_666 ? S2 Bi1 Cl2 72.75(6) . 2_666 ? S3 Bi1 Cl2 82.33(5) . 2_666 ? S1 Bi1 Cl2 90.74(6) . . ? Cl1 Bi1 Cl2 111.29(5) . . ? S2 Bi1 Cl2 154.99(4) . . ? S3 Bi1 Cl2 66.87(5) . . ? Cl2 Bi1 Cl2 100.29(5) 2_666 . ? Bi1 Cl2 Bi1 79.71(5) 2_666 . ? C1 S1 Bi1 102.61(16) . . ? C4 S2 Bi1 101.09(17) . . ? C7 S3 Bi1 102.77(17) . . ? C1 N1 N2 109.6(4) . . ? C1 N1 B1 134.7(4) . . ? N2 N1 B1 115.3(4) . . ? C2 N2 N1 104.7(4) . . ? C1 N3 C2 107.0(4) . . ? C1 N3 C3 125.8(4) . . ? C2 N3 C3 127.2(4) . . ? C4 N4 N5 110.3(4) . . ? C4 N4 B1 133.8(4) . . ? N5 N4 B1 115.5(4) . . ? C5 N5 N4 104.9(4) . . ? C4 N6 C5 106.4(4) . . ? C4 N6 C6 125.8(4) . . ? C5 N6 C6 127.7(4) . . ? C7 N7 N8 110.6(4) . . ? C7 N7 B1 133.2(4) . . ? N8 N7 B1 116.0(4) . . ? C8 N8 N7 103.9(4) . . ? C8 N9 C7 106.9(4) . . ? C8 N9 C9 127.4(4) . . ? C7 N9 C9 125.7(4) . . ? N1 B1 N7 108.9(4) . . ? N1 B1 N4 110.3(4) . . ? N7 B1 N4 111.5(4) . . ? N1 B1 H1B 109(2) . . ? N7 B1 H1B 109(2) . . ? N4 B1 H1B 107(2) . . ? N1 C1 N3 107.0(4) . . ? N1 C1 S1 129.0(4) . . ? N3 C1 S1 124.0(4) . . ? N2 C2 N3 111.7(4) . . ? N2 C2 H2 124.1 . . ? N3 C2 H2 124.1 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 N6 106.7(4) . . ? N4 C4 S2 128.7(4) . . ? N6 C4 S2 124.6(4) . . ? N5 C5 N6 111.7(4) . . ? N5 C5 H5 124.1 . . ? N6 C5 H5 124.1 . . ? N6 C6 H6A 109.5 . . ? N6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 N9 106.2(4) . . ? N7 C7 S3 129.6(4) . . ? N9 C7 S3 124.2(3) . . ? N8 C8 N9 112.4(4) . . ? N8 C8 H8 123.8 . . ? N9 C8 H8 123.8 . . ? N9 C9 H9A 109.5 . . ? N9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.156 _refine_diff_density_min -1.275 _refine_diff_density_rms 0.161 _database_code_depnum_ccdc_archive 'CCDC 952330' ####################################################################### # # 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_compound6 _vrf_PLAT601_compound6 ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 504 A**3 RESPONSE: The crystal includes a highly disordered solvent which could not be determined reliably as the used solvent. It was treated with the SQUEEZE procedure of Olex2 program (Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., J. Appl. Cryst. (2009) 42, 339-341.) The sum formular and further calculations disregard this electron density. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H13 B Bi Cl2 N9 S3' _chemical_formula_sum 'C9 H13 B Bi Cl2 N9 S3' _chemical_formula_weight 634.15 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' B B 0.0013 0.0007 '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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 30.8530(12) _cell_length_b 30.8530(12) _cell_length_c 9.6827(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9217.0(7) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9971 _cell_measurement_theta_min 2.570 _cell_measurement_theta_max 23.490 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4800 _exptl_absorpt_coefficient_mu 8.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2739 _exptl_absorpt_correction_T_max 0.8472 _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device 'Bruker KAPPA APEX II ' _diffrn_radiation_source 'fine focus sealed tube ' _diffrn_radiation_monochromator 'graphite monochromator ' _diffrn_measurement_device_type 'four three circle diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4109 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.12 _reflns_number_total 4109 _reflns_number_gt 3247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 2.1 (Crystal Impact, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; The crystal includes a highly disordered solvent which could not be determined reliably as the used solvent. It was treated with the SQUEEZE procedure of Olex2 program (Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., J. Appl. Cryst. (2009). 42, 339-341.) The sum formular and further calculations disregard this electron density. Total solvent accessible volume / cell = 2053.0 Ang^3 [22.3%] Total electron count / cell = 302.4 gridding: (160,160,48) Void #Grid points Vol/A^3 Vol/% Centre of mass (frac) Eigenvectors (frac) 1 68424 513.2 5.6 ( 0.000, 0.250,-0.899) 1 ( 1.000,-0.024, 0.018) 2 ( 0.024, 1.000,-0.000) 3 (-0.018, 0.000, 1.000) 2 68424 513.2 5.6 (-0.000, 0.750,-0.436) 1 ( 0.947,-0.320,-0.004) 2 ( 0.320, 0.947,-0.000) 3 ( 0.004,-0.001, 1.000) 3 68424 513.2 5.6 ( 0.500, 0.250,-0.837) 1 ( 0.962, 0.272, 0.005) 2 (-0.272, 0.962,-0.000) 3 (-0.005,-0.001, 1.000) 4 68424 513.2 5.6 ( 0.500, 0.750,-0.711) 1 ( 0.911, 0.413, 0.010) 2 (-0.413, 0.911,-0.000) 3 (-0.009,-0.004, 1.000) Void Vol/Ang^3 #Electrons 1 513.2 75.6 2 513.2 75.6 3 513.2 75.6 4 513.2 75.6 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^)+(0.0340P)^2^+1.6367P] 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 4109 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.635989(5) 0.516002(6) 0.822752(17) 0.02061(7) Uani 1 1 d . . . Cl1 Cl 0.69272(4) 0.44807(4) 0.74006(13) 0.0317(3) Uani 1 1 d . . . Cl2 Cl 0.59859(4) 0.46730(5) 1.02076(13) 0.0367(3) Uani 1 1 d . . . S1 S 0.57154(4) 0.56747(4) 0.90502(13) 0.0289(3) Uani 1 1 d . . . S2 S 0.66788(4) 0.58128(4) 0.65465(12) 0.0246(3) Uani 1 1 d . . . S3 S 0.58765(4) 0.48608(4) 0.61063(13) 0.0281(3) Uani 1 1 d . . . N1 N 0.57514(13) 0.62240(14) 0.6808(5) 0.0342(11) Uani 1 1 d . . . N2 N 0.58960(16) 0.66353(16) 0.6490(7) 0.0520(14) Uani 1 1 d . . . N3 N 0.60154(14) 0.64847(15) 0.8674(6) 0.0399(12) Uani 1 1 d . . . N4 N 0.59886(13) 0.57912(15) 0.4723(4) 0.0306(10) Uani 1 1 d . . . N5 N 0.59044(14) 0.56679(17) 0.3381(4) 0.0414(12) Uani 1 1 d . . . N6 N 0.65837(13) 0.55493(14) 0.3897(4) 0.0271(10) Uani 1 1 d . . . N7 N 0.53179(13) 0.55632(15) 0.6062(4) 0.0298(10) Uani 1 1 d . . . N8 N 0.48987(13) 0.56641(16) 0.6472(5) 0.0367(11) Uani 1 1 d . . . N9 N 0.50603(13) 0.49913(15) 0.7044(4) 0.0318(11) Uani 1 1 d . . . B1 B 0.5593(2) 0.5949(2) 0.5551(7) 0.0367(16) Uani 1 1 d . . . H1 H 0.5410 0.6136 0.4941 0.044 Uiso 1 1 calc R . . C1 C 0.58271(15) 0.61341(17) 0.8125(6) 0.0318(13) Uani 1 1 d . . . C2 C 0.6054(2) 0.6775(2) 0.7649(9) 0.0552(18) Uani 1 1 d . . . H2 H 0.6183 0.7053 0.7761 0.066 Uiso 1 1 calc R . . C3 C 0.6156(2) 0.6545(2) 1.0098(7) 0.0543(18) Uani 1 1 d . . . H3A H 0.6409 0.6361 1.0279 0.081 Uiso 1 1 calc R . . H3B H 0.5921 0.6465 1.0726 0.081 Uiso 1 1 calc R . . H3C H 0.6234 0.6849 1.0246 0.081 Uiso 1 1 calc R . . C4 C 0.63997(16) 0.57194(16) 0.5049(5) 0.0277(12) Uani 1 1 d . . . C5 C 0.62730(17) 0.5526(2) 0.2942(6) 0.0386(14) Uani 1 1 d . . . H5 H 0.6318 0.5416 0.2036 0.046 Uiso 1 1 calc R . . C6 C 0.70358(16) 0.54125(18) 0.3773(6) 0.0309(12) Uani 1 1 d . . . H6A H 0.7226 0.5646 0.4096 0.046 Uiso 1 1 calc R . . H6B H 0.7101 0.5347 0.2804 0.046 Uiso 1 1 calc R . . H6C H 0.7083 0.5153 0.4335 0.046 Uiso 1 1 calc R . . C7 C 0.54146(16) 0.51571(17) 0.6409(5) 0.0274(12) Uani 1 1 d . . . C8 C 0.47585(17) 0.53140(19) 0.7051(5) 0.0338(13) Uani 1 1 d . . . H8 H 0.4477 0.5285 0.7439 0.041 Uiso 1 1 calc R . . C9 C 0.50274(19) 0.45707(19) 0.7696(6) 0.0417(15) Uani 1 1 d . . . H9A H 0.5266 0.4534 0.8354 0.063 Uiso 1 1 calc R . . H9B H 0.5044 0.4344 0.6990 0.063 Uiso 1 1 calc R . . H9C H 0.4750 0.4549 0.8184 0.063 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 0.01928(11) 0.02628(11) 0.01626(10) -0.00255(8) 0.00119(8) -0.00146(8) Cl1 0.0349(7) 0.0367(7) 0.0235(7) -0.0059(6) -0.0026(6) 0.0097(6) Cl2 0.0358(7) 0.0485(8) 0.0258(7) 0.0062(6) 0.0042(6) -0.0097(6) S1 0.0229(6) 0.0370(7) 0.0268(7) -0.0063(6) 0.0059(6) -0.0012(6) S2 0.0204(6) 0.0333(7) 0.0201(7) -0.0002(5) 0.0001(5) -0.0038(5) S3 0.0229(6) 0.0376(7) 0.0237(7) -0.0082(6) 0.0006(5) -0.0051(6) N1 0.022(2) 0.036(3) 0.045(3) 0.006(2) 0.006(2) 0.0028(19) N2 0.036(3) 0.037(3) 0.083(4) 0.018(3) 0.000(3) 0.000(2) N3 0.029(3) 0.035(3) 0.056(3) -0.008(3) 0.003(2) -0.002(2) N4 0.020(2) 0.050(3) 0.022(2) 0.008(2) -0.0022(18) -0.002(2) N5 0.026(2) 0.076(4) 0.022(3) 0.010(2) -0.002(2) -0.006(2) N6 0.023(2) 0.043(3) 0.016(2) 0.0000(19) 0.0008(18) -0.008(2) N7 0.019(2) 0.047(3) 0.024(2) 0.000(2) 0.0033(18) -0.002(2) N8 0.019(2) 0.055(3) 0.036(3) 0.001(2) 0.002(2) 0.001(2) N9 0.019(2) 0.054(3) 0.022(2) -0.005(2) -0.0006(19) -0.009(2) B1 0.025(3) 0.047(4) 0.039(4) 0.010(3) -0.001(3) 0.003(3) C1 0.017(3) 0.038(3) 0.041(4) -0.004(3) 0.007(2) 0.002(2) C2 0.038(4) 0.038(4) 0.089(6) -0.007(4) 0.000(4) 0.000(3) C3 0.047(4) 0.055(4) 0.061(5) -0.029(4) 0.012(3) -0.018(3) C4 0.024(3) 0.034(3) 0.024(3) 0.000(2) 0.001(2) -0.007(2) C5 0.030(3) 0.065(4) 0.021(3) 0.001(3) -0.005(2) -0.010(3) C6 0.023(3) 0.042(3) 0.028(3) -0.001(3) 0.005(2) -0.005(2) C7 0.023(3) 0.042(3) 0.017(3) -0.004(2) -0.006(2) -0.008(2) C8 0.019(3) 0.058(4) 0.024(3) -0.005(3) 0.002(2) -0.007(3) C9 0.036(3) 0.058(4) 0.032(3) 0.004(3) -0.003(3) -0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 S1 2.6664(13) . ? Bi1 Cl2 2.6954(13) . ? Bi1 S3 2.7009(12) . ? Bi1 S2 2.7701(13) . ? Bi1 Cl1 2.8135(12) 4_565 ? Bi1 Cl1 2.8455(12) . ? Cl1 Bi1 2.8134(12) 6_544 ? S1 C1 1.712(6) . ? S2 C4 1.711(5) . ? S3 C7 1.718(5) . ? N1 C1 1.326(7) . ? N1 N2 1.380(6) . ? N1 B1 1.562(8) . ? N2 C2 1.298(9) . ? N3 C1 1.338(7) . ? N3 C2 1.343(9) . ? N3 C3 1.458(8) . ? N4 C4 1.325(6) . ? N4 N5 1.379(6) . ? N4 B1 1.539(7) . ? N5 C5 1.291(7) . ? N6 C5 1.334(6) . ? N6 C4 1.357(6) . ? N6 C6 1.462(6) . ? N7 C7 1.331(7) . ? N7 N8 1.388(6) . ? N7 B1 1.543(8) . ? N8 C8 1.292(7) . ? N9 C7 1.355(6) . ? N9 C8 1.363(7) . ? N9 C9 1.447(7) . ? B1 H1 1.0000 . ? C2 H2 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Bi1 Cl2 78.48(4) . . ? S1 Bi1 S3 91.09(4) . . ? Cl2 Bi1 S3 96.54(4) . . ? S1 Bi1 S2 90.43(4) . . ? Cl2 Bi1 S2 167.24(4) . . ? S3 Bi1 S2 89.87(4) . . ? S1 Bi1 Cl1 93.79(4) . 4_565 ? Cl2 Bi1 Cl1 97.72(4) . 4_565 ? S3 Bi1 Cl1 165.59(4) . 4_565 ? S2 Bi1 Cl1 76.55(4) . 4_565 ? S1 Bi1 Cl1 168.92(4) . . ? Cl2 Bi1 Cl1 93.03(4) . . ? S3 Bi1 Cl1 82.75(4) . . ? S2 Bi1 Cl1 98.73(4) . . ? Cl1 Bi1 Cl1 94.40(5) 4_565 . ? Bi1 Cl1 Bi1 160.38(5) 6_544 . ? C1 S1 Bi1 100.76(17) . . ? C4 S2 Bi1 101.36(17) . . ? C7 S3 Bi1 98.43(17) . . ? C1 N1 N2 110.5(5) . . ? C1 N1 B1 133.7(5) . . ? N2 N1 B1 115.3(5) . . ? C2 N2 N1 103.6(5) . . ? C1 N3 C2 106.6(5) . . ? C1 N3 C3 127.5(5) . . ? C2 N3 C3 126.0(5) . . ? C4 N4 N5 111.0(4) . . ? C4 N4 B1 133.5(5) . . ? N5 N4 B1 115.4(4) . . ? C5 N5 N4 103.8(4) . . ? C5 N6 C4 106.9(4) . . ? C5 N6 C6 127.8(4) . . ? C4 N6 C6 125.3(4) . . ? C7 N7 N8 110.3(4) . . ? C7 N7 B1 133.1(4) . . ? N8 N7 B1 115.6(4) . . ? C8 N8 N7 104.4(4) . . ? C7 N9 C8 106.1(5) . . ? C7 N9 C9 126.4(5) . . ? C8 N9 C9 127.2(4) . . ? N4 B1 N7 111.1(5) . . ? N4 B1 N1 109.2(4) . . ? N7 B1 N1 110.0(5) . . ? N4 B1 H1 108.8 . . ? N7 B1 H1 108.8 . . ? N1 B1 H1 108.8 . . ? N1 C1 N3 106.8(5) . . ? N1 C1 S1 129.9(4) . . ? N3 C1 S1 123.3(5) . . ? N2 C2 N3 112.5(6) . . ? N2 C2 H2 123.7 . . ? N3 C2 H2 123.7 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 N6 105.7(4) . . ? N4 C4 S2 130.9(4) . . ? N6 C4 S2 123.4(4) . . ? N5 C5 N6 112.7(5) . . ? N5 C5 H5 123.7 . . ? N6 C5 H5 123.7 . . ? N6 C6 H6A 109.5 . . ? N6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 N9 106.8(4) . . ? N7 C7 S3 130.1(4) . . ? N9 C7 S3 123.1(4) . . ? N8 C8 N9 112.3(5) . . ? N8 C8 H8 123.8 . . ? N9 C8 H8 123.8 . . ? N9 C9 H9A 109.5 . . ? N9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N9 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.533 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.114 _database_code_depnum_ccdc_archive 'CCDC 952331' ####################################################################### # # 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_compound7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 Bi Cl2 N12 S4, Cl' _chemical_formula_sum 'C12 H20 Bi Cl3 N12 S4' _chemical_formula_weight 775.97 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' Bi Bi -4.1077 10.2566 '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' 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' _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 17.7736(12) _cell_length_b 11.6737(12) _cell_length_c 14.194(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.552(7) _cell_angle_gamma 90.00 _cell_volume 2699.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 133 _cell_measurement_theta_min 3.776 _cell_measurement_theta_max 21.539 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.909 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 7.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2224 _exptl_absorpt_correction_T_max 0.6340 _exptl_absorpt_process_details 'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34793 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 29.99 _reflns_number_total 3915 _reflns_number_gt 3554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EVALCCD (Duisenberg,1998,Thesis.Utrecht University.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Hydrogens bonded to nitrogen atoms were refined isotropically. 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^)+(0.0078P)^2^+3.7750P] 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 3915 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0327 _refine_ls_wR_factor_gt 0.0314 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.5000 0.256813(7) 0.2500 0.00951(3) Uani 1 2 d S . . Cl1 Cl 0.33709(3) 0.26072(4) 0.15852(4) 0.02182(10) Uani 1 1 d . . . Cl2 Cl 0.5000 -0.24695(5) 0.2500 0.01979(12) Uani 1 2 d S . . S1 S 0.53099(3) 0.08188(4) 0.12918(4) 0.01516(9) Uani 1 1 d . . . S2 S 0.48425(3) 0.42680(4) 0.10408(4) 0.01794(10) Uani 1 1 d . . . N1 N 0.39882(10) -0.05684(14) 0.09423(13) 0.0175(3) Uani 1 1 d . . . H1 H 0.4218(15) -0.106(2) 0.142(2) 0.030(7) Uiso 1 1 d . . . N2 N 0.31749(10) -0.07176(15) 0.03098(14) 0.0216(4) Uani 1 1 d . . . N3 N 0.36997(9) 0.08124(13) -0.01297(12) 0.0147(3) Uani 1 1 d . . . N4 N 0.61173(11) 0.57036(14) 0.20676(13) 0.0188(3) Uani 1 1 d . . . H4 H 0.5841(17) 0.618(2) 0.227(2) 0.040(8) Uiso 1 1 d . . . N5 N 0.69279(11) 0.59179(14) 0.22740(14) 0.0222(4) Uani 1 1 d . . . N6 N 0.64780(10) 0.43533(13) 0.13212(13) 0.0179(3) Uani 1 1 d . . . C1 C 0.43193(11) 0.03436(15) 0.06934(15) 0.0144(4) Uani 1 1 d . . . C2 C 0.30203(12) 0.01457(17) -0.03271(16) 0.0196(4) Uani 1 1 d . . . H2A H 0.2499 0.0292 -0.0862 0.023 Uiso 1 1 calc R . . C3 C 0.37609(12) 0.18185(16) -0.07124(16) 0.0198(4) Uani 1 1 d . . . H3A H 0.3899 0.2493 -0.0264 0.030 Uiso 1 1 calc R . . H3B H 0.3234 0.1944 -0.1293 0.030 Uiso 1 1 calc R . . H3C H 0.4190 0.1691 -0.0969 0.030 Uiso 1 1 calc R . . C4 C 0.58268(12) 0.47718(15) 0.14889(15) 0.0157(4) Uani 1 1 d . . . C5 C 0.71241(13) 0.50780(17) 0.18104(17) 0.0225(4) Uani 1 1 d . . . H5 H 0.7655 0.4979 0.1811 0.027 Uiso 1 1 calc R . . C6 C 0.64855(15) 0.33083(18) 0.07464(19) 0.0281(5) Uani 1 1 d . . . H6A H 0.6508 0.2635 0.1169 0.042 Uiso 1 1 calc R . . H6B H 0.6968 0.3315 0.0575 0.042 Uiso 1 1 calc R . . H6C H 0.5986 0.3278 0.0112 0.042 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 0.01006(4) 0.00932(4) 0.01029(4) 0.000 0.00525(3) 0.000 Cl1 0.01184(18) 0.0282(2) 0.0237(2) -0.00059(19) 0.00536(17) 0.00195(18) Cl2 0.0264(3) 0.0107(3) 0.0237(3) 0.000 0.0114(3) 0.000 S1 0.0143(2) 0.0146(2) 0.0176(2) -0.00378(16) 0.00754(17) 0.00016(16) S2 0.0205(2) 0.0163(2) 0.0171(2) 0.00500(17) 0.00763(19) -0.00074(17) N1 0.0177(8) 0.0172(8) 0.0178(9) 0.0012(6) 0.0074(7) -0.0017(6) N2 0.0193(8) 0.0227(9) 0.0229(9) -0.0014(7) 0.0086(7) -0.0053(7) N3 0.0165(7) 0.0138(7) 0.0156(8) -0.0011(6) 0.0083(6) 0.0007(6) N4 0.0220(8) 0.0160(8) 0.0205(9) 0.0005(6) 0.0108(7) -0.0014(7) N5 0.0219(9) 0.0229(8) 0.0231(9) -0.0001(7) 0.0103(7) -0.0051(7) N6 0.0236(8) 0.0148(7) 0.0205(9) 0.0009(6) 0.0143(7) -0.0012(6) C1 0.0179(9) 0.0135(8) 0.0139(9) -0.0025(7) 0.0087(7) 0.0006(7) C2 0.0181(9) 0.0219(9) 0.0193(10) -0.0040(8) 0.0080(8) -0.0023(7) C3 0.0215(10) 0.0172(9) 0.0204(10) 0.0045(7) 0.0080(8) 0.0013(7) C4 0.0224(10) 0.0133(8) 0.0143(9) 0.0043(7) 0.0105(8) -0.0004(7) C5 0.0237(10) 0.0227(10) 0.0239(11) 0.0021(8) 0.0125(9) -0.0036(8) C6 0.0364(13) 0.0201(10) 0.0387(14) -0.0065(9) 0.0265(11) -0.0039(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 Bi1 Cl1 2.6584(5) 2_655 ? Bi1 Cl1 2.6584(5) . ? Bi1 S2 2.8004(5) . ? Bi1 S2 2.8004(5) 2_655 ? Bi1 S1 2.8582(5) 2_655 ? Bi1 S1 2.8582(5) . ? S1 C1 1.7130(19) . ? S2 C4 1.709(2) . ? N1 C1 1.331(2) . ? N1 N2 1.374(2) . ? N1 H1 0.86(3) . ? N2 C2 1.308(3) . ? N3 C1 1.360(2) . ? N3 C2 1.368(2) . ? N3 C3 1.465(2) . ? N4 C4 1.336(2) . ? N4 N5 1.374(2) . ? N4 H4 0.86(3) . ? N5 C5 1.304(3) . ? N6 C4 1.362(2) . ? N6 C5 1.371(3) . ? N6 C6 1.471(3) . ? C2 H2A 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 Cl1 Bi1 Cl1 178.03(2) 2_655 . ? Cl1 Bi1 S2 96.693(16) 2_655 . ? Cl1 Bi1 S2 81.901(16) . . ? Cl1 Bi1 S2 81.902(16) 2_655 2_655 ? Cl1 Bi1 S2 96.691(16) . 2_655 ? S2 Bi1 S2 89.76(2) . 2_655 ? Cl1 Bi1 S1 98.780(15) 2_655 2_655 ? Cl1 Bi1 S1 82.640(16) . 2_655 ? S2 Bi1 S1 164.522(14) . 2_655 ? S2 Bi1 S1 92.798(18) 2_655 2_655 ? Cl1 Bi1 S1 82.640(15) 2_655 . ? Cl1 Bi1 S1 98.780(15) . . ? S2 Bi1 S1 92.798(18) . . ? S2 Bi1 S1 164.523(14) 2_655 . ? S1 Bi1 S1 88.80(2) 2_655 . ? C1 S1 Bi1 97.04(6) . . ? C4 S2 Bi1 100.59(6) . . ? C1 N1 N2 112.90(16) . . ? C1 N1 H1 128.6(17) . . ? N2 N1 H1 118.5(17) . . ? C2 N2 N1 103.27(16) . . ? C1 N3 C2 107.01(16) . . ? C1 N3 C3 126.18(16) . . ? C2 N3 C3 126.78(16) . . ? C4 N4 N5 113.21(17) . . ? C4 N4 H4 126.8(18) . . ? N5 N4 H4 119.8(18) . . ? C5 N5 N4 102.98(16) . . ? C4 N6 C5 106.77(16) . . ? C4 N6 C6 126.24(17) . . ? C5 N6 C6 126.97(18) . . ? N1 C1 N3 104.95(16) . . ? N1 C1 S1 127.11(15) . . ? N3 C1 S1 127.94(14) . . ? N2 C2 N3 111.86(18) . . ? N2 C2 H2A 124.1 . . ? N3 C2 H2A 124.1 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 N6 104.64(17) . . ? N4 C4 S2 126.54(16) . . ? N6 C4 S2 128.79(15) . . ? N5 C5 N6 112.39(19) . . ? N5 C5 H5 123.8 . . ? N6 C5 H5 123.8 . . ? N6 C6 H6A 109.5 . . ? N6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.602 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.095 #===END _database_code_depnum_ccdc_archive 'CCDC 952332'