# 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_mow1rabs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Br4 N O Sb' _chemical_formula_weight 529.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.273(5) _cell_length_b 8.397(4) _cell_length_c 23.276(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2398.7(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5358 _cell_measurement_theta_min 2.9842 _cell_measurement_theta_max 28.6025 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.933 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 15.583 _exptl_absorpt_correction_type NUMERICAL _exptl_absorpt_correction_T_min 0.1466 _exptl_absorpt_correction_T_max 0.3048 _exptl_absorpt_process_details 'CRYSALIS V171.33.32' _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 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12066 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.66 _reflns_number_total 2959 _reflns_number_gt 2153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS V171.33.32' _computing_cell_refinement 'CRYSALIS V171.33.32' _computing_data_reduction 'CRYSALIS V171.33.32' _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^)+(0.0189P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2959 _refine_ls_number_parameters 100 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0426 _refine_ls_wR_factor_gt 0.0405 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _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 Sb1 Sb 0.66904(2) 0.46623(3) 0.371083(10) 0.01221(6) Uani 1 1 d . . . Br2 Br 0.67697(3) 0.22263(5) 0.298444(16) 0.01938(10) Uani 1 1 d . . . Br3 Br 0.65147(3) 0.76738(5) 0.440710(15) 0.01584(9) Uani 1 1 d . . . Br4 Br 0.53879(3) 0.33193(5) 0.441007(16) 0.01720(9) Uani 1 1 d . . . Br1 Br 0.51143(3) 0.57450(5) 0.309205(16) 0.01869(10) Uani 1 1 d . . . C5 C 0.1506(3) 0.4397(5) 0.44322(15) 0.0161(8) Uani 1 1 d . . . N4 N 0.0969(2) 0.3638(4) 0.39272(13) 0.0160(7) Uani 1 1 d D . . C2 C 0.1945(3) 0.5504(5) 0.33152(17) 0.0224(10) Uani 1 1 d . . . C6 C 0.2578(3) 0.5086(5) 0.42496(17) 0.0203(10) Uani 1 1 d . . . C4 C 0.0856(3) 0.4801(5) 0.34452(16) 0.0182(9) Uani 1 1 d . . . O1 O 0.2420(2) 0.6245(3) 0.38047(10) 0.0193(7) Uani 1 1 d . . . HN41 H 0.0314 0.3207 0.4016 0.035 Uiso 1 1 d D . . HN42 H 0.1425 0.2840 0.3812 0.048 Uiso 1 1 d D . . H2A H 0.1882 0.6211 0.3044 0.038 Uiso 1 1 d . . . H2B H 0.2443 0.4763 0.3201 0.023 Uiso 1 1 d . . . H3A H 0.0584 0.4263 0.3147 0.023 Uiso 1 1 d . . . H3B H 0.0305 0.5487 0.3556 0.020 Uiso 1 1 d . . . H5A H 0.1028 0.5100 0.4527 0.008 Uiso 1 1 d . . . H5B H 0.1618 0.3649 0.4761 0.017 Uiso 1 1 d . . . H6A H 0.3117 0.4240 0.4127 0.009 Uiso 1 1 d . . . H6B H 0.2883 0.5727 0.4560 0.025 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 Sb1 0.01130(12) 0.01368(13) 0.01167(12) -0.00029(11) -0.00015(10) 0.00069(11) Br2 0.0211(2) 0.0213(2) 0.01572(19) -0.00553(17) -0.00359(16) 0.00599(19) Br3 0.01310(18) 0.0205(2) 0.01387(18) -0.00207(16) 0.00076(15) -0.00028(17) Br4 0.01394(18) 0.0209(2) 0.01675(19) 0.00275(16) 0.00153(16) -0.00205(17) Br1 0.0183(2) 0.0225(2) 0.01518(19) -0.00223(17) -0.00434(16) 0.00746(18) C5 0.019(2) 0.018(2) 0.0111(18) 0.0005(16) 0.0009(16) 0.0006(18) N4 0.0110(16) 0.019(2) 0.0181(17) 0.0006(14) 0.0004(14) -0.0015(15) C2 0.026(2) 0.024(3) 0.018(2) 0.0021(18) 0.0026(18) -0.006(2) C6 0.021(2) 0.017(3) 0.024(2) -0.0009(17) -0.0006(18) -0.0016(19) C4 0.021(2) 0.018(2) 0.0157(19) 0.0015(17) -0.0051(17) 0.0006(19) O1 0.0245(15) 0.0178(17) 0.0156(14) -0.0012(11) -0.0008(12) -0.0053(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Br4 2.5448(7) . ? Sb1 Br1 2.5774(8) . ? Sb1 Br2 2.6556(10) . ? Sb1 Br3 3.0113(12) . ? Sb1 Br3 3.2042(9) 8_755 ? Sb1 Br2 3.3266(10) 8_765 ? C5 N4 1.490(5) . ? C5 C6 1.499(5) . ? N4 C4 1.494(5) . ? C2 O1 1.423(5) . ? C2 C4 1.492(5) . ? C6 O1 1.434(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br4 Sb1 Br1 92.42(3) . . ? Br4 Sb1 Br2 95.10(3) . . ? Br1 Sb1 Br2 86.76(3) . . ? Br4 Sb1 Br3 89.02(3) . . ? Br1 Sb1 Br3 87.18(2) . . ? Br2 Sb1 Br3 172.803(15) . . ? Br4 Sb1 Br3 82.96(3) . 8_755 ? Br1 Sb1 Br3 169.245(16) . 8_755 ? Br2 Sb1 Br3 84.00(3) . 8_755 ? Br3 Sb1 Br3 102.39(3) . 8_755 ? Br4 Sb1 Br2 165.639(16) . 8_765 ? Br1 Sb1 Br2 85.07(3) . 8_765 ? Br2 Sb1 Br2 98.87(3) . 8_765 ? Br3 Sb1 Br2 76.74(3) . 8_765 ? Br3 Sb1 Br2 101.76(3) 8_755 8_765 ? N4 C5 C6 109.2(3) . . ? C5 N4 C4 110.7(3) . . ? O1 C2 C4 112.2(3) . . ? O1 C6 C5 110.3(3) . . ? C2 C4 N4 109.1(3) . . ? C2 O1 C6 109.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 HN42 O1 0.91 1.95 2.833(4) 162.0 8_655 N4 HN41 Br3 0.91 2.46 3.346(3) 165.0 8_655 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.787 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.166 _database_code_depnum_ccdc_archive 'CCDC 939474' ####################################################################### # # 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_sbcl4_abs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Cl4 N O Sb' _chemical_formula_weight 351.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.776(4) _cell_length_b 8.293(3) _cell_length_c 22.415(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2189.0(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24518 _cell_measurement_theta_min 2.7250 _cell_measurement_theta_max 36.8750 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 3.449 _exptl_absorpt_correction_type NUMERICAL _exptl_absorpt_correction_T_min 0.355 _exptl_absorpt_correction_T_max 0.723 _exptl_absorpt_process_details 'CRYSALIS V171.33.32' _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 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3359 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38238 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 36.94 _reflns_number_total 5228 _reflns_number_gt 4507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS V171.33.32' _computing_cell_refinement 'CRYSALIS V171.33.32' _computing_data_reduction 'CRYSALIS V171.33.32' _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^)+(0.0210P)^2^+0.2312P] 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 5228 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0385 _refine_ls_wR_factor_gt 0.0372 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sb1 Sb 0.673960(5) 0.469337(8) 0.631077(3) 0.01116(2) Uani 1 1 d . . . Cl2 Cl 0.67091(2) 0.23744(3) 0.701602(11) 0.01961(5) Uani 1 1 d . . . Cl3 Cl 0.65571(2) 0.75300(3) 0.560295(10) 0.01566(4) Uani 1 1 d . . . Cl1 Cl 0.52406(2) 0.58468(3) 0.689996(11) 0.01898(5) Uani 1 1 d . . . Cl4 Cl 0.54223(2) 0.34443(3) 0.565145(11) 0.01783(5) Uani 1 1 d . . . O1 O 0.24837(7) 0.61683(10) 0.61689(3) 0.01840(15) Uani 1 1 d . . . N4 N 0.08803(7) 0.36307(11) 0.60527(4) 0.01373(15) Uani 1 1 d . . . C5 C 0.08523(10) 0.47536(13) 0.65758(5) 0.01781(19) Uani 1 1 d . . . C2 C 0.25499(9) 0.50588(14) 0.56787(5) 0.01699(18) Uani 1 1 d . . . C3 C 0.13830(9) 0.44479(14) 0.55191(5) 0.01604(18) Uani 1 1 d . . . C6 C 0.20391(12) 0.53772(15) 0.66887(5) 0.0222(2) Uani 1 1 d . . . HN41 H 0.0178(13) 0.3311(18) 0.5964(6) 0.022(4) Uiso 1 1 d . . . HN42 H 0.1318(15) 0.278(2) 0.6153(7) 0.028(4) Uiso 1 1 d . . . H2A H 0.3064(11) 0.4152(19) 0.5776(6) 0.013(3) Uiso 1 1 d . . . H2B H 0.2885(13) 0.5650(18) 0.5356(7) 0.019(4) Uiso 1 1 d . . . H3A H 0.1442(14) 0.368(2) 0.5211(7) 0.023(4) Uiso 1 1 d . . . H3B H 0.0886(14) 0.531(2) 0.5409(7) 0.029(4) Uiso 1 1 d . . . H5A H 0.0334(13) 0.5597(18) 0.6473(6) 0.015(3) Uiso 1 1 d . . . H5B H 0.0550(14) 0.419(2) 0.6904(7) 0.029(4) Uiso 1 1 d . . . H6A H 0.2547(15) 0.4499(18) 0.6801(7) 0.020(4) Uiso 1 1 d . . . H6B H 0.2020(14) 0.614(2) 0.6998(8) 0.033(4) 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 Sb1 0.01106(3) 0.01099(4) 0.01143(3) -0.00030(2) -0.00019(2) 0.00094(2) Cl2 0.02470(12) 0.01824(12) 0.01591(10) 0.00485(8) 0.00368(8) 0.00640(9) Cl3 0.01413(9) 0.01862(11) 0.01424(9) 0.00185(8) 0.00068(7) 0.00020(8) Cl1 0.02095(11) 0.02039(12) 0.01561(10) 0.00226(8) 0.00475(8) 0.00838(9) Cl4 0.01401(9) 0.02125(12) 0.01824(10) -0.00335(9) -0.00224(8) -0.00203(8) O1 0.0222(4) 0.0170(4) 0.0161(3) 0.0007(3) -0.0008(3) -0.0083(3) N4 0.0118(3) 0.0132(4) 0.0161(4) 0.0003(3) -0.0004(3) -0.0008(3) C5 0.0221(5) 0.0148(5) 0.0165(4) -0.0021(4) 0.0060(4) -0.0022(4) C2 0.0152(4) 0.0168(5) 0.0190(4) 0.0009(4) 0.0032(4) -0.0024(4) C3 0.0186(4) 0.0167(5) 0.0128(4) 0.0005(3) -0.0008(3) -0.0028(4) C6 0.0313(6) 0.0222(6) 0.0132(4) 0.0008(4) -0.0022(4) -0.0116(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 Sb1 Cl4 2.3798(5) . ? Sb1 Cl1 2.4031(6) . ? Sb1 Cl2 2.4897(7) . ? Sb1 Cl3 2.8456(8) . ? Sb1 Cl3 3.1240(7) 8_755 ? Sb1 Cl2 3.2832(7) 8_765 ? O1 C2 1.4354(14) . ? O1 C6 1.4360(14) . ? N4 C3 1.4967(14) . ? N4 C5 1.4978(14) . ? N4 HN41 0.891(15) . ? N4 HN42 0.904(18) . ? C5 C6 1.5115(17) . ? C5 H5A 0.956(15) . ? C5 H5B 0.940(16) . ? C2 C3 1.5076(16) . ? C2 H2A 0.989(15) . ? C2 H2B 0.959(16) . ? C3 H3A 0.944(16) . ? C3 H3B 0.957(17) . ? C6 H6A 0.976(16) . ? C6 H6B 0.940(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl4 Sb1 Cl1 92.05(2) . . ? Cl4 Sb1 Cl2 92.79(2) . . ? Cl1 Sb1 Cl2 87.016(19) . . ? Cl4 Sb1 Cl3 87.96(2) . . ? Cl1 Sb1 Cl3 85.519(18) . . ? Cl2 Sb1 Cl3 172.519(8) . . ? Cl4 Sb1 Cl3 81.56(2) . 8_755 ? Cl1 Sb1 Cl3 168.328(9) . 8_755 ? Cl2 Sb1 Cl3 83.58(2) . 8_755 ? Cl3 Sb1 Cl3 103.892(19) . 8_755 ? Cl4 Sb1 Cl2 163.029(9) . 8_765 ? Cl1 Sb1 Cl2 82.79(2) . 8_765 ? Cl2 Sb1 Cl2 103.03(2) . 8_765 ? Cl3 Sb1 Cl2 75.56(2) . 8_765 ? Cl3 Sb1 Cl2 106.03(2) 8_755 8_765 ? C2 O1 C6 110.37(9) . . ? C3 N4 C5 110.66(9) . . ? C3 N4 HN41 108.9(10) . . ? C5 N4 HN41 109.9(10) . . ? C3 N4 HN42 109.1(10) . . ? C5 N4 HN42 107.7(10) . . ? HN41 N4 HN42 110.6(14) . . ? N4 C5 C6 108.87(9) . . ? N4 C5 H5A 106.3(9) . . ? C6 C5 H5A 112.4(9) . . ? N4 C5 H5B 108.2(10) . . ? C6 C5 H5B 112.9(10) . . ? H5A C5 H5B 108.0(13) . . ? O1 C2 C3 110.33(9) . . ? O1 C2 H2A 110.6(9) . . ? C3 C2 H2A 110.7(8) . . ? O1 C2 H2B 105.8(9) . . ? C3 C2 H2B 111.6(9) . . ? H2A C2 H2B 107.6(12) . . ? N4 C3 C2 108.85(8) . . ? N4 C3 H3A 108.0(10) . . ? C2 C3 H3A 109.5(10) . . ? N4 C3 H3B 107.6(10) . . ? C2 C3 H3B 111.6(10) . . ? H3A C3 H3B 111.3(13) . . ? O1 C6 C5 110.95(9) . . ? O1 C6 H6A 109.1(9) . . ? C5 C6 H6A 110.8(10) . . ? O1 C6 H6B 107.4(11) . . ? C5 C6 H6B 109.4(10) . . ? H6A C6 H6B 109.1(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 HN41 Cl3 0.891(15) 2.291(15) 3.1761(13) 172.2(13) 8_655 N4 HN42 O1 0.904(18) 1.942(18) 2.8195(14) 163.0(15) 8_655 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.348 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 939475' ####################################################################### # # 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_p21c300 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Bi Br4 N O' _chemical_formula_weight 616.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.666(3) _cell_length_b 12.675(3) _cell_length_c 8.0870(16) _cell_angle_alpha 90.00 _cell_angle_beta 108.33(3) _cell_angle_gamma 90.00 _cell_volume 1232.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description UNSHAPED _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 27.232 _exptl_absorpt_correction_type NUMERICAL _exptl_absorpt_correction_T_min 0.5979 _exptl_absorpt_correction_T_max 1.4515 _exptl_absorpt_process_details 'CRYSALIS V172.33.42' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 KM4CCD _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 14637 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0753 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 29.63 _reflns_number_total 3297 _reflns_number_gt 2117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS V172.33.42' _computing_cell_refinement 'CRYSALIS V172.33.42' _computing_data_reduction 'CRYSALIS V172.33.42' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2' _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^)+(0.0150P)^2^+0.0150P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.001403(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3297 _refine_ls_number_parameters 141 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0426 _refine_ls_wR_factor_gt 0.0403 _refine_ls_goodness_of_fit_ref 0.819 _refine_ls_restrained_S_all 0.819 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.009 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 0.263184(5) 0.165624(5) 0.167939(8) 0.02312(2) Uani 1 1 d . . . Br4 Br 0.400415(16) 0.174439(16) 0.51501(2) 0.04627(7) Uani 1 1 d . . . Br3 Br 0.131125(15) 0.155575(14) -0.21167(2) 0.03396(6) Uani 1 1 d . . . Br2 Br 0.115206(16) 0.035182(15) 0.22818(3) 0.04460(6) Uani 1 1 d . . . Br1 Br 0.389026(16) 0.007095(16) 0.12185(3) 0.04884(7) Uani 1 1 d . . . O1 O 0.23014(10) 0.75859(10) 0.00722(14) 0.0416(4) Uani 1 1 d . . . C2 C 0.32714(15) 0.71820(19) 0.1324(2) 0.0541(7) Uani 1 1 d . . . C3 C 0.31084(17) 0.60604(18) 0.1720(2) 0.0595(8) Uani 1 1 d . . . N4 N 0.21428(13) 0.59652(11) 0.23636(18) 0.0391(5) Uani 1 1 d D . . C5 C 0.11434(15) 0.64415(15) 0.1114(2) 0.0409(6) Uani 1 1 d . . . C6 C 0.13810(16) 0.75441(14) 0.0738(2) 0.0364(6) Uani 1 1 d . . . HN41 H 0.2279(16) 0.6410(13) 0.3347(18) 0.084(7) Uiso 1 1 d D . . HN42 H 0.2047(14) 0.5416(11) 0.282(2) 0.076(7) Uiso 1 1 d D . . H2A H 0.3535(13) 0.7567(13) 0.2362(19) 0.049(5) Uiso 1 1 d . . . H2B H 0.3870(15) 0.7249(15) 0.083(2) 0.070(6) Uiso 1 1 d . . . H3A H 0.2891(14) 0.5834(13) 0.065(2) 0.056(6) Uiso 1 1 d . . . H3B H 0.3752(12) 0.5876(11) 0.2499(19) 0.035(5) Uiso 1 1 d . . . H5A H 0.0895(11) 0.6093(10) 0.0055(17) 0.019(4) Uiso 1 1 d . . . H5B H 0.0656(12) 0.6523(11) 0.1681(19) 0.029(4) Uiso 1 1 d . . . H6A H 0.0767(12) 0.7885(12) -0.0133(18) 0.038(5) Uiso 1 1 d . . . H6B H 0.1513(14) 0.7886(14) 0.173(2) 0.062(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 Bi1 0.02044(3) 0.02609(3) 0.02267(2) -0.00085(3) 0.00656(2) 0.00068(3) Br4 0.03338(10) 0.06391(13) 0.03244(9) -0.00899(10) -0.00265(8) 0.01761(10) Br3 0.02838(9) 0.03281(9) 0.03393(9) 0.00333(8) 0.00014(7) -0.00658(9) Br2 0.03931(10) 0.03845(10) 0.06099(11) 0.01074(9) 0.02285(8) -0.00492(9) Br1 0.03181(10) 0.05216(12) 0.05546(12) -0.01997(10) 0.00356(9) 0.01447(9) O1 0.0339(7) 0.0577(8) 0.0298(6) 0.0138(6) 0.0054(5) -0.0030(7) C2 0.0224(10) 0.0956(16) 0.0415(10) 0.0199(11) 0.0063(8) -0.0038(11) C3 0.0494(11) 0.0889(16) 0.0379(11) 0.0114(11) 0.0105(9) 0.0423(11) N4 0.0530(10) 0.0275(8) 0.0330(8) 0.0065(7) 0.0080(7) 0.0016(8) C5 0.0351(10) 0.0536(12) 0.0338(9) -0.0051(9) 0.0108(7) -0.0080(10) C6 0.0378(10) 0.0373(10) 0.0309(9) 0.0047(9) 0.0063(8) 0.0100(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 Br2 2.6567(4) . ? Bi1 Br1 2.6628(4) . ? Bi1 Br4 2.8006(10) . ? Bi1 Br3 3.0015(10) . ? Bi1 Br3 3.1474(5) 4_566 ? Bi1 Br4 3.1642(5) 4_565 ? Br4 Bi1 3.1642(5) 4_566 ? Br3 Bi1 3.1474(5) 4_565 ? O1 C2 1.419(2) . ? O1 C6 1.431(3) . ? C2 C3 1.486(3) . ? C2 H2A 0.937(15) . ? C2 H2B 0.96(2) . ? C3 N4 1.477(3) . ? C3 H3A 0.870(17) . ? C3 H3B 0.890(13) . ? N4 C5 1.478(2) . ? N4 HN41 0.945(15) . ? N4 HN42 0.816(15) . ? C5 C6 1.481(3) . ? C5 H5A 0.927(13) . ? C5 H5B 0.883(17) . ? C6 H6A 0.971(14) . ? C6 H6B 0.878(17) . ? 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 Br2 Bi1 Br1 92.518(17) . . ? Br2 Bi1 Br4 95.30(2) . . ? Br1 Bi1 Br4 87.720(18) . . ? Br2 Bi1 Br3 87.87(2) . . ? Br1 Bi1 Br3 89.449(18) . . ? Br4 Bi1 Br3 175.841(7) . . ? Br2 Bi1 Br3 85.250(18) . 4_566 ? Br1 Bi1 Br3 170.534(7) . 4_566 ? Br4 Bi1 Br3 83.337(16) . 4_566 ? Br3 Bi1 Br3 99.643(16) . 4_566 ? Br2 Bi1 Br4 167.502(8) . 4_565 ? Br1 Bi1 Br4 90.124(18) . 4_565 ? Br4 Bi1 Br4 97.011(16) . 4_565 ? Br3 Bi1 Br4 79.942(17) . 4_565 ? Br3 Bi1 Br4 94.030(18) 4_566 4_565 ? Bi1 Br4 Bi1 99.973(17) . 4_566 ? Bi1 Br3 Bi1 96.108(16) . 4_565 ? C2 O1 C6 110.06(14) . . ? O1 C2 C3 110.56(15) . . ? O1 C2 H2A 115.9(10) . . ? C3 C2 H2A 109.9(10) . . ? O1 C2 H2B 107.0(10) . . ? C3 C2 H2B 110.7(11) . . ? H2A C2 H2B 102.6(15) . . ? N4 C3 C2 109.92(18) . . ? N4 C3 H3A 106.6(12) . . ? C2 C3 H3A 97.1(11) . . ? N4 C3 H3B 113.9(11) . . ? C2 C3 H3B 104.2(10) . . ? H3A C3 H3B 123.4(15) . . ? C5 N4 C3 110.61(14) . . ? C5 N4 HN41 102.8(10) . . ? C3 N4 HN41 107.1(12) . . ? C5 N4 HN42 116.2(12) . . ? C3 N4 HN42 119.2(13) . . ? HN41 N4 HN42 98.1(15) . . ? N4 C5 C6 109.89(14) . . ? N4 C5 H5A 113.9(8) . . ? C6 C5 H5A 107.0(8) . . ? N4 C5 H5B 106.3(9) . . ? C6 C5 H5B 102.5(9) . . ? H5A C5 H5B 116.5(12) . . ? O1 C6 C5 110.77(15) . . ? O1 C6 H6A 105.8(10) . . ? C5 C6 H6A 113.6(9) . . ? O1 C6 H6B 112.3(12) . . ? C5 C6 H6B 105.7(12) . . ? H6A C6 H6B 108.7(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 Bi1 Br4 Bi1 -78.537(18) . . . 4_566 ? Br1 Bi1 Br4 Bi1 -170.856(7) . . . 4_566 ? Br3 Bi1 Br4 Bi1 142.00(8) . . . 4_566 ? Br3 Bi1 Br4 Bi1 6.037(6) 4_566 . . 4_566 ? Br4 Bi1 Br4 Bi1 99.300(19) 4_565 . . 4_566 ? Br2 Bi1 Br3 Bi1 171.610(6) . . . 4_565 ? Br1 Bi1 Br3 Bi1 -95.850(17) . . . 4_565 ? Br4 Bi1 Br3 Bi1 -48.75(8) . . . 4_565 ? Br3 Bi1 Br3 Bi1 86.795(18) 4_566 . . 4_565 ? Br4 Bi1 Br3 Bi1 -5.627(5) 4_565 . . 4_565 ? C6 O1 C2 C3 61.3(2) . . . . ? O1 C2 C3 N4 -58.1(2) . . . . ? C2 C3 N4 C5 54.50(18) . . . . ? C3 N4 C5 C6 -54.3(2) . . . . ? C2 O1 C6 C5 -61.26(18) . . . . ? N4 C5 C6 O1 57.50(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 HN41 O1 0.945(15) 1.882(16) 2.8168(19) 169.4(16) 4_576 N4 HN42 Br3 0.816(15) 2.673(15) 3.4313(16) 155.3(14) 4_566 _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 29.63 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 1.052 _refine_diff_density_min -0.974 _refine_diff_density_rms 0.182 _database_code_depnum_ccdc_archive 'CCDC 929943' ####################################################################### # # 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_346f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Bi Br4 N O' _chemical_formula_weight 616.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.744(3) _cell_length_b 14.106(3) _cell_length_c 7.5546(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.35(3) _cell_angle_gamma 90.00 _cell_volume 1303.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 346(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description UNSHAPED _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 25.755 _exptl_absorpt_correction_type NUMERICAL _exptl_absorpt_correction_T_min 0.6491 _exptl_absorpt_correction_T_max 1.5210 _exptl_absorpt_process_details 'CRYSALIS V171.33.42' _exptl_special_details ; ? ; _diffrn_ambient_temperature 346(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 KM4CCD _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 12094 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2972 _reflns_number_gt 1443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS V171.33.42' _computing_cell_refinement 'CRYSALIS V171.33.42' _computing_data_reduction 'CRYSALIS V171.33.42' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2' _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^)+(0.0200P)^2^+0.0400P] 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 2972 _refine_ls_number_parameters 100 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0695 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.921 _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 0.246456(12) 0.167461(9) 0.148432(18) 0.03859(4) Uani 1 1 d . . . Br1 Br 0.38285(4) 0.03298(3) 0.08266(6) 0.07919(18) Uani 1 1 d . . . Br2 Br 0.10971(4) 0.03750(3) 0.21836(6) 0.07296(17) Uani 1 1 d . . . Br3 Br 0.11484(3) 0.17101(3) -0.23630(5) 0.05325(13) Uani 1 1 d . . . Br4 Br 0.38054(3) 0.16857(3) 0.52577(5) 0.04952(13) Uani 1 1 d . . . O1 O 0.2545(3) -0.23897(17) 0.7148(4) 0.0887(12) Uani 1 1 d . . . C2 C 0.3548(4) -0.1890(3) 0.7205(6) 0.091(2) Uani 1 1 d D . . C3 C 0.3318(3) -0.1061(3) 0.5949(5) 0.0661(15) Uani 1 1 d D . . N4 N 0.2516(3) -0.04242(18) 0.6430(4) 0.0552(10) Uani 1 1 d D . . C5 C 0.1517(3) -0.0941(3) 0.6459(5) 0.0772(17) Uani 1 1 d D . . C6 C 0.1831(4) -0.1804(3) 0.7719(6) 0.0916(18) Uani 1 1 d D . . H3A H 0.3061 -0.1270 0.4717 0.050 Uiso 1 1 d D . . H3B H 0.3996 -0.0732 0.6078 0.050 Uiso 1 1 d D . . H2A H 0.4019 -0.2310 0.6794 0.050 Uiso 1 1 d D . . H2B H 0.3905 -0.1688 0.8397 0.050 Uiso 1 1 d D . . H4A H 0.2813 -0.0144 0.7526 0.050 Uiso 1 1 d D . . H4B H 0.2335 0.0051 0.5569 0.050 Uiso 1 1 d D . . H5A H 0.1162 -0.1165 0.5245 0.050 Uiso 1 1 d D . . H5B H 0.1040 -0.0545 0.6851 0.050 Uiso 1 1 d D . . H6A H 0.2154 -0.1571 0.8969 0.050 Uiso 1 1 d D . . H6B H 0.1191 -0.2138 0.7736 0.050 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.03805(7) 0.04688(7) 0.03379(6) -0.00159(8) 0.01492(5) -0.00012(9) Br1 0.0557(3) 0.0984(3) 0.0753(3) -0.0378(2) 0.0051(2) 0.0257(2) Br2 0.0548(3) 0.0925(3) 0.0646(3) 0.0195(2) 0.0053(2) -0.0294(2) Br3 0.0460(2) 0.0645(2) 0.0440(2) 0.0046(2) 0.00416(18) -0.0135(2) Br4 0.0408(2) 0.0604(2) 0.0436(2) -0.0056(2) 0.00577(17) 0.0060(2) O1 0.097(2) 0.0546(17) 0.110(2) 0.0081(16) 0.0226(18) 0.0070(17) C2 0.071(3) 0.097(4) 0.095(3) -0.001(3) 0.010(3) 0.024(3) C3 0.060(3) 0.095(3) 0.049(2) -0.001(2) 0.0246(19) 0.002(2) N4 0.0644(19) 0.0468(16) 0.0588(18) 0.0087(16) 0.0244(15) -0.0005(19) C5 0.067(3) 0.066(3) 0.109(3) 0.018(2) 0.044(2) 0.005(2) C6 0.069(3) 0.089(3) 0.121(3) 0.033(3) 0.034(3) -0.022(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 Br2 2.6823(6) . ? Bi1 Br1 2.7117(6) . ? Bi1 Br4 2.8816(10) . ? Bi1 Br3 2.9187(10) . ? Bi1 Br3 3.0961(6) 4_566 ? Bi1 Br4 3.1653(6) 4_565 ? Br3 Bi1 3.0961(6) 4_565 ? Br4 Bi1 3.1653(6) 4_566 ? O1 C6 1.384(6) . ? O1 C2 1.449(6) . ? C2 C3 1.483(6) . ? C2 H2A 0.9552 . ? C2 H2B 0.9325 . ? C3 N4 1.481(5) . ? C3 H3A 0.9428 . ? C3 H3B 0.9604 . ? N4 C5 1.473(5) . ? N4 H4A 0.8995 . ? N4 H4B 0.9172 . ? C5 C6 1.528(6) . ? C5 H5A 0.9544 . ? C5 H5B 0.9331 . ? C6 H6A 0.9750 . ? C6 H6B 0.9454 . ? 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 Br2 Bi1 Br1 92.49(2) . . ? Br2 Bi1 Br4 92.64(2) . . ? Br1 Bi1 Br4 87.30(2) . . ? Br2 Bi1 Br3 89.13(2) . . ? Br1 Bi1 Br3 92.74(2) . . ? Br4 Bi1 Br3 178.229(13) . . ? Br2 Bi1 Br3 90.81(2) . 4_566 ? Br1 Bi1 Br3 172.908(12) . 4_566 ? Br4 Bi1 Br3 86.278(18) . 4_566 ? Br3 Bi1 Br3 93.584(18) . 4_566 ? Br2 Bi1 Br4 172.403(12) . 4_565 ? Br1 Bi1 Br4 91.77(2) . 4_565 ? Br4 Bi1 Br4 93.841(18) . 4_565 ? Br3 Bi1 Br4 84.388(19) . 4_565 ? Br3 Bi1 Br4 85.67(2) 4_566 4_565 ? Bi1 Br3 Bi1 95.033(19) . 4_565 ? Bi1 Br4 Bi1 94.298(18) . 4_566 ? C6 O1 C2 110.6(3) . . ? O1 C2 C3 110.5(3) . . ? O1 C2 H2A 108.6 . . ? C3 C2 H2A 108.1 . . ? O1 C2 H2B 111.3 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.9 . . ? C2 C3 N4 110.3(4) . . ? C2 C3 H3A 109.6 . . ? N4 C3 H3A 111.1 . . ? C2 C3 H3B 107.8 . . ? N4 C3 H3B 110.2 . . ? H3A C3 H3B 107.7 . . ? C5 N4 C3 111.3(3) . . ? C5 N4 H4A 110.2 . . ? C3 N4 H4A 110.6 . . ? C5 N4 H4B 109.1 . . ? C3 N4 H4B 108.7 . . ? H4A N4 H4B 106.7 . . ? N4 C5 C6 109.1(3) . . ? N4 C5 H5A 109.1 . . ? C6 C5 H5A 107.8 . . ? N4 C5 H5B 110.6 . . ? C6 C5 H5B 111.1 . . ? H5A C5 H5B 109.2 . . ? O1 C6 C5 111.2(4) . . ? O1 C6 H6A 111.6 . . ? C5 C6 H6A 107.4 . . ? O1 C6 H6B 110.7 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 106.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 Bi1 Br3 Bi1 175.638(14) . . . 4_565 ? Br1 Bi1 Br3 Bi1 -91.91(2) . . . 4_565 ? Br4 Bi1 Br3 Bi1 -0.6(4) . . . 4_565 ? Br3 Bi1 Br3 Bi1 84.88(2) 4_566 . . 4_565 ? Br4 Bi1 Br3 Bi1 -0.402(12) 4_565 . . 4_565 ? Br2 Bi1 Br4 Bi1 -90.23(2) . . . 4_566 ? Br1 Bi1 Br4 Bi1 177.393(14) . . . 4_566 ? Br3 Bi1 Br4 Bi1 86.0(4) . . . 4_566 ? Br3 Bi1 Br4 Bi1 0.405(12) 4_566 . . 4_566 ? Br4 Bi1 Br4 Bi1 85.80(2) 4_565 . . 4_566 ? C6 O1 C2 C3 -61.1(5) . . . . ? O1 C2 C3 N4 56.5(4) . . . . ? C2 C3 N4 C5 -54.3(4) . . . . ? C3 N4 C5 C6 53.2(4) . . . . ? C2 O1 C6 C5 61.1(4) . . . . ? N4 C5 C6 O1 -57.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A Br1 0.90 2.55 3.440(3) 168.6 1_556 N4 H4B Br2 0.92 2.64 3.401(3) 140.9 . N4 H4B Br4 0.92 3.02 3.628(3) 125.2 . C6 H6A O1 0.98 2.74 3.406(5) 126.3 4_556 C3 H3A O1 0.94 2.66 3.521(5) 152.9 4 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.473 _refine_diff_density_min -0.919 _refine_diff_density_rms 0.205 _database_code_depnum_ccdc_archive 'CCDC 929944' ####################################################################### # # 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_210 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Bi Br4 N O' _chemical_formula_weight 616.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4513(11) _cell_length_b 12.6024(18) _cell_length_c 8.1075(16) _cell_angle_alpha 90.115(11) _cell_angle_beta 106.539(11) _cell_angle_gamma 96.441(13) _cell_volume 1211.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description UNSHAPED _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 27.712 _exptl_absorpt_correction_type NUMERICAL _exptl_absorpt_correction_T_min 0.6521 _exptl_absorpt_correction_T_max 1.3932 _exptl_absorpt_process_details 'CRYSALIS V171.33.42' _exptl_special_details ; ? ; _diffrn_ambient_temperature 210(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 KM4CCD _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 7467 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1499 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7467 _reflns_number_gt 4427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS V171.33.42' _computing_cell_refinement 'CRYSALIS V171.33.42' _computing_data_reduction 'CRYSALIS V171.33.42' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.2' _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^)+(0.0400P)^2^+0.0400P] 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 7467 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.023 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 0.763534(19) 0.695756(17) 0.65403(3) 0.01308(5) Uani 1 1 d . . . Bi2 Bi 0.760494(19) 0.864232(17) 0.15255(3) 0.01379(6) Uani 1 1 d . . . Br1 Br 0.62750(5) 0.67016(5) 0.29007(7) 0.01937(18) Uani 1 1 d . . . Br2 Br 0.89980(5) 0.71575(5) 0.00039(7) 0.02282(18) Uani 1 1 d . . . Br3 Br 0.89965(6) 0.86658(5) 0.48487(8) 0.0277(2) Uani 1 1 d . . . Br4 Br 0.63069(5) 0.85986(5) -0.22958(7) 0.02033(18) Uani 1 1 d . . . Br5 Br 0.61531(5) 0.54604(5) 0.72067(8) 0.02637(19) Uani 1 1 d . . . Br6 Br 0.89336(6) 0.55046(5) 0.59765(8) 0.0318(2) Uani 1 1 d . . . Br7 Br 0.88701(6) 1.03770(5) 0.10431(8) 0.0276(2) Uani 1 1 d . . . Br8 Br 0.60998(5) 0.97630(5) 0.22348(8) 0.02681(19) Uani 1 1 d . . . C2A C 0.8390(6) 0.2505(6) 0.6037(9) 0.044(2) Uani 1 1 d . . . C2B C 0.6414(6) 0.2555(4) 0.0633(7) 0.023(2) Uani 1 1 d . . . C3A C 0.8290(5) 0.1396(5) 0.6559(7) 0.027(2) Uani 1 1 d . . . C3B C 0.6078(5) 0.3584(5) 0.1074(7) 0.0186(17) Uani 1 1 d . . . C5A C 0.6258(5) 0.1568(5) 0.6068(8) 0.024(2) Uani 1 1 d . . . C5B C 0.8092(6) 0.4364(6) 0.1591(9) 0.042(3) Uani 1 1 d . . . C6A C 0.6494(6) 0.2690(6) 0.5644(8) 0.030(2) Uani 1 1 d . . . C6B C 0.8325(5) 0.3282(5) 0.1091(7) 0.0244(19) Uani 1 1 d . . . N4A N 0.7295(5) 0.1224(4) 0.7246(6) 0.0251(17) Uani 1 1 d . . . N4B N 0.7082(4) 0.4258(4) 0.2236(6) 0.0248(16) Uani 1 1 d . . . O1A O 0.7378(3) 0.2824(3) 0.4905(5) 0.0254(13) Uani 1 1 d . . . O1B O 0.7326(4) 0.2718(4) -0.0098(5) 0.0337(15) Uani 1 1 d . . . H4A1 H 0.7471 0.1529 0.8232 0.050 Uiso 1 1 d . . . H4A2 H 0.7174 0.0546 0.7393 0.050 Uiso 1 1 d . . . H4B1 H 0.7236 0.3991 0.3228 0.050 Uiso 1 1 d . . . H4B2 H 0.6892 0.4889 0.2375 0.050 Uiso 1 1 d . . . H2A1 H 0.8633 0.2956 0.7066 0.050 Uiso 1 1 d . . . H2A2 H 0.8985 0.2588 0.5490 0.050 Uiso 1 1 d . . . H2B1 H 0.6627 0.2143 0.1674 0.050 Uiso 1 1 d . . . H2B2 H 0.5770 0.2133 0.0172 0.050 Uiso 1 1 d . . . H3A1 H 0.8968 0.1265 0.7454 0.050 Uiso 1 1 d . . . H3A2 H 0.8202 0.0915 0.5613 0.050 Uiso 1 1 d . . . H3B1 H 0.5496 0.3450 0.1650 0.050 Uiso 1 1 d . . . H3B2 H 0.5766 0.3954 0.0043 0.050 Uiso 1 1 d . . . H5A1 H 0.5672 0.1493 0.6618 0.050 Uiso 1 1 d . . . H5A2 H 0.6043 0.1119 0.5057 0.050 Uiso 1 1 d . . . H5B1 H 0.8722 0.4702 0.2455 0.050 Uiso 1 1 d . . . H5B2 H 0.7949 0.4808 0.0598 0.050 Uiso 1 1 d . . . H6A1 H 0.5827 0.2901 0.4858 0.050 Uiso 1 1 d . . . H6A2 H 0.6678 0.3137 0.6671 0.050 Uiso 1 1 d . . . H6B1 H 0.8541 0.2869 0.2099 0.050 Uiso 1 1 d . . . H6B2 H 0.8918 0.3357 0.0565 0.050 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 Bi1 0.01180(9) 0.01366(9) 0.01492(8) -0.00071(9) 0.00536(7) 0.00221(9) Bi2 0.01228(10) 0.01446(9) 0.01539(9) 0.00069(9) 0.00498(7) 0.00211(9) Br1 0.0161(3) 0.0161(3) 0.0218(3) 0.0024(2) 0.0004(2) -0.0019(3) Br2 0.0157(3) 0.0314(3) 0.0204(3) -0.0047(3) 0.0014(2) 0.0094(3) Br3 0.0195(3) 0.0321(4) 0.0234(3) 0.0054(3) -0.0026(3) -0.0088(3) Br4 0.0144(3) 0.0200(3) 0.0244(3) -0.0023(3) 0.0002(2) 0.0072(3) Br5 0.0210(3) 0.0228(3) 0.0360(3) 0.0072(3) 0.0111(2) -0.0018(3) Br6 0.0208(3) 0.0354(3) 0.0372(3) -0.0151(3) 0.0003(3) 0.0157(3) Br7 0.0205(3) 0.0291(3) 0.0271(3) 0.0094(3) 0.0010(3) -0.0078(3) Br8 0.0247(3) 0.0218(3) 0.0391(3) -0.0051(3) 0.0158(2) 0.0071(3) C2A 0.017(4) 0.069(5) 0.038(4) -0.024(4) -0.012(3) 0.018(4) C2B 0.042(4) 0.013(3) 0.011(3) -0.005(2) 0.006(3) -0.008(3) C3A 0.028(3) 0.037(4) 0.022(3) 0.003(3) 0.017(2) 0.008(3) C3B 0.007(3) 0.035(3) 0.017(3) 0.007(3) 0.005(2) 0.012(3) C5A 0.015(3) 0.026(3) 0.033(3) 0.011(3) 0.011(2) 0.002(3) C5B 0.012(3) 0.050(5) 0.066(5) -0.003(4) 0.019(3) -0.014(3) C6A 0.018(3) 0.053(4) 0.014(3) -0.001(3) -0.007(3) 0.015(3) C6B 0.022(3) 0.040(4) 0.014(3) -0.005(3) 0.008(2) 0.011(3) N4A 0.044(3) 0.023(3) 0.006(2) -0.007(2) 0.000(2) 0.012(2) N4B 0.023(3) 0.036(3) 0.020(2) 0.006(2) 0.009(2) 0.015(2) O1A 0.021(2) 0.027(2) 0.033(2) 0.0211(18) 0.0120(18) 0.0103(18) O1B 0.020(2) 0.041(3) 0.039(2) -0.013(2) 0.007(2) 0.003(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 Br5 2.6549(8) . ? Bi1 Br6 2.6937(8) . ? Bi1 Br2 2.8313(8) 1_556 ? Bi1 Br1 2.9510(8) . ? Bi1 Br4 3.0905(8) 1_556 ? Bi1 Br3 3.1471(8) . ? Bi2 Br7 2.6448(8) . ? Bi2 Br8 2.6536(8) . ? Bi2 Br3 2.7554(8) . ? Bi2 Br4 3.0565(8) . ? Bi2 Br2 3.1574(8) . ? Bi2 Br1 3.1812(8) . ? Br2 Bi1 2.8313(8) 1_554 ? Br4 Bi1 3.0905(8) 1_554 ? C2A O1A 1.432(8) . ? C2A C3A 1.463(10) . ? C2A H2A1 0.9618 . ? C2A H2A2 0.9618 . ? C2B O1B 1.419(9) . ? C2B C3B 1.479(9) . ? C2B H2B1 0.9791 . ? C2B H2B2 0.8940 . ? C3A N4A 1.491(9) . ? C3A H3A1 0.9753 . ? C3A H3A2 0.9506 . ? C3B N4B 1.503(7) . ? C3B H3B1 0.9680 . ? C3B H3B2 0.9611 . ? C5A C6A 1.473(9) . ? C5A N4A 1.480(8) . ? C5A H5A1 0.9540 . ? C5A H5A2 0.9506 . ? C5B N4B 1.487(10) . ? C5B C6B 1.505(10) . ? C5B H5B1 0.9481 . ? C5B H5B2 0.9669 . ? C6A O1A 1.390(9) . ? C6A H6A1 0.9572 . ? C6A H6A2 0.9612 . ? C6B O1B 1.448(7) . ? C6B H6B1 0.9581 . ? C6B H6B2 0.9478 . ? N4A H4A1 0.8462 . ? N4A H4A2 0.8659 . ? N4B H4B1 0.8509 . ? N4B H4B2 0.8716 . ? 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 Br5 Bi1 Br6 92.41(2) . . ? Br5 Bi1 Br2 93.46(2) . 1_556 ? Br6 Bi1 Br2 88.20(2) . 1_556 ? Br5 Bi1 Br1 86.97(2) . . ? Br6 Bi1 Br1 89.72(2) . . ? Br2 Bi1 Br1 177.89(2) 1_556 . ? Br5 Bi1 Br4 86.57(2) . 1_556 ? Br6 Bi1 Br4 172.337(19) . 1_556 ? Br2 Bi1 Br4 84.28(2) 1_556 1_556 ? Br1 Bi1 Br4 97.80(2) . 1_556 ? Br5 Bi1 Br3 166.224(18) . . ? Br6 Bi1 Br3 88.44(2) . . ? Br2 Bi1 Br3 100.31(2) 1_556 . ? Br1 Bi1 Br3 79.28(2) . . ? Br4 Bi1 Br3 94.36(2) 1_556 . ? Br7 Bi2 Br8 92.84(2) . . ? Br7 Bi2 Br3 87.77(2) . . ? Br8 Bi2 Br3 96.11(2) . . ? Br7 Bi2 Br4 88.77(2) . . ? Br8 Bi2 Br4 89.76(2) . . ? Br3 Bi2 Br4 173.33(2) . . ? Br7 Bi2 Br2 91.51(2) . . ? Br8 Bi2 Br2 168.402(18) . . ? Br3 Bi2 Br2 94.80(2) . . ? Br4 Bi2 Br2 79.59(2) . . ? Br7 Bi2 Br1 168.474(19) . . ? Br8 Bi2 Br1 83.85(2) . . ? Br3 Bi2 Br1 81.63(2) . . ? Br4 Bi2 Br1 102.23(2) . . ? Br2 Bi2 Br1 93.86(2) . . ? Bi1 Br1 Bi2 96.66(2) . . ? Bi1 Br2 Bi2 99.43(2) 1_554 . ? Bi2 Br3 Bi1 101.67(2) . . ? Bi2 Br4 Bi1 96.14(2) . 1_554 ? O1A C2A C3A 114.5(5) . . ? O1A C2A H2A1 110.1 . . ? C3A C2A H2A1 107.7 . . ? O1A C2A H2A2 109.9 . . ? C3A C2A H2A2 107.1 . . ? H2A1 C2A H2A2 107.3 . . ? O1B C2B C3B 111.3(5) . . ? O1B C2B H2B1 109.9 . . ? C3B C2B H2B1 109.1 . . ? O1B C2B H2B2 125.0 . . ? C3B C2B H2B2 105.7 . . ? H2B1 C2B H2B2 94.0 . . ? C2A C3A N4A 107.8(6) . . ? C2A C3A H3A1 110.0 . . ? N4A C3A H3A1 109.6 . . ? C2A C3A H3A2 110.8 . . ? N4A C3A H3A2 110.6 . . ? H3A1 C3A H3A2 107.9 . . ? C2B C3B N4B 109.8(5) . . ? C2B C3B H3B1 109.5 . . ? N4B C3B H3B1 109.6 . . ? C2B C3B H3B2 110.1 . . ? N4B C3B H3B2 110.4 . . ? H3B1 C3B H3B2 107.4 . . ? C6A C5A N4A 109.0(5) . . ? C6A C5A H5A1 110.5 . . ? N4A C5A H5A1 109.1 . . ? C6A C5A H5A2 110.6 . . ? N4A C5A H5A2 108.2 . . ? H5A1 C5A H5A2 109.4 . . ? N4B C5B C6B 110.1(5) . . ? N4B C5B H5B1 109.5 . . ? C6B C5B H5B1 110.3 . . ? N4B C5B H5B2 108.6 . . ? C6B C5B H5B2 109.7 . . ? H5B1 C5B H5B2 108.5 . . ? O1A C6A C5A 111.4(6) . . ? O1A C6A H6A1 109.6 . . ? C5A C6A H6A1 108.5 . . ? O1A C6A H6A2 109.6 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 108.2 . . ? O1B C6B C5B 110.5(5) . . ? O1B C6B H6B1 108.5 . . ? C5B C6B H6B1 109.4 . . ? O1B C6B H6B2 109.2 . . ? C5B C6B H6B2 109.9 . . ? H6B1 C6B H6B2 109.3 . . ? C5A N4A C3A 113.2(5) . . ? C5A N4A H4A1 112.6 . . ? C3A N4A H4A1 108.3 . . ? C5A N4A H4A2 108.5 . . ? C3A N4A H4A2 107.3 . . ? H4A1 N4A H4A2 106.7 . . ? C5B N4B C3B 113.9(5) . . ? C5B N4B H4B1 110.3 . . ? C3B N4B H4B1 108.4 . . ? C5B N4B H4B2 109.5 . . ? C3B N4B H4B2 108.7 . . ? H4B1 N4B H4B2 105.7 . . ? C6A O1A C2A 111.2(5) . . ? C2B O1B C6B 111.9(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br5 Bi1 Br1 Bi2 173.03(2) . . . . ? Br6 Bi1 Br1 Bi2 -94.54(2) . . . . ? Br2 Bi1 Br1 Bi2 -85.2(5) 1_556 . . . ? Br4 Bi1 Br1 Bi2 86.91(2) 1_556 . . . ? Br3 Bi1 Br1 Bi2 -6.076(18) . . . . ? Br7 Bi2 Br1 Bi1 -16.43(12) . . . . ? Br8 Bi2 Br1 Bi1 -90.23(2) . . . . ? Br3 Bi2 Br1 Bi1 6.90(2) . . . . ? Br4 Bi2 Br1 Bi1 -178.643(19) . . . . ? Br2 Bi2 Br1 Bi1 101.18(2) . . . . ? Br7 Bi2 Br2 Bi1 -94.27(2) . . . 1_554 ? Br8 Bi2 Br2 Bi1 17.75(11) . . . 1_554 ? Br3 Bi2 Br2 Bi1 177.84(2) . . . 1_554 ? Br4 Bi2 Br2 Bi1 -5.805(18) . . . 1_554 ? Br1 Bi2 Br2 Bi1 95.93(2) . . . 1_554 ? Br7 Bi2 Br3 Bi1 168.90(2) . . . . ? Br8 Bi2 Br3 Bi1 76.28(2) . . . . ? Br4 Bi2 Br3 Bi1 -132.28(16) . . . . ? Br2 Bi2 Br3 Bi1 -99.77(2) . . . . ? Br1 Bi2 Br3 Bi1 -6.56(2) . . . . ? Br5 Bi1 Br3 Bi2 3.37(10) . . . . ? Br6 Bi1 Br3 Bi2 97.13(3) . . . . ? Br2 Bi1 Br3 Bi2 -174.98(2) 1_556 . . . ? Br1 Bi1 Br3 Bi2 7.12(2) . . . . ? Br4 Bi1 Br3 Bi2 -90.01(2) 1_556 . . . ? Br7 Bi2 Br4 Bi1 97.04(2) . . . 1_554 ? Br8 Bi2 Br4 Bi1 -170.116(19) . . . 1_554 ? Br3 Bi2 Br4 Bi1 38.27(17) . . . 1_554 ? Br2 Bi2 Br4 Bi1 5.275(16) . . . 1_554 ? Br1 Bi2 Br4 Bi1 -86.46(2) . . . 1_554 ? O1A C2A C3A N4A -52.2(7) . . . . ? O1B C2B C3B N4B -55.1(6) . . . . ? N4A C5A C6A O1A 57.7(6) . . . . ? N4B C5B C6B O1B 53.1(7) . . . . ? C6A C5A N4A C3A -54.5(7) . . . . ? C2A C3A N4A C5A 51.2(6) . . . . ? C6B C5B N4B C3B -49.6(7) . . . . ? C2B C3B N4B C5B 50.4(7) . . . . ? C5A C6A O1A C2A -59.3(6) . . . . ? C3A C2A O1A C6A 58.0(7) . . . . ? C3B C2B O1B C6B 61.9(6) . . . . ? C5B C6B O1B C2B -60.4(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4A H4A1 O1B 0.85 2.07 2.847(7) 151.6 1_556 N4A H4A2 Br4 0.87 2.61 3.457(5) 166.1 1_546 N4B H4B1 O1A 0.85 1.99 2.791(6) 155.9 . N4B H4B2 Br1 0.87 2.56 3.433(5) 176.8 . C2B H2B1 O1A 0.98 2.62 3.330(6) 129.1 . C6A H6A2 O1B 0.96 2.59 3.309(7) 132.1 1_556 C5B H5B1 Br6 0.95 2.96 3.651(7) 131.1 . N4B H4B1 Br6 0.85 3.08 3.489(4) 112.2 . N4A H4A1 Br7 0.85 2.94 3.393(4) 115.4 1_546 N4A H4A2 Br4 0.87 2.61 3.457(5) 166.1 1_546 C3A H3A2 Br3 0.95 3.22 3.987(7) 139.0 1_545 C5A H5A2 Br8 0.95 2.87 3.794(6) 163.0 1_545 C3B H3B2 Br5 0.96 3.09 3.947(6) 148.8 1_554 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 2.761 _refine_diff_density_min -2.606 _refine_diff_density_rms 0.463 _database_code_depnum_ccdc_archive 'CCDC 929945'