# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1526 data_pb108b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H8 Br2 N2 Se' _chemical_formula_weight 310.89 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' 'Se' 'Se' -0.1280 2.1120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2990 2.3550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c' 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 6.0102(4) _cell_length_b 15.6972(11) _cell_length_c 8.7387(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.250(2) _cell_angle_gamma 90.00 _cell_volume 805.67(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 14.492 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68750 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4024 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.36 _reflns_number_total 1786 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0522P)^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 1786 _refine_ls_number_parameters 81 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.31666(6) 0.31939(3) 0.07967(4) 0.01467(14) Uani 1 d . . . Br1 Br 0.58564(6) 0.20521(3) -0.03973(4) 0.01818(14) Uani 1 d . . . Br2 Br 0.04563(7) 0.41401(3) 0.16638(5) 0.02324(15) Uani 1 d . . . N1 N -0.0183(6) 0.3049(3) -0.1926(5) 0.0210(8) Uani 1 d . . . H1B H -0.090(12) 0.274(5) -0.131(9) 0.08(3) Uiso 1 d . . . H1A H -0.070(9) 0.312(3) -0.277(7) 0.026(15) Uiso 1 d . . . N3 N 0.2695(5) 0.3945(2) -0.2241(4) 0.0159(7) Uani 1 d . . . C2 C 0.1766(6) 0.3427(2) -0.1379(4) 0.0145(7) Uani 1 d . . . C4 C 0.1490(7) 0.4149(3) -0.3845(5) 0.0218(9) Uani 1 d . . . H4A H 0.0019 0.3855 -0.4075 0.033 Uiso 1 calc R . . H4B H 0.2407 0.3964 -0.4587 0.033 Uiso 1 calc R . . H4C H 0.1240 0.4766 -0.3943 0.033 Uiso 1 calc R . . C5 C 0.4920(7) 0.4353(3) -0.1759(5) 0.0213(9) Uani 1 d . . . H5A H 0.5602 0.4189 -0.0679 0.032 Uiso 1 calc R . . H5B H 0.4736 0.4973 -0.1821 0.032 Uiso 1 calc R . . H5C H 0.5913 0.4170 -0.2452 0.032 Uiso 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 Se1 0.0173(2) 0.0180(3) 0.0088(2) 0.00099(14) 0.00294(15) -0.00104(14) Br1 0.0163(2) 0.0257(3) 0.0126(2) 0.00188(15) 0.00309(15) 0.00048(15) Br2 0.0279(3) 0.0248(3) 0.0177(2) -0.00335(16) 0.00638(17) 0.00508(16) N1 0.0202(18) 0.033(2) 0.0099(17) 0.0013(15) 0.0024(14) -0.0020(15) N3 0.0171(16) 0.0181(18) 0.0126(16) 0.0018(13) 0.0037(12) -0.0007(13) C2 0.0173(18) 0.015(2) 0.0123(17) 0.0028(16) 0.0062(13) 0.0023(15) C4 0.028(2) 0.025(2) 0.0112(19) 0.0047(17) 0.0024(16) 0.0021(17) C5 0.022(2) 0.025(2) 0.018(2) 0.0007(17) 0.0055(16) -0.0058(17) _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 Se1 C2 1.943(4) . ? Se1 Br2 2.4408(6) . ? Se1 Br1 2.7623(6) . ? N1 C2 1.309(5) . ? N3 C2 1.312(5) . ? N3 C5 1.461(5) . ? N3 C4 1.470(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 C2 Se1 Br2 90.57(11) . . ? C2 Se1 Br1 85.38(11) . . ? Br2 Se1 Br1 174.11(2) . . ? C2 N3 C5 125.5(3) . . ? C2 N3 C4 119.9(3) . . ? C5 N3 C4 114.6(3) . . ? N1 C2 N3 121.9(4) . . ? N1 C2 Se1 116.1(3) . . ? N3 C2 Se1 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.856 _diffrn_reflns_theta_full 27.36 _diffrn_measured_fraction_theta_full 0.856 _refine_diff_density_max 1.392 _refine_diff_density_min -0.985 _refine_diff_density_rms 0.269 data_pinib _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H10 Br2 Cl2 N2 Se' _chemical_formula_weight 395.82 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' 'Br' 'Br' -0.2901 2.4595 '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' 'Se' 'Se' -0.0929 2.2259 '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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 5.9721(10) _cell_length_b 22.241(2) _cell_length_c 8.9466(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.503(10) _cell_angle_gamma 90.00 _cell_volume 1150.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 10.624 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1428 _exptl_absorpt_correction_T_max 0.6187 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2212 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2011 _reflns_number_gt 1393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0600P)^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 2011 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.50050(13) 0.79972(4) 0.55401(9) 0.0202(2) Uani 1 d . . . Br1 Br 0.75729(13) 0.71793(4) 0.43595(9) 0.0229(2) Uani 1 d . . . Br2 Br 0.24649(17) 0.87342(5) 0.62750(11) 0.0406(3) Uani 1 d . . . Cl1 Cl 0.7144(5) 0.53314(13) 0.4390(3) 0.0488(7) Uani 1 d . . . Cl2 Cl 0.8219(5) 0.49647(14) 0.1537(3) 0.0547(8) Uani 1 d . . . N1 N 0.1603(13) 0.7872(4) 0.2813(8) 0.028(2) Uani 1 d . . . N3 N 0.4408(10) 0.8528(3) 0.2565(7) 0.0174(15) Uani 1 d . . . C2 C 0.3541(12) 0.8157(4) 0.3381(9) 0.0163(18) Uani 1 d . . . C4 C 0.3141(18) 0.8659(6) 0.0959(11) 0.027(2) Uani 1 d . . . C5 C 0.6613(16) 0.8842(5) 0.3116(12) 0.034(2) Uani 1 d . . . C6 C 0.834(2) 0.5549(5) 0.2856(12) 0.042(3) Uani 1 d . . . H1A H 0.114(17) 0.774(5) 0.322(12) 0.025 Uiso 1 d . . . H1B H 0.057(14) 0.795(4) 0.182(10) 0.02(2) Uiso 1 d . . . H4A H 0.385(12) 0.898(4) 0.069(8) 0.01(2) Uiso 1 d . . . H4B H 0.274(16) 0.838(4) 0.057(11) 0.02(3) Uiso 1 d . . . H4C H 0.19(2) 0.890(6) 0.096(15) 0.10(5) Uiso 1 d . . . H5A H 0.633(12) 0.925(4) 0.321(8) 0.01(2) Uiso 1 d . . . H5B H 0.776(19) 0.884(5) 0.231(13) 0.06(3) Uiso 1 d . . . H5C H 0.753(16) 0.867(4) 0.414(12) 0.05(3) Uiso 1 d . . . H6A H 1.025(17) 0.552(4) 0.343(12) 0.05(3) Uiso 1 d . . . H6B H 0.716(19) 0.590(5) 0.269(12) 0.06(3) Uiso 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 Se1 0.0198(4) 0.0313(5) 0.0093(4) 0.0020(4) 0.0034(3) 0.0009(4) Br1 0.0192(4) 0.0354(6) 0.0135(4) 0.0008(4) 0.0032(3) 0.0027(4) Br2 0.0400(6) 0.0580(8) 0.0237(5) -0.0080(5) 0.0076(4) 0.0187(5) Cl1 0.0640(17) 0.0486(18) 0.0465(16) 0.0049(13) 0.0377(14) 0.0086(14) Cl2 0.0695(19) 0.064(2) 0.0357(14) -0.0083(14) 0.0239(13) -0.0050(16) N1 0.027(4) 0.040(6) 0.015(4) 0.010(4) 0.003(3) -0.014(4) N3 0.015(3) 0.027(4) 0.012(3) 0.001(3) 0.005(3) -0.006(3) C2 0.013(4) 0.023(5) 0.015(4) -0.003(3) 0.006(3) 0.002(3) C4 0.033(6) 0.030(7) 0.013(5) 0.011(5) -0.005(4) -0.004(5) C5 0.026(5) 0.042(8) 0.033(6) 0.012(5) 0.007(4) -0.003(5) C6 0.053(7) 0.044(7) 0.038(6) 0.007(5) 0.027(5) 0.008(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 Se1 C2 1.943(8) . ? Se1 Br2 2.4332(13) . ? Se1 Br1 2.7546(12) . ? Cl1 C6 1.767(10) . ? Cl2 C6 1.745(11) . ? N1 C2 1.306(11) . ? N3 C2 1.292(10) . ? N3 C5 1.463(11) . ? N3 C4 1.476(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Se1 Br2 89.4(2) . . ? C2 Se1 Br1 84.0(2) . . ? Br2 Se1 Br1 173.30(4) . . ? C2 N3 C5 124.6(7) . . ? C2 N3 C4 119.7(7) . . ? C5 N3 C4 115.7(7) . . ? N3 C2 N1 122.1(7) . . ? N3 C2 Se1 122.3(6) . . ? N1 C2 Se1 115.6(6) . . ? Cl2 C6 Cl1 111.4(6) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.073 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.175 data_rob _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16.50 H15 Br4 Cl N2 S2 Se2' _chemical_formula_weight 818.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 12.265(3) _cell_length_b 13.625(3) _cell_length_c 14.222(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.73(3) _cell_angle_gamma 90.00 _cell_volume 2376.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 10.134 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1256 _exptl_absorpt_correction_T_max 0.2364 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4381 _diffrn_reflns_av_R_equivalents 0.1110 _diffrn_reflns_av_sigmaI/netI 0.2231 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 24.98 _reflns_number_total 4181 _reflns_number_gt 1589 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 w=1/[\s^2^(Fo^2^)+(0.0045P)^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 4181 _refine_ls_number_parameters 263 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2352 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.006 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.80864(16) 0.91042(13) 0.21432(14) 0.0302(5) Uani 1 d . . . Br1 Br 0.92860(15) 0.90597(15) 0.06864(13) 0.0423(6) Uani 1 d . . . Br2 Br 0.68997(14) 0.89402(13) 0.35951(13) 0.0402(5) Uani 1 d . . . S3 S 0.7188(4) 0.7173(3) 0.1226(3) 0.0404(13) Uani 1 d . . . N1 N 0.8525(10) 0.7086(9) 0.2562(9) 0.027(3) Uani 1 d . . . C2 C 0.8009(12) 0.7699(10) 0.2050(11) 0.024(4) Uani 1 d . . . C4 C 0.7615(12) 0.5993(11) 0.1627(10) 0.024(4) Uani 1 d . . . C5 C 0.7279(13) 0.5145(12) 0.1243(11) 0.038(5) Uani 1 d . . . H5 H 0.6793 0.5112 0.0728 0.045 Uiso 1 calc R . . C6 C 0.7707(14) 0.4339(13) 0.1668(12) 0.043(5) Uani 1 d . . . H6 H 0.7480 0.3720 0.1449 0.051 Uiso 1 calc R . . C7 C 0.8447(14) 0.4367(12) 0.2395(13) 0.037(5) Uani 1 d . . . H7 H 0.8744 0.3785 0.2645 0.044 Uiso 1 calc R . . C8 C 0.8751(12) 0.5281(14) 0.2756(11) 0.040(5) Uani 1 d . . . H8 H 0.9254 0.5333 0.3258 0.048 Uiso 1 calc R . . C9 C 0.8285(12) 0.6114(13) 0.2349(12) 0.029(5) Uani 1 d . . . C10 C 0.9218(12) 0.7340(11) 0.3350(10) 0.035(4) Uani 1 d . . . H10A H 0.9499 0.6745 0.3639 0.053 Uiso 1 calc R . . H10B H 0.8801 0.7706 0.3806 0.053 Uiso 1 calc R . . H10C H 0.9821 0.7738 0.3134 0.053 Uiso 1 calc R . . Se1A Se 0.66520(15) 1.14624(14) 0.37877(14) 0.0325(5) Uani 1 d . . . Br1A Br 0.52695(14) 1.14647(14) 0.50584(13) 0.0437(6) Uani 1 d . . . Br2A Br 0.80557(16) 1.16141(14) 0.24383(14) 0.0499(6) Uani 1 d . . . S3A S 0.5375(3) 1.3248(3) 0.2960(3) 0.0380(12) Uani 1 d . . . N1A N 0.6831(11) 1.3515(10) 0.4206(10) 0.042(4) Uani 1 d . . . C2A C 0.6382(12) 1.2810(11) 0.3692(11) 0.027(4) Uani 1 d . . . C4A C 0.5546(12) 1.4428(10) 0.3370(11) 0.028(4) Uani 1 d . . . C5A C 0.4960(14) 1.5255(13) 0.3163(13) 0.057(6) Uani 1 d . . . H5A H 0.4386 1.5239 0.2719 0.069 Uiso 1 calc R . . C6A C 0.5234(13) 1.6120(12) 0.3623(12) 0.046(5) Uani 1 d . . . H6A H 0.4856 1.6704 0.3485 0.056 Uiso 1 calc R . . C7A C 0.6073(15) 1.6116(12) 0.4291(12) 0.054(6) Uani 1 d . . . H7A H 0.6260 1.6708 0.4590 0.064 Uiso 1 calc R . . C8A C 0.6626(13) 1.5301(13) 0.4526(12) 0.044(5) Uani 1 d . . . H8A H 0.7175 1.5314 0.4992 0.053 Uiso 1 calc R . . C9A C 0.6357(13) 1.4430(12) 0.4052(11) 0.028(4) Uani 1 d . . . C10A C 0.7682(11) 1.3367(12) 0.4872(11) 0.051(5) Uani 1 d . . . H10D H 0.7861 1.3986 0.5173 0.077 Uiso 1 calc R . . H10E H 0.8320 1.3114 0.4557 0.077 Uiso 1 calc R . . H10F H 0.7448 1.2900 0.5343 0.077 Uiso 1 calc R . . Cl1 Cl 1.0059(9) 0.6392(9) 0.0326(8) 0.066(4) Uani 0.50 d PD . . Cl2 Cl 0.9801(17) 0.4402(13) -0.0303(16) 0.113(8) Uani 0.50 d PD . . C11 C 1.044(5) 0.5160(16) 0.054(3) 0.043(16) Uani 0.50 d PD . . H11A H 1.0215 0.4965 0.1171 0.051 Uiso 0.50 calc PR . . H11B H 1.1231 0.5092 0.0500 0.051 Uiso 0.50 calc PR . . 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 Se1 0.0315(11) 0.0247(11) 0.0343(11) 0.0013(10) 0.0020(8) -0.0007(10) Br1 0.0326(11) 0.0547(15) 0.0396(12) -0.0010(12) 0.0049(9) -0.0099(11) Br2 0.0413(12) 0.0349(11) 0.0446(13) 0.0020(10) 0.0120(9) 0.0023(10) S3 0.045(3) 0.028(3) 0.048(3) 0.001(2) -0.011(3) -0.003(2) N1 0.034(9) 0.022(8) 0.026(9) -0.005(7) -0.014(7) -0.006(7) C2 0.021(9) 0.016(9) 0.034(11) 0.013(8) 0.013(8) 0.009(8) C4 0.034(10) 0.013(9) 0.026(10) 0.004(8) 0.013(8) 0.010(9) C5 0.052(13) 0.044(12) 0.017(10) -0.014(10) -0.004(9) 0.000(10) C6 0.051(13) 0.037(12) 0.040(13) 0.021(10) 0.016(10) -0.014(10) C7 0.043(13) 0.017(10) 0.050(13) 0.016(9) 0.009(10) 0.017(9) C8 0.016(10) 0.078(15) 0.026(11) -0.027(11) 0.002(8) 0.004(11) C9 0.014(10) 0.033(11) 0.041(12) 0.018(10) 0.012(9) 0.004(9) C10 0.034(10) 0.036(11) 0.035(11) 0.018(9) -0.009(8) 0.010(8) Se1A 0.0323(11) 0.0232(11) 0.0421(12) 0.0008(10) 0.0024(9) -0.0001(9) Br1A 0.0354(12) 0.0359(13) 0.0602(14) 0.0101(11) 0.0141(10) 0.0085(10) Br2A 0.0608(14) 0.0353(12) 0.0543(15) 0.0027(11) 0.0238(12) 0.0046(12) S3A 0.038(3) 0.027(3) 0.049(3) -0.008(2) -0.018(2) -0.001(2) N1A 0.042(10) 0.027(9) 0.058(11) 0.008(9) 0.008(8) 0.008(8) C2A 0.026(10) 0.024(10) 0.033(11) -0.021(9) 0.014(8) -0.003(8) C4A 0.035(11) 0.010(9) 0.039(11) 0.014(8) -0.009(9) 0.011(8) C5A 0.056(14) 0.040(12) 0.075(16) -0.013(12) -0.023(11) 0.010(11) C6A 0.049(12) 0.025(11) 0.065(14) -0.001(10) -0.007(10) 0.008(10) C7A 0.081(16) 0.036(12) 0.043(12) -0.001(11) -0.027(11) -0.007(13) C8A 0.045(13) 0.037(12) 0.049(13) 0.006(10) -0.026(10) 0.007(11) C9A 0.041(12) 0.030(11) 0.014(10) -0.008(8) -0.002(8) 0.004(9) C10A 0.030(10) 0.047(12) 0.074(14) -0.003(11) -0.035(10) 0.008(10) Cl1 0.048(7) 0.082(9) 0.066(8) 0.020(8) -0.007(6) 0.007(8) Cl2 0.094(14) 0.107(16) 0.140(19) -0.037(16) 0.063(12) -0.029(14) C11 0.09(4) 0.03(3) 0.01(2) -0.02(2) 0.01(2) 0.01(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 Se1 C2 1.921(14) . ? Se1 Br2 2.551(3) . ? Se1 Br1 2.557(3) . ? S3 C2 1.694(16) . ? S3 C4 1.783(14) . ? N1 C2 1.271(16) . ? N1 C9 1.390(18) . ? N1 C10 1.440(17) . ? C4 C9 1.317(19) . ? C4 C5 1.341(19) . ? C5 C6 1.36(2) . ? C6 C7 1.37(2) . ? C7 C8 1.40(2) . ? C8 C9 1.39(2) . ? Se1A C2A 1.870(15) . ? Se1A Br1A 2.494(3) . ? Se1A Br2A 2.602(3) . ? S3A C2A 1.712(16) . ? S3A C4A 1.722(15) . ? N1A C2A 1.324(17) . ? N1A C9A 1.392(18) . ? N1A C10A 1.415(16) . ? C4A C9A 1.381(19) . ? C4A C5A 1.366(19) . ? C5A C6A 1.39(2) . ? C6A C7A 1.391(19) . ? C7A C8A 1.34(2) . ? C8A C9A 1.40(2) . ? Cl1 C11 1.77(2) . ? Cl2 C11 1.76(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 C2 Se1 Br2 86.6(5) . . ? C2 Se1 Br1 87.1(5) . . ? Br2 Se1 Br1 173.61(11) . . ? C2 S3 C4 89.4(7) . . ? C2 N1 C9 113.5(14) . . ? C2 N1 C10 125.0(13) . . ? C9 N1 C10 121.3(13) . . ? N1 C2 S3 114.0(11) . . ? N1 C2 Se1 126.2(13) . . ? S3 C2 Se1 119.8(8) . . ? C9 C4 C5 127.6(16) . . ? C9 C4 S3 108.3(13) . . ? C5 C4 S3 124.0(13) . . ? C4 C5 C6 113.7(15) . . ? C7 C6 C5 124.3(17) . . ? C6 C7 C8 118.3(16) . . ? C7 C8 C9 117.9(16) . . ? C4 C9 C8 118.0(16) . . ? C4 C9 N1 114.7(15) . . ? C8 C9 N1 127.0(16) . . ? C2A Se1A Br1A 86.0(5) . . ? C2A Se1A Br2A 89.2(5) . . ? Br1A Se1A Br2A 175.20(12) . . ? C2A S3A C4A 92.1(7) . . ? C2A N1A C9A 113.2(14) . . ? C2A N1A C10A 124.4(14) . . ? C9A N1A C10A 122.4(15) . . ? N1A C2A S3A 112.0(12) . . ? N1A C2A Se1A 126.9(13) . . ? S3A C2A Se1A 120.8(9) . . ? C9A C4A C5A 121.5(15) . . ? C9A C4A S3A 108.8(11) . . ? C5A C4A S3A 129.5(13) . . ? C4A C5A C6A 118.4(16) . . ? C7A C6A C5A 119.4(16) . . ? C8A C7A C6A 122.8(17) . . ? C7A C8A C9A 117.8(16) . . ? C4A C9A N1A 113.9(14) . . ? C4A C9A C8A 120.1(15) . . ? N1A C9A C8A 126.0(16) . . ? Cl1 C11 Cl2 109.2(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.765 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.199 data_s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H40 Br26 N10 Se3' _chemical_formula_weight 2675.11 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' 'Se' 'Se' -0.1063 2.1121 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2770 2.3351 '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' 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 10.5396(14) _cell_length_b 17.097(3) _cell_length_c 33.115(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.671(10) _cell_angle_gamma 90.00 _cell_volume 5955.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4848 _exptl_absorpt_coefficient_mu 17.483 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.2738 _exptl_absorpt_correction_T_max 0.8446 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.68750 _diffrn_radiation_type ? _diffrn_radiation_source 'synchrotron' _diffrn_radiation_monochromator 'silicon' _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14840 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 27.46 _reflns_number_total 6296 _reflns_number_gt 4635 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0684P)^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 6296 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.118 _refine_ls_shift/su_mean 0.010 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.33663(3) 0.58469(2) 0.077633(10) 0.06216(10) Uani 1 1 d . . . Br2 Br 0.14079(2) 0.548789(14) 0.107687(7) 0.03215(7) Uani 1 1 d . . . Br3 Br -0.08520(3) 0.515330(17) 0.140680(8) 0.04341(8) Uani 1 1 d . . . Br4 Br 0.06039(2) 0.184798(17) 0.032461(7) 0.03919(8) Uani 1 1 d . . . Br5 Br 0.40559(2) 0.181149(14) 0.051141(7) 0.03148(7) Uani 1 1 d . . . Br6 Br 0.23370(2) 0.366823(14) 0.048097(7) 0.03022(6) Uani 1 1 d . . . Br7 Br -0.45086(3) 0.224553(14) 0.157149(7) 0.03480(7) Uani 1 1 d . . . Br8 Br -0.68866(2) 0.273990(15) 0.240258(7) 0.03295(7) Uani 1 1 d . . . Br9 Br -0.61925(2) 0.403772(15) 0.149827(7) 0.03278(7) Uani 1 1 d . . . Br10 Br -0.28898(2) 0.405520(14) 0.169866(7) 0.02983(6) Uani 1 1 d . . . Br11 Br -0.5000 0.469008(18) 0.2500 0.02775(9) Uani 1 2 d S . . Se1 Se 0.2500 0.2500 0.0000 0.02182(8) Uani 1 2 d S . . Se2 Se -0.46844(2) 0.340689(13) 0.195753(6) 0.02278(6) Uani 1 1 d . . . Br21 Br 0.03003(3) 0.334054(18) 0.139943(9) 0.03320(9) Uani 0.7662(5) 1 d PG A 1 N21 N 0.20952(11) 0.22761(6) 0.12692(6) 0.0376(3) Uiso 0.7662(5) 1 d PG A 1 H21A H 0.2482 0.1820 0.1276 0.045 Uiso 0.7662(5) 1 calc PR A 1 H21B H 0.2434 0.2676 0.1148 0.045 Uiso 0.7662(5) 1 calc PR A 1 N23 N 0.04313(14) 0.18192(3) 0.16260(4) 0.0376(3) Uiso 0.7662(5) 1 d PG A 1 C22 C 0.10045(9) 0.23617(3) 0.14416(3) 0.0376(3) Uiso 0.7662(5) 1 d PG A 1 C24 C 0.0999(2) 0.10405(4) 0.16623(6) 0.0376(3) Uiso 0.7662(5) 1 d PG A 1 H24A H 0.1117 0.0831 0.1392 0.056 Uiso 0.7662(5) 1 calc PR A 1 H24B H 0.0435 0.0694 0.1804 0.056 Uiso 0.7662(5) 1 calc PR A 1 H24C H 0.1824 0.1075 0.1815 0.056 Uiso 0.7662(5) 1 calc PR A 1 C25 C -0.07938(17) 0.19292(6) 0.17956(5) 0.0376(3) Uiso 0.7662(5) 1 d PG A 1 H25A H -0.1033 0.2483 0.1778 0.056 Uiso 0.7662(5) 1 calc PR A 1 H25B H -0.0737 0.1765 0.2080 0.056 Uiso 0.7662(5) 1 calc PR A 1 H25C H -0.1437 0.1614 0.1644 0.056 Uiso 0.7662(5) 1 calc PR A 1 Br31 Br -0.09136(18) 0.18710(12) 0.19959(7) 0.1200(8) Uani 0.2338(5) 1 d PG A 2 N31 N 0.1042(4) 0.0945(3) 0.18344(16) 0.0376(3) Uiso 0.2338(5) 1 d PG A 2 H31A H 0.1741 0.0796 0.1724 0.045 Uiso 0.2338(5) 1 calc PR A 2 H31B H 0.0683 0.0636 0.2007 0.045 Uiso 0.2338(5) 1 calc PR A 2 N33 N 0.0973(3) 0.2126(3) 0.14938(12) 0.0376(3) Uiso 0.2338(5) 1 d PG A 2 C32 C 0.0530(2) 0.1634(2) 0.17405(10) 0.0376(3) Uiso 0.2338(5) 1 d PG A 2 C34 C 0.2119(4) 0.1934(5) 0.12878(17) 0.0376(3) Uiso 0.2338(5) 1 d PG A 2 H34A H 0.2871 0.2107 0.1453 0.056 Uiso 0.2338(5) 1 calc PR A 2 H34B H 0.2093 0.2199 0.1025 0.056 Uiso 0.2338(5) 1 calc PR A 2 H34C H 0.2161 0.1367 0.1247 0.056 Uiso 0.2338(5) 1 calc PR A 2 C35 C 0.0412(5) 0.2891(3) 0.14130(16) 0.0376(3) Uiso 0.2338(5) 1 d PG A 2 H35A H -0.0475 0.2828 0.1311 0.056 Uiso 0.2338(5) 1 calc PR A 2 H35B H 0.0887 0.3163 0.1210 0.056 Uiso 0.2338(5) 1 calc PR A 2 H35C H 0.0446 0.3198 0.1663 0.056 Uiso 0.2338(5) 1 calc PR A 2 Br41 Br 0.25150(6) -0.24051(3) 0.059986(17) 0.04730(17) Uani 0.4942(3) 1 d PG B 1 N41 N 0.05845(16) -0.13954(11) 0.06446(11) 0.0489(5) Uiso 0.4942(3) 1 d PG B 1 H41A H 0.0176 -0.0947 0.0628 0.059 Uiso 0.4942(3) 1 calc PR B 1 H41B H 0.0191 -0.1820 0.0720 0.059 Uiso 0.4942(3) 1 calc PR B 1 N43 N 0.2451(2) -0.08501(4) 0.04443(7) 0.0489(5) Uiso 0.4942(3) 1 d PG B 1 C42 C 0.17909(15) -0.14319(5) 0.05566(6) 0.0489(5) Uiso 0.4942(3) 1 d PG B 1 C44 C 0.1876(3) -0.00730(6) 0.04130(11) 0.0489(5) Uiso 0.4942(3) 1 d PG B 1 H44A H 0.1488 0.0003 0.0139 0.073 Uiso 0.4942(3) 1 calc PR B 1 H44B H 0.2531 0.0325 0.0470 0.073 Uiso 0.4942(3) 1 calc PR B 1 H44C H 0.1221 -0.0027 0.0609 0.073 Uiso 0.4942(3) 1 calc PR B 1 C45 C 0.3757(3) -0.09226(9) 0.03332(9) 0.0489(5) Uiso 0.4942(3) 1 d PG B 1 H45A H 0.4016 -0.1473 0.0348 0.073 Uiso 0.4942(3) 1 calc PR B 1 H45B H 0.4314 -0.0613 0.0520 0.073 Uiso 0.4942(3) 1 calc PR B 1 H45C H 0.3823 -0.0731 0.0056 0.073 Uiso 0.4942(3) 1 calc PR B 1 Br51 Br 0.42349(14) -0.09041(8) 0.02293(5) 0.1108(6) Uani 0.2980(3) 1 d PG C 2 N51 N 0.2453(3) 0.01949(19) 0.03054(18) 0.0489(5) Uiso 0.2980(3) 1 d PG C 2 H51A H 0.1721 0.0399 0.0364 0.059 Uiso 0.2980(3) 1 calc PR C 2 H51B H 0.3046 0.0494 0.0211 0.059 Uiso 0.2980(3) 1 calc PR C 2 N53 N 0.18676(19) -0.1049(3) 0.04938(12) 0.0489(5) Uiso 0.2980(3) 1 d PG C 2 C52 C 0.26638(17) -0.05625(18) 0.03589(10) 0.0489(5) Uiso 0.2980(3) 1 d PG C 2 C54 C 0.0611(2) -0.0778(4) 0.05940(17) 0.0489(5) Uiso 0.2980(3) 1 d PG C 2 H54A H 0.0692 -0.0460 0.0841 0.073 Uiso 0.2980(3) 1 calc PR C 2 H54B H 0.0064 -0.1229 0.0638 0.073 Uiso 0.2980(3) 1 calc PR C 2 H54C H 0.0234 -0.0461 0.0370 0.073 Uiso 0.2980(3) 1 calc PR C 2 C55 C 0.2158(3) -0.1871(3) 0.05650(17) 0.0489(5) Uiso 0.2980(3) 1 d PG C 2 H55A H 0.2556 -0.2088 0.0330 0.073 Uiso 0.2980(3) 1 calc PR C 2 H55B H 0.1372 -0.2156 0.0607 0.073 Uiso 0.2980(3) 1 calc PR C 2 H55C H 0.2744 -0.1922 0.0806 0.073 Uiso 0.2980(3) 1 calc PR C 2 Br61 Br 0.13606(15) 0.01215(8) 0.04292(4) 0.0523(5) Uani 0.2034(3) 1 d PG D 3 N61 N 0.3600(3) -0.0480(3) 0.0245(2) 0.0489(5) Uiso 0.2034(3) 1 d PG D 3 H61A H 0.4188 -0.0837 0.0216 0.059 Uiso 0.2034(3) 1 calc PR D 3 H61B H 0.3741 0.0010 0.0179 0.059 Uiso 0.2034(3) 1 calc PR D 3 N63 N 0.2198(5) -0.13735(14) 0.0493(2) 0.0489(5) Uiso 0.2034(3) 1 d PG D 3 C62 C 0.2501(3) -0.06792(17) 0.03886(15) 0.0489(5) Uiso 0.2034(3) 1 d PG D 3 C64 C 0.3112(8) -0.2010(2) 0.0464(3) 0.0489(5) Uiso 0.2034(3) 1 d PG D 3 H64A H 0.2774 -0.2397 0.0266 0.073 Uiso 0.2034(3) 1 calc PR D 3 H64B H 0.3261 -0.2261 0.0729 0.073 Uiso 0.2034(3) 1 calc PR D 3 H64C H 0.3916 -0.1801 0.0376 0.073 Uiso 0.2034(3) 1 calc PR D 3 C65 C 0.0960(6) -0.15736(14) 0.0632(2) 0.0489(5) Uiso 0.2034(3) 1 d PG D 3 H65A H 0.0482 -0.1094 0.0678 0.073 Uiso 0.2034(3) 1 calc PR D 3 H65B H 0.1070 -0.1869 0.0886 0.073 Uiso 0.2034(3) 1 calc PR D 3 H65C H 0.0492 -0.1893 0.0427 0.073 Uiso 0.2034(3) 1 calc PR D 3 Br71 Br -0.30106(6) 0.01802(4) 0.23125(2) 0.04563(19) Uani 0.4382(4) 1 d PG . 1 N71 N -0.46866(17) -0.09477(10) 0.24581(11) 0.0343(5) Uiso 0.4382(4) 1 d PG . 1 H71A H -0.5408 -0.1159 0.2522 0.041 Uiso 0.4382(4) 1 calc PR . 1 H71B H -0.4052 -0.1248 0.2394 0.041 Uiso 0.4382(4) 1 calc PR . 1 N73 N -0.54189(10) 0.03122(15) 0.25445(7) 0.0343(5) Uiso 0.4382(4) 1 d PG . 1 C72 C -0.45566(9) -0.01775(10) 0.24570(6) 0.0343(5) Uiso 0.4382(4) 1 d PG . 1 C74 C -0.66479(13) 0.0026(2) 0.26629(11) 0.0343(5) Uiso 0.4382(4) 1 d PG . 1 H74A H -0.6937 -0.0402 0.2483 0.051 Uiso 0.4382(4) 1 calc PR . 1 H74B H -0.7270 0.0452 0.2642 0.051 Uiso 0.4382(4) 1 calc PR . 1 H74C H -0.6561 -0.0163 0.2943 0.051 Uiso 0.4382(4) 1 calc PR . 1 C75 C -0.52556(16) 0.11546(14) 0.25221(11) 0.0343(5) Uiso 0.4382(4) 1 d PG . 1 H75A H -0.4677 0.1329 0.2748 0.051 Uiso 0.4382(4) 1 calc PR . 1 H75B H -0.6082 0.1412 0.2538 0.051 Uiso 0.4382(4) 1 calc PR . 1 H75C H -0.4898 0.1291 0.2265 0.051 Uiso 0.4382(4) 1 calc PR . 1 Br81 Br -0.3779(4) 0.1048(2) 0.24560(14) 0.0446(13) Uani 0.0618(4) 1 d PG . 2 N81 N -0.4632(16) -0.0428(4) 0.2421(6) 0.0343(5) Uiso 0.0618(4) 1 d PG . 2 N83 N -0.5868(10) 0.0427(10) 0.2768(5) 0.0343(5) Uiso 0.0618(4) 1 d PG . 2 C82 C -0.4901(9) 0.0270(5) 0.2566(4) 0.0343(5) Uiso 0.0618(4) 1 d PG . 2 C84 C -0.6756(16) -0.0195(13) 0.2859(8) 0.0343(5) Uiso 0.0618(4) 1 d PG . 2 H84A H -0.7520 -0.0155 0.2675 0.051 Uiso 0.0618(4) 1 calc PR . 2 H84B H -0.6993 -0.0143 0.3139 0.051 Uiso 0.0618(4) 1 calc PR . 2 H84C H -0.6352 -0.0704 0.2824 0.051 Uiso 0.0618(4) 1 calc PR . 2 C85 C -0.6158(11) 0.1210(12) 0.2907(5) 0.0343(5) Uiso 0.0618(4) 1 d PG . 2 H85A H -0.5451 0.1562 0.2856 0.051 Uiso 0.0618(4) 1 calc PR . 2 H85B H -0.6282 0.1197 0.3197 0.051 Uiso 0.0618(4) 1 calc PR . 2 H85C H -0.6935 0.1399 0.2760 0.051 Uiso 0.0618(4) 1 calc PR . 2 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 Br1 0.04720(18) 0.0840(2) 0.05674(17) 0.01021(16) 0.01446(14) -0.02444(16) Br2 0.03014(13) 0.03336(12) 0.03341(11) 0.00445(10) 0.00564(10) -0.00013(10) Br3 0.04195(16) 0.04310(14) 0.04544(14) 0.00477(12) 0.00490(12) 0.00110(12) Br4 0.02656(13) 0.05981(16) 0.03199(12) -0.00226(11) 0.00800(10) -0.00400(12) Br5 0.02765(12) 0.04073(12) 0.02524(10) 0.00269(9) -0.00474(9) 0.01050(10) Br6 0.03051(13) 0.03487(11) 0.02523(10) -0.00534(9) 0.00144(9) 0.00494(10) Br7 0.03845(14) 0.03504(12) 0.03049(11) -0.00978(9) -0.00105(10) 0.00399(11) Br8 0.02478(12) 0.04012(12) 0.03299(11) -0.00354(10) -0.00557(10) -0.00111(10) Br9 0.02521(12) 0.04315(13) 0.02915(11) 0.00644(10) -0.00472(10) 0.00303(10) Br10 0.01937(12) 0.04158(12) 0.02895(11) 0.00028(10) 0.00472(9) 0.00191(10) Br11 0.02930(17) 0.02628(14) 0.02803(15) 0.000 0.00466(13) 0.000 Se1 0.01651(15) 0.03041(15) 0.01873(13) 0.00045(12) 0.00258(12) 0.00136(13) Se2 0.01721(11) 0.02748(10) 0.02359(10) -0.00135(8) 0.00094(8) 0.00147(9) Br21 0.03037(17) 0.03184(15) 0.03811(15) 0.00497(13) 0.00788(13) 0.00352(14) Br31 0.0780(12) 0.0980(13) 0.1902(19) 0.0545(13) 0.0561(12) 0.0089(11) Br41 0.0376(3) 0.0528(3) 0.0517(3) -0.0033(3) 0.0037(3) 0.0069(3) Br51 0.0797(8) 0.0757(8) 0.1851(13) 0.0429(9) 0.0720(8) 0.0168(7) Br61 0.0588(9) 0.0405(7) 0.0571(8) 0.0069(6) -0.0001(7) 0.0052(7) Br71 0.0261(3) 0.0503(3) 0.0624(4) 0.0161(3) 0.0183(3) 0.0049(3) Br81 0.039(2) 0.035(2) 0.059(3) -0.0037(19) -0.001(2) 0.0160(18) _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 Br1 Br2 2.4270(5) . ? Br2 Br3 2.7437(5) . ? Br4 Se1 2.5820(4) . ? Br5 Se1 2.5666(3) . ? Br6 Se1 2.5673(3) . ? Br7 Se2 2.3752(4) . ? Br9 Se2 2.3861(4) . ? Br10 Se2 2.3976(4) . ? Se1 Br5 2.5666(3) 7 ? Se1 Br6 2.5673(3) 7 ? Se1 Br4 2.5820(4) 7 ? Br21 C22 1.8325 . ? N21 C22 1.3240 . ? N23 C22 1.2826 . ? N23 C25 1.4529 . ? N23 C24 1.4615 . ? Br31 C32 1.8325 . ? N31 C32 1.3240 . ? N33 C32 1.2826 . ? N33 C35 1.4529 . ? N33 C34 1.4615 . ? Br41 C42 1.8325 . ? N41 C42 1.3240 . ? N43 C42 1.2826 . ? N43 C45 1.4529 . ? N43 C44 1.4615 . ? Br51 C52 1.8325 . ? N51 C52 1.3240 . ? N53 C52 1.2826 . ? N53 C55 1.4529 . ? N53 C54 1.4615 . ? Br61 C62 1.8325 . ? N61 C62 1.3240 . ? N63 C62 1.2826 . ? N63 C65 1.4529 . ? N63 C64 1.4615 . ? Br71 C74 0.4575(11) 2_455 ? Br71 N73 1.7651(13) 2_455 ? Br71 C72 1.8325 . ? N71 C72 1.3240 . ? N73 C72 1.2826 . ? N73 C75 1.4529 . ? N73 C74 1.4615 . ? Br81 C85 1.230(10) 2_455 ? Br81 N83 1.335(11) 2_455 ? Br81 C82 1.8325 . ? Br81 C82 1.923(14) 2_455 ? Br81 Br81 2.609(9) 2_455 ? N81 C82 1.3240 . ? N83 C82 1.2826 . ? N83 C85 1.4529 . ? N83 C84 1.4615 . ? 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 Br1 Br2 Br3 177.193(15) . . ? Br5 Se1 Br5 180.000(12) . 7 ? Br5 Se1 Br6 89.269(11) . 7 ? Br5 Se1 Br6 90.731(11) 7 7 ? Br5 Se1 Br6 90.731(11) . . ? Br5 Se1 Br6 89.269(11) 7 . ? Br6 Se1 Br6 180.000(10) 7 . ? Br5 Se1 Br4 89.651(12) . 7 ? Br5 Se1 Br4 90.349(12) 7 7 ? Br6 Se1 Br4 89.616(12) 7 7 ? Br6 Se1 Br4 90.384(12) . 7 ? Br5 Se1 Br4 90.349(12) . . ? Br5 Se1 Br4 89.651(12) 7 . ? Br6 Se1 Br4 90.384(12) 7 . ? Br6 Se1 Br4 89.616(12) . . ? Br4 Se1 Br4 180.000(10) 7 . ? Br7 Se2 Br9 96.117(14) . . ? Br7 Se2 Br10 95.943(14) . . ? Br9 Se2 Br10 94.112(14) . . ? C22 N23 C25 123.2 . . ? C22 N23 C24 119.7 . . ? C25 N23 C24 117.1 . . ? N23 C22 N21 125.0 . . ? N23 C22 Br21 119.7 . . ? N21 C22 Br21 115.3 . . ? C32 N33 C35 123.2 . . ? C32 N33 C34 119.7 . . ? C35 N33 C34 117.1 . . ? N33 C32 N31 125.0 . . ? N33 C32 Br31 119.7 . . ? N31 C32 Br31 115.3 . . ? C42 N43 C45 123.2 . . ? C42 N43 C44 119.7 . . ? C45 N43 C44 117.1 . . ? N43 C42 N41 125.0 . . ? N43 C42 Br41 119.7 . . ? N41 C42 Br41 115.3 . . ? C52 N53 C55 123.2 . . ? C52 N53 C54 119.7 . . ? C55 N53 C54 117.1 . . ? N53 C52 N51 125.0 . . ? N53 C52 Br51 119.7 . . ? N51 C52 Br51 115.3 . . ? C62 N63 C65 123.2 . . ? C62 N63 C64 119.7 . . ? C65 N63 C64 117.1 . . ? N63 C62 N61 125.0 . . ? N63 C62 Br61 119.7 . . ? N61 C62 Br61 115.3 . . ? C74 Br71 N73 42.59(10) 2_455 2_455 ? C74 Br71 C72 15.94(11) 2_455 . ? N73 Br71 C72 26.8 2_455 . ? C72 N73 C75 123.2 . . ? C72 N73 C74 119.7 . . ? C75 N73 C74 117.1 . . ? N73 C72 N71 125.0 . . ? N73 C72 Br71 119.7 . . ? N71 C72 Br71 115.3 . . ? C85 Br81 N83 68.9(7) 2_455 2_455 ? C85 Br81 C82 111.3(6) 2_455 . ? N83 Br81 C82 51.2(8) 2_455 . ? C85 Br81 C82 97.1(8) 2_455 2_455 ? N83 Br81 C82 41.7(3) 2_455 2_455 ? C82 Br81 C82 14.2(8) . 2_455 ? C85 Br81 Br81 96.7(6) 2_455 2_455 ? N83 Br81 Br81 79.6(5) 2_455 2_455 ? C82 Br81 Br81 47.4(4) . 2_455 ? C82 Br81 Br81 44.6(2) 2_455 2_455 ? C82 N83 C85 123.2 . . ? C82 N83 C84 119.7 . . ? C85 N83 C84 117.1 . . ? N83 C82 N81 125.0 . . ? N83 C82 Br81 119.7 . . ? N81 C82 Br81 115.3 . . ? _diffrn_measured_fraction_theta_max 0.837 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.837 _refine_diff_density_max 2.320 _refine_diff_density_min -1.954 _refine_diff_density_rms 0.204