# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1683 data_p _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 Cl2 N O2 S2' _chemical_formula_weight 284.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 '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 7.516(2) _cell_length_b 7.649(2) _cell_length_c 18.973(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.20(2) _cell_angle_gamma 90.00 _cell_volume 1086.3(4) _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 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.958 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8315 _exptl_absorpt_correction_T_max 0.8315 _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 2033 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1878 _reflns_number_gt 1515 _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^)+(0.0050P)^2^+12.3719P] 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 0.0027(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1878 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.4695(2) 0.9240(2) 0.38031(9) 0.0287(5) Uani 1 d . A 1 Cl2 Cl 0.2174(3) 1.2318(3) 0.33688(10) 0.0326(5) Uani 1 d . B 1 N1 N 0.6034(8) 0.6054(7) 0.3811(3) 0.0236(13) Uani 1 d . A 1 C2 C 0.5773(9) 0.7496(9) 0.4158(4) 0.0230(15) Uani 1 d . A 1 S3 S 0.6577(2) 0.7483(2) 0.50236(9) 0.0248(5) Uani 1 d . A 1 C4 C 0.7311(9) 0.5349(10) 0.4923(4) 0.0259(16) Uani 1 d . A 1 C5 C 0.8153(10) 0.4275(11) 0.5432(4) 0.0275(17) Uani 1 d . A 1 C6 C 0.8630(10) 0.2635(10) 0.5208(4) 0.0288(17) Uani 1 d . A 1 C7 C 0.8328(11) 0.2087(10) 0.4531(4) 0.0313(18) Uani 1 d . A 1 C8 C 0.7466(10) 0.3157(10) 0.4017(4) 0.0279(17) Uani 1 d . A 1 C9 C 0.6960(9) 0.4782(9) 0.4240(4) 0.0242(16) Uani 1 d . A 1 C10 C 0.5408(13) 0.5753(12) 0.3067(4) 0.0337(19) Uani 1 d . A 1 H5 H 0.829(11) 0.458(12) 0.581(5) 0.04(3) Uiso 1 d . C 1 H6 H 0.915(9) 0.199(10) 0.551(4) 0.015(19) Uiso 1 d . D 1 H7 H 0.855(8) 0.097(9) 0.441(3) 0.007(15) Uiso 1 d . E 1 H8 H 0.716(10) 0.270(11) 0.356(4) 0.04(2) Uiso 1 d . F 1 H10A H 0.447(16) 0.686(17) 0.289(6) 0.10(4) Uiso 1 d . G 1 H10B H 0.634(10) 0.577(11) 0.283(4) 0.03(2) Uiso 1 d . H 1 H10C H 0.480(14) 0.482(15) 0.301(6) 0.07(4) Uiso 1 d . I 1 S1 S 0.0095(3) 1.4051(3) 0.22653(10) 0.0310(5) Uani 1 d . J 2 O1 O 0.1276(9) 1.3867(11) 0.1727(3) 0.062(2) Uani 1 d . J 2 O2 O -0.1393(8) 1.2922(8) 0.2225(4) 0.0524(18) Uani 1 d . J 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 Cl1 0.0328(10) 0.0219(9) 0.0304(9) 0.0038(8) -0.0021(7) 0.0027(8) Cl2 0.0393(10) 0.0317(10) 0.0258(9) -0.0027(8) -0.0027(8) 0.0069(9) N1 0.030(3) 0.018(3) 0.023(3) -0.003(3) 0.001(3) -0.004(3) C2 0.021(3) 0.019(4) 0.029(4) 0.002(3) 0.002(3) -0.007(3) S3 0.0305(10) 0.0198(9) 0.0238(9) -0.0029(7) -0.0001(7) 0.0026(8) C4 0.026(4) 0.023(4) 0.029(4) -0.008(3) 0.008(3) 0.001(3) C5 0.023(4) 0.036(5) 0.023(4) 0.001(4) 0.000(3) 0.006(3) C6 0.030(4) 0.020(4) 0.036(4) 0.007(4) 0.001(3) 0.004(3) C7 0.034(4) 0.021(4) 0.042(5) 0.000(3) 0.015(4) 0.000(3) C8 0.028(4) 0.026(4) 0.030(4) -0.006(3) 0.006(3) -0.003(3) C9 0.026(4) 0.024(4) 0.022(4) 0.004(3) -0.001(3) -0.001(3) C10 0.049(5) 0.032(5) 0.020(4) -0.009(4) 0.004(4) -0.008(4) S1 0.0332(10) 0.0305(11) 0.0290(10) 0.0030(8) 0.0011(8) 0.0026(9) O1 0.060(4) 0.088(6) 0.040(4) 0.024(4) 0.017(3) 0.023(4) O2 0.041(4) 0.042(4) 0.069(4) 0.017(3) -0.019(3) -0.007(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 Cl1 C2 1.670(7) . ? N1 C2 1.309(9) . ? N1 C9 1.411(9) . ? N1 C10 1.464(9) . ? C2 S3 1.697(7) . ? S3 C4 1.739(7) . ? C4 C9 1.370(10) . ? C4 C5 1.377(11) . ? C5 C6 1.382(11) . ? C6 C7 1.351(11) . ? C7 C8 1.388(11) . ? C8 C9 1.378(10) . ? S1 O2 1.410(6) . ? S1 O1 1.420(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 112.3(6) . . ? C2 N1 C10 124.6(7) . . ? C9 N1 C10 123.1(6) . . ? N1 C2 Cl1 124.0(5) . . ? N1 C2 S3 115.2(5) . . ? Cl1 C2 S3 120.8(4) . . ? C2 S3 C4 89.3(4) . . ? C9 C4 C5 120.8(7) . . ? C9 C4 S3 111.4(6) . . ? C5 C4 S3 127.9(6) . . ? C4 C5 C6 116.2(7) . . ? C7 C6 C5 123.3(8) . . ? C6 C7 C8 120.9(7) . . ? C9 C8 C7 116.1(7) . . ? C4 C9 C8 122.8(7) . . ? C4 C9 N1 111.8(6) . . ? C8 C9 N1 125.4(7) . . ? O2 S1 O1 116.4(5) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.524 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.126 data_s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Cl6 N4 Se2' _chemical_formula_weight 514.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0267(10) _cell_length_b 16.367(2) _cell_length_c 18.116(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.80(2) _cell_angle_gamma 90.00 _cell_volume 1770.5(4) _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 'colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 5.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3637 _exptl_absorpt_correction_T_max 0.5167 _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 3388 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3078 _reflns_number_gt 1994 _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^)+(0.0663P)^2^+5.7803P] 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 3078 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.006 _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 Se1A Se 0.64557(5) 0.708322(17) 0.673064(16) 0.02750(8) Uani 0.9032(3) d P . . Se1B Se 0.5272(5) 0.7096(2) 0.66438(18) 0.0432(7) Uiso 0.0968(3) d P . . Se2A Se 1.01910(5) 0.719764(17) 0.671035(15) 0.02737(8) Uani 0.9032(3) d P . . Se2B Se 1.1664(5) 0.71321(19) 0.67242(17) 0.0398(7) Uiso 0.0968(3) d P . . Cl2 Cl 0.56655(13) 0.61321(4) 0.57125(4) 0.0458(2) Uani 1 d . . . Cl3 Cl 0.62937(12) 0.80608(4) 0.77710(4) 0.0378(2) Uani 1 d . . . Cl4 Cl 1.14316(12) 0.61582(4) 0.74929(4) 0.0417(2) Uani 1 d . . . Cl5 Cl 0.98514(11) 0.84598(4) 0.56659(4) 0.03590(19) Uani 1 d . . . Cl1 Cl 1.18139(12) 0.54681(4) 0.94797(4) 0.03671(19) Uani 1 d . . . N1 N 1.0686(4) 0.42857(13) 0.85679(13) 0.0354(7) Uani 1 d . . . H1A H 0.9829 0.4019 0.8224 0.043 Uiso 1 calc R . . H1B H 1.1988 0.4089 0.8748 0.043 Uiso 1 calc R . . C2 C 1.0014(4) 0.49833(15) 0.88142(13) 0.0269(7) Uani 1 d . . . N3 N 0.8116(3) 0.53252(12) 0.85830(12) 0.0283(6) Uani 1 d . . . C4 C 0.7401(4) 0.61144(16) 0.88493(16) 0.0366(8) Uani 1 d . . . H4A H 0.8632 0.6362 0.9173 0.055 Uiso 1 calc R . . H4B H 0.6144 0.6033 0.9124 0.055 Uiso 1 calc R . . H4C H 0.6954 0.6471 0.8427 0.055 Uiso 1 calc R . . C5 C 0.6621(4) 0.49525(17) 0.79700(16) 0.0385(9) Uani 1 d . . . H5A H 0.7391 0.4910 0.7535 0.058 Uiso 1 calc R . . H5B H 0.5295 0.5289 0.7853 0.058 Uiso 1 calc R . . H5C H 0.6187 0.4412 0.8117 0.058 Uiso 1 calc R . . Cl11 Cl 1.11740(13) 0.53981(4) 0.42339(4) 0.0453(2) Uani 1 d . . . N11 N 1.0984(4) 0.68173(14) 0.48307(12) 0.0378(7) Uani 1 d . . . H11A H 1.0385 0.7284 0.4920 0.045 Uiso 1 calc R . . H11B H 1.2311 0.6692 0.5053 0.045 Uiso 1 calc R . . C12 C 0.9888(4) 0.63032(16) 0.43620(14) 0.0314(7) Uani 1 d . . . N13 N 0.7906(4) 0.64383(12) 0.40057(12) 0.0315(6) Uani 1 d . . . C14 C 0.6887(4) 0.72459(16) 0.40769(16) 0.0367(8) Uani 1 d . . . H14A H 0.6868 0.7369 0.4600 0.055 Uiso 1 calc R . . H14B H 0.5365 0.7244 0.3820 0.055 Uiso 1 calc R . . H14C H 0.7754 0.7657 0.3858 0.055 Uiso 1 calc R . . C15 C 0.6726(5) 0.58681(18) 0.34568(18) 0.0506(10) Uani 1 d . . . H15A H 0.7243 0.5316 0.3572 0.076 Uiso 1 calc R . . H15B H 0.7030 0.6014 0.2961 0.076 Uiso 1 calc R . . H15C H 0.5127 0.5899 0.3476 0.076 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 Se1A 0.02461(13) 0.02577(12) 0.03096(14) 0.00140(13) -0.00045(12) 0.00094(13) Se2A 0.02590(13) 0.03000(13) 0.02581(13) 0.00429(13) 0.00207(11) -0.00063(13) Cl2 0.0444(4) 0.0399(4) 0.0494(4) -0.0092(3) -0.0069(4) 0.0093(3) Cl3 0.0399(4) 0.0354(3) 0.0375(4) -0.0008(3) 0.0029(3) 0.0044(3) Cl4 0.0349(3) 0.0460(4) 0.0439(4) 0.0160(3) 0.0048(3) 0.0087(3) Cl5 0.0376(4) 0.0292(3) 0.0369(4) 0.0009(3) -0.0092(3) -0.0020(3) Cl1 0.0399(4) 0.0392(3) 0.0283(3) -0.0015(3) -0.0054(3) -0.0128(3) N1 0.0240(11) 0.0310(11) 0.0468(14) -0.0043(11) -0.0114(11) -0.0021(10) C2 0.0302(13) 0.0275(12) 0.0209(12) -0.0026(11) -0.0043(11) -0.0104(11) N3 0.0295(11) 0.0216(9) 0.0308(11) 0.0030(9) -0.0066(10) -0.0007(9) C4 0.0272(13) 0.0341(14) 0.0490(16) 0.0005(13) 0.0065(13) 0.0034(12) C5 0.0295(14) 0.0394(15) 0.0430(16) 0.0030(14) -0.0075(13) 0.0016(13) Cl11 0.0529(4) 0.0372(3) 0.0466(4) 0.0023(3) 0.0099(3) 0.0147(3) N11 0.0314(12) 0.0444(13) 0.0325(12) -0.0087(11) -0.0145(11) 0.0106(11) C12 0.0366(14) 0.0290(13) 0.0317(13) 0.0051(12) 0.0151(11) 0.0027(12) N13 0.0352(12) 0.0275(10) 0.0315(11) 0.0002(10) 0.0038(10) 0.0025(10) C14 0.0272(13) 0.0372(14) 0.0426(15) 0.0018(13) -0.0060(12) 0.0100(12) C15 0.0329(15) 0.0469(16) 0.067(2) -0.0160(16) -0.0121(16) -0.0111(14) _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 Se1A Se1B 0.710(3) . ? Se1A Se2A 2.2642(5) . ? Se1A Cl2 2.4112(8) . ? Se1A Cl3 2.4843(8) . ? Se1B Se2B 2.199(5) 1_455 ? Se1B Cl2 2.345(3) . ? Se1B Cl3 2.589(3) . ? Se2A Se2B 0.891(3) . ? Se2A Cl4 2.2750(8) . ? Se2B Cl4 2.134(3) . ? Se2B Se1B 2.199(5) 1_655 ? Cl1 C2 1.704(2) . ? N1 C2 1.310(3) . ? C2 N3 1.292(3) . ? N3 C4 1.464(3) . ? N3 C5 1.465(3) . ? Cl11 C12 1.702(3) . ? N11 C12 1.309(3) . ? C12 N13 1.297(3) . ? N13 C14 1.471(3) . ? N13 C15 1.474(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Se1B Se1A Se2A 165.0(3) . . ? Se1B Se1A Cl2 76.2(3) . . ? Se2A Se1A Cl2 97.74(3) . . ? Se1B Se1A Cl3 90.4(3) . . ? Se2A Se1A Cl3 95.77(3) . . ? Cl2 Se1A Cl3 166.44(3) . . ? Se1A Se1B Se2B 163.6(4) . 1_455 ? Se1A Se1B Cl2 86.7(3) . . ? Se2B Se1B Cl2 105.27(15) 1_455 . ? Se1A Se1B Cl3 73.6(2) . . ? Se2B Se1B Cl3 93.60(14) 1_455 . ? Cl2 Se1B Cl3 160.27(15) . . ? Se2B Se2A Se1A 168.1(2) . . ? Se2B Se2A Cl4 69.5(2) . . ? Se1A Se2A Cl4 99.87(3) . . ? Se2A Se2B Cl4 87.4(2) . . ? Se2A Se2B Se1B 172.4(3) . 1_655 ? Cl4 Se2B Se1B 100.15(15) . 1_655 ? Se1B Cl2 Se1A 17.09(8) . . ? Se1A Cl3 Se1B 15.91(7) . . ? Se2B Cl4 Se2A 23.04(8) . . ? N3 C2 N1 124.6(2) . . ? N3 C2 Cl1 118.59(19) . . ? N1 C2 Cl1 116.77(18) . . ? C2 N3 C4 124.2(2) . . ? C2 N3 C5 119.5(2) . . ? C4 N3 C5 116.1(2) . . ? N13 C12 N11 124.2(2) . . ? N13 C12 Cl11 119.08(19) . . ? N11 C12 Cl11 116.67(19) . . ? C12 N13 C14 118.5(2) . . ? C12 N13 C15 123.7(2) . . ? C14 N13 C15 117.3(2) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 1.206 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.159 data_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H18 Cl10 N4 Se' _chemical_formula_weight 591.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 '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 mn21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y, z+1/2' '-x, y, z' _cell_length_a 13.974(3) _cell_length_b 7.633(2) _cell_length_c 10.230(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1091.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.944 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5265 _exptl_absorpt_correction_T_max 0.5905 _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 1058 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1058 _reflns_number_gt 775 _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^)+(0.0723P)^2^+2.4431P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(6) _refine_ls_number_reflns 1058 _refine_ls_number_parameters 109 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.066 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.74525(17) 0.7573(3) 0.40896(17) 0.0950(8) Uani 0.50 d PD A 1 C4B C 0.74525(17) 0.7573(3) 0.40896(17) 0.0950(8) Uani 0.50 d P A 1 N1A N 0.8551(3) 0.8788(6) 0.2665(5) 0.0284(12) Uiso 0.25 d PD A 1 C1A C 0.8551(3) 0.8788(6) 0.2665(5) 0.0284(12) Uiso 0.25 d P A 1 N1B N 0.6438(4) 0.6299(7) 0.2892(6) 0.0466(16) Uiso 0.25 d PD A 1 C1B C 0.6438(4) 0.6299(7) 0.2892(6) 0.0466(16) Uiso 0.25 d P A 1 C2A C 0.7749(3) 0.7894(5) 0.2621(3) 0.0124(9) Uiso 0.25 d PD A 1 N2A N 0.7749(3) 0.7894(5) 0.2621(3) 0.0124(9) Uiso 0.25 d P A 1 C2B C 0.7193(3) 0.7341(6) 0.2688(4) 0.0280(12) Uiso 0.25 d PD A 1 N2B N 0.7193(3) 0.7341(6) 0.2688(4) 0.0280(12) Uiso 0.25 d P A 1 N3A N 0.7282(4) 0.7431(8) 0.1654(4) 0.056(2) Uiso 0.25 d PD A 1 C3A C 0.7282(4) 0.7431(8) 0.1654(4) 0.056(2) Uiso 0.25 d P A 1 N3B N 0.7545(4) 0.7717(10) 0.1619(4) 0.094(3) Uiso 0.25 d PD A 1 C3B C 0.7545(4) 0.7717(10) 0.1619(4) 0.094(3) Uiso 0.25 d P A 1 C4A C 0.73241(12) 0.7350(2) 0.01920(13) 0.0503(4) Uani 0.50 d PD A 1 Cl1B Cl 0.73241(12) 0.7350(2) 0.01920(13) 0.0503(4) Uani 0.50 d P A 1 C5A C 0.6328(4) 0.6265(7) 0.1914(6) 0.0499(17) Uiso 0.25 d PD A 1 N5A N 0.6328(4) 0.6265(7) 0.1914(6) 0.0499(17) Uiso 0.25 d P A 1 C5B C 0.8512(3) 0.8812(6) 0.1904(5) 0.0284(13) Uiso 0.25 d PD A 1 N5B N 0.8512(3) 0.8812(6) 0.1904(5) 0.0284(13) Uiso 0.25 d P A 1 Se1 Se 0.5000 0.66127(4) 0.71409(12) 0.02488(8) Uani 1 d S . 2 Cl2 Cl 0.66985(4) 0.66302(9) 0.7165(2) 0.03889(17) Uani 1 d . B 2 Cl3 Cl 0.5000 0.45669(18) 0.87717(14) 0.0578(4) Uani 1 d S C 2 Cl4 Cl 0.5000 0.9036(2) 0.89288(14) 0.0592(4) Uani 1 d S D 2 Cl5 Cl 0.5000 0.8995(2) 0.54144(15) 0.0606(5) Uani 1 d S E 2 Cl6 Cl 0.5000 0.4564(2) 0.55929(16) 0.0665(5) Uani 1 d S F 2 Cl7 Cl 0.89568(7) 0.84558(14) 0.7075(3) 0.0963(4) Uani 1 d . G 3 C6 C 1.0000 0.9677(6) 0.7297(7) 0.0478(14) Uani 1 d S . 3 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 Cl1A 0.1082(14) 0.1228(15) 0.0541(10) -0.0072(11) 0.0113(11) 0.0588(12) C4B 0.1082(14) 0.1228(15) 0.0541(10) -0.0072(11) 0.0113(11) 0.0588(12) C4A 0.0567(8) 0.0505(8) 0.0437(7) -0.0122(7) -0.0128(7) -0.0046(8) Cl1B 0.0567(8) 0.0505(8) 0.0437(7) -0.0122(7) -0.0128(7) -0.0046(8) Se1 0.02010(14) 0.02867(15) 0.02587(14) 0.0006(5) 0.000 0.000 Cl2 0.0213(3) 0.0526(3) 0.0428(3) 0.0069(10) 0.0002(11) 0.0065(3) Cl3 0.0432(7) 0.0639(8) 0.0662(8) 0.0439(6) 0.000 0.000 Cl4 0.0345(6) 0.0778(8) 0.0653(8) -0.0427(7) 0.000 0.000 Cl5 0.0370(7) 0.0664(8) 0.0783(9) 0.0444(7) 0.000 0.000 Cl6 0.0511(8) 0.0741(10) 0.0744(10) -0.0393(8) 0.000 0.000 Cl7 0.0639(5) 0.0810(6) 0.1442(10) 0.0262(14) -0.0320(13) -0.0272(5) C6 0.036(2) 0.063(3) 0.044(3) 0.009(4) 0.000 0.000 _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 Cl1A C2B 1.489(4) . ? Cl1A C2A 1.578(4) . ? Cl1A N1B 2.111(6) . ? N1A C5B 0.781(7) . ? N1A C2A 1.313(6) . ? N1B C5A 1.013(9) . ? N1B C2B 1.338(7) . ? C2A C2B 0.886(6) . ? C2A N3B 1.073(6) . ? C2A N3A 1.236(6) . ? C2A C5B 1.472(6) . ? C2B N3A 1.067(5) . ? C2B N3B 1.233(6) . ? C2B C5A 1.663(7) . ? N3A C4A 1.498(4) . ? N3A C5A 1.625(7) . ? N3B C4A 1.518(5) . ? N3B C5B 1.615(7) . ? Se1 Cl6 2.2255(19) . ? Se1 Cl3 2.2850(17) . ? Se1 Cl2 2.3736(8) . ? Se1 Cl2 2.3736(8) 4_655 ? Se1 Cl5 2.5347(18) . ? Se1 Cl4 2.6011(18) . ? Cl7 C6 1.745(3) . ? C6 Cl7 1.745(3) 4_755 ? 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 C2B Cl1A C2A 33.4(2) . . ? C2B Cl1A N1B 39.0(2) . . ? C2A Cl1A N1B 72.2(2) . . ? C5B N1A C2A 85.3(5) . . ? C5A N1B C2B 88.9(5) . . ? C5A N1B Cl1A 133.4(5) . . ? C2B N1B Cl1A 44.5(2) . . ? C2B C2A N3B 77.3(5) . . ? C2B C2A N3A 57.6(4) . . ? N3B C2A N3A 19.8(4) . . ? C2B C2A N1A 173.0(5) . . ? N3B C2A N1A 109.0(5) . . ? N3A C2A N1A 128.8(4) . . ? C2B C2A C5B 154.1(4) . . ? N3B C2A C5B 77.1(4) . . ? N3A C2A C5B 96.9(4) . . ? N1A C2A C5B 32.0(3) . . ? C2B C2A Cl1A 67.8(3) . . ? N3B C2A Cl1A 145.2(5) . . ? N3A C2A Cl1A 125.4(4) . . ? N1A C2A Cl1A 105.8(3) . . ? C5B C2A Cl1A 137.6(3) . . ? C2A C2B N3A 77.9(5) . . ? C2A C2B N3B 58.1(4) . . ? N3A C2B N3B 19.8(4) . . ? C2A C2B N1B 170.4(6) . . ? N3A C2B N1B 106.5(5) . . ? N3B C2B N1B 126.2(5) . . ? C2A C2B Cl1A 78.7(4) . . ? N3A C2B Cl1A 156.7(5) . . ? N3B C2B Cl1A 136.9(4) . . ? N1B C2B Cl1A 96.5(4) . . ? C2A C2B C5A 146.7(5) . . ? N3A C2B C5A 69.2(4) . . ? N3B C2B C5A 89.0(4) . . ? N1B C2B C5A 37.5(4) . . ? Cl1A C2B C5A 134.0(4) . . ? C2B N3A C2A 44.5(3) . . ? C2B N3A C4A 172.5(6) . . ? C2A N3A C4A 142.2(4) . . ? C2B N3A C5A 73.0(4) . . ? C2A N3A C5A 117.3(4) . . ? C4A N3A C5A 99.9(4) . . ? C2A N3B C2B 44.5(3) . . ? C2A N3B C4A 175.0(7) . . ? C2B N3B C4A 136.8(5) . . ? C2A N3B C5B 62.6(4) . . ? C2B N3B C5B 107.1(4) . . ? C4A N3B C5B 116.0(4) . . ? N3A C4A N3B 16.3(3) . . ? N1B C5A N3A 91.3(5) . . ? N1B C5A C2B 53.5(4) . . ? N3A C5A C2B 37.9(2) . . ? N1A C5B C2A 62.8(5) . . ? N1A C5B N3B 103.1(5) . . ? C2A C5B N3B 40.3(2) . . ? Cl6 Se1 Cl3 92.25(6) . . ? Cl6 Se1 Cl2 90.65(5) . . ? Cl3 Se1 Cl2 89.79(5) . . ? Cl6 Se1 Cl2 90.65(5) . 4_655 ? Cl3 Se1 Cl2 89.79(5) . 4_655 ? Cl2 Se1 Cl2 178.66(12) . 4_655 ? Cl6 Se1 Cl5 90.47(7) . . ? Cl3 Se1 Cl5 177.28(7) . . ? Cl2 Se1 Cl5 90.18(5) . . ? Cl2 Se1 Cl5 90.18(5) 4_655 . ? Cl6 Se1 Cl4 179.32(7) . . ? Cl3 Se1 Cl4 88.43(7) . . ? Cl2 Se1 Cl4 89.36(5) . . ? Cl2 Se1 Cl4 89.36(5) 4_655 . ? Cl5 Se1 Cl4 88.85(5) . . ? Cl7 C6 Cl7 113.3(3) . 4_755 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.643 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.112 data_n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H8 Cl6 N2 Se' _chemical_formula_weight 363.77 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 '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 nma' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.555(2) _cell_length_b 15.516(2) _cell_length_c 9.9151(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1162.3(4) _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 'colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 4.562 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3951 _exptl_absorpt_correction_T_max 0.6583 _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 2023 _diffrn_reflns_av_R_equivalents 0.2288 _diffrn_reflns_av_sigmaI/netI 0.2545 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1058 _reflns_number_gt 378 _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^)+(0.0460P)^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 1058 _refine_ls_number_parameters 61 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2377 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 0.866 _refine_ls_restrained_S_all 0.866 _refine_ls_shift/su_max 0.005 _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 0.10114(11) 0.2500 0.05977(7) 0.02718(18) Uani 1 d S . . Cl2 Cl -0.1151(4) 0.2500 -0.09725(18) 0.0566(7) Uani 1 d S . . Cl3 Cl 0.0991(2) 0.09767(7) 0.05711(15) 0.0448(4) Uani 1 d . . . Cl4 Cl 0.3075(3) 0.2500 -0.0911(2) 0.0594(8) Uani 1 d S . . Cl5 Cl 0.3294(3) 0.2500 0.2474(2) 0.0415(6) Uani 1 d S . . Cl1 Cl 0.0692(3) 0.05762(17) 0.6771(3) 0.0655(9) Uani 0.50 d P . . C4 C 0.0692(3) 0.05762(17) 0.6771(3) 0.0655(9) Uani 0.50 d P . . H4A H 0.1351 0.1113 0.6797 0.098 Uiso 0.50 calc PR . . H4B H 0.1366 0.0129 0.7222 0.098 Uiso 0.50 calc PR . . H4C H -0.0434 0.0652 0.7225 0.098 Uiso 0.50 calc PR . . N1 N 0.1127(6) 0.0855(3) 0.4171(5) 0.0486(16) Uani 0.50 d P . . H1A H 0.1153 0.0759 0.3307 0.073 Uiso 0.50 calc PR . . H1B H 0.1615 0.1317 0.4500 0.073 Uiso 0.50 calc PR . . C5 C 0.1127(6) 0.0855(3) 0.4171(5) 0.0486(16) Uani 0.50 d P . . H5A H 0.1666 0.1310 0.4701 0.073 Uiso 0.50 calc PR . . H5B H 0.0255 0.1101 0.3566 0.073 Uiso 0.50 calc PR . . H5C H 0.2033 0.0563 0.3649 0.073 Uiso 0.50 calc PR . . C2 C 0.0308(7) 0.0268(4) 0.5027(9) 0.108(3) Uani 0.50 d P . . N3 N 0.0308(7) 0.0268(4) 0.5027(9) 0.108(3) Uani 0.50 d P . . 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 0.0359(4) 0.0258(3) 0.0198(3) 0.000 0.0006(6) 0.000 Cl2 0.0835(16) 0.0525(12) 0.0338(11) 0.000 -0.0268(13) 0.000 Cl3 0.0497(7) 0.0262(6) 0.0585(7) -0.0075(8) 0.0012(12) 0.0046(8) Cl4 0.0727(16) 0.0645(15) 0.0410(13) 0.000 0.0317(11) 0.000 Cl5 0.0333(11) 0.0409(10) 0.0503(11) 0.000 -0.0002(10) 0.000 Cl1 0.0671(19) 0.0642(16) 0.0653(15) -0.0038(15) -0.0192(16) 0.0039(18) C4 0.0671(19) 0.0642(16) 0.0653(15) -0.0038(15) -0.0192(16) 0.0039(18) N1 0.033(3) 0.038(3) 0.075(3) 0.009(3) 0.001(4) -0.008(3) C5 0.033(3) 0.038(3) 0.075(3) 0.009(3) 0.001(4) -0.008(3) C2 0.038(3) 0.063(5) 0.223(8) 0.078(5) 0.042(4) 0.025(3) N3 0.038(3) 0.063(5) 0.223(8) 0.078(5) 0.042(4) 0.025(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 Cl4 2.161(2) . ? Se1 Cl2 2.257(2) . ? Se1 Cl3 2.3639(11) . ? Se1 Cl3 2.3639(11) 6_565 ? Se1 Cl5 2.537(2) . ? Cl1 C2 1.817(9) . ? N1 C2 1.391(8) . ? C2 C2 0.953(11) 5_556 ? C2 N3 0.953(11) 5_556 ? 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 Se1 Cl2 92.55(9) . . ? Cl4 Se1 Cl3 89.83(4) . . ? Cl2 Se1 Cl3 89.28(4) . . ? Cl4 Se1 Cl3 89.83(4) . 6_565 ? Cl2 Se1 Cl3 89.28(4) . 6_565 ? Cl3 Se1 Cl3 178.51(8) . 6_565 ? Cl4 Se1 Cl5 91.00(8) . . ? Cl2 Se1 Cl5 176.45(8) . . ? Cl3 Se1 Cl5 90.73(4) . . ? Cl3 Se1 Cl5 90.73(4) 6_565 . ? C2 C2 N3 0.0(13) 5_556 5_556 ? C2 C2 N1 138.8(14) 5_556 . ? N3 C2 N1 138.8(14) 5_556 . ? C2 C2 Cl1 111.2(12) 5_556 . ? N3 C2 Cl1 111.2(12) 5_556 . ? N1 C2 Cl1 109.7(4) . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.882 _refine_diff_density_max 0.610 _refine_diff_density_min -0.886 _refine_diff_density_rms 0.159