# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1587 data_global # SUBMISSION DETAILS _audit_creation_method 'manual editing of SHELXL template' _publ_contact_author_name 'Dr Tristram Chivers' _publ_contact_author_address ; Department of Chemistry University of Calgary Calgary Alberta T2N 1N4 Canada ; _publ_contact_author_email chivers@ucalgary.ca _publ_contact_author_fax '001 403 289 9488' _publ_contact_author_phone '001 403 220 5741' _publ_contact_letter ; To: Chemical Communications Please accept the following CIF data which is being submitted in support of an upcoming communication to be published in Chem. Commun. Please forward any questions concerning this CIF to Dr. Tristram Chivers (chivers@ucalgary.ca). ; _publ_requested_journal 'chem. Commun.' # TITLE AND AUTHOR LIST _publ_section_title ; Acyclic Imidoselenium(II) Dihalides: Synthesis and X-ray structures of ClSe[N(tBu)Se]nCl (n = 1,2) ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Chivers, Tristram' . ; Department of Chemistry University of Calgary Calgary, Alberta T2N 1N4 Canada ; 'T. Maaninen' . ; Department of Chemistry University of Oulu Oulu, FIN-90401 Finland ; 'Risto Laitinen' . ; Department of Chemistry University of Oulu Oulu, FIN-90401 Finland ; 'Elina Wegelius' . ; Department of Chemistry University of Jyvaeskylae Jyvaeskylae, 40351 Finland ; #================================================================= data_tim4ab _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H9 Cl2 N Se2' _chemical_formula_weight 299.94 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 monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.2630(10) _cell_length_b 10.2820(10) _cell_length_c 12.3120(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.060(10) _cell_angle_gamma 90.00 _cell_volume 918.84(17) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 8.553 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1835 _exptl_absorpt_correction_T_max 0.3602 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 4419 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2076 _reflns_number_gt 1797 _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^)+(0.0877P)^2^+5.8308P] 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 0.001(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2076 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1947 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _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 Se1 Se 0.20664(10) 0.55916(8) 0.87573(6) 0.0301(3) Uani 1 d . . . Se2 Se 0.21155(11) 0.56120(7) 0.62560(7) 0.0322(3) Uani 1 d . . . Cl1 Cl 0.0854(3) 0.3632(2) 0.89979(19) 0.0419(6) Uani 1 d . . . Cl2 Cl 0.1269(3) 0.3607(2) 0.58090(19) 0.0430(6) Uani 1 d . . . N1 N 0.3372(9) 0.5413(7) 0.7547(5) 0.0297(13) Uani 1 d . . . C1 C 0.5399(10) 0.4971(8) 0.7638(7) 0.0325(16) Uani 1 d . . . C2 C 0.6192(14) 0.4911(11) 0.6529(8) 0.051(2) Uani 1 d . . . H2A H 0.7435 0.4539 0.6586 0.077 Uiso 1 calc R . . H2B H 0.6253 0.5790 0.6225 0.077 Uiso 1 calc R . . H2C H 0.5407 0.4364 0.6053 0.077 Uiso 1 calc R . . C3 C 0.6438(12) 0.5963(10) 0.8333(9) 0.044(2) Uani 1 d . . . H3A H 0.5946 0.5971 0.9064 0.067 Uiso 1 calc R . . H3B H 0.6293 0.6827 0.8005 0.067 Uiso 1 calc R . . H3C H 0.7748 0.5732 0.8380 0.067 Uiso 1 calc R . . C4 C 0.5459(13) 0.3645(9) 0.8163(9) 0.043(2) Uani 1 d . . . H4A H 0.4776 0.3023 0.7700 0.065 Uiso 1 calc R . . H4B H 0.4897 0.3690 0.8874 0.065 Uiso 1 calc R . . H4C H 0.6742 0.3360 0.8257 0.065 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 0.0288(5) 0.0304(5) 0.0315(5) -0.0019(3) 0.0048(3) 0.0004(3) Se2 0.0383(5) 0.0276(5) 0.0305(5) 0.0006(3) -0.0010(3) 0.0013(3) Cl1 0.0394(10) 0.0374(11) 0.0495(12) -0.0010(9) 0.0091(9) -0.0068(8) Cl2 0.0516(12) 0.0327(11) 0.0441(12) -0.0020(8) -0.0059(9) -0.0035(9) N1 0.027(3) 0.039(4) 0.024(3) 0.000(2) 0.006(2) 0.004(3) C1 0.024(3) 0.033(4) 0.041(4) -0.001(3) 0.006(3) 0.003(3) C2 0.046(5) 0.066(7) 0.042(5) -0.002(5) 0.012(4) 0.004(5) C3 0.028(4) 0.041(5) 0.064(6) -0.002(4) -0.003(4) -0.005(4) C4 0.040(5) 0.033(5) 0.058(6) 0.001(4) 0.003(4) 0.006(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 N1 1.804(6) . ? Se1 Cl1 2.223(2) . ? Se2 N1 1.816(7) . ? Se2 Cl2 2.215(2) . ? N1 C1 1.541(10) . ? C1 C2 1.502(12) . ? C1 C4 1.509(12) . ? C1 C3 1.515(12) . ? 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 N1 Se1 Cl1 103.9(2) . . ? N1 Se2 Cl2 103.8(2) . . ? C1 N1 Se1 119.9(5) . . ? C1 N1 Se2 123.1(5) . . ? Se1 N1 Se2 116.7(4) . . ? C2 C1 C4 110.3(8) . . ? C2 C1 C3 110.0(8) . . ? C4 C1 C3 111.1(8) . . ? C2 C1 N1 110.0(7) . . ? C4 C1 N1 108.1(6) . . ? C3 C1 N1 107.3(7) . . ? 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 Cl1 Se1 N1 C1 -89.0(6) . . . . ? Cl1 Se1 N1 Se2 84.8(4) . . . . ? Cl2 Se2 N1 C1 80.8(6) . . . . ? Cl2 Se2 N1 Se1 -92.9(4) . . . . ? Se1 N1 C1 C2 -179.3(6) . . . . ? Se2 N1 C1 C2 7.3(10) . . . . ? Se1 N1 C1 C4 60.3(8) . . . . ? Se2 N1 C1 C4 -113.2(7) . . . . ? Se1 N1 C1 C3 -59.7(8) . . . . ? Se2 N1 C1 C3 126.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 2.690 _refine_diff_density_min -1.135 _refine_diff_density_rms 0.249 # ======================== END ====================== data_tim6ab _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 Cl2 N2 Se3' _chemical_formula_weight 450.02 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 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 9.989(2) _cell_length_b 9.643(2) _cell_length_c 16.124(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.81(3) _cell_angle_gamma 90.00 _cell_volume 1520.2(5) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.966 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 7.586 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3122 _exptl_absorpt_correction_T_max 0.5176 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 10567 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3121 _reflns_number_gt 2629 _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^)+(0.0901P)^2^+2.3036P] 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 0.0028(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3121 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 0.692 _refine_ls_restrained_S_all 0.692 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7076(3) 0.6072(4) 0.2710(2) 0.0260(7) Uani 1 d . . . C2 C 0.7237(4) 0.2352(4) 0.0646(2) 0.0263(7) Uani 1 d . . . C11 C 0.8300(4) 0.6483(5) 0.3388(2) 0.0386(9) Uani 1 d . . . H11A H 0.7989 0.6763 0.3902 0.058 Uiso 1 calc R . . H11B H 0.8776 0.7260 0.3184 0.058 Uiso 1 calc R . . H11C H 0.8924 0.5693 0.3516 0.058 Uiso 1 calc R . . C12 C 0.6283(5) 0.4915(4) 0.3048(3) 0.0404(10) Uani 1 d . . . H12A H 0.5450 0.4704 0.2629 0.061 Uiso 1 calc R . . H12B H 0.6035 0.5219 0.3577 0.061 Uiso 1 calc R . . H12C H 0.6855 0.4083 0.3155 0.061 Uiso 1 calc R . . C13 C 0.6165(4) 0.7313(4) 0.2441(2) 0.0372(9) Uani 1 d . . . H13A H 0.5894 0.7720 0.2938 0.056 Uiso 1 calc R . . H13B H 0.5347 0.7018 0.2033 0.056 Uiso 1 calc R . . H13C H 0.6663 0.8004 0.2176 0.056 Uiso 1 calc R . . C21 C 0.5821(4) 0.1730(5) 0.0322(3) 0.0455(10) Uani 1 d . . . H21A H 0.5853 0.0729 0.0427 0.068 Uiso 1 calc R . . H21B H 0.5538 0.1903 -0.0288 0.068 Uiso 1 calc R . . H21C H 0.5164 0.2160 0.0619 0.068 Uiso 1 calc R . . C22 C 0.7705(5) 0.2078(4) 0.1591(2) 0.0403(10) Uani 1 d . . . H22A H 0.7798 0.1076 0.1690 0.060 Uiso 1 calc R . . H22B H 0.7028 0.2451 0.1894 0.060 Uiso 1 calc R . . H22C H 0.8589 0.2529 0.1798 0.060 Uiso 1 calc R . . C23 C 0.8260(4) 0.1707(4) 0.0170(2) 0.0374(9) Uani 1 d . . . H23A H 0.8264 0.0698 0.0240 0.056 Uiso 1 calc R . . H23B H 0.9176 0.2074 0.0398 0.056 Uiso 1 calc R . . H23C H 0.7994 0.1937 -0.0434 0.056 Uiso 1 calc R . . N1 N 0.7552(3) 0.5487(3) 0.19461(17) 0.0229(6) Uani 1 d . . . N2 N 0.7101(3) 0.3885(3) 0.04657(16) 0.0225(6) Uani 1 d . . . Cl1 Cl 0.91688(13) 0.81066(12) 0.12768(8) 0.0548(3) Uani 1 d . . . Cl2 Cl 0.74688(10) 0.43773(11) -0.14110(5) 0.0364(2) Uani 1 d . . . Se1 Se 0.91591(3) 0.58735(4) 0.17195(2) 0.02799(13) Uani 1 d . . . Se2 Se 0.83198(3) 0.48714(4) 0.00018(2) 0.02574(13) Uani 1 d . . . Se3 Se 0.60797(3) 0.49623(4) 0.10078(2) 0.02449(13) Uani 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 C1 0.0264(17) 0.0277(19) 0.0245(16) -0.0022(14) 0.0069(13) 0.0005(15) C2 0.0339(19) 0.0215(18) 0.0233(15) 0.0016(13) 0.0058(13) -0.0029(14) C11 0.032(2) 0.048(3) 0.0332(19) -0.0152(18) 0.0012(15) 0.0010(18) C12 0.056(3) 0.039(2) 0.031(2) -0.0040(16) 0.0196(18) -0.0099(19) C13 0.036(2) 0.035(2) 0.041(2) -0.0060(17) 0.0080(16) 0.0089(18) C21 0.047(2) 0.035(2) 0.054(2) -0.004(2) 0.0083(19) -0.016(2) C22 0.064(3) 0.033(2) 0.0225(17) 0.0034(15) 0.0056(16) 0.007(2) C23 0.051(2) 0.030(2) 0.0322(18) 0.0013(16) 0.0093(16) 0.0081(18) N1 0.0222(14) 0.0244(15) 0.0223(13) -0.0021(11) 0.0050(10) 0.0000(12) N2 0.0195(13) 0.0272(16) 0.0215(13) -0.0017(11) 0.0061(10) -0.0023(11) Cl1 0.0671(7) 0.0314(6) 0.0732(7) -0.0011(5) 0.0317(6) -0.0132(5) Cl2 0.0407(5) 0.0475(6) 0.0217(4) 0.0034(4) 0.0081(3) 0.0033(4) Se1 0.0222(2) 0.0306(2) 0.0312(2) -0.00644(14) 0.00556(13) -0.00411(14) Se2 0.0239(2) 0.0276(2) 0.0270(2) 0.00302(13) 0.00815(14) -0.00329(14) Se3 0.0185(2) 0.0323(2) 0.0220(2) -0.00115(13) 0.00248(13) 0.00283(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 C1 C13 1.512(5) . ? C1 N1 1.516(4) . ? C1 C11 1.517(5) . ? C1 C12 1.532(5) . ? C2 N2 1.507(5) . ? C2 C22 1.524(5) . ? C2 C21 1.527(5) . ? C2 C23 1.530(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 Se1 1.758(3) . ? N1 Se3 1.948(3) . ? N2 Se3 1.803(3) . ? N2 Se2 1.822(3) . ? Cl1 Se1 2.2693(12) . ? Cl2 Se2 2.3121(9) . ? 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 C13 C1 N1 109.4(3) . . ? C13 C1 C11 110.4(3) . . ? N1 C1 C11 110.0(3) . . ? C13 C1 C12 110.7(3) . . ? N1 C1 C12 106.8(3) . . ? C11 C1 C12 109.4(3) . . ? N2 C2 C22 111.1(3) . . ? N2 C2 C21 106.2(3) . . ? C22 C2 C21 110.3(3) . . ? N2 C2 C23 110.2(3) . . ? C22 C2 C23 109.4(3) . . ? C21 C2 C23 109.6(3) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C13 H13A 109.5 . . ? C1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 N1 Se1 122.7(2) . . ? C1 N1 Se3 114.5(2) . . ? Se1 N1 Se3 118.03(14) . . ? C2 N2 Se3 120.6(2) . . ? C2 N2 Se2 123.4(2) . . ? Se3 N2 Se2 112.97(16) . . ? N1 Se1 Cl1 109.24(10) . . ? N2 Se2 Cl2 98.92(8) . . ? N2 Se3 N1 96.54(12) . . ? 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 C13 C1 N1 Se1 98.3(3) . . . . ? C11 C1 N1 Se1 -23.1(4) . . . . ? C12 C1 N1 Se1 -141.8(3) . . . . ? C13 C1 N1 Se3 -56.8(3) . . . . ? C11 C1 N1 Se3 -178.3(3) . . . . ? C12 C1 N1 Se3 63.0(3) . . . . ? C22 C2 N2 Se3 -53.3(4) . . . . ? C21 C2 N2 Se3 66.7(3) . . . . ? C23 C2 N2 Se3 -174.6(2) . . . . ? C22 C2 N2 Se2 105.6(3) . . . . ? C21 C2 N2 Se2 -134.4(3) . . . . ? C23 C2 N2 Se2 -15.8(4) . . . . ? C1 N1 Se1 Cl1 -71.4(3) . . . . ? Se3 N1 Se1 Cl1 82.99(16) . . . . ? C2 N2 Se2 Cl2 83.2(2) . . . . ? Se3 N2 Se2 Cl2 -116.47(12) . . . . ? C2 N2 Se3 N1 91.6(2) . . . . ? Se2 N2 Se3 N1 -69.36(15) . . . . ? C1 N1 Se3 N2 -162.8(2) . . . . ? Se1 N1 Se3 N2 40.82(19) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.566 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.095