# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Paul Ragogna' 'Jason L. Dutton' 'Michael C. Jennings' 'Jocelyn J. Tindale' _publ_contact_author_name 'Paul Ragogna' _publ_contact_author_address ; Department of Chemistry The University of Western Ontario The University of Western Ontario 1151 Richmond St. London Ontario N6A 5B7 CANADA ; _publ_contact_author_email PRAGOGNA@UWO.CA _publ_requested_journal 'Chemical Communications' _publ_section_title ; The Direct Reaction of the tBu-DAB Ligand with SeCl4: A Redox Route to Selenium-Nitrogen Heterocycles ; data_05139b _database_code_depnum_ccdc_archive 'CCDC 601829' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 Cl N2 Se' _chemical_formula_weight 225.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -.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 9.1855(7) _cell_length_b 9.2467(7) _cell_length_c 10.3396(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.012(4) _cell_angle_gamma 90.00 _cell_volume 852.07(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2553 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4210 _exptl_absorpt_correction_T_max 0.6054 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10131 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2110 _reflns_number_gt 1669 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0347P)^2^+0.0079P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2110 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0682 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.01109(3) 0.03708(3) 0.27627(3) 0.02001(10) Uani 1 1 d . . . Cl1 Cl -0.21503(8) -0.00519(8) 0.38277(7) 0.02454(17) Uani 1 1 d . . . N1 N -0.1177(3) 0.1280(3) 0.1408(2) 0.0219(5) Uani 1 1 d . . . C1 C -0.0495(3) 0.1800(3) 0.0542(2) 0.0229(6) Uani 1 1 d . . . H2A H -0.1035 0.2321 -0.0215 0.027 Uiso 1 1 calc R . . C2 C 0.1072(3) 0.1571(3) 0.0754(2) 0.0210(6) Uani 1 1 d . . . H3A H 0.1641 0.1914 0.0163 0.025 Uiso 1 1 calc R . . N2 N 0.1653(2) 0.0849(3) 0.1830(2) 0.0183(5) Uani 1 1 d . . . C5 C 0.3295(3) 0.0530(3) 0.2372(3) 0.0196(6) Uani 1 1 d . . . C6 C 0.3887(3) 0.1671(3) 0.3430(2) 0.0252(7) Uani 1 1 d . . . H6A H 0.3351 0.1598 0.4140 0.038 Uiso 1 1 calc R . . H6B H 0.3729 0.2635 0.3026 0.038 Uiso 1 1 calc R . . H6C H 0.4962 0.1516 0.3806 0.038 Uiso 1 1 calc R . . C7 C 0.4110(3) 0.0604(3) 0.1255(3) 0.0257(7) Uani 1 1 d . . . H7A H 0.3710 -0.0139 0.0588 0.038 Uiso 1 1 calc R . . H7B H 0.5184 0.0437 0.1622 0.038 Uiso 1 1 calc R . . H7C H 0.3960 0.1561 0.0837 0.038 Uiso 1 1 calc R . . C8 C 0.3442(3) -0.0971(3) 0.2995(3) 0.0241(6) Uani 1 1 d . . . H8A H 0.3060 -0.1693 0.2302 0.036 Uiso 1 1 calc R . . H8B H 0.2862 -0.1015 0.3673 0.036 Uiso 1 1 calc R . . H8C H 0.4501 -0.1170 0.3409 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.01736(16) 0.02342(18) 0.01958(16) 0.00156(11) 0.00512(11) 0.00178(12) Cl1 0.0194(4) 0.0297(4) 0.0258(4) -0.0005(3) 0.0079(3) -0.0012(3) N1 0.0224(13) 0.0212(14) 0.0212(11) -0.0025(10) 0.0034(10) 0.0023(10) C1 0.0258(16) 0.0206(16) 0.0201(14) 0.0009(12) 0.0013(12) 0.0037(13) C2 0.0265(16) 0.0186(15) 0.0182(13) -0.0005(11) 0.0058(12) -0.0009(13) N2 0.0182(12) 0.0192(13) 0.0179(11) -0.0005(10) 0.0053(9) 0.0005(10) C5 0.0151(14) 0.0244(17) 0.0202(14) -0.0002(11) 0.0062(11) 0.0013(12) C6 0.0218(16) 0.0304(18) 0.0238(14) -0.0015(13) 0.0065(12) -0.0028(13) C7 0.0212(16) 0.036(2) 0.0210(14) 0.0004(12) 0.0080(12) 0.0005(13) C8 0.0211(15) 0.0258(17) 0.0261(15) 0.0015(13) 0.0072(12) 0.0022(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 Se1 N1 1.807(2) . ? Se1 N2 1.948(2) . ? Se1 Cl1 2.6051(8) . ? N1 C1 1.303(3) . ? C1 C2 1.418(4) . ? C1 H2A 0.9500 . ? C2 N2 1.297(3) . ? C2 H3A 0.9500 . ? N2 C5 1.505(3) . ? C5 C8 1.522(4) . ? C5 C7 1.522(4) . ? C5 C6 1.523(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Se1 N2 85.91(10) . . ? N1 Se1 Cl1 87.60(8) . . ? N2 Se1 Cl1 173.31(7) . . ? C1 N1 Se1 111.8(2) . . ? N1 C1 C2 118.5(2) . . ? N1 C1 H2A 120.7 . . ? C2 C1 H2A 120.7 . . ? N2 C2 C1 113.7(2) . . ? N2 C2 H3A 123.2 . . ? C1 C2 H3A 123.2 . . ? C2 N2 C5 126.0(2) . . ? C2 N2 Se1 110.10(19) . . ? C5 N2 Se1 123.64(16) . . ? N2 C5 C8 108.4(2) . . ? N2 C5 C7 109.9(2) . . ? C8 C5 C7 110.6(2) . . ? N2 C5 C6 106.4(2) . . ? C8 C5 C6 110.4(2) . . ? C7 C5 C6 111.0(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Se1 N1 C1 -1.1(2) . . . . ? Cl1 Se1 N1 C1 177.23(19) . . . . ? Se1 N1 C1 C2 1.1(3) . . . . ? N1 C1 C2 N2 -0.3(4) . . . . ? C1 C2 N2 C5 -175.3(2) . . . . ? C1 C2 N2 Se1 -0.6(3) . . . . ? N1 Se1 N2 C2 1.00(19) . . . . ? Cl1 Se1 N2 C2 -13.1(7) . . . . ? N1 Se1 N2 C5 175.9(2) . . . . ? Cl1 Se1 N2 C5 161.8(5) . . . . ? C2 N2 C5 C8 -144.3(3) . . . . ? Se1 N2 C5 C8 41.7(3) . . . . ? C2 N2 C5 C7 -23.3(4) . . . . ? Se1 N2 C5 C7 162.70(19) . . . . ? C2 N2 C5 C6 97.0(3) . . . . ? Se1 N2 C5 C6 -77.0(2) . . . . ? _diffrn_measured_fraction_theta_max .998 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full .998 _refine_diff_density_max .462 _refine_diff_density_min -.631 _refine_diff_density_rms .108 data_05152 _database_code_depnum_ccdc_archive 'CCDC 601830' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H25 Cl6 N5 Se3' _chemical_formula_weight 712.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -.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 14.5099(4) _cell_length_b 10.4455(2) _cell_length_c 16.7518(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.718(2) _cell_angle_gamma 90.00 _cell_volume 2533.61(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5750 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 5.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2557 _exptl_absorpt_correction_T_max 0.3401 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25379 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4477 _reflns_number_gt 3662 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0001P)^2^+34.6784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4477 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.08020(14) 0.2260(2) 0.13779(17) 0.0384(6) Uani 1 1 d . . . Se1 Se -0.02995(6) 0.51097(8) -0.12252(6) 0.0253(2) Uani 1 1 d . . . N1 N 0.0847(5) 0.5722(7) -0.1118(4) 0.0250(16) Uani 1 1 d . . . C1 C 0.1437(6) 0.4801(9) -0.1002(6) 0.029(2) Uani 1 1 d . . . H13A H 0.2080 0.4971 -0.0929 0.035 Uiso 1 1 calc R . . Se2 Se 0.25342(5) 0.22838(7) 0.15457(5) 0.0186(2) Uani 1 1 d . . . Cl2 Cl 0.41208(13) 0.2305(2) 0.16929(13) 0.0251(5) Uani 1 1 d . . . C2 C 0.1099(5) 0.3546(8) -0.0986(5) 0.026(2) Uani 1 1 d . . . H14A H 0.1486 0.2821 -0.0890 0.031 Uiso 1 1 calc R . . N2 N 0.0216(4) 0.3463(6) -0.1112(4) 0.0220(15) Uani 1 1 d . . . Cl3 Cl 0.25819(15) 0.4426(2) 0.07984(15) 0.0307(5) Uani 1 1 d . . . Se3 Se 0.59588(6) 0.62908(8) 0.02289(5) 0.0220(2) Uani 1 1 d . . . N3 N 0.6202(5) 0.4917(7) 0.0820(4) 0.0235(16) Uani 1 1 d . . . C3 C 0.5664(6) 0.4865(8) 0.1422(5) 0.0248(19) Uani 1 1 d . . . H23A H 0.5705 0.4185 0.1798 0.030 Uiso 1 1 calc R . . Cl4 Cl 0.26101(15) 0.1142(2) 0.02726(13) 0.0286(5) Uani 1 1 d . . . C4 C 0.5021(6) 0.5875(8) 0.1479(5) 0.0228(19) Uani 1 1 d . . . H24A H 0.4611 0.5938 0.1898 0.027 Uiso 1 1 calc R . . N4 N 0.5044(4) 0.6707(6) 0.0905(4) 0.0200(15) Uani 1 1 d . . . Cl5 Cl 0.24937(15) 0.0387(2) 0.22035(14) 0.0316(5) Uani 1 1 d . . . Cl6 Cl 0.24738(18) 0.3389(2) 0.27559(15) 0.0420(6) Uani 1 1 d . . . C16 C -0.0370(6) 0.2264(8) -0.1183(6) 0.026(2) Uani 1 1 d . . . C17 C -0.0989(8) 0.2439(11) -0.1959(7) 0.057(3) Uani 1 1 d . . . H17A H -0.1382 0.3194 -0.1908 0.086 Uiso 1 1 calc R . . H17B H -0.1378 0.1679 -0.2050 0.086 Uiso 1 1 calc R . . H17C H -0.0601 0.2555 -0.2411 0.086 Uiso 1 1 calc R . . C18 C 0.0243(8) 0.1126(10) -0.1224(9) 0.062(4) Uani 1 1 d . . . H18A H 0.0621 0.1043 -0.0720 0.093 Uiso 1 1 calc R . . H18B H 0.0647 0.1230 -0.1666 0.093 Uiso 1 1 calc R . . H18C H -0.0134 0.0354 -0.1312 0.093 Uiso 1 1 calc R . . C19 C -0.0957(7) 0.2221(10) -0.0488(7) 0.042(3) Uani 1 1 d . . . H19A H -0.0565 0.2100 0.0005 0.064 Uiso 1 1 calc R . . H19B H -0.1394 0.1508 -0.0555 0.064 Uiso 1 1 calc R . . H19C H -0.1298 0.3027 -0.0457 0.064 Uiso 1 1 calc R . . C26 C 0.4473(6) 0.7929(8) 0.0816(5) 0.0244(19) Uani 1 1 d . . . C27 C 0.4554(7) 0.8403(9) -0.0039(6) 0.034(2) Uani 1 1 d . . . H27A H 0.4198 0.9195 -0.0121 0.052 Uiso 1 1 calc R . . H27B H 0.4312 0.7750 -0.0417 0.052 Uiso 1 1 calc R . . H27C H 0.5204 0.8569 -0.0128 0.052 Uiso 1 1 calc R . . C28 C 0.4901(7) 0.8868(9) 0.1419(6) 0.038(2) Uani 1 1 d . . . H28A H 0.4558 0.9676 0.1384 0.057 Uiso 1 1 calc R . . H28B H 0.5546 0.9024 0.1305 0.057 Uiso 1 1 calc R . . H28C H 0.4878 0.8513 0.1959 0.057 Uiso 1 1 calc R . . C29 C 0.3475(6) 0.7618(10) 0.0936(7) 0.045(3) Uani 1 1 d . . . H29A H 0.3104 0.8400 0.0881 0.067 Uiso 1 1 calc R . . H29B H 0.3426 0.7259 0.1472 0.067 Uiso 1 1 calc R . . H29C H 0.3249 0.6992 0.0534 0.067 Uiso 1 1 calc R . . N31 N 0.3559(6) 0.8126(10) -0.2038(6) 0.054(3) Uani 1 1 d . . . C32 C 0.2929(7) 0.8341(9) -0.1685(6) 0.033(2) Uani 1 1 d . . . C33 C 0.2127(7) 0.8605(10) -0.1241(6) 0.042(3) Uani 1 1 d . . . H33A H 0.1747 0.9260 -0.1522 0.064 Uiso 1 1 calc R . . H33B H 0.2327 0.8915 -0.0706 0.064 Uiso 1 1 calc R . . H33C H 0.1765 0.7820 -0.1196 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0171(10) 0.0256(11) 0.0725(19) 0.0037(12) 0.0019(11) 0.0009(9) Se1 0.0146(4) 0.0258(5) 0.0351(5) -0.0001(4) -0.0003(4) 0.0012(3) N1 0.018(4) 0.029(4) 0.028(4) -0.001(3) 0.002(3) -0.002(3) C1 0.016(4) 0.034(5) 0.038(6) -0.002(4) -0.001(4) 0.000(4) Se2 0.0165(4) 0.0174(4) 0.0224(5) -0.0020(3) 0.0046(3) -0.0006(3) Cl2 0.0159(9) 0.0330(11) 0.0263(12) -0.0005(9) 0.0011(8) -0.0025(8) C2 0.015(4) 0.027(5) 0.036(5) -0.003(4) 0.000(4) 0.006(3) N2 0.018(4) 0.025(4) 0.023(4) -0.005(3) 0.003(3) 0.000(3) Cl3 0.0288(11) 0.0212(11) 0.0436(14) 0.0040(10) 0.0146(10) 0.0050(9) Se3 0.0196(4) 0.0240(4) 0.0230(5) 0.0036(4) 0.0065(3) 0.0033(3) N3 0.020(4) 0.027(4) 0.023(4) -0.001(3) -0.001(3) 0.000(3) C3 0.026(4) 0.028(5) 0.021(5) 0.005(4) 0.004(4) 0.000(4) Cl4 0.0362(12) 0.0245(11) 0.0248(12) -0.0078(9) -0.0012(9) 0.0008(9) C4 0.025(4) 0.027(5) 0.017(5) 0.002(4) 0.000(4) -0.001(4) N4 0.018(3) 0.019(3) 0.023(4) -0.003(3) 0.003(3) 0.000(3) Cl5 0.0325(12) 0.0270(11) 0.0353(14) 0.0112(10) 0.0035(10) -0.0019(9) Cl6 0.0483(15) 0.0455(15) 0.0345(14) -0.0195(11) 0.0211(12) -0.0120(11) C16 0.024(4) 0.024(4) 0.032(5) -0.002(4) 0.009(4) -0.006(4) C17 0.076(8) 0.055(7) 0.039(7) -0.005(6) -0.008(6) -0.038(6) C18 0.050(7) 0.024(6) 0.116(12) -0.009(6) 0.027(7) -0.001(5) C19 0.036(6) 0.037(6) 0.056(7) -0.004(5) 0.020(5) -0.013(5) C26 0.025(4) 0.016(4) 0.032(5) 0.005(4) 0.006(4) 0.005(3) C27 0.044(6) 0.027(5) 0.034(6) 0.008(4) 0.014(5) 0.011(4) C28 0.051(6) 0.029(5) 0.033(6) 0.000(4) -0.007(5) 0.010(5) C29 0.027(5) 0.036(6) 0.071(8) 0.011(5) 0.004(5) 0.010(4) N31 0.046(6) 0.074(7) 0.043(6) -0.003(5) 0.006(5) 0.021(5) C32 0.043(6) 0.031(5) 0.025(5) -0.001(4) -0.004(5) 0.006(4) C33 0.050(6) 0.043(6) 0.036(6) -0.005(5) 0.020(5) -0.011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 Se2 2.511(2) . ? Se1 N1 1.780(7) . ? Se1 N2 1.880(7) . ? N1 C1 1.295(11) . ? C1 C2 1.400(12) . ? Se2 Cl5 2.270(2) . ? Se2 Cl2 2.299(2) . ? Se2 Cl6 2.340(2) . ? Se2 Cl4 2.453(2) . ? Se2 Cl3 2.567(2) . ? C2 N2 1.289(10) . ? N2 C16 1.514(10) . ? Se3 N3 1.766(7) . ? Se3 N4 1.852(7) . ? N3 C3 1.315(11) . ? C3 C4 1.416(12) . ? C4 N4 1.298(10) . ? N4 C26 1.524(10) . ? C16 C19 1.487(12) . ? C16 C18 1.489(13) . ? C16 C17 1.542(14) . ? C26 C29 1.510(12) . ? C26 C28 1.512(12) . ? C26 C27 1.527(12) . ? N31 C32 1.144(12) . ? C32 C33 1.447(13) . ? 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 N2 87.5(3) . . ? C1 N1 Se1 110.7(6) . . ? N1 C1 C2 118.0(7) . . ? Cl5 Se2 Cl2 90.78(8) . . ? Cl5 Se2 Cl6 90.37(10) . . ? Cl2 Se2 Cl6 89.76(9) . . ? Cl5 Se2 Cl4 90.09(8) . . ? Cl2 Se2 Cl4 89.82(8) . . ? Cl6 Se2 Cl4 179.38(9) . . ? Cl5 Se2 Cl1 89.33(8) . . ? Cl2 Se2 Cl1 179.73(10) . . ? Cl6 Se2 Cl1 90.48(9) . . ? Cl4 Se2 Cl1 89.93(9) . . ? Cl5 Se2 Cl3 179.85(10) . . ? Cl2 Se2 Cl3 89.17(8) . . ? Cl6 Se2 Cl3 89.77(9) . . ? Cl4 Se2 Cl3 89.76(8) . . ? Cl1 Se2 Cl3 90.72(8) . . ? N2 C2 C1 113.9(7) . . ? C2 N2 C16 128.0(7) . . ? C2 N2 Se1 109.9(6) . . ? C16 N2 Se1 122.1(5) . . ? N3 Se3 N4 88.4(3) . . ? C3 N3 Se3 110.9(6) . . ? N3 C3 C4 116.7(8) . . ? N4 C4 C3 113.5(8) . . ? C4 N4 C26 126.4(7) . . ? C4 N4 Se3 110.5(6) . . ? C26 N4 Se3 122.9(5) . . ? C19 C16 C18 112.7(9) . . ? C19 C16 N2 108.0(7) . . ? C18 C16 N2 109.3(7) . . ? C19 C16 C17 109.3(8) . . ? C18 C16 C17 111.9(9) . . ? N2 C16 C17 105.2(7) . . ? C29 C26 C28 114.0(8) . . ? C29 C26 N4 109.0(7) . . ? C28 C26 N4 106.3(7) . . ? C29 C26 C27 109.1(8) . . ? C28 C26 C27 111.3(8) . . ? N4 C26 C27 106.8(7) . . ? N31 C32 C33 179.6(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 N2 Se1 N1 C1 -1.6(7) . . . . ? Se1 N1 C1 C2 0.5(11) . . . . ? N1 C1 C2 N2 1.5(13) . . . . ? C1 C2 N2 C16 176.1(8) . . . . ? C1 C2 N2 Se1 -2.6(10) . . . . ? N1 Se1 N2 C2 2.4(6) . . . . ? N1 Se1 N2 C16 -176.4(7) . . . . ? N4 Se3 N3 C3 -1.0(6) . . . . ? Se3 N3 C3 C4 0.0(9) . . . . ? N3 C3 C4 N4 1.5(11) . . . . ? C3 C4 N4 C26 -177.0(7) . . . . ? C3 C4 N4 Se3 -2.2(9) . . . . ? N3 Se3 N4 C4 1.8(6) . . . . ? N3 Se3 N4 C26 176.9(6) . . . . ? C2 N2 C16 C19 113.4(10) . . . . ? Se1 N2 C16 C19 -68.0(9) . . . . ? C2 N2 C16 C18 -9.6(13) . . . . ? Se1 N2 C16 C18 169.1(8) . . . . ? C2 N2 C16 C17 -129.9(10) . . . . ? Se1 N2 C16 C17 48.7(9) . . . . ? C4 N4 C26 C29 -48.2(11) . . . . ? Se3 N4 C26 C29 137.6(7) . . . . ? C4 N4 C26 C28 75.1(10) . . . . ? Se3 N4 C26 C28 -99.2(8) . . . . ? C4 N4 C26 C27 -166.0(8) . . . . ? Se3 N4 C26 C27 19.8(9) . . . . ? _diffrn_measured_fraction_theta_max .998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full .998 _refine_diff_density_max .915 _refine_diff_density_min -.724 _refine_diff_density_rms .153 data_06038b _database_code_depnum_ccdc_archive 'CCDC 601831' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 Cl4 Ga N2 Se' _chemical_formula_weight 401.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga .2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -.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 12.7117(5) _cell_length_b 9.9671(4) _cell_length_c 11.0754(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.724(2) _cell_angle_gamma 90.00 _cell_volume 1383.08(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3224 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 5.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1652 _exptl_absorpt_correction_T_max 0.4136 _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13055 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3174 _reflns_number_gt 2460 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 1997-2001)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0543P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0100(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3174 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.78257(3) -0.44030(4) 0.33543(4) 0.02608(15) Uani 1 1 d . . . Cl2 Cl 0.91115(9) -0.33558(11) 0.44878(10) 0.0464(3) Uani 1 1 d . . . Cl3 Cl 0.72034(9) -0.32602(10) 0.17208(8) 0.0415(3) Uani 1 1 d . . . Cl4 Cl 0.65174(8) -0.47600(11) 0.43524(9) 0.0371(3) Uani 1 1 d . . . Cl5 Cl 0.84005(7) -0.63244(9) 0.27882(8) 0.0303(2) Uani 1 1 d . . . Se1 Se 0.86264(3) 0.04202(4) 0.47759(3) 0.02198(13) Uani 1 1 d . . . N1 N 0.9548(2) -0.0043(3) 0.3797(3) 0.0250(7) Uani 1 1 d . . . C1 C 0.9079(3) -0.0174(4) 0.2665(3) 0.0267(8) Uani 1 1 d . . . H13A H 0.9463 -0.0429 0.2036 0.032 Uiso 1 1 calc R . . C2 C 0.7965(3) 0.0084(4) 0.2416(3) 0.0248(8) Uani 1 1 d . . . H14A H 0.7546 0.0019 0.1622 0.030 Uiso 1 1 calc R . . N2 N 0.7573(2) 0.0422(3) 0.3400(3) 0.0191(6) Uani 1 1 d . . . C16 C 0.6414(3) 0.0702(3) 0.3425(3) 0.0214(8) Uani 1 1 d . . . C17 C 0.5979(3) 0.1577(4) 0.2349(3) 0.0278(8) Uani 1 1 d . . . H17A H 0.6029 0.1102 0.1587 0.042 Uiso 1 1 calc R . . H17B H 0.6394 0.2409 0.2387 0.042 Uiso 1 1 calc R . . H17C H 0.5230 0.1790 0.2374 0.042 Uiso 1 1 calc R . . C18 C 0.6347(3) 0.1407(4) 0.4623(3) 0.0300(9) Uani 1 1 d . . . H18A H 0.6634 0.0820 0.5309 0.045 Uiso 1 1 calc R . . H18B H 0.5599 0.1617 0.4659 0.045 Uiso 1 1 calc R . . H18C H 0.6762 0.2240 0.4674 0.045 Uiso 1 1 calc R . . C19 C 0.5857(3) -0.0644(4) 0.3346(4) 0.0325(9) Uani 1 1 d . . . H19A H 0.5910 -0.1070 0.2561 0.049 Uiso 1 1 calc R . . H19B H 0.5103 -0.0515 0.3407 0.049 Uiso 1 1 calc R . . H19C H 0.6195 -0.1219 0.4018 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0287(3) 0.0268(2) 0.0230(2) 0.00053(16) 0.00516(19) -0.00056(17) Cl2 0.0478(7) 0.0409(6) 0.0476(6) -0.0092(5) -0.0001(5) -0.0149(5) Cl3 0.0643(8) 0.0350(6) 0.0264(5) 0.0061(4) 0.0113(5) 0.0137(5) Cl4 0.0284(5) 0.0569(7) 0.0267(5) 0.0049(5) 0.0072(4) 0.0027(5) Cl5 0.0275(5) 0.0260(5) 0.0382(5) 0.0005(4) 0.0079(4) -0.0012(4) Se1 0.0176(2) 0.0307(2) 0.0179(2) 0.00051(14) 0.00365(14) 0.00133(14) N1 0.0189(16) 0.0324(17) 0.0239(16) -0.0004(14) 0.0045(13) 0.0028(13) C1 0.0204(19) 0.037(2) 0.0228(19) -0.0005(16) 0.0040(16) -0.0016(16) C2 0.027(2) 0.0315(19) 0.0163(17) -0.0020(15) 0.0055(15) 0.0006(16) N2 0.0157(15) 0.0208(15) 0.0210(15) 0.0007(12) 0.0033(12) 0.0000(11) C16 0.0109(17) 0.0303(19) 0.0226(18) 0.0013(14) 0.0012(14) -0.0001(14) C17 0.0196(19) 0.032(2) 0.031(2) 0.0036(17) 0.0033(16) 0.0034(16) C18 0.024(2) 0.044(2) 0.0224(19) -0.0027(17) 0.0041(16) 0.0085(17) C19 0.025(2) 0.027(2) 0.046(3) 0.0001(18) 0.0073(19) -0.0035(16) _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 Ga1 Cl2 2.1549(11) . ? Ga1 Cl3 2.1708(11) . ? Ga1 Cl4 2.1762(10) . ? Ga1 Cl5 2.1793(10) . ? Se1 N1 1.787(3) . ? Se1 N2 1.851(3) . ? N1 C1 1.301(4) . ? C1 C2 1.420(5) . ? C1 H13A 0.9500 . ? C2 N2 1.317(4) . ? C2 H14A 0.9500 . ? N2 C16 1.504(4) . ? C16 C17 1.504(5) . ? C16 C19 1.513(5) . ? C16 C18 1.517(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Ga1 Cl3 111.42(5) . . ? Cl2 Ga1 Cl4 110.66(4) . . ? Cl3 Ga1 Cl4 107.88(4) . . ? Cl2 Ga1 Cl5 109.58(4) . . ? Cl3 Ga1 Cl5 108.30(4) . . ? Cl4 Ga1 Cl5 108.94(4) . . ? N1 Se1 N2 87.59(13) . . ? C1 N1 Se1 111.7(2) . . ? N1 C1 C2 116.7(3) . . ? N1 C1 H13A 121.7 . . ? C2 C1 H13A 121.7 . . ? N2 C2 C1 113.0(3) . . ? N2 C2 H14A 123.5 . . ? C1 C2 H14A 123.5 . . ? C2 N2 C16 124.8(3) . . ? C2 N2 Se1 111.1(2) . . ? C16 N2 Se1 124.1(2) . . ? C17 C16 N2 108.9(3) . . ? C17 C16 C19 111.2(3) . . ? N2 C16 C19 106.6(3) . . ? C17 C16 C18 110.9(3) . . ? N2 C16 C18 107.6(3) . . ? C19 C16 C18 111.5(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Se1 N1 C1 -1.0(3) . . . . ? Se1 N1 C1 C2 0.8(4) . . . . ? N1 C1 C2 N2 -0.1(5) . . . . ? C1 C2 N2 C16 -177.6(3) . . . . ? C1 C2 N2 Se1 -0.7(4) . . . . ? N1 Se1 N2 C2 1.0(2) . . . . ? N1 Se1 N2 C16 177.9(3) . . . . ? C2 N2 C16 C17 -44.7(4) . . . . ? Se1 N2 C16 C17 138.8(2) . . . . ? C2 N2 C16 C19 75.4(4) . . . . ? Se1 N2 C16 C19 -101.2(3) . . . . ? C2 N2 C16 C18 -165.0(3) . . . . ? Se1 N2 C16 C18 18.5(4) . . . . ? _diffrn_measured_fraction_theta_max .993 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full .993 _refine_diff_density_max .816 _refine_diff_density_min -.883 _refine_diff_density_rms .126