#------------------------------------------------------------------------------ #$Date: 2014-07-15 22:48:18 +0300 (Tue, 15 Jul 2014) $ #$Revision: 120443 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/18/7151831.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151831 loop_ _publ_author_name 'Mitamura, Takenori' 'Iwata, Kimiyo' 'Nomoto, Akihiro' 'Ogawa, Akiya' _publ_section_title ; Photochemical intramolecular cyclization of o-alkynylaryl isocyanides with organic dichalcogenides leading to 2,4-bischalcogenated quinolines. ; _journal_issue 10 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3768 _journal_page_last 3775 _journal_volume 9 _journal_year 2011 _chemical_formula_moiety 'C27 H17 Cl2 N Se2 ' _chemical_formula_sum 'C27 H17 Cl2 N Se2' _chemical_formula_weight 584.26 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_date 2009-12-02 _audit_creation_method 'by CrystalStructure 3.8' _cell_angle_alpha 74.4693(12) _cell_angle_beta 86.7204(13) _cell_angle_gamma 73.3481(13) _cell_formula_units_Z 2 _cell_length_a 6.0736(3) _cell_length_b 11.6934(5) _cell_length_c 17.7490(9) _cell_measurement_reflns_used 6469 _cell_measurement_temperature 103.1 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.4 _cell_volume 1163.33(10) _computing_cell_refinement PROCESS-AUTO _computing_data_collection PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_publication_material 'CrystalStructure 3.8' _computing_structure_refinement CRYSTALS _computing_structure_solution 'DIRDIF99 (PATTY)' _diffrn_ambient_temperature 103.1 _diffrn_detector_area_resol_mean 10.00 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11242 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _exptl_absorpt_coefficient_mu 3.424 _exptl_absorpt_correction_T_max 0.504 _exptl_absorpt_correction_T_min 0.254 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 576.00 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 3.16 _refine_diff_density_min -1.30 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 306 _refine_ls_number_reflns 4707 _refine_ls_R_factor_gt 0.0582 _refine_ls_shift/su_max 0.0000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[0.0069Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1941 _reflns_number_gt 4530 _reflns_number_total 5263 _reflns_threshold_expression F^2^>2.0\s(F^2^) _[local]_cod_data_source_file c0ob01168a.txt _[local]_cod_data_source_block '_SE' _[local]_cod_chemical_formula_sum_orig 'C27 H17 Cl2 N Se2 ' _cod_database_code 7151831 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z 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 Se(1) Se 0.29826(8) 0.98227(4) 0.11951(3) 0.02241(14) Uani 1.00 1 d . . . Se(2) Se 0.65948(7) 0.52981(4) 0.35290(2) 0.01909(14) Uani 1.00 1 d . . . Cl(1) Cl -0.6574(2) 1.40025(11) 0.11201(8) 0.0311(3) Uani 1.00 1 d . . . Cl(2) Cl 0.2451(2) 0.07514(10) 0.37062(8) 0.0322(3) Uani 1.00 1 d . . . N(1) N 0.0757(6) 0.9039(3) 0.2565(2) 0.0189(9) Uani 1.00 1 d . . . C(1) C 0.2610(7) 0.8688(3) 0.2179(2) 0.0185(10) Uani 1.00 1 d . . . C(2) C 0.0470(7) 0.8234(3) 0.3263(2) 0.0179(10) Uani 1.00 1 d . . . C(3) C -0.1650(8) 0.8576(4) 0.3639(2) 0.0247(12) Uani 1.00 1 d . . . C(4) C -0.2054(9) 0.7807(4) 0.4339(3) 0.0293(13) Uani 1.00 1 d . . . C(5) C -0.0367(8) 0.6693(4) 0.4677(2) 0.0228(11) Uani 1.00 1 d . . . C(6) C 0.1651(7) 0.6340(3) 0.4307(2) 0.0200(10) Uani 1.00 1 d . . . C(7) C 0.2134(7) 0.7084(3) 0.3584(2) 0.0158(10) Uani 1.00 1 d . . . C(8) C 0.4099(6) 0.6758(3) 0.3120(2) 0.0150(9) Uani 1.00 1 d . . . C(9) C 0.4364(7) 0.7526(3) 0.2410(2) 0.0155(10) Uani 1.00 1 d . . . C(10) C 0.6181(7) 0.7190(3) 0.1845(2) 0.0176(10) Uani 1.00 1 d . . . C(11) C 0.6129(8) 0.6277(3) 0.1479(2) 0.0237(11) Uani 1.00 1 d . . . C(12) C 0.7724(9) 0.6005(4) 0.0912(3) 0.0287(12) Uani 1.00 1 d . . . C(13) C 0.9376(8) 0.6641(4) 0.0706(2) 0.0264(12) Uani 1.00 1 d . . . C(14) C 0.9408(8) 0.7527(4) 0.1066(3) 0.0260(12) Uani 1.00 1 d . . . C(15) C 0.7823(7) 0.7813(4) 0.1633(2) 0.0213(11) Uani 1.00 1 d . . . C(16) C 0.0137(7) 1.1050(3) 0.1201(2) 0.0204(10) Uani 1.00 1 d . . . C(17) C -0.0152(8) 1.1877(4) 0.1647(3) 0.0290(13) Uani 1.00 1 d . . . C(18) C -0.2169(9) 1.2765(4) 0.1646(3) 0.0334(14) Uani 1.00 1 d . . . C(19) C -0.4000(8) 1.2856(4) 0.1148(2) 0.0228(11) Uani 1.00 1 d . . . C(20) C -0.3731(8) 1.2046(4) 0.0694(2) 0.0230(11) Uani 1.00 1 d . . . C(21) C -0.1705(7) 1.1133(3) 0.0713(2) 0.0214(11) Uani 1.00 1 d . . . C(22) C 0.5193(7) 0.4004(3) 0.3545(2) 0.0171(10) Uani 1.00 1 d . . . C(23) C 0.6485(8) 0.2807(3) 0.3960(2) 0.0216(11) Uani 1.00 1 d . . . C(24) C 0.5623(8) 0.1807(3) 0.3982(2) 0.0229(11) Uani 1.00 1 d . . . C(25) C 0.3585(8) 0.1990(4) 0.3645(2) 0.0223(11) Uani 1.00 1 d . . . C(26) C 0.2256(8) 0.3188(4) 0.3218(2) 0.0207(11) Uani 1.00 1 d . . . C(27) C 0.3155(8) 0.4179(3) 0.3191(2) 0.0226(11) Uani 1.00 1 d . . . H(1) H -0.2793 0.9335 0.3409 0.029 Uiso 1.00 1 c R . . H(2) H -0.3635 0.8053 0.4623 0.035 Uiso 1.00 1 c R . . H(3) H -0.0669 0.6125 0.5224 0.029 Uiso 1.00 1 c R . . H(4) H 0.2750 0.5580 0.4541 0.024 Uiso 1.00 1 c R . . H(5) H 0.4978 0.5832 0.1620 0.027 Uiso 1.00 1 c R . . H(6) H 0.7683 0.5350 0.0653 0.033 Uiso 1.00 1 c R . . H(7) H 1.0594 0.6437 0.0274 0.028 Uiso 1.00 1 c R . . H(8) H 1.0669 0.8011 0.0910 0.029 Uiso 1.00 1 c R . . H(9) H 0.7875 0.8439 0.1875 0.026 Uiso 1.00 1 c R . . H(10) H 0.1187 1.1824 0.1988 0.034 Uiso 1.00 1 c R . . H(11) H -0.2361 1.3340 0.1988 0.040 Uiso 1.00 1 c R . . H(12) H -0.5105 1.2125 0.0324 0.027 Uiso 1.00 1 c R . . H(13) H -0.1520 1.0499 0.0368 0.024 Uiso 1.00 1 c R . . H(14) H 0.7897 0.2684 0.4216 0.024 Uiso 1.00 1 c R . . H(15) H 0.6591 0.0897 0.4269 0.026 Uiso 1.00 1 c R . . H(16) H 0.0824 0.3309 0.2962 0.025 Uiso 1.00 1 c R . . H(17) H 0.2254 0.5052 0.2898 0.026 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Se(1) 0.0178(3) 0.0197(2) 0.0219(3) -0.00268(19) 0.00363(19) 0.00413(19) Se(2) 0.0135(2) 0.0166(2) 0.0227(3) -0.00309(18) -0.00239(19) 0.00160(18) Cl(1) 0.0265(6) 0.0275(6) 0.0348(7) 0.0032(4) -0.0016(4) -0.0115(4) Cl(2) 0.0265(6) 0.0221(5) 0.0510(8) -0.0086(4) 0.0026(5) -0.0133(5) N(1) 0.0188(19) 0.0157(16) 0.0203(18) -0.0046(13) 0.0041(14) -0.0023(13) C(1) 0.019(2) 0.0149(18) 0.021(2) -0.0060(15) 0.0050(16) -0.0022(14) C(2) 0.022(2) 0.0164(19) 0.016(2) -0.0071(16) 0.0050(16) -0.0045(15) C(3) 0.023(2) 0.022(2) 0.027(2) -0.0037(17) 0.0103(18) -0.0088(17) C(4) 0.031(2) 0.030(2) 0.027(2) -0.0090(19) 0.016(2) -0.0105(18) C(5) 0.026(2) 0.030(2) 0.016(2) -0.0131(18) 0.0035(17) -0.0062(16) C(6) 0.020(2) 0.021(2) 0.018(2) -0.0056(16) -0.0015(16) -0.0031(15) C(7) 0.013(2) 0.0177(19) 0.018(2) -0.0052(15) -0.0024(15) -0.0052(15) C(8) 0.0091(19) 0.0155(18) 0.020(2) -0.0042(13) -0.0026(15) -0.0022(14) C(9) 0.0084(19) 0.0171(19) 0.020(2) -0.0034(14) -0.0030(15) -0.0026(15) C(10) 0.012(2) 0.0209(19) 0.015(2) -0.0011(14) -0.0010(15) 0.0002(14) C(11) 0.024(2) 0.017(2) 0.026(2) -0.0024(16) 0.0083(18) -0.0054(16) C(12) 0.034(2) 0.021(2) 0.026(2) -0.0006(18) 0.0072(19) -0.0073(17) C(13) 0.020(2) 0.030(2) 0.020(2) 0.0014(17) 0.0039(17) -0.0015(17) C(14) 0.017(2) 0.029(2) 0.027(2) -0.0055(18) 0.0051(18) -0.0013(18) C(15) 0.014(2) 0.026(2) 0.024(2) -0.0065(16) 0.0013(16) -0.0052(16) C(16) 0.019(2) 0.0145(19) 0.022(2) -0.0037(15) 0.0009(17) 0.0037(15) C(17) 0.027(2) 0.025(2) 0.033(2) -0.0045(18) -0.017(2) -0.0032(19) C(18) 0.041(3) 0.022(2) 0.035(2) -0.001(2) -0.007(2) -0.0124(19) C(19) 0.017(2) 0.022(2) 0.025(2) -0.0013(16) -0.0043(17) -0.0033(17) C(20) 0.018(2) 0.025(2) 0.025(2) -0.0068(16) -0.0018(17) -0.0031(17) C(21) 0.019(2) 0.022(2) 0.019(2) -0.0041(16) -0.0001(16) -0.0007(15) C(22) 0.015(2) 0.0186(19) 0.016(2) -0.0037(15) 0.0029(15) -0.0040(15) C(23) 0.022(2) 0.017(2) 0.023(2) -0.0024(16) 0.0051(17) -0.0042(16) C(24) 0.022(2) 0.018(2) 0.026(2) -0.0011(16) 0.0029(18) -0.0061(16) C(25) 0.024(2) 0.018(2) 0.025(2) -0.0060(17) 0.0067(18) -0.0080(17) C(26) 0.017(2) 0.023(2) 0.022(2) -0.0037(16) 0.0035(16) -0.0084(16) C(27) 0.023(2) 0.019(2) 0.022(2) -0.0017(16) 0.0052(17) -0.0050(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cl Cl 0.148 0.159 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Se Se -0.093 2.226 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(1) Se(1) C(16) 96.79(17) yes . . . C(8) Se(2) C(22) 101.36(18) yes . . . C(1) N(1) C(2) 117.1(3) yes . . . Se(1) C(1) N(1) 116.7(2) yes . . . Se(1) C(1) C(9) 117.4(3) yes . . . N(1) C(1) C(9) 125.9(3) yes . . . N(1) C(2) C(3) 116.4(3) yes . . . N(1) C(2) C(7) 122.9(3) yes . . . C(3) C(2) C(7) 120.7(3) yes . . . C(2) C(3) C(4) 119.3(3) yes . . . C(3) C(4) C(5) 120.2(4) yes . . . C(4) C(5) C(6) 120.8(4) yes . . . C(5) C(6) C(7) 121.3(3) yes . . . C(2) C(7) C(6) 117.7(3) yes . . . C(2) C(7) C(8) 116.5(3) yes . . . C(6) C(7) C(8) 125.7(3) yes . . . Se(2) C(8) C(7) 120.4(2) yes . . . Se(2) C(8) C(9) 118.1(2) yes . . . C(7) C(8) C(9) 121.2(3) yes . . . C(1) C(9) C(8) 116.2(3) yes . . . C(1) C(9) C(10) 118.9(3) yes . . . C(8) C(9) C(10) 124.6(3) yes . . . C(9) C(10) C(11) 119.3(4) yes . . . C(9) C(10) C(15) 121.6(4) yes . . . C(11) C(10) C(15) 119.0(4) yes . . . C(10) C(11) C(12) 120.2(4) yes . . . C(11) C(12) C(13) 120.2(5) yes . . . C(12) C(13) C(14) 119.1(4) yes . . . C(13) C(14) C(15) 121.5(5) yes . . . C(10) C(15) C(14) 120.1(5) yes . . . Se(1) C(16) C(17) 121.8(3) yes . . . Se(1) C(16) C(21) 118.9(3) yes . . . C(17) C(16) C(21) 119.3(3) yes . . . C(16) C(17) C(18) 122.0(5) yes . . . C(17) C(18) C(19) 118.5(5) yes . . . Cl(1) C(19) C(18) 119.4(4) yes . . . Cl(1) C(19) C(20) 120.4(4) yes . . . C(18) C(19) C(20) 120.2(4) yes . . . C(19) C(20) C(21) 120.9(4) yes . . . C(16) C(21) C(20) 119.0(4) yes . . . Se(2) C(22) C(23) 114.4(3) yes . . . Se(2) C(22) C(27) 124.9(2) yes . . . C(23) C(22) C(27) 120.7(4) yes . . . C(22) C(23) C(24) 118.2(4) yes . . . C(23) C(24) C(25) 120.7(3) yes . . . Cl(2) C(25) C(24) 120.8(3) yes . . . Cl(2) C(25) C(26) 117.1(3) yes . . . C(24) C(25) C(26) 122.1(4) yes . . . C(25) C(26) C(27) 116.5(4) yes . . . C(22) C(27) C(26) 121.7(3) yes . . . C(2) C(3) H(1) 120.3 no . . . C(4) C(3) H(1) 120.3 no . . . C(3) C(4) H(2) 119.9 no . . . C(5) C(4) H(2) 119.9 no . . . C(4) C(5) H(3) 119.6 no . . . C(6) C(5) H(3) 119.6 no . . . C(5) C(6) H(4) 119.4 no . . . C(7) C(6) H(4) 119.4 no . . . C(10) C(11) H(5) 119.9 no . . . C(12) C(11) H(5) 119.9 no . . . C(11) C(12) H(6) 119.9 no . . . C(13) C(12) H(6) 119.9 no . . . C(12) C(13) H(7) 120.4 no . . . C(14) C(13) H(7) 120.4 no . . . C(13) C(14) H(8) 119.3 no . . . C(15) C(14) H(8) 119.3 no . . . C(10) C(15) H(9) 120.0 no . . . C(14) C(15) H(9) 120.0 no . . . C(16) C(17) H(10) 119.0 no . . . C(18) C(17) H(10) 119.0 no . . . C(17) C(18) H(11) 120.8 no . . . C(19) C(18) H(11) 120.8 no . . . C(19) C(20) H(12) 119.5 no . . . C(21) C(20) H(12) 119.5 no . . . C(16) C(21) H(13) 120.5 no . . . C(20) C(21) H(13) 120.5 no . . . C(22) C(23) H(14) 120.9 no . . . C(24) C(23) H(14) 120.9 no . . . C(23) C(24) H(15) 119.6 no . . . C(25) C(24) H(15) 119.6 no . . . C(25) C(26) H(16) 121.8 no . . . C(27) C(26) H(16) 121.8 no . . . C(22) C(27) H(17) 119.2 no . . . C(26) C(27) H(17) 119.1 no . . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Se(1) C(1) 1.936(4) yes . . Se(1) C(16) 1.906(4) yes . . Se(2) C(8) 1.928(3) yes . . Se(2) C(22) 1.931(4) yes . . Cl(1) C(19) 1.737(4) yes . . Cl(2) C(25) 1.750(5) yes . . N(1) C(1) 1.305(5) yes . . N(1) C(2) 1.378(5) yes . . C(1) C(9) 1.439(4) yes . . C(2) C(3) 1.418(6) yes . . C(2) C(7) 1.425(4) yes . . C(3) C(4) 1.381(6) yes . . C(4) C(5) 1.412(5) yes . . C(5) C(6) 1.366(6) yes . . C(6) C(7) 1.413(5) yes . . C(7) C(8) 1.429(5) yes . . C(8) C(9) 1.368(5) yes . . C(9) C(10) 1.488(5) yes . . C(10) C(11) 1.400(7) yes . . C(10) C(15) 1.376(7) yes . . C(11) C(12) 1.390(7) yes . . C(12) C(13) 1.390(7) yes . . C(13) C(14) 1.360(8) yes . . C(14) C(15) 1.393(6) yes . . C(16) C(17) 1.373(7) yes . . C(16) C(21) 1.420(7) yes . . C(17) C(18) 1.360(6) yes . . C(18) C(19) 1.422(8) yes . . C(19) C(20) 1.370(7) yes . . C(20) C(21) 1.374(5) yes . . C(22) C(23) 1.414(5) yes . . C(22) C(27) 1.358(6) yes . . C(23) C(24) 1.402(7) yes . . C(24) C(25) 1.342(7) yes . . C(25) C(26) 1.429(5) yes . . C(26) C(27) 1.405(7) yes . . C(3) H(1) 0.960 no . . C(4) H(2) 1.060 no . . C(5) H(3) 1.060 no . . C(6) H(4) 0.950 no . . C(11) H(5) 0.970 no . . C(12) H(6) 1.000 no . . C(13) H(7) 1.060 no . . C(14) H(8) 1.060 no . . C(15) H(9) 0.950 no . . C(17) H(10) 1.020 no . . C(18) H(11) 1.000 no . . C(20) H(12) 1.060 no . . C(21) H(13) 1.060 no . . C(23) H(14) 0.950 no . . C(24) H(15) 1.060 no . . C(26) H(16) 0.960 no . . C(27) H(17) 1.020 no . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cl(1) C(12) 3.557(4) ? . 1_365 Cl(1) C(13) 3.279(4) ? . 1_365 Cl(2) N(1) 3.573(4) ? . 1_545 N(1) Cl(2) 3.573(4) ? . 1_565 N(1) C(15) 3.322(7) ? . 1_455 C(1) C(14) 3.594(8) ? . 1_455 C(2) C(15) 3.598(7) ? . 1_455 C(12) Cl(1) 3.557(4) ? . 1_745 C(13) Cl(1) 3.279(4) ? . 1_745 C(14) C(1) 3.594(8) ? . 1_655 C(14) C(21) 3.531(6) ? . 2_675 C(15) N(1) 3.322(7) ? . 1_655 C(15) C(2) 3.598(7) ? . 1_655 C(21) C(14) 3.531(6) ? . 2_675 Se(1) H(8) 3.013 ? . 1_455 Se(1) H(12) 3.216 ? . 1_655 Se(1) H(13) 3.108 ? . 2_575 Se(2) H(3) 3.175 ? . 2_666 Se(2) H(4) 3.314 ? . 2_666 Se(2) H(16) 3.248 ? . 1_655 Se(2) H(17) 3.509 ? . 1_655 Cl(1) H(5) 2.919 ? . 1_465 Cl(1) H(6) 3.438 ? . 1_365 Cl(1) H(6) 3.353 ? . 1_465 Cl(1) H(6) 3.099 ? . 2_575 Cl(1) H(7) 2.919 ? . 1_365 Cl(1) H(10) 3.218 ? . 1_455 Cl(1) H(16) 3.546 ? . 1_465 Cl(2) H(1) 2.986 ? . 1_645 Cl(2) H(2) 3.413 ? . 1_645 Cl(2) H(10) 3.021 ? . 1_545 Cl(2) H(14) 3.287 ? . 1_455 Cl(2) H(15) 3.585 ? . 2_656 N(1) H(8) 3.466 ? . 1_455 N(1) H(9) 2.543 ? . 1_455 C(1) H(8) 2.979 ? . 1_455 C(1) H(9) 3.064 ? . 1_455 C(2) H(9) 2.920 ? . 1_455 C(3) H(9) 3.212 ? . 1_455 C(3) H(15) 3.096 ? . 1_465 C(4) H(14) 3.522 ? . 2_666 C(4) H(15) 3.437 ? . 1_465 C(5) H(3) 3.130 ? . 2_566 C(5) H(4) 3.329 ? . 2_566 C(5) H(14) 2.893 ? . 2_666 C(6) H(3) 3.000 ? . 2_566 C(6) H(14) 3.179 ? . 2_666 C(9) H(8) 3.404 ? . 1_455 C(10) H(8) 3.581 ? . 1_455 C(11) H(8) 3.400 ? . 1_455 C(11) H(11) 3.175 ? . 1_645 C(11) H(12) 3.236 ? . 2_575 C(12) H(11) 3.202 ? . 1_645 C(12) H(12) 2.822 ? . 2_575 C(13) H(12) 3.023 ? . 2_575 C(14) H(5) 3.440 ? . 1_655 C(14) H(12) 3.559 ? . 2_575 C(14) H(13) 3.253 ? . 1_655 C(14) H(13) 3.409 ? . 2_675 C(15) H(13) 3.451 ? . 1_655 C(16) H(7) 3.309 ? . 2_675 C(16) H(9) 3.592 ? . 1_455 C(16) H(12) 3.588 ? . 1_655 C(17) H(7) 3.433 ? . 2_675 C(17) H(16) 3.381 ? . 1_565 C(18) H(5) 3.497 ? . 1_465 C(18) H(6) 3.043 ? . 1_465 C(18) H(7) 3.440 ? . 2_675 C(18) H(16) 3.334 ? . 1_565 C(19) H(6) 3.248 ? . 1_465 C(19) H(7) 3.255 ? . 2_675 C(19) H(10) 3.576 ? . 1_455 C(20) H(7) 3.108 ? . 2_675 C(20) H(8) 3.316 ? . 2_675 C(21) H(7) 3.146 ? . 2_675 C(21) H(8) 3.447 ? . 1_455 C(21) H(8) 2.882 ? . 2_675 C(21) H(9) 3.341 ? . 1_455 C(21) H(13) 3.248 ? . 2_575 C(22) H(3) 3.423 ? . 2_566 C(22) H(11) 3.234 ? . 1_645 C(22) H(16) 3.446 ? . 1_655 C(23) H(2) 3.079 ? . 2_566 C(23) H(11) 3.454 ? . 1_645 C(23) H(16) 3.197 ? . 1_655 C(24) H(1) 3.192 ? . 1_645 C(24) H(2) 2.716 ? . 2_566 C(25) H(1) 3.366 ? . 1_645 C(25) H(2) 3.063 ? . 2_566 C(25) H(3) 3.427 ? . 2_566 C(25) H(10) 3.429 ? . 1_545 C(25) H(14) 3.471 ? . 1_455 C(26) H(3) 3.109 ? . 2_566 C(26) H(10) 3.216 ? . 1_545 C(26) H(11) 3.587 ? . 1_545 C(26) H(14) 3.208 ? . 1_455 C(27) H(3) 3.099 ? . 2_566 C(27) H(11) 3.444 ? . 1_645 H(1) Cl(2) 2.986 ? . 1_465 H(1) C(24) 3.192 ? . 1_465 H(1) C(25) 3.366 ? . 1_465 H(1) H(9) 3.136 ? . 1_455 H(1) H(15) 2.616 ? . 1_465 H(2) Cl(2) 3.413 ? . 1_465 H(2) C(23) 3.079 ? . 2_566 H(2) C(24) 2.716 ? . 2_566 H(2) C(25) 3.063 ? . 2_566 H(2) H(14) 3.378 ? . 2_566 H(2) H(15) 3.257 ? . 1_465 H(2) H(15) 2.868 ? . 2_566 H(3) Se(2) 3.175 ? . 2_666 H(3) C(5) 3.130 ? . 2_566 H(3) C(6) 3.000 ? . 2_566 H(3) C(22) 3.423 ? . 2_566 H(3) C(25) 3.427 ? . 2_566 H(3) C(26) 3.109 ? . 2_566 H(3) C(27) 3.099 ? . 2_566 H(3) H(3) 2.835 ? . 2_566 H(3) H(4) 2.585 ? . 2_566 H(3) H(14) 2.835 ? . 2_666 H(3) H(16) 3.446 ? . 2_566 H(3) H(17) 3.444 ? . 2_566 H(4) Se(2) 3.314 ? . 2_666 H(4) C(5) 3.329 ? . 2_566 H(4) H(3) 2.585 ? . 2_566 H(4) H(4) 3.027 ? . 2_666 H(4) H(14) 3.314 ? . 2_666 H(5) Cl(1) 2.919 ? . 1_645 H(5) C(14) 3.440 ? . 1_455 H(5) C(18) 3.497 ? . 1_645 H(5) H(7) 3.470 ? . 1_455 H(5) H(8) 3.124 ? . 1_455 H(5) H(11) 2.817 ? . 1_645 H(6) Cl(1) 3.353 ? . 1_645 H(6) Cl(1) 3.438 ? . 1_745 H(6) Cl(1) 3.099 ? . 2_575 H(6) C(18) 3.043 ? . 1_645 H(6) C(19) 3.248 ? . 1_645 H(6) H(6) 3.594 ? . 2_765 H(6) H(7) 2.926 ? . 2_765 H(6) H(11) 2.861 ? . 1_645 H(6) H(12) 3.016 ? . 2_575 H(7) Cl(1) 2.919 ? . 1_745 H(7) C(16) 3.309 ? . 2_675 H(7) C(17) 3.433 ? . 2_675 H(7) C(18) 3.440 ? . 2_675 H(7) C(19) 3.255 ? . 2_675 H(7) C(20) 3.108 ? . 2_675 H(7) C(21) 3.146 ? . 2_675 H(7) H(5) 3.470 ? . 1_655 H(7) H(6) 2.926 ? . 2_765 H(7) H(12) 3.362 ? . 2_575 H(7) H(12) 3.580 ? . 2_675 H(8) Se(1) 3.013 ? . 1_655 H(8) N(1) 3.466 ? . 1_655 H(8) C(1) 2.979 ? . 1_655 H(8) C(9) 3.404 ? . 1_655 H(8) C(10) 3.581 ? . 1_655 H(8) C(11) 3.400 ? . 1_655 H(8) C(20) 3.316 ? . 2_675 H(8) C(21) 3.447 ? . 1_655 H(8) C(21) 2.882 ? . 2_675 H(8) H(5) 3.124 ? . 1_655 H(8) H(12) 3.368 ? . 2_675 H(8) H(13) 2.755 ? . 1_655 H(8) H(13) 2.591 ? . 2_675 H(9) N(1) 2.543 ? . 1_655 H(9) C(1) 3.064 ? . 1_655 H(9) C(2) 2.920 ? . 1_655 H(9) C(3) 3.212 ? . 1_655 H(9) C(16) 3.592 ? . 1_655 H(9) C(21) 3.341 ? . 1_655 H(9) H(1) 3.136 ? . 1_655 H(9) H(13) 3.168 ? . 1_655 H(10) Cl(1) 3.218 ? . 1_655 H(10) Cl(2) 3.021 ? . 1_565 H(10) C(19) 3.576 ? . 1_655 H(10) C(25) 3.429 ? . 1_565 H(10) C(26) 3.216 ? . 1_565 H(10) H(16) 2.720 ? . 1_565 H(11) C(11) 3.175 ? . 1_465 H(11) C(12) 3.202 ? . 1_465 H(11) C(22) 3.234 ? . 1_465 H(11) C(23) 3.454 ? . 1_465 H(11) C(26) 3.587 ? . 1_565 H(11) C(27) 3.444 ? . 1_465 H(11) H(5) 2.817 ? . 1_465 H(11) H(6) 2.861 ? . 1_465 H(11) H(16) 2.654 ? . 1_565 H(12) Se(1) 3.216 ? . 1_455 H(12) C(11) 3.236 ? . 2_575 H(12) C(12) 2.822 ? . 2_575 H(12) C(13) 3.023 ? . 2_575 H(12) C(14) 3.559 ? . 2_575 H(12) C(16) 3.588 ? . 1_455 H(12) H(6) 3.016 ? . 2_575 H(12) H(7) 3.362 ? . 2_575 H(12) H(7) 3.580 ? . 2_675 H(12) H(8) 3.368 ? . 2_675 H(13) Se(1) 3.108 ? . 2_575 H(13) C(14) 3.253 ? . 1_455 H(13) C(14) 3.409 ? . 2_675 H(13) C(15) 3.451 ? . 1_455 H(13) C(21) 3.248 ? . 2_575 H(13) H(8) 2.755 ? . 1_455 H(13) H(8) 2.591 ? . 2_675 H(13) H(9) 3.168 ? . 1_455 H(13) H(13) 2.405 ? . 2_575 H(14) Cl(2) 3.287 ? . 1_655 H(14) C(4) 3.522 ? . 2_666 H(14) C(5) 2.893 ? . 2_666 H(14) C(6) 3.179 ? . 2_666 H(14) C(25) 3.471 ? . 1_655 H(14) C(26) 3.208 ? . 1_655 H(14) H(2) 3.378 ? . 2_566 H(14) H(3) 2.835 ? . 2_666 H(14) H(4) 3.314 ? . 2_666 H(14) H(16) 2.840 ? . 1_655 H(15) Cl(2) 3.585 ? . 2_656 H(15) C(3) 3.096 ? . 1_645 H(15) C(4) 3.437 ? . 1_645 H(15) H(1) 2.616 ? . 1_645 H(15) H(2) 3.257 ? . 1_645 H(15) H(2) 2.868 ? . 2_566 H(16) Se(2) 3.248 ? . 1_455 H(16) Cl(1) 3.546 ? . 1_645 H(16) C(17) 3.381 ? . 1_545 H(16) C(18) 3.334 ? . 1_545 H(16) C(22) 3.446 ? . 1_455 H(16) C(23) 3.197 ? . 1_455 H(16) H(3) 3.446 ? . 2_566 H(16) H(10) 2.720 ? . 1_545 H(16) H(11) 2.654 ? . 1_545 H(16) H(14) 2.840 ? . 1_455 H(17) Se(2) 3.509 ? . 1_455 H(17) H(3) 3.444 ? . 2_566 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(1) Se(1) C(16) C(17) 78.5(4) ? . . . . C(1) Se(1) C(16) C(21) -103.5(3) ? . . . . C(16) Se(1) C(1) N(1) -2.4(4) ? . . . . C(16) Se(1) C(1) C(9) 176.2(4) ? . . . . C(8) Se(2) C(22) C(23) -168.6(3) ? . . . . C(8) Se(2) C(22) C(27) 12.0(4) ? . . . . C(22) Se(2) C(8) C(7) 70.3(4) ? . . . . C(22) Se(2) C(8) C(9) -115.8(4) ? . . . . C(1) N(1) C(2) C(3) -174.2(4) ? . . . . C(1) N(1) C(2) C(7) 2.6(7) ? . . . . C(2) N(1) C(1) Se(1) 179.6(3) ? . . . . C(2) N(1) C(1) C(9) 1.1(7) ? . . . . Se(1) C(1) C(9) C(8) 177.9(3) ? . . . . Se(1) C(1) C(9) C(10) -7.8(6) ? . . . . N(1) C(1) C(9) C(8) -3.6(7) ? . . . . N(1) C(1) C(9) C(10) 170.7(5) ? . . . . N(1) C(2) C(3) C(4) 179.6(5) ? . . . . N(1) C(2) C(7) C(6) 179.6(4) ? . . . . N(1) C(2) C(7) C(8) -3.6(7) ? . . . . C(3) C(2) C(7) C(6) -3.6(7) ? . . . . C(3) C(2) C(7) C(8) 173.2(4) ? . . . . C(7) C(2) C(3) C(4) 2.7(8) ? . . . . C(2) C(3) C(4) C(5) 0.2(6) ? . . . . C(3) C(4) C(5) C(6) -2.2(9) ? . . . . C(4) C(5) C(6) C(7) 1.1(8) ? . . . . C(5) C(6) C(7) C(2) 1.7(7) ? . . . . C(5) C(6) C(7) C(8) -174.7(5) ? . . . . C(2) C(7) C(8) Se(2) 174.6(3) ? . . . . C(2) C(7) C(8) C(9) 0.8(7) ? . . . . C(6) C(7) C(8) Se(2) -8.9(7) ? . . . . C(6) C(7) C(8) C(9) 177.3(5) ? . . . . Se(2) C(8) C(9) C(1) -171.5(3) ? . . . . Se(2) C(8) C(9) C(10) 14.6(6) ? . . . . C(7) C(8) C(9) C(1) 2.4(7) ? . . . . C(7) C(8) C(9) C(10) -171.5(4) ? . . . . C(1) C(9) C(10) C(11) -106.6(4) ? . . . . C(1) C(9) C(10) C(15) 68.9(5) ? . . . . C(8) C(9) C(10) C(11) 67.2(6) ? . . . . C(8) C(9) C(10) C(15) -117.3(5) ? . . . . C(9) C(10) C(11) C(12) 175.9(3) ? . . . . C(9) C(10) C(15) C(14) -175.9(3) ? . . . . C(11) C(10) C(15) C(14) -0.4(5) ? . . . . C(15) C(10) C(11) C(12) 0.3(5) ? . . . . C(10) C(11) C(12) C(13) -0.1(5) ? . . . . C(11) C(12) C(13) C(14) 0.1(4) ? . . . . C(12) C(13) C(14) C(15) -0.2(5) ? . . . . C(13) C(14) C(15) C(10) 0.3(6) ? . . . . Se(1) C(16) C(17) C(18) 179.2(3) ? . . . . Se(1) C(16) C(21) C(20) -177.6(3) ? . . . . C(17) C(16) C(21) C(20) 0.4(6) ? . . . . C(21) C(16) C(17) C(18) 1.2(7) ? . . . . C(16) C(17) C(18) C(19) -2.1(7) ? . . . . C(17) C(18) C(19) Cl(1) -178.6(3) ? . . . . C(17) C(18) C(19) C(20) 1.4(7) ? . . . . Cl(1) C(19) C(20) C(21) -179.8(3) ? . . . . C(18) C(19) C(20) C(21) 0.2(6) ? . . . . C(19) C(20) C(21) C(16) -1.1(6) ? . . . . Se(2) C(22) C(23) C(24) -178.3(3) ? . . . . Se(2) C(22) C(27) C(26) 179.0(3) ? . . . . C(23) C(22) C(27) C(26) -0.4(6) ? . . . . C(27) C(22) C(23) C(24) 1.2(6) ? . . . . C(22) C(23) C(24) C(25) -2.6(7) ? . . . . C(23) C(24) C(25) Cl(2) -177.4(3) ? . . . . C(23) C(24) C(25) C(26) 3.1(7) ? . . . . Cl(2) C(25) C(26) C(27) 178.3(3) ? . . . . C(24) C(25) C(26) C(27) -2.2(7) ? . . . . C(25) C(26) C(27) C(22) 0.8(6) ? . . . . _journal_paper_doi 10.1039/c0ob01168a