#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202196.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202196 loop_ _publ_author_name 'Li, Qing-Xiang' 'Li, Yi-Zhi' 'Luo, Qin-Hui' _publ_section_title ; [1-(Benzimidazol-2-ylmethyl)-1,4,7-triazacyclononane]chlorocopper(II) perchlorate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m23 _journal_page_last m25 _journal_paper_doi 10.1107/S1600536802022183 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac '[Cu Cl (C14 H21 N5)] Cl O4' _chemical_formula_moiety 'C14 H21 Cl Cu N5 1+, Cl O4 1-' _chemical_formula_sum 'C14 H21 Cl2 Cu N5 O4' _chemical_formula_weight 457.80 _chemical_name_systematic ; [1-(benzimidazol-2-ylmethyl)-1,4,7-triazacyclononane]chlorocopper(II) perchlorate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 99.56(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3360(10) _cell_length_b 13.4280(10) _cell_length_c 13.0510(10) _cell_measurement_reflns_used 3169 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.11 _cell_measurement_theta_min 2.19 _cell_volume 1786.2(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2000)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9413 _diffrn_reflns_theta_full 25.53 _diffrn_reflns_theta_max 25.53 _diffrn_reflns_theta_min 2.19 _exptl_absorpt_coefficient_mu 1.554 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_correction_T_min 0.696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 940 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.387 _refine_diff_density_min -0.375 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3334 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0355 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.02P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.0686 _reflns_number_gt 2636 _reflns_number_total 3334 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6129.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202196 _cod_database_fobs_code 2202196 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu1 0.23747(3) 0.13246(2) 0.06117(2) 0.03019(11) Uani d . 1 . . Cu C1 0.1721(3) 0.2367(2) -0.1315(2) 0.0371(7) Uani d . 1 . . C H1A 0.1686 0.1755 -0.1713 0.044 Uiso calc R 1 . . H H1B 0.1772 0.2920 -0.1785 0.044 Uiso calc R 1 . . H C2 0.0489(3) 0.2463(2) -0.0828(2) 0.0423(7) Uani d . 1 . . C H2A 0.0391 0.3148 -0.0618 0.051 Uiso calc R 1 . . H H2B -0.0272 0.2290 -0.1338 0.051 Uiso calc R 1 . . H C3 0.0126(3) 0.2279(2) 0.1007(2) 0.0435(7) Uani d . 1 . . C H3A 0.0031 0.1775 0.1522 0.052 Uiso calc R 1 . . H H3B -0.0719 0.2596 0.0797 0.052 Uiso calc R 1 . . H C4 0.1122(3) 0.3046(2) 0.1475(2) 0.0417(7) Uani d . 1 . . C H4A 0.1062 0.3628 0.1030 0.050 Uiso calc R 1 . . H H4B 0.0933 0.3252 0.2148 0.050 Uiso calc R 1 . . H C5 0.3439(3) 0.32758(19) 0.1218(2) 0.0369(7) Uani d . 1 . . C H5A 0.4311 0.3004 0.1436 0.044 Uiso calc R 1 . . H H5B 0.3415 0.3936 0.1516 0.044 Uiso calc R 1 . . H C6 0.3151(3) 0.33456(18) 0.0034(2) 0.0352(7) Uani d . 1 . . C H6A 0.2394 0.3772 -0.0166 0.042 Uiso calc R 1 . . H H6B 0.3892 0.3658 -0.0207 0.042 Uiso calc R 1 . . H C7 0.4076(2) 0.19580(19) -0.08532(19) 0.0319(6) Uani d . 1 . . C H7A 0.4586 0.2494 -0.1087 0.038 Uiso calc R 1 . . H H7B 0.3827 0.1499 -0.1426 0.038 Uiso calc R 1 . . H C8 0.4861(2) 0.14320(17) 0.0048(2) 0.0291(6) Uani d . 1 . . C C9 0.6456(3) 0.07650(18) 0.1162(2) 0.0307(6) Uani d . 1 . . C C10 0.7629(3) 0.04328(19) 0.1738(2) 0.0387(7) Uani d . 1 . . C H10 0.8421 0.0494 0.1494 0.046 Uiso calc R 1 . . H C11 0.7562(3) 0.0011(2) 0.2684(2) 0.0393(7) Uani d . 1 . . C H11 0.8329 -0.0215 0.3092 0.047 Uiso calc R 1 . . H C12 0.6370(3) -0.00916(19) 0.3053(2) 0.0374(7) Uani d . 1 . . C H12 0.6367 -0.0381 0.3700 0.045 Uiso calc R 1 . . H C13 0.5205(3) 0.02273(18) 0.2478(2) 0.0333(6) Uani d . 1 . . C H13 0.4414 0.0152 0.2721 0.040 Uiso calc R 1 . . H C14 0.5255(2) 0.06622(17) 0.1528(2) 0.0275(6) Uani d . 1 . . C Cl1 0.19564(7) 0.12846(5) 0.42264(5) 0.03870(18) Uani d . 1 . . Cl Cl2 0.17144(7) -0.02020(5) 0.10957(6) 0.04058(19) Uani d . 1 . . Cl N1 0.2891(2) 0.23624(14) -0.04973(15) 0.0289(5) Uani d . 1 . . N N2 0.0552(2) 0.18025(16) 0.00899(17) 0.0375(6) Uani d . 1 . . N H2C 0.0032 0.1263 -0.0096 0.045 Uiso calc R 1 . . H N3 0.2460(2) 0.26316(15) 0.15981(16) 0.0327(5) Uani d . 1 . . N H3C 0.2743 0.2460 0.2273 0.039 Uiso calc R 1 . . H N4 0.4272(2) 0.10768(14) 0.07971(16) 0.0276(5) Uani d . 1 . . N N5 0.6146(2) 0.12552(14) 0.02192(16) 0.0321(5) Uani d . 1 . . N H5C 0.6689 0.1417 -0.0185 0.039 Uiso calc R 1 . . H O1 0.0874(2) 0.09044(18) 0.3521(2) 0.0821(8) Uani d . 1 . . O O2 0.2275(2) 0.22619(14) 0.38811(16) 0.0527(6) Uani d . 1 . . O O3 0.3077(2) 0.06580(15) 0.42705(18) 0.0605(6) Uani d . 1 . . O O4 0.1611(2) 0.13810(16) 0.52315(16) 0.0654(7) Uani d . 1 . . O 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 Cu1 0.02534(19) 0.02599(18) 0.0389(2) -0.00025(14) 0.00432(14) 0.00384(15) C1 0.0405(17) 0.0346(15) 0.0329(16) 0.0049(13) -0.0034(13) 0.0030(13) C2 0.0339(17) 0.0436(17) 0.0457(18) 0.0061(13) -0.0038(14) 0.0051(14) C3 0.0289(16) 0.0483(18) 0.055(2) 0.0097(14) 0.0135(14) 0.0102(15) C4 0.0462(19) 0.0384(17) 0.0430(18) 0.0112(14) 0.0147(15) 0.0017(14) C5 0.0412(18) 0.0279(14) 0.0404(17) -0.0030(12) 0.0031(14) -0.0017(13) C6 0.0409(17) 0.0238(14) 0.0413(17) -0.0020(12) 0.0084(14) 0.0004(12) C7 0.0326(16) 0.0349(15) 0.0288(15) -0.0007(12) 0.0067(12) 0.0016(12) C8 0.0295(15) 0.0260(14) 0.0317(15) 0.0004(12) 0.0046(12) -0.0013(12) C9 0.0331(16) 0.0252(14) 0.0332(16) -0.0017(12) 0.0040(13) 0.0011(12) C10 0.0272(16) 0.0378(16) 0.0510(19) -0.0004(13) 0.0061(14) 0.0023(14) C11 0.0363(17) 0.0347(16) 0.0425(18) 0.0038(13) -0.0070(14) 0.0005(14) C12 0.0472(19) 0.0306(15) 0.0320(16) 0.0009(13) -0.0002(14) 0.0048(12) C13 0.0352(16) 0.0289(14) 0.0363(16) -0.0009(12) 0.0072(13) 0.0010(12) C14 0.0290(15) 0.0205(13) 0.0329(16) -0.0006(11) 0.0051(12) 0.0003(11) Cl1 0.0373(4) 0.0345(4) 0.0447(4) 0.0033(3) 0.0078(3) 0.0027(3) Cl2 0.0387(4) 0.0314(4) 0.0523(5) -0.0053(3) 0.0092(3) 0.0065(3) N1 0.0284(12) 0.0263(11) 0.0314(12) 0.0012(9) 0.0036(10) 0.0046(10) N2 0.0262(13) 0.0359(13) 0.0489(15) -0.0019(10) 0.0014(11) 0.0042(11) N3 0.0373(14) 0.0304(12) 0.0302(13) 0.0007(10) 0.0052(10) 0.0006(10) N4 0.0274(12) 0.0256(11) 0.0302(12) -0.0015(9) 0.0065(10) 0.0025(9) N5 0.0283(13) 0.0351(13) 0.0351(13) -0.0005(10) 0.0118(10) 0.0053(10) O1 0.0628(17) 0.0709(16) 0.103(2) -0.0015(13) -0.0152(15) -0.0297(15) O2 0.0663(15) 0.0397(12) 0.0589(14) 0.0049(10) 0.0302(12) 0.0092(10) O3 0.0528(14) 0.0521(13) 0.0802(17) 0.0189(11) 0.0221(13) 0.0082(12) O4 0.0733(17) 0.0779(17) 0.0516(15) 0.0238(13) 0.0299(13) 0.0254(12) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables 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 N4 Cu1 N2 164.01(9) N4 Cu1 N1 80.64(8) N2 Cu1 N1 83.55(8) N4 Cu1 N3 97.04(8) N2 Cu1 N3 83.43(9) N1 Cu1 N3 83.37(8) N4 Cu1 Cl2 98.75(6) N2 Cu1 Cl2 94.26(7) N1 Cu1 Cl2 153.09(6) N3 Cu1 Cl2 123.14(6) N1 C1 C2 110.0(2) N1 C1 H1A 109.7 C2 C1 H1A 109.7 N1 C1 H1B 109.7 C2 C1 H1B 109.7 H1A C1 H1B 108.2 N2 C2 C1 111.1(2) N2 C2 H2A 109.4 C1 C2 H2A 109.4 N2 C2 H2B 109.4 C1 C2 H2B 109.4 H2A C2 H2B 108.0 N2 C3 C4 110.3(2) N2 C3 H3A 109.6 C4 C3 H3A 109.6 N2 C3 H3B 109.6 C4 C3 H3B 109.6 H3A C3 H3B 108.1 N3 C4 C3 110.5(2) N3 C4 H4A 109.6 C3 C4 H4A 109.6 N3 C4 H4B 109.6 C3 C4 H4B 109.6 H4A C4 H4B 108.1 N3 C5 C6 110.3(2) N3 C5 H5A 109.6 C6 C5 H5A 109.6 N3 C5 H5B 109.6 C6 C5 H5B 109.6 H5A C5 H5B 108.1 N1 C6 C5 113.9(2) N1 C6 H6A 108.8 C5 C6 H6A 108.8 N1 C6 H6B 108.8 C5 C6 H6B 108.8 H6A C6 H6B 107.7 N1 C7 C8 107.21(19) N1 C7 H7A 110.3 C8 C7 H7A 110.3 N1 C7 H7B 110.3 C8 C7 H7B 110.3 H7A C7 H7B 108.5 N4 C8 N5 112.3(2) N4 C8 C7 119.8(2) N5 C8 C7 127.9(2) C10 C9 N5 133.2(2) C10 C9 C14 121.6(2) N5 C9 C14 105.2(2) C11 C10 C9 116.7(3) C11 C10 H10 121.6 C9 C10 H10 121.6 C10 C11 C12 122.0(3) C10 C11 H11 119.0 C12 C11 H11 119.0 C13 C12 C11 121.4(3) C13 C12 H12 119.3 C11 C12 H12 119.3 C12 C13 C14 117.5(3) C12 C13 H13 121.3 C14 C13 H13 121.3 C13 C14 N4 130.9(2) C13 C14 C9 120.9(2) N4 C14 C9 108.2(2) O4 Cl1 O1 109.83(16) O4 Cl1 O3 110.08(14) O1 Cl1 O3 111.18(15) O4 Cl1 O2 108.10(13) O1 Cl1 O2 108.70(15) O3 Cl1 O2 108.88(13) C1 N1 C7 113.32(19) C1 N1 C6 113.2(2) C7 N1 C6 112.0(2) C1 N1 Cu1 103.02(15) C7 N1 Cu1 106.57(14) C6 N1 Cu1 107.90(15) C2 N2 C3 114.4(2) C2 N2 Cu1 112.28(16) C3 N2 Cu1 104.60(16) C2 N2 H2C 108.4 C3 N2 H2C 108.4 Cu1 N2 H2C 108.4 C4 N3 C5 115.1(2) C4 N3 Cu1 107.21(16) C5 N3 Cu1 103.69(14) C4 N3 H3C 110.2 C5 N3 H3C 110.2 Cu1 N3 H3C 110.2 C8 N4 C14 106.2(2) C8 N4 Cu1 114.84(17) C14 N4 Cu1 138.90(17) C8 N5 C9 108.1(2) C8 N5 H5C 126.0 C9 N5 H5C 126.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 N4 . 1.964(2) ? Cu1 N2 . 2.000(2) ? Cu1 N1 . 2.1398(19) ? Cu1 N3 . 2.170(2) ? Cu1 Cl2 . 2.2827(7) ? C1 N1 . 1.475(3) ? C1 C2 . 1.520(4) ? C1 H1A . 0.9700 ? C1 H1B . 0.9700 ? C2 N2 . 1.483(3) ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C3 N2 . 1.486(3) ? C3 C4 . 1.512(4) ? C3 H3A . 0.9700 ? C3 H3B . 0.9700 ? C4 N3 . 1.475(3) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 N3 . 1.479(3) ? C5 C6 . 1.527(4) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 N1 . 1.495(3) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 N1 . 1.483(3) ? C7 C8 . 1.491(3) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 N4 . 1.323(3) ? C8 N5 . 1.331(3) ? C9 C10 . 1.390(4) ? C9 N5 . 1.385(3) ? C9 C14 . 1.408(3) ? C10 C11 . 1.370(4) ? C10 H10 . 0.9300 ? C11 C12 . 1.402(4) ? C11 H11 . 0.9300 ? C12 C13 . 1.378(4) ? C12 H12 . 0.9300 ? C13 C14 . 1.379(3) ? C13 H13 . 0.9300 ? C14 N4 . 1.389(3) ? Cl1 O4 . 1.422(2) ? Cl1 O1 . 1.420(2) ? Cl1 O3 . 1.425(2) ? Cl1 O2 . 1.4433(19) ? N2 H2C . 0.9100 ? N3 H3C . 0.9100 ? N5 H5C . 0.8600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2C Cl2 3_555 0.91 2.49 3.361(2) 160 N3 H3C O2 1_555 0.91 2.25 3.058(3) 148 N5 H5C O2 4_665 0.86 2.29 3.009(3) 141 N5 H5C Cl2 3_655 0.86 2.73 3.331(2) 128 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 N1 C1 C2 N2 -44.1(3) N2 C3 C4 N3 -47.5(3) N3 C5 C6 N1 -47.3(3) N1 C7 C8 N4 25.0(3) N1 C7 C8 N5 -155.1(2) N5 C9 C10 C11 176.9(3) C14 C9 C10 C11 -0.7(4) C9 C10 C11 C12 0.5(4) C10 C11 C12 C13 0.2(4) C11 C12 C13 C14 -0.7(4) C12 C13 C14 N4 -177.9(2) C12 C13 C14 C9 0.6(4) C10 C9 C14 C13 0.1(4) N5 C9 C14 C13 -178.0(2) C10 C9 C14 N4 178.9(2) N5 C9 C14 N4 0.8(3) C2 C1 N1 C7 161.7(2) C2 C1 N1 C6 -69.3(3) C2 C1 N1 Cu1 47.0(2) C8 C7 N1 C1 -146.3(2) C8 C7 N1 C6 84.1(2) C8 C7 N1 Cu1 -33.7(2) C5 C6 N1 C1 132.9(2) C5 C6 N1 C7 -97.5(3) C5 C6 N1 Cu1 19.5(3) N4 Cu1 N1 C1 147.32(16) N2 Cu1 N1 C1 -30.29(15) N3 Cu1 N1 C1 -114.39(16) Cl2 Cu1 N1 C1 56.4(2) N4 Cu1 N1 C7 27.79(15) N2 Cu1 N1 C7 -149.81(16) N3 Cu1 N1 C7 126.09(16) Cl2 Cu1 N1 C7 -63.1(2) N4 Cu1 N1 C6 -92.67(16) N2 Cu1 N1 C6 89.72(16) N3 Cu1 N1 C6 5.62(16) Cl2 Cu1 N1 C6 176.42(12) C1 C2 N2 C3 135.4(2) C1 C2 N2 Cu1 16.4(3) C4 C3 N2 C2 -70.3(3) C4 C3 N2 Cu1 53.0(2) N4 Cu1 N2 C2 -0.7(4) N1 Cu1 N2 C2 7.89(17) N3 Cu1 N2 C2 91.92(18) Cl2 Cu1 N2 C2 -145.17(17) N4 Cu1 N2 C3 -125.4(3) N1 Cu1 N2 C3 -116.76(17) N3 Cu1 N2 C3 -32.74(16) Cl2 Cu1 N2 C3 90.17(16) C3 C4 N3 C5 132.4(2) C3 C4 N3 Cu1 17.7(3) C6 C5 N3 C4 -69.2(3) C6 C5 N3 Cu1 47.6(2) N4 Cu1 N3 C4 172.69(16) N2 Cu1 N3 C4 8.78(16) N1 Cu1 N3 C4 93.02(16) Cl2 Cu1 N3 C4 -82.02(16) N4 Cu1 N3 C5 50.46(16) N2 Cu1 N3 C5 -113.44(16) N1 Cu1 N3 C5 -29.20(16) Cl2 Cu1 N3 C5 155.75(13) N5 C8 N4 C14 1.9(3) C7 C8 N4 C14 -178.3(2) N5 C8 N4 Cu1 179.17(16) C7 C8 N4 Cu1 -0.9(3) C13 C14 N4 C8 177.0(3) C9 C14 N4 C8 -1.6(3) C13 C14 N4 Cu1 0.7(4) C9 C14 N4 Cu1 -177.86(18) N2 Cu1 N4 C8 -6.7(4) N1 Cu1 N4 C8 -15.41(17) N3 Cu1 N4 C8 -97.46(18) Cl2 Cu1 N4 C8 137.34(16) N2 Cu1 N4 C14 169.3(3) N1 Cu1 N4 C14 160.7(3) N3 Cu1 N4 C14 78.6(2) Cl2 Cu1 N4 C14 -46.6(2) N4 C8 N5 C9 -1.4(3) C7 C8 N5 C9 178.7(2) C10 C9 N5 C8 -177.5(3) C14 C9 N5 C8 0.3(3)