#------------------------------------------------------------------------------ #$Date: 2012-02-28 14:14:52 +0200 (Tue, 28 Feb 2012) $ #$Revision: 35911 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/30/8103091.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_8103091 loop_ _publ_author_name 'Dao-Cheng Xia' 'Qiu-Ping Han' 'Shuang Han' 'Xin-Lu Cao' 'Yun-De Zhu' _publ_section_title ; Crystal structure of (1,4-bis((1H-imidazol-1-yl)methyl)benzene)-(5-hydroxyisophthalato)zinc(II), Zn(C14H14N4)(C8H4O5) ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 49 _journal_volume 226 _journal_year 2011 _chemical_formula_moiety 'C22 H18 N4 O5 Zn' _chemical_formula_sum 'C22 H18 N4 O5 Zn' _chemical_formula_weight 483.77 _chemical_melting_point ? _chemical_name_systematic ; (1,4-bis((1H-imidazol-1-yl)methyl)benzene)-(5-hydroxyisophthalato) zinc(II) ; _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 _audit_creation_method SHELXL-97 _audit_update_record ; 2010-10-20 # Formatted by publCIF ; _cell_angle_alpha 90.00 _cell_angle_beta 97.864(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.1529(4) _cell_length_b 9.6506(4) _cell_length_c 25.7059(10) _cell_measurement_reflns_used 3197 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.0860 _cell_measurement_theta_min 3.1601 _cell_volume 2003.53(15) _computing_cell_refinement CrysAlis _computing_data_collection CrysAlis _computing_data_reduction CrysAlis _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution SHELXS-97[2] _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.0 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.856 _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 8857 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 3.24 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96644 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.441 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4626 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.783 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0307 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.0638 _reflns_number_gt 2583 _reflns_number_total 4626 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file 1267-3278.cff _[local]_cod_data_source_block p21n _[local]_cod_cif_authors_sg_H-M p21/n _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 8103091 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_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 Zn01 Zn 0.63247(3) 0.24674(2) 0.690186(9) 0.03211(8) Uani 1 1 d . O5 O 0.4256(2) -0.17674(15) 0.48417(6) 0.0536(5) Uani 1 1 d . H5A H 0.4221 -0.2458 0.4655 0.080 Uiso 1 1 calc R O4 O 0.5213(2) 0.09696(13) 0.64693(6) 0.0376(4) Uani 1 1 d . O3 O 0.6064(2) -0.05143(15) 0.71118(6) 0.0543(5) Uani 1 1 d . O1 O 0.5664(2) -0.56417(14) 0.66708(6) 0.0463(4) Uani 1 1 d . O2 O 0.5844(3) -0.61636(17) 0.58500(7) 0.0943(8) Uani 1 1 d . N2 N 1.0537(2) 0.16701(19) 0.62513(7) 0.0387(5) Uani 1 1 d . N1 N 0.8652(2) 0.21768(17) 0.67554(7) 0.0366(5) Uani 1 1 d . C8 C 0.5502(3) -0.0261(2) 0.66522(9) 0.0336(5) Uani 1 1 d . N3 N 0.9685(3) 0.3080(2) 0.33374(7) 0.0462(5) Uani 1 1 d . C5 C 0.4794(3) -0.1104(2) 0.57298(8) 0.0339(5) Uani 1 1 d . H5 H 0.4638 -0.0186 0.5624 0.041 Uiso 1 1 calc R C6 C 0.5191(3) -0.1413(2) 0.62569(8) 0.0297(5) Uani 1 1 d . N4 N 1.0513(2) 0.24435(18) 0.25978(6) 0.0355(4) Uani 1 1 d . C2 C 0.5275(3) -0.3839(2) 0.60440(9) 0.0349(6) Uani 1 1 d . C12 C 1.1307(3) 0.1159(3) 0.58068(9) 0.0469(6) Uani 1 1 d . H12A H 1.1042 0.0183 0.5758 0.056 Uiso 1 1 calc R H12B H 1.2500 0.1233 0.5895 0.056 Uiso 1 1 calc R C7 C 0.5406(3) -0.27928(19) 0.64172(8) 0.0319(5) Uani 1 1 d . H7 H 0.5634 -0.3008 0.6772 0.038 Uiso 1 1 calc R C13 C 1.0796(3) 0.1899(2) 0.52937(9) 0.0370(6) Uani 1 1 d . C3 C 0.4891(3) -0.3502(2) 0.55144(9) 0.0421(6) Uani 1 1 d . H3 H 0.4812 -0.4202 0.5263 0.050 Uiso 1 1 calc R C16 C 0.9952(3) 0.3171(2) 0.43150(9) 0.0431(6) Uani 1 1 d . C15 C 0.9228(3) 0.3575(2) 0.47415(9) 0.0475(7) Uani 1 1 d . H15 H 0.8438 0.4276 0.4704 0.057 Uiso 1 1 calc R C17 C 1.1102(3) 0.2117(3) 0.43801(10) 0.0540(7) Uani 1 1 d . H17 H 1.1611 0.1828 0.4096 0.065 Uiso 1 1 calc R C4 C 0.4626(3) -0.2150(2) 0.53576(9) 0.0393(6) Uani 1 1 d . C10 C 1.0149(3) 0.2655(2) 0.69875(9) 0.0472(6) Uani 1 1 d . H10 H 1.0335 0.3115 0.7308 0.057 Uiso 1 1 calc R C14 C 0.9654(3) 0.2958(3) 0.52275(9) 0.0486(7) Uani 1 1 d . H14 H 0.9163 0.3263 0.5513 0.058 Uiso 1 1 calc R C19 C 0.9497(4) 0.3923(3) 0.37994(9) 0.0636(8) Uani 1 1 d . H19A H 0.8356 0.4230 0.3775 0.076 Uiso 1 1 calc R H19B H 1.0188 0.4741 0.3797 0.076 Uiso 1 1 calc R C1 C 0.5584(3) -0.5325(2) 0.61914(9) 0.0425(6) Uani 1 1 d . C18 C 1.1508(3) 0.1483(3) 0.48651(9) 0.0497(7) Uani 1 1 d . H18 H 1.2275 0.0764 0.4901 0.060 Uiso 1 1 calc R C22 C 0.9494(3) 0.1426(2) 0.27525(9) 0.0464(6) Uani 1 1 d . H22 H 0.9211 0.0603 0.2574 0.056 Uiso 1 1 calc R C20 C 1.0593(3) 0.3417(2) 0.29614(9) 0.0408(6) Uani 1 1 d . H20 H 1.1203 0.4230 0.2956 0.049 Uiso 1 1 calc R C9 C 0.8947(3) 0.1586(2) 0.63135(9) 0.0401(6) Uani 1 1 d . H9 H 0.8140 0.1163 0.6075 0.048 Uiso 1 1 calc R C21 C 0.8973(3) 0.1828(3) 0.32090(10) 0.0546(7) Uani 1 1 d . H21 H 0.8265 0.1341 0.3398 0.066 Uiso 1 1 calc R C11 C 1.1321(3) 0.2356(3) 0.66806(9) 0.0494(6) Uani 1 1 d . H11 H 1.2441 0.2573 0.6748 0.059 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 Zn01 0.04680(16) 0.02310(12) 0.02797(13) -0.00059(12) 0.01069(10) 0.00224(13) O5 0.0993(15) 0.0320(9) 0.0257(9) -0.0021(7) -0.0049(10) 0.0059(9) O4 0.0562(11) 0.0236(8) 0.0323(9) -0.0056(7) 0.0030(8) 0.0019(7) O3 0.1029(15) 0.0325(9) 0.0266(9) -0.0029(7) 0.0061(10) 0.0034(9) O1 0.0816(13) 0.0273(8) 0.0308(9) 0.0048(7) 0.0111(9) 0.0095(8) O2 0.212(3) 0.0308(10) 0.0365(11) -0.0046(9) 0.0040(14) 0.0265(13) N2 0.0427(13) 0.0499(12) 0.0250(10) -0.0003(9) 0.0098(10) 0.0069(9) N1 0.0442(12) 0.0375(11) 0.0295(10) 0.0000(8) 0.0097(9) 0.0023(9) C8 0.0466(15) 0.0235(11) 0.0331(14) -0.0018(10) 0.0141(12) 0.0009(10) N3 0.0656(15) 0.0473(12) 0.0279(11) 0.0065(9) 0.0147(11) 0.0049(11) C5 0.0488(16) 0.0220(10) 0.0311(13) 0.0009(10) 0.0065(12) 0.0039(10) C6 0.0419(14) 0.0214(10) 0.0266(12) -0.0018(9) 0.0082(11) 0.0016(10) N4 0.0497(11) 0.0323(9) 0.0252(9) 0.0056(9) 0.0071(8) -0.0033(10) C2 0.0528(16) 0.0243(11) 0.0272(13) -0.0009(10) 0.0036(12) 0.0026(10) C12 0.0508(17) 0.0598(16) 0.0316(13) -0.0015(12) 0.0108(13) 0.0127(13) C7 0.0433(14) 0.0282(12) 0.0251(11) 0.0015(9) 0.0080(10) 0.0016(9) C13 0.0383(15) 0.0455(13) 0.0287(13) -0.0034(10) 0.0097(11) 0.0001(11) C3 0.0698(18) 0.0253(11) 0.0298(13) -0.0078(10) 0.0019(13) 0.0053(12) C16 0.0562(17) 0.0453(14) 0.0303(13) 0.0017(11) 0.0145(13) 0.0004(12) C15 0.0614(18) 0.0457(14) 0.0372(14) 0.0035(12) 0.0130(13) 0.0111(13) C17 0.0640(19) 0.0686(18) 0.0339(14) 0.0029(12) 0.0227(14) 0.0151(14) C4 0.0604(17) 0.0300(13) 0.0270(12) -0.0001(9) 0.0035(12) 0.0036(10) C10 0.0539(16) 0.0555(16) 0.0320(12) -0.0112(12) 0.0054(12) 0.0003(14) C14 0.0613(18) 0.0570(16) 0.0305(14) -0.0049(11) 0.0171(13) 0.0039(13) C19 0.100(2) 0.0608(17) 0.0358(15) 0.0055(13) 0.0286(16) 0.0165(16) C1 0.0670(19) 0.0246(11) 0.0345(14) -0.0037(11) 0.0013(13) 0.0027(11) C18 0.0523(18) 0.0613(16) 0.0377(15) 0.0016(12) 0.0145(13) 0.0145(13) C22 0.0595(18) 0.0456(14) 0.0344(14) 0.0090(11) 0.0074(13) -0.0118(13) C20 0.0579(17) 0.0393(13) 0.0265(12) 0.0057(11) 0.0110(12) -0.0041(12) C9 0.0415(16) 0.0462(14) 0.0326(13) -0.0035(11) 0.0054(12) 0.0016(11) C21 0.0596(19) 0.0652(18) 0.0418(17) 0.0152(14) 0.0170(15) -0.0090(15) C11 0.0412(14) 0.0690(18) 0.0369(13) -0.0112(14) 0.0020(12) -0.0027(14) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 O4 Zn01 O1 115.09(7) . 1_565 O4 Zn01 N4 110.80(7) . 4_566 O1 Zn01 N4 96.88(7) 1_565 4_566 O4 Zn01 N1 99.55(7) . . O1 Zn01 N1 107.44(7) 1_565 . N4 Zn01 N1 127.89(7) 4_566 . C4 O5 H5A 109.5 . . C8 O4 Zn01 115.09(14) . . C1 O1 Zn01 119.59(14) . 1_545 C9 N2 C11 106.75(19) . . C9 N2 C12 127.1(2) . . C11 N2 C12 126.2(2) . . C9 N1 C10 105.3(2) . . C9 N1 Zn01 120.65(17) . . C10 N1 Zn01 133.19(15) . . O3 C8 O4 124.0(2) . . O3 C8 C6 120.50(18) . . O4 C8 C6 115.44(19) . . C20 N3 C21 107.5(2) . . C20 N3 C19 125.6(2) . . C21 N3 C19 126.9(2) . . C6 C5 C4 120.53(19) . . C6 C5 H5 119.7 . . C4 C5 H5 119.7 . . C5 C6 C7 119.83(18) . . C5 C6 C8 119.89(18) . . C7 C6 C8 120.15(19) . . C20 N4 C22 106.02(18) . . C20 N4 Zn01 127.91(15) . 4_665 C22 N4 Zn01 125.22(15) . 4_665 C7 C2 C3 119.44(19) . . C7 C2 C1 121.9(2) . . C3 C2 C1 118.63(18) . . N2 C12 C13 115.24(19) . . N2 C12 H12A 108.5 . . C13 C12 H12A 108.5 . . N2 C12 H12B 108.5 . . C13 C12 H12B 108.5 . . H12A C12 H12B 107.5 . . C2 C7 C6 119.7(2) . . C2 C7 H7 120.2 . . C6 C7 H7 120.2 . . C18 C13 C14 118.1(2) . . C18 C13 C12 117.8(2) . . C14 C13 C12 124.1(2) . . C4 C3 C2 120.9(2) . . C4 C3 H3 119.5 . . C2 C3 H3 119.5 . . C15 C16 C17 118.2(2) . . C15 C16 C19 118.9(2) . . C17 C16 C19 122.8(2) . . C16 C15 C14 121.1(2) . . C16 C15 H15 119.4 . . C14 C15 H15 119.4 . . C16 C17 C18 120.6(2) . . C16 C17 H17 119.7 . . C18 C17 H17 119.7 . . O5 C4 C3 123.01(19) . . O5 C4 C5 117.41(18) . . C3 C4 C5 119.5(2) . . C11 C10 N1 109.6(2) . . C11 C10 H10 125.2 . . N1 C10 H10 125.2 . . C13 C14 C15 120.8(2) . . C13 C14 H14 119.6 . . C15 C14 H14 119.6 . . N3 C19 C16 113.8(2) . . N3 C19 H19A 108.8 . . C16 C19 H19A 108.8 . . N3 C19 H19B 108.8 . . C16 C19 H19B 108.8 . . H19A C19 H19B 107.7 . . O2 C1 O1 123.0(2) . . O2 C1 C2 119.2(2) . . O1 C1 C2 117.65(19) . . C13 C18 C17 121.1(2) . . C13 C18 H18 119.5 . . C17 C18 H18 119.5 . . C21 C22 N4 108.5(2) . . C21 C22 H22 125.7 . . N4 C22 H22 125.7 . . N4 C20 N3 111.1(2) . . N4 C20 H20 124.4 . . N3 C20 H20 124.4 . . N1 C9 N2 111.8(2) . . N1 C9 H9 124.1 . . N2 C9 H9 124.1 . . C22 C21 N3 106.8(2) . . C22 C21 H21 126.6 . . N3 C21 H21 126.6 . . C10 C11 N2 106.5(2) . . C10 C11 H11 126.7 . . N2 C11 H11 126.7 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Zn01 O4 1.9677(14) . Zn01 O1 1.9712(14) 1_565 Zn01 N4 1.9925(16) 4_566 Zn01 N1 2.0040(19) . O5 C4 1.370(3) . O5 H5A 0.8200 . O4 C8 1.287(2) . O3 C8 1.232(3) . O1 C1 1.263(3) . O1 Zn01 1.9712(14) 1_545 O2 C1 1.234(3) . N2 C9 1.330(3) . N2 C11 1.368(3) . N2 C12 1.463(3) . N1 C9 1.322(3) . N1 C10 1.364(3) . C8 C6 1.504(3) . N3 C20 1.335(3) . N3 C21 1.362(3) . N3 C19 1.465(3) . C5 C6 1.382(3) . C5 C4 1.385(3) . C5 H5 0.9300 . C6 C7 1.398(3) . N4 C20 1.320(3) . N4 C22 1.380(3) . N4 Zn01 1.9925(16) 4_665 C2 C7 1.387(3) . C2 C3 1.393(3) . C2 C1 1.495(3) . C12 C13 1.508(3) . C12 H12A 0.9700 . C12 H12B 0.9700 . C7 H7 0.9300 . C13 C18 1.374(3) . C13 C14 1.378(3) . C3 C4 1.374(3) . C3 H3 0.9300 . C16 C15 1.371(3) . C16 C17 1.378(3) . C16 C19 1.512(3) . C15 C14 1.384(3) . C15 H15 0.9300 . C17 C18 1.388(3) . C17 H17 0.9300 . C10 C11 1.351(3) . C10 H10 0.9300 . C14 H14 0.9300 . C19 H19A 0.9700 . C19 H19B 0.9700 . C18 H18 0.9300 . C22 C21 1.358(3) . C22 H22 0.9300 . C20 H20 0.9300 . C9 H9 0.9300 . C21 H21 0.9300 . C11 H11 0.9300 . 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 O1 Zn01 O4 C8 -172.56(14) 1_565 N4 Zn01 O4 C8 -63.93(16) 4_566 N1 Zn01 O4 C8 72.97(15) . O4 Zn01 N1 C9 25.91(17) . O1 Zn01 N1 C9 -94.33(17) 1_565 N4 Zn01 N1 C9 151.86(15) 4_566 O4 Zn01 N1 C10 -166.0(2) . O1 Zn01 N1 C10 73.7(2) 1_565 N4 Zn01 N1 C10 -40.1(2) 4_566 Zn01 O4 C8 O3 17.7(3) . Zn01 O4 C8 C6 -159.21(15) . C4 C5 C6 C7 -0.8(4) . C4 C5 C6 C8 175.1(2) . O3 C8 C6 C5 -170.5(2) . O4 C8 C6 C5 6.5(3) . O3 C8 C6 C7 5.4(3) . O4 C8 C6 C7 -177.57(19) . C9 N2 C12 C13 67.1(3) . C11 N2 C12 C13 -111.5(3) . C3 C2 C7 C6 -1.6(4) . C1 C2 C7 C6 176.6(2) . C5 C6 C7 C2 2.3(3) . C8 C6 C7 C2 -173.7(2) . N2 C12 C13 C18 178.6(2) . N2 C12 C13 C14 -1.9(4) . C7 C2 C3 C4 -0.5(4) . C1 C2 C3 C4 -178.8(2) . C17 C16 C15 C14 0.9(4) . C19 C16 C15 C14 -177.3(2) . C15 C16 C17 C18 0.2(4) . C19 C16 C17 C18 178.3(3) . C2 C3 C4 O5 179.6(2) . C2 C3 C4 C5 2.0(4) . C6 C5 C4 O5 -179.0(2) . C6 C5 C4 C3 -1.3(4) . C9 N1 C10 C11 0.5(3) . Zn01 N1 C10 C11 -168.85(16) . C18 C13 C14 C15 0.5(4) . C12 C13 C14 C15 -179.0(2) . C16 C15 C14 C13 -1.3(4) . C20 N3 C19 C16 -124.6(3) . C21 N3 C19 C16 55.8(4) . C15 C16 C19 N3 -153.3(2) . C17 C16 C19 N3 28.6(4) . Zn01 O1 C1 O2 2.7(4) 1_545 Zn01 O1 C1 C2 -172.88(16) 1_545 C7 C2 C1 O2 -162.8(3) . C3 C2 C1 O2 15.4(4) . C7 C2 C1 O1 13.0(4) . C3 C2 C1 O1 -168.8(2) . C14 C13 C18 C17 0.6(4) . C12 C13 C18 C17 -179.9(2) . C16 C17 C18 C13 -0.9(4) . C20 N4 C22 C21 0.5(3) . Zn01 N4 C22 C21 -169.60(17) 4_665 C22 N4 C20 N3 -0.1(3) . Zn01 N4 C20 N3 169.65(15) 4_665 C21 N3 C20 N4 -0.3(3) . C19 N3 C20 N4 180.0(2) . C10 N1 C9 N2 -0.4(2) . Zn01 N1 C9 N2 170.59(14) . C11 N2 C9 N1 0.1(3) . C12 N2 C9 N1 -178.69(19) . N4 C22 C21 N3 -0.7(3) . C20 N3 C21 C22 0.6(3) . C19 N3 C21 C22 -179.7(2) . N1 C10 C11 N2 -0.4(3) . C9 N2 C11 C10 0.2(3) . C12 N2 C11 C10 179.0(2) .