#------------------------------------------------------------------------------ #$Date: 2014-06-06 07:58:26 +0300 (Fri, 06 Jun 2014) $ #$Revision: 116015 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/64/7216409.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_7216409 loop_ _publ_author_name 'Guo, Huadong' 'GUO, Xianmin' 'zou, hengye' 'Qi, Yanjuan' 'Chen, Ruizhan' 'Zhao, lun' 'Chunming, Liu' _publ_section_title ; A series of coordination polymers assembled by 9,9-dimethylfluorene-2,7-dicarboxylic acid and various flexible bis(imidazole) ligands: synthesis, structures and properties ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/c4ce00664j _journal_year 2014 _chemical_formula_moiety 'C22 H19 N2 O4 Zn' _chemical_formula_sum 'C22 H19 N2 O4 Zn' _chemical_formula_weight 440.76 _chemical_melting_point ? _chemical_name_systematic ; ? ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.1497(19) _cell_length_b 10.9266(9) _cell_length_c 18.6978(16) _cell_measurement_reflns_used 5311 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.02 _cell_measurement_theta_min 1.61 _cell_volume 4321.0(6) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 9.00cm _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 26291 _diffrn_reflns_theta_full 28.27 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_number none _exptl_absorpt_coefficient_mu 1.165 _exptl_absorpt_correction_T_max 0.760 _exptl_absorpt_correction_T_min 0.710 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1816 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.492 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 5311 _refine_ls_number_restraints 510 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0513 _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^)+(0.0652P)^2^+1.9853P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1206 _refine_ls_wR_factor_ref 0.1486 _reflns_number_gt 2910 _reflns_number_total 5311 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4ce00664j2.cif _[local]_cod_data_source_block cncnc1 _[local]_cod_cif_authors_sg_H-M Pbcn _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 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 7216409 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, 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 C1 C 0.34881(18) 0.2884(4) 0.4668(2) 0.0524(9) Uani 1 1 d U C2 C 0.29487(17) 0.3338(3) 0.42143(19) 0.0471(8) Uani 1 1 d U C3 C 0.25065(17) 0.4131(3) 0.45001(19) 0.0524(9) Uani 1 1 d U H3 H 0.2533 0.4353 0.4979 0.063 Uiso 1 1 calc R C4 C 0.20248(17) 0.4597(3) 0.40812(19) 0.0510(8) Uani 1 1 d U H4 H 0.1728 0.5131 0.4274 0.061 Uiso 1 1 calc R C5 C 0.19916(16) 0.4254(3) 0.33674(18) 0.0452(8) Uani 1 1 d U C6 C 0.24283(17) 0.3436(3) 0.30779(18) 0.0476(8) Uani 1 1 d U C7 C 0.29103(17) 0.2983(3) 0.34993(19) 0.0512(8) Uani 1 1 d U H7 H 0.3207 0.2446 0.3308 0.061 Uiso 1 1 calc R C8 C 0.15623(16) 0.4640(3) 0.27958(18) 0.0438(8) Uani 1 1 d U C9 C 0.10699(16) 0.5484(3) 0.27998(19) 0.0493(8) Uani 1 1 d U H9 H 0.0947 0.5869 0.3221 0.059 Uiso 1 1 calc R C10 C 0.07673(17) 0.5735(3) 0.21574(19) 0.0504(9) Uani 1 1 d U H10 H 0.0442 0.6308 0.2150 0.060 Uiso 1 1 calc R C11 C 0.09368(16) 0.5155(3) 0.15308(18) 0.0441(8) Uani 1 1 d U C12 C 0.14272(16) 0.4286(3) 0.15276(19) 0.0492(8) Uani 1 1 d U H12 H 0.1538 0.3879 0.1109 0.059 Uiso 1 1 calc R C13 C 0.17383(16) 0.4052(3) 0.21599(18) 0.0461(8) Uani 1 1 d U C14 C 0.22842(18) 0.3172(3) 0.22934(19) 0.0521(9) Uani 1 1 d U C15 C 0.2051(2) 0.1843(4) 0.2206(2) 0.0772(13) Uani 1 1 d U H15A H 0.2396 0.1289 0.2287 0.116 Uiso 1 1 calc R H15B H 0.1890 0.1730 0.1730 0.116 Uiso 1 1 calc R H15C H 0.1721 0.1684 0.2546 0.116 Uiso 1 1 calc R C16 C 0.28440(19) 0.3402(4) 0.1800(2) 0.0709(12) Uani 1 1 d U H16A H 0.3173 0.2823 0.1902 0.106 Uiso 1 1 calc R H16B H 0.3000 0.4217 0.1874 0.106 Uiso 1 1 calc R H16C H 0.2712 0.3312 0.1311 0.106 Uiso 1 1 calc R C17 C 0.44148(17) -0.0447(3) 0.5864(2) 0.0507(9) Uani 1 1 d . C18 C 0.5711(3) 0.2974(6) 0.5580(3) 0.1072(17) Uani 1 1 d U H18 H 0.6017 0.2471 0.5377 0.129 Uiso 1 1 calc R C19 C 0.5827(3) 0.3982(7) 0.5963(3) 0.1213(17) Uani 1 1 d U H19 H 0.6222 0.4310 0.6069 0.146 Uiso 1 1 calc R C20 C 0.4821(3) 0.3699(5) 0.5891(3) 0.0924(14) Uani 1 1 d U H20 H 0.4388 0.3814 0.5947 0.111 Uiso 1 1 calc R C21 C 0.5134(4) 0.5572(7) 0.6569(4) 0.1439(19) Uani 1 1 d U C22 C 0.5312(6) 0.5954(13) 0.7181(7) 0.124(3) Uani 0.50 1 d PU C22' C 0.4817(7) 0.4979(12) 0.7325(7) 0.120(3) Uani 0.50 1 d PU N1 N 0.5257(3) 0.4436(5) 0.6166(2) 0.1064(16) Uani 1 1 d . N2 N 0.50694(17) 0.2798(4) 0.55337(18) 0.0699(10) Uani 1 1 d . O1 O 0.39326(12) 0.2336(2) 0.43229(13) 0.0611(7) Uani 1 1 d . O2 O 0.34902(14) 0.3045(3) 0.53153(15) 0.0743(9) Uani 1 1 d . O3 O 0.42949(12) 0.0128(2) 0.52953(13) 0.0562(7) Uani 1 1 d . O4 O 0.48158(13) -0.1293(3) 0.58948(15) 0.0705(8) Uani 1 1 d . Zn1 Zn 0.46009(2) 0.16639(4) 0.48976(2) 0.05128(17) Uani 1 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 0.051(2) 0.056(2) 0.051(2) -0.0036(17) -0.0096(16) 0.0111(17) C2 0.0464(18) 0.0482(18) 0.0467(18) -0.0025(16) -0.0067(14) 0.0095(16) C3 0.0526(19) 0.061(2) 0.0436(18) -0.0069(16) -0.0048(16) 0.0128(17) C4 0.0466(18) 0.0570(19) 0.0495(18) -0.0101(16) -0.0025(15) 0.0155(15) C5 0.0422(17) 0.0456(17) 0.0477(17) -0.0075(15) -0.0064(14) 0.0082(14) C6 0.0495(17) 0.0462(17) 0.0472(16) -0.0079(15) -0.0100(14) 0.0128(15) C7 0.0510(18) 0.0497(18) 0.0528(18) -0.0086(15) -0.0087(15) 0.0201(15) C8 0.0390(16) 0.0455(17) 0.0468(17) -0.0057(14) -0.0082(14) 0.0070(14) C9 0.0420(17) 0.0540(19) 0.0520(18) -0.0098(16) -0.0047(15) 0.0117(15) C10 0.0394(18) 0.052(2) 0.060(2) -0.0072(17) -0.0061(16) 0.0154(16) C11 0.0391(17) 0.0437(18) 0.0497(19) -0.0053(15) -0.0076(14) 0.0071(15) C12 0.0473(18) 0.0496(18) 0.0507(18) -0.0119(15) -0.0088(15) 0.0128(15) C13 0.0419(17) 0.0460(17) 0.0503(17) -0.0075(15) -0.0095(14) 0.0126(14) C14 0.0556(19) 0.0510(19) 0.0498(18) -0.0104(15) -0.0129(15) 0.0209(16) C15 0.097(3) 0.057(3) 0.078(3) -0.018(2) -0.036(2) 0.025(2) C16 0.066(3) 0.087(3) 0.060(2) -0.012(2) -0.008(2) 0.037(2) C17 0.043(2) 0.055(2) 0.054(2) -0.0009(19) 0.0051(17) 0.0086(18) C18 0.081(3) 0.135(4) 0.106(4) -0.025(3) -0.005(3) -0.013(3) C19 0.107(4) 0.150(4) 0.107(4) -0.027(3) -0.005(3) -0.033(3) C20 0.091(3) 0.112(3) 0.074(3) -0.029(3) -0.006(2) -0.017(3) C21 0.149(4) 0.158(4) 0.125(4) -0.056(4) 0.006(4) -0.036(4) C22 0.134(5) 0.138(5) 0.100(5) -0.025(5) -0.013(5) -0.029(5) C22' 0.123(5) 0.133(5) 0.103(5) -0.030(5) -0.016(5) -0.017(5) N1 0.130(4) 0.119(4) 0.070(3) -0.031(3) 0.009(3) -0.037(3) N2 0.057(2) 0.092(3) 0.060(2) -0.007(2) -0.0109(18) 0.001(2) O1 0.0557(16) 0.0761(18) 0.0517(15) -0.0096(14) -0.0172(13) 0.0279(15) O2 0.074(2) 0.102(2) 0.0472(16) -0.0037(15) -0.0107(14) 0.0311(17) O3 0.0510(15) 0.0681(18) 0.0495(15) 0.0008(14) 0.0080(12) 0.0117(13) O4 0.0666(18) 0.0769(19) 0.0680(18) 0.0069(15) 0.0200(15) 0.0352(16) Zn1 0.0465(3) 0.0624(3) 0.0449(3) -0.0038(2) -0.00382(19) 0.0213(2) 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 O2 C1 O1 124.1(3) . . O2 C1 C2 120.9(3) . . O1 C1 C2 115.1(3) . . C3 C2 C7 120.4(3) . . C3 C2 C1 120.1(3) . . C7 C2 C1 119.5(3) . . C2 C3 C4 120.7(3) . . C2 C3 H3 119.7 . . C4 C3 H3 119.7 . . C3 C4 C5 118.9(3) . . C3 C4 H4 120.6 . . C5 C4 H4 120.6 . . C4 C5 C6 120.8(3) . . C4 C5 C8 130.9(3) . . C6 C5 C8 108.2(3) . . C7 C6 C5 119.8(3) . . C7 C6 C14 129.0(3) . . C5 C6 C14 111.2(3) . . C6 C7 C2 119.4(3) . . C6 C7 H7 120.3 . . C2 C7 H7 120.3 . . C9 C8 C13 120.5(3) . . C9 C8 C5 130.6(3) . . C13 C8 C5 108.8(3) . . C10 C9 C8 118.1(3) . . C10 C9 H9 120.9 . . C8 C9 H9 120.9 . . C11 C10 C9 121.6(3) . . C11 C10 H10 119.2 . . C9 C10 H10 119.2 . . C10 C11 C12 120.3(3) . . C10 C11 C17 119.0(3) . 2_554 C12 C11 C17 120.7(3) . 2_554 C13 C12 C11 118.3(3) . . C13 C12 H12 120.9 . . C11 C12 H12 120.9 . . C12 C13 C8 121.1(3) . . C12 C13 C14 128.3(3) . . C8 C13 C14 110.6(3) . . C16 C14 C13 112.7(3) . . C16 C14 C6 113.4(3) . . C13 C14 C6 100.9(3) . . C16 C14 C15 109.9(3) . . C13 C14 C15 109.5(3) . . C6 C14 C15 110.1(3) . . C14 C15 H15A 109.5 . . C14 C15 H15B 109.5 . . H15A C15 H15B 109.5 . . C14 C15 H15C 109.5 . . H15A C15 H15C 109.5 . . H15B C15 H15C 109.5 . . C14 C16 H16A 109.5 . . C14 C16 H16B 109.5 . . H16A C16 H16B 109.5 . . C14 C16 H16C 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . O4 C17 O3 122.8(3) . . O4 C17 C11 117.2(3) . 2 O3 C17 C11 120.0(3) . 2 C19 C18 N2 109.4(6) . . C19 C18 H18 125.3 . . N2 C18 H18 125.3 . . C18 C19 N1 106.7(6) . . C18 C19 H19 126.6 . . N1 C19 H19 126.6 . . N2 C20 N1 112.1(5) . . N2 C20 H20 124.0 . . N1 C20 H20 124.0 . . C22 C21 N1 133.0(10) . . C22 C21 C22' 59.5(7) . . N1 C21 C22' 100.1(7) . . C21 C22 C22' 106.1(11) . 4_656 C21 C22 C22' 74.1(8) . . C22' C22 C22' 39.9(9) 4_656 . C21 C22 C22 112.5(12) . 4_656 C22' C22 C22 55.1(8) 4_656 4_656 C22' C22 C22 50.9(8) . 4_656 C22' C22' C22 74.4(12) 4_656 4_656 C22' C22' C22 65.7(12) 4_656 . C22 C22' C22 74.0(12) 4_656 . C22' C22' C21 103.7(19) 4_656 . C22 C22' C21 109.1(10) 4_656 . C22 C22' C21 46.4(7) . . C20 N1 C19 106.7(5) . . C20 N1 C21 125.8(6) . . C19 N1 C21 127.3(6) . . C20 N2 C18 105.1(5) . . C20 N2 Zn1 125.4(3) . . C18 N2 Zn1 128.3(4) . . C1 O1 Zn1 115.7(2) . . C17 O3 Zn1 133.2(3) . . C17 O4 Zn1 122.7(3) . 5_656 O1 Zn1 O3 107.39(12) . . O1 Zn1 O4 96.82(12) . 5_656 O3 Zn1 O4 108.55(11) . 5_656 O1 Zn1 N2 117.65(13) . . O3 Zn1 N2 118.41(13) . . O4 Zn1 N2 105.47(15) 5_656 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 O2 1.223(4) . C1 O1 1.288(4) . C1 C2 1.506(5) . C2 C3 1.382(5) . C2 C7 1.394(5) . C3 C4 1.382(5) . C3 H3 0.9300 . C4 C5 1.388(5) . C4 H4 0.9300 . C5 C6 1.395(5) . C5 C8 1.465(4) . C6 C7 1.380(5) . C6 C14 1.526(5) . C7 H7 0.9300 . C8 C9 1.391(5) . C8 C13 1.402(5) . C9 C10 1.388(5) . C9 H9 0.9300 . C10 C11 1.379(5) . C10 H10 0.9300 . C11 C12 1.407(5) . C11 C17 1.486(5) 2_554 C12 C13 1.377(4) . C12 H12 0.9300 . C13 C14 1.523(5) . C14 C16 1.522(6) . C14 C15 1.543(5) . C15 H15A 0.9600 . C15 H15B 0.9600 . C15 H15C 0.9600 . C16 H16A 0.9600 . C16 H16B 0.9600 . C16 H16C 0.9600 . C17 O4 1.256(4) . C17 O3 1.261(4) . C17 C11 1.486(5) 2 C18 C19 1.336(8) . C18 N2 1.373(6) . C18 H18 0.9300 . C19 N1 1.357(8) . C19 H19 0.9300 . C20 N2 1.301(6) . C20 N1 1.328(6) . C20 H20 0.9300 . C21 C22 1.276(12) . C21 N1 1.475(8) . C21 C22' 1.694(16) . C22 C22' 1.435(17) 4_656 C22 C22' 1.517(18) . C22 C22 1.78(3) 4_656 C22' C22' 1.01(2) 4_656 C22' C22 1.435(17) 4_656 N2 Zn1 1.983(4) . O1 Zn1 1.922(2) . O3 Zn1 1.946(3) . O4 Zn1 1.970(3) 5_656 Zn1 O4 1.970(3) 5_656 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_4 O2 C1 C2 C3 11.7(6) . . O1 C1 C2 C3 -167.9(4) . . O2 C1 C2 C7 -170.3(4) . . O1 C1 C2 C7 10.1(5) . . C7 C2 C3 C4 -0.8(6) . . C1 C2 C3 C4 177.2(3) . . C2 C3 C4 C5 0.1(6) . . C3 C4 C5 C6 1.2(6) . . C3 C4 C5 C8 -176.5(4) . . C4 C5 C6 C7 -1.7(6) . . C8 C5 C6 C7 176.5(3) . . C4 C5 C6 C14 178.3(3) . . C8 C5 C6 C14 -3.5(4) . . C5 C6 C7 C2 0.9(6) . . C14 C6 C7 C2 -179.1(4) . . C3 C2 C7 C6 0.3(6) . . C1 C2 C7 C6 -177.7(3) . . C4 C5 C8 C9 1.4(7) . . C6 C5 C8 C9 -176.5(4) . . C4 C5 C8 C13 178.1(4) . . C6 C5 C8 C13 0.2(4) . . C13 C8 C9 C10 -0.9(6) . . C5 C8 C9 C10 175.4(4) . . C8 C9 C10 C11 1.2(6) . . C9 C10 C11 C12 0.0(6) . . C9 C10 C11 C17 178.8(3) . 2_554 C10 C11 C12 C13 -1.4(6) . . C17 C11 C12 C13 179.9(3) 2_554 . C11 C12 C13 C8 1.6(6) . . C11 C12 C13 C14 -179.3(4) . . C9 C8 C13 C12 -0.5(6) . . C5 C8 C13 C12 -177.6(3) . . C9 C8 C13 C14 -179.7(3) . . C5 C8 C13 C14 3.2(4) . . C12 C13 C14 C16 54.7(5) . . C8 C13 C14 C16 -126.2(3) . . C12 C13 C14 C6 175.9(4) . . C8 C13 C14 C6 -4.9(4) . . C12 C13 C14 C15 -68.0(5) . . C8 C13 C14 C15 111.2(4) . . C7 C6 C14 C16 -54.1(5) . . C5 C6 C14 C16 125.8(3) . . C7 C6 C14 C13 -174.9(4) . . C5 C6 C14 C13 5.1(4) . . C7 C6 C14 C15 69.4(5) . . C5 C6 C14 C15 -110.6(4) . . N2 C18 C19 N1 0.7(7) . . N1 C21 C22 C22' -50.0(16) . 4_656 C22' C21 C22 C22' 24.2(11) . 4_656 N1 C21 C22 C22' -74.2(12) . . N1 C21 C22 C22 -108.3(11) . 4_656 C22' C21 C22 C22 -34.1(7) . 4_656 C21 C22 C22' C22' 142.1(18) . 4_656 C22 C22 C22' C22' -79.8(16) 4_656 4_656 C21 C22 C22' C22 -138.1(12) . 4_656 C22' C22 C22' C22 79.8(16) 4_656 4_656 C22' C22 C22' C21 -142.1(18) 4_656 . C22 C22 C22' C21 138.1(12) 4_656 . C22 C21 C22' C22' -35.1(11) . 4_656 N1 C21 C22' C22' 99.3(9) . 4_656 C22 C21 C22' C22 42.8(14) . 4_656 N1 C21 C22' C22 177.2(9) . 4_656 N1 C21 C22' C22 134.4(10) . . N2 C20 N1 C19 0.8(7) . . N2 C20 N1 C21 176.9(5) . . C18 C19 N1 C20 -0.9(7) . . C18 C19 N1 C21 -176.9(6) . . C22 C21 N1 C20 126.4(12) . . C22' C21 N1 C20 69.0(8) . . C22 C21 N1 C19 -58.3(14) . . C22' C21 N1 C19 -115.7(7) . . N1 C20 N2 C18 -0.3(6) . . N1 C20 N2 Zn1 -168.5(3) . . C19 C18 N2 C20 -0.3(7) . . C19 C18 N2 Zn1 167.4(4) . . O2 C1 O1 Zn1 4.0(5) . . C2 C1 O1 Zn1 -176.4(2) . . O4 C17 O3 Zn1 -95.3(4) . . C11 C17 O3 Zn1 86.3(4) 2 . O3 C17 O4 Zn1 9.6(6) . 5_656 C11 C17 O4 Zn1 -172.1(3) 2 5_656 C1 O1 Zn1 O3 79.0(3) . . C1 O1 Zn1 O4 -169.1(3) . 5_656 C1 O1 Zn1 N2 -57.6(3) . . C17 O3 Zn1 O1 -150.5(3) . . C17 O3 Zn1 O4 105.8(3) . 5_656 C17 O3 Zn1 N2 -14.3(4) . . C20 N2 Zn1 O1 38.1(5) . . C18 N2 Zn1 O1 -127.2(4) . . C20 N2 Zn1 O3 -93.7(4) . . C18 N2 Zn1 O3 100.9(4) . . C20 N2 Zn1 O4 144.6(4) . 5_656 C18 N2 Zn1 O4 -20.7(5) . 5_656