#------------------------------------------------------------------------------ #$Date: 2020-08-25 04:36:20 +0300 (Tue, 25 Aug 2020) $ #$Revision: 255617 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705261.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_7705261 loop_ _publ_author_name 'Xu, Bo-Wei' 'Niu, Ru-Jie' 'Liu, Quan' 'Yang, Junyi' 'Zhang, Wen-Hua' 'Young, David James' _publ_section_title ; Similarities and differences between Mn(II) and Zn(II) coordination polymers supported by porphyrin-based ligands: Synthesis, structures and nonlinear optical properties ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02450C _journal_year 2020 _chemical_formula_moiety 'C44 H32 N8 O4 Zn' _chemical_formula_sum 'C44 H32 N8 O4 Zn' _chemical_formula_weight 802.14 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2013 _audit_update_record ; 2020-06-16 deposited with the CCDC. 2020-08-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.554(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.8328(13) _cell_length_b 9.1345(12) _cell_length_c 20.405(3) _cell_measurement_reflns_used 3506 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.57 _cell_measurement_theta_min 2.45 _cell_volume 1781.7(4) _computing_cell_refinement 'Bruker D8 Quest' _computing_data_collection 'Bruker D8 Quest' _computing_data_reduction 'Bruker D8 Quest' _computing_molecular_graphics 'SHELXL-2013 (Sheldrick, 2013)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_unetI/netI 0.0960 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 9343 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.513 _diffrn_reflns_theta_min 2.053 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.749 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector Data), version 2008/1; University of G\"ottingen: G\"ottingen, Germany, 2008. ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.495 _exptl_crystal_description block _exptl_crystal_F_000 828 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.680 _refine_diff_density_min -0.957 _refine_diff_density_rms 0.151 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4034 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0640 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+1.1459P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1694 _refine_ls_wR_factor_ref 0.2069 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2726 _reflns_number_total 4034 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02450c2.cif _cod_data_source_block ZN-THPP _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7705261 _publcif_datablock.id {985ec8c6-b69b-4e93-a8e2-22e60a491081} _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.779 _shelx_estimated_absorpt_t_max 0.915 _shelxl_version_number 2013-2 _shelx_res_file ; TITL POR-ZN in P2(1)/c CELL 0.71073 9.8328 9.1345 20.4046 90.000 103.554 90.000 ZERR 2.00 0.0013 0.0012 0.0031 0.000 0.005 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O ZN UNIT 88 64 16 8 2 TEMP -153.120 SIZE 0.12 0.30 0.35 L.S. 20 BOND $H ACTA FMAP 2 PLAN 4 DFIX 0.83 0.02 O1 H1O1 O2 H1O2 WGHT 0.104000 1.145900 FVAR 0.18157 ZN1 5 0.000000 1.000000 0.500000 10.50000 0.03508 0.01586 = 0.01425 -0.00225 -0.00216 0.00535 O1 4 -0.165389 0.638257 0.031185 11.00000 0.05145 0.03059 = 0.02136 0.00265 0.00713 -0.00068 AFIX 3 H1O1 2 -0.178209 0.733598 0.012145 11.00000 -1.20000 AFIX 0 O2 4 0.610195 0.156856 0.672397 11.00000 0.09850 0.06716 = 0.06092 -0.01197 -0.01574 0.04288 AFIX 3 H1O2 2 0.643095 0.072816 0.677357 11.00000 -1.20000 AFIX 0 N1 3 -0.272898 0.635939 0.189587 11.00000 0.04879 0.05375 = 0.02597 -0.01880 0.01458 -0.02423 N2 3 0.305078 0.308341 0.573153 11.00000 0.04293 0.02637 = 0.04303 0.00545 0.00960 0.01114 N3 3 -0.137716 1.059122 0.410886 11.00000 0.03475 0.01671 = 0.01267 -0.00048 0.00027 0.00319 N4 3 0.056529 0.817373 0.454781 11.00000 0.03065 0.01515 = 0.01733 -0.00120 0.00231 0.00138 C1 1 -0.251992 0.602233 0.075070 11.00000 0.03833 0.02790 = 0.02370 -0.00676 0.00562 -0.00602 AFIX 23 H1A 2 -0.253510 0.494610 0.080581 11.00000 -1.20000 H1B 2 -0.348759 0.634987 0.054976 11.00000 -1.20000 AFIX 0 C2 1 -0.200910 0.673318 0.143608 11.00000 0.03525 0.02300 = 0.01908 -0.00295 0.00188 0.00060 C3 1 -0.087351 0.765050 0.158325 11.00000 0.04110 0.02496 = 0.01923 -0.00198 0.01183 -0.00436 AFIX 43 H3 2 -0.036374 0.786983 0.125340 11.00000 -1.20000 AFIX 0 C4 1 -0.234279 0.698299 0.250536 11.00000 0.05378 0.04773 = 0.02315 -0.01341 0.01432 -0.02276 AFIX 43 H4 2 -0.286426 0.674745 0.282853 11.00000 -1.20000 AFIX 0 C5 1 -0.123597 0.794659 0.269574 11.00000 0.03664 0.01794 = 0.01618 -0.00408 0.00109 0.00106 C6 1 -0.048663 0.825017 0.222409 11.00000 0.04185 0.02659 = 0.01968 -0.00400 0.00524 -0.01044 AFIX 43 H6 2 0.030476 0.887701 0.233733 11.00000 -1.20000 AFIX 0 C7 1 0.501424 0.154739 0.618293 11.00000 0.06516 0.06602 = 0.05037 0.00598 -0.00258 0.03572 AFIX 23 H7A 2 0.429367 0.085566 0.626144 11.00000 -1.20000 H7B 2 0.533233 0.121182 0.578225 11.00000 -1.20000 AFIX 0 C8 1 0.438521 0.309246 0.605640 11.00000 0.06168 0.03347 = 0.02577 0.00310 0.01079 0.02077 C9 1 0.513044 0.438548 0.624074 11.00000 0.03814 0.06224 = 0.02511 -0.00435 -0.00164 0.02368 AFIX 43 H9 2 0.608430 0.436140 0.647874 11.00000 -1.20000 AFIX 0 C10 1 0.444422 0.571185 0.606793 11.00000 0.03303 0.03674 = 0.03200 -0.00395 -0.00186 0.00821 AFIX 43 H10 2 0.493579 0.660825 0.617542 11.00000 -1.20000 AFIX 0 C11 1 0.304943 0.572073 0.574039 11.00000 0.03165 0.02050 = 0.01935 -0.00049 0.00147 0.00669 C12 1 0.240811 0.436493 0.560140 11.00000 0.03248 0.02433 = 0.03301 0.00043 0.00713 0.00605 AFIX 43 H12 2 0.143477 0.435376 0.539755 11.00000 -1.20000 AFIX 0 C13 1 -0.213231 1.185711 0.398487 11.00000 0.03584 0.01676 = 0.01818 -0.00030 0.00243 0.00128 C14 1 -0.281281 1.195410 0.327698 11.00000 0.03743 0.02651 = 0.02050 0.00317 -0.00549 0.01067 AFIX 43 H14 2 -0.340246 1.272066 0.305973 11.00000 -1.20000 AFIX 0 C15 1 -0.244050 1.073125 0.298529 11.00000 0.04657 0.02604 = 0.01743 -0.00062 -0.00133 0.00935 AFIX 43 H15 2 -0.272874 1.047701 0.252195 11.00000 -1.20000 AFIX 0 C16 1 -0.153259 0.989007 0.350249 11.00000 0.03670 0.02077 = 0.01583 0.00022 -0.00084 0.00263 C17 1 -0.086537 0.858706 0.339317 11.00000 0.03401 0.01945 = 0.01279 -0.00339 0.00101 -0.00125 C18 1 0.013286 0.781876 0.387414 11.00000 0.03172 0.01688 = 0.01657 -0.00273 0.00182 -0.00063 C19 1 0.085034 0.654117 0.373974 11.00000 0.04516 0.02316 = 0.01839 -0.00446 0.00240 0.00750 AFIX 43 H19 2 0.074487 0.607677 0.331419 11.00000 -1.20000 AFIX 0 C20 1 0.170604 0.610803 0.432408 11.00000 0.04024 0.02345 = 0.02255 -0.00312 0.00404 0.00671 AFIX 43 H20 2 0.231879 0.528929 0.438805 11.00000 -1.20000 AFIX 0 C21 1 0.150931 0.713759 0.483792 11.00000 0.03039 0.01673 = 0.01901 -0.00098 0.00533 0.00178 C22 1 0.221402 0.707253 0.552450 11.00000 0.03064 0.01587 = 0.02202 0.00013 0.00235 0.00185 EQIV $1 -x, y+1/2, -z+1/2 HTAB O1 N2_$1 EQIV $2 x+1, -y+1/2, z+1/2 HTAB O2 N1_$2 HKLF 4 REM POR-ZN in P2(1)/c REM R1 = 0.0640 for 2726 Fo > 4sig(Fo) and 0.1065 for all 4034 data REM 259 parameters refined using 2 restraints END WGHT 0.1042 1.1363 REM Highest difference peak 0.680, deepest hole -0.957, 1-sigma level 0.151 Q1 1 0.5827 0.2362 0.6379 11.00000 0.05 0.68 Q2 1 0.5017 0.0800 0.6663 11.00000 0.05 0.68 Q3 1 0.5045 0.0558 0.5968 11.00000 0.05 0.56 Q4 1 -0.2034 0.7852 0.2449 11.00000 0.05 0.55 ; _shelx_res_checksum 1506 _publcif_funding_html ; ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 1.0000 0.5000 0.0230(2) Uani 1 2 d S . P . . O1 O -0.1654(3) 0.6383(3) 0.03118(14) 0.0347(8) Uani 1 1 d D . . . . H1O1 H -0.1782 0.7336 0.0121 0.042 Uiso 1 1 d DR U . . . O2 O 0.6102(5) 0.1569(5) 0.6724(2) 0.0812(16) Uani 1 1 d D . . . . H1O2 H 0.6431 0.0728 0.6774 0.097 Uiso 1 1 d DR U . . . N1 N -0.2729(4) 0.6359(5) 0.18959(19) 0.0419(11) Uani 1 1 d . . . . . N2 N 0.3051(4) 0.3083(4) 0.5732(2) 0.0375(10) Uani 1 1 d . . . . . N3 N -0.1377(4) 1.0591(4) 0.41089(15) 0.0223(7) Uani 1 1 d . . . . . N4 N 0.0565(3) 0.8174(3) 0.45478(16) 0.0216(7) Uani 1 1 d . . . . . C1 C -0.2520(5) 0.6022(5) 0.0751(2) 0.0302(10) Uani 1 1 d . . . . . H1A H -0.2535 0.4946 0.0806 0.036 Uiso 1 1 calc R U . . . H1B H -0.3488 0.6350 0.0550 0.036 Uiso 1 1 calc R U . . . C2 C -0.2009(5) 0.6733(5) 0.1436(2) 0.0265(9) Uani 1 1 d . . . . . C3 C -0.0874(5) 0.7651(5) 0.1583(2) 0.0276(9) Uani 1 1 d . . . . . H3 H -0.0364 0.7870 0.1253 0.033 Uiso 1 1 calc R U . . . C4 C -0.2343(6) 0.6983(6) 0.2505(2) 0.0407(12) Uani 1 1 d . . . . . H4 H -0.2864 0.6747 0.2829 0.049 Uiso 1 1 calc R U . . . C5 C -0.1236(5) 0.7947(4) 0.26957(19) 0.0244(9) Uani 1 1 d . . . . . C6 C -0.0487(5) 0.8250(5) 0.2224(2) 0.0297(10) Uani 1 1 d . . . . . H6 H 0.0305 0.8877 0.2337 0.036 Uiso 1 1 calc R U . . . C7 C 0.5014(7) 0.1547(7) 0.6183(3) 0.0632(18) Uani 1 1 d . . . . . H7A H 0.4294 0.0856 0.6261 0.076 Uiso 1 1 calc R U . . . H7B H 0.5332 0.1212 0.5782 0.076 Uiso 1 1 calc R U . . . C8 C 0.4385(6) 0.3092(5) 0.6056(2) 0.0402(12) Uani 1 1 d . . . . . C9 C 0.5130(5) 0.4385(6) 0.6241(2) 0.0433(13) Uani 1 1 d . . . . . H9 H 0.6084 0.4361 0.6479 0.052 Uiso 1 1 calc R U . . . C10 C 0.4444(5) 0.5712(5) 0.6068(2) 0.0355(11) Uani 1 1 d . . . . . H10 H 0.4936 0.6608 0.6175 0.043 Uiso 1 1 calc R U . . . C11 C 0.3049(4) 0.5721(4) 0.57404(19) 0.0246(9) Uani 1 1 d . . . . . C12 C 0.2408(5) 0.4365(5) 0.5601(2) 0.0300(10) Uani 1 1 d . . . . . H12 H 0.1435 0.4354 0.5398 0.036 Uiso 1 1 calc R U . . . C13 C -0.2132(5) 1.1857(4) 0.3985(2) 0.0242(9) Uani 1 1 d . . . . . C14 C -0.2813(5) 1.1954(5) 0.3277(2) 0.0302(10) Uani 1 1 d . . . . . H14 H -0.3402 1.2721 0.3060 0.036 Uiso 1 1 calc R U . . . C15 C -0.2441(5) 1.0731(5) 0.2985(2) 0.0315(10) Uani 1 1 d . . . . . H15 H -0.2729 1.0477 0.2522 0.038 Uiso 1 1 calc R U . . . C16 C -0.1533(5) 0.9890(4) 0.3502(2) 0.0256(9) Uani 1 1 d . . . . . C17 C -0.0865(4) 0.8587(4) 0.33932(18) 0.0228(8) Uani 1 1 d . . . . . C18 C 0.0133(4) 0.7819(4) 0.38741(19) 0.0224(8) Uani 1 1 d . . . . . C19 C 0.0850(5) 0.6541(5) 0.3740(2) 0.0297(10) Uani 1 1 d . . . . . H19 H 0.0745 0.6077 0.3314 0.036 Uiso 1 1 calc R U . . . C20 C 0.1706(5) 0.6108(5) 0.4324(2) 0.0293(10) Uani 1 1 d . . . . . H20 H 0.2319 0.5289 0.4388 0.035 Uiso 1 1 calc R U . . . C21 C 0.1509(4) 0.7138(4) 0.4838(2) 0.0221(8) Uani 1 1 d . . . . . C22 C 0.2214(4) 0.7073(4) 0.5524(2) 0.0235(9) 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 Zn1 0.0351(4) 0.0159(3) 0.0142(3) -0.0023(2) -0.0022(3) 0.0053(3) O1 0.051(2) 0.0306(17) 0.0214(15) 0.0026(12) 0.0071(14) -0.0007(16) O2 0.098(4) 0.067(3) 0.061(3) -0.012(2) -0.016(3) 0.043(3) N1 0.049(2) 0.054(3) 0.026(2) -0.0188(18) 0.0146(18) -0.024(2) N2 0.043(2) 0.026(2) 0.043(2) 0.0054(17) 0.0096(19) 0.0111(18) N3 0.0347(19) 0.0167(16) 0.0127(15) -0.0005(12) 0.0003(14) 0.0032(15) N4 0.0306(18) 0.0152(16) 0.0173(16) -0.0012(12) 0.0023(14) 0.0014(15) C1 0.038(2) 0.028(2) 0.024(2) -0.0068(17) 0.0056(18) -0.006(2) C2 0.035(2) 0.023(2) 0.019(2) -0.0030(16) 0.0019(17) 0.0006(19) C3 0.041(3) 0.025(2) 0.019(2) -0.0020(16) 0.0118(18) -0.004(2) C4 0.054(3) 0.048(3) 0.023(2) -0.013(2) 0.014(2) -0.023(3) C5 0.037(2) 0.0179(19) 0.0162(19) -0.0041(15) 0.0011(17) 0.0011(18) C6 0.042(3) 0.027(2) 0.020(2) -0.0040(17) 0.0052(18) -0.010(2) C7 0.065(4) 0.066(4) 0.050(4) 0.006(3) -0.003(3) 0.036(4) C8 0.062(3) 0.033(3) 0.026(2) 0.003(2) 0.011(2) 0.021(3) C9 0.038(3) 0.062(3) 0.025(2) -0.004(2) -0.002(2) 0.024(3) C10 0.033(2) 0.037(3) 0.032(2) -0.004(2) -0.0019(19) 0.008(2) C11 0.032(2) 0.021(2) 0.0193(19) -0.0005(15) 0.0015(17) 0.0067(19) C12 0.032(2) 0.024(2) 0.033(2) 0.0004(18) 0.0071(19) 0.006(2) C13 0.036(2) 0.0168(19) 0.0182(19) -0.0003(15) 0.0024(17) 0.0013(18) C14 0.037(2) 0.027(2) 0.020(2) 0.0032(16) -0.0055(18) 0.011(2) C15 0.047(3) 0.026(2) 0.017(2) -0.0006(17) -0.0013(18) 0.009(2) C16 0.037(2) 0.021(2) 0.0158(18) 0.0002(15) -0.0008(16) 0.0026(19) C17 0.034(2) 0.0195(19) 0.0128(17) -0.0034(14) 0.0010(16) -0.0013(18) C18 0.032(2) 0.0169(19) 0.0166(18) -0.0027(14) 0.0018(16) -0.0006(17) C19 0.045(3) 0.023(2) 0.018(2) -0.0045(16) 0.0024(18) 0.008(2) C20 0.040(2) 0.023(2) 0.023(2) -0.0031(17) 0.0040(19) 0.007(2) C21 0.030(2) 0.0167(19) 0.0190(19) -0.0010(15) 0.0053(16) 0.0018(17) C22 0.031(2) 0.0159(19) 0.022(2) 0.0001(15) 0.0023(17) 0.0019(17) 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 _geom_angle_publ_flag N4 Zn1 N4 180.0 . 3_576 ? N4 Zn1 N3 89.57(13) . 3_576 ? N4 Zn1 N3 90.43(13) 3_576 3_576 ? N4 Zn1 N3 90.43(13) . . ? N4 Zn1 N3 89.57(13) 3_576 . ? N3 Zn1 N3 180.0 3_576 . ? N4 Zn1 O1 87.76(12) . 4_576 ? N4 Zn1 O1 92.24(12) 3_576 4_576 ? N3 Zn1 O1 88.44(12) 3_576 4_576 ? N3 Zn1 O1 91.57(12) . 4_576 ? N4 Zn1 O1 92.24(12) . 2 ? N4 Zn1 O1 87.76(12) 3_576 2 ? N3 Zn1 O1 91.56(12) 3_576 2 ? N3 Zn1 O1 88.43(12) . 2 ? O1 Zn1 O1 180.00(13) 4_576 2 ? C1 O1 Zn1 128.9(3) . 2_545 ? C1 O1 H1O1 115.5 . . ? Zn1 O1 H1O1 115.6 2_545 . ? C7 O2 H1O2 107.4 . . ? C4 N1 C2 117.3(4) . . ? C8 N2 C12 117.7(4) . . ? C13 N3 C16 106.7(3) . . ? C13 N3 Zn1 126.8(3) . . ? C16 N3 Zn1 125.7(3) . . ? C21 N4 C18 106.8(3) . . ? C21 N4 Zn1 126.9(3) . . ? C18 N4 Zn1 126.1(3) . . ? O1 C1 C2 111.5(3) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N1 C2 C3 122.5(4) . . ? N1 C2 C1 114.8(4) . . ? C3 C2 C1 122.7(4) . . ? C2 C3 C6 118.5(4) . . ? C2 C3 H3 120.7 . . ? C6 C3 H3 120.7 . . ? N1 C4 C5 124.4(4) . . ? N1 C4 H4 117.8 . . ? C5 C4 H4 117.8 . . ? C6 C5 C4 116.7(4) . . ? C6 C5 C17 122.4(4) . . ? C4 C5 C17 120.9(4) . . ? C5 C6 C3 120.6(4) . . ? C5 C6 H6 119.7 . . ? C3 C6 H6 119.7 . . ? O2 C7 C8 109.6(5) . . ? O2 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O2 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N2 C8 C9 122.5(4) . . ? N2 C8 C7 113.0(5) . . ? C9 C8 C7 124.5(5) . . ? C10 C9 C8 118.4(4) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 116.5(4) . . ? C10 C11 C22 124.4(4) . . ? C12 C11 C22 119.1(4) . . ? N2 C12 C11 125.0(4) . . ? N2 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? N3 C13 C22 124.9(4) . 3_576 ? N3 C13 C14 110.0(3) . . ? C22 C13 C14 125.1(4) 3_576 . ? C15 C14 C13 106.2(4) . . ? C15 C14 H14 126.9 . . ? C13 C14 H14 126.9 . . ? C14 C15 C16 107.7(4) . . ? C14 C15 H15 126.2 . . ? C16 C15 H15 126.2 . . ? N3 C16 C17 125.7(3) . . ? N3 C16 C15 109.4(3) . . ? C17 C16 C15 124.8(4) . . ? C16 C17 C18 126.2(4) . . ? C16 C17 C5 117.6(3) . . ? C18 C17 C5 116.3(4) . . ? N4 C18 C17 125.6(4) . . ? N4 C18 C19 109.5(3) . . ? C17 C18 C19 124.9(4) . . ? C20 C19 C18 107.8(4) . . ? C20 C19 H19 126.1 . . ? C18 C19 H19 126.1 . . ? C19 C20 C21 106.7(4) . . ? C19 C20 H20 126.7 . . ? C21 C20 H20 126.7 . . ? N4 C21 C22 126.0(3) . . ? N4 C21 C20 109.2(3) . . ? C22 C21 C20 124.8(4) . . ? C21 C22 C13 125.3(4) . 3_576 ? C21 C22 C11 115.9(3) . . ? C13 C22 C11 118.8(4) 3_576 . ? 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 Zn1 N4 2.045(3) . ? Zn1 N4 2.045(3) 3_576 ? Zn1 N3 2.068(3) 3_576 ? Zn1 N3 2.068(3) . ? Zn1 O1 2.265(3) 4_576 ? Zn1 O1 2.265(3) 2 ? O1 C1 1.412(5) . ? O1 Zn1 2.265(3) 2_545 ? O1 H1O1 0.9499 . ? O2 C7 1.345(7) . ? O2 H1O2 0.8300 . ? N1 C4 1.339(5) . ? N1 C2 1.345(6) . ? N2 C8 1.324(7) . ? N2 C12 1.327(6) . ? N3 C13 1.365(5) . ? N3 C16 1.370(5) . ? N4 C21 1.360(5) . ? N4 C18 1.379(5) . ? C1 C2 1.517(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.372(6) . ? C3 C6 1.386(5) . ? C3 H3 0.9500 . ? C4 C5 1.383(6) . ? C4 H4 0.9500 . ? C5 C6 1.371(6) . ? C5 C17 1.502(5) . ? C6 H6 0.9500 . ? C7 C8 1.538(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.394(8) . ? C9 C10 1.391(7) . ? C9 H9 0.9500 . ? C10 C11 1.378(6) . ? C10 H10 0.9500 . ? C11 C12 1.389(6) . ? C11 C22 1.491(5) . ? C12 H12 0.9500 . ? C13 C22 1.415(5) 3_576 ? C13 C14 1.445(5) . ? C14 C15 1.356(6) . ? C14 H14 0.9500 . ? C15 C16 1.435(6) . ? C15 H15 0.9500 . ? C16 C17 1.402(5) . ? C17 C18 1.403(5) . ? C18 C19 1.423(6) . ? C19 C20 1.348(6) . ? C19 H19 0.9500 . ? C20 C21 1.455(5) . ? C20 H20 0.9500 . ? C21 C22 1.411(5) . ? C22 C13 1.415(5) 3_576 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O1 N2 0.95 2.01 2.732(5) 131.5 2 O2 H1O2 N1 0.83 2.07 2.900(6) 179.4 4_666