# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_New_Global_Publ_Block _journal_name_full 'Dalton Trans.' #TrackingRef '- 091104Am.cif' # SUBMISSION DETAILS _journal_coden_Cambridge 0222 _publ_contact_author_name 'Guang-Shan Zhu' _publ_contact_author_address ; State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, China ; _publ_contact_author_email zhugs@mail.jlu.edu.cn loop_ _publ_author_name 'Guang-Shan Zhu.' 'Liang Xiao.' data_091104Am _database_code_depnum_ccdc_archive 'CCDC 773973' #TrackingRef '- 091104Am.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 N16 O8 Zn2' _chemical_formula_sum 'C20 H28 N16 O8 Zn2' _chemical_formula_weight 751.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8604(15) _cell_length_b 14.374(2) _cell_length_c 10.3111(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.065(3) _cell_angle_gamma 90.00 _cell_volume 1455.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1639 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 21.55 _exptl_crystal_description diamond-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6440 _exptl_absorpt_correction_T_max 0.7030 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8701 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.53 _reflns_number_total 4762 _reflns_number_gt 4482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.09P)^2^+1.99P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(19) _refine_ls_number_reflns 4762 _refine_ls_number_parameters 419 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 C1 C 0.2980(7) 0.6078(6) 1.0031(7) 0.0306(15) Uani 1 1 d . . . C2 C 0.4281(7) 0.5738(5) 0.9712(7) 0.0318(15) Uani 1 1 d . . . H2A H 0.4876 0.5664 1.0506 0.038 Uiso 1 1 calc R . . H2B H 0.4691 0.6192 0.9171 0.038 Uiso 1 1 calc R . . C3 C 0.4160(7) 0.4830(5) 0.9010(7) 0.0337(16) Uani 1 1 d . . . C4 C 0.5432(9) 0.3866(6) 0.7690(8) 0.044(2) Uani 1 1 d . . . H4A H 0.5997 0.4047 0.7008 0.052 Uiso 1 1 calc R . . H4B H 0.4527 0.3727 0.7290 0.052 Uiso 1 1 calc R . . C5 C 0.6026(8) 0.3012(6) 0.8386(7) 0.0356(16) Uani 1 1 d . . . H5A H 0.6907 0.3159 0.8808 0.053 Uiso 1 1 calc R . . H5B H 0.6112 0.2522 0.7767 0.053 Uiso 1 1 calc R . . H5C H 0.5436 0.2814 0.9026 0.053 Uiso 1 1 calc R . . C6 C 0.4368(7) 0.8939(6) 0.7178(6) 0.0313(16) Uani 1 1 d . . . C7 C 0.3558(7) 0.9568(5) 0.6278(7) 0.0325(16) Uani 1 1 d . . . H7A H 0.2600 0.9462 0.6375 0.039 Uiso 1 1 calc R . . H7B H 0.3719 0.9402 0.5393 0.039 Uiso 1 1 calc R . . C8 C 0.3847(7) 1.0592(6) 0.6465(7) 0.0328(16) Uani 1 1 d . . . C9 C 0.3094(8) 1.2100(6) 0.5893(7) 0.0396(18) Uani 1 1 d . . . H9A H 0.3310 1.2270 0.6798 0.047 Uiso 1 1 calc R . . H9B H 0.2235 1.2392 0.5594 0.047 Uiso 1 1 calc R . . C10 C 0.4193(7) 1.2450(6) 0.5098(7) 0.0367(16) Uani 1 1 d . . . H10A H 0.5066 1.2352 0.5568 0.055 Uiso 1 1 calc R . . H10B H 0.4063 1.3103 0.4932 0.055 Uiso 1 1 calc R . . H10C H 0.4153 1.2120 0.4287 0.055 Uiso 1 1 calc R . . C11 C -0.0091(7) 0.8815(5) 0.7994(7) 0.0313(15) Uani 1 1 d . . . C12 C 0.0332(7) 0.9135(6) 0.9310(7) 0.0326(15) Uani 1 1 d . . . H12A H 0.0775 0.8622 0.9789 0.039 Uiso 1 1 calc R . . H12B H -0.0477 0.9292 0.9734 0.039 Uiso 1 1 calc R . . C13 C 0.1272(7) 0.9954(6) 0.9412(8) 0.0400(18) Uani 1 1 d . . . C14 C 0.2087(8) 1.1179(7) 1.0801(8) 0.044(2) Uani 1 1 d . . . H14A H 0.1709 1.1702 1.0297 0.053 Uiso 1 1 calc R . . H14B H 0.3013 1.1073 1.0585 0.053 Uiso 1 1 calc R . . C15 C 0.2054(8) 1.1358(6) 1.2239(8) 0.043(2) Uani 1 1 d . . . H15A H 0.1127 1.1366 1.2454 0.064 Uiso 1 1 calc R . . H15B H 0.2472 1.1947 1.2456 0.064 Uiso 1 1 calc R . . H15C H 0.2542 1.0873 1.2722 0.064 Uiso 1 1 calc R . . C16 C -0.2028(6) 1.1214(5) 0.5005(7) 0.0312(16) Uani 1 1 d . . . C17 C -0.0806(7) 1.1613(5) 0.5753(7) 0.0345(17) Uani 1 1 d . . . H17A H -0.0590 1.1242 0.6530 0.041 Uiso 1 1 calc R . . H17B H -0.0039 1.1576 0.5228 0.041 Uiso 1 1 calc R . . C18 C -0.0993(7) 1.2586(6) 0.6137(7) 0.0361(18) Uani 1 1 d . . . C19 C 0.0130(9) 1.3780(7) 0.7447(9) 0.045(2) Uani 1 1 d . . . H19A H 0.0848 1.3779 0.8154 0.054 Uiso 1 1 calc R . . H19B H -0.0727 1.3877 0.7821 0.054 Uiso 1 1 calc R . . C20 C 0.0364(9) 1.4567(7) 0.6551(9) 0.049(2) Uani 1 1 d . . . H20A H 0.1123 1.4425 0.6063 0.073 Uiso 1 1 calc R . . H20B H 0.0554 1.5123 0.7049 0.073 Uiso 1 1 calc R . . H20C H -0.0436 1.4659 0.5963 0.073 Uiso 1 1 calc R . . N1 N 0.2188(6) 0.6691(5) 0.9351(6) 0.0309(13) Uani 1 1 d . . . N2 N 0.1087(5) 0.6855(4) 1.0031(5) 0.0282(12) Uani 1 1 d . . . N3 N 0.1212(6) 0.6368(5) 1.1092(6) 0.0321(13) Uani 1 1 d . . . N4 N 0.2370(6) 0.5884(5) 1.1149(7) 0.0387(15) Uani 1 1 d . . . N5 N 0.3944(7) 0.8152(5) 0.7716(6) 0.0376(15) Uani 1 1 d . . . N6 N 0.5009(6) 0.7790(4) 0.8441(6) 0.0355(14) Uani 1 1 d . . . N7 N 0.6056(6) 0.8330(5) 0.8351(6) 0.0345(14) Uani 1 1 d . . . N8 N 0.5689(6) 0.9054(5) 0.7578(5) 0.0283(13) Uani 1 1 d . . . N9 N 0.0520(7) 0.8148(5) 0.7345(7) 0.0376(15) Uani 1 1 d . . . N10 N -0.0219(6) 0.8063(5) 0.6189(6) 0.0346(14) Uani 1 1 d . . . N11 N -0.1249(7) 0.8639(5) 0.6139(6) 0.0415(16) Uani 1 1 d . . . N12 N -0.1203(6) 0.9109(5) 0.7274(6) 0.0352(14) Uani 1 1 d . . . N13 N -0.2850(6) 1.0603(5) 0.5540(6) 0.0350(14) Uani 1 1 d . . . N14 N -0.3871(6) 1.0411(4) 0.4584(6) 0.0341(14) Uani 1 1 d . . . N15 N -0.3651(6) 1.0900(4) 0.3557(6) 0.0341(14) Uani 1 1 d . . . N16 N -0.2506(6) 1.1414(5) 0.3808(6) 0.0342(14) Uani 1 1 d . . . O1 O 0.5364(6) 0.4611(4) 0.8599(5) 0.0445(14) Uani 1 1 d . . . O2 O 0.3137(6) 0.4409(4) 0.8790(5) 0.0426(13) Uani 1 1 d . . . O3 O 0.4758(5) 1.0891(4) 0.7175(5) 0.0360(12) Uani 1 1 d . . . O4 O 0.2954(5) 1.1078(4) 0.5787(5) 0.0393(13) Uani 1 1 d . . . O5 O 0.1932(5) 1.0212(4) 0.8554(5) 0.0424(14) Uani 1 1 d . . . O6 O 0.1262(6) 1.0353(4) 1.0548(5) 0.0460(14) Uani 1 1 d . . . O7 O 0.0100(5) 1.2912(4) 0.6833(5) 0.0453(15) Uani 1 1 d . . . O8 O -0.2020(6) 1.3030(4) 0.5871(5) 0.0449(14) Uani 1 1 d . . . Zn1 Zn 0.22262(7) 0.73722(5) 0.76086(7) 0.0276(2) Uani 1 1 d . . . Zn2 Zn -0.28632(7) 1.00192(6) 0.73237(7) 0.0303(2) 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 0.025(3) 0.033(4) 0.036(3) 0.001(3) 0.010(3) -0.001(3) C2 0.034(4) 0.029(4) 0.034(3) 0.007(3) 0.010(3) 0.007(3) C3 0.031(3) 0.022(4) 0.046(4) -0.007(3) -0.003(3) 0.010(3) C4 0.040(4) 0.040(5) 0.048(4) -0.019(4) -0.015(3) 0.017(4) C5 0.043(4) 0.035(4) 0.027(3) 0.002(3) -0.008(3) 0.005(3) C6 0.023(3) 0.043(5) 0.028(3) -0.009(3) 0.003(3) -0.004(3) C7 0.029(3) 0.026(4) 0.041(4) 0.000(3) -0.005(3) 0.003(3) C8 0.026(3) 0.036(4) 0.037(4) 0.000(3) 0.007(3) -0.001(3) C9 0.046(4) 0.036(5) 0.036(4) 0.018(3) 0.000(3) 0.003(3) C10 0.031(3) 0.039(5) 0.040(3) 0.017(4) 0.005(3) 0.000(3) C11 0.036(4) 0.027(4) 0.033(3) 0.005(3) 0.012(3) -0.007(3) C12 0.028(3) 0.033(4) 0.035(4) -0.002(3) -0.004(3) 0.004(3) C13 0.027(3) 0.037(5) 0.058(4) -0.023(4) 0.010(3) 0.005(3) C14 0.039(4) 0.045(5) 0.050(5) -0.012(4) 0.011(3) -0.019(4) C15 0.043(4) 0.042(5) 0.044(4) -0.020(4) 0.013(3) -0.024(3) C16 0.020(3) 0.034(4) 0.040(4) 0.002(3) 0.000(3) 0.000(3) C17 0.034(4) 0.029(4) 0.040(4) 0.012(3) 0.002(3) -0.012(3) C18 0.034(4) 0.044(5) 0.033(3) -0.008(3) 0.018(3) -0.023(3) C19 0.048(5) 0.047(6) 0.044(4) -0.015(4) 0.021(4) -0.024(4) C20 0.043(4) 0.055(6) 0.052(5) -0.021(4) 0.023(4) -0.015(4) N1 0.028(3) 0.023(3) 0.042(3) 0.005(3) 0.006(2) -0.001(2) N2 0.029(3) 0.026(3) 0.030(3) 0.010(2) 0.005(2) -0.004(2) N3 0.035(3) 0.032(4) 0.031(3) 0.006(2) 0.010(2) 0.007(3) N4 0.030(3) 0.036(4) 0.050(4) 0.009(3) 0.006(3) 0.002(3) N5 0.036(3) 0.036(4) 0.040(3) 0.009(3) -0.003(3) -0.007(3) N6 0.038(3) 0.025(3) 0.043(3) 0.017(3) 0.004(3) -0.008(3) N7 0.031(3) 0.034(4) 0.039(3) 0.004(3) 0.011(2) -0.001(3) N8 0.027(3) 0.031(3) 0.027(3) 0.006(2) 0.004(2) 0.003(2) N9 0.047(4) 0.020(4) 0.046(3) -0.010(3) 0.000(3) 0.002(3) N10 0.032(3) 0.026(3) 0.046(3) 0.001(3) 0.005(3) 0.015(3) N11 0.035(3) 0.046(4) 0.042(3) -0.007(3) -0.007(3) 0.015(3) N12 0.028(3) 0.033(4) 0.043(3) -0.015(3) -0.002(2) 0.004(3) N13 0.028(3) 0.033(4) 0.044(3) 0.006(3) 0.003(2) 0.002(3) N14 0.025(3) 0.027(3) 0.049(3) 0.003(3) -0.005(2) -0.014(2) N15 0.040(3) 0.023(3) 0.040(3) 0.004(3) 0.011(3) -0.004(3) N16 0.030(3) 0.031(3) 0.041(3) -0.006(3) 0.001(2) -0.003(2) O1 0.047(3) 0.046(4) 0.038(3) -0.015(2) -0.011(2) 0.014(3) O2 0.048(3) 0.039(3) 0.039(3) -0.012(2) -0.006(2) -0.010(3) O3 0.036(3) 0.033(3) 0.039(3) 0.004(2) 0.003(2) -0.006(2) O4 0.033(3) 0.037(3) 0.046(3) 0.013(2) -0.006(2) 0.001(2) O5 0.047(3) 0.043(4) 0.040(3) -0.018(2) 0.017(2) -0.014(2) O6 0.043(3) 0.051(4) 0.044(3) -0.016(3) 0.005(2) -0.009(3) O7 0.043(3) 0.052(4) 0.042(3) -0.021(3) 0.014(2) -0.017(3) O8 0.055(3) 0.039(3) 0.044(3) -0.015(2) 0.018(3) -0.007(3) Zn1 0.0278(4) 0.0267(4) 0.0285(3) 0.0006(3) 0.0039(3) 0.0001(3) Zn2 0.0287(4) 0.0351(5) 0.0276(3) -0.0007(4) 0.0041(3) -0.0025(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.335(10) . ? C1 N4 1.375(10) . ? C1 C2 1.438(9) . ? C2 C3 1.493(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O2 1.180(9) . ? C3 O1 1.333(9) . ? C4 O1 1.429(9) . ? C4 C5 1.513(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N8 1.341(9) . ? C6 N5 1.342(11) . ? C6 C7 1.479(10) . ? C7 C8 1.508(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O3 1.188(9) . ? C8 O4 1.282(9) . ? C9 O4 1.479(10) . ? C9 C10 1.503(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N12 1.337(10) . ? C11 N9 1.343(10) . ? C11 C12 1.458(10) . ? C12 C13 1.496(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O5 1.202(10) . ? C13 O6 1.306(9) . ? C14 O6 1.450(10) . ? C14 C15 1.508(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N16 1.313(9) . ? C16 N13 1.346(10) . ? C16 C17 1.487(10) . ? C17 C18 1.470(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 O8 1.208(10) . ? C18 O7 1.326(9) . ? C19 O7 1.398(11) . ? C19 C20 1.491(14) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 N2 1.363(8) . ? N1 Zn1 2.049(6) . ? N2 N3 1.296(8) . ? N3 N4 1.334(9) . ? N4 Zn2 2.031(7) 2_547 ? N5 N6 1.338(9) . ? N5 Zn1 2.026(6) . ? N6 N7 1.301(9) . ? N7 N8 1.341(9) . ? N8 Zn2 2.024(6) 1_655 ? N9 N10 1.347(9) . ? N9 Zn1 2.016(7) . ? N10 N11 1.307(9) . ? N11 N12 1.349(9) . ? N12 Zn2 2.099(6) . ? N13 N14 1.373(8) . ? N13 Zn2 2.023(6) . ? N14 N15 1.305(9) . ? N15 N16 1.355(9) . ? N16 Zn1 2.044(7) 2_556 ? Zn1 N16 2.044(7) 2_546 ? Zn2 N8 2.024(6) 1_455 ? Zn2 N4 2.031(7) 2_557 ? 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 N1 C1 N4 107.2(6) . . ? N1 C1 C2 126.6(7) . . ? N4 C1 C2 126.1(7) . . ? C1 C2 C3 111.9(6) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O2 C3 O1 126.0(7) . . ? O2 C3 C2 124.9(6) . . ? O1 C3 C2 109.0(6) . . ? O1 C4 C5 109.5(6) . . ? O1 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? O1 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N8 C6 N5 107.9(6) . . ? N8 C6 C7 125.0(7) . . ? N5 C6 C7 127.2(6) . . ? C6 C7 C8 115.5(6) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? O3 C8 O4 125.8(8) . . ? O3 C8 C7 123.8(7) . . ? O4 C8 C7 110.4(6) . . ? O4 C9 C10 111.0(7) . . ? O4 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? O4 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N12 C11 N9 109.3(6) . . ? N12 C11 C12 124.8(7) . . ? N9 C11 C12 125.8(7) . . ? C11 C12 C13 116.0(7) . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? O5 C13 O6 124.9(8) . . ? O5 C13 C12 124.3(7) . . ? O6 C13 C12 110.8(7) . . ? O6 C14 C15 104.8(7) . . ? O6 C14 H14A 110.8 . . ? C15 C14 H14A 110.8 . . ? O6 C14 H14B 110.8 . . ? C15 C14 H14B 110.8 . . ? H14A C14 H14B 108.9 . . ? 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 . . ? N16 C16 N13 110.4(6) . . ? N16 C16 C17 127.6(7) . . ? N13 C16 C17 121.9(6) . . ? C18 C17 C16 113.1(7) . . ? C18 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? O8 C18 O7 124.2(8) . . ? O8 C18 C17 124.3(7) . . ? O7 C18 C17 111.5(7) . . ? O7 C19 C20 113.2(7) . . ? O7 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? O7 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 N2 107.4(6) . . ? C1 N1 Zn1 136.1(5) . . ? N2 N1 Zn1 116.5(4) . . ? N3 N2 N1 108.7(6) . . ? N2 N3 N4 109.6(6) . . ? N3 N4 C1 107.1(6) . . ? N3 N4 Zn2 119.9(5) . 2_547 ? C1 N4 Zn2 132.9(5) . 2_547 ? N6 N5 C6 107.5(6) . . ? N6 N5 Zn1 115.2(5) . . ? C6 N5 Zn1 137.1(5) . . ? N7 N6 N5 108.5(6) . . ? N6 N7 N8 109.3(6) . . ? N7 N8 C6 106.9(6) . . ? N7 N8 Zn2 116.9(4) . 1_655 ? C6 N8 Zn2 136.2(5) . 1_655 ? C11 N9 N10 105.9(6) . . ? C11 N9 Zn1 137.2(5) . . ? N10 N9 Zn1 116.7(5) . . ? N11 N10 N9 109.6(6) . . ? N10 N11 N12 108.4(6) . . ? C11 N12 N11 106.6(6) . . ? C11 N12 Zn2 141.8(5) . . ? N11 N12 Zn2 111.5(4) . . ? C16 N13 N14 105.5(6) . . ? C16 N13 Zn2 134.1(5) . . ? N14 N13 Zn2 120.4(5) . . ? N15 N14 N13 108.1(5) . . ? N14 N15 N16 109.5(6) . . ? C16 N16 N15 106.5(6) . . ? C16 N16 Zn1 139.4(5) . 2_556 ? N15 N16 Zn1 113.2(5) . 2_556 ? C3 O1 C4 118.7(6) . . ? C8 O4 C9 116.5(6) . . ? C13 O6 C14 118.2(6) . . ? C18 O7 C19 122.9(7) . . ? N9 Zn1 N5 112.7(3) . . ? N9 Zn1 N16 116.1(3) . 2_546 ? N5 Zn1 N16 104.3(3) . 2_546 ? N9 Zn1 N1 107.6(3) . . ? N5 Zn1 N1 107.2(2) . . ? N16 Zn1 N1 108.6(3) 2_546 . ? N13 Zn2 N8 117.6(2) . 1_455 ? N13 Zn2 N4 115.5(3) . 2_557 ? N8 Zn2 N4 116.3(3) 1_455 2_557 ? N13 Zn2 N12 99.7(3) . . ? N8 Zn2 N12 97.8(3) 1_455 . ? N4 Zn2 N12 105.4(3) 2_557 . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -96.4(9) . . . . ? N4 C1 C2 C3 89.1(9) . . . . ? C1 C2 C3 O2 -3.4(11) . . . . ? C1 C2 C3 O1 172.3(6) . . . . ? N8 C6 C7 C8 -39.0(10) . . . . ? N5 C6 C7 C8 142.6(8) . . . . ? C6 C7 C8 O3 8.3(11) . . . . ? C6 C7 C8 O4 -169.8(6) . . . . ? N12 C11 C12 C13 -91.0(9) . . . . ? N9 C11 C12 C13 93.0(9) . . . . ? C11 C12 C13 O5 -18.4(11) . . . . ? C11 C12 C13 O6 160.8(7) . . . . ? N16 C16 C17 C18 71.0(10) . . . . ? N13 C16 C17 C18 -105.5(8) . . . . ? C16 C17 C18 O8 -0.6(10) . . . . ? C16 C17 C18 O7 178.2(6) . . . . ? N4 C1 N1 N2 -1.5(9) . . . . ? C2 C1 N1 N2 -176.9(7) . . . . ? N4 C1 N1 Zn1 -179.6(5) . . . . ? C2 C1 N1 Zn1 5.0(13) . . . . ? C1 N1 N2 N3 0.8(8) . . . . ? Zn1 N1 N2 N3 179.3(5) . . . . ? N1 N2 N3 N4 0.3(8) . . . . ? N2 N3 N4 C1 -1.2(8) . . . . ? N2 N3 N4 Zn2 -178.6(5) . . . 2_547 ? N1 C1 N4 N3 1.6(9) . . . . ? C2 C1 N4 N3 177.1(7) . . . . ? N1 C1 N4 Zn2 178.5(5) . . . 2_547 ? C2 C1 N4 Zn2 -6.0(13) . . . 2_547 ? N8 C6 N5 N6 -0.1(8) . . . . ? C7 C6 N5 N6 178.6(7) . . . . ? N8 C6 N5 Zn1 -174.9(6) . . . . ? C7 C6 N5 Zn1 3.8(13) . . . . ? C6 N5 N6 N7 -0.3(8) . . . . ? Zn1 N5 N6 N7 175.8(5) . . . . ? N5 N6 N7 N8 0.6(8) . . . . ? N6 N7 N8 C6 -0.6(8) . . . . ? N6 N7 N8 Zn2 178.3(5) . . . 1_655 ? N5 C6 N8 N7 0.4(8) . . . . ? C7 C6 N8 N7 -178.3(7) . . . . ? N5 C6 N8 Zn2 -178.2(5) . . . 1_655 ? C7 C6 N8 Zn2 3.1(11) . . . 1_655 ? N12 C11 N9 N10 2.1(9) . . . . ? C12 C11 N9 N10 178.6(7) . . . . ? N12 C11 N9 Zn1 176.6(6) . . . . ? C12 C11 N9 Zn1 -7.0(13) . . . . ? C11 N9 N10 N11 -1.1(9) . . . . ? Zn1 N9 N10 N11 -176.9(5) . . . . ? N9 N10 N11 N12 -0.3(9) . . . . ? N9 C11 N12 N11 -2.3(9) . . . . ? C12 C11 N12 N11 -178.8(7) . . . . ? N9 C11 N12 Zn2 176.8(7) . . . . ? C12 C11 N12 Zn2 0.3(14) . . . . ? N10 N11 N12 C11 1.6(9) . . . . ? N10 N11 N12 Zn2 -177.8(5) . . . . ? N16 C16 N13 N14 1.4(9) . . . . ? C17 C16 N13 N14 178.4(7) . . . . ? N16 C16 N13 Zn2 -176.6(5) . . . . ? C17 C16 N13 Zn2 0.4(12) . . . . ? C16 N13 N14 N15 -0.8(8) . . . . ? Zn2 N13 N14 N15 177.5(5) . . . . ? N13 N14 N15 N16 0.0(8) . . . . ? N13 C16 N16 N15 -1.4(9) . . . . ? C17 C16 N16 N15 -178.2(7) . . . . ? N13 C16 N16 Zn1 166.0(6) . . . 2_556 ? C17 C16 N16 Zn1 -10.8(13) . . . 2_556 ? N14 N15 N16 C16 0.9(8) . . . . ? N14 N15 N16 Zn1 -170.2(5) . . . 2_556 ? O2 C3 O1 C4 7.7(12) . . . . ? C2 C3 O1 C4 -168.0(7) . . . . ? C5 C4 O1 C3 -103.9(8) . . . . ? O3 C8 O4 C9 0.9(11) . . . . ? C7 C8 O4 C9 178.9(6) . . . . ? C10 C9 O4 C8 78.0(8) . . . . ? O5 C13 O6 C14 1.0(12) . . . . ? C12 C13 O6 C14 -178.2(7) . . . . ? C15 C14 O6 C13 -170.0(7) . . . . ? O8 C18 O7 C19 6.6(11) . . . . ? C17 C18 O7 C19 -172.3(7) . . . . ? C20 C19 O7 C18 -81.0(9) . . . . ? C11 N9 Zn1 N5 -61.9(9) . . . . ? N10 N9 Zn1 N5 112.1(6) . . . . ? C11 N9 Zn1 N16 177.9(8) . . . 2_546 ? N10 N9 Zn1 N16 -8.1(7) . . . 2_546 ? C11 N9 Zn1 N1 56.0(9) . . . . ? N10 N9 Zn1 N1 -129.9(6) . . . . ? N6 N5 Zn1 N9 150.9(5) . . . . ? C6 N5 Zn1 N9 -34.5(9) . . . . ? N6 N5 Zn1 N16 -82.3(6) . . . 2_546 ? C6 N5 Zn1 N16 92.2(8) . . . 2_546 ? N6 N5 Zn1 N1 32.7(6) . . . . ? C6 N5 Zn1 N1 -152.8(8) . . . . ? C1 N1 Zn1 N9 177.9(8) . . . . ? N2 N1 Zn1 N9 -0.1(6) . . . . ? C1 N1 Zn1 N5 -60.7(8) . . . . ? N2 N1 Zn1 N5 121.3(5) . . . . ? C1 N1 Zn1 N16 51.5(8) . . . 2_546 ? N2 N1 Zn1 N16 -126.5(5) . . . 2_546 ? C16 N13 Zn2 N8 -176.1(7) . . . 1_455 ? N14 N13 Zn2 N8 6.1(7) . . . 1_455 ? C16 N13 Zn2 N4 40.5(8) . . . 2_557 ? N14 N13 Zn2 N4 -137.2(5) . . . 2_557 ? C16 N13 Zn2 N12 -71.9(8) . . . . ? N14 N13 Zn2 N12 110.4(6) . . . . ? C11 N12 Zn2 N13 135.2(9) . . . . ? N11 N12 Zn2 N13 -45.7(6) . . . . ? C11 N12 Zn2 N8 -104.9(9) . . . 1_455 ? N11 N12 Zn2 N8 74.2(6) . . . 1_455 ? C11 N12 Zn2 N4 15.2(10) . . . 2_557 ? N11 N12 Zn2 N4 -165.7(6) . . . 2_557 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.415 _refine_diff_density_min -0.855 _refine_diff_density_rms 0.096