# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Jian-Fang Ma' _publ_contact_author_address ; Department of Chemistry Northeast Normal University Changchun 130024 P.R.China ; _publ_contact_author_email jianfangma@yahoo.com.cn _publ_contact_author_fax +86-431-85098620 _publ_contact_author_phone +86-431-85098620 _publ_author_name 'Jian-Fang Ma' #=========================================================== data_compound-1 _database_code_depnum_ccdc_archive 'CCDC 892065' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H18 N8 O5 Zn' _chemical_formula_sum 'C23 H18 N8 O5 Zn' _chemical_formula_weight 551.82 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 triclinic _symmetry_space_group_name_H-M p-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9771(6) _cell_length_b 11.0283(7) _cell_length_c 12.0901(6) _cell_angle_alpha 74.718(5) _cell_angle_beta 85.000(5) _cell_angle_gamma 81.608(6) _cell_volume 1140.77(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2664 _cell_measurement_theta_min 2.7991 _cell_measurement_theta_max 29.1911 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7651 _exptl_absorpt_correction_T_max 0.8053 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7062 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4154 _reflns_number_gt 3394 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0316P)^2^+0.2850P] 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_number_reflns 4154 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _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 Zn1 Zn 0.27480(4) 0.42344(3) 0.12097(3) 0.02937(13) Uani 1 1 d . . . C1 C 0.0527(4) 0.3976(3) 0.3401(2) 0.0373(8) Uani 1 1 d . . . H1 H 0.1186 0.4252 0.3806 0.045 Uiso 1 1 calc R . . C2 C -0.0393(4) 0.3523(3) 0.2045(2) 0.0316(7) Uani 1 1 d . . . H2 H -0.0561 0.3398 0.1337 0.038 Uiso 1 1 calc R . . C3 C -0.2743(3) 0.2780(3) 0.3072(3) 0.0344(7) Uani 1 1 d . . . H3A H -0.2974 0.2696 0.2329 0.041 Uiso 1 1 calc R . . H3B H -0.3540 0.3366 0.3312 0.041 Uiso 1 1 calc R . . C4 C -0.3245(4) 0.0239(3) 0.5427(2) 0.0315(7) Uani 1 1 d . . . C5 C -0.3906(3) -0.0357(3) 0.6571(2) 0.0303(7) Uani 1 1 d . . . C6 C -0.4965(4) 0.0254(3) 0.7188(3) 0.0436(9) Uani 1 1 d . . . H6 H -0.5359 0.1093 0.6884 0.052 Uiso 1 1 calc R . . C7 C -0.5443(4) -0.0400(3) 0.8276(3) 0.0488(10) Uani 1 1 d . . . H7 H -0.6164 -0.0006 0.8712 0.059 Uiso 1 1 calc R . . C8 C -0.4833(4) -0.1644(3) 0.8700(3) 0.0415(8) Uani 1 1 d . . . H8 H -0.5162 -0.2076 0.9428 0.050 Uiso 1 1 calc R . . C9 C -0.3360(4) -0.1609(3) 0.7065(2) 0.0352(7) Uani 1 1 d . . . H9 H -0.2648 -0.2024 0.6640 0.042 Uiso 1 1 calc R . . C10 C -0.1840(4) 0.0422(3) 0.3924(2) 0.0311(7) Uani 1 1 d . . . C11 C -0.0694(4) 0.0127(3) 0.3058(3) 0.0344(7) Uani 1 1 d . . . C12 C 0.0368(4) -0.0931(3) 0.3356(3) 0.0403(8) Uani 1 1 d . . . H12 H 0.0374 -0.1441 0.4103 0.048 Uiso 1 1 calc R . . C13 C 0.1408(4) -0.1216(3) 0.2537(3) 0.0529(10) Uani 1 1 d . . . H13 H 0.2123 -0.1929 0.2713 0.063 Uiso 1 1 calc R . . C14 C 0.1373(5) -0.0426(4) 0.1448(3) 0.0578(11) Uani 1 1 d . . . H14 H 0.2072 -0.0590 0.0874 0.069 Uiso 1 1 calc R . . C15 C 0.0287(5) 0.0612(3) 0.1222(3) 0.0566(11) Uani 1 1 d . . . H15 H 0.0277 0.1141 0.0482 0.068 Uiso 1 1 calc R . . C16 C 0.2563(4) 0.3702(3) -0.0814(2) 0.0303(7) Uani 1 1 d . . . C17 C 0.5625(3) 0.4040(3) -0.1967(2) 0.0282(7) Uani 1 1 d . . . C18 C 0.4330(3) 0.3849(2) -0.2582(2) 0.0259(6) Uani 1 1 d . . . C19 C 0.2924(3) 0.3599(2) -0.2032(2) 0.0283(7) Uani 1 1 d . . . C20 C 0.1857(4) 0.3277(3) -0.2624(3) 0.0373(8) Uani 1 1 d . . . H20 H 0.0936 0.3085 -0.2255 0.045 Uiso 1 1 calc R . . C21 C 0.2138(4) 0.3237(3) -0.3757(3) 0.0410(8) Uani 1 1 d . . . H21 H 0.1409 0.3018 -0.4144 0.049 Uiso 1 1 calc R . . C22 C 0.3493(4) 0.3522(3) -0.4313(3) 0.0395(8) Uani 1 1 d . . . H22 H 0.3675 0.3516 -0.5081 0.047 Uiso 1 1 calc R . . C23 C 0.4580(4) 0.3818(3) -0.3727(2) 0.0336(7) Uani 1 1 d . . . H23 H 0.5500 0.3999 -0.4103 0.040 Uiso 1 1 calc R . . N1 N 0.0796(3) 0.3958(2) 0.22734(19) 0.0320(6) Uani 1 1 d . . . N2 N -0.0749(3) 0.3568(2) 0.3860(2) 0.0383(7) Uani 1 1 d . . . N3 N -0.1322(3) 0.3284(2) 0.29695(19) 0.0290(6) Uani 1 1 d . . . N4 N -0.2690(3) 0.1546(2) 0.3904(2) 0.0316(6) Uani 1 1 d . . . N5 N -0.3605(3) 0.1440(2) 0.4879(2) 0.0337(6) Uani 1 1 d . . . N6 N -0.2165(3) -0.0423(2) 0.4887(2) 0.0334(6) Uani 1 1 d . . . N7 N -0.3792(3) -0.2255(2) 0.8114(2) 0.0337(6) Uani 1 1 d . . . N8 N -0.0755(3) 0.0908(2) 0.1999(2) 0.0455(7) Uani 1 1 d . . . O1 O 0.3505(3) 0.41392(19) -0.03641(16) 0.0368(5) Uani 1 1 d . . . O2 O 0.1353(3) 0.3384(2) -0.03135(17) 0.0504(6) Uani 1 1 d . . . O3 O 0.5923(2) 0.51696(17) -0.21468(16) 0.0336(5) Uani 1 1 d . . . O4 O 0.6351(3) 0.30686(18) -0.13879(18) 0.0398(5) Uani 1 1 d . . . O1W O 0.1673(2) 0.61286(18) 0.04021(16) 0.0394(5) Uani 1 1 d . . . H1A H 0.0728 0.6300 0.0564 0.059 Uiso 1 1 d R . . H1B H 0.2231 0.6508 0.0707 0.059 Uiso 1 1 d 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 Zn1 0.0288(2) 0.0354(2) 0.02439(19) -0.00570(14) 0.00082(14) -0.01044(15) C1 0.039(2) 0.0447(18) 0.0305(16) -0.0089(14) -0.0052(15) -0.0117(16) C2 0.037(2) 0.0320(15) 0.0245(15) -0.0033(13) 0.0004(14) -0.0094(14) C3 0.0239(18) 0.0310(15) 0.0401(17) 0.0060(13) -0.0030(14) -0.0038(13) C4 0.0297(19) 0.0293(15) 0.0339(16) -0.0047(13) 0.0015(14) -0.0062(13) C5 0.0291(18) 0.0309(15) 0.0307(15) -0.0054(13) 0.0013(13) -0.0092(13) C6 0.043(2) 0.0346(17) 0.0454(18) -0.0010(15) 0.0053(17) -0.0012(15) C7 0.046(2) 0.047(2) 0.0435(19) -0.0050(16) 0.0148(17) 0.0022(17) C8 0.039(2) 0.0461(19) 0.0333(17) 0.0000(15) 0.0052(15) -0.0088(16) C9 0.040(2) 0.0328(16) 0.0322(16) -0.0076(13) 0.0010(14) -0.0067(14) C10 0.0308(19) 0.0314(16) 0.0320(16) -0.0083(13) -0.0014(14) -0.0069(14) C11 0.033(2) 0.0358(16) 0.0365(17) -0.0109(14) 0.0026(14) -0.0118(14) C12 0.035(2) 0.0413(18) 0.0453(18) -0.0137(15) 0.0017(16) -0.0055(15) C13 0.043(2) 0.055(2) 0.066(2) -0.029(2) 0.0046(19) -0.0009(18) C14 0.056(3) 0.066(2) 0.058(2) -0.031(2) 0.022(2) -0.014(2) C15 0.072(3) 0.059(2) 0.0392(19) -0.0135(18) 0.016(2) -0.019(2) C16 0.0258(18) 0.0337(16) 0.0269(15) -0.0028(13) -0.0028(13) 0.0020(13) C17 0.0268(17) 0.0324(16) 0.0259(14) -0.0101(13) 0.0044(13) -0.0041(13) C18 0.0300(18) 0.0208(13) 0.0268(14) -0.0052(11) -0.0042(13) -0.0025(12) C19 0.0284(18) 0.0283(14) 0.0266(14) -0.0029(12) -0.0029(13) -0.0047(13) C20 0.0322(19) 0.0427(17) 0.0373(17) -0.0059(14) -0.0034(14) -0.0130(15) C21 0.045(2) 0.0445(18) 0.0378(18) -0.0104(15) -0.0149(16) -0.0124(16) C22 0.052(2) 0.0405(17) 0.0271(16) -0.0114(14) -0.0056(15) -0.0036(16) C23 0.035(2) 0.0364(16) 0.0280(15) -0.0063(13) 0.0031(14) -0.0072(14) N1 0.0316(16) 0.0372(14) 0.0260(13) -0.0042(11) 0.0010(11) -0.0097(12) N2 0.0425(18) 0.0413(14) 0.0288(13) -0.0051(12) 0.0011(12) -0.0068(13) N3 0.0288(15) 0.0294(12) 0.0257(12) -0.0005(10) 0.0005(11) -0.0063(11) N4 0.0288(15) 0.0286(13) 0.0327(13) -0.0014(11) 0.0048(11) -0.0043(11) N5 0.0290(15) 0.0307(13) 0.0373(14) -0.0028(11) 0.0063(12) -0.0061(11) N6 0.0335(16) 0.0291(12) 0.0347(13) -0.0041(11) 0.0029(12) -0.0052(11) N7 0.0383(17) 0.0321(13) 0.0287(13) -0.0022(11) 0.0008(12) -0.0101(12) N8 0.053(2) 0.0466(16) 0.0349(15) -0.0084(13) 0.0077(14) -0.0077(14) O1 0.0375(14) 0.0487(12) 0.0256(10) -0.0107(10) -0.0019(10) -0.0078(11) O2 0.0304(14) 0.0834(17) 0.0336(12) -0.0073(12) 0.0069(10) -0.0144(12) O3 0.0371(14) 0.0325(11) 0.0333(11) -0.0051(9) -0.0097(10) -0.0123(10) O4 0.0343(14) 0.0332(11) 0.0509(13) -0.0094(10) -0.0142(11) 0.0034(10) O1W 0.0302(13) 0.0467(12) 0.0402(12) -0.0065(10) -0.0088(10) -0.0055(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O1 1.9880(19) . ? Zn1 O3 1.999(2) 2_665 ? Zn1 N1 2.091(2) . ? Zn1 O1W 2.179(2) . ? Zn1 N7 2.215(2) 2_556 ? C1 N2 1.315(4) . ? C1 N1 1.368(4) . ? C1 H1 0.9300 . ? C2 N1 1.310(4) . ? C2 N3 1.327(3) . ? C2 H2 0.9300 . ? C3 N3 1.447(4) . ? C3 N4 1.461(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N5 1.322(3) . ? C4 N6 1.355(4) . ? C4 C5 1.480(4) . ? C5 C6 1.367(4) . ? C5 C9 1.386(4) . ? C6 C7 1.388(4) . ? C6 H6 0.9300 . ? C7 C8 1.379(4) . ? C7 H7 0.9300 . ? C8 N7 1.335(4) . ? C8 H8 0.9300 . ? C9 N7 1.336(3) . ? C9 H9 0.9300 . ? C10 N6 1.325(3) . ? C10 N4 1.353(4) . ? C10 C11 1.468(4) . ? C11 N8 1.342(4) . ? C11 C12 1.383(4) . ? C12 C13 1.367(4) . ? C12 H12 0.9300 . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 C15 1.376(5) . ? C14 H14 0.9300 . ? C15 N8 1.336(4) . ? C15 H15 0.9300 . ? C16 O2 1.247(4) . ? C16 O1 1.258(4) . ? C16 C19 1.510(4) . ? C17 O4 1.242(3) . ? C17 O3 1.271(3) . ? C17 C18 1.501(4) . ? C18 C23 1.392(4) . ? C18 C19 1.403(4) . ? C19 C20 1.382(4) . ? C20 C21 1.382(4) . ? C20 H20 0.9300 . ? C21 C22 1.374(5) . ? C21 H21 0.9300 . ? C22 C23 1.377(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N2 N3 1.357(4) . ? N4 N5 1.366(3) . ? N7 Zn1 2.215(2) 2_556 ? O3 Zn1 1.999(2) 2_665 ? O1W H1A 0.8592 . ? O1W H1B 0.8581 . ? 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 O1 Zn1 O3 117.89(9) . 2_665 ? O1 Zn1 N1 138.73(10) . . ? O3 Zn1 N1 103.31(9) 2_665 . ? O1 Zn1 O1W 86.21(8) . . ? O3 Zn1 O1W 94.68(8) 2_665 . ? N1 Zn1 O1W 88.30(9) . . ? O1 Zn1 N7 89.42(9) . 2_556 ? O3 Zn1 N7 90.17(9) 2_665 2_556 ? N1 Zn1 N7 92.92(9) . 2_556 ? O1W Zn1 N7 174.60(9) . 2_556 ? N2 C1 N1 114.0(3) . . ? N2 C1 H1 123.0 . . ? N1 C1 H1 123.0 . . ? N1 C2 N3 110.3(3) . . ? N1 C2 H2 124.9 . . ? N3 C2 H2 124.9 . . ? N3 C3 N4 111.3(2) . . ? N3 C3 H3A 109.4 . . ? N4 C3 H3A 109.4 . . ? N3 C3 H3B 109.4 . . ? N4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N5 C4 N6 115.3(2) . . ? N5 C4 C5 123.7(3) . . ? N6 C4 C5 121.0(2) . . ? C6 C5 C9 118.1(3) . . ? C6 C5 C4 124.6(3) . . ? C9 C5 C4 117.2(3) . . ? C5 C6 C7 118.9(3) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 119.0(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? N7 C8 C7 123.1(3) . . ? N7 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? N7 C9 C5 124.1(3) . . ? N7 C9 H9 117.9 . . ? C5 C9 H9 117.9 . . ? N6 C10 N4 109.6(3) . . ? N6 C10 C11 122.8(3) . . ? N4 C10 C11 127.6(2) . . ? N8 C11 C12 123.4(3) . . ? N8 C11 C10 117.1(3) . . ? C12 C11 C10 119.5(3) . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 118.6(3) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C13 C14 C15 118.9(3) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? N8 C15 C14 124.0(3) . . ? N8 C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? O2 C16 O1 123.2(3) . . ? O2 C16 C19 119.5(3) . . ? O1 C16 C19 117.3(3) . . ? O4 C17 O3 126.6(3) . . ? O4 C17 C18 116.6(2) . . ? O3 C17 C18 116.7(2) . . ? C23 C18 C19 118.6(3) . . ? C23 C18 C17 118.1(3) . . ? C19 C18 C17 123.0(2) . . ? C20 C19 C18 119.3(3) . . ? C20 C19 C16 120.0(3) . . ? C18 C19 C16 120.7(3) . . ? C19 C20 C21 121.0(3) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.6(3) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C18 121.4(3) . . ? C22 C23 H23 119.3 . . ? C18 C23 H23 119.3 . . ? C2 N1 C1 103.2(2) . . ? C2 N1 Zn1 126.1(2) . . ? C1 N1 Zn1 130.0(2) . . ? C1 N2 N3 102.4(2) . . ? C2 N3 N2 110.2(2) . . ? C2 N3 C3 127.2(3) . . ? N2 N3 C3 122.6(2) . . ? C10 N4 N5 109.8(2) . . ? C10 N4 C3 131.8(2) . . ? N5 N4 C3 118.3(2) . . ? C4 N5 N4 102.1(2) . . ? C10 N6 C4 103.3(2) . . ? C8 N7 C9 116.8(3) . . ? C8 N7 Zn1 123.92(18) . 2_556 ? C9 N7 Zn1 119.3(2) . 2_556 ? C15 N8 C11 116.1(3) . . ? C16 O1 Zn1 109.69(18) . . ? C17 O3 Zn1 125.42(19) . 2_665 ? Zn1 O1W H1A 117.0 . . ? Zn1 O1W H1B 94.5 . . ? H1A O1W H1B 113.2 . . ? 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 N5 C4 C5 C6 0.5(5) . . . . ? N6 C4 C5 C6 178.0(3) . . . . ? N5 C4 C5 C9 -176.7(3) . . . . ? N6 C4 C5 C9 0.8(5) . . . . ? C9 C5 C6 C7 0.1(5) . . . . ? C4 C5 C6 C7 -177.1(3) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C6 C7 C8 N7 0.2(6) . . . . ? C6 C5 C9 N7 -0.7(5) . . . . ? C4 C5 C9 N7 176.7(3) . . . . ? N6 C10 C11 N8 161.4(3) . . . . ? N4 C10 C11 N8 -20.2(5) . . . . ? N6 C10 C11 C12 -17.6(5) . . . . ? N4 C10 C11 C12 160.8(3) . . . . ? N8 C11 C12 C13 -0.6(5) . . . . ? C10 C11 C12 C13 178.3(3) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? C13 C14 C15 N8 -0.2(6) . . . . ? O4 C17 C18 C23 -95.9(3) . . . . ? O3 C17 C18 C23 80.0(3) . . . . ? O4 C17 C18 C19 78.7(3) . . . . ? O3 C17 C18 C19 -105.5(3) . . . . ? C23 C18 C19 C20 2.7(4) . . . . ? C17 C18 C19 C20 -171.9(3) . . . . ? C23 C18 C19 C16 -176.1(2) . . . . ? C17 C18 C19 C16 9.3(4) . . . . ? O2 C16 C19 C20 6.5(4) . . . . ? O1 C16 C19 C20 -171.9(3) . . . . ? O2 C16 C19 C18 -174.6(3) . . . . ? O1 C16 C19 C18 6.9(4) . . . . ? C18 C19 C20 C21 -2.0(4) . . . . ? C16 C19 C20 C21 176.8(3) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C20 C21 C22 C23 1.5(5) . . . . ? C21 C22 C23 C18 -0.8(4) . . . . ? C19 C18 C23 C22 -1.3(4) . . . . ? C17 C18 C23 C22 173.5(3) . . . . ? N3 C2 N1 C1 -0.3(3) . . . . ? N3 C2 N1 Zn1 170.45(18) . . . . ? N2 C1 N1 C2 0.4(4) . . . . ? N2 C1 N1 Zn1 -169.8(2) . . . . ? O1 Zn1 N1 C2 5.9(3) . . . . ? O3 Zn1 N1 C2 -177.4(2) 2_665 . . . ? O1W Zn1 N1 C2 88.2(2) . . . . ? N7 Zn1 N1 C2 -86.5(2) 2_556 . . . ? O1 Zn1 N1 C1 174.1(2) . . . . ? O3 Zn1 N1 C1 -9.2(3) 2_665 . . . ? O1W Zn1 N1 C1 -103.6(3) . . . . ? N7 Zn1 N1 C1 81.6(3) 2_556 . . . ? N1 C1 N2 N3 -0.4(3) . . . . ? N1 C2 N3 N2 0.0(3) . . . . ? N1 C2 N3 C3 -179.2(3) . . . . ? C1 N2 N3 C2 0.2(3) . . . . ? C1 N2 N3 C3 179.5(3) . . . . ? N4 C3 N3 C2 116.5(3) . . . . ? N4 C3 N3 N2 -62.7(3) . . . . ? N6 C10 N4 N5 -0.2(4) . . . . ? C11 C10 N4 N5 -178.8(3) . . . . ? N6 C10 N4 C3 177.8(3) . . . . ? C11 C10 N4 C3 -0.8(5) . . . . ? N3 C3 N4 C10 -62.7(4) . . . . ? N3 C3 N4 N5 115.2(3) . . . . ? N6 C4 N5 N4 0.7(4) . . . . ? C5 C4 N5 N4 178.3(3) . . . . ? C10 N4 N5 C4 -0.3(3) . . . . ? C3 N4 N5 C4 -178.6(3) . . . . ? N4 C10 N6 C4 0.6(3) . . . . ? C11 C10 N6 C4 179.3(3) . . . . ? N5 C4 N6 C10 -0.8(4) . . . . ? C5 C4 N6 C10 -178.5(3) . . . . ? C7 C8 N7 C9 -0.8(5) . . . . ? C7 C8 N7 Zn1 178.3(3) . . . 2_556 ? C5 C9 N7 C8 1.0(5) . . . . ? C5 C9 N7 Zn1 -178.1(2) . . . 2_556 ? C14 C15 N8 C11 0.6(6) . . . . ? C12 C11 N8 C15 -0.2(5) . . . . ? C10 C11 N8 C15 -179.2(3) . . . . ? O2 C16 O1 Zn1 -0.3(4) . . . . ? C19 C16 O1 Zn1 178.12(18) . . . . ? O3 Zn1 O1 C16 177.40(18) 2_665 . . . ? N1 Zn1 O1 C16 -6.2(3) . . . . ? O1W Zn1 O1 C16 -89.32(19) . . . . ? N7 Zn1 O1 C16 87.5(2) 2_556 . . . ? O4 C17 O3 Zn1 -18.8(4) . . . 2_665 ? C18 C17 O3 Zn1 165.80(18) . . . 2_665 ? 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 O1W H1A O2 0.86 1.89 2.697(3) 156.9 2_565 O1W H1B O4 0.86 1.75 2.595(3) 166.2 2_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.308 _refine_diff_density_min -0.425 _refine_diff_density_rms 0.067 #========================================================== data_compound-2 _database_code_depnum_ccdc_archive 'CCDC 892066' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 N8 O4 Zn' _chemical_formula_sum 'C23 H16 N8 O4 Zn' _chemical_formula_weight 533.81 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 'C 2/c' _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.1231(10) _cell_length_b 12.5698(4) _cell_length_c 18.1222(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.511(5) _cell_angle_gamma 90.00 _cell_volume 4750.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3689 _cell_measurement_theta_min 3.2839 _cell_measurement_theta_max 29.0920 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 1.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7663 _exptl_absorpt_correction_T_max 0.7968 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9070 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4340 _reflns_number_gt 3345 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0358P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.00072(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4340 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _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 Zn1 Zn 0.278769(14) 0.18367(2) 0.220891(16) 0.02760(12) Uani 1 1 d . . . C1 C 0.35798(14) 0.3881(2) 0.23541(16) 0.0393(7) Uani 1 1 d . . . H1 H 0.3655 0.3908 0.2890 0.047 Uiso 1 1 calc R . . C2 C 0.32239(12) 0.33711(19) 0.11835(14) 0.0282(6) Uani 1 1 d . . . H2 H 0.3013 0.3005 0.0723 0.034 Uiso 1 1 calc R . . C3 C 0.37192(12) 0.4782(2) 0.06095(15) 0.0337(6) Uani 1 1 d . . . H3A H 0.3516 0.5477 0.0536 0.040 Uiso 1 1 calc R . . H3B H 0.3540 0.4385 0.0126 0.040 Uiso 1 1 calc R . . C4 C 0.48786(12) 0.42195(19) 0.08143(14) 0.0278(6) Uani 1 1 d . . . C5 C 0.47961(13) 0.3070(2) 0.06816(15) 0.0323(6) Uani 1 1 d . . . C6 C 0.53208(16) 0.2416(2) 0.08397(18) 0.0510(8) Uani 1 1 d . . . H6 H 0.5734 0.2696 0.1003 0.061 Uiso 1 1 calc R . . C7 C 0.5222(2) 0.1336(3) 0.0751(2) 0.0715(11) Uani 1 1 d . . . H7 H 0.5568 0.0872 0.0855 0.086 Uiso 1 1 calc R . . C8 C 0.4608(2) 0.0954(3) 0.0508(2) 0.0702(11) Uani 1 1 d . . . H8 H 0.4529 0.0226 0.0457 0.084 Uiso 1 1 calc R . . C9 C 0.41174(18) 0.1656(2) 0.0345(2) 0.0573(9) Uani 1 1 d . . . H9 H 0.3701 0.1389 0.0168 0.069 Uiso 1 1 calc R . . C10 C 0.52738(12) 0.57520(19) 0.11191(14) 0.0277(6) Uani 1 1 d . . . C11 C 0.57376(13) 0.66215(19) 0.13706(14) 0.0285(6) Uani 1 1 d . . . C12 C 0.55420(14) 0.7662(2) 0.14150(16) 0.0404(7) Uani 1 1 d . . . H12 H 0.5109 0.7823 0.1284 0.048 Uiso 1 1 calc R . . C13 C 0.59919(15) 0.8446(2) 0.16529(18) 0.0450(8) Uani 1 1 d . . . H13 H 0.5867 0.9146 0.1683 0.054 Uiso 1 1 calc R . . C14 C 0.66341(14) 0.8195(2) 0.18484(15) 0.0354(7) Uani 1 1 d . . . H14 H 0.6937 0.8737 0.2002 0.043 Uiso 1 1 calc R . . C15 C 0.63874(13) 0.64377(19) 0.15863(14) 0.0284(6) Uani 1 1 d . . . H15 H 0.6525 0.5743 0.1566 0.034 Uiso 1 1 calc R . . C16 C 0.29202(13) 0.1345(2) 0.36525(15) 0.0331(6) Uani 1 1 d . . . C17 C 0.28534(13) -0.0535(2) 0.60447(15) 0.0310(6) Uani 1 1 d . . . C18 C 0.30345(13) 0.04298(19) 0.56760(14) 0.0296(6) Uani 1 1 d . . . C19 C 0.33434(16) 0.1287(2) 0.61297(16) 0.0481(8) Uani 1 1 d . . . H19 H 0.3436 0.1271 0.6669 0.058 Uiso 1 1 calc R . . C20 C 0.35124(19) 0.2157(2) 0.57849(18) 0.0626(10) Uani 1 1 d . . . H20 H 0.3721 0.2726 0.6094 0.075 Uiso 1 1 calc R . . C21 C 0.33763(16) 0.2198(2) 0.49886(16) 0.0489(8) Uani 1 1 d . . . H21 H 0.3488 0.2796 0.4760 0.059 Uiso 1 1 calc R . . C22 C 0.30714(13) 0.1346(2) 0.45242(14) 0.0301(6) Uani 1 1 d . . . C23 C 0.29075(12) 0.04713(19) 0.48771(14) 0.0278(6) Uani 1 1 d . . . H23 H 0.2707 -0.0104 0.4569 0.033 Uiso 1 1 calc R . . N1 N 0.32098(10) 0.31143(15) 0.18827(11) 0.0288(5) Uani 1 1 d . . . N2 N 0.38198(11) 0.45727(18) 0.19936(13) 0.0415(6) Uani 1 1 d . . . N3 N 0.35831(10) 0.42290(15) 0.12357(11) 0.0284(5) Uani 1 1 d . . . N4 N 0.44050(10) 0.49110(16) 0.07803(12) 0.0289(5) Uani 1 1 d . . . N5 N 0.46554(10) 0.59006(16) 0.09818(12) 0.0322(5) Uani 1 1 d . . . N6 N 0.54367(10) 0.47282(15) 0.10211(12) 0.0289(5) Uani 1 1 d . . . N7 N 0.41938(12) 0.27074(18) 0.04222(14) 0.0432(6) Uani 1 1 d . . . N8 N 0.68327(10) 0.72015(15) 0.18230(11) 0.0271(5) Uani 1 1 d . . . O1 O 0.31158(10) 0.21275(15) 0.33504(10) 0.0444(5) Uani 1 1 d . . . O2 O 0.26129(11) 0.06088(16) 0.32554(11) 0.0562(6) Uani 1 1 d . . . O3 O 0.25422(9) -0.12554(14) 0.56279(10) 0.0407(5) Uani 1 1 d . . . O4 O 0.30325(10) -0.05461(14) 0.67916(10) 0.0429(5) 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 0.02826(19) 0.02886(18) 0.02545(17) -0.00302(13) 0.00864(13) -0.00402(14) C1 0.0465(19) 0.0414(16) 0.0307(14) -0.0075(13) 0.0137(14) -0.0116(14) C2 0.0229(15) 0.0332(14) 0.0265(14) -0.0022(11) 0.0055(11) -0.0042(12) C3 0.0249(16) 0.0345(15) 0.0402(15) 0.0107(12) 0.0090(13) 0.0000(12) C4 0.0273(16) 0.0293(14) 0.0268(13) 0.0046(11) 0.0090(12) -0.0031(12) C5 0.0344(17) 0.0318(14) 0.0325(14) 0.0004(12) 0.0135(13) -0.0033(13) C6 0.043(2) 0.0366(16) 0.069(2) -0.0043(15) 0.0118(17) 0.0005(15) C7 0.076(3) 0.0356(18) 0.099(3) -0.0045(19) 0.025(2) 0.007(2) C8 0.091(3) 0.0321(18) 0.098(3) -0.0156(18) 0.046(3) -0.014(2) C9 0.060(2) 0.0444(19) 0.077(2) -0.0201(17) 0.035(2) -0.0240(18) C10 0.0250(15) 0.0290(14) 0.0283(13) 0.0062(11) 0.0080(12) -0.0022(12) C11 0.0284(16) 0.0309(14) 0.0268(13) 0.0036(11) 0.0102(12) -0.0019(12) C12 0.0306(17) 0.0331(15) 0.0564(18) 0.0029(14) 0.0132(15) 0.0042(13) C13 0.045(2) 0.0245(14) 0.064(2) -0.0049(13) 0.0162(17) 0.0024(14) C14 0.0393(18) 0.0272(14) 0.0389(15) -0.0046(12) 0.0119(14) -0.0098(13) C15 0.0309(16) 0.0249(12) 0.0305(14) 0.0009(11) 0.0116(12) -0.0012(12) C16 0.0276(16) 0.0390(15) 0.0324(14) 0.0058(13) 0.0099(13) 0.0003(13) C17 0.0327(17) 0.0319(14) 0.0313(15) 0.0054(12) 0.0145(13) 0.0046(13) C18 0.0326(16) 0.0287(13) 0.0282(13) 0.0025(11) 0.0111(12) 0.0000(12) C19 0.074(2) 0.0448(17) 0.0255(14) -0.0023(13) 0.0168(16) -0.0169(16) C20 0.101(3) 0.0489(19) 0.0370(17) -0.0107(15) 0.0211(19) -0.037(2) C21 0.076(3) 0.0364(16) 0.0375(16) 0.0023(13) 0.0235(17) -0.0207(16) C22 0.0308(16) 0.0328(14) 0.0277(13) 0.0011(12) 0.0113(12) -0.0019(12) C23 0.0255(15) 0.0284(13) 0.0287(13) 0.0008(11) 0.0081(12) -0.0008(12) N1 0.0294(13) 0.0302(11) 0.0266(11) -0.0043(9) 0.0089(10) -0.0083(10) N2 0.0448(16) 0.0392(13) 0.0395(13) -0.0091(11) 0.0128(12) -0.0139(12) N3 0.0237(12) 0.0289(11) 0.0328(12) 0.0008(10) 0.0097(10) -0.0058(10) N4 0.0218(13) 0.0282(11) 0.0362(12) 0.0052(10) 0.0090(10) -0.0028(10) N5 0.0272(13) 0.0255(11) 0.0439(13) 0.0054(10) 0.0119(11) -0.0019(10) N6 0.0249(13) 0.0291(11) 0.0325(12) 0.0023(9) 0.0092(10) -0.0017(10) N7 0.0404(16) 0.0408(14) 0.0541(15) -0.0108(12) 0.0232(13) -0.0129(12) N8 0.0262(13) 0.0264(11) 0.0291(11) -0.0021(9) 0.0096(10) -0.0054(10) O1 0.0469(13) 0.0573(13) 0.0295(10) 0.0060(9) 0.0133(10) -0.0153(11) O2 0.0799(18) 0.0525(13) 0.0311(10) -0.0051(10) 0.0117(11) -0.0156(12) O3 0.0463(13) 0.0333(10) 0.0370(10) 0.0056(9) 0.0067(10) -0.0067(10) O4 0.0635(15) 0.0379(10) 0.0282(10) 0.0050(8) 0.0164(10) -0.0069(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O4 1.9418(17) 6 ? Zn1 O1 1.9842(18) . ? Zn1 N1 2.0418(19) . ? Zn1 N8 2.044(2) 3_445 ? C1 N2 1.303(3) . ? C1 N1 1.364(3) . ? C1 H1 0.9300 . ? C2 N1 1.318(3) . ? C2 N3 1.324(3) . ? C2 H2 0.9300 . ? C3 N3 1.446(3) . ? C3 N4 1.453(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N6 1.328(3) . ? C4 N4 1.347(3) . ? C4 C5 1.466(3) . ? C5 N7 1.336(3) . ? C5 C6 1.372(4) . ? C6 C7 1.376(4) . ? C6 H6 0.9300 . ? C7 C8 1.367(5) . ? C7 H7 0.9300 . ? C8 C9 1.353(5) . ? C8 H8 0.9300 . ? C9 N7 1.334(4) . ? C9 H9 0.9300 . ? C10 N5 1.319(3) . ? C10 N6 1.364(3) . ? C10 C11 1.464(3) . ? C11 C15 1.378(3) . ? C11 C12 1.388(3) . ? C12 C13 1.364(4) . ? C12 H12 0.9300 . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 N8 1.330(3) . ? C14 H14 0.9300 . ? C15 N8 1.339(3) . ? C15 H15 0.9300 . ? C16 O2 1.228(3) . ? C16 O1 1.270(3) . ? C16 C22 1.502(3) . ? C17 O3 1.232(3) . ? C17 O4 1.277(3) . ? C17 C18 1.502(3) . ? C18 C23 1.381(3) . ? C18 C19 1.389(4) . ? C19 C20 1.372(4) . ? C19 H19 0.9300 . ? C20 C21 1.373(4) . ? C20 H20 0.9300 . ? C21 C22 1.389(4) . ? C21 H21 0.9300 . ? C22 C23 1.380(3) . ? C23 H23 0.9300 . ? N2 N3 1.366(3) . ? N4 N5 1.361(3) . ? N8 Zn1 2.044(2) 3 ? O4 Zn1 1.9418(17) 6_556 ? 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 O4 Zn1 O1 120.49(8) 6 . ? O4 Zn1 N1 109.29(8) 6 . ? O1 Zn1 N1 96.52(8) . . ? O4 Zn1 N8 116.43(8) 6 3_445 ? O1 Zn1 N8 106.97(8) . 3_445 ? N1 Zn1 N8 104.18(8) . 3_445 ? N2 C1 N1 114.7(2) . . ? N2 C1 H1 122.7 . . ? N1 C1 H1 122.7 . . ? N1 C2 N3 109.7(2) . . ? N1 C2 H2 125.1 . . ? N3 C2 H2 125.1 . . ? N3 C3 N4 111.3(2) . . ? N3 C3 H3A 109.4 . . ? N4 C3 H3A 109.4 . . ? N3 C3 H3B 109.4 . . ? N4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N6 C4 N4 109.7(2) . . ? N6 C4 C5 125.0(2) . . ? N4 C4 C5 125.2(2) . . ? N7 C5 C6 122.9(3) . . ? N7 C5 C4 116.7(2) . . ? C6 C5 C4 120.4(3) . . ? C5 C6 C7 118.4(3) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 118.7(3) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? N7 C9 C8 124.0(3) . . ? N7 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? N5 C10 N6 114.3(2) . . ? N5 C10 C11 121.9(2) . . ? N6 C10 C11 123.8(2) . . ? C15 C11 C12 117.2(2) . . ? C15 C11 C10 121.3(2) . . ? C12 C11 C10 121.4(2) . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? N8 C14 C13 121.9(2) . . ? N8 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? N8 C15 C11 123.8(2) . . ? N8 C15 H15 118.1 . . ? C11 C15 H15 118.1 . . ? O2 C16 O1 122.2(2) . . ? O2 C16 C22 120.2(2) . . ? O1 C16 C22 117.7(2) . . ? O3 C17 O4 123.6(2) . . ? O3 C17 C18 119.9(2) . . ? O4 C17 C18 116.5(2) . . ? C23 C18 C19 118.6(2) . . ? C23 C18 C17 120.4(2) . . ? C19 C18 C17 121.0(2) . . ? C20 C19 C18 120.3(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C20 C21 C22 120.0(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 118.9(2) . . ? C23 C22 C16 119.1(2) . . ? C21 C22 C16 122.1(2) . . ? C22 C23 C18 121.5(2) . . ? C22 C23 H23 119.2 . . ? C18 C23 H23 119.2 . . ? C2 N1 C1 103.1(2) . . ? C2 N1 Zn1 129.12(16) . . ? C1 N1 Zn1 127.67(17) . . ? C1 N2 N3 102.1(2) . . ? C2 N3 N2 110.41(19) . . ? C2 N3 C3 127.8(2) . . ? N2 N3 C3 121.8(2) . . ? C4 N4 N5 109.7(2) . . ? C4 N4 C3 132.8(2) . . ? N5 N4 C3 117.5(2) . . ? C10 N5 N4 102.99(19) . . ? C4 N6 C10 103.3(2) . . ? C9 N7 C5 116.8(3) . . ? C14 N8 C15 117.9(2) . . ? C14 N8 Zn1 120.96(18) . 3 ? C15 N8 Zn1 120.96(17) . 3 ? C16 O1 Zn1 104.36(17) . . ? C17 O4 Zn1 113.21(17) . 6_556 ? 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 N6 C4 C5 N7 -175.4(2) . . . . ? N4 C4 C5 N7 7.9(4) . . . . ? N6 C4 C5 C6 6.2(4) . . . . ? N4 C4 C5 C6 -170.6(2) . . . . ? N7 C5 C6 C7 -2.2(4) . . . . ? C4 C5 C6 C7 176.2(3) . . . . ? C5 C6 C7 C8 0.2(5) . . . . ? C6 C7 C8 C9 1.6(6) . . . . ? C7 C8 C9 N7 -1.6(6) . . . . ? N5 C10 C11 C15 173.5(2) . . . . ? N6 C10 C11 C15 -5.2(4) . . . . ? N5 C10 C11 C12 -5.3(4) . . . . ? N6 C10 C11 C12 176.0(2) . . . . ? C15 C11 C12 C13 1.1(4) . . . . ? C10 C11 C12 C13 180.0(3) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C12 C13 C14 N8 -1.0(4) . . . . ? C12 C11 C15 N8 -0.9(4) . . . . ? C10 C11 C15 N8 -179.8(2) . . . . ? O3 C17 C18 C23 -6.1(4) . . . . ? O4 C17 C18 C23 174.6(2) . . . . ? O3 C17 C18 C19 175.2(3) . . . . ? O4 C17 C18 C19 -4.1(4) . . . . ? C23 C18 C19 C20 0.5(5) . . . . ? C17 C18 C19 C20 179.3(3) . . . . ? C18 C19 C20 C21 0.4(6) . . . . ? C19 C20 C21 C22 -0.8(5) . . . . ? C20 C21 C22 C23 0.3(5) . . . . ? C20 C21 C22 C16 -179.1(3) . . . . ? O2 C16 C22 C23 5.4(4) . . . . ? O1 C16 C22 C23 -175.3(2) . . . . ? O2 C16 C22 C21 -175.2(3) . . . . ? O1 C16 C22 C21 4.2(4) . . . . ? C21 C22 C23 C18 0.6(4) . . . . ? C16 C22 C23 C18 -179.9(2) . . . . ? C19 C18 C23 C22 -1.0(4) . . . . ? C17 C18 C23 C22 -179.7(2) . . . . ? N3 C2 N1 C1 0.5(3) . . . . ? N3 C2 N1 Zn1 -176.16(16) . . . . ? N2 C1 N1 C2 -0.6(3) . . . . ? N2 C1 N1 Zn1 176.12(18) . . . . ? O4 Zn1 N1 C2 49.3(2) 6 . . . ? O1 Zn1 N1 C2 174.8(2) . . . . ? N8 Zn1 N1 C2 -75.8(2) 3_445 . . . ? O4 Zn1 N1 C1 -126.6(2) 6 . . . ? O1 Zn1 N1 C1 -1.0(2) . . . . ? N8 Zn1 N1 C1 108.3(2) 3_445 . . . ? N1 C1 N2 N3 0.4(3) . . . . ? N1 C2 N3 N2 -0.3(3) . . . . ? N1 C2 N3 C3 -179.2(2) . . . . ? C1 N2 N3 C2 -0.1(3) . . . . ? C1 N2 N3 C3 178.9(2) . . . . ? N4 C3 N3 C2 -127.0(3) . . . . ? N4 C3 N3 N2 54.3(3) . . . . ? N6 C4 N4 N5 -1.0(3) . . . . ? C5 C4 N4 N5 176.2(2) . . . . ? N6 C4 N4 C3 -178.0(2) . . . . ? C5 C4 N4 C3 -0.9(4) . . . . ? N3 C3 N4 C4 70.4(3) . . . . ? N3 C3 N4 N5 -106.5(2) . . . . ? N6 C10 N5 N4 -0.2(3) . . . . ? C11 C10 N5 N4 -179.0(2) . . . . ? C4 N4 N5 C10 0.7(2) . . . . ? C3 N4 N5 C10 178.26(19) . . . . ? N4 C4 N6 C10 0.8(2) . . . . ? C5 C4 N6 C10 -176.4(2) . . . . ? N5 C10 N6 C4 -0.4(3) . . . . ? C11 C10 N6 C4 178.4(2) . . . . ? C8 C9 N7 C5 -0.3(5) . . . . ? C6 C5 N7 C9 2.2(4) . . . . ? C4 C5 N7 C9 -176.2(2) . . . . ? C13 C14 N8 C15 1.2(4) . . . . ? C13 C14 N8 Zn1 -174.5(2) . . . 3 ? C11 C15 N8 C14 -0.2(3) . . . . ? C11 C15 N8 Zn1 175.41(17) . . . 3 ? O2 C16 O1 Zn1 1.6(3) . . . . ? C22 C16 O1 Zn1 -177.78(19) . . . . ? O4 Zn1 O1 C16 -59.33(19) 6 . . . ? N1 Zn1 O1 C16 -176.27(17) . . . . ? N8 Zn1 O1 C16 76.71(18) 3_445 . . . ? O3 C17 O4 Zn1 1.8(3) . . . 6_556 ? C18 C17 O4 Zn1 -178.97(17) . . . 6_556 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.345 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.056 #========================================================== data_compound-3 _database_code_depnum_ccdc_archive 'CCDC 892067' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H16 N8 O4 Zn, (H2 O)' _chemical_formula_sum 'C23 H18 N8 O5 Zn' _chemical_formula_weight 551.82 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 triclinic _symmetry_space_group_name_H-M p-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8170(5) _cell_length_b 11.0298(7) _cell_length_c 11.3773(6) _cell_angle_alpha 114.656(6) _cell_angle_beta 104.715(4) _cell_angle_gamma 95.911(5) _cell_volume 1159.00(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2623 _cell_measurement_theta_min 3.3276 _cell_measurement_theta_max 29.1938 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7917 _exptl_absorpt_correction_T_max 0.8247 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7289 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4214 _reflns_number_gt 3418 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0509P)^2^+1.0497P] 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_number_reflns 4214 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Zn1 Zn 0.69586(4) 0.13303(4) 0.15641(4) 0.03175(16) Uani 1 1 d . . . C1 C 0.7220(5) -0.0627(5) -0.1228(4) 0.0488(11) Uani 1 1 d . . . H1 H 0.7221 0.0033 -0.1537 0.059 Uiso 1 1 calc R . . C2 C 0.7185(3) -0.1543(4) 0.0046(3) 0.0313(8) Uani 1 1 d . . . H2 H 0.7154 -0.1718 0.0771 0.038 Uiso 1 1 calc R . . C3 C 0.7233(4) -0.3887(4) -0.1555(4) 0.0360(9) Uani 1 1 d . . . H3A H 0.6460 -0.4446 -0.2350 0.043 Uiso 1 1 calc R . . H3B H 0.7171 -0.4103 -0.0825 0.043 Uiso 1 1 calc R . . C4 C 0.9409(3) -0.5298(3) -0.3188(3) 0.0295(8) Uani 1 1 d . . . C5 C 0.9645(3) -0.6209(3) -0.4447(3) 0.0291(8) Uani 1 1 d . . . C6 C 0.8615(4) -0.6823(4) -0.5663(3) 0.0312(8) Uani 1 1 d . . . H6 H 0.7801 -0.6627 -0.5654 0.037 Uiso 1 1 calc R . . C7 C 0.9896(4) -0.7949(4) -0.6856(4) 0.0421(10) Uani 1 1 d . . . H7 H 0.9985 -0.8555 -0.7677 0.051 Uiso 1 1 calc R . . C8 C 1.0972(4) -0.7373(5) -0.5710(4) 0.0522(11) Uani 1 1 d . . . H8 H 1.1780 -0.7566 -0.5755 0.063 Uiso 1 1 calc R . . C9 C 1.0852(4) -0.6491(4) -0.4468(4) 0.0449(10) Uani 1 1 d . . . H9 H 1.1572 -0.6099 -0.3667 0.054 Uiso 1 1 calc R . . C10 C 0.9666(3) -0.4013(4) -0.1129(3) 0.0297(8) Uani 1 1 d . . . C11 C 1.0234(4) -0.3161(4) 0.0375(3) 0.0334(8) Uani 1 1 d . . . C12 C 1.1549(4) -0.3010(4) 0.1042(4) 0.0419(10) Uani 1 1 d . . . H12 H 1.2090 -0.3432 0.0562 0.050 Uiso 1 1 calc R . . C13 C 1.2025(4) -0.2207(5) 0.2448(4) 0.0509(11) Uani 1 1 d . . . H13 H 1.2901 -0.2080 0.2933 0.061 Uiso 1 1 calc R . . C14 C 1.1199(5) -0.1599(4) 0.3122(4) 0.0499(11) Uani 1 1 d . . . H14 H 1.1510 -0.1049 0.4066 0.060 Uiso 1 1 calc R . . C15 C 0.9914(5) -0.1814(5) 0.2390(4) 0.0532(12) Uani 1 1 d . . . H15 H 0.9359 -0.1404 0.2857 0.064 Uiso 1 1 calc R . . C16 C 0.6141(4) 0.3401(4) 0.1262(4) 0.0362(9) Uani 1 1 d . . . C17 C 0.5572(3) 0.4232(4) 0.0604(4) 0.0308(8) Uani 1 1 d . . . C18 C 0.5009(4) 0.3653(4) -0.0804(4) 0.0342(8) Uani 1 1 d . . . H18 H 0.5014 0.2750 -0.1351 0.041 Uiso 1 1 calc R . . C19 C 0.4437(4) 0.4415(4) -0.1402(4) 0.0377(9) Uani 1 1 d . . . H19 H 0.4055 0.4016 -0.2348 0.045 Uiso 1 1 calc R . . C20 C 0.6292(4) 0.0175(4) 0.3108(3) 0.0336(9) Uani 1 1 d . . . C21 C 0.5601(3) 0.0086(4) 0.4082(3) 0.0285(8) Uani 1 1 d . . . C22 C 0.4823(4) 0.0973(4) 0.4544(3) 0.0330(8) Uani 1 1 d . . . H22 H 0.4705 0.1631 0.4242 0.040 Uiso 1 1 calc R . . C23 C 0.4215(4) 0.0890(4) 0.5455(3) 0.0333(8) Uani 1 1 d . . . H23 H 0.3686 0.1485 0.5756 0.040 Uiso 1 1 calc R . . N1 N 0.7177(3) -0.0350(3) 0.0045(3) 0.0329(7) Uani 1 1 d . . . N2 N 0.7261(4) -0.1871(4) -0.1972(3) 0.0500(9) Uani 1 1 d . . . N3 N 0.7245(3) -0.2450(3) -0.1130(3) 0.0325(7) Uani 1 1 d . . . N4 N 0.8402(3) -0.4232(3) -0.1890(3) 0.0303(7) Uani 1 1 d . . . N5 N 0.8224(3) -0.5066(3) -0.3225(3) 0.0317(7) Uani 1 1 d . . . N6 N 1.0331(3) -0.4663(3) -0.1918(3) 0.0324(7) Uani 1 1 d . . . N7 N 0.8722(3) -0.7688(3) -0.6861(3) 0.0316(7) Uani 1 1 d . . . N8 N 0.9414(3) -0.2589(4) 0.1027(3) 0.0454(8) Uani 1 1 d . . . O1 O 0.6269(3) 0.2238(3) 0.0473(3) 0.0457(7) Uani 1 1 d . . . O2 O 0.6441(3) 0.3855(3) 0.2513(3) 0.0584(8) Uani 1 1 d . . . O3 O 0.5862(3) 0.0876(3) 0.2503(3) 0.0410(7) Uani 1 1 d . . . O4 O 0.7206(3) -0.0387(3) 0.2969(3) 0.0468(7) Uani 1 1 d . . . O1W O 0.5723(5) 0.5743(5) 0.4529(5) 0.1210(17) Uani 1 1 d . . . H1A H 0.6099 0.5194 0.4045 0.181 Uiso 1 1 d R . . H1B H 0.5987 0.6530 0.4597 0.181 Uiso 1 1 d 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 Zn1 0.0420(3) 0.0309(3) 0.0270(2) 0.01387(19) 0.01531(19) 0.01451(19) C1 0.078(3) 0.051(3) 0.039(2) 0.029(2) 0.031(2) 0.038(2) C2 0.038(2) 0.032(2) 0.0267(18) 0.0114(16) 0.0153(16) 0.0164(16) C3 0.034(2) 0.027(2) 0.038(2) 0.0061(17) 0.0125(17) 0.0090(16) C4 0.033(2) 0.0246(19) 0.0273(18) 0.0103(15) 0.0076(16) 0.0077(15) C5 0.0340(19) 0.0246(19) 0.0275(18) 0.0103(15) 0.0116(16) 0.0061(15) C6 0.038(2) 0.0284(19) 0.0302(18) 0.0133(16) 0.0141(16) 0.0155(16) C7 0.047(2) 0.040(2) 0.036(2) 0.0095(18) 0.0205(19) 0.0133(19) C8 0.036(2) 0.066(3) 0.050(3) 0.018(2) 0.019(2) 0.024(2) C9 0.033(2) 0.054(3) 0.037(2) 0.011(2) 0.0105(18) 0.0133(19) C10 0.035(2) 0.0242(18) 0.0271(17) 0.0100(15) 0.0090(16) 0.0085(15) C11 0.046(2) 0.0271(19) 0.0275(18) 0.0123(16) 0.0116(17) 0.0097(17) C12 0.038(2) 0.048(3) 0.034(2) 0.0157(19) 0.0109(18) 0.0059(19) C13 0.041(2) 0.059(3) 0.038(2) 0.020(2) -0.0011(19) -0.005(2) C14 0.067(3) 0.046(3) 0.025(2) 0.0116(19) 0.009(2) 0.004(2) C15 0.071(3) 0.060(3) 0.029(2) 0.014(2) 0.022(2) 0.030(2) C16 0.032(2) 0.036(2) 0.046(2) 0.0249(19) 0.0100(18) 0.0095(17) C17 0.0275(18) 0.031(2) 0.038(2) 0.0196(17) 0.0095(16) 0.0085(15) C18 0.041(2) 0.0242(19) 0.0337(19) 0.0119(16) 0.0089(17) 0.0086(16) C19 0.045(2) 0.034(2) 0.0296(19) 0.0139(17) 0.0076(17) 0.0080(18) C20 0.043(2) 0.029(2) 0.0210(17) 0.0075(16) 0.0097(16) -0.0015(17) C21 0.0316(19) 0.0300(19) 0.0159(15) 0.0054(14) 0.0061(14) 0.0021(15) C22 0.042(2) 0.031(2) 0.0262(18) 0.0143(16) 0.0100(17) 0.0069(17) C23 0.041(2) 0.032(2) 0.0271(18) 0.0106(16) 0.0152(17) 0.0128(17) N1 0.0451(18) 0.0331(18) 0.0238(15) 0.0119(14) 0.0149(14) 0.0191(14) N2 0.080(3) 0.056(2) 0.0314(17) 0.0238(17) 0.0294(18) 0.041(2) N3 0.0366(17) 0.0336(17) 0.0259(15) 0.0090(14) 0.0122(13) 0.0180(14) N4 0.0347(17) 0.0258(16) 0.0248(14) 0.0048(13) 0.0107(13) 0.0128(13) N5 0.0363(17) 0.0275(16) 0.0238(14) 0.0049(13) 0.0085(13) 0.0115(13) N6 0.0349(17) 0.0297(17) 0.0284(16) 0.0097(14) 0.0096(14) 0.0090(14) N7 0.0403(18) 0.0289(17) 0.0267(15) 0.0114(13) 0.0138(14) 0.0111(14) N8 0.055(2) 0.048(2) 0.0285(17) 0.0127(16) 0.0108(16) 0.0232(17) O1 0.0635(19) 0.0364(16) 0.0472(16) 0.0253(14) 0.0195(15) 0.0229(14) O2 0.082(2) 0.060(2) 0.0429(17) 0.0312(16) 0.0164(16) 0.0306(17) O3 0.0448(16) 0.0515(17) 0.0366(14) 0.0258(14) 0.0192(13) 0.0121(13) O4 0.0598(19) 0.0509(18) 0.0449(16) 0.0247(14) 0.0332(15) 0.0221(15) O1W 0.137(4) 0.105(4) 0.115(4) 0.031(3) 0.063(3) 0.035(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O3 1.941(2) . ? Zn1 O1 1.954(3) . ? Zn1 N1 2.026(3) . ? Zn1 N7 2.059(3) 1_566 ? C1 N2 1.290(5) . ? C1 N1 1.364(4) . ? C1 H1 0.9300 . ? C2 N1 1.317(5) . ? C2 N3 1.318(4) . ? C2 H2 0.9300 . ? C3 N3 1.449(5) . ? C3 N4 1.453(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N5 1.326(5) . ? C4 N6 1.361(4) . ? C4 C5 1.471(5) . ? C5 C9 1.376(5) . ? C5 C6 1.377(5) . ? C6 N7 1.341(4) . ? C6 H6 0.9300 . ? C7 N7 1.331(5) . ? C7 C8 1.358(6) . ? C7 H7 0.9300 . ? C8 C9 1.390(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N6 1.318(4) . ? C10 N4 1.354(4) . ? C10 C11 1.481(5) . ? C11 N8 1.340(5) . ? C11 C12 1.387(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C13 C14 1.371(6) . ? C13 H13 0.9300 . ? C14 C15 1.364(6) . ? C14 H14 0.9300 . ? C15 N8 1.342(5) . ? C15 H15 0.9300 . ? C16 O2 1.232(5) . ? C16 O1 1.269(5) . ? C16 C17 1.494(5) . ? C17 C18 1.385(5) . ? C17 C19 1.389(5) 2_665 ? C18 C19 1.386(5) . ? C18 H18 0.9300 . ? C19 C17 1.389(5) 2_665 ? C19 H19 0.9300 . ? C20 O4 1.229(5) . ? C20 O3 1.282(4) . ? C20 C21 1.514(5) . ? C21 C22 1.381(5) . ? C21 C23 1.392(5) 2_656 ? C22 C23 1.389(5) . ? C22 H22 0.9300 . ? C23 C21 1.392(5) 2_656 ? C23 H23 0.9300 . ? N2 N3 1.358(4) . ? N4 N5 1.356(4) . ? N7 Zn1 2.059(3) 1_544 ? O1W H1A 0.8500 . ? O1W H1B 0.8499 . ? 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 O3 Zn1 O1 117.25(12) . . ? O3 Zn1 N1 112.94(12) . . ? O1 Zn1 N1 97.88(12) . . ? O3 Zn1 N7 100.77(11) . 1_566 ? O1 Zn1 N7 118.52(12) . 1_566 ? N1 Zn1 N7 109.91(12) . 1_566 ? N2 C1 N1 115.0(4) . . ? N2 C1 H1 122.5 . . ? N1 C1 H1 122.5 . . ? N1 C2 N3 110.0(3) . . ? N1 C2 H2 125.0 . . ? N3 C2 H2 125.0 . . ? N3 C3 N4 112.4(3) . . ? N3 C3 H3A 109.1 . . ? N4 C3 H3A 109.1 . . ? N3 C3 H3B 109.1 . . ? N4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N5 C4 N6 114.7(3) . . ? N5 C4 C5 120.6(3) . . ? N6 C4 C5 124.7(3) . . ? C9 C5 C6 118.0(3) . . ? C9 C5 C4 123.1(3) . . ? C6 C5 C4 118.9(3) . . ? N7 C6 C5 123.6(3) . . ? N7 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? N7 C7 C8 123.1(4) . . ? N7 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C7 C8 C9 119.3(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C5 C9 C8 118.6(4) . . ? C5 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N6 C10 N4 110.3(3) . . ? N6 C10 C11 124.4(3) . . ? N4 C10 C11 125.3(3) . . ? N8 C11 C12 123.2(3) . . ? N8 C11 C10 116.7(3) . . ? C12 C11 C10 120.0(3) . . ? C13 C12 C11 117.5(4) . . ? C13 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? C14 C13 C12 119.7(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 119.0(4) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? N8 C15 C14 123.1(4) . . ? N8 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? O2 C16 O1 123.6(4) . . ? O2 C16 C17 119.6(4) . . ? O1 C16 C17 116.8(3) . . ? C18 C17 C19 119.0(3) . 2_665 ? C18 C17 C16 120.6(3) . . ? C19 C17 C16 120.4(3) 2_665 . ? C17 C18 C19 120.2(3) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C17 120.8(3) . 2_665 ? C18 C19 H19 119.6 . . ? C17 C19 H19 119.6 2_665 . ? O4 C20 O3 125.3(3) . . ? O4 C20 C21 119.6(3) . . ? O3 C20 C21 115.1(3) . . ? C22 C21 C23 119.6(3) . 2_656 ? C22 C21 C20 121.3(3) . . ? C23 C21 C20 119.1(3) 2_656 . ? C21 C22 C23 120.5(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C21 119.9(3) . 2_656 ? C22 C23 H23 120.0 . . ? C21 C23 H23 120.0 2_656 . ? C2 N1 C1 102.4(3) . . ? C2 N1 Zn1 124.9(2) . . ? C1 N1 Zn1 132.4(3) . . ? C1 N2 N3 102.3(3) . . ? C2 N3 N2 110.3(3) . . ? C2 N3 C3 127.4(3) . . ? N2 N3 C3 122.3(3) . . ? C10 N4 N5 109.4(3) . . ? C10 N4 C3 133.7(3) . . ? N5 N4 C3 116.5(3) . . ? C4 N5 N4 102.6(3) . . ? C10 N6 C4 103.0(3) . . ? C7 N7 C6 117.4(3) . . ? C7 N7 Zn1 127.5(3) . 1_544 ? C6 N7 Zn1 114.5(2) . 1_544 ? C11 N8 C15 117.4(4) . . ? C16 O1 Zn1 108.9(2) . . ? C20 O3 Zn1 115.5(2) . . ? H1A O1W H1B 107.7 . . ? 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 N5 C4 C5 C9 -179.7(4) . . . . ? N6 C4 C5 C9 -1.5(6) . . . . ? N5 C4 C5 C6 -0.3(5) . . . . ? N6 C4 C5 C6 178.0(3) . . . . ? C9 C5 C6 N7 0.6(5) . . . . ? C4 C5 C6 N7 -178.8(3) . . . . ? N7 C7 C8 C9 1.6(7) . . . . ? C6 C5 C9 C8 0.2(6) . . . . ? C4 C5 C9 C8 179.6(4) . . . . ? C7 C8 C9 C5 -1.2(7) . . . . ? N6 C10 C11 N8 -178.9(3) . . . . ? N4 C10 C11 N8 1.4(5) . . . . ? N6 C10 C11 C12 -0.1(5) . . . . ? N4 C10 C11 C12 -179.8(3) . . . . ? N8 C11 C12 C13 -1.1(6) . . . . ? C10 C11 C12 C13 -179.8(4) . . . . ? C11 C12 C13 C14 0.0(6) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C13 C14 C15 N8 -0.5(7) . . . . ? O2 C16 C17 C18 -168.2(4) . . . . ? O1 C16 C17 C18 10.8(5) . . . . ? O2 C16 C17 C19 9.8(6) . . . 2_665 ? O1 C16 C17 C19 -171.3(3) . . . 2_665 ? C19 C17 C18 C19 -0.5(6) 2_665 . . . ? C16 C17 C18 C19 177.5(3) . . . . ? C17 C18 C19 C17 0.5(6) . . . 2_665 ? O4 C20 C21 C22 162.9(3) . . . . ? O3 C20 C21 C22 -16.1(5) . . . . ? O4 C20 C21 C23 -15.5(5) . . . 2_656 ? O3 C20 C21 C23 165.6(3) . . . 2_656 ? C23 C21 C22 C23 -0.5(6) 2_656 . . . ? C20 C21 C22 C23 -178.9(3) . . . . ? C21 C22 C23 C21 0.5(6) . . . 2_656 ? N3 C2 N1 C1 0.7(4) . . . . ? N3 C2 N1 Zn1 175.2(2) . . . . ? N2 C1 N1 C2 -0.4(5) . . . . ? N2 C1 N1 Zn1 -174.3(3) . . . . ? O3 Zn1 N1 C2 -31.5(3) . . . . ? O1 Zn1 N1 C2 -155.6(3) . . . . ? N7 Zn1 N1 C2 80.1(3) 1_566 . . . ? O3 Zn1 N1 C1 141.3(4) . . . . ? O1 Zn1 N1 C1 17.2(4) . . . . ? N7 Zn1 N1 C1 -107.1(4) 1_566 . . . ? N1 C1 N2 N3 -0.1(5) . . . . ? N1 C2 N3 N2 -0.8(4) . . . . ? N1 C2 N3 C3 -178.0(3) . . . . ? C1 N2 N3 C2 0.5(4) . . . . ? C1 N2 N3 C3 177.8(4) . . . . ? N4 C3 N3 C2 -121.1(4) . . . . ? N4 C3 N3 N2 62.0(4) . . . . ? N6 C10 N4 N5 0.6(4) . . . . ? C11 C10 N4 N5 -179.7(3) . . . . ? N6 C10 N4 C3 173.1(3) . . . . ? C11 C10 N4 C3 -7.1(6) . . . . ? N3 C3 N4 C10 75.9(5) . . . . ? N3 C3 N4 N5 -112.0(3) . . . . ? N6 C4 N5 N4 -0.3(4) . . . . ? C5 C4 N5 N4 178.2(3) . . . . ? C10 N4 N5 C4 -0.2(4) . . . . ? C3 N4 N5 C4 -174.2(3) . . . . ? N4 C10 N6 C4 -0.7(4) . . . . ? C11 C10 N6 C4 179.6(3) . . . . ? N5 C4 N6 C10 0.6(4) . . . . ? C5 C4 N6 C10 -177.8(3) . . . . ? C8 C7 N7 C6 -0.7(6) . . . . ? C8 C7 N7 Zn1 -170.8(3) . . . 1_544 ? C5 C6 N7 C7 -0.4(5) . . . . ? C5 C6 N7 Zn1 170.9(3) . . . 1_544 ? C12 C11 N8 C15 1.3(6) . . . . ? C10 C11 N8 C15 -180.0(4) . . . . ? C14 C15 N8 C11 -0.5(6) . . . . ? O2 C16 O1 Zn1 1.3(5) . . . . ? C17 C16 O1 Zn1 -177.6(2) . . . . ? O3 Zn1 O1 C16 63.7(3) . . . . ? N1 Zn1 O1 C16 -175.4(3) . . . . ? N7 Zn1 O1 C16 -57.6(3) 1_566 . . . ? O4 C20 O3 Zn1 -11.4(5) . . . . ? C21 C20 O3 Zn1 167.4(2) . . . . ? O1 Zn1 O3 C20 174.1(2) . . . . ? N1 Zn1 O3 C20 61.4(3) . . . . ? N7 Zn1 O3 C20 -55.7(3) 1_566 . . . ? 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 O1W H1A O2 0.85 1.91 2.730(6) 161.8 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.351 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.074 #========================================================== data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 892068' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H17 N8 O7.50 Zn2' _chemical_formula_sum 'C24 H17 N8 O7.50 Zn2' _chemical_formula_weight 668.20 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 'C 2/c' _symmetry_space_group_name_hall 'C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.9785(7) _cell_length_b 10.1939(2) _cell_length_c 19.4052(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.070(3) _cell_angle_gamma 90.00 _cell_volume 5043.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4162 _cell_measurement_theta_min 3.1399 _cell_measurement_theta_max 29.0982 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2696 _exptl_absorpt_coefficient_mu 1.968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6495 _exptl_absorpt_correction_T_max 0.7062 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9907 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4610 _reflns_number_gt 3780 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0509P)^2^+14.3040P] 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_number_reflns 4610 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Zn1 Zn -0.051680(16) 0.09109(4) 0.11429(2) 0.03182(14) Uani 1 1 d . . . Zn2 Zn -0.09807(2) 0.28527(5) -0.01793(2) 0.04759(17) Uani 1 1 d . . . C1 C 0.06699(17) 0.1068(4) 0.1697(2) 0.0488(11) Uani 1 1 d . . . H1 H 0.0643 0.0693 0.2125 0.059 Uiso 1 1 calc R . . C2 C 0.04603(14) 0.1760(4) 0.0667(2) 0.0355(9) Uani 1 1 d . . . H2 H 0.0275 0.1990 0.0225 0.043 Uiso 1 1 calc R . . C3 C 0.13230(14) 0.2685(4) 0.0546(2) 0.0326(8) Uani 1 1 d . . . H3A H 0.1156 0.2868 0.0064 0.039 Uiso 1 1 calc R . . H3B H 0.1400 0.3517 0.0786 0.039 Uiso 1 1 calc R . . C4 C 0.23051(15) 0.0631(4) 0.0198(2) 0.0358(9) Uani 1 1 d . . . C5 C 0.24999(15) -0.0402(4) -0.0213(2) 0.0370(9) Uani 1 1 d . . . C6 C 0.30247(16) -0.0729(4) -0.0065(2) 0.0395(9) Uani 1 1 d . . . H6 H 0.3244 -0.0292 0.0298 0.047 Uiso 1 1 calc R . . C7 C 0.2914(2) -0.2270(4) -0.0943(2) 0.0533(12) Uani 1 1 d . . . H7 H 0.3055 -0.2907 -0.1196 0.064 Uiso 1 1 calc R . . C8 C 0.2392(2) -0.2003(5) -0.1117(3) 0.0586(13) Uani 1 1 d . . . H8 H 0.2182 -0.2455 -0.1482 0.070 Uiso 1 1 calc R . . C9 C 0.21758(19) -0.1068(4) -0.0753(2) 0.0504(11) Uani 1 1 d . . . H9 H 0.1819 -0.0882 -0.0865 0.060 Uiso 1 1 calc R . . C10 C 0.22952(14) 0.2143(4) 0.0937(2) 0.0338(8) Uani 1 1 d . . . C11 C 0.24615(15) 0.3085(4) 0.1510(2) 0.0369(9) Uani 1 1 d . . . C12 C 0.29824(17) 0.3173(5) 0.1812(2) 0.0533(12) Uani 1 1 d . . . H12 H 0.3229 0.2644 0.1657 0.064 Uiso 1 1 calc R . . C13 C 0.3134(2) 0.4061(5) 0.2350(3) 0.0647(14) Uani 1 1 d . . . H13 H 0.3485 0.4159 0.2556 0.078 Uiso 1 1 calc R . . C14 C 0.2754(2) 0.4798(5) 0.2573(3) 0.0594(12) Uani 1 1 d . . . H14 H 0.2843 0.5394 0.2940 0.071 Uiso 1 1 calc R . . C15 C 0.2248(2) 0.4640(5) 0.2249(3) 0.0596(13) Uani 1 1 d . . . H15 H 0.1995 0.5146 0.2405 0.071 Uiso 1 1 calc R . . C16 C -0.07581(17) 0.4042(4) -0.1369(2) 0.0432(10) Uani 1 1 d . . . C17 C -0.05971(14) 0.1508(3) -0.35314(19) 0.0287(8) Uani 1 1 d . . . C18 C -0.07301(16) 0.6357(4) -0.3672(2) 0.0428(10) Uani 1 1 d . . . C19 C -0.07150(14) 0.5142(3) -0.3230(2) 0.0348(8) Uani 1 1 d . . . C20 C -0.07395(15) 0.5175(3) -0.2518(2) 0.0385(9) Uani 1 1 d . . . H20 H -0.0764 0.5976 -0.2297 0.046 Uiso 1 1 calc R . . C21 C -0.07272(14) 0.4020(3) -0.2138(2) 0.0339(8) Uani 1 1 d . . . C22 C -0.06818(13) 0.2831(3) -0.24626(19) 0.0286(8) Uani 1 1 d . . . H22 H -0.0670 0.2058 -0.2205 0.034 Uiso 1 1 calc R . . C23 C -0.06529(13) 0.2777(3) -0.31722(19) 0.0273(7) Uani 1 1 d . . . C24 C -0.06688(14) 0.3942(3) -0.3547(2) 0.0330(8) Uani 1 1 d . . . H24 H -0.0648 0.3916 -0.4019 0.040 Uiso 1 1 calc R . . N1 N 0.02539(12) 0.1210(3) 0.11642(16) 0.0342(7) Uani 1 1 d . . . N2 N 0.11135(14) 0.1502(4) 0.15590(19) 0.0511(9) Uani 1 1 d . . . N3 N 0.09657(11) 0.1936(3) 0.08864(15) 0.0299(7) Uani 1 1 d . . . N4 N 0.18065(11) 0.1982(3) 0.05512(16) 0.0327(7) Uani 1 1 d . . . N5 N 0.18075(12) 0.0995(3) 0.00776(17) 0.0384(8) Uani 1 1 d . . . N6 N 0.26188(12) 0.1305(3) 0.07185(17) 0.0366(7) Uani 1 1 d . . . N7 N 0.32332(14) -0.1646(3) -0.04209(17) 0.0439(8) Uani 1 1 d . . . N8 N 0.20885(14) 0.3802(4) 0.1719(2) 0.0510(9) Uani 1 1 d . . . O1 O -0.08125(14) 0.2916(3) -0.11025(16) 0.0575(9) Uani 1 1 d . . . O2 O -0.07328(17) 0.5078(3) -0.10486(18) 0.0781(12) Uani 1 1 d . . . O3 O -0.06361(11) 0.0449(2) -0.31921(13) 0.0368(6) Uani 1 1 d . . . O4 O -0.05193(13) 0.1499(3) -0.41382(14) 0.0476(7) Uani 1 1 d . . . O5 O -0.07545(17) 0.6171(3) -0.43234(18) 0.0723(11) Uani 1 1 d . . . O6 O -0.06939(13) 0.7446(3) -0.33728(17) 0.0521(8) Uani 1 1 d . . . O7 O -0.09098(13) 0.1109(3) 0.02012(15) 0.0539(8) Uani 1 1 d . . . O1W O -0.0118(7) 0.5854(15) -0.4996(8) 0.204(8) Uani 0.50 1 d P . . H1A H -0.0444 0.6017 -0.5126 0.305 Uiso 0.50 1 d PR . . H1B H -0.0017 0.6185 -0.4594 0.305 Uiso 0.50 1 d PR . . 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 0.0325(2) 0.0261(2) 0.0394(3) 0.00926(18) 0.01327(19) 0.00122(17) Zn2 0.0676(4) 0.0439(3) 0.0332(3) 0.0042(2) 0.0146(2) 0.0227(2) C1 0.046(3) 0.057(3) 0.045(2) 0.023(2) 0.012(2) 0.004(2) C2 0.0267(19) 0.049(2) 0.0312(19) 0.0029(18) 0.0073(16) -0.0014(17) C3 0.0261(18) 0.0320(19) 0.041(2) 0.0021(16) 0.0085(16) 0.0002(15) C4 0.033(2) 0.035(2) 0.042(2) 0.0013(17) 0.0142(17) 0.0007(17) C5 0.039(2) 0.034(2) 0.041(2) 0.0022(17) 0.0135(18) -0.0010(17) C6 0.043(2) 0.038(2) 0.040(2) 0.0000(18) 0.0150(19) 0.0050(18) C7 0.067(3) 0.046(3) 0.049(3) -0.007(2) 0.017(2) 0.012(2) C8 0.067(3) 0.054(3) 0.054(3) -0.016(2) 0.010(2) -0.004(2) C9 0.048(3) 0.050(3) 0.055(3) -0.011(2) 0.014(2) -0.004(2) C10 0.030(2) 0.034(2) 0.041(2) 0.0029(17) 0.0145(17) 0.0004(16) C11 0.034(2) 0.037(2) 0.041(2) 0.0007(18) 0.0106(17) -0.0011(17) C12 0.036(2) 0.058(3) 0.063(3) -0.018(2) 0.003(2) 0.009(2) C13 0.044(3) 0.072(3) 0.070(3) -0.023(3) -0.010(2) 0.003(2) C14 0.065(3) 0.056(3) 0.053(3) -0.014(2) 0.003(2) 0.002(3) C15 0.055(3) 0.060(3) 0.067(3) -0.022(3) 0.018(3) 0.005(2) C16 0.044(2) 0.044(2) 0.043(2) -0.010(2) 0.0117(19) 0.0096(19) C17 0.0291(18) 0.0219(17) 0.035(2) -0.0003(15) 0.0052(15) -0.0002(14) C18 0.044(2) 0.0228(19) 0.061(3) 0.0039(19) 0.007(2) -0.0024(17) C19 0.033(2) 0.0206(17) 0.048(2) 0.0012(16) 0.0022(17) -0.0028(15) C20 0.036(2) 0.0216(18) 0.056(3) -0.0091(18) 0.0043(18) 0.0013(16) C21 0.0301(19) 0.0305(19) 0.041(2) -0.0063(17) 0.0079(17) 0.0036(15) C22 0.0278(18) 0.0222(17) 0.0358(19) -0.0009(15) 0.0063(15) 0.0001(14) C23 0.0251(18) 0.0200(16) 0.0361(19) -0.0016(14) 0.0044(15) -0.0008(13) C24 0.035(2) 0.0273(19) 0.035(2) 0.0006(16) 0.0026(17) -0.0032(16) N1 0.0319(17) 0.0350(17) 0.0380(17) 0.0021(14) 0.0125(14) 0.0006(14) N2 0.0375(19) 0.069(2) 0.045(2) 0.0210(19) 0.0029(16) -0.0020(18) N3 0.0249(15) 0.0331(16) 0.0331(16) 0.0015(13) 0.0094(13) 0.0005(13) N4 0.0249(16) 0.0338(16) 0.0410(18) -0.0038(14) 0.0102(14) -0.0012(13) N5 0.0326(18) 0.0393(18) 0.0452(19) -0.0068(15) 0.0126(15) -0.0014(14) N6 0.0309(17) 0.0390(17) 0.0411(18) -0.0040(15) 0.0100(15) -0.0004(14) N7 0.050(2) 0.047(2) 0.0366(18) -0.0001(16) 0.0133(17) 0.0124(17) N8 0.038(2) 0.054(2) 0.062(2) -0.0157(19) 0.0116(18) 0.0007(17) O1 0.082(2) 0.057(2) 0.0411(17) -0.0074(15) 0.0314(17) 0.0023(17) O2 0.115(3) 0.057(2) 0.057(2) -0.0281(18) 0.003(2) 0.027(2) O3 0.0610(18) 0.0190(12) 0.0344(14) 0.0001(11) 0.0191(13) 0.0016(12) O4 0.082(2) 0.0343(15) 0.0322(15) -0.0022(12) 0.0247(15) -0.0029(14) O5 0.121(3) 0.0324(16) 0.054(2) 0.0096(15) -0.005(2) 0.0011(18) O6 0.074(2) 0.0208(13) 0.069(2) 0.0011(14) 0.0325(18) -0.0052(13) O7 0.076(2) 0.0343(15) 0.0456(17) 0.0052(13) -0.0034(16) 0.0139(15) O1W 0.211(17) 0.237(18) 0.138(11) -0.053(12) -0.028(11) 0.078(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O7 1.925(3) . ? Zn1 O3 1.959(2) 6_556 ? Zn1 O6 2.017(3) 6_566 ? Zn1 N1 2.018(3) . ? Zn1 C17 2.564(3) 6_556 ? Zn2 O7 1.920(3) . ? Zn2 O1 1.925(3) . ? Zn2 O5 1.928(3) 6_566 ? Zn2 N7 2.070(3) 3_455 ? C1 N2 1.309(5) . ? C1 N1 1.352(5) . ? C1 H1 0.9300 . ? C2 N3 1.313(5) . ? C2 N1 1.315(5) . ? C2 H2 0.9300 . ? C3 N4 1.445(4) . ? C3 N3 1.455(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N5 1.322(5) . ? C4 N6 1.356(5) . ? C4 C5 1.468(5) . ? C5 C6 1.379(5) . ? C5 C9 1.389(6) . ? C6 N7 1.337(5) . ? C6 H6 0.9300 . ? C7 N7 1.339(6) . ? C7 C8 1.361(7) . ? C7 H7 0.9300 . ? C8 C9 1.369(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N6 1.324(5) . ? C10 N4 1.354(5) . ? C10 C11 1.470(5) . ? C11 N8 1.337(5) . ? C11 C12 1.370(6) . ? C12 C13 1.381(6) . ? C12 H12 0.9300 . ? C13 C14 1.374(7) . ? C13 H13 0.9300 . ? C14 C15 1.353(7) . ? C14 H14 0.9300 . ? C15 N8 1.341(6) . ? C15 H15 0.9300 . ? C16 O2 1.220(5) . ? C16 O1 1.278(5) . ? C16 C21 1.510(5) . ? C17 O4 1.232(4) . ? C17 O3 1.278(4) . ? C17 C23 1.490(5) . ? C17 Zn1 2.564(3) 6 ? C18 O6 1.248(5) . ? C18 O5 1.268(5) . ? C18 C19 1.502(5) . ? C19 C24 1.385(5) . ? C19 C20 1.396(6) . ? C20 C21 1.386(5) . ? C20 H20 0.9300 . ? C21 C22 1.382(5) . ? C22 C23 1.394(5) . ? C22 H22 0.9300 . ? C23 C24 1.388(5) . ? C24 H24 0.9300 . ? N2 N3 1.362(4) . ? N4 N5 1.363(4) . ? N7 Zn2 2.070(3) 3_545 ? O3 Zn1 1.959(2) 6 ? O5 Zn2 1.928(3) 6_565 ? O6 Zn1 2.017(3) 6_565 ? O1W H1A 0.8516 . ? O1W H1B 0.8432 . ? 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 O7 Zn1 O3 125.26(13) . 6_556 ? O7 Zn1 O6 103.21(13) . 6_566 ? O3 Zn1 O6 101.65(11) 6_556 6_566 ? O7 Zn1 N1 110.30(14) . . ? O3 Zn1 N1 112.04(12) 6_556 . ? O6 Zn1 N1 100.33(13) 6_566 . ? O7 Zn1 C17 106.34(12) . 6_556 ? O3 Zn1 C17 29.09(10) 6_556 6_556 ? O6 Zn1 C17 130.34(11) 6_566 6_556 ? N1 Zn1 C17 105.51(12) . 6_556 ? O7 Zn2 O1 111.51(13) . . ? O7 Zn2 O5 98.95(13) . 6_566 ? O1 Zn2 O5 134.29(16) . 6_566 ? O7 Zn2 N7 109.46(14) . 3_455 ? O1 Zn2 N7 99.87(14) . 3_455 ? O5 Zn2 N7 101.07(16) 6_566 3_455 ? N2 C1 N1 114.4(4) . . ? N2 C1 H1 122.8 . . ? N1 C1 H1 122.8 . . ? N3 C2 N1 110.1(3) . . ? N3 C2 H2 124.9 . . ? N1 C2 H2 124.9 . . ? N4 C3 N3 111.4(3) . . ? N4 C3 H3A 109.3 . . ? N3 C3 H3A 109.3 . . ? N4 C3 H3B 109.3 . . ? N3 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N5 C4 N6 114.6(3) . . ? N5 C4 C5 122.2(4) . . ? N6 C4 C5 123.1(3) . . ? C6 C5 C9 118.0(4) . . ? C6 C5 C4 119.4(4) . . ? C9 C5 C4 122.6(4) . . ? N7 C6 C5 123.0(4) . . ? N7 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? N7 C7 C8 122.3(4) . . ? N7 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C7 C8 C9 120.0(5) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C5 118.7(4) . . ? C8 C9 H9 120.7 . . ? C5 C9 H9 120.7 . . ? N6 C10 N4 109.3(3) . . ? N6 C10 C11 123.4(3) . . ? N4 C10 C11 127.3(3) . . ? N8 C11 C12 123.3(4) . . ? N8 C11 C10 117.5(3) . . ? C12 C11 C10 119.2(4) . . ? C11 C12 C13 118.7(4) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 118.7(4) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 118.7(4) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N8 C15 C14 124.2(4) . . ? N8 C15 H15 117.9 . . ? C14 C15 H15 117.9 . . ? O2 C16 O1 124.8(4) . . ? O2 C16 C21 120.5(4) . . ? O1 C16 C21 114.7(3) . . ? O4 C17 O3 122.0(3) . . ? O4 C17 C23 120.1(3) . . ? O3 C17 C23 117.9(3) . . ? O4 C17 Zn1 73.8(2) . 6 ? O3 C17 Zn1 48.18(16) . 6 ? C23 C17 Zn1 166.0(3) . 6 ? O6 C18 O5 125.5(4) . . ? O6 C18 C19 118.5(4) . . ? O5 C18 C19 115.9(3) . . ? C24 C19 C20 119.0(3) . . ? C24 C19 C18 118.0(4) . . ? C20 C19 C18 123.0(3) . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 C16 119.3(3) . . ? C20 C21 C16 120.9(3) . . ? C21 C22 C23 120.7(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 118.8(3) . . ? C24 C23 C17 119.6(3) . . ? C22 C23 C17 121.6(3) . . ? C19 C24 C23 121.3(3) . . ? C19 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C2 N1 C1 103.1(3) . . ? C2 N1 Zn1 126.3(3) . . ? C1 N1 Zn1 130.1(3) . . ? C1 N2 N3 102.0(3) . . ? C2 N3 N2 110.3(3) . . ? C2 N3 C3 127.6(3) . . ? N2 N3 C3 121.3(3) . . ? C10 N4 N5 109.8(3) . . ? C10 N4 C3 131.7(3) . . ? N5 N4 C3 118.4(3) . . ? C4 N5 N4 102.5(3) . . ? C10 N6 C4 103.7(3) . . ? C6 N7 C7 118.0(4) . . ? C6 N7 Zn2 122.4(3) . 3_545 ? C7 N7 Zn2 119.6(3) . 3_545 ? C11 N8 C15 116.4(4) . . ? C16 O1 Zn2 117.9(3) . . ? C17 O3 Zn1 102.7(2) . 6 ? C18 O5 Zn2 136.9(3) . 6_565 ? C18 O6 Zn1 121.7(3) . 6_565 ? Zn2 O7 Zn1 117.15(15) . . ? H1A O1W H1B 108.2 . . ? 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 N5 C4 C5 C6 179.5(4) . . . . ? N6 C4 C5 C6 0.8(6) . . . . ? N5 C4 C5 C9 -0.1(6) . . . . ? N6 C4 C5 C9 -178.8(4) . . . . ? C9 C5 C6 N7 0.5(6) . . . . ? C4 C5 C6 N7 -179.1(4) . . . . ? N7 C7 C8 C9 0.1(7) . . . . ? C7 C8 C9 C5 0.4(7) . . . . ? C6 C5 C9 C8 -0.7(6) . . . . ? C4 C5 C9 C8 178.9(4) . . . . ? N6 C10 C11 N8 -174.6(4) . . . . ? N4 C10 C11 N8 5.6(6) . . . . ? N6 C10 C11 C12 4.3(6) . . . . ? N4 C10 C11 C12 -175.5(4) . . . . ? N8 C11 C12 C13 -1.2(7) . . . . ? C10 C11 C12 C13 180.0(4) . . . . ? C11 C12 C13 C14 1.6(8) . . . . ? C12 C13 C14 C15 -1.1(8) . . . . ? C13 C14 C15 N8 0.1(8) . . . . ? O6 C18 C19 C24 -169.6(4) . . . . ? O5 C18 C19 C24 7.2(6) . . . . ? O6 C18 C19 C20 9.6(6) . . . . ? O5 C18 C19 C20 -173.6(4) . . . . ? C24 C19 C20 C21 -1.2(6) . . . . ? C18 C19 C20 C21 179.6(4) . . . . ? C19 C20 C21 C22 1.1(6) . . . . ? C19 C20 C21 C16 -179.5(3) . . . . ? O2 C16 C21 C22 170.9(4) . . . . ? O1 C16 C21 C22 -9.3(5) . . . . ? O2 C16 C21 C20 -8.6(6) . . . . ? O1 C16 C21 C20 171.2(4) . . . . ? C20 C21 C22 C23 -0.6(5) . . . . ? C16 C21 C22 C23 179.9(3) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C21 C22 C23 C17 179.2(3) . . . . ? O4 C17 C23 C24 6.4(5) . . . . ? O3 C17 C23 C24 -173.2(3) . . . . ? Zn1 C17 C23 C24 -178.1(9) 6 . . . ? O4 C17 C23 C22 -172.6(3) . . . . ? O3 C17 C23 C22 7.8(5) . . . . ? Zn1 C17 C23 C22 2.8(12) 6 . . . ? C20 C19 C24 C23 0.8(6) . . . . ? C18 C19 C24 C23 -179.9(3) . . . . ? C22 C23 C24 C19 -0.3(5) . . . . ? C17 C23 C24 C19 -179.4(3) . . . . ? N3 C2 N1 C1 0.0(4) . . . . ? N3 C2 N1 Zn1 172.7(2) . . . . ? N2 C1 N1 C2 0.4(5) . . . . ? N2 C1 N1 Zn1 -171.8(3) . . . . ? O7 Zn1 N1 C2 15.3(4) . . . . ? O3 Zn1 N1 C2 159.7(3) 6_556 . . . ? O6 Zn1 N1 C2 -93.1(3) 6_566 . . . ? C17 Zn1 N1 C2 129.7(3) 6_556 . . . ? O7 Zn1 N1 C1 -174.1(3) . . . . ? O3 Zn1 N1 C1 -29.6(4) 6_556 . . . ? O6 Zn1 N1 C1 77.5(4) 6_566 . . . ? C17 Zn1 N1 C1 -59.7(4) 6_556 . . . ? N1 C1 N2 N3 -0.7(5) . . . . ? N1 C2 N3 N2 -0.4(5) . . . . ? N1 C2 N3 C3 -169.8(3) . . . . ? C1 N2 N3 C2 0.7(4) . . . . ? C1 N2 N3 C3 170.8(3) . . . . ? N4 C3 N3 C2 -135.5(4) . . . . ? N4 C3 N3 N2 56.2(4) . . . . ? N6 C10 N4 N5 1.2(4) . . . . ? C11 C10 N4 N5 -178.9(3) . . . . ? N6 C10 N4 C3 -175.8(3) . . . . ? C11 C10 N4 C3 4.0(6) . . . . ? N3 C3 N4 C10 -105.2(4) . . . . ? N3 C3 N4 N5 78.0(4) . . . . ? N6 C4 N5 N4 0.7(4) . . . . ? C5 C4 N5 N4 -178.1(3) . . . . ? C10 N4 N5 C4 -1.2(4) . . . . ? C3 N4 N5 C4 176.4(3) . . . . ? N4 C10 N6 C4 -0.7(4) . . . . ? C11 C10 N6 C4 179.4(3) . . . . ? N5 C4 N6 C10 0.0(4) . . . . ? C5 C4 N6 C10 178.8(3) . . . . ? C5 C6 N7 C7 0.0(6) . . . . ? C5 C6 N7 Zn2 -178.8(3) . . . 3_545 ? C8 C7 N7 C6 -0.3(7) . . . . ? C8 C7 N7 Zn2 178.6(4) . . . 3_545 ? C12 C11 N8 C15 0.2(7) . . . . ? C10 C11 N8 C15 179.1(4) . . . . ? C14 C15 N8 C11 0.3(7) . . . . ? O2 C16 O1 Zn2 10.7(6) . . . . ? C21 C16 O1 Zn2 -169.1(3) . . . . ? O7 Zn2 O1 C16 -168.5(3) . . . . ? O5 Zn2 O1 C16 -40.4(4) 6_566 . . . ? N7 Zn2 O1 C16 75.9(3) 3_455 . . . ? O4 C17 O3 Zn1 2.1(4) . . . 6 ? C23 C17 O3 Zn1 -178.4(3) . . . 6 ? O6 C18 O5 Zn2 -25.9(8) . . . 6_565 ? C19 C18 O5 Zn2 157.6(4) . . . 6_565 ? O5 C18 O6 Zn1 -13.0(6) . . . 6_565 ? C19 C18 O6 Zn1 163.4(3) . . . 6_565 ? O1 Zn2 O7 Zn1 131.25(19) . . . . ? O5 Zn2 O7 Zn1 -14.0(2) 6_566 . . . ? N7 Zn2 O7 Zn1 -119.19(18) 3_455 . . . ? O3 Zn1 O7 Zn2 150.06(14) 6_556 . . . ? O6 Zn1 O7 Zn2 35.2(2) 6_566 . . . ? N1 Zn1 O7 Zn2 -71.2(2) . . . . ? C17 Zn1 O7 Zn2 174.84(16) 6_556 . . . ? 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 O1W H1A O1 0.85 2.23 2.820(15) 125.9 6_565 O1W H1B O2 0.84 2.39 2.811(15) 111.9 2_554 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.674 _refine_diff_density_min -1.308 _refine_diff_density_rms 0.078 #========================================================== data_compound-5 _database_code_depnum_ccdc_archive 'CCDC 892069' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 N8 O6 Zn' _chemical_formula_sum 'C20 H17 N8 O6 Zn' _chemical_formula_weight 530.79 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 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8534(5) _cell_length_b 15.0975(5) _cell_length_c 12.5650(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.268(5) _cell_angle_gamma 90.00 _cell_volume 2095.45(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2939 _cell_measurement_theta_min 3.2456 _cell_measurement_theta_max 29.1665 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7733 _exptl_absorpt_correction_T_max 0.8179 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7768 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3822 _reflns_number_gt 3084 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0600P)^2^+1.0798P] 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_number_reflns 3822 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Zn1 Zn 0.86530(3) 0.16955(2) -0.17793(3) 0.02496(15) Uani 1 1 d . . . C1 C 0.8828(3) 0.0891(2) 0.0541(3) 0.0352(8) Uani 1 1 d . . . H1 H 0.9048 0.1427 0.0926 0.042 Uiso 1 1 calc R . . C2 C 0.8421(3) -0.0065(2) -0.0774(3) 0.0279(7) Uani 1 1 d . . . H2 H 0.8294 -0.0360 -0.1458 0.033 Uiso 1 1 calc R . . C3 C 0.7905(3) -0.1310(2) 0.0272(3) 0.0307(8) Uani 1 1 d . . . H3A H 0.8508 -0.1586 0.0931 0.037 Uiso 1 1 calc R . . H3B H 0.7841 -0.1657 -0.0397 0.037 Uiso 1 1 calc R . . C4 C 0.5601(3) -0.1114(2) -0.0303(3) 0.0279(7) Uani 1 1 d . . . C5 C 0.5200(3) -0.0880(2) -0.1519(3) 0.0302(7) Uani 1 1 d . . . C6 C 0.5642(4) -0.0701(3) -0.3123(3) 0.0520(11) Uani 1 1 d . . . H6 H 0.6206 -0.0703 -0.3479 0.062 Uiso 1 1 calc R . . C7 C 0.4468(4) -0.0504(3) -0.3772(3) 0.0497(10) Uani 1 1 d . . . H7 H 0.4241 -0.0384 -0.4548 0.060 Uiso 1 1 calc R . . C8 C 0.3634(4) -0.0486(3) -0.3253(3) 0.0489(10) Uani 1 1 d . . . H8 H 0.2831 -0.0344 -0.3671 0.059 Uiso 1 1 calc R . . C9 C 0.3991(3) -0.0680(3) -0.2107(3) 0.0399(9) Uani 1 1 d . . . H9 H 0.3438 -0.0677 -0.1738 0.048 Uiso 1 1 calc R . . C10 C 0.5552(3) -0.1475(2) 0.1303(3) 0.0271(7) Uani 1 1 d . . . C11 C 0.5031(3) -0.1664(2) 0.2169(3) 0.0267(7) Uani 1 1 d . . . C12 C 0.3786(3) -0.1736(2) 0.1804(3) 0.0288(7) Uani 1 1 d . . . H12 H 0.3341 -0.1712 0.1024 0.035 Uiso 1 1 calc R . . C13 C 0.3834(3) -0.1893(2) 0.3642(3) 0.0322(8) Uani 1 1 d . . . H13 H 0.3429 -0.1957 0.4149 0.039 Uiso 1 1 calc R . . C14 C 0.5078(3) -0.1856(2) 0.4064(3) 0.0358(8) Uani 1 1 d . . . H14 H 0.5507 -0.1914 0.4844 0.043 Uiso 1 1 calc R . . C15 C 0.5684(3) -0.1733(2) 0.3327(3) 0.0335(8) Uani 1 1 d . . . H15 H 0.6525 -0.1696 0.3605 0.040 Uiso 1 1 calc R . . C16 C 0.9058(3) 0.3212(2) -0.0483(3) 0.0288(8) Uani 1 1 d . . . C17 C 0.9030(3) 0.4244(2) 0.1612(3) 0.0300(8) Uani 1 1 d . . . C18 C 0.9540(3) 0.4594(2) 0.0757(3) 0.0279(7) Uani 1 1 d . . . C19 C 0.9560(3) 0.4130(2) -0.0197(3) 0.0275(7) Uani 1 1 d . . . C20 C 1.0021(3) 0.4547(2) -0.0932(3) 0.0326(8) Uani 1 1 d . . . H20 H 1.0038 0.4238 -0.1567 0.039 Uiso 1 1 calc R . . N1 N 0.8767(2) 0.07712(18) -0.0560(2) 0.0282(6) Uani 1 1 d . . . N2 N 0.8550(3) 0.0191(2) 0.1000(2) 0.0363(7) Uani 1 1 d . . . N3 N 0.8286(2) -0.04178(18) 0.0140(2) 0.0292(6) Uani 1 1 d . . . N4 N 0.6739(2) -0.13053(19) 0.0420(2) 0.0287(6) Uani 1 1 d . . . N5 N 0.6712(2) -0.15416(19) 0.1461(2) 0.0303(6) Uani 1 1 d . . . N6 N 0.4836(2) -0.12110(19) 0.0237(2) 0.0304(6) Uani 1 1 d . . . N7 N 0.6034(3) -0.0891(2) -0.2003(3) 0.0435(8) Uani 1 1 d . . . N8 N 0.3188(2) -0.18399(18) 0.2518(2) 0.0281(6) Uani 1 1 d . . . O1 O 0.9490(2) 0.27754(16) -0.1124(2) 0.0398(6) Uani 1 1 d . . . O2 O 0.8280(2) 0.29332(16) -0.0139(2) 0.0393(6) Uani 1 1 d . . . O3 O 0.9522(2) 0.35688(16) 0.21960(19) 0.0342(6) Uani 1 1 d . . . O4 O 0.8190(3) 0.46510(18) 0.1745(2) 0.0483(7) Uani 1 1 d . . . O1W O 1.1251(3) 0.2298(3) 0.1759(3) 0.0890(12) Uani 1 1 d . . . H1A H 1.1527 0.2821 0.1936 0.134 Uiso 1 1 d R . . H1B H 1.1430 0.1942 0.2329 0.134 Uiso 1 1 d R . . O2W O 1.2158(6) 0.3427(4) -0.0832(6) 0.168(3) Uani 1 1 d . . . H2A H 1.1449 0.3247 -0.0923 0.252 Uiso 1 1 d R . . H2B H 1.2149 0.3989 -0.0824 0.252 Uiso 1 1 d 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 Zn1 0.0305(2) 0.0212(2) 0.0304(2) -0.00373(15) 0.01956(18) -0.00411(15) C1 0.043(2) 0.0339(19) 0.0307(18) -0.0041(16) 0.0166(17) -0.0071(17) C2 0.0283(17) 0.0321(18) 0.0280(16) -0.0009(14) 0.0158(14) -0.0020(15) C3 0.0268(17) 0.0262(17) 0.046(2) 0.0065(16) 0.0211(16) 0.0003(14) C4 0.0292(18) 0.0239(16) 0.0338(18) 0.0023(14) 0.0154(15) -0.0015(14) C5 0.0353(19) 0.0275(17) 0.0306(17) -0.0029(15) 0.0152(16) -0.0045(15) C6 0.061(3) 0.065(3) 0.039(2) -0.003(2) 0.028(2) -0.010(2) C7 0.064(3) 0.049(2) 0.032(2) -0.0001(18) 0.013(2) -0.013(2) C8 0.045(2) 0.050(2) 0.042(2) 0.0035(19) 0.0034(19) -0.007(2) C9 0.037(2) 0.043(2) 0.041(2) 0.0057(17) 0.0143(18) -0.0029(18) C10 0.0252(17) 0.0270(17) 0.0313(18) 0.0006(14) 0.0128(15) -0.0011(14) C11 0.0292(18) 0.0226(16) 0.0321(17) -0.0017(14) 0.0157(15) -0.0007(13) C12 0.0311(18) 0.0336(18) 0.0244(16) -0.0035(14) 0.0130(15) -0.0021(15) C13 0.044(2) 0.0265(17) 0.0336(18) 0.0025(15) 0.0230(17) -0.0005(16) C14 0.044(2) 0.0341(19) 0.0288(18) 0.0030(15) 0.0125(17) 0.0017(17) C15 0.0309(19) 0.0320(19) 0.038(2) 0.0022(15) 0.0125(16) 0.0005(15) C16 0.040(2) 0.0234(17) 0.0235(16) -0.0031(13) 0.0117(16) -0.0069(15) C17 0.039(2) 0.0275(18) 0.0262(17) -0.0056(15) 0.0152(16) -0.0117(16) C18 0.0379(19) 0.0230(16) 0.0261(16) 0.0007(14) 0.0156(15) -0.0063(15) C19 0.0370(18) 0.0210(16) 0.0282(17) -0.0038(14) 0.0164(15) -0.0068(14) C20 0.053(2) 0.0235(17) 0.0283(17) -0.0065(14) 0.0233(17) -0.0093(16) N1 0.0322(15) 0.0277(15) 0.0277(14) 0.0003(12) 0.0145(13) -0.0045(12) N2 0.0410(17) 0.0399(18) 0.0312(15) -0.0011(14) 0.0169(14) -0.0031(14) N3 0.0276(15) 0.0314(15) 0.0332(15) 0.0049(13) 0.0166(13) -0.0010(12) N4 0.0265(15) 0.0316(15) 0.0308(14) 0.0070(12) 0.0137(12) -0.0012(12) N5 0.0293(16) 0.0320(16) 0.0332(15) 0.0063(12) 0.0156(13) -0.0009(12) N6 0.0297(15) 0.0324(16) 0.0340(15) -0.0011(13) 0.0172(13) -0.0007(13) N7 0.0444(19) 0.055(2) 0.0382(17) 0.0019(15) 0.0230(16) -0.0028(16) N8 0.0311(15) 0.0281(15) 0.0308(15) -0.0008(12) 0.0182(13) 0.0000(12) O1 0.0521(15) 0.0291(13) 0.0486(14) -0.0157(12) 0.0306(13) -0.0146(12) O2 0.0520(16) 0.0309(13) 0.0444(14) -0.0078(12) 0.0288(13) -0.0173(12) O3 0.0429(14) 0.0336(13) 0.0322(12) 0.0084(11) 0.0210(12) -0.0002(11) O4 0.0614(18) 0.0429(16) 0.0597(17) 0.0077(13) 0.0447(16) 0.0071(14) O1W 0.074(2) 0.105(3) 0.081(3) -0.023(2) 0.021(2) 0.002(2) O2W 0.129(5) 0.153(6) 0.212(7) -0.002(5) 0.049(5) 0.035(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O1 1.931(2) . ? Zn1 O3 1.959(2) 4_565 ? Zn1 N1 2.040(3) . ? Zn1 N8 2.050(3) 3_655 ? C1 N2 1.303(4) . ? C1 N1 1.371(4) . ? C1 H1 0.9300 . ? C2 N1 1.325(4) . ? C2 N3 1.327(4) . ? C2 H2 0.9300 . ? C3 N3 1.450(4) . ? C3 N4 1.459(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N6 1.322(4) . ? C4 N4 1.357(4) . ? C4 C5 1.470(4) . ? C5 N7 1.336(4) . ? C5 C9 1.387(5) . ? C6 N7 1.343(5) . ? C6 C7 1.367(6) . ? C6 H6 0.9300 . ? C7 C8 1.368(6) . ? C7 H7 0.9300 . ? C8 C9 1.376(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N5 1.319(4) . ? C10 N6 1.359(4) . ? C10 C11 1.461(4) . ? C11 C12 1.382(5) . ? C11 C15 1.382(5) . ? C12 N8 1.339(4) . ? C12 H12 0.9300 . ? C13 N8 1.343(5) . ? C13 C14 1.376(5) . ? C13 H13 0.9300 . ? C14 C15 1.375(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O2 1.227(4) . ? C16 O1 1.282(4) . ? C16 C19 1.500(4) . ? C17 O4 1.233(4) . ? C17 O3 1.268(4) . ? C17 C18 1.506(4) . ? C18 C20 1.386(4) 3_765 ? C18 C19 1.396(4) . ? C19 C20 1.383(4) . ? C20 C18 1.386(4) 3_765 ? C20 H20 0.9300 . ? N2 N3 1.366(4) . ? N4 N5 1.368(4) . ? N8 Zn1 2.050(3) 3_655 ? O3 Zn1 1.959(2) 4_566 ? O1W H1A 0.8528 . ? O1W H1B 0.8571 . ? O2W H2A 0.8500 . ? O2W H2B 0.8500 . ? 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 O1 Zn1 O3 98.10(10) . 4_565 ? O1 Zn1 N1 111.95(11) . . ? O3 Zn1 N1 116.52(10) 4_565 . ? O1 Zn1 N8 113.65(11) . 3_655 ? O3 Zn1 N8 116.80(10) 4_565 3_655 ? N1 Zn1 N8 100.52(11) . 3_655 ? N2 C1 N1 114.3(3) . . ? N2 C1 H1 122.9 . . ? N1 C1 H1 122.9 . . ? N1 C2 N3 109.4(3) . . ? N1 C2 H2 125.3 . . ? N3 C2 H2 125.3 . . ? N3 C3 N4 111.0(3) . . ? N3 C3 H3A 109.4 . . ? N4 C3 H3A 109.4 . . ? N3 C3 H3B 109.4 . . ? N4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N6 C4 N4 109.5(3) . . ? N6 C4 C5 122.5(3) . . ? N4 C4 C5 127.9(3) . . ? N7 C5 C9 123.6(3) . . ? N7 C5 C4 117.2(3) . . ? C9 C5 C4 119.2(3) . . ? N7 C6 C7 124.2(4) . . ? N7 C6 H6 117.9 . . ? C7 C6 H6 117.9 . . ? C6 C7 C8 118.3(4) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C5 118.0(3) . . ? C8 C9 H9 121.0 . . ? C5 C9 H9 121.0 . . ? N5 C10 N6 114.5(3) . . ? N5 C10 C11 124.8(3) . . ? N6 C10 C11 120.6(3) . . ? C12 C11 C15 117.8(3) . . ? C12 C11 C10 117.2(3) . . ? C15 C11 C10 124.9(3) . . ? N8 C12 C11 123.2(3) . . ? N8 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? N8 C13 C14 121.7(3) . . ? N8 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C11 119.3(3) . . ? C14 C15 H15 120.3 . . ? C11 C15 H15 120.3 . . ? O2 C16 O1 124.6(3) . . ? O2 C16 C19 121.0(3) . . ? O1 C16 C19 114.3(3) . . ? O4 C17 O3 123.1(3) . . ? O4 C17 C18 118.4(3) . . ? O3 C17 C18 118.4(3) . . ? C20 C18 C19 118.9(3) 3_765 . ? C20 C18 C17 116.1(3) 3_765 . ? C19 C18 C17 124.9(3) . . ? C20 C19 C18 118.6(3) . . ? C20 C19 C16 118.6(3) . . ? C18 C19 C16 122.7(3) . . ? C19 C20 C18 122.5(3) . 3_765 ? C19 C20 H20 118.8 . . ? C18 C20 H20 118.8 3_765 . ? C2 N1 C1 103.3(3) . . ? C2 N1 Zn1 124.6(2) . . ? C1 N1 Zn1 129.2(2) . . ? C1 N2 N3 102.5(3) . . ? C2 N3 N2 110.5(3) . . ? C2 N3 C3 127.7(3) . . ? N2 N3 C3 121.7(3) . . ? C4 N4 N5 109.4(2) . . ? C4 N4 C3 132.4(3) . . ? N5 N4 C3 118.2(3) . . ? C10 N5 N4 102.8(3) . . ? C4 N6 C10 103.8(3) . . ? C5 N7 C6 116.2(3) . . ? C12 N8 C13 118.3(3) . . ? C12 N8 Zn1 114.8(2) . 3_655 ? C13 N8 Zn1 126.1(2) . 3_655 ? C16 O1 Zn1 116.2(2) . . ? C17 O3 Zn1 107.7(2) . 4_566 ? H1A O1W H1B 114.0 . . ? H2A O2W H2B 107.7 . . ? 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 N6 C4 C5 N7 -173.1(3) . . . . ? N4 C4 C5 N7 3.2(5) . . . . ? N6 C4 C5 C9 5.6(5) . . . . ? N4 C4 C5 C9 -178.1(3) . . . . ? N7 C6 C7 C8 0.9(7) . . . . ? C6 C7 C8 C9 -1.1(6) . . . . ? C7 C8 C9 C5 0.5(6) . . . . ? N7 C5 C9 C8 0.3(6) . . . . ? C4 C5 C9 C8 -178.3(3) . . . . ? N5 C10 C11 C12 -167.2(3) . . . . ? N6 C10 C11 C12 12.7(5) . . . . ? N5 C10 C11 C15 16.0(5) . . . . ? N6 C10 C11 C15 -164.1(3) . . . . ? C15 C11 C12 N8 2.3(5) . . . . ? C10 C11 C12 N8 -174.8(3) . . . . ? N8 C13 C14 C15 2.1(5) . . . . ? C13 C14 C15 C11 -1.1(5) . . . . ? C12 C11 C15 C14 -1.0(5) . . . . ? C10 C11 C15 C14 175.8(3) . . . . ? O4 C17 C18 C20 57.7(5) . . . 3_765 ? O3 C17 C18 C20 -119.2(4) . . . 3_765 ? O4 C17 C18 C19 -119.9(4) . . . . ? O3 C17 C18 C19 63.2(5) . . . . ? C20 C18 C19 C20 0.3(6) 3_765 . . . ? C17 C18 C19 C20 177.8(3) . . . . ? C20 C18 C19 C16 -177.4(3) 3_765 . . . ? C17 C18 C19 C16 0.2(5) . . . . ? O2 C16 C19 C20 -153.7(3) . . . . ? O1 C16 C19 C20 24.6(5) . . . . ? O2 C16 C19 C18 23.9(5) . . . . ? O1 C16 C19 C18 -157.7(3) . . . . ? C18 C19 C20 C18 -0.3(6) . . . 3_765 ? C16 C19 C20 C18 177.5(3) . . . 3_765 ? N3 C2 N1 C1 0.0(4) . . . . ? N3 C2 N1 Zn1 -162.3(2) . . . . ? N2 C1 N1 C2 0.3(4) . . . . ? N2 C1 N1 Zn1 161.4(2) . . . . ? O1 Zn1 N1 C2 -170.4(2) . . . . ? O3 Zn1 N1 C2 -58.6(3) 4_565 . . . ? N8 Zn1 N1 C2 68.7(3) 3_655 . . . ? O1 Zn1 N1 C1 32.1(3) . . . . ? O3 Zn1 N1 C1 143.9(3) 4_565 . . . ? N8 Zn1 N1 C1 -88.9(3) 3_655 . . . ? N1 C1 N2 N3 -0.4(4) . . . . ? N1 C2 N3 N2 -0.3(4) . . . . ? N1 C2 N3 C3 179.2(3) . . . . ? C1 N2 N3 C2 0.4(4) . . . . ? C1 N2 N3 C3 -179.1(3) . . . . ? N4 C3 N3 C2 -114.5(3) . . . . ? N4 C3 N3 N2 64.9(4) . . . . ? N6 C4 N4 N5 0.5(4) . . . . ? C5 C4 N4 N5 -176.2(3) . . . . ? N6 C4 N4 C3 179.7(3) . . . . ? C5 C4 N4 C3 2.9(6) . . . . ? N3 C3 N4 C4 69.6(5) . . . . ? N3 C3 N4 N5 -111.3(3) . . . . ? N6 C10 N5 N4 -0.2(4) . . . . ? C11 C10 N5 N4 179.7(3) . . . . ? C4 N4 N5 C10 -0.2(4) . . . . ? C3 N4 N5 C10 -179.5(3) . . . . ? N4 C4 N6 C10 -0.6(4) . . . . ? C5 C4 N6 C10 176.4(3) . . . . ? N5 C10 N6 C4 0.5(4) . . . . ? C11 C10 N6 C4 -179.4(3) . . . . ? C9 C5 N7 C6 -0.6(6) . . . . ? C4 C5 N7 C6 178.1(3) . . . . ? C7 C6 N7 C5 -0.1(6) . . . . ? C11 C12 N8 C13 -1.3(5) . . . . ? C11 C12 N8 Zn1 169.0(3) . . . 3_655 ? C14 C13 N8 C12 -0.9(5) . . . . ? C14 C13 N8 Zn1 -170.1(3) . . . 3_655 ? O2 C16 O1 Zn1 10.7(5) . . . . ? C19 C16 O1 Zn1 -167.6(2) . . . . ? O3 Zn1 O1 C16 172.1(2) 4_565 . . . ? N1 Zn1 O1 C16 -65.0(3) . . . . ? N8 Zn1 O1 C16 48.1(3) 3_655 . . . ? O4 C17 O3 Zn1 2.7(4) . . . 4_566 ? C18 C17 O3 Zn1 179.4(2) . . . 4_566 ? 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 O1W H1A N5 0.85 2.51 3.160(5) 133.9 2_755 O1W H1B O2W 0.86 2.22 3.025(8) 155.4 4_566 O2W H2A O1 0.85 2.35 3.203(7) 178.2 . O2W H2B O4 0.85 2.32 3.093(7) 151.6 3_765 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.449 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.076 #========================================================== data_compound-6 _database_code_depnum_ccdc_archive 'CCDC 892070' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H18 N8 O5 Zn' _chemical_formula_sum 'C23 H18 N8 O5 Zn' _chemical_formula_weight 551.82 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 triclinic _symmetry_space_group_name_H-M p-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7186(5) _cell_length_b 11.4928(6) _cell_length_c 11.6881(6) _cell_angle_alpha 63.618(5) _cell_angle_beta 80.197(5) _cell_angle_gamma 81.893(4) _cell_volume 1149.29(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2095 _cell_measurement_theta_min 2.7975 _cell_measurement_theta_max 29.0925 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 1.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7743 _exptl_absorpt_correction_T_max 0.8149 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7529 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4189 _reflns_number_gt 2988 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0494P)^2^+0.0000P] 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_number_reflns 4189 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1252 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Zn1 Zn 0.59917(5) 0.23428(4) -0.13121(5) 0.03612(19) Uani 1 1 d . . . C1 C 0.4202(4) 0.4851(4) -0.2243(4) 0.0429(11) Uani 1 1 d . . . H1 H 0.3660 0.4441 -0.1457 0.052 Uiso 1 1 calc R . . C2 C 0.3836(4) 0.6125(4) -0.3031(5) 0.0462(12) Uani 1 1 d . . . H2 H 0.3052 0.6561 -0.2779 0.055 Uiso 1 1 calc R . . C3 C 0.4629(4) 0.6755(4) -0.4194(4) 0.0422(11) Uani 1 1 d . . . H3 H 0.4399 0.7620 -0.4734 0.051 Uiso 1 1 calc R . . C4 C 0.5787(4) 0.6066(4) -0.4544(4) 0.0330(10) Uani 1 1 d . . . C5 C 0.6081(4) 0.4792(4) -0.3695(4) 0.0346(10) Uani 1 1 d . . . H5 H 0.6861 0.4335 -0.3923 0.041 Uiso 1 1 calc R . . C6 C 0.6697(4) 0.6692(4) -0.5756(4) 0.0339(10) Uani 1 1 d . . . C7 C 0.7730(4) 0.9325(4) -0.8615(4) 0.0387(11) Uani 1 1 d . . . H7A H 0.8353 0.9210 -0.9305 0.046 Uiso 1 1 calc R . . H7B H 0.6817 0.9654 -0.8909 0.046 Uiso 1 1 calc R . . C8 C 0.7569(5) 1.1031(5) -0.7808(5) 0.0477(12) Uani 1 1 d . . . H8 H 0.6610 1.1049 -0.7548 0.057 Uiso 1 1 calc R . . C9 C 0.9668(5) 1.1373(5) -0.8195(5) 0.0555(13) Uani 1 1 d . . . H9 H 1.0495 1.1725 -0.8249 0.067 Uiso 1 1 calc R . . C10 C 0.8364(4) 0.6929(4) -0.7223(4) 0.0351(10) Uani 1 1 d . . . C11 C 0.9657(4) 0.6706(4) -0.7994(4) 0.0352(10) Uani 1 1 d . . . C12 C 0.9774(4) 0.5733(5) -0.8403(5) 0.0485(12) Uani 1 1 d . . . H12 H 0.9025 0.5235 -0.8234 0.058 Uiso 1 1 calc R . . C13 C 1.1017(5) 0.5514(5) -0.9062(5) 0.0542(13) Uani 1 1 d . . . H13 H 1.1103 0.4894 -0.9382 0.065 Uiso 1 1 calc R . . C14 C 1.2125(4) 0.6212(4) -0.9244(4) 0.0430(11) Uani 1 1 d . . . H14 H 1.2959 0.6057 -0.9696 0.052 Uiso 1 1 calc R . . C15 C 1.0826(4) 0.7370(4) -0.8209(4) 0.0368(10) Uani 1 1 d . . . H15 H 1.0753 0.8023 -0.7932 0.044 Uiso 1 1 calc R . . C16 C 0.3902(4) 0.1866(4) 0.0692(4) 0.0343(10) Uani 1 1 d . . . C17 C 0.3237(4) -0.0906(4) 0.2534(4) 0.0377(10) Uani 1 1 d . . . C18 C 0.2918(4) 0.0197(4) 0.2909(4) 0.0329(10) Uani 1 1 d . . . C19 C 0.2199(4) -0.0032(5) 0.4123(4) 0.0453(11) Uani 1 1 d . . . H19 H 0.1974 -0.0873 0.4695 0.054 Uiso 1 1 calc R . . C20 C 0.1817(5) 0.0966(5) 0.4486(5) 0.0537(13) Uani 1 1 d . . . H20 H 0.1316 0.0803 0.5288 0.064 Uiso 1 1 calc R . . C21 C 0.2180(5) 0.2205(5) 0.3659(5) 0.0509(13) Uani 1 1 d . . . H21 H 0.1919 0.2881 0.3902 0.061 Uiso 1 1 calc R . . C22 C 0.2924(4) 0.2450(4) 0.2475(4) 0.0452(12) Uani 1 1 d . . . H22 H 0.3199 0.3284 0.1937 0.054 Uiso 1 1 calc R . . C23 C 0.3271(4) 0.1455(4) 0.2074(4) 0.0309(9) Uani 1 1 d . . . N1 N 0.5319(3) 0.4173(3) -0.2568(3) 0.0344(8) Uani 1 1 d . . . N2 N 0.7811(3) 0.6021(3) -0.6133(3) 0.0357(8) Uani 1 1 d . . . N3 N 0.6522(3) 0.7928(3) -0.6558(3) 0.0361(8) Uani 1 1 d . . . N4 N 0.7608(3) 0.8071(3) -0.7495(3) 0.0342(8) Uani 1 1 d . . . N5 N 0.8259(3) 1.0259(3) -0.8326(3) 0.0354(8) Uani 1 1 d . . . N6 N 0.9645(4) 1.0466(3) -0.8582(4) 0.0490(10) Uani 1 1 d . . . N7 N 0.8429(4) 1.1766(4) -0.7714(4) 0.0561(11) Uani 1 1 d . . . N8 N 1.2060(3) 0.7114(3) -0.8798(3) 0.0374(9) Uani 1 1 d . . . O1 O 0.3139(3) 0.2184(3) -0.0148(3) 0.0485(8) Uani 1 1 d . . . O2 O 0.5233(3) 0.1988(3) 0.0463(3) 0.0427(8) Uani 1 1 d . . . O3 O 0.3941(3) -0.0696(3) 0.1447(3) 0.0452(8) Uani 1 1 d . . . O4 O 0.2801(3) -0.1989(3) 0.3269(3) 0.0523(9) Uani 1 1 d . . . O1W O 0.0528(4) -0.3411(4) 0.5011(5) 0.1105(17) Uani 1 1 d . . . H1A H 0.0973 -0.3052 0.4263 0.166 Uiso 1 1 d R . . H1B H 0.0976 -0.4131 0.5424 0.166 Uiso 1 1 d 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 Zn1 0.0314(3) 0.0330(3) 0.0391(3) -0.0128(2) 0.0023(2) -0.0047(2) C1 0.034(2) 0.042(3) 0.048(3) -0.019(2) 0.009(2) -0.007(2) C2 0.035(2) 0.042(3) 0.055(3) -0.020(2) 0.005(2) 0.004(2) C3 0.035(2) 0.036(2) 0.047(3) -0.011(2) -0.006(2) -0.0030(19) C4 0.025(2) 0.035(2) 0.041(3) -0.019(2) 0.0019(19) -0.0052(17) C5 0.028(2) 0.033(2) 0.036(3) -0.010(2) 0.0013(19) -0.0024(17) C6 0.025(2) 0.037(2) 0.039(3) -0.016(2) -0.0040(19) -0.0026(18) C7 0.038(2) 0.037(2) 0.033(3) -0.009(2) 0.000(2) -0.0048(19) C8 0.038(3) 0.052(3) 0.054(3) -0.025(3) -0.004(2) -0.001(2) C9 0.043(3) 0.045(3) 0.080(4) -0.024(3) -0.017(3) -0.006(2) C10 0.028(2) 0.037(2) 0.040(3) -0.017(2) 0.0002(19) -0.0083(19) C11 0.032(2) 0.038(2) 0.032(2) -0.011(2) -0.0019(19) -0.0056(18) C12 0.033(3) 0.059(3) 0.058(3) -0.028(3) 0.001(2) -0.015(2) C13 0.041(3) 0.069(3) 0.069(4) -0.046(3) -0.003(3) -0.005(2) C14 0.032(2) 0.052(3) 0.044(3) -0.023(2) -0.001(2) 0.000(2) C15 0.033(2) 0.031(2) 0.042(3) -0.013(2) -0.001(2) -0.0021(18) C16 0.036(2) 0.028(2) 0.037(3) -0.015(2) 0.004(2) -0.0042(18) C17 0.031(2) 0.036(3) 0.040(3) -0.009(2) -0.011(2) -0.0014(19) C18 0.030(2) 0.033(2) 0.032(2) -0.011(2) -0.0032(18) -0.0001(18) C19 0.043(3) 0.052(3) 0.037(3) -0.015(2) 0.000(2) -0.009(2) C20 0.051(3) 0.073(4) 0.042(3) -0.032(3) 0.006(2) -0.004(3) C21 0.051(3) 0.058(3) 0.056(3) -0.037(3) -0.003(2) -0.005(2) C22 0.042(3) 0.042(3) 0.054(3) -0.023(2) 0.001(2) -0.009(2) C23 0.021(2) 0.033(2) 0.040(2) -0.016(2) -0.0041(18) -0.0017(16) N1 0.0289(19) 0.0349(19) 0.035(2) -0.0116(17) 0.0025(16) -0.0071(15) N2 0.0289(19) 0.034(2) 0.040(2) -0.0136(18) 0.0001(16) -0.0055(15) N3 0.0325(19) 0.036(2) 0.033(2) -0.0103(18) 0.0008(16) -0.0049(15) N4 0.0322(19) 0.0296(19) 0.032(2) -0.0063(16) 0.0036(16) -0.0063(15) N5 0.0314(19) 0.0311(19) 0.039(2) -0.0102(17) -0.0005(16) -0.0072(15) N6 0.033(2) 0.042(2) 0.072(3) -0.026(2) -0.0002(19) -0.0045(17) N7 0.052(3) 0.053(3) 0.071(3) -0.035(2) -0.016(2) 0.007(2) N8 0.0268(19) 0.038(2) 0.044(2) -0.0177(18) 0.0053(16) -0.0058(15) O1 0.0493(19) 0.051(2) 0.040(2) -0.0102(16) -0.0118(16) -0.0119(15) O2 0.0287(16) 0.059(2) 0.0401(18) -0.0223(16) 0.0072(13) -0.0140(14) O3 0.0524(19) 0.0380(17) 0.0436(19) -0.0201(16) 0.0075(16) -0.0056(14) O4 0.058(2) 0.0355(18) 0.058(2) -0.0155(17) 0.0024(17) -0.0123(15) O1W 0.083(3) 0.089(3) 0.117(4) -0.021(3) 0.022(3) 0.005(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O2 1.956(3) . ? Zn1 O3 1.959(3) 2_655 ? Zn1 N1 2.050(3) . ? Zn1 N8 2.116(3) 2_764 ? Zn1 C17 2.590(4) 2_655 ? C1 N1 1.346(5) . ? C1 C2 1.373(6) . ? C1 H1 0.9300 . ? C2 C3 1.376(6) . ? C2 H2 0.9300 . ? C3 C4 1.393(5) . ? C3 H3 0.9300 . ? C4 C5 1.378(6) . ? C4 C6 1.468(5) . ? C5 N1 1.332(5) . ? C5 H5 0.9300 . ? C6 N3 1.315(5) . ? C6 N2 1.365(5) . ? C7 N5 1.439(5) . ? C7 N4 1.457(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N7 1.318(6) . ? C8 N5 1.333(5) . ? C8 H8 0.9300 . ? C9 N6 1.313(6) . ? C9 N7 1.346(6) . ? C9 H9 0.9300 . ? C10 N2 1.321(5) . ? C10 N4 1.342(5) . ? C10 C11 1.478(5) . ? C11 C12 1.383(6) . ? C11 C15 1.383(5) . ? C12 C13 1.372(6) . ? C12 H12 0.9300 . ? C13 C14 1.365(6) . ? C13 H13 0.9300 . ? C14 N8 1.342(5) . ? C14 H14 0.9300 . ? C15 N8 1.341(5) . ? C15 H15 0.9300 . ? C16 O1 1.225(5) . ? C16 O2 1.291(5) . ? C16 C23 1.508(6) . ? C17 O4 1.242(5) . ? C17 O3 1.272(5) . ? C17 C18 1.495(6) . ? C17 Zn1 2.590(4) 2_655 ? C18 C23 1.390(5) . ? C18 C19 1.398(5) . ? C19 C20 1.375(6) . ? C19 H19 0.9300 . ? C20 C21 1.374(6) . ? C20 H20 0.9300 . ? C21 C22 1.373(6) . ? C21 H21 0.9300 . ? C22 C23 1.398(5) . ? C22 H22 0.9300 . ? N3 N4 1.355(4) . ? N5 N6 1.360(4) . ? N8 Zn1 2.116(3) 2_764 ? O3 Zn1 1.959(3) 2_655 ? O1W H1A 0.8500 . ? O1W H1B 0.8500 . ? 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 O2 Zn1 O3 106.44(12) . 2_655 ? O2 Zn1 N1 111.09(12) . . ? O3 Zn1 N1 128.71(13) 2_655 . ? O2 Zn1 N8 94.88(13) . 2_764 ? O3 Zn1 N8 115.40(13) 2_655 2_764 ? N1 Zn1 N8 95.06(13) . 2_764 ? O2 Zn1 C17 134.22(13) . 2_655 ? O3 Zn1 C17 28.38(12) 2_655 2_655 ? N1 Zn1 C17 109.59(13) . 2_655 ? N8 Zn1 C17 101.61(13) 2_764 2_655 ? N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 119.9(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 118.4(4) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 117.9(4) . . ? C5 C4 C6 121.0(3) . . ? C3 C4 C6 121.1(4) . . ? N1 C5 C4 124.1(4) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? N3 C6 N2 114.7(3) . . ? N3 C6 C4 123.5(3) . . ? N2 C6 C4 121.9(4) . . ? N5 C7 N4 111.6(3) . . ? N5 C7 H7A 109.3 . . ? N4 C7 H7A 109.3 . . ? N5 C7 H7B 109.3 . . ? N4 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? N7 C8 N5 110.8(4) . . ? N7 C8 H8 124.6 . . ? N5 C8 H8 124.6 . . ? N6 C9 N7 116.4(4) . . ? N6 C9 H9 121.8 . . ? N7 C9 H9 121.8 . . ? N2 C10 N4 110.1(3) . . ? N2 C10 C11 124.1(4) . . ? N4 C10 C11 125.7(4) . . ? C12 C11 C15 118.3(4) . . ? C12 C11 C10 120.6(4) . . ? C15 C11 C10 120.8(4) . . ? C13 C12 C11 118.8(4) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C14 C13 C12 119.7(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? N8 C14 C13 122.6(4) . . ? N8 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? N8 C15 C11 122.9(4) . . ? N8 C15 H15 118.5 . . ? C11 C15 H15 118.5 . . ? O1 C16 O2 123.8(4) . . ? O1 C16 C23 119.9(4) . . ? O2 C16 C23 115.9(4) . . ? O4 C17 O3 121.7(4) . . ? O4 C17 C18 120.0(4) . . ? O3 C17 C18 118.3(4) . . ? O4 C17 Zn1 74.7(3) . 2_655 ? O3 C17 Zn1 47.1(2) . 2_655 ? C18 C17 Zn1 165.1(3) . 2_655 ? C23 C18 C19 118.8(4) . . ? C23 C18 C17 122.2(3) . . ? C19 C18 C17 119.0(4) . . ? C20 C19 C18 121.1(4) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 119.7(4) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.4(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C18 C23 C22 119.5(4) . . ? C18 C23 C16 124.2(3) . . ? C22 C23 C16 116.1(4) . . ? C5 N1 C1 117.3(3) . . ? C5 N1 Zn1 120.0(3) . . ? C1 N1 Zn1 122.3(3) . . ? C10 N2 C6 102.7(3) . . ? C6 N3 N4 102.7(3) . . ? C10 N4 N3 109.8(3) . . ? C10 N4 C7 131.0(3) . . ? N3 N4 C7 119.0(3) . . ? C8 N5 N6 109.7(4) . . ? C8 N5 C7 129.2(4) . . ? N6 N5 C7 121.1(3) . . ? C9 N6 N5 101.4(3) . . ? C8 N7 C9 101.8(4) . . ? C15 N8 C14 117.6(4) . . ? C15 N8 Zn1 124.9(3) . 2_764 ? C14 N8 Zn1 115.8(3) . 2_764 ? C16 O2 Zn1 113.0(3) . . ? C17 O3 Zn1 104.6(3) . 2_655 ? H1A O1W H1B 107.7 . . ? 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 -0.5(7) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C2 C3 C4 C5 -0.8(6) . . . . ? C2 C3 C4 C6 -178.4(4) . . . . ? C3 C4 C5 N1 0.9(7) . . . . ? C6 C4 C5 N1 178.5(4) . . . . ? C5 C4 C6 N3 -175.0(4) . . . . ? C3 C4 C6 N3 2.5(6) . . . . ? C5 C4 C6 N2 4.5(6) . . . . ? C3 C4 C6 N2 -178.0(4) . . . . ? N2 C10 C11 C12 55.2(6) . . . . ? N4 C10 C11 C12 -126.9(5) . . . . ? N2 C10 C11 C15 -118.0(5) . . . . ? N4 C10 C11 C15 59.9(6) . . . . ? C15 C11 C12 C13 -3.5(7) . . . . ? C10 C11 C12 C13 -176.8(4) . . . . ? C11 C12 C13 C14 3.2(7) . . . . ? C12 C13 C14 N8 0.3(8) . . . . ? C12 C11 C15 N8 0.3(6) . . . . ? C10 C11 C15 N8 173.6(4) . . . . ? O4 C17 C18 C23 -174.0(4) . . . . ? O3 C17 C18 C23 5.0(6) . . . . ? Zn1 C17 C18 C23 -4.6(13) 2_655 . . . ? O4 C17 C18 C19 3.7(6) . . . . ? O3 C17 C18 C19 -177.2(4) . . . . ? Zn1 C17 C18 C19 173.1(9) 2_655 . . . ? C23 C18 C19 C20 1.3(6) . . . . ? C17 C18 C19 C20 -176.5(4) . . . . ? C18 C19 C20 C21 -1.8(7) . . . . ? C19 C20 C21 C22 -0.3(7) . . . . ? C20 C21 C22 C23 2.8(7) . . . . ? C19 C18 C23 C22 1.2(6) . . . . ? C17 C18 C23 C22 179.0(4) . . . . ? C19 C18 C23 C16 -173.0(4) . . . . ? C17 C18 C23 C16 4.8(6) . . . . ? C21 C22 C23 C18 -3.2(6) . . . . ? C21 C22 C23 C16 171.4(4) . . . . ? O1 C16 C23 C18 85.3(5) . . . . ? O2 C16 C23 C18 -101.9(5) . . . . ? O1 C16 C23 C22 -89.1(5) . . . . ? O2 C16 C23 C22 83.7(5) . . . . ? C4 C5 N1 C1 -0.8(6) . . . . ? C4 C5 N1 Zn1 -173.5(3) . . . . ? C2 C1 N1 C5 0.6(6) . . . . ? C2 C1 N1 Zn1 173.1(4) . . . . ? O2 Zn1 N1 C5 154.2(3) . . . . ? O3 Zn1 N1 C5 -71.5(3) 2_655 . . . ? N8 Zn1 N1 C5 57.0(3) 2_764 . . . ? C17 Zn1 N1 C5 -47.2(3) 2_655 . . . ? O2 Zn1 N1 C1 -18.1(4) . . . . ? O3 Zn1 N1 C1 116.2(3) 2_655 . . . ? N8 Zn1 N1 C1 -115.3(3) 2_764 . . . ? C17 Zn1 N1 C1 140.5(3) 2_655 . . . ? N4 C10 N2 C6 -1.2(4) . . . . ? C11 C10 N2 C6 177.0(4) . . . . ? N3 C6 N2 C10 1.7(5) . . . . ? C4 C6 N2 C10 -177.9(4) . . . . ? N2 C6 N3 N4 -1.4(5) . . . . ? C4 C6 N3 N4 178.1(4) . . . . ? N2 C10 N4 N3 0.4(5) . . . . ? C11 C10 N4 N3 -177.8(4) . . . . ? N2 C10 N4 C7 -175.2(4) . . . . ? C11 C10 N4 C7 6.6(7) . . . . ? C6 N3 N4 C10 0.6(4) . . . . ? C6 N3 N4 C7 176.8(4) . . . . ? N5 C7 N4 C10 -107.9(5) . . . . ? N5 C7 N4 N3 76.8(4) . . . . ? N7 C8 N5 N6 0.7(5) . . . . ? N7 C8 N5 C7 -179.1(4) . . . . ? N4 C7 N5 C8 -84.5(5) . . . . ? N4 C7 N5 N6 95.7(4) . . . . ? N7 C9 N6 N5 0.0(5) . . . . ? C8 N5 N6 C9 -0.4(5) . . . . ? C7 N5 N6 C9 179.4(4) . . . . ? N5 C8 N7 C9 -0.6(5) . . . . ? N6 C9 N7 C8 0.3(6) . . . . ? C11 C15 N8 C14 3.1(6) . . . . ? C11 C15 N8 Zn1 -161.1(3) . . . 2_764 ? C13 C14 N8 C15 -3.5(7) . . . . ? C13 C14 N8 Zn1 162.2(4) . . . 2_764 ? O1 C16 O2 Zn1 -13.6(5) . . . . ? C23 C16 O2 Zn1 173.9(2) . . . . ? O3 Zn1 O2 C16 -74.8(3) 2_655 . . . ? N1 Zn1 O2 C16 69.6(3) . . . . ? N8 Zn1 O2 C16 166.9(3) 2_764 . . . ? C17 Zn1 O2 C16 -81.7(3) 2_655 . . . ? O4 C17 O3 Zn1 2.4(5) . . . 2_655 ? C18 C17 O3 Zn1 -176.6(3) . . . 2_655 ? 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 O1W H1A O4 0.85 2.15 2.867(5) 141.2 . O1W H1B N2 0.85 2.19 3.030(5) 168.8 2_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.476 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.074 #========================================================== data_compound-7 _database_code_depnum_ccdc_archive 'CCDC 892071' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 N8 O6 Zn' _chemical_formula_sum 'C23 H20 N8 O6 Zn' _chemical_formula_weight 569.84 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 p21/n _symmetry_space_group_name_hall '-P 2yn' 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' _cell_length_a 9.8552(3) _cell_length_b 23.1468(8) _cell_length_c 10.2245(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.033(3) _cell_angle_gamma 90.00 _cell_volume 2309.49(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2058 _cell_measurement_theta_min 3.0889 _cell_measurement_theta_max 29.0840 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7821 _exptl_absorpt_correction_T_max 0.8065 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9048 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4215 _reflns_number_gt 3080 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2006)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0296P)^2^+0.4126P] 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_number_reflns 4215 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _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 Zn1 Zn -0.15598(4) 0.072748(16) 0.79158(4) 0.03025(13) Uani 1 1 d . . . C1 C 0.1524(3) 0.07943(13) 0.7504(3) 0.0333(8) Uani 1 1 d . . . H1 H 0.1320 0.0650 0.6651 0.040 Uiso 1 1 calc R . . C2 C 0.1413(3) 0.10799(16) 0.9417(4) 0.0459(10) Uani 1 1 d . . . H2 H 0.1055 0.1168 1.0188 0.055 Uiso 1 1 calc R . . C3 C 0.4031(3) 0.09900(13) 0.7494(3) 0.0335(8) Uani 1 1 d . . . H3A H 0.4030 0.0695 0.6821 0.040 Uiso 1 1 calc R . . H3B H 0.4793 0.0913 0.8181 0.040 Uiso 1 1 calc R . . C4 C 0.4585(3) 0.20834(14) 0.7429(4) 0.0368(8) Uani 1 1 d . . . C5 C 0.5055(3) 0.22473(14) 0.8804(4) 0.0392(9) Uani 1 1 d . . . C6 C 0.5114(4) 0.28347(16) 0.9098(5) 0.0543(11) Uani 1 1 d . . . H6 H 0.4798 0.3093 0.8427 0.065 Uiso 1 1 calc R . . C7 C 0.6030(4) 0.26778(18) 1.1246(5) 0.0571(11) Uani 1 1 d . . . H7 H 0.6357 0.2821 1.2081 0.068 Uiso 1 1 calc R . . C8 C 0.6013(3) 0.20907(16) 1.1053(4) 0.0495(10) Uani 1 1 d . . . H8 H 0.6327 0.1843 1.1745 0.059 Uiso 1 1 calc R . . C9 C 0.5525(3) 0.18732(15) 0.9825(4) 0.0424(9) Uani 1 1 d . . . H9 H 0.5512 0.1476 0.9680 0.051 Uiso 1 1 calc R . . C10 C 0.3996(3) 0.21573(15) 0.5364(4) 0.0387(9) Uani 1 1 d . . . C11 C 0.3639(3) 0.24293(15) 0.4059(4) 0.0395(9) Uani 1 1 d . . . C12 C 0.3634(3) 0.30271(15) 0.3978(4) 0.0406(9) Uani 1 1 d . . . H12 H 0.3909 0.3237 0.4745 0.049 Uiso 1 1 calc R . . C13 C 0.2848(3) 0.30084(16) 0.1774(4) 0.0435(9) Uani 1 1 d . . . H13 H 0.2567 0.3204 0.0989 0.052 Uiso 1 1 calc R . . C14 C 0.2824(4) 0.24130(16) 0.1761(4) 0.0483(10) Uani 1 1 d . . . H14 H 0.2540 0.2214 0.0981 0.058 Uiso 1 1 calc R . . C15 C 0.3224(4) 0.21179(16) 0.2913(4) 0.0492(10) Uani 1 1 d . . . H15 H 0.3218 0.1716 0.2927 0.059 Uiso 1 1 calc R . . C16 C -0.2277(4) 0.06477(13) 0.5307(3) 0.0393(9) Uani 1 1 d . . . C17 C -0.2256(3) 0.06389(13) 0.0407(3) 0.0317(8) Uani 1 1 d . . . C18 C -0.3038(3) 0.05872(12) 0.1568(3) 0.0247(7) Uani 1 1 d . . . C19 C -0.2352(3) 0.06288(12) 0.2841(3) 0.0297(7) Uani 1 1 d . . . H19 H -0.1406 0.0675 0.2972 0.036 Uiso 1 1 calc R . . C20 C -0.3058(3) 0.06031(12) 0.3930(3) 0.0285(7) Uani 1 1 d . . . C21 C -0.4472(3) 0.05358(13) 0.3718(3) 0.0345(8) Uani 1 1 d . . . H21 H -0.4959 0.0525 0.4434 0.041 Uiso 1 1 calc R . . C22 C -0.5160(3) 0.04853(14) 0.2453(3) 0.0350(8) Uani 1 1 d . . . H22 H -0.6105 0.0432 0.2321 0.042 Uiso 1 1 calc R . . C23 C -0.4453(3) 0.05133(13) 0.1388(3) 0.0288(7) Uani 1 1 d . . . H23 H -0.4925 0.0483 0.0537 0.035 Uiso 1 1 calc R . . N1 N 0.0624(2) 0.08607(11) 0.8329(3) 0.0323(6) Uani 1 1 d . . . N2 N 0.2695(3) 0.11572(14) 0.9306(3) 0.0492(8) Uani 1 1 d . . . N3 N 0.2758(3) 0.09609(11) 0.8052(3) 0.0310(6) Uani 1 1 d . . . N4 N 0.4217(3) 0.15545(11) 0.6915(3) 0.0347(7) Uani 1 1 d . . . N5 N 0.3828(3) 0.16006(11) 0.5586(3) 0.0383(7) Uani 1 1 d . . . N6 N 0.4458(3) 0.24710(12) 0.6464(3) 0.0428(8) Uani 1 1 d . . . N7 N 0.5598(3) 0.30515(14) 1.0286(4) 0.0619(10) Uani 1 1 d . . . N8 N 0.3256(3) 0.33180(11) 0.2861(3) 0.0372(7) Uani 1 1 d . . . O1 O -0.1019(3) 0.06800(12) 0.5462(3) 0.0620(8) Uani 1 1 d . . . O2 O -0.2967(3) 0.06541(10) 0.6258(2) 0.0481(7) Uani 1 1 d . . . O3 O -0.0985(2) 0.06637(12) 0.0610(2) 0.0551(7) Uani 1 1 d . . . O4 O -0.2918(2) 0.06760(9) -0.0733(2) 0.0369(5) Uani 1 1 d . . . O1W O -0.1242(2) -0.01621(9) 0.7963(2) 0.0387(6) Uani 1 1 d . . . H1A H -0.1485 -0.0335 0.7253 0.058 Uiso 1 1 d R . . H1B H -0.0522 -0.0273 0.8442 0.058 Uiso 1 1 d R . . O2W O 0.1372(3) 0.07602(11) 0.4308(3) 0.0715(9) Uani 1 1 d . . . H2A H 0.2205 0.0811 0.4635 0.107 Uiso 1 1 d R . . H2B H 0.0881 0.0967 0.4744 0.107 Uiso 1 1 d 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 Zn1 0.0289(2) 0.0396(2) 0.0225(2) -0.00533(18) 0.00399(15) -0.00265(18) C1 0.0345(18) 0.0368(19) 0.0274(19) -0.0029(15) 0.0006(16) -0.0060(15) C2 0.039(2) 0.074(3) 0.026(2) -0.0072(19) 0.0063(16) -0.0188(19) C3 0.0340(18) 0.0272(17) 0.040(2) 0.0045(15) 0.0068(16) 0.0022(15) C4 0.0275(18) 0.032(2) 0.051(3) 0.0062(18) 0.0070(16) 0.0013(15) C5 0.0288(18) 0.0342(19) 0.055(3) 0.0041(18) 0.0077(17) -0.0018(16) C6 0.051(2) 0.039(2) 0.072(3) 0.001(2) 0.004(2) 0.0001(19) C7 0.043(2) 0.060(3) 0.069(3) -0.018(2) 0.010(2) -0.005(2) C8 0.041(2) 0.051(2) 0.056(3) -0.003(2) 0.0027(19) -0.0010(18) C9 0.039(2) 0.0332(19) 0.054(3) -0.0038(19) 0.0031(18) -0.0010(16) C10 0.0302(19) 0.037(2) 0.051(3) 0.0098(19) 0.0119(17) 0.0011(16) C11 0.0322(18) 0.040(2) 0.049(3) 0.0090(18) 0.0152(17) 0.0005(16) C12 0.036(2) 0.041(2) 0.046(2) 0.0049(18) 0.0104(17) -0.0016(16) C13 0.040(2) 0.050(2) 0.041(2) 0.0084(19) 0.0090(18) 0.0025(17) C14 0.056(2) 0.043(2) 0.048(3) -0.001(2) 0.013(2) -0.0054(19) C15 0.051(2) 0.036(2) 0.064(3) 0.004(2) 0.017(2) -0.0039(18) C16 0.065(3) 0.0289(19) 0.022(2) 0.0013(15) -0.0016(18) -0.0037(18) C17 0.038(2) 0.0345(19) 0.0233(19) 0.0068(15) 0.0079(15) 0.0081(16) C18 0.0310(17) 0.0244(16) 0.0188(17) 0.0012(13) 0.0034(13) 0.0020(13) C19 0.0284(17) 0.0310(18) 0.029(2) 0.0031(15) 0.0006(14) -0.0004(14) C20 0.0407(19) 0.0267(17) 0.0178(17) 0.0000(13) 0.0035(14) -0.0019(14) C21 0.046(2) 0.0369(19) 0.023(2) -0.0002(15) 0.0158(16) -0.0033(16) C22 0.0261(17) 0.045(2) 0.035(2) 0.0038(16) 0.0069(15) -0.0034(15) C23 0.0330(18) 0.0339(17) 0.0175(18) -0.0016(14) -0.0036(14) -0.0046(14) N1 0.0293(14) 0.0407(16) 0.0260(16) 0.0008(13) 0.0007(12) -0.0070(12) N2 0.0376(17) 0.077(2) 0.0329(19) -0.0076(17) 0.0041(14) -0.0162(16) N3 0.0321(15) 0.0306(14) 0.0305(17) 0.0034(12) 0.0050(12) -0.0033(12) N4 0.0331(15) 0.0294(15) 0.043(2) 0.0069(14) 0.0093(14) 0.0003(12) N5 0.0392(16) 0.0338(16) 0.044(2) 0.0066(14) 0.0111(14) 0.0003(13) N6 0.0357(17) 0.0363(16) 0.055(2) 0.0115(16) 0.0011(15) -0.0030(13) N7 0.057(2) 0.042(2) 0.086(3) -0.011(2) 0.008(2) -0.0044(17) N8 0.0379(16) 0.0381(16) 0.0360(18) 0.0083(15) 0.0066(14) 0.0031(13) O1 0.0587(18) 0.085(2) 0.0353(17) 0.0053(15) -0.0192(13) -0.0185(15) O2 0.0806(18) 0.0485(15) 0.0137(13) -0.0044(11) 0.0013(12) -0.0019(13) O3 0.0306(14) 0.094(2) 0.0431(17) 0.0210(15) 0.0130(12) 0.0091(13) O4 0.0464(13) 0.0476(14) 0.0176(13) 0.0028(11) 0.0078(10) 0.0112(11) O1W 0.0341(12) 0.0417(13) 0.0384(15) -0.0039(11) -0.0016(11) 0.0025(10) O2W 0.088(2) 0.0650(19) 0.058(2) -0.0281(16) -0.0007(16) 0.0038(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O2 2.042(2) . ? Zn1 O4 2.057(2) 1_556 ? Zn1 O1W 2.082(2) . ? Zn1 N1 2.157(2) . ? Zn1 N8 2.217(3) 4_566 ? C1 N1 1.316(4) . ? C1 N3 1.324(4) . ? C1 H1 0.9300 . ? C2 N2 1.297(4) . ? C2 N1 1.362(4) . ? C2 H2 0.9300 . ? C3 N3 1.450(4) . ? C3 N4 1.457(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N6 1.327(4) . ? C4 N4 1.362(4) . ? C4 C5 1.467(5) . ? C5 C9 1.385(5) . ? C5 C6 1.392(5) . ? C6 N7 1.339(5) . ? C6 H6 0.9300 . ? C7 N7 1.333(5) . ? C7 C8 1.373(5) . ? C7 H7 0.9300 . ? C8 C9 1.376(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N5 1.323(4) . ? C10 N6 1.362(5) . ? C10 C11 1.473(5) . ? C11 C12 1.386(4) . ? C11 C15 1.387(5) . ? C12 N8 1.333(4) . ? C12 H12 0.9300 . ? C13 N8 1.336(4) . ? C13 C14 1.378(5) . ? C13 H13 0.9300 . ? C14 C15 1.371(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O1 1.231(4) . ? C16 O2 1.262(4) . ? C16 C20 1.511(4) . ? C17 O3 1.242(4) . ? C17 O4 1.256(4) . ? C17 C18 1.508(4) . ? C18 C19 1.384(4) . ? C18 C23 1.391(4) . ? C19 C20 1.394(4) . ? C19 H19 0.9300 . ? C20 C21 1.389(4) . ? C21 C22 1.378(4) . ? C21 H21 0.9300 . ? C22 C23 1.375(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N2 N3 1.370(4) . ? N4 N5 1.364(4) . ? N8 Zn1 2.217(3) 4_665 ? O4 Zn1 2.057(2) 1_554 ? O1W H1A 0.8341 . ? O1W H1B 0.8437 . ? O2W H2A 0.8500 . ? O2W H2B 0.8501 . ? 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 O2 Zn1 O4 97.03(10) . 1_556 ? O2 Zn1 O1W 91.13(9) . . ? O4 Zn1 O1W 92.13(8) 1_556 . ? O2 Zn1 N1 135.91(10) . . ? O4 Zn1 N1 127.00(10) 1_556 . ? O1W Zn1 N1 89.65(9) . . ? O2 Zn1 N8 91.04(10) . 4_566 ? O4 Zn1 N8 90.92(9) 1_556 4_566 ? O1W Zn1 N8 176.02(9) . 4_566 ? N1 Zn1 N8 86.47(10) . 4_566 ? N1 C1 N3 110.9(3) . . ? N1 C1 H1 124.5 . . ? N3 C1 H1 124.5 . . ? N2 C2 N1 115.6(3) . . ? N2 C2 H2 122.2 . . ? N1 C2 H2 122.2 . . ? N3 C3 N4 111.5(2) . . ? N3 C3 H3A 109.3 . . ? N4 C3 H3A 109.3 . . ? N3 C3 H3B 109.3 . . ? N4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? N6 C4 N4 109.1(3) . . ? N6 C4 C5 121.5(3) . . ? N4 C4 C5 129.3(3) . . ? C9 C5 C6 116.7(4) . . ? C9 C5 C4 126.0(3) . . ? C6 C5 C4 117.2(3) . . ? N7 C6 C5 124.1(4) . . ? N7 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? N7 C7 C8 122.7(4) . . ? N7 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C7 C8 C9 119.3(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C5 119.7(3) . . ? C8 C9 H9 120.1 . . ? C5 C9 H9 120.1 . . ? N5 C10 N6 114.4(3) . . ? N5 C10 C11 123.5(3) . . ? N6 C10 C11 122.0(3) . . ? C12 C11 C15 118.1(4) . . ? C12 C11 C10 118.6(4) . . ? C15 C11 C10 123.2(3) . . ? N8 C12 C11 123.6(4) . . ? N8 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? N8 C13 C14 123.2(4) . . ? N8 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C11 118.8(4) . . ? C14 C15 H15 120.6 . . ? C11 C15 H15 120.6 . . ? O1 C16 O2 122.8(3) . . ? O1 C16 C20 119.8(3) . . ? O2 C16 C20 117.4(3) . . ? O3 C17 O4 122.1(3) . . ? O3 C17 C18 119.1(3) . . ? O4 C17 C18 118.7(3) . . ? C19 C18 C23 118.8(3) . . ? C19 C18 C17 119.9(3) . . ? C23 C18 C17 121.2(3) . . ? C18 C19 C20 121.0(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 118.8(3) . . ? C21 C20 C16 121.5(3) . . ? C19 C20 C16 119.7(3) . . ? C22 C21 C20 120.5(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C18 120.7(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? C1 N1 C2 102.0(3) . . ? C1 N1 Zn1 127.0(2) . . ? C2 N1 Zn1 130.8(2) . . ? C2 N2 N3 102.0(3) . . ? C1 N3 N2 109.5(3) . . ? C1 N3 C3 129.9(3) . . ? N2 N3 C3 120.5(3) . . ? C4 N4 N5 109.7(3) . . ? C4 N4 C3 133.7(3) . . ? N5 N4 C3 116.2(3) . . ? C10 N5 N4 102.8(3) . . ? C4 N6 C10 103.9(3) . . ? C7 N7 C6 117.5(4) . . ? C12 N8 C13 117.2(3) . . ? C12 N8 Zn1 118.0(2) . 4_665 ? C13 N8 Zn1 124.7(2) . 4_665 ? C16 O2 Zn1 105.3(2) . . ? C17 O4 Zn1 108.96(19) . 1_554 ? Zn1 O1W H1A 115.5 . . ? Zn1 O1W H1B 115.2 . . ? H1A O1W H1B 118.4 . . ? H2A O2W H2B 107.7 . . ? 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 N6 C4 C5 C9 -164.0(3) . . . . ? N4 C4 C5 C9 16.3(5) . . . . ? N6 C4 C5 C6 11.8(5) . . . . ? N4 C4 C5 C6 -168.0(3) . . . . ? C9 C5 C6 N7 0.4(5) . . . . ? C4 C5 C6 N7 -175.8(3) . . . . ? N7 C7 C8 C9 -0.4(6) . . . . ? C7 C8 C9 C5 -0.3(5) . . . . ? C6 C5 C9 C8 0.3(5) . . . . ? C4 C5 C9 C8 176.1(3) . . . . ? N5 C10 C11 C12 169.1(3) . . . . ? N6 C10 C11 C12 -7.0(5) . . . . ? N5 C10 C11 C15 -6.9(5) . . . . ? N6 C10 C11 C15 177.1(3) . . . . ? C15 C11 C12 N8 -0.1(5) . . . . ? C10 C11 C12 N8 -176.3(3) . . . . ? N8 C13 C14 C15 0.6(5) . . . . ? C13 C14 C15 C11 0.1(5) . . . . ? C12 C11 C15 C14 -0.3(5) . . . . ? C10 C11 C15 C14 175.6(3) . . . . ? O3 C17 C18 C19 6.8(4) . . . . ? O4 C17 C18 C19 -170.7(3) . . . . ? O3 C17 C18 C23 -175.0(3) . . . . ? O4 C17 C18 C23 7.5(4) . . . . ? C23 C18 C19 C20 -0.6(4) . . . . ? C17 C18 C19 C20 177.7(3) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? C18 C19 C20 C16 179.8(3) . . . . ? O1 C16 C20 C21 176.6(3) . . . . ? O2 C16 C20 C21 -3.9(4) . . . . ? O1 C16 C20 C19 -3.3(5) . . . . ? O2 C16 C20 C19 176.2(3) . . . . ? C19 C20 C21 C22 1.1(4) . . . . ? C16 C20 C21 C22 -178.8(3) . . . . ? C20 C21 C22 C23 -1.3(5) . . . . ? C21 C22 C23 C18 0.6(5) . . . . ? C19 C18 C23 C22 0.4(4) . . . . ? C17 C18 C23 C22 -177.9(3) . . . . ? N3 C1 N1 C2 0.0(4) . . . . ? N3 C1 N1 Zn1 174.55(19) . . . . ? N2 C2 N1 C1 0.9(4) . . . . ? N2 C2 N1 Zn1 -173.4(2) . . . . ? O2 Zn1 N1 C1 -16.5(3) . . . . ? O4 Zn1 N1 C1 167.2(2) 1_556 . . . ? O1W Zn1 N1 C1 74.8(3) . . . . ? N8 Zn1 N1 C1 -104.3(3) 4_566 . . . ? O2 Zn1 N1 C2 156.5(3) . . . . ? O4 Zn1 N1 C2 -19.8(3) 1_556 . . . ? O1W Zn1 N1 C2 -112.2(3) . . . . ? N8 Zn1 N1 C2 68.7(3) 4_566 . . . ? N1 C2 N2 N3 -1.3(4) . . . . ? N1 C1 N3 N2 -0.8(4) . . . . ? N1 C1 N3 C3 -176.7(3) . . . . ? C2 N2 N3 C1 1.2(4) . . . . ? C2 N2 N3 C3 177.6(3) . . . . ? N4 C3 N3 C1 91.2(4) . . . . ? N4 C3 N3 N2 -84.4(4) . . . . ? N6 C4 N4 N5 -0.6(3) . . . . ? C5 C4 N4 N5 179.1(3) . . . . ? N6 C4 N4 C3 -173.3(3) . . . . ? C5 C4 N4 C3 6.4(6) . . . . ? N3 C3 N4 C4 75.8(4) . . . . ? N3 C3 N4 N5 -96.6(3) . . . . ? N6 C10 N5 N4 -0.5(3) . . . . ? C11 C10 N5 N4 -176.8(3) . . . . ? C4 N4 N5 C10 0.7(3) . . . . ? C3 N4 N5 C10 174.8(3) . . . . ? N4 C4 N6 C10 0.3(4) . . . . ? C5 C4 N6 C10 -179.5(3) . . . . ? N5 C10 N6 C4 0.1(4) . . . . ? C11 C10 N6 C4 176.5(3) . . . . ? C8 C7 N7 C6 0.9(6) . . . . ? C5 C6 N7 C7 -1.0(6) . . . . ? C11 C12 N8 C13 0.8(5) . . . . ? C11 C12 N8 Zn1 -176.4(2) . . . 4_665 ? C14 C13 N8 C12 -1.0(5) . . . . ? C14 C13 N8 Zn1 176.0(2) . . . 4_665 ? O1 C16 O2 Zn1 0.2(4) . . . . ? C20 C16 O2 Zn1 -179.3(2) . . . . ? O4 Zn1 O2 C16 -176.7(2) 1_556 . . . ? O1W Zn1 O2 C16 -84.4(2) . . . . ? N1 Zn1 O2 C16 6.3(3) . . . . ? N8 Zn1 O2 C16 92.3(2) 4_566 . . . ? O3 C17 O4 Zn1 3.5(4) . . . 1_554 ? C18 C17 O4 Zn1 -179.1(2) . . . 1_554 ? 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 O1W H1A O2W 0.83 1.89 2.691(3) 160.0 3_556 O1W H1B O3 0.84 1.89 2.720(3) 169.0 3_556 O2W H2A N5 0.85 2.53 3.235(4) 140.8 . O2W H2B O1 0.85 2.21 2.785(4) 125.2 . O2W H2B N7 0.85 2.36 3.060(4) 139.4 4_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.419 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.062 #========================================================== data_compound-8 _database_code_depnum_ccdc_archive 'CCDC 892072' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H18 N8 O8 Zn2' _chemical_formula_sum 'C24 H18 N8 O8 Zn2' _chemical_formula_weight 677.20 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 'C 2/c' _symmetry_space_group_name_hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.5723(13) _cell_length_b 10.2646(3) _cell_length_c 20.2916(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.618(6) _cell_angle_gamma 90.00 _cell_volume 4916.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 3.0422 _cell_measurement_theta_max 29.1643 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 2.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6426 _exptl_absorpt_correction_T_max 0.6879 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8998 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4493 _reflns_number_gt 3274 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0268P)^2^+0.0000P] 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_number_reflns 4493 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _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 Zn1 Zn 0.59280(2) 0.11926(4) 0.16217(3) 0.02020(14) Uani 1 1 d . . . Zn2 Zn 0.58624(3) -0.33245(4) 0.53547(3) 0.03054(17) Uani 1 1 d . . . C1 C 0.4763(2) -0.0160(4) 0.0848(3) 0.0344(12) Uani 1 1 d . . . H1 H 0.4945 -0.0871 0.0748 0.041 Uiso 1 1 calc R . . C2 C 0.4641(2) 0.1654(4) 0.1232(2) 0.0294(11) Uani 1 1 d . . . H2 H 0.4694 0.2468 0.1449 0.035 Uiso 1 1 calc R . . C3 C 0.35928(19) 0.1541(4) 0.0846(2) 0.0284(11) Uani 1 1 d . . . H3A H 0.3476 0.1023 0.1165 0.034 Uiso 1 1 calc R . . H3B H 0.3619 0.2442 0.0999 0.034 Uiso 1 1 calc R . . C4 C 0.27123(19) 0.2073(4) -0.0910(2) 0.0216(10) Uani 1 1 d . . . C5 C 0.25345(18) 0.2862(4) -0.1570(2) 0.0211(9) Uani 1 1 d . . . C6 C 0.29143(19) 0.3756(4) -0.1662(2) 0.0322(11) Uani 1 1 d . . . H6 H 0.3285 0.3818 -0.1330 0.039 Uiso 1 1 calc R . . C7 C 0.2723(2) 0.4539(4) -0.2255(3) 0.0377(12) Uani 1 1 d . . . H7 H 0.2965 0.5140 -0.2334 0.045 Uiso 1 1 calc R . . C8 C 0.2176(2) 0.4432(4) -0.2729(2) 0.0283(11) Uani 1 1 d . . . H8 H 0.2054 0.4976 -0.3126 0.034 Uiso 1 1 calc R . . C9 C 0.19968(19) 0.2803(4) -0.2076(2) 0.0204(9) Uani 1 1 d . . . H9 H 0.1750 0.2188 -0.2019 0.024 Uiso 1 1 calc R . . C10 C 0.26950(19) 0.0715(4) -0.0142(2) 0.0240(10) Uani 1 1 d . . . C11 C 0.25318(19) -0.0326(4) 0.0250(2) 0.0275(10) Uani 1 1 d . . . C12 C 0.2920(2) -0.1198(4) 0.0694(3) 0.0393(12) Uani 1 1 d . . . H12 H 0.3300 -0.1159 0.0757 0.047 Uiso 1 1 calc R . . C13 C 0.2731(2) -0.2124(5) 0.1040(3) 0.0479(14) Uani 1 1 d . . . H13 H 0.2980 -0.2727 0.1342 0.057 Uiso 1 1 calc R . . C14 C 0.2167(2) -0.2140(5) 0.0931(3) 0.0438(13) Uani 1 1 d . . . H14 H 0.2045 -0.2766 0.1171 0.053 Uiso 1 1 calc R . . C15 C 0.19714(19) -0.0422(4) 0.0168(2) 0.0261(10) Uani 1 1 d . . . H15 H 0.1714 0.0165 -0.0136 0.031 Uiso 1 1 calc R . . C16 C 0.59299(18) -0.0994(4) 0.2293(2) 0.0243(10) Uani 1 1 d . . . C17 C 0.58185(17) -0.5756(4) 0.1678(2) 0.0198(9) Uani 1 1 d . . . C18 C 0.56425(18) -0.4307(4) 0.3942(2) 0.0242(10) Uani 1 1 d . . . C19 C 0.57041(17) -0.3987(3) 0.3250(2) 0.0170(9) Uani 1 1 d . . . C20 C 0.57581(17) -0.2695(3) 0.3076(2) 0.0182(9) Uani 1 1 d . . . H20 H 0.5738 -0.2031 0.3377 0.022 Uiso 1 1 calc R . . C21 C 0.58422(17) -0.2390(3) 0.2459(2) 0.0179(9) Uani 1 1 d . . . C22 C 0.58507(18) -0.3379(3) 0.2002(2) 0.0203(9) Uani 1 1 d . . . H22 H 0.5896 -0.3175 0.1580 0.024 Uiso 1 1 calc R . . C23 C 0.57928(17) -0.4679(3) 0.2162(2) 0.0171(9) Uani 1 1 d . . . C24 C 0.57234(18) -0.4958(3) 0.2793(2) 0.0197(10) Uani 1 1 d . . . H24 H 0.5689 -0.5822 0.2908 0.024 Uiso 1 1 calc R . . N1 N 0.50484(15) 0.0892(3) 0.12220(19) 0.0258(9) Uani 1 1 d . . . N2 N 0.42130(17) -0.0093(3) 0.0642(2) 0.0363(10) Uani 1 1 d . . . N3 N 0.41429(15) 0.1102(3) 0.08892(18) 0.0243(8) Uani 1 1 d . . . N4 N 0.31742(15) 0.1431(3) 0.01292(18) 0.0226(8) Uani 1 1 d . . . N5 N 0.31855(15) 0.2312(3) -0.03674(19) 0.0260(8) Uani 1 1 d . . . N6 N 0.23893(15) 0.1098(3) -0.08018(19) 0.0273(9) Uani 1 1 d . . . N7 N 0.18032(15) 0.3582(3) -0.26522(18) 0.0216(8) Uani 1 1 d . . . N8 N 0.17793(16) -0.1309(3) 0.0498(2) 0.0303(9) Uani 1 1 d . . . O1 O 0.60103(12) -0.0798(2) 0.17216(15) 0.0266(7) Uani 1 1 d . . . O2 O 0.59228(15) -0.0108(3) 0.27057(17) 0.0380(9) Uani 1 1 d . . . O3 O 0.58800(14) -0.5438(3) 0.11094(16) 0.0336(8) Uani 1 1 d . . . O4 O 0.57873(13) -0.6896(2) 0.18765(15) 0.0269(7) Uani 1 1 d . . . O5 O 0.56515(14) -0.3334(3) 0.43289(15) 0.0348(8) Uani 1 1 d . . . O6 O 0.56057(15) -0.5458(3) 0.40966(16) 0.0406(9) Uani 1 1 d . . . O7 O 0.60326(13) -0.1603(2) 0.57399(15) 0.0261(7) Uani 1 1 d . . . H7' H 0.5998 -0.1095 0.5420 0.039 Uiso 1 1 d R . . O1W O 0.49015(15) -0.3406(3) 0.50325(18) 0.0507(10) Uani 1 1 d . . . H1A H 0.4631 -0.2994 0.4719 0.076 Uiso 1 1 d R . . H1B H 0.4776 -0.3736 0.5327 0.076 Uiso 1 1 d 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 Zn1 0.0245(3) 0.0148(2) 0.0213(3) 0.0011(2) 0.0087(2) -0.0017(2) Zn2 0.0550(4) 0.0212(3) 0.0202(3) 0.0005(2) 0.0198(3) 0.0012(2) C1 0.029(3) 0.027(2) 0.045(3) -0.013(2) 0.011(3) 0.000(2) C2 0.029(3) 0.021(2) 0.034(3) -0.003(2) 0.008(3) -0.001(2) C3 0.028(3) 0.031(2) 0.027(3) 0.000(2) 0.012(2) 0.003(2) C4 0.021(3) 0.021(2) 0.024(2) 0.0031(19) 0.009(2) 0.0020(19) C5 0.019(3) 0.022(2) 0.021(2) -0.0018(19) 0.006(2) 0.0027(18) C6 0.019(3) 0.041(3) 0.032(3) 0.008(2) 0.005(2) -0.004(2) C7 0.032(3) 0.041(3) 0.040(3) 0.014(2) 0.014(3) -0.009(2) C8 0.030(3) 0.028(2) 0.025(3) 0.008(2) 0.009(2) 0.000(2) C9 0.025(3) 0.017(2) 0.022(2) 0.0002(19) 0.012(2) -0.0019(18) C10 0.021(3) 0.025(2) 0.025(3) 0.004(2) 0.007(2) 0.002(2) C11 0.027(3) 0.027(2) 0.027(3) 0.005(2) 0.008(2) -0.002(2) C12 0.023(3) 0.043(3) 0.045(3) 0.017(3) 0.006(3) -0.004(2) C13 0.034(3) 0.045(3) 0.052(4) 0.029(3) 0.002(3) 0.003(2) C14 0.040(4) 0.050(3) 0.038(3) 0.014(3) 0.012(3) -0.013(3) C15 0.028(3) 0.023(2) 0.024(2) 0.004(2) 0.007(2) -0.001(2) C16 0.023(3) 0.018(2) 0.027(2) 0.002(2) 0.004(2) -0.0011(18) C17 0.014(2) 0.021(2) 0.023(2) -0.0069(19) 0.006(2) -0.0058(17) C18 0.026(3) 0.030(2) 0.016(2) -0.003(2) 0.008(2) 0.000(2) C19 0.018(2) 0.017(2) 0.015(2) 0.0026(18) 0.005(2) -0.0020(17) C20 0.021(3) 0.016(2) 0.018(2) -0.0082(18) 0.008(2) 0.0010(17) C21 0.020(3) 0.0135(19) 0.017(2) 0.0010(17) 0.004(2) -0.0003(17) C22 0.025(3) 0.022(2) 0.017(2) -0.0008(18) 0.012(2) -0.0025(18) C23 0.022(3) 0.0110(18) 0.021(2) -0.0009(17) 0.012(2) 0.0000(17) C24 0.026(3) 0.012(2) 0.022(2) 0.0020(18) 0.010(2) -0.0014(17) N1 0.025(2) 0.0175(18) 0.033(2) 0.0000(17) 0.010(2) -0.0017(16) N2 0.031(3) 0.028(2) 0.044(3) -0.0139(19) 0.009(2) -0.0010(18) N3 0.025(2) 0.0211(18) 0.023(2) 0.0027(16) 0.0055(19) -0.0002(17) N4 0.016(2) 0.0278(19) 0.0199(19) 0.0040(16) 0.0027(18) -0.0009(16) N5 0.022(2) 0.030(2) 0.024(2) 0.0061(17) 0.006(2) -0.0032(17) N6 0.022(2) 0.0271(19) 0.028(2) 0.0039(17) 0.0041(19) -0.0044(17) N7 0.024(2) 0.0202(18) 0.0200(19) 0.0001(15) 0.0072(18) 0.0000(15) N8 0.034(3) 0.031(2) 0.029(2) 0.0037(18) 0.015(2) -0.0025(18) O1 0.033(2) 0.0193(14) 0.0269(17) 0.0066(13) 0.0103(16) -0.0016(13) O2 0.059(3) 0.0165(15) 0.044(2) -0.0055(15) 0.026(2) -0.0042(15) O3 0.055(2) 0.0271(16) 0.0306(18) -0.0093(14) 0.0297(19) -0.0098(15) O4 0.040(2) 0.0122(14) 0.0301(18) -0.0055(13) 0.0151(17) 0.0023(13) O5 0.056(2) 0.0326(17) 0.0185(17) -0.0021(14) 0.0167(18) 0.0023(15) O6 0.071(3) 0.0263(17) 0.035(2) 0.0041(15) 0.033(2) -0.0058(16) O7 0.045(2) 0.0178(14) 0.0212(16) 0.0004(12) 0.0190(17) 0.0016(13) O1W 0.048(3) 0.067(2) 0.039(2) 0.0050(18) 0.019(2) -0.0086(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Zn1 O7 1.954(2) 6 ? Zn1 O1 2.056(3) . ? Zn1 O4 2.095(2) 1_565 ? Zn1 N1 2.100(4) . ? Zn1 N7 2.167(4) 8_556 ? Zn2 O7 1.913(2) . ? Zn2 O5 1.939(3) . ? Zn2 O3 1.977(3) 6_546 ? Zn2 N8 2.280(4) 8_546 ? Zn2 O1W 2.288(3) . ? C1 N2 1.305(6) . ? C1 N1 1.360(5) . ? C1 H1 0.9300 . ? C2 N1 1.309(5) . ? C2 N3 1.321(5) . ? C2 H2 0.9300 . ? C3 N4 1.441(6) . ? C3 N3 1.447(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N5 1.309(5) . ? C4 N6 1.368(5) . ? C4 C5 1.478(5) . ? C5 C9 1.365(6) . ? C5 C6 1.400(5) . ? C6 C7 1.372(6) . ? C6 H6 0.9300 . ? C7 C8 1.363(6) . ? C7 H7 0.9300 . ? C8 N7 1.346(5) . ? C8 H8 0.9300 . ? C9 N7 1.345(5) . ? C9 H9 0.9300 . ? C10 N6 1.324(5) . ? C10 N4 1.351(5) . ? C10 C11 1.484(5) . ? C11 C15 1.381(6) . ? C11 C12 1.383(6) . ? C12 C13 1.376(6) . ? C12 H12 0.9300 . ? C13 C14 1.372(7) . ? C13 H13 0.9300 . ? C14 N8 1.346(6) . ? C14 H14 0.9300 . ? C15 N8 1.332(5) . ? C15 H15 0.9300 . ? C16 O2 1.242(5) . ? C16 O1 1.268(5) . ? C16 C21 1.509(5) . ? C17 O4 1.249(4) . ? C17 O3 1.266(4) . ? C17 C23 1.497(5) . ? C18 O6 1.235(5) . ? C18 O5 1.265(5) . ? C18 C19 1.508(5) . ? C19 C24 1.375(5) . ? C19 C20 1.393(5) . ? C20 C21 1.385(5) . ? C20 H20 0.9300 . ? C21 C22 1.381(5) . ? C22 C23 1.395(5) . ? C22 H22 0.9300 . ? C23 C24 1.387(5) . ? C24 H24 0.9300 . ? N2 N3 1.362(4) . ? N4 N5 1.362(4) . ? N7 Zn1 2.167(4) 8_455 ? N8 Zn2 2.280(4) 8_445 ? O3 Zn2 1.977(3) 6_545 ? O4 Zn1 2.095(2) 1_545 ? O7 Zn1 1.954(2) 6_556 ? O7 H7' 0.8106 . ? O1W H1A 0.8500 . ? O1W H1B 0.8497 . ? 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 O7 Zn1 O1 105.06(10) 6 . ? O7 Zn1 O4 96.94(10) 6 1_565 ? O1 Zn1 O4 157.98(10) . 1_565 ? O7 Zn1 N1 100.45(13) 6 . ? O1 Zn1 N1 86.91(12) . . ? O4 Zn1 N1 88.43(12) 1_565 . ? O7 Zn1 N7 97.49(12) 6 8_556 ? O1 Zn1 N7 89.96(12) . 8_556 ? O4 Zn1 N7 87.86(12) 1_565 8_556 ? N1 Zn1 N7 161.99(12) . 8_556 ? O7 Zn2 O5 111.63(12) . . ? O7 Zn2 O3 110.07(11) . 6_546 ? O5 Zn2 O3 137.94(12) . 6_546 ? O7 Zn2 N8 92.23(12) . 8_546 ? O5 Zn2 N8 89.10(13) . 8_546 ? O3 Zn2 N8 94.53(12) 6_546 8_546 ? O7 Zn2 O1W 101.59(12) . . ? O5 Zn2 O1W 82.43(12) . . ? O3 Zn2 O1W 84.26(13) 6_546 . ? N8 Zn2 O1W 165.70(12) 8_546 . ? N2 C1 N1 114.7(4) . . ? N2 C1 H1 122.6 . . ? N1 C1 H1 122.6 . . ? N1 C2 N3 110.3(4) . . ? N1 C2 H2 124.8 . . ? N3 C2 H2 124.8 . . ? N4 C3 N3 111.4(3) . . ? N4 C3 H3A 109.4 . . ? N3 C3 H3A 109.4 . . ? N4 C3 H3B 109.4 . . ? N3 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N5 C4 N6 115.0(4) . . ? N5 C4 C5 121.5(3) . . ? N6 C4 C5 123.5(4) . . ? C9 C5 C6 118.6(4) . . ? C9 C5 C4 121.8(3) . . ? C6 C5 C4 119.5(4) . . ? C7 C6 C5 118.0(4) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? N7 C8 C7 123.5(4) . . ? N7 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? N7 C9 C5 123.8(4) . . ? N7 C9 H9 118.1 . . ? C5 C9 H9 118.1 . . ? N6 C10 N4 109.9(3) . . ? N6 C10 C11 125.2(4) . . ? N4 C10 C11 124.8(4) . . ? C15 C11 C12 119.0(4) . . ? C15 C11 C10 118.6(4) . . ? C12 C11 C10 122.4(4) . . ? C13 C12 C11 118.3(4) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C14 C13 C12 118.7(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? N8 C14 C13 124.2(4) . . ? N8 C14 H14 117.9 . . ? C13 C14 H14 117.9 . . ? N8 C15 C11 123.7(4) . . ? N8 C15 H15 118.2 . . ? C11 C15 H15 118.2 . . ? O2 C16 O1 123.4(3) . . ? O2 C16 C21 120.2(3) . . ? O1 C16 C21 116.4(3) . . ? O4 C17 O3 125.5(3) . . ? O4 C17 C23 117.1(3) . . ? O3 C17 C23 117.3(3) . . ? O6 C18 O5 125.6(4) . . ? O6 C18 C19 119.4(3) . . ? O5 C18 C19 115.0(3) . . ? C24 C19 C20 119.1(3) . . ? C24 C19 C18 121.0(3) . . ? C20 C19 C18 119.9(3) . . ? C21 C20 C19 120.6(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.3(3) . . ? C22 C21 C16 120.4(3) . . ? C20 C21 C16 120.4(3) . . ? C21 C22 C23 121.1(3) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 118.4(3) . . ? C24 C23 C17 120.4(3) . . ? C22 C23 C17 121.2(3) . . ? C19 C24 C23 121.5(3) . . ? C19 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C2 N1 C1 102.9(4) . . ? C2 N1 Zn1 130.3(3) . . ? C1 N1 Zn1 126.7(3) . . ? C1 N2 N3 102.0(3) . . ? C2 N3 N2 110.1(3) . . ? C2 N3 C3 128.1(4) . . ? N2 N3 C3 121.3(3) . . ? C10 N4 N5 109.5(3) . . ? C10 N4 C3 131.2(3) . . ? N5 N4 C3 118.4(3) . . ? C4 N5 N4 102.8(3) . . ? C10 N6 C4 102.8(4) . . ? C9 N7 C8 116.5(4) . . ? C9 N7 Zn1 126.4(3) . 8_455 ? C8 N7 Zn1 116.4(3) . 8_455 ? C15 N8 C14 116.1(4) . . ? C15 N8 Zn2 127.5(3) . 8_445 ? C14 N8 Zn2 116.3(3) . 8_445 ? C16 O1 Zn1 101.6(2) . . ? C17 O3 Zn2 124.5(2) . 6_545 ? C17 O4 Zn1 139.4(2) . 1_545 ? C18 O5 Zn2 127.0(3) . . ? Zn2 O7 Zn1 118.92(12) . 6_556 ? Zn2 O7 H7' 109.3 . . ? Zn1 O7 H7' 125.6 6_556 . ? Zn2 O1W H1A 132.2 . . ? Zn2 O1W H1B 117.9 . . ? H1A O1W H1B 107.7 . . ? 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 N5 C4 C5 C9 -166.4(4) . . . . ? N6 C4 C5 C9 10.1(6) . . . . ? N5 C4 C5 C6 9.5(5) . . . . ? N6 C4 C5 C6 -174.1(4) . . . . ? C9 C5 C6 C7 0.6(6) . . . . ? C4 C5 C6 C7 -175.4(4) . . . . ? C5 C6 C7 C8 0.5(6) . . . . ? C6 C7 C8 N7 -0.4(7) . . . . ? C6 C5 C9 N7 -1.9(6) . . . . ? C4 C5 C9 N7 174.0(3) . . . . ? N6 C10 C11 C15 -38.7(6) . . . . ? N4 C10 C11 C15 139.9(4) . . . . ? N6 C10 C11 C12 141.4(5) . . . . ? N4 C10 C11 C12 -40.0(6) . . . . ? C15 C11 C12 C13 -0.4(7) . . . . ? C10 C11 C12 C13 179.5(4) . . . . ? C11 C12 C13 C14 -0.1(8) . . . . ? C12 C13 C14 N8 0.6(8) . . . . ? C12 C11 C15 N8 0.6(7) . . . . ? C10 C11 C15 N8 -179.3(4) . . . . ? O6 C18 C19 C24 -0.4(6) . . . . ? O5 C18 C19 C24 177.4(4) . . . . ? O6 C18 C19 C20 -178.6(4) . . . . ? O5 C18 C19 C20 -0.8(6) . . . . ? C24 C19 C20 C21 -1.3(6) . . . . ? C18 C19 C20 C21 176.9(4) . . . . ? C19 C20 C21 C22 2.4(6) . . . . ? C19 C20 C21 C16 -176.9(4) . . . . ? O2 C16 C21 C22 -179.9(4) . . . . ? O1 C16 C21 C22 -0.1(6) . . . . ? O2 C16 C21 C20 -0.6(6) . . . . ? O1 C16 C21 C20 179.2(4) . . . . ? C20 C21 C22 C23 -1.9(6) . . . . ? C16 C21 C22 C23 177.4(4) . . . . ? C21 C22 C23 C24 0.3(6) . . . . ? C21 C22 C23 C17 -178.2(4) . . . . ? O4 C17 C23 C24 -1.5(6) . . . . ? O3 C17 C23 C24 179.7(4) . . . . ? O4 C17 C23 C22 177.0(4) . . . . ? O3 C17 C23 C22 -1.8(6) . . . . ? C20 C19 C24 C23 -0.3(6) . . . . ? C18 C19 C24 C23 -178.5(4) . . . . ? C22 C23 C24 C19 0.8(6) . . . . ? C17 C23 C24 C19 179.3(4) . . . . ? N3 C2 N1 C1 0.1(5) . . . . ? N3 C2 N1 Zn1 177.1(3) . . . . ? N2 C1 N1 C2 -1.0(5) . . . . ? N2 C1 N1 Zn1 -178.2(3) . . . . ? O7 Zn1 N1 C2 -102.1(4) 6 . . . ? O1 Zn1 N1 C2 153.1(4) . . . . ? O4 Zn1 N1 C2 -5.4(4) 1_565 . . . ? N7 Zn1 N1 C2 72.8(6) 8_556 . . . ? O7 Zn1 N1 C1 74.2(4) 6 . . . ? O1 Zn1 N1 C1 -30.5(4) . . . . ? O4 Zn1 N1 C1 171.0(4) 1_565 . . . ? N7 Zn1 N1 C1 -110.8(5) 8_556 . . . ? N1 C1 N2 N3 1.4(5) . . . . ? N1 C2 N3 N2 0.7(5) . . . . ? N1 C2 N3 C3 172.2(4) . . . . ? C1 N2 N3 C2 -1.3(5) . . . . ? C1 N2 N3 C3 -173.4(4) . . . . ? N4 C3 N3 C2 136.5(4) . . . . ? N4 C3 N3 N2 -53.0(5) . . . . ? N6 C10 N4 N5 -0.1(4) . . . . ? C11 C10 N4 N5 -178.9(3) . . . . ? N6 C10 N4 C3 168.7(4) . . . . ? C11 C10 N4 C3 -10.1(6) . . . . ? N3 C3 N4 C10 117.5(4) . . . . ? N3 C3 N4 N5 -74.5(4) . . . . ? N6 C4 N5 N4 0.3(4) . . . . ? C5 C4 N5 N4 177.0(3) . . . . ? C10 N4 N5 C4 -0.1(4) . . . . ? C3 N4 N5 C4 -170.6(3) . . . . ? N4 C10 N6 C4 0.3(4) . . . . ? C11 C10 N6 C4 179.0(4) . . . . ? N5 C4 N6 C10 -0.4(4) . . . . ? C5 C4 N6 C10 -177.0(3) . . . . ? C5 C9 N7 C8 1.9(5) . . . . ? C5 C9 N7 Zn1 -168.3(3) . . . 8_455 ? C7 C8 N7 C9 -0.7(6) . . . . ? C7 C8 N7 Zn1 170.5(3) . . . 8_455 ? C11 C15 N8 C14 -0.2(6) . . . . ? C11 C15 N8 Zn2 -175.3(3) . . . 8_445 ? C13 C14 N8 C15 -0.4(7) . . . . ? C13 C14 N8 Zn2 175.3(4) . . . 8_445 ? O2 C16 O1 Zn1 -12.2(5) . . . . ? C21 C16 O1 Zn1 168.0(3) . . . . ? O7 Zn1 O1 C16 -179.1(3) 6 . . . ? O4 Zn1 O1 C16 -1.0(5) 1_565 . . . ? N1 Zn1 O1 C16 -79.1(3) . . . . ? N7 Zn1 O1 C16 83.2(3) 8_556 . . . ? O4 C17 O3 Zn2 6.6(6) . . . 6_545 ? C23 C17 O3 Zn2 -174.8(3) . . . 6_545 ? O3 C17 O4 Zn1 12.5(7) . . . 1_545 ? C23 C17 O4 Zn1 -166.1(3) . . . 1_545 ? O6 C18 O5 Zn2 22.3(6) . . . . ? C19 C18 O5 Zn2 -155.5(3) . . . . ? O7 Zn2 O5 C18 162.4(3) . . . . ? O3 Zn2 O5 C18 -25.5(4) 6_546 . . . ? N8 Zn2 O5 C18 70.3(3) 8_546 . . . ? O1W Zn2 O5 C18 -98.1(3) . . . . ? O5 Zn2 O7 Zn1 153.18(16) . . . 6_556 ? O3 Zn2 O7 Zn1 -21.3(2) 6_546 . . 6_556 ? N8 Zn2 O7 Zn1 -116.90(17) 8_546 . . 6_556 ? O1W Zn2 O7 Zn1 66.81(18) . . . 6_556 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.551 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.088 #==========================================================end