# 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 #TrackingRef 'w6663.cif' _publ_contact_author ; J. H. Qin ; _publ_contact_author_address ; College of Chemistry and Chemical Engineering Luoyang Normal University Luoyang 471022 P. R. China ; _publ_contact_author_phone '086 379 65526003' _publ_contact_author_fax '086 379 65526003' _publ_contact_author_email 'jh q128105@126.com' _publ_contact_author_name 'J. H. Qin' loop_ _publ_author_name J.H.Qin 'Lufang Ma' 'Hu Yue' 'Liya Wang' data_w6663 _database_code_depnum_ccdc_archive 'CCDC 849773' #TrackingRef 'w6663.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N2 O5 Zn' _chemical_formula_weight 404.69 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 C2/c 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 24.189(3) _cell_length_b 9.4989(10) _cell_length_c 17.9964(19) _cell_angle_alpha 90.00 _cell_angle_beta 126.0110(10) _cell_angle_gamma 90.00 _cell_volume 3344.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3747 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 25.83 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 1.502 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7034 _exptl_absorpt_correction_T_max 0.8868 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12141 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3119 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+2.9585P] 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 3119 _refine_ls_number_parameters 236 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.040 _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 0.061688(12) 0.29644(3) 0.380761(16) 0.02451(9) Uani 1 1 d . . . O1 O 0.08893(8) 0.38157(19) 0.49385(11) 0.0406(4) Uani 1 1 d . . . O2 O 0.19855(9) 0.3507(2) 0.55099(12) 0.0511(5) Uani 1 1 d . . . O3 O 0.03811(8) 0.68394(17) 0.67912(11) 0.0351(4) Uani 1 1 d . . . O4 O 0.09517(8) 0.59789(17) 0.82186(11) 0.0348(4) Uani 1 1 d . . . O5 O 0.31779(8) 0.4556(2) 0.89263(11) 0.0468(5) Uani 1 1 d . . . N1 N 0.08592(9) 0.09883(19) 0.37734(13) 0.0297(4) Uani 1 1 d . . . N2 N 0.14216(10) -0.0859(2) 0.37786(14) 0.0342(5) Uani 1 1 d . . . C1 C 0.15334(12) 0.3870(2) 0.55821(16) 0.0324(5) Uani 1 1 d . . . C2 C 0.17071(11) 0.4428(2) 0.64817(15) 0.0286(5) Uani 1 1 d . . . C3 C 0.23666(11) 0.4228(2) 0.72743(16) 0.0326(5) Uani 1 1 d . . . H3 H 0.2690 0.3770 0.7239 0.039 Uiso 1 1 calc R . . C4 C 0.25431(11) 0.4706(2) 0.81132(15) 0.0318(5) Uani 1 1 d . . . C5 C 0.20571(11) 0.5366(2) 0.81719(15) 0.0300(5) Uani 1 1 d . . . H5 H 0.2173 0.5678 0.8737 0.036 Uiso 1 1 calc R . . C6 C 0.14000(10) 0.5557(2) 0.73849(14) 0.0244(5) Uani 1 1 d . . . C7 C 0.12231(11) 0.5103(2) 0.65359(15) 0.0279(5) Uani 1 1 d . . . H7 H 0.0783 0.5251 0.6008 0.033 Uiso 1 1 calc R . . C8 C 0.08693(11) 0.6182(2) 0.74675(15) 0.0259(5) Uani 1 1 d . . . C9 C 0.36541(15) 0.3750(4) 0.8901(2) 0.0747(11) Uani 1 1 d . . . H9A H 0.3479 0.2815 0.8694 0.112 Uiso 1 1 calc R . . H9B H 0.4076 0.3706 0.9506 0.112 Uiso 1 1 calc R . . H9C H 0.3732 0.4177 0.8487 0.112 Uiso 1 1 calc R . . C10 C 0.05225(11) -0.0225(2) 0.37308(15) 0.0296(5) Uani 1 1 d . . . C11 C 0.08715(12) -0.1391(2) 0.37356(16) 0.0334(5) Uani 1 1 d . . . C12 C 0.06625(14) -0.2761(3) 0.37269(19) 0.0486(7) Uani 1 1 d . . . H12 H 0.0895 -0.3540 0.3726 0.058 Uiso 1 1 calc R . . C13 C 0.00963(15) -0.2899(3) 0.3719(2) 0.0572(8) Uani 1 1 d . . . H13 H -0.0054 -0.3797 0.3726 0.069 Uiso 1 1 calc R . . C14 C -0.02637(14) -0.1738(3) 0.3702(2) 0.0543(8) Uani 1 1 d . . . H14 H -0.0649 -0.1882 0.3689 0.065 Uiso 1 1 calc R . . C15 C -0.00598(12) -0.0382(3) 0.37029(18) 0.0409(6) Uani 1 1 d . . . H15 H -0.0302 0.0393 0.3686 0.049 Uiso 1 1 calc R . . C16 C 0.13930(12) 0.0544(2) 0.38074(16) 0.0328(5) Uani 1 1 d . . . H16 H 0.1713 0.1144 0.3847 0.039 Uiso 1 1 calc R . . C17 C 0.19385(13) -0.1668(3) 0.37753(18) 0.0449(7) Uani 1 1 d DU . . H17A H 0.2077 -0.1132 0.3452 0.054 Uiso 1 1 calc R . . H17B H 0.1734 -0.2539 0.3441 0.054 Uiso 1 1 calc R . . C18 C 0.25636(13) -0.2013(3) 0.47253(19) 0.0464(7) Uani 1 1 d DU . . H18A H 0.2756 -0.1141 0.5064 0.056 Uiso 1 1 calc R . . H18B H 0.2902 -0.2442 0.4670 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02868(15) 0.02420(14) 0.02595(14) 0.00127(11) 0.01901(12) 0.00312(11) O1 0.0382(10) 0.0551(11) 0.0277(9) -0.0112(8) 0.0189(8) 0.0012(8) O2 0.0481(11) 0.0740(13) 0.0458(11) -0.0095(10) 0.0358(10) 0.0061(10) O3 0.0291(9) 0.0421(10) 0.0370(9) 0.0068(8) 0.0211(8) 0.0084(7) O4 0.0462(10) 0.0357(9) 0.0344(9) 0.0020(7) 0.0302(8) 0.0083(8) O5 0.0260(9) 0.0684(13) 0.0324(9) -0.0050(9) 0.0096(8) 0.0109(9) N1 0.0307(10) 0.0245(10) 0.0367(11) 0.0031(8) 0.0213(9) 0.0034(8) N2 0.0330(11) 0.0282(11) 0.0431(12) 0.0033(9) 0.0233(10) 0.0088(9) C1 0.0408(14) 0.0307(12) 0.0316(13) -0.0023(10) 0.0246(12) -0.0009(11) C2 0.0306(12) 0.0318(12) 0.0283(12) -0.0019(10) 0.0200(11) -0.0017(10) C3 0.0284(12) 0.0385(14) 0.0380(13) -0.0013(11) 0.0235(11) 0.0036(10) C4 0.0249(12) 0.0380(13) 0.0292(12) -0.0001(10) 0.0141(11) 0.0015(10) C5 0.0331(13) 0.0316(12) 0.0264(12) -0.0027(10) 0.0180(11) 0.0004(10) C6 0.0254(11) 0.0237(11) 0.0271(11) -0.0009(9) 0.0171(10) -0.0004(9) C7 0.0254(11) 0.0300(12) 0.0271(12) -0.0012(9) 0.0149(10) -0.0014(9) C8 0.0280(12) 0.0205(11) 0.0317(12) -0.0040(9) 0.0190(11) -0.0036(9) C9 0.0355(16) 0.134(3) 0.0458(18) 0.001(2) 0.0192(15) 0.0333(19) C10 0.0274(12) 0.0277(12) 0.0291(12) 0.0022(9) 0.0140(10) 0.0020(9) C11 0.0319(13) 0.0282(12) 0.0347(13) -0.0003(10) 0.0166(11) 0.0020(10) C12 0.0482(17) 0.0277(14) 0.0587(18) -0.0034(12) 0.0253(15) -0.0013(12) C13 0.0484(18) 0.0358(16) 0.073(2) -0.0052(15) 0.0280(16) -0.0141(14) C14 0.0343(15) 0.0521(18) 0.069(2) 0.0010(15) 0.0262(15) -0.0123(13) C15 0.0305(13) 0.0392(14) 0.0506(16) 0.0039(12) 0.0225(13) 0.0022(11) C16 0.0341(13) 0.0287(12) 0.0410(14) 0.0050(11) 0.0250(12) 0.0037(10) C17 0.0500(16) 0.0410(15) 0.0566(17) 0.0085(12) 0.0386(14) 0.0193(12) C18 0.0426(15) 0.0425(15) 0.0646(17) 0.0095(13) 0.0374(14) 0.0149(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9114(15) . ? Zn1 O4 1.9484(15) 6_565 ? Zn1 N1 1.9782(18) . ? Zn1 O3 1.9910(15) 5_566 ? O1 C1 1.284(3) . ? O2 C1 1.224(3) . ? O3 C8 1.255(3) . ? O3 Zn1 1.9910(15) 5_566 ? O4 C8 1.260(3) . ? O4 Zn1 1.9484(15) 6_566 ? O5 C4 1.370(3) . ? O5 C9 1.406(3) . ? N1 C16 1.325(3) . ? N1 C10 1.387(3) . ? N2 C16 1.338(3) . ? N2 C11 1.382(3) . ? N2 C17 1.470(3) . ? C1 C2 1.509(3) . ? C2 C7 1.388(3) . ? C2 C3 1.393(3) . ? C3 C4 1.382(3) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(3) . ? C6 C8 1.499(3) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.388(3) . ? C10 C11 1.390(3) . ? C11 C12 1.393(3) . ? C12 C13 1.368(4) . ? C12 H12 0.9300 . ? C13 C14 1.394(4) . ? C13 H13 0.9300 . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.509(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C18 1.512(5) 7_546 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 O4 111.59(7) . 6_565 ? O1 Zn1 N1 120.77(8) . . ? O4 Zn1 N1 104.26(7) 6_565 . ? O1 Zn1 O3 94.93(7) . 5_566 ? O4 Zn1 O3 114.63(7) 6_565 5_566 ? N1 Zn1 O3 111.05(7) . 5_566 ? C1 O1 Zn1 116.95(14) . . ? C8 O3 Zn1 136.18(14) . 5_566 ? C8 O4 Zn1 130.58(15) . 6_566 ? C4 O5 C9 116.6(2) . . ? C16 N1 C10 105.23(18) . . ? C16 N1 Zn1 126.81(16) . . ? C10 N1 Zn1 127.95(15) . . ? C16 N2 C11 107.22(18) . . ? C16 N2 C17 125.8(2) . . ? C11 N2 C17 127.0(2) . . ? O2 C1 O1 125.4(2) . . ? O2 C1 C2 120.7(2) . . ? O1 C1 C2 113.98(19) . . ? C7 C2 C3 119.8(2) . . ? C7 C2 C1 121.5(2) . . ? C3 C2 C1 118.7(2) . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? O5 C4 C3 124.4(2) . . ? O5 C4 C5 115.6(2) . . ? C3 C4 C5 120.0(2) . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 120.66(19) . . ? C5 C6 C8 119.02(19) . . ? C7 C6 C8 120.22(19) . . ? C2 C7 C6 119.5(2) . . ? C2 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? O3 C8 O4 125.6(2) . . ? O3 C8 C6 118.25(19) . . ? O4 C8 C6 116.17(19) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C15 129.9(2) . . ? N1 C10 C11 109.09(19) . . ? C15 C10 C11 121.0(2) . . ? N2 C11 C10 105.70(19) . . ? N2 C11 C12 132.3(2) . . ? C10 C11 C12 122.0(2) . . ? C13 C12 C11 116.3(2) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? C12 C13 C14 122.2(3) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 121.4(3) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C10 117.1(2) . . ? C14 C15 H15 121.5 . . ? C10 C15 H15 121.5 . . ? N1 C16 N2 112.8(2) . . ? N1 C16 H16 123.6 . . ? N2 C16 H16 123.6 . . ? N2 C17 C18 113.4(2) . . ? N2 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? N2 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C18 114.8(3) . 7_546 ? C17 C18 H18A 108.6 . . ? C18 C18 H18A 108.6 7_546 . ? C17 C18 H18B 108.6 . . ? C18 C18 H18B 108.6 7_546 . ? H18A C18 H18B 107.5 . . ? 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 O4 Zn1 O1 C1 -63.60(19) 6_565 . . . ? N1 Zn1 O1 C1 59.36(19) . . . . ? O3 Zn1 O1 C1 177.46(17) 5_566 . . . ? O1 Zn1 N1 C16 -95.2(2) . . . . ? O4 Zn1 N1 C16 31.2(2) 6_565 . . . ? O3 Zn1 N1 C16 155.14(19) 5_566 . . . ? O1 Zn1 N1 C10 83.2(2) . . . . ? O4 Zn1 N1 C10 -150.44(18) 6_565 . . . ? O3 Zn1 N1 C10 -26.5(2) 5_566 . . . ? Zn1 O1 C1 O2 5.1(3) . . . . ? Zn1 O1 C1 C2 -174.46(14) . . . . ? O2 C1 C2 C7 166.9(2) . . . . ? O1 C1 C2 C7 -13.6(3) . . . . ? O2 C1 C2 C3 -14.5(3) . . . . ? O1 C1 C2 C3 165.1(2) . . . . ? C7 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C4 -179.1(2) . . . . ? C9 O5 C4 C3 -5.9(4) . . . . ? C9 O5 C4 C5 172.8(3) . . . . ? C2 C3 C4 O5 180.0(2) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? O5 C4 C5 C6 -179.7(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C4 C5 C6 C8 176.0(2) . . . . ? C3 C2 C7 C6 -0.9(3) . . . . ? C1 C2 C7 C6 177.8(2) . . . . ? C5 C6 C7 C2 1.3(3) . . . . ? C8 C6 C7 C2 -175.0(2) . . . . ? Zn1 O3 C8 O4 -37.3(3) 5_566 . . . ? Zn1 O3 C8 C6 141.64(17) 5_566 . . . ? Zn1 O4 C8 O3 -24.5(3) 6_566 . . . ? Zn1 O4 C8 C6 156.54(15) 6_566 . . . ? C5 C6 C8 O3 153.1(2) . . . . ? C7 C6 C8 O3 -30.5(3) . . . . ? C5 C6 C8 O4 -27.9(3) . . . . ? C7 C6 C8 O4 148.5(2) . . . . ? C16 N1 C10 C15 178.5(2) . . . . ? Zn1 N1 C10 C15 -0.1(4) . . . . ? C16 N1 C10 C11 -0.3(3) . . . . ? Zn1 N1 C10 C11 -178.98(15) . . . . ? C16 N2 C11 C10 0.6(3) . . . . ? C17 N2 C11 C10 -178.2(2) . . . . ? C16 N2 C11 C12 -177.3(3) . . . . ? C17 N2 C11 C12 3.9(4) . . . . ? N1 C10 C11 N2 -0.2(3) . . . . ? C15 C10 C11 N2 -179.2(2) . . . . ? N1 C10 C11 C12 178.0(2) . . . . ? C15 C10 C11 C12 -1.0(4) . . . . ? N2 C11 C12 C13 177.2(3) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C14 1.3(5) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C13 C14 C15 C10 -0.6(4) . . . . ? N1 C10 C15 C14 -177.3(2) . . . . ? C11 C10 C15 C14 1.4(4) . . . . ? C10 N1 C16 N2 0.8(3) . . . . ? Zn1 N1 C16 N2 179.44(15) . . . . ? C11 N2 C16 N1 -0.9(3) . . . . ? C17 N2 C16 N1 178.0(2) . . . . ? C16 N2 C17 C18 88.5(3) . . . . ? C11 N2 C17 C18 -92.8(3) . . . . ? N2 C17 C18 C18 65.1(4) . . . 7_546 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.051 # Attachment 'w6675.cif' data_w6675 _database_code_depnum_ccdc_archive 'CCDC 849774' #TrackingRef 'w6675.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N4 O5 Zn' _chemical_formula_weight 477.81 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 8.6436(16) _cell_length_b 14.894(3) _cell_length_c 17.462(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2247.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1307 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 20.10 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 1.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8424 _exptl_absorpt_correction_T_max 0.9149 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10806 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.49 _reflns_number_total 4020 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^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 4020 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.15129(5) 0.49787(5) 0.97851(10) 0.02867(15) Uani 1 1 d . . . O1 O 0.3252(7) 0.4215(3) 0.8396(4) 0.091(2) Uani 1 1 d . . . O2 O 0.2808(6) 0.5477(3) 0.8992(3) 0.0459(12) Uani 1 1 d . . . O3 O 0.6348(7) 0.4326(3) 0.5949(3) 0.0694(18) Uani 1 1 d . . . O4 O 0.7498(5) 0.5610(3) 0.5646(3) 0.0447(12) Uani 1 1 d . . . O5 O 0.5699(7) 0.7810(3) 0.7674(3) 0.0808(17) Uani 1 1 d . . . N1 N 0.0021(5) 0.3998(4) 0.9502(3) 0.0325(14) Uani 1 1 d . . . N2 N -0.1717(6) 0.3208(4) 0.8880(3) 0.0375(15) Uani 1 1 d . . . N3 N -0.5133(5) 0.1037(4) 0.5016(3) 0.0342(15) Uani 1 1 d . . . N4 N -0.3473(6) 0.1907(3) 0.5599(3) 0.0320(13) Uani 1 1 d . . . C1 C 0.3418(9) 0.5007(4) 0.8478(6) 0.033(3) Uani 1 1 d . . . C2 C 0.4419(8) 0.5521(4) 0.7910(4) 0.0322(15) Uani 1 1 d . . . C3 C 0.5053(13) 0.5102(3) 0.7274(7) 0.0329(10) Uani 1 1 d . . . H3 H 0.4891 0.4491 0.7199 0.039 Uiso 1 1 calc R . . C4 C 0.5923(7) 0.5583(4) 0.6752(4) 0.0332(16) Uani 1 1 d . . . C5 C 0.6147(7) 0.6499(4) 0.6867(4) 0.0466(16) Uani 1 1 d . . . H5 H 0.6709 0.6833 0.6513 0.056 Uiso 1 1 calc R . . C6 C 0.5534(8) 0.6909(4) 0.7505(3) 0.0513(17) Uani 1 1 d . . . C7 C 0.4652(7) 0.6424(4) 0.8020(3) 0.0438(15) Uani 1 1 d . . . H7 H 0.4215 0.6710 0.8441 0.053 Uiso 1 1 calc R . . C8 C 0.6623(11) 0.5128(6) 0.6078(6) 0.045(3) Uani 1 1 d . . . C9 C 0.6089(10) 0.8393(4) 0.7092(4) 0.085(3) Uani 1 1 d . . . H9A H 0.5326 0.8360 0.6694 0.128 Uiso 1 1 calc R . . H9B H 0.7082 0.8230 0.6889 0.128 Uiso 1 1 calc R . . H9C H 0.6132 0.8994 0.7289 0.128 Uiso 1 1 calc R . . C10 C -0.0061(6) 0.3145(4) 0.9813(5) 0.0354(15) Uani 1 1 d . . . H10 H 0.0531 0.2935 1.0220 0.043 Uiso 1 1 calc R . . C11 C -0.1122(8) 0.2673(5) 0.9437(4) 0.0448(19) Uani 1 1 d . . . H11 H -0.1407 0.2082 0.9537 0.054 Uiso 1 1 calc R . . C12 C -0.0982(8) 0.3999(4) 0.8948(4) 0.0369(17) Uani 1 1 d . . . C13 C -0.1331(11) 0.4790(5) 0.8432(6) 0.073(3) Uani 1 1 d . . . H13A H -0.0792 0.5311 0.8617 0.110 Uiso 1 1 calc R . . H13B H -0.2424 0.4905 0.8434 0.110 Uiso 1 1 calc R . . H13C H -0.0998 0.4658 0.7920 0.110 Uiso 1 1 calc R . . C14 C -0.2851(8) 0.2943(5) 0.8296(4) 0.0414(17) Uani 1 1 d . . . H14A H -0.3597 0.3422 0.8226 0.050 Uiso 1 1 calc R . . H14B H -0.3404 0.2413 0.8468 0.050 Uiso 1 1 calc R . . C15 C -0.2070(8) 0.2747(5) 0.7547(4) 0.0433(18) Uani 1 1 d . . . H15A H -0.1274 0.2298 0.7629 0.052 Uiso 1 1 calc R . . H15B H -0.1569 0.3289 0.7365 0.052 Uiso 1 1 calc R . . C16 C -0.3177(8) 0.2412(5) 0.6935(4) 0.0372(16) Uani 1 1 d . . . H16A H -0.3662 0.1862 0.7112 0.045 Uiso 1 1 calc R . . H16B H -0.3985 0.2855 0.6859 0.045 Uiso 1 1 calc R . . C17 C -0.2380(8) 0.2233(5) 0.6176(4) 0.0424(18) Uani 1 1 d . . . H17A H -0.1901 0.2783 0.5994 0.051 Uiso 1 1 calc R . . H17B H -0.1570 0.1791 0.6249 0.051 Uiso 1 1 calc R . . C18 C -0.4119(8) 0.2418(4) 0.5031(3) 0.0384(17) Uani 1 1 d . . . H18 H -0.3905 0.3015 0.4917 0.046 Uiso 1 1 calc R . . C19 C -0.5140(7) 0.1867(4) 0.4666(4) 0.0360(18) Uani 1 1 d . . . H19 H -0.5747 0.2025 0.4248 0.043 Uiso 1 1 calc R . . C20 C -0.4098(8) 0.1086(4) 0.5580(4) 0.0377(17) Uani 1 1 d . . . C21 C -0.3692(10) 0.0337(5) 0.6093(5) 0.064(3) Uani 1 1 d . . . H21A H -0.2920 -0.0032 0.5853 0.096 Uiso 1 1 calc R . . H21B H -0.4598 -0.0017 0.6194 0.096 Uiso 1 1 calc R . . H21C H -0.3294 0.0571 0.6565 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0334(3) 0.0295(2) 0.0231(3) -0.0012(2) -0.0013(6) 0.0009(4) O1 0.152(6) 0.031(3) 0.090(5) -0.007(3) 0.079(4) -0.020(3) O2 0.058(3) 0.041(2) 0.039(3) -0.002(2) 0.023(3) -0.004(2) O3 0.102(4) 0.048(3) 0.059(4) -0.016(3) 0.041(3) -0.021(3) O4 0.053(3) 0.047(3) 0.033(3) -0.002(2) 0.021(2) -0.010(2) O5 0.151(5) 0.039(2) 0.052(3) -0.012(2) 0.034(3) -0.029(3) N1 0.035(4) 0.040(3) 0.023(3) -0.004(2) -0.002(2) -0.003(2) N2 0.036(3) 0.047(3) 0.030(3) -0.007(3) -0.005(3) -0.003(3) N3 0.038(3) 0.031(3) 0.033(4) -0.001(2) -0.006(3) 0.000(2) N4 0.040(3) 0.033(3) 0.023(3) 0.001(2) -0.005(3) -0.012(2) C1 0.036(5) 0.034(5) 0.030(6) 0.006(3) 0.020(4) 0.003(3) C2 0.037(3) 0.030(3) 0.029(4) 0.004(3) 0.000(3) 0.000(3) C3 0.035(2) 0.030(2) 0.033(2) -0.002(4) 0.0040(19) 0.007(3) C4 0.034(4) 0.038(4) 0.028(4) -0.001(3) 0.007(3) 0.000(3) C5 0.064(5) 0.040(3) 0.036(4) 0.004(3) 0.016(3) -0.016(3) C6 0.082(5) 0.034(3) 0.038(4) -0.007(3) 0.010(3) -0.012(3) C7 0.062(4) 0.043(3) 0.026(3) 0.001(3) 0.010(3) -0.002(3) C8 0.059(7) 0.042(5) 0.035(7) -0.003(4) -0.004(4) 0.002(4) C9 0.143(8) 0.046(4) 0.066(6) 0.001(4) 0.007(5) -0.015(5) C10 0.043(4) 0.035(3) 0.029(3) 0.004(4) -0.010(4) -0.003(3) C11 0.050(5) 0.039(4) 0.045(5) -0.002(3) 0.005(3) -0.015(3) C12 0.045(4) 0.037(4) 0.029(4) -0.003(3) -0.011(4) -0.005(3) C13 0.093(8) 0.055(5) 0.071(7) 0.017(5) -0.045(6) -0.004(5) C14 0.032(4) 0.056(4) 0.036(4) -0.009(3) -0.001(3) -0.015(3) C15 0.031(3) 0.060(4) 0.039(4) -0.015(3) -0.002(3) -0.009(3) C16 0.035(4) 0.043(4) 0.034(4) -0.005(3) -0.005(3) -0.012(3) C17 0.036(4) 0.050(4) 0.041(4) -0.008(3) -0.006(3) -0.006(3) C18 0.057(4) 0.030(3) 0.029(4) 0.004(3) 0.001(3) -0.007(3) C19 0.042(4) 0.038(3) 0.028(5) 0.001(3) -0.002(3) 0.002(3) C20 0.041(4) 0.036(4) 0.036(4) -0.001(3) -0.001(4) -0.003(3) C21 0.083(7) 0.043(4) 0.065(7) 0.004(5) -0.030(5) -0.011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.929(5) . ? Zn1 O4 1.939(5) 2_665 ? Zn1 N1 2.010(5) . ? Zn1 N3 2.017(5) 4_455 ? O1 C1 1.198(7) . ? O2 C1 1.254(10) . ? O3 C8 1.239(9) . ? O4 C8 1.287(11) . ? O4 Zn1 1.939(5) 2_664 ? O5 C9 1.377(7) . ? O5 C6 1.381(6) . ? N1 C12 1.299(7) . ? N1 C10 1.384(8) . ? N2 C12 1.343(7) . ? N2 C11 1.358(8) . ? N2 C14 1.469(8) . ? N3 C20 1.332(8) . ? N3 C19 1.379(8) . ? N3 Zn1 2.017(5) 4_444 ? N4 C20 1.337(7) . ? N4 C18 1.369(8) . ? N4 C17 1.464(8) . ? C1 C2 1.522(10) . ? C2 C7 1.374(8) . ? C2 C3 1.386(12) . ? C3 C4 1.382(12) . ? C3 H3 0.9300 . ? C4 C5 1.393(8) . ? C4 C8 1.487(12) . ? C5 C6 1.376(8) . ? C5 H5 0.9300 . ? C6 C7 1.382(8) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.329(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.514(10) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.500(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.518(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.518(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.363(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.473(10) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 118.33(17) . 2_665 ? O2 Zn1 N1 118.4(2) . . ? O4 Zn1 N1 98.3(2) 2_665 . ? O2 Zn1 N3 100.7(2) . 4_455 ? O4 Zn1 N3 117.3(2) 2_665 4_455 ? N1 Zn1 N3 103.73(14) . 4_455 ? C1 O2 Zn1 122.9(4) . . ? C8 O4 Zn1 117.4(5) . 2_664 ? C9 O5 C6 118.7(5) . . ? C12 N1 C10 105.0(6) . . ? C12 N1 Zn1 127.7(5) . . ? C10 N1 Zn1 127.1(4) . . ? C12 N2 C11 105.8(6) . . ? C12 N2 C14 127.8(6) . . ? C11 N2 C14 126.3(6) . . ? C20 N3 C19 106.3(5) . . ? C20 N3 Zn1 126.0(4) . 4_444 ? C19 N3 Zn1 127.5(4) . 4_444 ? C20 N4 C18 109.0(6) . . ? C20 N4 C17 125.5(6) . . ? C18 N4 C17 125.3(5) . . ? O1 C1 O2 125.8(8) . . ? O1 C1 C2 119.0(8) . . ? O2 C1 C2 115.2(5) . . ? C7 C2 C3 119.7(6) . . ? C7 C2 C1 119.0(6) . . ? C3 C2 C1 121.3(6) . . ? C4 C3 C2 120.7(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.2(6) . . ? C3 C4 C8 120.5(7) . . ? C5 C4 C8 120.3(7) . . ? C6 C5 C4 119.8(6) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 O5 124.3(5) . . ? C5 C6 C7 120.5(5) . . ? O5 C6 C7 115.2(5) . . ? C2 C7 C6 120.1(6) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? O3 C8 O4 123.1(9) . . ? O3 C8 C4 120.3(9) . . ? O4 C8 C4 116.6(7) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 109.1(7) . . ? C11 C10 H10 125.4 . . ? N1 C10 H10 125.4 . . ? C10 C11 N2 107.7(6) . . ? C10 C11 H11 126.1 . . ? N2 C11 H11 126.1 . . ? N1 C12 N2 112.4(6) . . ? N1 C12 C13 125.2(6) . . ? N2 C12 C13 122.4(6) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C15 110.9(5) . . ? N2 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C16 113.2(5) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.8 . . ? C17 C16 C15 112.7(4) . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C15 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? N4 C17 C16 111.5(6) . . ? N4 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? N4 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C19 C18 N4 105.5(6) . . ? C19 C18 H18 127.2 . . ? N4 C18 H18 127.2 . . ? C18 C19 N3 109.2(6) . . ? C18 C19 H19 125.4 . . ? N3 C19 H19 125.4 . . ? N3 C20 N4 109.9(6) . . ? N3 C20 C21 124.6(6) . . ? N4 C20 C21 125.6(7) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 O4 Zn1 O2 C1 79.0(7) 2_665 . . . ? N1 Zn1 O2 C1 -39.5(7) . . . . ? N3 Zn1 O2 C1 -151.7(7) 4_455 . . . ? O2 Zn1 N1 C12 -51.0(6) . . . . ? O4 Zn1 N1 C12 -179.7(5) 2_665 . . . ? N3 Zn1 N1 C12 59.5(6) 4_455 . . . ? O2 Zn1 N1 C10 122.6(5) . . . . ? O4 Zn1 N1 C10 -6.1(6) 2_665 . . . ? N3 Zn1 N1 C10 -127.0(5) 4_455 . . . ? Zn1 O2 C1 O1 2.3(15) . . . . ? Zn1 O2 C1 C2 -179.2(5) . . . . ? O1 C1 C2 C7 -177.8(9) . . . . ? O2 C1 C2 C7 3.6(11) . . . . ? O1 C1 C2 C3 4.3(13) . . . . ? O2 C1 C2 C3 -174.3(9) . . . . ? C7 C2 C3 C4 0.3(14) . . . . ? C1 C2 C3 C4 178.2(7) . . . . ? C2 C3 C4 C5 -0.6(13) . . . . ? C2 C3 C4 C8 179.0(8) . . . . ? C3 C4 C5 C6 1.5(10) . . . . ? C8 C4 C5 C6 -178.0(7) . . . . ? C4 C5 C6 O5 179.6(6) . . . . ? C4 C5 C6 C7 -2.3(9) . . . . ? C9 O5 C6 C5 19.6(10) . . . . ? C9 O5 C6 C7 -158.6(7) . . . . ? C3 C2 C7 C6 -1.0(11) . . . . ? C1 C2 C7 C6 -178.9(6) . . . . ? C5 C6 C7 C2 2.0(9) . . . . ? O5 C6 C7 C2 -179.7(6) . . . . ? Zn1 O4 C8 O3 -2.7(12) 2_664 . . . ? Zn1 O4 C8 C4 177.7(5) 2_664 . . . ? C3 C4 C8 O3 4.8(13) . . . . ? C5 C4 C8 O3 -175.6(8) . . . . ? C3 C4 C8 O4 -175.6(8) . . . . ? C5 C4 C8 O4 4.0(11) . . . . ? C12 N1 C10 C11 -0.7(7) . . . . ? Zn1 N1 C10 C11 -175.4(4) . . . . ? N1 C10 C11 N2 0.7(8) . . . . ? C12 N2 C11 C10 -0.4(8) . . . . ? C14 N2 C11 C10 175.8(6) . . . . ? C10 N1 C12 N2 0.4(7) . . . . ? Zn1 N1 C12 N2 175.2(4) . . . . ? C10 N1 C12 C13 179.6(8) . . . . ? Zn1 N1 C12 C13 -5.7(11) . . . . ? C11 N2 C12 N1 -0.1(8) . . . . ? C14 N2 C12 N1 -176.1(6) . . . . ? C11 N2 C12 C13 -179.2(8) . . . . ? C14 N2 C12 C13 4.7(12) . . . . ? C12 N2 C14 C15 75.5(8) . . . . ? C11 N2 C14 C15 -99.8(8) . . . . ? N2 C14 C15 C16 176.3(5) . . . . ? C14 C15 C16 C17 178.9(7) . . . . ? C20 N4 C17 C16 -73.5(9) . . . . ? C18 N4 C17 C16 100.5(8) . . . . ? C15 C16 C17 N4 179.7(5) . . . . ? C20 N4 C18 C19 -0.7(8) . . . . ? C17 N4 C18 C19 -175.6(5) . . . . ? N4 C18 C19 N3 0.9(7) . . . . ? C20 N3 C19 C18 -0.9(7) . . . . ? Zn1 N3 C19 C18 175.0(4) 4_444 . . . ? C19 N3 C20 N4 0.4(7) . . . . ? Zn1 N3 C20 N4 -175.5(4) 4_444 . . . ? C19 N3 C20 C21 -178.6(7) . . . . ? Zn1 N3 C20 C21 5.6(10) 4_444 . . . ? C18 N4 C20 N3 0.2(8) . . . . ? C17 N4 C20 N3 175.0(6) . . . . ? C18 N4 C20 C21 179.1(7) . . . . ? C17 N4 C20 C21 -6.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.428 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.065 # Attachment 'x0027.cif' data_x0027 _database_code_depnum_ccdc_archive 'CCDC 849775' #TrackingRef 'x0027.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N2 O5 Zn' _chemical_formula_weight 340.61 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3071(10) _cell_length_b 8.3924(11) _cell_length_c 10.1349(13) _cell_angle_alpha 99.4450(10) _cell_angle_beta 101.3820(10) _cell_angle_gamma 106.4880(10) _cell_volume 645.72(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2927 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.752 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 1.926 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6456 _exptl_absorpt_correction_T_max 0.7689 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4925 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2384 _reflns_number_gt 2178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.3506P] 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 2384 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.65964(3) 0.46582(3) 0.88912(2) 0.02226(9) Uani 1 1 d . . . O1 O 0.82378(19) 0.60119(19) 0.79811(14) 0.0298(3) Uani 1 1 d . . . O2 O 0.6325(2) 0.3832(2) 0.63784(16) 0.0333(4) Uani 1 1 d . . . O3 O 0.55023(17) 0.46797(18) 0.14926(14) 0.0250(3) Uani 1 1 d . . . O4 O 0.78850(19) 0.59564(19) 0.08825(14) 0.0289(3) Uani 1 1 d . . . O5 O 1.2214(2) 0.9221(2) 0.55561(15) 0.0362(4) Uani 1 1 d . . . N1 N 0.6665(2) 0.2348(2) 0.90821(17) 0.0250(4) Uani 1 1 d . . . N2 N 0.7939(2) 0.0541(2) 0.97258(19) 0.0297(4) Uani 1 1 d . . . C1 C 0.5601(3) 0.0710(3) 0.8418(2) 0.0310(5) Uani 1 1 d . . . H1 H 0.4519 0.0422 0.7797 0.037 Uiso 1 1 calc R . . C2 C 0.6371(3) -0.0412(3) 0.8808(2) 0.0357(5) Uani 1 1 d . . . H2 H 0.5928 -0.1597 0.8514 0.043 Uiso 1 1 calc R . . C3 C 0.8063(3) 0.2191(3) 0.9864(2) 0.0285(5) Uani 1 1 d . . . H3 H 0.9003 0.3101 1.0432 0.034 Uiso 1 1 calc R . . C4 C 0.9305(3) -0.0080(3) 1.0388(2) 0.0348(5) Uani 1 1 d . . . H4A H 0.8799 -0.1267 1.0406 0.042 Uiso 1 1 calc R . . H4B H 0.9819 0.0579 1.1336 0.042 Uiso 1 1 calc R . . C5 C 0.7574(3) 0.5167(3) 0.6709(2) 0.0235(4) Uani 1 1 d . . . C6 C 0.8359(3) 0.5915(3) 0.5642(2) 0.0219(4) Uani 1 1 d . . . C7 C 0.9972(3) 0.7173(3) 0.6026(2) 0.0246(4) Uani 1 1 d . . . H7 H 1.0608 0.7508 0.6947 0.030 Uiso 1 1 calc R . . C8 C 1.0657(3) 0.7944(3) 0.5049(2) 0.0247(4) Uani 1 1 d . . . C9 C 0.9738(3) 0.7394(3) 0.3664(2) 0.0249(4) Uani 1 1 d . . . H9 H 1.0206 0.7864 0.2999 0.030 Uiso 1 1 calc R . . C10 C 0.8108(3) 0.6130(3) 0.3276(2) 0.0214(4) Uani 1 1 d . . . C11 C 0.7413(3) 0.5391(3) 0.4257(2) 0.0228(4) Uani 1 1 d . . . H11 H 0.6325 0.4552 0.3992 0.027 Uiso 1 1 calc R . . C12 C 1.2886(3) 1.0123(3) 0.4604(3) 0.0363(6) Uani 1 1 d . . . H12A H 1.3158 0.9363 0.3931 0.054 Uiso 1 1 calc R . . H12B H 1.3919 1.1058 0.5094 0.054 Uiso 1 1 calc R . . H12C H 1.2033 1.0554 0.4143 0.054 Uiso 1 1 calc R . . C13 C 0.7098(3) 0.5564(3) 0.1787(2) 0.0207(4) 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 0.02313(14) 0.02606(15) 0.01929(13) 0.00899(10) 0.00596(9) 0.00823(10) O1 0.0305(8) 0.0389(9) 0.0153(7) 0.0064(6) 0.0065(6) 0.0038(7) O2 0.0333(9) 0.0332(9) 0.0271(8) 0.0098(7) 0.0073(7) 0.0001(7) O3 0.0204(7) 0.0292(8) 0.0231(8) 0.0072(6) 0.0005(6) 0.0075(6) O4 0.0323(8) 0.0339(8) 0.0153(7) 0.0073(6) 0.0049(6) 0.0031(7) O5 0.0287(8) 0.0411(10) 0.0244(8) 0.0056(7) 0.0016(7) -0.0055(7) N1 0.0266(9) 0.0262(10) 0.0223(9) 0.0079(8) 0.0043(7) 0.0089(8) N2 0.0352(10) 0.0265(10) 0.0311(10) 0.0117(8) 0.0071(8) 0.0136(8) C1 0.0286(12) 0.0320(12) 0.0262(12) 0.0054(10) 0.0014(9) 0.0052(10) C2 0.0419(14) 0.0235(12) 0.0355(13) 0.0043(10) 0.0076(11) 0.0046(10) C3 0.0292(11) 0.0251(12) 0.0291(12) 0.0072(9) 0.0028(9) 0.0085(9) C4 0.0458(14) 0.0343(13) 0.0320(13) 0.0153(10) 0.0081(11) 0.0221(11) C5 0.0234(11) 0.0323(12) 0.0199(10) 0.0101(9) 0.0072(8) 0.0134(10) C6 0.0238(10) 0.0260(11) 0.0174(10) 0.0058(8) 0.0055(8) 0.0100(9) C7 0.0261(11) 0.0326(12) 0.0142(10) 0.0046(9) 0.0033(8) 0.0099(9) C8 0.0210(10) 0.0269(11) 0.0217(10) 0.0028(9) 0.0032(8) 0.0043(9) C9 0.0259(11) 0.0293(11) 0.0206(10) 0.0094(9) 0.0081(8) 0.0073(9) C10 0.0232(10) 0.0267(11) 0.0151(10) 0.0057(8) 0.0034(8) 0.0098(9) C11 0.0224(10) 0.0253(11) 0.0198(10) 0.0052(8) 0.0040(8) 0.0076(9) C12 0.0278(12) 0.0345(13) 0.0409(14) 0.0132(11) 0.0071(10) 0.0005(10) C13 0.0269(11) 0.0209(10) 0.0178(10) 0.0073(8) 0.0053(8) 0.0117(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.9629(14) 2_666 ? Zn1 O1 1.9903(15) . ? Zn1 N1 1.9949(17) . ? Zn1 O4 2.0419(14) 1_556 ? Zn1 O2 2.4743(16) . ? Zn1 C5 2.560(2) . ? O1 C5 1.291(2) . ? O2 C5 1.234(3) . ? O3 C13 1.269(2) . ? O3 Zn1 1.9629(14) 2_666 ? O4 C13 1.261(2) . ? O4 Zn1 2.0419(14) 1_554 ? O5 C8 1.363(2) . ? O5 C12 1.424(3) . ? N1 C3 1.324(3) . ? N1 C1 1.377(3) . ? N2 C3 1.341(3) . ? N2 C2 1.374(3) . ? N2 C4 1.469(3) . ? C1 C2 1.348(3) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C4 1.508(5) 2_757 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.503(3) . ? C6 C7 1.385(3) . ? C6 C11 1.395(3) . ? C7 C8 1.395(3) . ? C7 H7 0.9300 . ? C8 C9 1.389(3) . ? C9 C10 1.397(3) . ? C9 H9 0.9300 . ? C10 C11 1.390(3) . ? C10 C13 1.499(3) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 106.29(6) 2_666 . ? O3 Zn1 N1 125.80(7) 2_666 . ? O1 Zn1 N1 119.29(7) . . ? O3 Zn1 O4 104.65(6) 2_666 1_556 ? O1 Zn1 O4 96.93(6) . 1_556 ? N1 Zn1 O4 97.70(7) . 1_556 ? O3 Zn1 O2 90.16(6) 2_666 . ? O1 Zn1 O2 58.01(5) . . ? N1 Zn1 O2 90.30(6) . . ? O4 Zn1 O2 154.06(6) 1_556 . ? O3 Zn1 C5 98.07(6) 2_666 . ? O1 Zn1 C5 29.73(6) . . ? N1 Zn1 C5 106.99(7) . . ? O4 Zn1 C5 126.53(6) 1_556 . ? O2 Zn1 C5 28.32(6) . . ? C5 O1 Zn1 100.40(12) . . ? C5 O2 Zn1 79.72(12) . . ? C13 O3 Zn1 130.94(13) . 2_666 ? C13 O4 Zn1 115.42(13) . 1_554 ? C8 O5 C12 117.13(17) . . ? C3 N1 C1 105.97(18) . . ? C3 N1 Zn1 119.99(14) . . ? C1 N1 Zn1 133.51(14) . . ? C3 N2 C2 107.39(18) . . ? C3 N2 C4 124.90(19) . . ? C2 N2 C4 127.61(19) . . ? C2 C1 N1 109.4(2) . . ? C2 C1 H1 125.3 . . ? N1 C1 H1 125.3 . . ? C1 C2 N2 106.5(2) . . ? C1 C2 H2 126.8 . . ? N2 C2 H2 126.8 . . ? N1 C3 N2 110.82(19) . . ? N1 C3 H3 124.6 . . ? N2 C3 H3 124.6 . . ? N2 C4 C4 110.6(2) . 2_757 ? N2 C4 H4A 109.5 . . ? C4 C4 H4A 109.5 2_757 . ? N2 C4 H4B 109.5 . . ? C4 C4 H4B 109.5 2_757 . ? H4A C4 H4B 108.1 . . ? O2 C5 O1 121.71(19) . . ? O2 C5 C6 121.45(18) . . ? O1 C5 C6 116.81(18) . . ? O2 C5 Zn1 71.96(11) . . ? O1 C5 Zn1 49.87(10) . . ? C6 C5 Zn1 165.67(15) . . ? C7 C6 C11 119.73(19) . . ? C7 C6 C5 120.77(18) . . ? C11 C6 C5 119.43(18) . . ? C6 C7 C8 120.89(18) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? O5 C8 C9 124.80(19) . . ? O5 C8 C7 115.71(18) . . ? C9 C8 C7 119.50(19) . . ? C8 C9 C10 119.62(19) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 120.68(18) . . ? C11 C10 C13 119.65(18) . . ? C9 C10 C13 119.67(18) . . ? C10 C11 C6 119.52(19) . . ? C10 C11 H11 120.2 . . ? C6 C11 H11 120.2 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 O3 123.08(18) . . ? O4 C13 C10 118.38(18) . . ? O3 C13 C10 118.52(17) . . ? 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 O3 Zn1 O1 C5 -77.47(13) 2_666 . . . ? N1 Zn1 O1 C5 72.14(14) . . . . ? O4 Zn1 O1 C5 175.02(12) 1_556 . . . ? O2 Zn1 O1 C5 2.21(11) . . . . ? O3 Zn1 O2 C5 106.89(12) 2_666 . . . ? O1 Zn1 O2 C5 -2.32(12) . . . . ? N1 Zn1 O2 C5 -127.31(13) . . . . ? O4 Zn1 O2 C5 -18.8(2) 1_556 . . . ? O3 Zn1 N1 C3 -152.17(15) 2_666 . . . ? O1 Zn1 N1 C3 64.61(18) . . . . ? O4 Zn1 N1 C3 -37.83(17) 1_556 . . . ? O2 Zn1 N1 C3 117.41(17) . . . . ? C5 Zn1 N1 C3 94.18(17) . . . . ? O3 Zn1 N1 C1 37.5(2) 2_666 . . . ? O1 Zn1 N1 C1 -105.7(2) . . . . ? O4 Zn1 N1 C1 151.9(2) 1_556 . . . ? O2 Zn1 N1 C1 -52.9(2) . . . . ? C5 Zn1 N1 C1 -76.1(2) . . . . ? C3 N1 C1 C2 0.0(3) . . . . ? Zn1 N1 C1 C2 171.25(16) . . . . ? N1 C1 C2 N2 -0.1(3) . . . . ? C3 N2 C2 C1 0.2(3) . . . . ? C4 N2 C2 C1 -176.4(2) . . . . ? C1 N1 C3 N2 0.2(2) . . . . ? Zn1 N1 C3 N2 -172.53(14) . . . . ? C2 N2 C3 N1 -0.2(3) . . . . ? C4 N2 C3 N1 176.46(19) . . . . ? C3 N2 C4 C4 -78.7(3) . . . 2_757 ? C2 N2 C4 C4 97.3(3) . . . 2_757 ? Zn1 O2 C5 O1 3.56(18) . . . . ? Zn1 O2 C5 C6 -174.43(18) . . . . ? Zn1 O1 C5 O2 -4.4(2) . . . . ? Zn1 O1 C5 C6 173.65(14) . . . . ? O3 Zn1 C5 O2 -75.11(12) 2_666 . . . ? O1 Zn1 C5 O2 176.0(2) . . . . ? N1 Zn1 C5 O2 56.27(13) . . . . ? O4 Zn1 C5 O2 169.88(11) 1_556 . . . ? O3 Zn1 C5 O1 108.85(13) 2_666 . . . ? N1 Zn1 C5 O1 -119.77(13) . . . . ? O4 Zn1 C5 O1 -6.16(15) 1_556 . . . ? O2 Zn1 C5 O1 -176.0(2) . . . . ? O3 Zn1 C5 C6 85.3(6) 2_666 . . . ? O1 Zn1 C5 C6 -23.5(5) . . . . ? N1 Zn1 C5 C6 -143.3(5) . . . . ? O4 Zn1 C5 C6 -29.7(6) 1_556 . . . ? O2 Zn1 C5 C6 160.4(6) . . . . ? O2 C5 C6 C7 -165.4(2) . . . . ? O1 C5 C6 C7 16.5(3) . . . . ? Zn1 C5 C6 C7 36.5(6) . . . . ? O2 C5 C6 C11 17.6(3) . . . . ? O1 C5 C6 C11 -160.45(19) . . . . ? Zn1 C5 C6 C11 -140.5(5) . . . . ? C11 C6 C7 C8 0.9(3) . . . . ? C5 C6 C7 C8 -176.03(18) . . . . ? C12 O5 C8 C9 4.2(3) . . . . ? C12 O5 C8 C7 -175.34(19) . . . . ? C6 C7 C8 O5 176.95(19) . . . . ? C6 C7 C8 C9 -2.6(3) . . . . ? O5 C8 C9 C10 -176.7(2) . . . . ? C7 C8 C9 C10 2.8(3) . . . . ? C8 C9 C10 C11 -1.5(3) . . . . ? C8 C9 C10 C13 178.62(19) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? C13 C10 C11 C6 179.72(18) . . . . ? C7 C6 C11 C10 0.5(3) . . . . ? C5 C6 C11 C10 177.46(18) . . . . ? Zn1 O4 C13 O3 -12.9(2) 1_554 . . . ? Zn1 O4 C13 C10 165.41(13) 1_554 . . . ? Zn1 O3 C13 O4 -83.3(2) 2_666 . . . ? Zn1 O3 C13 C10 98.4(2) 2_666 . . . ? C11 C10 C13 O4 -164.53(18) . . . . ? C9 C10 C13 O4 15.4(3) . . . . ? C11 C10 C13 O3 13.9(3) . . . . ? C9 C10 C13 O3 -166.24(18) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.293 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.054 # Attachment 'x0028.cif' data_x0028 _database_code_depnum_ccdc_archive 'CCDC 849776' #TrackingRef 'x0028.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H38 N12 O11 Zn2' _chemical_formula_weight 1017.58 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1320(17) _cell_length_b 10.4262(17) _cell_length_c 11.8021(19) _cell_angle_alpha 72.703(2) _cell_angle_beta 82.516(2) _cell_angle_gamma 64.173(2) _cell_volume 1071.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2052 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 23.25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.196 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7237 _exptl_absorpt_correction_T_max 0.8648 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8003 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3948 _reflns_number_gt 3151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+1.0109P] 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 3948 _refine_ls_number_parameters 308 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.078 _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 0.55147(4) 0.73350(5) 0.64551(4) 0.02770(16) Uani 1 1 d . . . O1 O 0.6427(3) 0.8675(3) 0.6491(2) 0.0379(7) Uani 1 1 d . . . O2 O 0.8444(3) 0.6609(4) 0.6932(3) 0.0610(10) Uani 1 1 d . . . O3 O 1.3262(3) 0.6905(3) 0.6158(3) 0.0375(7) Uani 1 1 d . . . O4 O 1.3434(3) 0.8758(3) 0.6569(2) 0.0303(6) Uani 1 1 d . . . O5 O 0.8128(3) 1.2574(3) 0.6468(3) 0.0445(7) Uani 1 1 d . . . O6 O 0.0673(7) 0.4935(7) 0.8772(8) 0.074(2) Uani 0.50 1 d PU . . H1W H 0.0549 0.4747 0.8151 0.111 Uiso 0.50 1 d PR . . H2W H 0.0287 0.4603 0.9408 0.111 Uiso 0.50 1 d PR . . N1 N 0.5934(3) 0.5536(3) 0.7858(3) 0.0310(7) Uani 1 1 d . . . N2 N 0.6857(3) 0.3778(3) 0.9460(3) 0.0332(8) Uani 1 1 d . . . N3 N 0.6135(3) 0.7131(3) 0.4789(3) 0.0299(7) Uani 1 1 d . . . N4 N 0.6793(4) 0.7783(4) 0.2969(3) 0.0357(8) Uani 1 1 d . . . N5 N 0.5652(4) 0.3644(4) 0.9219(3) 0.0460(9) Uani 1 1 d . . . N6 N 0.6775(5) 0.6453(4) 0.3105(3) 0.0523(10) Uani 1 1 d . . . C1 C 0.7799(4) 0.7974(5) 0.6685(4) 0.0347(9) Uani 1 1 d . . . C2 C 0.8674(4) 0.8862(4) 0.6593(3) 0.0288(8) Uani 1 1 d . . . C3 C 1.0194(4) 0.8144(4) 0.6532(3) 0.0287(8) Uani 1 1 d . . . H3 H 1.0641 0.7147 0.6551 0.034 Uiso 1 1 calc R . . C4 C 1.1039(4) 0.8909(4) 0.6443(3) 0.0258(8) Uani 1 1 d . . . C5 C 1.0376(4) 1.0386(4) 0.6428(3) 0.0284(8) Uani 1 1 d . . . H5 H 1.0949 1.0895 0.6381 0.034 Uiso 1 1 calc R . . C6 C 0.8863(4) 1.1114(4) 0.6482(3) 0.0307(9) Uani 1 1 d . . . C7 C 0.8009(4) 1.0345(4) 0.6556(3) 0.0318(9) Uani 1 1 d . . . H7 H 0.6992 1.0830 0.6580 0.038 Uiso 1 1 calc R . . C8 C 1.2683(4) 0.8118(4) 0.6371(3) 0.0270(8) Uani 1 1 d . . . C9 C 0.8991(5) 1.3381(5) 0.6358(5) 0.0509(12) Uani 1 1 d . . . H9A H 0.9618 1.2969 0.7038 0.076 Uiso 1 1 calc R . . H9B H 0.8358 1.4399 0.6309 0.076 Uiso 1 1 calc R . . H9C H 0.9580 1.3318 0.5653 0.076 Uiso 1 1 calc R . . C10 C 0.5140(4) 0.4719(4) 0.8247(4) 0.0391(10) Uani 1 1 d . . . H10 H 0.4307 0.4906 0.7858 0.047 Uiso 1 1 calc R . . C11 C 0.7000(4) 0.4898(4) 0.8654(4) 0.0358(9) Uani 1 1 d . . . H11 H 0.7742 0.5198 0.8645 0.043 Uiso 1 1 calc R . . C12 C 0.7804(5) 0.2737(5) 1.0464(4) 0.0415(10) Uani 1 1 d . . . H12A H 0.7202 0.2477 1.1119 0.050 Uiso 1 1 calc R . . H12B H 0.8300 0.3219 1.0716 0.050 Uiso 1 1 calc R . . C13 C 0.8605(4) 0.0583(5) 0.9563(4) 0.0379(10) Uani 1 1 d . . . H13 H 0.7664 0.0973 0.9261 0.045 Uiso 1 1 calc R . . C14 C 0.8943(4) 0.1335(4) 1.0186(3) 0.0329(9) Uani 1 1 d . . . C15 C 1.0351(4) 0.0743(5) 1.0615(4) 0.0376(10) Uani 1 1 d . . . H15 H 1.0599 0.1240 1.1028 0.045 Uiso 1 1 calc R . . C16 C 0.6364(5) 0.6110(5) 0.4208(4) 0.0452(11) Uani 1 1 d . . . H16 H 0.6240 0.5245 0.4562 0.054 Uiso 1 1 calc R . . C17 C 0.6416(4) 0.8162(4) 0.3973(3) 0.0324(9) Uani 1 1 d . . . H17 H 0.6356 0.9029 0.4091 0.039 Uiso 1 1 calc R . . C18 C 0.7227(5) 0.8573(6) 0.1839(4) 0.0508(12) Uani 1 1 d . . . H18A H 0.8108 0.7881 0.1549 0.061 Uiso 1 1 calc R . . H18B H 0.7457 0.9326 0.1975 0.061 Uiso 1 1 calc R . . C19 C 0.6169(6) 0.8669(5) -0.0006(4) 0.0517(12) Uani 1 1 d . . . H19 H 0.6955 0.7774 -0.0024 0.062 Uiso 1 1 calc R . . C20 C 0.6050(5) 0.9296(5) 0.0903(3) 0.0391(10) Uani 1 1 d . . . C21 C 0.4892(5) 1.0623(6) 0.0898(4) 0.0509(12) Uani 1 1 d . . . H21 H 0.4810 1.1060 0.1501 0.061 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0209(2) 0.0300(3) 0.0301(3) -0.00600(18) -0.00016(17) -0.01009(18) O1 0.0252(14) 0.0553(18) 0.0447(17) -0.0207(14) 0.0023(12) -0.0232(14) O2 0.0377(18) 0.043(2) 0.103(3) -0.0078(19) -0.0024(18) -0.0246(16) O3 0.0286(14) 0.0301(15) 0.0538(18) -0.0156(13) -0.0036(13) -0.0086(12) O4 0.0190(12) 0.0301(14) 0.0453(16) -0.0111(12) 0.0004(11) -0.0129(11) O5 0.0288(15) 0.0341(16) 0.067(2) -0.0162(15) -0.0053(14) -0.0073(13) O6 0.048(4) 0.037(3) 0.111(5) 0.012(4) -0.033(4) -0.006(3) N1 0.0257(17) 0.0320(18) 0.0337(18) -0.0066(15) -0.0013(14) -0.0118(14) N2 0.0300(17) 0.0303(18) 0.0314(18) -0.0020(14) -0.0029(14) -0.0089(14) N3 0.0301(17) 0.0299(17) 0.0300(17) -0.0060(14) 0.0025(14) -0.0149(14) N4 0.0384(19) 0.044(2) 0.0268(18) -0.0057(16) -0.0014(15) -0.0218(17) N5 0.040(2) 0.044(2) 0.051(2) 0.0014(18) -0.0043(17) -0.0222(18) N6 0.077(3) 0.053(2) 0.039(2) -0.0182(19) 0.005(2) -0.036(2) C1 0.029(2) 0.049(3) 0.034(2) -0.0141(19) 0.0063(17) -0.023(2) C2 0.0248(19) 0.039(2) 0.026(2) -0.0074(17) 0.0005(15) -0.0168(17) C3 0.0269(19) 0.032(2) 0.028(2) -0.0054(17) -0.0008(16) -0.0147(17) C4 0.0231(18) 0.031(2) 0.0239(19) -0.0057(15) -0.0002(14) -0.0126(16) C5 0.0225(19) 0.032(2) 0.033(2) -0.0056(17) -0.0013(15) -0.0149(16) C6 0.0249(19) 0.031(2) 0.033(2) -0.0075(17) -0.0026(16) -0.0086(17) C7 0.0195(18) 0.044(2) 0.030(2) -0.0085(18) 0.0007(15) -0.0122(17) C8 0.0237(18) 0.031(2) 0.0254(19) -0.0013(16) -0.0016(15) -0.0137(16) C9 0.042(3) 0.037(2) 0.075(3) -0.021(2) -0.003(2) -0.013(2) C10 0.032(2) 0.036(2) 0.048(3) -0.001(2) -0.0084(19) -0.0176(19) C11 0.029(2) 0.038(2) 0.038(2) -0.0045(19) -0.0042(18) -0.0147(18) C12 0.045(3) 0.037(2) 0.029(2) -0.0005(18) -0.0059(19) -0.009(2) C13 0.033(2) 0.040(2) 0.034(2) -0.0029(19) -0.0062(18) -0.0118(19) C14 0.036(2) 0.033(2) 0.0220(19) -0.0001(16) -0.0014(16) -0.0112(18) C15 0.037(2) 0.040(2) 0.032(2) -0.0054(18) -0.0065(18) -0.0132(19) C16 0.066(3) 0.037(2) 0.043(3) -0.011(2) 0.002(2) -0.031(2) C17 0.035(2) 0.030(2) 0.034(2) -0.0056(17) -0.0023(17) -0.0166(18) C18 0.049(3) 0.074(3) 0.031(2) -0.001(2) -0.002(2) -0.034(3) C19 0.058(3) 0.049(3) 0.045(3) -0.015(2) -0.004(2) -0.017(2) C20 0.045(2) 0.055(3) 0.024(2) -0.0041(19) 0.0033(18) -0.032(2) C21 0.059(3) 0.067(3) 0.035(3) -0.024(2) -0.002(2) -0.027(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.995(3) . ? Zn1 O4 1.996(2) 1_455 ? Zn1 N1 2.020(3) . ? Zn1 N3 2.030(3) . ? O1 C1 1.272(5) . ? O2 C1 1.237(5) . ? O3 C8 1.230(4) . ? O4 C8 1.288(4) . ? O4 Zn1 1.996(2) 1_655 ? O5 C6 1.368(5) . ? O5 C9 1.427(5) . ? O6 H1W 0.8500 . ? O6 H2W 0.8500 . ? N1 C11 1.326(5) . ? N1 C10 1.361(5) . ? N2 C11 1.319(5) . ? N2 N5 1.362(5) . ? N2 C12 1.458(5) . ? N3 C17 1.320(5) . ? N3 C16 1.354(5) . ? N4 C17 1.317(5) . ? N4 N6 1.356(5) . ? N4 C18 1.470(5) . ? N5 C10 1.314(5) . ? N6 C16 1.307(6) . ? C1 C2 1.511(5) . ? C2 C7 1.380(5) . ? C2 C3 1.392(5) . ? C3 C4 1.378(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 C8 1.507(5) . ? C5 C6 1.385(5) . ? C5 H5 0.9300 . ? C6 C7 1.394(5) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C14 1.514(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.383(6) . ? C13 C15 1.384(6) 2_757 ? C13 H13 0.9300 . ? C14 C15 1.381(5) . ? C15 C13 1.384(6) 2_757 ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C20 1.508(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.381(6) . ? C19 C21 1.396(6) 2_675 ? C19 H19 0.9300 . ? C20 C21 1.369(6) . ? C21 C19 1.396(6) 2_675 ? C21 H21 0.9300 . ? 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 O4 96.88(11) . 1_455 ? O1 Zn1 N1 116.33(12) . . ? O4 Zn1 N1 108.07(12) 1_455 . ? O1 Zn1 N3 97.91(12) . . ? O4 Zn1 N3 113.70(12) 1_455 . ? N1 Zn1 N3 121.20(12) . . ? C1 O1 Zn1 111.9(3) . . ? C8 O4 Zn1 104.1(2) . 1_655 ? C6 O5 C9 117.0(3) . . ? H1W O6 H2W 116.7 . . ? C11 N1 C10 102.8(3) . . ? C11 N1 Zn1 129.1(3) . . ? C10 N1 Zn1 128.0(3) . . ? C11 N2 N5 109.9(3) . . ? C11 N2 C12 129.2(4) . . ? N5 N2 C12 120.9(3) . . ? C17 N3 C16 103.3(3) . . ? C17 N3 Zn1 121.3(3) . . ? C16 N3 Zn1 135.4(3) . . ? C17 N4 N6 109.8(3) . . ? C17 N4 C18 129.0(4) . . ? N6 N4 C18 121.2(4) . . ? C10 N5 N2 102.7(3) . . ? C16 N6 N4 103.1(3) . . ? O2 C1 O1 123.0(4) . . ? O2 C1 C2 119.0(3) . . ? O1 C1 C2 118.0(4) . . ? C7 C2 C3 120.0(3) . . ? C7 C2 C1 122.0(3) . . ? C3 C2 C1 118.0(3) . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 C8 119.5(3) . . ? C5 C4 C8 120.5(3) . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? O5 C6 C5 123.8(3) . . ? O5 C6 C7 116.6(3) . . ? C5 C6 C7 119.5(4) . . ? C2 C7 C6 120.0(3) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? O3 C8 O4 122.4(3) . . ? O3 C8 C4 120.6(3) . . ? O4 C8 C4 116.9(3) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 N1 114.1(4) . . ? N5 C10 H10 122.9 . . ? N1 C10 H10 122.9 . . ? N2 C11 N1 110.4(4) . . ? N2 C11 H11 124.8 . . ? N1 C11 H11 124.8 . . ? N2 C12 C14 113.4(3) . . ? N2 C12 H12A 108.9 . . ? C14 C12 H12A 108.9 . . ? N2 C12 H12B 108.9 . . ? C14 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C15 120.8(4) . 2_757 ? C14 C13 H13 119.6 . . ? C15 C13 H13 119.6 2_757 . ? C15 C14 C13 118.6(4) . . ? C15 C14 C12 119.1(4) . . ? C13 C14 C12 122.2(4) . . ? C14 C15 C13 120.6(4) . 2_757 ? C14 C15 H15 119.7 . . ? C13 C15 H15 119.7 2_757 . ? N6 C16 N3 113.8(4) . . ? N6 C16 H16 123.1 . . ? N3 C16 H16 123.1 . . ? N4 C17 N3 110.1(3) . . ? N4 C17 H17 125.0 . . ? N3 C17 H17 125.0 . . ? N4 C18 C20 112.9(4) . . ? N4 C18 H18A 109.0 . . ? C20 C18 H18A 109.0 . . ? N4 C18 H18B 109.0 . . ? C20 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C21 120.0(4) . 2_675 ? C20 C19 H19 120.0 . . ? C21 C19 H19 120.0 2_675 . ? C21 C20 C19 118.8(4) . . ? C21 C20 C18 120.8(4) . . ? C19 C20 C18 120.3(4) . . ? C20 C21 C19 121.2(4) . 2_675 ? C20 C21 H21 119.4 . . ? C19 C21 H21 119.4 2_675 . ? 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 O4 Zn1 O1 C1 166.0(3) 1_455 . . . ? N1 Zn1 O1 C1 51.9(3) . . . . ? N3 Zn1 O1 C1 -78.9(3) . . . . ? O1 Zn1 N1 C11 -19.0(4) . . . . ? O4 Zn1 N1 C11 -126.5(3) 1_455 . . . ? N3 Zn1 N1 C11 99.7(4) . . . . ? O1 Zn1 N1 C10 157.8(3) . . . . ? O4 Zn1 N1 C10 50.2(4) 1_455 . . . ? N3 Zn1 N1 C10 -83.6(4) . . . . ? O1 Zn1 N3 C17 -25.1(3) . . . . ? O4 Zn1 N3 C17 76.0(3) 1_455 . . . ? N1 Zn1 N3 C17 -152.6(3) . . . . ? O1 Zn1 N3 C16 155.1(4) . . . . ? O4 Zn1 N3 C16 -103.7(4) 1_455 . . . ? N1 Zn1 N3 C16 27.7(4) . . . . ? C11 N2 N5 C10 0.5(5) . . . . ? C12 N2 N5 C10 -177.5(4) . . . . ? C17 N4 N6 C16 0.6(5) . . . . ? C18 N4 N6 C16 179.1(4) . . . . ? Zn1 O1 C1 O2 -6.4(5) . . . . ? Zn1 O1 C1 C2 172.9(3) . . . . ? O2 C1 C2 C7 -166.9(4) . . . . ? O1 C1 C2 C7 13.8(6) . . . . ? O2 C1 C2 C3 13.8(6) . . . . ? O1 C1 C2 C3 -165.5(3) . . . . ? C7 C2 C3 C4 0.5(6) . . . . ? C1 C2 C3 C4 179.8(3) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? C2 C3 C4 C8 -179.7(3) . . . . ? C3 C4 C5 C6 -1.1(6) . . . . ? C8 C4 C5 C6 179.4(3) . . . . ? C9 O5 C6 C5 1.8(6) . . . . ? C9 O5 C6 C7 -178.2(4) . . . . ? C4 C5 C6 O5 -179.8(3) . . . . ? C4 C5 C6 C7 0.2(6) . . . . ? C3 C2 C7 C6 -1.3(6) . . . . ? C1 C2 C7 C6 179.4(3) . . . . ? O5 C6 C7 C2 -179.0(3) . . . . ? C5 C6 C7 C2 1.0(6) . . . . ? Zn1 O4 C8 O3 -0.7(4) 1_655 . . . ? Zn1 O4 C8 C4 177.8(2) 1_655 . . . ? C3 C4 C8 O3 14.3(5) . . . . ? C5 C4 C8 O3 -166.1(4) . . . . ? C3 C4 C8 O4 -164.1(3) . . . . ? C5 C4 C8 O4 15.4(5) . . . . ? N2 N5 C10 N1 -0.5(5) . . . . ? C11 N1 C10 N5 0.2(5) . . . . ? Zn1 N1 C10 N5 -177.2(3) . . . . ? N5 N2 C11 N1 -0.4(5) . . . . ? C12 N2 C11 N1 177.4(4) . . . . ? C10 N1 C11 N2 0.1(4) . . . . ? Zn1 N1 C11 N2 177.5(3) . . . . ? C11 N2 C12 C14 -93.4(5) . . . . ? N5 N2 C12 C14 84.2(5) . . . . ? C15 C13 C14 C15 0.7(7) 2_757 . . . ? C15 C13 C14 C12 -176.1(4) 2_757 . . . ? N2 C12 C14 C15 139.0(4) . . . . ? N2 C12 C14 C13 -44.1(5) . . . . ? C13 C14 C15 C13 -0.7(7) . . . 2_757 ? C12 C14 C15 C13 176.2(4) . . . 2_757 ? N4 N6 C16 N3 -0.7(5) . . . . ? C17 N3 C16 N6 0.6(5) . . . . ? Zn1 N3 C16 N6 -179.7(3) . . . . ? N6 N4 C17 N3 -0.3(5) . . . . ? C18 N4 C17 N3 -178.6(4) . . . . ? C16 N3 C17 N4 -0.2(4) . . . . ? Zn1 N3 C17 N4 -179.9(2) . . . . ? C17 N4 C18 C20 -106.1(5) . . . . ? N6 N4 C18 C20 75.8(6) . . . . ? C21 C19 C20 C21 -0.8(8) 2_675 . . . ? C21 C19 C20 C18 -177.2(4) 2_675 . . . ? N4 C18 C20 C21 80.1(6) . . . . ? N4 C18 C20 C19 -103.6(5) . . . . ? C19 C20 C21 C19 0.9(8) . . . 2_675 ? C18 C20 C21 C19 177.2(4) . . . 2_675 ? 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 O6 H2W O6 0.85 2.34 3.052(18) 142.3 2_567 O6 H1W O2 0.85 2.43 2.907(7) 116.0 1_455 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.063 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.084 # Attachment 'x6641.cif' data_x6641 _database_code_depnum_ccdc_archive 'CCDC 849778' #TrackingRef 'x6641.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 N8 O10 Zn2' _chemical_formula_weight 995.60 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.203(5) _cell_length_b 14.382(8) _cell_length_c 14.783(8) _cell_angle_alpha 89.622(7) _cell_angle_beta 77.435(7) _cell_angle_gamma 87.157(7) _cell_volume 2114.7(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1546 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8041 _exptl_absorpt_correction_T_max 0.8747 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15171 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.1591 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7569 _reflns_number_gt 3864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1374P)^2^+4.0384P] 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 7569 _refine_ls_number_parameters 597 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1845 _refine_ls_R_factor_gt 0.1035 _refine_ls_wR_factor_ref 0.2821 _refine_ls_wR_factor_gt 0.2352 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 0.26318(11) -0.16306(8) 1.03644(8) 0.0344(4) Uani 1 1 d . . . Zn2 Zn 0.21987(11) 0.67176(8) 0.54330(8) 0.0318(4) Uani 1 1 d . . . O1 O 0.4785(7) 0.6230(5) 0.5607(6) 0.053(2) Uani 1 1 d . . . O2 O 0.3579(6) 0.7540(4) 0.5665(5) 0.0340(16) Uani 1 1 d . . . O3 O 0.9811(7) 0.6273(5) 0.5106(6) 0.046(2) Uani 1 1 d . . . O4 O 1.0616(6) 0.7589(5) 0.5462(5) 0.0409(18) Uani 1 1 d . . . O5 O 0.6900(8) 0.9991(5) 0.5070(7) 0.062(2) Uani 1 1 d . . . O6 O 0.0044(7) -0.1198(5) 1.0202(5) 0.0437(19) Uani 1 1 d . . . O7 O 0.1150(7) -0.2495(5) 1.0438(5) 0.0431(18) Uani 1 1 d . . . O8 O -0.4851(8) -0.1218(5) 1.0392(6) 0.057(2) Uani 1 1 d . . . O9 O -0.5881(7) -0.2533(5) 1.0543(5) 0.0396(17) Uani 1 1 d . . . O10 O -0.1884(8) -0.4948(5) 0.9958(6) 0.055(2) Uani 1 1 d . . . N1 N 0.1776(8) 0.5749(5) 0.6395(6) 0.035(2) Uani 1 1 d . . . N2 N 0.0980(9) 0.4525(6) 0.7162(7) 0.049(2) Uani 1 1 d . . . N3 N 0.3589(9) -0.0388(6) 0.7778(6) 0.043(2) Uani 1 1 d . . . N4 N 0.2997(8) -0.1196(6) 0.9049(6) 0.037(2) Uani 1 1 d . . . N5 N 0.2937(8) 0.6308(6) 0.4129(6) 0.034(2) Uani 1 1 d . . . N6 N 0.3964(8) 0.5501(6) 0.2903(6) 0.041(2) Uani 1 1 d . . . N7 N 0.1649(9) 0.0758(6) 0.1948(6) 0.042(2) Uani 1 1 d . . . N8 N 0.2167(8) -0.0623(6) 0.1322(6) 0.039(2) Uani 1 1 d . . . C1 C 0.4710(9) 0.7083(7) 0.5591(7) 0.031(2) Uani 1 1 d . . . C2 C 0.5941(9) 0.7610(7) 0.5483(6) 0.028(2) Uani 1 1 d . . . C3 C 0.7165(9) 0.7153(7) 0.5442(6) 0.030(2) Uani 1 1 d . . . H3 H 0.7199 0.6509 0.5507 0.036 Uiso 1 1 calc R . . C4 C 0.8354(9) 0.7616(6) 0.5308(6) 0.028(2) Uani 1 1 d . . . C5 C 0.8276(10) 0.8586(7) 0.5195(7) 0.033(2) Uani 1 1 d . . . H5 H 0.9054 0.8916 0.5109 0.040 Uiso 1 1 calc R . . C6 C 0.7064(10) 0.9052(7) 0.5208(7) 0.034(2) Uani 1 1 d . . . C7 C 0.5899(9) 0.8567(7) 0.5346(7) 0.032(2) Uani 1 1 d . . . H7 H 0.5082 0.8885 0.5347 0.038 Uiso 1 1 calc R . . C8 C 0.9657(9) 0.7117(7) 0.5300(7) 0.031(2) Uani 1 1 d . . . C9 C 0.8060(12) 1.0523(8) 0.4902(10) 0.065(4) Uani 1 1 d . . . H9A H 0.8372 1.0582 0.5466 0.098 Uiso 1 1 calc R . . H9B H 0.7842 1.1131 0.4687 0.098 Uiso 1 1 calc R . . H9C H 0.8753 1.0218 0.4440 0.098 Uiso 1 1 calc R . . C10 C 0.0094(11) -0.2012(8) 1.0318(7) 0.040(3) Uani 1 1 d . . . C11 C -0.1124(9) -0.2580(7) 1.0301(6) 0.030(2) Uani 1 1 d . . . C12 C -0.2377(9) -0.2126(7) 1.0401(6) 0.031(2) Uani 1 1 d . . . H12 H -0.2453 -0.1484 1.0487 0.038 Uiso 1 1 calc R . . C13 C -0.3511(10) -0.2593(7) 1.0379(6) 0.033(2) Uani 1 1 d . . . C14 C -0.3390(9) -0.3563(6) 1.0233(6) 0.028(2) Uani 1 1 d . . . H14 H -0.4140 -0.3900 1.0220 0.033 Uiso 1 1 calc R . . C15 C -0.2148(10) -0.3993(7) 1.0111(7) 0.037(2) Uani 1 1 d . . . C16 C -0.0977(10) -0.3531(7) 1.0142(7) 0.032(2) Uani 1 1 d . . . H16 H -0.0143 -0.3849 1.0059 0.039 Uiso 1 1 calc R . . C17 C -0.2926(12) -0.5497(8) 0.9815(9) 0.054(3) Uani 1 1 d . . . H17A H -0.3638 -0.5478 1.0360 0.081 Uiso 1 1 calc R . . H17B H -0.2586 -0.6128 0.9689 0.081 Uiso 1 1 calc R . . H17C H -0.3264 -0.5258 0.9297 0.081 Uiso 1 1 calc R . . C18 C -0.4825(11) -0.2053(8) 1.0458(7) 0.041(3) Uani 1 1 d . . . C19 C 0.2556(11) -0.1615(8) 0.8346(8) 0.046(3) Uani 1 1 d . . . H19 H 0.2070 -0.2150 0.8403 0.055 Uiso 1 1 calc R . . C20 C 0.2938(12) -0.1125(8) 0.7561(8) 0.051(3) Uani 1 1 d . . . H20 H 0.2785 -0.1266 0.6980 0.061 Uiso 1 1 calc R . . C21 C 0.3614(10) -0.0440(8) 0.8671(7) 0.042(3) Uani 1 1 d . . . H21 H 0.4005 -0.0014 0.8989 0.050 Uiso 1 1 calc R . . C22 C 0.4075(14) 0.0380(10) 0.7164(10) 0.072(4) Uani 1 1 d . . . H22A H 0.4273 0.0156 0.6529 0.087 Uiso 1 1 calc R . . H22B H 0.4910 0.0572 0.7300 0.087 Uiso 1 1 calc R . . C23 C 0.3106(12) 0.1223(8) 0.7240(7) 0.041(3) Uani 1 1 d . . . C24 C 0.1746(13) 0.1148(8) 0.7451(8) 0.050(3) Uani 1 1 d . . . H24 H 0.1395 0.0566 0.7585 0.060 Uiso 1 1 calc R . . C25 C 0.0891(13) 0.1914(9) 0.7471(8) 0.053(3) Uani 1 1 d . . . H25 H -0.0033 0.1849 0.7623 0.064 Uiso 1 1 calc R . . C26 C 0.1389(10) 0.2779(7) 0.7267(7) 0.036(2) Uani 1 1 d . . . C27 C 0.2770(12) 0.2839(9) 0.7061(8) 0.049(3) Uani 1 1 d . . . H27 H 0.3125 0.3422 0.6941 0.059 Uiso 1 1 calc R . . C28 C 0.3613(14) 0.2098(10) 0.7026(9) 0.067(4) Uani 1 1 d . . . H28 H 0.4537 0.2164 0.6860 0.080 Uiso 1 1 calc R . . C29 C 0.0351(12) 0.3604(8) 0.7352(10) 0.067(4) Uani 1 1 d . . . H29A H -0.0225 0.3513 0.6921 0.080 Uiso 1 1 calc R . . H29B H -0.0210 0.3614 0.7973 0.080 Uiso 1 1 calc R . . C30 C 0.1472(13) 0.5025(9) 0.7772(9) 0.061(4) Uani 1 1 d . . . H30 H 0.1474 0.4880 0.8385 0.073 Uiso 1 1 calc R . . C31 C 0.1967(10) 0.5793(8) 0.7288(8) 0.044(3) Uani 1 1 d . . . H31 H 0.2372 0.6272 0.7526 0.053 Uiso 1 1 calc R . . C32 C 0.1172(11) 0.4962(8) 0.6367(8) 0.044(3) Uani 1 1 d . . . H32 H 0.0913 0.4744 0.5844 0.053 Uiso 1 1 calc R . . C33 C 0.2830(11) 0.6777(8) 0.3330(8) 0.047(3) Uani 1 1 d . . . H33 H 0.2387 0.7356 0.3319 0.056 Uiso 1 1 calc R . . C34 C 0.3441(12) 0.6299(8) 0.2578(8) 0.047(3) Uani 1 1 d . . . H34 H 0.3500 0.6470 0.1963 0.056 Uiso 1 1 calc R . . C35 C 0.3652(11) 0.5528(8) 0.3843(8) 0.044(3) Uani 1 1 d . . . H35 H 0.3901 0.5069 0.4229 0.053 Uiso 1 1 calc R . . C36 C 0.4632(12) 0.4691(8) 0.2364(8) 0.051(3) Uani 1 1 d . . . H36A H 0.5347 0.4443 0.2648 0.062 Uiso 1 1 calc R . . H36B H 0.5041 0.4894 0.1744 0.062 Uiso 1 1 calc R . . C37 C 0.3693(11) 0.3918(7) 0.2293(7) 0.037(2) Uani 1 1 d . . . C38 C 0.2319(13) 0.4039(8) 0.2500(8) 0.052(3) Uani 1 1 d . . . H38 H 0.1930 0.4622 0.2695 0.063 Uiso 1 1 calc R . . C39 C 0.1511(12) 0.3339(8) 0.2430(8) 0.053(3) Uani 1 1 d . . . H39 H 0.0583 0.3447 0.2577 0.064 Uiso 1 1 calc R . . C40 C 0.2060(10) 0.2452(7) 0.2138(7) 0.037(2) Uani 1 1 d . . . C41 C 0.3437(11) 0.2335(8) 0.1916(8) 0.047(3) Uani 1 1 d . . . H41 H 0.3834 0.1753 0.1724 0.056 Uiso 1 1 calc R . . C42 C 0.4238(11) 0.3065(8) 0.1972(8) 0.049(3) Uani 1 1 d . . . H42 H 0.5167 0.2976 0.1788 0.059 Uiso 1 1 calc R . . C43 C 0.1055(12) 0.1713(8) 0.2102(9) 0.054(3) Uani 1 1 d . . . H43A H 0.0388 0.1730 0.2681 0.064 Uiso 1 1 calc R . . H43B H 0.0592 0.1868 0.1609 0.064 Uiso 1 1 calc R . . C44 C 0.2329(13) 0.0277(9) 0.2516(9) 0.059(3) Uani 1 1 d . . . H44 H 0.2533 0.0492 0.3060 0.071 Uiso 1 1 calc R . . C45 C 0.2650(12) -0.0586(8) 0.2121(8) 0.054(3) Uani 1 1 d . . . H45 H 0.3118 -0.1069 0.2355 0.065 Uiso 1 1 calc R . . C46 C 0.1594(10) 0.0210(7) 0.1234(7) 0.040(3) Uani 1 1 d . . . H46 H 0.1207 0.0389 0.0741 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0317(7) 0.0237(7) 0.0490(8) -0.0046(5) -0.0114(6) -0.0023(5) Zn2 0.0282(7) 0.0217(6) 0.0464(8) -0.0004(5) -0.0092(5) -0.0034(5) O1 0.027(4) 0.026(4) 0.108(7) -0.001(4) -0.023(4) -0.002(3) O2 0.027(4) 0.025(4) 0.053(4) -0.006(3) -0.015(3) 0.001(3) O3 0.034(4) 0.023(4) 0.084(6) -0.013(4) -0.017(4) 0.003(3) O4 0.023(4) 0.023(4) 0.080(5) -0.006(3) -0.017(4) -0.002(3) O5 0.039(5) 0.026(4) 0.127(8) 0.011(4) -0.031(5) -0.006(3) O6 0.040(5) 0.020(4) 0.074(5) 0.000(4) -0.020(4) -0.006(3) O7 0.030(4) 0.028(4) 0.074(5) 0.001(4) -0.015(4) -0.007(3) O8 0.051(5) 0.021(4) 0.104(7) 0.001(4) -0.025(5) -0.011(4) O9 0.031(4) 0.032(4) 0.059(5) -0.002(3) -0.015(3) -0.003(3) O10 0.046(5) 0.023(4) 0.104(7) -0.014(4) -0.037(5) -0.002(3) N1 0.036(5) 0.019(4) 0.053(6) 0.004(4) -0.016(4) -0.011(4) N2 0.043(6) 0.041(6) 0.068(7) 0.021(5) -0.024(5) -0.015(4) N3 0.058(6) 0.024(5) 0.049(6) -0.002(4) -0.011(5) -0.012(4) N4 0.032(5) 0.026(5) 0.051(5) -0.010(4) -0.008(4) -0.002(4) N5 0.022(4) 0.035(5) 0.048(5) 0.000(4) -0.013(4) -0.001(4) N6 0.032(5) 0.042(6) 0.047(6) -0.001(4) -0.001(4) -0.007(4) N7 0.050(6) 0.025(5) 0.051(6) -0.004(4) -0.010(5) 0.005(4) N8 0.039(5) 0.027(5) 0.054(6) -0.001(4) -0.015(4) -0.005(4) C1 0.026(5) 0.031(6) 0.039(6) -0.003(4) -0.013(4) -0.003(4) C2 0.034(6) 0.030(6) 0.023(5) -0.003(4) -0.010(4) -0.003(4) C3 0.027(5) 0.033(6) 0.029(5) 0.002(4) -0.004(4) -0.008(4) C4 0.033(6) 0.022(5) 0.027(5) -0.003(4) -0.007(4) 0.009(4) C5 0.033(6) 0.026(6) 0.044(6) 0.002(4) -0.014(5) -0.008(4) C6 0.034(6) 0.036(6) 0.034(6) 0.006(5) -0.016(5) -0.005(5) C7 0.022(5) 0.029(6) 0.045(6) -0.003(4) -0.011(4) -0.002(4) C8 0.019(5) 0.038(6) 0.038(6) 0.001(5) -0.009(4) 0.008(4) C9 0.044(7) 0.027(6) 0.134(13) 0.028(7) -0.035(8) -0.023(5) C10 0.034(6) 0.047(8) 0.041(6) 0.008(5) -0.012(5) -0.013(5) C11 0.028(6) 0.031(6) 0.033(6) -0.001(4) -0.012(4) 0.003(4) C12 0.025(5) 0.030(6) 0.040(6) -0.011(4) -0.008(4) 0.000(4) C13 0.045(7) 0.027(6) 0.026(5) 0.002(4) -0.006(5) -0.007(5) C14 0.032(6) 0.015(5) 0.039(6) 0.004(4) -0.011(4) -0.007(4) C15 0.039(6) 0.036(6) 0.038(6) 0.001(5) -0.013(5) 0.002(5) C16 0.034(6) 0.022(5) 0.043(6) 0.004(4) -0.016(5) -0.003(4) C17 0.058(8) 0.035(7) 0.077(9) -0.003(6) -0.034(7) -0.002(6) C18 0.039(7) 0.045(7) 0.039(6) -0.008(5) -0.006(5) -0.015(5) C19 0.042(7) 0.042(7) 0.056(8) -0.006(6) -0.016(6) -0.004(5) C20 0.061(8) 0.044(7) 0.047(7) -0.011(6) -0.012(6) 0.003(6) C21 0.032(6) 0.049(7) 0.047(7) -0.017(5) -0.012(5) -0.007(5) C22 0.080(10) 0.064(10) 0.065(9) 0.015(7) 0.002(7) -0.006(8) C23 0.047(7) 0.037(7) 0.038(6) -0.001(5) -0.008(5) -0.008(5) C24 0.071(9) 0.023(6) 0.056(8) 0.002(5) -0.008(6) -0.010(6) C25 0.053(8) 0.065(9) 0.043(7) 0.008(6) -0.012(6) -0.026(7) C26 0.031(6) 0.037(6) 0.043(6) 0.008(5) -0.010(5) -0.011(5) C27 0.046(7) 0.045(7) 0.054(7) 0.017(6) -0.005(6) -0.017(6) C28 0.059(9) 0.073(10) 0.067(9) 0.025(7) -0.012(7) -0.001(8) C29 0.054(8) 0.042(8) 0.107(11) 0.037(7) -0.019(7) -0.021(6) C30 0.077(10) 0.055(9) 0.061(8) 0.014(7) -0.036(7) -0.015(7) C31 0.032(6) 0.042(7) 0.063(8) 0.001(6) -0.024(5) -0.001(5) C32 0.040(7) 0.035(6) 0.054(7) 0.001(5) -0.004(5) -0.002(5) C33 0.044(7) 0.036(7) 0.061(8) 0.000(6) -0.012(6) -0.001(5) C34 0.058(8) 0.043(7) 0.039(7) 0.007(5) -0.008(6) -0.007(6) C35 0.046(7) 0.038(7) 0.049(7) 0.007(5) -0.011(5) 0.001(5) C36 0.052(8) 0.041(7) 0.055(7) -0.017(6) 0.002(6) -0.002(6) C37 0.045(7) 0.026(6) 0.037(6) 0.000(4) -0.004(5) 0.005(5) C38 0.063(9) 0.019(6) 0.070(8) -0.008(5) -0.009(7) 0.011(5) C39 0.044(7) 0.048(8) 0.066(8) 0.002(6) -0.008(6) 0.006(6) C40 0.036(6) 0.032(6) 0.041(6) -0.007(5) -0.007(5) 0.002(5) C41 0.046(7) 0.030(6) 0.060(8) -0.012(5) -0.001(6) 0.008(5) C42 0.029(6) 0.045(7) 0.074(8) -0.020(6) -0.011(6) 0.003(5) C43 0.049(8) 0.041(7) 0.070(8) -0.013(6) -0.014(6) 0.008(6) C44 0.080(10) 0.051(8) 0.054(8) -0.008(6) -0.031(7) 0.009(7) C45 0.070(9) 0.048(8) 0.057(8) 0.003(6) -0.040(7) 0.004(6) C46 0.041(7) 0.035(6) 0.047(7) -0.003(5) -0.014(5) -0.004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O7 1.989(7) . ? Zn1 N4 2.001(9) . ? Zn1 N8 1.998(8) 1_556 ? Zn1 O9 2.007(7) 1_655 ? Zn2 O2 1.970(6) . ? Zn2 N1 1.979(8) . ? Zn2 O4 1.988(7) 1_455 ? Zn2 N5 1.993(8) . ? O1 C1 1.227(11) . ? O2 C1 1.282(11) . ? O3 C8 1.244(11) . ? O4 C8 1.282(11) . ? O4 Zn2 1.987(7) 1_655 ? O5 C6 1.373(12) . ? O5 C9 1.417(12) . ? O6 C10 1.183(12) . ? O7 C10 1.297(12) . ? O8 C18 1.204(13) . ? O9 C18 1.291(11) . ? O9 Zn1 2.007(7) 1_455 ? O10 C15 1.396(12) . ? O10 C17 1.408(12) . ? N1 C32 1.320(13) . ? N1 C31 1.379(13) . ? N2 C32 1.310(13) . ? N2 C30 1.351(14) . ? N2 C29 1.499(14) . ? N3 C21 1.328(13) . ? N3 C20 1.354(14) . ? N3 C22 1.462(15) . ? N4 C21 1.340(13) . ? N4 C19 1.372(13) . ? N5 C35 1.327(13) . ? N5 C33 1.378(13) . ? N6 C35 1.357(13) . ? N6 C34 1.370(14) . ? N6 C36 1.467(13) . ? N7 C46 1.334(13) . ? N7 C44 1.365(14) . ? N7 C43 1.472(13) . ? N8 C46 1.326(13) . ? N8 C45 1.379(13) . ? N8 Zn1 1.998(8) 1_554 ? C1 C2 1.477(13) . ? C2 C3 1.372(12) . ? C2 C7 1.390(13) . ? C3 C4 1.389(13) . ? C3 H3 0.9300 . ? C4 C5 1.404(13) . ? C4 C8 1.476(12) . ? C5 C6 1.373(13) . ? C5 H5 0.9300 . ? C6 C7 1.384(13) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.525(13) . ? C11 C12 1.385(12) . ? C11 C16 1.385(13) . ? C12 C13 1.373(13) . ? C12 H12 0.9300 . ? C13 C14 1.408(13) . ? C13 C18 1.498(14) . ? C14 C15 1.358(13) . ? C14 H14 0.9300 . ? C15 C16 1.405(13) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 C20 1.348(16) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.515(16) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.364(15) . ? C23 C28 1.392(17) . ? C24 C25 1.367(16) . ? C24 H24 0.9300 . ? C25 C26 1.373(15) . ? C25 H25 0.9300 . ? C26 C27 1.383(14) . ? C26 C29 1.538(15) . ? C27 C28 1.330(16) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.368(16) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C34 1.327(15) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C37 1.522(15) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.370(15) . ? C37 C42 1.366(14) . ? C38 C39 1.351(16) . ? C38 H38 0.9300 . ? C39 C40 1.398(15) . ? C39 H39 0.9300 . ? C40 C41 1.374(14) . ? C40 C43 1.523(15) . ? C41 C42 1.376(15) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.370(16) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? 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 N4 103.9(3) . . ? O7 Zn1 N8 112.1(3) . 1_556 ? N4 Zn1 N8 115.3(3) . 1_556 ? O7 Zn1 O9 100.1(3) . 1_655 ? N4 Zn1 O9 109.5(3) . 1_655 ? N8 Zn1 O9 114.4(3) 1_556 1_655 ? O2 Zn2 N1 112.3(3) . . ? O2 Zn2 O4 103.1(3) . 1_455 ? N1 Zn2 O4 110.8(3) . 1_455 ? O2 Zn2 N5 102.4(3) . . ? N1 Zn2 N5 118.1(3) . . ? O4 Zn2 N5 108.8(3) 1_455 . ? C1 O2 Zn2 110.5(6) . . ? C8 O4 Zn2 108.0(6) . 1_655 ? C6 O5 C9 118.0(8) . . ? C10 O7 Zn1 107.9(6) . . ? C18 O9 Zn1 106.0(7) . 1_455 ? C15 O10 C17 118.9(8) . . ? C32 N1 C31 104.3(9) . . ? C32 N1 Zn2 129.3(8) . . ? C31 N1 Zn2 126.3(7) . . ? C32 N2 C30 109.1(10) . . ? C32 N2 C29 125.3(10) . . ? C30 N2 C29 125.6(10) . . ? C21 N3 C20 108.2(9) . . ? C21 N3 C22 125.2(10) . . ? C20 N3 C22 126.3(11) . . ? C21 N4 C19 105.6(9) . . ? C21 N4 Zn1 129.7(7) . . ? C19 N4 Zn1 124.6(7) . . ? C35 N5 C33 105.2(9) . . ? C35 N5 Zn2 127.3(7) . . ? C33 N5 Zn2 127.5(7) . . ? C35 N6 C34 108.5(9) . . ? C35 N6 C36 123.5(10) . . ? C34 N6 C36 127.7(10) . . ? C46 N7 C44 108.5(9) . . ? C46 N7 C43 125.6(9) . . ? C44 N7 C43 126.0(10) . . ? C46 N8 C45 106.1(9) . . ? C46 N8 Zn1 127.2(7) . 1_554 ? C45 N8 Zn1 125.3(7) . 1_554 ? O1 C1 O2 121.6(9) . . ? O1 C1 C2 120.0(9) . . ? O2 C1 C2 118.4(9) . . ? C3 C2 C7 118.6(9) . . ? C3 C2 C1 120.4(9) . . ? C7 C2 C1 120.8(9) . . ? C2 C3 C4 122.4(9) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C3 C4 C5 117.6(9) . . ? C3 C4 C8 121.8(9) . . ? C5 C4 C8 120.6(9) . . ? C6 C5 C4 120.8(9) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 O5 124.7(9) . . ? C5 C6 C7 120.0(10) . . ? O5 C6 C7 115.2(9) . . ? C6 C7 C2 120.5(9) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? O3 C8 O4 122.1(8) . . ? O3 C8 C4 119.9(9) . . ? O4 C8 C4 117.9(9) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O6 C10 O7 124.8(10) . . ? O6 C10 C11 120.4(10) . . ? O7 C10 C11 114.9(9) . . ? C12 C11 C16 120.0(9) . . ? C12 C11 C10 119.2(9) . . ? C16 C11 C10 120.7(9) . . ? C13 C12 C11 122.2(9) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C12 C13 C14 118.8(9) . . ? C12 C13 C18 119.3(9) . . ? C14 C13 C18 121.8(9) . . ? C15 C14 C13 118.3(9) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C14 C15 O10 124.2(9) . . ? C14 C15 C16 123.9(10) . . ? O10 C15 C16 111.9(8) . . ? C11 C16 C15 116.8(9) . . ? C11 C16 H16 121.6 . . ? C15 C16 H16 121.6 . . ? O10 C17 H17A 109.5 . . ? O10 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O10 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O8 C18 O9 123.2(11) . . ? O8 C18 C13 120.1(10) . . ? O9 C18 C13 116.6(10) . . ? C20 C19 N4 109.1(10) . . ? C20 C19 H19 125.5 . . ? N4 C19 H19 125.5 . . ? C19 C20 N3 106.8(10) . . ? C19 C20 H20 126.6 . . ? N3 C20 H20 126.6 . . ? N3 C21 N4 110.2(9) . . ? N3 C21 H21 124.9 . . ? N4 C21 H21 124.9 . . ? N3 C22 C23 114.7(11) . . ? N3 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? N3 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C28 118.6(11) . . ? C24 C23 C22 122.2(11) . . ? C28 C23 C22 119.1(11) . . ? C25 C24 C23 121.1(11) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 120.4(11) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C27 117.5(11) . . ? C25 C26 C29 116.6(10) . . ? C27 C26 C29 125.8(10) . . ? C28 C27 C26 122.7(12) . . ? C28 C27 H27 118.7 . . ? C26 C27 H27 118.7 . . ? C27 C28 C23 119.7(13) . . ? C27 C28 H28 120.2 . . ? C23 C28 H28 120.2 . . ? N2 C29 C26 113.2(9) . . ? N2 C29 H29A 108.9 . . ? C26 C29 H29A 108.9 . . ? N2 C29 H29B 108.9 . . ? C26 C29 H29B 108.9 . . ? H29A C29 H29B 107.8 . . ? N2 C30 C31 104.8(10) . . ? N2 C30 H30 127.6 . . ? C31 C30 H30 127.6 . . ? C30 C31 N1 109.8(10) . . ? C30 C31 H31 125.1 . . ? N1 C31 H31 125.1 . . ? N2 C32 N1 112.0(10) . . ? N2 C32 H32 124.0 . . ? N1 C32 H32 124.0 . . ? C34 C33 N5 111.6(10) . . ? C34 C33 H33 124.2 . . ? N5 C33 H33 124.2 . . ? C33 C34 N6 105.2(10) . . ? C33 C34 H34 127.4 . . ? N6 C34 H34 127.4 . . ? N5 C35 N6 109.6(9) . . ? N5 C35 H35 125.2 . . ? N6 C35 H35 125.2 . . ? N6 C36 C37 113.8(9) . . ? N6 C36 H36A 108.8 . . ? C37 C36 H36A 108.8 . . ? N6 C36 H36B 108.8 . . ? C37 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C38 C37 C42 117.6(10) . . ? C38 C37 C36 123.6(9) . . ? C42 C37 C36 118.7(10) . . ? C39 C38 C37 122.2(10) . . ? C39 C38 H38 118.9 . . ? C37 C38 H38 118.9 . . ? C38 C39 C40 120.5(11) . . ? C38 C39 H39 119.7 . . ? C40 C39 H39 119.7 . . ? C41 C40 C39 117.3(10) . . ? C41 C40 C43 126.7(10) . . ? C39 C40 C43 116.0(10) . . ? C40 C41 C42 121.0(10) . . ? C40 C41 H41 119.5 . . ? C42 C41 H41 119.5 . . ? C37 C42 C41 121.2(10) . . ? C37 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? N7 C43 C40 114.7(9) . . ? N7 C43 H43A 108.6 . . ? C40 C43 H43A 108.6 . . ? N7 C43 H43B 108.6 . . ? C40 C43 H43B 108.6 . . ? H43A C43 H43B 107.6 . . ? N7 C44 C45 105.8(10) . . ? N7 C44 H44 127.1 . . ? C45 C44 H44 127.1 . . ? C44 C45 N8 108.9(10) . . ? C44 C45 H45 125.5 . . ? N8 C45 H45 125.5 . . ? N8 C46 N7 110.7(9) . . ? N8 C46 H46 124.6 . . ? N7 C46 H46 124.6 . . ? 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 Zn2 O2 C1 66.0(7) . . . . ? O4 Zn2 O2 C1 -174.7(6) 1_455 . . . ? N5 Zn2 O2 C1 -61.8(7) . . . . ? N4 Zn1 O7 C10 -65.8(7) . . . . ? N8 Zn1 O7 C10 59.4(7) 1_556 . . . ? O9 Zn1 O7 C10 -178.9(6) 1_655 . . . ? O2 Zn2 N1 C32 -162.1(9) . . . . ? O4 Zn2 N1 C32 83.2(10) 1_455 . . . ? N5 Zn2 N1 C32 -43.2(10) . . . . ? O2 Zn2 N1 C31 23.4(9) . . . . ? O4 Zn2 N1 C31 -91.3(8) 1_455 . . . ? N5 Zn2 N1 C31 142.3(8) . . . . ? O7 Zn1 N4 C21 159.9(9) . . . . ? N8 Zn1 N4 C21 36.8(10) 1_556 . . . ? O9 Zn1 N4 C21 -93.8(9) 1_655 . . . ? O7 Zn1 N4 C19 -15.4(9) . . . . ? N8 Zn1 N4 C19 -138.5(8) 1_556 . . . ? O9 Zn1 N4 C19 90.8(8) 1_655 . . . ? O2 Zn2 N5 C35 96.2(9) . . . . ? N1 Zn2 N5 C35 -27.8(10) . . . . ? O4 Zn2 N5 C35 -155.1(8) 1_455 . . . ? O2 Zn2 N5 C33 -82.9(8) . . . . ? N1 Zn2 N5 C33 153.2(8) . . . . ? O4 Zn2 N5 C33 25.8(9) 1_455 . . . ? Zn2 O2 C1 O1 -16.5(12) . . . . ? Zn2 O2 C1 C2 163.4(6) . . . . ? O1 C1 C2 C3 -3.0(14) . . . . ? O2 C1 C2 C3 177.1(8) . . . . ? O1 C1 C2 C7 171.8(10) . . . . ? O2 C1 C2 C7 -8.1(13) . . . . ? C7 C2 C3 C4 2.7(13) . . . . ? C1 C2 C3 C4 177.6(8) . . . . ? C2 C3 C4 C5 -1.2(13) . . . . ? C2 C3 C4 C8 177.8(8) . . . . ? C3 C4 C5 C6 -0.6(14) . . . . ? C8 C4 C5 C6 -179.6(9) . . . . ? C4 C5 C6 O5 -177.6(9) . . . . ? C4 C5 C6 C7 0.8(14) . . . . ? C9 O5 C6 C5 -0.1(16) . . . . ? C9 O5 C6 C7 -178.5(10) . . . . ? C5 C6 C7 C2 0.7(14) . . . . ? O5 C6 C7 C2 179.3(9) . . . . ? C3 C2 C7 C6 -2.5(14) . . . . ? C1 C2 C7 C6 -177.4(9) . . . . ? Zn2 O4 C8 O3 -4.1(12) 1_655 . . . ? Zn2 O4 C8 C4 178.6(7) 1_655 . . . ? C3 C4 C8 O3 23.9(14) . . . . ? C5 C4 C8 O3 -157.2(10) . . . . ? C3 C4 C8 O4 -158.7(9) . . . . ? C5 C4 C8 O4 20.2(13) . . . . ? Zn1 O7 C10 O6 -1.2(13) . . . . ? Zn1 O7 C10 C11 176.8(7) . . . . ? O6 C10 C11 C12 -17.4(15) . . . . ? O7 C10 C11 C12 164.5(9) . . . . ? O6 C10 C11 C16 159.4(10) . . . . ? O7 C10 C11 C16 -18.6(14) . . . . ? C16 C11 C12 C13 2.2(15) . . . . ? C10 C11 C12 C13 179.0(9) . . . . ? C11 C12 C13 C14 -1.1(14) . . . . ? C11 C12 C13 C18 -177.8(9) . . . . ? C12 C13 C14 C15 -0.6(14) . . . . ? C18 C13 C14 C15 176.0(9) . . . . ? C13 C14 C15 O10 -179.8(9) . . . . ? C13 C14 C15 C16 1.4(15) . . . . ? C17 O10 C15 C14 7.5(15) . . . . ? C17 O10 C15 C16 -173.6(9) . . . . ? C12 C11 C16 C15 -1.4(14) . . . . ? C10 C11 C16 C15 -178.2(9) . . . . ? C14 C15 C16 C11 -0.4(15) . . . . ? O10 C15 C16 C11 -179.3(9) . . . . ? Zn1 O9 C18 O8 7.4(13) 1_455 . . . ? Zn1 O9 C18 C13 -168.6(7) 1_455 . . . ? C12 C13 C18 O8 11.8(15) . . . . ? C14 C13 C18 O8 -164.8(10) . . . . ? C12 C13 C18 O9 -172.1(9) . . . . ? C14 C13 C18 O9 11.4(14) . . . . ? C21 N4 C19 C20 1.5(12) . . . . ? Zn1 N4 C19 C20 177.8(7) . . . . ? N4 C19 C20 N3 -1.5(13) . . . . ? C21 N3 C20 C19 0.9(13) . . . . ? C22 N3 C20 C19 -174.0(11) . . . . ? C20 N3 C21 N4 0.1(13) . . . . ? C22 N3 C21 N4 175.1(10) . . . . ? C19 N4 C21 N3 -1.0(12) . . . . ? Zn1 N4 C21 N3 -177.0(7) . . . . ? C21 N3 C22 C23 -80.4(15) . . . . ? C20 N3 C22 C23 93.7(15) . . . . ? N3 C22 C23 C24 -31.9(17) . . . . ? N3 C22 C23 C28 152.6(12) . . . . ? C28 C23 C24 C25 -1.1(17) . . . . ? C22 C23 C24 C25 -176.7(11) . . . . ? C23 C24 C25 C26 0.7(17) . . . . ? C24 C25 C26 C27 -1.1(16) . . . . ? C24 C25 C26 C29 -177.2(11) . . . . ? C25 C26 C27 C28 2.1(17) . . . . ? C29 C26 C27 C28 177.8(12) . . . . ? C26 C27 C28 C23 -2.7(19) . . . . ? C24 C23 C28 C27 2.1(18) . . . . ? C22 C23 C28 C27 177.8(12) . . . . ? C32 N2 C29 C26 96.8(13) . . . . ? C30 N2 C29 C26 -81.3(16) . . . . ? C25 C26 C29 N2 177.3(10) . . . . ? C27 C26 C29 N2 1.5(17) . . . . ? C32 N2 C30 C31 0.2(14) . . . . ? C29 N2 C30 C31 178.5(11) . . . . ? N2 C30 C31 N1 -0.2(14) . . . . ? C32 N1 C31 C30 0.1(13) . . . . ? Zn2 N1 C31 C30 175.8(8) . . . . ? C30 N2 C32 N1 -0.1(14) . . . . ? C29 N2 C32 N1 -178.4(10) . . . . ? C31 N1 C32 N2 0.0(12) . . . . ? Zn2 N1 C32 N2 -175.5(7) . . . . ? C35 N5 C33 C34 0.9(12) . . . . ? Zn2 N5 C33 C34 -179.9(7) . . . . ? N5 C33 C34 N6 -0.5(13) . . . . ? C35 N6 C34 C33 -0.1(12) . . . . ? C36 N6 C34 C33 173.9(10) . . . . ? C33 N5 C35 N6 -0.9(12) . . . . ? Zn2 N5 C35 N6 179.9(6) . . . . ? C34 N6 C35 N5 0.7(12) . . . . ? C36 N6 C35 N5 -173.6(9) . . . . ? C35 N6 C36 C37 79.0(13) . . . . ? C34 N6 C36 C37 -94.2(13) . . . . ? N6 C36 C37 C38 15.6(16) . . . . ? N6 C36 C37 C42 -167.1(10) . . . . ? C42 C37 C38 C39 2.6(18) . . . . ? C36 C37 C38 C39 180.0(11) . . . . ? C37 C38 C39 C40 -0.1(19) . . . . ? C38 C39 C40 C41 -1.0(17) . . . . ? C38 C39 C40 C43 178.9(11) . . . . ? C39 C40 C41 C42 -0.6(17) . . . . ? C43 C40 C41 C42 179.6(12) . . . . ? C38 C37 C42 C41 -4.2(17) . . . . ? C36 C37 C42 C41 178.3(11) . . . . ? C40 C41 C42 C37 3.2(18) . . . . ? C46 N7 C43 C40 -119.8(12) . . . . ? C44 N7 C43 C40 61.3(16) . . . . ? C41 C40 C43 N7 9.8(17) . . . . ? C39 C40 C43 N7 -170.1(10) . . . . ? C46 N7 C44 C45 -1.3(14) . . . . ? C43 N7 C44 C45 177.7(11) . . . . ? N7 C44 C45 N8 0.0(15) . . . . ? C46 N8 C45 C44 1.2(14) . . . . ? Zn1 N8 C45 C44 168.5(8) 1_554 . . . ? C45 N8 C46 N7 -2.1(12) . . . . ? Zn1 N8 C46 N7 -169.1(7) 1_554 . . . ? C44 N7 C46 N8 2.2(13) . . . . ? C43 N7 C46 N8 -176.9(10) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 2.401 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.150