# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Su, Zhong-Min' _publ_contact_author_email zmsu@nenu.edu.cn _publ_section_title ; Molecular tectonics of metal-organic frameworks based on ligand-modulated polynuclear zinc SBUs and aromatic multicarboxylic acid ; loop_ _publ_author_name 'Zhong-Min Su' 'Kui-Zhan Shao' # Attachment '- CIF 1-5-revised.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 771703' #TrackingRef '- CIF 1-5-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16 N3 O9 Zn2' _chemical_formula_weight 609.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2050(4) _cell_length_b 19.5300(7) _cell_length_c 11.4550(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.2180(7) _cell_angle_gamma 90.00 _cell_volume 2429.95(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 126 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6201 _exptl_absorpt_correction_T_max 0.7239 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12186 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4284 _reflns_number_gt 3505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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^)+(0.0301P)^2^+2.7523P] 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 4284 _refine_ls_number_parameters 334 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.132 _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 O5 O 0.2841(3) 0.13853(14) 0.4368(3) 0.0505(7) Uani 1 1 d . . . C19 C 0.3687(4) 0.1243(2) 0.3853(4) 0.0421(9) Uani 1 1 d . . . C16 C 0.4163(3) 0.18387(19) 0.3280(3) 0.0377(9) Uani 1 1 d . . . C17 C 0.5067(4) 0.1750(2) 0.2659(4) 0.0511(11) Uani 1 1 d . . . H17 H 0.5360 0.1314 0.2564 0.061 Uiso 1 1 calc R . . C23 C 1.0252(4) 0.4585(2) 0.4107(4) 0.0456(10) Uani 1 1 d . . . H23 H 1.0424 0.4307 0.3509 0.055 Uiso 1 1 calc R . . C18 C 0.5533(4) 0.2309(2) 0.2181(4) 0.0519(11) Uani 1 1 d . . . H18 H 0.6147 0.2247 0.1773 0.062 Uiso 1 1 calc R . . O1W O 0.8449(3) 0.55611(13) 0.9583(3) 0.0498(7) Uani 1 1 d . . . C15 C 0.3723(4) 0.2493(2) 0.3399(4) 0.0458(10) Uani 1 1 d . . . H15 H 0.3115 0.2557 0.3813 0.055 Uiso 1 1 calc R . . C14 C 0.4183(4) 0.3046(2) 0.2907(4) 0.0473(10) Uani 1 1 d . . . H14 H 0.3875 0.3482 0.2982 0.057 Uiso 1 1 calc R . . C13 C 0.5096(3) 0.29601(18) 0.2302(3) 0.0369(9) Uani 1 1 d . . . Zn1 Zn 0.54965(4) 0.51335(2) 0.14046(4) 0.03008(13) Uani 1 1 d . . . Zn2 Zn 0.72980(4) 0.41383(2) 0.05423(4) 0.02967(13) Uani 1 1 d . . . O2 O 0.6170(2) 0.48909(11) -0.0094(2) 0.0285(5) Uani 1 1 d . . . O8 O 0.8506(2) 0.44938(15) 0.1937(2) 0.0481(7) Uani 1 1 d . . . N1 N 0.5815(3) 0.62965(17) 0.1253(3) 0.0443(8) Uani 1 1 d . . . O3 O 0.5148(3) 0.41412(13) 0.1881(3) 0.0465(7) Uani 1 1 d . . . O7 O 0.7185(2) 0.51357(15) 0.2638(2) 0.0501(7) Uani 1 1 d . . . C21 C 0.9150(3) 0.49426(19) 0.3898(3) 0.0366(9) Uani 1 1 d . . . O4 O 0.6441(3) 0.34471(14) 0.1256(3) 0.0542(8) Uani 1 1 d . . . O6 O 0.4137(3) 0.06670(15) 0.3810(3) 0.0643(9) Uani 1 1 d . . . C22 C 0.8909(4) 0.5357(2) 0.4792(4) 0.0453(10) Uani 1 1 d . . . H22 H 0.8174 0.5600 0.4649 0.054 Uiso 1 1 calc R . . N2 N 0.4580(3) 0.55355(18) 0.2775(3) 0.0460(8) Uani 1 1 d . . . C20 C 0.8206(3) 0.48552(19) 0.2723(3) 0.0371(9) Uani 1 1 d . . . C10 C 0.4655(4) 0.6206(2) 0.2796(4) 0.0470(10) Uani 1 1 d . . . C1 C 0.6384(4) 0.6726(2) 0.0672(5) 0.0641(13) Uani 1 1 d . . . H1 H 0.6793 0.6554 0.0119 0.077 Uiso 1 1 calc R . . C7 C 0.3623(6) 0.6347(4) 0.4346(6) 0.095(2) Uani 1 1 d U . . H7 H 0.3306 0.6610 0.4877 0.115 Uiso 1 1 calc R . . C11 C 0.5269(4) 0.6587(2) 0.2046(4) 0.0485(11) Uani 1 1 d . . . C12 C 0.5601(3) 0.3568(2) 0.1783(3) 0.0386(9) Uani 1 1 d . . . C6 C 0.4196(5) 0.6652(3) 0.3540(5) 0.0659(14) Uani 1 1 d U . . C4 C 0.5197(5) 0.7282(2) 0.2300(5) 0.0654(14) Uani 1 1 d U . . O1 O 0.4338(4) 0.8332(3) 0.3326(4) 0.1173(16) Uani 1 1 d . . . H1O H 0.4172 0.8721 0.3506 0.176 Uiso 1 1 calc R . . N3 N 0.3891(5) 0.7912(3) 0.3903(5) 0.1044(18) Uani 1 1 d U . . C9 C 0.4000(5) 0.5264(3) 0.3556(5) 0.0745(15) Uani 1 1 d U . . H9 H 0.3905 0.4792 0.3568 0.089 Uiso 1 1 calc R . . C3 C 0.5791(6) 0.7713(3) 0.1699(6) 0.0882(18) Uani 1 1 d U . . H3 H 0.5798 0.8182 0.1840 0.106 Uiso 1 1 calc R . . C8 C 0.3536(6) 0.5654(4) 0.4341(6) 0.103(2) Uani 1 1 d U . . H8 H 0.3156 0.5440 0.4879 0.123 Uiso 1 1 calc R . . C2 C 0.6383(6) 0.7445(3) 0.0877(6) 0.0884(18) Uani 1 1 d U . . H2 H 0.6783 0.7736 0.0455 0.106 Uiso 1 1 calc R . . C5 C 0.4487(5) 0.7343(3) 0.3215(5) 0.0748(16) Uani 1 1 d U . . H2O H 0.6591 0.5205 -0.0263 0.112 Uiso 1 1 d R . . H1A H 0.8684 0.5203 0.9281 0.112 Uiso 1 1 d R . . H1B H 0.8979 0.5618 1.0241 0.112 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0509(17) 0.0494(17) 0.0563(18) 0.0188(14) 0.0230(15) -0.0027(14) C19 0.040(2) 0.044(2) 0.042(2) 0.0103(19) 0.0098(19) -0.0031(19) C16 0.041(2) 0.032(2) 0.041(2) 0.0086(17) 0.0121(18) -0.0023(16) C17 0.066(3) 0.031(2) 0.067(3) 0.011(2) 0.036(3) 0.0080(19) C23 0.042(2) 0.053(3) 0.039(2) -0.0097(19) 0.0029(19) 0.0055(19) C18 0.060(3) 0.042(2) 0.066(3) 0.013(2) 0.040(2) 0.007(2) O1W 0.0548(18) 0.0313(14) 0.068(2) 0.0006(14) 0.0243(16) 0.0001(13) C15 0.047(2) 0.042(2) 0.056(3) 0.010(2) 0.028(2) 0.0014(19) C14 0.052(2) 0.035(2) 0.060(3) 0.008(2) 0.026(2) 0.0061(19) C13 0.042(2) 0.032(2) 0.039(2) 0.0076(17) 0.0138(18) -0.0014(16) Zn1 0.0324(2) 0.0292(2) 0.0276(2) -0.00208(17) 0.00531(18) 0.00350(17) Zn2 0.0308(2) 0.0291(2) 0.0304(2) -0.00060(18) 0.00997(18) 0.00209(17) O2 0.0295(12) 0.0275(12) 0.0290(13) 0.0010(10) 0.0082(10) -0.0005(10) O8 0.0392(15) 0.0634(19) 0.0365(15) -0.0145(14) -0.0007(13) 0.0068(14) N1 0.0443(19) 0.0384(19) 0.045(2) -0.0046(16) 0.0011(17) -0.0022(15) O3 0.0555(17) 0.0325(15) 0.0553(18) 0.0087(13) 0.0210(15) -0.0008(13) O7 0.0406(16) 0.0608(18) 0.0404(16) -0.0113(14) -0.0065(13) 0.0122(14) C21 0.034(2) 0.041(2) 0.033(2) -0.0008(17) 0.0034(16) -0.0016(17) O4 0.0580(18) 0.0387(16) 0.077(2) 0.0166(15) 0.0377(17) 0.0025(14) O6 0.073(2) 0.0375(17) 0.092(3) 0.0185(17) 0.040(2) 0.0024(15) C22 0.034(2) 0.053(2) 0.042(2) -0.008(2) -0.0039(18) 0.0080(18) N2 0.048(2) 0.048(2) 0.0402(19) -0.0085(16) 0.0083(16) 0.0037(16) C20 0.034(2) 0.038(2) 0.034(2) -0.0001(18) 0.0000(17) -0.0019(17) C10 0.041(2) 0.050(3) 0.047(2) -0.017(2) 0.003(2) 0.0080(19) C1 0.061(3) 0.058(3) 0.068(3) 0.002(3) 0.005(3) -0.014(2) C7 0.090(3) 0.121(4) 0.086(3) -0.034(3) 0.042(3) 0.016(3) C11 0.043(2) 0.040(2) 0.052(3) -0.016(2) -0.008(2) 0.0097(19) C12 0.038(2) 0.038(2) 0.039(2) 0.0098(18) 0.0081(18) -0.0035(17) C6 0.060(3) 0.067(3) 0.065(3) -0.029(2) 0.005(2) 0.016(2) C4 0.063(3) 0.043(2) 0.078(3) -0.012(2) -0.007(2) 0.003(2) O1 0.098(3) 0.154(5) 0.099(3) 0.008(3) 0.021(3) -0.019(3) N3 0.093(3) 0.121(4) 0.085(3) 0.034(3) -0.005(3) -0.046(3) C9 0.083(3) 0.082(3) 0.068(3) -0.007(3) 0.037(3) -0.002(3) C3 0.093(4) 0.059(3) 0.101(4) -0.011(3) 0.002(3) 0.000(3) C8 0.104(4) 0.124(4) 0.095(4) -0.016(3) 0.054(3) -0.005(3) C2 0.087(3) 0.071(3) 0.099(4) 0.019(3) 0.007(3) -0.031(3) C5 0.065(3) 0.068(3) 0.081(3) -0.041(3) -0.001(3) 0.027(2) _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 O5 C19 1.264(5) . ? O5 Zn2 1.905(3) 4_566 ? C19 O6 1.239(5) . ? C19 C16 1.496(5) . ? C16 C17 1.384(5) . ? C16 C15 1.388(5) . ? C17 C18 1.380(5) . ? C17 H17 0.9300 . ? C23 C22 1.381(5) 3_766 ? C23 C21 1.387(5) . ? C23 H23 0.9300 . ? C18 C13 1.382(5) . ? C18 H18 0.9300 . ? O1W H1A 0.8494 . ? O1W H1B 0.8450 . ? C15 C14 1.376(5) . ? C15 H15 0.9300 . ? C14 C13 1.380(5) . ? C14 H14 0.9300 . ? C13 C12 1.499(5) . ? Zn1 O7 2.065(3) . ? Zn1 O3 2.076(3) . ? Zn1 O2 2.090(2) 3_665 ? Zn1 O2 2.092(2) . ? Zn1 N2 2.220(3) . ? Zn1 N1 2.312(3) . ? Zn1 Zn2 3.1317(6) . ? Zn2 O5 1.905(3) 4_665 ? Zn2 O4 1.949(3) . ? Zn2 O8 1.950(3) . ? Zn2 O2 1.959(2) . ? O2 Zn1 2.090(2) 3_665 ? O2 H2O 0.8249 . ? O8 C20 1.254(4) . ? N1 C1 1.328(6) . ? N1 C11 1.339(5) . ? O3 C12 1.246(4) . ? O7 C20 1.250(4) . ? C21 C22 1.383(5) . ? C21 C20 1.503(5) . ? O4 C12 1.259(5) . ? C22 C23 1.381(5) 3_766 ? C22 H22 0.9300 . ? N2 C10 1.312(5) . ? N2 C9 1.337(6) . ? C10 C6 1.402(6) . ? C10 C11 1.434(6) . ? C1 C2 1.424(7) . ? C1 H1 0.9300 . ? C7 C8 1.357(9) . ? C7 C6 1.382(8) . ? C7 H7 0.9300 . ? C11 C4 1.394(6) . ? C6 C5 1.457(8) . ? C4 C3 1.359(8) . ? C4 C5 1.468(8) . ? O1 N3 1.235(6) . ? O1 H1O 0.8200 . ? N3 C5 1.600(8) . ? C9 C8 1.374(8) . ? C9 H9 0.9300 . ? C3 C2 1.381(8) . ? C3 H3 0.9300 . ? C8 H8 0.9300 . ? C2 H2 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 C19 O5 Zn2 128.2(3) . 4_566 ? O6 C19 O5 125.2(4) . . ? O6 C19 C16 119.7(4) . . ? O5 C19 C16 115.0(4) . . ? C17 C16 C15 119.2(3) . . ? C17 C16 C19 120.9(4) . . ? C15 C16 C19 119.9(4) . . ? C18 C17 C16 120.1(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C22 C23 C21 119.6(4) 3_766 . ? C22 C23 H23 120.2 3_766 . ? C21 C23 H23 120.2 . . ? C17 C18 C13 120.7(4) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? H1A O1W H1B 104.6 . . ? C14 C15 C16 120.4(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C13 C18 119.2(4) . . ? C14 C13 C12 120.1(3) . . ? C18 C13 C12 120.8(3) . . ? O7 Zn1 O3 91.26(12) . . ? O7 Zn1 O2 177.12(10) . 3_665 ? O3 Zn1 O2 88.57(10) . 3_665 ? O7 Zn1 O2 96.15(10) . . ? O3 Zn1 O2 97.65(10) . . ? O2 Zn1 O2 81.02(9) 3_665 . ? O7 Zn1 N2 91.20(12) . . ? O3 Zn1 N2 89.70(12) . . ? O2 Zn1 N2 91.68(11) 3_665 . ? O2 Zn1 N2 169.46(11) . . ? O7 Zn1 N1 85.24(11) . . ? O3 Zn1 N1 168.25(12) . . ? O2 Zn1 N1 95.48(10) 3_665 . ? O2 Zn1 N1 93.87(11) . . ? N2 Zn1 N1 79.18(13) . . ? O7 Zn1 Zn2 70.35(8) . . ? O3 Zn1 Zn2 71.39(8) . . ? O2 Zn1 Zn2 106.89(6) 3_665 . ? O2 Zn1 Zn2 37.84(6) . . ? N2 Zn1 Zn2 152.69(9) . . ? N1 Zn1 Zn2 117.56(9) . . ? O5 Zn2 O4 101.55(13) 4_665 . ? O5 Zn2 O8 119.45(12) 4_665 . ? O4 Zn2 O8 102.55(13) . . ? O5 Zn2 O2 115.42(11) 4_665 . ? O4 Zn2 O2 109.66(11) . . ? O8 Zn2 O2 106.99(11) . . ? O5 Zn2 Zn1 153.97(9) 4_665 . ? O4 Zn2 Zn1 82.85(8) . . ? O8 Zn2 Zn1 83.81(8) . . ? O2 Zn2 Zn1 40.93(7) . . ? Zn2 O2 Zn1 129.14(11) . 3_665 ? Zn2 O2 Zn1 101.23(10) . . ? Zn1 O2 Zn1 98.98(9) 3_665 . ? Zn2 O2 H2O 106.9 . . ? Zn1 O2 H2O 108.0 3_665 . ? Zn1 O2 H2O 111.5 . . ? C20 O8 Zn2 122.3(2) . . ? C1 N1 C11 115.4(4) . . ? C1 N1 Zn1 139.5(3) . . ? C11 N1 Zn1 105.1(3) . . ? C12 O3 Zn1 135.1(3) . . ? C20 O7 Zn1 136.0(3) . . ? C22 C21 C23 119.6(4) . . ? C22 C21 C20 120.4(3) . . ? C23 C21 C20 119.9(4) . . ? C12 O4 Zn2 125.1(3) . . ? C23 C22 C21 120.8(4) 3_766 . ? C23 C22 H22 119.6 3_766 . ? C21 C22 H22 119.6 . . ? C10 N2 C9 115.0(4) . . ? C10 N2 Zn1 109.1(3) . . ? C9 N2 Zn1 135.9(3) . . ? O7 C20 O8 126.3(3) . . ? O7 C20 C21 116.7(3) . . ? O8 C20 C21 116.9(3) . . ? N2 C10 C6 126.9(5) . . ? N2 C10 C11 123.0(4) . . ? C6 C10 C11 110.1(4) . . ? N1 C1 C2 121.3(5) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C8 C7 C6 118.2(5) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? N1 C11 C4 127.8(5) . . ? N1 C11 C10 123.5(4) . . ? C4 C11 C10 108.6(4) . . ? O3 C12 O4 125.5(3) . . ? O3 C12 C13 118.3(3) . . ? O4 C12 C13 116.2(3) . . ? C7 C6 C10 116.0(5) . . ? C7 C6 C5 137.7(5) . . ? C10 C6 C5 106.4(5) . . ? C3 C4 C11 115.9(5) . . ? C3 C4 C5 136.9(5) . . ? C11 C4 C5 107.2(5) . . ? N3 O1 H1O 109.5 . . ? O1 N3 C5 85.7(5) . . ? N2 C9 C8 122.8(6) . . ? N2 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C4 C3 C2 119.2(5) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C7 C8 C9 121.1(6) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C3 C2 C1 120.5(6) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C6 C5 C4 107.6(4) . . ? C6 C5 N3 111.7(5) . . ? C4 C5 N3 140.6(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 Zn2 O5 C19 O6 17.6(6) 4_566 . . . ? Zn2 O5 C19 C16 -161.5(3) 4_566 . . . ? O6 C19 C16 C17 2.6(6) . . . . ? O5 C19 C16 C17 -178.2(4) . . . . ? O6 C19 C16 C15 -175.5(4) . . . . ? O5 C19 C16 C15 3.6(6) . . . . ? C15 C16 C17 C18 0.9(7) . . . . ? C19 C16 C17 C18 -177.2(4) . . . . ? C16 C17 C18 C13 -0.8(7) . . . . ? C17 C16 C15 C14 -0.2(6) . . . . ? C19 C16 C15 C14 178.0(4) . . . . ? C16 C15 C14 C13 -0.8(7) . . . . ? C15 C14 C13 C18 0.9(6) . . . . ? C15 C14 C13 C12 -179.2(4) . . . . ? C17 C18 C13 C14 -0.1(7) . . . . ? C17 C18 C13 C12 -180.0(4) . . . . ? O7 Zn1 Zn2 O5 -160.0(2) . . . 4_665 ? O3 Zn1 Zn2 O5 101.7(2) . . . 4_665 ? O2 Zn1 Zn2 O5 19.2(2) 3_665 . . 4_665 ? O2 Zn1 Zn2 O5 -29.8(2) . . . 4_665 ? N2 Zn1 Zn2 O5 150.1(3) . . . 4_665 ? N1 Zn1 Zn2 O5 -86.6(2) . . . 4_665 ? O7 Zn1 Zn2 O4 98.35(13) . . . . ? O3 Zn1 Zn2 O4 0.02(13) . . . . ? O2 Zn1 Zn2 O4 -82.53(12) 3_665 . . . ? O2 Zn1 Zn2 O4 -131.47(14) . . . . ? N2 Zn1 Zn2 O4 48.4(2) . . . . ? N1 Zn1 Zn2 O4 171.74(13) . . . . ? O7 Zn1 Zn2 O8 -5.18(13) . . . . ? O3 Zn1 Zn2 O8 -103.50(12) . . . . ? O2 Zn1 Zn2 O8 173.95(11) 3_665 . . . ? O2 Zn1 Zn2 O8 125.01(14) . . . . ? N2 Zn1 Zn2 O8 -55.1(2) . . . . ? N1 Zn1 Zn2 O8 68.22(13) . . . . ? O7 Zn1 Zn2 O2 -130.18(13) . . . . ? O3 Zn1 Zn2 O2 131.49(13) . . . . ? O2 Zn1 Zn2 O2 48.94(15) 3_665 . . . ? N2 Zn1 Zn2 O2 179.9(2) . . . . ? N1 Zn1 Zn2 O2 -56.79(13) . . . . ? O5 Zn2 O2 Zn1 54.52(18) 4_665 . . 3_665 ? O4 Zn2 O2 Zn1 -59.38(18) . . . 3_665 ? O8 Zn2 O2 Zn1 -169.89(14) . . . 3_665 ? Zn1 Zn2 O2 Zn1 -111.52(17) . . . 3_665 ? O5 Zn2 O2 Zn1 166.04(11) 4_665 . . . ? O4 Zn2 O2 Zn1 52.14(14) . . . . ? O8 Zn2 O2 Zn1 -58.37(13) . . . . ? O7 Zn1 O2 Zn2 46.35(12) . . . . ? O3 Zn1 O2 Zn2 -45.75(12) . . . . ? O2 Zn1 O2 Zn2 -133.08(14) 3_665 . . . ? N2 Zn1 O2 Zn2 -179.7(6) . . . . ? N1 Zn1 O2 Zn2 131.98(11) . . . . ? O7 Zn1 O2 Zn1 179.43(11) . . . 3_665 ? O3 Zn1 O2 Zn1 87.33(11) . . . 3_665 ? O2 Zn1 O2 Zn1 0.0 3_665 . . 3_665 ? N2 Zn1 O2 Zn1 -46.6(6) . . . 3_665 ? N1 Zn1 O2 Zn1 -94.95(11) . . . 3_665 ? Zn2 Zn1 O2 Zn1 133.08(14) . . . 3_665 ? O5 Zn2 O8 C20 178.2(3) 4_665 . . . ? O4 Zn2 O8 C20 -70.6(3) . . . . ? O2 Zn2 O8 C20 44.8(3) . . . . ? Zn1 Zn2 O8 C20 10.7(3) . . . . ? O7 Zn1 N1 C1 84.0(4) . . . . ? O3 Zn1 N1 C1 157.0(5) . . . . ? O2 Zn1 N1 C1 -93.2(4) 3_665 . . . ? O2 Zn1 N1 C1 -11.9(4) . . . . ? N2 Zn1 N1 C1 176.1(5) . . . . ? Zn2 Zn1 N1 C1 19.1(5) . . . . ? O7 Zn1 N1 C11 -93.1(3) . . . . ? O3 Zn1 N1 C11 -20.1(7) . . . . ? O2 Zn1 N1 C11 89.7(2) 3_665 . . . ? O2 Zn1 N1 C11 171.1(2) . . . . ? N2 Zn1 N1 C11 -0.9(2) . . . . ? Zn2 Zn1 N1 C11 -158.0(2) . . . . ? O7 Zn1 O3 C12 -66.9(4) . . . . ? O2 Zn1 O3 C12 110.2(4) 3_665 . . . ? O2 Zn1 O3 C12 29.5(4) . . . . ? N2 Zn1 O3 C12 -158.1(4) . . . . ? N1 Zn1 O3 C12 -139.3(5) . . . . ? Zn2 Zn1 O3 C12 1.9(4) . . . . ? O3 Zn1 O7 C20 71.7(4) . . . . ? O2 Zn1 O7 C20 -15(2) 3_665 . . . ? O2 Zn1 O7 C20 -26.2(4) . . . . ? N2 Zn1 O7 C20 161.4(4) . . . . ? N1 Zn1 O7 C20 -119.5(4) . . . . ? Zn2 Zn1 O7 C20 2.0(4) . . . . ? C22 C23 C21 C22 0.5(7) 3_766 . . . ? C22 C23 C21 C20 -177.0(4) 3_766 . . . ? O5 Zn2 O4 C12 -155.6(3) 4_665 . . . ? O8 Zn2 O4 C12 80.4(3) . . . . ? O2 Zn2 O4 C12 -33.1(4) . . . . ? Zn1 Zn2 O4 C12 -1.6(3) . . . . ? C23 C21 C22 C23 -0.5(7) . . . 3_766 ? C20 C21 C22 C23 177.0(4) . . . 3_766 ? O7 Zn1 N2 C10 86.0(3) . . . . ? O3 Zn1 N2 C10 177.3(3) . . . . ? O2 Zn1 N2 C10 -94.1(3) 3_665 . . . ? O2 Zn1 N2 C10 -48.3(7) . . . . ? N1 Zn1 N2 C10 1.1(3) . . . . ? Zn2 Zn1 N2 C10 132.2(2) . . . . ? O7 Zn1 N2 C9 -93.5(5) . . . . ? O3 Zn1 N2 C9 -2.3(5) . . . . ? O2 Zn1 N2 C9 86.3(5) 3_665 . . . ? O2 Zn1 N2 C9 132.2(6) . . . . ? N1 Zn1 N2 C9 -178.5(5) . . . . ? Zn2 Zn1 N2 C9 -47.4(6) . . . . ? Zn1 O7 C20 O8 5.8(7) . . . . ? Zn1 O7 C20 C21 -172.2(3) . . . . ? Zn2 O8 C20 O7 -13.6(6) . . . . ? Zn2 O8 C20 C21 164.4(2) . . . . ? C22 C21 C20 O7 -4.6(6) . . . . ? C23 C21 C20 O7 172.9(4) . . . . ? C22 C21 C20 O8 177.2(4) . . . . ? C23 C21 C20 O8 -5.3(6) . . . . ? C9 N2 C10 C6 0.0(6) . . . . ? Zn1 N2 C10 C6 -179.7(4) . . . . ? C9 N2 C10 C11 178.5(4) . . . . ? Zn1 N2 C10 C11 -1.2(5) . . . . ? C11 N1 C1 C2 -1.1(6) . . . . ? Zn1 N1 C1 C2 -177.9(4) . . . . ? C1 N1 C11 C4 2.2(6) . . . . ? Zn1 N1 C11 C4 -179.9(4) . . . . ? C1 N1 C11 C10 -177.2(4) . . . . ? Zn1 N1 C11 C10 0.7(4) . . . . ? N2 C10 C11 N1 0.4(6) . . . . ? C6 C10 C11 N1 179.1(4) . . . . ? N2 C10 C11 C4 -179.1(4) . . . . ? C6 C10 C11 C4 -0.4(5) . . . . ? Zn1 O3 C12 O4 -3.9(7) . . . . ? Zn1 O3 C12 C13 177.7(3) . . . . ? Zn2 O4 C12 O3 3.5(6) . . . . ? Zn2 O4 C12 C13 -178.0(2) . . . . ? C14 C13 C12 O3 -2.2(6) . . . . ? C18 C13 C12 O3 177.7(4) . . . . ? C14 C13 C12 O4 179.3(4) . . . . ? C18 C13 C12 O4 -0.9(6) . . . . ? C8 C7 C6 C10 -0.9(8) . . . . ? C8 C7 C6 C5 179.4(6) . . . . ? N2 C10 C6 C7 1.1(7) . . . . ? C11 C10 C6 C7 -177.5(4) . . . . ? N2 C10 C6 C5 -179.1(4) . . . . ? C11 C10 C6 C5 2.3(5) . . . . ? N1 C11 C4 C3 -2.5(7) . . . . ? C10 C11 C4 C3 177.0(4) . . . . ? N1 C11 C4 C5 178.9(4) . . . . ? C10 C11 C4 C5 -1.6(5) . . . . ? C10 N2 C9 C8 -1.3(8) . . . . ? Zn1 N2 C9 C8 178.3(4) . . . . ? C11 C4 C3 C2 1.6(8) . . . . ? C5 C4 C3 C2 179.6(6) . . . . ? C6 C7 C8 C9 -0.2(10) . . . . ? N2 C9 C8 C7 1.5(10) . . . . ? C4 C3 C2 C1 -0.7(9) . . . . ? N1 C1 C2 C3 0.5(8) . . . . ? C7 C6 C5 C4 176.5(6) . . . . ? C10 C6 C5 C4 -3.2(5) . . . . ? C7 C6 C5 N3 -6.2(9) . . . . ? C10 C6 C5 N3 174.1(4) . . . . ? C3 C4 C5 C6 -175.2(6) . . . . ? C11 C4 C5 C6 3.0(5) . . . . ? C3 C4 C5 N3 8.8(11) . . . . ? C11 C4 C5 N3 -173.1(5) . . . . ? O1 N3 C5 C6 -177.9(4) . . . . ? O1 N3 C5 C4 -1.9(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O1W 0.82 2.15 2.906(6) 152.6 4_575 O2 H2O O1W 0.82 2.24 2.972(3) 147.6 1_554 O1W H1A O6 0.85 1.89 2.733(4) 171.0 4_666 O1W H1B O6 0.85 2.13 2.882(5) 148.7 2_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.820 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.067 data_2 _database_code_depnum_ccdc_archive 'CCDC 771704' #TrackingRef '- CIF 1-5-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 N3 O12 Zn2' _chemical_formula_weight 648.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.3267(5) _cell_length_b 15.0656(6) _cell_length_c 14.5968(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.6310(10) _cell_angle_gamma 90.00 _cell_volume 2568.70(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 164 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.936 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6866 _exptl_absorpt_correction_T_max 0.8009 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15684 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6136 _reflns_number_gt 4676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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. All absorption corrections were performed by using the SADABS program. The crystal structure was solved by direct methods and refined with full-matrix least-squares (SHELXTL-97) with atomic coordinates and anisotropic thermal parameters for all nonhydrogen atoms. The hydrogen atoms of aromatic rings were included in the structure factor calculation at idealized positions by using a riding model. Some of the water H atoms could not be positioned reliably. N3 and O1 atoms were splited to different positions and C2 to C9 atoms were treated with restained refinement. ; _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^)+(0.0683P)^2^+0.3218P] 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 6136 _refine_ls_number_parameters 380 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.173 _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 O2W O 0.8620(8) 0.3830(6) 0.3651(8) 0.130(3) Uani 0.50 1 d P . . O3W O 0.3499(11) 0.2507(8) 0.6125(10) 0.168(5) Uani 0.50 1 d P . . N3A N 0.3339(11) -0.3580(7) 0.3605(5) 0.068(3) Uani 0.61(2) 1 d P A 1 O1A O 0.2780(6) -0.4365(8) 0.3539(6) 0.088(3) Uani 0.61(2) 1 d P A 1 O1B O 0.3730(11) -0.3902(8) 0.3551(9) 0.088(4) Uani 0.39(2) 1 d P A 2 N3B N 0.2594(10) -0.3906(11) 0.3688(8) 0.063(3) Uani 0.39(2) 1 d P A 2 C3 C 0.0437(6) -0.3555(3) 0.3769(4) 0.0956(17) Uani 1 1 d U . . H3 H 0.0522 -0.4162 0.3696 0.115 Uiso 1 1 calc R . . C5 C 0.2470(5) -0.3026(3) 0.3742(3) 0.0857(15) Uani 1 1 d U . . H2O H -0.1562 -0.0122 0.4151 0.129 Uiso 1 1 d R A . O2 O -0.10158(17) 0.02333(13) 0.43276(16) 0.0378(5) Uani 1 1 d . . . Zn2 Zn -0.14370(3) 0.12493(2) 0.34504(3) 0.04128(13) Uani 1 1 d . . . Zn1 Zn 0.05132(3) -0.02115(2) 0.41745(3) 0.04101(13) Uani 1 1 d . . . O7 O -0.01308(19) 0.20658(17) 0.3598(2) 0.0582(7) Uani 1 1 d . . . O6 O 0.12101(19) 0.10597(16) 0.42424(19) 0.0515(6) Uani 1 1 d . . . C20 C 0.0891(3) 0.1796(2) 0.3893(2) 0.0423(7) Uani 1 1 d . . . C1 C -0.0700(5) -0.2292(3) 0.3954(3) 0.0726(12) Uani 1 1 d . A . H1 H -0.1396 -0.2084 0.3991 0.087 Uiso 1 1 calc R . . C2 C -0.0565(6) -0.3212(4) 0.3833(4) 0.0896(15) Uani 1 1 d U . . H2 H -0.1170 -0.3594 0.3796 0.108 Uiso 1 1 calc R . . C4 C 0.1314(5) -0.2973(3) 0.3816(3) 0.0758(13) Uani 1 1 d U A . C6 C 0.2937(4) -0.2109(3) 0.3822(3) 0.0727(13) Uani 1 1 d U A . C7 C 0.3933(4) -0.1697(4) 0.3809(4) 0.0883(15) Uani 1 1 d U . . H7 H 0.4541 -0.2024 0.3736 0.106 Uiso 1 1 calc R A . C8 C 0.3998(4) -0.0793(4) 0.3908(4) 0.0890(15) Uani 1 1 d U A . H8 H 0.4658 -0.0500 0.3897 0.107 Uiso 1 1 calc R . . C9 C 0.3103(4) -0.0310(3) 0.4024(4) 0.0732(12) Uani 1 1 d U . . H9 H 0.3178 0.0303 0.4090 0.088 Uiso 1 1 calc R A . C10 C 0.2076(3) -0.1560(3) 0.3947(3) 0.0552(9) Uani 1 1 d . . . C11 C 0.1093(4) -0.2069(2) 0.3938(3) 0.0571(10) Uani 1 1 d . A . C12 C 0.6511(3) 0.1708(2) 0.3555(2) 0.0427(7) Uani 1 1 d . . . C13 C 0.5580(2) 0.2304(2) 0.3667(2) 0.0374(6) Uani 1 1 d . . . C14 C 0.4572(3) 0.1919(2) 0.3669(3) 0.0454(8) Uani 1 1 d . . . H14 H 0.4474 0.1308 0.3596 0.055 Uiso 1 1 calc R . . C15 C 0.3699(3) 0.2445(2) 0.3781(3) 0.0452(8) Uani 1 1 d . . . C16 C 0.3834(3) 0.3356(2) 0.3887(2) 0.0408(7) Uani 1 1 d . . . H16 H 0.3246 0.3710 0.3954 0.049 Uiso 1 1 calc R . . C17 C 0.4862(3) 0.37299(19) 0.3890(2) 0.0374(7) Uani 1 1 d . . . C18 C 0.5739(2) 0.3212(2) 0.3774(2) 0.0379(6) Uani 1 1 d . . . H18 H 0.6422 0.3470 0.3768 0.045 Uiso 1 1 calc R . . C19 C 0.1782(3) 0.2464(2) 0.3830(3) 0.0488(8) Uani 1 1 d . . . H19A H 0.1486 0.2824 0.3253 0.059 Uiso 1 1 calc R . . H19B H 0.1983 0.2853 0.4389 0.059 Uiso 1 1 calc R . . C21 C 0.5906(3) 0.5100(2) 0.3994(3) 0.0498(8) Uani 1 1 d . . . H21A H 0.6589 0.4764 0.4329 0.060 Uiso 1 1 calc R . . H21B H 0.5949 0.5666 0.4320 0.060 Uiso 1 1 calc R . . C22 C 0.5873(3) 0.5259(2) 0.2964(2) 0.0433(7) Uani 1 1 d . . . N1 N 0.0140(3) -0.1714(2) 0.4018(2) 0.0540(7) Uani 1 1 d . . . N2 N 0.2121(3) -0.0689(2) 0.4047(2) 0.0524(7) Uani 1 1 d . A . O1W O 0.6929(4) 0.9184(3) 0.3470(4) 0.1404(17) Uani 1 1 d U . . O3 O 0.74449(19) 0.20887(17) 0.35820(19) 0.0525(6) Uani 1 1 d . . . O4 O 0.6350(2) 0.09075(17) 0.3451(2) 0.0651(7) Uani 1 1 d . . . O5 O 0.2746(2) 0.19874(17) 0.3799(3) 0.0699(9) Uani 1 1 d . . . O8 O 0.4923(2) 0.46281(14) 0.40394(18) 0.0478(6) Uani 1 1 d . . . O9 O 0.6630(2) 0.57741(17) 0.28577(18) 0.0554(6) Uani 1 1 d . . . O10 O 0.5096(2) 0.49044(18) 0.23171(18) 0.0572(7) 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 O2W 0.128(8) 0.101(6) 0.147(8) 0.043(5) 0.025(6) 0.026(5) O3W 0.162(11) 0.162(10) 0.203(12) -0.045(9) 0.092(9) -0.019(8) N3A 0.070(6) 0.061(5) 0.078(4) -0.010(3) 0.029(4) 0.002(5) O1A 0.076(4) 0.067(6) 0.124(5) -0.007(4) 0.034(4) 0.012(4) O1B 0.059(6) 0.058(6) 0.152(10) -0.026(6) 0.041(6) 0.024(5) N3B 0.055(6) 0.040(7) 0.091(7) -0.017(5) 0.021(5) 0.016(5) C3 0.132(4) 0.057(2) 0.077(3) -0.010(2) 0.005(3) 0.007(3) C5 0.097(3) 0.078(3) 0.069(2) -0.011(2) 0.009(2) 0.048(2) O2 0.0280(10) 0.0406(11) 0.0474(12) 0.0019(9) 0.0154(9) 0.0058(8) Zn2 0.0289(2) 0.0436(2) 0.0551(2) 0.00410(16) 0.01870(16) 0.01036(14) Zn1 0.0363(2) 0.0431(2) 0.0487(2) 0.00290(15) 0.02065(16) 0.01273(15) O7 0.0279(12) 0.0590(15) 0.0931(19) 0.0137(13) 0.0267(12) 0.0061(11) O6 0.0353(12) 0.0484(13) 0.0745(17) 0.0084(12) 0.0226(11) 0.0017(10) C20 0.0325(15) 0.0487(18) 0.0517(18) -0.0004(15) 0.0220(14) 0.0000(14) C1 0.094(3) 0.067(3) 0.052(2) -0.004(2) 0.016(2) -0.014(3) C2 0.116(4) 0.070(3) 0.070(3) -0.006(2) 0.013(2) -0.026(3) C4 0.103(3) 0.053(2) 0.057(2) -0.0065(18) 0.006(2) 0.024(2) C6 0.078(3) 0.083(3) 0.051(2) -0.0037(19) 0.0119(18) 0.048(2) C7 0.067(3) 0.123(4) 0.079(3) -0.001(3) 0.029(2) 0.049(3) C8 0.061(2) 0.119(4) 0.096(3) 0.004(3) 0.039(2) 0.024(3) C9 0.054(2) 0.089(3) 0.086(3) 0.013(2) 0.036(2) 0.016(2) C10 0.057(2) 0.062(2) 0.0466(19) 0.0016(17) 0.0165(16) 0.0306(19) C11 0.079(3) 0.0456(19) 0.0397(18) -0.0029(15) 0.0095(17) 0.0220(19) C12 0.0303(15) 0.0479(19) 0.0530(19) 0.0088(15) 0.0178(13) 0.0108(14) C13 0.0273(14) 0.0414(16) 0.0473(17) 0.0055(13) 0.0174(12) 0.0076(12) C14 0.0334(16) 0.0344(16) 0.074(2) -0.0008(15) 0.0247(15) 0.0024(13) C15 0.0304(16) 0.0416(17) 0.070(2) -0.0023(15) 0.0253(15) -0.0008(13) C16 0.0329(15) 0.0402(16) 0.0556(19) 0.0004(14) 0.0230(14) 0.0072(13) C17 0.0414(17) 0.0341(15) 0.0417(16) 0.0017(12) 0.0201(13) 0.0011(12) C18 0.0296(14) 0.0434(16) 0.0451(17) 0.0024(13) 0.0181(13) 0.0005(12) C19 0.0317(16) 0.0474(19) 0.075(2) 0.0035(16) 0.0284(16) 0.0033(14) C21 0.064(2) 0.0409(17) 0.051(2) -0.0075(15) 0.0284(17) -0.0142(16) C22 0.0447(18) 0.0393(17) 0.0496(19) -0.0010(14) 0.0205(15) -0.0053(14) N1 0.0650(19) 0.0485(17) 0.0477(17) -0.0035(13) 0.0168(14) 0.0048(16) N2 0.0471(16) 0.0588(18) 0.0559(18) 0.0058(14) 0.0229(14) 0.0201(14) O1W 0.102(3) 0.077(2) 0.219(4) -0.011(3) 0.017(3) 0.003(2) O3 0.0318(12) 0.0551(14) 0.0784(17) 0.0039(12) 0.0285(11) 0.0117(10) O4 0.0521(15) 0.0435(15) 0.104(2) 0.0020(14) 0.0306(15) 0.0163(12) O5 0.0368(13) 0.0450(14) 0.143(3) -0.0112(15) 0.0505(16) -0.0055(11) O8 0.0596(15) 0.0344(11) 0.0636(15) -0.0058(10) 0.0396(12) -0.0040(10) O9 0.0533(14) 0.0648(16) 0.0514(14) -0.0039(12) 0.0216(11) -0.0238(13) O10 0.0569(15) 0.0685(17) 0.0473(14) 0.0013(12) 0.0181(12) -0.0250(13) _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 N3A O1A 1.356(14) . ? N3A C5 1.422(16) . ? O1B N3B 1.48(2) . ? N3B C5 1.341(17) . ? C3 C2 1.368(8) . ? C3 C4 1.377(8) . ? C3 H3 0.9300 . ? C5 C4 1.465(7) . ? C5 C6 1.487(8) . ? O2 Zn2 1.956(2) . ? O2 Zn1 2.074(2) 3_556 ? O2 Zn1 2.079(2) . ? O2 H2O 0.8338 . ? Zn2 O3 1.925(2) 1_455 ? Zn2 O9 1.981(2) 2_545 ? Zn2 O7 1.983(2) . ? Zn1 O10 2.071(2) 2_545 ? Zn1 O2 2.074(2) 3_556 ? Zn1 O6 2.088(2) . ? Zn1 N2 2.171(3) . ? Zn1 N1 2.307(3) . ? Zn1 Zn1 3.1244(7) 3_556 ? O7 C20 1.262(4) . ? O6 C20 1.232(4) . ? C20 C19 1.514(4) . ? C1 N1 1.334(6) . ? C1 C2 1.414(7) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C4 C11 1.411(5) . ? C6 C7 1.381(7) . ? C6 C10 1.403(5) . ? C7 C8 1.370(8) . ? C7 H7 0.9300 . ? C8 C9 1.377(6) . ? C8 H8 0.9300 . ? C9 N2 1.347(5) . ? C9 H9 0.9300 . ? C10 N2 1.320(5) . ? C10 C11 1.430(6) . ? C11 N1 1.330(5) . ? C12 O4 1.224(4) . ? C12 O3 1.276(4) . ? C12 C13 1.505(4) . ? C13 C14 1.373(4) . ? C13 C18 1.384(4) . ? C14 C15 1.388(4) . ? C14 H14 0.9300 . ? C15 O5 1.368(4) . ? C15 C16 1.385(5) . ? C16 C17 1.386(4) . ? C16 H16 0.9300 . ? C17 O8 1.369(4) . ? C17 C18 1.387(4) . ? C18 H18 0.9300 . ? C19 O5 1.402(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C21 O8 1.424(4) . ? C21 C22 1.509(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 O10 1.231(4) . ? C22 O9 1.262(4) . ? O3 Zn2 1.925(2) 1_655 ? O9 Zn2 1.981(2) 2 ? O10 Zn1 2.071(2) 2 ? 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 O1A N3A C5 97.7(11) . . ? C5 N3B O1B 97.7(12) . . ? C2 C3 C4 117.9(5) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? N3B C5 N3A 46.0(5) . . ? N3B C5 C4 101.0(7) . . ? N3A C5 C4 146.7(6) . . ? N3B C5 C6 151.1(7) . . ? N3A C5 C6 105.5(5) . . ? C4 C5 C6 107.8(4) . . ? Zn2 O2 Zn1 129.05(11) . 3_556 ? Zn2 O2 Zn1 104.01(9) . . ? Zn1 O2 Zn1 97.61(9) 3_556 . ? Zn2 O2 H2O 106.2 . . ? Zn1 O2 H2O 104.9 3_556 . ? Zn1 O2 H2O 115.5 . . ? O3 Zn2 O2 119.83(9) 1_455 . ? O3 Zn2 O9 117.66(11) 1_455 2_545 ? O2 Zn2 O9 105.85(10) . 2_545 ? O3 Zn2 O7 99.45(11) 1_455 . ? O2 Zn2 O7 112.21(10) . . ? O9 Zn2 O7 99.92(12) 2_545 . ? O10 Zn1 O2 174.60(8) 2_545 3_556 ? O10 Zn1 O2 92.81(9) 2_545 . ? O2 Zn1 O2 82.39(9) 3_556 . ? O10 Zn1 O6 88.75(11) 2_545 . ? O2 Zn1 O6 89.12(9) 3_556 . ? O2 Zn1 O6 94.17(8) . . ? O10 Zn1 N2 88.40(10) 2_545 . ? O2 Zn1 N2 96.42(10) 3_556 . ? O2 Zn1 N2 178.72(10) . . ? O6 Zn1 N2 86.26(11) . . ? O10 Zn1 N1 89.14(11) 2_545 . ? O2 Zn1 N1 94.11(9) 3_556 . ? O2 Zn1 N1 99.67(10) . . ? O6 Zn1 N1 166.09(10) . . ? N2 Zn1 N1 79.94(12) . . ? O10 Zn1 Zn1 133.90(7) 2_545 3_556 ? O2 Zn1 Zn1 41.25(5) 3_556 3_556 ? O2 Zn1 Zn1 41.13(6) . 3_556 ? O6 Zn1 Zn1 92.19(7) . 3_556 ? N2 Zn1 Zn1 137.67(8) . 3_556 ? N1 Zn1 Zn1 99.16(8) . 3_556 ? C20 O7 Zn2 121.7(2) . . ? C20 O6 Zn1 137.3(2) . . ? O6 C20 O7 125.7(3) . . ? O6 C20 C19 118.9(3) . . ? O7 C20 C19 115.4(3) . . ? N1 C1 C2 121.9(5) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 121.6(5) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C3 C4 C11 116.2(5) . . ? C3 C4 C5 136.8(5) . . ? C11 C4 C5 107.0(5) . . ? C7 C6 C10 116.8(5) . . ? C7 C6 C5 137.7(4) . . ? C10 C6 C5 105.5(5) . . ? C8 C7 C6 117.9(4) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C7 C8 C9 121.1(5) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? N2 C9 C8 122.8(5) . . ? N2 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? N2 C10 C6 126.4(4) . . ? N2 C10 C11 122.7(3) . . ? C6 C10 C11 110.9(4) . . ? N1 C11 C4 127.6(4) . . ? N1 C11 C10 123.6(3) . . ? C4 C11 C10 108.8(4) . . ? O4 C12 O3 123.7(3) . . ? O4 C12 C13 120.1(3) . . ? O3 C12 C13 116.1(3) . . ? C14 C13 C18 120.9(3) . . ? C14 C13 C12 118.1(3) . . ? C18 C13 C12 121.1(3) . . ? C13 C14 C15 119.7(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? O5 C15 C16 124.8(3) . . ? O5 C15 C14 114.6(3) . . ? C16 C15 C14 120.6(3) . . ? C15 C16 C17 118.7(3) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? O8 C17 C16 114.0(3) . . ? O8 C17 C18 124.8(3) . . ? C16 C17 C18 121.2(3) . . ? C13 C18 C17 118.8(3) . . ? C13 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? O5 C19 C20 107.4(3) . . ? O5 C19 H19A 110.2 . . ? C20 C19 H19A 110.2 . . ? O5 C19 H19B 110.2 . . ? C20 C19 H19B 110.2 . . ? H19A C19 H19B 108.5 . . ? O8 C21 C22 111.9(3) . . ? O8 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? O8 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? O10 C22 O9 126.6(3) . . ? O10 C22 C21 117.6(3) . . ? O9 C22 C21 115.8(3) . . ? C11 N1 C1 114.8(4) . . ? C11 N1 Zn1 104.4(3) . . ? C1 N1 Zn1 140.7(3) . . ? C10 N2 C9 115.1(3) . . ? C10 N2 Zn1 109.4(2) . . ? C9 N2 Zn1 135.5(3) . . ? C12 O3 Zn2 111.7(2) . 1_655 ? C15 O5 C19 118.9(3) . . ? C17 O8 C21 119.3(3) . . ? C22 O9 Zn2 118.4(2) . 2 ? C22 O10 Zn1 140.8(2) . 2 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1B N3B C5 N3A 0.6(8) . . . . ? O1B N3B C5 C4 176.5(7) . . . . ? O1B N3B C5 C6 -10.0(17) . . . . ? O1A N3A C5 N3B 5.8(8) . . . . ? O1A N3A C5 C4 -1.5(11) . . . . ? O1A N3A C5 C6 -179.4(5) . . . . ? Zn1 O2 Zn2 O3 -50.79(17) 3_556 . . 1_455 ? Zn1 O2 Zn2 O3 -163.00(10) . . . 1_455 ? Zn1 O2 Zn2 O9 173.23(12) 3_556 . . 2_545 ? Zn1 O2 Zn2 O9 61.01(12) . . . 2_545 ? Zn1 O2 Zn2 O7 65.22(16) 3_556 . . . ? Zn1 O2 Zn2 O7 -47.00(13) . . . . ? Zn2 O2 Zn1 O10 -44.00(12) . . . 2_545 ? Zn1 O2 Zn1 O10 -177.50(10) 3_556 . . 2_545 ? Zn2 O2 Zn1 O2 133.50(13) . . . 3_556 ? Zn1 O2 Zn1 O2 0.0 3_556 . . 3_556 ? Zn2 O2 Zn1 O6 44.94(11) . . . . ? Zn1 O2 Zn1 O6 -88.56(10) 3_556 . . . ? Zn2 O2 Zn1 N2 154(5) . . . . ? Zn1 O2 Zn1 N2 21(5) 3_556 . . . ? Zn2 O2 Zn1 N1 -133.61(10) . . . . ? Zn1 O2 Zn1 N1 92.90(10) 3_556 . . . ? Zn2 O2 Zn1 Zn1 133.50(13) . . . 3_556 ? O3 Zn2 O7 C20 154.9(3) 1_455 . . . ? O2 Zn2 O7 C20 27.1(3) . . . . ? O9 Zn2 O7 C20 -84.6(3) 2_545 . . . ? O10 Zn1 O6 C20 47.8(3) 2_545 . . . ? O2 Zn1 O6 C20 -127.2(3) 3_556 . . . ? O2 Zn1 O6 C20 -44.9(3) . . . . ? N2 Zn1 O6 C20 136.3(3) . . . . ? N1 Zn1 O6 C20 129.1(4) . . . . ? Zn1 Zn1 O6 C20 -86.1(3) 3_556 . . . ? Zn1 O6 C20 O7 25.0(6) . . . . ? Zn1 O6 C20 C19 -157.2(3) . . . . ? Zn2 O7 C20 O6 -10.6(5) . . . . ? Zn2 O7 C20 C19 171.5(2) . . . . ? C4 C3 C2 C1 -0.7(8) . . . . ? N1 C1 C2 C3 -0.4(7) . . . . ? C2 C3 C4 C11 0.7(7) . . . . ? C2 C3 C4 C5 -176.9(5) . . . . ? N3B C5 C4 C3 -5.8(9) . . . . ? N3A C5 C4 C3 -0.4(13) . . . . ? C6 C5 C4 C3 177.5(5) . . . . ? N3B C5 C4 C11 176.5(6) . . . . ? N3A C5 C4 C11 -178.1(8) . . . . ? C6 C5 C4 C11 -0.2(5) . . . . ? N3B C5 C6 C7 6.8(16) . . . . ? N3A C5 C6 C7 -1.1(8) . . . . ? C4 C5 C6 C7 -179.9(5) . . . . ? N3B C5 C6 C10 -172.8(13) . . . . ? N3A C5 C6 C10 179.4(4) . . . . ? C4 C5 C6 C10 0.6(5) . . . . ? C10 C6 C7 C8 -0.7(6) . . . . ? C5 C6 C7 C8 179.8(5) . . . . ? C6 C7 C8 C9 0.6(7) . . . . ? C7 C8 C9 N2 -0.1(8) . . . . ? C7 C6 C10 N2 0.5(6) . . . . ? C5 C6 C10 N2 -179.8(4) . . . . ? C7 C6 C10 C11 179.6(4) . . . . ? C5 C6 C10 C11 -0.7(4) . . . . ? C3 C4 C11 N1 0.4(6) . . . . ? C5 C4 C11 N1 178.6(4) . . . . ? C3 C4 C11 C10 -178.5(4) . . . . ? C5 C4 C11 C10 -0.2(4) . . . . ? N2 C10 C11 N1 0.8(6) . . . . ? C6 C10 C11 N1 -178.3(3) . . . . ? N2 C10 C11 C4 179.8(3) . . . . ? C6 C10 C11 C4 0.6(4) . . . . ? O4 C12 C13 C14 1.4(5) . . . . ? O3 C12 C13 C14 -178.2(3) . . . . ? O4 C12 C13 C18 -179.2(3) . . . . ? O3 C12 C13 C18 1.1(5) . . . . ? C18 C13 C14 C15 -0.1(5) . . . . ? C12 C13 C14 C15 179.3(3) . . . . ? C13 C14 C15 O5 -178.3(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? O5 C15 C16 C17 177.6(3) . . . . ? C14 C15 C16 C17 -0.8(5) . . . . ? C15 C16 C17 O8 -177.4(3) . . . . ? C15 C16 C17 C18 1.1(5) . . . . ? C14 C13 C18 C17 0.4(5) . . . . ? C12 C13 C18 C17 -179.0(3) . . . . ? O8 C17 C18 C13 177.4(3) . . . . ? C16 C17 C18 C13 -0.9(5) . . . . ? O6 C20 C19 O5 25.5(4) . . . . ? O7 C20 C19 O5 -156.5(3) . . . . ? O8 C21 C22 O10 -6.7(5) . . . . ? O8 C21 C22 O9 170.7(3) . . . . ? C4 C11 N1 C1 -1.4(5) . . . . ? C10 C11 N1 C1 177.3(3) . . . . ? C4 C11 N1 Zn1 -179.3(3) . . . . ? C10 C11 N1 Zn1 -0.6(4) . . . . ? C2 C1 N1 C11 1.4(6) . . . . ? C2 C1 N1 Zn1 178.2(3) . . . . ? O10 Zn1 N1 C11 88.8(2) 2_545 . . . ? O2 Zn1 N1 C11 -95.6(2) 3_556 . . . ? O2 Zn1 N1 C11 -178.5(2) . . . . ? O6 Zn1 N1 C11 7.5(6) . . . . ? N2 Zn1 N1 C11 0.2(2) . . . . ? Zn1 Zn1 N1 C11 -136.8(2) 3_556 . . . ? O10 Zn1 N1 C1 -88.2(4) 2_545 . . . ? O2 Zn1 N1 C1 87.4(4) 3_556 . . . ? O2 Zn1 N1 C1 4.5(4) . . . . ? O6 Zn1 N1 C1 -169.5(4) . . . . ? N2 Zn1 N1 C1 -176.8(4) . . . . ? Zn1 Zn1 N1 C1 46.2(4) 3_556 . . . ? C6 C10 N2 C9 -0.1(6) . . . . ? C11 C10 N2 C9 -179.0(4) . . . . ? C6 C10 N2 Zn1 178.5(3) . . . . ? C11 C10 N2 Zn1 -0.5(4) . . . . ? C8 C9 N2 C10 -0.2(6) . . . . ? C8 C9 N2 Zn1 -178.2(4) . . . . ? O10 Zn1 N2 C10 -89.3(2) 2_545 . . . ? O2 Zn1 N2 C10 93.2(2) 3_556 . . . ? O2 Zn1 N2 C10 72(5) . . . . ? O6 Zn1 N2 C10 -178.1(2) . . . . ? N1 Zn1 N2 C10 0.1(2) . . . . ? Zn1 Zn1 N2 C10 92.7(3) 3_556 . . . ? O10 Zn1 N2 C9 88.8(4) 2_545 . . . ? O2 Zn1 N2 C9 -88.7(4) 3_556 . . . ? O2 Zn1 N2 C9 -110(5) . . . . ? O6 Zn1 N2 C9 0.0(4) . . . . ? N1 Zn1 N2 C9 178.2(4) . . . . ? Zn1 Zn1 N2 C9 -89.2(4) 3_556 . . . ? O4 C12 O3 Zn2 -0.5(4) . . . 1_655 ? C13 C12 O3 Zn2 179.1(2) . . . 1_655 ? C16 C15 O5 C19 6.6(6) . . . . ? C14 C15 O5 C19 -174.9(3) . . . . ? C20 C19 O5 C15 -177.3(3) . . . . ? C16 C17 O8 C21 -175.8(3) . . . . ? C18 C17 O8 C21 5.8(5) . . . . ? C22 C21 O8 C17 78.1(4) . . . . ? O10 C22 O9 Zn2 11.7(5) . . . 2 ? C21 C22 O9 Zn2 -165.5(2) . . . 2 ? O9 C22 O10 Zn1 3.3(7) . . . 2 ? C21 C22 O10 Zn1 -179.5(3) . . . 2 ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.706 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.076 data_3 _database_code_depnum_ccdc_archive 'CCDC 771705' #TrackingRef '- CIF 1-5-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N3 O14 Zn2' _chemical_formula_weight 683.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 14.8390(6) _cell_length_b 15.7170(6) _cell_length_c 22.0810(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5149.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 160 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2776 _exptl_absorpt_coefficient_mu 1.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6636 _exptl_absorpt_correction_T_max 0.7727 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28931 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.73 _reflns_number_total 6056 _reflns_number_gt 4200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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. All absorption corrections were performed by using the SADABS program. The crystal structure was solved by direct methods and refined with full-matrix least-squares (SHELXTL-97) with atomic coordinates and anisotropic thermal parameters for all nonhydrogen atoms. The hydrogen atoms of aromatic rings were included in the structure factor calculation at idealized positions by using a riding model. Some of the water H atoms could not be positioned reliably. ; _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^)+(0.0503P)^2^+4.7358P] 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 6056 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 Zn2 Zn 0.59226(3) 0.13091(2) 0.850651(14) 0.02604(10) Uani 1 1 d . . . Zn1 Zn 0.59929(2) 0.21639(2) 0.722878(14) 0.02440(10) Uani 1 1 d . . . O4 O 0.62078(16) 0.02870(13) 0.80169(9) 0.0296(5) Uani 1 1 d . . . C18 C 0.6061(2) 0.02350(18) 0.74495(13) 0.0242(6) Uani 1 1 d . . . O8 O 0.59746(15) -0.28828(13) 0.76511(10) 0.0310(5) Uani 1 1 d . . . C22 C 0.7428(2) -0.30214(19) 0.81412(13) 0.0276(7) Uani 1 1 d . . . O3 O 0.59023(16) 0.08533(13) 0.71130(9) 0.0311(5) Uani 1 1 d . . . O10 O 0.78401(16) -0.32287(15) 0.86186(9) 0.0365(5) Uani 1 1 d . . . C16 C 0.6009(2) -0.21541(18) 0.73142(13) 0.0258(6) Uani 1 1 d . . . N1 N 0.65061(19) 0.22366(15) 0.62946(11) 0.0289(6) Uani 1 1 d . . . O6 O 0.54928(16) -0.08828(14) 0.42749(9) 0.0348(5) Uani 1 1 d . . . O9 O 0.77505(15) -0.29275(15) 0.76272(9) 0.0353(5) Uani 1 1 d . . . O2 O 0.53389(13) 0.22344(12) 0.80687(8) 0.0240(4) Uiso 1 1 d . . . O5 O 0.5537(2) -0.17407(14) 0.57474(9) 0.0476(7) Uani 1 1 d . . . O7 O 0.5653(2) -0.22059(15) 0.46207(10) 0.0483(7) Uani 1 1 d . . . C12 C 0.6038(2) -0.06393(18) 0.71790(12) 0.0244(6) Uani 1 1 d . . . O1 O 0.7413(2) 0.45194(16) 0.47229(11) 0.0542(7) Uani 1 1 d . . . C20 C 0.5537(2) -0.1441(2) 0.46947(13) 0.0309(7) Uani 1 1 d . . . N3 N 0.7220(2) 0.48816(18) 0.52844(13) 0.0431(7) Uani 1 1 d . . . C4 C 0.6944(2) 0.3360(2) 0.55976(14) 0.0320(7) Uani 1 1 d . . . C5 C 0.7006(2) 0.4299(2) 0.56679(14) 0.0349(8) Uani 1 1 d . . . C1 C 0.6634(2) 0.1684(2) 0.58391(15) 0.0364(8) Uani 1 1 d . . . H1 H 0.6534 0.1108 0.5911 0.044 Uiso 1 1 calc R . . C7 C 0.6659(3) 0.5232(2) 0.66415(16) 0.0463(10) Uani 1 1 d . . . H7 H 0.6801 0.5764 0.6484 0.056 Uiso 1 1 calc R . . C6 C 0.6741(2) 0.4499(2) 0.62999(14) 0.0345(8) Uani 1 1 d . . . N2 N 0.6231(2) 0.36191(17) 0.71403(11) 0.0318(6) Uani 1 1 d . . . C10 C 0.6527(2) 0.37317(19) 0.65766(13) 0.0292(7) Uani 1 1 d . . . C9 C 0.6151(3) 0.4339(2) 0.74606(16) 0.0431(9) Uani 1 1 d . . . H9 H 0.5947 0.4302 0.7858 0.052 Uiso 1 1 calc R . . C21 C 0.6427(2) -0.2903(2) 0.82175(13) 0.0302(7) Uani 1 1 d . . . H21A H 0.6188 -0.3366 0.8460 0.036 Uiso 1 1 calc R . . H21B H 0.6315 -0.2376 0.8432 0.036 Uiso 1 1 calc R . . C19 C 0.5463(3) -0.1072(2) 0.53243(13) 0.0352(8) Uani 1 1 d . . . H19A H 0.5939 -0.0659 0.5390 0.042 Uiso 1 1 calc R . . H19B H 0.4888 -0.0786 0.5372 0.042 Uiso 1 1 calc R . . C14 C 0.5744(2) -0.1547(2) 0.63360(13) 0.0299(7) Uani 1 1 d . . . C17 C 0.6130(2) -0.13405(18) 0.75512(13) 0.0275(7) Uani 1 1 d . . . H17 H 0.6273 -0.1270 0.7958 0.033 Uiso 1 1 calc R . . C2 C 0.6910(3) 0.1936(2) 0.52660(16) 0.0434(9) Uani 1 1 d . . . H2 H 0.6986 0.1528 0.4965 0.052 Uiso 1 1 calc R . . C15 C 0.5828(2) -0.2252(2) 0.67054(14) 0.0304(7) Uani 1 1 d . . . H15 H 0.5763 -0.2795 0.6543 0.036 Uiso 1 1 calc R . . C11 C 0.6655(2) 0.30424(19) 0.61519(13) 0.0280(7) Uani 1 1 d . . . C13 C 0.5831(2) -0.0735(2) 0.65650(12) 0.0277(7) Uani 1 1 d . . . H13 H 0.5754 -0.0263 0.6317 0.033 Uiso 1 1 calc R . . C8 C 0.6354(3) 0.5134(2) 0.72330(16) 0.0501(10) Uani 1 1 d . . . H8 H 0.6286 0.5611 0.7478 0.060 Uiso 1 1 calc R . . C3 C 0.7075(3) 0.2786(2) 0.51338(15) 0.0411(8) Uani 1 1 d . . . H3 H 0.7264 0.2959 0.4752 0.049 Uiso 1 1 calc R . . O1W O 0.2234(2) 0.42794(17) 0.60843(11) 0.0592(8) Uani 1 1 d . . . O2W O 0.5951(2) 0.64099(18) 0.38626(12) 0.0658(9) Uani 1 1 d . . . O3W O 0.5755(3) 0.6352(2) 0.54364(17) 0.0836(11) Uani 1 1 d . . . O4W O 0.5579(3) 0.4712(3) 0.4120(2) 0.1244(17) Uani 1 1 d . . . H2O H 0.5493 0.2684 0.8249 0.187 Uiso 1 1 d R . . H1O H 0.7536 0.4925 0.4475 0.187 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn2 0.0385(2) 0.02366(18) 0.01596(16) 0.00145(12) 0.00153(14) -0.00054(16) Zn1 0.0319(2) 0.02345(18) 0.01783(17) 0.00183(12) 0.00033(14) -0.00159(15) O4 0.0464(14) 0.0244(11) 0.0180(10) -0.0031(8) -0.0029(9) 0.0010(10) C18 0.0267(16) 0.0253(14) 0.0206(13) -0.0014(11) 0.0004(12) -0.0016(12) O8 0.0367(13) 0.0253(11) 0.0312(11) 0.0052(9) -0.0050(10) 0.0015(10) C22 0.0355(18) 0.0232(15) 0.0240(14) 0.0001(12) 0.0002(13) 0.0027(13) O3 0.0492(14) 0.0198(11) 0.0243(10) 0.0005(8) -0.0024(10) -0.0004(10) O10 0.0398(14) 0.0454(14) 0.0242(11) 0.0016(10) -0.0011(10) 0.0097(11) C16 0.0279(16) 0.0242(15) 0.0254(14) 0.0017(11) 0.0001(12) 0.0009(13) N1 0.0367(16) 0.0238(13) 0.0261(13) 0.0040(10) 0.0034(11) -0.0011(12) O6 0.0510(15) 0.0360(12) 0.0176(10) -0.0006(9) 0.0019(10) 0.0077(11) O9 0.0309(13) 0.0493(14) 0.0257(11) 0.0047(10) 0.0046(9) 0.0044(11) O5 0.098(2) 0.0279(12) 0.0166(10) -0.0023(9) -0.0073(12) -0.0039(13) O7 0.082(2) 0.0360(14) 0.0274(12) -0.0079(10) 0.0029(12) 0.0091(13) C12 0.0289(16) 0.0227(15) 0.0216(13) -0.0021(11) 0.0014(12) -0.0003(12) O1 0.081(2) 0.0455(15) 0.0356(13) 0.0064(11) 0.0204(14) 0.0002(15) C20 0.0358(19) 0.0368(19) 0.0202(14) -0.0027(13) -0.0004(13) 0.0037(15) N3 0.058(2) 0.0355(16) 0.0355(15) 0.0083(13) 0.0129(14) -0.0014(15) C4 0.0364(19) 0.0316(17) 0.0280(16) 0.0077(13) 0.0071(13) 0.0013(14) C5 0.045(2) 0.0297(17) 0.0303(16) 0.0068(13) 0.0065(14) -0.0011(15) C1 0.044(2) 0.0273(17) 0.0377(18) 0.0006(14) 0.0056(15) -0.0002(15) C7 0.072(3) 0.0237(17) 0.044(2) 0.0017(15) 0.0075(19) -0.0115(18) C6 0.044(2) 0.0264(16) 0.0330(16) 0.0043(13) 0.0064(15) -0.0001(15) N2 0.0401(17) 0.0307(15) 0.0246(13) 0.0028(11) 0.0011(11) -0.0023(12) C10 0.0334(18) 0.0275(16) 0.0267(15) 0.0033(12) 0.0031(13) -0.0020(13) C9 0.060(3) 0.042(2) 0.0269(16) -0.0034(15) 0.0057(16) -0.0046(18) C21 0.0362(19) 0.0311(17) 0.0232(15) 0.0070(12) 0.0022(13) 0.0052(14) C19 0.056(2) 0.0293(17) 0.0200(15) -0.0029(12) 0.0023(14) 0.0018(16) C14 0.043(2) 0.0305(16) 0.0166(13) -0.0024(12) 0.0010(12) 0.0018(14) C17 0.0354(18) 0.0270(15) 0.0200(14) -0.0006(12) -0.0037(12) 0.0005(13) C2 0.059(3) 0.0349(19) 0.0368(19) -0.0077(15) 0.0113(17) 0.0054(17) C15 0.042(2) 0.0233(16) 0.0260(15) -0.0042(12) 0.0006(13) 0.0016(14) C11 0.0316(18) 0.0260(15) 0.0265(15) 0.0053(12) 0.0028(13) -0.0011(13) C13 0.0381(19) 0.0257(15) 0.0191(14) 0.0005(11) 0.0029(12) 0.0019(13) C8 0.079(3) 0.0320(19) 0.039(2) -0.0086(16) 0.010(2) -0.0060(19) C3 0.051(2) 0.0391(19) 0.0328(18) 0.0036(14) 0.0137(16) 0.0022(17) O1W 0.088(2) 0.0493(16) 0.0404(14) 0.0101(12) 0.0186(14) -0.0021(16) O2W 0.112(3) 0.0491(17) 0.0367(15) -0.0061(12) -0.0007(15) 0.0166(17) O3W 0.112(3) 0.057(2) 0.081(2) 0.0147(17) 0.015(2) 0.0032(19) O4W 0.115(4) 0.090(3) 0.168(5) 0.028(3) -0.027(3) -0.025(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 Zn2 O6 1.932(2) 8_556 ? Zn2 O2 1.9493(19) . ? Zn2 O4 1.982(2) . ? Zn2 O10 1.990(2) 7_765 ? Zn2 Zn1 3.1266(4) . ? Zn1 O9 2.067(2) 7_765 ? Zn1 O3 2.080(2) . ? Zn1 O2 2.086(2) 4_656 ? Zn1 O2 2.0962(19) . ? Zn1 N1 2.202(2) . ? Zn1 N2 2.322(3) . ? O4 C18 1.274(3) . ? C18 O3 1.246(3) . ? C18 C12 1.499(4) . ? O8 C16 1.367(3) . ? O8 C21 1.420(4) . ? C22 O9 1.241(3) . ? C22 O10 1.262(3) . ? C22 C21 1.505(4) . ? O10 Zn2 1.990(2) 7_755 ? C16 C15 1.379(4) . ? C16 C17 1.393(4) . ? N1 C11 1.324(4) . ? N1 C1 1.343(4) . ? O6 C20 1.278(4) . ? O6 Zn2 1.932(2) 8 ? O9 Zn1 2.067(2) 7_755 ? O2 Zn1 2.086(2) 4_656 ? O2 H2O 0.8432 . ? O5 C14 1.370(3) . ? O5 C19 1.411(4) . ? O7 C20 1.225(4) . ? C12 C17 1.382(4) . ? C12 C13 1.398(4) . ? O1 N3 1.394(4) . ? O1 H1O 0.8600 . ? C20 C19 1.510(4) . ? N3 C5 1.286(4) . ? C4 C3 1.378(4) . ? C4 C11 1.390(4) . ? C4 C5 1.488(5) . ? C5 C6 1.483(4) . ? C1 C2 1.388(5) . ? C1 H1 0.9300 . ? C7 C6 1.383(5) . ? C7 C8 1.391(5) . ? C7 H7 0.9300 . ? C6 C10 1.388(4) . ? N2 C10 1.332(4) . ? N2 C9 1.340(4) . ? C10 C11 1.445(4) . ? C9 C8 1.380(5) . ? C9 H9 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C14 C13 1.379(4) . ? C14 C15 1.382(4) . ? C17 H17 0.9300 . ? C2 C3 1.389(5) . ? C2 H2 0.9300 . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? C8 H8 0.9300 . ? C3 H3 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 O6 Zn2 O2 123.19(9) 8_556 . ? O6 Zn2 O4 105.57(9) 8_556 . ? O2 Zn2 O4 115.41(8) . . ? O6 Zn2 O10 108.78(9) 8_556 7_765 ? O2 Zn2 O10 101.50(9) . 7_765 ? O4 Zn2 O10 99.59(10) . 7_765 ? O6 Zn2 Zn1 162.22(7) 8_556 . ? O2 Zn2 Zn1 41.13(6) . . ? O4 Zn2 Zn1 81.31(6) . . ? O10 Zn2 Zn1 85.67(6) 7_765 . ? O9 Zn1 O3 92.40(9) 7_765 . ? O9 Zn1 O2 173.08(8) 7_765 4_656 ? O3 Zn1 O2 87.29(8) . 4_656 ? O9 Zn1 O2 92.56(8) 7_765 . ? O3 Zn1 O2 97.54(8) . . ? O2 Zn1 O2 80.63(8) 4_656 . ? O9 Zn1 N1 95.18(10) 7_765 . ? O3 Zn1 N1 87.63(9) . . ? O2 Zn1 N1 91.71(9) 4_656 . ? O2 Zn1 N1 170.50(9) . . ? O9 Zn1 N2 88.12(10) 7_765 . ? O3 Zn1 N2 167.10(9) . . ? O2 Zn1 N2 93.73(9) 4_656 . ? O2 Zn1 N2 95.31(8) . . ? N1 Zn1 N2 79.49(9) . . ? O9 Zn1 Zn2 67.43(6) 7_765 . ? O3 Zn1 Zn2 71.53(6) . . ? O2 Zn1 Zn2 105.99(5) 4_656 . ? O2 Zn1 Zn2 37.71(5) . . ? N1 Zn1 Zn2 151.55(7) . . ? N2 Zn1 Zn2 120.27(6) . . ? C18 O4 Zn2 123.48(19) . . ? O3 C18 O4 124.7(3) . . ? O3 C18 C12 118.2(2) . . ? O4 C18 C12 117.0(2) . . ? C16 O8 C21 118.7(2) . . ? O9 C22 O10 127.4(3) . . ? O9 C22 C21 117.9(3) . . ? O10 C22 C21 114.6(3) . . ? C18 O3 Zn1 133.40(19) . . ? C22 O10 Zn2 116.0(2) . 7_755 ? O8 C16 C15 115.4(3) . . ? O8 C16 C17 124.7(3) . . ? C15 C16 C17 119.6(3) . . ? C11 N1 C1 114.7(3) . . ? C11 N1 Zn1 109.28(19) . . ? C1 N1 Zn1 135.8(2) . . ? C20 O6 Zn2 112.44(19) . 8 ? C22 O9 Zn1 138.3(2) . 7_755 ? Zn2 O2 Zn1 122.52(10) . 4_656 ? Zn2 O2 Zn1 101.16(9) . . ? Zn1 O2 Zn1 99.04(8) 4_656 . ? Zn2 O2 H2O 105.7 . . ? Zn1 O2 H2O 116.7 4_656 . ? Zn1 O2 H2O 109.7 . . ? C14 O5 C19 118.7(2) . . ? C17 C12 C13 120.8(3) . . ? C17 C12 C18 119.5(2) . . ? C13 C12 C18 119.4(3) . . ? N3 O1 H1O 107.9 . . ? O7 C20 O6 125.7(3) . . ? O7 C20 C19 120.7(3) . . ? O6 C20 C19 113.6(3) . . ? C5 N3 O1 110.2(3) . . ? C3 C4 C11 117.6(3) . . ? C3 C4 C5 135.9(3) . . ? C11 C4 C5 106.5(3) . . ? N3 C5 C6 122.3(3) . . ? N3 C5 C4 130.7(3) . . ? C6 C5 C4 106.9(3) . . ? N1 C1 C2 122.7(3) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C6 C7 C8 116.7(3) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? C7 C6 C10 117.6(3) . . ? C7 C6 C5 135.4(3) . . ? C10 C6 C5 106.9(3) . . ? C10 N2 C9 114.2(3) . . ? C10 N2 Zn1 105.0(2) . . ? C9 N2 Zn1 140.7(2) . . ? N2 C10 C6 127.0(3) . . ? N2 C10 C11 123.4(3) . . ? C6 C10 C11 109.6(3) . . ? N2 C9 C8 123.6(3) . . ? N2 C9 H9 118.2 . . ? C8 C9 H9 118.2 . . ? O8 C21 C22 111.8(2) . . ? O8 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? O8 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? O5 C19 C20 108.5(3) . . ? O5 C19 H19A 110.0 . . ? C20 C19 H19A 110.0 . . ? O5 C19 H19B 110.0 . . ? C20 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? O5 C14 C13 125.1(3) . . ? O5 C14 C15 113.7(3) . . ? C13 C14 C15 121.1(3) . . ? C12 C17 C16 119.7(3) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C1 C2 C3 121.2(3) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? N1 C11 C4 127.2(3) . . ? N1 C11 C10 122.8(3) . . ? C4 C11 C10 110.0(3) . . ? C14 C13 C12 118.4(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C4 C3 C2 116.6(3) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 Zn2 Zn1 O9 160.3(2) 8_556 . . 7_765 ? O2 Zn2 Zn1 O9 128.09(11) . . . 7_765 ? O4 Zn2 Zn1 O9 -85.30(10) . . . 7_765 ? O10 Zn2 Zn1 O9 15.11(10) 7_765 . . 7_765 ? O6 Zn2 Zn1 O3 -98.9(2) 8_556 . . . ? O2 Zn2 Zn1 O3 -131.16(11) . . . . ? O4 Zn2 Zn1 O3 15.45(10) . . . . ? O10 Zn2 Zn1 O3 115.86(10) 7_765 . . . ? O6 Zn2 Zn1 O2 -17.4(2) 8_556 . . 4_656 ? O2 Zn2 Zn1 O2 -49.64(8) . . . 4_656 ? O4 Zn2 Zn1 O2 96.96(9) . . . 4_656 ? O10 Zn2 Zn1 O2 -162.63(9) 7_765 . . 4_656 ? O6 Zn2 Zn1 O2 32.2(2) 8_556 . . . ? O4 Zn2 Zn1 O2 146.61(11) . . . . ? O10 Zn2 Zn1 O2 -112.98(11) 7_765 . . . ? O6 Zn2 Zn1 N1 -143.9(3) 8_556 . . . ? O2 Zn2 Zn1 N1 -176.09(17) . . . . ? O4 Zn2 Zn1 N1 -29.48(16) . . . . ? O10 Zn2 Zn1 N1 70.93(16) 7_765 . . . ? O6 Zn2 Zn1 N2 86.8(2) 8_556 . . . ? O2 Zn2 Zn1 N2 54.58(12) . . . . ? O4 Zn2 Zn1 N2 -158.82(11) . . . . ? O10 Zn2 Zn1 N2 -58.41(11) 7_765 . . . ? O6 Zn2 O4 C18 142.4(2) 8_556 . . . ? O2 Zn2 O4 C18 2.8(3) . . . . ? O10 Zn2 O4 C18 -104.9(2) 7_765 . . . ? Zn1 Zn2 O4 C18 -20.8(2) . . . . ? Zn2 O4 C18 O3 15.5(4) . . . . ? Zn2 O4 C18 C12 -161.6(2) . . . . ? O4 C18 O3 Zn1 11.3(5) . . . . ? C12 C18 O3 Zn1 -171.6(2) . . . . ? O9 Zn1 O3 C18 45.7(3) 7_765 . . . ? O2 Zn1 O3 C18 -127.4(3) 4_656 . . . ? O2 Zn1 O3 C18 -47.2(3) . . . . ? N1 Zn1 O3 C18 140.8(3) . . . . ? N2 Zn1 O3 C18 137.7(4) . . . . ? Zn2 Zn1 O3 C18 -19.5(3) . . . . ? O9 C22 O10 Zn2 -14.0(4) . . . 7_755 ? C21 C22 O10 Zn2 164.2(2) . . . 7_755 ? C21 O8 C16 C15 159.4(3) . . . . ? C21 O8 C16 C17 -26.5(4) . . . . ? O9 Zn1 N1 C11 -89.3(2) 7_765 . . . ? O3 Zn1 N1 C11 178.6(2) . . . . ? O2 Zn1 N1 C11 91.3(2) 4_656 . . . ? O2 Zn1 N1 C11 55.3(6) . . . . ? N2 Zn1 N1 C11 -2.1(2) . . . . ? Zn2 Zn1 N1 C11 -139.35(18) . . . . ? O9 Zn1 N1 C1 96.7(3) 7_765 . . . ? O3 Zn1 N1 C1 4.5(3) . . . . ? O2 Zn1 N1 C1 -82.7(3) 4_656 . . . ? O2 Zn1 N1 C1 -118.7(5) . . . . ? N2 Zn1 N1 C1 -176.2(3) . . . . ? Zn2 Zn1 N1 C1 46.6(4) . . . . ? O10 C22 O9 Zn1 -12.0(5) . . . 7_755 ? C21 C22 O9 Zn1 169.9(2) . . . 7_755 ? O6 Zn2 O2 Zn1 -60.37(14) 8_556 . . 4_656 ? O4 Zn2 O2 Zn1 71.38(13) . . . 4_656 ? O10 Zn2 O2 Zn1 177.93(11) 7_765 . . 4_656 ? Zn1 Zn2 O2 Zn1 108.41(13) . . . 4_656 ? O6 Zn2 O2 Zn1 -168.78(8) 8_556 . . . ? O4 Zn2 O2 Zn1 -37.03(12) . . . . ? O10 Zn2 O2 Zn1 69.52(9) 7_765 . . . ? O9 Zn1 O2 Zn2 -46.67(10) 7_765 . . . ? O3 Zn1 O2 Zn2 46.08(10) . . . . ? O2 Zn1 O2 Zn2 132.06(6) 4_656 . . . ? N1 Zn1 O2 Zn2 168.6(5) . . . . ? N2 Zn1 O2 Zn2 -135.03(10) . . . . ? O9 Zn1 O2 Zn1 -172.57(9) 7_765 . . 4_656 ? O3 Zn1 O2 Zn1 -79.81(9) . . . 4_656 ? O2 Zn1 O2 Zn1 6.16(11) 4_656 . . 4_656 ? N1 Zn1 O2 Zn1 42.7(6) . . . 4_656 ? N2 Zn1 O2 Zn1 99.08(9) . . . 4_656 ? Zn2 Zn1 O2 Zn1 -125.89(12) . . . 4_656 ? O3 C18 C12 C17 -174.2(3) . . . . ? O4 C18 C12 C17 3.1(4) . . . . ? O3 C18 C12 C13 -0.7(4) . . . . ? O4 C18 C12 C13 176.6(3) . . . . ? Zn2 O6 C20 O7 -14.5(5) 8 . . . ? Zn2 O6 C20 C19 163.6(2) 8 . . . ? O1 N3 C5 C6 -178.2(3) . . . . ? O1 N3 C5 C4 0.1(6) . . . . ? C3 C4 C5 N3 -0.3(7) . . . . ? C11 C4 C5 N3 -178.0(4) . . . . ? C3 C4 C5 C6 178.2(4) . . . . ? C11 C4 C5 C6 0.4(4) . . . . ? C11 N1 C1 C2 0.6(5) . . . . ? Zn1 N1 C1 C2 174.4(3) . . . . ? C8 C7 C6 C10 -0.9(6) . . . . ? C8 C7 C6 C5 178.1(4) . . . . ? N3 C5 C6 C7 -1.2(7) . . . . ? C4 C5 C6 C7 -179.8(4) . . . . ? N3 C5 C6 C10 177.9(3) . . . . ? C4 C5 C6 C10 -0.8(4) . . . . ? O9 Zn1 N2 C10 97.0(2) 7_765 . . . ? O3 Zn1 N2 C10 4.5(6) . . . . ? O2 Zn1 N2 C10 -89.7(2) 4_656 . . . ? O2 Zn1 N2 C10 -170.6(2) . . . . ? N1 Zn1 N2 C10 1.4(2) . . . . ? Zn2 Zn1 N2 C10 159.35(19) . . . . ? O9 Zn1 N2 C9 -84.5(4) 7_765 . . . ? O3 Zn1 N2 C9 -177.0(4) . . . . ? O2 Zn1 N2 C9 88.8(4) 4_656 . . . ? O2 Zn1 N2 C9 7.9(4) . . . . ? N1 Zn1 N2 C9 179.9(4) . . . . ? Zn2 Zn1 N2 C9 -22.1(4) . . . . ? C9 N2 C10 C6 -0.9(5) . . . . ? Zn1 N2 C10 C6 178.1(3) . . . . ? C9 N2 C10 C11 -179.4(3) . . . . ? Zn1 N2 C10 C11 -0.5(4) . . . . ? C7 C6 C10 N2 1.3(6) . . . . ? C5 C6 C10 N2 -178.0(3) . . . . ? C7 C6 C10 C11 -179.9(3) . . . . ? C5 C6 C10 C11 0.8(4) . . . . ? C10 N2 C9 C8 0.1(6) . . . . ? Zn1 N2 C9 C8 -178.3(3) . . . . ? C16 O8 C21 C22 -77.8(3) . . . . ? O9 C22 C21 O8 13.1(4) . . . . ? O10 C22 C21 O8 -165.3(3) . . . . ? C14 O5 C19 C20 161.7(3) . . . . ? O7 C20 C19 O5 -0.7(5) . . . . ? O6 C20 C19 O5 -178.9(3) . . . . ? C19 O5 C14 C13 4.5(5) . . . . ? C19 O5 C14 C15 -178.0(3) . . . . ? C13 C12 C17 C16 -0.5(5) . . . . ? C18 C12 C17 C16 172.8(3) . . . . ? O8 C16 C17 C12 -171.6(3) . . . . ? C15 C16 C17 C12 2.2(5) . . . . ? N1 C1 C2 C3 0.4(6) . . . . ? O8 C16 C15 C14 172.6(3) . . . . ? C17 C16 C15 C14 -1.8(5) . . . . ? O5 C14 C15 C16 -178.1(3) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C1 N1 C11 C4 -1.7(5) . . . . ? Zn1 N1 C11 C4 -177.2(3) . . . . ? C1 N1 C11 C10 178.2(3) . . . . ? Zn1 N1 C11 C10 2.8(4) . . . . ? C3 C4 C11 N1 1.7(6) . . . . ? C5 C4 C11 N1 179.9(3) . . . . ? C3 C4 C11 C10 -178.2(3) . . . . ? C5 C4 C11 C10 0.0(4) . . . . ? N2 C10 C11 N1 -1.7(5) . . . . ? C6 C10 C11 N1 179.6(3) . . . . ? N2 C10 C11 C4 178.3(3) . . . . ? C6 C10 C11 C4 -0.5(4) . . . . ? O5 C14 C13 C12 179.5(3) . . . . ? C15 C14 C13 C12 2.1(5) . . . . ? C17 C12 C13 C14 -1.6(5) . . . . ? C18 C12 C13 C14 -175.0(3) . . . . ? N2 C9 C8 C7 0.2(7) . . . . ? C6 C7 C8 C9 0.3(6) . . . . ? C11 C4 C3 C2 -0.4(5) . . . . ? C5 C4 C3 C2 -178.1(4) . . . . ? C1 C2 C3 C4 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.572 _refine_diff_density_min -0.570 _refine_diff_density_rms 0.088 data_4 _database_code_depnum_ccdc_archive 'CCDC 771706' #TrackingRef '- CIF 1-5-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H43.50 N O13.25 Zn3' _chemical_formula_weight 874.31 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' O O 0.0106 0.0060 '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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.3790(5) _cell_length_b 16.3610(5) _cell_length_c 28.9990(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7771.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 256 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3604 _exptl_absorpt_coefficient_mu 1.899 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6380 _exptl_absorpt_correction_T_max 0.7262 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46328 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.28 _reflns_number_total 9420 _reflns_number_gt 5521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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. All absorption corrections were performed by using the SADABS program. The crystal structure was solved by direct methods and refined with full-matrix least-squares 'SHELXTL-97' with atomic coordinates and anisotropic thermal parameters for all nonhydrogen atoms. The hydrogen atoms of aromatic rings were included in the structure factor calculation at idealized positions by using a riding model. H atoms of water molecules were located from difference Fourier maps. C1, C2, C3, C13, C14 and C15 atoms were treated with restained refinement. ; _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^)+(0.0329P)^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 9420 _refine_ls_number_parameters 469 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.930 _refine_ls_shift/su_max 0.002 _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 O1W O 0.8348(7) 0.1357(8) 0.8853(4) 0.101(4) Uani 0.25 1 d P . . N1 N 0.57116(15) 0.33902(17) 0.63586(10) 0.0438(7) Uani 1 1 d . . . O7 O 0.41471(11) 0.71506(11) 0.72163(7) 0.0299(5) Uani 1 1 d . . . C32 C 0.44061(17) 0.64204(18) 0.72849(10) 0.0275(7) Uani 1 1 d . . . C26 C 0.39975(16) 0.59785(17) 0.76793(10) 0.0248(7) Uani 1 1 d . . . C30 C 0.29652(16) 0.59312(17) 0.82711(10) 0.0254(7) Uani 1 1 d . . . C27 C 0.42830(15) 0.52215(17) 0.78220(10) 0.0258(7) Uani 1 1 d . . . H27 H 0.4725 0.4984 0.7671 0.031 Uiso 1 1 calc R . . C29 C 0.32515(16) 0.51764(17) 0.84116(10) 0.0256(7) Uani 1 1 d . . . H29 H 0.3001 0.4908 0.8656 0.031 Uiso 1 1 calc R . . C28 C 0.39151(16) 0.48150(17) 0.81880(10) 0.0235(7) Uani 1 1 d . . . C33 C 0.42168(17) 0.39983(17) 0.83397(10) 0.0254(7) Uani 1 1 d . . . O12 O 0.48483(11) 0.37227(12) 0.81348(7) 0.0315(5) Uani 1 1 d . . . O11 O 0.38343(12) 0.36317(11) 0.86509(7) 0.0320(5) Uani 1 1 d . . . O10 O 0.17972(13) 0.59221(13) 0.87606(8) 0.0458(6) Uani 1 1 d . . . Zn1 Zn 0.540268(18) 0.159908(19) 0.920011(11) 0.02265(9) Uani 1 1 d . . . Zn2 Zn 0.549475(18) 0.277501(19) 0.830717(11) 0.02036(8) Uani 1 1 d . . . Zn3 Zn 0.372893(18) 0.24667(2) 0.882339(11) 0.02214(8) Uani 1 1 d . . . O4 O 0.35022(11) 0.24145(12) 0.94835(7) 0.0316(5) Uani 1 1 d . . . O9 O 0.21953(11) 0.71053(12) 0.84632(7) 0.0340(5) Uani 1 1 d . . . O13 O 0.48011(10) 0.19942(10) 0.86589(6) 0.0204(4) Uani 1 1 d . . . O2 O 0.42905(12) -0.04939(12) 1.07404(8) 0.0392(6) Uani 1 1 d . . . C21 C 0.23347(16) 0.16516(17) 1.07123(10) 0.0250(7) Uani 1 1 d . . . O3 O 0.46100(11) 0.17183(12) 0.97040(7) 0.0360(5) Uani 1 1 d . . . C22 C 0.26333(16) 0.09348(17) 1.09137(10) 0.0266(7) Uani 1 1 d . . . H22 H 0.2363 0.0706 1.1164 0.032 Uiso 1 1 calc R . . C19 C 0.34413(15) 0.16251(17) 1.01659(9) 0.0220(6) Uani 1 1 d . . . C20 C 0.27319(16) 0.19836(17) 1.03324(9) 0.0256(7) Uani 1 1 d . . . H20 H 0.2522 0.2447 1.0189 0.031 Uiso 1 1 calc R . . C18 C 0.37360(16) 0.09270(17) 1.03740(9) 0.0234(6) Uani 1 1 d . . . H18 H 0.4217 0.0694 1.0266 0.028 Uiso 1 1 calc R . . C24 C 0.38813(17) 0.19515(17) 0.97512(10) 0.0251(7) Uani 1 1 d . . . C17 C 0.33329(16) 0.05636(17) 1.07406(10) 0.0239(7) Uani 1 1 d . . . O8 O 0.49426(13) 0.60692(13) 0.70655(8) 0.0446(6) Uani 1 1 d . . . C31 C 0.33400(16) 0.63245(17) 0.79061(10) 0.0265(7) Uani 1 1 d . . . H31 H 0.3146 0.6832 0.7811 0.032 Uiso 1 1 calc R . . O1 O 0.32675(16) -0.05999(16) 1.12317(9) 0.0753(9) Uani 1 1 d . . . C34 C 0.22637(17) 0.63272(19) 0.85205(10) 0.0289(7) Uani 1 1 d . . . C23 C 0.36361(18) -0.02418(19) 1.09318(11) 0.0338(8) Uani 1 1 d . . . C12 C 0.62644(19) 0.3483(2) 0.67783(11) 0.0446(9) Uani 1 1 d . . . H12A H 0.6130 0.3051 0.6995 0.054 Uiso 1 1 calc R . . H12B H 0.6823 0.3395 0.6680 0.054 Uiso 1 1 calc R . . C16 C 0.4834(2) 0.3556(2) 0.64908(14) 0.0608(11) Uani 1 1 d . . . H16A H 0.4495 0.3481 0.6220 0.073 Uiso 1 1 calc R . . H16B H 0.4788 0.4123 0.6584 0.073 Uiso 1 1 calc R . . C11 C 0.6227(2) 0.4286(2) 0.70311(13) 0.0521(10) Uani 1 1 d . . . H11A H 0.5673 0.4386 0.7134 0.062 Uiso 1 1 calc R . . H11B H 0.6382 0.4725 0.6824 0.062 Uiso 1 1 calc R . . C6 C 0.6930(2) 0.4497(2) 0.53964(13) 0.0595(11) Uani 1 1 d . . . H6A H 0.6861 0.5038 0.5528 0.071 Uiso 1 1 calc R . . H6B H 0.6524 0.4433 0.5156 0.071 Uiso 1 1 calc R . . C2 C 0.5569(4) 0.1425(3) 0.56148(19) 0.125(2) Uani 1 1 d U . . H2A H 0.6155 0.1404 0.5565 0.150 Uiso 1 1 calc R . . H2B H 0.5440 0.1052 0.5864 0.150 Uiso 1 1 calc R . . C8 C 0.5944(2) 0.3999(2) 0.59839(12) 0.0461(9) Uani 1 1 d . . . H8A H 0.5535 0.3977 0.5743 0.055 Uiso 1 1 calc R . . H8B H 0.5930 0.4545 0.6115 0.055 Uiso 1 1 calc R . . C13 C 0.3269(3) 0.2551(3) 0.7286(2) 0.128(2) Uani 1 1 d U . . H13A H 0.2694 0.2647 0.7317 0.193 Uiso 1 1 calc R . . H13B H 0.3530 0.2623 0.7580 0.193 Uiso 1 1 calc R . . H13C H 0.3359 0.2003 0.7179 0.193 Uiso 1 1 calc R . . C7 C 0.6773(2) 0.3869(2) 0.57668(12) 0.0466(9) Uani 1 1 d . . . H7A H 0.7192 0.3908 0.6002 0.056 Uiso 1 1 calc R . . H7B H 0.6798 0.3325 0.5634 0.056 Uiso 1 1 calc R . . C15 C 0.4499(2) 0.3018(3) 0.68789(15) 0.0760(13) Uani 1 1 d U . . H15A H 0.4602 0.2448 0.6805 0.091 Uiso 1 1 calc R . . H15B H 0.4786 0.3143 0.7163 0.091 Uiso 1 1 calc R . . C4 C 0.5806(2) 0.2518(2) 0.61897(13) 0.0536(10) Uani 1 1 d . . . H4A H 0.5640 0.2153 0.6436 0.064 Uiso 1 1 calc R . . H4B H 0.6381 0.2419 0.6131 0.064 Uiso 1 1 calc R . . C5 C 0.7769(2) 0.4443(3) 0.51823(15) 0.0822(14) Uani 1 1 d . . . H5A H 0.7826 0.4861 0.4952 0.123 Uiso 1 1 calc R . . H5B H 0.7838 0.3916 0.5042 0.123 Uiso 1 1 calc R . . H5C H 0.8176 0.4519 0.5417 0.123 Uiso 1 1 calc R . . C10 C 0.6795(2) 0.4280(2) 0.74443(13) 0.0631(11) Uani 1 1 d . . . H10A H 0.7352 0.4210 0.7337 0.076 Uiso 1 1 calc R . . H10B H 0.6662 0.3816 0.7638 0.076 Uiso 1 1 calc R . . C14 C 0.3616(3) 0.3136(3) 0.69511(18) 0.0997(16) Uani 1 1 d U . . H14A H 0.3335 0.3074 0.6659 0.120 Uiso 1 1 calc R . . H14B H 0.3520 0.3688 0.7060 0.120 Uiso 1 1 calc R . . C9 C 0.6746(2) 0.5056(3) 0.77322(14) 0.0848(14) Uani 1 1 d . . . H9A H 0.7115 0.5015 0.7988 0.127 Uiso 1 1 calc R . . H9B H 0.6199 0.5124 0.7844 0.127 Uiso 1 1 calc R . . H9C H 0.6893 0.5517 0.7545 0.127 Uiso 1 1 calc R . . C3 C 0.5330(3) 0.2295(2) 0.57590(14) 0.0705(12) Uani 1 1 d U . . H3A H 0.5456 0.2676 0.5513 0.085 Uiso 1 1 calc R . . H3B H 0.4749 0.2321 0.5821 0.085 Uiso 1 1 calc R . . C1 C 0.5154(4) 0.1150(4) 0.5196(3) 0.195(3) Uani 1 1 d U . . H1A H 0.5323 0.0602 0.5124 0.293 Uiso 1 1 calc R . . H1B H 0.5293 0.1506 0.4945 0.293 Uiso 1 1 calc R . . H1C H 0.4574 0.1161 0.5244 0.293 Uiso 1 1 calc R . . C25 C 0.15954(16) 0.20638(18) 1.09106(11) 0.0265(7) Uani 1 1 d . . . O5 O 0.12666(11) 0.26130(12) 1.06701(7) 0.0361(5) Uani 1 1 d . . . O6 O 0.13613(12) 0.18309(12) 1.13019(7) 0.0378(6) Uani 1 1 d . . . H13O H 0.4810 0.1653 0.8447 0.057 Uiso 1 1 d R . . H1BO H 0.8633 0.0971 0.8786 0.057 Uiso 0.25 1 d PR . . H1AO H 0.8141 0.1564 0.8615 0.057 Uiso 0.25 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1W 0.083(9) 0.105(10) 0.114(11) -0.028(9) 0.018(8) -0.050(8) N1 0.0385(16) 0.0465(18) 0.0464(18) 0.0109(15) -0.0047(14) 0.0071(14) O7 0.0372(12) 0.0203(11) 0.0322(12) 0.0079(9) 0.0110(10) 0.0049(10) C32 0.0289(17) 0.0268(18) 0.0267(17) 0.0068(14) 0.0045(13) 0.0029(14) C26 0.0266(15) 0.0211(16) 0.0269(17) 0.0053(13) 0.0064(13) 0.0040(13) C30 0.0241(15) 0.0231(17) 0.0291(18) 0.0014(14) 0.0037(13) 0.0012(13) C27 0.0229(15) 0.0264(17) 0.0279(18) 0.0027(14) 0.0062(13) 0.0067(13) C29 0.0267(16) 0.0249(17) 0.0251(17) 0.0066(13) 0.0053(13) -0.0001(13) C28 0.0237(15) 0.0211(16) 0.0256(17) 0.0038(13) 0.0022(13) 0.0022(12) C33 0.0264(16) 0.0239(17) 0.0258(17) -0.0007(14) -0.0031(14) -0.0022(13) O12 0.0305(11) 0.0297(12) 0.0342(13) 0.0102(10) 0.0080(10) 0.0097(10) O11 0.0400(12) 0.0211(11) 0.0351(12) 0.0098(10) 0.0118(10) 0.0027(10) O10 0.0392(13) 0.0355(13) 0.0627(17) 0.0130(12) 0.0281(12) 0.0056(11) Zn1 0.01802(16) 0.02222(18) 0.02773(19) 0.00613(14) 0.00170(14) 0.00097(15) Zn2 0.01981(16) 0.02003(18) 0.02123(17) -0.00051(14) -0.00058(14) 0.00020(14) Zn3 0.01797(16) 0.02383(18) 0.02462(18) 0.00493(15) -0.00110(14) -0.00075(14) O4 0.0376(12) 0.0318(12) 0.0254(12) 0.0079(10) 0.0091(9) 0.0114(10) O9 0.0309(11) 0.0247(12) 0.0462(14) 0.0061(10) 0.0120(10) 0.0059(10) O13 0.0201(9) 0.0194(10) 0.0217(10) -0.0040(9) -0.0010(8) -0.0007(8) O2 0.0327(12) 0.0282(12) 0.0568(15) 0.0110(11) 0.0084(11) 0.0130(10) C21 0.0231(15) 0.0268(17) 0.0252(17) 0.0014(14) 0.0025(12) 0.0057(13) O3 0.0262(11) 0.0499(14) 0.0319(12) 0.0071(10) 0.0110(10) 0.0075(11) C22 0.0261(16) 0.0302(18) 0.0235(17) 0.0046(14) 0.0043(13) 0.0011(14) C19 0.0205(14) 0.0233(16) 0.0220(16) 0.0014(13) 0.0053(12) 0.0019(13) C20 0.0291(16) 0.0238(17) 0.0239(17) 0.0060(13) 0.0014(13) 0.0080(13) C18 0.0201(14) 0.0258(17) 0.0244(16) -0.0043(13) 0.0007(13) 0.0064(13) C24 0.0274(16) 0.0221(17) 0.0258(17) -0.0010(13) 0.0041(13) 0.0013(13) C17 0.0234(15) 0.0234(17) 0.0249(17) 0.0002(13) 0.0000(13) 0.0066(13) O8 0.0486(14) 0.0397(14) 0.0453(15) 0.0209(11) 0.0272(12) 0.0231(11) C31 0.0258(15) 0.0220(17) 0.0318(18) 0.0038(14) 0.0017(14) 0.0022(13) O1 0.083(2) 0.0621(19) 0.080(2) 0.0461(16) 0.0442(16) 0.0320(16) C34 0.0219(16) 0.0317(19) 0.0332(19) 0.0025(15) 0.0024(14) 0.0031(14) C23 0.0313(18) 0.0312(19) 0.039(2) 0.0048(16) 0.0003(15) 0.0070(15) C12 0.0386(19) 0.051(2) 0.044(2) 0.0131(18) -0.0068(17) 0.0076(18) C16 0.038(2) 0.073(3) 0.072(3) 0.020(2) -0.0055(19) 0.013(2) C11 0.047(2) 0.053(2) 0.056(3) 0.004(2) -0.0022(19) 0.0074(19) C6 0.074(3) 0.058(3) 0.047(2) 0.011(2) -0.001(2) 0.009(2) C2 0.159(4) 0.099(3) 0.117(4) -0.020(3) -0.077(3) 0.003(3) C8 0.053(2) 0.044(2) 0.041(2) 0.0112(18) -0.0069(18) 0.0091(18) C13 0.105(3) 0.123(4) 0.158(4) 0.049(3) 0.035(3) -0.002(3) C7 0.047(2) 0.044(2) 0.049(2) 0.0043(18) -0.0055(18) -0.0031(18) C15 0.051(2) 0.094(3) 0.084(3) 0.031(2) 0.003(2) 0.002(2) C4 0.054(2) 0.044(2) 0.062(3) 0.012(2) -0.014(2) 0.0031(19) C5 0.083(3) 0.089(4) 0.074(3) 0.023(3) 0.019(3) -0.001(3) C10 0.058(3) 0.075(3) 0.056(3) 0.006(2) 0.001(2) -0.002(2) C14 0.071(3) 0.117(3) 0.111(3) 0.035(3) 0.023(3) 0.010(3) C9 0.079(3) 0.107(4) 0.068(3) -0.021(3) 0.001(3) -0.017(3) C3 0.079(3) 0.060(3) 0.071(3) 0.000(2) -0.025(2) 0.000(2) C1 0.213(5) 0.171(5) 0.201(5) -0.012(4) -0.027(4) -0.003(4) C25 0.0223(15) 0.0257(18) 0.0315(18) -0.0012(14) 0.0035(13) 0.0029(13) O5 0.0300(11) 0.0401(14) 0.0380(13) 0.0108(11) 0.0079(10) 0.0180(10) O6 0.0377(12) 0.0423(14) 0.0335(13) 0.0099(11) 0.0186(10) 0.0173(10) _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 O1W H1BO 0.8093 . ? O1W H1AO 0.8398 . ? N1 C16 1.512(4) . ? N1 C4 1.516(4) . ? N1 C8 1.523(4) . ? N1 C12 1.525(4) . ? O7 C32 1.283(3) . ? O7 Zn2 1.9214(18) 4_656 ? C32 O8 1.228(3) . ? C32 C26 1.510(4) . ? C26 C31 1.383(4) . ? C26 C27 1.387(4) . ? C30 C29 1.382(4) . ? C30 C31 1.383(4) . ? C30 C34 1.504(4) . ? C27 C28 1.390(4) . ? C27 H27 0.9300 . ? C29 C28 1.397(4) . ? C29 H29 0.9300 . ? C28 C33 1.491(4) . ? C33 O11 1.252(3) . ? C33 O12 1.275(3) . ? O12 Zn2 1.9429(19) . ? O11 Zn3 1.9780(19) . ? O10 C34 1.228(3) . ? Zn1 O2 1.885(2) 5_657 ? Zn1 O5 1.9508(19) 3_557 ? Zn1 O13 1.9626(17) . ? Zn1 O3 1.9643(18) . ? Zn2 O7 1.9214(18) 4_646 ? Zn2 O6 1.9276(19) 3_557 ? Zn2 O13 1.9908(17) . ? Zn3 O9 1.9319(19) 7_655 ? Zn3 O4 1.9517(19) . ? Zn3 O13 1.9772(17) . ? O4 C24 1.250(3) . ? O9 C34 1.289(3) . ? O9 Zn3 1.9319(18) 7_665 ? O13 H13O 0.8308 . ? O2 C23 1.275(3) . ? O2 Zn1 1.885(2) 5_657 ? C21 C20 1.390(4) . ? C21 C22 1.398(4) . ? C21 C25 1.501(4) . ? O3 C24 1.261(3) . ? C22 C17 1.391(4) . ? C22 H22 0.9300 . ? C19 C18 1.379(4) . ? C19 C20 1.388(3) . ? C19 C24 1.500(4) . ? C20 H20 0.9300 . ? C18 C17 1.386(4) . ? C18 H18 0.9300 . ? C17 C23 1.513(4) . ? C31 H31 0.9300 . ? O1 C23 1.210(4) . ? C12 C11 1.506(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C16 C15 1.531(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C11 C10 1.517(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C6 C7 1.509(4) . ? C6 C5 1.510(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C2 C1 1.463(7) . ? C2 C3 1.534(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C8 C7 1.511(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C13 C14 1.477(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C15 C14 1.474(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C4 C3 1.517(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C10 C9 1.521(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C25 O6 1.257(3) . ? C25 O5 1.258(3) . ? O5 Zn1 1.9508(19) 3_457 ? O6 Zn2 1.9276(19) 3_457 ? 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 H1BO O1W H1AO 110.5 . . ? C16 N1 C4 110.3(3) . . ? C16 N1 C8 107.6(2) . . ? C4 N1 C8 111.1(3) . . ? C16 N1 C12 110.1(3) . . ? C4 N1 C12 106.9(2) . . ? C8 N1 C12 110.8(3) . . ? C32 O7 Zn2 121.11(18) . 4_656 ? O8 C32 O7 126.3(3) . . ? O8 C32 C26 119.1(3) . . ? O7 C32 C26 114.6(2) . . ? C31 C26 C27 119.1(3) . . ? C31 C26 C32 120.6(2) . . ? C27 C26 C32 120.3(2) . . ? C29 C30 C31 119.4(3) . . ? C29 C30 C34 120.1(3) . . ? C31 C30 C34 120.5(3) . . ? C26 C27 C28 120.6(3) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C30 C29 C28 120.3(3) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C27 C28 C29 119.3(3) . . ? C27 C28 C33 120.7(2) . . ? C29 C28 C33 120.0(3) . . ? O11 C33 O12 124.9(3) . . ? O11 C33 C28 118.5(3) . . ? O12 C33 C28 116.6(3) . . ? C33 O12 Zn2 127.19(19) . . ? C33 O11 Zn3 133.45(19) . . ? O2 Zn1 O5 115.02(9) 5_657 3_557 ? O2 Zn1 O13 121.53(8) 5_657 . ? O5 Zn1 O13 107.50(8) 3_557 . ? O2 Zn1 O3 101.74(9) 5_657 . ? O5 Zn1 O3 105.68(9) 3_557 . ? O13 Zn1 O3 103.32(8) . . ? O7 Zn2 O6 114.69(9) 4_646 3_557 ? O7 Zn2 O12 112.80(8) 4_646 . ? O6 Zn2 O12 106.60(9) 3_557 . ? O7 Zn2 O13 103.76(8) 4_646 . ? O6 Zn2 O13 109.48(8) 3_557 . ? O12 Zn2 O13 109.45(7) . . ? O9 Zn3 O4 111.58(9) 7_655 . ? O9 Zn3 O13 116.48(8) 7_655 . ? O4 Zn3 O13 112.86(8) . . ? O9 Zn3 O11 103.10(8) 7_655 . ? O4 Zn3 O11 107.86(8) . . ? O13 Zn3 O11 103.79(8) . . ? C24 O4 Zn3 122.77(18) . . ? C34 O9 Zn3 107.50(18) . 7_665 ? Zn1 O13 Zn3 112.44(8) . . ? Zn1 O13 Zn2 109.55(8) . . ? Zn3 O13 Zn2 112.30(8) . . ? Zn1 O13 H13O 111.1 . . ? Zn3 O13 H13O 117.2 . . ? Zn2 O13 H13O 92.4 . . ? C23 O2 Zn1 119.6(2) . 5_657 ? C20 C21 C22 119.7(3) . . ? C20 C21 C25 120.4(3) . . ? C22 C21 C25 119.9(3) . . ? C24 O3 Zn1 137.44(19) . . ? C17 C22 C21 120.2(3) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C18 C19 C20 119.4(3) . . ? C18 C19 C24 118.5(2) . . ? C20 C19 C24 122.0(3) . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C19 C18 C17 121.6(2) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? O4 C24 O3 125.9(3) . . ? O4 C24 C19 118.4(2) . . ? O3 C24 C19 115.7(3) . . ? C18 C17 C22 118.8(3) . . ? C18 C17 C23 119.9(3) . . ? C22 C17 C23 121.2(3) . . ? C30 C31 C26 121.3(3) . . ? C30 C31 H31 119.4 . . ? C26 C31 H31 119.4 . . ? O10 C34 O9 123.5(3) . . ? O10 C34 C30 121.0(3) . . ? O9 C34 C30 115.5(3) . . ? O1 C23 O2 125.1(3) . . ? O1 C23 C17 121.4(3) . . ? O2 C23 C17 113.4(3) . . ? C11 C12 N1 116.9(3) . . ? C11 C12 H12A 108.1 . . ? N1 C12 H12A 108.1 . . ? C11 C12 H12B 108.1 . . ? N1 C12 H12B 108.1 . . ? H12A C12 H12B 107.3 . . ? N1 C16 C15 115.1(3) . . ? N1 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? N1 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C12 C11 C10 110.8(3) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C7 C6 C5 114.1(3) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C1 C2 C3 113.2(5) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.8 . . ? C7 C8 N1 115.4(3) . . ? C7 C8 H8A 108.4 . . ? N1 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? N1 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C7 C8 110.7(3) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C14 C15 C16 112.4(3) . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? N1 C4 C3 116.1(3) . . ? N1 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? N1 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C10 C9 113.3(3) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C15 C14 C13 112.7(4) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C3 C2 108.5(3) . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O6 C25 O5 125.9(3) . . ? O6 C25 C21 117.1(3) . . ? O5 C25 C21 117.0(3) . . ? C25 O5 Zn1 132.48(19) . 3_457 ? C25 O6 Zn2 130.85(19) . 3_457 ? 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 Zn2 O7 C32 O8 7.0(4) 4_656 . . . ? Zn2 O7 C32 C26 -173.45(18) 4_656 . . . ? O8 C32 C26 C31 -173.9(3) . . . . ? O7 C32 C26 C31 6.5(4) . . . . ? O8 C32 C26 C27 6.7(4) . . . . ? O7 C32 C26 C27 -172.8(3) . . . . ? C31 C26 C27 C28 -0.1(4) . . . . ? C32 C26 C27 C28 179.3(3) . . . . ? C31 C30 C29 C28 0.2(4) . . . . ? C34 C30 C29 C28 -178.5(3) . . . . ? C26 C27 C28 C29 0.1(4) . . . . ? C26 C27 C28 C33 179.5(3) . . . . ? C30 C29 C28 C27 -0.2(4) . . . . ? C30 C29 C28 C33 -179.6(3) . . . . ? C27 C28 C33 O11 -175.5(3) . . . . ? C29 C28 C33 O11 4.0(4) . . . . ? C27 C28 C33 O12 3.8(4) . . . . ? C29 C28 C33 O12 -176.8(2) . . . . ? O11 C33 O12 Zn2 -11.1(4) . . . . ? C28 C33 O12 Zn2 169.72(18) . . . . ? O12 C33 O11 Zn3 -23.5(4) . . . . ? C28 C33 O11 Zn3 155.67(19) . . . . ? C33 O12 Zn2 O7 140.8(2) . . . 4_646 ? C33 O12 Zn2 O6 -92.4(2) . . . 3_557 ? C33 O12 Zn2 O13 25.9(2) . . . . ? C33 O11 Zn3 O9 -89.4(3) . . . 7_655 ? C33 O11 Zn3 O4 152.4(3) . . . . ? C33 O11 Zn3 O13 32.5(3) . . . . ? O9 Zn3 O4 C24 115.8(2) 7_655 . . . ? O13 Zn3 O4 C24 -17.6(2) . . . . ? O11 Zn3 O4 C24 -131.6(2) . . . . ? O2 Zn1 O13 Zn3 119.70(10) 5_657 . . . ? O5 Zn1 O13 Zn3 -104.76(10) 3_557 . . . ? O3 Zn1 O13 Zn3 6.71(11) . . . . ? O2 Zn1 O13 Zn2 -114.69(10) 5_657 . . . ? O5 Zn1 O13 Zn2 20.86(11) 3_557 . . . ? O3 Zn1 O13 Zn2 132.33(9) . . . . ? O9 Zn3 O13 Zn1 -132.11(9) 7_655 . . . ? O4 Zn3 O13 Zn1 -1.12(11) . . . . ? O11 Zn3 O13 Zn1 115.38(9) . . . . ? O9 Zn3 O13 Zn2 103.79(10) 7_655 . . . ? O4 Zn3 O13 Zn2 -125.22(9) . . . . ? O11 Zn3 O13 Zn2 -8.72(11) . . . . ? O7 Zn2 O13 Zn1 104.15(9) 4_646 . . . ? O6 Zn2 O13 Zn1 -18.72(11) 3_557 . . . ? O12 Zn2 O13 Zn1 -135.22(9) . . . . ? O7 Zn2 O13 Zn3 -130.15(9) 4_646 . . . ? O6 Zn2 O13 Zn3 106.98(10) 3_557 . . . ? O12 Zn2 O13 Zn3 -9.52(11) . . . . ? O2 Zn1 O3 C24 -125.4(3) 5_657 . . . ? O5 Zn1 O3 C24 114.2(3) 3_557 . . . ? O13 Zn1 O3 C24 1.4(3) . . . . ? C20 C21 C22 C17 1.2(4) . . . . ? C25 C21 C22 C17 -178.0(3) . . . . ? C18 C19 C20 C21 1.5(4) . . . . ? C24 C19 C20 C21 178.7(3) . . . . ? C22 C21 C20 C19 -2.7(4) . . . . ? C25 C21 C20 C19 176.4(3) . . . . ? C20 C19 C18 C17 1.3(4) . . . . ? C24 C19 C18 C17 -176.0(3) . . . . ? Zn3 O4 C24 O3 29.8(4) . . . . ? Zn3 O4 C24 C19 -149.27(19) . . . . ? Zn1 O3 C24 O4 -22.7(5) . . . . ? Zn1 O3 C24 C19 156.5(2) . . . . ? C18 C19 C24 O4 158.8(3) . . . . ? C20 C19 C24 O4 -18.4(4) . . . . ? C18 C19 C24 O3 -20.4(4) . . . . ? C20 C19 C24 O3 162.4(3) . . . . ? C19 C18 C17 C22 -2.8(4) . . . . ? C19 C18 C17 C23 174.6(3) . . . . ? C21 C22 C17 C18 1.5(4) . . . . ? C21 C22 C17 C23 -175.9(3) . . . . ? C29 C30 C31 C26 -0.2(4) . . . . ? C34 C30 C31 C26 178.5(3) . . . . ? C27 C26 C31 C30 0.1(4) . . . . ? C32 C26 C31 C30 -179.3(3) . . . . ? Zn3 O9 C34 O10 0.9(4) 7_665 . . . ? Zn3 O9 C34 C30 -179.00(19) 7_665 . . . ? C29 C30 C34 O10 -19.8(4) . . . . ? C31 C30 C34 O10 161.5(3) . . . . ? C29 C30 C34 O9 160.1(3) . . . . ? C31 C30 C34 O9 -18.6(4) . . . . ? Zn1 O2 C23 O1 16.4(5) 5_657 . . . ? Zn1 O2 C23 C17 -162.30(19) 5_657 . . . ? C18 C17 C23 O1 -175.2(3) . . . . ? C22 C17 C23 O1 2.2(5) . . . . ? C18 C17 C23 O2 3.6(4) . . . . ? C22 C17 C23 O2 -179.1(3) . . . . ? C16 N1 C12 C11 -55.6(4) . . . . ? C4 N1 C12 C11 -175.5(3) . . . . ? C8 N1 C12 C11 63.3(4) . . . . ? C4 N1 C16 C15 60.8(4) . . . . ? C8 N1 C16 C15 -177.9(3) . . . . ? C12 N1 C16 C15 -57.0(4) . . . . ? N1 C12 C11 C10 178.8(3) . . . . ? C16 N1 C8 C7 -173.3(3) . . . . ? C4 N1 C8 C7 -52.4(4) . . . . ? C12 N1 C8 C7 66.3(4) . . . . ? C5 C6 C7 C8 176.3(3) . . . . ? N1 C8 C7 C6 179.0(3) . . . . ? N1 C16 C15 C14 -172.7(4) . . . . ? C16 N1 C4 C3 62.5(4) . . . . ? C8 N1 C4 C3 -56.7(4) . . . . ? C12 N1 C4 C3 -177.8(3) . . . . ? C12 C11 C10 C9 -176.3(3) . . . . ? C16 C15 C14 C13 173.2(4) . . . . ? N1 C4 C3 C2 174.3(4) . . . . ? C1 C2 C3 C4 -179.1(5) . . . . ? C20 C21 C25 O6 -166.4(3) . . . . ? C22 C21 C25 O6 12.8(4) . . . . ? C20 C21 C25 O5 13.5(4) . . . . ? C22 C21 C25 O5 -167.3(3) . . . . ? O6 C25 O5 Zn1 8.5(5) . . . 3_457 ? C21 C25 O5 Zn1 -171.36(18) . . . 3_457 ? O5 C25 O6 Zn2 -3.7(5) . . . 3_457 ? C21 C25 O6 Zn2 176.18(18) . . . 3_457 ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.445 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.075 data_5 _database_code_depnum_ccdc_archive 'CCDC 771707' #TrackingRef '- CIF 1-5-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 N3 O7 Zn2' _chemical_formula_weight 487.01 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 19.5062(4) _cell_length_b 12.3730(6) _cell_length_c 15.0076(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.7170(10) _cell_angle_gamma 90.00 _cell_volume 3316.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 164 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 23.55 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.951 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 2.942 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6346 _exptl_absorpt_correction_T_max 0.7379 _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8302 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2927 _reflns_number_gt 2431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _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. All absorption corrections were performed by using the SADABS program. The crystal structure was solved by direct methods and refined with full-matrix least-squares 'SHELXTL-97' with atomic coordinates and anisotropic thermal parameters for all nonhydrogen atoms. The hydrogen atoms of aromatic rings were included in the structure factor calculation at idealized positions by using a riding model. ; _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^)+(0.0329P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2927 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0625 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.002 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 Zn2 Zn 0.898292(16) 0.47377(2) -0.16286(2) 0.02444(10) Uani 1 1 d . . . O4 O 0.90966(11) 0.35779(16) -0.29450(14) 0.0381(5) Uani 1 1 d . . . O3 O 0.84649(11) 0.57557(16) -0.10625(12) 0.0333(5) Uani 1 1 d . . . C12 C 0.83565(13) 0.5717(2) -0.02942(17) 0.0215(5) Uani 1 1 d . . . O2 O 0.85669(11) 0.49791(15) 0.03272(13) 0.0357(5) Uani 1 1 d . . . Zn1 Zn 0.937944(17) 0.38098(3) 0.06134(2) 0.02652(11) Uani 1 1 d . . . N1 N 0.88262(13) 0.26474(19) 0.10610(16) 0.0332(6) Uani 1 1 d . . . O5 O 0.81094(10) 0.43637(17) -0.28885(13) 0.0360(5) Uani 1 1 d . . . O7 O 1.01935(12) 0.4451(2) 0.16589(15) 0.0572(7) Uani 1 1 d . . . O6 O 0.92767(15) 0.35770(19) -0.06949(15) 0.0451(6) Uani 1 1 d . . . C15 C 0.79169(13) 0.3157(2) -0.42072(16) 0.0203(5) Uani 1 1 d . . . C6 C 0.99119(17) 0.0238(2) 0.1221(2) 0.0348(7) Uani 1 1 d . . . C11 C 0.91026(16) 0.1652(2) 0.11536(19) 0.0333(7) Uani 1 1 d . . . C10 C 0.98016(16) 0.1347(2) 0.1083(2) 0.0351(7) Uani 1 1 d . . . N2 N 1.02570(15) 0.2047(2) 0.09225(18) 0.0454(7) Uani 1 1 d . . . C5 C 0.92633(17) -0.0200(2) 0.1373(2) 0.0360(7) Uani 1 1 d . . . C4 C 0.87851(16) 0.0730(2) 0.1364(2) 0.0361(7) Uani 1 1 d . . . C1 C 0.81855(17) 0.2760(3) 0.1200(2) 0.0414(7) Uani 1 1 d . . . H1 H 0.7972 0.3442 0.1144 0.050 Uiso 1 1 calc R . . C3 C 0.81328(17) 0.0857(3) 0.1501(2) 0.0443(8) Uani 1 1 d . . . H3 H 0.7896 0.0270 0.1643 0.053 Uiso 1 1 calc R . . C2 C 0.78418(18) 0.1889(3) 0.1422(2) 0.0461(8) Uani 1 1 d . . . H2 H 0.7406 0.1998 0.1520 0.055 Uiso 1 1 calc R . . C7 C 1.05656(18) -0.0196(3) 0.1228(2) 0.0421(8) Uani 1 1 d . . . H7 H 1.0671 -0.0930 0.1325 0.050 Uiso 1 1 calc R . . C8 C 1.10575(19) 0.0520(3) 0.1081(2) 0.0472(8) Uani 1 1 d . . . H8 H 1.1509 0.0270 0.1087 0.057 Uiso 1 1 calc R . . C9 C 1.08795(19) 0.1600(3) 0.0926(2) 0.0519(9) Uani 1 1 d . . . H9 H 1.1219 0.2051 0.0816 0.062 Uiso 1 1 calc R . . N3 N 0.90871(14) -0.1169(2) 0.14973(18) 0.0413(6) Uani 1 1 d . . . O1 O 0.95852(12) -0.19150(17) 0.14316(15) 0.0484(6) Uani 1 1 d . . . H1O H 0.9454 -0.2523 0.1514 0.073 Uiso 1 1 calc R . . C16 C 0.84110(15) 0.3761(2) -0.32934(18) 0.0249(6) Uani 1 1 d . . . C13 C 0.79193(13) 0.6639(2) -0.01255(17) 0.0200(5) Uani 1 1 d . . . C14 C 0.74969(14) 0.7303(2) -0.08975(17) 0.0224(6) Uani 1 1 d . . . H14 H 0.7494 0.7166 -0.1509 0.027 Uiso 1 1 calc R . . H6O H 0.952(2) 0.318(3) -0.071(3) 0.052(13) Uiso 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 Zn2 0.02414(18) 0.03016(19) 0.01790(17) -0.00492(12) 0.00730(13) -0.00207(13) O4 0.0260(11) 0.0371(12) 0.0358(11) -0.0148(9) -0.0036(9) 0.0025(9) O3 0.0455(12) 0.0347(11) 0.0256(10) 0.0016(9) 0.0206(9) 0.0117(9) C12 0.0198(13) 0.0240(14) 0.0191(13) -0.0020(11) 0.0064(11) -0.0010(11) O2 0.0477(12) 0.0330(11) 0.0327(11) 0.0101(9) 0.0228(10) 0.0167(10) Zn1 0.02961(19) 0.02718(19) 0.02150(17) 0.00144(12) 0.00896(14) -0.00211(13) N1 0.0324(13) 0.0327(14) 0.0301(13) 0.0037(10) 0.0081(11) -0.0066(11) O5 0.0312(11) 0.0511(13) 0.0258(10) -0.0170(10) 0.0117(9) -0.0040(10) O7 0.0506(14) 0.0905(19) 0.0382(12) -0.0312(12) 0.0259(11) -0.0445(13) O6 0.0686(17) 0.0427(15) 0.0281(12) 0.0071(10) 0.0236(12) 0.0260(13) C15 0.0181(13) 0.0238(14) 0.0170(12) -0.0049(10) 0.0048(10) -0.0009(11) C6 0.0383(17) 0.0337(17) 0.0261(15) 0.0026(12) 0.0062(13) -0.0084(14) C11 0.0362(16) 0.0319(17) 0.0251(15) 0.0031(12) 0.0053(13) -0.0084(14) C10 0.0363(17) 0.0347(18) 0.0279(15) 0.0042(12) 0.0062(13) -0.0107(13) N2 0.0459(16) 0.0411(17) 0.0453(16) 0.0070(12) 0.0144(13) -0.0172(13) C5 0.0390(17) 0.0321(17) 0.0296(15) 0.0049(13) 0.0062(13) -0.0108(14) C4 0.0359(17) 0.0357(17) 0.0296(15) 0.0031(13) 0.0057(13) -0.0129(14) C1 0.0380(18) 0.045(2) 0.0408(17) 0.0043(15) 0.0152(15) -0.0001(15) C3 0.0393(19) 0.050(2) 0.0368(18) 0.0057(15) 0.0084(15) -0.0171(16) C2 0.0370(18) 0.057(2) 0.0466(19) 0.0052(16) 0.0194(15) -0.0059(16) C7 0.0456(19) 0.0427(19) 0.0341(17) 0.0015(14) 0.0119(15) -0.0040(15) C8 0.0401(18) 0.056(2) 0.0435(19) 0.0011(16) 0.0145(16) -0.0091(16) C9 0.042(2) 0.063(2) 0.051(2) 0.0084(18) 0.0182(17) -0.0172(18) N3 0.0422(15) 0.0340(15) 0.0418(15) 0.0057(12) 0.0106(13) -0.0058(13) O1 0.0534(14) 0.0360(13) 0.0537(13) 0.0071(11) 0.0195(12) -0.0082(11) C16 0.0316(16) 0.0221(14) 0.0212(13) -0.0027(11) 0.0106(12) -0.0069(12) C13 0.0185(13) 0.0231(13) 0.0176(12) 0.0010(10) 0.0065(10) 0.0006(11) C14 0.0237(13) 0.0298(15) 0.0151(12) 0.0005(11) 0.0094(10) 0.0028(11) _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 Zn2 O7 1.910(2) 5_765 ? Zn2 O6 1.926(2) . ? Zn2 O3 2.0049(17) . ? Zn2 O5 2.0250(18) . ? Zn2 C16 2.589(3) . ? O4 C16 1.245(3) . ? O3 C12 1.254(3) . ? C12 O2 1.251(3) . ? C12 C13 1.505(3) . ? O2 Zn1 2.0596(18) . ? Zn1 O7 1.900(2) . ? Zn1 O6 1.914(2) . ? Zn1 N1 2.066(2) . ? N1 C11 1.329(4) . ? N1 C1 1.354(4) . ? O5 C16 1.249(3) . ? O7 Zn2 1.910(2) 5_765 ? O6 H6O 0.69(3) . ? C15 C14 1.377(3) 4_644 ? C15 C13 1.403(3) 6_565 ? C15 C16 1.518(3) . ? C6 C7 1.380(4) . ? C6 C10 1.391(4) . ? C6 C5 1.476(4) . ? C11 C4 1.394(4) . ? C11 C10 1.459(4) . ? C10 N2 1.330(4) . ? N2 C9 1.332(4) . ? C5 N3 1.280(3) . ? C5 C4 1.478(4) . ? C4 C3 1.377(4) . ? C1 C2 1.378(4) . ? C1 H1 0.9300 . ? C3 C2 1.383(5) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C7 C8 1.387(4) . ? C7 H7 0.9300 . ? C8 C9 1.376(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? N3 O1 1.373(3) . ? O1 H1O 0.8200 . ? C13 C14 1.389(3) . ? C13 C15 1.403(3) 6_566 ? C14 C15 1.377(3) 4_654 ? C14 H14 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 Zn2 O6 113.73(11) 5_765 . ? O7 Zn2 O3 104.59(9) 5_765 . ? O6 Zn2 O3 102.32(9) . . ? O7 Zn2 O5 119.84(9) 5_765 . ? O6 Zn2 O5 113.66(10) . . ? O3 Zn2 O5 99.26(8) . . ? O7 Zn2 C16 105.21(8) 5_765 . ? O6 Zn2 C16 103.92(9) . . ? O3 Zn2 C16 127.38(8) . . ? O5 Zn2 C16 28.15(8) . . ? C12 O3 Zn2 131.76(17) . . ? O2 C12 O3 125.9(2) . . ? O2 C12 C13 117.8(2) . . ? O3 C12 C13 116.3(2) . . ? C12 O2 Zn1 131.50(17) . . ? O7 Zn1 O6 128.19(10) . . ? O7 Zn1 O2 101.33(10) . . ? O6 Zn1 O2 97.90(9) . . ? O7 Zn1 N1 113.24(9) . . ? O6 Zn1 N1 112.09(10) . . ? O2 Zn1 N1 95.62(9) . . ? C11 N1 C1 116.1(2) . . ? C11 N1 Zn1 115.85(19) . . ? C1 N1 Zn1 127.8(2) . . ? C16 O5 Zn2 101.93(17) . . ? Zn1 O7 Zn2 129.15(11) . 5_765 ? Zn1 O6 Zn2 120.80(12) . . ? Zn1 O6 H6O 111(3) . . ? Zn2 O6 H6O 121(3) . . ? C14 C15 C13 118.9(2) 4_644 6_565 ? C14 C15 C16 117.6(2) 4_644 . ? C13 C15 C16 123.2(2) 6_565 . ? C7 C6 C10 118.2(3) . . ? C7 C6 C5 134.7(3) . . ? C10 C6 C5 107.1(3) . . ? N1 C11 C4 125.7(3) . . ? N1 C11 C10 125.7(3) . . ? C4 C11 C10 108.5(3) . . ? N2 C10 C6 126.4(3) . . ? N2 C10 C11 123.8(3) . . ? C6 C10 C11 109.8(2) . . ? C10 N2 C9 113.8(3) . . ? N3 C5 C6 131.5(3) . . ? N3 C5 C4 121.6(3) . . ? C6 C5 C4 106.8(2) . . ? C3 C4 C11 117.5(3) . . ? C3 C4 C5 134.9(3) . . ? C11 C4 C5 107.7(3) . . ? N1 C1 C2 121.7(3) . . ? N1 C1 H1 119.2 . . ? C2 C1 H1 119.1 . . ? C4 C3 C2 117.7(3) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C1 C2 C3 121.3(3) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C6 C7 C8 116.5(3) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? N2 C9 C8 124.8(3) . . ? N2 C9 H9 117.6 . . ? C8 C9 H9 117.6 . . ? C5 N3 O1 112.3(3) . . ? N3 O1 H1O 109.5 . . ? O4 C16 O5 122.8(2) . . ? O4 C16 C15 118.3(2) . . ? O5 C16 C15 118.8(2) . . ? O4 C16 Zn2 72.95(14) . . ? O5 C16 Zn2 49.92(12) . . ? C15 C16 Zn2 166.39(18) . . ? C14 C13 C15 118.5(2) . 6_566 ? C14 C13 C12 119.6(2) . . ? C15 C13 C12 121.8(2) 6_566 . ? C15 C14 C13 122.5(2) 4_654 . ? C15 C14 H14 118.7 4_654 . ? C13 C14 H14 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 Zn2 O3 C12 -117.1(2) 5_765 . . . ? O6 Zn2 O3 C12 1.8(3) . . . . ? O5 Zn2 O3 C12 118.6(2) . . . . ? C16 Zn2 O3 C12 120.3(2) . . . . ? Zn2 O3 C12 O2 0.1(4) . . . . ? Zn2 O3 C12 C13 -178.55(16) . . . . ? O3 C12 O2 Zn1 19.7(4) . . . . ? C13 C12 O2 Zn1 -161.63(17) . . . . ? C12 O2 Zn1 O7 97.5(2) . . . . ? C12 O2 Zn1 O6 -34.2(3) . . . . ? C12 O2 Zn1 N1 -147.5(2) . . . . ? O7 Zn1 N1 C11 -87.2(2) . . . . ? O6 Zn1 N1 C11 67.0(2) . . . . ? O2 Zn1 N1 C11 167.92(19) . . . . ? O7 Zn1 N1 C1 98.3(2) . . . . ? O6 Zn1 N1 C1 -107.5(2) . . . . ? O2 Zn1 N1 C1 -6.6(2) . . . . ? O7 Zn2 O5 C16 64.5(2) 5_765 . . . ? O6 Zn2 O5 C16 -74.81(19) . . . . ? O3 Zn2 O5 C16 177.28(17) . . . . ? O6 Zn1 O7 Zn2 13.2(3) . . . 5_765 ? O2 Zn1 O7 Zn2 -96.47(18) . . . 5_765 ? N1 Zn1 O7 Zn2 162.29(16) . . . 5_765 ? O7 Zn1 O6 Zn2 -79.62(19) . . . . ? O2 Zn1 O6 Zn2 31.58(16) . . . . ? N1 Zn1 O6 Zn2 130.97(14) . . . . ? O7 Zn2 O6 Zn1 89.80(16) 5_765 . . . ? O3 Zn2 O6 Zn1 -22.39(16) . . . . ? O5 Zn2 O6 Zn1 -128.38(13) . . . . ? C16 Zn2 O6 Zn1 -156.36(14) . . . . ? C1 N1 C11 C4 1.0(4) . . . . ? Zn1 N1 C11 C4 -174.2(2) . . . . ? C1 N1 C11 C10 -176.9(3) . . . . ? Zn1 N1 C11 C10 7.9(3) . . . . ? C7 C6 C10 N2 2.4(4) . . . . ? C5 C6 C10 N2 180.0(3) . . . . ? C7 C6 C10 C11 -176.9(3) . . . . ? C5 C6 C10 C11 0.7(3) . . . . ? N1 C11 C10 N2 0.6(4) . . . . ? C4 C11 C10 N2 -177.6(3) . . . . ? N1 C11 C10 C6 179.8(3) . . . . ? C4 C11 C10 C6 1.7(3) . . . . ? C6 C10 N2 C9 -1.8(4) . . . . ? C11 C10 N2 C9 177.3(3) . . . . ? C7 C6 C5 N3 -5.6(6) . . . . ? C10 C6 C5 N3 177.3(3) . . . . ? C7 C6 C5 C4 174.3(3) . . . . ? C10 C6 C5 C4 -2.7(3) . . . . ? N1 C11 C4 C3 -0.9(4) . . . . ? C10 C11 C4 C3 177.3(3) . . . . ? N1 C11 C4 C5 178.5(3) . . . . ? C10 C11 C4 C5 -3.3(3) . . . . ? N3 C5 C4 C3 3.0(5) . . . . ? C6 C5 C4 C3 -177.0(3) . . . . ? N3 C5 C4 C11 -176.3(3) . . . . ? C6 C5 C4 C11 3.7(3) . . . . ? C11 N1 C1 C2 -0.1(4) . . . . ? Zn1 N1 C1 C2 174.4(2) . . . . ? C11 C4 C3 C2 -0.1(4) . . . . ? C5 C4 C3 C2 -179.3(3) . . . . ? N1 C1 C2 C3 -0.8(5) . . . . ? C4 C3 C2 C1 0.9(4) . . . . ? C10 C6 C7 C8 -0.9(4) . . . . ? C5 C6 C7 C8 -177.7(3) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C10 N2 C9 C8 -0.1(5) . . . . ? C7 C8 C9 N2 1.4(5) . . . . ? C6 C5 N3 O1 -3.2(4) . . . . ? C4 C5 N3 O1 176.9(2) . . . . ? Zn2 O5 C16 O4 -4.4(3) . . . . ? Zn2 O5 C16 C15 170.78(18) . . . . ? C14 C15 C16 O4 102.8(3) 4_644 . . . ? C13 C15 C16 O4 -70.9(3) 6_565 . . . ? C14 C15 C16 O5 -72.6(3) 4_644 . . . ? C13 C15 C16 O5 113.8(3) 6_565 . . . ? C14 C15 C16 Zn2 -41.2(9) 4_644 . . . ? C13 C15 C16 Zn2 145.2(7) 6_565 . . . ? O7 Zn2 C16 O4 50.34(18) 5_765 . . . ? O6 Zn2 C16 O4 -69.46(17) . . . . ? O3 Zn2 C16 O4 172.76(14) . . . . ? O5 Zn2 C16 O4 176.1(3) . . . . ? O7 Zn2 C16 O5 -125.80(19) 5_765 . . . ? O6 Zn2 C16 O5 114.40(18) . . . . ? O3 Zn2 C16 O5 -3.4(2) . . . . ? O7 Zn2 C16 C15 -162.5(8) 5_765 . . . ? O6 Zn2 C16 C15 77.7(8) . . . . ? O3 Zn2 C16 C15 -40.0(8) . . . . ? O5 Zn2 C16 C15 -36.7(7) . . . . ? O2 C12 C13 C14 -161.7(2) . . . . ? O3 C12 C13 C14 17.1(3) . . . . ? O2 C12 C13 C15 17.4(4) . . . 6_566 ? O3 C12 C13 C15 -163.8(2) . . . 6_566 ? C15 C13 C14 C15 0.6(4) 6_566 . . 4_654 ? C12 C13 C14 C15 179.8(2) . . . 4_654 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.410 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.073