data_ZNM _audit_creation_method SHELXL-97 _chemical_name_systematic '?' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 N2 O11 Zn2.50' _chemical_formula_weight 630.74 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 ? _symmetry_space_group_name_H-M ? 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 17.0298(14) _cell_length_b 13.9683(11) _cell_length_c 19.3375(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.635(2) _cell_angle_gamma 90.00 _cell_volume 4505.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.860 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 2.716 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6990 _exptl_absorpt_correction_T_max 0.8120 _exptl_absorpt_process_details ? _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 ? _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 9459 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4402 _reflns_number_gt 3646 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0620P)^2^+14.8855P] 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 4402 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 0.30407(5) 0.2500 0.01289(18) Uani 1 2 d S . . Zn2 Zn 0.08534(3) 0.41922(4) 0.39881(3) 0.01767(16) Uani 1 1 d . . . Zn3 Zn -0.06660(3) 0.26087(4) 0.40179(3) 0.01898(16) Uani 1 1 d . . . O1 O -0.1581(2) 0.2304(3) 0.32281(17) 0.0254(8) Uani 1 1 d . . . O2 O -0.09070(19) 0.2013(2) 0.23668(17) 0.0199(7) Uani 1 1 d . . . O3 O -0.2065(2) 0.3096(2) 0.11893(19) 0.0296(9) Uani 1 1 d . . . O4 O -0.1810(2) 0.1799(3) 0.0605(2) 0.0307(9) Uani 1 1 d . . . O5 O -0.3699(2) 0.2091(3) 0.02471(19) 0.0304(9) Uani 1 1 d . . . O6 O -0.3588(2) 0.0565(2) -0.00448(17) 0.0253(8) Uani 1 1 d . . . O7 O -0.4016(2) -0.1017(2) 0.08894(18) 0.0264(8) Uani 1 1 d . . . O8 O -0.4912(2) 0.0080(2) 0.1087(2) 0.0295(8) Uani 1 1 d . . . O9 O -0.4178(2) -0.0934(2) 0.23927(18) 0.0240(8) Uani 1 1 d . . . O10 O -0.3625(2) -0.0093(2) 0.33458(16) 0.0225(7) Uani 1 1 d . . . O11 O 0.0287(2) 0.2991(3) 0.36387(17) 0.0145(7) Uani 1 1 d . . . N1 N -0.0467(3) 0.1050(3) 0.4095(2) 0.0328(11) Uani 1 1 d . . . N2 N -0.1092(3) 0.2239(3) 0.4906(2) 0.0314(11) Uani 1 1 d . . . C1 C -0.2256(3) 0.1468(3) 0.2231(2) 0.0178(10) Uani 1 1 d . . . C2 C -0.2521(3) 0.1561(3) 0.1502(2) 0.0176(10) Uani 1 1 d . . . C3 C -0.3164(3) 0.1026(3) 0.1152(2) 0.0165(10) Uani 1 1 d . . . C4 C -0.3538(3) 0.0371(3) 0.1528(2) 0.0155(9) Uani 1 1 d . . . C5 C -0.3301(3) 0.0323(3) 0.2262(2) 0.0162(10) Uani 1 1 d . . . C6 C -0.2664(3) 0.0869(3) 0.2601(2) 0.0204(10) Uani 1 1 d . . . H6 H -0.2506 0.0832 0.3089 0.024 Uiso 1 1 calc R . . C7 C -0.1523(3) 0.1980(3) 0.2634(2) 0.0169(10) Uani 1 1 d . . . C8 C -0.2118(3) 0.2245(3) 0.1088(2) 0.0204(10) Uani 1 1 d . . . C9 C -0.3508(3) 0.1242(3) 0.0390(2) 0.0185(10) Uani 1 1 d . . . C10 C -0.4209(3) -0.0244(3) 0.1140(2) 0.0187(10) Uani 1 1 d . . . C11 C -0.3738(3) -0.0295(3) 0.2700(2) 0.0161(10) Uani 1 1 d . . . C12 C -0.0154(4) 0.0491(4) 0.3662(3) 0.0433(15) Uani 1 1 d . . . H12 H 0.0193 0.0764 0.3403 0.052 Uiso 1 1 calc R . . C13 C -0.0318(5) -0.0462(5) 0.3582(4) 0.067(2) Uani 1 1 d . . . H13 H -0.0081 -0.0834 0.3282 0.081 Uiso 1 1 calc R . . C14 C -0.0850(7) -0.0865(5) 0.3961(5) 0.083(3) Uani 1 1 d . . . H14 H -0.0985 -0.1510 0.3909 0.100 Uiso 1 1 calc R . . C15 C -0.1173(5) -0.0296(5) 0.4411(5) 0.069(2) Uani 1 1 d . . . H15 H -0.1528 -0.0552 0.4670 0.083 Uiso 1 1 calc R . . C16 C -0.0967(4) 0.0657(4) 0.4476(3) 0.0366(14) Uani 1 1 d . . . C17 C -0.1276(4) 0.1311(4) 0.4963(3) 0.0384(14) Uani 1 1 d . . . C18 C -0.1697(5) 0.1014(5) 0.5457(4) 0.060(2) Uani 1 1 d . . . H18 H -0.1827 0.0371 0.5485 0.073 Uiso 1 1 calc R . . C19 C -0.1925(5) 0.1661(7) 0.5908(4) 0.077(3) Uani 1 1 d . . . H19 H -0.2222 0.1465 0.6237 0.092 Uiso 1 1 calc R . . C20 C -0.1711(6) 0.2600(6) 0.5868(4) 0.072(3) Uani 1 1 d . . . H20 H -0.1843 0.3049 0.6182 0.086 Uiso 1 1 calc R . . C21 C -0.1299(4) 0.2871(5) 0.5357(3) 0.0498(17) Uani 1 1 d . . . H21 H -0.1160 0.3511 0.5324 0.060 Uiso 1 1 calc R . . H23 H 0.044(3) 0.257(4) 0.359(3) 0.019(17) Uiso 1 1 d . . . H4 H -0.159(4) 0.220(5) 0.036(4) 0.05(2) 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 Zn1 0.0114(4) 0.0143(4) 0.0131(4) 0.000 0.0029(3) 0.000 Zn2 0.0191(3) 0.0214(3) 0.0113(3) 0.0017(2) 0.0001(2) -0.0059(2) Zn3 0.0207(3) 0.0205(3) 0.0162(3) -0.0003(2) 0.0046(2) -0.0038(2) O1 0.0217(19) 0.040(2) 0.0150(18) -0.0088(15) 0.0047(15) -0.0117(16) O2 0.0199(18) 0.0205(17) 0.0192(17) -0.0039(13) 0.0038(14) -0.0104(14) O3 0.037(2) 0.0233(19) 0.030(2) 0.0014(15) 0.0109(18) -0.0105(16) O4 0.046(2) 0.026(2) 0.027(2) -0.0004(16) 0.0216(19) -0.0061(17) O5 0.039(2) 0.031(2) 0.0231(19) 0.0090(16) 0.0112(17) 0.0059(17) O6 0.034(2) 0.0267(19) 0.0118(17) 0.0007(14) -0.0028(15) -0.0079(16) O7 0.035(2) 0.0228(18) 0.0233(19) -0.0042(15) 0.0100(16) -0.0089(16) O8 0.0198(19) 0.030(2) 0.037(2) 0.0048(16) 0.0014(16) -0.0042(16) O9 0.0238(19) 0.0261(19) 0.0211(18) 0.0019(14) 0.0023(15) -0.0135(15) O10 0.0279(19) 0.0274(18) 0.0131(17) 0.0018(14) 0.0060(14) -0.0088(15) O11 0.0146(17) 0.0124(17) 0.0167(17) -0.0021(14) 0.0034(13) 0.0012(14) N1 0.043(3) 0.025(2) 0.033(3) 0.005(2) 0.013(2) 0.000(2) N2 0.037(3) 0.033(3) 0.026(2) 0.005(2) 0.009(2) 0.003(2) C1 0.020(2) 0.021(2) 0.014(2) -0.0020(18) 0.0050(19) -0.008(2) C2 0.017(2) 0.021(2) 0.014(2) 0.0016(19) 0.0022(19) -0.0045(19) C3 0.018(2) 0.018(2) 0.014(2) -0.0003(18) 0.0044(19) -0.0030(19) C4 0.014(2) 0.016(2) 0.016(2) 0.0013(18) -0.0002(18) -0.0024(18) C5 0.015(2) 0.021(2) 0.013(2) 0.0027(18) 0.0040(18) -0.0016(19) C6 0.021(3) 0.028(3) 0.011(2) -0.0024(19) -0.0006(19) -0.006(2) C7 0.016(2) 0.018(2) 0.015(2) 0.0043(18) -0.0008(19) -0.0030(19) C8 0.021(3) 0.025(3) 0.014(2) 0.0032(19) 0.002(2) -0.009(2) C9 0.016(2) 0.024(3) 0.015(2) 0.004(2) 0.0047(19) -0.009(2) C10 0.021(3) 0.023(2) 0.010(2) 0.0024(19) 0.0001(19) -0.007(2) C11 0.010(2) 0.023(2) 0.016(2) 0.0055(19) 0.0044(18) -0.0002(19) C12 0.053(4) 0.033(3) 0.046(4) 0.006(3) 0.017(3) -0.001(3) C13 0.105(7) 0.032(4) 0.070(5) -0.004(4) 0.030(5) 0.013(4) C14 0.147(9) 0.025(4) 0.083(7) 0.001(4) 0.033(6) -0.015(5) C15 0.099(7) 0.034(4) 0.081(6) 0.008(4) 0.036(5) -0.020(4) C16 0.044(4) 0.028(3) 0.037(3) 0.013(2) 0.006(3) -0.002(3) C17 0.037(3) 0.042(3) 0.037(3) 0.014(3) 0.010(3) -0.004(3) C18 0.072(5) 0.059(4) 0.061(5) 0.024(4) 0.038(4) -0.003(4) C19 0.081(6) 0.101(7) 0.065(5) 0.041(5) 0.054(5) 0.018(5) C20 0.098(7) 0.087(6) 0.041(4) 0.007(4) 0.042(5) 0.021(5) C21 0.067(5) 0.056(4) 0.032(3) 0.002(3) 0.023(3) 0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O9 2.042(3) 3 ? Zn1 O9 2.042(3) 4_455 ? Zn1 O2 2.086(3) . ? Zn1 O2 2.086(3) 2 ? Zn1 O11 2.158(3) 2 ? Zn1 O11 2.158(3) . ? Zn2 O10 1.943(3) 3 ? Zn2 O6 1.949(3) 8_556 ? Zn2 O11 1.984(3) . ? Zn2 O8 2.008(3) 4_455 ? Zn3 O11 1.985(3) . ? Zn3 O1 1.995(3) . ? Zn3 O7 2.013(3) 4_455 ? Zn3 N2 2.061(4) . ? Zn3 N1 2.203(4) . ? O1 C7 1.256(6) . ? O2 C7 1.261(5) . ? O3 C8 1.205(6) . ? O4 C8 1.315(6) . ? O4 H4 0.87(7) . ? O5 C9 1.246(6) . ? O6 C9 1.254(6) . ? O6 Zn2 1.949(3) 8_455 ? O7 C10 1.254(6) . ? O7 Zn3 2.013(3) 4_445 ? O8 C10 1.265(6) . ? O8 Zn2 2.008(3) 4_445 ? O9 C11 1.237(5) . ? O9 Zn1 2.042(3) 3_445 ? O10 C11 1.257(5) . ? O10 Zn2 1.943(3) 3_445 ? O11 H23 0.66(5) . ? N1 C12 1.333(7) . ? N1 C16 1.348(7) . ? N2 C21 1.337(8) . ? N2 C17 1.342(7) . ? C1 C6 1.376(6) . ? C1 C2 1.397(6) . ? C1 C7 1.512(6) . ? C2 C3 1.384(6) . ? C2 C8 1.499(6) . ? C3 C4 1.401(6) . ? C3 C9 1.502(6) . ? C4 C5 1.397(6) . ? C4 C10 1.503(6) . ? C5 C6 1.379(6) . ? C5 C11 1.507(6) . ? C6 H6 0.9300 . ? C12 C13 1.363(9) . ? C12 H12 0.9300 . ? C13 C14 1.393(11) . ? C13 H13 0.9300 . ? C14 C15 1.373(11) . ? C14 H14 0.9300 . ? C15 C16 1.376(8) . ? C15 H15 0.9300 . ? C16 C17 1.484(9) . ? C17 C18 1.368(8) . ? C18 C19 1.366(11) . ? C18 H18 0.9300 . ? C19 C20 1.368(11) . ? C19 H19 0.9300 . ? C20 C21 1.376(9) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Zn1 O9 90.9(2) 3 4_455 ? O9 Zn1 O2 167.31(13) 3 . ? O9 Zn1 O2 89.40(13) 4_455 . ? O9 Zn1 O2 89.40(13) 3 2 ? O9 Zn1 O2 167.31(13) 4_455 2 ? O2 Zn1 O2 93.06(19) . 2 ? O9 Zn1 O11 86.44(13) 3 2 ? O9 Zn1 O11 96.14(13) 4_455 2 ? O2 Zn1 O11 80.91(13) . 2 ? O2 Zn1 O11 96.54(12) 2 2 ? O9 Zn1 O11 96.14(13) 3 . ? O9 Zn1 O11 86.44(13) 4_455 . ? O2 Zn1 O11 96.54(12) . . ? O2 Zn1 O11 80.91(13) 2 . ? O11 Zn1 O11 176.33(19) 2 . ? O10 Zn2 O6 109.06(14) 3 8_556 ? O10 Zn2 O11 118.05(14) 3 . ? O6 Zn2 O11 125.67(14) 8_556 . ? O10 Zn2 O8 95.59(15) 3 4_455 ? O6 Zn2 O8 100.93(14) 8_556 4_455 ? O11 Zn2 O8 99.90(14) . 4_455 ? O11 Zn3 O1 110.21(13) . . ? O11 Zn3 O7 91.77(15) . 4_455 ? O1 Zn3 O7 95.13(15) . 4_455 ? O11 Zn3 N2 145.83(17) . . ? O1 Zn3 N2 103.43(17) . . ? O7 Zn3 N2 91.08(16) 4_455 . ? O11 Zn3 N1 99.52(16) . . ? O1 Zn3 N1 85.78(17) . . ? O7 Zn3 N1 167.62(15) 4_455 . ? N2 Zn3 N1 76.74(17) . . ? C7 O1 Zn3 125.7(3) . . ? C7 O2 Zn1 129.2(3) . . ? C8 O4 H4 111(4) . . ? C9 O6 Zn2 118.6(3) . 8_455 ? C10 O7 Zn3 133.7(3) . 4_445 ? C10 O8 Zn2 120.9(3) . 4_445 ? C11 O9 Zn1 144.9(3) . 3_445 ? C11 O10 Zn2 121.4(3) . 3_445 ? Zn2 O11 Zn3 118.63(17) . . ? Zn2 O11 Zn1 108.36(15) . . ? Zn3 O11 Zn1 110.57(15) . . ? Zn2 O11 H23 129(5) . . ? Zn3 O11 H23 100(5) . . ? Zn1 O11 H23 84(5) . . ? C12 N1 C16 118.7(5) . . ? C12 N1 Zn3 127.7(4) . . ? C16 N1 Zn3 109.6(4) . . ? C21 N2 C17 119.1(5) . . ? C21 N2 Zn3 124.1(4) . . ? C17 N2 Zn3 116.0(4) . . ? C6 C1 C2 119.2(4) . . ? C6 C1 C7 118.0(4) . . ? C2 C1 C7 122.8(4) . . ? C3 C2 C1 120.3(4) . . ? C3 C2 C8 119.0(4) . . ? C1 C2 C8 120.6(4) . . ? C2 C3 C4 119.8(4) . . ? C2 C3 C9 119.0(4) . . ? C4 C3 C9 120.8(4) . . ? C5 C4 C3 119.3(4) . . ? C5 C4 C10 121.1(4) . . ? C3 C4 C10 119.6(4) . . ? C6 C5 C4 119.7(4) . . ? C6 C5 C11 118.8(4) . . ? C4 C5 C11 121.5(4) . . ? C1 C6 C5 121.4(4) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O1 C7 O2 125.9(4) . . ? O1 C7 C1 115.7(4) . . ? O2 C7 C1 118.4(4) . . ? O3 C8 O4 123.7(4) . . ? O3 C8 C2 124.6(4) . . ? O4 C8 C2 111.6(4) . . ? O5 C9 O6 125.5(4) . . ? O5 C9 C3 116.2(4) . . ? O6 C9 C3 118.4(4) . . ? O7 C10 O8 126.5(4) . . ? O7 C10 C4 116.9(4) . . ? O8 C10 C4 116.6(4) . . ? O9 C11 O10 126.6(4) . . ? O9 C11 C5 117.6(4) . . ? O10 C11 C5 115.8(4) . . ? N1 C12 C13 123.0(6) . . ? N1 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 118.4(7) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C15 C14 C13 119.1(7) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 119.3(7) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N1 C16 C15 121.5(6) . . ? N1 C16 C17 116.1(5) . . ? C15 C16 C17 122.4(6) . . ? N2 C17 C18 120.9(6) . . ? N2 C17 C16 115.0(5) . . ? C18 C17 C16 124.0(6) . . ? C19 C18 C17 120.1(7) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 119.0(6) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C21 119.0(7) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? N2 C21 C20 121.8(7) . . ? N2 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.155 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.128