# 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 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wang Yaoyu' _publ_contact_author_email WYAOYU@NWU.EDU.CN _publ_section_title ; A series of Zn(II) coordination complexes derived from isomeric phenylenediacetic acid and dipyridyl ligands: syntheses, crystal structures, and characterizations ; loop_ _publ_author_name 'Wang Yaoyu.' 'Ai-Yun Fu.' E.Kh.Lermontova 'Rui-Ting Liu.' 'Qi-Zhen Shi.' ; G.-P.Yang ; 'Wei-Hong Zhang.' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 729341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 O6 Zn' _chemical_formula_sum 'C20 H20 N2 O6 Zn' _chemical_formula_weight 449.75 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.378(3) _cell_length_b 11.238(5) _cell_length_c 11.373(5) _cell_angle_alpha 90.253(6) _cell_angle_beta 94.771(6) _cell_angle_gamma 105.027(5) _cell_volume 907.2(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2545 _cell_measurement_theta_min 2.564 _cell_measurement_theta_max 27.516 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6713 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 4306 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3049 _reflns_number_gt 2702 _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^)+(0.1769P)^2^+24.4515P] 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 3049 _refine_ls_number_parameters 274 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.1002 _refine_ls_wR_factor_ref 0.3431 _refine_ls_wR_factor_gt 0.3411 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _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 0.75326(17) 0.25032(11) 0.32264(10) 0.0227(5) Uani 1 1 d . . . O1 O 0.7704(11) 0.0678(7) 0.3311(7) 0.0287(17) Uani 1 1 d . . . O2 O 1.0767(14) 0.0828(9) 0.3483(12) 0.059(3) Uani 1 1 d . . . O3 O 0.4378(14) -0.5792(9) 0.2989(12) 0.058(3) Uani 1 1 d . . . O4 O 0.7427(11) -0.5658(7) 0.3233(7) 0.0274(17) Uani 1 1 d . . . O5 O 0.4539(11) 0.1864(7) 0.2976(9) 0.036(2) Uani 1 1 d D . . O6 O 1.0526(11) 0.3129(7) 0.3459(9) 0.035(2) Uani 1 1 d D . . N1 N 0.7384(14) 0.2535(8) 0.5091(8) 0.028(2) Uani 1 1 d . . . N2 N 0.7572(14) 0.2491(9) 1.1344(8) 0.029(2) Uani 1 1 d . . . C1 C 0.9096(16) 0.0234(11) 0.3425(11) 0.031(3) Uani 1 1 d . . . C2 C 0.8658(17) -0.1185(10) 0.3509(10) 0.029(2) Uani 1 1 d . . . H2A H 0.9773 -0.1402 0.3853 0.034 Uiso 1 1 calc R . . H2B H 0.7669 -0.1462 0.4033 0.034 Uiso 1 1 calc R . . C3 C 0.8039(16) -0.1861(10) 0.2311(11) 0.028(2) Uani 1 1 d . . . C4 C 0.8529(19) -0.1255(12) 0.1267(12) 0.038(3) Uani 1 1 d . . . H4 H 0.9215 -0.0433 0.1305 0.046 Uiso 1 1 calc R . . C5 C 0.802(2) -0.1852(12) 0.0189(11) 0.039(3) Uani 1 1 d . . . H5A H 0.8365 -0.1433 -0.0494 0.047 Uiso 1 1 calc R . . C6 C 0.699(2) -0.3072(13) 0.0110(11) 0.042(3) Uani 1 1 d . . . H6A H 0.6606 -0.3472 -0.0621 0.050 Uiso 1 1 calc R . . C7 C 0.6529(18) -0.3688(11) 0.1143(12) 0.036(3) Uani 1 1 d . . . H7 H 0.5865 -0.4515 0.1094 0.043 Uiso 1 1 calc R . . C8 C 0.7036(15) -0.3107(10) 0.2251(10) 0.025(2) Uani 1 1 d . . . C9 C 0.6488(16) -0.3808(10) 0.3381(11) 0.029(2) Uani 1 1 d . . . H9A H 0.5394 -0.3596 0.3648 0.035 Uiso 1 1 calc R . . H9B H 0.7514 -0.3544 0.3993 0.035 Uiso 1 1 calc R . . C10 C 0.6041(16) -0.5215(11) 0.3207(11) 0.031(3) Uani 1 1 d . . . C11 C 0.6304(17) 0.1600(11) 0.5661(10) 0.029(2) Uani 1 1 d . . . H11 H 0.5509 0.0952 0.5207 0.035 Uiso 1 1 calc R . . C12 C 0.6295(16) 0.1536(10) 0.6870(10) 0.028(2) Uani 1 1 d . . . H12 H 0.5523 0.0860 0.7208 0.033 Uiso 1 1 calc R . . C13 C 0.7456(16) 0.2497(11) 0.7583(10) 0.029(2) Uani 1 1 d . . . C14 C 0.8548(16) 0.3483(10) 0.6988(10) 0.028(2) Uani 1 1 d . . . H14 H 0.9326 0.4157 0.7417 0.033 Uiso 1 1 calc R . . C15 C 0.8476(16) 0.3463(10) 0.5777(9) 0.027(2) Uani 1 1 d . . . H15 H 0.9226 0.4130 0.5413 0.032 Uiso 1 1 calc R . . C16 C 0.7488(16) 0.2486(11) 0.8883(10) 0.029(2) Uani 1 1 d . . . C17 C 0.7000(18) 0.1398(11) 0.9480(10) 0.033(3) Uani 1 1 d . . . H17 H 0.6633 0.0645 0.9069 0.040 Uiso 1 1 calc R . . C18 C 0.7065(18) 0.1446(12) 1.0705(10) 0.034(3) Uani 1 1 d . . . H18 H 0.6736 0.0707 1.1098 0.041 Uiso 1 1 calc R . . C19 C 0.8041(17) 0.3542(11) 1.0761(10) 0.031(3) Uani 1 1 d . . . H19 H 0.8397 0.4283 1.1194 0.037 Uiso 1 1 calc R . . C20 C 0.8020(18) 0.3578(11) 0.9546(10) 0.032(3) Uani 1 1 d . . . H20 H 0.8362 0.4329 0.9176 0.039 Uiso 1 1 calc R . . H5C H 0.357(8) 0.132(7) 0.304(12) 0.039 Uiso 1 1 d D . . H5D H 0.430(14) 0.249(6) 0.270(12) 0.039 Uiso 1 1 d D . . H6C H 1.152(8) 0.365(7) 0.341(12) 0.039 Uiso 1 1 d D . . H6D H 1.073(14) 0.248(6) 0.369(12) 0.039 Uiso 1 1 d 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 0.0280(8) 0.0186(7) 0.0216(7) 0.0016(5) 0.0034(5) 0.0061(5) O1 0.031(4) 0.020(4) 0.034(4) -0.001(3) 0.003(3) 0.004(3) O2 0.030(5) 0.033(5) 0.113(10) 0.001(6) 0.005(5) 0.009(4) O3 0.038(6) 0.022(5) 0.110(10) 0.001(5) 0.010(6) -0.001(4) O4 0.027(4) 0.020(4) 0.036(4) 0.001(3) 0.003(3) 0.007(3) O5 0.024(4) 0.015(4) 0.070(6) 0.011(4) 0.013(4) 0.007(3) O6 0.018(4) 0.014(4) 0.077(7) 0.011(4) 0.020(4) 0.005(3) N1 0.040(6) 0.022(5) 0.023(5) 0.002(4) 0.008(4) 0.005(4) N2 0.037(5) 0.028(5) 0.021(5) 0.002(4) 0.002(4) 0.006(4) C1 0.023(6) 0.034(6) 0.036(6) -0.004(5) 0.006(5) 0.007(5) C2 0.031(6) 0.022(6) 0.033(6) 0.000(5) -0.003(5) 0.008(5) C3 0.027(6) 0.018(5) 0.040(7) -0.002(5) 0.005(5) 0.006(4) C4 0.042(7) 0.027(6) 0.044(7) 0.002(5) 0.002(6) 0.004(5) C5 0.053(8) 0.034(7) 0.029(6) 0.008(5) 0.007(6) 0.008(6) C6 0.055(8) 0.042(7) 0.028(6) -0.008(5) -0.001(6) 0.013(6) C7 0.039(7) 0.023(6) 0.044(7) -0.002(5) -0.002(6) 0.006(5) C8 0.023(5) 0.016(5) 0.034(6) 0.000(4) -0.006(4) 0.005(4) C9 0.027(6) 0.024(6) 0.036(6) 0.002(5) 0.006(5) 0.005(5) C10 0.027(6) 0.026(6) 0.036(6) 0.003(5) 0.009(5) 0.000(5) C11 0.036(6) 0.025(6) 0.025(6) -0.002(4) 0.004(5) 0.005(5) C12 0.030(6) 0.027(6) 0.023(5) 0.001(4) 0.005(5) 0.002(5) C13 0.025(6) 0.029(6) 0.031(6) 0.001(5) 0.004(5) 0.004(5) C14 0.033(6) 0.021(6) 0.025(6) 0.000(4) 0.001(5) 0.003(5) C15 0.029(6) 0.023(6) 0.023(5) 0.002(4) 0.002(4) -0.002(4) C16 0.033(6) 0.030(6) 0.026(6) 0.003(5) 0.007(5) 0.012(5) C17 0.048(7) 0.021(6) 0.029(6) -0.005(5) 0.001(5) 0.006(5) C18 0.046(7) 0.034(7) 0.024(6) 0.005(5) 0.004(5) 0.012(6) C19 0.041(7) 0.029(6) 0.022(5) -0.001(5) 0.007(5) 0.008(5) C20 0.041(7) 0.029(6) 0.024(6) 0.002(5) 0.008(5) 0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.088(7) 1_565 ? Zn1 O1 2.090(8) . ? Zn1 O6 2.130(8) . ? Zn1 O5 2.132(8) . ? Zn1 N1 2.133(9) . ? Zn1 N2 2.143(9) 1_554 ? O1 C1 1.250(14) . ? O2 C1 1.237(15) . ? O3 C10 1.234(15) . ? O4 C10 1.247(14) . ? O4 Zn1 2.088(7) 1_545 ? O5 H5C 0.819(10) . ? O5 H5D 0.819(10) . ? O6 H6C 0.822(11) . ? O6 H6D 0.82(9) . ? N1 C15 1.342(14) . ? N1 C11 1.348(15) . ? N2 C18 1.330(16) . ? N2 C19 1.337(15) . ? N2 Zn1 2.143(9) 1_556 ? C1 C2 1.548(16) . ? C2 C3 1.532(16) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.398(18) . ? C3 C8 1.402(15) . ? C4 C5 1.371(18) . ? C4 H4 0.9300 . ? C5 C6 1.384(19) . ? C5 H5A 0.9300 . ? C6 C7 1.387(19) . ? C6 H6A 0.9300 . ? C7 C8 1.394(17) . ? C7 H7 0.9300 . ? C8 C9 1.538(16) . ? C9 C10 1.537(16) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.377(16) . ? C11 H11 0.9300 . ? C12 C13 1.398(16) . ? C12 H12 0.9300 . ? C13 C14 1.404(16) . ? C13 C16 1.476(16) . ? C14 C15 1.373(16) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.381(17) . ? C16 C20 1.386(17) . ? C17 C18 1.390(17) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.382(16) . ? C19 H19 0.9300 . ? C20 H20 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 O4 Zn1 O1 177.0(3) 1_565 . ? O4 Zn1 O6 88.5(3) 1_565 . ? O1 Zn1 O6 90.1(3) . . ? O4 Zn1 O5 91.8(3) 1_565 . ? O1 Zn1 O5 89.6(3) . . ? O6 Zn1 O5 179.3(4) . . ? O4 Zn1 N1 88.1(3) 1_565 . ? O1 Zn1 N1 89.3(3) . . ? O6 Zn1 N1 90.6(4) . . ? O5 Zn1 N1 89.9(4) . . ? O4 Zn1 N2 90.7(3) 1_565 1_554 ? O1 Zn1 N2 92.0(3) . 1_554 ? O6 Zn1 N2 91.4(4) . 1_554 ? O5 Zn1 N2 88.1(4) . 1_554 ? N1 Zn1 N2 177.6(4) . 1_554 ? C1 O1 Zn1 131.2(7) . . ? C10 O4 Zn1 129.8(7) . 1_545 ? Zn1 O5 H5C 150(7) . . ? Zn1 O5 H5D 99(7) . . ? H5C O5 H5D 111(2) . . ? Zn1 O6 H6C 152(7) . . ? Zn1 O6 H6D 98(7) . . ? H6C O6 H6D 110.4(19) . . ? C15 N1 C11 115.8(10) . . ? C15 N1 Zn1 121.2(7) . . ? C11 N1 Zn1 122.8(8) . . ? C18 N2 C19 117.3(10) . . ? C18 N2 Zn1 121.6(8) . 1_556 ? C19 N2 Zn1 121.1(8) . 1_556 ? O2 C1 O1 125.8(12) . . ? O2 C1 C2 118.0(11) . . ? O1 C1 C2 116.2(10) . . ? C3 C2 C1 113.2(9) . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C8 119.2(11) . . ? C4 C3 C2 120.3(10) . . ? C8 C3 C2 120.4(10) . . ? C5 C4 C3 121.1(12) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.5(12) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C7 118.7(12) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C6 C7 C8 122.0(12) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C7 C8 C3 118.4(11) . . ? C7 C8 C9 120.9(10) . . ? C3 C8 C9 120.7(10) . . ? C8 C9 C10 113.2(9) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? O3 C10 O4 125.9(11) . . ? O3 C10 C9 118.1(11) . . ? O4 C10 C9 115.9(10) . . ? N1 C11 C12 124.5(11) . . ? N1 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C11 C12 C13 119.5(11) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 115.9(10) . . ? C12 C13 C16 121.9(10) . . ? C14 C13 C16 122.2(11) . . ? C15 C14 C13 120.6(10) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N1 C15 C14 123.6(10) . . ? N1 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C17 C16 C20 117.7(11) . . ? C17 C16 C13 121.6(11) . . ? C20 C16 C13 120.8(11) . . ? C16 C17 C18 119.0(11) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? N2 C18 C17 123.5(11) . . ? N2 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? N2 C19 C20 123.0(11) . . ? N2 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? C19 C20 C16 119.6(11) . . ? C19 C20 H20 120.2 . . ? C16 C20 H20 120.2 . . ? 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 O4 Zn1 O1 C1 -64(6) 1_565 . . . ? O6 Zn1 O1 C1 -1.5(10) . . . . ? O5 Zn1 O1 C1 177.9(10) . . . . ? N1 Zn1 O1 C1 -92.2(10) . . . . ? N2 Zn1 O1 C1 89.9(10) 1_554 . . . ? O4 Zn1 N1 C15 -46.9(9) 1_565 . . . ? O1 Zn1 N1 C15 131.7(9) . . . . ? O6 Zn1 N1 C15 41.6(9) . . . . ? O5 Zn1 N1 C15 -138.7(9) . . . . ? N2 Zn1 N1 C15 -106(8) 1_554 . . . ? O4 Zn1 N1 C11 137.8(10) 1_565 . . . ? O1 Zn1 N1 C11 -43.6(9) . . . . ? O6 Zn1 N1 C11 -133.7(9) . . . . ? O5 Zn1 N1 C11 46.0(9) . . . . ? N2 Zn1 N1 C11 79(9) 1_554 . . . ? Zn1 O1 C1 O2 -2(2) . . . . ? Zn1 O1 C1 C2 177.3(7) . . . . ? O2 C1 C2 C3 -102.8(14) . . . . ? O1 C1 C2 C3 77.6(13) . . . . ? C1 C2 C3 C4 22.7(15) . . . . ? C1 C2 C3 C8 -159.7(10) . . . . ? C8 C3 C4 C5 1.2(19) . . . . ? C2 C3 C4 C5 178.8(12) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C4 C5 C6 C7 -2(2) . . . . ? C5 C6 C7 C8 2(2) . . . . ? C6 C7 C8 C3 -0.1(18) . . . . ? C6 C7 C8 C9 179.2(12) . . . . ? C4 C3 C8 C7 -1.3(17) . . . . ? C2 C3 C8 C7 -179.0(10) . . . . ? C4 C3 C8 C9 179.4(11) . . . . ? C2 C3 C8 C9 1.8(16) . . . . ? C7 C8 C9 C10 20.9(15) . . . . ? C3 C8 C9 C10 -159.8(10) . . . . ? Zn1 O4 C10 O3 -12(2) 1_545 . . . ? Zn1 O4 C10 C9 172.5(7) 1_545 . . . ? C8 C9 C10 O3 -95.4(14) . . . . ? C8 C9 C10 O4 80.5(13) . . . . ? C15 N1 C11 C12 -1.5(18) . . . . ? Zn1 N1 C11 C12 174.0(9) . . . . ? N1 C11 C12 C13 0.6(19) . . . . ? C11 C12 C13 C14 0.9(17) . . . . ? C11 C12 C13 C16 179.2(11) . . . . ? C12 C13 C14 C15 -1.4(17) . . . . ? C16 C13 C14 C15 -179.7(11) . . . . ? C11 N1 C15 C14 1.0(17) . . . . ? Zn1 N1 C15 C14 -174.7(9) . . . . ? C13 C14 C15 N1 0.5(19) . . . . ? C12 C13 C16 C17 25.5(18) . . . . ? C14 C13 C16 C17 -156.2(12) . . . . ? C12 C13 C16 C20 -154.8(12) . . . . ? C14 C13 C16 C20 23.5(18) . . . . ? C20 C16 C17 C18 0.0(18) . . . . ? C13 C16 C17 C18 179.7(11) . . . . ? C19 N2 C18 C17 -0.1(19) . . . . ? Zn1 N2 C18 C17 177.4(10) 1_556 . . . ? C16 C17 C18 N2 0(2) . . . . ? C18 N2 C19 C20 -0.2(18) . . . . ? Zn1 N2 C19 C20 -177.6(9) 1_556 . . . ? N2 C19 C20 C16 0.3(19) . . . . ? C17 C16 C20 C19 -0.2(18) . . . . ? C13 C16 C20 C19 -179.9(11) . . . . ? 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 O5 H5C O2 0.819(10) 2.10(7) 2.833(13) 148(11) 1_455 O5 H5D O3 0.819(10) 1.95(8) 2.667(12) 146(13) 1_565 O6 H6C O3 0.822(11) 2.13(6) 2.882(13) 152(11) 1_665 O6 H6D O2 0.82(9) 1.88(6) 2.638(12) 154(13) . _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 2.283 _refine_diff_density_min -1.310 _refine_diff_density_rms 0.217 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 729342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N2 O7 Zn' _chemical_formula_sum 'C22 H24 N2 O7 Zn' _chemical_formula_weight 493.80 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' 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' H H 0.0000 0.0000 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.2047(7) _cell_length_b 17.746(2) _cell_length_c 20.4535(19) _cell_angle_alpha 90.00 _cell_angle_beta 99.009(3) _cell_angle_gamma 90.00 _cell_volume 2224.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 771 _cell_measurement_theta_min 2.296 _cell_measurement_theta_max 16.576 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6756 _exptl_absorpt_correction_T_max 0.8649 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 11176 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0989 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3960 _reflns_number_gt 1966 _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^)+(0.0432P)^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 3960 _refine_ls_number_parameters 289 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.090 _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 0.06871(9) 0.48620(3) 0.28062(3) 0.0437(2) Uani 1 1 d . . . O1 O 0.0621(6) 0.3537(2) 0.3190(2) 0.0844(11) Uani 1 1 d U . . O2 O -0.1838(6) 0.4155(2) 0.25716(18) 0.0622(11) Uani 1 1 d . . . O3 O 0.1686(6) 0.1201(2) 0.30285(19) 0.0686(11) Uani 1 1 d . . . O4 O 0.0485(6) 0.08406(19) 0.20091(18) 0.0583(10) Uani 1 1 d . . . O5 O 0.9642(6) 0.1488(2) 0.4182(2) 0.0874(13) Uani 1 1 d . . . H5C H 0.8376 0.1635 0.4099 0.105 Uiso 1 1 d R . . H5D H 1.0226 0.1411 0.3856 0.105 Uiso 1 1 d R . . O6 O 0.5227(7) 0.2011(2) 0.3873(2) 0.1062(16) Uani 1 1 d . . . H6C H 0.4249 0.1783 0.3637 0.127 Uiso 1 1 d R . . H6D H 0.4312 0.2255 0.4032 0.127 Uiso 1 1 d R . . O7 O 0.2029(7) 0.2863(2) 0.4434(2) 0.0978(15) Uani 1 1 d . . . H7C H 0.1358 0.2466 0.4359 0.117 Uiso 1 1 d R . . H7D H 0.1618 0.3062 0.4074 0.117 Uiso 1 1 d R . . N1 N 0.1918(6) 0.4767(2) 0.19400(19) 0.0411(10) Uani 1 1 d . . . N2 N 0.3391(6) 0.4959(2) 0.35185(18) 0.0425(10) Uani 1 1 d . . . C1 C -0.1109(10) 0.3547(4) 0.2805(3) 0.0721(13) Uani 1 1 d U . . C2 C -0.2269(8) 0.2829(3) 0.2588(2) 0.0520(14) Uani 1 1 d . . . H2A H -0.3779 0.2860 0.2655 0.062 Uiso 1 1 calc R . . H2B H -0.1587 0.2412 0.2848 0.062 Uiso 1 1 calc R . . C3 C -0.2160(8) 0.2700(3) 0.1857(3) 0.0439(13) Uani 1 1 d . . . C4 C -0.3878(9) 0.2941(3) 0.1388(3) 0.0554(15) Uani 1 1 d . . . H4 H -0.5085 0.3164 0.1526 0.067 Uiso 1 1 calc R . . C5 C -0.3839(10) 0.2857(3) 0.0733(3) 0.0640(17) Uani 1 1 d . . . H5 H -0.5029 0.3008 0.0426 0.077 Uiso 1 1 calc R . . C6 C -0.2047(11) 0.2551(3) 0.0522(3) 0.0686(17) Uani 1 1 d . . . H6 H -0.1994 0.2506 0.0072 0.082 Uiso 1 1 calc R . . C7 C -0.0303(10) 0.2307(3) 0.0985(3) 0.0613(16) Uani 1 1 d . . . H7 H 0.0900 0.2091 0.0838 0.074 Uiso 1 1 calc R . . C8 C -0.0309(8) 0.2378(3) 0.1662(3) 0.0458(13) Uani 1 1 d . . . C9 C 0.1619(8) 0.2099(3) 0.2151(3) 0.0518(14) Uani 1 1 d . . . H9A H 0.2894 0.2073 0.1932 0.062 Uiso 1 1 calc R . . H9B H 0.1924 0.2458 0.2511 0.062 Uiso 1 1 calc R . . C10 C 0.1229(8) 0.1329(3) 0.2435(3) 0.0469(14) Uani 1 1 d . . . C11 C 0.3860(8) 0.5063(3) 0.1867(2) 0.0460(13) Uani 1 1 d . . . H11 H 0.4721 0.5268 0.2237 0.055 Uiso 1 1 calc R . . C12 C 0.4636(8) 0.5078(3) 0.1280(2) 0.0465(13) Uani 1 1 d . . . H12 H 0.5986 0.5297 0.1259 0.056 Uiso 1 1 calc R . . C13 C 0.3454(8) 0.4776(3) 0.0720(2) 0.0420(12) Uani 1 1 d . . . C14 C 0.1482(8) 0.4449(3) 0.0789(2) 0.0480(13) Uani 1 1 d . . . H14 H 0.0636 0.4225 0.0426 0.058 Uiso 1 1 calc R . . C15 C 0.0764(8) 0.4452(3) 0.1388(3) 0.0469(13) Uani 1 1 d . . . H15 H -0.0573 0.4230 0.1418 0.056 Uiso 1 1 calc R . . C16 C 0.4164(8) 0.4797(3) 0.0076(2) 0.0507(13) Uani 1 1 d . . . H16 H 0.3393 0.4504 -0.0258 0.061 Uiso 1 1 calc R . . C17 C 0.4814(8) 0.4393(3) 0.3659(3) 0.0554(15) Uani 1 1 d . . . H17 H 0.4514 0.3936 0.3441 0.066 Uiso 1 1 calc R . . C18 C 0.6689(8) 0.4454(3) 0.4108(3) 0.0560(15) Uani 1 1 d . . . H18 H 0.7626 0.4044 0.4188 0.067 Uiso 1 1 calc R . . C19 C 0.7201(8) 0.5130(3) 0.4446(2) 0.0477(13) Uani 1 1 d . . . C20 C 0.5722(8) 0.5708(3) 0.4306(3) 0.0521(14) Uani 1 1 d . . . H20 H 0.5973 0.6168 0.4523 0.062 Uiso 1 1 calc R . . C21 C 0.3883(8) 0.5607(3) 0.3849(3) 0.0525(14) Uani 1 1 d . . . H21 H 0.2920 0.6010 0.3762 0.063 Uiso 1 1 calc R . . C22 C 0.9198(8) 0.5243(3) 0.4922(2) 0.0532(15) Uani 1 1 d . . . H22 H 0.9349 0.5706 0.5137 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0445(4) 0.0452(4) 0.0400(4) -0.0015(3) 0.0026(3) -0.0009(3) O1 0.076(3) 0.082(2) 0.087(3) -0.015(2) -0.016(2) -0.014(2) O2 0.068(3) 0.055(3) 0.068(3) -0.004(2) 0.022(2) -0.011(2) O3 0.085(3) 0.064(3) 0.051(3) 0.005(2) -0.007(2) 0.009(2) O4 0.071(3) 0.048(2) 0.052(2) 0.0057(19) -0.004(2) -0.013(2) O5 0.082(3) 0.097(3) 0.083(3) -0.007(2) 0.010(2) 0.000(3) O6 0.081(3) 0.127(4) 0.106(4) -0.037(3) -0.001(3) 0.005(3) O7 0.112(4) 0.092(3) 0.085(4) -0.008(2) 0.002(3) -0.013(3) N1 0.036(2) 0.043(3) 0.043(3) 0.000(2) 0.004(2) 0.000(2) N2 0.041(2) 0.048(3) 0.038(2) -0.005(2) 0.0031(19) 0.000(2) C1 0.060(3) 0.075(3) 0.076(3) -0.014(3) -0.007(2) -0.013(3) C2 0.050(3) 0.055(4) 0.049(4) 0.002(3) 0.004(3) -0.009(3) C3 0.042(3) 0.038(3) 0.051(4) 0.000(3) 0.006(3) -0.014(3) C4 0.055(4) 0.052(4) 0.055(4) 0.005(3) -0.005(3) -0.007(3) C5 0.063(4) 0.061(4) 0.061(5) 0.011(3) -0.013(3) -0.003(3) C6 0.093(5) 0.070(4) 0.039(4) 0.006(3) -0.001(4) -0.013(4) C7 0.074(4) 0.049(4) 0.064(4) -0.002(3) 0.024(4) -0.003(3) C8 0.053(4) 0.036(3) 0.046(4) 0.004(3) 0.002(3) -0.012(3) C9 0.042(3) 0.051(4) 0.059(4) -0.001(3) -0.003(3) -0.007(3) C10 0.031(3) 0.047(4) 0.059(4) -0.003(3) -0.004(3) 0.004(3) C11 0.044(3) 0.052(3) 0.040(3) -0.007(3) 0.002(2) -0.007(3) C12 0.040(3) 0.058(4) 0.042(3) -0.003(3) 0.011(3) -0.011(3) C13 0.042(3) 0.046(3) 0.037(3) 0.000(2) 0.002(3) 0.004(3) C14 0.057(4) 0.053(3) 0.034(3) -0.004(3) 0.005(3) -0.012(3) C15 0.045(3) 0.051(3) 0.044(4) -0.001(3) 0.003(3) -0.011(3) C16 0.055(4) 0.055(4) 0.042(3) -0.001(3) 0.008(3) 0.001(3) C17 0.049(3) 0.062(4) 0.052(4) -0.016(3) -0.003(3) 0.006(3) C18 0.049(4) 0.057(4) 0.060(4) -0.010(3) 0.003(3) 0.013(3) C19 0.037(3) 0.065(4) 0.041(3) 0.000(3) 0.003(2) -0.003(3) C20 0.049(3) 0.052(4) 0.051(4) -0.006(3) -0.005(3) -0.007(3) C21 0.045(3) 0.052(4) 0.058(4) 0.001(3) 0.001(3) 0.003(3) C22 0.045(3) 0.063(4) 0.048(3) -0.001(3) -0.006(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.943(3) 2 ? Zn1 O2 2.006(4) . ? Zn1 N1 2.043(4) . ? Zn1 N2 2.050(4) . ? Zn1 O1 2.482(4) . ? O1 C1 1.228(6) . ? O2 C1 1.236(7) . ? O3 C10 1.224(6) . ? O4 C10 1.263(6) . ? O4 Zn1 1.943(3) 2_545 ? O5 H5C 0.8200 . ? O5 H5D 0.8201 . ? O6 H6C 0.8200 . ? O6 H6D 0.8201 . ? O7 H7C 0.8200 . ? O7 H7D 0.8201 . ? N1 C11 1.345(6) . ? N1 C15 1.359(6) . ? N2 C17 1.339(6) . ? N2 C21 1.345(6) . ? C1 C2 1.496(8) . ? C2 C3 1.523(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.386(7) . ? C3 C8 1.396(6) . ? C4 C5 1.352(7) . ? C4 H4 0.9300 . ? C5 C6 1.367(7) . ? C5 H5 0.9300 . ? C6 C7 1.391(7) . ? C6 H6 0.9300 . ? C7 C8 1.391(7) . ? C7 H7 0.9300 . ? C8 C9 1.518(6) . ? C9 C10 1.518(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.362(6) . ? C11 H11 0.9300 . ? C12 C13 1.369(6) . ? C12 H12 0.9300 . ? C13 C14 1.381(6) . ? C13 C16 1.453(6) . ? C14 C15 1.366(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C16 1.338(9) 3_665 ? C16 H16 0.9300 . ? C17 C18 1.369(6) . ? C17 H17 0.9300 . ? C18 C19 1.396(7) . ? C18 H18 0.9300 . ? C19 C20 1.377(6) . ? C19 C22 1.464(7) . ? C20 C21 1.369(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C22 1.317(9) 3_766 ? C22 H22 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 O4 Zn1 O2 107.69(15) 2 . ? O4 Zn1 N1 116.40(15) 2 . ? O2 Zn1 N1 97.17(15) . . ? O4 Zn1 N2 94.37(16) 2 . ? O2 Zn1 N2 138.10(16) . . ? N1 Zn1 N2 104.35(15) . . ? O4 Zn1 O1 139.52(15) 2 . ? O2 Zn1 O1 55.38(14) . . ? N1 Zn1 O1 102.87(14) . . ? N2 Zn1 O1 84.67(14) . . ? C1 O1 Zn1 80.7(4) . . ? C1 O2 Zn1 103.2(4) . . ? C10 O4 Zn1 125.9(4) . 2_545 ? H5C O5 H5D 114.5 . . ? H6C O6 H6D 89.9 . . ? H7C O7 H7D 97.2 . . ? C11 N1 C15 115.6(4) . . ? C11 N1 Zn1 121.9(3) . . ? C15 N1 Zn1 122.4(3) . . ? C17 N2 C21 116.4(4) . . ? C17 N2 Zn1 121.9(3) . . ? C21 N2 Zn1 121.7(3) . . ? O1 C1 O2 119.5(6) . . ? O1 C1 C2 120.6(6) . . ? O2 C1 C2 119.8(6) . . ? C1 C2 C3 109.1(4) . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C8 120.4(5) . . ? C4 C3 C2 119.0(5) . . ? C8 C3 C2 120.5(5) . . ? C5 C4 C3 121.5(6) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.8(6) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 119.6(6) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 121.8(5) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C3 116.9(5) . . ? C7 C8 C9 120.1(5) . . ? C3 C8 C9 122.9(5) . . ? C10 C9 C8 112.9(4) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? O3 C10 O4 124.0(5) . . ? O3 C10 C9 121.3(5) . . ? O4 C10 C9 114.7(5) . . ? N1 C11 C12 123.6(5) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C14 116.5(5) . . ? C12 C13 C16 123.3(5) . . ? C14 C13 C16 120.2(5) . . ? C15 C14 C13 120.6(5) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N1 C15 C14 122.9(4) . . ? N1 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C16 C16 C13 125.5(6) 3_665 . ? C16 C16 H16 117.2 3_665 . ? C13 C16 H16 117.2 . . ? N2 C17 C18 123.1(5) . . ? N2 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C19 120.3(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 116.4(5) . . ? C20 C19 C22 120.2(5) . . ? C18 C19 C22 123.4(5) . . ? C21 C20 C19 120.1(5) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? N2 C21 C20 123.7(5) . . ? N2 C21 H21 118.2 . . ? C20 C21 H21 118.2 . . ? C22 C22 C19 126.9(7) 3_766 . ? C22 C22 H22 116.6 3_766 . ? C19 C22 H22 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O1 C1 82.5(4) 2 . . . ? O2 Zn1 O1 C1 6.4(4) . . . . ? N1 Zn1 O1 C1 -83.4(4) . . . . ? N2 Zn1 O1 C1 173.0(4) . . . . ? O4 Zn1 O2 C1 -145.1(4) 2 . . . ? N1 Zn1 O2 C1 94.2(4) . . . . ? N2 Zn1 O2 C1 -26.7(5) . . . . ? O1 Zn1 O2 C1 -6.5(4) . . . . ? O4 Zn1 N1 C11 75.3(4) 2 . . . ? O2 Zn1 N1 C11 -170.8(4) . . . . ? N2 Zn1 N1 C11 -27.1(4) . . . . ? O1 Zn1 N1 C11 -114.8(3) . . . . ? O4 Zn1 N1 C15 -99.6(4) 2 . . . ? O2 Zn1 N1 C15 14.2(4) . . . . ? N2 Zn1 N1 C15 158.0(3) . . . . ? O1 Zn1 N1 C15 70.3(4) . . . . ? O4 Zn1 N2 C17 175.0(4) 2 . . . ? O2 Zn1 N2 C17 52.2(4) . . . . ? N1 Zn1 N2 C17 -66.3(4) . . . . ? O1 Zn1 N2 C17 35.6(4) . . . . ? O4 Zn1 N2 C21 -8.0(4) 2 . . . ? O2 Zn1 N2 C21 -130.8(4) . . . . ? N1 Zn1 N2 C21 110.6(4) . . . . ? O1 Zn1 N2 C21 -147.4(4) . . . . ? Zn1 O1 C1 O2 -9.9(6) . . . . ? Zn1 O1 C1 C2 166.4(6) . . . . ? Zn1 O2 C1 O1 12.5(7) . . . . ? Zn1 O2 C1 C2 -163.9(4) . . . . ? O1 C1 C2 C3 -110.9(6) . . . . ? O2 C1 C2 C3 65.4(7) . . . . ? C1 C2 C3 C4 -94.6(6) . . . . ? C1 C2 C3 C8 82.1(6) . . . . ? C8 C3 C4 C5 1.5(7) . . . . ? C2 C3 C4 C5 178.2(5) . . . . ? C3 C4 C5 C6 -2.0(8) . . . . ? C4 C5 C6 C7 1.9(8) . . . . ? C5 C6 C7 C8 -1.2(8) . . . . ? C6 C7 C8 C3 0.6(7) . . . . ? C6 C7 C8 C9 179.5(5) . . . . ? C4 C3 C8 C7 -0.8(7) . . . . ? C2 C3 C8 C7 -177.4(4) . . . . ? C4 C3 C8 C9 -179.5(4) . . . . ? C2 C3 C8 C9 3.8(7) . . . . ? C7 C8 C9 C10 -99.3(6) . . . . ? C3 C8 C9 C10 79.5(6) . . . . ? Zn1 O4 C10 O3 14.0(7) 2_545 . . . ? Zn1 O4 C10 C9 -168.4(3) 2_545 . . . ? C8 C9 C10 O3 -134.2(5) . . . . ? C8 C9 C10 O4 48.2(6) . . . . ? C15 N1 C11 C12 2.1(7) . . . . ? Zn1 N1 C11 C12 -173.1(4) . . . . ? N1 C11 C12 C13 -0.9(8) . . . . ? C11 C12 C13 C14 -1.1(7) . . . . ? C11 C12 C13 C16 177.9(5) . . . . ? C12 C13 C14 C15 1.6(7) . . . . ? C16 C13 C14 C15 -177.5(5) . . . . ? C11 N1 C15 C14 -1.6(7) . . . . ? Zn1 N1 C15 C14 173.7(4) . . . . ? C13 C14 C15 N1 -0.3(8) . . . . ? C12 C13 C16 C16 -10.8(10) . . . 3_665 ? C14 C13 C16 C16 168.1(6) . . . 3_665 ? C21 N2 C17 C18 -0.5(7) . . . . ? Zn1 N2 C17 C18 176.6(4) . . . . ? N2 C17 C18 C19 0.0(8) . . . . ? C17 C18 C19 C20 0.7(7) . . . . ? C17 C18 C19 C22 -178.6(5) . . . . ? C18 C19 C20 C21 -1.0(7) . . . . ? C22 C19 C20 C21 178.4(5) . . . . ? C17 N2 C21 C20 0.2(7) . . . . ? Zn1 N2 C21 C20 -176.9(4) . . . . ? C19 C20 C21 N2 0.5(8) . . . . ? C20 C19 C22 C22 -176.2(6) . . . 3_766 ? C18 C19 C22 C22 3.1(10) . . . 3_766 ? 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 O7 H7D O1 0.82 2.00 2.823(6) 179.4 . O7 H7C O5 0.82 2.04 2.859(5) 178.9 1_455 O6 H6D O7 0.82 2.05 2.872(6) 179.6 . O6 H6C O3 0.82 2.13 2.948(6) 179.4 . O5 H5D O3 0.82 2.07 2.894(5) 179.3 1_655 O5 H5C O6 0.82 2.05 2.867(6) 178.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.711 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.073 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 729343' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 O6 Zn' _chemical_formula_sum 'C20 H20 N2 O6 Zn' _chemical_formula_weight 449.75 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3194(11) _cell_length_b 11.3886(15) _cell_length_c 11.444(3) _cell_angle_alpha 109.818(3) _cell_angle_beta 92.908(3) _cell_angle_gamma 111.323(2) _cell_volume 931.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1166 _cell_measurement_theta_min 2.228 _cell_measurement_theta_max 21.889 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 1.361 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6777 _exptl_absorpt_correction_T_max 0.8323 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 4703 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3256 _reflns_number_gt 2408 _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^)+(0.0850P)^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 3256 _refine_ls_number_parameters 268 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.093 _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 0.41517(6) 0.32139(5) 0.24840(5) 0.0327(2) Uani 1 1 d . . . O1 O 0.2239(4) 0.3668(3) 0.1587(3) 0.0386(7) Uani 1 1 d . . . O2 O 0.2891(4) 0.4591(3) 0.3664(3) 0.0411(8) Uani 1 1 d . . . O3 O 0.5029(4) 0.7817(3) -0.0986(3) 0.0430(8) Uani 1 1 d . . . O4 O 0.2606(5) 0.7511(5) -0.2191(3) 0.0678(11) Uani 1 1 d . . . O5 O 0.5817(4) 0.3364(3) 0.4020(3) 0.0371(7) Uani 1 1 d D . . O6 O 0.0778(14) 0.7523(10) 0.5830(9) 0.257(5) Uani 1 1 d DU . . H6C H 0.0849 0.7679 0.6591 0.308 Uiso 1 1 d RD . . H6D H -0.0158 0.6948 0.5411 0.308 Uiso 1 1 d RD . . N1 N 0.6134(5) 0.5125(4) 0.2508(3) 0.0338(8) Uani 1 1 d . . . N2 N 1.2182(5) 1.1402(3) 0.2543(3) 0.0313(8) Uani 1 1 d . . . C1 C 0.2155(5) 0.4487(4) 0.2619(4) 0.0322(10) Uani 1 1 d . . . C2 C 0.1255(6) 0.5449(5) 0.2617(5) 0.0411(11) Uani 1 1 d . . . H2A H 0.0209 0.4966 0.1952 0.049 Uiso 1 1 calc R . . H2B H 0.0900 0.5751 0.3422 0.049 Uiso 1 1 calc R . . C3 C 0.2508(6) 0.6674(5) 0.2403(4) 0.0382(11) Uani 1 1 d . . . C4 C 0.3993(7) 0.7623(5) 0.3317(5) 0.0462(12) Uani 1 1 d . . . H4 H 0.4229 0.7499 0.4060 0.055 Uiso 1 1 calc R . . C5 C 0.5133(6) 0.8760(5) 0.3132(5) 0.0497(13) Uani 1 1 d . . . H5A H 0.6145 0.9378 0.3739 0.060 Uiso 1 1 calc R . . C6 C 0.4770(6) 0.8974(5) 0.2058(5) 0.0463(12) Uani 1 1 d . . . H6 H 0.5536 0.9741 0.1946 0.056 Uiso 1 1 calc R . . C7 C 0.3269(6) 0.8056(5) 0.1133(4) 0.0371(11) Uani 1 1 d . . . C8 C 0.2182(6) 0.6909(4) 0.1321(4) 0.0351(10) Uani 1 1 d . . . H8 H 0.1196 0.6273 0.0697 0.042 Uiso 1 1 calc R . . C9 C 0.2774(7) 0.8338(5) 0.0007(5) 0.0450(12) Uani 1 1 d . . . H9A H 0.3146 0.9317 0.0269 0.054 Uiso 1 1 calc R . . H9B H 0.1500 0.7925 -0.0242 0.054 Uiso 1 1 calc R . . C10 C 0.3529(7) 0.7836(5) -0.1152(5) 0.0399(11) Uani 1 1 d . . . C11 C 0.6375(6) 0.5300(5) 0.1427(4) 0.0378(11) Uani 1 1 d . . . H11 H 0.5758 0.4565 0.0670 0.045 Uiso 1 1 calc R . . C12 C 0.7492(6) 0.6513(4) 0.1369(4) 0.0389(11) Uani 1 1 d . . . H12 H 0.7581 0.6595 0.0591 0.047 Uiso 1 1 calc R . . C13 C 0.8480(5) 0.7608(4) 0.2484(4) 0.0306(10) Uani 1 1 d . . . C14 C 0.8267(6) 0.7410(5) 0.3612(4) 0.0389(11) Uani 1 1 d . . . H14 H 0.8924 0.8106 0.4381 0.047 Uiso 1 1 calc R . . C15 C 0.7080(6) 0.6180(4) 0.3585(4) 0.0370(11) Uani 1 1 d . . . H15 H 0.6930 0.6078 0.4350 0.044 Uiso 1 1 calc R . . C16 C 0.9720(6) 0.8915(4) 0.2496(4) 0.0310(10) Uani 1 1 d . . . C17 C 0.9380(6) 0.9501(5) 0.1686(4) 0.0394(11) Uani 1 1 d . . . H17 H 0.8318 0.9069 0.1107 0.047 Uiso 1 1 calc R . . C18 C 1.0620(6) 1.0727(5) 0.1738(4) 0.0420(12) Uani 1 1 d . . . H18 H 1.0358 1.1104 0.1188 0.050 Uiso 1 1 calc R . . C19 C 1.2501(6) 1.0841(4) 0.3324(4) 0.0357(10) Uani 1 1 d . . . H19 H 1.3581 1.1288 0.3884 0.043 Uiso 1 1 calc R . . C20 C 1.1330(6) 0.9641(4) 0.3351(4) 0.0347(10) Uani 1 1 d . . . H20 H 1.1608 0.9312 0.3939 0.042 Uiso 1 1 calc R . . H5C H 0.628(4) 0.397(3) 0.473(2) 0.042 Uiso 1 1 d D . . H5D H 0.658(4) 0.318(4) 0.366(3) 0.042 Uiso 1 1 d 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 0.0365(3) 0.0233(3) 0.0331(3) 0.0136(2) 0.0071(2) 0.0040(2) O1 0.0432(18) 0.0322(18) 0.0336(18) 0.0118(15) 0.0078(14) 0.0089(14) O2 0.054(2) 0.0349(18) 0.0305(18) 0.0134(15) 0.0043(15) 0.0132(15) O3 0.0400(19) 0.0348(18) 0.044(2) 0.0100(15) 0.0154(15) 0.0087(15) O4 0.080(3) 0.099(3) 0.047(2) 0.034(2) 0.020(2) 0.055(3) O5 0.0394(17) 0.0335(19) 0.0323(18) 0.0144(14) 0.0045(14) 0.0069(14) O6 0.255(5) 0.260(5) 0.254(5) 0.098(3) 0.049(2) 0.105(3) N1 0.039(2) 0.027(2) 0.030(2) 0.0139(17) 0.0060(16) 0.0054(16) N2 0.037(2) 0.0216(19) 0.032(2) 0.0116(16) 0.0043(16) 0.0069(16) C1 0.033(2) 0.025(2) 0.036(3) 0.015(2) 0.006(2) 0.0055(19) C2 0.037(3) 0.035(3) 0.056(3) 0.022(2) 0.016(2) 0.015(2) C3 0.042(3) 0.035(3) 0.046(3) 0.021(2) 0.013(2) 0.019(2) C4 0.057(3) 0.041(3) 0.040(3) 0.019(2) 0.001(2) 0.018(3) C5 0.040(3) 0.041(3) 0.059(3) 0.021(3) -0.001(2) 0.007(2) C6 0.040(3) 0.036(3) 0.069(4) 0.027(3) 0.019(3) 0.014(2) C7 0.049(3) 0.038(3) 0.040(3) 0.021(2) 0.019(2) 0.027(2) C8 0.035(2) 0.030(2) 0.038(3) 0.010(2) 0.007(2) 0.014(2) C9 0.064(3) 0.042(3) 0.047(3) 0.025(2) 0.022(2) 0.032(3) C10 0.051(3) 0.028(3) 0.046(3) 0.021(2) 0.020(2) 0.014(2) C11 0.034(2) 0.031(3) 0.038(3) 0.015(2) 0.002(2) 0.002(2) C12 0.049(3) 0.029(2) 0.027(2) 0.013(2) 0.003(2) 0.002(2) C13 0.029(2) 0.027(2) 0.034(2) 0.015(2) 0.0087(19) 0.0067(19) C14 0.042(3) 0.029(2) 0.034(3) 0.010(2) 0.007(2) 0.004(2) C15 0.048(3) 0.026(2) 0.029(2) 0.013(2) 0.008(2) 0.004(2) C16 0.037(2) 0.024(2) 0.029(2) 0.0091(19) 0.0105(19) 0.0088(19) C17 0.035(2) 0.030(3) 0.046(3) 0.021(2) 0.000(2) 0.001(2) C18 0.043(3) 0.038(3) 0.040(3) 0.022(2) 0.002(2) 0.006(2) C19 0.036(2) 0.026(2) 0.035(3) 0.011(2) 0.000(2) 0.0051(19) C20 0.039(3) 0.028(2) 0.037(3) 0.018(2) 0.006(2) 0.008(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 Zn1 O3 2.029(3) 2_665 ? Zn1 O5 2.102(3) . ? Zn1 N2 2.143(3) 1_445 ? Zn1 O1 2.156(3) . ? Zn1 N1 2.192(3) . ? Zn1 O2 2.299(3) . ? O1 C1 1.256(5) . ? O2 C1 1.264(5) . ? O3 C10 1.261(6) . ? O3 Zn1 2.029(3) 2_665 ? O4 C10 1.242(6) . ? O5 H5C 0.822(10) . ? O5 H5D 0.825(10) . ? O6 H6C 0.8226 . ? O6 H6D 0.8018 . ? N1 C11 1.332(5) . ? N1 C15 1.339(5) . ? N2 C19 1.328(5) . ? N2 C18 1.342(6) . ? N2 Zn1 2.143(3) 1_665 ? C1 C2 1.536(6) . ? C2 C3 1.514(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.385(7) . ? C3 C8 1.387(6) . ? C4 C5 1.391(7) . ? C4 H4 0.9300 . ? C5 C6 1.370(7) . ? C5 H5A 0.9300 . ? C6 C7 1.392(7) . ? C6 H6 0.9300 . ? C7 C8 1.386(6) . ? C7 C9 1.502(6) . ? C8 H8 0.9300 . ? C9 C10 1.521(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.383(6) . ? C11 H11 0.9300 . ? C12 C13 1.389(6) . ? C12 H12 0.9300 . ? C13 C14 1.393(6) . ? C13 C16 1.465(6) . ? C14 C15 1.379(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.384(6) . ? C16 C20 1.396(6) . ? C17 C18 1.382(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.372(6) . ? C19 H19 0.9300 . ? C20 H20 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 O3 Zn1 O5 101.67(13) 2_665 . ? O3 Zn1 N2 94.16(13) 2_665 1_445 ? O5 Zn1 N2 89.96(12) . 1_445 ? O3 Zn1 O1 102.56(13) 2_665 . ? O5 Zn1 O1 155.35(13) . . ? N2 Zn1 O1 92.79(12) 1_445 . ? O3 Zn1 N1 88.65(13) 2_665 . ? O5 Zn1 N1 89.27(13) . . ? N2 Zn1 N1 177.18(13) 1_445 . ? O1 Zn1 N1 86.79(12) . . ? O3 Zn1 O2 160.46(12) 2_665 . ? O5 Zn1 O2 96.52(12) . . ? N2 Zn1 O2 92.95(12) 1_445 . ? O1 Zn1 O2 58.89(11) . . ? N1 Zn1 O2 84.45(13) . . ? C1 O1 Zn1 93.0(2) . . ? C1 O2 Zn1 86.3(3) . . ? C10 O3 Zn1 119.3(3) . 2_665 ? Zn1 O5 H5C 132(3) . . ? Zn1 O5 H5D 100(3) . . ? H5C O5 H5D 109.5(18) . . ? H6C O6 H6D 113.0 . . ? C11 N1 C15 117.2(4) . . ? C11 N1 Zn1 120.1(3) . . ? C15 N1 Zn1 122.5(3) . . ? C19 N2 C18 116.7(4) . . ? C19 N2 Zn1 121.2(3) . 1_665 ? C18 N2 Zn1 122.0(3) . 1_665 ? O1 C1 O2 121.0(4) . . ? O1 C1 C2 119.8(4) . . ? O2 C1 C2 119.0(4) . . ? C3 C2 C1 110.0(4) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C8 118.1(4) . . ? C4 C3 C2 120.3(4) . . ? C8 C3 C2 121.6(4) . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.2(5) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 117.9(4) . . ? C8 C7 C9 120.7(4) . . ? C6 C7 C9 121.3(4) . . ? C7 C8 C3 122.5(4) . . ? C7 C8 H8 118.8 . . ? C3 C8 H8 118.8 . . ? C7 C9 C10 116.4(4) . . ? C7 C9 H9A 108.2 . . ? C10 C9 H9A 108.2 . . ? C7 C9 H9B 108.2 . . ? C10 C9 H9B 108.2 . . ? H9A C9 H9B 107.3 . . ? O4 C10 O3 125.8(5) . . ? O4 C10 C9 115.7(5) . . ? O3 C10 C9 118.5(4) . . ? N1 C11 C12 123.6(4) . . ? N1 C11 H11 118.2 . . ? C12 C11 H11 118.2 . . ? C11 C12 C13 119.4(4) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 117.0(4) . . ? C12 C13 C16 122.5(4) . . ? C14 C13 C16 120.5(4) . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? N1 C15 C14 123.0(4) . . ? N1 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C17 C16 C20 116.4(4) . . ? C17 C16 C13 123.0(4) . . ? C20 C16 C13 120.6(4) . . ? C18 C17 C16 120.0(4) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? N2 C18 C17 123.2(4) . . ? N2 C18 H18 118.4 . . ? C17 C18 H18 118.4 . . ? N2 C19 C20 123.8(4) . . ? N2 C19 H19 118.1 . . ? C20 C19 H19 118.1 . . ? C19 C20 C16 120.0(4) . . ? C19 C20 H20 120.0 . . ? C16 C20 H20 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C1 -168.3(2) 2_665 . . . ? O5 Zn1 O1 C1 0.8(4) . . . . ? N2 Zn1 O1 C1 96.8(2) 1_445 . . . ? N1 Zn1 O1 C1 -80.4(2) . . . . ? O2 Zn1 O1 C1 5.0(2) . . . . ? O3 Zn1 O2 C1 14.8(5) 2_665 . . . ? O5 Zn1 O2 C1 173.2(2) . . . . ? N2 Zn1 O2 C1 -96.5(2) 1_445 . . . ? O1 Zn1 O2 C1 -5.0(2) . . . . ? N1 Zn1 O2 C1 84.6(2) . . . . ? O3 Zn1 N1 C11 42.9(3) 2_665 . . . ? O5 Zn1 N1 C11 144.6(4) . . . . ? N2 Zn1 N1 C11 -141(3) 1_445 . . . ? O1 Zn1 N1 C11 -59.8(3) . . . . ? O2 Zn1 N1 C11 -118.8(3) . . . . ? O3 Zn1 N1 C15 -140.6(4) 2_665 . . . ? O5 Zn1 N1 C15 -38.9(4) . . . . ? N2 Zn1 N1 C15 35(3) 1_445 . . . ? O1 Zn1 N1 C15 116.8(4) . . . . ? O2 Zn1 N1 C15 57.7(4) . . . . ? Zn1 O1 C1 O2 -9.2(4) . . . . ? Zn1 O1 C1 C2 166.7(3) . . . . ? Zn1 O2 C1 O1 8.6(4) . . . . ? Zn1 O2 C1 C2 -167.3(3) . . . . ? O1 C1 C2 C3 -80.8(5) . . . . ? O2 C1 C2 C3 95.1(5) . . . . ? C1 C2 C3 C4 -67.7(6) . . . . ? C1 C2 C3 C8 114.7(5) . . . . ? C8 C3 C4 C5 -1.3(7) . . . . ? C2 C3 C4 C5 -179.0(4) . . . . ? C3 C4 C5 C6 1.9(8) . . . . ? C4 C5 C6 C7 -0.5(8) . . . . ? C5 C6 C7 C8 -1.5(7) . . . . ? C5 C6 C7 C9 174.7(5) . . . . ? C6 C7 C8 C3 2.1(7) . . . . ? C9 C7 C8 C3 -174.1(4) . . . . ? C4 C3 C8 C7 -0.7(7) . . . . ? C2 C3 C8 C7 177.0(4) . . . . ? C8 C7 C9 C10 -94.6(5) . . . . ? C6 C7 C9 C10 89.4(6) . . . . ? Zn1 O3 C10 O4 -15.2(6) 2_665 . . . ? Zn1 O3 C10 C9 166.9(3) 2_665 . . . ? C7 C9 C10 O4 149.5(5) . . . . ? C7 C9 C10 O3 -32.4(6) . . . . ? C15 N1 C11 C12 -2.3(7) . . . . ? Zn1 N1 C11 C12 174.5(4) . . . . ? N1 C11 C12 C13 2.5(7) . . . . ? C11 C12 C13 C14 -0.4(7) . . . . ? C11 C12 C13 C16 178.6(4) . . . . ? C12 C13 C14 C15 -1.7(7) . . . . ? C16 C13 C14 C15 179.3(4) . . . . ? C11 N1 C15 C14 0.0(7) . . . . ? Zn1 N1 C15 C14 -176.7(3) . . . . ? C13 C14 C15 N1 2.0(7) . . . . ? C12 C13 C16 C17 39.1(7) . . . . ? C14 C13 C16 C17 -142.0(5) . . . . ? C12 C13 C16 C20 -141.2(5) . . . . ? C14 C13 C16 C20 37.7(6) . . . . ? C20 C16 C17 C18 1.2(7) . . . . ? C13 C16 C17 C18 -179.1(4) . . . . ? C19 N2 C18 C17 -0.7(7) . . . . ? Zn1 N2 C18 C17 174.7(4) 1_665 . . . ? C16 C17 C18 N2 0.4(8) . . . . ? C18 N2 C19 C20 -0.6(7) . . . . ? Zn1 N2 C19 C20 -176.1(3) 1_665 . . . ? N2 C19 C20 C16 2.2(7) . . . . ? C17 C16 C20 C19 -2.4(7) . . . . ? C13 C16 C20 C19 177.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.573 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.099 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 729344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N2 O6 Zn' _chemical_formula_sum 'C22 H24 N2 O6 Zn' _chemical_formula_weight 477.80 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8963(8) _cell_length_b 9.4798(12) _cell_length_c 16.697(2) _cell_angle_alpha 90.660(2) _cell_angle_beta 101.526(2) _cell_angle_gamma 91.251(2) _cell_volume 1069.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1362 _cell_measurement_theta_min 2.490 _cell_measurement_theta_max 22.308 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8417 _exptl_absorpt_correction_T_max 0.9108 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 5374 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3727 _reflns_number_gt 2748 _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^)+(0.1271P)^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 3727 _refine_ls_number_parameters 280 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1919 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 0.87533(8) 0.76502(6) 0.19431(3) 0.0377(3) Uani 1 1 d . . . O1 O 1.1544(8) 0.8636(5) 0.3356(3) 0.0840(15) Uani 1 1 d . . . O2 O 0.9673(6) 0.9590(4) 0.2298(2) 0.0525(10) Uani 1 1 d . . . O3 O 0.8403(6) 1.5095(5) 0.1111(3) 0.0646(12) Uani 1 1 d . . . O4 O 1.0853(5) 1.6605(4) 0.1615(2) 0.0530(10) Uani 1 1 d . . . N1 N 0.6260(6) 0.8253(4) 0.1121(2) 0.0355(9) Uani 1 1 d . . . N2 N 0.7523(6) 0.6624(5) 0.2798(3) 0.0432(10) Uani 1 1 d . . . O5 O 0.442(3) 0.0839(19) 0.5506(12) 0.382(10) Uani 1 1 d U . . H5C H 0.4793 0.0279 0.5193 0.458 Uiso 1 1 d R . . H5D H 0.5508 0.0984 0.5804 0.458 Uiso 1 1 d R . . O6 O 0.019(2) 0.1679(17) 0.5181(11) 0.341(8) Uani 1 1 d U . . H6D H 0.1362 0.1465 0.5270 0.409 Uiso 1 1 d R . . H6C H -0.0242 0.1616 0.5602 0.409 Uiso 1 1 d R . . C1 C 1.0844(8) 0.9684(6) 0.2974(3) 0.0462(13) Uani 1 1 d . . . C2 C 1.1403(9) 1.1147(6) 0.3312(3) 0.0506(14) Uani 1 1 d . . . H2A H 1.2171 1.1082 0.3863 0.061 Uiso 1 1 calc R . . H2B H 1.0208 1.1650 0.3340 0.061 Uiso 1 1 calc R . . C3 C 1.2603(8) 1.1983(5) 0.2793(3) 0.0429(12) Uani 1 1 d . . . C4 C 1.4643(9) 1.1897(6) 0.2914(4) 0.0569(16) Uani 1 1 d . . . H4 H 1.5300 1.1321 0.3322 0.068 Uiso 1 1 calc R . . C5 C 1.5702(8) 1.2630(7) 0.2452(4) 0.0617(17) Uani 1 1 d . . . H5 H 1.7072 1.2558 0.2551 0.074 Uiso 1 1 calc R . . C6 C 1.4779(9) 1.3478(6) 0.1839(4) 0.0563(16) Uani 1 1 d . . . H6 H 1.5519 1.3980 0.1525 0.068 Uiso 1 1 calc R . . C7 C 1.2709(8) 1.3585(5) 0.1688(3) 0.0427(13) Uani 1 1 d . . . C8 C 1.1665(7) 1.2837(5) 0.2168(3) 0.0390(12) Uani 1 1 d . . . H8 H 1.0295 1.2903 0.2072 0.047 Uiso 1 1 calc R . . C9 C 1.1704(9) 1.4501(6) 0.1004(4) 0.0513(14) Uani 1 1 d . . . H9A H 1.2699 1.5075 0.0816 0.062 Uiso 1 1 calc R . . H9B H 1.1052 1.3902 0.0551 0.062 Uiso 1 1 calc R . . C10 C 1.0197(8) 1.5454(6) 0.1256(3) 0.0443(13) Uani 1 1 d . . . C11 C 0.5419(7) 0.9431(6) 0.1311(3) 0.0465(13) Uani 1 1 d . . . H11 H 0.6122 1.0012 0.1727 0.056 Uiso 1 1 calc R . . C12 C 0.3584(8) 0.9828(5) 0.0928(3) 0.0437(13) Uani 1 1 d . . . H12 H 0.3059 1.0655 0.1090 0.052 Uiso 1 1 calc R . . C13 C 0.2505(7) 0.9011(5) 0.0303(3) 0.0359(11) Uani 1 1 d . . . C14 C 0.3408(7) 0.7810(6) 0.0085(3) 0.0422(12) Uani 1 1 d . . . H14 H 0.2761 0.7237 -0.0347 0.051 Uiso 1 1 calc R . . C15 C 0.5262(7) 0.7466(5) 0.0505(3) 0.0399(12) Uani 1 1 d . . . H15 H 0.5836 0.6653 0.0353 0.048 Uiso 1 1 calc R . . C16 C 0.0432(8) 0.9336(6) -0.0136(3) 0.0452(13) Uani 1 1 d . . . H16A H 0.0431 0.9402 -0.0715 0.054 Uiso 1 1 calc R . . H16B H -0.0434 0.8546 -0.0067 0.054 Uiso 1 1 calc R . . C17 C 0.5638(9) 0.6780(7) 0.2852(4) 0.0610(16) Uani 1 1 d . . . H17 H 0.4853 0.7366 0.2486 0.073 Uiso 1 1 calc R . . C18 C 0.4808(10) 0.6097(8) 0.3437(4) 0.072(2) Uani 1 1 d . . . H18 H 0.3484 0.6232 0.3452 0.086 Uiso 1 1 calc R . . C19 C 0.5904(10) 0.5223(7) 0.3995(4) 0.0588(16) Uani 1 1 d . . . C20 C 0.7858(10) 0.5069(7) 0.3923(4) 0.0633(17) Uani 1 1 d . . . H20 H 0.8678 0.4491 0.4282 0.076 Uiso 1 1 calc R . . C21 C 0.8591(9) 0.5763(7) 0.3324(4) 0.0559(15) Uani 1 1 d . . . H21 H 0.9900 0.5623 0.3286 0.067 Uiso 1 1 calc R . . C22 C 0.5023(14) 0.4533(8) 0.4641(5) 0.085(2) Uani 1 1 d . . . H22A H 0.5777 0.3706 0.4826 0.102 Uiso 1 1 calc R . . H22B H 0.3682 0.4218 0.4403 0.102 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0336(4) 0.0372(4) 0.0431(4) 0.0057(3) 0.0092(3) 0.0037(2) O1 0.112(4) 0.050(3) 0.079(3) 0.004(2) -0.009(3) 0.008(3) O2 0.051(2) 0.044(2) 0.058(3) 0.0002(18) 0.0003(19) -0.0024(18) O3 0.048(3) 0.061(3) 0.084(3) -0.007(2) 0.012(2) 0.001(2) O4 0.046(2) 0.043(2) 0.074(3) -0.007(2) 0.022(2) -0.0006(17) N1 0.032(2) 0.033(2) 0.041(2) 0.0019(18) 0.0055(18) 0.0046(17) N2 0.037(2) 0.053(3) 0.039(2) 0.008(2) 0.0062(19) -0.002(2) O5 0.384(10) 0.380(10) 0.380(10) 0.006(2) 0.073(3) 0.012(2) O6 0.342(9) 0.341(9) 0.339(9) 0.004(2) 0.069(3) 0.008(2) C1 0.054(3) 0.037(3) 0.047(3) 0.010(2) 0.007(3) 0.003(3) C2 0.064(4) 0.042(3) 0.043(3) -0.001(2) 0.004(3) -0.002(3) C3 0.049(3) 0.028(3) 0.049(3) -0.005(2) 0.003(2) 0.001(2) C4 0.048(3) 0.050(4) 0.068(4) -0.007(3) -0.001(3) 0.012(3) C5 0.032(3) 0.054(4) 0.096(5) -0.007(4) 0.004(3) 0.005(3) C6 0.048(3) 0.048(3) 0.078(4) -0.020(3) 0.027(3) -0.008(3) C7 0.044(3) 0.033(3) 0.056(3) -0.008(2) 0.023(3) 0.002(2) C8 0.032(3) 0.036(3) 0.049(3) -0.003(2) 0.009(2) -0.002(2) C9 0.057(4) 0.043(3) 0.060(4) 0.006(3) 0.026(3) 0.012(3) C10 0.055(4) 0.036(3) 0.046(3) 0.007(2) 0.020(3) 0.007(3) C11 0.037(3) 0.045(3) 0.052(3) -0.008(3) -0.004(2) 0.007(2) C12 0.043(3) 0.032(3) 0.052(3) -0.004(2) 0.000(2) 0.010(2) C13 0.033(3) 0.034(3) 0.042(3) 0.008(2) 0.011(2) 0.006(2) C14 0.041(3) 0.044(3) 0.040(3) 0.001(2) 0.004(2) 0.003(2) C15 0.037(3) 0.034(3) 0.049(3) 0.000(2) 0.008(2) 0.008(2) C16 0.036(3) 0.049(3) 0.050(3) -0.001(3) 0.005(2) 0.007(2) C17 0.052(4) 0.069(4) 0.067(4) 0.015(3) 0.022(3) 0.010(3) C18 0.060(4) 0.092(5) 0.073(5) 0.011(4) 0.038(4) -0.004(4) C19 0.077(4) 0.053(4) 0.051(4) 0.004(3) 0.025(3) -0.004(3) C20 0.076(4) 0.064(4) 0.050(4) 0.021(3) 0.010(3) 0.003(3) C21 0.044(3) 0.065(4) 0.059(4) 0.009(3) 0.011(3) -0.003(3) C22 0.119(6) 0.076(5) 0.073(5) -0.004(4) 0.054(5) -0.025(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 O4 1.935(4) 1_545 ? Zn1 O2 1.977(4) . ? Zn1 N2 2.046(4) . ? Zn1 N1 2.070(4) . ? O1 C1 1.240(6) . ? O2 C1 1.251(7) . ? O3 C10 1.251(6) . ? O4 C10 1.268(7) . ? O4 Zn1 1.935(4) 1_565 ? N1 C15 1.328(6) . ? N1 C11 1.333(6) . ? N2 C21 1.329(7) . ? N2 C17 1.332(7) . ? O5 H5C 0.8200 . ? O5 H5D 0.8200 . ? O6 H6D 0.8200 . ? O6 H6C 0.8201 . ? C1 C2 1.504(8) . ? C2 C3 1.528(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.385(8) . ? C3 C8 1.392(7) . ? C4 C5 1.351(9) . ? C4 H4 0.9300 . ? C5 C6 1.371(9) . ? C5 H5 0.9300 . ? C6 C7 1.405(8) . ? C6 H6 0.9300 . ? C7 C8 1.373(7) . ? C7 C9 1.506(7) . ? C8 H8 0.9300 . ? C9 C10 1.510(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.362(7) . ? C11 H11 0.9300 . ? C12 C13 1.375(7) . ? C12 H12 0.9300 . ? C13 C14 1.389(7) . ? C13 C16 1.510(7) . ? C14 C15 1.378(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C16 1.508(10) 2_575 ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.386(8) . ? C17 H17 0.9300 . ? C18 C19 1.375(9) . ? C18 H18 0.9300 . ? C19 C20 1.387(9) . ? C19 C22 1.489(8) . ? C20 C21 1.375(8) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C22 1.489(14) 2_666 ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 O2 110.76(16) 1_545 . ? O4 Zn1 N2 112.72(17) 1_545 . ? O2 Zn1 N2 112.35(18) . . ? O4 Zn1 N1 122.68(17) 1_545 . ? O2 Zn1 N1 95.45(16) . . ? N2 Zn1 N1 101.57(16) . . ? C1 O2 Zn1 115.0(3) . . ? C10 O4 Zn1 111.2(3) . 1_565 ? C15 N1 C11 117.3(4) . . ? C15 N1 Zn1 125.6(3) . . ? C11 N1 Zn1 116.1(3) . . ? C21 N2 C17 117.3(5) . . ? C21 N2 Zn1 120.6(4) . . ? C17 N2 Zn1 122.1(4) . . ? H5C O5 H5D 96.5 . . ? H6D O6 H6C 109.8 . . ? O1 C1 O2 122.7(5) . . ? O1 C1 C2 120.4(5) . . ? O2 C1 C2 116.8(5) . . ? C1 C2 C3 112.5(5) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C8 117.7(5) . . ? C4 C3 C2 121.7(5) . . ? C8 C3 C2 120.7(5) . . ? C5 C4 C3 121.6(6) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 120.7(6) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C7 119.7(6) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 118.5(5) . . ? C8 C7 C9 122.1(5) . . ? C6 C7 C9 119.4(5) . . ? C7 C8 C3 121.8(5) . . ? C7 C8 H8 119.1 . . ? C3 C8 H8 119.1 . . ? C10 C9 C7 113.0(4) . . ? C10 C9 H9A 109.0 . . ? C7 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C7 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? O3 C10 O4 123.2(5) . . ? O3 C10 C9 120.2(5) . . ? O4 C10 C9 116.6(5) . . ? N1 C11 C12 123.4(5) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 120.2(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 116.4(5) . . ? C12 C13 C16 124.0(5) . . ? C14 C13 C16 119.6(5) . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? N1 C15 C14 122.4(5) . . ? N1 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C16 C16 C13 116.1(6) 2_575 . ? C16 C16 H16A 108.3 2_575 . ? C13 C16 H16A 108.3 . . ? C16 C16 H16B 108.3 2_575 . ? C13 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? N2 C17 C18 122.1(6) . . ? N2 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 121.3(6) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 115.5(6) . . ? C18 C19 C22 121.0(7) . . ? C20 C19 C22 123.5(7) . . ? C21 C20 C19 120.5(6) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? N2 C21 C20 123.3(6) . . ? N2 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? C19 C22 C22 113.8(8) . 2_666 ? C19 C22 H22A 108.8 . . ? C22 C22 H22A 108.8 2_666 . ? C19 C22 H22B 108.8 . . ? C22 C22 H22B 108.8 2_666 . ? H22A C22 H22B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O2 C1 -72.5(4) 1_545 . . . ? N2 Zn1 O2 C1 54.6(4) . . . . ? N1 Zn1 O2 C1 159.5(4) . . . . ? O4 Zn1 N1 C15 41.0(5) 1_545 . . . ? O2 Zn1 N1 C15 159.9(4) . . . . ? N2 Zn1 N1 C15 -85.9(4) . . . . ? O4 Zn1 N1 C11 -150.6(4) 1_545 . . . ? O2 Zn1 N1 C11 -31.7(4) . . . . ? N2 Zn1 N1 C11 82.5(4) . . . . ? O4 Zn1 N2 C21 29.6(5) 1_545 . . . ? O2 Zn1 N2 C21 -96.4(5) . . . . ? N1 Zn1 N2 C21 162.7(4) . . . . ? O4 Zn1 N2 C17 -150.2(5) 1_545 . . . ? O2 Zn1 N2 C17 83.8(5) . . . . ? N1 Zn1 N2 C17 -17.1(5) . . . . ? Zn1 O2 C1 O1 7.2(8) . . . . ? Zn1 O2 C1 C2 -173.3(4) . . . . ? O1 C1 C2 C3 113.4(6) . . . . ? O2 C1 C2 C3 -66.1(7) . . . . ? C1 C2 C3 C4 -86.7(6) . . . . ? C1 C2 C3 C8 91.9(6) . . . . ? C8 C3 C4 C5 1.0(8) . . . . ? C2 C3 C4 C5 179.6(5) . . . . ? C3 C4 C5 C6 -0.7(9) . . . . ? C4 C5 C6 C7 -0.1(9) . . . . ? C5 C6 C7 C8 0.5(8) . . . . ? C5 C6 C7 C9 -179.0(5) . . . . ? C6 C7 C8 C3 -0.1(7) . . . . ? C9 C7 C8 C3 179.4(5) . . . . ? C4 C3 C8 C7 -0.6(8) . . . . ? C2 C3 C8 C7 -179.2(4) . . . . ? C8 C7 C9 C10 47.4(7) . . . . ? C6 C7 C9 C10 -133.1(5) . . . . ? Zn1 O4 C10 O3 2.7(7) 1_565 . . . ? Zn1 O4 C10 C9 -177.1(3) 1_565 . . . ? C7 C9 C10 O3 -96.5(6) . . . . ? C7 C9 C10 O4 83.3(6) . . . . ? C15 N1 C11 C12 2.4(8) . . . . ? Zn1 N1 C11 C12 -167.0(4) . . . . ? N1 C11 C12 C13 -0.9(9) . . . . ? C11 C12 C13 C14 -1.4(8) . . . . ? C11 C12 C13 C16 177.6(5) . . . . ? C12 C13 C14 C15 2.1(7) . . . . ? C16 C13 C14 C15 -176.9(5) . . . . ? C11 N1 C15 C14 -1.7(7) . . . . ? Zn1 N1 C15 C14 166.6(4) . . . . ? C13 C14 C15 N1 -0.6(8) . . . . ? C12 C13 C16 C16 1.4(9) . . . 2_575 ? C14 C13 C16 C16 -179.6(6) . . . 2_575 ? C21 N2 C17 C18 0.9(10) . . . . ? Zn1 N2 C17 C18 -179.3(5) . . . . ? N2 C17 C18 C19 0.2(11) . . . . ? C17 C18 C19 C20 -0.7(10) . . . . ? C17 C18 C19 C22 177.8(6) . . . . ? C18 C19 C20 C21 0.0(10) . . . . ? C22 C19 C20 C21 -178.4(6) . . . . ? C17 N2 C21 C20 -1.7(9) . . . . ? Zn1 N2 C21 C20 178.6(5) . . . . ? C19 C20 C21 N2 1.2(10) . . . . ? C18 C19 C22 C22 -81.0(12) . . . 2_666 ? C20 C19 C22 C22 97.4(12) . . . 2_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6C O1 0.82 2.12 2.943(18) 175.9 2_666 O6 H6D O5 0.82 2.17 2.99(2) 178.4 . O5 H5D O1 0.82 2.25 3.07(2) 178.6 2_766 O5 H5C O5 0.82 1.74 2.56(4) 177.1 2_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.265 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.115 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 729345' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N2 O5 Zn' _chemical_formula_sum 'C21 H20 N2 O5 Zn' _chemical_formula_weight 445.76 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.562(4) _cell_length_b 10.592(2) _cell_length_c 10.940(2) _cell_angle_alpha 115.892(4) _cell_angle_beta 105.631(5) _cell_angle_gamma 95.654(5) _cell_volume 929.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 521 _cell_measurement_theta_min 2.208 _cell_measurement_theta_max 18.826 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 1.359 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6125 _exptl_absorpt_correction_T_max 0.8221 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_% 0 _diffrn_reflns_number 4608 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.1365 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3177 _reflns_number_gt 1785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Brucker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Brucker 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^)+(0.0608P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3177 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 O4 O 0.8555(5) 0.9586(5) 0.2490(5) 0.0497(14) Uani 1 1 d . . . O3 O 0.6921(5) 0.8329(5) 0.2876(5) 0.0485(14) Uani 1 1 d . . . N2 N 0.6140(6) 0.7596(5) 0.9698(5) 0.0294(13) Uani 1 1 d . . . C18 C 0.7120(8) 0.7643(7) 0.9038(7) 0.0366(18) Uani 1 1 d . . . H18 H 0.7778 0.8527 0.9379 0.044 Uiso 1 1 calc R . . C17 C 0.7200(7) 0.6446(7) 0.7881(7) 0.0356(18) Uani 1 1 d . . . H17 H 0.7887 0.6531 0.7444 0.043 Uiso 1 1 calc R . . C19 C 0.5257(7) 0.6305(7) 0.9204(7) 0.0351(18) Uani 1 1 d . . . H19 H 0.4582 0.6252 0.9663 0.042 Uiso 1 1 calc R . . C20 C 0.5257(7) 0.5041(7) 0.8068(7) 0.0350(17) Uani 1 1 d . . . H20 H 0.4612 0.4167 0.7779 0.042 Uiso 1 1 calc R . . C16 C 0.6244(7) 0.5106(7) 0.7367(6) 0.0306(17) Uani 1 1 d . . . Zn1 Zn 0.62275(9) -0.04474(8) 0.16027(8) 0.0334(3) Uani 1 1 d . . . O1 O 0.6725(6) 0.0860(5) 0.0785(5) 0.0562(15) Uani 1 1 d . . . O2 O 0.5966(5) 0.1055(5) -0.1227(5) 0.0371(12) Uani 1 1 d . . . N1 N 0.6358(6) 0.1434(6) 0.3579(5) 0.0321(14) Uani 1 1 d . . . C14 C 0.6151(7) 0.2444(7) 0.5956(7) 0.0394(18) Uani 1 1 d . . . H14 H 0.6024 0.2285 0.6695 0.047 Uiso 1 1 calc R . . C15 C 0.6191(7) 0.1302(7) 0.4705(7) 0.0383(18) Uani 1 1 d . . . H15 H 0.6097 0.0391 0.4642 0.046 Uiso 1 1 calc R . . C12 C 0.6503(8) 0.3954(7) 0.4932(7) 0.0416(19) Uani 1 1 d . . . H12 H 0.6636 0.4855 0.4974 0.050 Uiso 1 1 calc R . . C1 C 0.6958(8) 0.1189(6) -0.0117(8) 0.0342(17) Uani 1 1 d . . . C8 C 0.8583(8) 0.4384(7) 0.0433(7) 0.0406(19) Uani 1 1 d . . . H8 H 0.8285 0.3954 -0.0571 0.049 Uiso 1 1 calc R . . C13 C 0.6300(7) 0.3822(7) 0.6098(7) 0.0327(17) Uani 1 1 d . . . C9 C 0.9485(8) 0.8167(7) 0.3605(7) 0.0423(19) Uani 1 1 d . . . H9A H 1.0436 0.8625 0.3643 0.051 Uiso 1 1 calc R . . H9B H 0.9550 0.8432 0.4591 0.051 Uiso 1 1 calc R . . C7 C 0.8775(8) 0.5846(7) 0.1224(7) 0.0421(19) Uani 1 1 d . . . H7 H 0.8616 0.6389 0.0746 0.051 Uiso 1 1 calc R . . C3 C 0.8819(7) 0.3536(7) 0.1088(7) 0.0329(17) Uani 1 1 d . . . C2 C 0.8586(7) 0.1929(7) 0.0209(8) 0.0420(19) Uani 1 1 d . . . H2A H 0.9282 0.1588 0.0746 0.050 Uiso 1 1 calc R . . H2B H 0.8761 0.1696 -0.0689 0.050 Uiso 1 1 calc R . . C5 C 0.9442(8) 0.5694(8) 0.3394(7) 0.046(2) Uani 1 1 d . . . H5 H 0.9736 0.6117 0.4398 0.056 Uiso 1 1 calc R . . C4 C 0.9247(8) 0.4207(8) 0.2576(8) 0.0440(19) Uani 1 1 d . . . H4 H 0.9410 0.3655 0.3045 0.053 Uiso 1 1 calc R . . C6 C 0.9208(7) 0.6550(7) 0.2745(7) 0.0363(18) Uani 1 1 d . . . C11 C 0.6506(8) 0.2754(7) 0.3727(7) 0.0423(19) Uani 1 1 d . . . H11 H 0.6619 0.2879 0.2966 0.051 Uiso 1 1 calc R . . C21 C 0.2370(10) 0.1330(10) 0.3616(10) 0.073(3) Uani 1 1 d . . . H21A H 0.3170 0.1839 0.3503 0.109 Uiso 1 1 calc R . . H21B H 0.2380 0.0326 0.3233 0.109 Uiso 1 1 calc R . . H21C H 0.2501 0.1739 0.4627 0.109 Uiso 1 1 calc R . . O5 O 0.1031(6) 0.1449(8) 0.2887(9) 0.099(3) Uani 1 1 d . . . H5A H 0.0349 0.1037 0.3007 0.149 Uiso 1 1 calc R . . C10 C 0.8261(8) 0.8715(7) 0.2956(7) 0.0373(18) 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 O4 0.050(3) 0.030(3) 0.056(3) 0.016(3) 0.011(3) 0.004(2) O3 0.040(3) 0.045(3) 0.049(3) 0.014(3) 0.016(3) 0.007(3) N2 0.031(3) 0.026(3) 0.029(3) 0.011(3) 0.011(3) 0.004(3) C18 0.043(4) 0.026(4) 0.029(4) 0.007(3) 0.010(3) -0.003(3) C17 0.027(4) 0.040(4) 0.035(4) 0.016(4) 0.010(3) 0.003(3) C19 0.042(4) 0.029(4) 0.031(4) 0.008(3) 0.020(3) 0.005(3) C20 0.036(4) 0.028(4) 0.034(4) 0.010(3) 0.013(3) 0.005(3) C16 0.044(4) 0.023(4) 0.022(4) 0.009(3) 0.011(3) 0.009(3) Zn1 0.0360(5) 0.0283(5) 0.0287(5) 0.0090(4) 0.0096(3) 0.0056(3) O1 0.097(4) 0.035(3) 0.043(3) 0.021(3) 0.032(3) 0.013(3) O2 0.029(3) 0.055(3) 0.029(3) 0.023(2) 0.009(2) 0.010(2) N1 0.036(3) 0.029(3) 0.024(3) 0.008(3) 0.009(3) 0.004(3) C14 0.046(5) 0.034(4) 0.034(4) 0.013(4) 0.016(3) 0.008(3) C15 0.046(4) 0.025(4) 0.038(4) 0.008(3) 0.021(3) 0.003(3) C12 0.057(5) 0.025(4) 0.038(4) 0.010(3) 0.019(4) 0.012(3) C1 0.044(4) 0.014(3) 0.041(4) 0.004(3) 0.023(4) 0.011(3) C8 0.051(5) 0.037(4) 0.030(4) 0.015(4) 0.011(3) 0.007(4) C13 0.031(4) 0.029(4) 0.028(4) 0.007(3) 0.009(3) -0.002(3) C9 0.043(4) 0.033(4) 0.032(4) 0.009(3) -0.003(3) 0.008(3) C7 0.062(5) 0.031(4) 0.036(4) 0.019(4) 0.015(4) 0.012(4) C3 0.026(4) 0.024(4) 0.041(4) 0.010(3) 0.013(3) 0.001(3) C2 0.039(4) 0.033(4) 0.046(4) 0.016(4) 0.007(3) 0.010(3) C5 0.058(5) 0.040(5) 0.026(4) 0.011(4) 0.002(3) 0.012(4) C4 0.047(5) 0.040(5) 0.041(5) 0.020(4) 0.007(4) 0.012(4) C6 0.031(4) 0.033(4) 0.037(4) 0.013(3) 0.008(3) 0.007(3) C11 0.062(5) 0.030(4) 0.034(4) 0.015(4) 0.017(4) 0.010(4) C21 0.069(6) 0.076(7) 0.079(7) 0.048(6) 0.019(5) 0.007(5) O5 0.053(4) 0.132(7) 0.146(7) 0.110(6) 0.015(4) 0.005(4) C10 0.052(5) 0.013(4) 0.027(4) -0.002(3) 0.007(3) 0.001(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 O4 C10 1.275(8) . ? O4 Zn1 2.165(5) 1_565 ? O3 C10 1.274(8) . ? O3 Zn1 2.304(5) 1_565 ? N2 C19 1.325(8) . ? N2 C18 1.337(8) . ? N2 Zn1 2.178(5) 1_566 ? C18 C17 1.373(9) . ? C18 H18 0.9300 . ? C17 C16 1.392(8) . ? C17 H17 0.9300 . ? C19 C20 1.373(9) . ? C19 H19 0.9300 . ? C20 C16 1.380(9) . ? C20 H20 0.9300 . ? C16 C13 1.479(8) . ? Zn1 O2 2.005(4) 2_655 ? Zn1 O1 2.031(5) . ? Zn1 O4 2.165(5) 1_545 ? Zn1 N1 2.168(5) . ? Zn1 N2 2.178(5) 1_544 ? Zn1 O3 2.304(5) 1_545 ? Zn1 C10 2.588(7) 1_545 ? O1 C1 1.245(8) . ? O2 C1 1.264(8) . ? O2 Zn1 2.005(4) 2_655 ? N1 C11 1.325(8) . ? N1 C15 1.347(8) . ? C14 C13 1.387(9) . ? C14 C15 1.389(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C12 C11 1.375(9) . ? C12 C13 1.403(9) . ? C12 H12 0.9300 . ? C1 C2 1.542(9) . ? C8 C7 1.367(9) . ? C8 C3 1.373(9) . ? C8 H8 0.9300 . ? C9 C6 1.503(9) . ? C9 C10 1.502(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 C6 1.407(9) . ? C7 H7 0.9300 . ? C3 C4 1.377(9) . ? C3 C2 1.501(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C5 C6 1.376(9) . ? C5 C4 1.392(9) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C11 H11 0.9300 . ? C21 O5 1.365(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O5 H5A 0.8200 . ? C10 Zn1 2.588(7) 1_565 ? 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 C10 O4 Zn1 94.0(4) . 1_565 ? C10 O3 Zn1 87.7(4) . 1_565 ? C19 N2 C18 116.3(6) . . ? C19 N2 Zn1 124.3(5) . 1_566 ? C18 N2 Zn1 119.1(4) . 1_566 ? N2 C18 C17 123.1(6) . . ? N2 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? C18 C17 C16 119.5(6) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? N2 C19 C20 125.3(7) . . ? N2 C19 H19 117.4 . . ? C20 C19 H19 117.4 . . ? C19 C20 C16 118.0(6) . . ? C19 C20 H20 121.0 . . ? C16 C20 H20 121.0 . . ? C20 C16 C17 117.8(6) . . ? C20 C16 C13 122.6(6) . . ? C17 C16 C13 119.7(6) . . ? O2 Zn1 O1 114.1(2) 2_655 . ? O2 Zn1 O4 152.97(19) 2_655 1_545 ? O1 Zn1 O4 93.0(2) . 1_545 ? O2 Zn1 N1 87.54(19) 2_655 . ? O1 Zn1 N1 90.0(2) . . ? O4 Zn1 N1 92.39(19) 1_545 . ? O2 Zn1 N2 92.78(19) 2_655 1_544 ? O1 Zn1 N2 93.1(2) . 1_544 ? O4 Zn1 N2 85.70(18) 1_545 1_544 ? N1 Zn1 N2 176.4(2) . 1_544 ? O2 Zn1 O3 94.17(18) 2_655 1_545 ? O1 Zn1 O3 151.8(2) . 1_545 ? O4 Zn1 O3 58.80(18) 1_545 1_545 ? N1 Zn1 O3 90.26(19) . 1_545 ? N2 Zn1 O3 86.16(18) 1_544 1_545 ? O2 Zn1 C10 123.6(2) 2_655 1_545 ? O1 Zn1 C10 122.4(2) . 1_545 ? O4 Zn1 C10 29.44(19) 1_545 1_545 ? N1 Zn1 C10 93.3(2) . 1_545 ? N2 Zn1 C10 83.50(19) 1_544 1_545 ? O3 Zn1 C10 29.47(18) 1_545 1_545 ? C1 O1 Zn1 157.7(4) . . ? C1 O2 Zn1 121.8(4) . 2_655 ? C11 N1 C15 115.8(6) . . ? C11 N1 Zn1 122.9(5) . . ? C15 N1 Zn1 121.1(4) . . ? C13 C14 C15 119.8(7) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? N1 C15 C14 124.0(7) . . ? N1 C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? C11 C12 C13 120.2(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? O1 C1 O2 125.6(6) . . ? O1 C1 C2 117.1(6) . . ? O2 C1 C2 117.1(6) . . ? C7 C8 C3 121.5(6) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C14 C13 C12 115.8(6) . . ? C14 C13 C16 124.2(6) . . ? C12 C13 C16 120.0(6) . . ? C6 C9 C10 111.8(5) . . ? C6 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C6 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C8 C7 C6 121.6(7) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C8 C3 C4 117.7(6) . . ? C8 C3 C2 121.1(6) . . ? C4 C3 C2 121.1(6) . . ? C3 C2 C1 108.3(6) . . ? C3 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? C3 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C6 C5 C4 121.2(7) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C3 C4 C5 121.3(7) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C5 C6 C7 116.6(6) . . ? C5 C6 C9 122.3(6) . . ? C7 C6 C9 121.0(6) . . ? N1 C11 C12 124.4(7) . . ? N1 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C21 O5 H5A 109.5 . . ? O3 C10 O4 119.1(7) . . ? O3 C10 C9 120.5(6) . . ? O4 C10 C9 120.4(7) . . ? O3 C10 Zn1 62.8(4) . 1_565 ? O4 C10 Zn1 56.6(4) . 1_565 ? C9 C10 Zn1 174.2(5) . 1_565 ? 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 C19 N2 C18 C17 2.0(10) . . . . ? Zn1 N2 C18 C17 176.4(5) 1_566 . . . ? N2 C18 C17 C16 -1.1(11) . . . . ? C18 N2 C19 C20 -1.2(10) . . . . ? Zn1 N2 C19 C20 -175.2(5) 1_566 . . . ? N2 C19 C20 C16 -0.5(11) . . . . ? C19 C20 C16 C17 1.4(10) . . . . ? C19 C20 C16 C13 -177.7(6) . . . . ? C18 C17 C16 C20 -0.7(10) . . . . ? C18 C17 C16 C13 178.4(6) . . . . ? O2 Zn1 O1 C1 -90.5(14) 2_655 . . . ? O4 Zn1 O1 C1 89.8(14) 1_545 . . . ? N1 Zn1 O1 C1 -177.8(14) . . . . ? N2 Zn1 O1 C1 4.0(14) 1_544 . . . ? O3 Zn1 O1 C1 91.6(14) 1_545 . . . ? C10 Zn1 O1 C1 88.2(14) 1_545 . . . ? O2 Zn1 N1 C11 -106.2(5) 2_655 . . . ? O1 Zn1 N1 C11 7.8(6) . . . . ? O4 Zn1 N1 C11 100.8(5) 1_545 . . . ? N2 Zn1 N1 C11 158(3) 1_544 . . . ? O3 Zn1 N1 C11 159.6(5) 1_545 . . . ? C10 Zn1 N1 C11 130.3(5) 1_545 . . . ? O2 Zn1 N1 C15 69.2(5) 2_655 . . . ? O1 Zn1 N1 C15 -176.7(5) . . . . ? O4 Zn1 N1 C15 -83.7(5) 1_545 . . . ? N2 Zn1 N1 C15 -26(4) 1_544 . . . ? O3 Zn1 N1 C15 -24.9(5) 1_545 . . . ? C10 Zn1 N1 C15 -54.2(5) 1_545 . . . ? C11 N1 C15 C14 0.8(10) . . . . ? Zn1 N1 C15 C14 -175.0(5) . . . . ? C13 C14 C15 N1 -0.6(11) . . . . ? Zn1 O1 C1 O2 75.1(17) . . . . ? Zn1 O1 C1 C2 -109.7(13) . . . . ? Zn1 O2 C1 O1 6.2(9) 2_655 . . . ? Zn1 O2 C1 C2 -169.0(4) 2_655 . . . ? C15 C14 C13 C12 -0.7(10) . . . . ? C15 C14 C13 C16 178.8(6) . . . . ? C11 C12 C13 C14 1.7(10) . . . . ? C11 C12 C13 C16 -177.8(6) . . . . ? C20 C16 C13 C14 -39.3(10) . . . . ? C17 C16 C13 C14 141.6(7) . . . . ? C20 C16 C13 C12 140.1(7) . . . . ? C17 C16 C13 C12 -39.0(9) . . . . ? C3 C8 C7 C6 -0.7(11) . . . . ? C7 C8 C3 C4 0.5(10) . . . . ? C7 C8 C3 C2 179.2(6) . . . . ? C8 C3 C2 C1 -92.0(8) . . . . ? C4 C3 C2 C1 86.7(8) . . . . ? O1 C1 C2 C3 -89.0(7) . . . . ? O2 C1 C2 C3 86.6(7) . . . . ? C8 C3 C4 C5 -0.3(10) . . . . ? C2 C3 C4 C5 -179.0(6) . . . . ? C6 C5 C4 C3 0.3(11) . . . . ? C4 C5 C6 C7 -0.4(11) . . . . ? C4 C5 C6 C9 -176.8(7) . . . . ? C8 C7 C6 C5 0.7(11) . . . . ? C8 C7 C6 C9 177.1(7) . . . . ? C10 C9 C6 C5 -137.4(7) . . . . ? C10 C9 C6 C7 46.3(9) . . . . ? C15 N1 C11 C12 0.3(10) . . . . ? Zn1 N1 C11 C12 176.0(5) . . . . ? C13 C12 C11 N1 -1.6(11) . . . . ? Zn1 O3 C10 O4 6.2(6) 1_565 . . . ? Zn1 O3 C10 C9 -174.5(5) 1_565 . . . ? Zn1 O4 C10 O3 -6.6(6) 1_565 . . . ? Zn1 O4 C10 C9 174.1(5) 1_565 . . . ? C6 C9 C10 O3 63.1(8) . . . . ? C6 C9 C10 O4 -117.6(7) . . . . ? C6 C9 C10 Zn1 -61(5) . . . 1_565 ? 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 O5 H5A O4 0.82 1.96 2.732(7) 157.7 1_445 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 1.178 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.118