# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_block _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- Mat_dep.cif' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. Rosa Carballo' _publ_contact_author_address ; Departamento de Qu\'imica Inorg\'anica Facultade de Qu\'imica, Centro de Ciencias Experimentais Universidade de Vigo E-36310 Vigo Galicia, Spain ; _publ_contact_author_email rcrial@uvigo.es # =================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Mononuclear discrete complexes and coordination polymers based on metal(II) chelidonate complexes with aromatic N,N-chelating ligands ; loop_ _publ_author_name _publ_author_address A.B.Lago ; Departamento de Qu\'imica Inorg\'anica Facultade de Qu\'imica Universidade de Vigo 36310-Vigo, Galicia Spain ; A.Hagenbach ; Institut fur Chemie und Biochemie Freie Universitat Berlin D14195-Berlin Germany ; R.Carballo ; Departamento de Qu\'imica Inorg\'anica Facultade de Ciencias-Qu\'imica Universidade de Vigo 36310-Vigo, Galicia Spain ; N.Fernandez-Hermida ; Departamento de Qu\'imica Inorg\'anica Facultade de Ciencias-Qu\'imica Universidade de Vigo 36310-Vigo, Galicia Spain ; ; E.M.Vazquez-Lopez ; ; Departamento de Qu\'imica Inorg\'anica Facultade de Ciencias-Qu\'imica Universidade de Vigo 36310-Vigo, Galicia Spain ; #============================================ data_1 _database_code_depnum_ccdc_archive 'CCDC 779941' #TrackingRef '- Mat_dep.cif' ################ # CCDC 779941 # ################ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 Cu N2 O6' _chemical_formula_weight 401.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.6342(14) _cell_length_b 12.1379(17) _cell_length_c 13.3493(19) _cell_angle_alpha 90.00 _cell_angle_beta 104.034(2) _cell_angle_gamma 90.00 _cell_volume 1514.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 1.483 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.607355 _exptl_absorpt_correction_T_max 1.000000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9331 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.07 _reflns_number_total 3569 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 3569 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_restrained_S_all 0.873 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.35350(5) 0.97815(4) 0.54270(4) 0.02767(18) Uani 1 1 d . . . O1 O 0.5048(3) 0.8076(2) 0.9040(2) 0.0299(6) Uani 1 1 d . . . O3 O 0.7681(4) 1.0607(3) 1.0269(3) 0.0666(12) Uani 1 1 d . . . O4 O 0.4375(4) 0.9823(2) 0.6876(2) 0.0382(7) Uani 1 1 d . . . O5 O 0.3312(4) 0.8243(3) 0.7124(3) 0.0548(9) Uani 1 1 d . . . O6 O 0.4852(3) 0.6266(2) 1.0061(2) 0.0320(7) Uani 1 1 d . . . O7 O 0.6336(4) 0.6932(3) 1.1501(2) 0.0458(8) Uani 1 1 d . . . C1 C 0.5144(4) 0.9005(3) 0.8475(3) 0.0304(9) Uani 1 1 d . . . C2 C 0.5996(5) 0.9854(4) 0.8858(3) 0.0342(10) Uani 1 1 d . . . H2 H 0.6007 1.0469 0.8445 0.041 Uiso 1 1 calc R . . C3 C 0.6894(5) 0.9838(4) 0.9891(4) 0.0396(10) Uani 1 1 d . . . C4 C 0.6752(4) 0.8833(3) 1.0448(3) 0.0343(10) Uani 1 1 d . . . H4 H 0.7299 0.8745 1.1120 0.041 Uiso 1 1 calc R . . C5 C 0.5859(4) 0.8038(3) 1.0017(3) 0.0268(8) Uani 1 1 d . . . C11 C 0.4170(5) 0.8987(4) 0.7404(3) 0.0346(10) Uani 1 1 d . . . C51 C 0.5667(4) 0.6991(3) 1.0609(3) 0.0300(9) Uani 1 1 d . . . N1 N 0.2138(4) 1.0947(3) 0.5540(3) 0.0302(8) Uani 1 1 d . . . N2 N 0.2248(4) 0.9656(3) 0.4018(3) 0.0310(8) Uani 1 1 d . . . C12 C 0.2232(5) 1.1611(3) 0.6360(3) 0.0363(10) Uani 1 1 d . . . H12 H 0.3013 1.1540 0.6924 0.044 Uiso 1 1 calc R . . C13 C 0.1207(5) 1.2392(4) 0.6392(4) 0.0455(12) Uani 1 1 d . . . H13 H 0.1300 1.2853 0.6961 0.055 Uiso 1 1 calc R . . C14 C 0.0042(6) 1.2476(4) 0.5562(4) 0.0516(13) Uani 1 1 d . . . H14 H -0.0676 1.2984 0.5576 0.062 Uiso 1 1 calc R . . C15 C -0.0065(5) 1.1811(4) 0.4709(4) 0.0442(11) Uani 1 1 d . . . H15 H -0.0848 1.1865 0.4145 0.053 Uiso 1 1 calc R . . C16 C 0.1020(4) 1.1061(3) 0.4711(3) 0.0313(9) Uani 1 1 d . . . C17 C 0.1096(4) 1.0338(3) 0.3829(3) 0.0317(9) Uani 1 1 d . . . C18 C 0.0123(5) 1.0361(4) 0.2888(4) 0.0401(11) Uani 1 1 d . . . H18 H -0.0675 1.0817 0.2779 0.048 Uiso 1 1 calc R . . C19 C 0.0356(5) 0.9687(4) 0.2099(4) 0.0450(12) Uani 1 1 d . . . H19 H -0.0269 0.9706 0.1448 0.054 Uiso 1 1 calc R . . C20 C 0.1513(5) 0.8998(4) 0.2293(4) 0.0422(11) Uani 1 1 d . . . H20 H 0.1671 0.8532 0.1779 0.051 Uiso 1 1 calc R . . C21 C 0.2451(5) 0.8998(4) 0.3265(3) 0.0369(10) Uani 1 1 d . . . H21 H 0.3238 0.8530 0.3393 0.044 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 Cu 0.0274(3) 0.0288(3) 0.0235(3) 0.0018(2) -0.00022(19) 0.0065(2) O1 0.0287(15) 0.0319(15) 0.0229(14) 0.0018(11) -0.0055(11) -0.0047(12) O3 0.072(3) 0.047(2) 0.059(2) 0.0181(18) -0.026(2) -0.033(2) O4 0.0496(19) 0.0338(16) 0.0273(15) 0.0054(13) 0.0016(14) 0.0115(14) O5 0.048(2) 0.068(2) 0.0375(19) 0.0079(17) -0.0113(16) -0.0226(18) O6 0.0354(16) 0.0306(15) 0.0261(15) 0.0004(11) 0.0000(13) -0.0120(12) O7 0.058(2) 0.0404(18) 0.0274(16) 0.0070(13) -0.0125(15) -0.0191(16) C1 0.031(2) 0.033(2) 0.025(2) 0.0054(16) 0.0029(17) 0.0011(17) C2 0.033(2) 0.034(2) 0.032(2) 0.0112(18) 0.0003(18) -0.0037(18) C3 0.036(2) 0.035(2) 0.041(3) 0.008(2) -0.003(2) -0.012(2) C4 0.033(2) 0.036(2) 0.026(2) 0.0044(18) -0.0083(18) -0.0069(18) C5 0.028(2) 0.030(2) 0.0190(18) 0.0010(15) -0.0008(16) -0.0016(16) C11 0.030(2) 0.044(3) 0.025(2) 0.0000(19) -0.0020(18) 0.0018(19) C51 0.030(2) 0.029(2) 0.029(2) 0.0009(17) 0.0008(17) -0.0035(17) N1 0.0263(18) 0.0303(18) 0.0320(19) 0.0021(14) 0.0034(15) 0.0046(14) N2 0.0270(18) 0.0313(19) 0.0312(19) 0.0005(15) 0.0001(15) 0.0017(14) C12 0.036(2) 0.033(2) 0.039(2) 0.0032(19) 0.008(2) 0.0056(19) C13 0.053(3) 0.036(3) 0.049(3) -0.004(2) 0.017(2) 0.014(2) C14 0.046(3) 0.039(3) 0.069(4) 0.002(3) 0.013(3) 0.021(2) C15 0.034(3) 0.040(3) 0.055(3) 0.010(2) 0.005(2) 0.014(2) C16 0.023(2) 0.031(2) 0.038(2) 0.0070(18) 0.0057(18) 0.0016(16) C17 0.025(2) 0.032(2) 0.034(2) 0.0075(18) -0.0019(17) -0.0011(17) C18 0.030(2) 0.040(3) 0.043(3) 0.013(2) -0.005(2) -0.0008(19) C19 0.039(3) 0.052(3) 0.033(2) 0.008(2) -0.013(2) -0.010(2) C20 0.038(3) 0.050(3) 0.033(2) -0.004(2) -0.002(2) -0.003(2) C21 0.034(2) 0.042(3) 0.031(2) -0.0022(19) 0.0006(19) 0.0018(19) _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 Cu O4 1.908(3) . ? Cu O6 1.940(3) 4_575 ? Cu N1 1.983(3) . ? Cu N2 1.992(4) . ? Cu O6 2.564(3) 2_656 ? O1 C5 1.349(4) . ? O1 C1 1.372(5) . ? O3 C3 1.231(5) . ? O4 C11 1.278(5) . ? O5 C11 1.220(5) . ? O6 C51 1.284(5) . ? O6 Cu 1.940(3) 4_576 ? O7 C51 1.210(5) . ? C1 C2 1.339(6) . ? C1 C11 1.509(6) . ? C2 C3 1.440(6) . ? C3 C4 1.452(6) . ? C4 C5 1.328(5) . ? C5 C51 1.531(5) . ? N1 C12 1.345(5) . ? N1 C16 1.351(5) . ? N2 C21 1.335(5) . ? N2 C17 1.358(5) . ? C12 C13 1.377(6) . ? C13 C14 1.376(7) . ? C14 C15 1.379(7) . ? C15 C16 1.385(6) . ? C16 C17 1.485(6) . ? C17 C18 1.374(6) . ? C18 C19 1.393(7) . ? C19 C20 1.368(7) . ? C20 C21 1.389(6) . ? 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 Cu O6 97.46(12) . 4_575 ? O4 Cu N1 91.91(13) . . ? O6 Cu N1 169.60(12) 4_575 . ? O4 Cu N2 166.75(14) . . ? O6 Cu N2 90.44(13) 4_575 . ? N1 Cu N2 81.23(14) . . ? O4 Cu O6 96.02(12) . 2_656 ? O6 Cu O6 85.56(11) 4_575 2_656 ? N1 Cu O6 88.99(12) . 2_656 ? N2 Cu O6 95.19(12) . 2_656 ? C5 O1 C1 117.3(3) . . ? C11 O4 Cu 117.0(3) . . ? C51 O6 Cu 130.7(2) . 4_576 ? C2 C1 O1 122.7(4) . . ? C2 C1 C11 123.8(4) . . ? O1 C1 C11 113.6(3) . . ? C1 C2 C3 121.7(4) . . ? O3 C3 C2 123.4(4) . . ? O3 C3 C4 123.5(4) . . ? C2 C3 C4 113.1(4) . . ? C5 C4 C3 121.4(4) . . ? C4 C5 O1 123.8(4) . . ? C4 C5 C51 121.8(4) . . ? O1 C5 C51 114.4(3) . . ? O5 C11 O4 127.1(4) . . ? O5 C11 C1 121.4(4) . . ? O4 C11 C1 111.5(4) . . ? O7 C51 O6 128.8(4) . . ? O7 C51 C5 117.0(4) . . ? O6 C51 C5 114.1(3) . . ? C12 N1 C16 119.2(4) . . ? C12 N1 Cu 125.2(3) . . ? C16 N1 Cu 115.6(3) . . ? C21 N2 C17 119.2(4) . . ? C21 N2 Cu 125.8(3) . . ? C17 N2 Cu 115.0(3) . . ? N1 C12 C13 122.0(4) . . ? C14 C13 C12 118.5(4) . . ? C13 C14 C15 120.3(4) . . ? C14 C15 C16 118.6(5) . . ? N1 C16 C15 121.3(4) . . ? N1 C16 C17 113.9(3) . . ? C15 C16 C17 124.7(4) . . ? N2 C17 C18 121.8(4) . . ? N2 C17 C16 114.1(4) . . ? C18 C17 C16 124.0(4) . . ? C17 C18 C19 118.7(4) . . ? C20 C19 C18 119.2(4) . . ? C19 C20 C21 119.5(4) . . ? N2 C21 C20 121.5(4) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.613 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.089 #============================================ data_2 _database_code_depnum_ccdc_archive 'CCDC 779942' #TrackingRef '- Mat_dep.cif' ################ # CCDC 779942 # ################ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H20 N4 O15 Zn2' _chemical_formula_weight 855.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.872(3) _cell_length_b 14.004(5) _cell_length_c 15.346(5) _cell_angle_alpha 71.070(6) _cell_angle_beta 73.666(7) _cell_angle_gamma 76.130(7) _cell_volume 1707.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1607 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 23.53 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.779955 _exptl_absorpt_correction_T_max 1.000000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7615 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5041 _reflns_number_gt 3311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^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 5041 _refine_ls_number_parameters 505 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.147 _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 0.96657(10) 0.26139(6) 0.35287(6) 0.0354(3) Uani 1 1 d . . . Zn2 Zn 0.63767(10) 0.23302(6) -0.21861(6) 0.0386(3) Uani 1 1 d . . . O1 O 1.3322(5) 0.1659(3) 0.5825(3) 0.0373(12) Uani 1 1 d . . . O3 O 1.4254(6) -0.1427(4) 0.6302(4) 0.0500(14) Uani 1 1 d . . . O4 O 1.5458(6) 0.1356(4) 0.7458(4) 0.0523(15) Uani 1 1 d . . . O5 O 1.5592(6) 0.2521(4) 0.6063(4) 0.0506(14) Uani 1 1 d . . . O6 O 1.0951(6) 0.1609(4) 0.4403(4) 0.0574(16) Uani 1 1 d . . . O7 O 1.0802(9) 0.2749(5) 0.5134(5) 0.097(3) Uani 1 1 d . . . O11 O 0.8157(5) 0.1858(3) 0.0838(3) 0.0332(12) Uani 1 1 d . . . O13 O 0.9129(6) -0.1257(4) 0.1715(4) 0.0476(14) Uani 1 1 d . . . O14 O 0.9478(6) 0.1650(4) 0.2852(3) 0.0472(14) Uani 1 1 d . . . O15 O 0.8551(7) 0.3021(4) 0.1794(4) 0.0540(15) Uani 1 1 d . . . O16 O 0.7005(6) 0.1421(4) -0.0988(3) 0.0484(14) Uani 1 1 d . . . O17 O 0.7234(7) 0.2857(4) -0.0750(4) 0.0526(15) Uani 1 1 d . . . N1 N 0.4135(7) 0.2934(5) -0.1453(5) 0.0470(17) Uani 1 1 d . . . N2 N 0.6237(7) 0.3909(5) -0.2810(4) 0.0375(15) Uani 1 1 d . . . N3 N 0.9165(7) 0.4208(4) 0.3305(4) 0.0347(15) Uani 1 1 d . . . N4 N 1.1643(7) 0.3143(5) 0.2470(5) 0.0492(18) Uani 1 1 d . . . C1 C 1.4368(8) 0.1079(5) 0.6353(5) 0.0312(17) Uani 1 1 d . . . C2 C 1.4685(8) 0.0058(6) 0.6547(5) 0.0391(18) Uani 1 1 d . . . H2 H 1.5397 -0.0310 0.6930 0.047 Uiso 1 1 calc R . . C3 C 1.3928(9) -0.0480(6) 0.6168(5) 0.0388(19) Uani 1 1 d . . . C4 C 1.2815(8) 0.0181(5) 0.5623(5) 0.0323(17) Uani 1 1 d . . . H4 H 1.2275 -0.0103 0.5356 0.039 Uiso 1 1 calc R . . C5 C 1.2537(8) 0.1175(5) 0.5492(5) 0.0276(16) Uani 1 1 d . . . C10 C 1.5215(9) 0.1717(6) 0.6643(6) 0.0401(19) Uani 1 1 d . . . C11 C 0.8734(8) 0.1368(5) 0.1630(5) 0.0305(16) Uani 1 1 d . . . C12 C 0.9080(8) 0.0352(6) 0.1931(5) 0.0369(18) Uani 1 1 d . . . H12 H 0.9499 0.0057 0.2467 0.044 Uiso 1 1 calc R . . C13 C 0.8822(8) -0.0304(6) 0.1447(5) 0.0347(17) Uani 1 1 d . . . C14 C 0.8181(8) 0.0256(5) 0.0622(5) 0.0357(18) Uani 1 1 d . . . H14 H 0.7956 -0.0106 0.0275 0.043 Uiso 1 1 calc R . . C15 C 0.7901(8) 0.1274(5) 0.0342(5) 0.0289(16) Uani 1 1 d . . . C51 C 1.1325(10) 0.1936(6) 0.4971(5) 0.0419(19) Uani 1 1 d . . . C110 C 0.8933(8) 0.2091(6) 0.2127(5) 0.0361(18) Uani 1 1 d . . . C151 C 0.7331(9) 0.1929(6) -0.0542(5) 0.0401(19) Uani 1 1 d . . . C21 C 0.3138(10) 0.2387(8) -0.0799(7) 0.068(3) Uani 1 1 d . . . H21 H 0.3347 0.1680 -0.0692 0.082 Uiso 1 1 calc R . . C22 C 0.1781(12) 0.2820(10) -0.0258(7) 0.081(3) Uani 1 1 d . . . H22 H 0.1096 0.2414 0.0210 0.098 Uiso 1 1 calc R . . C23 C 0.1478(12) 0.3862(9) -0.0433(8) 0.080(3) Uani 1 1 d . . . H23 H 0.0572 0.4172 -0.0083 0.096 Uiso 1 1 calc R . . C24 C 0.2492(11) 0.4443(7) -0.1113(7) 0.062(3) Uani 1 1 d . . . H24 H 0.2302 0.5150 -0.1222 0.075 Uiso 1 1 calc R . . C25 C 0.3825(9) 0.3969(6) -0.1646(6) 0.043(2) Uani 1 1 d . . . C26 C 0.4989(9) 0.4510(6) -0.2427(5) 0.0409(19) Uani 1 1 d . . . C27 C 0.4807(11) 0.5557(6) -0.2780(7) 0.056(2) Uani 1 1 d . . . H27 H 0.3924 0.5964 -0.2511 0.067 Uiso 1 1 calc R . . C28 C 0.5910(12) 0.5996(7) -0.3516(7) 0.060(3) Uani 1 1 d . . . H28 H 0.5804 0.6705 -0.3747 0.072 Uiso 1 1 calc R . . C29 C 0.7195(11) 0.5384(7) -0.3921(6) 0.055(2) Uani 1 1 d . . . H29 H 0.7967 0.5668 -0.4429 0.066 Uiso 1 1 calc R . . C30 C 0.7302(10) 0.4340(7) -0.3554(6) 0.052(2) Uani 1 1 d . . . H30 H 0.8148 0.3919 -0.3833 0.063 Uiso 1 1 calc R . . C31 C 1.2859(11) 0.2532(8) 0.2084(7) 0.073(3) Uani 1 1 d . . . H31 H 1.2889 0.1827 0.2313 0.087 Uiso 1 1 calc R . . C32 C 1.4079(11) 0.2910(10) 0.1351(8) 0.085(3) Uani 1 1 d . . . H32 H 1.4950 0.2470 0.1116 0.102 Uiso 1 1 calc R . . C33 C 1.3967(13) 0.3933(10) 0.0988(8) 0.088(3) Uani 1 1 d . . . H33 H 1.4741 0.4204 0.0473 0.106 Uiso 1 1 calc R . . C34 C 1.2728(11) 0.4578(8) 0.1370(7) 0.068(3) Uani 1 1 d . . . H34 H 1.2672 0.5283 0.1132 0.082 Uiso 1 1 calc R . . C35 C 1.1557(9) 0.4160(6) 0.2119(6) 0.045(2) Uani 1 1 d . . . C36 C 1.0199(9) 0.4748(6) 0.2612(5) 0.0405(19) Uani 1 1 d . . . C37 C 0.9906(11) 0.5819(6) 0.2411(6) 0.057(2) Uani 1 1 d . . . H37 H 1.0592 0.6203 0.1918 0.068 Uiso 1 1 calc R . . C38 C 0.8605(11) 0.6307(7) 0.2938(7) 0.061(3) Uani 1 1 d . . . H38 H 0.8425 0.7016 0.2808 0.073 Uiso 1 1 calc R . . C39 C 0.7590(11) 0.5745(7) 0.3648(7) 0.058(2) Uani 1 1 d . . . H39 H 0.6702 0.6055 0.4010 0.070 Uiso 1 1 calc R . . C40 C 0.7931(10) 0.4697(6) 0.3808(6) 0.049(2) Uani 1 1 d . . . H40 H 0.7253 0.4306 0.4299 0.058 Uiso 1 1 calc R . . O1W O 0.7381(6) 0.2389(4) 0.4326(4) 0.0521(15) Uani 1 1 d . . . O2W O 0.8745(6) 0.1987(4) -0.2885(4) 0.0561(15) Uani 1 1 d . . . O3W O 0.1299(11) 0.9551(8) 0.3820(7) 0.045(3) Uani 0.50 1 d PU . . O4W O 0.378(3) 0.0506(12) 0.1075(14) 0.151(8) Uani 0.50 1 d PU . . 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 0.0470(6) 0.0280(5) 0.0340(5) -0.0055(4) -0.0185(4) -0.0041(4) Zn2 0.0524(6) 0.0301(5) 0.0382(6) -0.0083(4) -0.0245(4) -0.0001(4) O1 0.046(3) 0.033(3) 0.040(3) -0.009(2) -0.027(3) -0.001(2) O3 0.049(3) 0.036(3) 0.071(4) -0.014(3) -0.027(3) -0.004(3) O4 0.065(4) 0.056(4) 0.051(4) -0.021(3) -0.035(3) -0.003(3) O5 0.067(4) 0.039(3) 0.055(4) -0.014(3) -0.019(3) -0.017(3) O6 0.077(4) 0.049(4) 0.061(4) -0.014(3) -0.048(3) -0.001(3) O7 0.143(7) 0.056(4) 0.121(6) -0.042(4) -0.101(5) 0.040(4) O11 0.044(3) 0.030(3) 0.026(3) -0.006(2) -0.017(2) 0.001(2) O13 0.061(4) 0.030(3) 0.053(4) -0.004(3) -0.027(3) -0.003(3) O14 0.064(4) 0.048(3) 0.034(3) -0.011(3) -0.019(3) -0.009(3) O15 0.077(4) 0.031(3) 0.063(4) -0.021(3) -0.033(3) 0.007(3) O16 0.072(4) 0.043(3) 0.039(3) -0.012(3) -0.035(3) 0.004(3) O17 0.073(4) 0.039(3) 0.047(4) 0.004(3) -0.029(3) -0.016(3) N1 0.043(4) 0.045(4) 0.052(5) -0.005(4) -0.013(3) -0.016(4) N2 0.043(4) 0.044(4) 0.034(4) -0.014(3) -0.017(3) -0.008(3) N3 0.042(4) 0.031(4) 0.036(4) -0.015(3) -0.017(3) 0.001(3) N4 0.042(4) 0.044(4) 0.058(5) -0.010(4) -0.015(3) -0.001(4) C1 0.038(4) 0.030(4) 0.027(4) -0.008(3) -0.012(3) -0.001(3) C2 0.046(5) 0.032(4) 0.047(5) -0.011(4) -0.022(4) -0.006(4) C3 0.057(5) 0.025(4) 0.035(5) -0.007(4) -0.015(4) -0.002(4) C4 0.035(4) 0.037(4) 0.028(4) -0.008(4) -0.014(3) -0.004(4) C5 0.031(4) 0.031(4) 0.024(4) -0.008(3) -0.009(3) -0.008(3) C10 0.042(5) 0.044(5) 0.045(5) -0.027(5) -0.014(4) 0.000(4) C11 0.034(4) 0.032(4) 0.025(4) -0.007(3) -0.014(3) 0.003(3) C12 0.042(4) 0.037(5) 0.031(4) -0.012(4) -0.016(3) 0.007(4) C13 0.036(4) 0.032(4) 0.032(4) -0.005(4) -0.007(3) -0.005(4) C14 0.045(4) 0.033(4) 0.032(4) -0.013(4) -0.012(3) -0.002(4) C15 0.038(4) 0.027(4) 0.027(4) -0.010(3) -0.011(3) -0.006(3) C51 0.063(5) 0.040(5) 0.023(4) 0.000(4) -0.015(4) -0.014(4) C110 0.042(5) 0.031(5) 0.036(5) -0.015(4) -0.009(4) 0.000(4) C151 0.044(5) 0.045(5) 0.031(5) -0.012(4) -0.003(4) -0.010(4) C21 0.055(6) 0.061(7) 0.081(8) -0.023(6) -0.005(5) -0.006(5) C22 0.058(7) 0.097(9) 0.078(8) -0.010(7) 0.004(6) -0.033(7) C23 0.068(7) 0.088(9) 0.078(8) -0.026(7) -0.013(6) -0.001(7) C24 0.063(6) 0.055(6) 0.069(7) -0.024(6) -0.024(5) 0.012(5) C25 0.052(5) 0.035(5) 0.049(5) -0.013(4) -0.030(4) 0.003(4) C26 0.047(5) 0.046(5) 0.038(5) -0.016(4) -0.021(4) -0.004(4) C27 0.064(6) 0.032(5) 0.076(7) -0.010(5) -0.040(5) 0.007(5) C28 0.082(7) 0.036(5) 0.070(7) 0.004(5) -0.046(6) -0.014(5) C29 0.062(6) 0.054(6) 0.049(6) -0.001(5) -0.023(5) -0.013(5) C30 0.051(5) 0.055(6) 0.054(6) -0.019(5) -0.017(5) -0.001(5) C31 0.055(6) 0.064(7) 0.079(7) -0.013(6) -0.010(6) 0.011(5) C32 0.046(6) 0.102(10) 0.090(9) -0.026(8) -0.002(6) 0.007(7) C33 0.077(8) 0.111(10) 0.061(7) -0.014(8) 0.010(6) -0.032(8) C34 0.072(7) 0.070(7) 0.060(7) -0.009(6) -0.010(5) -0.027(6) C35 0.047(5) 0.049(5) 0.046(5) -0.009(5) -0.015(4) -0.023(4) C36 0.050(5) 0.042(5) 0.037(5) 0.001(4) -0.022(4) -0.024(4) C37 0.072(6) 0.038(5) 0.065(6) 0.010(5) -0.036(5) -0.026(5) C38 0.078(7) 0.033(5) 0.087(8) -0.023(6) -0.050(6) 0.007(5) C39 0.073(6) 0.039(5) 0.069(7) -0.020(5) -0.029(5) 0.003(5) C40 0.057(5) 0.046(5) 0.045(5) -0.008(4) -0.019(4) -0.010(4) O1W 0.053(3) 0.053(4) 0.055(4) -0.019(3) -0.007(3) -0.018(3) O2W 0.062(4) 0.052(4) 0.045(3) -0.010(3) -0.017(3) 0.010(3) O3W 0.039(6) 0.038(6) 0.059(7) -0.022(6) -0.011(5) 0.004(5) O4W 0.25(2) 0.055(10) 0.154(17) 0.026(10) -0.099(16) -0.041(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O6 1.987(5) . ? Zn1 O14 2.011(5) . ? Zn1 O1W 2.089(5) . ? Zn1 N3 2.100(6) . ? Zn1 N4 2.122(7) . ? Zn2 O16 2.007(5) . ? Zn2 O4 2.023(5) 1_454 ? Zn2 N2 2.093(6) . ? Zn2 O2W 2.093(5) . ? Zn2 N1 2.118(6) . ? O1 C1 1.346(8) . ? O1 C5 1.363(7) . ? O3 C3 1.248(8) . ? O4 C10 1.246(9) . ? O4 Zn2 2.022(5) 1_656 ? O5 C10 1.239(9) . ? O6 C51 1.254(8) . ? O7 C51 1.201(9) . ? O11 C11 1.360(7) . ? O11 C15 1.375(7) . ? O13 C13 1.248(8) . ? O14 C110 1.252(8) . ? O15 C110 1.234(8) . ? O16 C151 1.259(8) . ? O17 C151 1.221(9) . ? N1 C21 1.304(10) . ? N1 C25 1.357(9) . ? N2 C30 1.334(10) . ? N2 C26 1.338(9) . ? N3 C40 1.330(9) . ? N3 C36 1.344(9) . ? N4 C31 1.332(10) . ? N4 C35 1.341(10) . ? C1 C2 1.338(9) . ? C1 C10 1.526(9) . ? C2 C3 1.451(9) . ? C3 C4 1.434(9) . ? C4 C5 1.312(9) . ? C5 C51 1.520(10) . ? C11 C12 1.332(9) . ? C11 C110 1.517(9) . ? C12 C13 1.444(9) . ? C13 C14 1.445(10) . ? C14 C15 1.330(9) . ? C15 C151 1.515(10) . ? C21 C22 1.386(12) . ? C22 C23 1.368(14) . ? C23 C24 1.354(13) . ? C24 C25 1.393(11) . ? C25 C26 1.473(11) . ? C26 C27 1.375(11) . ? C27 C28 1.352(12) . ? C28 C29 1.379(11) . ? C29 C30 1.376(11) . ? C31 C32 1.385(13) . ? C32 C33 1.349(14) . ? C33 C34 1.368(13) . ? C34 C35 1.388(11) . ? C35 C36 1.456(10) . ? C36 C37 1.403(11) . ? C37 C38 1.381(12) . ? C38 C39 1.360(12) . ? C39 C40 1.379(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Zn1 O14 97.3(2) . . ? O6 Zn1 O1W 99.7(2) . . ? O14 Zn1 O1W 86.4(2) . . ? O6 Zn1 N3 126.8(2) . . ? O14 Zn1 N3 135.0(2) . . ? O1W Zn1 N3 94.0(2) . . ? O6 Zn1 N4 95.5(2) . . ? O14 Zn1 N4 92.4(2) . . ? O1W Zn1 N4 164.8(2) . . ? N3 Zn1 N4 76.2(2) . . ? O16 Zn2 O4 100.7(2) . 1_454 ? O16 Zn2 N2 132.0(2) . . ? O4 Zn2 N2 126.4(2) 1_454 . ? O16 Zn2 O2W 87.5(2) . . ? O4 Zn2 O2W 97.9(2) 1_454 . ? N2 Zn2 O2W 94.2(2) . . ? O16 Zn2 N1 92.8(2) . . ? O4 Zn2 N1 93.5(2) 1_454 . ? N2 Zn2 N1 77.0(3) . . ? O2W Zn2 N1 168.4(2) . . ? C1 O1 C5 118.0(5) . . ? C10 O4 Zn2 111.6(5) . 1_656 ? C51 O6 Zn1 116.8(5) . . ? C11 O11 C15 118.2(5) . . ? C110 O14 Zn1 113.5(5) . . ? C151 O16 Zn2 111.3(5) . . ? C21 N1 C25 119.8(8) . . ? C21 N1 Zn2 124.9(6) . . ? C25 N1 Zn2 115.1(5) . . ? C30 N2 C26 118.9(7) . . ? C30 N2 Zn2 124.3(5) . . ? C26 N2 Zn2 116.8(5) . . ? C40 N3 C36 119.3(7) . . ? C40 N3 Zn1 124.5(5) . . ? C36 N3 Zn1 116.2(5) . . ? C31 N4 C35 119.2(8) . . ? C31 N4 Zn1 123.9(6) . . ? C35 N4 Zn1 116.5(5) . . ? C2 C1 O1 123.0(6) . . ? C2 C1 C10 124.3(6) . . ? O1 C1 C10 112.6(6) . . ? C1 C2 C3 120.6(7) . . ? O3 C3 C4 124.4(7) . . ? O3 C3 C2 122.1(7) . . ? C4 C3 C2 113.5(6) . . ? C5 C4 C3 121.9(6) . . ? C4 C5 O1 122.9(6) . . ? C4 C5 C51 126.1(6) . . ? O1 C5 C51 111.0(6) . . ? O5 C10 O4 126.8(7) . . ? O5 C10 C1 118.2(7) . . ? O4 C10 C1 115.0(7) . . ? C12 C11 O11 122.6(6) . . ? C12 C11 C110 124.1(6) . . ? O11 C11 C110 113.3(6) . . ? C11 C12 C13 121.9(7) . . ? O13 C13 C14 123.7(7) . . ? O13 C13 C12 123.2(7) . . ? C14 C13 C12 113.1(6) . . ? C15 C14 C13 122.2(6) . . ? C14 C15 O11 121.9(6) . . ? C14 C15 C151 126.2(6) . . ? O11 C15 C151 111.9(6) . . ? O7 C51 O6 126.4(8) . . ? O7 C51 C5 120.2(7) . . ? O6 C51 C5 113.3(7) . . ? O15 C110 O14 127.4(7) . . ? O15 C110 C11 118.7(7) . . ? O14 C110 C11 113.9(6) . . ? O17 C151 O16 127.2(7) . . ? O17 C151 C15 119.2(7) . . ? O16 C151 C15 113.5(7) . . ? N1 C21 C22 122.5(9) . . ? C23 C22 C21 118.1(10) . . ? C24 C23 C22 120.3(10) . . ? C23 C24 C25 119.1(9) . . ? N1 C25 C24 120.1(8) . . ? N1 C25 C26 115.2(7) . . ? C24 C25 C26 124.7(8) . . ? N2 C26 C27 121.0(8) . . ? N2 C26 C25 115.3(7) . . ? C27 C26 C25 123.6(8) . . ? C28 C27 C26 120.1(9) . . ? C27 C28 C29 119.4(8) . . ? C28 C29 C30 118.2(8) . . ? N2 C30 C29 122.4(8) . . ? N4 C31 C32 122.3(10) . . ? C33 C32 C31 118.1(10) . . ? C32 C33 C34 120.7(10) . . ? C33 C34 C35 118.8(10) . . ? N4 C35 C34 120.8(8) . . ? N4 C35 C36 114.3(7) . . ? C34 C35 C36 124.9(8) . . ? N3 C36 C37 118.9(8) . . ? N3 C36 C35 116.3(7) . . ? C37 C36 C35 124.8(8) . . ? C38 C37 C36 120.5(8) . . ? C39 C38 C37 119.7(8) . . ? C38 C39 C40 117.3(9) . . ? N3 C40 C39 124.3(8) . . ? _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.832 _refine_diff_density_max 0.667 _refine_diff_density_min -1.138 _refine_diff_density_rms 0.112 #===========================================================================END data_380_compound _database_code_depnum_ccdc_archive 'CCDC 779943' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 N2 O8 Zn' _chemical_formula_weight 463.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5318(14) _cell_length_b 10.7273(17) _cell_length_c 11.1772(18) _cell_angle_alpha 71.720(3) _cell_angle_beta 73.501(3) _cell_angle_gamma 70.674(2) _cell_volume 897.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7126 _exptl_absorpt_correction_T_max 1.0000 _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 5782 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.98 _reflns_number_total 4061 _reflns_number_gt 2841 _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^)+(0.0584P)^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 4061 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn -0.21587(5) 0.83773(4) 0.40693(4) 0.02910(15) Uani 1 1 d . . . O1 O -0.3831(3) 0.4526(2) 0.6096(2) 0.0284(5) Uani 1 1 d . . . O3 O -0.7472(4) 0.3569(3) 0.9214(3) 0.0520(8) Uani 1 1 d . . . O11 O -0.3415(3) 0.6962(2) 0.5175(2) 0.0368(6) Uani 1 1 d . . . O12 O -0.5297(4) 0.7712(2) 0.6834(3) 0.0465(7) Uani 1 1 d . . . O51 O -0.2940(3) 0.1095(2) 0.6054(3) 0.0429(7) Uani 1 1 d . . . O52 O -0.1649(3) 0.2721(2) 0.4887(3) 0.0416(7) Uani 1 1 d . . . O1W O -0.1504(4) 0.8716(3) 0.5502(3) 0.0365(6) Uani 1 1 d . . . O2W O -0.4202(4) 0.9677(3) 0.3431(3) 0.0407(7) Uani 1 1 d . . . N1 N -0.0544(4) 0.9545(3) 0.2595(3) 0.0303(7) Uani 1 1 d . . . N2 N -0.0515(4) 0.6921(3) 0.3083(3) 0.0290(7) Uani 1 1 d . . . C1 C -0.4897(4) 0.5481(3) 0.6726(3) 0.0257(7) Uani 1 1 d . . . C2 C -0.6139(5) 0.5218(3) 0.7722(3) 0.0298(8) Uani 1 1 d . . . H2 H -0.6863 0.5922 0.8092 0.036 Uiso 1 1 calc R . . C3 C -0.6395(5) 0.3861(3) 0.8246(3) 0.0322(8) Uani 1 1 d . . . C4 C -0.5241(5) 0.2902(3) 0.7531(3) 0.0313(8) Uani 1 1 d . . . H4 H -0.5334 0.2013 0.7780 0.038 Uiso 1 1 calc R . . C5 C -0.4030(4) 0.3242(3) 0.6514(3) 0.0265(7) Uani 1 1 d . . . C51 C -0.2766(4) 0.2284(3) 0.5739(3) 0.0283(8) Uani 1 1 d . . . C11 C -0.4496(4) 0.6863(3) 0.6194(3) 0.0282(8) Uani 1 1 d . . . C12 C -0.0569(5) 1.0847(4) 0.2378(4) 0.0409(10) Uani 1 1 d . . . H12 H -0.1366 1.1372 0.2914 0.049 Uiso 1 1 calc R . . C13 C 0.0565(6) 1.1448(4) 0.1371(4) 0.0483(11) Uani 1 1 d . . . H13 H 0.0515 1.2358 0.1247 0.058 Uiso 1 1 calc R . . C14 C 0.1745(5) 1.0697(4) 0.0571(4) 0.0456(10) Uani 1 1 d . . . H14 H 0.2498 1.1096 -0.0100 0.055 Uiso 1 1 calc R . . C15 C 0.1818(5) 0.9321(4) 0.0763(3) 0.0372(9) Uani 1 1 d . . . C16 C 0.0622(4) 0.8799(3) 0.1803(3) 0.0298(8) Uani 1 1 d . . . C17 C 0.0650(4) 0.7386(3) 0.2061(3) 0.0291(8) Uani 1 1 d . . . C18 C 0.1820(5) 0.6570(4) 0.1280(4) 0.0352(8) Uani 1 1 d . . . C19 C 0.3014(5) 0.7135(4) 0.0230(4) 0.0438(10) Uani 1 1 d . . . H19 H 0.3808 0.6587 -0.0286 0.053 Uiso 1 1 calc R . . C20 C 0.2992(5) 0.8456(4) -0.0012(4) 0.0464(10) Uani 1 1 d . . . H20 H 0.3765 0.8805 -0.0704 0.056 Uiso 1 1 calc R . . C21 C 0.1787(5) 0.5188(4) 0.1592(4) 0.0421(9) Uani 1 1 d . . . H21 H 0.2541 0.4602 0.1096 0.051 Uiso 1 1 calc R . . C22 C 0.0644(5) 0.4732(4) 0.2621(4) 0.0437(10) Uani 1 1 d . . . H22 H 0.0618 0.3828 0.2836 0.052 Uiso 1 1 calc R . . C23 C -0.0489(5) 0.5614(3) 0.3357(4) 0.0344(8) Uani 1 1 d . . . H23 H -0.1255 0.5279 0.4064 0.041 Uiso 1 1 calc R . . H2WA H -0.445(7) 1.030(5) 0.344(5) 0.065(19) Uiso 1 1 d . . . H1WA H -0.048(6) 0.841(5) 0.547(4) 0.061(16) Uiso 1 1 d . . . H1WB H -0.190(6) 0.946(5) 0.563(4) 0.062(15) Uiso 1 1 d . . . H2WB H -0.517(8) 0.943(6) 0.366(5) 0.10(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 Zn 0.0306(2) 0.0226(2) 0.0348(3) -0.00820(16) 0.00195(17) -0.01406(17) O1 0.0307(14) 0.0190(10) 0.0355(13) -0.0082(10) 0.0013(11) -0.0119(10) O3 0.060(2) 0.0439(15) 0.0491(18) -0.0146(14) 0.0208(15) -0.0339(16) O11 0.0445(16) 0.0269(12) 0.0396(15) -0.0075(11) 0.0043(12) -0.0215(12) O12 0.0519(18) 0.0239(12) 0.0588(18) -0.0185(12) 0.0145(14) -0.0174(12) O51 0.0322(15) 0.0263(12) 0.076(2) -0.0258(13) -0.0019(14) -0.0102(11) O52 0.0373(16) 0.0328(13) 0.0492(17) -0.0129(12) 0.0076(13) -0.0134(12) O1W 0.0325(17) 0.0307(14) 0.0520(18) -0.0210(13) -0.0033(13) -0.0096(13) O2W 0.0299(16) 0.0188(13) 0.073(2) -0.0088(13) -0.0069(14) -0.0109(12) N1 0.0284(16) 0.0268(14) 0.0359(17) -0.0050(12) -0.0019(13) -0.0139(13) N2 0.0294(16) 0.0271(14) 0.0318(16) -0.0062(12) 0.0005(13) -0.0156(13) C1 0.0252(18) 0.0223(15) 0.0308(18) -0.0074(14) -0.0024(14) -0.0094(14) C2 0.032(2) 0.0216(15) 0.037(2) -0.0117(14) -0.0016(16) -0.0083(15) C3 0.036(2) 0.0309(17) 0.032(2) -0.0092(15) 0.0022(16) -0.0179(16) C4 0.037(2) 0.0206(15) 0.041(2) -0.0065(14) -0.0040(16) -0.0174(15) C5 0.0292(19) 0.0196(14) 0.0360(19) -0.0068(14) -0.0065(15) -0.0132(14) C51 0.0256(19) 0.0248(16) 0.040(2) -0.0127(15) -0.0080(16) -0.0079(15) C11 0.0301(19) 0.0212(15) 0.035(2) -0.0059(14) -0.0052(16) -0.0111(15) C12 0.042(2) 0.0315(18) 0.053(3) -0.0074(18) -0.0071(19) -0.0197(18) C13 0.052(3) 0.0340(19) 0.060(3) 0.0036(19) -0.013(2) -0.025(2) C14 0.046(3) 0.049(2) 0.042(2) 0.0040(19) -0.003(2) -0.031(2) C15 0.036(2) 0.048(2) 0.030(2) -0.0033(17) -0.0020(16) -0.0234(19) C16 0.0274(19) 0.0334(17) 0.0303(19) -0.0033(15) -0.0067(15) -0.0139(16) C17 0.0292(19) 0.0317(17) 0.0287(18) -0.0054(14) -0.0068(15) -0.0120(15) C18 0.037(2) 0.040(2) 0.031(2) -0.0124(16) -0.0062(16) -0.0102(18) C19 0.038(2) 0.061(3) 0.033(2) -0.0196(19) 0.0045(18) -0.017(2) C20 0.038(2) 0.069(3) 0.030(2) -0.008(2) 0.0046(18) -0.027(2) C21 0.041(2) 0.040(2) 0.047(2) -0.0232(18) -0.0051(19) -0.0045(19) C22 0.050(3) 0.0300(18) 0.053(3) -0.0110(18) -0.010(2) -0.0133(19) C23 0.038(2) 0.0277(16) 0.037(2) -0.0069(15) -0.0027(17) -0.0136(16) _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 Zn O2W 1.992(3) . ? Zn O1W 2.004(3) . ? Zn O11 2.032(2) . ? Zn N2 2.092(3) . ? Zn N1 2.177(3) . ? O1 C1 1.358(4) . ? O1 C5 1.361(3) . ? O3 C3 1.235(4) . ? O11 C11 1.246(4) . ? O12 C11 1.236(4) . ? O51 C51 1.260(4) . ? O52 C51 1.239(4) . ? N1 C12 1.335(4) . ? N1 C16 1.353(5) . ? N2 C23 1.331(4) . ? N2 C17 1.367(4) . ? C1 C2 1.331(5) . ? C1 C11 1.528(4) . ? C2 C3 1.454(4) . ? C3 C4 1.437(5) . ? C4 C5 1.347(5) . ? C5 C51 1.505(5) . ? C12 C13 1.399(5) . ? C13 C14 1.366(6) . ? C14 C15 1.406(5) . ? C15 C16 1.415(5) . ? C15 C20 1.419(5) . ? C16 C17 1.444(4) . ? C17 C18 1.390(5) . ? C18 C21 1.420(5) . ? C18 C19 1.438(5) . ? C19 C20 1.351(5) . ? C21 C22 1.356(6) . ? C22 C23 1.392(5) . ? 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 O2W Zn O1W 117.60(13) . . ? O2W Zn O11 93.73(11) . . ? O1W Zn O11 96.96(11) . . ? O2W Zn N2 121.22(13) . . ? O1W Zn N2 120.34(12) . . ? O11 Zn N2 88.59(10) . . ? O2W Zn N1 90.39(12) . . ? O1W Zn N1 92.79(11) . . ? O11 Zn N1 166.17(10) . . ? N2 Zn N1 78.00(10) . . ? C1 O1 C5 118.4(3) . . ? C11 O11 Zn 135.5(2) . . ? C12 N1 C16 118.1(3) . . ? C12 N1 Zn 129.4(3) . . ? C16 N1 Zn 112.5(2) . . ? C23 N2 C17 118.0(3) . . ? C23 N2 Zn 126.9(2) . . ? C17 N2 Zn 115.1(2) . . ? C2 C1 O1 122.9(3) . . ? C2 C1 C11 123.9(3) . . ? O1 C1 C11 113.2(3) . . ? C1 C2 C3 121.8(3) . . ? O3 C3 C4 124.1(3) . . ? O3 C3 C2 123.2(3) . . ? C4 C3 C2 112.6(3) . . ? C5 C4 C3 122.5(3) . . ? C4 C5 O1 121.7(3) . . ? C4 C5 C51 125.2(3) . . ? O1 C5 C51 113.1(3) . . ? O52 C51 O51 126.7(3) . . ? O52 C51 C5 117.7(3) . . ? O51 C51 C5 115.6(3) . . ? O12 C11 O11 129.9(3) . . ? O12 C11 C1 115.3(3) . . ? O11 C11 C1 114.8(3) . . ? N1 C12 C13 122.1(4) . . ? C14 C13 C12 120.0(4) . . ? C13 C14 C15 119.9(4) . . ? C14 C15 C16 116.3(4) . . ? C14 C15 C20 124.3(4) . . ? C16 C15 C20 119.4(3) . . ? N1 C16 C15 123.6(3) . . ? N1 C16 C17 117.4(3) . . ? C15 C16 C17 118.9(3) . . ? N2 C17 C18 123.0(3) . . ? N2 C17 C16 117.0(3) . . ? C18 C17 C16 120.0(3) . . ? C17 C18 C21 117.1(3) . . ? C17 C18 C19 119.6(3) . . ? C21 C18 C19 123.3(4) . . ? C20 C19 C18 120.6(4) . . ? C19 C20 C15 121.5(4) . . ? C22 C21 C18 119.3(4) . . ? C21 C22 C23 120.2(3) . . ? N2 C23 C22 122.3(3) . . ? 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 O2W H2WA O12 0.63(5) 2.01(5) 2.621(4) 166(7) 2_476 O1W H1WA O52 0.82(5) 1.83(5) 2.610(4) 157(5) 2_566 O1W H1WB O51 0.80(5) 1.83(5) 2.624(4) 175(5) 1_565 O2W H2WB O51 0.90(6) 1.79(6) 2.684(4) 174(5) 2_466 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.807 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.092 #===========================================================================END data_388_compound _database_code_depnum_ccdc_archive 'CCDC 779944' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O10 Zn' _chemical_formula_weight 499.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6821(8) _cell_length_b 9.8561(10) _cell_length_c 13.5031(14) _cell_angle_alpha 84.562(2) _cell_angle_beta 80.973(2) _cell_angle_gamma 76.465(2) _cell_volume 979.89(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8484 _exptl_absorpt_correction_T_max 1.0000 _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 6306 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.03 _reflns_number_total 4435 _reflns_number_gt 3428 _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^)+(0.0746P)^2^+0.2376P] 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 4435 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Zn Zn 0.58294(5) 0.70260(4) 0.77368(3) 0.02458(14) Uani 1 1 d . . . N1 N 0.6896(4) 0.5805(3) 0.6412(2) 0.0327(7) Uani 1 1 d . . . N2 N 0.4347(4) 0.8208(3) 0.6594(2) 0.0313(7) Uani 1 1 d . . . O1W O 0.4565(4) 0.8328(3) 0.8837(2) 0.0353(6) Uani 1 1 d . . . O2W O 0.3985(4) 0.5784(3) 0.8239(2) 0.0377(7) Uani 1 1 d . . . O3W O 0.7921(5) 0.8278(4) 0.7288(3) 0.0464(8) Uani 1 1 d . . . O11 O 0.7580(3) 0.5693(3) 0.85745(19) 0.0323(6) Uani 1 1 d . . . O1 O 1.1874(3) 0.3609(2) 0.87922(18) 0.0255(5) Uani 1 1 d . . . O3 O 0.9108(4) 0.1255(3) 1.0787(2) 0.0365(6) Uani 1 1 d . . . O12 O 1.0348(3) 0.6008(3) 0.7956(2) 0.0348(6) Uani 1 1 d . . . O13 O 1.5501(3) 0.0764(3) 0.8825(2) 0.0391(7) Uani 1 1 d . . . O14 O 1.5475(3) 0.3026(3) 0.8509(2) 0.0373(6) Uani 1 1 d . . . C1 C 1.0042(5) 0.4004(3) 0.9028(3) 0.0250(7) Uani 1 1 d . . . C2 C 0.9076(5) 0.3256(4) 0.9664(3) 0.0264(7) Uani 1 1 d . . . H2 H 0.7828 0.3569 0.9795 0.032 Uiso 1 1 calc R . . C3 C 0.9943(5) 0.1959(4) 1.0157(3) 0.0260(7) Uani 1 1 d . . . C4 C 1.1873(5) 0.1551(3) 0.9851(3) 0.0258(7) Uani 1 1 d . . . H4 H 1.2522 0.0711 1.0112 0.031 Uiso 1 1 calc R . . C5 C 1.2744(4) 0.2364(3) 0.9195(2) 0.0232(7) Uani 1 1 d . . . C11 C 0.9275(5) 0.5370(3) 0.8464(3) 0.0246(7) Uani 1 1 d . . . C51 C 1.4749(5) 0.2035(4) 0.8818(3) 0.0265(7) Uani 1 1 d . . . C12 C 0.8008(6) 0.4556(4) 0.6339(4) 0.0441(10) Uani 1 1 d . . . H12 H 0.8431 0.4092 0.6917 0.053 Uiso 1 1 calc R . . C13 C 0.8572(6) 0.3905(5) 0.5430(4) 0.0530(12) Uani 1 1 d . . . H13 H 0.9351 0.3027 0.5413 0.064 Uiso 1 1 calc R . . C14 C 0.7977(6) 0.4561(5) 0.4568(4) 0.0503(12) Uani 1 1 d . . . H14 H 0.8365 0.4143 0.3959 0.060 Uiso 1 1 calc R . . C15 C 0.6778(6) 0.5871(5) 0.4612(3) 0.0426(10) Uani 1 1 d . . . C16 C 0.6246(5) 0.6445(4) 0.5555(3) 0.0330(8) Uani 1 1 d . . . C17 C 0.4889(5) 0.7730(4) 0.5658(3) 0.0298(8) Uani 1 1 d . . . C18 C 0.4136(6) 0.8398(5) 0.4811(3) 0.0409(10) Uani 1 1 d . . . C19 C 0.2741(6) 0.9609(5) 0.4962(3) 0.0499(12) Uani 1 1 d . . . H19 H 0.2217 1.0096 0.4419 0.060 Uiso 1 1 calc R . . C20 C 0.2169(6) 1.0058(5) 0.5901(4) 0.0513(12) Uani 1 1 d . . . H20 H 0.1226 1.0838 0.6011 0.062 Uiso 1 1 calc R . . C21 C 0.3015(6) 0.9330(4) 0.6708(3) 0.0404(9) Uani 1 1 d . . . H21 H 0.2621 0.9653 0.7348 0.048 Uiso 1 1 calc R . . C22 C 0.4750(7) 0.7827(6) 0.3855(3) 0.0542(13) Uani 1 1 d . . . H22 H 0.4281 0.8291 0.3290 0.065 Uiso 1 1 calc R . . C23 C 0.6008(7) 0.6616(6) 0.3762(3) 0.0537(13) Uani 1 1 d . . . H23 H 0.6384 0.6257 0.3132 0.064 Uiso 1 1 calc R . . O4W O 0.0911(6) 0.9124(7) 0.2188(3) 0.117(2) Uani 1 1 d . . . H2WA H 0.295(6) 0.583(4) 0.815(3) 0.029(11) Uiso 1 1 d . . . H2WB H 0.435(5) 0.491(4) 0.845(3) 0.030(10) Uiso 1 1 d . . . H1WA H 0.355(6) 0.845(5) 0.899(3) 0.034(13) Uiso 1 1 d . . . H1WB H 0.478(7) 0.912(6) 0.892(4) 0.067(17) Uiso 1 1 d . . . H3WA H 0.822(11) 0.889(8) 0.726(6) 0.11(3) Uiso 1 1 d . . . H3WB H 0.870(17) 0.753(14) 0.777(10) 0.26(6) 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 Zn 0.0253(2) 0.0220(2) 0.0255(2) 0.00005(15) -0.00557(16) -0.00268(15) N1 0.0360(18) 0.0300(16) 0.0339(17) -0.0052(13) -0.0057(14) -0.0092(14) N2 0.0365(17) 0.0313(16) 0.0261(16) -0.0007(12) -0.0074(13) -0.0062(14) O1W 0.0309(16) 0.0339(15) 0.0421(17) -0.0123(12) -0.0023(13) -0.0071(13) O2W 0.0239(14) 0.0263(14) 0.0623(19) 0.0069(13) -0.0070(13) -0.0074(11) O3W 0.0459(18) 0.0427(18) 0.058(2) 0.0207(15) -0.0226(15) -0.0226(15) O11 0.0247(13) 0.0320(13) 0.0371(15) 0.0079(11) -0.0077(11) -0.0017(10) O1 0.0188(11) 0.0235(12) 0.0319(13) 0.0060(10) -0.0029(10) -0.0038(9) O3 0.0300(14) 0.0313(14) 0.0431(16) 0.0093(12) 0.0067(12) -0.0092(11) O12 0.0282(14) 0.0330(14) 0.0425(16) 0.0122(12) -0.0097(12) -0.0082(11) O13 0.0213(13) 0.0301(14) 0.0603(18) 0.0077(13) -0.0014(12) -0.0019(11) O14 0.0274(14) 0.0323(14) 0.0515(17) 0.0090(12) -0.0046(12) -0.0105(11) C1 0.0237(17) 0.0225(16) 0.0287(18) -0.0022(13) -0.0067(14) -0.0027(13) C2 0.0211(16) 0.0280(17) 0.0290(18) -0.0004(14) -0.0034(14) -0.0039(14) C3 0.0264(17) 0.0243(17) 0.0270(18) -0.0013(13) -0.0047(14) -0.0044(14) C4 0.0223(16) 0.0229(16) 0.0312(19) 0.0028(13) -0.0042(14) -0.0047(13) C5 0.0216(16) 0.0208(15) 0.0270(17) 0.0014(13) -0.0068(13) -0.0033(13) C11 0.0258(17) 0.0222(16) 0.0257(17) 0.0004(13) -0.0090(14) -0.0024(14) C51 0.0225(17) 0.0300(18) 0.0266(18) 0.0045(14) -0.0067(14) -0.0056(14) C12 0.041(2) 0.034(2) 0.057(3) -0.0089(19) -0.009(2) -0.0054(18) C13 0.041(2) 0.041(2) 0.077(4) -0.028(2) 0.009(2) -0.010(2) C14 0.050(3) 0.059(3) 0.047(3) -0.025(2) 0.012(2) -0.028(2) C15 0.045(2) 0.060(3) 0.032(2) -0.0135(19) 0.0054(18) -0.032(2) C16 0.034(2) 0.040(2) 0.031(2) -0.0075(16) 0.0003(16) -0.0203(17) C17 0.0296(19) 0.037(2) 0.0268(18) 0.0021(15) -0.0060(15) -0.0159(16) C18 0.046(2) 0.054(3) 0.031(2) 0.0088(18) -0.0135(18) -0.027(2) C19 0.049(3) 0.061(3) 0.041(2) 0.022(2) -0.022(2) -0.016(2) C20 0.044(3) 0.052(3) 0.051(3) 0.013(2) -0.016(2) 0.002(2) C21 0.041(2) 0.039(2) 0.036(2) 0.0044(17) -0.0097(18) 0.0017(18) C22 0.066(3) 0.081(4) 0.028(2) 0.005(2) -0.012(2) -0.041(3) C23 0.065(3) 0.080(4) 0.028(2) -0.010(2) 0.003(2) -0.044(3) O4W 0.054(2) 0.209(6) 0.051(2) -0.020(3) 0.001(2) 0.041(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 Zn O1W 2.030(3) . ? Zn O11 2.045(2) . ? Zn O2W 2.079(3) . ? Zn N2 2.151(3) . ? Zn N1 2.192(3) . ? Zn O3W 2.225(3) . ? N1 C12 1.327(5) . ? N1 C16 1.372(5) . ? N2 C21 1.322(5) . ? N2 C17 1.360(5) . ? O11 C11 1.255(4) . ? O1 C5 1.360(4) . ? O1 C1 1.364(4) . ? O3 C3 1.242(4) . ? O12 C11 1.236(4) . ? O13 C51 1.250(4) . ? O14 C51 1.242(4) . ? C1 C2 1.330(5) . ? C1 C11 1.522(4) . ? C2 C3 1.448(5) . ? C3 C4 1.446(5) . ? C4 C5 1.344(5) . ? C5 C51 1.513(5) . ? C12 C13 1.399(6) . ? C13 C14 1.367(7) . ? C14 C15 1.400(7) . ? C15 C16 1.404(5) . ? C15 C23 1.434(6) . ? C16 C17 1.442(5) . ? C17 C18 1.401(5) . ? C18 C19 1.412(7) . ? C18 C22 1.424(6) . ? C19 C20 1.356(7) . ? C20 C21 1.407(5) . ? C22 C23 1.351(7) . ? 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 O1W Zn O11 97.13(11) . . ? O1W Zn O2W 88.07(13) . . ? O11 Zn O2W 87.34(11) . . ? O1W Zn N2 94.62(12) . . ? O11 Zn N2 167.96(11) . . ? O2W Zn N2 95.70(12) . . ? O1W Zn N1 171.44(12) . . ? O11 Zn N1 91.40(11) . . ? O2W Zn N1 91.53(12) . . ? N2 Zn N1 76.90(12) . . ? O1W Zn O3W 91.40(14) . . ? O11 Zn O3W 88.59(11) . . ? O2W Zn O3W 175.79(11) . . ? N2 Zn O3W 88.51(11) . . ? N1 Zn O3W 89.62(13) . . ? C12 N1 C16 117.4(4) . . ? C12 N1 Zn 129.5(3) . . ? C16 N1 Zn 113.1(2) . . ? C21 N2 C17 118.1(3) . . ? C21 N2 Zn 127.2(3) . . ? C17 N2 Zn 114.7(2) . . ? C11 O11 Zn 131.0(2) . . ? C5 O1 C1 118.4(3) . . ? C2 C1 O1 123.0(3) . . ? C2 C1 C11 125.4(3) . . ? O1 C1 C11 111.6(3) . . ? C1 C2 C3 120.9(3) . . ? O3 C3 C4 122.6(3) . . ? O3 C3 C2 123.2(3) . . ? C4 C3 C2 114.2(3) . . ? C5 C4 C3 121.1(3) . . ? C4 C5 O1 122.3(3) . . ? C4 C5 C51 125.5(3) . . ? O1 C5 C51 112.2(3) . . ? O12 C11 O11 128.1(3) . . ? O12 C11 C1 118.2(3) . . ? O11 C11 C1 113.6(3) . . ? O14 C51 O13 126.4(3) . . ? O14 C51 C5 118.1(3) . . ? O13 C51 C5 115.5(3) . . ? N1 C12 C13 122.8(4) . . ? C14 C13 C12 119.9(4) . . ? C13 C14 C15 119.2(4) . . ? C14 C15 C16 117.5(4) . . ? C14 C15 C23 123.6(4) . . ? C16 C15 C23 118.8(4) . . ? N1 C16 C15 123.0(4) . . ? N1 C16 C17 117.2(3) . . ? C15 C16 C17 119.7(4) . . ? N2 C17 C18 122.9(4) . . ? N2 C17 C16 117.7(3) . . ? C18 C17 C16 119.4(4) . . ? C17 C18 C19 117.2(4) . . ? C17 C18 C22 119.9(4) . . ? C19 C18 C22 122.9(4) . . ? C20 C19 C18 119.7(4) . . ? C19 C20 C21 119.3(4) . . ? N2 C21 C20 122.8(4) . . ? C23 C22 C18 120.6(4) . . ? C22 C23 C15 121.5(4) . . ? 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 O2W H2WA O12 0.81(4) 2.02(4) 2.834(4) 178(4) 1_455 O2W H2WA O1 0.81(4) 2.55(4) 2.954(3) 112(3) 1_455 O2W H2WB O14 0.87(4) 1.86(4) 2.705(4) 163(4) 1_455 O2W H2WA O1 0.81(4) 2.55(4) 2.954(3) 112(3) 1_455 O1W H1WA O3 0.76(5) 1.97(5) 2.727(4) 174(5) 2_667 O1W H1WB O13 0.85(6) 1.82(6) 2.661(4) 168(5) 1_465 O3W H3WA O4W 0.69(7) 2.42(7) 3.080(8) 160(8) 2_676 O3W H3WB O12 1.07(14) 1.75(13) 2.736(4) 151(10) . O3W H3WB O11 1.07(14) 2.30(13) 2.985(4) 120(9) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.641 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.151 #============================================ data_5 _database_code_depnum_ccdc_archive 'CCDC 779945' #TrackingRef '- Mat_dep.cif' ################ # CCDC 779945 # ################ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 N2 Ni O11' _chemical_formula_weight 511.08 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.9267(15) _cell_length_b 23.869(4) _cell_length_c 8.9977(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.911(3) _cell_angle_gamma 90.00 _cell_volume 2145.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1680 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 23.31 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796945 _exptl_absorpt_correction_T_max 1.000000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3627 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_sigmaI/netI 0.1024 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3627 _reflns_number_gt 2018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.058(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3627 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1420 _refine_ls_R_factor_gt 0.0829 _refine_ls_wR_factor_ref 0.2581 _refine_ls_wR_factor_gt 0.2139 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Ni1 Ni 0.20228(10) 0.10801(4) 0.28135(13) 0.0443(5) Uani 1 1 d . . . O1 O 0.6066(5) 0.0641(2) 0.1078(7) 0.0451(13) Uani 1 1 d . . . N1 N 0.1640(6) 0.1928(2) 0.2576(8) 0.0422(16) Uani 1 1 d . . . C1 C 0.5217(8) 0.1031(3) 0.1199(9) 0.0421(18) Uani 1 1 d . . . N2 N 0.0362(7) 0.1114(2) 0.3417(9) 0.0499(17) Uani 1 1 d . . . C2 C 0.5075(8) 0.1535(3) 0.0512(10) 0.047(2) Uani 1 1 d . . . H2 H 0.4501 0.1795 0.0661 0.056 Uiso 1 1 calc R . . O3 O 0.5667(6) 0.2148(2) -0.1170(8) 0.0646(18) Uani 1 1 d . . . C3 C 0.5805(8) 0.1682(3) -0.0463(10) 0.046(2) Uani 1 1 d . . . C4 C 0.6691(9) 0.1258(3) -0.0530(11) 0.054(2) Uani 1 1 d . . . H4 H 0.7227 0.1330 -0.1089 0.064 Uiso 1 1 calc R . . C5 C 0.6784(8) 0.0765(3) 0.0171(10) 0.0441(19) Uani 1 1 d . . . C10 C 0.4447(8) 0.0846(3) 0.2178(10) 0.046(2) Uani 1 1 d . . . O11 O 0.3543(6) 0.1178(2) 0.2090(7) 0.0546(15) Uani 1 1 d . . . C11 C 0.2327(9) 0.2335(3) 0.2265(10) 0.052(2) Uani 1 1 d . . . H11 H 0.3021 0.2237 0.1968 0.063 Uiso 1 1 calc R . . O12 O 0.4764(6) 0.0396(2) 0.2951(8) 0.0670(19) Uani 1 1 d . . . C12 C 0.2072(9) 0.2900(3) 0.2359(11) 0.057(2) Uani 1 1 d . . . H12 H 0.2575 0.3171 0.2116 0.068 Uiso 1 1 calc R . . C13 C 0.1081(10) 0.3050(4) 0.2808(11) 0.064(3) Uani 1 1 d . . . H13 H 0.0913 0.3427 0.2910 0.077 Uiso 1 1 calc R . . C14 C 0.0312(9) 0.2639(3) 0.3118(11) 0.053(2) Uani 1 1 d . . . C15 C 0.0648(8) 0.2082(3) 0.3031(10) 0.0466(19) Uani 1 1 d . . . C16 C -0.0765(10) 0.2765(4) 0.3615(12) 0.065(3) Uani 1 1 d . . . H16 H -0.0982 0.3136 0.3710 0.078 Uiso 1 1 calc R . . C17 C -0.1449(9) 0.2352(4) 0.3940(12) 0.065(3) Uani 1 1 d . . . H17 H -0.2172 0.2442 0.4190 0.078 Uiso 1 1 calc R . . C18 C -0.1094(8) 0.1774(4) 0.3910(10) 0.052(2) Uani 1 1 d . . . C19 C -0.1710(9) 0.1330(4) 0.4349(11) 0.061(2) Uani 1 1 d . . . H19 H -0.2406 0.1400 0.4666 0.073 Uiso 1 1 calc R . . C20 C -0.1301(9) 0.0805(4) 0.4315(12) 0.064(3) Uani 1 1 d . . . H20 H -0.1706 0.0508 0.4609 0.077 Uiso 1 1 calc R . . C21 C -0.0256(9) 0.0709(4) 0.3831(11) 0.059(2) Uani 1 1 d . . . H21 H 0.0016 0.0342 0.3800 0.071 Uiso 1 1 calc R . . C22 C -0.0060(8) 0.1641(3) 0.3433(10) 0.0470(19) Uani 1 1 d . . . O51 O 0.8403(6) 0.0419(2) -0.0637(8) 0.0616(17) Uani 1 1 d . . . C51 C 0.7690(8) 0.0299(4) 0.0128(10) 0.052(2) Uani 1 1 d . . . O52 O 0.7677(6) -0.0163(2) 0.0783(8) 0.0662(18) Uani 1 1 d . . . O1W O 0.2366(6) 0.0226(2) 0.3319(7) 0.0542(15) Uani 1 1 d . . . O2W O 0.0854(6) 0.0900(2) 0.0364(7) 0.0550(15) Uani 1 1 d . . . O3W O 0.3292(6) 0.1243(2) 0.5183(7) 0.0541(15) Uani 1 1 d . . . O5W O 0.5573(7) 0.1901(3) 0.5662(9) 0.083(2) Uani 1 1 d . . . O6W O 0.3766(7) 0.0484(2) 0.7450(8) 0.0718(19) 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 Ni1 0.0450(7) 0.0382(6) 0.0624(8) 0.0016(5) 0.0349(6) 0.0017(5) O1 0.042(3) 0.044(3) 0.061(3) 0.001(2) 0.033(3) 0.002(2) N1 0.041(4) 0.041(3) 0.053(4) 0.000(3) 0.028(3) 0.002(3) C1 0.039(5) 0.044(4) 0.050(5) -0.007(4) 0.025(4) 0.000(3) N2 0.052(4) 0.039(4) 0.067(5) 0.000(3) 0.032(4) 0.001(3) C2 0.048(5) 0.039(4) 0.067(6) -0.001(4) 0.037(5) 0.003(4) O3 0.075(5) 0.051(3) 0.088(5) 0.010(3) 0.054(4) 0.003(3) C3 0.045(5) 0.046(4) 0.059(5) -0.003(4) 0.033(4) -0.010(4) C4 0.055(6) 0.052(5) 0.071(6) -0.013(4) 0.044(5) -0.005(4) C5 0.039(5) 0.052(5) 0.053(5) -0.008(4) 0.031(4) -0.005(4) C10 0.042(5) 0.048(4) 0.061(5) 0.005(4) 0.032(4) 0.007(4) O11 0.056(4) 0.045(3) 0.081(4) 0.002(3) 0.046(3) 0.004(3) C11 0.057(6) 0.048(5) 0.064(6) 0.003(4) 0.038(5) -0.003(4) O12 0.068(4) 0.061(4) 0.096(5) 0.026(3) 0.059(4) 0.017(3) C12 0.069(7) 0.040(5) 0.065(6) 0.002(4) 0.030(5) -0.006(4) C13 0.075(7) 0.045(5) 0.067(6) 0.002(4) 0.022(5) 0.006(5) C14 0.053(6) 0.051(5) 0.060(5) 0.001(4) 0.027(5) 0.006(4) C15 0.042(5) 0.047(5) 0.049(5) -0.005(4) 0.017(4) -0.001(4) C16 0.067(7) 0.061(6) 0.079(7) 0.002(5) 0.043(6) 0.027(5) C17 0.054(6) 0.078(6) 0.075(6) -0.007(5) 0.039(5) 0.016(5) C18 0.041(5) 0.067(5) 0.055(5) -0.013(4) 0.026(4) -0.003(4) C19 0.044(6) 0.089(7) 0.059(6) -0.001(5) 0.030(5) 0.000(5) C20 0.056(6) 0.079(7) 0.077(7) -0.001(5) 0.046(6) -0.009(5) C21 0.060(6) 0.055(5) 0.072(6) 0.005(5) 0.039(5) -0.007(4) C22 0.039(5) 0.058(5) 0.044(5) -0.007(4) 0.018(4) -0.001(4) O51 0.058(4) 0.063(4) 0.085(5) -0.017(3) 0.051(4) -0.006(3) C51 0.045(5) 0.057(5) 0.058(5) -0.017(4) 0.026(4) -0.001(4) O52 0.069(4) 0.052(4) 0.098(5) 0.001(3) 0.055(4) 0.013(3) O1W 0.070(4) 0.042(3) 0.068(4) 0.004(3) 0.045(3) 0.002(3) O2W 0.060(4) 0.044(3) 0.075(4) 0.004(3) 0.042(3) -0.001(3) O3W 0.054(4) 0.053(3) 0.064(4) 0.002(3) 0.034(3) 0.000(3) O5W 0.087(5) 0.079(4) 0.080(5) -0.002(4) 0.031(4) -0.023(4) O6W 0.090(5) 0.056(4) 0.080(5) 0.014(3) 0.045(4) 0.010(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 Ni1 O11 2.028(5) . ? Ni1 O3W 2.055(6) . ? Ni1 N1 2.059(6) . ? Ni1 O1W 2.090(5) . ? Ni1 N2 2.096(6) . ? Ni1 O2W 2.096(6) . ? O1 C1 1.350(8) . ? O1 C5 1.373(8) . ? N1 C11 1.327(9) . ? N1 C15 1.355(9) . ? C1 C2 1.332(10) . ? C1 C10 1.510(10) . ? N2 C21 1.316(9) . ? N2 C22 1.342(9) . ? C2 C3 1.448(10) . ? O3 C3 1.259(9) . ? C3 C4 1.419(10) . ? C4 C5 1.320(10) . ? C5 C51 1.500(10) . ? C10 O11 1.244(9) . ? C10 O12 1.249(9) . ? C11 C12 1.386(11) . ? C12 C13 1.348(12) . ? C13 C14 1.393(11) . ? C14 C15 1.390(10) . ? C14 C16 1.450(11) . ? C15 C22 1.437(10) . ? C16 C17 1.339(12) . ? C17 C18 1.437(11) . ? C18 C19 1.395(12) . ? C18 C22 1.398(10) . ? C19 C20 1.335(12) . ? C20 C21 1.396(11) . ? O51 C51 1.264(9) . ? C51 O52 1.254(10) . ? 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 O11 Ni1 O3W 90.9(2) . . ? O11 Ni1 N1 90.7(2) . . ? O3W Ni1 N1 86.9(2) . . ? O11 Ni1 O1W 94.83(19) . . ? O3W Ni1 O1W 88.4(2) . . ? N1 Ni1 O1W 172.8(2) . . ? O11 Ni1 N2 170.5(2) . . ? O3W Ni1 N2 90.8(2) . . ? N1 Ni1 N2 80.1(2) . . ? O1W Ni1 N2 94.5(2) . . ? O11 Ni1 O2W 85.1(2) . . ? O3W Ni1 O2W 175.8(2) . . ? N1 Ni1 O2W 94.6(2) . . ? O1W Ni1 O2W 90.5(2) . . ? N2 Ni1 O2W 93.3(2) . . ? C1 O1 C5 118.4(6) . . ? C11 N1 C15 117.0(7) . . ? C11 N1 Ni1 129.3(5) . . ? C15 N1 Ni1 112.9(5) . . ? C2 C1 O1 122.7(6) . . ? C2 C1 C10 123.2(7) . . ? O1 C1 C10 114.1(6) . . ? C21 N2 C22 117.8(7) . . ? C21 N2 Ni1 130.0(6) . . ? C22 N2 Ni1 112.1(5) . . ? C1 C2 C3 120.7(7) . . ? O3 C3 C4 123.6(7) . . ? O3 C3 C2 122.5(7) . . ? C4 C3 C2 113.9(7) . . ? C5 C4 C3 122.5(7) . . ? C4 C5 O1 121.6(7) . . ? C4 C5 C51 124.9(7) . . ? O1 C5 C51 113.4(7) . . ? O11 C10 O12 128.1(7) . . ? O11 C10 C1 113.1(7) . . ? O12 C10 C1 118.8(7) . . ? C10 O11 Ni1 129.7(5) . . ? N1 C11 C12 123.7(8) . . ? C13 C12 C11 118.8(8) . . ? C12 C13 C14 119.7(8) . . ? C15 C14 C13 117.9(8) . . ? C15 C14 C16 118.8(8) . . ? C13 C14 C16 123.1(8) . . ? N1 C15 C14 122.6(7) . . ? N1 C15 C22 117.1(7) . . ? C14 C15 C22 120.3(7) . . ? C17 C16 C14 120.6(8) . . ? C16 C17 C18 121.6(8) . . ? C19 C18 C22 117.2(8) . . ? C19 C18 C17 124.0(8) . . ? C22 C18 C17 118.9(8) . . ? C20 C19 C18 120.2(8) . . ? C19 C20 C21 119.0(8) . . ? N2 C21 C20 123.1(8) . . ? N2 C22 C18 122.7(7) . . ? N2 C22 C15 117.5(7) . . ? C18 C22 C15 119.7(7) . . ? O52 C51 O51 125.6(7) . . ? O52 C51 C5 120.4(7) . . ? O51 C51 C5 113.9(7) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.883 _refine_diff_density_min -0.803 _refine_diff_density_rms 0.138 #============================================ data_6 _database_code_depnum_ccdc_archive 'CCDC 779946' #TrackingRef '- Mat_dep.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H28.60 N4 O11.30 Zn' _chemical_formula_weight 703.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.634(2) _cell_length_b 12.944(2) _cell_length_c 19.357(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.815(3) _cell_angle_gamma 90.00 _cell_volume 3086.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3251 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.09 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 0.866 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826727 _exptl_absorpt_correction_T_max 1.000000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19126 _diffrn_reflns_av_R_equivalents 0.0820 _diffrn_reflns_av_sigmaI/netI 0.1279 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.03 _reflns_number_total 7285 _reflns_number_gt 3235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1108P)^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 7285 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1651 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2276 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.84494(5) 0.88137(5) 0.76558(3) 0.0423(2) Uani 1 1 d . . . O1W O 0.7854(3) 0.7654(3) 0.69167(18) 0.0496(9) Uani 1 1 d . . . O2W O 0.7549(3) 0.9982(3) 0.70444(19) 0.0550(10) Uani 1 1 d . . . O31 O 0.4576(3) 0.8197(3) 0.13168(17) 0.0434(9) Uani 1 1 d . . . O32 O 0.3858(3) 0.9185(3) 0.2293(2) 0.0522(10) Uani 1 1 d . . . O33 O 0.7718(4) 0.8193(4) 0.1177(3) 0.0911(16) Uani 1 1 d . . . O34 O 0.5375(4) 1.0122(3) 0.2592(2) 0.0710(13) Uani 1 1 d . . . O35 O 0.4193(4) 0.6570(4) -0.0155(2) 0.0777(13) Uani 1 1 d . . . O36 O 0.3150(3) 0.6852(3) 0.0618(2) 0.0640(11) Uani 1 1 d . . . N1 N 0.9876(4) 0.9151(3) 0.7262(2) 0.0406(10) Uani 1 1 d . . . N11 N 0.8831(4) 0.9911(3) 0.8545(2) 0.0484(11) Uani 1 1 d . . . N12 N 0.7236(4) 0.8494(3) 0.8234(2) 0.0446(11) Uani 1 1 d . . . N2 N 0.9666(3) 0.7776(3) 0.8276(2) 0.0384(10) Uani 1 1 d . . . C1 C 0.9951(5) 0.9798(4) 0.6742(3) 0.0469(13) Uani 1 1 d . . . H1 H 0.9334 1.0155 0.6513 0.056 Uiso 1 1 calc R . . C2 C 1.0926(5) 0.9963(4) 0.6526(3) 0.0507(14) Uani 1 1 d . . . H2 H 1.0948 1.0401 0.6148 0.061 Uiso 1 1 calc R . . C3 C 1.1844(5) 0.9469(4) 0.6880(3) 0.0505(14) Uani 1 1 d . . . H3 H 1.2502 0.9580 0.6751 0.061 Uiso 1 1 calc R . . C4 C 1.1790(4) 0.8793(4) 0.7437(3) 0.0418(12) Uani 1 1 d . . . C5 C 1.0782(4) 0.8631(4) 0.7597(3) 0.0371(12) Uani 1 1 d . . . C6 C 1.0659(4) 0.7911(3) 0.8144(2) 0.0351(11) Uani 1 1 d . . . C7 C 1.1570(4) 0.7357(4) 0.8502(3) 0.0432(13) Uani 1 1 d . . . C8 C 1.2605(4) 0.7549(5) 0.8336(3) 0.0529(14) Uani 1 1 d . . . H8 H 1.3215 0.7198 0.8581 0.063 Uiso 1 1 calc R . . C9 C 1.2701(5) 0.8242(5) 0.7821(3) 0.0553(15) Uani 1 1 d . . . H9 H 1.3378 0.8353 0.7720 0.066 Uiso 1 1 calc R . . C10 C 1.1416(5) 0.6625(4) 0.9001(3) 0.0524(14) Uani 1 1 d . . . H10 H 1.1995 0.6231 0.9245 0.063 Uiso 1 1 calc R . . C11 C 1.0409(5) 0.6499(4) 0.9123(3) 0.0512(15) Uani 1 1 d . . . H11 H 1.0294 0.6014 0.9453 0.061 Uiso 1 1 calc R . . C12 C 0.9548(5) 0.7089(4) 0.8757(3) 0.0487(14) Uani 1 1 d . . . H12 H 0.8865 0.6997 0.8855 0.058 Uiso 1 1 calc R . . C13 C 0.9643(5) 1.0587(5) 0.8708(3) 0.0657(17) Uani 1 1 d . . . H13 H 1.0151 1.0616 0.8427 0.079 Uiso 1 1 calc R . . C14 C 0.9755(7) 1.1243(5) 0.9277(4) 0.088(2) Uani 1 1 d . . . H14 H 1.0335 1.1702 0.9380 0.106 Uiso 1 1 calc R . . C15 C 0.9006(7) 1.1217(5) 0.9692(4) 0.088(2) Uani 1 1 d . . . H15 H 0.9078 1.1661 1.0077 0.106 Uiso 1 1 calc R . . C16 C 0.8140(6) 1.0529(5) 0.9541(3) 0.0608(17) Uani 1 1 d . . . C17 C 0.8096(5) 0.9865(4) 0.8959(3) 0.0464(13) Uani 1 1 d . . . C18 C 0.7252(4) 0.9120(4) 0.8791(3) 0.0416(12) Uani 1 1 d . . . C19 C 0.6466(5) 0.9071(5) 0.9200(3) 0.0550(16) Uani 1 1 d . . . C20 C 0.6527(7) 0.9767(6) 0.9779(3) 0.072(2) Uani 1 1 d . . . H20 H 0.5998 0.9737 1.0044 0.087 Uiso 1 1 calc R . . C21 C 0.7323(7) 1.0459(6) 0.9950(3) 0.079(2) Uani 1 1 d . . . H21 H 0.7350 1.0896 1.0335 0.094 Uiso 1 1 calc R . . C22 C 0.5655(5) 0.8303(5) 0.9006(4) 0.0661(18) Uani 1 1 d . . . H22 H 0.5121 0.8231 0.9265 0.079 Uiso 1 1 calc R . . C23 C 0.5653(5) 0.7682(5) 0.8453(4) 0.0658(18) Uani 1 1 d . . . H23 H 0.5114 0.7185 0.8324 0.079 Uiso 1 1 calc R . . C24 C 0.6470(5) 0.7785(5) 0.8070(3) 0.0582(15) Uani 1 1 d . . . H24 H 0.6472 0.7342 0.7692 0.070 Uiso 1 1 calc R . . C31 C 0.5300(4) 0.8835(4) 0.1740(3) 0.0430(12) Uani 1 1 d . . . C32 C 0.6338(5) 0.8852(4) 0.1695(3) 0.0542(15) Uani 1 1 d . . . H32 H 0.6811 0.9298 0.1990 0.065 Uiso 1 1 calc R . . C33 C 0.6758(5) 0.8216(5) 0.1215(4) 0.0633(17) Uani 1 1 d . . . C34 C 0.5937(5) 0.7586(5) 0.0767(3) 0.0548(15) Uani 1 1 d . . . H34 H 0.6131 0.7164 0.0426 0.066 Uiso 1 1 calc R . . C35 C 0.4916(5) 0.7597(4) 0.0832(3) 0.0442(13) Uani 1 1 d . . . C351 C 0.3995(5) 0.6949(4) 0.0391(3) 0.0510(14) Uani 1 1 d . . . C311 C 0.4802(5) 0.9431(4) 0.2255(3) 0.0472(13) Uani 1 1 d . . . O3W O 0.8366(5) 0.6552(5) 0.0264(4) 0.135(2) Uani 1 1 d . . . O4W O 0.1977(7) 0.5121(6) 0.0643(3) 0.180(4) Uani 1 1 d . . . O5W O 0.0116(6) 0.6206(5) 0.1305(4) 0.155(3) Uani 1 1 d . . . O6W O 0.3725(14) 0.4393(14) 0.0165(10) 0.101(6) Uani 0.30 1 d P . . 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 Zn 0.0397(4) 0.0441(4) 0.0444(4) -0.0016(3) 0.0118(3) 0.0012(3) O1W 0.043(2) 0.057(2) 0.052(2) -0.0090(18) 0.0170(18) 0.0051(18) O2W 0.056(2) 0.059(3) 0.051(2) 0.0010(18) 0.0151(19) 0.015(2) O31 0.044(2) 0.044(2) 0.045(2) -0.0017(17) 0.0146(17) -0.0035(17) O32 0.060(3) 0.039(2) 0.061(2) -0.0042(18) 0.022(2) 0.0095(19) O33 0.050(3) 0.110(4) 0.124(4) 0.001(3) 0.041(3) 0.002(3) O34 0.073(3) 0.063(3) 0.077(3) -0.021(2) 0.016(2) -0.016(2) O35 0.093(4) 0.086(3) 0.054(3) -0.021(2) 0.017(3) -0.001(3) O36 0.065(3) 0.077(3) 0.050(2) -0.006(2) 0.013(2) -0.020(2) N1 0.047(3) 0.033(2) 0.040(2) 0.0012(19) 0.007(2) -0.002(2) N11 0.050(3) 0.043(3) 0.050(3) -0.001(2) 0.008(2) -0.006(2) N12 0.046(3) 0.038(2) 0.050(3) -0.003(2) 0.011(2) 0.004(2) N2 0.036(2) 0.036(2) 0.043(2) -0.0026(19) 0.009(2) -0.0047(19) C1 0.047(3) 0.042(3) 0.050(3) 0.006(3) 0.006(3) 0.000(3) C2 0.061(4) 0.043(3) 0.050(3) 0.004(3) 0.015(3) -0.013(3) C3 0.048(3) 0.044(3) 0.061(4) 0.004(3) 0.015(3) -0.010(3) C4 0.034(3) 0.043(3) 0.046(3) 0.000(3) 0.004(2) 0.000(2) C5 0.037(3) 0.034(3) 0.039(3) -0.003(2) 0.007(2) -0.001(2) C6 0.037(3) 0.026(3) 0.041(3) -0.002(2) 0.006(2) -0.002(2) C7 0.046(3) 0.041(3) 0.039(3) -0.005(2) 0.002(2) 0.002(3) C8 0.037(3) 0.057(4) 0.059(4) 0.002(3) -0.002(3) 0.009(3) C9 0.039(3) 0.063(4) 0.062(4) 0.000(3) 0.007(3) -0.002(3) C10 0.059(4) 0.052(3) 0.043(3) 0.004(3) 0.003(3) 0.002(3) C11 0.065(4) 0.046(3) 0.040(3) 0.009(3) 0.006(3) -0.002(3) C12 0.054(3) 0.048(3) 0.046(3) 0.002(3) 0.014(3) -0.006(3) C13 0.071(4) 0.047(4) 0.077(4) -0.011(3) 0.011(4) -0.013(3) C14 0.102(6) 0.058(5) 0.096(6) -0.019(4) 0.003(5) -0.025(4) C15 0.122(7) 0.061(5) 0.077(5) -0.034(4) 0.010(5) -0.009(5) C16 0.081(5) 0.055(4) 0.042(3) -0.007(3) 0.003(3) 0.011(4) C17 0.059(4) 0.039(3) 0.043(3) 0.000(2) 0.014(3) 0.004(3) C18 0.040(3) 0.044(3) 0.043(3) 0.006(2) 0.012(2) 0.007(2) C19 0.063(4) 0.056(4) 0.051(3) 0.012(3) 0.022(3) 0.019(3) C20 0.099(6) 0.075(5) 0.053(4) 0.012(4) 0.038(4) 0.025(4) C21 0.112(6) 0.079(5) 0.050(4) -0.008(4) 0.030(4) 0.028(5) C22 0.055(4) 0.079(5) 0.073(4) 0.023(4) 0.033(4) 0.012(4) C23 0.046(4) 0.065(4) 0.092(5) 0.012(4) 0.027(4) -0.005(3) C24 0.055(4) 0.052(4) 0.068(4) -0.003(3) 0.013(3) -0.004(3) C31 0.050(3) 0.036(3) 0.042(3) 0.005(2) 0.008(3) 0.002(3) C32 0.039(3) 0.055(4) 0.067(4) 0.004(3) 0.011(3) -0.008(3) C33 0.053(4) 0.070(4) 0.074(4) 0.008(4) 0.027(4) 0.010(3) C34 0.064(4) 0.057(4) 0.051(3) 0.003(3) 0.028(3) 0.010(3) C35 0.056(3) 0.044(3) 0.036(3) 0.004(2) 0.017(3) 0.007(3) C351 0.070(4) 0.045(3) 0.037(3) 0.002(3) 0.010(3) 0.004(3) C311 0.052(4) 0.036(3) 0.055(3) 0.007(3) 0.016(3) 0.006(3) O3W 0.099(5) 0.139(5) 0.160(6) -0.011(5) 0.016(4) -0.012(4) O4W 0.247(9) 0.216(8) 0.058(3) 0.025(4) -0.008(4) -0.157(7) O5W 0.137(6) 0.138(6) 0.173(7) 0.085(5) -0.002(5) -0.015(4) O6W 0.097(14) 0.098(13) 0.108(13) -0.028(11) 0.024(11) -0.023(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn O1W 2.095(4) . ? Zn O2W 2.094(4) . ? Zn N12 2.130(4) . ? Zn N1 2.152(4) . ? Zn N2 2.189(4) . ? Zn N11 2.201(4) . ? O31 C35 1.360(6) . ? O31 C31 1.362(6) . ? O32 C311 1.252(6) . ? O33 C33 1.232(7) . ? O34 C311 1.242(7) . ? O35 C351 1.239(6) . ? O36 C351 1.248(7) . ? N1 C1 1.329(6) . ? N1 C5 1.362(6) . ? N11 C13 1.332(7) . ? N11 C17 1.355(7) . ? N12 C24 1.321(7) . ? N12 C18 1.346(6) . ? N2 C12 1.320(6) . ? N2 C6 1.346(6) . ? C1 C2 1.403(7) . ? C2 C3 1.368(7) . ? C3 C4 1.402(7) . ? C4 C5 1.392(7) . ? C4 C9 1.416(7) . ? C5 C6 1.444(6) . ? C6 C7 1.402(7) . ? C7 C10 1.396(7) . ? C7 C8 1.436(7) . ? C8 C9 1.367(8) . ? C10 C11 1.355(8) . ? C11 C12 1.388(8) . ? C13 C14 1.372(9) . ? C14 C15 1.371(11) . ? C15 C16 1.390(10) . ? C16 C17 1.408(7) . ? C16 C21 1.437(9) . ? C17 C18 1.421(7) . ? C18 C19 1.402(7) . ? C19 C22 1.416(9) . ? C19 C20 1.427(9) . ? C20 C21 1.332(10) . ? C22 C23 1.338(9) . ? C23 C24 1.405(8) . ? C31 C32 1.334(7) . ? C31 C311 1.505(7) . ? C32 C33 1.428(8) . ? C33 C34 1.447(9) . ? C34 C35 1.324(7) . ? C35 C351 1.531(8) . ? 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 O1W Zn O2W 93.64(15) . . ? O1W Zn N12 91.62(15) . . ? O2W Zn N12 94.21(16) . . ? O1W Zn N1 96.09(14) . . ? O2W Zn N1 92.64(15) . . ? N12 Zn N1 169.33(16) . . ? O1W Zn N2 92.12(14) . . ? O2W Zn N2 168.74(15) . . ? N12 Zn N2 95.29(16) . . ? N1 Zn N2 77.12(15) . . ? O1W Zn N11 168.40(15) . . ? O2W Zn N11 88.48(15) . . ? N12 Zn N11 76.84(17) . . ? N1 Zn N11 95.20(16) . . ? N2 Zn N11 87.81(16) . . ? C35 O31 C31 119.2(4) . . ? C1 N1 C5 118.6(5) . . ? C1 N1 Zn 127.0(4) . . ? C5 N1 Zn 114.4(3) . . ? C13 N11 C17 118.7(5) . . ? C13 N11 Zn 129.3(4) . . ? C17 N11 Zn 112.0(3) . . ? C24 N12 C18 119.4(5) . . ? C24 N12 Zn 125.6(4) . . ? C18 N12 Zn 114.8(4) . . ? C12 N2 C6 118.6(4) . . ? C12 N2 Zn 128.7(4) . . ? C6 N2 Zn 112.7(3) . . ? N1 C1 C2 122.5(5) . . ? C3 C2 C1 118.8(5) . . ? C2 C3 C4 119.8(5) . . ? C5 C4 C3 118.0(5) . . ? C5 C4 C9 118.9(5) . . ? C3 C4 C9 123.1(5) . . ? N1 C5 C4 122.2(4) . . ? N1 C5 C6 116.9(4) . . ? C4 C5 C6 120.9(5) . . ? N2 C6 C7 122.4(4) . . ? N2 C6 C5 118.7(4) . . ? C7 C6 C5 118.8(5) . . ? C10 C7 C6 117.7(5) . . ? C10 C7 C8 123.0(5) . . ? C6 C7 C8 119.3(5) . . ? C9 C8 C7 120.7(5) . . ? C8 C9 C4 121.4(5) . . ? C11 C10 C7 118.9(5) . . ? C10 C11 C12 120.3(5) . . ? N2 C12 C11 122.1(5) . . ? N11 C13 C14 122.3(7) . . ? C13 C14 C15 119.6(7) . . ? C14 C15 C16 120.3(6) . . ? C15 C16 C17 116.7(6) . . ? C15 C16 C21 123.5(6) . . ? C17 C16 C21 119.7(6) . . ? N11 C17 C16 122.4(6) . . ? N11 C17 C18 118.2(5) . . ? C16 C17 C18 119.4(5) . . ? N12 C18 C19 122.5(5) . . ? N12 C18 C17 117.9(5) . . ? C19 C18 C17 119.5(5) . . ? C18 C19 C22 116.4(5) . . ? C18 C19 C20 119.4(6) . . ? C22 C19 C20 124.2(6) . . ? C21 C20 C19 121.8(6) . . ? C20 C21 C16 120.0(6) . . ? C23 C22 C19 120.4(6) . . ? C22 C23 C24 119.6(6) . . ? N12 C24 C23 121.6(6) . . ? C32 C31 O31 120.7(5) . . ? C32 C31 C311 126.6(5) . . ? O31 C31 C311 112.6(5) . . ? C31 C32 C33 123.1(6) . . ? O33 C33 C32 124.5(7) . . ? O33 C33 C34 122.3(6) . . ? C32 C33 C34 113.2(5) . . ? C35 C34 C33 121.4(5) . . ? C34 C35 O31 122.4(5) . . ? C34 C35 C351 125.2(5) . . ? O31 C35 C351 112.4(5) . . ? O35 C351 O36 127.7(6) . . ? O35 C351 C35 114.8(6) . . ? O36 C351 C35 117.5(5) . . ? O32 C311 O34 127.2(5) . . ? O32 C311 C31 116.9(5) . . ? O34 C311 C31 115.9(5) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.660 _refine_diff_density_min -1.211 _refine_diff_density_rms 0.095 #============================================