# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prof. Chong-Bo Liu' _publ_contact_author_email cbliu2002@163.com loop_ _publ_author_name 'Yun-Nan Gong' 'Chong-Bo Liu' 'Hui-Liang Wen' 'Zhi-Qiang Xiong' ; Liang Ding ; data_1 _database_code_depnum_ccdc_archive 'CCDC 799349' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N4 Ni O6' _chemical_formula_weight 469.09 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)/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 4.8445(9) _cell_length_b 32.906(6) _cell_length_c 6.2836(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.406(2) _cell_angle_gamma 90.00 _cell_volume 965.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 2058 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.12 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.053 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7114 _exptl_absorpt_correction_T_max 0.8421 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8567 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2212 _reflns_number_gt 1725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0552P)^2^+0.7610P] 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 2212 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.5000 0.0000 0.0000 0.02559(6) Uani 1 2 d S . . O1 O 0.3363(2) 0.01825(3) 0.25732(15) 0.0285(2) Uani 1 1 d . . . O2 O 0.3464(2) 0.06954(3) 0.49311(16) 0.0373(3) Uani 1 1 d . . . O3 O 0.1419(2) 0.02783(3) -0.22653(15) 0.0293(3) Uani 1 1 d . . . H1W H 0.1949 0.0362 -0.3315 0.044 Uiso 1 1 d R . . H2W H 0.0157 0.0108 -0.2674 0.044 Uiso 1 1 d R . . N1 N 0.6803(2) 0.05523(4) 0.06525(18) 0.0273(3) Uani 1 1 d . . . N2 N 0.8382(2) 0.08082(4) -0.01858(19) 0.0292(3) Uani 1 1 d . . . H2 H 0.9149 0.0746 -0.1230 0.035 Uiso 1 1 calc R . . C1 C 0.4131(3) 0.05338(4) 0.3355(2) 0.0263(4) Uani 1 1 d . . . C2 C 0.6006(3) 0.07620(4) 0.2209(2) 0.0256(3) Uani 1 1 d . . . C3 C 0.7089(3) 0.11535(5) 0.2370(2) 0.0298(4) Uani 1 1 d . . . H3 H 0.6837 0.1358 0.3324 0.036 Uiso 1 1 calc R . . C4 C 0.8631(3) 0.11758(4) 0.0800(2) 0.0276(4) Uani 1 1 d . . . C5 C 1.0280(3) 0.15063(5) 0.0160(3) 0.0334(4) Uani 1 1 d . . . C6 C 1.0842(4) 0.18559(5) 0.1394(3) 0.0515(6) Uani 1 1 d . . . H6 H 1.0113 0.1885 0.2613 0.062 Uiso 1 1 calc R . . C7 C 1.2475(5) 0.21654(6) 0.0856(4) 0.0704(7) Uani 1 1 d . . . H7 H 1.2867 0.2398 0.1725 0.085 Uiso 1 1 calc R . . C8 C 1.3503(5) 0.21275(6) -0.0954(4) 0.0740(7) Uani 1 1 d . . . H8 H 1.4595 0.2335 -0.1323 0.089 Uiso 1 1 calc R . . C9 C 1.2934(4) 0.17856(6) -0.2226(3) 0.0606(6) Uani 1 1 d . . . H9 H 1.3634 0.1764 -0.3463 0.073 Uiso 1 1 calc R . . C10 C 1.1338(4) 0.14720(6) -0.1706(3) 0.0453(5) Uani 1 1 d . . . H10 H 1.0967 0.1240 -0.2583 0.054 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 Ni1 0.02763(11) 0.02945(12) 0.02371(10) -0.00305(10) 0.01384(8) -0.00549(11) O1 0.0280(4) 0.0346(5) 0.0274(4) -0.0020(4) 0.0155(3) -0.0057(4) O2 0.0496(6) 0.0392(6) 0.0318(5) -0.0021(4) 0.0259(4) -0.0012(5) O3 0.0277(4) 0.0386(6) 0.0259(4) 0.0004(4) 0.0147(4) -0.0049(4) N1 0.0270(5) 0.0334(6) 0.0262(5) -0.0020(5) 0.0154(4) -0.0058(5) N2 0.0311(5) 0.0340(6) 0.0284(5) -0.0021(5) 0.0179(4) -0.0055(5) C1 0.0251(6) 0.0351(7) 0.0213(6) 0.0033(5) 0.0107(5) 0.0017(6) C2 0.0262(6) 0.0314(7) 0.0214(6) 0.0005(5) 0.0100(5) 0.0024(5) C3 0.0298(6) 0.0337(8) 0.0291(6) -0.0026(6) 0.0135(5) 0.0002(6) C4 0.0253(6) 0.0305(7) 0.0280(6) 0.0016(6) 0.0087(5) -0.0009(6) C5 0.0273(7) 0.0322(7) 0.0421(7) 0.0070(6) 0.0115(6) 0.0002(6) C6 0.0499(9) 0.0376(9) 0.0744(11) -0.0066(9) 0.0296(8) -0.0079(8) C7 0.0679(12) 0.0375(10) 0.1167(16) -0.0076(11) 0.0435(11) -0.0150(9) C8 0.0639(11) 0.0477(11) 0.1217(16) 0.0268(11) 0.0447(11) -0.0077(10) C9 0.0582(10) 0.0688(12) 0.0622(10) 0.0257(9) 0.0288(8) -0.0032(10) C10 0.0476(9) 0.0513(10) 0.0400(8) 0.0091(7) 0.0171(7) -0.0046(8) _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 N1 2.0110(12) . ? Ni1 N1 2.0110(12) 3_655 ? Ni1 O1 2.0702(11) . ? Ni1 O1 2.0702(11) 3_655 ? Ni1 O3 2.1359(9) 3_655 ? Ni1 O3 2.1359(9) . ? O1 C1 1.2723(17) . ? O2 C1 1.2403(18) . ? O3 H1W 0.8165 . ? O3 H2W 0.8189 . ? N1 C2 1.3348(19) . ? N1 N2 1.3363(18) . ? N2 C4 1.3498(19) . ? N2 H2 0.8600 . ? C1 C2 1.502(2) . ? C2 C3 1.385(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9300 . ? C4 C5 1.467(2) . ? C5 C6 1.373(2) . ? C5 C10 1.403(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 C8 1.363(4) . ? C7 H7 0.9300 . ? C8 C9 1.365(3) . ? C8 H8 0.9300 . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 H10 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 N1 Ni1 N1 180.00(3) . 3_655 ? N1 Ni1 O1 79.30(5) . . ? N1 Ni1 O1 100.70(5) 3_655 . ? N1 Ni1 O1 100.70(5) . 3_655 ? N1 Ni1 O1 79.30(5) 3_655 3_655 ? O1 Ni1 O1 180.00(7) . 3_655 ? N1 Ni1 O3 91.13(4) . 3_655 ? N1 Ni1 O3 88.87(4) 3_655 3_655 ? O1 Ni1 O3 90.90(4) . 3_655 ? O1 Ni1 O3 89.10(4) 3_655 3_655 ? N1 Ni1 O3 88.87(4) . . ? N1 Ni1 O3 91.13(4) 3_655 . ? O1 Ni1 O3 89.10(4) . . ? O1 Ni1 O3 90.90(4) 3_655 . ? O3 Ni1 O3 180.00(5) 3_655 . ? C1 O1 Ni1 115.57(9) . . ? Ni1 O3 H1W 108.0 . . ? Ni1 O3 H2W 108.8 . . ? H1W O3 H2W 110.2 . . ? C2 N1 N2 105.68(12) . . ? C2 N1 Ni1 114.97(10) . . ? N2 N1 Ni1 138.78(10) . . ? N1 N2 C4 111.99(13) . . ? N1 N2 H2 124.0 . . ? C4 N2 H2 124.0 . . ? O2 C1 O1 125.89(14) . . ? O2 C1 C2 119.19(13) . . ? O1 C1 C2 114.92(12) . . ? N1 C2 C3 110.91(13) . . ? N1 C2 C1 114.98(12) . . ? C3 C2 C1 134.10(14) . . ? C2 C3 C4 105.20(13) . . ? C2 C3 H3 127.4 . . ? C4 C3 H3 127.4 . . ? N2 C4 C3 106.23(13) . . ? N2 C4 C5 121.81(14) . . ? C3 C4 C5 131.96(14) . . ? C6 C5 C10 118.51(17) . . ? C6 C5 C4 120.46(16) . . ? C10 C5 C4 121.03(15) . . ? C5 C6 C7 121.2(2) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 119.7(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 121.1(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C5 119.33(18) . . ? C9 C10 H10 120.3 . . ? C5 C10 H10 120.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 O1 C1 0.48(9) . . . . ? N1 Ni1 O1 C1 -179.52(9) 3_655 . . . ? O1 Ni1 O1 C1 -104.00(14) 3_655 . . . ? O3 Ni1 O1 C1 91.46(9) 3_655 . . . ? O3 Ni1 O1 C1 -88.54(9) . . . . ? N1 Ni1 N1 C2 143(100) 3_655 . . . ? O1 Ni1 N1 C2 -3.52(9) . . . . ? O1 Ni1 N1 C2 176.48(9) 3_655 . . . ? O3 Ni1 N1 C2 -94.23(9) 3_655 . . . ? O3 Ni1 N1 C2 85.77(9) . . . . ? N1 Ni1 N1 N2 -26(100) 3_655 . . . ? O1 Ni1 N1 N2 -173.26(14) . . . . ? O1 Ni1 N1 N2 6.74(14) 3_655 . . . ? O3 Ni1 N1 N2 96.04(13) 3_655 . . . ? O3 Ni1 N1 N2 -83.96(13) . . . . ? C2 N1 N2 C4 0.33(14) . . . . ? Ni1 N1 N2 C4 170.67(10) . . . . ? Ni1 O1 C1 O2 -177.82(11) . . . . ? Ni1 O1 C1 C2 2.32(14) . . . . ? N2 N1 C2 C3 -0.17(14) . . . . ? Ni1 N1 C2 C3 -173.17(9) . . . . ? N2 N1 C2 C1 178.71(10) . . . . ? Ni1 N1 C2 C1 5.71(14) . . . . ? O2 C1 C2 N1 174.78(12) . . . . ? O1 C1 C2 N1 -5.35(16) . . . . ? O2 C1 C2 C3 -6.7(2) . . . . ? O1 C1 C2 C3 173.19(14) . . . . ? N1 C2 C3 C4 -0.03(15) . . . . ? C1 C2 C3 C4 -178.62(13) . . . . ? N1 N2 C4 C3 -0.35(15) . . . . ? N1 N2 C4 C5 179.74(11) . . . . ? C2 C3 C4 N2 0.22(14) . . . . ? C2 C3 C4 C5 -179.88(14) . . . . ? N2 C4 C5 C6 -170.59(14) . . . . ? C3 C4 C5 C6 9.5(2) . . . . ? N2 C4 C5 C10 8.9(2) . . . . ? C3 C4 C5 C10 -171.03(15) . . . . ? C10 C5 C6 C7 -1.6(3) . . . . ? C4 C5 C6 C7 177.86(16) . . . . ? C5 C6 C7 C8 1.3(3) . . . . ? C6 C7 C8 C9 -0.2(3) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? C8 C9 C10 C5 0.1(3) . . . . ? C6 C5 C10 C9 0.9(2) . . . . ? C4 C5 C10 C9 -178.55(15) . . . . ? 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 O3 H2W O1 0.82 1.97 2.7323(14) 154.5 3 O3 H1W O2 0.82 1.84 2.6261(15) 161.0 1_554 N2 H2 O3 0.86 2.09 2.8169(17) 141.4 1_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.670 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.075 data_2 _database_code_depnum_ccdc_archive 'CCDC 799350' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Cu N4 O6' _chemical_formula_weight 473.92 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)/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 5.0443(6) _cell_length_b 32.161(4) _cell_length_c 6.3234(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.2930(10) _cell_angle_gamma 90.00 _cell_volume 984.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 2772 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.60 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 486 _exptl_absorpt_coefficient_mu 1.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6897 _exptl_absorpt_correction_T_max 0.8285 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8611 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2254 _reflns_number_gt 1907 _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^)+(0.0302P)^2^+0.7200P] 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 2254 _refine_ls_number_parameters 150 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.077 _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 Cu1 Cu 0.5000 0.0000 0.0000 0.03166(13) Uani 1 2 d S . . O1 O 0.3462(3) 0.01796(5) 0.2440(2) 0.0325(3) Uani 1 1 d . . . O2 O 0.3301(4) 0.07235(5) 0.4604(3) 0.0404(4) Uani 1 1 d . . . O3 O 0.0850(4) 0.03336(6) -0.2706(3) 0.0380(4) Uani 1 1 d D . . N1 N 0.6670(4) 0.05536(5) 0.0513(3) 0.0294(4) Uani 1 1 d . . . N2 N 0.8212(4) 0.08034(5) -0.0348(3) 0.0301(4) Uani 1 1 d . . . H2 H 0.8956 0.0730 -0.1359 0.036 Uiso 1 1 calc R . . C1 C 0.4084(4) 0.05525(7) 0.3144(3) 0.0288(5) Uani 1 1 d . . . C2 C 0.5895(4) 0.07783(7) 0.2015(3) 0.0277(4) Uani 1 1 d . . . C3 C 0.6964(4) 0.11779(7) 0.2111(4) 0.0302(5) Uani 1 1 d . . . H3 H 0.6732 0.1395 0.3017 0.036 Uiso 1 1 calc R . . C4 C 0.8454(4) 0.11852(6) 0.0569(4) 0.0282(4) Uani 1 1 d . . . C5 C 1.0091(5) 0.15138(7) -0.0085(4) 0.0328(5) Uani 1 1 d . . . C6 C 1.0740(6) 0.18727(8) 0.1155(5) 0.0473(6) Uani 1 1 d . . . H6 H 1.0067 0.1911 0.2368 0.057 Uiso 1 1 calc R . . C7 C 1.2389(7) 0.21770(9) 0.0605(6) 0.0641(9) Uani 1 1 d . . . H7 H 1.2821 0.2417 0.1454 0.077 Uiso 1 1 calc R . . C8 C 1.3376(6) 0.21240(9) -0.1183(6) 0.0642(9) Uani 1 1 d . . . H8 H 1.4482 0.2328 -0.1543 0.077 Uiso 1 1 calc R . . C9 C 1.2744(6) 0.17720(10) -0.2448(5) 0.0565(8) Uani 1 1 d . . . H9 H 1.3419 0.1738 -0.3663 0.068 Uiso 1 1 calc R . . C10 C 1.1097(5) 0.14664(8) -0.1918(4) 0.0438(6) Uani 1 1 d . . . H10 H 1.0662 0.1229 -0.2786 0.053 Uiso 1 1 calc R . . H1W H 0.138(6) 0.0417(9) -0.376(4) 0.069(10) Uiso 1 1 d D . . H2W H -0.041(5) 0.0163(8) -0.312(5) 0.075(11) 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 Cu1 0.0386(2) 0.0297(2) 0.0341(2) -0.00583(17) 0.02227(17) -0.00911(17) O1 0.0365(9) 0.0338(8) 0.0339(8) -0.0019(7) 0.0207(7) -0.0071(7) O2 0.0523(11) 0.0407(9) 0.0388(9) -0.0036(7) 0.0301(8) -0.0031(8) O3 0.0416(10) 0.0443(10) 0.0361(9) -0.0051(8) 0.0239(8) -0.0093(8) N1 0.0332(10) 0.0304(10) 0.0301(9) -0.0028(7) 0.0177(8) -0.0060(7) N2 0.0334(10) 0.0325(10) 0.0311(10) -0.0029(8) 0.0203(8) -0.0064(8) C1 0.0276(11) 0.0349(12) 0.0264(11) 0.0032(9) 0.0115(9) 0.0006(9) C2 0.0286(11) 0.0311(11) 0.0260(10) -0.0003(8) 0.0119(9) 0.0004(8) C3 0.0315(11) 0.0298(11) 0.0320(12) -0.0033(9) 0.0133(9) 0.0002(9) C4 0.0282(10) 0.0277(11) 0.0296(11) 0.0016(9) 0.0094(9) 0.0005(8) C5 0.0285(11) 0.0303(11) 0.0402(12) 0.0071(10) 0.0108(9) 0.0008(9) C6 0.0478(15) 0.0366(14) 0.0641(18) -0.0051(12) 0.0264(13) -0.0063(11) C7 0.0610(19) 0.0357(15) 0.104(3) -0.0046(15) 0.0363(19) -0.0135(13) C8 0.0521(18) 0.0476(17) 0.101(3) 0.0248(17) 0.0345(18) -0.0060(14) C9 0.0530(17) 0.0655(19) 0.0588(18) 0.0232(15) 0.0287(14) -0.0018(14) C10 0.0481(15) 0.0462(15) 0.0411(14) 0.0055(11) 0.0189(12) -0.0060(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 Cu1 N1 1.9572(17) . ? Cu1 N1 1.9573(17) 3_655 ? Cu1 O1 1.9968(14) 3_655 ? Cu1 O1 1.9968(14) . ? Cu1 O3 2.5400(19) . ? O1 C1 1.287(3) . ? O2 C1 1.231(3) . ? O3 H1W 0.827(10) . ? O3 H2W 0.825(10) . ? N1 C2 1.336(3) . ? N1 N2 1.336(2) . ? N2 C4 1.349(3) . ? N2 H2 0.8600 . ? C1 C2 1.496(3) . ? C2 C3 1.388(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.470(3) . ? C5 C6 1.382(3) . ? C5 C10 1.398(3) . ? C6 C7 1.390(4) . ? C6 H6 0.9300 . ? C7 C8 1.368(5) . ? C7 H7 0.9300 . ? C8 C9 1.371(5) . ? C8 H8 0.9300 . ? C9 C10 1.387(3) . ? C9 H9 0.9300 . ? C10 H10 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 N1 Cu1 N1 180.0 . 3_655 ? N1 Cu1 O1 98.56(6) . 3_655 ? N1 Cu1 O1 81.44(6) 3_655 3_655 ? N1 Cu1 O1 81.44(6) . . ? N1 Cu1 O1 98.56(6) 3_655 . ? O1 Cu1 O1 180.0 3_655 . ? N1 Cu1 O3 87.85(7) . . ? N1 Cu1 O3 92.15(7) 3_655 . ? O1 Cu1 O3 91.56(6) 3_655 . ? O1 Cu1 O3 88.44(6) . . ? C1 O1 Cu1 115.29(13) . . ? Cu1 O3 H1W 107(2) . . ? Cu1 O3 H2W 110(2) . . ? H1W O3 H2W 111(2) . . ? C2 N1 N2 106.51(17) . . ? C2 N1 Cu1 114.33(14) . . ? N2 N1 Cu1 138.77(14) . . ? N1 N2 C4 111.41(17) . . ? N1 N2 H2 124.3 . . ? C4 N2 H2 124.3 . . ? O2 C1 O1 125.27(19) . . ? O2 C1 C2 120.58(19) . . ? O1 C1 C2 114.14(18) . . ? N1 C2 C3 110.16(18) . . ? N1 C2 C1 114.60(18) . . ? C3 C2 C1 135.23(19) . . ? C4 C3 C2 105.36(19) . . ? C4 C3 H3 127.3 . . ? C2 C3 H3 127.3 . . ? N2 C4 C3 106.56(18) . . ? N2 C4 C5 121.60(19) . . ? C3 C4 C5 131.8(2) . . ? C6 C5 C10 118.6(2) . . ? C6 C5 C4 120.2(2) . . ? C10 C5 C4 121.2(2) . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 120.3(3) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 O1 C1 2.75(15) . . . . ? N1 Cu1 O1 C1 -177.25(15) 3_655 . . . ? O1 Cu1 O1 C1 -14(3) 3_655 . . . ? O3 Cu1 O1 C1 -85.31(15) . . . . ? N1 Cu1 N1 C2 -81(3) 3_655 . . . ? O1 Cu1 N1 C2 175.94(15) 3_655 . . . ? O1 Cu1 N1 C2 -4.06(15) . . . . ? O3 Cu1 N1 C2 84.69(16) . . . . ? N1 Cu1 N1 N2 108(3) 3_655 . . . ? O1 Cu1 N1 N2 4.4(2) 3_655 . . . ? O1 Cu1 N1 N2 -175.6(2) . . . . ? O3 Cu1 N1 N2 -86.8(2) . . . . ? C2 N1 N2 C4 0.1(2) . . . . ? Cu1 N1 N2 C4 172.02(17) . . . . ? Cu1 O1 C1 O2 178.61(18) . . . . ? Cu1 O1 C1 C2 -1.0(2) . . . . ? N2 N1 C2 C3 0.0(2) . . . . ? Cu1 N1 C2 C3 -174.22(15) . . . . ? N2 N1 C2 C1 178.84(17) . . . . ? Cu1 N1 C2 C1 4.7(2) . . . . ? O2 C1 C2 N1 178.0(2) . . . . ? O1 C1 C2 N1 -2.4(3) . . . . ? O2 C1 C2 C3 -3.5(4) . . . . ? O1 C1 C2 C3 176.1(2) . . . . ? N1 C2 C3 C4 0.0(2) . . . . ? C1 C2 C3 C4 -178.6(2) . . . . ? N1 N2 C4 C3 -0.1(2) . . . . ? N1 N2 C4 C5 179.06(19) . . . . ? C2 C3 C4 N2 0.1(2) . . . . ? C2 C3 C4 C5 -179.0(2) . . . . ? N2 C4 C5 C6 -167.6(2) . . . . ? C3 C4 C5 C6 11.3(4) . . . . ? N2 C4 C5 C10 10.3(3) . . . . ? C3 C4 C5 C10 -170.8(2) . . . . ? C10 C5 C6 C7 -0.8(4) . . . . ? C4 C5 C6 C7 177.2(3) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? C8 C9 C10 C5 -0.5(4) . . . . ? C6 C5 C10 C9 0.9(4) . . . . ? C4 C5 C10 C9 -177.1(2) . . . . ? 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 N2 H2 O3 0.86 1.93 2.719(2) 152.0 1_655 O3 H1W O2 0.827(10) 1.884(13) 2.678(2) 161(3) 1_554 O3 H2W O1 0.825(10) 2.033(17) 2.773(2) 149(3) 3 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.340 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.053 data_3 _database_code_depnum_ccdc_archive 'CCDC 799351' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N4 O4 Zn' _chemical_formula_weight 439.72 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 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 7.0960(12) _cell_length_b 12.071(2) _cell_length_c 22.767(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.338(3) _cell_angle_gamma 90.00 _cell_volume 1950.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1042 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 19.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7551 _exptl_absorpt_correction_T_max 0.9622 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10603 _diffrn_reflns_av_R_equivalents 0.0816 _diffrn_reflns_av_sigmaI/netI 0.1016 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3626 _reflns_number_gt 2229 _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^)+(0.0365P)^2^+5.7258P] 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 3626 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.23648(9) 0.47885(6) 0.48398(3) 0.0318(2) Uani 1 1 d . . . O1 O -0.0391(5) 0.4025(3) 0.49346(19) 0.0393(11) Uani 1 1 d . . . O2 O -0.2031(6) 0.2466(4) 0.4846(2) 0.0586(14) Uani 1 1 d . . . O3 O 0.5887(5) 0.4889(4) 0.45113(17) 0.0405(11) Uani 1 1 d . . . O4 O 0.7526(6) 0.5699(5) 0.3805(2) 0.0627(15) Uani 1 1 d . . . N1 N 0.2801(6) 0.3070(4) 0.4707(2) 0.0316(12) Uani 1 1 d . . . N2 N 0.4203(6) 0.2409(4) 0.4527(2) 0.0374(13) Uani 1 1 d . . . H2 H 0.5358 0.2616 0.4499 0.045 Uiso 1 1 calc R . . N3 N 0.2627(6) 0.5420(4) 0.3987(2) 0.0321(12) Uani 1 1 d . . . N4 N 0.1245(7) 0.5840(4) 0.3641(2) 0.0365(13) Uani 1 1 d . . . H4 H 0.0064 0.5820 0.3723 0.044 Uiso 1 1 calc R . . C1 C -0.0560(8) 0.2984(5) 0.4837(3) 0.0348(15) Uani 1 1 d . . . C2 C 0.1263(8) 0.2439(5) 0.4689(3) 0.0337(15) Uani 1 1 d . . . C3 C 0.1680(8) 0.1367(5) 0.4509(3) 0.0430(17) Uani 1 1 d . . . H3 H 0.0851 0.0774 0.4473 0.052 Uiso 1 1 calc R . . C4 C 0.3585(8) 0.1373(5) 0.4396(3) 0.0397(16) Uani 1 1 d . . . C5 C 0.4821(9) 0.0489(5) 0.4169(3) 0.0436(17) Uani 1 1 d . . . C6 C 0.4345(11) -0.0595(6) 0.4263(3) 0.060(2) Uani 1 1 d . . . H6 H 0.3277 -0.0766 0.4480 0.072 Uiso 1 1 calc R . . C7 C 0.5450(14) -0.1439(7) 0.4037(4) 0.078(3) Uani 1 1 d . . . H7 H 0.5120 -0.2174 0.4104 0.093 Uiso 1 1 calc R . . C8 C 0.7030(15) -0.1197(9) 0.3716(4) 0.091(3) Uani 1 1 d . . . H8 H 0.7777 -0.1764 0.3568 0.110 Uiso 1 1 calc R . . C9 C 0.7492(12) -0.0118(8) 0.3617(4) 0.086(3) Uani 1 1 d . . . H9 H 0.8554 0.0050 0.3396 0.103 Uiso 1 1 calc R . . C10 C 0.6395(10) 0.0731(7) 0.3841(3) 0.063(2) Uani 1 1 d . . . H10 H 0.6721 0.1465 0.3769 0.075 Uiso 1 1 calc R . . C11 C 0.6035(7) 0.5378(5) 0.4013(3) 0.0364(16) Uani 1 1 d . . . C12 C 0.4227(7) 0.5618(5) 0.3719(3) 0.0319(14) Uani 1 1 d . . . C13 C 0.3901(8) 0.6158(6) 0.3185(3) 0.0498(19) Uani 1 1 d . . . H13 H 0.4797 0.6378 0.2912 0.060 Uiso 1 1 calc R . . C14 C 0.1979(8) 0.6297(6) 0.3147(3) 0.0409(17) Uani 1 1 d . . . C15 C 0.0818(9) 0.6858(6) 0.2696(3) 0.0492(19) Uani 1 1 d . . . C16 C -0.0936(10) 0.6496(8) 0.2546(3) 0.072(3) Uani 1 1 d . . . H16 H -0.1448 0.5886 0.2737 0.087 Uiso 1 1 calc R . . C17 C -0.1973(11) 0.7034(9) 0.2107(3) 0.081(3) Uani 1 1 d . . . H17 H -0.3170 0.6783 0.2005 0.097 Uiso 1 1 calc R . . C18 C -0.1216(14) 0.7929(9) 0.1830(4) 0.090(3) Uani 1 1 d . . . H18 H -0.1924 0.8316 0.1553 0.108 Uiso 1 1 calc R . . C19 C 0.0542(15) 0.8252(8) 0.1955(4) 0.093(3) Uani 1 1 d . . . H19 H 0.1077 0.8829 0.1743 0.112 Uiso 1 1 calc R . . C20 C 0.1582(12) 0.7744(7) 0.2396(4) 0.080(3) Uani 1 1 d . . . H20 H 0.2784 0.7997 0.2489 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0236(3) 0.0307(4) 0.0412(4) -0.0012(4) 0.0008(3) -0.0010(3) O1 0.035(2) 0.025(3) 0.058(3) -0.004(2) -0.002(2) -0.0006(19) O2 0.025(2) 0.047(3) 0.103(4) -0.005(3) 0.006(3) -0.011(2) O3 0.044(2) 0.050(3) 0.028(3) 0.008(2) -0.0065(19) -0.013(2) O4 0.025(2) 0.104(4) 0.060(3) 0.023(3) 0.006(2) -0.004(2) N1 0.022(2) 0.032(3) 0.041(3) -0.006(2) -0.004(2) 0.001(2) N2 0.027(3) 0.026(3) 0.059(4) -0.001(3) 0.001(3) -0.001(2) N3 0.021(2) 0.038(3) 0.037(3) 0.001(3) -0.009(2) 0.001(2) N4 0.028(3) 0.047(3) 0.035(3) 0.004(3) -0.001(2) 0.001(2) C1 0.030(3) 0.041(4) 0.034(4) 0.002(3) -0.006(3) -0.007(3) C2 0.029(3) 0.029(4) 0.043(4) 0.000(3) -0.002(3) -0.008(3) C3 0.036(3) 0.026(4) 0.067(5) -0.004(3) -0.003(3) -0.008(3) C4 0.036(3) 0.032(4) 0.051(5) -0.002(3) -0.008(3) -0.005(3) C5 0.049(4) 0.025(4) 0.056(5) -0.012(3) 0.000(3) 0.005(3) C6 0.079(5) 0.036(4) 0.064(6) -0.004(4) 0.002(4) 0.003(4) C7 0.106(7) 0.039(5) 0.088(7) -0.016(5) -0.002(6) 0.026(5) C8 0.106(8) 0.076(8) 0.092(8) -0.023(6) 0.015(6) 0.042(6) C9 0.075(6) 0.074(7) 0.108(8) -0.026(6) 0.032(5) 0.012(5) C10 0.058(5) 0.055(5) 0.075(6) -0.013(4) 0.017(4) 0.001(4) C11 0.023(3) 0.048(4) 0.037(4) -0.006(3) -0.008(3) 0.003(3) C12 0.027(3) 0.039(4) 0.029(4) -0.004(3) 0.002(3) -0.001(3) C13 0.029(3) 0.081(6) 0.040(4) 0.016(4) 0.005(3) 0.001(3) C14 0.032(3) 0.059(5) 0.032(4) 0.006(3) 0.002(3) -0.003(3) C15 0.040(4) 0.069(5) 0.039(5) 0.017(4) -0.007(3) 0.007(4) C16 0.044(4) 0.130(8) 0.042(5) 0.032(5) 0.003(4) 0.009(5) C17 0.048(5) 0.146(9) 0.047(5) 0.038(6) -0.007(4) 0.009(5) C18 0.088(7) 0.120(9) 0.061(7) 0.021(6) -0.017(6) 0.032(7) C19 0.116(8) 0.080(7) 0.083(8) 0.038(6) -0.029(6) 0.001(6) C20 0.070(6) 0.071(6) 0.099(8) 0.037(6) -0.026(5) -0.005(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 O3 1.962(4) 3_666 ? Zn1 O1 2.070(4) 3_566 ? Zn1 N3 2.095(5) . ? Zn1 N1 2.120(5) . ? Zn1 O1 2.174(4) . ? O1 C1 1.281(7) . ? O1 Zn1 2.070(4) 3_566 ? O2 C1 1.217(6) . ? O3 C11 1.283(7) . ? O3 Zn1 1.962(4) 3_666 ? O4 C11 1.225(7) . ? N1 C2 1.331(7) . ? N1 N2 1.341(6) . ? N2 C4 1.358(7) . ? N2 H2 0.8600 . ? N3 C12 1.314(7) . ? N3 N4 1.353(6) . ? N4 C14 1.361(7) . ? N4 H4 0.8600 . ? C1 C2 1.492(8) . ? C2 C3 1.390(8) . ? C3 C4 1.378(8) . ? C3 H3 0.9300 . ? C4 C5 1.477(8) . ? C5 C6 1.370(9) . ? C5 C10 1.378(9) . ? C6 C7 1.386(10) . ? C6 H6 0.9300 . ? C7 C8 1.374(12) . ? C7 H7 0.9300 . ? C8 C9 1.362(12) . ? C8 H8 0.9300 . ? C9 C10 1.387(10) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.472(8) . ? C12 C13 1.399(8) . ? C13 C14 1.376(8) . ? C13 H13 0.9300 . ? C14 C15 1.476(9) . ? C15 C16 1.360(9) . ? C15 C20 1.382(10) . ? C16 C17 1.398(10) . ? C16 H16 0.9300 . ? C17 C18 1.364(12) . ? C17 H17 0.9300 . ? C18 C19 1.336(12) . ? C18 H18 0.9300 . ? C19 C20 1.385(11) . ? 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 O1 95.84(17) 3_666 3_566 ? O3 Zn1 N3 124.47(17) 3_666 . ? O1 Zn1 N3 92.41(17) 3_566 . ? O3 Zn1 N1 102.07(18) 3_666 . ? O1 Zn1 N1 144.32(17) 3_566 . ? N3 Zn1 N1 102.15(19) . . ? O3 Zn1 O1 125.07(16) 3_666 . ? O1 Zn1 O1 70.03(19) 3_566 . ? N3 Zn1 O1 109.35(17) . . ? N1 Zn1 O1 74.42(16) . . ? C1 O1 Zn1 131.2(4) . 3_566 ? C1 O1 Zn1 118.8(4) . . ? Zn1 O1 Zn1 109.97(19) 3_566 . ? C11 O3 Zn1 121.3(4) . 3_666 ? C2 N1 N2 105.1(5) . . ? C2 N1 Zn1 116.3(4) . . ? N2 N1 Zn1 137.3(4) . . ? N1 N2 C4 112.1(5) . . ? N1 N2 H2 124.0 . . ? C4 N2 H2 124.0 . . ? C12 N3 N4 106.7(5) . . ? C12 N3 Zn1 125.3(4) . . ? N4 N3 Zn1 127.4(3) . . ? N3 N4 C14 110.7(5) . . ? N3 N4 H4 124.6 . . ? C14 N4 H4 124.6 . . ? O2 C1 O1 125.5(6) . . ? O2 C1 C2 121.5(6) . . ? O1 C1 C2 113.0(5) . . ? N1 C2 C3 111.4(5) . . ? N1 C2 C1 116.9(5) . . ? C3 C2 C1 131.6(5) . . ? C4 C3 C2 105.2(5) . . ? C4 C3 H3 127.4 . . ? C2 C3 H3 127.4 . . ? N2 C4 C3 106.2(5) . . ? N2 C4 C5 123.4(5) . . ? C3 C4 C5 130.4(6) . . ? C6 C5 C10 119.3(6) . . ? C6 C5 C4 119.2(6) . . ? C10 C5 C4 121.5(6) . . ? C5 C6 C7 120.2(8) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.4(8) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 119.4(8) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.6(8) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 120.1(8) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? O4 C11 O3 124.3(5) . . ? O4 C11 C12 120.9(6) . . ? O3 C11 C12 114.6(5) . . ? N3 C12 C13 110.5(5) . . ? N3 C12 C11 120.4(5) . . ? C13 C12 C11 128.8(5) . . ? C14 C13 C12 105.7(5) . . ? C14 C13 H13 127.1 . . ? C12 C13 H13 127.1 . . ? N4 C14 C13 106.4(6) . . ? N4 C14 C15 123.1(5) . . ? C13 C14 C15 130.4(6) . . ? C16 C15 C20 119.0(7) . . ? C16 C15 C14 122.2(7) . . ? C20 C15 C14 118.7(6) . . ? C15 C16 C17 120.5(8) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.5(8) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C19 C18 C17 120.1(9) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 121.2(9) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C15 C20 C19 119.5(8) . . ? C15 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? 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 -98.5(5) 3_666 . . . ? O1 Zn1 O1 C1 178.6(6) 3_566 . . . ? N3 Zn1 O1 C1 93.2(5) . . . . ? N1 Zn1 O1 C1 -4.5(4) . . . . ? O3 Zn1 O1 Zn1 82.9(2) 3_666 . . 3_566 ? O1 Zn1 O1 Zn1 0.0 3_566 . . 3_566 ? N3 Zn1 O1 Zn1 -85.4(2) . . . 3_566 ? N1 Zn1 O1 Zn1 176.9(2) . . . 3_566 ? O3 Zn1 N1 C2 129.6(4) 3_666 . . . ? O1 Zn1 N1 C2 11.1(6) 3_566 . . . ? N3 Zn1 N1 C2 -100.8(4) . . . . ? O1 Zn1 N1 C2 6.2(4) . . . . ? O3 Zn1 N1 N2 -65.7(6) 3_666 . . . ? O1 Zn1 N1 N2 175.9(5) 3_566 . . . ? N3 Zn1 N1 N2 64.0(6) . . . . ? O1 Zn1 N1 N2 170.9(6) . . . . ? C2 N1 N2 C4 0.0(7) . . . . ? Zn1 N1 N2 C4 -165.8(5) . . . . ? O3 Zn1 N3 C12 33.9(6) 3_666 . . . ? O1 Zn1 N3 C12 132.7(5) 3_566 . . . ? N1 Zn1 N3 C12 -80.1(5) . . . . ? O1 Zn1 N3 C12 -157.6(5) . . . . ? O3 Zn1 N3 N4 -136.3(4) 3_666 . . . ? O1 Zn1 N3 N4 -37.5(5) 3_566 . . . ? N1 Zn1 N3 N4 109.7(5) . . . . ? O1 Zn1 N3 N4 32.1(5) . . . . ? C12 N3 N4 C14 0.6(7) . . . . ? Zn1 N3 N4 C14 172.3(4) . . . . ? Zn1 O1 C1 O2 2.1(10) 3_566 . . . ? Zn1 O1 C1 O2 -176.1(5) . . . . ? Zn1 O1 C1 C2 -179.6(4) 3_566 . . . ? Zn1 O1 C1 C2 2.1(7) . . . . ? N2 N1 C2 C3 1.2(7) . . . . ? Zn1 N1 C2 C3 170.5(4) . . . . ? N2 N1 C2 C1 -176.7(5) . . . . ? Zn1 N1 C2 C1 -7.4(7) . . . . ? O2 C1 C2 N1 -178.2(6) . . . . ? O1 C1 C2 N1 3.4(8) . . . . ? O2 C1 C2 C3 4.4(11) . . . . ? O1 C1 C2 C3 -173.9(7) . . . . ? N1 C2 C3 C4 -1.9(8) . . . . ? C1 C2 C3 C4 175.6(6) . . . . ? N1 N2 C4 C3 -1.2(7) . . . . ? N1 N2 C4 C5 177.9(6) . . . . ? C2 C3 C4 N2 1.8(7) . . . . ? C2 C3 C4 C5 -177.2(7) . . . . ? N2 C4 C5 C6 154.3(7) . . . . ? C3 C4 C5 C6 -26.9(12) . . . . ? N2 C4 C5 C10 -28.7(11) . . . . ? C3 C4 C5 C10 150.1(8) . . . . ? C10 C5 C6 C7 0.8(12) . . . . ? C4 C5 C6 C7 177.8(7) . . . . ? C5 C6 C7 C8 -0.1(13) . . . . ? C6 C7 C8 C9 -0.6(15) . . . . ? C7 C8 C9 C10 0.6(15) . . . . ? C6 C5 C10 C9 -0.9(12) . . . . ? C4 C5 C10 C9 -177.8(7) . . . . ? C8 C9 C10 C5 0.2(14) . . . . ? Zn1 O3 C11 O4 30.6(9) 3_666 . . . ? Zn1 O3 C11 C12 -144.4(4) 3_666 . . . ? N4 N3 C12 C13 -1.0(7) . . . . ? Zn1 N3 C12 C13 -172.9(4) . . . . ? N4 N3 C12 C11 173.0(5) . . . . ? Zn1 N3 C12 C11 1.1(8) . . . . ? O4 C11 C12 N3 -169.7(6) . . . . ? O3 C11 C12 N3 5.6(9) . . . . ? O4 C11 C12 C13 3.2(11) . . . . ? O3 C11 C12 C13 178.4(6) . . . . ? N3 C12 C13 C14 1.0(8) . . . . ? C11 C12 C13 C14 -172.4(6) . . . . ? N3 N4 C14 C13 0.0(7) . . . . ? N3 N4 C14 C15 -177.7(6) . . . . ? C12 C13 C14 N4 -0.6(8) . . . . ? C12 C13 C14 C15 176.8(7) . . . . ? N4 C14 C15 C16 -36.7(11) . . . . ? C13 C14 C15 C16 146.3(8) . . . . ? N4 C14 C15 C20 146.7(7) . . . . ? C13 C14 C15 C20 -30.3(12) . . . . ? C20 C15 C16 C17 -1.9(13) . . . . ? C14 C15 C16 C17 -178.5(7) . . . . ? C15 C16 C17 C18 -0.2(14) . . . . ? C16 C17 C18 C19 3.5(15) . . . . ? C17 C18 C19 C20 -4.8(16) . . . . ? C16 C15 C20 C19 0.8(13) . . . . ? C14 C15 C20 C19 177.4(8) . . . . ? C18 C19 C20 C15 2.6(16) . . . . ? 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 N2 H2 O2 0.86 2.02 2.765(6) 144.8 1_655 N4 H4 O4 0.86 1.82 2.673(6) 172.8 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.043 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.093 data_4 _database_code_depnum_ccdc_archive 'CCDC 799352' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N4 Ni O6' _chemical_formula_weight 469.09 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6139(7) _cell_length_b 6.9872(7) _cell_length_c 10.4414(11) _cell_angle_alpha 79.7360(10) _cell_angle_beta 82.9990(10) _cell_angle_gamma 75.0920(10) _cell_volume 457.35(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1808 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 242 _exptl_absorpt_coefficient_mu 1.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7174 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3527 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1683 _reflns_number_gt 1548 _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^)+(0.0303P)^2^+0.2683P] 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 1683 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.5000 0.0000 0.5000 0.01709(13) Uani 1 2 d S . . O1 O 0.3139(3) 0.8312(2) 0.44969(16) 0.0297(4) Uani 1 1 d . . . O2 O 0.0696(2) 0.9497(2) 0.30675(15) 0.0248(4) Uani 1 1 d . . . O3 O 0.6455(2) 0.0138(2) 0.30931(15) 0.0289(4) Uani 1 1 d . . . H1W H 0.7728 -0.0072 0.3122 0.043 Uiso 1 1 d R . . H2W H 0.6113 -0.0846 0.2742 0.043 Uiso 1 1 d R . . N1 N 0.2812(3) 0.2630(3) 0.44194(17) 0.0189(4) Uani 1 1 d . . . N2 N 0.1528(3) 0.3029(3) 0.34414(16) 0.0192(4) Uani 1 1 d . . . H2 H 0.1171 0.2125 0.3119 0.023 Uiso 1 1 calc R . . C1 C 0.2940(3) 0.4400(3) 0.4634(2) 0.0175(4) Uani 1 1 d . . . H1 H 0.3697 0.4580 0.5279 0.021 Uiso 1 1 calc R . . C2 C 0.1808(3) 0.5968(3) 0.37821(19) 0.0166(4) Uani 1 1 d . . . C3 C 0.0875(3) 0.5017(3) 0.3032(2) 0.0173(4) Uani 1 1 d . . . C4 C 0.1849(3) 0.8095(3) 0.3774(2) 0.0180(4) Uani 1 1 d . . . C5 C -0.0626(3) 0.5775(3) 0.2011(2) 0.0200(5) Uani 1 1 d . . . C6 C -0.0292(4) 0.7220(3) 0.0968(2) 0.0274(5) Uani 1 1 d . . . H6 H 0.0916 0.7693 0.0886 0.033 Uiso 1 1 calc R . . C7 C -0.1744(5) 0.7960(4) 0.0048(2) 0.0394(7) Uani 1 1 d . . . H7 H -0.1496 0.8914 -0.0656 0.047 Uiso 1 1 calc R . . C8 C -0.3545(5) 0.7300(4) 0.0164(3) 0.0436(7) Uani 1 1 d . . . H8 H -0.4536 0.7835 -0.0445 0.052 Uiso 1 1 calc R . . C9 C -0.3889(4) 0.5834(4) 0.1190(3) 0.0385(6) Uani 1 1 d . . . H9 H -0.5104 0.5372 0.1265 0.046 Uiso 1 1 calc R . . C10 C -0.2419(4) 0.5055(4) 0.2105(2) 0.0271(5) Uani 1 1 d . . . H10 H -0.2635 0.4049 0.2783 0.033 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 Ni1 0.0195(2) 0.0099(2) 0.0228(2) -0.00227(14) -0.00732(15) -0.00281(15) O1 0.0303(9) 0.0150(8) 0.0486(10) -0.0051(7) -0.0208(8) -0.0059(7) O2 0.0309(9) 0.0123(7) 0.0326(8) -0.0012(6) -0.0128(7) -0.0043(6) O3 0.0261(9) 0.0297(9) 0.0298(8) -0.0049(7) -0.0039(7) -0.0037(7) N1 0.0203(9) 0.0133(9) 0.0240(9) -0.0018(7) -0.0076(7) -0.0036(7) N2 0.0221(10) 0.0120(9) 0.0257(9) -0.0057(7) -0.0083(8) -0.0034(7) C1 0.0167(11) 0.0141(10) 0.0232(10) -0.0040(8) -0.0043(8) -0.0043(8) C2 0.0158(10) 0.0122(10) 0.0220(10) -0.0030(8) -0.0023(8) -0.0032(8) C3 0.0184(11) 0.0122(10) 0.0218(10) -0.0019(8) -0.0012(8) -0.0051(8) C4 0.0165(10) 0.0135(10) 0.0252(11) -0.0049(8) -0.0014(9) -0.0041(8) C5 0.0229(11) 0.0148(10) 0.0231(10) -0.0077(8) -0.0056(9) -0.0008(9) C6 0.0369(14) 0.0182(11) 0.0290(12) -0.0031(9) -0.0062(10) -0.0090(10) C7 0.0626(19) 0.0251(13) 0.0292(13) -0.0005(10) -0.0162(13) -0.0049(13) C8 0.0482(17) 0.0407(16) 0.0404(15) -0.0096(13) -0.0274(13) 0.0055(13) C9 0.0266(14) 0.0539(17) 0.0399(14) -0.0169(13) -0.0101(11) -0.0084(12) C10 0.0281(13) 0.0304(13) 0.0261(11) -0.0083(10) -0.0033(10) -0.0093(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.0706(17) . ? Ni1 N1 2.0706(17) 2_656 ? Ni1 O1 2.0755(14) 1_545 ? Ni1 O1 2.0755(14) 2_666 ? Ni1 O3 2.1005(15) 2_656 ? Ni1 O3 2.1005(15) . ? O1 C4 1.259(2) . ? O1 Ni1 2.0755(14) 1_565 ? O2 C4 1.257(2) . ? O3 H1W 0.8200 . ? O3 H2W 0.9213 . ? N1 C1 1.320(3) . ? N1 N2 1.353(2) . ? N2 C3 1.351(3) . ? N2 H2 0.8600 . ? C1 C2 1.395(3) . ? C1 H1 0.9300 . ? C2 C3 1.396(3) . ? C2 C4 1.492(3) . ? C3 C5 1.479(3) . ? C5 C6 1.385(3) . ? C5 C10 1.390(3) . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 C8 1.369(4) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 C10 1.387(3) . ? C9 H9 0.9300 . ? C10 H10 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 N1 Ni1 N1 180.0 . 2_656 ? N1 Ni1 O1 90.97(6) . 1_545 ? N1 Ni1 O1 89.03(6) 2_656 1_545 ? N1 Ni1 O1 89.03(6) . 2_666 ? N1 Ni1 O1 90.97(6) 2_656 2_666 ? O1 Ni1 O1 180.00(5) 1_545 2_666 ? N1 Ni1 O3 90.38(7) . 2_656 ? N1 Ni1 O3 89.62(7) 2_656 2_656 ? O1 Ni1 O3 90.93(7) 1_545 2_656 ? O1 Ni1 O3 89.07(7) 2_666 2_656 ? N1 Ni1 O3 89.62(7) . . ? N1 Ni1 O3 90.38(7) 2_656 . ? O1 Ni1 O3 89.07(7) 1_545 . ? O1 Ni1 O3 90.93(7) 2_666 . ? O3 Ni1 O3 180.0 2_656 . ? C4 O1 Ni1 150.44(14) . 1_565 ? Ni1 O3 H1W 109.4 . . ? Ni1 O3 H2W 105.6 . . ? H1W O3 H2W 111.2 . . ? C1 N1 N2 105.20(16) . . ? C1 N1 Ni1 122.98(14) . . ? N2 N1 Ni1 128.20(13) . . ? C3 N2 N1 111.82(16) . . ? C3 N2 H2 124.1 . . ? N1 N2 H2 124.1 . . ? N1 C1 C2 112.21(18) . . ? N1 C1 H1 123.9 . . ? C2 C1 H1 123.9 . . ? C1 C2 C3 104.12(17) . . ? C1 C2 C4 121.85(18) . . ? C3 C2 C4 133.97(18) . . ? N2 C3 C2 106.60(17) . . ? N2 C3 C5 120.38(18) . . ? C2 C3 C5 132.96(18) . . ? O2 C4 O1 125.04(19) . . ? O2 C4 C2 120.73(18) . . ? O1 C4 C2 114.21(17) . . ? C6 C5 C10 119.2(2) . . ? C6 C5 C3 121.1(2) . . ? C10 C5 C3 119.74(19) . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 120.1(2) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ni1 N1 C1 -76(100) 2_656 . . . ? O1 Ni1 N1 C1 171.64(17) 1_545 . . . ? O1 Ni1 N1 C1 -8.36(17) 2_666 . . . ? O3 Ni1 N1 C1 80.70(17) 2_656 . . . ? O3 Ni1 N1 C1 -99.30(17) . . . . ? N1 Ni1 N1 N2 79(100) 2_656 . . . ? O1 Ni1 N1 N2 -33.07(17) 1_545 . . . ? O1 Ni1 N1 N2 146.93(17) 2_666 . . . ? O3 Ni1 N1 N2 -124.01(17) 2_656 . . . ? O3 Ni1 N1 N2 55.99(17) . . . . ? C1 N1 N2 C3 0.8(2) . . . . ? Ni1 N1 N2 C3 -157.92(15) . . . . ? N2 N1 C1 C2 -1.9(2) . . . . ? Ni1 N1 C1 C2 158.22(14) . . . . ? N1 C1 C2 C3 2.2(2) . . . . ? N1 C1 C2 C4 -175.39(19) . . . . ? N1 N2 C3 C2 0.6(2) . . . . ? N1 N2 C3 C5 -177.01(18) . . . . ? C1 C2 C3 N2 -1.6(2) . . . . ? C4 C2 C3 N2 175.6(2) . . . . ? C1 C2 C3 C5 175.5(2) . . . . ? C4 C2 C3 C5 -7.3(4) . . . . ? Ni1 O1 C4 O2 -20.3(5) 1_565 . . . ? Ni1 O1 C4 C2 158.3(2) 1_565 . . . ? C1 C2 C4 O2 -174.6(2) . . . . ? C3 C2 C4 O2 8.6(4) . . . . ? C1 C2 C4 O1 6.8(3) . . . . ? C3 C2 C4 O1 -170.0(2) . . . . ? N2 C3 C5 C6 -133.4(2) . . . . ? C2 C3 C5 C6 49.7(3) . . . . ? N2 C3 C5 C10 47.6(3) . . . . ? C2 C3 C5 C10 -129.3(3) . . . . ? C10 C5 C6 C7 1.2(3) . . . . ? C3 C5 C6 C7 -177.8(2) . . . . ? C5 C6 C7 C8 1.0(4) . . . . ? C6 C7 C8 C9 -2.0(4) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C9 C10 C5 1.5(4) . . . . ? C6 C5 C10 C9 -2.4(3) . . . . ? C3 C5 C10 C9 176.6(2) . . . . ? 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 O3 H1W O2 0.82 1.90 2.721(2) 176.2 1_645 N2 H2 O2 0.86 1.95 2.764(2) 157.0 1_545 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.351 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.057 data_5 _database_code_depnum_ccdc_archive 'CCDC 799353' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H30 N8 Ni O4' _chemical_formula_weight 721.41 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 12.463(3) _cell_length_b 11.681(3) _cell_length_c 12.403(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.109(3) _cell_angle_gamma 90.00 _cell_volume 1765.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3106 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.23 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9286 _exptl_absorpt_correction_T_max 0.9395 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13125 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3279 _reflns_number_gt 2609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0415P)^2^+0.6962P] 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 3279 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 C14 C 0.93988(17) 0.6126(2) 0.0917(2) 0.0565(8) Uani 0.50 1 d PG A 1 C15 C 1.0354(2) 0.6003(3) 0.1726(2) 0.0848(15) Uani 0.50 1 d PG A 1 H15 H 1.0390 0.5525 0.2332 0.102 Uiso 0.50 1 calc PR A 1 C16 C 1.1280(2) 0.6662(3) 0.1562(3) 0.117(2) Uani 0.50 1 d PG A 1 H16 H 1.1940 0.6604 0.2075 0.141 Uiso 0.50 1 calc PR A 1 C17 C 1.1225(2) 0.7337(3) 0.0720(3) 0.099(2) Uani 0.50 1 d PG A 1 H17 H 1.1850 0.7734 0.0641 0.119 Uiso 0.50 1 calc PR A 1 C18 C 1.0279(2) 0.7483(2) -0.0053(3) 0.0967(18) Uani 0.50 1 d PG A 1 H18 H 1.0254 0.7989 -0.0637 0.116 Uiso 0.50 1 calc PR A 1 C19 C 0.93469(17) 0.6854(2) 0.0051(2) 0.0756(12) Uani 0.50 1 d PG A 1 H19 H 0.8696 0.6934 -0.0470 0.091 Uiso 0.50 1 calc PR A 1 C14' C 0.93568(16) 0.6156(2) 0.0668(2) 0.0565(8) Uani 0.50 1 d PG A 2 C15' C 1.03830(16) 0.6146(2) 0.1358(2) 0.0848(15) Uani 0.50 1 d PG A 2 H15' H 1.0502 0.5698 0.1991 0.102 Uiso 0.50 1 calc PR A 2 C16' C 1.12324(18) 0.6788(3) 0.1127(3) 0.117(2) Uani 0.50 1 d PG A 2 H16' H 1.1917 0.6767 0.1602 0.141 Uiso 0.50 1 calc PR A 2 C17' C 1.1077(2) 0.7462(3) 0.0195(3) 0.099(2) Uani 0.50 1 d PG A 2 H17' H 1.1652 0.7897 0.0043 0.119 Uiso 0.50 1 calc PR A 2 C18' C 1.0059(3) 0.7486(3) -0.0512(3) 0.0967(18) Uani 0.50 1 d PG A 2 H18' H 0.9949 0.7936 -0.1144 0.116 Uiso 0.50 1 calc PR A 2 C19' C 0.9206(2) 0.6839(2) -0.0277(2) 0.0756(12) Uani 0.50 1 d PG A 2 H19' H 0.8522 0.6860 -0.0755 0.091 Uiso 0.50 1 calc PR A 2 Ni1 Ni 0.5000 0.5000 0.0000 0.02779(13) Uani 1 2 d S . . O1 O 0.64878(13) 0.82817(13) 0.34795(13) 0.0394(4) Uani 1 1 d . . . O2 O 0.50774(13) 0.83547(13) 0.43302(12) 0.0393(4) Uani 1 1 d . . . N1 N 0.48791(15) 0.57982(15) 0.14728(13) 0.0329(4) Uani 1 1 d . . . N2 N 0.42163(15) 0.54527(16) 0.21452(14) 0.0328(4) Uani 1 1 d . . . H2 H 0.3772 0.4883 0.2002 0.039 Uiso 1 1 calc R . . N3 N 0.66985(15) 0.48613(16) 0.06210(14) 0.0367(4) Uani 1 1 d . . . N4 N 0.74292(15) 0.56025(17) 0.03628(16) 0.0407(5) Uani 1 1 d . A . H4 H 0.7265 0.6122 -0.0136 0.049 Uiso 1 1 calc R . . C1 C 0.54177(18) 0.66808(18) 0.19746(17) 0.0328(5) Uani 1 1 d . . . H1 H 0.5941 0.7093 0.1701 0.039 Uiso 1 1 calc R . . C2 C 0.51074(17) 0.69274(17) 0.29768(16) 0.0302(5) Uani 1 1 d . . . C3 C 0.43261(17) 0.60986(18) 0.30666(16) 0.0311(5) Uani 1 1 d . . . C4 C 0.55887(19) 0.79160(18) 0.36608(17) 0.0328(5) Uani 1 1 d . . . C5 C 0.37353(19) 0.57431(19) 0.39246(18) 0.0367(5) Uani 1 1 d . . . C6 C 0.4051(2) 0.6126(2) 0.49995(19) 0.0453(6) Uani 1 1 d . . . H6 H 0.4600 0.6674 0.5175 0.054 Uiso 1 1 calc R . . C7 C 0.3557(2) 0.5701(3) 0.5814(2) 0.0565(7) Uani 1 1 d . . . H7 H 0.3781 0.5969 0.6532 0.068 Uiso 1 1 calc R . . C8 C 0.2756(3) 0.4904(3) 0.5589(3) 0.0662(9) Uani 1 1 d . . . H8 H 0.2438 0.4616 0.6147 0.079 Uiso 1 1 calc R . . C9 C 0.2421(3) 0.4528(3) 0.4529(3) 0.0881(12) Uani 1 1 d . . . H9 H 0.1862 0.3989 0.4361 0.106 Uiso 1 1 calc R . . C10 C 0.2907(3) 0.4942(3) 0.3703(3) 0.0732(10) Uani 1 1 d . . . H10 H 0.2671 0.4676 0.2986 0.088 Uiso 1 1 calc R . . C11 C 0.7275(2) 0.4227(2) 0.1424(2) 0.0522(7) Uani 1 1 d . . . H11 H 0.6983 0.3633 0.1771 0.063 Uiso 1 1 calc R . . C12 C 0.8360(2) 0.4557(3) 0.1680(2) 0.0655(8) Uani 1 1 d . A . H12 H 0.8917 0.4246 0.2218 0.079 Uiso 1 1 calc R . . C13 C 0.8446(2) 0.5442(2) 0.0972(2) 0.0497(6) 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 C14 0.0402(15) 0.0603(19) 0.067(2) -0.0135(18) 0.0062(15) 0.0001(13) C15 0.051(2) 0.103(3) 0.091(4) 0.009(3) -0.006(2) -0.011(2) C16 0.051(2) 0.141(5) 0.146(7) -0.013(5) -0.009(3) -0.024(3) C17 0.062(3) 0.106(4) 0.125(8) -0.007(4) 0.011(4) -0.032(3) C18 0.072(3) 0.105(4) 0.113(6) 0.005(4) 0.018(4) -0.033(3) C19 0.053(2) 0.085(3) 0.086(4) 0.005(2) 0.010(2) -0.0181(19) C14' 0.0402(15) 0.0603(19) 0.067(2) -0.0135(18) 0.0062(15) 0.0001(13) C15' 0.051(2) 0.103(3) 0.091(4) 0.009(3) -0.006(2) -0.011(2) C16' 0.051(2) 0.141(5) 0.146(7) -0.013(5) -0.009(3) -0.024(3) C17' 0.062(3) 0.106(4) 0.125(8) -0.007(4) 0.011(4) -0.032(3) C18' 0.072(3) 0.105(4) 0.113(6) 0.005(4) 0.018(4) -0.033(3) C19' 0.053(2) 0.085(3) 0.086(4) 0.005(2) 0.010(2) -0.0181(19) Ni1 0.0393(2) 0.0245(2) 0.0211(2) -0.00121(15) 0.00979(15) -0.00279(16) O1 0.0465(9) 0.0334(9) 0.0415(9) -0.0061(7) 0.0161(7) -0.0020(7) O2 0.0575(10) 0.0295(8) 0.0352(9) -0.0072(7) 0.0198(7) 0.0005(7) N1 0.0447(10) 0.0313(10) 0.0256(9) -0.0027(8) 0.0137(8) -0.0024(8) N2 0.0421(10) 0.0298(9) 0.0287(9) -0.0040(8) 0.0122(8) -0.0052(8) N3 0.0423(11) 0.0387(11) 0.0302(10) 0.0021(8) 0.0099(8) 0.0015(9) N4 0.0392(11) 0.0405(12) 0.0416(11) 0.0034(9) 0.0069(9) -0.0021(9) C1 0.0438(12) 0.0286(12) 0.0281(11) -0.0008(9) 0.0123(9) -0.0026(10) C2 0.0392(12) 0.0265(11) 0.0257(10) 0.0001(9) 0.0088(9) 0.0040(9) C3 0.0416(12) 0.0285(12) 0.0247(10) -0.0007(9) 0.0104(9) 0.0061(9) C4 0.0477(13) 0.0253(11) 0.0250(11) 0.0012(9) 0.0067(10) 0.0056(10) C5 0.0457(13) 0.0344(13) 0.0337(12) 0.0035(10) 0.0167(10) 0.0066(10) C6 0.0536(15) 0.0503(15) 0.0348(13) 0.0013(11) 0.0155(11) 0.0007(12) C7 0.0687(18) 0.071(2) 0.0353(14) 0.0062(13) 0.0234(13) 0.0106(16) C8 0.083(2) 0.069(2) 0.0598(19) 0.0122(16) 0.0457(17) 0.0020(17) C9 0.108(3) 0.088(2) 0.085(3) -0.015(2) 0.059(2) -0.048(2) C10 0.089(2) 0.086(2) 0.0546(18) -0.0206(17) 0.0383(17) -0.0411(19) C11 0.0556(16) 0.0578(18) 0.0435(14) 0.0159(13) 0.0108(12) 0.0066(13) C12 0.0529(17) 0.083(2) 0.0544(17) 0.0164(16) -0.0026(14) 0.0137(16) C13 0.0392(14) 0.0551(16) 0.0520(16) -0.0066(13) 0.0031(12) 0.0023(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 C14 C19 1.3605(15) . ? C14 C15 1.3937(16) . ? C14 C13 1.444(3) . ? C15 C16 1.4368(16) . ? C15 H15 0.9300 . ? C16 C17 1.2988(14) . ? C16 H16 0.9300 . ? C17 C18 1.3647(15) . ? C17 H17 0.9300 . ? C18 C19 1.4038(16) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C14' C15' 1.3817(15) . ? C14' C19' 1.3982(16) . ? C14' C13 1.518(3) . ? C15' C16' 1.3758(15) . ? C15' H15' 0.9300 . ? C16' C17' 1.3773(15) . ? C16' H16' 0.9300 . ? C17' C18' 1.3825(15) . ? C17' H17' 0.9300 . ? C18' C19' 1.3846(15) . ? C18' H18' 0.9300 . ? C19' H19' 0.9300 . ? Ni1 N1 2.0843(17) 3_665 ? Ni1 N1 2.0844(17) . ? Ni1 N3 2.1016(19) 3_665 ? Ni1 N3 2.1016(19) . ? Ni1 O2 2.1040(15) 2_645 ? Ni1 O2 2.1040(15) 4_575 ? O1 C4 1.263(3) . ? O2 C4 1.257(3) . ? O2 Ni1 2.1040(15) 2_655 ? N1 C1 1.314(3) . ? N1 N2 1.353(2) . ? N2 C3 1.352(3) . ? N2 H2 0.8600 . ? N3 C11 1.326(3) . ? N3 N4 1.343(3) . ? N4 C13 1.345(3) . ? N4 H4 0.8600 . ? C1 C2 1.407(3) . ? C1 H1 0.9300 . ? C2 C3 1.394(3) . ? C2 C4 1.483(3) . ? C3 C5 1.475(3) . ? C5 C6 1.383(3) . ? C5 C10 1.378(4) . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 C8 1.351(4) . ? C7 H7 0.9300 . ? C8 C9 1.366(4) . ? C8 H8 0.9300 . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.376(4) . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 C14 C15 121.6 . . ? C19 C14 C13 118.62(18) . . ? C15 C14 C13 119.73(18) . . ? C14 C15 C16 115.7 . . ? C14 C15 H15 122.2 . . ? C16 C15 H15 122.2 . . ? C17 C16 C15 122.0 . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 122.2 . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C17 C18 C19 118.7 . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C14 C19 C18 119.8 . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C15' C14' C19' 117.9 . . ? C15' C14' C13 119.01(17) . . ? C19' C14' C13 123.05(17) . . ? C16' C15' C14' 121.3 . . ? C16' C15' H15' 119.4 . . ? C14' C15' H15' 119.4 . . ? C15' C16' C17' 120.5 . . ? C15' C16' H16' 119.8 . . ? C17' C16' H16' 119.8 . . ? C16' C17' C18' 119.5 . . ? C16' C17' H17' 120.2 . . ? C18' C17' H17' 120.2 . . ? C17' C18' C19' 119.9 . . ? C17' C18' H18' 120.0 . . ? C19' C18' H18' 120.0 . . ? C18' C19' C14' 120.9 . . ? C18' C19' H19' 119.6 . . ? C14' C19' H19' 119.6 . . ? N1 Ni1 N1 180.0 3_665 . ? N1 Ni1 N3 88.03(7) 3_665 3_665 ? N1 Ni1 N3 91.97(7) . 3_665 ? N1 Ni1 N3 91.96(7) 3_665 . ? N1 Ni1 N3 88.03(7) . . ? N3 Ni1 N3 180.0 3_665 . ? N1 Ni1 O2 87.43(6) 3_665 2_645 ? N1 Ni1 O2 92.57(6) . 2_645 ? N3 Ni1 O2 95.11(7) 3_665 2_645 ? N3 Ni1 O2 84.89(7) . 2_645 ? N1 Ni1 O2 92.57(6) 3_665 4_575 ? N1 Ni1 O2 87.43(6) . 4_575 ? N3 Ni1 O2 84.89(7) 3_665 4_575 ? N3 Ni1 O2 95.11(7) . 4_575 ? O2 Ni1 O2 180.00(8) 2_645 4_575 ? C4 O2 Ni1 134.81(14) . 2_655 ? C1 N1 N2 105.04(16) . . ? C1 N1 Ni1 129.98(15) . . ? N2 N1 Ni1 124.94(13) . . ? C3 N2 N1 112.83(18) . . ? C3 N2 H2 123.6 . . ? N1 N2 H2 123.6 . . ? C11 N3 N4 104.61(19) . . ? C11 N3 Ni1 131.58(17) . . ? N4 N3 Ni1 122.97(14) . . ? N3 N4 C13 112.5(2) . . ? N3 N4 H4 123.8 . . ? C13 N4 H4 123.8 . . ? N1 C1 C2 111.80(19) . . ? N1 C1 H1 124.1 . . ? C2 C1 H1 124.1 . . ? C3 C2 C1 104.74(18) . . ? C3 C2 C4 134.47(19) . . ? C1 C2 C4 120.78(19) . . ? N2 C3 C2 105.58(18) . . ? N2 C3 C5 118.4(2) . . ? C2 C3 C5 135.7(2) . . ? O2 C4 O1 124.9(2) . . ? O2 C4 C2 119.7(2) . . ? O1 C4 C2 115.41(19) . . ? C6 C5 C10 117.5(2) . . ? C6 C5 C3 121.4(2) . . ? C10 C5 C3 120.9(2) . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 121.4(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C9 121.1(3) . . ? C5 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? N3 C11 C12 111.6(2) . . ? N3 C11 H11 124.2 . . ? C12 C11 H11 124.2 . . ? C11 C12 C13 105.5(2) . . ? C11 C12 H12 127.2 . . ? C13 C12 H12 127.2 . . ? N4 C13 C12 105.8(2) . . ? N4 C13 C14 125.7(2) . . ? C12 C13 C14 128.4(2) . . ? N4 C13 C14' 116.7(2) . . ? C12 C13 C14' 137.2(2) . . ? C14 C13 C14' 11.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 C14 C15 C16 -2.0 . . . . ? C13 C14 C15 C16 176.0(2) . . . . ? C14 C15 C16 C17 0.7 . . . . ? C15 C16 C17 C18 1.3 . . . . ? C16 C17 C18 C19 -2.0 . . . . ? C15 C14 C19 C18 1.4 . . . . ? C13 C14 C19 C18 -176.6(2) . . . . ? C17 C18 C19 C14 0.6 . . . . ? C19' C14' C15' C16' 0.0 . . . . ? C13 C14' C15' C16' -179.2(2) . . . . ? C14' C15' C16' C17' 0.1 . . . . ? C15' C16' C17' C18' -0.3 . . . . ? C16' C17' C18' C19' 0.3 . . . . ? C17' C18' C19' C14' -0.1 . . . . ? C15' C14' C19' C18' 0.0 . . . . ? C13 C14' C19' C18' 179.2(2) . . . . ? N1 Ni1 N1 C1 21(6) 3_665 . . . ? N3 Ni1 N1 C1 -127.52(19) 3_665 . . . ? N3 Ni1 N1 C1 52.48(19) . . . . ? O2 Ni1 N1 C1 137.27(19) 2_645 . . . ? O2 Ni1 N1 C1 -42.73(19) 4_575 . . . ? N1 Ni1 N1 N2 -157(6) 3_665 . . . ? N3 Ni1 N1 N2 55.07(17) 3_665 . . . ? N3 Ni1 N1 N2 -124.93(17) . . . . ? O2 Ni1 N1 N2 -40.14(17) 2_645 . . . ? O2 Ni1 N1 N2 139.86(17) 4_575 . . . ? C1 N1 N2 C3 -0.2(2) . . . . ? Ni1 N1 N2 C3 177.80(14) . . . . ? N1 Ni1 N3 C11 -110.2(2) 3_665 . . . ? N1 Ni1 N3 C11 69.8(2) . . . . ? N3 Ni1 N3 C11 -143.3(13) 3_665 . . . ? O2 Ni1 N3 C11 -23.0(2) 2_645 . . . ? O2 Ni1 N3 C11 157.0(2) 4_575 . . . ? N1 Ni1 N3 N4 82.01(17) 3_665 . . . ? N1 Ni1 N3 N4 -97.99(17) . . . . ? N3 Ni1 N3 N4 49.0(13) 3_665 . . . ? O2 Ni1 N3 N4 169.25(17) 2_645 . . . ? O2 Ni1 N3 N4 -10.75(17) 4_575 . . . ? C11 N3 N4 C13 0.7(3) . . . . ? Ni1 N3 N4 C13 171.23(16) . . . . ? N2 N1 C1 C2 -0.4(2) . . . . ? Ni1 N1 C1 C2 -178.23(14) . . . . ? N1 C1 C2 C3 0.8(2) . . . . ? N1 C1 C2 C4 -178.00(18) . . . . ? N1 N2 C3 C2 0.6(2) . . . . ? N1 N2 C3 C5 -173.81(18) . . . . ? C1 C2 C3 N2 -0.8(2) . . . . ? C4 C2 C3 N2 177.7(2) . . . . ? C1 C2 C3 C5 172.2(2) . . . . ? C4 C2 C3 C5 -9.3(4) . . . . ? Ni1 O2 C4 O1 25.5(3) 2_655 . . . ? Ni1 O2 C4 C2 -151.49(15) 2_655 . . . ? C3 C2 C4 O2 -21.8(4) . . . . ? C1 C2 C4 O2 156.6(2) . . . . ? C3 C2 C4 O1 161.0(2) . . . . ? C1 C2 C4 O1 -20.6(3) . . . . ? N2 C3 C5 C6 160.0(2) . . . . ? C2 C3 C5 C6 -12.4(4) . . . . ? N2 C3 C5 C10 -14.5(3) . . . . ? C2 C3 C5 C10 173.1(3) . . . . ? C10 C5 C6 C7 0.9(4) . . . . ? C3 C5 C6 C7 -173.8(2) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C6 C7 C8 C9 -1.0(5) . . . . ? C7 C8 C9 C10 1.1(6) . . . . ? C6 C5 C10 C9 -0.8(5) . . . . ? C3 C5 C10 C9 173.9(3) . . . . ? C8 C9 C10 C5 -0.2(6) . . . . ? N4 N3 C11 C12 0.1(3) . . . . ? Ni1 N3 C11 C12 -169.31(19) . . . . ? N3 C11 C12 C13 -0.8(4) . . . . ? N3 N4 C13 C12 -1.1(3) . . . . ? N3 N4 C13 C14 -177.6(2) . . . . ? N3 N4 C13 C14' 174.0(2) . . . . ? C11 C12 C13 N4 1.1(3) . . . . ? C11 C12 C13 C14 177.5(3) . . . . ? C11 C12 C13 C14' -172.5(3) . . . . ? C19 C14 C13 N4 -13.6(4) . . . . ? C15 C14 C13 N4 168.4(2) . . . . ? C19 C14 C13 C12 170.7(3) . . . . ? C15 C14 C13 C12 -7.3(4) . . . . ? C19 C14 C13 C14' 27.05(9) . . . . ? C15 C14 C13 C14' -150.95(15) . . . . ? C15' C14' C13 N4 170.92(19) . . . . ? C19' C14' C13 N4 -8.3(3) . . . . ? C15' C14' C13 C12 -15.9(5) . . . . ? C19' C14' C13 C12 164.8(3) . . . . ? C15' C14' C13 C14 27.23(18) . . . . ? C19' C14' C13 C14 -152.01(7) . . . . ? 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 N4 H4 O1 0.86 1.92 2.717(2) 154.2 4_575 N2 H2 O1 0.86 1.97 2.742(2) 148.8 2_645 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.282 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.057 data_6 _database_code_depnum_ccdc_archive 'CCDC 799354' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Cu N4 O6' _chemical_formula_weight 473.92 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 7.4920(8) _cell_length_b 10.6557(12) _cell_length_c 12.1671(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.4420(10) _cell_angle_gamma 90.00 _cell_volume 955.24(18) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 486 _exptl_absorpt_coefficient_mu 1.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7147 _exptl_absorpt_correction_T_max 0.8248 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 6655 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1754 _reflns_number_gt 1633 _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^)+(0.0354P)^2^+0.5003P] 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 1754 _refine_ls_number_parameters 150 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.01652(11) Uani 1 2 d S . . O1 O 0.60419(17) 0.67742(13) 0.38443(10) 0.0330(3) Uani 1 1 d . . . O2 O 0.34562(15) 0.57154(10) 0.36392(9) 0.0208(2) Uani 1 1 d . . . O3 O 0.9674(2) 0.61389(19) 0.39732(13) 0.0533(4) Uani 1 1 d D . . N1 N 0.23806(18) 0.81306(13) 0.07142(11) 0.0220(3) Uani 1 1 d . . . H1 H 0.1564 0.8287 0.0137 0.026 Uiso 1 1 calc R . . N2 N 0.39723(19) 0.87667(12) 0.09760(11) 0.0214(3) Uani 1 1 d . . . C1 C 0.4493(2) 0.65405(14) 0.33112(13) 0.0197(3) Uani 1 1 d . . . C2 C 0.3836(2) 0.72637(15) 0.22680(13) 0.0196(3) Uani 1 1 d . . . C3 C 0.2231(2) 0.72211(14) 0.14691(12) 0.0195(3) Uani 1 1 d . . . C4 C 0.4844(2) 0.82428(15) 0.19120(13) 0.0215(3) Uani 1 1 d . . . H4 H 0.5983 0.8495 0.2285 0.026 Uiso 1 1 calc R . . C5 C 0.0589(2) 0.64195(15) 0.13333(13) 0.0213(3) Uani 1 1 d . . . C6 C -0.1135(2) 0.69302(17) 0.09926(14) 0.0284(4) Uani 1 1 d . . . H6 H -0.1267 0.7789 0.0865 0.034 Uiso 1 1 calc R . . C7 C -0.2659(3) 0.6160(2) 0.08425(16) 0.0357(4) Uani 1 1 d . . . H7 H -0.3803 0.6503 0.0597 0.043 Uiso 1 1 calc R . . C8 C -0.2483(3) 0.48864(19) 0.10565(18) 0.0381(5) Uani 1 1 d . . . H8 H -0.3510 0.4380 0.0978 0.046 Uiso 1 1 calc R . . C9 C -0.0775(3) 0.43654(18) 0.13886(15) 0.0361(5) Uani 1 1 d . . . H9 H -0.0655 0.3509 0.1528 0.043 Uiso 1 1 calc R . . C10 C 0.0759(3) 0.51226(15) 0.15133(15) 0.0280(4) Uani 1 1 d . . . H10 H 0.1905 0.4767 0.1717 0.034 Uiso 1 1 calc R . . H1W H 0.8598(17) 0.633(2) 0.385(2) 0.065(9) Uiso 1 1 d D . . H2W H 0.999(3) 0.578(2) 0.3439(16) 0.067(9) 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 Cu1 0.02208(17) 0.01537(16) 0.01126(16) 0.00044(9) 0.00073(10) 0.00279(9) O1 0.0270(7) 0.0395(7) 0.0280(7) 0.0076(6) -0.0073(5) -0.0054(6) O2 0.0242(6) 0.0218(6) 0.0157(5) 0.0038(4) 0.0014(4) 0.0019(4) O3 0.0292(8) 0.0930(13) 0.0354(8) -0.0249(8) 0.0000(6) -0.0012(8) N1 0.0241(7) 0.0228(7) 0.0168(6) 0.0043(5) -0.0023(5) -0.0035(5) N2 0.0252(7) 0.0204(7) 0.0173(7) 0.0014(5) 0.0004(5) -0.0052(6) C1 0.0231(8) 0.0192(8) 0.0160(7) -0.0005(6) 0.0013(6) 0.0032(6) C2 0.0220(8) 0.0198(8) 0.0166(7) 0.0008(6) 0.0023(6) 0.0001(6) C3 0.0227(8) 0.0191(7) 0.0164(7) 0.0013(6) 0.0027(6) 0.0006(6) C4 0.0237(8) 0.0227(8) 0.0169(7) 0.0005(6) -0.0001(6) -0.0028(6) C5 0.0246(9) 0.0242(8) 0.0146(7) 0.0015(6) 0.0020(6) -0.0033(7) C6 0.0282(9) 0.0280(9) 0.0287(9) 0.0012(7) 0.0047(7) 0.0001(7) C7 0.0239(9) 0.0476(11) 0.0358(10) -0.0042(9) 0.0059(7) -0.0033(8) C8 0.0363(12) 0.0442(12) 0.0343(11) -0.0032(8) 0.0076(9) -0.0193(9) C9 0.0521(12) 0.0263(9) 0.0279(9) 0.0025(8) 0.0022(8) -0.0127(9) C10 0.0330(10) 0.0252(9) 0.0230(9) 0.0035(7) -0.0021(7) -0.0014(7) _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 Cu1 O2 1.9915(10) . ? Cu1 O2 1.9916(10) 3_666 ? Cu1 N2 2.0152(13) 2_645 ? Cu1 N2 2.0153(13) 4_576 ? Cu1 O1 2.5610(14) . ? O1 C1 1.247(2) . ? O2 C1 1.284(2) . ? O3 H1W 0.820(9) . ? O3 H2W 0.822(9) . ? N1 C3 1.354(2) . ? N1 N2 1.3584(19) . ? N1 H1 0.8600 . ? N2 C4 1.329(2) . ? N2 Cu1 2.0153(13) 2_655 ? C1 C2 1.490(2) . ? C2 C4 1.402(2) . ? C2 C3 1.403(2) . ? C3 C5 1.482(2) . ? C4 H4 0.9300 . ? C5 C6 1.393(2) . ? C5 C10 1.401(2) . ? C6 C7 1.391(3) . ? C6 H6 0.9300 . ? C7 C8 1.384(3) . ? C7 H7 0.9300 . ? C8 C9 1.387(3) . ? C8 H8 0.9300 . ? C9 C10 1.390(3) . ? C9 H9 0.9300 . ? C10 H10 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 O2 Cu1 O2 180.0 . 3_666 ? O2 Cu1 N2 89.20(5) . 2_645 ? O2 Cu1 N2 90.80(5) 3_666 2_645 ? O2 Cu1 N2 90.80(5) . 4_576 ? O2 Cu1 N2 89.20(5) 3_666 4_576 ? N2 Cu1 N2 180.00(6) 2_645 4_576 ? C1 O2 Cu1 103.15(9) . . ? H1W O3 H2W 112.5(16) . . ? C3 N1 N2 112.05(13) . . ? C3 N1 H1 124.0 . . ? N2 N1 H1 124.0 . . ? C4 N2 N1 105.40(13) . . ? C4 N2 Cu1 126.73(11) . 2_655 ? N1 N2 Cu1 126.88(10) . 2_655 ? O1 C1 O2 122.24(14) . . ? O1 C1 C2 118.18(14) . . ? O2 C1 C2 119.58(14) . . ? C4 C2 C3 104.61(14) . . ? C4 C2 C1 122.31(14) . . ? C3 C2 C1 133.05(14) . . ? N1 C3 C2 106.30(14) . . ? N1 C3 C5 120.41(14) . . ? C2 C3 C5 133.29(14) . . ? N2 C4 C2 111.64(14) . . ? N2 C4 H4 124.2 . . ? C2 C4 H4 124.2 . . ? C6 C5 C10 119.01(16) . . ? C6 C5 C3 120.92(15) . . ? C10 C5 C3 120.04(15) . . ? C7 C6 C5 120.22(17) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.38(19) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.94(18) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 120.05(18) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 120.36(18) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? 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 O2 Cu1 O2 C1 62(17) 3_666 . . . ? N2 Cu1 O2 C1 -87.01(10) 2_645 . . . ? N2 Cu1 O2 C1 92.99(10) 4_576 . . . ? C3 N1 N2 C4 0.26(18) . . . . ? C3 N1 N2 Cu1 169.43(11) . . . 2_655 ? Cu1 O2 C1 O1 -3.07(18) . . . . ? Cu1 O2 C1 C2 177.76(11) . . . . ? O1 C1 C2 C4 -4.3(2) . . . . ? O2 C1 C2 C4 174.95(14) . . . . ? O1 C1 C2 C3 178.01(17) . . . . ? O2 C1 C2 C3 -2.8(3) . . . . ? N2 N1 C3 C2 -0.47(18) . . . . ? N2 N1 C3 C5 179.97(13) . . . . ? C4 C2 C3 N1 0.47(17) . . . . ? C1 C2 C3 N1 178.50(16) . . . . ? C4 C2 C3 C5 179.95(17) . . . . ? C1 C2 C3 C5 -2.0(3) . . . . ? N1 N2 C4 C2 0.06(18) . . . . ? Cu1 N2 C4 C2 -169.13(11) 2_655 . . . ? C3 C2 C4 N2 -0.34(18) . . . . ? C1 C2 C4 N2 -178.63(14) . . . . ? N1 C3 C5 C6 -41.4(2) . . . . ? C2 C3 C5 C6 139.20(18) . . . . ? N1 C3 C5 C10 136.56(17) . . . . ? C2 C3 C5 C10 -42.8(3) . . . . ? C10 C5 C6 C7 0.4(3) . . . . ? C3 C5 C6 C7 178.42(15) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? C6 C7 C8 C9 -2.0(3) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C5 1.7(3) . . . . ? C6 C5 C10 C9 -2.1(3) . . . . ? C3 C5 C10 C9 179.93(16) . . . . ? 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 O3 H2W O2 0.822(9) 2.57(2) 2.969(2) 111.5(19) 1_655 O3 H1W O1 0.820(9) 1.970(10) 2.781(2) 170(2) . N1 H1 O3 0.86 1.91 2.765(2) 171.2 4_475 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.303 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.051 data_7 _database_code_depnum_ccdc_archive 'CCDC 799355' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N4 O4 Zn' _chemical_formula_weight 439.72 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 Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 16.5749(19) _cell_length_b 18.395(2) _cell_length_c 22.912(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6985.8(14) _cell_formula_units_Z 16 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6046 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3584 _exptl_absorpt_coefficient_mu 1.445 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6091 _exptl_absorpt_correction_T_max 0.7493 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14743 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2009 _reflns_number_gt 1815 _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^)+(0.0410P)^2^+32.5803P] 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 2009 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.6250 1.1250 0.275596(14) 0.02202(12) Uani 1 2 d S . . O1 O 0.43028(13) 1.03722(9) 0.07621(8) 0.0440(5) Uani 1 1 d . . . O2 O 0.45376(11) 0.91801(9) 0.07745(8) 0.0370(4) Uani 1 1 d . . . N1 N 0.57312(12) 1.04898(10) 0.22462(8) 0.0269(4) Uani 1 1 d . . . N2 N 0.58681(12) 0.97626(10) 0.22926(8) 0.0265(4) Uani 1 1 d . . . H2 H 0.6167 0.9568 0.2557 0.032 Uiso 1 1 calc R . . C1 C 0.52446(15) 1.05707(12) 0.17895(10) 0.0279(5) Uani 1 1 d . . . H1 H 0.5045 1.1015 0.1660 0.034 Uiso 1 1 calc R . . C2 C 0.50729(13) 0.98990(12) 0.15299(9) 0.0244(4) Uani 1 1 d . . . C3 C 0.54783(13) 0.93854(12) 0.18741(10) 0.0252(4) Uani 1 1 d . . . C4 C 0.45973(13) 0.98185(12) 0.09817(9) 0.0249(4) Uani 1 1 d . . . C5 C 0.55222(15) 0.85809(13) 0.18673(11) 0.0315(5) Uani 1 1 d . . . C6 C 0.48489(17) 0.81617(14) 0.17329(13) 0.0416(6) Uani 1 1 d . . . H6 H 0.4362 0.8387 0.1643 0.050 Uiso 1 1 calc R . . C7 C 0.4899(2) 0.74107(16) 0.17323(15) 0.0547(8) Uani 1 1 d . . . H7 H 0.4450 0.7134 0.1634 0.066 Uiso 1 1 calc R . . C8 C 0.5610(2) 0.70746(16) 0.18767(17) 0.0592(9) Uani 1 1 d . . . H8 H 0.5639 0.6570 0.1880 0.071 Uiso 1 1 calc R . . C9 C 0.6283(2) 0.74812(16) 0.20175(16) 0.0539(8) Uani 1 1 d . . . H9 H 0.6762 0.7250 0.2117 0.065 Uiso 1 1 calc R . . C10 C 0.62441(17) 0.82349(14) 0.20111(13) 0.0386(6) Uani 1 1 d . . . H10 H 0.6699 0.8509 0.2102 0.046 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 0.0298(2) 0.01869(18) 0.01758(18) 0.000 0.000 -0.00028(14) O1 0.0645(13) 0.0279(9) 0.0397(10) 0.0009(8) -0.0309(10) -0.0005(9) O2 0.0464(10) 0.0275(9) 0.0370(9) -0.0105(7) -0.0168(8) 0.0048(8) N1 0.0383(11) 0.0196(9) 0.0227(9) -0.0031(7) -0.0078(8) 0.0018(8) N2 0.0332(10) 0.0218(9) 0.0244(9) -0.0005(7) -0.0088(8) 0.0028(8) C1 0.0382(12) 0.0217(10) 0.0239(10) -0.0015(8) -0.0087(9) 0.0031(9) C2 0.0295(11) 0.0219(10) 0.0219(10) -0.0022(8) -0.0052(9) 0.0014(8) C3 0.0277(11) 0.0228(10) 0.0252(10) -0.0027(8) -0.0030(9) 0.0006(8) C4 0.0258(10) 0.0263(11) 0.0227(10) -0.0021(8) -0.0035(9) -0.0023(8) C5 0.0366(12) 0.0233(11) 0.0348(12) -0.0011(9) -0.0089(10) 0.0017(9) C6 0.0416(15) 0.0303(13) 0.0527(16) 0.0026(11) -0.0135(13) -0.0022(11) C7 0.0588(19) 0.0334(14) 0.072(2) 0.0003(14) -0.0190(17) -0.0096(13) C8 0.072(2) 0.0245(14) 0.081(2) -0.0016(14) -0.0178(19) 0.0045(14) C9 0.0579(19) 0.0334(15) 0.071(2) -0.0001(14) -0.0158(17) 0.0144(13) C10 0.0386(13) 0.0299(12) 0.0474(15) -0.0020(11) -0.0106(12) 0.0030(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.9344(17) 19_676 ? Zn1 O2 1.9344(17) 20_666 ? Zn1 N1 2.0148(18) . ? Zn1 N1 2.0149(18) 14_565 ? O1 C4 1.236(3) . ? O2 C4 1.271(3) . ? O2 Zn1 1.9344(17) 27_575 ? N1 C1 1.329(3) . ? N1 N2 1.361(3) . ? N2 C3 1.348(3) . ? N2 H2 0.8600 . ? C1 C2 1.401(3) . ? C1 H1 0.9300 . ? C2 C3 1.402(3) . ? C2 C4 1.490(3) . ? C3 C5 1.482(3) . ? C5 C6 1.391(4) . ? C5 C10 1.395(3) . ? C6 C7 1.384(4) . ? C6 H6 0.9300 . ? C7 C8 1.372(5) . ? C7 H7 0.9300 . ? C8 C9 1.381(5) . ? C8 H8 0.9300 . ? C9 C10 1.388(4) . ? C9 H9 0.9300 . ? C10 H10 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 O2 Zn1 O2 104.21(12) 19_676 20_666 ? O2 Zn1 N1 111.12(7) 19_676 . ? O2 Zn1 N1 110.60(8) 20_666 . ? O2 Zn1 N1 110.60(8) 19_676 14_565 ? O2 Zn1 N1 111.11(7) 20_666 14_565 ? N1 Zn1 N1 109.14(11) . 14_565 ? C4 O2 Zn1 131.30(16) . 27_575 ? C1 N1 N2 105.83(17) . . ? C1 N1 Zn1 129.60(15) . . ? N2 N1 Zn1 124.45(14) . . ? C3 N2 N1 111.74(18) . . ? C3 N2 H2 124.1 . . ? N1 N2 H2 124.1 . . ? N1 C1 C2 111.0(2) . . ? N1 C1 H1 124.5 . . ? C2 C1 H1 124.5 . . ? C1 C2 C3 104.97(19) . . ? C1 C2 C4 123.6(2) . . ? C3 C2 C4 131.3(2) . . ? N2 C3 C2 106.42(19) . . ? N2 C3 C5 119.9(2) . . ? C2 C3 C5 133.7(2) . . ? O1 C4 O2 125.4(2) . . ? O1 C4 C2 118.0(2) . . ? O2 C4 C2 116.6(2) . . ? C6 C5 C10 119.2(2) . . ? C6 C5 C3 121.1(2) . . ? C10 C5 C3 119.7(2) . . ? C7 C6 C5 120.4(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 119.8(3) . . ? C9 C10 H10 120.1 . . ? C5 C10 H10 120.1 . . ? 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 O2 Zn1 N1 C1 -170.5(2) 19_676 . . . ? O2 Zn1 N1 C1 74.2(2) 20_666 . . . ? N1 Zn1 N1 C1 -48.3(2) 14_565 . . . ? O2 Zn1 N1 N2 5.0(2) 19_676 . . . ? O2 Zn1 N1 N2 -110.28(19) 20_666 . . . ? N1 Zn1 N1 N2 127.2(2) 14_565 . . . ? C1 N1 N2 C3 0.1(3) . . . . ? Zn1 N1 N2 C3 -176.34(16) . . . . ? N2 N1 C1 C2 -1.0(3) . . . . ? Zn1 N1 C1 C2 175.14(17) . . . . ? N1 C1 C2 C3 1.5(3) . . . . ? N1 C1 C2 C4 -175.0(2) . . . . ? N1 N2 C3 C2 0.9(3) . . . . ? N1 N2 C3 C5 -177.2(2) . . . . ? C1 C2 C3 N2 -1.4(3) . . . . ? C4 C2 C3 N2 174.7(2) . . . . ? C1 C2 C3 C5 176.3(3) . . . . ? C4 C2 C3 C5 -7.5(4) . . . . ? Zn1 O2 C4 O1 -23.6(4) 27_575 . . . ? Zn1 O2 C4 C2 157.30(17) 27_575 . . . ? C1 C2 C4 O1 -4.0(4) . . . . ? C3 C2 C4 O1 -179.5(2) . . . . ? C1 C2 C4 O2 175.2(2) . . . . ? C3 C2 C4 O2 -0.3(4) . . . . ? N2 C3 C5 C6 140.1(3) . . . . ? C2 C3 C5 C6 -37.4(4) . . . . ? N2 C3 C5 C10 -38.3(4) . . . . ? C2 C3 C5 C10 144.2(3) . . . . ? C10 C5 C6 C7 -1.1(5) . . . . ? C3 C5 C6 C7 -179.6(3) . . . . ? C5 C6 C7 C8 1.4(5) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C5 0.6(5) . . . . ? C6 C5 C10 C9 0.1(4) . . . . ? C3 C5 C10 C9 178.6(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 N2 H2 O1 0.86 1.93 2.720(3) 151.4 19_676 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.471 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.069 data_8 _database_code_depnum_ccdc_archive 'CCDC 799356' #TrackingRef '- revised crystal data and checkCIF of complexes 1-8-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 N6 O6 Zn2' _chemical_formula_weight 691.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 14.377(4) _cell_length_b 13.872(3) _cell_length_c 14.606(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.988(3) _cell_angle_gamma 90.00 _cell_volume 2838.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4433 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5785 _exptl_absorpt_correction_T_max 0.7859 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24474 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6509 _reflns_number_gt 3889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0573P)^2^+3.6690P] 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 6509 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1057 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.83735(3) 0.82606(4) 0.27054(3) 0.02513(15) Uani 1 1 d . . . Zn2 Zn 0.58936(3) 0.83010(4) 0.21253(3) 0.02363(15) Uani 1 1 d . . . O1 O 0.9442(3) 1.2424(3) 0.2548(4) 0.0747(15) Uani 1 1 d . . . O2 O 1.0765(2) 1.2131(3) 0.2093(3) 0.0421(9) Uani 1 1 d . . . O3 O 0.6494(2) 0.7266(3) -0.1652(2) 0.0391(9) Uani 1 1 d . . . O4 O 0.7994(2) 0.6853(3) -0.1105(2) 0.0409(9) Uani 1 1 d . . . O5 O 0.2975(2) 0.4755(2) 0.2323(2) 0.0375(8) Uani 1 1 d . . . O6 O 0.4550(2) 0.4592(2) 0.2704(3) 0.0399(9) Uani 1 1 d . . . N1 N 0.9181(3) 0.9402(3) 0.2581(3) 0.0309(9) Uani 1 1 d . . . N2 N 1.0019(3) 0.9259(3) 0.2299(3) 0.0380(10) Uani 1 1 d . . . H2 H 1.0254 0.8700 0.2233 0.046 Uiso 1 1 calc R . . N3 N 0.7608(3) 0.7892(3) 0.1441(3) 0.0334(9) Uani 1 1 d . . . N4 N 0.6604(3) 0.7991(3) 0.1166(3) 0.0296(9) Uani 1 1 d . . . N5 N 0.4757(3) 0.7402(3) 0.1910(3) 0.0308(9) Uani 1 1 d . . . N6 N 0.3859(3) 0.7465(3) 0.1382(3) 0.0312(9) Uani 1 1 d . . . H3 H 0.3636 0.7968 0.1064 0.037 Uiso 1 1 calc R . . C1 C 0.9080(4) 1.0359(4) 0.2578(4) 0.0422(13) Uani 1 1 d . . . H1 H 0.8567 1.0679 0.2730 0.051 Uiso 1 1 calc R . . C2 C 0.9851(3) 1.0818(4) 0.2315(3) 0.0336(12) Uani 1 1 d . . . C3 C 1.0009(4) 1.1890(4) 0.2326(4) 0.0385(13) Uani 1 1 d . . . C4 C 1.0427(3) 1.0084(4) 0.2140(4) 0.0386(12) Uani 1 1 d . . . C5 C 1.1354(4) 1.0084(4) 0.1829(4) 0.0427(13) Uani 1 1 d . . . C6 C 1.1376(4) 1.0289(5) 0.0914(5) 0.0610(17) Uani 1 1 d . . . H6 H 1.0816 1.0460 0.0490 0.073 Uiso 1 1 calc R . . C7 C 1.2230(5) 1.0243(5) 0.0616(5) 0.0661(19) Uani 1 1 d . . . H7 H 1.2233 1.0351 -0.0011 0.079 Uiso 1 1 calc R . . C8 C 1.3059(4) 1.0040(4) 0.1243(5) 0.0598(18) Uani 1 1 d . . . H8 H 1.3631 1.0019 0.1048 0.072 Uiso 1 1 calc R . . C9 C 1.3045(4) 0.9870(6) 0.2136(6) 0.078(2) Uani 1 1 d . . . H9 H 1.3614 0.9736 0.2564 0.093 Uiso 1 1 calc R . . C10 C 1.2193(4) 0.9891(6) 0.2444(5) 0.077(2) Uani 1 1 d . . . H10 H 1.2200 0.9771 0.3072 0.092 Uiso 1 1 calc R . . C11 C 0.7895(4) 0.7533(4) 0.0729(3) 0.0374(12) Uani 1 1 d . . . H11 H 0.8525 0.7370 0.0738 0.045 Uiso 1 1 calc R . . C12 C 0.7129(3) 0.7424(3) -0.0056(3) 0.0265(10) Uani 1 1 d . . . C13 C 0.7215(4) 0.7147(4) -0.1011(3) 0.0328(11) Uani 1 1 d . . . C14 C 0.6334(3) 0.7715(4) 0.0268(3) 0.0336(11) Uani 1 1 d . . . C15 C 0.4825(4) 0.8613(5) -0.0244(4) 0.0532(16) Uani 1 1 d . . . H15 H 0.5151 0.9167 0.0005 0.064 Uiso 1 1 calc R . . C16 C 0.3867(5) 0.8669(6) -0.0644(4) 0.0636(19) Uani 1 1 d . . . H16 H 0.3556 0.9260 -0.0665 0.076 Uiso 1 1 calc R . . C17 C 0.3369(5) 0.7878(8) -0.1008(4) 0.078(2) Uani 1 1 d . . . H17 H 0.2718 0.7924 -0.1268 0.094 Uiso 1 1 calc R . . C18 C 0.3823(5) 0.7012(7) -0.0993(5) 0.081(2) Uani 1 1 d . . . H18 H 0.3483 0.6464 -0.1239 0.097 Uiso 1 1 calc R . . C19 C 0.4811(4) 0.6953(5) -0.0604(5) 0.0615(18) Uani 1 1 d . . . H19 H 0.5131 0.6372 -0.0614 0.074 Uiso 1 1 calc R . . C20 C 0.5307(3) 0.7763(4) -0.0205(3) 0.0384(12) Uani 1 1 d . . . C21 C 0.4806(3) 0.6533(3) 0.2281(3) 0.0336(12) Uani 1 1 d . . . H21 H 0.5349 0.6285 0.2682 0.040 Uiso 1 1 calc R . . C22 C 0.3955(3) 0.6029(3) 0.2006(3) 0.0284(10) Uani 1 1 d . . . C23 C 0.3786(3) 0.5069(3) 0.2364(3) 0.0301(11) Uani 1 1 d . . . C24 C 0.3348(3) 0.6656(4) 0.1407(3) 0.0307(10) Uani 1 1 d . . . C25 C 0.2363(3) 0.6573(4) 0.0855(3) 0.0366(12) Uani 1 1 d . . . C26 C 0.2049(4) 0.5725(5) 0.0401(4) 0.0516(15) Uani 1 1 d . . . H26 H 0.2459 0.5199 0.0449 0.062 Uiso 1 1 calc R . . C27 C 0.1116(5) 0.5656(6) -0.0132(5) 0.073(2) Uani 1 1 d . . . H27 H 0.0893 0.5081 -0.0429 0.088 Uiso 1 1 calc R . . C28 C 0.0532(5) 0.6448(8) -0.0211(5) 0.085(3) Uani 1 1 d . . . H28 H -0.0091 0.6405 -0.0566 0.102 Uiso 1 1 calc R . . C29 C 0.0843(5) 0.7285(7) 0.0215(5) 0.078(2) Uani 1 1 d . . . H29 H 0.0436 0.7814 0.0149 0.094 Uiso 1 1 calc R . . C30 C 0.1759(4) 0.7360(5) 0.0748(4) 0.0547(16) Uani 1 1 d . . . H30 H 0.1973 0.7942 0.1037 0.066 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 0.0267(3) 0.0332(3) 0.0154(3) -0.0017(2) 0.0047(2) -0.0065(2) Zn2 0.0263(3) 0.0272(3) 0.0172(3) -0.0008(2) 0.0045(2) 0.0009(2) O1 0.081(3) 0.034(2) 0.129(5) -0.009(3) 0.065(3) -0.006(2) O2 0.039(2) 0.031(2) 0.056(2) -0.0016(18) 0.0111(18) -0.0018(16) O3 0.0364(19) 0.052(2) 0.0244(18) -0.0085(16) -0.0022(15) 0.0060(17) O4 0.043(2) 0.055(3) 0.0270(19) -0.0079(17) 0.0119(16) -0.0067(18) O5 0.0362(19) 0.032(2) 0.043(2) 0.0048(16) 0.0059(16) -0.0043(15) O6 0.0334(19) 0.030(2) 0.054(2) 0.0094(17) 0.0036(16) 0.0028(15) N1 0.031(2) 0.024(2) 0.038(2) 0.0007(18) 0.0089(18) 0.0048(17) N2 0.039(2) 0.028(2) 0.049(3) 0.001(2) 0.014(2) -0.0078(19) N3 0.039(2) 0.043(2) 0.017(2) -0.0081(18) 0.0044(17) 0.0045(19) N4 0.036(2) 0.037(2) 0.0153(19) -0.0061(16) 0.0064(16) 0.0002(18) N5 0.029(2) 0.031(2) 0.028(2) 0.0069(18) -0.0039(17) -0.0045(17) N6 0.030(2) 0.029(2) 0.031(2) 0.0107(18) -0.0006(17) -0.0013(17) C1 0.036(3) 0.040(3) 0.053(3) -0.002(3) 0.016(3) 0.002(2) C2 0.034(3) 0.030(3) 0.037(3) 0.006(2) 0.008(2) -0.005(2) C3 0.038(3) 0.034(3) 0.040(3) 0.006(2) 0.004(2) -0.004(2) C4 0.031(3) 0.040(3) 0.043(3) 0.003(2) 0.006(2) -0.001(2) C5 0.037(3) 0.040(3) 0.053(4) 0.004(3) 0.015(3) 0.005(2) C6 0.048(3) 0.081(5) 0.057(4) 0.003(4) 0.018(3) 0.011(3) C7 0.072(5) 0.071(5) 0.068(5) 0.009(4) 0.042(4) 0.004(4) C8 0.042(3) 0.052(4) 0.095(6) -0.002(4) 0.034(4) -0.004(3) C9 0.036(3) 0.115(7) 0.083(6) 0.015(5) 0.014(4) 0.015(4) C10 0.037(3) 0.131(7) 0.065(4) 0.014(5) 0.017(3) 0.012(4) C11 0.035(3) 0.048(3) 0.029(3) -0.006(2) 0.006(2) 0.002(2) C12 0.026(2) 0.036(3) 0.016(2) -0.0032(19) 0.0027(17) 0.000(2) C13 0.038(3) 0.031(3) 0.028(3) -0.002(2) 0.004(2) 0.001(2) C14 0.041(3) 0.034(3) 0.026(3) -0.002(2) 0.008(2) -0.002(2) C15 0.048(3) 0.060(4) 0.051(4) 0.015(3) 0.011(3) 0.011(3) C16 0.047(4) 0.100(6) 0.043(4) 0.027(4) 0.009(3) 0.025(4) C17 0.037(4) 0.162(8) 0.034(4) 0.001(5) 0.005(3) 0.004(5) C18 0.049(4) 0.127(7) 0.067(5) -0.039(5) 0.011(4) -0.027(5) C19 0.046(3) 0.068(5) 0.070(5) -0.022(4) 0.013(3) -0.007(3) C20 0.033(3) 0.055(4) 0.026(3) 0.002(2) 0.006(2) 0.001(3) C21 0.032(3) 0.032(3) 0.034(3) 0.006(2) 0.000(2) 0.000(2) C22 0.035(3) 0.020(2) 0.029(3) -0.002(2) 0.006(2) 0.000(2) C23 0.038(3) 0.025(3) 0.026(2) 0.000(2) 0.003(2) 0.000(2) C24 0.031(2) 0.033(3) 0.027(2) 0.001(2) 0.0047(19) -0.005(2) C25 0.032(3) 0.045(3) 0.030(3) 0.009(2) 0.001(2) -0.008(2) C26 0.050(3) 0.060(4) 0.039(3) 0.004(3) -0.001(3) -0.017(3) C27 0.065(4) 0.098(6) 0.045(4) 0.006(4) -0.013(3) -0.034(4) C28 0.050(4) 0.138(8) 0.053(5) 0.028(5) -0.016(3) -0.023(5) C29 0.042(4) 0.118(7) 0.068(5) 0.029(5) -0.002(3) 0.012(4) C30 0.041(3) 0.058(4) 0.059(4) 0.014(3) -0.001(3) 0.006(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 1.942(3) 4_576 ? Zn1 O2 1.977(4) 2_745 ? Zn1 N3 1.993(4) . ? Zn1 N1 1.995(4) . ? Zn2 O6 1.936(3) 2_655 ? Zn2 N4 1.958(4) . ? Zn2 O3 1.965(3) 4_576 ? Zn2 N5 2.023(4) . ? Zn2 C23 2.575(5) 2_655 ? O1 C3 1.199(6) . ? O2 C3 1.255(6) . ? O2 Zn1 1.977(4) 2_755 ? O3 C13 1.241(6) . ? O3 Zn2 1.965(3) 4_575 ? O4 C13 1.228(6) . ? O4 Zn1 1.942(3) 4_575 ? O5 C23 1.233(5) . ? O6 C23 1.284(5) . ? O6 Zn2 1.936(3) 2_645 ? N1 C1 1.335(6) . ? N1 N2 1.372(5) . ? N2 C4 1.330(6) . ? N2 H2 0.8600 . ? N3 C11 1.301(6) . ? N3 N4 1.415(5) . ? N4 C14 1.338(6) . ? N5 C21 1.317(6) . ? N5 N6 1.350(5) . ? N6 C24 1.346(6) . ? N6 H3 0.8600 . ? C1 C2 1.405(7) . ? C1 H1 0.9300 . ? C2 C4 1.372(7) . ? C2 C3 1.503(7) . ? C4 C5 1.503(7) . ? C5 C10 1.359(8) . ? C5 C6 1.373(8) . ? C6 C7 1.393(8) . ? C6 H6 0.9300 . ? C7 C8 1.358(9) . ? C7 H7 0.9300 . ? C8 C9 1.330(9) . ? C8 H8 0.9300 . ? C9 C10 1.397(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.409(6) . ? C11 H11 0.9300 . ? C12 C14 1.391(6) . ? C12 C13 1.479(6) . ? C14 C20 1.485(7) . ? C15 C20 1.363(8) . ? C15 C16 1.372(8) . ? C15 H15 0.9300 . ? C16 C17 1.352(11) . ? C16 H16 0.9300 . ? C17 C18 1.366(11) . ? C17 H17 0.9300 . ? C18 C19 1.409(9) . ? C18 H18 0.9300 . ? C19 C20 1.386(8) . ? C19 H19 0.9300 . ? C21 C22 1.387(6) . ? C21 H21 0.9300 . ? C22 C24 1.393(6) . ? C22 C23 1.470(6) . ? C23 Zn2 2.575(5) 2_645 ? C24 C25 1.468(7) . ? C25 C26 1.376(8) . ? C25 C30 1.382(8) . ? C26 C27 1.395(8) . ? C26 H26 0.9300 . ? C27 C28 1.371(11) . ? C27 H27 0.9300 . ? C28 C29 1.345(11) . ? C28 H28 0.9300 . ? C29 C30 1.376(8) . ? C29 H29 0.9300 . ? C30 H30 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 95.46(15) 4_576 2_745 ? O4 Zn1 N3 126.95(16) 4_576 . ? O2 Zn1 N3 97.56(16) 2_745 . ? O4 Zn1 N1 115.61(16) 4_576 . ? O2 Zn1 N1 106.52(15) 2_745 . ? N3 Zn1 N1 109.31(17) . . ? O6 Zn2 N4 122.40(16) 2_655 . ? O6 Zn2 O3 110.07(16) 2_655 4_576 ? N4 Zn2 O3 111.66(16) . 4_576 ? O6 Zn2 N5 108.18(15) 2_655 . ? N4 Zn2 N5 106.63(16) . . ? O3 Zn2 N5 93.96(15) 4_576 . ? O6 Zn2 C23 28.87(14) 2_655 2_655 ? N4 Zn2 C23 109.19(16) . 2_655 ? O3 Zn2 C23 95.99(15) 4_576 2_655 ? N5 Zn2 C23 135.87(16) . 2_655 ? C3 O2 Zn1 136.3(4) . 2_755 ? C13 O3 Zn2 138.9(3) . 4_575 ? C13 O4 Zn1 125.0(3) . 4_575 ? C23 O6 Zn2 104.4(3) . 2_645 ? C1 N1 N2 104.2(4) . . ? C1 N1 Zn1 136.4(3) . . ? N2 N1 Zn1 118.7(3) . . ? C4 N2 N1 112.3(4) . . ? C4 N2 H2 123.9 . . ? N1 N2 H2 123.9 . . ? C11 N3 N4 107.3(4) . . ? C11 N3 Zn1 129.1(3) . . ? N4 N3 Zn1 123.6(3) . . ? C14 N4 N3 107.7(4) . . ? C14 N4 Zn2 132.9(3) . . ? N3 N4 Zn2 118.8(3) . . ? C21 N5 N6 104.5(4) . . ? C21 N5 Zn2 122.2(3) . . ? N6 N5 Zn2 133.2(3) . . ? C24 N6 N5 112.9(4) . . ? C24 N6 H3 123.6 . . ? N5 N6 H3 123.6 . . ? N1 C1 C2 111.1(5) . . ? N1 C1 H1 124.4 . . ? C2 C1 H1 124.4 . . ? C4 C2 C1 105.1(4) . . ? C4 C2 C3 129.8(4) . . ? C1 C2 C3 124.9(5) . . ? O1 C3 O2 126.3(5) . . ? O1 C3 C2 120.2(5) . . ? O2 C3 C2 113.5(5) . . ? N2 C4 C2 107.4(4) . . ? N2 C4 C5 120.6(5) . . ? C2 C4 C5 132.1(5) . . ? C10 C5 C6 118.2(5) . . ? C10 C5 C4 121.0(5) . . ? C6 C5 C4 120.7(5) . . ? C5 C6 C7 120.6(6) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.0(6) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 119.6(6) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 121.3(6) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C5 C10 C9 120.2(7) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N3 C11 C12 111.2(4) . . ? N3 C11 H11 124.4 . . ? C12 C11 H11 124.4 . . ? C14 C12 C11 104.1(4) . . ? C14 C12 C13 130.2(4) . . ? C11 C12 C13 125.5(4) . . ? O4 C13 O3 126.0(5) . . ? O4 C13 C12 117.6(4) . . ? O3 C13 C12 116.4(4) . . ? N4 C14 C12 109.7(4) . . ? N4 C14 C20 118.9(4) . . ? C12 C14 C20 131.5(4) . . ? C20 C15 C16 121.3(7) . . ? C20 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 120.9(7) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.0(6) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 119.4(7) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 120.0(7) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C15 C20 C19 118.4(5) . . ? C15 C20 C14 120.1(5) . . ? C19 C20 C14 121.5(5) . . ? N5 C21 C22 112.3(4) . . ? N5 C21 H21 123.8 . . ? C22 C21 H21 123.8 . . ? C21 C22 C24 104.8(4) . . ? C21 C22 C23 124.0(4) . . ? C24 C22 C23 131.1(4) . . ? O5 C23 O6 123.6(4) . . ? O5 C23 C22 122.2(4) . . ? O6 C23 C22 114.2(4) . . ? O5 C23 Zn2 77.4(3) . 2_645 ? O6 C23 Zn2 46.7(2) . 2_645 ? C22 C23 Zn2 158.8(3) . 2_645 ? N6 C24 C22 105.6(4) . . ? N6 C24 C25 121.0(4) . . ? C22 C24 C25 133.4(4) . . ? C26 C25 C30 119.5(5) . . ? C26 C25 C24 120.2(5) . . ? C30 C25 C24 120.3(5) . . ? C25 C26 C27 119.8(6) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 119.1(7) . . ? C28 C27 H27 120.4 . . ? C26 C27 H27 120.4 . . ? C29 C28 C27 121.2(7) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 120.3(8) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C29 C30 C25 120.1(7) . . ? C29 C30 H30 120.0 . . ? C25 C30 H30 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 O4 Zn1 N1 C1 -63.1(6) 4_576 . . . ? O2 Zn1 N1 C1 -167.7(5) 2_745 . . . ? N3 Zn1 N1 C1 87.8(5) . . . . ? O4 Zn1 N1 N2 128.4(3) 4_576 . . . ? O2 Zn1 N1 N2 23.8(4) 2_745 . . . ? N3 Zn1 N1 N2 -80.6(4) . . . . ? C1 N1 N2 C4 0.8(6) . . . . ? Zn1 N1 N2 C4 172.6(3) . . . . ? O4 Zn1 N3 C11 -145.1(4) 4_576 . . . ? O2 Zn1 N3 C11 -42.4(5) 2_745 . . . ? N1 Zn1 N3 C11 68.1(5) . . . . ? O4 Zn1 N3 N4 35.0(4) 4_576 . . . ? O2 Zn1 N3 N4 137.7(4) 2_745 . . . ? N1 Zn1 N3 N4 -111.8(4) . . . . ? C11 N3 N4 C14 -2.5(5) . . . . ? Zn1 N3 N4 C14 177.5(3) . . . . ? C11 N3 N4 Zn2 169.6(3) . . . . ? Zn1 N3 N4 Zn2 -10.5(5) . . . . ? O6 Zn2 N4 C14 -89.5(5) 2_655 . . . ? O3 Zn2 N4 C14 136.9(4) 4_576 . . . ? N5 Zn2 N4 C14 35.6(5) . . . . ? C23 Zn2 N4 C14 -118.2(5) 2_655 . . . ? O6 Zn2 N4 N3 100.9(3) 2_655 . . . ? O3 Zn2 N4 N3 -32.7(4) 4_576 . . . ? N5 Zn2 N4 N3 -134.0(3) . . . . ? C23 Zn2 N4 N3 72.2(3) 2_655 . . . ? O6 Zn2 N5 C21 -140.0(4) 2_655 . . . ? N4 Zn2 N5 C21 86.6(4) . . . . ? O3 Zn2 N5 C21 -27.4(4) 4_576 . . . ? C23 Zn2 N5 C21 -130.2(4) 2_655 . . . ? O6 Zn2 N5 N6 43.7(5) 2_655 . . . ? N4 Zn2 N5 N6 -89.7(4) . . . . ? O3 Zn2 N5 N6 156.3(4) 4_576 . . . ? C23 Zn2 N5 N6 53.5(5) 2_655 . . . ? C21 N5 N6 C24 -0.6(5) . . . . ? Zn2 N5 N6 C24 176.2(3) . . . . ? N2 N1 C1 C2 -1.1(6) . . . . ? Zn1 N1 C1 C2 -170.6(4) . . . . ? N1 C1 C2 C4 1.0(6) . . . . ? N1 C1 C2 C3 -174.0(5) . . . . ? Zn1 O2 C3 O1 22.3(9) 2_755 . . . ? Zn1 O2 C3 C2 -157.3(4) 2_755 . . . ? C4 C2 C3 O1 -175.7(6) . . . . ? C1 C2 C3 O1 -2.0(9) . . . . ? C4 C2 C3 O2 3.9(8) . . . . ? C1 C2 C3 O2 177.6(5) . . . . ? N1 N2 C4 C2 -0.2(6) . . . . ? N1 N2 C4 C5 179.8(5) . . . . ? C1 C2 C4 N2 -0.4(6) . . . . ? C3 C2 C4 N2 174.2(5) . . . . ? C1 C2 C4 C5 179.6(6) . . . . ? C3 C2 C4 C5 -5.8(10) . . . . ? N2 C4 C5 C10 -75.3(8) . . . . ? C2 C4 C5 C10 104.7(8) . . . . ? N2 C4 C5 C6 105.3(7) . . . . ? C2 C4 C5 C6 -74.7(8) . . . . ? C10 C5 C6 C7 3.7(10) . . . . ? C4 C5 C6 C7 -176.9(6) . . . . ? C5 C6 C7 C8 -3.2(11) . . . . ? C6 C7 C8 C9 1.1(11) . . . . ? C7 C8 C9 C10 0.4(12) . . . . ? C6 C5 C10 C9 -2.2(11) . . . . ? C4 C5 C10 C9 178.4(7) . . . . ? C8 C9 C10 C5 0.1(12) . . . . ? N4 N3 C11 C12 3.1(6) . . . . ? Zn1 N3 C11 C12 -176.8(3) . . . . ? N3 C11 C12 C14 -2.6(6) . . . . ? N3 C11 C12 C13 172.3(5) . . . . ? Zn1 O4 C13 O3 12.7(8) 4_575 . . . ? Zn1 O4 C13 C12 -164.6(3) 4_575 . . . ? Zn2 O3 C13 O4 31.8(9) 4_575 . . . ? Zn2 O3 C13 C12 -150.8(4) 4_575 . . . ? C14 C12 C13 O4 -175.3(5) . . . . ? C11 C12 C13 O4 11.2(8) . . . . ? C14 C12 C13 O3 7.1(8) . . . . ? C11 C12 C13 O3 -166.4(5) . . . . ? N3 N4 C14 C12 0.8(5) . . . . ? Zn2 N4 C14 C12 -169.6(3) . . . . ? N3 N4 C14 C20 -179.0(4) . . . . ? Zn2 N4 C14 C20 10.5(7) . . . . ? C11 C12 C14 N4 1.0(6) . . . . ? C13 C12 C14 N4 -173.6(5) . . . . ? C11 C12 C14 C20 -179.2(5) . . . . ? C13 C12 C14 C20 6.2(9) . . . . ? C20 C15 C16 C17 0.4(9) . . . . ? C15 C16 C17 C18 -1.0(10) . . . . ? C16 C17 C18 C19 -0.5(11) . . . . ? C17 C18 C19 C20 2.6(11) . . . . ? C16 C15 C20 C19 1.8(9) . . . . ? C16 C15 C20 C14 -177.4(5) . . . . ? C18 C19 C20 C15 -3.2(9) . . . . ? C18 C19 C20 C14 175.9(6) . . . . ? N4 C14 C20 C15 56.7(7) . . . . ? C12 C14 C20 C15 -123.0(6) . . . . ? N4 C14 C20 C19 -122.4(6) . . . . ? C12 C14 C20 C19 57.8(8) . . . . ? N6 N5 C21 C22 -0.1(6) . . . . ? Zn2 N5 C21 C22 -177.3(3) . . . . ? N5 C21 C22 C24 0.7(6) . . . . ? N5 C21 C22 C23 -175.6(4) . . . . ? Zn2 O6 C23 O5 10.0(6) 2_645 . . . ? Zn2 O6 C23 C22 -168.9(3) 2_645 . . . ? C21 C22 C23 O5 159.3(5) . . . . ? C24 C22 C23 O5 -15.9(8) . . . . ? C21 C22 C23 O6 -21.7(7) . . . . ? C24 C22 C23 O6 163.0(5) . . . . ? C21 C22 C23 Zn2 -44.5(12) . . . 2_645 ? C24 C22 C23 Zn2 140.2(8) . . . 2_645 ? N5 N6 C24 C22 1.0(5) . . . . ? N5 N6 C24 C25 -178.1(4) . . . . ? C21 C22 C24 N6 -0.9(5) . . . . ? C23 C22 C24 N6 175.0(5) . . . . ? C21 C22 C24 C25 178.0(5) . . . . ? C23 C22 C24 C25 -6.1(9) . . . . ? N6 C24 C25 C26 139.4(5) . . . . ? C22 C24 C25 C26 -39.4(8) . . . . ? N6 C24 C25 C30 -37.3(7) . . . . ? C22 C24 C25 C30 143.9(6) . . . . ? C30 C25 C26 C27 -2.5(9) . . . . ? C24 C25 C26 C27 -179.2(5) . . . . ? C25 C26 C27 C28 1.5(10) . . . . ? C26 C27 C28 C29 -0.1(11) . . . . ? C27 C28 C29 C30 -0.4(12) . . . . ? C28 C29 C30 C25 -0.6(11) . . . . ? C26 C25 C30 C29 2.0(9) . . . . ? C24 C25 C30 C29 178.7(6) . . . . ? 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 N2 H2 O1 0.86 1.83 2.656(6) 159.2 2_745 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.952 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.136