# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yue-Peng Cai' _publ_contact_author_email ypcaizsu@yahoo.com loop_ _publ_author_name 'Ming-Fang Wang' 'Xu-Jia Hong' 'Qing-Guang Zhan' 'Hong-Guang Jin' ; Yi-Ting Liu ; 'Zhi-Peng Zheng' 'Shi-Hai Xu' 'Yue-Peng Cai' ################ END ################ data_849600(9) _database_code_depnum_ccdc_archive 'CCDC 849592' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cd Cl N O4' _chemical_formula_weight 378.04 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.433(9) _cell_length_b 18.004(10) _cell_length_c 9.215(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.158(8) _cell_angle_gamma 90.00 _cell_volume 2560(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 472 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 18.85 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.962 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.922 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6349 _exptl_absorpt_correction_T_max 0.8021 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 6319 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.2403 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2312 _reflns_number_gt 837 _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^)+(0.0298P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2312 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2280 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.1385 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 Cd1 Cd 0.11498(3) 0.01137(2) 0.50290(6) 0.06051(16) Uani 1 1 d . . . Cl1 Cl -0.01059(11) 0.09988(9) 0.4756(2) 0.0794(8) Uani 1 1 d . . . O1 O 0.4019(3) 0.1816(2) 0.9378(5) 0.104(2) Uani 1 1 d . . . O2 O 0.4018(3) 0.0611(3) 0.9036(5) 0.105(2) Uani 1 1 d . . . O3 O 0.2225(3) 0.0714(2) 0.9194(5) 0.0716(17) Uani 1 1 d . . . O4 O 0.1508(2) 0.0105(2) 0.7469(5) 0.0735(16) Uani 1 1 d . . . N1 N 0.2268(3) 0.0987(2) 0.5414(5) 0.0556(19) Uani 1 1 d . . . C7 C 0.2061(4) 0.0555(3) 0.7862(7) 0.066(3) Uani 1 1 d . . . C5 C 0.2616(4) 0.0971(3) 0.6766(8) 0.071(3) Uani 1 1 d . . . C3 C 0.3805(4) 0.1795(3) 0.6112(7) 0.067(3) Uani 1 1 d . . . H3 H 0.4318 0.2043 0.6347 0.081 Uiso 1 1 calc R . . C4 C 0.3421(4) 0.1363(3) 0.7117(7) 0.062(2) Uani 1 1 d . . . C6 C 0.3819(4) 0.1280(3) 0.8623(9) 0.085(3) Uani 1 1 d . . . C1 C 0.2643(4) 0.1431(3) 0.4468(7) 0.060(2) Uani 1 1 d . . . C9 C 0.2611(4) 0.1970(3) 0.2077(7) 0.078(3) Uani 1 1 d . . . H9 H 0.2332 0.2024 0.1179 0.094 Uiso 1 1 calc R . . C2 C 0.3435(4) 0.1868(3) 0.4729(7) 0.055(2) Uani 1 1 d . . . C8 C 0.2264(5) 0.1519(3) 0.3058(7) 0.079(3) Uani 1 1 d . . . H8 H 0.1763 0.1255 0.2814 0.095 Uiso 1 1 calc R . . C11 C 0.3788(5) 0.2340(3) 0.3714(8) 0.086(3) Uani 1 1 d . . . H11 H 0.4274 0.2622 0.3958 0.103 Uiso 1 1 calc R . . C10 C 0.3429(5) 0.2391(3) 0.2370(8) 0.094(3) Uani 1 1 d . . . H10 H 0.3681 0.2678 0.1654 0.113 Uiso 1 1 calc R . . C12 C 0.4219(5) 0.0577(4) 1.0732(9) 0.137(4) Uani 1 1 d . . . H12A H 0.4711 0.0885 1.0962 0.206 Uiso 1 1 calc R . . H12B H 0.4342 0.0074 1.1011 0.206 Uiso 1 1 calc R . . H12C H 0.3725 0.0753 1.1248 0.206 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 Cd1 0.0476(3) 0.0616(3) 0.0726(4) -0.0056(4) 0.0080(2) -0.0022(3) Cl1 0.0545(12) 0.0596(11) 0.1244(18) -0.0099(12) 0.0092(12) 0.0008(10) O1 0.105(4) 0.116(4) 0.090(4) -0.001(3) 0.003(3) -0.018(3) O2 0.086(4) 0.136(4) 0.094(4) 0.029(3) -0.004(3) 0.019(3) O3 0.070(3) 0.073(3) 0.072(4) 0.009(3) 0.003(3) -0.008(3) O4 0.069(3) 0.074(3) 0.078(3) -0.011(3) 0.000(3) -0.015(3) N1 0.055(4) 0.061(3) 0.052(4) -0.008(3) 0.009(3) 0.006(3) C7 0.077(5) 0.066(4) 0.056(5) 0.011(4) 0.013(4) 0.011(4) C5 0.072(5) 0.072(4) 0.070(6) -0.018(4) 0.023(4) -0.007(4) C3 0.066(5) 0.078(4) 0.058(5) -0.005(4) 0.025(4) -0.029(4) C4 0.070(5) 0.081(5) 0.036(5) -0.007(4) -0.010(4) 0.012(4) C6 0.066(5) 0.063(4) 0.127(7) 0.038(5) 0.034(5) -0.001(4) C1 0.043(4) 0.092(5) 0.046(5) -0.012(4) 0.017(4) 0.030(4) C9 0.105(6) 0.054(4) 0.076(6) 0.008(4) 0.006(5) 0.003(4) C2 0.042(4) 0.055(4) 0.068(5) -0.004(4) 0.022(4) 0.008(3) C8 0.109(6) 0.053(4) 0.075(6) 0.005(4) 0.031(5) -0.025(4) C11 0.133(7) 0.070(4) 0.055(5) 0.010(4) 0.032(5) -0.007(5) C10 0.173(8) 0.040(4) 0.071(6) 0.006(4) 0.043(6) -0.011(5) C12 0.114(7) 0.102(6) 0.196(10) 0.027(7) -0.012(7) 0.021(6) _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 Cd1 O4 2.304(4) . ? Cd1 N1 2.356(5) . ? Cd1 O3 2.370(4) 6 ? Cd1 O4 2.466(4) 6 ? Cd1 Cl1 2.518(2) . ? Cd1 Cl1 2.581(2) 5_556 ? Cd1 C7 2.744(7) 6 ? Cl1 Cd1 2.581(2) 5_556 ? O1 C6 1.226(8) . ? O2 C6 1.297(7) . ? O2 C12 1.588(10) . ? O3 C7 1.281(8) . ? O3 Cd1 2.370(4) 6_556 ? O4 C7 1.226(7) . ? O4 Cd1 2.466(4) 6_556 ? N1 C1 1.325(8) . ? N1 C5 1.347(8) . ? C7 C5 1.533(9) . ? C7 Cd1 2.744(7) 6_556 ? C5 C4 1.460(9) . ? C3 C4 1.354(8) . ? C3 C2 1.392(8) . ? C3 H3 0.9300 . ? C4 C6 1.513(10) . ? C1 C8 1.422(9) . ? C1 C2 1.471(8) . ? C9 C8 1.336(9) . ? C9 C10 1.492(9) . ? C9 H9 0.9300 . ? C2 C11 1.383(9) . ? C8 H8 0.9300 . ? C11 C10 1.350(10) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 Cd1 N1 72.36(15) . . ? O4 Cd1 O3 99.03(14) . 6 ? N1 Cd1 O3 87.29(15) . 6 ? O4 Cd1 O4 151.48(17) . 6 ? N1 Cd1 O4 94.19(15) . 6 ? O3 Cd1 O4 54.35(13) 6 6 ? O4 Cd1 Cl1 105.70(11) . . ? N1 Cd1 Cl1 98.80(12) . . ? O3 Cd1 Cl1 155.23(12) 6 . ? O4 Cd1 Cl1 101.09(10) 6 . ? O4 Cd1 Cl1 93.30(11) . 5_556 ? N1 Cd1 Cl1 164.33(12) . 5_556 ? O3 Cd1 Cl1 88.81(11) 6 5_556 ? O4 Cd1 Cl1 95.84(10) 6 5_556 ? Cl1 Cd1 Cl1 91.06(7) . 5_556 ? O4 Cd1 C7 126.22(17) . 6 ? N1 Cd1 C7 91.00(18) . 6 ? O3 Cd1 C7 27.80(16) 6 6 ? O4 Cd1 C7 26.55(15) 6 6 ? Cl1 Cd1 C7 127.57(15) . 6 ? Cl1 Cd1 C7 92.61(14) 5_556 6 ? Cd1 Cl1 Cd1 88.94(7) . 5_556 ? C6 O2 C12 111.4(6) . . ? C7 O3 Cd1 92.6(4) . 6_556 ? C7 O4 Cd1 115.8(4) . . ? C7 O4 Cd1 89.5(4) . 6_556 ? Cd1 O4 Cd1 151.73(18) . 6_556 ? C1 N1 C5 116.8(5) . . ? C1 N1 Cd1 129.2(4) . . ? C5 N1 Cd1 113.7(4) . . ? O4 C7 O3 123.6(6) . . ? O4 C7 C5 121.5(6) . . ? O3 C7 C5 114.9(6) . . ? O4 C7 Cd1 64.0(3) . 6_556 ? O3 C7 Cd1 59.6(3) . 6_556 ? C5 C7 Cd1 174.5(5) . 6_556 ? N1 C5 C4 121.1(6) . . ? N1 C5 C7 113.7(6) . . ? C4 C5 C7 125.1(6) . . ? C4 C3 C2 120.2(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.5(6) . . ? C3 C4 C6 120.6(6) . . ? C5 C4 C6 118.9(6) . . ? O1 C6 O2 120.6(7) . . ? O1 C6 C4 122.3(6) . . ? O2 C6 C4 116.8(6) . . ? N1 C1 C8 119.4(6) . . ? N1 C1 C2 126.0(6) . . ? C8 C1 C2 114.6(6) . . ? C8 C9 C10 122.4(6) . . ? C8 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C11 C2 C3 121.2(6) . . ? C11 C2 C1 123.7(6) . . ? C3 C2 C1 115.0(5) . . ? C9 C8 C1 121.5(6) . . ? C9 C8 H8 119.3 . . ? C1 C8 H8 119.3 . . ? C10 C11 C2 120.2(7) . . ? C10 C11 H11 119.9 . . ? C2 C11 H11 119.9 . . ? C11 C10 C9 117.5(6) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 O4 Cd1 Cl1 Cd1 -93.73(11) . . . 5_556 ? N1 Cd1 Cl1 Cd1 -167.77(13) . . . 5_556 ? O3 Cd1 Cl1 Cd1 89.4(2) 6 . . 5_556 ? O4 Cd1 Cl1 Cd1 96.17(10) 6 . . 5_556 ? Cl1 Cd1 Cl1 Cd1 0.0 5_556 . . 5_556 ? C7 Cd1 Cl1 Cd1 94.11(17) 6 . . 5_556 ? N1 Cd1 O4 C7 2.8(4) . . . . ? O3 Cd1 O4 C7 87.1(4) 6 . . . ? O4 Cd1 O4 C7 67.7(4) 6 . . . ? Cl1 Cd1 O4 C7 -91.6(4) . . . . ? Cl1 Cd1 O4 C7 176.4(4) 5_556 . . . ? C7 Cd1 O4 C7 80.7(6) 6 . . . ? N1 Cd1 O4 Cd1 154.4(4) . . . 6_556 ? O3 Cd1 O4 Cd1 -121.4(4) 6 . . 6_556 ? O4 Cd1 O4 Cd1 -140.7(4) 6 . . 6_556 ? Cl1 Cd1 O4 Cd1 59.9(4) . . . 6_556 ? Cl1 Cd1 O4 Cd1 -32.1(4) 5_556 . . 6_556 ? C7 Cd1 O4 Cd1 -127.8(4) 6 . . 6_556 ? O4 Cd1 N1 C1 -178.7(5) . . . . ? O3 Cd1 N1 C1 81.0(5) 6 . . . ? O4 Cd1 N1 C1 27.0(5) 6 . . . ? Cl1 Cd1 N1 C1 -74.9(5) . . . . ? Cl1 Cd1 N1 C1 156.8(4) 5_556 . . . ? C7 Cd1 N1 C1 53.4(5) 6 . . . ? O4 Cd1 N1 C5 8.0(4) . . . . ? O3 Cd1 N1 C5 -92.3(4) 6 . . . ? O4 Cd1 N1 C5 -146.3(4) 6 . . . ? Cl1 Cd1 N1 C5 111.8(4) . . . . ? Cl1 Cd1 N1 C5 -16.6(7) 5_556 . . . ? C7 Cd1 N1 C5 -119.9(4) 6 . . . ? Cd1 O4 C7 O3 167.3(5) . . . . ? Cd1 O4 C7 O3 0.3(6) 6_556 . . . ? Cd1 O4 C7 C5 -12.8(7) . . . . ? Cd1 O4 C7 C5 -179.8(5) 6_556 . . . ? Cd1 O4 C7 Cd1 167.0(3) . . . 6_556 ? Cd1 O3 C7 O4 -0.4(6) 6_556 . . . ? Cd1 O3 C7 C5 179.8(5) 6_556 . . . ? C1 N1 C5 C4 -6.5(8) . . . . ? Cd1 N1 C5 C4 167.7(4) . . . . ? C1 N1 C5 C7 169.9(5) . . . . ? Cd1 N1 C5 C7 -15.9(6) . . . . ? O4 C7 C5 N1 20.3(9) . . . . ? O3 C7 C5 N1 -159.9(5) . . . . ? Cd1 C7 C5 N1 -158(4) 6_556 . . . ? O4 C7 C5 C4 -163.5(6) . . . . ? O3 C7 C5 C4 16.3(9) . . . . ? Cd1 C7 C5 C4 18(5) 6_556 . . . ? C2 C3 C4 C5 -0.1(9) . . . . ? C2 C3 C4 C6 180.0(6) . . . . ? N1 C5 C4 C3 4.6(9) . . . . ? C7 C5 C4 C3 -171.3(6) . . . . ? N1 C5 C4 C6 -175.4(6) . . . . ? C7 C5 C4 C6 8.6(9) . . . . ? C12 O2 C6 O1 19.5(9) . . . . ? C12 O2 C6 C4 -166.8(6) . . . . ? C3 C4 C6 O1 52.3(10) . . . . ? C5 C4 C6 O1 -127.7(7) . . . . ? C3 C4 C6 O2 -121.4(7) . . . . ? C5 C4 C6 O2 58.7(8) . . . . ? C5 N1 C1 C8 -174.9(6) . . . . ? Cd1 N1 C1 C8 12.0(8) . . . . ? C5 N1 C1 C2 4.4(9) . . . . ? Cd1 N1 C1 C2 -168.7(4) . . . . ? C4 C3 C2 C11 176.2(6) . . . . ? C4 C3 C2 C1 -2.0(8) . . . . ? N1 C1 C2 C11 -178.3(6) . . . . ? C8 C1 C2 C11 1.0(9) . . . . ? N1 C1 C2 C3 -0.1(9) . . . . ? C8 C1 C2 C3 179.2(5) . . . . ? C10 C9 C8 C1 2.1(10) . . . . ? N1 C1 C8 C9 178.9(6) . . . . ? C2 C1 C8 C9 -0.5(9) . . . . ? C3 C2 C11 C10 178.6(6) . . . . ? C1 C2 C11 C10 -3.3(10) . . . . ? C2 C11 C10 C9 4.6(10) . . . . ? C8 C9 C10 C11 -4.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.548 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.128 ############# END ################# ############### END ################## data_849599(8) _database_code_depnum_ccdc_archive 'CCDC 849593' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H12 Cd N2 O4' _chemical_formula_weight 456.72 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.777(8) _cell_length_b 8.059(2) _cell_length_c 15.281(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.007(4) _cell_angle_gamma 90.00 _cell_volume 3237.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 20.63 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.874 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 1.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7154 _exptl_absorpt_correction_T_max 0.8630 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 7975 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0810 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2918 _reflns_number_gt 1894 _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. U~iso~ of four carbon atoms C3, C10, C13 and C13 were restrained. ; _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^)+(0.1794P)^2^+18.1144P] 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 2918 _refine_ls_number_parameters 244 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1873 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.058 _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 Cd1 Cd 0.12695(4) -0.12339(12) 0.43024(7) 0.0361(4) Uani 1 1 d . . . O1 O 0.0776(3) 0.0215(9) 0.8096(5) 0.0247(18) Uani 1 1 d . . . O2 O 0.1434(3) 0.0893(10) 0.7775(6) 0.031(2) Uani 1 1 d . . . O3 O 0.1050(3) 0.5265(9) 0.3728(6) 0.0304(19) Uani 1 1 d . . . O4 O 0.1658(3) 0.6755(9) 0.4807(6) 0.0251(18) Uani 1 1 d . . . N1 N 0.0800(3) -0.1245(9) 0.5098(5) 0.0094(16) Uani 1 1 d . . . N2 N 0.1732(3) 0.0882(9) 0.4939(6) 0.0123(17) Uani 1 1 d . . . C1 C 0.0988(4) -0.0565(12) 0.5944(7) 0.012(2) Uani 1 1 d . . . H1 H 0.1296 -0.0009 0.6129 0.015 Uiso 1 1 calc R . . C2 C 0.0759(4) -0.0614(13) 0.6591(7) 0.016(2) Uani 1 1 d . . . C3 C 0.1023(4) 0.0255(13) 0.7563(8) 0.020(2) Uani 1 1 d U . . C4 C 0.0307(4) -0.1434(14) 0.6327(8) 0.022(2) Uani 1 1 d . . . H4 H 0.0146 -0.1493 0.6745 0.027 Uiso 1 1 calc R . . C5 C 0.0086(4) -0.2192(13) 0.5417(7) 0.016(2) Uani 1 1 d . . . C6 C -0.0381(4) -0.3063(15) 0.5107(9) 0.029(3) Uani 1 1 d . . . H6 H -0.0546 -0.3179 0.5515 0.035 Uiso 1 1 calc R . . C7 C -0.0593(4) -0.3745(15) 0.4192(9) 0.030(3) Uani 1 1 d . . . H7 H -0.0901 -0.4313 0.3986 0.036 Uiso 1 1 calc R . . C8 C -0.0343(4) -0.3572(13) 0.3588(8) 0.024(2) Uani 1 1 d . . . H8 H -0.0493 -0.4001 0.2971 0.029 Uiso 1 1 calc R . . C9 C 0.0111(4) -0.2796(12) 0.3875(7) 0.016(2) Uani 1 1 d . . . H9 H 0.0276 -0.2733 0.3464 0.020 Uiso 1 1 calc R . . C10 C 0.0341(3) -0.2069(12) 0.4812(7) 0.012(2) Uani 1 1 d U . . C11 C 0.1523(3) 0.2316(11) 0.4559(7) 0.0106(19) Uani 1 1 d . . . H11 H 0.1221 0.2293 0.4011 0.013 Uiso 1 1 calc R . . C12 C 0.1729(4) 0.3866(12) 0.4932(7) 0.013(2) Uani 1 1 d U . . C13 C 0.1453(4) 0.5419(14) 0.4428(8) 0.022(2) Uani 1 1 d U . . C14 C 0.2171(4) 0.3922(12) 0.5731(7) 0.018(2) Uani 1 1 d . . . H14 H 0.2312 0.4937 0.5998 0.021 Uiso 1 1 calc R . . C15 C 0.2418(4) 0.2410(13) 0.6157(7) 0.016(2) Uani 1 1 d . . . C16 C 0.2881(4) 0.2420(15) 0.6971(8) 0.027(3) Uani 1 1 d . . . H16 H 0.3033 0.3422 0.7239 0.032 Uiso 1 1 calc R . . C17 C 0.3108(5) 0.0960(17) 0.7367(9) 0.036(3) Uani 1 1 d . . . H17 H 0.3408 0.0953 0.7919 0.043 Uiso 1 1 calc R . . C18 C 0.2879(5) -0.0548(16) 0.6924(9) 0.033(3) Uani 1 1 d . . . H18 H 0.3042 -0.1542 0.7178 0.039 Uiso 1 1 calc R . . C19 C 0.2434(4) -0.0593(13) 0.6147(8) 0.021(2) Uani 1 1 d . . . H19 H 0.2290 -0.1604 0.5878 0.025 Uiso 1 1 calc R . . C20 C 0.2191(4) 0.0896(12) 0.5752(7) 0.013(2) 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 Cd1 0.0389(7) 0.0294(6) 0.0381(6) 0.0027(4) 0.0140(5) -0.0002(4) O1 0.034(5) 0.029(4) 0.016(4) -0.002(3) 0.014(3) 0.013(4) O2 0.037(5) 0.034(5) 0.019(4) -0.011(3) 0.007(4) -0.005(4) O3 0.034(5) 0.015(4) 0.040(5) 0.009(3) 0.012(4) 0.009(3) O4 0.032(5) 0.008(4) 0.035(5) -0.003(3) 0.013(4) 0.000(3) N1 0.009(4) 0.010(4) 0.008(4) -0.003(3) 0.002(3) -0.001(3) N2 0.014(4) 0.008(4) 0.016(4) 0.001(3) 0.007(4) 0.000(3) C1 0.010(5) 0.009(4) 0.017(5) 0.003(4) 0.005(4) 0.000(4) C2 0.017(5) 0.017(5) 0.015(5) -0.005(4) 0.007(4) 0.004(4) C3 0.021(2) 0.020(2) 0.020(2) -0.0002(10) 0.0077(13) 0.0009(10) C4 0.026(6) 0.028(6) 0.018(5) 0.004(5) 0.014(5) 0.010(5) C5 0.014(5) 0.016(5) 0.018(5) -0.001(4) 0.005(4) 0.004(4) C6 0.011(5) 0.026(6) 0.050(8) 0.012(6) 0.013(5) -0.002(5) C7 0.010(5) 0.032(7) 0.037(7) 0.006(6) -0.003(5) -0.011(5) C8 0.019(6) 0.018(6) 0.023(6) -0.009(5) -0.004(5) -0.004(5) C9 0.019(5) 0.018(5) 0.010(5) 0.003(4) 0.004(4) 0.006(4) C10 0.012(2) 0.012(2) 0.012(2) 0.0002(10) 0.0045(12) 0.0003(10) C11 0.005(5) 0.007(5) 0.018(5) -0.002(4) 0.002(4) -0.003(4) C12 0.014(2) 0.013(2) 0.014(2) 0.0003(10) 0.0057(12) 0.0001(10) C13 0.022(2) 0.022(3) 0.022(2) 0.0003(10) 0.0094(13) 0.0008(10) C14 0.017(5) 0.013(5) 0.021(6) -0.006(4) 0.006(5) -0.002(4) C15 0.011(5) 0.015(5) 0.021(5) -0.002(4) 0.007(4) -0.004(4) C16 0.009(5) 0.026(6) 0.034(7) -0.004(5) -0.003(5) 0.002(5) C17 0.019(6) 0.049(8) 0.027(7) -0.001(6) -0.004(5) -0.010(6) C18 0.028(7) 0.031(7) 0.045(8) 0.012(6) 0.020(6) 0.017(6) C19 0.017(5) 0.013(5) 0.030(6) 0.005(5) 0.006(5) 0.005(4) C20 0.007(5) 0.014(5) 0.020(5) 0.006(4) 0.008(4) 0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O4 1.942(7) 1_545 ? Cd1 O1 1.990(8) 6 ? Cd1 N2 2.138(8) . ? Cd1 N1 2.155(7) . ? Cd1 C3 2.580(11) 6 ? Cd1 O2 2.577(8) 6 ? Cd1 C13 2.740(11) 1_545 ? O1 C3 1.281(13) . ? O1 Cd1 1.990(8) 6_556 ? O2 C3 1.205(13) . ? O2 Cd1 2.577(8) 6_556 ? O3 C13 1.222(14) . ? O4 C13 1.251(13) . ? O4 Cd1 1.942(7) 1_565 ? N1 C1 1.301(12) . ? N1 C10 1.380(12) . ? N2 C11 1.323(12) . ? N2 C20 1.397(13) . ? C1 C2 1.393(13) . ? C1 H1 0.9300 . ? C2 C4 1.366(15) . ? C2 C3 1.535(14) . ? C3 Cd1 2.580(11) 6_556 ? C4 C5 1.412(15) . ? C4 H4 0.9300 . ? C5 C10 1.398(14) . ? C5 C6 1.416(14) . ? C6 C7 1.390(18) . ? C6 H6 0.9300 . ? C7 C8 1.389(17) . ? C7 H7 0.9300 . ? C8 C9 1.352(15) . ? C8 H8 0.9300 . ? C9 C10 1.436(13) . ? C9 H9 0.9300 . ? C11 C12 1.401(13) . ? C11 H11 0.9300 . ? C12 C14 1.359(14) . ? C12 C13 1.515(15) . ? C13 Cd1 2.740(11) 1_565 ? C14 C15 1.427(14) . ? C14 H14 0.9300 . ? C15 C16 1.406(14) . ? C15 C20 1.404(14) . ? C16 C17 1.362(17) . ? C16 H16 0.9300 . ? C17 C18 1.416(18) . ? C17 H17 0.9300 . ? C18 C19 1.347(17) . ? C18 H18 0.9300 . ? C19 C20 1.396(14) . ? C19 H19 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 Cd1 O1 142.3(3) 1_545 6 ? O4 Cd1 N2 109.5(3) 1_545 . ? O1 Cd1 N2 99.8(3) 6 . ? O4 Cd1 N1 99.5(3) 1_545 . ? O1 Cd1 N1 98.6(3) 6 . ? N2 Cd1 N1 99.5(3) . . ? O4 Cd1 C3 122.4(3) 1_545 6 ? O1 Cd1 C3 29.1(3) 6 6 ? N2 Cd1 C3 94.8(3) . 6 ? N1 Cd1 C3 127.6(3) . 6 ? O4 Cd1 O2 99.2(3) 1_545 6 ? O1 Cd1 O2 56.0(3) 6 6 ? N2 Cd1 O2 91.0(3) . 6 ? N1 Cd1 O2 154.1(3) . 6 ? C3 Cd1 O2 27.0(3) 6 6 ? O4 Cd1 C13 24.1(3) 1_545 1_545 ? O1 Cd1 C13 121.0(3) 6 1_545 ? N2 Cd1 C13 133.4(3) . 1_545 ? N1 Cd1 C13 95.9(3) . 1_545 ? C3 Cd1 C13 109.7(3) 6 1_545 ? O2 Cd1 C13 93.9(3) 6 1_545 ? C3 O1 Cd1 101.9(7) . 6_556 ? C3 O2 Cd1 76.6(6) . 6_556 ? C13 O4 Cd1 116.5(7) . 1_565 ? C1 N1 C10 118.3(8) . . ? C1 N1 Cd1 117.1(6) . . ? C10 N1 Cd1 124.2(6) . . ? C11 N2 C20 118.7(8) . . ? C11 N2 Cd1 114.1(6) . . ? C20 N2 Cd1 126.8(6) . . ? N1 C1 C2 124.6(9) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C4 C2 C1 118.1(9) . . ? C4 C2 C3 122.9(9) . . ? C1 C2 C3 118.9(9) . . ? O2 C3 O1 125.2(10) . . ? O2 C3 C2 120.0(9) . . ? O1 C3 C2 114.8(9) . . ? O2 C3 Cd1 76.4(6) . 6_556 ? O1 C3 Cd1 49.0(5) . 6_556 ? C2 C3 Cd1 163.1(7) . 6_556 ? C2 C4 C5 119.6(9) . . ? C2 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C10 C5 C4 118.2(9) . . ? C10 C5 C6 119.8(10) . . ? C4 C5 C6 122.1(10) . . ? C7 C6 C5 120.1(11) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 119.6(10) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 121.7(10) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 120.3(9) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? N1 C10 C5 121.1(9) . . ? N1 C10 C9 120.4(8) . . ? C5 C10 C9 118.5(9) . . ? N2 C11 C12 124.0(9) . . ? N2 C11 H11 118.0 . . ? C12 C11 H11 118.0 . . ? C14 C12 C11 118.8(9) . . ? C14 C12 C13 122.4(9) . . ? C11 C12 C13 118.8(9) . . ? O3 C13 O4 126.4(11) . . ? O3 C13 C12 118.4(10) . . ? O4 C13 C12 115.1(9) . . ? O3 C13 Cd1 87.2(7) . 1_565 ? O4 C13 Cd1 39.4(5) . 1_565 ? C12 C13 Cd1 153.5(7) . 1_565 ? C12 C14 C15 119.5(9) . . ? C12 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C20 119.9(10) . . ? C16 C15 C14 121.0(10) . . ? C20 C15 C14 119.0(9) . . ? C17 C16 C15 119.9(11) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 118.9(11) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 122.3(11) . . ? C19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C18 C19 C20 119.1(11) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C19 C20 N2 120.2(9) . . ? C19 C20 C15 119.7(9) . . ? N2 C20 C15 120.0(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 O4 Cd1 N1 C1 86.2(7) 1_545 . . . ? O1 Cd1 N1 C1 -127.0(7) 6 . . . ? N2 Cd1 N1 C1 -25.5(7) . . . . ? C3 Cd1 N1 C1 -129.2(7) 6 . . . ? O2 Cd1 N1 C1 -138.0(7) 6 . . . ? C13 Cd1 N1 C1 110.3(7) 1_545 . . . ? O4 Cd1 N1 C10 -86.7(7) 1_545 . . . ? O1 Cd1 N1 C10 60.0(7) 6 . . . ? N2 Cd1 N1 C10 161.5(7) . . . . ? C3 Cd1 N1 C10 57.9(8) 6 . . . ? O2 Cd1 N1 C10 49.1(11) 6 . . . ? C13 Cd1 N1 C10 -62.6(7) 1_545 . . . ? O4 Cd1 N2 C11 172.3(6) 1_545 . . . ? O1 Cd1 N2 C11 16.6(7) 6 . . . ? N1 Cd1 N2 C11 -84.0(7) . . . . ? C3 Cd1 N2 C11 45.4(7) 6 . . . ? O2 Cd1 N2 C11 72.2(7) 6 . . . ? C13 Cd1 N2 C11 168.5(6) 1_545 . . . ? O4 Cd1 N2 C20 -15.0(8) 1_545 . . . ? O1 Cd1 N2 C20 -170.8(7) 6 . . . ? N1 Cd1 N2 C20 88.7(8) . . . . ? C3 Cd1 N2 C20 -141.9(8) 6 . . . ? O2 Cd1 N2 C20 -115.1(8) 6 . . . ? C13 Cd1 N2 C20 -18.9(9) 1_545 . . . ? C10 N1 C1 C2 0.3(14) . . . . ? Cd1 N1 C1 C2 -173.1(8) . . . . ? N1 C1 C2 C4 0.2(16) . . . . ? N1 C1 C2 C3 -179.6(9) . . . . ? Cd1 O2 C3 O1 3.9(10) 6_556 . . . ? Cd1 O2 C3 C2 -175.4(10) 6_556 . . . ? Cd1 O1 C3 O2 -5.0(13) 6_556 . . . ? Cd1 O1 C3 C2 174.3(7) 6_556 . . . ? C4 C2 C3 O2 176.5(11) . . . . ? C1 C2 C3 O2 -3.7(15) . . . . ? C4 C2 C3 O1 -2.9(15) . . . . ? C1 C2 C3 O1 176.9(9) . . . . ? C4 C2 C3 Cd1 12(3) . . . 6_556 ? C1 C2 C3 Cd1 -168(2) . . . 6_556 ? C1 C2 C4 C5 -0.3(15) . . . . ? C3 C2 C4 C5 179.5(10) . . . . ? C2 C4 C5 C10 -0.1(15) . . . . ? C2 C4 C5 C6 179.8(10) . . . . ? C10 C5 C6 C7 -2.1(16) . . . . ? C4 C5 C6 C7 177.9(11) . . . . ? C5 C6 C7 C8 0.3(17) . . . . ? C6 C7 C8 C9 2.0(18) . . . . ? C7 C8 C9 C10 -2.3(16) . . . . ? C1 N1 C10 C5 -0.7(13) . . . . ? Cd1 N1 C10 C5 172.1(7) . . . . ? C1 N1 C10 C9 178.2(9) . . . . ? Cd1 N1 C10 C9 -9.0(12) . . . . ? C4 C5 C10 N1 0.7(14) . . . . ? C6 C5 C10 N1 -179.3(9) . . . . ? C4 C5 C10 C9 -178.3(9) . . . . ? C6 C5 C10 C9 1.8(14) . . . . ? C8 C9 C10 N1 -178.5(9) . . . . ? C8 C9 C10 C5 0.4(14) . . . . ? C20 N2 C11 C12 -1.2(14) . . . . ? Cd1 N2 C11 C12 172.2(7) . . . . ? N2 C11 C12 C14 0.2(14) . . . . ? N2 C11 C12 C13 179.8(9) . . . . ? Cd1 O4 C13 O3 5.9(15) 1_565 . . . ? Cd1 O4 C13 C12 -171.1(6) 1_565 . . . ? C14 C12 C13 O3 -178.1(10) . . . . ? C11 C12 C13 O3 2.3(15) . . . . ? C14 C12 C13 O4 -0.8(14) . . . . ? C11 C12 C13 O4 179.6(9) . . . . ? C14 C12 C13 Cd1 -13(2) . . . 1_565 ? C11 C12 C13 Cd1 167.0(12) . . . 1_565 ? C11 C12 C14 C15 1.1(14) . . . . ? C13 C12 C14 C15 -178.5(9) . . . . ? C12 C14 C15 C16 178.6(10) . . . . ? C12 C14 C15 C20 -1.4(14) . . . . ? C20 C15 C16 C17 -0.3(16) . . . . ? C14 C15 C16 C17 179.7(11) . . . . ? C15 C16 C17 C18 2.4(18) . . . . ? C16 C17 C18 C19 -2.9(19) . . . . ? C17 C18 C19 C20 1.1(18) . . . . ? C18 C19 C20 N2 179.1(10) . . . . ? C18 C19 C20 C15 1.0(16) . . . . ? C11 N2 C20 C19 -177.3(9) . . . . ? Cd1 N2 C20 C19 10.3(13) . . . . ? C11 N2 C20 C15 0.8(13) . . . . ? Cd1 N2 C20 C15 -171.6(7) . . . . ? C16 C15 C20 C19 -1.5(15) . . . . ? C14 C15 C20 C19 178.5(9) . . . . ? C16 C15 C20 N2 -179.5(9) . . . . ? C14 C15 C20 N2 0.4(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.323 _refine_diff_density_min -1.333 _refine_diff_density_rms 0.270 # Attachment '- eight cif files.cif' data_849592(1) _database_code_depnum_ccdc_archive 'CCDC 849594' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Co N2 O10' _chemical_formula_sum 'C22 H16 Co N2 O10' _chemical_formula_weight 527.30 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3968(14) _cell_length_b 9.1349(18) _cell_length_c 9.410(3) _cell_angle_alpha 110.547(4) _cell_angle_beta 98.240(4) _cell_angle_gamma 111.630(2) _cell_volume 525.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 408 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 19.78 _exptl_crystal_description block _exptl_crystal_colour 'light red' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 269 _exptl_absorpt_coefficient_mu 0.882 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8031 _exptl_absorpt_correction_T_max 0.8790 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2735 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.1042 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.20 _reflns_number_total 1846 _reflns_number_gt 1238 _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^)+(0.0478P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1846 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Co1 Co 0.5000 0.0000 0.5000 0.0338(4) Uani 1 2 d S . . O1 O 0.6953(6) 0.5265(4) 0.6756(4) 0.0484(11) Uani 1 1 d . . . O2 O 0.5989(5) 0.2568(4) 0.6459(4) 0.0405(10) Uani 1 1 d . . . O3 O 0.2209(5) -0.0147(4) 0.3943(4) 0.0418(10) Uani 1 1 d . . . H3B H 0.1993 0.0843 0.4284 0.063 Uiso 1 1 d R . . H3A H 0.1186 -0.1203 0.3132 0.063 Uiso 1 1 d R . . O4 O 0.8061(6) 0.7039(4) 0.5405(5) 0.0493(11) Uani 1 1 d . . . H4 H 0.7618 0.6402 0.5836 0.074 Uiso 1 1 calc R . . O5 O 0.8835(6) 0.6808(5) 0.3207(5) 0.0536(11) Uani 1 1 d . . . N1 N 0.6565(6) 0.1453(5) 0.3714(5) 0.0286(10) Uani 1 1 d . . . C1 C 0.6591(8) 0.3682(7) 0.5956(6) 0.0331(13) Uani 1 1 d . . . C2 C 0.6952(7) 0.3122(6) 0.4321(6) 0.0288(12) Uani 1 1 d . . . C3 C 0.7648(7) 0.4202(6) 0.3538(6) 0.0300(12) Uani 1 1 d . . . C4 C 0.8204(8) 0.6125(7) 0.4042(7) 0.0370(13) Uani 1 1 d . . . C5 C 0.7893(7) 0.3414(7) 0.2079(6) 0.0347(13) Uani 1 1 d . . . H5 H 0.8304 0.4068 0.1516 0.042 Uiso 1 1 calc R . . C6 C 0.7546(7) 0.1674(7) 0.1424(6) 0.0312(12) Uani 1 1 d . . . C7 C 0.7823(8) 0.0862(7) -0.0062(6) 0.0400(14) Uani 1 1 d . . . H7 H 0.8189 0.1471 -0.0669 0.048 Uiso 1 1 calc R . . C8 C 0.7548(8) -0.0815(7) -0.0585(6) 0.0417(15) Uani 1 1 d . . . H8 H 0.7718 -0.1351 -0.1563 0.050 Uiso 1 1 calc R . . C9 C 0.7013(8) -0.1760(7) 0.0308(6) 0.0416(14) Uani 1 1 d . . . H9 H 0.6870 -0.2896 -0.0069 0.050 Uiso 1 1 calc R . . C10 C 0.6699(8) -0.1024(7) 0.1731(6) 0.0372(14) Uani 1 1 d . . . H10 H 0.6340 -0.1659 0.2317 0.045 Uiso 1 1 calc R . . C11 C 0.6924(7) 0.0709(6) 0.2306(6) 0.0285(12) 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 Co1 0.0439(7) 0.0231(6) 0.0369(7) 0.0136(5) 0.0179(5) 0.0152(5) O1 0.073(3) 0.026(2) 0.049(2) 0.0127(19) 0.034(2) 0.023(2) O2 0.058(3) 0.029(2) 0.042(2) 0.0180(19) 0.029(2) 0.0195(19) O3 0.046(2) 0.027(2) 0.049(2) 0.0133(18) 0.0112(19) 0.0178(18) O4 0.065(3) 0.026(2) 0.059(3) 0.020(2) 0.023(2) 0.020(2) O5 0.068(3) 0.031(2) 0.063(3) 0.028(2) 0.025(2) 0.015(2) N1 0.032(3) 0.022(2) 0.031(2) 0.010(2) 0.010(2) 0.013(2) C1 0.036(3) 0.025(3) 0.034(3) 0.008(3) 0.013(3) 0.014(3) C2 0.029(3) 0.020(3) 0.037(3) 0.013(2) 0.013(2) 0.008(2) C3 0.023(3) 0.026(3) 0.041(3) 0.018(3) 0.009(2) 0.010(2) C4 0.037(3) 0.027(3) 0.048(4) 0.020(3) 0.010(3) 0.013(3) C5 0.034(3) 0.033(3) 0.040(3) 0.020(3) 0.011(3) 0.015(3) C6 0.026(3) 0.032(3) 0.038(3) 0.018(3) 0.012(3) 0.013(3) C7 0.038(3) 0.046(4) 0.039(3) 0.022(3) 0.017(3) 0.017(3) C8 0.042(4) 0.049(4) 0.039(3) 0.018(3) 0.023(3) 0.022(3) C9 0.047(4) 0.032(3) 0.050(4) 0.014(3) 0.024(3) 0.022(3) C10 0.047(4) 0.032(3) 0.044(3) 0.019(3) 0.024(3) 0.023(3) C11 0.022(3) 0.028(3) 0.032(3) 0.011(2) 0.009(2) 0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.027(3) 2_656 ? Co1 O2 2.027(3) . ? Co1 O3 2.093(3) . ? Co1 O3 2.093(3) 2_656 ? Co1 N1 2.228(4) 2_656 ? Co1 N1 2.228(4) . ? O1 C1 1.274(5) . ? O2 C1 1.234(6) . ? O3 H3B 0.9299 . ? O3 H3A 0.9300 . ? O4 C4 1.306(6) . ? O4 H4 0.8200 . ? O5 C4 1.208(6) . ? N1 C2 1.324(5) . ? N1 C11 1.375(6) . ? C1 C2 1.539(7) . ? C2 C3 1.423(7) . ? C3 C5 1.382(7) . ? C3 C4 1.519(7) . ? C5 C6 1.393(6) . ? C5 H5 0.9300 . ? C6 C11 1.414(7) . ? C6 C7 1.419(7) . ? C7 C8 1.357(7) . ? C7 H7 0.9300 . ? C8 C9 1.401(7) . ? C8 H8 0.9300 . ? C9 C10 1.367(7) . ? C9 H9 0.9300 . ? C10 C11 1.416(6) . ? 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 Co1 O2 180.00(14) 2_656 . ? O2 Co1 O3 90.32(14) 2_656 . ? O2 Co1 O3 89.68(14) . . ? O2 Co1 O3 89.68(14) 2_656 2_656 ? O2 Co1 O3 90.32(14) . 2_656 ? O3 Co1 O3 180.000(1) . 2_656 ? O2 Co1 N1 74.65(14) 2_656 2_656 ? O2 Co1 N1 105.35(14) . 2_656 ? O3 Co1 N1 88.96(14) . 2_656 ? O3 Co1 N1 91.04(14) 2_656 2_656 ? O2 Co1 N1 105.35(14) 2_656 . ? O2 Co1 N1 74.65(14) . . ? O3 Co1 N1 91.04(14) . . ? O3 Co1 N1 88.96(14) 2_656 . ? N1 Co1 N1 180.0 2_656 . ? C1 O2 Co1 120.4(3) . . ? Co1 O3 H3B 120.0 . . ? Co1 O3 H3A 120.0 . . ? H3B O3 H3A 120.0 . . ? C4 O4 H4 109.5 . . ? C2 N1 C11 120.3(4) . . ? C2 N1 Co1 114.2(3) . . ? C11 N1 Co1 125.2(3) . . ? O2 C1 O1 122.2(5) . . ? O2 C1 C2 118.0(4) . . ? O1 C1 C2 119.7(5) . . ? N1 C2 C3 122.9(5) . . ? N1 C2 C1 110.4(4) . . ? C3 C2 C1 126.7(4) . . ? C5 C3 C2 116.4(5) . . ? C5 C3 C4 112.8(5) . . ? C2 C3 C4 130.8(5) . . ? O5 C4 O4 120.7(5) . . ? O5 C4 C3 119.8(5) . . ? O4 C4 C3 119.4(5) . . ? C3 C5 C6 122.2(5) . . ? C3 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C11 117.8(5) . . ? C5 C6 C7 122.6(5) . . ? C11 C6 C7 119.7(5) . . ? C8 C7 C6 119.1(5) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 121.8(5) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C10 C9 C8 120.5(5) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.7(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? N1 C11 C6 120.3(4) . . ? N1 C11 C10 120.4(5) . . ? C6 C11 C10 119.2(5) . . ? 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 H3B O4 0.93 1.87 2.777(5) 164.7 2_666 O3 H3A O5 0.93 2.03 2.735(5) 131.2 1_445 O4 H4 O1 0.82 1.56 2.383(5) 175.4 . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.350 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.095 ################# END ################ data_849593(3) _database_code_depnum_ccdc_archive 'CCDC 849595' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 Co N2 O10' _chemical_formula_sum 'C26 H24 Co N2 O10' _chemical_formula_weight 583.40 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' Co Co 0.3494 0.9721 '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 13.090(5) _cell_length_b 7.694(3) _cell_length_c 12.632(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.422(6) _cell_angle_gamma 90.00 _cell_volume 1261.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 590 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 19.94 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8302 _exptl_absorpt_correction_T_max 0.8967 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6224 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.1120 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.19 _reflns_number_total 2270 _reflns_number_gt 1311 _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^)+(0.0413P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2270 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 Co1 Co 0.5000 0.5000 0.5000 0.0310(3) Uani 1 2 d S . . O1 O 0.4655(2) 0.3118(4) 0.3911(3) 0.0372(9) Uani 1 1 d . . . O2 O 0.3438(2) 0.2348(4) 0.2590(3) 0.0416(9) Uani 1 1 d . . . O3 O 0.5128(3) 0.6778(6) 0.3737(3) 0.0524(12) Uani 1 1 d . . . H3 H 0.549(4) 0.678(8) 0.340(5) 0.063 Uiso 1 1 d . . . O4 O 0.1794(2) 0.0841(5) 0.3421(3) 0.0419(9) Uani 1 1 d . . . O5 O 0.0889(3) 0.2481(5) 0.2165(3) 0.0584(12) Uani 1 1 d . . . N1 N 0.3302(3) 0.5276(5) 0.4671(3) 0.0309(10) Uani 1 1 d G . . C1 C 0.3731(4) 0.3055(6) 0.3452(4) 0.0314(12) Uani 1 1 d . . . C2 C 0.2923(3) 0.4059(6) 0.3981(4) 0.0277(11) Uani 1 1 d G . . C3 C 0.1874(3) 0.3825(6) 0.3673(4) 0.0294(12) Uani 1 1 d G . . C4 C 0.1470(4) 0.2330(7) 0.2980(4) 0.0371(13) Uani 1 1 d . . . C5 C 0.1612(4) -0.0650(6) 0.2747(4) 0.0556(16) Uani 1 1 d . . . H5A H 0.0908 -0.1015 0.2731 0.083 Uiso 1 1 calc R . . H5B H 0.2062 -0.1576 0.3021 0.083 Uiso 1 1 calc R . . H5C H 0.1742 -0.0361 0.2038 0.083 Uiso 1 1 calc R . . C6 C 0.1194(3) 0.4968(6) 0.4035(3) 0.0349(12) Uani 1 1 d G . . H6 H 0.0491 0.4859 0.3817 0.042 Uiso 1 1 calc R . . C7 C 0.1566(2) 0.6290(5) 0.4729(3) 0.0310(12) Uani 1 1 d G . . C12 C 0.2617(2) 0.6424(5) 0.5066(3) 0.0299(12) Uani 1 1 d G . . C8 C 0.0899(4) 0.7555(7) 0.5107(4) 0.0405(14) Uani 1 1 d . . . H8 H 0.0192 0.7485 0.4899 0.049 Uiso 1 1 calc R . . C9 C 0.1286(4) 0.8859(7) 0.5769(4) 0.0473(15) Uani 1 1 d . . . H9 H 0.0845 0.9680 0.6004 0.057 Uiso 1 1 calc R . . C10 C 0.2349(4) 0.8963(7) 0.6097(4) 0.0453(14) Uani 1 1 d . . . H10 H 0.2611 0.9858 0.6547 0.054 Uiso 1 1 calc R . . C11 C 0.3002(4) 0.7758(6) 0.5759(4) 0.0391(13) Uani 1 1 d . . . H11 H 0.3705 0.7824 0.5990 0.047 Uiso 1 1 calc R . . C13 C 0.4682(4) 0.8460(7) 0.3650(5) 0.0678(19) Uani 1 1 d . . . H13A H 0.3986 0.8401 0.3814 0.102 Uiso 1 1 calc R . . H13B H 0.4682 0.8885 0.2936 0.102 Uiso 1 1 calc R . . H13C H 0.5075 0.9231 0.4143 0.102 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0266(5) 0.0352(6) 0.0311(6) -0.0025(5) 0.0031(4) -0.0008(5) O1 0.0286(18) 0.044(2) 0.038(2) -0.0098(18) 0.0005(17) 0.0012(16) O2 0.0341(19) 0.054(2) 0.036(2) -0.0164(19) 0.0026(18) -0.0056(17) O3 0.056(3) 0.049(2) 0.057(3) 0.014(2) 0.026(2) 0.011(2) O4 0.049(2) 0.036(2) 0.040(2) -0.003(2) 0.0022(19) -0.0033(18) O5 0.058(3) 0.052(3) 0.057(3) -0.007(2) -0.024(2) 0.0045(19) N1 0.029(2) 0.039(3) 0.025(2) 0.001(2) 0.0047(18) -0.0026(19) C1 0.031(3) 0.027(3) 0.037(3) -0.002(3) 0.008(3) -0.003(2) C2 0.030(3) 0.031(3) 0.023(3) -0.002(2) 0.003(2) 0.001(2) C3 0.023(3) 0.033(3) 0.031(3) 0.004(2) -0.001(2) -0.003(2) C4 0.029(3) 0.041(3) 0.041(3) -0.001(3) 0.005(3) -0.003(3) C5 0.072(4) 0.041(4) 0.054(4) -0.001(3) 0.009(3) -0.005(3) C6 0.019(2) 0.046(3) 0.039(3) 0.008(3) 0.000(2) -0.009(3) C7 0.027(3) 0.035(3) 0.032(3) 0.001(2) 0.008(2) 0.004(2) C12 0.026(3) 0.035(3) 0.030(3) 0.001(2) 0.008(2) 0.001(2) C8 0.033(3) 0.046(3) 0.043(3) 0.005(3) 0.008(3) 0.004(3) C9 0.047(3) 0.041(4) 0.056(4) -0.004(3) 0.012(3) 0.013(3) C10 0.044(3) 0.042(3) 0.050(4) -0.014(3) 0.007(3) 0.002(3) C11 0.035(3) 0.046(4) 0.036(3) -0.006(3) 0.003(3) 0.000(3) C13 0.088(5) 0.051(4) 0.070(5) 0.015(4) 0.027(4) 0.024(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.008(3) 3_666 ? Co1 O1 2.008(3) . ? Co1 O3 2.125(4) 3_666 ? Co1 O3 2.125(4) . ? Co1 N1 2.218(4) . ? Co1 N1 2.218(4) 3_666 ? O1 C1 1.273(5) . ? O2 C1 1.234(5) . ? O3 C13 1.418(6) . ? O3 H3 0.68(5) . ? O4 C4 1.320(5) . ? O4 C5 1.430(5) . ? O5 C4 1.204(5) . ? N1 C2 1.330(5) . ? N1 C12 1.397(5) . ? C1 C2 1.532(6) . ? C2 C3 1.3900 . ? C3 C6 1.371(6) . ? C3 C4 1.500(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.3900 . ? C6 H6 0.9300 . ? C7 C12 1.3900 . ? C7 C8 1.430(5) . ? C12 C11 1.399(6) . ? C8 C9 1.361(6) . ? C8 H8 0.9300 . ? C9 C10 1.402(6) . ? C9 H9 0.9300 . ? C10 C11 1.367(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 O1 Co1 O1 180.0 3_666 . ? O1 Co1 O3 89.00(16) 3_666 3_666 ? O1 Co1 O3 91.00(16) . 3_666 ? O1 Co1 O3 91.00(16) 3_666 . ? O1 Co1 O3 89.00(16) . . ? O3 Co1 O3 180.0 3_666 . ? O1 Co1 N1 100.99(13) 3_666 . ? O1 Co1 N1 79.01(13) . . ? O3 Co1 N1 91.62(14) 3_666 . ? O3 Co1 N1 88.38(14) . . ? O1 Co1 N1 79.01(13) 3_666 3_666 ? O1 Co1 N1 100.99(13) . 3_666 ? O3 Co1 N1 88.38(14) 3_666 3_666 ? O3 Co1 N1 91.62(14) . 3_666 ? N1 Co1 N1 180.0 . 3_666 ? C1 O1 Co1 117.1(3) . . ? C13 O3 Co1 125.0(3) . . ? C13 O3 H3 105(6) . . ? Co1 O3 H3 127(5) . . ? C4 O4 C5 115.2(4) . . ? C2 N1 C12 118.5(3) . . ? C2 N1 Co1 109.6(3) . . ? C12 N1 Co1 131.9(3) . . ? O2 C1 O1 126.0(5) . . ? O2 C1 C2 117.0(4) . . ? O1 C1 C2 116.8(4) . . ? N1 C2 C3 123.1(4) . . ? N1 C2 C1 114.9(3) . . ? C3 C2 C1 121.7(4) . . ? C2 C3 C6 118.9(4) . . ? C2 C3 C4 121.6(4) . . ? C6 C3 C4 119.4(3) . . ? O5 C4 O4 125.3(5) . . ? O5 C4 C3 124.1(5) . . ? O4 C4 C3 110.4(4) . . ? O4 C5 H5A 109.5 . . ? O4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C3 119.4(3) . . ? C7 C6 H6 120.3 . . ? C3 C6 H6 120.3 . . ? C12 C7 C6 120.0 . . ? C12 C7 C8 118.0(3) . . ? C6 C7 C8 122.0(3) . . ? C11 C12 C7 120.5(4) . . ? C11 C12 N1 119.4(3) . . ? C7 C12 N1 120.0(3) . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.0(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.4(5) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.2(5) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O1 Co1 O1 C1 57(100) 3_666 . . . ? O3 Co1 O1 C1 99.6(3) 3_666 . . . ? O3 Co1 O1 C1 -80.4(3) . . . . ? N1 Co1 O1 C1 8.1(3) . . . . ? N1 Co1 O1 C1 -171.9(3) 3_666 . . . ? O1 Co1 O3 C13 -46.7(4) 3_666 . . . ? O1 Co1 O3 C13 133.3(4) . . . . ? O3 Co1 O3 C13 92(100) 3_666 . . . ? N1 Co1 O3 C13 54.2(4) . . . . ? N1 Co1 O3 C13 -125.8(4) 3_666 . . . ? O1 Co1 N1 C2 -177.5(3) 3_666 . . . ? O1 Co1 N1 C2 2.5(3) . . . . ? O3 Co1 N1 C2 -88.2(3) 3_666 . . . ? O3 Co1 N1 C2 91.8(3) . . . . ? N1 Co1 N1 C2 -48(100) 3_666 . . . ? O1 Co1 N1 C12 0.9(4) 3_666 . . . ? O1 Co1 N1 C12 -179.1(4) . . . . ? O3 Co1 N1 C12 90.2(4) 3_666 . . . ? O3 Co1 N1 C12 -89.8(4) . . . . ? N1 Co1 N1 C12 130(100) 3_666 . . . ? Co1 O1 C1 O2 158.9(4) . . . . ? Co1 O1 C1 C2 -16.6(5) . . . . ? C12 N1 C2 C3 -3.1(7) . . . . ? Co1 N1 C2 C3 175.6(4) . . . . ? C12 N1 C2 C1 170.5(4) . . . . ? Co1 N1 C2 C1 -10.9(5) . . . . ? O2 C1 C2 N1 -157.1(4) . . . . ? O1 C1 C2 N1 18.8(6) . . . . ? O2 C1 C2 C3 16.5(7) . . . . ? O1 C1 C2 C3 -167.6(4) . . . . ? N1 C2 C3 C6 4.6(7) . . . . ? C1 C2 C3 C6 -168.5(4) . . . . ? N1 C2 C3 C4 -173.8(4) . . . . ? C1 C2 C3 C4 13.1(7) . . . . ? C5 O4 C4 O5 14.3(7) . . . . ? C5 O4 C4 C3 -169.3(4) . . . . ? C2 C3 C4 O5 -127.1(5) . . . . ? C6 C3 C4 O5 54.5(7) . . . . ? C2 C3 C4 O4 56.5(6) . . . . ? C6 C3 C4 O4 -121.9(5) . . . . ? C2 C3 C6 C7 -2.4(7) . . . . ? C4 C3 C6 C7 176.1(4) . . . . ? C3 C6 C7 C12 -1.2(7) . . . . ? C3 C6 C7 C8 178.0(4) . . . . ? C6 C7 C12 C11 179.5(4) . . . . ? C8 C7 C12 C11 0.2(7) . . . . ? C6 C7 C12 N1 2.8(7) . . . . ? C8 C7 C12 N1 -176.5(4) . . . . ? C2 N1 C12 C11 -177.4(4) . . . . ? Co1 N1 C12 C11 4.3(6) . . . . ? C2 N1 C12 C7 -0.7(6) . . . . ? Co1 N1 C12 C7 -179.0(3) . . . . ? C12 C7 C8 C9 0.7(7) . . . . ? C6 C7 C8 C9 -178.6(5) . . . . ? C7 C8 C9 C10 -0.7(8) . . . . ? C8 C9 C10 C11 -0.2(8) . . . . ? C9 C10 C11 C12 1.1(8) . . . . ? C7 C12 C11 C10 -1.1(7) . . . . ? N1 C12 C11 C10 175.6(5) . . . . ? 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 H3 O2 0.68(5) 2.04(6) 2.708(5) 168(7) 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.385 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.082 ############# END ################## data_849594(2) _database_code_depnum_ccdc_archive 'CCDC 849596' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 Co N2 O4' _chemical_formula_sum 'C20 H12 Co N2 O4' _chemical_formula_weight 403.25 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.867(4) _cell_length_b 8.0358(12) _cell_length_c 15.211(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.151(2) _cell_angle_gamma 90.00 _cell_volume 3219.7(8) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1425 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 23.60 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7634 _exptl_absorpt_correction_T_max 0.8527 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7971 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2890 _reflns_number_gt 2195 _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^)+(0.0315P)^2^+3.6825P] 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 2890 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Co1 Co 0.374264(15) 0.62245(5) 0.56815(3) 0.02471(15) Uani 1 1 d . . . O1 O 0.35589(9) 0.4142(3) 0.21760(16) 0.0423(6) Uani 1 1 d . . . O2 O 0.42295(8) 0.4764(3) 0.18995(14) 0.0370(6) Uani 1 1 d . . . O3 O 0.33421(9) 0.8224(3) 0.52169(17) 0.0392(6) Uani 1 1 d . . . O4 O 0.39685(9) 0.9717(3) 0.62729(17) 0.0474(7) Uani 1 1 d . . . N1 N 0.41896(9) 0.6275(3) 0.48974(16) 0.0249(6) Uani 1 1 d . . . N2 N 0.32800(9) 1.4148(3) 0.50656(17) 0.0231(6) Uani 1 1 d . . . C1 C 0.39993(11) 0.5591(4) 0.4030(2) 0.0270(7) Uani 1 1 d . . . H1 H 0.3687 0.5058 0.3833 0.032 Uiso 1 1 calc R . . C2 C 0.42332(12) 0.5611(4) 0.3390(2) 0.0260(7) Uani 1 1 d . . . C3 C 0.39853(13) 0.4769(4) 0.2434(2) 0.0316(8) Uani 1 1 d . . . C4 C 0.46869(12) 0.6421(4) 0.3666(2) 0.0302(8) Uani 1 1 d . . . H4 H 0.4850 0.6466 0.3252 0.036 Uiso 1 1 calc R . . C5 C 0.49079(11) 0.7190(4) 0.4577(2) 0.0277(7) Uani 1 1 d . . . C6 C 0.53744(12) 0.8058(4) 0.4898(2) 0.0386(9) Uani 1 1 d . . . H6 H 0.5541 0.8179 0.4492 0.046 Uiso 1 1 calc R . . C7 C 0.55788(13) 0.8715(4) 0.5798(2) 0.0399(9) Uani 1 1 d . . . H7 H 0.5887 0.9277 0.6005 0.048 Uiso 1 1 calc R . . C8 C 0.53356(12) 0.8561(4) 0.6415(2) 0.0357(8) Uani 1 1 d . . . H8 H 0.5484 0.9009 0.7032 0.043 Uiso 1 1 calc R . . C9 C 0.48800(12) 0.7757(4) 0.6124(2) 0.0299(7) Uani 1 1 d . . . H9 H 0.4719 0.7665 0.6542 0.036 Uiso 1 1 calc R . . C10 C 0.46540(11) 0.7069(4) 0.5194(2) 0.0258(7) Uani 1 1 d . . . C11 C 0.34819(11) 1.2697(4) 0.5438(2) 0.0259(7) Uani 1 1 d . . . H11 H 0.3787 1.2717 0.5982 0.031 Uiso 1 1 calc R . . C12 C 0.32760(11) 1.1133(4) 0.5086(2) 0.0234(7) Uani 1 1 d . . . C13 C 0.35557(13) 0.9600(4) 0.5575(2) 0.0304(7) Uani 1 1 d . . . C14 C 0.28288(11) 1.1094(4) 0.4288(2) 0.0279(7) Uani 1 1 d . . . H14 H 0.2682 1.0077 0.4031 0.034 Uiso 1 1 calc R . . C15 C 0.25883(11) 1.2579(4) 0.3850(2) 0.0261(7) Uani 1 1 d . . . C16 C 0.21231(12) 1.2600(5) 0.3035(2) 0.0371(8) Uani 1 1 d . . . H16 H 0.1969 1.1604 0.2756 0.045 Uiso 1 1 calc R . . C17 C 0.18989(13) 1.4067(5) 0.2655(2) 0.0417(9) Uani 1 1 d . . . H17 H 0.1593 1.4067 0.2111 0.050 Uiso 1 1 calc R . . C18 C 0.21211(13) 1.5583(5) 0.3070(2) 0.0407(9) Uani 1 1 d . . . H18 H 0.1959 1.6579 0.2809 0.049 Uiso 1 1 calc R . . C19 C 0.25747(12) 1.5606(4) 0.3857(2) 0.0325(8) Uani 1 1 d . . . H19 H 0.2722 1.6617 0.4125 0.039 Uiso 1 1 calc R . . C20 C 0.28191(11) 1.4114(4) 0.4261(2) 0.0246(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0314(3) 0.0190(2) 0.0234(2) 0.00100(19) 0.01088(18) -0.00044(19) O1 0.0448(15) 0.0405(16) 0.0339(13) -0.0088(11) 0.0084(11) -0.0091(12) O2 0.0435(14) 0.0431(15) 0.0208(11) -0.0044(11) 0.0094(10) 0.0089(12) O3 0.0512(15) 0.0166(13) 0.0475(14) 0.0024(11) 0.0180(12) 0.0037(11) O4 0.0413(15) 0.0384(16) 0.0484(15) 0.0105(12) 0.0040(13) 0.0098(12) N1 0.0320(14) 0.0231(14) 0.0182(13) -0.0015(11) 0.0091(11) -0.0029(12) N2 0.0273(14) 0.0185(15) 0.0234(13) 0.0012(11) 0.0102(11) 0.0005(11) C1 0.0283(17) 0.0219(17) 0.0271(17) 0.0018(14) 0.0077(14) -0.0015(13) C2 0.0349(18) 0.0232(17) 0.0199(15) -0.0005(13) 0.0111(14) 0.0045(14) C3 0.044(2) 0.0255(19) 0.0200(16) 0.0009(14) 0.0079(16) 0.0100(16) C4 0.0336(18) 0.034(2) 0.0252(16) 0.0025(15) 0.0149(14) 0.0044(15) C5 0.0284(17) 0.0265(18) 0.0273(17) 0.0028(14) 0.0104(14) 0.0027(14) C6 0.034(2) 0.040(2) 0.044(2) -0.0022(17) 0.0188(17) -0.0045(16) C7 0.0330(19) 0.036(2) 0.043(2) -0.0059(18) 0.0084(16) -0.0110(16) C8 0.038(2) 0.031(2) 0.0274(17) -0.0050(15) 0.0027(15) -0.0032(16) C9 0.0358(19) 0.0288(19) 0.0244(17) -0.0017(14) 0.0117(14) 0.0007(15) C10 0.0296(17) 0.0197(17) 0.0261(17) 0.0023(14) 0.0093(14) 0.0013(14) C11 0.0252(17) 0.0252(18) 0.0253(16) 0.0016(14) 0.0081(13) 0.0029(14) C12 0.0290(17) 0.0182(17) 0.0241(16) 0.0010(13) 0.0120(14) 0.0008(13) C13 0.040(2) 0.0233(19) 0.0330(18) 0.0073(15) 0.0201(17) 0.0075(16) C14 0.0345(18) 0.0189(17) 0.0301(17) -0.0038(14) 0.0129(15) -0.0043(14) C15 0.0273(17) 0.0251(18) 0.0254(16) -0.0002(14) 0.0103(14) -0.0004(14) C16 0.0336(19) 0.040(2) 0.0308(19) -0.0022(16) 0.0065(15) -0.0042(16) C17 0.0296(19) 0.050(3) 0.0332(19) 0.0077(17) -0.0002(16) 0.0056(17) C18 0.041(2) 0.036(2) 0.042(2) 0.0137(17) 0.0136(18) 0.0126(17) C19 0.0382(19) 0.0227(18) 0.0344(19) 0.0034(15) 0.0125(16) 0.0009(15) C20 0.0302(17) 0.0215(18) 0.0239(16) 0.0003(13) 0.0128(14) -0.0005(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 1.936(2) . ? Co1 O2 1.977(2) 6_566 ? Co1 N1 2.085(2) . ? Co1 N2 2.103(2) 1_545 ? O1 C3 1.236(4) . ? O2 C3 1.275(4) . ? O2 Co1 1.977(2) 6_565 ? O3 C13 1.275(4) . ? O4 C13 1.233(4) . ? N1 C1 1.324(4) . ? N1 C10 1.383(4) . ? N2 C11 1.323(4) . ? N2 C20 1.392(4) . ? N2 Co1 2.103(2) 1_565 ? C1 C2 1.394(4) . ? C1 H1 0.9300 . ? C2 C4 1.366(4) . ? C2 C3 1.495(4) . ? C4 C5 1.409(4) . ? C4 H4 0.9300 . ? C5 C10 1.410(4) . ? C5 C6 1.414(4) . ? C6 C7 1.356(5) . ? C6 H6 0.9300 . ? C7 C8 1.388(5) . ? C7 H7 0.9300 . ? C8 C9 1.366(4) . ? C8 H8 0.9300 . ? C9 C10 1.407(4) . ? C9 H9 0.9300 . ? C11 C12 1.400(4) . ? C11 H11 0.9300 . ? C12 C14 1.363(4) . ? C12 C13 1.494(4) . ? C14 C15 1.404(4) . ? C14 H14 0.9300 . ? C15 C16 1.407(4) . ? C15 C20 1.419(4) . ? C16 C17 1.355(5) . ? C16 H16 0.9300 . ? C17 C18 1.402(5) . ? C17 H17 0.9300 . ? C18 C19 1.365(4) . ? C18 H18 0.9300 . ? C19 C20 1.400(4) . ? C19 H19 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 Co1 O2 139.90(10) . 6_566 ? O3 Co1 N1 101.08(10) . . ? O2 Co1 N1 100.07(9) 6_566 . ? O3 Co1 N2 108.68(10) . 1_545 ? O2 Co1 N2 100.19(9) 6_566 1_545 ? N1 Co1 N2 100.91(9) . 1_545 ? C3 O2 Co1 103.4(2) . 6_565 ? C13 O3 Co1 116.8(2) . . ? C1 N1 C10 117.9(3) . . ? C1 N1 Co1 117.4(2) . . ? C10 N1 Co1 124.51(19) . . ? C11 N2 C20 117.0(3) . . ? C11 N2 Co1 114.86(19) . 1_565 ? C20 N2 Co1 127.72(19) . 1_565 ? N1 C1 C2 124.7(3) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? C4 C2 C1 117.9(3) . . ? C4 C2 C3 122.2(3) . . ? C1 C2 C3 119.9(3) . . ? O1 C3 O2 122.4(3) . . ? O1 C3 C2 120.7(3) . . ? O2 C3 C2 116.9(3) . . ? C2 C4 C5 120.2(3) . . ? C2 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C10 118.3(3) . . ? C4 C5 C6 122.7(3) . . ? C10 C5 C6 119.0(3) . . ? C7 C6 C5 120.0(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? N1 C10 C9 119.9(3) . . ? N1 C10 C5 120.9(3) . . ? C9 C10 C5 119.3(3) . . ? N2 C11 C12 125.7(3) . . ? N2 C11 H11 117.2 . . ? C12 C11 H11 117.2 . . ? C14 C12 C11 117.4(3) . . ? C14 C12 C13 123.1(3) . . ? C11 C12 C13 119.4(3) . . ? O4 C13 O3 124.2(3) . . ? O4 C13 C12 120.1(3) . . ? O3 C13 C12 115.7(3) . . ? C12 C14 C15 120.5(3) . . ? C12 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 122.5(3) . . ? C14 C15 C20 118.5(3) . . ? C16 C15 C20 119.0(3) . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.9(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.3(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? N2 C20 C19 119.9(3) . . ? N2 C20 C15 120.8(3) . . ? C19 C20 C15 119.3(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 O2 Co1 O3 C13 41.3(3) 6_566 . . . ? N1 Co1 O3 C13 -79.3(2) . . . . ? N2 Co1 O3 C13 175.1(2) 1_545 . . . ? O3 Co1 N1 C1 -86.7(2) . . . . ? O2 Co1 N1 C1 127.6(2) 6_566 . . . ? N2 Co1 N1 C1 25.0(2) 1_545 . . . ? O3 Co1 N1 C10 88.7(2) . . . . ? O2 Co1 N1 C10 -57.0(2) 6_566 . . . ? N2 Co1 N1 C10 -159.6(2) 1_545 . . . ? C10 N1 C1 C2 0.0(4) . . . . ? Co1 N1 C1 C2 175.7(2) . . . . ? N1 C1 C2 C4 -1.4(5) . . . . ? N1 C1 C2 C3 178.9(3) . . . . ? Co1 O2 C3 O1 4.6(4) 6_565 . . . ? Co1 O2 C3 C2 -173.9(2) 6_565 . . . ? C4 C2 C3 O1 -175.0(3) . . . . ? C1 C2 C3 O1 4.6(5) . . . . ? C4 C2 C3 O2 3.5(5) . . . . ? C1 C2 C3 O2 -176.8(3) . . . . ? C1 C2 C4 C5 0.7(4) . . . . ? C3 C2 C4 C5 -179.6(3) . . . . ? C2 C4 C5 C10 1.2(5) . . . . ? C2 C4 C5 C6 -179.5(3) . . . . ? C4 C5 C6 C7 -177.3(3) . . . . ? C10 C5 C6 C7 2.0(5) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C6 C7 C8 C9 -0.7(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C1 N1 C10 C9 -177.5(3) . . . . ? Co1 N1 C10 C9 7.1(4) . . . . ? C1 N1 C10 C5 2.0(4) . . . . ? Co1 N1 C10 C5 -173.4(2) . . . . ? C8 C9 C10 N1 -179.2(3) . . . . ? C8 C9 C10 C5 1.3(5) . . . . ? C4 C5 C10 N1 -2.6(4) . . . . ? C6 C5 C10 N1 178.0(3) . . . . ? C4 C5 C10 C9 176.9(3) . . . . ? C6 C5 C10 C9 -2.4(4) . . . . ? C20 N2 C11 C12 1.0(4) . . . . ? Co1 N2 C11 C12 -172.5(2) 1_565 . . . ? N2 C11 C12 C14 0.1(4) . . . . ? N2 C11 C12 C13 178.7(3) . . . . ? Co1 O3 C13 O4 -9.7(4) . . . . ? Co1 O3 C13 C12 169.51(19) . . . . ? C14 C12 C13 O4 177.2(3) . . . . ? C11 C12 C13 O4 -1.3(4) . . . . ? C14 C12 C13 O3 -2.0(4) . . . . ? C11 C12 C13 O3 179.5(3) . . . . ? C11 C12 C14 C15 -0.4(4) . . . . ? C13 C12 C14 C15 -178.9(3) . . . . ? C12 C14 C15 C16 -179.0(3) . . . . ? C12 C14 C15 C20 -0.4(4) . . . . ? C14 C15 C16 C17 178.1(3) . . . . ? C20 C15 C16 C17 -0.5(5) . . . . ? C15 C16 C17 C18 -0.8(5) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C11 N2 C20 C19 177.2(3) . . . . ? Co1 N2 C20 C19 -10.3(4) 1_565 . . . ? C11 N2 C20 C15 -1.8(4) . . . . ? Co1 N2 C20 C15 170.7(2) 1_565 . . . ? C18 C19 C20 N2 -179.6(3) . . . . ? C18 C19 C20 C15 -0.6(5) . . . . ? C14 C15 C20 N2 1.5(4) . . . . ? C16 C15 C20 N2 -179.8(3) . . . . ? C14 C15 C20 C19 -177.5(3) . . . . ? C16 C15 C20 C19 1.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.352 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.070 ################## END ############### data_849595(4) _database_code_depnum_ccdc_archive 'CCDC 849597' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 N2 O10 Zn' _chemical_formula_sum 'C22 H16 N2 O10 Zn' _chemical_formula_weight 533.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4062(17) _cell_length_b 9.136(2) _cell_length_c 9.415(3) _cell_angle_alpha 110.466(4) _cell_angle_beta 98.320(4) _cell_angle_gamma 111.664(3) _cell_volume 526.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 631 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272.0 _exptl_absorpt_coefficient_mu 1.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.831 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 2731 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.20 _reflns_number_total 1899 _reflns_number_gt 1581 _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 'SHELXS-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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. The water H atoms were located and isotropically refined, with the O-H and H...H for water molecule distances restrained to 0.85(1) and 1.43(2)\%A, respectively. U~iso~ values were set equal to 1.5U~eq~(parent atom) for water H atoms. ; _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^)+(0.0492P)^2^+1.9264P] 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 1861 _refine_ls_number_parameters 165 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 0.0000 0.5000 0.0363(3) Uani 1 2 d S . . O2 O 0.0983(5) 0.2570(4) 0.6464(4) 0.0325(8) Uani 1 1 d . . . O1 O 0.1960(6) 0.5253(4) 0.6762(4) 0.0432(10) Uani 1 1 d . . . O4 O 0.3057(6) 0.7025(4) 0.5402(4) 0.0422(9) Uani 1 1 d . . . H4 H 0.2633 0.6359 0.5837 0.063 Uiso 1 1 d R . . O5 O 0.3837(6) 0.6805(4) 0.3209(5) 0.0462(10) Uani 1 1 d . . . O3 O -0.2783(5) -0.0151(4) 0.3924(4) 0.0320(8) Uani 1 1 d D . . H3A H -0.3731 -0.1031 0.3847 0.048 Uiso 1 1 calc RD . . N1 N 0.1558(5) 0.1433(4) 0.3707(4) 0.0220(8) Uani 1 1 d . . . C1 C 0.1601(7) 0.3690(6) 0.5961(5) 0.0273(10) Uani 1 1 d . . . C4 C 0.3223(7) 0.6138(6) 0.4060(6) 0.0313(11) Uani 1 1 d . . . C3 C 0.2644(7) 0.4190(5) 0.3524(5) 0.0240(10) Uani 1 1 d . . . C2 C 0.1940(7) 0.3117(5) 0.4325(5) 0.0227(9) Uani 1 1 d . . . C11 C 0.1915(7) 0.0699(5) 0.2306(5) 0.0234(9) Uani 1 1 d . . . C10 C 0.1699(8) -0.1037(6) 0.1731(6) 0.0302(11) Uani 1 1 d . . . H10 H 0.1345 -0.1673 0.2317 0.036 Uiso 1 1 calc R . . C9 C 0.2015(8) -0.1766(6) 0.0313(6) 0.0343(11) Uani 1 1 d . . . H9 H 0.1874 -0.2901 -0.0058 0.041 Uiso 1 1 calc R . . C8 C 0.2549(8) -0.0836(7) -0.0597(6) 0.0348(12) Uani 1 1 d . . . H8 H 0.2725 -0.1369 -0.1572 0.042 Uiso 1 1 calc R . . C7 C 0.2812(7) 0.0842(6) -0.0057(6) 0.0315(11) Uani 1 1 d . . . H7 H 0.3171 0.1455 -0.0662 0.038 Uiso 1 1 calc R . . C6 C 0.2540(7) 0.1656(6) 0.1420(5) 0.0264(10) Uani 1 1 d . . . C5 C 0.2878(7) 0.3406(6) 0.2079(6) 0.0285(10) Uani 1 1 d . . . H5 H 0.3276 0.4058 0.1512 0.034 Uiso 1 1 calc R . . H3B H -0.272(8) 0.085(3) 0.414(7) 0.06(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0486(6) 0.0247(5) 0.0367(5) 0.0137(4) 0.0173(4) 0.0161(4) O2 0.051(2) 0.0172(15) 0.0303(18) 0.0087(14) 0.0228(16) 0.0140(15) O1 0.071(3) 0.0168(17) 0.040(2) 0.0078(15) 0.029(2) 0.0190(18) O4 0.063(3) 0.0186(17) 0.046(2) 0.0146(16) 0.0175(19) 0.0185(17) O5 0.062(3) 0.0226(18) 0.054(2) 0.0250(18) 0.019(2) 0.0111(17) O3 0.0363(19) 0.0191(17) 0.040(2) 0.0152(16) 0.0113(16) 0.0102(15) N1 0.027(2) 0.0158(17) 0.0245(19) 0.0095(15) 0.0095(16) 0.0100(16) C1 0.031(3) 0.017(2) 0.029(2) 0.0056(19) 0.010(2) 0.010(2) C4 0.029(3) 0.019(2) 0.041(3) 0.013(2) 0.004(2) 0.008(2) C3 0.024(2) 0.017(2) 0.032(2) 0.0125(19) 0.0070(19) 0.0084(18) C2 0.027(2) 0.016(2) 0.025(2) 0.0083(18) 0.0089(19) 0.0096(19) C11 0.023(2) 0.020(2) 0.025(2) 0.0078(19) 0.0079(19) 0.0092(19) C10 0.040(3) 0.024(2) 0.035(3) 0.015(2) 0.020(2) 0.018(2) C9 0.038(3) 0.024(2) 0.036(3) 0.008(2) 0.013(2) 0.016(2) C8 0.039(3) 0.037(3) 0.025(2) 0.008(2) 0.014(2) 0.018(2) C7 0.032(3) 0.038(3) 0.030(3) 0.019(2) 0.014(2) 0.016(2) C6 0.024(2) 0.029(2) 0.029(2) 0.015(2) 0.0087(19) 0.011(2) C5 0.030(3) 0.024(2) 0.033(3) 0.017(2) 0.010(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.031(3) 2_556 ? Zn1 O2 2.031(3) . ? Zn1 O3 2.093(3) 2_556 ? Zn1 O3 2.093(3) . ? Zn1 N1 2.221(3) 2_556 ? Zn1 N1 2.221(3) . ? O2 C1 1.240(5) . ? O1 C1 1.260(5) . ? O4 C4 1.293(6) . ? O4 H4 0.8406 . ? O5 C4 1.209(6) . ? O3 H3A 0.8200 . ? O3 H3B 0.849(18) . ? N1 C2 1.338(5) . ? N1 C11 1.368(6) . ? C1 C2 1.534(6) . ? C4 C3 1.533(6) . ? C3 C5 1.368(6) . ? C3 C2 1.434(6) . ? C11 C6 1.414(6) . ? C11 C10 1.421(6) . ? C10 C9 1.365(7) . ? C10 H10 0.9300 . ? C9 C8 1.403(7) . ? C9 H9 0.9300 . ? C8 C7 1.362(7) . ? C8 H8 0.9300 . ? C7 C6 1.412(7) . ? C7 H7 0.9300 . ? C6 C5 1.404(6) . ? C5 H5 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 180.0(3) 2_556 . ? O2 Zn1 O3 89.76(14) 2_556 2_556 ? O2 Zn1 O3 90.24(14) . 2_556 ? O2 Zn1 O3 90.24(14) 2_556 . ? O2 Zn1 O3 89.76(14) . . ? O3 Zn1 O3 180.00(9) 2_556 . ? O2 Zn1 N1 75.24(13) 2_556 2_556 ? O2 Zn1 N1 104.76(13) . 2_556 ? O3 Zn1 N1 90.74(13) 2_556 2_556 ? O3 Zn1 N1 89.26(13) . 2_556 ? O2 Zn1 N1 104.76(13) 2_556 . ? O2 Zn1 N1 75.24(13) . . ? O3 Zn1 N1 89.26(13) 2_556 . ? O3 Zn1 N1 90.74(13) . . ? N1 Zn1 N1 180.0 2_556 . ? C1 O2 Zn1 120.1(3) . . ? C4 O4 H4 108.7 . . ? Zn1 O3 H3A 109.5 . . ? Zn1 O3 H3B 112(4) . . ? H3A O3 H3B 128.6 . . ? C2 N1 C11 120.4(4) . . ? C2 N1 Zn1 113.4(3) . . ? C11 N1 Zn1 125.7(3) . . ? O2 C1 O1 121.6(4) . . ? O2 C1 C2 117.8(4) . . ? O1 C1 C2 120.6(4) . . ? O5 C4 O4 121.8(4) . . ? O5 C4 C3 118.6(4) . . ? O4 C4 C3 119.6(4) . . ? C5 C3 C2 116.9(4) . . ? C5 C3 C4 113.7(4) . . ? C2 C3 C4 129.4(4) . . ? N1 C2 C3 121.8(4) . . ? N1 C2 C1 111.2(4) . . ? C3 C2 C1 127.0(4) . . ? N1 C11 C6 120.9(4) . . ? N1 C11 C10 120.4(4) . . ? C6 C11 C10 118.7(4) . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C9 C8 121.3(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C5 C6 C7 123.0(4) . . ? C5 C6 C11 117.2(4) . . ? C7 C6 C11 119.8(4) . . ? C3 C5 C6 122.5(4) . . ? C3 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.384 _refine_diff_density_min -0.699 _refine_diff_density_rms 0.097 ############### END ################### data_849596(6) _database_code_depnum_ccdc_archive 'CCDC 849598' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 O10 Zn' _chemical_formula_sum 'C26 H24 N2 O10 Zn' _chemical_formula_weight 589.84 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 12.984(8) _cell_length_b 7.731(5) _cell_length_c 12.571(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.320(7) _cell_angle_gamma 90.00 _cell_volume 1251.7(13) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1297 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 21.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7729 _exptl_absorpt_correction_T_max 0.8849 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6064 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0852 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.19 _reflns_number_total 2248 _reflns_number_gt 1608 _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^)+(0.1240P)^2^+0.9989P] 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 2248 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1046 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C12 C 0.73611(13) 0.1427(2) -0.00780(13) 0.0269(9) Uani 1 1 d G . . C7 C 0.84218(13) 0.1279(3) 0.02448(16) 0.0298(10) Uani 1 1 d G . . C6 C 0.87969(13) -0.0024(3) 0.09520(19) 0.0312(10) Uani 1 1 d G . . H6 H 0.9507 -0.0124 0.1168 0.037 Uiso 1 1 calc R . . C3 C 0.81114(18) -0.1179(3) 0.13363(17) 0.0297(10) Uani 1 1 d G . . C2 C 0.70507(17) -0.1031(3) 0.10134(17) 0.0263(10) Uani 1 1 d G . . N1 N 0.66755(12) 0.0273(3) 0.03063(15) 0.0241(8) Uani 1 1 d G . . Zn1 Zn 0.5000 0.0000 0.0000 0.03136(19) Uani 1 2 d S . . C8 C 0.9101(3) 0.2553(6) -0.0105(3) 0.0354(11) Uani 1 1 d . . . H8 H 0.9810 0.2492 0.0123 0.042 Uiso 1 1 calc R . . C11 C 0.6980(3) 0.2748(6) -0.0782(3) 0.0356(11) Uani 1 1 d . . . H11 H 0.6274 0.2818 -0.1024 0.043 Uiso 1 1 calc R . . C10 C 0.7649(3) 0.3928(6) -0.1109(3) 0.0381(11) Uani 1 1 d . . . H10 H 0.7390 0.4810 -0.1571 0.046 Uiso 1 1 calc R . . C9 C 0.8722(3) 0.3852(6) -0.0768(3) 0.0383(11) Uani 1 1 d . . . H9 H 0.9165 0.4681 -0.0994 0.046 Uiso 1 1 calc R . . O5 O 0.8216(2) -0.4167(4) 0.1565(2) 0.0376(8) Uani 1 1 d . . . C4 C 0.8527(3) -0.2670(6) 0.2015(3) 0.0314(10) Uani 1 1 d . . . O4 O 0.9091(2) -0.2526(4) 0.2842(2) 0.0492(9) Uani 1 1 d . . . O2 O 0.65516(19) -0.2682(4) 0.2390(2) 0.0359(8) Uani 1 1 d . . . C1 C 0.6251(3) -0.1960(5) 0.1539(3) 0.0263(9) Uani 1 1 d . . . O3 O 0.4885(2) 0.1739(4) 0.1264(2) 0.0420(8) Uani 1 1 d . . . H3 H 0.4555 0.1363 0.1837 0.050 Uiso 1 1 calc R . . C13 C 0.5275(4) 0.3428(6) 0.1297(4) 0.0568(15) Uani 1 1 d . . . H13A H 0.5811 0.3512 0.0839 0.085 Uiso 1 1 calc R . . H13B H 0.5557 0.3711 0.2019 0.085 Uiso 1 1 calc R . . H13C H 0.4725 0.4219 0.1054 0.085 Uiso 1 1 calc R . . O1 O 0.53212(19) -0.1866(4) 0.1095(2) 0.0328(7) Uani 1 1 d . . . C5 C 0.8390(4) -0.5650(7) 0.2239(4) 0.0470(11) Uiso 1 1 d . . . H5A H 0.9087 -0.6056 0.2228 0.070 Uiso 1 1 calc R . . H5B H 0.7909 -0.6545 0.1984 0.070 Uiso 1 1 calc R . . H5C H 0.8291 -0.5345 0.2960 0.070 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 C12 0.0320(18) 0.024(2) 0.0255(18) -0.0023(17) 0.0075(15) -0.0018(16) C7 0.0329(18) 0.033(2) 0.0254(19) -0.0027(17) 0.0105(15) -0.0007(18) C6 0.0240(18) 0.042(3) 0.028(2) -0.0022(19) 0.0063(15) -0.0017(17) C3 0.0343(19) 0.031(2) 0.0233(18) -0.0008(18) 0.0013(15) 0.0051(18) C2 0.0263(17) 0.034(2) 0.0197(17) -0.0006(16) 0.0065(14) 0.0016(17) N1 0.0270(15) 0.0251(18) 0.0202(15) 0.0035(13) 0.0036(12) -0.0005(13) Zn1 0.0304(3) 0.0344(4) 0.0294(3) 0.0031(3) 0.0042(3) 0.0008(3) C8 0.0286(18) 0.046(3) 0.033(2) -0.004(2) 0.0070(16) -0.0088(18) C11 0.0317(19) 0.041(3) 0.034(2) 0.009(2) 0.0044(16) 0.0004(19) C10 0.046(2) 0.031(2) 0.037(2) 0.011(2) 0.0065(18) -0.002(2) C9 0.048(2) 0.028(2) 0.041(2) 0.001(2) 0.0132(18) -0.010(2) O5 0.0482(16) 0.0298(16) 0.0335(15) -0.0016(14) 0.0003(13) 0.0065(14) C4 0.0250(17) 0.033(2) 0.036(2) -0.0006(19) 0.0061(15) 0.0047(17) O4 0.0497(16) 0.045(2) 0.0456(17) 0.0056(16) -0.0204(14) -0.0005(15) O2 0.0323(13) 0.0434(18) 0.0324(14) 0.0153(14) 0.0059(11) 0.0017(13) C1 0.0283(17) 0.023(2) 0.0276(19) -0.0009(17) 0.0049(15) 0.0027(16) O3 0.0511(16) 0.0403(18) 0.0381(15) -0.0081(14) 0.0197(12) -0.0086(15) C13 0.089(3) 0.034(3) 0.053(3) -0.009(2) 0.030(2) -0.018(3) O1 0.0293(13) 0.0364(16) 0.0318(14) 0.0122(13) 0.0002(11) -0.0041(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 C12 C7 1.3900 . ? C12 N1 1.3900 . ? C12 C11 1.400(4) . ? C7 C6 1.3900 . ? C7 C8 1.429(5) . ? C6 C3 1.3900 . ? C6 H6 0.9300 . ? C3 C2 1.3900 . ? C3 C4 1.494(4) . ? C2 N1 1.3900 . ? C2 C1 1.486(4) . ? N1 Zn1 2.171(2) . ? Zn1 O1 2.000(3) 3_655 ? Zn1 O1 2.000(3) . ? Zn1 O3 2.101(3) 3_655 ? Zn1 O3 2.101(3) . ? Zn1 N1 2.171(2) 3_655 ? C8 C9 1.357(6) . ? C8 H8 0.9300 . ? C11 C10 1.359(6) . ? C11 H11 0.9300 . ? C10 C9 1.405(6) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? O5 C4 1.329(5) . ? O5 C5 1.426(6) . ? C4 O4 1.198(5) . ? O2 C1 1.225(4) . ? C1 O1 1.266(4) . ? O3 C13 1.399(6) . ? O3 H3 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C7 C12 N1 120.0 . . ? C7 C12 C11 120.1(2) . . ? N1 C12 C11 119.9(2) . . ? C12 C7 C6 120.0 . . ? C12 C7 C8 118.7(2) . . ? C6 C7 C8 121.1(2) . . ? C7 C6 C3 120.0 . . ? C7 C6 H6 120.0 . . ? C3 C6 H6 120.0 . . ? C2 C3 C6 120.0 . . ? C2 C3 C4 120.2(2) . . ? C6 C3 C4 119.6(2) . . ? C3 C2 N1 120.0 . . ? C3 C2 C1 123.56(19) . . ? N1 C2 C1 115.31(19) . . ? C2 N1 C12 120.0 . . ? C2 N1 Zn1 107.74(9) . . ? C12 N1 Zn1 132.25(9) . . ? O1 Zn1 O1 180.0(2) 3_655 . ? O1 Zn1 O3 88.26(13) 3_655 3_655 ? O1 Zn1 O3 91.74(13) . 3_655 ? O1 Zn1 O3 91.74(13) 3_655 . ? O1 Zn1 O3 88.26(13) . . ? O3 Zn1 O3 180.00(18) 3_655 . ? O1 Zn1 N1 99.69(9) 3_655 . ? O1 Zn1 N1 80.31(9) . . ? O3 Zn1 N1 91.72(10) 3_655 . ? O3 Zn1 N1 88.28(10) . . ? O1 Zn1 N1 80.31(16) 3_655 3_655 ? O1 Zn1 N1 99.69(16) . 3_655 ? O3 Zn1 N1 88.28(19) 3_655 3_655 ? O3 Zn1 N1 91.72(19) . 3_655 ? N1 Zn1 N1 180.0(2) . 3_655 ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C10 C9 121.8(4) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C8 C9 C10 119.1(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C4 O5 C5 115.5(3) . . ? O4 C4 O5 124.7(4) . . ? O4 C4 C3 124.1(4) . . ? O5 C4 C3 111.1(3) . . ? O2 C1 O1 126.3(4) . . ? O2 C1 C2 116.5(3) . . ? O1 C1 C2 117.2(3) . . ? C13 O3 Zn1 124.0(3) . . ? C13 O3 H3 118.0 . . ? Zn1 O3 H3 118.0 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 O1 Zn1 116.7(2) . . ? O5 C5 H5A 109.5 . . ? O5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 N1 C12 C7 C6 0.0 . . . . ? C11 C12 C7 C6 179.4(2) . . . . ? N1 C12 C7 C8 -175.8(2) . . . . ? C11 C12 C7 C8 3.6(3) . . . . ? C12 C7 C6 C3 0.0 . . . . ? C8 C7 C6 C3 175.7(3) . . . . ? C7 C6 C3 C2 0.0 . . . . ? C7 C6 C3 C4 174.4(2) . . . . ? C6 C3 C2 N1 0.0 . . . . ? C4 C3 C2 N1 -174.4(2) . . . . ? C6 C3 C2 C1 -167.2(2) . . . . ? C4 C3 C2 C1 18.4(3) . . . . ? C3 C2 N1 C12 0.0 . . . . ? C1 C2 N1 C12 168.3(2) . . . . ? C3 C2 N1 Zn1 178.99(11) . . . . ? C1 C2 N1 Zn1 -12.75(19) . . . . ? C7 C12 N1 C2 0.0 . . . . ? C11 C12 N1 C2 -179.4(2) . . . . ? C7 C12 N1 Zn1 -178.70(15) . . . . ? C11 C12 N1 Zn1 1.9(3) . . . . ? C2 N1 Zn1 O1 -176.00(10) . . . 3_655 ? C12 N1 Zn1 O1 2.82(15) . . . 3_655 ? C2 N1 Zn1 O1 4.00(10) . . . . ? C12 N1 Zn1 O1 -177.18(15) . . . . ? C2 N1 Zn1 O3 -87.47(12) . . . 3_655 ? C12 N1 Zn1 O3 91.35(15) . . . 3_655 ? C2 N1 Zn1 O3 92.53(12) . . . . ? C12 N1 Zn1 O3 -88.65(15) . . . . ? C2 N1 Zn1 N1 102(100) . . . 3_655 ? C12 N1 Zn1 N1 -79(100) . . . 3_655 ? C12 C7 C8 C9 -2.1(5) . . . . ? C6 C7 C8 C9 -177.9(3) . . . . ? C7 C12 C11 C10 -2.9(5) . . . . ? N1 C12 C11 C10 176.5(3) . . . . ? C12 C11 C10 C9 0.7(6) . . . . ? C7 C8 C9 C10 -0.1(6) . . . . ? C11 C10 C9 C8 0.8(7) . . . . ? C5 O5 C4 O4 14.2(6) . . . . ? C5 O5 C4 C3 -167.8(3) . . . . ? C2 C3 C4 O4 -127.7(3) . . . . ? C6 C3 C4 O4 57.9(4) . . . . ? C2 C3 C4 O5 54.3(4) . . . . ? C6 C3 C4 O5 -120.1(3) . . . . ? C3 C2 C1 O2 10.9(4) . . . . ? N1 C2 C1 O2 -156.9(3) . . . . ? C3 C2 C1 O1 -172.3(2) . . . . ? N1 C2 C1 O1 19.9(4) . . . . ? O1 Zn1 O3 C13 -40.9(3) 3_655 . . . ? O1 Zn1 O3 C13 139.1(3) . . . . ? O3 Zn1 O3 C13 -45(100) 3_655 . . . ? N1 Zn1 O3 C13 58.7(3) . . . . ? N1 Zn1 O3 C13 -121.3(4) 3_655 . . . ? O2 C1 O1 Zn1 160.4(3) . . . . ? C2 C1 O1 Zn1 -16.1(4) . . . . ? O1 Zn1 O1 C1 0(100) 3_655 . . . ? O3 Zn1 O1 C1 98.2(3) 3_655 . . . ? O3 Zn1 O1 C1 -81.8(3) . . . . ? N1 Zn1 O1 C1 6.8(3) . . . . ? N1 Zn1 O1 C1 -173.2(3) 3_655 . . . ? 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 H3 O2 0.93 1.98 2.710(4) 134.4 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.108 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.180 ################ END ################# data_849598(5) _database_code_depnum_ccdc_archive 'CCDC 849600' #TrackingRef '- eight cif files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 N2 O4 Zn' _chemical_formula_sum 'C20 H12 N2 O4 Zn' _chemical_formula_weight 409.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.004(9) _cell_length_b 8.040(3) _cell_length_c 15.251(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.337(4) _cell_angle_gamma 90.00 _cell_volume 3240.3(18) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 459 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 18.55 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.680 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.547 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6891 _exptl_absorpt_correction_T_max 0.8361 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8016 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.1104 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.19 _reflns_number_total 2921 _reflns_number_gt 1652 _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^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2921 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1131 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.12649(2) 0.62177(8) 0.43298(5) 0.0337(2) Uani 1 1 d . . . O1 O 0.10341(16) -0.0261(5) 0.3711(3) 0.0537(13) Uani 1 1 d . . . O2 O 0.16418(15) -0.1769(5) 0.4801(3) 0.0447(12) Uani 1 1 d . . . O3 O 0.14469(16) 0.4092(6) 0.7787(3) 0.0528(13) Uani 1 1 d . . . O4 O 0.07932(15) 0.4724(5) 0.8103(3) 0.0440(11) Uani 1 1 d . . . N1 N 0.17259(16) 0.4139(5) 0.4941(3) 0.0302(12) Uani 1 1 d . . . N2 N 0.08072(16) 0.6242(6) 0.5097(3) 0.0308(11) Uani 1 1 d . . . C1 C 0.1519(2) 0.2692(7) 0.4558(4) 0.0306(14) Uani 1 1 d . . . H1 H 0.1215 0.2721 0.4012 0.037 Uiso 1 1 calc R . . C2 C 0.1721(2) 0.1134(7) 0.4911(4) 0.0301(14) Uani 1 1 d . . . C3 C 0.1434(2) -0.0406(8) 0.4416(4) 0.0333(15) Uani 1 1 d . . . C4 C 0.2163(2) 0.1114(7) 0.5701(4) 0.0344(14) Uani 1 1 d . . . H4 H 0.2307 0.0093 0.5956 0.041 Uiso 1 1 calc R . . C5 C 0.2416(2) 0.2575(8) 0.6152(4) 0.0364(15) Uani 1 1 d . . . C6 C 0.2875(2) 0.2585(8) 0.6963(4) 0.0462(18) Uani 1 1 d . . . H6 H 0.3027 0.1587 0.7243 0.055 Uiso 1 1 calc R . . C7 C 0.3101(2) 0.4057(9) 0.7344(5) 0.0529(19) Uani 1 1 d . . . H7 H 0.3404 0.4057 0.7890 0.064 Uiso 1 1 calc R . . C8 C 0.2885(2) 0.5556(9) 0.6930(4) 0.0500(18) Uani 1 1 d . . . H8 H 0.3049 0.6551 0.7186 0.060 Uiso 1 1 calc R . . C9 C 0.2433(2) 0.5575(8) 0.6149(4) 0.0429(17) Uani 1 1 d . . . H9 H 0.2287 0.6587 0.5882 0.051 Uiso 1 1 calc R . . C10 C 0.2183(2) 0.4096(7) 0.5743(4) 0.0325(15) Uani 1 1 d . . . C11 C 0.1000(2) 0.5562(7) 0.5965(4) 0.0359(15) Uani 1 1 d . . . H11 H 0.1312 0.5033 0.6161 0.043 Uiso 1 1 calc R . . C12 C 0.0768(2) 0.5582(7) 0.6605(4) 0.0351(15) Uani 1 1 d . . . C13 C 0.1029(3) 0.4702(7) 0.7552(4) 0.0386(16) Uani 1 1 d . . . C14 C 0.0323(2) 0.6394(7) 0.6333(4) 0.0357(15) Uani 1 1 d . . . H14 H 0.0163 0.6435 0.6750 0.043 Uiso 1 1 calc R . . C15 C 0.0096(2) 0.7182(7) 0.5429(4) 0.0339(14) Uani 1 1 d . . . C16 C -0.0366(2) 0.8042(8) 0.5111(5) 0.0446(17) Uani 1 1 d . . . H16 H -0.0533 0.8145 0.5514 0.053 Uiso 1 1 calc R . . C17 C -0.0569(2) 0.8727(8) 0.4213(5) 0.0481(17) Uani 1 1 d . . . H17 H -0.0872 0.9311 0.4011 0.058 Uiso 1 1 calc R . . C18 C -0.0327(2) 0.8560(8) 0.3596(4) 0.0443(17) Uani 1 1 d . . . H18 H -0.0475 0.9000 0.2977 0.053 Uiso 1 1 calc R . . C19 C 0.0121(2) 0.7762(7) 0.3894(4) 0.0372(15) Uani 1 1 d . . . H19 H 0.0281 0.7681 0.3478 0.045 Uiso 1 1 calc R . . C20 C 0.0350(2) 0.7056(7) 0.4804(4) 0.0316(14) 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 Zn1 0.0429(4) 0.0248(4) 0.0320(4) -0.0018(3) 0.0142(3) -0.0013(4) O1 0.048(3) 0.043(3) 0.051(3) -0.008(2) 0.002(2) -0.007(2) O2 0.056(3) 0.019(2) 0.052(3) -0.0008(19) 0.015(2) -0.004(2) O3 0.052(3) 0.053(3) 0.046(3) 0.012(2) 0.012(2) 0.017(3) O4 0.050(3) 0.048(3) 0.030(3) 0.006(2) 0.013(2) -0.008(2) N1 0.035(3) 0.027(3) 0.028(3) -0.006(2) 0.011(2) -0.002(2) N2 0.036(3) 0.032(3) 0.020(3) -0.001(2) 0.007(2) -0.002(3) C1 0.033(3) 0.027(4) 0.035(4) -0.004(3) 0.016(3) -0.006(3) C2 0.031(3) 0.021(3) 0.037(4) -0.001(3) 0.013(3) 0.002(3) C3 0.036(4) 0.023(3) 0.045(4) -0.006(3) 0.021(3) -0.004(3) C4 0.042(4) 0.024(3) 0.038(4) 0.000(3) 0.018(3) -0.001(3) C5 0.039(4) 0.035(4) 0.032(4) 0.002(3) 0.010(3) -0.003(3) C6 0.044(4) 0.041(4) 0.047(4) 0.003(3) 0.011(4) 0.008(3) C7 0.052(4) 0.050(5) 0.044(4) -0.006(4) 0.007(4) -0.011(4) C8 0.053(4) 0.046(5) 0.043(5) -0.016(3) 0.012(4) -0.021(4) C9 0.054(4) 0.030(4) 0.044(4) 0.000(3) 0.020(4) -0.002(3) C10 0.031(3) 0.036(4) 0.034(4) 0.002(3) 0.017(3) -0.004(3) C11 0.036(4) 0.028(3) 0.037(4) -0.004(3) 0.008(3) -0.002(3) C12 0.045(4) 0.029(4) 0.032(4) -0.001(3) 0.016(3) -0.004(3) C13 0.057(5) 0.026(4) 0.031(4) -0.003(3) 0.015(4) -0.011(3) C14 0.047(4) 0.036(4) 0.029(4) -0.003(3) 0.020(3) -0.006(3) C15 0.040(4) 0.030(4) 0.031(4) -0.007(3) 0.014(3) -0.006(3) C16 0.043(4) 0.044(4) 0.053(5) -0.003(3) 0.026(4) 0.002(3) C17 0.038(4) 0.046(4) 0.051(4) 0.008(4) 0.009(4) 0.011(3) C18 0.043(4) 0.046(4) 0.033(4) -0.002(3) 0.005(3) 0.001(4) C19 0.042(4) 0.033(4) 0.031(4) 0.002(3) 0.010(3) 0.006(3) C20 0.038(4) 0.021(3) 0.032(4) -0.005(3) 0.011(3) -0.002(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 O2 1.920(4) 1_565 ? Zn1 O4 1.958(4) 6_565 ? Zn1 N2 2.101(4) . ? Zn1 N1 2.103(4) . ? O1 C3 1.220(6) . ? O2 C3 1.271(7) . ? O2 Zn1 1.920(4) 1_545 ? O3 C13 1.216(7) . ? O4 C13 1.285(7) . ? O4 Zn1 1.958(4) 6_566 ? N1 C1 1.329(6) . ? N1 C10 1.385(6) . ? N2 C11 1.324(6) . ? N2 C20 1.379(7) . ? C1 C2 1.394(7) . ? C1 H1 0.9300 . ? C2 C4 1.350(7) . ? C2 C3 1.509(7) . ? C4 C5 1.405(7) . ? C4 H4 0.9300 . ? C5 C6 1.395(7) . ? C5 C10 1.412(8) . ? C6 C7 1.361(8) . ? C6 H6 0.9300 . ? C7 C8 1.384(8) . ? C7 H7 0.9300 . ? C8 C9 1.361(7) . ? C8 H8 0.9300 . ? C9 C10 1.397(8) . ? C9 H9 0.9300 . ? C11 C12 1.396(8) . ? C11 H11 0.9300 . ? C12 C14 1.349(7) . ? C12 C13 1.503(8) . ? C14 C15 1.410(7) . ? C14 H14 0.9300 . ? C15 C16 1.404(8) . ? C15 C20 1.427(8) . ? C16 C17 1.365(8) . ? C16 H16 0.9300 . ? C17 C18 1.393(8) . ? C17 H17 0.9300 . ? C18 C19 1.349(7) . ? C18 H18 0.9300 . ? C19 C20 1.390(7) . ? C19 H19 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 O4 138.55(18) 1_565 6_565 ? O2 Zn1 N2 100.16(17) 1_565 . ? O4 Zn1 N2 100.54(17) 6_565 . ? O2 Zn1 N1 110.13(17) 1_565 . ? O4 Zn1 N1 100.53(17) 6_565 . ? N2 Zn1 N1 101.11(18) . . ? C3 O2 Zn1 117.8(4) . 1_545 ? C13 O4 Zn1 105.6(4) . 6_566 ? C1 N1 C10 117.4(5) . . ? C1 N1 Zn1 114.3(4) . . ? C10 N1 Zn1 127.9(4) . . ? C11 N2 C20 118.3(5) . . ? C11 N2 Zn1 116.7(4) . . ? C20 N2 Zn1 124.7(4) . . ? N1 C1 C2 125.1(5) . . ? N1 C1 H1 117.4 . . ? C2 C1 H1 117.4 . . ? C4 C2 C1 116.7(5) . . ? C4 C2 C3 124.2(5) . . ? C1 C2 C3 119.1(5) . . ? O1 C3 O2 125.9(6) . . ? O1 C3 C2 119.4(6) . . ? O2 C3 C2 114.7(5) . . ? C2 C4 C5 122.6(6) . . ? C2 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C6 C5 C4 123.6(6) . . ? C6 C5 C10 119.7(6) . . ? C4 C5 C10 116.7(5) . . ? C7 C6 C5 119.9(6) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 121.0(6) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 120.0(6) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.0(6) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? N1 C10 C9 120.2(5) . . ? N1 C10 C5 121.5(5) . . ? C9 C10 C5 118.3(6) . . ? N2 C11 C12 124.5(6) . . ? N2 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C14 C12 C11 117.8(6) . . ? C14 C12 C13 124.3(6) . . ? C11 C12 C13 117.9(6) . . ? O3 C13 O4 123.2(6) . . ? O3 C13 C12 121.4(6) . . ? O4 C13 C12 115.4(6) . . ? C12 C14 C15 121.3(5) . . ? C12 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 123.6(6) . . ? C16 C15 C20 119.1(6) . . ? C14 C15 C20 117.3(6) . . ? C17 C16 C15 120.0(6) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.7(6) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 120.1(6) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 121.8(6) . . ? C18 C19 H19 119.1 . . ? C20 C19 H19 119.1 . . ? N2 C20 C19 121.1(6) . . ? N2 C20 C15 120.6(5) . . ? C19 C20 C15 118.2(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Zn1 N1 C1 -171.2(4) 1_565 . . . ? O4 Zn1 N1 C1 -19.5(4) 6_565 . . . ? N2 Zn1 N1 C1 83.5(4) . . . . ? O2 Zn1 N1 C10 16.4(5) 1_565 . . . ? O4 Zn1 N1 C10 168.1(4) 6_565 . . . ? N2 Zn1 N1 C10 -88.8(4) . . . . ? O2 Zn1 N2 C11 -87.0(4) 1_565 . . . ? O4 Zn1 N2 C11 129.1(4) 6_565 . . . ? N1 Zn1 N2 C11 26.0(4) . . . . ? O2 Zn1 N2 C20 86.0(4) 1_565 . . . ? O4 Zn1 N2 C20 -57.8(5) 6_565 . . . ? N1 Zn1 N2 C20 -160.9(4) . . . . ? C10 N1 C1 C2 1.2(8) . . . . ? Zn1 N1 C1 C2 -172.0(4) . . . . ? N1 C1 C2 C4 -0.3(8) . . . . ? N1 C1 C2 C3 178.1(5) . . . . ? Zn1 O2 C3 O1 -7.2(8) 1_545 . . . ? Zn1 O2 C3 C2 172.0(3) 1_545 . . . ? C4 C2 C3 O1 179.2(5) . . . . ? C1 C2 C3 O1 0.8(8) . . . . ? C4 C2 C3 O2 -0.1(8) . . . . ? C1 C2 C3 O2 -178.4(5) . . . . ? C1 C2 C4 C5 -0.5(8) . . . . ? C3 C2 C4 C5 -178.9(5) . . . . ? C2 C4 C5 C6 -179.3(6) . . . . ? C2 C4 C5 C10 0.4(9) . . . . ? C4 C5 C6 C7 178.5(6) . . . . ? C10 C5 C6 C7 -1.2(9) . . . . ? C5 C6 C7 C8 -1.0(10) . . . . ? C6 C7 C8 C9 2.1(10) . . . . ? C7 C8 C9 C10 -1.0(10) . . . . ? C1 N1 C10 C9 176.7(5) . . . . ? Zn1 N1 C10 C9 -11.2(7) . . . . ? C1 N1 C10 C5 -1.3(8) . . . . ? Zn1 N1 C10 C5 170.9(4) . . . . ? C8 C9 C10 N1 -179.2(5) . . . . ? C8 C9 C10 C5 -1.2(9) . . . . ? C6 C5 C10 N1 -179.7(5) . . . . ? C4 C5 C10 N1 0.5(8) . . . . ? C6 C5 C10 C9 2.3(8) . . . . ? C4 C5 C10 C9 -177.5(5) . . . . ? C20 N2 C11 C12 1.2(8) . . . . ? Zn1 N2 C11 C12 174.7(4) . . . . ? N2 C11 C12 C14 -2.1(9) . . . . ? N2 C11 C12 C13 178.0(5) . . . . ? Zn1 O4 C13 O3 4.4(7) 6_566 . . . ? Zn1 O4 C13 C12 -172.1(4) 6_566 . . . ? C14 C12 C13 O3 -174.7(6) . . . . ? C11 C12 C13 O3 5.2(9) . . . . ? C14 C12 C13 O4 1.8(9) . . . . ? C11 C12 C13 O4 -178.3(5) . . . . ? C11 C12 C14 C15 0.7(9) . . . . ? C13 C12 C14 C15 -179.4(5) . . . . ? C12 C14 C15 C16 180.0(6) . . . . ? C12 C14 C15 C20 1.3(9) . . . . ? C14 C15 C16 C17 -177.9(6) . . . . ? C20 C15 C16 C17 0.8(9) . . . . ? C15 C16 C17 C18 1.1(10) . . . . ? C16 C17 C18 C19 -2.2(10) . . . . ? C17 C18 C19 C20 1.3(9) . . . . ? C11 N2 C20 C19 -178.4(5) . . . . ? Zn1 N2 C20 C19 8.6(7) . . . . ? C11 N2 C20 C15 1.0(8) . . . . ? Zn1 N2 C20 C15 -172.0(4) . . . . ? C18 C19 C20 N2 179.9(5) . . . . ? C18 C19 C20 C15 0.5(9) . . . . ? C16 C15 C20 N2 179.1(5) . . . . ? C14 C15 C20 N2 -2.2(8) . . . . ? C16 C15 C20 C19 -1.5(8) . . . . ? C14 C15 C20 C19 177.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.630 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.102