data_compound_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H8 Co F4 N2 O3' _chemical_formula_weight 423.18 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' 'F' 'F' 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M Pmna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x+1/2, y, -z+1/2' 'x, -y, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x-1/2, -y, z-1/2' '-x, y, z' _cell_length_a 26.271(4) _cell_length_b 8.9909(12) _cell_length_c 6.4018(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1512.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description purple _exptl_crystal_colour block _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 1.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.741 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10070 _diffrn_reflns_av_R_equivalents 0.2195 _diffrn_reflns_av_sigmaI/netI 0.1338 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 24.71 _reflns_number_total 1318 _reflns_number_gt 699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0508P)^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 1318 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _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 0.28523(4) 0.0000 0.0000 0.0230(4) Uani 1 2 d S . . C1 C 0.2500 0.2583(8) 0.2500 0.0187(19) Uani 1 2 d S . . C2 C 0.2500 0.4269(9) 0.2500 0.0235(19) Uani 1 2 d S . . C3 C 0.20599(18) 0.5084(6) 0.2437(8) 0.0214(12) Uani 1 1 d . . . C4 C 0.2059(2) 0.6628(6) 0.2395(9) 0.0232(14) Uani 1 1 d . . . C5 C 0.2500 0.7440(8) 0.2500 0.0209(19) Uani 1 2 d S . . C6 C 0.3913(2) 0.0719(8) 0.1428(11) 0.0424(19) Uani 1 1 d . . . H6 H 0.3735 0.1233 0.2456 0.08(3) Uiso 1 1 calc R . . C7 C 0.4439(2) 0.0750(8) 0.1481(12) 0.048(2) Uani 1 1 d . . . H7 H 0.4606 0.1280 0.2521 0.036(17) Uiso 1 1 calc R . . C8 C 0.4713(3) 0.0000 0.0000 0.0292(19) Uani 1 2 d S . . C9 C 0.4583(3) 0.6798(10) 0.3666(14) 0.071(3) Uani 1 1 d . . . H9 H 0.4275 0.7094 0.4252 0.12(4) Uiso 1 1 calc R . . C10 C 0.4565(3) 0.5925(9) 0.1886(13) 0.066(2) Uani 1 1 d . . . H10 H 0.4251 0.5648 0.1334 0.07(3) Uiso 1 1 calc R . . C11 C 0.5000 0.5470(10) 0.0941(15) 0.037(2) Uani 1 2 d S . . N1 N 0.3650(2) 0.0000 0.0000 0.0243(15) Uani 1 2 d S . . N2 N 0.5000 0.7235(10) 0.4580(13) 0.056(3) Uani 1 2 d S . . O1 O 0.28692(14) 0.1958(4) 0.1638(6) 0.0290(10) Uani 1 1 d . . . O2 O 0.2500 0.8949(6) 0.2500 0.0314(15) Uani 1 2 d S . . F1 F 0.15987(11) 0.4412(3) 0.2340(6) 0.0396(10) Uani 1 1 d . . . F2 F 0.16077(11) 0.7346(3) 0.2272(6) 0.0419(11) 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 0.0237(6) 0.0150(6) 0.0304(6) 0.0013(6) 0.000 0.000 C1 0.022(5) 0.011(4) 0.023(5) 0.000 0.002(4) 0.000 C2 0.038(5) 0.017(4) 0.016(4) 0.000 -0.004(4) 0.000 C3 0.022(3) 0.018(3) 0.024(3) 0.001(3) 0.003(2) -0.004(3) C4 0.023(3) 0.021(3) 0.026(3) -0.001(3) 0.005(3) 0.009(3) C5 0.041(5) 0.005(4) 0.017(5) 0.000 -0.006(4) 0.000 C6 0.023(4) 0.061(5) 0.043(4) -0.030(4) 0.001(3) 0.002(3) C7 0.030(4) 0.060(5) 0.055(5) -0.029(4) -0.007(4) -0.001(4) C8 0.013(4) 0.029(4) 0.046(5) 0.006(5) 0.000 0.000 C9 0.042(5) 0.097(7) 0.076(6) -0.038(6) 0.009(5) -0.007(5) C10 0.033(5) 0.097(7) 0.067(6) -0.033(5) -0.004(4) -0.005(5) C11 0.026(5) 0.043(6) 0.041(5) 0.002(4) 0.000 0.000 N1 0.017(3) 0.025(3) 0.030(4) -0.003(4) 0.000 0.000 N2 0.035(5) 0.066(6) 0.068(7) -0.026(5) 0.000 0.000 O1 0.029(2) 0.0139(19) 0.045(3) -0.0010(18) 0.008(2) -0.003(2) O2 0.041(4) 0.015(3) 0.037(4) 0.000 -0.003(3) 0.000 F1 0.0252(19) 0.0228(19) 0.071(3) -0.0032(18) 0.0010(19) -0.0036(16) F2 0.031(2) 0.0201(19) 0.074(3) 0.0016(18) -0.0027(19) 0.0055(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.050(4) . ? Co1 O1 2.050(4) 4 ? Co1 O2 2.076(2) 2_564 ? Co1 O2 2.076(2) 1_545 ? Co1 N1 2.096(6) . ? C1 O1 1.249(5) . ? C1 O1 1.249(5) 3 ? C1 C2 1.516(10) . ? C2 C3 1.370(6) 3 ? C2 C3 1.370(6) . ? C3 F1 1.355(5) . ? C3 C4 1.389(8) . ? C4 F2 1.351(5) . ? C4 C5 1.372(6) . ? C5 O2 1.356(9) . ? C5 C4 1.372(6) 3 ? C6 N1 1.315(7) . ? C6 C7 1.383(8) . ? C7 C8 1.368(7) . ? C8 C7 1.368(7) 4 ? C8 C8 1.510(14) 5_655 ? C9 N2 1.303(8) . ? C9 C10 1.384(11) . ? C10 C11 1.357(8) . ? C11 C10 1.357(8) 8_655 ? C11 C11 1.471(18) 5_665 ? N1 C6 1.315(7) 4 ? N2 C9 1.303(8) 8_655 ? O2 Co1 2.076(2) 1_565 ? O2 Co1 2.076(2) 2_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 177.5(2) . 4 ? O1 Co1 O2 90.75(16) . 2_564 ? O1 Co1 O2 90.36(16) 4 2_564 ? O1 Co1 O2 90.36(16) . 1_545 ? O1 Co1 O2 90.75(16) 4 1_545 ? O2 Co1 O2 127.06(8) 2_564 1_545 ? O1 Co1 N1 88.75(11) . . ? O1 Co1 N1 88.75(11) 4 . ? O2 Co1 N1 116.47(4) 2_564 . ? O2 Co1 N1 116.47(4) 1_545 . ? O1 C1 O1 126.6(7) . 3 ? O1 C1 C2 116.7(3) . . ? O1 C1 C2 116.7(3) 3 . ? C3 C2 C3 115.3(7) 3 . ? C3 C2 C1 122.4(3) 3 . ? C3 C2 C1 122.4(3) . . ? F1 C3 C2 121.1(5) . . ? F1 C3 C4 116.3(4) . . ? C2 C3 C4 122.5(5) . . ? F2 C4 C5 119.3(5) . . ? F2 C4 C3 118.7(5) . . ? C5 C4 C3 121.9(5) . . ? O2 C5 C4 122.1(3) . 3 ? O2 C5 C4 122.1(3) . . ? C4 C5 C4 115.7(7) 3 . ? N1 C6 C7 123.4(6) . . ? C8 C7 C6 119.9(6) . . ? C7 C8 C7 116.5(8) . 4 ? C7 C8 C8 121.7(4) . 5_655 ? C7 C8 C8 121.7(4) 4 5_655 ? N2 C9 C10 124.8(8) . . ? C11 C10 C9 120.6(8) . . ? C10 C11 C10 114.9(9) 8_655 . ? C10 C11 C11 122.6(5) 8_655 5_665 ? C10 C11 C11 122.6(5) . 5_665 ? C6 N1 C6 116.7(7) 4 . ? C6 N1 Co1 121.6(3) 4 . ? C6 N1 Co1 121.6(3) . . ? C9 N2 C9 114.5(10) 8_655 . ? C1 O1 Co1 126.5(4) . . ? C5 O2 Co1 117.07(12) . 1_565 ? C5 O2 Co1 117.07(12) . 2_565 ? Co1 O2 Co1 125.9(2) 1_565 2_565 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.057 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.128 #===END data_compound_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H8 F4 N2 O3 Zn' _chemical_formula_weight 429.62 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x+1/2, y, -z+1/2' 'x, -y, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x-1/2, -y, z-1/2' '-x, y, z' _cell_length_a 26.376(3) _cell_length_b 8.9842(10) _cell_length_c 6.3964(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1515.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colorless _exptl_crystal_colour plate _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.655 _exptl_absorpt_correction_T_max 0.919 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10734 _diffrn_reflns_av_R_equivalents 0.1175 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1430 _reflns_number_gt 885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0603P)^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 1430 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.28656(2) 0.0000 0.0000 0.0203(2) Uani 1 2 d S . . C1 C 0.2500 0.2567(6) 0.2500 0.0206(14) Uani 1 2 d S . . C2 C 0.2500 0.4246(7) 0.2500 0.0198(14) Uani 1 2 d S . . C3 C 0.20573(14) 0.5077(5) 0.2454(6) 0.0223(10) Uani 1 1 d . . . C4 C 0.20565(16) 0.6615(5) 0.2416(7) 0.0251(11) Uani 1 1 d . . . C5 C 0.2500 0.7446(6) 0.2500 0.0207(14) Uani 1 2 d S . . C6 C 0.39191(19) 0.0711(6) 0.1455(9) 0.0431(14) Uani 1 1 d . . . H6 H 0.3744 0.1216 0.2499 0.10(2) Uiso 1 1 calc R . . C7 C 0.44389(18) 0.0739(6) 0.1499(9) 0.0475(15) Uani 1 1 d . . . H7 H 0.4606 0.1261 0.2548 0.056(17) Uiso 1 1 calc R . . C8 C 0.4714(2) 0.0000 0.0000 0.0260(14) Uani 1 2 d S . . C9 C 0.4581(2) 0.6806(8) 0.3669(11) 0.070(2) Uani 1 1 d . . . H9 H 0.4275 0.7099 0.4262 0.09(2) Uiso 1 1 calc R . . C10 C 0.4561(2) 0.5941(8) 0.1884(10) 0.0628(19) Uani 1 1 d . . . H10 H 0.4249 0.5689 0.1307 0.063(19) Uiso 1 1 calc R . . C11 C 0.5000 0.5453(8) 0.0961(12) 0.0365(18) Uani 1 2 d S . . N1 N 0.36525(18) 0.0000 0.0000 0.0237(11) Uani 1 2 d S . . N2 N 0.5000 0.7245(8) 0.4590(11) 0.057(2) Uani 1 2 d S . . O1 O 0.28689(11) 0.1939(3) 0.1638(5) 0.0254(7) Uani 1 1 d . . . O2 O 0.2500 0.8939(4) 0.2500 0.0264(11) Uani 1 2 d S . . F1 F 0.16001(9) 0.4395(3) 0.2362(5) 0.0385(7) Uani 1 1 d . . . F2 F 0.16083(9) 0.7337(3) 0.2294(5) 0.0381(8) 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 0.0203(4) 0.0149(4) 0.0258(4) -0.0010(4) 0.000 0.000 C1 0.024(3) 0.016(3) 0.022(4) 0.000 -0.009(3) 0.000 C2 0.031(4) 0.020(3) 0.009(3) 0.000 -0.005(3) 0.000 C3 0.024(2) 0.021(2) 0.022(2) 0.001(2) 0.0018(17) -0.006(2) C4 0.028(3) 0.020(2) 0.027(3) -0.001(2) 0.001(2) 0.007(2) C5 0.032(4) 0.012(3) 0.018(4) 0.000 0.003(3) 0.000 C6 0.031(3) 0.056(4) 0.042(3) -0.025(3) 0.003(3) 0.007(3) C7 0.025(3) 0.063(4) 0.055(4) -0.034(3) -0.006(3) 0.001(3) C8 0.012(3) 0.028(3) 0.039(4) 0.004(4) 0.000 0.000 C9 0.046(4) 0.092(5) 0.072(5) -0.042(4) 0.004(4) 0.006(4) C10 0.036(4) 0.087(5) 0.066(4) -0.031(4) -0.001(3) 0.000(3) C11 0.026(4) 0.041(5) 0.042(4) 0.000(3) 0.000 0.000 N1 0.021(3) 0.019(2) 0.031(3) -0.005(3) 0.000 0.000 N2 0.043(4) 0.067(5) 0.062(6) -0.015(4) 0.000 0.000 O1 0.0254(16) 0.0179(16) 0.0330(19) -0.0021(14) 0.0050(15) -0.0007(15) O2 0.035(3) 0.013(2) 0.031(3) 0.000 0.002(2) 0.000 F1 0.0223(14) 0.0238(14) 0.069(2) -0.0008(15) 0.0002(14) -0.0038(12) F2 0.0284(15) 0.0235(15) 0.062(2) 0.0005(14) 0.0004(14) 0.0071(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.033(3) 4 ? Zn1 O1 2.033(3) . ? Zn1 N1 2.075(5) . ? Zn1 O2 2.0967(18) 2_564 ? Zn1 O2 2.0967(18) 1_545 ? C1 O1 1.253(4) . ? C1 O1 1.253(4) 3 ? C1 C2 1.508(8) . ? C2 C3 1.386(5) 3 ? C2 C3 1.386(5) . ? C3 F1 1.354(4) . ? C3 C4 1.383(6) . ? C4 F2 1.351(4) . ? C4 C5 1.388(5) . ? C5 O2 1.342(7) . ? C5 C4 1.388(5) 3 ? C6 N1 1.330(6) . ? C6 C7 1.371(7) . ? C7 C8 1.374(6) . ? C8 C7 1.374(6) 4 ? C8 C8 1.508(11) 5_655 ? C9 N2 1.313(7) . ? C9 C10 1.383(8) . ? C10 C11 1.371(7) . ? C11 C10 1.371(7) 8_655 ? C11 C11 1.474(15) 5_665 ? N1 C6 1.330(6) 4 ? N2 C9 1.313(7) 8_655 ? O2 Zn1 2.0967(18) 1_565 ? O2 Zn1 2.0967(18) 2_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 179.52(16) 4 . ? O1 Zn1 N1 89.76(8) 4 . ? O1 Zn1 N1 89.76(8) . . ? O1 Zn1 O2 89.92(12) 4 2_564 ? O1 Zn1 O2 90.30(12) . 2_564 ? N1 Zn1 O2 117.38(3) . 2_564 ? O1 Zn1 O2 90.30(12) 4 1_545 ? O1 Zn1 O2 89.92(12) . 1_545 ? N1 Zn1 O2 117.38(3) . 1_545 ? O2 Zn1 O2 125.23(6) 2_564 1_545 ? O1 C1 O1 126.5(5) . 3 ? O1 C1 C2 116.8(3) . . ? O1 C1 C2 116.8(3) 3 . ? C3 C2 C3 114.8(5) 3 . ? C3 C2 C1 122.6(3) 3 . ? C3 C2 C1 122.6(3) . . ? F1 C3 C4 116.8(4) . . ? F1 C3 C2 120.5(4) . . ? C4 C3 C2 122.7(4) . . ? F2 C4 C3 118.8(4) . . ? F2 C4 C5 118.8(4) . . ? C3 C4 C5 122.3(4) . . ? O2 C5 C4 122.5(3) . 3 ? O2 C5 C4 122.5(3) . . ? C4 C5 C4 115.0(5) 3 . ? N1 C6 C7 123.5(5) . . ? C6 C7 C8 120.4(5) . . ? C7 C8 C7 116.2(6) . 4 ? C7 C8 C8 121.9(3) . 5_655 ? C7 C8 C8 121.9(3) 4 5_655 ? N2 C9 C10 124.8(6) . . ? C11 C10 C9 120.2(6) . . ? C10 C11 C10 115.1(8) 8_655 . ? C10 C11 C11 122.4(4) 8_655 5_665 ? C10 C11 C11 122.4(4) . 5_665 ? C6 N1 C6 116.2(6) . 4 ? C6 N1 Zn1 121.9(3) . . ? C6 N1 Zn1 121.9(3) 4 . ? C9 N2 C9 114.7(8) 8_655 . ? C1 O1 Zn1 127.6(3) . . ? C5 O2 Zn1 117.05(9) . 1_565 ? C5 O2 Zn1 117.05(9) . 2_565 ? Zn1 O2 Zn1 125.91(19) 1_565 2_565 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.111 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.120