# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Huabin Zhang' _publ_contact_author_email swdu@fjirsm.ac.cn loop_ _publ_author_name 'Huabin Zhang' 'Shaowu Du' data_1P-1 _database_code_depnum_ccdc_archive 'CCDC 862098' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' 'y, x, -z' _cell_length_a 11.9088(4) _cell_length_b 11.9088(4) _cell_length_c 8.3166(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1021.44(9) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3039 _cell_measurement_theta_min 2.4489 _cell_measurement_theta_max 27.4797 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.832 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6094 _exptl_absorpt_correction_T_max 0.7108 _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 ; Mercury2 (1x1 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8077 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.43 _reflns_number_total 1565 _reflns_number_gt 1528 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.4694P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.020(18) _refine_ls_number_reflns 1565 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn -0.71214(3) 0.28786(3) -0.5000 0.02558(14) Uani 1 2 d S . . O3 O -0.7863(2) 0.12874(17) -0.3452(2) 0.0320(4) Uani 1 1 d . . . O1 O -0.1734(2) 0.6229(3) 0.0296(2) 0.0354(5) Uani 1 1 d . . . O2 O -0.1260(2) 0.7705(2) -0.1637(3) 0.0405(6) Uani 1 1 d . . . C2 C -0.4053(3) 0.4459(3) -0.1260(3) 0.0385(7) Uani 1 1 d . . . H2 H -0.3908 0.4203 -0.0261 0.046 Uiso 1 1 calc R . . C3 C -0.3168(3) 0.5666(3) -0.1888(3) 0.0273(5) Uani 1 1 d . . . C6 C -0.1950(3) 0.6617(3) -0.1005(3) 0.0283(6) Uani 1 1 d . . . C4 C -0.3432(3) 0.5993(3) -0.3385(3) 0.0279(6) Uani 1 1 d . . . H4 H -0.2861 0.6792 -0.3842 0.034 Uiso 1 1 calc R . . C5 C -0.4549(3) 0.5126(2) -0.4201(3) 0.0247(5) Uani 1 1 d . . . C1 C -0.5156(3) 0.3639(3) -0.2139(3) 0.0398(8) Uani 1 1 d . . . H1 H -0.5749 0.2837 -0.1707 0.048 Uiso 1 1 calc R . . N1 N -0.5392(2) 0.3967(2) -0.3596(3) 0.0282(5) Uani 1 1 d . . . H3B H -0.8288 0.0481 -0.3747 0.034 Uiso 1 1 d R . . H3A H -0.8444 0.1366 -0.2877 0.034 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02612(18) 0.02612(18) 0.01970(19) -0.00222(8) 0.00222(8) 0.00947(19) O3 0.0376(12) 0.0256(9) 0.0323(9) -0.0009(7) 0.0067(10) 0.0153(10) O1 0.0367(11) 0.0325(12) 0.0287(9) 0.0038(10) -0.0135(9) 0.0112(10) O2 0.0371(12) 0.0322(11) 0.0406(12) 0.0080(9) -0.0133(9) 0.0087(9) C2 0.0415(15) 0.0327(16) 0.0267(12) 0.0072(12) -0.0096(11) 0.0077(15) C3 0.0297(13) 0.0276(15) 0.0214(11) -0.0009(10) -0.0040(10) 0.0119(12) C6 0.0294(13) 0.0271(14) 0.0261(12) -0.0019(11) -0.0070(10) 0.0124(11) C4 0.0268(13) 0.0252(13) 0.0249(12) 0.0031(10) -0.0032(10) 0.0078(11) C5 0.0280(13) 0.0253(13) 0.0178(11) 0.0004(9) -0.0020(10) 0.0111(11) C1 0.0440(17) 0.0305(16) 0.0270(13) 0.0091(12) -0.0058(12) 0.0053(13) N1 0.0304(11) 0.0248(13) 0.0207(9) -0.0010(9) -0.0047(9) 0.0071(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.0870(18) 6_464 ? Zn1 O3 2.0870(18) . ? Zn1 O1 2.1208(19) 2_564 ? Zn1 O1 2.1208(19) 4_564 ? Zn1 N1 2.148(2) . ? Zn1 N1 2.148(2) 6_464 ? O1 C6 1.253(3) . ? O1 Zn1 2.1208(19) 3_455 ? O2 C6 1.252(4) . ? C2 C1 1.389(4) . ? C2 C3 1.392(4) . ? C3 C4 1.387(4) . ? C3 C6 1.510(4) . ? C4 C5 1.387(4) . ? C5 N1 1.334(3) . ? C5 C5 1.489(5) 6_464 ? C1 N1 1.345(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 96.54(13) 6_464 . ? O3 Zn1 O1 91.83(7) 6_464 2_564 ? O3 Zn1 O1 89.29(11) . 2_564 ? O3 Zn1 O1 89.29(11) 6_464 4_564 ? O3 Zn1 O1 91.83(7) . 4_564 ? O1 Zn1 O1 178.32(15) 2_564 4_564 ? O3 Zn1 N1 169.84(10) 6_464 . ? O3 Zn1 N1 93.17(8) . . ? O1 Zn1 N1 91.24(10) 2_564 . ? O1 Zn1 N1 87.44(9) 4_564 . ? O3 Zn1 N1 93.17(8) 6_464 6_464 ? O3 Zn1 N1 169.84(10) . 6_464 ? O1 Zn1 N1 87.44(9) 2_564 6_464 ? O1 Zn1 N1 91.24(10) 4_564 6_464 ? N1 Zn1 N1 77.30(12) . 6_464 ? C6 O1 Zn1 127.4(2) . 3_455 ? C1 C2 C3 119.4(3) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 C6 119.6(2) . . ? C2 C3 C6 122.6(2) . . ? O2 C6 O1 126.5(3) . . ? O2 C6 C3 117.4(2) . . ? O1 C6 C3 116.2(2) . . ? C3 C4 C5 119.9(2) . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C5 116.53(14) . 6_464 ? C4 C5 C5 121.36(14) . 6_464 ? N1 C1 C2 122.1(3) . . ? C5 N1 C1 118.8(2) . . ? C5 N1 Zn1 114.69(17) . . ? C1 N1 Zn1 126.2(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.513 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.064 #==END data_1M-1 _database_code_depnum_ccdc_archive 'CCDC 862099' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(2)2(1) _symmetry_space_group_name_Hall P3(2)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 11.9058(7) _cell_length_b 11.9058(7) _cell_length_c 8.3177(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1021.06(16) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2799 _cell_measurement_theta_min 3.1468 _cell_measurement_theta_max 27.4007 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.833 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9348 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6064 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 23.99 _reflns_number_total 1083 _reflns_number_gt 1052 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.2056P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 1083 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.308 _refine_ls_restrained_S_all 1.308 _refine_ls_shift/su_max 0.219 _refine_ls_shift/su_mean 0.031 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 0.28792(4) 0.0000 0.1667 0.02196(18) Uani 1 2 d S . . O3 O 0.1286(2) -0.0832(3) 0.0134(2) 0.0281(5) Uani 1 1 d . . . H3A H 0.1306 -0.1265 -0.0743 0.034 Uiso 1 1 d R . . H3B H 0.0580 -0.0766 0.0342 0.034 Uiso 1 1 d R . . N1 N 0.3962(3) -0.0638(3) 0.0255(3) 0.0250(8) Uani 1 1 d . . . O2 O 0.6226(3) -0.2042(3) -0.3628(3) 0.0318(6) Uani 1 1 d . . . C5 C 0.4469(4) -0.1485(4) -0.2070(4) 0.0338(8) Uani 1 1 d . . . H5A H 0.4211 -0.1895 -0.3063 0.041 Uiso 1 1 calc R . . C6 C 0.3652(4) -0.1198(4) -0.1197(4) 0.0367(10) Uani 1 1 d . . . H6A H 0.2855 -0.1403 -0.1639 0.044 Uiso 1 1 calc R . . C1 C 0.5132(3) -0.0320(3) 0.0868(4) 0.0202(8) Uani 1 1 d . . . O1 O 0.7706(2) -0.1037(3) -0.1698(3) 0.0362(7) Uani 1 1 d . . . C3 C 0.5665(4) -0.1156(4) -0.1448(4) 0.0248(8) Uani 1 1 d . . . C2 C 0.5995(3) -0.0566(4) 0.0036(4) 0.0270(8) Uani 1 1 d . . . H2A H 0.6799 -0.0332 0.0481 0.032 Uiso 1 1 calc R . . C4 C 0.6619(3) -0.1434(3) -0.2335(4) 0.0244(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 0.0212(2) 0.0292(3) 0.0182(3) 0.0044(3) 0.00219(14) 0.01459(17) O3 0.0211(12) 0.0310(16) 0.0298(13) 0.0016(14) 0.0006(10) 0.0112(14) N1 0.0221(19) 0.037(2) 0.0178(14) -0.0055(13) -0.0015(13) 0.0164(17) O2 0.0269(15) 0.0442(18) 0.0251(14) -0.0165(15) -0.0031(14) 0.0183(12) C5 0.034(2) 0.045(3) 0.0232(18) -0.0132(19) -0.005(2) 0.0202(18) C6 0.023(2) 0.066(3) 0.027(2) -0.014(2) -0.0098(17) 0.027(2) C1 0.0210(18) 0.0234(19) 0.0161(16) -0.0034(14) -0.0027(14) 0.0109(16) O1 0.0267(15) 0.0459(17) 0.0364(16) -0.0221(12) -0.0076(11) 0.0184(13) C3 0.023(2) 0.033(2) 0.0181(18) -0.0044(16) 0.0002(16) 0.0133(16) C2 0.0186(18) 0.040(2) 0.0247(19) -0.0070(17) -0.0050(15) 0.0164(17) C4 0.027(2) 0.0223(18) 0.0225(19) -0.0045(16) 0.0026(17) 0.0109(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.080(2) 4 ? Zn1 O3 2.080(2) . ? Zn1 O2 2.120(2) 2_545 ? Zn1 O2 2.120(2) 5_664 ? Zn1 N1 2.144(3) 4 ? Zn1 N1 2.144(3) . ? N1 C6 1.339(4) . ? N1 C1 1.348(4) . ? O2 C4 1.249(4) . ? O2 Zn1 2.120(2) 3_654 ? C5 C3 1.376(5) . ? C5 C6 1.386(5) . ? C1 C2 1.386(5) . ? C1 C1 1.484(6) 4 ? O1 C4 1.252(4) . ? C3 C2 1.376(5) . ? C3 C4 1.523(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 95.28(16) 4 . ? O3 Zn1 O2 91.64(8) 4 2_545 ? O3 Zn1 O2 89.61(13) . 2_545 ? O3 Zn1 O2 89.61(13) 4 5_664 ? O3 Zn1 O2 91.64(8) . 5_664 ? O2 Zn1 O2 178.15(18) 2_545 5_664 ? O3 Zn1 N1 93.56(10) 4 4 ? O3 Zn1 N1 170.68(13) . 4 ? O2 Zn1 N1 87.20(10) 2_545 4 ? O2 Zn1 N1 91.36(12) 5_664 4 ? O3 Zn1 N1 170.68(13) 4 . ? O3 Zn1 N1 93.56(10) . . ? O2 Zn1 N1 91.36(12) 2_545 . ? O2 Zn1 N1 87.20(10) 5_664 . ? N1 Zn1 N1 77.77(15) 4 . ? C6 N1 C1 118.0(3) . . ? C6 N1 Zn1 127.3(2) . . ? C1 N1 Zn1 114.4(2) . . ? C4 O2 Zn1 127.2(2) . 3_654 ? C3 C5 C6 119.1(3) . . ? N1 C6 C5 122.9(3) . . ? N1 C1 C2 121.5(3) . . ? N1 C1 C1 116.55(18) . 4 ? C2 C1 C1 121.92(19) . 4 ? C2 C3 C5 118.2(3) . . ? C2 C3 C4 119.5(3) . . ? C5 C3 C4 122.3(3) . . ? C3 C2 C1 120.2(3) . . ? O1 C4 O2 126.9(3) . . ? O1 C4 C3 117.1(3) . . ? O2 C4 C3 116.0(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.262 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.055 #==END data_1P-2 _database_code_depnum_ccdc_archive 'CCDC 870420' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 11.8429(11) _cell_length_b 11.8429(11) _cell_length_c 8.2715(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1004.7(2) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2439 _cell_measurement_theta_min 3.1640 _cell_measurement_theta_max 27.4856 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.863 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8399 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6403 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1190 _reflns_number_gt 1129 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.6617P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 1190 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.71216(6) 0.71216(6) 0.0000 0.0246(2) Uani 1 2 d S . . O1 O 0.8716(3) 0.7884(4) -0.1533(3) 0.0311(7) Uani 1 1 d . . . H5B H 0.8702 0.7437 -0.2420 0.037 Uiso 1 1 d R . . H5C H 0.9422 0.8662 -0.1314 0.037 Uiso 1 1 d R . . O2 O 0.3777(4) 0.1734(3) -0.5295(4) 0.0327(8) Uani 1 1 d . . . N1 N 0.6036(4) 0.5398(4) -0.1411(4) 0.0275(10) Uani 1 1 d . . . C4 C 0.5523(6) 0.4049(5) -0.3737(6) 0.0385(12) Uani 1 1 d . . . H4A H 0.5788 0.3899 -0.4774 0.046 Uiso 1 1 d R . . C5 C 0.6345(5) 0.5150(5) -0.2853(6) 0.0416(14) Uani 1 1 d . . . H5A H 0.7151 0.5742 -0.3291 0.050 Uiso 1 1 calc R . . C3 C 0.4339(5) 0.3174(5) -0.3116(5) 0.0265(10) Uani 1 1 d . . . C6 C 0.3386(5) 0.1943(5) -0.3986(6) 0.0258(10) Uani 1 1 d . . . O3 O 0.2295(3) 0.1262(3) -0.3367(4) 0.0386(10) Uani 1 1 d . . . C2 C 0.4002(5) 0.3435(5) -0.1622(5) 0.0286(10) Uani 1 1 d . . . H2A H 0.3193 0.2863 -0.1175 0.034 Uiso 1 1 calc R . . C1 C 0.4866(4) 0.4546(4) -0.0796(5) 0.0233(10) 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 0.0245(3) 0.0245(3) 0.0194(3) 0.00246(17) -0.00246(17) 0.0083(4) O1 0.0239(16) 0.034(2) 0.0316(16) 0.0025(19) 0.0003(13) 0.0118(19) O2 0.027(2) 0.0364(19) 0.0251(16) -0.0136(15) 0.0020(18) 0.0090(17) N1 0.024(2) 0.029(2) 0.0187(17) -0.0047(16) 0.0010(17) 0.0052(19) C4 0.041(3) 0.047(3) 0.023(2) -0.010(2) 0.005(2) 0.018(3) C5 0.027(3) 0.038(3) 0.031(3) -0.005(2) 0.014(2) -0.006(2) C3 0.025(3) 0.030(2) 0.022(2) -0.0029(19) -0.001(2) 0.012(2) C6 0.024(2) 0.030(2) 0.025(2) -0.007(2) 0.000(2) 0.015(2) O3 0.033(2) 0.036(2) 0.038(2) -0.0151(15) 0.0072(15) 0.0098(17) C2 0.021(2) 0.032(3) 0.024(2) -0.005(2) 0.0025(19) 0.007(2) C1 0.023(2) 0.026(2) 0.021(2) 0.0001(19) -0.0003(18) 0.0119(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.070(3) 4 ? Zn1 O1 2.070(3) . ? Zn1 O2 2.110(3) 6_664 ? Zn1 O2 2.110(3) 3_665 ? Zn1 N1 2.135(4) . ? Zn1 N1 2.135(4) 4 ? O2 C6 1.250(6) . ? O2 Zn1 2.110(3) 2_654 ? N1 C5 1.322(6) . ? N1 C1 1.342(5) . ? C4 C3 1.360(6) . ? C4 C5 1.383(7) . ? C3 C2 1.380(6) . ? C3 C6 1.507(6) . ? C6 O3 1.241(6) . ? C2 C1 1.378(6) . ? C1 C1 1.472(8) 4 ? 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 95.2(2) 4 . ? O1 Zn1 O2 89.67(18) 4 6_664 ? O1 Zn1 O2 91.72(11) . 6_664 ? O1 Zn1 O2 91.72(11) 4 3_665 ? O1 Zn1 O2 89.67(18) . 3_665 ? O2 Zn1 O2 177.9(2) 6_664 3_665 ? O1 Zn1 N1 170.68(18) 4 . ? O1 Zn1 N1 93.66(13) . . ? O2 Zn1 N1 87.16(13) 6_664 . ? O2 Zn1 N1 91.23(16) 3_665 . ? O1 Zn1 N1 93.66(13) 4 4 ? O1 Zn1 N1 170.68(18) . 4 ? O2 Zn1 N1 91.23(16) 6_664 4 ? O2 Zn1 N1 87.16(13) 3_665 4 ? N1 Zn1 N1 77.7(2) . 4 ? C6 O2 Zn1 127.0(3) . 2_654 ? C5 N1 C1 118.1(4) . . ? C5 N1 Zn1 127.2(3) . . ? C1 N1 Zn1 114.4(3) . . ? C3 C4 C5 119.4(4) . . ? N1 C5 C4 122.9(5) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 C6 123.0(4) . . ? C2 C3 C6 118.9(4) . . ? O3 C6 O2 126.7(4) . . ? O3 C6 C3 117.7(4) . . ? O2 C6 C3 115.7(4) . . ? C3 C2 C1 119.8(4) . . ? N1 C1 C2 121.7(4) . . ? N1 C1 C1 116.6(2) . 4 ? C2 C1 C1 121.7(3) . 4 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.663 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.087 #==END data_1P-4 _database_code_depnum_ccdc_archive 'CCDC 870421' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 11.9194(6) _cell_length_b 11.9194(6) _cell_length_c 8.3261(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1024.43(15) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2895 _cell_measurement_theta_min 3.1434 _cell_measurement_theta_max 27.4585 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.827 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9362 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number 1571 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7582 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1571 _reflns_number_gt 1506 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.3058P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.025(19) _refine_ls_number_reflns 1571 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.71209(3) 0.71209(3) 0.0000 0.02234(13) Uani 1 2 d S . . O1 O 0.7875(2) 0.87121(17) 0.1539(2) 0.0286(4) Uani 1 1 d . . . H2B H 0.7422 0.8690 0.2415 0.034 Uiso 1 1 d R . . H2C H 0.8647 0.9418 0.1333 0.034 Uiso 1 1 d R . . O2 O 0.1732(2) 0.3776(3) 0.5297(2) 0.0327(5) Uani 1 1 d . . . N1 N 0.5399(2) 0.6037(2) 0.1411(3) 0.0253(6) Uani 1 1 d . . . C2 C 0.4047(3) 0.5533(4) 0.3737(3) 0.0356(7) Uani 1 1 d . . . H2A H 0.3891 0.5797 0.4763 0.043 Uiso 1 1 d R . . C1 C 0.5150(3) 0.6353(3) 0.2863(3) 0.0381(8) Uani 1 1 d . . . H1A H 0.5755 0.7181 0.3310 0.046 Uiso 1 1 d R . . C3 C 0.3176(3) 0.4336(3) 0.3117(3) 0.0247(6) Uani 1 1 d . . . O3 O 0.1259(2) 0.2296(2) 0.3367(3) 0.0367(6) Uani 1 1 d . . . C6 C 0.1949(3) 0.3385(3) 0.3998(4) 0.0246(6) Uani 1 1 d . . . C4 C 0.3435(3) 0.4001(3) 0.1623(3) 0.0260(6) Uani 1 1 d . . . H4A H 0.2841 0.3178 0.1156 0.031 Uiso 1 1 d R . . C5 C 0.4550(3) 0.4869(2) 0.0800(3) 0.0214(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02169(17) 0.02169(17) 0.0184(2) 0.00230(9) -0.00230(9) 0.0069(2) O1 0.0306(12) 0.0225(9) 0.0302(10) 0.0004(8) -0.0045(11) 0.0114(11) O2 0.0337(11) 0.0294(12) 0.0266(11) -0.0018(11) 0.0146(9) 0.0095(11) N1 0.0262(12) 0.0210(13) 0.0194(11) -0.0019(10) 0.0029(9) 0.0048(10) C2 0.0391(16) 0.0315(17) 0.0247(14) -0.0046(14) 0.0102(12) 0.0088(16) C1 0.0381(17) 0.0255(16) 0.0285(16) -0.0091(13) 0.0060(13) -0.0006(13) C3 0.0278(14) 0.0258(15) 0.0189(13) 0.0010(12) 0.0051(11) 0.0121(12) O3 0.0342(12) 0.0279(11) 0.0370(13) -0.0066(9) 0.0139(9) 0.0074(9) C6 0.0235(14) 0.0239(14) 0.0251(14) 0.0017(12) 0.0058(12) 0.0108(12) C4 0.0283(14) 0.0209(13) 0.0215(14) -0.0025(11) 0.0046(11) 0.0068(12) C5 0.0240(13) 0.0213(13) 0.0165(13) -0.0024(10) 0.0008(11) 0.0095(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.0841(18) . ? Zn1 O1 2.0841(18) 4 ? Zn1 O2 2.1208(19) 2_664 ? Zn1 O2 2.1208(19) 5_665 ? Zn1 N1 2.148(2) 4 ? Zn1 N1 2.148(2) . ? O2 C6 1.255(4) . ? O2 Zn1 2.1208(19) 3_565 ? N1 C1 1.342(4) . ? N1 C5 1.346(3) . ? C2 C3 1.378(4) . ? C2 C1 1.388(4) . ? C3 C4 1.388(4) . ? C3 C6 1.518(4) . ? O3 C6 1.254(4) . ? C4 C5 1.389(4) . ? C5 C5 1.486(5) 4 ? 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 95.74(13) . 4 ? O1 Zn1 O2 89.59(11) . 2_664 ? O1 Zn1 O2 91.73(7) 4 2_664 ? O1 Zn1 O2 91.73(7) . 5_665 ? O1 Zn1 O2 89.59(11) 4 5_665 ? O2 Zn1 O2 178.03(16) 2_664 5_665 ? O1 Zn1 N1 170.42(11) . 4 ? O1 Zn1 N1 93.37(8) 4 4 ? O2 Zn1 N1 87.19(9) 2_664 4 ? O2 Zn1 N1 91.28(10) 5_665 4 ? O1 Zn1 N1 93.37(8) . . ? O1 Zn1 N1 170.42(11) 4 . ? O2 Zn1 N1 91.28(10) 2_664 . ? O2 Zn1 N1 87.19(9) 5_665 . ? N1 Zn1 N1 77.69(12) 4 . ? C6 O2 Zn1 127.3(2) . 3_565 ? C1 N1 C5 118.2(3) . . ? C1 N1 Zn1 127.1(2) . . ? C5 N1 Zn1 114.42(18) . . ? C3 C2 C1 119.4(3) . . ? N1 C1 C2 122.6(3) . . ? C2 C3 C4 118.2(3) . . ? C2 C3 C6 122.6(3) . . ? C4 C3 C6 119.2(3) . . ? O3 C6 O2 126.5(3) . . ? O3 C6 C3 117.4(2) . . ? O2 C6 C3 116.1(3) . . ? C3 C4 C5 119.7(3) . . ? N1 C5 C4 121.9(2) . . ? N1 C5 C5 116.58(15) . 4 ? C4 C5 C5 121.56(15) . 4 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.331 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.059 #==END data_1P-5 _database_code_depnum_ccdc_archive 'CCDC 870422' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 11.9329(13) _cell_length_b 11.9329(13) _cell_length_c 8.3384(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1028.3(3) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3019 _cell_measurement_theta_min 3.1392 _cell_measurement_theta_max 27.4161 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.820 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9120 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8033 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.42 _reflns_number_total 1569 _reflns_number_gt 1486 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.2406P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.002(19) _refine_ls_number_reflns 1569 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.28790(4) 0.0000 0.8333 0.02210(13) Uani 1 2 d S . . O1 O 0.2120(3) 0.0834(3) 0.6796(2) 0.0290(4) Uani 1 1 d . . . H4B H 0.2566 0.1266 0.5918 0.035 Uiso 1 1 d R . . H4C H 0.1348 0.0764 0.7010 0.035 Uiso 1 1 d R . . O3 O 0.8271(2) 0.2047(3) 0.3037(2) 0.0323(5) Uani 1 1 d . . . N1 N 0.4598(2) 0.0638(2) 0.6922(3) 0.0257(6) Uani 1 1 d . . . C4 C 0.5950(3) 0.1483(4) 0.4599(4) 0.0337(7) Uani 1 1 d . . . H4A H 0.6099 0.1907 0.3579 0.040 Uiso 1 1 d R . . C5 C 0.4854(3) 0.1206(3) 0.5473(4) 0.0379(9) Uani 1 1 d . . . H5A H 0.4203 0.1328 0.4958 0.045 Uiso 1 1 d R . . C3 C 0.6829(3) 0.1163(3) 0.5219(3) 0.0253(6) Uani 1 1 d . . . O2 O 0.8741(2) 0.1035(2) 0.4966(2) 0.0357(6) Uani 1 1 d . . . C6 C 0.8055(3) 0.1438(3) 0.4334(4) 0.0241(6) Uani 1 1 d . . . C2 C 0.6565(3) 0.0569(3) 0.6710(3) 0.0264(6) Uani 1 1 d . . . H2A H 0.7141 0.0306 0.7152 0.032 Uiso 1 1 d R . . C1 C 0.5449(3) 0.0318(3) 0.7533(3) 0.0214(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02143(17) 0.0289(3) 0.0185(2) -0.0044(2) -0.00218(10) 0.01444(13) O1 0.0306(13) 0.0301(13) 0.0310(11) -0.0029(12) -0.0019(12) 0.0187(9) O3 0.0339(12) 0.0449(14) 0.0248(11) 0.0167(12) 0.0138(10) 0.0246(12) N1 0.0267(12) 0.0392(16) 0.0195(11) 0.0053(11) 0.0032(10) 0.0227(11) C4 0.0376(16) 0.050(2) 0.0242(15) 0.0154(16) 0.0094(12) 0.0294(18) C5 0.0393(18) 0.065(3) 0.0276(16) 0.0155(16) 0.0062(14) 0.0402(18) C3 0.0289(14) 0.0289(15) 0.0228(14) 0.0034(12) 0.0054(12) 0.0179(13) O2 0.0340(12) 0.0462(14) 0.0352(13) 0.0209(10) 0.0142(9) 0.0263(11) C6 0.0257(15) 0.0225(14) 0.0243(15) 0.0035(12) 0.0054(12) 0.0123(12) C2 0.0265(15) 0.0345(16) 0.0242(15) 0.0078(13) 0.0042(12) 0.0197(13) C1 0.0243(14) 0.0251(15) 0.0172(14) 0.0027(11) -0.0010(11) 0.0143(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 2.0871(19) . ? Zn1 O1 2.0871(19) 5_556 ? Zn1 O3 2.121(2) 4_546 ? Zn1 O3 2.121(2) 3_665 ? Zn1 N1 2.147(2) . ? Zn1 N1 2.147(2) 5_556 ? O3 C6 1.255(4) . ? O3 Zn1 2.121(2) 2_654 ? N1 C5 1.344(4) . ? N1 C1 1.351(3) . ? C4 C3 1.383(4) . ? C4 C5 1.385(4) . ? C3 C2 1.387(4) . ? C3 C6 1.521(4) . ? O2 C6 1.254(4) . ? C2 C1 1.391(4) . ? C1 C1 1.488(5) 5_556 ? 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 95.50(14) . 5_556 ? O1 Zn1 O3 91.66(7) . 4_546 ? O1 Zn1 O3 89.75(12) 5_556 4_546 ? O1 Zn1 O3 89.75(12) . 3_665 ? O1 Zn1 O3 91.66(7) 5_556 3_665 ? O3 Zn1 O3 177.91(16) 4_546 3_665 ? O1 Zn1 N1 93.43(9) . . ? O1 Zn1 N1 170.61(11) 5_556 . ? O3 Zn1 N1 87.09(9) 4_546 . ? O3 Zn1 N1 91.28(11) 3_665 . ? O1 Zn1 N1 170.61(11) . 5_556 ? O1 Zn1 N1 93.43(9) 5_556 5_556 ? O3 Zn1 N1 91.28(10) 4_546 5_556 ? O3 Zn1 N1 87.09(9) 3_665 5_556 ? N1 Zn1 N1 77.82(13) . 5_556 ? C6 O3 Zn1 127.2(2) . 2_654 ? C5 N1 C1 117.9(3) . . ? C5 N1 Zn1 127.4(2) . . ? C1 N1 Zn1 114.40(18) . . ? C3 C4 C5 119.6(3) . . ? N1 C5 C4 122.9(3) . . ? C4 C3 C2 117.8(3) . . ? C4 C3 C6 122.6(3) . . ? C2 C3 C6 119.6(3) . . ? O2 C6 O3 126.8(3) . . ? O2 C6 C3 117.1(3) . . ? O3 C6 C3 116.1(3) . . ? C3 C2 C1 120.0(3) . . ? N1 C1 C2 121.8(2) . . ? N1 C1 C1 116.52(16) . 5_556 ? C2 C1 C1 121.67(16) . 5_556 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.306 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.061 #==END data_1P-6 _database_code_depnum_ccdc_archive 'CCDC 870423' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 11.9072(5) _cell_length_b 11.9072(5) _cell_length_c 8.3161(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1021.10(10) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3594 _cell_measurement_theta_min 2.4492 _cell_measurement_theta_max 27.4353 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.833 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8443 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn724+ (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6666 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 23.99 _reflns_number_total 1083 _reflns_number_gt 1066 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0440P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(19) _refine_ls_number_reflns 1083 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 1.0000 0.28792(4) 0.1667 0.02238(17) Uani 1 2 d S . . O3 O 0.9167(3) 0.12841(18) 0.0127(2) 0.0295(5) Uani 1 1 d . . . H3B H 0.8735 0.1305 -0.0750 0.035 Uiso 1 1 d R . . H3C H 0.9234 0.0578 0.0334 0.035 Uiso 1 1 d R . . O1 O 0.7960(3) 0.6228(3) -0.3630(2) 0.0330(5) Uani 1 1 d . . . N1 N 0.9360(3) 0.3964(2) 0.0257(3) 0.0254(7) Uani 1 1 d . . . C3 C 0.8517(4) 0.4468(4) -0.2069(4) 0.0342(8) Uani 1 1 d . . . H3A H 0.8100 0.4204 -0.3098 0.041 Uiso 1 1 d R . . C2 C 0.8841(3) 0.5665(3) -0.1451(4) 0.0254(7) Uani 1 1 d . . . C5 C 0.9686(3) 0.5129(3) 0.0864(3) 0.0219(7) Uani 1 1 d . . . C6 C 0.9429(3) 0.5989(3) 0.0041(3) 0.0265(7) Uani 1 1 d . . . H6A H 0.9655 0.6810 0.0514 0.032 Uiso 1 1 d R . . C4 C 0.8798(3) 0.3654(3) -0.1201(4) 0.0382(9) Uani 1 1 d . . . H4A H 0.8574 0.2823 -0.1647 0.046 Uiso 1 1 d R . . O2 O 0.8965(2) 0.7706(2) -0.1699(3) 0.0364(7) Uani 1 1 d . . . C1 C 0.8561(3) 0.6616(3) -0.2336(4) 0.0244(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 Zn1 0.0301(3) 0.0222(2) 0.0175(2) 0.00221(12) 0.0044(2) 0.01503(16) O3 0.0325(15) 0.0238(11) 0.0320(11) 0.0013(9) 0.0017(13) 0.0138(13) O1 0.0455(16) 0.0294(14) 0.0266(12) -0.0042(13) -0.0183(13) 0.0206(11) N1 0.0391(18) 0.0211(16) 0.0179(12) -0.0007(12) -0.0039(12) 0.0165(15) C3 0.047(2) 0.035(2) 0.0225(14) -0.0042(18) -0.0140(18) 0.0216(16) C2 0.0311(18) 0.0212(18) 0.0216(14) 0.0001(15) -0.0030(14) 0.0113(14) C5 0.0262(18) 0.0222(17) 0.0150(14) -0.0037(13) -0.0029(13) 0.0105(15) C6 0.0391(19) 0.0192(16) 0.0233(15) -0.0031(14) -0.0073(15) 0.0161(15) C4 0.068(3) 0.025(2) 0.0265(16) -0.0092(15) -0.0110(18) 0.027(2) O2 0.0463(15) 0.0287(13) 0.0354(14) -0.0067(10) -0.0226(11) 0.0196(11) C1 0.0251(17) 0.0242(18) 0.0218(15) 0.0016(15) -0.0038(14) 0.0108(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.0851(19) 6_765 ? Zn1 O3 2.0851(19) . ? Zn1 O1 2.119(2) 3_665 ? Zn1 O1 2.119(2) 5_664 ? Zn1 N1 2.146(2) 6_765 ? Zn1 N1 2.146(2) . ? O1 C1 1.246(4) . ? O1 Zn1 2.119(2) 2_654 ? N1 C5 1.339(3) . ? N1 C4 1.344(4) . ? C3 C2 1.376(4) . ? C3 C4 1.378(4) . ? C2 C6 1.382(4) . ? C2 C1 1.520(4) . ? C5 C6 1.386(4) . ? C5 C5 1.484(5) 6_765 ? O2 C1 1.254(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 95.38(13) 6_765 . ? O3 Zn1 O1 91.54(8) 6_765 3_665 ? O3 Zn1 O1 89.62(12) . 3_665 ? O3 Zn1 O1 89.62(12) 6_765 5_664 ? O3 Zn1 O1 91.54(8) . 5_664 ? O1 Zn1 O1 178.27(16) 3_665 5_664 ? O3 Zn1 N1 93.58(8) 6_765 6_765 ? O3 Zn1 N1 170.62(11) . 6_765 ? O1 Zn1 N1 87.35(9) 3_665 6_765 ? O1 Zn1 N1 91.31(11) 5_664 6_765 ? O3 Zn1 N1 170.62(12) 6_765 . ? O3 Zn1 N1 93.58(8) . . ? O1 Zn1 N1 91.31(11) 3_665 . ? O1 Zn1 N1 87.35(9) 5_664 . ? N1 Zn1 N1 77.63(13) 6_765 . ? C1 O1 Zn1 127.3(2) . 2_654 ? C5 N1 C4 118.1(3) . . ? C5 N1 Zn1 114.31(19) . . ? C4 N1 Zn1 127.2(2) . . ? C2 C3 C4 119.5(3) . . ? C3 C2 C6 117.7(3) . . ? C3 C2 C1 122.5(3) . . ? C6 C2 C1 119.7(3) . . ? N1 C5 C6 121.5(3) . . ? N1 C5 C5 116.65(16) . 6_765 ? C6 C5 C5 121.84(16) . 6_765 ? C2 C6 C5 120.4(3) . . ? N1 C4 C3 122.8(3) . . ? O1 C1 O2 126.9(3) . . ? O1 C1 C2 116.2(3) . . ? O2 C1 C2 116.9(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.281 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.054 #==END data_1M-2 _database_code_depnum_ccdc_archive 'CCDC 870424' #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(2)2(1) _symmetry_space_group_name_Hall P3(2)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 11.9175(6) _cell_length_b 11.9175(6) _cell_length_c 8.3253(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1024.00(18) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3103 _cell_measurement_theta_min 3.1438 _cell_measurement_theta_max 27.4624 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.828 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7113 _exptl_absorpt_correction_T_max 0.7711 _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 ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8009 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1568 _reflns_number_gt 1508 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.1011P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(14) _refine_ls_number_reflns 1568 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.045 _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 0.28791(3) 0.3333 0.02135(10) Uani 1 2 d S . . O3 O -0.08498(19) 0.12867(13) 0.48915(17) 0.0285(3) Uani 1 1 d . . . N1 N -0.06437(18) 0.39613(17) 0.4742(2) 0.0252(4) Uani 1 1 d . . . O2 O -0.2045(2) 0.62253(19) 0.86305(18) 0.0314(4) Uani 1 1 d . . . C2 C -0.1487(3) 0.4463(3) 0.7068(3) 0.0340(5) Uani 1 1 d . . . H2 H -0.1892 0.4209 0.8063 0.041 Uiso 1 1 calc R . . C1 C -0.1208(3) 0.3644(2) 0.6195(3) 0.0370(6) Uani 1 1 d . . . H1 H -0.1418 0.2844 0.6632 0.044 Uiso 1 1 calc R . . C6 C -0.03247(19) 0.51252(18) 0.4135(2) 0.0209(4) Uani 1 1 d . . . O1 O -0.10327(17) 0.77058(15) 0.66991(19) 0.0354(4) Uani 1 1 d . . . C3 C -0.1157(2) 0.5663(2) 0.6442(3) 0.0241(4) Uani 1 1 d . . . C5 C -0.0578(2) 0.5991(2) 0.4957(2) 0.0253(4) Uani 1 1 d . . . H5 H -0.0356 0.6789 0.4503 0.030 Uiso 1 1 calc R . . C4 C -0.1436(2) 0.6615(2) 0.7341(3) 0.0243(5) Uani 1 1 d . . . H3 H -0.0101 0.1364 0.4850 0.029 Uiso 1 1 d R . . H3' H -0.1315 0.0651 0.4301 0.029 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0285(2) 0.02079(13) 0.01733(16) -0.00217(7) -0.00435(14) 0.01425(10) O3 0.0245(9) 0.0217(7) 0.0329(8) -0.0020(6) -0.0090(8) 0.0067(7) N1 0.0357(11) 0.0215(10) 0.0195(9) 0.0001(7) 0.0044(7) 0.0152(9) O2 0.0446(10) 0.0273(9) 0.0241(8) 0.0030(8) 0.0164(8) 0.0194(7) C2 0.0518(16) 0.0307(13) 0.0221(11) 0.0050(10) 0.0149(11) 0.0226(11) C1 0.0621(18) 0.0244(12) 0.0262(12) 0.0095(9) 0.0138(11) 0.0228(13) C6 0.0261(11) 0.0213(10) 0.0158(10) 0.0008(7) 0.0014(8) 0.0121(9) O1 0.0472(10) 0.0272(8) 0.0357(10) 0.0074(7) 0.0211(7) 0.0216(8) C3 0.0277(11) 0.0211(11) 0.0217(10) -0.0005(9) 0.0046(9) 0.0110(9) C5 0.0356(12) 0.0207(10) 0.0237(11) 0.0033(8) 0.0061(9) 0.0171(9) C4 0.0248(10) 0.0248(11) 0.0230(11) -0.0030(9) 0.0026(8) 0.0123(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.0948(14) 5 ? Zn1 O3 2.0948(14) . ? Zn1 O2 2.1182(14) 3_454 ? Zn1 O2 2.1182(14) 4_666 ? Zn1 N1 2.1485(17) 5 ? Zn1 N1 2.1485(17) . ? N1 C6 1.340(3) . ? N1 C1 1.344(3) . ? O2 C4 1.248(3) . ? O2 Zn1 2.1182(14) 2_565 ? C2 C3 1.382(3) . ? C2 C1 1.384(3) . ? C6 C5 1.391(3) . ? C6 C6 1.494(4) 5 ? O1 C4 1.258(3) . ? C3 C5 1.374(3) . ? C3 C4 1.527(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 96.76(10) 5 . ? O3 Zn1 O2 91.78(5) 5 3_454 ? O3 Zn1 O2 89.55(8) . 3_454 ? O3 Zn1 O2 89.55(8) 5 4_666 ? O3 Zn1 O2 91.78(5) . 4_666 ? O2 Zn1 O2 178.00(12) 3_454 4_666 ? O3 Zn1 N1 92.86(6) 5 5 ? O3 Zn1 N1 169.98(8) . 5 ? O2 Zn1 N1 87.32(6) 3_454 5 ? O2 Zn1 N1 91.12(8) 4_666 5 ? O3 Zn1 N1 169.98(8) 5 . ? O3 Zn1 N1 92.86(6) . . ? O2 Zn1 N1 91.12(8) 3_454 . ? O2 Zn1 N1 87.32(6) 4_666 . ? N1 Zn1 N1 77.70(9) 5 . ? C6 N1 C1 118.28(19) . . ? C6 N1 Zn1 114.45(14) . . ? C1 N1 Zn1 126.96(16) . . ? C4 O2 Zn1 127.44(15) . 2_565 ? C3 C2 C1 119.2(2) . . ? N1 C1 C2 122.5(2) . . ? N1 C6 C5 121.85(19) . . ? N1 C6 C6 116.56(11) . 5 ? C5 C6 C6 121.59(12) . 5 ? C5 C3 C2 118.4(2) . . ? C5 C3 C4 119.66(19) . . ? C2 C3 C4 121.94(19) . . ? C3 C5 C6 119.76(19) . . ? O2 C4 O1 126.9(2) . . ? O2 C4 C3 116.58(19) . . ? O1 C4 C3 116.54(19) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.291 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.051 #==END data_1M-3 _database_code_depnum_ccdc_archive 'CCDC 870425' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(2)2(1) _symmetry_space_group_name_Hall P3(2)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 11.9166(4) _cell_length_b 11.9166(4) _cell_length_c 8.3263(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1023.97(7) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2976 _cell_measurement_theta_min 3.1437 _cell_measurement_theta_max 27.4584 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.828 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9367 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 (4x4 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8151 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1566 _reflns_number_gt 1464 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(15) _refine_ls_number_reflns 1566 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0600 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.28795(3) 0.0000 0.1667 0.02145(11) Uani 1 2 d S . . O3 O 0.12899(14) -0.0848(2) 0.01195(18) 0.0287(4) Uani 1 1 d . . . N1 N 0.39654(18) -0.06395(19) 0.0262(2) 0.0242(5) Uani 1 1 d . . . O2 O 0.6226(2) -0.2041(2) -0.36278(19) 0.0319(4) Uani 1 1 d . . . C4 C 0.4465(3) -0.1490(3) -0.2066(3) 0.0339(5) Uani 1 1 d . . . H4 H 0.4207 -0.1901 -0.3057 0.041 Uiso 1 1 calc R . . C5 C 0.3644(2) -0.1203(3) -0.1194(3) 0.0366(7) Uani 1 1 d . . . H5 H 0.2847 -0.1408 -0.1632 0.044 Uiso 1 1 calc R . . C6 C 0.6614(2) -0.1431(2) -0.2329(3) 0.0243(5) Uani 1 1 d . . . C2 C 0.5991(2) -0.0577(2) 0.0048(3) 0.0244(5) Uani 1 1 d . . . H2 H 0.6787 -0.0356 0.0505 0.029 Uiso 1 1 calc R . . C1 C 0.5126(2) -0.0322(2) 0.0866(3) 0.0207(5) Uani 1 1 d . . . O1 O 0.77043(16) -0.10352(19) -0.1696(2) 0.0355(5) Uani 1 1 d . . . C3 C 0.5667(2) -0.1159(2) -0.1444(3) 0.0241(5) Uani 1 1 d . . . H3' H 0.0522 -0.1279 0.0492 0.029 Uiso 1 1 d R . . H3'' H 0.1282 -0.0186 -0.0340 0.029 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02081(14) 0.0288(2) 0.01742(17) 0.00447(17) 0.00223(8) 0.01440(11) O3 0.0214(7) 0.0256(10) 0.0325(9) 0.0099(9) 0.0021(6) 0.0068(8) N1 0.0201(11) 0.0356(12) 0.0174(9) -0.0042(8) 0.0004(8) 0.0142(10) O2 0.0281(10) 0.0446(11) 0.0255(9) -0.0162(9) -0.0042(9) 0.0201(8) C4 0.0302(14) 0.0493(17) 0.0235(11) -0.0154(13) -0.0052(12) 0.0209(11) C5 0.0245(13) 0.0593(19) 0.0277(13) -0.0145(12) -0.0096(11) 0.0222(14) C6 0.0265(12) 0.0259(12) 0.0213(12) -0.0039(10) 0.0034(10) 0.0137(10) C2 0.0202(11) 0.0348(13) 0.0216(12) -0.0054(10) -0.0029(9) 0.0163(10) C1 0.0232(11) 0.0259(12) 0.0146(11) -0.0010(9) -0.0018(9) 0.0136(10) O1 0.0270(9) 0.0465(11) 0.0369(11) -0.0210(8) -0.0072(7) 0.0212(8) C3 0.0230(12) 0.0283(12) 0.0203(11) -0.0038(10) 0.0011(10) 0.0122(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.0867(15) 4 ? Zn1 O3 2.0867(15) . ? Zn1 O2 2.1222(16) 2_545 ? Zn1 O2 2.1222(16) 5_664 ? Zn1 N1 2.1470(18) 4 ? Zn1 N1 2.1470(18) . ? N1 C1 1.336(3) . ? N1 C5 1.345(3) . ? O2 C6 1.255(3) . ? O2 Zn1 2.1222(16) 3_654 ? C4 C3 1.382(3) . ? C4 C5 1.391(3) . ? C6 O1 1.255(3) . ? C6 C3 1.513(3) . ? C2 C3 1.380(3) . ? C2 C1 1.390(3) . ? C1 C1 1.490(4) 4 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 96.53(11) 4 . ? O3 Zn1 O2 91.80(6) 4 2_545 ? O3 Zn1 O2 89.41(9) . 2_545 ? O3 Zn1 O2 89.41(9) 4 5_664 ? O3 Zn1 O2 91.80(6) . 5_664 ? O2 Zn1 O2 178.19(13) 2_545 5_664 ? O3 Zn1 N1 93.11(7) 4 4 ? O3 Zn1 N1 169.92(9) . 4 ? O2 Zn1 N1 87.33(7) 2_545 4 ? O2 Zn1 N1 91.26(8) 5_664 4 ? O3 Zn1 N1 169.92(9) 4 . ? O3 Zn1 N1 93.11(7) . . ? O2 Zn1 N1 91.26(8) 2_545 . ? O2 Zn1 N1 87.33(7) 5_664 . ? N1 Zn1 N1 77.44(10) 4 . ? C1 N1 C5 118.4(2) . . ? C1 N1 Zn1 114.63(14) . . ? C5 N1 Zn1 126.64(17) . . ? C6 O2 Zn1 127.59(16) . 3_654 ? C3 C4 C5 119.3(2) . . ? N1 C5 C4 122.3(2) . . ? O1 C6 O2 126.3(2) . . ? O1 C6 C3 117.2(2) . . ? O2 C6 C3 116.4(2) . . ? C3 C2 C1 119.9(2) . . ? N1 C1 C2 122.0(2) . . ? N1 C1 C1 116.50(12) . 4 ? C2 C1 C1 121.52(12) . 4 ? C2 C3 C4 118.1(2) . . ? C2 C3 C6 119.6(2) . . ? C4 C3 C6 122.3(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.322 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.097 #==END data_1M-4 _database_code_depnum_ccdc_archive 'CCDC 870426' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(2)2(1) _symmetry_space_group_name_Hall P3(2)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 11.9118(4) _cell_length_b 11.9118(4) _cell_length_c 8.3260(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1023.11(8) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2943 _cell_measurement_theta_min 3.1443 _cell_measurement_theta_max 27.4662 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.829 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9324 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Saturn70 (4x4 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8173 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1567 _reflns_number_gt 1450 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(14) _refine_ls_number_reflns 1567 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0520 _refine_ls_wR_factor_gt 0.0508 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.102 _refine_ls_shift/su_mean 0.005 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 0.71209(3) 0.0000 0.1667 0.02137(10) Uani 1 2 d S . . N1 N 0.60338(16) 0.06381(17) 0.0263(2) 0.0237(4) Uani 1 1 d . . . C2 C 0.5536(3) 0.1489(3) -0.2067(3) 0.0341(5) Uani 1 1 d . . . H2 H 0.5791 0.1893 -0.3062 0.041 Uiso 1 1 calc R . . C3 C 0.4337(2) 0.1165(2) -0.1442(3) 0.0240(5) Uani 1 1 d . . . C6 C 0.48724(19) 0.03210(19) 0.0867(2) 0.0205(4) Uani 1 1 d . . . C1 C 0.6357(2) 0.1204(2) -0.1194(3) 0.0357(6) Uani 1 1 d . . . H1 H 0.7157 0.1412 -0.1631 0.043 Uiso 1 1 calc R . . C5 C 0.4010(2) 0.0575(2) 0.0048(2) 0.0247(5) Uani 1 1 d . . . H5 H 0.3211 0.0349 0.0502 0.030 Uiso 1 1 calc R . . O3 O 0.87085(13) 0.08473(19) 0.01226(16) 0.0284(3) Uani 1 1 d . . . O1 O 0.37713(18) 0.2041(2) -0.36264(18) 0.0317(4) Uani 1 1 d . . . O2 O 0.22946(14) 0.10344(17) -0.16934(19) 0.0359(4) Uani 1 1 d . . . C4 C 0.3388(2) 0.1434(2) -0.2330(3) 0.0239(5) Uani 1 1 d . . . H3'' H 0.9466 0.1210 0.0510 0.029 Uiso 1 1 d R . . H3' H 0.8704 0.0248 -0.0425 0.029 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02068(12) 0.0286(2) 0.01747(16) -0.00456(16) -0.00228(8) 0.01429(10) N1 0.0206(10) 0.0351(11) 0.0166(9) 0.0040(8) 0.0002(8) 0.0147(9) C2 0.0303(13) 0.0512(16) 0.0224(11) 0.0158(12) 0.0054(11) 0.0215(11) C3 0.0237(11) 0.0270(11) 0.0197(11) 0.0045(9) 0.0000(9) 0.0116(9) C6 0.0232(10) 0.0242(11) 0.0146(11) 0.0029(8) 0.0017(8) 0.0123(9) C1 0.0241(13) 0.0559(17) 0.0276(13) 0.0137(11) 0.0103(10) 0.0203(13) C5 0.0192(10) 0.0333(12) 0.0228(12) 0.0057(9) 0.0018(9) 0.0142(9) O3 0.0214(7) 0.0260(9) 0.0316(8) -0.0106(8) -0.0028(6) 0.0071(8) O1 0.0279(9) 0.0436(10) 0.0254(9) 0.0173(9) 0.0044(8) 0.0193(7) O2 0.0280(9) 0.0486(10) 0.0355(10) 0.0218(7) 0.0073(7) 0.0225(8) C4 0.0250(11) 0.0252(11) 0.0218(12) 0.0037(9) -0.0042(9) 0.0129(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 2.0830(14) 4 ? Zn1 O3 2.0830(14) . ? Zn1 O1 2.1205(14) 2_655 ? Zn1 O1 2.1205(14) 5_654 ? Zn1 N1 2.1456(17) 4 ? Zn1 N1 2.1456(17) . ? N1 C6 1.337(2) . ? N1 C1 1.348(3) . ? C2 C3 1.381(3) . ? C2 C1 1.390(3) . ? C3 C5 1.382(3) . ? C3 C4 1.514(3) . ? C6 C5 1.387(3) . ? C6 C6 1.488(4) 4 ? O1 C4 1.251(3) . ? O1 Zn1 2.1205(14) 3_664 ? O2 C4 1.258(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O3 96.54(10) 4 . ? O3 Zn1 O1 91.74(5) 4 2_655 ? O3 Zn1 O1 89.41(8) . 2_655 ? O3 Zn1 O1 89.41(8) 4 5_654 ? O3 Zn1 O1 91.74(5) . 5_654 ? O1 Zn1 O1 178.27(11) 2_655 5_654 ? O3 Zn1 N1 93.14(6) 4 4 ? O3 Zn1 N1 169.86(8) . 4 ? O1 Zn1 N1 87.30(6) 2_655 4 ? O1 Zn1 N1 91.35(7) 5_654 4 ? O3 Zn1 N1 169.86(8) 4 . ? O3 Zn1 N1 93.14(6) . . ? O1 Zn1 N1 91.35(7) 2_655 . ? O1 Zn1 N1 87.30(6) 5_654 . ? N1 Zn1 N1 77.36(9) 4 . ? C6 N1 C1 118.45(19) . . ? C6 N1 Zn1 114.71(13) . . ? C1 N1 Zn1 126.55(15) . . ? C3 C2 C1 119.4(2) . . ? C2 C3 C5 118.04(19) . . ? C2 C3 C4 122.3(2) . . ? C5 C3 C4 119.65(19) . . ? N1 C6 C5 121.93(19) . . ? N1 C6 C6 116.45(11) . 4 ? C5 C6 C6 121.61(12) . 4 ? N1 C1 C2 122.2(2) . . ? C3 C5 C6 120.00(19) . . ? C4 O1 Zn1 127.79(14) . 3_664 ? O1 C4 O2 126.30(19) . . ? O1 C4 C3 116.59(19) . . ? O2 C4 C3 117.11(19) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.338 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.051 #==END #==END data_1P-3 _database_code_depnum_ccdc_archive 'CCDC 872242' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O6 Zn' _chemical_formula_sum 'C12 H10 N2 O6 Zn' _chemical_formula_weight 343.59 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 trigonal _symmetry_space_group_name_H-M P3(1)2(1) _symmetry_space_group_name_Hall P3(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 11.9109(6) _cell_length_b 11.9109(6) _cell_length_c 8.3215(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1022.40(13) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2847 _cell_measurement_theta_min 3.1454 _cell_measurement_theta_max 27.4740 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.831 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9310 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Mercury70 (2x2 bin mode) ; _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 14.6306 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6483 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1211 _reflns_number_gt 1179 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0251P)^2^+0.6594P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 1211 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.71212(4) 0.71212(4) 0.0000 0.02194(14) Uani 1 2 d S . . O1 O 0.7881(3) 0.87133(18) 0.1537(2) 0.0285(5) Uani 1 1 d . . . H3A H 0.7425 0.8690 0.2411 0.034 Uiso 1 1 d R . . H3B H 0.8652 0.9422 0.1331 0.034 Uiso 1 1 d R . . O2 O 0.1729(2) 0.3774(3) 0.5295(2) 0.0318(5) Uani 1 1 d . . . N1 N 0.5398(2) 0.6038(2) 0.1415(3) 0.0250(7) Uani 1 1 d . . . C4 C 0.4046(3) 0.5530(4) 0.3736(4) 0.0335(7) Uani 1 1 d . . . H4A H 0.3858 0.5809 0.4732 0.040 Uiso 1 1 d R . . C5 C 0.5147(3) 0.6350(3) 0.2855(4) 0.0376(9) Uani 1 1 d . . . H5A H 0.5800 0.7119 0.3378 0.045 Uiso 1 1 d R . . C3 C 0.3175(3) 0.4331(3) 0.3115(4) 0.0247(7) Uani 1 1 d . . . O3 O 0.1262(2) 0.2296(2) 0.3369(3) 0.0358(6) Uani 1 1 d . . . C6 C 0.1949(3) 0.3380(3) 0.4002(4) 0.0236(7) Uani 1 1 d . . . C2 C 0.3436(3) 0.4008(3) 0.1624(3) 0.0258(7) Uani 1 1 d . . . H2A H 0.2898 0.3149 0.1207 0.031 Uiso 1 1 d R . . C1 C 0.4549(3) 0.4868(3) 0.0797(3) 0.0209(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02105(19) 0.02105(19) 0.0185(2) 0.00221(11) -0.00221(11) 0.0066(2) O1 0.0310(14) 0.0224(10) 0.0300(11) -0.0001(8) -0.0030(13) 0.0117(12) O2 0.0332(12) 0.0275(13) 0.0268(12) -0.0027(12) 0.0134(10) 0.0092(12) N1 0.0262(13) 0.0211(16) 0.0177(12) -0.0016(11) 0.0028(10) 0.0044(12) C4 0.0376(17) 0.031(2) 0.0241(15) -0.0046(16) 0.0106(13) 0.0115(18) C5 0.0388(19) 0.0238(18) 0.0264(17) -0.0095(15) 0.0038(15) -0.0023(15) C3 0.0283(16) 0.0216(17) 0.0204(15) 0.0012(14) 0.0037(13) 0.0096(14) O3 0.0334(13) 0.0261(13) 0.0375(14) -0.0067(10) 0.0142(10) 0.0071(11) C6 0.0266(16) 0.0247(17) 0.0216(16) 0.0014(14) 0.0060(14) 0.0143(14) C2 0.0268(16) 0.0196(15) 0.0230(16) -0.0031(13) 0.0041(13) 0.0056(14) C1 0.0237(15) 0.0197(15) 0.0171(15) -0.0023(12) -0.0002(12) 0.0092(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 Zn1 O1 2.0820(19) . ? Zn1 O1 2.0820(19) 4 ? Zn1 O2 2.118(2) 2_664 ? Zn1 O2 2.118(2) 5_665 ? Zn1 N1 2.148(2) 4 ? Zn1 N1 2.148(2) . ? O2 C6 1.252(4) . ? O2 Zn1 2.118(2) 3_565 ? N1 C5 1.333(4) . ? N1 C1 1.349(4) . ? C4 C3 1.379(4) . ? C4 C5 1.389(4) . ? C3 C2 1.380(4) . ? C3 C6 1.519(4) . ? O3 C6 1.248(4) . ? C2 C1 1.387(4) . ? C1 C1 1.481(6) 4 ? 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 95.45(14) . 4 ? O1 Zn1 O2 89.71(12) . 2_664 ? O1 Zn1 O2 91.59(8) 4 2_664 ? O1 Zn1 O2 91.59(8) . 5_665 ? O1 Zn1 O2 89.71(12) 4 5_665 ? O2 Zn1 O2 178.06(17) 2_664 5_665 ? O1 Zn1 N1 170.65(12) . 4 ? O1 Zn1 N1 93.44(9) 4 4 ? O2 Zn1 N1 87.15(9) 2_664 4 ? O2 Zn1 N1 91.34(11) 5_665 4 ? O1 Zn1 N1 93.44(9) . . ? O1 Zn1 N1 170.65(12) 4 . ? O2 Zn1 N1 91.34(11) 2_664 . ? O2 Zn1 N1 87.15(9) 5_665 . ? N1 Zn1 N1 77.85(13) 4 . ? C6 O2 Zn1 127.4(2) . 3_565 ? C5 N1 C1 118.3(3) . . ? C5 N1 Zn1 127.3(2) . . ? C1 N1 Zn1 114.16(19) . . ? C3 C4 C5 119.2(3) . . ? N1 C5 C4 122.9(3) . . ? C4 C3 C2 117.9(3) . . ? C4 C3 C6 122.4(3) . . ? C2 C3 C6 119.7(3) . . ? O3 C6 O2 126.8(3) . . ? O3 C6 C3 117.0(3) . . ? O2 C6 C3 116.2(3) . . ? C3 C2 C1 120.4(3) . . ? N1 C1 C2 121.4(3) . . ? N1 C1 C1 116.77(16) . 4 ? C2 C1 C1 121.88(16) . 4 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.285 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.052