# Copyright The Royal Society of Chemistry, 1998 # Paper No. 8/00014J # Title: "New metal-binding for 5-aminoorotic acid : preparation, # characterization and crystal structures of zinc(II) complexes" # Authors: N.Lalioti, C.P.Raptopoulou, A.Terzis, A.Panagiotopoulos, # S.P.Perlepes and E.Manessi-Zoupa # Crystallographic data for compound 1 of the above manuscript data_1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[{Zn(C5 H3 N3 O4)(H2O)2}n]' _chemical_formula_analytical '[{Zn(5-amino-orotate)(H2O)2}n]' _chemical_formula_sum 'C5 H7 N3 O6 Zn' _chemical_formula_weight 270.51 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.530(1) _cell_length_b 7.124(1) _cell_length_c 10.425(1) _cell_angle_alpha 93.44(1) _cell_angle_beta 101.38(1) _cell_angle_gamma 94.58(1) _cell_volume 400.13(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.5 _cell_measurement_theta_max 11.5 _exptl_crystal_description 'parallelipiped' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 2.22 _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'floating method' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 3.09 _exptl_absorpt_correction_type 'psi-scan empirical' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Crystal Logic Dual Goniometer diffractometer' _diffrn_measurement_method 'theta-2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.3 _diffrn_reflns_number 1576 _diffrn_reflns_av_R_equivalents 0.0088 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1416 _reflns_number_observed 1331 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Program COLLECT (UCLA Crystallographic package)' _computing_cell_refinement 'Program LEAST (UCLA Crystallographic package)' _computing_data_reduction 'Program REDUCE (UCLA Crystallographic package)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0182P)^2^+0.5443P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'found in the difference Fourier map' _refine_ls_hydrogen_treatment 'isotropic refinement' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1414 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_obs 0.0251 _refine_ls_wR_factor_all 0.0747 _refine_ls_wR_factor_obs 0.0698 _refine_ls_goodness_of_fit_all 1.089 _refine_ls_goodness_of_fit_obs 1.099 _refine_ls_restrained_S_all 1.135 _refine_ls_restrained_S_obs 1.099 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn Zn 0.42977(6) 0.40351(4) 0.23290(3) 0.01951(14) Uani 1 d . . O1 O 0.6650(4) 0.2625(3) 0.1333(2) 0.0204(4) Uani 1 d . . O2 O 0.1310(5) 0.1913(3) 0.4377(2) 0.0344(6) Uani 1 d . . O3 O 0.7984(4) -0.0187(3) 0.1010(2) 0.0291(5) Uani 1 d . . O4 O 0.1990(4) -0.4217(3) 0.3180(2) 0.0245(5) Uani 1 d . . OW1 O 0.1279(5) 0.3341(3) 0.0585(2) 0.0249(5) Uani 1 d . . OW2 O 0.7297(7) 0.4800(5) 0.3945(3) 0.0327(7) Uani 1 d . . N1 N 0.3783(4) 0.1336(3) 0.2922(2) 0.0169(5) Uani 1 d . . N2 N 0.5156(6) -0.3365(3) 0.1555(3) 0.0190(5) Uani 1 d . . N3 N 0.1780(5) -0.1130(3) 0.3806(3) 0.0198(5) Uani 1 d . . C2 C 0.2263(6) 0.0785(4) 0.3718(3) 0.0199(6) Uani 1 d . . C4 C 0.2616(5) -0.2503(4) 0.3096(3) 0.0178(6) Uani 1 d . . C5 C 0.4273(5) -0.1868(4) 0.2280(3) 0.0157(5) Uani 1 d . . C6 C 0.4811(5) 0.0030(4) 0.2252(3) 0.0147(5) Uani 1 d . . C7 C 0.6639(5) 0.0865(4) 0.1458(3) 0.0164(6) Uani 1 d . . HAW1 H 0.1232(83) 0.2246(68) 0.0218(44) 0.046(12) Uiso 1 d . . HBW1 H 0.0139(92) 0.3315(63) 0.0793(44) 0.041(14) Uiso 1 d . . HAW2 H 0.7397(91) 0.5592(74) 0.4568(52) 0.055(14) Uiso 1 d . . HBW2 H 0.8110(79) 0.4650(66) 0.3862(46) 0.016(15) Uiso 1 d . . HAN2 H 0.4303(75) -0.3427(54) 0.0747(42) 0.035(10) Uiso 1 d . . HBN2 H 0.6485(80) -0.3124(53) 0.1602(36) 0.027(11) Uiso 1 d . . HN3 H 0.1069(66) -0.1396(50) 0.4239(35) 0.017(9) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0254(2) 0.0112(2) 0.0254(2) 0.00310(13) 0.01240(14) 0.00338(13) O1 0.0246(10) 0.0121(9) 0.0287(11) 0.0044(8) 0.0148(9) 0.0018(8) O2 0.054(2) 0.0131(10) 0.0500(14) 0.0030(10) 0.0420(13) 0.0055(10) O3 0.0313(12) 0.0190(11) 0.0449(13) 0.0014(9) 0.0261(11) 0.0048(9) O4 0.0341(12) 0.0106(10) 0.0360(12) 0.0049(8) 0.0238(10) 0.0021(8) OW1 0.0214(12) 0.0228(12) 0.0322(12) -0.0014(9) 0.0103(10) 0.0019(9) OW2 0.025(2) 0.040(2) 0.031(2) -0.0089(11) 0.0043(13) 0.0039(13) N1 0.0229(12) 0.0099(11) 0.0214(12) 0.0027(9) 0.0123(10) 0.0027(9) N2 0.0236(15) 0.0130(12) 0.0230(14) 0.0010(9) 0.0111(11) 0.0027(10) N3 0.0280(14) 0.0141(12) 0.0244(13) 0.0063(10) 0.0200(12) 0.0037(10) C2 0.0256(15) 0.0122(13) 0.0259(15) 0.0031(11) 0.0136(12) 0.0029(11) C4 0.0201(14) 0.0149(14) 0.0206(13) 0.0041(11) 0.0075(11) 0.0041(11) C5 0.0205(14) 0.0121(13) 0.0175(13) 0.0034(10) 0.0089(11) 0.0057(10) C6 0.0163(13) 0.0144(13) 0.0153(12) 0.0045(10) 0.0061(10) 0.0036(10) C7 0.0162(13) 0.0160(14) 0.0188(13) 0.0007(10) 0.0085(11) 0.0003(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn N1 2.070(2) . ? Zn O1 2.096(2) . ? Zn N2 2.121(2) 1_565 ? Zn OW2 2.128(3) . ? Zn O4 2.129(2) 1_565 ? Zn OW1 2.213(2) . ? O1 C7 1.268(3) . ? O2 C2 1.240(4) . ? O3 C7 1.232(3) . ? O4 C4 1.256(3) . ? O4 Zn 2.129(2) 1_545 ? N1 C2 1.346(4) . ? N1 C6 1.357(4) . ? N2 C5 1.442(4) . ? N2 Zn 2.121(2) 1_545 ? N3 C4 1.356(4) . ? N3 C2 1.381(4) . ? C4 C5 1.433(4) . ? C5 C6 1.365(4) . ? C6 C7 1.534(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 N1 Zn O1 79.42(8) . . ? N1 Zn N2 171.85(9) . 1_565 ? O1 Zn N2 92.44(9) . 1_565 ? N1 Zn OW2 91.87(11) . . ? O1 Zn OW2 90.25(12) . . ? N2 Zn OW2 88.53(12) 1_565 . ? N1 Zn O4 108.35(8) . 1_565 ? O1 Zn O4 172.10(7) . 1_565 ? N2 Zn O4 79.78(9) 1_565 1_565 ? OW2 Zn O4 90.92(12) . 1_565 ? N1 Zn OW1 90.71(9) . . ? O1 Zn OW1 88.60(9) . . ? N2 Zn OW1 88.68(10) 1_565 . ? OW2 Zn OW1 176.94(11) . . ? O4 Zn OW1 89.83(9) 1_565 . ? C7 O1 Zn 115.4(2) . . ? C4 O4 Zn 110.8(2) . 1_545 ? C2 N1 C6 120.1(2) . . ? C2 N1 Zn 125.8(2) . . ? C6 N1 Zn 113.2(2) . . ? C5 N2 Zn 108.8(2) . 1_545 ? C4 N3 C2 124.8(3) . . ? O2 C2 N1 123.1(2) . . ? O2 C2 N3 119.2(3) . . ? N1 C2 N3 117.7(2) . . ? O4 C4 N3 121.1(3) . . ? O4 C4 C5 123.0(3) . . ? N3 C4 C5 115.9(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 N2 127.4(3) . . ? C4 C5 N2 114.4(2) . . ? N1 C6 C5 123.0(3) . . ? N1 C6 C7 114.4(2) . . ? C5 C6 C7 122.6(2) . . ? O3 C7 O1 125.1(3) . . ? O3 C7 C6 118.9(2) . . ? O1 C7 C6 116.0(2) . . ? _refine_diff_density_max 0.504 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.080 #===END # Crystallographic data for compound 3 of the above manuscript data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[Zn(C5 H4 N3 O4)2(H2 O)2(C2 H6 O S)2]' _chemical_formula_analytical '[Zn(5-amino-orotate)2(H2O)2(DMSO)2]' _chemical_formula_sum 'C14 H24 N6 O12 S2 Zn' _chemical_formula_weight 597.9 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.249(1) _cell_length_b 9.074(2) _cell_length_c 11.826(3) _cell_angle_alpha 98.90(1) _cell_angle_beta 91.25(1) _cell_angle_gamma 100.77(1) _cell_volume 545.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 27 _exptl_crystal_description 'parallelipiped' _exptl_crystal_colour 'bright yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.79 _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'floating method' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 4.065 _exptl_absorpt_correction_type 'psi-scan empirical' _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'P21 Nicolet' _diffrn_measurement_method 'theta-2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -2.7 _diffrn_reflns_number 1951 _diffrn_reflns_av_R_equivalents 0.0080 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 64.99 _reflns_number_total 1851 _reflns_number_observed 1776 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Program COLLECT (UCLA Crystallographic package)' _computing_cell_refinement 'Program LEAST (UCLA Crystallographic package)' _computing_data_reduction 'Program REDUCE (UCLA Crystallographic package)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.4254P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'found in difference Fourier map' _refine_ls_hydrogen_treatment 'isotropic refinement' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1851 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_obs 0.0386 _refine_ls_wR_factor_all 0.1073 _refine_ls_wR_factor_obs 0.1058 _refine_ls_goodness_of_fit_all 1.086 _refine_ls_goodness_of_fit_obs 1.096 _refine_ls_restrained_S_all 1.086 _refine_ls_restrained_S_obs 1.096 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn Zn 0.5000 0.0000 0.5000 0.0182(2) Uani 1 d S . OW1 O 0.2917(4) 0.1752(2) 0.4848(2) 0.0237(4) Uani 1 d . . O1 O 0.2402(3) -0.0743(2) 0.62127(15) 0.0241(4) Uani 1 d . . O5 O 0.7675(3) 0.1318(2) 0.63092(15) 0.0254(4) Uani 1 d . . N1 N -0.0619(4) -0.0505(2) 0.7973(2) 0.0196(4) Uani 1 d . . C2 C -0.2349(5) -0.0316(3) 0.8780(2) 0.0199(5) Uani 1 d . . O2 O -0.3576(4) 0.0725(2) 0.8876(2) 0.0290(4) Uani 1 d . . N3 N -0.2661(4) -0.1375(2) 0.9510(2) 0.0220(5) Uani 1 d . . C4 C -0.1462(5) -0.2599(3) 0.9464(2) 0.0228(5) Uani 1 d . . O4 O -0.1977(4) -0.3531(2) 1.0103(2) 0.0375(5) Uani 1 d . . C5 C 0.0484(5) -0.2702(3) 0.8587(2) 0.0194(5) Uani 1 d . . N2 N 0.1714(5) -0.3902(3) 0.8560(2) 0.0305(5) Uani 1 d . . C6 C 0.0799(5) -0.1671(3) 0.7850(2) 0.0182(5) Uani 1 d . . C7 C 0.2600(4) -0.1675(3) 0.6899(2) 0.0186(5) Uani 1 d . . O3 O 0.4140(4) -0.2584(2) 0.6826(2) 0.0266(4) Uani 1 d . . S S 0.81020(13) 0.28676(7) 0.70578(6) 0.0262(2) Uani 1 d . . C8 C 0.5021(8) 0.3178(5) 0.7529(3) 0.0458(8) Uani 1 d . . C9 C 0.8575(8) 0.4203(4) 0.6078(3) 0.0425(8) Uani 1 d . . HW1A H 0.3728(114) 0.2178(68) 0.4165(52) 0.102(19) Uiso 1 d . . HW1B H 0.1589(94) 0.1499(54) 0.4721(40) 0.061(15) Uiso 1 d . . HN1 H -0.0666(64) 0.0008(40) 0.7482(32) 0.031(9) Uiso 1 d . . HN2A H 0.3143(70) -0.3915(40) 0.8070(32) 0.036(9) Uiso 1 d . . HN2B H 0.1579(79) -0.4366(46) 0.9062(38) 0.048(11) Uiso 1 d . . HN3 H -0.3819(78) -0.1317(44) 1.0031(35) 0.040(10) Uiso 1 d . . H8A H 0.4005(100) 0.3298(55) 0.6929(46) 0.078(15) Uiso 1 d . . H8B H 0.5438(103) 0.4101(64) 0.8003(49) 0.086(17) Uiso 1 d . . H8C H 0.4308(126) 0.2230(76) 0.7746(55) 0.118(22) Uiso 1 d . . H9A H 0.7141(86) 0.4006(47) 0.5571(38) 0.058(12) Uiso 1 d . . H9B H 0.8384(88) 0.5159(55) 0.6527(41) 0.067(13) Uiso 1 d . . H9C H 1.0121(107) 0.4199(55) 0.5783(43) 0.075(15) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0180(3) 0.0194(3) 0.0193(3) 0.0060(2) 0.0051(2) 0.0062(2) OW1 0.0203(10) 0.0249(9) 0.0284(10) 0.0087(7) 0.0055(8) 0.0068(8) O1 0.0231(9) 0.0307(10) 0.0237(9) 0.0124(7) 0.0079(7) 0.0105(7) O5 0.0284(9) 0.0220(9) 0.0261(9) 0.0007(7) 0.0004(7) 0.0084(7) N1 0.0236(11) 0.0209(10) 0.0181(10) 0.0087(9) 0.0066(8) 0.0086(8) C2 0.0207(12) 0.0228(12) 0.0169(12) 0.0026(9) 0.0035(9) 0.0062(10) O2 0.0359(10) 0.0291(10) 0.0295(10) 0.0110(8) 0.0147(8) 0.0189(8) N3 0.0240(11) 0.0253(11) 0.0199(11) 0.0074(8) 0.0094(9) 0.0090(8) C4 0.0254(13) 0.0238(12) 0.0202(12) 0.0064(10) 0.0051(10) 0.0047(10) O4 0.0481(12) 0.0359(11) 0.0393(12) 0.0234(9) 0.0224(9) 0.0186(9) C5 0.0214(12) 0.0197(12) 0.0186(12) 0.0037(9) 0.0032(9) 0.0070(9) N2 0.0395(14) 0.0282(12) 0.0331(13) 0.0170(11) 0.0147(11) 0.0189(10) C6 0.0182(11) 0.0189(11) 0.0184(11) 0.0036(9) 0.0028(9) 0.0052(9) C7 0.0181(12) 0.0191(11) 0.0184(12) 0.0034(9) 0.0010(9) 0.0028(9) O3 0.0270(9) 0.0288(10) 0.0302(10) 0.0115(8) 0.0105(8) 0.0145(8) S 0.0335(4) 0.0222(4) 0.0232(4) 0.0020(3) -0.0013(3) 0.0077(3) C8 0.057(2) 0.054(2) 0.037(2) 0.010(2) 0.017(2) 0.037(2) C9 0.056(2) 0.032(2) 0.040(2) 0.0135(14) -0.001(2) 0.0009(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 Zn O1 2.100(2) . ? Zn O1 2.100(2) 2_656 ? Zn OW1 2.117(2) 2_656 ? Zn OW1 2.117(2) . ? Zn O5 2.122(2) . ? Zn O5 2.122(2) 2_656 ? O1 C7 1.275(3) . ? O5 S 1.517(2) . ? N1 C2 1.346(3) . ? N1 C6 1.395(3) . ? C2 O2 1.232(3) . ? C2 N3 1.378(3) . ? N3 C4 1.371(4) . ? C4 O4 1.217(3) . ? C4 C5 1.477(3) . ? C5 N2 1.363(3) . ? C5 C6 1.364(4) . ? C6 C7 1.485(3) . ? C7 O3 1.253(3) . ? S C8 1.779(3) . ? S C9 1.791(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 O1 Zn O1 180.0 . 2_656 ? O1 Zn OW1 91.11(7) . 2_656 ? O1 Zn OW1 88.89(7) 2_656 2_656 ? O1 Zn OW1 88.89(7) . . ? O1 Zn OW1 91.11(7) 2_656 . ? OW1 Zn OW1 180.0 2_656 . ? O1 Zn O5 91.54(7) . . ? O1 Zn O5 88.46(7) 2_656 . ? OW1 Zn O5 85.02(7) 2_656 . ? OW1 Zn O5 94.98(7) . . ? O1 Zn O5 88.46(7) . 2_656 ? O1 Zn O5 91.54(7) 2_656 2_656 ? OW1 Zn O5 94.98(7) 2_656 2_656 ? OW1 Zn O5 85.02(7) . 2_656 ? O5 Zn O5 180.0 . 2_656 ? C7 O1 Zn 128.9(2) . . ? S O5 Zn 138.56(11) . . ? C2 N1 C6 124.3(2) . . ? O2 C2 N1 123.3(2) . . ? O2 C2 N3 121.5(2) . . ? N1 C2 N3 115.2(2) . . ? C4 N3 C2 126.6(2) . . ? O4 C4 N3 122.0(2) . . ? O4 C4 C5 122.8(2) . . ? N3 C4 C5 115.2(2) . . ? N2 C5 C6 126.0(2) . . ? N2 C5 C4 115.1(2) . . ? C6 C5 C4 118.8(2) . . ? C5 C6 N1 119.7(2) . . ? C5 C6 C7 124.7(2) . . ? N1 C6 C7 115.6(2) . . ? O3 C7 O1 125.7(2) . . ? O3 C7 C6 118.5(2) . . ? O1 C7 C6 115.8(2) . . ? O5 S C8 107.4(2) . . ? O5 S C9 105.06(14) . . ? C8 S C9 98.1(2) . . ? _refine_diff_density_max 0.635 _refine_diff_density_min -0.994 _refine_diff_density_rms 0.090 #===END