# Electronic Supplementary MAterial for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yue-Peng Cai' _publ_contact_author_email YPCAI8@YAHOO.COM _publ_section_title ; Temperature- and solvent-controlled dimensionality in a zinc 6-(1H-benzoimidazol-2-yl)pyridinecarboxylate system ; loop_ _publ_author_name 'Yue-Peng Cai' 'Li Chen' 'Hua-Cai Fang' 'Xiao-Ming Lin' 'An-Wu Xu' ; Zheng-Yuan Zhou ; # Attachment '707898.cif' data_c1 _database_code_depnum_ccdc_archive 'CCDC 707898' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 N6 O4 Zn, 2(H2 O)' _chemical_formula_sum 'C26 H20 N6 O6 Zn' _chemical_formula_weight 577.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8996(2) _cell_length_b 20.2275(3) _cell_length_c 13.4810(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.2470(10) _cell_angle_gamma 90.00 _cell_volume 2532.69(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4573 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 23.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7766 _exptl_absorpt_correction_T_max 0.8371 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18882 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4712 _reflns_number_gt 3740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0724P)^2^+2.5253P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4712 _refine_ls_number_parameters 379 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.002 _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 0.73294(2) 1.010063(10) 0.758121(14) 0.04080(6) Uani 1 1 d . . . O1 O 0.63781(13) 0.98019(6) 0.88404(9) 0.0490(4) Uani 1 1 d . . . O2 O 0.53326(17) 0.89021(9) 0.92052(11) 0.0840(5) Uani 1 1 d . . . O3 O 0.58994(13) 1.09238(6) 0.71839(9) 0.0492(4) Uani 1 1 d . . . O4 O 0.59671(17) 1.20221(7) 0.72666(15) 0.0817(6) Uani 1 1 d . . . O1W O 0.6019(2) 0.92733(12) 0.12869(15) 0.1205(8) Uani 1 1 d D . . H1WA H 0.5945(15) 0.9366(7) 0.0660(4) 0.181 Uiso 1 1 d D . . H1WB H 0.5555(9) 0.8930(4) 0.1334(11) 0.181 Uiso 1 1 d D . . O2W O 0.2761(4) 0.1726(2) 0.7262(4) 0.178(3) Uani 0.50 1 d PD . . H2WA H 0.2246(9) 0.1388(4) 0.7162(15) 0.267 Uiso 0.50 1 d PD . . H2WB H 0.3132(8) 0.1813(9) 0.6805(6) 0.267 Uiso 0.50 1 d PD . . O2W' O 0.3514(4) 0.2489(2) 0.5683(3) 0.251(3) Uani 0.50 1 d PD . . H2WA' H 0.3286(13) 0.2127(4) 0.5885(10) 0.377 Uiso 0.50 1 d PD . . H2WB' H 0.3859(8) 0.2484(11) 0.5196(5) 0.377 Uiso 0.50 1 d PD . . N1 N 0.75031(16) 1.00778(7) 0.59912(10) 0.0428(4) Uani 1 1 d . . . N2 N 0.66462(18) 0.95780(8) 0.44293(11) 0.0525(5) Uani 1 1 d . . . H2 H 0.6164 0.9305 0.3947 0.063 Uiso 1 1 calc R . . N3 N 0.60386(14) 0.93593(7) 0.69175(10) 0.0393(4) Uani 1 1 d . . . N4 N 0.92488(13) 0.95711(7) 0.83694(9) 0.0360(4) Uani 1 1 d . . . N5 N 1.15808(14) 0.96703(7) 0.92996(10) 0.0401(4) Uani 1 1 d . . . H5 H 1.2394 0.9851 0.9646 0.048 Uiso 1 1 calc R . . N6 N 0.86228(14) 1.08201(7) 0.82691(9) 0.0356(4) Uani 1 1 d . . . C1 C 0.80832(19) 1.03854(9) 0.53189(13) 0.0458(5) Uani 1 1 d . . . C2 C 0.9052(2) 1.09030(11) 0.54955(16) 0.0603(6) Uani 1 1 d . . . H2A H 0.9417 1.1108 0.6152 0.072 Uiso 1 1 calc R . . C3 C 0.9454(2) 1.11042(13) 0.46597(18) 0.0751(8) Uani 1 1 d . . . H3 H 1.0106 1.1450 0.4751 0.090 Uiso 1 1 calc R . . C4 C 0.8890(3) 1.07916(14) 0.36758(17) 0.0814(8) Uani 1 1 d . . . H4 H 0.9173 1.0942 0.3126 0.098 Uiso 1 1 calc R . . C5 C 0.7947(3) 1.02768(13) 0.34848(15) 0.0705(7) Uani 1 1 d . . . H5A H 0.7589 1.0076 0.2825 0.085 Uiso 1 1 calc R . . C6 C 0.7545(2) 1.00673(10) 0.43244(14) 0.0509(6) Uani 1 1 d . . . C7 C 0.66608(19) 0.96050(9) 0.54349(12) 0.0441(5) Uani 1 1 d . . . C8 C 0.58829(19) 0.91746(9) 0.59275(13) 0.0449(5) Uani 1 1 d . . . C9 C 0.5084(3) 0.86225(11) 0.54754(16) 0.0682(7) Uani 1 1 d . . . H9 H 0.4972 0.8497 0.4788 0.082 Uiso 1 1 calc R . . C10 C 0.4451(3) 0.82588(11) 0.60766(18) 0.0795(8) Uani 1 1 d . . . H10 H 0.3914 0.7883 0.5792 0.095 Uiso 1 1 calc R . . C11 C 0.4616(2) 0.84528(10) 0.70869(16) 0.0655(7) Uani 1 1 d . . . H11 H 0.4193 0.8214 0.7492 0.079 Uiso 1 1 calc R . . C12 C 0.54261(19) 0.90116(9) 0.74887(14) 0.0468(5) Uani 1 1 d . . . C13 C 0.57190(19) 0.92583(10) 0.86034(14) 0.0503(6) Uani 1 1 d . . . C14 C 0.98484(16) 0.89491(8) 0.85112(11) 0.0356(4) Uani 1 1 d . . . C15 C 0.9231(2) 0.83314(9) 0.81714(13) 0.0472(5) Uani 1 1 d . . . H15 H 0.8252 0.8289 0.7792 0.057 Uiso 1 1 calc R . . C16 C 1.0118(2) 0.77918(10) 0.84166(14) 0.0552(6) Uani 1 1 d . . . H16 H 0.9728 0.7375 0.8208 0.066 Uiso 1 1 calc R . . C17 C 1.1597(2) 0.78501(10) 0.89732(15) 0.0598(6) Uani 1 1 d . . . H17 H 1.2169 0.7473 0.9102 0.072 Uiso 1 1 calc R . . C18 C 1.2229(2) 0.84543(10) 0.93373(14) 0.0512(6) Uani 1 1 d . . . H18 H 1.3207 0.8492 0.9722 0.061 Uiso 1 1 calc R . . C19 C 1.13274(17) 0.90027(9) 0.90988(12) 0.0388(5) Uani 1 1 d . . . C20 C 1.03104(17) 0.99848(8) 0.88485(11) 0.0352(4) Uani 1 1 d . . . C21 C 1.00154(16) 1.06928(8) 0.88128(11) 0.0360(4) Uani 1 1 d . . . C22 C 1.09613(19) 1.12057(10) 0.92541(13) 0.0485(5) Uani 1 1 d . . . H22 H 1.1927 1.1122 0.9630 0.058 Uiso 1 1 calc R . . C23 C 1.0435(2) 1.18460(10) 0.91226(14) 0.0534(6) Uani 1 1 d . . . H23 H 1.1048 1.2197 0.9418 0.064 Uiso 1 1 calc R . . C24 C 0.9009(2) 1.19638(9) 0.85575(14) 0.0495(5) Uani 1 1 d . . . H24 H 0.8653 1.2394 0.8463 0.059 Uiso 1 1 calc R . . C25 C 0.81057(18) 1.14347(8) 0.81303(12) 0.0404(5) Uani 1 1 d . . . C26 C 0.6515(2) 1.14772(9) 0.74790(14) 0.0465(5) 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 0.04066(10) 0.03650(10) 0.04226(9) -0.00088(8) 0.01057(8) -0.00062(8) O1 0.0441(6) 0.0500(7) 0.0533(6) -0.0055(5) 0.0173(5) -0.0116(6) O2 0.0947(9) 0.0980(11) 0.0653(7) -0.0008(8) 0.0353(7) -0.0469(8) O3 0.0457(6) 0.0407(6) 0.0531(6) -0.0073(5) 0.0070(5) -0.0013(5) O4 0.0670(9) 0.0386(7) 0.1158(12) -0.0024(8) 0.0015(9) 0.0153(7) O1W 0.0930(11) 0.160(2) 0.1119(12) -0.0357(13) 0.0400(10) 0.0202(13) O2W 0.100(3) 0.152(4) 0.274(6) 0.115(4) 0.054(3) 0.053(3) O2W' 0.163(3) 0.199(4) 0.255(5) -0.132(4) -0.103(4) 0.132(3) N1 0.0529(8) 0.0384(8) 0.0327(6) -0.0014(6) 0.0091(6) -0.0017(6) N2 0.0702(9) 0.0453(8) 0.0343(6) -0.0070(6) 0.0083(6) 0.0015(8) N3 0.0372(6) 0.0336(7) 0.0397(6) 0.0032(6) 0.0041(5) -0.0012(6) N4 0.0312(6) 0.0410(7) 0.0335(6) 0.0000(5) 0.0080(5) -0.0018(6) N5 0.0290(6) 0.0423(7) 0.0445(6) 0.0006(6) 0.0071(5) -0.0051(6) N6 0.0390(6) 0.0352(7) 0.0320(5) -0.0010(5) 0.0115(5) -0.0011(6) C1 0.0499(9) 0.0448(10) 0.0407(7) 0.0054(7) 0.0131(7) 0.0058(8) C2 0.0632(11) 0.0569(12) 0.0572(10) 0.0045(9) 0.0161(9) -0.0053(10) C3 0.0690(12) 0.0764(15) 0.0857(12) 0.0232(11) 0.0343(10) -0.0030(12) C4 0.0848(13) 0.1085(19) 0.0666(10) 0.0246(12) 0.0460(9) 0.0140(14) C5 0.0893(14) 0.0805(15) 0.0479(9) 0.0036(10) 0.0315(9) 0.0111(13) C6 0.0563(10) 0.0557(11) 0.0392(8) 0.0022(8) 0.0147(7) 0.0120(9) C7 0.0518(9) 0.0383(9) 0.0349(7) -0.0012(7) 0.0058(7) 0.0064(8) C8 0.0489(9) 0.0353(9) 0.0395(8) 0.0018(7) 0.0012(7) -0.0014(8) C9 0.0889(15) 0.0500(11) 0.0461(10) -0.0070(9) -0.0015(10) -0.0158(11) C10 0.0963(16) 0.0506(11) 0.0650(12) -0.0014(10) -0.0058(12) -0.0327(11) C11 0.0686(12) 0.0534(11) 0.0580(11) 0.0107(9) 0.0010(10) -0.0225(10) C12 0.0390(8) 0.0415(9) 0.0494(9) 0.0073(8) 0.0019(7) -0.0075(8) C13 0.0391(8) 0.0561(11) 0.0532(9) 0.0031(8) 0.0129(7) -0.0094(8) C14 0.0340(7) 0.0396(9) 0.0331(6) -0.0023(6) 0.0116(6) -0.0018(7) C15 0.0450(9) 0.0486(10) 0.0443(8) -0.0066(8) 0.0108(7) -0.0052(8) C16 0.0644(11) 0.0389(10) 0.0581(10) -0.0101(8) 0.0159(9) -0.0012(9) C17 0.0669(11) 0.0481(11) 0.0632(10) 0.0004(9) 0.0211(9) 0.0152(10) C18 0.0411(9) 0.0534(11) 0.0555(9) 0.0026(8) 0.0119(8) 0.0081(8) C19 0.0360(7) 0.0423(9) 0.0379(7) -0.0003(7) 0.0126(6) 0.0003(7) C20 0.0328(7) 0.0418(9) 0.0307(6) 0.0007(6) 0.0106(6) -0.0035(7) C21 0.0366(7) 0.0388(9) 0.0336(6) 0.0000(6) 0.0134(6) -0.0040(7) C22 0.0423(9) 0.0527(11) 0.0467(8) -0.0006(8) 0.0106(7) -0.0090(8) C23 0.0561(10) 0.0435(10) 0.0551(9) -0.0077(8) 0.0122(8) -0.0174(9) C24 0.0594(10) 0.0330(9) 0.0549(9) -0.0037(8) 0.0186(8) -0.0063(8) C25 0.0494(9) 0.0352(8) 0.0361(7) -0.0014(6) 0.0143(6) 0.0001(7) C26 0.0484(9) 0.0386(9) 0.0482(8) -0.0055(7) 0.0115(7) 0.0043(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N6 1.9481(13) . ? Zn1 N3 1.9725(13) . ? Zn1 N4 2.1188(12) . ? Zn1 O3 2.1304(12) . ? Zn1 N1 2.2093(15) . ? Zn1 O1 2.2891(14) . ? O1 C13 1.262(2) . ? O2 C13 1.240(3) . ? O3 C26 1.271(2) . ? O4 C26 1.218(2) . ? O1W H1WA 0.843(6) . ? O1W H1WB 0.846(7) . ? O2W H2WA 0.836(7) . ? O2W H2WB 0.837(8) . ? O2W' H2WB' 0.838(7) . ? O2W' H2WA' 0.839(7) . ? N1 C7 1.319(2) . ? N1 C1 1.378(3) . ? N2 C7 1.352(2) . ? N2 C6 1.371(3) . ? N2 H2 0.8600 . ? N3 C12 1.334(3) . ? N3 C8 1.342(2) . ? N4 C20 1.324(2) . ? N4 C14 1.376(2) . ? N5 C20 1.352(2) . ? N5 C19 1.383(2) . ? N5 H5 0.8600 . ? N6 C25 1.333(2) . ? N6 C21 1.3433(19) . ? C1 C2 1.383(3) . ? C1 C6 1.415(2) . ? C2 C3 1.380(4) . ? C2 H2A 0.9300 . ? C3 C4 1.399(3) . ? C3 H3 0.9300 . ? C4 C5 1.363(4) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5A 0.9300 . ? C7 C8 1.465(3) . ? C8 C9 1.382(3) . ? C9 C10 1.394(4) . ? C9 H9 0.9300 . ? C10 C11 1.372(3) . ? C10 H10 0.9300 . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.513(3) . ? C14 C15 1.397(2) . ? C14 C19 1.407(2) . ? C15 C16 1.368(3) . ? C15 H15 0.9300 . ? C16 C17 1.400(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C20 C21 1.459(2) . ? C21 C22 1.386(2) . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.373(3) . ? C23 H23 0.9300 . ? C24 C25 1.386(2) . ? C24 H24 0.9300 . ? C25 C26 1.517(2) . ? 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 N6 Zn1 N3 178.57(5) . . ? N6 Zn1 N4 79.12(5) . . ? N3 Zn1 N4 99.84(5) . . ? N6 Zn1 O3 78.81(5) . . ? N3 Zn1 O3 102.14(5) . . ? N4 Zn1 O3 157.48(5) . . ? N6 Zn1 N1 102.62(6) . . ? N3 Zn1 N1 78.45(6) . . ? N4 Zn1 N1 96.81(5) . . ? O3 Zn1 N1 92.32(5) . . ? N6 Zn1 O1 102.44(5) . . ? N3 Zn1 O1 76.55(5) . . ? N4 Zn1 O1 91.28(5) . . ? O3 Zn1 O1 89.12(5) . . ? N1 Zn1 O1 154.69(5) . . ? C13 O1 Zn1 110.59(12) . . ? C26 O3 Zn1 113.89(11) . . ? H1WA O1W H1WB 113.3(12) . . ? H2WA O2W H2WB 116.8(17) . . ? H2WB' O2W' H2WA' 118.2(16) . . ? C7 N1 C1 106.19(14) . . ? C7 N1 Zn1 108.71(12) . . ? C1 N1 Zn1 144.96(11) . . ? C7 N2 C6 106.99(15) . . ? C7 N2 H2 126.5 . . ? C6 N2 H2 126.5 . . ? C12 N3 C8 120.57(15) . . ? C12 N3 Zn1 119.45(11) . . ? C8 N3 Zn1 119.73(12) . . ? C20 N4 C14 106.18(12) . . ? C20 N4 Zn1 110.36(11) . . ? C14 N4 Zn1 143.20(10) . . ? C20 N5 C19 107.10(13) . . ? C20 N5 H5 126.5 . . ? C19 N5 H5 126.5 . . ? C25 N6 C21 121.81(14) . . ? C25 N6 Zn1 118.21(10) . . ? C21 N6 Zn1 119.86(11) . . ? N1 C1 C2 130.57(17) . . ? N1 C1 C6 108.19(16) . . ? C2 C1 C6 121.23(19) . . ? C3 C2 C1 117.48(19) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 123.2(2) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C4 C5 C6 116.7(2) . . ? C4 C5 H5A 121.6 . . ? C6 C5 H5A 121.6 . . ? N2 C6 C5 133.10(18) . . ? N2 C6 C1 105.99(17) . . ? C5 C6 C1 120.90(19) . . ? N1 C7 N2 112.63(17) . . ? N1 C7 C8 120.08(15) . . ? N2 C7 C8 127.29(15) . . ? N3 C8 C9 120.97(19) . . ? N3 C8 C7 112.82(15) . . ? C9 C8 C7 126.19(18) . . ? C8 C9 C10 118.3(2) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 118.4(2) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? N3 C12 C11 121.52(18) . . ? N3 C12 C13 115.48(15) . . ? C11 C12 C13 122.97(19) . . ? O2 C13 O1 126.16(18) . . ? O2 C13 C12 117.48(17) . . ? O1 C13 C12 116.32(17) . . ? N4 C14 C15 130.83(14) . . ? N4 C14 C19 108.82(14) . . ? C15 C14 C19 120.35(15) . . ? C16 C15 C14 117.59(16) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? C15 C16 C17 121.81(18) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 121.70(19) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 116.58(16) . . ? C17 C18 H18 121.7 . . ? C19 C18 H18 121.7 . . ? N5 C19 C18 132.49(15) . . ? N5 C19 C14 105.55(14) . . ? C18 C19 C14 121.92(16) . . ? N4 C20 N5 112.34(14) . . ? N4 C20 C21 119.23(13) . . ? N5 C20 C21 128.41(14) . . ? N6 C21 C22 120.26(15) . . ? N6 C21 C20 111.23(13) . . ? C22 C21 C20 128.51(14) . . ? C23 C22 C21 118.47(16) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C24 C23 C22 120.18(17) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.22(17) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? N6 C25 C24 120.06(15) . . ? N6 C25 C26 113.92(14) . . ? C24 C25 C26 126.02(16) . . ? O4 C26 O3 126.69(17) . . ? O4 C26 C25 118.40(16) . . ? O3 C26 C25 114.87(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 Zn1 O1 C13 -167.56(11) . . . . ? N3 Zn1 O1 C13 11.40(11) . . . . ? N4 Zn1 O1 C13 -88.42(11) . . . . ? O3 Zn1 O1 C13 114.10(11) . . . . ? N1 Zn1 O1 C13 20.54(18) . . . . ? N6 Zn1 O3 C26 5.12(13) . . . . ? N3 Zn1 O3 C26 -175.97(13) . . . . ? N4 Zn1 O3 C26 16.8(2) . . . . ? N1 Zn1 O3 C26 -97.29(13) . . . . ? O1 Zn1 O3 C26 107.99(13) . . . . ? N6 Zn1 N1 C7 -179.80(11) . . . . ? N3 Zn1 N1 C7 1.17(12) . . . . ? N4 Zn1 N1 C7 99.88(12) . . . . ? O3 Zn1 N1 C7 -100.75(12) . . . . ? O1 Zn1 N1 C7 -7.90(19) . . . . ? N6 Zn1 N1 C1 -5.2(2) . . . . ? N3 Zn1 N1 C1 175.8(2) . . . . ? N4 Zn1 N1 C1 -85.5(2) . . . . ? O3 Zn1 N1 C1 73.9(2) . . . . ? O1 Zn1 N1 C1 166.71(17) . . . . ? N6 Zn1 N3 C12 38(3) . . . . ? N4 Zn1 N3 C12 81.14(13) . . . . ? O3 Zn1 N3 C12 -93.94(13) . . . . ? N1 Zn1 N3 C12 176.16(14) . . . . ? O1 Zn1 N3 C12 -7.82(12) . . . . ? N6 Zn1 N3 C8 -137(3) . . . . ? N4 Zn1 N3 C8 -93.20(13) . . . . ? O3 Zn1 N3 C8 91.72(13) . . . . ? N1 Zn1 N3 C8 1.82(12) . . . . ? O1 Zn1 N3 C8 177.84(13) . . . . ? N6 Zn1 N4 C20 -3.57(11) . . . . ? N3 Zn1 N4 C20 177.43(11) . . . . ? O3 Zn1 N4 C20 -15.2(2) . . . . ? N1 Zn1 N4 C20 98.03(12) . . . . ? O1 Zn1 N4 C20 -105.99(11) . . . . ? N6 Zn1 N4 C14 -176.6(2) . . . . ? N3 Zn1 N4 C14 4.4(2) . . . . ? O3 Zn1 N4 C14 171.77(17) . . . . ? N1 Zn1 N4 C14 -75.0(2) . . . . ? O1 Zn1 N4 C14 80.98(19) . . . . ? N3 Zn1 N6 C25 -136(3) . . . . ? N4 Zn1 N6 C25 -179.70(14) . . . . ? O3 Zn1 N6 C25 -4.22(13) . . . . ? N1 Zn1 N6 C25 85.66(13) . . . . ? O1 Zn1 N6 C25 -90.80(13) . . . . ? N3 Zn1 N6 C21 48(3) . . . . ? N4 Zn1 N6 C21 4.17(12) . . . . ? O3 Zn1 N6 C21 179.65(13) . . . . ? N1 Zn1 N6 C21 -90.46(13) . . . . ? O1 Zn1 N6 C21 93.07(13) . . . . ? C7 N1 C1 C2 -178.7(2) . . . . ? Zn1 N1 C1 C2 6.6(4) . . . . ? C7 N1 C1 C6 -0.3(2) . . . . ? Zn1 N1 C1 C6 -174.97(16) . . . . ? N1 C1 C2 C3 179.3(2) . . . . ? C6 C1 C2 C3 1.0(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C7 N2 C6 C5 -179.5(2) . . . . ? C7 N2 C6 C1 -0.3(2) . . . . ? C4 C5 C6 N2 -179.9(2) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? N1 C1 C6 N2 0.4(2) . . . . ? C2 C1 C6 N2 178.98(18) . . . . ? N1 C1 C6 C5 179.73(19) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? C1 N1 C7 N2 0.1(2) . . . . ? Zn1 N1 C7 N2 176.89(12) . . . . ? C1 N1 C7 C8 179.36(16) . . . . ? Zn1 N1 C7 C8 -3.9(2) . . . . ? C6 N2 C7 N1 0.1(2) . . . . ? C6 N2 C7 C8 -179.07(18) . . . . ? C12 N3 C8 C9 0.1(3) . . . . ? Zn1 N3 C8 C9 174.42(15) . . . . ? C12 N3 C8 C7 -178.50(15) . . . . ? Zn1 N3 C8 C7 -4.23(19) . . . . ? N1 C7 C8 N3 5.5(2) . . . . ? N2 C7 C8 N3 -175.40(17) . . . . ? N1 C7 C8 C9 -173.11(19) . . . . ? N2 C7 C8 C9 6.0(3) . . . . ? N3 C8 C9 C10 -0.4(3) . . . . ? C7 C8 C9 C10 178.0(2) . . . . ? C8 C9 C10 C11 0.5(4) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C8 N3 C12 C11 0.0(3) . . . . ? Zn1 N3 C12 C11 -174.25(14) . . . . ? C8 N3 C12 C13 178.22(15) . . . . ? Zn1 N3 C12 C13 3.9(2) . . . . ? C10 C11 C12 N3 0.1(3) . . . . ? C10 C11 C12 C13 -178.0(2) . . . . ? Zn1 O1 C13 O2 164.99(17) . . . . ? Zn1 O1 C13 C12 -12.67(18) . . . . ? N3 C12 C13 O2 -170.67(17) . . . . ? C11 C12 C13 O2 7.5(3) . . . . ? N3 C12 C13 O1 7.2(2) . . . . ? C11 C12 C13 O1 -174.64(18) . . . . ? C20 N4 C14 C15 -179.68(19) . . . . ? Zn1 N4 C14 C15 -6.5(3) . . . . ? C20 N4 C14 C19 -0.06(19) . . . . ? Zn1 N4 C14 C19 173.13(14) . . . . ? N4 C14 C15 C16 178.56(18) . . . . ? C19 C14 C15 C16 -1.0(3) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C18 2.4(3) . . . . ? C16 C17 C18 C19 -1.6(3) . . . . ? C20 N5 C19 C18 177.6(2) . . . . ? C20 N5 C19 C14 -0.07(19) . . . . ? C17 C18 C19 N5 -177.80(19) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? N4 C14 C19 N5 0.08(19) . . . . ? C15 C14 C19 N5 179.75(16) . . . . ? N4 C14 C19 C18 -177.92(17) . . . . ? C15 C14 C19 C18 1.8(3) . . . . ? C14 N4 C20 N5 0.02(19) . . . . ? Zn1 N4 C20 N5 -175.64(11) . . . . ? C14 N4 C20 C21 178.44(15) . . . . ? Zn1 N4 C20 C21 2.78(19) . . . . ? C19 N5 C20 N4 0.0(2) . . . . ? C19 N5 C20 C21 -178.20(17) . . . . ? C25 N6 C21 C22 0.3(3) . . . . ? Zn1 N6 C21 C22 176.33(13) . . . . ? C25 N6 C21 C20 -179.79(15) . . . . ? Zn1 N6 C21 C20 -3.80(19) . . . . ? N4 C20 C21 N6 0.3(2) . . . . ? N5 C20 C21 N6 178.46(16) . . . . ? N4 C20 C21 C22 -179.82(18) . . . . ? N5 C20 C21 C22 -1.7(3) . . . . ? N6 C21 C22 C23 0.2(3) . . . . ? C20 C21 C22 C23 -179.67(18) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C21 N6 C25 C24 -0.4(3) . . . . ? Zn1 N6 C25 C24 -176.47(14) . . . . ? C21 N6 C25 C26 178.98(15) . . . . ? Zn1 N6 C25 C26 2.9(2) . . . . ? C23 C24 C25 N6 0.0(3) . . . . ? C23 C24 C25 C26 -179.36(19) . . . . ? Zn1 O3 C26 O4 172.8(2) . . . . ? Zn1 O3 C26 C25 -5.0(2) . . . . ? N6 C25 C26 O4 -176.32(19) . . . . ? C24 C25 C26 O4 3.0(3) . . . . ? N6 C25 C26 O3 1.7(2) . . . . ? C24 C25 C26 O3 -178.95(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.843(6) 2.067(9) 2.753(3) 138.1(13) 1_554 O2W H2WB O2W' 0.837(8) 2.168(13) 2.927(7) 150.7(17) . O2W' H2WA' O2W 0.839(7) 2.245(13) 2.927(7) 138.6(11) . N2 H2 O3 0.86 2.13 2.8839(18) 145.3 3_676 N5 H5 O1 0.86 2.10 2.8291(16) 142.0 3_777 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.685 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.075 # Attachment '707899.cif' data_c2 _database_code_depnum_ccdc_archive 'CCDC 707899' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 N3 O4 Zn, 2(H2 O)' _chemical_formula_sum 'C14 H13 N3 O6 Zn' _chemical_formula_weight 384.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.50990(10) _cell_length_b 7.34280(10) _cell_length_c 20.1198(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.8870(10) _cell_angle_gamma 90.00 _cell_volume 1513.58(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4527 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.10 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7013 _exptl_absorpt_correction_T_max 0.7432 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9522 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2736 _reflns_number_gt 2431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+1.5859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2736 _refine_ls_number_parameters 229 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.046 _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 0.55912(3) 0.44989(4) 0.158070(14) 0.03217(12) Uani 1 1 d . . . O1 O 0.52225(17) 0.5915(3) 0.23879(9) 0.0367(4) Uani 1 1 d . . . O2 O 0.35684(18) 0.6948(3) 0.28156(9) 0.0388(4) Uani 1 1 d . . . O3 O 0.72880(18) 0.5452(3) 0.16113(9) 0.0393(5) Uani 1 1 d . . . O4 O 0.91705(19) 0.6521(3) 0.21736(11) 0.0525(6) Uani 1 1 d . . . O1W O 0.1121(2) 0.6618(4) 0.33408(11) 0.0550(6) Uani 1 1 d D . . H1WA H 0.0456(17) 0.666(6) 0.3018(12) 0.083 Uiso 1 1 d D . . H1WB H 0.1822(16) 0.698(6) 0.3251(16) 0.083 Uiso 1 1 d D . . O2W O 0.1192(2) 0.1562(3) 0.90819(11) 0.0547(6) Uani 1 1 d D . . H2WB H 0.118(4) 0.051(2) 0.8914(17) 0.082 Uiso 1 1 d D . . H2WA H 0.104(4) 0.242(3) 0.8796(14) 0.082 Uiso 1 1 d D . . N1 N 0.52561(19) 0.3284(3) 0.06457(10) 0.0275(4) Uani 1 1 d . . . N2 N 0.3731(2) 0.2216(3) -0.02187(10) 0.0311(5) Uani 1 1 d . . . H2 H 0.2973 0.1926 -0.0457 0.037 Uiso 1 1 calc R . . N3 N 0.3712(2) 0.4283(3) 0.13946(10) 0.0280(5) Uani 1 1 d . . . C1 C 0.4027(3) 0.6047(4) 0.24033(12) 0.0316(6) Uani 1 1 d . . . C2 C 0.3091(3) 0.5021(4) 0.18354(13) 0.0313(6) Uani 1 1 d . . . C3 C 0.1756(3) 0.4909(5) 0.17309(15) 0.0440(7) Uani 1 1 d . . . H3 H 0.1319 0.5405 0.2042 0.053 Uiso 1 1 calc R . . C4 C 0.1079(3) 0.4035(5) 0.11470(16) 0.0494(8) Uani 1 1 d . . . H4 H 0.0177 0.3920 0.1071 0.059 Uiso 1 1 calc R . . C5 C 0.1725(3) 0.3330(4) 0.06753(14) 0.0410(7) Uani 1 1 d . . . H5 H 0.1274 0.2771 0.0278 0.049 Uiso 1 1 calc R . . C6 C 0.3075(2) 0.3495(3) 0.08207(12) 0.0296(5) Uani 1 1 d . . . C7 C 0.3992(2) 0.2971(3) 0.04021(12) 0.0280(5) Uani 1 1 d . . . C8 C 0.4909(3) 0.1990(3) -0.04040(12) 0.0313(6) Uani 1 1 d . . . C9 C 0.5226(3) 0.1252(4) -0.09807(13) 0.0387(6) Uani 1 1 d . . . H9 H 0.4586 0.0819 -0.1343 0.046 Uiso 1 1 calc R . . C10 C 0.6528(3) 0.1187(4) -0.09946(15) 0.0441(7) Uani 1 1 d . . . H10 H 0.6775 0.0692 -0.1372 0.053 Uiso 1 1 calc R . . C11 C 0.7493(3) 0.1855(4) -0.04489(15) 0.0440(7) Uani 1 1 d . . . H11 H 0.8364 0.1795 -0.0476 0.053 Uiso 1 1 calc R . . C12 C 0.7183(3) 0.2594(4) 0.01247(14) 0.0371(6) Uani 1 1 d . . . H12 H 0.7827 0.3033 0.0484 0.044 Uiso 1 1 calc R . . C13 C 0.5873(2) 0.2659(3) 0.01455(12) 0.0290(5) Uani 1 1 d . . . C14 C 0.8136(3) 0.5752(4) 0.21451(15) 0.0426(7) Uani 1 1 d . . . H14 H 0.7959 0.5353 0.2554 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.02712(18) 0.0405(2) 0.02718(18) -0.00240(13) 0.00237(12) -0.00203(13) O1 0.0298(10) 0.0495(11) 0.0290(9) -0.0074(8) 0.0025(7) -0.0006(8) O2 0.0372(10) 0.0475(11) 0.0321(9) -0.0112(9) 0.0084(8) -0.0024(9) O3 0.0285(9) 0.0551(13) 0.0330(10) -0.0016(9) 0.0040(8) -0.0102(9) O4 0.0299(10) 0.0710(16) 0.0514(13) -0.0003(11) -0.0018(9) -0.0109(10) O1W 0.0457(12) 0.0688(16) 0.0457(12) -0.0013(12) -0.0003(10) -0.0050(12) O2W 0.0578(14) 0.0578(14) 0.0417(12) -0.0002(11) -0.0033(11) -0.0098(12) N1 0.0283(10) 0.0297(11) 0.0228(10) 0.0007(8) 0.0022(8) -0.0018(9) N2 0.0335(11) 0.0312(11) 0.0251(10) -0.0014(9) -0.0009(9) -0.0056(9) N3 0.0262(10) 0.0310(11) 0.0252(10) -0.0002(9) 0.0022(8) -0.0019(9) C1 0.0329(14) 0.0365(14) 0.0248(12) 0.0019(11) 0.0051(11) -0.0009(11) C2 0.0309(13) 0.0354(14) 0.0274(13) 0.0011(11) 0.0063(11) -0.0014(11) C3 0.0336(15) 0.0611(19) 0.0402(16) -0.0099(14) 0.0144(13) -0.0054(14) C4 0.0262(14) 0.071(2) 0.0512(18) -0.0098(16) 0.0095(13) -0.0132(14) C5 0.0320(14) 0.0518(18) 0.0369(14) -0.0075(13) 0.0030(12) -0.0109(13) C6 0.0301(13) 0.0292(13) 0.0282(12) 0.0009(10) 0.0034(10) -0.0037(11) C7 0.0308(13) 0.0268(12) 0.0241(12) 0.0005(10) 0.0016(10) -0.0039(10) C8 0.0398(14) 0.0263(13) 0.0265(12) 0.0039(10) 0.0045(11) -0.0004(11) C9 0.0550(18) 0.0344(15) 0.0250(13) 0.0006(11) 0.0051(12) -0.0004(13) C10 0.064(2) 0.0370(15) 0.0358(15) 0.0033(13) 0.0200(14) 0.0082(14) C11 0.0475(17) 0.0423(17) 0.0467(17) 0.0095(14) 0.0203(14) 0.0092(14) C12 0.0345(14) 0.0408(16) 0.0349(14) 0.0062(12) 0.0056(11) 0.0021(12) C13 0.0362(13) 0.0267(13) 0.0234(12) 0.0042(10) 0.0048(10) -0.0002(11) C14 0.0337(15) 0.0554(19) 0.0361(15) 0.0022(13) 0.0025(12) -0.0061(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.9040(18) . ? Zn1 N3 1.933(2) . ? Zn1 O1 2.0370(18) . ? Zn1 N1 2.040(2) . ? Zn1 O2 2.2993(19) 2_645 ? O1 C1 1.267(3) . ? O2 O2 0.000(5) 1 ? O2 C1 1.239(3) . ? O2 Zn1 2.2993(19) 2_655 ? O3 C14 1.253(3) . ? O4 C14 1.215(3) . ? O1W H1WA 0.842(10) . ? O1W H1WB 0.840(10) . ? O2W H2WB 0.843(10) . ? O2W H2WA 0.845(10) . ? N1 C7 1.329(3) . ? N1 C13 1.391(3) . ? N2 C7 1.338(3) . ? N2 C8 1.380(3) . ? N2 H2 0.8600 . ? N3 C2 1.328(3) . ? N3 C6 1.331(3) . ? C1 O2 1.239(3) 1 ? C1 C2 1.529(4) . ? C2 C3 1.374(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C6 C7 1.466(4) . ? C8 C9 1.387(4) . ? C8 C13 1.411(3) . ? C9 C10 1.375(4) . ? C9 H9 0.9300 . ? C10 C11 1.406(4) . ? C10 H10 0.9300 . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.388(4) . ? C12 H12 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 N3 161.02(9) . . ? O3 Zn1 O1 97.46(8) . . ? N3 Zn1 O1 80.12(8) . . ? O3 Zn1 N1 99.12(8) . . ? N3 Zn1 N1 80.02(8) . . ? O1 Zn1 N1 159.04(8) . . ? O3 Zn1 O2 92.05(8) . 2_645 ? N3 Zn1 O2 106.91(8) . 2_645 ? O1 Zn1 O2 96.53(7) . 2_645 ? N1 Zn1 O2 95.61(7) . 2_645 ? C1 O1 Zn1 115.11(16) . . ? O2 O2 C1 0(10) 1 . ? O2 O2 Zn1 0(10) 1 2_655 ? C1 O2 Zn1 128.86(17) . 2_655 ? C14 O3 Zn1 125.07(19) . . ? H1WA O1W H1WB 116.1(15) . . ? H2WB O2W H2WA 115.4(14) . . ? C7 N1 C13 105.4(2) . . ? C7 N1 Zn1 111.61(16) . . ? C13 N1 Zn1 143.02(17) . . ? C7 N2 C8 107.0(2) . . ? C7 N2 H2 126.5 . . ? C8 N2 H2 126.5 . . ? C2 N3 C6 122.0(2) . . ? C2 N3 Zn1 118.03(17) . . ? C6 N3 Zn1 119.88(17) . . ? O2 C1 O2 0.00(16) 1 . ? O2 C1 O1 126.4(2) 1 . ? O2 C1 O1 126.4(2) . . ? O2 C1 C2 118.8(2) 1 . ? O2 C1 C2 118.8(2) . . ? O1 C1 C2 114.8(2) . . ? N3 C2 C3 120.7(2) . . ? N3 C2 C1 111.7(2) . . ? C3 C2 C1 127.5(2) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 117.2(3) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? N3 C6 C5 120.9(2) . . ? N3 C6 C7 110.2(2) . . ? C5 C6 C7 128.9(2) . . ? N1 C7 N2 113.3(2) . . ? N1 C7 C6 118.3(2) . . ? N2 C7 C6 128.4(2) . . ? N2 C8 C9 132.1(2) . . ? N2 C8 C13 106.1(2) . . ? C9 C8 C13 121.8(2) . . ? C10 C9 C8 117.1(3) . . ? C10 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 121.8(3) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 117.4(3) . . ? C11 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? C12 C13 N1 131.2(2) . . ? C12 C13 C8 120.6(2) . . ? N1 C13 C8 108.2(2) . . ? O4 C14 O3 125.5(3) . . ? O4 C14 H14 117.3 . . ? O3 C14 H14 117.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C1 159.78(19) . . . . ? N3 Zn1 O1 C1 -1.18(19) . . . . ? N1 Zn1 O1 C1 17.7(3) . . . . ? O2 Zn1 O1 C1 -107.28(19) 2_645 . . . ? N3 Zn1 O3 C14 121.2(3) . . . . ? O1 Zn1 O3 C14 39.9(3) . . . . ? N1 Zn1 O3 C14 -153.0(2) . . . . ? O2 Zn1 O3 C14 -56.9(2) 2_645 . . . ? O3 Zn1 N1 C7 -161.16(17) . . . . ? N3 Zn1 N1 C7 -0.39(17) . . . . ? O1 Zn1 N1 C7 -19.3(3) . . . . ? O2 Zn1 N1 C7 105.84(17) 2_645 . . . ? O3 Zn1 N1 C13 17.6(3) . . . . ? N3 Zn1 N1 C13 178.3(3) . . . . ? O1 Zn1 N1 C13 159.4(2) . . . . ? O2 Zn1 N1 C13 -75.4(3) 2_645 . . . ? O3 Zn1 N3 C2 -86.0(3) . . . . ? O1 Zn1 N3 C2 -1.77(19) . . . . ? N1 Zn1 N3 C2 -175.0(2) . . . . ? O2 Zn1 N3 C2 92.11(19) 2_645 . . . ? O3 Zn1 N3 C6 90.6(3) . . . . ? O1 Zn1 N3 C6 174.8(2) . . . . ? N1 Zn1 N3 C6 1.58(19) . . . . ? O2 Zn1 N3 C6 -91.30(19) 2_645 . . . ? Zn1 O2 C1 O2 0(5) 2_655 . . 1 ? O2 O2 C1 O1 0.0(4) 1 . . . ? Zn1 O2 C1 O1 26.2(4) 2_655 . . . ? O2 O2 C1 C2 0.0(3) 1 . . . ? Zn1 O2 C1 C2 -151.74(18) 2_655 . . . ? Zn1 O1 C1 O2 -174.5(2) . . . 1 ? Zn1 O1 C1 O2 -174.5(2) . . . . ? Zn1 O1 C1 C2 3.5(3) . . . . ? C6 N3 C2 C3 3.6(4) . . . . ? Zn1 N3 C2 C3 -179.9(2) . . . . ? C6 N3 C2 C1 -172.6(2) . . . . ? Zn1 N3 C2 C1 3.9(3) . . . . ? O2 C1 C2 N3 173.4(2) 1 . . . ? O2 C1 C2 N3 173.4(2) . . . . ? O1 C1 C2 N3 -4.8(3) . . . . ? O2 C1 C2 C3 -2.5(4) 1 . . . ? O2 C1 C2 C3 -2.5(4) . . . . ? O1 C1 C2 C3 179.3(3) . . . . ? N3 C2 C3 C4 -1.2(5) . . . . ? C1 C2 C3 C4 174.4(3) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C3 C4 C5 C6 1.6(5) . . . . ? C2 N3 C6 C5 -3.3(4) . . . . ? Zn1 N3 C6 C5 -179.8(2) . . . . ? C2 N3 C6 C7 174.2(2) . . . . ? Zn1 N3 C6 C7 -2.3(3) . . . . ? C4 C5 C6 N3 0.7(4) . . . . ? C4 C5 C6 C7 -176.3(3) . . . . ? C13 N1 C7 N2 -0.8(3) . . . . ? Zn1 N1 C7 N2 178.41(17) . . . . ? C13 N1 C7 C6 -179.9(2) . . . . ? Zn1 N1 C7 C6 -0.7(3) . . . . ? C8 N2 C7 N1 0.5(3) . . . . ? C8 N2 C7 C6 179.5(2) . . . . ? N3 C6 C7 N1 1.9(3) . . . . ? C5 C6 C7 N1 179.1(3) . . . . ? N3 C6 C7 N2 -177.1(2) . . . . ? C5 C6 C7 N2 0.1(5) . . . . ? C7 N2 C8 C9 178.6(3) . . . . ? C7 N2 C8 C13 0.0(3) . . . . ? N2 C8 C9 C10 -178.1(3) . . . . ? C13 C8 C9 C10 0.4(4) . . . . ? C8 C9 C10 C11 -0.5(4) . . . . ? C9 C10 C11 C12 0.3(5) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 N1 178.9(3) . . . . ? C11 C12 C13 C8 -0.1(4) . . . . ? C7 N1 C13 C12 -178.3(3) . . . . ? Zn1 N1 C13 C12 2.9(5) . . . . ? C7 N1 C13 C8 0.8(3) . . . . ? Zn1 N1 C13 C8 -178.0(2) . . . . ? N2 C8 C13 C12 178.7(2) . . . . ? C9 C8 C13 C12 -0.1(4) . . . . ? N2 C8 C13 N1 -0.5(3) . . . . ? C9 C8 C13 N1 -179.3(2) . . . . ? Zn1 O3 C14 O4 -172.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O4 0.842(10) 1.923(13) 2.752(3) 168(3) 1_455 O1W H1WB O2 0.840(10) 2.204(19) 3.001(3) 158(4) 1 O2W H2WB O1W 0.843(10) 1.934(14) 2.762(3) 167(3) 4_566 O2W H2WA O4 0.845(10) 2.07(2) 2.842(3) 153(3) 3_666 O2W H2WA O3 0.845(10) 2.61(3) 3.209(3) 129(4) 3_666 N2 H2 O2W 0.86 1.91 2.767(3) 171.6 1_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.063 # Attachment '707900.cif' data_c3 _database_code_depnum_ccdc_archive 'CCDC 707900' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N3 O3 S Zn, Cl O4, H2 O' _chemical_formula_sum 'C15 H16 Cl N3 O8 S Zn' _chemical_formula_weight 499.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9170(8) _cell_length_b 7.3303(5) _cell_length_c 20.6012(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.3000(10) _cell_angle_gamma 90.00 _cell_volume 1930.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3289 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 22.87 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6678 _exptl_absorpt_correction_T_max 0.7874 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9759 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3580 _reflns_number_gt 2926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+2.0492P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3580 _refine_ls_number_parameters 270 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.043 _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 0.55671(3) 0.93866(6) 0.858992(19) 0.03216(16) Uani 1 1 d . . . S1 S 0.78918(8) 0.86099(15) 0.87279(5) 0.0486(3) Uani 1 1 d . . . Cl1 Cl 0.00955(8) 0.41050(17) 0.86928(5) 0.0532(3) Uani 1 1 d . . . O1 O 0.53743(19) 1.0888(3) 0.77417(11) 0.0357(6) Uani 1 1 d . . . O2 O 0.4106(2) 1.1850(3) 0.69538(11) 0.0393(6) Uani 1 1 d . . . O3 O 0.70304(19) 0.9897(4) 0.88767(13) 0.0442(6) Uani 1 1 d . . . O4 O -0.0990(3) 0.4008(7) 0.86956(18) 0.0893(13) Uani 1 1 d . . . O5 O 0.0416(5) 0.5792(8) 0.8536(3) 0.163(3) Uani 1 1 d . . . O7 O 0.0614(3) 0.3548(8) 0.9307(2) 0.1080(16) Uani 1 1 d . . . O8 O 0.1887(3) 0.6282(7) 0.01124(19) 0.0847(13) Uani 1 1 d D . . H8A H 0.149(4) 0.567(8) -0.017(2) 0.127 Uiso 1 1 d D . . H8B H 0.182(5) 0.607(9) 0.0506(9) 0.127 Uiso 1 1 d D . . N1 N 0.4064(2) 0.9333(3) 0.83794(13) 0.0267(6) Uani 1 1 d . . . N2 N 0.5192(2) 0.8272(4) 0.94372(12) 0.0271(6) Uani 1 1 d . . . N3 N 0.3888(2) 0.7255(4) 0.99339(13) 0.0300(6) Uani 1 1 d . . . H3 H 0.3262 0.6993 0.9999 0.036 Uiso 1 1 calc R . . C1 C 0.4438(3) 1.1005(5) 0.74630(16) 0.0309(7) Uani 1 1 d . . . C2 C 0.3635(3) 1.0015(5) 0.78081(15) 0.0294(7) Uani 1 1 d . . . C3 C 0.2577(3) 0.9853(6) 0.76057(18) 0.0420(9) Uani 1 1 d . . . H3A H 0.2275 1.0314 0.7202 0.050 Uiso 1 1 calc R . . C4 C 0.1973(3) 0.8993(6) 0.8013(2) 0.0482(10) Uani 1 1 d . . . H4 H 0.1258 0.8851 0.7881 0.058 Uiso 1 1 calc R . . C5 C 0.2428(3) 0.8336(6) 0.86223(18) 0.0419(9) Uani 1 1 d . . . H5 H 0.2026 0.7777 0.8906 0.050 Uiso 1 1 calc R . . C6 C 0.3493(3) 0.8541(4) 0.87912(15) 0.0289(7) Uani 1 1 d . . . O6 O 0.0351(4) 0.2897(9) 0.8218(3) 0.135(2) Uani 1 1 d . . . C7 C 0.4167(3) 0.7994(4) 0.93923(15) 0.0278(7) Uani 1 1 d . . . C8 C 0.5613(3) 0.7635(4) 1.00532(15) 0.0275(7) Uani 1 1 d . . . C9 C 0.6639(3) 0.7532(5) 1.03670(17) 0.0356(8) Uani 1 1 d . . . H9 H 0.7193 0.7956 1.0167 0.043 Uiso 1 1 calc R . . C10 C 0.6804(3) 0.6779(5) 1.09845(18) 0.0409(9) Uani 1 1 d . . . H10 H 0.7484 0.6690 1.1204 0.049 Uiso 1 1 calc R . . C11 C 0.5973(3) 0.6141(5) 1.12936(17) 0.0395(9) Uani 1 1 d . . . H11 H 0.6116 0.5644 1.1712 0.047 Uiso 1 1 calc R . . C12 C 0.4953(3) 0.6231(5) 1.09930(16) 0.0365(8) Uani 1 1 d . . . H12 H 0.4403 0.5806 1.1197 0.044 Uiso 1 1 calc R . . C13 C 0.4789(3) 0.6992(4) 1.03677(15) 0.0284(7) Uani 1 1 d . . . C14 C 0.8272(4) 0.9457(9) 0.7996(2) 0.0819(19) Uani 1 1 d . . . H14A H 0.7719 0.9255 0.7638 0.123 Uiso 1 1 calc R . . H14B H 0.8892 0.8837 0.7910 0.123 Uiso 1 1 calc R . . H14C H 0.8410 1.0741 0.8041 0.123 Uiso 1 1 calc R . . C15 C 0.8995(4) 0.9306(7) 0.9290(3) 0.0672(14) Uani 1 1 d . . . H15A H 0.9072 1.0606 0.9268 0.101 Uiso 1 1 calc R . . H15B H 0.9612 0.8726 0.9179 0.101 Uiso 1 1 calc R . . H15C H 0.8897 0.8963 0.9726 0.101 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0296(2) 0.0384(3) 0.0293(2) 0.00084(17) 0.00721(16) -0.00186(17) S1 0.0334(5) 0.0514(6) 0.0600(7) -0.0034(5) 0.0039(4) -0.0029(4) Cl1 0.0368(5) 0.0723(8) 0.0507(6) 0.0011(5) 0.0069(4) -0.0109(5) O1 0.0347(14) 0.0441(15) 0.0303(13) 0.0050(10) 0.0109(10) -0.0040(11) O2 0.0517(16) 0.0383(14) 0.0280(13) 0.0089(11) 0.0063(11) -0.0017(12) O3 0.0291(13) 0.0547(16) 0.0489(16) -0.0098(13) 0.0061(12) -0.0067(12) O4 0.0373(18) 0.160(4) 0.071(2) 0.025(2) 0.0060(16) 0.000(2) O5 0.158(6) 0.107(4) 0.222(7) 0.052(4) 0.022(5) -0.055(4) O7 0.069(3) 0.171(5) 0.076(3) 0.033(3) -0.013(2) -0.012(3) O8 0.063(2) 0.125(3) 0.074(2) -0.033(2) 0.036(2) -0.045(2) N1 0.0295(15) 0.0277(14) 0.0237(13) 0.0003(11) 0.0066(11) -0.0008(11) N2 0.0307(15) 0.0282(14) 0.0232(13) 0.0000(11) 0.0067(11) -0.0004(12) N3 0.0311(15) 0.0336(16) 0.0268(14) 0.0008(12) 0.0093(12) -0.0046(12) C1 0.037(2) 0.0287(17) 0.0284(18) -0.0037(14) 0.0087(15) -0.0012(14) C2 0.0339(18) 0.0297(17) 0.0244(16) 0.0011(14) 0.0037(14) -0.0012(14) C3 0.038(2) 0.052(2) 0.034(2) 0.0079(17) -0.0038(16) -0.0042(18) C4 0.0282(19) 0.067(3) 0.047(2) 0.012(2) -0.0039(17) -0.0093(18) C5 0.033(2) 0.052(2) 0.041(2) 0.0095(18) 0.0074(16) -0.0102(17) C6 0.0307(17) 0.0281(17) 0.0281(17) -0.0021(14) 0.0054(14) -0.0035(14) O6 0.121(4) 0.175(5) 0.116(4) -0.053(4) 0.044(3) 0.014(4) C7 0.0329(18) 0.0262(17) 0.0253(16) -0.0007(13) 0.0077(13) -0.0037(14) C8 0.0346(18) 0.0236(16) 0.0249(16) -0.0034(13) 0.0060(13) 0.0007(14) C9 0.0332(19) 0.039(2) 0.0352(19) -0.0033(16) 0.0062(15) 0.0011(16) C10 0.043(2) 0.041(2) 0.036(2) -0.0053(17) -0.0039(16) 0.0076(17) C11 0.053(2) 0.040(2) 0.0250(18) 0.0030(15) 0.0037(16) 0.0051(18) C12 0.050(2) 0.0332(19) 0.0274(18) 0.0011(15) 0.0109(16) -0.0014(16) C13 0.0359(18) 0.0251(17) 0.0247(16) -0.0048(13) 0.0062(14) -0.0017(14) C14 0.067(3) 0.133(6) 0.051(3) -0.014(3) 0.027(3) -0.029(3) C15 0.037(2) 0.086(4) 0.072(3) 0.007(3) -0.013(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 1.927(3) . ? Zn1 O3 1.934(3) . ? Zn1 N2 2.048(3) . ? Zn1 O1 2.050(2) . ? Zn1 O2 2.242(2) 2_646 ? S1 O3 1.523(3) . ? S1 C14 1.765(5) . ? S1 C15 1.776(4) . ? Cl1 O5 1.358(5) . ? Cl1 O6 1.394(5) . ? Cl1 O4 1.404(3) . ? Cl1 O7 1.404(4) . ? O1 C1 1.264(4) . ? O2 C1 1.240(4) . ? O2 Zn1 2.242(2) 2_656 ? O8 H8A 0.840(10) . ? O8 H8B 0.842(10) . ? N1 C2 1.324(4) . ? N1 C6 1.335(4) . ? N2 C7 1.330(4) . ? N2 C8 1.387(4) . ? N3 C7 1.336(4) . ? N3 C13 1.375(4) . ? N3 H3 0.8600 . ? C1 C2 1.524(5) . ? C2 C3 1.375(5) . ? C3 C4 1.379(6) . ? C3 H3A 0.9300 . ? C4 C5 1.392(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(5) . ? C5 H5 0.9300 . ? C6 C7 1.463(5) . ? C8 C9 1.390(5) . ? C8 C13 1.406(5) . ? C9 C10 1.375(5) . ? C9 H9 0.9300 . ? C10 C11 1.406(5) . ? C10 H10 0.9300 . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 C13 1.392(5) . ? C12 H12 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 O3 168.81(11) . . ? N1 Zn1 N2 80.16(11) . . ? O3 Zn1 N2 99.09(11) . . ? N1 Zn1 O1 79.90(10) . . ? O3 Zn1 O1 98.61(11) . . ? N2 Zn1 O1 157.87(10) . . ? N1 Zn1 O2 97.28(10) . 2_646 ? O3 Zn1 O2 93.84(11) . 2_646 ? N2 Zn1 O2 100.36(10) . 2_646 ? O1 Zn1 O2 91.59(9) . 2_646 ? O3 S1 C14 104.8(2) . . ? O3 S1 C15 103.4(2) . . ? C14 S1 C15 99.2(3) . . ? O5 Cl1 O6 107.4(4) . . ? O5 Cl1 O4 112.7(4) . . ? O6 Cl1 O4 107.9(3) . . ? O5 Cl1 O7 110.9(4) . . ? O6 Cl1 O7 108.5(3) . . ? O4 Cl1 O7 109.2(2) . . ? C1 O1 Zn1 114.5(2) . . ? C1 O2 Zn1 140.3(2) . 2_656 ? S1 O3 Zn1 121.93(16) . . ? H8A O8 H8B 115(3) . . ? C2 N1 C6 122.0(3) . . ? C2 N1 Zn1 118.1(2) . . ? C6 N1 Zn1 119.8(2) . . ? C7 N2 C8 105.5(3) . . ? C7 N2 Zn1 111.0(2) . . ? C8 N2 Zn1 143.5(2) . . ? C7 N3 C13 107.1(3) . . ? C7 N3 H3 126.4 . . ? C13 N3 H3 126.4 . . ? O2 C1 O1 127.5(3) . . ? O2 C1 C2 117.2(3) . . ? O1 C1 C2 115.3(3) . . ? N1 C2 C3 120.5(3) . . ? N1 C2 C1 111.6(3) . . ? C3 C2 C1 127.8(3) . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 117.7(3) . . ? C6 C5 H5 121.1 . . ? C4 C5 H5 121.1 . . ? N1 C6 C5 120.7(3) . . ? N1 C6 C7 110.0(3) . . ? C5 C6 C7 129.4(3) . . ? N2 C7 N3 113.0(3) . . ? N2 C7 C6 118.8(3) . . ? N3 C7 C6 128.2(3) . . ? N2 C8 C9 131.7(3) . . ? N2 C8 C13 108.1(3) . . ? C9 C8 C13 120.1(3) . . ? C10 C9 C8 117.5(3) . . ? C10 C9 H9 121.2 . . ? C8 C9 H9 121.2 . . ? C9 C10 C11 121.7(4) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 121.7(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 116.4(3) . . ? C11 C12 H12 121.8 . . ? C13 C12 H12 121.8 . . ? N3 C13 C12 131.3(3) . . ? N3 C13 C8 106.2(3) . . ? C12 C13 C8 122.4(3) . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Zn1 O1 C1 -3.7(2) . . . . ? O3 Zn1 O1 C1 -172.4(2) . . . . ? N2 Zn1 O1 C1 -29.6(4) . . . . ? O2 Zn1 O1 C1 93.5(2) 2_646 . . . ? C14 S1 O3 Zn1 93.6(3) . . . . ? C15 S1 O3 Zn1 -162.9(2) . . . . ? N1 Zn1 O3 S1 -177.2(5) . . . . ? N2 Zn1 O3 S1 97.59(19) . . . . ? O1 Zn1 O3 S1 -95.7(2) . . . . ? O2 Zn1 O3 S1 -3.5(2) 2_646 . . . ? O3 Zn1 N1 C2 90.6(6) . . . . ? N2 Zn1 N1 C2 177.6(3) . . . . ? O1 Zn1 N1 C2 7.3(2) . . . . ? O2 Zn1 N1 C2 -83.1(2) 2_646 . . . ? O3 Zn1 N1 C6 -92.7(6) . . . . ? N2 Zn1 N1 C6 -5.7(2) . . . . ? O1 Zn1 N1 C6 -176.0(3) . . . . ? O2 Zn1 N1 C6 93.7(2) 2_646 . . . ? N1 Zn1 N2 C7 3.8(2) . . . . ? O3 Zn1 N2 C7 172.5(2) . . . . ? O1 Zn1 N2 C7 29.7(4) . . . . ? O2 Zn1 N2 C7 -91.9(2) 2_646 . . . ? N1 Zn1 N2 C8 -178.6(4) . . . . ? O3 Zn1 N2 C8 -9.9(4) . . . . ? O1 Zn1 N2 C8 -152.7(3) . . . . ? O2 Zn1 N2 C8 85.7(4) 2_646 . . . ? Zn1 O2 C1 O1 -33.5(6) 2_656 . . . ? Zn1 O2 C1 C2 145.2(3) 2_656 . . . ? Zn1 O1 C1 O2 178.7(3) . . . . ? Zn1 O1 C1 C2 0.0(4) . . . . ? C6 N1 C2 C3 -3.0(5) . . . . ? Zn1 N1 C2 C3 173.7(3) . . . . ? C6 N1 C2 C1 174.3(3) . . . . ? Zn1 N1 C2 C1 -9.0(4) . . . . ? O2 C1 C2 N1 -173.2(3) . . . . ? O1 C1 C2 N1 5.7(4) . . . . ? O2 C1 C2 C3 3.9(5) . . . . ? O1 C1 C2 C3 -177.3(4) . . . . ? N1 C2 C3 C4 1.0(6) . . . . ? C1 C2 C3 C4 -175.9(4) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? C3 C4 C5 C6 -1.4(6) . . . . ? C2 N1 C6 C5 2.7(5) . . . . ? Zn1 N1 C6 C5 -173.9(3) . . . . ? C2 N1 C6 C7 -177.4(3) . . . . ? Zn1 N1 C6 C7 6.0(4) . . . . ? C4 C5 C6 N1 -0.5(6) . . . . ? C4 C5 C6 C7 179.7(4) . . . . ? C8 N2 C7 N3 1.0(4) . . . . ? Zn1 N2 C7 N3 179.6(2) . . . . ? C8 N2 C7 C6 179.7(3) . . . . ? Zn1 N2 C7 C6 -1.8(4) . . . . ? C13 N3 C7 N2 -1.0(4) . . . . ? C13 N3 C7 C6 -179.5(3) . . . . ? N1 C6 C7 N2 -2.4(4) . . . . ? C5 C6 C7 N2 177.4(4) . . . . ? N1 C6 C7 N3 176.0(3) . . . . ? C5 C6 C7 N3 -4.2(6) . . . . ? C7 N2 C8 C9 178.4(4) . . . . ? Zn1 N2 C8 C9 0.7(6) . . . . ? C7 N2 C8 C13 -0.6(3) . . . . ? Zn1 N2 C8 C13 -178.3(3) . . . . ? N2 C8 C9 C10 -178.6(3) . . . . ? C13 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C7 N3 C13 C12 -178.1(3) . . . . ? C7 N3 C13 C8 0.6(4) . . . . ? C11 C12 C13 N3 178.7(3) . . . . ? C11 C12 C13 C8 0.2(5) . . . . ? N2 C8 C13 N3 0.0(4) . . . . ? C9 C8 C13 N3 -179.1(3) . . . . ? N2 C8 C13 C12 178.9(3) . . . . ? C9 C8 C13 C12 -0.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H8A O7 0.840(10) 2.13(2) 2.947(6) 165(6) 1_554 O8 H8B O4 0.842(10) 2.09(3) 2.871(5) 154(7) 3_566 N3 H3 O8 0.86 1.90 2.756(4) 176.5 1_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.441 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.081