#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223381.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2223381 loop_ _publ_author_name 'Xu, Wen' 'Zhu, Da-Sheng' 'Song, Xiao-Dan' 'An, Zhe' _publ_section_title ;Poly[[bis[\m~2~-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]zinc(II)] dihydrate] ; _journal_coeditor_code HB5062 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m1223 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac '[Zn (C14 H16 N5 O3)2], 2H2 O' _chemical_formula_moiety '(C28 H32 N10 O6 Zn), 2(H2 O)' _chemical_formula_sum 'C28 H36 N10 O8 Zn' _chemical_formula_weight 704.05 _chemical_name_systematic ;Poly[[bis[\m~2~-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]zinc(II)] dihydrate] ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.10(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.1146(12) _cell_length_b 21.424(4) _cell_length_c 12.577(3) _cell_measurement_temperature 295(2) _cell_volume 1616.8(6) _computing_cell_refinement 'RAPID-AUTO (Rigaku , 1998)' _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15697 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 3.30 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_T_max 0.866 _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrystalStructure; Rigaku/MSC, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.831 _refine_diff_density_min -0.831 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3684 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0565 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1254P)^2^+1.7801P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1577 _refine_ls_wR_factor_ref 0.2095 _reflns_number_gt 2570 _reflns_number_total 3684 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file hb5062.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1616.9(6) _cod_database_code 2223381 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' 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1W -0.045(3) -0.0632(10) -0.0746(11) 0.187(8) Uani d P 0.50 . . O O2W 0.340(5) 0.0205(10) -0.0364(12) 0.251(14) Uani d P 0.50 . . Zn Zn1 0.5000 0.0000 0.5000 0.0265(2) Uani d S 1 . . O O1 0.6981(4) -0.00325(10) 0.3877(2) 0.0271(6) Uani d . 1 . . O O2 0.8573(7) 0.01818(18) 0.2500(3) 0.0616(11) Uani d . 1 . . O O3 0.3495(5) 0.07935(11) 0.4179(2) 0.0317(6) Uani d . 1 . . N N1 0.4916(7) 0.17173(17) 0.1532(3) 0.0481(10) Uani d . 1 . . N N2 0.2252(6) 0.24690(15) 0.1677(3) 0.0386(8) Uani d . 1 . . N N3 -0.0127(6) 0.23572(16) 0.2988(3) 0.0436(9) Uani d . 1 . . N N4 -0.0227(6) 0.32384(15) 0.1907(3) 0.0349(8) Uani d . 1 . . N N5 -0.2450(5) 0.43908(14) 0.1084(2) 0.0273(7) Uani d D 1 . . H H5N -0.154(8) 0.466(2) 0.152(4) 0.065(16) Uiso d D 1 . . C C1 0.7147(7) 0.02891(17) 0.3064(3) 0.0316(8) Uani d . 1 . . C C2 0.5658(7) 0.08450(17) 0.2772(3) 0.0317(8) Uani d . 1 . . C C3 0.3947(6) 0.10453(16) 0.3346(3) 0.0271(7) Uani d . 1 . . C C4 0.2744(7) 0.15974(16) 0.2910(3) 0.0303(8) Uani d . 1 . . C C5 0.0937(8) 0.18359(19) 0.3318(3) 0.0398(10) Uani d . 1 . . H H5 0.0454 0.1610 0.3861 0.048 Uiso calc R 1 . . C C6 0.0671(7) 0.26762(18) 0.2197(3) 0.0327(8) Uani d . 1 . . C C7 0.3246(7) 0.19340(18) 0.2034(3) 0.0360(9) Uani d . 1 . . C C8 0.6010(8) 0.1189(2) 0.1902(4) 0.0457(11) Uani d . 1 . . H H8 0.7096 0.1047 0.1535 0.055 Uiso calc R 1 . . C C9 0.5540(11) 0.2051(3) 0.0585(5) 0.0665(16) Uani d . 1 . . H H9B 0.5306 0.2496 0.0653 0.080 Uiso calc R 1 . . H H9A 0.7107 0.1983 0.0582 0.080 Uiso calc R 1 . . C C10 0.4247(16) 0.1834(5) -0.0401(7) 0.116(3) Uani d . 1 . . H H10C 0.4566 0.1401 -0.0496 0.174 Uiso calc R 1 . . H H10B 0.4605 0.2071 -0.0993 0.174 Uiso calc R 1 . . H H10A 0.2693 0.1883 -0.0385 0.174 Uiso calc R 1 . . C C11 -0.1608(8) 0.3572(2) 0.2553(4) 0.0475(11) Uani d . 1 . . H H11B -0.0673 0.3839 0.3077 0.057 Uiso calc R 1 . . H H11A -0.2346 0.3275 0.2947 0.057 Uiso calc R 1 . . C C12 -0.3356(7) 0.3970(2) 0.1813(4) 0.0398(10) Uani d . 1 . . H H12B -0.4429 0.3694 0.1379 0.048 Uiso calc R 1 . . H H12A -0.4150 0.4218 0.2262 0.048 Uiso calc R 1 . . C C13 -0.1090(6) 0.40176(17) 0.0469(3) 0.0317(8) Uani d . 1 . . H H13A -0.0405 0.4295 0.0018 0.038 Uiso calc R 1 . . H H13B -0.2057 0.3734 -0.0006 0.038 Uiso calc R 1 . . C C14 0.0708(7) 0.36460(18) 0.1185(4) 0.0369(9) Uani d . 1 . . H H14B 0.1500 0.3397 0.0737 0.044 Uiso calc R 1 . . H H14A 0.1768 0.3929 0.1610 0.044 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1W 0.209(18) 0.28(2) 0.094(9) -0.004(16) 0.091(11) 0.013(12) O2W 0.47(4) 0.202(17) 0.077(9) 0.11(2) 0.049(16) -0.057(12) Zn1 0.0317(4) 0.0194(3) 0.0294(3) 0.0006(2) 0.0079(2) 0.0028(2) O1 0.0276(13) 0.0218(12) 0.0333(14) 0.0019(9) 0.0089(10) 0.0029(10) O2 0.073(3) 0.062(2) 0.060(2) 0.040(2) 0.0387(19) 0.0275(18) O3 0.0378(15) 0.0223(12) 0.0368(14) 0.0092(10) 0.0116(11) 0.0121(11) N1 0.065(3) 0.0398(19) 0.046(2) 0.0223(18) 0.0265(19) 0.0195(17) N2 0.051(2) 0.0282(16) 0.0400(18) 0.0135(15) 0.0160(16) 0.0124(14) N3 0.044(2) 0.0361(18) 0.055(2) 0.0166(16) 0.0219(17) 0.0231(17) N4 0.0390(19) 0.0283(16) 0.0415(18) 0.0096(14) 0.0177(15) 0.0119(14) N5 0.0265(16) 0.0219(14) 0.0324(15) 0.0064(12) 0.0028(12) 0.0034(13) C1 0.037(2) 0.0274(18) 0.0316(18) 0.0046(15) 0.0112(16) -0.0002(16) C2 0.038(2) 0.0238(17) 0.0354(19) 0.0070(15) 0.0110(16) 0.0035(15) C3 0.0283(18) 0.0219(16) 0.0302(17) 0.0007(13) 0.0032(14) 0.0013(14) C4 0.036(2) 0.0242(17) 0.0318(18) 0.0021(15) 0.0087(15) 0.0055(15) C5 0.048(3) 0.033(2) 0.043(2) 0.0088(18) 0.0188(19) 0.0174(18) C6 0.033(2) 0.0273(18) 0.0380(19) 0.0046(15) 0.0078(16) 0.0077(16) C7 0.044(2) 0.0323(19) 0.0347(19) 0.0092(17) 0.0137(17) 0.0067(17) C8 0.060(3) 0.037(2) 0.046(2) 0.018(2) 0.026(2) 0.0107(19) C9 0.083(4) 0.063(3) 0.062(3) 0.030(3) 0.038(3) 0.024(3) C10 0.117(7) 0.144(9) 0.090(5) 0.031(6) 0.028(5) 0.024(6) C11 0.055(3) 0.045(2) 0.047(2) 0.025(2) 0.021(2) 0.020(2) C12 0.040(2) 0.036(2) 0.047(2) 0.0157(17) 0.0179(18) 0.0161(19) C13 0.035(2) 0.0247(17) 0.0366(19) 0.0101(15) 0.0094(16) 0.0081(15) C14 0.033(2) 0.0293(18) 0.051(2) 0.0043(16) 0.0147(17) 0.0119(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 O1 . 2.031(3) y Zn1 O1 3_656 2.031(3) ? Zn1 O3 3_656 2.107(2) ? Zn1 O3 . 2.107(2) y Zn1 N5 2_545 2.275(3) ? Zn1 N5 4_666 2.275(3) y O1 C1 . 1.253(5) ? O2 C1 . 1.247(5) ? O3 C3 . 1.256(4) ? N1 C8 . 1.351(5) ? N1 C7 . 1.381(5) ? N1 C9 . 1.500(6) ? N2 C7 . 1.334(5) ? N2 C6 . 1.343(5) ? N3 C5 . 1.319(5) ? N3 C6 . 1.373(5) ? N4 C6 . 1.345(5) ? N4 C14 . 1.454(5) ? N4 C11 . 1.466(5) ? N5 C12 . 1.468(5) ? N5 C13 . 1.475(5) ? N5 Zn1 2 2.275(3) ? N5 H5N . 0.900(10) ? C1 C2 . 1.501(5) ? C2 C8 . 1.370(6) ? C2 C3 . 1.446(5) ? C3 C4 . 1.444(5) ? C4 C7 . 1.399(5) ? C4 C5 . 1.401(6) ? C5 H5 . 0.9300 ? C8 H8 . 0.9300 ? C9 C10 . 1.415(11) ? C9 H9B . 0.9700 ? C9 H9A . 0.9700 ? C10 H10C . 0.9600 ? C10 H10B . 0.9600 ? C10 H10A . 0.9600 ? C11 C12 . 1.534(5) ? C11 H11B . 0.9700 ? C11 H11A . 0.9700 ? C12 H12B . 0.9700 ? C12 H12A . 0.9700 ? C13 C14 . 1.508(5) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 H14B . 0.9700 ? C14 H14A . 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Zn1 O1 . 3_656 180.0 ? O1 Zn1 O3 . 3_656 92.90(10) ? O1 Zn1 O3 3_656 3_656 87.10(10) ? O1 Zn1 O3 . . 87.10(10) ? O1 Zn1 O3 3_656 . 92.90(10) ? O3 Zn1 O3 3_656 . 180.0 ? O1 Zn1 N5 . 2_545 89.74(11) ? O1 Zn1 N5 3_656 2_545 90.26(11) ? O3 Zn1 N5 3_656 2_545 90.86(11) ? O3 Zn1 N5 . 2_545 89.14(11) ? O1 Zn1 N5 . 4_666 90.26(11) ? O1 Zn1 N5 3_656 4_666 89.74(11) ? O3 Zn1 N5 3_656 4_666 89.14(11) ? O3 Zn1 N5 . 4_666 90.86(11) ? N5 Zn1 N5 2_545 4_666 180.0 ? C1 O1 Zn1 . . 134.5(2) ? C3 O3 Zn1 . . 127.6(2) ? C8 N1 C7 . . 119.0(3) ? C8 N1 C9 . . 119.2(4) ? C7 N1 C9 . . 121.8(4) ? C7 N2 C6 . . 116.3(3) ? C5 N3 C6 . . 115.3(4) ? C6 N4 C14 . . 121.2(3) ? C6 N4 C11 . . 122.4(3) ? C14 N4 C11 . . 113.0(3) ? C12 N5 C13 . . 108.3(3) ? C12 N5 Zn1 . 2 115.4(2) ? C13 N5 Zn1 . 2 112.8(2) ? C12 N5 H5N . . 106(4) ? C13 N5 H5N . . 108(4) ? Zn1 N5 H5N 2 . 106(4) ? O2 C1 O1 . . 122.6(4) ? O2 C1 C2 . . 117.7(3) ? O1 C1 C2 . . 119.7(3) ? C8 C2 C3 . . 118.6(3) ? C8 C2 C1 . . 116.2(3) ? C3 C2 C1 . . 125.2(3) ? O3 C3 C4 . . 119.4(3) ? O3 C3 C2 . . 125.8(3) ? C4 C3 C2 . . 114.7(3) ? C7 C4 C5 . . 114.1(3) ? C7 C4 C3 . . 123.2(4) ? C5 C4 C3 . . 122.6(3) ? N3 C5 C4 . . 124.7(4) ? N3 C5 H5 . . 117.6 ? C4 C5 H5 . . 117.6 ? N2 C6 N4 . . 117.3(3) ? N2 C6 N3 . . 125.3(4) ? N4 C6 N3 . . 117.3(4) ? N2 C7 N1 . . 117.6(3) ? N2 C7 C4 . . 123.6(4) ? N1 C7 C4 . . 118.7(3) ? N1 C8 C2 . . 125.6(4) ? N1 C8 H8 . . 117.2 ? C2 C8 H8 . . 117.2 ? C10 C9 N1 . . 110.8(7) ? C10 C9 H9B . . 109.5 ? N1 C9 H9B . . 109.5 ? C10 C9 H9A . . 109.5 ? N1 C9 H9A . . 109.5 ? H9B C9 H9A . . 108.1 ? C9 C10 H10C . . 109.5 ? C9 C10 H10B . . 109.5 ? H10C C10 H10B . . 109.5 ? C9 C10 H10A . . 109.5 ? H10C C10 H10A . . 109.5 ? H10B C10 H10A . . 109.5 ? N4 C11 C12 . . 110.0(3) ? N4 C11 H11B . . 109.7 ? C12 C11 H11B . . 109.7 ? N4 C11 H11A . . 109.7 ? C12 C11 H11A . . 109.7 ? H11B C11 H11A . . 108.2 ? N5 C12 C11 . . 114.7(3) ? N5 C12 H12B . . 108.6 ? C11 C12 H12B . . 108.6 ? N5 C12 H12A . . 108.6 ? C11 C12 H12A . . 108.6 ? H12B C12 H12A . . 107.6 ? N5 C13 C14 . . 113.1(3) ? N5 C13 H13A . . 109.0 ? C14 C13 H13A . . 109.0 ? N5 C13 H13B . . 109.0 ? C14 C13 H13B . . 109.0 ? H13A C13 H13B . . 107.8 ? N4 C14 C13 . . 111.2(3) ? N4 C14 H14B . . 109.4 ? C13 C14 H14B . . 109.4 ? N4 C14 H14A . . 109.4 ? C13 C14 H14A . . 109.4 ? H14B C14 H14A . . 108.0 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 Zn1 O1 C1 3_656 . . . -50(2) ? O3 Zn1 O1 C1 3_656 . . . 179.5(4) ? O3 Zn1 O1 C1 . . . . -0.5(4) ? N5 Zn1 O1 C1 2_545 . . . 88.7(4) ? N5 Zn1 O1 C1 4_666 . . . -91.3(4) ? O1 Zn1 O3 C3 . . . . 0.4(3) ? O1 Zn1 O3 C3 3_656 . . . -179.6(3) ? O3 Zn1 O3 C3 3_656 . . . 7E1(10) ? N5 Zn1 O3 C3 2_545 . . . -89.4(3) ? N5 Zn1 O3 C3 4_666 . . . 90.6(3) ? Zn1 O1 C1 O2 . . . . 178.2(3) ? Zn1 O1 C1 C2 . . . . 1.0(6) ? O2 C1 C2 C8 . . . . -0.1(6) ? O1 C1 C2 C8 . . . . 177.1(4) ? O2 C1 C2 C3 . . . . -178.8(4) ? O1 C1 C2 C3 . . . . -1.6(6) ? Zn1 O3 C3 C4 . . . . -179.0(2) ? Zn1 O3 C3 C2 . . . . -1.1(5) ? C8 C2 C3 O3 . . . . -177.0(4) ? C1 C2 C3 O3 . . . . 1.7(6) ? C8 C2 C3 C4 . . . . 1.0(6) ? C1 C2 C3 C4 . . . . 179.7(4) ? O3 C3 C4 C7 . . . . 175.2(4) ? C2 C3 C4 C7 . . . . -2.9(6) ? O3 C3 C4 C5 . . . . -6.0(6) ? C2 C3 C4 C5 . . . . 175.9(4) ? C6 N3 C5 C4 . . . . -0.8(7) ? C7 C4 C5 N3 . . . . -5.2(7) ? C3 C4 C5 N3 . . . . 175.9(4) ? C7 N2 C6 N4 . . . . 174.8(4) ? C7 N2 C6 N3 . . . . -6.2(7) ? C14 N4 C6 N2 . . . . -9.3(6) ? C11 N4 C6 N2 . . . . -167.0(4) ? C14 N4 C6 N3 . . . . 171.7(4) ? C11 N4 C6 N3 . . . . 14.0(6) ? C5 N3 C6 N2 . . . . 7.0(7) ? C5 N3 C6 N4 . . . . -174.0(4) ? C6 N2 C7 N1 . . . . -178.5(4) ? C6 N2 C7 C4 . . . . -1.0(6) ? C8 N1 C7 N2 . . . . 177.5(4) ? C9 N1 C7 N2 . . . . -2.7(7) ? C8 N1 C7 C4 . . . . -0.1(7) ? C9 N1 C7 C4 . . . . 179.7(5) ? C5 C4 C7 N2 . . . . 6.2(6) ? C3 C4 C7 N2 . . . . -174.9(4) ? C5 C4 C7 N1 . . . . -176.3(4) ? C3 C4 C7 N1 . . . . 2.5(6) ? C7 N1 C8 C2 . . . . -1.9(8) ? C9 N1 C8 C2 . . . . 178.3(5) ? C3 C2 C8 N1 . . . . 1.4(7) ? C1 C2 C8 N1 . . . . -177.4(4) ? C8 N1 C9 C10 . . . . 90.7(7) ? C7 N1 C9 C10 . . . . -89.1(7) ? C6 N4 C11 C12 . . . . -148.9(4) ? C14 N4 C11 C12 . . . . 51.8(5) ? C13 N5 C12 C11 . . . . 53.7(5) ? Zn1 N5 C12 C11 2 . . . -178.8(3) ? N4 C11 C12 N5 . . . . -52.7(5) ? C12 N5 C13 C14 . . . . -55.0(4) ? Zn1 N5 C13 C14 2 . . . 176.0(2) ? C6 N4 C14 C13 . . . . 145.9(4) ? C11 N4 C14 C13 . . . . -54.5(5) ? N5 C13 C14 N4 . . . . 56.5(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N5 H5N O2 2_655 0.91(5) 2.28(5) 3.168(5) 166(4)