#------------------------------------------------------------------------------ #$Date: 2023-03-09 12:19:53 +0200 (Thu, 09 Mar 2023) $ #$Revision: 281771 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106898.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8106898 loop_ _publ_author_name 'Jian, Shou-Jun' 'Liang, Zhen' 'Yang, Yan-Qiu' 'Yang, Huai-Xia' _publ_section_title ; Crystal structure of catena-poly[diaqua-bis(benzene-1,2,4,5-tetracarboxylato-\kN)(m2-2-(1H-1,2,4-trizol-1-ylmethyl)-1H-3,1-benzimidazol-3-ium-\k2 O:O′)zinc(II)] dihydrate, C30H30N10O12Zn ; _journal_issue 2 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 431 _journal_page_last 433 _journal_paper_doi 10.1515/ncrs-2015-0111 _journal_volume 231 _journal_year 2016 _chemical_formula_sum 'C30 H30 N10 O12 Zn' _chemical_formula_weight 788.01 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.86(3) _cell_angle_beta 107.87(3) _cell_angle_gamma 100.22(3) _cell_formula_units_Z 1 _cell_length_a 7.6409(15) _cell_length_b 10.438(2) _cell_length_c 11.246(2) _cell_measurement_reflns_used 2819 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.8684 _cell_measurement_theta_min 1.9078 _cell_volume 837.8(3) _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Rigaku Saturn' _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 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10469 _diffrn_reflns_theta_full 27.87 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_min 1.91 _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_T_max 0.8947 _exptl_absorpt_correction_T_min 0.8543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku/MSC Inc., 2006)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 406 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.349 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 3947 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.989 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0377 _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^)+(0.0336P)^2^+0.4960P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0819 _reflns_number_gt 3587 _reflns_number_total 3947 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL p in P-1 New: P-1 CELL 0.71073 7.6409 10.4380 11.2460 90.860 107.870 100.220 ZERR 1 0.0015 0.0020 0.0020 0.030 0.030 0.030 LATT 1 SFAC C H N O Zn UNIT 30 30 10 12 1 L.S. 20 ACTA BOND $H FMAP 2 PLAN 20 CONF conf size 0.20 0.18 0.14 omit 5 -1 9 htab temp 20 EQIV $1 -x+1, -y+1, -z+2 EQIV $3 x+1, y, z EQIV $5 x+1, y+1, z HTAB O6 O3 HTAB O6 O1 HTAB O5 O2_$1 HTAB O5 O3_$3 HTAB N5 O4_$3 HTAB N4 O6_$5 WGHT 0.033600 0.496000 FVAR 0.86826 ZN1 5 0.500000 0.500000 1.000000 10.50000 0.02119 0.03118 = 0.01546 0.00271 0.00447 0.00480 N1 3 0.649373 0.678564 0.956505 11.00000 0.02771 0.03221 = 0.02218 0.00356 0.00760 0.00359 N2 3 0.728757 0.891557 0.928772 11.00000 0.04379 0.03428 = 0.04173 0.00551 0.01880 0.01141 N3 3 0.834316 0.819217 0.888360 11.00000 0.03208 0.02940 = 0.02654 0.00317 0.01250 0.00447 N4 3 0.890829 1.027328 0.656128 11.00000 0.04006 0.02576 = 0.03347 0.00239 0.01256 -0.00003 AFIX 43 H4B 2 0.954674 1.097578 0.700794 11.00000 -1.20000 AFIX 0 N5 3 0.766737 0.822407 0.603561 11.00000 0.04050 0.02481 = 0.03379 0.00179 0.01261 -0.00091 AFIX 43 H5A 2 0.737688 0.739648 0.608519 11.00000 -1.20000 AFIX 0 O1 4 0.306762 0.477086 0.817584 11.00000 0.02554 0.03725 = 0.01595 0.00173 0.00082 0.01043 O2 4 0.132805 0.625670 0.826306 11.00000 0.04559 0.04932 = 0.01995 -0.00370 0.00144 0.02386 O3 4 -0.225912 0.411928 0.735134 11.00000 0.04595 0.03945 = 0.03312 0.01493 0.02588 0.01523 O4 4 -0.339102 0.581077 0.646702 11.00000 0.02392 0.03025 = 0.03278 0.00084 0.01227 0.00565 O5 4 0.652160 0.382011 0.934678 11.00000 0.03029 0.04834 = 0.01935 0.00521 0.00977 0.01343 O6 4 0.019964 0.247831 0.792938 11.00000 0.04420 0.02887 = 0.06069 -0.00177 -0.00230 0.00518 C1 1 0.181559 0.542447 0.769586 11.00000 0.02063 0.02802 = 0.01476 0.00255 0.00387 0.00196 C2 1 0.084999 0.516447 0.629679 11.00000 0.02006 0.02579 = 0.01467 0.00368 0.00371 0.00423 C3 1 -0.108732 0.505354 0.578415 11.00000 0.02015 0.02471 = 0.01639 0.00316 0.00631 0.00402 C4 1 -0.192444 0.490038 0.448947 11.00000 0.01680 0.03097 = 0.01732 0.00358 0.00277 0.00526 AFIX 43 H4A 2 -0.321217 0.484121 0.414994 11.00000 -1.20000 AFIX 0 C5 1 -0.233486 0.499882 0.660162 11.00000 0.02072 0.02692 = 0.01936 -0.00121 0.00662 -0.00044 C6 1 0.785625 0.693645 0.906262 11.00000 0.03040 0.02883 = 0.02111 0.00205 0.00701 0.00381 AFIX 43 H6A 2 0.839798 0.626727 0.886253 11.00000 -1.20000 AFIX 0 C7 1 0.621237 0.802081 0.968747 11.00000 0.03761 0.04101 = 0.03625 0.00551 0.01828 0.01109 AFIX 43 H7A 2 0.532034 0.821856 1.003051 11.00000 -1.20000 AFIX 0 C8 1 0.967762 0.877816 0.827069 11.00000 0.02988 0.03431 = 0.03231 0.00620 0.01131 0.00137 AFIX 23 H8A 2 1.051458 0.818459 0.825383 11.00000 -1.20000 H8B 2 1.042681 0.957624 0.875098 11.00000 -1.20000 AFIX 0 C9 1 0.873006 0.908066 0.696506 11.00000 0.03111 0.02722 = 0.03242 0.00321 0.01561 0.00215 C10 1 0.709919 0.888683 0.496521 11.00000 0.03761 0.03843 = 0.03073 0.00467 0.01254 0.00307 C11 1 0.596066 0.847262 0.375267 11.00000 0.05421 0.05797 = 0.03871 -0.00279 0.01010 -0.00062 AFIX 43 H11A 2 0.542525 0.759849 0.351338 11.00000 -1.20000 AFIX 0 C12 1 0.566873 0.942781 0.292472 11.00000 0.06047 0.08962 = 0.03427 0.01119 0.00427 0.01115 AFIX 43 H12A 2 0.489953 0.919012 0.210547 11.00000 -1.20000 AFIX 0 C13 1 0.647941 1.073487 0.326560 11.00000 0.06416 0.07639 = 0.04558 0.02874 0.01253 0.01881 AFIX 43 H13A 2 0.624225 1.134221 0.266821 11.00000 -1.20000 AFIX 0 C14 1 0.761421 1.115185 0.445313 11.00000 0.05911 0.04662 = 0.05005 0.01978 0.01757 0.01290 AFIX 43 H14A 2 0.816784 1.202493 0.468143 11.00000 -1.20000 AFIX 0 C15 1 0.789449 1.019335 0.530286 11.00000 0.03779 0.03633 = 0.03402 0.00751 0.01244 0.00653 H1W 2 0.737900 0.372260 0.997353 11.00000 0.05190 H2W 2 0.686100 0.397973 0.869437 11.00000 0.06358 H3W 2 -0.062029 0.297653 0.775098 11.00000 0.05902 H4W 2 0.116935 0.287608 0.794402 11.00000 0.06269 HKLF 4 REM p in P-1 New: P-1 REM R1 = 0.0377 for 3587 Fo > 4sig(Fo) and 0.0420 for all 3947 data REM 257 parameters refined using 0 restraints END WGHT 0.0305 0.3511 REM Highest difference peak 0.349, deepest hole -0.282, 1-sigma level 0.055 Q1 1 -0.1684 0.5016 0.6178 11.00000 0.05 0.35 Q2 1 -0.0157 0.5119 0.6034 11.00000 0.05 0.31 Q3 1 0.1130 0.5095 0.6937 11.00000 0.05 0.29 Q4 1 -0.1419 0.4872 0.5187 11.00000 0.05 0.27 Q5 1 0.0101 0.2603 0.7144 11.00000 0.05 0.23 Q6 1 0.7791 0.9454 0.5044 11.00000 0.05 0.23 Q7 1 0.6082 0.6232 0.9763 11.00000 0.05 0.21 Q8 1 0.1337 0.5147 0.5916 11.00000 0.05 0.21 Q9 1 0.9138 0.8884 0.7566 11.00000 0.05 0.20 Q10 1 0.1385 0.5821 0.8597 11.00000 0.05 0.20 Q11 1 0.7431 0.8542 0.5385 11.00000 0.05 0.19 Q12 1 0.8607 0.9599 0.6902 11.00000 0.05 0.18 Q13 1 0.8948 0.8433 0.8657 11.00000 0.05 0.17 Q14 1 0.7147 0.6620 0.9421 11.00000 0.05 0.17 Q15 1 -0.1651 0.3627 0.7335 11.00000 0.05 0.17 Q16 1 0.6880 0.8742 0.4407 11.00000 0.05 0.17 Q17 1 -0.0843 0.3635 0.5986 11.00000 0.05 0.17 Q18 1 0.9768 1.3139 0.4260 11.00000 0.05 0.17 Q19 1 0.9155 0.6378 1.0406 11.00000 0.05 0.16 Q20 1 0.5531 0.7162 0.8125 11.00000 0.05 0.16 ; _cod_data_source_file suppl_ncrs-2015-0111_suppl.cif _cod_data_source_block p _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. data item '_symmetry_cell_setting' value 'Triclinic' was changed to 'triclinic' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 8106898 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.5000 0.5000 1.0000 0.02292(9) Uani 1 2 d S . . N1 N 0.6494(2) 0.67856(16) 0.95651(14) 0.0277(3) Uani 1 1 d . . . N2 N 0.7288(3) 0.89156(17) 0.92877(17) 0.0382(4) Uani 1 1 d . . . N3 N 0.8343(2) 0.81922(16) 0.88836(15) 0.0288(3) Uani 1 1 d . . . N4 N 0.8908(2) 1.02733(16) 0.65613(16) 0.0337(4) Uani 1 1 d . . . H4B H 0.9547 1.0976 0.7008 0.040 Uiso 1 1 calc R . . N5 N 0.7667(2) 0.82241(16) 0.60356(16) 0.0337(4) Uani 1 1 d . . . H5A H 0.7377 0.7396 0.6085 0.040 Uiso 1 1 calc R . . O1 O 0.30676(17) 0.47709(13) 0.81758(11) 0.0270(3) Uani 1 1 d . . . O2 O 0.1328(2) 0.62567(15) 0.82631(12) 0.0385(4) Uani 1 1 d . . . O3 O -0.2259(2) 0.41193(14) 0.73513(13) 0.0354(3) Uani 1 1 d . . . O4 O -0.33910(17) 0.58108(13) 0.64670(12) 0.0282(3) Uani 1 1 d . . . O5 O 0.6522(2) 0.38201(15) 0.93468(14) 0.0314(3) Uani 1 1 d . . . O6 O 0.0200(3) 0.24783(16) 0.79294(18) 0.0492(4) Uani 1 1 d . . . C1 C 0.1816(2) 0.54245(17) 0.76959(15) 0.0219(3) Uani 1 1 d . . . C2 C 0.0850(2) 0.51645(17) 0.62968(15) 0.0206(3) Uani 1 1 d . . . C3 C -0.1087(2) 0.50535(17) 0.57841(15) 0.0203(3) Uani 1 1 d . . . C4 C -0.1924(2) 0.49004(17) 0.44895(16) 0.0222(3) Uani 1 1 d . . . H4A H -0.3212 0.4841 0.4150 0.027 Uiso 1 1 calc R . . C5 C -0.2335(2) 0.49988(17) 0.66016(16) 0.0229(4) Uani 1 1 d . . . C6 C 0.7856(3) 0.69364(18) 0.90626(17) 0.0273(4) Uani 1 1 d . . . H6A H 0.8398 0.6267 0.8863 0.033 Uiso 1 1 calc R . . C7 C 0.6212(3) 0.8021(2) 0.9687(2) 0.0363(5) Uani 1 1 d . . . H7A H 0.5320 0.8219 1.0031 0.044 Uiso 1 1 calc R . . C8 C 0.9678(3) 0.8778(2) 0.82707(19) 0.0324(4) Uani 1 1 d . . . H8A H 1.0515 0.8185 0.8254 0.039 Uiso 1 1 calc R . . H8B H 1.0427 0.9576 0.8751 0.039 Uiso 1 1 calc R . . C9 C 0.8730(3) 0.90807(18) 0.69651(18) 0.0294(4) Uani 1 1 d . . . C10 C 0.7099(3) 0.8887(2) 0.4965(2) 0.0357(5) Uani 1 1 d . . . C11 C 0.5961(4) 0.8473(3) 0.3753(2) 0.0529(6) Uani 1 1 d . . . H11A H 0.5425 0.7598 0.3513 0.063 Uiso 1 1 calc R . . C12 C 0.5669(4) 0.9428(3) 0.2925(2) 0.0642(8) Uani 1 1 d . . . H12A H 0.4900 0.9190 0.2105 0.077 Uiso 1 1 calc R . . C13 C 0.6479(4) 1.0735(3) 0.3266(3) 0.0622(8) Uani 1 1 d . . . H13A H 0.6242 1.1342 0.2668 0.075 Uiso 1 1 calc R . . C14 C 0.7614(4) 1.1152(3) 0.4453(2) 0.0513(6) Uani 1 1 d . . . H14A H 0.8168 1.2025 0.4681 0.062 Uiso 1 1 calc R . . C15 C 0.7894(3) 1.0193(2) 0.5303(2) 0.0358(5) Uani 1 1 d . . . H1W H 0.738(4) 0.372(3) 0.997(3) 0.052(8) Uiso 1 1 d . . . H2W H 0.686(4) 0.398(3) 0.869(3) 0.064(9) Uiso 1 1 d . . . H3W H -0.062(4) 0.298(3) 0.775(3) 0.059(9) Uiso 1 1 d . . . H4W H 0.117(5) 0.288(3) 0.794(3) 0.063(10) Uiso 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 0.02119(15) 0.03118(17) 0.01546(15) 0.00271(11) 0.00447(11) 0.00480(12) N1 0.0277(8) 0.0322(9) 0.0222(8) 0.0036(6) 0.0076(6) 0.0036(6) N2 0.0438(10) 0.0343(9) 0.0417(10) 0.0055(8) 0.0188(9) 0.0114(8) N3 0.0321(9) 0.0294(8) 0.0265(8) 0.0032(7) 0.0125(7) 0.0045(7) N4 0.0401(10) 0.0258(8) 0.0335(9) 0.0024(7) 0.0126(8) 0.0000(7) N5 0.0405(10) 0.0248(8) 0.0338(9) 0.0018(7) 0.0126(8) -0.0009(7) O1 0.0255(7) 0.0372(7) 0.0160(6) 0.0017(5) 0.0008(5) 0.0104(6) O2 0.0456(9) 0.0493(9) 0.0199(7) -0.0037(6) 0.0014(6) 0.0239(7) O3 0.0459(8) 0.0395(8) 0.0331(8) 0.0149(6) 0.0259(7) 0.0152(7) O4 0.0239(6) 0.0303(7) 0.0328(7) 0.0008(6) 0.0123(5) 0.0056(5) O5 0.0303(7) 0.0483(9) 0.0193(7) 0.0052(6) 0.0098(6) 0.0134(6) O6 0.0442(11) 0.0289(8) 0.0607(12) -0.0018(8) -0.0023(9) 0.0052(8) C1 0.0206(8) 0.0280(9) 0.0148(8) 0.0026(7) 0.0039(6) 0.0020(7) C2 0.0201(8) 0.0258(9) 0.0147(8) 0.0037(6) 0.0037(6) 0.0042(7) C3 0.0202(8) 0.0247(8) 0.0164(8) 0.0032(6) 0.0063(6) 0.0040(6) C4 0.0168(8) 0.0310(9) 0.0173(8) 0.0036(7) 0.0028(6) 0.0053(7) C5 0.0207(8) 0.0269(9) 0.0194(8) -0.0012(7) 0.0066(7) -0.0004(7) C6 0.0304(10) 0.0288(9) 0.0211(9) 0.0021(7) 0.0070(7) 0.0038(8) C7 0.0376(11) 0.0410(12) 0.0363(11) 0.0055(9) 0.0183(9) 0.0111(9) C8 0.0299(10) 0.0343(10) 0.0323(11) 0.0062(8) 0.0113(8) 0.0014(8) C9 0.0311(10) 0.0272(9) 0.0324(10) 0.0032(8) 0.0156(8) 0.0022(8) C10 0.0376(11) 0.0384(11) 0.0307(10) 0.0047(9) 0.0125(9) 0.0031(9) C11 0.0542(15) 0.0580(16) 0.0387(13) -0.0028(11) 0.0101(11) -0.0006(12) C12 0.0605(17) 0.090(2) 0.0343(14) 0.0112(14) 0.0043(12) 0.0112(16) C13 0.0642(18) 0.076(2) 0.0456(15) 0.0287(14) 0.0125(13) 0.0188(15) C14 0.0591(16) 0.0466(14) 0.0501(15) 0.0198(12) 0.0176(12) 0.0129(12) C15 0.0378(11) 0.0363(11) 0.0340(11) 0.0075(9) 0.0124(9) 0.0065(9) 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_ _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 O5 Zn1 O5 180.000(1) . 2_667 O5 Zn1 O1 92.20(6) . 2_667 O5 Zn1 O1 87.80(6) 2_667 2_667 O5 Zn1 O1 87.80(6) . . O5 Zn1 O1 92.20(6) 2_667 . O1 Zn1 O1 180.000(1) 2_667 . O5 Zn1 N1 86.18(6) . 2_667 O5 Zn1 N1 93.82(6) 2_667 2_667 O1 Zn1 N1 90.48(7) 2_667 2_667 O1 Zn1 N1 89.52(7) . 2_667 O5 Zn1 N1 93.82(6) . . O5 Zn1 N1 86.18(6) 2_667 . O1 Zn1 N1 89.52(7) 2_667 . O1 Zn1 N1 90.48(7) . . N1 Zn1 N1 180.000(1) 2_667 . C6 N1 C7 103.00(16) . . C6 N1 Zn1 128.22(13) . . C7 N1 Zn1 128.73(13) . . C7 N2 N3 101.80(17) . . C6 N3 N2 110.20(16) . . C6 N3 C8 128.25(17) . . N2 N3 C8 121.40(16) . . C9 N4 C15 108.50(17) . . C9 N4 H4B 125.7 . . C15 N4 H4B 125.7 . . C9 N5 C10 108.39(17) . . C9 N5 H5A 125.8 . . C10 N5 H5A 125.8 . . C1 O1 Zn1 128.71(12) . . Zn1 O5 H1W 104.8(18) . . Zn1 O5 H2W 122.4(19) . . H1W O5 H2W 114(3) . . H3W O6 H4W 109(3) . . O2 C1 O1 126.00(16) . . O2 C1 C2 117.89(16) . . O1 C1 C2 116.11(15) . . C4 C2 C3 119.61(15) 2_566 . C4 C2 C1 119.20(15) 2_566 . C3 C2 C1 121.12(15) . . C4 C3 C2 119.95(15) . . C4 C3 C5 118.34(15) . . C2 C3 C5 121.56(15) . . C2 C4 C3 120.43(16) 2_566 . C2 C4 H4A 119.8 2_566 . C3 C4 H4A 119.8 . . O4 C5 O3 124.79(16) . . O4 C5 C3 118.08(16) . . O3 C5 C3 117.11(16) . . N1 C6 N3 109.82(17) . . N1 C6 H6A 125.1 . . N3 C6 H6A 125.1 . . N2 C7 N1 115.18(18) . . N2 C7 H7A 122.4 . . N1 C7 H7A 122.4 . . N3 C8 C9 112.00(16) . . N3 C8 H8A 109.2 . . C9 C8 H8A 109.2 . . N3 C8 H8B 109.2 . . C9 C8 H8B 109.2 . . H8A C8 H8B 107.9 . . N5 C9 N4 110.11(18) . . N5 C9 C8 126.03(18) . . N4 C9 C8 123.82(18) . . C15 C10 C11 121.1(2) . . C15 C10 N5 106.57(18) . . C11 C10 N5 132.3(2) . . C12 C11 C10 116.2(3) . . C12 C11 H11A 121.9 . . C10 C11 H11A 121.9 . . C11 C12 C13 122.5(3) . . C11 C12 H12A 118.8 . . C13 C12 H12A 118.8 . . C14 C13 C12 121.8(3) . . C14 C13 H13A 119.1 . . C12 C13 H13A 119.1 . . C13 C14 C15 116.1(3) . . C13 C14 H14A 122.0 . . C15 C14 H14A 122.0 . . N4 C15 C10 106.43(18) . . N4 C15 C14 131.2(2) . . C10 C15 C14 122.3(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Zn1 O5 2.1008(15) . Zn1 O5 2.1008(15) 2_667 Zn1 O1 2.1087(14) 2_667 Zn1 O1 2.1087(14) . Zn1 N1 2.1520(17) 2_667 Zn1 N1 2.1520(17) . N1 C6 1.317(2) . N1 C7 1.356(3) . N2 C7 1.310(3) . N2 N3 1.363(2) . N3 C6 1.333(2) . N3 C8 1.453(2) . N4 C9 1.330(3) . N4 C15 1.382(3) . N4 H4B 0.8600 . N5 C9 1.321(3) . N5 C10 1.388(3) . N5 H5A 0.8600 . O1 C1 1.264(2) . O2 C1 1.243(2) . O3 C5 1.253(2) . O4 C5 1.251(2) . O5 H1W 0.82(3) . O5 H2W 0.86(3) . O6 H3W 0.86(3) . O6 H4W 0.78(3) . C1 C2 1.516(2) . C2 C4 1.387(2) 2_566 C2 C3 1.397(2) . C3 C4 1.393(2) . C3 C5 1.509(2) . C4 C2 1.387(2) 2_566 C4 H4A 0.9300 . C6 H6A 0.9300 . C7 H7A 0.9300 . C8 C9 1.491(3) . C8 H8A 0.9700 . C8 H8B 0.9700 . C10 C15 1.386(3) . C10 C11 1.387(3) . C11 C12 1.375(4) . C11 H11A 0.9300 . C12 C13 1.389(4) . C12 H12A 0.9300 . C13 C14 1.365(4) . C13 H13A 0.9300 . C14 C15 1.393(3) . C14 H14A 0.9300 . 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 O6 H3W O3 0.86(3) 1.84(3) 2.704(3) 176(3) . O6 H4W O1 0.78(3) 2.19(3) 2.890(3) 149(3) . O5 H1W O2 0.82(3) 1.92(3) 2.697(2) 156(3) 2_667 O5 H2W O3 0.86(3) 1.83(3) 2.684(2) 172(3) 1_655 N5 H5A O4 0.86 1.76 2.606(2) 167.0 1_655 N4 H4B O6 0.86 1.77 2.607(3) 163.1 1_665 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 O5 Zn1 N1 C6 0.10(16) . . . . O5 Zn1 N1 C6 -179.90(16) 2_667 . . . O1 Zn1 N1 C6 92.27(16) 2_667 . . . O1 Zn1 N1 C6 -87.73(16) . . . . N1 Zn1 N1 C6 -109(100) 2_667 . . . O5 Zn1 N1 C7 176.86(17) . . . . O5 Zn1 N1 C7 -3.14(17) 2_667 . . . O1 Zn1 N1 C7 -90.97(17) 2_667 . . . O1 Zn1 N1 C7 89.03(17) . . . . N1 Zn1 N1 C7 68(100) 2_667 . . . C7 N2 N3 C6 -0.2(2) . . . . C7 N2 N3 C8 175.69(18) . . . . O5 Zn1 O1 C1 -164.49(15) . . . . O5 Zn1 O1 C1 15.51(15) 2_667 . . . O1 Zn1 O1 C1 -61(100) 2_667 . . . N1 Zn1 O1 C1 109.31(15) 2_667 . . . N1 Zn1 O1 C1 -70.69(15) . . . . Zn1 O1 C1 O2 -8.9(3) . . . . Zn1 O1 C1 C2 170.49(11) . . . . O2 C1 C2 C4 133.53(19) . . . 2_566 O1 C1 C2 C4 -45.9(2) . . . 2_566 O2 C1 C2 C3 -43.3(2) . . . . O1 C1 C2 C3 137.27(17) . . . . C4 C2 C3 C4 -1.1(3) 2_566 . . . C1 C2 C3 C4 175.77(16) . . . . C4 C2 C3 C5 174.53(16) 2_566 . . . C1 C2 C3 C5 -8.6(3) . . . . C2 C3 C4 C2 1.1(3) . . . 2_566 C5 C3 C4 C2 -174.66(16) . . . 2_566 C4 C3 C5 O4 -59.3(2) . . . . C2 C3 C5 O4 125.10(19) . . . . C4 C3 C5 O3 119.34(19) . . . . C2 C3 C5 O3 -56.3(2) . . . . C7 N1 C6 N3 -0.7(2) . . . . Zn1 N1 C6 N3 176.76(12) . . . . N2 N3 C6 N1 0.5(2) . . . . C8 N3 C6 N1 -174.95(18) . . . . N3 N2 C7 N1 -0.3(2) . . . . C6 N1 C7 N2 0.6(2) . . . . Zn1 N1 C7 N2 -176.80(14) . . . . C6 N3 C8 C9 101.1(2) . . . . N2 N3 C8 C9 -73.9(2) . . . . C10 N5 C9 N4 -0.6(2) . . . . C10 N5 C9 C8 -178.13(18) . . . . C15 N4 C9 N5 0.5(2) . . . . C15 N4 C9 C8 178.12(18) . . . . N3 C8 C9 N5 -62.2(3) . . . . N3 C8 C9 N4 120.6(2) . . . . C9 N5 C10 C15 0.4(2) . . . . C9 N5 C10 C11 -178.7(2) . . . . C15 C10 C11 C12 -0.4(4) . . . . N5 C10 C11 C12 178.6(2) . . . . C10 C11 C12 C13 0.9(4) . . . . C11 C12 C13 C14 -0.3(5) . . . . C12 C13 C14 C15 -0.6(4) . . . . C9 N4 C15 C10 -0.2(2) . . . . C9 N4 C15 C14 179.4(2) . . . . C11 C10 C15 N4 179.1(2) . . . . N5 C10 C15 N4 -0.1(2) . . . . C11 C10 C15 C14 -0.6(4) . . . . N5 C10 C15 C14 -179.8(2) . . . . C13 C14 C15 N4 -178.6(2) . . . . C13 C14 C15 C10 1.1(4) . . . .