# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p1 _database_code_depnum_ccdc_archive 'CCDC 873497' #TrackingRef 'web_deposit_cif_file_0_haohongjun_1332846824.p1-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H38 N6 O10 Zn2' _chemical_formula_weight 809.43 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.232(3) _cell_length_b 10.8471(17) _cell_length_c 18.894(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.711(3) _cell_angle_gamma 90.00 _cell_volume 3539.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5915 _cell_measurement_theta_min 4.435 _cell_measurement_theta_max 56.990 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 1.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7643 _exptl_absorpt_correction_T_max 0.8710 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker SMART CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 18945 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6931 _reflns_number_gt 5958 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+12.5116P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6931 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_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 0.31637(2) 0.19518(4) 0.02802(2) 0.01246(14) Uani 1 1 d . . . Zn2 Zn 0.21126(2) 0.19397(4) 0.12507(2) 0.01193(14) Uani 1 1 d . . . C1 C 0.1080(2) 0.0714(4) 0.2011(3) 0.0233(9) Uani 1 1 d . . . H1A H 0.1146 -0.0076 0.1824 0.028 Uiso 1 1 calc R . . C2 C 0.0680(3) 0.0965(4) 0.2483(3) 0.0290(10) Uani 1 1 d . . . H2A H 0.0411 0.0386 0.2686 0.035 Uiso 1 1 calc R . . C3 C 0.1160(2) 0.2687(4) 0.2223(2) 0.0172(8) Uani 1 1 d . . . C4 C 0.1360(3) 0.4013(4) 0.2224(3) 0.0296(10) Uani 1 1 d . . . H4B H 0.1675 0.4144 0.1897 0.044 Uiso 1 1 calc R . . H4C H 0.1652 0.4271 0.2733 0.044 Uiso 1 1 calc R . . H4D H 0.0883 0.4500 0.2041 0.044 Uiso 1 1 calc R . . C5 C 0.0477(3) 0.2860(5) 0.3175(3) 0.0277(10) Uani 1 1 d . . . H5A H 0.0924 0.3309 0.3516 0.033 Uiso 1 1 calc R . . H5B H 0.0309 0.2241 0.3476 0.033 Uiso 1 1 calc R . . C6 C -0.0178(3) 0.3766(5) 0.2856(3) 0.0287(10) Uani 1 1 d . . . H6A H -0.0671 0.3308 0.2653 0.034 Uiso 1 1 calc R . . H6B H -0.0086 0.4226 0.2440 0.034 Uiso 1 1 calc R . . C7 C -0.0247(3) 0.4671(4) 0.3446(3) 0.0284(10) Uani 1 1 d . . . H7A H 0.0243 0.5140 0.3640 0.034 Uiso 1 1 calc R . . H7B H -0.0666 0.5266 0.3211 0.034 Uiso 1 1 calc R . . C8 C 0.0129(2) 0.3543(5) 0.4678(2) 0.0264(10) Uani 1 1 d . . . H8A H 0.0674 0.3526 0.4778 0.032 Uiso 1 1 calc R . . C9 C -0.0266(2) 0.3064(4) 0.5109(2) 0.0241(10) Uani 1 1 d . . . H9A H -0.0044 0.2644 0.5570 0.029 Uiso 1 1 calc R . . C10 C -0.1107(2) 0.3886(4) 0.4151(2) 0.0194(9) Uani 1 1 d . . . C11 C -0.1841(3) 0.4363(6) 0.3608(3) 0.0386(13) Uani 1 1 d . . . H11A H -0.2278 0.4133 0.3776 0.058 Uiso 1 1 calc R . . H11B H -0.1913 0.4004 0.3114 0.058 Uiso 1 1 calc R . . H11C H -0.1813 0.5262 0.3578 0.058 Uiso 1 1 calc R . . C12 C 0.1473(2) 0.2194(4) -0.0422(2) 0.0184(8) Uani 1 1 d . . . C13 C 0.0787(2) 0.2426(4) -0.1100(2) 0.0176(8) Uani 1 1 d . . . C14 C 0.0087(2) 0.2767(4) -0.1017(2) 0.0211(9) Uani 1 1 d . . . H14A H 0.0050 0.2877 -0.0531 0.025 Uiso 1 1 calc R . . C15 C -0.0558(2) 0.2950(4) -0.1638(2) 0.0224(9) Uani 1 1 d . . . H15A H -0.1039 0.3165 -0.1575 0.027 Uiso 1 1 calc R . . C16 C -0.0508(2) 0.2822(4) -0.2347(2) 0.0169(8) Uani 1 1 d . . . C17 C -0.1217(2) 0.3019(3) -0.3020(2) 0.0182(8) Uani 1 1 d . . . C18 C 0.0195(2) 0.2504(4) -0.2435(2) 0.0214(9) Uani 1 1 d . . . H18A H 0.0236 0.2423 -0.2922 0.026 Uiso 1 1 calc R . . C19 C 0.0834(2) 0.2307(4) -0.1814(2) 0.0226(9) Uani 1 1 d . . . H19A H 0.1313 0.2085 -0.1877 0.027 Uiso 1 1 calc R . . C20 C 0.2564(2) -0.0404(4) 0.0706(2) 0.0187(9) Uani 1 1 d . . . C21 C 0.2572(2) -0.1779(4) 0.0698(2) 0.0169(8) Uani 1 1 d . . . C22 C 0.2358(2) -0.2433(4) 0.1231(2) 0.0178(8) Uani 1 1 d . . . H22A H 0.2170 -0.2010 0.1578 0.021 Uiso 1 1 calc R . . C23 C 0.2419(2) -0.3701(4) 0.1256(2) 0.0179(8) Uani 1 1 d . . . H23A H 0.2279 -0.4148 0.1625 0.022 Uiso 1 1 calc R . . C24 C 0.2682(2) -0.4326(4) 0.0748(2) 0.0180(8) Uani 1 1 d . . . C25 C 0.2727(2) -0.5708(4) 0.0767(2) 0.0171(8) Uani 1 1 d . . . C26 C 0.2889(2) -0.3676(4) 0.0215(2) 0.0220(9) Uani 1 1 d . . . H26A H 0.3069 -0.4105 -0.0135 0.026 Uiso 1 1 calc R . . C27 C 0.2837(2) -0.2408(4) 0.0186(2) 0.0210(9) Uani 1 1 d . . . H27A H 0.2981 -0.1966 -0.0183 0.025 Uiso 1 1 calc R . . C28 C 0.3840(7) -0.5283(10) -0.1517(7) 0.133(5) Uani 1 1 d . . . H28A H 0.4249 -0.4679 -0.1487 0.199 Uiso 1 1 calc R . . H28B H 0.3768 -0.5812 -0.1954 0.199 Uiso 1 1 calc R . . H28C H 0.3989 -0.5790 -0.1063 0.199 Uiso 1 1 calc R . . C29 C 0.2441(5) -0.5368(7) -0.1637(4) 0.088(3) Uani 1 1 d . . . H29A H 0.2005 -0.4811 -0.1681 0.132 Uiso 1 1 calc R . . H29B H 0.2535 -0.5877 -0.1188 0.132 Uiso 1 1 calc R . . H29C H 0.2318 -0.5901 -0.2078 0.132 Uiso 1 1 calc R . . C30 C 0.3121(4) -0.3426(6) -0.1586(3) 0.0468(14) Uani 1 1 d . . . H30A H 0.2635 -0.3048 -0.1644 0.056 Uiso 1 1 calc R . . C31 C -0.1210(3) 0.1294(6) 0.1280(3) 0.0464(14) Uani 1 1 d . . . H31A H -0.1245 0.0422 0.1307 0.056 Uiso 1 1 calc R . . C32 C -0.0549(3) 0.0965(5) 0.0372(3) 0.0436(13) Uani 1 1 d . . . H32A H -0.0613 0.0100 0.0491 0.065 Uiso 1 1 calc R . . H32B H 0.0003 0.1144 0.0480 0.065 Uiso 1 1 calc R . . H32C H -0.0824 0.1115 -0.0158 0.065 Uiso 1 1 calc R . . C33 C -0.0803(4) 0.3063(5) 0.0725(3) 0.0478(15) Uani 1 1 d . . . H33A H -0.1058 0.3494 0.1038 0.072 Uiso 1 1 calc R . . H33B H -0.1058 0.3282 0.0200 0.072 Uiso 1 1 calc R . . H33C H -0.0257 0.3304 0.0874 0.072 Uiso 1 1 calc R . . N1 N 0.13785(19) 0.1817(3) 0.18471(19) 0.0178(7) Uani 1 1 d . . . N2 N 0.0733(2) 0.2213(3) 0.2615(2) 0.0231(8) Uani 1 1 d . . . N3 N -0.0411(2) 0.4060(3) 0.4069(2) 0.0227(8) Uani 1 1 d . . . N4 N -0.1041(2) 0.3284(3) 0.47712(19) 0.0180(7) Uani 1 1 d . . . N5 N 0.3130(4) -0.4649(5) -0.1582(3) 0.0575(14) Uani 1 1 d . . . N6 N -0.0859(2) 0.1745(4) 0.0818(3) 0.0376(10) Uani 1 1 d . . . O1 O 0.21078(18) 0.2049(4) -0.05210(18) 0.0368(9) Uani 1 1 d . . . O2 O 0.13529(17) 0.2155(3) 0.01860(16) 0.0260(7) Uani 1 1 d . . . O3 O -0.18493(17) 0.3145(3) -0.29077(17) 0.0265(7) Uani 1 1 d . . . O4 O -0.11130(18) 0.3034(3) -0.36389(16) 0.0296(8) Uani 1 1 d . . . O5 O 0.21758(17) 0.0114(3) 0.10533(17) 0.0230(7) Uani 1 1 d . . . O6 O 0.2971(2) 0.0124(3) 0.0375(2) 0.0330(8) Uani 1 1 d . . . O7 O 0.24031(19) -0.6265(3) 0.11587(19) 0.0275(7) Uani 1 1 d . . . O8 O 0.3076(2) -0.6212(3) 0.0372(2) 0.0363(9) Uani 1 1 d . . . O9 O 0.3663(3) -0.2731(5) -0.1524(3) 0.0729(14) Uani 1 1 d . . . O10 O -0.1490(3) 0.1894(4) 0.1671(3) 0.0604(12) 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 0.0126(2) 0.0113(2) 0.0137(2) -0.00074(16) 0.00457(18) 0.00133(16) Zn2 0.0123(2) 0.0107(2) 0.0129(2) -0.00030(16) 0.00413(18) 0.00066(16) C1 0.025(2) 0.016(2) 0.031(2) -0.0035(18) 0.0121(19) -0.0068(17) C2 0.027(2) 0.027(2) 0.037(3) 0.004(2) 0.017(2) -0.0065(19) C3 0.0161(19) 0.020(2) 0.017(2) 0.0012(16) 0.0075(16) 0.0027(16) C4 0.041(3) 0.020(2) 0.035(3) -0.0070(19) 0.022(2) -0.004(2) C5 0.024(2) 0.042(3) 0.020(2) -0.006(2) 0.0112(19) 0.000(2) C6 0.028(2) 0.039(3) 0.025(2) -0.002(2) 0.0160(19) 0.001(2) C7 0.034(2) 0.033(3) 0.030(2) -0.002(2) 0.026(2) -0.009(2) C8 0.016(2) 0.041(3) 0.025(2) -0.005(2) 0.0103(18) -0.0005(19) C9 0.021(2) 0.036(3) 0.014(2) -0.0028(18) 0.0059(17) 0.0087(18) C10 0.022(2) 0.022(2) 0.018(2) -0.0014(16) 0.0121(17) -0.0030(17) C11 0.029(2) 0.059(4) 0.033(3) 0.019(3) 0.017(2) 0.008(2) C12 0.017(2) 0.015(2) 0.018(2) 0.0008(16) -0.0009(16) 0.0019(15) C13 0.0153(19) 0.019(2) 0.018(2) 0.0039(16) 0.0045(16) 0.0033(16) C14 0.020(2) 0.029(2) 0.013(2) 0.0009(17) 0.0041(16) 0.0012(17) C15 0.016(2) 0.029(2) 0.023(2) 0.0021(18) 0.0064(17) 0.0042(17) C16 0.0161(19) 0.017(2) 0.016(2) 0.0034(15) 0.0017(16) -0.0005(15) C17 0.021(2) 0.0122(19) 0.018(2) 0.0011(15) 0.0022(17) 0.0008(15) C18 0.019(2) 0.029(2) 0.016(2) -0.0004(17) 0.0057(16) 0.0025(18) C19 0.017(2) 0.030(2) 0.019(2) 0.0015(18) 0.0052(17) 0.0042(18) C20 0.0168(19) 0.015(2) 0.020(2) -0.0012(16) -0.0002(16) -0.0037(15) C21 0.0154(19) 0.0121(19) 0.022(2) 0.0010(15) 0.0038(16) 0.0019(15) C22 0.0192(19) 0.019(2) 0.019(2) -0.0047(16) 0.0112(16) 0.0014(16) C23 0.0162(19) 0.016(2) 0.023(2) 0.0019(16) 0.0084(16) 0.0000(16) C24 0.0151(18) 0.017(2) 0.021(2) -0.0021(16) 0.0057(16) -0.0020(15) C25 0.0169(19) 0.018(2) 0.016(2) 0.0000(16) 0.0049(16) 0.0009(16) C26 0.025(2) 0.018(2) 0.025(2) -0.0033(17) 0.0105(18) 0.0022(17) C27 0.023(2) 0.017(2) 0.023(2) -0.0005(17) 0.0078(17) -0.0012(17) C28 0.150(10) 0.105(9) 0.176(12) 0.029(8) 0.100(10) 0.056(8) C29 0.137(8) 0.073(5) 0.041(4) 0.008(4) 0.010(4) -0.054(5) C30 0.051(3) 0.062(4) 0.034(3) -0.004(3) 0.023(3) -0.007(3) C31 0.039(3) 0.053(4) 0.045(3) -0.002(3) 0.011(3) -0.001(3) C32 0.039(3) 0.043(3) 0.049(3) -0.007(3) 0.013(3) -0.004(2) C33 0.054(4) 0.042(3) 0.042(3) -0.001(3) 0.007(3) -0.006(3) N1 0.0168(16) 0.0200(18) 0.0192(18) -0.0021(14) 0.0094(14) 0.0000(13) N2 0.0220(18) 0.028(2) 0.0213(19) 0.0006(15) 0.0092(15) 0.0002(15) N3 0.0231(18) 0.029(2) 0.0221(19) -0.0050(15) 0.0160(15) -0.0047(15) N4 0.0183(17) 0.0196(18) 0.0200(18) -0.0007(14) 0.0114(14) -0.0011(14) N5 0.083(4) 0.055(3) 0.040(3) 0.004(2) 0.027(3) 0.007(3) N6 0.032(2) 0.035(2) 0.041(3) -0.0008(19) 0.005(2) -0.0009(18) O1 0.0150(15) 0.070(3) 0.0211(17) 0.0032(16) -0.0007(13) 0.0111(15) O2 0.0218(15) 0.0399(19) 0.0133(15) 0.0049(13) 0.0016(12) 0.0028(13) O3 0.0154(14) 0.0384(19) 0.0210(16) -0.0071(13) -0.0008(12) 0.0053(13) O4 0.0209(15) 0.053(2) 0.0112(15) 0.0098(14) -0.0002(12) -0.0026(14) O5 0.0265(15) 0.0132(14) 0.0334(17) -0.0053(12) 0.0154(14) 0.0021(12) O6 0.046(2) 0.0171(16) 0.046(2) 0.0000(14) 0.0293(17) -0.0080(14) O7 0.0374(18) 0.0109(14) 0.0419(19) 0.0013(13) 0.0237(15) 0.0005(13) O8 0.066(2) 0.0084(15) 0.050(2) 0.0029(14) 0.040(2) 0.0010(15) O9 0.071(3) 0.080(4) 0.078(4) -0.007(3) 0.040(3) -0.025(3) O10 0.057(3) 0.074(3) 0.054(3) -0.010(2) 0.023(2) -0.006(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 N4 1.997(3) 4_665 ? Zn1 O8 2.011(3) 1_565 ? Zn1 O6 2.032(3) . ? Zn1 O1 2.034(3) . ? Zn1 O4 2.045(3) 4_666 ? Zn1 Zn2 3.0477(7) . ? Zn2 N1 2.012(3) . ? Zn2 O5 2.025(3) . ? Zn2 O7 2.040(3) 1_565 ? Zn2 O3 2.046(3) 4_666 ? Zn2 O2 2.057(3) . ? C1 C2 1.348(6) . ? C1 N1 1.389(5) . ? C1 H1A 0.9500 . ? C2 N2 1.374(6) . ? C2 H2A 0.9500 . ? C3 N1 1.318(5) . ? C3 N2 1.338(5) . ? C3 C4 1.484(6) . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 H4D 0.9800 . ? C5 N2 1.465(5) . ? C5 C6 1.514(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.464(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.352(6) . ? C8 N3 1.371(6) . ? C8 H8A 0.9500 . ? C9 N4 1.372(5) . ? C9 H9A 0.9500 . ? C10 N4 1.312(5) . ? C10 N3 1.341(5) . ? C10 C11 1.493(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O2 1.237(5) . ? C12 O1 1.240(5) . ? C12 C13 1.497(5) . ? C13 C19 1.384(6) . ? C13 C14 1.385(6) . ? C14 C15 1.384(6) . ? C14 H14A 0.9500 . ? C15 C16 1.379(6) . ? C15 H15A 0.9500 . ? C16 C18 1.389(6) . ? C16 C17 1.509(5) . ? C17 O4 1.243(5) . ? C17 O3 1.245(5) . ? C18 C19 1.379(6) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 O5 1.244(5) . ? C20 O6 1.252(5) . ? C20 C21 1.491(6) . ? C21 C22 1.388(6) . ? C21 C27 1.391(6) . ? C22 C23 1.379(6) . ? C22 H22A 0.9500 . ? C23 C24 1.380(6) . ? C23 H23A 0.9500 . ? C24 C26 1.377(6) . ? C24 C25 1.501(6) . ? C25 O7 1.242(5) . ? C25 O8 1.250(5) . ? C26 C27 1.378(6) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 N5 1.436(11) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 N5 1.454(9) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O9 1.218(7) . ? C30 N5 1.327(8) . ? C30 H30A 0.9500 . ? C31 O10 1.213(7) . ? C31 N6 1.332(7) . ? C31 H31A 0.9500 . ? C32 N6 1.431(7) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 N6 1.447(7) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N4 Zn1 1.997(3) 4_566 ? O3 Zn2 2.046(3) 4_565 ? O4 Zn1 2.045(3) 4_565 ? O7 Zn2 2.040(3) 1_545 ? O8 Zn1 2.011(3) 1_545 ? 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 N4 Zn1 O8 105.01(14) 4_665 1_565 ? N4 Zn1 O6 95.16(14) 4_665 . ? O8 Zn1 O6 159.83(14) 1_565 . ? N4 Zn1 O1 107.95(14) 4_665 . ? O8 Zn1 O1 86.00(16) 1_565 . ? O6 Zn1 O1 88.11(15) . . ? N4 Zn1 O4 98.43(14) 4_665 4_666 ? O8 Zn1 O4 87.14(15) 1_565 4_666 ? O6 Zn1 O4 89.65(14) . 4_666 ? O1 Zn1 O4 153.61(14) . 4_666 ? N4 Zn1 Zn2 169.42(10) 4_665 . ? O8 Zn1 Zn2 82.49(10) 1_565 . ? O6 Zn1 Zn2 77.47(9) . . ? O1 Zn1 Zn2 79.66(10) . . ? O4 Zn1 Zn2 74.20(9) 4_666 . ? N1 Zn2 O5 97.22(13) . . ? N1 Zn2 O7 110.40(13) . 1_565 ? O5 Zn2 O7 152.38(13) . 1_565 ? N1 Zn2 O3 100.22(13) . 4_666 ? O5 Zn2 O3 90.37(13) . 4_666 ? O7 Zn2 O3 84.73(13) 1_565 4_666 ? N1 Zn2 O2 101.25(13) . . ? O5 Zn2 O2 89.49(13) . . ? O7 Zn2 O2 85.42(13) 1_565 . ? O3 Zn2 O2 158.38(13) 4_666 . ? N1 Zn2 Zn1 175.58(10) . . ? O5 Zn2 Zn1 79.02(9) . . ? O7 Zn2 Zn1 73.39(9) 1_565 . ? O3 Zn2 Zn1 82.21(9) 4_666 . ? O2 Zn2 Zn1 76.54(9) . . ? C2 C1 N1 107.9(4) . . ? C2 C1 H1A 126.0 . . ? N1 C1 H1A 126.0 . . ? C1 C2 N2 107.3(4) . . ? C1 C2 H2A 126.3 . . ? N2 C2 H2A 126.3 . . ? N1 C3 N2 110.7(4) . . ? N1 C3 C4 125.3(4) . . ? N2 C3 C4 124.0(4) . . ? C3 C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4B C4 H4D 109.5 . . ? H4C C4 H4D 109.5 . . ? N2 C5 C6 114.6(4) . . ? N2 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? N2 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C5 C6 C7 111.6(4) . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N3 C7 C6 112.5(4) . . ? N3 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? N3 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 N3 106.6(4) . . ? C9 C8 H8A 126.7 . . ? N3 C8 H8A 126.7 . . ? C8 C9 N4 108.7(4) . . ? C8 C9 H9A 125.7 . . ? N4 C9 H9A 125.7 . . ? N4 C10 N3 110.7(4) . . ? N4 C10 C11 126.2(4) . . ? N3 C10 C11 123.0(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O1 126.0(4) . . ? O2 C12 C13 116.9(4) . . ? O1 C12 C13 117.1(4) . . ? C19 C13 C14 118.8(4) . . ? C19 C13 C12 121.6(4) . . ? C14 C13 C12 119.6(4) . . ? C15 C14 C13 120.4(4) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C16 C15 C14 120.4(4) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C15 C16 C18 119.5(4) . . ? C15 C16 C17 119.9(4) . . ? C18 C16 C17 120.5(4) . . ? O4 C17 O3 126.0(4) . . ? O4 C17 C16 116.5(4) . . ? O3 C17 C16 117.5(4) . . ? C19 C18 C16 119.7(4) . . ? C19 C18 H18A 120.1 . . ? C16 C18 H18A 120.1 . . ? C18 C19 C13 121.1(4) . . ? C18 C19 H19A 119.5 . . ? C13 C19 H19A 119.5 . . ? O5 C20 O6 125.9(4) . . ? O5 C20 C21 117.8(4) . . ? O6 C20 C21 116.3(4) . . ? C22 C21 C27 119.7(4) . . ? C22 C21 C20 119.9(4) . . ? C27 C21 C20 120.3(4) . . ? C23 C22 C21 119.7(4) . . ? C23 C22 H22A 120.1 . . ? C21 C22 H22A 120.1 . . ? C22 C23 C24 120.6(4) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C26 C24 C23 119.6(4) . . ? C26 C24 C25 120.2(4) . . ? C23 C24 C25 120.2(4) . . ? O7 C25 O8 125.0(4) . . ? O7 C25 C24 117.8(4) . . ? O8 C25 C24 117.2(4) . . ? C24 C26 C27 120.7(4) . . ? C24 C26 H26A 119.7 . . ? C27 C26 H26A 119.7 . . ? C26 C27 C21 119.7(4) . . ? C26 C27 H27A 120.1 . . ? C21 C27 H27A 120.1 . . ? N5 C28 H28A 109.5 . . ? N5 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N5 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N5 C29 H29A 109.5 . . ? N5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O9 C30 N5 127.6(7) . . ? O9 C30 H30A 116.2 . . ? N5 C30 H30A 116.2 . . ? O10 C31 N6 125.9(6) . . ? O10 C31 H31A 117.0 . . ? N6 C31 H31A 117.0 . . ? N6 C32 H32A 109.5 . . ? N6 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N6 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N6 C33 H33A 109.5 . . ? N6 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N6 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C3 N1 C1 106.8(3) . . ? C3 N1 Zn2 128.7(3) . . ? C1 N1 Zn2 124.1(3) . . ? C3 N2 C2 107.3(4) . . ? C3 N2 C5 126.3(4) . . ? C2 N2 C5 125.7(4) . . ? C10 N3 C8 107.3(3) . . ? C10 N3 C7 127.0(4) . . ? C8 N3 C7 125.7(4) . . ? C10 N4 C9 106.7(4) . . ? C10 N4 Zn1 128.4(3) . 4_566 ? C9 N4 Zn1 123.5(3) . 4_566 ? C30 N5 C28 119.2(7) . . ? C30 N5 C29 121.8(7) . . ? C28 N5 C29 119.0(8) . . ? C31 N6 C32 122.1(5) . . ? C31 N6 C33 120.6(5) . . ? C32 N6 C33 117.2(5) . . ? C12 O1 Zn1 126.9(3) . . ? C12 O2 Zn2 130.4(3) . . ? C17 O3 Zn2 122.6(3) . 4_565 ? C17 O4 Zn1 134.0(3) . 4_565 ? C20 O5 Zn2 128.0(3) . . ? C20 O6 Zn1 129.6(3) . . ? C25 O7 Zn2 134.5(3) . 1_545 ? C25 O8 Zn1 123.7(3) . 1_545 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.925 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.107 data_p2 _database_code_depnum_ccdc_archive 'CCDC 873498' #TrackingRef 'web_deposit_cif_file_0_haohongjun_1332846824.p1-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 N4 O7 Zn' _chemical_formula_weight 486.80 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 P21/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 9.695(2) _cell_length_b 18.427(4) _cell_length_c 12.520(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.434(4) _cell_angle_gamma 90.00 _cell_volume 2145.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2531 _cell_measurement_theta_min 4.907 _cell_measurement_theta_max 46.591 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8900 _exptl_absorpt_correction_T_max 0.8900 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker SMART CCD' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 10746 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3774 _reflns_number_gt 3049 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+1.6772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3774 _refine_ls_number_parameters 334 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.020 _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 0.93513(5) 0.14233(3) 0.87517(4) 0.0273(2) Uani 1 1 d . . . C1 C 0.9047(5) 0.2824(2) 0.7462(4) 0.0358(10) Uani 1 1 d . . . H1A H 0.9637 0.2659 0.7021 0.043 Uiso 1 1 calc R . . C2 C 0.8318(5) 0.3451(2) 0.7326(4) 0.0348(10) Uani 1 1 d . . . H2A H 0.8295 0.3810 0.6777 0.042 Uiso 1 1 calc R . . C3 C 0.7932(4) 0.2871(2) 0.8739(3) 0.0291(9) Uani 1 1 d . . . C4 C 0.7392(6) 0.2711(3) 0.9705(4) 0.0459(12) Uani 1 1 d . . . H4A H 0.7771 0.2241 1.0025 0.069 Uiso 1 1 calc R . . H4B H 0.6339 0.2692 0.9463 0.069 Uiso 1 1 calc R . . H4C H 0.7709 0.3092 1.0267 0.069 Uiso 1 1 calc R . . C5 C 0.6642(5) 0.4060(2) 0.8266(4) 0.0354(10) Uani 1 1 d . . . H5A H 0.7125 0.4534 0.8278 0.042 Uiso 1 1 calc R . . H5B H 0.6421 0.3999 0.8986 0.042 Uiso 1 1 calc R . . C6 C 0.5258(5) 0.4052(3) 0.7329(4) 0.0443(12) Uani 1 1 d . . . H6A H 0.4677 0.4478 0.7414 0.053 Uiso 1 1 calc R . . H6B H 0.5499 0.4109 0.6615 0.053 Uiso 1 1 calc R . . C7 C 0.4348(5) 0.3380(3) 0.7255(4) 0.0463(12) Uani 1 1 d . . . H7C H 0.4274 0.3242 0.7976 0.056 Uiso 0.50 1 d PR . . H7D H 0.4716 0.2980 0.6928 0.056 Uiso 0.50 1 d PR . . H7A H 0.3850 0.3419 0.7815 0.056 Uiso 0.50 1 d PR . . H7B H 0.4986 0.2972 0.7448 0.056 Uiso 0.50 1 d PR . . C8 C 0.2077(11) 0.4140(6) 0.6794(9) 0.036(2) Uani 0.50 1 d PU . . H8A H 0.2319 0.4418 0.7471 0.043 Uiso 0.50 1 d PR . . H11C H 0.2084 0.4472 0.6671 0.054 Uiso 0.50 1 d PR . . C8' C 0.3440(14) 0.2780(7) 0.5316(11) 0.049(3) Uani 0.50 1 d PU . . H8B H 0.4029 0.2480 0.5402 0.059 Uiso 0.50 1 d PR . . C9 C 0.0879(10) 0.4209(5) 0.5945(8) 0.027(2) Uani 0.50 1 d PU . . H9A H 0.0281 0.4489 0.5859 0.032 Uiso 0.50 1 d PR . . C9' C 0.2321(13) 0.2878(6) 0.4473(11) 0.040(3) Uani 0.50 1 d PU . . H9B H 0.2180 0.2683 0.3739 0.048 Uiso 0.50 1 d PR . . H11E H 0.2172 0.2455 0.4745 0.060 Uiso 0.50 1 d PR . . H11F H 0.2831 0.3059 0.4157 0.060 Uiso 0.50 1 d PR . . C10 C 0.2261(12) 0.3402(6) 0.5483(10) 0.026(3) Uani 0.50 1 d PU . . C10' C 0.2002(14) 0.3550(7) 0.5783(11) 0.034(3) Uani 0.50 1 d PU . . C11 C 0.2840(17) 0.2853(8) 0.4859(13) 0.044(3) Uani 0.50 1 d PU . . C11' C 0.1395(15) 0.4090(7) 0.6454(12) 0.040(3) Uani 0.50 1 d PU . . H11B H 0.1321 0.3849 0.7116 0.060 Uiso 0.50 1 d PR . . C12 C 0.6721(5) 0.0927(2) 0.9016(4) 0.0384(11) Uani 1 1 d . . . C13 C 0.5835(5) 0.0451(2) 0.9539(4) 0.0350(10) Uani 1 1 d . . . C14 C 0.6465(5) -0.0071(2) 1.0304(4) 0.0377(11) Uani 1 1 d . . . H14A H 0.7481 -0.0126 1.0513 0.045 Uiso 1 1 calc R . . C15 C 0.4346(5) 0.0519(2) 0.9225(4) 0.0392(11) Uani 1 1 d . . . H15A H 0.3888 0.0872 0.8688 0.047 Uiso 1 1 calc R . . C16 C 1.0066(4) 0.0452(2) 0.5917(3) 0.0294(9) Uani 1 1 d . . . C17 C 1.0139(4) 0.0939(2) 0.6891(4) 0.0327(10) Uani 1 1 d . . . C18 C 0.9548(4) -0.0256(2) 0.5879(4) 0.0329(10) Uani 1 1 d . . . H18A H 0.9230 -0.0435 0.6480 0.040 Uiso 1 1 calc R . . C19 C 1.0510(5) 0.0702(2) 0.5022(4) 0.0336(10) Uani 1 1 d . . . H19A H 1.0857 0.1184 0.5027 0.040 Uiso 1 1 calc R . . N1 N 0.8798(4) 0.24559(19) 0.8354(3) 0.0313(8) Uani 1 1 d . . . N2 N 0.7614(4) 0.34742(18) 0.8128(3) 0.0291(8) Uani 1 1 d . . . N3 N 0.2921(8) 0.3647(4) 0.6514(6) 0.0329(17) Uani 0.50 1 d P . . N3' N 0.3277(9) 0.3221(5) 0.6200(7) 0.0409(19) Uani 0.50 1 d P . . N4 N 0.0966(7) 0.3736(4) 0.5139(6) 0.0200(15) Uani 0.50 1 d P . . N4' N 0.1353(9) 0.3381(5) 0.4785(8) 0.041(2) Uani 0.50 1 d P . . O1 O 0.8076(3) 0.09185(17) 0.9474(3) 0.0417(8) Uani 1 1 d . . . O1W O 0.3497(5) 0.5337(3) 0.8876(5) 0.115(2) Uani 1 1 d . . . H1WA H 0.3591 0.4905 0.9100 0.138 Uiso 1 1 d R . . H1WB H 0.2647 0.5414 0.8487 0.138 Uiso 1 1 d R . . O2 O 0.6145(4) 0.1297(2) 0.8202(3) 0.0693(13) Uani 1 1 d . . . O2W O 0.3586(5) 0.1461(3) 0.6623(4) 0.114(2) Uani 1 1 d . . . H2WA H 0.4261 0.1348 0.7106 0.137 Uiso 1 1 d R . . H2WB H 0.2779 0.1393 0.6781 0.137 Uiso 1 1 d R . . O3 O 1.0961(4) 0.14596(18) 0.7077(3) 0.0514(9) Uani 1 1 d . . . O3W O 0.4140(5) 0.3961(3) 0.9732(4) 0.0860(14) Uani 1 1 d . . . H3WA H 0.4893 0.4204 1.0040 0.103 Uiso 1 1 d R . . H3WB H 0.3818 0.3788 1.0244 0.103 Uiso 1 1 d R . . O4 O 0.9309(3) 0.07864(18) 0.7485(3) 0.0404(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0227(3) 0.0344(3) 0.0245(3) -0.0006(2) 0.0060(2) 0.0007(2) C1 0.034(2) 0.042(3) 0.035(3) 0.001(2) 0.015(2) -0.003(2) C2 0.038(2) 0.037(3) 0.032(2) 0.0043(19) 0.013(2) -0.003(2) C3 0.024(2) 0.038(2) 0.024(2) 0.0015(18) 0.0045(17) -0.0030(18) C4 0.059(3) 0.045(3) 0.038(3) 0.006(2) 0.021(2) 0.009(2) C5 0.034(2) 0.036(2) 0.035(3) -0.001(2) 0.0087(19) 0.003(2) C6 0.035(3) 0.049(3) 0.049(3) 0.008(2) 0.012(2) 0.011(2) C7 0.028(2) 0.068(3) 0.038(3) 0.005(2) 0.002(2) -0.001(2) C8 0.031(4) 0.044(4) 0.034(4) -0.007(3) 0.011(3) 0.001(4) C8' 0.048(5) 0.050(5) 0.046(5) -0.009(4) 0.009(4) 0.008(4) C9 0.024(4) 0.034(4) 0.021(4) 0.000(3) 0.003(3) 0.001(3) C9' 0.038(5) 0.039(4) 0.047(5) -0.006(4) 0.018(4) 0.004(4) C10 0.025(4) 0.030(4) 0.023(4) 0.003(3) 0.007(4) 0.001(3) C10' 0.034(5) 0.035(5) 0.034(5) 0.002(4) 0.014(4) -0.005(4) C11 0.045(5) 0.042(5) 0.041(5) -0.006(4) 0.007(4) 0.006(4) C11' 0.041(5) 0.043(4) 0.040(5) -0.003(4) 0.019(4) 0.004(4) C12 0.051(3) 0.039(3) 0.033(3) -0.007(2) 0.024(2) -0.010(2) C13 0.043(3) 0.036(2) 0.033(3) -0.006(2) 0.023(2) -0.003(2) C14 0.044(3) 0.043(3) 0.034(3) -0.006(2) 0.024(2) 0.001(2) C15 0.052(3) 0.037(2) 0.034(3) -0.001(2) 0.021(2) 0.001(2) C16 0.025(2) 0.035(2) 0.028(2) -0.0025(18) 0.0063(17) 0.0023(18) C17 0.027(2) 0.038(2) 0.031(2) -0.0024(19) 0.0058(18) -0.0003(19) C18 0.029(2) 0.040(2) 0.030(2) 0.005(2) 0.0098(19) 0.0025(19) C19 0.032(2) 0.035(2) 0.034(2) -0.002(2) 0.0094(19) -0.0033(19) N1 0.0279(19) 0.0354(19) 0.031(2) 0.0018(16) 0.0084(15) 0.0007(16) N2 0.0240(18) 0.0315(19) 0.029(2) -0.0044(15) 0.0025(15) -0.0033(14) N3 0.025(4) 0.038(5) 0.030(4) -0.005(4) -0.002(4) 0.007(3) N3' 0.034(5) 0.049(5) 0.035(5) 0.009(4) 0.002(4) 0.003(4) N4 0.014(4) 0.029(4) 0.016(4) -0.002(3) 0.003(3) 0.004(3) N4' 0.020(4) 0.055(6) 0.039(5) 0.012(4) -0.004(4) -0.005(4) O1 0.0416(19) 0.0417(18) 0.051(2) 0.0087(15) 0.0273(16) 0.0010(15) O1W 0.056(3) 0.152(5) 0.123(4) 0.079(4) 0.002(3) -0.001(3) O2 0.056(2) 0.096(3) 0.048(2) 0.026(2) 0.0030(19) -0.035(2) O2W 0.053(3) 0.245(8) 0.042(3) 0.032(3) 0.012(2) 0.000(3) O3 0.056(2) 0.053(2) 0.054(2) -0.0219(17) 0.0297(18) -0.0174(17) O3W 0.083(3) 0.102(4) 0.088(4) -0.007(3) 0.048(3) -0.009(3) O4 0.0401(18) 0.0502(19) 0.0364(18) -0.0114(15) 0.0198(15) -0.0046(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.961(3) . ? Zn1 O4 1.964(3) . ? Zn1 N1 2.001(4) . ? Zn1 N4 2.004(7) 4_666 ? Zn1 N4' 2.037(8) 4_666 ? C1 C2 1.341(6) . ? C1 N1 1.385(6) . ? C1 H1A 0.9500 . ? C2 N2 1.366(6) . ? C2 H2A 0.9500 . ? C3 N1 1.324(5) . ? C3 N2 1.335(5) . ? C3 C4 1.476(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N2 1.474(5) . ? C5 C6 1.512(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.508(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3' 1.460(9) . ? C7 N3 1.514(9) . ? C7 H7C 0.9599 . ? C7 H7D 0.9600 . ? C7 H7A 0.9598 . ? C7 H7B 0.9601 . ? C8 C11' 0.685(13) . ? C8 N3 1.334(13) . ? C8 C9 1.340(13) . ? C8 C10' 1.655(17) . ? C8 H8A 0.9599 . ? C8 H11C 0.6302 . ? C8 H11B 1.0742 . ? C8' C11 0.704(13) . ? C8' C9' 1.294(16) . ? C8' N3' 1.417(15) . ? C8' C10 1.672(17) . ? C8' H8B 0.7804 . ? C9 C11' 0.724(12) . ? C9 N4 1.354(11) . ? C9 C10' 1.682(16) . ? C9 H9A 0.7603 . ? C9' C11 0.592(15) . ? C9' N4' 1.449(15) . ? C9' C10 1.604(17) . ? C9' H9B 0.9601 . ? C9' H11E 0.8800 . ? C9' H11F 0.7895 . ? C10 C10' 0.576(12) . ? C10 N4' 1.051(13) . ? C10 N3' 1.177(13) . ? C10 N3 1.346(14) . ? C10 N4 1.355(13) . ? C10 C11 1.482(18) . ? C10' N3 1.096(14) . ? C10' N4 1.148(14) . ? C10' N4' 1.268(16) . ? C10' N3' 1.342(15) . ? C10' C11' 1.524(17) . ? C11 N4' 1.719(18) . ? C11 N3' 1.748(17) . ? C11 H11E 0.9627 . ? C11 H11F 0.9555 . ? C11' N3 1.672(15) . ? C11' N4 1.709(15) . ? C11' H11C 0.9553 . ? C11' H11B 0.9602 . ? C12 O2 1.222(6) . ? C12 O1 1.275(6) . ? C12 C13 1.501(6) . ? C13 C14 1.373(6) . ? C13 C15 1.390(7) . ? C14 C15 1.382(6) 3_657 ? C14 H14A 0.9500 . ? C15 C14 1.382(6) 3_657 ? C15 H15A 0.9500 . ? C16 C19 1.388(6) . ? C16 C18 1.395(6) . ? C16 C17 1.499(6) . ? C17 O3 1.227(5) . ? C17 O4 1.272(5) . ? C18 C19 1.383(6) 3_756 ? C18 H18A 0.9500 . ? C19 C18 1.383(6) 3_756 ? C19 H19A 0.9500 . ? N3 N3' 0.983(10) . ? N4 N4' 0.927(10) . ? N4 Zn1 2.004(7) 4_465 ? N4' Zn1 2.037(8) 4_465 ? O1W H1WA 0.8395 . ? O1W H1WB 0.8421 . ? O2W H2WA 0.7844 . ? O2W H2WB 0.8683 . ? O3W H3WA 0.8501 . ? O3W H3WB 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 102.53(14) . . ? O1 Zn1 N1 113.96(14) . . ? O4 Zn1 N1 115.10(14) . . ? O1 Zn1 N4 88.3(2) . 4_666 ? O4 Zn1 N4 116.4(2) . 4_666 ? N1 Zn1 N4 116.3(2) . 4_666 ? O1 Zn1 N4' 113.8(3) . 4_666 ? O4 Zn1 N4' 114.7(3) . 4_666 ? N1 Zn1 N4' 97.5(3) . 4_666 ? N4 Zn1 N4' 26.5(3) 4_666 4_666 ? C2 C1 N1 108.6(4) . . ? C2 C1 H1A 125.7 . . ? N1 C1 H1A 125.7 . . ? C1 C2 N2 106.8(4) . . ? C1 C2 H2A 126.6 . . ? N2 C2 H2A 126.6 . . ? N1 C3 N2 109.9(4) . . ? N1 C3 C4 126.2(4) . . ? N2 C3 C4 123.9(4) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 111.0(4) . . ? N2 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 115.5(4) . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? N3' C7 C6 118.2(5) . . ? N3' C7 N3 38.6(4) . . ? C6 C7 N3 100.8(5) . . ? N3' C7 H7C 125.1 . . ? C6 C7 H7C 111.0 . . ? N3 C7 H7C 111.4 . . ? N3' C7 H7D 73.4 . . ? C6 C7 H7D 112.0 . . ? N3 C7 H7D 112.0 . . ? H7C C7 H7D 109.5 . . ? N3' C7 H7A 107.5 . . ? C6 C7 H7A 107.5 . . ? N3 C7 H7A 82.1 . . ? H7C C7 H7A 31.4 . . ? H7D C7 H7A 134.0 . . ? N3' C7 H7B 108.3 . . ? C6 C7 H7B 107.6 . . ? N3 C7 H7B 145.2 . . ? H7C C7 H7B 76.7 . . ? H7D C7 H7B 38.3 . . ? H7A C7 H7B 107.2 . . ? C11' C8 N3 107.5(17) . . ? C11' C8 C9 18.3(14) . . ? N3 C8 C9 108.3(9) . . ? C11' C8 C10' 67.0(15) . . ? N3 C8 C10' 41.3(6) . . ? C9 C8 C10' 67.4(8) . . ? C11' C8 H8A 125.0 . . ? N3 C8 H8A 125.5 . . ? C9 C8 H8A 126.1 . . ? C10' C8 H8A 166.4 . . ? C11' C8 H11C 93.1 . . ? N3 C8 H11C 123.1 . . ? C9 C8 H11C 77.4 . . ? C10' C8 H11C 116.8 . . ? H8A C8 H11C 71.5 . . ? C11' C8 H11B 61.5 . . ? N3 C8 H11B 107.0 . . ? C9 C8 H11B 79.3 . . ? C10' C8 H11B 94.1 . . ? H8A C8 H11B 87.6 . . ? H11C C8 H11B 129.1 . . ? C11 C8' C9' 3.0(16) . . ? C11 C8' N3' 106.1(19) . . ? C9' C8' N3' 107.7(11) . . ? C11 C8' C10 62.3(16) . . ? C9' C8' C10 64.0(9) . . ? N3' C8' C10 43.8(6) . . ? C11 C8' H8B 130.6 . . ? C9' C8' H8B 128.6 . . ? N3' C8' H8B 122.5 . . ? C10 C8' H8B 165.4 . . ? C11 C8' H11E 41.2 . . ? C9' C8' H11E 38.4 . . ? N3' C8' H11E 112.1 . . ? C10 C8' H11E 79.7 . . ? H8B C8' H11E 106.0 . . ? C11 C8' H11F 30.3 . . ? C9' C8' H11F 31.9 . . ? N3' C8' H11F 117.4 . . ? C10 C8' H11F 77.9 . . ? H8B C8' H11F 116.7 . . ? H11E C8' H11F 66.1 . . ? C11' C9 C8 17.3(13) . . ? C11' C9 N4 106.6(15) . . ? C8 C9 N4 107.9(9) . . ? C11' C9 C10' 65.0(13) . . ? C8 C9 C10' 65.3(8) . . ? N4 C9 C10' 42.8(6) . . ? C11' C9 H11C 42.8 . . ? C8 C9 H11C 27.1 . . ? N4 C9 H11C 120.5 . . ? C10' C9 H11C 82.7 . . ? C11' C9 H9A 129.9 . . ? C8 C9 H9A 129.2 . . ? N4 C9 H9A 122.4 . . ? C10' C9 H9A 165.1 . . ? H11C C9 H9A 109.4 . . ? C11' C9 H11B 26.3 . . ? C8 C9 H11B 42.8 . . ? N4 C9 H11B 111.7 . . ? C10' C9 H11B 77.9 . . ? H11C C9 H11B 64.1 . . ? H9A C9 H11B 114.8 . . ? C11 C9' C8' 3.6(19) . . ? C11 C9' N4' 107(2) . . ? C8' C9' N4' 109.1(11) . . ? C11 C9' C10 67(2) . . ? C8' C9' C10 69.5(9) . . ? N4' C9' C10 39.9(6) . . ? C11 C9' H9B 127.5 . . ? C8' C9' H9B 126.0 . . ? N4' C9' H9B 124.8 . . ? C10 C9' H9B 162.3 . . ? C11 C9' H11E 79.0 . . ? C8' C9' H11E 75.7 . . ? N4' C9' H11E 105.9 . . ? C10 C9' H11E 100.5 . . ? H9B C9' H11E 92.5 . . ? C11 C9' H11F 86.3 . . ? C8' C9' H11F 88.3 . . ? N4' C9' H11F 114.3 . . ? C10 C9' H11F 108.1 . . ? H9B C9' H11F 67.5 . . ? H11E C9' H11F 139.7 . . ? C10' C10 N4' 98(2) . . ? C10' C10 N3' 94(2) . . ? N4' C10 N3' 161.2(14) . . ? C10' C10 N3 53(2) . . ? N4' C10 N3 150.2(14) . . ? N3' C10 N3 45.3(6) . . ? C10' C10 N4 57(2) . . ? N4' C10 N4 43.1(7) . . ? N3' C10 N4 150.6(13) . . ? N3 C10 N4 107.3(10) . . ? C10' C10 C11 165(2) . . ? N4' C10 C11 83.7(12) . . ? N3' C10 C11 81.3(11) . . ? N3 C10 C11 126.0(12) . . ? N4 C10 C11 126.7(12) . . ? C10' C10 C9' 157(3) . . ? N4' C10 C9' 62.1(10) . . ? N3' C10 C9' 102.8(11) . . ? N3 C10 C9' 147.6(11) . . ? N4 C10 C9' 105.1(10) . . ? C11 C10 C9' 21.7(6) . . ? C10' C10 C8' 148(2) . . ? N4' C10 C8' 108.2(12) . . ? N3' C10 C8' 56.5(8) . . ? N3 C10 C8' 101.2(9) . . ? N4 C10 C8' 151.2(11) . . ? C11 C10 C8' 24.9(6) . . ? C9' C10 C8' 46.5(6) . . ? C10 C10' N3 103(2) . . ? C10 C10' N4 98(2) . . ? N3 C10' N4 151.6(15) . . ? C10 C10' N4' 55.1(19) . . ? N3 C10' N4' 157.2(15) . . ? N4 C10' N4' 44.8(7) . . ? C10 C10' N3' 61(2) . . ? N3 C10' N3' 46.2(7) . . ? N4 C10' N3' 159.1(14) . . ? N4' C10' N3' 114.7(13) . . ? C10 C10' C11' 167(2) . . ? N3 C10' C11' 77.4(11) . . ? N4 C10' C11' 78.1(11) . . ? N4' C10' C11' 122.8(13) . . ? N3' C10' C11' 122.5(12) . . ? C10 C10' C8 151(3) . . ? N3 C10' C8 53.4(8) . . ? N4 C10' C8 100.4(11) . . ? N4' C10' C8 144.7(12) . . ? N3' C10' C8 99.4(10) . . ? C11' C10' C8 24.4(5) . . ? C10 C10' C9 147(2) . . ? N3 C10' C9 100.4(11) . . ? N4 C10' C9 53.2(8) . . ? N4' C10' C9 97.9(10) . . ? N3' C10' C9 146.6(12) . . ? C11' C10' C9 25.5(5) . . ? C8 C10' C9 47.4(6) . . ? C9' C11 C8' 173(4) . . ? C9' C11 C10 91(2) . . ? C8' C11 C10 92.8(19) . . ? C9' C11 N4' 54(2) . . ? C8' C11 N4' 130(2) . . ? C10 C11 N4' 37.4(6) . . ? C9' C11 N3' 132(2) . . ? C8' C11 N3' 51.1(15) . . ? C10 C11 N3' 41.7(6) . . ? N4' C11 N3' 78.7(7) . . ? C9' C11 H8B 149.2 . . ? C8' C11 H8B 26.0 . . ? C10 C11 H8B 118.6 . . ? N4' C11 H8B 154.0 . . ? N3' C11 H8B 76.9 . . ? C9' C11 H9B 32.9 . . ? C8' C11 H9B 144.0 . . ? C10 C11 H9B 123.1 . . ? N4' C11 H9B 86.2 . . ? N3' C11 H9B 164.8 . . ? H8B C11 H9B 118.3 . . ? C9' C11 H11E 63.8 . . ? C8' C11 H11E 109.9 . . ? C10 C11 H11E 105.0 . . ? N4' C11 H11E 84.6 . . ? N3' C11 H11E 114.1 . . ? H8B C11 H11E 97.4 . . ? H9B C11 H11E 65.4 . . ? C9' C11 H11F 55.5 . . ? C8' C11 H11F 127.9 . . ? C10 C11 H11F 108.0 . . ? N4' C11 H11F 86.4 . . ? N3' C11 H11F 131.8 . . ? H8B C11 H11F 116.7 . . ? H9B C11 H11F 44.4 . . ? H11E C11 H11F 109.6 . . ? C8 C11' C9 144(3) . . ? C8 C11' C10' 88.6(16) . . ? C9 C11' C10' 89.6(15) . . ? C8 C11' N3 49.5(14) . . ? C9 C11' N3 124.8(16) . . ? C10' C11' N3 39.8(6) . . ? C8 C11' N4 125.5(17) . . ? C9 C11' N4 49.4(12) . . ? C10' C11' N4 41.1(6) . . ? N3 C11' N4 80.1(6) . . ? C8 C11' H8A 32.5 . . ? C9 C11' H8A 137.8 . . ? C10' C11' H8A 120.8 . . ? N3 C11' H8A 81.1 . . ? N4 C11' H8A 156.5 . . ? C8 C11' H11C 41.2 . . ? C9 C11' H11C 106.3 . . ? C10' C11' H11C 106.8 . . ? N3 C11' H11C 78.9 . . ? N4 C11' H11C 121.0 . . ? H8A C11' H11C 40.7 . . ? C8 C11' H9A 138.9 . . ? C9 C11' H9A 25.7 . . ? C10' C11' H9A 115.3 . . ? N3 C11' H9A 148.6 . . ? N4 C11' H9A 74.7 . . ? H8A C11' H9A 117.0 . . ? H11C C11' H9A 98.2 . . ? C8 C11' H11B 79.6 . . ? C9 C11' H11B 134.3 . . ? C10' C11' H11B 108.0 . . ? N3 C11' H11B 91.0 . . ? N4 C11' H11B 126.7 . . ? H8A C11' H11B 67.5 . . ? H11C C11' H11B 108.1 . . ? H9A C11' H11B 119.1 . . ? O2 C12 O1 123.5(4) . . ? O2 C12 C13 120.4(4) . . ? O1 C12 C13 116.1(4) . . ? C14 C13 C15 118.8(4) . . ? C14 C13 C12 121.1(4) . . ? C15 C13 C12 120.1(4) . . ? C13 C14 C15 121.4(4) . 3_657 ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 3_657 . ? C14 C15 C13 119.8(4) 3_657 . ? C14 C15 H15A 120.1 3_657 . ? C13 C15 H15A 120.1 . . ? C19 C16 C18 118.2(4) . . ? C19 C16 C17 120.3(4) . . ? C18 C16 C17 121.4(4) . . ? O3 C17 O4 123.1(4) . . ? O3 C17 C16 120.0(4) . . ? O4 C17 C16 116.8(4) . . ? C19 C18 C16 121.0(4) 3_756 . ? C19 C18 H18A 119.5 3_756 . ? C16 C18 H18A 119.5 . . ? C18 C19 C16 120.7(4) 3_756 . ? C18 C19 H19A 119.6 3_756 . ? C16 C19 H19A 119.6 . . ? C3 N1 C1 106.5(4) . . ? C3 N1 Zn1 127.7(3) . . ? C1 N1 Zn1 124.8(3) . . ? C3 N2 C2 108.3(4) . . ? C3 N2 C5 126.4(4) . . ? C2 N2 C5 125.3(4) . . ? N3' N3 C10' 80.2(10) . . ? N3' N3 C8 163.7(10) . . ? C10' N3 C8 85.3(10) . . ? N3' N3 C10 58.2(7) . . ? C10' N3 C10 24.7(7) . . ? C8 N3 C10 108.7(9) . . ? N3' N3 C7 67.8(7) . . ? C10' N3 C7 147.6(10) . . ? C8 N3 C7 125.6(8) . . ? C10 N3 C7 125.6(8) . . ? N3' N3 C11' 141.1(10) . . ? C10' N3 C11' 62.8(10) . . ? C8 N3 C11' 23.0(5) . . ? C10 N3 C11' 86.9(8) . . ? C7 N3 C11' 146.1(8) . . ? N3 N3' C10 76.5(9) . . ? N3 N3' C10' 53.6(8) . . ? C10 N3' C10' 25.4(6) . . ? N3 N3' C8' 154.1(11) . . ? C10 N3' C8' 79.7(10) . . ? C10' N3' C8' 104.4(10) . . ? N3 N3' C7 73.7(8) . . ? C10 N3' C7 149.4(11) . . ? C10' N3' C7 127.0(10) . . ? C8' N3' C7 127.9(9) . . ? N3 N3' C11 132.6(10) . . ? C10 N3' C11 56.9(9) . . ? C10' N3' C11 81.7(9) . . ? C8' N3' C11 22.8(6) . . ? C7 N3' C11 149.8(8) . . ? N3 N3' H7D 111.4 . . ? C10 N3' H7D 168.4 . . ? C10' N3' H7D 164.7 . . ? C8' N3' H7D 90.8 . . ? C7 N3' H7D 37.8 . . ? C11 N3' H7D 113.5 . . ? N4' N4 C10' 74.5(9) . . ? N4' N4 C10 50.7(8) . . ? C10' N4 C10 24.9(6) . . ? N4' N4 C9 158.4(10) . . ? C10' N4 C9 84.0(9) . . ? C10 N4 C9 107.7(8) . . ? N4' N4 C11' 135.1(10) . . ? C10' N4 C11' 60.8(9) . . ? C10 N4 C11' 85.2(8) . . ? C9 N4 C11' 23.9(5) . . ? N4' N4 Zn1 78.7(7) . 4_465 ? C10' N4 Zn1 151.4(9) . 4_465 ? C10 N4 Zn1 129.4(8) . 4_465 ? C9 N4 Zn1 122.8(6) . 4_465 ? C11' N4 Zn1 143.9(6) . 4_465 ? N4 N4' C10 86.2(11) . . ? N4 N4' C10' 60.7(9) . . ? C10 N4' C10' 26.7(7) . . ? N4 N4' C9' 163.9(11) . . ? C10 N4' C9' 78.1(11) . . ? C10' N4' C9' 104.1(11) . . ? N4 N4' C11 145.1(11) . . ? C10 N4' C11 58.9(10) . . ? C10' N4' C11 84.9(10) . . ? C9' N4' C11 19.2(6) . . ? N4 N4' Zn1 74.8(7) . 4_465 ? C10 N4' Zn1 160.9(12) . 4_465 ? C10' N4' Zn1 134.5(10) . 4_465 ? C9' N4' Zn1 121.0(8) . 4_465 ? C11 N4' Zn1 140.1(8) . 4_465 ? C12 O1 Zn1 119.4(3) . . ? H1WA O1W H1WB 110.4 . . ? H2WA O2W H2WB 113.2 . . ? H3WA O3W H3WB 108.0 . . ? C17 O4 Zn1 117.9(3) . . ? 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 O3W 0.84 1.92 2.754(7) 170.2 . O1W H1WB O4 0.84 2.06 2.892(6) 169.9 2_656 O2W H2WA O2 0.78 1.95 2.717(6) 165.1 . O2W H2WB O3 0.87 1.90 2.760(6) 167.9 1_455 O3W H3WA O1W 0.85 1.95 2.775(7) 163.8 3_667 O3W H3WB O2W 0.85 1.86 2.686(7) 163.4 4_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.650 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.090