# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_182-ka _database_code_depnum_ccdc_archive 'CCDC 896830' #TrackingRef '182-ka_tmp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N O6 Zn, 3(C3 H7 N O), C2 H8 N' _chemical_formula_sum 'C25 H42 N5 O9 Zn' _chemical_formula_weight 622.01 _chemical_absolute_configuration ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 17.546(3) _cell_length_b 11.158(2) _cell_length_c 18.392(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.33(2) _cell_angle_gamma 90.00 _cell_volume 3169.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 1.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.695 _exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_type 'RAPID II large area curved imaging plate detector ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12440 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0806 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 66.98 _reflns_number_total 5351 _reflns_number_gt 3795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0681P)^2^+1.2670P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5344 _refine_ls_number_parameters 377 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1810 _refine_ls_wR_factor_gt 0.1491 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 0.83923(3) 0.16180(4) 0.66285(3) 0.0402(2) Uani 1 1 d . . . O1 O 0.87436(18) 0.0807(3) 0.59224(18) 0.0531(8) Uani 1 1 d . . . O2 O 1.00115(19) 0.1740(2) 0.67048(19) 0.0526(8) Uani 1 1 d . . . O3 O 0.72853(17) 0.0742(3) 0.60200(19) 0.0557(8) Uani 1 1 d . . . O4 O 0.67077(19) 0.2162(3) 0.6401(2) 0.0722(10) Uani 1 1 d . . . O5 O 0.90095(17) 0.1511(2) 0.78942(17) 0.0459(7) Uani 1 1 d . . . O6 O 0.9092(3) -0.0418(3) 0.7691(2) 0.0902(13) Uani 1 1 d . . . N1 N 0.8222(3) 0.3422(3) 0.6417(3) 0.0771(14) Uani 1 1 d . . . H1N H 0.7804 0.3169 0.6480 0.116 Uiso 1 1 d R . . C101 C 0.7944(4) 0.3802(5) 0.5554(3) 0.0809(16) Uani 1 1 d . . . H10A H 0.7838 0.4668 0.5504 0.121 Uiso 1 1 calc R . . H10B H 0.7411 0.3380 0.5179 0.121 Uiso 1 1 calc R . . H10C H 0.8400 0.3611 0.5408 0.121 Uiso 1 1 calc R . . C102 C 0.8812(4) 0.4169(5) 0.7079(4) 0.0899(18) Uani 1 1 d . . . H10D H 0.9385 0.4132 0.7110 0.135 Uiso 1 1 calc R . . H10E H 0.8853 0.3888 0.7601 0.135 Uiso 1 1 calc R . . H10F H 0.8602 0.4998 0.6979 0.135 Uiso 1 1 calc R . . C1 C 0.9513(3) 0.1065(4) 0.6115(3) 0.0419(10) Uani 1 1 d . . . C2 C 0.9760(2) 0.0501(3) 0.5536(2) 0.0381(9) Uani 1 1 d . . . C3 C 0.9191(2) -0.0239(3) 0.4852(2) 0.0393(9) Uani 1 1 d . . . H3 H 0.8623 -0.0389 0.4770 0.047 Uiso 1 1 calc . . . C4 C 1.0569(2) 0.0729(3) 0.5679(2) 0.0411(9) Uani 1 1 d . . . H4 H 1.0954 0.1210 0.6131 0.049 Uiso 1 1 calc R . . C5 C 0.6651(3) 0.1224(4) 0.6018(3) 0.0488(11) Uani 1 1 d . . . C6 C 0.5797(2) 0.0578(4) 0.5485(2) 0.0414(9) Uani 1 1 d . . . C7 C 0.5678(3) -0.0317(4) 0.4920(3) 0.0482(10) Uani 1 1 d . . . H7 H 0.6163 -0.0551 0.4855 0.058 Uiso 1 1 calc R . . C8 C 0.5109(3) 0.0900(4) 0.5562(3) 0.0482(10) Uani 1 1 d . . . H8 H 0.5152 0.1514 0.5937 0.058 Uiso 1 1 calc R . . C9 C 0.9224(3) 0.0437(4) 0.8171(3) 0.0491(11) Uani 1 1 d . . . C10 C 0.9639(2) 0.0229(3) 0.9122(2) 0.0390(9) Uani 1 1 d . . . C11 C 0.9776(3) 0.1161(4) 0.9682(3) 0.0435(10) Uani 1 1 d . . . H11 H 0.9629 0.1958 0.9482 0.052 Uiso 1 1 calc R . . C12 C 0.9864(3) -0.0935(4) 0.9447(3) 0.0455(10) Uani 1 1 d . . . H12 H 0.9778 -0.1587 0.9084 0.055 Uiso 1 1 calc R . . N2 N 0.6804(3) -0.1798(4) 0.8268(3) 0.0636(11) Uani 1 1 d . . . C15 C 0.6113(4) -0.1310(6) 0.7440(4) 0.0912(19) Uani 1 1 d . . . H15A H 0.5563 -0.1721 0.7283 0.137 Uiso 1 1 calc R . . H15B H 0.6291 -0.1447 0.7017 0.137 Uiso 1 1 calc R . . H15C H 0.6040 -0.0448 0.7490 0.137 Uiso 1 1 calc R . . C16 C 0.7668(4) -0.1304(6) 0.8640(4) 0.107(2) Uani 1 1 d . . . H16A H 0.8054 -0.1801 0.9111 0.161 Uiso 1 1 calc R . . H16B H 0.7659 -0.0486 0.8829 0.161 Uiso 1 1 calc R . . H16C H 0.7877 -0.1291 0.8231 0.161 Uiso 1 1 calc R . . C17 C 0.6662(3) -0.2652(5) 0.8670(3) 0.0673(14) Uani 1 1 d . . . H17 H 0.6094 -0.2978 0.8419 0.081 Uiso 1 1 calc R . . O7 O 0.7206(2) -0.3102(4) 0.9368(2) 0.0857(11) Uani 1 1 d . . . N3 N 0.6858(3) 0.2976(4) 0.8375(2) 0.0606(10) Uani 1 1 d . . . C18 C 0.7696(3) 0.3082(6) 0.8487(4) 0.0905(19) Uani 1 1 d . . . H18A H 0.7809 0.2434 0.8191 0.136 Uiso 1 1 calc R . . H18B H 0.8109 0.3030 0.9077 0.136 Uiso 1 1 calc R . . H18C H 0.7761 0.3856 0.8271 0.136 Uiso 1 1 calc R . . C19 C 0.6631(4) 0.3905(5) 0.8769(4) 0.098(2) Uani 1 1 d . . . H19A H 0.6091 0.3692 0.8775 0.147 Uiso 1 1 calc R . . H19B H 0.6550 0.4657 0.8466 0.147 Uiso 1 1 calc R . . H19C H 0.7095 0.4003 0.9338 0.147 Uiso 1 1 calc R . . C20 C 0.6306(3) 0.2117(5) 0.7903(3) 0.0612(12) Uani 1 1 d . . . H20 H 0.6530 0.1545 0.7671 0.073 Uiso 1 1 calc R . . O8 O 0.5574(2) 0.1994(4) 0.7744(2) 0.0886(12) Uani 1 1 d . . . N4 N 0.4694(4) 0.0332(4) 0.8911(3) 0.0831(14) Uani 1 1 d . . . C21 C 0.5322(5) -0.0389(6) 0.8887(5) 0.126(3) Uani 1 1 d . . . H21A H 0.5052 -0.1117 0.8571 0.189 Uiso 1 1 calc R . . H21B H 0.5749 -0.0608 0.9452 0.189 Uiso 1 1 calc R . . H21C H 0.5610 0.0046 0.8623 0.189 Uiso 1 1 calc R . . C22 C 0.4962(6) 0.1492(5) 0.9326(5) 0.132(3) Uani 1 1 d . . . H22A H 0.5120 0.2028 0.8997 0.198 Uiso 1 1 calc R . . H22B H 0.5463 0.1380 0.9873 0.198 Uiso 1 1 calc R . . H22C H 0.4484 0.1845 0.9386 0.198 Uiso 1 1 calc R . . C23 C 0.3901(5) -0.0069(7) 0.8581(5) 0.117(3) Uani 1 1 d . . . H23 H 0.3784 -0.0809 0.8293 0.140 Uiso 1 1 calc R . . O9 O 0.3316(4) 0.0413(6) 0.8610(4) 0.188(3) Uani 1 1 d . . . N5 N 0.8269(3) -0.1679(3) 0.6192(2) 0.0479(9) Uani 1 1 d . . . H5AN H 0.799(3) -0.129(4) 0.571(3) 0.057 Uiso 1 1 d . . . H5BN H 0.857(3) -0.106(4) 0.662(3) 0.057 Uiso 1 1 d . . . C13 C 0.8986(3) -0.2383(4) 0.6267(3) 0.0571(12) Uani 1 1 d . . . H13A H 0.9308 -0.2694 0.6831 0.086 Uiso 1 1 calc R . . H13B H 0.9370 -0.1883 0.6144 0.086 Uiso 1 1 calc R . . H13C H 0.8772 -0.3054 0.5877 0.086 Uiso 1 1 calc R . . C14 C 0.7722(3) -0.2377(5) 0.6392(4) 0.0813(17) Uani 1 1 d . . . H14A H 0.7483 -0.3043 0.6000 0.122 Uiso 1 1 calc R . . H14B H 0.7249 -0.1877 0.6361 0.122 Uiso 1 1 calc R . . H14C H 0.8056 -0.2694 0.6953 0.122 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 0.0428(4) 0.0401(4) 0.0456(4) -0.0017(2) 0.0275(3) -0.0014(2) O1 0.0529(18) 0.0584(19) 0.064(2) -0.0065(15) 0.0404(16) -0.0056(15) O2 0.065(2) 0.0520(18) 0.060(2) -0.0194(15) 0.0450(17) -0.0152(15) O3 0.0417(16) 0.0582(19) 0.074(2) -0.0132(16) 0.0330(16) -0.0036(14) O4 0.054(2) 0.080(2) 0.098(3) -0.037(2) 0.048(2) -0.0157(18) O5 0.0538(18) 0.0479(17) 0.0453(18) 0.0032(13) 0.0310(15) 0.0011(13) O6 0.165(4) 0.053(2) 0.050(2) -0.0078(17) 0.049(2) 0.009(2) N1 0.127(4) 0.045(2) 0.064(3) 0.001(2) 0.050(3) -0.013(2) C101 0.116(5) 0.067(3) 0.074(4) 0.019(3) 0.057(4) 0.010(3) C102 0.090(4) 0.055(3) 0.093(4) -0.002(3) 0.018(4) -0.013(3) C1 0.049(2) 0.038(2) 0.052(3) 0.008(2) 0.035(2) 0.0014(19) C2 0.041(2) 0.039(2) 0.045(2) -0.0002(18) 0.0295(19) 0.0034(18) C3 0.041(2) 0.043(2) 0.041(2) -0.0017(18) 0.0253(19) -0.0038(18) C4 0.040(2) 0.043(2) 0.041(2) -0.0093(18) 0.0198(19) -0.0053(18) C5 0.046(3) 0.058(3) 0.051(3) 0.008(2) 0.030(2) 0.002(2) C6 0.036(2) 0.050(2) 0.041(2) -0.0014(19) 0.0210(19) -0.0005(19) C7 0.040(2) 0.055(3) 0.058(3) 0.000(2) 0.031(2) 0.002(2) C8 0.043(2) 0.052(3) 0.057(3) -0.003(2) 0.030(2) 0.002(2) C9 0.055(3) 0.051(3) 0.047(3) -0.006(2) 0.028(2) -0.006(2) C10 0.042(2) 0.042(2) 0.036(2) 0.0067(18) 0.0203(19) 0.0015(18) C11 0.053(3) 0.037(2) 0.048(3) -0.0006(19) 0.029(2) 0.0018(19) C12 0.051(3) 0.043(2) 0.049(3) -0.003(2) 0.029(2) 0.000(2) N2 0.055(3) 0.076(3) 0.061(3) 0.005(2) 0.029(2) -0.003(2) C15 0.083(4) 0.106(5) 0.089(4) 0.030(4) 0.044(4) 0.004(4) C16 0.072(4) 0.140(6) 0.111(5) 0.006(5) 0.045(4) -0.027(4) C17 0.056(3) 0.074(4) 0.069(4) -0.002(3) 0.027(3) 0.000(3) O7 0.080(3) 0.101(3) 0.066(3) 0.018(2) 0.026(2) 0.004(2) N3 0.057(2) 0.067(3) 0.064(3) -0.012(2) 0.033(2) -0.004(2) C18 0.066(4) 0.123(5) 0.088(4) -0.029(4) 0.040(3) -0.022(4) C19 0.093(5) 0.090(4) 0.118(5) -0.040(4) 0.056(4) 0.002(4) C20 0.070(3) 0.063(3) 0.062(3) -0.004(3) 0.040(3) -0.004(3) O8 0.076(3) 0.102(3) 0.108(3) -0.019(2) 0.061(3) -0.022(2) N4 0.104(4) 0.074(3) 0.088(4) -0.002(3) 0.060(3) -0.001(3) C21 0.134(6) 0.113(6) 0.191(8) -0.020(5) 0.127(6) -0.009(5) C22 0.233(10) 0.067(4) 0.118(6) -0.008(4) 0.103(7) -0.022(5) C23 0.109(6) 0.123(6) 0.112(6) -0.023(5) 0.048(5) 0.034(5) O9 0.119(4) 0.217(7) 0.206(6) -0.059(5) 0.061(4) 0.074(4) N5 0.061(3) 0.038(2) 0.049(2) 0.0004(16) 0.030(2) -0.0004(17) C13 0.052(3) 0.057(3) 0.064(3) 0.012(2) 0.029(2) 0.010(2) C14 0.084(4) 0.067(3) 0.125(5) 0.013(3) 0.077(4) -0.003(3) _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 1.909(3) . ? Zn1 O3 1.979(3) . ? Zn1 N1 2.045(4) . ? Zn1 O5 2.053(3) . ? Zn1 H1N 1.9671 . ? O1 C1 1.256(4) . ? O2 C1 1.269(5) . ? O3 C5 1.234(4) . ? O4 C5 1.240(5) . ? O5 C9 1.286(5) . ? O6 C9 1.244(5) . ? N1 C102 1.434(6) . ? N1 C101 1.485(6) . ? N1 H1N 0.8436 . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? C102 H10D 0.9800 . ? C102 H10E 0.9800 . ? C102 H10F 0.9800 . ? C1 C2 1.468(5) . ? C2 C4 1.339(5) . ? C2 C3 1.439(5) . ? C3 C4 1.348(5) 3_756 ? C3 H3 0.9500 . ? C4 C3 1.348(5) 3_756 ? C4 H4 0.9500 . ? C5 C6 1.526(6) . ? C6 C8 1.330(5) . ? C6 C7 1.384(5) . ? C7 C8 1.398(5) 3_656 ? C7 H7 0.9500 . ? C8 C7 1.398(5) 3_656 ? C8 H8 0.9500 . ? C9 C10 1.560(5) . ? C10 C11 1.402(5) . ? C10 C12 1.406(5) . ? C11 C12 1.438(5) 3_757 ? C11 H11 0.9500 . ? C12 C11 1.438(5) 3_757 ? C12 H12 0.9500 . ? N2 C17 1.301(6) . ? N2 C16 1.443(6) . ? N2 C15 1.527(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O7 1.284(5) . ? C17 H17 0.9500 . ? N3 C20 1.346(6) . ? N3 C18 1.390(6) . ? N3 C19 1.426(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O8 1.182(5) . ? C20 H20 0.9500 . ? N4 C23 1.305(8) . ? N4 C21 1.382(7) . ? N4 C22 1.462(7) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O9 1.182(7) . ? C23 H23 0.9500 . ? N5 C14 1.413(5) . ? N5 C13 1.433(5) . ? N5 H5AN 0.90(4) . ? N5 H5BN 0.99(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 O3 85.89(12) . . ? O1 Zn1 N1 113.72(15) . . ? O3 Zn1 N1 111.25(17) . . ? O1 Zn1 O5 125.24(12) . . ? O3 Zn1 O5 117.42(12) . . ? N1 Zn1 O5 102.95(14) . . ? O1 Zn1 H1N 129.8 . . ? O3 Zn1 H1N 92.7 . . ? N1 Zn1 H1N 24.2 . . ? O5 Zn1 H1N 99.7 . . ? C1 O1 Zn1 110.5(3) . . ? C5 O3 Zn1 115.4(3) . . ? C9 O5 Zn1 113.6(3) . . ? C102 N1 C101 118.7(4) . . ? C102 N1 Zn1 115.4(3) . . ? C101 N1 Zn1 115.4(3) . . ? C102 N1 H1N 113.7 . . ? C101 N1 H1N 112.2 . . ? Zn1 N1 H1N 72.8 . . ? N1 C101 H10A 109.5 . . ? N1 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? N1 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? N1 C102 H10D 109.5 . . ? N1 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? N1 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? O1 C1 O2 126.1(4) . . ? O1 C1 C2 110.2(4) . . ? O2 C1 C2 123.6(3) . . ? C4 C2 C3 120.8(3) . . ? C4 C2 C1 115.2(4) . . ? C3 C2 C1 124.0(3) . . ? C4 C3 C2 122.7(3) 3_756 . ? C4 C3 H3 118.6 3_756 . ? C2 C3 H3 118.6 . . ? C2 C4 C3 116.5(4) . 3_756 ? C2 C4 H4 121.7 . . ? C3 C4 H4 121.7 3_756 . ? O3 C5 O4 122.4(4) . . ? O3 C5 C6 113.9(4) . . ? O4 C5 C6 123.6(4) . . ? C8 C6 C7 117.0(4) . . ? C8 C6 C5 117.9(4) . . ? C7 C6 C5 125.1(3) . . ? C6 C7 C8 124.3(4) . 3_656 ? C6 C7 H7 117.9 . . ? C8 C7 H7 117.9 3_656 . ? C6 C8 C7 118.7(4) . 3_656 ? C6 C8 H8 120.6 . . ? C7 C8 H8 120.6 3_656 . ? O6 C9 O5 120.8(4) . . ? O6 C9 C10 120.8(4) . . ? O5 C9 C10 118.4(4) . . ? C11 C10 C12 117.2(4) . . ? C11 C10 C9 122.6(4) . . ? C12 C10 C9 120.1(4) . . ? C10 C11 C12 121.4(4) . 3_757 ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 3_757 . ? C10 C12 C11 121.4(4) . 3_757 ? C10 C12 H12 119.3 . . ? C11 C12 H12 119.3 3_757 . ? C17 N2 C16 116.8(5) . . ? C17 N2 C15 123.5(4) . . ? C16 N2 C15 119.7(5) . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O7 C17 N2 127.1(5) . . ? O7 C17 H17 116.5 . . ? N2 C17 H17 116.5 . . ? C20 N3 C18 122.8(4) . . ? C20 N3 C19 123.8(4) . . ? C18 N3 C19 113.2(4) . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 C20 N3 127.3(5) . . ? O8 C20 H20 116.3 . . ? N3 C20 H20 116.3 . . ? C23 N4 C21 118.5(6) . . ? C23 N4 C22 123.7(6) . . ? C21 N4 C22 117.9(6) . . ? N4 C21 H21A 109.5 . . ? N4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N4 C22 H22A 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O9 C23 N4 125.5(8) . . ? O9 C23 H23 117.3 . . ? N4 C23 H23 117.3 . . ? C14 N5 C13 110.3(4) . . ? C14 N5 H5AN 114(3) . . ? C13 N5 H5AN 114(3) . . ? C14 N5 H5BN 110(2) . . ? C13 N5 H5BN 101(2) . . ? H5AN N5 H5BN 107(4) . . ? N5 C13 H13A 109.5 . . ? N5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 H14A 109.5 . . ? N5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O3 Zn1 O1 C1 -177.1(3) . . . . ? N1 Zn1 O1 C1 71.5(3) . . . . ? O5 Zn1 O1 C1 -56.1(3) . . . . ? O1 Zn1 O3 C5 -154.9(3) . . . . ? N1 Zn1 O3 C5 -41.1(3) . . . . ? O5 Zn1 O3 C5 77.1(3) . . . . ? O1 Zn1 O5 C9 -44.7(3) . . . . ? O3 Zn1 O5 C9 60.8(3) . . . . ? N1 Zn1 O5 C9 -176.6(3) . . . . ? O1 Zn1 N1 C102 -114.6(4) . . . . ? O3 Zn1 N1 C102 150.4(4) . . . . ? O5 Zn1 N1 C102 23.8(4) . . . . ? O1 Zn1 N1 C101 29.9(4) . . . . ? O3 Zn1 N1 C101 -65.1(4) . . . . ? O5 Zn1 N1 C101 168.3(4) . . . . ? Zn1 O1 C1 O2 1.8(5) . . . . ? Zn1 O1 C1 C2 -176.3(2) . . . . ? O1 C1 C2 C4 179.3(3) . . . . ? O2 C1 C2 C4 1.2(6) . . . . ? O1 C1 C2 C3 -0.1(5) . . . . ? O2 C1 C2 C3 -178.3(4) . . . . ? C4 C2 C3 C4 -0.6(7) . . . 3_756 ? C1 C2 C3 C4 178.8(4) . . . 3_756 ? C3 C2 C4 C3 0.6(6) . . . 3_756 ? C1 C2 C4 C3 -178.9(3) . . . 3_756 ? Zn1 O3 C5 O4 -3.2(6) . . . . ? Zn1 O3 C5 C6 175.2(2) . . . . ? O3 C5 C6 C8 168.0(4) . . . . ? O4 C5 C6 C8 -13.5(6) . . . . ? O3 C5 C6 C7 -12.4(6) . . . . ? O4 C5 C6 C7 166.1(4) . . . . ? C8 C6 C7 C8 -0.5(7) . . . 3_656 ? C5 C6 C7 C8 179.9(4) . . . 3_656 ? C7 C6 C8 C7 0.5(7) . . . 3_656 ? C5 C6 C8 C7 -179.9(4) . . . 3_656 ? Zn1 O5 C9 O6 3.1(5) . . . . ? Zn1 O5 C9 C10 -175.7(2) . . . . ? O6 C9 C10 C11 -178.1(4) . . . . ? O5 C9 C10 C11 0.8(6) . . . . ? O6 C9 C10 C12 -0.3(6) . . . . ? O5 C9 C10 C12 178.5(4) . . . . ? C12 C10 C11 C12 0.2(6) . . . 3_757 ? C9 C10 C11 C12 178.1(3) . . . 3_757 ? C11 C10 C12 C11 -0.2(6) . . . 3_757 ? C9 C10 C12 C11 -178.1(3) . . . 3_757 ? C16 N2 C17 O7 0.5(8) . . . . ? C15 N2 C17 O7 -179.4(5) . . . . ? C18 N3 C20 O8 -176.3(5) . . . . ? C19 N3 C20 O8 -0.1(9) . . . . ? C21 N4 C23 O9 174.1(8) . . . . ? C22 N4 C23 O9 -4.1(13) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.753 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.075