# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_bbb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H36 N6 O16 Zn3' _chemical_formula_weight 1076.88 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.205(6) _cell_length_b 24.834(8) _cell_length_c 13.514(5) _cell_angle_alpha 90.00 _cell_angle_beta 124.244(3) _cell_angle_gamma 90.00 _cell_volume 4496(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6566 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 1.666 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6177 _exptl_absorpt_correction_T_max 0.7649 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12933 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4138 _reflns_number_gt 3619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+4.2066P] 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 4138 _refine_ls_number_parameters 321 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.055 _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 C21 C 0.9778(8) 0.9936(6) 0.1445(11) 0.155(5) Uani 0.50 1 d PDU A -1 H21A H 0.9815 1.0264 0.1084 0.186 Uiso 0.50 1 calc PR A -1 H21B H 1.0165 0.9660 0.1373 0.186 Uiso 0.50 1 calc PR A -1 C22 C 1.0189(19) 1.0033(6) 0.2780(13) 0.173(6) Uani 0.50 1 d PDU A -1 H22A H 0.9903 1.0356 0.2853 0.260 Uiso 0.50 1 calc PR A -1 H22B H 1.0902 1.0069 0.3234 0.260 Uiso 0.50 1 calc PR A -1 H22C H 1.0017 0.9733 0.3079 0.260 Uiso 0.50 1 calc PR A -1 O9 O 0.8768(5) 0.9768(3) 0.0864(7) 0.136(3) Uani 0.50 1 d PDU A -1 H9 H 0.8384 1.0004 0.0357 0.204 Uiso 0.50 1 d PR A -1 Zn1 Zn 0.5000 0.0000 0.0000 0.02331(10) Uani 1 2 d S . . Zn2 Zn 0.322511(19) 0.052506(10) -0.27160(2) 0.02711(9) Uani 1 1 d . . . O1 O 0.74207(13) 0.06221(7) -0.05421(14) 0.0385(4) Uani 1 1 d . . . O2 O 0.62419(14) 0.12105(8) -0.09242(16) 0.0499(5) Uani 1 1 d . . . O3 O 0.65123(12) 0.02988(6) 0.08091(13) 0.0340(4) Uani 1 1 d . . . O4 O 0.75197(13) 0.01222(7) 0.27671(14) 0.0400(4) Uani 1 1 d . . . O5 O 0.9700(2) 0.15628(15) 0.5361(2) 0.1150(13) Uani 1 1 d . . . O6 O 1.0160(2) 0.21801(11) 0.4691(2) 0.0972(10) Uani 1 1 d . . . O7 O 0.45881(12) 0.03861(6) -0.15488(13) 0.0297(3) Uani 1 1 d . . . H7D H 0.4975 0.0616 -0.1552 0.061(10) Uiso 1 1 d R . . O8 O 0.5000 0.20238(11) 0.7500 0.0685(9) Uani 1 2 d S . . H1W H 0.4636 0.1823 0.6895 0.079(12) Uiso 1 1 d R . . N1 N 0.96730(19) 0.17845(11) 0.4549(2) 0.0570(7) Uani 1 1 d . . . N2 N 0.45984(14) 0.07047(7) 0.05932(16) 0.0294(4) Uani 1 1 d . . . N3 N 0.23892(15) 0.38414(7) 0.23500(17) 0.0321(4) Uani 1 1 d . . . C1 C 0.77125(17) 0.11771(9) 0.10448(19) 0.0288(5) Uani 1 1 d . . . C2 C 0.78330(17) 0.08986(9) 0.20186(19) 0.0277(5) Uani 1 1 d . . . C3 C 0.84886(18) 0.10949(10) 0.3174(2) 0.0349(5) Uani 1 1 d . . . H3 H 0.8584 0.0911 0.3830 0.042 Uiso 1 1 calc R . . C4 C 0.89959(18) 0.15690(10) 0.3328(2) 0.0384(6) Uani 1 1 d . . . C5 C 0.8885(2) 0.18572(10) 0.2387(2) 0.0428(6) Uani 1 1 d . . . H5 H 0.9232 0.2177 0.2517 0.051 Uiso 1 1 calc R . . C6 C 0.8241(2) 0.16546(10) 0.1244(2) 0.0402(6) Uani 1 1 d . . . H6 H 0.8157 0.1840 0.0596 0.048 Uiso 1 1 calc R . . C7 C 0.70465(18) 0.09846(9) -0.02403(19) 0.0323(5) Uani 1 1 d . . . C8 C 0.72341(17) 0.03987(8) 0.18355(19) 0.0266(5) Uani 1 1 d . . . C9 C 0.47972(18) 0.12112(9) 0.04483(19) 0.0311(5) Uani 1 1 d . . . H9A H 0.5178 0.1265 0.0138 0.037 Uiso 1 1 calc R . . C10 C 0.44626(19) 0.16581(9) 0.0739(2) 0.0343(5) Uani 1 1 d . . . H10 H 0.4622 0.2003 0.0628 0.041 Uiso 1 1 calc R . . C11 C 0.38821(18) 0.15869(9) 0.1200(2) 0.0330(5) Uani 1 1 d . . . C12 C 0.36784(19) 0.10600(10) 0.1342(2) 0.0367(5) Uani 1 1 d . . . H12 H 0.3294 0.0993 0.1643 0.044 Uiso 1 1 calc R . . C13 C 0.40453(19) 0.06363(9) 0.1038(2) 0.0349(5) Uani 1 1 d . . . H13 H 0.3903 0.0287 0.1146 0.042 Uiso 1 1 calc R . . C14 C 0.34849(19) 0.20299(10) 0.1539(2) 0.0396(6) Uani 1 1 d . . . H14 H 0.3082 0.1935 0.1799 0.048 Uiso 1 1 calc R . . C15 C 0.36448(19) 0.25486(10) 0.1509(2) 0.0386(6) Uani 1 1 d . . . H15 H 0.4059 0.2646 0.1267 0.046 Uiso 1 1 calc R . . C16 C 0.2946(2) 0.39267(10) 0.1915(2) 0.0394(6) Uani 1 1 d . . . H16 H 0.3054 0.4280 0.1784 0.047 Uiso 1 1 calc R . . C17 C 0.3364(2) 0.35165(10) 0.1654(2) 0.0412(6) Uani 1 1 d . . . H17 H 0.3746 0.3597 0.1357 0.049 Uiso 1 1 calc R . . C18 C 0.32190(18) 0.29875(10) 0.1829(2) 0.0344(5) Uani 1 1 d . . . C19 C 0.2651(2) 0.28988(10) 0.2298(3) 0.0458(6) Uani 1 1 d . . . H19 H 0.2544 0.2550 0.2453 0.055 Uiso 1 1 calc R . . C20 C 0.2250(2) 0.33299(10) 0.2530(2) 0.0440(6) Uani 1 1 d . . . H20 H 0.1862 0.3262 0.2826 0.053 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 C21 0.110(6) 0.153(9) 0.180(9) 0.012(7) 0.067(7) 0.003(6) C22 0.138(10) 0.203(10) 0.210(9) -0.020(9) 0.117(7) -0.019(8) O9 0.090(4) 0.124(5) 0.175(6) 0.087(4) 0.063(4) 0.014(3) Zn1 0.02948(19) 0.01907(18) 0.02407(18) -0.00047(13) 0.01669(15) 0.00065(13) Zn2 0.03459(16) 0.02274(14) 0.02764(14) 0.00229(9) 0.01971(12) 0.00457(10) O1 0.0488(10) 0.0409(10) 0.0298(8) -0.0075(7) 0.0245(8) -0.0050(8) O2 0.0480(11) 0.0448(11) 0.0406(10) 0.0073(8) 0.0149(9) 0.0048(9) O3 0.0356(9) 0.0371(9) 0.0292(8) -0.0050(7) 0.0182(7) -0.0137(7) O4 0.0460(10) 0.0345(9) 0.0333(9) 0.0051(7) 0.0186(8) -0.0090(8) O5 0.130(3) 0.167(3) 0.0490(14) -0.0491(17) 0.0508(16) -0.094(2) O6 0.107(2) 0.0830(19) 0.0732(16) -0.0381(14) 0.0331(15) -0.0587(17) O7 0.0335(8) 0.0286(8) 0.0307(8) 0.0067(6) 0.0202(7) 0.0031(7) O8 0.0630(19) 0.0301(15) 0.082(2) 0.000 0.0225(18) 0.000 N1 0.0548(15) 0.0662(17) 0.0487(14) -0.0285(13) 0.0283(12) -0.0245(13) N2 0.0398(11) 0.0231(9) 0.0311(9) -0.0005(8) 0.0234(9) 0.0025(8) N3 0.0373(11) 0.0279(10) 0.0343(10) -0.0004(8) 0.0220(9) 0.0062(8) C1 0.0331(12) 0.0258(11) 0.0324(11) -0.0044(9) 0.0213(10) -0.0032(9) C2 0.0307(11) 0.0265(11) 0.0303(11) -0.0047(9) 0.0198(10) -0.0023(9) C3 0.0384(13) 0.0384(13) 0.0323(12) -0.0083(10) 0.0226(11) -0.0070(10) C4 0.0375(13) 0.0417(14) 0.0394(13) -0.0198(11) 0.0238(11) -0.0123(11) C5 0.0466(15) 0.0318(13) 0.0557(16) -0.0127(12) 0.0322(13) -0.0154(11) C6 0.0507(15) 0.0324(13) 0.0438(14) -0.0031(11) 0.0304(13) -0.0121(11) C7 0.0416(14) 0.0284(12) 0.0284(11) 0.0005(9) 0.0207(11) -0.0098(10) C8 0.0328(12) 0.0228(11) 0.0302(11) -0.0029(9) 0.0214(10) -0.0001(9) C9 0.0411(13) 0.0269(11) 0.0321(11) -0.0004(9) 0.0246(11) -0.0005(9) C10 0.0462(14) 0.0211(11) 0.0357(12) -0.0004(9) 0.0232(11) 0.0011(10) C11 0.0371(13) 0.0297(12) 0.0320(11) -0.0016(9) 0.0192(11) 0.0061(10) C12 0.0443(14) 0.0343(13) 0.0453(13) -0.0010(11) 0.0335(12) 0.0031(11) C13 0.0485(15) 0.0252(12) 0.0426(13) 0.0002(10) 0.0327(12) 0.0007(10) C14 0.0440(15) 0.0349(13) 0.0457(14) -0.0023(11) 0.0288(12) 0.0058(11) C15 0.0439(14) 0.0348(13) 0.0418(13) -0.0012(11) 0.0269(12) 0.0086(11) C16 0.0515(15) 0.0277(12) 0.0497(14) -0.0008(11) 0.0351(13) 0.0024(11) C17 0.0508(16) 0.0346(14) 0.0554(15) -0.0011(11) 0.0403(14) 0.0029(11) C18 0.0360(13) 0.0332(13) 0.0331(12) -0.0025(10) 0.0188(11) 0.0072(10) C19 0.0644(18) 0.0246(12) 0.0654(17) 0.0021(12) 0.0468(16) 0.0055(12) C20 0.0601(17) 0.0331(14) 0.0594(16) 0.0011(12) 0.0462(15) 0.0037(12) _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 C21 O9 1.421(9) . ? C21 C22 1.550(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O9 H9 0.8500 . ? Zn1 O7 2.0429(15) 5_655 ? Zn1 O7 2.0429(15) . ? Zn1 N2 2.1717(18) 5_655 ? Zn1 N2 2.1717(18) . ? Zn1 O3 2.1763(17) 5_655 ? Zn1 O3 2.1763(17) . ? Zn2 O7 1.8881(16) . ? Zn2 O1 1.9805(17) 2_654 ? Zn2 O4 1.9877(17) 5_655 ? Zn2 N3 2.0652(19) 7 ? O1 C7 1.274(3) . ? O1 Zn2 1.9805(17) 2_654 ? O2 C7 1.230(3) . ? O3 C8 1.236(3) . ? O4 C8 1.271(3) . ? O4 Zn2 1.9877(17) 5_655 ? O5 N1 1.207(4) . ? O6 N1 1.206(3) . ? O7 H7D 0.8499 . ? O8 H1W 0.8499 . ? N1 C4 1.474(3) . ? N2 C9 1.340(3) . ? N2 C13 1.342(3) . ? N3 C20 1.336(3) . ? N3 C16 1.342(3) . ? N3 Zn2 2.0652(19) 7 ? C1 C6 1.397(3) . ? C1 C2 1.400(3) . ? C1 C7 1.517(3) . ? C2 C3 1.392(3) . ? C2 C8 1.508(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(4) . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C10 1.385(3) . ? C9 H9A 0.9300 . ? C10 C11 1.402(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 C14 1.471(3) . ? C12 C13 1.380(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.319(4) . ? C14 H14 0.9300 . ? C15 C18 1.479(3) . ? C15 H15 0.9300 . ? C16 C17 1.375(3) . ? C16 H16 0.9300 . ? C17 C18 1.378(3) . ? C17 H17 0.9300 . ? C18 C19 1.399(4) . ? C19 C20 1.377(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 C21 C22 107.2(13) . . ? O9 C21 H21A 110.3 . . ? C22 C21 H21A 110.3 . . ? O9 C21 H21B 110.3 . . ? C22 C21 H21B 110.3 . . ? H21A C21 H21B 108.5 . . ? C21 O9 H9 109.7 . . ? O7 Zn1 O7 180.00(12) 5_655 . ? O7 Zn1 N2 90.40(7) 5_655 5_655 ? O7 Zn1 N2 89.60(7) . 5_655 ? O7 Zn1 N2 89.60(7) 5_655 . ? O7 Zn1 N2 90.40(7) . . ? N2 Zn1 N2 180.00(11) 5_655 . ? O7 Zn1 O3 88.92(6) 5_655 5_655 ? O7 Zn1 O3 91.08(6) . 5_655 ? N2 Zn1 O3 91.52(7) 5_655 5_655 ? N2 Zn1 O3 88.48(7) . 5_655 ? O7 Zn1 O3 91.08(6) 5_655 . ? O7 Zn1 O3 88.92(6) . . ? N2 Zn1 O3 88.48(7) 5_655 . ? N2 Zn1 O3 91.52(7) . . ? O3 Zn1 O3 180.00(11) 5_655 . ? O7 Zn2 O1 127.05(7) . 2_654 ? O7 Zn2 O4 106.45(7) . 5_655 ? O1 Zn2 O4 98.79(7) 2_654 5_655 ? O7 Zn2 N3 115.73(7) . 7 ? O1 Zn2 N3 100.86(7) 2_654 7 ? O4 Zn2 N3 105.02(8) 5_655 7 ? C7 O1 Zn2 115.99(15) . 2_654 ? C8 O3 Zn1 136.00(14) . . ? C8 O4 Zn2 121.81(14) . 5_655 ? Zn2 O7 Zn1 119.73(8) . . ? Zn2 O7 H7D 113.1 . . ? Zn1 O7 H7D 120.3 . . ? O5 N1 O6 122.7(3) . . ? O5 N1 C4 118.4(2) . . ? O6 N1 C4 118.9(3) . . ? C9 N2 C13 117.43(19) . . ? C9 N2 Zn1 123.78(15) . . ? C13 N2 Zn1 118.54(15) . . ? C20 N3 C16 117.0(2) . . ? C20 N3 Zn2 121.79(17) . 7 ? C16 N3 Zn2 121.21(16) . 7 ? C6 C1 C2 119.5(2) . . ? C6 C1 C7 116.9(2) . . ? C2 C1 C7 123.63(19) . . ? C3 C2 C1 119.7(2) . . ? C3 C2 C8 119.1(2) . . ? C1 C2 C8 121.07(19) . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 123.0(2) . . ? C5 C4 N1 118.1(2) . . ? C3 C4 N1 118.9(2) . . ? C6 C5 C4 117.7(2) . . ? C6 C5 H5 121.1 . . ? C4 C5 H5 121.1 . . ? C5 C6 C1 121.3(2) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O2 C7 O1 125.2(2) . . ? O2 C7 C1 119.2(2) . . ? O1 C7 C1 115.4(2) . . ? O3 C8 O4 126.2(2) . . ? O3 C8 C2 117.69(19) . . ? O4 C8 C2 116.13(19) . . ? N2 C9 C10 123.1(2) . . ? N2 C9 H9A 118.5 . . ? C10 C9 H9A 118.5 . . ? C9 C10 C11 119.5(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 116.8(2) . . ? C12 C11 C14 118.8(2) . . ? C10 C11 C14 124.4(2) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N2 C13 C12 123.1(2) . . ? N2 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C15 C14 C11 126.4(2) . . ? C15 C14 H14 116.8 . . ? C11 C14 H14 116.8 . . ? C14 C15 C18 125.4(3) . . ? C14 C15 H15 117.3 . . ? C18 C15 H15 117.3 . . ? N3 C16 C17 123.0(2) . . ? N3 C16 H16 118.5 . . ? C17 C16 H16 118.5 . . ? C16 C17 C18 120.4(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 116.5(2) . . ? C17 C18 C15 120.0(2) . . ? C19 C18 C15 123.5(2) . . ? C20 C19 C18 119.8(2) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N3 C20 C19 123.2(2) . . ? N3 C20 H20 118.4 . . ? C19 C20 H20 118.4 . . ? 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 O7 Zn1 O3 C8 -25.6(2) 5_655 . . . ? O7 Zn1 O3 C8 154.4(2) . . . . ? N2 Zn1 O3 C8 -116.0(2) 5_655 . . . ? N2 Zn1 O3 C8 64.0(2) . . . . ? O3 Zn1 O3 C8 174(100) 5_655 . . . ? O1 Zn2 O7 Zn1 -154.51(8) 2_654 . . . ? O4 Zn2 O7 Zn1 -39.52(10) 5_655 . . . ? N3 Zn2 O7 Zn1 76.74(11) 7 . . . ? O7 Zn1 O7 Zn2 153(100) 5_655 . . . ? N2 Zn1 O7 Zn2 109.86(9) 5_655 . . . ? N2 Zn1 O7 Zn2 -70.14(9) . . . . ? O3 Zn1 O7 Zn2 18.35(9) 5_655 . . . ? O3 Zn1 O7 Zn2 -161.65(9) . . . . ? O7 Zn1 N2 C9 139.01(18) 5_655 . . . ? O7 Zn1 N2 C9 -40.99(18) . . . . ? N2 Zn1 N2 C9 9(100) 5_655 . . . ? O3 Zn1 N2 C9 -132.06(18) 5_655 . . . ? O3 Zn1 N2 C9 47.94(18) . . . . ? O7 Zn1 N2 C13 -46.94(18) 5_655 . . . ? O7 Zn1 N2 C13 133.06(18) . . . . ? N2 Zn1 N2 C13 -177(100) 5_655 . . . ? O3 Zn1 N2 C13 41.99(17) 5_655 . . . ? O3 Zn1 N2 C13 -138.01(17) . . . . ? C6 C1 C2 C3 -1.1(3) . . . . ? C7 C1 C2 C3 177.6(2) . . . . ? C6 C1 C2 C8 176.6(2) . . . . ? C7 C1 C2 C8 -4.7(3) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C8 C2 C3 C4 -176.7(2) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C2 C3 C4 N1 178.6(2) . . . . ? O5 N1 C4 C5 173.0(3) . . . . ? O6 N1 C4 C5 -5.5(4) . . . . ? O5 N1 C4 C3 -5.9(4) . . . . ? O6 N1 C4 C3 175.6(3) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? N1 C4 C5 C6 -179.4(2) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C7 C1 C6 C5 -178.5(2) . . . . ? Zn2 O1 C7 O2 12.3(3) 2_654 . . . ? Zn2 O1 C7 C1 -161.74(14) 2_654 . . . ? C6 C1 C7 O2 -76.1(3) . . . . ? C2 C1 C7 O2 105.2(3) . . . . ? C6 C1 C7 O1 98.4(3) . . . . ? C2 C1 C7 O1 -80.4(3) . . . . ? Zn1 O3 C8 O4 39.7(4) . . . . ? Zn1 O3 C8 C2 -139.48(17) . . . . ? Zn2 O4 C8 O3 -2.8(3) 5_655 . . . ? Zn2 O4 C8 C2 176.32(14) 5_655 . . . ? C3 C2 C8 O3 164.7(2) . . . . ? C1 C2 C8 O3 -13.0(3) . . . . ? C3 C2 C8 O4 -14.6(3) . . . . ? C1 C2 C8 O4 167.8(2) . . . . ? C13 N2 C9 C10 0.2(3) . . . . ? Zn1 N2 C9 C10 174.34(17) . . . . ? N2 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C9 C10 C11 C14 -179.9(2) . . . . ? C10 C11 C12 C13 0.2(4) . . . . ? C14 C11 C12 C13 -179.7(2) . . . . ? C9 N2 C13 C12 0.2(4) . . . . ? Zn1 N2 C13 C12 -174.23(19) . . . . ? C11 C12 C13 N2 -0.4(4) . . . . ? C12 C11 C14 C15 176.8(3) . . . . ? C10 C11 C14 C15 -3.0(4) . . . . ? C11 C14 C15 C18 178.6(2) . . . . ? C20 N3 C16 C17 0.1(4) . . . . ? Zn2 N3 C16 C17 -179.7(2) 7 . . . ? N3 C16 C17 C18 0.3(4) . . . . ? C16 C17 C18 C19 -1.1(4) . . . . ? C16 C17 C18 C15 178.0(2) . . . . ? C14 C15 C18 C17 -173.8(3) . . . . ? C14 C15 C18 C19 5.3(4) . . . . ? C17 C18 C19 C20 1.6(4) . . . . ? C15 C18 C19 C20 -177.5(3) . . . . ? C16 N3 C20 C19 0.4(4) . . . . ? Zn2 N3 C20 C19 -179.8(2) 7 . . . ? C18 C19 C20 N3 -1.3(4) . . . . ? 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 O9 H9 O1 0.85 2.03 2.865(7) 166.3 1_565 O7 H7D O2 0.85 2.27 3.089(3) 161.8 . O8 H1W O2 0.85 1.99 2.800(3) 159.2 2_655 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.480 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 972455' ####################################################################### # # 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_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N3 O8.75 Zn1.50' _chemical_formula_weight 538.43 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.7066(13) _cell_length_b 25.077(2) _cell_length_c 13.4867(11) _cell_angle_alpha 90.00 _cell_angle_beta 124.6280(10) _cell_angle_gamma 90.00 _cell_volume 4371.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2482 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.18 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 1.716 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6097 _exptl_absorpt_correction_T_max 0.7591 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13832 _diffrn_reflns_av_R_equivalents 0.0948 _diffrn_reflns_av_sigmaI/netI 0.1118 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4056 _reflns_number_gt 2295 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+5.5711P] 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 4056 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _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 0.5000 0.0000 0.0000 0.0274(3) Uani 1 2 d S . . Zn2 Zn 0.31486(6) 0.05141(2) -0.27458(6) 0.0306(2) Uani 1 1 d . . . O1 O 0.7509(3) 0.06069(14) -0.0502(4) 0.0393(11) Uani 1 1 d . . . O2 O 0.6249(4) 0.11766(16) -0.0972(4) 0.0499(12) Uani 1 1 d . . . O3 O 0.6582(3) 0.02857(14) 0.0832(4) 0.0358(10) Uani 1 1 d . . . O4 O 0.7630(3) 0.01213(14) 0.2807(4) 0.0401(11) Uani 1 1 d . . . O5 O 0.9768(5) 0.1605(3) 0.5347(5) 0.111(2) Uani 1 1 d . . . O6 O 1.0184(5) 0.2232(2) 0.4658(5) 0.0872(19) Uani 1 1 d . . . O7 O 0.4557(3) 0.03781(13) -0.1569(3) 0.0316(10) Uani 1 1 d . . . H7D H 0.4948 0.0611 -0.1572 0.10(3) Uiso 1 1 d R . . O8 O 0.5000 0.1998(3) 0.7500 0.070(2) Uani 1 2 d S . . H1W H 0.4635 0.1796 0.6892 0.13(4) Uiso 1 1 d R . . O9 O 0.0721(7) 1.0088(3) 0.8686(8) 0.210(4) Uani 1 1 d . . . H9W H 0.0429 1.0106 0.9056 0.315 Uiso 1 1 d R . . H10W H 0.1258 0.9900 0.9137 0.315 Uiso 1 1 d R . . O10 O 0.0000 0.0000 1.0000 0.195(13) Uani 0.50 2 d SP . . H11W H 0.0556 0.0148 1.0467 0.293 Uiso 1 1 d R . . N1 N 0.9711(5) 0.1827(2) 0.4523(6) 0.0534(16) Uani 1 1 d . . . N2 N 0.4595(4) 0.07024(16) 0.0591(4) 0.0318(12) Uani 1 1 d . . . N3 N 0.2477(4) 0.38581(16) 0.2385(4) 0.0336(12) Uani 1 1 d . . . C1 C 0.7754(4) 0.1175(2) 0.1033(5) 0.0286(14) Uani 1 1 d . . . C2 C 0.7908(4) 0.0903(2) 0.2029(5) 0.0289(15) Uani 1 1 d . . . C3 C 0.8575(5) 0.1110(2) 0.3183(6) 0.0369(15) Uani 1 1 d . . . H3 H 0.8705 0.0925 0.3852 0.044 Uiso 1 1 calc R . . C4 C 0.9037(5) 0.1595(2) 0.3315(6) 0.0367(16) Uani 1 1 d . . . C5 C 0.8881(5) 0.1881(2) 0.2361(6) 0.0421(17) Uani 1 1 d . . . H5 H 0.9201 0.2209 0.2478 0.051 Uiso 1 1 calc R . . C6 C 0.8227(5) 0.1666(2) 0.1207(6) 0.0405(17) Uani 1 1 d . . . H6 H 0.8107 0.1855 0.0545 0.049 Uiso 1 1 calc R . . C7 C 0.7087(6) 0.0969(2) -0.0249(6) 0.0380(16) Uani 1 1 d . . . C8 C 0.7327(5) 0.0392(2) 0.1865(6) 0.0320(15) Uani 1 1 d . . . C9 C 0.4805(5) 0.1205(2) 0.0445(5) 0.0318(15) Uani 1 1 d . . . H9A H 0.5195 0.1255 0.0131 0.038 Uiso 1 1 calc R . . C10 C 0.4479(5) 0.1646(2) 0.0733(5) 0.0355(16) Uani 1 1 d . . . H10 H 0.4661 0.1985 0.0632 0.043 Uiso 1 1 calc R . . C11 C 0.3872(5) 0.1587(2) 0.1179(5) 0.0340(15) Uani 1 1 d . . . C12 C 0.3651(5) 0.1064(2) 0.1325(5) 0.0378(16) Uani 1 1 d . . . H12 H 0.3253 0.1003 0.1626 0.045 Uiso 1 1 calc R . . C13 C 0.4016(5) 0.0641(2) 0.1026(5) 0.0365(16) Uani 1 1 d . . . H13 H 0.3857 0.0298 0.1130 0.044 Uiso 1 1 calc R . . C14 C 0.3487(5) 0.2033(2) 0.1526(5) 0.0399(16) Uani 1 1 d . . . H14 H 0.3079 0.1947 0.1799 0.048 Uiso 1 1 calc R . . C15 C 0.3665(5) 0.2546(2) 0.1488(5) 0.0377(16) Uani 1 1 d . . . H15 H 0.4082 0.2633 0.1225 0.045 Uiso 1 1 calc R . . C16 C 0.3065(5) 0.3927(2) 0.1973(6) 0.0436(18) Uani 1 1 d . . . H16 H 0.3219 0.4274 0.1878 0.052 Uiso 1 1 calc R . . C17 C 0.3456(5) 0.3511(2) 0.1679(6) 0.0409(17) Uani 1 1 d . . . H17 H 0.3853 0.3582 0.1382 0.049 Uiso 1 1 calc R . . C18 C 0.3265(5) 0.2992(2) 0.1821(5) 0.0339(15) Uani 1 1 d . . . C19 C 0.2663(5) 0.2914(2) 0.2271(6) 0.0448(18) Uani 1 1 d . . . H19 H 0.2518 0.2571 0.2395 0.054 Uiso 1 1 calc R . . C20 C 0.2286(5) 0.3350(2) 0.2528(6) 0.0421(17) Uani 1 1 d . . . H20 H 0.1879 0.3290 0.2816 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0351(7) 0.0280(5) 0.0253(6) 0.0005(4) 0.0209(6) 0.0016(4) Zn2 0.0390(5) 0.0308(4) 0.0293(5) 0.0022(3) 0.0237(4) 0.0046(3) O1 0.050(3) 0.046(2) 0.033(3) -0.0063(19) 0.030(3) -0.001(2) O2 0.051(3) 0.044(3) 0.039(3) 0.006(2) 0.016(3) 0.004(2) O3 0.035(3) 0.047(2) 0.025(3) -0.005(2) 0.017(3) -0.011(2) O4 0.049(3) 0.039(2) 0.029(3) 0.0051(19) 0.021(3) -0.007(2) O5 0.133(6) 0.154(6) 0.043(4) -0.040(4) 0.050(4) -0.083(5) O6 0.101(5) 0.077(4) 0.067(4) -0.034(3) 0.038(4) -0.045(4) O7 0.036(3) 0.034(2) 0.031(3) 0.0071(17) 0.022(2) 0.0023(18) O8 0.061(5) 0.042(4) 0.089(6) 0.000 0.031(5) 0.000 O9 0.159(9) 0.195(8) 0.231(11) 0.072(8) 0.084(8) 0.061(7) O10 0.109(18) 0.34(3) 0.16(2) -0.19(2) 0.086(17) -0.17(2) N1 0.054(5) 0.069(4) 0.042(4) -0.022(3) 0.031(4) -0.023(3) N2 0.046(4) 0.031(3) 0.029(3) -0.001(2) 0.027(3) 0.004(2) N3 0.040(3) 0.032(3) 0.037(3) 0.001(2) 0.027(3) 0.006(2) C1 0.034(4) 0.032(3) 0.024(4) -0.003(2) 0.019(3) -0.006(3) C2 0.034(4) 0.034(3) 0.027(4) -0.005(3) 0.023(4) -0.002(3) C3 0.036(4) 0.046(4) 0.027(4) -0.006(3) 0.017(4) -0.005(3) C4 0.033(4) 0.049(4) 0.033(4) -0.017(3) 0.022(4) -0.013(3) C5 0.039(5) 0.044(4) 0.042(5) -0.014(3) 0.023(4) -0.014(3) C6 0.057(5) 0.035(3) 0.037(5) 0.000(3) 0.032(4) -0.010(3) C7 0.051(5) 0.036(3) 0.040(5) 0.005(3) 0.034(4) -0.009(3) C8 0.042(5) 0.027(3) 0.043(5) -0.004(3) 0.034(4) 0.000(3) C9 0.050(4) 0.032(3) 0.030(4) -0.005(3) 0.032(4) -0.005(3) C10 0.050(5) 0.028(3) 0.037(4) -0.002(3) 0.029(4) -0.001(3) C11 0.043(4) 0.031(3) 0.027(4) -0.002(3) 0.020(4) 0.002(3) C12 0.048(4) 0.043(3) 0.040(4) -0.006(3) 0.036(4) -0.002(3) C13 0.050(5) 0.034(3) 0.041(4) 0.001(3) 0.035(4) -0.001(3) C14 0.041(4) 0.041(4) 0.045(5) -0.002(3) 0.029(4) 0.006(3) C15 0.044(5) 0.044(4) 0.036(4) -0.002(3) 0.028(4) 0.005(3) C16 0.064(5) 0.037(3) 0.054(5) -0.001(3) 0.048(5) 0.003(3) C17 0.054(5) 0.041(4) 0.051(5) 0.001(3) 0.043(4) 0.002(3) C18 0.037(4) 0.033(3) 0.032(4) 0.002(3) 0.020(4) 0.010(3) C19 0.059(5) 0.034(3) 0.055(5) -0.005(3) 0.040(4) 0.001(3) C20 0.047(5) 0.042(4) 0.051(5) -0.002(3) 0.036(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 O7 2.047(4) . ? Zn1 O7 2.047(4) 5_655 ? Zn1 N2 2.173(4) 5_655 ? Zn1 N2 2.173(4) . ? Zn1 O3 2.186(4) 5_655 ? Zn1 O3 2.186(4) . ? Zn2 O7 1.881(4) . ? Zn2 O4 1.981(4) 5_655 ? Zn2 O1 1.983(4) 2_654 ? Zn2 N3 2.055(4) 7 ? O1 C7 1.279(7) . ? O1 Zn2 1.983(4) 2_654 ? O2 C7 1.223(7) . ? O3 C8 1.236(7) . ? O4 C8 1.271(7) . ? O4 Zn2 1.981(4) 5_655 ? O5 N1 1.199(7) . ? O6 N1 1.211(6) . ? O7 H7D 0.8499 . ? O8 H1W 0.8501 . ? O9 H9W 0.8500 . ? O9 H10W 0.8501 . ? O10 H11W 0.8197 . ? N1 C4 1.467(8) . ? N2 C13 1.341(6) . ? N2 C9 1.346(6) . ? N3 C16 1.333(7) . ? N3 C20 1.347(6) . ? N3 Zn2 2.055(4) 7 ? C1 C6 1.389(7) . ? C1 C2 1.400(7) . ? C1 C7 1.515(8) . ? C2 C3 1.391(7) . ? C2 C8 1.514(7) . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C4 C5 1.368(8) . ? C5 C6 1.397(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C10 1.365(7) . ? C9 H9A 0.9300 . ? C10 C11 1.394(8) . ? C10 H10 0.9300 . ? C11 C12 1.398(7) . ? C11 C14 1.468(7) . ? C12 C13 1.371(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.323(7) . ? C14 H14 0.9300 . ? C15 C18 1.474(7) . ? C15 H15 0.9300 . ? C16 C17 1.379(7) . ? C16 H16 0.9300 . ? C17 C18 1.372(7) . ? C17 H17 0.9300 . ? C18 C19 1.396(8) . ? C19 C20 1.379(7) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Zn1 O7 180.0(2) . 5_655 ? O7 Zn1 N2 89.68(15) . 5_655 ? O7 Zn1 N2 90.32(15) 5_655 5_655 ? O7 Zn1 N2 90.32(15) . . ? O7 Zn1 N2 89.68(15) 5_655 . ? N2 Zn1 N2 180.0(3) 5_655 . ? O7 Zn1 O3 90.09(15) . 5_655 ? O7 Zn1 O3 89.91(15) 5_655 5_655 ? N2 Zn1 O3 91.76(16) 5_655 5_655 ? N2 Zn1 O3 88.24(16) . 5_655 ? O7 Zn1 O3 89.91(15) . . ? O7 Zn1 O3 90.09(15) 5_655 . ? N2 Zn1 O3 88.24(16) 5_655 . ? N2 Zn1 O3 91.76(16) . . ? O3 Zn1 O3 180.0(2) 5_655 . ? O7 Zn2 O4 106.94(16) . 5_655 ? O7 Zn2 O1 126.39(16) . 2_654 ? O4 Zn2 O1 98.83(16) 5_655 2_654 ? O7 Zn2 N3 115.49(17) . 7 ? O4 Zn2 N3 105.03(18) 5_655 7 ? O1 Zn2 N3 101.34(17) 2_654 7 ? C7 O1 Zn2 113.8(4) . 2_654 ? C8 O3 Zn1 136.1(4) . . ? C8 O4 Zn2 121.1(4) . 5_655 ? Zn2 O7 Zn1 120.16(19) . . ? Zn2 O7 H7D 112.2 . . ? Zn1 O7 H7D 120.1 . . ? H9W O9 H10W 104.9 . . ? O5 N1 O6 122.1(6) . . ? O5 N1 C4 118.3(6) . . ? O6 N1 C4 119.6(6) . . ? C13 N2 C9 117.1(4) . . ? C13 N2 Zn1 118.7(3) . . ? C9 N2 Zn1 123.9(4) . . ? C16 N3 C20 116.5(5) . . ? C16 N3 Zn2 122.5(4) . 7 ? C20 N3 Zn2 121.1(4) . 7 ? C6 C1 C2 119.1(5) . . ? C6 C1 C7 116.9(5) . . ? C2 C1 C7 124.0(5) . . ? C3 C2 C1 120.1(5) . . ? C3 C2 C8 119.2(5) . . ? C1 C2 C8 120.7(5) . . ? C4 C3 C2 118.8(6) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 122.9(6) . . ? C5 C4 N1 117.8(5) . . ? C3 C4 N1 119.3(6) . . ? C4 C5 C6 118.1(5) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 121.0(5) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O2 C7 O1 125.1(6) . . ? O2 C7 C1 119.8(6) . . ? O1 C7 C1 114.8(6) . . ? O3 C8 O4 126.0(5) . . ? O3 C8 C2 117.0(5) . . ? O4 C8 C2 117.0(6) . . ? N2 C9 C10 123.7(5) . . ? N2 C9 H9A 118.2 . . ? C10 C9 H9A 118.2 . . ? C9 C10 C11 119.7(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 116.5(5) . . ? C10 C11 C14 124.2(5) . . ? C12 C11 C14 119.3(5) . . ? C13 C12 C11 120.3(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? N2 C13 C12 122.7(5) . . ? N2 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C15 C14 C11 126.5(6) . . ? C15 C14 H14 116.8 . . ? C11 C14 H14 116.8 . . ? C14 C15 C18 126.2(6) . . ? C14 C15 H15 116.9 . . ? C18 C15 H15 116.9 . . ? N3 C16 C17 123.2(5) . . ? N3 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 120.6(5) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 116.7(5) . . ? C17 C18 C15 120.8(5) . . ? C19 C18 C15 122.5(5) . . ? C20 C19 C18 119.4(5) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? N3 C20 C19 123.5(6) . . ? N3 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? 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 O7 Zn1 O3 C8 152.4(5) . . . . ? O7 Zn1 O3 C8 -27.6(5) 5_655 . . . ? N2 Zn1 O3 C8 -117.9(5) 5_655 . . . ? N2 Zn1 O3 C8 62.1(5) . . . . ? O3 Zn1 O3 C8 -8(100) 5_655 . . . ? O4 Zn2 O7 Zn1 -39.7(2) 5_655 . . . ? O1 Zn2 O7 Zn1 -154.75(17) 2_654 . . . ? N3 Zn2 O7 Zn1 76.8(2) 7 . . . ? O7 Zn1 O7 Zn2 -17(56) 5_655 . . . ? N2 Zn1 O7 Zn2 109.6(2) 5_655 . . . ? N2 Zn1 O7 Zn2 -70.4(2) . . . . ? O3 Zn1 O7 Zn2 17.8(2) 5_655 . . . ? O3 Zn1 O7 Zn2 -162.2(2) . . . . ? O7 Zn1 N2 C13 131.9(4) . . . . ? O7 Zn1 N2 C13 -48.1(4) 5_655 . . . ? N2 Zn1 N2 C13 10(63) 5_655 . . . ? O3 Zn1 N2 C13 41.8(4) 5_655 . . . ? O3 Zn1 N2 C13 -138.2(4) . . . . ? O7 Zn1 N2 C9 -41.6(5) . . . . ? O7 Zn1 N2 C9 138.4(5) 5_655 . . . ? N2 Zn1 N2 C9 -164(63) 5_655 . . . ? O3 Zn1 N2 C9 -131.7(5) 5_655 . . . ? O3 Zn1 N2 C9 48.3(5) . . . . ? C6 C1 C2 C3 -3.7(8) . . . . ? C7 C1 C2 C3 176.8(5) . . . . ? C6 C1 C2 C8 174.1(5) . . . . ? C7 C1 C2 C8 -5.4(8) . . . . ? C1 C2 C3 C4 2.9(8) . . . . ? C8 C2 C3 C4 -175.0(5) . . . . ? C2 C3 C4 C5 -0.7(9) . . . . ? C2 C3 C4 N1 177.7(5) . . . . ? O5 N1 C4 C5 172.5(7) . . . . ? O6 N1 C4 C5 -7.2(9) . . . . ? O5 N1 C4 C3 -6.0(9) . . . . ? O6 N1 C4 C3 174.3(6) . . . . ? C3 C4 C5 C6 -0.5(9) . . . . ? N1 C4 C5 C6 -178.9(5) . . . . ? C2 C1 C6 C5 2.4(9) . . . . ? C7 C1 C6 C5 -178.0(6) . . . . ? C4 C5 C6 C1 -0.4(9) . . . . ? Zn2 O1 C7 O2 13.4(7) 2_654 . . . ? Zn2 O1 C7 C1 -160.9(3) 2_654 . . . ? C6 C1 C7 O2 -72.0(7) . . . . ? C2 C1 C7 O2 107.5(7) . . . . ? C6 C1 C7 O1 102.6(6) . . . . ? C2 C1 C7 O1 -77.9(7) . . . . ? Zn1 O3 C8 O4 42.2(8) . . . . ? Zn1 O3 C8 C2 -135.5(4) . . . . ? Zn2 O4 C8 O3 -4.1(8) 5_655 . . . ? Zn2 O4 C8 C2 173.6(3) 5_655 . . . ? C3 C2 C8 O3 164.2(5) . . . . ? C1 C2 C8 O3 -13.6(8) . . . . ? C3 C2 C8 O4 -13.7(8) . . . . ? C1 C2 C8 O4 168.4(5) . . . . ? C13 N2 C9 C10 1.1(9) . . . . ? Zn1 N2 C9 C10 174.7(5) . . . . ? N2 C9 C10 C11 -1.6(10) . . . . ? C9 C10 C11 C12 1.2(9) . . . . ? C9 C10 C11 C14 179.4(6) . . . . ? C10 C11 C12 C13 -0.6(9) . . . . ? C14 C11 C12 C13 -178.9(6) . . . . ? C9 N2 C13 C12 -0.4(9) . . . . ? Zn1 N2 C13 C12 -174.3(5) . . . . ? C11 C12 C13 N2 0.2(10) . . . . ? C10 C11 C14 C15 -1.0(10) . . . . ? C12 C11 C14 C15 177.1(6) . . . . ? C11 C14 C15 C18 179.1(6) . . . . ? C20 N3 C16 C17 1.1(9) . . . . ? Zn2 N3 C16 C17 -177.3(5) 7 . . . ? N3 C16 C17 C18 -1.1(10) . . . . ? C16 C17 C18 C19 0.0(10) . . . . ? C16 C17 C18 C15 178.9(6) . . . . ? C14 C15 C18 C17 -176.3(6) . . . . ? C14 C15 C18 C19 2.5(10) . . . . ? C17 C18 C19 C20 0.9(10) . . . . ? C15 C18 C19 C20 -177.9(6) . . . . ? C16 N3 C20 C19 -0.1(9) . . . . ? Zn2 N3 C20 C19 178.3(5) 7 . . . ? C18 C19 C20 N3 -0.9(10) . . . . ? 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 O10 H11W O4 0.82 2.45 3.192(4) 150.8 2_656 O9 H10W O1 0.85 2.17 3.005(9) 168.0 5_666 O9 H9W O10 0.85 1.77 2.598(10) 165.8 1_565 O8 H1W O2 0.85 1.98 2.783(6) 157.0 2_655 O7 H7D O2 0.85 2.23 3.048(6) 162.3 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.488 _refine_diff_density_min -0.963 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 972456' ####################################################################### # # 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_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N3 O7.50 Zn1.50' _chemical_formula_weight 515.41 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.307(3) _cell_length_b 25.365(4) _cell_length_c 13.442(2) _cell_angle_alpha 90.00 _cell_angle_beta 124.029(2) _cell_angle_gamma 90.00 _cell_volume 4325.2(13) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4646 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.13 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 1.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6081 _exptl_absorpt_correction_T_max 0.7579 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11937 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4003 _reflns_number_gt 3362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+2.3340P] 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 4003 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.5000 0.0000 0.0000 0.02371(10) Uani 1 2 d S . . Zn2 Zn 0.31094(2) 0.051222(9) -0.27296(2) 0.02700(9) Uani 1 1 d . . . O1 O 0.75537(13) 0.06243(6) -0.05309(13) 0.0379(4) Uani 1 1 d . . . O2 O 0.62493(14) 0.11734(7) -0.09870(14) 0.0457(4) Uani 1 1 d . . . O3 O 0.66079(12) 0.02727(6) 0.08024(13) 0.0334(4) Uani 1 1 d . . . O4 O 0.76966(13) 0.01055(6) 0.27641(13) 0.0416(4) Uani 1 1 d . . . O5 O 0.9903(2) 0.15326(11) 0.53417(18) 0.0989(10) Uani 1 1 d . . . O6 O 1.0094(2) 0.22356(9) 0.4622(2) 0.0892(8) Uani 1 1 d . . . O7 O 0.45448(12) 0.03665(6) -0.15696(12) 0.0296(3) Uani 1 1 d . . . H7D H 0.4932 0.0597 -0.1573 0.062(10) Uiso 1 1 d R . . O8 O 0.5000 0.19971(10) 0.7500 0.0645(8) Uani 1 2 d S . . H1W H 0.4636 0.1796 0.6895 0.135(18) Uiso 1 1 d R . . N1 N 0.97320(18) 0.18006(10) 0.4506(2) 0.0513(6) Uani 1 1 d . . . N2 N 0.46009(14) 0.06977(7) 0.05965(15) 0.0282(4) Uani 1 1 d . . . N3 N 0.24952(15) 0.38558(7) 0.23377(16) 0.0306(4) Uani 1 1 d . . . C1 C 0.77680(17) 0.11712(8) 0.10077(18) 0.0278(5) Uani 1 1 d . . . C2 C 0.79492(17) 0.08842(8) 0.19968(18) 0.0267(5) Uani 1 1 d . . . C3 C 0.86172(17) 0.10883(9) 0.31466(19) 0.0321(5) Uani 1 1 d . . . H3 H 0.8772 0.0894 0.3813 0.038 Uiso 1 1 calc R . . C4 C 0.90475(18) 0.15821(9) 0.3285(2) 0.0350(5) Uani 1 1 d . . . C5 C 0.88582(19) 0.18810(9) 0.2329(2) 0.0383(6) Uani 1 1 d . . . H5 H 0.9152 0.2215 0.2447 0.046 Uiso 1 1 calc R . . C6 C 0.82173(19) 0.16703(9) 0.1187(2) 0.0368(6) Uani 1 1 d . . . H6 H 0.8084 0.1865 0.0529 0.044 Uiso 1 1 calc R . . C7 C 0.71101(19) 0.09692(9) -0.02728(19) 0.0307(5) Uani 1 1 d . . . C8 C 0.73692(18) 0.03775(8) 0.18270(19) 0.0277(5) Uani 1 1 d . . . C9 C 0.48275(18) 0.11869(8) 0.04417(18) 0.0300(5) Uani 1 1 d . . . H9A H 0.5230 0.1229 0.0126 0.036 Uiso 1 1 calc R . . C10 C 0.44966(18) 0.16332(8) 0.07253(19) 0.0317(5) Uani 1 1 d . . . H10 H 0.4683 0.1965 0.0610 0.038 Uiso 1 1 calc R . . C11 C 0.38791(18) 0.15821(9) 0.11870(18) 0.0304(5) Uani 1 1 d . . . C12 C 0.36413(19) 0.10714(9) 0.1338(2) 0.0343(5) Uani 1 1 d . . . H12 H 0.3231 0.1017 0.1640 0.041 Uiso 1 1 calc R . . C13 C 0.40126(18) 0.06466(8) 0.10420(19) 0.0320(5) Uani 1 1 d . . . H13 H 0.3847 0.0309 0.1157 0.038 Uiso 1 1 calc R . . C14 C 0.34870(19) 0.20319(9) 0.1518(2) 0.0358(5) Uani 1 1 d . . . H14 H 0.3063 0.1955 0.1793 0.043 Uiso 1 1 calc R . . C15 C 0.36796(18) 0.25370(9) 0.14608(19) 0.0338(5) Uani 1 1 d . . . H15 H 0.4107 0.2615 0.1190 0.041 Uiso 1 1 calc R . . C16 C 0.30983(19) 0.39138(9) 0.1920(2) 0.0370(6) Uani 1 1 d . . . H16 H 0.3262 0.4254 0.1816 0.044 Uiso 1 1 calc R . . C17 C 0.34935(19) 0.34953(9) 0.1634(2) 0.0366(6) Uani 1 1 d . . . H17 H 0.3906 0.3557 0.1338 0.044 Uiso 1 1 calc R . . C18 C 0.32776(18) 0.29836(9) 0.17872(18) 0.0306(5) Uani 1 1 d . . . C19 C 0.2665(2) 0.29253(9) 0.2246(2) 0.0411(6) Uani 1 1 d . . . H19 H 0.2509 0.2590 0.2384 0.049 Uiso 1 1 calc R . . C20 C 0.2291(2) 0.33596(9) 0.2496(2) 0.0393(6) Uani 1 1 d . . . H20 H 0.1873 0.3309 0.2790 0.047 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 0.0322(2) 0.01932(17) 0.02107(17) -0.00020(13) 0.01576(16) 0.00068(14) Zn2 0.03692(17) 0.02252(14) 0.02381(13) 0.00247(10) 0.01837(12) 0.00453(11) O1 0.0484(11) 0.0421(9) 0.0263(8) -0.0080(7) 0.0229(8) -0.0047(8) O2 0.0483(11) 0.0439(10) 0.0310(9) 0.0057(8) 0.0135(9) 0.0018(8) O3 0.0377(10) 0.0365(9) 0.0262(8) -0.0043(7) 0.0179(7) -0.0133(7) O4 0.0483(11) 0.0374(9) 0.0297(8) 0.0073(7) 0.0161(8) -0.0092(8) O5 0.121(2) 0.131(2) 0.0356(11) -0.0293(13) 0.0378(13) -0.0706(18) O6 0.111(2) 0.0604(15) 0.0642(14) -0.0370(12) 0.0294(14) -0.0371(14) O7 0.0344(9) 0.0288(8) 0.0269(8) 0.0052(6) 0.0181(7) 0.0017(7) O8 0.0643(19) 0.0320(14) 0.080(2) 0.000 0.0300(17) 0.000 N1 0.0505(15) 0.0622(16) 0.0423(13) -0.0252(12) 0.0266(12) -0.0190(12) N2 0.0372(11) 0.0233(9) 0.0265(9) -0.0007(7) 0.0193(9) 0.0024(8) N3 0.0370(11) 0.0265(10) 0.0313(10) 0.0002(8) 0.0210(9) 0.0044(8) C1 0.0343(13) 0.0253(11) 0.0278(11) -0.0038(9) 0.0199(10) -0.0035(9) C2 0.0304(12) 0.0269(11) 0.0258(11) -0.0033(9) 0.0174(10) -0.0020(9) C3 0.0358(14) 0.0382(13) 0.0251(11) -0.0029(10) 0.0188(10) -0.0042(10) C4 0.0349(14) 0.0402(14) 0.0320(12) -0.0159(10) 0.0199(11) -0.0091(11) C5 0.0436(15) 0.0283(12) 0.0482(14) -0.0128(11) 0.0289(13) -0.0120(11) C6 0.0479(15) 0.0292(12) 0.0360(12) -0.0019(10) 0.0253(12) -0.0076(11) C7 0.0418(15) 0.0278(12) 0.0258(11) -0.0021(9) 0.0209(11) -0.0119(10) C8 0.0344(13) 0.0246(11) 0.0294(11) -0.0004(9) 0.0212(11) 0.0001(9) C9 0.0398(14) 0.0268(11) 0.0289(11) 0.0008(9) 0.0225(11) 0.0005(10) C10 0.0454(14) 0.0208(11) 0.0327(12) -0.0009(9) 0.0242(11) -0.0013(10) C11 0.0339(13) 0.0287(12) 0.0265(11) -0.0041(9) 0.0156(10) 0.0034(10) C12 0.0424(15) 0.0320(12) 0.0382(12) -0.0013(10) 0.0286(12) 0.0019(11) C13 0.0438(15) 0.0243(11) 0.0350(12) -0.0003(9) 0.0263(12) -0.0019(10) C14 0.0406(15) 0.0347(13) 0.0374(13) -0.0028(10) 0.0250(12) 0.0064(11) C15 0.0394(14) 0.0320(13) 0.0339(12) -0.0011(10) 0.0229(11) 0.0072(11) C16 0.0496(16) 0.0257(12) 0.0433(13) 0.0001(10) 0.0305(13) 0.0023(11) C17 0.0448(15) 0.0328(13) 0.0432(13) -0.0003(10) 0.0313(12) 0.0032(11) C18 0.0347(14) 0.0296(12) 0.0265(11) -0.0016(9) 0.0165(10) 0.0048(10) C19 0.0571(17) 0.0235(12) 0.0557(15) -0.0017(11) 0.0396(14) 0.0012(11) C20 0.0505(16) 0.0311(13) 0.0507(14) 0.0001(11) 0.0371(13) 0.0029(11) _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 O7 2.0386(14) . ? Zn1 O7 2.0386(14) 5_655 ? Zn1 N2 2.1671(17) . ? Zn1 N2 2.1671(17) 5_655 ? Zn1 O3 2.1745(15) . ? Zn1 O3 2.1745(15) 5_655 ? Zn2 O7 1.8871(15) . ? Zn2 O4 1.9786(16) 5_655 ? Zn2 O1 1.9804(15) 2_654 ? Zn2 N3 2.0613(18) 7 ? O1 C7 1.269(3) . ? O1 Zn2 1.9804(15) 2_654 ? O2 C7 1.229(3) . ? O3 C8 1.237(2) . ? O4 C8 1.268(2) . ? O4 Zn2 1.9786(16) 5_655 ? O5 N1 1.210(3) . ? O6 N1 1.205(3) . ? O7 H7D 0.8330 . ? O8 H1W 0.8510 . ? N1 C4 1.474(3) . ? N2 C9 1.336(3) . ? N2 C13 1.338(3) . ? N3 C16 1.330(3) . ? N3 C20 1.342(3) . ? N3 Zn2 2.0613(18) 7 ? C1 C6 1.396(3) . ? C1 C2 1.401(3) . ? C1 C7 1.516(3) . ? C2 C3 1.391(3) . ? C2 C8 1.505(3) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C10 1.378(3) . ? C9 H9A 0.9300 . ? C10 C11 1.397(3) . ? C10 H10 0.9300 . ? C11 C12 1.391(3) . ? C11 C14 1.469(3) . ? C12 C13 1.377(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.326(3) . ? C14 H14 0.9300 . ? C15 C18 1.469(3) . ? C15 H15 0.9300 . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.388(3) . ? C19 C20 1.368(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Zn1 O7 180.00(11) . 5_655 ? O7 Zn1 N2 90.38(6) . . ? O7 Zn1 N2 89.62(6) 5_655 . ? O7 Zn1 N2 89.62(6) . 5_655 ? O7 Zn1 N2 90.38(6) 5_655 5_655 ? N2 Zn1 N2 180.00(10) . 5_655 ? O7 Zn1 O3 90.27(6) . . ? O7 Zn1 O3 89.73(6) 5_655 . ? N2 Zn1 O3 91.82(6) . . ? N2 Zn1 O3 88.18(6) 5_655 . ? O7 Zn1 O3 89.73(6) . 5_655 ? O7 Zn1 O3 90.27(6) 5_655 5_655 ? N2 Zn1 O3 88.18(6) . 5_655 ? N2 Zn1 O3 91.82(6) 5_655 5_655 ? O3 Zn1 O3 180.00(9) . 5_655 ? O7 Zn2 O4 106.66(7) . 5_655 ? O7 Zn2 O1 126.45(7) . 2_654 ? O4 Zn2 O1 100.67(6) 5_655 2_654 ? O7 Zn2 N3 115.01(7) . 7 ? O4 Zn2 N3 104.98(8) 5_655 7 ? O1 Zn2 N3 100.57(7) 2_654 7 ? C7 O1 Zn2 115.00(14) . 2_654 ? C8 O3 Zn1 136.09(14) . . ? C8 O4 Zn2 120.86(14) . 5_655 ? Zn2 O7 Zn1 120.67(8) . . ? Zn2 O7 H7D 111.2 . . ? Zn1 O7 H7D 119.5 . . ? O6 N1 O5 123.3(2) . . ? O6 N1 C4 118.5(2) . . ? O5 N1 C4 118.2(2) . . ? C9 N2 C13 117.27(19) . . ? C9 N2 Zn1 123.33(14) . . ? C13 N2 Zn1 119.09(14) . . ? C16 N3 C20 116.67(19) . . ? C16 N3 Zn2 122.60(15) . 7 ? C20 N3 Zn2 120.72(15) . 7 ? C6 C1 C2 119.38(19) . . ? C6 C1 C7 116.92(19) . . ? C2 C1 C7 123.70(18) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 C8 119.40(19) . . ? C1 C2 C8 120.88(18) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 122.6(2) . . ? C5 C4 N1 118.6(2) . . ? C3 C4 N1 118.7(2) . . ? C4 C5 C6 118.1(2) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 121.1(2) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O2 C7 O1 125.5(2) . . ? O2 C7 C1 119.0(2) . . ? O1 C7 C1 115.2(2) . . ? O3 C8 O4 126.3(2) . . ? O3 C8 C2 117.43(18) . . ? O4 C8 C2 116.25(19) . . ? N2 C9 C10 123.5(2) . . ? N2 C9 H9A 118.2 . . ? C10 C9 H9A 118.2 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 116.66(19) . . ? C12 C11 C14 119.6(2) . . ? C10 C11 C14 123.7(2) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N2 C13 C12 123.0(2) . . ? N2 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C15 C14 C11 126.2(2) . . ? C15 C14 H14 116.9 . . ? C11 C14 H14 116.9 . . ? C14 C15 C18 125.7(2) . . ? C14 C15 H15 117.1 . . ? C18 C15 H15 117.1 . . ? N3 C16 C17 123.3(2) . . ? N3 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C16 C17 C18 120.2(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C19 116.3(2) . . ? C17 C18 C15 120.3(2) . . ? C19 C18 C15 123.4(2) . . ? C20 C19 C18 120.2(2) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? N3 C20 C19 123.3(2) . . ? N3 C20 H20 118.3 . . ? C19 C20 H20 118.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O7 Zn1 O3 C8 152.4(2) . . . . ? O7 Zn1 O3 C8 -27.6(2) 5_655 . . . ? N2 Zn1 O3 C8 62.0(2) . . . . ? N2 Zn1 O3 C8 -118.0(2) 5_655 . . . ? O3 Zn1 O3 C8 4(100) 5_655 . . . ? O4 Zn2 O7 Zn1 -39.53(10) 5_655 . . . ? O1 Zn2 O7 Zn1 -157.00(7) 2_654 . . . ? N3 Zn2 O7 Zn1 76.41(10) 7 . . . ? O7 Zn1 O7 Zn2 180(57) 5_655 . . . ? N2 Zn1 O7 Zn2 -69.83(9) . . . . ? N2 Zn1 O7 Zn2 110.17(9) 5_655 . . . ? O3 Zn1 O7 Zn2 -161.66(9) . . . . ? O3 Zn1 O7 Zn2 18.34(9) 5_655 . . . ? O7 Zn1 N2 C9 -42.05(17) . . . . ? O7 Zn1 N2 C9 137.95(17) 5_655 . . . ? N2 Zn1 N2 C9 67(100) 5_655 . . . ? O3 Zn1 N2 C9 48.23(17) . . . . ? O3 Zn1 N2 C9 -131.77(17) 5_655 . . . ? O7 Zn1 N2 C13 131.44(16) . . . . ? O7 Zn1 N2 C13 -48.56(16) 5_655 . . . ? N2 Zn1 N2 C13 -119(100) 5_655 . . . ? O3 Zn1 N2 C13 -138.28(16) . . . . ? O3 Zn1 N2 C13 41.72(16) 5_655 . . . ? C6 C1 C2 C3 -3.4(3) . . . . ? C7 C1 C2 C3 176.0(2) . . . . ? C6 C1 C2 C8 172.1(2) . . . . ? C7 C1 C2 C8 -8.6(3) . . . . ? C1 C2 C3 C4 3.2(3) . . . . ? C8 C2 C3 C4 -172.3(2) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C2 C3 C4 N1 178.4(2) . . . . ? O6 N1 C4 C5 0.7(4) . . . . ? O5 N1 C4 C5 -179.2(3) . . . . ? O6 N1 C4 C3 -178.9(3) . . . . ? O5 N1 C4 C3 1.2(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? N1 C4 C5 C6 179.7(2) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? C7 C1 C6 C5 -177.9(2) . . . . ? Zn2 O1 C7 O2 11.0(3) 2_654 . . . ? Zn2 O1 C7 C1 -163.13(13) 2_654 . . . ? C6 C1 C7 O2 -70.7(3) . . . . ? C2 C1 C7 O2 109.9(3) . . . . ? C6 C1 C7 O1 103.8(2) . . . . ? C2 C1 C7 O1 -75.6(3) . . . . ? Zn1 O3 C8 O4 44.6(3) . . . . ? Zn1 O3 C8 C2 -133.40(17) . . . . ? Zn2 O4 C8 O3 -7.2(3) 5_655 . . . ? Zn2 O4 C8 C2 170.81(14) 5_655 . . . ? C3 C2 C8 O3 163.2(2) . . . . ? C1 C2 C8 O3 -12.2(3) . . . . ? C3 C2 C8 O4 -15.0(3) . . . . ? C1 C2 C8 O4 169.6(2) . . . . ? C13 N2 C9 C10 0.6(3) . . . . ? Zn1 N2 C9 C10 174.20(16) . . . . ? N2 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C9 C10 C11 C14 180.0(2) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? C14 C11 C12 C13 -179.4(2) . . . . ? C9 N2 C13 C12 0.0(3) . . . . ? Zn1 N2 C13 C12 -173.84(17) . . . . ? C11 C12 C13 N2 -0.4(4) . . . . ? C12 C11 C14 C15 177.6(2) . . . . ? C10 C11 C14 C15 -2.0(4) . . . . ? C11 C14 C15 C18 179.6(2) . . . . ? C20 N3 C16 C17 1.1(3) . . . . ? Zn2 N3 C16 C17 -178.84(18) 7 . . . ? N3 C16 C17 C18 -0.6(4) . . . . ? C16 C17 C18 C19 -0.7(3) . . . . ? C16 C17 C18 C15 178.8(2) . . . . ? C14 C15 C18 C17 -176.9(2) . . . . ? C14 C15 C18 C19 2.5(4) . . . . ? C17 C18 C19 C20 1.4(4) . . . . ? C15 C18 C19 C20 -178.0(2) . . . . ? C16 N3 C20 C19 -0.3(4) . . . . ? Zn2 N3 C20 C19 179.66(19) 7 . . . ? C18 C19 C20 N3 -1.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H1W O2 0.85 1.99 2.794(3) 156.5 2_655 O7 H7D O2 0.83 2.25 3.053(2) 162.8 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.304 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 972457' ####################################################################### # # 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_d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 I N3 O7.50 Zn1.50' _chemical_formula_weight 642.31 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.291(7) _cell_length_b 24.684(11) _cell_length_c 13.435(6) _cell_angle_alpha 90.00 _cell_angle_beta 124.098(5) _cell_angle_gamma 90.00 _cell_volume 4474(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3705 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 23.76 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2512 _exptl_absorpt_coefficient_mu 3.051 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4418 _exptl_absorpt_correction_T_max 0.6250 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16323 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4156 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+48.9847P] 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 4156 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1752 _refine_ls_wR_factor_gt 0.1581 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 I1 I 0.5331(6) 0.4980(3) 0.3619(9) 0.369(9) Uani 0.436(9) 1 d P . 1 I2 I 0.4342(2) 0.50296(10) 0.1333(2) 0.0934(11) Uani 0.564(9) 1 d P . 2 Zn1 Zn 0.0000 0.5000 0.0000 0.0257(3) Uani 1 2 d S . . Zn2 Zn -0.17491(6) 0.55238(3) -0.27097(7) 0.0293(2) Uani 1 1 d . . . O1 O 0.2361(4) 0.5634(2) -0.0564(4) 0.0441(13) Uani 1 1 d . . . O2 O 0.1200(4) 0.6223(2) -0.0895(5) 0.0557(15) Uani 1 1 d . . . O3 O 0.1509(4) 0.5298(2) 0.0835(4) 0.0365(11) Uani 1 1 d . . . O4 O 0.2508(4) 0.5129(2) 0.2803(5) 0.0431(13) Uani 1 1 d . . . O5 O 0.4690(7) 0.6568(4) 0.5361(7) 0.114(3) Uani 1 1 d . . . O6 O 0.5180(6) 0.7164(3) 0.4703(7) 0.099(3) Uani 1 1 d . . . O7 O -0.0402(3) 0.53897(18) -0.1544(4) 0.0315(10) Uani 1 1 d . . . H7D H -0.0015 0.5620 -0.1547 0.04(2) Uiso 1 1 d R . . O8 O 0.5000 0.2032(4) 0.7500 0.075(3) Uani 1 2 d S . . H1W H 0.4636 0.1831 0.6895 0.07(3) Uiso 1 1 d R . . N1 N 0.4681(6) 0.6778(3) 0.4550(6) 0.0558(19) Uani 1 1 d . . . N2 N -0.0403(4) 0.5710(2) 0.0592(5) 0.0325(13) Uani 1 1 d . . . N3 N -0.2628(4) 0.8844(2) 0.2356(5) 0.0357(14) Uani 1 1 d . . . C1 C 0.2683(5) 0.6180(3) 0.1042(6) 0.0309(15) Uani 1 1 d . . . C2 C 0.2815(5) 0.5903(3) 0.2035(6) 0.0286(14) Uani 1 1 d . . . C3 C 0.3490(5) 0.6096(3) 0.3183(6) 0.0361(16) Uani 1 1 d . . . H3 H 0.3598 0.5908 0.3846 0.043 Uiso 1 1 calc R . . C4 C 0.4001(6) 0.6567(3) 0.3343(7) 0.0387(17) Uani 1 1 d . . . C5 C 0.3885(6) 0.6854(3) 0.2393(7) 0.0450(19) Uani 1 1 d . . . H5 H 0.4245 0.7168 0.2520 0.054 Uiso 1 1 calc R . . C6 C 0.3213(6) 0.6659(3) 0.1241(7) 0.0425(18) Uani 1 1 d . . . H6 H 0.3113 0.6852 0.0586 0.051 Uiso 1 1 calc R . . C7 C 0.2005(6) 0.5997(3) -0.0234(6) 0.0359(17) Uani 1 1 d . . . C8 C 0.2215(5) 0.5404(3) 0.1854(6) 0.0302(15) Uani 1 1 d . . . C9 C -0.0207(6) 0.6216(3) 0.0459(6) 0.0347(16) Uani 1 1 d . . . H9A H 0.0180 0.6270 0.0158 0.042 Uiso 1 1 calc R . . C10 C -0.0540(6) 0.6663(3) 0.0736(7) 0.0384(17) Uani 1 1 d . . . H10 H -0.0384 0.7010 0.0620 0.046 Uiso 1 1 calc R . . C11 C -0.1125(6) 0.6590(3) 0.1200(6) 0.0373(17) Uani 1 1 d . . . C12 C -0.1327(6) 0.6057(3) 0.1333(7) 0.0396(17) Uani 1 1 d . . . H12 H -0.1710 0.5987 0.1634 0.047 Uiso 1 1 calc R . . C13 C -0.0969(6) 0.5636(3) 0.1028(7) 0.0377(17) Uani 1 1 d . . . H13 H -0.1119 0.5284 0.1123 0.045 Uiso 1 1 calc R . . C14 C -0.1512(6) 0.7033(3) 0.1547(7) 0.0432(18) Uani 1 1 d . . . H14 H -0.1910 0.6935 0.1812 0.052 Uiso 1 1 calc R . . C15 C -0.1361(6) 0.7552(3) 0.1523(7) 0.0428(18) Uani 1 1 d . . . H15 H -0.0945 0.7653 0.1286 0.051 Uiso 1 1 calc R . . C16 C -0.2054(6) 0.8930(3) 0.1959(7) 0.0453(19) Uani 1 1 d . . . H16 H -0.1929 0.9286 0.1858 0.054 Uiso 1 1 calc R . . C17 C -0.1634(6) 0.8523(3) 0.1690(8) 0.048(2) Uani 1 1 d . . . H17 H -0.1245 0.8608 0.1405 0.057 Uiso 1 1 calc R . . C18 C -0.1788(5) 0.7992(3) 0.1840(6) 0.0362(16) Uani 1 1 d . . . C19 C -0.2373(7) 0.7896(3) 0.2280(8) 0.050(2) Uani 1 1 d . . . H19 H -0.2489 0.7544 0.2417 0.060 Uiso 1 1 calc R . . C20 C -0.2777(6) 0.8329(3) 0.2509(8) 0.048(2) Uani 1 1 d . . . H20 H -0.3177 0.8257 0.2786 0.057 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 I1 0.102(4) 0.193(5) 0.67(2) -0.137(7) 0.131(6) -0.013(3) I2 0.0659(13) 0.1052(15) 0.1045(19) 0.0171(10) 0.0450(10) -0.0120(9) Zn1 0.0325(6) 0.0233(5) 0.0251(6) -0.0003(4) 0.0184(5) 0.0008(4) Zn2 0.0366(5) 0.0273(4) 0.0288(4) 0.0027(3) 0.0213(4) 0.0049(3) O1 0.054(3) 0.051(3) 0.034(3) -0.010(2) 0.028(3) -0.003(3) O2 0.054(4) 0.055(4) 0.042(3) 0.007(3) 0.016(3) 0.005(3) O3 0.038(3) 0.043(3) 0.027(3) -0.007(2) 0.018(2) -0.016(2) O4 0.050(3) 0.039(3) 0.038(3) 0.006(2) 0.023(3) -0.007(2) O5 0.131(8) 0.159(9) 0.053(5) -0.044(5) 0.051(5) -0.079(7) O6 0.100(6) 0.096(6) 0.072(5) -0.038(4) 0.032(5) -0.058(5) O7 0.034(3) 0.036(3) 0.031(3) 0.007(2) 0.021(2) 0.001(2) O8 0.077(7) 0.040(5) 0.077(7) 0.000 0.025(6) 0.000 N1 0.061(5) 0.067(5) 0.043(4) -0.024(4) 0.031(4) -0.026(4) N2 0.045(4) 0.028(3) 0.035(3) -0.001(2) 0.029(3) 0.005(3) N3 0.043(4) 0.034(3) 0.036(3) 0.001(3) 0.026(3) 0.008(3) C1 0.036(4) 0.028(3) 0.037(4) -0.007(3) 0.026(3) -0.003(3) C2 0.035(4) 0.029(3) 0.028(3) -0.002(3) 0.022(3) -0.003(3) C3 0.038(4) 0.043(4) 0.029(4) -0.005(3) 0.020(3) -0.004(3) C4 0.042(4) 0.040(4) 0.040(4) -0.021(3) 0.027(4) -0.012(3) C5 0.052(5) 0.036(4) 0.053(5) -0.013(4) 0.033(4) -0.014(4) C6 0.052(5) 0.037(4) 0.046(4) -0.003(3) 0.032(4) -0.011(4) C7 0.045(4) 0.038(4) 0.027(4) 0.000(3) 0.022(4) -0.013(3) C8 0.039(4) 0.026(3) 0.037(4) -0.005(3) 0.028(4) 0.000(3) C9 0.051(4) 0.032(4) 0.036(4) -0.004(3) 0.033(4) -0.003(3) C10 0.051(5) 0.027(4) 0.041(4) -0.004(3) 0.029(4) -0.002(3) C11 0.047(5) 0.035(4) 0.035(4) 0.001(3) 0.026(4) 0.010(3) C12 0.048(4) 0.038(4) 0.047(4) 0.003(3) 0.035(4) 0.004(3) C13 0.053(5) 0.029(4) 0.046(4) 0.000(3) 0.037(4) 0.001(3) C14 0.049(5) 0.039(4) 0.054(5) -0.001(4) 0.036(4) 0.006(4) C15 0.051(5) 0.036(4) 0.053(5) 0.001(3) 0.036(4) 0.008(3) C16 0.057(5) 0.034(4) 0.058(5) -0.002(4) 0.040(5) 0.004(4) C17 0.058(5) 0.037(4) 0.073(6) -0.006(4) 0.052(5) 0.000(4) C18 0.038(4) 0.039(4) 0.037(4) -0.004(3) 0.024(3) 0.010(3) C19 0.072(6) 0.027(4) 0.068(6) 0.001(4) 0.050(5) 0.004(4) C20 0.061(5) 0.043(4) 0.060(5) 0.006(4) 0.047(5) 0.009(4) _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 I1 I1 2.56(2) 2_655 ? I2 I2 2.625(5) 2_655 ? Zn1 O7 2.033(4) 5_565 ? Zn1 O7 2.033(4) . ? Zn1 N2 2.172(5) . ? Zn1 N2 2.172(5) 5_565 ? Zn1 O3 2.180(5) . ? Zn1 O3 2.180(5) 5_565 ? Zn2 O7 1.878(5) . ? Zn2 O1 1.964(5) 2_554 ? Zn2 O4 1.992(5) 5_565 ? Zn2 N3 2.058(6) 7_465 ? O1 C7 1.275(9) . ? O1 Zn2 1.964(5) 2_554 ? O2 C7 1.232(9) . ? O3 C8 1.224(8) . ? O4 C8 1.277(8) . ? O4 Zn2 1.992(5) 5_565 ? O5 N1 1.199(10) . ? O6 N1 1.194(10) . ? O7 H7D 0.8500 . ? O8 H1W 0.8471 . ? N1 C4 1.455(10) . ? N2 C9 1.326(9) . ? N2 C13 1.354(9) . ? N3 C16 1.328(9) . ? N3 C20 1.332(9) . ? N3 Zn2 2.058(6) 7_465 ? C1 C6 1.400(10) . ? C1 C2 1.403(9) . ? C1 C7 1.496(10) . ? C2 C3 1.384(9) . ? C2 C8 1.506(9) . ? C3 C4 1.373(10) . ? C3 H3 0.9300 . ? C4 C5 1.377(11) . ? C5 C6 1.387(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C9 C10 1.371(10) . ? C9 H9A 0.9300 . ? C10 C11 1.412(10) . ? C10 H10 0.9300 . ? C11 C12 1.392(10) . ? C11 C14 1.463(10) . ? C12 C13 1.363(10) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.309(11) . ? C14 H14 0.9300 . ? C15 C18 1.474(9) . ? C15 H15 0.9300 . ? C16 C17 1.372(10) . ? C16 H16 0.9300 . ? C17 C18 1.371(10) . ? C17 H17 0.9300 . ? C18 C19 1.395(11) . ? C19 C20 1.378(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Zn1 O7 180.0(2) 5_565 . ? O7 Zn1 N2 89.91(19) 5_565 . ? O7 Zn1 N2 90.09(19) . . ? O7 Zn1 N2 90.09(19) 5_565 5_565 ? O7 Zn1 N2 89.91(19) . 5_565 ? N2 Zn1 N2 180.000(1) . 5_565 ? O7 Zn1 O3 90.55(18) 5_565 . ? O7 Zn1 O3 89.45(18) . . ? N2 Zn1 O3 91.4(2) . . ? N2 Zn1 O3 88.6(2) 5_565 . ? O7 Zn1 O3 89.45(18) 5_565 5_565 ? O7 Zn1 O3 90.55(18) . 5_565 ? N2 Zn1 O3 88.6(2) . 5_565 ? N2 Zn1 O3 91.4(2) 5_565 5_565 ? O3 Zn1 O3 180.0 . 5_565 ? O7 Zn2 O1 126.3(2) . 2_554 ? O7 Zn2 O4 107.7(2) . 5_565 ? O1 Zn2 O4 98.7(2) 2_554 5_565 ? O7 Zn2 N3 116.0(2) . 7_465 ? O1 Zn2 N3 100.3(2) 2_554 7_465 ? O4 Zn2 N3 105.0(2) 5_565 7_465 ? C7 O1 Zn2 118.6(5) . 2_554 ? C8 O3 Zn1 136.8(4) . . ? C8 O4 Zn2 119.7(5) . 5_565 ? Zn2 O7 Zn1 119.4(2) . . ? Zn2 O7 H7D 113.7 . . ? Zn1 O7 H7D 120.4 . . ? O6 N1 O5 122.0(8) . . ? O6 N1 C4 119.8(8) . . ? O5 N1 C4 118.1(7) . . ? C9 N2 C13 117.3(6) . . ? C9 N2 Zn1 124.4(4) . . ? C13 N2 Zn1 118.0(4) . . ? C16 N3 C20 116.4(6) . . ? C16 N3 Zn2 121.4(5) . 7_465 ? C20 N3 Zn2 122.1(5) . 7_465 ? C6 C1 C2 118.7(6) . . ? C6 C1 C7 117.0(6) . . ? C2 C1 C7 124.3(6) . . ? C3 C2 C1 119.6(6) . . ? C3 C2 C8 120.0(6) . . ? C1 C2 C8 120.4(6) . . ? C4 C3 C2 119.9(7) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 122.3(7) . . ? C3 C4 N1 119.6(7) . . ? C5 C4 N1 118.1(7) . . ? C4 C5 C6 117.9(7) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 121.5(7) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O2 C7 O1 125.2(7) . . ? O2 C7 C1 119.6(7) . . ? O1 C7 C1 115.0(7) . . ? O3 C8 O4 126.5(6) . . ? O3 C8 C2 118.2(6) . . ? O4 C8 C2 115.3(6) . . ? N2 C9 C10 124.1(6) . . ? N2 C9 H9A 117.9 . . ? C10 C9 H9A 117.9 . . ? C9 C10 C11 118.9(7) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 116.4(6) . . ? C12 C11 C14 119.3(7) . . ? C10 C11 C14 124.2(7) . . ? C13 C12 C11 120.7(7) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N2 C13 C12 122.5(6) . . ? N2 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C15 C14 C11 127.1(7) . . ? C15 C14 H14 116.4 . . ? C11 C14 H14 116.4 . . ? C14 C15 C18 126.0(7) . . ? C14 C15 H15 117.0 . . ? C18 C15 H15 117.0 . . ? N3 C16 C17 123.8(7) . . ? N3 C16 H16 118.1 . . ? C17 C16 H16 118.1 . . ? C18 C17 C16 120.2(7) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 116.6(6) . . ? C17 C18 C15 120.5(7) . . ? C19 C18 C15 122.9(7) . . ? C20 C19 C18 119.3(7) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? N3 C20 C19 123.6(7) . . ? N3 C20 H20 118.2 . . ? C19 C20 H20 118.2 . . ? 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 O7 Zn1 O3 C8 -26.9(7) 5_565 . . . ? O7 Zn1 O3 C8 153.1(7) . . . . ? N2 Zn1 O3 C8 63.0(7) . . . . ? N2 Zn1 O3 C8 -117.0(7) 5_565 . . . ? O3 Zn1 O3 C8 -146(49) 5_565 . . . ? O1 Zn2 O7 Zn1 -155.6(2) 2_554 . . . ? O4 Zn2 O7 Zn1 -40.1(3) 5_565 . . . ? N3 Zn2 O7 Zn1 77.2(3) 7_465 . . . ? O7 Zn1 O7 Zn2 84(26) 5_565 . . . ? N2 Zn1 O7 Zn2 -70.6(3) . . . . ? N2 Zn1 O7 Zn2 109.4(3) 5_565 . . . ? O3 Zn1 O7 Zn2 -162.0(3) . . . . ? O3 Zn1 O7 Zn2 18.0(3) 5_565 . . . ? O7 Zn1 N2 C9 138.8(6) 5_565 . . . ? O7 Zn1 N2 C9 -41.2(6) . . . . ? N2 Zn1 N2 C9 -117(22) 5_565 . . . ? O3 Zn1 N2 C9 48.2(6) . . . . ? O3 Zn1 N2 C9 -131.8(6) 5_565 . . . ? O7 Zn1 N2 C13 -47.5(5) 5_565 . . . ? O7 Zn1 N2 C13 132.5(5) . . . . ? N2 Zn1 N2 C13 56(23) 5_565 . . . ? O3 Zn1 N2 C13 -138.0(5) . . . . ? O3 Zn1 N2 C13 42.0(5) 5_565 . . . ? C6 C1 C2 C3 -2.6(10) . . . . ? C7 C1 C2 C3 177.5(7) . . . . ? C6 C1 C2 C8 176.5(6) . . . . ? C7 C1 C2 C8 -3.5(10) . . . . ? C1 C2 C3 C4 2.3(10) . . . . ? C8 C2 C3 C4 -176.8(6) . . . . ? C2 C3 C4 C5 -1.6(11) . . . . ? C2 C3 C4 N1 177.7(7) . . . . ? O6 N1 C4 C3 174.6(9) . . . . ? O5 N1 C4 C3 -8.6(13) . . . . ? O6 N1 C4 C5 -6.1(13) . . . . ? O5 N1 C4 C5 170.7(9) . . . . ? C3 C4 C5 C6 1.1(12) . . . . ? N1 C4 C5 C6 -178.2(7) . . . . ? C4 C5 C6 C1 -1.5(12) . . . . ? C2 C1 C6 C5 2.2(11) . . . . ? C7 C1 C6 C5 -177.9(7) . . . . ? Zn2 O1 C7 O2 13.9(10) 2_554 . . . ? Zn2 O1 C7 C1 -161.0(4) 2_554 . . . ? C6 C1 C7 O2 -76.9(9) . . . . ? C2 C1 C7 O2 103.0(8) . . . . ? C6 C1 C7 O1 98.4(8) . . . . ? C2 C1 C7 O1 -81.7(8) . . . . ? Zn1 O3 C8 O4 40.8(11) . . . . ? Zn1 O3 C8 C2 -139.4(5) . . . . ? Zn2 O4 C8 O3 -2.9(9) 5_565 . . . ? Zn2 O4 C8 C2 177.3(4) 5_565 . . . ? C3 C2 C8 O3 167.3(6) . . . . ? C1 C2 C8 O3 -11.7(9) . . . . ? C3 C2 C8 O4 -12.8(9) . . . . ? C1 C2 C8 O4 168.1(6) . . . . ? C13 N2 C9 C10 0.1(11) . . . . ? Zn1 N2 C9 C10 173.9(6) . . . . ? N2 C9 C10 C11 0.4(12) . . . . ? C9 C10 C11 C12 -0.5(11) . . . . ? C9 C10 C11 C14 179.0(7) . . . . ? C10 C11 C12 C13 0.1(11) . . . . ? C14 C11 C12 C13 -179.4(7) . . . . ? C9 N2 C13 C12 -0.5(11) . . . . ? Zn1 N2 C13 C12 -174.7(6) . . . . ? C11 C12 C13 N2 0.4(12) . . . . ? C12 C11 C14 C15 177.1(8) . . . . ? C10 C11 C14 C15 -2.4(13) . . . . ? C11 C14 C15 C18 177.8(7) . . . . ? C20 N3 C16 C17 1.0(12) . . . . ? Zn2 N3 C16 C17 -178.8(7) 7_465 . . . ? N3 C16 C17 C18 -0.8(13) . . . . ? C16 C17 C18 C19 -0.5(12) . . . . ? C16 C17 C18 C15 178.4(8) . . . . ? C14 C15 C18 C17 -174.9(9) . . . . ? C14 C15 C18 C19 4.0(13) . . . . ? C17 C18 C19 C20 1.5(12) . . . . ? C15 C18 C19 C20 -177.4(8) . . . . ? C16 N3 C20 C19 0.1(12) . . . . ? Zn2 N3 C20 C19 179.9(7) 7_465 . . . ? C18 C19 C20 N3 -1.4(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H1W O2 0.85 1.96 2.779(9) 161.3 4_545 O7 H7D O2 0.85 2.23 3.041(8) 160.5 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.903 _refine_diff_density_min -1.928 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 972458' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H30 N6 O15.50 Zn3' _chemical_formula_weight 1038.81 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.838(19) _cell_length_b 13.844(19) _cell_length_c 14.42(3) _cell_angle_alpha 108.31(2) _cell_angle_beta 110.43(2) _cell_angle_gamma 107.046(16) _cell_volume 2191(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1196 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 1.705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7160 _exptl_absorpt_correction_T_max 0.7840 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16335 _diffrn_reflns_av_R_equivalents 0.3079 _diffrn_reflns_av_sigmaI/netI 0.7204 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8063 _reflns_number_gt 1790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8422P] 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 8063 _refine_ls_number_parameters 589 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3720 _refine_ls_R_factor_gt 0.1092 _refine_ls_wR_factor_ref 0.3804 _refine_ls_wR_factor_gt 0.2503 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.000 _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 0.8441(2) 0.6307(3) 0.3998(2) 0.0660(10) Uani 1 1 d . . . Zn2 Zn 1.0000 0.5000 0.5000 0.0540(12) Uani 1 2 d S . . Zn3 Zn 0.5000 0.5000 0.5000 0.0651(13) Uani 1 2 d S . . Zn4 Zn 0.5530(2) 0.2740(3) 0.4002(2) 0.0728(11) Uani 1 1 d . . . N1 N 0.8742(18) 0.6442(19) 0.2710(16) 0.070(6) Uani 1 1 d . . . N2 N 1.0254(16) 0.4615(17) 0.3510(15) 0.064(6) Uani 1 1 d . . . N3 N 0.3964(18) 0.142(2) 0.276(2) 0.108(9) Uani 1 1 d . . . N4 N 0.3275(19) 0.398(2) 0.3501(17) 0.083(7) Uani 1 1 d . . . N5 N 0.326(2) 0.791(2) 0.123(2) 0.101(9) Uani 1 1 d . . . N6 N 0.798(3) -0.153(3) 0.134(2) 0.099(9) Uani 1 1 d . . . O1 O 0.7283(14) 0.6849(17) 0.3863(14) 0.086(6) Uani 1 1 d . . . O2 O 0.5952(18) 0.508(2) 0.2569(16) 0.103(7) Uani 1 1 d . . . O3 O 0.5323(12) 0.6171(15) 0.4382(12) 0.078(6) Uani 1 1 d . . . O4 O 0.4450(13) 0.7281(14) 0.4626(12) 0.085(5) Uani 1 1 d . . . O5 O 0.2639(19) 0.810(2) 0.1620(19) 0.137(9) Uani 1 1 d . . . O6 O 0.337(2) 0.814(2) 0.0501(19) 0.154(10) Uani 1 1 d . . . O7 O 0.5692(11) 0.4204(14) 0.4207(10) 0.072(5) Uani 1 1 d . . . H7D H 0.5768 0.4443 0.3750 0.109 Uiso 1 1 d R . . O8 O 0.9060(11) 0.3248(14) 0.4440(11) 0.060(5) Uani 1 1 d . . . O9 O 1.0221(13) 0.2377(15) 0.4630(11) 0.077(5) Uani 1 1 d . . . O10 O 0.6647(16) 0.2573(18) 0.2583(17) 0.104(7) Uani 1 1 d . . . O11 O 0.6537(15) 0.2021(17) 0.3870(15) 0.105(8) Uani 1 1 d . . . O12 O 0.899(2) -0.130(2) 0.169(2) 0.158(11) Uani 1 1 d . . . O13 O 0.714(2) -0.244(2) 0.057(2) 0.156(11) Uani 1 1 d . . . O14 O 0.8501(11) 0.5038(13) 0.4172(10) 0.066(5) Uani 1 1 d . . . H14D H 0.7982 0.4353 0.3732 0.099 Uiso 1 1 d R . . O15 O 0.462(2) 0.6957(19) 0.8937(18) 0.201(12) Uani 1 1 d . . . H1W H 0.3926 0.6837 0.8574 0.302 Uiso 1 1 d R . . H2W H 0.4655 0.6360 0.8583 0.302 Uiso 1 1 d R . . O16 O 0.756(5) 0.010(6) 0.512(3) 0.46(8) Uani 0.50 1 d P . . H4W H 0.7957 -0.0268 0.5103 0.687 Uiso 1 1 d R . . H3W H 0.7438 0.0492 0.4781 0.687 Uiso 1 1 d R . . C1 C 0.799(2) 0.568(2) 0.1615(19) 0.069(8) Uani 1 1 d . . . H17 H 0.7227 0.5246 0.1401 0.082 Uiso 1 1 calc R . . C2 C 0.832(2) 0.555(2) 0.084(2) 0.079(9) Uani 1 1 d . . . H18 H 0.7775 0.5067 0.0091 0.094 Uiso 1 1 calc R . . C3 C 0.948(2) 0.613(2) 0.1134(18) 0.057(7) Uani 1 1 d . . . C4 C 1.021(2) 0.698(2) 0.217(2) 0.078(8) Uani 1 1 d . . . H14 H 1.0954 0.7450 0.2356 0.093 Uiso 1 1 calc R . . C5 C 0.986(2) 0.715(2) 0.297(2) 0.087(9) Uani 1 1 d . . . H15 H 1.0371 0.7749 0.3687 0.104 Uiso 1 1 calc R . . C6 C 1.0058(19) 0.585(2) 0.0475(17) 0.061(7) Uani 1 1 d . . . H33 H 1.0625 0.6543 0.0569 0.073 Uiso 1 1 calc R . . C7 C 1.0644(19) 0.507(2) 0.0759(17) 0.066(7) Uani 1 1 d . . . H34 H 1.1462 0.5436 0.0965 0.079 Uiso 1 1 calc R . . C8 C 1.0545(16) 0.480(2) 0.1631(18) 0.052(6) Uani 1 1 d . . . C9 C 1.1459(19) 0.544(2) 0.278(2) 0.076(8) Uani 1 1 d . . . H11 H 1.2194 0.5923 0.2956 0.091 Uiso 1 1 calc R . . C10 C 1.125(2) 0.533(2) 0.3651(18) 0.067(8) Uani 1 1 d . . . H13 H 1.1857 0.5786 0.4380 0.080 Uiso 1 1 calc R . . C11 C 0.9448(18) 0.397(2) 0.2479(18) 0.063(7) Uani 1 1 d . . . H10 H 0.8746 0.3437 0.2332 0.076 Uiso 1 1 calc R . . C12 C 0.9586(18) 0.403(2) 0.1545(18) 0.075(8) Uani 1 1 d . . . H12 H 0.8978 0.3500 0.0830 0.090 Uiso 1 1 calc R . . C13 C 0.3018(18) 0.358(2) 0.246(2) 0.075(8) Uani 1 1 d . . . H27 H 0.3574 0.3930 0.2297 0.090 Uiso 1 1 calc R . . C14 C 0.195(3) 0.265(3) 0.155(2) 0.107(11) Uani 1 1 d . . . H31 H 0.1854 0.2453 0.0829 0.129 Uiso 1 1 calc R . . C15 C 0.106(3) 0.202(4) 0.166(3) 0.155(18) Uani 1 1 d . . . C16 C 0.132(3) 0.251(3) 0.277(3) 0.113(12) Uani 1 1 d . . . H29 H 0.0755 0.2230 0.2955 0.136 Uiso 1 1 calc R . . C17 C 0.240(3) 0.341(3) 0.363(2) 0.094(10) Uani 1 1 d . . . H30 H 0.2518 0.3639 0.4353 0.113 Uiso 1 1 calc R . . C18 C 0.006(3) 0.084(6) 0.079(3) 0.25(3) Uani 1 1 d . . . C19 C 0.364(2) 0.106(2) 0.164(2) 0.083(9) Uani 1 1 d . . . H42 H 0.4178 0.1338 0.1427 0.100 Uiso 1 1 calc R . . C20 C 0.249(2) 0.027(2) 0.084(2) 0.077(8) Uani 1 1 d . . . H40 H 0.2280 -0.0034 0.0087 0.093 Uiso 1 1 calc R . . C21 C 0.167(2) -0.008(2) 0.114(2) 0.069(8) Uani 1 1 d . . . C22 C 0.197(2) 0.023(3) 0.220(3) 0.100(10) Uani 1 1 d . . . H39 H 0.1417 -0.0044 0.2403 0.120 Uiso 1 1 calc R . . C23 C 0.310(3) 0.094(3) 0.302(2) 0.116(12) Uani 1 1 d . . . H44 H 0.3310 0.1115 0.3757 0.139 Uiso 1 1 calc R . . C24 C 0.039(2) -0.068(5) 0.039(3) 0.19(2) Uani 1 1 d . . . C25 C 0.673(2) 0.197(3) 0.308(3) 0.082(10) Uani 1 1 d . . . C26 C 0.715(2) 0.114(2) 0.262(2) 0.075(8) Uani 1 1 d . . . C27 C 0.629(2) 0.015(3) 0.164(2) 0.085(9) Uani 1 1 d . . . H5 H 0.5548 0.0075 0.1279 0.102 Uiso 1 1 calc R . . C28 C 0.655(2) -0.075(2) 0.1213(19) 0.072(7) Uani 1 1 d . . . H4 H 0.5988 -0.1430 0.0576 0.086 Uiso 1 1 calc R . . C29 C 0.770(2) -0.058(3) 0.178(2) 0.077(9) Uani 1 1 d . . . C30 C 0.857(2) 0.038(2) 0.272(2) 0.077(8) Uani 1 1 d . . . H2 H 0.9309 0.0438 0.3054 0.093 Uiso 1 1 calc R . . C31 C 0.8307(19) 0.132(2) 0.3178(18) 0.055(7) Uani 1 1 d . . . C32 C 0.9240(18) 0.241(2) 0.4166(18) 0.059(7) Uani 1 1 d . . . C33 C 0.629(3) 0.611(3) 0.307(2) 0.073(9) Uani 1 1 d . . . C34 C 0.5413(16) 0.658(2) 0.2561(18) 0.053(6) Uani 1 1 d . . . C35 C 0.4797(16) 0.691(2) 0.3089(18) 0.067(8) Uani 1 1 d . . . C36 C 0.4124(17) 0.741(2) 0.266(2) 0.075(8) Uani 1 1 d . . . H23 H 0.3763 0.7716 0.3022 0.090 Uiso 1 1 calc R . . C37 C 0.4025(19) 0.744(2) 0.171(2) 0.072(8) Uani 1 1 d . . . C38 C 0.453(2) 0.702(2) 0.1122(18) 0.081(8) Uani 1 1 d . . . H25 H 0.4424 0.7057 0.0464 0.097 Uiso 1 1 calc R . . C39 C 0.5232(18) 0.651(2) 0.1560(19) 0.071(8) Uani 1 1 d . . . H24 H 0.5546 0.6162 0.1170 0.085 Uiso 1 1 calc R . . C40 C 0.4889(17) 0.677(2) 0.4114(17) 0.054(7) 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 0.0486(17) 0.116(3) 0.0572(17) 0.0454(19) 0.0353(14) 0.0494(18) Zn2 0.038(2) 0.083(3) 0.044(2) 0.028(2) 0.0209(18) 0.030(2) Zn3 0.062(2) 0.118(4) 0.059(2) 0.052(3) 0.045(2) 0.063(3) Zn4 0.0509(18) 0.103(3) 0.0661(19) 0.0294(19) 0.0389(16) 0.0342(19) N1 0.071(14) 0.099(18) 0.070(14) 0.051(14) 0.049(13) 0.046(14) N2 0.036(11) 0.081(17) 0.050(13) 0.021(12) 0.009(11) 0.022(12) N3 0.058(15) 0.14(2) 0.13(2) 0.063(19) 0.065(16) 0.016(15) N4 0.091(17) 0.15(2) 0.067(15) 0.064(15) 0.056(14) 0.084(17) N5 0.074(17) 0.15(3) 0.11(2) 0.09(2) 0.046(16) 0.070(18) N6 0.09(2) 0.14(3) 0.075(18) 0.06(2) 0.053(18) 0.05(2) O1 0.048(10) 0.149(19) 0.079(12) 0.061(13) 0.033(9) 0.055(12) O2 0.117(17) 0.13(2) 0.085(14) 0.059(16) 0.053(13) 0.074(18) O3 0.081(11) 0.155(17) 0.083(11) 0.084(12) 0.060(9) 0.101(12) O4 0.063(11) 0.104(15) 0.070(11) 0.035(11) 0.016(9) 0.041(11) O5 0.104(17) 0.20(3) 0.149(19) 0.114(19) 0.059(15) 0.094(18) O6 0.126(19) 0.19(2) 0.123(19) 0.107(19) 0.017(16) 0.056(17) O7 0.072(10) 0.130(16) 0.058(9) 0.057(10) 0.044(8) 0.068(11) O8 0.042(9) 0.086(14) 0.052(9) 0.017(9) 0.023(7) 0.044(10) O9 0.072(11) 0.131(16) 0.057(9) 0.049(10) 0.040(9) 0.062(11) O10 0.084(14) 0.109(19) 0.128(17) 0.057(15) 0.049(13) 0.055(13) O11 0.101(14) 0.144(19) 0.102(14) 0.037(13) 0.083(13) 0.073(14) O12 0.13(2) 0.18(3) 0.14(2) 0.025(18) 0.074(18) 0.08(2) O13 0.14(2) 0.17(3) 0.111(18) 0.029(18) 0.083(17) 0.027(19) O14 0.049(9) 0.098(13) 0.058(9) 0.027(9) 0.026(8) 0.051(9) O15 0.23(3) 0.14(2) 0.126(18) 0.035(18) 0.044(19) 0.05(2) O16 0.27(7) 0.56(12) 0.06(3) 0.09(5) 0.01(4) -0.26(7) C1 0.062(16) 0.08(2) 0.052(15) 0.027(16) 0.015(14) 0.044(16) C2 0.058(17) 0.13(3) 0.070(17) 0.044(17) 0.050(15) 0.042(18) C3 0.079(18) 0.08(2) 0.037(13) 0.032(14) 0.036(14) 0.047(17) C4 0.061(17) 0.11(3) 0.09(2) 0.06(2) 0.056(16) 0.035(18) C5 0.069(19) 0.12(3) 0.064(17) 0.044(18) 0.047(16) 0.024(19) C6 0.064(15) 0.08(2) 0.064(16) 0.038(16) 0.044(14) 0.037(15) C7 0.062(15) 0.10(2) 0.056(15) 0.039(16) 0.048(13) 0.030(16) C8 0.026(12) 0.079(19) 0.061(15) 0.035(14) 0.033(12) 0.020(13) C9 0.039(15) 0.09(2) 0.067(17) 0.021(17) 0.017(14) 0.016(15) C10 0.044(15) 0.10(2) 0.040(14) 0.025(15) 0.009(13) 0.039(16) C11 0.041(14) 0.13(2) 0.054(14) 0.053(16) 0.044(13) 0.044(16) C12 0.032(14) 0.08(2) 0.055(15) 0.002(15) 0.012(12) -0.011(14) C13 0.029(13) 0.12(3) 0.072(17) 0.041(18) 0.019(14) 0.047(16) C14 0.11(2) 0.22(4) 0.062(18) 0.08(2) 0.067(19) 0.10(3) C15 0.06(2) 0.36(6) 0.07(2) 0.11(3) 0.049(18) 0.08(3) C16 0.10(3) 0.22(4) 0.11(2) 0.11(3) 0.09(2) 0.10(3) C17 0.07(2) 0.16(3) 0.049(16) 0.042(19) 0.033(17) 0.05(2) C18 0.04(2) 0.48(9) 0.07(2) 0.10(4) 0.010(19) -0.03(4) C19 0.08(2) 0.12(3) 0.063(17) 0.052(19) 0.039(17) 0.05(2) C20 0.067(18) 0.10(2) 0.071(18) 0.030(18) 0.033(17) 0.054(18) C21 0.050(16) 0.10(2) 0.063(17) 0.054(18) 0.018(15) 0.035(16) C22 0.06(2) 0.11(3) 0.14(3) 0.08(3) 0.04(2) 0.02(2) C23 0.09(2) 0.11(3) 0.062(18) -0.004(19) 0.026(19) 0.01(2) C24 0.041(17) 0.41(6) 0.13(3) 0.18(4) 0.035(19) 0.07(3) C25 0.037(14) 0.07(2) 0.10(2) 0.01(2) 0.013(16) 0.024(16) C26 0.068(18) 0.10(2) 0.083(18) 0.039(19) 0.053(17) 0.049(19) C27 0.060(17) 0.11(3) 0.079(19) 0.024(19) 0.044(16) 0.039(19) C28 0.065(18) 0.05(2) 0.069(17) 0.018(15) 0.030(15) 0.007(16) C29 0.08(2) 0.08(2) 0.081(19) 0.017(18) 0.065(18) 0.05(2) C30 0.076(19) 0.09(2) 0.11(2) 0.05(2) 0.072(19) 0.058(19) C31 0.057(15) 0.08(2) 0.069(16) 0.044(16) 0.049(14) 0.040(16) C32 0.025(13) 0.08(2) 0.048(15) 0.020(16) 0.018(12) 0.008(15) C33 0.10(2) 0.10(3) 0.07(2) 0.06(2) 0.06(2) 0.06(3) C34 0.036(12) 0.10(2) 0.065(15) 0.062(15) 0.032(12) 0.046(14) C35 0.026(12) 0.11(2) 0.078(17) 0.056(17) 0.039(12) 0.022(14) C36 0.037(14) 0.11(3) 0.070(17) 0.043(18) 0.027(13) 0.029(16) C37 0.058(16) 0.10(2) 0.10(2) 0.073(19) 0.037(16) 0.059(17) C38 0.084(19) 0.13(3) 0.061(16) 0.069(18) 0.035(15) 0.057(19) C39 0.065(16) 0.10(2) 0.073(17) 0.049(17) 0.040(14) 0.052(17) C40 0.043(13) 0.09(2) 0.064(15) 0.043(15) 0.044(12) 0.039(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 O14 1.873(15) . ? Zn1 O1 1.934(15) . ? Zn1 O9 1.965(16) 2_766 ? Zn1 N1 2.090(19) . ? Zn2 O14 2.026(12) . ? Zn2 O14 2.026(12) 2_766 ? Zn2 O8 2.101(17) . ? Zn2 O8 2.101(17) 2_766 ? Zn2 N2 2.223(19) 2_766 ? Zn2 N2 2.223(19) . ? Zn3 O7 2.007(13) 2_666 ? Zn3 O7 2.007(13) . ? Zn3 O3 2.094(17) . ? Zn3 O3 2.094(17) 2_666 ? Zn3 N4 2.21(2) . ? Zn3 N4 2.21(2) 2_666 ? Zn4 O7 1.885(16) . ? Zn4 O11 1.962(16) . ? Zn4 O4 1.977(17) 2_666 ? Zn4 N3 2.04(2) . ? N1 C1 1.36(2) . ? N1 C5 1.41(3) . ? N2 C11 1.29(2) . ? N2 C10 1.34(3) . ? N3 C19 1.38(3) . ? N3 C23 1.41(3) . ? N4 C13 1.29(3) . ? N4 C17 1.35(3) . ? N5 O5 1.22(3) . ? N5 O6 1.24(3) . ? N5 C37 1.49(3) . ? N6 O12 1.21(3) . ? N6 O13 1.24(3) . ? N6 C29 1.50(3) . ? O1 C33 1.26(3) . ? O2 C33 1.23(3) . ? O3 C40 1.23(2) . ? O4 C40 1.29(2) . ? O4 Zn4 1.977(17) 2_666 ? O7 H7D 0.8501 . ? O8 C32 1.23(3) . ? O9 C32 1.31(2) . ? O9 Zn1 1.965(16) 2_766 ? O10 C25 1.27(3) . ? O11 C25 1.24(3) . ? O14 H14D 0.8500 . ? O15 H1W 0.8501 . ? O15 H2W 0.8500 . ? O16 H4W 0.8498 . ? O16 H3W 0.8501 . ? C1 C2 1.33(3) . ? C1 H17 0.9300 . ? C2 C3 1.40(3) . ? C2 H18 0.9300 . ? C3 C4 1.33(3) . ? C3 C6 1.47(3) . ? C4 C5 1.38(3) . ? C4 H14 0.9300 . ? C5 H15 0.9300 . ? C6 C7 1.54(3) 2_765 ? C6 C7 1.60(3) . ? C6 H33 0.9800 . ? C7 C8 1.46(3) . ? C7 C6 1.54(3) 2_765 ? C7 H34 0.9800 . ? C8 C12 1.37(3) . ? C8 C9 1.45(3) . ? C9 C10 1.42(3) . ? C9 H11 0.9300 . ? C10 H13 0.9300 . ? C11 C12 1.45(3) . ? C11 H10 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.43(3) . ? C13 H27 0.9300 . ? C14 C15 1.38(4) . ? C14 H31 0.9300 . ? C15 C16 1.39(3) . ? C15 C18 1.52(5) . ? C16 C17 1.40(3) . ? C16 H29 0.9300 . ? C17 H30 0.9300 . ? C18 C24 1.50(4) 2 ? C19 C20 1.41(3) . ? C19 H42 0.9300 . ? C20 C21 1.36(3) . ? C20 H40 0.9300 . ? C21 C22 1.32(3) . ? C21 C24 1.50(3) . ? C22 C23 1.37(3) . ? C22 H39 0.9300 . ? C23 H44 0.9300 . ? C24 C18 1.50(4) 2 ? C25 C26 1.52(3) . ? C26 C27 1.40(3) . ? C26 C31 1.41(3) . ? C27 C28 1.41(3) . ? C27 H5 0.9300 . ? C28 C29 1.41(3) . ? C28 H4 0.9300 . ? C29 C30 1.35(3) . ? C30 C31 1.48(3) . ? C30 H2 0.9300 . ? C31 C32 1.48(3) . ? C33 C34 1.60(3) . ? C34 C39 1.35(3) . ? C34 C35 1.41(3) . ? C35 C36 1.41(3) . ? C35 C40 1.52(3) . ? C36 C37 1.34(3) . ? C36 H23 0.9300 . ? C37 C38 1.38(3) . ? C38 C39 1.44(3) . ? C38 H25 0.9300 . ? C39 H24 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O14 Zn1 O1 130.7(7) . . ? O14 Zn1 O9 104.3(6) . 2_766 ? O1 Zn1 O9 100.0(7) . 2_766 ? O14 Zn1 N1 113.6(7) . . ? O1 Zn1 N1 100.4(7) . . ? O9 Zn1 N1 104.5(8) 2_766 . ? O14 Zn2 O14 180.000(4) . 2_766 ? O14 Zn2 O8 89.2(6) . . ? O14 Zn2 O8 90.8(6) 2_766 . ? O14 Zn2 O8 90.8(6) . 2_766 ? O14 Zn2 O8 89.2(6) 2_766 2_766 ? O8 Zn2 O8 180.0(8) . 2_766 ? O14 Zn2 N2 88.8(6) . 2_766 ? O14 Zn2 N2 91.2(6) 2_766 2_766 ? O8 Zn2 N2 89.6(6) . 2_766 ? O8 Zn2 N2 90.4(6) 2_766 2_766 ? O14 Zn2 N2 91.2(6) . . ? O14 Zn2 N2 88.8(6) 2_766 . ? O8 Zn2 N2 90.4(6) . . ? O8 Zn2 N2 89.6(6) 2_766 . ? N2 Zn2 N2 180.000(3) 2_766 . ? O7 Zn3 O7 180.000(4) 2_666 . ? O7 Zn3 O3 91.3(6) 2_666 . ? O7 Zn3 O3 88.7(6) . . ? O7 Zn3 O3 88.7(6) 2_666 2_666 ? O7 Zn3 O3 91.3(6) . 2_666 ? O3 Zn3 O3 180.0(6) . 2_666 ? O7 Zn3 N4 88.4(7) 2_666 . ? O7 Zn3 N4 91.6(6) . . ? O3 Zn3 N4 87.6(8) . . ? O3 Zn3 N4 92.4(8) 2_666 . ? O7 Zn3 N4 91.6(6) 2_666 2_666 ? O7 Zn3 N4 88.4(6) . 2_666 ? O3 Zn3 N4 92.4(8) . 2_666 ? O3 Zn3 N4 87.6(8) 2_666 2_666 ? N4 Zn3 N4 180.000(4) . 2_666 ? O7 Zn4 O11 131.2(8) . . ? O7 Zn4 O4 103.9(6) . 2_666 ? O11 Zn4 O4 99.4(8) . 2_666 ? O7 Zn4 N3 115.2(9) . . ? O11 Zn4 N3 99.9(9) . . ? O4 Zn4 N3 103.3(9) 2_666 . ? C1 N1 C5 116(2) . . ? C1 N1 Zn1 122.6(18) . . ? C5 N1 Zn1 119.2(16) . . ? C11 N2 C10 115(2) . . ? C11 N2 Zn2 125.9(15) . . ? C10 N2 Zn2 116.8(15) . . ? C19 N3 C23 117(2) . . ? C19 N3 Zn4 122.3(19) . . ? C23 N3 Zn4 120(2) . . ? C13 N4 C17 111(2) . . ? C13 N4 Zn3 128.6(18) . . ? C17 N4 Zn3 117.0(17) . . ? O5 N5 O6 126(3) . . ? O5 N5 C37 119(3) . . ? O6 N5 C37 114(3) . . ? O12 N6 O13 127(3) . . ? O12 N6 C29 117(3) . . ? O13 N6 C29 116(3) . . ? C33 O1 Zn1 113.2(18) . . ? C40 O3 Zn3 137.1(14) . . ? C40 O4 Zn4 123.1(15) . 2_666 ? Zn4 O7 Zn3 122.5(8) . . ? Zn4 O7 H7D 121.9 . . ? Zn3 O7 H7D 110.0 . . ? C32 O8 Zn2 135.5(14) . . ? C32 O9 Zn1 121.3(16) . 2_766 ? C25 O11 Zn4 113.7(19) . . ? Zn1 O14 Zn2 123.3(8) . . ? Zn1 O14 H14D 124.7 . . ? Zn2 O14 H14D 107.9 . . ? H1W O15 H2W 105.9 . . ? H4W O16 H3W 129.1 . . ? C2 C1 N1 122(2) . . ? C2 C1 H17 119.0 . . ? N1 C1 H17 119.0 . . ? C1 C2 C3 121(2) . . ? C1 C2 H18 119.6 . . ? C3 C2 H18 119.6 . . ? C4 C3 C2 118(2) . . ? C4 C3 C6 114(2) . . ? C2 C3 C6 128(2) . . ? C3 C4 C5 120(2) . . ? C3 C4 H14 119.9 . . ? C5 C4 H14 119.9 . . ? C4 C5 N1 121(2) . . ? C4 C5 H15 119.5 . . ? N1 C5 H15 119.5 . . ? C3 C6 C7 121(2) . 2_765 ? C3 C6 C7 112.7(18) . . ? C7 C6 C7 88.7(18) 2_765 . ? C3 C6 H33 110.8 . . ? C7 C6 H33 110.8 2_765 . ? C7 C6 H33 110.8 . . ? C8 C7 C6 121(2) . 2_765 ? C8 C7 C6 115.2(18) . . ? C6 C7 C6 91.3(18) 2_765 . ? C8 C7 H34 109.4 . . ? C6 C7 H34 109.4 2_765 . ? C6 C7 H34 109.4 . . ? C12 C8 C9 110(2) . . ? C12 C8 C7 128(2) . . ? C9 C8 C7 122(2) . . ? C10 C9 C8 121(2) . . ? C10 C9 H11 119.5 . . ? C8 C9 H11 119.5 . . ? N2 C10 C9 126(2) . . ? N2 C10 H13 117.2 . . ? C9 C10 H13 117.2 . . ? N2 C11 C12 123(2) . . ? N2 C11 H10 118.5 . . ? C12 C11 H10 118.5 . . ? C8 C12 C11 125(2) . . ? C8 C12 H12 117.4 . . ? C11 C12 H12 117.4 . . ? N4 C13 C14 126(3) . . ? N4 C13 H27 117.2 . . ? C14 C13 H27 117.2 . . ? C15 C14 C13 124(2) . . ? C15 C14 H31 117.9 . . ? C13 C14 H31 117.9 . . ? C14 C15 C16 109(3) . . ? C14 C15 C18 127(3) . . ? C16 C15 C18 123(3) . . ? C15 C16 C17 123(3) . . ? C15 C16 H29 118.6 . . ? C17 C16 H29 118.6 . . ? N4 C17 C16 126(2) . . ? N4 C17 H30 116.8 . . ? C16 C17 H30 116.8 . . ? C24 C18 C15 114(5) 2 . ? N3 C19 C20 119(2) . . ? N3 C19 H42 120.7 . . ? C20 C19 H42 120.7 . . ? C21 C20 C19 122(2) . . ? C21 C20 H40 119.2 . . ? C19 C20 H40 119.2 . . ? C22 C21 C20 120(2) . . ? C22 C21 C24 113(3) . . ? C20 C21 C24 126(3) . . ? C21 C22 C23 120(3) . . ? C21 C22 H39 119.9 . . ? C23 C22 H39 119.9 . . ? C22 C23 N3 122(3) . . ? C22 C23 H44 119.1 . . ? N3 C23 H44 119.1 . . ? C18 C24 C21 118(3) 2 . ? O11 C25 O10 128(3) . . ? O11 C25 C26 121(3) . . ? O10 C25 C26 111(3) . . ? C27 C26 C31 123(2) . . ? C27 C26 C25 114(2) . . ? C31 C26 C25 122(2) . . ? C26 C27 C28 119(2) . . ? C26 C27 H5 120.5 . . ? C28 C27 H5 120.5 . . ? C27 C28 C29 118(2) . . ? C27 C28 H4 121.1 . . ? C29 C28 H4 121.1 . . ? C30 C29 C28 126(2) . . ? C30 C29 N6 116(2) . . ? C28 C29 N6 118(3) . . ? C29 C30 C31 117(2) . . ? C29 C30 H2 121.4 . . ? C31 C30 H2 121.3 . . ? C26 C31 C30 117(2) . . ? C26 C31 C32 123(2) . . ? C30 C31 C32 120(2) . . ? O8 C32 O9 126(2) . . ? O8 C32 C31 120(2) . . ? O9 C32 C31 114(2) . . ? O2 C33 O1 127(3) . . ? O2 C33 C34 116(3) . . ? O1 C33 C34 117(3) . . ? C39 C34 C35 123.5(19) . . ? C39 C34 C33 115.3(19) . . ? C35 C34 C33 120.8(19) . . ? C34 C35 C36 118(2) . . ? C34 C35 C40 121(2) . . ? C36 C35 C40 121(2) . . ? C37 C36 C35 117(2) . . ? C37 C36 H23 121.3 . . ? C35 C36 H23 121.3 . . ? C36 C37 C38 125(2) . . ? C36 C37 N5 117(3) . . ? C38 C37 N5 118(3) . . ? C37 C38 C39 118(2) . . ? C37 C38 H25 121.1 . . ? C39 C38 H25 121.1 . . ? C34 C39 C38 117(2) . . ? C34 C39 H24 121.6 . . ? C38 C39 H24 121.6 . . ? O3 C40 O4 125(2) . . ? O3 C40 C35 120.6(19) . . ? O4 C40 C35 115(2) . . ? 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 O14 Zn1 N1 C1 67.6(18) . . . . ? O1 Zn1 N1 C1 -76.0(18) . . . . ? O9 Zn1 N1 C1 -179.3(16) 2_766 . . . ? O14 Zn1 N1 C5 -96.4(19) . . . . ? O1 Zn1 N1 C5 120.0(19) . . . . ? O9 Zn1 N1 C5 17(2) 2_766 . . . ? O14 Zn2 N2 C11 -37(2) . . . . ? O14 Zn2 N2 C11 143(2) 2_766 . . . ? O8 Zn2 N2 C11 52(2) . . . . ? O8 Zn2 N2 C11 -128(2) 2_766 . . . ? N2 Zn2 N2 C11 105(100) 2_766 . . . ? O14 Zn2 N2 C10 124.2(16) . . . . ? O14 Zn2 N2 C10 -55.8(16) 2_766 . . . ? O8 Zn2 N2 C10 -146.5(16) . . . . ? O8 Zn2 N2 C10 33.5(16) 2_766 . . . ? N2 Zn2 N2 C10 -94(100) 2_766 . . . ? O7 Zn4 N3 C19 74(2) . . . . ? O11 Zn4 N3 C19 -71(2) . . . . ? O4 Zn4 N3 C19 -173(2) 2_666 . . . ? O7 Zn4 N3 C23 -97(2) . . . . ? O11 Zn4 N3 C23 118(2) . . . . ? O4 Zn4 N3 C23 15(3) 2_666 . . . ? O7 Zn3 N4 C13 147(2) 2_666 . . . ? O7 Zn3 N4 C13 -33(2) . . . . ? O3 Zn3 N4 C13 56(2) . . . . ? O3 Zn3 N4 C13 -124(2) 2_666 . . . ? N4 Zn3 N4 C13 18(100) 2_666 . . . ? O7 Zn3 N4 C17 -54(2) 2_666 . . . ? O7 Zn3 N4 C17 126(2) . . . . ? O3 Zn3 N4 C17 -146(2) . . . . ? O3 Zn3 N4 C17 34(2) 2_666 . . . ? N4 Zn3 N4 C17 176(100) 2_666 . . . ? O14 Zn1 O1 C33 -56.2(19) . . . . ? O9 Zn1 O1 C33 -175.1(17) 2_766 . . . ? N1 Zn1 O1 C33 78.0(18) . . . . ? O7 Zn3 O3 C40 -30(2) 2_666 . . . ? O7 Zn3 O3 C40 150(2) . . . . ? O3 Zn3 O3 C40 -177(100) 2_666 . . . ? N4 Zn3 O3 C40 59(2) . . . . ? N4 Zn3 O3 C40 -121(2) 2_666 . . . ? O11 Zn4 O7 Zn3 -150.8(8) . . . . ? O4 Zn4 O7 Zn3 -34.7(9) 2_666 . . . ? N3 Zn4 O7 Zn3 77.5(11) . . . . ? O7 Zn3 O7 Zn4 16(100) 2_666 . . . ? O3 Zn3 O7 Zn4 -166.7(8) . . . . ? O3 Zn3 O7 Zn4 13.3(8) 2_666 . . . ? N4 Zn3 O7 Zn4 -79.1(9) . . . . ? N4 Zn3 O7 Zn4 100.9(9) 2_666 . . . ? O14 Zn2 O8 C32 146(2) . . . . ? O14 Zn2 O8 C32 -34(2) 2_766 . . . ? O8 Zn2 O8 C32 157(100) 2_766 . . . ? N2 Zn2 O8 C32 -125(2) 2_766 . . . ? N2 Zn2 O8 C32 55(2) . . . . ? O7 Zn4 O11 C25 -59(2) . . . . ? O4 Zn4 O11 C25 -176(2) 2_666 . . . ? N3 Zn4 O11 C25 78(2) . . . . ? O1 Zn1 O14 Zn2 -149.8(8) . . . . ? O9 Zn1 O14 Zn2 -32.6(8) 2_766 . . . ? N1 Zn1 O14 Zn2 80.5(10) . . . . ? O14 Zn2 O14 Zn1 -118(100) 2_766 . . . ? O8 Zn2 O14 Zn1 -171.4(8) . . . . ? O8 Zn2 O14 Zn1 8.6(8) 2_766 . . . ? N2 Zn2 O14 Zn1 98.9(8) 2_766 . . . ? N2 Zn2 O14 Zn1 -81.1(8) . . . . ? C5 N1 C1 C2 6(3) . . . . ? Zn1 N1 C1 C2 -158.9(19) . . . . ? N1 C1 C2 C3 5(4) . . . . ? C1 C2 C3 C4 -13(4) . . . . ? C1 C2 C3 C6 160(2) . . . . ? C2 C3 C4 C5 10(4) . . . . ? C6 C3 C4 C5 -164(2) . . . . ? C3 C4 C5 N1 1(4) . . . . ? C1 N1 C5 C4 -8(4) . . . . ? Zn1 N1 C5 C4 157(2) . . . . ? C4 C3 C6 C7 -177(2) . . . 2_765 ? C2 C3 C6 C7 10(4) . . . 2_765 ? C4 C3 C6 C7 80(3) . . . . ? C2 C3 C6 C7 -93(3) . . . . ? C3 C6 C7 C8 -2(3) . . . . ? C7 C6 C7 C8 -125(2) 2_765 . . . ? C3 C6 C7 C6 123(2) . . . 2_765 ? C7 C6 C7 C6 0.000(3) 2_765 . . 2_765 ? C6 C7 C8 C12 -32(4) 2_765 . . . ? C6 C7 C8 C12 76(3) . . . . ? C6 C7 C8 C9 155(2) 2_765 . . . ? C6 C7 C8 C9 -97(2) . . . . ? C12 C8 C9 C10 -8(3) . . . . ? C7 C8 C9 C10 166(2) . . . . ? C11 N2 C10 C9 2(3) . . . . ? Zn2 N2 C10 C9 -161.4(19) . . . . ? C8 C9 C10 N2 4(4) . . . . ? C10 N2 C11 C12 -2(3) . . . . ? Zn2 N2 C11 C12 159.5(16) . . . . ? C9 C8 C12 C11 8(3) . . . . ? C7 C8 C12 C11 -165(2) . . . . ? N2 C11 C12 C8 -3(4) . . . . ? C17 N4 C13 C14 -1(4) . . . . ? Zn3 N4 C13 C14 158.6(19) . . . . ? N4 C13 C14 C15 -2(5) . . . . ? C13 C14 C15 C16 6(5) . . . . ? C13 C14 C15 C18 -162(4) . . . . ? C14 C15 C16 C17 -8(5) . . . . ? C18 C15 C16 C17 161(4) . . . . ? C13 N4 C17 C16 -1(4) . . . . ? Zn3 N4 C17 C16 -163(2) . . . . ? C15 C16 C17 N4 6(5) . . . . ? C14 C15 C18 C24 -38(8) . . . 2 ? C16 C15 C18 C24 155(4) . . . 2 ? C23 N3 C19 C20 1(4) . . . . ? Zn4 N3 C19 C20 -170.3(18) . . . . ? N3 C19 C20 C21 6(4) . . . . ? C19 C20 C21 C22 -8(4) . . . . ? C19 C20 C21 C24 164(4) . . . . ? C20 C21 C22 C23 4(5) . . . . ? C24 C21 C22 C23 -170(3) . . . . ? C21 C22 C23 N3 3(5) . . . . ? C19 N3 C23 C22 -6(5) . . . . ? Zn4 N3 C23 C22 166(2) . . . . ? C22 C21 C24 C18 167(6) . . . 2 ? C20 C21 C24 C18 -6(8) . . . 2 ? Zn4 O11 C25 O10 21(4) . . . . ? Zn4 O11 C25 C26 -160.3(18) . . . . ? O11 C25 C26 C27 99(3) . . . . ? O10 C25 C26 C27 -82(3) . . . . ? O11 C25 C26 C31 -76(4) . . . . ? O10 C25 C26 C31 103(3) . . . . ? C31 C26 C27 C28 3(4) . . . . ? C25 C26 C27 C28 -172(3) . . . . ? C26 C27 C28 C29 -2(4) . . . . ? C27 C28 C29 C30 0(4) . . . . ? C27 C28 C29 N6 180(2) . . . . ? O12 N6 C29 C30 -14(4) . . . . ? O13 N6 C29 C30 171(3) . . . . ? O12 N6 C29 C28 166(3) . . . . ? O13 N6 C29 C28 -8(4) . . . . ? C28 C29 C30 C31 0(4) . . . . ? N6 C29 C30 C31 -179(2) . . . . ? C27 C26 C31 C30 -3(4) . . . . ? C25 C26 C31 C30 172(3) . . . . ? C27 C26 C31 C32 176(2) . . . . ? C25 C26 C31 C32 -10(4) . . . . ? C29 C30 C31 C26 1(3) . . . . ? C29 C30 C31 C32 -177(2) . . . . ? Zn2 O8 C32 O9 37(3) . . . . ? Zn2 O8 C32 C31 -138.3(16) . . . . ? Zn1 O9 C32 O8 8(3) 2_766 . . . ? Zn1 O9 C32 C31 -176.6(13) 2_766 . . . ? C26 C31 C32 O8 -10(3) . . . . ? C30 C31 C32 O8 168(2) . . . . ? C26 C31 C32 O9 174(2) . . . . ? C30 C31 C32 O9 -8(3) . . . . ? Zn1 O1 C33 O2 17(3) . . . . ? Zn1 O1 C33 C34 -155.4(15) . . . . ? O2 C33 C34 C39 -68(3) . . . . ? O1 C33 C34 C39 105(3) . . . . ? O2 C33 C34 C35 106(3) . . . . ? O1 C33 C34 C35 -81(3) . . . . ? C39 C34 C35 C36 -13(4) . . . . ? C33 C34 C35 C36 174(2) . . . . ? C39 C34 C35 C40 169(2) . . . . ? C33 C34 C35 C40 -4(4) . . . . ? C34 C35 C36 C37 6(3) . . . . ? C40 C35 C36 C37 -176(2) . . . . ? C35 C36 C37 C38 0(4) . . . . ? C35 C36 C37 N5 177(2) . . . . ? O5 N5 C37 C36 -10(4) . . . . ? O6 N5 C37 C36 166(3) . . . . ? O5 N5 C37 C38 167(3) . . . . ? O6 N5 C37 C38 -17(4) . . . . ? C36 C37 C38 C39 0(4) . . . . ? N5 C37 C38 C39 -177(2) . . . . ? C35 C34 C39 C38 12(4) . . . . ? C33 C34 C39 C38 -175(2) . . . . ? C37 C38 C39 C34 -5(4) . . . . ? Zn3 O3 C40 O4 38(4) . . . . ? Zn3 O3 C40 C35 -140.0(17) . . . . ? Zn4 O4 C40 O3 3(3) 2_666 . . . ? Zn4 O4 C40 C35 -179.0(13) 2_666 . . . ? C34 C35 C40 O3 -14(3) . . . . ? C36 C35 C40 O3 169(2) . . . . ? C34 C35 C40 O4 168(2) . . . . ? C36 C35 C40 O4 -9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.799 _refine_diff_density_min -0.809 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 972459'