# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_lb _database_code_depnum_ccdc_archive 'CCDC 831974' #TrackingRef '3-L.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 N3 O4 Zn' _chemical_formula_sum 'C35 H25 N3 O4 Zn' _chemical_formula_weight 616.97 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 _symmetry_space_group_name_Hall '-C 2yc' 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 19.352(4) _cell_length_b 13.626(3) _cell_length_c 11.721(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.01(3) _cell_angle_gamma 90.00 _cell_volume 2955.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 16227 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 28.37 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.875 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.675 _exptl_absorpt_correction_T_max 0.769 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16227 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3646 _reflns_number_gt 2949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0526P)^2^+1.6646P] 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 3646 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.0000 0.20798(2) 0.7500 0.04564(12) Uani 1 2 d S . . O1 O 0.06639(8) 0.30289(10) 0.71341(15) 0.0601(4) Uani 1 1 d . . . O2 O 0.12126(11) 0.19378(12) 0.6320(2) 0.0857(6) Uani 1 1 d . . . N1 N 0.07152(9) 0.16685(12) 0.92416(16) 0.0541(4) Uani 1 1 d . . . N2 N 0.0000 0.05551(14) 0.7500 0.0388(4) Uani 1 2 d S . . C1 C 0.10755(15) 0.22921(17) 1.0091(2) 0.0738(7) Uani 1 1 d . . . H1 H 0.1049 0.2960 0.9923 0.089 Uiso 1 1 calc R . . C2 C 0.14793(16) 0.19873(18) 1.1193(2) 0.0784(8) Uani 1 1 d . . . H2 H 0.1730 0.2440 1.1756 0.094 Uiso 1 1 calc R . . C3 C 0.15108(12) 0.10029(18) 1.1460(2) 0.0626(5) Uani 1 1 d . . . H3 H 0.1772 0.0782 1.2214 0.075 Uiso 1 1 calc R . . C4 C 0.11499(10) 0.03478(14) 1.05946(18) 0.0491(4) Uani 1 1 d . . . H4 H 0.1167 -0.0322 1.0752 0.059 Uiso 1 1 calc R . . C5 C 0.07637(9) 0.07032(13) 0.94905(16) 0.0420(4) Uani 1 1 d . . . C6 C -0.03736(9) 0.00648(12) 0.65251(16) 0.0401(4) Uani 1 1 d . . . C7 C -0.03886(9) -0.09536(13) 0.65010(16) 0.0433(4) Uani 1 1 d . . . H7 H -0.0657 -0.1282 0.5820 0.052 Uiso 1 1 calc R . . C8 C 0.0000 -0.14838(17) 0.7500 0.0424(5) Uani 1 2 d S . . C9 C 0.0000 -0.25764(18) 0.7500 0.0467(6) Uani 1 2 d S . . C10 C 0.01937(16) -0.31016(16) 0.8548(2) 0.0760(7) Uani 1 1 d . . . H10 H 0.0326 -0.2770 0.9273 0.091 Uiso 1 1 calc R . . C11 C 0.01942(16) -0.41215(18) 0.8537(3) 0.0868(8) Uani 1 1 d . . . H11 H 0.0331 -0.4462 0.9256 0.104 Uiso 1 1 calc R . . C12 C 0.0000 -0.4627(2) 0.7500 0.0716(10) Uani 1 2 d S . . H12 H 0.0000 -0.5310 0.7500 0.086 Uiso 1 2 calc SR . . C31 C 0.11333(11) 0.27738(14) 0.66327(18) 0.0503(4) Uani 1 1 d . . . C32 C 0.15867(10) 0.35971(15) 0.63779(18) 0.0519(5) Uani 1 1 d . . . C33 C 0.16019(12) 0.45050(16) 0.6892(3) 0.0701(6) Uani 1 1 d . . . H33 H 0.1351 0.4611 0.7447 0.084 Uiso 1 1 calc R . . C34 C 0.19906(16) 0.52647(19) 0.6586(4) 0.1020(11) Uani 1 1 d . . . H34 H 0.2000 0.5876 0.6942 0.122 Uiso 1 1 calc R . . C35 C 0.23581(17) 0.5127(3) 0.5774(4) 0.1100(13) Uani 1 1 d . . . H35 H 0.2612 0.5644 0.5568 0.132 Uiso 1 1 calc R . . C36 C 0.23524(17) 0.4236(4) 0.5267(3) 0.1100(12) Uani 1 1 d . . . H36 H 0.2604 0.4142 0.4710 0.132 Uiso 1 1 calc R . . C37 C 0.19761(14) 0.3460(3) 0.5566(2) 0.0817(8) Uani 1 1 d . . . H37 H 0.1984 0.2847 0.5222 0.098 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 0.0564(2) 0.02613(16) 0.0613(2) 0.000 0.02802(15) 0.000 O1 0.0683(9) 0.0413(8) 0.0867(11) -0.0007(7) 0.0476(8) -0.0047(6) O2 0.1080(15) 0.0497(10) 0.1181(16) -0.0269(10) 0.0625(13) -0.0097(9) N1 0.0677(11) 0.0327(8) 0.0626(10) -0.0052(7) 0.0200(8) -0.0044(7) N2 0.0418(10) 0.0298(10) 0.0492(11) 0.000 0.0202(9) 0.000 C1 0.0995(19) 0.0389(11) 0.0758(16) -0.0104(11) 0.0145(14) -0.0109(11) C2 0.0973(19) 0.0551(15) 0.0705(16) -0.0179(12) 0.0053(14) -0.0143(12) C3 0.0647(13) 0.0604(14) 0.0593(13) -0.0079(11) 0.0128(10) -0.0005(10) C4 0.0497(10) 0.0423(10) 0.0578(11) -0.0022(8) 0.0195(8) 0.0031(8) C5 0.0430(9) 0.0350(9) 0.0530(10) -0.0043(7) 0.0218(8) -0.0006(7) C6 0.0410(8) 0.0322(8) 0.0526(10) 0.0008(7) 0.0222(7) 0.0006(6) C7 0.0470(9) 0.0322(9) 0.0518(10) -0.0019(7) 0.0163(8) -0.0026(7) C8 0.0461(13) 0.0279(12) 0.0576(15) 0.000 0.0221(11) 0.000 C9 0.0466(14) 0.0290(12) 0.0641(17) 0.000 0.0156(12) 0.000 C10 0.106(2) 0.0376(11) 0.0741(16) 0.0050(10) 0.0096(14) -0.0079(11) C11 0.109(2) 0.0382(12) 0.102(2) 0.0189(13) 0.0122(16) -0.0018(13) C12 0.0598(18) 0.0289(14) 0.123(3) 0.000 0.0220(19) 0.000 C31 0.0563(11) 0.0450(11) 0.0533(11) -0.0030(8) 0.0218(9) -0.0018(8) C32 0.0477(10) 0.0548(12) 0.0578(11) 0.0082(9) 0.0223(9) 0.0011(8) C33 0.0627(13) 0.0443(12) 0.115(2) 0.0091(13) 0.0443(13) 0.0040(10) C34 0.0782(18) 0.0483(14) 0.190(4) 0.0303(18) 0.055(2) 0.0050(12) C35 0.0765(19) 0.106(3) 0.154(3) 0.067(3) 0.045(2) -0.0072(18) C36 0.084(2) 0.167(4) 0.094(2) 0.026(2) 0.0479(17) -0.026(2) C37 0.0725(16) 0.110(2) 0.0749(16) -0.0080(15) 0.0408(13) -0.0159(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9569(14) 2_556 ? Zn1 O1 1.9569(14) . ? Zn1 N2 2.078(2) . ? Zn1 N1 2.1780(19) 2_556 ? Zn1 N1 2.1780(19) . ? O1 C31 1.266(2) . ? O2 C31 1.220(2) . ? N1 C5 1.345(2) . ? N1 C1 1.339(3) . ? N2 C6 1.338(2) . ? N2 C6 1.338(2) 2_556 ? C1 C2 1.364(4) . ? C1 H1 0.9300 . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.489(2) 2_556 ? C6 C7 1.388(2) . ? C6 C5 1.489(2) 2_556 ? C7 C8 1.394(2) . ? C7 H7 0.9300 . ? C8 C7 1.394(2) 2_556 ? C8 C9 1.489(3) . ? C9 C10 1.375(3) 2_556 ? C9 C10 1.375(3) . ? C10 C11 1.390(3) . ? C10 H10 0.9300 . ? C11 C12 1.352(3) . ? C11 H11 0.9300 . ? C12 C11 1.352(3) 2_556 ? C12 H12 0.9300 . ? C31 C32 1.507(3) . ? C32 C33 1.372(3) . ? C32 C37 1.388(3) . ? C33 C34 1.387(3) . ? C33 H33 0.9300 . ? C34 C35 1.357(5) . ? C34 H34 0.9300 . ? C35 C36 1.351(5) . ? C35 H35 0.9300 . ? C36 C37 1.385(4) . ? C36 H36 0.9300 . ? C37 H37 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 O1 Zn1 O1 97.27(8) 2_556 . ? O1 Zn1 N2 131.36(4) 2_556 . ? O1 Zn1 N2 131.36(4) . . ? O1 Zn1 N1 95.60(7) 2_556 2_556 ? O1 Zn1 N1 104.04(7) . 2_556 ? N2 Zn1 N1 75.09(4) . 2_556 ? O1 Zn1 N1 104.04(7) 2_556 . ? O1 Zn1 N1 95.60(7) . . ? N2 Zn1 N1 75.09(4) . . ? N1 Zn1 N1 150.17(9) 2_556 . ? C31 O1 Zn1 121.76(13) . . ? C5 N1 C1 118.11(19) . . ? C5 N1 Zn1 116.11(13) . . ? C1 N1 Zn1 125.70(16) . . ? C6 N2 C6 120.1(2) . 2_556 ? C6 N2 Zn1 119.94(10) . . ? C6 N2 Zn1 119.94(10) 2_556 . ? N1 C1 C2 122.7(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 118.82(19) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 122.10(17) . . ? N1 C5 C6 114.27(16) . 2_556 ? C4 C5 C6 123.62(17) . 2_556 ? N2 C6 C7 121.28(17) . . ? N2 C6 C5 114.31(15) . 2_556 ? C7 C6 C5 124.40(17) . 2_556 ? C6 C7 C8 119.87(17) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C7 117.6(2) 2_556 . ? C7 C8 C9 121.21(11) 2_556 . ? C7 C8 C9 121.21(11) . . ? C10 C9 C10 117.3(3) 2_556 . ? C10 C9 C8 121.35(14) 2_556 . ? C10 C9 C8 121.35(14) . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C11 118.7(3) . 2_556 ? C11 C12 H12 120.6 . . ? C11 C12 H12 120.6 2_556 . ? O2 C31 O1 124.48(19) . . ? O2 C31 C32 120.25(19) . . ? O1 C31 C32 115.21(17) . . ? C33 C32 C37 118.4(2) . . ? C33 C32 C31 121.53(18) . . ? C37 C32 C31 120.0(2) . . ? C32 C33 C34 120.2(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 120.9(3) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C36 C35 C34 119.6(3) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? C35 C36 C37 120.8(3) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C36 C37 C32 120.1(3) . . ? C36 C37 H37 119.9 . . ? C32 C37 H37 119.9 . . ? 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 O1 Zn1 O1 C31 -167.2(2) 2_556 . . . ? N2 Zn1 O1 C31 12.8(2) . . . . ? N1 Zn1 O1 C31 -69.57(18) 2_556 . . . ? N1 Zn1 O1 C31 87.81(17) . . . . ? O1 Zn1 N1 C5 125.10(13) 2_556 . . . ? O1 Zn1 N1 C5 -135.95(13) . . . . ? N2 Zn1 N1 C5 -4.57(12) . . . . ? N1 Zn1 N1 C5 -4.57(12) 2_556 . . . ? O1 Zn1 N1 C1 -51.4(2) 2_556 . . . ? O1 Zn1 N1 C1 47.5(2) . . . . ? N2 Zn1 N1 C1 178.9(2) . . . . ? N1 Zn1 N1 C1 178.9(2) 2_556 . . . ? O1 Zn1 N2 C6 86.64(10) 2_556 . . . ? O1 Zn1 N2 C6 -93.36(10) . . . . ? N1 Zn1 N2 C6 2.37(9) 2_556 . . . ? N1 Zn1 N2 C6 -177.63(9) . . . . ? O1 Zn1 N2 C6 -93.36(10) 2_556 . . 2_556 ? O1 Zn1 N2 C6 86.64(10) . . . 2_556 ? N1 Zn1 N2 C6 -177.63(9) 2_556 . . 2_556 ? N1 Zn1 N2 C6 2.37(9) . . . 2_556 ? C5 N1 C1 C2 -0.7(4) . . . . ? Zn1 N1 C1 C2 175.7(2) . . . . ? N1 C1 C2 C3 -1.3(5) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C1 N1 C5 C4 2.2(3) . . . . ? Zn1 N1 C5 C4 -174.64(13) . . . . ? C1 N1 C5 C6 -177.30(19) . . . 2_556 ? Zn1 N1 C5 C6 5.91(19) . . . 2_556 ? C3 C4 C5 N1 -1.5(3) . . . . ? C3 C4 C5 C6 177.88(17) . . . 2_556 ? C6 N2 C6 C7 0.51(12) 2_556 . . . ? Zn1 N2 C6 C7 -179.49(12) . . . . ? C6 N2 C6 C5 179.92(15) 2_556 . . 2_556 ? Zn1 N2 C6 C5 -0.08(15) . . . 2_556 ? N2 C6 C7 C8 -1.0(2) . . . . ? C5 C6 C7 C8 179.63(13) 2_556 . . . ? C6 C7 C8 C7 0.49(11) . . . 2_556 ? C6 C7 C8 C9 -179.51(11) . . . . ? C7 C8 C9 C10 -160.67(17) 2_556 . . 2_556 ? C7 C8 C9 C10 19.33(17) . . . 2_556 ? C7 C8 C9 C10 19.33(17) 2_556 . . . ? C7 C8 C9 C10 -160.67(17) . . . . ? C10 C9 C10 C11 0.2(2) 2_556 . . . ? C8 C9 C10 C11 -179.8(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C11 0.2(2) . . . 2_556 ? Zn1 O1 C31 O2 1.0(3) . . . . ? Zn1 O1 C31 C32 178.16(13) . . . . ? O2 C31 C32 C33 -168.5(2) . . . . ? O1 C31 C32 C33 14.2(3) . . . . ? O2 C31 C32 C37 14.4(3) . . . . ? O1 C31 C32 C37 -162.9(2) . . . . ? C37 C32 C33 C34 0.9(4) . . . . ? C31 C32 C33 C34 -176.2(2) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? C33 C34 C35 C36 -0.8(5) . . . . ? C34 C35 C36 C37 0.0(6) . . . . ? C35 C36 C37 C32 1.3(5) . . . . ? C33 C32 C37 C36 -1.7(4) . . . . ? C31 C32 C37 C36 175.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.289 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.048 data_la _database_code_depnum_ccdc_archive 'CCDC 831975' #TrackingRef '2-L.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H29 N3 O6 S2 Zn' _chemical_formula_sum 'C35 H29 N3 O6 S2 Zn' _chemical_formula_weight 717.14 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' S S 0.1246 0.1234 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 20.389(4) _cell_length_b 13.924(3) _cell_length_c 12.196(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.21(3) _cell_angle_gamma 90.00 _cell_volume 3182.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 18521 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 28.39 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.955 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18521 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.39 _reflns_number_total 3968 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0800P)^2^+0.5090P] 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 3968 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.34151(2) 0.2500 0.04353(13) Uani 1 2 d S . . O1 O 0.43993(10) 0.24929(13) 0.2891(2) 0.0775(6) Uani 1 1 d . . . O2 O 0.36183(15) 0.24966(15) 0.39003(19) 0.0921(7) Uani 1 1 d . . . O3 O 0.32582(12) 0.32565(13) 0.1965(2) 0.0804(6) Uani 1 1 d . . . N1 N 0.43635(9) 0.37853(13) 0.06689(16) 0.0456(4) Uani 1 1 d . . . N2 N 0.5000 0.48889(15) 0.2500 0.0395(5) Uani 1 2 d S . . C1 C 0.40550(13) 0.31741(18) -0.0227(2) 0.0569(6) Uani 1 1 d . . . H1 H 0.4117 0.2519 -0.0070 0.068 Uiso 1 1 calc R . . C2 C 0.36503(14) 0.34650(19) -0.1369(2) 0.0620(7) Uani 1 1 d . . . H2 H 0.3443 0.3015 -0.1971 0.074 Uiso 1 1 calc R . . C3 C 0.35562(12) 0.4418(2) -0.1609(2) 0.0607(6) Uani 1 1 d . . . H3 H 0.3286 0.4630 -0.2379 0.073 Uiso 1 1 calc R . . C4 C 0.38686(12) 0.50743(17) -0.0692(2) 0.0510(5) Uani 1 1 d . . . H4 H 0.3810 0.5731 -0.0836 0.061 Uiso 1 1 calc R . . C5 C 0.42687(10) 0.47305(15) 0.04393(18) 0.0424(4) Uani 1 1 d . . . C6 C 0.46321(10) 0.53664(14) 0.14883(18) 0.0405(4) Uani 1 1 d . . . C7 C 0.46144(11) 0.63603(15) 0.1468(2) 0.0466(5) Uani 1 1 d . . . H7 H 0.4345 0.6681 0.0765 0.056 Uiso 1 1 calc R . . C8 C 0.5000 0.6882(2) 0.2500 0.0467(7) Uani 1 2 d S . . C9 C 0.5000 0.7954(2) 0.2500 0.0542(8) Uani 1 2 d S . . C10 C 0.48031(16) 0.84669(16) 0.1441(3) 0.0666(7) Uani 1 1 d . . . H10 H 0.4673 0.8139 0.0722 0.080 Uiso 1 1 calc R . . C11 C 0.47982(15) 0.94633(19) 0.1448(3) 0.0780(8) Uani 1 1 d . . . H11 H 0.4657 0.9797 0.0730 0.094 Uiso 1 1 calc R . . C12 C 0.5000 0.9962(3) 0.2500 0.0801(13) Uani 1 2 d S . . H12 H 0.5000 1.0630 0.2500 0.096 Uiso 1 2 calc SR . . C13 C 0.33223(11) 0.13832(16) 0.2073(2) 0.0466(5) Uani 1 1 d . . . C14 C 0.33926(13) 0.05876(18) 0.2774(2) 0.0566(6) Uani 1 1 d . . . H14 H 0.3584 0.0642 0.3601 0.068 Uiso 1 1 calc R . . C15 C 0.31730(14) -0.03031(18) 0.2231(3) 0.0646(7) Uani 1 1 d . . . H15 H 0.3215 -0.0846 0.2698 0.078 Uiso 1 1 calc R . . C16 C 0.28927(14) -0.03847(19) 0.0997(3) 0.0640(7) Uani 1 1 d . . . C17 C 0.28219(14) 0.0431(2) 0.0319(2) 0.0653(7) Uani 1 1 d . . . H17 H 0.2627 0.0384 -0.0508 0.078 Uiso 1 1 calc R . . C18 C 0.30345(13) 0.13077(19) 0.0845(2) 0.0564(5) Uani 1 1 d . . . H18 H 0.2985 0.1852 0.0376 0.068 Uiso 1 1 calc R . . C19 C 0.2678(2) -0.1356(2) 0.0410(4) 0.0967(12) Uani 1 1 d . . . H19A H 0.2213 -0.1312 -0.0223 0.145 Uiso 1 1 calc R . . H19B H 0.2668 -0.1816 0.0989 0.145 Uiso 1 1 calc R . . H19C H 0.3017 -0.1557 0.0089 0.145 Uiso 1 1 calc R . . S1 S 0.36473(3) 0.25045(4) 0.27500(5) 0.05274(17) 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 0.0508(2) 0.03147(18) 0.0473(2) 0.000 0.01831(16) 0.000 O1 0.0686(11) 0.0577(11) 0.0961(15) 0.0155(9) 0.0218(10) -0.0176(8) O2 0.157(2) 0.0702(13) 0.0631(13) -0.0244(10) 0.0580(14) -0.0369(13) O3 0.0950(14) 0.0504(10) 0.0804(14) -0.0049(9) 0.0181(11) 0.0131(9) N1 0.0533(9) 0.0373(9) 0.0456(10) -0.0028(7) 0.0190(8) -0.0015(7) N2 0.0435(11) 0.0305(11) 0.0442(13) 0.000 0.0172(10) 0.000 C1 0.0695(14) 0.0489(12) 0.0527(14) -0.0097(10) 0.0245(11) -0.0057(11) C2 0.0628(14) 0.0719(18) 0.0493(14) -0.0155(11) 0.0199(11) -0.0076(11) C3 0.0526(12) 0.0796(18) 0.0461(13) -0.0035(11) 0.0154(10) 0.0063(11) C4 0.0530(11) 0.0495(12) 0.0487(12) 0.0066(9) 0.0182(10) 0.0079(9) C5 0.0402(9) 0.0444(10) 0.0455(11) -0.0003(8) 0.0199(8) 0.0012(8) C6 0.0412(9) 0.0377(9) 0.0455(11) 0.0009(8) 0.0203(8) 0.0010(7) C7 0.0486(11) 0.0399(10) 0.0508(12) 0.0057(9) 0.0190(10) 0.0033(8) C8 0.0470(14) 0.0351(13) 0.0610(19) 0.000 0.0246(14) 0.000 C9 0.0507(16) 0.0359(15) 0.075(2) 0.000 0.0236(15) 0.000 C10 0.0754(16) 0.0396(12) 0.0823(19) 0.0059(11) 0.0286(15) -0.0046(10) C11 0.0783(17) 0.0452(14) 0.108(2) 0.0175(14) 0.0346(17) 0.0010(12) C12 0.070(2) 0.0352(17) 0.140(4) 0.000 0.046(3) 0.000 C13 0.0469(10) 0.0447(11) 0.0489(12) -0.0085(9) 0.0195(9) -0.0045(8) C14 0.0622(13) 0.0510(13) 0.0527(13) -0.0010(10) 0.0185(11) -0.0042(10) C15 0.0711(15) 0.0430(12) 0.085(2) -0.0028(12) 0.0361(14) -0.0029(11) C16 0.0627(14) 0.0551(14) 0.0845(19) -0.0272(13) 0.0400(13) -0.0134(11) C17 0.0681(15) 0.0728(17) 0.0564(14) -0.0212(13) 0.0262(12) -0.0107(12) C18 0.0643(14) 0.0570(13) 0.0494(13) -0.0061(10) 0.0239(11) -0.0048(11) C19 0.106(3) 0.0664(18) 0.135(3) -0.047(2) 0.066(2) -0.0268(17) S1 0.0663(3) 0.0437(3) 0.0473(3) -0.0058(2) 0.0213(3) -0.0109(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9586(17) 2_655 ? Zn1 O1 1.9586(17) . ? Zn1 N2 2.052(2) . ? Zn1 N1 2.1570(19) . ? Zn1 N1 2.1570(19) 2_655 ? O1 S1 1.474(2) . ? O2 S1 1.427(2) . ? O3 S1 1.429(2) . ? N1 C1 1.331(3) . ? N1 C5 1.344(3) . ? N2 C6 1.341(2) . ? N2 C6 1.341(2) 2_655 ? C1 C2 1.371(4) . ? C1 H1 0.9300 . ? C2 C3 1.357(4) . ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 C6 1.491(3) . ? C6 C7 1.384(3) . ? C7 C8 1.397(3) . ? C7 H7 0.9300 . ? C8 C7 1.397(3) 2_655 ? C8 C9 1.493(4) . ? C9 C10 1.389(3) . ? C9 C10 1.389(3) 2_655 ? C10 C11 1.387(3) . ? C10 H10 0.9300 . ? C11 C12 1.372(4) . ? C11 H11 0.9300 . ? C12 C11 1.372(4) 2_655 ? C12 H12 0.9300 . ? C13 C14 1.372(3) . ? C13 C18 1.381(3) . ? C13 S1 1.768(2) . ? C14 C15 1.394(3) . ? C14 H14 0.9300 . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 C17 1.379(4) . ? C16 C19 1.512(4) . ? C17 C18 1.368(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 98.07(13) 2_655 . ? O1 Zn1 N2 130.96(6) 2_655 . ? O1 Zn1 N2 130.96(6) . . ? O1 Zn1 N1 94.79(8) 2_655 . ? O1 Zn1 N1 103.28(8) . . ? N2 Zn1 N1 76.17(5) . . ? O1 Zn1 N1 103.28(8) 2_655 2_655 ? O1 Zn1 N1 94.79(8) . 2_655 ? N2 Zn1 N1 76.17(5) . 2_655 ? N1 Zn1 N1 152.35(10) . 2_655 ? S1 O1 Zn1 133.31(12) . . ? C1 N1 C5 118.2(2) . . ? C1 N1 Zn1 126.43(16) . . ? C5 N1 Zn1 115.36(14) . . ? C6 N2 C6 120.5(2) . 2_655 ? C6 N2 Zn1 119.73(12) . . ? C6 N2 Zn1 119.73(12) 2_655 . ? N1 C1 C2 123.1(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.0(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.81(19) . . ? N1 C5 C6 114.88(18) . . ? C4 C5 C6 123.3(2) . . ? N2 C6 C7 120.90(19) . . ? N2 C6 C5 113.82(18) . . ? C7 C6 C5 125.28(19) . . ? C6 C7 C8 120.2(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C7 117.3(3) . 2_655 ? C7 C8 C9 121.34(14) . . ? C7 C8 C9 121.34(14) 2_655 . ? C10 C9 C10 118.1(3) . 2_655 ? C10 C9 C8 120.93(16) . . ? C10 C9 C8 120.93(16) 2_655 . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C11 119.2(4) . 2_655 ? C11 C12 H12 120.4 . . ? C11 C12 H12 120.4 2_655 . ? C14 C13 C18 120.7(2) . . ? C14 C13 S1 119.62(18) . . ? C18 C13 S1 119.64(18) . . ? C13 C14 C15 119.2(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.4(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.0(2) . . ? C17 C16 C19 120.7(3) . . ? C15 C16 C19 120.4(3) . . ? C18 C17 C16 121.0(2) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C13 119.8(2) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 S1 O3 115.90(15) . . ? O2 S1 O1 109.25(15) . . ? O3 S1 O1 111.30(13) . . ? O2 S1 C13 107.39(11) . . ? O3 S1 C13 109.09(12) . . ? O1 S1 C13 103.06(11) . . ? 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 O1 Zn1 O1 S1 -147.0(2) 2_655 . . . ? N2 Zn1 O1 S1 33.0(2) . . . . ? N1 Zn1 O1 S1 -50.1(2) . . . . ? N1 Zn1 O1 S1 108.86(19) 2_655 . . . ? O1 Zn1 N1 C1 48.6(2) 2_655 . . . ? O1 Zn1 N1 C1 -50.8(2) . . . . ? N2 Zn1 N1 C1 179.69(19) . . . . ? N1 Zn1 N1 C1 179.69(19) 2_655 . . . ? O1 Zn1 N1 C5 -132.47(15) 2_655 . . . ? O1 Zn1 N1 C5 128.05(15) . . . . ? N2 Zn1 N1 C5 -1.41(13) . . . . ? N1 Zn1 N1 C5 -1.41(13) 2_655 . . . ? O1 Zn1 N2 C6 85.87(12) 2_655 . . . ? O1 Zn1 N2 C6 -94.13(12) . . . . ? N1 Zn1 N2 C6 1.59(10) . . . . ? N1 Zn1 N2 C6 -178.41(10) 2_655 . . . ? O1 Zn1 N2 C6 -94.13(12) 2_655 . . 2_655 ? O1 Zn1 N2 C6 85.87(12) . . . 2_655 ? N1 Zn1 N2 C6 -178.41(10) . . . 2_655 ? N1 Zn1 N2 C6 1.59(10) 2_655 . . 2_655 ? C5 N1 C1 C2 0.4(3) . . . . ? Zn1 N1 C1 C2 179.28(18) . . . . ? N1 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C1 N1 C5 C4 -0.5(3) . . . . ? Zn1 N1 C5 C4 -179.52(15) . . . . ? C1 N1 C5 C6 -179.91(18) . . . . ? Zn1 N1 C5 C6 1.1(2) . . . . ? C3 C4 C5 N1 0.2(3) . . . . ? C3 C4 C5 C6 179.56(19) . . . . ? C6 N2 C6 C7 -0.98(14) 2_655 . . . ? Zn1 N2 C6 C7 179.02(14) . . . . ? C6 N2 C6 C5 178.50(17) 2_655 . . . ? Zn1 N2 C6 C5 -1.50(17) . . . . ? N1 C5 C6 N2 0.2(2) . . . . ? C4 C5 C6 N2 -179.19(17) . . . . ? N1 C5 C6 C7 179.65(19) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? N2 C6 C7 C8 2.0(3) . . . . ? C5 C6 C7 C8 -177.46(15) . . . . ? C6 C7 C8 C7 -0.95(13) . . . 2_655 ? C6 C7 C8 C9 179.05(13) . . . . ? C7 C8 C9 C10 -19.24(18) . . . . ? C7 C8 C9 C10 160.76(18) 2_655 . . . ? C7 C8 C9 C10 160.76(18) . . . 2_655 ? C7 C8 C9 C10 -19.24(18) 2_655 . . 2_655 ? C10 C9 C10 C11 -0.6(2) 2_655 . . . ? C8 C9 C10 C11 179.4(2) . . . . ? C9 C10 C11 C12 1.2(4) . . . . ? C10 C11 C12 C11 -0.6(2) . . . 2_655 ? C18 C13 C14 C15 0.3(4) . . . . ? S1 C13 C14 C15 -176.24(19) . . . . ? C13 C14 C15 C16 0.6(4) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C14 C15 C16 C19 177.9(3) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? C19 C16 C17 C18 -178.1(3) . . . . ? C16 C17 C18 C13 -0.3(4) . . . . ? C14 C13 C18 C17 -0.5(4) . . . . ? S1 C13 C18 C17 176.08(19) . . . . ? Zn1 O1 S1 O2 -115.00(19) . . . . ? Zn1 O1 S1 O3 14.2(2) . . . . ? Zn1 O1 S1 C13 131.05(18) . . . . ? C14 C13 S1 O2 -28.1(2) . . . . ? C18 C13 S1 O2 155.3(2) . . . . ? C14 C13 S1 O3 -154.5(2) . . . . ? C18 C13 S1 O3 28.9(2) . . . . ? C14 C13 S1 O1 87.2(2) . . . . ? C18 C13 S1 O1 -89.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.755 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.055 data_m _database_code_depnum_ccdc_archive 'CCDC 831976' #TrackingRef '1-M.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 F6 N3 O7 S2 Zn' _chemical_formula_sum 'C23 H17 F6 N3 O7 S2 Zn' _chemical_formula_weight 690.93 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0686(7) _cell_length_b 22.0148(13) _cell_length_c 12.9592(9) _cell_angle_alpha 90.00 _cell_angle_beta 117.908(4) _cell_angle_gamma 90.00 _cell_volume 2790.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 33615 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 28.31 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.611 _exptl_absorpt_correction_T_max 0.723 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33615 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6919 _reflns_number_gt 5801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0497P)^2^+3.4990P] 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 6919 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 -0.22130(2) -0.092575(10) 0.22670(2) 0.02231(8) Uani 1 1 d . . . S1 S 0.05188(6) -0.10502(2) 0.49674(5) 0.02584(12) Uani 1 1 d . . . S2 S -0.49836(5) -0.11162(2) -0.03454(4) 0.02325(11) Uani 1 1 d . . . F1 F 0.2636(3) -0.1169(2) 0.4655(4) 0.170(2) Uani 1 1 d . . . F2 F 0.2680(2) -0.17332(13) 0.5991(2) 0.0984(9) Uani 1 1 d . . . F3 F 0.1346(4) -0.19624(14) 0.4213(3) 0.1243(13) Uani 1 1 d . . . F4 F -0.7288(2) -0.17088(13) -0.1126(2) 0.0976(9) Uani 1 1 d . . . F5 F -0.5990(2) -0.18065(12) 0.0704(2) 0.0878(8) Uani 1 1 d . . . F6 F -0.7099(2) -0.09726(12) 0.0007(2) 0.0862(8) Uani 1 1 d . . . O1 O -0.01971(16) -0.08317(7) 0.37748(13) 0.0287(3) Uani 1 1 d . . . O2 O 0.1233(3) -0.05805(11) 0.5784(2) 0.0845(10) Uani 1 1 d . . . O3 O -0.0216(2) -0.14709(11) 0.52910(19) 0.0566(6) Uani 1 1 d . . . O4 O -0.42031(17) -0.08065(7) 0.07588(14) 0.0321(3) Uani 1 1 d . . . O5 O -0.43235(19) -0.16409(8) -0.05082(16) 0.0383(4) Uani 1 1 d . . . O6 O -0.56160(17) -0.07162(8) -0.13354(14) 0.0332(4) Uani 1 1 d . . . O7 O -0.21383(15) -0.00175(7) 0.21932(13) 0.0289(3) Uani 1 1 d . . . H7C H -0.1849 0.0124 0.2852 0.035 Uiso 1 1 d R . . H7D H -0.2888 0.0166 0.1809 0.035 Uiso 1 1 d R . . N1 N -0.32167(18) -0.11153(8) 0.33068(15) 0.0229(3) Uani 1 1 d . . . N2 N -0.22402(16) -0.18559(8) 0.23057(14) 0.0206(3) Uani 1 1 d . . . N3 N -0.12085(18) -0.11863(8) 0.12587(15) 0.0234(3) Uani 1 1 d . . . C1 C -0.3676(2) -0.07096(10) 0.3808(2) 0.0287(4) Uani 1 1 d . . . H1 H -0.3509 -0.0300 0.3756 0.034 Uiso 1 1 calc R . . C01 C 0.1885(4) -0.14946(18) 0.4960(4) 0.0666(11) Uani 1 1 d . . . C2 C -0.4389(3) -0.08756(11) 0.4400(2) 0.0324(5) Uani 1 1 d . . . H2 H -0.4692 -0.0583 0.4743 0.039 Uiso 1 1 calc R . . C02 C -0.6421(3) -0.14188(16) -0.0184(3) 0.0541(8) Uani 1 1 d . . . C3 C -0.4644(2) -0.14834(11) 0.4473(2) 0.0315(5) Uani 1 1 d . . . H3 H -0.5132 -0.1605 0.4858 0.038 Uiso 1 1 calc R . . C4 C -0.4165(2) -0.19119(10) 0.3964(2) 0.0277(4) Uani 1 1 d . . . H4 H -0.4325 -0.2324 0.4004 0.033 Uiso 1 1 calc R . . C5 C -0.3444(2) -0.17114(9) 0.33954(17) 0.0213(4) Uani 1 1 d . . . C6 C -0.2860(2) -0.21347(9) 0.28436(17) 0.0207(4) Uani 1 1 d . . . C7 C -0.2911(2) -0.27631(9) 0.28840(18) 0.0230(4) Uani 1 1 d . . . H7 H -0.3334 -0.2952 0.3272 0.028 Uiso 1 1 calc R . . C8 C -0.2316(2) -0.31112(9) 0.23314(18) 0.0233(4) Uani 1 1 d . . . C9 C -0.1678(2) -0.28030(9) 0.17676(18) 0.0242(4) Uani 1 1 d . . . H9 H -0.1276 -0.3019 0.1391 0.029 Uiso 1 1 calc R . . C10 C -0.1655(2) -0.21751(9) 0.17789(17) 0.0214(4) Uani 1 1 d . . . C11 C -0.1017(2) -0.17892(10) 0.12189(18) 0.0232(4) Uani 1 1 d . . . C12 C -0.0280(2) -0.20262(11) 0.0690(2) 0.0306(5) Uani 1 1 d . . . H12 H -0.0148 -0.2443 0.0679 0.037 Uiso 1 1 calc R . . C13 C 0.0257(3) -0.16285(12) 0.0179(2) 0.0368(5) Uani 1 1 d . . . H13 H 0.0750 -0.1777 -0.0183 0.044 Uiso 1 1 calc R . . C14 C 0.0053(3) -0.10120(12) 0.0211(2) 0.0361(5) Uani 1 1 d . . . H14 H 0.0405 -0.0739 -0.0128 0.043 Uiso 1 1 calc R . . C15 C -0.0685(2) -0.08081(11) 0.0758(2) 0.0294(4) Uani 1 1 d . . . H15 H -0.0823 -0.0393 0.0780 0.035 Uiso 1 1 calc R . . C16 C -0.2365(2) -0.37844(10) 0.23416(18) 0.0253(4) Uani 1 1 d . . . C17 C -0.1470(2) -0.41362(10) 0.2100(2) 0.0310(5) Uani 1 1 d . . . H17 H -0.0830 -0.3945 0.1936 0.037 Uiso 1 1 calc R . . C18 C -0.1530(3) -0.47659(11) 0.2103(2) 0.0365(5) Uani 1 1 d . . . H18 H -0.0943 -0.4994 0.1926 0.044 Uiso 1 1 calc R . . C19 C -0.2462(3) -0.50573(11) 0.2369(2) 0.0384(6) Uani 1 1 d . . . H19 H -0.2496 -0.5479 0.2377 0.046 Uiso 1 1 calc R . . C20 C -0.3346(3) -0.47152(11) 0.2623(2) 0.0355(5) Uani 1 1 d . . . H20 H -0.3964 -0.4909 0.2811 0.043 Uiso 1 1 calc R . . C21 C -0.3307(2) -0.40850(10) 0.2596(2) 0.0296(5) Uani 1 1 d . . . H21 H -0.3916 -0.3860 0.2749 0.036 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 0.02629(13) 0.01780(12) 0.02667(13) 0.00043(8) 0.01558(10) 0.00025(9) S1 0.0270(3) 0.0253(3) 0.0248(2) 0.00167(19) 0.0118(2) 0.0050(2) S2 0.0215(2) 0.0213(2) 0.0274(2) -0.00114(18) 0.0118(2) 0.00129(18) F1 0.0861(19) 0.224(4) 0.262(5) 0.155(4) 0.134(3) 0.084(2) F2 0.0605(13) 0.1038(19) 0.114(2) 0.0546(16) 0.0264(14) 0.0515(14) F3 0.179(3) 0.103(2) 0.106(2) 0.0029(17) 0.079(2) 0.089(2) F4 0.0555(13) 0.114(2) 0.0995(18) -0.0067(15) 0.0160(13) -0.0526(14) F5 0.0729(14) 0.0956(17) 0.1000(17) 0.0474(14) 0.0448(13) -0.0138(13) F6 0.0562(12) 0.111(2) 0.123(2) 0.0248(15) 0.0687(14) 0.0177(12) O1 0.0277(8) 0.0298(8) 0.0277(8) 0.0042(6) 0.0121(6) -0.0031(6) O2 0.110(2) 0.0490(13) 0.0395(12) -0.0166(10) -0.0113(13) 0.0094(14) O3 0.0443(11) 0.0746(15) 0.0590(13) 0.0375(11) 0.0309(10) 0.0079(10) O4 0.0300(8) 0.0297(8) 0.0314(8) -0.0054(6) 0.0101(7) 0.0053(6) O5 0.0422(10) 0.0268(8) 0.0425(10) -0.0063(7) 0.0169(8) 0.0098(7) O6 0.0330(9) 0.0356(9) 0.0315(8) 0.0057(7) 0.0155(7) 0.0099(7) O7 0.0292(8) 0.0204(7) 0.0301(8) 0.0010(6) 0.0078(6) 0.0026(6) N1 0.0248(8) 0.0215(8) 0.0251(8) 0.0000(6) 0.0140(7) 0.0025(7) N2 0.0207(8) 0.0201(8) 0.0234(8) 0.0003(6) 0.0125(7) 0.0009(6) N3 0.0242(8) 0.0232(8) 0.0252(8) 0.0005(7) 0.0135(7) -0.0027(7) C1 0.0335(11) 0.0215(10) 0.0342(11) -0.0015(8) 0.0185(10) 0.0050(8) C01 0.0527(19) 0.074(2) 0.088(3) 0.036(2) 0.0454(19) 0.0357(18) C2 0.0365(12) 0.0319(12) 0.0352(12) -0.0020(9) 0.0221(10) 0.0095(9) C02 0.0365(15) 0.0622(19) 0.066(2) 0.0139(16) 0.0261(14) -0.0099(14) C3 0.0349(12) 0.0341(12) 0.0363(12) 0.0044(9) 0.0256(10) 0.0062(9) C4 0.0304(11) 0.0263(10) 0.0343(11) 0.0038(8) 0.0217(10) 0.0038(8) C5 0.0233(9) 0.0196(9) 0.0232(9) 0.0003(7) 0.0127(8) 0.0026(7) C6 0.0207(9) 0.0210(9) 0.0230(9) -0.0007(7) 0.0123(8) 0.0010(7) C7 0.0234(10) 0.0220(10) 0.0281(10) 0.0017(7) 0.0158(8) 0.0010(7) C8 0.0244(10) 0.0212(10) 0.0262(10) -0.0014(7) 0.0133(8) 0.0012(7) C9 0.0249(10) 0.0236(10) 0.0281(10) -0.0027(8) 0.0158(8) 0.0021(8) C10 0.0208(9) 0.0236(9) 0.0230(9) -0.0009(7) 0.0130(8) -0.0002(7) C11 0.0212(9) 0.0263(10) 0.0236(9) -0.0017(8) 0.0117(8) -0.0030(8) C12 0.0320(11) 0.0307(11) 0.0373(12) -0.0040(9) 0.0231(10) -0.0029(9) C13 0.0389(13) 0.0453(14) 0.0411(13) -0.0065(11) 0.0310(11) -0.0068(11) C14 0.0388(13) 0.0427(14) 0.0358(12) 0.0010(10) 0.0249(11) -0.0099(10) C15 0.0326(11) 0.0282(11) 0.0305(11) 0.0025(8) 0.0173(9) -0.0051(9) C16 0.0290(10) 0.0202(10) 0.0282(10) -0.0013(8) 0.0146(9) 0.0024(8) C17 0.0330(12) 0.0265(11) 0.0369(12) -0.0015(9) 0.0192(10) 0.0043(9) C18 0.0375(13) 0.0259(11) 0.0444(14) -0.0032(10) 0.0176(11) 0.0089(9) C19 0.0431(14) 0.0192(10) 0.0477(14) -0.0032(9) 0.0169(12) 0.0006(9) C20 0.0371(13) 0.0253(11) 0.0458(14) -0.0017(10) 0.0208(11) -0.0044(9) C21 0.0336(12) 0.0227(10) 0.0372(12) -0.0037(8) 0.0205(10) -0.0007(8) _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 2.0054(15) . ? Zn1 N2 2.0488(17) . ? Zn1 N1 2.1506(17) . ? Zn1 N3 2.1524(18) . ? Zn1 O4 2.1705(16) . ? Zn1 O1 2.1814(16) . ? S1 O3 1.4190(19) . ? S1 O2 1.425(2) . ? S1 O1 1.4497(16) . ? S1 C01 1.805(3) . ? S2 O5 1.4341(16) . ? S2 O6 1.4389(17) . ? S2 O4 1.4496(16) . ? S2 C02 1.825(3) . ? F1 C01 1.292(4) . ? F2 C01 1.317(4) . ? F3 C01 1.346(5) . ? F4 C02 1.312(4) . ? F5 C02 1.328(4) . ? F6 C02 1.328(4) . ? O7 H7C 0.8199 . ? O7 H7D 0.8440 . ? N1 C1 1.337(3) . ? N1 C5 1.351(3) . ? N2 C6 1.335(2) . ? N2 C10 1.339(2) . ? N3 C15 1.343(3) . ? N3 C11 1.349(3) . ? C1 C2 1.383(3) . ? C1 H1 0.9300 . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.390(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 C6 1.493(3) . ? C6 C7 1.387(3) . ? C7 C8 1.406(3) . ? C7 H7 0.9300 . ? C8 C9 1.405(3) . ? C8 C16 1.483(3) . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 C11 1.492(3) . ? C11 C12 1.390(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9300 . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 C15 1.382(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.399(3) . ? C16 C17 1.403(3) . ? C17 C18 1.388(3) . ? C17 H17 0.9300 . ? C18 C19 1.388(4) . ? C18 H18 0.9300 . ? C19 C20 1.391(4) . ? C19 H19 0.9300 . ? C20 C21 1.389(3) . ? C20 H20 0.9300 . ? C21 H21 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 N2 177.55(6) . . ? O7 Zn1 N1 105.57(7) . . ? N2 Zn1 N1 76.87(6) . . ? O7 Zn1 N3 101.08(7) . . ? N2 Zn1 N3 76.48(6) . . ? N1 Zn1 N3 153.35(7) . . ? O7 Zn1 O4 83.32(6) . . ? N2 Zn1 O4 97.04(6) . . ? N1 Zn1 O4 89.06(7) . . ? N3 Zn1 O4 94.61(6) . . ? O7 Zn1 O1 84.28(6) . . ? N2 Zn1 O1 95.37(6) . . ? N1 Zn1 O1 93.96(6) . . ? N3 Zn1 O1 88.09(6) . . ? O4 Zn1 O1 167.59(6) . . ? O3 S1 O2 116.74(18) . . ? O3 S1 O1 115.39(11) . . ? O2 S1 O1 112.77(13) . . ? O3 S1 C01 104.19(16) . . ? O2 S1 C01 102.8(2) . . ? O1 S1 C01 102.43(14) . . ? O5 S2 O6 115.50(11) . . ? O5 S2 O4 114.50(10) . . ? O6 S2 O4 114.13(10) . . ? O5 S2 C02 104.72(14) . . ? O6 S2 C02 103.85(13) . . ? O4 S2 C02 101.95(14) . . ? S1 O1 Zn1 137.99(10) . . ? S2 O4 Zn1 135.79(10) . . ? Zn1 O7 H7C 109.5 . . ? Zn1 O7 H7D 117.0 . . ? H7C O7 H7D 103.3 . . ? C1 N1 C5 118.66(18) . . ? C1 N1 Zn1 126.88(15) . . ? C5 N1 Zn1 114.38(13) . . ? C6 N2 C10 120.97(18) . . ? C6 N2 Zn1 119.30(13) . . ? C10 N2 Zn1 119.73(13) . . ? C15 N3 C11 118.73(19) . . ? C15 N3 Zn1 126.22(15) . . ? C11 N3 Zn1 114.86(13) . . ? N1 C1 C2 122.6(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? F1 C01 F2 108.1(3) . . ? F1 C01 F3 109.7(4) . . ? F2 C01 F3 106.6(3) . . ? F1 C01 S1 111.2(3) . . ? F2 C01 S1 112.0(3) . . ? F3 C01 S1 109.2(3) . . ? C3 C2 C1 118.8(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? F4 C02 F6 107.6(3) . . ? F4 C02 F5 107.6(3) . . ? F6 C02 F5 108.6(3) . . ? F4 C02 S2 111.6(2) . . ? F6 C02 S2 110.5(2) . . ? F5 C02 S2 110.8(2) . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 122.00(18) . . ? N1 C5 C6 115.24(17) . . ? C4 C5 C6 122.76(18) . . ? N2 C6 C7 121.21(18) . . ? N2 C6 C5 113.99(17) . . ? C7 C6 C5 124.80(18) . . ? C6 C7 C8 119.21(19) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C9 118.09(19) . . ? C7 C8 C16 120.81(18) . . ? C9 C8 C16 121.10(18) . . ? C10 C9 C8 119.24(18) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N2 C10 C9 121.28(18) . . ? N2 C10 C11 113.63(17) . . ? C9 C10 C11 125.08(18) . . ? N3 C11 C12 121.82(19) . . ? N3 C11 C10 115.04(17) . . ? C12 C11 C10 123.14(19) . . ? C13 C12 C11 118.6(2) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C14 C13 C12 119.6(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 118.6(2) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N3 C15 C14 122.6(2) . . ? N3 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C21 C16 C17 118.3(2) . . ? C21 C16 C8 120.63(19) . . ? C17 C16 C8 121.12(19) . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 120.3(2) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.7(2) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 120.1(2) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 120.9(2) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 O1 Zn1 4.0(2) . . . . ? O2 S1 O1 Zn1 -133.6(2) . . . . ? C01 S1 O1 Zn1 116.5(2) . . . . ? O7 Zn1 O1 S1 131.54(16) . . . . ? N2 Zn1 O1 S1 -50.90(16) . . . . ? N1 Zn1 O1 S1 26.27(16) . . . . ? N3 Zn1 O1 S1 -127.12(16) . . . . ? O4 Zn1 O1 S1 130.0(2) . . . . ? O5 S2 O4 Zn1 1.4(2) . . . . ? O6 S2 O4 Zn1 -134.87(14) . . . . ? C02 S2 O4 Zn1 113.85(18) . . . . ? O7 Zn1 O4 S2 139.16(16) . . . . ? N2 Zn1 O4 S2 -38.39(16) . . . . ? N1 Zn1 O4 S2 -115.04(16) . . . . ? N3 Zn1 O4 S2 38.52(16) . . . . ? O1 Zn1 O4 S2 140.7(2) . . . . ? O7 Zn1 N1 C1 -0.8(2) . . . . ? N2 Zn1 N1 C1 179.00(19) . . . . ? N3 Zn1 N1 C1 178.03(17) . . . . ? O4 Zn1 N1 C1 -83.55(18) . . . . ? O1 Zn1 N1 C1 84.40(19) . . . . ? O7 Zn1 N1 C5 175.95(14) . . . . ? N2 Zn1 N1 C5 -4.29(14) . . . . ? N3 Zn1 N1 C5 -5.3(2) . . . . ? O4 Zn1 N1 C5 93.16(15) . . . . ? O1 Zn1 N1 C5 -98.89(15) . . . . ? O7 Zn1 N2 C6 177.6(15) . . . . ? N1 Zn1 N2 C6 3.16(14) . . . . ? N3 Zn1 N2 C6 -177.29(16) . . . . ? O4 Zn1 N2 C6 -84.21(15) . . . . ? O1 Zn1 N2 C6 95.99(15) . . . . ? O7 Zn1 N2 C10 -3.3(16) . . . . ? N1 Zn1 N2 C10 -177.79(16) . . . . ? N3 Zn1 N2 C10 1.77(15) . . . . ? O4 Zn1 N2 C10 94.84(15) . . . . ? O1 Zn1 N2 C10 -84.96(15) . . . . ? O7 Zn1 N3 C15 0.80(19) . . . . ? N2 Zn1 N3 C15 -178.98(19) . . . . ? N1 Zn1 N3 C15 -178.01(17) . . . . ? O4 Zn1 N3 C15 84.88(18) . . . . ? O1 Zn1 N3 C15 -82.99(18) . . . . ? O7 Zn1 N3 C11 175.60(14) . . . . ? N2 Zn1 N3 C11 -4.17(14) . . . . ? N1 Zn1 N3 C11 -3.2(2) . . . . ? O4 Zn1 N3 C11 -100.32(15) . . . . ? O1 Zn1 N3 C11 91.81(15) . . . . ? C5 N1 C1 C2 -0.9(3) . . . . ? Zn1 N1 C1 C2 175.71(17) . . . . ? O3 S1 C01 F1 178.8(4) . . . . ? O2 S1 C01 F1 -58.9(4) . . . . ? O1 S1 C01 F1 58.2(4) . . . . ? O3 S1 C01 F2 -60.1(3) . . . . ? O2 S1 C01 F2 62.2(3) . . . . ? O1 S1 C01 F2 179.4(3) . . . . ? O3 S1 C01 F3 57.7(3) . . . . ? O2 S1 C01 F3 179.9(3) . . . . ? O1 S1 C01 F3 -62.9(3) . . . . ? N1 C1 C2 C3 -0.3(4) . . . . ? O5 S2 C02 F4 -62.1(3) . . . . ? O6 S2 C02 F4 59.5(3) . . . . ? O4 S2 C02 F4 178.3(2) . . . . ? O5 S2 C02 F6 178.3(2) . . . . ? O6 S2 C02 F6 -60.2(3) . . . . ? O4 S2 C02 F6 58.7(3) . . . . ? O5 S2 C02 F5 57.8(3) . . . . ? O6 S2 C02 F5 179.4(3) . . . . ? O4 S2 C02 F5 -61.8(3) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C1 N1 C5 C4 1.6(3) . . . . ? Zn1 N1 C5 C4 -175.38(16) . . . . ? C1 N1 C5 C6 -178.19(18) . . . . ? Zn1 N1 C5 C6 4.8(2) . . . . ? C3 C4 C5 N1 -1.1(3) . . . . ? C3 C4 C5 C6 178.6(2) . . . . ? C10 N2 C6 C7 0.5(3) . . . . ? Zn1 N2 C6 C7 179.57(15) . . . . ? C10 N2 C6 C5 179.36(17) . . . . ? Zn1 N2 C6 C5 -1.6(2) . . . . ? N1 C5 C6 N2 -2.3(3) . . . . ? C4 C5 C6 N2 177.9(2) . . . . ? N1 C5 C6 C7 176.49(19) . . . . ? C4 C5 C6 C7 -3.3(3) . . . . ? N2 C6 C7 C8 -1.0(3) . . . . ? C5 C6 C7 C8 -179.71(19) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C6 C7 C8 C16 -179.17(19) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C16 C8 C9 C10 179.99(19) . . . . ? C6 N2 C10 C9 0.3(3) . . . . ? Zn1 N2 C10 C9 -178.70(15) . . . . ? C6 N2 C10 C11 179.72(17) . . . . ? Zn1 N2 C10 C11 0.7(2) . . . . ? C8 C9 C10 N2 -0.7(3) . . . . ? C8 C9 C10 C11 180.00(19) . . . . ? C15 N3 C11 C12 0.9(3) . . . . ? Zn1 N3 C11 C12 -174.29(17) . . . . ? C15 N3 C11 C10 -178.98(18) . . . . ? Zn1 N3 C11 C10 5.8(2) . . . . ? N2 C10 C11 N3 -4.4(3) . . . . ? C9 C10 C11 N3 175.0(2) . . . . ? N2 C10 C11 C12 175.7(2) . . . . ? C9 C10 C11 C12 -4.9(3) . . . . ? N3 C11 C12 C13 -0.8(3) . . . . ? C10 C11 C12 C13 179.1(2) . . . . ? C11 C12 C13 C14 0.3(4) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C11 N3 C15 C14 -0.5(3) . . . . ? Zn1 N3 C15 C14 174.08(18) . . . . ? C13 C14 C15 N3 0.1(4) . . . . ? C7 C8 C16 C21 18.2(3) . . . . ? C9 C8 C16 C21 -161.6(2) . . . . ? C7 C8 C16 C17 -161.7(2) . . . . ? C9 C8 C16 C17 18.5(3) . . . . ? C21 C16 C17 C18 0.6(3) . . . . ? C8 C16 C17 C18 -179.5(2) . . . . ? C16 C17 C18 C19 -1.3(4) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? C19 C20 C21 C16 -1.5(4) . . . . ? C17 C16 C21 C20 0.8(3) . . . . ? C8 C16 C21 C20 -179.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.819 _refine_diff_density_min -0.775 _refine_diff_density_rms 0.068 data_z _database_code_depnum_ccdc_archive 'CCDC 916058' #TrackingRef '4-Z.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H29 N3 O7 Zn' _chemical_formula_sum 'C36 H29 N3 O7 Zn' _chemical_formula_weight 681.01 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.007(3) _cell_length_b 9.863(2) _cell_length_c 26.388(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.93(3) _cell_angle_gamma 90.00 _cell_volume 3161.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 32635 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.21 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_T_max 0.812 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32635 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.21 _reflns_number_total 6956 _reflns_number_gt 5248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0588P)^2^+2.1952P] 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 6956 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.24908(2) 0.19580(3) 0.366957(11) 0.03946(11) Uani 1 1 d . . . O1 O 0.25675(16) 0.0372(2) 0.32224(8) 0.0538(5) Uani 1 1 d . . . O2 O 0.43219(17) 0.0889(2) 0.34413(8) 0.0551(5) Uani 1 1 d . . . O3 O 0.37304(18) -0.3220(2) 0.15190(8) 0.0626(6) Uani 1 1 d . . . H3A H 0.4369 -0.3433 0.1569 0.094 Uiso 1 1 calc R . . O4 O 0.11069(15) 0.1560(2) 0.37974(8) 0.0500(5) Uani 1 1 d . . . O5 O 0.14289(19) 0.3643(3) 0.40912(11) 0.0744(7) Uani 1 1 d . . . O6 O -0.22882(19) 0.2042(2) 0.49982(10) 0.0676(6) Uani 1 1 d . . . H6A H -0.2209 0.2641 0.5224 0.101 Uiso 1 1 calc R . . O20 O 0.2232(2) 0.6130(3) 0.42535(11) 0.0833(8) Uani 1 1 d . . . H20D H 0.1973 0.5334 0.4178 0.120(18) Uiso 1 1 d R . . N1 N 0.35989(16) 0.1628(2) 0.44947(8) 0.0365(4) Uani 1 1 d . . . N2 N 0.36545(15) 0.3495(2) 0.38083(7) 0.0327(4) Uani 1 1 d . . . N3 N 0.18434(18) 0.3320(2) 0.29655(9) 0.0493(6) Uani 1 1 d . . . C1 C 0.3458(2) 0.0742(3) 0.48442(10) 0.0438(6) Uani 1 1 d . . . H1 H 0.2855 0.0162 0.4725 0.053 Uiso 1 1 calc R . . C2 C 0.4164(2) 0.0646(3) 0.53730(11) 0.0476(6) Uani 1 1 d . . . H2 H 0.4044 0.0011 0.5606 0.057 Uiso 1 1 calc R . . C02 C 0.1652(7) 0.6846(6) 0.3763(2) 0.162(3) Uani 1 1 d . . . H02A H 0.2053 0.7650 0.3744 0.243 Uiso 1 1 calc R . . H02B H 0.0935 0.7094 0.3758 0.243 Uiso 1 1 calc R . . H02C H 0.1578 0.6276 0.3457 0.243 Uiso 1 1 calc R . . C3 C 0.5044(2) 0.1501(3) 0.55498(10) 0.0487(7) Uani 1 1 d . . . H3 H 0.5533 0.1454 0.5906 0.058 Uiso 1 1 calc R . . C4 C 0.5204(2) 0.2438(3) 0.51955(10) 0.0408(5) Uani 1 1 d . . . H4 H 0.5798 0.3033 0.5311 0.049 Uiso 1 1 calc R . . C5 C 0.44695(19) 0.2474(3) 0.46690(9) 0.0342(5) Uani 1 1 d . . . C6 C 0.45429(18) 0.3451(2) 0.42548(9) 0.0326(5) Uani 1 1 d . . . C7 C 0.54490(19) 0.4260(3) 0.43127(9) 0.0360(5) Uani 1 1 d . . . H7 H 0.6068 0.4219 0.4629 0.043 Uiso 1 1 calc R . . C8 C 0.54276(18) 0.5136(2) 0.38937(9) 0.0334(5) Uani 1 1 d . . . C9 C 0.44656(19) 0.5191(3) 0.34424(9) 0.0376(5) Uani 1 1 d . . . H9 H 0.4407 0.5794 0.3163 0.045 Uiso 1 1 calc R . . C10 C 0.35944(18) 0.4349(3) 0.34080(9) 0.0353(5) Uani 1 1 d . . . C11 C 0.2526(2) 0.4311(3) 0.29486(10) 0.0423(6) Uani 1 1 d . . . C12 C 0.2225(3) 0.5267(4) 0.25401(12) 0.0631(9) Uani 1 1 d . . . H12 H 0.2722 0.5927 0.2523 0.076 Uiso 1 1 calc R . . C13 C 0.1175(3) 0.5229(4) 0.21572(13) 0.0739(10) Uani 1 1 d . . . H13 H 0.0947 0.5883 0.1886 0.089 Uiso 1 1 calc R . . C14 C 0.0474(3) 0.4227(4) 0.21792(13) 0.0778(11) Uani 1 1 d . . . H14 H -0.0239 0.4183 0.1926 0.093 Uiso 1 1 calc R . . C15 C 0.0848(3) 0.3287(4) 0.25831(13) 0.0679(9) Uani 1 1 d . . . H15 H 0.0379 0.2583 0.2591 0.081 Uiso 1 1 calc R . . C16 C 0.63965(19) 0.5953(2) 0.39198(9) 0.0351(5) Uani 1 1 d . . . C17 C 0.7120(2) 0.6473(3) 0.44033(10) 0.0437(6) Uani 1 1 d . . . H17 H 0.7002 0.6309 0.4725 0.052 Uiso 1 1 calc R . . C18 C 0.8013(2) 0.7231(3) 0.44097(12) 0.0549(7) Uani 1 1 d . . . H18 H 0.8491 0.7576 0.4737 0.066 Uiso 1 1 calc R . . C19 C 0.8207(3) 0.7484(3) 0.39424(14) 0.0608(8) Uani 1 1 d . . . H19 H 0.8810 0.8005 0.3951 0.073 Uiso 1 1 calc R . . C20 C 0.7502(3) 0.6961(3) 0.34586(13) 0.0584(8) Uani 1 1 d . . . H20 H 0.7633 0.7117 0.3139 0.070 Uiso 1 1 calc R . . C21 C 0.6608(2) 0.6209(3) 0.34483(10) 0.0456(6) Uani 1 1 d . . . H21 H 0.6134 0.5865 0.3120 0.055 Uiso 1 1 calc R . . C31 C 0.0892(2) 0.2584(3) 0.40285(10) 0.0454(6) Uani 1 1 d . . . C32 C -0.00062(19) 0.2463(3) 0.42497(9) 0.0390(5) Uani 1 1 d . . . C33 C -0.0387(2) 0.3593(3) 0.44388(11) 0.0474(6) Uani 1 1 d . . . H33 H -0.0122 0.4446 0.4398 0.057 Uiso 1 1 calc R . . C34 C -0.1152(2) 0.3475(3) 0.46872(12) 0.0502(7) Uani 1 1 d . . . H34 H -0.1400 0.4244 0.4812 0.060 Uiso 1 1 calc R . . C35 C -0.1549(2) 0.2218(3) 0.47494(11) 0.0464(6) Uani 1 1 d . . . C36 C -0.1198(2) 0.1086(3) 0.45490(12) 0.0522(7) Uani 1 1 d . . . H36 H -0.1483 0.0238 0.4578 0.063 Uiso 1 1 calc R . . C37 C -0.0426(2) 0.1212(3) 0.43063(10) 0.0446(6) Uani 1 1 d . . . H37 H -0.0185 0.0443 0.4178 0.054 Uiso 1 1 calc R . . C41 C 0.3492(2) 0.0249(3) 0.31678(10) 0.0417(6) Uani 1 1 d . . . C42 C 0.3562(2) -0.0721(3) 0.27429(9) 0.0399(5) Uani 1 1 d . . . C43 C 0.4574(2) -0.1191(3) 0.27524(10) 0.0434(6) Uani 1 1 d . . . H43 H 0.5212 -0.0932 0.3034 0.052 Uiso 1 1 calc R . . C44 C 0.4650(2) -0.2032(3) 0.23511(10) 0.0436(6) Uani 1 1 d . . . H44 H 0.5334 -0.2349 0.2367 0.052 Uiso 1 1 calc R . . C45 C 0.3707(2) -0.2408(3) 0.19234(10) 0.0436(6) Uani 1 1 d . . . C46 C 0.2695(2) -0.1926(3) 0.19080(11) 0.0484(6) Uani 1 1 d . . . H46 H 0.2060 -0.2155 0.1619 0.058 Uiso 1 1 calc R . . C47 C 0.2625(2) -0.1113(3) 0.23177(10) 0.0445(6) Uani 1 1 d . . . H47 H 0.1939 -0.0822 0.2309 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 Zn1 0.03847(16) 0.03937(19) 0.04136(16) 0.00004(12) 0.01529(12) -0.00568(12) O1 0.0557(11) 0.0547(13) 0.0574(11) -0.0089(10) 0.0280(9) -0.0007(10) O2 0.0615(12) 0.0566(13) 0.0521(11) -0.0108(10) 0.0264(9) -0.0077(10) O3 0.0610(12) 0.0694(15) 0.0531(11) -0.0209(10) 0.0152(10) 0.0042(11) O4 0.0423(10) 0.0600(13) 0.0503(10) -0.0101(9) 0.0198(8) -0.0096(9) O5 0.0674(14) 0.0666(16) 0.1029(18) -0.0180(14) 0.0471(13) -0.0282(12) O6 0.0767(15) 0.0531(14) 0.0967(17) -0.0114(12) 0.0599(14) -0.0143(11) O20 0.0996(19) 0.0582(17) 0.0975(19) -0.0236(14) 0.0419(16) -0.0178(15) N1 0.0406(10) 0.0340(12) 0.0395(10) 0.0045(8) 0.0199(8) 0.0018(9) N2 0.0322(9) 0.0336(11) 0.0324(9) 0.0033(8) 0.0116(7) 0.0003(8) N3 0.0438(12) 0.0522(15) 0.0449(12) 0.0069(10) 0.0071(9) -0.0069(10) C1 0.0520(14) 0.0369(15) 0.0505(14) 0.0044(11) 0.0282(12) -0.0005(12) C2 0.0620(16) 0.0420(16) 0.0471(14) 0.0153(12) 0.0298(13) 0.0089(13) C02 0.260(9) 0.107(5) 0.109(5) 0.004(4) 0.054(5) 0.027(5) C3 0.0565(16) 0.0525(18) 0.0363(12) 0.0110(12) 0.0153(11) 0.0119(14) C4 0.0433(13) 0.0417(15) 0.0382(12) 0.0054(11) 0.0155(10) 0.0044(11) C5 0.0388(12) 0.0312(13) 0.0354(11) 0.0046(10) 0.0168(9) 0.0063(10) C6 0.0357(11) 0.0303(13) 0.0336(11) 0.0032(9) 0.0146(9) 0.0026(9) C7 0.0362(11) 0.0349(14) 0.0341(11) 0.0024(10) 0.0092(9) 0.0013(10) C8 0.0379(11) 0.0292(13) 0.0355(11) -0.0010(9) 0.0159(9) 0.0005(9) C9 0.0426(12) 0.0344(14) 0.0350(11) 0.0074(10) 0.0127(10) -0.0007(10) C10 0.0361(11) 0.0342(14) 0.0344(11) 0.0045(10) 0.0109(9) 0.0020(10) C11 0.0411(13) 0.0463(16) 0.0362(12) 0.0067(11) 0.0099(10) -0.0002(11) C12 0.0555(17) 0.068(2) 0.0506(16) 0.0233(15) 0.0006(13) -0.0089(16) C13 0.0639(19) 0.082(3) 0.0534(17) 0.0244(17) -0.0056(15) -0.0014(19) C14 0.0560(18) 0.094(3) 0.0580(19) 0.0163(19) -0.0103(15) -0.0089(19) C15 0.0503(16) 0.076(2) 0.0603(18) 0.0099(17) -0.0014(14) -0.0187(16) C16 0.0385(12) 0.0250(12) 0.0407(12) -0.0001(9) 0.0129(10) 0.0014(9) C17 0.0447(13) 0.0399(15) 0.0429(13) -0.0022(11) 0.0115(11) -0.0011(11) C18 0.0479(15) 0.0474(18) 0.0578(17) -0.0074(13) 0.0049(13) -0.0102(13) C19 0.0523(16) 0.0513(19) 0.078(2) -0.0057(16) 0.0226(15) -0.0202(15) C20 0.0634(18) 0.059(2) 0.0618(17) -0.0002(15) 0.0329(15) -0.0160(15) C21 0.0508(14) 0.0434(16) 0.0434(13) -0.0042(11) 0.0178(11) -0.0112(12) C31 0.0361(12) 0.0549(18) 0.0421(13) -0.0056(12) 0.0103(10) -0.0108(12) C32 0.0334(11) 0.0430(15) 0.0357(11) -0.0032(11) 0.0065(9) -0.0074(11) C33 0.0486(14) 0.0333(15) 0.0607(16) -0.0011(12) 0.0200(12) -0.0082(12) C34 0.0503(15) 0.0352(15) 0.0693(18) -0.0068(13) 0.0264(14) -0.0006(12) C35 0.0448(14) 0.0430(17) 0.0553(15) -0.0025(12) 0.0228(12) -0.0035(12) C36 0.0610(17) 0.0348(16) 0.0704(18) -0.0063(13) 0.0350(15) -0.0101(13) C37 0.0476(14) 0.0374(16) 0.0505(14) -0.0079(11) 0.0196(11) -0.0033(12) C41 0.0537(15) 0.0387(15) 0.0364(12) 0.0080(11) 0.0205(11) 0.0024(12) C42 0.0486(13) 0.0371(15) 0.0361(12) 0.0076(10) 0.0177(10) 0.0029(11) C43 0.0429(13) 0.0482(17) 0.0366(12) 0.0039(11) 0.0113(10) 0.0033(12) C44 0.0412(13) 0.0476(16) 0.0424(13) 0.0019(11) 0.0157(10) 0.0059(11) C45 0.0531(14) 0.0398(15) 0.0380(12) 0.0027(11) 0.0164(11) 0.0002(12) C46 0.0464(14) 0.0463(17) 0.0469(14) 0.0006(12) 0.0098(11) -0.0026(12) C47 0.0416(13) 0.0460(17) 0.0472(14) 0.0060(12) 0.0174(11) 0.0047(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 O1 1.983(2) . ? Zn1 O4 1.9855(18) . ? Zn1 N2 2.080(2) . ? Zn1 N1 2.164(2) . ? Zn1 N3 2.202(2) . ? O1 C41 1.267(3) . ? O2 C41 1.237(3) . ? O3 C45 1.343(3) . ? O3 H3A 0.8200 . ? O4 C31 1.262(3) . ? O5 C31 1.235(4) . ? O6 C35 1.355(3) . ? O6 H6A 0.8200 . ? O20 C02 1.431(6) . ? O20 H20D 0.8500 . ? N1 C1 1.330(3) . ? N1 C5 1.348(3) . ? N2 C6 1.324(3) . ? N2 C10 1.331(3) . ? N3 C15 1.327(4) . ? N3 C11 1.332(3) . ? C1 C2 1.372(4) . ? C1 H1 0.9300 . ? C2 C3 1.363(4) . ? C2 H2 0.9300 . ? C02 H02A 0.9600 . ? C02 H02B 0.9600 . ? C02 H02C 0.9600 . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 C6 1.486(3) . ? C6 C7 1.385(3) . ? C7 C8 1.396(3) . ? C7 H7 0.9300 . ? C8 C9 1.386(3) . ? C8 C16 1.476(3) . ? C9 C10 1.381(3) . ? C9 H9 0.9300 . ? C10 C11 1.483(3) . ? C11 C12 1.379(4) . ? C12 C13 1.379(4) . ? C12 H12 0.9300 . ? C13 C14 1.359(5) . ? C13 H13 0.9300 . ? C14 C15 1.364(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.385(3) . ? C16 C21 1.390(3) . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 C19 1.368(5) . ? C18 H18 0.9300 . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 C21 1.372(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C31 C32 1.485(4) . ? C32 C37 1.378(4) . ? C32 C33 1.383(4) . ? C33 C34 1.379(4) . ? C33 H33 0.9300 . ? C34 C35 1.375(4) . ? C34 H34 0.9300 . ? C35 C36 1.381(4) . ? C36 C37 1.375(4) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C41 C42 1.501(4) . ? C42 C47 1.384(4) . ? C42 C43 1.387(4) . ? C43 C44 1.376(4) . ? C43 H43 0.9300 . ? C44 C45 1.387(4) . ? C44 H44 0.9300 . ? C45 C46 1.387(4) . ? C46 C47 1.375(4) . ? C46 H46 0.9300 . ? C47 H47 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 O1 Zn1 O4 100.73(8) . . ? O1 Zn1 N2 119.44(8) . . ? O4 Zn1 N2 139.56(8) . . ? O1 Zn1 N1 108.85(8) . . ? O4 Zn1 N1 96.76(8) . . ? N2 Zn1 N1 75.59(8) . . ? O1 Zn1 N3 93.71(9) . . ? O4 Zn1 N3 99.64(9) . . ? N2 Zn1 N3 74.85(8) . . ? N1 Zn1 N3 149.01(8) . . ? C41 O1 Zn1 113.26(18) . . ? C45 O3 H3A 109.5 . . ? C31 O4 Zn1 107.15(17) . . ? C35 O6 H6A 109.5 . . ? C02 O20 H20D 101.9 . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Zn1 126.11(18) . . ? C5 N1 Zn1 115.26(15) . . ? C6 N2 C10 120.8(2) . . ? C6 N2 Zn1 118.80(16) . . ? C10 N2 Zn1 119.25(15) . . ? C15 N3 C11 118.2(2) . . ? C15 N3 Zn1 127.0(2) . . ? C11 N3 Zn1 114.69(16) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 118.7(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? O20 C02 H02A 109.5 . . ? O20 C02 H02B 109.5 . . ? H02A C02 H02B 109.5 . . ? O20 C02 H02C 109.5 . . ? H02A C02 H02C 109.5 . . ? H02B C02 H02C 109.5 . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.6(2) . . ? N1 C5 C6 114.7(2) . . ? C4 C5 C6 123.7(2) . . ? N2 C6 C7 121.1(2) . . ? N2 C6 C5 114.3(2) . . ? C7 C6 C5 124.6(2) . . ? C6 C7 C8 119.6(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 117.4(2) . . ? C9 C8 C16 120.8(2) . . ? C7 C8 C16 121.7(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N2 C10 C9 120.9(2) . . ? N2 C10 C11 113.9(2) . . ? C9 C10 C11 125.2(2) . . ? N3 C11 C12 121.4(2) . . ? N3 C11 C10 115.6(2) . . ? C12 C11 C10 122.9(2) . . ? C11 C12 C13 118.9(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 119.5(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 118.0(3) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? N3 C15 C14 123.8(3) . . ? N3 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? C17 C16 C21 118.1(2) . . ? C17 C16 C8 122.2(2) . . ? C21 C16 C8 119.7(2) . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 121.0(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 119.4(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? C21 C20 C19 120.0(3) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 121.2(3) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? O5 C31 O4 122.0(3) . . ? O5 C31 C32 120.1(3) . . ? O4 C31 C32 117.8(2) . . ? C37 C32 C33 118.4(2) . . ? C37 C32 C31 120.8(2) . . ? C33 C32 C31 120.7(2) . . ? C34 C33 C32 121.1(3) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C35 C34 C33 119.9(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? O6 C35 C34 122.3(3) . . ? O6 C35 C36 118.1(3) . . ? C34 C35 C36 119.6(2) . . ? C37 C36 C35 120.1(3) . . ? C37 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? C36 C37 C32 121.0(3) . . ? C36 C37 H37 119.5 . . ? C32 C37 H37 119.5 . . ? O2 C41 O1 123.4(2) . . ? O2 C41 C42 119.2(2) . . ? O1 C41 C42 117.4(2) . . ? C47 C42 C43 118.5(2) . . ? C47 C42 C41 120.8(2) . . ? C43 C42 C41 120.6(2) . . ? C44 C43 C42 121.0(2) . . ? C44 C43 H43 119.5 . . ? C42 C43 H43 119.5 . . ? C43 C44 C45 120.1(2) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? O3 C45 C46 118.1(2) . . ? O3 C45 C44 122.8(2) . . ? C46 C45 C44 119.1(2) . . ? C47 C46 C45 120.4(3) . . ? C47 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? C46 C47 C42 120.9(2) . . ? C46 C47 H47 119.5 . . ? C42 C47 H47 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O1 C41 -167.60(18) . . . . ? N2 Zn1 O1 C41 17.2(2) . . . . ? N1 Zn1 O1 C41 -66.57(19) . . . . ? N3 Zn1 O1 C41 91.85(19) . . . . ? O1 Zn1 O4 C31 -172.55(18) . . . . ? N2 Zn1 O4 C31 1.0(2) . . . . ? N1 Zn1 O4 C31 76.74(18) . . . . ? N3 Zn1 O4 C31 -76.87(19) . . . . ? O1 Zn1 N1 C1 -71.1(2) . . . . ? O4 Zn1 N1 C1 32.7(2) . . . . ? N2 Zn1 N1 C1 172.2(2) . . . . ? N3 Zn1 N1 C1 154.4(2) . . . . ? O1 Zn1 N1 C5 113.29(17) . . . . ? O4 Zn1 N1 C5 -142.90(17) . . . . ? N2 Zn1 N1 C5 -3.36(16) . . . . ? N3 Zn1 N1 C5 -21.2(3) . . . . ? O1 Zn1 N2 C6 -94.03(18) . . . . ? O4 Zn1 N2 C6 93.2(2) . . . . ? N1 Zn1 N2 C6 9.75(16) . . . . ? N3 Zn1 N2 C6 -179.68(19) . . . . ? O1 Zn1 N2 C10 73.79(19) . . . . ? O4 Zn1 N2 C10 -98.98(19) . . . . ? N1 Zn1 N2 C10 177.57(19) . . . . ? N3 Zn1 N2 C10 -11.86(17) . . . . ? O1 Zn1 N3 C15 70.3(3) . . . . ? O4 Zn1 N3 C15 -31.2(3) . . . . ? N2 Zn1 N3 C15 -170.1(3) . . . . ? N1 Zn1 N3 C15 -152.2(3) . . . . ? O1 Zn1 N3 C11 -113.1(2) . . . . ? O4 Zn1 N3 C11 145.3(2) . . . . ? N2 Zn1 N3 C11 6.39(19) . . . . ? N1 Zn1 N3 C11 24.3(3) . . . . ? C5 N1 C1 C2 -0.4(4) . . . . ? Zn1 N1 C1 C2 -175.88(19) . . . . ? N1 C1 C2 C3 0.4(4) . . . . ? C1 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C1 N1 C5 C4 -0.1(3) . . . . ? Zn1 N1 C5 C4 175.85(18) . . . . ? C1 N1 C5 C6 -178.4(2) . . . . ? Zn1 N1 C5 C6 -2.5(3) . . . . ? C3 C4 C5 N1 0.6(4) . . . . ? C3 C4 C5 C6 178.7(2) . . . . ? C10 N2 C6 C7 -2.0(3) . . . . ? Zn1 N2 C6 C7 165.60(18) . . . . ? C10 N2 C6 C5 178.4(2) . . . . ? Zn1 N2 C6 C5 -14.0(3) . . . . ? N1 C5 C6 N2 10.5(3) . . . . ? C4 C5 C6 N2 -167.8(2) . . . . ? N1 C5 C6 C7 -169.1(2) . . . . ? C4 C5 C6 C7 12.6(4) . . . . ? N2 C6 C7 C8 0.0(4) . . . . ? C5 C6 C7 C8 179.5(2) . . . . ? C6 C7 C8 C9 2.5(3) . . . . ? C6 C7 C8 C16 -176.0(2) . . . . ? C7 C8 C9 C10 -3.1(4) . . . . ? C16 C8 C9 C10 175.4(2) . . . . ? C6 N2 C10 C9 1.4(4) . . . . ? Zn1 N2 C10 C9 -166.14(18) . . . . ? C6 N2 C10 C11 -177.4(2) . . . . ? Zn1 N2 C10 C11 15.0(3) . . . . ? C8 C9 C10 N2 1.2(4) . . . . ? C8 C9 C10 C11 179.9(2) . . . . ? C15 N3 C11 C12 -1.4(5) . . . . ? Zn1 N3 C11 C12 -178.2(2) . . . . ? C15 N3 C11 C10 175.9(3) . . . . ? Zn1 N3 C11 C10 -1.0(3) . . . . ? N2 C10 C11 N3 -8.7(3) . . . . ? C9 C10 C11 N3 172.5(3) . . . . ? N2 C10 C11 C12 168.6(3) . . . . ? C9 C10 C11 C12 -10.3(4) . . . . ? N3 C11 C12 C13 3.2(5) . . . . ? C10 C11 C12 C13 -173.8(3) . . . . ? C11 C12 C13 C14 -2.3(6) . . . . ? C12 C13 C14 C15 -0.3(6) . . . . ? C11 N3 C15 C14 -1.4(6) . . . . ? Zn1 N3 C15 C14 175.0(3) . . . . ? C13 C14 C15 N3 2.2(6) . . . . ? C9 C8 C16 C17 147.3(3) . . . . ? C7 C8 C16 C17 -34.2(4) . . . . ? C9 C8 C16 C21 -33.2(3) . . . . ? C7 C8 C16 C21 145.2(2) . . . . ? C21 C16 C17 C18 0.6(4) . . . . ? C8 C16 C17 C18 -179.9(2) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 -0.6(5) . . . . ? C18 C19 C20 C21 0.9(5) . . . . ? C19 C20 C21 C16 -0.4(5) . . . . ? C17 C16 C21 C20 -0.3(4) . . . . ? C8 C16 C21 C20 -179.8(3) . . . . ? Zn1 O4 C31 O5 6.9(3) . . . . ? Zn1 O4 C31 C32 -170.30(18) . . . . ? O5 C31 C32 C37 -163.6(3) . . . . ? O4 C31 C32 C37 13.7(4) . . . . ? O5 C31 C32 C33 11.8(4) . . . . ? O4 C31 C32 C33 -170.9(2) . . . . ? C37 C32 C33 C34 1.2(4) . . . . ? C31 C32 C33 C34 -174.4(2) . . . . ? C32 C33 C34 C35 0.0(4) . . . . ? C33 C34 C35 O6 178.9(3) . . . . ? C33 C34 C35 C36 -1.7(4) . . . . ? O6 C35 C36 C37 -178.3(3) . . . . ? C34 C35 C36 C37 2.3(4) . . . . ? C35 C36 C37 C32 -1.2(4) . . . . ? C33 C32 C37 C36 -0.6(4) . . . . ? C31 C32 C37 C36 175.0(2) . . . . ? Zn1 O1 C41 O2 12.5(3) . . . . ? Zn1 O1 C41 C42 -166.95(17) . . . . ? O2 C41 C42 C47 -158.6(3) . . . . ? O1 C41 C42 C47 20.8(4) . . . . ? O2 C41 C42 C43 18.0(4) . . . . ? O1 C41 C42 C43 -162.5(2) . . . . ? C47 C42 C43 C44 -0.3(4) . . . . ? C41 C42 C43 C44 -177.1(2) . . . . ? C42 C43 C44 C45 1.0(4) . . . . ? C43 C44 C45 O3 179.7(3) . . . . ? C43 C44 C45 C46 -0.1(4) . . . . ? O3 C45 C46 C47 178.7(3) . . . . ? C44 C45 C46 C47 -1.5(4) . . . . ? C45 C46 C47 C42 2.2(4) . . . . ? C43 C42 C47 C46 -1.3(4) . . . . ? C41 C42 C47 C46 175.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.752 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.065 data_m2 _database_code_depnum_ccdc_archive 'CCDC 916059' #TrackingRef '5-M.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 N3 O6 Zn' _chemical_formula_sum 'C35 H25 N3 O6 Zn' _chemical_formula_weight 648.97 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.998(2) _cell_length_b 14.822(2) _cell_length_c 15.489(2) _cell_angle_alpha 106.615(7) _cell_angle_beta 103.451(7) _cell_angle_gamma 91.595(7) _cell_volume 2979.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 52512 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 28.47 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52512 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.47 _reflns_number_total 14722 _reflns_number_gt 10316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0545P)^2^+2.2868P] 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 14722 _refine_ls_number_parameters 811 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.48499(2) 0.22423(2) 0.75224(2) 0.04657(9) Uani 1 1 d . . . Zn2 Zn 0.96606(2) 0.31738(2) 0.15193(2) 0.04691(9) Uani 1 1 d . . . O1 O 0.34770(16) 0.23991(17) 0.76492(17) 0.0683(6) Uani 1 1 d . . . O2 O 0.52036(15) 0.26998(16) 0.65409(14) 0.0595(5) Uani 1 1 d . . . O3 O 0.66535(17) 0.22896(17) 0.71129(16) 0.0704(6) Uani 1 1 d . . . O4 O 0.29475(19) 0.1666(3) 0.61492(19) 0.0981(9) Uani 1 1 d . . . O5 O 0.5043(2) 0.3663(2) 0.5400(2) 0.1044(10) Uani 1 1 d . . . H5A H 0.4864 0.3386 0.5733 0.157 Uiso 1 1 calc R . . O6 O 0.1110(3) 0.1302(4) 0.5424(2) 0.170(2) Uani 1 1 d . . . H6A H 0.1703 0.1325 0.5452 0.254 Uiso 1 1 calc R . . O7 O 1.10919(14) 0.34932(15) 0.17448(16) 0.0618(5) Uani 1 1 d . . . O8 O 1.12390(18) 0.2323(2) 0.05463(18) 0.0863(8) Uani 1 1 d . . . O9 O 1.2929(2) 0.1881(2) 0.0392(2) 0.1066(10) Uani 1 1 d . . . H9A H 1.2325 0.1860 0.0256 0.160 Uiso 1 1 calc R . . O10 O 0.94172(16) 0.40622(16) 0.26257(14) 0.0653(6) Uani 1 1 d . . . O11 O 0.78012(18) 0.38631(17) 0.20455(16) 0.0769(7) Uani 1 1 d . . . O12 O 0.67239(18) 0.5031(2) 0.2884(2) 0.1045(10) Uani 1 1 d . . . H12A H 0.6841 0.4585 0.2480 0.157 Uiso 1 1 calc R . . N1 N 0.54730(16) 0.35710(16) 0.86393(16) 0.0477(5) Uani 1 1 d . . . N2 N 0.55616(14) 0.18249(14) 0.86574(14) 0.0392(4) Uani 1 1 d . . . N3 N 0.48234(16) 0.07201(16) 0.69847(15) 0.0484(5) Uani 1 1 d . . . N4 N 0.90532(16) 0.39331(15) 0.05284(16) 0.0470(5) Uani 1 1 d . . . N5 N 0.89322(14) 0.21200(14) 0.03369(14) 0.0374(4) Uani 1 1 d . . . N6 N 0.97155(16) 0.18882(17) 0.19280(15) 0.0484(5) Uani 1 1 d . . . C1 C 0.5441(2) 0.4445(2) 0.8563(2) 0.0591(8) Uani 1 1 d . . . H1 H 0.5119 0.4521 0.7994 0.071 Uiso 1 1 calc R . . C2 C 0.5865(2) 0.5239(2) 0.9289(3) 0.0651(8) Uani 1 1 d . . . H2 H 0.5833 0.5837 0.9210 0.078 Uiso 1 1 calc R . . C3 C 0.6332(2) 0.5135(2) 1.0127(3) 0.0635(8) Uani 1 1 d . . . H3 H 0.6617 0.5661 1.0629 0.076 Uiso 1 1 calc R . . C4 C 0.6375(2) 0.42361(19) 1.0219(2) 0.0533(7) Uani 1 1 d . . . H4 H 0.6694 0.4148 1.0782 0.064 Uiso 1 1 calc R . . C5 C 0.59358(18) 0.34689(17) 0.94587(18) 0.0408(5) Uani 1 1 d . . . C6 C 0.59541(17) 0.24712(17) 0.94763(17) 0.0374(5) Uani 1 1 d . . . C7 C 0.63485(18) 0.22106(18) 1.02634(18) 0.0412(5) Uani 1 1 d . . . H7 H 0.6624 0.2671 1.0827 0.049 Uiso 1 1 calc R . . C8 C 0.63320(17) 0.12569(17) 1.02108(17) 0.0389(5) Uani 1 1 d . . . C9 C 0.59482(18) 0.06009(18) 0.93368(18) 0.0424(5) Uani 1 1 d . . . H9 H 0.5948 -0.0043 0.9268 0.051 Uiso 1 1 calc R . . C10 C 0.55686(17) 0.09042(17) 0.85741(17) 0.0400(5) Uani 1 1 d . . . C11 C 0.51559(18) 0.02687(18) 0.76151(18) 0.0429(5) Uani 1 1 d . . . C12 C 0.5118(2) -0.0709(2) 0.7366(2) 0.0572(7) Uani 1 1 d . . . H12 H 0.5349 -0.1011 0.7812 0.069 Uiso 1 1 calc R . . C13 C 0.4734(3) -0.1227(2) 0.6451(2) 0.0711(9) Uani 1 1 d . . . H13 H 0.4695 -0.1884 0.6273 0.085 Uiso 1 1 calc R . . C14 C 0.4408(3) -0.0768(3) 0.5806(2) 0.0751(10) Uani 1 1 d . . . H14 H 0.4154 -0.1106 0.5182 0.090 Uiso 1 1 calc R . . C15 C 0.4465(2) 0.0202(3) 0.6096(2) 0.0646(8) Uani 1 1 d . . . H15 H 0.4243 0.0513 0.5655 0.078 Uiso 1 1 calc R . . C16 C 0.67102(17) 0.09560(18) 1.10560(18) 0.0417(5) Uani 1 1 d . . . C17 C 0.6647(2) 0.0006(2) 1.1007(2) 0.0527(7) Uani 1 1 d . . . H17 H 0.6365 -0.0446 1.0440 0.063 Uiso 1 1 calc R . . C18 C 0.6995(2) -0.0279(2) 1.1789(2) 0.0635(8) Uani 1 1 d . . . H18 H 0.6955 -0.0919 1.1742 0.076 Uiso 1 1 calc R . . C19 C 0.7394(2) 0.0371(3) 1.2623(2) 0.0691(9) Uani 1 1 d . . . H19 H 0.7621 0.0179 1.3150 0.083 Uiso 1 1 calc R . . C20 C 0.7462(3) 0.1313(3) 1.2689(2) 0.0718(9) Uani 1 1 d . . . H20 H 0.7740 0.1758 1.3262 0.086 Uiso 1 1 calc R . . C21 C 0.7122(2) 0.1608(2) 1.1914(2) 0.0610(8) Uani 1 1 d . . . H21 H 0.7171 0.2251 1.1969 0.073 Uiso 1 1 calc R . . C22 C 0.9111(2) 0.4874(2) 0.0687(2) 0.0582(7) Uani 1 1 d . . . H22 H 0.9405 0.5264 0.1285 0.070 Uiso 1 1 calc R . . C23 C 0.8758(2) 0.5282(2) 0.0007(3) 0.0643(8) Uani 1 1 d . . . H23 H 0.8805 0.5937 0.0138 0.077 Uiso 1 1 calc R . . C24 C 0.8331(2) 0.4704(2) -0.0874(2) 0.0614(8) Uani 1 1 d . . . H24 H 0.8101 0.4963 -0.1355 0.074 Uiso 1 1 calc R . . C25 C 0.8244(2) 0.37391(19) -0.1045(2) 0.0509(6) Uani 1 1 d . . . H25 H 0.7940 0.3340 -0.1637 0.061 Uiso 1 1 calc R . . C26 C 0.86110(18) 0.33744(17) -0.03289(18) 0.0418(5) Uani 1 1 d . . . C27 C 0.85540(17) 0.23422(16) -0.04395(17) 0.0374(5) Uani 1 1 d . . . C28 C 0.81426(18) 0.16499(17) -0.12712(17) 0.0388(5) Uani 1 1 d . . . H28 H 0.7849 0.1819 -0.1798 0.047 Uiso 1 1 calc R . . C29 C 0.81680(17) 0.06967(16) -0.13200(16) 0.0363(5) Uani 1 1 d . . . C30 C 0.85773(17) 0.04895(17) -0.04976(17) 0.0394(5) Uani 1 1 d . . . H30 H 0.8605 -0.0137 -0.0498 0.047 Uiso 1 1 calc R . . C31 C 0.89413(16) 0.12112(17) 0.03158(16) 0.0365(5) Uani 1 1 d . . . C32 C 0.93594(17) 0.10817(18) 0.12378(17) 0.0404(5) Uani 1 1 d . . . C33 C 0.9365(2) 0.0214(2) 0.1399(2) 0.0515(6) Uani 1 1 d . . . H33 H 0.9122 -0.0338 0.0914 0.062 Uiso 1 1 calc R . . C34 C 0.9741(2) 0.0183(3) 0.2297(2) 0.0621(8) Uani 1 1 d . . . H34 H 0.9752 -0.0394 0.2423 0.074 Uiso 1 1 calc R . . C35 C 1.0092(2) 0.0998(3) 0.2995(2) 0.0676(9) Uani 1 1 d . . . H35 H 1.0336 0.0987 0.3604 0.081 Uiso 1 1 calc R . . C36 C 1.0080(2) 0.1836(3) 0.2788(2) 0.0615(8) Uani 1 1 d . . . H36 H 1.0336 0.2392 0.3265 0.074 Uiso 1 1 calc R . . C37 C 0.77838(18) -0.00517(17) -0.22206(17) 0.0393(5) Uani 1 1 d . . . C38 C 0.7608(2) -0.09925(19) -0.2276(2) 0.0550(7) Uani 1 1 d . . . H38 H 0.7729 -0.1166 -0.1732 0.066 Uiso 1 1 calc R . . C39 C 0.7256(3) -0.1682(2) -0.3126(2) 0.0688(9) Uani 1 1 d . . . H39 H 0.7138 -0.2309 -0.3146 0.083 Uiso 1 1 calc R . . C40 C 0.7081(2) -0.1447(2) -0.3930(2) 0.0639(8) Uani 1 1 d . . . H40 H 0.6840 -0.1909 -0.4500 0.077 Uiso 1 1 calc R . . C41 C 0.7263(3) -0.0522(2) -0.3892(2) 0.0673(9) Uani 1 1 d . . . H41 H 0.7156 -0.0359 -0.4442 0.081 Uiso 1 1 calc R . . C42 C 0.7602(2) 0.0168(2) -0.30530(19) 0.0576(7) Uani 1 1 d . . . H42 H 0.7711 0.0794 -0.3042 0.069 Uiso 1 1 calc R . . C51 C 0.2804(2) 0.2055(3) 0.6946(3) 0.0663(9) Uani 1 1 d . . . C52 C 0.1759(2) 0.2066(2) 0.7028(2) 0.0588(7) Uani 1 1 d . . . C53 C 0.1550(3) 0.2434(3) 0.7896(3) 0.0782(10) Uani 1 1 d . . . H53 H 0.2068 0.2678 0.8423 0.094 Uiso 1 1 calc R . . C54 C 0.0606(3) 0.2442(3) 0.7984(4) 0.0959(14) Uani 1 1 d . . . H54 H 0.0478 0.2678 0.8566 0.115 Uiso 1 1 calc R . . C55 C -0.0152(3) 0.2099(3) 0.7206(4) 0.0961(14) Uani 1 1 d . . . H55 H -0.0796 0.2136 0.7268 0.115 Uiso 1 1 calc R . . C56 C -0.0008(3) 0.1710(4) 0.6359(4) 0.1125(18) Uani 1 1 d . . . H56 H -0.0539 0.1461 0.5845 0.135 Uiso 1 1 calc R . . C57 C 0.0976(3) 0.1689(4) 0.6268(3) 0.1003(15) Uani 1 1 d . . . C61 C 0.6135(2) 0.2663(2) 0.65942(19) 0.0502(6) Uani 1 1 d . . . C62 C 0.6552(2) 0.3108(2) 0.6007(2) 0.0546(7) Uani 1 1 d . . . C63 C 0.6004(3) 0.3596(3) 0.5460(2) 0.0670(9) Uani 1 1 d . . . C64 C 0.6459(4) 0.4042(4) 0.4963(3) 0.1145(18) Uani 1 1 d . . . H64 H 0.6106 0.4405 0.4625 0.137 Uiso 1 1 calc R . . C65 C 0.7421(5) 0.3945(6) 0.4977(5) 0.155(3) Uani 1 1 d . . . H65 H 0.7720 0.4236 0.4636 0.186 Uiso 1 1 calc R . . C66 C 0.7959(4) 0.3430(6) 0.5478(5) 0.157(3) Uani 1 1 d . . . H66 H 0.8613 0.3349 0.5466 0.188 Uiso 1 1 calc R . . C67 C 0.7518(3) 0.3037(4) 0.5999(4) 0.1063(16) Uani 1 1 d . . . H67 H 0.7891 0.2707 0.6363 0.128 Uiso 1 1 calc R . . C71 C 1.1597(2) 0.2972(2) 0.1277(2) 0.0522(7) Uani 1 1 d . . . C72 C 1.2691(2) 0.31381(19) 0.1644(2) 0.0520(7) Uani 1 1 d . . . C73 C 1.3299(3) 0.2566(2) 0.1190(3) 0.0698(9) Uani 1 1 d . . . C74 C 1.4313(3) 0.2678(3) 0.1563(4) 0.0948(15) Uani 1 1 d . . . H74 H 1.4716 0.2284 0.1261 0.114 Uiso 1 1 calc R . . C75 C 1.4708(3) 0.3363(4) 0.2365(5) 0.1112(19) Uani 1 1 d . . . H75 H 1.5388 0.3441 0.2607 0.133 Uiso 1 1 calc R . . C76 C 1.4131(3) 0.3953(3) 0.2839(3) 0.0951(14) Uani 1 1 d . . . H76 H 1.4420 0.4419 0.3395 0.114 Uiso 1 1 calc R . . C77 C 1.3121(2) 0.3845(2) 0.2479(3) 0.0686(9) Uani 1 1 d . . . H77 H 1.2726 0.4242 0.2792 0.082 Uiso 1 1 calc R . . C81 C 0.8553(2) 0.42822(19) 0.26514(18) 0.0487(6) Uani 1 1 d . . . C82 C 0.8457(2) 0.5088(2) 0.3435(2) 0.0512(6) Uani 1 1 d . . . C83 C 0.9279(3) 0.5523(4) 0.4120(3) 0.121(2) Uani 1 1 d . . . H83 H 0.9892 0.5310 0.4087 0.145 Uiso 1 1 calc R . . C84 C 0.9207(4) 0.6273(5) 0.4859(4) 0.209(5) Uani 1 1 d . . . H84 H 0.9769 0.6561 0.5327 0.251 Uiso 1 1 calc R . . C85 C 0.8319(4) 0.6590(5) 0.4905(4) 0.181(4) Uani 1 1 d . . . H85 H 0.8284 0.7110 0.5400 0.218 Uiso 1 1 calc R . . C86 C 0.7490(3) 0.6180(3) 0.4262(3) 0.1003(15) Uani 1 1 d . . . H86 H 0.6883 0.6396 0.4318 0.120 Uiso 1 1 calc R . . C87 C 0.7552(2) 0.5422(2) 0.3507(2) 0.0619(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.04163(17) 0.05493(19) 0.04490(18) 0.02247(14) 0.00501(13) 0.00431(13) Zn2 0.04139(17) 0.04783(18) 0.04186(17) 0.00145(13) 0.00674(13) 0.00579(13) O1 0.0519(12) 0.0726(14) 0.0810(16) 0.0329(12) 0.0060(11) 0.0018(10) O2 0.0511(12) 0.0745(14) 0.0595(12) 0.0329(11) 0.0112(9) 0.0019(10) O3 0.0748(15) 0.0780(15) 0.0682(14) 0.0437(13) 0.0085(11) 0.0175(12) O4 0.0711(16) 0.165(3) 0.0673(17) 0.0439(18) 0.0217(13) 0.0238(17) O5 0.0732(18) 0.149(3) 0.117(2) 0.093(2) 0.0056(16) 0.0234(17) O6 0.091(2) 0.329(7) 0.072(2) 0.052(3) 0.0014(18) 0.000(3) O7 0.0423(11) 0.0574(12) 0.0783(15) 0.0112(11) 0.0120(10) 0.0054(9) O8 0.0681(15) 0.0985(19) 0.0673(16) -0.0087(14) 0.0134(12) -0.0113(13) O9 0.114(2) 0.0852(19) 0.125(3) 0.0066(19) 0.070(2) 0.0131(17) O10 0.0662(14) 0.0698(14) 0.0459(11) -0.0024(10) 0.0096(10) 0.0237(11) O11 0.0730(15) 0.0748(15) 0.0568(14) -0.0028(11) -0.0038(11) -0.0085(12) O12 0.0573(15) 0.122(2) 0.095(2) -0.0069(18) -0.0061(14) 0.0103(15) N1 0.0436(12) 0.0498(12) 0.0546(13) 0.0246(11) 0.0107(10) 0.0064(9) N2 0.0372(10) 0.0400(11) 0.0409(11) 0.0146(9) 0.0079(9) 0.0026(8) N3 0.0454(12) 0.0551(13) 0.0400(12) 0.0116(10) 0.0055(9) 0.0022(10) N4 0.0460(12) 0.0391(11) 0.0523(13) 0.0082(10) 0.0126(10) 0.0048(9) N5 0.0318(10) 0.0419(11) 0.0373(11) 0.0106(8) 0.0077(8) 0.0077(8) N6 0.0449(12) 0.0573(13) 0.0366(12) 0.0088(10) 0.0044(9) 0.0077(10) C1 0.0583(17) 0.0566(17) 0.075(2) 0.0373(16) 0.0185(15) 0.0103(14) C2 0.067(2) 0.0444(16) 0.095(3) 0.0322(17) 0.0267(18) 0.0088(14) C3 0.0633(19) 0.0396(15) 0.083(2) 0.0089(15) 0.0215(17) -0.0005(13) C4 0.0560(16) 0.0446(14) 0.0558(17) 0.0116(12) 0.0116(13) 0.0025(12) C5 0.0377(12) 0.0398(12) 0.0468(14) 0.0134(11) 0.0136(11) 0.0048(10) C6 0.0328(11) 0.0406(12) 0.0400(13) 0.0132(10) 0.0098(10) 0.0040(9) C7 0.0385(13) 0.0450(13) 0.0392(13) 0.0119(11) 0.0093(10) 0.0020(10) C8 0.0309(11) 0.0472(13) 0.0403(13) 0.0158(11) 0.0092(10) 0.0036(10) C9 0.0420(13) 0.0385(12) 0.0467(14) 0.0142(11) 0.0093(11) 0.0023(10) C10 0.0350(12) 0.0395(12) 0.0441(14) 0.0128(10) 0.0075(10) 0.0009(9) C11 0.0378(13) 0.0433(13) 0.0438(14) 0.0094(11) 0.0080(11) -0.0011(10) C12 0.0638(18) 0.0442(15) 0.0579(18) 0.0085(13) 0.0134(14) 0.0039(13) C13 0.086(2) 0.0517(18) 0.061(2) -0.0042(15) 0.0181(18) -0.0004(16) C14 0.079(2) 0.076(2) 0.0491(19) -0.0057(17) 0.0062(17) -0.0010(18) C15 0.0633(19) 0.079(2) 0.0406(16) 0.0078(15) 0.0039(14) 0.0041(16) C16 0.0343(12) 0.0517(14) 0.0453(14) 0.0222(12) 0.0119(10) 0.0085(10) C17 0.0535(16) 0.0568(16) 0.0561(17) 0.0277(14) 0.0152(13) 0.0127(13) C18 0.067(2) 0.070(2) 0.071(2) 0.0441(18) 0.0217(17) 0.0193(16) C19 0.063(2) 0.099(3) 0.065(2) 0.052(2) 0.0170(16) 0.0206(18) C20 0.071(2) 0.091(3) 0.0491(18) 0.0263(17) 0.0004(15) 0.0046(18) C21 0.0644(19) 0.0659(19) 0.0488(17) 0.0209(14) 0.0030(14) 0.0020(15) C22 0.0577(17) 0.0403(14) 0.0672(19) 0.0024(13) 0.0148(15) 0.0025(12) C23 0.068(2) 0.0390(14) 0.085(2) 0.0175(15) 0.0197(17) 0.0061(13) C24 0.0656(19) 0.0509(16) 0.074(2) 0.0279(16) 0.0164(16) 0.0105(14) C25 0.0566(16) 0.0437(14) 0.0543(16) 0.0179(12) 0.0136(13) 0.0059(12) C26 0.0375(13) 0.0399(13) 0.0481(15) 0.0106(11) 0.0142(11) 0.0066(10) C27 0.0336(12) 0.0387(12) 0.0420(13) 0.0129(10) 0.0121(10) 0.0078(9) C28 0.0413(13) 0.0410(12) 0.0357(12) 0.0137(10) 0.0093(10) 0.0077(10) C29 0.0335(11) 0.0379(12) 0.0367(12) 0.0102(10) 0.0086(9) 0.0046(9) C30 0.0400(13) 0.0365(12) 0.0418(13) 0.0131(10) 0.0086(10) 0.0067(10) C31 0.0297(11) 0.0419(12) 0.0393(12) 0.0140(10) 0.0088(9) 0.0077(9) C32 0.0325(12) 0.0518(14) 0.0377(13) 0.0141(11) 0.0087(10) 0.0094(10) C33 0.0478(15) 0.0592(16) 0.0491(16) 0.0226(13) 0.0065(12) 0.0103(12) C34 0.0604(18) 0.075(2) 0.0595(19) 0.0367(17) 0.0099(15) 0.0158(15) C35 0.0571(18) 0.099(3) 0.0482(18) 0.0329(18) 0.0027(14) 0.0170(17) C36 0.0554(17) 0.080(2) 0.0408(16) 0.0132(15) 0.0011(13) 0.0117(15) C37 0.0392(13) 0.0389(12) 0.0360(12) 0.0079(10) 0.0057(10) 0.0066(10) C38 0.077(2) 0.0430(14) 0.0425(15) 0.0094(12) 0.0153(14) 0.0016(13) C39 0.096(3) 0.0424(15) 0.059(2) 0.0029(14) 0.0183(18) 0.0007(15) C40 0.070(2) 0.0572(18) 0.0455(17) -0.0027(13) 0.0002(14) 0.0075(15) C41 0.086(2) 0.0644(19) 0.0386(16) 0.0099(14) -0.0038(15) 0.0117(17) C42 0.073(2) 0.0472(15) 0.0428(15) 0.0126(12) -0.0025(14) 0.0067(13) C51 0.0578(19) 0.084(2) 0.068(2) 0.0455(19) 0.0078(17) 0.0084(16) C52 0.0443(15) 0.0689(19) 0.071(2) 0.0352(16) 0.0108(14) 0.0101(13) C53 0.072(2) 0.065(2) 0.094(3) 0.0098(19) 0.031(2) 0.0003(17) C54 0.080(3) 0.079(3) 0.127(4) 0.010(3) 0.049(3) 0.010(2) C55 0.054(2) 0.107(3) 0.142(4) 0.058(3) 0.025(3) 0.016(2) C56 0.053(2) 0.195(6) 0.107(4) 0.086(4) 0.003(2) 0.011(3) C57 0.074(3) 0.171(5) 0.064(3) 0.056(3) 0.008(2) 0.006(3) C61 0.0569(17) 0.0506(15) 0.0428(15) 0.0161(12) 0.0091(12) 0.0059(12) C62 0.0512(16) 0.0679(18) 0.0523(16) 0.0280(14) 0.0150(13) 0.0096(13) C63 0.064(2) 0.081(2) 0.064(2) 0.0394(18) 0.0095(16) 0.0077(17) C64 0.112(4) 0.156(5) 0.112(4) 0.102(4) 0.023(3) 0.009(3) C65 0.117(4) 0.247(8) 0.172(6) 0.149(6) 0.066(4) 0.010(5) C66 0.097(4) 0.242(8) 0.201(7) 0.140(7) 0.079(4) 0.035(4) C67 0.069(2) 0.158(5) 0.135(4) 0.094(4) 0.044(3) 0.034(3) C71 0.0480(15) 0.0502(15) 0.0583(18) 0.0175(14) 0.0119(13) 0.0024(12) C72 0.0448(15) 0.0453(14) 0.0723(19) 0.0272(14) 0.0151(14) 0.0055(11) C73 0.067(2) 0.0523(18) 0.109(3) 0.0366(19) 0.041(2) 0.0133(15) C74 0.063(2) 0.084(3) 0.180(5) 0.082(3) 0.058(3) 0.030(2) C75 0.046(2) 0.108(4) 0.200(6) 0.098(4) 0.009(3) 0.005(2) C76 0.062(2) 0.085(3) 0.121(4) 0.040(3) -0.018(2) -0.016(2) C77 0.0537(18) 0.0577(18) 0.087(2) 0.0282(17) -0.0046(16) -0.0037(14) C81 0.0590(17) 0.0433(14) 0.0384(14) 0.0082(11) 0.0070(12) 0.0044(12) C82 0.0469(15) 0.0484(15) 0.0508(16) 0.0047(12) 0.0107(12) 0.0043(12) C83 0.059(2) 0.129(4) 0.100(3) -0.065(3) 0.002(2) 0.017(2) C84 0.068(3) 0.240(8) 0.163(5) -0.146(6) -0.019(3) 0.033(4) C85 0.083(3) 0.191(6) 0.152(5) -0.109(5) -0.001(3) 0.040(4) C86 0.064(2) 0.102(3) 0.102(3) -0.020(3) 0.017(2) 0.030(2) C87 0.0508(17) 0.0605(18) 0.065(2) 0.0090(15) 0.0081(15) 0.0063(14) _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 O2 1.9841(19) . ? Zn1 O1 1.990(2) . ? Zn1 N2 2.075(2) . ? Zn1 N3 2.166(2) . ? Zn1 N1 2.210(2) . ? Zn2 O10 1.948(2) . ? Zn2 O7 1.972(2) . ? Zn2 N5 2.059(2) . ? Zn2 N6 2.171(2) . ? Zn2 N4 2.186(2) . ? O1 C51 1.230(4) . ? O2 C61 1.291(3) . ? O3 C61 1.218(3) . ? O4 C51 1.269(4) . ? O5 C63 1.334(4) . ? O5 H5A 0.8200 . ? O6 C57 1.328(6) . ? O6 H6A 0.8200 . ? O7 C71 1.252(4) . ? O8 C71 1.243(4) . ? O9 C73 1.335(5) . ? O9 H9A 0.8200 . ? O10 C81 1.268(3) . ? O11 C81 1.243(3) . ? O12 C87 1.316(4) . ? O12 H12A 0.8200 . ? N1 C1 1.336(3) . ? N1 C5 1.336(3) . ? N2 C10 1.334(3) . ? N2 C6 1.334(3) . ? N3 C15 1.337(4) . ? N3 C11 1.341(3) . ? N4 C26 1.339(3) . ? N4 C22 1.342(3) . ? N5 C27 1.332(3) . ? N5 C31 1.338(3) . ? N6 C36 1.336(4) . ? N6 C32 1.345(3) . ? C1 C2 1.376(5) . ? C1 H1 0.9300 . ? C2 C3 1.364(5) . ? C2 H2 0.9300 . ? C3 C4 1.381(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.488(3) . ? C6 C7 1.381(3) . ? C7 C8 1.392(3) . ? C7 H7 0.9300 . ? C8 C9 1.395(3) . ? C8 C16 1.489(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.483(4) . ? C11 C12 1.385(4) . ? C12 C13 1.373(4) . ? C12 H12 0.9300 . ? C13 C14 1.365(5) . ? C13 H13 0.9300 . ? C14 C15 1.372(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.382(4) . ? C16 C17 1.387(4) . ? C17 C18 1.383(4) . ? C17 H17 0.9300 . ? C18 C19 1.353(5) . ? C18 H18 0.9300 . ? C19 C20 1.368(5) . ? C19 H19 0.9300 . ? C20 C21 1.381(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.364(5) . ? C22 H22 0.9300 . ? C23 C24 1.370(5) . ? C23 H23 0.9300 . ? C24 C25 1.375(4) . ? C24 H24 0.9300 . ? C25 C26 1.371(4) . ? C25 H25 0.9300 . ? C26 C27 1.488(3) . ? C27 C28 1.382(3) . ? C28 C29 1.395(3) . ? C28 H28 0.9300 . ? C29 C30 1.392(3) . ? C29 C37 1.483(3) . ? C30 C31 1.375(3) . ? C30 H30 0.9300 . ? C31 C32 1.481(3) . ? C32 C33 1.378(4) . ? C33 C34 1.383(4) . ? C33 H33 0.9300 . ? C34 C35 1.357(5) . ? C34 H34 0.9300 . ? C35 C36 1.370(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.384(4) . ? C37 C42 1.388(4) . ? C38 C39 1.386(4) . ? C38 H38 0.9300 . ? C39 C40 1.358(5) . ? C39 H39 0.9300 . ? C40 C41 1.370(5) . ? C40 H40 0.9300 . ? C41 C42 1.374(4) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C51 C52 1.498(4) . ? C52 C57 1.375(5) . ? C52 C53 1.400(5) . ? C53 C54 1.360(5) . ? C53 H53 0.9300 . ? C54 C55 1.363(6) . ? C54 H54 0.9300 . ? C55 C56 1.338(7) . ? C55 H55 0.9300 . ? C56 C57 1.417(6) . ? C56 H56 0.9300 . ? C61 C62 1.474(4) . ? C62 C67 1.362(5) . ? C62 C63 1.382(4) . ? C63 C64 1.390(5) . ? C64 C65 1.355(7) . ? C64 H64 0.9300 . ? C65 C66 1.361(8) . ? C65 H65 0.9300 . ? C66 C67 1.360(6) . ? C66 H66 0.9300 . ? C67 H67 0.9300 . ? C71 C72 1.492(4) . ? C72 C73 1.384(4) . ? C72 C77 1.400(4) . ? C73 C74 1.389(5) . ? C74 C75 1.344(7) . ? C74 H74 0.9300 . ? C75 C76 1.380(7) . ? C75 H75 0.9300 . ? C76 C77 1.381(5) . ? C76 H76 0.9300 . ? C77 H77 0.9300 . ? C81 C82 1.475(4) . ? C82 C83 1.366(5) . ? C82 C87 1.390(4) . ? C83 C84 1.373(5) . ? C83 H83 0.9300 . ? C84 C85 1.351(6) . ? C84 H84 0.9300 . ? C85 C86 1.337(6) . ? C85 H85 0.9300 . ? C86 C87 1.392(5) . ? C86 H86 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 O2 Zn1 O1 115.48(9) . . ? O2 Zn1 N2 138.18(8) . . ? O1 Zn1 N2 105.36(9) . . ? O2 Zn1 N3 103.28(9) . . ? O1 Zn1 N3 102.40(9) . . ? N2 Zn1 N3 75.16(8) . . ? O2 Zn1 N1 93.61(9) . . ? O1 Zn1 N1 93.53(9) . . ? N2 Zn1 N1 74.70(8) . . ? N3 Zn1 N1 148.69(8) . . ? O10 Zn2 O7 99.96(9) . . ? O10 Zn2 N5 140.83(9) . . ? O7 Zn2 N5 119.21(9) . . ? O10 Zn2 N6 100.31(9) . . ? O7 Zn2 N6 98.31(9) . . ? N5 Zn2 N6 75.02(8) . . ? O10 Zn2 N4 97.73(9) . . ? O7 Zn2 N4 101.77(9) . . ? N5 Zn2 N4 75.95(8) . . ? N6 Zn2 N4 150.15(8) . . ? C51 O1 Zn1 117.1(2) . . ? C61 O2 Zn1 109.90(17) . . ? C63 O5 H5A 109.5 . . ? C57 O6 H6A 109.5 . . ? C71 O7 Zn2 121.37(19) . . ? C73 O9 H9A 109.5 . . ? C81 O10 Zn2 120.89(18) . . ? C87 O12 H12A 109.5 . . ? C1 N1 C5 118.2(3) . . ? C1 N1 Zn1 126.3(2) . . ? C5 N1 Zn1 115.52(17) . . ? C10 N2 C6 120.4(2) . . ? C10 N2 Zn1 119.28(17) . . ? C6 N2 Zn1 120.18(16) . . ? C15 N3 C11 118.2(3) . . ? C15 N3 Zn1 125.6(2) . . ? C11 N3 Zn1 116.09(17) . . ? C26 N4 C22 118.5(2) . . ? C26 N4 Zn2 114.47(16) . . ? C22 N4 Zn2 127.0(2) . . ? C27 N5 C31 120.0(2) . . ? C27 N5 Zn2 119.21(16) . . ? C31 N5 Zn2 120.30(16) . . ? C36 N6 C32 118.5(3) . . ? C36 N6 Zn2 125.8(2) . . ? C32 N6 Zn2 115.69(16) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C6 114.6(2) . . ? C4 C5 C6 123.3(2) . . ? N2 C6 C7 121.3(2) . . ? N2 C6 C5 114.7(2) . . ? C7 C6 C5 124.0(2) . . ? C6 C7 C8 119.8(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 117.2(2) . . ? C7 C8 C16 121.0(2) . . ? C9 C8 C16 121.8(2) . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? N2 C10 C9 120.9(2) . . ? N2 C10 C11 114.5(2) . . ? C9 C10 C11 124.6(2) . . ? N3 C11 C12 121.5(3) . . ? N3 C11 C10 114.3(2) . . ? C12 C11 C10 124.2(2) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 118.6(3) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N3 C15 C14 123.0(3) . . ? N3 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C21 C16 C17 117.8(2) . . ? C21 C16 C8 121.5(2) . . ? C17 C16 C8 120.7(2) . . ? C18 C17 C16 121.1(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 120.2(3) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.8(3) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C16 120.4(3) . . ? C20 C21 H21 119.8 . . ? C16 C21 H21 119.8 . . ? N4 C22 C23 122.7(3) . . ? N4 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C24 118.3(3) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 118.9(3) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? N4 C26 C25 121.7(2) . . ? N4 C26 C27 115.1(2) . . ? C25 C26 C27 123.2(2) . . ? N5 C27 C28 121.2(2) . . ? N5 C27 C26 114.8(2) . . ? C28 C27 C26 124.0(2) . . ? C27 C28 C29 120.0(2) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 117.2(2) . . ? C30 C29 C37 122.3(2) . . ? C28 C29 C37 120.4(2) . . ? C31 C30 C29 120.0(2) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? N5 C31 C30 121.5(2) . . ? N5 C31 C32 113.5(2) . . ? C30 C31 C32 125.0(2) . . ? N6 C32 C33 121.6(2) . . ? N6 C32 C31 114.7(2) . . ? C33 C32 C31 123.7(2) . . ? C32 C33 C34 118.6(3) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 119.8(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C34 C35 C36 118.8(3) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? N6 C36 C35 122.6(3) . . ? N6 C36 H36 118.7 . . ? C35 C36 H36 118.7 . . ? C38 C37 C42 117.1(2) . . ? C38 C37 C29 122.3(2) . . ? C42 C37 C29 120.6(2) . . ? C37 C38 C39 121.4(3) . . ? C37 C38 H38 119.3 . . ? C39 C38 H38 119.3 . . ? C40 C39 C38 120.3(3) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? C39 C40 C41 119.3(3) . . ? C39 C40 H40 120.4 . . ? C41 C40 H40 120.4 . . ? C40 C41 C42 120.8(3) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? C41 C42 C37 121.1(3) . . ? C41 C42 H42 119.4 . . ? C37 C42 H42 119.4 . . ? O1 C51 O4 123.3(3) . . ? O1 C51 C52 118.9(3) . . ? O4 C51 C52 117.7(3) . . ? C57 C52 C53 117.7(3) . . ? C57 C52 C51 121.6(3) . . ? C53 C52 C51 120.7(3) . . ? C54 C53 C52 121.4(4) . . ? C54 C53 H53 119.3 . . ? C52 C53 H53 119.3 . . ? C53 C54 C55 119.1(4) . . ? C53 C54 H54 120.5 . . ? C55 C54 H54 120.5 . . ? C56 C55 C54 122.8(4) . . ? C56 C55 H55 118.6 . . ? C54 C55 H55 118.6 . . ? C55 C56 C57 118.2(4) . . ? C55 C56 H56 120.9 . . ? C57 C56 H56 120.9 . . ? O6 C57 C52 121.6(4) . . ? O6 C57 C56 117.7(4) . . ? C52 C57 C56 120.7(4) . . ? O3 C61 O2 121.9(3) . . ? O3 C61 C62 121.1(3) . . ? O2 C61 C62 117.0(2) . . ? C67 C62 C63 118.3(3) . . ? C67 C62 C61 118.9(3) . . ? C63 C62 C61 122.7(3) . . ? O5 C63 C62 121.9(3) . . ? O5 C63 C64 118.5(3) . . ? C62 C63 C64 119.6(4) . . ? C65 C64 C63 119.5(4) . . ? C65 C64 H64 120.3 . . ? C63 C64 H64 120.3 . . ? C64 C65 C66 121.5(4) . . ? C64 C65 H65 119.3 . . ? C66 C65 H65 119.3 . . ? C67 C66 C65 118.4(5) . . ? C67 C66 H66 120.8 . . ? C65 C66 H66 120.8 . . ? C66 C67 C62 122.6(4) . . ? C66 C67 H67 118.7 . . ? C62 C67 H67 118.7 . . ? O8 C71 O7 124.0(3) . . ? O8 C71 C72 118.9(3) . . ? O7 C71 C72 117.1(3) . . ? C73 C72 C77 118.7(3) . . ? C73 C72 C71 120.6(3) . . ? C77 C72 C71 120.6(3) . . ? O9 C73 C72 121.3(3) . . ? O9 C73 C74 118.0(4) . . ? C72 C73 C74 120.7(4) . . ? C75 C74 C73 119.4(4) . . ? C75 C74 H74 120.3 . . ? C73 C74 H74 120.3 . . ? C74 C75 C76 121.9(4) . . ? C74 C75 H75 119.1 . . ? C76 C75 H75 119.1 . . ? C75 C76 C77 119.3(4) . . ? C75 C76 H76 120.3 . . ? C77 C76 H76 120.3 . . ? C76 C77 C72 119.9(4) . . ? C76 C77 H77 120.0 . . ? C72 C77 H77 120.0 . . ? O11 C81 O10 123.2(3) . . ? O11 C81 C82 119.5(3) . . ? O10 C81 C82 117.3(2) . . ? C83 C82 C87 118.4(3) . . ? C83 C82 C81 119.4(3) . . ? C87 C82 C81 122.2(3) . . ? C82 C83 C84 120.4(4) . . ? C82 C83 H83 119.8 . . ? C84 C83 H83 119.8 . . ? C85 C84 C83 119.9(4) . . ? C85 C84 H84 120.0 . . ? C83 C84 H84 120.0 . . ? C86 C85 C84 122.0(4) . . ? C86 C85 H85 119.0 . . ? C84 C85 H85 119.0 . . ? C85 C86 C87 118.7(4) . . ? C85 C86 H86 120.6 . . ? C87 C86 H86 120.6 . . ? O12 C87 C82 122.0(3) . . ? O12 C87 C86 117.5(3) . . ? C82 C87 C86 120.5(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 O2 Zn1 O1 C51 54.9(3) . . . . ? N2 Zn1 O1 C51 -134.3(2) . . . . ? N3 Zn1 O1 C51 -56.5(2) . . . . ? N1 Zn1 O1 C51 150.6(2) . . . . ? O1 Zn1 O2 C61 172.62(18) . . . . ? N2 Zn1 O2 C61 6.0(3) . . . . ? N3 Zn1 O2 C61 -76.5(2) . . . . ? N1 Zn1 O2 C61 77.0(2) . . . . ? O10 Zn2 O7 C71 167.2(2) . . . . ? N5 Zn2 O7 C71 -12.3(3) . . . . ? N6 Zn2 O7 C71 65.1(2) . . . . ? N4 Zn2 O7 C71 -92.7(2) . . . . ? O7 Zn2 O10 C81 160.6(2) . . . . ? N5 Zn2 O10 C81 -20.1(3) . . . . ? N6 Zn2 O10 C81 -98.9(2) . . . . ? N4 Zn2 O10 C81 57.2(2) . . . . ? O2 Zn1 N1 C1 37.0(2) . . . . ? O1 Zn1 N1 C1 -78.8(2) . . . . ? N2 Zn1 N1 C1 176.2(2) . . . . ? N3 Zn1 N1 C1 160.1(2) . . . . ? O2 Zn1 N1 C5 -141.86(18) . . . . ? O1 Zn1 N1 C5 102.31(19) . . . . ? N2 Zn1 N1 C5 -2.66(17) . . . . ? N3 Zn1 N1 C5 -18.7(3) . . . . ? O2 Zn1 N2 C10 -100.9(2) . . . . ? O1 Zn1 N2 C10 91.62(19) . . . . ? N3 Zn1 N2 C10 -7.45(18) . . . . ? N1 Zn1 N2 C10 -178.90(19) . . . . ? O2 Zn1 N2 C6 83.2(2) . . . . ? O1 Zn1 N2 C6 -84.27(19) . . . . ? N3 Zn1 N2 C6 176.67(19) . . . . ? N1 Zn1 N2 C6 5.22(17) . . . . ? O2 Zn1 N3 C15 -39.9(3) . . . . ? O1 Zn1 N3 C15 80.4(2) . . . . ? N2 Zn1 N3 C15 -176.8(3) . . . . ? N1 Zn1 N3 C15 -160.7(2) . . . . ? O2 Zn1 N3 C11 143.40(18) . . . . ? O1 Zn1 N3 C11 -96.31(19) . . . . ? N2 Zn1 N3 C11 6.54(18) . . . . ? N1 Zn1 N3 C11 22.6(3) . . . . ? O10 Zn2 N4 C26 -145.92(18) . . . . ? O7 Zn2 N4 C26 112.15(18) . . . . ? N5 Zn2 N4 C26 -5.35(17) . . . . ? N6 Zn2 N4 C26 -19.1(3) . . . . ? O10 Zn2 N4 C22 36.5(2) . . . . ? O7 Zn2 N4 C22 -65.4(2) . . . . ? N5 Zn2 N4 C22 177.1(2) . . . . ? N6 Zn2 N4 C22 163.4(2) . . . . ? O10 Zn2 N5 C27 91.4(2) . . . . ? O7 Zn2 N5 C27 -89.35(18) . . . . ? N6 Zn2 N5 C27 179.41(19) . . . . ? N4 Zn2 N5 C27 6.44(17) . . . . ? O10 Zn2 N5 C31 -96.6(2) . . . . ? O7 Zn2 N5 C31 82.65(19) . . . . ? N6 Zn2 N5 C31 -8.60(17) . . . . ? N4 Zn2 N5 C31 178.44(19) . . . . ? O10 Zn2 N6 C36 -35.1(2) . . . . ? O7 Zn2 N6 C36 66.7(2) . . . . ? N5 Zn2 N6 C36 -175.2(3) . . . . ? N4 Zn2 N6 C36 -161.4(2) . . . . ? O10 Zn2 N6 C32 145.95(18) . . . . ? O7 Zn2 N6 C32 -112.26(18) . . . . ? N5 Zn2 N6 C32 5.86(17) . . . . ? N4 Zn2 N6 C32 19.7(3) . . . . ? C5 N1 C1 C2 0.1(4) . . . . ? Zn1 N1 C1 C2 -178.7(2) . . . . ? N1 C1 C2 C3 -0.5(5) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C1 N1 C5 C4 0.1(4) . . . . ? Zn1 N1 C5 C4 179.1(2) . . . . ? C1 N1 C5 C6 -178.8(2) . . . . ? Zn1 N1 C5 C6 0.2(3) . . . . ? C3 C4 C5 N1 0.1(4) . . . . ? C3 C4 C5 C6 178.9(3) . . . . ? C10 N2 C6 C7 -2.0(3) . . . . ? Zn1 N2 C6 C7 173.79(17) . . . . ? C10 N2 C6 C5 177.4(2) . . . . ? Zn1 N2 C6 C5 -6.8(3) . . . . ? N1 C5 C6 N2 4.1(3) . . . . ? C4 C5 C6 N2 -174.8(2) . . . . ? N1 C5 C6 C7 -176.5(2) . . . . ? C4 C5 C6 C7 4.6(4) . . . . ? N2 C6 C7 C8 -0.6(4) . . . . ? C5 C6 C7 C8 -180.0(2) . . . . ? C6 C7 C8 C9 2.8(3) . . . . ? C6 C7 C8 C16 -177.2(2) . . . . ? C7 C8 C9 C10 -2.6(3) . . . . ? C16 C8 C9 C10 177.5(2) . . . . ? C6 N2 C10 C9 2.3(4) . . . . ? Zn1 N2 C10 C9 -173.55(18) . . . . ? C6 N2 C10 C11 -176.9(2) . . . . ? Zn1 N2 C10 C11 7.2(3) . . . . ? C8 C9 C10 N2 0.0(4) . . . . ? C8 C9 C10 C11 179.2(2) . . . . ? C15 N3 C11 C12 -1.1(4) . . . . ? Zn1 N3 C11 C12 175.8(2) . . . . ? C15 N3 C11 C10 178.1(2) . . . . ? Zn1 N3 C11 C10 -5.0(3) . . . . ? N2 C10 C11 N3 -1.2(3) . . . . ? C9 C10 C11 N3 179.6(2) . . . . ? N2 C10 C11 C12 178.0(2) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? N3 C11 C12 C13 0.3(4) . . . . ? C10 C11 C12 C13 -178.9(3) . . . . ? C11 C12 C13 C14 0.7(5) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C11 N3 C15 C14 1.0(5) . . . . ? Zn1 N3 C15 C14 -175.6(3) . . . . ? C13 C14 C15 N3 -0.1(5) . . . . ? C7 C8 C16 C21 -2.4(4) . . . . ? C9 C8 C16 C21 177.6(3) . . . . ? C7 C8 C16 C17 176.8(2) . . . . ? C9 C8 C16 C17 -3.2(4) . . . . ? C21 C16 C17 C18 -0.7(4) . . . . ? C8 C16 C17 C18 -179.9(3) . . . . ? C16 C17 C18 C19 0.9(5) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C18 C19 C20 C21 0.4(5) . . . . ? C19 C20 C21 C16 -0.2(5) . . . . ? C17 C16 C21 C20 0.4(4) . . . . ? C8 C16 C21 C20 179.6(3) . . . . ? C26 N4 C22 C23 -1.4(4) . . . . ? Zn2 N4 C22 C23 176.1(2) . . . . ? N4 C22 C23 C24 -0.4(5) . . . . ? C22 C23 C24 C25 1.9(5) . . . . ? C23 C24 C25 C26 -1.6(5) . . . . ? C22 N4 C26 C25 1.7(4) . . . . ? Zn2 N4 C26 C25 -176.1(2) . . . . ? C22 N4 C26 C27 -178.5(2) . . . . ? Zn2 N4 C26 C27 3.8(3) . . . . ? C24 C25 C26 N4 -0.2(4) . . . . ? C24 C25 C26 C27 180.0(2) . . . . ? C31 N5 C27 C28 1.7(3) . . . . ? Zn2 N5 C27 C28 173.75(17) . . . . ? C31 N5 C27 C26 -178.5(2) . . . . ? Zn2 N5 C27 C26 -6.5(3) . . . . ? N4 C26 C27 N5 1.4(3) . . . . ? C25 C26 C27 N5 -178.7(2) . . . . ? N4 C26 C27 C28 -178.8(2) . . . . ? C25 C26 C27 C28 1.1(4) . . . . ? N5 C27 C28 C29 -3.6(4) . . . . ? C26 C27 C28 C29 176.6(2) . . . . ? C27 C28 C29 C30 2.9(3) . . . . ? C27 C28 C29 C37 -176.3(2) . . . . ? C28 C29 C30 C31 -0.4(3) . . . . ? C37 C29 C30 C31 178.7(2) . . . . ? C27 N5 C31 C30 0.8(3) . . . . ? Zn2 N5 C31 C30 -171.13(17) . . . . ? C27 N5 C31 C32 -178.4(2) . . . . ? Zn2 N5 C31 C32 9.7(3) . . . . ? C29 C30 C31 N5 -1.4(4) . . . . ? C29 C30 C31 C32 177.6(2) . . . . ? C36 N6 C32 C33 -0.1(4) . . . . ? Zn2 N6 C32 C33 178.91(19) . . . . ? C36 N6 C32 C31 178.1(2) . . . . ? Zn2 N6 C32 C31 -2.9(3) . . . . ? N5 C31 C32 N6 -4.0(3) . . . . ? C30 C31 C32 N6 176.9(2) . . . . ? N5 C31 C32 C33 174.2(2) . . . . ? C30 C31 C32 C33 -5.0(4) . . . . ? N6 C32 C33 C34 0.6(4) . . . . ? C31 C32 C33 C34 -177.4(2) . . . . ? C32 C33 C34 C35 0.0(5) . . . . ? C33 C34 C35 C36 -1.0(5) . . . . ? C32 N6 C36 C35 -1.0(4) . . . . ? Zn2 N6 C36 C35 -179.9(2) . . . . ? C34 C35 C36 N6 1.6(5) . . . . ? C30 C29 C37 C38 14.3(4) . . . . ? C28 C29 C37 C38 -166.6(3) . . . . ? C30 C29 C37 C42 -164.5(3) . . . . ? C28 C29 C37 C42 14.6(4) . . . . ? C42 C37 C38 C39 -0.7(5) . . . . ? C29 C37 C38 C39 -179.5(3) . . . . ? C37 C38 C39 C40 0.5(5) . . . . ? C38 C39 C40 C41 0.4(5) . . . . ? C39 C40 C41 C42 -1.2(5) . . . . ? C40 C41 C42 C37 1.0(5) . . . . ? C38 C37 C42 C41 -0.1(5) . . . . ? C29 C37 C42 C41 178.8(3) . . . . ? Zn1 O1 C51 O4 -4.6(5) . . . . ? Zn1 O1 C51 C52 173.7(2) . . . . ? O1 C51 C52 C57 -179.7(4) . . . . ? O4 C51 C52 C57 -1.4(5) . . . . ? O1 C51 C52 C53 -2.1(5) . . . . ? O4 C51 C52 C53 176.3(3) . . . . ? C57 C52 C53 C54 -1.7(6) . . . . ? C51 C52 C53 C54 -179.4(4) . . . . ? C52 C53 C54 C55 -1.2(6) . . . . ? C53 C54 C55 C56 3.3(8) . . . . ? C54 C55 C56 C57 -2.4(8) . . . . ? C53 C52 C57 O6 -178.1(5) . . . . ? C51 C52 C57 O6 -0.4(7) . . . . ? C53 C52 C57 C56 2.6(7) . . . . ? C51 C52 C57 C56 -179.7(4) . . . . ? C55 C56 C57 O6 180.0(5) . . . . ? C55 C56 C57 C52 -0.7(8) . . . . ? Zn1 O2 C61 O3 7.9(4) . . . . ? Zn1 O2 C61 C62 -171.3(2) . . . . ? O3 C61 C62 C67 4.7(5) . . . . ? O2 C61 C62 C67 -176.1(4) . . . . ? O3 C61 C62 C63 -175.3(3) . . . . ? O2 C61 C62 C63 3.9(5) . . . . ? C67 C62 C63 O5 177.1(4) . . . . ? C61 C62 C63 O5 -2.9(6) . . . . ? C67 C62 C63 C64 -3.6(6) . . . . ? C61 C62 C63 C64 176.4(4) . . . . ? O5 C63 C64 C65 -176.7(6) . . . . ? C62 C63 C64 C65 4.0(8) . . . . ? C63 C64 C65 C66 -1.0(11) . . . . ? C64 C65 C66 C67 -2.3(12) . . . . ? C65 C66 C67 C62 2.7(11) . . . . ? C63 C62 C67 C66 0.2(8) . . . . ? C61 C62 C67 C66 -179.7(5) . . . . ? Zn2 O7 C71 O8 13.2(4) . . . . ? Zn2 O7 C71 C72 -165.37(18) . . . . ? O8 C71 C72 C73 -1.5(4) . . . . ? O7 C71 C72 C73 177.2(3) . . . . ? O8 C71 C72 C77 -178.2(3) . . . . ? O7 C71 C72 C77 0.5(4) . . . . ? C77 C72 C73 O9 -180.0(3) . . . . ? C71 C72 C73 O9 3.2(5) . . . . ? C77 C72 C73 C74 1.2(5) . . . . ? C71 C72 C73 C74 -175.7(3) . . . . ? O9 C73 C74 C75 179.8(4) . . . . ? C72 C73 C74 C75 -1.2(5) . . . . ? C73 C74 C75 C76 0.9(6) . . . . ? C74 C75 C76 C77 -0.5(7) . . . . ? C75 C76 C77 C72 0.4(6) . . . . ? C73 C72 C77 C76 -0.7(5) . . . . ? C71 C72 C77 C76 176.1(3) . . . . ? Zn2 O10 C81 O11 10.2(4) . . . . ? Zn2 O10 C81 C82 -168.59(19) . . . . ? O11 C81 C82 C83 177.3(4) . . . . ? O10 C81 C82 C83 -3.8(5) . . . . ? O11 C81 C82 C87 -2.3(4) . . . . ? O10 C81 C82 C87 176.5(3) . . . . ? C87 C82 C83 C84 -0.1(9) . . . . ? C81 C82 C83 C84 -179.8(6) . . . . ? C82 C83 C84 C85 -0.7(13) . . . . ? C83 C84 C85 C86 1.9(15) . . . . ? C84 C85 C86 C87 -2.2(12) . . . . ? C83 C82 C87 O12 -178.8(4) . . . . ? C81 C82 C87 O12 0.9(5) . . . . ? C83 C82 C87 C86 -0.2(6) . . . . ? C81 C82 C87 C86 179.4(4) . . . . ? C85 C86 C87 O12 180.0(6) . . . . ? C85 C86 C87 C82 1.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.47 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.719 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.062 data_m3 _database_code_depnum_ccdc_archive 'CCDC 916060' #TrackingRef '6-M.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 N3 O6 Zn' _chemical_formula_sum 'C35 H25 N3 O6 Zn' _chemical_formula_weight 648.97 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 16.503(3) _cell_length_b 17.021(3) _cell_length_c 10.663(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.67(3) _cell_angle_gamma 90.00 _cell_volume 2952.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 15726 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 28.29 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.794 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15726 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3637 _reflns_number_gt 3096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SMART (Bruker, 2001)' _computing_publication_material 'SMART (Bruker, 2001)' _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^)+(0.0580P)^2^+0.9206P] 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 3637 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.0000 0.213603(13) 0.2500 0.04303(10) Uani 1 2 d S . . O1 O 0.05853(7) 0.13882(7) 0.15597(12) 0.0550(3) Uani 1 1 d . . . O2 O 0.14837(8) 0.23249(8) 0.13606(12) 0.0560(3) Uani 1 1 d . . . O5 O 0.32701(8) 0.10987(8) -0.15538(14) 0.0664(4) Uani 1 1 d . . . H5A H 0.3353 0.1573 -0.1501 0.100 Uiso 1 1 calc R . . N1 N 0.08621(9) 0.24626(9) 0.42230(13) 0.0487(3) Uani 1 1 d . . . N2 N 0.0000 0.33542(10) 0.2500 0.0358(3) Uani 1 2 d S . . C1 C 0.12833(14) 0.19657(12) 0.5064(2) 0.0651(5) Uani 1 1 d . . . H1 H 0.1206 0.1428 0.4938 0.078 Uiso 1 1 calc R . . C2 C 0.18256(16) 0.22195(14) 0.6106(2) 0.0757(6) Uani 1 1 d . . . H2 H 0.2114 0.1860 0.6670 0.091 Uiso 1 1 calc R . . C3 C 0.19337(15) 0.30068(15) 0.6299(2) 0.0750(6) Uani 1 1 d . . . H3 H 0.2296 0.3191 0.6999 0.090 Uiso 1 1 calc R . . C4 C 0.15010(12) 0.35286(12) 0.54458(16) 0.0584(4) Uani 1 1 d . . . H4 H 0.1568 0.4068 0.5564 0.070 Uiso 1 1 calc R . . C5 C 0.09660(9) 0.32357(9) 0.44132(14) 0.0423(3) Uani 1 1 d . . . C6 C 0.04652(8) 0.37431(8) 0.34424(13) 0.0367(3) Uani 1 1 d . . . C7 C 0.04673(9) 0.45536(8) 0.34800(13) 0.0394(3) Uani 1 1 d . . . H7 H 0.0781 0.4814 0.4160 0.047 Uiso 1 1 calc R . . C8 C 0.0000 0.49846(12) 0.2500 0.0371(4) Uani 1 2 d S . . C9 C 0.0000 0.58511(12) 0.2500 0.0415(4) Uani 1 2 d S . . C10 C -0.05205(13) 0.62784(10) 0.1594(2) 0.0669(6) Uani 1 1 d . . . H10 H -0.0877 0.6014 0.0967 0.080 Uiso 1 1 calc R . . C11 C -0.05202(16) 0.70887(11) 0.1606(2) 0.0770(7) Uani 1 1 d . . . H11 H -0.0881 0.7360 0.0994 0.092 Uiso 1 1 calc R . . C12 C 0.0000 0.74981(15) 0.2500 0.0690(8) Uani 1 2 d S . . H12 H 0.0000 0.8044 0.2500 0.083 Uiso 1 2 calc SR . . C13 C 0.11800(9) 0.16711(9) 0.10894(13) 0.0400(3) Uani 1 1 d . . . C14 C 0.15060(9) 0.11688(8) 0.01232(14) 0.0395(3) Uani 1 1 d . . . C15 C 0.10508(12) 0.05452(10) -0.04611(19) 0.0604(5) Uani 1 1 d . . . H15 H 0.0552 0.0411 -0.0221 0.072 Uiso 1 1 calc R . . C16 C 0.13406(15) 0.01222(11) -0.1404(2) 0.0713(6) Uani 1 1 d . . . H16 H 0.1030 -0.0290 -0.1807 0.086 Uiso 1 1 calc R . . C17 C 0.20862(13) 0.03088(10) -0.17496(18) 0.0590(4) Uani 1 1 d . . . H17 H 0.2282 0.0017 -0.2373 0.071 Uiso 1 1 calc R . . C18 C 0.25430(10) 0.09300(9) -0.11702(15) 0.0458(3) Uani 1 1 d . . . C19 C 0.22503(9) 0.13608(9) -0.02341(14) 0.0408(3) Uani 1 1 d . . . H19 H 0.2556 0.1780 0.0155 0.049 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 0.04967(16) 0.03540(14) 0.04571(16) 0.000 0.01289(11) 0.000 O1 0.0610(7) 0.0461(6) 0.0651(7) 0.0026(5) 0.0311(6) 0.0028(5) O2 0.0597(7) 0.0537(7) 0.0568(7) -0.0161(6) 0.0158(6) -0.0088(5) O5 0.0609(8) 0.0653(8) 0.0813(9) -0.0137(7) 0.0358(7) -0.0001(6) N1 0.0574(8) 0.0438(7) 0.0440(7) 0.0065(6) 0.0059(6) 0.0076(6) N2 0.0353(8) 0.0381(8) 0.0330(8) 0.000 0.0032(6) 0.000 C1 0.0811(13) 0.0544(10) 0.0583(11) 0.0165(9) 0.0070(10) 0.0179(9) C2 0.0856(15) 0.0785(15) 0.0574(12) 0.0236(10) -0.0045(11) 0.0254(11) C3 0.0738(13) 0.0897(16) 0.0520(11) 0.0103(10) -0.0170(10) 0.0107(11) C4 0.0598(10) 0.0625(11) 0.0462(9) 0.0033(8) -0.0106(8) 0.0025(8) C5 0.0414(7) 0.0463(8) 0.0381(7) 0.0043(6) 0.0031(6) 0.0048(6) C6 0.0352(6) 0.0416(7) 0.0330(7) 0.0013(5) 0.0045(5) 0.0009(5) C7 0.0409(7) 0.0403(7) 0.0344(7) -0.0030(5) -0.0014(5) -0.0023(6) C8 0.0370(9) 0.0390(10) 0.0354(9) 0.000 0.0068(7) 0.000 C9 0.0462(11) 0.0383(10) 0.0396(10) 0.000 0.0062(8) 0.000 C10 0.0812(13) 0.0424(9) 0.0657(12) 0.0044(8) -0.0204(10) 0.0016(9) C11 0.0975(17) 0.0439(10) 0.0797(15) 0.0126(9) -0.0138(13) 0.0079(9) C12 0.094(2) 0.0353(12) 0.0787(19) 0.000 0.0159(16) 0.000 C13 0.0414(7) 0.0418(7) 0.0364(7) 0.0048(6) 0.0048(6) 0.0067(6) C14 0.0457(7) 0.0347(7) 0.0385(7) 0.0045(5) 0.0083(6) 0.0033(6) C15 0.0666(11) 0.0456(9) 0.0748(12) -0.0073(8) 0.0289(9) -0.0157(8) C16 0.0915(15) 0.0458(9) 0.0816(14) -0.0220(9) 0.0287(12) -0.0224(9) C17 0.0821(12) 0.0408(8) 0.0591(10) -0.0091(7) 0.0264(9) 0.0015(8) C18 0.0517(8) 0.0404(7) 0.0471(8) 0.0028(6) 0.0137(7) 0.0066(6) C19 0.0404(7) 0.0405(7) 0.0409(7) -0.0009(6) 0.0045(6) 0.0028(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9708(12) . ? Zn1 O1 1.9708(12) 2 ? Zn1 N2 2.0735(17) . ? Zn1 N1 2.1979(16) . ? Zn1 N1 2.1979(16) 2 ? O1 C13 1.2696(18) . ? O2 C13 1.235(2) . ? O5 C18 1.362(2) . ? O5 H5A 0.8200 . ? N1 C5 1.338(2) . ? N1 C1 1.339(2) . ? N2 C6 1.3335(16) . ? N2 C6 1.3335(16) 2 ? C1 C2 1.374(3) . ? C1 H1 0.9300 . ? C2 C3 1.363(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.383(2) . ? C4 H4 0.9300 . ? C5 C6 1.4877(19) . ? C6 C7 1.380(2) . ? C7 C8 1.3979(18) . ? C7 H7 0.9300 . ? C8 C7 1.3979(18) 2 ? C8 C9 1.475(3) . ? C9 C10 1.386(2) 2 ? C9 C10 1.386(2) . ? C10 C11 1.379(2) . ? C10 H10 0.9300 . ? C11 C12 1.362(3) . ? C11 H11 0.9300 . ? C12 C11 1.362(3) 2 ? C12 H12 0.9300 . ? C13 C14 1.506(2) . ? C14 C19 1.385(2) . ? C14 C15 1.386(2) . ? C15 C16 1.386(3) . ? C15 H15 0.9300 . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 C18 1.383(2) . ? C17 H17 0.9300 . ? C18 C19 1.389(2) . ? C19 H19 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 O1 Zn1 O1 99.54(7) . 2 ? O1 Zn1 N2 130.23(3) . . ? O1 Zn1 N2 130.23(3) 2 . ? O1 Zn1 N1 106.55(5) . . ? O1 Zn1 N1 92.40(5) 2 . ? N2 Zn1 N1 75.35(4) . . ? O1 Zn1 N1 92.40(5) . 2 ? O1 Zn1 N1 106.55(5) 2 2 ? N2 Zn1 N1 75.35(4) . 2 ? N1 Zn1 N1 150.70(8) . 2 ? C13 O1 Zn1 115.68(10) . . ? C18 O5 H5A 109.5 . . ? C5 N1 C1 118.73(16) . . ? C5 N1 Zn1 115.08(10) . . ? C1 N1 Zn1 126.19(14) . . ? C6 N2 C6 120.48(17) . 2 ? C6 N2 Zn1 119.76(8) . . ? C6 N2 Zn1 119.76(8) 2 . ? N1 C1 C2 122.5(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.81(18) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.55(19) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.84(19) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.57(14) . . ? N1 C5 C6 115.05(12) . . ? C4 C5 C6 123.38(15) . . ? N2 C6 C7 121.09(13) . . ? N2 C6 C5 114.73(13) . . ? C7 C6 C5 124.18(13) . . ? C6 C7 C8 120.30(13) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C7 116.69(18) . 2 ? C7 C8 C9 121.65(9) . . ? C7 C8 C9 121.65(9) 2 . ? C10 C9 C10 116.7(2) 2 . ? C10 C9 C8 121.66(11) 2 . ? C10 C9 C8 121.66(11) . . ? C11 C10 C9 121.28(18) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 121.1(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C11 118.5(2) 2 . ? C11 C12 H12 120.8 2 . ? C11 C12 H12 120.8 . . ? O2 C13 O1 124.03(14) . . ? O2 C13 C14 119.63(13) . . ? O1 C13 C14 116.33(13) . . ? C19 C14 C15 119.73(14) . . ? C19 C14 C13 119.30(13) . . ? C15 C14 C13 120.87(14) . . ? C16 C15 C14 119.79(17) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 120.41(17) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.05(16) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? O5 C18 C17 117.96(15) . . ? O5 C18 C19 122.33(15) . . ? C17 C18 C19 119.71(15) . . ? C14 C19 C18 120.31(14) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? 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 O1 Zn1 O1 C13 -163.38(14) 2 . . . ? N2 Zn1 O1 C13 16.62(14) . . . . ? N1 Zn1 O1 C13 -67.97(12) . . . . ? N1 Zn1 O1 C13 89.40(12) 2 . . . ? O1 Zn1 N1 C5 127.64(11) . . . . ? O1 Zn1 N1 C5 -131.67(11) 2 . . . ? N2 Zn1 N1 C5 -0.58(10) . . . . ? N1 Zn1 N1 C5 -0.58(10) 2 . . . ? O1 Zn1 N1 C1 -51.75(17) . . . . ? O1 Zn1 N1 C1 48.94(16) 2 . . . ? N2 Zn1 N1 C1 -179.97(16) . . . . ? N1 Zn1 N1 C1 -179.97(16) 2 . . . ? O1 Zn1 N2 C6 -99.91(9) . . . . ? O1 Zn1 N2 C6 80.09(9) 2 . . . ? N1 Zn1 N2 C6 -0.44(8) . . . . ? N1 Zn1 N2 C6 179.56(8) 2 . . . ? O1 Zn1 N2 C6 80.09(9) . . . 2 ? O1 Zn1 N2 C6 -99.91(9) 2 . . 2 ? N1 Zn1 N2 C6 179.56(8) . . . 2 ? N1 Zn1 N2 C6 -0.44(8) 2 . . 2 ? C5 N1 C1 C2 -0.8(3) . . . . ? Zn1 N1 C1 C2 178.54(17) . . . . ? N1 C1 C2 C3 0.6(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C1 N1 C5 C4 0.6(2) . . . . ? Zn1 N1 C5 C4 -178.82(13) . . . . ? C1 N1 C5 C6 -179.17(16) . . . . ? Zn1 N1 C5 C6 1.39(16) . . . . ? C3 C4 C5 N1 -0.2(3) . . . . ? C3 C4 C5 C6 179.55(18) . . . . ? C6 N2 C6 C7 1.13(10) 2 . . . ? Zn1 N2 C6 C7 -178.87(10) . . . . ? C6 N2 C6 C5 -178.71(13) 2 . . . ? Zn1 N2 C6 C5 1.29(13) . . . . ? N1 C5 C6 N2 -1.75(17) . . . . ? C4 C5 C6 N2 178.46(14) . . . . ? N1 C5 C6 C7 178.41(14) . . . . ? C4 C5 C6 C7 -1.4(2) . . . . ? N2 C6 C7 C8 -2.3(2) . . . . ? C5 C6 C7 C8 177.57(11) . . . . ? C6 C7 C8 C7 1.09(10) . . . 2 ? C6 C7 C8 C9 -178.91(10) . . . . ? C7 C8 C9 C10 6.17(14) . . . 2 ? C7 C8 C9 C10 -173.83(14) 2 . . 2 ? C7 C8 C9 C10 -173.83(14) . . . . ? C7 C8 C9 C10 6.17(14) 2 . . . ? C10 C9 C10 C11 -0.42(19) 2 . . . ? C8 C9 C10 C11 179.58(19) . . . . ? C9 C10 C11 C12 0.9(4) . . . . ? C10 C11 C12 C11 -0.4(2) . . . 2 ? Zn1 O1 C13 O2 12.4(2) . . . . ? Zn1 O1 C13 C14 -166.21(9) . . . . ? O2 C13 C14 C19 14.4(2) . . . . ? O1 C13 C14 C19 -166.91(14) . . . . ? O2 C13 C14 C15 -162.01(16) . . . . ? O1 C13 C14 C15 16.6(2) . . . . ? C19 C14 C15 C16 -0.5(3) . . . . ? C13 C14 C15 C16 175.97(18) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? C15 C16 C17 C18 -1.2(3) . . . . ? C16 C17 C18 O5 -179.15(19) . . . . ? C16 C17 C18 C19 0.4(3) . . . . ? C15 C14 C19 C18 -0.2(2) . . . . ? C13 C14 C19 C18 -176.73(13) . . . . ? O5 C18 C19 C14 179.83(14) . . . . ? C17 C18 C19 C14 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.244 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.063