# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email gcguo@fjirsm.ac.cn _publ_contact_author_name 'Guo-Cong Guo' loop_ _publ_author_name 'Feng Luo' 'Ming-Sheng Wang' 'Pei-Xin Li' 'Guo-Cong Guo' 'Ming-Biao Luo' 'Gong-Ming Sun' 'Yu-Mei Song' data_1 _database_code_depnum_ccdc_archive 'CCDC 871159' #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H22 N4 O6 Zn' _chemical_formula_weight 623.91 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 Hexagonal _symmetry_space_group_name_H-M P6(4)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z' 'y, -x+y, z+1/3' 'x-y, x, z+2/3' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+1/3' '-x+y, y, -z' 'x, x-y, -z+2/3' _cell_length_a 16.5528(2) _cell_length_b 16.5528(2) _cell_length_c 25.5559(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6064.1(2) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5155 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 22.05 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.025 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8606 _exptl_absorpt_correction_T_max 0.8819 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29334 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3577 _reflns_number_gt 3149 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.036(19) _refine_ls_number_reflns 3577 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.714742(14) 0.285259(14) 0.1667 0.03577(10) Uani 1 2 d S . . O11 O 0.70854(13) 0.32692(12) 0.09491(7) 0.0514(5) Uani 1 1 d . . . O12 O 0.76452(14) 0.45786(15) 0.13801(8) 0.0651(6) Uani 1 1 d . . . C11 C 0.73955(18) 0.41345(19) 0.09639(10) 0.0444(7) Uani 1 1 d . . . C12 C 0.74690(18) 0.46322(17) 0.04607(10) 0.0443(7) Uani 1 1 d . . . C13 C 0.70774(11) 0.4155(2) 0.0000 0.0410(8) Uani 1 2 d S . . H13A H 0.6753 0.3506 0.0000 0.049 Uiso 1 2 calc SR . . C14 C 0.7943(3) 0.5592(2) 0.04587(14) 0.0789(12) Uani 1 1 d . . . H14A H 0.8201 0.5919 0.0767 0.095 Uiso 1 1 calc R . . C15 C 0.80348(16) 0.6070(3) 0.0000 0.105(2) Uani 1 2 d S . . H15A H 0.8359 0.6718 0.0000 0.125 Uiso 1 2 calc SR . . O21 O 0.5972(3) -0.12027(17) 0.02176(9) 0.1397(14) Uani 1 1 d . . . N21 N 0.66358(14) 0.14701(13) 0.14816(8) 0.0408(6) Uani 1 1 d . . . N22 N 0.56525(17) -0.13183(14) 0.10757(8) 0.0505(6) Uani 1 1 d . . . H22C H 0.5402 -0.1709 0.1329 0.061 Uiso 1 1 calc R . . C21 C 0.6541(2) 0.1209(2) 0.09865(11) 0.0634(10) Uani 1 1 d . . . H21A H 0.6694 0.1663 0.0731 0.076 Uiso 1 1 calc R . . C22 C 0.6231(3) 0.0313(2) 0.08261(11) 0.0706(11) Uani 1 1 d . . . H22A H 0.6200 0.0178 0.0471 0.085 Uiso 1 1 calc R . . C23 C 0.59617(19) -0.03956(17) 0.11924(10) 0.0433(7) Uani 1 1 d . . . C24 C 0.6025(2) -0.01316(19) 0.17047(11) 0.0584(8) Uani 1 1 d . . . H24A H 0.5834 -0.0578 0.1968 0.070 Uiso 1 1 calc R . . C25 C 0.6373(3) 0.0798(2) 0.18327(11) 0.0669(10) Uani 1 1 d . . . H25A H 0.6424 0.0957 0.2185 0.080 Uiso 1 1 calc R . . C26 C 0.5697(3) -0.16811(19) 0.06091(11) 0.0647(9) Uani 1 1 d . . . C27 C 0.5424(2) -0.26831(19) 0.05912(11) 0.0511(8) Uani 1 1 d . . . C28 C 0.5567(4) -0.3033(3) 0.01492(15) 0.1235(19) Uani 1 1 d . . . H28A H 0.5766 -0.2658 -0.0148 0.148 Uiso 1 1 calc R . . C29 C 0.5428(4) -0.3935(2) 0.01180(15) 0.1078(15) Uani 1 1 d . . . H29A H 0.5571 -0.4139 -0.0189 0.129 Uiso 1 1 calc R . . C30 C 0.5081(2) -0.45151(18) 0.05386(11) 0.0516(7) Uani 1 1 d . . . C31 C 0.4807(3) -0.4210(2) 0.09468(14) 0.0829(12) Uani 1 1 d . . . H31A H 0.4490 -0.4621 0.1219 0.099 Uiso 1 1 calc R . . C32 C 0.4983(3) -0.3288(2) 0.09796(14) 0.0743(10) Uani 1 1 d . . . H32A H 0.4792 -0.3097 0.1274 0.089 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 0.03822(11) 0.03822(11) 0.02760(17) -0.00215(15) -0.00215(15) 0.01666(15) O11 0.0664(10) 0.0483(10) 0.0331(9) 0.0056(8) -0.0075(8) 0.0238(8) O12 0.0733(11) 0.0842(13) 0.0401(11) -0.0208(10) -0.0193(9) 0.0412(10) C11 0.0449(12) 0.0522(14) 0.0353(13) -0.0086(11) -0.0095(11) 0.0237(11) C12 0.0516(13) 0.0406(12) 0.0424(14) -0.0064(10) -0.0151(12) 0.0243(10) C13 0.0460(14) 0.0289(17) 0.0423(18) 0.000 -0.0103(16) 0.0145(9) C14 0.107(3) 0.0400(15) 0.072(2) -0.0144(15) -0.048(2) 0.0227(17) C15 0.143(4) 0.029(2) 0.104(4) 0.000 -0.057(4) 0.0145(11) O21 0.318(4) 0.0593(13) 0.0430(12) 0.0148(11) 0.0389(19) 0.0955(18) N21 0.0506(12) 0.0328(10) 0.0352(11) 0.0004(8) 0.0018(9) 0.0179(9) N22 0.0765(14) 0.0361(11) 0.0383(12) 0.0101(9) 0.0160(11) 0.0278(10) C21 0.111(2) 0.0422(14) 0.0291(14) 0.0072(11) 0.0141(15) 0.0322(15) C22 0.132(3) 0.0432(15) 0.0317(15) 0.0015(12) 0.0076(16) 0.0405(16) C23 0.0571(14) 0.0325(12) 0.0395(14) 0.0059(11) 0.0114(12) 0.0218(10) C24 0.0924(18) 0.0406(13) 0.0387(14) 0.0084(13) 0.0088(15) 0.0306(13) C25 0.112(2) 0.0531(16) 0.0327(14) 0.0017(12) 0.0082(15) 0.0389(16) C26 0.114(2) 0.0399(14) 0.0405(16) 0.0079(12) 0.0151(17) 0.0388(15) C27 0.0749(17) 0.0415(13) 0.0402(15) 0.0029(12) 0.0089(14) 0.0316(12) C28 0.258(5) 0.061(2) 0.057(2) 0.0010(17) 0.014(3) 0.084(3) C29 0.210(4) 0.0576(18) 0.065(2) 0.0001(17) 0.023(3) 0.073(2) C30 0.0686(16) 0.0411(13) 0.0499(16) 0.0006(12) 0.0049(14) 0.0311(12) C31 0.132(3) 0.0512(17) 0.069(2) 0.0157(16) 0.030(2) 0.0481(18) C32 0.107(2) 0.0471(16) 0.073(2) 0.0077(16) 0.030(2) 0.0420(16) _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 O11 1.9799(18) 10_665 ? Zn1 O11 1.9799(18) . ? Zn1 N21 2.059(2) 10_665 ? Zn1 N21 2.059(2) . ? O11 C11 1.257(3) . ? O12 C11 1.240(3) . ? C11 C12 1.499(4) . ? C12 C14 1.376(4) . ? C12 C13 1.385(3) . ? C13 C12 1.385(3) 11_655 ? C13 H13A 0.9300 . ? C14 C15 1.379(4) . ? C14 H14A 0.9300 . ? C15 C14 1.379(4) 11_655 ? C15 H15A 0.9300 . ? O21 C26 1.215(4) . ? N21 C21 1.321(3) . ? N21 C25 1.322(4) . ? N22 C26 1.354(4) . ? N22 C23 1.379(3) . ? N22 H22C 0.8600 . ? C21 C22 1.367(4) . ? C21 H21A 0.9300 . ? C22 C23 1.389(4) . ? C22 H22A 0.9300 . ? C23 C24 1.368(4) . ? C24 C25 1.385(4) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 C27 1.486(4) . ? C27 C32 1.337(4) . ? C27 C28 1.343(5) . ? C28 C29 1.395(5) . ? C28 H28A 0.9300 . ? C29 C30 1.362(4) . ? C29 H29A 0.9300 . ? C30 C31 1.333(5) . ? C30 C30 1.490(6) 4_645 ? C31 C32 1.407(5) . ? C31 H31A 0.9300 . ? C32 H32A 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 O11 Zn1 O11 139.45(13) 10_665 . ? O11 Zn1 N21 96.33(8) 10_665 10_665 ? O11 Zn1 N21 108.06(8) . 10_665 ? O11 Zn1 N21 108.06(8) 10_665 . ? O11 Zn1 N21 96.33(8) . . ? N21 Zn1 N21 105.36(13) 10_665 . ? C11 O11 Zn1 107.82(16) . . ? O12 C11 O11 121.7(3) . . ? O12 C11 C12 119.9(3) . . ? O11 C11 C12 118.4(2) . . ? C14 C12 C13 119.3(3) . . ? C14 C12 C11 118.7(2) . . ? C13 C12 C11 122.0(2) . . ? C12 C13 C12 120.8(3) . 11_655 ? C12 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 11_655 . ? C12 C14 C15 120.1(3) . . ? C12 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 C14 120.5(4) . 11_655 ? C14 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 11_655 . ? C21 N21 C25 116.1(2) . . ? C21 N21 Zn1 119.93(18) . . ? C25 N21 Zn1 123.98(18) . . ? C26 N22 C23 127.6(2) . . ? C26 N22 H22C 116.2 . . ? C23 N22 H22C 116.2 . . ? N21 C21 C22 124.1(3) . . ? N21 C21 H21A 118.0 . . ? C22 C21 H21A 118.0 . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22A 119.9 . . ? C23 C22 H22A 119.9 . . ? C24 C23 N22 119.2(2) . . ? C24 C23 C22 115.7(2) . . ? N22 C23 C22 125.1(2) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24A 119.9 . . ? C25 C24 H24A 119.9 . . ? N21 C25 C24 123.6(3) . . ? N21 C25 H25A 118.2 . . ? C24 C25 H25A 118.2 . . ? O21 C26 N22 121.5(3) . . ? O21 C26 C27 120.6(3) . . ? N22 C26 C27 117.9(2) . . ? C32 C27 C28 116.7(3) . . ? C32 C27 C26 124.1(3) . . ? C28 C27 C26 119.1(3) . . ? C27 C28 C29 122.6(4) . . ? C27 C28 H28A 118.7 . . ? C29 C28 H28A 118.7 . . ? C30 C29 C28 119.7(4) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C31 C30 C29 117.0(3) . . ? C31 C30 C30 119.7(2) . 4_645 ? C29 C30 C30 123.0(2) . 4_645 ? C30 C31 C32 122.2(3) . . ? C30 C31 H31A 118.9 . . ? C32 C31 H31A 118.9 . . ? C27 C32 C31 120.5(3) . . ? C27 C32 H32A 119.7 . . ? C31 C32 H32A 119.7 . . ? 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 O11 Zn1 O11 C11 53.84(17) 10_665 . . . ? N21 Zn1 O11 C11 -70.2(2) 10_665 . . . ? N21 Zn1 O11 C11 -178.62(19) . . . . ? Zn1 O11 C11 O12 -2.5(3) . . . . ? Zn1 O11 C11 C12 176.9(2) . . . . ? O12 C11 C12 C14 9.7(4) . . . . ? O11 C11 C12 C14 -169.7(3) . . . . ? O12 C11 C12 C13 -170.4(2) . . . . ? O11 C11 C12 C13 10.2(4) . . . . ? C14 C12 C13 C12 0.4(3) . . . 11_655 ? C11 C12 C13 C12 -179.4(3) . . . 11_655 ? C13 C12 C14 C15 -0.9(5) . . . . ? C11 C12 C14 C15 179.0(3) . . . . ? C12 C14 C15 C14 0.4(3) . . . 11_655 ? O11 Zn1 N21 C21 157.7(2) 10_665 . . . ? O11 Zn1 N21 C21 10.5(3) . . . . ? N21 Zn1 N21 C21 -100.2(2) 10_665 . . . ? O11 Zn1 N21 C25 -21.2(3) 10_665 . . . ? O11 Zn1 N21 C25 -168.4(3) . . . . ? N21 Zn1 N21 C25 80.9(3) 10_665 . . . ? C25 N21 C21 C22 -2.8(5) . . . . ? Zn1 N21 C21 C22 178.2(3) . . . . ? N21 C21 C22 C23 2.2(6) . . . . ? C26 N22 C23 C24 -167.4(3) . . . . ? C26 N22 C23 C22 12.0(5) . . . . ? C21 C22 C23 C24 0.4(5) . . . . ? C21 C22 C23 N22 -179.0(3) . . . . ? N22 C23 C24 C25 177.1(3) . . . . ? C22 C23 C24 C25 -2.3(5) . . . . ? C21 N21 C25 C24 0.7(5) . . . . ? Zn1 N21 C25 C24 179.7(3) . . . . ? C23 C24 C25 N21 1.8(6) . . . . ? C23 N22 C26 O21 -5.7(6) . . . . ? C23 N22 C26 C27 172.6(3) . . . . ? O21 C26 C27 C32 -169.3(4) . . . . ? N22 C26 C27 C32 12.4(5) . . . . ? O21 C26 C27 C28 6.2(6) . . . . ? N22 C26 C27 C28 -172.1(4) . . . . ? C32 C27 C28 C29 -11.5(7) . . . . ? C26 C27 C28 C29 172.7(5) . . . . ? C27 C28 C29 C30 4.0(8) . . . . ? C28 C29 C30 C31 6.2(7) . . . . ? C28 C29 C30 C30 -179.5(5) . . . 4_645 ? C29 C30 C31 C32 -8.8(6) . . . . ? C30 C30 C31 C32 176.8(4) 4_645 . . . ? C28 C27 C32 C31 8.9(6) . . . . ? C26 C27 C32 C31 -175.5(4) . . . . ? C30 C31 C32 C27 1.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.351 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.065 # Attachment '1a.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 871160' #TrackingRef '1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H22 N4 O6 Zn' _chemical_formula_weight 623.91 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(2)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/3' '-y, x-y, z+2/3' '-x, -y, z' '-x+y, -x, z+1/3' 'y, -x+y, z+2/3' '-y, -x, -z+2/3' 'x-y, -y, -z' 'x, x-y, -z+1/3' 'y, x, -z+2/3' '-x+y, y, -z' '-x, -x+y, -z+1/3' _cell_length_a 16.5276(3) _cell_length_b 16.5276(3) _cell_length_c 25.3959(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6007.8(3) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2050 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 14.59 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.651 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8542 _exptl_absorpt_correction_T_max 0.8648 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30694 _diffrn_reflns_av_R_equivalents 0.1436 _diffrn_reflns_av_sigmaI/netI 0.1226 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3721 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1050P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0048(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 3721 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1659 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.2057 _refine_ls_wR_factor_gt 0.1626 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C11 C 0.5841(2) 0.3240(2) 0.07075(15) 0.0667(12) Uani 1 1 d . . . C12 C 0.5329(2) 0.2822(3) 0.12067(15) 0.0744(14) Uani 1 1 d . . . C13 C 0.5790(3) 0.28950(17) 0.1667 0.0626(14) Uani 1 2 d S . . H13 H 0.6440 0.3220 0.1667 0.075 Uiso 1 2 calc SR . . C14 C 0.4345(3) 0.2313(4) 0.11920(18) 0.129(2) Uani 1 1 d . . . H14 H 0.4024 0.2232 0.0878 0.155 Uiso 1 1 calc R . . C15 C 0.3859(5) 0.1929(2) 0.1667 0.161(4) Uani 1 2 d S . . H15 H 0.3209 0.1605 0.1667 0.193 Uiso 1 2 calc SR . . C27 C 1.2656(2) 0.8157(3) 0.10566(14) 0.0743(16) Uani 1 1 d . . . C26 C 1.1653(3) 0.7437(3) 0.10430(15) 0.101(2) Uani 1 1 d . . . C28 C 1.3251(3) 0.8313(4) 0.0693(2) 0.128(2) Uani 1 1 d . . . H28 H 1.3066 0.7925 0.0399 0.153 Uiso 1 1 calc R . . C29 C 1.4188(4) 0.9062(4) 0.0724(2) 0.153(3) Uani 1 1 d . . . H29 H 1.4582 0.9140 0.0444 0.184 Uiso 1 1 calc R . . C21 C 0.9156(3) 0.5540(3) -0.01640(15) 0.0861(17) Uani 1 1 d . . . H21 H 0.8995 0.5419 -0.0518 0.103 Uiso 1 1 calc R . . C22 C 1.0115(2) 0.6162(2) -0.00365(15) 0.0765(14) Uani 1 1 d . . . H22 H 1.0562 0.6413 -0.0302 0.092 Uiso 1 1 calc R . . C24 C 0.9646(3) 0.5947(3) 0.08326(16) 0.105(2) Uani 1 1 d . . . H24 H 0.9776 0.6087 0.1188 0.126 Uiso 1 1 calc R . . C23 C 1.0363(2) 0.6379(3) 0.04673(14) 0.0643(13) Uani 1 1 d . . . C31 C 1.3954(3) 0.9390(5) 0.1517(2) 0.174(3) Uani 1 1 d . . . H31 H 1.4167 0.9723 0.1830 0.209 Uiso 1 1 calc R . . C32 C 1.3024(4) 0.8637(5) 0.1486(2) 0.202(4) Uani 1 1 d . . . H32 H 1.2657 0.8475 0.1788 0.243 Uiso 1 1 calc R . . C30 C 1.4530(2) 0.9633(2) 0.11069(15) 0.0680(13) Uani 1 1 d . . . C25 C 0.8745(3) 0.5312(3) 0.06784(15) 0.0886(19) Uani 1 1 d . . . H25 H 0.8298 0.5000 0.0938 0.106 Uiso 1 1 calc R . . N21 N 0.84917(17) 0.51308(19) 0.01855(10) 0.0578(10) Uani 1 1 d . . . N22 N 1.12806(19) 0.7012(2) 0.05880(11) 0.0712(11) Uani 1 1 d . . . H22A H 1.1669 0.7153 0.0332 0.085 Uiso 1 1 calc R . . O11 O 0.66972(16) 0.37843(17) 0.07166(9) 0.0736(9) Uani 1 1 d . . . O12 O 0.53870(18) 0.30402(18) 0.02857(11) 0.0944(11) Uani 1 1 d . . . O21 O 1.1174(3) 0.7259(4) 0.14347(13) 0.211(3) Uani 1 1 d . . . Zn1 Zn 0.71295(2) 0.42591(4) 0.0000 0.05791(16) Uani 1 2 d S . . 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 C11 0.0709(17) 0.0651(16) 0.076(2) 0.0097(16) -0.0208(18) 0.0431(14) C12 0.0479(17) 0.076(2) 0.089(3) 0.027(2) -0.0096(18) 0.0234(16) C13 0.040(3) 0.058(2) 0.084(3) 0.017(3) 0.000 0.0200(14) C14 0.056(2) 0.163(4) 0.129(3) 0.075(3) -0.018(2) 0.024(3) C15 0.059(4) 0.210(7) 0.164(6) 0.078(7) 0.000 0.029(2) C27 0.054(2) 0.079(2) 0.056(2) -0.008(2) 0.0089(19) 0.0080(19) C26 0.053(2) 0.119(4) 0.066(3) -0.017(2) 0.014(2) -0.005(2) C28 0.085(3) 0.096(3) 0.128(4) -0.041(3) 0.016(3) -0.011(3) C29 0.080(3) 0.150(5) 0.148(4) -0.057(4) 0.017(3) -0.004(4) C21 0.073(2) 0.094(3) 0.058(2) -0.011(2) -0.006(2) 0.016(2) C22 0.0550(19) 0.080(2) 0.071(2) -0.001(2) 0.018(2) 0.0155(17) C24 0.071(3) 0.122(4) 0.062(2) -0.018(2) 0.008(2) 0.003(3) C23 0.0508(19) 0.070(2) 0.058(2) -0.0014(18) 0.0088(17) 0.0194(17) C31 0.080(4) 0.182(6) 0.140(4) -0.063(4) 0.014(3) -0.026(4) C32 0.086(4) 0.223(7) 0.107(4) -0.053(4) 0.018(3) -0.065(5) C30 0.0518(19) 0.0489(19) 0.089(2) -0.0096(19) 0.0006(19) 0.0144(14) C25 0.050(2) 0.099(3) 0.069(3) 0.001(2) 0.003(2) 0.002(2) N21 0.0517(15) 0.0566(15) 0.0572(18) -0.0013(14) 0.0055(13) 0.0212(12) N22 0.0533(15) 0.0717(18) 0.0680(19) -0.0002(17) 0.0185(16) 0.0158(14) O11 0.0569(13) 0.0856(14) 0.0694(15) 0.0124(12) -0.0025(12) 0.0289(11) O12 0.1076(17) 0.0910(16) 0.0880(19) 0.0029(14) -0.0312(15) 0.0523(13) O21 0.073(2) 0.274(5) 0.089(2) -0.057(3) 0.0224(19) -0.060(3) Zn1 0.0529(2) 0.0610(4) 0.0625(3) 0.000 -0.0058(3) 0.03049(19) _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 C11 O11 1.241(4) . ? C11 O12 1.254(4) . ? C11 C12 1.488(5) . ? C12 C13 1.366(4) . ? C12 C14 1.410(5) . ? C13 C12 1.366(4) 9 ? C13 H13 0.9300 . ? C14 C15 1.411(5) . ? C14 H14 0.9300 . ? C15 C14 1.411(5) 9 ? C15 H15 0.9300 . ? C27 C28 1.278(6) . ? C27 C32 1.307(6) . ? C27 C26 1.480(5) . ? C26 O21 1.212(5) . ? C26 N22 1.332(5) . ? C28 C29 1.421(6) . ? C28 H28 0.9300 . ? C29 C30 1.273(6) . ? C29 H29 0.9300 . ? C21 N21 1.307(4) . ? C21 C22 1.430(5) . ? C21 H21 0.9300 . ? C22 C23 1.337(5) . ? C22 H22 0.9300 . ? C24 C25 1.382(5) . ? C24 C23 1.388(5) . ? C24 H24 0.9300 . ? C23 N22 1.379(4) . ? C31 C30 1.330(6) . ? C31 C32 1.416(7) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C30 C30 1.414(6) 4_875 ? C25 N21 1.306(4) . ? C25 H25 0.9300 . ? N21 Zn1 2.030(2) . ? N22 H22A 0.8600 . ? O11 Zn1 1.969(2) . ? Zn1 O11 1.969(2) 11_655 ? Zn1 N21 2.030(2) 11_655 ? 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 O11 C11 O12 121.5(3) . . ? O11 C11 C12 119.9(3) . . ? O12 C11 C12 118.6(3) . . ? C13 C12 C14 120.1(4) . . ? C13 C12 C11 121.7(3) . . ? C14 C12 C11 118.2(3) . . ? C12 C13 C12 122.3(5) 9 . ? C12 C13 H13 118.9 9 . ? C12 C13 H13 118.9 . . ? C12 C14 C15 118.2(4) . . ? C12 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C14 C15 C14 120.9(6) 9 . ? C14 C15 H15 119.5 9 . ? C14 C15 H15 119.5 . . ? C28 C27 C32 113.7(4) . . ? C28 C27 C26 125.8(4) . . ? C32 C27 C26 120.1(4) . . ? O21 C26 N22 120.7(4) . . ? O21 C26 C27 120.6(4) . . ? N22 C26 C27 118.7(3) . . ? C27 C28 C29 121.9(5) . . ? C27 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? C30 C29 C28 125.1(5) . . ? C30 C29 H29 117.5 . . ? C28 C29 H29 117.5 . . ? N21 C21 C22 124.1(3) . . ? N21 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? C23 C22 C21 119.4(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C25 C24 C23 121.3(4) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.3 . . ? C22 C23 N22 119.3(3) . . ? C22 C23 C24 115.7(3) . . ? N22 C23 C24 125.0(3) . . ? C30 C31 C32 121.4(5) . . ? C30 C31 H31 119.3 . . ? C32 C31 H31 119.3 . . ? C27 C32 C31 123.4(5) . . ? C27 C32 H32 118.3 . . ? C31 C32 H32 118.3 . . ? C29 C30 C31 112.8(4) . . ? C29 C30 C30 121.7(4) . 4_875 ? C31 C30 C30 124.9(3) . 4_875 ? N21 C25 C24 123.1(3) . . ? N21 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C25 N21 C21 116.2(3) . . ? C25 N21 Zn1 120.0(2) . . ? C21 N21 Zn1 123.8(2) . . ? C26 N22 C23 129.5(3) . . ? C26 N22 H22A 115.3 . . ? C23 N22 H22A 115.3 . . ? C11 O11 Zn1 109.1(2) . . ? O11 Zn1 O11 139.63(15) . 11_655 ? O11 Zn1 N21 96.95(10) . . ? O11 Zn1 N21 107.64(12) 11_655 . ? O11 Zn1 N21 107.64(12) . 11_655 ? O11 Zn1 N21 96.95(9) 11_655 11_655 ? N21 Zn1 N21 104.16(18) . 11_655 ? 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 O11 C11 C12 C13 -11.0(6) . . . . ? O12 C11 C12 C13 170.1(3) . . . . ? O11 C11 C12 C14 171.3(5) . . . . ? O12 C11 C12 C14 -7.6(6) . . . . ? C14 C12 C13 C12 -1.7(4) . . . 9 ? C11 C12 C13 C12 -179.3(5) . . . 9 ? C13 C12 C14 C15 3.2(7) . . . . ? C11 C12 C14 C15 -179.0(4) . . . . ? C12 C14 C15 C14 -1.6(4) . . . 9 ? C28 C27 C26 O21 169.9(7) . . . . ? C32 C27 C26 O21 -3.1(10) . . . . ? C28 C27 C26 N22 -12.3(9) . . . . ? C32 C27 C26 N22 174.7(6) . . . . ? C32 C27 C28 C29 -11.0(10) . . . . ? C26 C27 C28 C29 175.7(6) . . . . ? C27 C28 C29 C30 0.9(11) . . . . ? N21 C21 C22 C23 -2.6(7) . . . . ? C21 C22 C23 N22 -177.1(4) . . . . ? C21 C22 C23 C24 1.7(7) . . . . ? C25 C24 C23 C22 1.9(8) . . . . ? C25 C24 C23 N22 -179.4(5) . . . . ? C28 C27 C32 C31 11.9(11) . . . . ? C26 C27 C32 C31 -174.3(7) . . . . ? C30 C31 C32 C27 -2.9(13) . . . . ? C28 C29 C30 C31 8.4(10) . . . . ? C28 C29 C30 C30 -179.5(6) . . . 4_875 ? C32 C31 C30 C29 -7.3(11) . . . . ? C32 C31 C30 C30 -179.1(7) . . . 4_875 ? C23 C24 C25 N21 -5.3(9) . . . . ? C24 C25 N21 C21 4.3(8) . . . . ? C24 C25 N21 Zn1 -175.5(4) . . . . ? C22 C21 N21 C25 -0.4(7) . . . . ? C22 C21 N21 Zn1 179.3(3) . . . . ? O21 C26 N22 C23 3.2(9) . . . . ? C27 C26 N22 C23 -174.6(4) . . . . ? C22 C23 N22 C26 168.4(5) . . . . ? C24 C23 N22 C26 -10.3(8) . . . . ? O12 C11 O11 Zn1 2.3(5) . . . . ? C12 C11 O11 Zn1 -176.6(3) . . . . ? C11 O11 Zn1 O11 -54.5(3) . . . 11_655 ? C11 O11 Zn1 N21 177.6(3) . . . . ? C11 O11 Zn1 N21 70.3(3) . . . 11_655 ? C25 N21 Zn1 O11 -11.1(4) . . . . ? C21 N21 Zn1 O11 169.1(4) . . . . ? C25 N21 Zn1 O11 -158.7(3) . . . 11_655 ? C21 N21 Zn1 O11 21.5(4) . . . 11_655 ? C25 N21 Zn1 N21 99.1(4) . . . 11_655 ? C21 N21 Zn1 N21 -80.7(4) . . . 11_655 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.311 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.068 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 871161' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H21 N4 O8 Zn' _chemical_formula_weight 654.90 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 Hexagonal _symmetry_space_group_name_H-M P6(4)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z' 'y, -x+y, z+1/3' 'x-y, x, z+2/3' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+1/3' '-x+y, y, -z' 'x, x-y, -z+2/3' _cell_length_a 16.5764(2) _cell_length_b 16.5764(2) _cell_length_c 25.3058(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6021.86(16) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4149 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 18.16 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2010 _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8801 _exptl_absorpt_correction_T_max 0.9081 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30578 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.1155 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3742 _reflns_number_gt 1938 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1024P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0105(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_ls_number_reflns 3742 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1754 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C23 C 0.3969(2) 1.03587(19) 0.11991(13) 0.0582(11) Uani 1 1 d . . . C11 C 0.2587(2) 0.5855(2) 0.09645(14) 0.0649(11) Uani 1 1 d . . . C24 C 0.3957(2) 1.0119(2) 0.17044(14) 0.0703(11) Uani 1 1 d . . . H24 H 0.4173 1.0572 0.1967 0.084 Uiso 1 1 calc R . . C30 C 0.4896(2) 1.45253(19) 0.05586(14) 0.0670(11) Uani 1 1 d . . . C12 C 0.2518(2) 0.5358(2) 0.04620(15) 0.0762(13) Uani 1 1 d . . . C27 C 0.4455(2) 1.2649(2) 0.06108(14) 0.0727(12) Uani 1 1 d . . . C13 C 0.29152(15) 0.5830(3) 0.0000 0.0616(13) Uani 1 2 d S . . H13 H 0.3239 0.6478 0.0000 0.074 Uiso 1 2 calc SR . . C21 C 0.3417(3) 0.8778(2) 0.09813(14) 0.0857(16) Uani 1 1 d . . . H21 H 0.3280 0.8333 0.0720 0.103 Uiso 1 1 calc R . . C28 C 0.4267(5) 1.3017(3) 0.0197(2) 0.211(3) Uani 1 1 d . . . H28 H 0.3980 1.2637 -0.0094 0.254 Uiso 1 1 calc R . . C25 C 0.3619(3) 0.9185(3) 0.18390(14) 0.0872(14) Uani 1 1 d . . . H25 H 0.3587 0.9027 0.2194 0.105 Uiso 1 1 calc R . . C26 C 0.4130(3) 1.1636(2) 0.06330(15) 0.0928(16) Uani 1 1 d . . . C32 C 0.4937(3) 1.3242(3) 0.0984(2) 0.1333(19) Uani 1 1 d . . . H32 H 0.5125 1.3039 0.1277 0.160 Uiso 1 1 calc R . . C14 C 0.2018(3) 0.4353(2) 0.04655(17) 0.1188(18) Uani 1 1 d . . . H14 H 0.1749 0.4018 0.0773 0.143 Uiso 1 1 calc R . . C22 C 0.3681(3) 0.9656(2) 0.08291(15) 0.0968(17) Uani 1 1 d . . . H22 H 0.3668 0.9789 0.0473 0.116 Uiso 1 1 calc R . . C29 C 0.4474(5) 1.3936(3) 0.0173(2) 0.200(3) Uani 1 1 d . . . H29 H 0.4307 1.4141 -0.0128 0.240 Uiso 1 1 calc R . . C31 C 0.5179(3) 1.4194(3) 0.0949(2) 0.137(2) Uani 1 1 d . . . H31 H 0.5553 1.4601 0.1212 0.165 Uiso 1 1 calc R . . C15 C 0.19575(17) 0.3915(3) 0.0000 0.145(3) Uani 1 2 d S . . N21 N 0.33434(16) 0.85141(16) 0.14797(10) 0.0560(9) Uani 1 1 d . . . N22 N 0.42478(19) 1.12810(17) 0.10807(10) 0.0672(10) Uani 1 1 d . . . H22A H 0.4535 1.1676 0.1329 0.081 Uiso 1 1 calc R . . O11 O 0.29166(15) 0.67113(14) 0.09514(9) 0.0699(8) Uani 1 1 d . . . O12 O 0.23213(16) 0.53997(18) 0.13864(11) 0.0946(10) Uani 1 1 d . . . O13 O 0.1566(12) 0.2966(3) -0.0011(6) 0.488(4) Uani 1 1 d . . . O21 O 0.3797(3) 1.1150(2) 0.02467(12) 0.1866(19) Uani 1 1 d . . . Zn1 Zn 0.285738(19) 0.714262(19) 0.1667 0.05339(14) Uani 1 2 d S . . 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 C23 0.0744(18) 0.0437(16) 0.052(2) -0.0045(14) -0.0149(16) 0.0264(13) C11 0.0592(15) 0.0665(17) 0.069(2) 0.0174(16) 0.0310(15) 0.0315(13) C24 0.0976(19) 0.0529(15) 0.060(2) -0.0117(17) -0.0122(19) 0.0371(14) C30 0.0717(17) 0.0478(14) 0.089(2) -0.0010(16) -0.0114(18) 0.0355(13) C12 0.081(2) 0.0578(18) 0.089(3) 0.0052(17) 0.0372(19) 0.0345(14) C27 0.118(2) 0.0514(15) 0.062(2) -0.0142(15) -0.0215(19) 0.0521(14) C13 0.064(2) 0.036(2) 0.076(3) 0.000 0.034(2) 0.0180(12) C21 0.141(3) 0.0536(18) 0.050(2) -0.0071(16) -0.014(2) 0.0393(19) C28 0.442(7) 0.083(3) 0.109(4) -0.018(2) -0.109(4) 0.131(3) C25 0.141(3) 0.087(2) 0.050(2) -0.0037(17) -0.009(2) 0.0690(18) C26 0.160(3) 0.0514(18) 0.062(2) -0.0170(17) -0.027(2) 0.0492(19) C32 0.178(3) 0.0655(19) 0.180(5) -0.020(3) -0.078(3) 0.0788(18) C14 0.159(3) 0.0458(19) 0.137(3) 0.020(2) 0.091(3) 0.040(2) C22 0.184(3) 0.0450(18) 0.051(2) 0.0027(16) -0.021(2) 0.049(2) C29 0.398(7) 0.076(2) 0.128(4) -0.009(2) -0.100(4) 0.121(3) C31 0.165(4) 0.064(2) 0.172(5) -0.019(3) -0.077(3) 0.049(2) C15 0.179(5) 0.016(3) 0.184(6) 0.000 0.103(5) 0.0078(13) N21 0.0642(14) 0.0463(13) 0.0552(18) 0.0014(12) -0.0011(13) 0.0260(10) N22 0.0971(16) 0.0447(13) 0.0578(17) -0.0144(13) -0.0192(15) 0.0340(12) O11 0.0871(12) 0.0558(11) 0.0645(14) 0.0030(10) 0.0233(11) 0.0341(9) O12 0.0984(14) 0.1056(16) 0.0902(19) 0.0329(13) 0.0393(13) 0.0588(12) O13 0.740(8) 0.171(3) 0.554(7) 0.205(5) 0.447(6) 0.228(5) O21 0.397(4) 0.0703(15) 0.0814(19) -0.0225(14) -0.089(2) 0.108(2) Zn1 0.05176(13) 0.05176(13) 0.0538(3) 0.0085(2) 0.0085(2) 0.02375(19) _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 C23 C24 1.336(5) . ? C23 C22 1.380(5) . ? C23 N22 1.391(4) . ? C11 O11 1.241(4) . ? C11 O12 1.253(4) . ? C11 C12 1.488(5) . ? C24 C25 1.400(5) . ? C24 H24 0.9300 . ? C30 C29 1.309(6) . ? C30 C31 1.326(6) . ? C30 C30 1.433(6) 4_685 ? C12 C13 1.377(4) . ? C12 C14 1.444(5) . ? C27 C32 1.309(6) . ? C27 C28 1.326(7) . ? C27 C26 1.485(5) . ? C13 C12 1.377(4) 11 ? C13 H13 0.9300 . ? C21 N21 1.320(4) . ? C21 C22 1.350(5) . ? C21 H21 0.9300 . ? C28 C29 1.386(7) . ? C28 H28 0.9300 . ? C25 N21 1.328(4) . ? C25 H25 0.9300 . ? C26 O21 1.210(4) . ? C26 N22 1.335(5) . ? C32 C31 1.422(6) . ? C32 H32 0.9300 . ? C14 C15 1.360(5) . ? C14 H14 0.9300 . ? C22 H22 0.9300 . ? C29 H29 0.9300 . ? C31 H31 0.9300 . ? C15 C14 1.360(5) 11 ? C15 O13 1.369(7) 11 ? C15 O13 1.369(7) . ? N21 Zn1 2.052(2) . ? N22 H22A 0.8600 . ? O11 Zn1 1.967(2) . ? O13 O13 0.28(4) 11 ? Zn1 O11 1.967(2) 10_665 ? Zn1 N21 2.052(2) 10_665 ? 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 C24 C23 C22 116.8(3) . . ? C24 C23 N22 118.7(3) . . ? C22 C23 N22 124.5(3) . . ? O11 C11 O12 122.2(3) . . ? O11 C11 C12 118.6(3) . . ? O12 C11 C12 119.2(3) . . ? C23 C24 C25 120.0(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C29 C30 C31 114.5(4) . . ? C29 C30 C30 124.4(3) . 4_685 ? C31 C30 C30 121.0(3) . 4_685 ? C13 C12 C14 119.8(4) . . ? C13 C12 C11 121.9(3) . . ? C14 C12 C11 118.3(3) . . ? C32 C27 C28 114.8(4) . . ? C32 C27 C26 124.2(4) . . ? C28 C27 C26 120.9(3) . . ? C12 C13 C12 121.1(4) . 11 ? C12 C13 H13 119.5 . . ? C12 C13 H13 119.5 11 . ? N21 C21 C22 123.8(3) . . ? N21 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C27 C28 C29 123.7(5) . . ? C27 C28 H28 118.2 . . ? C29 C28 H28 118.2 . . ? N21 C25 C24 122.6(3) . . ? N21 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? O21 C26 N22 120.7(4) . . ? O21 C26 C27 120.6(4) . . ? N22 C26 C27 118.7(3) . . ? C27 C32 C31 121.1(5) . . ? C27 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C15 C14 C12 117.2(4) . . ? C15 C14 H14 121.4 . . ? C12 C14 H14 121.4 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C30 C29 C28 122.3(5) . . ? C30 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C30 C31 C32 122.9(4) . . ? C30 C31 H31 118.5 . . ? C32 C31 H31 118.5 . . ? C14 C15 C14 125.0(5) . 11 ? C14 C15 O13 115.0(6) . 11 ? C14 C15 O13 119.8(6) 11 11 ? C14 C15 O13 119.8(6) . . ? C14 C15 O13 115.0(6) 11 . ? O13 C15 O13 11.7(16) 11 . ? C21 N21 C25 116.2(3) . . ? C21 N21 Zn1 120.5(2) . . ? C25 N21 Zn1 123.3(2) . . ? C26 N22 C23 128.8(3) . . ? C26 N22 H22A 115.6 . . ? C23 N22 H22A 115.6 . . ? C11 O11 Zn1 108.5(2) . . ? O13 O13 C15 84.1(8) 11 . ? O11 Zn1 O11 138.03(16) 10_665 . ? O11 Zn1 N21 97.32(10) 10_665 10_665 ? O11 Zn1 N21 108.44(9) . 10_665 ? O11 Zn1 N21 108.44(9) 10_665 . ? O11 Zn1 N21 97.32(10) . . ? N21 Zn1 N21 103.44(15) 10_665 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C22 C23 C24 C25 -3.1(6) . . . . ? N22 C23 C24 C25 175.6(3) . . . . ? O11 C11 C12 C13 8.6(5) . . . . ? O12 C11 C12 C13 -170.7(3) . . . . ? O11 C11 C12 C14 -171.5(4) . . . . ? O12 C11 C12 C14 9.2(6) . . . . ? C14 C12 C13 C12 0.3(3) . . . 11 ? C11 C12 C13 C12 -179.8(4) . . . 11 ? C32 C27 C28 C29 -6.2(10) . . . . ? C26 C27 C28 C29 173.8(6) . . . . ? C23 C24 C25 N21 3.3(6) . . . . ? C32 C27 C26 O21 -170.1(5) . . . . ? C28 C27 C26 O21 9.9(8) . . . . ? C32 C27 C26 N22 7.2(7) . . . . ? C28 C27 C26 N22 -172.8(5) . . . . ? C28 C27 C32 C31 3.7(8) . . . . ? C26 C27 C32 C31 -176.3(5) . . . . ? C13 C12 C14 C15 -0.7(6) . . . . ? C11 C12 C14 C15 179.4(4) . . . . ? N21 C21 C22 C23 5.6(7) . . . . ? C24 C23 C22 C21 -1.0(6) . . . . ? N22 C23 C22 C21 -179.6(4) . . . . ? C31 C30 C29 C28 5.6(9) . . . . ? C30 C30 C29 C28 -178.4(6) 4_685 . . . ? C27 C28 C29 C30 1.6(12) . . . . ? C29 C30 C31 C32 -8.1(8) . . . . ? C30 C30 C31 C32 175.7(5) 4_685 . . . ? C27 C32 C31 C30 3.6(9) . . . . ? C12 C14 C15 C14 0.3(3) . . . 11 ? C12 C14 C15 O13 -173.8(10) . . . 11 ? C12 C14 C15 O13 174.2(10) . . . . ? C22 C21 N21 C25 -5.4(6) . . . . ? C22 C21 N21 Zn1 176.1(4) . . . . ? C24 C25 N21 C21 1.0(6) . . . . ? C24 C25 N21 Zn1 179.4(3) . . . . ? O21 C26 N22 C23 -5.5(8) . . . . ? C27 C26 N22 C23 177.2(4) . . . . ? C24 C23 N22 C26 -164.4(4) . . . . ? C22 C23 N22 C26 14.2(7) . . . . ? O12 C11 O11 Zn1 -3.4(4) . . . . ? C12 C11 O11 Zn1 177.4(3) . . . . ? C14 C15 O13 O13 69(6) . . . 11 ? C14 C15 O13 O13 -117(6) 11 . . 11 ? C11 O11 Zn1 O11 55.9(2) . . . 10_665 ? C11 O11 Zn1 N21 -68.9(2) . . . 10_665 ? C11 O11 Zn1 N21 -175.8(2) . . . . ? C21 N21 Zn1 O11 158.3(3) . . . 10_665 ? C25 N21 Zn1 O11 -20.1(3) . . . 10_665 ? C21 N21 Zn1 O11 11.9(3) . . . . ? C25 N21 Zn1 O11 -166.5(3) . . . . ? C21 N21 Zn1 N21 -99.2(3) . . . 10_665 ? C25 N21 Zn1 N21 82.5(3) . . . 10_665 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.613 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.148 # Attachment '2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 871162' #TrackingRef '2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H21 N4 O7 Zn' _chemical_formula_weight 638.90 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(2)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/3' '-y, x-y, z+2/3' '-x, -y, z' '-x+y, -x, z+1/3' 'y, -x+y, z+2/3' '-y, -x, -z+2/3' 'x-y, -y, -z' 'x, x-y, -z+1/3' 'y, x, -z+2/3' '-x+y, y, -z' '-x, -x+y, -z+1/3' _cell_length_a 16.5744(2) _cell_length_b 16.5744(2) _cell_length_c 25.2582(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6009.1(2) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3190 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 17.81 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1962 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8536 _exptl_absorpt_correction_T_max 0.8804 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30481 _diffrn_reflns_av_R_equivalents 0.1316 _diffrn_reflns_av_sigmaI/netI 0.1194 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3725 _reflns_number_gt 1855 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.5000P] 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 SHELXL _refine_ls_extinction_coef 0.0005(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _refine_ls_number_reflns 3725 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1918 _refine_ls_wR_factor_gt 0.1659 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.919 _refine_ls_shift/su_max 0.004 _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 C11 C 0.4140(2) 0.6730(2) 0.07010(15) 0.0727(12) Uani 1 1 d . . . C12 C 0.4649(2) 0.7167(3) 0.12021(16) 0.0829(14) Uani 1 1 d . . . C13 C 0.4179(3) 0.70896(16) 0.1667 0.0719(14) Uani 1 2 d S . . H13 H 0.3531 0.6766 0.1667 0.086 Uiso 1 2 calc SR . . C14 C 0.5644(3) 0.7666(4) 0.12094(18) 0.135(2) Uani 1 1 d . . . H14 H 0.5978 0.7728 0.0901 0.162 Uiso 1 1 calc R . . C21 C 0.1229(3) 0.4626(3) 0.06905(15) 0.0952(19) Uani 1 1 d . . . H21 H 0.1680 0.4917 0.0951 0.114 Uiso 1 1 calc R . . C22 C 0.0341(2) 0.4011(3) 0.08498(16) 0.102(2) Uani 1 1 d . . . H22 H 0.0202 0.3871 0.1206 0.122 Uiso 1 1 calc R . . C23 C -0.03561(19) 0.3596(2) 0.04640(14) 0.0625(12) Uani 1 1 d . . . C24 C -0.0122(2) 0.3835(2) -0.00430(13) 0.0714(13) Uani 1 1 d . . . H24 H -0.0573 0.3602 -0.0307 0.086 Uiso 1 1 calc R . . C25 C 0.0817(3) 0.4445(3) -0.01680(14) 0.0861(16) Uani 1 1 d . . . H25 H 0.0974 0.4581 -0.0523 0.103 Uiso 1 1 calc R . . C26 C -0.1641(3) 0.2481(3) 0.10309(15) 0.0978(18) Uani 1 1 d . . . C27 C -0.2648(2) 0.1799(2) 0.10505(15) 0.0731(14) Uani 1 1 d . . . C15 C 0.6095(4) 0.80475(19) 0.1667 0.169(3) Uani 1 2 d S . . C32 C -0.3031(4) 0.1273(5) 0.1466(2) 0.214(4) Uani 1 1 d . . . H32 H -0.2665 0.1372 0.1765 0.256 Uiso 1 1 calc R . . C28 C -0.3239(3) 0.1705(3) 0.0689(2) 0.142(2) Uani 1 1 d . . . H28 H -0.3043 0.2094 0.0394 0.170 Uiso 1 1 calc R . . C29 C -0.4193(3) 0.1004(4) 0.0742(3) 0.155(3) Uani 1 1 d . . . H29 H -0.4608 0.1006 0.0496 0.186 Uiso 1 1 calc R . . C31 C -0.3952(4) 0.0580(5) 0.1480(2) 0.212(4) Uani 1 1 d . . . H31 H -0.4170 0.0238 0.1792 0.255 Uiso 1 1 calc R . . C30 C -0.4529(2) 0.0371(2) 0.11001(14) 0.0683(12) Uani 1 1 d . . . N21 N 0.14933(15) 0.48399(17) 0.01853(10) 0.0590(10) Uani 1 1 d . . . N22 N -0.12783(18) 0.29603(19) 0.05828(11) 0.0713(10) Uani 1 1 d . . . H22A H -0.1672 0.2860 0.0334 0.086 Uiso 1 1 calc R . . O12 O 0.32911(15) 0.62026(16) 0.07144(9) 0.0744(8) Uani 1 1 d . . . O11 O 0.46073(18) 0.69257(17) 0.02750(11) 0.1010(11) Uani 1 1 d . . . O21 O -0.1147(2) 0.2633(3) 0.14178(12) 0.187(2) Uani 1 1 d . . . O13 O 0.7038(3) 0.85191(15) 0.1667 0.245(3) Uani 1 2 d S . . Zn1 Zn 0.28567(2) 0.57134(4) 0.0000 0.05728(15) Uani 1 2 d S . . 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 C11 0.0686(17) 0.0641(16) 0.093(3) -0.0123(17) 0.0221(19) 0.0388(13) C12 0.0484(16) 0.078(2) 0.109(3) -0.038(2) 0.0078(18) 0.0221(15) C13 0.034(2) 0.070(2) 0.100(3) -0.048(3) 0.000 0.0169(12) C14 0.051(2) 0.143(3) 0.165(4) -0.077(3) 0.031(2) 0.013(2) C21 0.053(2) 0.122(4) 0.067(2) 0.006(2) -0.0078(19) 0.012(2) C22 0.050(2) 0.130(4) 0.060(2) 0.023(2) -0.0007(19) -0.005(2) C23 0.0375(16) 0.0651(19) 0.069(2) 0.0142(18) -0.0032(16) 0.0139(14) C24 0.0549(18) 0.0750(19) 0.060(2) 0.0052(19) -0.006(2) 0.0141(15) C25 0.084(2) 0.085(2) 0.062(2) 0.004(2) 0.001(2) 0.022(2) C26 0.056(2) 0.117(3) 0.071(2) 0.026(2) -0.015(2) 0.007(2) C27 0.0404(19) 0.068(2) 0.075(2) 0.007(2) -0.0122(18) 0.0003(16) C15 0.032(3) 0.212(5) 0.204(6) -0.153(5) 0.000 0.0160(16) C32 0.079(3) 0.241(7) 0.128(4) 0.065(5) -0.013(3) -0.065(4) C28 0.058(3) 0.087(3) 0.223(6) 0.054(4) -0.025(3) -0.007(2) C29 0.060(3) 0.125(4) 0.235(6) 0.070(4) -0.021(3) 0.012(3) C31 0.091(4) 0.243(7) 0.128(4) 0.082(4) 0.010(3) -0.047(5) C30 0.0478(18) 0.0508(18) 0.090(2) 0.0117(18) -0.0041(18) 0.0125(13) N21 0.0437(13) 0.0607(15) 0.0656(18) 0.0031(13) -0.0002(13) 0.0208(11) N22 0.0469(14) 0.0737(17) 0.0687(18) 0.0049(16) -0.0161(14) 0.0116(13) O12 0.0528(12) 0.0799(13) 0.0731(14) -0.0240(12) 0.0033(11) 0.0200(10) O11 0.1092(17) 0.0856(15) 0.1040(19) -0.0078(14) 0.0390(15) 0.0457(12) O21 0.074(2) 0.249(4) 0.0852(19) 0.056(2) -0.0246(18) -0.032(3) O13 0.035(2) 0.331(7) 0.270(6) -0.168(5) 0.000 0.0177(12) Zn1 0.0528(2) 0.0562(3) 0.0640(3) 0.000 0.0103(3) 0.02809(17) _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 C11 O12 1.231(4) . ? C11 O11 1.269(4) . ? C11 C12 1.492(5) . ? C12 C13 1.378(4) . ? C12 C14 1.428(5) . ? C13 C12 1.378(4) 9_565 ? C13 H13 0.9300 . ? C14 C15 1.349(5) . ? C14 H14 0.9300 . ? C21 N21 1.338(4) . ? C21 C22 1.366(5) . ? C21 H21 0.9300 . ? C22 C23 1.401(5) . ? C22 H22 0.9300 . ? C23 C24 1.340(5) . ? C23 N22 1.388(4) . ? C24 C25 1.404(5) . ? C24 H24 0.9300 . ? C25 N21 1.321(4) . ? C25 H25 0.9300 . ? C26 O21 1.217(5) . ? C26 N22 1.340(4) . ? C26 C27 1.476(5) . ? C27 C28 1.290(6) . ? C27 C32 1.307(6) . ? C15 C14 1.349(5) 9_565 ? C15 O13 1.354(7) . ? C32 C31 1.378(7) . ? C32 H32 0.9300 . ? C28 C29 1.425(6) . ? C28 H28 0.9300 . ? C29 C30 1.282(6) . ? C29 H29 0.9300 . ? C31 C30 1.275(6) . ? C31 H31 0.9300 . ? C30 C30 1.424(6) 4_455 ? N21 Zn1 2.037(2) . ? N22 H22A 0.8600 . ? O12 Zn1 1.962(2) . ? Zn1 O12 1.962(2) 11 ? Zn1 N21 2.037(2) 11 ? 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 O12 C11 O11 122.6(3) . . ? O12 C11 C12 119.3(3) . . ? O11 C11 C12 118.1(3) . . ? C13 C12 C14 118.6(4) . . ? C13 C12 C11 121.4(3) . . ? C14 C12 C11 120.0(3) . . ? C12 C13 C12 121.4(4) 9_565 . ? C12 C13 H13 119.3 9_565 . ? C12 C13 H13 119.3 . . ? C15 C14 C12 119.4(4) . . ? C15 C14 H14 120.3 . . ? C12 C14 H14 120.3 . . ? N21 C21 C22 124.5(3) . . ? N21 C21 H21 117.7 . . ? C22 C21 H21 117.7 . . ? C21 C22 C23 118.5(3) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C24 C23 N22 118.5(3) . . ? C24 C23 C22 118.3(3) . . ? N22 C23 C22 123.2(3) . . ? C23 C24 C25 118.7(3) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? N21 C25 C24 124.4(3) . . ? N21 C25 H25 117.8 . . ? C24 C25 H25 117.8 . . ? O21 C26 N22 119.9(3) . . ? O21 C26 C27 121.1(4) . . ? N22 C26 C27 118.9(3) . . ? C28 C27 C32 113.7(4) . . ? C28 C27 C26 124.6(4) . . ? C32 C27 C26 121.6(4) . . ? C14 C15 C14 122.6(5) 9_565 . ? C14 C15 O13 118.7(3) 9_565 . ? C14 C15 O13 118.7(3) . . ? C27 C32 C31 122.9(5) . . ? C27 C32 H32 118.6 . . ? C31 C32 H32 118.6 . . ? C27 C28 C29 119.8(5) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C30 C29 C28 125.9(5) . . ? C30 C29 H29 117.1 . . ? C28 C29 H29 117.1 . . ? C30 C31 C32 125.1(5) . . ? C30 C31 H31 117.5 . . ? C32 C31 H31 117.5 . . ? C31 C30 C29 110.4(4) . . ? C31 C30 C30 125.7(3) . 4_455 ? C29 C30 C30 123.2(4) . 4_455 ? C25 N21 C21 115.4(3) . . ? C25 N21 Zn1 124.1(2) . . ? C21 N21 Zn1 120.5(2) . . ? C26 N22 C23 129.1(3) . . ? C26 N22 H22A 115.5 . . ? C23 N22 H22A 115.5 . . ? C11 O12 Zn1 108.7(2) . . ? O12 Zn1 O12 138.06(14) . 11 ? O12 Zn1 N21 108.10(11) . 11 ? O12 Zn1 N21 97.46(9) 11 11 ? O12 Zn1 N21 97.46(9) . . ? O12 Zn1 N21 108.10(11) 11 . ? N21 Zn1 N21 104.03(17) 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 O12 C11 C12 C13 -8.4(6) . . . . ? O11 C11 C12 C13 171.1(3) . . . . ? O12 C11 C12 C14 170.7(4) . . . . ? O11 C11 C12 C14 -9.8(6) . . . . ? C14 C12 C13 C12 0.0(3) . . . 9_565 ? C11 C12 C13 C12 179.1(4) . . . 9_565 ? C13 C12 C14 C15 -0.1(7) . . . . ? C11 C12 C14 C15 -179.2(4) . . . . ? N21 C21 C22 C23 -2.6(8) . . . . ? C21 C22 C23 C24 -1.2(7) . . . . ? C21 C22 C23 N22 179.8(5) . . . . ? N22 C23 C24 C25 -177.1(4) . . . . ? C22 C23 C24 C25 3.9(6) . . . . ? C23 C24 C25 N21 -3.2(7) . . . . ? O21 C26 C27 C28 168.6(6) . . . . ? N22 C26 C27 C28 -9.1(8) . . . . ? O21 C26 C27 C32 -6.3(9) . . . . ? N22 C26 C27 C32 176.0(6) . . . . ? C12 C14 C15 C14 0.0(4) . . . 9_565 ? C12 C14 C15 O13 -180.0(4) . . . . ? C28 C27 C32 C31 9.9(11) . . . . ? C26 C27 C32 C31 -174.7(7) . . . . ? C32 C27 C28 C29 -6.5(9) . . . . ? C26 C27 C28 C29 178.3(5) . . . . ? C27 C28 C29 C30 -7.3(10) . . . . ? C27 C32 C31 C30 0.1(14) . . . . ? C32 C31 C30 C29 -12.7(11) . . . . ? C32 C31 C30 C30 176.9(7) . . . 4_455 ? C28 C29 C30 C31 16.2(9) . . . . ? C28 C29 C30 C30 -173.1(6) . . . 4_455 ? C24 C25 N21 C21 -0.4(6) . . . . ? C24 C25 N21 Zn1 179.3(3) . . . . ? C22 C21 N21 C25 3.3(7) . . . . ? C22 C21 N21 Zn1 -176.4(4) . . . . ? O21 C26 N22 C23 5.8(8) . . . . ? C27 C26 N22 C23 -176.5(4) . . . . ? C24 C23 N22 C26 165.3(5) . . . . ? C22 C23 N22 C26 -15.7(7) . . . . ? O11 C11 O12 Zn1 2.9(5) . . . . ? C12 C11 O12 Zn1 -177.6(3) . . . . ? C11 O12 Zn1 O12 -55.6(2) . . . 11 ? C11 O12 Zn1 N21 69.0(3) . . . 11 ? C11 O12 Zn1 N21 176.5(3) . . . . ? C25 N21 Zn1 O12 166.5(3) . . . . ? C21 N21 Zn1 O12 -13.8(3) . . . . ? C25 N21 Zn1 O12 20.2(4) . . . 11 ? C21 N21 Zn1 O12 -160.1(3) . . . 11 ? C25 N21 Zn1 N21 -82.7(3) . . . 11 ? C21 N21 Zn1 N21 97.0(3) . . . 11 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.497 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.077 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 871163' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H23 N5 O6 Zn' _chemical_formula_weight 638.92 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 Hexagonal _symmetry_space_group_name_H-M P6(4)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z' 'y, -x+y, z+1/3' 'x-y, x, z+2/3' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+1/3' '-x+y, y, -z' 'x, x-y, -z+2/3' _cell_length_a 16.5764(3) _cell_length_b 16.5764(3) _cell_length_c 25.2504(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6008.7(3) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6809 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 20.90 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8806 _exptl_absorpt_correction_T_max 0.9085 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30059 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3733 _reflns_number_gt 2905 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1316P)^2^+0.4604P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 3733 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1979 _refine_ls_wR_factor_gt 0.1785 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.006 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 C11 C 0.25850(15) 0.67337(15) 0.06963(10) 0.0721(7) Uani 1 1 d . . . C12 C 0.25094(15) 0.71598(14) 0.12080(11) 0.0825(8) Uani 1 1 d . . . C13 C 0.29116(10) 0.70884(10) 0.1667 0.0721(9) Uani 1 2 d S . . H13 H 0.3236 0.6764 0.1667 0.087 Uiso 1 2 calc SR . . C14 C 0.20428(15) 0.76661(18) 0.12060(14) 0.1441(10) Uani 1 1 d . . . H14 H 0.1796 0.7742 0.0892 0.173 Uiso 1 1 calc R . . C15 C 0.19464(14) 0.80536(14) 0.1667 0.1677(15) Uani 1 2 d S . . C21 C 0.36159(17) 0.44445(17) -0.01760(9) 0.0782(8) Uani 1 1 d . . . H21 H 0.3583 0.4574 -0.0531 0.094 Uiso 1 1 calc R . . C22 C 0.39514(15) 0.38438(15) -0.00485(9) 0.0728(7) Uani 1 1 d . . . H22 H 0.4170 0.3615 -0.0315 0.087 Uiso 1 1 calc R . . C23 C 0.39577(14) 0.35930(13) 0.04675(9) 0.0620(7) Uani 1 1 d . . . C24 C 0.36474(16) 0.39946(16) 0.08479(10) 0.0963(8) Uani 1 1 d . . . H24 H 0.3633 0.3850 0.1205 0.116 Uiso 1 1 calc R . . C25 C 0.33659(17) 0.46040(17) 0.06838(10) 0.0915(8) Uani 1 1 d . . . H25 H 0.3177 0.4875 0.0942 0.110 Uiso 1 1 calc R . . C26 C 0.41176(18) 0.24851(17) 0.10297(10) 0.0929(8) Uani 1 1 d . . . C27 C 0.44414(16) 0.17873(15) 0.10518(10) 0.0750(7) Uani 1 1 d . . . C28 C 0.4942(2) 0.17007(19) 0.07038(17) 0.1310(13) Uani 1 1 d . . . H28 H 0.5148 0.2109 0.0418 0.157 Uiso 1 1 calc R . . C29 C 0.5197(2) 0.1018(2) 0.07326(19) 0.1428(15) Uani 1 1 d . . . H29 H 0.5605 0.1018 0.0480 0.171 Uiso 1 1 calc R . . C30 C 0.48838(15) 0.03728(14) 0.11031(10) 0.0673(7) Uani 1 1 d . . . C31 C 0.4455(2) 0.0527(2) 0.14736(16) 0.2094(12) Uani 1 1 d . . . H31 H 0.4258 0.0131 0.1765 0.251 Uiso 1 1 calc R . . C32 C 0.4271(3) 0.1245(2) 0.14647(15) 0.2130(13) Uani 1 1 d . . . H32 H 0.4014 0.1354 0.1765 0.256 Uiso 1 1 calc R . . N21 N 0.33445(11) 0.48346(11) 0.01812(7) 0.0607(5) Uani 1 1 d . . . N22 N 0.42469(6) 0.29695(2) 0.05803(4) 0.0670(5) Uani 1 1 d . . . H22A H 0.4548 0.2876 0.0333 0.080 Uiso 1 1 calc R . . N11 N 0.14571(6) 0.85396(2) 0.16667(4) 0.2236(19) Uani 1 2 d SR . . H11A H 0.1397 0.8780 0.1956 0.268 Uiso 0.50 1 calc PR . . H11B H 0.1216 0.8598 0.1378 0.268 Uiso 0.50 1 calc PR . . O11 O 0.29071(6) 0.62064(2) 0.07173(4) 0.0765(5) Uani 1 1 d R . . O12 O 0.23239(6) 0.69234(2) 0.02760(4) 0.1005(7) Uani 1 1 d R . . O21 O 0.37875(6) 0.26358(2) 0.14157(4) 0.1986(7) Uani 1 1 d R . . Zn1 Zn 0.28593(6) 0.57195(2) 0.00001(4) 0.05577(9) Uani 1 2 d SR . . 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 C11 0.0648(10) 0.0627(10) 0.0915(15) -0.0215(10) -0.0389(10) 0.0340(8) C12 0.0781(9) 0.0700(10) 0.1166(17) -0.0414(11) -0.0522(11) 0.0500(7) C13 0.0691(7) 0.0691(7) 0.097(2) -0.0312(15) -0.0312(15) 0.0484(9) C14 0.1661(11) 0.1496(12) 0.197(2) -0.0933(15) -0.1263(14) 0.1395(8) C15 0.2055(10) 0.2055(10) 0.203(4) -0.129(3) -0.129(3) 0.1855(12) C21 0.1057(13) 0.0870(12) 0.0595(13) 0.0039(10) 0.0037(11) 0.0612(9) C22 0.0931(11) 0.0784(10) 0.0650(13) 0.0010(11) 0.0129(11) 0.0566(8) C23 0.0773(10) 0.0623(9) 0.0620(12) 0.0053(9) 0.0123(9) 0.0468(7) C24 0.1771(14) 0.1246(11) 0.0542(13) 0.0167(10) 0.0186(11) 0.1256(9) C25 0.1536(12) 0.1167(11) 0.0632(14) 0.0000(10) 0.0122(12) 0.1119(8) C26 0.1529(13) 0.1090(11) 0.0703(15) 0.0079(10) 0.0194(13) 0.1055(8) C27 0.1075(12) 0.0746(9) 0.0703(14) 0.0076(9) 0.0156(11) 0.0660(8) C28 0.1573(18) 0.0840(12) 0.188(3) 0.0576(16) 0.074(2) 0.0873(11) C29 0.1275(15) 0.1140(15) 0.229(4) 0.064(2) 0.076(2) 0.0922(11) C30 0.0680(10) 0.0447(8) 0.0933(15) 0.0045(10) 0.0079(11) 0.0313(7) C31 0.425(2) 0.2592(15) 0.125(2) 0.0834(16) 0.090(2) 0.3073(11) C32 0.445(2) 0.2612(17) 0.112(2) 0.0812(16) 0.101(2) 0.3108(13) N21 0.0695(8) 0.0637(8) 0.0622(10) 0.0059(7) 0.0004(8) 0.0434(6) N22 0.0851(8) 0.0707(8) 0.0689(10) -0.0003(8) 0.0107(9) 0.0567(6) N11 0.2935(10) 0.2935(10) 0.248(5) -0.124(5) -0.124(5) 0.2702(12) O11 0.0903(8) 0.0821(8) 0.0728(9) -0.0237(7) -0.0294(7) 0.0549(6) O12 0.1058(10) 0.0870(10) 0.1023(13) -0.0044(9) -0.0471(10) 0.0433(8) O21 0.4233(14) 0.2560(10) 0.0953(12) 0.0700(9) 0.1017(12) 0.3039(8) Zn1 0.05101(12) 0.05584(19) 0.06208(17) 0.000 -0.01006(14) 0.02792(10) _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 C11 O11 1.232(3) . ? C11 O12 1.244(3) . ? C11 C12 1.507(4) . ? C12 C13 1.371(3) . ? C12 C14 1.397(4) . ? C13 C12 1.371(3) 10_665 ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C14 1.376(4) 10_665 ? C15 N11 1.400(4) . ? C21 N21 1.313(3) . ? C21 C22 1.399(4) . ? C21 H21 0.9300 . ? C22 C23 1.369(3) . ? C22 H22 0.9300 . ? C23 N22 1.369(3) . ? C23 C24 1.404(4) . ? C24 C25 1.371(4) . ? C24 H24 0.9300 . ? C25 N21 1.331(3) . ? C25 H25 0.9300 . ? C26 O21 1.203(3) . ? C26 N22 1.344(3) . ? C26 C27 1.500(4) . ? C27 C28 1.265(5) . ? C27 C32 1.312(4) . ? C28 C29 1.394(5) . ? C28 H28 0.9300 . ? C29 C30 1.316(5) . ? C29 H29 0.9300 . ? C30 C31 1.275(5) . ? C30 C30 1.467(5) 4_655 ? C31 C32 1.369(6) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N21 Zn1 2.046(2) . ? N22 H22A 0.8600 . ? N11 H11A 0.8600 . ? N11 H11B 0.8600 . ? O11 Zn1 1.9682 . ? Zn1 O11 1.9688(18) 11 ? Zn1 N21 2.045(2) 11 ? 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 O11 C11 O12 123.0(2) . . ? O11 C11 C12 117.5(2) . . ? O12 C11 C12 119.5(2) . . ? C13 C12 C14 119.6(3) . . ? C13 C12 C11 121.7(2) . . ? C14 C12 C11 118.6(3) . . ? C12 C13 C12 120.5(3) 10_665 . ? C12 C13 H13 119.7 10_665 . ? C12 C13 H13 119.7 . . ? C15 C14 C12 120.4(3) . . ? C15 C14 H14 119.8 . . ? C12 C14 H14 119.8 . . ? C14 C15 C14 119.4(4) 10_665 . ? C14 C15 N11 120.3(2) 10_665 . ? C14 C15 N11 120.30(19) . . ? N21 C21 C22 123.2(2) . . ? N21 C21 H21 118.4 . . ? C22 C21 H21 118.4 . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? N22 C23 C22 119.1(2) . . ? N22 C23 C24 124.4(2) . . ? C22 C23 C24 116.5(2) . . ? C25 C24 C23 118.9(2) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? N21 C25 C24 124.6(3) . . ? N21 C25 H25 117.7 . . ? C24 C25 H25 117.7 . . ? O21 C26 N22 120.9(3) . . ? O21 C26 C27 120.3(2) . . ? N22 C26 C27 118.7(2) . . ? C28 C27 C32 113.8(3) . . ? C28 C27 C26 124.7(3) . . ? C32 C27 C26 121.4(3) . . ? C27 C28 C29 122.6(4) . . ? C27 C28 H28 118.7 . . ? C29 C28 H28 118.7 . . ? C30 C29 C28 122.7(4) . . ? C30 C29 H29 118.7 . . ? C28 C29 H29 118.6 . . ? C31 C30 C29 113.0(3) . . ? C31 C30 C30 125.2(2) . 4_655 ? C29 C30 C30 121.4(3) . 4_655 ? C30 C31 C32 123.4(3) . . ? C30 C31 H31 118.3 . . ? C32 C31 H31 118.3 . . ? C27 C32 C31 122.9(4) . . ? C27 C32 H32 118.5 . . ? C31 C32 H32 118.5 . . ? C21 N21 C25 116.6(2) . . ? C21 N21 Zn1 123.62(17) . . ? C25 N21 Zn1 119.70(19) . . ? C26 N22 C23 127.95(18) . . ? C26 N22 H22A 116.0 . . ? C23 N22 H22A 116.0 . . ? C15 N11 H11A 120.0 . . ? C15 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C11 O11 Zn1 107.96(13) . . ? O11 Zn1 O11 138.4 11 . ? O11 Zn1 N21 107.56(9) 11 . ? O11 Zn1 N21 97.97(6) . . ? O11 Zn1 N21 97.98(8) 11 11 ? O11 Zn1 N21 107.62(6) . 11 ? N21 Zn1 N21 103.23(8) . 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 O11 C11 C12 C13 10.0(3) . . . . ? O12 C11 C12 C13 -170.05(15) . . . . ? O11 C11 C12 C14 -172.19(18) . . . . ? O12 C11 C12 C14 7.7(3) . . . . ? C14 C12 C13 C12 1.57(14) . . . 10_665 ? C11 C12 C13 C12 179.3(2) . . . 10_665 ? C13 C12 C14 C15 -3.2(3) . . . . ? C11 C12 C14 C15 178.99(16) . . . . ? C12 C14 C15 C14 1.58(14) . . . 10_665 ? C12 C14 C15 N11 -178.29(14) . . . . ? N21 C21 C22 C23 3.9(3) . . . . ? C21 C22 C23 N22 176.88(17) . . . . ? C21 C22 C23 C24 -2.2(3) . . . . ? N22 C23 C24 C25 -179.31(18) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C23 C24 C25 N21 1.5(3) . . . . ? O21 C26 C27 C28 -166.7(3) . . . . ? N22 C26 C27 C28 10.0(4) . . . . ? O21 C26 C27 C32 8.5(4) . . . . ? N22 C26 C27 C32 -174.8(2) . . . . ? C32 C27 C28 C29 6.9(5) . . . . ? C26 C27 C28 C29 -177.6(3) . . . . ? C27 C28 C29 C30 4.8(6) . . . . ? C28 C29 C30 C31 -10.6(5) . . . . ? C28 C29 C30 C30 176.0(3) . . . 4_655 ? C29 C30 C31 C32 5.2(5) . . . . ? C30 C30 C31 C32 178.3(3) 4_655 . . . ? C28 C27 C32 C31 -12.3(5) . . . . ? C26 C27 C32 C31 171.9(3) . . . . ? C30 C31 C32 C27 6.6(6) . . . . ? C22 C21 N21 C25 -2.6(3) . . . . ? C22 C21 N21 Zn1 179.65(15) . . . . ? C24 C25 N21 C21 -0.1(3) . . . . ? C24 C25 N21 Zn1 177.74(17) . . . . ? O21 C26 N22 C23 -7.5(3) . . . . ? C27 C26 N22 C23 175.86(16) . . . . ? C22 C23 N22 C26 -164.12(18) . . . . ? C24 C23 N22 C26 14.9(3) . . . . ? O12 C11 O11 Zn1 -2.7(2) . . . . ? C12 C11 O11 Zn1 177.26(13) . . . . ? C11 O11 Zn1 O11 55.47(12) . . . 11 ? C11 O11 Zn1 N21 -176.47(12) . . . . ? C11 O11 Zn1 N21 -69.79(11) . . . 11 ? C21 N21 Zn1 O11 -20.25(17) . . . 11 ? C25 N21 Zn1 O11 162.07(14) . . . 11 ? C21 N21 Zn1 O11 -167.00(15) . . . . ? C25 N21 Zn1 O11 15.32(15) . . . . ? C21 N21 Zn1 N21 82.70(16) . . . 11 ? C25 N21 Zn1 N21 -94.98(16) . . . 11 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.595 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.103 # Attachment '3a.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 871164' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H23 N5 O6 Zn' _chemical_formula_weight 638.92 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(2)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/3' '-y, x-y, z+2/3' '-x, -y, z' '-x+y, -x, z+1/3' 'y, -x+y, z+2/3' '-y, -x, -z+2/3' 'x-y, -y, -z' 'x, x-y, -z+1/3' 'y, x, -z+2/3' '-x+y, y, -z' '-x, -x+y, -z+1/3' _cell_length_a 16.5755(6) _cell_length_b 16.5755(6) _cell_length_c 25.117(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5976.3(6) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6001 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 18.84 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8637 _exptl_absorpt_correction_T_max 0.8800 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30905 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0889 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3710 _reflns_number_gt 2117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0991P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 3710 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1037 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.41617(15) 0.67347(16) 0.06953(11) 0.0874(9) Uani 1 1 d . . . C12 C 0.46731(16) 0.71716(17) 0.12090(11) 0.0986(10) Uani 1 1 d . . . C13 C 0.4192(2) 0.70961(11) 0.1667 0.0837(11) Uani 1 2 d S . . H13 H 0.3544 0.6772 0.1667 0.100 Uiso 1 2 calc SR . . C14 C 0.56495(18) 0.7678(3) 0.11956(14) 0.1675(15) Uani 1 1 d . . . H14 H 0.5968 0.7753 0.0878 0.201 Uiso 1 1 calc R . . C15 C 0.6136(3) 0.80678(14) 0.1667 0.201(2) Uani 1 2 d S . . C21 C 0.08360(18) 0.44572(17) -0.01690(9) 0.0894(11) Uani 1 1 d . . . H21 H 0.0993 0.4604 -0.0525 0.107 Uiso 1 1 calc R . . C22 C -0.01135(15) 0.38353(15) -0.00370(9) 0.0765(9) Uani 1 1 d . . . H22 H -0.0564 0.3607 -0.0303 0.092 Uiso 1 1 calc R . . C23 C -0.03561(13) 0.35818(15) 0.04627(9) 0.0640(8) Uani 1 1 d . . . C24 C 0.03527(16) 0.3974(2) 0.08380(10) 0.1091(14) Uani 1 1 d . . . H24 H 0.0221 0.3816 0.1195 0.131 Uiso 1 1 calc R . . C25 C 0.12422(17) 0.45899(19) 0.06834(10) 0.0941(12) Uani 1 1 d . . . H25 H 0.1698 0.4857 0.0945 0.113 Uiso 1 1 calc R . . C26 C -0.16129(18) 0.2456(2) 0.10159(10) 0.1066(14) Uani 1 1 d . . . C27 C -0.26486(17) 0.17574(18) 0.10382(10) 0.0867(11) Uani 1 1 d . . . C28 C -0.3227(2) 0.1681(2) 0.06942(17) 0.1622(18) Uani 1 1 d . . . H28 H -0.3024 0.2083 0.0404 0.195 Uiso 1 1 calc R . . C29 C -0.4158(2) 0.1018(2) 0.07310(18) 0.1806(19) Uani 1 1 d . . . H29 H -0.4561 0.1037 0.0481 0.217 Uiso 1 1 calc R . . C30 C -0.45102(15) 0.03698(15) 0.10897(11) 0.0753(9) Uani 1 1 d . . . C31 C -0.3937(3) 0.0520(4) 0.14505(15) 0.247(3) Uani 1 1 d . . . H31 H -0.4156 0.0160 0.1757 0.297 Uiso 1 1 calc R . . C32 C -0.3006(2) 0.1178(4) 0.14307(15) 0.263(3) Uani 1 1 d . . . H32 H -0.2621 0.1208 0.1708 0.315 Uiso 1 1 calc R . . N11 N 0.7087(3) 0.85436(13) 0.1667 0.288(3) Uani 1 2 d S . . H11A H 0.7387 0.8784 0.1957 0.345 Uiso 0.50 1 calc PR . . H11B H 0.7387 0.8603 0.1376 0.345 Uiso 0.50 1 calc PR . . N21 N 0.14930(11) 0.48287(12) 0.01855(7) 0.0645(7) Uani 1 1 d . . . N22 N -0.12679(12) 0.29470(13) 0.05788(7) 0.0719(7) Uani 1 1 d . . . H22A H -0.1666 0.2859 0.0333 0.086 Uiso 1 1 calc R . . O11 O 0.33114(10) 0.62137(11) 0.07193(7) 0.0845(6) Uani 1 1 d . . . O12 O 0.46070(13) 0.69229(12) 0.02700(8) 0.1189(8) Uani 1 1 d . . . O21 O -0.11368(17) 0.2571(2) 0.14002(9) 0.2328(19) Uani 1 1 d . . . Zn1 Zn 0.286190(14) 0.57238(3) 0.0000 0.06516(11) Uani 1 2 d S . . 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 C11 0.0621(12) 0.0668(12) 0.131(2) -0.0245(12) 0.0264(13) 0.0309(9) C12 0.0518(11) 0.0787(14) 0.146(2) -0.0604(14) 0.0079(13) 0.0179(11) C13 0.0394(18) 0.0750(16) 0.125(2) -0.0508(18) 0.000 0.0197(9) C14 0.0538(15) 0.155(2) 0.226(3) -0.110(2) 0.0441(17) 0.0014(17) C15 0.035(2) 0.239(4) 0.261(4) -0.167(4) 0.000 0.0174(12) C21 0.0924(16) 0.0935(17) 0.0613(13) 0.0080(12) -0.0012(12) 0.0307(14) C22 0.0583(12) 0.0754(13) 0.0808(14) -0.0029(12) -0.0153(13) 0.0221(10) C23 0.0469(11) 0.0647(13) 0.0672(13) 0.0028(11) -0.0075(10) 0.0179(10) C24 0.0496(16) 0.130(2) 0.0698(15) 0.0205(16) 0.0032(12) -0.0131(16) C25 0.0528(14) 0.117(2) 0.0750(15) -0.0042(15) -0.0090(12) 0.0139(14) C26 0.0581(15) 0.126(2) 0.0829(17) 0.0124(16) -0.0183(14) 0.0065(15) C27 0.0526(15) 0.0729(17) 0.0786(15) 0.0053(13) -0.0170(12) -0.0106(13) C28 0.0598(19) 0.098(2) 0.252(4) 0.071(2) -0.030(2) -0.0180(17) C29 0.072(2) 0.141(3) 0.286(4) 0.102(3) -0.012(3) 0.0220(19) C30 0.0508(12) 0.0425(11) 0.1201(17) 0.0039(12) -0.0117(13) 0.0140(9) C31 0.081(3) 0.312(6) 0.146(3) 0.086(3) -0.012(2) -0.055(4) C32 0.080(2) 0.319(5) 0.143(3) 0.109(3) -0.034(2) -0.084(3) N11 0.043(2) 0.400(7) 0.301(5) -0.203(5) 0.000 0.0213(12) N21 0.0486(9) 0.0676(10) 0.0728(11) 0.0031(9) 0.0068(8) 0.0256(7) N22 0.0472(9) 0.0712(11) 0.0765(11) 0.0013(10) -0.0139(9) 0.0140(8) O11 0.0607(9) 0.0807(9) 0.0943(10) -0.0327(8) 0.0049(8) 0.0219(7) O12 0.1163(12) 0.0919(11) 0.1400(15) -0.0076(10) 0.0571(11) 0.0458(9) O21 0.0780(15) 0.316(3) 0.1041(13) 0.0911(16) -0.0259(12) -0.052(2) Zn1 0.05762(16) 0.0604(2) 0.0783(2) 0.000 0.01556(17) 0.03022(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O11 1.232(2) . ? C11 O12 1.246(3) . ? C11 C12 1.515(4) . ? C12 C13 1.369(3) . ? C12 C14 1.402(3) . ? C13 C12 1.369(3) 9_565 ? C13 H13 0.9300 . ? C14 C15 1.395(4) . ? C14 H14 0.9300 . ? C15 N11 1.366(5) . ? C15 C14 1.395(4) 9_565 ? C21 N21 1.299(3) . ? C21 C22 1.424(3) . ? C21 H21 0.9300 . ? C22 C23 1.321(3) . ? C22 H22 0.9300 . ? C23 N22 1.373(2) . ? C23 C24 1.388(3) . ? C24 C25 1.365(3) . ? C24 H24 0.9300 . ? C25 N21 1.315(3) . ? C25 H25 0.9300 . ? C26 O21 1.200(3) . ? C26 N22 1.315(3) . ? C26 C27 1.518(3) . ? C27 C28 1.249(5) . ? C27 C32 1.295(5) . ? C28 C29 1.379(4) . ? C28 H28 0.9300 . ? C29 C30 1.296(4) . ? C29 H29 0.9300 . ? C30 C31 1.244(5) . ? C30 C30 1.466(4) 4_455 ? C31 C32 1.375(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N11 H11A 0.8600 . ? N11 H11B 0.8600 . ? N21 Zn1 2.0495(15) . ? N22 H22A 0.8600 . ? O11 Zn1 1.9682(16) . ? Zn1 O11 1.9682(16) 11 ? Zn1 N21 2.0495(15) 11 ? 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 O11 C11 O12 123.0(2) . . ? O11 C11 C12 117.6(2) . . ? O12 C11 C12 119.4(2) . . ? C13 C12 C14 121.3(3) . . ? C13 C12 C11 120.7(2) . . ? C14 C12 C11 117.9(2) . . ? C12 C13 C12 119.4(3) 9_565 . ? C12 C13 H13 120.3 9_565 . ? C12 C13 H13 120.3 . . ? C15 C14 C12 118.9(3) . . ? C15 C14 H14 120.6 . . ? C12 C14 H14 120.6 . . ? N11 C15 C14 120.01(19) . 9_565 ? N11 C15 C14 120.01(19) . . ? C14 C15 C14 120.0(4) 9_565 . ? N21 C21 C22 123.0(2) . . ? N21 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 N22 119.26(19) . . ? C22 C23 C24 116.40(19) . . ? N22 C23 C24 124.3(2) . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? N21 C25 C24 123.8(2) . . ? N21 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? O21 C26 N22 121.7(2) . . ? O21 C26 C27 119.6(2) . . ? N22 C26 C27 118.6(2) . . ? C28 C27 C32 114.1(3) . . ? C28 C27 C26 124.8(3) . . ? C32 C27 C26 121.2(3) . . ? C27 C28 C29 122.1(4) . . ? C27 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? C30 C29 C28 124.6(4) . . ? C30 C29 H29 117.7 . . ? C28 C29 H29 117.7 . . ? C31 C30 C29 111.0(3) . . ? C31 C30 C30 125.6(2) . 4_455 ? C29 C30 C30 123.0(3) . 4_455 ? C30 C31 C32 125.0(4) . . ? C30 C31 H31 117.5 . . ? C32 C31 H31 117.5 . . ? C27 C32 C31 122.1(4) . . ? C27 C32 H32 118.9 . . ? C31 C32 H32 118.9 . . ? C15 N11 H11A 120.0 . . ? C15 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C21 N21 C25 116.45(18) . . ? C21 N21 Zn1 123.34(15) . . ? C25 N21 Zn1 120.20(14) . . ? C26 N22 C23 128.5(2) . . ? C26 N22 H22A 115.7 . . ? C23 N22 H22A 115.7 . . ? C11 O11 Zn1 107.97(17) . . ? O11 Zn1 O11 138.13(10) . 11 ? O11 Zn1 N21 107.71(8) . 11 ? O11 Zn1 N21 98.26(6) 11 11 ? O11 Zn1 N21 98.26(6) . . ? O11 Zn1 N21 107.71(8) 11 . ? N21 Zn1 N21 102.35(12) 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 O11 C11 C12 C13 -9.2(4) . . . . ? O12 C11 C12 C13 169.8(2) . . . . ? O11 C11 C12 C14 172.8(3) . . . . ? O12 C11 C12 C14 -8.2(5) . . . . ? C14 C12 C13 C12 -1.8(3) . . . 9_565 ? C11 C12 C13 C12 -179.7(3) . . . 9_565 ? C13 C12 C14 C15 3.5(5) . . . . ? C11 C12 C14 C15 -178.5(3) . . . . ? C12 C14 C15 N11 178.3(2) . . . . ? C12 C14 C15 C14 -1.7(2) . . . 9_565 ? N21 C21 C22 C23 -2.7(5) . . . . ? C21 C22 C23 N22 -176.9(3) . . . . ? C21 C22 C23 C24 1.8(4) . . . . ? C22 C23 C24 C25 0.5(5) . . . . ? N22 C23 C24 C25 179.1(3) . . . . ? C23 C24 C25 N21 -2.2(6) . . . . ? O21 C26 C27 C28 169.0(4) . . . . ? N22 C26 C27 C28 -8.5(6) . . . . ? O21 C26 C27 C32 -10.9(6) . . . . ? N22 C26 C27 C32 171.6(4) . . . . ? C32 C27 C28 C29 -1.4(7) . . . . ? C26 C27 C28 C29 178.6(4) . . . . ? C27 C28 C29 C30 -6.2(8) . . . . ? C28 C29 C30 C31 12.0(7) . . . . ? C28 C29 C30 C30 -174.7(4) . . . 4_455 ? C29 C30 C31 C32 -11.3(9) . . . . ? C30 C30 C31 C32 175.6(6) 4_455 . . . ? C28 C27 C32 C31 2.1(8) . . . . ? C26 C27 C32 C31 -177.9(5) . . . . ? C30 C31 C32 C27 5.0(11) . . . . ? C22 C21 N21 C25 1.1(4) . . . . ? C22 C21 N21 Zn1 180.0(2) . . . . ? C24 C25 N21 C21 1.3(5) . . . . ? C24 C25 N21 Zn1 -177.6(3) . . . . ? O21 C26 N22 C23 5.7(6) . . . . ? C27 C26 N22 C23 -176.9(3) . . . . ? C22 C23 N22 C26 163.6(3) . . . . ? C24 C23 N22 C26 -14.9(5) . . . . ? O12 C11 O11 Zn1 3.2(4) . . . . ? C12 C11 O11 Zn1 -177.9(2) . . . . ? C11 O11 Zn1 O11 -56.01(18) . . . 11 ? C11 O11 Zn1 N21 69.6(2) . . . 11 ? C11 O11 Zn1 N21 175.47(19) . . . . ? C21 N21 Zn1 O11 165.5(2) . . . . ? C25 N21 Zn1 O11 -15.6(2) . . . . ? C21 N21 Zn1 O11 18.8(2) . . . 11 ? C25 N21 Zn1 O11 -162.4(2) . . . 11 ? C21 N21 Zn1 N21 -84.2(2) . . . 11 ? C25 N21 Zn1 N21 94.7(2) . . . 11 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.396 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.077 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 871165' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H21 N5 O8 Zn' _chemical_formula_weight 668.91 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 Hexagonal _symmetry_space_group_name_H-M P6(4)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z' 'y, -x+y, z+1/3' 'x-y, x, z+2/3' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+1/3' '-x+y, y, -z' 'x, x-y, -z+2/3' _cell_length_a 16.5597(12) _cell_length_b 16.5597(12) _cell_length_c 25.787(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6124.0(11) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5369 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 21.84 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.088 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2052 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8551 _exptl_absorpt_correction_T_max 0.8816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30408 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.1068 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3773 _reflns_number_gt 2529 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.00178(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 3773 _refine_ls_number_parameters 212 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.173 _refine_ls_shift/su_mean 0.010 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 C11 C 0.73791(5) 0.32533(5) 0.06989(3) 0.0419(3) Uani 1 1 d . . . C12 C 0.74564(5) 0.28390(5) 0.12046(3) 0.0498(3) Uani 1 1 d . . . C13 C 0.70720(4) 0.29280(4) 0.1667 0.0403(3) Uani 1 2 d S . . H13 H 0.6748 0.3252 0.1667 0.048 Uiso 1 2 calc SR . . C14 C 0.79303(8) 0.23579(8) 0.12190(5) 0.1277(5) Uani 1 1 d . . . H14 H 0.8204 0.2275 0.0924 0.153 Uiso 1 1 calc R . . C15 C 0.79766(4) 0.20234(4) 0.1667 0.1972(6) Uani 1 2 d SD . . C21 C 0.64332(7) 0.56166(7) -0.01576(4) 0.0759(4) Uani 1 1 d . . . H21 H 0.6529 0.5543 -0.0506 0.091 Uiso 1 1 calc R . . C22 C 0.60747(7) 0.61972(6) -0.00238(4) 0.0791(4) Uani 1 1 d . . . H22A H 0.5907 0.6474 -0.0284 0.095 Uiso 1 1 calc R . . C23 C 0.59697(5) 0.63598(5) 0.04806(3) 0.0444(3) Uani 1 1 d . . . C24 C 0.61934(7) 0.58866(6) 0.08306(4) 0.0745(4) Uani 1 1 d . . . H24 H 0.6118 0.5949 0.1183 0.089 Uiso 1 1 calc R . . C25 C 0.65293(6) 0.53181(6) 0.06686(3) 0.0606(3) Uani 1 1 d . . . H25 H 0.6687 0.5019 0.0921 0.073 Uiso 1 1 calc R . . C26 C 0.56306(6) 0.73237(6) 0.10757(4) 0.0657(3) Uani 1 1 d . . . C27 C 0.53819(6) 0.80834(5) 0.10889(3) 0.0474(3) Uani 1 1 d . . . C28 C 0.55038(7) 0.85537(6) 0.15421(4) 0.0870(4) Uani 1 1 d . . . H28 H 0.5665 0.8353 0.1841 0.104 Uiso 1 1 calc R . . C29 C 0.53902(7) 0.93280(6) 0.15628(4) 0.0819(4) Uani 1 1 d . . . H29 H 0.5541 0.9678 0.1866 0.098 Uiso 1 1 calc R . . C30 C 0.50657(6) 0.95846(5) 0.11523(3) 0.0509(3) Uani 1 1 d . . . C31 C 0.48121(7) 0.90240(6) 0.07335(4) 0.0819(4) Uani 1 1 d . . . H31 H 0.4513 0.9136 0.0461 0.098 Uiso 1 1 calc R . . C32 C 0.49838(7) 0.82735(6) 0.06940(4) 0.0695(4) Uani 1 1 d . . . H32 H 0.4820 0.7913 0.0394 0.083 Uiso 1 1 calc R . . N11 N 0.84868(6) 0.15132(6) 0.1667 0.598(4) Uani 1 2 d SD . . N21 N 0.66377(4) 0.51752(4) 0.01932(2) 0.0423(2) Uani 1 1 d . . . N22 N 0.56790(5) 0.69885(5) 0.06025(3) 0.0557(3) Uani 1 1 d . . . H22 H 0.5506 0.7195 0.0344 0.067 Uiso 1 1 calc R . . O11 O 0.70734(4) 0.38100(4) 0.07119(2) 0.0531(2) Uani 1 1 d . . . O12 O 0.76432(4) 0.30400(4) 0.03057(2) 0.0631(3) Uani 1 1 d . . . O13 O 0.93479(9) 0.19876(11) 0.13803(8) 0.3474(11) Uani 1 1 d D . . O21 O 0.57917(6) 0.70321(5) 0.14618(3) 0.1531(3) Uani 1 1 d . . . Zn1 Zn 0.715394(5) 0.430788(10) 0.0000 0.03609(3) Uani 1 2 d S . . 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 C11 0.0415(4) 0.0532(4) 0.0265(4) 0.0038(3) 0.0045(3) 0.0202(3) C12 0.0650(4) 0.0626(4) 0.0384(5) 0.0103(4) 0.0149(3) 0.0444(3) C13 0.0486(3) 0.0486(3) 0.0342(5) 0.0078(5) 0.0078(5) 0.0322(3) C14 0.2205(6) 0.2113(6) 0.0632(7) 0.0559(5) 0.0682(5) 0.1920(3) C15 0.3664(5) 0.3664(5) 0.0792(12) 0.0748(17) 0.0748(17) 0.3487(5) C21 0.1376(5) 0.0959(5) 0.0375(5) 0.0012(4) -0.0020(4) 0.0908(3) C22 0.1447(5) 0.1080(4) 0.0363(5) -0.0026(5) -0.0105(5) 0.1019(3) C23 0.0646(4) 0.0494(4) 0.0314(5) -0.0016(3) -0.0068(4) 0.0375(3) C24 0.1455(6) 0.0920(4) 0.0315(5) -0.0071(4) -0.0077(4) 0.0935(3) C25 0.1089(5) 0.0775(4) 0.0282(5) -0.0069(4) -0.0122(4) 0.0712(3) C26 0.1132(5) 0.0826(4) 0.0395(5) -0.0100(4) -0.0138(4) 0.0776(3) C27 0.0733(4) 0.0527(3) 0.0355(5) -0.0032(3) -0.0068(4) 0.0459(3) C28 0.1717(6) 0.0957(4) 0.0489(6) -0.0088(4) -0.0194(5) 0.1084(3) C29 0.1478(6) 0.0895(5) 0.0453(6) -0.0172(4) -0.0079(5) 0.0869(3) C30 0.0771(4) 0.0503(4) 0.0417(5) -0.0038(4) -0.0076(4) 0.0442(3) C31 0.1404(6) 0.0823(4) 0.0640(7) -0.0141(5) -0.0282(5) 0.0864(3) C32 0.1194(5) 0.0656(4) 0.0532(5) -0.0122(4) -0.0269(5) 0.0686(3) N11 0.806(4) 0.806(4) 0.221(2) 0.295(2) 0.295(2) 0.432(5) N21 0.0492(3) 0.0493(3) 0.0349(4) 0.0009(3) -0.0016(3) 0.0294(2) N22 0.0903(4) 0.0665(3) 0.0353(4) -0.0057(3) -0.0141(3) 0.0578(2) O11 0.0709(3) 0.0661(3) 0.0348(3) 0.0128(2) 0.0058(3) 0.0438(2) O12 0.0811(3) 0.0757(3) 0.0323(3) 0.0041(3) 0.0202(3) 0.0392(2) O13 0.3928(10) 0.4112(10) 0.419(3) 0.0585(12) -0.0633(11) 0.3367(6) O21 0.3723(5) 0.2083(3) 0.0329(4) -0.0084(3) -0.0219(4) 0.2608(2) Zn1 0.03996(5) 0.04434(8) 0.02543(5) 0.000 0.00180(5) 0.02217(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O12 1.2242(11) . ? C11 O11 1.2547(13) . ? C11 C12 1.5084(12) . ? C12 C14 1.3700(19) . ? C12 C13 1.3931(10) . ? C13 C12 1.3931(10) 10_665 ? C13 H13 0.9300 . ? C14 C15 1.2991(14) . ? C14 H14 0.9300 . ? C15 C14 1.2992(14) 10_665 ? C15 N11 1.463(2) . ? C21 N21 1.3094(14) . ? C21 C22 1.4024(18) . ? C21 H21 0.9300 . ? C22 C23 1.3569(14) . ? C22 H22A 0.9300 . ? C23 C24 1.3624(15) . ? C23 N22 1.3842(14) . ? C24 C25 1.3762(17) . ? C24 H24 0.9300 . ? C25 N21 1.2781(11) . ? C25 H25 0.9300 . ? C26 O21 1.1936(13) . ? C26 N22 1.3593(12) . ? C26 C27 1.5072(16) . ? C27 C32 1.3336(15) . ? C27 C28 1.3623(14) . ? C28 C29 1.3870(17) . ? C28 H28 0.9300 . ? C29 C30 1.3485(15) . ? C29 H29 0.9300 . ? C30 C31 1.3471(13) . ? C30 C30 1.496(2) 4_675 ? C31 C32 1.4103(18) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N11 O13 1.4408(16) 10_665 ? N11 O13 1.4406(16) . ? N21 Zn1 2.0663(8) . ? N22 H22 0.8600 . ? O11 Zn1 1.9893(6) . ? Zn1 O11 1.9893(6) 11_655 ? Zn1 N21 2.0663(8) 11_655 ? 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 O12 C11 O11 124.59(8) . . ? O12 C11 C12 117.45(10) . . ? O11 C11 C12 117.93(8) . . ? C14 C12 C13 117.59(9) . . ? C14 C12 C11 119.44(9) . . ? C13 C12 C11 122.97(9) . . ? C12 C13 C12 121.67(12) 10_665 . ? C12 C13 H13 119.2 10_665 . ? C12 C13 H13 119.2 . . ? C15 C14 C12 116.42(11) . . ? C15 C14 H14 121.8 . . ? C12 C14 H14 121.8 . . ? C14 C15 C14 130.30(17) 10_665 . ? C14 C15 N11 114.85(8) 10_665 . ? C14 C15 N11 114.85(8) . . ? N21 C21 C22 121.94(9) . . ? N21 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 120.79(10) . . ? C23 C22 H22A 119.6 . . ? C21 C22 H22A 119.6 . . ? C22 C23 C24 114.98(10) . . ? C22 C23 N22 119.62(9) . . ? C24 C23 N22 125.38(8) . . ? C23 C24 C25 120.76(9) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? N21 C25 C24 124.06(10) . . ? N21 C25 H25 118.0 . . ? C24 C25 H25 118.0 . . ? O21 C26 N22 120.86(11) . . ? O21 C26 C27 121.90(9) . . ? N22 C26 C27 117.23(9) . . ? C32 C27 C28 118.00(11) . . ? C32 C27 C26 123.61(9) . . ? C28 C27 C26 118.19(9) . . ? C27 C28 C29 120.79(10) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 121.37(9) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C31 C30 C29 116.63(10) . . ? C31 C30 C30 119.67(8) . 4_675 ? C29 C30 C30 123.62(6) . 4_675 ? C30 C31 C32 122.31(11) . . ? C30 C31 H31 118.8 . . ? C32 C31 H31 118.8 . . ? C27 C32 C31 119.61(9) . . ? C27 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? O13 N11 O13 134.7(2) 10_665 . ? O13 N11 C15 112.64(10) 10_665 . ? O13 N11 C15 112.65(10) . . ? C25 N21 C21 117.37(10) . . ? C25 N21 Zn1 120.34(7) . . ? C21 N21 Zn1 122.26(7) . . ? C26 N22 C23 128.66(9) . . ? C26 N22 H22 115.7 . . ? C23 N22 H22 115.7 . . ? C11 O11 Zn1 108.17(5) . . ? O11 Zn1 O11 137.94(3) . 11_655 ? O11 Zn1 N21 95.75(3) . . ? O11 Zn1 N21 109.38(2) 11_655 . ? O11 Zn1 N21 109.38(2) . 11_655 ? O11 Zn1 N21 95.75(3) 11_655 11_655 ? N21 Zn1 N21 105.98(3) . 11_655 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.563 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.085 # Attachment '4a.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 871166' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H21 N5 O8 Zn' _chemical_formula_weight 668.91 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 Hexagonal _symmetry_space_group_name_H-M P6(2)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z' 'y, -x+y, z+2/3' 'x-y, x, z+1/3' 'y, x, -z+2/3' 'x-y, -y, -z' '-x, -x+y, -z+1/3' '-y, -x, -z+2/3' '-x+y, y, -z' 'x, x-y, -z+1/3' _cell_length_a 16.5094(8) _cell_length_b 16.5094(8) _cell_length_c 25.701(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6066.5(7) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3956 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 21.92 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2052 _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 0.9084 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30337 _diffrn_reflns_av_R_equivalents 0.0854 _diffrn_reflns_av_sigmaI/netI 0.1059 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3737 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 3737 _refine_ls_number_parameters 211 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.002 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 C11 C 0.26301(18) 0.5884(2) 0.90346(10) 0.0431(9) Uani 1 1 d . . . C12 C 0.2546(2) 0.53788(19) 0.95360(10) 0.0506(10) Uani 1 1 d . . . C13 C 0.29243(14) 0.5849(3) 1.0000 0.0430(10) Uani 1 2 d S . . H13A H 0.3250 0.6499 1.0000 0.052 Uiso 1 2 calc SR . . C14 C 0.2068(5) 0.4424(3) 0.95454(16) 0.154(3) Uani 1 1 d . . . H14A H 0.1799 0.4084 0.9244 0.185 Uiso 1 1 calc R . . C15 C 0.19908(18) 0.3982(4) 1.0000 0.239(6) Uani 1 2 d S . . C21 C 0.3498(3) 0.8802(2) 0.90116(11) 0.0647(13) Uani 1 1 d . . . H21A H 0.3373 0.8352 0.9265 0.078 Uiso 1 1 calc R . . C22 C 0.3813(3) 0.9695(2) 0.91719(12) 0.0719(14) Uani 1 1 d . . . H22A H 0.3879 0.9836 0.9525 0.086 Uiso 1 1 calc R . . C23 C 0.4030(2) 1.03845(19) 0.88146(11) 0.0437(9) Uani 1 1 d . . . C24 C 0.3940(3) 1.0117(2) 0.83085(13) 0.0791(13) Uani 1 1 d . . . H24A H 0.4129 1.0566 0.8048 0.095 Uiso 1 1 calc R . . C25 C 0.3575(3) 0.9192(2) 0.81764(12) 0.0776(13) Uani 1 1 d . . . H25A H 0.3475 0.9028 0.7826 0.093 Uiso 1 1 calc R . . C26 C 0.4367(3) 1.1699(2) 0.94034(12) 0.0665(13) Uani 1 1 d . . . C27 C 0.4616(2) 1.26946(19) 0.94223(12) 0.0475(10) Uani 1 1 d . . . C28 C 0.4493(3) 1.3047(2) 0.98740(13) 0.0876(15) Uani 1 1 d . . . H28A H 0.4326 1.2682 1.0173 0.105 Uiso 1 1 calc R . . C29 C 0.4612(3) 1.3938(2) 0.98985(13) 0.0805(13) Uani 1 1 d . . . H29A H 0.4466 1.4137 1.0205 0.097 Uiso 1 1 calc R . . C30 C 0.4935(2) 1.45225(19) 0.94882(11) 0.0532(10) Uani 1 1 d . . . C31 C 0.5179(3) 1.4211(2) 0.90636(15) 0.0901(15) Uani 1 1 d . . . H31A H 0.5470 1.4621 0.8788 0.108 Uiso 1 1 calc R . . C32 C 0.5010(3) 1.3280(2) 0.90217(13) 0.0756(12) Uani 1 1 d . . . H32A H 0.5171 1.3082 0.8720 0.091 Uiso 1 1 calc R . . N11 N 0.1491(4) 0.2981(8) 1.0000 0.291(5) Uani 1 2 d SU . . N21 N 0.33602(16) 0.85317(15) 0.85220(8) 0.0449(8) Uani 1 1 d . . . N22 N 0.43195(19) 1.13076(17) 0.89343(9) 0.0582(9) Uani 1 1 d . . . H22C H 0.4493 1.1685 0.8674 0.070 Uiso 1 1 calc R . . O11 O 0.29275(14) 0.67329(13) 0.90457(7) 0.0532(7) Uani 1 1 d . . . O12 O 0.23653(15) 0.54022(16) 0.86340(8) 0.0651(8) Uani 1 1 d . . . O13 O 0.1644(7) 0.2548(6) 1.0402(4) 0.343(4) Uani 1 1 d U . . O21 O 0.4207(3) 1.12403(18) 0.97957(9) 0.1528(16) Uani 1 1 d . . . Zn1 Zn 0.284658(17) 0.715342(17) 0.8333 0.03779(11) Uani 1 2 d S . . 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 C11 0.0352(13) 0.0624(16) 0.0279(13) -0.0035(12) -0.0063(11) 0.0216(11) C12 0.0657(18) 0.0375(15) 0.0376(15) -0.0041(12) -0.0133(14) 0.0175(13) C13 0.0533(18) 0.035(2) 0.0346(18) 0.000 -0.0051(19) 0.0174(12) C14 0.271(6) 0.053(2) 0.062(2) -0.011(2) -0.072(3) 0.023(3) C15 0.468(13) 0.011(3) 0.085(4) 0.000 -0.124(6) 0.0055(13) C21 0.116(3) 0.0449(16) 0.0317(15) 0.0033(12) 0.0103(17) 0.0393(16) C22 0.129(3) 0.0502(18) 0.0340(16) -0.0023(13) 0.0026(18) 0.0426(17) C23 0.0568(15) 0.0368(14) 0.0369(15) 0.0050(12) 0.0067(13) 0.0229(11) C24 0.143(3) 0.0535(16) 0.0402(16) 0.0097(16) 0.010(2) 0.0486(16) C25 0.145(3) 0.0574(17) 0.0362(16) 0.0027(14) 0.0038(18) 0.0549(17) C26 0.105(2) 0.0484(17) 0.0389(17) 0.0052(14) 0.0153(17) 0.0330(17) C27 0.0660(16) 0.0362(14) 0.0445(17) 0.0019(12) 0.0052(14) 0.0287(11) C28 0.170(3) 0.0467(17) 0.049(2) 0.0081(15) 0.014(2) 0.0560(18) C29 0.143(3) 0.0650(18) 0.0463(19) -0.0048(15) 0.0137(19) 0.0613(16) C30 0.0801(17) 0.0422(14) 0.0441(16) 0.0024(13) 0.0089(15) 0.0357(12) C31 0.152(3) 0.0559(19) 0.069(2) 0.0124(18) 0.037(2) 0.0565(18) C32 0.140(2) 0.0500(15) 0.0525(18) 0.0169(15) 0.0351(19) 0.0590(15) N11 0.402(10) 0.205(8) 0.201(7) 0.000 -0.090(8) 0.103(4) N21 0.0576(14) 0.0406(12) 0.0354(12) 0.0009(10) 0.0020(11) 0.0238(10) N22 0.0907(16) 0.0420(13) 0.0377(13) 0.0101(11) 0.0177(13) 0.0299(12) O11 0.0694(11) 0.0490(10) 0.0354(10) 0.0061(8) -0.0040(9) 0.0253(8) O12 0.0798(13) 0.0808(14) 0.0352(10) -0.0144(10) -0.0160(10) 0.0404(10) O13 0.393(6) 0.288(5) 0.330(6) 0.002(4) -0.045(5) 0.157(4) O21 0.360(4) 0.0588(13) 0.0387(13) 0.0072(11) 0.013(2) 0.1039(18) Zn1 0.04129(11) 0.04129(11) 0.02811(18) -0.00165(19) -0.00165(19) 0.01864(16) _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 C11 O12 1.239(3) . ? C11 O11 1.233(4) . ? C11 C12 1.503(4) . ? C12 C14 1.366(5) . ? C12 C13 1.389(3) . ? C13 C12 1.389(3) 11_557 ? C13 H13A 0.9300 . ? C14 C15 1.350(5) . ? C14 H14A 0.9300 . ? C15 C14 1.350(5) 11_557 ? C15 N11 1.430(13) . ? C21 N21 1.316(4) . ? C21 C22 1.359(4) . ? C21 H21A 0.9300 . ? C22 C23 1.364(4) . ? C22 H22A 0.9300 . ? C23 C24 1.358(4) . ? C23 N22 1.385(4) . ? C24 C25 1.375(5) . ? C24 H24A 0.9300 . ? C25 N21 1.310(4) . ? C25 H25A 0.9300 . ? C26 O21 1.208(4) . ? C26 N22 1.351(4) . ? C26 C27 1.482(5) . ? C27 C32 1.337(4) . ? C27 C28 1.358(5) . ? C28 C29 1.386(5) . ? C28 H28A 0.9300 . ? C29 C30 1.346(4) . ? C29 H29A 0.9300 . ? C30 C31 1.352(5) . ? C30 C30 1.481(6) 4_685 ? C31 C32 1.421(6) . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? N11 O13 1.350(11) . ? N11 O13 1.350(11) 11_557 ? N21 Zn1 2.050(2) . ? N22 H22C 0.8600 . ? O11 Zn1 1.9860(19) . ? Zn1 O11 1.9860(19) 10_666 ? Zn1 N21 2.050(2) 10_666 ? 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 O12 C11 O11 124.1(3) . . ? O12 C11 C12 116.9(3) . . ? O11 C11 C12 119.0(2) . . ? C14 C12 C13 117.9(3) . . ? C14 C12 C11 119.7(3) . . ? C13 C12 C11 122.4(3) . . ? C12 C13 C12 122.2(4) . 11_557 ? C12 C13 H13A 118.9 . . ? C12 C13 H13A 118.9 11_557 . ? C15 C14 C12 118.9(4) . . ? C15 C14 H14A 120.5 . . ? C12 C14 H14A 120.5 . . ? C14 C15 C14 124.1(5) 11_557 . ? C14 C15 N11 117.9(3) 11_557 . ? C14 C15 N11 117.9(3) . . ? N21 C21 C22 124.4(3) . . ? N21 C21 H21A 117.8 . . ? C22 C21 H21A 117.8 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22A 120.0 . . ? C23 C22 H22A 120.0 . . ? C22 C23 C24 115.7(3) . . ? C22 C23 N22 124.8(3) . . ? C24 C23 N22 119.5(3) . . ? C23 C24 C25 120.9(3) . . ? C23 C24 H24A 119.5 . . ? C25 C24 H24A 119.5 . . ? N21 C25 C24 122.9(3) . . ? N21 C25 H25A 118.6 . . ? C24 C25 H25A 118.6 . . ? O21 C26 N22 120.2(3) . . ? O21 C26 C27 121.3(3) . . ? N22 C26 C27 118.5(3) . . ? C32 C27 C28 118.1(3) . . ? C32 C27 C26 122.8(3) . . ? C28 C27 C26 119.0(3) . . ? C27 C28 C29 121.4(3) . . ? C27 C28 H28A 119.3 . . ? C29 C28 H28A 119.3 . . ? C30 C29 C28 121.4(3) . . ? C30 C29 H29A 119.3 . . ? C28 C29 H29A 119.3 . . ? C29 C30 C31 116.5(3) . . ? C29 C30 C30 123.9(3) . 4_685 ? C31 C30 C30 119.6(2) . 4_685 ? C30 C31 C32 122.6(3) . . ? C30 C31 H31A 118.7 . . ? C32 C31 H31A 118.7 . . ? C27 C32 C31 119.0(3) . . ? C27 C32 H32A 120.5 . . ? C31 C32 H32A 120.5 . . ? O13 N11 O13 125.4(12) . 11_557 ? O13 N11 C15 117.3(6) . . ? O13 N11 C15 117.3(6) 11_557 . ? C21 N21 C25 115.9(3) . . ? C21 N21 Zn1 120.5(2) . . ? C25 N21 Zn1 123.6(2) . . ? C26 N22 C23 129.1(3) . . ? C26 N22 H22C 115.5 . . ? C23 N22 H22C 115.5 . . ? C11 O11 Zn1 108.56(17) . . ? O11 Zn1 O11 137.68(14) 10_666 . ? O11 Zn1 N21 96.15(9) 10_666 10_666 ? O11 Zn1 N21 109.16(8) . 10_666 ? O11 Zn1 N21 109.16(8) 10_666 . ? O11 Zn1 N21 96.15(9) . . ? N21 Zn1 N21 105.82(15) 10_666 . ? 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 O12 C11 C12 C14 -9.6(6) . . . . ? O11 C11 C12 C14 168.3(5) . . . . ? O12 C11 C12 C13 171.8(3) . . . . ? O11 C11 C12 C13 -10.3(5) . . . . ? C14 C12 C13 C12 0.3(4) . . . 11_557 ? C11 C12 C13 C12 179.0(4) . . . 11_557 ? C13 C12 C14 C15 -0.6(8) . . . . ? C11 C12 C14 C15 -179.3(4) . . . . ? C12 C14 C15 C14 0.3(4) . . . 11_557 ? C12 C14 C15 N11 -179.7(4) . . . . ? N21 C21 C22 C23 -1.7(7) . . . . ? C21 C22 C23 C24 -2.1(6) . . . . ? C21 C22 C23 N22 177.3(4) . . . . ? C22 C23 C24 C25 5.4(6) . . . . ? N22 C23 C24 C25 -174.1(4) . . . . ? C23 C24 C25 N21 -5.3(7) . . . . ? O21 C26 C27 C32 163.6(4) . . . . ? N22 C26 C27 C32 -16.7(6) . . . . ? O21 C26 C27 C28 -12.3(6) . . . . ? N22 C26 C27 C28 167.5(4) . . . . ? C32 C27 C28 C29 11.4(6) . . . . ? C26 C27 C28 C29 -172.6(4) . . . . ? C27 C28 C29 C30 -6.0(7) . . . . ? C28 C29 C30 C31 -3.2(6) . . . . ? C28 C29 C30 C30 179.2(4) . . . 4_685 ? C29 C30 C31 C32 7.1(6) . . . . ? C30 C30 C31 C32 -175.2(4) 4_685 . . . ? C28 C27 C32 C31 -7.4(6) . . . . ? C26 C27 C32 C31 176.7(4) . . . . ? C30 C31 C32 C27 -1.8(6) . . . . ? C14 C15 N11 O13 -19.1(7) 11_557 . . . ? C14 C15 N11 O13 160.9(7) . . . . ? C14 C15 N11 O13 160.9(7) 11_557 . . 11_557 ? C14 C15 N11 O13 -19.1(7) . . . 11_557 ? C22 C21 N21 C25 2.2(6) . . . . ? C22 C21 N21 Zn1 -178.2(3) . . . . ? C24 C25 N21 C21 1.3(6) . . . . ? C24 C25 N21 Zn1 -178.3(3) . . . . ? O21 C26 N22 C23 5.7(7) . . . . ? C27 C26 N22 C23 -174.1(3) . . . . ? C22 C23 N22 C26 -6.5(6) . . . . ? C24 C23 N22 C26 172.9(4) . . . . ? O12 C11 O11 Zn1 2.6(4) . . . . ? C12 C11 O11 Zn1 -175.2(2) . . . . ? C11 O11 Zn1 O11 -53.55(19) . . . 10_666 ? C11 O11 Zn1 N21 69.8(2) . . . 10_666 ? C11 O11 Zn1 N21 179.0(2) . . . . ? C21 N21 Zn1 O11 -153.8(3) . . . 10_666 ? C25 N21 Zn1 O11 25.8(3) . . . 10_666 ? C21 N21 Zn1 O11 -8.2(3) . . . . ? C25 N21 Zn1 O11 171.4(3) . . . . ? C21 N21 Zn1 N21 103.7(3) . . . 10_666 ? C25 N21 Zn1 N21 -76.7(3) . . . 10_666 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.609 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.084 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 871167' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H21 N4 O8 Zn' _chemical_formula_weight 666.91 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(4)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+2/3' '-y, x-y, z+1/3' '-x, -y, z' '-x+y, -x, z+2/3' 'y, -x+y, z+1/3' '-y, -x, -z+1/3' 'x-y, -y, -z' 'x, x-y, -z+2/3' 'y, x, -z+1/3' '-x+y, y, -z' '-x, -x+y, -z+2/3' _cell_length_a 16.5097(2) _cell_length_b 16.5097(2) _cell_length_c 25.4661(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6011.34(16) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9315 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 22.13 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2046 _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8528 _exptl_absorpt_correction_T_max 0.8581 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29998 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3547 _reflns_number_gt 2874 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1594P)^2^+0.0159P] 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 SHELXL _refine_ls_extinction_coef 0.0084(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(3) _refine_ls_number_reflns 3547 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2301 _refine_ls_wR_factor_gt 0.2169 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 C11 C 0.7399(5) 0.4162(5) 0.0967(2) 0.0597(16) Uani 1 1 d . . . C13 C 0.7096(3) 0.4192(6) 0.0000 0.057(2) Uani 1 2 d S . . H13 H 0.6771 0.3541 0.0000 0.069 Uiso 1 2 calc SR . . C30 C 0.5093(5) -0.4508(4) 0.0552(2) 0.0628(16) Uani 1 1 d . . . C25 C 0.6029(5) -0.0354(4) 0.1204(2) 0.0556(16) Uani 1 1 d . . . C27 C 0.5487(6) -0.2672(4) 0.0608(3) 0.0658(18) Uani 1 1 d . . . C12 C 0.7466(5) 0.4665(4) 0.0464(3) 0.0666(19) Uani 1 1 d . . . C23 C 0.6082(6) -0.0095(5) 0.1706(2) 0.077(2) Uani 1 1 d . . . H23 H 0.5921 -0.0538 0.1970 0.092 Uiso 1 1 calc R . . C24 C 0.6374(6) 0.0827(5) 0.1838(2) 0.083(2) Uani 1 1 d . . . H24 H 0.6395 0.0985 0.2190 0.100 Uiso 1 1 calc R . . C26 C 0.5738(8) -0.1665(5) 0.0613(3) 0.094(3) Uani 1 1 d . . . C32 C 0.5063(8) -0.3270(6) 0.1005(4) 0.100(3) Uani 1 1 d . . . H32 H 0.4929 -0.3074 0.1319 0.119 Uiso 1 1 calc R . . C21 C 0.6548(6) 0.1226(5) 0.0985(2) 0.076(2) Uani 1 1 d . . . H21 H 0.6678 0.1672 0.0726 0.091 Uiso 1 1 calc R . . C22 C 0.6293(7) 0.0345(5) 0.0829(3) 0.090(3) Uani 1 1 d . . . H22 H 0.6296 0.0211 0.0475 0.108 Uiso 1 1 calc R . . C31 C 0.4837(9) -0.4181(6) 0.0930(4) 0.122(4) Uani 1 1 d . . . H31 H 0.4454 -0.4608 0.1183 0.147 Uiso 1 1 calc R . . C28 C 0.5606(13) -0.3023(8) 0.0156(4) 0.162(7) Uani 1 1 d . . . H28 H 0.5838 -0.2648 -0.0141 0.194 Uiso 1 1 calc R . . C14 C 0.7904(10) 0.5625(5) 0.0470(4) 0.143(6) Uani 1 1 d . . . H14 H 0.8097 0.5947 0.0787 0.171 Uiso 1 1 calc R . . C29 C 0.5373(14) -0.3963(7) 0.0143(4) 0.171(8) Uani 1 1 d . . . H29 H 0.5420 -0.4212 -0.0176 0.206 Uiso 1 1 calc R . . C15 C 0.8058(4) 0.6116(8) 0.0000 0.213(15) Uani 1 2 d S . . C16 C 0.8597(6) 0.7194(11) 0.0000 0.35(3) Uani 1 2 d S . . N21 N 0.6622(3) 0.1489(3) 0.14774(18) 0.0537(12) Uani 1 1 d . . . N22 N 0.5727(5) -0.1284(3) 0.10820(19) 0.0659(15) Uani 1 1 d . . . H22A H 0.5502 -0.1670 0.1340 0.079 Uiso 1 1 calc R . . O11 O 0.7068(3) 0.3297(3) 0.09516(16) 0.0636(12) Uani 1 1 d . . . O12 O 0.7662(4) 0.4627(4) 0.13858(19) 0.0831(15) Uani 1 1 d . . . O21 O 0.5991(10) -0.1181(5) 0.0221(2) 0.221(7) Uani 1 1 d . . . O13 O 0.9087(16) 0.7605(7) 0.0366(4) 0.360(14) Uani 1 1 d . . . Zn1 Zn 0.71280(3) 0.28720(3) 0.1667 0.0471(3) Uani 1 2 d S . . 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 C11 0.056(4) 0.064(4) 0.056(3) -0.016(3) -0.023(3) 0.028(3) C13 0.061(4) 0.038(4) 0.066(5) 0.000 -0.024(4) 0.019(2) C30 0.071(4) 0.052(4) 0.071(4) 0.002(3) 0.004(3) 0.035(3) C25 0.073(4) 0.042(3) 0.056(3) 0.005(2) 0.012(3) 0.031(3) C27 0.094(5) 0.050(4) 0.057(4) 0.000(3) 0.008(3) 0.038(4) C12 0.076(5) 0.040(3) 0.074(4) -0.007(3) -0.032(4) 0.021(3) C23 0.119(6) 0.054(4) 0.055(3) 0.010(3) 0.005(4) 0.040(4) C24 0.127(7) 0.056(4) 0.047(3) 0.004(3) 0.004(4) 0.033(4) C26 0.168(9) 0.053(4) 0.063(4) 0.009(4) 0.031(5) 0.058(5) C32 0.158(9) 0.063(5) 0.092(5) 0.014(4) 0.040(6) 0.065(6) C21 0.125(7) 0.050(4) 0.040(3) 0.004(3) 0.008(4) 0.036(4) C22 0.161(8) 0.044(4) 0.050(3) 0.004(3) 0.023(4) 0.040(4) C31 0.208(13) 0.072(6) 0.100(6) 0.024(5) 0.055(7) 0.079(8) C28 0.33(2) 0.090(7) 0.089(6) 0.006(5) 0.034(9) 0.122(11) C14 0.212(13) 0.042(4) 0.133(8) -0.022(5) -0.110(9) 0.033(6) C29 0.38(2) 0.077(6) 0.087(6) -0.002(5) 0.019(9) 0.134(11) C15 0.36(3) 0.037(6) 0.136(13) 0.000 -0.134(18) 0.018(3) C16 0.62(7) 0.042(8) 0.18(2) 0.000 -0.17(4) 0.021(4) N21 0.053(3) 0.050(3) 0.054(3) 0.001(2) 0.000(2) 0.023(2) N22 0.091(4) 0.043(3) 0.061(3) 0.014(2) 0.018(3) 0.031(3) O11 0.079(3) 0.060(3) 0.051(2) 0.0026(19) -0.013(2) 0.034(3) O12 0.090(4) 0.095(4) 0.070(3) -0.026(3) -0.030(3) 0.051(3) O21 0.53(2) 0.086(5) 0.064(3) 0.031(3) 0.082(7) 0.170(9) O13 0.61(3) 0.076(6) 0.200(13) -0.030(6) -0.136(18) 0.026(13) Zn1 0.0468(4) 0.0468(4) 0.0439(5) -0.0043(3) -0.0043(3) 0.0205(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 O11 1.248(8) . ? C11 O12 1.258(8) . ? C11 C12 1.501(9) . ? C13 C12 1.379(7) . ? C13 C12 1.379(7) 11_655 ? C13 H13 0.9300 . ? C30 C31 1.277(11) . ? C30 C29 1.301(11) . ? C30 C30 1.493(13) 4_645 ? C25 C23 1.338(9) . ? C25 C22 1.389(8) . ? C25 N22 1.391(7) . ? C27 C32 1.340(10) . ? C27 C28 1.346(12) . ? C27 C26 1.498(9) . ? C12 C14 1.374(10) . ? C23 C24 1.388(11) . ? C23 H23 0.9300 . ? C24 N21 1.325(8) . ? C24 H24 0.9300 . ? C26 O21 1.215(9) . ? C26 N22 1.355(9) . ? C32 C31 1.370(12) . ? C32 H32 0.9300 . ? C21 N21 1.313(8) . ? C21 C22 1.354(10) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C31 H31 0.9300 . ? C28 C29 1.401(13) . ? C28 H28 0.9300 . ? C14 C15 1.396(10) . ? C14 H14 0.9300 . ? C29 H29 0.9300 . ? C15 C14 1.396(10) 11_655 ? C15 C16 1.541(19) . ? C16 O13 1.197(13) . ? C16 O13 1.197(13) 11_655 ? N21 Zn1 2.058(5) . ? N22 H22A 0.8600 . ? O11 Zn1 1.971(4) . ? Zn1 O11 1.971(4) 7_665 ? Zn1 N21 2.058(5) 7_665 ? 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 O11 C11 O12 123.0(7) . . ? O11 C11 C12 118.5(5) . . ? O12 C11 C12 118.6(6) . . ? C12 C13 C12 121.2(8) . 11_655 ? C12 C13 H13 119.4 . . ? C12 C13 H13 119.4 11_655 . ? C31 C30 C29 112.9(7) . . ? C31 C30 C30 121.9(6) . 4_645 ? C29 C30 C30 124.1(5) . 4_645 ? C23 C25 C22 116.5(6) . . ? C23 C25 N22 119.8(5) . . ? C22 C25 N22 123.7(5) . . ? C32 C27 C28 117.5(7) . . ? C32 C27 C26 124.4(7) . . ? C28 C27 C26 117.8(7) . . ? C14 C12 C13 119.5(7) . . ? C14 C12 C11 118.6(6) . . ? C13 C12 C11 121.8(6) . . ? C25 C23 C24 120.9(6) . . ? C25 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? N21 C24 C23 122.1(6) . . ? N21 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? O21 C26 N22 119.9(6) . . ? O21 C26 C27 122.4(7) . . ? N22 C26 C27 117.5(6) . . ? C27 C32 C31 117.4(8) . . ? C27 C32 H32 121.3 . . ? C31 C32 H32 121.3 . . ? N21 C21 C22 124.2(6) . . ? N21 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? C21 C22 C25 119.5(6) . . ? C21 C22 H22 120.3 . . ? C25 C22 H22 120.3 . . ? C30 C31 C32 127.1(9) . . ? C30 C31 H31 116.4 . . ? C32 C31 H31 116.4 . . ? C27 C28 C29 118.7(9) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? C12 C14 C15 119.8(8) . . ? C12 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C30 C29 C28 123.6(9) . . ? C30 C29 H29 118.2 . . ? C28 C29 H29 118.2 . . ? C14 C15 C14 119.6(10) 11_655 . ? C14 C15 C16 120.2(5) 11_655 . ? C14 C15 C16 120.2(5) . . ? O13 C16 O13 121.2(17) . 11_655 ? O13 C16 C15 119.4(8) . . ? O13 C16 C15 119.4(9) 11_655 . ? C21 N21 C24 116.7(6) . . ? C21 N21 Zn1 120.7(4) . . ? C24 N21 Zn1 122.6(4) . . ? C26 N22 C25 128.9(5) . . ? C26 N22 H22A 115.5 . . ? C25 N22 H22A 115.5 . . ? C11 O11 Zn1 107.9(4) . . ? O11 Zn1 O11 138.9(3) 7_665 . ? O11 Zn1 N21 96.53(18) 7_665 7_665 ? O11 Zn1 N21 108.34(19) . 7_665 ? O11 Zn1 N21 108.34(19) 7_665 . ? O11 Zn1 N21 96.53(18) . . ? N21 Zn1 N21 104.9(3) 7_665 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 C13 C12 C14 3.4(9) 11_655 . . . ? C12 C13 C12 C11 -177.1(8) 11_655 . . . ? O11 C11 C12 C14 -174.4(10) . . . . ? O12 C11 C12 C14 7.0(13) . . . . ? O11 C11 C12 C13 6.1(10) . . . . ? O12 C11 C12 C13 -172.5(6) . . . . ? C22 C25 C23 C24 1.0(12) . . . . ? N22 C25 C23 C24 -179.5(8) . . . . ? C25 C23 C24 N21 -0.9(13) . . . . ? C32 C27 C26 O21 -168.7(13) . . . . ? C28 C27 C26 O21 4(2) . . . . ? C32 C27 C26 N22 15.0(16) . . . . ? C28 C27 C26 N22 -172.1(12) . . . . ? C28 C27 C32 C31 3.8(17) . . . . ? C26 C27 C32 C31 176.8(11) . . . . ? N21 C21 C22 C25 4.6(16) . . . . ? C23 C25 C22 C21 -2.7(14) . . . . ? N22 C25 C22 C21 177.8(9) . . . . ? C29 C30 C31 C32 -20(2) . . . . ? C30 C30 C31 C32 171.5(11) 4_645 . . . ? C27 C32 C31 C30 10(2) . . . . ? C32 C27 C28 C29 -6(2) . . . . ? C26 C27 C28 C29 -179.8(15) . . . . ? C13 C12 C14 C15 -6.8(17) . . . . ? C11 C12 C14 C15 173.7(9) . . . . ? C31 C30 C29 C28 16(2) . . . . ? C30 C30 C29 C28 -175.6(15) 4_645 . . . ? C27 C28 C29 C30 -4(3) . . . . ? C12 C14 C15 C14 3.4(9) . . . 11_655 ? C12 C14 C15 C16 -176.6(9) . . . . ? C14 C15 C16 O13 -160.3(15) 11_655 . . . ? C14 C15 C16 O13 19.7(15) . . . . ? C14 C15 C16 O13 19.7(15) 11_655 . . 11_655 ? C14 C15 C16 O13 -160.3(15) . . . 11_655 ? C22 C21 N21 C24 -4.4(13) . . . . ? C22 C21 N21 Zn1 174.5(8) . . . . ? C23 C24 N21 C21 2.4(12) . . . . ? C23 C24 N21 Zn1 -176.4(6) . . . . ? O21 C26 N22 C25 -4.4(18) . . . . ? C27 C26 N22 C25 171.9(8) . . . . ? C23 C25 N22 C26 -170.6(9) . . . . ? C22 C25 N22 C26 9.0(14) . . . . ? O12 C11 O11 Zn1 -3.6(8) . . . . ? C12 C11 O11 Zn1 177.8(5) . . . . ? C11 O11 Zn1 O11 55.6(4) . . . 7_665 ? C11 O11 Zn1 N21 -68.6(5) . . . 7_665 ? C11 O11 Zn1 N21 -176.6(5) . . . . ? C21 N21 Zn1 O11 158.9(6) . . . 7_665 ? C24 N21 Zn1 O11 -22.3(6) . . . 7_665 ? C21 N21 Zn1 O11 12.1(6) . . . . ? C24 N21 Zn1 O11 -169.1(6) . . . . ? C21 N21 Zn1 N21 -98.9(6) . . . 7_665 ? C24 N21 Zn1 N21 79.9(6) . . . 7_665 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.714 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.175 # Attachment '5a.cif' data_5a _database_code_depnum_ccdc_archive 'CCDC 871168' #TrackingRef '5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H21 N4 O8 Zn' _chemical_formula_weight 666.91 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' O O 0.0106 0.0060 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(2)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/3' '-y, x-y, z+2/3' '-x, -y, z' '-x+y, -x, z+1/3' 'y, -x+y, z+2/3' '-y, -x, -z+2/3' 'x-y, -y, -z' 'x, x-y, -z+1/3' 'y, x, -z+2/3' '-x+y, y, -z' '-x, -x+y, -z+1/3' _cell_length_a 16.5028(4) _cell_length_b 16.5028(4) _cell_length_c 25.4515(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6002.9(4) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5203 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 19.21 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2046 _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8579 _exptl_absorpt_correction_T_max 0.9076 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29473 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3723 _reflns_number_gt 2704 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1234P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 3723 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C11 C 0.67737(18) 0.41810(19) 0.09696(11) 0.0625(8) Uani 1 1 d . . . C12 C 0.7197(2) 0.46821(19) 0.04587(12) 0.0738(10) Uani 1 1 d . . . C13 C 0.71056(14) 0.4211(3) 0.0000 0.0611(10) Uani 1 2 d S . . H13 H 0.6780 0.3560 0.0000 0.073 Uiso 1 2 calc SR . . C14 C 0.7710(4) 0.5653(2) 0.04500(16) 0.143(2) Uani 1 1 d . . . H14 H 0.7810 0.5982 0.0763 0.172 Uiso 1 1 calc R . . C15 C 0.8065(2) 0.6130(4) 0.0000 0.220(4) Uani 1 2 d S . . C16 C 0.8571(3) 0.7142(6) 0.0000 0.419(11) Uani 1 2 d S . . C21 C 0.4673(2) 0.1242(2) 0.09875(11) 0.0768(13) Uani 1 1 d . . . H21 H 0.4958 0.1697 0.0729 0.092 Uiso 1 1 calc R . . C22 C 0.4071(3) 0.0348(2) 0.08320(12) 0.0890(15) Uani 1 1 d . . . H22 H 0.3967 0.0208 0.0476 0.107 Uiso 1 1 calc R . . C23 C 0.3620(2) -0.03429(18) 0.11959(11) 0.0623(10) Uani 1 1 d . . . C24 C 0.3829(2) -0.0081(2) 0.17102(12) 0.0810(12) Uani 1 1 d . . . H24 H 0.3551 -0.0526 0.1974 0.097 Uiso 1 1 calc R . . C25 C 0.4447(3) 0.0837(2) 0.18403(12) 0.0850(13) Uani 1 1 d . . . H25 H 0.4572 0.1002 0.2193 0.102 Uiso 1 1 calc R . . C26 C 0.2583(3) -0.1643(2) 0.06178(13) 0.0942(15) Uani 1 1 d . . . C27 C 0.1836(2) -0.2655(2) 0.06040(12) 0.0736(12) Uani 1 1 d . . . C28 C 0.1361(5) -0.3049(4) 0.01686(18) 0.181(4) Uani 1 1 d . . . H28 H 0.1500 -0.2686 -0.0133 0.217 Uiso 1 1 calc R . . C29 C 0.0681(5) -0.3956(3) 0.01459(18) 0.200(4) Uani 1 1 d . . . H29 H 0.0403 -0.4196 -0.0178 0.240 Uiso 1 1 calc R . . C30 C 0.0393(2) -0.4514(2) 0.05480(12) 0.0662(10) Uani 1 1 d . . . C31 C 0.0978(3) -0.4166(3) 0.09481(17) 0.130(2) Uani 1 1 d . . . H31 H 0.0924 -0.4577 0.1214 0.156 Uiso 1 1 calc R . . C32 C 0.1653(3) -0.3255(3) 0.10023(18) 0.126(2) Uani 1 1 d . . . H32 H 0.1987 -0.3047 0.1315 0.151 Uiso 1 1 calc R . . N21 N 0.48714(15) 0.14971(15) 0.14734(9) 0.0576(7) Uani 1 1 d . . . N22 N 0.29677(18) -0.12808(16) 0.10803(9) 0.0709(9) Uani 1 1 d . . . H22A H 0.2797 -0.1666 0.1340 0.085 Uiso 1 1 calc R . . O11 O 0.62362(14) 0.33094(13) 0.09512(8) 0.0682(7) Uani 1 1 d . . . O12 O 0.69753(15) 0.46409(17) 0.13801(9) 0.0894(8) Uani 1 1 d . . . O13 O 0.8515(8) 0.7589(3) 0.03579(19) 0.502(9) Uani 1 1 d . . . O21 O 0.2786(3) -0.1184(2) 0.02275(11) 0.210(2) Uani 1 1 d . . . Zn1 Zn 0.57526(3) 0.287631(16) 0.1667 0.05223(11) Uani 1 2 d S . . 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 C11 0.0670(12) 0.0643(13) 0.0613(16) -0.0102(12) 0.0132(12) 0.0367(10) C12 0.0804(17) 0.0420(12) 0.0841(19) -0.0062(13) 0.0278(16) 0.0194(12) C13 0.0664(17) 0.0376(19) 0.070(2) 0.000 0.0240(18) 0.0188(10) C14 0.181(4) 0.0475(18) 0.139(3) -0.0272(19) 0.077(3) 0.011(2) C15 0.359(10) 0.043(3) 0.151(5) 0.000 0.143(6) 0.0217(15) C16 0.79(3) 0.066(5) 0.164(6) 0.000 0.207(11) 0.033(2) C21 0.101(2) 0.0502(15) 0.0462(15) 0.0036(12) -0.0056(15) 0.0135(15) C22 0.107(3) 0.0534(18) 0.0541(17) 0.0059(14) -0.0091(18) 0.0007(17) C23 0.0620(15) 0.0477(14) 0.0608(16) 0.0043(12) -0.0120(13) 0.0152(12) C24 0.0899(19) 0.0521(15) 0.0685(18) 0.0104(16) -0.0005(17) 0.0111(15) C25 0.113(2) 0.0679(18) 0.0564(17) 0.0013(14) -0.0060(16) 0.0318(17) C26 0.099(3) 0.0539(18) 0.071(2) 0.0176(16) -0.0132(18) -0.0059(18) C27 0.0719(18) 0.0582(17) 0.0619(18) 0.0047(14) -0.0082(15) 0.0110(15) C28 0.219(6) 0.087(3) 0.086(3) 0.001(2) -0.029(3) -0.036(4) C29 0.237(7) 0.090(3) 0.087(3) -0.012(2) -0.020(4) -0.057(4) C30 0.0521(14) 0.0520(14) 0.0828(19) 0.0046(14) -0.0011(15) 0.0172(11) C31 0.131(3) 0.069(2) 0.122(3) 0.029(2) -0.038(3) -0.001(2) C32 0.114(3) 0.067(2) 0.110(3) 0.013(2) -0.037(3) -0.019(2) N21 0.0622(11) 0.0467(10) 0.0626(14) 0.0009(9) 0.0015(10) 0.0264(8) N22 0.0731(14) 0.0459(12) 0.0679(14) 0.0149(11) -0.0075(13) 0.0105(11) O11 0.0779(10) 0.0618(10) 0.0561(10) 0.0049(8) 0.0186(9) 0.0283(8) O12 0.0837(12) 0.0990(14) 0.0764(13) -0.0273(11) 0.0111(11) 0.0388(11) O13 0.94(2) 0.086(3) 0.208(5) -0.016(3) 0.182(8) 0.054(7) O21 0.249(4) 0.0916(19) 0.0794(16) 0.0340(15) -0.054(2) -0.073(3) Zn1 0.0557(3) 0.05055(16) 0.0521(2) -0.00435(17) 0.000 0.02787(13) _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 C11 O12 1.235(4) . ? C11 O11 1.258(3) . ? C11 C12 1.512(4) . ? C12 C13 1.368(4) . ? C12 C14 1.388(4) . ? C13 C12 1.368(4) 11_655 ? C13 H13 0.9300 . ? C14 C15 1.347(5) . ? C14 H14 0.9300 . ? C15 C14 1.347(5) 11_655 ? C15 C16 1.447(10) . ? C16 O13 1.205(8) . ? C16 O13 1.205(8) 11_655 ? C21 N21 1.295(3) . ? C21 C22 1.361(4) . ? C21 H21 0.9300 . ? C22 C23 1.365(4) . ? C22 H22 0.9300 . ? C23 C24 1.367(4) . ? C23 N22 1.405(3) . ? C24 C25 1.379(4) . ? C24 H24 0.9300 . ? C25 N21 1.336(4) . ? C25 H25 0.9300 . ? C26 O21 1.192(4) . ? C26 N22 1.329(4) . ? C26 C27 1.501(4) . ? C27 C28 1.325(6) . ? C27 C32 1.341(5) . ? C28 C29 1.350(6) . ? C28 H28 0.9300 . ? C29 C30 1.298(5) . ? C29 H29 0.9300 . ? C30 C31 1.321(5) . ? C30 C30 1.474(5) 4_545 ? C31 C32 1.359(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? N21 Zn1 2.056(2) . ? N22 H22A 0.8600 . ? O11 Zn1 1.9731(19) . ? Zn1 O11 1.9731(19) 9 ? Zn1 N21 2.056(2) 9 ? 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 O12 C11 O11 123.6(3) . . ? O12 C11 C12 118.9(2) . . ? O11 C11 C12 117.5(2) . . ? C13 C12 C14 118.2(3) . . ? C13 C12 C11 122.3(3) . . ? C14 C12 C11 119.5(3) . . ? C12 C13 C12 121.1(4) . 11_655 ? C12 C13 H13 119.5 . . ? C12 C13 H13 119.5 11_655 . ? C15 C14 C12 121.6(4) . . ? C15 C14 H14 119.2 . . ? C12 C14 H14 119.2 . . ? C14 C15 C14 119.1(5) . 11_655 ? C14 C15 C16 120.4(3) . . ? C14 C15 C16 120.4(3) 11_655 . ? O13 C16 O13 115.9(8) . 11_655 ? O13 C16 C15 122.0(4) . . ? O13 C16 C15 122.0(4) 11_655 . ? N21 C21 C22 124.0(3) . . ? N21 C21 H21 118.0 . . ? C22 C21 H21 118.0 . . ? C21 C22 C23 120.3(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 116.1(2) . . ? C22 C23 N22 125.1(3) . . ? C24 C23 N22 118.8(2) . . ? C23 C24 C25 120.5(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? N21 C25 C24 121.7(3) . . ? N21 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? O21 C26 N22 122.2(3) . . ? O21 C26 C27 120.1(3) . . ? N22 C26 C27 117.6(3) . . ? C28 C27 C32 114.3(3) . . ? C28 C27 C26 121.4(3) . . ? C32 C27 C26 124.0(3) . . ? C27 C28 C29 122.6(5) . . ? C27 C28 H28 118.7 . . ? C29 C28 H28 118.7 . . ? C30 C29 C28 124.0(4) . . ? C30 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? C29 C30 C31 111.7(3) . . ? C29 C30 C30 125.7(3) . 4_545 ? C31 C30 C30 121.8(3) . 4_545 ? C30 C31 C32 125.2(4) . . ? C30 C31 H31 117.4 . . ? C32 C31 H31 117.4 . . ? C27 C32 C31 119.8(4) . . ? C27 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C21 N21 C25 117.3(2) . . ? C21 N21 Zn1 120.84(18) . . ? C25 N21 Zn1 121.82(19) . . ? C26 N22 C23 127.7(3) . . ? C26 N22 H22A 116.1 . . ? C23 N22 H22A 116.1 . . ? C11 O11 Zn1 107.83(18) . . ? O11 Zn1 O11 138.99(12) 9 . ? O11 Zn1 N21 96.57(8) 9 9 ? O11 Zn1 N21 108.35(10) . 9 ? O11 Zn1 N21 108.35(10) 9 . ? O11 Zn1 N21 96.57(8) . . ? N21 Zn1 N21 104.45(15) 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 O12 C11 C12 C13 171.4(3) . . . . ? O11 C11 C12 C13 -8.0(5) . . . . ? O12 C11 C12 C14 -7.7(6) . . . . ? O11 C11 C12 C14 172.8(4) . . . . ? C14 C12 C13 C12 -1.8(3) . . . 11_655 ? C11 C12 C13 C12 179.0(4) . . . 11_655 ? C13 C12 C14 C15 3.8(7) . . . . ? C11 C12 C14 C15 -177.1(4) . . . . ? C12 C14 C15 C14 -1.9(4) . . . 11_655 ? C12 C14 C15 C16 178.1(4) . . . . ? C14 C15 C16 O13 -17.4(8) . . . . ? C14 C15 C16 O13 162.6(8) 11_655 . . . ? C14 C15 C16 O13 162.6(8) . . . 11_655 ? C14 C15 C16 O13 -17.4(8) 11_655 . . 11_655 ? N21 C21 C22 C23 1.2(7) . . . . ? C21 C22 C23 C24 -1.4(6) . . . . ? C21 C22 C23 N22 178.2(4) . . . . ? C22 C23 C24 C25 1.3(6) . . . . ? N22 C23 C24 C25 -178.3(4) . . . . ? C23 C24 C25 N21 -0.9(7) . . . . ? O21 C26 C27 C28 -2.9(9) . . . . ? N22 C26 C27 C28 174.0(6) . . . . ? O21 C26 C27 C32 170.3(6) . . . . ? N22 C26 C27 C32 -12.7(7) . . . . ? C32 C27 C28 C29 6.5(11) . . . . ? C26 C27 C28 C29 -179.6(7) . . . . ? C27 C28 C29 C30 3.9(14) . . . . ? C28 C29 C30 C31 -15.0(11) . . . . ? C28 C29 C30 C30 175.1(7) . . . 4_545 ? C29 C30 C31 C32 17.2(9) . . . . ? C30 C30 C31 C32 -172.5(6) 4_545 . . . ? C28 C27 C32 C31 -4.6(9) . . . . ? C26 C27 C32 C31 -178.2(5) . . . . ? C30 C31 C32 C27 -7.9(10) . . . . ? C22 C21 N21 C25 -0.8(6) . . . . ? C22 C21 N21 Zn1 -177.7(4) . . . . ? C24 C25 N21 C21 0.6(6) . . . . ? C24 C25 N21 Zn1 177.5(3) . . . . ? O21 C26 N22 C23 2.2(8) . . . . ? C27 C26 N22 C23 -174.6(4) . . . . ? C22 C23 N22 C26 -9.2(7) . . . . ? C24 C23 N22 C26 170.3(4) . . . . ? O12 C11 O11 Zn1 3.4(4) . . . . ? C12 C11 O11 Zn1 -177.2(2) . . . . ? C11 O11 Zn1 O11 -55.6(2) . . . 9 ? C11 O11 Zn1 N21 68.8(2) . . . 9 ? C11 O11 Zn1 N21 176.4(2) . . . . ? C21 N21 Zn1 O11 -159.9(3) . . . 9 ? C25 N21 Zn1 O11 23.4(3) . . . 9 ? C21 N21 Zn1 O11 -12.9(3) . . . . ? C25 N21 Zn1 O11 170.3(3) . . . . ? C21 N21 Zn1 N21 98.0(3) . . . 9 ? C25 N21 Zn1 N21 -78.8(3) . . . 9 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.570 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.091