# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Caoyuan Niu' _publ_contact_author_email 'NIU CY2000@YAHOO.COM.CN' _publ_section_title ; Unusual Secondary Ligand's Tuning to Construct Fluorescent Zinc Coordination Polymers of An Unsymmetrical Pyridylbenzoate Ligand from 1D Chain to Interdigital or Porous 2D Layers and Interpenetrated 3D Diamondoid Frameworks ; loop_ _publ_author_name 'Caoyuan Niu' 'Zhi-Qiang Feng' 'Yong He' 'Chun-Hong Kou' 'Xianfu Zheng' # Attachment 'all.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 740526' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C120 H87 N10 O23.5 Zn5' _chemical_formula_weight 2363.92 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3213(8) _cell_length_b 11.3297(8) _cell_length_c 21.2344(14) _cell_angle_alpha 102.188(1) _cell_angle_beta 93.507(1) _cell_angle_gamma 99.410(1) _cell_volume 2613.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6970 _exptl_absorpt_correction_T_max 0.7194 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14689 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.50 _reflns_number_total 9606 _reflns_number_gt 7815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The bond lengths O12-H1W and O12-H2W were restrained to the target value of 0.82(2) \%A. Atoms O7, O8, C60, O9, and O10 are disordered over two positions. The bond lengths C48-O7 and C48-O8 were restrained to the target value of 1.22(2) \%A, C56-C60 to 1.52(2) \%A, C60-O9 and C60-O10 to 1.21(2) \%A. Displacement parameters for all disordered O and C atoms were also subjected to restraints. ; _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^)+(0.0716P)^2^+4.8462P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9606 _refine_ls_number_parameters 767 _refine_ls_number_restraints 159 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.51942(5) 0.27738(4) 1.08541(2) 0.03633(15) Uani 1 1 d . . . Zn2 Zn 0.5000 0.5000 1.0000 0.03382(18) Uani 1 2 d S . . Zn3 Zn 0.11996(7) 0.24337(7) 0.53367(3) 0.0640(2) Uani 1 1 d . . . O1 O 0.4015(3) 0.2005(3) 1.01043(14) 0.0459(8) Uani 1 1 d . A . O2 O 0.3660(3) 0.3505(3) 0.96174(14) 0.0433(7) Uani 1 1 d . A . O3 O 0.4803(3) -0.5352(3) 1.09603(15) 0.0520(8) Uani 1 1 d . . . O4 O 0.5425(5) -0.5982(3) 1.17783(18) 0.0846(15) Uani 1 1 d . . . O5 O 0.6821(3) 0.2855(3) 1.05485(16) 0.0501(8) Uani 1 1 d . . . O6 O 0.6248(3) 0.3890(3) 0.98409(16) 0.0491(8) Uani 1 1 d . . . O7 O 0.1055(14) 0.0654(17) 0.4719(6) 0.095(4) Uani 0.483(7) 1 d PDU A 1 O7' O 0.1587(17) 0.076(2) 0.4723(9) 0.150(8) Uani 0.517(7) 1 d PDU A 2 O8 O 0.1026(16) 0.2108(15) 0.4259(11) 0.091(5) Uani 0.483(7) 1 d PDU A 1 O8' O 0.0637(18) 0.1977(17) 0.4165(12) 0.113(7) Uani 0.483(7) 1 d PDU A 2 O9 O -0.6922(6) 0.3392(7) 0.5456(3) 0.0307(17) Uani 0.483(7) 1 d PDU . 1 O10 O -0.7536(7) 0.4930(8) 0.6086(5) 0.078(3) Uani 0.483(7) 1 d PDU . 1 C60 C -0.6827(8) 0.4402(10) 0.5797(5) 0.053(3) Uani 0.483(7) 1 d PDU . 1 O10' O -0.7735(7) 0.3807(8) 0.5520(4) 0.074(3) Uani 0.517(7) 1 d PDU . 2 O9' O -0.6751(7) 0.2405(9) 0.5326(4) 0.082(3) Uani 0.517(7) 1 d PDU . 2 C60' C -0.6676(13) 0.3691(15) 0.5539(17) 0.159(16) Uani 0.517(7) 1 d PDU . 2 O11 O 0.401(2) 0.001(2) 0.5357(12) 0.116(7) Uani 0.25 1 d PU . . O12 O 0.8511(13) 0.2744(12) 0.3454(5) 0.195(4) Uani 1 1 d DU . . O13 O 0.6458(14) 0.1500(15) 0.3758(8) 0.161(5) Uani 0.50 1 d PU . . N1 N 0.1251(4) 0.1858(4) 0.62001(18) 0.0483(9) Uani 1 1 d . A . N2 N 0.4969(3) 0.1319(3) 1.12965(16) 0.0368(8) Uani 1 1 d . . . N3 N 1.0080(8) 0.5831(6) 0.7440(3) 0.102(2) Uani 1 1 d . . . N4 N 0.1383(7) 0.1333(7) 0.0729(3) 0.0944(19) Uani 1 1 d . . . N5 N -0.0299(4) 0.3258(4) 0.5393(2) 0.0575(11) Uani 1 1 d . A . C1 C 0.1512(5) 0.0759(5) 0.6233(2) 0.0508(12) Uani 1 1 d . . . H1 H 0.1579 0.0197 0.5841 0.061 Uiso 1 1 calc R A . C2 C 0.1687(5) 0.0411(4) 0.6805(2) 0.0488(11) Uani 1 1 d . A . H2 H 0.1872 -0.0378 0.6803 0.059 Uiso 1 1 calc R . . C3 C 0.1598(4) 0.1202(4) 0.7389(2) 0.0388(9) Uani 1 1 d . . . C4 C 0.1317(5) 0.2327(5) 0.7351(2) 0.0540(13) Uani 1 1 d . A . H4 H 0.1239 0.2903 0.7735 0.065 Uiso 1 1 calc R . . C5 C 0.1149(6) 0.2618(5) 0.6759(2) 0.0612(14) Uani 1 1 d . . . H5 H 0.0952 0.3397 0.6748 0.073 Uiso 1 1 calc R A . C6 C 0.1839(4) 0.0872(4) 0.8020(2) 0.0371(9) Uani 1 1 d . A . C7 C 0.1544(4) -0.0337(4) 0.8082(2) 0.0449(10) Uani 1 1 d . . . H7 H 0.1140 -0.0956 0.7726 0.054 Uiso 1 1 calc R A . C8 C 0.1839(5) -0.0638(4) 0.8665(2) 0.0497(12) Uani 1 1 d . A . H8 H 0.1615 -0.1461 0.8708 0.060 Uiso 1 1 calc R . . C9 C 0.2451(4) 0.0237(4) 0.9181(2) 0.0436(10) Uani 1 1 d . . . H9 H 0.2664 0.0015 0.9574 0.052 Uiso 1 1 calc R A . C10 C 0.2760(4) 0.1454(4) 0.91267(19) 0.0364(9) Uani 1 1 d . A . C11 C 0.2428(4) 0.1764(4) 0.85508(19) 0.0353(9) Uani 1 1 d . . . H11 H 0.2604 0.2597 0.8518 0.042 Uiso 1 1 calc R A . C12 C 0.3527(4) 0.2411(4) 0.9662(2) 0.0377(9) Uani 1 1 d . . . C13 C 0.4431(4) 0.0191(4) 1.0973(2) 0.0416(10) Uani 1 1 d . . . H13 H 0.4082 0.0090 1.0542 0.050 Uiso 1 1 calc R . . C14 C 0.4362(4) -0.0826(4) 1.1237(2) 0.0423(10) Uani 1 1 d . . . H14 H 0.3963 -0.1606 1.0991 0.051 Uiso 1 1 calc R . . C15 C 0.4878(4) -0.0709(4) 1.18648(19) 0.0341(9) Uani 1 1 d . . . C16 C 0.5397(5) 0.0465(4) 1.2203(2) 0.0453(11) Uani 1 1 d . . . H16 H 0.5736 0.0598 1.2638 0.054 Uiso 1 1 calc R . . C17 C 0.5420(5) 0.1438(4) 1.1907(2) 0.0475(11) Uani 1 1 d . . . H17 H 0.5775 0.2235 1.2149 0.057 Uiso 1 1 calc R . . C18 C 0.4929(4) -0.1799(4) 1.21463(19) 0.0351(9) Uani 1 1 d . . . C19 C 0.5108(5) -0.1688(4) 1.2810(2) 0.0497(12) Uani 1 1 d . . . H19 H 0.5129 -0.0912 1.3094 0.060 Uiso 1 1 calc R . . C20 C 0.5255(6) -0.2681(4) 1.3066(2) 0.0625(15) Uani 1 1 d . . . H20 H 0.5363 -0.2587 1.3522 0.075 Uiso 1 1 calc R . . C21 C 0.5246(6) -0.3810(4) 1.2663(2) 0.0584(14) Uani 1 1 d . . . H21 H 0.5377 -0.4487 1.2840 0.070 Uiso 1 1 calc R . . C22 C 0.5043(4) -0.3950(4) 1.1994(2) 0.0403(10) Uani 1 1 d . . . C23 C 0.4866(4) -0.2955(4) 1.17437(19) 0.0349(9) Uani 1 1 d . . . H23 H 0.4700 -0.3061 1.1289 0.042 Uiso 1 1 calc R . . C24 C 0.5093(5) -0.5148(4) 1.1557(2) 0.0455(11) Uani 1 1 d . . . C25 C 1.0960(9) 0.5806(6) 0.7868(4) 0.098(3) Uani 1 1 d . . . H25 H 1.1746 0.6191 0.7815 0.118 Uiso 1 1 calc R . . C26 C 1.0824(7) 0.5257(5) 0.8393(3) 0.0742(18) Uani 1 1 d . . . H26 H 1.1499 0.5276 0.8685 0.089 Uiso 1 1 calc R . . C27 C 0.9683(5) 0.4680(4) 0.8484(2) 0.0560(13) Uani 1 1 d . . . C28 C 0.8757(7) 0.4700(6) 0.8033(3) 0.0735(17) Uani 1 1 d . . . H28 H 0.7960 0.4316 0.8068 0.088 Uiso 1 1 calc R . . C29 C 0.8993(9) 0.5282(8) 0.7529(4) 0.097(2) Uani 1 1 d . . . H29 H 0.8337 0.5288 0.7229 0.116 Uiso 1 1 calc R . . C30 C 0.9490(5) 0.4077(4) 0.9035(2) 0.0477(11) Uani 1 1 d . . . C31 C 1.0405(5) 0.3615(5) 0.9317(3) 0.0551(12) Uani 1 1 d . . . H31 H 1.1173 0.3691 0.9156 0.066 Uiso 1 1 calc R . . C32 C 1.0214(5) 0.3047(5) 0.9827(3) 0.0568(13) Uani 1 1 d . . . H32 H 1.0846 0.2729 1.0009 0.068 Uiso 1 1 calc R . . C33 C 0.9112(4) 0.2939(4) 1.0072(2) 0.0471(11) Uani 1 1 d . . . H33 H 0.8985 0.2539 1.0419 0.056 Uiso 1 1 calc R . . C34 C 0.8189(4) 0.3414(4) 0.9812(2) 0.0403(10) Uani 1 1 d . . . C35 C 0.8384(4) 0.3979(4) 0.9290(2) 0.0434(10) Uani 1 1 d . . . H35 H 0.7752 0.4299 0.9109 0.052 Uiso 1 1 calc R . . C36 C 0.7009(4) 0.3395(4) 1.0088(2) 0.0381(9) Uani 1 1 d . . . C37 C 0.1861(9) 0.2084(7) 0.1291(4) 0.101(3) Uani 1 1 d . . . H37 H 0.2125 0.2926 0.1295 0.121 Uiso 1 1 calc R . . C38 C 0.1999(7) 0.1712(6) 0.1872(3) 0.0802(19) Uani 1 1 d . . . H38 H 0.2342 0.2286 0.2259 0.096 Uiso 1 1 calc R . . C39 C 0.1624(5) 0.0487(5) 0.1872(2) 0.0551(13) Uani 1 1 d . . . C40 C 0.1167(5) -0.0282(6) 0.1282(3) 0.0657(15) Uani 1 1 d . . . H40 H 0.0921 -0.1136 0.1252 0.079 Uiso 1 1 calc R . . C41 C 0.1064(7) 0.0181(7) 0.0739(3) 0.0781(18) Uani 1 1 d . . . H41 H 0.0739 -0.0376 0.0343 0.094 Uiso 1 1 calc R . . C42 C 0.1699(4) 0.0024(5) 0.2467(2) 0.0524(12) Uani 1 1 d . . . C43 C 0.2012(5) -0.1117(6) 0.2460(3) 0.0631(14) Uani 1 1 d . . . H43 H 0.2183 -0.1604 0.2065 0.076 Uiso 1 1 calc R . . C44 C 0.2075(7) -0.1543(7) 0.3018(3) 0.086(2) Uani 1 1 d . . . H44 H 0.2286 -0.2323 0.3010 0.103 Uiso 1 1 calc R . . C45 C 0.1826(7) -0.0824(8) 0.3595(3) 0.089(2) Uani 1 1 d . . . H45 H 0.1884 -0.1112 0.3983 0.107 Uiso 1 1 calc R . . C46 C 0.1499(6) 0.0292(7) 0.3610(3) 0.0743(18) Uani 1 1 d . A . C47 C 0.1442(5) 0.0712(6) 0.3051(3) 0.0645(15) Uani 1 1 d . . . H47 H 0.1221 0.1489 0.3061 0.077 Uiso 1 1 calc R . . C48 C 0.1177(8) 0.1107(11) 0.4239(4) 0.105(3) Uani 1 1 d D . . C49 C -0.0235(5) 0.4392(6) 0.5687(4) 0.0769(18) Uani 1 1 d . . . H49 H 0.0542 0.4865 0.5838 0.092 Uiso 1 1 calc R A . C50 C -0.1209(5) 0.4965(6) 0.5797(3) 0.0733(18) Uani 1 1 d . A . H50 H -0.1082 0.5808 0.6009 0.088 Uiso 1 1 calc R . . C51 C -0.2343(4) 0.4345(5) 0.5608(2) 0.0500(12) Uani 1 1 d U . . C52 C -0.2412(7) 0.3172(7) 0.5274(5) 0.106(3) Uani 1 1 d U A . H52 H -0.3177 0.2689 0.5107 0.127 Uiso 1 1 calc R . . C53 C -0.1398(8) 0.2671(7) 0.5175(4) 0.106(3) Uani 1 1 d U . . H53 H -0.1494 0.1848 0.4933 0.127 Uiso 1 1 calc R A . C54 C -0.3408(3) 0.4929(4) 0.5770(2) 0.0642(15) Uani 1 1 d GU A . C55 C -0.4561(3) 0.4233(4) 0.5633(2) 0.086(2) Uani 1 1 d GDU . . H55 H -0.4675 0.3390 0.5421 0.103 Uiso 1 1 calc R A . C56 C -0.5548(3) 0.4771(6) 0.5806(2) 0.114(3) Uani 1 1 d GDU . . C57 C -0.5381(4) 0.6004(6) 0.6116(3) 0.141(4) Uani 1 1 d GDU . . H57 H -0.6055 0.6372 0.6234 0.170 Uiso 1 1 calc R A . C58 C -0.4227(5) 0.6700(4) 0.6253(3) 0.138(4) Uani 1 1 d GU A . H58 H -0.4113 0.7543 0.6465 0.166 Uiso 1 1 calc R . . C59 C -0.3241(4) 0.6163(4) 0.6080(2) 0.093(2) Uani 1 1 d GU . . H59 H -0.2452 0.6638 0.6174 0.112 Uiso 1 1 calc R A . H1W H 0.809(6) 0.276(10) 0.315(3) 0.112 Uiso 1 1 d D . . H2W H 0.915(4) 0.264(10) 0.334(4) 0.112 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0518(3) 0.0272(3) 0.0314(3) 0.01058(19) -0.0018(2) 0.0083(2) Zn2 0.0463(4) 0.0276(3) 0.0300(3) 0.0095(3) 0.0002(3) 0.0111(3) Zn3 0.0879(5) 0.0834(5) 0.0365(3) 0.0217(3) 0.0142(3) 0.0475(4) O1 0.059(2) 0.0398(17) 0.0376(16) 0.0148(13) -0.0104(14) 0.0036(14) O2 0.0556(19) 0.0331(16) 0.0398(16) 0.0096(13) -0.0089(14) 0.0072(13) O3 0.083(2) 0.0393(17) 0.0323(17) 0.0059(13) 0.0040(16) 0.0117(16) O4 0.176(5) 0.0361(19) 0.049(2) 0.0120(16) -0.001(3) 0.042(2) O5 0.0510(19) 0.057(2) 0.0484(19) 0.0249(16) 0.0027(15) 0.0106(15) O6 0.056(2) 0.0500(19) 0.0509(19) 0.0186(15) 0.0101(15) 0.0247(16) O7 0.100(8) 0.145(9) 0.039(5) 0.015(5) 0.030(5) 0.014(7) O7' 0.151(12) 0.184(11) 0.106(10) 0.022(8) 0.051(8) 0.004(9) O8 0.084(7) 0.092(7) 0.076(7) -0.023(5) 0.028(6) 0.004(6) O8' 0.117(11) 0.107(10) 0.092(10) -0.012(7) 0.052(9) -0.011(7) O9 0.023(3) 0.039(4) 0.028(3) 0.008(3) 0.005(2) -0.002(3) O10 0.039(4) 0.082(6) 0.115(7) 0.023(5) 0.014(4) 0.011(4) C60 0.047(6) 0.074(7) 0.053(6) 0.034(5) 0.013(5) 0.020(5) O10' 0.045(4) 0.099(6) 0.082(5) 0.045(5) -0.007(4) -0.006(4) O9' 0.054(4) 0.111(7) 0.072(5) 0.017(5) 0.004(4) -0.004(4) C60' 0.166(19) 0.168(18) 0.154(18) 0.049(11) 0.023(10) 0.040(11) O11 0.122(11) 0.100(10) 0.117(11) -0.003(8) 0.013(9) 0.033(9) O12 0.261(9) 0.126(6) 0.188(7) 0.027(6) 0.055(7) 0.005(7) O13 0.151(9) 0.164(9) 0.148(9) -0.025(7) -0.012(7) 0.064(8) N1 0.062(3) 0.054(2) 0.0327(19) 0.0109(17) 0.0044(17) 0.021(2) N2 0.051(2) 0.0300(18) 0.0322(18) 0.0122(14) 0.0019(15) 0.0108(15) N3 0.160(7) 0.080(4) 0.073(4) 0.031(3) 0.041(4) 0.012(4) N4 0.133(6) 0.101(5) 0.066(4) 0.027(3) 0.020(4) 0.058(4) N5 0.073(3) 0.069(3) 0.038(2) 0.013(2) 0.003(2) 0.031(2) C1 0.062(3) 0.056(3) 0.033(2) 0.006(2) 0.004(2) 0.014(2) C2 0.069(3) 0.043(3) 0.035(2) 0.006(2) 0.003(2) 0.015(2) C3 0.037(2) 0.045(2) 0.033(2) 0.0062(18) 0.0025(17) 0.0080(18) C4 0.082(4) 0.052(3) 0.031(2) 0.006(2) 0.004(2) 0.028(3) C5 0.095(4) 0.058(3) 0.041(3) 0.014(2) 0.008(3) 0.042(3) C6 0.037(2) 0.043(2) 0.033(2) 0.0098(18) 0.0037(17) 0.0091(18) C7 0.053(3) 0.040(2) 0.037(2) 0.0065(19) -0.001(2) 0.002(2) C8 0.066(3) 0.036(2) 0.043(3) 0.011(2) 0.001(2) 0.000(2) C9 0.054(3) 0.043(2) 0.035(2) 0.0147(19) 0.0010(19) 0.004(2) C10 0.039(2) 0.038(2) 0.032(2) 0.0076(17) 0.0024(17) 0.0070(18) C11 0.037(2) 0.037(2) 0.033(2) 0.0091(17) 0.0034(17) 0.0089(17) C12 0.041(2) 0.039(2) 0.033(2) 0.0091(18) 0.0025(17) 0.0069(18) C13 0.060(3) 0.033(2) 0.032(2) 0.0106(18) -0.0035(19) 0.010(2) C14 0.062(3) 0.028(2) 0.035(2) 0.0066(17) -0.005(2) 0.0049(19) C15 0.044(2) 0.032(2) 0.031(2) 0.0108(17) 0.0088(17) 0.0140(17) C16 0.072(3) 0.032(2) 0.032(2) 0.0085(18) -0.005(2) 0.010(2) C17 0.076(3) 0.027(2) 0.037(2) 0.0075(18) -0.007(2) 0.008(2) C18 0.046(2) 0.032(2) 0.032(2) 0.0121(17) 0.0073(17) 0.0115(18) C19 0.087(4) 0.033(2) 0.031(2) 0.0071(18) 0.010(2) 0.016(2) C20 0.120(5) 0.041(3) 0.031(2) 0.014(2) 0.006(3) 0.020(3) C21 0.111(5) 0.032(2) 0.036(2) 0.016(2) 0.002(3) 0.016(3) C22 0.059(3) 0.029(2) 0.034(2) 0.0095(17) 0.0051(19) 0.0086(19) C23 0.048(2) 0.031(2) 0.0272(19) 0.0089(16) 0.0041(17) 0.0079(17) C24 0.072(3) 0.029(2) 0.036(2) 0.0101(18) 0.007(2) 0.008(2) C25 0.146(8) 0.065(4) 0.071(5) 0.001(4) 0.047(5) -0.016(4) C26 0.099(5) 0.060(3) 0.053(3) 0.000(3) 0.026(3) -0.007(3) C27 0.083(4) 0.038(3) 0.047(3) 0.007(2) 0.020(3) 0.010(2) C28 0.099(5) 0.076(4) 0.057(3) 0.028(3) 0.020(3) 0.027(4) C29 0.132(7) 0.105(6) 0.069(4) 0.040(4) 0.024(4) 0.037(5) C30 0.062(3) 0.036(2) 0.044(3) 0.006(2) 0.010(2) 0.008(2) C31 0.056(3) 0.055(3) 0.053(3) 0.006(2) 0.014(2) 0.015(2) C32 0.053(3) 0.060(3) 0.060(3) 0.011(3) 0.001(2) 0.023(2) C33 0.057(3) 0.045(3) 0.042(2) 0.011(2) 0.002(2) 0.016(2) C34 0.051(3) 0.033(2) 0.035(2) 0.0048(18) 0.0018(19) 0.0107(19) C35 0.055(3) 0.036(2) 0.040(2) 0.0085(19) 0.003(2) 0.012(2) C36 0.047(2) 0.031(2) 0.035(2) 0.0042(17) -0.0004(18) 0.0069(18) C37 0.145(8) 0.072(5) 0.098(6) 0.031(4) 0.031(5) 0.037(5) C38 0.110(5) 0.067(4) 0.064(4) 0.007(3) 0.019(4) 0.022(4) C39 0.057(3) 0.065(3) 0.047(3) 0.006(2) 0.014(2) 0.024(3) C40 0.075(4) 0.077(4) 0.047(3) 0.010(3) 0.005(3) 0.025(3) C41 0.100(5) 0.084(5) 0.055(4) 0.010(3) 0.001(3) 0.041(4) C42 0.048(3) 0.068(3) 0.037(2) 0.002(2) 0.010(2) 0.010(2) C43 0.069(4) 0.076(4) 0.046(3) 0.007(3) 0.014(3) 0.023(3) C44 0.108(6) 0.092(5) 0.068(4) 0.027(4) 0.017(4) 0.033(4) C45 0.098(5) 0.121(7) 0.049(4) 0.027(4) 0.009(3) 0.010(5) C46 0.076(4) 0.089(5) 0.045(3) -0.003(3) 0.017(3) -0.002(4) C47 0.068(4) 0.068(4) 0.050(3) -0.003(3) 0.019(3) 0.007(3) C48 0.101(6) 0.149(9) 0.052(4) 0.020(5) 0.018(4) -0.015(6) C49 0.043(3) 0.073(4) 0.105(5) -0.002(4) 0.000(3) 0.014(3) C50 0.047(3) 0.058(3) 0.102(5) -0.013(3) 0.000(3) 0.014(3) C51 0.043(3) 0.063(3) 0.049(3) 0.025(2) 0.003(2) 0.011(2) C52 0.073(4) 0.075(4) 0.151(7) 0.002(4) -0.030(4) 0.004(4) C53 0.110(6) 0.067(4) 0.126(6) -0.012(4) -0.027(5) 0.033(4) C54 0.044(3) 0.102(4) 0.064(3) 0.051(3) 0.012(2) 0.019(3) C55 0.049(3) 0.153(6) 0.076(4) 0.082(4) 0.002(3) 0.003(3) C56 0.045(3) 0.233(8) 0.102(5) 0.125(6) 0.012(3) 0.018(4) C57 0.109(6) 0.223(9) 0.150(7) 0.117(7) 0.052(5) 0.086(6) C58 0.132(7) 0.166(8) 0.162(8) 0.073(6) 0.073(6) 0.090(6) C59 0.084(4) 0.106(5) 0.117(5) 0.050(4) 0.046(4) 0.051(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 Zn1 O1 1.962(3) . ? Zn1 O5 1.985(3) . ? Zn1 N2 2.051(3) . ? Zn1 O4 2.134(4) 1_565 ? Zn1 O3 2.207(3) 1_565 ? Zn1 C24 2.532(4) 1_565 ? Zn2 O6 2.038(3) 2_667 ? Zn2 O6 2.038(3) . ? Zn2 O2 2.063(3) . ? Zn2 O2 2.063(3) 2_667 ? Zn2 O3 2.176(3) 1_565 ? Zn2 O3 2.176(3) 2_657 ? Zn3 O10' 1.761(8) 1_655 ? Zn3 N5 2.064(4) . ? Zn3 N1 2.072(4) . ? Zn3 O7 2.136(18) . ? Zn3 O7' 2.19(2) . ? Zn3 O9 2.197(7) 1_655 ? Zn3 O8 2.23(2) . ? Zn3 O9' 2.327(8) 1_655 ? Zn3 O8' 2.45(2) . ? Zn3 C60' 2.548(13) 1_655 ? O1 C12 1.265(5) . ? O2 C12 1.249(5) . ? O3 C24 1.253(5) . ? O3 Zn2 2.177(3) 1_545 ? O3 Zn1 2.207(3) 1_545 ? O4 C24 1.239(6) . ? O4 Zn1 2.135(4) 1_545 ? O5 C36 1.270(5) . ? O6 C36 1.248(5) . ? O7 C48 1.238(14) . ? O7' C48 1.263(17) . ? O8 C48 1.168(16) . ? O8' C48 1.274(17) . ? O9 C60 1.203(12) . ? O9 Zn3 2.197(7) 1_455 ? O10 C60 1.201(11) . ? C60 C56 1.437(9) . ? O10' C60' 1.226(15) . ? O10' Zn3 1.761(8) 1_455 ? O9' C60' 1.418(16) . ? O9' Zn3 2.327(8) 1_455 ? C60' C56 1.599(12) . ? C60' Zn3 2.548(13) 1_455 ? O12 H1W 0.80(2) . ? O12 H2W 0.80(2) . ? N1 C5 1.335(6) . ? N1 C1 1.341(6) . ? N2 C17 1.334(5) . ? N2 C13 1.341(6) . ? N3 C25 1.315(11) . ? N3 C29 1.328(11) . ? N4 C41 1.301(9) . ? N4 C37 1.334(10) . ? N5 C49 1.292(7) . ? N5 C53 1.317(9) . ? C1 C2 1.367(7) . ? C1 H1 0.9500 . ? C2 C3 1.388(6) . ? C2 H2 0.9500 . ? C3 C4 1.381(7) . ? C3 C6 1.487(6) . ? C4 C5 1.374(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.392(6) . ? C6 C11 1.394(6) . ? C7 C8 1.388(6) . ? C7 H7 0.9500 . ? C8 C9 1.373(6) . ? C8 H8 0.9500 . ? C9 C10 1.396(6) . ? C9 H9 0.9500 . ? C10 C11 1.389(6) . ? C10 C12 1.507(6) . ? C11 H11 0.9500 . ? C13 C14 1.377(6) . ? C13 H13 0.9500 . ? C14 C15 1.394(6) . ? C14 H14 0.9500 . ? C15 C16 1.386(6) . ? C15 C18 1.488(5) . ? C16 C17 1.377(6) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.388(6) . ? C18 C23 1.393(6) . ? C19 C20 1.377(6) . ? C19 H19 0.9500 . ? C20 C21 1.379(7) . ? C20 H20 0.9500 . ? C21 C22 1.398(6) . ? C21 H21 0.9500 . ? C22 C23 1.380(6) . ? C22 C24 1.485(6) . ? C23 H23 0.9500 . ? C24 Zn1 2.532(4) 1_545 ? C25 C26 1.391(10) . ? C25 H25 0.9500 . ? C26 C27 1.392(8) . ? C26 H26 0.9500 . ? C27 C28 1.383(9) . ? C27 C30 1.485(7) . ? C28 C29 1.388(9) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C35 1.393(7) . ? C30 C31 1.393(7) . ? C31 C32 1.382(8) . ? C31 H31 0.9500 . ? C32 C33 1.377(7) . ? C32 H32 0.9500 . ? C33 C34 1.388(6) . ? C33 H33 0.9500 . ? C34 C35 1.402(6) . ? C34 C36 1.490(6) . ? C35 H35 0.9500 . ? C37 C38 1.395(10) . ? C37 H37 0.9500 . ? C38 C39 1.383(8) . ? C38 H38 0.9500 . ? C39 C40 1.381(8) . ? C39 C42 1.471(7) . ? C40 C41 1.370(8) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 C47 1.392(7) . ? C42 C43 1.392(8) . ? C43 C44 1.373(8) . ? C43 H43 0.9500 . ? C44 C45 1.393(10) . ? C44 H44 0.9500 . ? C45 C46 1.370(10) . ? C45 H45 0.9500 . ? C46 C47 1.372(9) . ? C46 C48 1.555(11) . ? C47 H47 0.9500 . ? C49 C50 1.376(8) . ? C49 H49 0.9500 . ? C50 C51 1.351(7) . ? C50 H50 0.9500 . ? C51 C52 1.355(9) . ? C51 C54 1.491(6) . ? C52 C53 1.370(11) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C54 C55 1.3900 . ? C54 C59 1.3900 . ? C55 C56 1.3900 . ? C55 H55 0.9500 . ? C56 C57 1.3900 . ? C57 C58 1.3900 . ? C57 H57 0.9500 . ? C58 C59 1.3900 . ? C58 H58 0.9500 . ? C59 H59 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O5 107.73(14) . . ? O1 Zn1 N2 96.36(13) . . ? O5 Zn1 N2 105.53(14) . . ? O1 Zn1 O4 142.79(18) . 1_565 ? O5 Zn1 O4 105.71(19) . 1_565 ? N2 Zn1 O4 89.98(14) . 1_565 ? O1 Zn1 O3 96.44(13) . 1_565 ? O5 Zn1 O3 105.30(14) . 1_565 ? N2 Zn1 O3 141.00(13) . 1_565 ? O4 Zn1 O3 58.89(12) 1_565 1_565 ? O1 Zn1 C24 121.57(15) . 1_565 ? O5 Zn1 C24 107.97(16) . 1_565 ? N2 Zn1 C24 116.26(14) . 1_565 ? O4 Zn1 C24 29.23(14) 1_565 1_565 ? O3 Zn1 C24 29.66(13) 1_565 1_565 ? O6 Zn2 O6 179.998(2) 2_667 . ? O6 Zn2 O2 90.58(13) 2_667 . ? O6 Zn2 O2 89.42(13) . . ? O6 Zn2 O2 89.42(13) 2_667 2_667 ? O6 Zn2 O2 90.58(13) . 2_667 ? O2 Zn2 O2 180.0 . 2_667 ? O6 Zn2 O3 88.41(13) 2_667 1_565 ? O6 Zn2 O3 91.59(13) . 1_565 ? O2 Zn2 O3 89.55(12) . 1_565 ? O2 Zn2 O3 90.45(12) 2_667 1_565 ? O6 Zn2 O3 91.59(13) 2_667 2_657 ? O6 Zn2 O3 88.40(13) . 2_657 ? O2 Zn2 O3 90.45(12) . 2_657 ? O2 Zn2 O3 89.55(12) 2_667 2_657 ? O3 Zn2 O3 179.999(1) 1_565 2_657 ? O10' Zn3 N5 96.1(3) 1_655 . ? O10' Zn3 N1 102.7(3) 1_655 . ? N5 Zn3 N1 101.24(16) . . ? O10' Zn3 O7 136.0(5) 1_655 . ? N5 Zn3 O7 118.8(4) . . ? N1 Zn3 O7 96.2(3) . . ? O10' Zn3 O7' 121.2(6) 1_655 . ? N5 Zn3 O7' 133.3(5) . . ? N1 Zn3 O7' 97.0(5) . . ? O7 Zn3 O7' 15.7(6) . . ? O10' Zn3 O9 29.8(3) 1_655 1_655 ? N5 Zn3 O9 125.8(2) . 1_655 ? N1 Zn3 O9 96.6(2) . 1_655 ? O7 Zn3 O9 109.4(4) . 1_655 ? O7' Zn3 O9 93.7(5) . 1_655 ? O10' Zn3 O8 99.1(5) 1_655 . ? N5 Zn3 O8 91.6(4) . . ? N1 Zn3 O8 153.2(4) . . ? O7 Zn3 O8 57.1(5) . . ? O7' Zn3 O8 58.0(6) . . ? O9 Zn3 O8 94.6(5) 1_655 . ? O10' Zn3 O9' 59.0(3) 1_655 1_655 ? N5 Zn3 O9' 154.8(3) . 1_655 ? N1 Zn3 O9' 88.7(3) . 1_655 ? O7 Zn3 O9' 82.5(5) . 1_655 ? O7' Zn3 O9' 66.9(6) . 1_655 ? O9 Zn3 O9' 29.1(3) 1_655 1_655 ? O8 Zn3 O9' 89.4(5) . 1_655 ? O10' Zn3 O8' 106.4(5) 1_655 . ? N5 Zn3 O8' 84.3(4) . . ? N1 Zn3 O8' 149.6(5) . . ? O7 Zn3 O8' 56.3(5) . . ? O7' Zn3 O8' 60.3(6) . . ? O9 Zn3 O8' 104.2(5) 1_655 . ? O8 Zn3 O8' 9.9(8) . . ? O9' Zn3 O8' 98.9(5) 1_655 . ? O10' Zn3 C60' 25.6(4) 1_655 1_655 ? N5 Zn3 C60' 121.7(4) . 1_655 ? N1 Zn3 C60' 95.7(8) . 1_655 ? O7 Zn3 C60' 114.1(6) . 1_655 ? O7' Zn3 C60' 98.5(7) . 1_655 ? O9 Zn3 C60' 4.7(5) 1_655 1_655 ? O8 Zn3 C60' 97.4(9) . 1_655 ? O9' Zn3 C60' 33.4(4) 1_655 1_655 ? O8' Zn3 C60' 106.8(9) . 1_655 ? C12 O1 Zn1 133.4(3) . . ? C12 O2 Zn2 132.1(3) . . ? C24 O3 Zn2 153.2(3) . 1_545 ? C24 O3 Zn1 89.7(3) . 1_545 ? Zn2 O3 Zn1 102.95(13) 1_545 1_545 ? C24 O4 Zn1 93.5(3) . 1_545 ? C36 O5 Zn1 116.3(3) . . ? C36 O6 Zn2 146.6(3) . . ? C48 O7 Zn3 91.0(11) . . ? C48 O7' Zn3 88.0(13) . . ? C48 O8 Zn3 88.3(13) . . ? C48 O8' Zn3 76.6(12) . . ? C60 O9 Zn3 110.3(6) . 1_455 ? O10 C60 O9 132.4(9) . . ? O10 C60 C56 129.5(9) . . ? O9 C60 C56 97.9(7) . . ? C60' O10' Zn3 115.9(9) . 1_455 ? C60' O9' Zn3 81.8(7) . 1_455 ? O10' C60' O9' 102.9(10) . . ? O10' C60' C56 125.6(13) . . ? O9' C60' C56 131.3(12) . . ? O10' C60' Zn3 38.4(6) . 1_455 ? O9' C60' Zn3 64.7(6) . 1_455 ? C56 C60' Zn3 162.3(12) . 1_455 ? H1W O12 H2W 107(4) . . ? C5 N1 C1 116.9(4) . . ? C5 N1 Zn3 121.1(3) . . ? C1 N1 Zn3 121.7(3) . . ? C17 N2 C13 117.0(4) . . ? C17 N2 Zn1 121.4(3) . . ? C13 N2 Zn1 121.5(3) . . ? C25 N3 C29 115.9(7) . . ? C41 N4 C37 116.1(6) . . ? C49 N5 C53 114.4(5) . . ? C49 N5 Zn3 121.8(4) . . ? C53 N5 Zn3 123.7(4) . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 120.5(5) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 116.2(4) . . ? C4 C3 C6 122.0(4) . . ? C2 C3 C6 121.8(4) . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 123.2(5) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C7 C6 C11 119.0(4) . . ? C7 C6 C3 120.8(4) . . ? C11 C6 C3 120.1(4) . . ? C8 C7 C6 120.0(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.9(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 119.2(4) . . ? C11 C10 C12 119.5(4) . . ? C9 C10 C12 121.1(4) . . ? C10 C11 C6 121.0(4) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? O2 C12 O1 126.3(4) . . ? O2 C12 C10 118.0(4) . . ? O1 C12 C10 115.6(4) . . ? N2 C13 C14 123.0(4) . . ? N2 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C15 119.8(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 116.7(4) . . ? C16 C15 C18 121.5(4) . . ? C14 C15 C18 121.7(4) . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N2 C17 C16 123.4(4) . . ? N2 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C19 C18 C23 118.1(4) . . ? C19 C18 C15 121.4(4) . . ? C23 C18 C15 120.4(4) . . ? C20 C19 C18 121.2(4) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 119.7(4) . . ? C23 C22 C24 120.7(4) . . ? C21 C22 C24 119.5(4) . . ? C22 C23 C18 121.1(4) . . ? C22 C23 H23 119.4 . . ? C18 C23 H23 119.4 . . ? O4 C24 O3 118.0(4) . . ? O4 C24 C22 120.4(4) . . ? O3 C24 C22 121.6(4) . . ? O4 C24 Zn1 57.3(2) . 1_545 ? O3 C24 Zn1 60.7(2) . 1_545 ? C22 C24 Zn1 177.7(3) . 1_545 ? N3 C25 C26 124.8(8) . . ? N3 C25 H25 117.6 . . ? C26 C25 H25 117.6 . . ? C25 C26 C27 119.1(7) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 116.2(5) . . ? C28 C27 C30 122.6(5) . . ? C26 C27 C30 121.2(6) . . ? C27 C28 C29 119.9(7) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? N3 C29 C28 124.0(8) . . ? N3 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? C35 C30 C31 118.2(4) . . ? C35 C30 C27 120.3(5) . . ? C31 C30 C27 121.4(5) . . ? C32 C31 C30 121.0(5) . . ? C32 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? C33 C32 C31 120.5(5) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.1(5) . . ? C32 C33 H33 120.0 . . ? C34 C33 H33 120.0 . . ? C33 C34 C35 119.3(4) . . ? C33 C34 C36 122.1(4) . . ? C35 C34 C36 118.5(4) . . ? C30 C35 C34 121.0(4) . . ? C30 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? O6 C36 O5 123.6(4) . . ? O6 C36 C34 117.8(4) . . ? O5 C36 C34 118.5(4) . . ? N4 C37 C38 124.2(7) . . ? N4 C37 H37 117.9 . . ? C38 C37 H37 117.9 . . ? C39 C38 C37 118.4(7) . . ? C39 C38 H38 120.8 . . ? C37 C38 H38 120.8 . . ? C40 C39 C38 116.5(6) . . ? C40 C39 C42 121.6(5) . . ? C38 C39 C42 122.0(5) . . ? C41 C40 C39 120.4(6) . . ? C41 C40 H40 119.8 . . ? C39 C40 H40 119.8 . . ? N4 C41 C40 124.3(7) . . ? N4 C41 H41 117.8 . . ? C40 C41 H41 117.8 . . ? C47 C42 C43 118.5(5) . . ? C47 C42 C39 120.6(5) . . ? C43 C42 C39 120.9(4) . . ? C44 C43 C42 120.4(5) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C45 119.6(7) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? C46 C45 C44 120.8(6) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C45 C46 C47 119.2(6) . . ? C45 C46 C48 122.5(7) . . ? C47 C46 C48 118.3(7) . . ? C46 C47 C42 121.5(6) . . ? C46 C47 H47 119.3 . . ? C42 C47 H47 119.3 . . ? O8 C48 O7 120.5(16) . . ? O8 C48 O7' 123.5(18) . . ? O7 C48 O7' 27.4(11) . . ? O8 C48 O8' 21.1(15) . . ? O7 C48 O8' 120.6(16) . . ? O7' C48 O8' 134.7(18) . . ? O8 C48 C46 121.4(13) . . ? O7 C48 C46 118.1(12) . . ? O7' C48 C46 109.1(14) . . ? O8' C48 C46 116.2(13) . . ? N5 C49 C50 124.8(6) . . ? N5 C49 H49 117.6 . . ? C50 C49 H49 117.6 . . ? C51 C50 C49 121.0(6) . . ? C51 C50 H50 119.5 . . ? C49 C50 H50 119.5 . . ? C50 C51 C52 114.3(5) . . ? C50 C51 C54 121.4(5) . . ? C52 C51 C54 124.3(5) . . ? C51 C52 C53 121.2(7) . . ? C51 C52 H52 119.4 . . ? C53 C52 H52 119.4 . . ? N5 C53 C52 124.1(7) . . ? N5 C53 H53 117.9 . . ? C52 C53 H53 117.9 . . ? C55 C54 C59 120.0 . . ? C55 C54 C51 120.2(3) . . ? C59 C54 C51 119.8(3) . . ? C56 C55 C54 120.0 . . ? C56 C55 H55 120.0 . . ? C54 C55 H55 120.0 . . ? C55 C56 C57 120.0 . . ? C55 C56 C60 138.2(6) . . ? C57 C56 C60 101.7(6) . . ? C55 C56 C60' 103.9(7) . . ? C57 C56 C60' 136.0(7) . . ? C60 C56 C60' 34.8(8) . . ? C58 C57 C56 120.0 . . ? C58 C57 H57 120.0 . . ? C56 C57 H57 120.0 . . ? C57 C58 C59 120.0 . . ? C57 C58 H58 120.0 . . ? C59 C58 H58 120.0 . . ? C58 C59 C54 120.0 . . ? C58 C59 H59 120.0 . . ? C54 C59 H59 120.0 . . ? 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 O5 Zn1 O1 C12 -83.6(4) . . . . ? N2 Zn1 O1 C12 167.8(4) . . . . ? O4 Zn1 O1 C12 69.4(5) 1_565 . . . ? O3 Zn1 O1 C12 24.7(4) 1_565 . . . ? C24 Zn1 O1 C12 41.6(5) 1_565 . . . ? O6 Zn2 O2 C12 -141.4(4) 2_667 . . . ? O6 Zn2 O2 C12 38.6(4) . . . . ? O2 Zn2 O2 C12 123(4) 2_667 . . . ? O3 Zn2 O2 C12 -53.0(4) 1_565 . . . ? O3 Zn2 O2 C12 127.0(4) 2_657 . . . ? O1 Zn1 O5 C36 55.4(3) . . . . ? N2 Zn1 O5 C36 157.5(3) . . . . ? O4 Zn1 O5 C36 -108.0(3) 1_565 . . . ? O3 Zn1 O5 C36 -46.7(3) 1_565 . . . ? C24 Zn1 O5 C36 -77.5(3) 1_565 . . . ? O6 Zn2 O6 C36 173(7) 2_667 . . . ? O2 Zn2 O6 C36 -111.7(6) . . . . ? O2 Zn2 O6 C36 68.3(6) 2_667 . . . ? O3 Zn2 O6 C36 -22.1(6) 1_565 . . . ? O3 Zn2 O6 C36 157.9(6) 2_657 . . . ? O10' Zn3 O7 C48 -57.0(12) 1_655 . . . ? N5 Zn3 O7 C48 81.1(9) . . . . ? N1 Zn3 O7 C48 -172.5(8) . . . . ? O7' Zn3 O7 C48 -79(2) . . . . ? O9 Zn3 O7 C48 -73.2(9) 1_655 . . . ? O8 Zn3 O7 C48 9.5(9) . . . . ? O9' Zn3 O7 C48 -84.7(9) 1_655 . . . ? O8' Zn3 O7 C48 21.3(9) . . . . ? C60' Zn3 O7 C48 -73.5(13) 1_655 . . . ? O10' Zn3 O7' C48 -88.6(10) 1_655 . . . ? N5 Zn3 O7' C48 49.2(13) . . . . ? N1 Zn3 O7' C48 161.9(9) . . . . ? O7 Zn3 O7' C48 74(2) . . . . ? O9 Zn3 O7' C48 -101.0(10) 1_655 . . . ? O8 Zn3 O7' C48 -7.9(9) . . . . ? O9' Zn3 O7' C48 -112.6(11) 1_655 . . . ? O8' Zn3 O7' C48 3.3(9) . . . . ? C60' Zn3 O7' C48 -101.3(12) 1_655 . . . ? O10' Zn3 O8 C48 129.8(10) 1_655 . . . ? N5 Zn3 O8 C48 -133.8(10) . . . . ? N1 Zn3 O8 C48 -14.6(19) . . . . ? O7 Zn3 O8 C48 -10.1(9) . . . . ? O7' Zn3 O8 C48 8.5(10) . . . . ? O9 Zn3 O8 C48 100.0(11) 1_655 . . . ? O9' Zn3 O8 C48 71.3(11) 1_655 . . . ? O8' Zn3 O8 C48 -92(4) . . . . ? C60' Zn3 O8 C48 103.9(11) 1_655 . . . ? O10' Zn3 O8' C48 113.6(10) 1_655 . . . ? N5 Zn3 O8' C48 -151.7(10) . . . . ? N1 Zn3 O8' C48 -49.2(16) . . . . ? O7 Zn3 O8' C48 -21.3(9) . . . . ? O7' Zn3 O8' C48 -3.4(9) . . . . ? O9 Zn3 O8' C48 82.8(10) 1_655 . . . ? O8 Zn3 O8' C48 70(4) . . . . ? O9' Zn3 O8' C48 53.5(10) 1_655 . . . ? C60' Zn3 O8' C48 86.9(11) 1_655 . . . ? Zn3 O9 C60 O10 3.1(15) 1_455 . . . ? Zn3 O9 C60 C56 178.0(5) 1_455 . . . ? Zn3 O10' C60' O9' 6(3) 1_455 . . . ? Zn3 O10' C60' C56 -169(2) 1_455 . . . ? Zn3 O9' C60' O10' -4(2) 1_455 . . . ? Zn3 O9' C60' C56 171(3) 1_455 . . . ? O10' Zn3 N1 C5 50.7(5) 1_655 . . . ? N5 Zn3 N1 C5 -48.2(5) . . . . ? O7 Zn3 N1 C5 -169.2(6) . . . . ? O7' Zn3 N1 C5 175.0(7) . . . . ? O9 Zn3 N1 C5 80.4(5) 1_655 . . . ? O8 Zn3 N1 C5 -165.5(11) . . . . ? O9' Zn3 N1 C5 108.4(5) 1_655 . . . ? O8' Zn3 N1 C5 -146.2(9) . . . . ? C60' Zn3 N1 C5 75.7(6) 1_655 . . . ? O10' Zn3 N1 C1 -122.1(5) 1_655 . . . ? N5 Zn3 N1 C1 138.9(4) . . . . ? O7 Zn3 N1 C1 17.9(6) . . . . ? O7' Zn3 N1 C1 2.1(6) . . . . ? O9 Zn3 N1 C1 -92.5(4) 1_655 . . . ? O8 Zn3 N1 C1 21.7(12) . . . . ? O9' Zn3 N1 C1 -64.4(5) 1_655 . . . ? O8' Zn3 N1 C1 41.0(10) . . . . ? C60' Zn3 N1 C1 -97.1(6) 1_655 . . . ? O1 Zn1 N2 C17 -167.5(4) . . . . ? O5 Zn1 N2 C17 82.1(4) . . . . ? O4 Zn1 N2 C17 -24.2(4) 1_565 . . . ? O3 Zn1 N2 C17 -59.0(5) 1_565 . . . ? C24 Zn1 N2 C17 -37.5(4) 1_565 . . . ? O1 Zn1 N2 C13 16.9(4) . . . . ? O5 Zn1 N2 C13 -93.6(4) . . . . ? O4 Zn1 N2 C13 160.1(4) 1_565 . . . ? O3 Zn1 N2 C13 125.3(3) 1_565 . . . ? C24 Zn1 N2 C13 146.8(3) 1_565 . . . ? O10' Zn3 N5 C49 -18.4(6) 1_655 . . . ? N1 Zn3 N5 C49 85.9(5) . . . . ? O7 Zn3 N5 C49 -170.6(6) . . . . ? O7' Zn3 N5 C49 -163.1(8) . . . . ? O9 Zn3 N5 C49 -20.9(6) 1_655 . . . ? O8 Zn3 N5 C49 -117.8(7) . . . . ? O9' Zn3 N5 C49 -25.6(8) 1_655 . . . ? O8' Zn3 N5 C49 -124.3(7) . . . . ? C60' Zn3 N5 C49 -18.1(11) 1_655 . . . ? O10' Zn3 N5 C53 166.1(7) 1_655 . . . ? N1 Zn3 N5 C53 -89.6(6) . . . . ? O7 Zn3 N5 C53 13.9(7) . . . . ? O7' Zn3 N5 C53 21.4(9) . . . . ? O9 Zn3 N5 C53 163.6(6) 1_655 . . . ? O8 Zn3 N5 C53 66.8(8) . . . . ? O9' Zn3 N5 C53 158.9(7) 1_655 . . . ? O8' Zn3 N5 C53 60.2(8) . . . . ? C60' Zn3 N5 C53 166.5(11) 1_655 . . . ? C5 N1 C1 C2 -0.8(8) . . . . ? Zn3 N1 C1 C2 172.3(4) . . . . ? N1 C1 C2 C3 0.1(8) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C1 C2 C3 C6 -177.1(4) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C6 C3 C4 C5 177.2(5) . . . . ? C1 N1 C5 C4 1.0(9) . . . . ? Zn3 N1 C5 C4 -172.2(5) . . . . ? C3 C4 C5 N1 -0.4(9) . . . . ? C4 C3 C6 C7 148.1(5) . . . . ? C2 C3 C6 C7 -34.4(7) . . . . ? C4 C3 C6 C11 -35.4(7) . . . . ? C2 C3 C6 C11 142.1(5) . . . . ? C11 C6 C7 C8 -0.2(7) . . . . ? C3 C6 C7 C8 176.3(4) . . . . ? C6 C7 C8 C9 -1.8(8) . . . . ? C7 C8 C9 C10 1.5(8) . . . . ? C8 C9 C10 C11 0.8(7) . . . . ? C8 C9 C10 C12 -174.5(4) . . . . ? C9 C10 C11 C6 -2.8(6) . . . . ? C12 C10 C11 C6 172.6(4) . . . . ? C7 C6 C11 C10 2.5(6) . . . . ? C3 C6 C11 C10 -174.0(4) . . . . ? Zn2 O2 C12 O1 21.9(7) . . . . ? Zn2 O2 C12 C10 -155.0(3) . . . . ? Zn1 O1 C12 O2 -3.8(7) . . . . ? Zn1 O1 C12 C10 173.1(3) . . . . ? C11 C10 C12 O2 12.6(6) . . . . ? C9 C10 C12 O2 -172.1(4) . . . . ? C11 C10 C12 O1 -164.6(4) . . . . ? C9 C10 C12 O1 10.7(6) . . . . ? C17 N2 C13 C14 -1.9(7) . . . . ? Zn1 N2 C13 C14 173.9(4) . . . . ? N2 C13 C14 C15 -0.8(7) . . . . ? C13 C14 C15 C16 2.8(7) . . . . ? C13 C14 C15 C18 -174.0(4) . . . . ? C14 C15 C16 C17 -2.2(7) . . . . ? C18 C15 C16 C17 174.6(4) . . . . ? C13 N2 C17 C16 2.5(7) . . . . ? Zn1 N2 C17 C16 -173.3(4) . . . . ? C15 C16 C17 N2 -0.5(8) . . . . ? C16 C15 C18 C19 22.5(7) . . . . ? C14 C15 C18 C19 -160.9(5) . . . . ? C16 C15 C18 C23 -153.8(4) . . . . ? C14 C15 C18 C23 22.8(6) . . . . ? C23 C18 C19 C20 1.9(8) . . . . ? C15 C18 C19 C20 -174.5(5) . . . . ? C18 C19 C20 C21 1.0(9) . . . . ? C19 C20 C21 C22 -2.3(10) . . . . ? C20 C21 C22 C23 0.7(8) . . . . ? C20 C21 C22 C24 177.0(5) . . . . ? C21 C22 C23 C18 2.3(7) . . . . ? C24 C22 C23 C18 -174.0(4) . . . . ? C19 C18 C23 C22 -3.5(7) . . . . ? C15 C18 C23 C22 172.9(4) . . . . ? Zn1 O4 C24 O3 -0.3(5) 1_545 . . . ? Zn1 O4 C24 C22 179.6(4) 1_545 . . . ? Zn2 O3 C24 O4 -118.8(7) 1_545 . . . ? Zn1 O3 C24 O4 0.3(5) 1_545 . . . ? Zn2 O3 C24 C22 61.4(10) 1_545 . . . ? Zn1 O3 C24 C22 -179.6(4) 1_545 . . . ? Zn2 O3 C24 Zn1 -119.1(7) 1_545 . . 1_545 ? C23 C22 C24 O4 169.3(5) . . . . ? C21 C22 C24 O4 -6.9(8) . . . . ? C23 C22 C24 O3 -10.8(7) . . . . ? C21 C22 C24 O3 173.0(5) . . . . ? C23 C22 C24 Zn1 179(100) . . . 1_545 ? C21 C22 C24 Zn1 2(9) . . . 1_545 ? C29 N3 C25 C26 -0.1(12) . . . . ? N3 C25 C26 C27 0.2(11) . . . . ? C25 C26 C27 C28 0.0(8) . . . . ? C25 C26 C27 C30 179.8(5) . . . . ? C26 C27 C28 C29 -0.4(9) . . . . ? C30 C27 C28 C29 179.8(6) . . . . ? C25 N3 C29 C28 -0.3(12) . . . . ? C27 C28 C29 N3 0.6(12) . . . . ? C28 C27 C30 C35 -28.0(7) . . . . ? C26 C27 C30 C35 152.2(5) . . . . ? C28 C27 C30 C31 153.1(5) . . . . ? C26 C27 C30 C31 -26.7(7) . . . . ? C35 C30 C31 C32 1.5(7) . . . . ? C27 C30 C31 C32 -179.5(5) . . . . ? C30 C31 C32 C33 -0.7(8) . . . . ? C31 C32 C33 C34 -0.7(8) . . . . ? C32 C33 C34 C35 1.3(7) . . . . ? C32 C33 C34 C36 -175.8(4) . . . . ? C31 C30 C35 C34 -0.9(7) . . . . ? C27 C30 C35 C34 -179.9(4) . . . . ? C33 C34 C35 C30 -0.5(7) . . . . ? C36 C34 C35 C30 176.7(4) . . . . ? Zn2 O6 C36 O5 45.4(8) . . . . ? Zn2 O6 C36 C34 -136.4(5) . . . . ? Zn1 O5 C36 O6 2.0(6) . . . . ? Zn1 O5 C36 C34 -176.2(3) . . . . ? C33 C34 C36 O6 176.9(4) . . . . ? C35 C34 C36 O6 -0.2(6) . . . . ? C33 C34 C36 O5 -4.7(6) . . . . ? C35 C34 C36 O5 178.2(4) . . . . ? C41 N4 C37 C38 -1.9(12) . . . . ? N4 C37 C38 C39 0.3(12) . . . . ? C37 C38 C39 C40 1.7(9) . . . . ? C37 C38 C39 C42 -177.9(6) . . . . ? C38 C39 C40 C41 -2.1(9) . . . . ? C42 C39 C40 C41 177.5(5) . . . . ? C37 N4 C41 C40 1.5(11) . . . . ? C39 C40 C41 N4 0.5(11) . . . . ? C40 C39 C42 C47 -140.7(6) . . . . ? C38 C39 C42 C47 38.8(8) . . . . ? C40 C39 C42 C43 38.4(8) . . . . ? C38 C39 C42 C43 -142.1(6) . . . . ? C47 C42 C43 C44 -0.6(9) . . . . ? C39 C42 C43 C44 -179.7(6) . . . . ? C42 C43 C44 C45 -0.2(11) . . . . ? C43 C44 C45 C46 1.2(12) . . . . ? C44 C45 C46 C47 -1.4(11) . . . . ? C44 C45 C46 C48 178.2(7) . . . . ? C45 C46 C47 C42 0.5(10) . . . . ? C48 C46 C47 C42 -179.0(6) . . . . ? C43 C42 C47 C46 0.4(8) . . . . ? C39 C42 C47 C46 179.6(5) . . . . ? Zn3 O8 C48 O7 17.2(16) . . . . ? Zn3 O8 C48 O7' -15.1(17) . . . . ? Zn3 O8 C48 O8' 114(6) . . . . ? Zn3 O8 C48 C46 -164.7(8) . . . . ? Zn3 O7 C48 O8 -17.9(17) . . . . ? Zn3 O7 C48 O7' 87(4) . . . . ? Zn3 O7 C48 O8' -42.5(17) . . . . ? Zn3 O7 C48 C46 163.8(7) . . . . ? Zn3 O7' C48 O8 15.4(17) . . . . ? Zn3 O7' C48 O7 -77(4) . . . . ? Zn3 O7' C48 O8' -8(2) . . . . ? Zn3 O7' C48 C46 168.2(6) . . . . ? Zn3 O8' C48 O8 -59(5) . . . . ? Zn3 O8' C48 O7 37.2(14) . . . . ? Zn3 O8' C48 O7' 7(2) . . . . ? Zn3 O8' C48 C46 -168.6(8) . . . . ? C45 C46 C48 O8 171.7(14) . . . . ? C47 C46 C48 O8 -8.7(16) . . . . ? C45 C46 C48 O7 -10.1(14) . . . . ? C47 C46 C48 O7 169.5(11) . . . . ? C45 C46 C48 O7' 18.3(14) . . . . ? C47 C46 C48 O7' -162.2(12) . . . . ? C45 C46 C48 O8' -164.9(13) . . . . ? C47 C46 C48 O8' 14.7(15) . . . . ? C53 N5 C49 C50 2.5(11) . . . . ? Zn3 N5 C49 C50 -173.4(6) . . . . ? N5 C49 C50 C51 1.4(12) . . . . ? C49 C50 C51 C52 -4.0(10) . . . . ? C49 C50 C51 C54 175.1(6) . . . . ? C50 C51 C52 C53 3.0(12) . . . . ? C54 C51 C52 C53 -176.1(7) . . . . ? C49 N5 C53 C52 -3.5(13) . . . . ? Zn3 N5 C53 C52 172.2(7) . . . . ? C51 C52 C53 N5 0.8(15) . . . . ? C50 C51 C54 C55 -172.8(5) . . . . ? C52 C51 C54 C55 6.2(8) . . . . ? C50 C51 C54 C59 4.9(7) . . . . ? C52 C51 C54 C59 -176.1(6) . . . . ? C59 C54 C55 C56 0.0 . . . . ? C51 C54 C55 C56 177.7(4) . . . . ? C54 C55 C56 C57 0.0 . . . . ? C54 C55 C56 C60 -175.2(8) . . . . ? C54 C55 C56 C60' 177.7(14) . . . . ? O10 C60 C56 C55 162.6(9) . . . . ? O9 C60 C56 C55 -12.5(11) . . . . ? O10 C60 C56 C57 -13.1(13) . . . . ? O9 C60 C56 C57 171.8(6) . . . . ? O10 C60 C56 C60' 175(3) . . . . ? O9 C60 C56 C60' 0(2) . . . . ? O10' C60' C56 C55 -171(3) . . . . ? O9' C60' C56 C55 15(4) . . . . ? Zn3 C60' C56 C55 167(6) 1_455 . . . ? O10' C60' C56 C57 6(5) . . . . ? O9' C60' C56 C57 -167.7(19) . . . . ? Zn3 C60' C56 C57 -16(8) 1_455 . . . ? O10' C60' C56 C60 17.5(14) . . . . ? O9' C60' C56 C60 -156(5) . . . . ? Zn3 C60' C56 C60 -5(5) 1_455 . . . ? C55 C56 C57 C58 0.0 . . . . ? C60 C56 C57 C58 176.7(5) . . . . ? C60' C56 C57 C58 -176.8(19) . . . . ? C56 C57 C58 C59 0.0 . . . . ? C57 C58 C59 C54 0.0 . . . . ? C55 C54 C59 C58 0.0 . . . . ? C51 C54 C59 C58 -177.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.399 _refine_diff_density_min -1.345 _refine_diff_density_rms 0.084 data_2 _database_code_depnum_ccdc_archive 'CCDC 740527' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 N2 O5.5 Zn' _chemical_formula_weight 488.8042 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.623(3) _cell_length_b 19.684(5) _cell_length_c 10.774(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.452(4) _cell_angle_gamma 90.00 _cell_volume 2460.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7270 _exptl_absorpt_correction_T_max 0.7681 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13444 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4551 _reflns_number_gt 3039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1994)' _computing_structure_solution 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ; 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005) ; _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The bond lengths O5-H1W and O5-H2W were restrained to the target value of 0.82(2) \%A. Displacement parameters for O5, O6, O7, O8, C4, C5, C9, C10, C12, C21, and C22 with large Ueq values were also subjected to restraints. ; _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^)+(0.1755P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4551 _refine_ls_number_parameters 322 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.2455 _refine_ls_wR_factor_gt 0.2173 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.53746(5) 0.14894(3) 0.95608(6) 0.0620(3) Uani 1 1 d . . . N1 N 0.3913(4) 0.1283(2) 1.0483(4) 0.0623(11) Uani 1 1 d . . . N2 N 0.4398(4) -0.2498(2) 0.5405(4) 0.0618(11) Uani 1 1 d . . . O1 O 0.5074(4) 0.0938(2) 0.8074(4) 0.0738(10) Uani 1 1 d . . . O2 O 0.3804(4) 0.1736(2) 0.7584(4) 0.0934(14) Uani 1 1 d . . . O3 O -0.3505(3) 0.1011(2) 1.0669(4) 0.0749(11) Uani 1 1 d . . . O4 O -0.2378(4) 0.1445(3) 0.9291(5) 0.0980(16) Uani 1 1 d . . . O5 O 0.1419(14) 0.2052(7) 0.7601(15) 0.143(4) Uani 0.50 1 d PDU . . O6 O 0.8369(14) 0.2442(8) 0.7828(13) 0.171(5) Uani 0.50 1 d PU . . O7 O 0.041(3) 0.3082(14) 0.899(3) 0.149(9) Uani 0.25 1 d PU . . O8 O 0.971(3) 0.1847(17) 0.619(3) 0.166(11) Uani 0.25 1 d PU . . C1 C 0.4233(5) 0.1174(3) 0.7405(5) 0.0681(14) Uani 1 1 d . . . C2 C 0.3756(5) 0.0727(2) 0.6382(5) 0.0608(13) Uani 1 1 d . . . C3 C 0.2946(7) 0.0994(3) 0.5509(6) 0.097(2) Uani 1 1 d . . . H3 H 0.2736 0.1460 0.5534 0.117 Uiso 1 1 calc R . . C4 C 0.2455(9) 0.0571(4) 0.4611(7) 0.129(3) Uani 1 1 d U . . H4 H 0.1925 0.0752 0.3991 0.155 Uiso 1 1 calc R . . C5 C 0.2726(8) -0.0126(4) 0.4597(6) 0.113(3) Uani 1 1 d U . . H5 H 0.2337 -0.0421 0.4013 0.136 Uiso 1 1 calc R . . C6 C 0.3554(5) -0.0375(3) 0.5431(5) 0.0657(14) Uani 1 1 d . . . C7 C 0.4041(4) 0.0054(2) 0.6320(4) 0.0567(12) Uani 1 1 d . . . H7 H 0.4597 -0.0124 0.6916 0.068 Uiso 1 1 calc R . . C8 C 0.3839(5) -0.1108(3) 0.5407(5) 0.0578(12) Uani 1 1 d . . . C9 C 0.4450(8) -0.1420(3) 0.6354(7) 0.103(3) Uani 1 1 d U . . H9 H 0.4699 -0.1160 0.7063 0.124 Uiso 1 1 calc R . . C10 C 0.4721(7) -0.2093(3) 0.6326(7) 0.098(2) Uani 1 1 d U . . H10 H 0.5168 -0.2278 0.7011 0.117 Uiso 1 1 calc R . . C11 C 0.3511(6) -0.1521(3) 0.4452(6) 0.0771(18) Uani 1 1 d . . . H11 H 0.3084 -0.1340 0.3748 0.093 Uiso 1 1 calc R . . C12 C 0.3791(6) -0.2208(3) 0.4485(6) 0.0815(18) Uani 1 1 d U . . H12 H 0.3527 -0.2484 0.3802 0.098 Uiso 1 1 calc R . . C13 C -0.2512(5) 0.1113(3) 1.0252(6) 0.0730(16) Uani 1 1 d . . . C14 C -0.1512(4) 0.0765(3) 1.0938(5) 0.0607(12) Uani 1 1 d . . . C15 C -0.0408(4) 0.0959(3) 1.0725(5) 0.0609(13) Uani 1 1 d . . . H15 H -0.0290 0.1322 1.0167 0.073 Uiso 1 1 calc R . . C16 C 0.0541(4) 0.0636(3) 1.1306(4) 0.0555(11) Uani 1 1 d . . . C17 C 0.0352(5) 0.0084(3) 1.2059(5) 0.0763(16) Uani 1 1 d . . . H17 H 0.0988 -0.0157 1.2438 0.092 Uiso 1 1 calc R . . C18 C -0.0760(5) -0.0118(4) 1.2263(6) 0.093(2) Uani 1 1 d . . . H18 H -0.0878 -0.0495 1.2791 0.112 Uiso 1 1 calc R . . C19 C -0.1694(5) 0.0214(4) 1.1717(5) 0.0771(16) Uani 1 1 d . . . H19 H -0.2454 0.0072 1.1867 0.093 Uiso 1 1 calc R . . C20 C 0.1721(4) 0.0859(2) 1.1084(4) 0.0545(11) Uani 1 1 d . . . C21 C 0.1944(5) 0.1522(3) 1.0748(7) 0.0769(17) Uani 1 1 d U . . H21 H 0.1343 0.1850 1.0731 0.092 Uiso 1 1 calc R . . C22 C 0.3015(5) 0.1708(3) 1.0444(7) 0.0830(18) Uani 1 1 d U . . H22 H 0.3132 0.2163 1.0191 0.100 Uiso 1 1 calc R . . C23 C 0.3716(4) 0.0648(3) 1.0841(5) 0.0557(12) Uani 1 1 d . . . H23 H 0.4338 0.0334 1.0882 0.067 Uiso 1 1 calc R . . C24 C 0.2647(4) 0.0428(3) 1.1154(4) 0.0564(12) Uani 1 1 d . . . H24 H 0.2550 -0.0027 1.1421 0.068 Uiso 1 1 calc R . . H1W H 0.116(6) 0.205(3) 0.690(3) 0.085 Uiso 1 1 d D . . H2W H 0.128(6) 0.2425(18) 0.782(5) 0.085 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0370(4) 0.0561(4) 0.0921(6) 0.0022(3) -0.0023(3) -0.0033(2) N1 0.033(2) 0.064(2) 0.089(3) -0.003(2) -0.0035(19) 0.0041(19) N2 0.044(2) 0.058(2) 0.083(3) -0.001(2) -0.003(2) 0.0032(19) O1 0.059(2) 0.074(2) 0.088(3) -0.0050(19) -0.0020(19) -0.004(2) O2 0.096(4) 0.058(2) 0.124(4) -0.015(2) -0.019(3) -0.002(2) O3 0.030(2) 0.097(3) 0.097(3) 0.001(2) 0.0007(16) 0.0063(19) O4 0.051(3) 0.113(4) 0.129(4) 0.047(3) -0.002(3) 0.006(2) O5 0.120(8) 0.138(8) 0.174(9) 0.018(7) 0.013(7) 0.027(7) O6 0.166(9) 0.188(9) 0.162(8) 0.034(7) 0.035(7) -0.047(8) O7 0.154(13) 0.131(12) 0.162(12) -0.008(9) 0.019(9) -0.020(9) O8 0.162(14) 0.168(13) 0.168(13) -0.013(10) 0.004(10) 0.014(10) C1 0.061(4) 0.060(3) 0.083(4) 0.003(3) 0.006(3) -0.014(3) C2 0.065(4) 0.054(3) 0.063(3) 0.007(2) 0.005(2) -0.004(2) C3 0.143(7) 0.060(3) 0.084(4) 0.002(3) -0.030(4) 0.014(4) C4 0.190(7) 0.091(4) 0.098(5) -0.009(4) -0.069(5) 0.054(5) C5 0.161(7) 0.079(4) 0.092(4) -0.016(3) -0.053(4) 0.039(4) C6 0.081(4) 0.057(3) 0.058(3) 0.007(2) -0.007(3) 0.006(3) C7 0.049(3) 0.062(3) 0.060(3) 0.010(2) 0.005(2) 0.001(2) C8 0.060(3) 0.053(3) 0.061(3) 0.002(2) 0.000(2) 0.002(2) C9 0.141(6) 0.070(4) 0.092(4) -0.013(3) -0.046(4) 0.021(4) C10 0.124(6) 0.069(4) 0.095(4) 0.004(3) -0.036(4) 0.021(4) C11 0.072(4) 0.072(4) 0.084(4) -0.004(3) -0.023(3) 0.011(3) C12 0.075(4) 0.070(3) 0.095(4) -0.009(3) -0.029(3) 0.009(3) C13 0.033(3) 0.080(4) 0.105(5) -0.006(3) -0.002(3) 0.002(3) C14 0.031(3) 0.076(3) 0.075(3) -0.003(3) 0.001(2) 0.004(2) C15 0.035(3) 0.065(3) 0.083(3) 0.005(2) 0.006(2) 0.001(2) C16 0.032(3) 0.068(3) 0.066(3) 0.001(2) 0.0013(19) 0.000(2) C17 0.045(3) 0.104(4) 0.078(4) 0.027(3) -0.008(3) 0.001(3) C18 0.057(4) 0.125(5) 0.099(5) 0.052(4) 0.009(3) -0.005(4) C19 0.039(3) 0.111(5) 0.081(4) 0.020(3) 0.003(2) -0.010(3) C20 0.033(3) 0.059(3) 0.070(3) -0.001(2) -0.0062(19) -0.001(2) C21 0.038(3) 0.069(3) 0.124(5) -0.003(3) 0.004(3) 0.012(2) C22 0.049(3) 0.056(3) 0.144(5) 0.007(3) 0.008(3) 0.002(3) C23 0.035(3) 0.060(3) 0.071(3) 0.001(2) -0.001(2) 0.004(2) C24 0.038(3) 0.066(3) 0.065(3) 0.003(2) -0.002(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.955(4) 1_655 ? Zn1 O1 1.949(4) . ? Zn1 N2 2.011(4) 2_656 ? Zn1 N1 2.059(5) . ? N1 C22 1.336(7) . ? N1 C23 1.334(6) . ? N2 C10 1.311(8) . ? N2 C12 1.312(7) . ? N2 Zn1 2.011(4) 2_646 ? O1 C1 1.268(7) . ? O2 C1 1.233(8) . ? O3 C13 1.279(7) . ? O3 Zn1 1.955(4) 1_455 ? O4 C13 1.241(8) . ? O5 H1W 0.80(2) . ? O5 H2W 0.79(2) . ? C1 C2 1.491(8) . ? C2 C7 1.370(7) . ? C2 C3 1.393(8) . ? C3 C4 1.372(10) . ? C3 H3 0.9500 . ? C4 C5 1.409(10) . ? C4 H4 0.9500 . ? C5 C6 1.367(8) . ? C5 H5 0.9500 . ? C6 C7 1.373(7) . ? C6 C8 1.480(7) . ? C7 H7 0.9500 . ? C8 C11 1.348(8) . ? C8 C9 1.355(8) . ? C9 C10 1.362(8) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.393(8) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.503(7) . ? C14 C15 1.371(7) . ? C14 C19 1.396(8) . ? C15 C16 1.389(7) . ? C15 H15 0.9500 . ? C16 C17 1.382(7) . ? C16 C20 1.473(6) . ? C17 C18 1.383(8) . ? C17 H17 0.9500 . ? C18 C19 1.369(8) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C24 1.368(7) . ? C20 C21 1.384(8) . ? C21 C22 1.356(9) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.377(7) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 O3 Zn1 O1 108.25(18) 1_655 . ? O3 Zn1 N2 112.60(18) 1_655 2_656 ? O1 Zn1 N2 125.75(17) . 2_656 ? O3 Zn1 N1 98.57(17) 1_655 . ? O1 Zn1 N1 100.07(18) . . ? N2 Zn1 N1 107.31(18) 2_656 . ? C22 N1 C23 116.6(5) . . ? C22 N1 Zn1 121.9(4) . . ? C23 N1 Zn1 119.0(3) . . ? C10 N2 C12 115.1(5) . . ? C10 N2 Zn1 123.9(4) . 2_646 ? C12 N2 Zn1 120.6(4) . 2_646 ? C1 O1 Zn1 110.9(4) . . ? C13 O3 Zn1 106.9(4) . 1_455 ? H1W O5 H2W 102(3) . . ? O2 C1 O1 123.0(5) . . ? O2 C1 C2 120.6(5) . . ? O1 C1 C2 116.4(5) . . ? C7 C2 C3 119.2(5) . . ? C7 C2 C1 121.8(5) . . ? C3 C2 C1 118.9(5) . . ? C4 C3 C2 118.9(6) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.4(6) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 118.8(5) . . ? C5 C6 C8 119.2(5) . . ? C7 C6 C8 121.8(5) . . ? C2 C7 C6 122.5(5) . . ? C2 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C11 C8 C9 114.4(5) . . ? C11 C8 C6 123.2(5) . . ? C9 C8 C6 122.4(5) . . ? C10 C9 C8 122.4(6) . . ? C10 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? N2 C10 C9 123.6(6) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C8 C11 C12 120.8(5) . . ? C8 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? N2 C12 C11 123.8(6) . . ? N2 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? O4 C13 O3 122.5(5) . . ? O4 C13 C14 121.1(5) . . ? O3 C13 C14 116.3(6) . . ? C15 C14 C19 119.5(5) . . ? C15 C14 C13 119.7(5) . . ? C19 C14 C13 120.6(5) . . ? C14 C15 C16 121.6(5) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.3(5) . . ? C17 C16 C20 120.8(4) . . ? C15 C16 C20 120.9(5) . . ? C16 C17 C18 120.2(5) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 121.2(6) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C14 119.0(5) . . ? C18 C19 H19 120.5 . . ? C14 C19 H19 120.5 . . ? C24 C20 C21 116.1(5) . . ? C24 C20 C16 122.9(5) . . ? C21 C20 C16 120.9(5) . . ? C22 C21 C20 120.4(5) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? N1 C22 C21 123.5(6) . . ? N1 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? N1 C23 C24 122.6(5) . . ? N1 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C20 C24 C23 120.7(5) . . ? C20 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 N1 C22 150.7(5) 1_655 . . . ? O1 Zn1 N1 C22 -98.9(5) . . . . ? N2 Zn1 N1 C22 33.7(5) 2_656 . . . ? O3 Zn1 N1 C23 -47.7(4) 1_655 . . . ? O1 Zn1 N1 C23 62.7(4) . . . . ? N2 Zn1 N1 C23 -164.7(4) 2_656 . . . ? O3 Zn1 O1 C1 170.5(4) 1_655 . . . ? N2 Zn1 O1 C1 -52.1(4) 2_656 . . . ? N1 Zn1 O1 C1 67.9(4) . . . . ? Zn1 O1 C1 O2 11.0(7) . . . . ? Zn1 O1 C1 C2 -167.8(4) . . . . ? O2 C1 C2 C7 -165.8(6) . . . . ? O1 C1 C2 C7 13.0(8) . . . . ? O2 C1 C2 C3 10.3(9) . . . . ? O1 C1 C2 C3 -170.9(6) . . . . ? C7 C2 C3 C4 0.1(12) . . . . ? C1 C2 C3 C4 -176.1(8) . . . . ? C2 C3 C4 C5 2.6(15) . . . . ? C3 C4 C5 C6 -5.0(16) . . . . ? C4 C5 C6 C7 4.6(12) . . . . ? C4 C5 C6 C8 -179.7(8) . . . . ? C3 C2 C7 C6 -0.3(9) . . . . ? C1 C2 C7 C6 175.7(5) . . . . ? C5 C6 C7 C2 -2.1(10) . . . . ? C8 C6 C7 C2 -177.6(5) . . . . ? C5 C6 C8 C11 14.5(10) . . . . ? C7 C6 C8 C11 -170.0(6) . . . . ? C5 C6 C8 C9 -165.2(8) . . . . ? C7 C6 C8 C9 10.4(10) . . . . ? C11 C8 C9 C10 0.9(13) . . . . ? C6 C8 C9 C10 -179.4(8) . . . . ? C12 N2 C10 C9 0.5(12) . . . . ? Zn1 N2 C10 C9 -172.3(7) 2_646 . . . ? C8 C9 C10 N2 -1.5(15) . . . . ? C9 C8 C11 C12 0.5(11) . . . . ? C6 C8 C11 C12 -179.2(6) . . . . ? C10 N2 C12 C11 1.0(11) . . . . ? Zn1 N2 C12 C11 174.1(6) 2_646 . . . ? C8 C11 C12 N2 -1.5(12) . . . . ? Zn1 O3 C13 O4 -2.0(7) 1_455 . . . ? Zn1 O3 C13 C14 -177.6(4) 1_455 . . . ? O4 C13 C14 C15 18.1(9) . . . . ? O3 C13 C14 C15 -166.1(5) . . . . ? O4 C13 C14 C19 -157.0(6) . . . . ? O3 C13 C14 C19 18.7(8) . . . . ? C19 C14 C15 C16 -2.6(8) . . . . ? C13 C14 C15 C16 -177.8(5) . . . . ? C14 C15 C16 C17 3.6(8) . . . . ? C14 C15 C16 C20 -178.9(5) . . . . ? C15 C16 C17 C18 -2.7(9) . . . . ? C20 C16 C17 C18 179.8(6) . . . . ? C16 C17 C18 C19 0.8(11) . . . . ? C17 C18 C19 C14 0.3(11) . . . . ? C15 C14 C19 C18 0.6(9) . . . . ? C13 C14 C19 C18 175.7(6) . . . . ? C17 C16 C20 C24 26.5(8) . . . . ? C15 C16 C20 C24 -151.0(5) . . . . ? C17 C16 C20 C21 -155.7(6) . . . . ? C15 C16 C20 C21 26.8(8) . . . . ? C24 C20 C21 C22 3.6(9) . . . . ? C16 C20 C21 C22 -174.4(6) . . . . ? C23 N1 C22 C21 0.1(10) . . . . ? Zn1 N1 C22 C21 162.1(6) . . . . ? C20 C21 C22 N1 -2.1(12) . . . . ? C22 N1 C23 C24 0.3(8) . . . . ? Zn1 N1 C23 C24 -162.2(4) . . . . ? C21 C20 C24 C23 -3.2(7) . . . . ? C16 C20 C24 C23 174.7(5) . . . . ? N1 C23 C24 C20 1.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.885 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.099 data_3 _database_code_depnum_ccdc_archive 'CCDC 740528' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 N2 O4 Zn' _chemical_formula_weight 461.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.998(8) _cell_length_b 13.227(10) _cell_length_c 14.682(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.401(13) _cell_angle_gamma 90.00 _cell_volume 2132(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6683 _exptl_absorpt_correction_T_max 0.7561 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13395 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4835 _reflns_number_gt 4013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.6509P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4835 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.32034(2) 0.553448(19) 0.158433(17) 0.03571(11) Uani 1 1 d . . . N1 N 0.69130(19) 0.94400(14) -0.25011(14) 0.0396(4) Uani 1 1 d . . . N2 N 0.78189(18) 0.04276(15) 0.55069(14) 0.0407(4) Uani 1 1 d . . . O1 O 0.34290(15) 0.68811(12) 0.10655(12) 0.0450(4) Uani 1 1 d . . . O2 O 0.14414(16) 0.68710(16) 0.06653(14) 0.0573(5) Uani 1 1 d . . . O3 O 0.48995(15) 0.51447(13) 0.19228(12) 0.0458(4) Uani 1 1 d . . . O4 O 0.39373(17) 0.38892(15) 0.25616(15) 0.0613(5) Uani 1 1 d . . . C1 C 0.6506(2) 0.85487(18) -0.22152(17) 0.0459(6) Uani 1 1 d . . . H1 H 0.6892 0.7950 -0.2408 0.055 Uiso 1 1 calc R . . C2 C 0.5554(2) 0.84607(18) -0.16559(16) 0.0445(5) Uani 1 1 d . . . H2 H 0.5309 0.7811 -0.1461 0.053 Uiso 1 1 calc R . . C3 C 0.4947(2) 0.93172(17) -0.13730(15) 0.0369(5) Uani 1 1 d . . . C4 C 0.5387(2) 1.02439(19) -0.16670(18) 0.0457(6) Uani 1 1 d . . . H4 H 0.5017 1.0855 -0.1487 0.055 Uiso 1 1 calc R . . C5 C 0.6355(2) 1.02741(18) -0.22159(19) 0.0456(6) Uani 1 1 d . . . H5 H 0.6642 1.0915 -0.2402 0.055 Uiso 1 1 calc R . . C6 C 0.3869(2) 0.9227(2) -0.08204(17) 0.0428(5) Uani 1 1 d . . . C7 C 0.3691(2) 0.83655(17) -0.03009(15) 0.0367(5) Uani 1 1 d . . . H7 H 0.4306 0.7860 -0.0262 0.044 Uiso 1 1 calc R . . C8 C 0.2643(2) 0.82241(19) 0.01615(16) 0.0424(5) Uani 1 1 d . . . C9 C 0.1767(3) 0.8982(3) 0.0135(3) 0.0817(12) Uani 1 1 d . . . H9 H 0.1046 0.8898 0.0453 0.098 Uiso 1 1 calc R . . C10 C 0.1942(4) 0.9852(3) -0.0350(3) 0.1096(18) Uani 1 1 d . . . H10 H 0.1343 1.0370 -0.0362 0.132 Uiso 1 1 calc R . . C11 C 0.2985(3) 0.9984(3) -0.0823(3) 0.0812(12) Uani 1 1 d . . . H11 H 0.3099 1.0592 -0.1151 0.097 Uiso 1 1 calc R . . C12 C 0.2462(2) 0.72582(19) 0.06629(15) 0.0401(5) Uani 1 1 d . . . C13 C 0.6698(2) 0.0584(2) 0.5117(2) 0.0543(7) Uani 1 1 d . . . H13 H 0.6029 0.0244 0.5361 0.065 Uiso 1 1 calc R . . C14 C 0.6476(2) 0.1211(2) 0.4384(2) 0.0528(7) Uani 1 1 d . . . H14 H 0.5666 0.1305 0.4137 0.063 Uiso 1 1 calc R . . C15 C 0.7437(2) 0.17104(17) 0.40004(16) 0.0378(5) Uani 1 1 d . . . C16 C 0.85959(19) 0.15398(17) 0.44012(16) 0.0376(5) Uani 1 1 d . . . H16 H 0.9283 0.1860 0.4165 0.045 Uiso 1 1 calc R . . C17 C 0.8744(2) 0.09073(19) 0.51392(16) 0.0397(5) Uani 1 1 d . . . H17 H 0.9543 0.0804 0.5403 0.048 Uiso 1 1 calc R . . C18 C 0.7254(2) 0.24227(17) 0.32292(16) 0.0375(5) Uani 1 1 d . . . C19 C 0.6189(2) 0.29865(17) 0.31181(16) 0.0377(5) Uani 1 1 d . . . H19 H 0.5544 0.2868 0.3508 0.045 Uiso 1 1 calc R . . C20 C 0.6058(2) 0.37233(17) 0.24413(16) 0.0382(5) Uani 1 1 d . . . C21 C 0.6982(2) 0.3884(2) 0.18628(17) 0.0473(6) Uani 1 1 d . . . H21 H 0.6907 0.4403 0.1416 0.057 Uiso 1 1 calc R . . C22 C 0.8023(2) 0.3287(2) 0.19328(19) 0.0524(6) Uani 1 1 d . . . H22 H 0.8640 0.3375 0.1513 0.063 Uiso 1 1 calc R . . C23 C 0.8164(2) 0.2563(2) 0.26155(17) 0.0459(6) Uani 1 1 d . . . H23 H 0.8881 0.2161 0.2666 0.055 Uiso 1 1 calc R . . C24 C 0.4874(2) 0.42866(18) 0.23235(17) 0.0401(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.03337(16) 0.03530(16) 0.03916(17) 0.00125(10) 0.00809(11) 0.00081(10) N1 0.0407(10) 0.036(1) 0.0436(11) -0.0034(8) 0.0145(8) -0.0038(8) N2 0.0322(10) 0.0429(11) 0.0469(11) 0.0056(8) 0.0031(8) -0.0009(8) O1 0.0380(9) 0.0433(9) 0.0543(10) 0.0142(8) 0.0070(7) 0.0014(7) O2 0.0372(9) 0.0687(13) 0.0666(12) 0.0119(10) 0.0078(8) -0.0090(9) O3 0.0430(9) 0.0400(9) 0.0537(10) 0.0084(8) -0.0030(8) 0.0031(7) O4 0.0438(10) 0.0527(11) 0.0887(14) 0.0179(10) 0.0144(10) 0.0107(9) C1 0.0565(14) 0.0331(11) 0.0503(13) -0.005(1) 0.0223(11) 0.000(1) C2 0.0539(14) 0.0346(12) 0.0467(13) -0.0003(10) 0.0172(11) -0.005(1) C3 0.0362(11) 0.0416(12) 0.0336(11) 0.0023(9) 0.0069(9) 0.0012(9) C4 0.0466(14) 0.0371(12) 0.0551(15) 0.0035(11) 0.0171(11) 0.006(1) C5 0.0485(14) 0.0348(12) 0.0552(15) 0.0014(10) 0.0169(11) -0.003(1) C6 0.0382(12) 0.0487(13) 0.0424(13) 0.0106(10) 0.0104(10) 0.0058(10) C7 0.0332(11) 0.0384(11) 0.0391(11) 0.0037(9) 0.0067(9) 0.0045(9) C8 0.0358(11) 0.0519(14) 0.0402(12) 0.0117(10) 0.0086(9) 0.0055(10) C9 0.0533(17) 0.092(2) 0.105(3) 0.055(2) 0.0449(18) 0.0346(17) C10 0.078(2) 0.109(3) 0.148(4) 0.087(3) 0.069(3) 0.062(2) C11 0.068(2) 0.078(2) 0.103(3) 0.056(2) 0.0436(19) 0.0349(18) C12 0.0367(11) 0.0460(13) 0.0388(12) 0.0043(10) 0.0116(9) 0.0032(10) C13 0.0287(12) 0.0602(17) 0.0742(19) 0.0238(14) 0.0048(12) -0.0048(11) C14 0.0269(11) 0.0598(16) 0.0708(17) 0.0210(14) -0.0032(11) -0.0011(11) C15 0.0317(10) 0.0359(11) 0.0457(12) 0.0003(9) 0.0027(9) 0.0015(9) C16 0.0276(10) 0.0412(12) 0.0442(12) 0.0025(10) 0.0046(9) -0.0012(9) C17 0.0291(10) 0.0456(12) 0.0442(12) 0.0018(10) 0.0014(9) -0.0003(9) C18 0.0336(11) 0.0363(11) 0.0423(12) 0.0010(9) 0.0006(9) -0.0001(9) C19 0.0334(11) 0.0376(11) 0.0422(12) 0.0006(9) 0.0037(9) 0.0006(9) C20 0.0363(11) 0.0367(11) 0.0413(12) -0.0009(9) -0.0002(9) 0.0021(9) C21 0.0448(13) 0.0514(14) 0.0456(13) 0.0106(11) 0.0021(10) 0.0018(11) C22 0.0419(13) 0.0671(17) 0.0496(14) 0.0089(13) 0.0126(11) 0.0040(12) C23 0.0360(12) 0.0517(14) 0.0503(14) 0.0034(11) 0.0058(10) 0.0083(11) C24 0.0409(12) 0.0380(12) 0.0410(12) 0.0004(9) 0.0003(10) 0.0029(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 Zn1 O1 1.959(2) . ? Zn1 O3 1.970(2) . ? Zn1 N1 2.011(2) 4_576 ? Zn1 N2 2.055(2) 4_565 ? N1 C1 1.338(3) . ? N1 C5 1.342(3) . ? N1 Zn1 2.011(2) 4_675 ? N2 C17 1.339(3) . ? N2 C13 1.344(3) . ? N2 Zn1 2.055(2) 4_666 ? O1 C12 1.286(3) . ? O2 C12 1.234(3) . ? O3 C24 1.279(3) . ? O4 C24 1.226(3) . ? C1 C2 1.373(3) . ? C1 H1 0.9500 . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 C6 1.480(3) . ? C4 C5 1.373(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.392(3) . ? C6 C11 1.395(4) . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C9 1.389(4) . ? C8 C12 1.494(3) . ? C9 C10 1.374(5) . ? C9 H9 0.9500 . ? C10 C11 1.387(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 C14 1.369(4) . ? C13 H13 0.9500 . ? C14 C15 1.394(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 C18 1.478(3) . ? C16 C17 1.371(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.390(3) . ? C18 C23 1.398(3) . ? C19 C20 1.393(3) . ? C19 H19 0.9500 . ? C20 C21 1.379(3) . ? C20 C24 1.501(3) . ? C21 C22 1.389(4) . ? C21 H21 0.9500 . ? C22 C23 1.389(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 101.31(7) . . ? O1 Zn1 N1 110.80(8) . 4_576 ? O3 Zn1 N1 122.07(9) . 4_576 ? O1 Zn1 N2 106.79(9) . 4_565 ? O3 Zn1 N2 100.41(8) . 4_565 ? N1 Zn1 N2 113.78(9) 4_576 4_565 ? C1 N1 C5 117.3(2) . . ? C1 N1 Zn1 119.15(15) . 4_675 ? C5 N1 Zn1 123.29(16) . 4_675 ? C17 N2 C13 117.1(2) . . ? C17 N2 Zn1 118.50(16) . 4_666 ? C13 N2 Zn1 124.38(17) . 4_666 ? C12 O1 Zn1 114.28(15) . . ? C24 O3 Zn1 107.59(15) . . ? N1 C1 C2 123.0(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 116.2(2) . . ? C2 C3 C6 120.8(2) . . ? C4 C3 C6 122.9(2) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N1 C5 C4 123.0(2) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C7 C6 C11 117.9(2) . . ? C7 C6 C3 120.6(2) . . ? C11 C6 C3 121.4(2) . . ? C8 C7 C6 121.8(2) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 119.0(2) . . ? C7 C8 C12 119.7(2) . . ? C9 C8 C12 121.2(2) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.7(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C6 120.4(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? O2 C12 O1 124.4(2) . . ? O2 C12 C8 120.3(2) . . ? O1 C12 C8 115.3(2) . . ? N2 C13 C14 123.0(2) . . ? N2 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 116.8(2) . . ? C16 C15 C18 120.5(2) . . ? C14 C15 C18 122.7(2) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N2 C17 C16 123.4(2) . . ? N2 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C19 C18 C23 118.9(2) . . ? C19 C18 C15 120.5(2) . . ? C23 C18 C15 120.5(2) . . ? C18 C19 C20 120.7(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.9(2) . . ? C21 C20 C24 121.2(2) . . ? C19 C20 C24 118.8(2) . . ? C20 C21 C22 120.1(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C18 120.2(2) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? O4 C24 O3 123.6(2) . . ? O4 C24 C20 119.5(2) . . ? O3 C24 C20 116.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C12 170.34(16) . . . . ? N1 Zn1 O1 C12 -58.72(19) 4_576 . . . ? N2 Zn1 O1 C12 65.69(18) 4_565 . . . ? O1 Zn1 O3 C24 176.40(16) . . . . ? N1 Zn1 O3 C24 52.84(18) 4_576 . . . ? N2 Zn1 O3 C24 -73.95(18) 4_565 . . . ? C5 N1 C1 C2 0.3(4) . . . . ? Zn1 N1 C1 C2 -174.1(2) 4_675 . . . ? N1 C1 C2 C3 1.3(4) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C1 C2 C3 C6 175.9(2) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C6 C3 C4 C5 -176.8(2) . . . . ? C1 N1 C5 C4 -1.2(4) . . . . ? Zn1 N1 C5 C4 172.9(2) 4_675 . . . ? C3 C4 C5 N1 0.6(4) . . . . ? C2 C3 C6 C7 23.3(4) . . . . ? C4 C3 C6 C7 -159.0(2) . . . . ? C2 C3 C6 C11 -154.8(3) . . . . ? C4 C3 C6 C11 22.9(4) . . . . ? C11 C6 C7 C8 3.6(4) . . . . ? C3 C6 C7 C8 -174.5(2) . . . . ? C6 C7 C8 C9 -2.6(4) . . . . ? C6 C7 C8 C12 176.3(2) . . . . ? C7 C8 C9 C10 0.5(6) . . . . ? C12 C8 C9 C10 -178.4(4) . . . . ? C8 C9 C10 C11 0.5(8) . . . . ? C9 C10 C11 C6 0.6(8) . . . . ? C7 C6 C11 C10 -2.6(6) . . . . ? C3 C6 C11 C10 175.5(4) . . . . ? Zn1 O1 C12 O2 6.7(3) . . . . ? Zn1 O1 C12 C8 -172.66(16) . . . . ? C7 C8 C12 O2 -142.1(3) . . . . ? C9 C8 C12 O2 36.8(4) . . . . ? C7 C8 C12 O1 37.3(3) . . . . ? C9 C8 C12 O1 -143.8(3) . . . . ? C17 N2 C13 C14 -0.9(4) . . . . ? Zn1 N2 C13 C14 -178.2(2) 4_666 . . . ? N2 C13 C14 C15 0.9(5) . . . . ? C13 C14 C15 C16 -0.3(4) . . . . ? C13 C14 C15 C18 -177.9(3) . . . . ? C14 C15 C16 C17 -0.2(4) . . . . ? C18 C15 C16 C17 177.4(2) . . . . ? C13 N2 C17 C16 0.3(4) . . . . ? Zn1 N2 C17 C16 177.83(18) 4_666 . . . ? C15 C16 C17 N2 0.2(4) . . . . ? C16 C15 C18 C19 -147.2(2) . . . . ? C14 C15 C18 C19 30.3(4) . . . . ? C16 C15 C18 C23 30.8(3) . . . . ? C14 C15 C18 C23 -151.7(3) . . . . ? C23 C18 C19 C20 -3.8(3) . . . . ? C15 C18 C19 C20 174.2(2) . . . . ? C18 C19 C20 C21 1.3(3) . . . . ? C18 C19 C20 C24 177.7(2) . . . . ? C19 C20 C21 C22 2.4(4) . . . . ? C24 C20 C21 C22 -174.0(2) . . . . ? C20 C21 C22 C23 -3.3(4) . . . . ? C21 C22 C23 C18 0.7(4) . . . . ? C19 C18 C23 C22 2.9(4) . . . . ? C15 C18 C23 C22 -175.2(2) . . . . ? Zn1 O3 C24 O4 -10.1(3) . . . . ? Zn1 O3 C24 C20 165.66(16) . . . . ? C21 C20 C24 O4 150.7(3) . . . . ? C19 C20 C24 O4 -25.7(3) . . . . ? C21 C20 C24 O3 -25.2(3) . . . . ? C19 C20 C24 O3 158.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.916 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.069 data_4 _database_code_depnum_ccdc_archive 'CCDC 740529' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H26 N2 O8 Zn2' _chemical_formula_sum 'C31 H26 N2 O8 Zn2' _chemical_formula_weight 685.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.482(2) _cell_length_b 8.7429(11) _cell_length_c 20.933(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.531(2) _cell_angle_gamma 90.00 _cell_volume 2786.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6265 _exptl_absorpt_correction_T_max 0.6647 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7588 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3752 _reflns_number_gt 3296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Siemens, 1996)' _computing_cell_refinement 'Bruker SMART (Siemens, 1996)' _computing_data_reduction 'Bruker SAINT (Siemens, 1994)' _computing_structure_solution 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ; 'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005) ; _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All C-C bond lengths in the pimelic acid molecule were restrained to the target value of 1.53(2) \%A. Atoms O6 and O8 are disordered over two positions and bond lengths C25-O6 and C31-O8 were restrained to a target value of 1.23(2) \%A. Displacement parameters for disordered O atoms and atoms O5, O7, C26, C27, C29, C30 with large Ueq values were also subjected to restraints. ; _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^)+(0.0368P)^2^+3.7434P] 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 0.18(3) _refine_ls_number_reflns 3752 _refine_ls_number_parameters 411 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.18576(3) 0.39958(11) 0.91159(2) 0.0386(3) Uani 1 1 d . . . Zn2 Zn 0.42699(3) 0.39912(12) 1.00971(2) 0.0390(3) Uani 1 1 d . . . N1 N 0.0729(5) 0.5111(9) 0.8502(3) 0.0346(16) Uani 1 1 d . . . N2 N 0.0370(5) 0.9894(10) 0.5689(3) 0.0429(19) Uani 1 1 d . . . O1 O 0.2571(5) 0.4999(10) 0.8699(3) 0.061(2) Uani 1 1 d . . . O2 O 0.4048(5) 0.4845(9) 0.9186(3) 0.057(2) Uani 1 1 d . . . O3 O 0.2050(4) 0.4861(8) 1.0041(3) 0.0473(17) Uani 1 1 d . . . O4 O 0.3488(5) 0.4991(10) 1.0499(3) 0.065(2) Uani 1 1 d . . . O5 O 0.4396(7) 0.1869(8) 0.9928(4) 0.064(2) Uani 1 1 d U . . O6 O 0.4672(7) 0.1630(13) 1.1010(4) 0.071(4) Uani 0.84(3) 1 d PDU . . O7 O 0.1721(7) 0.1836(9) 0.9305(4) 0.071(3) Uani 1 1 d U A . O8 O 0.1463(7) 0.1662(13) 0.8171(5) 0.063(4) Uani 0.80(3) 1 d PDU A 1 C1 C 0.0551(6) 0.5186(12) 0.7846(4) 0.045(3) Uani 1 1 d . . . H1 H 0.0942 0.4708 0.7672 0.054 Uiso 1 1 calc R . . C2 C -0.0167(7) 0.5913(11) 0.7390(4) 0.044(3) Uani 1 1 d . . . H2 H -0.0262 0.5949 0.6913 0.052 Uiso 1 1 calc R . . C3 C -0.0788(6) 0.6635(12) 0.7634(4) 0.034(2) Uani 1 1 d . . . C4 C -0.0541(7) 0.6527(13) 0.8346(5) 0.045(2) Uani 1 1 d . . . H4 H -0.0902 0.6984 0.8554 0.054 Uiso 1 1 calc R . . C5 C 0.0179(7) 0.5810(13) 0.8741(5) 0.048(3) Uani 1 1 d . . . H5 H 0.0317 0.5786 0.9225 0.058 Uiso 1 1 calc R . . C6 C -0.1544(6) 0.7409(11) 0.7171(4) 0.036(2) Uani 1 1 d . . . C7 C -0.2367(6) 0.7328(12) 0.7253(5) 0.041(2) Uani 1 1 d . . . H7 H -0.2411 0.6806 0.7637 0.049 Uiso 1 1 calc R . . C8 C -0.3073(7) 0.7997(12) 0.6782(6) 0.052(3) Uani 1 1 d . . . H8 H -0.3610 0.7922 0.6850 0.062 Uiso 1 1 calc R . . C9 C -0.3088(6) 0.8808(11) 0.6192(6) 0.040(2) Uani 1 1 d . . . H9 H -0.3613 0.9254 0.5875 0.048 Uiso 1 1 calc R . . C10 C -0.2285(5) 0.8923(10) 0.6098(5) 0.035(2) Uani 1 1 d . . . C11 C -0.1537(6) 0.8230(10) 0.6577(4) 0.037(2) Uani 1 1 d . . . H11 H -0.1000 0.8304 0.6509 0.044 Uiso 1 1 calc R . . C12 C 0.2757(6) 0.5268(11) 1.0519(5) 0.041(2) Uani 1 1 d . . . C13 C 0.0914(7) 0.9228(12) 0.5449(5) 0.042(2) Uani 1 1 d . . . H13 H 0.0786 0.9274 0.4967 0.051 Uiso 1 1 calc R . . C14 C 0.1688(7) 0.8440(13) 0.5885(5) 0.043(2) Uani 1 1 d . . . H14 H 0.2077 0.7987 0.5703 0.052 Uiso 1 1 calc R . . C15 C 0.1851(6) 0.8361(12) 0.6592(4) 0.037(2) Uani 1 1 d . . . C16 C 0.1307(7) 0.9037(10) 0.6829(4) 0.044(3) Uani 1 1 d . . . H16 H 0.1424 0.8992 0.7309 0.053 Uiso 1 1 calc R . . C17 C 0.0576(6) 0.9804(11) 0.6396(4) 0.043(2) Uani 1 1 d . . . H17 H 0.0201 1.0286 0.6585 0.052 Uiso 1 1 calc R . . C18 C 0.2688(6) 0.7573(11) 0.7092(4) 0.036(2) Uani 1 1 d . . . C19 C 0.3439(7) 0.7626(12) 0.6981(5) 0.048(3) Uani 1 1 d . . . H19 H 0.3443 0.8125 0.6579 0.057 Uiso 1 1 calc R . . C20 C 0.4225(6) 0.6954(13) 0.7450(5) 0.049(3) Uani 1 1 d . . . H20 H 0.4763 0.7006 0.7382 0.059 Uiso 1 1 calc R . . C21 C 0.4159(7) 0.6231(12) 0.8002(7) 0.052(3) Uani 1 1 d . . . H21 H 0.4674 0.5795 0.8338 0.063 Uiso 1 1 calc R . . C22 C 0.3398(7) 0.6101(10) 0.8098(5) 0.041(2) Uani 1 1 d . . . C23 C 0.2652(6) 0.6800(10) 0.7629(5) 0.038(2) Uani 1 1 d . . . H23 H 0.2111 0.6728 0.7691 0.045 Uiso 1 1 calc R . . C24 C 0.3332(6) 0.5229(11) 0.8723(4) 0.040(2) Uani 1 1 d . . . C25 C 0.4474(7) 0.1085(10) 1.0422(5) 0.043(3) Uani 1 1 d D . . C26 C 0.4471(9) -0.0606(13) 1.0428(5) 0.076(3) Uani 1 1 d DU . . H26A H 0.5084 -0.0968 1.0574 0.091 Uiso 1 1 calc R . . H26B H 0.4247 -0.0953 1.0781 0.091 Uiso 1 1 calc R . . C27 C 0.3967(8) -0.1306(14) 0.9795(6) 0.100(4) Uani 1 1 d DU . . H27A H 0.3835 -0.2335 0.9927 0.120 Uiso 1 1 calc R . . H27B H 0.4390 -0.1476 0.9570 0.120 Uiso 1 1 calc R . . C28 C 0.3169(4) -0.0855(6) 0.9236(3) 0.0688(17) Uani 1 1 d D . . H28A H 0.3101 -0.1425 0.8810 0.083 Uiso 1 1 calc R . . H28B H 0.3182 0.0253 0.9143 0.083 Uiso 1 1 calc R . . C29 C 0.2354(8) -0.1250(14) 0.9477(6) 0.100(4) Uani 1 1 d DU . . H29A H 0.2295 -0.2364 0.9530 0.121 Uiso 1 1 calc R . . H29B H 0.2423 -0.0726 0.9914 0.121 Uiso 1 1 calc R . . C30 C 0.1583(8) -0.0615(12) 0.8869(5) 0.069(3) Uani 1 1 d DU A . H30A H 0.1035 -0.0867 0.8936 0.083 Uiso 1 1 calc R . . H30B H 0.1559 -0.1142 0.8443 0.083 Uiso 1 1 calc R . . C31 C 0.1600(8) 0.1099(11) 0.8755(6) 0.056(3) Uani 1 1 d D . . O8' O 0.2155(8) 0.2037(11) 0.8636(7) 0.084(5) Uani 0.452(17) 1 d PDU A . O6' O 0.4924(14) 0.172(3) 1.0118(13) 0.032(8) Uani 0.131(14) 1 d PDU . . 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 0.0415(6) 0.0351(6) 0.0318(5) 0.0042(5) 0.0059(5) -0.0046(5) Zn2 0.0417(6) 0.0367(7) 0.0320(5) -0.0037(5) 0.0069(5) 0.0044(5) N1 0.042(4) 0.031(4) 0.031(4) -0.003(3) 0.014(3) -0.001(3) N2 0.045(5) 0.048(5) 0.025(4) 0.010(3) 0.002(3) -0.005(4) O1 0.048(4) 0.086(6) 0.049(4) 0.017(4) 0.017(3) -0.009(4) O2 0.062(4) 0.057(5) 0.044(4) 0.008(3) 0.012(4) 0.021(3) O3 0.042(4) 0.061(5) 0.031(3) -0.009(3) 0.005(3) -0.009(3) O4 0.049(4) 0.095(6) 0.047(4) -0.038(4) 0.015(3) -0.007(4) O5 0.093(6) 0.039(4) 0.052(4) 0.001(3) 0.018(4) 0.006(3) O6 0.093(7) 0.077(6) 0.049(5) -0.012(4) 0.034(4) -0.018(5) O7 0.126(6) 0.046(4) 0.051(4) 0.003(3) 0.046(4) 0.008(4) O8 0.074(6) 0.072(6) 0.048(5) 0.018(4) 0.029(4) 0.005(4) C1 0.036(5) 0.057(6) 0.038(5) 0.010(4) 0.009(4) 0.014(4) C2 0.048(6) 0.062(7) 0.029(5) -0.004(4) 0.024(4) 0.006(4) C3 0.037(5) 0.036(5) 0.034(4) -0.003(4) 0.020(4) -0.005(4) C4 0.056(6) 0.049(6) 0.035(5) 0.001(4) 0.024(5) 0.005(5) C5 0.062(7) 0.052(6) 0.027(5) -0.004(4) 0.014(5) -0.005(5) C6 0.048(5) 0.035(5) 0.025(4) 0.004(3) 0.015(3) -0.003(4) C7 0.034(5) 0.049(6) 0.047(5) 0.006(4) 0.024(4) -0.010(4) C8 0.048(6) 0.052(7) 0.068(7) 0.006(5) 0.037(5) 0.000(4) C9 0.025(5) 0.049(6) 0.044(5) -0.001(4) 0.012(4) -0.004(4) C10 0.020(4) 0.042(5) 0.039(5) -0.003(4) 0.007(4) 0.003(3) C11 0.041(5) 0.045(6) 0.028(4) 0.008(4) 0.017(4) -0.007(4) C12 0.043(5) 0.038(5) 0.045(5) -0.001(4) 0.018(4) -0.008(4) C13 0.052(6) 0.048(6) 0.029(5) 0.010(4) 0.019(4) 0.009(4) C14 0.045(5) 0.053(6) 0.031(5) 0.005(4) 0.014(4) 0.007(5) C15 0.039(5) 0.035(5) 0.032(4) 0.006(4) 0.008(4) -0.003(4) C16 0.044(6) 0.051(6) 0.025(4) 0.010(4) 0.001(4) 0.006(4) C17 0.056(6) 0.049(6) 0.028(4) -0.009(4) 0.020(4) -0.005(4) C18 0.026(4) 0.044(5) 0.035(4) -0.004(4) 0.007(3) -0.002(4) C19 0.060(7) 0.045(6) 0.043(5) 0.003(4) 0.026(5) -0.001(5) C20 0.026(5) 0.060(7) 0.059(6) 0.003(5) 0.014(4) -0.001(4) C21 0.043(6) 0.050(6) 0.056(7) 0.006(5) 0.010(5) 0.010(5) C22 0.057(6) 0.036(5) 0.029(4) 0.003(3) 0.013(4) -0.005(4) C23 0.027(4) 0.044(6) 0.038(5) -0.001(4) 0.008(4) 0.004(4) C24 0.051(6) 0.039(5) 0.022(4) 0.004(4) 0.005(4) -0.004(4) C25 0.055(6) 0.041(6) 0.042(5) -0.004(4) 0.028(5) 0.001(4) C26 0.117(7) 0.050(5) 0.046(4) 0.011(4) 0.015(4) -0.011(5) C27 0.105(6) 0.044(5) 0.103(7) 0.012(4) -0.015(5) -0.003(4) C28 0.078(4) 0.038(3) 0.082(4) -0.004(3) 0.021(4) 0.003(3) C29 0.157(9) 0.048(5) 0.067(5) 0.009(4) 0.009(6) 0.028(5) C30 0.091(6) 0.042(5) 0.053(5) -0.012(4) 0.004(4) -0.013(4) C31 0.064(7) 0.051(7) 0.054(7) 0.006(5) 0.024(6) 0.012(5) O8' 0.100(9) 0.068(6) 0.110(8) -0.003(5) 0.070(7) -0.010(5) O6' 0.006(10) 0.037(10) 0.049(12) 0.003(7) 0.007(7) 0.007(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.924(7) . ? Zn1 O7 1.960(8) . ? Zn1 O3 1.988(6) . ? Zn1 N1 2.057(7) . ? Zn1 O8' 2.136(10) . ? Zn2 O5 1.915(7) . ? Zn2 O2 1.948(7) . ? Zn2 O4 1.991(8) . ? Zn2 N2 2.013(8) 4_565 ? Zn2 O6' 2.25(2) . ? N1 C1 1.291(11) . ? N1 C5 1.340(14) . ? N2 C13 1.317(14) . ? N2 C17 1.388(10) . ? N2 Zn2 2.013(7) 4_464 ? O1 C24 1.251(12) . ? O2 C24 1.253(10) . ? O3 C12 1.261(10) . ? O4 C12 1.246(12) . ? O5 C25 1.205(12) . ? O6 C25 1.240(11) . ? O7 C31 1.269(13) . ? O8 C31 1.254(11) . ? C1 C2 1.360(13) . ? C1 H1 0.9500 . ? C2 C3 1.452(13) . ? C2 H2 0.9500 . ? C3 C4 1.391(12) . ? C3 C6 1.423(12) . ? C4 C5 1.316(15) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.432(14) . ? C6 C11 1.440(12) . ? C7 C8 1.337(14) . ? C7 H7 0.9500 . ? C8 C9 1.416(15) . ? C8 H8 0.9500 . ? C9 C10 1.414(13) . ? C9 H9 0.9500 . ? C10 C11 1.395(12) . ? C10 C12 1.428(13) 4_464 ? C11 H11 0.9500 . ? C12 C10 1.428(13) 4_565 ? C13 C14 1.430(14) . ? C13 H13 0.9500 . ? C14 C15 1.399(13) . ? C14 H14 0.9500 . ? C15 C16 1.319(14) . ? C15 C18 1.539(12) . ? C16 C17 1.374(13) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.334(13) . ? C18 C19 1.345(15) . ? C19 C20 1.419(14) . ? C19 H19 0.9500 . ? C20 C21 1.358(16) . ? C20 H20 0.9500 . ? C21 C22 1.350(16) . ? C21 H21 0.9500 . ? C22 C23 1.387(13) . ? C22 C24 1.553(12) . ? C23 H23 0.9500 . ? C25 O6' 1.276(17) . ? C25 C26 1.479(11) . ? C26 C27 1.407(11) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.44(1) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.642(13) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.518(11) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.519(11) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O8' 1.322(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O7 132.0(4) . . ? O1 Zn1 O3 111.8(3) . . ? O7 Zn1 O3 99.0(3) . . ? O1 Zn1 N1 93.7(3) . . ? O7 Zn1 N1 115.9(4) . . ? O3 Zn1 N1 101.4(3) . . ? O1 Zn1 O8' 82.0(4) . . ? O7 Zn1 O8' 52.3(4) . . ? O3 Zn1 O8' 141.6(4) . . ? N1 Zn1 O8' 113.7(4) . . ? O5 Zn2 O2 100.6(3) . . ? O5 Zn2 O4 129.5(4) . . ? O2 Zn2 O4 109.6(3) . . ? O5 Zn2 N2 116.6(4) . 4_565 ? O2 Zn2 N2 101.8(3) . 4_565 ? O4 Zn2 N2 96.0(3) . 4_565 ? O5 Zn2 O6' 20.6(6) . . ? O2 Zn2 O6' 105.4(6) . . ? O4 Zn2 O6' 139.6(5) . . ? N2 Zn2 O6' 95.9(6) 4_565 . ? C1 N1 C5 117.6(8) . . ? C1 N1 Zn1 118.2(6) . . ? C5 N1 Zn1 124.2(6) . . ? C13 N2 C17 117.2(7) . . ? C13 N2 Zn2 124.3(6) . 4_464 ? C17 N2 Zn2 118.5(7) . 4_464 ? C24 O1 Zn1 146.3(6) . . ? C24 O2 Zn2 129.0(7) . . ? C12 O3 Zn1 129.4(6) . . ? C12 O4 Zn2 153.0(6) . . ? C25 O5 Zn2 112.1(6) . . ? C31 O7 Zn1 107.2(6) . . ? N1 C1 C2 123.5(9) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 119.8(8) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C6 125.6(9) . . ? C4 C3 C2 113.1(8) . . ? C6 C3 C2 121.3(8) . . ? C5 C4 C3 121.9(11) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 N1 124.0(9) . . ? C4 C5 H5 118.0 . . ? N1 C5 H5 118.0 . . ? C3 C6 C7 121.2(8) . . ? C3 C6 C11 122.0(9) . . ? C7 C6 C11 116.7(8) . . ? C8 C7 C6 119.1(9) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 125.6(10) . . ? C7 C8 H8 117.2 . . ? C9 C8 H8 117.2 . . ? C10 C9 C8 116.9(9) . . ? C10 C9 H9 121.6 . . ? C8 C9 H9 121.6 . . ? C11 C10 C9 119.1(9) . . ? C11 C10 C12 120.5(8) . 4_464 ? C9 C10 C12 120.4(8) . 4_464 ? C10 C11 C6 122.6(9) . . ? C10 C11 H11 118.7 . . ? C6 C11 H11 118.7 . . ? O4 C12 O3 122.0(9) . . ? O4 C12 C10 119.2(8) . 4_565 ? O3 C12 C10 118.9(8) . 4_565 ? N2 C13 C14 122.7(9) . . ? N2 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 117.5(10) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C16 C15 C14 119.5(9) . . ? C16 C15 C18 120.4(8) . . ? C14 C15 C18 120.0(9) . . ? C15 C16 C17 121.4(9) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 N2 121.7(9) . . ? C16 C17 H17 119.2 . . ? N2 C17 H17 119.2 . . ? C23 C18 C19 120.3(9) . . ? C23 C18 C15 118.8(9) . . ? C19 C18 C15 120.8(9) . . ? C18 C19 C20 121.5(10) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C21 C20 C19 115.6(10) . . ? C21 C20 H20 122.2 . . ? C19 C20 H20 122.2 . . ? C22 C21 C20 123.3(10) . . ? C22 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? C21 C22 C23 118.7(9) . . ? C21 C22 C24 122.4(9) . . ? C23 C22 C24 118.9(9) . . ? C18 C23 C22 120.4(9) . . ? C18 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? O1 C24 O2 128.3(9) . . ? O1 C24 C22 115.9(8) . . ? O2 C24 C22 115.7(9) . . ? O5 C25 O6 122.2(10) . . ? O5 C25 O6' 38.3(11) . . ? O6 C25 O6' 110.2(15) . . ? O5 C25 C26 125.2(9) . . ? O6 C25 C26 112.1(10) . . ? O6' C25 C26 116.3(14) . . ? C27 C26 C25 115.4(9) . . ? C27 C26 H26A 108.4 . . ? C25 C26 H26A 108.4 . . ? C27 C26 H26B 108.4 . . ? C25 C26 H26B 108.4 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 132.2(11) . . ? C26 C27 H27A 104.2 . . ? C28 C27 H27A 104.2 . . ? C26 C27 H27B 104.2 . . ? C28 C27 H27B 104.2 . . ? H27A C27 H27B 105.5 . . ? C27 C28 C29 107.1(9) . . ? C27 C28 H28A 110.3 . . ? C29 C28 H28A 110.3 . . ? C27 C28 H28B 110.3 . . ? C29 C28 H28B 110.3 . . ? H28A C28 H28B 108.6 . . ? C30 C29 C28 100.8(8) . . ? C30 C29 H29A 111.6 . . ? C28 C29 H29A 111.6 . . ? C30 C29 H29B 111.6 . . ? C28 C29 H29B 111.6 . . ? H29A C29 H29B 109.4 . . ? C29 C30 C31 115.6(9) . . ? C29 C30 H30A 108.4 . . ? C31 C30 H30A 108.4 . . ? C29 C30 H30B 108.4 . . ? C31 C30 H30B 108.4 . . ? H30A C30 H30B 107.4 . . ? O8 C31 O7 126.3(10) . . ? O8 C31 O8' 56.8(9) . . ? O7 C31 O8' 88.7(10) . . ? O8 C31 C30 122.2(11) . . ? O7 C31 C30 111.4(9) . . ? O8' C31 C30 134.2(12) . . ? C31 O8' Zn1 96.2(7) . . ? C25 O6' Zn2 91.5(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 N1 C1 46.4(8) . . . . ? O7 Zn1 N1 C1 -94.5(8) . . . . ? O3 Zn1 N1 C1 159.5(7) . . . . ? O8' Zn1 N1 C1 -36.5(9) . . . . ? O1 Zn1 N1 C5 -131.3(8) . . . . ? O7 Zn1 N1 C5 87.8(8) . . . . ? O3 Zn1 N1 C5 -18.2(8) . . . . ? O8' Zn1 N1 C5 145.8(8) . . . . ? O7 Zn1 O1 C24 -57.9(14) . . . . ? O3 Zn1 O1 C24 68.1(14) . . . . ? N1 Zn1 O1 C24 171.9(14) . . . . ? O8' Zn1 O1 C24 -74.7(14) . . . . ? O5 Zn2 O2 C24 100.4(9) . . . . ? O4 Zn2 O2 C24 -38.6(9) . . . . ? N2 Zn2 O2 C24 -139.4(8) 4_565 . . . ? O6' Zn2 O2 C24 121(1) . . . . ? O1 Zn1 O3 C12 -40.8(9) . . . . ? O7 Zn1 O3 C12 101.7(9) . . . . ? N1 Zn1 O3 C12 -139.4(8) . . . . ? O8' Zn1 O3 C12 64.6(10) . . . . ? O5 Zn2 O4 C12 -55.5(18) . . . . ? O2 Zn2 O4 C12 67.7(18) . . . . ? N2 Zn2 O4 C12 172.4(17) 4_565 . . . ? O6' Zn2 O4 C12 -81(2) . . . . ? O2 Zn2 O5 C25 -174.7(9) . . . . ? O4 Zn2 O5 C25 -48.0(11) . . . . ? N2 Zn2 O5 C25 76.4(10) 4_565 . . . ? O6' Zn2 O5 C25 79.6(15) . . . . ? O1 Zn1 O7 C31 -48.7(11) . . . . ? O3 Zn1 O7 C31 -179.2(9) . . . . ? N1 Zn1 O7 C31 73.4(10) . . . . ? O8' Zn1 O7 C31 -27.5(9) . . . . ? C5 N1 C1 C2 -1.0(15) . . . . ? Zn1 N1 C1 C2 -178.9(8) . . . . ? N1 C1 C2 C3 -1.1(16) . . . . ? C1 C2 C3 C4 2.1(15) . . . . ? C1 C2 C3 C6 179.8(9) . . . . ? C6 C3 C4 C5 -178.8(11) . . . . ? C2 C3 C4 C5 -1.2(16) . . . . ? C3 C4 C5 N1 -0.8(18) . . . . ? C1 N1 C5 C4 2.0(16) . . . . ? Zn1 N1 C5 C4 179.7(9) . . . . ? C4 C3 C6 C7 -40.1(14) . . . . ? C2 C3 C6 C7 142.4(10) . . . . ? C4 C3 C6 C11 143.7(11) . . . . ? C2 C3 C6 C11 -33.8(14) . . . . ? C3 C6 C7 C8 -176(1) . . . . ? C11 C6 C7 C8 0.4(15) . . . . ? C6 C7 C8 C9 -0.2(17) . . . . ? C7 C8 C9 C10 -0.4(17) . . . . ? C8 C9 C10 C11 0.7(13) . . . . ? C8 C9 C10 C12 -179.5(9) . . . 4_464 ? C9 C10 C11 C6 -0.5(13) . . . . ? C12 C10 C11 C6 179.7(9) 4_464 . . . ? C3 C6 C11 C10 176.4(8) . . . . ? C7 C6 C11 C10 0.0(14) . . . . ? Zn2 O4 C12 O3 -9(2) . . . . ? Zn2 O4 C12 C10 171.3(12) . . . 4_565 ? Zn1 O3 C12 O4 -9.3(14) . . . . ? Zn1 O3 C12 C10 170.4(6) . . . 4_565 ? C17 N2 C13 C14 0.0(15) . . . . ? Zn2 N2 C13 C14 -179.7(8) 4_464 . . . ? N2 C13 C14 C15 1.3(16) . . . . ? C13 C14 C15 C16 -1.7(16) . . . . ? C13 C14 C15 C18 -178(1) . . . . ? C14 C15 C16 C17 0.8(16) . . . . ? C18 C15 C16 C17 177.1(9) . . . . ? C15 C16 C17 N2 0.6(15) . . . . ? C13 N2 C17 C16 -0.9(14) . . . . ? Zn2 N2 C17 C16 178.7(7) 4_464 . . . ? C16 C15 C18 C23 38.5(14) . . . . ? C14 C15 C18 C23 -145.2(10) . . . . ? C16 C15 C18 C19 -143.2(11) . . . . ? C14 C15 C18 C19 33.1(13) . . . . ? C23 C18 C19 C20 -4.1(16) . . . . ? C15 C18 C19 C20 177.7(10) . . . . ? C18 C19 C20 C21 1.5(16) . . . . ? C19 C20 C21 C22 2.1(17) . . . . ? C20 C21 C22 C23 -3.2(17) . . . . ? C20 C21 C22 C24 178.2(10) . . . . ? C19 C18 C23 C22 3.0(15) . . . . ? C15 C18 C23 C22 -178.7(8) . . . . ? C21 C22 C23 C18 0.6(14) . . . . ? C24 C22 C23 C18 179.2(9) . . . . ? Zn1 O1 C24 O2 -8(2) . . . . ? Zn1 O1 C24 C22 172.2(9) . . . . ? Zn2 O2 C24 O1 -8.9(16) . . . . ? Zn2 O2 C24 C22 171.1(6) . . . . ? C21 C22 C24 O1 -169.9(10) . . . . ? C23 C22 C24 O1 11.5(13) . . . . ? C21 C22 C24 O2 10.1(14) . . . . ? C23 C22 C24 O2 -168.5(8) . . . . ? Zn2 O5 C25 O6 -17.0(16) . . . . ? Zn2 O5 C25 O6' -99.1(19) . . . . ? Zn2 O5 C25 C26 171.9(10) . . . . ? O5 C25 C26 C27 -29.9(19) . . . . ? O6 C25 C26 C27 158.2(12) . . . . ? O6' C25 C26 C27 -74(2) . . . . ? C25 C26 C27 C28 -32(2) . . . . ? C26 C27 C28 C29 -78.7(14) . . . . ? C27 C28 C29 C30 176.1(9) . . . . ? C28 C29 C30 C31 -63.0(12) . . . . ? Zn1 O7 C31 O8 -9.7(17) . . . . ? Zn1 O7 C31 O8' 36.2(10) . . . . ? Zn1 O7 C31 C30 173.9(8) . . . . ? C29 C30 C31 O8 132.0(13) . . . . ? C29 C30 C31 O7 -51.5(16) . . . . ? C29 C30 C31 O8' 58.8(19) . . . . ? O8 C31 O8' Zn1 105.0(9) . . . . ? O7 C31 O8' Zn1 -31.4(8) . . . . ? C30 C31 O8' Zn1 -150.5(12) . . . . ? O1 Zn1 O8' C31 -170.6(9) . . . . ? O7 Zn1 O8' C31 25.2(7) . . . . ? O3 Zn1 O8' C31 74.1(11) . . . . ? N1 Zn1 O8' C31 -80.1(9) . . . . ? O5 C25 O6' Zn2 51.1(12) . . . . ? O6 C25 O6' Zn2 -65.6(13) . . . . ? C26 C25 O6' Zn2 165.3(9) . . . . ? O5 Zn2 O6' C25 -59.5(13) . . . . ? O2 Zn2 O6' C25 -138.5(12) . . . . ? O4 Zn2 O6' C25 11(2) . . . . ? N2 Zn2 O6' C25 117.5(13) 4_565 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.420 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.053 data_5 _database_code_depnum_ccdc_archive 'CCDC 740530' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 N O4 Zn' _chemical_formula_sum 'C16 H10 N O4 Zn' _chemical_formula_weight 345.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.1155(16) _cell_length_b 10.8732(8) _cell_length_c 12.6378(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.168(1) _cell_angle_gamma 90.00 _cell_volume 2889.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4616 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.716 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6639 _exptl_absorpt_correction_T_max 0.8471 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9172 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3319 _reflns_number_gt 2895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+1.8085P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3319 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0670 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.473702(9) 0.293380(15) 1.136025(14) 0.02537(7) Uani 1 1 d . . . N1 N 0.41358(7) 0.30287(12) 1.00151(11) 0.0287(3) Uani 1 1 d . . . O1 O 0.09888(6) 0.19351(12) 0.76072(11) 0.0385(3) Uani 1 1 d . . . O2 O 0.06444(6) 0.23579(13) 0.59351(11) 0.0401(3) Uani 1 1 d . . . O3 O 0.48615(6) 0.47458(10) 1.16211(9) 0.0304(3) Uani 1 1 d . . . O4 O 0.47256(7) 1.11210(12) 1.17044(12) 0.0487(4) Uani 1 1 d . . . C1 C 0.40165(8) 0.40943(16) 0.95184(14) 0.0325(4) Uani 1 1 d . . . H1 H 0.4233 0.4809 0.9789 0.039 Uiso 1 1 calc R . . C2 C 0.35920(8) 0.42074(16) 0.86276(14) 0.0350(4) Uani 1 1 d . . . H2 H 0.3525 0.4985 0.8293 0.042 Uiso 1 1 calc R . . C3 C 0.32656(8) 0.31850(17) 0.82244(14) 0.0336(4) Uani 1 1 d . . . C4 C 0.33966(11) 0.20744(17) 0.87338(18) 0.0487(6) Uani 1 1 d . . . H4 H 0.3188 0.1345 0.8477 0.058 Uiso 1 1 calc R . . C5 C 0.38307(11) 0.20324(17) 0.96136(17) 0.0459(5) Uani 1 1 d . . . H5 H 0.3917 0.1262 0.9950 0.055 Uiso 1 1 calc R . . C6 C 0.27783(8) 0.32858(18) 0.73021(14) 0.0346(4) Uani 1 1 d . . . C7 C 0.21909(9) 0.27370(17) 0.73636(14) 0.0344(4) Uani 1 1 d . . . H7 H 0.2115 0.2274 0.7977 0.041 Uiso 1 1 calc R . . C8 C 0.17108(8) 0.28529(15) 0.65414(14) 0.0304(4) Uani 1 1 d . . . C9 C 0.18300(9) 0.34969(19) 0.56359(15) 0.0395(4) Uani 1 1 d . . . H9 H 0.1509 0.3563 0.5061 0.047 Uiso 1 1 calc R . . C10 C 0.24160(9) 0.4045(2) 0.55685(16) 0.0475(5) Uani 1 1 d . . . H10 H 0.2495 0.4488 0.4946 0.057 Uiso 1 1 calc R . . C11 C 0.28874(9) 0.3954(2) 0.63982(16) 0.0435(5) Uani 1 1 d . . . H11 H 0.3285 0.4348 0.6351 0.052 Uiso 1 1 calc R . . C12 C 0.10650(8) 0.23402(15) 0.67035(14) 0.0294(3) Uani 1 1 d . . . C13 C 0.5000 0.52754(19) 1.2500 0.0255(4) Uani 1 2 d S . . C14 C 0.5000 0.6653(2) 1.2500 0.0257(4) Uani 1 2 d S . . C15 C 0.47312(9) 0.72980(15) 1.16214(14) 0.0312(4) Uani 1 1 d . . . H15 H 0.4546 0.6864 1.1018 0.037 Uiso 1 1 calc R . . C16 C 0.47320(8) 0.85689(15) 1.16224(14) 0.0338(4) Uani 1 1 d . . . H16 H 0.4548 0.9004 1.1019 0.041 Uiso 1 1 calc R . . C17 C 0.5000 0.9213(2) 1.2500 0.0286(5) Uani 1 2 d S . . C18 C 0.5000 1.0593(2) 1.2500 0.0334(5) 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 Zn1 0.02902(12) 0.01759(10) 0.02763(12) 0.00026(7) -0.00777(7) 0.00027(7) N1 0.0272(7) 0.0276(7) 0.0299(7) 0.0006(5) -0.0050(6) -0.0019(5) O1 0.0330(7) 0.0448(8) 0.0372(7) 0.0046(5) 0.0009(5) -0.0059(5) O2 0.0291(6) 0.0495(8) 0.0395(7) 0.0044(6) -0.0097(5) -0.0082(6) O3 0.0422(7) 0.0173(5) 0.0306(6) -0.0017(4) -0.0037(5) -0.0032(5) O4 0.0647(10) 0.0190(6) 0.0592(9) 0.0067(6) -0.0121(7) 0.0016(6) C1 0.0317(9) 0.0284(8) 0.0359(9) 0.0021(7) -0.0060(7) -0.0061(7) C2 0.0342(9) 0.0303(9) 0.0386(9) 0.0085(7) -0.0074(7) -0.0042(7) C3 0.0266(8) 0.0395(10) 0.0334(9) 0.0053(7) -0.0056(7) -0.0049(7) C4 0.0544(13) 0.0326(10) 0.0534(12) 0.0041(8) -0.0257(10) -0.0135(9) C5 0.0547(12) 0.0285(9) 0.0494(12) 0.0071(8) -0.0232(10) -0.0068(8) C6 0.0296(9) 0.0403(9) 0.0320(9) 0.0046(7) -0.0078(7) -0.0045(7) C7 0.0324(9) 0.0386(10) 0.0307(9) 0.0059(7) -0.0057(7) -0.0061(7) C8 0.0277(8) 0.0326(9) 0.0297(8) -0.0015(6) -0.0044(7) -0.0017(7) C9 0.0342(9) 0.0510(11) 0.0314(9) 0.0066(8) -0.0080(7) -0.0036(8) C10 0.0413(11) 0.0645(14) 0.0354(10) 0.0185(9) -0.0031(8) -0.0092(10) C11 0.0329(10) 0.0545(12) 0.0421(10) 0.0118(9) -0.0032(8) -0.0111(9) C12 0.0281(8) 0.0250(8) 0.0342(9) -0.0026(6) -0.0022(7) -0.0006(6) C13 0.0277(11) 0.018(1) 0.0301(11) 0.000 -0.0012(9) 0.000 C14 0.0316(12) 0.0169(10) 0.0281(11) 0.000 -0.0009(9) 0.000 C15 0.0416(10) 0.0207(8) 0.0295(8) -0.0012(6) -0.0065(7) -0.0010(6) C16 0.0442(10) 0.0209(8) 0.0343(9) 0.0041(6) -0.0080(7) 0.0009(7) C17 0.0320(12) 0.0162(10) 0.0368(12) 0.000 -0.0007(10) 0.000 C18 0.0358(13) 0.0188(11) 0.0455(14) 0.000 0.0026(11) 0.000 _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 O3 2.0110(11) . ? Zn1 O4 2.0191(13) 1_545 ? Zn1 N1 2.0306(14) . ? Zn1 O2 2.0605(13) 8_556 ? Zn1 O1 2.1053(14) 7_557 ? Zn1 Zn1 2.9926(4) 2_657 ? N1 C1 1.331(2) . ? N1 C5 1.337(2) . ? O1 C12 1.248(2) . ? O1 Zn1 2.1053(14) 7_557 ? O2 C12 1.256(2) . ? O2 Zn1 2.0605(13) 8_455 ? O3 C13 1.2618(15) . ? O4 C18 1.2535(17) . ? O4 Zn1 2.0191(13) 1_565 ? C1 C2 1.380(2) . ? C1 H1 0.9500 . ? C2 C3 1.381(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 C6 1.488(2) . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.385(2) . ? C6 C11 1.391(3) . ? C7 C8 1.391(2) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 C12 1.504(2) . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C13 O3 1.2618(15) 2_657 ? C13 C14 1.498(3) . ? C14 C15 1.391(2) 2_657 ? C14 C15 1.391(2) . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C16 1.388(2) 2_657 ? C17 C18 1.501(3) . ? C18 O4 1.2535(17) 2_657 ? 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 O3 Zn1 O4 157.67(6) . 1_545 ? O3 Zn1 N1 98.63(5) . . ? O4 Zn1 N1 102.19(6) 1_545 . ? O3 Zn1 O2 94.74(5) . 8_556 ? O4 Zn1 O2 86.29(6) 1_545 8_556 ? N1 Zn1 O2 108.39(6) . 8_556 ? O3 Zn1 O1 85.63(5) . 7_557 ? O4 Zn1 O1 84.78(6) 1_545 7_557 ? N1 Zn1 O1 94.61(6) . 7_557 ? O2 Zn1 O1 156.63(5) 8_556 7_557 ? O3 Zn1 Zn1 79.08(3) . 2_657 ? O4 Zn1 Zn1 78.65(4) 1_545 2_657 ? N1 Zn1 Zn1 162.88(4) . 2_657 ? O2 Zn1 Zn1 88.73(4) 8_556 2_657 ? O1 Zn1 Zn1 68.35(4) 7_557 2_657 ? C1 N1 C5 117.52(15) . . ? C1 N1 Zn1 121.10(11) . . ? C5 N1 Zn1 121.35(12) . . ? C12 O1 Zn1 134.78(12) . 7_557 ? C12 O2 Zn1 113.92(12) . 8_455 ? C13 O3 Zn1 127.44(11) . . ? C18 O4 Zn1 127.32(13) . 1_565 ? N1 C1 C2 122.94(16) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.69(16) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 117.28(16) . . ? C2 C3 C6 121.12(16) . . ? C4 C3 C6 121.58(16) . . ? C5 C4 C3 119.67(16) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 122.88(16) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C7 C6 C11 119.13(16) . . ? C7 C6 C3 118.95(16) . . ? C11 C6 C3 121.87(16) . . ? C6 C7 C8 121.02(16) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 119.28(16) . . ? C9 C8 C12 122.33(15) . . ? C7 C8 C12 118.26(16) . . ? C10 C9 C8 119.96(16) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 120.63(17) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 119.94(17) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? O1 C12 O2 124.94(16) . . ? O1 C12 C8 116.66(15) . . ? O2 C12 C8 118.40(15) . . ? O3 C13 O3 125.7(2) . 2_657 ? O3 C13 C14 117.15(10) . . ? O3 C13 C14 117.15(10) 2_657 . ? C15 C14 C15 119.4(2) 2_657 . ? C15 C14 C13 120.3(1) 2_657 . ? C15 C14 C13 120.3(1) . . ? C16 C15 C14 120.23(16) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.35(16) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C16 119.4(2) . 2_657 ? C16 C17 C18 120.28(10) . . ? C16 C17 C18 120.28(10) 2_657 . ? O4 C18 O4 125.5(2) 2_657 . ? O4 C18 C17 117.26(11) 2_657 . ? O4 C18 C17 117.26(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 O3 Zn1 N1 C1 8.74(15) . . . . ? O4 Zn1 N1 C1 -179.35(14) 1_545 . . . ? O2 Zn1 N1 C1 -89.22(14) 8_556 . . . ? O1 Zn1 N1 C1 95.01(14) 7_557 . . . ? Zn1 Zn1 N1 C1 89.64(19) 2_657 . . . ? O3 Zn1 N1 C5 -169.22(17) . . . . ? O4 Zn1 N1 C5 2.69(18) 1_545 . . . ? O2 Zn1 N1 C5 92.82(17) 8_556 . . . ? O1 Zn1 N1 C5 -82.95(17) 7_557 . . . ? Zn1 Zn1 N1 C5 -88.3(2) 2_657 . . . ? O4 Zn1 O3 C13 -5.6(2) 1_545 . . . ? N1 Zn1 O3 C13 153.14(10) . . . . ? O2 Zn1 O3 C13 -97.43(11) 8_556 . . . ? O1 Zn1 O3 C13 59.13(10) 7_557 . . . ? Zn1 Zn1 O3 C13 -9.64(9) 2_657 . . . ? C5 N1 C1 C2 0.7(3) . . . . ? Zn1 N1 C1 C2 -177.31(14) . . . . ? N1 C1 C2 C3 0.7(3) . . . . ? C1 C2 C3 C4 -1.5(3) . . . . ? C1 C2 C3 C6 176.56(17) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C6 C3 C4 C5 -177.1(2) . . . . ? C1 N1 C5 C4 -1.3(3) . . . . ? Zn1 N1 C5 C4 176.73(19) . . . . ? C3 C4 C5 N1 0.5(4) . . . . ? C2 C3 C6 C7 -131.4(2) . . . . ? C4 C3 C6 C7 46.5(3) . . . . ? C2 C3 C6 C11 46.1(3) . . . . ? C4 C3 C6 C11 -136.0(2) . . . . ? C11 C6 C7 C8 -0.5(3) . . . . ? C3 C6 C7 C8 177.09(17) . . . . ? C6 C7 C8 C9 1.9(3) . . . . ? C6 C7 C8 C12 -174.10(17) . . . . ? C7 C8 C9 C10 -1.8(3) . . . . ? C12 C8 C9 C10 174.09(19) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C6 1.3(3) . . . . ? C7 C6 C11 C10 -1.1(3) . . . . ? C3 C6 C11 C10 -178.6(2) . . . . ? Zn1 O1 C12 O2 -42.5(3) 7_557 . . . ? Zn1 O1 C12 C8 136.85(13) 7_557 . . . ? Zn1 O2 C12 O1 14.7(2) 8_455 . . . ? Zn1 O2 C12 C8 -164.64(12) 8_455 . . . ? C9 C8 C12 O1 -169.91(17) . . . . ? C7 C8 C12 O1 6.0(2) . . . . ? C9 C8 C12 O2 9.5(3) . . . . ? C7 C8 C12 O2 -174.58(16) . . . . ? Zn1 O3 C13 O3 6.24(6) . . . 2_657 ? Zn1 O3 C13 C14 -173.76(6) . . . . ? O3 C13 C14 C15 -166.94(11) . . . 2_657 ? O3 C13 C14 C15 13.06(11) 2_657 . . 2_657 ? O3 C13 C14 C15 13.06(11) . . . . ? O3 C13 C14 C15 -166.94(11) 2_657 . . . ? C15 C14 C15 C16 0.05(12) 2_657 . . . ? C13 C14 C15 C16 -179.95(12) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C15 C16 C17 C16 0.05(12) . . . 2_657 ? C15 C16 C17 C18 -179.95(12) . . . . ? Zn1 O4 C18 O4 8.85(8) 1_565 . . 2_657 ? Zn1 O4 C18 C17 -171.15(8) 1_565 . . . ? C16 C17 C18 O4 -176.85(13) . . . 2_657 ? C16 C17 C18 O4 3.15(13) 2_657 . . 2_657 ? C16 C17 C18 O4 3.15(13) . . . . ? C16 C17 C18 O4 -176.85(13) 2_657 . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.323 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.051