# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 Co N4 O6 S2' _chemical_formula_sum 'C23 H14 Co N4 O6 S2' _chemical_formula_weight 565.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3925(12) _cell_length_b 10.0156(16) _cell_length_c 12.6690(16) _cell_angle_alpha 84.282(2) _cell_angle_beta 80.105(2) _cell_angle_gamma 71.028(2) _cell_volume 1109.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5268 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 574 _exptl_absorpt_coefficient_mu 1.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7857 _exptl_absorpt_correction_T_max 0.8628 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7239 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4837 _reflns_number_gt 4344 _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^)+(0.0700P)^2^+0.0100P] 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 4837 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C1 C 1.01976(19) 0.56781(18) 0.18665(13) 0.0117(3) Uani 1 1 d . . 1 C2 C 1.03988(19) 0.41973(18) 0.23180(13) 0.0118(3) Uani 1 1 d . . 1 C3 C 1.02262(19) 0.39183(18) 0.34212(13) 0.0123(3) Uani 1 1 d . . 1 H3 H 1.0050 0.4640 0.3882 0.015 Uiso 1 1 calc R . 1 C4 C 1.03178(19) 0.25480(18) 0.38379(13) 0.0121(3) Uani 1 1 d . . 1 C5 C 1.0135(2) 0.22527(19) 0.50306(13) 0.0147(4) Uani 1 1 d . . 1 C6 C 1.05861(19) 0.14582(18) 0.31536(13) 0.0128(3) Uani 1 1 d . . 1 H6 H 1.0658 0.0548 0.3434 0.015 Uiso 1 1 calc R . 1 C7 C 1.07470(19) 0.17389(18) 0.20436(13) 0.0122(3) Uani 1 1 d . . 1 C8 C 1.08649(19) 0.06256(18) 0.12869(13) 0.0127(3) Uani 1 1 d . . 1 C9 C 1.06752(19) 0.31047(18) 0.16285(13) 0.0124(3) Uani 1 1 d . . 1 H9 H 1.0812 0.3286 0.0890 0.015 Uiso 1 1 calc R . 1 C10 C 0.7572(2) 0.98865(19) 0.26849(14) 0.0171(4) Uani 1 1 d . . 1 H10 H 0.8333 1.0123 0.2931 0.021 Uiso 1 1 calc R . 1 C11 C 0.6407(2) 0.8950(2) 0.18038(15) 0.0209(4) Uani 1 1 d . . 1 H11 H 0.6230 0.8406 0.1318 0.025 Uiso 1 1 calc R . 1 C12 C 0.5310(2) 0.9816(2) 0.25042(15) 0.0213(4) Uani 1 1 d . . 1 H12 H 0.4266 0.9972 0.2586 0.026 Uiso 1 1 calc R . 1 C13 C 0.5405(2) 1.1442(2) 0.38443(14) 0.0171(4) Uani 1 1 d . . 1 C14 C 0.4050(2) 1.2491(2) 0.38758(15) 0.0223(4) Uani 1 1 d . . 1 H14 H 0.3395 1.2636 0.3372 0.027 Uiso 1 1 calc R . 1 C15 C 0.3757(2) 1.3336(2) 0.47684(15) 0.0217(4) Uani 1 1 d . . 1 H15 H 0.2876 1.4095 0.4916 0.026 Uiso 1 1 calc R . 1 C16 C 0.4888(2) 1.2934(2) 0.53917(14) 0.0176(4) Uani 1 1 d . . 1 C17 C 0.5019(2) 1.35349(19) 0.63516(14) 0.0161(4) Uani 1 1 d . . 1 C18 C 0.6182(2) 1.3164(2) 0.69474(15) 0.0193(4) Uani 1 1 d . . 1 H18 H 0.7094 1.2451 0.6763 0.023 Uiso 1 1 calc R . 1 C19 C 0.5879(2) 1.3958(2) 0.78680(14) 0.0188(4) Uani 1 1 d . . 1 H19 H 0.6558 1.3833 0.8351 0.023 Uiso 1 1 calc R . 1 C20 C 0.4470(2) 1.4927(2) 0.79574(14) 0.0169(4) Uani 1 1 d . . 1 C21 C 0.4331(2) 1.7027(2) 0.89406(15) 0.0204(4) Uani 1 1 d . . 1 H21 H 0.5236 1.7179 0.8618 0.024 Uiso 1 1 calc R . 1 C22 C 0.2438(2) 1.61270(19) 0.93945(13) 0.0155(4) Uani 1 1 d . . 1 H22 H 0.1840 1.5540 0.9422 0.019 Uiso 1 1 calc R . 1 C23 C 0.3266(2) 1.7815(2) 0.96915(15) 0.0189(4) Uani 1 1 d . . 1 H23 H 0.3321 1.8616 0.9975 0.023 Uiso 1 1 calc R . 1 Co1 Co 0.99717(3) 0.81183(2) 0.099705(16) 0.01111(9) Uani 1 1 d . . 1 N1 N 0.78153(18) 0.90024(16) 0.19240(11) 0.0156(3) Uani 1 1 d . . 1 N2 N 0.60629(18) 1.04100(16) 0.30656(12) 0.0166(3) Uani 1 1 d . . 1 N3 N 0.37993(17) 1.59497(16) 0.87518(12) 0.0162(3) Uani 1 1 d . . 1 N4 N 0.20821(17) 1.72478(16) 0.99733(11) 0.0147(3) Uani 1 1 d . . 1 O1 O 0.96829(14) 0.60443(12) 0.09888(9) 0.0140(3) Uani 1 1 d . . 1 O2 O 1.05598(14) 0.65440(12) 0.23510(9) 0.0140(3) Uani 1 1 d . . 1 O3 O 0.94713(17) 0.34368(14) 0.55588(10) 0.0217(3) Uani 1 1 d . . 1 H3A H 0.9506 0.3260 0.6202 0.033 Uiso 1 1 calc R . 1 O4 O 1.05241(17) 0.10893(14) 0.54509(10) 0.0237(3) Uani 1 1 d . . 1 O5 O 1.07656(15) -0.05426(13) 0.16988(9) 0.0155(3) Uani 1 1 d . . 1 O6 O 1.10431(14) 0.09325(13) 0.02936(9) 0.0156(3) Uani 1 1 d . . 1 S1 S 0.63510(5) 1.14586(5) 0.48978(4) 0.01931(12) Uani 1 1 d . . 1 S2 S 0.35100(5) 1.49147(5) 0.69174(4) 0.01987(13) Uani 1 1 d . . 1 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 C1 0.0128(8) 0.0120(8) 0.0087(7) -0.0029(6) 0.0024(6) -0.0029(6) C2 0.0132(8) 0.0113(8) 0.0104(7) -0.0004(6) -0.0012(6) -0.0033(6) C3 0.0142(8) 0.0115(8) 0.0116(8) -0.0024(6) -0.0016(6) -0.0041(6) C4 0.0137(8) 0.0128(8) 0.0094(7) -0.0006(6) -0.0019(6) -0.0034(6) C5 0.0203(9) 0.0150(9) 0.0114(8) -0.0005(7) -0.0030(7) -0.0089(7) C6 0.0164(8) 0.0108(8) 0.0109(8) 0.0002(6) -0.0021(6) -0.0040(6) C7 0.0139(8) 0.0120(8) 0.0101(7) -0.0029(6) -0.0006(6) -0.0029(6) C8 0.0147(8) 0.0116(8) 0.0110(7) -0.0015(6) -0.0015(6) -0.0031(6) C9 0.0141(8) 0.0137(8) 0.0086(7) -0.0010(6) -0.0006(6) -0.0036(6) C10 0.0179(9) 0.0185(9) 0.0124(8) -0.0027(7) -0.0011(7) -0.0020(7) C11 0.0264(10) 0.0211(10) 0.0168(8) -0.0054(7) 0.0000(7) -0.0100(8) C12 0.0200(10) 0.0254(10) 0.0205(9) -0.0053(8) 0.0017(7) -0.0110(8) C13 0.0166(9) 0.0198(9) 0.0136(8) -0.0043(7) 0.0011(7) -0.0047(7) C14 0.0173(9) 0.0285(11) 0.0185(9) -0.0077(8) -0.0010(7) -0.0027(8) C15 0.0156(9) 0.0246(10) 0.0196(9) -0.0086(8) 0.0012(7) 0.0013(7) C16 0.0154(9) 0.0180(9) 0.0154(8) -0.0055(7) 0.0033(7) -0.0015(7) C17 0.0145(8) 0.0159(9) 0.0137(8) -0.0044(7) 0.0036(6) -0.0008(7) C18 0.0164(9) 0.0183(9) 0.0184(9) -0.0040(7) 0.0005(7) 0.0002(7) C19 0.0161(9) 0.0219(10) 0.0160(8) -0.0028(7) -0.0021(7) -0.0023(7) C20 0.0167(9) 0.0201(9) 0.0124(8) -0.0050(7) 0.0009(7) -0.0042(7) C21 0.0193(9) 0.0237(10) 0.0188(9) -0.0032(8) 0.0022(7) -0.0094(8) C22 0.0164(9) 0.0175(9) 0.0115(8) -0.0023(7) -0.0004(6) -0.0043(7) C23 0.0222(10) 0.0171(9) 0.0178(8) -0.0040(7) 0.0008(7) -0.0076(7) Co1 0.01760(15) 0.00783(14) 0.00688(13) -0.00116(9) -0.00028(9) -0.00316(10) N1 0.0217(8) 0.0132(7) 0.0096(6) -0.0007(6) 0.0010(6) -0.0039(6) N2 0.0179(8) 0.0163(8) 0.0131(7) -0.0048(6) 0.0025(6) -0.0033(6) N3 0.0172(8) 0.0162(8) 0.0134(7) -0.0047(6) 0.0012(6) -0.0033(6) N4 0.0177(8) 0.0134(7) 0.0117(7) -0.0019(6) -0.0005(6) -0.0036(6) O1 0.0213(7) 0.0099(6) 0.0098(5) 0.0005(4) -0.0026(5) -0.0037(5) O2 0.0222(7) 0.0106(6) 0.0110(5) 0.0004(5) -0.0031(5) -0.0074(5) O3 0.0392(8) 0.0164(7) 0.0081(5) -0.0023(5) -0.0006(5) -0.0077(6) O4 0.0408(9) 0.0152(7) 0.0122(6) 0.0014(5) -0.0042(6) -0.0054(6) O5 0.0251(7) 0.0109(6) 0.0112(5) -0.0015(5) -0.0012(5) -0.0071(5) O6 0.0228(7) 0.0138(6) 0.0083(5) -0.0007(5) -0.0021(5) -0.0031(5) S1 0.0192(2) 0.0194(2) 0.0139(2) -0.00632(18) -0.00133(17) 0.00238(18) S2 0.0153(2) 0.0230(3) 0.0164(2) -0.00902(18) -0.00196(17) 0.00283(18) _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 C1 O1 1.262(2) . ? C1 O2 1.271(2) . ? C1 C2 1.499(2) . ? C2 C3 1.390(2) . ? C2 C9 1.399(2) . ? C3 C4 1.401(2) . ? C3 H3 0.9300 . ? C4 C6 1.393(2) . ? C4 C5 1.502(2) . ? C5 O4 1.200(2) . ? C5 O3 1.333(2) . ? C6 C7 1.398(2) . ? C6 H6 0.9300 . ? C7 C9 1.400(2) . ? C7 C8 1.507(2) . ? C8 O5 1.258(2) . ? C8 O6 1.261(2) . ? C9 H9 0.9300 . ? C10 N1 1.315(2) . ? C10 N2 1.360(2) . ? C10 H10 0.9300 . ? C11 C12 1.363(3) . ? C11 N1 1.375(3) . ? C11 H11 0.9300 . ? C12 N2 1.375(2) . ? C12 H12 0.9300 . ? C13 C14 1.358(3) . ? C13 N2 1.415(2) . ? C13 S1 1.7299(19) . ? C14 C15 1.415(3) . ? C14 H14 0.9300 . ? C15 C16 1.364(3) . ? C15 H15 0.9300 . ? C16 C17 1.450(3) . ? C16 S1 1.7411(18) . ? C17 C18 1.365(3) . ? C17 S2 1.7341(17) . ? C18 C19 1.413(2) . ? C18 H18 0.9300 . ? C19 C20 1.357(2) . ? C19 H19 0.9300 . ? C20 N3 1.423(2) . ? C20 S2 1.7230(19) . ? C21 C23 1.356(3) . ? C21 N3 1.383(2) . ? C21 H21 0.9300 . ? C22 N4 1.321(2) . ? C22 N3 1.361(2) . ? C22 H22 0.9300 . ? C23 N4 1.386(2) . ? C23 H23 0.9300 . ? Co1 O6 2.0303(12) 2_765 ? Co1 O5 2.0642(13) 1_565 ? Co1 N1 2.1187(15) . ? Co1 N4 2.1423(15) 1_644 ? Co1 O1 2.1818(13) . ? Co1 O2 2.2257(12) . ? N4 Co1 2.1423(15) 1_466 ? O3 H3A 0.8200 . ? O5 Co1 2.0642(13) 1_545 ? O6 Co1 2.0304(12) 2_765 ? 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 C1 O2 120.51(15) . . ? O1 C1 C2 118.89(15) . . ? O2 C1 C2 120.59(15) . . ? C3 C2 C9 119.75(16) . . ? C3 C2 C1 120.30(15) . . ? C9 C2 C1 119.85(15) . . ? C2 C3 C4 119.94(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C6 C4 C3 120.47(15) . . ? C6 C4 C5 119.86(15) . . ? C3 C4 C5 119.67(15) . . ? O4 C5 O3 124.49(16) . . ? O4 C5 C4 123.86(16) . . ? O3 C5 C4 111.64(15) . . ? C4 C6 C7 119.70(16) . . ? C4 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C9 119.73(15) . . ? C6 C7 C8 120.98(15) . . ? C9 C7 C8 119.09(15) . . ? O5 C8 O6 124.88(16) . . ? O5 C8 C7 117.14(14) . . ? O6 C8 C7 117.98(15) . . ? C2 C9 C7 120.38(15) . . ? C2 C9 H9 119.8 . . ? C7 C9 H9 119.8 . . ? N1 C10 N2 111.14(17) . . ? N1 C10 H10 124.4 . . ? N2 C10 H10 124.4 . . ? C12 C11 N1 109.79(17) . . ? C12 C11 H11 125.1 . . ? N1 C11 H11 125.1 . . ? C11 C12 N2 105.92(17) . . ? C11 C12 H12 127.0 . . ? N2 C12 H12 127.0 . . ? C14 C13 N2 127.13(17) . . ? C14 C13 S1 112.78(14) . . ? N2 C13 S1 120.09(14) . . ? C13 C14 C15 111.74(17) . . ? C13 C14 H14 124.1 . . ? C15 C14 H14 124.1 . . ? C16 C15 C14 113.80(17) . . ? C16 C15 H15 123.1 . . ? C14 C15 H15 123.1 . . ? C15 C16 C17 130.25(17) . . ? C15 C16 S1 111.01(14) . . ? C17 C16 S1 118.74(14) . . ? C18 C17 C16 130.00(17) . . ? C18 C17 S2 110.52(13) . . ? C16 C17 S2 119.46(14) . . ? C17 C18 C19 114.15(16) . . ? C17 C18 H18 122.9 . . ? C19 C18 H18 122.9 . . ? C20 C19 C18 111.41(17) . . ? C20 C19 H19 124.3 . . ? C18 C19 H19 124.3 . . ? C19 C20 N3 127.29(17) . . ? C19 C20 S2 112.83(13) . . ? N3 C20 S2 119.76(13) . . ? C23 C21 N3 106.04(17) . . ? C23 C21 H21 127.0 . . ? N3 C21 H21 127.0 . . ? N4 C22 N3 110.64(16) . . ? N4 C22 H22 124.7 . . ? N3 C22 H22 124.7 . . ? C21 C23 N4 109.72(17) . . ? C21 C23 H23 125.1 . . ? N4 C23 H23 125.1 . . ? O6 Co1 O5 111.91(5) 2_765 1_565 ? O6 Co1 N1 86.06(5) 2_765 . ? O5 Co1 N1 88.31(6) 1_565 . ? O6 Co1 N4 90.53(5) 2_765 1_644 ? O5 Co1 N4 93.96(6) 1_565 1_644 ? N1 Co1 N4 176.43(5) . 1_644 ? O6 Co1 O1 99.40(5) 2_765 . ? O5 Co1 O1 148.68(5) 1_565 . ? N1 Co1 O1 93.82(5) . . ? N4 Co1 O1 85.69(5) 1_644 . ? O6 Co1 O2 157.92(5) 2_765 . ? O5 Co1 O2 89.07(5) 1_565 . ? N1 Co1 O2 87.84(5) . . ? N4 Co1 O2 94.96(5) 1_644 . ? O1 Co1 O2 59.85(4) . . ? C10 N1 C11 106.04(15) . . ? C10 N1 Co1 123.48(13) . . ? C11 N1 Co1 130.03(12) . . ? C10 N2 C12 107.11(15) . . ? C10 N2 C13 125.66(16) . . ? C12 N2 C13 127.11(16) . . ? C22 N3 C21 107.40(15) . . ? C22 N3 C20 125.91(16) . . ? C21 N3 C20 126.42(16) . . ? C22 N4 C23 106.20(15) . . ? C22 N4 Co1 125.87(13) . 1_466 ? C23 N4 Co1 127.58(12) . 1_466 ? C1 O1 Co1 90.89(10) . . ? C1 O2 Co1 88.69(10) . . ? C8 O5 Co1 124.76(11) . 1_545 ? C8 O6 Co1 146.56(12) . 2_765 ? C13 S1 C16 90.67(9) . . ? C20 S2 C17 91.07(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -148.39(16) . . . . ? O2 C1 C2 C3 32.6(2) . . . . ? O1 C1 C2 C9 27.9(2) . . . . ? O2 C1 C2 C9 -151.04(16) . . . . ? C9 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 175.83(16) . . . . ? C2 C3 C4 C6 0.2(3) . . . . ? C2 C3 C4 C5 179.81(16) . . . . ? C6 C4 C5 O4 16.9(3) . . . . ? C3 C4 C5 O4 -162.70(18) . . . . ? C6 C4 C5 O3 -162.22(16) . . . . ? C3 C4 C5 O3 18.2(2) . . . . ? C3 C4 C6 C7 -0.8(3) . . . . ? C5 C4 C6 C7 179.65(15) . . . . ? C4 C6 C7 C9 1.6(3) . . . . ? C4 C6 C7 C8 -173.20(15) . . . . ? C6 C7 C8 O5 2.1(2) . . . . ? C9 C7 C8 O5 -172.72(15) . . . . ? C6 C7 C8 O6 -178.42(16) . . . . ? C9 C7 C8 O6 6.8(2) . . . . ? C3 C2 C9 C7 1.3(3) . . . . ? C1 C2 C9 C7 -175.00(16) . . . . ? C6 C7 C9 C2 -1.9(3) . . . . ? C8 C7 C9 C2 173.00(15) . . . . ? N1 C11 C12 N2 0.0(2) . . . . ? N2 C13 C14 C15 -179.62(18) . . . . ? S1 C13 C14 C15 0.1(2) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C14 C15 C16 C17 179.1(2) . . . . ? C14 C15 C16 S1 -1.1(2) . . . . ? C15 C16 C17 C18 -176.9(2) . . . . ? S1 C16 C17 C18 3.2(3) . . . . ? C15 C16 C17 S2 5.0(3) . . . . ? S1 C16 C17 S2 -174.89(10) . . . . ? C16 C17 C18 C19 -177.4(2) . . . . ? S2 C17 C18 C19 0.9(2) . . . . ? C17 C18 C19 C20 0.2(3) . . . . ? C18 C19 C20 N3 -177.11(18) . . . . ? C18 C19 C20 S2 -1.2(2) . . . . ? N3 C21 C23 N4 0.0(2) . . . . ? N2 C10 N1 C11 0.1(2) . . . . ? N2 C10 N1 Co1 173.11(11) . . . . ? C12 C11 N1 C10 0.0(2) . . . . ? C12 C11 N1 Co1 -172.44(13) . . . . ? O6 Co1 N1 C10 -119.97(14) 2_765 . . . ? O5 Co1 N1 C10 -7.87(14) 1_565 . . . ? O1 Co1 N1 C10 140.85(14) . . . . ? O2 Co1 N1 C10 81.26(14) . . . . ? O6 Co1 N1 C11 51.26(16) 2_765 . . . ? O5 Co1 N1 C11 163.36(16) 1_565 . . . ? O1 Co1 N1 C11 -47.92(16) . . . . ? O2 Co1 N1 C11 -107.50(16) . . . . ? N1 C10 N2 C12 -0.1(2) . . . . ? N1 C10 N2 C13 -176.37(16) . . . . ? C11 C12 N2 C10 0.1(2) . . . . ? C11 C12 N2 C13 176.27(18) . . . . ? C14 C13 N2 C10 143.3(2) . . . . ? S1 C13 N2 C10 -36.3(2) . . . . ? C14 C13 N2 C12 -32.2(3) . . . . ? S1 C13 N2 C12 148.15(16) . . . . ? N4 C22 N3 C21 0.1(2) . . . . ? N4 C22 N3 C20 -174.23(16) . . . . ? C23 C21 N3 C22 -0.1(2) . . . . ? C23 C21 N3 C20 174.20(17) . . . . ? C19 C20 N3 C22 -125.5(2) . . . . ? S2 C20 N3 C22 58.8(2) . . . . ? C19 C20 N3 C21 61.3(3) . . . . ? S2 C20 N3 C21 -114.39(19) . . . . ? N3 C22 N4 C23 0.0(2) . . . . ? N3 C22 N4 Co1 173.62(11) . . . 1_466 ? C21 C23 N4 C22 0.0(2) . . . . ? C21 C23 N4 Co1 -173.51(13) . . . 1_466 ? O2 C1 O1 Co1 2.61(16) . . . . ? C2 C1 O1 Co1 -176.37(13) . . . . ? O6 Co1 O1 C1 -173.39(10) 2_765 . . . ? O5 Co1 O1 C1 6.26(15) 1_565 . . . ? N1 Co1 O1 C1 -86.75(10) . . . . ? N4 Co1 O1 C1 96.79(10) 1_644 . . . ? O2 Co1 O1 C1 -1.48(9) . . . . ? O1 C1 O2 Co1 -2.56(15) . . . . ? C2 C1 O2 Co1 176.41(14) . . . . ? O6 Co1 O2 C1 23.17(17) 2_765 . . . ? O5 Co1 O2 C1 -174.51(10) 1_565 . . . ? N1 Co1 O2 C1 97.15(10) . . . . ? N4 Co1 O2 C1 -80.61(10) 1_644 . . . ? O1 Co1 O2 C1 1.48(9) . . . . ? O6 C8 O5 Co1 -27.3(2) . . . 1_545 ? C7 C8 O5 Co1 152.17(11) . . . 1_545 ? O5 C8 O6 Co1 97.1(2) . . . 2_765 ? C7 C8 O6 Co1 -82.3(3) . . . 2_765 ? C14 C13 S1 C16 -0.56(17) . . . . ? N2 C13 S1 C16 179.16(16) . . . . ? C15 C16 S1 C13 0.92(16) . . . . ? C17 C16 S1 C13 -179.20(17) . . . . ? C19 C20 S2 C17 1.43(16) . . . . ? N3 C20 S2 C17 177.69(16) . . . . ? C18 C17 S2 C20 -1.27(16) . . . . ? C16 C17 S2 C20 177.18(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.82 1.85 2.6451(17) 162.4 2_766 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.443 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 963191' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H18 Co F6 N4 O4 S2' _chemical_formula_sum 'C31 H18 Co F6 N4 O4 S2' _chemical_formula_weight 747.54 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2077(6) _cell_length_b 10.5027(6) _cell_length_c 14.5086(9) _cell_angle_alpha 94.4540(10) _cell_angle_beta 98.6490(10) _cell_angle_gamma 91.2890(10) _cell_volume 1532.19(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3424 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.11 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 754 _exptl_absorpt_coefficient_mu 0.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8002 _exptl_absorpt_correction_T_max 0.8922 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10228 _diffrn_reflns_av_R_equivalents 0.0940 _diffrn_reflns_av_sigmaI/netI 0.0850 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.10 _reflns_number_total 6723 _reflns_number_gt 4735 _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^)+(0.0688P)^2^+0.0369P] 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 6723 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1569 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.027 _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 Co1 Co 0.92179(4) 0.60125(4) 0.18701(3) 0.04227(15) Uani 1 1 d . . 1 F1 F 0.4659(2) 0.52748(19) 0.61572(17) 0.0638(6) Uani 1 1 d . A 1 F2 F 0.37086(19) 0.6608(2) 0.52495(15) 0.0650(6) Uani 1 1 d . A 1 F3 F 0.3227(2) 0.6563(2) 0.66260(18) 0.0720(7) Uani 1 1 d . A 1 F4 F 0.39088(19) 0.9044(2) 0.58773(15) 0.0607(6) Uani 1 1 d . A 1 F5 F 0.4207(2) 0.8922(2) 0.73591(16) 0.0678(6) Uani 1 1 d . A 1 F6 F 0.5747(2) 0.96910(19) 0.66975(17) 0.0650(6) Uani 1 1 d . A 1 N1 N 1.1169(2) 0.6626(3) 0.21018(19) 0.0443(6) Uani 1 1 d . . 1 N2 N 1.3044(2) 0.7469(3) 0.1818(2) 0.0451(6) Uani 1 1 d . . 1 N3 N 0.9028(3) 0.4083(3) 0.1900(2) 0.0489(7) Uani 1 1 d . . 1 N4 N 0.9123(3) 0.2198(3) 0.2448(2) 0.0494(7) Uani 1 1 d . . 1 O1 O 0.9571(2) 0.5935(2) 0.36222(17) 0.0529(6) Uani 1 1 d . B 1 O2 O 0.8059(2) 0.6892(2) 0.26870(17) 0.0533(6) Uani 1 1 d . . 1 O3 O 0.8409(8) 0.6107(8) 1.0604(5) 0.0600(17) Uani 0.50 1 d PDU . 1 O4 O 0.9177(5) 0.8114(6) 1.0529(3) 0.0693(16) Uani 0.50 1 d PDU . 1 O3' O 0.8874(8) 0.6631(10) 1.0532(6) 0.076(3) Uani 0.50 1 d PD . 2 O4' O 0.7120(7) 0.5538(7) 1.0675(4) 0.087(2) Uani 0.50 1 d PD . 2 S1 S 1.33586(7) 0.92827(9) 0.06396(6) 0.0479(2) Uani 1 1 d . . . S2 S 0.93569(9) 0.16341(9) 0.42394(7) 0.0511(2) Uani 1 1 d . . . C1 C 0.8531(3) 0.6550(3) 0.3490(2) 0.0438(7) Uani 1 1 d . . . C2 C 0.7794(3) 0.6860(3) 0.4285(2) 0.0360(6) Uani 1 1 d . B . C3 C 0.6888(3) 0.7826(3) 0.4252(2) 0.0451(8) Uani 1 1 d . . . H3 H 0.6769 0.8314 0.3740 0.054 Uiso 1 1 calc R B . C4 C 0.6166(3) 0.8069(3) 0.4967(2) 0.0439(7) Uani 1 1 d . B . H4 H 0.5576 0.8732 0.4936 0.053 Uiso 1 1 calc R . . C5 C 0.6297(3) 0.7347(3) 0.5734(2) 0.0323(6) Uani 1 1 d . . . C6 C 0.7227(3) 0.6386(3) 0.5771(2) 0.0364(6) Uani 1 1 d . B . H6 H 0.7346 0.5897 0.6284 0.044 Uiso 1 1 calc R . . C7 C 0.7968(3) 0.6151(3) 0.5061(2) 0.0376(7) Uani 1 1 d . . . H7 H 0.8588 0.5514 0.5101 0.045 Uiso 1 1 calc R B . C8 C 0.5384(3) 0.7434(3) 0.6483(2) 0.0355(6) Uani 1 1 d U . . C9 C 0.6260(16) 0.724(2) 0.7422(16) 0.042(3) Uani 0.50 1 d PU . 1 C10 C 0.5878(8) 0.6477(12) 0.8089(9) 0.053(2) Uani 0.50 1 d PU . 1 H10 H 0.5085 0.6000 0.7946 0.064 Uiso 0.50 1 calc PR . 1 C11 C 0.6664(9) 0.6408(9) 0.8983(6) 0.0486(18) Uani 0.50 1 d PU . 1 H11 H 0.6414 0.5851 0.9399 0.058 Uiso 0.50 1 calc PR . 1 C12 C 0.7780(8) 0.7162(9) 0.9221(6) 0.0434(15) Uani 0.50 1 d PDU . 1 C13 C 0.8167(7) 0.7959(8) 0.8585(5) 0.0416(14) Uani 0.50 1 d PU . 1 H13 H 0.8933 0.8471 0.8753 0.050 Uiso 0.50 1 calc PR . 1 C14 C 0.7427(11) 0.8009(9) 0.7692(7) 0.0419(18) Uani 0.50 1 d PU . 1 H14 H 0.7705 0.8552 0.7278 0.050 Uiso 0.50 1 calc PR . 1 C15 C 0.8515(8) 0.7172(9) 1.0179(5) 0.0553(19) Uani 0.50 1 d PDU . 1 C16 C 0.4238(3) 0.6471(3) 0.6130(3) 0.0484(8) Uani 1 1 d . . . C17 C 0.4811(3) 0.8783(3) 0.6602(2) 0.0445(7) Uani 1 1 d . . . C18 C 1.2108(3) 0.6585(3) 0.2875(2) 0.0475(8) Uani 1 1 d . . . H18 H 1.1969 0.6254 0.3430 0.057 Uiso 1 1 calc R . 1 C19 C 1.3273(3) 0.7098(3) 0.2714(3) 0.0525(9) Uani 1 1 d . . . H19 H 1.4067 0.7182 0.3126 0.063 Uiso 1 1 calc R C 1 C20 C 1.1761(3) 0.7160(4) 0.1484(2) 0.0503(8) Uani 1 1 d . . . H20 H 1.1349 0.7308 0.0887 0.060 Uiso 1 1 calc R . 1 C21 C 1.3946(3) 0.8108(3) 0.1341(2) 0.0440(7) Uani 1 1 d . . . C22 C 1.5245(3) 0.7968(4) 0.1381(3) 0.0557(9) Uani 1 1 d . . . H22 H 1.5730 0.7399 0.1746 0.067 Uiso 1 1 calc R . . C23 C 1.5801(3) 0.8788(4) 0.0801(3) 0.0566(9) Uani 1 1 d . . . H23 H 1.6696 0.8807 0.0744 0.068 Uiso 1 1 calc R . . C24 C 1.4911(3) 0.9541(3) 0.0336(2) 0.0431(7) Uani 1 1 d . . . C25 C 0.9490(3) 0.3434(3) 0.2600(3) 0.0471(8) Uani 1 1 d . . . H25 H 1.0015 0.3791 0.3143 0.057 Uiso 1 1 calc R . 1 C26 C 0.8361(4) 0.2039(4) 0.1576(3) 0.0687(11) Uani 1 1 d . . . H26 H 0.7957 0.1284 0.1278 0.082 Uiso 1 1 calc R . 1 C27 C 0.8322(4) 0.3194(4) 0.1248(3) 0.0637(10) Uani 1 1 d . . . H27 H 0.7884 0.3374 0.0665 0.076 Uiso 1 1 calc R D 1 C28 C 0.9443(3) 0.1254(3) 0.3083(3) 0.0498(8) Uani 1 1 d . . . C29 C 0.9838(4) 0.0062(4) 0.2903(3) 0.0684(11) Uani 1 1 d . . . H29 H 0.9923 -0.0300 0.2310 0.082 Uiso 1 1 calc R . . C30 C 1.0107(5) -0.0570(4) 0.3731(3) 0.0679(11) Uani 1 1 d . . . H30 H 1.0396 -0.1403 0.3740 0.081 Uiso 1 1 calc R . . C31 C 0.9907(3) 0.0145(3) 0.4513(3) 0.0492(8) Uani 1 1 d . . . C9' C 0.5995(13) 0.7108(19) 0.7481(14) 0.035(2) Uani 0.50 1 d PU . 2 C10' C 0.5362(8) 0.6325(11) 0.8015(8) 0.0477(18) Uani 0.50 1 d PU . 2 H10' H 0.4519 0.5979 0.7785 0.057 Uiso 0.50 1 calc PR . 2 C11' C 0.5982(9) 0.6056(9) 0.8890(5) 0.0570(17) Uani 0.50 1 d PU . 2 H11' H 0.5555 0.5542 0.9255 0.068 Uiso 0.50 1 calc PR . 2 C12' C 0.7264(11) 0.6570(12) 0.9221(6) 0.055(2) Uani 0.50 1 d PU . 2 C13' C 0.7863(8) 0.7296(10) 0.8709(7) 0.0533(17) Uani 0.50 1 d PU . 2 H13' H 0.8708 0.7636 0.8940 0.064 Uiso 0.50 1 calc PR . 2 C14' C 0.7255(11) 0.7571(10) 0.7818(7) 0.046(2) Uani 0.50 1 d PU . 2 H14' H 0.7706 0.8068 0.7456 0.056 Uiso 0.50 1 calc PR . 2 C15' C 0.7786(8) 0.6196(9) 1.0218(6) 0.0589(18) Uani 0.50 1 d PDU . 2 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 Co1 0.0409(3) 0.0548(3) 0.0337(2) 0.0125(2) 0.00868(18) 0.00726(19) F1 0.0697(13) 0.0408(11) 0.0825(16) 0.0007(10) 0.0204(11) -0.0086(10) F2 0.0537(12) 0.0820(16) 0.0527(13) -0.0017(11) -0.0077(10) -0.0113(10) F3 0.0530(12) 0.0828(17) 0.0856(17) 0.0026(13) 0.0321(12) -0.0091(11) F4 0.0602(12) 0.0622(13) 0.0625(14) 0.0179(11) 0.0081(10) 0.0267(10) F5 0.0861(15) 0.0652(14) 0.0608(14) 0.0042(11) 0.0362(12) 0.0274(12) F6 0.0748(14) 0.0407(11) 0.0796(16) -0.0079(10) 0.0191(12) -0.0014(10) N1 0.0422(14) 0.0506(16) 0.0414(15) 0.0081(12) 0.0082(12) 0.0029(12) N2 0.0414(14) 0.0521(17) 0.0426(15) 0.0070(13) 0.0071(12) 0.0015(12) N3 0.0462(15) 0.0548(18) 0.0449(16) 0.0103(14) 0.0017(13) 0.0010(13) N4 0.0548(16) 0.0494(17) 0.0421(16) 0.0023(13) 0.0030(13) -0.0072(13) O1 0.0474(13) 0.0650(16) 0.0500(14) 0.0047(12) 0.0180(11) 0.0114(11) O2 0.0572(14) 0.0677(16) 0.0387(13) 0.0109(11) 0.0143(11) 0.0117(11) O3 0.050(4) 0.106(5) 0.024(3) 0.019(3) -0.002(3) 0.023(3) O4 0.055(3) 0.111(5) 0.034(3) -0.011(3) -0.016(2) 0.029(3) O3' 0.059(5) 0.119(8) 0.049(4) -0.004(5) 0.008(4) -0.006(4) O4' 0.112(5) 0.098(5) 0.053(4) 0.021(3) 0.005(3) 0.023(4) S1 0.0368(4) 0.0608(5) 0.0480(5) 0.0115(4) 0.0085(3) 0.0029(4) S2 0.0559(5) 0.0462(5) 0.0497(5) 0.0027(4) 0.0037(4) 0.0043(4) C1 0.0453(17) 0.0474(19) 0.0396(18) 0.0020(14) 0.0112(14) -0.0057(14) C2 0.0377(15) 0.0356(16) 0.0335(16) -0.0013(12) 0.0049(12) -0.0061(12) C3 0.0558(19) 0.0469(19) 0.0355(17) 0.0137(14) 0.0104(14) 0.0092(15) C4 0.0506(18) 0.0432(18) 0.0418(18) 0.0136(14) 0.0125(14) 0.0158(14) C5 0.0361(14) 0.0315(15) 0.0294(14) 0.0029(11) 0.0050(11) 0.0017(11) C6 0.0410(15) 0.0378(16) 0.0297(15) 0.0048(12) 0.0024(12) 0.0042(12) C7 0.0367(15) 0.0370(16) 0.0376(16) 0.0013(13) 0.0016(12) 0.0050(12) C8 0.0403(15) 0.0345(15) 0.0312(15) 0.0025(12) 0.0038(12) 0.0027(12) C9 0.044(5) 0.054(4) 0.033(4) 0.010(3) 0.016(4) 0.008(4) C10 0.042(4) 0.072(4) 0.044(4) 0.009(3) 0.004(4) -0.006(4) C11 0.036(4) 0.069(4) 0.043(4) 0.018(3) 0.009(3) -0.012(4) C12 0.038(3) 0.060(4) 0.033(3) 0.011(3) 0.008(3) 0.003(3) C13 0.039(3) 0.057(4) 0.030(3) 0.012(3) 0.006(2) 0.004(3) C14 0.042(4) 0.058(4) 0.027(3) 0.008(3) 0.005(3) 0.000(3) C15 0.047(4) 0.089(5) 0.031(3) 0.011(3) 0.003(3) 0.033(4) C16 0.0435(17) 0.052(2) 0.051(2) 0.0059(16) 0.0104(15) -0.0019(15) C17 0.0482(18) 0.0423(18) 0.0445(19) 0.0014(14) 0.0124(15) 0.0100(14) C18 0.0518(18) 0.048(2) 0.0437(19) 0.0155(15) 0.0046(15) 0.0031(15) C19 0.0473(18) 0.061(2) 0.048(2) 0.0142(17) -0.0025(15) 0.0011(16) C20 0.0423(17) 0.071(2) 0.0382(18) 0.0089(17) 0.0051(14) -0.0018(16) C21 0.0411(16) 0.0491(19) 0.0419(18) 0.0015(15) 0.0075(14) 0.0005(14) C22 0.0471(18) 0.058(2) 0.066(2) 0.0137(19) 0.0134(17) 0.0099(16) C23 0.0406(17) 0.062(2) 0.071(3) 0.0098(19) 0.0180(17) 0.0046(16) C24 0.0387(16) 0.0473(19) 0.0443(18) -0.0027(14) 0.0128(14) -0.0002(14) C25 0.0420(17) 0.0466(19) 0.050(2) 0.0041(15) -0.0024(15) -0.0030(14) C26 0.086(3) 0.064(3) 0.049(2) -0.0058(19) -0.006(2) -0.015(2) C27 0.077(3) 0.070(3) 0.038(2) -0.0006(18) -0.0049(18) -0.002(2) C28 0.0537(19) 0.045(2) 0.049(2) 0.0022(16) 0.0067(16) -0.0101(15) C29 0.110(3) 0.041(2) 0.057(2) -0.0027(17) 0.024(2) -0.002(2) C30 0.105(3) 0.036(2) 0.064(3) 0.0035(18) 0.020(2) 0.001(2) C31 0.0489(18) 0.0369(18) 0.062(2) 0.0053(15) 0.0093(16) -0.0101(14) C9' 0.030(4) 0.054(5) 0.024(4) 0.007(3) 0.011(4) 0.014(4) C10' 0.046(4) 0.066(4) 0.033(3) 0.019(3) 0.003(4) 0.006(4) C11' 0.062(4) 0.077(4) 0.034(3) 0.016(3) 0.005(3) 0.011(3) C12' 0.042(4) 0.082(4) 0.040(4) 0.001(4) 0.000(3) 0.020(4) C13' 0.041(3) 0.083(4) 0.037(3) 0.007(4) 0.004(3) 0.012(3) C14' 0.041(4) 0.070(5) 0.031(4) 0.005(4) 0.010(3) 0.004(4) C15' 0.054(4) 0.082(4) 0.043(4) 0.006(4) 0.011(3) 0.018(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 Co1 O3 1.908(7) 1_554 ? Co1 O2 1.989(2) . ? Co1 N3 2.036(3) . ? Co1 N1 2.049(3) . ? F1 C16 1.339(4) . ? F2 C16 1.330(4) . ? F3 C16 1.344(4) . ? F4 C17 1.339(4) . ? F5 C17 1.339(4) . ? F6 C17 1.319(4) . ? N1 C20 1.308(4) . ? N1 C18 1.366(4) . ? N2 C20 1.350(4) . ? N2 C19 1.374(4) . ? N2 C21 1.419(4) . ? N3 C25 1.303(4) . ? N3 C27 1.383(5) . ? N4 C25 1.335(4) . ? N4 C26 1.378(5) . ? N4 C28 1.416(4) . ? O1 C1 1.253(4) . ? O2 C1 1.274(4) . ? O3 C15 1.328(11) . ? O3 Co1 1.908(7) 1_556 ? O4 C15 1.218(10) . ? O3' C15' 1.201(10) . ? O4' C15' 1.251(9) . ? S1 C21 1.721(3) . ? S1 C24 1.729(3) . ? S2 C28 1.710(4) . ? S2 C31 1.728(3) . ? C1 C2 1.489(4) . ? C2 C3 1.387(4) . ? C2 C7 1.389(4) . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.387(4) . ? C4 H4 0.9300 . ? C5 C6 1.399(4) . ? C5 C8 1.532(4) . ? C6 C7 1.378(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9' 1.56(2) . ? C8 C16 1.530(4) . ? C8 C17 1.553(4) . ? C8 C9 1.54(2) . ? C9 C10 1.39(2) . ? C9 C14 1.413(19) . ? C10 C11 1.428(15) . ? C10 H10 0.9300 . ? C11 C12 1.358(11) . ? C11 H11 0.9300 . ? C12 C13 1.387(10) . ? C12 C15 1.475(10) . ? C13 C14 1.403(12) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C18 C19 1.353(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.331(4) . ? C22 C23 1.416(5) . ? C22 H22 0.9300 . ? C23 C24 1.355(5) . ? C23 H23 0.9300 . ? C24 C24 1.450(6) 2_875 ? C25 H25 0.9300 . ? C26 C27 1.336(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.342(5) . ? C29 C30 1.412(6) . ? C29 H29 0.9300 . ? C30 C31 1.355(5) . ? C30 H30 0.9300 . ? C31 C31 1.454(7) 2_756 ? C9' C14' 1.369(18) . ? C9' C10' 1.386(19) . ? C10' C11' 1.384(12) . ? C10' H10' 0.9300 . ? C11' C12' 1.405(13) . ? C11' H11' 0.9300 . ? C12' C13' 1.308(15) . ? C12' C15' 1.548(13) . ? C13' C14' 1.402(14) . ? C13' H13' 0.9300 . ? C14' H14' 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Co1 O2 107.6(2) 1_554 . ? O3 Co1 N3 97.3(3) 1_554 . ? O2 Co1 N3 110.46(11) . . ? O3 Co1 N1 112.7(3) 1_554 . ? O2 Co1 N1 115.64(11) . . ? N3 Co1 N1 111.61(11) . . ? C20 N1 C18 105.8(3) . . ? C20 N1 Co1 124.0(2) . . ? C18 N1 Co1 130.2(2) . . ? C20 N2 C19 106.5(3) . . ? C20 N2 C21 125.9(3) . . ? C19 N2 C21 127.5(3) . . ? C25 N3 C27 105.0(3) . . ? C25 N3 Co1 125.5(2) . . ? C27 N3 Co1 129.4(2) . . ? C25 N4 C26 107.0(3) . . ? C25 N4 C28 125.6(3) . . ? C26 N4 C28 127.4(3) . . ? C1 O2 Co1 102.1(2) . . ? C15 O3 Co1 120.7(7) . 1_556 ? C21 S1 C24 91.14(15) . . ? C28 S2 C31 90.76(18) . . ? O1 C1 O2 122.0(3) . . ? O1 C1 C2 119.4(3) . . ? O2 C1 C2 118.5(3) . . ? C3 C2 C7 118.8(3) . . ? C3 C2 C1 120.9(3) . . ? C7 C2 C1 120.3(3) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 117.7(3) . . ? C4 C5 C8 124.0(3) . . ? C6 C5 C8 117.9(2) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 120.4(3) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C9' C8 C16 107.5(6) . . ? C9' C8 C5 116.7(6) . . ? C16 C8 C5 105.7(3) . . ? C9' C8 C17 106.0(8) . . ? C16 C8 C17 108.6(2) . . ? C5 C8 C17 112.0(2) . . ? C16 C8 C9 118.1(7) . . ? C5 C8 C9 106.6(7) . . ? C17 C8 C9 106.0(9) . . ? C10 C9 C14 116.8(16) . . ? C10 C9 C8 123.8(12) . . ? C14 C9 C8 118.6(14) . . ? C9 C10 C11 122.2(10) . . ? C9 C10 H10 118.9 . . ? C11 C10 H10 118.9 . . ? C12 C11 C10 119.4(8) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.8(7) . . ? C11 C12 C15 118.8(8) . . ? C13 C12 C15 121.2(8) . . ? C12 C13 C14 121.5(7) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C9 120.2(11) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O4 C15 O3 124.0(8) . . ? O4 C15 C12 120.1(8) . . ? O3 C15 C12 116.0(8) . . ? F2 C16 F1 106.9(3) . . ? F2 C16 F3 105.6(3) . . ? F1 C16 F3 107.4(3) . . ? F2 C16 C8 112.3(3) . . ? F1 C16 C8 110.5(3) . . ? F3 C16 C8 113.8(3) . . ? F6 C17 F5 107.0(3) . . ? F6 C17 F4 106.6(3) . . ? F5 C17 F4 106.1(3) . . ? F6 C17 C8 111.7(3) . . ? F5 C17 C8 111.7(3) . . ? F4 C17 C8 113.3(3) . . ? C19 C18 N1 109.9(3) . . ? C19 C18 H18 125.0 . . ? N1 C18 H18 125.0 . . ? C18 C19 N2 106.1(3) . . ? C18 C19 H19 127.0 . . ? N2 C19 H19 127.0 . . ? N1 C20 N2 111.7(3) . . ? N1 C20 H20 124.1 . . ? N2 C20 H20 124.1 . . ? C22 C21 N2 128.8(3) . . ? C22 C21 S1 112.7(3) . . ? N2 C21 S1 118.4(2) . . ? C21 C22 C23 111.8(3) . . ? C21 C22 H22 124.1 . . ? C23 C22 H22 124.1 . . ? C24 C23 C22 114.0(3) . . ? C24 C23 H23 123.0 . . ? C22 C23 H23 123.0 . . ? C23 C24 C24 130.2(4) . 2_875 ? C23 C24 S1 110.2(2) . . ? C24 C24 S1 119.7(3) 2_875 . ? N3 C25 N4 112.1(3) . . ? N3 C25 H25 124.0 . . ? N4 C25 H25 124.0 . . ? C27 C26 N4 105.8(3) . . ? C27 C26 H26 127.1 . . ? N4 C26 H26 127.1 . . ? C26 C27 N3 110.2(3) . . ? C26 C27 H27 124.9 . . ? N3 C27 H27 124.9 . . ? C29 C28 N4 128.3(4) . . ? C29 C28 S2 113.5(3) . . ? N4 C28 S2 118.2(3) . . ? C28 C29 C30 111.1(4) . . ? C28 C29 H29 124.4 . . ? C30 C29 H29 124.4 . . ? C31 C30 C29 114.0(4) . . ? C31 C30 H30 123.0 . . ? C29 C30 H30 123.0 . . ? C30 C31 C31 130.7(4) . 2_756 ? C30 C31 S2 110.6(3) . . ? C31 C31 S2 118.7(4) 2_756 . ? C14' C9' C10' 119.1(14) . . ? C14' C9' C8 117.4(12) . . ? C10' C9' C8 123.5(11) . . ? C11' C10' C9' 120.2(10) . . ? C11' C10' H10' 119.9 . . ? C9' C10' H10' 119.9 . . ? C10' C11' C12' 119.1(8) . . ? C10' C11' H11' 120.4 . . ? C12' C11' H11' 120.4 . . ? C13' C12' C11' 120.5(8) . . ? C13' C12' C15' 127.6(10) . . ? C11' C12' C15' 112.0(9) . . ? C12' C13' C14' 121.2(9) . . ? C12' C13' H13' 119.4 . . ? C14' C13' H13' 119.4 . . ? C9' C14' C13' 119.9(11) . . ? C9' C14' H14' 120.0 . . ? C13' C14' H14' 120.0 . . ? O3' C15' O4' 122.5(10) . . ? O3' C15' C12' 114.1(9) . . ? O4' C15' C12' 123.3(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co1 N1 C20 7.3(4) 1_554 . . . ? O2 Co1 N1 C20 -117.0(3) . . . . ? N3 Co1 N1 C20 115.6(3) . . . . ? O3 Co1 N1 C18 -172.6(4) 1_554 . . . ? O2 Co1 N1 C18 63.1(3) . . . . ? N3 Co1 N1 C18 -64.3(3) . . . . ? O3 Co1 N3 C25 175.8(4) 1_554 . . . ? O2 Co1 N3 C25 -72.3(3) . . . . ? N1 Co1 N3 C25 57.8(3) . . . . ? O3 Co1 N3 C27 -9.7(4) 1_554 . . . ? O2 Co1 N3 C27 102.1(3) . . . . ? N1 Co1 N3 C27 -127.8(3) . . . . ? O3 Co1 O2 C1 167.3(3) 1_554 . . . ? N3 Co1 O2 C1 62.1(2) . . . . ? N1 Co1 O2 C1 -65.8(2) . . . . ? Co1 O2 C1 O1 7.1(4) . . . . ? Co1 O2 C1 C2 -170.9(2) . . . . ? O1 C1 C2 C3 161.1(3) . . . . ? O2 C1 C2 C3 -20.8(4) . . . . ? O1 C1 C2 C7 -21.2(4) . . . . ? O2 C1 C2 C7 156.8(3) . . . . ? C7 C2 C3 C4 -0.7(5) . . . . ? C1 C2 C3 C4 177.0(3) . . . . ? C2 C3 C4 C5 -1.2(5) . . . . ? C3 C4 C5 C6 2.1(5) . . . . ? C3 C4 C5 C8 -170.6(3) . . . . ? C4 C5 C6 C7 -1.1(4) . . . . ? C8 C5 C6 C7 172.0(3) . . . . ? C5 C6 C7 C2 -0.7(4) . . . . ? C3 C2 C7 C6 1.6(4) . . . . ? C1 C2 C7 C6 -176.0(3) . . . . ? C4 C5 C8 C9' -151.7(9) . . . . ? C6 C5 C8 C9' 35.6(9) . . . . ? C4 C5 C8 C16 88.9(3) . . . . ? C6 C5 C8 C16 -83.8(3) . . . . ? C4 C5 C8 C17 -29.2(4) . . . . ? C6 C5 C8 C17 158.1(3) . . . . ? C4 C5 C8 C9 -144.7(9) . . . . ? C6 C5 C8 C9 42.6(9) . . . . ? C9' C8 C9 C10 12(6) . . . . ? C16 C8 C9 C10 -19(2) . . . . ? C5 C8 C9 C10 -137.1(15) . . . . ? C17 C8 C9 C10 103.4(17) . . . . ? C9' C8 C9 C14 -158(9) . . . . ? C16 C8 C9 C14 171.4(11) . . . . ? C5 C8 C9 C14 52.8(17) . . . . ? C17 C8 C9 C14 -66.7(16) . . . . ? C14 C9 C10 C11 -4(2) . . . . ? C8 C9 C10 C11 -174.3(13) . . . . ? C9 C10 C11 C12 4.2(18) . . . . ? C10 C11 C12 C13 -2.0(14) . . . . ? C10 C11 C12 C15 174.3(9) . . . . ? C11 C12 C13 C14 0.1(13) . . . . ? C15 C12 C13 C14 -176.1(8) . . . . ? C12 C13 C14 C9 -0.1(17) . . . . ? C10 C9 C14 C13 2(2) . . . . ? C8 C9 C14 C13 172.8(11) . . . . ? Co1 O3 C15 O4 4.4(12) 1_556 . . . ? Co1 O3 C15 C12 -176.3(6) 1_556 . . . ? C11 C12 C15 O4 -152.6(9) . . . . ? C13 C12 C15 O4 23.7(12) . . . . ? C11 C12 C15 O3 28.1(11) . . . . ? C13 C12 C15 O3 -155.6(8) . . . . ? C9' C8 C16 F2 -175.3(7) . . . . ? C5 C8 C16 F2 -49.9(3) . . . . ? C17 C8 C16 F2 70.4(3) . . . . ? C9 C8 C16 F2 -168.9(9) . . . . ? C9' C8 C16 F1 -56.0(8) . . . . ? C5 C8 C16 F1 69.3(3) . . . . ? C17 C8 C16 F1 -170.3(3) . . . . ? C9 C8 C16 F1 -49.7(10) . . . . ? C9' C8 C16 F3 64.8(8) . . . . ? C5 C8 C16 F3 -169.8(3) . . . . ? C17 C8 C16 F3 -49.5(4) . . . . ? C9 C8 C16 F3 71.2(9) . . . . ? C9' C8 C17 F6 79.0(6) . . . . ? C16 C8 C17 F6 -165.7(3) . . . . ? C5 C8 C17 F6 -49.4(3) . . . . ? C9 C8 C17 F6 66.4(7) . . . . ? C9' C8 C17 F5 -40.8(6) . . . . ? C16 C8 C17 F5 74.5(3) . . . . ? C5 C8 C17 F5 -169.2(2) . . . . ? C9 C8 C17 F5 -53.3(7) . . . . ? C9' C8 C17 F4 -160.6(6) . . . . ? C16 C8 C17 F4 -45.3(4) . . . . ? C5 C8 C17 F4 71.0(3) . . . . ? C9 C8 C17 F4 -173.1(6) . . . . ? C20 N1 C18 C19 -0.1(4) . . . . ? Co1 N1 C18 C19 179.8(3) . . . . ? N1 C18 C19 N2 0.2(4) . . . . ? C20 N2 C19 C18 -0.2(4) . . . . ? C21 N2 C19 C18 177.1(3) . . . . ? C18 N1 C20 N2 0.0(4) . . . . ? Co1 N1 C20 N2 -179.9(2) . . . . ? C19 N2 C20 N1 0.1(4) . . . . ? C21 N2 C20 N1 -177.2(3) . . . . ? C20 N2 C21 C22 -146.7(4) . . . . ? C19 N2 C21 C22 36.5(6) . . . . ? C20 N2 C21 S1 36.3(5) . . . . ? C19 N2 C21 S1 -140.5(3) . . . . ? C24 S1 C21 C22 3.1(3) . . . . ? C24 S1 C21 N2 -179.4(3) . . . . ? N2 C21 C22 C23 -179.7(3) . . . . ? S1 C21 C22 C23 -2.6(4) . . . . ? C21 C22 C23 C24 0.4(5) . . . . ? C22 C23 C24 C24 -177.7(4) . . . 2_875 ? C22 C23 C24 S1 1.9(4) . . . . ? C21 S1 C24 C23 -2.8(3) . . . . ? C21 S1 C24 C24 176.9(4) . . . 2_875 ? C27 N3 C25 N4 -0.6(4) . . . . ? Co1 N3 C25 N4 175.0(2) . . . . ? C26 N4 C25 N3 0.0(4) . . . . ? C28 N4 C25 N3 -178.6(3) . . . . ? C25 N4 C26 C27 0.5(5) . . . . ? C28 N4 C26 C27 179.2(4) . . . . ? N4 C26 C27 N3 -0.9(5) . . . . ? C25 N3 C27 C26 0.9(5) . . . . ? Co1 N3 C27 C26 -174.4(3) . . . . ? C25 N4 C28 C29 -137.0(4) . . . . ? C26 N4 C28 C29 44.6(6) . . . . ? C25 N4 C28 S2 41.9(4) . . . . ? C26 N4 C28 S2 -136.5(3) . . . . ? C31 S2 C28 C29 1.2(3) . . . . ? C31 S2 C28 N4 -177.9(3) . . . . ? N4 C28 C29 C30 177.9(4) . . . . ? S2 C28 C29 C30 -1.1(5) . . . . ? C28 C29 C30 C31 0.3(5) . . . . ? C29 C30 C31 C31 -178.7(4) . . . 2_756 ? C29 C30 C31 S2 0.6(5) . . . . ? C28 S2 C31 C30 -1.0(3) . . . . ? C28 S2 C31 C31 178.4(4) . . . 2_756 ? C16 C8 C9' C14' 160.5(12) . . . . ? C5 C8 C9' C14' 42.1(17) . . . . ? C17 C8 C9' C14' -83.5(14) . . . . ? C9 C8 C9' C14' 8(6) . . . . ? C16 C8 C9' C10' -15.8(17) . . . . ? C5 C8 C9' C10' -134.2(13) . . . . ? C17 C8 C9' C10' 100.2(15) . . . . ? C9 C8 C9' C10' -168(9) . . . . ? C14' C9' C10' C11' 2(2) . . . . ? C8 C9' C10' C11' 178.5(12) . . . . ? C9' C10' C11' C12' -1.0(17) . . . . ? C10' C11' C12' C13' 0.2(14) . . . . ? C10' C11' C12' C15' 178.7(8) . . . . ? C11' C12' C13' C14' -0.7(15) . . . . ? C15' C12' C13' C14' -178.9(9) . . . . ? C10' C9' C14' C13' -3(2) . . . . ? C8 C9' C14' C13' -179.2(11) . . . . ? C12' C13' C14' C9' 2.0(18) . . . . ? C13' C12' C15' O3' -0.7(15) . . . . ? C11' C12' C15' O3' -179.1(9) . . . . ? C13' C12' C15' O4' 176.8(10) . . . . ? C11' C12' C15' O4' -1.5(13) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.522 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 963192' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C88 H56 N16 O16 S8 Zn4' _chemical_formula_sum 'C88 H56 N16 O16 S8 Zn4' _chemical_formula_weight 2111.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.8224(12) _cell_length_b 27.2700(19) _cell_length_c 18.3256(12) _cell_angle_alpha 90.00 _cell_angle_beta 110.5320(10) _cell_angle_gamma 90.00 _cell_volume 8340.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7241 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.04 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4288 _exptl_absorpt_coefficient_mu 1.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6922 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55045 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0945 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 27.10 _reflns_number_total 18395 _reflns_number_gt 9343 _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^)+(0.0350P)^2^+0.0500P] 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 18395 _refine_ls_number_parameters 1189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6885(2) 0.41243(15) 0.0740(2) 0.0468(12) Uani 1 1 d . . . H1 H 0.7062 0.3816 0.0653 0.056 Uiso 1 1 calc R . . C2 C 0.6499(2) 0.44528(16) 0.0170(2) 0.0457(11) Uani 1 1 d . . . H2 H 0.6366 0.4415 -0.0365 0.055 Uiso 1 1 calc R . . C3 C 0.6659(2) 0.47541(16) 0.1316(2) 0.0423(11) Uani 1 1 d . . . H3 H 0.6656 0.4970 0.1709 0.051 Uiso 1 1 calc R . . C4 C 0.5913(3) 0.52838(16) 0.0205(2) 0.0461(11) Uani 1 1 d . . . C5 C 0.5775(2) 0.54326(15) -0.0528(2) 0.0445(11) Uani 1 1 d . . . H5 H 0.5955 0.5276 -0.0887 0.053 Uiso 1 1 calc R . . C6 C 0.5301(3) 0.58753(15) -0.0669(2) 0.0501(12) Uani 1 1 d . . . H6 H 0.5136 0.6041 -0.1143 0.060 Uiso 1 1 calc R . . C7 C 0.5118(2) 0.60280(15) -0.0049(2) 0.0428(11) Uani 1 1 d . . . C8 C 0.4663(3) 0.64544(16) 0.0026(2) 0.0451(12) Uani 1 1 d . . . C9 C 0.4507(2) 0.66358(16) 0.0653(2) 0.0504(12) Uani 1 1 d . . . H9 H 0.4680 0.6481 0.1137 0.061 Uiso 1 1 calc R . . C10 C 0.4057(2) 0.70813(15) 0.0508(2) 0.0465(12) Uani 1 1 d . . . H10 H 0.3937 0.7260 0.0885 0.056 Uiso 1 1 calc R . . C11 C 0.3834(3) 0.72045(16) -0.0234(2) 0.0448(12) Uani 1 1 d . . . C12 C 0.3158(3) 0.77465(15) -0.1325(2) 0.0470(12) Uani 1 1 d . . . H12 H 0.3261 0.7557 -0.1701 0.056 Uiso 1 1 calc R . . C13 C 0.3085(3) 0.79700(15) -0.0233(3) 0.0493(12) Uani 1 1 d . . . H13 H 0.3140 0.7977 0.0291 0.059 Uiso 1 1 calc R . . C14 C 0.2699(2) 0.83065(15) -0.0785(2) 0.0452(11) Uani 1 1 d . . . H14 H 0.2429 0.8581 -0.0704 0.054 Uiso 1 1 calc R . . C15 C -0.1803(2) 0.75932(15) -0.1421(2) 0.0421(11) Uani 1 1 d . . . H15 H -0.1681 0.7404 -0.1787 0.051 Uiso 1 1 calc R . . C16 C -0.2250(2) 0.81587(17) -0.0907(2) 0.0501(12) Uani 1 1 d . . . H16 H -0.2494 0.8450 -0.0846 0.060 Uiso 1 1 calc R . . C17 C -0.1928(3) 0.78394(16) -0.0320(3) 0.0470(12) Uani 1 1 d . . . H17 H -0.1918 0.7858 0.0190 0.056 Uiso 1 1 calc R . . C18 C -0.1185(2) 0.70613(16) -0.0299(2) 0.0433(11) Uani 1 1 d . . . C19 C -0.1136(3) 0.68679(14) 0.0393(2) 0.0457(11) Uani 1 1 d . . . H19 H -0.1427 0.6985 0.0690 0.055 Uiso 1 1 calc R . . C20 C -0.0605(2) 0.64745(16) 0.0617(2) 0.0481(12) Uani 1 1 d . . . H20 H -0.0471 0.6320 0.1099 0.058 Uiso 1 1 calc R . . C21 C -0.0300(2) 0.63379(15) 0.0060(2) 0.0415(11) Uani 1 1 d . . . C22 C 0.0210(3) 0.59311(15) 0.0043(2) 0.0441(11) Uani 1 1 d . . . C23 C 0.0560(2) 0.58161(16) -0.0471(2) 0.0499(12) Uani 1 1 d . . . H23 H 0.0472 0.5995 -0.0925 0.060 Uiso 1 1 calc R . . C24 C 0.1074(3) 0.54034(16) -0.0277(2) 0.0524(13) Uani 1 1 d . . . H24 H 0.1377 0.5296 -0.0569 0.063 Uiso 1 1 calc R . . C25 C 0.1070(2) 0.51866(16) 0.0373(2) 0.0446(11) Uani 1 1 d . . . C26 C 0.1608(2) 0.46218(15) 0.1446(2) 0.0453(12) Uani 1 1 d . . . H26 H 0.1445 0.4790 0.1806 0.054 Uiso 1 1 calc R . . C27 C 0.1807(3) 0.44358(15) 0.0388(2) 0.0486(12) Uani 1 1 d . . . H27 H 0.1814 0.4448 -0.0117 0.058 Uiso 1 1 calc R . . C28 C 0.2116(2) 0.40777(17) 0.0924(2) 0.0512(12) Uani 1 1 d . . . H28 H 0.2371 0.3796 0.0846 0.061 Uiso 1 1 calc R . . C29 C 0.1572(2) 0.77483(14) -0.3597(2) 0.0408(11) Uani 1 1 d . . . H29 H 0.1387 0.7591 -0.3243 0.049 Uiso 1 1 calc R . . C30 C 0.2204(2) 0.82427(15) -0.4076(2) 0.0454(11) Uani 1 1 d . . . H30 H 0.2529 0.8497 -0.4127 0.055 Uiso 1 1 calc R . . C31 C 0.1866(2) 0.78864(15) -0.4630(2) 0.0459(12) Uani 1 1 d . . . H31 H 0.1911 0.7858 -0.5118 0.055 Uiso 1 1 calc R . . C32 C 0.1010(2) 0.71778(15) -0.4664(2) 0.0405(11) Uani 1 1 d . . . C33 C 0.0791(3) 0.70394(16) -0.5429(2) 0.0485(12) Uani 1 1 d . . . H33 H 0.0949 0.7196 -0.5802 0.058 Uiso 1 1 calc R . . C34 C 0.0284(3) 0.66193(16) -0.5566(3) 0.0514(12) Uani 1 1 d . . . H34 H 0.0024 0.6500 -0.6067 0.062 Uiso 1 1 calc R . . C35 C 0.0197(2) 0.64033(15) -0.4940(2) 0.0440(12) Uani 1 1 d . . . C36 C -0.3312(2) 0.76289(15) -0.3673(2) 0.0397(11) Uani 1 1 d . . . H36 H -0.3380 0.7446 -0.3272 0.048 Uiso 1 1 calc R . . C37 C -0.3028(3) 0.81835(17) -0.4284(3) 0.0518(12) Uani 1 1 d . . . H37 H -0.2825 0.8480 -0.4385 0.062 Uiso 1 1 calc R . . C38 C -0.3404(3) 0.78732(16) -0.4819(3) 0.0502(12) Uani 1 1 d . . . H38 H -0.3526 0.7906 -0.5353 0.060 Uiso 1 1 calc R . . C39 C 0.3167(2) 0.45862(16) 0.3700(2) 0.0423(11) Uani 1 1 d . . . H39 H 0.3329 0.4741 0.3327 0.051 Uiso 1 1 calc R . . C40 C 0.2655(3) 0.40759(17) 0.4243(2) 0.0488(12) Uani 1 1 d . . . H40 H 0.2367 0.3809 0.4321 0.059 Uiso 1 1 calc R . . C41 C 0.3047(3) 0.44009(16) 0.4787(3) 0.0501(12) Uani 1 1 d . . . H41 H 0.3103 0.4395 0.5311 0.060 Uiso 1 1 calc R . . C42 C 0.3830(3) 0.51670(17) 0.4774(2) 0.0456(12) Uani 1 1 d . . . C43 C 0.4076(3) 0.52767(15) 0.5526(2) 0.0470(12) Uani 1 1 d . . . H43 H 0.3934 0.5113 0.5903 0.056 Uiso 1 1 calc R . . C44 C 0.4587(3) 0.56815(16) 0.5655(2) 0.0490(12) Uani 1 1 d . . . H44 H 0.4852 0.5804 0.6153 0.059 Uiso 1 1 calc R . . C45 C 0.4674(2) 0.58802(16) 0.5036(2) 0.0452(12) Uani 1 1 d . . . C46 C 0.5138(3) 0.63237(16) 0.4955(2) 0.0456(12) Uani 1 1 d . . . C47 C 0.5265(3) 0.64951(15) 0.4329(2) 0.0470(12) Uani 1 1 d . . . H47 H 0.5022 0.6366 0.3831 0.056 Uiso 1 1 calc R . . C48 C 0.5792(3) 0.68826(17) 0.4491(2) 0.0556(13) Uani 1 1 d . . . H48 H 0.6002 0.7016 0.4136 0.067 Uiso 1 1 calc R . . C49 C 0.5967(3) 0.70436(15) 0.5221(2) 0.0435(11) Uani 1 1 d . . . C50 C 0.8233(2) 0.47249(15) 0.3614(2) 0.0424(11) Uani 1 1 d . . . H50 H 0.8393 0.4899 0.3257 0.051 Uiso 1 1 calc R . . C51 C 0.7686(2) 0.41873(15) 0.4106(2) 0.0451(11) Uani 1 1 d . . . H51 H 0.7402 0.3912 0.4160 0.054 Uiso 1 1 calc R . . C52 C 0.8052(3) 0.45159(15) 0.4683(2) 0.0479(12) Uani 1 1 d . . . H52 H 0.8054 0.4511 0.5191 0.057 Uiso 1 1 calc R . . C53 C 0.8907(2) 0.52592(15) 0.4755(2) 0.0395(10) Uani 1 1 d . . . C54 C 0.9141(2) 0.53487(15) 0.5509(2) 0.0476(12) Uani 1 1 d . . . H54 H 0.9011 0.5160 0.5870 0.057 Uiso 1 1 calc R . . C55 C 0.9636(3) 0.57903(15) 0.5690(2) 0.0494(12) Uani 1 1 d . . . H55 H 0.9853 0.5918 0.6192 0.059 Uiso 1 1 calc R . . C56 C 0.9753(2) 0.59968(15) 0.5076(2) 0.0395(11) Uani 1 1 d . . . C57 C 0.6567(3) 0.30239(19) 0.2830(3) 0.0536(13) Uani 1 1 d . . . C58 C 0.5734(3) 0.28811(19) 0.2703(2) 0.0499(12) Uani 1 1 d . . . C59 C 0.5497(3) 0.23890(16) 0.2546(2) 0.0458(12) Uani 1 1 d . . . H59 H 0.5877 0.2148 0.2576 0.055 Uiso 1 1 calc R . . C60 C 0.4710(3) 0.22654(17) 0.2349(2) 0.0495(12) Uani 1 1 d . . . H60 H 0.4561 0.1939 0.2248 0.059 Uiso 1 1 calc R . . C61 C 0.4156(3) 0.25930(15) 0.2299(2) 0.0412(11) Uani 1 1 d . . . H61 H 0.3626 0.2492 0.2165 0.049 Uiso 1 1 calc R . . C62 C 0.4341(3) 0.30967(16) 0.2444(2) 0.0430(11) Uani 1 1 d . . . C63 C 0.5132(2) 0.32340(15) 0.2641(2) 0.0384(10) Uani 1 1 d . . . H63 H 0.5272 0.3563 0.2734 0.046 Uiso 1 1 calc R . . C64 C 0.3724(3) 0.34526(18) 0.2432(2) 0.0432(11) Uani 1 1 d . . . C65 C 0.1246(3) 0.90995(18) -0.2048(3) 0.0545(13) Uani 1 1 d . . . C66 C 0.0498(3) 0.94086(18) -0.2262(2) 0.0514(13) Uani 1 1 d . . . C67 C 0.0544(3) 0.99197(17) -0.2292(2) 0.0489(12) Uani 1 1 d . . . H67 H 0.1043 1.0071 -0.2126 0.059 Uiso 1 1 calc R . . C68 C -0.0129(3) 1.01995(16) -0.2561(2) 0.0492(12) Uani 1 1 d . . . H68 H -0.0088 1.0539 -0.2564 0.059 Uiso 1 1 calc R . . C69 C -0.0882(3) 0.99748(14) -0.2833(2) 0.0405(11) Uani 1 1 d . . . H69 H -0.1346 1.0163 -0.3018 0.049 Uiso 1 1 calc R . . C70 C -0.0930(3) 0.94698(15) -0.2825(2) 0.0419(11) Uani 1 1 d . . . C71 C -0.0243(3) 0.91880(17) -0.2547(2) 0.0494(12) Uani 1 1 d . . . H71 H -0.0282 0.8848 -0.2553 0.059 Uiso 1 1 calc R . . C72 C -0.1741(3) 0.92328(17) -0.3071(3) 0.0540(13) Uani 1 1 d . . . C73 C 0.8438(3) 0.32936(16) 0.2063(2) 0.0423(11) Uani 1 1 d . . . C74 C 0.9139(3) 0.29836(15) 0.2241(2) 0.0405(11) Uani 1 1 d . . . C75 C 0.9897(2) 0.31622(15) 0.2521(2) 0.0394(10) Uani 1 1 d . . . H75 H 0.9985 0.3499 0.2559 0.047 Uiso 1 1 calc R . . C76 C 1.0538(3) 0.28410(18) 0.2750(2) 0.0501(12) Uani 1 1 d . . . C77 C 1.0402(3) 0.23354(16) 0.2702(2) 0.0491(13) Uani 1 1 d . . . H77 H 1.0833 0.2119 0.2859 0.059 Uiso 1 1 calc R . . C78 C 0.9627(3) 0.21572(18) 0.2422(2) 0.0555(13) Uani 1 1 d . . . H78 H 0.9538 0.1821 0.2395 0.067 Uiso 1 1 calc R . . C79 C 0.8996(3) 0.24710(16) 0.2187(2) 0.0471(12) Uani 1 1 d . . . H79 H 0.8474 0.2351 0.1992 0.056 Uiso 1 1 calc R . . C80 C 1.1371(3) 0.30385(17) 0.3009(3) 0.0481(12) Uani 1 1 d . . . C81 C 0.3425(3) 0.91545(18) -0.2677(2) 0.0500(12) Uani 1 1 d . . . C82 C 0.4213(3) 0.93918(15) -0.2609(2) 0.0424(11) Uani 1 1 d . . . C83 C 0.4353(3) 0.99028(15) -0.2615(2) 0.0422(11) Uani 1 1 d . . . H83 H 0.3924 1.0119 -0.2721 0.051 Uiso 1 1 calc R . . C84 C 0.5094(3) 1.00812(16) -0.2472(2) 0.0449(11) Uani 1 1 d . . . H84 H 0.5172 1.0419 -0.2459 0.054 Uiso 1 1 calc R . . C85 C 0.5764(3) 0.97627(19) -0.2339(2) 0.0511(13) Uani 1 1 d . . . H85 H 0.6276 0.9888 -0.2236 0.061 Uiso 1 1 calc R . . C86 C 0.5631(3) 0.92609(19) -0.2368(2) 0.0525(13) Uani 1 1 d . . . C87 C 0.4873(3) 0.91031(16) -0.2510(2) 0.0442(11) Uani 1 1 d . . . H87 H 0.4791 0.8766 -0.2543 0.053 Uiso 1 1 calc R . . C88 C 0.6291(3) 0.89072(17) -0.2329(3) 0.0494(12) Uani 1 1 d . . . N1 N 0.69746(19) 0.43091(12) 0.14454(19) 0.0421(9) Uani 1 1 d . . . N2 N 0.6345(2) 0.48565(13) 0.0561(2) 0.0420(9) Uani 1 1 d . . . N3 N 0.3375(2) 0.76217(12) -0.0596(2) 0.0406(9) Uani 1 1 d . . . N4 N 0.2771(2) 0.81762(12) -0.14782(19) 0.0439(9) Uani 1 1 d . . . N5 N -0.21893(19) 0.80198(12) -0.15907(19) 0.0421(9) Uani 1 1 d . . . N6 N -0.1606(2) 0.74636(13) -0.0671(2) 0.0423(9) Uani 1 1 d . . . N7 N 0.1996(2) 0.41954(13) 0.15850(18) 0.0442(9) Uani 1 1 d . . . N8 N 0.1487(2) 0.47726(13) 0.07403(19) 0.0448(9) Uani 1 1 d . . . N9 N 0.1990(2) 0.81655(12) -0.34504(18) 0.0425(9) Uani 1 1 d . . . N10 N 0.1454(2) 0.75853(12) -0.43145(19) 0.0388(9) Uani 1 1 d . . . N11 N 0.78009(19) 0.43272(12) 0.34332(19) 0.0424(9) Uani 1 1 d . . . N12 N 0.8425(2) 0.48614(12) 0.43595(19) 0.0413(9) Uani 1 1 d . . . N13 N -0.2961(2) 0.80319(13) -0.35544(19) 0.0411(9) Uani 1 1 d . . . N14 N -0.3590(2) 0.74731(14) -0.4425(2) 0.0434(9) Uani 1 1 d . . . N15 N 0.2742(2) 0.41936(13) 0.35633(19) 0.0435(9) Uani 1 1 d . . . N16 N 0.3352(2) 0.47492(14) 0.4419(2) 0.0457(10) Uani 1 1 d . . . O1 O 0.85388(14) 0.36984(9) 0.24386(14) 0.0317(6) Uani 1 1 d . . . O2 O 0.77810(17) 0.32125(10) 0.15312(15) 0.0469(7) Uani 1 1 d . . . O3 O 1.19057(17) 0.28156(11) 0.35582(16) 0.0578(8) Uani 1 1 d . . . O4 O 1.14502(16) 0.34146(11) 0.26939(16) 0.0507(8) Uani 1 1 d . . . O5 O 0.70981(18) 0.27128(11) 0.28314(16) 0.0569(9) Uani 1 1 d . . . O6 O 0.67277(17) 0.34647(12) 0.29316(16) 0.0536(8) Uani 1 1 d . . . O7 O 0.39471(16) 0.38522(10) 0.27616(17) 0.0502(8) Uani 1 1 d . . . O8 O 0.30238(16) 0.33104(10) 0.21254(16) 0.0459(7) Uani 1 1 d . . . O9 O 0.18179(18) 0.92177(11) -0.15221(17) 0.0556(8) Uani 1 1 d . . . O10 O 0.11543(15) 0.86929(10) -0.24392(14) 0.0411(7) Uani 1 1 d . . . O11 O -0.23598(19) 0.95135(11) -0.33019(16) 0.0619(9) Uani 1 1 d . . . O12 O -0.17146(15) 0.87876(10) -0.29904(15) 0.0397(7) Uani 1 1 d . . . O13 O 0.34522(15) 0.87032(10) -0.25765(14) 0.0385(7) Uani 1 1 d . . . O14 O 0.28613(18) 0.94049(11) -0.27798(16) 0.0521(8) Uani 1 1 d . . . O15 O 0.69363(17) 0.89933(10) -0.19202(16) 0.0442(8) Uani 1 1 d . . . O16 O 0.61047(15) 0.85198(10) -0.27300(15) 0.0403(7) Uani 1 1 d . . . S1 S -0.06417(7) 0.67197(4) -0.07255(6) 0.0474(3) Uani 1 1 d . . . S2 S 0.04678(7) 0.54981(4) 0.07707(6) 0.0481(3) Uani 1 1 d . . . S3 S 0.54864(7) 0.56318(4) 0.07169(6) 0.0443(3) Uani 1 1 d . . . S4 S 0.41989(7) 0.68232(4) -0.07702(6) 0.0446(3) Uani 1 1 d . . . S5 S 0.92402(7) 0.56588(4) 0.42433(6) 0.0433(3) Uani 1 1 d . . . S6 S 0.06118(7) 0.67873(4) -0.41854(6) 0.0456(3) Uani 1 1 d . . . S7 S 0.55607(7) 0.66844(4) 0.57396(6) 0.0477(3) Uani 1 1 d . . . S8 S 0.41625(7) 0.55417(4) 0.42309(6) 0.0479(3) Uani 1 1 d . . . Zn1 Zn 0.74179(3) 0.391500(17) 0.24472(2) 0.03297(13) Uani 1 1 d . . . Zn2 Zn 0.23694(3) 0.857400(17) -0.24572(3) 0.03416(13) Uani 1 1 d . . . Zn3 Zn -0.25425(3) 0.843212(18) -0.25707(2) 0.03595(13) Uani 1 1 d . . . Zn4 Zn 0.23477(3) 0.378303(18) 0.25753(3) 0.03594(13) 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 C1 0.060(3) 0.036(3) 0.046(3) -0.014(2) 0.021(2) 0.011(2) C2 0.050(3) 0.049(3) 0.033(3) -0.006(2) 0.008(2) 0.006(2) C3 0.047(3) 0.041(3) 0.037(3) 0.011(2) 0.012(2) 0.006(2) C4 0.044(3) 0.051(3) 0.040(3) 0.003(2) 0.010(2) 0.009(2) C5 0.037(3) 0.046(3) 0.046(3) 0.001(2) 0.008(2) 0.014(2) C6 0.064(3) 0.044(3) 0.039(3) 0.009(2) 0.014(2) 0.008(2) C7 0.053(3) 0.031(3) 0.044(3) 0.001(2) 0.015(2) 0.018(2) C8 0.043(3) 0.046(3) 0.041(3) 0.013(2) 0.008(2) 0.017(2) C9 0.046(3) 0.053(3) 0.046(3) 0.012(2) 0.009(2) 0.023(2) C10 0.055(3) 0.044(3) 0.034(3) 0.009(2) 0.007(2) 0.007(2) C11 0.045(3) 0.045(3) 0.039(3) 0.012(2) 0.009(2) 0.015(2) C12 0.055(3) 0.044(3) 0.043(3) 0.014(2) 0.019(2) 0.014(2) C13 0.053(3) 0.050(3) 0.047(3) 0.016(2) 0.019(2) 0.020(2) C14 0.053(3) 0.030(3) 0.045(3) 0.009(2) 0.008(2) 0.008(2) C15 0.034(3) 0.050(3) 0.038(3) 0.007(2) 0.007(2) 0.011(2) C16 0.043(3) 0.058(3) 0.044(3) 0.012(2) 0.009(2) 0.019(2) C17 0.049(3) 0.048(3) 0.047(3) 0.011(2) 0.021(2) 0.010(2) C18 0.038(3) 0.049(3) 0.040(3) -0.004(2) 0.010(2) 0.011(2) C19 0.055(3) 0.035(3) 0.051(3) 0.005(2) 0.023(2) 0.007(2) C20 0.045(3) 0.050(3) 0.050(3) 0.012(2) 0.018(2) 0.011(2) C21 0.039(3) 0.047(3) 0.033(3) 0.006(2) 0.006(2) 0.014(2) C22 0.051(3) 0.046(3) 0.028(2) -0.003(2) 0.004(2) 0.002(2) C23 0.039(3) 0.058(3) 0.046(3) 0.012(2) 0.008(2) 0.013(2) C24 0.055(3) 0.054(3) 0.047(3) 0.012(2) 0.016(2) 0.023(2) C25 0.041(3) 0.053(3) 0.037(3) 0.007(2) 0.010(2) -0.007(2) C26 0.043(3) 0.049(3) 0.038(3) 0.015(2) 0.006(2) 0.019(2) C27 0.053(3) 0.048(3) 0.044(3) 0.011(2) 0.016(2) 0.021(2) C28 0.046(3) 0.059(3) 0.039(3) 0.015(2) 0.002(2) 0.022(2) C29 0.038(3) 0.032(3) 0.048(3) 0.012(2) 0.009(2) -0.013(2) C30 0.049(3) 0.033(3) 0.052(3) -0.012(2) 0.014(2) -0.004(2) C31 0.052(3) 0.040(3) 0.049(3) -0.016(2) 0.022(2) -0.014(2) C32 0.046(3) 0.035(3) 0.039(3) -0.009(2) 0.013(2) -0.013(2) C33 0.058(3) 0.047(3) 0.035(3) -0.012(2) 0.010(2) -0.010(2) C34 0.058(3) 0.042(3) 0.056(3) -0.015(2) 0.023(3) -0.009(2) C35 0.046(3) 0.037(3) 0.046(3) -0.014(2) 0.012(2) -0.011(2) C36 0.032(3) 0.042(3) 0.043(3) 0.004(2) 0.011(2) 0.013(2) C37 0.057(3) 0.052(3) 0.047(3) 0.010(3) 0.019(3) 0.004(3) C38 0.055(3) 0.048(3) 0.039(3) 0.008(2) 0.006(2) 0.008(2) C39 0.036(3) 0.049(3) 0.039(3) 0.016(2) 0.009(2) 0.000(2) C40 0.049(3) 0.052(3) 0.039(3) 0.007(2) 0.006(2) 0.005(2) C41 0.049(3) 0.049(3) 0.056(3) 0.012(3) 0.024(3) 0.012(2) C42 0.040(3) 0.058(3) 0.036(3) 0.010(2) 0.009(2) 0.010(2) C43 0.055(3) 0.042(3) 0.044(3) 0.008(2) 0.017(2) -0.016(2) C44 0.053(3) 0.046(3) 0.045(3) -0.012(2) 0.014(2) -0.012(2) C45 0.034(3) 0.060(3) 0.038(3) 0.014(2) 0.008(2) 0.011(2) C46 0.048(3) 0.051(3) 0.034(3) 0.007(2) 0.009(2) 0.016(2) C47 0.056(3) 0.048(3) 0.032(3) -0.007(2) 0.009(2) -0.016(2) C48 0.056(3) 0.064(4) 0.042(3) 0.007(3) 0.012(2) -0.012(3) C49 0.055(3) 0.037(3) 0.032(3) 0.005(2) 0.008(2) 0.014(2) C50 0.045(3) 0.039(3) 0.042(3) -0.005(2) 0.014(2) -0.005(2) C51 0.054(3) 0.031(3) 0.050(3) -0.018(2) 0.018(2) -0.008(2) C52 0.052(3) 0.050(3) 0.042(3) -0.015(2) 0.017(2) -0.019(2) C53 0.042(3) 0.037(3) 0.035(3) -0.002(2) 0.007(2) 0.005(2) C54 0.055(3) 0.039(3) 0.038(3) -0.009(2) 0.003(2) -0.016(2) C55 0.060(3) 0.041(3) 0.044(3) -0.014(2) 0.013(2) -0.020(2) C56 0.042(3) 0.033(3) 0.042(3) -0.012(2) 0.013(2) -0.010(2) C57 0.054(4) 0.061(4) 0.046(3) 0.010(3) 0.017(3) -0.003(3) C58 0.025(3) 0.074(4) 0.044(3) -0.001(3) 0.003(2) 0.008(3) C59 0.054(3) 0.046(3) 0.040(3) 0.013(2) 0.021(2) 0.018(2) C60 0.056(4) 0.046(3) 0.047(3) -0.004(2) 0.019(3) -0.011(3) C61 0.048(3) 0.030(3) 0.046(3) -0.004(2) 0.017(2) -0.010(2) C62 0.038(3) 0.048(3) 0.038(3) 0.008(2) 0.006(2) -0.017(2) C63 0.034(3) 0.041(3) 0.040(3) -0.007(2) 0.012(2) -0.005(2) C64 0.035(3) 0.056(3) 0.037(3) 0.000(2) 0.011(2) -0.012(2) C65 0.052(3) 0.061(4) 0.035(3) -0.002(3) -0.003(2) 0.024(3) C66 0.057(3) 0.055(3) 0.035(3) 0.009(2) 0.006(2) 0.028(3) C67 0.045(3) 0.058(3) 0.043(3) 0.004(2) 0.015(2) 0.013(2) C68 0.055(3) 0.037(3) 0.053(3) 0.012(2) 0.015(2) 0.011(2) C69 0.053(3) 0.024(2) 0.048(3) 0.013(2) 0.022(2) 0.017(2) C70 0.050(3) 0.031(3) 0.045(3) 0.013(2) 0.017(2) 0.016(2) C71 0.058(3) 0.046(3) 0.043(3) -0.003(2) 0.017(3) 0.008(2) C72 0.066(4) 0.038(3) 0.056(3) -0.002(3) 0.018(3) 0.017(3) C73 0.034(3) 0.046(3) 0.044(3) -0.018(2) 0.010(2) -0.002(2) C74 0.040(3) 0.038(3) 0.043(3) 0.012(2) 0.013(2) 0.006(2) C75 0.029(2) 0.043(3) 0.047(3) 0.007(2) 0.013(2) 0.002(2) C76 0.037(3) 0.063(4) 0.046(3) 0.019(2) 0.009(2) 0.011(2) C77 0.052(3) 0.044(3) 0.047(3) 0.008(2) 0.011(2) 0.022(2) C78 0.065(4) 0.055(3) 0.046(3) 0.014(2) 0.020(3) 0.012(3) C79 0.059(3) 0.040(3) 0.042(3) 0.003(2) 0.017(2) 0.006(2) C80 0.046(3) 0.054(3) 0.043(3) 0.013(2) 0.013(2) 0.015(2) C81 0.059(4) 0.044(3) 0.032(3) -0.007(2) -0.003(2) -0.007(3) C82 0.049(3) 0.038(3) 0.033(2) -0.013(2) 0.005(2) -0.009(2) C83 0.044(3) 0.041(3) 0.040(3) 0.011(2) 0.012(2) 0.012(2) C84 0.059(3) 0.040(3) 0.029(2) -0.006(2) 0.007(2) 0.005(2) C85 0.026(3) 0.074(4) 0.047(3) 0.014(3) 0.006(2) -0.006(3) C86 0.051(3) 0.064(4) 0.039(3) 0.014(2) 0.010(2) 0.023(3) C87 0.049(3) 0.045(3) 0.038(3) -0.005(2) 0.015(2) 0.003(2) C88 0.042(3) 0.052(3) 0.040(3) -0.009(2) -0.004(2) -0.004(3) N1 0.040(2) 0.040(2) 0.047(2) 0.0060(18) 0.0168(18) 0.0116(18) N2 0.040(2) 0.040(2) 0.043(2) 0.0095(19) 0.0118(18) 0.0115(18) N3 0.049(3) 0.034(2) 0.038(2) 0.0068(18) 0.0154(19) 0.0118(17) N4 0.050(2) 0.037(2) 0.041(2) 0.0103(18) 0.0110(18) 0.0055(18) N5 0.039(2) 0.040(2) 0.045(2) 0.0058(18) 0.0129(18) 0.0102(17) N6 0.037(2) 0.047(2) 0.038(2) -0.0010(19) 0.0082(18) 0.0051(19) N7 0.045(2) 0.053(3) 0.029(2) 0.0098(18) 0.0056(17) 0.0172(19) N8 0.039(2) 0.055(3) 0.037(2) 0.006(2) 0.0083(18) 0.0134(19) N9 0.042(2) 0.044(2) 0.037(2) 0.0074(18) 0.0076(17) -0.0087(18) N10 0.049(2) 0.029(2) 0.041(2) 0.0044(17) 0.0180(19) -0.0097(17) N11 0.042(2) 0.036(2) 0.048(2) -0.0179(18) 0.0139(18) -0.0163(17) N12 0.052(2) 0.034(2) 0.034(2) -0.0111(18) 0.0112(18) -0.0052(18) N13 0.039(2) 0.046(2) 0.038(2) 0.0084(19) 0.0127(18) 0.0142(19) N14 0.046(2) 0.044(2) 0.040(2) 0.0125(19) 0.0146(19) 0.0134(19) N15 0.038(2) 0.047(2) 0.040(2) 0.0076(19) 0.0073(17) 0.0109(18) N16 0.046(2) 0.054(3) 0.032(2) 0.009(2) 0.0086(19) 0.019(2) O1 0.0315(16) 0.0287(16) 0.0339(15) -0.0124(13) 0.0104(12) 0.0057(12) O2 0.047(2) 0.0469(19) 0.0436(18) 0.0106(15) 0.0120(15) 0.0001(15) O3 0.043(2) 0.074(2) 0.051(2) 0.0105(17) 0.0098(16) 0.0110(17) O4 0.0432(19) 0.055(2) 0.050(2) 0.0182(17) 0.0111(15) -0.0019(16) O5 0.045(2) 0.071(2) 0.052(2) 0.0137(17) 0.0137(16) 0.0115(17) O6 0.042(2) 0.070(2) 0.0468(19) 0.0003(18) 0.0141(15) -0.0096(18) O7 0.049(2) 0.0349(18) 0.070(2) -0.0155(16) 0.0247(16) 0.0072(15) O8 0.0386(19) 0.0401(18) 0.063(2) 0.0072(16) 0.0229(15) 0.0077(15) O9 0.058(2) 0.060(2) 0.047(2) -0.0063(17) 0.0162(17) 0.0008(17) O10 0.0417(19) 0.0447(19) 0.0363(17) 0.0079(14) 0.0130(14) -0.0031(14) O11 0.063(2) 0.058(2) 0.054(2) 0.0174(17) 0.0083(17) 0.0044(18) O12 0.0419(18) 0.0310(17) 0.0496(18) 0.0107(14) 0.0202(14) 0.0153(14) O13 0.0367(18) 0.0443(19) 0.0339(16) 0.0092(14) 0.0117(13) -0.0109(14) O14 0.046(2) 0.053(2) 0.055(2) -0.0241(16) 0.0152(17) -0.0125(16) O15 0.042(2) 0.0449(19) 0.0449(18) 0.0073(15) 0.0142(15) 0.0170(15) O16 0.0409(18) 0.0348(18) 0.0459(18) 0.0119(14) 0.0159(14) 0.0137(14) S1 0.0464(7) 0.0539(8) 0.0394(7) 0.0106(6) 0.0117(5) 0.0169(6) S2 0.0480(8) 0.0508(8) 0.0428(7) 0.0101(6) 0.0125(6) 0.0139(6) S3 0.0488(8) 0.0403(7) 0.0405(7) 0.0090(5) 0.0116(6) 0.0123(5) S4 0.0513(8) 0.0406(7) 0.0400(7) 0.0086(5) 0.0136(6) 0.0111(6) S5 0.0537(8) 0.0356(7) 0.0393(7) -0.0096(5) 0.0146(6) 0.0060(5) S6 0.0540(8) 0.0395(7) 0.0413(7) -0.0127(5) 0.0146(6) -0.0159(6) S7 0.0458(7) 0.0531(8) 0.0410(7) 0.0071(6) 0.0113(6) 0.0083(6) S8 0.0504(8) 0.0515(8) 0.0382(7) 0.0083(6) 0.0111(6) -0.0107(6) Zn1 0.0332(3) 0.0326(3) 0.0326(3) -0.0113(2) 0.0108(2) 0.0111(2) Zn2 0.0356(3) 0.0326(3) 0.0333(3) 0.0072(2) 0.0110(2) -0.0071(2) Zn3 0.0319(3) 0.0411(3) 0.0334(3) 0.0069(2) 0.0096(2) 0.0151(2) Zn4 0.0333(3) 0.0415(3) 0.0315(3) 0.0111(2) 0.0094(2) 0.0131(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 C1 N1 1.344(4) . ? C1 C2 1.365(5) . ? C1 H1 0.9300 . ? C2 N2 1.391(5) . ? C2 H2 0.9300 . ? C3 N1 1.324(5) . ? C3 N2 1.328(4) . ? C3 H3 0.9300 . ? C4 C5 1.340(5) . ? C4 N2 1.423(5) . ? C4 S3 1.691(4) . ? C5 C6 1.444(5) . ? C5 H5 0.9300 . ? C6 C7 1.354(5) . ? C6 H6 0.9300 . ? C7 C8 1.452(5) . ? C7 S3 1.709(4) . ? C8 C9 1.366(5) . ? C8 S4 1.726(4) . ? C9 C10 1.429(5) . ? C9 H9 0.9300 . ? C10 C11 1.320(5) . ? C10 H10 0.9300 . ? C11 N3 1.422(5) . ? C11 S4 1.708(4) . ? C12 N3 1.299(4) . ? C12 N4 1.339(5) . ? C12 H12 0.9300 . ? C13 C14 1.360(5) . ? C13 N3 1.362(5) . ? C13 H13 0.9300 . ? C14 N4 1.368(5) . ? C14 H14 0.9300 . ? C15 N5 1.332(5) . ? C15 N6 1.341(4) . ? C15 H15 0.9300 . ? C16 C17 1.345(5) . ? C16 N5 1.350(5) . ? C16 H16 0.9300 . ? C17 N6 1.433(5) . ? C17 H17 0.9300 . ? C18 C19 1.349(5) . ? C18 N6 1.368(5) . ? C18 S1 1.716(4) . ? C19 C20 1.394(5) . ? C19 H19 0.9300 . ? C20 C21 1.365(5) . ? C20 H20 0.9300 . ? C21 C22 1.443(6) . ? C21 S1 1.707(4) . ? C22 C23 1.335(5) . ? C22 S2 1.719(4) . ? C23 C24 1.415(5) . ? C23 H23 0.9300 . ? C24 C25 1.333(5) . ? C24 H24 0.9300 . ? C25 N8 1.389(5) . ? C25 S2 1.718(4) . ? C26 N8 1.301(4) . ? C26 N7 1.331(5) . ? C26 H26 0.9300 . ? C27 C28 1.357(5) . ? C27 N8 1.358(5) . ? C27 H27 0.9300 . ? C28 N7 1.340(5) . ? C28 H28 0.9300 . ? C29 N10 1.333(5) . ? C29 N9 1.334(4) . ? C29 H29 0.9300 . ? C30 N9 1.345(5) . ? C30 C31 1.381(5) . ? C30 H30 0.9300 . ? C31 N10 1.358(5) . ? C31 H31 0.9300 . ? C32 C33 1.370(5) . ? C32 N10 1.384(5) . ? C32 S6 1.685(4) . ? C33 C34 1.426(5) . ? C33 H33 0.9300 . ? C34 C35 1.346(5) . ? C34 H34 0.9300 . ? C35 C56 1.369(6) 1_454 ? C35 S6 1.685(4) . ? C36 N13 1.246(5) . ? C36 N14 1.359(5) . ? C36 H36 0.9300 . ? C37 C38 1.291(5) . ? C37 N13 1.364(5) . ? C37 H37 0.9300 . ? C38 N14 1.411(5) . ? C38 H38 0.9300 . ? C39 N15 1.284(5) . ? C39 N16 1.319(5) . ? C39 H39 0.9300 . ? C40 C41 1.334(5) . ? C40 N15 1.347(5) . ? C40 H40 0.9300 . ? C41 N16 1.382(5) . ? C41 H41 0.9300 . ? C42 C43 1.326(5) . ? C42 N16 1.434(5) . ? C42 S8 1.673(4) . ? C43 C44 1.397(5) . ? C43 H43 0.9300 . ? C44 C45 1.314(5) . ? C44 H44 0.9300 . ? C45 C46 1.501(6) . ? C45 S8 1.708(4) . ? C46 C47 1.330(5) . ? C46 S7 1.687(4) . ? C47 C48 1.375(5) . ? C47 H47 0.9300 . ? C48 C49 1.337(5) . ? C48 H48 0.9300 . ? C49 N14 1.434(5) 1_656 ? C49 S7 1.695(4) . ? C50 N11 1.304(5) . ? C50 N12 1.339(4) . ? C50 H50 0.9300 . ? C51 C52 1.365(5) . ? C51 N11 1.373(5) . ? C51 H51 0.9300 . ? C52 N12 1.399(5) . ? C52 H52 0.9300 . ? C53 C54 1.319(5) . ? C53 N12 1.415(5) . ? C53 S5 1.676(4) . ? C54 C55 1.461(5) . ? C54 H54 0.9300 . ? C55 C56 1.338(5) . ? C55 H55 0.9300 . ? C56 C35 1.369(6) 1_656 ? C56 S5 1.743(4) . ? C57 O6 1.234(5) . ? C57 O5 1.270(5) . ? C57 C58 1.473(6) . ? C58 C59 1.406(6) . ? C58 C63 1.415(5) . ? C59 C60 1.363(6) . ? C59 H59 0.9300 . ? C60 C61 1.310(6) . ? C60 H60 0.9300 . ? C61 C62 1.416(5) . ? C61 H61 0.9300 . ? C62 C63 1.379(5) . ? C62 C64 1.461(6) . ? C63 H63 0.9300 . ? C64 O8 1.238(4) . ? C64 O7 1.242(5) . ? C65 O9 1.176(5) . ? C65 O10 1.300(5) . ? C65 C66 1.508(6) . ? C66 C71 1.376(6) . ? C66 C67 1.398(6) . ? C67 C68 1.359(5) . ? C67 H67 0.9300 . ? C68 C69 1.400(5) . ? C68 H68 0.9300 . ? C69 C70 1.380(5) . ? C69 H69 0.9300 . ? C70 C71 1.382(5) . ? C70 C72 1.501(6) . ? C71 H71 0.9300 . ? C72 O12 1.222(5) . ? C72 O11 1.286(5) . ? C73 O2 1.252(4) . ? C73 O1 1.280(4) . ? C73 C74 1.448(5) . ? C74 C75 1.355(5) . ? C74 C79 1.418(5) . ? C75 C76 1.383(5) . ? C75 H75 0.9300 . ? C76 C77 1.397(6) . ? C76 C80 1.492(6) . ? C77 C78 1.382(6) . ? C77 H77 0.9300 . ? C78 C79 1.359(5) . ? C78 H78 0.9300 . ? C79 H79 0.9300 . ? C80 O4 1.209(5) . ? C80 O3 1.271(5) . ? C81 O14 1.174(5) . ? C81 O13 1.243(5) . ? C81 C82 1.511(6) . ? C81 Zn2 2.596(5) . ? C82 C87 1.374(6) . ? C82 C83 1.417(5) . ? C83 C84 1.344(5) . ? C83 H83 0.9300 . ? C84 C85 1.426(6) . ? C84 H84 0.9300 . ? C85 C86 1.387(6) . ? C85 H85 0.9300 . ? C86 C87 1.353(6) . ? C86 C88 1.503(6) . ? C87 H87 0.9300 . ? C88 O15 1.155(5) . ? C88 O16 1.263(5) . ? N1 Zn1 2.033(3) . ? N4 Zn2 2.002(3) . ? N5 Zn3 2.023(3) . ? N7 Zn4 2.038(3) . ? N9 Zn2 2.037(3) . ? N11 Zn1 2.032(3) . ? N13 Zn3 2.013(3) . ? N14 C49 1.434(5) 1_454 ? N15 Zn4 2.033(3) . ? O1 Zn1 2.089(2) . ? O4 Zn4 1.964(3) 1_655 ? O6 Zn1 2.139(3) . ? O8 Zn4 2.119(3) . ? O10 Zn2 2.201(3) . ? O12 Zn3 2.122(3) . ? O13 Zn2 2.047(2) . ? O15 Zn3 2.324(3) 1_655 ? O16 Zn3 2.337(3) 1_655 ? Zn3 O15 2.324(3) 1_455 ? Zn3 O16 2.337(3) 1_455 ? Zn4 O4 1.964(3) 1_455 ? 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 N1 C1 C2 110.3(4) . . ? N1 C1 H1 124.8 . . ? C2 C1 H1 124.8 . . ? C1 C2 N2 105.3(3) . . ? C1 C2 H2 127.4 . . ? N2 C2 H2 127.4 . . ? N1 C3 N2 112.1(4) . . ? N1 C3 H3 124.0 . . ? N2 C3 H3 124.0 . . ? C5 C4 N2 125.9(4) . . ? C5 C4 S3 115.2(3) . . ? N2 C4 S3 118.8(3) . . ? C4 C5 C6 108.8(4) . . ? C4 C5 H5 125.6 . . ? C6 C5 H5 125.6 . . ? C7 C6 C5 113.9(4) . . ? C7 C6 H6 123.0 . . ? C5 C6 H6 123.0 . . ? C6 C7 C8 129.3(4) . . ? C6 C7 S3 111.0(3) . . ? C8 C7 S3 119.7(3) . . ? C9 C8 C7 130.9(4) . . ? C9 C8 S4 108.8(3) . . ? C7 C8 S4 120.3(3) . . ? C8 C9 C10 114.7(4) . . ? C8 C9 H9 122.7 . . ? C10 C9 H9 122.7 . . ? C11 C10 C9 110.8(4) . . ? C11 C10 H10 124.6 . . ? C9 C10 H10 124.6 . . ? C10 C11 N3 126.9(4) . . ? C10 C11 S4 113.6(3) . . ? N3 C11 S4 119.4(3) . . ? N3 C12 N4 113.0(4) . . ? N3 C12 H12 123.5 . . ? N4 C12 H12 123.5 . . ? C14 C13 N3 106.6(4) . . ? C14 C13 H13 126.7 . . ? N3 C13 H13 126.7 . . ? C13 C14 N4 109.1(4) . . ? C13 C14 H14 125.4 . . ? N4 C14 H14 125.4 . . ? N5 C15 N6 113.4(4) . . ? N5 C15 H15 123.3 . . ? N6 C15 H15 123.3 . . ? C17 C16 N5 114.2(4) . . ? C17 C16 H16 122.9 . . ? N5 C16 H16 122.9 . . ? C16 C17 N6 103.3(4) . . ? C16 C17 H17 128.3 . . ? N6 C17 H17 128.3 . . ? C19 C18 N6 128.7(4) . . ? C19 C18 S1 110.8(3) . . ? N6 C18 S1 120.5(3) . . ? C18 C19 C20 113.0(4) . . ? C18 C19 H19 123.5 . . ? C20 C19 H19 123.5 . . ? C21 C20 C19 113.4(4) . . ? C21 C20 H20 123.3 . . ? C19 C20 H20 123.3 . . ? C20 C21 C22 130.2(4) . . ? C20 C21 S1 110.3(3) . . ? C22 C21 S1 119.4(3) . . ? C23 C22 C21 130.6(4) . . ? C23 C22 S2 108.8(3) . . ? C21 C22 S2 120.6(3) . . ? C22 C23 C24 115.6(4) . . ? C22 C23 H23 122.2 . . ? C24 C23 H23 122.2 . . ? C25 C24 C23 111.7(4) . . ? C25 C24 H24 124.1 . . ? C23 C24 H24 124.1 . . ? C24 C25 N8 128.6(4) . . ? C24 C25 S2 111.1(3) . . ? N8 C25 S2 120.3(3) . . ? N8 C26 N7 111.1(4) . . ? N8 C26 H26 124.4 . . ? N7 C26 H26 124.4 . . ? C28 C27 N8 105.9(4) . . ? C28 C27 H27 127.0 . . ? N8 C27 H27 127.0 . . ? N7 C28 C27 109.2(4) . . ? N7 C28 H28 125.4 . . ? C27 C28 H28 125.4 . . ? N10 C29 N9 111.6(3) . . ? N10 C29 H29 124.2 . . ? N9 C29 H29 124.2 . . ? N9 C30 C31 109.6(4) . . ? N9 C30 H30 125.2 . . ? C31 C30 H30 125.2 . . ? N10 C31 C30 105.9(4) . . ? N10 C31 H31 127.0 . . ? C30 C31 H31 127.0 . . ? C33 C32 N10 127.3(4) . . ? C33 C32 S6 109.7(3) . . ? N10 C32 S6 122.9(3) . . ? C32 C33 C34 109.7(4) . . ? C32 C33 H33 125.1 . . ? C34 C33 H33 125.1 . . ? C35 C34 C33 117.1(4) . . ? C35 C34 H34 121.4 . . ? C33 C34 H34 121.4 . . ? C34 C35 C56 127.8(4) . 1_454 ? C34 C35 S6 106.2(3) . . ? C56 C35 S6 125.2(4) 1_454 . ? N13 C36 N14 115.7(4) . . ? N13 C36 H36 122.1 . . ? N14 C36 H36 122.1 . . ? C38 C37 N13 113.0(4) . . ? C38 C37 H37 123.5 . . ? N13 C37 H37 123.5 . . ? C37 C38 N14 105.7(4) . . ? C37 C38 H38 127.2 . . ? N14 C38 H38 127.2 . . ? N15 C39 N16 113.5(4) . . ? N15 C39 H39 123.2 . . ? N16 C39 H39 123.2 . . ? C41 C40 N15 109.5(4) . . ? C41 C40 H40 125.3 . . ? N15 C40 H40 125.3 . . ? C40 C41 N16 106.5(4) . . ? C40 C41 H41 126.8 . . ? N16 C41 H41 126.8 . . ? C43 C42 N16 125.3(4) . . ? C43 C42 S8 115.0(4) . . ? N16 C42 S8 119.6(3) . . ? C42 C43 C44 108.2(4) . . ? C42 C43 H43 125.9 . . ? C44 C43 H43 125.9 . . ? C45 C44 C43 116.5(4) . . ? C45 C44 H44 121.7 . . ? C43 C44 H44 121.7 . . ? C44 C45 C46 130.8(4) . . ? C44 C45 S8 109.5(3) . . ? C46 C45 S8 119.7(3) . . ? C47 C46 C45 129.4(4) . . ? C47 C46 S7 111.7(4) . . ? C45 C46 S7 118.8(3) . . ? C46 C47 C48 113.2(4) . . ? C46 C47 H47 123.4 . . ? C48 C47 H47 123.4 . . ? C49 C48 C47 111.7(4) . . ? C49 C48 H48 124.1 . . ? C47 C48 H48 124.1 . . ? C48 C49 N14 128.3(4) . 1_656 ? C48 C49 S7 112.1(4) . . ? N14 C49 S7 119.6(3) 1_656 . ? N11 C50 N12 114.1(4) . . ? N11 C50 H50 122.9 . . ? N12 C50 H50 122.9 . . ? C52 C51 N11 109.4(4) . . ? C52 C51 H51 125.3 . . ? N11 C51 H51 125.3 . . ? C51 C52 N12 106.4(4) . . ? C51 C52 H52 126.8 . . ? N12 C52 H52 126.8 . . ? C54 C53 N12 126.2(4) . . ? C54 C53 S5 115.0(3) . . ? N12 C53 S5 118.8(3) . . ? C53 C54 C55 109.6(4) . . ? C53 C54 H54 125.2 . . ? C55 C54 H54 125.2 . . ? C56 C55 C54 114.5(4) . . ? C56 C55 H55 122.7 . . ? C54 C55 H55 122.7 . . ? C55 C56 C35 128.4(4) . 1_656 ? C55 C56 S5 109.0(3) . . ? C35 C56 S5 122.6(3) 1_656 . ? O6 C57 O5 121.1(5) . . ? O6 C57 C58 116.7(5) . . ? O5 C57 C58 122.2(5) . . ? C59 C58 C63 117.9(4) . . ? C59 C58 C57 119.9(4) . . ? C63 C58 C57 121.8(5) . . ? C60 C59 C58 119.8(4) . . ? C60 C59 H59 120.1 . . ? C58 C59 H59 120.1 . . ? C61 C60 C59 122.0(4) . . ? C61 C60 H60 119.0 . . ? C59 C60 H60 119.0 . . ? C60 C61 C62 121.9(4) . . ? C60 C61 H61 119.1 . . ? C62 C61 H61 119.1 . . ? C63 C62 C61 117.5(4) . . ? C63 C62 C64 121.2(4) . . ? C61 C62 C64 121.1(4) . . ? C62 C63 C58 120.9(4) . . ? C62 C63 H63 119.6 . . ? C58 C63 H63 119.6 . . ? O8 C64 O7 126.6(4) . . ? O8 C64 C62 115.6(4) . . ? O7 C64 C62 117.7(4) . . ? O9 C65 O10 126.2(4) . . ? O9 C65 C66 119.6(5) . . ? O10 C65 C66 113.9(4) . . ? C71 C66 C67 118.8(4) . . ? C71 C66 C65 119.8(5) . . ? C67 C66 C65 120.6(5) . . ? C68 C67 C66 121.2(5) . . ? C68 C67 H67 119.4 . . ? C66 C67 H67 119.4 . . ? C67 C68 C69 119.8(4) . . ? C67 C68 H68 120.1 . . ? C69 C68 H68 120.1 . . ? C70 C69 C68 119.2(4) . . ? C70 C69 H69 120.4 . . ? C68 C69 H69 120.4 . . ? C69 C70 C71 120.6(4) . . ? C69 C70 C72 118.8(4) . . ? C71 C70 C72 120.4(4) . . ? C66 C71 C70 120.3(5) . . ? C66 C71 H71 119.9 . . ? C70 C71 H71 119.9 . . ? O12 C72 O11 128.6(5) . . ? O12 C72 C70 113.5(4) . . ? O11 C72 C70 117.8(4) . . ? O2 C73 O1 119.2(4) . . ? O2 C73 C74 124.7(4) . . ? O1 C73 C74 115.8(4) . . ? C75 C74 C79 120.8(4) . . ? C75 C74 C73 122.8(4) . . ? C79 C74 C73 116.1(4) . . ? C74 C75 C76 119.7(4) . . ? C74 C75 H75 120.2 . . ? C76 C75 H75 120.2 . . ? C75 C76 C77 119.9(4) . . ? C75 C76 C80 119.5(4) . . ? C77 C76 C80 120.5(4) . . ? C78 C77 C76 119.9(4) . . ? C78 C77 H77 120.0 . . ? C76 C77 H77 120.0 . . ? C79 C78 C77 120.4(5) . . ? C79 C78 H78 119.8 . . ? C77 C78 H78 119.8 . . ? C78 C79 C74 119.3(4) . . ? C78 C79 H79 120.3 . . ? C74 C79 H79 120.3 . . ? O4 C80 O3 127.1(5) . . ? O4 C80 C76 115.1(4) . . ? O3 C80 C76 117.7(4) . . ? O14 C81 O13 125.9(5) . . ? O14 C81 C82 118.8(4) . . ? O13 C81 C82 115.1(4) . . ? O14 C81 Zn2 75.8(3) . . ? O13 C81 Zn2 50.7(2) . . ? C82 C81 Zn2 162.0(3) . . ? C87 C82 C83 114.8(4) . . ? C87 C82 C81 119.6(4) . . ? C83 C82 C81 125.6(4) . . ? C84 C83 C82 121.3(4) . . ? C84 C83 H83 119.4 . . ? C82 C83 H83 119.4 . . ? C83 C84 C85 121.3(4) . . ? C83 C84 H84 119.4 . . ? C85 C84 H84 119.4 . . ? C86 C85 C84 118.2(4) . . ? C86 C85 H85 120.9 . . ? C84 C85 H85 120.9 . . ? C87 C86 C85 117.8(4) . . ? C87 C86 C88 121.1(5) . . ? C85 C86 C88 120.7(5) . . ? C86 C87 C82 126.5(4) . . ? C86 C87 H87 116.8 . . ? C82 C87 H87 116.8 . . ? O15 C88 O16 123.1(5) . . ? O15 C88 C86 119.0(4) . . ? O16 C88 C86 117.9(4) . . ? C3 N1 C1 105.8(3) . . ? C3 N1 Zn1 130.7(3) . . ? C1 N1 Zn1 123.2(3) . . ? C3 N2 C2 106.5(4) . . ? C3 N2 C4 127.7(4) . . ? C2 N2 C4 125.8(4) . . ? C12 N3 C13 107.0(4) . . ? C12 N3 C11 127.2(4) . . ? C13 N3 C11 125.8(4) . . ? C12 N4 C14 104.0(3) . . ? C12 N4 Zn2 131.2(3) . . ? C14 N4 Zn2 124.8(3) . . ? C15 N5 C16 103.4(3) . . ? C15 N5 Zn3 131.8(3) . . ? C16 N5 Zn3 124.5(3) . . ? C15 N6 C18 128.5(4) . . ? C15 N6 C17 105.6(4) . . ? C18 N6 C17 125.9(4) . . ? C26 N7 C28 105.9(3) . . ? C26 N7 Zn4 129.0(3) . . ? C28 N7 Zn4 125.1(3) . . ? C26 N8 C27 107.9(4) . . ? C26 N8 C25 127.8(4) . . ? C27 N8 C25 124.3(4) . . ? C29 N9 C30 105.5(3) . . ? C29 N9 Zn2 129.3(3) . . ? C30 N9 Zn2 124.8(3) . . ? C29 N10 C31 107.2(3) . . ? C29 N10 C32 126.2(3) . . ? C31 N10 C32 126.6(4) . . ? C50 N11 C51 105.3(3) . . ? C50 N11 Zn1 132.1(3) . . ? C51 N11 Zn1 122.4(3) . . ? C50 N12 C52 104.8(3) . . ? C50 N12 C53 128.9(4) . . ? C52 N12 C53 126.3(3) . . ? C36 N13 C37 103.4(4) . . ? C36 N13 Zn3 129.8(3) . . ? C37 N13 Zn3 126.2(3) . . ? C36 N14 C38 102.1(4) . . ? C36 N14 C49 131.4(4) . 1_454 ? C38 N14 C49 126.2(4) . 1_454 ? C39 N15 C40 105.7(4) . . ? C39 N15 Zn4 128.9(3) . . ? C40 N15 Zn4 125.2(3) . . ? C39 N16 C41 104.7(4) . . ? C39 N16 C42 128.4(4) . . ? C41 N16 C42 126.7(4) . . ? C73 O1 Zn1 107.1(2) . . ? C80 O4 Zn4 136.2(3) . 1_655 ? C57 O6 Zn1 129.3(3) . . ? C64 O8 Zn4 104.7(3) . . ? C65 O10 Zn2 101.6(3) . . ? C72 O12 Zn3 119.7(3) . . ? C81 O13 Zn2 101.3(3) . . ? C88 O15 Zn3 91.1(3) . 1_655 ? C88 O16 Zn3 87.9(3) . 1_655 ? C21 S1 C18 92.2(2) . . ? C25 S2 C22 92.7(2) . . ? C4 S3 C7 91.0(2) . . ? C11 S4 C8 92.0(2) . . ? C53 S5 C56 91.9(2) . . ? C35 S6 C32 96.3(2) . . ? C46 S7 C49 90.5(2) . . ? C42 S8 C45 90.6(2) . . ? N11 Zn1 N1 114.43(14) . . ? N11 Zn1 O1 98.01(11) . . ? N1 Zn1 O1 102.27(11) . . ? N11 Zn1 O6 90.65(12) . . ? N1 Zn1 O6 125.48(12) . . ? O1 Zn1 O6 122.11(11) . . ? N4 Zn2 N9 114.00(14) . . ? N4 Zn2 O13 97.76(12) . . ? N9 Zn2 O13 91.65(12) . . ? N4 Zn2 O10 96.36(12) . . ? N9 Zn2 O10 94.23(12) . . ? O13 Zn2 O10 160.95(11) . . ? N4 Zn2 C81 114.76(14) . . ? N9 Zn2 C81 103.10(13) . . ? O13 Zn2 C81 28.00(12) . . ? O10 Zn2 C81 133.05(13) . . ? N13 Zn3 N5 113.31(15) . . ? N13 Zn3 O12 90.54(12) . . ? N5 Zn3 O12 122.42(12) . . ? N13 Zn3 O15 136.63(12) . 1_455 ? N5 Zn3 O15 88.08(11) . 1_455 ? O12 Zn3 O15 109.80(10) . 1_455 ? N13 Zn3 O16 84.36(11) . 1_455 ? N5 Zn3 O16 98.85(11) . 1_455 ? O12 Zn3 O16 136.55(9) . 1_455 ? O15 Zn3 O16 54.29(10) 1_455 1_455 ? O4 Zn4 N15 102.94(13) 1_455 . ? O4 Zn4 N7 111.88(12) 1_455 . ? N15 Zn4 N7 113.05(14) . . ? O4 Zn4 O8 109.16(12) 1_455 . ? N15 Zn4 O8 127.97(12) . . ? N7 Zn4 O8 91.62(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 N1 C1 C2 N2 -0.3(5) . . . . ? N2 C4 C5 C6 178.7(4) . . . . ? S3 C4 C5 C6 1.8(5) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C5 C6 C7 C8 179.4(5) . . . . ? C5 C6 C7 S3 -1.8(5) . . . . ? C6 C7 C8 C9 -175.5(4) . . . . ? S3 C7 C8 C9 5.8(8) . . . . ? C6 C7 C8 S4 5.3(7) . . . . ? S3 C7 C8 S4 -173.3(2) . . . . ? C7 C8 C9 C10 177.6(5) . . . . ? S4 C8 C9 C10 -3.2(5) . . . . ? C8 C9 C10 C11 4.7(6) . . . . ? C9 C10 C11 N3 179.6(4) . . . . ? C9 C10 C11 S4 -3.9(5) . . . . ? N3 C13 C14 N4 -1.9(5) . . . . ? N5 C16 C17 N6 1.9(5) . . . . ? N6 C18 C19 C20 -175.8(4) . . . . ? S1 C18 C19 C20 5.7(5) . . . . ? C18 C19 C20 C21 -5.6(6) . . . . ? C19 C20 C21 C22 -174.7(4) . . . . ? C19 C20 C21 S1 2.9(5) . . . . ? C20 C21 C22 C23 -174.2(5) . . . . ? S1 C21 C22 C23 8.5(7) . . . . ? C20 C21 C22 S2 5.1(7) . . . . ? S1 C21 C22 S2 -172.2(2) . . . . ? C21 C22 C23 C24 175.7(5) . . . . ? S2 C22 C23 C24 -3.6(5) . . . . ? C22 C23 C24 C25 3.9(6) . . . . ? C23 C24 C25 N8 179.3(4) . . . . ? C23 C24 C25 S2 -2.2(5) . . . . ? N8 C27 C28 N7 -0.7(5) . . . . ? N9 C30 C31 N10 -1.2(5) . . . . ? N10 C32 C33 C34 -175.5(4) . . . . ? S6 C32 C33 C34 1.5(5) . . . . ? C32 C33 C34 C35 -8.2(6) . . . . ? C33 C34 C35 C56 -179.3(5) . . . 1_454 ? C33 C34 C35 S6 10.5(5) . . . . ? N13 C37 C38 N14 -1.6(5) . . . . ? N15 C40 C41 N16 3.3(5) . . . . ? N16 C42 C43 C44 174.4(4) . . . . ? S8 C42 C43 C44 -2.1(5) . . . . ? C42 C43 C44 C45 4.1(6) . . . . ? C43 C44 C45 C46 177.0(4) . . . . ? C43 C44 C45 S8 -4.1(5) . . . . ? C44 C45 C46 C47 174.2(4) . . . . ? S8 C45 C46 C47 -4.6(6) . . . . ? C44 C45 C46 S7 -7.3(7) . . . . ? S8 C45 C46 S7 173.9(2) . . . . ? C45 C46 C47 C48 -173.4(4) . . . . ? S7 C46 C47 C48 8.0(5) . . . . ? C46 C47 C48 C49 -9.0(6) . . . . ? C47 C48 C49 N14 -171.7(4) . . . 1_656 ? C47 C48 C49 S7 5.8(5) . . . . ? N11 C51 C52 N12 -1.8(5) . . . . ? N12 C53 C54 C55 179.5(4) . . . . ? S5 C53 C54 C55 0.6(5) . . . . ? C53 C54 C55 C56 -1.0(6) . . . . ? C54 C55 C56 C35 -178.5(5) . . . 1_656 ? C54 C55 C56 S5 1.0(5) . . . . ? O6 C57 C58 C59 176.9(4) . . . . ? O5 C57 C58 C59 -2.6(6) . . . . ? O6 C57 C58 C63 4.7(6) . . . . ? O5 C57 C58 C63 -174.9(4) . . . . ? C63 C58 C59 C60 -0.7(6) . . . . ? C57 C58 C59 C60 -173.2(4) . . . . ? C58 C59 C60 C61 0.1(7) . . . . ? C59 C60 C61 C62 0.2(7) . . . . ? C60 C61 C62 C63 0.1(6) . . . . ? C60 C61 C62 C64 -176.2(4) . . . . ? C61 C62 C63 C58 -0.7(6) . . . . ? C64 C62 C63 C58 175.6(4) . . . . ? C59 C58 C63 C62 1.0(6) . . . . ? C57 C58 C63 C62 173.4(4) . . . . ? C63 C62 C64 O8 168.5(4) . . . . ? C61 C62 C64 O8 -15.3(6) . . . . ? C63 C62 C64 O7 -15.3(6) . . . . ? C61 C62 C64 O7 160.9(4) . . . . ? O9 C65 C66 C71 -146.1(5) . . . . ? O10 C65 C66 C71 27.8(6) . . . . ? O9 C65 C66 C67 44.1(6) . . . . ? O10 C65 C66 C67 -142.0(4) . . . . ? C71 C66 C67 C68 3.3(6) . . . . ? C65 C66 C67 C68 173.2(4) . . . . ? C66 C67 C68 C69 -1.8(6) . . . . ? C67 C68 C69 C70 0.0(6) . . . . ? C68 C69 C70 C71 0.4(6) . . . . ? C68 C69 C70 C72 176.2(4) . . . . ? C67 C66 C71 C70 -2.9(6) . . . . ? C65 C66 C71 C70 -172.9(4) . . . . ? C69 C70 C71 C66 1.2(6) . . . . ? C72 C70 C71 C66 -174.6(4) . . . . ? C69 C70 C72 O12 -175.2(4) . . . . ? C71 C70 C72 O12 0.7(6) . . . . ? C69 C70 C72 O11 2.0(6) . . . . ? C71 C70 C72 O11 177.9(4) . . . . ? O2 C73 C74 C75 147.8(4) . . . . ? O1 C73 C74 C75 -25.5(6) . . . . ? O2 C73 C74 C79 -39.0(6) . . . . ? O1 C73 C74 C79 147.8(4) . . . . ? C79 C74 C75 C76 0.6(6) . . . . ? C73 C74 C75 C76 173.6(4) . . . . ? C74 C75 C76 C77 -0.9(6) . . . . ? C74 C75 C76 C80 176.0(4) . . . . ? C75 C76 C77 C78 0.3(7) . . . . ? C80 C76 C77 C78 -176.6(4) . . . . ? C76 C77 C78 C79 0.6(7) . . . . ? C77 C78 C79 C74 -0.8(6) . . . . ? C75 C74 C79 C78 0.2(6) . . . . ? C73 C74 C79 C78 -173.2(4) . . . . ? C75 C76 C80 O4 -32.0(6) . . . . ? C77 C76 C80 O4 144.9(4) . . . . ? C75 C76 C80 O3 144.1(4) . . . . ? C77 C76 C80 O3 -39.0(6) . . . . ? O14 C81 C82 C87 -178.2(4) . . . . ? O13 C81 C82 C87 5.3(6) . . . . ? Zn2 C81 C82 C87 39.8(12) . . . . ? O14 C81 C82 C83 3.7(7) . . . . ? O13 C81 C82 C83 -172.8(4) . . . . ? Zn2 C81 C82 C83 -138.3(9) . . . . ? C87 C82 C83 C84 -5.0(6) . . . . ? C81 C82 C83 C84 173.2(4) . . . . ? C82 C83 C84 C85 2.6(6) . . . . ? C83 C84 C85 C86 0.5(6) . . . . ? C84 C85 C86 C87 -0.9(6) . . . . ? C84 C85 C86 C88 172.6(4) . . . . ? C85 C86 C87 C82 -2.0(7) . . . . ? C88 C86 C87 C82 -175.5(4) . . . . ? C83 C82 C87 C86 4.9(6) . . . . ? C81 C82 C87 C86 -173.5(4) . . . . ? C87 C86 C88 O15 -148.5(5) . . . . ? C85 C86 C88 O15 38.2(6) . . . . ? C87 C86 C88 O16 29.3(6) . . . . ? C85 C86 C88 O16 -144.0(4) . . . . ? N2 C3 N1 C1 2.3(5) . . . . ? N2 C3 N1 Zn1 -172.0(3) . . . . ? C2 C1 N1 C3 -1.1(5) . . . . ? C2 C1 N1 Zn1 173.6(3) . . . . ? N1 C3 N2 C2 -2.5(5) . . . . ? N1 C3 N2 C4 175.6(4) . . . . ? C1 C2 N2 C3 1.6(5) . . . . ? C1 C2 N2 C4 -176.5(4) . . . . ? C5 C4 N2 C3 162.6(4) . . . . ? S3 C4 N2 C3 -20.5(6) . . . . ? C5 C4 N2 C2 -19.6(7) . . . . ? S3 C4 N2 C2 157.2(3) . . . . ? N4 C12 N3 C13 3.4(5) . . . . ? N4 C12 N3 C11 -176.1(4) . . . . ? C14 C13 N3 C12 -0.8(5) . . . . ? C14 C13 N3 C11 178.7(4) . . . . ? C10 C11 N3 C12 179.5(5) . . . . ? S4 C11 N3 C12 3.2(6) . . . . ? C10 C11 N3 C13 0.1(7) . . . . ? S4 C11 N3 C13 -176.2(3) . . . . ? N3 C12 N4 C14 -4.4(5) . . . . ? N3 C12 N4 Zn2 175.1(3) . . . . ? C13 C14 N4 C12 3.7(5) . . . . ? C13 C14 N4 Zn2 -175.8(3) . . . . ? N6 C15 N5 C16 -1.3(5) . . . . ? N6 C15 N5 Zn3 173.5(3) . . . . ? C17 C16 N5 C15 -0.5(5) . . . . ? C17 C16 N5 Zn3 -175.8(3) . . . . ? N5 C15 N6 C18 -177.4(4) . . . . ? N5 C15 N6 C17 2.4(5) . . . . ? C19 C18 N6 C15 -163.5(4) . . . . ? S1 C18 N6 C15 14.9(6) . . . . ? C19 C18 N6 C17 16.7(7) . . . . ? S1 C18 N6 C17 -164.9(3) . . . . ? C16 C17 N6 C15 -2.5(5) . . . . ? C16 C17 N6 C18 177.3(4) . . . . ? N8 C26 N7 C28 -0.2(5) . . . . ? N8 C26 N7 Zn4 -179.9(3) . . . . ? C27 C28 N7 C26 0.6(5) . . . . ? C27 C28 N7 Zn4 -179.8(3) . . . . ? N7 C26 N8 C27 -0.2(5) . . . . ? N7 C26 N8 C25 176.5(4) . . . . ? C28 C27 N8 C26 0.5(5) . . . . ? C28 C27 N8 C25 -176.3(4) . . . . ? C24 C25 N8 C26 164.8(5) . . . . ? S2 C25 N8 C26 -13.6(6) . . . . ? C24 C25 N8 C27 -19.0(7) . . . . ? S2 C25 N8 C27 162.6(3) . . . . ? N10 C29 N9 C30 -5.7(5) . . . . ? N10 C29 N9 Zn2 -178.6(3) . . . . ? C31 C30 N9 C29 4.1(5) . . . . ? C31 C30 N9 Zn2 177.4(3) . . . . ? N9 C29 N10 C31 5.1(5) . . . . ? N9 C29 N10 C32 -176.4(4) . . . . ? C30 C31 N10 C29 -2.3(5) . . . . ? C30 C31 N10 C32 179.2(4) . . . . ? C33 C32 N10 C29 170.7(4) . . . . ? S6 C32 N10 C29 -5.9(6) . . . . ? C33 C32 N10 C31 -11.1(7) . . . . ? S6 C32 N10 C31 172.3(3) . . . . ? N12 C50 N11 C51 0.7(5) . . . . ? N12 C50 N11 Zn1 -173.7(3) . . . . ? C52 C51 N11 C50 0.7(5) . . . . ? C52 C51 N11 Zn1 175.8(3) . . . . ? N11 C50 N12 C52 -1.7(5) . . . . ? N11 C50 N12 C53 177.3(4) . . . . ? C51 C52 N12 C50 2.1(5) . . . . ? C51 C52 N12 C53 -177.1(4) . . . . ? C54 C53 N12 C50 -172.9(4) . . . . ? S5 C53 N12 C50 5.9(6) . . . . ? C54 C53 N12 C52 6.0(7) . . . . ? S5 C53 N12 C52 -175.2(3) . . . . ? N14 C36 N13 C37 2.9(5) . . . . ? N14 C36 N13 Zn3 174.0(2) . . . . ? C38 C37 N13 C36 -0.7(5) . . . . ? C38 C37 N13 Zn3 -172.2(3) . . . . ? N13 C36 N14 C38 -3.8(5) . . . . ? N13 C36 N14 C49 -178.1(4) . . . 1_454 ? C37 C38 N14 C36 3.0(5) . . . . ? C37 C38 N14 C49 177.7(4) . . . 1_454 ? N16 C39 N15 C40 -1.9(5) . . . . ? N16 C39 N15 Zn4 -176.9(2) . . . . ? C41 C40 N15 C39 -1.0(5) . . . . ? C41 C40 N15 Zn4 174.3(3) . . . . ? N15 C39 N16 C41 3.9(5) . . . . ? N15 C39 N16 C42 178.3(4) . . . . ? C40 C41 N16 C39 -4.3(5) . . . . ? C40 C41 N16 C42 -178.8(4) . . . . ? C43 C42 N16 C39 -171.1(4) . . . . ? S8 C42 N16 C39 5.3(6) . . . . ? C43 C42 N16 C41 2.2(7) . . . . ? S8 C42 N16 C41 178.6(3) . . . . ? O2 C73 O1 Zn1 30.1(5) . . . . ? C74 C73 O1 Zn1 -156.3(3) . . . . ? O3 C80 O4 Zn4 20.6(8) . . . 1_655 ? C76 C80 O4 Zn4 -163.8(3) . . . 1_655 ? O5 C57 O6 Zn1 43.6(6) . . . . ? C58 C57 O6 Zn1 -135.9(3) . . . . ? O7 C64 O8 Zn4 -16.4(5) . . . . ? C62 C64 O8 Zn4 159.4(3) . . . . ? O9 C65 O10 Zn2 -35.8(6) . . . . ? C66 C65 O10 Zn2 150.8(3) . . . . ? O11 C72 O12 Zn3 -37.0(6) . . . . ? C70 C72 O12 Zn3 139.8(3) . . . . ? O14 C81 O13 Zn2 -9.2(5) . . . . ? C82 C81 O13 Zn2 167.0(3) . . . . ? O16 C88 O15 Zn3 19.6(5) . . . 1_655 ? C86 C88 O15 Zn3 -162.8(4) . . . 1_655 ? O15 C88 O16 Zn3 -19.5(5) . . . 1_655 ? C86 C88 O16 Zn3 162.8(4) . . . 1_655 ? C20 C21 S1 C18 0.3(4) . . . . ? C22 C21 S1 C18 178.1(4) . . . . ? C19 C18 S1 C21 -3.5(3) . . . . ? N6 C18 S1 C21 177.9(4) . . . . ? C24 C25 S2 C22 0.2(4) . . . . ? N8 C25 S2 C22 178.8(4) . . . . ? C23 C22 S2 C25 2.0(4) . . . . ? C21 C22 S2 C25 -177.5(4) . . . . ? C5 C4 S3 C7 -2.4(4) . . . . ? N2 C4 S3 C7 -179.6(4) . . . . ? C6 C7 S3 C4 2.4(4) . . . . ? C8 C7 S3 C4 -178.8(4) . . . . ? C10 C11 S4 C8 1.8(4) . . . . ? N3 C11 S4 C8 178.6(4) . . . . ? C9 C8 S4 C11 0.9(4) . . . . ? C7 C8 S4 C11 -179.8(4) . . . . ? C54 C53 S5 C56 -0.1(4) . . . . ? N12 C53 S5 C56 -179.0(3) . . . . ? C55 C56 S5 C53 -0.5(3) . . . . ? C35 C56 S5 C53 179.0(4) 1_656 . . . ? C34 C35 S6 C32 -8.0(4) . . . . ? C56 C35 S6 C32 -178.5(4) 1_454 . . . ? C33 C32 S6 C35 3.8(4) . . . . ? N10 C32 S6 C35 -179.1(4) . . . . ? C47 C46 S7 C49 -3.9(3) . . . . ? C45 C46 S7 C49 177.3(3) . . . . ? C48 C49 S7 C46 -1.2(3) . . . . ? N14 C49 S7 C46 176.6(3) 1_656 . . . ? C43 C42 S8 C45 0.0(4) . . . . ? N16 C42 S8 C45 -176.8(3) . . . . ? C44 C45 S8 C42 2.3(3) . . . . ? C46 C45 S8 C42 -178.6(3) . . . . ? C50 N11 Zn1 N1 -44.8(4) . . . . ? C51 N11 Zn1 N1 141.7(3) . . . . ? C50 N11 Zn1 O1 62.7(4) . . . . ? C51 N11 Zn1 O1 -110.9(3) . . . . ? C50 N11 Zn1 O6 -174.7(4) . . . . ? C51 N11 Zn1 O6 11.7(3) . . . . ? C3 N1 Zn1 N11 -24.3(4) . . . . ? C1 N1 Zn1 N11 162.3(3) . . . . ? C3 N1 Zn1 O1 -129.1(4) . . . . ? C1 N1 Zn1 O1 57.5(3) . . . . ? C3 N1 Zn1 O6 85.5(4) . . . . ? C1 N1 Zn1 O6 -87.9(3) . . . . ? C73 O1 Zn1 N11 154.5(3) . . . . ? C73 O1 Zn1 N1 -88.2(3) . . . . ? C73 O1 Zn1 O6 58.7(3) . . . . ? C57 O6 Zn1 N11 -147.6(4) . . . . ? C57 O6 Zn1 N1 91.4(4) . . . . ? C57 O6 Zn1 O1 -47.7(4) . . . . ? C12 N4 Zn2 N9 33.5(4) . . . . ? C14 N4 Zn2 N9 -147.1(3) . . . . ? C12 N4 Zn2 O13 -61.8(4) . . . . ? C14 N4 Zn2 O13 117.6(3) . . . . ? C12 N4 Zn2 O10 131.0(4) . . . . ? C14 N4 Zn2 O10 -49.6(3) . . . . ? C12 N4 Zn2 C81 -85.1(4) . . . . ? C14 N4 Zn2 C81 94.3(3) . . . . ? C29 N9 Zn2 N4 40.1(4) . . . . ? C30 N9 Zn2 N4 -131.5(3) . . . . ? C29 N9 Zn2 O13 139.4(4) . . . . ? C30 N9 Zn2 O13 -32.3(3) . . . . ? C29 N9 Zn2 O10 -58.8(4) . . . . ? C30 N9 Zn2 O10 129.6(3) . . . . ? C29 N9 Zn2 C81 165.2(4) . . . . ? C30 N9 Zn2 C81 -6.5(4) . . . . ? C81 O13 Zn2 N4 -130.1(3) . . . . ? C81 O13 Zn2 N9 115.4(3) . . . . ? C81 O13 Zn2 O10 7.4(5) . . . . ? C65 O10 Zn2 N4 90.5(3) . . . . ? C65 O10 Zn2 N9 -154.7(3) . . . . ? C65 O10 Zn2 O13 -47.1(4) . . . . ? C65 O10 Zn2 C81 -42.4(3) . . . . ? O14 C81 Zn2 N4 -131.1(3) . . . . ? O13 C81 Zn2 N4 56.6(3) . . . . ? C82 C81 Zn2 N4 15.0(11) . . . . ? O14 C81 Zn2 N9 104.3(3) . . . . ? O13 C81 Zn2 N9 -68.0(3) . . . . ? C82 C81 Zn2 N9 -109.5(10) . . . . ? O14 C81 Zn2 O13 172.3(4) . . . . ? C82 C81 Zn2 O13 -41.5(9) . . . . ? O14 C81 Zn2 O10 -4.4(3) . . . . ? O13 C81 Zn2 O10 -176.7(2) . . . . ? C82 C81 Zn2 O10 141.7(10) . . . . ? C36 N13 Zn3 N5 30.5(4) . . . . ? C37 N13 Zn3 N5 -160.4(3) . . . . ? C36 N13 Zn3 O12 156.5(4) . . . . ? C37 N13 Zn3 O12 -34.3(3) . . . . ? C36 N13 Zn3 O15 -83.3(4) . . . 1_455 ? C37 N13 Zn3 O15 85.9(4) . . . 1_455 ? C36 N13 Zn3 O16 -66.7(4) . . . 1_455 ? C37 N13 Zn3 O16 102.4(3) . . . 1_455 ? C15 N5 Zn3 N13 39.3(4) . . . . ? C16 N5 Zn3 N13 -146.9(3) . . . . ? C15 N5 Zn3 O12 -67.3(4) . . . . ? C16 N5 Zn3 O12 106.5(3) . . . . ? C15 N5 Zn3 O15 -179.7(4) . . . 1_455 ? C16 N5 Zn3 O15 -5.9(3) . . . 1_455 ? C15 N5 Zn3 O16 126.9(4) . . . 1_455 ? C16 N5 Zn3 O16 -59.3(3) . . . 1_455 ? C72 O12 Zn3 N13 120.4(3) . . . . ? C72 O12 Zn3 N5 -121.3(3) . . . . ? C72 O12 Zn3 O15 -20.5(4) . . . 1_455 ? C72 O12 Zn3 O16 38.0(4) . . . 1_455 ? C39 N15 Zn4 O4 -159.8(4) . . . 1_455 ? C40 N15 Zn4 O4 26.1(3) . . . 1_455 ? C39 N15 Zn4 N7 -38.9(4) . . . . ? C40 N15 Zn4 N7 147.0(3) . . . . ? C39 N15 Zn4 O8 72.8(4) . . . . ? C40 N15 Zn4 O8 -101.3(3) . . . . ? C26 N7 Zn4 O4 77.6(4) . . . 1_455 ? C28 N7 Zn4 O4 -102.0(3) . . . 1_455 ? C26 N7 Zn4 N15 -38.1(4) . . . . ? C28 N7 Zn4 N15 142.4(3) . . . . ? C26 N7 Zn4 O8 -171.0(4) . . . . ? C28 N7 Zn4 O8 9.5(4) . . . . ? C64 O8 Zn4 O4 -146.0(3) . . . 1_455 ? C64 O8 Zn4 N15 -21.1(3) . . . . ? C64 O8 Zn4 N7 100.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C12 H12 O5 0.93 2.08 2.918(5) 149.8 3_665 C17 H17 O3 0.93 2.29 3.216(5) 173.9 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.256 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 963193' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C41 H21 F12 N2 O8 S Zn2' _chemical_formula_sum 'C41 H21 F12 N2 O8 S Zn2' _chemical_formula_weight 1060.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 21.330(3) _cell_length_b 8.1009(13) _cell_length_c 30.993(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.460(7) _cell_angle_gamma 90.00 _cell_volume 4518.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7004 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.65 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2116 _exptl_absorpt_coefficient_mu 1.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7284 _exptl_absorpt_correction_T_max 0.8301 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28076 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 27.10 _reflns_number_total 9981 _reflns_number_gt 6588 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0900P] 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 9981 _refine_ls_number_parameters 595 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.012 _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 C1 C 0.58766(18) 1.0104(4) 0.65481(13) 0.0489(8) Uani 1 1 d . . . C2 C 0.51082(18) 1.0040(4) 0.64503(12) 0.0484(8) Uani 1 1 d . . . C3 C 0.47373(17) 0.8559(4) 0.63553(12) 0.0497(8) Uani 1 1 d . . . H3 H 0.4954 0.7589 0.6336 0.060 Uiso 1 1 calc R . . C4 C 0.40445(18) 0.8518(4) 0.62884(12) 0.0516(8) Uani 1 1 d . . . H4 H 0.3807 0.7509 0.6239 0.062 Uiso 1 1 calc R . . C5 C 0.36966(17) 0.9949(4) 0.62942(12) 0.0498(8) Uani 1 1 d . . . C6 C 0.4063(2) 1.1439(4) 0.63737(17) 0.0692(11) Uani 1 1 d . . . H6 H 0.3831 1.2421 0.6365 0.083 Uiso 1 1 calc R . . C7 C 0.4774(2) 1.1468(4) 0.64654(17) 0.0716(11) Uani 1 1 d . . . H7 H 0.5028 1.2465 0.6538 0.086 Uiso 1 1 calc R . . C8 C 0.29030(18) 0.9800(4) 0.61865(13) 0.0530(8) Uani 1 1 d . . . C9 C 0.2388(2) 0.9406(6) 0.56168(16) 0.0725(11) Uani 1 1 d . . . C10 C 0.2629(2) 1.1388(6) 0.6296(2) 0.0791(12) Uani 1 1 d . . . C11 C 0.28929(17) 0.8454(4) 0.65377(12) 0.0468(7) Uani 1 1 d . . . C12 C 0.23425(18) 0.7275(4) 0.63728(13) 0.0537(8) Uani 1 1 d . . . H12 H 0.1953 0.7253 0.6032 0.064 Uiso 1 1 calc R . . C13 C 0.23673(18) 0.6125(4) 0.67125(13) 0.0531(8) Uani 1 1 d . . . H13 H 0.1996 0.5330 0.6595 0.064 Uiso 1 1 calc R . . C14 C 0.29294(18) 0.6136(4) 0.72199(13) 0.0480(8) Uani 1 1 d . . . C15 C 0.3478(2) 0.7326(4) 0.73893(14) 0.0591(9) Uani 1 1 d . . . H15 H 0.3858 0.7365 0.7733 0.071 Uiso 1 1 calc R . . C16 C 0.3461(2) 0.8469(4) 0.70467(13) 0.0586(9) Uani 1 1 d . . . H16 H 0.3837 0.9251 0.7163 0.070 Uiso 1 1 calc R . . C17 C 0.2974(2) 0.4891(4) 0.75949(15) 0.0548(9) Uani 1 1 d . . . C18 C 0.81222(18) 0.8807(4) 0.74728(13) 0.0481(7) Uani 1 1 d . . . C19 C 0.87518(17) 0.7929(4) 0.79212(12) 0.0455(7) Uani 1 1 d . . . C20 C 0.89241(17) 0.6328(4) 0.78686(12) 0.0464(7) Uani 1 1 d . . . H20 H 0.8656 0.5807 0.7552 0.056 Uiso 1 1 calc R . . C21 C 0.94868(18) 0.5509(4) 0.82799(12) 0.0475(7) Uani 1 1 d . . . H21 H 0.9599 0.4435 0.8238 0.057 Uiso 1 1 calc R . . C22 C 0.98916(17) 0.6234(4) 0.87556(11) 0.0455(7) Uani 1 1 d . . . C23 C 0.97143(19) 0.7847(4) 0.88051(13) 0.0552(8) Uani 1 1 d . . . H23 H 0.9980 0.8363 0.9122 0.066 Uiso 1 1 calc R . . C24 C 0.91578(19) 0.8685(4) 0.83963(13) 0.0564(8) Uani 1 1 d . . . H24 H 0.9050 0.9766 0.8436 0.068 Uiso 1 1 calc R . . C25 C 1.04805(19) 0.5191(4) 0.92059(12) 0.0526(8) Uani 1 1 d . . . C26 C 1.0047(2) 0.4034(5) 0.93543(15) 0.0687(11) Uani 1 1 d . . . C27 C 1.1031(2) 0.6237(6) 0.96707(14) 0.0749(12) Uani 1 1 d . . . C28 C 1.09649(17) 0.4206(4) 0.90622(11) 0.0449(7) Uani 1 1 d . . . C29 C 1.11842(17) 0.4993(4) 0.87687(12) 0.0480(7) Uani 1 1 d . . . H29 H 1.1023 0.6063 0.8655 0.058 Uiso 1 1 calc R . . C30 C 1.16382(17) 0.4210(4) 0.86434(12) 0.0479(7) Uani 1 1 d . . . H30 H 1.1787 0.4760 0.8449 0.057 Uiso 1 1 calc R . . C31 C 1.18738(17) 0.2614(4) 0.88041(11) 0.0422(7) Uani 1 1 d . . . C32 C 1.16490(19) 0.1815(4) 0.90940(12) 0.0527(8) Uani 1 1 d . . . H32 H 1.1800 0.0736 0.9202 0.063 Uiso 1 1 calc R . . C33 C 1.1204(2) 0.2611(4) 0.92221(13) 0.0541(9) Uani 1 1 d . . . H33 H 1.1060 0.2067 0.9420 0.065 Uiso 1 1 calc R . . C34 C 1.23530(17) 0.1761(4) 0.86588(12) 0.0463(7) Uani 1 1 d . . . C35 C 0.64536(17) 0.5515(4) 0.58423(12) 0.0455(7) Uani 1 1 d . . . H35 H 0.6309 0.5127 0.6058 0.055 Uiso 1 1 calc R . . C36 C 0.6901(2) 0.7035(4) 0.55024(13) 0.0576(9) Uani 1 1 d . . . H36 H 0.7125 0.7916 0.5444 0.069 Uiso 1 1 calc R . . C37 C 0.6652(2) 0.5668(4) 0.52219(14) 0.0621(10) Uani 1 1 d . . . H37 H 0.6671 0.5423 0.4936 0.075 Uiso 1 1 calc R . . C38 C 0.60320(19) 0.3116(4) 0.52568(12) 0.0503(8) Uani 1 1 d . . . C39 C 0.6208(2) 0.1998(4) 0.50192(14) 0.0639(10) Uani 1 1 d . . . H39 H 0.6575 0.2150 0.4948 0.077 Uiso 1 1 calc R . . C40 C 0.5769(2) 0.0568(4) 0.48911(13) 0.0632(10) Uani 1 1 d . . . H40 H 0.5820 -0.0333 0.4726 0.076 Uiso 1 1 calc R . . C41 C 0.5266(2) 0.0623(4) 0.50300(12) 0.0549(8) Uani 1 1 d . . . F1 F 0.25142(14) 1.0421(4) 0.53271(9) 0.0995(8) Uani 1 1 d . . . F2 F 0.24938(13) 0.7884(3) 0.55018(8) 0.0804(7) Uani 1 1 d . . . F3 F 0.16642(12) 0.9518(4) 0.54365(9) 0.1007(9) Uani 1 1 d . . . F4 F 0.25121(16) 1.2614(3) 0.59704(12) 0.1071(9) Uani 1 1 d . . . F5 F 0.31186(16) 1.1967(3) 0.67666(12) 0.0887(7) Uani 1 1 d . . . F6 F 0.19917(14) 1.1174(3) 0.62717(12) 0.1047(9) Uani 1 1 d . . . F7 F 0.95458(14) 0.4881(3) 0.93925(9) 0.0914(8) Uani 1 1 d . . . F8 F 0.96895(14) 0.2857(3) 0.90087(9) 0.0793(6) Uani 1 1 d . . . F9 F 1.04884(15) 0.3283(3) 0.98080(9) 0.0917(8) Uani 1 1 d . . . F10 F 1.07261(15) 0.6960(3) 0.99025(8) 0.0926(8) Uani 1 1 d . . . F11 F 1.13258(13) 0.7426(3) 0.95415(9) 0.0846(7) Uani 1 1 d . . . F12 F 1.15970(15) 0.5336(3) 1.00274(8) 0.1063(9) Uani 1 1 d . . . N1 N 0.67749(14) 0.6941(3) 0.58911(10) 0.0454(6) Uani 1 1 d . . . N2 N 0.63623(15) 0.4688(3) 0.54343(9) 0.0481(6) Uani 1 1 d . . . O1 O 0.60460(12) 0.9042(3) 0.63350(9) 0.0543(6) Uani 1 1 d . . . O2 O 0.62942(13) 1.1216(3) 0.68424(11) 0.0732(7) Uani 1 1 d . . . O3 O 0.24922(13) 0.3735(3) 0.73886(10) 0.0608(6) Uani 1 1 d . . . O4 O 0.34420(18) 0.5010(3) 0.80549(11) 0.0837(8) Uani 1 1 d . . . O5 O 0.77778(13) 0.8026(3) 0.70698(9) 0.0605(6) Uani 1 1 d . . . O6 O 0.79979(15) 1.0261(3) 0.75427(10) 0.0754(7) Uani 1 1 d U . . O7 O 1.25639(13) 0.0321(3) 0.88165(9) 0.0581(6) Uani 1 1 d . . . O8 O 1.24997(15) 0.2550(3) 0.83778(11) 0.0684(7) Uani 1 1 d . . . S1 S 0.53264(6) 0.24778(10) 0.53249(4) 0.0647(3) Uani 1 1 d . . . Zn1 Zn 0.698323(19) 0.86962(4) 0.639995(13) 0.04009(10) Uani 1 1 d . . . Zn2 Zn 0.72876(2) 1.19996(4) 0.713702(14) 0.04257(10) 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 C1 0.0406(18) 0.0510(19) 0.052(2) 0.0096(15) 0.0230(17) -0.0037(15) C2 0.0446(18) 0.0502(19) 0.055(2) 0.0032(15) 0.0299(17) -0.0039(14) C3 0.0447(18) 0.0517(18) 0.054(2) -0.0018(15) 0.0277(17) -0.0016(15) C4 0.0478(19) 0.0512(18) 0.055(2) 0.0025(15) 0.0276(17) -0.0073(15) C5 0.0427(18) 0.058(2) 0.053(2) 0.0147(15) 0.0282(17) 0.0049(15) C6 0.062(2) 0.049(2) 0.115(3) 0.012(2) 0.059(3) 0.0039(18) C7 0.066(2) 0.049(2) 0.117(3) 0.004(2) 0.061(3) -0.0090(18) C8 0.0432(18) 0.062(2) 0.060(2) 0.0167(16) 0.0318(18) 0.0033(16) C9 0.049(2) 0.099(3) 0.062(3) 0.032(2) 0.026(2) 0.005(2) C10 0.060(3) 0.080(3) 0.110(4) 0.031(3) 0.054(3) 0.017(2) C11 0.0398(17) 0.0575(19) 0.0474(19) 0.0090(14) 0.0263(16) 0.0020(15) C12 0.0385(18) 0.068(2) 0.051(2) 0.0109(16) 0.0217(17) -0.0012(16) C13 0.0428(18) 0.059(2) 0.061(2) 0.0028(16) 0.0304(18) -0.0079(15) C14 0.054(2) 0.0436(17) 0.057(2) 0.0033(14) 0.0372(18) 0.0001(15) C15 0.065(2) 0.063(2) 0.046(2) 0.0008(16) 0.0283(19) -0.0104(18) C16 0.063(2) 0.060(2) 0.054(2) -0.0001(16) 0.032(2) -0.0175(18) C17 0.063(2) 0.051(2) 0.063(2) 0.0124(17) 0.042(2) 0.0076(17) C18 0.0439(18) 0.0482(18) 0.055(2) 0.0026(16) 0.0288(17) 0.0029(15) C19 0.0434(18) 0.0478(18) 0.0466(19) 0.0028(14) 0.0250(16) 0.0060(14) C20 0.0449(18) 0.0503(18) 0.0413(18) -0.0054(14) 0.0214(15) 0.0036(15) C21 0.055(2) 0.0450(17) 0.0446(19) -0.0041(14) 0.0285(17) 0.0110(15) C22 0.0453(17) 0.0520(18) 0.0403(17) -0.0056(14) 0.0237(15) 0.0087(15) C23 0.052(2) 0.058(2) 0.0433(19) -0.0125(15) 0.0173(17) 0.0115(16) C24 0.055(2) 0.0474(18) 0.061(2) -0.0102(16) 0.0272(19) 0.0103(16) C25 0.059(2) 0.063(2) 0.0385(18) -0.0050(15) 0.0281(17) 0.0159(16) C26 0.082(3) 0.088(3) 0.060(2) 0.018(2) 0.054(2) 0.031(2) C27 0.072(3) 0.082(3) 0.047(2) -0.011(2) 0.016(2) 0.025(2) C28 0.0445(18) 0.0537(18) 0.0361(17) -0.0006(13) 0.0213(15) 0.0119(14) C29 0.0468(18) 0.0431(17) 0.054(2) 0.0045(14) 0.0265(17) 0.0098(14) C30 0.0530(19) 0.0452(17) 0.053(2) 0.0069(14) 0.0339(17) 0.0088(15) C31 0.0428(18) 0.0436(16) 0.0414(17) 0.0013(13) 0.0232(15) 0.0083(13) C32 0.065(2) 0.0503(18) 0.052(2) 0.0147(15) 0.0371(19) 0.0213(16) C33 0.075(2) 0.0526(19) 0.051(2) 0.0138(15) 0.044(2) 0.0190(17) C34 0.0410(17) 0.0486(18) 0.0495(19) -0.0030(14) 0.0244(16) 0.0048(14) C35 0.0459(18) 0.0407(17) 0.0473(19) -0.0046(13) 0.0232(16) -0.0048(14) C36 0.074(2) 0.0439(18) 0.059(2) -0.0032(16) 0.039(2) -0.0097(17) C37 0.089(3) 0.053(2) 0.055(2) -0.0117(17) 0.046(2) -0.0168(19) C38 0.058(2) 0.0354(16) 0.0459(19) -0.0064(13) 0.0202(17) -0.0069(15) C39 0.080(3) 0.0485(19) 0.059(2) -0.0159(16) 0.035(2) -0.0118(18) C40 0.079(3) 0.0408(18) 0.056(2) -0.0155(16) 0.027(2) -0.0049(18) C41 0.064(2) 0.0359(16) 0.0411(19) -0.0067(14) 0.0127(17) -0.0065(15) F1 0.0777(17) 0.144(2) 0.0710(16) 0.0503(15) 0.0360(14) 0.0023(15) F2 0.0623(14) 0.116(2) 0.0516(13) 0.0040(12) 0.0231(12) -0.0103(14) F3 0.0387(12) 0.157(2) 0.0832(18) 0.0395(16) 0.0175(12) 0.0097(14) F4 0.105(2) 0.0824(16) 0.161(3) 0.0620(17) 0.090(2) 0.0406(15) F5 0.101(2) 0.0681(14) 0.128(2) 0.0002(14) 0.082(2) 0.0089(14) F6 0.0822(17) 0.0981(18) 0.175(3) 0.0338(17) 0.096(2) 0.0284(14) F7 0.1026(19) 0.1191(19) 0.0931(18) 0.0230(14) 0.0794(17) 0.0436(15) F8 0.0903(17) 0.0830(16) 0.0892(17) 0.0002(13) 0.0646(16) -0.0052(13) F9 0.115(2) 0.1210(19) 0.0658(15) 0.0353(13) 0.0664(16) 0.0528(16) F10 0.112(2) 0.1104(18) 0.0489(13) -0.0197(12) 0.0386(14) 0.0340(15) F11 0.0684(16) 0.0848(16) 0.0780(17) -0.0317(13) 0.0242(14) -0.0038(13) F12 0.0944(19) 0.119(2) 0.0484(14) -0.0167(13) 0.0003(13) 0.0471(16) N1 0.0503(16) 0.0373(13) 0.0495(16) -0.0052(11) 0.0275(14) -0.0059(12) N2 0.0586(17) 0.0363(13) 0.0434(15) -0.0074(11) 0.0233(14) -0.0055(12) O1 0.0401(12) 0.0636(14) 0.0597(15) -0.0033(11) 0.0271(12) -0.0016(11) O2 0.0490(14) 0.0731(17) 0.103(2) -0.0259(15) 0.0440(16) -0.0208(13) O3 0.0600(15) 0.0510(13) 0.0751(17) 0.0173(12) 0.0386(14) 0.0037(12) O4 0.106(2) 0.0830(19) 0.0592(19) 0.0137(14) 0.0423(19) -0.0091(16) O5 0.0555(15) 0.0551(14) 0.0535(15) 0.0032(11) 0.0176(13) 0.0052(11) O6 0.0743(14) 0.0588(13) 0.0729(14) 0.0016(11) 0.0261(11) 0.0169(11) O7 0.0693(16) 0.0544(14) 0.0618(15) 0.0114(11) 0.0425(14) 0.0241(12) O8 0.096(2) 0.0475(13) 0.105(2) -0.0002(13) 0.0832(19) 0.0015(13) S1 0.0747(7) 0.0376(4) 0.0799(7) -0.0180(4) 0.0403(6) -0.0127(4) Zn1 0.03857(19) 0.03536(18) 0.0451(2) -0.00583(14) 0.02166(17) -0.00568(15) Zn2 0.0420(2) 0.03576(18) 0.0519(2) -0.00364(15) 0.02642(18) -0.00172(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.250(4) . ? C1 O2 1.251(4) . ? C1 C2 1.499(4) . ? C2 C7 1.372(5) . ? C2 C3 1.379(4) . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.382(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(5) . ? C5 C8 1.544(4) . ? C6 C7 1.386(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.524(5) . ? C8 C9 1.531(5) . ? C8 C11 1.549(4) . ? C9 F3 1.333(4) . ? C9 F2 1.336(5) . ? C9 F1 1.347(4) . ? C10 F6 1.333(4) . ? C10 F4 1.340(5) . ? C10 F5 1.343(5) . ? C11 C12 1.381(4) . ? C11 C16 1.380(4) . ? C12 C13 1.386(4) . ? C12 H12 0.9300 . ? C13 C14 1.373(5) . ? C13 H13 0.9300 . ? C14 C15 1.383(5) . ? C14 C17 1.503(4) . ? C15 C16 1.394(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O4 1.229(4) . ? C17 O3 1.279(4) . ? C18 O5 1.231(4) . ? C18 O6 1.252(4) . ? C18 C19 1.496(4) . ? C19 C20 1.381(4) . ? C19 C24 1.387(5) . ? C20 C21 1.365(4) . ? C20 H20 0.9300 . ? C21 C22 1.378(4) . ? C21 H21 0.9300 . ? C22 C23 1.392(4) . ? C22 C25 1.535(4) . ? C23 C24 1.364(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C27 1.535(5) . ? C25 C28 1.548(4) . ? C25 C26 1.549(5) . ? C26 F7 1.328(4) . ? C26 F8 1.327(5) . ? C26 F9 1.346(4) . ? C27 F11 1.325(5) . ? C27 F12 1.334(4) . ? C27 F10 1.336(4) . ? C28 C33 1.379(4) . ? C28 C29 1.382(4) . ? C29 C30 1.376(4) . ? C29 H29 0.9300 . ? C30 C31 1.380(4) . ? C30 H30 0.9300 . ? C31 C32 1.385(4) . ? C31 C34 1.490(4) . ? C32 C33 1.372(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 O8 1.248(4) . ? C34 O7 1.251(4) . ? C35 N1 1.310(4) . ? C35 N2 1.350(4) . ? C35 H35 0.9300 . ? C36 C37 1.330(5) . ? C36 N1 1.370(4) . ? C36 H36 0.9300 . ? C37 N2 1.372(4) . ? C37 H37 0.9300 . ? C38 C39 1.342(4) . ? C38 N2 1.416(4) . ? C38 S1 1.708(3) . ? C39 C40 1.405(5) . ? C39 H39 0.9300 . ? C40 C41 1.354(5) . ? C40 H40 0.9300 . ? C41 C41 1.455(7) 3_656 ? C41 S1 1.727(3) . ? N1 Zn1 1.988(2) . ? O1 Zn1 1.919(2) . ? O2 Zn2 1.910(2) . ? O3 Zn2 1.902(2) 2_646 ? O5 Zn1 1.924(2) . ? O6 Zn2 1.953(3) . ? O7 Zn1 1.952(2) 2_746 ? O8 Zn2 1.931(2) 2_746 ? Zn1 O7 1.952(2) 2_766 ? Zn2 O3 1.902(2) 2_666 ? Zn2 O8 1.931(2) 2_766 ? 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 C1 O2 125.9(3) . . ? O1 C1 C2 117.7(3) . . ? O2 C1 C2 116.5(3) . . ? C7 C2 C3 119.5(3) . . ? C7 C2 C1 119.7(3) . . ? C3 C2 C1 120.8(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 118.5(3) . . ? C4 C5 C8 117.8(3) . . ? C6 C5 C8 123.7(3) . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C2 C7 C6 120.6(3) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C10 C8 C9 108.0(3) . . ? C10 C8 C5 113.1(3) . . ? C9 C8 C5 106.9(3) . . ? C10 C8 C11 106.7(3) . . ? C9 C8 C11 113.1(3) . . ? C5 C8 C11 109.3(3) . . ? F3 C9 F2 105.9(4) . . ? F3 C9 F1 106.3(3) . . ? F2 C9 F1 105.2(3) . . ? F3 C9 C8 115.0(3) . . ? F2 C9 C8 112.3(3) . . ? F1 C9 C8 111.4(3) . . ? F6 C10 F4 106.4(3) . . ? F6 C10 F5 106.3(4) . . ? F4 C10 F5 106.3(4) . . ? F6 C10 C8 112.2(4) . . ? F4 C10 C8 113.4(4) . . ? F5 C10 C8 111.7(3) . . ? C12 C11 C16 118.6(3) . . ? C12 C11 C8 123.8(3) . . ? C16 C11 C8 117.5(3) . . ? C11 C12 C13 120.4(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 118.7(3) . . ? C13 C14 C17 122.3(3) . . ? C15 C14 C17 119.0(3) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.9(3) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? O4 C17 O3 124.9(3) . . ? O4 C17 C14 121.3(3) . . ? O3 C17 C14 113.9(3) . . ? O5 C18 O6 126.4(3) . . ? O5 C18 C19 116.6(3) . . ? O6 C18 C19 117.0(3) . . ? C20 C19 C24 119.1(3) . . ? C20 C19 C18 120.0(3) . . ? C24 C19 C18 120.9(3) . . ? C21 C20 C19 120.2(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 121.6(3) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C21 C22 C23 117.8(3) . . ? C21 C22 C25 118.4(3) . . ? C23 C22 C25 123.7(3) . . ? C24 C23 C22 121.2(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C19 120.2(3) . . ? C23 C24 H24 119.9 . . ? C19 C24 H24 119.9 . . ? C22 C25 C27 113.0(3) . . ? C22 C25 C28 111.7(2) . . ? C27 C25 C28 105.2(3) . . ? C22 C25 C26 106.0(3) . . ? C27 C25 C26 109.4(3) . . ? C28 C25 C26 111.7(3) . . ? F7 C26 F8 107.5(3) . . ? F7 C26 F9 106.6(3) . . ? F8 C26 F9 107.2(3) . . ? F7 C26 C25 110.6(3) . . ? F8 C26 C25 111.8(3) . . ? F9 C26 C25 112.9(3) . . ? F11 C27 F12 106.4(4) . . ? F11 C27 F10 106.9(3) . . ? F12 C27 F10 106.2(3) . . ? F11 C27 C25 111.5(3) . . ? F12 C27 C25 111.9(3) . . ? F10 C27 C25 113.5(4) . . ? C33 C28 C29 118.6(3) . . ? C33 C28 C25 123.6(3) . . ? C29 C28 C25 117.7(3) . . ? C30 C29 C28 120.8(3) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 120.3(3) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C30 C31 C32 119.1(3) . . ? C30 C31 C34 120.1(3) . . ? C32 C31 C34 120.8(3) . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C28 121.1(3) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? O8 C34 O7 125.3(3) . . ? O8 C34 C31 116.3(3) . . ? O7 C34 C31 118.4(3) . . ? N1 C35 N2 110.5(3) . . ? N1 C35 H35 124.8 . . ? N2 C35 H35 124.8 . . ? C37 C36 N1 109.3(3) . . ? C37 C36 H36 125.3 . . ? N1 C36 H36 125.3 . . ? C36 C37 N2 107.0(3) . . ? C36 C37 H37 126.5 . . ? N2 C37 H37 126.5 . . ? C39 C38 N2 126.4(3) . . ? C39 C38 S1 112.8(3) . . ? N2 C38 S1 120.8(2) . . ? C38 C39 C40 111.8(3) . . ? C38 C39 H39 124.1 . . ? C40 C39 H39 124.1 . . ? C41 C40 C39 113.8(3) . . ? C41 C40 H40 123.1 . . ? C39 C40 H40 123.1 . . ? C40 C41 C41 129.3(4) . 3_656 ? C40 C41 S1 110.5(3) . . ? C41 C41 S1 120.2(4) 3_656 . ? C35 N1 C36 106.5(3) . . ? C35 N1 Zn1 127.0(2) . . ? C36 N1 Zn1 126.3(2) . . ? C35 N2 C37 106.7(2) . . ? C35 N2 C38 127.0(3) . . ? C37 N2 C38 126.3(3) . . ? C1 O1 Zn1 128.7(2) . . ? C1 O2 Zn2 139.5(2) . . ? C17 O3 Zn2 110.9(2) . 2_646 ? C18 O5 Zn1 130.6(2) . . ? C18 O6 Zn2 136.9(2) . . ? C34 O7 Zn1 129.41(19) . 2_746 ? C34 O8 Zn2 135.8(2) . 2_746 ? C38 S1 C41 91.04(16) . . ? O1 Zn1 O5 114.78(10) . . ? O1 Zn1 O7 123.02(10) . 2_766 ? O5 Zn1 O7 104.44(11) . 2_766 ? O1 Zn1 N1 104.16(10) . . ? O5 Zn1 N1 110.28(11) . . ? O7 Zn1 N1 98.67(9) 2_766 . ? O3 Zn2 O2 111.44(10) 2_666 . ? O3 Zn2 O8 113.45(10) 2_666 2_766 ? O2 Zn2 O8 111.97(12) . 2_766 ? O3 Zn2 O6 104.53(11) 2_666 . ? O2 Zn2 O6 110.26(12) . . ? O8 Zn2 O6 104.68(11) 2_766 . ? 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 C1 C2 C7 -150.6(3) . . . . ? O2 C1 C2 C7 30.1(5) . . . . ? O1 C1 C2 C3 30.7(4) . . . . ? O2 C1 C2 C3 -148.6(3) . . . . ? C7 C2 C3 C4 -1.5(5) . . . . ? C1 C2 C3 C4 177.2(3) . . . . ? C2 C3 C4 C5 2.6(5) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C3 C4 C5 C8 176.7(3) . . . . ? C4 C5 C6 C7 -2.6(6) . . . . ? C8 C5 C6 C7 -179.6(3) . . . . ? C3 C2 C7 C6 -1.6(6) . . . . ? C1 C2 C7 C6 179.7(3) . . . . ? C5 C6 C7 C2 3.7(6) . . . . ? C4 C5 C8 C10 169.7(3) . . . . ? C6 C5 C8 C10 -13.2(5) . . . . ? C4 C5 C8 C9 -71.6(4) . . . . ? C6 C5 C8 C9 105.5(4) . . . . ? C4 C5 C8 C11 51.0(4) . . . . ? C6 C5 C8 C11 -131.8(3) . . . . ? C10 C8 C9 F3 -46.9(4) . . . . ? C5 C8 C9 F3 -168.8(3) . . . . ? C11 C8 C9 F3 70.9(4) . . . . ? C10 C8 C9 F2 -168.1(3) . . . . ? C5 C8 C9 F2 69.9(3) . . . . ? C11 C8 C9 F2 -50.4(4) . . . . ? C10 C8 C9 F1 74.1(4) . . . . ? C5 C8 C9 F1 -47.8(4) . . . . ? C11 C8 C9 F1 -168.1(3) . . . . ? C9 C8 C10 F6 70.9(4) . . . . ? C5 C8 C10 F6 -171.0(3) . . . . ? C11 C8 C10 F6 -50.9(5) . . . . ? C9 C8 C10 F4 -49.7(4) . . . . ? C5 C8 C10 F4 68.4(5) . . . . ? C11 C8 C10 F4 -171.5(3) . . . . ? C9 C8 C10 F5 -169.8(3) . . . . ? C5 C8 C10 F5 -51.7(4) . . . . ? C11 C8 C10 F5 68.4(4) . . . . ? C10 C8 C11 C12 101.3(4) . . . . ? C9 C8 C11 C12 -17.2(4) . . . . ? C5 C8 C11 C12 -136.2(3) . . . . ? C10 C8 C11 C16 -77.2(4) . . . . ? C9 C8 C11 C16 164.3(3) . . . . ? C5 C8 C11 C16 45.4(4) . . . . ? C16 C11 C12 C13 -0.6(5) . . . . ? C8 C11 C12 C13 -179.1(3) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C12 C13 C14 C17 -179.3(3) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? C17 C14 C15 C16 178.3(3) . . . . ? C12 C11 C16 C15 -0.4(5) . . . . ? C8 C11 C16 C15 178.1(3) . . . . ? C14 C15 C16 C11 1.2(5) . . . . ? C13 C14 C17 O4 -173.4(3) . . . . ? C15 C14 C17 O4 7.3(5) . . . . ? C13 C14 C17 O3 7.1(4) . . . . ? C15 C14 C17 O3 -172.1(3) . . . . ? O5 C18 C19 C20 0.5(4) . . . . ? O6 C18 C19 C20 -179.3(3) . . . . ? O5 C18 C19 C24 -177.8(3) . . . . ? O6 C18 C19 C24 2.4(5) . . . . ? C24 C19 C20 C21 0.0(5) . . . . ? C18 C19 C20 C21 -178.4(3) . . . . ? C19 C20 C21 C22 0.6(5) . . . . ? C20 C21 C22 C23 -0.6(5) . . . . ? C20 C21 C22 C25 176.0(3) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C25 C22 C23 C24 -176.4(3) . . . . ? C22 C23 C24 C19 0.6(5) . . . . ? C20 C19 C24 C23 -0.6(5) . . . . ? C18 C19 C24 C23 177.8(3) . . . . ? C21 C22 C25 C27 164.0(3) . . . . ? C23 C22 C25 C27 -19.6(5) . . . . ? C21 C22 C25 C28 45.7(4) . . . . ? C23 C22 C25 C28 -137.9(3) . . . . ? C21 C22 C25 C26 -76.2(3) . . . . ? C23 C22 C25 C26 100.2(4) . . . . ? C22 C25 C26 F7 -47.8(4) . . . . ? C27 C25 C26 F7 74.3(4) . . . . ? C28 C25 C26 F7 -169.6(3) . . . . ? C22 C25 C26 F8 72.0(3) . . . . ? C27 C25 C26 F8 -165.9(3) . . . . ? C28 C25 C26 F8 -49.8(4) . . . . ? C22 C25 C26 F9 -167.1(3) . . . . ? C27 C25 C26 F9 -45.0(4) . . . . ? C28 C25 C26 F9 71.1(4) . . . . ? C22 C25 C27 F11 -52.0(4) . . . . ? C28 C25 C27 F11 70.1(4) . . . . ? C26 C25 C27 F11 -169.8(3) . . . . ? C22 C25 C27 F12 -171.0(3) . . . . ? C28 C25 C27 F12 -49.0(4) . . . . ? C26 C25 C27 F12 71.2(4) . . . . ? C22 C25 C27 F10 68.8(4) . . . . ? C28 C25 C27 F10 -169.2(3) . . . . ? C26 C25 C27 F10 -49.0(4) . . . . ? C22 C25 C28 C33 -141.0(3) . . . . ? C27 C25 C28 C33 96.1(4) . . . . ? C26 C25 C28 C33 -22.5(5) . . . . ? C22 C25 C28 C29 40.8(4) . . . . ? C27 C25 C28 C29 -82.1(4) . . . . ? C26 C25 C28 C29 159.3(3) . . . . ? C33 C28 C29 C30 -0.7(5) . . . . ? C25 C28 C29 C30 177.6(3) . . . . ? C28 C29 C30 C31 0.9(5) . . . . ? C29 C30 C31 C32 -0.2(5) . . . . ? C29 C30 C31 C34 178.8(3) . . . . ? C30 C31 C32 C33 -0.6(5) . . . . ? C34 C31 C32 C33 -179.6(3) . . . . ? C31 C32 C33 C28 0.7(5) . . . . ? C29 C28 C33 C32 0.0(5) . . . . ? C25 C28 C33 C32 -178.2(3) . . . . ? C30 C31 C34 O8 -2.1(5) . . . . ? C32 C31 C34 O8 176.8(3) . . . . ? C30 C31 C34 O7 179.1(3) . . . . ? C32 C31 C34 O7 -1.9(5) . . . . ? N1 C36 C37 N2 0.1(4) . . . . ? N2 C38 C39 C40 -179.6(3) . . . . ? S1 C38 C39 C40 -0.7(4) . . . . ? C38 C39 C40 C41 0.3(5) . . . . ? C39 C40 C41 C41 -178.7(4) . . . 3_656 ? C39 C40 C41 S1 0.2(4) . . . . ? N2 C35 N1 C36 -0.4(4) . . . . ? N2 C35 N1 Zn1 176.0(2) . . . . ? C37 C36 N1 C35 0.2(4) . . . . ? C37 C36 N1 Zn1 -176.3(3) . . . . ? N1 C35 N2 C37 0.5(4) . . . . ? N1 C35 N2 C38 -179.5(3) . . . . ? C36 C37 N2 C35 -0.3(4) . . . . ? C36 C37 N2 C38 179.6(3) . . . . ? C39 C38 N2 C35 -148.8(4) . . . . ? S1 C38 N2 C35 32.3(5) . . . . ? C39 C38 N2 C37 31.2(6) . . . . ? S1 C38 N2 C37 -147.7(3) . . . . ? O2 C1 O1 Zn1 2.5(5) . . . . ? C2 C1 O1 Zn1 -176.7(2) . . . . ? O1 C1 O2 Zn2 -0.4(6) . . . . ? C2 C1 O2 Zn2 178.8(3) . . . . ? O4 C17 O3 Zn2 -11.2(4) . . . 2_646 ? C14 C17 O3 Zn2 168.2(2) . . . 2_646 ? O6 C18 O5 Zn1 4.0(5) . . . . ? C19 C18 O5 Zn1 -175.79(19) . . . . ? O5 C18 O6 Zn2 0.9(6) . . . . ? C19 C18 O6 Zn2 -179.3(2) . . . . ? O8 C34 O7 Zn1 -12.0(5) . . . 2_746 ? C31 C34 O7 Zn1 166.5(2) . . . 2_746 ? O7 C34 O8 Zn2 28.3(6) . . . 2_746 ? C31 C34 O8 Zn2 -150.3(3) . . . 2_746 ? C39 C38 S1 C41 0.7(3) . . . . ? N2 C38 S1 C41 179.7(3) . . . . ? C40 C41 S1 C38 -0.4(3) . . . . ? C41 C41 S1 C38 178.5(4) 3_656 . . . ? C1 O1 Zn1 O5 64.8(3) . . . . ? C1 O1 Zn1 O7 -64.0(3) . . . 2_766 ? C1 O1 Zn1 N1 -174.5(3) . . . . ? C18 O5 Zn1 O1 -71.4(3) . . . . ? C18 O5 Zn1 O7 66.3(3) . . . 2_766 ? C18 O5 Zn1 N1 171.4(3) . . . . ? C35 N1 Zn1 O1 -51.5(3) . . . . ? C36 N1 Zn1 O1 124.2(3) . . . . ? C35 N1 Zn1 O5 72.1(3) . . . . ? C36 N1 Zn1 O5 -112.1(3) . . . . ? C35 N1 Zn1 O7 -178.9(3) . . . 2_766 ? C36 N1 Zn1 O7 -3.1(3) . . . 2_766 ? C1 O2 Zn2 O3 -175.0(4) . . . 2_666 ? C1 O2 Zn2 O8 56.8(4) . . . 2_766 ? C1 O2 Zn2 O6 -59.3(4) . . . . ? C18 O6 Zn2 O3 175.2(3) . . . 2_666 ? C18 O6 Zn2 O2 55.3(4) . . . . ? C18 O6 Zn2 O8 -65.3(4) . . . 2_766 ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.000 27.2 -0.3 2 1.000 -0.035 0.250 162.2 17.1 3 1.000 0.000 0.500 27.2 -0.4 4 1.000 0.019 0.750 162.2 17.0 5 0.500 0.455 0.750 103.4 5.3 6 0.500 0.545 0.250 103.3 4.9 7 0.466 0.503 0.089 21.8 1.1 8 0.534 0.503 0.411 22.3 1.6 9 0.466 0.497 0.589 21.8 0.9 10 0.534 0.497 0.911 22.2 1.4 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.435 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 963194' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 Cd N4 O4 S2' _chemical_formula_sum 'C22 H14 Cd N4 O4 S2' _chemical_formula_weight 574.89 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5686(8) _cell_length_b 10.3542(8) _cell_length_c 11.0911(9) _cell_angle_alpha 80.1480(10) _cell_angle_beta 83.5200(10) _cell_angle_gamma 72.5150(10) _cell_volume 1030.42(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5143 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.37 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_T_max 0.7993 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6814 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4506 _reflns_number_gt 4092 _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^)+(0.0418P)^2^+0.0100P] 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 4506 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Cd1 Cd 0.998701(17) -0.200768(14) 0.118521(13) 0.02822(7) Uani 1 1 d . . . S1 S 0.63955(7) 0.18419(8) 0.47418(7) 0.04494(17) Uani 1 1 d . . . S2 S 0.35002(7) 0.45558(8) 0.71559(7) 0.04755(18) Uani 1 1 d . . . O1 O 1.0753(2) -0.06627(17) 0.22108(16) 0.0415(4) Uani 1 1 d . . . O2 O 1.1123(2) 0.07911(17) 0.05674(15) 0.0430(4) Uani 1 1 d . . . O3 O 0.9736(2) 0.57918(16) 0.11722(15) 0.0386(4) Uani 1 1 d . . . O4 O 1.0312(2) 0.61684(16) 0.29191(16) 0.0392(4) Uani 1 1 d . . . N1 N 0.7658(2) -0.0993(2) 0.20032(18) 0.0370(5) Uani 1 1 d . . . N2 N 0.5952(2) 0.0369(2) 0.30866(18) 0.0333(4) Uani 1 1 d . . . N3 N 0.3853(2) 0.6084(2) 0.88025(17) 0.0321(4) Uani 1 1 d . . . N4 N 0.2158(2) 0.7228(2) 1.00494(18) 0.0358(4) Uani 1 1 d . . . C1 C 1.0863(2) 0.0488(2) 0.1689(2) 0.0284(4) Uani 1 1 d . . . C2 C 1.0639(2) 0.1566(2) 0.25087(19) 0.0261(4) Uani 1 1 d . . . C3 C 1.0556(2) 0.2925(2) 0.20241(19) 0.0261(4) Uani 1 1 d . . . H3 H 1.0714 0.3164 0.1184 0.031 Uiso 1 1 calc R . . C4 C 1.0238(2) 0.3919(2) 0.2790(2) 0.0253(4) Uani 1 1 d . . . C5 C 1.0004(2) 0.3558(2) 0.4052(2) 0.0296(5) Uani 1 1 d . . . H5 H 0.9781 0.4225 0.4565 0.036 Uiso 1 1 calc R . . C6 C 1.0100(3) 0.2213(2) 0.4547(2) 0.0312(5) Uani 1 1 d . . . H6 H 0.9953 0.1974 0.5389 0.037 Uiso 1 1 calc R . . C7 C 1.0418(3) 0.1226(2) 0.3774(2) 0.0295(5) Uani 1 1 d . . . H7 H 1.0485 0.0323 0.4105 0.035 Uiso 1 1 calc R . . C8 C 1.0088(2) 0.5395(2) 0.2258(2) 0.0269(4) Uani 1 1 d . . . C17 C 0.7406(3) -0.0172(3) 0.2830(2) 0.0362(5) Uani 1 1 d . . . H17 H 0.8138 0.0016 0.3195 0.043 Uiso 1 1 calc R . . C18 C 0.6303(3) -0.0979(3) 0.1706(2) 0.0440(6) Uani 1 1 d . . . H18 H 0.6141 -0.1468 0.1132 0.053 Uiso 1 1 calc R . . C19 C 0.5234(3) -0.0157(3) 0.2364(3) 0.0437(6) Uani 1 1 d . . . H19 H 0.4225 0.0018 0.2336 0.052 Uiso 1 1 calc R . . C20 C 0.5299(3) 0.1312(2) 0.3910(2) 0.0322(5) Uani 1 1 d . . . C21 C 0.3865(3) 0.1899(3) 0.4162(2) 0.0415(6) Uani 1 1 d . . . H21 H 0.3119 0.1736 0.3796 0.050 Uiso 1 1 calc R . . C22 C 0.3614(3) 0.2791(3) 0.5047(3) 0.0432(6) Uani 1 1 d . . . H22 H 0.2680 0.3270 0.5328 0.052 Uiso 1 1 calc R . . C23 C 0.4870(3) 0.2883(2) 0.5449(2) 0.0331(5) Uani 1 1 d . . . C24 C 0.5050(3) 0.3688(2) 0.6339(2) 0.0336(5) Uani 1 1 d . . . C25 C 0.6274(3) 0.3893(3) 0.6679(2) 0.0425(6) Uani 1 1 d . . . H25 H 0.7212 0.3506 0.6343 0.051 Uiso 1 1 calc R . . C26 C 0.5987(3) 0.4755(3) 0.7600(2) 0.0410(6) Uani 1 1 d . . . H26 H 0.6708 0.4996 0.7930 0.049 Uiso 1 1 calc R . . C27 C 0.4543(3) 0.5184(2) 0.7938(2) 0.0321(5) Uani 1 1 d . . . C28 C 0.2504(3) 0.6216(2) 0.9398(2) 0.0340(5) Uani 1 1 d . . . H28 H 0.1909 0.5666 0.9350 0.041 Uiso 1 1 calc R . . C29 C 0.4380(3) 0.7073(2) 0.9122(2) 0.0396(5) Uani 1 1 d . . . H29 H 0.5282 0.7228 0.8865 0.047 Uiso 1 1 calc R . . C30 C 0.3328(3) 0.7770(3) 0.9879(2) 0.0406(6) Uani 1 1 d . . . H30 H 0.3385 0.8503 1.0232 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.04007(11) 0.02039(9) 0.02440(10) -0.00891(6) 0.00544(7) -0.00857(7) S1 0.0275(3) 0.0545(4) 0.0580(4) -0.0354(3) 0.0070(3) -0.0080(3) S2 0.0283(3) 0.0568(4) 0.0648(4) -0.0402(4) 0.0097(3) -0.0103(3) O1 0.0678(12) 0.0264(8) 0.0363(9) -0.0119(7) 0.0031(8) -0.0206(8) O2 0.0650(12) 0.0335(9) 0.0251(8) -0.0101(7) 0.0000(8) -0.0039(8) O3 0.0622(11) 0.0270(8) 0.0286(8) -0.0043(7) 0.0008(8) -0.0172(8) O4 0.0583(11) 0.0249(8) 0.0411(9) -0.0067(7) -0.0108(8) -0.0182(8) N1 0.0438(12) 0.0323(10) 0.0311(10) -0.0101(8) 0.0063(9) -0.0051(9) N2 0.0354(10) 0.0323(10) 0.0318(10) -0.0122(8) 0.0054(8) -0.0077(8) N3 0.0337(10) 0.0320(10) 0.0306(10) -0.0107(8) 0.0030(8) -0.0082(8) N4 0.0398(11) 0.0351(11) 0.0333(10) -0.0139(9) 0.0056(9) -0.0099(9) C1 0.0327(11) 0.0254(10) 0.0278(10) -0.0093(9) -0.0012(9) -0.0069(9) C2 0.0289(11) 0.0252(10) 0.0264(10) -0.0080(8) -0.0006(8) -0.0089(8) C3 0.0311(11) 0.0246(10) 0.0233(10) -0.0054(8) 0.0010(8) -0.0089(8) C4 0.0266(10) 0.0221(10) 0.0294(10) -0.0076(8) -0.0018(8) -0.0079(8) C5 0.0325(11) 0.0290(11) 0.0315(11) -0.0137(9) -0.0008(9) -0.0103(9) C6 0.0395(12) 0.0326(12) 0.0233(10) -0.0062(9) 0.0010(9) -0.0130(10) C7 0.0393(12) 0.0235(10) 0.0278(11) -0.0038(8) -0.0007(9) -0.0127(9) C8 0.0277(11) 0.0202(10) 0.0332(11) -0.0080(9) 0.0035(9) -0.0072(8) C17 0.0347(12) 0.0383(13) 0.0321(12) -0.0128(10) 0.0030(10) -0.0029(10) C18 0.0538(16) 0.0421(14) 0.0414(14) -0.0189(12) 0.0043(12) -0.0175(12) C19 0.0421(14) 0.0474(15) 0.0484(15) -0.0218(12) 0.0044(12) -0.0174(12) C20 0.0337(12) 0.0297(11) 0.0334(12) -0.0109(9) 0.0050(9) -0.0087(9) C21 0.0318(12) 0.0476(15) 0.0480(15) -0.0225(12) 0.0002(11) -0.0079(11) C22 0.0294(12) 0.0480(15) 0.0511(15) -0.0248(13) 0.0042(11) -0.0023(11) C23 0.0292(11) 0.0318(12) 0.0367(12) -0.0111(10) 0.0056(9) -0.0057(9) C24 0.0301(11) 0.0327(12) 0.0359(12) -0.0120(10) 0.0056(9) -0.0051(9) C25 0.0291(12) 0.0534(16) 0.0444(14) -0.0224(12) 0.0058(11) -0.0056(11) C26 0.0313(12) 0.0551(16) 0.0393(13) -0.0212(12) 0.0002(10) -0.0092(11) C27 0.0325(12) 0.0310(11) 0.0309(11) -0.0096(9) 0.0021(9) -0.0051(9) C28 0.0359(12) 0.0343(12) 0.0324(12) -0.0125(10) 0.0020(10) -0.0085(10) C29 0.0423(14) 0.0365(13) 0.0432(14) -0.0122(11) 0.0068(11) -0.0162(11) C30 0.0506(15) 0.0341(13) 0.0418(13) -0.0146(11) 0.0067(11) -0.0175(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O1 2.2615(15) . ? Cd1 N4 2.300(2) 1_644 ? Cd1 O2 2.3062(17) 2_755 ? Cd1 N1 2.315(2) . ? Cd1 O3 2.3641(15) 1_545 ? Cd1 O4 2.4291(17) 1_545 ? Cd1 C8 2.726(2) 1_545 ? S1 C20 1.729(2) . ? S1 C23 1.731(2) . ? S2 C27 1.717(2) . ? S2 C24 1.733(2) . ? O1 C1 1.261(3) . ? O2 C1 1.245(3) . ? O2 Cd1 2.3062(17) 2_755 ? O3 C8 1.254(3) . ? O3 Cd1 2.3642(15) 1_565 ? O4 C8 1.250(2) . ? O4 Cd1 2.4291(17) 1_565 ? N1 C17 1.309(3) . ? N1 C18 1.368(3) . ? N2 C17 1.352(3) . ? N2 C19 1.382(3) . ? N2 C20 1.410(3) . ? N3 C28 1.362(3) . ? N3 C29 1.379(3) . ? N3 C27 1.420(3) . ? N4 C28 1.313(3) . ? N4 C30 1.378(3) . ? N4 Cd1 2.300(2) 1_466 ? C1 C2 1.510(3) . ? C2 C7 1.396(3) . ? C2 C3 1.399(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.396(3) . ? C4 C8 1.511(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.387(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 Cd1 2.726(2) 1_565 ? C17 H17 0.9300 . ? C18 C19 1.350(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.342(3) . ? C21 C22 1.413(3) . ? C21 H21 0.9300 . ? C22 C23 1.363(3) . ? C22 H22 0.9300 . ? C23 C24 1.450(3) . ? C24 C25 1.355(3) . ? C25 C26 1.420(3) . ? C25 H25 0.9300 . ? C26 C27 1.348(3) . ? C26 H26 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.349(3) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 N4 96.74(7) . 1_644 ? O1 Cd1 O2 111.58(6) . 2_755 ? N4 Cd1 O2 90.32(7) 1_644 2_755 ? O1 Cd1 N1 85.95(7) . . ? N4 Cd1 N1 169.71(7) 1_644 . ? O2 Cd1 N1 79.47(7) 2_755 . ? O1 Cd1 O3 146.26(6) . 1_545 ? N4 Cd1 O3 84.90(7) 1_644 1_545 ? O2 Cd1 O3 102.09(6) 2_755 1_545 ? N1 Cd1 O3 98.40(7) . 1_545 ? O1 Cd1 O4 92.20(6) . 1_545 ? N4 Cd1 O4 100.12(7) 1_644 1_545 ? O2 Cd1 O4 152.80(6) 2_755 1_545 ? N1 Cd1 O4 89.68(7) . 1_545 ? O3 Cd1 O4 54.60(5) 1_545 1_545 ? O1 Cd1 C8 119.13(6) . 1_545 ? N4 Cd1 C8 91.71(7) 1_644 1_545 ? O2 Cd1 C8 128.59(6) 2_755 1_545 ? N1 Cd1 C8 95.67(7) . 1_545 ? O3 Cd1 C8 27.35(6) 1_545 1_545 ? O4 Cd1 C8 27.29(6) 1_545 1_545 ? C20 S1 C23 91.29(11) . . ? C27 S2 C24 91.19(11) . . ? C1 O1 Cd1 120.40(15) . . ? C1 O2 Cd1 142.05(17) . 2_755 ? C8 O3 Cd1 92.61(12) . 1_565 ? C8 O4 Cd1 89.70(13) . 1_565 ? C17 N1 C18 105.6(2) . . ? C17 N1 Cd1 123.14(17) . . ? C18 N1 Cd1 131.04(16) . . ? C17 N2 C19 106.6(2) . . ? C17 N2 C20 126.5(2) . . ? C19 N2 C20 126.8(2) . . ? C28 N3 C29 106.78(19) . . ? C28 N3 C27 126.98(19) . . ? C29 N3 C27 126.0(2) . . ? C28 N4 C30 106.4(2) . . ? C28 N4 Cd1 126.63(17) . 1_466 ? C30 N4 Cd1 126.94(16) . 1_466 ? O2 C1 O1 125.1(2) . . ? O2 C1 C2 118.71(19) . . ? O1 C1 C2 116.15(19) . . ? C7 C2 C3 118.89(18) . . ? C7 C2 C1 119.52(19) . . ? C3 C2 C1 121.48(18) . . ? C4 C3 C2 120.40(19) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.71(19) . . ? C3 C4 C8 120.23(19) . . ? C5 C4 C8 120.02(18) . . ? C6 C5 C4 120.55(19) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C2 121.10(19) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? O4 C8 O3 122.89(19) . . ? O4 C8 C4 118.76(19) . . ? O3 C8 C4 118.35(18) . . ? O4 C8 Cd1 63.01(11) . 1_565 ? O3 C8 Cd1 60.04(11) . 1_565 ? C4 C8 Cd1 175.88(15) . 1_565 ? N1 C17 N2 111.7(2) . . ? N1 C17 H17 124.2 . . ? N2 C17 H17 124.2 . . ? C19 C18 N1 110.5(2) . . ? C19 C18 H18 124.8 . . ? N1 C18 H18 124.8 . . ? C18 C19 N2 105.6(2) . . ? C18 C19 H19 127.2 . . ? N2 C19 H19 127.2 . . ? C21 C20 N2 128.2(2) . . ? C21 C20 S1 112.03(18) . . ? N2 C20 S1 119.78(17) . . ? C20 C21 C22 112.6(2) . . ? C20 C21 H21 123.7 . . ? C22 C21 H21 123.7 . . ? C23 C22 C21 113.6(2) . . ? C23 C22 H22 123.2 . . ? C21 C22 H22 123.2 . . ? C22 C23 C24 129.4(2) . . ? C22 C23 S1 110.52(17) . . ? C24 C23 S1 120.05(18) . . ? C25 C24 C23 130.8(2) . . ? C25 C24 S2 110.80(18) . . ? C23 C24 S2 118.40(18) . . ? C24 C25 C26 113.5(2) . . ? C24 C25 H25 123.2 . . ? C26 C25 H25 123.2 . . ? C27 C26 C25 112.0(2) . . ? C27 C26 H26 124.0 . . ? C25 C26 H26 124.0 . . ? C26 C27 N3 127.5(2) . . ? C26 C27 S2 112.52(18) . . ? N3 C27 S2 119.97(17) . . ? N4 C28 N3 110.8(2) . . ? N4 C28 H28 124.6 . . ? N3 C28 H28 124.6 . . ? C30 C29 N3 106.5(2) . . ? C30 C29 H29 126.8 . . ? N3 C29 H29 126.8 . . ? C29 C30 N4 109.6(2) . . ? C29 C30 H30 125.2 . . ? N4 C30 H30 125.2 . . ? 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 N4 Cd1 O1 C1 76.81(18) 1_644 . . . ? O2 Cd1 O1 C1 -16.2(2) 2_755 . . . ? N1 Cd1 O1 C1 -93.20(18) . . . . ? O3 Cd1 O1 C1 167.72(15) 1_545 . . . ? O4 Cd1 O1 C1 177.28(18) 1_545 . . . ? C8 Cd1 O1 C1 172.56(16) 1_545 . . . ? O1 Cd1 N1 C17 -7.7(2) . . . . ? N4 Cd1 N1 C17 -113.2(4) 1_644 . . . ? O2 Cd1 N1 C17 -120.5(2) 2_755 . . . ? O3 Cd1 N1 C17 138.7(2) 1_545 . . . ? O4 Cd1 N1 C17 84.6(2) 1_545 . . . ? C8 Cd1 N1 C17 111.2(2) 1_545 . . . ? O1 Cd1 N1 C18 165.8(2) . . . . ? N4 Cd1 N1 C18 60.2(5) 1_644 . . . ? O2 Cd1 N1 C18 53.0(2) 2_755 . . . ? O3 Cd1 N1 C18 -47.9(2) 1_545 . . . ? O4 Cd1 N1 C18 -102.0(2) 1_545 . . . ? C8 Cd1 N1 C18 -75.3(2) 1_545 . . . ? Cd1 O2 C1 O1 105.0(3) 2_755 . . . ? Cd1 O2 C1 C2 -74.2(3) 2_755 . . . ? Cd1 O1 C1 O2 -28.4(3) . . . . ? Cd1 O1 C1 C2 150.84(15) . . . . ? O2 C1 C2 C7 -176.9(2) . . . . ? O1 C1 C2 C7 3.9(3) . . . . ? O2 C1 C2 C3 7.2(3) . . . . ? O1 C1 C2 C3 -172.1(2) . . . . ? C7 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C4 175.1(2) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C2 C3 C4 C8 -177.49(19) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C8 C4 C5 C6 178.3(2) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C3 C2 C7 C6 0.9(3) . . . . ? C1 C2 C7 C6 -175.2(2) . . . . ? Cd1 O4 C8 O3 -4.6(2) 1_565 . . . ? Cd1 O4 C8 C4 175.79(17) 1_565 . . . ? Cd1 O3 C8 O4 4.7(2) 1_565 . . . ? Cd1 O3 C8 C4 -175.66(16) 1_565 . . . ? C3 C4 C8 O4 -155.4(2) . . . . ? C5 C4 C8 O4 26.9(3) . . . . ? C3 C4 C8 O3 25.0(3) . . . . ? C5 C4 C8 O3 -152.7(2) . . . . ? C18 N1 C17 N2 0.3(3) . . . . ? Cd1 N1 C17 N2 175.17(15) . . . . ? C19 N2 C17 N1 0.1(3) . . . . ? C20 N2 C17 N1 -178.5(2) . . . . ? C17 N1 C18 C19 -0.5(3) . . . . ? Cd1 N1 C18 C19 -174.87(18) . . . . ? N1 C18 C19 N2 0.6(3) . . . . ? C17 N2 C19 C18 -0.4(3) . . . . ? C20 N2 C19 C18 178.1(2) . . . . ? C17 N2 C20 C21 177.9(3) . . . . ? C19 N2 C20 C21 -0.3(4) . . . . ? C17 N2 C20 S1 -2.1(3) . . . . ? C19 N2 C20 S1 179.7(2) . . . . ? C23 S1 C20 C21 0.1(2) . . . . ? C23 S1 C20 N2 -180.0(2) . . . . ? N2 C20 C21 C22 179.6(3) . . . . ? S1 C20 C21 C22 -0.4(3) . . . . ? C20 C21 C22 C23 0.7(4) . . . . ? C21 C22 C23 C24 179.8(2) . . . . ? C21 C22 C23 S1 -0.6(3) . . . . ? C20 S1 C23 C22 0.3(2) . . . . ? C20 S1 C23 C24 179.98(19) . . . . ? C22 C23 C24 C25 -173.5(3) . . . . ? S1 C23 C24 C25 6.9(4) . . . . ? C22 C23 C24 S2 7.1(4) . . . . ? S1 C23 C24 S2 -172.47(14) . . . . ? C27 S2 C24 C25 0.2(2) . . . . ? C27 S2 C24 C23 179.71(19) . . . . ? C23 C24 C25 C26 -179.6(2) . . . . ? S2 C24 C25 C26 -0.2(3) . . . . ? C24 C25 C26 C27 0.1(4) . . . . ? C25 C26 C27 N3 -178.0(2) . . . . ? C25 C26 C27 S2 0.1(3) . . . . ? C28 N3 C27 C26 -159.8(3) . . . . ? C29 N3 C27 C26 25.9(4) . . . . ? C28 N3 C27 S2 22.2(3) . . . . ? C29 N3 C27 S2 -152.1(2) . . . . ? C24 S2 C27 C26 -0.2(2) . . . . ? C24 S2 C27 N3 178.1(2) . . . . ? C30 N4 C28 N3 -0.4(3) . . . . ? Cd1 N4 C28 N3 177.39(15) 1_466 . . . ? C29 N3 C28 N4 0.7(3) . . . . ? C27 N3 C28 N4 -174.4(2) . . . . ? C28 N3 C29 C30 -0.8(3) . . . . ? C27 N3 C29 C30 174.4(2) . . . . ? N3 C29 C30 N4 0.5(3) . . . . ? C28 N4 C30 C29 -0.1(3) . . . . ? Cd1 N4 C30 C29 -177.88(18) 1_466 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.728 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 963195' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 N4 O5 S2 Zn' _chemical_formula_sum 'C22 H14 N4 O5 S2 Zn' _chemical_formula_weight 543.86 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4003(6) _cell_length_b 9.8766(7) _cell_length_c 12.0339(8) _cell_angle_alpha 82.4750(10) _cell_angle_beta 80.7070(10) _cell_angle_gamma 72.3670(10) _cell_volume 1046.79(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4612 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.43 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7006 _exptl_absorpt_correction_T_max 0.8153 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6916 _diffrn_reflns_av_R_equivalents 0.0090 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4569 _reflns_number_gt 4134 _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^)+(0.0600P)^2^+0.1200P] 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 4569 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.58968(17) 0.06789(16) 0.64184(13) 0.0262(3) Uani 1 1 d . . . C2 C 0.57757(17) 0.16875(16) 0.72916(12) 0.0240(3) Uani 1 1 d . . . C3 C 0.56743(17) 0.31121(16) 0.69600(12) 0.0249(3) Uani 1 1 d . . . H3 H 0.5807 0.3421 0.6197 0.030 Uiso 1 1 calc R . . C4 C 0.53717(16) 0.40769(16) 0.77788(13) 0.0234(3) Uani 1 1 d . . . C5 C 0.51974(18) 0.56386(17) 0.74593(14) 0.0283(3) Uani 1 1 d . . . C6 C 0.52086(17) 0.35956(16) 0.89172(13) 0.0259(3) Uani 1 1 d . . . H6 H 0.4990 0.4240 0.9462 0.031 Uiso 1 1 calc R . . C7 C 0.53685(18) 0.21653(17) 0.92489(13) 0.0265(3) Uani 1 1 d . . . C8 C 0.56382(18) 0.12066(16) 0.84350(13) 0.0259(3) Uani 1 1 d . . . H8 H 0.5726 0.0249 0.8653 0.031 Uiso 1 1 calc R . . C9 C 0.2504(2) 0.3665(2) 0.56928(15) 0.0373(4) Uani 1 1 d . . . H9 H 0.3147 0.4204 0.5738 0.045 Uiso 1 1 calc R . . C10 C 0.1588(2) 0.2103(2) 0.52295(16) 0.0420(4) Uani 1 1 d . . . H10 H 0.1498 0.1348 0.4885 0.050 Uiso 1 1 calc R . . C11 C 0.0513(2) 0.2882(2) 0.59716(16) 0.0430(4) Uani 1 1 d . . . H11 H -0.0434 0.2767 0.6229 0.052 Uiso 1 1 calc R . . C12 C 0.0407(2) 0.48884(19) 0.70728(15) 0.0343(4) Uani 1 1 d . . . C13 C -0.1047(2) 0.5671(2) 0.72286(17) 0.0431(4) Uani 1 1 d . . . H13 H -0.1766 0.5642 0.6791 0.052 Uiso 1 1 calc R . . C14 C -0.1353(2) 0.6539(2) 0.81333(17) 0.0416(4) Uani 1 1 d . . . H14 H -0.2300 0.7148 0.8351 0.050 Uiso 1 1 calc R . . C15 C -0.01231(19) 0.63999(19) 0.86585(15) 0.0323(4) Uani 1 1 d . . . C16 C 0.00146(19) 0.71235(19) 0.95854(14) 0.0331(4) Uani 1 1 d . . . C17 C 0.1234(2) 0.6966(2) 1.01156(19) 0.0485(5) Uani 1 1 d . . . H17 H 0.2172 0.6332 0.9912 0.058 Uiso 1 1 calc R . . C18 C 0.0949(2) 0.7856(2) 1.10051(18) 0.0475(5) Uani 1 1 d . . . H18 H 0.1664 0.7859 1.1455 0.057 Uiso 1 1 calc R . . C19 C -0.0480(2) 0.86973(19) 1.11232(14) 0.0328(4) Uani 1 1 d . . . C20 C -0.2645(2) 1.01290(19) 1.23103(14) 0.0331(4) Uani 1 1 d . . . H20 H -0.3375 0.9837 1.2050 0.040 Uiso 1 1 calc R . . C21 C -0.0457(2) 1.0350(2) 1.25215(16) 0.0414(4) Uani 1 1 d . . . H21 H 0.0568 1.0258 1.2446 0.050 Uiso 1 1 calc R . . C22 C -0.1552(2) 1.1154(2) 1.32327(16) 0.0409(4) Uani 1 1 d . . . H22 H -0.1402 1.1716 1.3740 0.049 Uiso 1 1 calc R . . N1 N 0.28367(18) 0.25920(16) 0.50590(13) 0.0360(3) Uani 1 1 d . . . N2 N 0.11051(17) 0.38823(16) 0.62691(13) 0.0353(3) Uani 1 1 d . . . N3 N -0.11619(17) 0.96949(16) 1.19295(12) 0.0326(3) Uani 1 1 d . . . N4 N -0.29275(17) 1.10148(16) 1.30944(12) 0.0338(3) Uani 1 1 d . . . O1 O 0.60061(15) 0.11424(14) 0.54033(9) 0.0381(3) Uani 1 1 d . . . O2 O 0.58650(15) -0.05747(12) 0.67744(10) 0.0356(3) Uani 1 1 d . . . O3 O 0.51697(16) 0.60722(12) 0.64232(10) 0.0417(3) Uani 1 1 d . . . O4 O 0.51098(19) 0.64115(14) 0.82116(12) 0.0505(4) Uani 1 1 d . . . O5 O 0.52664(17) 0.16415(13) 1.03549(9) 0.0411(3) Uani 1 1 d . . . H5 H 0.5179 0.2279 1.0757 0.062 Uiso 1 1 calc R . . S1 S 0.14406(5) 0.51672(5) 0.80388(4) 0.03953(12) Uani 1 1 d . . . S2 S -0.15235(5) 0.84285(5) 1.01575(4) 0.03813(12) Uani 1 1 d . . . Zn1 Zn 0.49259(2) 0.186024(17) 0.399935(14) 0.02642(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0322(8) 0.0231(7) 0.0224(7) -0.0072(6) -0.0010(6) -0.0057(6) C2 0.0308(7) 0.0199(7) 0.0211(7) -0.0048(5) -0.0012(6) -0.0070(6) C3 0.0314(8) 0.0212(7) 0.0203(7) -0.0011(5) 0.0001(6) -0.0070(6) C4 0.0264(7) 0.0175(7) 0.0267(7) -0.0031(6) -0.0020(6) -0.0072(5) C5 0.0308(8) 0.0192(7) 0.0333(8) -0.0035(6) -0.0007(6) -0.0060(6) C6 0.0338(8) 0.0211(7) 0.0243(7) -0.0075(6) -0.0027(6) -0.0082(6) C7 0.0376(8) 0.0239(8) 0.0201(7) -0.0024(6) -0.0033(6) -0.0122(6) C8 0.0390(8) 0.0181(7) 0.0221(7) -0.0024(5) -0.0038(6) -0.0103(6) C9 0.0365(9) 0.0378(10) 0.0364(9) -0.0160(8) 0.0018(7) -0.0072(7) C10 0.0549(11) 0.0338(10) 0.0391(10) -0.0137(8) 0.0052(8) -0.0168(8) C11 0.0458(10) 0.0425(11) 0.0423(11) -0.0124(8) 0.0070(8) -0.0182(8) C12 0.0367(9) 0.0333(9) 0.0297(8) -0.0107(7) 0.0013(7) -0.0048(7) C13 0.0356(9) 0.0493(12) 0.0412(10) -0.0149(9) -0.0053(8) -0.0028(8) C14 0.0312(9) 0.0440(11) 0.0441(10) -0.0185(9) 0.0004(7) 0.0008(8) C15 0.0305(8) 0.0301(8) 0.0316(8) -0.0102(7) 0.0046(6) -0.0028(6) C16 0.0302(8) 0.0319(9) 0.0323(9) -0.0121(7) 0.0059(6) -0.0027(7) C17 0.0309(9) 0.0561(13) 0.0542(12) -0.0310(10) -0.0002(8) 0.0021(8) C18 0.0324(9) 0.0595(13) 0.0498(12) -0.0256(10) -0.0039(8) -0.0042(9) C19 0.0355(9) 0.0329(9) 0.0273(8) -0.0096(7) 0.0041(6) -0.0073(7) C20 0.0360(9) 0.0325(9) 0.0259(8) -0.0088(7) -0.0010(6) -0.0013(7) C21 0.0445(10) 0.0437(11) 0.0402(10) -0.0141(8) 0.0028(8) -0.0189(8) C22 0.0541(11) 0.0359(10) 0.0351(9) -0.0112(8) 0.0015(8) -0.0170(8) N1 0.0433(8) 0.0313(8) 0.0305(7) -0.0104(6) 0.0018(6) -0.0065(6) N2 0.0382(8) 0.0340(8) 0.0320(8) -0.0134(6) 0.0016(6) -0.0067(6) N3 0.0377(8) 0.0300(7) 0.0271(7) -0.0081(6) 0.0019(6) -0.0063(6) N4 0.0440(8) 0.0290(7) 0.0240(7) -0.0060(6) -0.0012(6) -0.0040(6) O1 0.0550(8) 0.0379(7) 0.0197(6) -0.0049(5) -0.0041(5) -0.0100(6) O2 0.0566(8) 0.0228(6) 0.0293(6) -0.0105(5) 0.0001(5) -0.0137(5) O3 0.0662(9) 0.0182(6) 0.0299(6) 0.0001(5) 0.0085(6) -0.0046(5) O4 0.0833(10) 0.0238(7) 0.0499(8) -0.0098(6) -0.0232(7) -0.0133(7) O5 0.0807(10) 0.0289(6) 0.0176(5) -0.0021(5) -0.0051(6) -0.0221(6) S1 0.0302(2) 0.0435(3) 0.0405(3) -0.0214(2) -0.00145(18) 0.00157(18) S2 0.0335(2) 0.0401(3) 0.0352(2) -0.01742(19) -0.00180(17) 0.00211(18) Zn1 0.04152(13) 0.01631(11) 0.01887(11) -0.00507(7) -0.00017(8) -0.00499(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2466(19) . ? C1 O2 1.2636(19) . ? C1 C2 1.509(2) . ? C2 C3 1.390(2) . ? C2 C8 1.394(2) . ? C3 C4 1.397(2) . ? C3 H3 0.9300 . ? C4 C6 1.390(2) . ? C4 C5 1.505(2) . ? C5 O4 1.236(2) . ? C5 O3 1.266(2) . ? C6 C7 1.386(2) . ? C6 H6 0.9300 . ? C7 O5 1.3626(18) . ? C7 C8 1.392(2) . ? C8 H8 0.9300 . ? C9 N1 1.318(2) . ? C9 N2 1.352(2) . ? C9 H9 0.9300 . ? C10 C11 1.352(3) . ? C10 N1 1.376(2) . ? C10 H10 0.9300 . ? C11 N2 1.380(2) . ? C11 H11 0.9300 . ? C12 C13 1.348(3) . ? C12 N2 1.416(2) . ? C12 S1 1.7266(18) . ? C13 C14 1.414(3) . ? C13 H13 0.9300 . ? C14 C15 1.368(3) . ? C14 H14 0.9300 . ? C15 C16 1.443(3) . ? C15 S1 1.7317(17) . ? C16 C17 1.360(3) . ? C16 S2 1.7343(17) . ? C17 C18 1.414(3) . ? C17 H17 0.9300 . ? C18 C19 1.345(3) . ? C18 H18 0.9300 . ? C19 N3 1.411(2) . ? C19 S2 1.7289(18) . ? C20 N4 1.312(2) . ? C20 N3 1.349(2) . ? C20 H20 0.9300 . ? C21 C22 1.349(3) . ? C21 N3 1.378(2) . ? C21 H21 0.9300 . ? C22 N4 1.379(3) . ? C22 H22 0.9300 . ? N1 Zn1 2.1397(15) . ? N4 Zn1 2.1124(15) 1_466 ? O1 Zn1 2.0475(12) . ? O2 Zn1 2.0339(12) 2_656 ? O3 Zn1 2.0170(12) 2_666 ? O5 H5 0.8200 . ? Zn1 O3 2.0170(12) 2_666 ? Zn1 O2 2.0339(12) 2_656 ? Zn1 N4 2.1124(15) 1_644 ? 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 C1 O2 124.80(14) . . ? O1 C1 C2 117.92(14) . . ? O2 C1 C2 117.27(13) . . ? C3 C2 C8 120.41(13) . . ? C3 C2 C1 120.00(13) . . ? C8 C2 C1 119.37(13) . . ? C2 C3 C4 119.66(13) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C6 C4 C3 119.62(14) . . ? C6 C4 C5 118.83(14) . . ? C3 C4 C5 121.55(14) . . ? O4 C5 O3 124.11(16) . . ? O4 C5 C4 118.66(15) . . ? O3 C5 C4 117.23(14) . . ? C7 C6 C4 120.73(14) . . ? C7 C6 H6 119.6 . . ? C4 C6 H6 119.6 . . ? O5 C7 C6 122.62(14) . . ? O5 C7 C8 117.62(14) . . ? C6 C7 C8 119.76(14) . . ? C7 C8 C2 119.75(14) . . ? C7 C8 H8 120.1 . . ? C2 C8 H8 120.1 . . ? N1 C9 N2 111.24(16) . . ? N1 C9 H9 124.4 . . ? N2 C9 H9 124.4 . . ? C11 C10 N1 109.91(17) . . ? C11 C10 H10 125.0 . . ? N1 C10 H10 125.0 . . ? C10 C11 N2 106.12(17) . . ? C10 C11 H11 126.9 . . ? N2 C11 H11 126.9 . . ? C13 C12 N2 127.80(17) . . ? C13 C12 S1 112.39(14) . . ? N2 C12 S1 119.76(13) . . ? C12 C13 C14 112.20(17) . . ? C12 C13 H13 123.9 . . ? C14 C13 H13 123.9 . . ? C15 C14 C13 113.64(16) . . ? C15 C14 H14 123.2 . . ? C13 C14 H14 123.2 . . ? C14 C15 C16 129.71(16) . . ? C14 C15 S1 110.54(13) . . ? C16 C15 S1 119.73(14) . . ? C17 C16 C15 129.51(17) . . ? C17 C16 S2 110.63(14) . . ? C15 C16 S2 119.85(14) . . ? C16 C17 C18 113.89(17) . . ? C16 C17 H17 123.1 . . ? C18 C17 H17 123.1 . . ? C19 C18 C17 111.99(17) . . ? C19 C18 H18 124.0 . . ? C17 C18 H18 124.0 . . ? C18 C19 N3 127.46(17) . . ? C18 C19 S2 112.53(14) . . ? N3 C19 S2 120.00(13) . . ? N4 C20 N3 111.43(16) . . ? N4 C20 H20 124.3 . . ? N3 C20 H20 124.3 . . ? C22 C21 N3 106.18(17) . . ? C22 C21 H21 126.9 . . ? N3 C21 H21 126.9 . . ? C21 C22 N4 109.74(17) . . ? C21 C22 H22 125.1 . . ? N4 C22 H22 125.1 . . ? C9 N1 C10 105.82(15) . . ? C9 N1 Zn1 124.49(13) . . ? C10 N1 Zn1 129.68(12) . . ? C9 N2 C11 106.91(15) . . ? C9 N2 C12 126.77(15) . . ? C11 N2 C12 126.23(16) . . ? C20 N3 C21 106.88(15) . . ? C20 N3 C19 125.62(15) . . ? C21 N3 C19 127.41(16) . . ? C20 N4 C22 105.76(15) . . ? C20 N4 Zn1 124.40(13) . 1_466 ? C22 N4 Zn1 129.67(12) . 1_466 ? C1 O1 Zn1 146.28(12) . . ? C1 O2 Zn1 126.22(11) . 2_656 ? C5 O3 Zn1 116.55(11) . 2_666 ? C7 O5 H5 109.5 . . ? C12 S1 C15 91.22(8) . . ? C19 S2 C16 90.93(9) . . ? O3 Zn1 O2 128.75(5) 2_666 2_656 ? O3 Zn1 O1 109.22(5) 2_666 . ? O2 Zn1 O1 122.03(5) 2_656 . ? O3 Zn1 N4 96.02(6) 2_666 1_644 ? O2 Zn1 N4 88.72(6) 2_656 1_644 ? O1 Zn1 N4 84.70(5) . 1_644 ? O3 Zn1 N1 87.28(6) 2_666 . ? O2 Zn1 N1 92.77(6) 2_656 . ? O1 Zn1 N1 89.91(6) . . ? N4 Zn1 N1 174.37(5) 1_644 . ? 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 C1 C2 C3 4.8(2) . . . . ? O2 C1 C2 C3 -174.51(14) . . . . ? O1 C1 C2 C8 179.43(14) . . . . ? O2 C1 C2 C8 0.1(2) . . . . ? C8 C2 C3 C4 -2.6(2) . . . . ? C1 C2 C3 C4 171.92(14) . . . . ? C2 C3 C4 C6 1.4(2) . . . . ? C2 C3 C4 C5 -177.80(14) . . . . ? C6 C4 C5 O4 9.3(2) . . . . ? C3 C4 C5 O4 -171.48(15) . . . . ? C6 C4 C5 O3 -171.62(14) . . . . ? C3 C4 C5 O3 7.6(2) . . . . ? C3 C4 C6 C7 1.1(2) . . . . ? C5 C4 C6 C7 -179.62(15) . . . . ? C4 C6 C7 O5 177.81(15) . . . . ? C4 C6 C7 C8 -2.5(2) . . . . ? O5 C7 C8 C2 -178.99(15) . . . . ? C6 C7 C8 C2 1.3(2) . . . . ? C3 C2 C8 C7 1.3(2) . . . . ? C1 C2 C8 C7 -173.32(14) . . . . ? N1 C10 C11 N2 0.1(2) . . . . ? N2 C12 C13 C14 178.38(19) . . . . ? S1 C12 C13 C14 0.9(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 178.4(2) . . . . ? C13 C14 C15 S1 -0.5(2) . . . . ? C14 C15 C16 C17 178.9(2) . . . . ? S1 C15 C16 C17 -2.2(3) . . . . ? C14 C15 C16 S2 -2.4(3) . . . . ? S1 C15 C16 S2 176.49(9) . . . . ? C15 C16 C17 C18 -179.5(2) . . . . ? S2 C16 C17 C18 1.6(3) . . . . ? C16 C17 C18 C19 -1.2(3) . . . . ? C17 C18 C19 N3 178.93(18) . . . . ? C17 C18 C19 S2 0.2(3) . . . . ? N3 C21 C22 N4 -0.1(2) . . . . ? N2 C9 N1 C10 0.5(2) . . . . ? N2 C9 N1 Zn1 179.98(11) . . . . ? C11 C10 N1 C9 -0.3(2) . . . . ? C11 C10 N1 Zn1 -179.82(14) . . . . ? N1 C9 N2 C11 -0.4(2) . . . . ? N1 C9 N2 C12 176.36(17) . . . . ? C10 C11 N2 C9 0.2(2) . . . . ? C10 C11 N2 C12 -176.62(18) . . . . ? C13 C12 N2 C9 142.1(2) . . . . ? S1 C12 N2 C9 -40.6(3) . . . . ? C13 C12 N2 C11 -41.7(3) . . . . ? S1 C12 N2 C11 135.55(18) . . . . ? N4 C20 N3 C21 0.3(2) . . . . ? N4 C20 N3 C19 177.13(16) . . . . ? C22 C21 N3 C20 -0.1(2) . . . . ? C22 C21 N3 C19 -176.85(17) . . . . ? C18 C19 N3 C20 -154.0(2) . . . . ? S2 C19 N3 C20 24.6(2) . . . . ? C18 C19 N3 C21 22.1(3) . . . . ? S2 C19 N3 C21 -159.19(16) . . . . ? N3 C20 N4 C22 -0.4(2) . . . . ? N3 C20 N4 Zn1 -175.98(11) . . . 1_466 ? C21 C22 N4 C20 0.3(2) . . . . ? C21 C22 N4 Zn1 175.59(13) . . . 1_466 ? O2 C1 O1 Zn1 76.1(3) . . . . ? C2 C1 O1 Zn1 -103.2(2) . . . . ? O1 C1 O2 Zn1 -28.9(2) . . . 2_656 ? C2 C1 O2 Zn1 150.41(11) . . . 2_656 ? O4 C5 O3 Zn1 3.0(2) . . . 2_666 ? C4 C5 O3 Zn1 -176.07(10) . . . 2_666 ? C13 C12 S1 C15 -1.03(17) . . . . ? N2 C12 S1 C15 -178.70(15) . . . . ? C14 C15 S1 C12 0.84(16) . . . . ? C16 C15 S1 C12 -178.21(16) . . . . ? C18 C19 S2 C16 0.63(18) . . . . ? N3 C19 S2 C16 -178.23(15) . . . . ? C17 C16 S2 C19 -1.29(17) . . . . ? C15 C16 S2 C19 179.77(16) . . . . ? C1 O1 Zn1 O3 115.2(2) . . . 2_666 ? C1 O1 Zn1 O2 -65.1(2) . . . 2_656 ? C1 O1 Zn1 N4 -150.2(2) . . . 1_644 ? C1 O1 Zn1 N1 28.1(2) . . . . ? C9 N1 Zn1 O3 -40.70(16) . . . 2_666 ? C10 N1 Zn1 O3 138.69(17) . . . 2_666 ? C9 N1 Zn1 O2 -169.39(15) . . . 2_656 ? C10 N1 Zn1 O2 10.00(17) . . . 2_656 ? C9 N1 Zn1 O1 68.55(16) . . . . ? C10 N1 Zn1 O1 -112.06(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O4 0.82 1.84 2.6568(18) 173.6 2_667 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.352 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 963196' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N4 O4 S2 Zn' _chemical_formula_sum 'C24 H24 N4 O4 S2 Zn' _chemical_formula_weight 561.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4879(10) _cell_length_b 20.6148(19) _cell_length_c 15.5100(11) _cell_angle_alpha 90.00 _cell_angle_beta 121.819(5) _cell_angle_gamma 90.00 _cell_volume 2849.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1573 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 18.93 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7590 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17968 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.10 _reflns_number_total 6271 _reflns_number_gt 3850 _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^)+(0.0566P)^2^+0.1000P] 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 6271 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 -0.27599(5) 0.78935(2) 0.22411(3) 0.03571(14) Uani 1 1 d . . . S1 S 0.29925(12) 0.94090(5) 0.44474(9) 0.0465(3) Uani 1 1 d . . . S2 S -0.03866(12) 0.58338(5) 0.06995(9) 0.0477(3) Uani 1 1 d . . . O1 O -0.1265(3) 0.76406(14) 0.3643(2) 0.0462(7) Uani 1 1 d . . . O2 O -0.1791(3) 0.66037(15) 0.3217(2) 0.0550(8) Uani 1 1 d . . . O3 O 0.4971(3) 0.63786(14) 0.6073(3) 0.0623(9) Uani 1 1 d . . . O4 O 0.5218(3) 0.71408(12) 0.70476(19) 0.0380(6) Uani 1 1 d . . . N1 N -0.1624(4) 0.86974(16) 0.2241(3) 0.0453(8) Uani 1 1 d . . . N2 N 0.0232(4) 0.93735(15) 0.2687(3) 0.0430(8) Uani 1 1 d . . . N3 N -0.2995(4) 0.73902(16) 0.1039(3) 0.0464(9) Uani 1 1 d . . . N4 N -0.2650(4) 0.66580(16) 0.0152(3) 0.0440(8) Uani 1 1 d . . . C1 C -0.0232(4) 0.88214(19) 0.2901(3) 0.0414(10) Uani 1 1 d . . . H1 H 0.0378 0.8560 0.3458 0.050 Uiso 1 1 calc R . . C2 C -0.2168(5) 0.9221(2) 0.1622(3) 0.0517(11) Uani 1 1 d . . . H2 H -0.3152 0.9275 0.1086 0.062 Uiso 1 1 calc R . . C3 C -0.1027(5) 0.9656(2) 0.1919(3) 0.0508(11) Uani 1 1 d . . . H3 H -0.1099 1.0066 0.1647 0.061 Uiso 1 1 calc R . . C4 C 0.1716(4) 0.96668(18) 0.3234(3) 0.0380(9) Uani 1 1 d . . . C5 C 0.2245(5) 1.0122(2) 0.2896(4) 0.0528(11) Uani 1 1 d . . . H5 H 0.1725 1.0289 0.2241 0.063 Uiso 1 1 calc R . . C6 C 0.3694(5) 1.03179(19) 0.3661(3) 0.0476(11) Uani 1 1 d . . . H6 H 0.4208 1.0650 0.3567 0.057 Uiso 1 1 calc R . . C7 C 0.4290(4) 0.99825(17) 0.4555(3) 0.0402(9) Uani 1 1 d . . . C8 C -0.2327(4) 0.6836(2) 0.1068(3) 0.0396(9) Uani 1 1 d . . . H8 H -0.1710 0.6602 0.1658 0.048 Uiso 1 1 calc R . . C9 C -0.3771(4) 0.7585(2) 0.0063(3) 0.0432(10) Uani 1 1 d . . . H9 H -0.4334 0.7964 -0.0162 0.052 Uiso 1 1 calc R . . C10 C -0.3632(5) 0.7163(2) -0.0548(3) 0.0484(10) Uani 1 1 d . . . H10 H -0.4058 0.7187 -0.1246 0.058 Uiso 1 1 calc R . . C11 C -0.2145(4) 0.61043(19) -0.0121(3) 0.0432(10) Uani 1 1 d . . . C12 C -0.2859(5) 0.5781(2) -0.1014(4) 0.0490(11) Uani 1 1 d . . . H12 H -0.3817 0.5886 -0.1549 0.059 Uiso 1 1 calc R . . C13 C -0.2019(6) 0.5282(2) -0.1046(4) 0.0551(12) Uani 1 1 d . . . H13 H -0.2343 0.5007 -0.1599 0.066 Uiso 1 1 calc R . . C14 C -0.0636(5) 0.5238(2) -0.0160(4) 0.0511(11) Uani 1 1 d . . . C15 C -0.1043(4) 0.7033(2) 0.3822(3) 0.0440(10) Uani 1 1 d . . . C16 C 0.0177(4) 0.6858(2) 0.4914(3) 0.0478(11) Uani 1 1 d . . . C17 C 0.0395(6) 0.6128(3) 0.5093(4) 0.0710(15) Uani 1 1 d . . . H17A H -0.0284 0.5956 0.5283 0.085 Uiso 1 1 calc R . . H17B H 0.0205 0.5908 0.4483 0.085 Uiso 1 1 calc R . . C18 C 0.2017(6) 0.6031(2) 0.5949(4) 0.0696(15) Uani 1 1 d . . . H18A H 0.2512 0.5724 0.5746 0.084 Uiso 1 1 calc R . . H18B H 0.2058 0.5864 0.6547 0.084 Uiso 1 1 calc R . . C19 C 0.2797(5) 0.6696(2) 0.6177(3) 0.0509(11) Uani 1 1 d . . . H19A H 0.2658 0.6934 0.6653 0.061 Uiso 0.50 1 d PR . . C20 C 0.2161(12) 0.7109(4) 0.6697(9) 0.071(3) Uani 0.50 1 d P . . H20A H 0.2695 0.7516 0.6954 0.085 Uiso 0.50 1 d PR . . H20B H 0.2221 0.6866 0.7253 0.085 Uiso 0.50 1 d PR . . H20C H 0.1125 0.7205 0.6215 0.085 Uiso 0.50 1 d PR . . H21C H 0.1480 0.7150 0.6332 0.085 Uiso 0.50 1 d PR . . C21 C 0.0509(10) 0.7213(5) 0.5826(7) 0.061(3) Uani 0.50 1 d P . . H16A H 0.0060 0.7079 0.5421 0.073 Uiso 0.50 1 d PR . . H21A H -0.0154 0.7063 0.6044 0.073 Uiso 0.50 1 d PR . . H21B H 0.0337 0.7674 0.5685 0.073 Uiso 0.50 1 d PR . . C22 C 0.1739(5) 0.6945(3) 0.5094(4) 0.0690(15) Uani 1 1 d . . . C23 C 0.1597(7) 0.6650(3) 0.4139(4) 0.0890(18) Uani 1 1 d . . . H23A H 0.1922 0.6961 0.3834 0.133 Uiso 1 1 calc R . . H23B H 0.0569 0.6537 0.3666 0.133 Uiso 1 1 calc R . . H23C H 0.2211 0.6269 0.4320 0.133 Uiso 1 1 calc R . . C24 C 0.2166(6) 0.7656(3) 0.5046(4) 0.0842(18) Uani 1 1 d . . . H24A H 0.3155 0.7670 0.5156 0.126 Uiso 1 1 calc R . . H24B H 0.2146 0.7905 0.5562 0.126 Uiso 1 1 calc R . . H24C H 0.1461 0.7834 0.4392 0.126 Uiso 1 1 calc R . . C25 C 0.4462(5) 0.6738(2) 0.6474(4) 0.0526(11) 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 0.0283(2) 0.0385(3) 0.0349(3) 0.0045(2) 0.01294(19) -0.00178(19) S1 0.0383(6) 0.0447(6) 0.0498(7) -0.0081(5) 0.0187(5) -0.0136(5) S2 0.0470(6) 0.0464(6) 0.0486(7) 0.0055(5) 0.0244(5) 0.0116(5) O1 0.0306(15) 0.0583(18) 0.0408(16) 0.0096(14) 0.0127(13) -0.0007(13) O2 0.0513(19) 0.061(2) 0.0459(18) 0.0060(16) 0.0208(15) 0.0091(15) O3 0.058(2) 0.0488(19) 0.085(2) -0.0205(17) 0.0412(19) -0.0172(15) O4 0.0320(14) 0.0424(15) 0.0340(14) 0.0045(13) 0.0136(12) -0.0045(12) N1 0.037(2) 0.046(2) 0.054(2) 0.0045(17) 0.0250(18) -0.0009(15) N2 0.0384(19) 0.0385(19) 0.045(2) 0.0089(15) 0.0173(16) 0.0056(14) N3 0.053(2) 0.045(2) 0.047(2) -0.0009(16) 0.0301(18) -0.0067(17) N4 0.042(2) 0.048(2) 0.046(2) 0.0032(16) 0.0258(17) -0.0057(15) C1 0.038(2) 0.049(3) 0.036(2) -0.0057(18) 0.0181(19) -0.0010(18) C2 0.045(3) 0.050(3) 0.046(3) -0.001(2) 0.015(2) 0.004(2) C3 0.049(3) 0.039(2) 0.054(3) 0.006(2) 0.020(2) 0.0015(19) C4 0.037(2) 0.033(2) 0.047(2) -0.0034(17) 0.0240(19) 0.0011(16) C5 0.045(3) 0.068(3) 0.045(3) -0.011(2) 0.024(2) -0.017(2) C6 0.049(3) 0.037(2) 0.054(3) -0.0018(19) 0.025(2) -0.0052(18) C7 0.050(2) 0.030(2) 0.050(3) 0.0133(18) 0.0326(19) 0.0029(18) C8 0.035(2) 0.047(2) 0.037(2) -0.0051(18) 0.0193(19) -0.0032(18) C9 0.040(2) 0.046(2) 0.052(3) 0.017(2) 0.030(2) 0.0128(18) C10 0.050(3) 0.058(3) 0.037(2) -0.003(2) 0.022(2) 0.001(2) C11 0.041(2) 0.040(2) 0.051(3) 0.006(2) 0.027(2) -0.0074(18) C12 0.049(3) 0.049(3) 0.057(3) -0.004(2) 0.033(2) -0.001(2) C13 0.082(4) 0.046(3) 0.057(3) -0.005(2) 0.050(3) 0.005(2) C14 0.043(3) 0.057(3) 0.060(3) 0.001(2) 0.031(2) -0.007(2) C15 0.033(2) 0.046(3) 0.043(2) 0.012(2) 0.0135(19) -0.0047(19) C16 0.033(2) 0.057(3) 0.038(2) 0.001(2) 0.0084(19) 0.0077(18) C17 0.063(3) 0.078(4) 0.058(3) 0.014(3) 0.022(3) 0.007(3) C18 0.065(3) 0.060(3) 0.082(4) 0.003(3) 0.038(3) -0.010(2) C19 0.044(2) 0.059(3) 0.048(3) 0.003(2) 0.023(2) 0.005(2) C20 0.066(7) 0.057(6) 0.081(8) -0.004(5) 0.033(6) 0.019(5) C21 0.044(5) 0.089(7) 0.044(5) -0.017(5) 0.020(4) -0.008(5) C22 0.042(3) 0.099(4) 0.050(3) 0.006(3) 0.013(2) -0.009(2) C23 0.093(4) 0.117(5) 0.066(4) 0.016(3) 0.048(3) 0.012(4) C24 0.052(3) 0.094(4) 0.079(4) 0.035(3) 0.015(3) 0.013(3) C25 0.041(3) 0.059(3) 0.057(3) -0.002(2) 0.025(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.966(3) . ? Zn1 O4 1.980(3) 4_475 ? Zn1 N3 2.032(4) . ? Zn1 N1 2.041(3) . ? S1 C4 1.721(4) . ? S1 C7 1.743(4) . ? S2 C11 1.690(4) . ? S2 C14 1.728(5) . ? O1 C15 1.277(5) . ? O2 C15 1.226(5) . ? O3 C25 1.254(5) . ? O4 C25 1.168(5) . ? O4 Zn1 1.980(3) 4_676 ? N1 C1 1.292(5) . ? N1 C2 1.354(5) . ? N2 C1 1.346(5) . ? N2 C3 1.357(5) . ? N2 C4 1.455(5) . ? N3 C8 1.328(5) . ? N3 C9 1.347(5) . ? N4 C8 1.327(5) . ? N4 C11 1.413(5) . ? N4 C10 1.463(5) . ? C1 H1 0.9300 . ? C2 C3 1.366(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.330(6) . ? C5 C6 1.407(6) . ? C5 H5 0.9300 . ? C6 C7 1.370(6) . ? C6 H6 0.9300 . ? C7 C7 1.400(8) 3_676 ? C8 H8 0.9300 . ? C9 C10 1.350(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.353(6) . ? C12 C13 1.373(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(6) . ? C13 H13 0.9300 . ? C14 C14 1.514(9) 3_565 ? C15 C16 1.533(5) . ? C16 C21 1.461(10) . ? C16 C17 1.527(6) . ? C16 C22 1.520(6) . ? C16 H16A 0.9695 . ? C17 C18 1.521(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.540(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C22 1.533(6) . ? C19 C20 1.544(10) . ? C19 C25 1.556(6) . ? C19 H19A 0.9594 . ? C20 C21 1.551(12) . ? C20 H19A 0.6652 . ? C20 H20A 0.9701 . ? C20 H20B 0.9702 . ? C20 H20C 0.9603 . ? C20 H21C 0.6414 . ? C21 H20C 0.6090 . ? C21 H21C 0.9096 . ? C21 H16A 0.6170 . ? C21 H21A 0.9702 . ? C21 H21B 0.9705 . ? C22 C23 1.534(8) . ? C22 C24 1.545(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O4 108.90(12) . 4_475 ? O1 Zn1 N3 121.33(14) . . ? O4 Zn1 N3 103.92(12) 4_475 . ? O1 Zn1 N1 95.18(13) . . ? O4 Zn1 N1 127.40(12) 4_475 . ? N3 Zn1 N1 101.71(14) . . ? C4 S1 C7 90.75(19) . . ? C11 S2 C14 89.6(2) . . ? C15 O1 Zn1 116.6(3) . . ? C25 O4 Zn1 109.4(3) . 4_676 ? C1 N1 C2 106.3(3) . . ? C1 N1 Zn1 125.2(3) . . ? C2 N1 Zn1 128.3(3) . . ? C1 N2 C3 105.5(3) . . ? C1 N2 C4 128.5(3) . . ? C3 N2 C4 125.5(3) . . ? C8 N3 C9 106.8(4) . . ? C8 N3 Zn1 127.0(3) . . ? C9 N3 Zn1 126.0(3) . . ? C8 N4 C11 128.2(4) . . ? C8 N4 C10 106.2(3) . . ? C11 N4 C10 125.5(4) . . ? N1 C1 N2 112.1(4) . . ? N1 C1 H1 123.9 . . ? N2 C1 H1 123.9 . . ? N1 C2 C3 108.5(4) . . ? N1 C2 H2 125.8 . . ? C3 C2 H2 125.8 . . ? N2 C3 C2 106.8(4) . . ? N2 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? C5 C4 N2 127.2(4) . . ? C5 C4 S1 113.8(3) . . ? N2 C4 S1 119.0(3) . . ? C4 C5 C6 111.1(4) . . ? C4 C5 H5 124.4 . . ? C6 C5 H5 124.4 . . ? C7 C6 C5 115.0(4) . . ? C7 C6 H6 122.5 . . ? C5 C6 H6 122.5 . . ? C6 C7 C7 130.7(5) . 3_676 ? C6 C7 S1 109.2(3) . . ? C7 C7 S1 120.0(4) 3_676 . ? N4 C8 N3 111.7(4) . . ? N4 C8 H8 124.2 . . ? N3 C8 H8 124.2 . . ? N3 C9 C10 111.9(4) . . ? N3 C9 H9 124.1 . . ? C10 C9 H9 124.1 . . ? C9 C10 N4 103.4(4) . . ? C9 C10 H10 128.3 . . ? N4 C10 H10 128.3 . . ? C12 C11 N4 127.7(4) . . ? C12 C11 S2 113.8(3) . . ? N4 C11 S2 118.3(3) . . ? C11 C12 C13 112.8(4) . . ? C11 C12 H12 123.6 . . ? C13 C12 H12 123.6 . . ? C12 C13 C14 111.8(4) . . ? C12 C13 H13 124.1 . . ? C14 C13 H13 124.1 . . ? C13 C14 C14 130.7(5) . 3_565 ? C13 C14 S2 112.0(3) . . ? C14 C14 S2 117.3(4) 3_565 . ? O2 C15 O1 124.9(4) . . ? O2 C15 C16 120.0(4) . . ? O1 C15 C16 114.9(4) . . ? C21 C16 C17 112.4(5) . . ? C21 C16 C22 94.6(5) . . ? C17 C16 C22 92.2(4) . . ? C21 C16 C15 125.9(5) . . ? C17 C16 C15 113.0(4) . . ? C22 C16 C15 111.4(4) . . ? C17 C16 H16A 112.7 . . ? C22 C16 H16A 112.4 . . ? C15 C16 H16A 113.4 . . ? C18 C17 C16 106.3(4) . . ? C18 C17 H17A 110.5 . . ? C16 C17 H17A 110.5 . . ? C18 C17 H17B 110.5 . . ? C16 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C17 C18 C19 107.3(4) . . ? C17 C18 H18A 110.3 . . ? C19 C18 H18A 110.3 . . ? C17 C18 H18B 110.3 . . ? C19 C18 H18B 110.3 . . ? H18A C18 H18B 108.5 . . ? C22 C19 C18 93.2(4) . . ? C22 C19 C20 97.2(5) . . ? C18 C19 C20 106.7(5) . . ? C22 C19 C25 110.9(4) . . ? C18 C19 C25 119.6(4) . . ? C20 C19 C25 122.8(5) . . ? C22 C19 H19A 110.9 . . ? C18 C19 H19A 110.8 . . ? C25 C19 H19A 110.3 . . ? C19 C20 C21 102.3(8) . . ? C21 C20 H19A 124.2 . . ? C19 C20 H20A 112.1 . . ? C21 C20 H20A 112.1 . . ? H19A C20 H20A 101.3 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 111.4 . . ? H19A C20 H20B 97.1 . . ? H20A C20 H20B 109.2 . . ? C19 C20 H20C 109.3 . . ? H19A C20 H20C 131.1 . . ? H20A C20 H20C 108.2 . . ? H20B C20 H20C 108.4 . . ? C19 C20 H21C 101.4 . . ? H19A C20 H21C 123.3 . . ? H20A C20 H21C 112.4 . . ? H20B C20 H21C 111.9 . . ? C16 C21 C20 111.1(7) . . ? C16 C21 H20C 122.2 . . ? C16 C21 H21C 110.5 . . ? C20 C21 H16A 136.7 . . ? H20C C21 H16A 147.0 . . ? H21C C21 H16A 136.1 . . ? C16 C21 H21A 109.2 . . ? C20 C21 H21A 109.2 . . ? H20C C21 H21A 103.2 . . ? H21C C21 H21A 109.7 . . ? H16A C21 H21A 84.8 . . ? C16 C21 H21B 110.5 . . ? C20 C21 H21B 108.7 . . ? H20C C21 H21B 102.9 . . ? H21C C21 H21B 108.9 . . ? H16A C21 H21B 104.9 . . ? H21A C21 H21B 108.0 . . ? C16 C22 C23 103.3(4) . . ? C16 C22 C19 104.4(4) . . ? C23 C22 C19 124.8(5) . . ? C16 C22 C24 114.5(4) . . ? C23 C22 C24 102.2(5) . . ? C19 C22 C24 108.0(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C25 O3 120.1(4) . . ? O4 C25 C19 118.0(4) . . ? O3 C25 C19 121.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O1 C15 84.0(3) 4_475 . . . ? N3 Zn1 O1 C15 -36.4(3) . . . . ? N1 Zn1 O1 C15 -143.5(3) . . . . ? O1 Zn1 N1 C1 15.2(4) . . . . ? O4 Zn1 N1 C1 133.9(3) 4_475 . . . ? N3 Zn1 N1 C1 -108.3(4) . . . . ? O1 Zn1 N1 C2 -159.4(4) . . . . ? O4 Zn1 N1 C2 -40.8(4) 4_475 . . . ? N3 Zn1 N1 C2 77.1(4) . . . . ? O1 Zn1 N3 C8 7.4(4) . . . . ? O4 Zn1 N3 C8 -115.4(3) 4_475 . . . ? N1 Zn1 N3 C8 110.9(3) . . . . ? O1 Zn1 N3 C9 -167.0(3) . . . . ? O4 Zn1 N3 C9 70.2(3) 4_475 . . . ? N1 Zn1 N3 C9 -63.4(3) . . . . ? C2 N1 C1 N2 -6.9(5) . . . . ? Zn1 N1 C1 N2 177.5(3) . . . . ? C3 N2 C1 N1 9.0(5) . . . . ? C4 N2 C1 N1 -178.7(4) . . . . ? C1 N1 C2 C3 2.0(5) . . . . ? Zn1 N1 C2 C3 177.4(3) . . . . ? C1 N2 C3 C2 -7.2(5) . . . . ? C4 N2 C3 C2 -179.8(4) . . . . ? N1 C2 C3 N2 3.4(5) . . . . ? C1 N2 C4 C5 163.3(4) . . . . ? C3 N2 C4 C5 -25.8(7) . . . . ? C1 N2 C4 S1 -15.6(6) . . . . ? C3 N2 C4 S1 155.3(4) . . . . ? C7 S1 C4 C5 4.0(4) . . . . ? C7 S1 C4 N2 -177.0(3) . . . . ? N2 C4 C5 C6 176.0(4) . . . . ? S1 C4 C5 C6 -5.0(5) . . . . ? C4 C5 C6 C7 3.7(6) . . . . ? C5 C6 C7 C7 175.9(6) . . . 3_676 ? C5 C6 C7 S1 -0.8(5) . . . . ? C4 S1 C7 C6 -1.7(3) . . . . ? C4 S1 C7 C7 -178.7(5) . . . 3_676 ? C11 N4 C8 N3 179.4(4) . . . . ? C10 N4 C8 N3 0.6(4) . . . . ? C9 N3 C8 N4 -0.7(5) . . . . ? Zn1 N3 C8 N4 -176.0(3) . . . . ? C8 N3 C9 C10 0.6(5) . . . . ? Zn1 N3 C9 C10 175.9(3) . . . . ? N3 C9 C10 N4 -0.2(5) . . . . ? C8 N4 C10 C9 -0.2(4) . . . . ? C11 N4 C10 C9 -179.1(4) . . . . ? C8 N4 C11 C12 151.3(4) . . . . ? C10 N4 C11 C12 -30.1(6) . . . . ? C8 N4 C11 S2 -34.7(5) . . . . ? C10 N4 C11 S2 143.9(3) . . . . ? C14 S2 C11 C12 -2.7(4) . . . . ? C14 S2 C11 N4 -177.5(3) . . . . ? N4 C11 C12 C13 176.8(4) . . . . ? S2 C11 C12 C13 2.5(5) . . . . ? C11 C12 C13 C14 -0.8(6) . . . . ? C12 C13 C14 C14 178.4(6) . . . 3_565 ? C12 C13 C14 S2 -1.2(5) . . . . ? C11 S2 C14 C13 2.2(4) . . . . ? C11 S2 C14 C14 -177.5(5) . . . 3_565 ? Zn1 O1 C15 O2 -7.8(6) . . . . ? Zn1 O1 C15 C16 177.7(3) . . . . ? O2 C15 C16 C21 -140.0(7) . . . . ? O1 C15 C16 C21 34.8(8) . . . . ? O2 C15 C16 C17 4.8(6) . . . . ? O1 C15 C16 C17 179.6(4) . . . . ? O2 C15 C16 C22 107.0(5) . . . . ? O1 C15 C16 C22 -78.2(5) . . . . ? C21 C16 C17 C18 -57.9(7) . . . . ? C22 C16 C17 C18 38.0(5) . . . . ? C15 C16 C17 C18 152.4(4) . . . . ? C16 C17 C18 C19 -7.0(6) . . . . ? C17 C18 C19 C22 -27.3(5) . . . . ? C17 C18 C19 C20 71.2(7) . . . . ? C17 C18 C19 C25 -143.6(5) . . . . ? C22 C19 C20 C21 27.7(8) . . . . ? C18 C19 C20 C21 -67.8(8) . . . . ? C25 C19 C20 C21 148.3(6) . . . . ? C17 C16 C21 C20 60.6(9) . . . . ? C22 C16 C21 C20 -33.7(8) . . . . ? C15 C16 C21 C20 -154.4(7) . . . . ? C19 C20 C21 C16 3.9(10) . . . . ? C21 C16 C22 C23 -175.0(5) . . . . ? C17 C16 C22 C23 72.3(5) . . . . ? C15 C16 C22 C23 -43.5(5) . . . . ? C21 C16 C22 C19 53.2(6) . . . . ? C17 C16 C22 C19 -59.5(4) . . . . ? C15 C16 C22 C19 -175.3(4) . . . . ? C21 C16 C22 C24 -64.7(6) . . . . ? C17 C16 C22 C24 -177.4(5) . . . . ? C15 C16 C22 C24 66.8(6) . . . . ? C18 C19 C22 C16 55.3(5) . . . . ? C20 C19 C22 C16 -52.1(6) . . . . ? C25 C19 C22 C16 178.7(4) . . . . ? C18 C19 C22 C23 -62.6(6) . . . . ? C20 C19 C22 C23 -170.0(6) . . . . ? C25 C19 C22 C23 60.8(6) . . . . ? C18 C19 C22 C24 177.5(5) . . . . ? C20 C19 C22 C24 70.2(6) . . . . ? C25 C19 C22 C24 -59.0(6) . . . . ? Zn1 O4 C25 O3 -1.6(5) 4_676 . . . ? Zn1 O4 C25 C19 -177.6(3) 4_676 . . . ? C22 C19 C25 O4 106.7(5) . . . . ? C18 C19 C25 O4 -146.6(5) . . . . ? C20 C19 C25 O4 -7.2(8) . . . . ? C22 C19 C25 O3 -69.2(6) . . . . ? C18 C19 C25 O3 37.4(7) . . . . ? C20 C19 C25 O3 176.9(6) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.500 234 33 ' ' 2 0.500 0.000 1.000 234 33 ' ' _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.429 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 963197'