# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email cprao@chem.iitb.ac.in _publ_contact_author_name 'Dr Chebrolu Pulla Rao' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Bombay Mumbai 400 076 INDIA ; _publ_contact_author_fax '091-022-2572 3480, 091-022-2572 3245' _publ_contact_author_phone '091-022-2576 7162, 091-022-2576 8162' _publ_section_title ; mplexation behaviour of hexadentate ligands possessing N2O4 and N2O2S2 cores: differential reactivity towards Co(II), Ni(II) and Zn(II) salts and structures of the products ; loop_ _publ_author_name 'Chebrolu Pulla Rao' 'K. Nattinen' 'Gudneppanavar Rajsekhar' 'K. Rissanen' 'P. Saarenketo' data_cpr090 _database_code_CSD 172099 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N2 O2 S2' _chemical_formula_weight 484.61 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_Int_Tables_number 14 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 10.716(1) _cell_length_b 16.811(1) _cell_length_c 13.097(1) _cell_angle_alpha 90.00 _cell_angle_beta 104.23(1) _cell_angle_gamma 90.00 _cell_volume 2287.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm; 1 deg., 100 sec./deg., mos. = 0.572(2) ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12704 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4014 _reflns_number_gt 3412 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Platon _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0893P)^2^+3.3780P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4014 _refine_ls_number_parameters 227 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.054 _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 O1A O 0.1096(2) 0.22572(15) 0.91356(16) 0.0400(6) Uani 1 1 d . . . H1A H 0.1569 0.1983 0.8847 0.060 Uiso 1 1 calc R . . C2A C 0.0188(3) 0.26294(18) 0.8387(2) 0.0304(7) Uani 1 1 d . . . C3A C -0.0711(3) 0.3107(2) 0.8699(3) 0.0380(8) Uani 1 1 d . . . H3A H -0.0685 0.3158 0.9427 0.046 Uiso 1 1 calc R . . C4A C -0.1644(3) 0.3508(2) 0.7958(3) 0.0383(8) Uani 1 1 d . . . H4A H -0.2248 0.3838 0.8180 0.046 Uiso 1 1 calc R . . C5A C -0.1701(3) 0.3432(2) 0.6896(3) 0.0415(8) Uani 1 1 d . . . H5A H -0.2334 0.3713 0.6390 0.050 Uiso 1 1 calc R . . C6A C -0.0832(3) 0.29445(19) 0.6579(2) 0.0349(7) Uani 1 1 d . . . H6A H -0.0884 0.2883 0.5848 0.042 Uiso 1 1 calc R . . C7A C 0.0126(3) 0.25393(17) 0.7312(2) 0.0284(6) Uani 1 1 d . B . C8A C 0.1002(3) 0.20220(18) 0.6927(2) 0.0300(7) Uani 1 1 d . . . H8A H 0.0909 0.1986 0.6188 0.036 Uiso 1 1 calc R A 1 N9A N 0.1897(3) 0.1610(3) 0.7537(4) 0.0248(6) Uiso 0.802(7) 1 d PD B 1 C10A C 0.2752(2) 0.11018(14) 0.7158(2) 0.0235(6) Uiso 0.802(7) 1 d PGD B 1 C11A C 0.2930(3) 0.11579(17) 0.6145(2) 0.0306(8) Uiso 0.802(7) 1 d PGD B 1 H11A H 0.2473 0.1547 0.5672 0.037 Uiso 0.802(7) 1 calc PR B 1 C12A C 0.3777(3) 0.06446(19) 0.58237(18) 0.0340(9) Uiso 0.802(7) 1 d PGD B 1 H12A H 0.3899 0.0683 0.5131 0.041 Uiso 0.802(7) 1 calc PR B 1 C13A C 0.4445(3) 0.00752(19) 0.6516(2) 0.0340(8) Uiso 0.802(7) 1 d PGD B 1 H13A H 0.5024 -0.0276 0.6297 0.041 Uiso 0.802(7) 1 calc PR B 1 C14A C 0.4267(3) 0.00191(16) 0.7530(2) 0.0301(7) Uiso 0.802(7) 1 d PGD B 1 H14A H 0.4723 -0.0370 0.8003 0.036 Uiso 0.802(7) 1 calc PR B 1 C15A C 0.34199(18) 0.05324(14) 0.78506(16) 0.0233(7) Uiso 0.802(7) 1 d PGD B 1 S16A S 0.31294(12) 0.05047(14) 0.91289(8) 0.0234(3) Uiso 0.802(7) 1 d PD B 1 C17A C 0.4340(3) -0.0197(2) 0.9832(3) 0.0266(9) Uiso 0.802(7) 1 d PD . 1 H17A H 0.4085 -0.0397 1.0462 0.032 Uiso 0.802(7) 1 calc PR B 1 H17B H 0.4386 -0.0657 0.9370 0.032 Uiso 0.802(7) 1 calc PR B 1 N9B N 0.1778(8) 0.1650(10) 0.7612(16) 0.0248(6) Uiso 0.198(7) 1 d PD B 2 C10B C 0.2585(8) 0.1177(6) 0.7126(7) 0.0235(6) Uiso 0.198(7) 1 d PGD B 2 C11B C 0.2633(12) 0.1159(7) 0.6075(7) 0.0306(8) Uiso 0.198(7) 1 d PGD B 2 H11B H 0.2079 0.1491 0.5575 0.037 Uiso 0.198(7) 1 calc PR B 2 C12B C 0.3492(14) 0.0654(8) 0.5756(7) 0.0340(9) Uiso 0.198(7) 1 d PGD B 2 H12B H 0.3525 0.0641 0.5038 0.041 Uiso 0.198(7) 1 calc PR B 2 C13B C 0.4302(13) 0.0167(8) 0.6488(9) 0.0340(8) Uiso 0.198(7) 1 d PGD B 2 H13B H 0.4889 -0.0178 0.6269 0.041 Uiso 0.198(7) 1 calc PR B 2 C14B C 0.4254(10) 0.0186(7) 0.7538(8) 0.0301(7) Uiso 0.198(7) 1 d PGD B 2 H14B H 0.4808 -0.0147 0.8038 0.036 Uiso 0.198(7) 1 calc PR B 2 C15B C 0.3395(6) 0.0691(5) 0.7857(6) 0.0233(7) Uiso 0.198(7) 1 d PGD B 2 S16B S 0.3292(5) 0.0739(5) 0.9197(3) 0.0234(3) Uiso 0.198(7) 1 d PD B 2 C17B C 0.4287(8) -0.0048(10) 0.9966(14) 0.0266(9) Uiso 0.198(7) 1 d PD . 2 H17C H 0.4154 -0.0048 1.0688 0.032 Uiso 0.198(7) 1 calc PR B 2 H17D H 0.3997 -0.0569 0.9643 0.032 Uiso 0.198(7) 1 calc PR B 2 O1C O 0.5772(2) 0.21321(15) 0.90963(17) 0.0426(6) Uani 1 1 d . . . H1C H 0.6273 0.1882 0.8809 0.064 Uiso 1 1 calc R . . C2C C 0.4963(3) 0.25804(18) 0.8369(2) 0.0323(7) Uani 1 1 d . . . C3C C 0.4035(3) 0.3034(2) 0.8683(3) 0.0383(8) Uani 1 1 d . . . H3C H 0.3975 0.3015 0.9395 0.046 Uiso 1 1 calc R . . C4C C 0.3195(3) 0.3515(2) 0.7962(3) 0.0391(8) Uani 1 1 d . . . H4C H 0.2579 0.3832 0.8187 0.047 Uiso 1 1 calc R . . C5C C 0.3255(3) 0.3535(2) 0.6924(3) 0.0391(8) Uani 1 1 d . . . H5C H 0.2670 0.3857 0.6432 0.047 Uiso 1 1 calc R . . C6C C 0.4169(3) 0.30836(19) 0.6597(2) 0.0337(7) Uani 1 1 d . . . H6C H 0.4211 0.3105 0.5881 0.040 Uiso 1 1 calc R . . C7C C 0.5031(3) 0.25970(18) 0.7308(2) 0.0300(7) Uani 1 1 d . D . C8C C 0.5944(3) 0.21141(18) 0.6924(2) 0.0303(7) Uani 1 1 d . . . H8C H 0.6018 0.2186 0.6222 0.036 Uiso 1 1 calc R C 3 N9C N 0.6670(4) 0.1579(3) 0.7526(5) 0.0276(7) Uiso 0.753(8) 1 d PD D 3 C10C C 0.7568(2) 0.11188(16) 0.7125(2) 0.0272(6) Uiso 0.753(8) 1 d PGD D 3 C11C C 0.7512(3) 0.1024(2) 0.6060(2) 0.0353(9) Uiso 0.753(8) 1 d PGD D 3 H11C H 0.6846 0.1273 0.5546 0.042 Uiso 0.753(8) 1 calc PR D 3 C12C C 0.8431(3) 0.0564(2) 0.5748(2) 0.0362(9) Uiso 0.753(8) 1 d PGD D 3 H12C H 0.8393 0.0500 0.5020 0.043 Uiso 0.753(8) 1 calc PR D 3 C13C C 0.9406(3) 0.0200(2) 0.6500(3) 0.0324(8) Uiso 0.753(8) 1 d PGD D 3 H13C H 1.0034 -0.0115 0.6286 0.039 Uiso 0.753(8) 1 calc PR D 3 C14C C 0.9462(3) 0.02944(18) 0.7564(2) 0.0304(8) Uiso 0.753(8) 1 d PGD D 3 H14C H 1.0128 0.0045 0.8078 0.036 Uiso 0.753(8) 1 calc PR D 3 C15C C 0.8543(2) 0.07539(13) 0.7877(2) 0.0249(6) Uiso 0.753(8) 1 d PGD D 3 S16C S 0.85322(15) 0.09098(15) 0.92169(10) 0.0241(3) Uiso 0.753(8) 1 d PD D 3 C17C C 1.0032(6) 0.0449(3) 0.9958(7) 0.0319(9) Uiso 0.753(8) 1 d PD . 3 H17E H 1.0729 0.0588 0.9615 0.038 Uiso 0.753(8) 1 calc PR D 3 H17F H 1.0261 0.0677 1.0677 0.038 Uiso 0.753(8) 1 calc PR D 3 N9D N 0.6692(8) 0.1668(9) 0.7475(15) 0.0276(7) Uiso 0.247(8) 1 d PD D 4 C10D C 0.7543(7) 0.1182(5) 0.7086(7) 0.0272(6) Uiso 0.247(8) 1 d PGD D 4 C11D C 0.7541(9) 0.1191(6) 0.6025(7) 0.0353(9) Uiso 0.247(8) 1 d PGD D 4 H11D H 0.6962 0.1528 0.5551 0.042 Uiso 0.247(8) 1 calc PR D 4 C12D C 0.8388(11) 0.0708(7) 0.5656(6) 0.0362(9) Uiso 0.247(8) 1 d PGD D 4 H12D H 0.8387 0.0714 0.4931 0.043 Uiso 0.247(8) 1 calc PR D 4 C13D C 0.9237(11) 0.0215(6) 0.6349(8) 0.0324(8) Uiso 0.247(8) 1 d PGD D 4 H13D H 0.9815 -0.0116 0.6097 0.039 Uiso 0.247(8) 1 calc PR D 4 C14D C 0.9238(9) 0.0205(5) 0.7411(7) 0.0304(8) Uiso 0.247(8) 1 d PGD D 4 H14D H 0.9818 -0.0132 0.7885 0.036 Uiso 0.247(8) 1 calc PR D 4 C15D C 0.8392(6) 0.0688(4) 0.7779(6) 0.0249(6) Uiso 0.247(8) 1 d PGD D 4 S16D S 0.8360(5) 0.0695(5) 0.9143(3) 0.0241(3) Uiso 0.247(8) 1 d PD D 4 C17D C 1.0005(18) 0.0435(6) 0.986(2) 0.0319(9) Uiso 0.247(8) 1 d PD . 4 H17G H 1.0616 0.0535 0.9421 0.038 Uiso 0.247(8) 1 calc PR D 4 H17H H 1.0270 0.0758 1.0513 0.038 Uiso 0.247(8) 1 calc PR D 4 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 O1A 0.0404(13) 0.0488(14) 0.0288(11) 0.0046(10) 0.0044(10) 0.0151(11) C2A 0.0290(15) 0.0270(15) 0.0326(16) 0.0039(12) 0.0028(12) 0.0005(12) C3A 0.0378(18) 0.0386(18) 0.0370(17) 0.0001(14) 0.0081(14) 0.0057(14) C4A 0.0325(17) 0.0330(18) 0.049(2) -0.0003(14) 0.0088(15) 0.0030(14) C5A 0.0331(17) 0.0389(19) 0.047(2) 0.0112(15) -0.0001(15) 0.0058(14) C6A 0.0353(17) 0.0354(18) 0.0301(16) 0.0060(13) 0.0004(13) 0.0027(14) C7A 0.0285(15) 0.0226(15) 0.0313(16) 0.0030(11) 0.0021(12) -0.0036(12) C8A 0.0344(16) 0.0274(15) 0.0251(15) -0.0005(12) 0.0013(12) -0.0026(12) O1C 0.0490(14) 0.0469(15) 0.0304(12) 0.0055(10) 0.0072(10) 0.0148(11) C2C 0.0345(16) 0.0285(16) 0.0314(16) -0.0007(12) 0.0031(13) -0.0041(13) C3C 0.0386(18) 0.0365(18) 0.0396(18) -0.0034(14) 0.0092(14) -0.0017(14) C4C 0.0307(17) 0.0317(17) 0.054(2) -0.0065(15) 0.0092(15) -0.0018(14) C5C 0.0289(16) 0.0325(17) 0.049(2) 0.0059(15) -0.0029(14) -0.0003(13) C6C 0.0327(16) 0.0317(17) 0.0320(16) 0.0030(13) -0.0011(13) -0.0035(13) C7C 0.0309(15) 0.0254(15) 0.0306(16) -0.0004(12) 0.0014(12) -0.0054(12) C8C 0.0285(15) 0.0337(17) 0.0257(15) 0.0005(12) 0.0011(12) -0.0038(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C2A 1.353(4) . ? O1A H1A 0.8400 . ? C2A C3A 1.391(4) . ? C2A C7A 1.401(4) . ? C3A C4A 1.386(5) . ? C3A H3A 0.9500 . ? C4A C5A 1.383(5) . ? C4A H4A 0.9500 . ? C5A C6A 1.379(5) . ? C5A H5A 0.9500 . ? C6A C7A 1.398(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.458(4) . ? C8A N9B 1.233(18) . ? C8A N9A 1.289(5) . ? C8A H8A 0.9500 . ? N9A C10A 1.428(4) . ? C10A C11A 1.3900 . ? C10A C15A 1.3900 . ? C11A C12A 1.3900 . ? C11A H11A 0.9500 . ? C12A C13A 1.3900 . ? C12A H12A 0.9500 . ? C13A C14A 1.3900 . ? C13A H13A 0.9500 . ? C14A C15A 1.3900 . ? C14A H14A 0.9500 . ? C15A S16A 1.777(2) . ? S16A C17A 1.826(4) . ? C17A C17A 1.526(7) 3_657 ? C17A H17A 0.9900 . ? C17A H17B 0.9900 . ? N9B C10B 1.433(12) . ? C10B C11B 1.3900 . ? C10B C15B 1.3900 . ? C11B C12B 1.3900 . ? C11B H11B 0.9500 . ? C12B C13B 1.3900 . ? C12B H12B 0.9500 . ? C13B C14B 1.3900 . ? C13B H13B 0.9500 . ? C14B C15B 1.3900 . ? C14B H14B 0.9500 . ? C15B S16B 1.786(9) . ? S16B C17B 1.837(13) . ? C17B C17B 1.517(17) 3_657 ? C17B H17C 0.9900 . ? C17B H17D 0.9900 . ? O1C C2C 1.350(4) . ? O1C H1C 0.8400 . ? C2C C3C 1.393(5) . ? C2C C7C 1.410(4) . ? C3C C4C 1.392(5) . ? C3C H3C 0.9500 . ? C4C C5C 1.378(5) . ? C4C H4C 0.9500 . ? C5C C6C 1.387(5) . ? C5C H5C 0.9500 . ? C6C C7C 1.403(4) . ? C6C H6C 0.9500 . ? C7C C8C 1.452(4) . ? C8C N9D 1.201(16) . ? C8C N9C 1.318(6) . ? C8C H8C 0.9500 . ? N9C C10C 1.432(4) . ? C10C C11C 1.3900 . ? C10C C15C 1.3900 . ? C11C C12C 1.3900 . ? C11C H11C 0.9500 . ? C12C C13C 1.3900 . ? C12C H12C 0.9500 . ? C13C C14C 1.3900 . ? C13C H13C 0.9500 . ? C14C C15C 1.3900 . ? C14C H14C 0.9500 . ? C15C S16C 1.777(3) . ? S16C C17C 1.832(5) . ? C17C C17C 1.517(8) 3_757 ? C17C H17E 0.9900 . ? C17C H17F 0.9900 . ? N9D C10D 1.410(12) . ? C10D C11D 1.3900 . ? C10D C15D 1.3900 . ? C11D C12D 1.3900 . ? C11D H11D 0.9500 . ? C12D C13D 1.3900 . ? C12D H12D 0.9500 . ? C13D C14D 1.3900 . ? C13D H13D 0.9500 . ? C14D C15D 1.3900 . ? C14D H14D 0.9500 . ? C15D S16D 1.794(8) . ? S16D C17D 1.836(15) . ? C17D C17D 1.506(17) 3_757 ? C17D H17G 0.9900 . ? C17D H17H 0.9900 . ? 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 C2A O1A H1A 109.5 . . ? O1A C2A C3A 118.7(3) . . ? O1A C2A C7A 121.8(3) . . ? C3A C2A C7A 119.5(3) . . ? C4A C3A C2A 120.5(3) . . ? C4A C3A H3A 119.8 . . ? C2A C3A H3A 119.8 . . ? C5A C4A C3A 120.4(3) . . ? C5A C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? C6A C5A C4A 119.5(3) . . ? C6A C5A H5A 120.3 . . ? C4A C5A H5A 120.3 . . ? C5A C6A C7A 121.2(3) . . ? C5A C6A H6A 119.4 . . ? C7A C6A H6A 119.4 . . ? C6A C7A C2A 118.9(3) . . ? C6A C7A C8A 118.6(3) . . ? C2A C7A C8A 122.4(3) . . ? N9B C8A N9A 8.3(9) . . ? N9B C8A C7A 115.3(8) . . ? N9A C8A C7A 123.3(3) . . ? N9B C8A H8A 126.3 . . ? N9A C8A H8A 118.3 . . ? C7A C8A H8A 118.3 . . ? C8A N9A C10A 123.3(4) . . ? C11A C10A C15A 120.0 . . ? C11A C10A N9A 122.8(2) . . ? C15A C10A N9A 117.2(2) . . ? C12A C11A C10A 120.0 . . ? C12A C11A H11A 120.0 . . ? C10A C11A H11A 120.0 . . ? C11A C12A C13A 120.0 . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C14A C13A C12A 120.0 . . ? C14A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? C13A C14A C15A 120.0 . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C14A C15A C10A 120.0 . . ? C14A C15A S16A 123.18(12) . . ? C10A C15A S16A 116.82(12) . . ? C15A S16A C17A 102.98(16) . . ? C17A C17A S16A 111.0(4) 3_657 . ? C17A C17A H17A 109.4 3_657 . ? S16A C17A H17A 109.4 . . ? C17A C17A H17B 109.4 3_657 . ? S16A C17A H17B 109.4 . . ? H17A C17A H17B 108.0 . . ? C8A N9B C10B 109.3(14) . . ? C11B C10B C15B 120.0 . . ? C11B C10B N9B 128.7(9) . . ? C15B C10B N9B 111.3(9) . . ? C12B C11B C10B 120.0 . . ? C12B C11B H11B 120.0 . . ? C10B C11B H11B 120.0 . . ? C13B C12B C11B 120.0 . . ? C13B C12B H12B 120.0 . . ? C11B C12B H12B 120.0 . . ? C12B C13B C14B 120.0 . . ? C12B C13B H13B 120.0 . . ? C14B C13B H13B 120.0 . . ? C13B C14B C15B 120.0 . . ? C13B C14B H14B 120.0 . . ? C15B C14B H14B 120.0 . . ? C14B C15B C10B 120.0 . . ? C14B C15B S16B 121.9(3) . . ? C10B C15B S16B 118.1(3) . . ? C15B S16B C17B 109.8(6) . . ? C17B C17B S16B 113.4(13) 3_657 . ? C17B C17B H17C 108.9 3_657 . ? S16B C17B H17C 108.9 . . ? C17B C17B H17D 108.9 3_657 . ? S16B C17B H17D 108.9 . . ? H17C C17B H17D 107.7 . . ? C2C O1C H1C 109.5 . . ? O1C C2C C3C 118.5(3) . . ? O1C C2C C7C 121.8(3) . . ? C3C C2C C7C 119.6(3) . . ? C4C C3C C2C 120.4(3) . . ? C4C C3C H3C 119.8 . . ? C2C C3C H3C 119.8 . . ? C5C C4C C3C 120.3(3) . . ? C5C C4C H4C 119.9 . . ? C3C C4C H4C 119.9 . . ? C4C C5C C6C 120.0(3) . . ? C4C C5C H5C 120.0 . . ? C6C C5C H5C 120.0 . . ? C5C C6C C7C 120.9(3) . . ? C5C C6C H6C 119.5 . . ? C7C C6C H6C 119.5 . . ? C6C C7C C2C 118.7(3) . . ? C6C C7C C8C 119.1(3) . . ? C2C C7C C8C 122.2(3) . . ? N9D C8C N9C 5.5(7) . . ? N9D C8C C7C 123.2(8) . . ? N9C C8C C7C 121.5(3) . . ? N9D C8C H8C 117.3 . . ? N9C C8C H8C 119.2 . . ? C7C C8C H8C 119.2 . . ? C8C N9C C10C 120.0(5) . . ? C11C C10C C15C 120.0 . . ? C11C C10C N9C 124.3(3) . . ? C15C C10C N9C 115.7(3) . . ? C12C C11C C10C 120.0 . . ? C12C C11C H11C 120.0 . . ? C10C C11C H11C 120.0 . . ? C13C C12C C11C 120.0 . . ? C13C C12C H12C 120.0 . . ? C11C C12C H12C 120.0 . . ? C12C C13C C14C 120.0 . . ? C12C C13C H13C 120.0 . . ? C14C C13C H13C 120.0 . . ? C15C C14C C13C 120.0 . . ? C15C C14C H14C 120.0 . . ? C13C C14C H14C 120.0 . . ? C14C C15C C10C 120.0 . . ? C14C C15C S16C 123.35(14) . . ? C10C C15C S16C 116.65(14) . . ? C15C S16C C17C 104.1(3) . . ? C17C C17C S16C 114.2(5) 3_757 . ? C17C C17C H17E 108.7 3_757 . ? S16C C17C H17E 108.7 . . ? C17C C17C H17F 108.7 3_757 . ? S16C C17C H17F 108.7 . . ? H17E C17C H17F 107.6 . . ? C8C N9D C10D 122.7(15) . . ? C11D C10D C15D 120.0 . . ? C11D C10D N9D 120.8(8) . . ? C15D C10D N9D 119.2(8) . . ? C10D C11D C12D 120.0 . . ? C10D C11D H11D 120.0 . . ? C12D C11D H11D 120.0 . . ? C13D C12D C11D 120.0 . . ? C13D C12D H12D 120.0 . . ? C11D C12D H12D 120.0 . . ? C14D C13D C12D 120.0 . . ? C14D C13D H13D 120.0 . . ? C12D C13D H13D 120.0 . . ? C15D C14D C13D 120.0 . . ? C15D C14D H14D 120.0 . . ? C13D C14D H14D 120.0 . . ? C14D C15D C10D 120.0 . . ? C14D C15D S16D 121.5(3) . . ? C10D C15D S16D 118.5(3) . . ? C15D S16D C17D 105.1(10) . . ? C17D C17D S16D 106.9(14) 3_757 . ? C17D C17D H17G 110.3 3_757 . ? S16D C17D H17G 110.3 . . ? C17D C17D H17H 110.3 3_757 . ? S16D C17D H17H 110.3 . . ? H17G C17D H17H 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C2A C3A C4A 179.0(3) . . . . ? C7A C2A C3A C4A -1.7(5) . . . . ? C2A C3A C4A C5A 0.7(5) . . . . ? C3A C4A C5A C6A 0.8(5) . . . . ? C4A C5A C6A C7A -1.4(5) . . . . ? C5A C6A C7A C2A 0.5(5) . . . . ? C5A C6A C7A C8A 178.9(3) . . . . ? O1A C2A C7A C6A -179.6(3) . . . . ? C3A C2A C7A C6A 1.1(4) . . . . ? O1A C2A C7A C8A 2.0(5) . . . . ? C3A C2A C7A C8A -177.3(3) . . . . ? C6A C7A C8A N9B -176.3(8) . . . . ? C2A C7A C8A N9B 2.1(9) . . . . ? C6A C7A C8A N9A -178.5(3) . . . . ? C2A C7A C8A N9A -0.1(5) . . . . ? N9B C8A N9A C10A 166(6) . . . . ? C7A C8A N9A C10A 179.8(2) . . . . ? C8A N9A C10A C11A 17.5(4) . . . . ? C8A N9A C10A C15A -162.5(4) . . . . ? C15A C10A C11A C12A 0.0 . . . . ? N9A C10A C11A C12A 180.0 . . . . ? C10A C11A C12A C13A 0.0 . . . . ? C11A C12A C13A C14A 0.0 . . . . ? C12A C13A C14A C15A 0.0 . . . . ? C13A C14A C15A C10A 0.0 . . . . ? C13A C14A C15A S16A 180.0 . . . . ? C11A C10A C15A C14A 0.0 . . . . ? N9A C10A C15A C14A -180.0 . . . . ? C11A C10A C15A S16A -180.0 . . . . ? N9A C10A C15A S16A 0.04(3) . . . . ? C14A C15A S16A C17A 8.29(18) . . . . ? C10A C15A S16A C17A -171.74(18) . . . . ? C15A S16A C17A C17A 78.3(4) . . . 3_657 ? N9A C8A N9B C10B -12(5) . . . . ? C7A C8A N9B C10B -179.2(4) . . . . ? C8A N9B C10B C11B 5.6(11) . . . . ? C8A N9B C10B C15B -174.4(11) . . . . ? C15B C10B C11B C12B 0.0 . . . . ? N9B C10B C11B C12B 180.0 . . . . ? C10B C11B C12B C13B 0.0 . . . . ? C11B C12B C13B C14B 0.0 . . . . ? C12B C13B C14B C15B 0.0 . . . . ? C13B C14B C15B C10B 0.0 . . . . ? C13B C14B C15B S16B 180.0 . . . . ? C11B C10B C15B C14B 0.0 . . . . ? N9B C10B C15B C14B 180.0 . . . . ? C11B C10B C15B S16B -180.0 . . . . ? N9B C10B C15B S16B 0.01(3) . . . . ? C14B C15B S16B C17B -7.7(6) . . . . ? C10B C15B S16B C17B 172.3(6) . . . . ? C15B S16B C17B C17B 64(2) . . . 3_657 ? O1C C2C C3C C4C 178.9(3) . . . . ? C7C C2C C3C C4C -1.4(5) . . . . ? C2C C3C C4C C5C 1.4(5) . . . . ? C3C C4C C5C C6C -1.1(5) . . . . ? C4C C5C C6C C7C 0.8(5) . . . . ? C5C C6C C7C C2C -0.7(4) . . . . ? C5C C6C C7C C8C 177.9(3) . . . . ? O1C C2C C7C C6C -179.3(3) . . . . ? C3C C2C C7C C6C 1.0(4) . . . . ? O1C C2C C7C C8C 2.1(5) . . . . ? C3C C2C C7C C8C -177.5(3) . . . . ? C6C C7C C8C N9D -178.1(8) . . . . ? C2C C7C C8C N9D 0.4(8) . . . . ? C6C C7C C8C N9C -171.9(3) . . . . ? C2C C7C C8C N9C 6.6(5) . . . . ? N9D C8C N9C C10C -70(10) . . . . ? C7C C8C N9C C10C -179.4(2) . . . . ? C8C N9C C10C C11C -18.6(4) . . . . ? C8C N9C C10C C15C 161.4(4) . . . . ? C15C C10C C11C C12C 0.0 . . . . ? N9C C10C C11C C12C 180.0 . . . . ? C10C C11C C12C C13C 0.0 . . . . ? C11C C12C C13C C14C 0.0 . . . . ? C12C C13C C14C C15C 0.0 . . . . ? C13C C14C C15C C10C 0.0 . . . . ? C13C C14C C15C S16C 179.9 . . . . ? C11C C10C C15C C14C 0.0 . . . . ? N9C C10C C15C C14C -180.0 . . . . ? C11C C10C C15C S16C -180.0 . . . . ? N9C C10C C15C S16C 0.06(3) . . . . ? C14C C15C S16C C17C 6.5(2) . . . . ? C10C C15C S16C C17C -173.5(2) . . . . ? C15C S16C C17C C17C -79.3(10) . . . 3_757 ? N9C C8C N9D C10D 104(11) . . . . ? C7C C8C N9D C10D 177.8(4) . . . . ? C8C N9D C10D C11D -0.8(11) . . . . ? C8C N9D C10D C15D 179.2(11) . . . . ? C15D C10D C11D C12D 0.0 . . . . ? N9D C10D C11D C12D 180.0 . . . . ? C10D C11D C12D C13D 0.0 . . . . ? C11D C12D C13D C14D 0.0 . . . . ? C12D C13D C14D C15D 0.0 . . . . ? C13D C14D C15D C10D 0.0 . . . . ? C13D C14D C15D S16D 180.0 . . . . ? C11D C10D C15D C14D 0.0 . . . . ? N9D C10D C15D C14D 180.0 . . . . ? C11D C10D C15D S16D -180.0 . . . . ? N9D C10D C15D S16D 0.02(3) . . . . ? C14D C15D S16D C17D 28.6(6) . . . . ? C10D C15D S16D C17D -151.4(6) . . . . ? C15D S16D C17D C17D -100(3) . . . 3_757 ? 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 O1A H1A N9B 0.84 1.78 2.505(17) 143.8 . O1A H1A N9A 0.84 1.94 2.680(5) 146.7 . O1A H1A S16B 0.84 2.75 3.459(6) 142.8 . O1A H1A S16A 0.84 2.97 3.666(3) 141.9 . O1C H1C N9C 0.84 1.90 2.644(6) 146.8 . O1C H1C N9D 0.84 1.94 2.668(16) 144.1 . O1C H1C S16C 0.84 2.86 3.573(3) 143.8 . O1C H1C S16D 0.84 2.95 3.668(5) 144.8 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.805 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.072 data_cpr105 _database_code_CSD 172100 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H21 Co N2 O2 S2' _chemical_formula_weight 540.52 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' Co Co 0.3494 0.9721 '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 monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.279(1) _cell_length_b 12.807(1) _cell_length_c 12.191(1) _cell_angle_alpha 90.00 _cell_angle_beta 94.51(1) _cell_angle_gamma 90.00 _cell_volume 2378.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6099 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'dark grey' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type 'empirical from multiple relf.' _exptl_absorpt_correction_T_min 0.8803 _exptl_absorpt_correction_T_max 0.9088 _exptl_absorpt_process_details 'MULABS (Platon2000; cf. Blessing 1995)' _exptl_special_details ; dx = 30 mm; 180 sec./deg., 1 deg., 181 frames; mos. = 0.418(2) deg. ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6743 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3542 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L.Spek, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0000P)^2^+1.1228P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(12) _refine_ls_number_reflns 3542 _refine_ls_number_parameters 316 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0636 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.29376(3) 0.76489(3) 0.24391(3) 0.01768(11) Uani 1 1 d . . . O1A O 0.20263(14) 0.72390(16) 0.33411(16) 0.0225(5) Uani 1 1 d . . . C2A C 0.2030(2) 0.7487(2) 0.4386(3) 0.0192(7) Uani 1 1 d . . . C3A C 0.1449(2) 0.6964(2) 0.5039(3) 0.0252(7) Uani 1 1 d . . . H3A H 0.1057 0.6459 0.4706 0.030 Uiso 1 1 calc R . . C4A C 0.1434(2) 0.7162(3) 0.6139(3) 0.0291(8) Uani 1 1 d . . . H4A H 0.1031 0.6799 0.6555 0.035 Uiso 1 1 calc R . . C5A C 0.2009(2) 0.7901(3) 0.6662(3) 0.0280(8) Uani 1 1 d . . . H5A H 0.2015 0.8018 0.7432 0.034 Uiso 1 1 calc R . . C6A C 0.2555(2) 0.8441(2) 0.6045(2) 0.0241(7) Uani 1 1 d . . . H6A H 0.2930 0.8954 0.6393 0.029 Uiso 1 1 calc R . . C7A C 0.2586(2) 0.8267(2) 0.4903(2) 0.0202(7) Uani 1 1 d . . . C8A C 0.3153(2) 0.8914(2) 0.4326(2) 0.0217(7) Uani 1 1 d . . . H8A H 0.3455 0.9451 0.4739 0.026 Uiso 1 1 calc R . . N9A N 0.33017(17) 0.8848(2) 0.3292(2) 0.0200(6) Uani 1 1 d . . . C10A C 0.38704(18) 0.9587(2) 0.2830(2) 0.0172(6) Uani 1 1 d . . . C11A C 0.4072(2) 1.0572(2) 0.3273(3) 0.0224(7) Uani 1 1 d . . . H11A H 0.3814 1.0795 0.3917 0.027 Uiso 1 1 calc R . . C12A C 0.4645(2) 1.1222(3) 0.2777(3) 0.0277(8) Uani 1 1 d . . . H12A H 0.4792 1.1884 0.3092 0.033 Uiso 1 1 calc R . . C13A C 0.5005(2) 1.0916(3) 0.1827(3) 0.0271(8) Uani 1 1 d . . . H13A H 0.5396 1.1369 0.1489 0.032 Uiso 1 1 calc R . . C14A C 0.4801(2) 0.9954(2) 0.1363(3) 0.0220(7) Uani 1 1 d . . . H14A H 0.5053 0.9749 0.0708 0.026 Uiso 1 1 calc R . . C15A C 0.42216(19) 0.9276(2) 0.1853(2) 0.0180(7) Uani 1 1 d . . . S16A S 0.39508(5) 0.80578(6) 0.12802(6) 0.02089(18) Uani 1 1 d . . . O1B O 0.37378(14) 0.69108(15) 0.34196(17) 0.0224(5) Uani 1 1 d . . . C2B C 0.3726(2) 0.5904(2) 0.3566(3) 0.0204(7) Uani 1 1 d . . . C3B C 0.4144(2) 0.5496(3) 0.4553(3) 0.0269(8) Uani 1 1 d . . . H3B H 0.4384 0.5959 0.5107 0.032 Uiso 1 1 calc R . . C4B C 0.4205(2) 0.4433(3) 0.4719(3) 0.0298(8) Uani 1 1 d . . . H4B H 0.4497 0.4175 0.5381 0.036 Uiso 1 1 calc R . . C5B C 0.3851(2) 0.3731(3) 0.3939(3) 0.0305(8) Uani 1 1 d . . . H5B H 0.3908 0.3001 0.4063 0.037 Uiso 1 1 calc R . . C6B C 0.3417(2) 0.4096(3) 0.2991(3) 0.0271(8) Uani 1 1 d . . . H6B H 0.3175 0.3615 0.2457 0.033 Uiso 1 1 calc R . . C7B C 0.3326(2) 0.5191(2) 0.2796(3) 0.0219(7) Uani 1 1 d . . . C8B C 0.2810(2) 0.5501(2) 0.1828(3) 0.0200(7) Uani 1 1 d . . . H8B H 0.2598 0.4962 0.1343 0.024 Uiso 1 1 calc R . . N9B N 0.26019(17) 0.6454(2) 0.15432(19) 0.0183(6) Uani 1 1 d . . . C10B C 0.20178(19) 0.6631(2) 0.0573(2) 0.0178(7) Uani 1 1 d . . . C11B C 0.1771(2) 0.5871(3) -0.0209(3) 0.0263(7) Uani 1 1 d . . . H11B H 0.2045 0.5206 -0.0166 0.032 Uiso 1 1 calc R . . C12B C 0.1136(2) 0.6073(3) -0.1043(3) 0.0267(8) Uani 1 1 d . . . H12B H 0.0961 0.5537 -0.1552 0.032 Uiso 1 1 calc R . . C13B C 0.0746(2) 0.7048(3) -0.1153(3) 0.0273(8) Uani 1 1 d . . . H13B H 0.0289 0.7172 -0.1711 0.033 Uiso 1 1 calc R . . C14B C 0.1034(2) 0.7845(3) -0.0433(3) 0.0246(8) Uani 1 1 d . . . H14B H 0.0804 0.8531 -0.0528 0.030 Uiso 1 1 calc R . . C15B C 0.1661(2) 0.7626(2) 0.0424(2) 0.0201(7) Uani 1 1 d . . . S16B S 0.20200(5) 0.86252(6) 0.13628(6) 0.02019(18) Uani 1 1 d . . . C17B C 0.1050(2) 0.8821(3) 0.2056(3) 0.0260(7) Uani 1 1 d . . . H17B H 0.0758 0.8238 0.2343 0.031 Uiso 1 1 calc R . . C18B C 0.0738(2) 0.9757(3) 0.2175(4) 0.0445(10) Uani 1 1 d . . . H18A H 0.1028 1.0342 0.1890 0.053 Uiso 1 1 calc R . . H18B H 0.0221 0.9854 0.2546 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0188(2) 0.0172(2) 0.0168(2) -0.0016(2) -0.00089(14) -0.00274(19) O1A 0.0275(13) 0.0246(12) 0.0155(11) -0.0047(10) 0.0011(9) -0.0025(10) C2A 0.0195(17) 0.0187(15) 0.0193(16) 0.0017(13) 0.0006(12) 0.0017(12) C3A 0.0262(19) 0.0233(17) 0.0256(17) 0.0020(15) -0.0004(14) -0.0039(14) C4A 0.030(2) 0.0303(18) 0.0276(18) 0.0032(15) 0.0070(15) -0.0036(15) C5A 0.037(2) 0.0305(18) 0.0171(16) -0.0015(15) 0.0041(14) -0.0017(15) C6A 0.032(2) 0.0203(16) 0.0201(17) 0.0007(14) -0.0001(14) -0.0024(14) C7A 0.0249(17) 0.0183(15) 0.0176(15) 0.0006(14) 0.0035(13) -0.0013(13) C8A 0.0270(19) 0.0199(16) 0.0179(16) -0.0036(14) -0.0005(13) -0.0039(13) N9A 0.0200(15) 0.0193(13) 0.0210(14) 0.0021(12) 0.0033(11) -0.0012(11) C10A 0.0144(16) 0.0156(14) 0.0215(17) 0.0038(13) 0.0013(12) -0.0011(12) C11A 0.0244(18) 0.0219(16) 0.0208(16) 0.0001(14) 0.0008(13) 0.0012(13) C12A 0.033(2) 0.0173(16) 0.032(2) -0.0045(15) -0.0012(15) -0.0059(14) C13A 0.0235(18) 0.0224(17) 0.036(2) 0.0052(16) 0.0069(14) -0.0075(14) C14A 0.0178(16) 0.0264(17) 0.0222(16) 0.0025(14) 0.0038(12) 0.0030(13) C15A 0.0173(17) 0.0163(16) 0.0198(16) 0.0005(13) -0.0022(12) 0.0023(12) S16A 0.0212(4) 0.0204(4) 0.0214(4) -0.0024(4) 0.0038(3) -0.0035(3) O1B 0.0251(13) 0.0174(11) 0.0240(12) -0.0009(10) -0.0030(9) -0.0036(9) C2B 0.0200(17) 0.0207(16) 0.0211(16) 0.0018(14) 0.0047(12) -0.0025(13) C3B 0.0270(19) 0.0298(19) 0.0233(17) 0.0048(15) -0.0014(14) -0.0050(14) C4B 0.0285(19) 0.0319(19) 0.0286(18) 0.0080(16) -0.0008(15) 0.0033(15) C5B 0.037(2) 0.0203(17) 0.034(2) 0.0067(16) 0.0045(16) 0.0057(14) C6B 0.032(2) 0.0207(16) 0.0285(18) -0.0021(15) 0.0039(15) -0.0034(14) C7B 0.0244(18) 0.0201(16) 0.0216(17) -0.0005(14) 0.0035(13) -0.0005(13) C8B 0.0229(18) 0.0190(17) 0.0186(16) -0.0031(14) 0.0037(13) -0.0024(13) N9B 0.0176(15) 0.0224(14) 0.0146(13) -0.0020(11) -0.0010(10) -0.0044(11) C10B 0.0169(16) 0.0237(18) 0.0130(15) -0.0016(13) 0.0026(12) -0.0041(13) C11B 0.0292(19) 0.0271(18) 0.0224(17) -0.0028(15) 0.0009(14) -0.0047(14) C12B 0.0257(19) 0.0339(19) 0.0205(17) -0.0062(15) 0.0014(14) -0.0097(15) C13B 0.0199(18) 0.043(2) 0.0179(17) -0.0021(16) -0.0027(13) -0.0031(15) C14B 0.0221(18) 0.0321(19) 0.0199(18) 0.0052(16) 0.0030(13) 0.0016(14) C15B 0.0178(18) 0.0257(18) 0.0175(16) -0.0014(14) 0.0048(13) -0.0087(14) S16B 0.0199(4) 0.0205(4) 0.0201(4) -0.0007(3) 0.0005(3) -0.0006(3) C17B 0.0205(18) 0.0311(18) 0.0264(18) -0.0006(15) 0.0010(13) -0.0021(14) C18B 0.029(2) 0.038(2) 0.068(3) -0.013(2) 0.0129(19) 0.0026(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 Co1 O1B 1.894(2) . ? Co1 N9A 1.913(3) . ? Co1 O1A 1.914(2) . ? Co1 N9B 1.926(2) . ? Co1 S16B 2.2274(9) . ? Co1 S16A 2.2384(9) . ? O1A C2A 1.312(4) . ? C2A C3A 1.408(5) . ? C2A C7A 1.426(4) . ? C3A C4A 1.367(5) . ? C3A H3A 0.9500 . ? C4A C5A 1.410(5) . ? C4A H4A 0.9500 . ? C5A C6A 1.355(4) . ? C5A H5A 0.9500 . ? C6A C7A 1.414(4) . ? C6A H6A 0.9500 . ? C7A C8A 1.425(4) . ? C8A N9A 1.300(4) . ? C8A H8A 0.9500 . ? N9A C10A 1.431(4) . ? C10A C11A 1.397(4) . ? C10A C15A 1.402(4) . ? C11A C12A 1.382(4) . ? C11A H11A 0.9500 . ? C12A C13A 1.378(4) . ? C12A H12A 0.9500 . ? C13A C14A 1.381(5) . ? C13A H13A 0.9500 . ? C14A C15A 1.407(4) . ? C14A H14A 0.9500 . ? C15A S16A 1.745(3) . ? O1B C2B 1.301(4) . ? C2B C7B 1.415(4) . ? C2B C3B 1.417(4) . ? C3B C4B 1.379(5) . ? C3B H3B 0.9500 . ? C4B C5B 1.387(5) . ? C4B H4B 0.9500 . ? C5B C6B 1.369(5) . ? C5B H5B 0.9500 . ? C6B C7B 1.428(4) . ? C6B H6B 0.9500 . ? C7B C8B 1.423(4) . ? C8B N9B 1.301(4) . ? C8B H8B 0.9500 . ? N9B C10B 1.442(4) . ? C10B C15B 1.392(4) . ? C10B C11B 1.394(4) . ? C11B C12B 1.373(5) . ? C11B H11B 0.9500 . ? C12B C13B 1.385(5) . ? C12B H12B 0.9500 . ? C13B C14B 1.394(5) . ? C13B H13B 0.9500 . ? C14B C15B 1.390(4) . ? C14B H14B 0.9500 . ? C15B S16B 1.775(3) . ? S16B C17B 1.780(3) . ? C17B C18B 1.302(5) . ? C17B H17B 0.9500 . ? C18B H18A 0.9500 . ? C18B H18B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1B Co1 N9A 84.93(10) . . ? O1B Co1 O1A 87.89(9) . . ? N9A Co1 O1A 95.81(10) . . ? O1B Co1 N9B 95.23(10) . . ? N9A Co1 N9B 177.94(12) . . ? O1A Co1 N9B 86.25(10) . . ? O1B Co1 S16B 175.64(7) . . ? N9A Co1 S16B 90.72(8) . . ? O1A Co1 S16B 92.28(7) . . ? N9B Co1 S16B 89.13(8) . . ? O1B Co1 S16A 94.07(7) . . ? N9A Co1 S16A 88.25(8) . . ? O1A Co1 S16A 175.64(7) . . ? N9B Co1 S16A 89.69(8) . . ? S16B Co1 S16A 86.07(3) . . ? C2A O1A Co1 122.92(19) . . ? O1A C2A C3A 118.6(3) . . ? O1A C2A C7A 123.8(3) . . ? C3A C2A C7A 117.6(3) . . ? C4A C3A C2A 121.7(3) . . ? C4A C3A H3A 119.1 . . ? C2A C3A H3A 119.1 . . ? C3A C4A C5A 120.7(3) . . ? C3A C4A H4A 119.6 . . ? C5A C4A H4A 119.6 . . ? C6A C5A C4A 118.7(3) . . ? C6A C5A H5A 120.7 . . ? C4A C5A H5A 120.7 . . ? C5A C6A C7A 122.4(3) . . ? C5A C6A H6A 118.8 . . ? C7A C6A H6A 118.8 . . ? C6A C7A C8A 117.6(3) . . ? C6A C7A C2A 118.7(3) . . ? C8A C7A C2A 123.6(3) . . ? N9A C8A C7A 126.8(3) . . ? N9A C8A H8A 116.6 . . ? C7A C8A H8A 116.6 . . ? C8A N9A C10A 119.7(3) . . ? C8A N9A Co1 121.0(2) . . ? C10A N9A Co1 118.48(19) . . ? C11A C10A C15A 119.9(3) . . ? C11A C10A N9A 124.6(3) . . ? C15A C10A N9A 115.5(2) . . ? C12A C11A C10A 120.2(3) . . ? C12A C11A H11A 119.9 . . ? C10A C11A H11A 119.9 . . ? C13A C12A C11A 120.3(3) . . ? C13A C12A H12A 119.8 . . ? C11A C12A H12A 119.8 . . ? C12A C13A C14A 120.4(3) . . ? C12A C13A H13A 119.8 . . ? C14A C13A H13A 119.8 . . ? C13A C14A C15A 120.4(3) . . ? C13A C14A H14A 119.8 . . ? C15A C14A H14A 119.8 . . ? C10A C15A C14A 118.7(3) . . ? C10A C15A S16A 120.0(2) . . ? C14A C15A S16A 121.3(2) . . ? C15A S16A Co1 96.35(10) . . ? C2B O1B Co1 124.5(2) . . ? O1B C2B C7B 123.9(3) . . ? O1B C2B C3B 118.2(3) . . ? C7B C2B C3B 117.9(3) . . ? C4B C3B C2B 120.6(3) . . ? C4B C3B H3B 119.7 . . ? C2B C3B H3B 119.7 . . ? C3B C4B C5B 121.5(3) . . ? C3B C4B H4B 119.3 . . ? C5B C4B H4B 119.3 . . ? C6B C5B C4B 119.6(3) . . ? C6B C5B H5B 120.2 . . ? C4B C5B H5B 120.2 . . ? C5B C6B C7B 120.7(3) . . ? C5B C6B H6B 119.7 . . ? C7B C6B H6B 119.7 . . ? C2B C7B C8B 123.5(3) . . ? C2B C7B C6B 119.5(3) . . ? C8B C7B C6B 116.9(3) . . ? N9B C8B C7B 126.2(3) . . ? N9B C8B H8B 116.9 . . ? C7B C8B H8B 116.9 . . ? C8B N9B C10B 119.2(3) . . ? C8B N9B Co1 123.0(2) . . ? C10B N9B Co1 117.4(2) . . ? C15B C10B C11B 117.9(3) . . ? C15B C10B N9B 117.5(3) . . ? C11B C10B N9B 124.6(3) . . ? C12B C11B C10B 120.8(3) . . ? C12B C11B H11B 119.6 . . ? C10B C11B H11B 119.6 . . ? C11B C12B C13B 121.0(3) . . ? C11B C12B H12B 119.5 . . ? C13B C12B H12B 119.5 . . ? C12B C13B C14B 119.1(3) . . ? C12B C13B H13B 120.4 . . ? C14B C13B H13B 120.4 . . ? C15B C14B C13B 119.3(3) . . ? C15B C14B H14B 120.3 . . ? C13B C14B H14B 120.3 . . ? C14B C15B C10B 121.5(3) . . ? C14B C15B S16B 119.9(3) . . ? C10B C15B S16B 118.5(2) . . ? C15B S16B C17B 100.48(15) . . ? C15B S16B Co1 97.08(11) . . ? C17B S16B Co1 107.94(11) . . ? C18B C17B S16B 120.5(3) . . ? C18B C17B H17B 119.7 . . ? S16B C17B H17B 119.7 . . ? C17B C18B H18A 120.0 . . ? C17B C18B H18B 120.0 . . ? H18A C18B H18B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1B Co1 O1A C2A 59.6(2) . . . . ? N9A Co1 O1A C2A -25.1(2) . . . . ? N9B Co1 O1A C2A 155.0(2) . . . . ? S16B Co1 O1A C2A -116.1(2) . . . . ? S16A Co1 O1A C2A 176.3(8) . . . . ? Co1 O1A C2A C3A -165.9(2) . . . . ? Co1 O1A C2A C7A 14.6(4) . . . . ? O1A C2A C3A C4A 178.2(3) . . . . ? C7A C2A C3A C4A -2.3(5) . . . . ? C2A C3A C4A C5A -0.4(5) . . . . ? C3A C4A C5A C6A 2.5(5) . . . . ? C4A C5A C6A C7A -1.9(5) . . . . ? C5A C6A C7A C8A 177.0(3) . . . . ? C5A C6A C7A C2A -0.8(5) . . . . ? O1A C2A C7A C6A -177.7(3) . . . . ? C3A C2A C7A C6A 2.8(4) . . . . ? O1A C2A C7A C8A 4.7(5) . . . . ? C3A C2A C7A C8A -174.8(3) . . . . ? C6A C7A C8A N9A 176.8(3) . . . . ? C2A C7A C8A N9A -5.6(5) . . . . ? C7A C8A N9A C10A 177.8(3) . . . . ? C7A C8A N9A Co1 -12.9(4) . . . . ? O1B Co1 N9A C8A -63.6(2) . . . . ? O1A Co1 N9A C8A 23.8(3) . . . . ? N9B Co1 N9A C8A -158(3) . . . . ? S16B Co1 N9A C8A 116.1(2) . . . . ? S16A Co1 N9A C8A -157.8(2) . . . . ? O1B Co1 N9A C10A 105.9(2) . . . . ? O1A Co1 N9A C10A -166.8(2) . . . . ? N9B Co1 N9A C10A 11(3) . . . . ? S16B Co1 N9A C10A -74.4(2) . . . . ? S16A Co1 N9A C10A 11.6(2) . . . . ? C8A N9A C10A C11A -21.4(4) . . . . ? Co1 N9A C10A C11A 169.0(2) . . . . ? C8A N9A C10A C15A 159.8(3) . . . . ? Co1 N9A C10A C15A -9.8(3) . . . . ? C15A C10A C11A C12A -2.7(4) . . . . ? N9A C10A C11A C12A 178.6(3) . . . . ? C10A C11A C12A C13A 1.6(5) . . . . ? C11A C12A C13A C14A -0.3(5) . . . . ? C12A C13A C14A C15A 0.1(5) . . . . ? C11A C10A C15A C14A 2.5(4) . . . . ? N9A C10A C15A C14A -178.7(3) . . . . ? C11A C10A C15A S16A -178.5(2) . . . . ? N9A C10A C15A S16A 0.3(4) . . . . ? C13A C14A C15A C10A -1.2(4) . . . . ? C13A C14A C15A S16A 179.8(2) . . . . ? C10A C15A S16A Co1 7.0(2) . . . . ? C14A C15A S16A Co1 -174.0(2) . . . . ? O1B Co1 S16A C15A -93.74(12) . . . . ? N9A Co1 S16A C15A -8.96(12) . . . . ? O1A Co1 S16A C15A 149.7(9) . . . . ? N9B Co1 S16A C15A 171.03(13) . . . . ? S16B Co1 S16A C15A 81.89(10) . . . . ? N9A Co1 O1B C2B 161.0(2) . . . . ? O1A Co1 O1B C2B 65.0(2) . . . . ? N9B Co1 O1B C2B -21.0(2) . . . . ? S16B Co1 O1B C2B 157.3(8) . . . . ? S16A Co1 O1B C2B -111.1(2) . . . . ? Co1 O1B C2B C7B 21.5(4) . . . . ? Co1 O1B C2B C3B -158.9(2) . . . . ? O1B C2B C3B C4B -175.5(3) . . . . ? C7B C2B C3B C4B 4.1(5) . . . . ? C2B C3B C4B C5B -1.1(5) . . . . ? C3B C4B C5B C6B -1.0(5) . . . . ? C4B C5B C6B C7B -0.1(5) . . . . ? O1B C2B C7B C8B -7.0(5) . . . . ? C3B C2B C7B C8B 173.4(3) . . . . ? O1B C2B C7B C6B 174.4(3) . . . . ? C3B C2B C7B C6B -5.1(4) . . . . ? C5B C6B C7B C2B 3.2(5) . . . . ? C5B C6B C7B C8B -175.4(3) . . . . ? C2B C7B C8B N9B -3.4(5) . . . . ? C6B C7B C8B N9B 175.2(3) . . . . ? C7B C8B N9B C10B -175.4(3) . . . . ? C7B C8B N9B Co1 -2.1(5) . . . . ? O1B Co1 N9B C8B 11.4(3) . . . . ? N9A Co1 N9B C8B 106(3) . . . . ? O1A Co1 N9B C8B -76.1(3) . . . . ? S16B Co1 N9B C8B -168.4(2) . . . . ? S16A Co1 N9B C8B 105.5(2) . . . . ? O1B Co1 N9B C10B -175.1(2) . . . . ? N9A Co1 N9B C10B -81(3) . . . . ? O1A Co1 N9B C10B 97.3(2) . . . . ? S16B Co1 N9B C10B 5.0(2) . . . . ? S16A Co1 N9B C10B -81.1(2) . . . . ? C8B N9B C10B C15B 166.5(3) . . . . ? Co1 N9B C10B C15B -7.2(3) . . . . ? C8B N9B C10B C11B -12.0(4) . . . . ? Co1 N9B C10B C11B 174.3(2) . . . . ? C15B C10B C11B C12B -5.9(4) . . . . ? N9B C10B C11B C12B 172.6(3) . . . . ? C10B C11B C12B C13B 2.4(5) . . . . ? C11B C12B C13B C14B 2.9(5) . . . . ? C12B C13B C14B C15B -4.4(5) . . . . ? C13B C14B C15B C10B 0.8(5) . . . . ? C13B C14B C15B S16B -178.8(2) . . . . ? C11B C10B C15B C14B 4.3(4) . . . . ? N9B C10B C15B C14B -174.3(3) . . . . ? C11B C10B C15B S16B -176.1(2) . . . . ? N9B C10B C15B S16B 5.3(4) . . . . ? C14B C15B S16B C17B 68.5(3) . . . . ? C10B C15B S16B C17B -111.1(3) . . . . ? C14B C15B S16B Co1 178.3(2) . . . . ? C10B C15B S16B Co1 -1.3(3) . . . . ? O1B Co1 S16B C15B 180(100) . . . . ? N9A Co1 S16B C15B 176.10(13) . . . . ? O1A Co1 S16B C15B -88.05(12) . . . . ? N9B Co1 S16B C15B -1.84(12) . . . . ? S16A Co1 S16B C15B 87.90(10) . . . . ? O1B Co1 S16B C17B -76.7(10) . . . . ? N9A Co1 S16B C17B -80.44(14) . . . . ? O1A Co1 S16B C17B 15.41(13) . . . . ? N9B Co1 S16B C17B 101.62(14) . . . . ? S16A Co1 S16B C17B -168.64(12) . . . . ? C15B S16B C17B C18B -130.1(3) . . . . ? Co1 S16B C17B C18B 128.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.263 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.051 data_cpr097 _database_code_CSD 195200 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N2 O2 S2 Zn' _chemical_formula_weight 547.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 tetragonal _symmetry_space_group_name_H-M P4(1) _symmetry_Int_Tables_number 76 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 11.383(1) _cell_length_b 11.383(1) _cell_length_c 18.347(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2377.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5931 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.239 _exptl_absorpt_correction_type 'empirical from multiple refl.' _exptl_absorpt_correction_T_min 0.8157 _exptl_absorpt_correction_T_max 0.8511 _exptl_absorpt_process_details 'MULABS (Platon2000; cf. Blessing 1995)' _exptl_special_details ; dx = 35 mm; 1 deg., 60 sec./deg., 150 frames; mos. = 0.384(2) deg. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8877 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3546 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Platon and Ortep3' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0197P)^2^+0.5432P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(12) _refine_ls_number_reflns 3546 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.30125(4) 0.22238(4) 0.23345(2) 0.02507(13) Uani 1 1 d . . . O1 O 0.4080(2) 0.2287(3) 0.14831(15) 0.0296(7) Uani 1 1 d . . . C2 C 0.5211(4) 0.2414(4) 0.1539(2) 0.0247(10) Uani 1 1 d . . . C3 C 0.5939(4) 0.2063(4) 0.0951(2) 0.0286(11) Uani 1 1 d . . . H3 H 0.5582 0.1732 0.0531 0.034 Uiso 1 1 calc R . . C4 C 0.7140(4) 0.2180(4) 0.0963(3) 0.0315(12) Uani 1 1 d . . . H4 H 0.7591 0.1923 0.0558 0.038 Uiso 1 1 calc R . . C5 C 0.7702(4) 0.2672(4) 0.1564(3) 0.0350(12) Uani 1 1 d . . . H5 H 0.8532 0.2756 0.1572 0.042 Uiso 1 1 calc R . . C6 C 0.7030(4) 0.3033(4) 0.2145(2) 0.0269(10) Uani 1 1 d . . . H6 H 0.7411 0.3370 0.2556 0.032 Uiso 1 1 calc R . . C7 C 0.5794(3) 0.2922(4) 0.2153(2) 0.0218(10) Uani 1 1 d . . . C8 C 0.5221(4) 0.3368(4) 0.2790(2) 0.0241(10) Uani 1 1 d . . . H8 H 0.5715 0.3712 0.3149 0.029 Uiso 1 1 calc R . . N9 N 0.4093(3) 0.3357(3) 0.29344(17) 0.0231(8) Uani 1 1 d . . . C10 C 0.3672(4) 0.3978(4) 0.3557(2) 0.0236(10) Uani 1 1 d . . . C11 C 0.4304(4) 0.4869(4) 0.3894(2) 0.0294(11) Uani 1 1 d . . . H11 H 0.5055 0.5074 0.3707 0.035 Uiso 1 1 calc R . . C12 C 0.3872(4) 0.5467(4) 0.4492(2) 0.0372(12) Uani 1 1 d . . . H12 H 0.4328 0.6067 0.4714 0.045 Uiso 1 1 calc R . . C13 C 0.2778(4) 0.5191(4) 0.4769(3) 0.0357(12) Uani 1 1 d . . . H13 H 0.2484 0.5586 0.5187 0.043 Uiso 1 1 calc R . . C14 C 0.2115(4) 0.4330(4) 0.4429(2) 0.0345(12) Uani 1 1 d . . . H14 H 0.1355 0.4146 0.4611 0.041 Uiso 1 1 calc R . . C15 C 0.2545(4) 0.3733(4) 0.3827(2) 0.0232(10) Uani 1 1 d . . . S16 S 0.16516(10) 0.26060(10) 0.34354(6) 0.0300(3) Uani 1 1 d . . . C17 C 0.0430(4) 0.3420(4) 0.3042(2) 0.0351(12) Uani 1 1 d . . . H17A H -0.0066 0.2866 0.2762 0.042 Uiso 1 1 calc R . . H17B H -0.0056 0.3737 0.3444 0.042 Uiso 1 1 calc R . . C18 C 0.0773(4) 0.4425(4) 0.2546(2) 0.0366(12) Uani 1 1 d . . . H18A H 0.1095 0.5065 0.2852 0.044 Uiso 1 1 calc R . . H18B H 0.0052 0.4727 0.2310 0.044 Uiso 1 1 calc R . . S19 S 0.18375(10) 0.40949(10) 0.18369(6) 0.0281(3) Uani 1 1 d . . . C20 C 0.1030(4) 0.3231(4) 0.1189(2) 0.0246(10) Uani 1 1 d . . . C21 C 0.0511(4) 0.3831(4) 0.0616(2) 0.0280(11) Uani 1 1 d . . . H21 H 0.0510 0.4666 0.0613 0.034 Uiso 1 1 calc R . . C22 C -0.0007(4) 0.3216(4) 0.0047(2) 0.0295(11) Uani 1 1 d . . . H22 H -0.0381 0.3623 -0.0341 0.035 Uiso 1 1 calc R . . C23 C 0.0028(4) 0.1991(4) 0.0052(2) 0.0327(11) Uani 1 1 d . . . H23 H -0.0301 0.1563 -0.0342 0.039 Uiso 1 1 calc R . . C24 C 0.0542(4) 0.1392(4) 0.0630(2) 0.0255(10) Uani 1 1 d . . . H24 H 0.0551 0.0557 0.0631 0.031 Uiso 1 1 calc R . . C25 C 0.1042(4) 0.2005(4) 0.1206(2) 0.0228(10) Uani 1 1 d . . . N26 N 0.1600(3) 0.1409(3) 0.17982(18) 0.0236(8) Uani 1 1 d . . . C27 C 0.1187(4) 0.0398(4) 0.2004(2) 0.0257(10) Uani 1 1 d . . . H27 H 0.0518 0.0120 0.1747 0.031 Uiso 1 1 calc R . . C28 C 0.1623(4) -0.0347(4) 0.2573(2) 0.0271(10) Uani 1 1 d . . . C29 C 0.0963(4) -0.1386(4) 0.2719(2) 0.0323(11) Uani 1 1 d . . . H29 H 0.0280 -0.1539 0.2437 0.039 Uiso 1 1 calc R . . C30 C 0.1276(5) -0.2164(4) 0.3246(3) 0.0409(13) Uani 1 1 d . . . H30 H 0.0818 -0.2847 0.3335 0.049 Uiso 1 1 calc R . . C31 C 0.2300(5) -0.1932(5) 0.3658(3) 0.0439(14) Uani 1 1 d . . . H31 H 0.2523 -0.2461 0.4035 0.053 Uiso 1 1 calc R . . C32 C 0.2971(5) -0.0967(4) 0.3526(2) 0.0393(12) Uani 1 1 d . . . H32 H 0.3649 -0.0834 0.3817 0.047 Uiso 1 1 calc R . . C33 C 0.2692(4) -0.0151(4) 0.2967(2) 0.0284(11) Uani 1 1 d . . . O34 O 0.3412(3) 0.0697(3) 0.28253(16) 0.0340(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0205(3) 0.0287(3) 0.0260(2) -0.0012(2) 0.0007(2) -0.0018(2) O1 0.0200(18) 0.042(2) 0.0262(15) -0.0049(14) -0.0003(13) -0.0027(14) C2 0.028(3) 0.021(2) 0.025(2) 0.0047(19) 0.003(2) 0.002(2) C3 0.035(3) 0.024(3) 0.026(2) 0.001(2) 0.004(2) -0.005(2) C4 0.029(3) 0.033(3) 0.033(3) 0.008(2) 0.009(2) 0.003(2) C5 0.024(3) 0.041(3) 0.040(3) 0.008(2) 0.004(2) -0.001(2) C6 0.027(3) 0.025(3) 0.028(2) 0.0060(19) -0.003(2) 0.000(2) C7 0.018(2) 0.021(2) 0.026(2) 0.0056(18) 0.0020(18) 0.0011(18) C8 0.027(3) 0.021(2) 0.024(2) 0.0050(19) -0.004(2) -0.0025(19) N9 0.021(2) 0.025(2) 0.0231(18) -0.0010(16) -0.0004(16) -0.0004(16) C10 0.022(2) 0.025(3) 0.023(2) 0.0014(19) 0.0002(19) 0.002(2) C11 0.019(2) 0.034(3) 0.036(3) -0.005(2) -0.004(2) -0.002(2) C12 0.035(3) 0.039(3) 0.037(3) -0.016(2) -0.009(2) 0.006(2) C13 0.038(3) 0.042(3) 0.027(2) -0.006(2) -0.004(2) 0.008(2) C14 0.035(3) 0.040(3) 0.028(2) 0.001(2) 0.006(2) 0.003(2) C15 0.025(3) 0.023(3) 0.021(2) 0.0015(19) -0.0005(19) 0.0019(19) S16 0.0305(7) 0.0295(7) 0.0300(6) -0.0010(5) 0.0073(5) -0.0040(6) C17 0.026(3) 0.042(3) 0.037(3) -0.008(2) 0.001(2) 0.003(2) C18 0.038(3) 0.035(3) 0.037(3) -0.005(2) 0.002(2) 0.008(2) S19 0.0281(7) 0.0247(6) 0.0315(6) 0.0016(5) -0.0003(5) -0.0030(5) C20 0.021(3) 0.028(3) 0.025(2) 0.002(2) 0.0052(19) 0.000(2) C21 0.022(3) 0.031(3) 0.031(2) 0.009(2) 0.006(2) 0.004(2) C22 0.025(3) 0.033(3) 0.030(2) 0.005(2) -0.004(2) 0.006(2) C23 0.023(3) 0.047(3) 0.028(2) -0.004(2) -0.002(2) -0.005(2) C24 0.023(3) 0.023(3) 0.031(2) -0.003(2) -0.001(2) -0.001(2) C25 0.019(2) 0.023(3) 0.027(2) 0.003(2) 0.0055(19) 0.0004(19) N26 0.022(2) 0.024(2) 0.0251(18) 0.0027(16) 0.0013(16) 0.0029(17) C27 0.024(3) 0.023(3) 0.030(2) -0.003(2) 0.0013(19) -0.003(2) C28 0.030(3) 0.026(3) 0.026(2) 0.002(2) 0.003(2) 0.004(2) C29 0.036(3) 0.023(3) 0.037(3) -0.002(2) 0.002(2) -0.005(2) C30 0.057(4) 0.024(3) 0.043(3) 0.006(2) 0.010(3) 0.000(3) C31 0.057(4) 0.040(3) 0.034(3) 0.013(2) 0.006(3) 0.014(3) C32 0.040(3) 0.039(3) 0.039(3) 0.010(2) 0.004(2) 0.007(2) C33 0.029(3) 0.024(3) 0.032(3) -0.001(2) 0.008(2) 0.003(2) O34 0.0243(18) 0.037(2) 0.0401(18) 0.0050(16) -0.0061(15) 0.0019(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.980(3) . ? Zn1 O34 2.009(3) . ? Zn1 N9 2.095(3) . ? Zn1 N26 2.101(4) . ? Zn1 S16 2.5824(11) . ? Zn1 S19 2.6755(13) . ? O1 C2 1.300(5) . ? C2 C3 1.418(6) . ? C2 C7 1.429(6) . ? C3 C4 1.373(6) . ? C3 H3 0.9500 . ? C4 C5 1.392(7) . ? C4 H4 0.9500 . ? C5 C6 1.375(6) . ? C5 H5 0.9500 . ? C6 C7 1.414(6) . ? C6 H6 0.9500 . ? C7 C8 1.432(5) . ? C8 N9 1.311(5) . ? C8 H8 0.9500 . ? N9 C10 1.427(5) . ? C10 C11 1.389(6) . ? C10 C15 1.403(6) . ? C11 C12 1.382(6) . ? C11 H11 0.9500 . ? C12 C13 1.381(7) . ? C12 H12 0.9500 . ? C13 C14 1.385(6) . ? C13 H13 0.9500 . ? C14 C15 1.386(6) . ? C14 H14 0.9500 . ? C15 S16 1.788(4) . ? S16 C17 1.820(5) . ? C17 C18 1.513(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 S19 1.817(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? S19 C20 1.796(4) . ? C20 C21 1.386(6) . ? C20 C25 1.396(6) . ? C21 C22 1.390(6) . ? C21 H21 0.9500 . ? C22 C23 1.395(6) . ? C22 H22 0.9500 . ? C23 C24 1.390(6) . ? C23 H23 0.9500 . ? C24 C25 1.388(6) . ? C24 H24 0.9500 . ? C25 N26 1.429(5) . ? N26 C27 1.299(5) . ? C27 C28 1.435(6) . ? C27 H27 0.9500 . ? C28 C29 1.426(6) . ? C28 C33 1.432(6) . ? C29 C30 1.360(6) . ? C29 H29 0.9500 . ? C30 C31 1.415(7) . ? C30 H30 0.9500 . ? C31 C32 1.361(7) . ? C31 H31 0.9500 . ? C32 C33 1.420(6) . ? C32 H32 0.9500 . ? C33 O34 1.293(5) . ? 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 O34 104.25(13) . . ? O1 Zn1 N9 91.82(12) . . ? O34 Zn1 N9 99.45(13) . . ? O1 Zn1 N26 96.68(12) . . ? O34 Zn1 N26 90.07(12) . . ? N9 Zn1 N26 165.31(13) . . ? O1 Zn1 S16 168.21(10) . . ? O34 Zn1 S16 86.03(9) . . ? N9 Zn1 S16 80.66(10) . . ? N26 Zn1 S16 88.94(10) . . ? O1 Zn1 S19 90.50(9) . . ? O34 Zn1 S19 162.64(9) . . ? N9 Zn1 S19 89.01(10) . . ? N26 Zn1 S19 78.99(10) . . ? S16 Zn1 S19 80.38(4) . . ? C2 O1 Zn1 123.4(3) . . ? O1 C2 C3 119.2(4) . . ? O1 C2 C7 124.5(4) . . ? C3 C2 C7 116.3(4) . . ? C4 C3 C2 122.8(4) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 120.6(4) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.6(4) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 122.3(4) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C6 C7 C2 119.4(4) . . ? C6 C7 C8 115.4(4) . . ? C2 C7 C8 125.2(4) . . ? N9 C8 C7 127.3(4) . . ? N9 C8 H8 116.3 . . ? C7 C8 H8 116.3 . . ? C8 N9 C10 119.1(3) . . ? C8 N9 Zn1 118.4(3) . . ? C10 N9 Zn1 121.9(3) . . ? C11 C10 C15 117.5(4) . . ? C11 C10 N9 123.0(4) . . ? C15 C10 N9 119.4(4) . . ? C12 C11 C10 121.9(4) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C13 C12 C11 120.1(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.9(4) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C14 C15 C10 120.5(4) . . ? C14 C15 S16 118.1(3) . . ? C10 C15 S16 121.4(3) . . ? C15 S16 C17 103.2(2) . . ? C15 S16 Zn1 95.40(14) . . ? C17 S16 Zn1 103.54(15) . . ? C18 C17 S16 115.2(3) . . ? C18 C17 H17A 108.5 . . ? S16 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? S16 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 S19 116.6(3) . . ? C17 C18 H18A 108.2 . . ? S19 C18 H18A 108.2 . . ? C17 C18 H18B 108.2 . . ? S19 C18 H18B 108.2 . . ? H18A C18 H18B 107.3 . . ? C20 S19 C18 104.2(2) . . ? C20 S19 Zn1 92.61(15) . . ? C18 S19 Zn1 104.67(15) . . ? C21 C20 C25 121.0(4) . . ? C21 C20 S19 116.7(3) . . ? C25 C20 S19 121.9(3) . . ? C20 C21 C22 120.1(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 119.1(4) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C24 C23 C22 120.6(4) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 120.4(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C20 118.8(4) . . ? C24 C25 N26 121.5(4) . . ? C20 C25 N26 119.7(4) . . ? C27 N26 C25 118.7(4) . . ? C27 N26 Zn1 122.1(3) . . ? C25 N26 Zn1 119.1(3) . . ? N26 C27 C28 127.6(4) . . ? N26 C27 H27 116.2 . . ? C28 C27 H27 116.2 . . ? C29 C28 C33 118.9(4) . . ? C29 C28 C27 116.4(4) . . ? C33 C28 C27 124.7(4) . . ? C30 C29 C28 122.3(4) . . ? C30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? C29 C30 C31 118.4(4) . . ? C29 C30 H30 120.8 . . ? C31 C30 H30 120.8 . . ? C32 C31 C30 121.2(5) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C33 122.1(5) . . ? C31 C32 H32 118.9 . . ? C33 C32 H32 118.9 . . ? O34 C33 C32 119.4(4) . . ? O34 C33 C28 123.6(4) . . ? C32 C33 C28 116.9(4) . . ? C33 O34 Zn1 126.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O34 Zn1 O1 C2 -68.4(3) . . . . ? N9 Zn1 O1 C2 31.9(3) . . . . ? N26 Zn1 O1 C2 -160.1(3) . . . . ? S16 Zn1 O1 C2 81.8(6) . . . . ? S19 Zn1 O1 C2 120.9(3) . . . . ? Zn1 O1 C2 C3 158.9(3) . . . . ? Zn1 O1 C2 C7 -22.9(6) . . . . ? O1 C2 C3 C4 179.2(4) . . . . ? C7 C2 C3 C4 0.9(6) . . . . ? C2 C3 C4 C5 -0.7(7) . . . . ? C3 C4 C5 C6 0.3(7) . . . . ? C4 C5 C6 C7 0.0(7) . . . . ? C5 C6 C7 C2 0.2(6) . . . . ? C5 C6 C7 C8 -178.4(4) . . . . ? O1 C2 C7 C6 -178.8(4) . . . . ? C3 C2 C7 C6 -0.6(6) . . . . ? O1 C2 C7 C8 -0.4(7) . . . . ? C3 C2 C7 C8 177.8(4) . . . . ? C6 C7 C8 N9 -179.0(4) . . . . ? C2 C7 C8 N9 2.5(7) . . . . ? C7 C8 N9 C10 -172.1(4) . . . . ? C7 C8 N9 Zn1 16.9(5) . . . . ? O1 Zn1 N9 C8 -28.1(3) . . . . ? O34 Zn1 N9 C8 76.7(3) . . . . ? N26 Zn1 N9 C8 -153.6(5) . . . . ? S16 Zn1 N9 C8 161.0(3) . . . . ? S19 Zn1 N9 C8 -118.6(3) . . . . ? O1 Zn1 N9 C10 161.2(3) . . . . ? O34 Zn1 N9 C10 -94.0(3) . . . . ? N26 Zn1 N9 C10 35.8(7) . . . . ? S16 Zn1 N9 C10 -9.7(3) . . . . ? S19 Zn1 N9 C10 70.7(3) . . . . ? C8 N9 C10 C11 19.9(6) . . . . ? Zn1 N9 C10 C11 -169.4(3) . . . . ? C8 N9 C10 C15 -163.5(4) . . . . ? Zn1 N9 C10 C15 7.1(5) . . . . ? C15 C10 C11 C12 2.7(7) . . . . ? N9 C10 C11 C12 179.3(4) . . . . ? C10 C11 C12 C13 -0.6(7) . . . . ? C11 C12 C13 C14 -1.4(7) . . . . ? C12 C13 C14 C15 1.2(7) . . . . ? C13 C14 C15 C10 1.0(7) . . . . ? C13 C14 C15 S16 178.3(4) . . . . ? C11 C10 C15 C14 -2.9(6) . . . . ? N9 C10 C15 C14 -179.6(4) . . . . ? C11 C10 C15 S16 179.9(3) . . . . ? N9 C10 C15 S16 3.2(5) . . . . ? C14 C15 S16 C17 68.7(4) . . . . ? C10 C15 S16 C17 -114.0(4) . . . . ? C14 C15 S16 Zn1 174.0(3) . . . . ? C10 C15 S16 Zn1 -8.7(3) . . . . ? O1 Zn1 S16 C15 -42.4(5) . . . . ? O34 Zn1 S16 C15 108.68(16) . . . . ? N9 Zn1 S16 C15 8.42(17) . . . . ? N26 Zn1 S16 C15 -161.17(16) . . . . ? S19 Zn1 S16 C15 -82.17(14) . . . . ? O1 Zn1 S16 C17 62.6(5) . . . . ? O34 Zn1 S16 C17 -146.29(18) . . . . ? N9 Zn1 S16 C17 113.44(19) . . . . ? N26 Zn1 S16 C17 -56.15(19) . . . . ? S19 Zn1 S16 C17 22.86(16) . . . . ? C15 S16 C17 C18 51.8(4) . . . . ? Zn1 S16 C17 C18 -47.2(4) . . . . ? S16 C17 C18 S19 50.0(5) . . . . ? C17 C18 S19 C20 72.7(4) . . . . ? C17 C18 S19 Zn1 -23.9(4) . . . . ? O1 Zn1 S19 C20 79.13(16) . . . . ? O34 Zn1 S19 C20 -69.4(3) . . . . ? N9 Zn1 S19 C20 170.93(16) . . . . ? N26 Zn1 S19 C20 -17.58(17) . . . . ? S16 Zn1 S19 C20 -108.38(14) . . . . ? O1 Zn1 S19 C18 -175.42(19) . . . . ? O34 Zn1 S19 C18 36.1(4) . . . . ? N9 Zn1 S19 C18 -83.61(19) . . . . ? N26 Zn1 S19 C18 87.87(19) . . . . ? S16 Zn1 S19 C18 -2.92(17) . . . . ? C18 S19 C20 C21 93.1(4) . . . . ? Zn1 S19 C20 C21 -161.1(3) . . . . ? C18 S19 C20 C25 -94.7(4) . . . . ? Zn1 S19 C20 C25 11.2(4) . . . . ? C25 C20 C21 C22 -0.1(7) . . . . ? S19 C20 C21 C22 172.3(3) . . . . ? C20 C21 C22 C23 -1.5(7) . . . . ? C21 C22 C23 C24 2.0(7) . . . . ? C22 C23 C24 C25 -0.9(7) . . . . ? C23 C24 C25 C20 -0.7(6) . . . . ? C23 C24 C25 N26 -178.5(4) . . . . ? C21 C20 C25 C24 1.2(6) . . . . ? S19 C20 C25 C24 -170.7(3) . . . . ? C21 C20 C25 N26 179.0(4) . . . . ? S19 C20 C25 N26 7.1(5) . . . . ? C24 C25 N26 C27 -33.6(6) . . . . ? C20 C25 N26 C27 148.7(4) . . . . ? C24 C25 N26 Zn1 148.9(3) . . . . ? C20 C25 N26 Zn1 -28.9(5) . . . . ? O1 Zn1 N26 C27 120.1(3) . . . . ? O34 Zn1 N26 C27 15.7(3) . . . . ? N9 Zn1 N26 C27 -115.0(5) . . . . ? S16 Zn1 N26 C27 -70.3(3) . . . . ? S19 Zn1 N26 C27 -150.7(3) . . . . ? O1 Zn1 N26 C25 -62.5(3) . . . . ? O34 Zn1 N26 C25 -166.8(3) . . . . ? N9 Zn1 N26 C25 62.4(6) . . . . ? S16 Zn1 N26 C25 107.1(3) . . . . ? S19 Zn1 N26 C25 26.7(3) . . . . ? C25 N26 C27 C28 178.9(4) . . . . ? Zn1 N26 C27 C28 -3.6(6) . . . . ? N26 C27 C28 C29 176.3(4) . . . . ? N26 C27 C28 C33 -7.3(7) . . . . ? C33 C28 C29 C30 3.8(6) . . . . ? C27 C28 C29 C30 -179.7(4) . . . . ? C28 C29 C30 C31 -0.5(7) . . . . ? C29 C30 C31 C32 -1.1(7) . . . . ? C30 C31 C32 C33 -0.7(8) . . . . ? C31 C32 C33 O34 -174.3(4) . . . . ? C31 C32 C33 C28 3.9(7) . . . . ? C29 C28 C33 O34 172.8(4) . . . . ? C27 C28 C33 O34 -3.4(7) . . . . ? C29 C28 C33 C32 -5.3(6) . . . . ? C27 C28 C33 C32 178.5(4) . . . . ? C32 C33 O34 Zn1 -157.7(3) . . . . ? C28 C33 O34 Zn1 24.3(6) . . . . ? O1 Zn1 O34 C33 -123.3(3) . . . . ? N9 Zn1 O34 C33 142.4(3) . . . . ? N26 Zn1 O34 C33 -26.4(4) . . . . ? S16 Zn1 O34 C33 62.6(3) . . . . ? S19 Zn1 O34 C33 24.1(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.217 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.054 data_cpr104 _database_code_CSD 216929 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N2 Ni O2 S2' _chemical_formula_weight 541.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P41 _symmetry_Int_Tables_number 76 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 11.233(1) _cell_length_b 11.233(1) _cell_length_c 18.428(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2325.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10335 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 30 mm; 120 sec./deg., 1 deg., 121 frames; mos. = 0.510(4) deg. ; _diffrn_ambient_temperature 150(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8895 _diffrn_reflns_av_R_equivalents 0.1088 _diffrn_reflns_av_sigmaI/netI 0.1760 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3999 _reflns_number_gt 2718 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L.Spek, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1253P)^2^+136.0262P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.59(10) _refine_ls_number_reflns 3999 _refine_ls_number_parameters 142 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2345 _refine_ls_R_factor_gt 0.1940 _refine_ls_wR_factor_ref 0.4559 _refine_ls_wR_factor_gt 0.4342 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _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 Ni1 Ni 0.7724(3) 0.2836(3) 0.20143(19) 0.0282(9) Uiso 1 1 d . . . O1 O 0.909(2) 0.344(2) 0.2509(13) 0.057(6) Uiso 1 1 d . . . C2 C 1.009(2) 0.274(2) 0.2656(14) 0.030(6) Uiso 1 1 d . . . C3 C 1.093(3) 0.309(3) 0.3226(17) 0.043(7) Uiso 1 1 d . . . H3 H 1.0755 0.3761 0.3523 0.051 Uiso 1 1 calc R . . C4 C 1.191(4) 0.249(4) 0.332(2) 0.072(12) Uiso 1 1 d . . . H4 H 1.2455 0.2760 0.3681 0.087 Uiso 1 1 calc R . . C5 C 1.220(2) 0.147(2) 0.2938(13) 0.022(5) Uiso 1 1 d . . . H5 H 1.2874 0.0998 0.3054 0.026 Uiso 1 1 calc R . . C6 C 1.149(3) 0.119(3) 0.2415(18) 0.052(9) Uiso 1 1 d . . . H6 H 1.1724 0.0548 0.2110 0.063 Uiso 1 1 calc R . . C7 C 1.046(2) 0.172(2) 0.2264(13) 0.023(5) Uiso 1 1 d . . . C8 C 0.967(3) 0.139(3) 0.1641(18) 0.049(8) Uiso 1 1 d . . . H8 H 1.0021 0.0830 0.1318 0.059 Uiso 1 1 calc R . . N9 N 0.8609(18) 0.1704(18) 0.1454(11) 0.025(5) Uiso 1 1 d . . . C10 C 0.808(2) 0.115(2) 0.0873(12) 0.020(5) Uiso 1 1 d . . . C11 C 0.874(3) 0.052(3) 0.0272(15) 0.037(7) Uiso 1 1 d . . . H11 H 0.9584 0.0501 0.0282 0.044 Uiso 1 1 calc R . . C12 C 0.817(2) 0.002(2) -0.0260(13) 0.027(6) Uiso 1 1 d . . . H12 H 0.8620 -0.0373 -0.0626 0.032 Uiso 1 1 calc R . . C13 C 0.687(3) 0.002(3) -0.0320(18) 0.045(8) Uiso 1 1 d . . . H13 H 0.6481 -0.0313 -0.0728 0.054 Uiso 1 1 calc R . . C14 C 0.625(2) 0.053(2) 0.0239(14) 0.028(6) Uiso 1 1 d . . . H14 H 0.5403 0.0548 0.0224 0.033 Uiso 1 1 calc R . . C15 C 0.682(2) 0.101(2) 0.0808(12) 0.017(5) Uiso 1 1 d . . . S16 S 0.5951(7) 0.1909(7) 0.1454(4) 0.0367(18) Uiso 1 1 d . . . C17 C 0.555(2) 0.088(2) 0.2095(16) 0.037(7) Uiso 1 1 d . . . H17A H 0.4900 0.1214 0.2397 0.045 Uiso 1 1 calc R . . H17B H 0.5236 0.0163 0.1848 0.045 Uiso 1 1 calc R . . C18 C 0.664(2) 0.050(2) 0.2617(14) 0.025(5) Uiso 1 1 d . . . H18A H 0.7207 0.0020 0.2324 0.030 Uiso 1 1 calc R . . H18B H 0.6320 -0.0037 0.2998 0.030 Uiso 1 1 calc R . . S19 S 0.7408(7) 0.1566(7) 0.3026(4) 0.0362(18) Uiso 1 1 d . . . C20 C 0.630(2) 0.243(2) 0.3523(14) 0.028(6) Uiso 1 1 d . . . C21 C 0.558(3) 0.203(3) 0.4062(18) 0.053(9) Uiso 1 1 d . . . H21 H 0.5643 0.1213 0.4182 0.063 Uiso 1 1 calc R . . C22 C 0.484(3) 0.265(3) 0.4425(18) 0.045(7) Uiso 1 1 d . . . H22 H 0.4450 0.2330 0.4840 0.053 Uiso 1 1 calc R . . C23 C 0.461(3) 0.381(3) 0.4190(17) 0.043(7) Uiso 1 1 d . . . H23 H 0.4090 0.4312 0.4460 0.052 Uiso 1 1 calc R . . C24 C 0.512(3) 0.421(3) 0.3594(16) 0.036(7) Uiso 1 1 d . . . H24 H 0.4842 0.4936 0.3384 0.044 Uiso 1 1 calc R . . C25 C 0.608(3) 0.357(3) 0.3257(16) 0.037(7) Uiso 1 1 d . . . N26 N 0.6505(18) 0.4030(18) 0.2566(10) 0.022(4) Uiso 1 1 d . . . C27 C 0.662(2) 0.518(2) 0.2399(15) 0.033(6) Uiso 1 1 d . . . H27 H 0.6314 0.5706 0.2753 0.040 Uiso 1 1 calc R . . C28 C 0.711(2) 0.573(2) 0.1814(14) 0.030(6) Uiso 1 1 d . . . C29 C 0.703(3) 0.704(3) 0.1737(17) 0.043(7) Uiso 1 1 d . . . H29 H 0.6754 0.7489 0.2138 0.052 Uiso 1 1 calc R . . C30 C 0.731(2) 0.757(3) 0.1170(14) 0.032(6) Uiso 1 1 d . . . H30 H 0.7244 0.8417 0.1154 0.038 Uiso 1 1 calc R . . C31 C 0.7700(17) 0.7010(17) 0.0599(11) 0.006(4) Uiso 1 1 d . . . H31 H 0.7823 0.7421 0.0155 0.008 Uiso 1 1 calc R . . C32 C 0.793(3) 0.581(3) 0.0648(17) 0.042(7) Uiso 1 1 d . . . H32 H 0.8333 0.5447 0.0254 0.051 Uiso 1 1 calc R . . C33 C 0.762(3) 0.511(3) 0.1213(15) 0.035(7) Uiso 1 1 d . . . O34 O 0.7736(18) 0.3929(18) 0.1152(11) 0.042(5) Uiso 1 1 d . . . _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 Ni1 O1 1.91(2) . ? Ni1 N9 1.92(2) . ? Ni1 O34 2.01(2) . ? Ni1 N26 2.17(2) . ? Ni1 S19 2.373(8) . ? Ni1 S16 2.473(8) . ? O1 C2 1.39(3) . ? C2 C7 1.41(4) . ? C2 C3 1.46(4) . ? C3 C4 1.31(5) . ? C3 H3 0.9500 . ? C4 C5 1.39(5) . ? C4 H4 0.9500 . ? C5 C6 1.29(4) . ? C5 H5 0.9500 . ? C6 C7 1.33(4) . ? C6 H6 0.9500 . ? C7 C8 1.50(4) . ? C8 N9 1.29(4) . ? C8 H8 0.9500 . ? N9 C10 1.38(3) . ? C10 C15 1.42(3) . ? C10 C11 1.51(4) . ? C11 C12 1.30(4) . ? C11 H11 0.9500 . ? C12 C13 1.46(4) . ? C12 H12 0.9500 . ? C13 C14 1.37(4) . ? C13 H13 0.9500 . ? C14 C15 1.35(3) . ? C14 H14 0.9500 . ? C15 S16 1.84(2) . ? S16 C17 1.71(3) . ? C17 C18 1.62(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 S19 1.66(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? S19 C20 1.83(3) . ? C20 C21 1.35(4) . ? C20 C25 1.40(4) . ? C21 C22 1.28(4) . ? C21 H21 0.9500 . ? C22 C23 1.40(4) . ? C22 H22 0.9500 . ? C23 C24 1.32(4) . ? C23 H23 0.9500 . ? C24 C25 1.44(4) . ? C24 H24 0.9500 . ? C25 N26 1.45(3) . ? N26 C27 1.33(3) . ? C27 C28 1.36(4) . ? C27 H27 0.9500 . ? C28 C33 1.42(4) . ? C28 C29 1.48(4) . ? C29 C30 1.25(4) . ? C29 H29 0.9500 . ? C30 C31 1.30(3) . ? C30 H30 0.9500 . ? C31 C32 1.37(4) . ? C31 H31 0.9500 . ? C32 C33 1.35(4) . ? C32 H32 0.9500 . ? C33 O34 1.34(3) . ? 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 Ni1 N9 94.2(9) . . ? O1 Ni1 O34 98.9(9) . . ? N9 Ni1 O34 88.6(8) . . ? O1 Ni1 N26 93.8(9) . . ? N9 Ni1 N26 172.0(9) . . ? O34 Ni1 N26 89.8(8) . . ? O1 Ni1 S19 87.6(7) . . ? N9 Ni1 S19 95.9(6) . . ? O34 Ni1 S19 171.8(7) . . ? N26 Ni1 S19 84.8(6) . . ? O1 Ni1 S16 174.9(7) . . ? N9 Ni1 S16 85.0(6) . . ? O34 Ni1 S16 86.1(6) . . ? N26 Ni1 S16 87.0(6) . . ? S19 Ni1 S16 87.4(3) . . ? C2 O1 Ni1 122.6(19) . . ? O1 C2 C7 126(2) . . ? O1 C2 C3 120(2) . . ? C7 C2 C3 113(2) . . ? C4 C3 C2 120(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 124(4) . . ? C3 C4 H4 118.2 . . ? C5 C4 H4 118.2 . . ? C6 C5 C4 116(3) . . ? C6 C5 H5 121.9 . . ? C4 C5 H5 121.9 . . ? C5 C6 C7 126(3) . . ? C5 C6 H6 117.2 . . ? C7 C6 H6 117.2 . . ? C6 C7 C2 121(3) . . ? C6 C7 C8 124(3) . . ? C2 C7 C8 115(2) . . ? N9 C8 C7 133(3) . . ? N9 C8 H8 113.5 . . ? C7 C8 H8 113.5 . . ? C8 N9 C10 119(2) . . ? C8 N9 Ni1 121(2) . . ? C10 N9 Ni1 119.7(16) . . ? N9 C10 C15 123(2) . . ? N9 C10 C11 125(2) . . ? C15 C10 C11 112(2) . . ? C12 C11 C10 121(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 123(3) . . ? C11 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C14 C13 C12 117(3) . . ? C14 C13 H13 121.5 . . ? C12 C13 H13 121.5 . . ? C15 C14 C13 120(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 126(2) . . ? C14 C15 S16 117.8(18) . . ? C10 C15 S16 114.6(17) . . ? C17 S16 C15 102.6(12) . . ? C17 S16 Ni1 102.0(10) . . ? C15 S16 Ni1 94.0(8) . . ? C18 C17 S16 113.0(18) . . ? C18 C17 H17A 109.0 . . ? S16 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? S16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 S19 118.0(18) . . ? C17 C18 H18A 107.8 . . ? S19 C18 H18A 107.8 . . ? C17 C18 H18B 107.8 . . ? S19 C18 H18B 107.8 . . ? H18A C18 H18B 107.1 . . ? C18 S19 C20 105.1(13) . . ? C18 S19 Ni1 99.0(9) . . ? C20 S19 Ni1 100.1(9) . . ? C21 C20 C25 117(3) . . ? C21 C20 S19 127(2) . . ? C25 C20 S19 116(2) . . ? C22 C21 C20 127(3) . . ? C22 C21 H21 116.7 . . ? C20 C21 H21 116.7 . . ? C21 C22 C23 118(3) . . ? C21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? C24 C23 C22 120(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 121(3) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C20 C25 C24 116(3) . . ? C20 C25 N26 125(2) . . ? C24 C25 N26 117(2) . . ? C27 N26 C25 125(2) . . ? C27 N26 Ni1 115.2(17) . . ? C25 N26 Ni1 113.6(16) . . ? N26 C27 C28 132(3) . . ? N26 C27 H27 114.1 . . ? C28 C27 H27 114.1 . . ? C27 C28 C33 124(3) . . ? C27 C28 C29 120(3) . . ? C33 C28 C29 115(2) . . ? C30 C29 C28 123(3) . . ? C30 C29 H29 118.4 . . ? C28 C29 H29 118.4 . . ? C29 C30 C31 122(3) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C30 C31 C32 119(2) . . ? C30 C31 H31 120.5 . . ? C32 C31 H31 120.5 . . ? C33 C32 C31 125(3) . . ? C33 C32 H32 117.6 . . ? C31 C32 H32 117.6 . . ? O34 C33 C32 119(3) . . ? O34 C33 C28 126(3) . . ? C32 C33 C28 115(3) . . ? C33 O34 Ni1 122.7(18) . . ? 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 N9 Ni1 O1 C2 -30(2) . . . . ? O34 Ni1 O1 C2 -120(2) . . . . ? N26 Ni1 O1 C2 150(2) . . . . ? S19 Ni1 O1 C2 65(2) . . . . ? S16 Ni1 O1 C2 51(10) . . . . ? Ni1 O1 C2 C7 26(4) . . . . ? Ni1 O1 C2 C3 -160(2) . . . . ? O1 C2 C3 C4 -175(3) . . . . ? C7 C2 C3 C4 1(4) . . . . ? C2 C3 C4 C5 -3(6) . . . . ? C3 C4 C5 C6 6(6) . . . . ? C4 C5 C6 C7 -7(5) . . . . ? C5 C6 C7 C2 5(5) . . . . ? C5 C6 C7 C8 179(3) . . . . ? O1 C2 C7 C6 174(3) . . . . ? C3 C2 C7 C6 -1(4) . . . . ? O1 C2 C7 C8 -1(4) . . . . ? C3 C2 C7 C8 -176(2) . . . . ? C6 C7 C8 N9 172(3) . . . . ? C2 C7 C8 N9 -14(5) . . . . ? C7 C8 N9 C10 -174(3) . . . . ? C7 C8 N9 Ni1 1(5) . . . . ? O1 Ni1 N9 C8 18(2) . . . . ? O34 Ni1 N9 C8 117(2) . . . . ? N26 Ni1 N9 C8 -164(5) . . . . ? S19 Ni1 N9 C8 -70(2) . . . . ? S16 Ni1 N9 C8 -157(2) . . . . ? O1 Ni1 N9 C10 -167.0(18) . . . . ? O34 Ni1 N9 C10 -68.2(18) . . . . ? N26 Ni1 N9 C10 11(7) . . . . ? S19 Ni1 N9 C10 104.9(17) . . . . ? S16 Ni1 N9 C10 18.1(17) . . . . ? C8 N9 C10 C15 152(3) . . . . ? Ni1 N9 C10 C15 -24(3) . . . . ? C8 N9 C10 C11 -23(4) . . . . ? Ni1 N9 C10 C11 161.8(19) . . . . ? N9 C10 C11 C12 180(2) . . . . ? C15 C10 C11 C12 5(4) . . . . ? C10 C11 C12 C13 1(4) . . . . ? C11 C12 C13 C14 -4(4) . . . . ? C12 C13 C14 C15 1(4) . . . . ? C13 C14 C15 C10 6(4) . . . . ? C13 C14 C15 S16 170(2) . . . . ? N9 C10 C15 C14 177(2) . . . . ? C11 C10 C15 C14 -8(4) . . . . ? N9 C10 C15 S16 12(3) . . . . ? C11 C10 C15 S16 -172.5(17) . . . . ? C14 C15 S16 C17 93(2) . . . . ? C10 C15 S16 C17 -102(2) . . . . ? C14 C15 S16 Ni1 -164.2(19) . . . . ? C10 C15 S16 Ni1 1.4(18) . . . . ? O1 Ni1 S16 C17 13(9) . . . . ? N9 Ni1 S16 C17 94.6(12) . . . . ? O34 Ni1 S16 C17 -176.4(12) . . . . ? N26 Ni1 S16 C17 -86.4(11) . . . . ? S19 Ni1 S16 C17 -1.5(10) . . . . ? O1 Ni1 S16 C15 -91(9) . . . . ? N9 Ni1 S16 C15 -9.2(10) . . . . ? O34 Ni1 S16 C15 79.8(9) . . . . ? N26 Ni1 S16 C15 169.8(9) . . . . ? S19 Ni1 S16 C15 -105.3(8) . . . . ? C15 S16 C17 C18 74(2) . . . . ? Ni1 S16 C17 C18 -23(2) . . . . ? S16 C17 C18 S19 52(3) . . . . ? C17 C18 S19 C20 56(2) . . . . ? C17 C18 S19 Ni1 -48(2) . . . . ? O1 Ni1 S19 C18 -155.3(11) . . . . ? N9 Ni1 S19 C18 -61.3(12) . . . . ? O34 Ni1 S19 C18 62(5) . . . . ? N26 Ni1 S19 C18 110.7(11) . . . . ? S16 Ni1 S19 C18 23.5(9) . . . . ? O1 Ni1 S19 C20 97.5(11) . . . . ? N9 Ni1 S19 C20 -168.5(11) . . . . ? O34 Ni1 S19 C20 -46(5) . . . . ? N26 Ni1 S19 C20 3.4(10) . . . . ? S16 Ni1 S19 C20 -83.8(9) . . . . ? C18 S19 C20 C21 61(3) . . . . ? Ni1 S19 C20 C21 164(3) . . . . ? C18 S19 C20 C25 -110(2) . . . . ? Ni1 S19 C20 C25 -8(2) . . . . ? C25 C20 C21 C22 -11(5) . . . . ? S19 C20 C21 C22 178(3) . . . . ? C20 C21 C22 C23 9(5) . . . . ? C21 C22 C23 C24 3(5) . . . . ? C22 C23 C24 C25 -13(5) . . . . ? C21 C20 C25 C24 1(4) . . . . ? S19 C20 C25 C24 173(2) . . . . ? C21 C20 C25 N26 -162(3) . . . . ? S19 C20 C25 N26 11(4) . . . . ? C23 C24 C25 C20 10(4) . . . . ? C23 C24 C25 N26 174(3) . . . . ? C20 C25 N26 C27 -158(3) . . . . ? C24 C25 N26 C27 39(4) . . . . ? C20 C25 N26 Ni1 -7(3) . . . . ? C24 C25 N26 Ni1 -170(2) . . . . ? O1 Ni1 N26 C27 67.8(19) . . . . ? N9 Ni1 N26 C27 -110(6) . . . . ? O34 Ni1 N26 C27 -31.1(19) . . . . ? S19 Ni1 N26 C27 155.1(18) . . . . ? S16 Ni1 N26 C27 -117.3(18) . . . . ? O1 Ni1 N26 C25 -86.6(18) . . . . ? N9 Ni1 N26 C25 96(6) . . . . ? O34 Ni1 N26 C25 174.5(18) . . . . ? S19 Ni1 N26 C25 0.7(17) . . . . ? S16 Ni1 N26 C25 88.3(17) . . . . ? C25 N26 C27 C28 173(3) . . . . ? Ni1 N26 C27 C28 22(4) . . . . ? N26 C27 C28 C33 1(5) . . . . ? N26 C27 C28 C29 175(3) . . . . ? C27 C28 C29 C30 -170(3) . . . . ? C33 C28 C29 C30 4(4) . . . . ? C28 C29 C30 C31 0(5) . . . . ? C29 C30 C31 C32 -7(4) . . . . ? C30 C31 C32 C33 11(4) . . . . ? C31 C32 C33 O34 171(3) . . . . ? C31 C32 C33 C28 -6(4) . . . . ? C27 C28 C33 O34 -3(5) . . . . ? C29 C28 C33 O34 -178(3) . . . . ? C27 C28 C33 C32 173(3) . . . . ? C29 C28 C33 C32 -2(4) . . . . ? C32 C33 O34 Ni1 163(2) . . . . ? C28 C33 O34 Ni1 -21(4) . . . . ? O1 Ni1 O34 C33 -62(2) . . . . ? N9 Ni1 O34 C33 -156(2) . . . . ? N26 Ni1 O34 C33 32(2) . . . . ? S19 Ni1 O34 C33 81(5) . . . . ? S16 Ni1 O34 C33 119(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.055 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.276 data_rao004 _database_code_CSD 216930 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36.50 H28 N2 Ni O2.50 S2' _chemical_formula_weight 657.44 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' Ni Ni 0.3393 1.1124 '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_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.750(1) _cell_length_b 12.299(1) _cell_length_c 12.656(1) _cell_angle_alpha 84.38(1) _cell_angle_beta 67.41(1) _cell_angle_gamma 70.99(1) _cell_volume 1460.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1664 _cell_measurement_theta_min 7 _cell_measurement_theta_max 25 _exptl_crystal_description Blocks _exptl_crystal_colour Red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 682 _exptl_absorpt_coefficient_mu 0.848 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 30 mm; 40 sec./deg.; 1 deg ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotations in Phi and Omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5901 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.69 _reflns_number_total 4324 _reflns_number_gt 3368 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L.Spek, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0310P)^2^+2.9621P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4324 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Ni1 Ni 0.74256(6) 0.74462(5) 0.51001(4) 0.01982(17) Uani 1 1 d . . . O1 O 0.5392(3) 0.7493(3) 0.5942(2) 0.0256(7) Uani 1 1 d . . . C2 C 0.4565(4) 0.8074(4) 0.6887(3) 0.0229(9) Uani 1 1 d . . . C3 C 0.3335(5) 0.7752(4) 0.7576(4) 0.0279(10) Uani 1 1 d . . . H3 H 0.3175 0.7144 0.7322 0.034 Uiso 1 1 calc R . . C4 C 0.2393(5) 0.8304(4) 0.8586(4) 0.0308(11) Uani 1 1 d . . . H4 H 0.1590 0.8085 0.8994 0.037 Uiso 1 1 calc R . . C5 C 0.2624(5) 0.9222(4) 0.9031(4) 0.0270(10) Uani 1 1 d . . . C6 C 0.1685(5) 0.9750(4) 1.0108(4) 0.0333(11) Uani 1 1 d . . . H6 H 0.0886 0.9527 1.0516 0.040 Uiso 1 1 calc R . . C7 C 0.1936(5) 1.0584(5) 1.0560(4) 0.0397(13) Uani 1 1 d . . . H7 H 0.1301 1.0942 1.1263 0.048 Uiso 1 1 calc R . . C8 C 0.3154(6) 1.0894(4) 0.9956(4) 0.0384(12) Uani 1 1 d . . . H8 H 0.3333 1.1451 1.0271 0.046 Uiso 1 1 calc R . . C9 C 0.4102(5) 1.0395(4) 0.8900(4) 0.0322(11) Uani 1 1 d . . . H9 H 0.4911 1.0613 0.8518 0.039 Uiso 1 1 calc R . . C10 C 0.3844(5) 0.9550(4) 0.8399(3) 0.0238(9) Uani 1 1 d . . . C11 C 0.4788(4) 0.9020(4) 0.7267(3) 0.0212(9) Uani 1 1 d . . . C12 C 0.5834(4) 0.9527(4) 0.6545(3) 0.0217(9) Uani 1 1 d . . . H12 H 0.5798 1.0220 0.6809 0.026 Uiso 1 1 calc R . . N13 N 0.6832(4) 0.9127(3) 0.5560(3) 0.0213(8) Uani 1 1 d . . . C14 C 0.7711(4) 0.9804(4) 0.4944(3) 0.0199(9) Uani 1 1 d . . . C15 C 0.7247(5) 1.1003(4) 0.5006(3) 0.0227(9) Uani 1 1 d . . . H15 H 0.6309 1.1398 0.5446 0.027 Uiso 1 1 calc R . . C16 C 0.8179(5) 1.1609(4) 0.4415(4) 0.0289(10) Uani 1 1 d . . . H16 H 0.7858 1.2409 0.4471 0.035 Uiso 1 1 calc R . . C17 C 0.9587(5) 1.1048(4) 0.3737(4) 0.0265(10) Uani 1 1 d . . . H17 H 1.0213 1.1461 0.3363 0.032 Uiso 1 1 calc R . . C18 C 1.0033(4) 0.9852(4) 0.3636(3) 0.0231(9) Uani 1 1 d . . . H18 H 1.0964 0.9461 0.3177 0.028 Uiso 1 1 calc R . . C19 C 0.9105(4) 0.9239(4) 0.4214(3) 0.0228(9) Uani 1 1 d . . . S20 S 0.97084(11) 0.77130(9) 0.40537(8) 0.0226(2) Uani 1 1 d . . . C21 C 0.9905(5) 0.7589(4) 0.2569(3) 0.0265(10) Uani 1 1 d . . . H21A H 1.0632 0.7917 0.2080 0.032 Uiso 1 1 calc R . . H21B H 1.0220 0.6781 0.2351 0.032 Uiso 1 1 calc R . . C22 C 0.8540(5) 0.8191(4) 0.2374(3) 0.0265(10) Uani 1 1 d . . . H22A H 0.8706 0.8078 0.1577 0.032 Uiso 1 1 calc R . . H22B H 0.8277 0.9010 0.2521 0.032 Uiso 1 1 calc R . . S23 S 0.70695(11) 0.76798(9) 0.32743(9) 0.0240(3) Uani 1 1 d . . . C24 C 0.7835(4) 0.6196(4) 0.2848(3) 0.0233(9) Uani 1 1 d . . . C25 C 0.8020(5) 0.5856(4) 0.1766(4) 0.0310(11) Uani 1 1 d . . . H25 H 0.7695 0.6398 0.1288 0.037 Uiso 1 1 calc R . . C26 C 0.8683(5) 0.4719(4) 0.1401(4) 0.0327(11) Uani 1 1 d . . . H26 H 0.8783 0.4492 0.0685 0.039 Uiso 1 1 calc R . . C27 C 0.9195(5) 0.3919(4) 0.2098(4) 0.0281(10) Uani 1 1 d . . . H27 H 0.9672 0.3158 0.1839 0.034 Uiso 1 1 calc R . . C28 C 0.9005(5) 0.4243(4) 0.3190(4) 0.0254(10) Uani 1 1 d . . . H28 H 0.9353 0.3697 0.3654 0.030 Uiso 1 1 calc R . . C29 C 0.8297(4) 0.5380(4) 0.3587(3) 0.0214(9) Uani 1 1 d . . . N30 N 0.7985(4) 0.5749(3) 0.4716(3) 0.0205(8) Uani 1 1 d . . . C31 C 0.7768(4) 0.5022(4) 0.5537(3) 0.0240(9) Uani 1 1 d . . . H31 H 0.7842 0.4294 0.5322 0.029 Uiso 1 1 calc R . . C32 C 0.7432(4) 0.5205(4) 0.6719(3) 0.0214(9) Uani 1 1 d . . . C33 C 0.6947(5) 0.4378(4) 0.7521(3) 0.0248(10) Uani 1 1 d . . . C34 C 0.6558(5) 0.3477(4) 0.7240(4) 0.0317(11) Uani 1 1 d . . . H34 H 0.6593 0.3422 0.6501 0.038 Uiso 1 1 calc R . . C35 C 0.6133(6) 0.2685(5) 0.8018(4) 0.0393(12) Uani 1 1 d . . . H35 H 0.5899 0.2105 0.7795 0.047 Uiso 1 1 calc R . . C36 C 0.6048(5) 0.2740(5) 0.9140(4) 0.0382(12) Uani 1 1 d . . . H36 H 0.5785 0.2190 0.9661 0.046 Uiso 1 1 calc R . . C37 C 0.6363(5) 0.3627(4) 0.9459(4) 0.0343(12) Uani 1 1 d . . . H37 H 0.6288 0.3682 1.0210 0.041 Uiso 1 1 calc R . . C38 C 0.6792(5) 0.4444(4) 0.8687(4) 0.0301(11) Uani 1 1 d . . . C39 C 0.7086(5) 0.5384(4) 0.9024(4) 0.0298(11) Uani 1 1 d . . . H39 H 0.7019 0.5431 0.9773 0.036 Uiso 1 1 calc R . . C40 C 0.7454(5) 0.6200(4) 0.8297(4) 0.0276(10) Uani 1 1 d . . . H40 H 0.7610 0.6802 0.8566 0.033 Uiso 1 1 calc R . . C41 C 0.7616(4) 0.6173(4) 0.7110(3) 0.0238(10) Uani 1 1 d . . . O42 O 0.7937(3) 0.7001(3) 0.6485(2) 0.0263(7) Uani 1 1 d . . . C1S C 0.5000 0.5000 0.5000 0.072(3) Uani 1 2 d S . . H1S1 H 0.4039 0.5277 0.5537 0.108 Uiso 0.50 1 calc PR . . H1S2 H 0.5032 0.5209 0.4241 0.108 Uiso 0.50 1 calc PR . . H1S3 H 0.5581 0.5336 0.5191 0.108 Uiso 0.50 1 calc PR . . O1S O 0.5473(8) 0.3883(6) 0.5043(7) 0.048(2) Uani 0.50 1 d PD . . H1S H 0.524(13) 0.337(8) 0.485(12) 0.071 Uiso 0.50 1 d PD . . 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 Ni1 0.0218(3) 0.0174(3) 0.0176(3) 0.0045(2) -0.0040(2) -0.0080(2) O1 0.0239(16) 0.0285(17) 0.0236(15) 0.0005(13) -0.0064(12) -0.0100(14) C2 0.023(2) 0.028(2) 0.0167(19) 0.0091(17) -0.0061(17) -0.011(2) C3 0.029(2) 0.032(3) 0.025(2) 0.0057(19) -0.0063(18) -0.017(2) C4 0.026(2) 0.040(3) 0.025(2) 0.012(2) -0.0056(18) -0.017(2) C5 0.024(2) 0.029(2) 0.021(2) 0.0117(18) -0.0050(18) -0.008(2) C6 0.028(3) 0.036(3) 0.022(2) 0.014(2) 0.0011(18) -0.008(2) C7 0.037(3) 0.041(3) 0.019(2) -0.001(2) 0.0057(19) -0.001(3) C8 0.050(3) 0.034(3) 0.023(2) 0.000(2) -0.003(2) -0.015(3) C9 0.035(3) 0.031(3) 0.026(2) -0.001(2) -0.0026(19) -0.015(2) C10 0.026(2) 0.021(2) 0.018(2) 0.0080(17) -0.0057(17) -0.004(2) C11 0.017(2) 0.024(2) 0.0177(19) 0.0037(17) -0.0016(16) -0.0067(19) C12 0.024(2) 0.017(2) 0.021(2) 0.0040(17) -0.0047(17) -0.0078(19) N13 0.0218(18) 0.0195(19) 0.0222(17) 0.0065(14) -0.0059(14) -0.0106(16) C14 0.022(2) 0.021(2) 0.0169(19) 0.0041(16) -0.0051(16) -0.0104(19) C15 0.026(2) 0.020(2) 0.020(2) 0.0061(17) -0.0059(17) -0.010(2) C16 0.039(3) 0.023(2) 0.022(2) 0.0045(18) -0.0078(19) -0.012(2) C17 0.033(3) 0.026(2) 0.025(2) 0.0082(18) -0.0078(19) -0.020(2) C18 0.024(2) 0.027(2) 0.0161(19) 0.0046(17) -0.0023(16) -0.012(2) C19 0.024(2) 0.025(2) 0.022(2) 0.0067(18) -0.0084(17) -0.013(2) S20 0.0207(5) 0.0202(5) 0.0214(5) 0.0050(4) -0.0030(4) -0.0067(5) C21 0.029(2) 0.024(2) 0.019(2) 0.0036(17) 0.0002(17) -0.011(2) C22 0.034(3) 0.027(2) 0.017(2) 0.0087(17) -0.0073(18) -0.012(2) S23 0.0259(6) 0.0226(6) 0.0207(5) 0.0067(4) -0.0077(4) -0.0069(5) C24 0.025(2) 0.027(2) 0.019(2) 0.0031(18) -0.0075(17) -0.012(2) C25 0.036(3) 0.035(3) 0.023(2) 0.005(2) -0.014(2) -0.011(2) C26 0.040(3) 0.039(3) 0.022(2) -0.001(2) -0.010(2) -0.016(2) C27 0.030(2) 0.031(3) 0.023(2) -0.0015(19) -0.0046(18) -0.015(2) C28 0.028(2) 0.025(2) 0.024(2) 0.0049(18) -0.0081(18) -0.012(2) C29 0.021(2) 0.026(2) 0.0167(19) 0.0022(17) -0.0057(16) -0.009(2) N30 0.0265(19) 0.0204(18) 0.0146(16) 0.0060(14) -0.0058(14) -0.0113(16) C31 0.022(2) 0.026(2) 0.022(2) -0.0002(18) -0.0053(17) -0.008(2) C32 0.026(2) 0.020(2) 0.0176(19) 0.0069(17) -0.0079(17) -0.009(2) C33 0.027(2) 0.021(2) 0.022(2) 0.0074(18) -0.0060(18) -0.007(2) C34 0.043(3) 0.026(2) 0.025(2) 0.0085(19) -0.007(2) -0.017(2) C35 0.045(3) 0.029(3) 0.038(3) 0.013(2) -0.006(2) -0.020(3) C36 0.031(3) 0.033(3) 0.031(3) 0.020(2) 0.002(2) -0.009(2) C37 0.026(3) 0.041(3) 0.020(2) 0.010(2) -0.0001(18) -0.004(2) C38 0.020(2) 0.038(3) 0.023(2) 0.006(2) -0.0048(17) -0.002(2) C39 0.025(2) 0.042(3) 0.017(2) 0.003(2) -0.0066(17) -0.006(2) C40 0.030(2) 0.029(2) 0.022(2) -0.0002(19) -0.0101(19) -0.006(2) C41 0.021(2) 0.027(2) 0.021(2) 0.0019(19) -0.0062(17) -0.007(2) O42 0.0316(17) 0.0253(17) 0.0256(15) 0.0049(13) -0.0111(13) -0.0143(15) C1S 0.051(6) 0.069(7) 0.115(9) 0.007(7) -0.040(6) -0.033(6) O1S 0.051(5) 0.030(4) 0.071(5) -0.012(4) -0.037(4) -0.005(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 Ni1 O42 2.008(3) . ? Ni1 O1 2.014(3) . ? Ni1 N30 2.028(3) . ? Ni1 N13 2.028(3) . ? Ni1 S20 2.4138(12) . ? Ni1 S23 2.4591(11) . ? O1 C2 1.292(5) . ? C2 C11 1.422(6) . ? C2 C3 1.432(6) . ? C3 C4 1.359(6) . ? C3 H3 0.9300 . ? C4 C5 1.438(7) . ? C4 H4 0.9300 . ? C5 C6 1.410(6) . ? C5 C10 1.414(7) . ? C6 C7 1.367(7) . ? C6 H6 0.9300 . ? C7 C8 1.394(8) . ? C7 H7 0.9300 . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.418(6) . ? C9 H9 0.9300 . ? C10 C11 1.464(5) . ? C11 C12 1.430(6) . ? C12 N13 1.302(5) . ? C12 H12 0.9300 . ? N13 C14 1.419(6) . ? C14 C15 1.394(6) . ? C14 C19 1.402(6) . ? C15 C16 1.386(7) . ? C15 H15 0.9300 . ? C16 C17 1.393(6) . ? C16 H16 0.9300 . ? C17 C18 1.393(6) . ? C17 H17 0.9300 . ? C18 C19 1.386(6) . ? C18 H18 0.9300 . ? C19 S20 1.779(4) . ? S20 C21 1.825(4) . ? C21 C22 1.516(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 S23 1.821(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? S23 C24 1.781(4) . ? C24 C25 1.392(5) . ? C24 C29 1.407(6) . ? C25 C26 1.379(7) . ? C25 H25 0.9300 . ? C26 C27 1.379(7) . ? C26 H26 0.9300 . ? C27 C28 1.395(5) . ? C27 H27 0.9300 . ? C28 C29 1.392(6) . ? C28 H28 0.9300 . ? C29 N30 1.420(5) . ? N30 C31 1.305(6) . ? C31 C32 1.420(5) . ? C31 H31 0.9300 . ? C32 C41 1.431(6) . ? C32 C33 1.440(6) . ? C33 C34 1.422(7) . ? C33 C38 1.428(6) . ? C34 C35 1.372(7) . ? C34 H34 0.9300 . ? C35 C36 1.394(7) . ? C35 H35 0.9300 . ? C36 C37 1.379(8) . ? C36 H36 0.9300 . ? C37 C38 1.392(7) . ? C37 H37 0.9300 . ? C38 C39 1.433(7) . ? C39 C40 1.345(7) . ? C39 H39 0.9300 . ? C40 C41 1.446(6) . ? C40 H40 0.9300 . ? C41 O42 1.282(6) . ? C1S O1S 1.304(8) . ? C1S H1S1 0.9600 . ? C1S H1S2 0.9600 . ? C1S H1S3 0.9600 . ? O1S H1S 0.840(10) . ? 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 O42 Ni1 O1 93.67(12) . . ? O42 Ni1 N30 88.45(13) . . ? O1 Ni1 N30 90.28(13) . . ? O42 Ni1 N13 89.49(13) . . ? O1 Ni1 N13 88.33(13) . . ? N30 Ni1 N13 177.44(14) . . ? O42 Ni1 S20 90.38(10) . . ? O1 Ni1 S20 170.90(9) . . ? N30 Ni1 S20 97.98(11) . . ? N13 Ni1 S20 83.55(11) . . ? O42 Ni1 S23 170.62(9) . . ? O1 Ni1 S23 90.23(8) . . ? N30 Ni1 S23 82.99(9) . . ? N13 Ni1 S23 99.17(10) . . ? S20 Ni1 S23 87.02(4) . . ? C2 O1 Ni1 123.8(3) . . ? O1 C2 C11 124.0(4) . . ? O1 C2 C3 117.4(4) . . ? C11 C2 C3 118.6(4) . . ? C4 C3 C2 122.4(4) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C10 120.4(4) . . ? C6 C5 C4 120.5(5) . . ? C10 C5 C4 119.0(4) . . ? C7 C6 C5 120.8(5) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.3(4) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 121.7(5) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 120.1(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 117.8(4) . . ? C5 C10 C11 119.8(4) . . ? C9 C10 C11 122.4(4) . . ? C2 C11 C12 122.1(4) . . ? C2 C11 C10 119.0(4) . . ? C12 C11 C10 118.7(4) . . ? N13 C12 C11 127.4(4) . . ? N13 C12 H12 116.3 . . ? C11 C12 H12 116.3 . . ? C12 N13 C14 118.4(3) . . ? C12 N13 Ni1 120.4(3) . . ? C14 N13 Ni1 119.5(3) . . ? C15 C14 C19 118.4(4) . . ? C15 C14 N13 123.3(4) . . ? C19 C14 N13 118.3(4) . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 121.5(4) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 118.2(4) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C19 C18 C17 120.7(4) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C14 120.8(4) . . ? C18 C19 S20 119.4(3) . . ? C14 C19 S20 119.8(3) . . ? C19 S20 C21 99.0(2) . . ? C19 S20 Ni1 96.29(15) . . ? C21 S20 Ni1 102.31(15) . . ? C22 C21 S20 112.8(3) . . ? C22 C21 H21A 109.0 . . ? S20 C21 H21A 109.0 . . ? C22 C21 H21B 109.0 . . ? S20 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 S23 113.4(3) . . ? C21 C22 H22A 108.9 . . ? S23 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? S23 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C24 S23 C22 99.2(2) . . ? C24 S23 Ni1 96.02(13) . . ? C22 S23 Ni1 101.18(13) . . ? C25 C24 C29 120.3(4) . . ? C25 C24 S23 119.7(3) . . ? C29 C24 S23 119.9(3) . . ? C26 C25 C24 120.3(4) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C27 C26 C25 119.9(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.5(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 120.3(4) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C24 118.5(4) . . ? C28 C29 N30 123.1(4) . . ? C24 C29 N30 118.4(4) . . ? C31 N30 C29 118.3(3) . . ? C31 N30 Ni1 119.9(3) . . ? C29 N30 Ni1 120.2(3) . . ? N30 C31 C32 127.9(4) . . ? N30 C31 H31 116.0 . . ? C32 C31 H31 116.0 . . ? C31 C32 C41 120.9(4) . . ? C31 C32 C33 119.0(4) . . ? C41 C32 C33 120.0(4) . . ? C34 C33 C38 115.4(5) . . ? C34 C33 C32 124.0(4) . . ? C38 C33 C32 120.6(4) . . ? C35 C34 C33 122.5(4) . . ? C35 C34 H34 118.7 . . ? C33 C34 H34 118.7 . . ? C34 C35 C36 120.9(5) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C37 C36 C35 118.4(5) . . ? C37 C36 H36 120.8 . . ? C35 C36 H36 120.8 . . ? C36 C37 C38 121.9(4) . . ? C36 C37 H37 119.1 . . ? C38 C37 H37 119.1 . . ? C37 C38 C33 120.8(5) . . ? C37 C38 C39 122.0(4) . . ? C33 C38 C39 117.2(5) . . ? C40 C39 C38 122.6(4) . . ? C40 C39 H39 118.7 . . ? C38 C39 H39 118.7 . . ? C39 C40 C41 122.1(4) . . ? C39 C40 H40 119.0 . . ? C41 C40 H40 119.0 . . ? O42 C41 C32 124.9(4) . . ? O42 C41 C40 118.0(4) . . ? C32 C41 C40 117.1(4) . . ? C41 O42 Ni1 121.7(3) . . ? O1S C1S H1S1 109.5 . . ? O1S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? O1S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? C1S O1S H1S 130(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 O42 Ni1 O1 C2 52.6(3) . . . . ? N30 Ni1 O1 C2 141.0(3) . . . . ? N13 Ni1 O1 C2 -36.8(3) . . . . ? S20 Ni1 O1 C2 -63.7(7) . . . . ? S23 Ni1 O1 C2 -136.0(3) . . . . ? Ni1 O1 C2 C11 21.0(6) . . . . ? Ni1 O1 C2 C3 -160.3(3) . . . . ? O1 C2 C3 C4 180.0(4) . . . . ? C11 C2 C3 C4 -1.3(7) . . . . ? C2 C3 C4 C5 -2.2(7) . . . . ? C3 C4 C5 C6 -176.5(4) . . . . ? C3 C4 C5 C10 0.4(7) . . . . ? C10 C5 C6 C7 -0.1(7) . . . . ? C4 C5 C6 C7 176.9(5) . . . . ? C5 C6 C7 C8 -1.5(7) . . . . ? C6 C7 C8 C9 1.3(8) . . . . ? C7 C8 C9 C10 0.5(8) . . . . ? C6 C5 C10 C9 1.8(6) . . . . ? C4 C5 C10 C9 -175.1(4) . . . . ? C6 C5 C10 C11 -178.2(4) . . . . ? C4 C5 C10 C11 4.8(6) . . . . ? C8 C9 C10 C5 -2.0(7) . . . . ? C8 C9 C10 C11 178.0(4) . . . . ? O1 C2 C11 C12 10.0(7) . . . . ? C3 C2 C11 C12 -168.6(4) . . . . ? O1 C2 C11 C10 -174.9(4) . . . . ? C3 C2 C11 C10 6.5(6) . . . . ? C5 C10 C11 C2 -8.3(6) . . . . ? C9 C10 C11 C2 171.7(4) . . . . ? C5 C10 C11 C12 167.0(4) . . . . ? C9 C10 C11 C12 -13.1(6) . . . . ? C2 C11 C12 N13 -10.9(7) . . . . ? C10 C11 C12 N13 174.0(4) . . . . ? C11 C12 N13 C14 176.1(4) . . . . ? C11 C12 N13 Ni1 -18.6(6) . . . . ? O42 Ni1 N13 C12 -59.2(3) . . . . ? O1 Ni1 N13 C12 34.5(3) . . . . ? N30 Ni1 N13 C12 -23(3) . . . . ? S20 Ni1 N13 C12 -149.7(3) . . . . ? S23 Ni1 N13 C12 124.4(3) . . . . ? O42 Ni1 N13 C14 105.9(3) . . . . ? O1 Ni1 N13 C14 -160.4(3) . . . . ? N30 Ni1 N13 C14 142(3) . . . . ? S20 Ni1 N13 C14 15.5(3) . . . . ? S23 Ni1 N13 C14 -70.4(3) . . . . ? C12 N13 C14 C15 -30.7(5) . . . . ? Ni1 N13 C14 C15 163.9(3) . . . . ? C12 N13 C14 C19 151.0(4) . . . . ? Ni1 N13 C14 C19 -14.4(5) . . . . ? C19 C14 C15 C16 -4.2(6) . . . . ? N13 C14 C15 C16 177.5(4) . . . . ? C14 C15 C16 C17 0.7(6) . . . . ? C15 C16 C17 C18 2.0(6) . . . . ? C16 C17 C18 C19 -1.3(6) . . . . ? C17 C18 C19 C14 -2.2(6) . . . . ? C17 C18 C19 S20 179.4(3) . . . . ? C15 C14 C19 C18 4.9(6) . . . . ? N13 C14 C19 C18 -176.7(3) . . . . ? C15 C14 C19 S20 -176.7(3) . . . . ? N13 C14 C19 S20 1.7(5) . . . . ? C18 C19 S20 C21 -69.6(4) . . . . ? C14 C19 S20 C21 112.0(3) . . . . ? C18 C19 S20 Ni1 -173.2(3) . . . . ? C14 C19 S20 Ni1 8.5(3) . . . . ? O42 Ni1 S20 C19 -100.68(16) . . . . ? O1 Ni1 S20 C19 15.8(5) . . . . ? N30 Ni1 S20 C19 170.83(16) . . . . ? N13 Ni1 S20 C19 -11.24(16) . . . . ? S23 Ni1 S20 C19 88.34(13) . . . . ? O42 Ni1 S20 C21 158.67(17) . . . . ? O1 Ni1 S20 C21 -84.8(5) . . . . ? N30 Ni1 S20 C21 70.18(17) . . . . ? N13 Ni1 S20 C21 -111.89(17) . . . . ? S23 Ni1 S20 C21 -12.31(15) . . . . ? C19 S20 C21 C22 -57.6(4) . . . . ? Ni1 S20 C21 C22 41.0(3) . . . . ? S20 C21 C22 S23 -57.1(4) . . . . ? C21 C22 S23 C24 -58.0(3) . . . . ? C21 C22 S23 Ni1 40.1(3) . . . . ? O42 Ni1 S23 C24 15.5(6) . . . . ? O1 Ni1 S23 C24 -99.14(17) . . . . ? N30 Ni1 S23 C24 -8.88(18) . . . . ? N13 Ni1 S23 C24 172.52(18) . . . . ? S20 Ni1 S23 C24 89.54(15) . . . . ? O42 Ni1 S23 C22 -85.2(6) . . . . ? O1 Ni1 S23 C22 160.21(17) . . . . ? N30 Ni1 S23 C22 -109.54(18) . . . . ? N13 Ni1 S23 C22 71.86(18) . . . . ? S20 Ni1 S23 C22 -11.12(15) . . . . ? C22 S23 C24 C25 -71.7(4) . . . . ? Ni1 S23 C24 C25 -174.1(4) . . . . ? C22 S23 C24 C29 106.0(4) . . . . ? Ni1 S23 C24 C29 3.6(4) . . . . ? C29 C24 C25 C26 -1.3(7) . . . . ? S23 C24 C25 C26 176.4(4) . . . . ? C24 C25 C26 C27 -1.6(7) . . . . ? C25 C26 C27 C28 2.3(7) . . . . ? C26 C27 C28 C29 -0.1(7) . . . . ? C27 C28 C29 C24 -2.6(6) . . . . ? C27 C28 C29 N30 175.6(4) . . . . ? C25 C24 C29 C28 3.3(6) . . . . ? S23 C24 C29 C28 -174.3(3) . . . . ? C25 C24 C29 N30 -175.0(4) . . . . ? S23 C24 C29 N30 7.3(6) . . . . ? C28 C29 N30 C31 -30.4(6) . . . . ? C24 C29 N30 C31 147.8(4) . . . . ? C28 C29 N30 Ni1 164.1(3) . . . . ? C24 C29 N30 Ni1 -17.7(5) . . . . ? O42 Ni1 N30 C31 34.0(3) . . . . ? O1 Ni1 N30 C31 -59.7(3) . . . . ? N13 Ni1 N30 C31 -3(3) . . . . ? S20 Ni1 N30 C31 124.1(3) . . . . ? S23 Ni1 N30 C31 -149.9(3) . . . . ? O42 Ni1 N30 C29 -160.8(3) . . . . ? O1 Ni1 N30 C29 105.6(3) . . . . ? N13 Ni1 N30 C29 163(3) . . . . ? S20 Ni1 N30 C29 -70.6(3) . . . . ? S23 Ni1 N30 C29 15.4(3) . . . . ? C29 N30 C31 C32 -179.5(4) . . . . ? Ni1 N30 C31 C32 -13.9(6) . . . . ? N30 C31 C32 C41 -14.9(7) . . . . ? N30 C31 C32 C33 167.2(4) . . . . ? C31 C32 C33 C34 -10.5(6) . . . . ? C41 C32 C33 C34 171.5(4) . . . . ? C31 C32 C33 C38 171.1(4) . . . . ? C41 C32 C33 C38 -6.9(6) . . . . ? C38 C33 C34 C35 -3.3(7) . . . . ? C32 C33 C34 C35 178.3(4) . . . . ? C33 C34 C35 C36 0.7(7) . . . . ? C34 C35 C36 C37 1.8(7) . . . . ? C35 C36 C37 C38 -1.6(7) . . . . ? C36 C37 C38 C33 -1.1(7) . . . . ? C36 C37 C38 C39 178.4(4) . . . . ? C34 C33 C38 C37 3.4(6) . . . . ? C32 C33 C38 C37 -178.1(4) . . . . ? C34 C33 C38 C39 -176.1(4) . . . . ? C32 C33 C38 C39 2.4(6) . . . . ? C37 C38 C39 C40 -177.7(4) . . . . ? C33 C38 C39 C40 1.8(6) . . . . ? C38 C39 C40 C41 -1.6(7) . . . . ? C31 C32 C41 O42 7.7(7) . . . . ? C33 C32 C41 O42 -174.4(4) . . . . ? C31 C32 C41 C40 -171.0(4) . . . . ? C33 C32 C41 C40 7.0(6) . . . . ? C39 C40 C41 O42 178.4(4) . . . . ? C39 C40 C41 C32 -2.9(6) . . . . ? C32 C41 O42 Ni1 27.1(5) . . . . ? C40 C41 O42 Ni1 -154.2(3) . . . . ? O1 Ni1 O42 C41 49.0(3) . . . . ? N30 Ni1 O42 C41 -41.1(3) . . . . ? N13 Ni1 O42 C41 137.3(3) . . . . ? S20 Ni1 O42 C41 -139.1(3) . . . . ? S23 Ni1 O42 C41 -65.3(7) . . . . ? 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 O1S H1S O1 0.840(10) 1.94(4) 2.759(7) 163(14) 2_666 _diffrn_measured_fraction_theta_max 0.780 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.780 _refine_diff_density_max 0.422 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.077 data_rao003 _database_code_CSD 216931 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H26 N2 O2 S2 Zn' _chemical_formula_weight 648.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.994(1) _cell_length_b 7.612(1) _cell_length_c 17.980(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.55(1) _cell_angle_gamma 90.00 _cell_volume 2946.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2505 _cell_measurement_theta_min 7 _cell_measurement_theta_max 25 _exptl_crystal_description Rods _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 30 mm; 20 sec./deg.; 1 deg; 2 sets; 212 frames ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4626 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2501 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (A.L.Spek, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0150P)^2^+4.6217P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2501 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.72129(5) 0.2500 0.02371(14) Uani 1 2 d S . . O1 O 0.52479(8) 0.8831(2) 0.18029(11) 0.0283(4) Uani 1 1 d . . . C2 C 0.57501(12) 0.8745(3) 0.16439(15) 0.0239(6) Uani 1 1 d . . . C3 C 0.57444(13) 0.9625(3) 0.09326(16) 0.0310(7) Uani 1 1 d . . . H3A H 0.5392 1.0246 0.0632 0.037 Uiso 1 1 calc R . . C4 C 0.62375(14) 0.9573(4) 0.06907(17) 0.0333(7) Uani 1 1 d . . . H4A H 0.6208 1.0116 0.0215 0.040 Uiso 1 1 calc R . . C5 C 0.68007(13) 0.8716(3) 0.11395(16) 0.0288(6) Uani 1 1 d . . . C6 C 0.73098(14) 0.8682(4) 0.08759(18) 0.0358(7) Uani 1 1 d . . . H6A H 0.7274 0.9226 0.0399 0.043 Uiso 1 1 calc R . . C7 C 0.78546(14) 0.7871(4) 0.13018(18) 0.0386(7) Uani 1 1 d . . . H7A H 0.8187 0.7870 0.1120 0.046 Uiso 1 1 calc R . . C8 C 0.79043(13) 0.7043(4) 0.20155(18) 0.0365(7) Uani 1 1 d . . . H8A H 0.8273 0.6487 0.2311 0.044 Uiso 1 1 calc R . . C9 C 0.74137(12) 0.7041(3) 0.22866(16) 0.0295(6) Uani 1 1 d . . . H9A H 0.7457 0.6468 0.2760 0.035 Uiso 1 1 calc R . . C10 C 0.68460(12) 0.7884(3) 0.18663(15) 0.0234(6) Uani 1 1 d . . . C11 C 0.63112(11) 0.7885(3) 0.21228(14) 0.0213(6) Uani 1 1 d . . . C12 C 0.63705(12) 0.7144(3) 0.28751(14) 0.0222(6) Uani 1 1 d . . . H12A H 0.6768 0.6803 0.3194 0.027 Uiso 1 1 calc R . . N13 N 0.59334(9) 0.6889(3) 0.31673(12) 0.0217(5) Uani 1 1 d . . . C14 C 0.60972(12) 0.6343(3) 0.39710(15) 0.0235(6) Uani 1 1 d . . . C15 C 0.66303(13) 0.6939(4) 0.45639(16) 0.0315(7) Uani 1 1 d . . . H15A H 0.6908 0.7652 0.4433 0.038 Uiso 1 1 calc R . . C16 C 0.67516(14) 0.6477(4) 0.53532(17) 0.0359(7) Uani 1 1 d . . . H16A H 0.7115 0.6863 0.5744 0.043 Uiso 1 1 calc R . . C17 C 0.63397(15) 0.5457(4) 0.55587(18) 0.0392(8) Uani 1 1 d . . . H17A H 0.6416 0.5184 0.6089 0.047 Uiso 1 1 calc R . . C18 C 0.58130(14) 0.4838(4) 0.49761(17) 0.0356(7) Uani 1 1 d . . . H18A H 0.5539 0.4127 0.5116 0.043 Uiso 1 1 calc R . . C19 C 0.56852(12) 0.5259(3) 0.41853(16) 0.0268(6) Uani 1 1 d . . . S20 S 0.49789(3) 0.45315(9) 0.34664(4) 0.03102(19) Uani 1 1 d . . . C21 C 0.52174(13) 0.2794(4) 0.29316(17) 0.0362(7) Uani 1 1 d . . . H21A H 0.5641 0.2995 0.2959 0.043 Uiso 1 1 calc R . . H21B H 0.5201 0.1664 0.3172 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0202(3) 0.0204(2) 0.0311(3) 0.000 0.00978(19) 0.000 O1 0.0238(11) 0.0247(10) 0.0375(12) 0.0077(8) 0.0122(9) 0.0038(8) C2 0.0270(16) 0.0171(13) 0.0273(15) -0.0020(11) 0.0092(12) -0.0049(11) C3 0.0275(16) 0.0299(16) 0.0301(16) 0.0075(12) 0.0033(13) -0.0011(12) C4 0.0383(19) 0.0329(17) 0.0267(16) 0.0076(12) 0.0088(14) -0.0059(13) C5 0.0360(17) 0.0239(15) 0.0287(16) -0.0025(12) 0.0142(13) -0.0103(12) C6 0.0401(19) 0.0372(17) 0.0362(18) 0.0023(14) 0.0212(15) -0.0086(14) C7 0.0372(18) 0.0402(17) 0.0496(19) 0.0002(15) 0.0292(16) -0.0053(15) C8 0.0285(16) 0.0394(17) 0.0461(19) 0.0079(14) 0.0186(14) 0.0043(13) C9 0.0305(16) 0.0292(15) 0.0313(16) 0.0043(13) 0.0140(13) -0.0010(13) C10 0.0262(15) 0.0199(13) 0.0245(14) -0.0015(11) 0.0095(12) -0.0069(11) C11 0.0230(14) 0.0181(13) 0.0239(14) 0.0002(11) 0.0098(11) -0.0026(11) C12 0.0218(14) 0.0182(13) 0.0256(14) -0.0009(11) 0.0071(12) 0.0004(11) N13 0.0221(12) 0.0209(12) 0.0233(12) 0.0016(9) 0.0096(10) 0.0013(9) C14 0.0257(15) 0.0221(14) 0.0238(15) 0.0031(11) 0.0101(12) 0.0065(11) C15 0.0286(16) 0.0359(17) 0.0313(16) -0.0019(13) 0.0121(13) 0.0011(13) C16 0.0323(18) 0.0472(18) 0.0257(16) -0.0018(13) 0.0068(14) 0.0075(14) C17 0.050(2) 0.0414(18) 0.0281(17) 0.0125(14) 0.0162(16) 0.0166(15) C18 0.043(2) 0.0328(17) 0.0387(18) 0.0122(13) 0.0237(16) 0.0094(14) C19 0.0278(16) 0.0253(15) 0.0305(16) 0.0049(12) 0.0143(13) 0.0066(12) S20 0.0273(4) 0.0282(4) 0.0419(5) 0.0060(3) 0.0176(3) -0.0008(3) C21 0.0358(17) 0.0177(15) 0.0534(19) 0.0041(13) 0.0136(14) 0.0020(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9784(17) 2_655 ? Zn1 O1 1.9784(17) . ? Zn1 N13 2.073(2) 2_655 ? Zn1 N13 2.073(2) . ? Zn1 S20 2.6919(8) 2_655 ? Zn1 S20 2.6919(8) . ? O1 C2 1.285(3) . ? C2 C11 1.433(4) . ? C2 C3 1.440(4) . ? C3 C4 1.350(4) . ? C3 H3A 0.9300 . ? C4 C5 1.421(4) . ? C4 H4A 0.9300 . ? C5 C6 1.409(4) . ? C5 C10 1.423(3) . ? C6 C7 1.365(4) . ? C6 H6A 0.9300 . ? C7 C8 1.398(4) . ? C7 H7A 0.9300 . ? C8 C9 1.377(4) . ? C8 H8A 0.9300 . ? C9 C10 1.412(4) . ? C9 H9A 0.9300 . ? C10 C11 1.457(3) . ? C11 C12 1.427(3) . ? C12 N13 1.302(3) . ? C12 H12A 0.9300 . ? N13 C14 1.421(3) . ? C14 C15 1.388(4) . ? C14 C19 1.409(4) . ? C15 C16 1.392(4) . ? C15 H15A 0.9300 . ? C16 C17 1.372(4) . ? C16 H16A 0.9300 . ? C17 C18 1.377(4) . ? C17 H17A 0.9300 . ? C18 C19 1.385(4) . ? C18 H18A 0.9300 . ? C19 S20 1.772(3) . ? S20 C21 1.829(3) . ? C21 C21 1.523(6) 2_655 ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 103.01(11) 2_655 . ? O1 Zn1 N13 88.33(8) 2_655 2_655 ? O1 Zn1 N13 100.22(8) . 2_655 ? O1 Zn1 N13 100.22(8) 2_655 . ? O1 Zn1 N13 88.33(8) . . ? N13 Zn1 N13 166.33(11) 2_655 . ? O1 Zn1 S20 162.82(5) 2_655 2_655 ? O1 Zn1 S20 89.35(6) . 2_655 ? N13 Zn1 S20 77.63(6) 2_655 2_655 ? N13 Zn1 S20 91.94(6) . 2_655 ? O1 Zn1 S20 89.35(6) 2_655 . ? O1 Zn1 S20 162.82(5) . . ? N13 Zn1 S20 91.94(6) 2_655 . ? N13 Zn1 S20 77.63(6) . . ? S20 Zn1 S20 81.38(3) 2_655 . ? C2 O1 Zn1 126.20(16) . . ? O1 C2 C11 125.4(2) . . ? O1 C2 C3 116.4(2) . . ? C11 C2 C3 118.2(2) . . ? C4 C3 C2 121.7(3) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C3 C4 C5 122.1(3) . . ? C3 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 C10 119.9(3) . . ? C4 C5 C10 119.0(2) . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 118.8(3) . . ? C6 C7 H7A 120.6 . . ? C8 C7 H7A 120.6 . . ? C9 C8 C7 120.8(3) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C8 C9 C10 121.9(2) . . ? C8 C9 H9A 119.1 . . ? C10 C9 H9A 119.1 . . ? C9 C10 C5 116.7(2) . . ? C9 C10 C11 123.7(2) . . ? C5 C10 C11 119.5(2) . . ? C12 C11 C2 121.1(2) . . ? C12 C11 C10 119.3(2) . . ? C2 C11 C10 119.5(2) . . ? N13 C12 C11 127.7(2) . . ? N13 C12 H12A 116.2 . . ? C11 C12 H12A 116.2 . . ? C12 N13 C14 119.2(2) . . ? C12 N13 Zn1 122.52(17) . . ? C14 N13 Zn1 118.31(16) . . ? C15 C14 C19 118.6(2) . . ? C15 C14 N13 122.2(2) . . ? C19 C14 N13 119.0(2) . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C17 C18 C19 121.0(3) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C18 C19 C14 119.7(3) . . ? C18 C19 S20 119.1(2) . . ? C14 C19 S20 121.0(2) . . ? C19 S20 C21 104.02(13) . . ? C19 S20 Zn1 90.83(9) . . ? C21 S20 Zn1 97.60(9) . . ? C21 C21 S20 108.97(18) 2_655 . ? C21 C21 H21A 109.9 2_655 . ? S20 C21 H21A 109.9 . . ? C21 C21 H21B 109.9 2_655 . ? S20 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Zn1 O1 C2 131.5(2) 2_655 . . . ? N13 Zn1 O1 C2 -137.9(2) 2_655 . . . ? N13 Zn1 O1 C2 31.4(2) . . . . ? S20 Zn1 O1 C2 -60.6(2) 2_655 . . . ? S20 Zn1 O1 C2 -3.5(4) . . . . ? Zn1 O1 C2 C11 -22.4(4) . . . . ? Zn1 O1 C2 C3 159.03(18) . . . . ? O1 C2 C3 C4 -177.7(2) . . . . ? C11 C2 C3 C4 3.7(4) . . . . ? C2 C3 C4 C5 -2.9(4) . . . . ? C3 C4 C5 C6 -179.9(3) . . . . ? C3 C4 C5 C10 0.1(4) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? C10 C5 C6 C7 -0.3(4) . . . . ? C5 C6 C7 C8 0.5(5) . . . . ? C6 C7 C8 C9 0.0(5) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? C8 C9 C10 C5 0.9(4) . . . . ? C8 C9 C10 C11 178.7(3) . . . . ? C6 C5 C10 C9 -0.4(4) . . . . ? C4 C5 C10 C9 179.6(2) . . . . ? C6 C5 C10 C11 -178.3(2) . . . . ? C4 C5 C10 C11 1.7(4) . . . . ? O1 C2 C11 C12 -5.1(4) . . . . ? C3 C2 C11 C12 173.5(2) . . . . ? O1 C2 C11 C10 179.7(2) . . . . ? C3 C2 C11 C10 -1.8(4) . . . . ? C9 C10 C11 C12 6.1(4) . . . . ? C5 C10 C11 C12 -176.2(2) . . . . ? C9 C10 C11 C2 -178.5(2) . . . . ? C5 C10 C11 C2 -0.8(4) . . . . ? C2 C11 C12 N13 11.5(4) . . . . ? C10 C11 C12 N13 -173.3(2) . . . . ? C11 C12 N13 C14 -171.9(2) . . . . ? C11 C12 N13 Zn1 9.0(4) . . . . ? O1 Zn1 N13 C12 -127.26(19) 2_655 . . . ? O1 Zn1 N13 C12 -24.35(19) . . . . ? N13 Zn1 N13 C12 104.75(19) 2_655 . . . ? S20 Zn1 N13 C12 64.94(19) 2_655 . . . ? S20 Zn1 N13 C12 145.68(19) . . . . ? O1 Zn1 N13 C14 53.62(18) 2_655 . . . ? O1 Zn1 N13 C14 156.54(18) . . . . ? N13 Zn1 N13 C14 -74.36(17) 2_655 . . . ? S20 Zn1 N13 C14 -114.17(17) 2_655 . . . ? S20 Zn1 N13 C14 -33.43(16) . . . . ? C12 N13 C14 C15 36.1(4) . . . . ? Zn1 N13 C14 C15 -144.8(2) . . . . ? C12 N13 C14 C19 -148.4(2) . . . . ? Zn1 N13 C14 C19 30.8(3) . . . . ? C19 C14 C15 C16 -0.3(4) . . . . ? N13 C14 C15 C16 175.3(2) . . . . ? C14 C15 C16 C17 -1.4(4) . . . . ? C15 C16 C17 C18 2.2(4) . . . . ? C16 C17 C18 C19 -1.3(4) . . . . ? C17 C18 C19 C14 -0.3(4) . . . . ? C17 C18 C19 S20 -176.4(2) . . . . ? C15 C14 C19 C18 1.1(4) . . . . ? N13 C14 C19 C18 -174.6(2) . . . . ? C15 C14 C19 S20 177.1(2) . . . . ? N13 C14 C19 S20 1.4(3) . . . . ? C18 C19 S20 C21 -107.9(2) . . . . ? C14 C19 S20 C21 76.1(2) . . . . ? C18 C19 S20 Zn1 154.1(2) . . . . ? C14 C19 S20 Zn1 -21.9(2) . . . . ? O1 Zn1 S20 C19 -74.79(10) 2_655 . . . ? O1 Zn1 S20 C19 61.7(2) . . . . ? N13 Zn1 S20 C19 -163.09(10) 2_655 . . . ? N13 Zn1 S20 C19 25.82(10) . . . . ? S20 Zn1 S20 C19 119.73(9) 2_655 . . . ? O1 Zn1 S20 C21 -179.05(10) 2_655 . . . ? O1 Zn1 S20 C21 -42.6(2) . . . . ? N13 Zn1 S20 C21 92.65(11) 2_655 . . . ? N13 Zn1 S20 C21 -78.44(11) . . . . ? S20 Zn1 S20 C21 15.47(9) 2_655 . . . ? C19 S20 C21 C21 -147.1(2) . . . 2_655 ? Zn1 S20 C21 C21 -54.3(2) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.265 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.058 data_importt _database_code_CSD 216932 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Co0.50 N O4' _chemical_formula_weight 314.75 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P42/n _symmetry_Int_Tables_number 86 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 13.9290(3) _cell_length_b 13.9290(3) _cell_length_c 14.2310(5) _cell_angle_alpha 90.000(1) _cell_angle_beta 90.000(1) _cell_angle_gamma 90.000(2) _cell_volume 2761.06(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9392 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.682 _exptl_crystal_description Red _exptl_crystal_colour Prisms _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.680 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 30 mm; 40 sec./deg.; 2 deg.; 4 sets; 149 frames; mos. 0.447(13) deg. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 0.5 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17104 _diffrn_reflns_av_R_equivalents 0.1015 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.70 _reflns_number_total 2620 _reflns_number_gt 1839 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0393P)^2^+3.5336P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2620 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.8389(2) 0.4082(2) 0.1493(2) 0.0208(7) Uani 1 1 d . . . C3 C 0.9033(2) 0.4669(2) 0.1007(2) 0.0258(7) Uani 1 1 d . . . H3 H 0.9580 0.4391 0.0717 0.031 Uiso 1 1 calc R . . C4 C 0.8886(2) 0.5648(2) 0.0943(2) 0.0297(8) Uani 1 1 d . . . H4 H 0.9331 0.6035 0.0608 0.036 Uiso 1 1 calc R . . C5 C 0.8096(2) 0.6066(2) 0.1364(2) 0.0300(8) Uani 1 1 d . . . H5 H 0.8005 0.6741 0.1326 0.036 Uiso 1 1 calc R . . C6 C 0.7442(2) 0.5508(2) 0.1838(2) 0.0261(7) Uani 1 1 d . . . H6 H 0.6899 0.5798 0.2126 0.031 Uiso 1 1 calc R . . C7 C 0.7572(2) 0.4521(2) 0.1896(2) 0.0204(7) Uani 1 1 d . . . C9 C 0.6071(2) 0.4103(2) 0.2542(2) 0.0232(7) Uani 1 1 d . . . H9 H 0.5861 0.4724 0.2359 0.028 Uiso 1 1 calc R . . C10 C 0.5378(2) 0.3480(2) 0.3011(2) 0.0226(7) Uani 1 1 d . . . C11 C 0.4410(2) 0.3759(2) 0.2965(2) 0.0276(8) Uani 1 1 d . . . H11 H 0.4238 0.4326 0.2634 0.033 Uiso 1 1 calc R . . C12 C 0.3707(2) 0.3218(3) 0.3395(2) 0.0324(8) Uani 1 1 d . . . H12 H 0.3054 0.3411 0.3351 0.039 Uiso 1 1 calc R . . C13 C 0.3942(2) 0.2403(3) 0.3884(2) 0.0323(8) Uani 1 1 d . . . H13 H 0.3453 0.2039 0.4184 0.039 Uiso 1 1 calc R . . C14 C 0.4893(2) 0.2110(2) 0.3942(2) 0.0277(8) Uani 1 1 d . . . H14 H 0.5057 0.1546 0.4281 0.033 Uiso 1 1 calc R . . C15 C 0.5597(2) 0.2640(2) 0.3506(2) 0.0205(7) Uani 1 1 d . . . C17 C 0.6993(2) 0.2674(2) 0.4442(2) 0.0225(7) Uani 1 1 d . . . H17A H 0.6647 0.2424 0.4998 0.027 Uiso 1 1 calc R . . H17B H 0.6976 0.3384 0.4460 0.027 Uiso 1 1 calc R . . C20 C 0.5185(3) 0.3360(3) 0.0160(3) 0.0353(8) Uani 1 1 d . . . C21 C 0.4602(3) 0.3548(3) -0.0670(3) 0.0570(12) Uani 1 1 d . . . H21A H 0.4429 0.4230 -0.0689 0.085 Uiso 1 1 calc R . . H21B H 0.4017 0.3159 -0.0644 0.085 Uiso 1 1 calc R . . H21C H 0.4968 0.3382 -0.1235 0.085 Uiso 1 1 calc R . . N8 N 0.69413(17) 0.38740(17) 0.23573(18) 0.0193(6) Uani 1 1 d . . . O1 O 0.85171(14) 0.31338(14) 0.15682(14) 0.0217(5) Uani 1 1 d . . . O16 O 0.65470(13) 0.23269(14) 0.35878(14) 0.0195(5) Uani 1 1 d . . . O19 O 0.51294(19) 0.24714(19) 0.0471(2) 0.0455(7) Uani 1 1 d D . . H19 H 0.556(2) 0.238(3) 0.087(2) 0.068 Uiso 1 1 d D . . O22 O 0.5701(2) 0.3945(2) 0.0524(2) 0.0634(9) Uani 1 1 d . . . Co18 Co 0.7500 0.2500 0.23515(4) 0.01753(17) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0224(16) 0.0215(16) 0.0186(17) -0.0008(13) -0.0042(13) -0.0008(13) C3 0.0231(16) 0.0298(18) 0.0245(19) -0.0009(14) 0.0031(14) -0.0028(14) C4 0.0324(19) 0.0277(18) 0.029(2) 0.0048(14) 0.0034(15) -0.0082(15) C5 0.040(2) 0.0194(16) 0.030(2) 0.0009(14) -0.0024(16) -0.0028(15) C6 0.0293(17) 0.0230(16) 0.0260(19) -0.0034(14) 0.0002(14) 0.0027(14) C7 0.0222(16) 0.0226(16) 0.0163(17) 0.0001(12) -0.0014(13) -0.0043(13) C9 0.0258(17) 0.0225(16) 0.0213(18) -0.0016(13) -0.0015(13) 0.0021(13) C10 0.0205(16) 0.0256(17) 0.0217(17) -0.0055(13) 0.0015(13) -0.0019(13) C11 0.0235(17) 0.0297(18) 0.029(2) -0.0036(14) -0.0015(14) 0.0035(14) C12 0.0175(16) 0.045(2) 0.035(2) -0.0092(17) -0.0025(15) 0.0017(15) C13 0.0189(17) 0.046(2) 0.032(2) -0.0030(16) 0.0015(15) -0.0077(16) C14 0.0261(17) 0.0319(18) 0.025(2) 0.0000(15) -0.0014(14) -0.0051(15) C15 0.0164(15) 0.0268(16) 0.0183(17) -0.0080(13) -0.0007(12) -0.0002(13) C17 0.0213(16) 0.0319(17) 0.0142(16) -0.0043(14) -0.0018(13) -0.0043(14) C20 0.0331(19) 0.0302(19) 0.043(2) -0.0025(17) 0.0032(17) -0.0020(16) C21 0.059(3) 0.054(3) 0.058(3) -0.004(2) -0.012(2) 0.006(2) N8 0.0193(13) 0.0222(13) 0.0163(14) -0.0021(11) 0.0003(10) 0.0005(11) O1 0.0239(11) 0.0198(11) 0.0215(12) 0.0035(9) 0.0037(9) 0.0030(9) O16 0.0161(10) 0.0274(11) 0.0150(11) -0.0030(9) -0.0010(8) 0.0011(9) O19 0.0469(17) 0.0368(15) 0.0528(19) 0.0054(13) -0.0184(13) -0.0053(13) O22 0.079(2) 0.0560(19) 0.056(2) 0.0034(16) -0.0171(18) -0.0101(18) Co18 0.0188(3) 0.0189(3) 0.0149(3) 0.000 0.000 0.0011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O1 1.338(3) . ? C2 C3 1.396(4) . ? C2 C7 1.413(4) . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 H4 0.9500 . ? C5 C6 1.375(5) . ? C5 H5 0.9500 . ? C6 C7 1.388(4) . ? C6 H6 0.9500 . ? C7 N8 1.420(4) . ? C9 N8 1.281(4) . ? C9 C10 1.460(4) . ? C9 H9 0.9500 . ? C10 C15 1.399(4) . ? C10 C11 1.405(4) . ? C11 C12 1.379(5) . ? C11 H11 0.9500 . ? C12 C13 1.371(5) . ? C12 H12 0.9500 . ? C13 C14 1.389(4) . ? C13 H13 0.9500 . ? C14 C15 1.375(4) . ? C14 H14 0.9500 . ? C15 O16 1.399(3) . ? C17 O16 1.448(3) . ? C17 C17 1.493(6) 2_655 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C20 O22 1.204(4) . ? C20 O19 1.317(4) . ? C20 C21 1.457(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N8 Co18 2.066(2) . ? O1 Co18 2.007(2) . ? O16 Co18 2.217(2) . ? O19 H19 0.841(3) . ? Co18 O1 2.007(2) 2_655 ? Co18 N8 2.066(2) 2_655 ? Co18 O16 2.217(2) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 C3 122.1(3) . . ? O1 C2 C7 120.2(3) . . ? C3 C2 C7 117.7(3) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.1(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 N8 125.1(3) . . ? C2 C7 N8 114.3(3) . . ? N8 C9 C10 124.9(3) . . ? N8 C9 H9 117.6 . . ? C10 C9 H9 117.6 . . ? C15 C10 C11 117.6(3) . . ? C15 C10 C9 125.7(3) . . ? C11 C10 C9 116.7(3) . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 O16 118.0(3) . . ? C14 C15 C10 121.4(3) . . ? O16 C15 C10 120.6(3) . . ? O16 C17 C17 107.3(2) . 2_655 ? O16 C17 H17A 110.3 . . ? C17 C17 H17A 110.3 2_655 . ? O16 C17 H17B 110.3 . . ? C17 C17 H17B 110.3 2_655 . ? H17A C17 H17B 108.5 . . ? O22 C20 O19 121.8(4) . . ? O22 C20 C21 124.1(4) . . ? O19 C20 C21 114.1(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C9 N8 C7 121.5(3) . . ? C9 N8 Co18 126.0(2) . . ? C7 N8 Co18 110.69(18) . . ? C2 O1 Co18 112.61(17) . . ? C15 O16 C17 111.8(2) . . ? C15 O16 Co18 117.80(17) . . ? C17 O16 Co18 111.89(16) . . ? C20 O19 H19 110(3) . . ? O1 Co18 O1 112.53(12) 2_655 . ? O1 Co18 N8 81.99(9) 2_655 2_655 ? O1 Co18 N8 98.26(9) . 2_655 ? O1 Co18 N8 98.26(9) 2_655 . ? O1 Co18 N8 81.99(9) . . ? N8 Co18 N8 179.54(14) 2_655 . ? O1 Co18 O16 155.66(8) 2_655 2_655 ? O1 Co18 O16 88.30(8) . 2_655 ? N8 Co18 O16 82.65(9) 2_655 2_655 ? N8 Co18 O16 96.99(9) . 2_655 ? O1 Co18 O16 88.30(8) 2_655 . ? O1 Co18 O16 155.66(8) . . ? N8 Co18 O16 96.99(9) 2_655 . ? N8 Co18 O16 82.65(9) . . ? O16 Co18 O16 74.96(10) 2_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -179.7(3) . . . . ? C7 C2 C3 C4 1.5(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C5 C6 C7 C2 1.8(5) . . . . ? C5 C6 C7 N8 -179.4(3) . . . . ? O1 C2 C7 C6 178.7(3) . . . . ? C3 C2 C7 C6 -2.5(4) . . . . ? O1 C2 C7 N8 -0.2(4) . . . . ? C3 C2 C7 N8 178.6(3) . . . . ? N8 C9 C10 C15 14.6(5) . . . . ? N8 C9 C10 C11 -166.0(3) . . . . ? C15 C10 C11 C12 0.0(5) . . . . ? C9 C10 C11 C12 -179.5(3) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C13 C14 C15 O16 179.4(3) . . . . ? C13 C14 C15 C10 0.8(5) . . . . ? C11 C10 C15 C14 -0.7(5) . . . . ? C9 C10 C15 C14 178.7(3) . . . . ? C11 C10 C15 O16 -179.3(3) . . . . ? C9 C10 C15 O16 0.1(5) . . . . ? C10 C9 N8 C7 179.9(3) . . . . ? C10 C9 N8 Co18 16.6(4) . . . . ? C6 C7 N8 C9 19.4(5) . . . . ? C2 C7 N8 C9 -161.8(3) . . . . ? C6 C7 N8 Co18 -175.1(3) . . . . ? C2 C7 N8 Co18 3.8(3) . . . . ? C3 C2 O1 Co18 177.7(2) . . . . ? C7 C2 O1 Co18 -3.6(3) . . . . ? C14 C15 O16 C17 -85.2(3) . . . . ? C10 C15 O16 C17 93.4(3) . . . . ? C14 C15 O16 Co18 143.1(2) . . . . ? C10 C15 O16 Co18 -38.3(3) . . . . ? C17 C17 O16 C15 -178.2(3) 2_655 . . . ? C17 C17 O16 Co18 -43.5(3) 2_655 . . . ? C2 O1 Co18 O1 100.02(19) . . . 2_655 ? C2 O1 Co18 N8 -175.26(19) . . . 2_655 ? C2 O1 Co18 N8 4.35(19) . . . . ? C2 O1 Co18 O16 -92.95(19) . . . 2_655 ? C2 O1 Co18 O16 -47.0(3) . . . . ? C9 N8 Co18 O1 48.6(3) . . . 2_655 ? C7 N8 Co18 O1 -116.16(19) . . . 2_655 ? C9 N8 Co18 O1 160.3(3) . . . . ? C7 N8 Co18 O1 -4.41(19) . . . . ? C9 N8 Co18 N8 -75.5(2) . . . 2_655 ? C7 N8 Co18 N8 119.7(2) . . . 2_655 ? C9 N8 Co18 O16 -112.4(3) . . . 2_655 ? C7 N8 Co18 O16 82.87(19) . . . 2_655 ? C9 N8 Co18 O16 -38.6(3) . . . . ? C7 N8 Co18 O16 156.7(2) . . . . ? C15 O16 Co18 O1 -50.42(19) . . . 2_655 ? C17 O16 Co18 O1 177.88(18) . . . 2_655 ? C15 O16 Co18 O1 99.4(2) . . . . ? C17 O16 Co18 O1 -32.3(3) . . . . ? C15 O16 Co18 N8 -132.14(19) . . . 2_655 ? C17 O16 Co18 N8 96.16(19) . . . 2_655 ? C15 O16 Co18 N8 48.14(19) . . . . ? C17 O16 Co18 N8 -83.56(19) . . . . ? C15 O16 Co18 O16 147.4(2) . . . 2_655 ? C17 O16 Co18 O16 15.74(14) . . . 2_655 ? 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 O19 H19 O1 0.841(3) 1.768(13) 2.589(3) 165(5) 2_655 C3 H3 O19 0.95 2.65 3.291(4) 125.4 2_655 C17 H17B O19 0.99 2.61 3.458(4) 143.2 4_565 C14 H14 O22 0.95 2.54 3.397(5) 150.3 3_645 C17 H17A O22 0.99 2.65 3.410(5) 134.1 3_645 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.248 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.067 data_importtr _database_code_CSD 216933 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N Ni0.50 O4' _chemical_formula_weight 314.64 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(2)/n _symmetry_Int_Tables_number 86 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 13.925(2) _cell_length_b 13.925(2) _cell_length_c 14.181(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2749.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9384 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.682 _exptl_crystal_description Blocks _exptl_crystal_colour Orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas None _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Dx = 30 mm; 20 sec./deg.; 2 deg; 3 sets; 152 frames; Mos. 0.408(13) deg. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18110 _diffrn_reflns_av_R_equivalents 0.1233 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2594 _reflns_number_gt 1914 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0721P)^2^+12.2047P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2594 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.1863 _refine_ls_wR_factor_gt 0.1695 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C2 C 0.9040(4) 0.1620(4) 0.6484(4) 0.0284(12) Uani 1 1 d . . . C3 C 0.9645(4) 0.0972(4) 0.5997(4) 0.0318(12) Uani 1 1 d . . . H3 H 0.9368 0.0427 0.5699 0.038 Uiso 1 1 calc R . . C4 C 1.0617(4) 0.1105(4) 0.5943(4) 0.0377(14) Uani 1 1 d . . . H4 H 1.1003 0.0657 0.5609 0.045 Uiso 1 1 calc R . . C5 C 1.1039(4) 0.1895(4) 0.6376(4) 0.0377(14) Uani 1 1 d . . . H5 H 1.1715 0.1982 0.6344 0.045 Uiso 1 1 calc R . . C6 C 1.0484(4) 0.2549(4) 0.6848(4) 0.0341(13) Uani 1 1 d . . . H6 H 1.0777 0.3090 0.7139 0.041 Uiso 1 1 calc R . . C7 C 0.9491(4) 0.2426(4) 0.6905(3) 0.0262(11) Uani 1 1 d . . . C9 C 0.9060(4) 0.3926(4) 0.7556(4) 0.0288(12) Uani 1 1 d . . . H9 H 0.9681 0.4139 0.7374 0.035 Uiso 1 1 calc R . . C10 C 0.8433(4) 0.4619(4) 0.8022(4) 0.0301(12) Uani 1 1 d . . . C11 C 0.8724(4) 0.5581(4) 0.7988(4) 0.0331(13) Uani 1 1 d . . . H11 H 0.9300 0.5747 0.7668 0.040 Uiso 1 1 calc R . . C12 C 0.8188(4) 0.6285(4) 0.8411(4) 0.0389(14) Uani 1 1 d . . . H12 H 0.8391 0.6936 0.8374 0.047 Uiso 1 1 calc R . . C13 C 0.7362(5) 0.6059(4) 0.8886(4) 0.0384(14) Uani 1 1 d . . . H13 H 0.7003 0.6552 0.9187 0.046 Uiso 1 1 calc R . . C14 C 0.7046(4) 0.5116(4) 0.8931(4) 0.0333(13) Uani 1 1 d . . . H14 H 0.6467 0.4962 0.9251 0.040 Uiso 1 1 calc R . . C15 C 0.7581(4) 0.4401(4) 0.8505(3) 0.0270(11) Uani 1 1 d . . . C17 C 0.7648(4) 0.3016(4) 0.9451(3) 0.0282(11) Uani 1 1 d . . . H17A H 0.7388 0.3346 1.0014 0.034 Uiso 1 1 calc R . . H17B H 0.8357 0.3067 0.9464 0.034 Uiso 1 1 calc R . . C20 C 0.8371(5) 0.4835(5) 0.5144(6) 0.0503(17) Uani 1 1 d . . . N8 N 0.8837(3) 0.3058(3) 0.7374(3) 0.0281(10) Uani 1 1 d . . . O1 O 0.8094(3) 0.1512(3) 0.6544(3) 0.0316(9) Uani 1 1 d . . . O16 O 0.7268(3) 0.3458(2) 0.8590(2) 0.0268(8) Uani 1 1 d . . . O19 O 0.7482(4) 0.4856(4) 0.5450(4) 0.0692(15) Uani 1 1 d D . . H19 H 0.741(7) 0.446(6) 0.589(5) 0.104 Uiso 1 1 d D . . O21 O 0.8970(5) 0.4359(5) 0.5553(4) 0.093(2) Uani 1 1 d . . . C22 C 0.8554(8) 0.5398(7) 0.4312(7) 0.091(3) Uani 1 1 d . . . H22A H 0.9233 0.5582 0.4295 0.136 Uiso 1 1 calc R . . H22B H 0.8154 0.5977 0.4324 0.136 Uiso 1 1 calc R . . H22C H 0.8399 0.5019 0.3750 0.136 Uiso 1 1 calc R . . Ni18 Ni 0.7500 0.2500 0.73973(6) 0.0188(3) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.035(3) 0.026(3) 0.024(3) 0.000(2) -0.002(2) 0.005(2) C3 0.038(3) 0.030(3) 0.028(3) -0.003(2) -0.002(2) 0.004(2) C4 0.042(4) 0.034(3) 0.038(3) -0.008(2) -0.002(3) 0.005(3) C5 0.027(3) 0.049(4) 0.037(3) 0.001(3) -0.001(2) 0.000(3) C6 0.037(3) 0.033(3) 0.032(3) 0.001(2) -0.006(2) 0.000(3) C7 0.030(3) 0.024(3) 0.024(3) -0.002(2) -0.003(2) 0.007(2) C9 0.029(3) 0.030(3) 0.027(3) 0.002(2) -0.003(2) 0.000(2) C10 0.033(3) 0.030(3) 0.028(3) 0.003(2) -0.004(2) 0.006(2) C11 0.035(3) 0.031(3) 0.034(3) 0.006(2) -0.006(2) -0.003(2) C12 0.047(4) 0.025(3) 0.044(3) 0.003(3) -0.007(3) -0.005(3) C13 0.052(4) 0.025(3) 0.039(3) 0.000(2) 0.001(3) 0.004(3) C14 0.038(3) 0.029(3) 0.033(3) 0.003(2) 0.002(2) 0.009(2) C15 0.035(3) 0.020(3) 0.026(3) 0.004(2) 0.001(2) 0.002(2) C17 0.040(3) 0.027(3) 0.018(3) 0.001(2) -0.005(2) 0.002(2) C20 0.030(3) 0.049(4) 0.071(5) -0.015(4) -0.001(3) -0.008(3) N8 0.035(3) 0.029(2) 0.021(2) -0.0021(18) -0.0015(18) -0.0014(19) O1 0.029(2) 0.034(2) 0.032(2) -0.0104(16) 0.0000(16) -0.0021(16) O16 0.035(2) 0.0205(18) 0.0248(19) 0.0013(14) 0.0030(15) 0.0009(15) O19 0.062(3) 0.074(4) 0.071(4) 0.027(3) 0.008(3) 0.009(3) O21 0.101(5) 0.107(5) 0.070(4) 0.024(4) -0.007(4) 0.009(4) C22 0.106(8) 0.084(7) 0.082(7) 0.010(5) -0.011(6) 0.006(6) Ni18 0.0231(5) 0.0186(5) 0.0148(4) 0.000 0.000 -0.0004(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 C2 O1 1.329(6) . ? C2 C3 1.414(7) . ? C2 C7 1.418(7) . ? C3 C4 1.369(8) . ? C3 H3 0.9500 . ? C4 C5 1.391(8) . ? C4 H4 0.9500 . ? C5 C6 1.370(8) . ? C5 H5 0.9500 . ? C6 C7 1.396(8) . ? C6 H6 0.9500 . ? C7 N8 1.431(6) . ? C9 N8 1.274(7) . ? C9 C10 1.460(7) . ? C9 H9 0.9500 . ? C10 C11 1.401(8) . ? C10 C15 1.402(7) . ? C11 C12 1.371(8) . ? C11 H11 0.9500 . ? C12 C13 1.370(8) . ? C12 H12 0.9500 . ? C13 C14 1.387(8) . ? C13 H13 0.9500 . ? C14 C15 1.382(7) . ? C14 H14 0.9500 . ? C15 O16 1.389(6) . ? C17 O16 1.466(6) . ? C17 C17 1.495(10) 2_655 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C20 O21 1.214(9) . ? C20 O19 1.311(8) . ? C20 C22 1.439(12) . ? N8 Ni18 2.018(4) . ? O1 Ni18 2.010(4) . ? O16 Ni18 2.178(3) . ? O19 H19 0.841(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Ni18 O1 2.010(4) 2_655 ? Ni18 N8 2.018(5) 2_655 ? Ni18 O16 2.178(3) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C2 C3 123.4(5) . . ? O1 C2 C7 120.1(4) . . ? C3 C2 C7 116.5(5) . . ? C4 C3 C2 122.0(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.2(5) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.3(5) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 120.8(5) . . ? C6 C7 N8 125.5(5) . . ? C2 C7 N8 113.6(4) . . ? N8 C9 C10 124.9(5) . . ? N8 C9 H9 117.6 . . ? C10 C9 H9 117.6 . . ? C11 C10 C15 118.0(5) . . ? C11 C10 C9 116.3(5) . . ? C15 C10 C9 125.8(5) . . ? C12 C11 C10 120.7(5) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.4(6) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 O16 118.3(5) . . ? C14 C15 C10 120.9(5) . . ? O16 C15 C10 120.8(5) . . ? O16 C17 C17 107.7(3) . 2_655 ? O16 C17 H17A 110.2 . . ? C17 C17 H17A 110.2 2_655 . ? O16 C17 H17B 110.2 . . ? C17 C17 H17B 110.2 2_655 . ? H17A C17 H17B 108.5 . . ? O21 C20 O19 120.2(8) . . ? O21 C20 C22 124.6(7) . . ? O19 C20 C22 115.2(7) . . ? C9 N8 C7 121.5(5) . . ? C9 N8 Ni18 126.0(4) . . ? C7 N8 Ni18 111.0(3) . . ? C2 O1 Ni18 111.7(3) . . ? C15 O16 C17 110.8(4) . . ? C15 O16 Ni18 117.7(3) . . ? C17 O16 Ni18 109.6(3) . . ? C20 O19 H19 111(7) . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O1 Ni18 O1 106.0(2) . 2_655 ? O1 Ni18 N8 96.11(16) . 2_655 ? O1 Ni18 N8 82.78(16) 2_655 2_655 ? O1 Ni18 N8 82.78(16) . . ? O1 Ni18 N8 96.11(16) 2_655 . ? N8 Ni18 N8 178.2(2) 2_655 . ? O1 Ni18 O16 161.37(14) . . ? O1 Ni18 O16 89.29(14) 2_655 . ? N8 Ni18 O16 96.41(15) 2_655 . ? N8 Ni18 O16 85.02(15) . . ? O1 Ni18 O16 89.29(14) . 2_655 ? O1 Ni18 O16 161.37(14) 2_655 2_655 ? N8 Ni18 O16 85.02(15) 2_655 2_655 ? N8 Ni18 O16 96.41(15) . 2_655 ? O16 Ni18 O16 78.12(18) . 2_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 179.6(5) . . . . ? C7 C2 C3 C4 0.7(8) . . . . ? C2 C3 C4 C5 0.2(9) . . . . ? C3 C4 C5 C6 -0.8(9) . . . . ? C4 C5 C6 C7 0.4(9) . . . . ? C5 C6 C7 C2 0.6(8) . . . . ? C5 C6 C7 N8 -179.8(5) . . . . ? O1 C2 C7 C6 180.0(5) . . . . ? C3 C2 C7 C6 -1.1(7) . . . . ? O1 C2 C7 N8 0.3(7) . . . . ? C3 C2 C7 N8 179.2(4) . . . . ? N8 C9 C10 C11 -167.4(5) . . . . ? N8 C9 C10 C15 13.5(8) . . . . ? C15 C10 C11 C12 -0.3(8) . . . . ? C9 C10 C11 C12 -179.5(5) . . . . ? C10 C11 C12 C13 0.8(9) . . . . ? C11 C12 C13 C14 -1.2(9) . . . . ? C12 C13 C14 C15 1.1(9) . . . . ? C13 C14 C15 O16 177.7(5) . . . . ? C13 C14 C15 C10 -0.6(8) . . . . ? C11 C10 C15 C14 0.3(8) . . . . ? C9 C10 C15 C14 179.3(5) . . . . ? C11 C10 C15 O16 -178.0(5) . . . . ? C9 C10 C15 O16 1.0(8) . . . . ? C10 C9 N8 C7 179.3(5) . . . . ? C10 C9 N8 Ni18 15.1(7) . . . . ? C6 C7 N8 C9 20.3(8) . . . . ? C2 C7 N8 C9 -160.0(5) . . . . ? C6 C7 N8 Ni18 -173.3(4) . . . . ? C2 C7 N8 Ni18 6.4(5) . . . . ? C3 C2 O1 Ni18 174.3(4) . . . . ? C7 C2 O1 Ni18 -6.9(6) . . . . ? C14 C15 O16 C17 -87.6(6) . . . . ? C10 C15 O16 C17 90.8(5) . . . . ? C14 C15 O16 Ni18 145.1(4) . . . . ? C10 C15 O16 Ni18 -36.6(6) . . . . ? C17 C17 O16 C15 -175.3(5) 2_655 . . . ? C17 C17 O16 Ni18 -43.6(5) 2_655 . . . ? C2 O1 Ni18 O1 102.3(3) . . . 2_655 ? C2 O1 Ni18 N8 -173.5(3) . . . 2_655 ? C2 O1 Ni18 N8 8.0(3) . . . . ? C2 O1 Ni18 O16 -41.5(6) . . . . ? C2 O1 Ni18 O16 -88.5(3) . . . 2_655 ? C9 N8 Ni18 O1 157.9(5) . . . . ? C7 N8 Ni18 O1 -7.8(3) . . . . ? C9 N8 Ni18 O1 52.5(5) . . . 2_655 ? C7 N8 Ni18 O1 -113.1(3) . . . 2_655 ? C9 N8 Ni18 N8 105.1(4) . . . 2_655 ? C7 N8 Ni18 N8 -60.5(3) . . . 2_655 ? C9 N8 Ni18 O16 -36.2(4) . . . . ? C7 N8 Ni18 O16 158.1(3) . . . . ? C9 N8 Ni18 O16 -113.6(4) . . . 2_655 ? C7 N8 Ni18 O16 80.7(3) . . . 2_655 ? C15 O16 Ni18 O1 95.0(5) . . . . ? C17 O16 Ni18 O1 -32.9(6) . . . . ? C15 O16 Ni18 O1 -50.4(3) . . . 2_655 ? C17 O16 Ni18 O1 -178.3(3) . . . 2_655 ? C15 O16 Ni18 N8 -133.1(3) . . . 2_655 ? C17 O16 Ni18 N8 99.1(3) . . . 2_655 ? C15 O16 Ni18 N8 45.8(3) . . . . ? C17 O16 Ni18 N8 -82.1(3) . . . . ? C15 O16 Ni18 O16 143.4(4) . . . 2_655 ? C17 O16 Ni18 O16 15.5(2) . . . 2_655 ? 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 C17 H17A O1 0.99 2.68 3.192(6) 112.5 3_645 C17 H17B O19 0.99 2.63 3.456(8) 141.4 4_565 C3 H3 O19 0.95 2.63 3.272(8) 125.3 2_655 O19 H19 O1 0.841(3) 1.78(4) 2.586(6) 159(10) 2_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.803 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.112 data_importtr_b _database_code_CSD 216934 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O3 Zn0.50' _chemical_formula_weight 289.96 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(2)/n _symmetry_Int_Tables_number 86 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 13.925(2) _cell_length_b 13.925(2) _cell_length_c 14.181(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2749.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9053 _cell_measurement_theta_max 25.682 _cell_measurement_theta_min 2.91 _exptl_crystal_description Blocks _exptl_crystal_colour Orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.939 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Dx = 30 mm; 20 sec./deg.; 2 deg; 3 sets; 152 frames Mos. 0.364(12) deg. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17541 _diffrn_reflns_av_R_equivalents 0.1048 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.69 _reflns_number_total 2496 _reflns_number_gt 1712 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0218P)^2^+3.4869P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2496 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.7382(2) 0.4353(2) 0.8265(2) 0.0195(7) Uani 1 1 d . . . C3 C 0.7072(2) 0.5169(2) 0.8795(2) 0.0237(7) Uani 1 1 d . . . H3 H 0.6500 0.5127 0.9157 0.028 Uiso 1 1 calc R . . C4 C 0.7597(2) 0.6037(2) 0.8794(2) 0.0297(8) Uani 1 1 d . . . H4 H 0.7376 0.6561 0.9163 0.036 Uiso 1 1 calc R . . C5 C 0.8438(2) 0.6140(2) 0.8258(2) 0.0296(8) Uani 1 1 d . . . H5 H 0.8772 0.6735 0.8240 0.036 Uiso 1 1 calc R . . C6 C 0.8777(2) 0.5342(2) 0.7747(2) 0.0241(7) Uani 1 1 d . . . H6 H 0.9351 0.5398 0.7389 0.029 Uiso 1 1 calc R . . C7 C 0.8272(2) 0.4453(2) 0.77568(19) 0.0196(7) Uani 1 1 d . . . C9 C 0.9477(2) 0.3482(2) 0.6979(2) 0.0210(7) Uani 1 1 d . . . H9 H 0.9890 0.4024 0.7012 0.025 Uiso 1 1 calc R . . C10 C 0.9869(2) 0.2581(2) 0.6575(2) 0.0198(7) Uani 1 1 d . . . C11 C 1.0896(2) 0.2475(2) 0.6564(2) 0.0267(8) Uani 1 1 d . . . H11 H 1.1287 0.3002 0.6748 0.032 Uiso 1 1 calc R . . C12 C 1.1341(2) 0.1607(2) 0.6287(2) 0.0311(8) Uani 1 1 d . . . H12 H 1.2021 0.1553 0.6287 0.037 Uiso 1 1 calc R . . C13 C 1.0767(2) 0.0822(2) 0.6012(2) 0.0313(8) Uani 1 1 d . . . H13 H 1.1062 0.0229 0.5850 0.038 Uiso 1 1 calc R . . C14 C 0.9748(2) 0.0912(2) 0.5972(2) 0.0259(7) Uani 1 1 d . . . H14 H 0.9363 0.0388 0.5768 0.031 Uiso 1 1 calc R . . C15 C 0.9315(2) 0.1789(2) 0.6241(2) 0.0193(7) Uani 1 1 d . . . C17 C 0.8043(2) 0.2406(2) 0.52943(19) 0.0228(7) Uani 1 1 d . . . H17A H 0.8224 0.2030 0.4729 0.027 Uiso 1 1 calc R . . H17B H 0.8397 0.3022 0.5279 0.027 Uiso 1 1 calc R . . N8 N 0.85934(16) 0.35788(16) 0.72962(15) 0.0173(5) Uani 1 1 d . . . O1 O 0.68708(14) 0.35210(14) 0.82546(14) 0.0203(5) Uani 1 1 d . . . O16 O 0.82916(14) 0.18723(14) 0.61458(13) 0.0199(5) Uani 1 1 d . . . Zn18 Zn 0.7500 0.2500 0.74539(3) 0.01659(13) Uani 1 2 d S . . O19 O 0.8505(3) 0.50691(18) 0.3758(2) 0.0634(9) Uani 1 1 d D . . H19 H 0.846(4) 0.4482(9) 0.363(4) 0.095 Uiso 1 1 d D . . C20 C 0.8426(3) 0.5132(3) 0.4738(3) 0.0475(11) Uani 1 1 d . . . H20A H 0.8964 0.4793 0.5033 0.071 Uiso 1 1 calc R . . H20B H 0.7820 0.4839 0.4941 0.071 Uiso 1 1 calc R . . H20C H 0.8437 0.5808 0.4929 0.071 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 C2 0.0246(17) 0.0200(17) 0.0139(15) 0.0035(12) -0.0015(13) 0.0015(13) C3 0.0281(18) 0.0221(17) 0.0208(16) 0.0026(13) 0.0038(14) 0.0030(14) C4 0.038(2) 0.0194(17) 0.0316(19) -0.0024(15) 0.0029(16) 0.0051(15) C5 0.035(2) 0.0187(17) 0.0354(19) 0.0004(15) -0.0024(16) -0.0080(15) C6 0.0204(17) 0.0253(17) 0.0266(18) 0.0033(13) 0.0022(13) -0.0028(13) C7 0.0188(16) 0.0211(16) 0.0187(16) 0.0014(12) -0.0024(12) 0.0023(13) C9 0.0207(17) 0.0219(17) 0.0204(17) 0.0007(13) 0.0019(13) -0.0052(13) C10 0.0195(17) 0.0260(17) 0.0140(15) 0.0006(13) 0.0031(12) -0.0023(13) C11 0.0217(18) 0.037(2) 0.0209(17) -0.0075(15) 0.0009(14) -0.0040(15) C12 0.0214(18) 0.046(2) 0.0262(18) -0.0056(16) -0.0011(14) 0.0072(16) C13 0.033(2) 0.033(2) 0.0284(19) -0.0052(15) -0.0016(16) 0.0118(16) C14 0.032(2) 0.0243(18) 0.0208(16) -0.0035(14) -0.0007(14) 0.0002(14) C15 0.0185(16) 0.0256(18) 0.0140(14) 0.0020(13) 0.0025(12) -0.0003(13) C17 0.0205(16) 0.0362(19) 0.0118(14) 0.0017(13) -0.0008(12) -0.0023(15) N8 0.0180(13) 0.0195(13) 0.0144(13) 0.0015(10) 0.0012(10) -0.0009(10) O1 0.0216(11) 0.0212(11) 0.0181(11) -0.0020(9) 0.0040(9) -0.0037(9) O16 0.0187(11) 0.0263(12) 0.0148(10) 0.0012(9) 0.0008(9) -0.0018(9) Zn18 0.0177(3) 0.0187(3) 0.0133(2) 0.000 0.000 -0.0027(2) O19 0.114(3) 0.0274(15) 0.0484(19) -0.0056(14) -0.0186(18) -0.0014(17) C20 0.065(3) 0.030(2) 0.047(3) -0.0101(17) -0.019(2) 0.0060(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O1 1.360(3) . ? C2 C3 1.429(4) . ? C2 C7 1.441(4) . ? C3 C4 1.411(4) . ? C3 H3 0.9500 . ? C4 C5 1.404(4) . ? C4 H4 0.9500 . ? C5 C6 1.408(4) . ? C5 H5 0.9500 . ? C6 C7 1.423(4) . ? C6 H6 0.9500 . ? C7 N8 1.452(4) . ? C9 N8 1.317(4) . ? C9 C10 1.483(4) . ? C9 H9 0.9500 . ? C10 C15 1.427(4) . ? C10 C11 1.439(4) . ? C11 C12 1.414(4) . ? C11 H11 0.9500 . ? C12 C13 1.408(5) . ? C12 H12 0.9500 . ? C13 C14 1.426(5) . ? C13 H13 0.9500 . ? C14 C15 1.414(4) . ? C14 H14 0.9500 . ? C15 O16 1.436(3) . ? C17 O16 1.459(3) . ? C17 C17 1.535(6) 2_655 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? N8 Zn18 2.151(2) . ? O1 Zn18 2.0195(19) . ? O16 Zn18 2.328(2) . ? Zn18 O1 2.0195(19) 2_655 ? Zn18 N8 2.151(2) 2_655 ? Zn18 O16 2.328(2) 2_655 ? O19 C20 1.397(5) . ? O19 H19 0.840(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C2 C3 121.7(3) . . ? O1 C2 C7 121.8(3) . . ? C3 C2 C7 116.5(3) . . ? C4 C3 C2 121.6(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 121.4(3) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.5(3) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C7 121.1(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 120.9(3) . . ? C6 C7 N8 124.9(3) . . ? C2 C7 N8 114.1(2) . . ? N8 C9 C10 124.2(3) . . ? N8 C9 H9 117.9 . . ? C10 C9 H9 117.9 . . ? C15 C10 C11 117.0(3) . . ? C15 C10 C9 125.7(3) . . ? C11 C10 C9 117.2(3) . . ? C12 C11 C10 121.8(3) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C10 121.8(3) . . ? C14 C15 O16 117.9(3) . . ? C10 C15 O16 120.3(2) . . ? O16 C17 C17 108.72(19) . 2_655 ? O16 C17 H17A 109.9 . . ? C17 C17 H17A 109.9 2_655 . ? O16 C17 H17B 109.9 . . ? C17 C17 H17B 109.9 2_655 . ? H17A C17 H17B 108.3 . . ? C9 N8 C7 121.8(2) . . ? C9 N8 Zn18 128.7(2) . . ? C7 N8 Zn18 108.72(17) . . ? C2 O1 Zn18 112.28(17) . . ? C15 O16 C17 110.8(2) . . ? C15 O16 Zn18 115.18(16) . . ? C17 O16 Zn18 110.86(16) . . ? O1 Zn18 O1 111.57(11) 2_655 . ? O1 Zn18 N8 82.75(8) 2_655 2_655 ? O1 Zn18 N8 104.07(8) . 2_655 ? O1 Zn18 N8 104.07(8) 2_655 . ? O1 Zn18 N8 82.75(8) . . ? N8 Zn18 N8 168.06(12) 2_655 . ? O1 Zn18 O16 88.75(8) 2_655 . ? O1 Zn18 O16 156.60(7) . . ? N8 Zn18 O16 89.43(8) 2_655 . ? N8 Zn18 O16 81.04(8) . . ? O1 Zn18 O16 156.60(7) 2_655 2_655 ? O1 Zn18 O16 88.75(8) . 2_655 ? N8 Zn18 O16 81.04(8) 2_655 2_655 ? N8 Zn18 O16 89.43(8) . 2_655 ? O16 Zn18 O16 74.35(10) . 2_655 ? C20 O19 H19 106(4) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -179.1(3) . . . . ? C7 C2 C3 C4 2.1(4) . . . . ? C2 C3 C4 C5 1.1(5) . . . . ? C3 C4 C5 C6 -2.7(5) . . . . ? C4 C5 C6 C7 1.1(5) . . . . ? C5 C6 C7 C2 2.2(4) . . . . ? C5 C6 C7 N8 -176.4(3) . . . . ? O1 C2 C7 C6 177.5(3) . . . . ? C3 C2 C7 C6 -3.6(4) . . . . ? O1 C2 C7 N8 -3.8(4) . . . . ? C3 C2 C7 N8 175.0(2) . . . . ? N8 C9 C10 C15 17.5(5) . . . . ? N8 C9 C10 C11 -159.0(3) . . . . ? C15 C10 C11 C12 -3.5(4) . . . . ? C9 C10 C11 C12 173.2(3) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C14 2.6(5) . . . . ? C12 C13 C14 C15 -1.9(5) . . . . ? C13 C14 C15 C10 -1.7(4) . . . . ? C13 C14 C15 O16 176.8(3) . . . . ? C11 C10 C15 C14 4.3(4) . . . . ? C9 C10 C15 C14 -172.2(3) . . . . ? C11 C10 C15 O16 -174.1(3) . . . . ? C9 C10 C15 O16 9.4(4) . . . . ? C10 C9 N8 C7 174.8(3) . . . . ? C10 C9 N8 Zn18 5.9(4) . . . . ? C6 C7 N8 C9 13.5(4) . . . . ? C2 C7 N8 C9 -165.1(3) . . . . ? C6 C7 N8 Zn18 -175.6(2) . . . . ? C2 C7 N8 Zn18 5.7(3) . . . . ? C3 C2 O1 Zn18 -179.4(2) . . . . ? C7 C2 O1 Zn18 -0.6(3) . . . . ? C14 C15 O16 C17 -100.6(3) . . . . ? C10 C15 O16 C17 77.9(3) . . . . ? C14 C15 O16 Zn18 132.6(2) . . . . ? C10 C15 O16 Zn18 -48.9(3) . . . . ? C17 C17 O16 C15 -172.4(3) 2_655 . . . ? C17 C17 O16 Zn18 -43.2(3) 2_655 . . . ? C2 O1 Zn18 O1 105.34(18) . . . 2_655 ? C2 O1 Zn18 N8 -167.00(18) . . . 2_655 ? C2 O1 Zn18 N8 3.03(18) . . . . ? C2 O1 Zn18 O16 -43.4(3) . . . . ? C2 O1 Zn18 O16 -86.56(18) . . . 2_655 ? C9 N8 Zn18 O1 54.7(2) . . . 2_655 ? C7 N8 Zn18 O1 -115.32(17) . . . 2_655 ? C9 N8 Zn18 O1 165.2(2) . . . . ? C7 N8 Zn18 O1 -4.82(16) . . . . ? C9 N8 Zn18 N8 -69.1(2) . . . 2_655 ? C7 N8 Zn18 N8 120.86(16) . . . 2_655 ? C9 N8 Zn18 O16 -31.8(2) . . . . ? C7 N8 Zn18 O16 158.25(17) . . . . ? C9 N8 Zn18 O16 -106.0(2) . . . 2_655 ? C7 N8 Zn18 O16 84.00(17) . . . 2_655 ? C15 O16 Zn18 O1 -54.05(18) . . . 2_655 ? C17 O16 Zn18 O1 179.22(17) . . . 2_655 ? C15 O16 Zn18 O1 97.1(2) . . . . ? C17 O16 Zn18 O1 -29.6(3) . . . . ? C15 O16 Zn18 N8 -136.81(18) . . . 2_655 ? C17 O16 Zn18 N8 96.45(17) . . . 2_655 ? C15 O16 Zn18 N8 50.40(17) . . . . ? C17 O16 Zn18 N8 -76.33(17) . . . . ? C15 O16 Zn18 O16 142.3(2) . . . 2_655 ? C17 O16 Zn18 O16 15.60(14) . . . 2_655 ? 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 C17 H17A O1 0.99 2.62 3.134(3) 112.2 4_564 O19 H19 O1 0.840(3) 1.959(8) 2.794(3) 173(5) 4_564 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.318 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.061 data_importo _database_code_CSD 216935 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N O2' _chemical_formula_weight 226.25 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.2540(2) _cell_length_b 8.3950(4) _cell_length_c 15.9940(6) _cell_angle_alpha 90.000(1) _cell_angle_beta 90.000(1) _cell_angle_gamma 90.000(2) _cell_volume 2316.69(14) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5348 _cell_measurement_theta_max 22.465 _cell_measurement_theta_min 2.91 _exptl_crystal_description Prisms _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm; 200 sec./deg.; 2 deg.; 5 sets; 237 frames; mos. 0.66(3) deg. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9192 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 22.44 _reflns_number_total 1496 _reflns_number_gt 1104 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0662P)^2^+3.3758P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1496 _refine_ls_number_parameters 157 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1711 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C2 C 0.8545(3) 0.0385(5) 0.6230(3) 0.0720(14) Uani 1 1 d . . . C3 C 0.7940(3) -0.0377(5) 0.6669(4) 0.0780(16) Uani 1 1 d . . . H3 H 0.7660 -0.1219 0.6412 0.094 Uiso 1 1 calc R . . C4 C 0.7758(3) 0.0082(6) 0.7448(4) 0.0811(15) Uani 1 1 d . . . H4 H 0.7345 -0.0430 0.7734 0.097 Uiso 1 1 calc R . . C5 C 0.8150(2) 0.1250(5) 0.7828(3) 0.0681(13) Uani 1 1 d . . . H5 H 0.8022 0.1543 0.8384 0.082 Uiso 1 1 calc R . . C6 C 0.8740(2) 0.2033(4) 0.7414(3) 0.0567(11) Uani 1 1 d . . . H6 H 0.9009 0.2864 0.7694 0.068 Uiso 1 1 calc R . . C7 C 0.8951(2) 0.1646(4) 0.6609(3) 0.0505(11) Uani 1 1 d . . . C9 C 0.9744(2) 0.3805(5) 0.6286(2) 0.0489(10) Uani 1 1 d . . . H9 H 0.9405 0.4413 0.6628 0.059 Uiso 1 1 calc R . . C10 C 1.0424(2) 0.4591(5) 0.5939(2) 0.0471(10) Uani 1 1 d . . . C11 C 1.0939(2) 0.3804(5) 0.5412(2) 0.0607(12) Uani 1 1 d . . . H11 H 1.0834 0.2737 0.5251 0.073 Uiso 1 1 calc R . . C12 C 1.1598(3) 0.4544(6) 0.5119(3) 0.0713(14) Uani 1 1 d . . . H12 H 1.1940 0.3995 0.4753 0.086 Uiso 1 1 calc R . . C13 C 1.1761(3) 0.6085(6) 0.5361(3) 0.0667(13) Uani 1 1 d . . . H13 H 1.2222 0.6585 0.5170 0.080 Uiso 1 1 calc R . . C14 C 1.1262(2) 0.6911(5) 0.5878(2) 0.0570(11) Uani 1 1 d . . . H14 H 1.1376 0.7974 0.6040 0.068 Uiso 1 1 calc R . . C15 C 1.0592(2) 0.6172(5) 0.6158(2) 0.0479(10) Uani 1 1 d . . . C17 C 1.0268(2) 0.8268(4) 0.7133(2) 0.0499(10) Uani 1 1 d . . . H17A H 1.0210 0.9261 0.6805 0.060 Uiso 1 1 calc R . . H17B H 1.0814 0.8177 0.7320 0.060 Uiso 1 1 calc R . . N8 N 0.95773(19) 0.2341(4) 0.61554(19) 0.0521(9) Uani 1 1 d . . . O1 O 0.8755(3) -0.0017(4) 0.5441(2) 0.1084(14) Uani 1 1 d D . . H1 H 0.9222(14) 0.011(10) 0.530(5) 0.163 Uiso 1 1 d D . . O16 O 1.00509(15) 0.6913(3) 0.66439(17) 0.0581(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 C2 0.105(4) 0.052(3) 0.059(3) -0.001(2) -0.041(3) 0.007(3) C3 0.093(4) 0.039(3) 0.102(4) 0.019(3) -0.054(3) -0.035(3) C4 0.075(4) 0.069(3) 0.099(4) 0.012(3) -0.031(3) -0.006(3) C5 0.051(3) 0.045(2) 0.109(4) -0.003(3) 0.000(3) -0.004(2) C6 0.042(2) 0.041(2) 0.087(3) -0.017(2) -0.001(2) -0.003(2) C7 0.052(3) 0.030(2) 0.070(3) -0.004(2) -0.028(2) 0.0023(19) C9 0.047(2) 0.050(3) 0.050(2) -0.004(2) -0.0089(19) 0.012(2) C10 0.047(2) 0.051(3) 0.044(2) -0.0014(19) -0.0055(19) 0.011(2) C11 0.068(3) 0.060(3) 0.054(2) 0.007(2) 0.002(2) 0.020(3) C12 0.072(3) 0.081(4) 0.062(3) 0.010(3) 0.017(2) 0.025(3) C13 0.058(3) 0.087(4) 0.056(3) 0.018(3) 0.007(2) 0.005(3) C14 0.056(3) 0.065(3) 0.050(2) 0.008(2) -0.006(2) -0.003(2) C15 0.041(2) 0.061(3) 0.042(2) 0.001(2) -0.0068(18) 0.008(2) C17 0.054(2) 0.041(2) 0.056(2) -0.0001(18) -0.0083(18) -0.0044(18) N8 0.059(2) 0.045(2) 0.0527(19) -0.0093(16) -0.0163(17) 0.0119(17) O1 0.201(4) 0.055(2) 0.069(2) -0.0113(18) -0.033(3) -0.009(3) O16 0.0446(16) 0.0587(17) 0.0711(18) -0.0246(15) -0.0012(14) -0.0077(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 O1 1.356(6) . ? C2 C7 1.406(5) . ? C2 C3 1.412(7) . ? C3 C4 1.341(7) . ? C3 H3 0.9500 . ? C4 C5 1.337(6) . ? C4 H4 0.9500 . ? C5 C6 1.381(6) . ? C5 H5 0.9500 . ? C6 C7 1.377(6) . ? C6 H6 0.9500 . ? C7 N8 1.427(5) . ? C9 N8 1.279(5) . ? C9 C10 1.456(5) . ? C9 H9 0.9500 . ? C10 C11 1.392(5) . ? C10 C15 1.403(5) . ? C11 C12 1.378(6) . ? C11 H11 0.9500 . ? C12 C13 1.379(6) . ? C12 H12 0.9500 . ? C13 C14 1.381(6) . ? C13 H13 0.9500 . ? C14 C15 1.386(5) . ? C14 H14 0.9500 . ? C15 O16 1.364(4) . ? C17 O16 1.431(4) . ? C17 C17 1.494(7) 4_756 ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O1 H1 0.841(3) . ? 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 C2 C7 117.1(5) . . ? O1 C2 C3 123.2(4) . . ? C7 C2 C3 119.7(4) . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.9(5) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.3(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 122.0(4) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C6 C7 C2 116.7(4) . . ? C6 C7 N8 125.4(3) . . ? C2 C7 N8 117.7(4) . . ? N8 C9 C10 123.6(4) . . ? N8 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C11 C10 C15 117.9(4) . . ? C11 C10 C9 122.0(4) . . ? C15 C10 C9 120.0(3) . . ? C12 C11 C10 121.3(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.7(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.8(4) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C15 119.3(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? O16 C15 C14 123.4(4) . . ? O16 C15 C10 115.6(3) . . ? C14 C15 C10 121.0(4) . . ? O16 C17 C17 105.5(3) . 4_756 ? O16 C17 H17A 110.6 . . ? C17 C17 H17A 110.6 4_756 . ? O16 C17 H17B 110.6 . . ? C17 C17 H17B 110.6 4_756 . ? H17A C17 H17B 108.8 . . ? C9 N8 C7 118.7(3) . . ? C2 O1 H1 118(6) . . ? C15 O16 C17 119.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -179.7(4) . . . . ? C7 C2 C3 C4 -0.9(7) . . . . ? C2 C3 C4 C5 -0.9(7) . . . . ? C3 C4 C5 C6 1.5(7) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C5 C6 C7 C2 -1.3(6) . . . . ? C5 C6 C7 N8 -176.7(4) . . . . ? O1 C2 C7 C6 -179.2(4) . . . . ? C3 C2 C7 C6 1.9(6) . . . . ? O1 C2 C7 N8 -3.5(5) . . . . ? C3 C2 C7 N8 177.7(4) . . . . ? N8 C9 C10 C11 1.9(6) . . . . ? N8 C9 C10 C15 -175.7(3) . . . . ? C15 C10 C11 C12 0.6(5) . . . . ? C9 C10 C11 C12 -177.0(4) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C11 C12 C13 C14 -1.5(6) . . . . ? C12 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 O16 -177.4(3) . . . . ? C13 C14 C15 C10 1.4(5) . . . . ? C11 C10 C15 O16 177.1(3) . . . . ? C9 C10 C15 O16 -5.2(5) . . . . ? C11 C10 C15 C14 -1.8(5) . . . . ? C9 C10 C15 C14 175.9(3) . . . . ? C10 C9 N8 C7 172.3(3) . . . . ? C6 C7 N8 C9 -33.3(5) . . . . ? C2 C7 N8 C9 151.4(3) . . . . ? C14 C15 O16 C17 -22.6(5) . . . . ? C10 C15 O16 C17 158.5(3) . . . . ? C17 C17 O16 C15 -151.9(3) 4_756 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.44 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.499 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.045