# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_publication_text _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Seth M. Cohen' _publ_contact_author_address ;U.C. San Diego Department of Chemistry and Biochemistry 9500 Gilman Drive La Jolla, CA 92093-0358 ; _publ_contact_author_email scohen@ucsd.edu _publ_contact_author_phone 858-822-5596 _publ_contact_author_fax 858-822-5598 loop_ _publ_author_name _publ_author_address B.L.Tran ;U.C. San Diego Department of Chemistry and Biochemistry 9500 Gilman Drive La Jolla, CA 92093-0358 USA ; 'Seth M. Cohen' ;U.C. San Diego Department of Chemistry and Biochemistry 9500 Gilman Drive La Jolla, CA 92093-0358 USA ; data_3-OHFT _database_code_depnum_ccdc_archive 'CCDC 252675' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 O2 S' _chemical_formula_weight 254.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 22.269(4) _cell_length_b 3.8534(7) _cell_length_c 26.754(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2295.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1303 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 20.56 _exptl_crystal_description Plate _exptl_crystal_colour Orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type semi-emperical _exptl_absorpt_correction_T_min 0.661056 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12686 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_sigmaI/netI 0.1931 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.56 _reflns_number_total 5042 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.17(9) _refine_ls_number_reflns 5042 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 0.745 _refine_ls_restrained_S_all 0.745 _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 C20 C 1.1805(2) 0.2636(11) 0.14907(14) 0.0254(12) Uani 1 1 d . . . H20 H 1.2182 0.1535 0.1537 0.031 Uiso 1 1 calc R . . S1 S 0.21925(6) 0.4689(3) 0.47180(4) 0.0332(3) Uani 1 1 d . . . S2 S 1.07336(6) 0.6079(3) 0.28524(4) 0.0288(3) Uani 1 1 d . . . O2 O 0.37478(12) 0.5643(7) 0.36700(9) 0.0202(7) Uani 1 1 d . . . O4 O 1.01541(13) 0.7241(7) 0.12626(9) 0.0215(7) Uani 1 1 d . . . O3 O 0.96165(12) 0.9021(8) 0.25077(9) 0.0257(8) Uani 1 1 d . . . H3 H 0.9814 0.9097 0.2775 0.039 Uiso 1 1 calc R . . C3 C 0.27314(19) 0.3691(10) 0.37951(14) 0.0186(10) Uani 1 1 d . . . O1 O 0.33351(15) 0.7754(9) 0.49333(10) 0.0308(8) Uani 1 1 d . . . H1 H 0.2988 0.7946 0.5054 0.046 Uiso 1 1 calc R . . C2 C 0.2759(2) 0.4995(11) 0.43078(14) 0.0242(11) Uani 1 1 d . . . C25 C 0.92235(19) 0.9800(11) 0.14568(14) 0.0185(10) Uani 1 1 d . . . C15 C 0.4512(2) 1.0071(11) 0.47053(17) 0.0253(11) Uani 1 1 d . . . H15 H 0.4206 1.0401 0.4948 0.030 Uiso 1 1 calc R . . C7 C 0.3255(2) 0.2968(11) 0.30032(15) 0.0239(11) Uani 1 1 d . . . H7 H 0.3605 0.3261 0.2805 0.029 Uiso 1 1 calc R . . C8 C 0.3231(2) 0.4125(11) 0.35031(14) 0.0180(10) Uani 1 1 d . . . C11 C 0.4848(2) 0.7940(11) 0.39075(15) 0.0243(11) Uani 1 1 d . . . H11 H 0.4767 0.6803 0.3600 0.029 Uiso 1 1 calc R . . C24 C 0.9782(2) 0.8386(10) 0.16401(14) 0.0188(10) Uani 1 1 d . . . C14 C 0.5090(2) 1.1286(11) 0.47942(16) 0.0289(12) Uani 1 1 d . . . H14 H 0.5171 1.2466 0.5099 0.035 Uiso 1 1 calc R . . C23 C 1.0692(2) 0.5747(10) 0.13514(14) 0.0182(9) Uani 1 1 d . . . C30 C 0.88122(19) 1.1519(10) 0.17572(15) 0.0204(10) Uani 1 1 d . . . H30 H 0.8900 1.1837 0.2102 0.024 Uiso 1 1 calc R . . C19 C 1.14807(19) 0.3716(10) 0.18929(15) 0.0216(11) Uani 1 1 d . . . H19 H 1.1642 0.3415 0.2219 0.026 Uiso 1 1 calc R . . C18 C 1.09143(19) 0.5264(10) 0.18386(14) 0.0172(10) Uani 1 1 d . . . C6 C 0.2746(2) 0.1391(11) 0.28157(16) 0.0283(11) Uani 1 1 d . . . H6 H 0.2746 0.0598 0.2479 0.034 Uiso 1 1 calc R . . C9 C 0.3783(2) 0.6906(11) 0.41530(14) 0.0194(11) Uani 1 1 d . . . C5 C 0.2230(2) 0.0927(11) 0.31064(15) 0.0266(11) Uani 1 1 d . . . H5 H 0.1885 -0.0170 0.2969 0.032 Uiso 1 1 calc R . . C4 C 0.2227(2) 0.2071(11) 0.35915(15) 0.0230(11) Uani 1 1 d . . . H4 H 0.1878 0.1758 0.3791 0.028 Uiso 1 1 calc R . . C21 C 1.1578(2) 0.3156(11) 0.10036(15) 0.0234(11) Uani 1 1 d . . . H21 H 1.1807 0.2464 0.0721 0.028 Uiso 1 1 calc R . . C10 C 0.4382(2) 0.8335(11) 0.42498(14) 0.0209(11) Uani 1 1 d . . . C22 C 1.1019(2) 0.4681(11) 0.09386(15) 0.0225(11) Uani 1 1 d . . . H22 H 1.0861 0.4992 0.0612 0.027 Uiso 1 1 calc R . . C28 C 0.8141(2) 1.2395(11) 0.10635(16) 0.0250(11) Uani 1 1 d . . . H28 H 0.7778 1.3292 0.0929 0.030 Uiso 1 1 calc R . . C16 C 0.9980(2) 0.7948(10) 0.21277(14) 0.0198(10) Uani 1 1 d . . . C26 C 0.9076(2) 0.9425(12) 0.09446(15) 0.0246(11) Uani 1 1 d . . . H26 H 0.9349 0.8293 0.0725 0.029 Uiso 1 1 calc R . . C1 C 0.3297(2) 0.6538(11) 0.44533(14) 0.0221(11) Uani 1 1 d . . . C12 C 0.5424(2) 0.9142(12) 0.39988(15) 0.0307(12) Uani 1 1 d . . . H12 H 0.5728 0.8819 0.3754 0.037 Uiso 1 1 calc R . . C13 C 0.5562(2) 1.0828(11) 0.44479(16) 0.0328(13) Uani 1 1 d . . . H13 H 0.5957 1.1631 0.4517 0.039 Uiso 1 1 calc R . . C29 C 0.8281(2) 1.2774(11) 0.15702(15) 0.0247(12) Uani 1 1 d . . . H29 H 0.8006 1.3910 0.1787 0.030 Uiso 1 1 calc R . . C27 C 0.8550(2) 1.0667(11) 0.07656(16) 0.0249(11) Uani 1 1 d . . . H27 H 0.8459 1.0338 0.0422 0.030 Uiso 1 1 calc R . . C17 C 1.0542(2) 0.6445(11) 0.22476(14) 0.0216(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C20 0.031(3) 0.014(2) 0.031(3) 0.000(2) 0.004(2) 0.002(2) S1 0.0426(8) 0.0320(7) 0.0252(6) 0.0000(6) 0.0097(7) 0.0027(7) S2 0.0376(8) 0.0326(7) 0.0162(5) 0.0023(5) -0.0011(6) -0.0005(6) O2 0.029(2) 0.0203(17) 0.0112(14) -0.0001(13) -0.0025(13) 0.0030(15) O4 0.032(2) 0.0182(17) 0.0140(14) -0.0014(12) 0.0004(14) 0.0004(15) O3 0.030(2) 0.0336(19) 0.0135(15) 0.0000(14) 0.0058(14) 0.0018(17) C3 0.021(3) 0.016(2) 0.019(2) 0.0047(18) 0.000(2) 0.007(2) O1 0.050(2) 0.0302(19) 0.0124(15) -0.0040(14) 0.0025(15) 0.0021(18) C2 0.031(3) 0.019(3) 0.022(2) 0.006(2) 0.002(2) 0.003(2) C25 0.016(3) 0.017(2) 0.023(2) 0.0043(18) 0.000(2) -0.002(2) C15 0.043(3) 0.015(2) 0.017(2) 0.0044(19) -0.005(3) -0.001(2) C7 0.033(3) 0.019(3) 0.019(2) 0.0018(19) -0.003(2) 0.006(2) C8 0.023(3) 0.013(2) 0.018(2) 0.0002(18) -0.003(2) 0.001(2) C11 0.030(3) 0.023(3) 0.020(2) 0.0000(19) -0.004(2) -0.002(2) C24 0.023(3) 0.014(2) 0.020(2) -0.0001(18) 0.008(2) -0.008(2) C14 0.050(4) 0.015(2) 0.022(3) 0.003(2) -0.010(2) -0.002(2) C23 0.016(3) 0.016(2) 0.023(2) 0.0014(18) -0.002(2) 0.001(2) C30 0.029(3) 0.012(2) 0.020(2) 0.0050(19) -0.002(2) -0.001(2) C19 0.030(3) 0.013(2) 0.022(2) 0.0033(19) -0.006(2) -0.004(2) C18 0.023(3) 0.009(2) 0.019(2) 0.0016(17) 0.001(2) -0.003(2) C6 0.049(3) 0.015(2) 0.021(2) 0.000(2) -0.016(3) 0.002(2) C9 0.034(3) 0.011(2) 0.013(2) 0.0029(17) -0.005(2) 0.005(2) C5 0.034(3) 0.017(3) 0.028(3) 0.0032(19) -0.003(2) 0.000(2) C4 0.026(3) 0.018(2) 0.025(2) 0.0090(19) 0.003(2) 0.003(2) C21 0.025(3) 0.018(3) 0.027(3) -0.005(2) 0.012(2) -0.002(2) C10 0.033(3) 0.015(2) 0.015(2) 0.0032(18) -0.003(2) 0.008(2) C22 0.027(3) 0.021(3) 0.020(2) 0.0005(18) 0.003(2) -0.005(2) C28 0.027(3) 0.020(3) 0.028(3) 0.0091(19) 0.000(2) 0.000(2) C16 0.024(3) 0.018(2) 0.017(2) 0.0008(18) 0.004(2) 0.000(2) C26 0.030(3) 0.022(3) 0.022(2) -0.0007(19) -0.001(2) 0.002(2) C1 0.035(3) 0.018(2) 0.014(2) 0.0045(19) -0.002(2) 0.006(2) C12 0.039(3) 0.023(3) 0.029(3) 0.008(2) -0.005(2) 0.001(3) C13 0.041(4) 0.021(3) 0.037(3) 0.006(2) -0.012(3) -0.007(2) C29 0.035(3) 0.015(3) 0.024(3) 0.0014(18) 0.008(2) -0.001(2) C27 0.029(3) 0.022(3) 0.024(2) 0.001(2) -0.001(2) -0.005(2) C17 0.027(3) 0.015(2) 0.023(2) 0.0041(18) -0.005(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C20 C19 1.361(5) . ? C20 C21 1.412(5) . ? S1 C2 1.676(4) . ? S2 C17 1.679(4) . ? O2 C8 1.365(5) . ? O2 C9 1.383(4) . ? O4 C23 1.351(5) . ? O4 C24 1.379(4) . ? O3 C16 1.364(4) . ? C3 C8 1.371(5) . ? C3 C4 1.396(5) . ? C3 C2 1.462(5) . ? O1 C1 1.369(4) . ? C2 C1 1.394(6) . ? C25 C30 1.387(5) . ? C25 C26 1.416(5) . ? C25 C24 1.444(6) . ? C15 C14 1.391(6) . ? C15 C10 1.420(6) . ? C7 C6 1.380(6) . ? C7 C8 1.411(5) . ? C11 C12 1.386(6) . ? C11 C10 1.392(5) . ? C24 C16 1.387(5) . ? C14 C13 1.412(6) . ? C23 C22 1.385(5) . ? C23 C18 1.406(5) . ? C30 C29 1.372(6) . ? C19 C18 1.403(5) . ? C18 C17 1.446(5) . ? C6 C5 1.399(6) . ? C9 C1 1.355(5) . ? C9 C10 1.466(6) . ? C5 C4 1.371(5) . ? C21 C22 1.387(6) . ? C28 C27 1.382(6) . ? C28 C29 1.399(5) . ? C16 C17 1.416(5) . ? C26 C27 1.353(6) . ? C12 C13 1.400(6) . ? 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 C19 C20 C21 119.8(4) . . ? C8 O2 C9 120.3(3) . . ? C23 O4 C24 122.7(3) . . ? C8 C3 C4 119.1(4) . . ? C8 C3 C2 117.3(4) . . ? C4 C3 C2 123.6(4) . . ? C1 C2 C3 116.4(4) . . ? C1 C2 S1 119.6(3) . . ? C3 C2 S1 124.0(4) . . ? C30 C25 C26 117.2(4) . . ? C30 C25 C24 123.5(4) . . ? C26 C25 C24 119.3(4) . . ? C14 C15 C10 119.6(4) . . ? C6 C7 C8 117.0(4) . . ? O2 C8 C3 123.4(3) . . ? O2 C8 C7 114.5(4) . . ? C3 C8 C7 122.1(4) . . ? C12 C11 C10 122.5(4) . . ? O4 C24 C16 117.3(4) . . ? O4 C24 C25 112.9(3) . . ? C16 C24 C25 129.7(4) . . ? C15 C14 C13 122.3(4) . . ? O4 C23 C22 116.9(4) . . ? O4 C23 C18 122.1(4) . . ? C22 C23 C18 121.0(4) . . ? C29 C30 C25 121.7(4) . . ? C20 C19 C18 121.7(4) . . ? C19 C18 C23 117.9(4) . . ? C19 C18 C17 124.8(4) . . ? C23 C18 C17 117.3(4) . . ? C7 C6 C5 121.9(4) . . ? C1 C9 O2 118.2(4) . . ? C1 C9 C10 131.4(4) . . ? O2 C9 C10 110.4(4) . . ? C4 C5 C6 119.3(4) . . ? C5 C4 C3 120.6(4) . . ? C22 C21 C20 119.8(4) . . ? C11 C10 C15 117.7(4) . . ? C11 C10 C9 121.4(4) . . ? C15 C10 C9 120.9(4) . . ? C23 C22 C21 119.8(4) . . ? C27 C28 C29 117.5(4) . . ? O3 C16 C24 118.4(4) . . ? O3 C16 C17 118.7(4) . . ? C24 C16 C17 123.0(4) . . ? C27 C26 C25 120.4(4) . . ? C9 C1 O1 118.1(4) . . ? C9 C1 C2 124.5(4) . . ? O1 C1 C2 117.4(4) . . ? C11 C12 C13 120.6(4) . . ? C12 C13 C14 117.2(4) . . ? C30 C29 C28 120.6(4) . . ? C26 C27 C28 122.5(4) . . ? C16 C17 C18 117.6(3) . . ? C16 C17 S2 118.5(3) . . ? C18 C17 S2 123.9(3) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.310 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.060 #===END data_[Cu(3-OHFT)2] _database_code_depnum_ccdc_archive 'CCDC 252676' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H18 Cu O4 S2' _chemical_formula_weight 570.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.6476(17) _cell_length_b 9.8509(12) _cell_length_c 17.256(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.0970(10) _cell_angle_gamma 90.00 _cell_volume 2318.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7065 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.53 _exptl_crystal_description plate _exptl_crystal_colour dark _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 1.161 _exptl_absorpt_correction_type semi-emperical _exptl_absorpt_correction_T_min 0.781492 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19603 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5229 _reflns_number_gt 3930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.8080P] 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 5229 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Cu1 Cu 0.39167(2) 0.38866(3) 0.034913(16) 0.02085(10) Uani 1 1 d . . . S1 S 0.23435(4) 0.46306(7) 0.01218(3) 0.02308(15) Uani 1 1 d . . . S2 S 0.54569(5) 0.31380(7) 0.06357(4) 0.02586(16) Uani 1 1 d . . . O1 O 0.39585(12) 0.50322(17) 0.12446(9) 0.0235(4) Uani 1 1 d . . . O2 O 0.24498(12) 0.75448(16) 0.21108(9) 0.0213(4) Uani 1 1 d . . . O4 O 0.54468(12) 0.01623(16) -0.13185(9) 0.0217(4) Uani 1 1 d . . . O3 O 0.38820(12) 0.26807(17) -0.05154(9) 0.0235(4) Uani 1 1 d . . . C1 C 0.32144(17) 0.5821(2) 0.13610(13) 0.0189(5) Uani 1 1 d . . . C17 C 0.54843(18) 0.2005(2) -0.01003(13) 0.0210(5) Uani 1 1 d . . . C2 C 0.23494(17) 0.5739(2) 0.08701(13) 0.0186(5) Uani 1 1 d . . . C8 C 0.16160(17) 0.7486(2) 0.16592(13) 0.0207(5) Uani 1 1 d . . . C3 C 0.15398(17) 0.6608(2) 0.10272(13) 0.0190(5) Uani 1 1 d . . . C23 C 0.62658(18) 0.0249(2) -0.08480(14) 0.0220(5) Uani 1 1 d . . . C9 C 0.32419(17) 0.6768(2) 0.19678(13) 0.0188(5) Uani 1 1 d . . . C22 C 0.7039(2) -0.0600(3) -0.10289(15) 0.0267(6) Uani 1 1 d . . . H22 H 0.6984 -0.1206 -0.1456 0.032 Uiso 1 1 calc R . . C10 C 0.40545(17) 0.7050(2) 0.25158(13) 0.0183(5) Uani 1 1 d . . . C6 C 0.00162(18) 0.8369(3) 0.13979(15) 0.0253(6) Uani 1 1 d . . . H6 H -0.0502 0.8970 0.1516 0.030 Uiso 1 1 calc R . . C7 C 0.08584(18) 0.8357(3) 0.18584(15) 0.0248(5) Uani 1 1 d . . . H7 H 0.0924 0.8927 0.2301 0.030 Uiso 1 1 calc R . . C24 C 0.46474(18) 0.0950(2) -0.12170(13) 0.0206(5) Uani 1 1 d . . . C25 C 0.38810(18) 0.0676(2) -0.18083(13) 0.0208(5) Uani 1 1 d . . . C21 C 0.7886(2) -0.0538(3) -0.05733(15) 0.0296(6) Uani 1 1 d . . . H21 H 0.8426 -0.1101 -0.0691 0.035 Uiso 1 1 calc R . . C4 C 0.06509(18) 0.6638(3) 0.05772(13) 0.0218(5) Uani 1 1 d . . . H4 H 0.0566 0.6047 0.0145 0.026 Uiso 1 1 calc R . . C20 C 0.7961(2) 0.0346(3) 0.00631(15) 0.0278(6) Uani 1 1 d . . . H20 H 0.8547 0.0368 0.0377 0.033 Uiso 1 1 calc R . . C13 C 0.55667(18) 0.7628(2) 0.36011(14) 0.0223(5) Uani 1 1 d . . . H13 H 0.6079 0.7820 0.3973 0.027 Uiso 1 1 calc R . . C18 C 0.63171(18) 0.1156(2) -0.02274(14) 0.0203(5) Uani 1 1 d . . . C16 C 0.46403(18) 0.1903(2) -0.06146(13) 0.0204(5) Uani 1 1 d . . . C19 C 0.71919(19) 0.1181(3) 0.02348(15) 0.0249(6) Uani 1 1 d . . . H19 H 0.7249 0.1778 0.0667 0.030 Uiso 1 1 calc R . . C5 C -0.00858(18) 0.7509(3) 0.07582(14) 0.0242(5) Uani 1 1 d . . . H5 H -0.0673 0.7528 0.0445 0.029 Uiso 1 1 calc R . . C26 C 0.40458(19) -0.0301(2) -0.23856(14) 0.0235(5) Uani 1 1 d . . . H26 H 0.4629 -0.0828 -0.2362 0.028 Uiso 1 1 calc R . . C14 C 0.57242(18) 0.6741(2) 0.29991(14) 0.0218(5) Uani 1 1 d . . . H14 H 0.6348 0.6328 0.2954 0.026 Uiso 1 1 calc R . . C28 C 0.25004(19) 0.0238(3) -0.30263(14) 0.0242(5) Uani 1 1 d . . . H28 H 0.2036 0.0097 -0.3442 0.029 Uiso 1 1 calc R . . C15 C 0.49745(18) 0.6450(2) 0.24580(14) 0.0211(5) Uani 1 1 d . . . H15 H 0.5090 0.5839 0.2045 0.025 Uiso 1 1 calc R . . C12 C 0.46632(18) 0.8232(3) 0.36595(14) 0.0238(5) Uani 1 1 d . . . H12 H 0.4555 0.8842 0.4074 0.029 Uiso 1 1 calc R . . C30 C 0.29978(18) 0.1400(3) -0.18502(14) 0.0237(5) Uani 1 1 d . . . H30 H 0.2862 0.2048 -0.1460 0.028 Uiso 1 1 calc R . . C11 C 0.39140(18) 0.7964(2) 0.31247(14) 0.0226(5) Uani 1 1 d . . . H11 H 0.3298 0.8401 0.3169 0.027 Uiso 1 1 calc R . . C29 C 0.23210(19) 0.1183(3) -0.24532(15) 0.0252(6) Uani 1 1 d . . . H29 H 0.1727 0.1686 -0.2475 0.030 Uiso 1 1 calc R . . C27 C 0.33629(19) -0.0496(3) -0.29840(14) 0.0248(6) Uani 1 1 d . . . H27 H 0.3488 -0.1148 -0.3374 0.030 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 Cu1 0.02028(17) 0.02431(17) 0.01794(17) -0.00584(12) 0.00015(12) 0.00091(13) S1 0.0213(3) 0.0300(4) 0.0178(3) -0.0061(2) -0.0007(2) -0.0006(3) S2 0.0239(3) 0.0296(4) 0.0239(3) -0.0082(3) -0.0029(3) 0.0018(3) O1 0.0218(9) 0.0274(9) 0.0211(9) -0.0077(7) -0.0034(7) 0.0042(8) O2 0.0199(9) 0.0231(9) 0.0206(9) -0.0049(7) -0.0020(7) 0.0026(7) O4 0.0229(9) 0.0216(9) 0.0205(9) -0.0021(7) 0.0002(7) 0.0038(7) O3 0.0199(9) 0.0277(10) 0.0228(9) -0.0078(7) -0.0012(7) 0.0028(8) C1 0.0200(12) 0.0203(12) 0.0162(11) 0.0011(9) -0.0010(9) -0.0009(10) C17 0.0220(13) 0.0215(12) 0.0197(12) 0.0014(9) 0.0029(10) -0.0024(10) C2 0.0200(12) 0.0196(12) 0.0162(11) 0.0024(9) 0.0003(9) -0.0040(10) C8 0.0189(12) 0.0223(13) 0.0205(12) 0.0031(9) -0.0021(10) -0.0006(10) C3 0.0198(12) 0.0202(12) 0.0172(12) 0.0027(9) 0.0020(10) -0.0002(10) C23 0.0231(13) 0.0226(13) 0.0204(12) 0.0041(10) 0.0000(10) -0.0007(11) C9 0.0185(12) 0.0200(12) 0.0180(12) 0.0022(9) 0.0024(10) 0.0000(10) C22 0.0315(15) 0.0256(13) 0.0231(13) 0.0004(10) 0.0008(11) 0.0048(12) C10 0.0204(12) 0.0192(12) 0.0151(11) 0.0013(9) -0.0004(9) -0.0035(10) C6 0.0192(13) 0.0246(13) 0.0321(14) 0.0001(11) 0.0009(11) 0.0036(11) C7 0.0241(13) 0.0253(13) 0.0250(13) -0.0037(10) 0.0008(11) 0.0023(11) C24 0.0213(13) 0.0212(13) 0.0194(12) 0.0026(9) 0.0034(10) 0.0005(10) C25 0.0263(13) 0.0191(12) 0.0170(12) 0.0009(9) 0.0025(10) -0.0038(10) C21 0.0291(15) 0.0292(14) 0.0304(14) 0.0030(11) 0.0013(12) 0.0086(12) C4 0.0251(13) 0.0227(13) 0.0172(12) 0.0012(9) -0.0021(10) -0.0039(11) C20 0.0261(14) 0.0292(15) 0.0275(14) 0.0046(11) -0.0065(11) 0.0003(12) C13 0.0218(13) 0.0240(13) 0.0209(12) 0.0020(10) -0.0041(10) -0.0025(11) C18 0.0214(13) 0.0198(12) 0.0199(12) 0.0032(9) 0.0038(10) 0.0017(10) C16 0.0217(13) 0.0208(13) 0.0186(12) -0.0003(9) 0.0016(10) -0.0017(10) C19 0.0268(14) 0.0237(13) 0.0240(13) 0.0015(10) -0.0009(11) -0.0002(11) C5 0.0219(13) 0.0277(14) 0.0226(13) 0.0056(10) -0.0055(10) -0.0015(11) C26 0.0242(13) 0.0227(13) 0.0235(13) -0.0001(10) 0.0012(10) 0.0005(11) C14 0.0192(12) 0.0236(13) 0.0226(13) 0.0016(10) 0.0003(10) 0.0011(10) C28 0.0240(13) 0.0300(14) 0.0184(12) -0.0011(10) -0.0012(10) -0.0058(11) C15 0.0247(13) 0.0196(12) 0.0193(12) -0.0013(9) 0.0033(10) -0.0004(10) C12 0.0269(14) 0.0254(13) 0.0191(12) -0.0047(10) -0.0019(10) 0.0003(11) C30 0.0242(13) 0.0229(13) 0.0242(13) -0.0039(10) 0.0037(10) -0.0016(11) C11 0.0214(13) 0.0236(13) 0.0230(13) -0.0023(10) 0.0013(10) 0.0001(10) C29 0.0198(13) 0.0288(14) 0.0271(14) -0.0013(11) 0.0025(11) -0.0005(11) C27 0.0299(14) 0.0238(13) 0.0210(13) -0.0055(10) 0.0025(11) -0.0038(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9061(16) . ? Cu1 O1 1.9127(16) . ? Cu1 S2 2.2651(7) . ? Cu1 S1 2.2889(7) . ? S1 C2 1.691(2) . ? S2 C17 1.692(2) . ? O1 C1 1.300(3) . ? O2 C9 1.355(3) . ? O2 C8 1.357(3) . ? O4 C24 1.355(3) . ? O4 C23 1.360(3) . ? O3 C16 1.304(3) . ? C1 C9 1.401(3) . ? C1 C2 1.430(3) . ? C17 C16 1.432(3) . ? C17 C18 1.435(3) . ? C2 C3 1.431(3) . ? C8 C3 1.393(3) . ? C8 C7 1.396(3) . ? C3 C4 1.416(3) . ? C23 C22 1.391(4) . ? C23 C18 1.394(3) . ? C9 C10 1.458(3) . ? C22 C21 1.375(4) . ? C10 C15 1.394(3) . ? C10 C11 1.402(3) . ? C6 C7 1.373(3) . ? C6 C5 1.395(3) . ? C24 C16 1.401(3) . ? C24 C25 1.459(3) . ? C25 C30 1.400(4) . ? C25 C26 1.410(3) . ? C21 C20 1.403(4) . ? C4 C5 1.366(3) . ? C20 C19 1.374(4) . ? C13 C12 1.376(3) . ? C13 C14 1.380(3) . ? C18 C19 1.412(3) . ? C26 C27 1.379(3) . ? C14 C15 1.390(3) . ? C28 C27 1.381(4) . ? C28 C29 1.386(3) . ? C12 C11 1.378(3) . ? C30 C29 1.383(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 O3 Cu1 O1 177.60(7) . . ? O3 Cu1 S2 87.95(5) . . ? O1 Cu1 S2 90.90(5) . . ? O3 Cu1 S1 93.97(5) . . ? O1 Cu1 S1 87.11(5) . . ? S2 Cu1 S1 177.21(3) . . ? C2 S1 Cu1 95.61(8) . . ? C17 S2 Cu1 95.55(9) . . ? C1 O1 Cu1 118.50(14) . . ? C9 O2 C8 121.95(19) . . ? C24 O4 C23 122.34(19) . . ? C16 O3 Cu1 118.16(15) . . ? O1 C1 C9 120.9(2) . . ? O1 C1 C2 120.5(2) . . ? C9 C1 C2 118.6(2) . . ? C16 C17 C18 119.2(2) . . ? C16 C17 S2 118.19(18) . . ? C18 C17 S2 122.60(19) . . ? C1 C2 C3 118.7(2) . . ? C1 C2 S1 118.02(18) . . ? C3 C2 S1 123.27(18) . . ? O2 C8 C3 120.9(2) . . ? O2 C8 C7 116.4(2) . . ? C3 C8 C7 122.7(2) . . ? C8 C3 C4 117.0(2) . . ? C8 C3 C2 118.9(2) . . ? C4 C3 C2 124.1(2) . . ? O4 C23 C22 116.2(2) . . ? O4 C23 C18 121.1(2) . . ? C22 C23 C18 122.7(2) . . ? O2 C9 C1 120.8(2) . . ? O2 C9 C10 111.6(2) . . ? C1 C9 C10 127.6(2) . . ? C21 C22 C23 118.3(2) . . ? C15 C10 C11 118.3(2) . . ? C15 C10 C9 122.6(2) . . ? C11 C10 C9 119.1(2) . . ? C7 C6 C5 120.6(2) . . ? C6 C7 C8 118.3(2) . . ? O4 C24 C16 120.5(2) . . ? O4 C24 C25 111.3(2) . . ? C16 C24 C25 128.2(2) . . ? C30 C25 C26 118.1(2) . . ? C30 C25 C24 122.4(2) . . ? C26 C25 C24 119.4(2) . . ? C22 C21 C20 120.7(2) . . ? C5 C4 C3 120.7(2) . . ? C19 C20 C21 120.4(2) . . ? C12 C13 C14 119.6(2) . . ? C23 C18 C19 117.6(2) . . ? C23 C18 C17 118.2(2) . . ? C19 C18 C17 124.2(2) . . ? O3 C16 C24 121.2(2) . . ? O3 C16 C17 120.1(2) . . ? C24 C16 C17 118.7(2) . . ? C20 C19 C18 120.3(2) . . ? C4 C5 C6 120.6(2) . . ? C27 C26 C25 120.2(2) . . ? C13 C14 C15 120.3(2) . . ? C27 C28 C29 119.1(2) . . ? C14 C15 C10 120.5(2) . . ? C13 C12 C11 120.9(2) . . ? C29 C30 C25 120.7(2) . . ? C12 C11 C10 120.5(2) . . ? C30 C29 C28 120.7(2) . . ? C26 C27 C28 121.2(2) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.513 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.084 #===END data_[Zn(3-OHFT)2] _database_code_depnum_ccdc_archive 'CCDC 252677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H20 Cl2 O4 S2 Zn' _chemical_formula_weight 656.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6538(5) _cell_length_b 10.6359(6) _cell_length_c 13.9037(8) _cell_angle_alpha 92.0790(10) _cell_angle_beta 98.5820(10) _cell_angle_gamma 105.6480(10) _cell_volume 1354.89(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6844 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 1.296 _exptl_absorpt_correction_type semi-emperical _exptl_absorpt_correction_T_min 0.814768 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11629 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5904 _reflns_number_gt 5356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+3.2936P] 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 5904 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1393 _refine_ls_goodness_of_fit_ref 1.287 _refine_ls_restrained_S_all 1.287 _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 Cl1 Cl 0.16441(14) 0.30077(16) 0.27203(11) 0.0476(4) Uani 1 1 d . . . O3 O 0.6883(3) 0.2988(3) 0.1346(2) 0.0207(6) Uani 1 1 d . . . Zn1 Zn 0.58402(5) 0.25387(5) 0.24387(3) 0.01836(14) Uani 1 1 d . . . S2 S 0.52564(11) 0.44975(10) 0.23725(7) 0.0197(2) Uani 1 1 d . . . S1 S 0.42526(11) 0.05129(10) 0.25310(7) 0.0205(2) Uani 1 1 d . . . O2 O 0.7127(3) -0.0443(3) 0.5082(2) 0.0182(6) Uani 1 1 d . . . O4 O 0.7488(3) 0.5625(3) -0.0210(2) 0.0179(6) Uani 1 1 d . . . O1 O 0.7159(3) 0.2190(3) 0.3543(2) 0.0199(6) Uani 1 1 d . . . C23 C 0.6896(4) 0.6485(4) 0.0205(3) 0.0193(8) Uani 1 1 d . . . C18 C 0.6203(4) 0.6186(4) 0.1016(3) 0.0177(8) Uani 1 1 d . . . C17 C 0.6141(4) 0.4954(4) 0.1407(3) 0.0174(8) Uani 1 1 d . . . C2 C 0.5359(4) 0.0124(4) 0.3476(3) 0.0185(8) Uani 1 1 d . . . C8 C 0.5884(4) -0.1364(4) 0.4677(3) 0.0180(8) Uani 1 1 d . . . C3 C 0.4971(4) -0.1128(4) 0.3872(3) 0.0175(8) Uani 1 1 d . . . C24 C 0.7473(4) 0.4460(4) 0.0153(3) 0.0158(8) Uani 1 1 d . . . C16 C 0.6835(4) 0.4086(4) 0.0978(3) 0.0160(8) Uani 1 1 d . . . C25 C 0.8200(4) 0.3724(4) -0.0420(3) 0.0172(8) Uani 1 1 d . . . C1 C 0.6717(4) 0.1063(4) 0.3902(3) 0.0167(8) Uani 1 1 d . . . C22 C 0.7010(5) 0.7670(4) -0.0232(3) 0.0231(9) Uani 1 1 d . . . H22 H 0.7489 0.7847 -0.0782 0.028 Uiso 1 1 calc R . . C6 C 0.4330(5) -0.3511(4) 0.4733(3) 0.0252(9) Uani 1 1 d . . . H6 H 0.4097 -0.4319 0.5026 0.030 Uiso 1 1 calc R . . C19 C 0.5601(5) 0.7141(4) 0.1393(3) 0.0219(9) Uani 1 1 d . . . H19 H 0.5116 0.6975 0.1941 0.026 Uiso 1 1 calc R . . C9 C 0.7568(4) 0.0727(4) 0.4708(3) 0.0162(8) Uani 1 1 d . . . C10 C 0.8990(4) 0.1511(4) 0.5232(3) 0.0167(8) Uani 1 1 d . . . C7 C 0.5570(5) -0.2548(4) 0.5118(3) 0.0216(9) Uani 1 1 d . . . H7 H 0.6204 -0.2680 0.5673 0.026 Uiso 1 1 calc R . . C20 C 0.5717(5) 0.8298(4) 0.0972(3) 0.0261(10) Uani 1 1 d . . . H20 H 0.5319 0.8933 0.1236 0.031 Uiso 1 1 calc R . . C26 C 0.8871(4) 0.4306(4) -0.1183(3) 0.0202(8) Uani 1 1 d . . . H26 H 0.8832 0.5161 -0.1333 0.024 Uiso 1 1 calc R . . C27 C 0.9595(5) 0.3640(4) -0.1722(3) 0.0233(9) Uani 1 1 d . . . H27 H 1.0045 0.4043 -0.2238 0.028 Uiso 1 1 calc R . . C4 C 0.3707(5) -0.2147(4) 0.3488(3) 0.0209(9) Uani 1 1 d . . . H4 H 0.3066 -0.2022 0.2934 0.025 Uiso 1 1 calc R . . C5 C 0.3398(5) -0.3314(4) 0.3908(3) 0.0254(9) Uani 1 1 d . . . H5 H 0.2550 -0.3995 0.3640 0.030 Uiso 1 1 calc R . . C30 C 0.8268(5) 0.2464(4) -0.0223(3) 0.0215(9) Uani 1 1 d . . . H30 H 0.7813 0.2049 0.0288 0.026 Uiso 1 1 calc R . . C11 C 0.9787(4) 0.0933(4) 0.5920(3) 0.0205(9) Uani 1 1 d . . . H11 H 0.9386 0.0055 0.6062 0.025 Uiso 1 1 calc R . . C21 C 0.6414(5) 0.8565(4) 0.0154(3) 0.0259(9) Uani 1 1 d . . . H21 H 0.6473 0.9371 -0.0133 0.031 Uiso 1 1 calc R . . C15 C 0.9587(5) 0.2821(4) 0.5060(3) 0.0236(9) Uani 1 1 d . . . H15 H 0.9057 0.3234 0.4604 0.028 Uiso 1 1 calc R . . C28 C 0.9664(5) 0.2402(5) -0.1513(3) 0.0238(9) Uani 1 1 d . . . H28 H 1.0167 0.1956 -0.1880 0.029 Uiso 1 1 calc R . . C12 C 1.1160(5) 0.1641(5) 0.6395(3) 0.0242(9) Uani 1 1 d . . . H12 H 1.1700 0.1237 0.6852 0.029 Uiso 1 1 calc R . . C29 C 0.8997(5) 0.1807(4) -0.0766(3) 0.0252(9) Uani 1 1 d . . . H29 H 0.9036 0.0949 -0.0625 0.030 Uiso 1 1 calc R . . C13 C 1.1752(5) 0.2928(5) 0.6211(3) 0.0259(10) Uani 1 1 d . . . H13 H 1.2699 0.3403 0.6532 0.031 Uiso 1 1 calc R . . C14 C 1.0951(5) 0.3515(5) 0.5555(3) 0.0262(10) Uani 1 1 d . . . H14 H 1.1341 0.4407 0.5442 0.031 Uiso 1 1 calc R . . Cl2 Cl -0.0619(3) 0.07338(14) 0.17850(12) 0.0713(6) Uani 1 1 d . . . C31 C -0.0234(5) 0.2269(5) 0.2414(4) 0.0363(12) Uani 1 1 d . . . H31A H -0.0671 0.2174 0.3017 0.044 Uiso 1 1 calc R . . H31B H -0.0685 0.2842 0.2003 0.044 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 Cl1 0.0231(6) 0.0668(10) 0.0480(8) 0.0221(7) -0.0009(6) 0.0057(6) O3 0.0220(15) 0.0255(16) 0.0188(14) 0.0060(12) 0.0097(12) 0.0097(12) Zn1 0.0173(2) 0.0228(3) 0.0157(2) 0.00305(18) 0.00516(18) 0.00523(19) S2 0.0186(5) 0.0230(5) 0.0176(5) -0.0019(4) 0.0066(4) 0.0044(4) S1 0.0178(5) 0.0240(5) 0.0170(5) -0.0004(4) -0.0011(4) 0.0034(4) O2 0.0152(14) 0.0229(15) 0.0170(14) 0.0004(11) 0.0032(11) 0.0061(12) O4 0.0198(14) 0.0189(14) 0.0167(14) 0.0041(11) 0.0051(11) 0.0069(12) O1 0.0168(14) 0.0233(15) 0.0180(14) 0.0055(12) 0.0023(11) 0.0031(12) C23 0.0152(19) 0.021(2) 0.019(2) -0.0018(16) -0.0010(16) 0.0047(16) C18 0.0121(18) 0.020(2) 0.018(2) -0.0011(16) -0.0016(15) 0.0013(15) C17 0.0095(17) 0.022(2) 0.0178(19) -0.0018(16) 0.0014(15) 0.0008(15) C2 0.020(2) 0.025(2) 0.0130(18) -0.0023(15) 0.0048(15) 0.0093(17) C8 0.0148(19) 0.022(2) 0.0176(19) -0.0018(16) 0.0059(15) 0.0044(16) C3 0.0167(19) 0.017(2) 0.019(2) -0.0024(15) 0.0077(16) 0.0030(15) C24 0.0114(18) 0.019(2) 0.0154(19) -0.0021(15) -0.0016(14) 0.0039(15) C16 0.0117(18) 0.022(2) 0.0139(18) 0.0014(15) 0.0025(14) 0.0036(15) C25 0.0125(18) 0.023(2) 0.0154(19) -0.0020(15) 0.0029(15) 0.0044(16) C1 0.0150(19) 0.019(2) 0.0168(19) -0.0004(15) 0.0046(15) 0.0057(16) C22 0.023(2) 0.024(2) 0.021(2) 0.0015(17) 0.0004(17) 0.0046(17) C6 0.026(2) 0.019(2) 0.033(2) 0.0046(18) 0.0125(19) 0.0069(18) C19 0.020(2) 0.024(2) 0.020(2) -0.0061(17) 0.0000(16) 0.0056(17) C9 0.0142(18) 0.022(2) 0.0139(18) -0.0005(15) 0.0059(15) 0.0065(16) C10 0.0128(18) 0.026(2) 0.0111(18) -0.0037(15) 0.0020(14) 0.0063(16) C7 0.022(2) 0.024(2) 0.022(2) 0.0053(17) 0.0068(17) 0.0104(17) C20 0.023(2) 0.022(2) 0.032(2) -0.0057(18) -0.0029(19) 0.0089(18) C26 0.018(2) 0.024(2) 0.018(2) 0.0011(16) 0.0021(16) 0.0047(17) C27 0.018(2) 0.034(2) 0.016(2) 0.0018(18) 0.0067(16) 0.0023(18) C4 0.019(2) 0.024(2) 0.021(2) -0.0025(16) 0.0044(16) 0.0070(17) C5 0.020(2) 0.025(2) 0.030(2) -0.0043(18) 0.0057(18) 0.0050(18) C30 0.022(2) 0.023(2) 0.022(2) 0.0018(17) 0.0084(17) 0.0070(17) C11 0.020(2) 0.026(2) 0.0142(19) -0.0041(16) 0.0021(16) 0.0066(17) C21 0.027(2) 0.020(2) 0.028(2) 0.0005(18) -0.0026(18) 0.0055(18) C15 0.021(2) 0.025(2) 0.024(2) 0.0007(17) 0.0036(17) 0.0060(18) C28 0.018(2) 0.036(3) 0.019(2) -0.0049(18) 0.0050(17) 0.0121(19) C12 0.018(2) 0.039(3) 0.017(2) -0.0061(18) 0.0011(16) 0.0121(19) C29 0.027(2) 0.023(2) 0.026(2) -0.0012(18) 0.0048(18) 0.0091(18) C13 0.015(2) 0.035(3) 0.025(2) -0.0102(19) 0.0011(17) 0.0036(18) C14 0.021(2) 0.026(2) 0.026(2) -0.0027(18) 0.0037(18) -0.0017(18) Cl2 0.1317(17) 0.0212(7) 0.0466(9) 0.0045(6) -0.0164(10) 0.0135(8) C31 0.023(2) 0.038(3) 0.047(3) -0.008(2) 0.013(2) 0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C31 1.750(5) . ? O3 C16 1.302(5) . ? O3 Zn1 1.949(3) . ? Zn1 O1 1.956(3) . ? Zn1 S2 2.3018(12) . ? Zn1 S1 2.3033(12) . ? S2 C17 1.712(4) . ? S1 C2 1.702(4) . ? O2 C9 1.352(5) . ? O2 C8 1.357(5) . ? O4 C24 1.352(5) . ? O4 C23 1.356(5) . ? O1 C1 1.304(5) . ? C23 C18 1.398(6) . ? C23 C22 1.404(6) . ? C18 C19 1.420(6) . ? C18 C17 1.427(6) . ? C17 C16 1.439(5) . ? C2 C3 1.436(6) . ? C2 C1 1.444(6) . ? C8 C3 1.393(6) . ? C8 C7 1.400(6) . ? C3 C4 1.414(6) . ? C24 C16 1.403(5) . ? C24 C25 1.468(5) . ? C25 C30 1.394(6) . ? C25 C26 1.403(6) . ? C1 C9 1.404(5) . ? C22 C21 1.369(6) . ? C6 C7 1.370(6) . ? C6 C5 1.408(6) . ? C19 C20 1.367(6) . ? C9 C10 1.466(5) . ? C10 C15 1.401(6) . ? C10 C11 1.401(6) . ? C20 C21 1.406(7) . ? C26 C27 1.392(6) . ? C27 C28 1.375(6) . ? C4 C5 1.370(6) . ? C30 C29 1.392(6) . ? C11 C12 1.387(6) . ? C15 C14 1.385(6) . ? C28 C29 1.386(6) . ? C12 C13 1.382(7) . ? C13 C14 1.383(6) . ? Cl2 C31 1.744(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 C16 O3 Zn1 116.1(2) . . ? O3 Zn1 O1 109.61(12) . . ? O3 Zn1 S2 89.01(9) . . ? O1 Zn1 S2 121.82(9) . . ? O3 Zn1 S1 123.42(9) . . ? O1 Zn1 S1 88.97(9) . . ? S2 Zn1 S1 126.19(4) . . ? C17 S2 Zn1 93.64(15) . . ? C2 S1 Zn1 93.75(15) . . ? C9 O2 C8 122.0(3) . . ? C24 O4 C23 121.9(3) . . ? C1 O1 Zn1 115.9(2) . . ? O4 C23 C18 121.1(4) . . ? O4 C23 C22 116.1(4) . . ? C18 C23 C22 122.7(4) . . ? C23 C18 C19 117.1(4) . . ? C23 C18 C17 118.5(4) . . ? C19 C18 C17 124.3(4) . . ? C18 C17 C16 119.0(4) . . ? C18 C17 S2 121.1(3) . . ? C16 C17 S2 119.8(3) . . ? C3 C2 C1 118.5(4) . . ? C3 C2 S1 121.4(3) . . ? C1 C2 S1 120.2(3) . . ? O2 C8 C3 121.3(4) . . ? O2 C8 C7 116.4(4) . . ? C3 C8 C7 122.3(4) . . ? C8 C3 C4 117.6(4) . . ? C8 C3 C2 118.7(4) . . ? C4 C3 C2 123.7(4) . . ? O4 C24 C16 121.1(3) . . ? O4 C24 C25 111.1(3) . . ? C16 C24 C25 127.8(4) . . ? O3 C16 C24 120.5(4) . . ? O3 C16 C17 121.3(3) . . ? C24 C16 C17 118.2(4) . . ? C30 C25 C26 118.3(4) . . ? C30 C25 C24 122.3(4) . . ? C26 C25 C24 119.4(4) . . ? O1 C1 C9 120.4(4) . . ? O1 C1 C2 121.1(4) . . ? C9 C1 C2 118.4(4) . . ? C21 C22 C23 118.3(4) . . ? C7 C6 C5 120.5(4) . . ? C20 C19 C18 120.3(4) . . ? O2 C9 C1 121.0(4) . . ? O2 C9 C10 111.6(3) . . ? C1 C9 C10 127.4(4) . . ? C15 C10 C11 118.7(4) . . ? C15 C10 C9 122.1(4) . . ? C11 C10 C9 119.2(4) . . ? C6 C7 C8 118.6(4) . . ? C19 C20 C21 121.1(4) . . ? C27 C26 C25 120.5(4) . . ? C28 C27 C26 120.5(4) . . ? C5 C4 C3 120.5(4) . . ? C4 C5 C6 120.4(4) . . ? C29 C30 C25 120.7(4) . . ? C12 C11 C10 120.1(4) . . ? C22 C21 C20 120.4(4) . . ? C14 C15 C10 120.1(4) . . ? C27 C28 C29 119.8(4) . . ? C13 C12 C11 120.8(4) . . ? C28 C29 C30 120.2(4) . . ? C12 C13 C14 119.2(4) . . ? C13 C14 C15 120.9(4) . . ? Cl2 C31 Cl1 112.0(3) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 1.054 _refine_diff_density_min -0.920 _refine_diff_density_rms 0.110 #===END data_[Co(3-OHFT)3] _database_code_depnum_ccdc_archive 'CCDC 282322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H27 Co O6 S3' _chemical_formula_weight 818.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 14.0289(7) _cell_length_b 14.0289(7) _cell_length_c 30.796(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5249.0(6) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5023 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.46 _exptl_crystal_description Block _exptl_crystal_colour Black _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.607108 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15047 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2614 _reflns_number_gt 2062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+12.7365P] 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 2614 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Co1 Co 0.6667 0.3333 0.091345(18) 0.01495(15) Uani 1 3 d S . . S1 S 0.57372(5) 0.39620(5) 0.053215(19) 0.01782(15) Uani 1 1 d . . . O1 O 0.54313(13) 0.26713(13) 0.12964(5) 0.0177(4) Uani 1 1 d . . . O2 O 0.34401(13) 0.34072(13) 0.16327(5) 0.0197(4) Uani 1 1 d . . . C2 C 0.47868(19) 0.37106(18) 0.09242(8) 0.0171(5) Uani 1 1 d . . . C3 C 0.39895(19) 0.40615(18) 0.09050(8) 0.0177(5) Uani 1 1 d . . . C4 C 0.3818(2) 0.4579(2) 0.05423(8) 0.0210(5) Uani 1 1 d . . . H4 H 0.4259 0.4722 0.0290 0.025 Uiso 1 1 calc R . . C5 C 0.3021(2) 0.4875(2) 0.05519(9) 0.0251(6) Uani 1 1 d . . . H5 H 0.2908 0.5213 0.0305 0.030 Uiso 1 1 calc R . . C6 C 0.2374(2) 0.4679(2) 0.09242(9) 0.0279(6) Uani 1 1 d . . . H6 H 0.1829 0.4893 0.0929 0.033 Uiso 1 1 calc R . . C7 C 0.2520(2) 0.4181(2) 0.12822(9) 0.0242(6) Uani 1 1 d . . . H7 H 0.2085 0.4052 0.1535 0.029 Uiso 1 1 calc R . . C8 C 0.33208(19) 0.38706(19) 0.12657(8) 0.0187(5) Uani 1 1 d . . . C9 C 0.41771(18) 0.30462(18) 0.16596(8) 0.0176(5) Uani 1 1 d . . . C1 C 0.48115(18) 0.31181(18) 0.12950(8) 0.0168(5) Uani 1 1 d . . . C10 C 0.42243(18) 0.26521(18) 0.20918(8) 0.0173(5) Uani 1 1 d . . . C11 C 0.3542(2) 0.2670(2) 0.24220(8) 0.0220(5) Uani 1 1 d . . . H11 H 0.3046 0.2928 0.2360 0.026 Uiso 1 1 calc R . . C12 C 0.3586(2) 0.2314(2) 0.28349(8) 0.0243(6) Uani 1 1 d . . . H12 H 0.3117 0.2326 0.3055 0.029 Uiso 1 1 calc R . . C13 C 0.4306(2) 0.1938(2) 0.29335(8) 0.0241(6) Uani 1 1 d . . . H13 H 0.4335 0.1698 0.3219 0.029 Uiso 1 1 calc R . . C14 C 0.4981(2) 0.1916(2) 0.26105(8) 0.0236(5) Uani 1 1 d . . . H14 H 0.5475 0.1657 0.2676 0.028 Uiso 1 1 calc R . . C15 C 0.4948(2) 0.22635(19) 0.21943(8) 0.0202(5) Uani 1 1 d . . . H15 H 0.5415 0.2240 0.1976 0.024 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 0.01405(19) 0.01405(19) 0.0167(3) 0.000 0.000 0.00703(9) S1 0.0173(3) 0.0184(3) 0.0185(3) 0.0017(2) 0.0013(2) 0.0095(2) O1 0.0156(8) 0.0181(8) 0.0202(9) 0.0019(7) 0.0025(7) 0.0090(7) O2 0.0164(8) 0.0226(9) 0.0211(9) -0.0011(7) -0.0004(7) 0.0105(7) C2 0.0143(11) 0.0142(11) 0.0188(12) -0.0030(9) -0.0005(9) 0.0041(9) C3 0.0145(11) 0.0145(11) 0.0212(13) -0.0044(9) -0.0028(9) 0.0050(9) C4 0.0206(12) 0.0224(13) 0.0207(13) -0.0028(10) -0.0020(10) 0.0113(11) C5 0.0263(14) 0.0278(14) 0.0258(14) -0.0006(11) -0.0058(11) 0.0170(12) C6 0.0238(13) 0.0327(15) 0.0328(16) -0.0021(12) -0.0023(11) 0.0184(12) C7 0.0192(12) 0.0302(14) 0.0259(14) -0.0013(11) 0.0004(10) 0.0142(11) C8 0.0153(12) 0.0172(12) 0.0222(13) -0.0020(10) -0.0030(9) 0.0071(10) C9 0.0130(11) 0.0138(11) 0.0228(13) -0.0033(9) -0.0005(9) 0.0043(9) C1 0.0127(11) 0.0124(11) 0.0207(12) -0.0027(9) -0.0019(9) 0.0029(9) C10 0.0138(11) 0.0121(11) 0.0200(12) -0.0011(9) 0.0004(9) 0.0020(9) C11 0.0187(12) 0.0195(12) 0.0254(14) -0.0008(10) 0.0006(10) 0.0079(10) C12 0.0228(13) 0.0243(13) 0.0198(13) -0.0012(10) 0.0039(10) 0.0074(11) C13 0.0278(14) 0.0205(13) 0.0188(13) 0.0011(10) -0.0007(10) 0.0082(11) C14 0.0221(13) 0.0211(13) 0.0259(14) 0.0024(10) -0.0002(11) 0.0095(11) C15 0.0188(12) 0.0190(12) 0.0216(13) 0.0002(10) 0.0024(10) 0.0085(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 1.9098(16) 2_655 ? Co1 O1 1.9098(16) 3_665 ? Co1 O1 1.9098(16) . ? Co1 S1 2.2376(7) 2_655 ? Co1 S1 2.2376(7) 3_665 ? Co1 S1 2.2376(7) . ? S1 C2 1.700(2) . ? O1 C1 1.301(3) . ? O2 C8 1.355(3) . ? O2 C9 1.362(3) . ? C2 C1 1.423(3) . ? C2 C3 1.431(3) . ? C3 C8 1.391(3) . ? C3 C4 1.416(3) . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C6 1.402(4) . ? C5 H5 0.9500 . ? C6 C7 1.374(4) . ? C6 H6 0.9500 . ? C7 C8 1.394(3) . ? C7 H7 0.9500 . ? C9 C1 1.405(3) . ? C9 C10 1.455(3) . ? C10 C11 1.406(3) . ? C10 C15 1.407(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 85.88(7) 2_655 3_665 ? O1 Co1 O1 85.88(7) 2_655 . ? O1 Co1 O1 85.88(7) 3_665 . ? O1 Co1 S1 87.12(5) 2_655 2_655 ? O1 Co1 S1 172.75(6) 3_665 2_655 ? O1 Co1 S1 91.74(5) . 2_655 ? O1 Co1 S1 91.74(5) 2_655 3_665 ? O1 Co1 S1 87.12(5) 3_665 3_665 ? O1 Co1 S1 172.75(6) . 3_665 ? S1 Co1 S1 94.98(3) 2_655 3_665 ? O1 Co1 S1 172.75(6) 2_655 . ? O1 Co1 S1 91.74(5) 3_665 . ? O1 Co1 S1 87.12(5) . . ? S1 Co1 S1 94.98(3) 2_655 . ? S1 Co1 S1 94.98(3) 3_665 . ? C2 S1 Co1 95.55(8) . . ? C1 O1 Co1 115.23(14) . . ? C8 O2 C9 121.86(19) . . ? C1 C2 C3 119.1(2) . . ? C1 C2 S1 116.46(18) . . ? C3 C2 S1 124.48(19) . . ? C8 C3 C4 117.2(2) . . ? C8 C3 C2 117.9(2) . . ? C4 C3 C2 124.8(2) . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 118.5(2) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? O2 C8 C3 121.7(2) . . ? O2 C8 C7 115.6(2) . . ? C3 C8 C7 122.7(2) . . ? O2 C9 C1 119.7(2) . . ? O2 C9 C10 112.6(2) . . ? C1 C9 C10 127.6(2) . . ? O1 C1 C9 121.0(2) . . ? O1 C1 C2 120.1(2) . . ? C9 C1 C2 118.9(2) . . ? C11 C10 C15 118.3(2) . . ? C11 C10 C9 119.6(2) . . ? C15 C10 C9 122.1(2) . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.9(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.455 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.074 #===END data_[Ni(3-OHFT)2] _database_code_depnum_ccdc_archive 'CCDC 282323' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H19 Cl3 Ni O4 S2' _chemical_formula_weight 636.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6947(18) _cell_length_b 39.596(9) _cell_length_c 9.965(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.643(3) _cell_angle_gamma 90.00 _cell_volume 2801.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5824 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.37 _exptl_crystal_description Plates _exptl_crystal_colour Green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.326598 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31270 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -50 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6235 _reflns_number_gt 5426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+27.4641P] 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 6235 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2041 _refine_ls_wR_factor_gt 0.1955 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 0.86923(10) 0.080461(19) 0.31043(8) 0.0192(2) Uani 1 1 d . . . S1 S 1.0477(2) 0.05114(4) 0.49444(16) 0.0217(3) Uani 1 1 d . . . S2 S 0.8816(2) 0.04509(4) 0.15040(16) 0.0216(3) Uani 1 1 d . . . O1 O 0.8455(6) 0.11320(11) 0.4372(4) 0.0213(9) Uani 1 1 d . . . O3 O 0.7229(6) 0.10908(10) 0.1614(4) 0.0197(8) Uani 1 1 d . . . O2 O 1.0296(6) 0.12657(11) 0.8247(4) 0.0212(9) Uani 1 1 d . . . O4 O 0.5409(6) 0.10946(10) -0.2305(4) 0.0207(9) Uani 1 1 d . . . C1 C 0.9398(8) 0.10850(16) 0.5775(6) 0.0201(12) Uani 1 1 d . . . C2 C 1.0485(8) 0.07870(15) 0.6268(6) 0.0190(11) Uani 1 1 d . . . C3 C 1.1457(8) 0.07296(15) 0.7797(6) 0.0188(11) Uani 1 1 d . . . C8 C 1.1299(8) 0.09773(15) 0.8753(6) 0.0200(12) Uani 1 1 d . . . C4 C 1.2522(8) 0.04375(16) 0.8423(6) 0.0214(12) Uani 1 1 d . . . H4 H 1.2641 0.0267 0.7824 0.026 Uiso 1 1 calc R . . C16 C 0.6858(8) 0.09966(15) 0.0261(6) 0.0193(12) Uani 1 1 d . . . C18 C 0.7136(8) 0.05777(16) -0.1464(6) 0.0200(12) Uani 1 1 d . . . C17 C 0.7535(8) 0.06839(15) -0.0002(6) 0.0178(11) Uani 1 1 d . . . C19 C 0.7748(8) 0.02705(16) -0.1853(6) 0.0227(12) Uani 1 1 d . . . H19 H 0.8471 0.0122 -0.1132 0.027 Uiso 1 1 calc R . . C9 C 0.9348(8) 0.13232(16) 0.6786(6) 0.0211(12) Uani 1 1 d . . . C23 C 0.6033(8) 0.07924(15) -0.2578(6) 0.0200(12) Uani 1 1 d . . . C28 C 0.3563(9) 0.21817(17) -0.0792(8) 0.0295(14) Uani 1 1 d . . . H28 H 0.3116 0.2399 -0.0762 0.035 Uiso 1 1 calc R . . C6 C 1.3168(8) 0.06567(17) 1.0808(7) 0.0242(13) Uani 1 1 d . . . H6 H 1.3734 0.0629 1.1811 0.029 Uiso 1 1 calc R . . C22 C 0.5572(8) 0.07150(16) -0.4052(6) 0.0210(12) Uani 1 1 d . . . H22 H 0.4877 0.0865 -0.4779 0.025 Uiso 1 1 calc R . . C10 C 0.8381(8) 0.16469(15) 0.6506(6) 0.0190(12) Uani 1 1 d . . . C25 C 0.4981(8) 0.15323(15) -0.0859(6) 0.0187(11) Uani 1 1 d . . . C20 C 0.7282(8) 0.01892(16) -0.3290(7) 0.0234(13) Uani 1 1 d . . . H20 H 0.7696 -0.0013 -0.3538 0.028 Uiso 1 1 calc R . . C7 C 1.2147(8) 0.09442(16) 1.0254(6) 0.0223(12) Uani 1 1 d . . . H7 H 1.2028 0.1112 1.0865 0.027 Uiso 1 1 calc R . . C15 C 0.6853(8) 0.17152(16) 0.5192(7) 0.0235(13) Uani 1 1 d . . . H15 H 0.6460 0.1552 0.4465 0.028 Uiso 1 1 calc R . . C11 C 0.8920(9) 0.18993(16) 0.7578(7) 0.0228(12) Uani 1 1 d . . . H11 H 0.9922 0.1860 0.8457 0.027 Uiso 1 1 calc R . . C5 C 1.3373(9) 0.04045(16) 0.9895(7) 0.0251(13) Uani 1 1 d . . . H5 H 1.4093 0.0214 1.0294 0.030 Uiso 1 1 calc R . . C21 C 0.6175(9) 0.04122(17) -0.4391(7) 0.0262(13) Uani 1 1 d . . . H21 H 0.5849 0.0353 -0.5361 0.031 Uiso 1 1 calc R . . C30 C 0.4929(9) 0.16636(16) 0.0433(7) 0.0259(13) Uani 1 1 d . . . H30 H 0.5375 0.1535 0.1280 0.031 Uiso 1 1 calc R . . C24 C 0.5761(8) 0.12006(15) -0.0907(6) 0.0193(12) Uani 1 1 d . . . C29 C 0.4217(9) 0.19827(17) 0.0447(7) 0.0256(13) Uani 1 1 d . . . H29 H 0.4176 0.2066 0.1307 0.031 Uiso 1 1 calc R . . C26 C 0.4273(9) 0.17328(17) -0.2123(7) 0.0255(13) Uani 1 1 d . . . H26 H 0.4271 0.1649 -0.2996 0.031 Uiso 1 1 calc R . . C14 C 0.5938(9) 0.20210(17) 0.4976(7) 0.0241(13) Uani 1 1 d . . . H14 H 0.4945 0.2063 0.4096 0.029 Uiso 1 1 calc R . . C12 C 0.7988(10) 0.22031(17) 0.7349(7) 0.0291(14) Uani 1 1 d . . . H12 H 0.8375 0.2367 0.8071 0.035 Uiso 1 1 calc R . . C13 C 0.6464(10) 0.22686(17) 0.6043(7) 0.0284(14) Uani 1 1 d . . . H13 H 0.5820 0.2473 0.5895 0.034 Uiso 1 1 calc R . . C27 C 0.3586(10) 0.20518(18) -0.2078(8) 0.0325(15) Uani 1 1 d . . . H27 H 0.3131 0.2182 -0.2920 0.039 Uiso 1 1 calc R . . Cl6 Cl 0.2218(2) 0.14161(5) 0.3743(2) 0.0382(4) Uani 1 1 d . . . C33 C 0.0201(9) 0.16718(16) 0.2953(7) 0.0259(13) Uani 1 1 d . . . H33 H -0.0891 0.1551 0.2992 0.031 Uiso 1 1 calc R . . Cl2 Cl -0.0190(3) 0.17533(5) 0.11117(19) 0.0377(4) Uani 1 1 d . . . Cl1 Cl 0.0472(3) 0.20551(5) 0.3905(2) 0.0421(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0180(4) 0.0243(4) 0.0140(4) -0.0017(3) 0.0046(3) 0.0010(3) S1 0.0223(7) 0.0263(7) 0.0156(7) -0.0014(6) 0.0065(5) 0.0029(6) S2 0.0214(7) 0.0249(7) 0.0161(7) -0.0013(6) 0.0045(5) 0.0026(6) O1 0.022(2) 0.028(2) 0.0132(19) -0.0017(16) 0.0059(16) 0.0055(17) O3 0.023(2) 0.025(2) 0.0114(19) -0.0014(16) 0.0067(16) 0.0008(16) O2 0.019(2) 0.026(2) 0.015(2) 0.0005(16) 0.0026(16) 0.0017(16) O4 0.022(2) 0.025(2) 0.0129(19) -0.0024(16) 0.0046(16) 0.0001(17) C1 0.018(3) 0.030(3) 0.015(3) -0.001(2) 0.010(2) -0.001(2) C2 0.016(3) 0.025(3) 0.019(3) -0.002(2) 0.009(2) -0.001(2) C3 0.014(3) 0.027(3) 0.018(3) -0.002(2) 0.009(2) -0.002(2) C8 0.015(3) 0.028(3) 0.021(3) 0.001(2) 0.012(2) -0.002(2) C4 0.018(3) 0.029(3) 0.020(3) -0.001(2) 0.010(2) -0.001(2) C16 0.013(3) 0.026(3) 0.021(3) -0.005(2) 0.009(2) -0.002(2) C18 0.011(2) 0.031(3) 0.018(3) -0.005(2) 0.006(2) -0.004(2) C17 0.013(2) 0.026(3) 0.016(3) -0.003(2) 0.008(2) -0.004(2) C19 0.021(3) 0.029(3) 0.017(3) -0.002(2) 0.006(2) -0.001(2) C9 0.018(3) 0.030(3) 0.016(3) 0.000(2) 0.006(2) -0.002(2) C23 0.015(3) 0.026(3) 0.020(3) -0.005(2) 0.008(2) -0.003(2) C28 0.026(3) 0.025(3) 0.035(4) 0.000(3) 0.010(3) -0.001(3) C6 0.016(3) 0.041(4) 0.016(3) 0.004(3) 0.008(2) 0.001(2) C22 0.017(3) 0.030(3) 0.018(3) -0.001(2) 0.010(2) -0.003(2) C10 0.019(3) 0.025(3) 0.014(3) -0.001(2) 0.007(2) -0.003(2) C25 0.014(3) 0.026(3) 0.016(3) -0.002(2) 0.006(2) -0.002(2) C20 0.020(3) 0.029(3) 0.024(3) -0.004(2) 0.011(2) 0.000(2) C7 0.023(3) 0.032(3) 0.013(3) 0.002(2) 0.008(2) -0.002(2) C15 0.021(3) 0.028(3) 0.019(3) -0.005(2) 0.006(2) 0.000(2) C11 0.022(3) 0.030(3) 0.020(3) 0.000(2) 0.012(2) -0.004(2) C5 0.020(3) 0.028(3) 0.027(3) 0.003(3) 0.009(2) 0.004(2) C21 0.024(3) 0.035(3) 0.017(3) -0.009(3) 0.005(2) -0.003(3) C30 0.026(3) 0.030(3) 0.019(3) -0.002(2) 0.005(2) 0.002(3) C24 0.018(3) 0.030(3) 0.013(3) -0.002(2) 0.010(2) -0.006(2) C29 0.024(3) 0.035(3) 0.021(3) -0.005(3) 0.013(2) 0.002(3) C26 0.030(3) 0.032(3) 0.021(3) 0.000(3) 0.016(3) 0.001(3) C14 0.022(3) 0.036(3) 0.017(3) 0.002(3) 0.010(2) 0.006(3) C12 0.033(3) 0.029(3) 0.024(3) -0.006(3) 0.010(3) -0.005(3) C13 0.034(4) 0.025(3) 0.025(3) 0.003(3) 0.010(3) 0.004(3) C27 0.035(4) 0.032(4) 0.031(4) 0.008(3) 0.013(3) 0.007(3) Cl6 0.0249(8) 0.0387(9) 0.0423(10) -0.0018(8) 0.0033(7) 0.0034(7) C33 0.023(3) 0.028(3) 0.024(3) -0.004(3) 0.006(2) 0.000(2) Cl2 0.0399(9) 0.0467(10) 0.0282(9) 0.0035(7) 0.0149(7) -0.0042(8) Cl1 0.0457(10) 0.0366(10) 0.0469(11) -0.0153(8) 0.0213(9) -0.0036(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O3 1.863(4) . ? Ni1 O1 1.867(4) . ? Ni1 S2 2.1518(17) . ? Ni1 S1 2.1580(17) . ? S1 C2 1.710(6) . ? S2 C17 1.714(6) . ? O1 C1 1.317(7) . ? O3 C16 1.320(7) . ? O2 C8 1.362(7) . ? O2 C9 1.373(7) . ? O4 C23 1.355(7) . ? O4 C24 1.378(7) . ? C1 C9 1.392(8) . ? C1 C2 1.420(8) . ? C2 C3 1.433(8) . ? C3 C8 1.405(8) . ? C3 C4 1.416(8) . ? C8 C7 1.389(8) . ? C4 C5 1.363(9) . ? C16 C24 1.401(8) . ? C16 C17 1.406(8) . ? C18 C23 1.396(8) . ? C18 C19 1.411(9) . ? C18 C17 1.432(8) . ? C19 C20 1.374(8) . ? C9 C10 1.454(8) . ? C23 C22 1.406(8) . ? C28 C29 1.386(9) . ? C28 C27 1.388(10) . ? C6 C7 1.373(9) . ? C6 C5 1.401(9) . ? C22 C21 1.374(9) . ? C10 C11 1.404(8) . ? C10 C15 1.409(8) . ? C25 C30 1.403(8) . ? C25 C26 1.409(8) . ? C25 C24 1.452(8) . ? C20 C21 1.410(9) . ? C15 C14 1.375(9) . ? C11 C12 1.374(9) . ? C30 C29 1.379(9) . ? C26 C27 1.377(9) . ? C14 C13 1.387(9) . ? C12 C13 1.401(9) . ? Cl6 C33 1.764(7) . ? C33 Cl1 1.759(7) . ? C33 Cl2 1.771(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Ni1 O1 86.01(18) . . ? O3 Ni1 S2 89.47(13) . . ? O1 Ni1 S2 175.47(14) . . ? O3 Ni1 S1 175.05(14) . . ? O1 Ni1 S1 89.69(13) . . ? S2 Ni1 S1 94.83(6) . . ? C2 S1 Ni1 97.1(2) . . ? C17 S2 Ni1 97.1(2) . . ? C1 O1 Ni1 117.6(4) . . ? C16 O3 Ni1 118.0(4) . . ? C8 O2 C9 121.7(5) . . ? C23 O4 C24 121.7(5) . . ? O1 C1 C9 121.0(5) . . ? O1 C1 C2 119.7(5) . . ? C9 C1 C2 119.3(5) . . ? C1 C2 C3 119.7(5) . . ? C1 C2 S1 115.9(4) . . ? C3 C2 S1 124.3(5) . . ? C8 C3 C4 117.3(5) . . ? C8 C3 C2 117.7(5) . . ? C4 C3 C2 125.0(5) . . ? O2 C8 C7 116.2(5) . . ? O2 C8 C3 121.3(5) . . ? C7 C8 C3 122.5(6) . . ? C5 C4 C3 120.6(6) . . ? O3 C16 C24 120.7(5) . . ? O3 C16 C17 119.3(5) . . ? C24 C16 C17 120.0(5) . . ? C23 C18 C19 118.1(5) . . ? C23 C18 C17 117.2(5) . . ? C19 C18 C17 124.7(6) . . ? C16 C17 C18 119.9(5) . . ? C16 C17 S2 116.1(4) . . ? C18 C17 S2 124.0(5) . . ? C20 C19 C18 120.5(6) . . ? O2 C9 C1 120.2(5) . . ? O2 C9 C10 112.0(5) . . ? C1 C9 C10 127.8(5) . . ? O4 C23 C18 122.2(5) . . ? O4 C23 C22 115.8(5) . . ? C18 C23 C22 122.0(6) . . ? C29 C28 C27 118.9(6) . . ? C7 C6 C5 121.3(6) . . ? C21 C22 C23 118.3(6) . . ? C11 C10 C15 117.8(6) . . ? C11 C10 C9 120.1(5) . . ? C15 C10 C9 122.0(5) . . ? C30 C25 C26 118.3(6) . . ? C30 C25 C24 121.6(5) . . ? C26 C25 C24 120.1(5) . . ? C19 C20 C21 120.1(6) . . ? C6 C7 C8 118.1(6) . . ? C14 C15 C10 120.5(6) . . ? C12 C11 C10 121.0(6) . . ? C4 C5 C6 120.2(6) . . ? C22 C21 C20 121.0(6) . . ? C29 C30 C25 120.1(6) . . ? O4 C24 C16 119.0(5) . . ? O4 C24 C25 112.7(5) . . ? C16 C24 C25 128.2(5) . . ? C30 C29 C28 121.4(6) . . ? C27 C26 C25 120.6(6) . . ? C15 C14 C13 121.4(6) . . ? C11 C12 C13 120.9(6) . . ? C14 C13 C12 118.3(6) . . ? C26 C27 C28 120.8(6) . . ? Cl6 C33 Cl1 110.7(3) . . ? Cl6 C33 Cl2 109.7(4) . . ? Cl1 C33 Cl2 109.8(4) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.810 _refine_diff_density_min -0.718 _refine_diff_density_rms 0.134