# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Travis J. Williams' _publ_contact_author_email travisw@usc.edu loop_ _publ_contact_author_address 'Loker Hydrocarbon Research Institute and Department of Chemistry' 'University of Southern California, Los Angeles, CA 90089-1661' loop_ _publ_author_address 'Loker Hydrocarbon Research Institute and Department of Chemistry' 'University of Southern California, Los Angeles, CA 90089-1661' loop_ _publ_section_title 'Copper-Catalyzed Oxidation of Azolines to Azoles' _publ_section_abstract 'no abstract' _publ_section_comment 'CCDC 761476' _publ_section_references 'See main text' loop_ _publ_author_name A.C.Dawsey V.Li K.C.Hamilton J.Wang T.J.Williams #============================================================================== data_I _database_code_depnum_ccdc_archive 'CCDC 761476' #TrackingRef '- 761476.cif' _chemical_name_systematic ? _chemical_name_common CuOTf _chemical_formula_moiety 'C24 H22 Cu N2 O3, 2(C F3 O3 S)' _chemical_formula_sum 'C26 H22 Cu F6 N2 O9 S2' _chemical_formula_iupac ? _chemical_formula_weight 748.13 _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.5620(12) _cell_length_b 26.689(4) _cell_length_c 26.774(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 6118.2(15) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3761 _cell_measurement_theta_min 2.7456 _cell_measurement_theta_max 22.1961 _cell_measurement_temperature 148.(2) _exptl_crystal_description plate _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3032 _exptl_absorpt_coefficient_mu 0.941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS V2008/1' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.75 _exptl_special_details ; ; _diffrn_ambient_temperature 148.(2) _diffrn_source 'fine-focus tube' _diffrn_source_type ? _diffrn_radiation_type 'MoK\a ' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method 'omega- and phi-scans' _diffrn_detector_area_resol_mean 8.3660 _diffrn_reflns_number 36207 _diffrn_reflns_av_R_equivalents 0.1122 _diffrn_reflns_av_sigmaI/netI 0.1150 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.43 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_max 0.938 _diffrn_measured_fraction_theta_full 0.938 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 31 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogen positions of the water ligands were found in the electron density map. The O-H and H-H distances were restrained during refinement to 0.84 and 1.44 A, respectively. ; _reflns_number_total 7239 _reflns_number_gt 3996 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_gt 0.1210 _refine_ls_wR_factor_ref 0.1452 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.007 _refine_ls_number_reflns 7239 _refine_ls_number_parameters 439 _refine_ls_number_restraints 47 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+4.3205P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.871 _refine_diff_density_min -0.708 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'APEX2 v2010.11-3 (Bruker AXS)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'Bruker SHELXT' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.9368(5) 0.08160(15) 0.08229(15) 0.0297(10) Uani d . 1 . . H H1 0.9164 0.0568 0.1058 0.036 Uiso calc R 1 . . C C2 0.9986(5) 0.06784(16) 0.03665(15) 0.0320(10) Uani d . 1 . . H H2 1.0204 0.0342 0.0307 0.038 Uiso calc R 1 . . C C3 1.0290(4) 0.10247(15) -0.00035(14) 0.0282(9) Uani d . 1 . . C C4 1.0052(4) 0.15390(15) 0.01240(13) 0.0241(8) Uani d . 1 . . C C5 0.9448(4) 0.16500(14) 0.05980(13) 0.0224(8) Uani d . 1 . . C C6 1.0489(5) 0.19549(15) -0.01850(14) 0.0283(9) Uani d . 1 . . H H6 1.0907 0.1893 -0.05 0.034 Uiso calc R 1 . . C C7 1.0311(5) 0.24330(15) -0.00325(14) 0.0286(9) Uani d . 1 . . H H7 1.062 0.2691 -0.0244 0.034 Uiso calc R 1 . . C C8 0.9659(4) 0.25558(14) 0.04458(13) 0.0236(9) Uani d . 1 . . C C9 0.9245(4) 0.21538(14) 0.07598(13) 0.0224(8) Uani d . 1 . . C C10 0.9475(4) 0.30476(14) 0.06375(14) 0.0249(9) Uani d . 1 . . C C11 0.8903(5) 0.30985(15) 0.11197(14) 0.0266(9) Uani d . 1 . . H H11 0.8762 0.3417 0.1254 0.032 Uiso calc R 1 . . C C12 0.8539(4) 0.26794(15) 0.14053(14) 0.0267(9) Uani d . 1 . . H H12 0.8164 0.2725 0.1728 0.032 Uiso calc R 1 . . C C13 1.0827(5) 0.08697(15) -0.05057(14) 0.0279(9) Uani d . 1 . . C C14 1.2082(5) 0.05411(15) -0.05578(15) 0.0320(10) Uani d . 1 . . H H14 1.2598 0.0423 -0.0276 0.038 Uiso calc R 1 . . C C15 1.2561(5) 0.03912(15) -0.10270(15) 0.0350(10) Uani d . 1 . . H H15 1.3409 0.0176 -0.1059 0.042 Uiso calc R 1 . . C C16 1.1793(5) 0.05584(16) -0.14508(16) 0.0371(11) Uani d . 1 . . H H16 1.2114 0.0454 -0.1766 0.044 Uiso calc R 1 . . C C17 1.0550(5) 0.08806(17) -0.14015(16) 0.0389(11) Uani d . 1 . . H H17 1.0025 0.0993 -0.1684 0.047 Uiso calc R 1 . . C C18 1.0075(5) 0.10396(17) -0.09332(15) 0.0350(10) Uani d . 1 . . H H18 0.9245 0.1262 -0.0905 0.042 Uiso calc R 1 . . C C19 0.9864(5) 0.35019(15) 0.03390(14) 0.0286(9) Uani d . 1 . . C C20 0.9280(5) 0.35649(16) -0.01428(15) 0.0315(10) Uani d . 1 . . H H20 0.8647 0.332 -0.0285 0.038 Uiso calc R 1 . . C C21 0.9649(5) 0.39953(17) -0.04099(16) 0.0409(11) Uani d . 1 . . H H21 0.9253 0.404 -0.073 0.049 Uiso calc R 1 . . C C22 1.0595(6) 0.43538(18) -0.02032(19) 0.0458(13) Uani d . 1 . . H H22 1.084 0.4641 -0.0385 0.055 Uiso calc R 1 . . C C23 1.1184(5) 0.42926(17) 0.02690(19) 0.0442(12) Uani d . 1 . . H H23 1.1838 0.4536 0.0404 0.053 Uiso calc R 1 . . C C24 1.0813(5) 0.38697(16) 0.05477(16) 0.0355(10) Uani d . 1 . . H H24 1.1196 0.3833 0.0871 0.043 Uiso calc R 1 . . C C25 0.3451(7) 0.2617(3) 0.1554(2) 0.0724(16) Uani d U 1 . . C C26 0.3386(6) -0.02783(18) 0.19487(17) 0.0420(11) Uani d U 1 . . Cu Cu1 0.82049(5) 0.156882(18) 0.156979(16) 0.02494(14) Uani d . 1 . . F F1 0.4628(5) 0.28868(14) 0.17456(17) 0.1072(14) Uani d U 1 . . F F2 0.3081(4) 0.28299(16) 0.11146(16) 0.1121(16) Uani d U 1 . . F F3 0.2228(4) 0.26968(13) 0.18555(14) 0.0868(11) Uani d U 1 . . F F4 0.3103(4) -0.04866(11) 0.15088(11) 0.0725(10) Uani d U 1 . . F F5 0.2277(4) -0.04337(12) 0.22510(10) 0.0674(9) Uani d U 1 . . F F6 0.4721(4) -0.04518(13) 0.21049(16) 0.1004(13) Uani d U 1 . . N N1 0.9054(4) 0.12895(12) 0.09370(11) 0.0243(7) Uani d . 1 . . N N2 0.8707(3) 0.22154(11) 0.12329(11) 0.0219(7) Uani d . 1 . . O O1 0.7418(4) 0.09051(12) 0.17787(11) 0.0345(7) Uani d D 1 . . O O2 0.7348(3) 0.19127(11) 0.21622(10) 0.0289(7) Uani d D 1 . . O O3 1.0418(3) 0.14346(13) 0.19978(12) 0.0365(7) Uani d D 1 . . O O4 0.4145(3) 0.18234(12) 0.20021(10) 0.0410(8) Uani d U 1 . . O O5 0.5325(4) 0.19691(16) 0.11981(11) 0.0635(11) Uani d U 1 . . O O6 0.2534(4) 0.17758(15) 0.12604(11) 0.0617(11) Uani d U 1 . . O O7 0.4683(4) 0.04793(11) 0.15463(11) 0.0429(8) Uani d U 1 . . O O8 0.1898(4) 0.05172(15) 0.17164(17) 0.0818(13) Uani d U 1 . . O O9 0.3778(5) 0.05587(14) 0.23916(13) 0.0710(12) Uani d U 1 . . S S1 0.39186(13) 0.19781(5) 0.14915(4) 0.0457(3) Uani d U 1 . . S S2 0.34123(14) 0.03965(4) 0.18870(4) 0.0401(3) Uani d U 1 . . H H1O 0.6465(15) 0.0842(19) 0.1739(15) 0.063(18) Uiso d D 1 . . H H2O 0.782(4) 0.0844(18) 0.2059(8) 0.057(17) Uiso d D 1 . . H H3O 0.786(4) 0.1834(17) 0.2417(10) 0.058(16) Uiso d D 1 . . H H4O 0.6403(14) 0.1828(15) 0.2167(14) 0.040(14) Uiso d D 1 . . H H5O 1.120(4) 0.1482(18) 0.1816(17) 0.08(2) Uiso d D 1 . . H H6O 1.036(7) 0.1143(8) 0.211(2) 0.11(3) Uiso d D 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.035(2) 0.030(2) 0.024(2) -0.0067(19) 0.0022(18) 0.0025(17) C2 0.042(3) 0.028(2) 0.026(2) -0.0025(19) 0.000(2) -0.0012(18) C3 0.022(2) 0.036(2) 0.027(2) -0.0008(18) -0.0013(17) -0.0052(19) C4 0.019(2) 0.032(2) 0.0217(19) 0.0009(17) -0.0004(15) -0.0021(17) C5 0.0170(19) 0.029(2) 0.022(2) 0.0009(16) -0.0022(15) -0.0003(16) C6 0.030(2) 0.035(3) 0.020(2) 0.0031(19) 0.0040(17) 0.0020(17) C7 0.028(2) 0.033(2) 0.024(2) 0.0029(18) 0.0072(18) 0.0037(18) C8 0.020(2) 0.031(2) 0.020(2) 0.0034(17) 0.0003(16) 0.0037(17) C9 0.016(2) 0.031(2) 0.020(2) -0.0010(16) -0.0014(15) -0.0017(16) C10 0.017(2) 0.032(2) 0.026(2) 0.0008(17) 0.0011(16) 0.0015(17) C11 0.026(2) 0.024(2) 0.030(2) 0.0017(17) -0.0010(17) -0.0005(17) C12 0.023(2) 0.038(3) 0.020(2) -0.0017(18) 0.0041(16) -0.0021(17) C13 0.030(2) 0.030(2) 0.024(2) -0.0075(19) 0.0019(17) -0.0051(17) C14 0.034(3) 0.031(2) 0.031(2) -0.0001(19) 0.0013(19) 0.0010(18) C15 0.041(3) 0.029(2) 0.035(2) 0.001(2) 0.010(2) -0.0070(19) C16 0.041(3) 0.042(3) 0.028(2) -0.001(2) 0.009(2) -0.0100(19) C17 0.039(3) 0.052(3) 0.025(2) -0.002(2) -0.0078(19) -0.004(2) C18 0.027(2) 0.047(3) 0.031(2) 0.001(2) -0.0001(19) -0.003(2) C19 0.027(2) 0.028(2) 0.031(2) 0.0080(18) 0.0089(18) 0.0017(17) C20 0.031(2) 0.036(3) 0.028(2) 0.0031(19) 0.0079(18) 0.0036(18) C21 0.045(3) 0.044(3) 0.034(3) 0.007(2) 0.009(2) 0.007(2) C22 0.049(3) 0.035(3) 0.054(3) -0.001(2) 0.015(2) 0.016(2) C23 0.035(3) 0.036(3) 0.062(3) -0.003(2) 0.006(2) 0.005(2) C24 0.030(2) 0.038(3) 0.038(3) -0.002(2) 0.000(2) 0.000(2) C25 0.036(3) 0.103(4) 0.078(4) -0.013(3) -0.001(3) 0.035(3) C26 0.039(3) 0.046(3) 0.042(3) -0.007(2) -0.001(2) 0.002(2) Cu1 0.0256(3) 0.0309(3) 0.0183(2) -0.0041(2) 0.0026(2) 0.0015(2) F1 0.075(3) 0.075(3) 0.172(4) -0.014(2) -0.024(3) 0.015(2) F2 0.070(3) 0.141(4) 0.126(3) -0.008(2) -0.013(2) 0.094(3) F3 0.066(2) 0.078(3) 0.116(3) 0.0255(19) 0.009(2) 0.021(2) F4 0.097(3) 0.061(2) 0.0590(19) -0.0299(18) 0.0213(18) -0.0293(15) F5 0.079(2) 0.077(2) 0.0465(17) -0.0334(18) 0.0148(16) 0.0065(15) F6 0.063(2) 0.072(2) 0.166(4) 0.0075(19) -0.026(2) 0.046(2) N1 0.0242(18) 0.028(2) 0.0203(17) -0.0027(14) 0.0005(14) 0.0016(14) N2 0.0178(17) 0.0284(19) 0.0195(17) -0.0024(13) 0.0023(13) -0.0016(14) O1 0.0350(19) 0.0388(18) 0.0296(17) -0.0108(15) -0.0003(15) 0.0073(14) O2 0.0208(16) 0.0464(19) 0.0196(15) 0.0003(14) -0.0015(12) 0.0009(13) O3 0.0250(18) 0.049(2) 0.0351(18) 0.0023(14) -0.0041(14) -0.0045(15) O4 0.0248(16) 0.077(2) 0.0212(15) 0.0083(15) 0.0008(12) 0.0075(14) O5 0.0250(18) 0.138(4) 0.0279(17) -0.0152(19) 0.0035(14) -0.0024(19) O6 0.0256(17) 0.127(3) 0.0324(18) -0.0181(19) -0.0028(14) 0.0070(19) O7 0.0464(19) 0.048(2) 0.0345(17) -0.0145(15) 0.0045(15) -0.0012(15) O8 0.040(2) 0.073(3) 0.133(4) 0.013(2) -0.011(2) 0.009(2) O9 0.078(3) 0.082(3) 0.053(2) -0.030(2) 0.029(2) -0.038(2) S1 0.0226(6) 0.0905(10) 0.0240(6) -0.0064(6) -0.0006(5) 0.0094(6) S2 0.0342(7) 0.0391(7) 0.0470(7) -0.0003(5) 0.0055(5) -0.0038(5) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 . 1.328(5) ? C1 C2 . 1.381(5) ? C1 H1 . 0.93 ? C2 C3 . 1.380(5) ? C2 H2 . 0.93 ? C3 C4 . 1.429(5) ? C3 C13 . 1.480(5) ? C4 C5 . 1.402(5) ? C4 C6 . 1.434(5) ? C5 N1 . 1.365(5) ? C5 C9 . 1.423(5) ? C6 C7 . 1.349(5) ? C6 H6 . 0.93 ? C7 C8 . 1.435(5) ? C7 H7 . 0.93 ? C8 C9 . 1.408(5) ? C8 C10 . 1.418(5) ? C9 N2 . 1.358(4) ? C10 C11 . 1.387(5) ? C10 C19 . 1.490(5) ? C11 C12 . 1.390(5) ? C11 H11 . 0.93 ? C12 N2 . 1.330(5) ? C12 H12 . 0.93 ? C13 C18 . 1.389(5) ? C13 C14 . 1.394(6) ? C14 C15 . 1.381(5) ? C14 H14 . 0.93 ? C15 C16 . 1.386(6) ? C15 H15 . 0.93 ? C16 C17 . 1.374(6) ? C16 H16 . 0.93 ? C17 C18 . 1.385(6) ? C17 H17 . 0.93 ? C18 H18 . 0.93 ? C19 C24 . 1.392(6) ? C19 C20 . 1.394(5) ? C20 C21 . 1.390(6) ? C20 H20 . 0.93 ? C21 C22 . 1.370(6) ? C21 H21 . 0.93 ? C22 C23 . 1.371(7) ? C22 H22 . 0.93 ? C23 C24 . 1.390(6) ? C23 H23 . 0.93 ? C24 H24 . 0.93 ? C25 F3 . 1.339(6) ? C25 F1 . 1.339(7) ? C25 F2 . 1.345(6) ? C25 S1 . 1.761(7) ? C26 F6 . 1.302(5) ? C26 F5 . 1.314(5) ? C26 F4 . 1.325(5) ? C26 S2 . 1.809(5) ? Cu1 O2 . 1.974(3) ? Cu1 O1 . 1.976(3) ? Cu1 N1 . 1.989(3) ? Cu1 N2 . 1.994(3) ? Cu1 O3 . 2.243(3) ? O1 H1O . 0.8400(11) ? O1 H2O . 0.8399(11) ? O2 H3O . 0.8400(11) ? O2 H4O . 0.8401(10) ? O3 H5O . 0.8400(11) ? O3 H6O . 0.8400(10) ? O4 S1 . 1.441(3) ? O5 S1 . 1.438(3) ? O6 S1 . 1.442(3) ? O7 S2 . 1.436(3) ? O8 S2 . 1.412(4) ? O9 S2 . 1.453(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 C1 C2 . . 122.3(4) ? N1 C1 H1 . . 118.8 ? C2 C1 H1 . . 118.8 ? C3 C2 C1 . . 122.0(4) ? C3 C2 H2 . . 119.0 ? C1 C2 H2 . . 119.0 ? C2 C3 C4 . . 116.4(4) ? C2 C3 C13 . . 121.6(4) ? C4 C3 C13 . . 122.0(4) ? C5 C4 C3 . . 118.1(3) ? C5 C4 C6 . . 117.1(3) ? C3 C4 C6 . . 124.6(3) ? N1 C5 C4 . . 123.0(3) ? N1 C5 C9 . . 115.7(3) ? C4 C5 C9 . . 121.3(3) ? C7 C6 C4 . . 121.9(4) ? C7 C6 H6 . . 119.1 ? C4 C6 H6 . . 119.1 ? C6 C7 C8 . . 122.0(4) ? C6 C7 H7 . . 119.0 ? C8 C7 H7 . . 119.0 ? C9 C8 C10 . . 117.5(3) ? C9 C8 C7 . . 117.2(3) ? C10 C8 C7 . . 125.3(3) ? N2 C9 C8 . . 123.4(3) ? N2 C9 C5 . . 116.1(3) ? C8 C9 C5 . . 120.5(3) ? C11 C10 C8 . . 117.8(3) ? C11 C10 C19 . . 119.9(3) ? C8 C10 C19 . . 122.3(3) ? C10 C11 C12 . . 120.8(4) ? C10 C11 H11 . . 119.6 ? C12 C11 H11 . . 119.6 ? N2 C12 C11 . . 122.3(4) ? N2 C12 H12 . . 118.9 ? C11 C12 H12 . . 118.9 ? C18 C13 C14 . . 118.7(4) ? C18 C13 C3 . . 120.9(4) ? C14 C13 C3 . . 120.4(4) ? C15 C14 C13 . . 120.1(4) ? C15 C14 H14 . . 119.9 ? C13 C14 H14 . . 119.9 ? C14 C15 C16 . . 120.7(4) ? C14 C15 H15 . . 119.6 ? C16 C15 H15 . . 119.6 ? C17 C16 C15 . . 119.4(4) ? C17 C16 H16 . . 120.3 ? C15 C16 H16 . . 120.3 ? C16 C17 C18 . . 120.4(4) ? C16 C17 H17 . . 119.8 ? C18 C17 H17 . . 119.8 ? C17 C18 C13 . . 120.7(4) ? C17 C18 H18 . . 119.7 ? C13 C18 H18 . . 119.7 ? C24 C19 C20 . . 119.7(4) ? C24 C19 C10 . . 119.3(4) ? C20 C19 C10 . . 120.9(4) ? C21 C20 C19 . . 119.6(4) ? C21 C20 H20 . . 120.2 ? C19 C20 H20 . . 120.2 ? C22 C21 C20 . . 120.3(4) ? C22 C21 H21 . . 119.9 ? C20 C21 H21 . . 119.9 ? C21 C22 C23 . . 120.4(4) ? C21 C22 H22 . . 119.8 ? C23 C22 H22 . . 119.8 ? C22 C23 C24 . . 120.5(5) ? C22 C23 H23 . . 119.7 ? C24 C23 H23 . . 119.7 ? C23 C24 C19 . . 119.4(4) ? C23 C24 H24 . . 120.3 ? C19 C24 H24 . . 120.3 ? F3 C25 F1 . . 105.9(6) ? F3 C25 F2 . . 106.0(5) ? F1 C25 F2 . . 106.6(5) ? F3 C25 S1 . . 112.9(4) ? F1 C25 S1 . . 112.7(4) ? F2 C25 S1 . . 112.2(5) ? F6 C26 F5 . . 108.9(4) ? F6 C26 F4 . . 107.3(4) ? F5 C26 F4 . . 106.4(4) ? F6 C26 S2 . . 111.9(3) ? F5 C26 S2 . . 112.3(3) ? F4 C26 S2 . . 109.8(3) ? O2 Cu1 O1 . . 93.60(12) ? O2 Cu1 N1 . . 174.13(12) ? O1 Cu1 N1 . . 91.70(13) ? O2 Cu1 N2 . . 92.37(12) ? O1 Cu1 N2 . . 167.78(13) ? N1 Cu1 N2 . . 81.96(12) ? O2 Cu1 O3 . . 88.73(11) ? O1 Cu1 O3 . . 90.00(13) ? N1 Cu1 O3 . . 93.81(12) ? N2 Cu1 O3 . . 100.79(13) ? C1 N1 C5 . . 117.9(3) ? C1 N1 Cu1 . . 128.8(3) ? C5 N1 Cu1 . . 113.1(2) ? C12 N2 C9 . . 118.3(3) ? C12 N2 Cu1 . . 128.7(3) ? C9 N2 Cu1 . . 113.0(2) ? Cu1 O1 H1O . . 118.(3) ? Cu1 O1 H2O . . 107.(3) ? H1O O1 H2O . . 118.(2) ? Cu1 O2 H3O . . 110.(3) ? Cu1 O2 H4O . . 104.(3) ? H3O O2 H4O . . 115.(2) ? Cu1 O3 H5O . . 111.(4) ? Cu1 O3 H6O . . 107.(4) ? H5O O3 H6O . . 114.(2) ? O5 S1 O4 . . 113.64(19) ? O5 S1 O6 . . 116.6(2) ? O4 S1 O6 . . 114.2(2) ? O5 S1 C25 . . 105.0(3) ? O4 S1 C25 . . 102.5(2) ? O6 S1 C25 . . 102.5(3) ? O8 S2 O7 . . 117.0(2) ? O8 S2 O9 . . 115.5(3) ? O7 S2 O9 . . 112.4(2) ? O8 S2 C26 . . 104.2(2) ? O7 S2 C26 . . 102.8(2) ? O9 S2 C26 . . 102.4(2) ? _publ_section_abstract 'No abstract' _publ_section_comment 'CCDC 761477' _publ_section_references 'See main text' #============================================================================== data_II _database_code_depnum_ccdc_archive 'CCDC 761477' #TrackingRef '- 761477.cif' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C22 H34 Cu N2 O3, 2(C F3 O3 S)' _chemical_formula_sum 'C24 H34 Cu F6 N2 O9 S2' _chemical_formula_iupac ? _chemical_formula_weight 736.20 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4067(13) _cell_length_b 12.5305(15) _cell_length_c 12.5733(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.443(2) _cell_angle_gamma 90.00 _cell_volume 1639.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 3372 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 758 _exptl_absorpt_coefficient_mu 0.876 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.877 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(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_reflns_number 10158 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5429 _reflns_number_gt 4322 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0505P)^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 0.000(14) _refine_ls_number_reflns 5429 _refine_ls_number_parameters 429 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7483(5) 0.5853(4) 0.0304(3) 0.0345(11) Uani 1 1 d . . . C2 C 0.7788(5) 0.5453(4) -0.0692(3) 0.0355(11) Uani 1 1 d . . . H2 H 0.7483 0.4777 -0.0900 0.043 Uiso 1 1 calc R . . C3 C 0.8537(5) 0.6038(4) -0.1382(4) 0.0430(13) Uani 1 1 d . . . C4 C 0.9008(5) 0.7015(4) -0.1055(3) 0.0417(14) Uani 1 1 d . . . H4 H 0.9530 0.7402 -0.1517 0.050 Uiso 1 1 calc R . . C5 C 0.8740(4) 0.7454(4) -0.0063(3) 0.0338(11) Uani 1 1 d . . . C6 C 0.7955(3) 0.6863(5) 0.0597(3) 0.0273(9) Uani 1 1 d . . . C7 C 0.6664(5) 0.5206(4) 0.1049(4) 0.0399(12) Uani 1 1 d . . . H7A H 0.6390 0.4553 0.0698 0.060 Uiso 1 1 calc R . . H7B H 0.5915 0.5619 0.1238 0.060 Uiso 1 1 calc R . . H7C H 0.7163 0.5033 0.1688 0.060 Uiso 1 1 calc R . . C8 C 0.8849(6) 0.5591(5) -0.2478(4) 0.0579(17) Uani 1 1 d . . . H8A H 0.9774 0.5532 -0.2539 0.087 Uiso 1 1 calc R . . H8B H 0.8512 0.6067 -0.3026 0.087 Uiso 1 1 calc R . . H8C H 0.8461 0.4892 -0.2564 0.087 Uiso 1 1 calc R . . C9 C 0.9279(5) 0.8534(4) 0.0258(4) 0.0457(13) Uani 1 1 d . . . H9A H 0.8937 0.8742 0.0938 0.068 Uiso 1 1 calc R . . H9B H 0.9037 0.9060 -0.0276 0.068 Uiso 1 1 calc R . . H9C H 1.0209 0.8491 0.0319 0.068 Uiso 1 1 calc R . . N1 N 0.7624(3) 0.7243(3) 0.1630(2) 0.0272(8) Uani 1 1 d . . . C10 C 0.6736(4) 0.7924(4) 0.1737(3) 0.0287(10) Uani 1 1 d . . . C11 C 0.6402(4) 0.8202(4) 0.2869(3) 0.0299(10) Uani 1 1 d . . . N2 N 0.7086(3) 0.7715(3) 0.3573(3) 0.0257(8) Uani 1 1 d . . . C14 C 0.6845(4) 0.7857(4) 0.4692(3) 0.0304(11) Uani 1 1 d . . . C15 C 0.6233(4) 0.7016(4) 0.5211(3) 0.0334(12) Uani 1 1 d . . . C16 C 0.6031(5) 0.7148(5) 0.6297(3) 0.0448(14) Uani 1 1 d . . . H16 H 0.5634 0.6596 0.6673 0.054 Uiso 1 1 calc R . . C17 C 0.6395(5) 0.8060(6) 0.6835(3) 0.0507(16) Uani 1 1 d . . . C18 C 0.7004(5) 0.8866(5) 0.6293(4) 0.0491(15) Uani 1 1 d . . . H18 H 0.7260 0.9484 0.6666 0.059 Uiso 1 1 calc R . . C19 C 0.7256(4) 0.8791(4) 0.5198(4) 0.0355(11) Uani 1 1 d . . . C20 C 0.7879(5) 0.9697(4) 0.4637(4) 0.0495(14) Uani 1 1 d . . . H20A H 0.8517 0.9421 0.4159 0.074 Uiso 1 1 calc R . . H20B H 0.8292 1.0166 0.5155 0.074 Uiso 1 1 calc R . . H20C H 0.7233 1.0093 0.4231 0.074 Uiso 1 1 calc R . . C21 C 0.6100(6) 0.8204(7) 0.8003(4) 0.074(2) Uani 1 1 d . . . H21A H 0.5348 0.8654 0.8068 0.110 Uiso 1 1 calc R . . H21B H 0.6829 0.8536 0.8367 0.110 Uiso 1 1 calc R . . H21C H 0.5936 0.7513 0.8320 0.110 Uiso 1 1 calc R . . C22 C 0.5754(5) 0.6064(4) 0.4631(4) 0.0494(14) Uani 1 1 d . . . H22A H 0.5083 0.6274 0.4124 0.074 Uiso 1 1 calc R . . H22B H 0.5410 0.5557 0.5132 0.074 Uiso 1 1 calc R . . H22C H 0.6456 0.5736 0.4256 0.074 Uiso 1 1 calc R . . C13 C 0.5331(5) 0.8946(4) 0.3076(4) 0.0414(13) Uani 1 1 d . . . H13A H 0.5191 0.8981 0.3835 0.062 Uiso 1 1 calc R . . H13B H 0.4555 0.8693 0.2714 0.062 Uiso 1 1 calc R . . H13C H 0.5544 0.9650 0.2814 0.062 Uiso 1 1 calc R . . C12 C 0.5986(5) 0.8454(4) 0.0837(3) 0.0395(12) Uani 1 1 d . . . H12A H 0.6265 0.9188 0.0767 0.059 Uiso 1 1 calc R . . H12B H 0.5076 0.8438 0.0987 0.059 Uiso 1 1 calc R . . H12C H 0.6134 0.8074 0.0179 0.059 Uiso 1 1 calc R . . C23 C 0.7329(6) 0.2858(5) 0.3892(5) 0.0567(16) Uani 1 1 d . . . C24 C 0.7179(5) 0.1667(6) 0.9691(5) 0.0653(18) Uani 1 1 d . . . Cu1 Cu 0.84755(4) 0.67862(8) 0.29990(3) 0.02751(14) Uani 1 1 d . . . F1 F 0.7107(3) 0.2129(3) 0.3154(3) 0.0757(11) Uani 1 1 d . . . F2 F 0.6962(4) 0.2464(3) 0.4808(3) 0.0822(12) Uani 1 1 d . . . F3 F 0.6605(3) 0.3705(3) 0.3657(4) 0.0814(12) Uani 1 1 d . . . F4 F 0.8364(4) 0.1515(4) 1.0058(4) 0.1058(16) Uani 1 1 d . . . F5 F 0.6732(5) 0.2511(4) 1.0168(3) 0.0885(14) Uani 1 1 d . . . F6 F 0.6505(5) 0.0857(4) 0.9973(4) 0.124(2) Uani 1 1 d . . . O1 O 0.8883(3) 0.6148(2) 0.4412(2) 0.0347(8) Uani 1 1 d D . . O2 O 0.9550(3) 0.5727(3) 0.2288(2) 0.0338(7) Uani 1 1 d D . . O3 O 1.0029(3) 0.7980(3) 0.3145(2) 0.0368(8) Uani 1 1 d D . . O4 O 0.7897(5) 0.0930(4) 0.7880(5) 0.0932(19) Uani 1 1 d . . . O5 O 0.5825(3) 0.1795(4) 0.7954(3) 0.0540(9) Uani 1 1 d . . . O6 O 0.7774(4) 0.2845(3) 0.8089(3) 0.0571(11) Uani 1 1 d . . . O7 O 0.9649(4) 0.2235(3) 0.4171(3) 0.0554(10) Uani 1 1 d . . . O8 O 0.9081(4) 0.3988(3) 0.4834(3) 0.0498(10) Uani 1 1 d . . . O9 O 0.9239(4) 0.3686(3) 0.2945(3) 0.0508(10) Uani 1 1 d . . . S1 S 0.90139(12) 0.32311(12) 0.39649(9) 0.0392(3) Uani 1 1 d . . . S2 S 0.71604(11) 0.18284(16) 0.82385(11) 0.0533(3) Uani 1 1 d . . . H5O H 1.027(3) 0.820(3) 0.3739(14) 0.023(11) Uiso 1 1 d D . . H6O H 1.056(3) 0.788(5) 0.267(3) 0.07(2) Uiso 1 1 d D . . H2O H 0.901(5) 0.5501(8) 0.451(4) 0.051(18) Uiso 1 1 d D . . H1O H 0.941(4) 0.659(3) 0.464(5) 0.11(3) Uiso 1 1 d D . . H3O H 0.937(4) 0.5132(19) 0.254(4) 0.053(19) Uiso 1 1 d D . . H4O H 1.0316(15) 0.591(4) 0.227(6) 0.10(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.040(3) 0.035(3) 0.029(2) 0.002(2) 0.0040(19) 0.006(2) C2 0.044(3) 0.029(3) 0.034(2) -0.004(2) 0.000(2) 0.011(2) C3 0.054(3) 0.038(3) 0.037(3) -0.002(2) 0.007(2) 0.015(3) C4 0.045(3) 0.044(4) 0.037(2) 0.008(2) 0.0153(19) 0.005(3) C5 0.038(3) 0.031(3) 0.033(2) 0.005(2) 0.0053(19) 0.003(2) C6 0.0295(19) 0.026(2) 0.0264(17) -0.002(2) 0.0022(14) 0.004(3) C7 0.039(3) 0.039(3) 0.042(3) -0.001(2) 0.004(2) -0.005(2) C8 0.088(5) 0.051(4) 0.036(3) -0.003(2) 0.021(3) 0.016(3) C9 0.050(3) 0.046(4) 0.041(3) 0.006(2) 0.006(2) -0.010(3) N1 0.0285(19) 0.026(2) 0.0270(17) 0.0007(15) 0.0031(14) 0.0001(17) C10 0.035(2) 0.025(3) 0.026(2) 0.0001(18) 0.0049(17) 0.002(2) C11 0.032(2) 0.025(3) 0.033(2) 0.000(2) 0.0054(17) -0.003(2) N2 0.0251(19) 0.026(2) 0.0262(16) -0.0020(15) 0.0051(14) 0.0006(16) C14 0.027(2) 0.035(3) 0.029(2) -0.005(2) -0.0016(17) 0.007(2) C15 0.034(2) 0.038(4) 0.0294(19) 0.000(2) 0.0045(16) 0.006(2) C16 0.040(3) 0.058(4) 0.036(2) 0.008(2) 0.0113(19) 0.016(3) C17 0.046(3) 0.080(5) 0.026(2) -0.003(3) 0.000(2) 0.026(3) C18 0.050(3) 0.057(4) 0.039(3) -0.026(3) -0.014(2) 0.018(3) C19 0.029(2) 0.036(3) 0.042(2) -0.011(2) 0.0029(19) 0.006(2) C20 0.046(3) 0.041(4) 0.061(3) -0.017(3) -0.003(2) 0.005(3) C21 0.072(4) 0.119(6) 0.030(3) -0.013(3) -0.002(2) 0.038(4) C22 0.055(3) 0.039(4) 0.055(3) 0.004(3) 0.019(3) -0.010(3) C13 0.042(3) 0.044(3) 0.038(2) -0.005(2) -0.002(2) 0.017(3) C12 0.046(3) 0.045(3) 0.028(2) 0.009(2) 0.003(2) 0.012(3) C23 0.045(3) 0.046(4) 0.078(4) 0.004(3) -0.006(3) -0.007(3) C24 0.050(3) 0.045(5) 0.100(4) 0.032(4) -0.014(3) -0.004(4) Cu1 0.0305(2) 0.0260(3) 0.0262(2) 0.0011(3) 0.00244(16) 0.0034(3) F1 0.072(2) 0.051(3) 0.102(3) -0.0142(19) -0.0211(18) -0.0101(18) F2 0.076(3) 0.080(3) 0.092(3) 0.010(2) 0.026(2) -0.021(2) F3 0.050(2) 0.049(2) 0.144(3) -0.001(2) -0.019(2) 0.0113(18) F4 0.061(2) 0.105(4) 0.149(4) 0.016(3) -0.034(2) 0.006(2) F5 0.110(4) 0.097(4) 0.059(2) 0.013(2) 0.012(2) 0.026(3) F6 0.115(4) 0.115(4) 0.140(4) 0.076(4) -0.033(3) -0.057(4) O1 0.047(2) 0.027(2) 0.0296(16) 0.0016(15) -0.0028(13) -0.0007(18) O2 0.037(2) 0.027(2) 0.0367(17) 0.0032(15) 0.0062(14) 0.0048(16) O3 0.0389(19) 0.036(2) 0.0352(17) -0.0018(16) 0.0062(15) -0.0072(16) O4 0.043(3) 0.057(3) 0.181(5) -0.065(3) 0.021(3) -0.007(2) O5 0.0356(16) 0.059(2) 0.068(2) -0.008(2) 0.0142(14) -0.002(2) O6 0.062(3) 0.045(3) 0.065(2) -0.015(2) 0.022(2) -0.014(2) O7 0.062(2) 0.039(2) 0.065(2) 0.0058(17) -0.0107(18) 0.0114(19) O8 0.068(3) 0.036(2) 0.0447(19) 0.0076(16) -0.0093(17) -0.0007(19) O9 0.073(3) 0.037(2) 0.0418(18) 0.0086(16) 0.0015(17) -0.0032(19) S1 0.0429(7) 0.0306(8) 0.0436(6) 0.0073(5) -0.0067(5) -0.0008(6) S2 0.0347(6) 0.0413(8) 0.0846(9) -0.0153(10) 0.0158(5) -0.0035(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.393(6) . ? C1 C6 1.403(7) . ? C1 C7 1.517(7) . ? C2 C3 1.390(7) . ? C3 C4 1.378(7) . ? C3 C8 1.530(7) . ? C4 C5 1.397(6) . ? C5 C6 1.392(6) . ? C5 C9 1.517(7) . ? C6 N1 1.434(5) . ? N1 C10 1.268(5) . ? N1 Cu1 1.999(3) . ? C10 C12 1.512(6) . ? C10 C11 1.514(6) . ? C11 N2 1.277(5) . ? C11 C13 1.481(7) . ? N2 C14 1.447(5) . ? N2 Cu1 2.004(4) . ? C14 C19 1.394(7) . ? C14 C15 1.402(6) . ? C15 C16 1.396(6) . ? C15 C22 1.479(7) . ? C16 C17 1.376(8) . ? C17 C18 1.382(8) . ? C17 C21 1.518(7) . ? C18 C19 1.412(7) . ? C19 C20 1.493(7) . ? C23 F2 1.318(7) . ? C23 F1 1.318(7) . ? C23 F3 1.331(7) . ? C23 S1 1.815(6) . ? C24 F6 1.289(7) . ? C24 F5 1.307(8) . ? C24 F4 1.319(6) . ? C24 S2 1.837(7) . ? Cu1 O2 1.965(3) . ? Cu1 O1 1.985(3) . ? Cu1 O3 2.206(3) . ? O4 S2 1.441(5) . ? O5 S2 1.427(3) . ? O6 S2 1.439(4) . ? O7 S1 1.433(4) . ? O8 S1 1.447(4) . ? O9 S1 1.428(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 C2 C1 C6 118.3(4) . . ? C2 C1 C7 120.5(5) . . ? C6 C1 C7 121.2(4) . . ? C3 C2 C1 121.0(5) . . ? C4 C3 C2 118.9(4) . . ? C4 C3 C8 120.8(5) . . ? C2 C3 C8 120.3(5) . . ? C3 C4 C5 122.6(5) . . ? C6 C5 C4 117.2(5) . . ? C6 C5 C9 122.3(4) . . ? C4 C5 C9 120.5(4) . . ? C5 C6 C1 122.0(4) . . ? C5 C6 N1 121.5(5) . . ? C1 C6 N1 116.5(4) . . ? C10 N1 C6 120.8(3) . . ? C10 N1 Cu1 114.2(3) . . ? C6 N1 Cu1 125.0(3) . . ? N1 C10 C12 125.5(4) . . ? N1 C10 C11 116.1(4) . . ? C12 C10 C11 118.5(4) . . ? N2 C11 C13 126.1(4) . . ? N2 C11 C10 113.8(4) . . ? C13 C11 C10 120.1(4) . . ? C11 N2 C14 120.5(4) . . ? C11 N2 Cu1 115.0(3) . . ? C14 N2 Cu1 124.5(3) . . ? C19 C14 C15 123.8(4) . . ? C19 C14 N2 119.2(4) . . ? C15 C14 N2 116.9(4) . . ? C16 C15 C14 116.6(4) . . ? C16 C15 C22 121.4(5) . . ? C14 C15 C22 121.9(4) . . ? C17 C16 C15 122.2(5) . . ? C16 C17 C18 119.2(4) . . ? C16 C17 C21 120.9(6) . . ? C18 C17 C21 119.8(6) . . ? C17 C18 C19 122.1(5) . . ? C14 C19 C18 116.0(5) . . ? C14 C19 C20 123.7(4) . . ? C18 C19 C20 120.3(4) . . ? F2 C23 F1 107.9(5) . . ? F2 C23 F3 108.5(5) . . ? F1 C23 F3 108.0(5) . . ? F2 C23 S1 110.7(4) . . ? F1 C23 S1 111.5(4) . . ? F3 C23 S1 110.3(4) . . ? F6 C24 F5 108.0(6) . . ? F6 C24 F4 107.5(5) . . ? F5 C24 F4 107.3(6) . . ? F6 C24 S2 111.6(5) . . ? F5 C24 S2 111.8(4) . . ? F4 C24 S2 110.5(5) . . ? O2 Cu1 O1 91.39(14) . . ? O2 Cu1 N1 92.66(14) . . ? O1 Cu1 N1 165.05(15) . . ? O2 Cu1 N2 168.43(15) . . ? O1 Cu1 N2 92.96(14) . . ? N1 Cu1 N2 80.53(14) . . ? O2 Cu1 O3 94.11(15) . . ? O1 Cu1 O3 93.39(14) . . ? N1 Cu1 O3 100.66(13) . . ? N2 Cu1 O3 96.32(14) . . ? O9 S1 O7 115.1(2) . . ? O9 S1 O8 114.2(2) . . ? O7 S1 O8 114.9(2) . . ? O9 S1 C23 103.7(3) . . ? O7 S1 C23 103.0(3) . . ? O8 S1 C23 103.6(3) . . ? O5 S2 O6 115.2(3) . . ? O5 S2 O4 114.9(3) . . ? O6 S2 O4 114.2(3) . . ? O5 S2 C24 103.4(2) . . ? O6 S2 C24 103.5(3) . . ? O4 S2 C24 103.5(4) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.562 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.067