# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 _publ_section_title ; Helical Coordination Polymers and Cyclic Dimers Formed from Heteroleptic Thioether-Dipyrrinato Copper(II) Complexes ; _publ_contact_author_name 'Prof Seth Cohen' _publ_contact_author_address ; Department of Chemistry and Biochemistry U.C. San Diego 9500 Gilman Drive MC 0358 La Jolla CA 92093-0358 UNITED STATES OF AMERICA ; _publ_contact_author_email SCOHEN@UCSD.EDU _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name _publ_author_address S.M.Cohen ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; L.Do ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; S.R.Halper ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; #========================================================================= data_[Cu(4-mtdpm)2] _database_code_depnum_ccdc_archive 'CCDC 246586' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H26 Cu N4 S2' _chemical_formula_weight 594.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.082(2) _cell_length_b 8.9956(11) _cell_length_c 32.899(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5351.4(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9135 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.816964 _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 31345 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 27.57 _reflns_number_total 6028 _reflns_number_gt 5444 _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^)+(0.0415P)^2^+4.5253P] 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 6028 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.002 _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 0.74861(11) 0.8888(2) 0.22093(6) 0.0171(4) Uani 1 1 d . . . H1 H 0.7735 0.8494 0.1979 0.021 Uiso 1 1 calc R . . C2 C 0.78013(11) 0.8996(2) 0.25985(6) 0.0185(4) Uani 1 1 d . . . H2 H 0.8283 0.8691 0.2677 0.022 Uiso 1 1 calc R . . C3 C 0.72702(11) 0.9632(2) 0.28424(6) 0.0171(4) Uani 1 1 d . . . H3 H 0.7319 0.9864 0.3123 0.021 Uiso 1 1 calc R . . C4 C 0.66346(11) 0.9879(2) 0.25972(6) 0.0146(4) Uani 1 1 d . . . C5 C 0.59516(11) 1.0487(2) 0.27188(6) 0.0144(4) Uani 1 1 d . . . C6 C 0.53626(11) 1.0799(2) 0.24546(6) 0.0156(4) Uani 1 1 d . . . C7 C 0.46312(11) 1.1239(2) 0.25624(6) 0.0189(4) Uani 1 1 d . . . H7 H 0.4451 1.1411 0.2829 0.023 Uiso 1 1 calc R . . C8 C 0.42354(11) 1.1367(2) 0.22067(6) 0.0193(4) Uani 1 1 d . . . H8 H 0.3731 1.1646 0.2180 0.023 Uiso 1 1 calc R . . C9 C 0.47305(11) 1.1001(2) 0.18904(6) 0.0176(4) Uani 1 1 d . . . H9 H 0.4603 1.0997 0.1610 0.021 Uiso 1 1 calc R . . C10 C 0.58313(11) 1.0767(2) 0.31595(6) 0.0154(4) Uani 1 1 d . . . C11 C 0.59433(11) 0.9625(2) 0.34403(6) 0.0168(4) Uani 1 1 d . . . H11 H 0.6103 0.8678 0.3347 0.020 Uiso 1 1 calc R . . C12 C 0.58249(12) 0.9849(2) 0.38533(6) 0.0177(4) Uani 1 1 d . . . H12 H 0.5897 0.9054 0.4039 0.021 Uiso 1 1 calc R . . C13 C 0.56008(11) 1.1233(2) 0.39946(6) 0.0170(4) Uani 1 1 d . . . C14 C 0.54750(11) 1.2386(2) 0.37154(6) 0.0192(4) Uani 1 1 d . . . H14 H 0.5311 1.3329 0.3809 0.023 Uiso 1 1 calc R . . C15 C 0.55890(11) 1.2153(2) 0.33044(6) 0.0180(4) Uani 1 1 d . . . H15 H 0.5502 1.2940 0.3118 0.022 Uiso 1 1 calc R . . C16 C 0.58436(13) 1.0004(2) 0.47621(6) 0.0221(4) Uani 1 1 d . . . H16A H 0.5530 0.9149 0.4695 0.033 Uiso 1 1 calc R . . H16B H 0.5846 1.0156 0.5057 0.033 Uiso 1 1 calc R . . H16C H 0.6349 0.9817 0.4668 0.033 Uiso 1 1 calc R . . C17 C 0.67668(11) 0.6740(2) 0.15388(6) 0.0173(4) Uani 1 1 d . . . H17 H 0.6788 0.6500 0.1820 0.021 Uiso 1 1 calc R . . C18 C 0.69372(12) 0.5732(2) 0.12245(6) 0.0194(4) Uani 1 1 d . . . H18 H 0.7092 0.4729 0.1253 0.023 Uiso 1 1 calc R . . C19 C 0.68328(11) 0.6502(2) 0.08667(6) 0.0182(4) Uani 1 1 d . . . H19 H 0.6901 0.6124 0.0600 0.022 Uiso 1 1 calc R . . C20 C 0.66039(10) 0.7969(2) 0.09711(6) 0.0153(4) Uani 1 1 d . . . C21 C 0.64208(10) 0.9131(2) 0.07045(6) 0.0147(4) Uani 1 1 d . . . C22 C 0.61564(10) 1.0540(2) 0.08236(6) 0.0154(4) Uani 1 1 d . . . C23 C 0.60445(11) 1.1814(2) 0.05733(6) 0.0161(4) Uani 1 1 d . . . H23 H 0.6107 1.1864 0.0287 0.019 Uiso 1 1 calc R . . C24 C 0.58285(11) 1.2961(2) 0.08245(6) 0.0189(4) Uani 1 1 d . . . H24 H 0.5712 1.3950 0.0746 0.023 Uiso 1 1 calc R . . C25 C 0.58156(11) 1.2373(2) 0.12209(6) 0.0181(4) Uani 1 1 d . . . H25 H 0.5688 1.2928 0.1456 0.022 Uiso 1 1 calc R . . C26 C 0.65163(11) 0.8889(2) 0.02605(6) 0.0146(4) Uani 1 1 d . . . C27 C 0.71961(11) 0.8503(2) 0.00892(6) 0.0189(4) Uani 1 1 d . . . H27 H 0.7607 0.8309 0.0261 0.023 Uiso 1 1 calc R . . C28 C 0.72797(11) 0.8400(2) -0.03313(6) 0.0191(4) Uani 1 1 d . . . H28 H 0.7745 0.8129 -0.0444 0.023 Uiso 1 1 calc R . . C29 C 0.66846(11) 0.8693(2) -0.05867(6) 0.0164(4) Uani 1 1 d . . . C30 C 0.59958(11) 0.9017(2) -0.04174(6) 0.0172(4) Uani 1 1 d . . . H30 H 0.5581 0.9172 -0.0589 0.021 Uiso 1 1 calc R . . C31 C 0.59158(11) 0.9112(2) -0.00013(6) 0.0164(4) Uani 1 1 d . . . H31 H 0.5444 0.9333 0.0110 0.020 Uiso 1 1 calc R . . C32 C 0.75409(12) 0.7635(3) -0.12310(6) 0.0260(5) Uani 1 1 d . . . H32A H 0.7982 0.8134 -0.1125 0.039 Uiso 1 1 calc R . . H32B H 0.7589 0.7508 -0.1526 0.039 Uiso 1 1 calc R . . H32C H 0.7490 0.6659 -0.1102 0.039 Uiso 1 1 calc R . . Cu1 Cu 0.619909(13) 0.97616(3) 0.171510(7) 0.01361(8) Uani 1 1 d . . . N1 N 0.67919(9) 0.94086(18) 0.22025(5) 0.0147(3) Uani 1 1 d . . . N2 N 0.54032(9) 1.06593(18) 0.20346(5) 0.0148(3) Uani 1 1 d . . . N3 N 0.65711(9) 0.80779(18) 0.13939(5) 0.0152(3) Uani 1 1 d . . . N4 N 0.60071(9) 1.09275(18) 0.12250(5) 0.0160(3) Uani 1 1 d . . . S1 S 0.54848(3) 1.16444(6) 0.451519(15) 0.02262(12) Uani 1 1 d . . . S2 S 0.67394(3) 0.87384(6) -0.112258(15) 0.02010(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0173(9) 0.0170(9) 0.0170(9) -0.0001(7) 0.0018(8) 0.0022(8) C2 0.0167(9) 0.0178(10) 0.0211(10) 0.0014(8) -0.0041(8) 0.0009(8) C3 0.0195(10) 0.0155(9) 0.0164(9) 0.0008(7) -0.0035(8) -0.0002(7) C4 0.0183(10) 0.0117(9) 0.0137(9) 0.0017(7) 0.0003(7) -0.0017(7) C5 0.0180(9) 0.0104(9) 0.0150(9) 0.0010(7) 0.0013(7) -0.0017(7) C6 0.0187(10) 0.0143(9) 0.0137(9) 0.0020(7) 0.0025(7) 0.0002(7) C7 0.0186(10) 0.0213(10) 0.0169(9) 0.0025(8) 0.0042(8) 0.0005(8) C8 0.0148(9) 0.0185(10) 0.0247(10) 0.0041(8) 0.0007(8) 0.0012(7) C9 0.0197(10) 0.0150(9) 0.0181(9) 0.0034(7) -0.0031(8) -0.0005(8) C10 0.0166(9) 0.0170(9) 0.0127(9) -0.0006(7) 0.0000(7) -0.0011(7) C11 0.0214(10) 0.0137(9) 0.0154(9) -0.0019(7) 0.0005(8) -0.0006(8) C12 0.0221(10) 0.0170(10) 0.0139(9) 0.0013(7) 0.0021(8) -0.0009(8) C13 0.0177(10) 0.0199(10) 0.0135(9) -0.0014(7) 0.0032(7) -0.0011(8) C14 0.0215(10) 0.0159(9) 0.0202(10) -0.0026(8) 0.0030(8) 0.0038(8) C15 0.0208(10) 0.0151(9) 0.0182(9) 0.0019(7) 0.0002(8) 0.0024(8) C16 0.0298(12) 0.0219(11) 0.0145(9) 0.0003(8) 0.0009(8) 0.0015(9) C17 0.0169(9) 0.0181(10) 0.0169(9) 0.0032(8) -0.0011(7) 0.0002(8) C18 0.0221(10) 0.0161(9) 0.0200(10) 0.0004(8) -0.0015(8) 0.0027(8) C19 0.0195(10) 0.0185(10) 0.0165(9) -0.0022(8) -0.0008(8) 0.0031(8) C20 0.0141(9) 0.0172(9) 0.0145(9) -0.0002(7) -0.0007(7) 0.0001(7) C21 0.0109(8) 0.0196(9) 0.0136(9) 0.0000(7) -0.0009(7) 0.0001(7) C22 0.0137(9) 0.0189(10) 0.0135(9) 0.0021(7) -0.0002(7) -0.0010(7) C23 0.0158(9) 0.0184(10) 0.0141(9) 0.0030(7) -0.0011(7) -0.0026(7) C24 0.0216(10) 0.0156(9) 0.0196(10) 0.0033(8) -0.0011(8) -0.0010(8) C25 0.0217(10) 0.0168(10) 0.0158(9) -0.0006(7) 0.0012(8) 0.0013(8) C26 0.0153(9) 0.0146(9) 0.0140(9) 0.0008(7) 0.0000(7) 0.0005(7) C27 0.0155(9) 0.0248(11) 0.0164(9) -0.0004(8) -0.0025(7) 0.0024(8) C28 0.0154(9) 0.0244(11) 0.0174(9) -0.0023(8) 0.0023(8) 0.0003(8) C29 0.0219(10) 0.0148(9) 0.0127(8) -0.0004(7) 0.0001(7) -0.0030(7) C30 0.0174(9) 0.0190(10) 0.0151(9) -0.0004(7) -0.0033(7) 0.0000(8) C31 0.0162(9) 0.0158(9) 0.0172(9) 0.0009(7) 0.0007(7) 0.0023(8) C32 0.0252(11) 0.0327(12) 0.0202(10) -0.0063(9) 0.0049(9) 0.0010(9) Cu1 0.01587(13) 0.01471(13) 0.01026(12) 0.00082(8) -0.00010(9) 0.00246(9) N1 0.0155(8) 0.0160(8) 0.0127(7) 0.0015(6) 0.0004(6) 0.0011(6) N2 0.0159(8) 0.0163(8) 0.0120(7) 0.0009(6) -0.0005(6) 0.0019(6) N3 0.0166(8) 0.0154(8) 0.0135(7) 0.0008(6) -0.0001(6) 0.0005(6) N4 0.0190(8) 0.0152(8) 0.0137(8) 0.0009(6) 0.0003(6) 0.0008(6) S1 0.0336(3) 0.0207(3) 0.0135(2) -0.00234(19) 0.0053(2) 0.0040(2) S2 0.0261(3) 0.0212(3) 0.0130(2) -0.00050(18) 0.00062(19) -0.0003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.340(3) . ? C1 C2 1.405(3) . ? C2 C3 1.376(3) . ? C3 C4 1.422(3) . ? C4 N1 1.395(2) . ? C4 C5 1.409(3) . ? C5 C6 1.403(3) . ? C5 C10 1.488(3) . ? C6 N2 1.389(2) . ? C6 C7 1.425(3) . ? C7 C8 1.376(3) . ? C8 C9 1.412(3) . ? C9 N2 1.341(2) . ? C10 C11 1.397(3) . ? C10 C15 1.405(3) . ? C11 C12 1.390(3) . ? C12 C13 1.390(3) . ? C13 C14 1.404(3) . ? C13 S1 1.7649(19) . ? C14 C15 1.384(3) . ? C16 S1 1.805(2) . ? C17 N3 1.342(2) . ? C17 C18 1.409(3) . ? C18 C19 1.379(3) . ? C19 C20 1.425(3) . ? C20 N3 1.396(2) . ? C20 C21 1.404(3) . ? C21 C22 1.410(3) . ? C21 C26 1.487(2) . ? C22 N4 1.393(2) . ? C22 C23 1.426(3) . ? C23 C24 1.378(3) . ? C24 C25 1.407(3) . ? C25 N4 1.346(3) . ? C26 C27 1.396(3) . ? C26 C31 1.400(3) . ? C27 C28 1.395(3) . ? C28 C29 1.391(3) . ? C29 C30 1.395(3) . ? C29 S2 1.766(2) . ? C30 C31 1.379(3) . ? C32 S2 1.793(2) . ? Cu1 N4 1.9544(16) . ? Cu1 N1 1.9549(16) . ? Cu1 N2 1.9566(16) . ? Cu1 N3 1.9654(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 111.78(17) . . ? C3 C2 C1 106.09(17) . . ? C2 C3 C4 107.33(17) . . ? N1 C4 C5 124.11(17) . . ? N1 C4 C3 108.43(17) . . ? C5 C4 C3 127.45(18) . . ? C6 C5 C4 124.56(18) . . ? C6 C5 C10 117.31(17) . . ? C4 C5 C10 118.09(17) . . ? N2 C6 C5 123.92(18) . . ? N2 C6 C7 108.75(16) . . ? C5 C6 C7 127.28(18) . . ? C8 C7 C6 107.12(17) . . ? C7 C8 C9 106.10(18) . . ? N2 C9 C8 111.58(17) . . ? C11 C10 C15 118.26(18) . . ? C11 C10 C5 119.91(18) . . ? C15 C10 C5 121.82(17) . . ? C12 C11 C10 121.18(19) . . ? C13 C12 C11 120.10(18) . . ? C12 C13 C14 119.37(18) . . ? C12 C13 S1 123.17(15) . . ? C14 C13 S1 117.44(15) . . ? C15 C14 C13 120.21(18) . . ? C14 C15 C10 120.85(18) . . ? N3 C17 C18 111.96(17) . . ? C19 C18 C17 105.88(18) . . ? C18 C19 C20 107.40(17) . . ? N3 C20 C21 124.11(18) . . ? N3 C20 C19 108.51(16) . . ? C21 C20 C19 127.37(18) . . ? C20 C21 C22 125.11(17) . . ? C20 C21 C26 118.54(17) . . ? C22 C21 C26 116.34(17) . . ? N4 C22 C21 123.67(17) . . ? N4 C22 C23 108.59(17) . . ? C21 C22 C23 127.61(18) . . ? C24 C23 C22 107.20(17) . . ? C23 C24 C25 106.20(18) . . ? N4 C25 C24 111.62(17) . . ? C27 C26 C31 118.03(18) . . ? C27 C26 C21 122.35(17) . . ? C31 C26 C21 119.57(17) . . ? C28 C27 C26 120.82(18) . . ? C29 C28 C27 120.19(19) . . ? C28 C29 C30 119.28(18) . . ? C28 C29 S2 124.34(16) . . ? C30 C29 S2 116.35(15) . . ? C31 C30 C29 120.19(18) . . ? C30 C31 C26 121.36(19) . . ? N4 Cu1 N1 149.46(7) . . ? N4 Cu1 N2 95.22(7) . . ? N1 Cu1 N2 91.70(7) . . ? N4 Cu1 N3 91.77(7) . . ? N1 Cu1 N3 97.36(7) . . ? N2 Cu1 N3 149.16(7) . . ? C1 N1 C4 106.35(16) . . ? C1 N1 Cu1 125.74(13) . . ? C4 N1 Cu1 127.05(13) . . ? C9 N2 C6 106.45(16) . . ? C9 N2 Cu1 124.86(13) . . ? C6 N2 Cu1 127.62(13) . . ? C17 N3 C20 106.25(16) . . ? C17 N3 Cu1 126.20(13) . . ? C20 N3 Cu1 127.18(13) . . ? C25 N4 C22 106.39(16) . . ? C25 N4 Cu1 124.94(13) . . ? C22 N4 Cu1 127.85(13) . . ? C13 S1 C16 102.87(10) . . ? C29 S2 C32 103.36(10) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.510 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.078 data_[Cu(4-mtdpm)(hfacac)] _database_code_depnum_ccdc_archive 'CCDC 246587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cl2 Cu F6 N2 O2 S' _chemical_formula_weight 620.87 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6561(8) _cell_length_b 16.1930(15) _cell_length_c 33.492(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4694.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.40 _cell_measurement_theta_max 27.52 _exptl_crystal_description rod _exptl_crystal_colour red-green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2488 _exptl_absorpt_coefficient_mu 1.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.668905 _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 15746 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.52 _reflns_number_total 9942 _reflns_number_gt 9206 _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^)+(0.0697P)^2^+0.3795P] 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 0.603(11) _refine_ls_number_reflns 9942 _refine_ls_number_parameters 652 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 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 0.1315(5) 0.9757(2) 0.08470(12) 0.0175(8) Uani 1 1 d . . . H1 H 0.0802 1.0046 0.1055 0.021 Uiso 1 1 calc R . . C2 C 0.1176(5) 0.9954(2) 0.04405(12) 0.0210(9) Uani 1 1 d . . . H2 H 0.0575 1.0386 0.0328 0.025 Uiso 1 1 calc R . . C3 C 0.2087(5) 0.9394(2) 0.02356(12) 0.0181(8) Uani 1 1 d . . . H3 H 0.2230 0.9367 -0.0045 0.022 Uiso 1 1 calc R . . C4 C 0.2769(5) 0.8869(2) 0.05257(12) 0.0159(8) Uani 1 1 d . . . C5 C 0.3784(4) 0.8205(2) 0.04602(12) 0.0155(8) Uani 1 1 d . . . C6 C 0.4379(5) 0.7685(2) 0.07595(12) 0.0152(8) Uani 1 1 d . . . C7 C 0.5534(5) 0.7063(2) 0.07105(12) 0.0175(8) Uani 1 1 d . . . H7 H 0.6006 0.6898 0.0467 0.021 Uiso 1 1 calc R . . C8 C 0.5832(5) 0.6748(2) 0.10858(12) 0.0200(8) Uani 1 1 d . . . H8 H 0.6545 0.6322 0.1150 0.024 Uiso 1 1 calc R . . C9 C 0.4872(5) 0.7182(2) 0.13583(12) 0.0179(8) Uani 1 1 d . . . H9 H 0.4837 0.7086 0.1638 0.021 Uiso 1 1 calc R . . C10 C 0.4229(4) 0.8038(2) 0.00419(11) 0.0146(8) Uani 1 1 d . . . C11 C 0.4976(5) 0.8635(2) -0.01915(12) 0.0184(8) Uani 1 1 d . . . H11 H 0.5266 0.9146 -0.0073 0.022 Uiso 1 1 calc R . . C12 C 0.5298(4) 0.8498(2) -0.05882(12) 0.0189(8) Uani 1 1 d . . . H12 H 0.5788 0.8917 -0.0741 0.023 Uiso 1 1 calc R . . C13 C 0.4910(5) 0.7750(2) -0.07678(12) 0.0165(8) Uani 1 1 d . . . C14 C 0.4239(5) 0.7127(2) -0.05301(12) 0.0175(8) Uani 1 1 d . . . H14 H 0.4015 0.6604 -0.0644 0.021 Uiso 1 1 calc R . . C15 C 0.3903(5) 0.7270(2) -0.01343(12) 0.0174(8) Uani 1 1 d . . . H15 H 0.3445 0.6845 0.0021 0.021 Uiso 1 1 calc R . . C16 C 0.5889(6) 0.8477(2) -0.14820(13) 0.0296(10) Uani 1 1 d . . . H16A H 0.5239 0.8947 -0.1407 0.044 Uiso 1 1 calc R . . H16B H 0.5941 0.8436 -0.1774 0.044 Uiso 1 1 calc R . . H16C H 0.6931 0.8555 -0.1374 0.044 Uiso 1 1 calc R . . C17 C 0.0216(5) 1.0230(2) 0.21570(13) 0.0222(9) Uani 1 1 d . . . C18 C 0.1200(5) 0.9466(2) 0.20492(12) 0.0183(8) Uani 1 1 d . . . C19 C 0.1828(5) 0.9020(2) 0.23579(13) 0.0212(9) Uani 1 1 d . . . H19 H 0.1736 0.9204 0.2626 0.025 Uiso 1 1 calc R . . C20 C 0.2609(5) 0.8286(2) 0.22664(12) 0.0175(8) Uani 1 1 d . . . C21 C 0.3139(5) 0.7750(3) 0.26255(14) 0.0250(9) Uani 1 1 d . . . C22 C 0.8337(5) 0.0221(2) 0.91559(12) 0.0199(8) Uani 1 1 d . . . H22 H 0.8852 -0.0070 0.8949 0.024 Uiso 1 1 calc R . . C23 C 0.8477(5) 0.0034(2) 0.95626(11) 0.0180(8) Uani 1 1 d . . . H23 H 0.9069 -0.0399 0.9677 0.022 Uiso 1 1 calc R . . C24 C 0.7577(5) 0.0609(2) 0.97655(12) 0.0164(8) Uani 1 1 d . . . H24 H 0.7450 0.0652 1.0047 0.020 Uiso 1 1 calc R . . C25 C 0.6877(4) 0.1124(2) 0.94675(11) 0.0131(7) Uani 1 1 d . . . C26 C 0.5879(4) 0.1784(2) 0.95337(12) 0.0148(8) Uani 1 1 d . . . C27 C 0.5262(4) 0.2294(2) 0.92309(12) 0.0145(8) Uani 1 1 d . . . C28 C 0.4112(5) 0.2921(2) 0.92743(13) 0.0194(8) Uani 1 1 d . . . H28 H 0.3647 0.3096 0.9517 0.023 Uiso 1 1 calc R . . C29 C 0.3803(5) 0.3223(2) 0.88989(12) 0.0203(8) Uani 1 1 d . . . H29 H 0.3088 0.3646 0.8831 0.024 Uiso 1 1 calc R . . C30 C 0.4760(5) 0.2780(2) 0.86350(13) 0.0185(8) Uani 1 1 d . . . H30 H 0.4785 0.2861 0.8354 0.022 Uiso 1 1 calc R . . C31 C 0.5410(4) 0.1963(2) 0.99496(12) 0.0157(8) Uani 1 1 d . . . C32 C 0.4694(4) 0.1367(2) 1.01885(11) 0.0157(7) Uani 1 1 d . . . H32 H 0.4432 0.0849 1.0074 0.019 Uiso 1 1 calc R . . C33 C 0.4357(4) 0.1507(2) 1.05856(12) 0.0191(8) Uani 1 1 d . . . H33 H 0.3859 0.1093 1.0740 0.023 Uiso 1 1 calc R . . C34 C 0.4757(5) 0.2269(2) 1.07606(12) 0.0164(8) Uani 1 1 d . . . C35 C 0.5409(5) 0.2877(2) 1.05193(12) 0.0179(8) Uani 1 1 d . . . H35 H 0.5632 0.3403 1.0631 0.022 Uiso 1 1 calc R . . C36 C 0.5734(5) 0.2735(2) 1.01273(12) 0.0167(8) Uani 1 1 d . . . H36 H 0.6186 0.3161 0.9971 0.020 Uiso 1 1 calc R . . C37 C 0.3840(6) 0.1546(2) 1.14826(13) 0.0365(12) Uani 1 1 d . . . H37A H 0.2826 0.1428 1.1366 0.055 Uiso 1 1 calc R . . H37B H 0.3736 0.1606 1.1773 0.055 Uiso 1 1 calc R . . H37C H 0.4548 0.1090 1.1423 0.055 Uiso 1 1 calc R . . C38 C 0.9458(5) -0.0278(2) 0.78477(13) 0.0234(9) Uani 1 1 d . . . C39 C 0.8546(5) 0.0513(2) 0.79522(12) 0.0178(8) Uani 1 1 d . . . C40 C 0.8166(5) 0.1053(2) 0.76483(12) 0.0204(8) Uani 1 1 d . . . H40 H 0.8459 0.0930 0.7382 0.024 Uiso 1 1 calc R . . C41 C 0.7357(5) 0.1778(2) 0.77294(12) 0.0163(8) Uani 1 1 d . . . C42 C 0.7028(5) 0.2372(2) 0.73836(13) 0.0212(8) Uani 1 1 d . . . C43 C 0.6917(5) 0.9131(2) 0.12450(12) 0.0224(9) Uani 1 1 d . . . H43A H 0.6700 0.8544 0.1186 0.027 Uiso 1 1 calc R . . H43B H 0.7985 0.9171 0.1349 0.027 Uiso 1 1 calc R . . C44 C 0.2682(5) 0.0849(2) 0.87742(13) 0.0242(9) Uani 1 1 d . . . H44A H 0.2888 0.1441 0.8826 0.029 Uiso 1 1 calc R . . H44B H 0.1609 0.0797 0.8675 0.029 Uiso 1 1 calc R . . Cl1 Cl 0.67600(14) 0.97207(6) 0.07996(3) 0.0308(2) Uani 1 1 d . . . Cl2 Cl 0.56076(13) 0.94914(6) 0.16098(3) 0.0263(2) Uani 1 1 d . . . Cl3 Cl 0.39908(14) 0.04770(6) 0.84059(3) 0.0282(2) Uani 1 1 d . . . Cl4 Cl 0.28888(14) 0.02812(6) 0.92216(3) 0.0302(2) Uani 1 1 d . . . Cu1 Cu 0.25469(5) 0.85076(2) 0.140234(14) 0.01660(11) Uani 1 1 d . . . Cu2 Cu 0.70856(5) 0.14549(3) 0.859233(14) 0.01669(11) Uani 1 1 d . . . F1 F 0.0019(4) 1.03431(17) 0.25448(7) 0.0364(7) Uani 1 1 d . . . F2 F -0.1189(3) 1.01720(16) 0.19939(9) 0.0388(7) Uani 1 1 d . . . F3 F 0.0866(4) 1.09100(13) 0.20076(8) 0.0381(7) Uani 1 1 d . . . F4 F 0.2144(3) 0.71501(18) 0.26982(10) 0.0453(8) Uani 1 1 d . . . F5 F 0.3315(4) 0.81959(18) 0.29581(8) 0.0473(9) Uani 1 1 d . . . F6 F 0.4503(3) 0.73942(14) 0.25547(7) 0.0250(5) Uani 1 1 d . . . F7 F 0.8549(4) -0.09311(14) 0.79054(9) 0.0406(7) Uani 1 1 d . . . F8 F 0.9924(4) -0.03015(18) 0.74730(7) 0.0398(8) Uani 1 1 d . . . F9 F 1.0670(4) -0.03633(16) 0.80824(9) 0.0427(7) Uani 1 1 d . . . F10 F 0.7670(4) 0.21322(16) 0.70442(8) 0.0425(8) Uani 1 1 d . . . F11 F 0.7600(3) 0.31231(14) 0.74579(8) 0.0340(7) Uani 1 1 d . . . F12 F 0.5527(3) 0.24759(19) 0.73307(9) 0.0429(8) Uani 1 1 d . . . N1 N 0.2262(4) 0.91103(17) 0.09053(10) 0.0161(7) Uani 1 1 d . . . N2 N 0.4018(4) 0.77466(18) 0.11635(10) 0.0165(7) Uani 1 1 d . . . N3 N 0.7382(4) 0.08648(17) 0.90941(10) 0.0161(7) Uani 1 1 d . . . N4 N 0.5640(4) 0.22244(18) 0.88335(10) 0.0166(7) Uani 1 1 d . . . O1 O 0.1276(4) 0.93497(16) 0.16806(8) 0.0241(7) Uani 1 1 d . . . O2 O 0.2913(3) 0.79832(15) 0.19341(8) 0.0195(6) Uani 1 1 d . . . O3 O 0.8255(4) 0.05745(16) 0.83170(8) 0.0247(7) Uani 1 1 d . . . O4 O 0.6853(3) 0.20161(15) 0.80628(8) 0.0191(6) Uani 1 1 d . . . S1 S 0.50739(12) 0.75435(6) -0.12821(3) 0.0197(2) Uani 1 1 d . . . S2 S 0.45913(12) 0.24862(6) 1.12747(3) 0.0213(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.0122(16) 0.018(2) 0.0010(14) 0.0026(16) 0.0032(14) C2 0.027(2) 0.0108(16) 0.025(2) 0.0014(14) -0.0010(17) 0.0006(15) C3 0.022(2) 0.0164(16) 0.015(2) 0.0030(14) 0.0012(15) -0.0005(14) C4 0.020(2) 0.0120(15) 0.016(2) 0.0011(13) -0.0014(15) -0.0033(14) C5 0.0142(19) 0.0144(16) 0.018(2) -0.0004(14) -0.0009(15) -0.0029(14) C6 0.0183(19) 0.0119(15) 0.015(2) -0.0001(13) 0.0022(15) -0.0009(13) C7 0.019(2) 0.0137(16) 0.020(2) -0.0025(14) 0.0007(16) 0.0008(14) C8 0.024(2) 0.0161(17) 0.020(2) 0.0018(14) 0.0004(16) 0.0035(15) C9 0.022(2) 0.0157(16) 0.016(2) 0.0040(14) -0.0014(16) 0.0017(14) C10 0.0166(19) 0.0159(17) 0.011(2) 0.0001(14) -0.0003(14) 0.0002(14) C11 0.020(2) 0.0145(16) 0.021(2) -0.0035(15) 0.0030(15) -0.0022(14) C12 0.021(2) 0.0155(17) 0.020(2) 0.0033(15) 0.0024(15) -0.0018(15) C13 0.019(2) 0.0205(18) 0.010(2) 0.0011(14) -0.0020(15) 0.0040(14) C14 0.019(2) 0.0130(16) 0.020(2) 0.0010(14) -0.0020(16) -0.0010(14) C15 0.023(2) 0.0132(16) 0.016(2) 0.0045(13) 0.0029(16) -0.0003(14) C16 0.049(3) 0.0227(19) 0.017(2) 0.0029(17) 0.0062(19) 0.007(2) C17 0.031(2) 0.0138(17) 0.022(2) 0.0014(15) 0.0073(18) 0.0027(15) C18 0.023(2) 0.0103(16) 0.022(2) -0.0005(14) 0.0009(16) -0.0013(14) C19 0.032(2) 0.0199(17) 0.012(2) -0.0008(15) -0.0011(17) 0.0025(16) C20 0.022(2) 0.0181(16) 0.012(2) 0.0021(14) 0.0013(15) -0.0013(14) C21 0.024(2) 0.031(2) 0.019(2) 0.0010(17) 0.0002(17) 0.0036(17) C22 0.022(2) 0.0124(16) 0.025(2) -0.0006(15) 0.0009(17) 0.0011(14) C23 0.025(2) 0.0164(17) 0.013(2) 0.0044(14) -0.0009(16) -0.0001(15) C24 0.023(2) 0.0146(16) 0.012(2) 0.0000(14) -0.0011(15) 0.0008(14) C25 0.0174(19) 0.0133(15) 0.009(2) 0.0017(13) -0.0003(14) -0.0005(13) C26 0.0154(19) 0.0130(16) 0.016(2) 0.0001(13) -0.0011(15) -0.0041(13) C27 0.0170(19) 0.0141(16) 0.012(2) -0.0013(13) 0.0012(14) -0.0020(14) C28 0.020(2) 0.0147(16) 0.023(2) -0.0026(15) 0.0007(16) 0.0013(14) C29 0.018(2) 0.0171(17) 0.025(2) -0.0009(15) -0.0006(16) 0.0037(15) C30 0.024(2) 0.0149(16) 0.017(2) 0.0041(15) -0.0046(16) 0.0020(14) C31 0.0168(19) 0.0135(16) 0.017(2) 0.0019(14) 0.0000(15) 0.0006(14) C32 0.0200(19) 0.0131(16) 0.014(2) 0.0024(14) 0.0017(14) -0.0003(14) C33 0.020(2) 0.0153(17) 0.022(2) 0.0040(15) 0.0033(15) -0.0010(15) C34 0.019(2) 0.0188(17) 0.011(2) -0.0006(14) -0.0043(15) 0.0040(14) C35 0.020(2) 0.0137(16) 0.020(2) -0.0018(14) -0.0008(16) 0.0013(14) C36 0.023(2) 0.0110(16) 0.016(2) 0.0003(13) -0.0016(16) -0.0014(14) C37 0.067(3) 0.0201(19) 0.022(3) 0.0101(17) 0.017(2) 0.016(2) C38 0.035(2) 0.0151(17) 0.020(2) -0.0006(15) 0.0057(18) 0.0022(16) C39 0.024(2) 0.0125(16) 0.017(2) -0.0023(14) 0.0029(16) -0.0019(14) C40 0.028(2) 0.0195(17) 0.013(2) -0.0022(15) 0.0039(17) 0.0026(16) C41 0.0171(19) 0.0162(16) 0.016(2) 0.0009(14) -0.0012(15) -0.0030(14) C42 0.025(2) 0.0226(18) 0.016(2) -0.0004(16) -0.0011(16) 0.0012(16) C43 0.028(2) 0.0180(17) 0.021(2) 0.0030(15) -0.0040(17) 0.0028(16) C44 0.031(2) 0.0189(17) 0.023(2) 0.0026(15) -0.0016(18) 0.0038(16) Cl1 0.0416(7) 0.0244(5) 0.0263(6) 0.0069(4) -0.0009(5) -0.0016(4) Cl2 0.0348(6) 0.0215(4) 0.0224(6) -0.0031(4) -0.0039(4) 0.0055(4) Cl3 0.0376(6) 0.0239(5) 0.0230(6) -0.0028(4) -0.0033(4) 0.0077(4) Cl4 0.0408(7) 0.0240(5) 0.0259(6) 0.0078(4) -0.0029(5) -0.0033(4) Cu1 0.0245(3) 0.0135(2) 0.0117(3) 0.00061(17) 0.00038(18) 0.00341(17) Cu2 0.0250(3) 0.01307(19) 0.0120(3) 0.00131(17) 0.00162(18) 0.00359(17) F1 0.063(2) 0.0251(14) 0.0214(16) -0.0050(10) 0.0059(13) 0.0148(12) F2 0.0310(16) 0.0368(14) 0.0485(19) -0.0150(12) -0.0071(13) 0.0104(12) F3 0.060(2) 0.0125(11) 0.0414(18) 0.0053(10) 0.0138(14) 0.0013(11) F4 0.0305(16) 0.0540(17) 0.051(2) 0.0382(15) 0.0025(14) -0.0023(13) F5 0.080(2) 0.0477(16) 0.0138(15) -0.0073(12) -0.0124(15) 0.0355(16) F6 0.0265(13) 0.0205(11) 0.0280(15) 0.0013(9) -0.0060(10) 0.0045(10) F7 0.057(2) 0.0118(11) 0.0531(19) -0.0027(11) 0.0181(16) -0.0020(11) F8 0.071(2) 0.0270(15) 0.0216(17) 0.0051(10) 0.0203(14) 0.0220(13) F9 0.0488(19) 0.0373(14) 0.0422(19) -0.0114(12) -0.0134(15) 0.0209(13) F10 0.081(2) 0.0292(13) 0.0178(16) 0.0069(10) 0.0104(14) 0.0208(14) F11 0.0449(17) 0.0171(11) 0.0400(18) 0.0111(10) -0.0078(13) -0.0012(11) F12 0.0254(15) 0.0616(19) 0.0416(19) 0.0290(15) -0.0060(13) -0.0048(14) N1 0.0200(18) 0.0118(13) 0.0165(19) 0.0013(11) 0.0008(13) 0.0004(12) N2 0.0226(18) 0.0125(13) 0.0144(18) 0.0037(11) 0.0042(13) -0.0002(12) N3 0.0194(17) 0.0128(13) 0.0160(19) -0.0006(11) 0.0020(13) 0.0018(12) N4 0.0174(17) 0.0148(14) 0.0176(19) 0.0012(12) 0.0005(13) 0.0013(12) O1 0.0425(19) 0.0185(13) 0.0115(16) 0.0007(10) 0.0008(13) 0.0078(12) O2 0.0254(16) 0.0181(12) 0.0149(16) -0.0005(10) 0.0009(12) 0.0021(11) O3 0.0385(18) 0.0193(13) 0.0163(17) 0.0017(11) 0.0027(13) 0.0091(12) O4 0.0268(16) 0.0191(13) 0.0114(15) 0.0019(10) 0.0008(11) 0.0033(11) S1 0.0234(5) 0.0214(4) 0.0144(5) 0.0002(4) 0.0006(4) 0.0029(4) S2 0.0254(5) 0.0256(5) 0.0128(5) -0.0010(4) 0.0005(4) 0.0050(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(4) . ? C1 C2 1.403(6) . ? C2 C3 1.383(5) . ? C3 C4 1.420(5) . ? C4 N1 1.401(5) . ? C4 C5 1.405(5) . ? C5 C6 1.407(5) . ? C5 C10 1.478(5) . ? C6 N2 1.392(5) . ? C6 C7 1.429(5) . ? C7 C8 1.381(5) . ? C8 C9 1.420(5) . ? C9 N2 1.345(5) . ? C10 C11 1.401(5) . ? C10 C15 1.405(5) . ? C11 C12 1.376(5) . ? C12 C13 1.394(5) . ? C13 C14 1.410(5) . ? C13 S1 1.760(4) . ? C14 C15 1.377(5) . ? C16 S1 1.797(4) . ? C17 F1 1.323(5) . ? C17 F3 1.334(4) . ? C17 F2 1.337(5) . ? C17 C18 1.545(5) . ? C18 O1 1.251(5) . ? C18 C19 1.374(5) . ? C19 C20 1.402(5) . ? C20 O2 1.244(5) . ? C20 C21 1.552(6) . ? C21 F4 1.321(5) . ? C21 F6 1.335(5) . ? C21 F5 1.336(5) . ? C22 N3 1.346(5) . ? C22 C23 1.401(5) . ? C23 C24 1.390(5) . ? C24 C25 1.435(5) . ? C25 N3 1.389(5) . ? C25 C26 1.392(5) . ? C26 C27 1.413(5) . ? C26 C31 1.480(5) . ? C27 N4 1.375(5) . ? C27 C28 1.429(5) . ? C28 C29 1.376(6) . ? C29 C30 1.408(5) . ? C30 N4 1.354(5) . ? C31 C32 1.399(5) . ? C31 C36 1.413(5) . ? C32 C33 1.381(5) . ? C33 C34 1.410(5) . ? C34 C35 1.392(5) . ? C34 S2 1.763(4) . ? C35 C36 1.362(5) . ? C37 S2 1.796(4) . ? C38 F9 1.318(5) . ? C38 F8 1.319(5) . ? C38 F7 1.332(5) . ? C38 C39 1.544(5) . ? C39 O3 1.251(5) . ? C39 C40 1.383(5) . ? C40 C41 1.393(5) . ? C41 O4 1.259(5) . ? C41 C42 1.532(6) . ? C42 F12 1.322(5) . ? C42 F10 1.324(5) . ? C42 F11 1.336(5) . ? C43 Cl2 1.766(4) . ? C43 Cl1 1.776(4) . ? C44 Cl4 1.767(4) . ? C44 Cl3 1.780(5) . ? Cu1 N2 1.944(3) . ? Cu1 N1 1.946(3) . ? Cu1 O1 1.985(3) . ? Cu1 O2 1.998(3) . ? Cu1 S1 2.7644(11) 4_465 ? Cu2 N4 1.942(3) . ? Cu2 N3 1.950(3) . ? Cu2 O3 1.977(3) . ? Cu2 O4 2.003(3) . ? Cu2 S2 2.8005(11) 4_557 ? S1 Cu1 2.7644(11) 4_565 ? S2 Cu2 2.8005(11) 4_457 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 111.7(3) . . ? C3 C2 C1 106.5(3) . . ? C2 C3 C4 106.9(4) . . ? N1 C4 C5 123.4(3) . . ? N1 C4 C3 108.9(3) . . ? C5 C4 C3 127.7(4) . . ? C4 C5 C6 125.1(4) . . ? C4 C5 C10 116.8(3) . . ? C6 C5 C10 118.1(3) . . ? N2 C6 C5 124.6(3) . . ? N2 C6 C7 108.6(3) . . ? C5 C6 C7 126.6(4) . . ? C8 C7 C6 106.6(3) . . ? C7 C8 C9 107.0(3) . . ? N2 C9 C8 110.3(4) . . ? C11 C10 C15 118.0(4) . . ? C11 C10 C5 121.5(3) . . ? C15 C10 C5 120.5(3) . . ? C12 C11 C10 121.4(3) . . ? C11 C12 C13 120.6(4) . . ? C12 C13 C14 118.5(4) . . ? C12 C13 S1 124.6(3) . . ? C14 C13 S1 116.7(3) . . ? C15 C14 C13 120.7(3) . . ? C14 C15 C10 120.7(3) . . ? F1 C17 F3 108.0(3) . . ? F1 C17 F2 107.1(3) . . ? F3 C17 F2 106.8(4) . . ? F1 C17 C18 114.3(3) . . ? F3 C17 C18 109.9(3) . . ? F2 C17 C18 110.4(3) . . ? O1 C18 C19 130.0(4) . . ? O1 C18 C17 112.4(3) . . ? C19 C18 C17 117.6(4) . . ? C18 C19 C20 118.2(4) . . ? O2 C20 C19 129.2(4) . . ? O2 C20 C21 114.3(3) . . ? C19 C20 C21 116.5(4) . . ? F4 C21 F6 107.0(3) . . ? F4 C21 F5 108.6(4) . . ? F6 C21 F5 106.3(4) . . ? F4 C21 C20 111.2(4) . . ? F6 C21 C20 111.4(4) . . ? F5 C21 C20 112.2(3) . . ? N3 C22 C23 111.7(4) . . ? C24 C23 C22 106.4(3) . . ? C23 C24 C25 106.6(3) . . ? N3 C25 C26 124.8(3) . . ? N3 C25 C24 108.5(3) . . ? C26 C25 C24 126.7(4) . . ? C25 C26 C27 124.7(4) . . ? C25 C26 C31 118.1(3) . . ? C27 C26 C31 117.2(3) . . ? N4 C27 C26 123.8(3) . . ? N4 C27 C28 108.8(3) . . ? C26 C27 C28 127.3(4) . . ? C29 C28 C27 107.2(4) . . ? C28 C29 C30 106.1(3) . . ? N4 C30 C29 111.2(4) . . ? C32 C31 C36 117.3(4) . . ? C32 C31 C26 121.6(3) . . ? C36 C31 C26 121.0(3) . . ? C33 C32 C31 122.1(3) . . ? C32 C33 C34 119.5(4) . . ? C35 C34 C33 118.5(4) . . ? C35 C34 S2 117.3(3) . . ? C33 C34 S2 124.1(3) . . ? C36 C35 C34 121.6(3) . . ? C35 C36 C31 120.9(4) . . ? F9 C38 F8 108.7(4) . . ? F9 C38 F7 107.5(3) . . ? F8 C38 F7 107.2(3) . . ? F9 C38 C39 111.0(3) . . ? F8 C38 C39 113.3(3) . . ? F7 C38 C39 108.9(4) . . ? O3 C39 C40 128.3(4) . . ? O3 C39 C38 113.0(3) . . ? C40 C39 C38 118.7(4) . . ? C39 C40 C41 120.7(4) . . ? O4 C41 C40 127.2(4) . . ? O4 C41 C42 114.4(3) . . ? C40 C41 C42 118.4(4) . . ? F12 C42 F10 109.5(4) . . ? F12 C42 F11 105.9(3) . . ? F10 C42 F11 105.8(3) . . ? F12 C42 C41 111.3(3) . . ? F10 C42 C41 112.8(3) . . ? F11 C42 C41 111.2(3) . . ? Cl2 C43 Cl1 110.8(2) . . ? Cl4 C44 Cl3 110.3(2) . . ? N2 Cu1 N1 92.81(13) . . ? N2 Cu1 O1 172.66(14) . . ? N1 Cu1 O1 89.24(12) . . ? N2 Cu1 O2 89.63(12) . . ? N1 Cu1 O2 174.82(12) . . ? O1 Cu1 O2 87.79(11) . . ? N2 Cu1 S1 93.28(10) . 4_465 ? N1 Cu1 S1 94.93(10) . 4_465 ? O1 Cu1 S1 93.57(10) . 4_465 ? O2 Cu1 S1 89.48(8) . 4_465 ? N4 Cu2 N3 92.34(13) . . ? N4 Cu2 O3 170.68(14) . . ? N3 Cu2 O3 88.92(12) . . ? N4 Cu2 O4 90.71(12) . . ? N3 Cu2 O4 176.94(12) . . ? O3 Cu2 O4 88.03(11) . . ? N4 Cu2 S2 92.30(10) . 4_557 ? N3 Cu2 S2 93.50(10) . 4_557 ? O3 Cu2 S2 96.84(10) . 4_557 ? O4 Cu2 S2 86.62(9) . 4_557 ? C1 N1 C4 106.1(3) . . ? C1 N1 Cu1 126.3(3) . . ? C4 N1 Cu1 126.6(2) . . ? C9 N2 C6 107.4(3) . . ? C9 N2 Cu1 126.3(3) . . ? C6 N2 Cu1 126.3(3) . . ? C22 N3 C25 106.8(3) . . ? C22 N3 Cu2 126.4(3) . . ? C25 N3 Cu2 125.9(2) . . ? C30 N4 C27 106.7(3) . . ? C30 N4 Cu2 125.8(3) . . ? C27 N4 Cu2 127.5(3) . . ? C18 O1 Cu1 126.6(3) . . ? C20 O2 Cu1 126.6(2) . . ? C39 O3 Cu2 128.0(3) . . ? C41 O4 Cu2 127.7(2) . . ? C13 S1 C16 103.68(19) . . ? C13 S1 Cu1 108.76(13) . 4_565 ? C16 S1 Cu1 99.18(15) . 4_565 ? C34 S2 C37 103.8(2) . . ? C34 S2 Cu2 109.89(13) . 4_457 ? C37 S2 Cu2 100.20(16) . 4_457 ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.397 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.120 data_[Cu(3-mtdpm)(hfacac)] _database_code_depnum_ccdc_archive 'CCDC 246588' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 Cu F6 N2 O2 S' _chemical_formula_weight 535.94 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)/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 12.8881(11) _cell_length_b 16.6327(14) _cell_length_c 19.7978(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.5230(10) _cell_angle_gamma 90.00 _cell_volume 4216.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5640 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 1.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.806529 _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 34862 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.54 _reflns_number_total 9446 _reflns_number_gt 7776 _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^)+(0.0517P)^2^+2.2473P] 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 9446 _refine_ls_number_parameters 597 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.002 _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 0.20331(2) 0.730003(14) 1.047525(12) 0.01823(7) Uani 1 1 d . . . O1 O 0.20829(12) 0.82778(9) 1.10435(7) 0.0233(3) Uani 1 1 d . . . O2 O 0.13222(12) 0.67387(8) 1.11676(7) 0.0216(3) Uani 1 1 d . . . N2 N 0.19080(13) 0.63543(10) 0.98989(8) 0.0194(4) Uani 1 1 d . . . N1 N 0.29099(14) 0.78416(10) 0.98898(8) 0.0196(4) Uani 1 1 d . . . C4 C 0.30916(17) 0.76075(13) 0.92370(10) 0.0218(4) Uani 1 1 d . . . C19 C 0.11222(17) 0.78239(13) 1.19266(11) 0.0223(4) Uani 1 1 d . . . H19 H 0.0837 0.7978 1.2329 0.027 Uiso 1 1 calc R . . C6 C 0.21730(16) 0.62953(13) 0.92343(10) 0.0201(4) Uani 1 1 d . . . C18 C 0.16216(16) 0.83876(12) 1.15605(10) 0.0199(4) Uani 1 1 d . . . C1 C 0.34311(16) 0.85268(13) 1.00281(11) 0.0230(4) Uani 1 1 d . . . H1 H 0.3437 0.8819 1.0441 0.028 Uiso 1 1 calc R . . C20 C 0.10416(16) 0.70319(13) 1.17003(10) 0.0200(4) Uani 1 1 d . . . C9 C 0.13906(17) 0.56831(13) 1.00137(11) 0.0230(4) Uani 1 1 d . . . H9 H 0.1111 0.5568 1.0427 0.028 Uiso 1 1 calc R . . C17 C 0.16171(19) 0.92715(13) 1.17765(11) 0.0262(5) Uani 1 1 d . . . Cu2 Cu 0.53938(2) 0.772460(14) 0.080177(12) 0.01937(7) Uani 1 1 d . . . O3 O 0.61884(12) 0.83522(9) 0.01865(7) 0.0254(3) Uani 1 1 d . . . N3 N 0.54302(14) 0.86346(10) 0.14109(8) 0.0206(4) Uani 1 1 d . . . O4 O 0.53693(12) 0.68187(9) 0.01696(7) 0.0244(3) Uani 1 1 d . . . N4 N 0.45278(14) 0.71055(10) 0.13511(8) 0.0191(4) Uani 1 1 d . . . C22 C 0.58966(18) 0.93378(13) 0.13284(11) 0.0254(5) Uani 1 1 d . . . H22 H 0.6192 0.9488 0.0929 0.030 Uiso 1 1 calc R . . C41 C 0.58287(16) 0.67685(13) -0.03556(10) 0.0221(4) Uani 1 1 d . . . C25 C 0.51198(16) 0.86418(12) 0.20660(10) 0.0201(4) Uani 1 1 d . . . C40 C 0.63830(17) 0.73614(13) -0.06536(11) 0.0256(5) Uani 1 1 d . . . H40 H 0.6684 0.7250 -0.1060 0.031 Uiso 1 1 calc R . . C27 C 0.43243(16) 0.72824(12) 0.20136(10) 0.0189(4) Uani 1 1 d . . . C39 C 0.64980(17) 0.81187(14) -0.03579(11) 0.0246(5) Uani 1 1 d . . . C38 C 0.70372(19) 0.87856(15) -0.07226(12) 0.0314(5) Uani 1 1 d . . . C30 C 0.40791(16) 0.63914(12) 0.11934(10) 0.0212(4) Uani 1 1 d . . . H30 H 0.4098 0.6126 0.0770 0.025 Uiso 1 1 calc R . . C42 C 0.57808(18) 0.59212(14) -0.06576(11) 0.0269(5) Uani 1 1 d . . . F12 F 0.48619(10) 0.55748(8) -0.06101(6) 0.0319(3) Uani 1 1 d . . . F2 F 0.25459(12) 0.96069(8) 1.17723(7) 0.0388(3) Uani 1 1 d . . . F3 F 0.13279(12) 0.93752(8) 1.23929(7) 0.0387(4) Uani 1 1 d . . . F11 F 0.59483(12) 0.59132(9) -0.13126(6) 0.0380(3) Uani 1 1 d . . . F9 F 0.75137(13) 0.85234(9) -0.12389(8) 0.0469(4) Uani 1 1 d . . . F8 F 0.63407(12) 0.93297(9) -0.09641(8) 0.0442(4) Uani 1 1 d . . . F10 F 0.65112(11) 0.54619(8) -0.03202(7) 0.0344(3) Uani 1 1 d . . . F7 F 0.77544(13) 0.91604(11) -0.02978(8) 0.0514(4) Uani 1 1 d . . . F5 F 0.12202(10) 0.58237(8) 1.23173(7) 0.0342(3) Uani 1 1 d . . . F6 F -0.02856(11) 0.60815(9) 1.17952(8) 0.0427(4) Uani 1 1 d . . . F4 F 0.02571(15) 0.67191(9) 1.27035(8) 0.0530(5) Uani 1 1 d . . . F1 F 0.09477(14) 0.96771(9) 1.13413(8) 0.0494(4) Uani 1 1 d . . . C28 C 0.37303(16) 0.66431(12) 0.22444(10) 0.0209(4) Uani 1 1 d . . . H28 H 0.3482 0.6606 0.2677 0.025 Uiso 1 1 calc R . . C24 C 0.54212(16) 0.93923(13) 0.23702(11) 0.0231(4) Uani 1 1 d . . . H24 H 0.5313 0.9561 0.2815 0.028 Uiso 1 1 calc R . . C11 C 0.25591(17) 0.73467(14) 0.77141(11) 0.0238(4) Uani 1 1 d . . . H11 H 0.2190 0.7804 0.7846 0.029 Uiso 1 1 calc R . . C26 C 0.46236(16) 0.80022(12) 0.23493(10) 0.0188(4) Uani 1 1 d . . . C5 C 0.27096(16) 0.68929(13) 0.89213(10) 0.0205(4) Uani 1 1 d . . . C3 C 0.37538(17) 0.81862(13) 0.89834(11) 0.0245(5) Uani 1 1 d . . . H3 H 0.4003 0.8180 0.8550 0.029 Uiso 1 1 calc R . . C7 C 0.17889(17) 0.55495(13) 0.89588(11) 0.0236(4) Uani 1 1 d . . . H7 H 0.1854 0.5354 0.8515 0.028 Uiso 1 1 calc R . . C29 C 0.35790(17) 0.60878(13) 0.17309(11) 0.0234(4) Uani 1 1 d . . . H29 H 0.3208 0.5595 0.1738 0.028 Uiso 1 1 calc R . . C10 C 0.29097(16) 0.67703(13) 0.81953(10) 0.0221(4) Uani 1 1 d . . . S1 S 0.23362(5) 0.79468(4) 0.63843(3) 0.02979(14) Uani 1 1 d . . . C32 C 0.48195(16) 0.75382(13) 0.35565(10) 0.0210(4) Uani 1 1 d . . . H32 H 0.5233 0.7105 0.3426 0.025 Uiso 1 1 calc R . . C12 C 0.27481(17) 0.72549(14) 0.70361(11) 0.0251(5) Uani 1 1 d . . . C2 C 0.39698(17) 0.87584(13) 0.94796(11) 0.0253(5) Uani 1 1 d . . . H2 H 0.4399 0.9220 0.9457 0.030 Uiso 1 1 calc R . . C8 C 0.13098(17) 0.51644(13) 0.94461(11) 0.0261(5) Uani 1 1 d . . . H8 H 0.0987 0.4650 0.9411 0.031 Uiso 1 1 calc R . . C31 C 0.43977(16) 0.80893(13) 0.30692(10) 0.0201(4) Uani 1 1 d . . . C36 C 0.37930(17) 0.87238(14) 0.32671(11) 0.0251(5) Uani 1 1 d . . . H36 H 0.3498 0.9101 0.2940 0.030 Uiso 1 1 calc R . . C23 C 0.58964(18) 0.98282(13) 0.19059(12) 0.0272(5) Uani 1 1 d . . . H23 H 0.6171 1.0357 0.1963 0.033 Uiso 1 1 calc R . . C14 C 0.36276(19) 0.60102(15) 0.73220(12) 0.0323(5) Uani 1 1 d . . . H14 H 0.3994 0.5552 0.7188 0.039 Uiso 1 1 calc R . . C13 C 0.32839(18) 0.65823(15) 0.68468(11) 0.0301(5) Uani 1 1 d . . . H13 H 0.3414 0.6517 0.6387 0.036 Uiso 1 1 calc R . . C15 C 0.34430(17) 0.60977(14) 0.79987(11) 0.0270(5) Uani 1 1 d . . . H15 H 0.3681 0.5700 0.8324 0.032 Uiso 1 1 calc R . . S2 S 0.51314(5) 0.69615(4) 0.48907(3) 0.03093(14) Uani 1 1 d . . . C33 C 0.46375(17) 0.76201(14) 0.42332(11) 0.0248(5) Uani 1 1 d . . . C21 C 0.05515(17) 0.64102(13) 1.21366(11) 0.0246(5) Uani 1 1 d . . . C35 C 0.36233(18) 0.88027(15) 0.39435(12) 0.0297(5) Uani 1 1 d . . . H35 H 0.3214 0.9237 0.4077 0.036 Uiso 1 1 calc R . . C16 C 0.1839(2) 0.87851(14) 0.68172(12) 0.0365(6) Uani 1 1 d . . . H16A H 0.1265 0.8605 0.7065 0.055 Uiso 1 1 calc R . . H16B H 0.1583 0.9197 0.6485 0.055 Uiso 1 1 calc R . . H16C H 0.2397 0.9012 0.7138 0.055 Uiso 1 1 calc R . . C34 C 0.40403(18) 0.82591(15) 0.44230(11) 0.0293(5) Uani 1 1 d . . . H34 H 0.3920 0.8321 0.4885 0.035 Uiso 1 1 calc R . . C37 C 0.5667(2) 0.61386(14) 0.44561(12) 0.0395(6) Uani 1 1 d . . . H37A H 0.5124 0.5909 0.4125 0.059 Uiso 1 1 calc R . . H37B H 0.5922 0.5725 0.4787 0.059 Uiso 1 1 calc R . . H37C H 0.6246 0.6332 0.4220 0.059 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 0.02420(14) 0.01730(13) 0.01413(13) 0.00141(9) 0.00626(10) 0.00015(10) O1 0.0327(8) 0.0220(8) 0.0166(7) 0.0001(6) 0.0084(6) -0.0038(6) O2 0.0285(8) 0.0201(7) 0.0177(7) 0.0014(6) 0.0086(6) 0.0010(6) N2 0.0239(9) 0.0195(9) 0.0153(8) 0.0022(6) 0.0043(7) 0.0033(7) N1 0.0230(9) 0.0214(9) 0.0150(8) 0.0020(7) 0.0045(7) 0.0012(7) C4 0.0226(11) 0.0269(11) 0.0166(10) 0.0036(8) 0.0050(8) 0.0036(9) C19 0.0280(11) 0.0223(10) 0.0181(10) 0.0005(8) 0.0089(9) 0.0016(9) C6 0.0213(10) 0.0234(10) 0.0154(9) 0.0001(8) 0.0014(8) 0.0067(8) C18 0.0228(10) 0.0202(10) 0.0165(9) 0.0003(8) 0.0007(8) 0.0022(8) C1 0.0246(11) 0.0236(11) 0.0211(10) 0.0021(8) 0.0042(9) 0.0014(9) C20 0.0197(10) 0.0216(10) 0.0194(10) 0.0039(8) 0.0057(8) 0.0010(8) C9 0.0272(11) 0.0206(10) 0.0218(10) 0.0024(8) 0.0047(9) 0.0020(9) C17 0.0373(13) 0.0223(11) 0.0195(10) -0.0005(8) 0.0054(9) -0.0007(10) Cu2 0.02710(15) 0.01708(13) 0.01502(13) 0.00132(9) 0.00706(10) 0.00162(10) O3 0.0324(9) 0.0238(8) 0.0216(7) 0.0039(6) 0.0099(6) 0.0020(6) N3 0.0269(9) 0.0173(8) 0.0183(8) 0.0023(7) 0.0053(7) 0.0036(7) O4 0.0333(9) 0.0252(8) 0.0160(7) -0.0002(6) 0.0082(6) 0.0011(7) N4 0.0244(9) 0.0188(8) 0.0150(8) 0.0001(6) 0.0060(7) 0.0024(7) C22 0.0312(12) 0.0183(10) 0.0274(11) 0.0019(8) 0.0069(9) 0.0005(9) C41 0.0224(11) 0.0273(11) 0.0166(10) 0.0007(8) 0.0027(8) 0.0066(9) C25 0.0227(10) 0.0194(10) 0.0182(10) -0.0001(8) 0.0024(8) 0.0064(8) C40 0.0306(12) 0.0283(11) 0.0197(10) 0.0046(9) 0.0102(9) 0.0087(10) C27 0.0203(10) 0.0224(10) 0.0147(9) 0.0006(8) 0.0042(8) 0.0037(8) C39 0.0235(11) 0.0288(12) 0.0229(11) 0.0084(9) 0.0078(9) 0.0086(9) C38 0.0308(13) 0.0319(13) 0.0339(13) 0.0091(10) 0.0139(10) 0.0061(10) C30 0.0264(11) 0.0203(10) 0.0174(10) -0.0018(8) 0.0049(8) 0.0011(8) C42 0.0293(12) 0.0329(12) 0.0194(10) -0.0028(9) 0.0065(9) 0.0011(10) F12 0.0325(7) 0.0375(8) 0.0264(7) -0.0073(6) 0.0069(6) -0.0035(6) F2 0.0523(9) 0.0282(7) 0.0384(8) -0.0054(6) 0.0150(7) -0.0168(7) F3 0.0645(10) 0.0273(7) 0.0281(7) -0.0099(6) 0.0217(7) -0.0075(7) F11 0.0509(9) 0.0446(9) 0.0215(7) -0.0110(6) 0.0171(6) -0.0037(7) F9 0.0593(10) 0.0417(9) 0.0474(9) 0.0127(7) 0.0395(8) 0.0092(8) F8 0.0428(9) 0.0364(8) 0.0577(10) 0.0279(7) 0.0239(7) 0.0131(7) F10 0.0351(8) 0.0283(7) 0.0397(8) -0.0017(6) 0.0038(6) 0.0082(6) F7 0.0444(9) 0.0598(11) 0.0515(10) 0.0088(8) 0.0112(8) -0.0215(8) F5 0.0329(7) 0.0318(7) 0.0390(8) 0.0181(6) 0.0094(6) 0.0033(6) F6 0.0312(8) 0.0461(9) 0.0494(9) 0.0197(7) -0.0019(7) -0.0140(7) F4 0.0915(13) 0.0319(8) 0.0453(9) -0.0013(7) 0.0507(9) -0.0085(8) F1 0.0734(11) 0.0262(8) 0.0440(9) -0.0021(6) -0.0130(8) 0.0186(8) C28 0.0228(10) 0.0239(11) 0.0170(10) 0.0011(8) 0.0064(8) 0.0007(8) C24 0.0248(11) 0.0210(10) 0.0232(10) -0.0049(8) 0.0015(9) 0.0038(9) C11 0.0226(11) 0.0295(12) 0.0198(10) -0.0002(8) 0.0051(8) -0.0027(9) C26 0.0183(10) 0.0216(10) 0.0167(10) -0.0004(8) 0.0021(8) 0.0063(8) C5 0.0204(10) 0.0263(11) 0.0149(9) 0.0014(8) 0.0019(8) 0.0067(8) C3 0.0243(11) 0.0306(12) 0.0197(10) 0.0058(9) 0.0071(9) 0.0017(9) C7 0.0247(11) 0.0246(11) 0.0212(10) -0.0034(8) 0.0007(8) 0.0054(9) C29 0.0273(11) 0.0211(11) 0.0225(10) 0.0007(8) 0.0066(9) -0.0025(9) C10 0.0194(10) 0.0304(11) 0.0167(10) -0.0011(8) 0.0032(8) -0.0009(9) S1 0.0341(3) 0.0365(3) 0.0184(3) 0.0049(2) 0.0014(2) -0.0110(3) C32 0.0201(10) 0.0234(10) 0.0200(10) -0.0028(8) 0.0044(8) -0.0036(8) C12 0.0223(11) 0.0346(12) 0.0181(10) 0.0001(9) 0.0013(8) -0.0073(9) C2 0.0249(11) 0.0253(11) 0.0269(11) 0.0068(9) 0.0076(9) -0.0026(9) C8 0.0276(12) 0.0228(11) 0.0274(11) -0.0025(9) 0.0015(9) 0.0003(9) C31 0.0189(10) 0.0262(11) 0.0154(9) -0.0025(8) 0.0020(8) -0.0006(8) C36 0.0205(10) 0.0286(12) 0.0264(11) -0.0065(9) 0.0035(9) 0.0017(9) C23 0.0324(12) 0.0184(10) 0.0309(12) -0.0019(9) 0.0038(10) -0.0005(9) C14 0.0308(12) 0.0391(14) 0.0282(12) -0.0076(10) 0.0083(10) 0.0031(10) C13 0.0293(12) 0.0425(14) 0.0196(11) -0.0047(10) 0.0073(9) -0.0048(11) C15 0.0266(11) 0.0320(12) 0.0225(11) -0.0022(9) 0.0030(9) 0.0026(9) S2 0.0366(3) 0.0385(3) 0.0171(3) 0.0030(2) 0.0006(2) -0.0149(3) C33 0.0235(11) 0.0328(12) 0.0186(10) -0.0026(9) 0.0039(9) -0.0110(9) C21 0.0295(12) 0.0236(11) 0.0228(11) 0.0019(8) 0.0114(9) 0.0003(9) C35 0.0241(11) 0.0362(13) 0.0301(12) -0.0156(10) 0.0087(9) -0.0015(10) C16 0.0522(16) 0.0264(12) 0.0286(12) 0.0026(10) -0.0059(11) -0.0107(11) C34 0.0261(11) 0.0414(13) 0.0214(11) -0.0114(10) 0.0079(9) -0.0102(10) C37 0.0610(18) 0.0241(12) 0.0297(13) 0.0025(10) -0.0110(12) -0.0100(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9311(17) . ? Cu1 N2 1.9392(17) . ? Cu1 O2 1.9686(14) . ? Cu1 O1 1.9744(15) . ? O1 C18 1.254(2) . ? O2 C20 1.252(2) . ? N2 C9 1.333(3) . ? N2 C6 1.400(2) . ? N1 C1 1.335(3) . ? N1 C4 1.395(3) . ? C4 C5 1.406(3) . ? C4 C3 1.416(3) . ? C19 C18 1.387(3) . ? C19 C20 1.391(3) . ? C6 C5 1.396(3) . ? C6 C7 1.421(3) . ? C18 C17 1.531(3) . ? C1 C2 1.407(3) . ? C20 C21 1.529(3) . ? C9 C8 1.411(3) . ? C17 F2 1.322(3) . ? C17 F3 1.327(2) . ? C17 F1 1.332(3) . ? Cu2 N3 1.9325(17) . ? Cu2 N4 1.9402(17) . ? Cu2 O4 1.9568(15) . ? Cu2 O3 1.9763(15) . ? O3 C39 1.253(3) . ? N3 C22 1.334(3) . ? N3 C25 1.400(3) . ? O4 C41 1.256(2) . ? N4 C30 1.342(3) . ? N4 C27 1.398(3) . ? C22 C23 1.405(3) . ? C41 C40 1.388(3) . ? C41 C42 1.529(3) . ? C25 C26 1.392(3) . ? C25 C24 1.421(3) . ? C40 C39 1.390(3) . ? C27 C26 1.402(3) . ? C27 C28 1.416(3) . ? C39 C38 1.533(3) . ? C38 F9 1.325(3) . ? C38 F8 1.325(3) . ? C38 F7 1.332(3) . ? C30 C29 1.399(3) . ? C42 F12 1.330(3) . ? C42 F10 1.332(3) . ? C42 F11 1.339(2) . ? F5 C21 1.324(3) . ? F6 C21 1.324(3) . ? F4 C21 1.328(2) . ? C28 C29 1.371(3) . ? C24 C23 1.369(3) . ? C11 C10 1.390(3) . ? C11 C12 1.399(3) . ? C26 C31 1.494(3) . ? C5 C10 1.503(3) . ? C3 C2 1.373(3) . ? C7 C8 1.363(3) . ? C10 C15 1.391(3) . ? S1 C12 1.765(2) . ? S1 C16 1.793(3) . ? C32 C33 1.393(3) . ? C32 C31 1.395(3) . ? C12 C13 1.388(3) . ? C31 C36 1.394(3) . ? C36 C35 1.387(3) . ? C14 C13 1.375(3) . ? C14 C15 1.395(3) . ? S2 C33 1.764(2) . ? S2 C37 1.796(3) . ? C33 C34 1.389(3) . ? C35 C34 1.375(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 N1 Cu1 N2 92.31(7) . . ? N1 Cu1 O2 171.69(7) . . ? N2 Cu1 O2 90.62(7) . . ? N1 Cu1 O1 88.54(7) . . ? N2 Cu1 O1 176.94(7) . . ? O2 Cu1 O1 88.93(6) . . ? C18 O1 Cu1 126.68(14) . . ? C20 O2 Cu1 127.14(14) . . ? C9 N2 C6 106.36(17) . . ? C9 N2 Cu1 126.07(14) . . ? C6 N2 Cu1 126.66(14) . . ? C1 N1 C4 107.14(18) . . ? C1 N1 Cu1 126.16(14) . . ? C4 N1 Cu1 126.68(15) . . ? N1 C4 C5 124.11(19) . . ? N1 C4 C3 108.08(19) . . ? C5 C4 C3 127.7(2) . . ? C18 C19 C20 119.58(19) . . ? C5 C6 N2 123.61(19) . . ? C5 C6 C7 128.31(19) . . ? N2 C6 C7 108.08(18) . . ? O1 C18 C19 128.25(19) . . ? O1 C18 C17 112.65(18) . . ? C19 C18 C17 119.09(18) . . ? N1 C1 C2 110.86(19) . . ? O2 C20 C19 128.44(19) . . ? O2 C20 C21 112.95(18) . . ? C19 C20 C21 118.61(18) . . ? N2 C9 C8 111.68(19) . . ? F2 C17 F3 107.46(18) . . ? F2 C17 F1 107.62(19) . . ? F3 C17 F1 107.47(19) . . ? F2 C17 C18 111.80(19) . . ? F3 C17 C18 113.08(18) . . ? F1 C17 C18 109.18(17) . . ? N3 Cu2 N4 92.33(7) . . ? N3 Cu2 O4 178.70(7) . . ? N4 Cu2 O4 88.93(7) . . ? N3 Cu2 O3 89.62(7) . . ? N4 Cu2 O3 175.69(7) . . ? O4 Cu2 O3 89.10(6) . . ? C39 O3 Cu2 127.19(15) . . ? C22 N3 C25 106.62(17) . . ? C22 N3 Cu2 126.15(15) . . ? C25 N3 Cu2 126.56(14) . . ? C41 O4 Cu2 127.28(15) . . ? C30 N4 C27 106.42(17) . . ? C30 N4 Cu2 126.83(14) . . ? C27 N4 Cu2 126.54(14) . . ? N3 C22 C23 111.59(19) . . ? O4 C41 C40 128.2(2) . . ? O4 C41 C42 112.52(19) . . ? C40 C41 C42 119.24(18) . . ? C26 C25 N3 124.02(18) . . ? C26 C25 C24 128.08(19) . . ? N3 C25 C24 107.89(18) . . ? C41 C40 C39 120.0(2) . . ? N4 C27 C26 123.62(18) . . ? N4 C27 C28 108.10(17) . . ? C26 C27 C28 128.18(19) . . ? O3 C39 C40 127.9(2) . . ? O3 C39 C38 112.8(2) . . ? C40 C39 C38 119.33(19) . . ? F9 C38 F8 107.51(19) . . ? F9 C38 F7 107.0(2) . . ? F8 C38 F7 107.5(2) . . ? F9 C38 C39 113.6(2) . . ? F8 C38 C39 109.85(19) . . ? F7 C38 C39 111.13(19) . . ? N4 C30 C29 111.48(18) . . ? F12 C42 F10 107.48(19) . . ? F12 C42 F11 107.88(18) . . ? F10 C42 F11 107.32(18) . . ? F12 C42 C41 111.61(18) . . ? F10 C42 C41 109.74(17) . . ? F11 C42 C41 112.59(19) . . ? C29 C28 C27 107.66(18) . . ? C23 C24 C25 107.59(19) . . ? C10 C11 C12 120.2(2) . . ? C25 C26 C27 125.17(19) . . ? C25 C26 C31 117.30(18) . . ? C27 C26 C31 117.52(18) . . ? C6 C5 C4 124.83(19) . . ? C6 C5 C10 118.39(19) . . ? C4 C5 C10 116.78(19) . . ? C2 C3 C4 107.39(19) . . ? C8 C7 C6 107.74(19) . . ? C28 C29 C30 106.35(19) . . ? C11 C10 C15 119.68(19) . . ? C11 C10 C5 118.95(19) . . ? C15 C10 C5 121.37(19) . . ? C12 S1 C16 104.57(11) . . ? C33 C32 C31 120.4(2) . . ? C13 C12 C11 119.5(2) . . ? C13 C12 S1 116.45(17) . . ? C11 C12 S1 124.02(18) . . ? C3 C2 C1 106.5(2) . . ? C7 C8 C9 106.1(2) . . ? C36 C31 C32 119.29(19) . . ? C36 C31 C26 121.15(19) . . ? C32 C31 C26 119.54(18) . . ? C35 C36 C31 119.8(2) . . ? C24 C23 C22 106.29(19) . . ? C13 C14 C15 120.5(2) . . ? C14 C13 C12 120.3(2) . . ? C10 C15 C14 119.7(2) . . ? C33 S2 C37 104.24(11) . . ? C34 C33 C32 119.6(2) . . ? C34 C33 S2 116.12(16) . . ? C32 C33 S2 124.26(18) . . ? F5 C21 F6 107.53(18) . . ? F5 C21 F4 107.24(18) . . ? F6 C21 F4 107.25(19) . . ? F5 C21 C20 110.67(17) . . ? F6 C21 C20 110.84(17) . . ? F4 C21 C20 113.07(18) . . ? C34 C35 C36 120.8(2) . . ? C35 C34 C33 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.691 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.081