Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'C. Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506-3701 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Attempted assembly of discrete coordination complexes into extended architectures using halogen bonding or halogen...halogen interactions ; loop_ _publ_author_name 'C. Aakeroy' 'John Desper' 'Curtis Moore' 'Nate Schultheiss' data_2 _database_code_depnum_ccdc_archive 'CCDC 633937' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-pyridyl)-2-(2,3,5,6-F4-4-I-phenyl)ethene ; _chemical_name_common 1-(4-pyridyl)-2-(2,3,5,6-F4-4-I-phenyl)ethene _chemical_melting_point ? _chemical_formula_moiety ; (C13 H6 F4 N I) ; _chemical_formula_sum 'C13 H6 F4 I N' _chemical_formula_weight 379.09 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmn2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y, z+1/2' '-x, y, z' _cell_length_a 12.0266(5) _cell_length_b 10.2443(4) _cell_length_c 4.9988(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 615.87(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4856 _cell_measurement_theta_min 3.93 _cell_measurement_theta_max 20.90 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6346 _exptl_absorpt_correction_T_max 0.8170 _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 14684 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.08 _reflns_number_total 1424 _reflns_number_gt 1208 _reflns_threshold_expression >2sigma(I) _reflns_Friedel_coverage 0.791 _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^)+(0.0300P)^2^+2.0000P] 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 constr _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 0.00(6) _refine_ls_number_reflns 1424 _refine_ls_number_parameters 132 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0737 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.009 _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 I1A I 0.0130(5) 0.1136(6) -0.3988(14) 0.0163(2) Uiso 0.213(15) 1 d PD A -1 C11A C 0.0128(14) 0.267(5) -0.118(10) 0.019(3) Uiso 0.213(15) 1 d PD A -1 C12A C 0.1115(15) 0.314(5) -0.016(11) 0.019(2) Uiso 0.213(15) 1 d PD A -1 C13A C 0.1160(15) 0.402(4) 0.178(8) 0.015(2) Uiso 0.213(15) 1 d PD A -1 C14A C 0.0206(15) 0.460(3) 0.289(6) 0.016(3) Uiso 0.213(15) 1 d PD A -1 C15A C -0.0766(15) 0.416(3) 0.192(6) 0.015(2) Uiso 0.213(15) 1 d PD A -1 C16A C -0.0812(14) 0.319(3) -0.013(7) 0.019(2) Uiso 0.213(15) 1 d PD A -1 F12A F 0.2074(14) 0.249(2) -0.081(5) 0.0274(19) Uiso 0.213(15) 1 d PD A -1 F13A F 0.2160(15) 0.431(2) 0.297(4) 0.0195(19) Uiso 0.213(15) 1 d PD A -1 F15A F -0.1728(16) 0.4867(18) 0.227(4) 0.0195(19) Uiso 0.213(15) 1 d PD A -1 F16A F -0.1815(14) 0.305(2) -0.140(4) 0.0274(19) Uiso 0.213(15) 1 d PD A -1 N21A N -0.001(5) 0.931(3) 1.221(6) 0.020(3) Uiso 0.43(3) 2 d SPD A -1 C22A C -0.122(2) 0.886(3) 1.136(7) 0.010(4) Uiso 0.213(15) 1 d PD A -1 H22A H -0.1852 0.9244 1.2088 0.012 Uiso 0.213(15) 1 calc PR A -1 C23A C -0.131(2) 0.783(5) 0.942(10) 0.028(2) Uiso 0.213(15) 1 d PD A -1 H23A H -0.1996 0.7493 0.8924 0.033 Uiso 0.213(15) 1 calc PR A -1 C24A C -0.0309(18) 0.735(6) 0.828(12) 0.019(3) Uiso 0.213(15) 1 d PD A -1 C25A C 0.070(2) 0.779(10) 0.93(2) 0.028(2) Uiso 0.213(15) 1 d PD A -1 H25A H 0.1371 0.7414 0.8791 0.033 Uiso 0.213(15) 1 calc PR A -1 C26A C 0.069(2) 0.878(3) 1.115(9) 0.010(4) Uiso 0.213(15) 1 d PD A -1 H26A H 0.1400 0.9073 1.1622 0.012 Uiso 0.213(15) 1 calc PR A -1 C27A C -0.0425(19) 0.624(3) 0.641(5) 0.020 Uiso 0.213(15) 1 d PD A -1 H27A H -0.1110 0.5823 0.6386 0.024 Uiso 0.213(15) 1 calc PR A -1 C28A C 0.0371(17) 0.577(2) 0.470(5) 0.011(4) Uiso 0.213(15) 1 d PD A -1 H28A H 0.1054 0.6196 0.4640 0.013 Uiso 0.213(15) 1 calc PR A -1 I1B I -0.0127(4) 0.1284(4) -0.4023(11) 0.0163(2) Uiso 0.287(15) 1 d PD A -2 C11B C -0.0098(15) 0.278(3) -0.113(8) 0.019(3) Uiso 0.287(15) 1 d PD A -2 C12B C -0.1070(13) 0.324(5) -0.002(9) 0.019(2) Uiso 0.287(15) 1 d PD A -2 C13B C -0.1093(14) 0.417(3) 0.179(7) 0.015(2) Uiso 0.287(15) 1 d PD A -2 C14B C -0.0126(16) 0.477(2) 0.281(5) 0.016(3) Uiso 0.287(15) 1 d PD A -2 C15B C 0.0834(14) 0.435(2) 0.172(4) 0.015(2) Uiso 0.287(15) 1 d PD A -2 C16B C 0.0853(14) 0.335(3) -0.028(6) 0.019(2) Uiso 0.287(15) 1 d PD A -2 F12B F -0.2060(14) 0.280(2) -0.104(5) 0.0274(19) Uiso 0.287(15) 1 d PD A -2 F13B F -0.2108(14) 0.465(2) 0.257(3) 0.0195(19) Uiso 0.287(15) 1 d PD A -2 F15B F 0.1837(13) 0.458(2) 0.295(4) 0.0195(19) Uiso 0.287(15) 1 d PD A -2 F16B F 0.1866(14) 0.278(2) -0.080(5) 0.0274(19) Uiso 0.287(15) 1 d PD A -2 N21B N -0.0219(19) 0.920(2) 1.243(5) 0.020(3) Uiso 0.287(15) 1 d PD A -2 C22B C 0.105(2) 0.892(3) 1.171(6) 0.010(4) Uiso 0.287(15) 1 d PD A -2 H22B H 0.1623 0.9354 1.2587 0.012 Uiso 0.287(15) 1 calc PR A -2 C23B C 0.1276(18) 0.797(4) 0.966(8) 0.028(2) Uiso 0.287(15) 1 d PD A -2 H23B H 0.2000 0.7779 0.9141 0.033 Uiso 0.287(15) 1 calc PR A -2 C24B C 0.0351(15) 0.735(5) 0.846(10) 0.019(3) Uiso 0.287(15) 1 d PD A -2 C25B C -0.0723(19) 0.774(8) 0.921(16) 0.028(2) Uiso 0.287(15) 1 d PD A -2 H25B H -0.1341 0.7436 0.8280 0.033 Uiso 0.287(15) 1 calc PR A -2 C26B C -0.084(2) 0.856(2) 1.134(6) 0.010(4) Uiso 0.287(15) 1 d PD A -2 H26B H -0.1562 0.8597 1.2024 0.012 Uiso 0.287(15) 1 calc PR A -2 C27B C 0.0577(14) 0.639(2) 0.632(5) 0.020 Uiso 0.287(15) 1 d PD A -2 H27B H 0.1308 0.6263 0.5773 0.024 Uiso 0.287(15) 1 calc PR A -2 C28B C -0.0235(14) 0.5709(17) 0.512(3) 0.011(4) Uiso 0.287(15) 1 d PD A -2 H28C H -0.0948 0.5827 0.5797 0.013 Uiso 0.287(15) 1 calc PR A -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 I1A C11A 2.108(11) . ? C11A C16A 1.353(17) . ? C11A C12A 1.379(16) . ? C12A C13A 1.324(13) . ? C12A F12A 1.372(11) . ? C13A F13A 1.374(11) . ? C13A C14A 1.407(14) . ? C14A C15A 1.344(15) . ? C14A C28A 1.512(15) . ? C15A F15A 1.374(11) . ? C15A C16A 1.432(13) . ? C16A F16A 1.371(12) . ? N21A C26A 1.14(3) . ? N21A C22A 1.59(4) . ? C22A C23A 1.43(2) . ? C22A H22A 0.9300 . ? C23A C24A 1.421(19) . ? C23A H23A 0.9300 . ? C24A C25A 1.40(2) . ? C24A C27A 1.471(19) . ? C25A C26A 1.36(2) . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? C27A C28A 1.373(9) . ? C27A H27A 0.9300 . ? C28A H28A 0.9300 . ? I1B C11B 2.106(10) . ? C11B C16B 1.355(17) . ? C11B C12B 1.376(16) . ? C12B C13B 1.321(13) . ? C12B F12B 1.369(13) . ? C13B F13B 1.372(13) . ? C13B C14B 1.408(15) . ? C14B C15B 1.346(15) . ? C14B C28B 1.511(14) . ? C15B F15B 1.375(13) . ? C15B C16B 1.432(13) . ? C16B F16B 1.375(14) . ? N21B C26B 1.14(3) . ? N21B C22B 1.59(3) . ? C22B C23B 1.44(2) . ? C22B H22B 0.9300 . ? C23B C24B 1.414(18) . ? C23B H23B 0.9300 . ? C24B C25B 1.402(19) . ? C24B C27B 1.479(18) . ? C25B C26B 1.36(2) . ? C25B H25B 0.9300 . ? C26B H26B 0.9300 . ? C27B C28B 1.343(11) . ? C27B H27B 0.9300 . ? C28B H28C 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16A C11A C12A 116.1(11) . . ? C16A C11A I1A 123.4(10) . . ? C12A C11A I1A 120.4(9) . . ? C13A C12A F12A 118.2(12) . . ? C13A C12A C11A 122.9(14) . . ? F12A C12A C11A 117.7(11) . . ? C12A C13A F13A 119.9(10) . . ? C12A C13A C14A 123.0(11) . . ? F13A C13A C14A 116.8(11) . . ? C15A C14A C13A 115.1(11) . . ? C15A C14A C28A 126.5(11) . . ? C13A C14A C28A 117.6(12) . . ? C14A C15A F15A 120.7(12) . . ? C14A C15A C16A 121.7(12) . . ? F15A C15A C16A 115.2(11) . . ? C11A C16A F16A 121.0(15) . . ? C11A C16A C15A 121.2(12) . . ? F16A C16A C15A 115.7(10) . . ? C26A N21A C22A 114.5(16) . . ? C23A C22A N21A 117.5(14) . . ? C23A C22A H22A 121.2 . . ? N21A C22A H22A 121.2 . . ? C24A C23A C22A 117.9(16) . . ? C24A C23A H23A 121.1 . . ? C22A C23A H23A 121.1 . . ? C25A C24A C23A 118.0(14) . . ? C25A C24A C27A 124.8(17) . . ? C23A C24A C27A 116.3(15) . . ? C26A C25A C24A 119.1(18) . . ? C26A C25A H25A 120.4 . . ? C24A C25A H25A 120.4 . . ? N21A C26A C25A 133(2) . . ? N21A C26A H26A 113.7 . . ? C25A C26A H26A 113.7 . . ? C28A C27A C24A 126.9(17) . . ? C28A C27A H27A 116.6 . . ? C24A C27A H27A 116.6 . . ? C27A C28A C14A 124.0(15) . . ? C27A C28A H28A 118.0 . . ? C14A C28A H28A 118.0 . . ? C16B C11B C12B 116.3(9) . . ? C16B C11B I1B 123.0(10) . . ? C12B C11B I1B 120.7(10) . . ? C13B C12B F12B 118.2(12) . . ? C13B C12B C11B 122.8(13) . . ? F12B C12B C11B 118.6(11) . . ? C12B C13B F13B 118.2(12) . . ? C12B C13B C14B 123.1(12) . . ? F13B C13B C14B 118.6(11) . . ? C15B C14B C13B 115.2(9) . . ? C15B C14B C28B 125.9(10) . . ? C13B C14B C28B 118.8(11) . . ? C14B C15B F15B 121.1(12) . . ? C14B C15B C16B 121.5(12) . . ? F15B C15B C16B 115.0(12) . . ? C11B C16B F16B 120.4(14) . . ? C11B C16B C15B 121.0(12) . . ? F16B C16B C15B 116.6(12) . . ? C26B N21B C22B 114.9(14) . . ? C23B C22B N21B 117.6(13) . . ? C23B C22B H22B 121.2 . . ? N21B C22B H22B 121.2 . . ? C24B C23B C22B 117.2(15) . . ? C24B C23B H23B 121.4 . . ? C22B C23B H23B 121.4 . . ? C25B C24B C23B 119.1(12) . . ? C25B C24B C27B 123.3(12) . . ? C23B C24B C27B 117.5(12) . . ? C26B C25B C24B 118.6(19) . . ? C26B C25B H25B 120.7 . . ? C24B C25B H25B 120.7 . . ? N21B C26B C25B 131(2) . . ? N21B C26B H26B 114.4 . . ? C25B C26B H26B 114.4 . . ? C28B C27B C24B 122.4(13) . . ? C28B C27B H27B 118.8 . . ? C24B C27B H27B 118.8 . . ? C27B C28B C14B 127.7(13) . . ? C27B C28B H28C 116.2 . . ? C14B C28B H28C 116.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16A C11A C12A C13A 1(10) . . . . ? I1A C11A C12A C13A -174(6) . . . . ? C16A C11A C12A F12A 169(5) . . . . ? I1A C11A C12A F12A -7(8) . . . . ? F12A C12A C13A F13A 3(9) . . . . ? C11A C12A C13A F13A 171(6) . . . . ? F12A C12A C13A C14A -170(5) . . . . ? C11A C12A C13A C14A -3(11) . . . . ? C12A C13A C14A C15A 2(8) . . . . ? F13A C13A C14A C15A -171(4) . . . . ? C12A C13A C14A C28A -169(6) . . . . ? F13A C13A C14A C28A 18(7) . . . . ? C13A C14A C15A F15A -162(4) . . . . ? C28A C14A C15A F15A 7(6) . . . . ? C13A C14A C15A C16A 0(6) . . . . ? C28A C14A C15A C16A 169(4) . . . . ? C12A C11A C16A F16A 163(5) . . . . ? I1A C11A C16A F16A -21(7) . . . . ? C12A C11A C16A C15A 0(8) . . . . ? I1A C11A C16A C15A 175(4) . . . . ? C14A C15A C16A C11A -1(7) . . . . ? F15A C15A C16A C11A 162(5) . . . . ? C14A C15A C16A F16A -165(4) . . . . ? F15A C15A C16A F16A -2(5) . . . . ? C26A N21A C22A C23A 1(7) . . . . ? N21A C22A C23A C24A -4(8) . . . . ? C22A C23A C24A C25A 7(13) . . . . ? C22A C23A C24A C27A 177(5) . . . . ? C23A C24A C25A C26A -8(17) . . . . ? C27A C24A C25A C26A -177(8) . . . . ? C22A N21A C26A C25A -2(11) . . . . ? C24A C25A C26A N21A 6(18) . . . . ? C25A C24A C27A C28A -24(13) . . . . ? C23A C24A C27A C28A 167(5) . . . . ? C24A C27A C28A C14A 178(5) . . . . ? C15A C14A C28A C27A 27(6) . . . . ? C13A C14A C28A C27A -164(4) . . . . ? C16B C11B C12B C13B -1(8) . . . . ? I1B C11B C12B C13B -180(5) . . . . ? C16B C11B C12B F12B 172(5) . . . . ? I1B C11B C12B F12B -7(7) . . . . ? F12B C12B C13B F13B 1(7) . . . . ? C11B C12B C13B F13B 173(5) . . . . ? F12B C12B C13B C14B -175(4) . . . . ? C11B C12B C13B C14B -2(8) . . . . ? C12B C13B C14B C15B 3(6) . . . . ? F13B C13B C14B C15B -172(4) . . . . ? C12B C13B C14B C28B -172(5) . . . . ? F13B C13B C14B C28B 13(5) . . . . ? C13B C14B C15B F15B -163(4) . . . . ? C28B C14B C15B F15B 12(5) . . . . ? C13B C14B C15B C16B -1(4) . . . . ? C28B C14B C15B C16B 173(3) . . . . ? C12B C11B C16B F16B 166(5) . . . . ? I1B C11B C16B F16B -15(6) . . . . ? C12B C11B C16B C15B 2(6) . . . . ? I1B C11B C16B C15B -179(3) . . . . ? C14B C15B C16B C11B -1(6) . . . . ? F15B C15B C16B C11B 162(4) . . . . ? C14B C15B C16B F16B -165(3) . . . . ? F15B C15B C16B F16B -2(5) . . . . ? C26B N21B C22B C23B 5(5) . . . . ? N21B C22B C23B C24B -1(6) . . . . ? C22B C23B C24B C25B 4(11) . . . . ? C22B C23B C24B C27B 179(4) . . . . ? C23B C24B C25B C26B -9(14) . . . . ? C27B C24B C25B C26B 176(6) . . . . ? C22B N21B C26B C25B -13(8) . . . . ? C24B C25B C26B N21B 16(13) . . . . ? C25B C24B C27B C28B -8(10) . . . . ? C23B C24B C27B C28B 177(4) . . . . ? C24B C27B C28B C14B 176(4) . . . . ? C15B C14B C28B C27B 7(5) . . . . ? C13B C14B C28B C27B -178(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.610 _refine_diff_density_min -0.799 _refine_diff_density_rms 0.122 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 633938' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N7 Cu(F6-acac)2 [1-(4-pyridyl)-2-(2,3,5,6-F4-4-Br-phenyl)ethene]2 ; _chemical_name_common ;N7 Cu(F6-acac)2 (1-(4-pyridyl)-2-(2,3,5,6-F4-4-Br- phenyl)ethene)2 ; _chemical_melting_point ? _chemical_formula_moiety ; Cu (C5 H O2 F6)2 (C13 H6 F4 N Br)2 ; _chemical_formula_sum 'C36 H14 Br2 Cu F20 N2 O4' _chemical_formula_weight 1141.85 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9889(3) _cell_length_b 9.0836(3) _cell_length_c 12.9622(5) _cell_angle_alpha 88.061(2) _cell_angle_beta 86.489(2) _cell_angle_gamma 67.894(2) _cell_volume 978.67(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 500 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 31.35 _exptl_crystal_description block _exptl_crystal_colour clear _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.220 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 555 _exptl_absorpt_coefficient_mu 2.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 1.000 _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 37237 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 33.50 _reflns_number_total 6622 _reflns_number_gt 5051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0400P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6622 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.0000 0.0000 0.0000 0.02120(7) Uani 1 2 d S . . Br1 Br 1.05164(2) -0.64745(3) 0.720492(15) 0.03886(7) Uani 1 1 d . . . N11 N 0.15612(18) -0.11443(18) 0.10542(12) 0.0239(3) Uani 1 1 d . . . C12 C 0.1642(2) -0.0432(2) 0.19296(15) 0.0282(4) Uani 1 1 d . . . H12 H 0.0930 0.0606 0.2046 0.034 Uiso 1 1 calc R . . C13 C 0.2738(2) -0.1178(2) 0.26626(15) 0.0293(4) Uani 1 1 d . . . H13 H 0.2759 -0.0645 0.3258 0.035 Uiso 1 1 calc R . . C14 C 0.3819(2) -0.2741(2) 0.25047(14) 0.0260(3) Uani 1 1 d . . . C15 C 0.3690(2) -0.3479(2) 0.16045(15) 0.0285(4) Uani 1 1 d . . . H15 H 0.4359 -0.4529 0.1478 0.034 Uiso 1 1 calc R . . C16 C 0.2571(2) -0.2650(2) 0.09043(15) 0.0266(4) Uani 1 1 d . . . H16 H 0.2515 -0.3155 0.0304 0.032 Uiso 1 1 calc R . . C17 C 0.5062(2) -0.3631(2) 0.32146(15) 0.0306(4) Uani 1 1 d . . . H17 H 0.5620 -0.4706 0.3087 0.037 Uiso 1 1 calc R . . C21 C 0.9022(2) -0.5433(3) 0.62240(14) 0.0298(4) Uani 1 1 d . . . C22 C 0.8578(3) -0.6294(3) 0.55316(16) 0.0327(4) Uani 1 1 d . . . F22 F 0.92387(18) -0.78765(16) 0.55401(11) 0.0464(3) Uani 1 1 d . . . C23 C 0.7439(3) -0.5538(2) 0.48224(15) 0.0314(4) Uani 1 1 d . . . F23 F 0.70515(18) -0.64754(15) 0.41985(11) 0.0457(3) Uani 1 1 d . . . C24 C 0.6694(2) -0.3891(2) 0.47508(14) 0.0273(4) Uani 1 1 d . . . C25 C 0.7196(2) -0.3051(2) 0.54426(15) 0.0296(4) Uani 1 1 d . . . F25 F 0.65849(16) -0.14587(15) 0.54018(10) 0.0401(3) Uani 1 1 d . . . C26 C 0.8322(2) -0.3792(3) 0.61619(14) 0.0314(4) Uani 1 1 d . . . F26 F 0.87519(17) -0.28969(17) 0.67875(10) 0.0453(3) Uani 1 1 d . . . C27 C 0.5458(2) -0.3024(2) 0.40309(15) 0.0285(4) Uani 1 1 d . . . H27 H 0.4896 -0.1948 0.4154 0.034 Uiso 1 1 calc R . . C31 C 0.3925(3) -0.1117(3) -0.23554(18) 0.0393(5) Uani 1 1 d . . . F31A F 0.42873(19) -0.26693(16) -0.23066(13) 0.0527(4) Uani 1 1 d . . . F31B F 0.3232(3) -0.0619(2) -0.32389(12) 0.0755(6) Uani 1 1 d . . . F31C F 0.5322(2) -0.0928(2) -0.24068(15) 0.0733(6) Uani 1 1 d . . . C32 C 0.2799(2) -0.0258(2) -0.14429(14) 0.0266(4) Uani 1 1 d . . . O32 O 0.17706(18) -0.08271(17) -0.11807(11) 0.0324(3) Uani 1 1 d . . . C33 C 0.3033(2) 0.1044(2) -0.10550(15) 0.0291(4) Uani 1 1 d . . . H33 H 0.3917 0.1263 -0.1313 0.035 Uiso 1 1 calc R . . C34 C 0.2004(2) 0.2044(2) -0.02942(14) 0.0257(3) Uani 1 1 d . . . O34 O 0.07624(16) 0.20009(17) 0.01386(11) 0.0315(3) Uani 1 1 d . . . C35 C 0.2488(3) 0.3410(3) 0.00278(17) 0.0345(4) Uani 1 1 d . . . F35A F 0.2421(2) 0.44262(17) -0.07592(12) 0.0522(4) Uani 1 1 d . . . F35B F 0.1564(2) 0.4243(2) 0.07927(15) 0.0724(6) Uani 1 1 d . . . F35C F 0.40056(19) 0.28924(19) 0.03044(13) 0.0555(4) 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 Cu1 0.02246(14) 0.02177(14) 0.02212(14) 0.00077(11) -0.00505(11) -0.01093(11) Br1 0.02799(10) 0.05876(15) 0.02365(10) 0.00693(9) -0.00608(7) -0.00914(9) N11 0.0261(7) 0.0232(7) 0.0258(7) 0.0006(6) -0.0056(6) -0.0124(6) C12 0.0306(9) 0.0260(9) 0.0282(9) -0.0013(7) -0.0070(7) -0.0099(7) C13 0.0330(9) 0.0303(9) 0.0266(9) -0.0014(7) -0.0088(7) -0.0129(8) C14 0.0262(8) 0.0283(9) 0.0267(8) 0.0030(7) -0.0071(7) -0.0131(7) C15 0.0310(9) 0.0239(8) 0.0311(9) 0.0004(7) -0.0077(7) -0.0100(7) C16 0.0308(9) 0.0246(8) 0.0266(8) -0.0013(7) -0.0061(7) -0.0120(7) C17 0.0323(9) 0.0303(9) 0.0293(9) 0.0022(7) -0.0097(8) -0.0109(8) C21 0.0229(8) 0.0447(11) 0.0202(8) 0.0047(7) -0.0023(6) -0.0109(8) C22 0.0323(10) 0.0377(11) 0.0280(9) 0.0061(8) -0.0043(8) -0.0130(8) F22 0.0563(8) 0.0340(7) 0.0460(8) 0.0090(6) -0.0170(7) -0.0121(6) C23 0.0354(10) 0.0356(10) 0.0271(9) 0.0021(7) -0.0082(8) -0.0171(8) F23 0.0619(9) 0.0338(7) 0.0471(8) 0.0037(6) -0.0265(7) -0.0214(6) C24 0.0255(8) 0.0353(10) 0.0224(8) 0.0023(7) -0.0039(7) -0.0127(7) C25 0.0277(9) 0.0354(10) 0.0239(8) -0.0027(7) -0.0022(7) -0.0095(8) F25 0.0454(7) 0.0341(6) 0.0361(7) -0.0057(5) -0.0128(6) -0.0076(5) C26 0.0273(9) 0.0455(11) 0.0208(8) -0.0039(8) -0.0030(7) -0.0123(8) F26 0.0478(8) 0.0517(8) 0.0351(7) -0.0106(6) -0.0163(6) -0.0142(6) C27 0.0282(9) 0.0317(9) 0.0274(9) 0.0034(7) -0.0076(7) -0.0126(7) C31 0.0497(13) 0.0341(11) 0.0357(11) -0.0063(8) -0.0012(9) -0.0171(10) F31A 0.0606(9) 0.0310(7) 0.0618(9) -0.0120(6) -0.0069(8) -0.0104(6) F31B 0.1088(15) 0.0590(10) 0.0291(7) -0.0052(7) -0.0082(9) 0.0034(10) F31C 0.0672(11) 0.0860(13) 0.0820(12) -0.0503(10) 0.0423(10) -0.0490(10) C32 0.0290(9) 0.0273(9) 0.0257(8) 0.0037(7) -0.0065(7) -0.0125(7) O32 0.0371(7) 0.0333(7) 0.0340(7) 0.0029(6) -0.0089(6) -0.0206(6) C33 0.0300(9) 0.0308(9) 0.0308(9) -0.0041(7) 0.0026(7) -0.0166(8) C34 0.0276(8) 0.0271(8) 0.0239(8) 0.0034(7) -0.0055(7) -0.0118(7) O34 0.0264(6) 0.0357(7) 0.0316(7) 0.0014(6) 0.0008(5) -0.0114(6) C35 0.0366(10) 0.0364(11) 0.0330(10) -0.0090(8) 0.0020(8) -0.0165(9) F35A 0.0742(10) 0.0377(7) 0.0549(9) 0.0037(6) -0.0098(8) -0.0321(7) F35B 0.0868(13) 0.0740(11) 0.0703(11) -0.0469(9) 0.0402(10) -0.0489(10) F35C 0.0526(9) 0.0577(9) 0.0662(10) -0.0082(8) -0.0226(8) -0.0285(7) _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 N11 1.9895(15) . ? Cu1 N11 1.9895(15) 2 ? Cu1 O32 2.0783(15) 2 ? Cu1 O32 2.0783(15) . ? Cu1 O34 2.1863(14) . ? Cu1 O34 2.1864(14) 2 ? Br1 C21 1.8677(19) . ? N11 C16 1.339(2) . ? N11 C12 1.344(2) . ? C12 C13 1.379(3) . ? C12 H12 0.9300 . ? C13 C14 1.400(3) . ? C13 H13 0.9300 . ? C14 C15 1.397(3) . ? C14 C17 1.464(3) . ? C15 C16 1.378(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C27 1.336(3) . ? C17 H17 0.9300 . ? C21 C22 1.380(3) . ? C21 C26 1.384(3) . ? C22 F22 1.333(3) . ? C22 C23 1.381(3) . ? C23 F23 1.343(2) . ? C23 C24 1.393(3) . ? C24 C25 1.395(3) . ? C24 C27 1.464(3) . ? C25 F25 1.341(2) . ? C25 C26 1.381(3) . ? C26 F26 1.337(2) . ? C27 H27 0.9300 . ? C31 F31B 1.321(3) . ? C31 F31A 1.322(3) . ? C31 F31C 1.328(3) . ? C31 C32 1.534(3) . ? C32 O32 1.244(2) . ? C32 C33 1.391(3) . ? C33 C34 1.404(3) . ? C33 H33 0.9300 . ? C34 O34 1.232(2) . ? C34 C35 1.538(3) . ? C35 F35B 1.312(2) . ? C35 F35C 1.333(3) . ? C35 F35A 1.341(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 N11 Cu1 N11 180.0 . 2 ? N11 Cu1 O32 88.95(6) . 2 ? N11 Cu1 O32 91.05(6) 2 2 ? N11 Cu1 O32 91.05(6) . . ? N11 Cu1 O32 88.95(6) 2 . ? O32 Cu1 O32 180.0 2 . ? N11 Cu1 O34 87.89(6) . . ? N11 Cu1 O34 92.11(6) 2 . ? O32 Cu1 O34 92.52(5) 2 . ? O32 Cu1 O34 87.48(5) . . ? N11 Cu1 O34 92.11(6) . 2 ? N11 Cu1 O34 87.89(6) 2 2 ? O32 Cu1 O34 87.48(5) 2 2 ? O32 Cu1 O34 92.52(5) . 2 ? O34 Cu1 O34 180.0 . 2 ? C16 N11 C12 118.19(16) . . ? C16 N11 Cu1 120.57(12) . . ? C12 N11 Cu1 121.23(13) . . ? N11 C12 C13 122.66(17) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 119.62(17) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 116.99(17) . . ? C15 C14 C17 118.73(17) . . ? C13 C14 C17 124.28(17) . . ? C16 C15 C14 119.94(17) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N11 C16 C15 122.57(17) . . ? N11 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C27 C17 C14 125.32(19) . . ? C27 C17 H17 117.3 . . ? C14 C17 H17 117.3 . . ? C22 C21 C26 117.71(18) . . ? C22 C21 Br1 120.31(16) . . ? C26 C21 Br1 121.98(15) . . ? F22 C22 C21 120.35(18) . . ? F22 C22 C23 118.82(19) . . ? C21 C22 C23 120.83(19) . . ? F23 C23 C22 116.62(18) . . ? F23 C23 C24 120.50(17) . . ? C22 C23 C24 122.87(19) . . ? C23 C24 C25 115.00(17) . . ? C23 C24 C27 125.37(18) . . ? C25 C24 C27 119.63(18) . . ? F25 C25 C26 118.25(18) . . ? F25 C25 C24 119.02(17) . . ? C26 C25 C24 122.72(19) . . ? F26 C26 C25 118.88(19) . . ? F26 C26 C21 120.27(18) . . ? C25 C26 C21 120.83(19) . . ? C17 C27 C24 126.22(19) . . ? C17 C27 H27 116.9 . . ? C24 C27 H27 116.9 . . ? F31B C31 F31A 106.55(19) . . ? F31B C31 F31C 108.2(2) . . ? F31A C31 F31C 105.7(2) . . ? F31B C31 C32 110.57(19) . . ? F31A C31 C32 111.92(19) . . ? F31C C31 C32 113.49(18) . . ? O32 C32 C33 129.73(19) . . ? O32 C32 C31 113.48(17) . . ? C33 C32 C31 116.76(17) . . ? C32 O32 Cu1 125.85(13) . . ? C32 C33 C34 123.44(18) . . ? C32 C33 H33 118.3 . . ? C34 C33 H33 118.3 . . ? O34 C34 C33 129.44(18) . . ? O34 C34 C35 115.58(17) . . ? C33 C34 C35 114.97(17) . . ? C34 O34 Cu1 122.93(13) . . ? F35B C35 F35C 107.95(19) . . ? F35B C35 F35A 107.03(19) . . ? F35C C35 F35A 104.76(18) . . ? F35B C35 C34 112.93(18) . . ? F35C C35 C34 112.13(17) . . ? F35A C35 C34 111.57(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O32 Cu1 N11 C16 134.89(14) 2 . . . ? O32 Cu1 N11 C16 -45.11(14) . . . . ? O34 Cu1 N11 C16 -132.55(14) . . . . ? O34 Cu1 N11 C16 47.45(14) 2 . . . ? O32 Cu1 N11 C12 -45.55(15) 2 . . . ? O32 Cu1 N11 C12 134.45(15) . . . . ? O34 Cu1 N11 C12 47.01(15) . . . . ? O34 Cu1 N11 C12 -132.99(15) 2 . . . ? C16 N11 C12 C13 1.3(3) . . . . ? Cu1 N11 C12 C13 -178.25(15) . . . . ? N11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 -1.6(3) . . . . ? C12 C13 C14 C17 178.14(19) . . . . ? C13 C14 C15 C16 2.1(3) . . . . ? C17 C14 C15 C16 -177.59(18) . . . . ? C12 N11 C16 C15 -0.7(3) . . . . ? Cu1 N11 C16 C15 178.86(15) . . . . ? C14 C15 C16 N11 -1.0(3) . . . . ? C15 C14 C17 C27 171.2(2) . . . . ? C13 C14 C17 C27 -8.5(3) . . . . ? C26 C21 C22 F22 178.50(19) . . . . ? Br1 C21 C22 F22 -1.6(3) . . . . ? C26 C21 C22 C23 -1.8(3) . . . . ? Br1 C21 C22 C23 178.12(16) . . . . ? F22 C22 C23 F23 1.5(3) . . . . ? C21 C22 C23 F23 -178.21(19) . . . . ? F22 C22 C23 C24 -179.49(19) . . . . ? C21 C22 C23 C24 0.8(3) . . . . ? F23 C23 C24 C25 179.78(18) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? F23 C23 C24 C27 0.3(3) . . . . ? C22 C23 C24 C27 -178.72(19) . . . . ? C23 C24 C25 F25 177.55(18) . . . . ? C27 C24 C25 F25 -2.9(3) . . . . ? C23 C24 C25 C26 -1.4(3) . . . . ? C27 C24 C25 C26 178.12(18) . . . . ? F25 C25 C26 F26 0.2(3) . . . . ? C24 C25 C26 F26 179.13(18) . . . . ? F25 C25 C26 C21 -178.52(18) . . . . ? C24 C25 C26 C21 0.4(3) . . . . ? C22 C21 C26 F26 -177.47(18) . . . . ? Br1 C21 C26 F26 2.6(3) . . . . ? C22 C21 C26 C25 1.2(3) . . . . ? Br1 C21 C26 C25 -178.73(15) . . . . ? C14 C17 C27 C24 179.90(18) . . . . ? C23 C24 C27 C17 -13.1(3) . . . . ? C25 C24 C27 C17 167.4(2) . . . . ? F31B C31 C32 O32 80.9(2) . . . . ? F31A C31 C32 O32 -37.7(3) . . . . ? F31C C31 C32 O32 -157.3(2) . . . . ? F31B C31 C32 C33 -97.3(2) . . . . ? F31A C31 C32 C33 144.13(19) . . . . ? F31C C31 C32 C33 24.6(3) . . . . ? C33 C32 O32 Cu1 -1.2(3) . . . . ? C31 C32 O32 Cu1 -179.03(13) . . . . ? N11 Cu1 O32 C32 -80.89(16) . . . . ? N11 Cu1 O32 C32 99.11(16) 2 . . . ? O34 Cu1 O32 C32 6.96(15) . . . . ? O34 Cu1 O32 C32 -173.04(15) 2 . . . ? O32 C32 C33 C34 -4.4(3) . . . . ? C31 C32 C33 C34 173.41(19) . . . . ? C32 C33 C34 O34 -1.5(3) . . . . ? C32 C33 C34 C35 179.76(18) . . . . ? C33 C34 O34 Cu1 10.7(3) . . . . ? C35 C34 O34 Cu1 -170.56(13) . . . . ? N11 Cu1 O34 C34 79.89(15) . . . . ? N11 Cu1 O34 C34 -100.11(15) 2 . . . ? O32 Cu1 O34 C34 168.75(15) 2 . . . ? O32 Cu1 O34 C34 -11.25(15) . . . . ? O34 C34 C35 F35B 5.9(3) . . . . ? C33 C34 C35 F35B -175.2(2) . . . . ? O34 C34 C35 F35C 128.08(19) . . . . ? C33 C34 C35 F35C -53.0(2) . . . . ? O34 C34 C35 F35A -114.8(2) . . . . ? C33 C34 C35 F35A 64.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 33.50 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 1.277 _refine_diff_density_min -0.997 _refine_diff_density_rms 0.074 #END data_4 _database_code_depnum_ccdc_archive 'CCDC 633939' _audit_creation_method SHELXL-97 _chemical_name_systematic ; NSBrCo Co(F6-acac)2 [1-(4-pyridyl)-2-(2,3,5,6-F4-4-Br-phenyl)ethene]2 ; _chemical_name_common ;NSBrCo Co(F6-acac)2 (1-(4-pyridyl)-2-(2,3,5,6-F4-4-Br- phenyl)ethene)2 ; _chemical_melting_point ? _chemical_formula_moiety ; Co (C5 H O2 F6)2 (C13 H6 F4 N Br)2 ; _chemical_formula_sum 'C36 H14 Br2 Co F20 N2 O4' _chemical_formula_weight 1137.24 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9245(4) _cell_length_b 9.0077(3) _cell_length_c 13.0921(5) _cell_angle_alpha 86.370(2) _cell_angle_beta 86.442(2) _cell_angle_gamma 70.214(2) _cell_volume 987.42(7) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.95 _exptl_crystal_description Block _exptl_crystal_colour lustrous _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.110 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.912 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 553 _exptl_absorpt_coefficient_mu 2.596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 1.000 _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 30628 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.14 _reflns_number_total 4360 _reflns_number_gt 3300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0400P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4360 _refine_ls_number_parameters 316 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 1.0000 0.5000 0.02665(13) Uani 1 2 d S . . Br1 Br 1.13575(4) -0.05103(3) -0.22269(2) 0.04813(12) Uani 1 1 d . . . N11 N 0.6226(2) 0.8349(2) 0.38913(16) 0.0295(5) Uani 1 1 d . . . C12 C 0.5550(3) 0.8261(3) 0.3020(2) 0.0348(6) Uani 1 1 d . . . H12 H 0.4531 0.8962 0.2904 0.042 Uiso 1 1 calc R . . C13 C 0.6286(3) 0.7189(3) 0.2295(2) 0.0365(6) Uani 1 1 d . . . H13 H 0.5770 0.7174 0.1703 0.044 Uiso 1 1 calc R . . C14 C 0.7814(3) 0.6120(3) 0.2449(2) 0.0330(6) Uani 1 1 d . . . C15 C 0.8523(3) 0.6246(3) 0.3340(2) 0.0342(6) Uani 1 1 d . . . H15 H 0.9555 0.5585 0.3466 0.041 Uiso 1 1 calc R . . C16 C 0.7703(3) 0.7343(3) 0.4034(2) 0.0325(6) Uani 1 1 d . . . H16 H 0.8194 0.7390 0.4631 0.039 Uiso 1 1 calc R . . C17 C 0.8686(3) 0.4893(3) 0.1741(2) 0.0375(6) Uani 1 1 d . . . H17 H 0.9750 0.4342 0.1864 0.045 Uiso 1 1 calc R . . C21 C 1.0373(4) 0.0977(3) -0.1248(2) 0.0380(7) Uani 1 1 d . . . C22 C 0.8742(4) 0.1744(3) -0.1202(2) 0.0386(7) Uani 1 1 d . . . F22 F 0.7815(2) 0.1392(2) -0.18475(13) 0.0544(5) Uani 1 1 d . . . C23 C 0.8051(3) 0.2856(3) -0.0488(2) 0.0348(6) Uani 1 1 d . . . F23 F 0.6453(2) 0.3534(2) -0.04659(13) 0.0477(4) Uani 1 1 d . . . C24 C 0.8912(3) 0.3281(3) 0.0219(2) 0.0332(6) Uani 1 1 d . . . C25 C 1.0552(4) 0.2470(3) 0.0159(2) 0.0387(7) Uani 1 1 d . . . F25 F 1.1510(2) 0.2790(2) 0.07983(14) 0.0558(5) Uani 1 1 d . . . C26 C 1.1257(4) 0.1352(3) -0.0544(2) 0.0399(7) Uani 1 1 d . . . F26 F 1.2832(2) 0.0620(2) -0.05396(14) 0.0563(5) Uani 1 1 d . . . C27 C 0.8082(3) 0.4502(3) 0.0936(2) 0.0350(6) Uani 1 1 d . . . H27 H 0.7018 0.5065 0.0818 0.042 Uiso 1 1 calc R . . C31A C 0.1579(3) 0.7551(3) 0.4973(2) 0.0369(7) Uani 0.885(11) 1 d PD A 1 F31A F 0.0512(4) 0.7630(5) 0.5748(2) 0.0512(11) Uani 0.885(11) 1 d PD A 1 F31B F 0.2051(3) 0.6052(4) 0.4686(3) 0.0551(12) Uani 0.885(11) 1 d PD A 1 F31C F 0.0825(5) 0.8450(5) 0.4209(3) 0.0663(14) Uani 0.885(11) 1 d PD A 1 C31B C 0.1579(3) 0.7551(3) 0.4973(2) 0.0369(7) Uani 0.060(5) 1 d PD A 2 F31D F 0.025(3) 0.850(4) 0.537(3) 0.0512(11) Uani 0.060(5) 1 d PD A 2 F31E F 0.166(5) 0.609(3) 0.517(3) 0.0551(12) Uani 0.060(5) 1 d PD A 2 F31F F 0.160(6) 0.773(6) 0.3962(13) 0.0663(14) Uani 0.060(5) 1 d PD A 2 C31C C 0.1579(3) 0.7551(3) 0.4973(2) 0.0369(7) Uani 0.057(9) 1 d PD A 3 F31G F 0.087(6) 0.698(7) 0.572(3) 0.0512(11) Uani 0.057(9) 1 d PD A 3 F31H F 0.053(5) 0.884(3) 0.460(4) 0.0551(12) Uani 0.057(9) 1 d PD A 3 F31I F 0.210(4) 0.658(5) 0.423(3) 0.0663(14) Uani 0.057(9) 1 d PD A 3 C32 C 0.2982(3) 0.8000(3) 0.53001(19) 0.0284(6) Uani 1 1 d . . . O32 O 0.3086(2) 0.9241(2) 0.48827(13) 0.0300(4) Uani 1 1 d . A . C33 C 0.3930(3) 0.7001(3) 0.6031(2) 0.0343(6) Uani 1 1 d . A . H33 H 0.3691 0.6109 0.6271 0.041 Uiso 1 1 calc R . . C34 C 0.5228(3) 0.7270(3) 0.64257(19) 0.0292(6) Uani 1 1 d . . . C35 C 0.6051(4) 0.6192(4) 0.7325(2) 0.0415(7) Uani 1 1 d . A . F35A F 0.5845(3) 0.4806(3) 0.73758(19) 0.0844(8) Uani 1 1 d . . . F35B F 0.5518(3) 0.6864(3) 0.81989(14) 0.0821(7) Uani 1 1 d . . . F35C F 0.7599(2) 0.5890(2) 0.72737(15) 0.0573(5) Uani 1 1 d . . . O34 O 0.5808(2) 0.8321(2) 0.61604(13) 0.0316(4) Uani 1 1 d . A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0267(3) 0.0283(3) 0.0295(3) -0.0045(2) -0.0030(2) -0.0142(2) Br1 0.0704(2) 0.03663(18) 0.03142(17) -0.00701(12) 0.00770(14) -0.01091(15) N11 0.0283(12) 0.0310(12) 0.0338(12) -0.0065(9) -0.0004(9) -0.0151(10) C12 0.0337(15) 0.0358(15) 0.0361(15) -0.0068(12) -0.0056(12) -0.0114(12) C13 0.0395(16) 0.0412(16) 0.0332(15) -0.0076(13) -0.0052(12) -0.0178(14) C14 0.0359(15) 0.0321(14) 0.0354(15) -0.0062(12) 0.0017(12) -0.0171(13) C15 0.0280(14) 0.0370(15) 0.0390(15) -0.0070(12) -0.0023(12) -0.0116(12) C16 0.0293(15) 0.0379(15) 0.0349(14) -0.0060(12) -0.0032(11) -0.0165(13) C17 0.0375(16) 0.0382(16) 0.0382(16) -0.0087(13) -0.0008(13) -0.0136(13) C21 0.0541(19) 0.0314(15) 0.0261(14) -0.0009(12) 0.0041(13) -0.0124(14) C22 0.0537(19) 0.0352(15) 0.0277(14) -0.0022(12) -0.0060(13) -0.0148(14) F22 0.0608(12) 0.0568(11) 0.0438(10) -0.0186(9) -0.0146(9) -0.0125(9) C23 0.0394(16) 0.0318(15) 0.0314(14) -0.0014(12) -0.0040(12) -0.0089(13) F23 0.0428(10) 0.0524(11) 0.0439(10) -0.0133(8) -0.0108(8) -0.0070(8) C24 0.0414(16) 0.0317(14) 0.0289(14) -0.0024(11) -0.0002(12) -0.0153(13) C25 0.0423(17) 0.0439(17) 0.0346(15) -0.0072(13) -0.0008(13) -0.0198(14) F25 0.0387(10) 0.0753(13) 0.0574(11) -0.0288(10) -0.0009(8) -0.0198(9) C26 0.0410(18) 0.0402(16) 0.0357(15) -0.0020(13) 0.0050(13) -0.0111(14) F26 0.0448(11) 0.0676(12) 0.0516(11) -0.0161(10) 0.0058(8) -0.0114(9) C27 0.0371(16) 0.0331(15) 0.0358(15) -0.0052(12) 0.0008(12) -0.0129(13) C31A 0.0391(16) 0.0397(16) 0.0393(16) 0.0010(13) -0.0108(13) -0.0216(14) F31A 0.0376(15) 0.072(3) 0.0565(13) -0.0082(15) 0.0012(11) -0.0335(17) F31B 0.0626(15) 0.0536(16) 0.064(3) -0.0236(16) -0.0065(14) -0.0341(11) F31C 0.072(2) 0.083(2) 0.069(2) 0.0339(19) -0.047(2) -0.057(2) C31B 0.0391(16) 0.0397(16) 0.0393(16) 0.0010(13) -0.0108(13) -0.0216(14) F31D 0.0376(15) 0.072(3) 0.0565(13) -0.0082(15) 0.0012(11) -0.0335(17) F31E 0.0626(15) 0.0536(16) 0.064(3) -0.0236(16) -0.0065(14) -0.0341(11) F31F 0.072(2) 0.083(2) 0.069(2) 0.0339(19) -0.047(2) -0.057(2) C31C 0.0391(16) 0.0397(16) 0.0393(16) 0.0010(13) -0.0108(13) -0.0216(14) F31G 0.0376(15) 0.072(3) 0.0565(13) -0.0082(15) 0.0012(11) -0.0335(17) F31H 0.0626(15) 0.0536(16) 0.064(3) -0.0236(16) -0.0065(14) -0.0341(11) F31I 0.072(2) 0.083(2) 0.069(2) 0.0339(19) -0.047(2) -0.057(2) C32 0.0284(14) 0.0327(14) 0.0287(13) -0.0082(11) -0.0001(11) -0.0153(12) O32 0.0275(9) 0.0315(10) 0.0347(10) -0.0027(8) -0.0048(8) -0.0139(8) C33 0.0381(16) 0.0349(15) 0.0373(15) 0.0031(12) -0.0070(12) -0.0218(13) C34 0.0270(14) 0.0311(14) 0.0289(14) -0.0055(11) 0.0002(11) -0.0086(11) C35 0.0389(17) 0.0450(18) 0.0423(17) 0.0006(14) -0.0098(13) -0.0152(14) F35A 0.1071(18) 0.0669(14) 0.0995(17) 0.0473(12) -0.0614(15) -0.0550(13) F35B 0.0768(15) 0.1064(18) 0.0330(10) 0.0002(11) -0.0046(10) 0.0085(13) F35C 0.0390(10) 0.0647(12) 0.0633(12) 0.0108(10) -0.0192(9) -0.0107(9) O34 0.0301(10) 0.0354(10) 0.0336(10) -0.0018(8) -0.0065(8) -0.0159(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O34 2.0545(17) 2_676 ? Co1 O34 2.0545(17) . ? Co1 O32 2.0607(16) 2_676 ? Co1 O32 2.0607(16) . ? Co1 N11 2.119(2) 2_676 ? Co1 N11 2.119(2) . ? Br1 C21 1.868(3) . ? N11 C16 1.339(3) . ? N11 C12 1.342(3) . ? C12 C13 1.369(4) . ? C12 H12 0.9300 . ? C13 C14 1.396(4) . ? C13 H13 0.9300 . ? C14 C15 1.390(4) . ? C14 C17 1.464(4) . ? C15 C16 1.371(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C27 1.331(4) . ? C17 H17 0.9300 . ? C21 C26 1.377(4) . ? C21 C22 1.383(4) . ? C22 F22 1.341(3) . ? C22 C23 1.373(4) . ? C23 F23 1.347(3) . ? C23 C24 1.388(4) . ? C24 C25 1.397(4) . ? C24 C27 1.460(4) . ? C25 F25 1.342(3) . ? C25 C26 1.368(4) . ? C26 F26 1.336(3) . ? C27 H27 0.9300 . ? C31A F31C 1.312(3) . ? C31A F31A 1.336(4) . ? C31A F31B 1.342(4) . ? C31A C32 1.531(4) . ? C32 O32 1.242(3) . ? C32 C33 1.385(4) . ? C33 C34 1.395(4) . ? C33 H33 0.9300 . ? C34 O34 1.247(3) . ? C34 C35 1.532(4) . ? C35 F35C 1.313(3) . ? C35 F35B 1.315(4) . ? C35 F35A 1.319(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 O34 Co1 O34 180.00(10) 2_676 . ? O34 Co1 O32 89.23(7) 2_676 2_676 ? O34 Co1 O32 90.77(7) . 2_676 ? O34 Co1 O32 90.77(7) 2_676 . ? O34 Co1 O32 89.23(7) . . ? O32 Co1 O32 180.0 2_676 . ? O34 Co1 N11 90.75(8) 2_676 2_676 ? O34 Co1 N11 89.25(8) . 2_676 ? O32 Co1 N11 87.41(7) 2_676 2_676 ? O32 Co1 N11 92.59(7) . 2_676 ? O34 Co1 N11 89.25(8) 2_676 . ? O34 Co1 N11 90.75(8) . . ? O32 Co1 N11 92.59(7) 2_676 . ? O32 Co1 N11 87.41(7) . . ? N11 Co1 N11 180.0 2_676 . ? C16 N11 C12 117.2(2) . . ? C16 N11 Co1 121.44(17) . . ? C12 N11 Co1 121.34(18) . . ? N11 C12 C13 123.2(3) . . ? N11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C12 C13 C14 119.8(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 116.7(2) . . ? C15 C14 C17 119.1(2) . . ? C13 C14 C17 124.2(2) . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N11 C16 C15 123.0(2) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? C27 C17 C14 125.5(3) . . ? C27 C17 H17 117.3 . . ? C14 C17 H17 117.3 . . ? C26 C21 C22 117.5(3) . . ? C26 C21 Br1 120.8(2) . . ? C22 C21 Br1 121.7(2) . . ? F22 C22 C23 119.2(3) . . ? F22 C22 C21 120.2(2) . . ? C23 C22 C21 120.6(3) . . ? F23 C23 C22 117.8(2) . . ? F23 C23 C24 118.9(2) . . ? C22 C23 C24 123.3(3) . . ? C23 C24 C25 114.6(2) . . ? C23 C24 C27 119.6(3) . . ? C25 C24 C27 125.8(2) . . ? F25 C25 C26 117.2(3) . . ? F25 C25 C24 120.0(2) . . ? C26 C25 C24 122.8(3) . . ? F26 C26 C25 118.8(3) . . ? F26 C26 C21 119.9(3) . . ? C25 C26 C21 121.2(3) . . ? C17 C27 C24 126.9(3) . . ? C17 C27 H27 116.5 . . ? C24 C27 H27 116.5 . . ? F31C C31A F31A 107.5(3) . . ? F31C C31A F31B 107.3(3) . . ? F31A C31A F31B 105.3(2) . . ? F31C C31A C32 113.2(2) . . ? F31A C31A C32 111.4(2) . . ? F31B C31A C32 111.7(2) . . ? O32 C32 C33 129.0(2) . . ? O32 C32 C31A 114.8(2) . . ? C33 C32 C31A 116.2(2) . . ? C32 O32 Co1 124.15(16) . . ? C32 C33 C34 123.1(2) . . ? C32 C33 H33 118.5 . . ? C34 C33 H33 118.5 . . ? O34 C34 C33 128.4(2) . . ? O34 C34 C35 113.7(2) . . ? C33 C34 C35 117.8(2) . . ? F35C C35 F35B 106.6(2) . . ? F35C C35 F35A 105.9(3) . . ? F35B C35 F35A 107.8(3) . . ? F35C C35 C34 112.2(2) . . ? F35B C35 C34 110.6(2) . . ? F35A C35 C34 113.3(2) . . ? C34 O34 Co1 124.84(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O34 Co1 N11 C16 138.39(19) 2_676 . . . ? O34 Co1 N11 C16 -41.61(19) . . . . ? O32 Co1 N11 C16 49.20(19) 2_676 . . . ? O32 Co1 N11 C16 -130.80(19) . . . . ? O34 Co1 N11 C12 -42.2(2) 2_676 . . . ? O34 Co1 N11 C12 137.8(2) . . . . ? O32 Co1 N11 C12 -131.3(2) 2_676 . . . ? O32 Co1 N11 C12 48.7(2) . . . . ? C16 N11 C12 C13 1.0(4) . . . . ? Co1 N11 C12 C13 -178.5(2) . . . . ? N11 C12 C13 C14 0.1(4) . . . . ? C12 C13 C14 C15 -1.7(4) . . . . ? C12 C13 C14 C17 177.9(3) . . . . ? C13 C14 C15 C16 2.3(4) . . . . ? C17 C14 C15 C16 -177.3(2) . . . . ? C12 N11 C16 C15 -0.4(4) . . . . ? Co1 N11 C16 C15 179.1(2) . . . . ? C14 C15 C16 N11 -1.3(4) . . . . ? C15 C14 C17 C27 170.6(3) . . . . ? C13 C14 C17 C27 -9.0(5) . . . . ? C26 C21 C22 F22 -177.9(3) . . . . ? Br1 C21 C22 F22 2.3(4) . . . . ? C26 C21 C22 C23 1.1(4) . . . . ? Br1 C21 C22 C23 -178.7(2) . . . . ? F22 C22 C23 F23 0.7(4) . . . . ? C21 C22 C23 F23 -178.4(2) . . . . ? F22 C22 C23 C24 179.1(3) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? F23 C23 C24 C25 177.7(2) . . . . ? C22 C23 C24 C25 -0.7(4) . . . . ? F23 C23 C24 C27 -3.0(4) . . . . ? C22 C23 C24 C27 178.6(3) . . . . ? C23 C24 C25 F25 179.4(2) . . . . ? C27 C24 C25 F25 0.1(4) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C27 C24 C25 C26 -179.0(3) . . . . ? F25 C25 C26 F26 1.6(4) . . . . ? C24 C25 C26 F26 -179.2(3) . . . . ? F25 C25 C26 C21 -178.3(3) . . . . ? C24 C25 C26 C21 0.9(5) . . . . ? C22 C21 C26 F26 178.5(2) . . . . ? Br1 C21 C26 F26 -1.7(4) . . . . ? C22 C21 C26 C25 -1.6(4) . . . . ? Br1 C21 C26 C25 178.2(2) . . . . ? C14 C17 C27 C24 -179.6(3) . . . . ? C23 C24 C27 C17 170.3(3) . . . . ? C25 C24 C27 C17 -10.4(5) . . . . ? F31C C31A C32 O32 7.9(5) . . . . ? F31A C31A C32 O32 -113.5(3) . . . . ? F31B C31A C32 O32 129.1(3) . . . . ? F31C C31A C32 C33 -173.6(4) . . . . ? F31A C31A C32 C33 65.0(4) . . . . ? F31B C31A C32 C33 -52.4(4) . . . . ? C33 C32 O32 Co1 10.7(4) . . . . ? C31A C32 O32 Co1 -171.00(17) . . . . ? O34 Co1 O32 C32 167.83(19) 2_676 . . . ? O34 Co1 O32 C32 -12.17(19) . . . . ? N11 Co1 O32 C32 -101.39(19) 2_676 . . . ? N11 Co1 O32 C32 78.61(19) . . . . ? O32 C32 C33 C34 -0.2(5) . . . . ? C31A C32 C33 C34 -178.4(2) . . . . ? C32 C33 C34 O34 -5.3(5) . . . . ? C32 C33 C34 C35 172.5(3) . . . . ? O34 C34 C35 F35C -37.8(3) . . . . ? C33 C34 C35 F35C 144.0(3) . . . . ? O34 C34 C35 F35B 81.1(3) . . . . ? C33 C34 C35 F35B -97.1(3) . . . . ? O34 C34 C35 F35A -157.7(3) . . . . ? C33 C34 C35 F35A 24.1(4) . . . . ? C33 C34 O34 Co1 -1.2(4) . . . . ? C35 C34 O34 Co1 -179.15(17) . . . . ? O32 Co1 O34 C34 -172.2(2) 2_676 . . . ? O32 Co1 O34 C34 7.8(2) . . . . ? N11 Co1 O34 C34 100.4(2) 2_676 . . . ? N11 Co1 O34 C34 -79.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.708 _refine_diff_density_min -0.718 _refine_diff_density_rms 0.069 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 633940' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N3 Cu(F6-acac)2 [1-(4-pyridyl)-2-(2,3,5,6-F4-4-I-phenyl)ethene]2 ; _chemical_name_common ;N3 Cu(F6-acac)2 (1-(4-pyridyl)-2-(2,3,5,6-F4-4-I- phenyl)ethene)2 ; _chemical_melting_point ? _chemical_formula_moiety ; Cu (C5 H O2 F6)2 (C13 H6 F4 N I)2 ; _chemical_formula_sum 'C36 H14 Cu F20 I2 N2 O4' _chemical_formula_weight 1235.83 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0352(4) _cell_length_b 9.0357(4) _cell_length_c 13.2174(6) _cell_angle_alpha 87.447(2) _cell_angle_beta 88.530(2) _cell_angle_gamma 69.506(2) _cell_volume 1009.70(8) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9342 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 32.50 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.170 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.032 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 591 _exptl_absorpt_coefficient_mu 2.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 1.000 _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 35349 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 33.29 _reflns_number_total 7467 _reflns_number_gt 5932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0300P)^2^+1.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7467 _refine_ls_number_parameters 308 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.039 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.02062(7) Uani 1 2 d S . . I1 I 0.64572(2) -0.552468(17) -0.222903(11) 0.03433(5) Uani 1 1 d . . . N11 N 0.1109(2) 0.3461(2) 0.39568(13) 0.0232(3) Uani 1 1 d . . . C12 C 0.0393(3) 0.3373(3) 0.30939(17) 0.0272(4) Uani 1 1 d . . . H12 H -0.0636 0.4059 0.2985 0.033 Uiso 1 1 calc R . . C13 C 0.1123(3) 0.2305(3) 0.23643(17) 0.0280(4) Uani 1 1 d . . . H13 H 0.0590 0.2280 0.1776 0.034 Uiso 1 1 calc R . . C14 C 0.2664(3) 0.1261(3) 0.25111(16) 0.0251(4) Uani 1 1 d . . . C15 C 0.3407(3) 0.1387(3) 0.33996(17) 0.0264(4) Uani 1 1 d . . . H15 H 0.4444 0.0733 0.3521 0.032 Uiso 1 1 calc R . . C16 C 0.2599(2) 0.2484(3) 0.40983(16) 0.0255(4) Uani 1 1 d . . . H16 H 0.3109 0.2546 0.4689 0.031 Uiso 1 1 calc R . . C17 C 0.3535(3) 0.0053(3) 0.18025(17) 0.0286(4) Uani 1 1 d . . . H17 H 0.4599 -0.0490 0.1932 0.034 Uiso 1 1 calc R . . C21 C 0.5308(3) -0.3872(3) -0.11658(16) 0.0272(4) Uani 1 1 d . . . C22 C 0.6161(3) -0.3399(3) -0.04782(17) 0.0293(4) Uani 1 1 d . . . F22 F 0.77369(17) -0.4026(2) -0.04756(12) 0.0453(4) Uani 1 1 d . . . C23 C 0.5425(3) -0.2272(3) 0.02156(17) 0.0289(4) Uani 1 1 d . . . F23 F 0.63549(17) -0.1866(2) 0.08376(12) 0.0437(4) Uani 1 1 d . . . C24 C 0.3788(3) -0.1545(3) 0.02730(16) 0.0254(4) Uani 1 1 d . . . C25 C 0.2949(3) -0.2062(3) -0.04203(17) 0.0280(4) Uani 1 1 d . . . F25 F 0.13633(17) -0.14613(19) -0.04005(11) 0.0395(3) Uani 1 1 d . . . C26 C 0.3683(3) -0.3190(3) -0.11173(16) 0.0289(4) Uani 1 1 d . . . F26 F 0.27776(18) -0.36244(19) -0.17443(11) 0.0427(4) Uani 1 1 d . . . C27 C 0.2933(3) -0.0337(3) 0.09842(17) 0.0276(4) Uani 1 1 d . . . H27 H 0.1869 0.0212 0.0856 0.033 Uiso 1 1 calc R . . C31 C -0.1169(3) 0.8904(4) 0.2690(2) 0.0407(6) Uani 1 1 d D . . F31A F -0.0724(3) 0.8203(3) 0.18165(14) 0.0813(7) Uani 1 1 d D . . F31B F -0.0928(3) 1.0267(3) 0.26330(18) 0.0781(7) Uani 1 1 d D . . F31C F -0.27156(19) 0.9265(2) 0.27559(15) 0.0549(5) Uani 1 1 d D . . C32 C -0.0307(3) 0.7800(3) 0.35674(17) 0.0275(4) Uani 1 1 d . . . O32 O -0.08731(19) 0.6763(2) 0.38164(13) 0.0331(4) Uani 1 1 d . . . C33 C 0.1013(3) 0.8044(3) 0.39557(18) 0.0293(4) Uani 1 1 d . A . H33 H 0.1252 0.8913 0.3707 0.035 Uiso 1 1 calc R . . C34 C 0.1988(3) 0.7054(3) 0.46943(17) 0.0273(4) Uani 1 1 d . . . O34 O 0.1939(2) 0.58135(19) 0.51035(13) 0.0318(3) Uani 1 1 d . A . C35 C 0.3345(3) 0.7553(3) 0.5046(2) 0.0397(6) Uani 0.869(4) 1 d PD A 1 F35A F 0.2842(3) 0.9108(3) 0.52667(19) 0.0602(7) Uani 0.869(4) 1 d PD A 1 F35B F 0.4390(2) 0.7510(3) 0.42920(18) 0.0647(8) Uani 0.869(4) 1 d PD A 1 F35C F 0.4085(4) 0.6780(4) 0.5824(3) 0.0994(16) Uani 0.869(4) 1 d PD A 1 C35B C 0.3345(3) 0.7553(3) 0.5046(2) 0.0397(6) Uani 0.131(4) 1 d PD A 2 F35D F 0.4626(13) 0.6212(13) 0.4988(11) 0.044(4) Uiso 0.131(4) 1 d PD A 2 F35E F 0.350(2) 0.8737(16) 0.4699(13) 0.060(5) Uiso 0.131(4) 1 d PD A 2 F35F F 0.309(2) 0.7566(19) 0.6048(9) 0.057(4) Uiso 0.131(4) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02070(16) 0.02171(16) 0.02063(16) -0.00597(13) 0.00227(12) -0.00845(13) I1 0.05031(10) 0.02373(8) 0.02418(8) -0.00589(5) 0.00860(6) -0.00700(6) N11 0.0223(8) 0.0249(8) 0.0235(8) -0.0064(7) 0.0021(6) -0.0092(7) C12 0.0239(10) 0.0294(11) 0.0273(10) -0.0078(8) -0.0006(8) -0.0074(8) C13 0.0286(10) 0.0311(11) 0.0245(10) -0.0088(8) -0.0007(8) -0.0098(9) C14 0.0268(10) 0.0249(10) 0.0253(10) -0.0078(8) 0.0047(8) -0.0109(8) C15 0.0236(10) 0.0277(10) 0.0266(10) -0.0066(8) 0.0020(8) -0.0068(8) C16 0.0243(10) 0.0292(10) 0.0234(10) -0.0069(8) 0.0003(8) -0.0094(8) C17 0.0267(10) 0.0289(11) 0.0278(11) -0.0099(8) 0.0038(8) -0.0062(9) C21 0.0380(12) 0.0207(9) 0.0203(9) -0.0027(7) 0.0044(8) -0.0070(9) C22 0.0295(11) 0.0297(11) 0.0261(10) -0.0065(8) 0.0061(8) -0.0068(9) F22 0.0286(7) 0.0575(10) 0.0441(9) -0.0204(8) 0.0073(6) -0.0063(7) C23 0.0301(11) 0.0324(11) 0.0254(10) -0.0096(9) 0.0031(8) -0.0120(9) F23 0.0298(7) 0.0599(10) 0.0435(9) -0.0273(8) 0.0030(6) -0.0154(7) C24 0.0298(10) 0.0251(10) 0.0213(9) -0.0055(8) 0.0023(8) -0.0091(8) C25 0.0295(11) 0.0273(10) 0.0242(10) -0.0039(8) -0.0010(8) -0.0057(9) F25 0.0285(7) 0.0458(9) 0.0379(8) -0.0146(7) -0.0047(6) -0.0031(6) C26 0.0378(12) 0.0265(10) 0.0212(10) -0.0047(8) -0.0018(8) -0.0090(9) F26 0.0433(8) 0.0473(9) 0.0357(8) -0.0191(7) -0.0068(6) -0.0110(7) C27 0.0301(11) 0.0262(10) 0.0261(10) -0.0073(8) 0.0033(8) -0.0087(9) C31 0.0323(12) 0.0507(16) 0.0363(13) -0.0035(11) -0.0054(10) -0.0106(12) F31A 0.0616(13) 0.1188(19) 0.0307(9) -0.0107(11) -0.0061(9) 0.0111(13) F31B 0.0840(15) 0.0705(13) 0.0921(16) 0.0474(12) -0.0513(13) -0.0451(12) F31C 0.0293(8) 0.0605(11) 0.0667(12) -0.0096(9) -0.0113(8) -0.0037(8) C32 0.0264(10) 0.0289(11) 0.0272(10) -0.0076(8) 0.0040(8) -0.0090(9) O32 0.0316(8) 0.0371(9) 0.0359(9) -0.0109(7) 0.0053(7) -0.0178(7) C33 0.0312(11) 0.0295(11) 0.0304(11) 0.0021(9) -0.0033(9) -0.0149(9) C34 0.0278(10) 0.0288(10) 0.0247(10) -0.0039(8) 0.0029(8) -0.0091(9) O34 0.0350(9) 0.0280(8) 0.0293(8) 0.0001(6) 0.0044(7) -0.0076(7) C35 0.0371(13) 0.0463(15) 0.0371(14) 0.0008(11) -0.0091(11) -0.0161(12) F35A 0.0643(14) 0.0606(14) 0.0675(16) -0.0242(11) -0.0066(12) -0.0336(12) F35B 0.0413(12) 0.102(2) 0.0659(15) -0.0233(14) 0.0094(10) -0.0418(13) F35C 0.108(3) 0.117(3) 0.099(3) 0.069(2) -0.081(2) -0.075(2) C35B 0.0371(13) 0.0463(15) 0.0371(14) 0.0008(11) -0.0091(11) -0.0161(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 N11 1.9907(17) 2_566 ? Cu1 N11 1.9907(17) . ? Cu1 O34 2.1330(17) 2_566 ? Cu1 O34 2.1331(17) . ? Cu1 O32 2.1373(18) 2_566 ? Cu1 O32 2.1374(18) . ? I1 C21 2.076(2) . ? N11 C16 1.339(3) . ? N11 C12 1.345(3) . ? C12 C13 1.379(3) . ? C12 H12 0.9300 . ? C13 C14 1.394(3) . ? C13 H13 0.9300 . ? C14 C15 1.396(3) . ? C14 C17 1.463(3) . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C27 1.337(3) . ? C17 H17 0.9300 . ? C21 C22 1.379(3) . ? C21 C26 1.380(3) . ? C22 F22 1.336(3) . ? C22 C23 1.378(3) . ? C23 F23 1.339(2) . ? C23 C24 1.394(3) . ? C24 C25 1.398(3) . ? C24 C27 1.461(3) . ? C25 F25 1.343(3) . ? C25 C26 1.380(3) . ? C26 F26 1.341(2) . ? C27 H27 0.9300 . ? C31 F31C 1.320(3) . ? C31 F31B 1.322(3) . ? C31 F31A 1.325(3) . ? C31 C32 1.532(4) . ? C32 O32 1.244(3) . ? C32 C33 1.400(3) . ? C33 C34 1.394(3) . ? C33 H33 0.9300 . ? C34 O34 1.237(3) . ? C34 C35 1.535(3) . ? C35 F35C 1.280(3) . ? C35 F35B 1.347(3) . ? C35 F35A 1.360(4) . ? 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 N11 Cu1 N11 180.0 2_566 . ? N11 Cu1 O34 92.18(6) 2_566 2_566 ? N11 Cu1 O34 87.82(6) . 2_566 ? N11 Cu1 O34 87.82(6) 2_566 . ? N11 Cu1 O34 92.18(6) . . ? O34 Cu1 O34 180.0 2_566 . ? N11 Cu1 O32 88.90(7) 2_566 2_566 ? N11 Cu1 O32 91.10(7) . 2_566 ? O34 Cu1 O32 87.06(6) 2_566 2_566 ? O34 Cu1 O32 92.94(6) . 2_566 ? N11 Cu1 O32 91.10(7) 2_566 . ? N11 Cu1 O32 88.90(7) . . ? O34 Cu1 O32 92.94(6) 2_566 . ? O34 Cu1 O32 87.06(6) . . ? O32 Cu1 O32 180.0 2_566 . ? C16 N11 C12 118.16(18) . . ? C16 N11 Cu1 120.54(14) . . ? C12 N11 Cu1 121.31(15) . . ? N11 C12 C13 122.6(2) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 119.8(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 117.07(19) . . ? C13 C14 C17 124.4(2) . . ? C15 C14 C17 118.6(2) . . ? C16 C15 C14 119.9(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N11 C16 C15 122.43(19) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C27 C17 C14 125.6(2) . . ? C27 C17 H17 117.2 . . ? C14 C17 H17 117.2 . . ? C22 C21 C26 117.18(19) . . ? C22 C21 I1 120.51(17) . . ? C26 C21 I1 122.31(16) . . ? F22 C22 C23 118.2(2) . . ? F22 C22 C21 120.3(2) . . ? C23 C22 C21 121.5(2) . . ? F23 C23 C22 117.1(2) . . ? F23 C23 C24 120.26(19) . . ? C22 C23 C24 122.6(2) . . ? C23 C24 C25 114.80(19) . . ? C23 C24 C27 125.47(19) . . ? C25 C24 C27 119.7(2) . . ? F25 C25 C26 118.32(19) . . ? F25 C25 C24 118.96(19) . . ? C26 C25 C24 122.7(2) . . ? F26 C26 C21 120.42(19) . . ? F26 C26 C25 118.4(2) . . ? C21 C26 C25 121.2(2) . . ? C17 C27 C24 126.1(2) . . ? C17 C27 H27 116.9 . . ? C24 C27 H27 116.9 . . ? F31C C31 F31B 106.0(2) . . ? F31C C31 F31A 106.3(2) . . ? F31B C31 F31A 108.2(3) . . ? F31C C31 C32 112.1(2) . . ? F31B C31 C32 113.7(2) . . ? F31A C31 C32 110.2(2) . . ? O32 C32 C33 128.9(2) . . ? O32 C32 C31 113.8(2) . . ? C33 C32 C31 117.3(2) . . ? C32 O32 Cu1 125.07(15) . . ? C34 C33 C32 123.6(2) . . ? C34 C33 H33 118.2 . . ? C32 C33 H33 118.2 . . ? O34 C34 C33 129.6(2) . . ? O34 C34 C35 114.7(2) . . ? C33 C34 C35 115.7(2) . . ? C34 O34 Cu1 124.42(15) . . ? F35C C35 F35B 109.3(3) . . ? F35C C35 F35A 106.6(3) . . ? F35B C35 F35A 100.9(2) . . ? F35C C35 C34 115.2(2) . . ? F35B C35 C34 111.8(2) . . ? F35A C35 C34 112.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O34 Cu1 N11 C16 -130.85(17) 2_566 . . . ? O34 Cu1 N11 C16 49.15(17) . . . . ? O32 Cu1 N11 C16 -43.84(16) 2_566 . . . ? O32 Cu1 N11 C16 136.16(16) . . . . ? O34 Cu1 N11 C12 49.24(17) 2_566 . . . ? O34 Cu1 N11 C12 -130.75(17) . . . . ? O32 Cu1 N11 C12 136.26(17) 2_566 . . . ? O32 Cu1 N11 C12 -43.74(17) . . . . ? C16 N11 C12 C13 1.0(3) . . . . ? Cu1 N11 C12 C13 -179.06(17) . . . . ? N11 C12 C13 C14 0.1(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C12 C13 C14 C17 178.2(2) . . . . ? C13 C14 C15 C16 1.6(3) . . . . ? C17 C14 C15 C16 -178.1(2) . . . . ? C12 N11 C16 C15 -0.8(3) . . . . ? Cu1 N11 C16 C15 179.26(16) . . . . ? C14 C15 C16 N11 -0.5(3) . . . . ? C13 C14 C17 C27 -7.9(4) . . . . ? C15 C14 C17 C27 171.8(2) . . . . ? C26 C21 C22 F22 179.2(2) . . . . ? I1 C21 C22 F22 -1.4(3) . . . . ? C26 C21 C22 C23 -1.2(3) . . . . ? I1 C21 C22 C23 178.17(18) . . . . ? F22 C22 C23 F23 1.0(3) . . . . ? C21 C22 C23 F23 -178.6(2) . . . . ? F22 C22 C23 C24 179.9(2) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? F23 C23 C24 C25 179.6(2) . . . . ? C22 C23 C24 C25 0.7(3) . . . . ? F23 C23 C24 C27 -0.7(4) . . . . ? C22 C23 C24 C27 -179.6(2) . . . . ? C23 C24 C25 F25 178.1(2) . . . . ? C27 C24 C25 F25 -1.6(3) . . . . ? C23 C24 C25 C26 -0.8(3) . . . . ? C27 C24 C25 C26 179.5(2) . . . . ? C22 C21 C26 F26 -178.2(2) . . . . ? I1 C21 C26 F26 2.4(3) . . . . ? C22 C21 C26 C25 1.1(3) . . . . ? I1 C21 C26 C25 -178.25(17) . . . . ? F25 C25 C26 F26 0.4(3) . . . . ? C24 C25 C26 F26 179.2(2) . . . . ? F25 C25 C26 C21 -179.0(2) . . . . ? C24 C25 C26 C21 -0.1(4) . . . . ? C14 C17 C27 C24 -179.7(2) . . . . ? C23 C24 C27 C17 -13.2(4) . . . . ? C25 C24 C27 C17 166.5(2) . . . . ? F31C C31 C32 O32 39.4(3) . . . . ? F31B C31 C32 O32 159.6(2) . . . . ? F31A C31 C32 O32 -78.8(3) . . . . ? F31C C31 C32 C33 -142.6(2) . . . . ? F31B C31 C32 C33 -22.5(3) . . . . ? F31A C31 C32 C33 99.2(3) . . . . ? C33 C32 O32 Cu1 2.1(3) . . . . ? C31 C32 O32 Cu1 179.78(15) . . . . ? N11 Cu1 O32 C32 80.11(18) 2_566 . . . ? N11 Cu1 O32 C32 -99.89(18) . . . . ? O34 Cu1 O32 C32 172.35(18) 2_566 . . . ? O34 Cu1 O32 C32 -7.65(18) . . . . ? O32 C32 C33 C34 3.1(4) . . . . ? C31 C32 C33 C34 -174.5(2) . . . . ? C32 C33 C34 O34 3.0(4) . . . . ? C32 C33 C34 C35 -178.1(2) . . . . ? C33 C34 O34 Cu1 -12.6(3) . . . . ? C35 C34 O34 Cu1 168.43(16) . . . . ? N11 Cu1 O34 C34 -78.81(18) 2_566 . . . ? N11 Cu1 O34 C34 101.19(18) . . . . ? O32 Cu1 O34 C34 -167.60(18) 2_566 . . . ? O32 Cu1 O34 C34 12.40(18) . . . . ? O34 C34 C35 F35C -10.9(4) . . . . ? C33 C34 C35 F35C 170.0(3) . . . . ? O34 C34 C35 F35B 114.6(3) . . . . ? C33 C34 C35 F35B -64.4(3) . . . . ? O34 C34 C35 F35A -132.9(2) . . . . ? C33 C34 C35 F35A 48.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 33.29 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.672 _refine_diff_density_min -1.395 _refine_diff_density_rms 0.094 #END