# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Akiko Hori' 'Miki Hasegawa' 'Takeshi Miyamoto' 'Shohei Takatani' _publ_contact_author_name 'Akiko Hori' _publ_contact_author_email HORI@KITASATO-U.AC.JP _publ_section_title ; Luminescence from pi-pi stacked bipyridines through arene-perfluoroarene interactions ; data_CCDC699205 _database_code_depnum_ccdc_archive 'CCDC 699205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine ; _chemical_name_common 4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine _chemical_melting_point ? _chemical_formula_moiety 'C26 H6 F10 N2' _chemical_formula_sum 'C26 H6 F10 N2' _chemical_formula_weight 536.33 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' _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 5.8933(7) _cell_length_b 7.9383(9) _cell_length_c 11.0988(13) _cell_angle_alpha 88.1100(10) _cell_angle_beta 84.5460(10) _cell_angle_gamma 89.8360(10) _cell_volume 516.60(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100 _cell_measurement_reflns_used 1383 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.34 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9597 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 2730 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.34 _reflns_number_total 2043 _reflns_number_gt 1724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0546P)^2^+0.1458P] 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 2043 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 N1 N 0.7400(2) 0.62020(16) 0.50391(11) 0.0211(3) Uani 1 1 d . . . C1 C 0.9303(2) 0.55336(17) 0.54332(12) 0.0173(3) Uani 1 1 d . . . C2 C 0.9979(2) 0.58045(18) 0.65793(12) 0.0183(3) Uani 1 1 d . . . H2 H 1.1356 0.5332 0.6819 0.022 Uiso 1 1 calc R . . C3 C 0.8590(2) 0.67859(18) 0.73692(13) 0.0189(3) Uani 1 1 d . . . C4 C 0.6584(3) 0.74515(19) 0.69752(13) 0.0226(3) Uani 1 1 d . . . H4 H 0.5583 0.8106 0.7494 0.027 Uiso 1 1 calc R . . C5 C 0.6087(3) 0.7132(2) 0.58044(14) 0.0244(3) Uani 1 1 d . . . H5 H 0.4734 0.7603 0.5534 0.029 Uiso 1 1 calc R . . C6 C 0.9213(2) 0.71111(18) 0.85595(13) 0.0200(3) Uani 1 1 d . . . C7 C 0.9704(2) 0.74064(18) 0.95499(13) 0.0197(3) Uani 1 1 d . . . C8 C 1.0212(2) 0.77842(17) 1.07414(13) 0.0181(3) Uani 1 1 d . . . C9 C 1.2207(2) 0.72265(18) 1.12107(13) 0.0190(3) Uani 1 1 d . . . C10 C 1.2664(2) 0.75766(18) 1.23737(13) 0.0195(3) Uani 1 1 d . . . C11 C 1.1132(2) 0.85065(18) 1.30978(12) 0.0195(3) Uani 1 1 d . . . C12 C 0.9151(2) 0.90856(18) 1.26626(13) 0.0190(3) Uani 1 1 d . . . C13 C 0.8713(2) 0.87311(18) 1.14985(13) 0.0180(3) Uani 1 1 d . . . F1 F 1.37140(15) 0.63267(11) 1.05272(8) 0.0275(2) Uani 1 1 d . . . F2 F 1.45550(14) 0.69882(11) 1.28156(8) 0.0271(2) Uani 1 1 d . . . F3 F 1.15702(15) 0.88411(11) 1.42247(7) 0.0264(2) Uani 1 1 d . . . F4 F 0.76690(15) 0.99980(11) 1.33617(8) 0.0268(2) Uani 1 1 d . . . F5 F 0.68008(14) 0.93439(11) 1.10830(8) 0.0236(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 N1 0.0220(6) 0.0245(7) 0.0173(6) -0.0027(5) -0.0051(5) 0.0020(5) C1 0.0190(7) 0.0170(7) 0.0160(7) -0.0004(5) -0.0025(5) -0.0025(6) C2 0.0197(7) 0.0187(7) 0.0167(7) -0.0001(5) -0.0033(5) -0.0011(5) C3 0.0249(7) 0.0169(7) 0.0152(7) -0.0009(5) -0.0024(5) -0.0039(5) C4 0.0244(8) 0.0238(8) 0.0199(7) -0.0047(6) -0.0011(6) 0.0031(6) C5 0.0229(7) 0.0277(8) 0.0235(8) -0.0040(6) -0.0058(6) 0.0055(6) C6 0.0227(7) 0.0183(7) 0.0190(7) -0.0025(5) -0.0011(6) -0.0004(6) C7 0.0229(7) 0.0179(7) 0.0181(7) -0.0017(5) -0.0010(6) -0.0015(5) C8 0.0212(7) 0.0177(7) 0.0153(7) -0.0016(5) -0.0011(5) -0.0038(5) C9 0.0199(7) 0.0175(7) 0.0191(7) -0.0025(5) 0.0020(5) 0.0007(5) C10 0.0171(7) 0.0197(7) 0.0222(7) 0.0028(6) -0.0056(6) -0.0011(5) C11 0.0257(8) 0.0202(7) 0.0134(7) 0.0005(5) -0.0053(6) -0.0053(6) C12 0.0221(7) 0.0176(7) 0.0170(7) -0.0034(5) 0.0000(6) 0.0013(6) C13 0.0177(7) 0.0189(7) 0.0179(7) 0.0002(5) -0.0043(5) -0.0001(5) F1 0.0248(5) 0.0296(5) 0.0277(5) -0.0077(4) 0.0022(4) 0.0077(4) F2 0.0210(5) 0.0332(5) 0.0282(5) 0.0029(4) -0.0098(4) 0.0033(4) F3 0.0340(5) 0.0320(5) 0.0147(4) -0.0036(4) -0.0088(4) -0.0026(4) F4 0.0296(5) 0.0306(5) 0.0202(5) -0.0086(4) -0.0002(4) 0.0086(4) F5 0.0199(4) 0.0294(5) 0.0224(5) -0.0012(4) -0.0068(3) 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 N1 C5 1.334(2) . ? N1 C1 1.3433(19) . ? C1 C2 1.392(2) . ? C1 C1 1.489(3) 2_766 ? C2 C3 1.397(2) . ? C2 H2 0.9500 . ? C3 C4 1.396(2) . ? C3 C6 1.436(2) . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.194(2) . ? C7 C8 1.4248(19) . ? C8 C13 1.396(2) . ? C8 C9 1.396(2) . ? C9 F1 1.3334(16) . ? C9 C10 1.380(2) . ? C10 F2 1.3367(16) . ? C10 C11 1.380(2) . ? C11 F3 1.3362(15) . ? C11 C12 1.377(2) . ? C12 F4 1.3395(16) . ? C12 C13 1.379(2) . ? C13 F5 1.3419(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 C5 N1 C1 117.61(13) . . ? N1 C1 C2 123.13(13) . . ? N1 C1 C1 116.17(15) . 2_766 ? C2 C1 C1 120.69(16) . 2_766 ? C1 C2 C3 118.58(13) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.56(13) . . ? C4 C3 C6 120.59(13) . . ? C2 C3 C6 120.85(13) . . ? C5 C4 C3 118.30(13) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 123.80(14) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C7 C6 C3 178.79(16) . . ? C6 C7 C8 177.97(16) . . ? C13 C8 C9 116.82(13) . . ? C13 C8 C7 121.07(13) . . ? C9 C8 C7 122.11(13) . . ? F1 C9 C10 118.79(12) . . ? F1 C9 C8 119.61(13) . . ? C10 C9 C8 121.60(13) . . ? F2 C10 C11 119.59(13) . . ? F2 C10 C9 120.53(13) . . ? C11 C10 C9 119.86(13) . . ? F3 C11 C12 120.00(13) . . ? F3 C11 C10 119.86(13) . . ? C12 C11 C10 120.14(13) . . ? F4 C12 C11 120.22(12) . . ? F4 C12 C13 120.25(13) . . ? C11 C12 C13 119.53(13) . . ? F5 C13 C12 118.51(13) . . ? F5 C13 C8 119.44(12) . . ? C12 C13 C8 122.04(13) . . ? 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 C5 N1 C1 C2 -1.7(2) . . . . ? C5 N1 C1 C1 178.47(15) . . . 2_766 ? N1 C1 C2 C3 1.5(2) . . . . ? C1 C1 C2 C3 -178.67(15) 2_766 . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C1 C2 C3 C6 -179.71(13) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C6 C3 C4 C5 178.50(14) . . . . ? C1 N1 C5 C4 0.4(2) . . . . ? C3 C4 C5 N1 1.1(2) . . . . ? C4 C3 C6 C7 -19(8) . . . . ? C2 C3 C6 C7 160(8) . . . . ? C3 C6 C7 C8 29(11) . . . . ? C6 C7 C8 C13 -7(4) . . . . ? C6 C7 C8 C9 173(4) . . . . ? C13 C8 C9 F1 -179.50(12) . . . . ? C7 C8 C9 F1 0.8(2) . . . . ? C13 C8 C9 C10 0.8(2) . . . . ? C7 C8 C9 C10 -178.91(13) . . . . ? F1 C9 C10 F2 -1.6(2) . . . . ? C8 C9 C10 F2 178.07(12) . . . . ? F1 C9 C10 C11 179.94(12) . . . . ? C8 C9 C10 C11 -0.4(2) . . . . ? F2 C10 C11 F3 1.4(2) . . . . ? C9 C10 C11 F3 179.80(12) . . . . ? F2 C10 C11 C12 -178.45(12) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? F3 C11 C12 F4 0.6(2) . . . . ? C10 C11 C12 F4 -179.56(12) . . . . ? F3 C11 C12 C13 -179.90(12) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? F4 C12 C13 F5 1.1(2) . . . . ? C11 C12 C13 F5 -178.34(12) . . . . ? F4 C12 C13 C8 -179.95(12) . . . . ? C11 C12 C13 C8 0.6(2) . . . . ? C9 C8 C13 F5 178.00(12) . . . . ? C7 C8 C13 F5 -2.3(2) . . . . ? C9 C8 C13 C12 -0.9(2) . . . . ? C7 C8 C13 C12 178.80(13) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.232 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.070 # Attachment 'B818880G_CCDC699206.cif' data_CCDC699206 _database_code_depnum_ccdc_archive 'CCDC 699206' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-diphenylethnyl-2,2'-bipyridine, 4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine, benzene ; _chemical_name_common ; 4,4'-diphenylethnyl-2,2'-bipyridine, 4,4'- bis(pentafluorophenylethnyl)-2,2'-bipyridine, benzene ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H6 F10 N2, C26 H16 N2, 0.5(C6 H6)' _chemical_formula_sum 'C55 H25 F10 N4' _chemical_formula_weight 931.79 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' _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 7.463(2) _cell_length_b 15.200(5) _cell_length_c 18.460(6) _cell_angle_alpha 95.369(4) _cell_angle_beta 90.520(4) _cell_angle_gamma 92.737(4) _cell_volume 2082.3(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2369 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 26.31 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 946 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 11010 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.38 _reflns_number_total 8261 _reflns_number_gt 5067 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0726P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8261 _refine_ls_number_parameters 622 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1435 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 N2 N 0.6087(3) 1.07738(13) 0.06877(11) 0.0220(5) Uani 1 1 d . . . N1 N 0.1141(3) 1.07681(13) 0.06739(11) 0.0221(5) Uani 1 1 d . . . N3 N -0.1176(3) 0.40296(13) -0.04464(10) 0.0211(5) Uani 1 1 d . . . N4 N 0.3951(3) 0.40067(13) -0.04593(10) 0.0197(5) Uani 1 1 d . . . C15 C 0.5119(3) 0.92509(16) 0.07518(13) 0.0208(6) Uani 1 1 d . . . H15 H 0.4586 0.8719 0.0515 0.025 Uiso 1 1 calc R . . C14 C 0.5319(3) 0.99997(16) 0.03845(13) 0.0205(5) Uani 1 1 d . . . C1 C 0.0332(3) 1.00064(16) 0.03824(13) 0.0208(5) Uani 1 1 d . . . C13 C 0.0582(3) 0.72370(16) 0.33946(13) 0.0223(6) Uani 1 1 d . . . C22 C 0.4339(3) 0.63343(16) 0.22919(14) 0.0243(6) Uani 1 1 d . . . H22 H 0.4044 0.6277 0.1788 0.029 Uiso 1 1 calc R . . C8 C 0.0036(3) 0.71998(16) 0.26674(13) 0.0212(6) Uani 1 1 d . . . C4 C 0.1590(3) 1.00860(16) 0.17821(14) 0.0238(6) Uani 1 1 d . . . H4 H 0.2046 1.0138 0.2267 0.029 Uiso 1 1 calc R . . C5 C 0.1750(3) 1.07906(17) 0.13607(14) 0.0242(6) Uani 1 1 d . . . H5 H 0.2328 1.1325 0.1572 0.029 Uiso 1 1 calc R . . C9 C -0.0790(3) 0.64037(16) 0.23704(13) 0.0210(6) Uani 1 1 d . . . C24 C 0.4507(3) 0.57011(17) 0.34311(14) 0.0267(6) Uani 1 1 d . . . H24 H 0.4313 0.5208 0.3705 0.032 Uiso 1 1 calc R . . C26 C 0.5492(3) 0.72120(17) 0.33685(14) 0.0251(6) Uani 1 1 d . . . H26 H 0.5992 0.7755 0.3598 0.030 Uiso 1 1 calc R . . C16 C 0.5706(3) 0.92821(16) 0.14740(13) 0.0212(6) Uani 1 1 d . . . C11 C -0.0545(3) 0.57629(16) 0.34895(13) 0.0215(6) Uani 1 1 d . . . C18 C 0.6654(3) 1.07897(16) 0.13816(14) 0.0241(6) Uani 1 1 d . . . H18 H 0.7206 1.1325 0.1604 0.029 Uiso 1 1 calc R . . C23 C 0.4080(3) 0.56242(16) 0.26939(14) 0.0256(6) Uani 1 1 d . . . H23 H 0.3604 0.5076 0.2465 0.031 Uiso 1 1 calc R . . C19 C 0.5484(3) 0.85258(16) 0.18757(14) 0.0229(6) Uani 1 1 d . . . C7 C 0.0304(3) 0.79346(17) 0.22500(13) 0.0226(6) Uani 1 1 d . . . C25 C 0.5216(3) 0.64962(17) 0.37677(14) 0.0266(6) Uani 1 1 d . . . H25 H 0.5511 0.6548 0.4272 0.032 Uiso 1 1 calc R . . C2 C 0.0117(3) 0.92589(16) 0.07582(13) 0.0216(6) Uani 1 1 d . . . H2 H -0.0447 0.8730 0.0530 0.026 Uiso 1 1 calc R . . C12 C 0.0310(3) 0.65337(17) 0.37985(13) 0.0217(6) Uani 1 1 d . . . C17 C 0.6486(3) 1.00773(16) 0.17923(14) 0.0238(6) Uani 1 1 d . . . H17 H 0.6896 1.0129 0.2284 0.029 Uiso 1 1 calc R . . C6 C 0.0512(3) 0.85498(17) 0.18939(13) 0.0237(6) Uani 1 1 d . . . C3 C 0.0742(3) 0.92956(16) 0.14771(13) 0.0210(6) Uani 1 1 d . . . C21 C 0.5041(3) 0.71444(16) 0.26284(13) 0.0222(6) Uani 1 1 d . . . C10 C -0.1072(3) 0.56945(16) 0.27688(13) 0.0213(5) Uani 1 1 d . . . C20 C 0.5294(3) 0.78946(17) 0.22187(13) 0.0235(6) Uani 1 1 d . . . C47 C 0.5409(3) 0.27328(16) 0.29548(12) 0.0189(5) Uani 1 1 d . . . C48 C 0.6176(3) 0.33935(16) 0.34519(13) 0.0215(6) Uani 1 1 d . . . H48 H 0.6448 0.3966 0.3304 0.026 Uiso 1 1 calc R . . C49 C 0.6544(3) 0.32221(17) 0.41598(13) 0.0247(6) Uani 1 1 d . . . H49 H 0.7056 0.3677 0.4497 0.030 Uiso 1 1 calc R . . C51 C 0.5413(3) 0.17222(17) 0.38851(14) 0.0258(6) Uani 1 1 d . . . H51 H 0.5154 0.1149 0.4035 0.031 Uiso 1 1 calc R . . C27 C -0.0318(3) 0.45492(15) 0.00875(13) 0.0194(5) Uani 1 1 d . . . C50 C 0.6163(3) 0.23849(17) 0.43754(13) 0.0252(6) Uani 1 1 d . . . H50 H 0.6419 0.2266 0.4861 0.030 Uiso 1 1 calc R . . C40 C 0.4712(3) 0.45473(15) 0.00861(13) 0.0177(5) Uani 1 1 d . . . C52 C 0.5037(3) 0.18905(16) 0.31768(13) 0.0214(6) Uani 1 1 d . . . H52 H 0.4525 0.1433 0.2842 0.026 Uiso 1 1 calc R . . C41 C 0.4974(3) 0.42867(15) 0.07817(12) 0.0183(5) Uani 1 1 d . . . H41 H 0.5518 0.4686 0.1155 0.022 Uiso 1 1 calc R . . C31 C -0.1707(3) 0.32116(16) -0.03035(13) 0.0220(6) Uani 1 1 d . . . H31 H -0.2300 0.2838 -0.0682 0.026 Uiso 1 1 calc R . . C43 C 0.3618(3) 0.28696(16) 0.03562(13) 0.0192(5) Uani 1 1 d . . . H43 H 0.3215 0.2283 0.0432 0.023 Uiso 1 1 calc R . . C46 C 0.5016(3) 0.29326(16) 0.22265(13) 0.0205(5) Uani 1 1 d . . . C45 C 0.4720(3) 0.31428(15) 0.16286(13) 0.0197(5) Uani 1 1 d . . . C29 C -0.0579(3) 0.34175(16) 0.09142(13) 0.0197(5) Uani 1 1 d . . . C34 C 0.0429(3) 0.27104(16) 0.29414(13) 0.0192(5) Uani 1 1 d . . . C33 C 0.0021(3) 0.29011(16) 0.22162(13) 0.0214(6) Uani 1 1 d . . . C44 C 0.3418(3) 0.31895(16) -0.03149(13) 0.0203(5) Uani 1 1 d . . . H44 H 0.2868 0.2805 -0.0697 0.024 Uiso 1 1 calc R . . C35 C 0.1284(3) 0.33471(16) 0.34295(13) 0.0215(6) Uani 1 1 d . . . C36 C 0.1694(3) 0.31937(17) 0.41337(13) 0.0231(6) Uani 1 1 d . . . C42 C 0.4425(3) 0.34296(15) 0.09193(12) 0.0176(5) Uani 1 1 d . . . C39 C -0.0012(3) 0.18968(16) 0.32040(13) 0.0204(5) Uani 1 1 d . . . C30 C -0.1450(3) 0.28735(16) 0.03571(13) 0.0225(6) Uani 1 1 d . . . H30 H -0.1856 0.2287 0.0429 0.027 Uiso 1 1 calc R . . C38 C 0.0405(3) 0.17283(16) 0.39011(13) 0.0237(6) Uani 1 1 d . . . C28 C 0.0002(3) 0.42716(16) 0.07741(13) 0.0213(6) Uani 1 1 d . . . H28 H 0.0606 0.4658 0.1141 0.026 Uiso 1 1 calc R . . C32 C -0.0263(3) 0.31227(16) 0.16223(14) 0.0211(6) Uani 1 1 d . . . C37 C 0.1267(3) 0.23765(17) 0.43669(13) 0.0238(6) Uani 1 1 d . . . C54 C 0.3232(4) 0.98075(19) 0.47958(18) 0.0414(8) Uani 1 1 d . . . H54 H 0.2014 0.9675 0.4655 0.050 Uiso 1 1 calc R . . C55 C 0.3642(4) 1.03637(19) 0.54115(19) 0.0446(8) Uani 1 1 d . . . H55 H 0.2708 1.0615 0.5696 0.053 Uiso 1 1 calc R . . C53 C 0.4581(4) 0.94420(19) 0.43829(18) 0.0434(8) Uani 1 1 d . . . H53 H 0.4296 0.9057 0.3958 0.052 Uiso 1 1 calc R . . F4 F 0.08652(19) 0.65801(10) 0.44952(7) 0.0324(4) Uani 1 1 d . . . F6 F 0.17538(19) 0.41394(9) 0.32072(8) 0.0291(4) Uani 1 1 d . . . F5 F 0.13812(19) 0.79827(10) 0.37141(8) 0.0324(4) Uani 1 1 d . . . F2 F -0.18709(19) 0.49379(9) 0.24610(8) 0.0304(4) Uani 1 1 d . . . F9 F -0.0023(2) 0.09379(9) 0.41295(8) 0.0340(4) Uani 1 1 d . . . F1 F -0.13580(19) 0.63305(9) 0.16794(7) 0.0287(4) Uani 1 1 d . . . F8 F 0.1697(2) 0.22119(10) 0.50462(7) 0.0343(4) Uani 1 1 d . . . F7 F 0.25057(19) 0.38343(10) 0.45882(8) 0.0329(4) Uani 1 1 d . . . F10 F -0.08571(18) 0.12555(9) 0.27646(7) 0.0275(4) Uani 1 1 d . . . F3 F -0.08714(19) 0.50877(9) 0.38924(8) 0.0317(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 N2 0.0207(11) 0.0185(11) 0.0260(12) -0.0015(9) -0.0022(9) -0.0012(9) N1 0.0211(11) 0.0199(11) 0.0248(12) 0.0002(9) 0.0016(9) 0.0001(9) N3 0.0206(11) 0.0253(12) 0.0179(11) 0.0027(9) -0.0002(9) 0.0041(9) N4 0.0190(11) 0.0240(12) 0.0160(11) 0.0021(9) -0.0025(9) -0.0004(9) C15 0.0161(13) 0.0185(13) 0.0273(15) -0.0018(11) 0.0029(11) 0.0005(10) C14 0.0142(12) 0.0213(13) 0.0254(14) -0.0019(11) 0.0023(11) 0.0021(10) C1 0.0178(13) 0.0200(13) 0.0248(14) 0.0014(11) 0.0042(11) 0.0029(10) C13 0.0191(13) 0.0218(14) 0.0248(14) -0.0033(11) -0.0018(11) -0.0012(10) C22 0.0242(14) 0.0277(15) 0.0203(14) -0.0002(11) 0.0012(11) -0.0017(11) C8 0.0152(13) 0.0242(14) 0.0245(14) 0.0031(11) 0.0019(11) 0.0030(10) C4 0.0187(13) 0.0280(15) 0.0245(14) 0.0000(11) 0.0010(11) 0.0032(11) C5 0.0219(14) 0.0240(14) 0.0259(15) -0.0011(11) 0.0009(11) -0.0010(11) C9 0.0182(13) 0.0292(15) 0.0152(13) -0.0002(11) 0.0002(10) 0.0035(10) C24 0.0263(14) 0.0230(14) 0.0319(16) 0.0077(12) 0.0048(12) 0.0019(11) C26 0.0225(14) 0.0247(14) 0.0270(15) -0.0030(12) -0.0001(11) 0.0005(11) C16 0.0153(13) 0.0212(13) 0.0269(15) 0.0007(11) 0.0028(11) 0.0012(10) C11 0.0215(13) 0.0237(14) 0.0212(14) 0.0087(11) 0.0038(11) 0.0058(11) C18 0.0228(14) 0.0207(14) 0.0271(15) -0.0042(11) -0.0014(11) -0.0026(11) C23 0.0278(14) 0.0207(14) 0.0271(15) -0.0016(11) 0.0034(12) -0.0035(11) C19 0.0181(13) 0.0230(14) 0.0263(15) -0.0036(12) -0.0020(11) -0.0004(10) C7 0.0212(14) 0.0258(15) 0.0205(14) 0.0015(12) 0.0010(11) 0.0005(11) C25 0.0229(14) 0.0359(16) 0.0209(14) -0.0001(12) -0.0014(11) 0.0044(12) C2 0.0182(13) 0.0191(13) 0.0276(15) 0.0024(11) 0.0042(11) 0.0001(10) C12 0.0200(13) 0.0303(15) 0.0146(13) 0.0005(11) -0.0037(10) 0.0034(11) C17 0.0205(13) 0.0263(14) 0.0236(14) -0.0017(11) -0.0017(11) -0.0004(11) C6 0.0187(13) 0.0308(15) 0.0211(14) -0.0004(12) 0.0012(11) 0.0004(11) C3 0.0162(13) 0.0226(14) 0.0249(14) 0.0042(11) 0.0048(11) 0.0034(10) C21 0.0177(13) 0.0232(14) 0.0258(15) 0.0019(11) 0.0049(11) 0.0021(10) C10 0.0191(13) 0.0190(13) 0.0247(14) -0.0027(10) -0.0005(11) -0.0008(10) C20 0.0200(13) 0.0249(15) 0.0247(15) -0.0030(12) 0.0013(11) 0.0028(11) C47 0.0168(12) 0.0240(14) 0.0170(13) 0.0049(10) 0.0014(10) 0.0056(10) C48 0.0220(13) 0.0193(13) 0.0244(14) 0.0073(11) 0.0012(11) 0.0019(10) C49 0.0266(14) 0.0270(15) 0.0204(14) 0.0015(11) -0.0028(11) 0.0016(11) C51 0.0265(14) 0.0258(15) 0.0268(15) 0.0108(12) 0.0026(12) 0.0030(11) C27 0.0158(12) 0.0238(14) 0.0189(13) 0.0015(11) 0.0028(10) 0.0037(10) C50 0.0246(14) 0.0362(16) 0.0165(13) 0.0096(12) 0.0001(11) 0.0054(12) C40 0.0151(12) 0.0198(13) 0.0182(13) 0.0007(10) 0.0006(10) 0.0033(10) C52 0.0225(13) 0.0195(13) 0.0225(14) 0.0025(11) -0.0010(11) 0.0015(10) C41 0.0184(13) 0.0218(13) 0.0148(13) 0.0016(10) 0.0000(10) 0.0021(10) C31 0.0215(13) 0.0226(14) 0.0213(14) -0.0001(11) 0.0014(11) 0.0011(10) C43 0.0172(12) 0.0178(13) 0.0230(14) 0.0032(10) 0.0004(10) 0.0022(10) C46 0.0176(13) 0.0221(14) 0.0221(14) 0.0038(11) 0.0011(11) -0.0003(10) C45 0.0187(13) 0.0199(13) 0.0207(14) 0.0032(10) 0.0008(11) 0.0014(10) C29 0.0179(13) 0.0215(13) 0.0207(14) 0.0053(10) 0.0033(10) 0.0043(10) C34 0.0167(12) 0.0225(13) 0.0189(13) 0.0037(10) 0.0013(10) 0.0034(10) C33 0.0163(13) 0.0232(14) 0.0253(15) 0.0040(11) 0.0016(11) 0.0020(10) C44 0.0213(13) 0.0203(13) 0.0185(13) -0.0014(10) -0.0021(11) -0.0004(10) C35 0.0211(13) 0.0175(13) 0.0259(14) 0.0036(11) 0.0013(11) -0.0006(10) C36 0.0177(13) 0.0291(15) 0.0211(14) -0.0050(11) -0.0034(11) 0.0018(11) C42 0.0153(12) 0.0230(13) 0.0149(13) 0.0032(10) 0.0002(10) 0.0045(10) C39 0.0162(13) 0.0213(13) 0.0230(14) -0.0008(11) -0.0007(11) 0.0003(10) C30 0.0214(13) 0.0222(14) 0.0242(14) 0.0039(11) 0.0030(11) 0.0008(10) C38 0.0244(14) 0.0232(14) 0.0256(15) 0.0117(11) 0.0050(11) 0.0033(11) C28 0.0185(13) 0.0254(14) 0.0203(14) 0.0029(11) -0.0009(11) 0.0045(10) C32 0.0190(13) 0.0195(13) 0.0249(15) 0.0031(11) 0.0007(11) 0.0006(10) C37 0.0228(14) 0.0340(16) 0.0157(13) 0.0053(11) -0.0018(11) 0.0073(11) C54 0.0309(16) 0.0264(16) 0.070(2) 0.0204(16) -0.0068(16) -0.0017(13) C55 0.0380(18) 0.0242(16) 0.074(2) 0.0159(16) 0.0038(17) 0.0064(13) C53 0.0440(19) 0.0261(16) 0.062(2) 0.0138(15) -0.0052(17) -0.0014(14) F4 0.0339(9) 0.0441(10) 0.0194(8) 0.0034(7) -0.0068(7) 0.0042(7) F6 0.0324(8) 0.0206(8) 0.0345(9) 0.0065(6) 0.0022(7) -0.0045(6) F5 0.0335(9) 0.0303(9) 0.0308(9) -0.0052(7) -0.0062(7) -0.0072(7) F2 0.0350(9) 0.0238(8) 0.0309(9) -0.0027(6) 0.0005(7) -0.0048(7) F9 0.0409(9) 0.0272(9) 0.0362(9) 0.0160(7) 0.0028(7) 0.0011(7) F1 0.0301(8) 0.0385(9) 0.0171(8) 0.0021(6) -0.0034(6) -0.0007(7) F8 0.0404(9) 0.0452(10) 0.0191(8) 0.0078(7) -0.0049(7) 0.0114(8) F7 0.0327(9) 0.0345(9) 0.0290(9) -0.0072(7) -0.0080(7) -0.0020(7) F10 0.0295(8) 0.0242(8) 0.0279(8) -0.0004(6) -0.0016(7) -0.0042(6) F3 0.0397(9) 0.0285(9) 0.0289(9) 0.0122(7) 0.0036(7) 0.0036(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 N2 C18 1.343(3) . ? N2 C14 1.354(3) . ? N1 C5 1.340(3) . ? N1 C1 1.344(3) . ? N3 C31 1.337(3) . ? N3 C27 1.342(3) . ? N4 C44 1.338(3) . ? N4 C40 1.342(3) . ? C15 C14 1.381(3) . ? C15 C16 1.396(3) . ? C15 H15 0.9500 . ? C14 C14 1.493(5) 2_675 ? C1 C2 1.389(3) . ? C1 C1 1.490(5) 2_575 ? C13 F5 1.339(3) . ? C13 C12 1.368(3) . ? C13 C8 1.395(3) . ? C22 C23 1.373(3) . ? C22 C21 1.402(3) . ? C22 H22 0.9500 . ? C8 C9 1.394(3) . ? C8 C7 1.423(3) . ? C4 C5 1.383(3) . ? C4 C3 1.399(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C9 F1 1.334(3) . ? C9 C10 1.370(3) . ? C24 C25 1.385(3) . ? C24 C23 1.388(3) . ? C24 H24 0.9500 . ? C26 C25 1.379(3) . ? C26 C21 1.397(3) . ? C26 H26 0.9500 . ? C16 C17 1.392(3) . ? C16 C19 1.429(4) . ? C11 F3 1.337(3) . ? C11 C10 1.377(3) . ? C11 C12 1.379(3) . ? C18 C17 1.380(3) . ? C18 H18 0.9500 . ? C23 H23 0.9500 . ? C19 C20 1.202(3) . ? C7 C6 1.197(3) . ? C25 H25 0.9500 . ? C2 C3 1.398(3) . ? C2 H2 0.9500 . ? C12 F4 1.342(3) . ? C17 H17 0.9500 . ? C6 C3 1.433(3) . ? C21 C20 1.432(4) . ? C10 F2 1.344(3) . ? C47 C48 1.393(3) . ? C47 C52 1.397(3) . ? C47 C46 1.437(3) . ? C48 C49 1.384(3) . ? C48 H48 0.9500 . ? C49 C50 1.386(3) . ? C49 H49 0.9500 . ? C51 C50 1.383(3) . ? C51 C52 1.384(3) . ? C51 H51 0.9500 . ? C27 C28 1.395(3) . ? C27 C27 1.494(5) 2_565 ? C50 H50 0.9500 . ? C40 C41 1.394(3) . ? C40 C40 1.486(5) 2_665 ? C52 H52 0.9500 . ? C41 C42 1.394(3) . ? C41 H41 0.9500 . ? C31 C30 1.382(3) . ? C31 H31 0.9500 . ? C43 C44 1.382(3) . ? C43 C42 1.394(3) . ? C43 H43 0.9500 . ? C46 C45 1.199(3) . ? C45 C42 1.437(3) . ? C29 C30 1.393(3) . ? C29 C28 1.397(3) . ? C29 C32 1.442(3) . ? C34 C35 1.387(3) . ? C34 C39 1.396(3) . ? C34 C33 1.429(3) . ? C33 C32 1.197(3) . ? C44 H44 0.9500 . ? C35 F6 1.340(3) . ? C35 C36 1.376(3) . ? C36 F7 1.342(3) . ? C36 C37 1.376(4) . ? C39 F10 1.338(3) . ? C39 C38 1.371(3) . ? C30 H30 0.9500 . ? C38 F9 1.336(3) . ? C38 C37 1.377(3) . ? C28 H28 0.9500 . ? C37 F8 1.341(3) . ? C54 C55 1.375(4) . ? C54 C53 1.375(4) . ? C54 H54 0.9500 . ? C55 C53 1.386(4) 2_676 ? C55 H55 0.9500 . ? C53 C55 1.386(4) 2_676 ? C53 H53 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 N2 C14 116.5(2) . . ? C5 N1 C1 117.2(2) . . ? C31 N3 C27 117.4(2) . . ? C44 N4 C40 117.5(2) . . ? C14 C15 C16 119.4(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N2 C14 C15 123.2(2) . . ? N2 C14 C14 115.6(3) . 2_675 ? C15 C14 C14 121.2(3) . 2_675 ? N1 C1 C2 123.1(2) . . ? N1 C1 C1 116.4(3) . 2_575 ? C2 C1 C1 120.6(3) . 2_575 ? F5 C13 C12 118.5(2) . . ? F5 C13 C8 119.5(2) . . ? C12 C13 C8 122.0(2) . . ? C23 C22 C21 119.8(2) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C9 C8 C13 116.4(2) . . ? C9 C8 C7 121.7(2) . . ? C13 C8 C7 121.9(2) . . ? C5 C4 C3 118.4(2) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 124.2(2) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? F1 C9 C10 118.5(2) . . ? F1 C9 C8 119.2(2) . . ? C10 C9 C8 122.2(2) . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C25 C26 C21 120.5(2) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C17 C16 C15 117.8(2) . . ? C17 C16 C19 121.3(2) . . ? C15 C16 C19 120.9(2) . . ? F3 C11 C10 120.3(2) . . ? F3 C11 C12 119.9(2) . . ? C10 C11 C12 119.9(2) . . ? N2 C18 C17 124.1(2) . . ? N2 C18 H18 117.9 . . ? C17 C18 H18 117.9 . . ? C22 C23 C24 120.6(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C20 C19 C16 179.4(3) . . ? C6 C7 C8 179.2(3) . . ? C26 C25 C24 119.8(2) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? F4 C12 C13 121.0(2) . . ? F4 C12 C11 119.1(2) . . ? C13 C12 C11 119.9(2) . . ? C18 C17 C16 118.9(2) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C7 C6 C3 179.0(3) . . ? C2 C3 C4 118.0(2) . . ? C2 C3 C6 121.2(2) . . ? C4 C3 C6 120.7(2) . . ? C26 C21 C22 119.3(2) . . ? C26 C21 C20 120.3(2) . . ? C22 C21 C20 120.4(2) . . ? F2 C10 C9 120.3(2) . . ? F2 C10 C11 120.1(2) . . ? C9 C10 C11 119.6(2) . . ? C19 C20 C21 179.2(3) . . ? C48 C47 C52 119.2(2) . . ? C48 C47 C46 119.4(2) . . ? C52 C47 C46 121.5(2) . . ? C49 C48 C47 120.5(2) . . ? C49 C48 H48 119.7 . . ? C47 C48 H48 119.7 . . ? C48 C49 C50 119.8(2) . . ? C48 C49 H49 120.1 . . ? C50 C49 H49 120.1 . . ? C50 C51 C52 120.3(2) . . ? C50 C51 H51 119.9 . . ? C52 C51 H51 119.9 . . ? N3 C27 C28 122.6(2) . . ? N3 C27 C27 116.8(3) . 2_565 ? C28 C27 C27 120.6(3) . 2_565 ? C51 C50 C49 120.1(2) . . ? C51 C50 H50 119.9 . . ? C49 C50 H50 119.9 . . ? N4 C40 C41 122.7(2) . . ? N4 C40 C40 116.6(3) . 2_665 ? C41 C40 C40 120.6(3) . 2_665 ? C51 C52 C47 120.0(2) . . ? C51 C52 H52 120.0 . . ? C47 C52 H52 120.0 . . ? C40 C41 C42 118.8(2) . . ? C40 C41 H41 120.6 . . ? C42 C41 H41 120.6 . . ? N3 C31 C30 124.4(2) . . ? N3 C31 H31 117.8 . . ? C30 C31 H31 117.8 . . ? C44 C43 C42 118.3(2) . . ? C44 C43 H43 120.9 . . ? C42 C43 H43 120.9 . . ? C45 C46 C47 176.7(3) . . ? C46 C45 C42 177.3(3) . . ? C30 C29 C28 118.4(2) . . ? C30 C29 C32 122.0(2) . . ? C28 C29 C32 119.7(2) . . ? C35 C34 C39 116.3(2) . . ? C35 C34 C33 120.6(2) . . ? C39 C34 C33 123.2(2) . . ? C32 C33 C34 175.1(3) . . ? N4 C44 C43 124.0(2) . . ? N4 C44 H44 118.0 . . ? C43 C44 H44 118.0 . . ? F6 C35 C36 118.5(2) . . ? F6 C35 C34 119.0(2) . . ? C36 C35 C34 122.5(2) . . ? F7 C36 C35 120.3(2) . . ? F7 C36 C37 120.3(2) . . ? C35 C36 C37 119.4(2) . . ? C43 C42 C41 118.6(2) . . ? C43 C42 C45 121.8(2) . . ? C41 C42 C45 119.6(2) . . ? F10 C39 C38 118.5(2) . . ? F10 C39 C34 119.4(2) . . ? C38 C39 C34 122.1(2) . . ? C31 C30 C29 118.1(2) . . ? C31 C30 H30 120.9 . . ? C29 C30 H30 120.9 . . ? F9 C38 C39 120.2(2) . . ? F9 C38 C37 119.9(2) . . ? C39 C38 C37 119.8(2) . . ? C27 C28 C29 119.1(2) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? C33 C32 C29 178.1(3) . . ? F8 C37 C36 120.0(2) . . ? F8 C37 C38 120.1(2) . . ? C36 C37 C38 119.9(2) . . ? C55 C54 C53 120.1(3) . . ? C55 C54 H54 119.9 . . ? C53 C54 H54 119.9 . . ? C54 C55 C53 120.0(3) . 2_676 ? C54 C55 H55 120.0 . . ? C53 C55 H55 120.0 2_676 . ? C54 C53 C55 119.9(3) . 2_676 ? C54 C53 H53 120.1 . . ? C55 C53 H53 120.1 2_676 . ? 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 C18 N2 C14 C15 -0.4(3) . . . . ? C18 N2 C14 C14 179.4(2) . . . 2_675 ? C16 C15 C14 N2 0.9(4) . . . . ? C16 C15 C14 C14 -179.0(3) . . . 2_675 ? C5 N1 C1 C2 -0.3(4) . . . . ? C5 N1 C1 C1 -179.8(3) . . . 2_575 ? F5 C13 C8 C9 -179.9(2) . . . . ? C12 C13 C8 C9 -0.5(4) . . . . ? F5 C13 C8 C7 0.0(4) . . . . ? C12 C13 C8 C7 179.4(2) . . . . ? C1 N1 C5 C4 -0.2(4) . . . . ? C3 C4 C5 N1 0.0(4) . . . . ? C13 C8 C9 F1 179.3(2) . . . . ? C7 C8 C9 F1 -0.6(4) . . . . ? C13 C8 C9 C10 0.6(4) . . . . ? C7 C8 C9 C10 -179.3(2) . . . . ? C14 C15 C16 C17 -0.4(3) . . . . ? C14 C15 C16 C19 178.6(2) . . . . ? C14 N2 C18 C17 -0.5(4) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C25 C24 C23 C22 -0.6(4) . . . . ? C17 C16 C19 C20 34(29) . . . . ? C15 C16 C19 C20 -144(28) . . . . ? C9 C8 C7 C6 30(24) . . . . ? C13 C8 C7 C6 -150(23) . . . . ? C21 C26 C25 C24 0.8(4) . . . . ? C23 C24 C25 C26 0.2(4) . . . . ? N1 C1 C2 C3 1.0(4) . . . . ? C1 C1 C2 C3 -179.5(3) 2_575 . . . ? F5 C13 C12 F4 -1.4(4) . . . . ? C8 C13 C12 F4 179.2(2) . . . . ? F5 C13 C12 C11 178.6(2) . . . . ? C8 C13 C12 C11 -0.8(4) . . . . ? F3 C11 C12 F4 2.6(3) . . . . ? C10 C11 C12 F4 -178.0(2) . . . . ? F3 C11 C12 C13 -177.4(2) . . . . ? C10 C11 C12 C13 2.0(4) . . . . ? N2 C18 C17 C16 1.0(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C19 C16 C17 C18 -179.4(2) . . . . ? C8 C7 C6 C3 92(29) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C1 C2 C3 C6 178.4(2) . . . . ? C5 C4 C3 C2 0.7(3) . . . . ? C5 C4 C3 C6 -178.9(2) . . . . ? C7 C6 C3 C2 -120(16) . . . . ? C7 C6 C3 C4 59(16) . . . . ? C25 C26 C21 C22 -1.3(4) . . . . ? C25 C26 C21 C20 178.7(2) . . . . ? C23 C22 C21 C26 0.9(4) . . . . ? C23 C22 C21 C20 -179.1(2) . . . . ? F1 C9 C10 F2 1.4(3) . . . . ? C8 C9 C10 F2 -179.9(2) . . . . ? F1 C9 C10 C11 -178.1(2) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? F3 C11 C10 F2 -2.0(4) . . . . ? C12 C11 C10 F2 178.6(2) . . . . ? F3 C11 C10 C9 177.5(2) . . . . ? C12 C11 C10 C9 -1.9(4) . . . . ? C16 C19 C20 C21 70(38) . . . . ? C26 C21 C20 C19 -100(19) . . . . ? C22 C21 C20 C19 80(19) . . . . ? C52 C47 C48 C49 -0.8(4) . . . . ? C46 C47 C48 C49 179.0(2) . . . . ? C47 C48 C49 C50 0.6(4) . . . . ? C31 N3 C27 C28 -1.1(3) . . . . ? C31 N3 C27 C27 178.1(2) . . . 2_565 ? C52 C51 C50 C49 0.0(4) . . . . ? C48 C49 C50 C51 -0.2(4) . . . . ? C44 N4 C40 C41 0.7(3) . . . . ? C44 N4 C40 C40 -179.8(2) . . . 2_665 ? C50 C51 C52 C47 -0.2(4) . . . . ? C48 C47 C52 C51 0.6(4) . . . . ? C46 C47 C52 C51 -179.2(2) . . . . ? N4 C40 C41 C42 0.0(4) . . . . ? C40 C40 C41 C42 -179.6(3) 2_665 . . . ? C27 N3 C31 C30 0.9(4) . . . . ? C48 C47 C46 C45 -1(5) . . . . ? C52 C47 C46 C45 179(100) . . . . ? C47 C46 C45 C42 20(9) . . . . ? C35 C34 C33 C32 0(3) . . . . ? C39 C34 C33 C32 180(100) . . . . ? C40 N4 C44 C43 -0.6(4) . . . . ? C42 C43 C44 N4 0.0(4) . . . . ? C39 C34 C35 F6 179.5(2) . . . . ? C33 C34 C35 F6 -1.2(4) . . . . ? C39 C34 C35 C36 0.3(4) . . . . ? C33 C34 C35 C36 179.6(2) . . . . ? F6 C35 C36 F7 1.6(4) . . . . ? C34 C35 C36 F7 -179.3(2) . . . . ? F6 C35 C36 C37 -178.2(2) . . . . ? C34 C35 C36 C37 0.9(4) . . . . ? C44 C43 C42 C41 0.7(3) . . . . ? C44 C43 C42 C45 -178.6(2) . . . . ? C40 C41 C42 C43 -0.6(3) . . . . ? C40 C41 C42 C45 178.6(2) . . . . ? C46 C45 C42 C43 163(6) . . . . ? C46 C45 C42 C41 -16(6) . . . . ? C35 C34 C39 F10 179.3(2) . . . . ? C33 C34 C39 F10 0.0(4) . . . . ? C35 C34 C39 C38 -1.1(4) . . . . ? C33 C34 C39 C38 179.6(2) . . . . ? N3 C31 C30 C29 -0.1(4) . . . . ? C28 C29 C30 C31 -0.6(3) . . . . ? C32 C29 C30 C31 179.6(2) . . . . ? F10 C39 C38 F9 0.3(3) . . . . ? C34 C39 C38 F9 -179.3(2) . . . . ? F10 C39 C38 C37 -179.7(2) . . . . ? C34 C39 C38 C37 0.7(4) . . . . ? N3 C27 C28 C29 0.5(4) . . . . ? C27 C27 C28 C29 -178.7(3) 2_565 . . . ? C30 C29 C28 C27 0.4(3) . . . . ? C32 C29 C28 C27 -179.8(2) . . . . ? C34 C33 C32 C29 -1(11) . . . . ? C30 C29 C32 C33 -178(100) . . . . ? C28 C29 C32 C33 2(9) . . . . ? F7 C36 C37 F8 -1.4(4) . . . . ? C35 C36 C37 F8 178.4(2) . . . . ? F7 C36 C37 C38 178.8(2) . . . . ? C35 C36 C37 C38 -1.3(4) . . . . ? F9 C38 C37 F8 0.8(4) . . . . ? C39 C38 C37 F8 -179.2(2) . . . . ? F9 C38 C37 C36 -179.4(2) . . . . ? C39 C38 C37 C36 0.6(4) . . . . ? C53 C54 C55 C53 0.1(5) . . . 2_676 ? C55 C54 C53 C55 -0.1(5) . . . 2_676 ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.323 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.066 # Attachment 'B818880G_CCDC699207.cif' data_CCDC699207 _database_code_depnum_ccdc_archive 'CCDC 699207' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-diphenylethnyl-2,2'-bipyridine, hexafluorobenzene ; _chemical_formula_moiety 'C26 H16 N2, C6 F6' _chemical_formula_sum 'C32 H16 F6 N2' _chemical_formula_weight 542.47 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7927(12) _cell_length_b 11.3308(13) _cell_length_c 10.4449(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.4640(10) _cell_angle_gamma 90.00 _cell_volume 1218.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2497 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 6635 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.94 _reflns_number_total 2778 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0551P)^2^+0.3980P] 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 2778 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 N1 N 0.53983(12) 0.15366(11) 0.03398(12) 0.0207(3) Uani 1 1 d . . . C1 C 0.52761(13) 0.03873(12) 0.05933(13) 0.0171(3) Uani 1 1 d . . . C2 C 0.56307(13) -0.00792(12) 0.18872(13) 0.0175(3) Uani 1 1 d . . . H2 H 0.5524 -0.0897 0.2024 0.021 Uiso 1 1 calc R . . C3 C 0.61437(13) 0.06688(13) 0.29785(14) 0.0174(3) Uani 1 1 d . . . C4 C 0.62615(14) 0.18694(13) 0.27231(14) 0.0204(3) Uani 1 1 d . . . H4 H 0.6596 0.2412 0.3437 0.024 Uiso 1 1 calc R . . C5 C 0.58758(15) 0.22452(13) 0.13991(15) 0.0223(3) Uani 1 1 d . . . H5 H 0.5956 0.3062 0.1232 0.027 Uiso 1 1 calc R . . C6 C 0.65329(14) 0.02209(12) 0.43273(14) 0.0182(3) Uani 1 1 d . . . C7 C 0.68662(14) -0.01398(12) 0.54583(14) 0.0184(3) Uani 1 1 d . . . C8 C 0.72465(13) -0.05209(13) 0.68326(14) 0.0174(3) Uani 1 1 d . . . C9 C 0.69476(14) -0.16581(13) 0.71751(15) 0.0211(3) Uani 1 1 d . . . H9 H 0.6512 -0.2199 0.6493 0.025 Uiso 1 1 calc R . . C10 C 0.72908(15) -0.19916(14) 0.85141(15) 0.0247(3) Uani 1 1 d . . . H10 H 0.7088 -0.2763 0.8747 0.030 Uiso 1 1 calc R . . C11 C 0.79286(15) -0.12057(15) 0.95162(15) 0.0255(3) Uani 1 1 d . . . H11 H 0.8155 -0.1439 1.0431 0.031 Uiso 1 1 calc R . . C12 C 0.82343(15) -0.00827(14) 0.91832(15) 0.0240(3) Uani 1 1 d . . . H12 H 0.8674 0.0452 0.9870 0.029 Uiso 1 1 calc R . . C13 C 0.79009(14) 0.02640(13) 0.78513(14) 0.0198(3) Uani 1 1 d . . . H13 H 0.8115 0.1034 0.7627 0.024 Uiso 1 1 calc R . . C14 C 0.95659(15) 0.46388(16) 0.86809(15) 0.0266(4) Uani 1 1 d . . . C15 C 0.97032(15) 0.38282(15) 0.96984(16) 0.0269(4) Uani 1 1 d . . . C16 C 1.01398(15) 0.41915(15) 1.10205(16) 0.0269(4) Uani 1 1 d . . . F1 F 0.91364(10) 0.42879(10) 0.73991(9) 0.0396(3) Uani 1 1 d . . . F2 F 0.93963(10) 0.26980(9) 0.94048(11) 0.0401(3) Uani 1 1 d . . . F3 F 1.02636(10) 0.34059(10) 1.20070(10) 0.0379(3) 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 N1 0.0271(7) 0.0175(6) 0.0166(6) 0.0005(5) 0.0049(5) -0.0027(5) C1 0.0187(7) 0.0170(7) 0.0153(7) 0.0007(5) 0.0048(5) 0.0001(5) C2 0.0212(7) 0.0149(7) 0.0162(7) 0.0008(5) 0.0055(5) 0.0003(5) C3 0.0190(7) 0.0191(7) 0.0143(7) 0.0005(5) 0.0051(5) 0.0007(5) C4 0.0243(7) 0.0182(7) 0.0177(7) -0.0028(6) 0.0049(6) -0.0039(6) C5 0.0304(8) 0.0151(7) 0.0200(8) -0.0002(6) 0.0058(6) -0.0045(6) C6 0.0215(7) 0.0167(7) 0.0158(7) -0.0027(5) 0.0046(5) -0.0012(6) C7 0.0210(7) 0.0161(7) 0.0175(7) -0.0027(5) 0.0051(5) -0.0008(5) C8 0.0189(7) 0.0190(7) 0.0140(7) 0.0003(5) 0.0047(5) 0.0026(6) C9 0.0243(7) 0.0184(7) 0.0190(7) -0.0008(6) 0.0040(6) -0.0003(6) C10 0.0293(8) 0.0212(7) 0.0239(8) 0.0066(6) 0.0081(6) 0.0010(6) C11 0.0263(8) 0.0328(9) 0.0158(7) 0.0053(6) 0.0039(6) 0.0031(7) C12 0.0239(8) 0.0296(8) 0.0162(7) -0.0029(6) 0.0025(6) -0.0019(6) C13 0.0235(7) 0.0184(7) 0.0173(7) -0.0004(6) 0.0058(6) -0.0011(6) C14 0.0211(7) 0.0415(10) 0.0164(7) -0.0042(7) 0.0042(6) 0.0011(7) C15 0.0215(8) 0.0292(8) 0.0299(9) -0.0034(7) 0.0076(6) 0.0002(6) C16 0.0225(8) 0.0368(9) 0.0227(8) 0.0073(7) 0.0085(6) 0.0048(7) F1 0.0375(6) 0.0590(7) 0.0193(5) -0.0085(5) 0.0039(4) -0.0008(5) F2 0.0390(6) 0.0316(6) 0.0467(7) -0.0058(5) 0.0083(5) -0.0034(5) F3 0.0389(6) 0.0454(6) 0.0313(6) 0.0156(5) 0.0132(5) 0.0081(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3387(18) . ? N1 C1 1.3432(18) . ? C1 C2 1.3935(19) . ? C1 C1 1.489(3) 3_655 ? C2 C3 1.3948(19) . ? C2 H2 0.9500 . ? C3 C4 1.399(2) . ? C3 C6 1.4364(19) . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.199(2) . ? C7 C8 1.4359(19) . ? C8 C9 1.401(2) . ? C8 C13 1.404(2) . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 C12 1.385(2) . ? C11 H11 0.9500 . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 F1 1.3390(17) . ? C14 C16 1.377(2) 3_767 ? C14 C15 1.379(2) . ? C15 F2 1.335(2) . ? C15 C16 1.381(2) . ? C16 F3 1.3376(18) . ? C16 C14 1.377(2) 3_767 ? 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 C5 N1 C1 117.05(12) . . ? N1 C1 C2 122.97(13) . . ? N1 C1 C1 116.47(15) . 3_655 ? C2 C1 C1 120.55(16) . 3_655 ? C1 C2 C3 119.23(13) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 118.12(13) . . ? C2 C3 C6 120.96(13) . . ? C4 C3 C6 120.92(13) . . ? C5 C4 C3 118.13(13) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 124.49(13) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? C7 C6 C3 179.17(16) . . ? C6 C7 C8 177.35(15) . . ? C9 C8 C13 119.43(13) . . ? C9 C8 C7 120.89(13) . . ? C13 C8 C7 119.67(13) . . ? C10 C9 C8 119.72(14) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.46(14) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.08(14) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 120.21(14) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 120.10(14) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? F1 C14 C16 119.96(15) . 3_767 ? F1 C14 C15 119.86(16) . . ? C16 C14 C15 120.18(14) 3_767 . ? F2 C15 C14 120.01(15) . . ? F2 C15 C16 120.14(15) . . ? C14 C15 C16 119.84(16) . . ? F3 C16 C14 120.22(14) . 3_767 ? F3 C16 C15 119.80(16) . . ? C14 C16 C15 119.98(15) 3_767 . ? 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 C5 N1 C1 C2 -0.5(2) . . . . ? C5 N1 C1 C1 179.05(15) . . . 3_655 ? N1 C1 C2 C3 -0.3(2) . . . . ? C1 C1 C2 C3 -179.92(15) 3_655 . . . ? C1 C2 C3 C4 1.0(2) . . . . ? C1 C2 C3 C6 -179.39(13) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C6 C3 C4 C5 179.64(13) . . . . ? C1 N1 C5 C4 0.8(2) . . . . ? C3 C4 C5 N1 -0.2(2) . . . . ? C2 C3 C6 C7 165(100) . . . . ? C4 C3 C6 C7 -16(12) . . . . ? C3 C6 C7 C8 49(13) . . . . ? C6 C7 C8 C9 136(3) . . . . ? C6 C7 C8 C13 -43(3) . . . . ? C13 C8 C9 C10 0.5(2) . . . . ? C7 C8 C9 C10 -178.00(14) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C9 C10 C11 C12 -0.4(2) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C8 0.3(2) . . . . ? C9 C8 C13 C12 -0.7(2) . . . . ? C7 C8 C13 C12 177.90(13) . . . . ? F1 C14 C15 F2 -0.6(2) . . . . ? C16 C14 C15 F2 178.89(14) 3_767 . . . ? F1 C14 C15 C16 -179.66(13) . . . . ? C16 C14 C15 C16 -0.1(3) 3_767 . . . ? F2 C15 C16 F3 0.5(2) . . . . ? C14 C15 C16 F3 179.51(13) . . . . ? F2 C15 C16 C14 -178.88(14) . . . 3_767 ? C14 C15 C16 C14 0.1(3) . . . 3_767 ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.304 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.049 _chemical_name_common "4,4'-diphenylethnyl-2,2'-bipyridine, hexafluorobenzene"