# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_1 _database_code_CSD 157246 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Batsanov, A. S.' 'Collings, J. C.' 'Howard, Judith A. K.' 'Marder, Todd B.' 'Roscoe, K. P.' 'Stimson, L. M.' 'Thomas, Rhodri Li' _publ_contact_author_name 'Prof Todd B Marder' _publ_contact_author_address ; Department of Chemistry University of Durnham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'TODD.MARDER@DURHAM.AC.UK' _publ_section_title ; Arene-perfluoroarene interactions in crystal engineering 3: single crystal structure of 1:1 complexes of octafluoronapthalene with fused ring polyaromatic compounds ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; perfluoronaphthalene anthracene complex (1:1) ; _chemical_name_common ? _chemical_melting_point '174--175\% C' _chemical_formula_moiety 'C10 F8,C14 H10' _chemical_formula_sum 'C24 H10 F8' _chemical_formula_weight 450.32 _ccdc_compound_id '1' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.810(1) _cell_length_b 18.326(1) _cell_length_c 7.390(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.35(1) _cell_angle_gamma 90.00 _cell_volume 907.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 435 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 25.3 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 1.00 0.00 0.2400 -1.00 -1.00 0.00 0.2400 0.00 1.00 0.00 0.0300 0.00 -1.00 0.00 0.0300 0.00 1.00 1.00 0.0300 0.00 -1.00 -1.00 0.0300 _exptl_special_details ; Four sets of \w scans (each scan 0.3\% in \w, exposure time 20 s), each set at different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. The first 50 scans (52 reflections) were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 6480 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2083 _reflns_number_gt 1205 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2083 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _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 F1 F -0.15250(17) -0.02211(5) 0.09406(13) 0.0306(3) Uani 1 1 d . . . F2 F -0.12562(16) 0.12346(6) 0.07511(14) 0.0330(3) Uani 1 1 d . . . F3 F -0.00395(17) 0.20440(5) 0.38149(15) 0.0320(3) Uani 1 1 d . . . F4 F 0.09646(16) 0.14022(5) 0.71343(15) 0.0308(3) Uani 1 1 d . . . C1 C -0.0844(3) 0.01591(10) 0.2494(2) 0.0216(4) Uani 1 1 d . . . C2 C -0.0729(3) 0.08959(10) 0.2384(2) 0.0230(4) Uani 1 1 d . . . C3 C -0.0109(3) 0.13137(9) 0.3963(3) 0.0238(4) Uani 1 1 d . . . C4 C 0.0397(3) 0.09819(9) 0.5624(2) 0.0214(4) Uani 1 1 d . . . C5 C 0.0325(3) 0.02136(9) 0.5810(2) 0.0188(4) Uani 1 1 d . . . C6 C 0.4389(3) 0.11322(10) 0.2316(3) 0.0254(5) Uani 1 1 d . . . H6 H 0.397(3) 0.1021(10) 0.102(3) 0.034(6) Uiso 1 1 d . . . C7 C 0.4673(3) 0.18411(11) 0.2843(3) 0.0304(5) Uani 1 1 d . . . H7 H 0.453(3) 0.2257(10) 0.194(3) 0.035(5) Uiso 1 1 d . . . C8 C 0.5258(3) 0.20259(11) 0.4734(3) 0.0298(5) Uani 1 1 d . . . H8 H 0.543(3) 0.2552(11) 0.508(3) 0.036(5) Uiso 1 1 d . . . C9 C 0.5548(3) 0.14956(10) 0.6035(3) 0.0261(5) Uani 1 1 d . . . H9 H 0.595(3) 0.1603(10) 0.727(3) 0.033(6) Uiso 1 1 d . . . C10 C 0.5279(3) 0.07402(9) 0.5553(3) 0.0224(4) Uani 1 1 d . . . C11 C 0.4683(3) 0.05523(10) 0.3640(3) 0.0216(4) Uani 1 1 d . . . C12 C 0.5584(3) 0.01814(10) 0.6859(3) 0.0232(4) Uani 1 1 d . . . H12 H 0.598(2) 0.0290(8) 0.814(2) 0.013(4) Uiso 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 F1 0.0382(7) 0.0313(6) 0.0209(6) -0.0016(5) 0.0011(5) -0.0062(5) F2 0.0386(8) 0.0324(6) 0.0275(7) 0.0113(5) 0.0043(5) 0.0022(5) F3 0.0398(7) 0.0170(6) 0.0409(7) 0.0055(5) 0.0119(5) 0.0016(5) F4 0.0408(8) 0.0227(6) 0.0290(6) -0.0059(5) 0.0066(5) -0.0030(5) C1 0.0194(10) 0.0256(11) 0.0197(10) -0.0036(9) 0.0036(8) -0.0025(8) C2 0.0210(11) 0.0267(11) 0.0219(11) 0.0091(9) 0.0051(8) 0.0037(8) C3 0.0224(10) 0.0196(10) 0.0312(12) 0.0044(9) 0.0094(9) 0.0012(8) C4 0.0186(11) 0.0206(10) 0.0255(12) -0.0057(9) 0.0057(8) -0.0014(8) C5 0.0148(10) 0.0197(9) 0.0224(10) -0.0007(8) 0.0049(8) 0.0006(7) C6 0.0207(11) 0.0285(11) 0.0259(12) 0.0031(10) 0.0012(9) -0.0003(9) C7 0.0255(12) 0.0254(12) 0.0397(14) 0.0082(10) 0.0045(10) 0.0029(8) C8 0.0267(12) 0.0193(10) 0.0433(14) -0.0014(10) 0.0057(10) 0.0004(9) C9 0.0220(12) 0.0232(11) 0.0322(13) -0.0064(9) 0.0023(9) -0.0006(8) C10 0.0146(10) 0.0219(10) 0.0313(12) 0.0011(9) 0.0054(9) 0.0018(8) C11 0.0157(10) 0.0217(10) 0.0272(11) -0.0013(9) 0.0031(8) -0.0008(7) C12 0.0210(11) 0.0262(10) 0.0219(11) -0.0014(9) 0.0027(8) -0.0003(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 F1 C1 1.3519(19) . ? F2 C2 1.3471(19) . ? F3 C3 1.3445(19) . ? F4 C4 1.3542(19) . ? C1 C2 1.356(2) . ? C1 C5 1.415(2) 3_556 ? C2 C3 1.396(2) . ? C3 C4 1.357(2) . ? C4 C5 1.417(2) . ? C5 C1 1.415(2) 3_556 ? C5 C5 1.432(3) 3_556 ? C6 C7 1.360(3) . ? C6 C11 1.434(2) . ? C7 C8 1.423(3) . ? C8 C9 1.357(3) . ? C9 C10 1.433(2) . ? C10 C12 1.397(3) . ? C10 C11 1.441(3) . ? C11 C12 1.397(2) 3_656 ? C12 C11 1.397(2) 3_656 ? 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 F1 C1 C2 118.49(16) . . ? F1 C1 C5 119.75(15) . 3_556 ? C2 C1 C5 121.74(17) . 3_556 ? F2 C2 C1 120.25(17) . . ? F2 C2 C3 119.20(16) . . ? C1 C2 C3 120.52(16) . . ? F3 C3 C4 120.85(17) . . ? F3 C3 C2 119.18(16) . . ? C4 C3 C2 119.97(16) . . ? F4 C4 C3 118.62(15) . . ? F4 C4 C5 119.66(16) . . ? C3 C4 C5 121.71(16) . . ? C1 C5 C4 123.95(16) 3_556 . ? C1 C5 C5 117.8(2) 3_556 3_556 ? C4 C5 C5 118.2(2) . 3_556 ? C7 C6 C11 121.12(19) . . ? C6 C7 C8 120.61(19) . . ? C9 C8 C7 120.34(19) . . ? C8 C9 C10 121.3(2) . . ? C12 C10 C9 122.68(17) . . ? C12 C10 C11 118.91(16) . . ? C9 C10 C11 118.41(16) . . ? C12 C11 C6 122.51(17) 3_656 . ? C12 C11 C10 119.29(17) 3_656 . ? C6 C11 C10 118.21(16) . . ? C10 C12 C11 121.81(18) . 3_656 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.050 #=========================================================================== #===========================END data_\a-2 _database_code_CSD 157247 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Batsanov, A. S.' 'Collings, J. C.' 'Howard, Judith A. K.' 'Marder, Todd B.' 'Roscoe, K. P.' 'Stimson, L. M.' 'Thomas, Rhodri Li' _publ_contact_author_name 'Prof Todd B Marder' _publ_contact_author_address ; Department of Chemistry University of Durnham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'TODD.MARDER@DURHAM.AC.UK' _publ_section_title ; Arene-perfluoroarene interactions in crystal engineering 3: single crystal structure of 1:1 complexes of octafluoronapthalene with fused ring polyaromatic compounds ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; perfluoronaphthalene phenanthrene complex (1:1) ; _chemical_name_common ? _chemical_melting_point '172--174\% C' _chemical_formula_moiety 'C10 F8,C14 H10' _chemical_formula_sum 'C24 H10 F8' _chemical_formula_weight 450.32 _ccdc_compound_id '\a-2' _ccdc_biological_activity '?' _ccdc_polymorph '\a (low-temperature) phase' _ccdc_disorder ; The phenanthrene molecule is disordered over two overlapping positions, related via an inversion centre; the atoms C(6) to C(19) and all H atoms have occupancies of 0.5. ; _ccdc_comments 'reversible phase transition to \b-2 ca. 250 K' 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' '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.776(2) _cell_length_b 18.180(6) _cell_length_c 7.666(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.45(1) _cell_angle_gamma 90.00 _cell_volume 922.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 294 _cell_measurement_theta_min 10 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9204 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details ? _exptl_special_details ; Three sets of \w scans (each scan 0.3\% in \w, exposure time 15 s), each set at different \f and/or 2\q angles, nominally covered a hemisphere of reciprocal space. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4586 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1621 _reflns_number_gt 942 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. Phenanthrene carbon atoms in isotropic approximation, other non-H atoms in anisotropic one. ; _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^)+(0.0624P)^2^+0.0711P] 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 1621 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1003 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 F1 F 0.3962(2) 0.60662(8) 0.1925(2) 0.0626(6) Uani 1 1 d . . . F2 F 0.4749(2) 0.70922(8) 0.4490(3) 0.0749(6) Uani 1 1 d . . . F3 F 0.5921(2) 0.67112(9) 0.7958(2) 0.0756(6) Uani 1 1 d . . . F4 F 0.6300(2) 0.53051(9) 0.8940(2) 0.0630(6) Uani 1 1 d . . . C1 C 0.4520(4) 0.58504(15) 0.3642(4) 0.0415(7) Uani 1 1 d . . . C2 C 0.4917(4) 0.63766(13) 0.4919(4) 0.0480(8) Uani 1 1 d . . . C3 C 0.5520(4) 0.61793(15) 0.6710(4) 0.0490(8) Uani 1 1 d . . . C4 C 0.5711(4) 0.54666(15) 0.7195(4) 0.0403(7) Uani 1 1 d . . . C5 C 0.5307(3) 0.48988(13) 0.5918(3) 0.0342(6) Uani 1 1 d . . . C6 C 0.4791(7) 0.8353(3) -0.0537(8) 0.0328(13) Uiso 0.50 1 d P . . H6 H 0.4453 0.8038 -0.1563 0.039 Uiso 0.50 1 d PR . . C7 C 0.5307(7) 0.8077(3) 0.1187(7) 0.0359(13) Uiso 0.50 1 d P . . H7 H 0.5321 0.7553 0.1334 0.043 Uiso 0.50 1 d PR . . C8 C 0.5808(7) 0.8529(3) 0.2672(7) 0.0372(13) Uiso 0.50 1 d P . . H8 H 0.6165 0.8317 0.3845 0.045 Uiso 0.50 1 d PR . . C9 C 0.5773(7) 0.9283(3) 0.2469(8) 0.0321(11) Uiso 0.50 1 d P . . H9 H 0.6108 0.9595 0.3502 0.039 Uiso 0.50 1 d PR . . C10 C 0.5648(7) 1.0905(3) 0.1926(7) 0.0282(11) Uiso 0.50 1 d P . . H10 H 0.6009 1.0719 0.3125 0.034 Uiso 0.50 1 d PR . . C11 C 0.5593(7) 1.1651(3) 0.1646(7) 0.0353(12) Uiso 0.50 1 d P . . H11 H 0.5895 1.1987 0.2634 0.042 Uiso 0.50 1 d PR . . C12 C 0.5065(7) 1.1921(3) -0.0140(8) 0.0326(12) Uiso 0.50 1 d P . . H12 H 0.5012 1.2442 -0.0351 0.039 Uiso 0.50 1 d PR . . C13 C 0.4642(7) 1.1457(3) -0.1526(7) 0.0335(12) Uiso 0.50 1 d P . . H13 H 0.4315 1.1647 -0.2722 0.040 Uiso 0.50 1 d PR . . C14 C 0.4210(7) 1.0191(3) -0.2729(6) 0.0327(11) Uiso 0.50 1 d P . . H14 H 0.3843 1.0391 -0.3914 0.039 Uiso 0.50 1 d PR . . C15 C 0.4269(7) 0.9458(3) -0.2488(7) 0.0335(12) Uiso 0.50 1 d P . . H15 H 0.3971 0.9138 -0.3506 0.040 Uiso 0.50 1 d PR . . C16 C 0.4771(7) 0.9139(3) -0.0742(7) 0.0281(11) Uiso 0.50 1 d P . . C17 C 0.5248(7) 0.9606(3) 0.0761(7) 0.0247(12) Uiso 0.50 1 d P . . C18 C 0.5197(6) 1.0408(3) 0.0505(6) 0.0261(11) Uiso 0.50 1 d P . . C19 C 0.4670(7) 1.0680(3) -0.1269(8) 0.0274(12) Uiso 0.50 1 d P . . 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 F1 0.0519(10) 0.0682(12) 0.0687(12) 0.0313(8) 0.0151(9) 0.0074(8) F2 0.0560(10) 0.0285(9) 0.1478(18) 0.0128(9) 0.0384(11) 0.0046(8) F3 0.0575(11) 0.0625(12) 0.1133(16) -0.0482(10) 0.0325(10) -0.0126(9) F4 0.0535(10) 0.0894(14) 0.0465(11) -0.0103(8) 0.0118(8) -0.0056(9) C1 0.0297(15) 0.0413(17) 0.0556(19) 0.0117(14) 0.0143(13) 0.0052(12) C2 0.0336(15) 0.0258(15) 0.090(2) 0.0066(15) 0.0247(15) 0.0048(11) C3 0.0331(16) 0.0430(18) 0.075(2) -0.0221(16) 0.0195(14) -0.0063(13) C4 0.0293(14) 0.0502(19) 0.0422(18) -0.0039(13) 0.0095(12) -0.0009(12) C5 0.0216(12) 0.0362(15) 0.0461(15) 0.0033(12) 0.0106(11) 0.0006(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.347(3) . ? F2 C2 1.341(3) . ? F3 C3 1.346(3) . ? F4 C4 1.343(3) . ? C1 C2 1.354(4) . ? C1 C5 1.402(3) 3_666 ? C2 C3 1.392(4) . ? C3 C4 1.347(4) . ? C4 C5 1.409(3) . ? C5 C1 1.402(3) 3_666 ? C5 C5 1.427(5) 3_666 ? C6 C7 1.386(8) . ? C6 C16 1.437(7) . ? C7 C8 1.385(7) . ? C8 C9 1.380(7) . ? C9 C17 1.409(7) . ? C10 C11 1.371(7) . ? C10 C18 1.397(7) . ? C11 C12 1.426(8) . ? C12 C13 1.339(8) . ? C13 C19 1.426(8) . ? C14 C15 1.344(7) . ? C14 C19 1.411(6) . ? C15 C16 1.431(7) . ? C16 C17 1.411(7) . ? C17 C18 1.472(7) . ? C18 C19 1.418(8) . ? 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 F1 C1 C2 118.1(2) . . ? F1 C1 C5 120.6(2) . 3_666 ? C2 C1 C5 121.2(2) . 3_666 ? F2 C2 C1 121.0(3) . . ? F2 C2 C3 118.9(3) . . ? C1 C2 C3 120.1(2) . . ? F3 C3 C4 120.1(3) . . ? F3 C3 C2 119.2(3) . . ? C4 C3 C2 120.7(2) . . ? F4 C4 C3 118.4(2) . . ? F4 C4 C5 120.2(2) . . ? C3 C4 C5 121.3(2) . . ? C1 C5 C4 123.4(2) 3_666 . ? C1 C5 C5 118.7(3) 3_666 3_666 ? C4 C5 C5 117.9(3) . 3_666 ? C7 C6 C16 117.3(5) . . ? C8 C7 C6 122.4(6) . . ? C9 C8 C7 120.1(5) . . ? C8 C9 C17 120.9(5) . . ? C11 C10 C18 121.5(5) . . ? C10 C11 C12 118.9(5) . . ? C13 C12 C11 120.8(6) . . ? C12 C13 C19 121.4(5) . . ? C15 C14 C19 121.4(5) . . ? C14 C15 C16 121.6(5) . . ? C17 C16 C15 119.1(5) . . ? C17 C16 C6 120.9(5) . . ? C15 C16 C6 120.0(5) . . ? C9 C17 C16 118.4(5) . . ? C9 C17 C18 122.0(5) . . ? C16 C17 C18 119.5(6) . . ? C10 C18 C19 119.4(5) . . ? C10 C18 C17 122.8(5) . . ? C19 C18 C17 117.8(6) . . ? C14 C19 C18 120.6(5) . . ? C14 C19 C13 121.4(6) . . ? C18 C19 C13 118.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.064 #=========================================================================== #=============END data_\b-2 _database_code_CSD 157248 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Batsanov, A. S.' 'Collings, J. C.' 'Howard, Judith A. K.' 'Marder, Todd B.' 'Roscoe, K. P.' 'Stimson, L. M.' 'Thomas, Rhodri Li' _publ_contact_author_name 'Prof Todd B Marder' _publ_contact_author_address ; Department of Chemistry University of Durnham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'TODD.MARDER@DURHAM.AC.UK' _publ_section_title ; Arene-perfluoroarene interactions in crystal engineering 3: single crystal structure of 1:1 complexes of octafluoronapthalene with fused ring polyaromatic compounds ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; perfluoronaphthalene phenanthrene complex (1:1) ; _chemical_name_common ? _chemical_melting_point '172--174\% C' _chemical_formula_moiety 'C10 F8,C14 H10' _chemical_formula_sum 'C24 H10 F8' _chemical_formula_weight 450.32 _ccdc_compound_id '\a-2' _ccdc_biological_activity '?' _ccdc_polymorph '\b (high-temperature) phase' _ccdc_disorder ; Both molecules disordered, no satisfactory model found. ; _ccdc_comments 'reversible phase transition to \a-2 ca. 250 K' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/m #loop_ #_symmetry_equiv_pos_as_xyz #'x, y, z' #'-x+1/2, y+1/2, -z+1/2' #'-x, -y, -z' #'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.923(2) _cell_length_b 17.925(3) _cell_length_c 8.080(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.39(1) _cell_angle_gamma 90.00 _cell_volume 971.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 119 _cell_measurement_theta_min 10 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.14 _exptl_absorpt_correction_type none _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (20 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 18 duplicate reflections. ; _diffrn_ambient_temperature 295(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.3 _diffrn_reflns_number 3499 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.5 _reflns_number_total 1145 _reflns_number_gt 319 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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' 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 ? ? ? ? ? ? ? ? ? ? ? ? ? #=========================================================================== #=============END data_3 _database_code_CSD 157249 _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Batsanov, A. S.' 'Collings, J. C.' 'Howard, Judith A. K.' 'Marder, Todd B.' 'Roscoe, K. P.' 'Stimson, L. M.' 'Thomas, Rhodri Li' _publ_contact_author_name 'Prof Todd B Marder' _publ_contact_author_address ; Department of Chemistry University of Durnham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email 'TODD.MARDER@DURHAM.AC.UK' _publ_section_title ; Arene-perfluoroarene interactions in crystal engineering 3: single crystal structure of 1:1 complexes of octafluoronapthalene with fused ring polyaromatic compounds ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; perfluoronaphthalene pyrene complex (1:1) ; _chemical_name_common ? _chemical_melting_point '248--250\% C' _chemical_formula_moiety 'C10 F8,C16 H10' _chemical_formula_sum 'C26 H10 F8' _chemical_formula_weight 474.34 _ccdc_compound_id '3' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_disorder 'none' _ccdc_comments '?' 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' '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 6.725(1) _cell_length_b 8.864(1) _cell_length_c 9.488(1) _cell_angle_alpha 107.51(1) _cell_angle_beta 105.23(1) _cell_angle_gamma 106.82(1) _cell_volume 476.9(1) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 331 _cell_measurement_theta_min 10.3 _cell_measurement_theta_max 26.3 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Four sets of \w scans (each scan 0.3\% in \w, exposure time 20 s), each set at different \f and/or 2\q angles, nominally covered over a hemisphere of reciprocal space. The first 50 scans (36 reflections) were repeated at the end of data collection, revealing no significant crystal decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 2866 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1661 _reflns_number_gt 1106 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. ; _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^)+(0.0591P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1661 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 F1 F 0.3891(2) 0.14979(16) 0.51281(15) 0.0321(4) Uani 1 1 d . . . F2 F 0.2314(2) 0.02898(16) 0.19297(16) 0.0395(4) Uani 1 1 d . . . F3 F 0.2519(2) 0.24496(17) 0.04342(14) 0.0362(4) Uani 1 1 d . . . F4 F 0.4302(2) 0.58963(17) 0.21227(15) 0.0316(4) Uani 1 1 d . . . C1 C 0.4016(3) 0.2628(3) 0.4434(3) 0.0231(5) Uani 1 1 d . . . C2 C 0.3216(4) 0.2002(3) 0.2822(3) 0.0270(6) Uani 1 1 d . . . C3 C 0.3320(4) 0.3123(3) 0.2038(3) 0.0257(5) Uani 1 1 d . . . C4 C 0.4211(3) 0.4856(3) 0.2916(3) 0.0222(5) Uani 1 1 d . . . C5 C 0.5057(3) 0.5579(3) 0.4602(3) 0.0198(5) Uani 1 1 d . . . C6 C 0.7820(4) 0.3044(3) 0.0795(3) 0.0286(6) Uani 1 1 d . . . H6 H 0.721(4) 0.249(3) -0.031(3) 0.032(7) Uiso 1 1 d . . . C7 C 0.7809(4) 0.2024(3) 0.1654(3) 0.0267(6) Uani 1 1 d . . . H7 H 0.719(4) 0.081(3) 0.113(3) 0.033(7) Uiso 1 1 d . . . C8 C 0.8657(3) 0.2765(3) 0.3327(3) 0.0219(5) Uani 1 1 d . . . C9 C 0.9554(3) 0.4598(3) 0.4147(3) 0.0200(5) Uani 1 1 d . . . C10 C 0.9572(3) 0.5639(3) 0.3245(3) 0.0219(5) Uani 1 1 d . . . C11 C 0.8684(4) 0.4828(3) 0.1574(3) 0.0262(6) Uani 1 1 d . . . H11 H 0.869(4) 0.552(3) 0.095(3) 0.027(6) Uiso 1 1 d . . . C12 C 0.8677(4) 0.1760(3) 0.4274(3) 0.0257(5) Uani 1 1 d . . . H12 H 0.807(4) 0.055(3) 0.373(3) 0.034(7) Uiso 1 1 d . . . C13 C 0.9503(4) 0.2510(3) 0.5885(3) 0.0254(6) Uani 1 1 d . . . H13 H 0.950(4) 0.188(3) 0.649(3) 0.040(7) Uiso 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 F1 0.0375(8) 0.0259(7) 0.0435(9) 0.0229(6) 0.0198(7) 0.0141(6) F2 0.0425(9) 0.0238(8) 0.0399(9) 0.0036(6) 0.0144(7) 0.0078(7) F3 0.0339(8) 0.0463(9) 0.0215(8) 0.0083(6) 0.0072(6) 0.0155(7) F4 0.0340(8) 0.0413(8) 0.0322(8) 0.0257(6) 0.0154(6) 0.0188(7) C1 0.0158(12) 0.0271(13) 0.0330(14) 0.0176(11) 0.0123(10) 0.0093(10) C2 0.0217(13) 0.0226(12) 0.0334(14) 0.0071(11) 0.0121(11) 0.0076(10) C3 0.0185(12) 0.0358(14) 0.0203(13) 0.0079(11) 0.0079(10) 0.0106(11) C4 0.0180(12) 0.0326(13) 0.0255(13) 0.0196(11) 0.0102(10) 0.0130(11) C5 0.0132(11) 0.0263(13) 0.0260(13) 0.0140(10) 0.0094(10) 0.0110(10) C6 0.0268(13) 0.0375(14) 0.0232(14) 0.0113(12) 0.0103(11) 0.0159(11) C7 0.0215(13) 0.0302(14) 0.0282(14) 0.0097(11) 0.0103(10) 0.0114(11) C8 0.0153(12) 0.0256(13) 0.0288(13) 0.0130(10) 0.0106(10) 0.0098(10) C9 0.0129(11) 0.0265(12) 0.0251(12) 0.0132(10) 0.0099(9) 0.0088(9) C10 0.0157(11) 0.0309(13) 0.0270(13) 0.0163(10) 0.0111(10) 0.0126(10) C11 0.0253(13) 0.0401(14) 0.0277(14) 0.0221(12) 0.0158(11) 0.0187(11) C12 0.0236(13) 0.0231(13) 0.0341(15) 0.0131(11) 0.0145(11) 0.0099(11) C13 0.0238(13) 0.0311(14) 0.0346(15) 0.0227(12) 0.0155(11) 0.0153(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.350(2) . ? F2 C2 1.346(3) . ? F3 C3 1.342(2) . ? F4 C4 1.353(2) . ? C1 C2 1.350(3) . ? C1 C5 1.415(3) 2_666 ? C2 C3 1.405(3) . ? C3 C4 1.359(3) . ? C4 C5 1.410(3) . ? C5 C1 1.415(3) 2_666 ? C5 C5 1.442(4) 2_666 ? C6 C11 1.387(3) . ? C6 C7 1.387(3) . ? C6 H6 0.93(2) . ? C7 C8 1.399(3) . ? C7 H7 0.94(2) . ? C8 C9 1.427(3) . ? C8 C12 1.443(3) . ? C9 C9 1.426(4) 2_766 ? C9 C10 1.435(3) . ? C10 C11 1.398(3) . ? C10 C13 1.445(3) 2_766 ? C11 H11 0.97(2) . ? C12 C13 1.347(3) . ? C12 H12 0.94(2) . ? C13 C10 1.445(3) 2_766 ? C13 H13 0.92(2) . ? 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 F1 C1 C2 118.5(2) . . ? F1 C1 C5 119.80(19) . 2_666 ? C2 C1 C5 121.7(2) . 2_666 ? F2 C2 C1 120.6(2) . . ? F2 C2 C3 118.6(2) . . ? C1 C2 C3 120.8(2) . . ? F3 C3 C4 121.5(2) . . ? F3 C3 C2 118.9(2) . . ? C4 C3 C2 119.5(2) . . ? F4 C4 C3 117.92(19) . . ? F4 C4 C5 119.98(19) . . ? C3 C4 C5 122.1(2) . . ? C4 C5 C1 124.14(19) . 2_666 ? C4 C5 C5 118.1(2) . 2_666 ? C1 C5 C5 117.8(2) 2_666 2_666 ? C11 C6 C7 120.8(2) . . ? C11 C6 H6 121.5(14) . . ? C7 C6 H6 117.7(14) . . ? C6 C7 C8 121.0(2) . . ? C6 C7 H7 121.0(14) . . ? C8 C7 H7 118.0(14) . . ? C7 C8 C9 118.9(2) . . ? C7 C8 C12 123.1(2) . . ? C9 C8 C12 118.0(2) . . ? C9 C9 C8 120.6(2) 2_766 . ? C9 C9 C10 119.8(3) 2_766 . ? C8 C9 C10 119.5(2) . . ? C11 C10 C9 119.1(2) . . ? C11 C10 C13 122.9(2) . 2_766 ? C9 C10 C13 118.0(2) . 2_766 ? C6 C11 C10 120.7(2) . . ? C6 C11 H11 119.5(13) . . ? C10 C11 H11 119.8(14) . . ? C13 C12 C8 121.8(2) . . ? C13 C12 H12 120.7(14) . . ? C8 C12 H12 117.6(14) . . ? C12 C13 C10 121.7(2) . 2_766 ? C12 C13 H13 122.2(16) . . ? C10 C13 H13 116.0(16) 2_766 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.200 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.050 #=========================================================================== #===================END