# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _publ_contact_author 'Andrei S.Batsanov' _publ_contact_author_email a.s.batsanov@durham.ac.uk loop_ _publ_author_name 'Collings, Jonathan C.' 'Roscoe, Karl P.' 'Batsanov, Andrei S.' 'Stimson, Lorna M.' 'Clark, Stewart J.' 'Howard, Judith A. K.' 'Marder, Todd B.' _journal_name_full 'New Journal of Chemistry' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '2002' _publ_section_title ;Arene =96 perfluoroarene interactions in crystal engineering 8. Structures of 1:1 complexes of hexafluorobenzene with fused-ring polyaromatic hydrocarbons ; #=========================================================================== #================================================================= data_(1) _database_code_CSD 175695 _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexafluorobenzene : naphthalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8,C6 F6' _chemical_formula_sum 'C16 H8 F6' _chemical_formula_weight 314.22 _ccdc_compound_id '1' _ccdc_polymorph 'high-T phase, transition at 175 K' _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 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.806(1) _cell_length_b 13.508(1) _cell_length_c 8.426(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.15(1) _cell_angle_gamma 90.00 _cell_volume 1333.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 574 _cell_measurement_theta_min 12 _cell_measurement_theta_max 26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type none _exptl_absorpt_correction_t_max ? _exptl_absorpt_correction_t_min ? _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 were repeated at the end of data collection, intensities of 58 duplicate reflections revealing no significant decay. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 180(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_decay_% 0 _diffrn_reflns_number 4725 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1530 _reflns_number_gt 1083 _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^)+(0.0374P)^2^+1.0889P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1530 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5000 0.11823(19) 0.7500 0.0437(6) Uani 1 2 d S . . C2 C 0.55857(16) 0.16880(15) 0.6450(2) 0.0428(4) Uani 1 1 d . . . C3 C 0.55947(15) 0.27102(14) 0.6454(2) 0.0398(4) Uani 1 1 d . . . C4 C 0.5000 0.32207(18) 0.7500 0.0381(6) Uani 1 2 d S . . F1 F 0.5000 0.01867(12) 0.7500 0.0654(5) Uani 1 2 d S . . F2 F 0.61451(12) 0.11958(10) 0.54028(16) 0.0651(4) Uani 1 1 d . . . F3 F 0.61805(11) 0.32049(10) 0.54476(15) 0.0604(4) Uani 1 1 d . . . F4 F 0.5000 0.42154(11) 0.7500 0.0553(5) Uani 1 2 d S . . C11 C 0.27045(17) 0.11705(15) 0.4488(3) 0.0447(5) Uani 1 1 d . . . H11 H 0.306(2) 0.0833(17) 0.376(3) 0.057(7) Uiso 1 1 d . . . C12 C 0.21116(19) 0.07087(16) 0.5572(3) 0.0531(6) Uani 1 1 d . . . H12 H 0.206(2) -0.0017(19) 0.561(3) 0.060(6) Uiso 1 1 d . . . C13 C 0.15703(19) 0.12595(17) 0.6659(3) 0.0520(5) Uani 1 1 d . . . H13 H 0.116(2) 0.0938(18) 0.740(3) 0.069(7) Uiso 1 1 d . . . C14 C 0.16150(16) 0.22692(16) 0.6657(2) 0.0447(5) Uani 1 1 d . . . H14 H 0.124(2) 0.2663(16) 0.743(3) 0.056(6) Uiso 1 1 d . . . C15 C 0.22224(14) 0.27807(13) 0.55507(19) 0.0345(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 C1 0.0466(15) 0.0312(13) 0.0500(15) 0.000 -0.0065(12) 0.000 C2 0.0408(10) 0.0443(11) 0.0419(10) -0.0085(9) -0.0006(8) 0.0039(8) C3 0.0345(9) 0.0467(11) 0.0372(9) 0.0028(8) 0.0006(7) -0.0079(8) C4 0.0341(13) 0.0332(13) 0.0441(14) 0.000 -0.0064(11) 0.000 F1 0.0772(13) 0.0326(9) 0.0832(13) 0.000 -0.0030(10) 0.000 F2 0.0674(9) 0.0672(9) 0.0625(8) -0.0231(6) 0.0149(6) 0.0080(6) F3 0.0599(8) 0.0666(8) 0.0567(7) 0.0072(6) 0.0156(6) -0.0151(6) F4 0.0574(10) 0.0321(8) 0.0729(11) 0.000 -0.0059(8) 0.000 C11 0.0440(11) 0.0397(11) 0.0480(11) -0.0063(9) -0.0038(9) 0.0031(8) C12 0.0561(13) 0.0358(11) 0.0621(13) 0.0077(10) -0.0131(10) -0.0100(9) C13 0.0456(12) 0.0589(13) 0.0504(12) 0.0159(10) 0.0023(9) -0.0147(10) C14 0.0375(10) 0.0576(13) 0.0389(10) 0.0023(9) 0.0049(8) -0.0007(9) C15 0.0295(9) 0.0379(9) 0.0344(9) 0.0005(7) -0.0024(7) -0.0012(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 C1 F1 1.345(3) . ? C1 C2 1.371(2) 2_656 ? C1 C2 1.371(2) . ? C2 F2 1.342(2) . ? C2 C3 1.381(3) . ? C3 F3 1.338(2) . ? C3 C4 1.378(2) . ? C4 F4 1.344(3) . ? C4 C3 1.378(2) 2_656 ? C11 C12 1.369(3) . ? C11 C15 1.420(3) 7_556 ? C11 H11 0.90(2) . ? C12 C13 1.395(3) . ? C12 H12 0.98(3) . ? C13 C14 1.365(3) . ? C13 H13 0.94(3) . ? C14 C15 1.423(3) . ? C14 H14 0.99(2) . ? C15 C11 1.420(3) 7_556 ? C15 C15 1.420(3) 7_556 ? 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 119.88(12) . 2_656 ? F1 C1 C2 119.88(12) . . ? C2 C1 C2 120.2(2) 2_656 . ? F2 C2 C1 120.42(18) . . ? F2 C2 C3 119.52(18) . . ? C1 C2 C3 120.06(18) . . ? F3 C3 C4 120.01(18) . . ? F3 C3 C2 120.15(17) . . ? C4 C3 C2 119.84(18) . . ? F4 C4 C3 120.02(12) . 2_656 ? F4 C4 C3 120.02(12) . . ? C3 C4 C3 120.0(2) 2_656 . ? C12 C11 C15 120.5(2) . 7_556 ? C12 C11 H11 122.5(15) . . ? C15 C11 H11 117.0(15) 7_556 . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 120.8(14) . . ? C13 C12 H12 118.6(14) . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.1(16) . . ? C12 C13 H13 120.1(15) . . ? C13 C14 C15 120.57(19) . . ? C13 C14 H14 121.0(13) . . ? C15 C14 H14 118.4(13) . . ? C11 C15 C15 118.9(2) 7_556 7_556 ? C11 C15 C14 122.42(18) 7_556 . ? C15 C15 C14 118.7(2) 7_556 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.179 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.037 #=========================================================================== #=========END data_(2) _database_code_CSD 175696 _audit_creation_method SHELXL _chemical_name_systematic ; hexafluorobenzene : anthracene ; _chemical_name_common ? _chemical_formula_moiety 'C14 H10,C6 F6' _chemical_formula_sum 'C20 H10 F6' _chemical_formula_weight 364.28 _chemical_melting_point ? _chemical_compound_source ? _ccdc_compound_id 'ZZZGMW01' _ccdc_comments 'ZZZGMW has a==9.03,b==12.2,c==7.26 \%A,\b==95\%, space group C2(/m)' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.122(3) _cell_length_b 12.086(2) _cell_length_c 8.955(2) _cell_angle_alpha 90.00 _cell_angle_beta 118.39(3) _cell_angle_gamma 90.00 _cell_volume 1535.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.0 _cell_measurement_theta_max 32.5 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'Not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 1.249 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8892 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'TEXSAN V5.1 (MSC,1989) on 108 \y-scans of 3 reflections' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC6S 4-circle diffractometer' _diffrn_measurement_method '2\q/\w' _diffrn_standards_number 3 _diffrn_standards_interval_count 147 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.12 _diffrn_reflns_number 1608 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.81 _diffrn_reflns_theta_max 75.03 _reflns_number_total 1279 _reflns_number_observed 1133 _reflns_observed_criterion I>2\s(I) _computing_data_collection MSC/AFC _computing_cell_refinement MSC/AFC _computing_data_reduction TEXSAN _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 11 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.0962P)^2^+1.0534P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1268 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_obs 0.0501 _refine_ls_wR_factor_all 0.1551 _refine_ls_wR_factor_obs 0.1437 _refine_ls_goodness_of_fit_all 1.049 _refine_ls_goodness_of_fit_obs 1.076 _refine_ls_restrained_S_all 1.091 _refine_ls_restrained_S_obs 1.076 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.24817(11) 0.36525(14) 0.5117(2) 0.0243(4) Uani 1 d . . H1 H 0.2476(12) 0.4440(18) 0.5235(21) 0.026(5) Uiso 1 d . . C2 C 0.28572(11) 0.31787(14) 0.4142(2) 0.0232(4) Uani 1 d . . C3 C 0.32340(13) 0.3826(2) 0.3267(2) 0.0293(4) Uani 1 d . . H3 H 0.3206(15) 0.4617(20) 0.3414(26) 0.041(6) Uiso 1 d . . C4 C 0.35844(14) 0.3335(2) 0.2322(2) 0.0334(5) Uani 1 d . . H4 H 0.3834(16) 0.3780(22) 0.1828(30) 0.051(7) Uiso 1 d . . C5 C 0.36003(15) 0.2165(2) 0.2196(2) 0.0333(5) Uani 1 d . . H5 H 0.3857(15) 0.1878(21) 0.1544(28) 0.042(6) Uiso 1 d . . C6 C 0.32629(13) 0.1517(2) 0.3024(2) 0.0289(5) Uani 1 d . . H6 H 0.3274(15) 0.0690(21) 0.2930(27) 0.044(6) Uiso 1 d . . C7 C 0.28727(11) 0.19875(14) 0.4021(2) 0.0230(4) Uani 1 d . . C11 C 0.5000 0.1177(2) 0.7500 0.0277(6) Uani 1 d S . C12 C 0.53673(11) 0.1736(2) 0.6617(2) 0.0275(5) Uani 1 d . . C13 C 0.53692(12) 0.2881(2) 0.6613(2) 0.0295(5) Uani 1 d . . C14 C 0.5000 0.3437(2) 0.7500 0.0308(6) Uani 1 d S . F11 F 0.5000 0.00631(13) 0.7500 0.0427(5) Uani 1 d S . F12 F 0.57298(8) 0.11795(11) 0.57671(12) 0.0384(4) Uani 1 d . . F13 F 0.57270(8) 0.34264(11) 0.57532(13) 0.0409(4) Uani 1 d . . F14 F 0.5000 0.45495(14) 0.7500 0.0479(5) Uani 1 d S . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0281(10) 0.0205(7) 0.0262(8) -0.0013(6) 0.0145(7) 0.0008(7) C2 0.0226(9) 0.0266(9) 0.0212(7) 0.0003(6) 0.0110(7) 0.0001(7) C3 0.0327(10) 0.0293(9) 0.0305(8) 0.0046(7) 0.0187(7) -0.0007(8) C4 0.0361(10) 0.0415(11) 0.0313(9) 0.0048(7) 0.0230(8) -0.0017(9) C5 0.0349(11) 0.0438(12) 0.0301(9) -0.0032(7) 0.0227(8) 0.0024(9) C6 0.0307(10) 0.0318(10) 0.0288(8) -0.0040(6) 0.0180(7) 0.0009(8) C7 0.0225(9) 0.0265(9) 0.0216(7) -0.0015(6) 0.0118(6) 0.0020(7) C11 0.0331(14) 0.0272(12) 0.0247(10) 0.000 0.0153(10) 0.000 C12 0.0264(9) 0.0390(11) 0.0216(8) -0.0014(6) 0.0151(7) 0.0037(8) C13 0.0269(10) 0.0384(11) 0.0251(8) 0.0044(6) 0.0139(7) -0.0027(8) C14 0.0299(14) 0.0263(13) 0.0338(12) 0.000 0.0131(10) 0.000 F11 0.0655(12) 0.0282(9) 0.0442(8) 0.000 0.0339(8) 0.000 F12 0.0447(7) 0.0500(7) 0.0321(6) -0.0046(5) 0.0277(5) 0.0064(5) F13 0.0401(7) 0.0513(8) 0.0389(6) 0.0107(5) 0.0248(5) -0.0086(5) F14 0.0557(11) 0.0267(9) 0.0621(10) 0.000 0.0286(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7 1.393(2) 7_556 ? C1 C2 1.400(2) . ? C2 C3 1.431(2) . ? C2 C7 1.445(2) . ? C3 C4 1.358(3) . ? C4 C5 1.420(3) . ? C5 C6 1.357(3) . ? C6 C7 1.431(2) . ? C7 C1 1.393(2) 7_556 ? C11 F11 1.346(3) . ? C11 C12 1.371(2) 2_656 ? C11 C12 1.371(2) . ? C12 F12 1.340(2) . ? C12 C13 1.384(3) . ? C13 F13 1.335(2) . ? C13 C14 1.373(2) . ? C14 F14 1.344(3) . ? C14 C13 1.373(2) 2_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 C7 C1 C2 122.1(2) 7_556 . ? C1 C2 C3 122.7(2) . . ? C1 C2 C7 118.84(15) . . ? C3 C2 C7 118.50(15) . . ? C4 C3 C2 120.8(2) . . ? C3 C4 C5 120.9(2) . . ? C6 C5 C4 120.3(2) . . ? C5 C6 C7 121.4(2) . . ? C1 C7 C6 122.9(2) 7_556 . ? C1 C7 C2 119.04(15) 7_556 . ? C6 C7 C2 118.08(15) . . ? F11 C11 C12 119.57(12) . 2_656 ? F11 C11 C12 119.56(12) . . ? C12 C11 C12 120.9(2) 2_656 . ? F12 C12 C11 120.3(2) . . ? F12 C12 C13 119.9(2) . . ? C11 C12 C13 119.8(2) . . ? F13 C13 C14 121.1(2) . . ? F13 C13 C12 119.8(2) . . ? C14 C13 C12 119.1(2) . . ? F14 C14 C13 119.30(12) . 2_656 ? F14 C14 C13 119.30(12) . . ? C13 C14 C13 121.4(2) 2_656 . ? _refine_diff_density_max 0.301 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.062 #=========================================================================== #=========END data_(3) _database_code_CSD 175697 _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexafluorobenzene : phenanthrene complex (1:1) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 F6,C14 H10' _chemical_formula_sum 'C20 H10 F6' _chemical_formula_weight 364.28 _ccdc_compound_id '3' _ccdc_disorder ; The phenanthrene molecule is disordered over two positions, with occupancies 87.3(2)% (unprimed labels) and 12.7(2)% (primed labels), which were refined independently. ; 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 6.929(2) _cell_length_b 7.308(1) _cell_length_c 15.991(3) _cell_angle_alpha 91.51(1) _cell_angle_beta 102.16(1) _cell_angle_gamma 100.16(1) _cell_volume 777.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 760 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 26.4 _exptl_crystal_description splinter _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (10 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 110 duplicate reflections. Crystal-to-detector distance 4.5 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_decay_% 0 _diffrn_reflns_number 9769 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 29.13 _reflns_number_total 4080 _reflns_number_gt 3056 _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^)+(0.0676P)^2^+0.1557P] 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 4080 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.17722(19) 0.54956(18) 0.78140(9) 0.0323(3) Uani 1 1 d . . . C2 C 0.18582(19) 0.56089(17) 0.69606(8) 0.0308(3) Uani 1 1 d . . . C3 C 0.23835(18) 0.73275(18) 0.66465(8) 0.0295(3) Uani 1 1 d . . . C4 C 0.28050(18) 0.89289(17) 0.71858(8) 0.0302(3) Uani 1 1 d . . . C5 C 0.27093(18) 0.88089(18) 0.80376(9) 0.0310(3) Uani 1 1 d . . . C6 C 0.21939(19) 0.70912(19) 0.83535(8) 0.0314(3) Uani 1 1 d . . . F1 F 0.12864(13) 0.38249(12) 0.81211(6) 0.0459(2) Uani 1 1 d . . . F2 F 0.14272(13) 0.40623(11) 0.64376(6) 0.0446(2) Uani 1 1 d . . . F3 F 0.24944(12) 0.74441(13) 0.58224(5) 0.0410(2) Uani 1 1 d . . . F4 F 0.33194(13) 1.05951(11) 0.68811(6) 0.0425(2) Uani 1 1 d . . . F5 F 0.31169(13) 1.03708(12) 0.85556(6) 0.0450(2) Uani 1 1 d . . . F6 F 0.20914(13) 0.69771(13) 0.91778(5) 0.0443(2) Uani 1 1 d . . . C7 C 0.7236(2) 0.6645(3) 0.55867(10) 0.0295(3) Uani 0.873(2) 1 d P A 1 H7 H 0.6985 0.5583 0.5197 0.035 Uiso 0.873(2) 1 d PR A 1 C8 C 0.7711(2) 0.8385(3) 0.53009(9) 0.0325(3) Uani 0.873(2) 1 d P A 1 H8 H 0.7779 0.8522 0.4718 0.039 Uiso 0.873(2) 1 d PR A 1 C9 C 0.8099(2) 0.9973(3) 0.58742(10) 0.0327(3) Uani 0.873(2) 1 d P A 1 H9 H 0.8417 1.1180 0.5676 0.039 Uiso 0.873(2) 1 d PR A 1 C10 C 0.8021(2) 0.9792(2) 0.67194(9) 0.0267(3) Uani 0.873(2) 1 d P A 1 H10 H 0.8307 1.0874 0.7099 0.032 Uiso 0.873(2) 1 d PR A 1 C11 C 0.7805(2) 0.9283(2) 0.85508(9) 0.0283(3) Uani 0.873(2) 1 d P A 1 H11 H 0.8160 1.0516 0.8386 0.034 Uiso 0.873(2) 1 d PR A 1 C12 C 0.7668(2) 0.8988(3) 0.93892(10) 0.0358(4) Uani 0.873(2) 1 d P A 1 H12 H 0.7905 1.0029 0.9790 0.043 Uiso 0.873(2) 1 d PR A 1 C13 C 0.7181(3) 0.7172(4) 0.96478(10) 0.0391(4) Uani 0.873(2) 1 d P A 1 H13 H 0.7107 0.6987 1.0227 0.047 Uiso 0.873(2) 1 d PR A 1 C14 C 0.6816(2) 0.5675(3) 0.90637(10) 0.0344(3) Uani 0.873(2) 1 d P A 1 H14 H 0.6498 0.4453 0.9246 0.041 Uiso 0.873(2) 1 d PR A 1 C15 C 0.6487(2) 0.43707(19) 0.75822(10) 0.0304(3) Uani 0.873(2) 1 d P A 1 H15 H 0.6133 0.3153 0.7764 0.036 Uiso 0.873(2) 1 d PR A 1 C16 C 0.6578(2) 0.45964(19) 0.67532(10) 0.0289(3) Uani 0.873(2) 1 d P A 1 H16 H 0.6286 0.3533 0.6362 0.035 Uiso 0.873(2) 1 d PR A 1 C17 C 0.71115(19) 0.6419(2) 0.64554(9) 0.0240(3) Uani 0.873(2) 1 d P A 1 C18 C 0.75216(18) 0.8015(2) 0.70359(9) 0.0215(3) Uani 0.873(2) 1 d P A 1 C19 C 0.74216(18) 0.7768(2) 0.79310(8) 0.0221(3) Uani 0.873(2) 1 d P A 1 C20 C 0.6914(2) 0.5941(2) 0.81951(9) 0.0262(3) Uani 0.873(2) 1 d P A 1 C7' C 0.7961(18) 0.913(2) 0.5893(8) 0.033(3) Uiso 0.127(2) 1 d P A 2 H7' H 0.8287 1.0356 0.5712 0.040 Uiso 0.127(2) 1 d PR A 2 C8' C 0.7591(18) 0.755(2) 0.5359(8) 0.025(2) Uiso 0.127(2) 1 d P A 2 H8' H 0.7640 0.7662 0.4773 0.030 Uiso 0.127(2) 1 d PR A 2 C9' C 0.7158(19) 0.582(2) 0.5574(8) 0.035(3) Uiso 0.127(2) 1 d P A 2 H9' H 0.6959 0.4791 0.5172 0.042 Uiso 0.127(2) 1 d PR A 2 C10' C 0.6995(16) 0.550(2) 0.6415(7) 0.028(2) Uiso 0.127(2) 1 d P A 2 H10' H 0.6658 0.4252 0.6568 0.033 Uiso 0.127(2) 1 d PR A 2 C11' C 0.6732(16) 0.4879(19) 0.8209(7) 0.033(2) Uiso 0.127(2) 1 d P A 2 H11' H 0.6434 0.3820 0.7815 0.040 Uiso 0.127(2) 1 d PR A 2 C12' C 0.6655(19) 0.462(2) 0.9050(8) 0.041(3) Uiso 0.127(2) 1 d P A 2 H12' H 0.6383 0.3414 0.9250 0.050 Uiso 0.127(2) 1 d PR A 2 C13' C 0.707(2) 0.624(2) 0.9607(10) 0.040(3) Uiso 0.127(2) 1 d P A 2 H13' H 0.6958 0.5994 1.0178 0.048 Uiso 0.127(2) 1 d PR A 2 C14' C 0.7538(16) 0.799(2) 0.9388(7) 0.026(2) Uiso 0.127(2) 1 d P A 2 H14' H 0.7788 0.9036 0.9788 0.031 Uiso 0.127(2) 1 d PR A 2 C15' C 0.8207(15) 1.0118(15) 0.8249(7) 0.028(2) Uiso 0.127(2) 1 d P A 2 H15' H 0.8480 1.1139 0.8663 0.034 Uiso 0.127(2) 1 d PR A 2 C16' C 0.8260(14) 1.0341(13) 0.7425(6) 0.027(2) Uiso 0.127(2) 1 d P A 2 H16' H 0.8648 1.1567 0.7258 0.032 Uiso 0.127(2) 1 d PR A 2 C17' C 0.7834(13) 0.8837(19) 0.6796(6) 0.0161(17) Uiso 0.127(2) 1 d P A 2 C18' C 0.7336(14) 0.6979(17) 0.7004(6) 0.0233(19) Uiso 0.127(2) 1 d P A 2 C19' C 0.7263(13) 0.6704(17) 0.7940(6) 0.0163(17) Uiso 0.127(2) 1 d P A 2 C20' C 0.7655(14) 0.8257(16) 0.8489(7) 0.0235(19) Uiso 0.127(2) 1 d P 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 C1 0.0261(6) 0.0303(6) 0.0403(7) 0.0074(5) 0.0042(5) 0.0078(5) C2 0.0262(6) 0.0287(6) 0.0356(7) -0.0037(5) 0.0011(5) 0.0076(5) C3 0.0227(5) 0.0372(6) 0.0290(6) 0.0024(5) 0.0043(4) 0.0082(5) C4 0.0236(6) 0.0284(6) 0.0384(7) 0.0046(5) 0.0063(5) 0.0051(4) C5 0.0249(6) 0.0310(6) 0.0372(7) -0.0047(5) 0.0046(5) 0.0089(5) C6 0.0258(6) 0.0418(7) 0.0288(6) 0.0045(5) 0.0059(5) 0.0121(5) F1 0.0466(5) 0.0350(4) 0.0553(5) 0.0161(4) 0.0073(4) 0.0084(4) F2 0.0464(5) 0.0337(4) 0.0490(5) -0.0118(4) 0.0006(4) 0.0085(4) F3 0.0398(4) 0.0560(5) 0.0290(4) 0.0039(3) 0.0078(3) 0.0130(4) F4 0.0404(5) 0.0316(4) 0.0545(5) 0.0108(4) 0.0109(4) 0.0021(3) F5 0.0474(5) 0.0384(5) 0.0479(5) -0.0132(4) 0.0068(4) 0.0113(4) F6 0.0446(5) 0.0625(6) 0.0305(4) 0.0070(4) 0.0112(3) 0.0186(4) C7 0.0269(7) 0.0330(10) 0.0276(7) -0.0045(7) 0.0056(5) 0.0039(6) C8 0.0319(8) 0.0426(10) 0.0237(8) 0.0052(7) 0.0085(6) 0.0052(7) C9 0.0330(8) 0.0322(9) 0.0335(8) 0.0071(6) 0.0089(6) 0.0055(6) C10 0.0269(7) 0.0237(8) 0.0296(7) 0.0015(5) 0.0062(5) 0.0046(5) C11 0.0240(6) 0.0319(9) 0.0276(7) -0.0038(6) 0.0033(5) 0.0055(5) C12 0.0293(7) 0.0499(12) 0.0261(7) -0.0067(7) 0.0033(5) 0.0068(7) C13 0.0330(8) 0.0602(14) 0.0241(8) 0.0043(9) 0.0064(6) 0.0083(8) C14 0.0283(7) 0.0438(10) 0.0314(8) 0.0100(7) 0.0071(6) 0.0058(6) C15 0.0254(6) 0.0245(6) 0.0403(8) 0.0048(5) 0.0068(6) 0.0022(5) C16 0.0250(6) 0.0221(6) 0.0374(7) -0.0048(5) 0.0038(5) 0.0031(5) C17 0.0188(6) 0.0270(8) 0.0257(7) -0.0018(5) 0.0039(5) 0.0049(5) C18 0.0174(6) 0.0229(8) 0.0240(6) 0.0008(6) 0.0036(5) 0.0047(5) C19 0.0177(6) 0.0259(8) 0.0224(7) -0.0003(5) 0.0035(4) 0.0050(5) C20 0.0193(6) 0.0300(8) 0.0291(7) 0.0046(6) 0.0049(5) 0.0045(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 C1 F1 1.3421(15) . ? C1 C6 1.3820(19) . ? C1 C2 1.3826(19) . ? C2 F2 1.3386(14) . ? C2 C3 1.3825(18) . ? C3 F3 1.3402(15) . ? C3 C4 1.3851(18) . ? C4 F4 1.3410(14) . ? C4 C5 1.3819(19) . ? C5 F5 1.3441(14) . ? C5 C6 1.3820(19) . ? C6 F6 1.3389(15) . ? C7 C8 1.371(2) . ? C7 C17 1.422(2) . ? C8 C9 1.411(3) . ? C9 C10 1.373(2) . ? C10 C18 1.4185(19) . ? C11 C12 1.384(2) . ? C11 C19 1.417(2) . ? C12 C13 1.406(3) . ? C13 C14 1.372(3) . ? C14 C20 1.421(2) . ? C15 C16 1.353(2) . ? C15 C20 1.436(2) . ? C16 C17 1.439(2) . ? C17 C18 1.421(2) . ? C18 C19 1.4619(19) . ? C19 C20 1.418(2) . ? C7' C8' 1.371(17) . ? C7' C17' 1.484(16) . ? C8' C9' 1.317(18) . ? C9' C10' 1.396(17) . ? C10' C18' 1.371(15) . ? C11' C12' 1.373(17) . ? C11' C19' 1.423(16) . ? C12' C13' 1.41(2) . ? C13' C14' 1.339(18) . ? C14' C20' 1.473(16) . ? C15' C16' 1.339(14) . ? C15' C20' 1.432(14) . ? C16' C17' 1.417(14) . ? C17' C18' 1.407(16) . ? C18' C19' 1.526(14) . ? C19' C20' 1.368(15) . ? 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 C6 119.83(12) . . ? F1 C1 C2 119.77(12) . . ? C6 C1 C2 120.40(12) . . ? F2 C2 C3 119.96(12) . . ? F2 C2 C1 120.24(12) . . ? C3 C2 C1 119.79(12) . . ? F3 C3 C2 120.06(12) . . ? F3 C3 C4 120.02(12) . . ? C2 C3 C4 119.92(12) . . ? F4 C4 C5 120.05(12) . . ? F4 C4 C3 119.88(12) . . ? C5 C4 C3 120.07(12) . . ? F5 C5 C4 119.65(12) . . ? F5 C5 C6 120.27(12) . . ? C4 C5 C6 120.09(12) . . ? F6 C6 C1 120.22(12) . . ? F6 C6 C5 120.05(12) . . ? C1 C6 C5 119.74(12) . . ? C8 C7 C17 120.79(16) . . ? C7 C8 C9 119.86(14) . . ? C10 C9 C8 120.53(17) . . ? C9 C10 C18 121.12(15) . . ? C12 C11 C19 120.83(17) . . ? C11 C12 C13 120.61(17) . . ? C14 C13 C12 119.91(16) . . ? C13 C14 C20 120.63(17) . . ? C16 C15 C20 121.21(13) . . ? C15 C16 C17 121.13(12) . . ? C18 C17 C7 119.44(16) . . ? C18 C17 C16 119.67(13) . . ? C7 C17 C16 120.90(16) . . ? C10 C18 C17 118.24(13) . . ? C10 C18 C19 122.67(13) . . ? C17 C18 C19 119.09(14) . . ? C11 C19 C20 118.22(13) . . ? C11 C19 C18 122.71(14) . . ? C20 C19 C18 119.07(13) . . ? C19 C20 C14 119.78(14) . . ? C19 C20 C15 119.82(14) . . ? C14 C20 C15 120.39(16) . . ? C8' C7' C17' 115.8(12) . . ? C9' C8' C7' 126.4(13) . . ? C8' C9' C10' 119.3(13) . . ? C18' C10' C9' 119.2(13) . . ? C12' C11' C19' 120.1(11) . . ? C11' C12' C13' 116.9(14) . . ? C14' C13' C12' 125.6(14) . . ? C13' C14' C20' 117.3(12) . . ? C16' C15' C20' 117.3(9) . . ? C15' C16' C17' 123.3(10) . . ? C18' C17' C16' 121.6(9) . . ? C18' C17' C7' 116.6(10) . . ? C16' C17' C7' 121.8(12) . . ? C10' C18' C17' 122.7(10) . . ? C10' C18' C19' 121.6(10) . . ? C17' C18' C19' 115.7(9) . . ? C20' C19' C11' 122.2(9) . . ? C20' C19' C18' 117.9(11) . . ? C11' C19' C18' 119.9(9) . . ? C19' C20' C15' 124.1(10) . . ? C19' C20' C14' 117.8(10) . . ? C15' C20' C14' 118.0(10) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.320 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.045 #=========================================================================== #=========END data_(4) _database_code_CSD 175698 _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexafluorobenzene : pyrene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10,C6 F6' _chemical_formula_sum 'C22 H10 F6' _chemical_formula_weight 388.30 _ccdc_compound_id 'ZZZGKE01' _ccdc_polymorph 'possibly phase transition below 200 K' _ccdc_comments 'ZZZGKE has a==9.88,b==13.5,c==6.98 \%A, \b==113\%, sp.gr. C2(/m)' 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 'P 1 21/c 1' 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 6.9467(14) _cell_length_b 13.331(3) _cell_length_c 9.3010(19) _cell_angle_alpha 90.00 _cell_angle_beta 106.67(3) _cell_angle_gamma 90.00 _cell_volume 825.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 944 _cell_measurement_theta_min 5.13 _cell_measurement_theta_max 24.69 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4154 _exptl_absorpt_correction_T_max 0.7349 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _exptl_special_details ;The data collection nominally covered 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 (30 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 duplicate reflections. Crystals desintegrated at lower temperature, possibly due to a phase transition. ; _diffrn_ambient_temperature 200(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_decay_% 0 _diffrn_reflns_number 5231 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1882 _reflns_number_gt 1287 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _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. ; _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^)+(0.0646P)^2^+0.1656P] 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 SHELXL _refine_ls_extinction_coef 0.026(4) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1882 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6166(2) 0.57431(14) -0.3242(2) 0.0369(4) Uani 1 1 d . . . C2 C 0.7174(3) 0.55552(17) -0.1729(2) 0.0474(5) Uani 1 1 d . . . H2 H 0.7600 0.6101 -0.1056 0.038(5) Uiso 1 1 calc R . . C3 C 0.7550(3) 0.45906(18) -0.1209(2) 0.0509(6) Uani 1 1 d . . . H3 H 0.8232 0.4478 -0.0181 0.060(6) Uiso 1 1 calc R . . C4 C 0.6950(3) 0.37762(17) -0.2167(2) 0.0465(5) Uani 1 1 d . . . H4 H 0.7245 0.3115 -0.1785 0.058(6) Uiso 1 1 calc R . . C5 C 0.5925(2) 0.39145(14) -0.3672(2) 0.0365(4) Uani 1 1 d . . . C6 C 0.5517(2) 0.49249(13) -0.42307(18) 0.0297(4) Uani 1 1 d . . . C7 C 0.5765(3) 0.67347(15) -0.3842(2) 0.0435(5) Uani 1 1 d . . . H7 H 0.6213 0.7293 -0.3200 0.056(6) Uiso 1 1 calc R . . C8 C 0.5236(3) 0.31021(14) -0.4698(2) 0.0395(4) Uani 1 1 d . . . H8 H 0.5488 0.2432 -0.4346 0.050(6) Uiso 1 1 calc R . . C11 C 0.9863(3) 0.60248(14) -0.5193(2) 0.0395(4) Uani 1 1 d . . . C12 C 1.0783(3) 0.56248(15) -0.3797(2) 0.0405(5) Uani 1 1 d . . . C13 C 1.0925(3) 0.46016(15) -0.3607(2) 0.0395(4) Uani 1 1 d . . . F11 F 0.97481(19) 0.70215(9) -0.53766(15) 0.0577(4) Uani 1 1 d . . . F12 F 1.15421(19) 0.62337(10) -0.26228(13) 0.0578(4) Uani 1 1 d . . . F13 F 1.18356(17) 0.42114(10) -0.22572(12) 0.0561(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 C1 0.0302(8) 0.0428(11) 0.0406(10) -0.0050(8) 0.0144(7) -0.0019(7) C2 0.0386(10) 0.0679(15) 0.0344(10) -0.0102(9) 0.0083(8) -0.0037(9) C3 0.0419(10) 0.0747(16) 0.0336(10) 0.0040(10) 0.0069(8) -0.0016(10) C4 0.0416(10) 0.0504(12) 0.0490(11) 0.0172(10) 0.0156(9) 0.0041(9) C5 0.0296(8) 0.0413(11) 0.0412(10) 0.0030(8) 0.0145(7) 0.0002(7) C6 0.0246(7) 0.0349(9) 0.0318(8) -0.0012(7) 0.0118(6) -0.0003(6) C7 0.0414(10) 0.0378(11) 0.0536(11) -0.0085(9) 0.0174(9) -0.0025(8) C8 0.0386(9) 0.0258(9) 0.0562(12) 0.0033(8) 0.0170(8) -0.0001(7) C11 0.0371(9) 0.0355(11) 0.0499(11) -0.0008(8) 0.0190(8) -0.0017(8) C12 0.0346(9) 0.0477(12) 0.0426(10) -0.0101(9) 0.0166(8) -0.0071(8) C13 0.0314(9) 0.0506(11) 0.0383(10) 0.0058(8) 0.0127(8) 0.0025(8) F11 0.0627(7) 0.0371(7) 0.0775(9) 0.0029(6) 0.0266(7) 0.0016(5) F12 0.0615(8) 0.0619(8) 0.0507(7) -0.0191(6) 0.0172(6) -0.0159(6) F13 0.0510(7) 0.0718(9) 0.0438(7) 0.0116(6) 0.0106(5) 0.0059(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.403(3) . ? C1 C6 1.415(2) . ? C1 C7 1.431(3) . ? C2 C3 1.372(3) . ? C2 H2 0.9500 . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C8 1.432(3) . ? C5 C6 1.442(3) . ? C6 C6 1.419(3) 3_664 ? C7 C8 1.353(3) 3_664 ? C7 H7 0.9500 . ? C8 C7 1.353(3) 3_664 ? C8 H8 0.9500 . ? C11 F11 1.339(2) . ? C11 C13 1.376(3) 3_764 ? C11 C12 1.379(3) . ? C12 F12 1.341(2) . ? C12 C13 1.375(3) . ? C13 F13 1.339(2) . ? C13 C11 1.376(3) 3_764 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.27(18) . . ? C2 C1 C7 122.82(17) . . ? C6 C1 C7 117.91(16) . . ? C3 C2 C1 120.68(19) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.99(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.98(19) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C8 123.24(18) . . ? C4 C5 C6 118.55(17) . . ? C8 C5 C6 118.21(16) . . ? C1 C6 C6 121.4(2) . 3_664 ? C1 C6 C5 119.53(15) . . ? C6 C6 C5 119.03(19) 3_664 . ? C8 C7 C1 121.78(18) 3_664 . ? C8 C7 H7 119.1 3_664 . ? C1 C7 H7 119.1 . . ? C7 C8 C5 121.61(17) 3_664 . ? C7 C8 H8 119.2 3_664 . ? C5 C8 H8 119.2 . . ? F11 C11 C13 120.22(17) . 3_764 ? F11 C11 C12 119.89(17) . . ? C13 C11 C12 119.89(18) 3_764 . ? F12 C12 C13 119.94(17) . . ? F12 C12 C11 120.01(18) . . ? C13 C12 C11 120.05(16) . . ? F13 C13 C12 120.18(17) . . ? F13 C13 C11 119.76(18) . 3_764 ? C12 C13 C11 120.06(17) . 3_764 ? 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 C6 C1 C2 C3 0.7(3) . . . . ? C7 C1 C2 C3 -179.02(18) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C8 -178.66(17) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C2 C1 C6 C6 179.71(17) . . . 3_664 ? C7 C1 C6 C6 -0.6(3) . . . 3_664 ? C2 C1 C6 C5 -0.8(2) . . . . ? C7 C1 C6 C5 178.92(15) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C8 C5 C6 C1 179.57(15) . . . . ? C4 C5 C6 C6 179.56(17) . . . 3_664 ? C8 C5 C6 C6 -0.9(2) . . . 3_664 ? C2 C1 C7 C8 -179.02(16) . . . 3_664 ? C6 C1 C7 C8 1.3(2) . . . 3_664 ? C4 C5 C8 C7 179.76(16) . . . 3_664 ? C6 C5 C8 C7 0.3(2) . . . 3_664 ? F11 C11 C12 F12 0.7(2) . . . . ? C13 C11 C12 F12 -179.58(15) 3_764 . . . ? F11 C11 C12 C13 -179.23(16) . . . . ? C13 C11 C12 C13 0.5(3) 3_764 . . . ? F12 C12 C13 F13 -0.6(3) . . . . ? C11 C12 C13 F13 179.31(15) . . . . ? F12 C12 C13 C11 179.58(15) . . . 3_764 ? C11 C12 C13 C11 -0.5(3) . . . 3_764 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.296 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.041 #=========================================================================== #=========END data_(5) _database_code_CSD 175699 _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexafluorobenzene : triphenylene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12,C6 F6' _chemical_formula_sum 'C24 H12 F6' _chemical_formula_weight 414.34 _ccdc_compound_id '5' _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 'P 1 21/c 1' 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 13.935(2) _cell_length_b 7.211(2) _cell_length_c 17.370(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.55(1) _cell_angle_gamma 90.00 _cell_volume 1743.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 521 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 22.3 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of exposures; each set had a different \f and/or 2\q angles and each exposure (35 s) covered 0.3\% in \w. Crystal decay was monitored by repeating 50 initial frames at the end of data collection and comparing 66 duplicate reflections. 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_decay_% 0.1 _diffrn_reflns_number 10590 _diffrn_reflns_av_R_equivalents 0.1439 _diffrn_reflns_av_sigmaI/netI 0.1020 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3075 _reflns_number_gt 1722 _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^)+(0.0896P)^2^+6.6P] 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 3075 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1674 _refine_ls_R_factor_gt 0.1019 _refine_ls_wR_factor_ref 0.2850 _refine_ls_wR_factor_gt 0.2446 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4390(5) 0.1688(9) 0.6058(4) 0.0292(16) Uani 1 1 d . . . H1 H 0.4718 0.1809 0.5593 0.035 Uiso 1 1 d R . . C2 C 0.4827(5) 0.2252(9) 0.6732(4) 0.0335(17) Uani 1 1 d . . . H2 H 0.5456 0.2754 0.6728 0.040 Uiso 1 1 d R . . C3 C 0.4375(5) 0.2113(9) 0.7427(4) 0.0367(18) Uani 1 1 d . . . H3 H 0.4686 0.2516 0.7894 0.044 Uiso 1 1 d R . . C4 C 0.3467(5) 0.1378(9) 0.7418(4) 0.0317(16) Uani 1 1 d . . . H4 H 0.3147 0.1293 0.7888 0.038 Uiso 1 1 d R . . C5 C 0.1533(5) -0.0269(9) 0.7433(4) 0.0335(17) Uani 1 1 d . . . H5 H 0.1858 0.0053 0.7906 0.040 Uiso 1 1 d R . . C6 C 0.0610(5) -0.0969(10) 0.7433(4) 0.0379(18) Uani 1 1 d . . . H6 H 0.0300 -0.1104 0.7906 0.045 Uiso 1 1 d R . . C7 C 0.0132(5) -0.1480(9) 0.6746(5) 0.0365(18) Uani 1 1 d . . . H7 H -0.0501 -0.1970 0.6749 0.044 Uiso 1 1 d R . . C8 C 0.0580(5) -0.1271(9) 0.6062(4) 0.0338(17) Uani 1 1 d . . . H8 H 0.0248 -0.1605 0.5593 0.041 Uiso 1 1 d R . . C9 C 0.1566(5) -0.0948(9) 0.4602(4) 0.0331(17) Uani 1 1 d . . . H9 H 0.0936 -0.1449 0.4601 0.040 Uiso 1 1 d R . . C10 C 0.2011(5) -0.0802(10) 0.3920(4) 0.0382(18) Uani 1 1 d . . . H10 H 0.1684 -0.1159 0.3452 0.046 Uiso 1 1 d R . . C11 C 0.2963(5) -0.0112(9) 0.3915(4) 0.0383(18) Uani 1 1 d . . . H11 H 0.3289 -0.0034 0.3447 0.046 Uiso 1 1 d R . . C12 C 0.3405(5) 0.0443(9) 0.4600(4) 0.0343(17) Uani 1 1 d . . . H12 H 0.4037 0.0933 0.4594 0.041 Uiso 1 1 d R . . C13 C 0.3450(4) 0.0919(8) 0.6035(4) 0.0246(14) Uani 1 1 d . . . C14 C 0.2992(4) 0.0747(8) 0.6738(4) 0.0259(15) Uani 1 1 d . . . C15 C 0.1996(4) -0.0025(8) 0.6736(4) 0.0264(15) Uani 1 1 d . . . C16 C 0.1528(4) -0.0564(8) 0.6045(4) 0.0263(15) Uani 1 1 d . . . C17 C 0.2017(4) -0.0376(8) 0.5313(4) 0.0262(15) Uani 1 1 d . . . C18 C 0.2958(4) 0.0314(8) 0.5312(4) 0.0251(15) Uani 1 1 d . . . C21 C 0.2068(5) 0.4535(9) 0.4988(4) 0.0307(16) Uani 1 1 d . . . C22 C 0.2997(5) 0.5191(9) 0.4984(4) 0.0334(17) Uani 1 1 d . . . C23 C 0.3458(4) 0.5805(9) 0.5658(4) 0.0285(16) Uani 1 1 d . . . C24 C 0.3009(5) 0.5675(8) 0.6344(4) 0.0269(15) Uani 1 1 d . . . C25 C 0.2086(5) 0.4981(8) 0.6353(4) 0.0270(15) Uani 1 1 d . . . C26 C 0.1614(4) 0.4416(9) 0.5678(4) 0.0274(15) Uani 1 1 d . . . F21 F 0.1610(3) 0.3997(5) 0.4336(2) 0.0448(11) Uani 1 1 d . . . F22 F 0.3450(3) 0.5286(6) 0.4316(2) 0.0486(12) Uani 1 1 d . . . F23 F 0.4366(3) 0.6444(5) 0.5652(2) 0.0415(11) Uani 1 1 d . . . F24 F 0.3449(3) 0.6247(5) 0.7000(2) 0.0371(10) Uani 1 1 d . . . F25 F 0.1648(3) 0.4829(6) 0.7021(2) 0.0397(11) Uani 1 1 d . . . F26 F 0.0701(3) 0.3773(5) 0.5682(2) 0.0418(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(3) 0.025(3) 0.035(4) 0.004(3) 0.005(3) 0.004(3) C2 0.025(4) 0.026(4) 0.050(5) 0.002(3) -0.005(3) 0.005(3) C3 0.037(4) 0.029(4) 0.044(5) -0.006(3) -0.002(4) 0.006(3) C4 0.029(4) 0.036(4) 0.030(4) 0.000(3) 0.000(3) 0.004(3) C5 0.037(4) 0.027(4) 0.037(4) 0.000(3) 0.003(3) 0.001(3) C6 0.032(4) 0.034(4) 0.049(5) 0.009(4) 0.014(3) 0.004(3) C7 0.024(3) 0.021(3) 0.065(5) 0.005(3) 0.001(4) 0.001(3) C8 0.033(4) 0.018(3) 0.050(5) 0.003(3) 0.002(3) 0.004(3) C9 0.036(4) 0.017(3) 0.046(5) 0.002(3) -0.003(3) 0.002(3) C10 0.054(5) 0.031(4) 0.029(4) 0.000(3) -0.004(4) 0.009(3) C11 0.049(4) 0.028(4) 0.039(5) 0.001(3) 0.008(4) 0.010(3) C12 0.041(4) 0.021(3) 0.041(5) 0.002(3) 0.007(3) 0.005(3) C13 0.027(3) 0.015(3) 0.032(4) 0.002(3) 0.005(3) 0.004(3) C14 0.019(3) 0.016(3) 0.043(4) 0.001(3) -0.001(3) 0.008(3) C15 0.027(3) 0.018(3) 0.034(4) 0.000(3) 0.004(3) 0.009(3) C16 0.027(3) 0.012(3) 0.040(4) 0.002(3) 0.004(3) 0.007(3) C17 0.024(3) 0.015(3) 0.040(4) 0.000(3) 0.001(3) 0.004(3) C18 0.026(3) 0.014(3) 0.035(4) 0.003(3) 0.004(3) 0.003(3) C21 0.040(4) 0.017(3) 0.035(4) 0.001(3) -0.003(3) 0.004(3) C22 0.042(4) 0.019(3) 0.039(5) 0.002(3) 0.009(3) 0.004(3) C23 0.029(4) 0.018(3) 0.039(4) 0.004(3) 0.004(3) 0.003(3) C24 0.039(4) 0.013(3) 0.028(4) -0.003(3) -0.005(3) 0.010(3) C25 0.033(4) 0.018(3) 0.031(4) 0.002(3) 0.005(3) 0.006(3) C26 0.027(3) 0.019(3) 0.036(4) 0.001(3) 0.001(3) 0.001(3) F21 0.069(3) 0.031(2) 0.033(2) -0.0031(19) -0.009(2) 0.003(2) F22 0.070(3) 0.034(2) 0.044(3) 0.005(2) 0.018(2) 0.004(2) F23 0.028(2) 0.031(2) 0.065(3) 0.009(2) 0.0074(19) -0.0058(18) F24 0.041(2) 0.029(2) 0.040(2) -0.0010(19) -0.0048(18) 0.0026(18) F25 0.042(2) 0.039(2) 0.039(2) -0.0012(19) 0.0092(19) 0.0057(19) F26 0.033(2) 0.030(2) 0.062(3) -0.002(2) 0.0005(19) -0.0053(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.358(9) . ? C1 C13 1.420(9) . ? C2 C3 1.390(10) . ? C3 C4 1.371(9) . ? C4 C14 1.404(9) . ? C5 C6 1.382(9) . ? C5 C15 1.407(9) . ? C6 C7 1.390(10) . ? C7 C8 1.375(10) . ? C8 C16 1.418(9) . ? C9 C10 1.365(10) . ? C9 C17 1.421(9) . ? C10 C11 1.417(10) . ? C11 C12 1.375(10) . ? C12 C18 1.412(10) . ? C13 C14 1.408(9) . ? C13 C18 1.471(9) . ? C14 C15 1.496(8) . ? C15 C16 1.395(9) . ? C16 C17 1.476(9) . ? C17 C18 1.403(8) . ? C21 F21 1.333(7) . ? C21 C22 1.378(9) . ? C21 C26 1.382(10) . ? C22 F22 1.347(8) . ? C22 C23 1.383(9) . ? C23 F23 1.347(7) . ? C23 C24 1.374(9) . ? C24 F24 1.336(7) . ? C24 C25 1.380(9) . ? C25 F25 1.340(7) . ? C25 C26 1.381(9) . ? C26 F26 1.354(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C13 121.2(6) . . ? C1 C2 C3 121.6(6) . . ? C4 C3 C2 118.2(7) . . ? C3 C4 C14 122.3(7) . . ? C6 C5 C15 120.6(7) . . ? C5 C6 C7 120.5(7) . . ? C8 C7 C6 119.6(6) . . ? C7 C8 C16 121.1(7) . . ? C10 C9 C17 122.1(7) . . ? C9 C10 C11 119.6(7) . . ? C12 C11 C10 118.7(7) . . ? C11 C12 C18 122.7(7) . . ? C14 C13 C1 117.6(6) . . ? C14 C13 C18 120.1(6) . . ? C1 C13 C18 122.3(6) . . ? C4 C14 C13 119.1(6) . . ? C4 C14 C15 121.6(6) . . ? C13 C14 C15 119.2(6) . . ? C16 C15 C5 119.3(6) . . ? C16 C15 C14 120.2(6) . . ? C5 C15 C14 120.4(6) . . ? C15 C16 C8 118.9(6) . . ? C15 C16 C17 120.0(6) . . ? C8 C16 C17 121.1(6) . . ? C18 C17 C9 118.6(6) . . ? C18 C17 C16 120.1(6) . . ? C9 C17 C16 121.3(6) . . ? C17 C18 C12 118.2(6) . . ? C17 C18 C13 120.3(6) . . ? C12 C18 C13 121.4(6) . . ? F21 C21 C22 120.6(6) . . ? F21 C21 C26 119.9(6) . . ? C22 C21 C26 119.5(6) . . ? F22 C22 C21 120.0(6) . . ? F22 C22 C23 119.6(6) . . ? C21 C22 C23 120.4(6) . . ? F23 C23 C24 119.6(6) . . ? F23 C23 C22 120.3(6) . . ? C24 C23 C22 120.0(6) . . ? F24 C24 C23 120.6(6) . . ? F24 C24 C25 119.6(6) . . ? C23 C24 C25 119.7(6) . . ? F25 C25 C24 120.1(6) . . ? F25 C25 C26 119.6(6) . . ? C24 C25 C26 120.4(6) . . ? F26 C26 C25 120.6(6) . . ? F26 C26 C21 119.5(6) . . ? C25 C26 C21 119.9(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.410 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.106 #=========================================================================== #=============END