Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name T.B.Marder A.S.Batsanov J.C.Collings J.A.K.Howard P.S.Smith D.Yufit _publ_contact_author_name 'Prof Todd B. Marder' _publ_contact_author_address ; Department of Chemistry University of Durham South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email TODD.MARDER@DURHAM.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Arene-Perfluoroarene Interactions in Crystal Engineering 10: Crystal Structures of 1:1 Complexes of Octafluoronaphthalene with Biphenyl and Biphenylene ; #====================================================================== data_(1) _database_code_depnum_ccdc_archive 'CCDC 226523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; octafluoronaphthalene : biphenyl, 1:1 complex ; _chemical_name_common ? _chemical_melting_point '96--98 \% C' _chemical_formula_moiety 'C12 H10,C10 F8' _chemical_formula_sum 'C22 H10 F8' _chemical_formula_weight 426.30 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 21/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 7.3564(2) _cell_length_b 6.2253(2) _cell_length_c 18.6804(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.946(1) _cell_angle_gamma 90.00 _cell_volume 847.27(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3864 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 30.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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_reflns_number 8680 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 30.27 _reflns_number_total 2351 _reflns_number_gt 1858 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'SMART version 5.054 (Bruker, 1998)' _computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0600P)^2^+0.3000P] 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 2351 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.17125(13) 0.16902(14) 1.16989(5) 0.0323(2) Uani 1 1 d . . . F2 F 0.17830(11) 0.06556(12) 1.03048(5) 0.0269(2) Uani 1 1 d . . . F3 F 0.09522(12) 0.16125(13) 0.89489(5) 0.0279(2) Uani 1 1 d . . . F4 F -0.04130(13) 0.44713(15) 0.79329(4) 0.0333(2) Uani 1 1 d . . . C1 C 0.10585(19) 0.3066(2) 1.11725(7) 0.0233(3) Uani 1 1 d . . . C2 C 0.10653(18) 0.2556(2) 1.04645(7) 0.0201(3) Uani 1 1 d . . . C3 C 0.03553(17) 0.39828(19) 0.99016(7) 0.0182(3) Uani 1 1 d . . . C4 C 0.03097(18) 0.3507(2) 0.91577(7) 0.0207(3) Uani 1 1 d . . . C5 C -0.03714(19) 0.4940(2) 0.86363(7) 0.0233(3) Uani 1 1 d . . . C6 C 0.01606(17) 0.0120(2) 0.54034(7) 0.0216(3) Uani 1 1 d . . . C7 C -0.0210(2) -0.1566(2) 0.58601(8) 0.0289(3) Uani 1 1 d . . . C8 C 0.0071(3) -0.1335(3) 0.66100(9) 0.0361(4) Uani 1 1 d . . . C9 C 0.0731(2) 0.0579(3) 0.69224(8) 0.0354(4) Uani 1 1 d . . . C10 C 0.1120(2) 0.2261(3) 0.64804(9) 0.0347(4) Uani 1 1 d . . . C11 C 0.0845(2) 0.2041(2) 0.57328(8) 0.0279(3) Uani 1 1 d . . . H7 H -0.064(3) -0.287(3) 0.5658(10) 0.040(5) Uiso 1 1 d . . . H8 H -0.017(3) -0.252(4) 0.6917(11) 0.044(6) Uiso 1 1 d . . . H9 H 0.091(3) 0.072(3) 0.7442(11) 0.037(5) Uiso 1 1 d . . . H10 H 0.159(3) 0.359(3) 0.6717(10) 0.043(5) Uiso 1 1 d . . . H11 H 0.108(3) 0.325(3) 0.5437(10) 0.032(5) 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 0.0366(5) 0.0298(4) 0.0279(4) 0.0098(3) -0.0043(4) -0.0022(4) F2 0.0261(4) 0.0176(4) 0.0366(5) -0.0001(3) 0.0030(3) 0.0035(3) F3 0.0340(5) 0.0208(4) 0.0306(4) -0.0080(3) 0.0098(4) -0.0012(3) F4 0.0437(5) 0.0382(5) 0.0182(4) -0.0046(4) 0.0046(4) -0.0069(4) C1 0.0219(6) 0.0231(6) 0.0238(6) 0.0056(5) -0.0010(5) -0.0042(5) C2 0.0178(6) 0.0156(5) 0.0266(7) 0.0000(5) 0.0024(5) -0.0010(4) C3 0.0171(6) 0.0164(6) 0.0215(6) -0.0009(5) 0.0039(5) -0.0032(5) C4 0.0205(6) 0.0181(6) 0.0243(6) -0.0042(5) 0.0058(5) -0.0034(5) C5 0.0250(7) 0.0265(6) 0.0185(6) -0.0025(5) 0.0030(5) -0.0077(5) C6 0.0164(6) 0.0220(6) 0.0265(7) -0.0002(5) 0.0033(5) 0.0041(5) C7 0.0335(8) 0.0227(7) 0.0303(7) 0.0013(6) 0.0042(6) 0.0011(6) C8 0.0447(10) 0.0346(8) 0.0300(8) 0.0075(6) 0.0081(7) 0.0084(7) C9 0.0381(9) 0.0428(9) 0.0246(7) -0.0022(6) 0.0017(6) 0.0132(7) C10 0.0335(8) 0.0347(8) 0.0350(8) -0.0107(7) 0.0019(6) 0.0024(7) C11 0.0270(7) 0.0253(7) 0.0317(8) -0.0036(6) 0.0050(6) -0.0011(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 F1 C1 1.3422(16) . ? F2 C2 1.3457(14) . ? F3 C4 1.3481(15) . ? F4 C5 1.3422(15) . ? C1 C2 1.3609(19) . ? C1 C5 1.4050(19) 3_567 ? C2 C3 1.4198(18) . ? C3 C4 1.4167(17) . ? C3 C3 1.437(2) 3_567 ? C4 C5 1.364(2) . ? C5 C1 1.4050(19) 3_567 ? C6 C7 1.403(2) . ? C6 C11 1.4055(19) . ? C6 C6 1.501(3) 3_556 ? C7 C8 1.395(2) . ? C8 C9 1.385(3) . ? C9 C10 1.388(3) . ? C10 C11 1.390(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 120.92(13) . . ? F1 C1 C5 118.87(12) . 3_567 ? C2 C1 C5 120.20(12) . 3_567 ? F2 C2 C1 118.36(12) . . ? F2 C2 C3 120.08(11) . . ? C1 C2 C3 121.56(12) . . ? C4 C3 C2 123.51(11) . . ? C4 C3 C3 118.36(14) . 3_567 ? C2 C3 C3 118.13(14) . 3_567 ? F3 C4 C5 118.31(12) . . ? F3 C4 C3 120.34(12) . . ? C5 C4 C3 121.35(12) . . ? F4 C5 C4 120.90(12) . . ? F4 C5 C1 118.71(12) . 3_567 ? C4 C5 C1 120.39(12) . 3_567 ? C7 C6 C11 117.26(13) . . ? C7 C6 C6 121.29(15) . 3_556 ? C11 C6 C6 121.45(15) . 3_556 ? C8 C7 C6 121.30(14) . . ? C9 C8 C7 120.42(15) . . ? C8 C9 C10 119.19(15) . . ? C9 C10 C11 120.65(15) . . ? C10 C11 C6 121.18(14) . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 30.27 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.350 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.050 #==============================================END data_(2) _database_code_depnum_ccdc_archive 'CCDC 226524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; octafluoronaphthalene : biphenylene, 1:1 complex ; _chemical_name_common ? _chemical_melting_point '147--149 \% C' _chemical_formula_moiety 'C10 F8,C12 H8' _chemical_formula_sum 'C22 H8 F8' _chemical_formula_weight 424.28 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 6.446(1) _cell_length_b 7.142(1) _cell_length_c 9.751(2) _cell_angle_alpha 74.46(2) _cell_angle_beta 71.53(2) _cell_angle_gamma 85.97(2) _cell_volume 410.17(12) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 486 _cell_measurement_theta_min 10.16 _cell_measurement_theta_max 26.85 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Five sets of \w scans, each set at different \f and/or 2\q angles, each scan of 0.3\% in \w (exposure time 10 s), nominally covered full sphere of reciprocal space. Crystal to detector distance 4.42 cm. Crystal decay was monitored by repeating the first 50 scans at the end of the experiment and comparing the duplicate reflections. ; _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_reflns_number 3845 _diffrn_reflns_av_R_equivalents 0.1087 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1437 _reflns_number_gt 1101 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'SMART version 5.054 (Bruker, 1998)' _computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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^)+(0.0542P)^2^+0.1761P] 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 1437 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.2730(2) 0.2075(2) 0.27443(17) 0.0235(4) Uani 1 1 d . . . C1 C 0.4392(4) 0.1226(4) 0.3233(3) 0.0189(6) Uani 1 1 d . . . F2 F 0.6592(2) 0.1823(2) 0.07168(17) 0.0270(4) Uani 1 1 d . . . C2 C 0.6355(4) 0.1111(4) 0.2176(3) 0.0190(6) Uani 1 1 d . . . F3 F 1.0031(2) 0.0110(2) 0.15594(18) 0.0249(4) Uani 1 1 d . . . C3 C 0.8129(4) 0.0204(4) 0.2616(3) 0.0194(6) Uani 1 1 d . . . F4 F 0.9631(2) -0.1490(2) 0.44507(18) 0.0224(4) Uani 1 1 d . . . C4 C 0.7899(4) -0.0581(4) 0.4086(3) 0.0176(6) Uani 1 1 d . . . C5 C 0.5908(4) -0.0473(4) 0.5231(3) 0.0171(6) Uani 1 1 d . . . C6 C 0.4668(4) 0.6420(4) 0.2564(3) 0.0219(6) Uani 1 1 d . . . H6 H 0.345(5) 0.686(5) 0.227(4) 0.034(9) Uiso 1 1 d . . . C7 C 0.6712(5) 0.6459(4) 0.1431(3) 0.0268(7) Uani 1 1 d . . . H7 H 0.664(5) 0.699(5) 0.036(4) 0.039(9) Uiso 1 1 d . . . C8 C 0.8581(4) 0.5752(4) 0.1783(3) 0.0249(6) Uani 1 1 d . . . H8 H 0.997(5) 0.581(5) 0.095(4) 0.030(8) Uiso 1 1 d . . . C9 C 0.8589(4) 0.4937(4) 0.3272(3) 0.0214(6) Uani 1 1 d . . . H9 H 0.987(5) 0.450(4) 0.348(3) 0.024(8) Uiso 1 1 d . . . C10 C 0.6595(4) 0.4895(4) 0.4356(3) 0.0178(6) Uani 1 1 d . . . C11 C 0.4675(4) 0.5635(4) 0.3994(3) 0.0182(6) 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 F1 0.0165(8) 0.0274(9) 0.0279(9) -0.0046(7) -0.0119(7) 0.0054(6) C1 0.0145(12) 0.0173(13) 0.0266(15) -0.0064(11) -0.0087(11) 0.0024(10) F2 0.0224(8) 0.0352(9) 0.0200(9) -0.0028(7) -0.0058(7) -0.0001(7) C2 0.0198(13) 0.0181(13) 0.0184(14) -0.0022(11) -0.0064(11) -0.0024(10) F3 0.0127(7) 0.0332(9) 0.0252(9) -0.0087(7) 0.0000(6) 0.0006(6) C3 0.0111(12) 0.0202(14) 0.0261(16) -0.0102(12) -0.0007(11) -0.0028(10) F4 0.0121(7) 0.0254(9) 0.0315(9) -0.0093(7) -0.0088(6) 0.0050(6) C4 0.0131(12) 0.0159(13) 0.0272(15) -0.0090(11) -0.0086(11) 0.0035(10) C5 0.0140(13) 0.0137(12) 0.0239(15) -0.0062(11) -0.0053(11) 0.0007(10) C6 0.0179(13) 0.0215(14) 0.0285(16) -0.0059(12) -0.0105(12) 0.0003(11) C7 0.0294(15) 0.0254(15) 0.0232(16) -0.0040(13) -0.0062(13) -0.0034(12) C8 0.0194(14) 0.0238(14) 0.0267(16) -0.0076(12) 0.0012(12) -0.0036(11) C9 0.0134(13) 0.0170(13) 0.0314(16) -0.0064(12) -0.0040(11) 0.0018(10) C10 0.0154(12) 0.0154(13) 0.0233(14) -0.0054(11) -0.0067(10) 0.0004(10) C11 0.0126(12) 0.0142(12) 0.0260(15) -0.0053(11) -0.0033(11) 0.0002(10) _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 1.349(3) . ? C1 C2 1.369(4) . ? C1 C5 1.403(4) 2_656 ? F2 C2 1.339(3) . ? C2 C3 1.403(4) . ? F3 C3 1.339(3) . ? C3 C4 1.356(4) . ? F4 C4 1.349(3) . ? C4 C5 1.423(4) . ? C5 C1 1.403(4) 2_656 ? C5 C5 1.445(5) 2_656 ? C6 C11 1.358(4) . ? C6 C7 1.423(4) . ? C6 H6 0.93(3) . ? C7 C8 1.382(4) . ? C7 H7 1.03(4) . ? C8 C9 1.413(4) . ? C8 H8 0.99(3) . ? C9 C10 1.377(4) . ? C9 H9 0.93(3) . ? C10 C11 1.421(3) . ? C10 C11 1.511(4) 2_666 ? C11 C10 1.511(4) 2_666 ? 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 117.5(2) . . ? F1 C1 C5 120.8(2) . 2_656 ? C2 C1 C5 121.8(2) . 2_656 ? F2 C2 C1 120.6(2) . . ? F2 C2 C3 119.3(2) . . ? C1 C2 C3 120.0(2) . . ? F3 C3 C4 120.9(2) . . ? F3 C3 C2 118.9(2) . . ? C4 C3 C2 120.2(2) . . ? F4 C4 C3 118.0(2) . . ? F4 C4 C5 120.0(2) . . ? C3 C4 C5 122.0(2) . . ? C1 C5 C4 124.1(2) 2_656 . ? C1 C5 C5 118.5(3) 2_656 2_656 ? C4 C5 C5 117.4(3) . 2_656 ? C11 C6 C7 115.9(2) . . ? C11 C6 H6 126(2) . . ? C7 C6 H6 118(2) . . ? C8 C7 C6 121.4(3) . . ? C8 C7 H7 124.3(18) . . ? C6 C7 H7 114.3(18) . . ? C7 C8 C9 122.6(3) . . ? C7 C8 H8 118.6(18) . . ? C9 C8 H8 118.7(18) . . ? C10 C9 C8 115.3(2) . . ? C10 C9 H9 123.7(19) . . ? C8 C9 H9 121.0(19) . . ? C9 C10 C11 122.0(3) . . ? C9 C10 C11 147.3(2) . 2_666 ? C11 C10 C11 90.7(2) . 2_666 ? C6 C11 C10 122.7(2) . . ? C6 C11 C10 148.0(2) . 2_666 ? C10 C11 C10 89.3(2) . 2_666 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.067 #============================================END