# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jin Liu' 'Kelly Jo Boarman' _publ_contact_author_name 'Dr Jin Liu' _publ_contact_author_address ; Department of Chemistry Murray State University 456 Blackburn Science Building Murray KY 42071 UNITED STATES OF AMERICA ; _publ_contact_author_email JIN.LIU@MURRAYSTATE.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Regiospecific Topochemical Reactions Controlled by Trifluoromethyl Directing Groups ; data_04143a _database_code_depnum_ccdc_archive 'CCDC 249913' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 04143a _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 F6' _chemical_formula_sum 'C18 H12 F6' _chemical_formula_weight 342.28 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3758(19) _cell_length_b 4.9215(9) _cell_length_c 15.280(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.108(2) _cell_angle_gamma 90.00 _cell_volume 745.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1824 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.43 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9395 _exptl_absorpt_correction_T_max 0.9725 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details 'Prof. Jin Liu - Murray State University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6437 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1690 _reflns_number_gt 1381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.3002P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1690 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.44690(15) 0.5985(3) 0.49487(10) 0.0325(3) Uani 1 1 d . . . H1A H 0.4136 0.6300 0.5456 0.039 Uiso 1 1 calc R . . C2 C 0.39284(16) 0.7387(3) 0.41843(10) 0.0359(4) Uani 1 1 d . . . H2A H 0.4272 0.7034 0.3684 0.043 Uiso 1 1 calc R . . C3 C 0.28488(14) 0.9433(3) 0.40377(9) 0.0300(3) Uani 1 1 d . . . C4 C 0.23913(14) 1.0924(3) 0.32148(9) 0.0283(3) Uani 1 1 d . . . C5 C 0.13662(15) 1.2835(3) 0.30883(10) 0.0346(3) Uani 1 1 d . . . H5A H 0.1073 1.3816 0.2529 0.041 Uiso 1 1 calc R . . C6 C 0.07728(15) 1.3314(4) 0.37712(11) 0.0388(4) Uani 1 1 d . . . H6A H 0.0072 1.4619 0.3683 0.047 Uiso 1 1 calc R . . C7 C 0.12038(17) 1.1882(4) 0.45861(11) 0.0403(4) Uani 1 1 d . . . H7A H 0.0800 1.2212 0.5059 0.048 Uiso 1 1 calc R . . C8 C 0.22185(17) 0.9978(3) 0.47125(10) 0.0382(4) Uani 1 1 d . . . H8A H 0.2498 0.9008 0.5274 0.046 Uiso 1 1 calc R . . C9 C 0.30258(15) 1.0525(3) 0.24610(10) 0.0335(3) Uani 1 1 d . . . F1 F 0.24877(12) 1.2150(2) 0.17399(7) 0.0536(3) Uani 1 1 d . . . F2 F 0.43524(10) 1.1023(2) 0.27247(7) 0.0486(3) Uani 1 1 d . . . F3 F 0.28783(10) 0.7983(2) 0.21219(6) 0.0427(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0337(8) 0.0293(7) 0.0316(7) -0.0011(6) 0.0050(6) 0.0001(6) C2 0.0387(8) 0.0367(8) 0.0321(7) 0.0032(6) 0.0101(6) 0.0066(6) C3 0.0293(7) 0.0284(7) 0.0297(7) 0.0005(5) 0.0048(5) -0.0008(5) C4 0.0282(7) 0.0254(7) 0.0288(6) -0.0016(5) 0.0045(5) -0.0034(5) C5 0.0337(8) 0.0299(7) 0.0350(7) 0.0010(6) 0.0021(6) 0.0020(6) C6 0.0310(8) 0.0374(9) 0.0441(8) -0.0053(7) 0.0051(6) 0.0052(6) C7 0.0401(8) 0.0447(9) 0.0390(8) -0.0050(7) 0.0160(7) 0.0021(7) C8 0.0430(9) 0.0403(9) 0.0319(7) 0.0030(6) 0.0119(6) 0.0038(7) C9 0.0363(8) 0.0307(8) 0.0322(7) 0.0037(6) 0.0081(6) -0.0001(6) F1 0.0744(8) 0.0521(6) 0.0374(5) 0.0170(4) 0.0211(5) 0.0163(5) F2 0.0396(5) 0.0581(7) 0.0529(6) -0.0022(5) 0.0209(4) -0.0103(5) F3 0.0532(6) 0.0374(5) 0.0405(5) -0.0066(4) 0.0183(4) 0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.330(2) . ? C1 C1 1.441(3) 3_666 ? C1 H1A 0.9500 . ? C2 C3 1.474(2) . ? C2 H2A 0.9500 . ? C3 C8 1.400(2) . ? C3 C4 1.4122(19) . ? C4 C5 1.390(2) . ? C4 C9 1.498(2) . ? C5 C6 1.379(2) . ? C5 H5A 0.9500 . ? C6 C7 1.386(2) . ? C6 H6A 0.9500 . ? C7 C8 1.380(2) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 F2 1.3382(18) . ? C9 F1 1.3430(17) . ? C9 F3 1.3455(18) . ? 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 C1 123.77(18) . 3_666 ? C2 C1 H1A 118.1 . . ? C1 C1 H1A 118.1 3_666 . ? C1 C2 C3 126.38(14) . . ? C1 C2 H2A 116.8 . . ? C3 C2 H2A 116.8 . . ? C8 C3 C4 116.66(13) . . ? C8 C3 C2 121.20(13) . . ? C4 C3 C2 122.13(13) . . ? C5 C4 C3 121.24(13) . . ? C5 C4 C9 118.24(12) . . ? C3 C4 C9 120.52(13) . . ? C6 C5 C4 120.27(14) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C7 119.69(15) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C8 C7 C6 120.17(15) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C3 121.97(14) . . ? C7 C8 H8A 119.0 . . ? C3 C8 H8A 119.0 . . ? F2 C9 F1 106.30(12) . . ? F2 C9 F3 106.05(12) . . ? F1 C9 F3 105.37(12) . . ? F2 C9 C4 112.97(12) . . ? F1 C9 C4 112.46(12) . . ? F3 C9 C4 113.08(12) . . ? 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 C1 C1 C2 C3 -179.66(17) 3_666 . . . ? C1 C2 C3 C8 -4.0(3) . . . . ? C1 C2 C3 C4 176.47(15) . . . . ? C8 C3 C4 C5 0.0(2) . . . . ? C2 C3 C4 C5 179.65(14) . . . . ? C8 C3 C4 C9 178.64(13) . . . . ? C2 C3 C4 C9 -1.8(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C9 C4 C5 C6 -178.59(14) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C8 -0.3(3) . . . . ? C6 C7 C8 C3 0.3(3) . . . . ? C4 C3 C8 C7 -0.2(2) . . . . ? C2 C3 C8 C7 -179.84(15) . . . . ? C5 C4 C9 F2 120.41(14) . . . . ? C3 C4 C9 F2 -58.22(18) . . . . ? C5 C4 C9 F1 0.08(19) . . . . ? C3 C4 C9 F1 -178.55(13) . . . . ? C5 C4 C9 F3 -119.12(14) . . . . ? C3 C4 C9 F3 62.25(17) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.320 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.045 data_04196a _database_code_depnum_ccdc_archive 'CCDC 249914' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 04196a _chemical_melting_point ? _chemical_formula_moiety 'C36 H24 F12' _chemical_formula_sum 'C36 H24 F12' _chemical_formula_weight 684.55 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 7.9904(9) _cell_length_b 10.0114(11) _cell_length_c 10.6547(12) _cell_angle_alpha 73.214(2) _cell_angle_beta 68.806(2) _cell_angle_gamma 84.573(2) _cell_volume 760.77(15) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1570 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.87 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9599 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details 'Prof. J. Liu - Murray State University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7718 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2700 _reflns_number_gt 2039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.2949P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2700 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.8725(3) 0.33426(19) 0.10631(19) 0.0311(4) Uani 1 1 d . . . C2 C 0.8636(3) 0.2835(2) -0.0014(2) 0.0352(5) Uani 1 1 d . . . C3 C 0.9970(3) 0.1984(2) -0.0618(2) 0.0503(6) Uani 1 1 d . . . H3A H 0.9879 0.1640 -0.1334 0.060 Uiso 1 1 calc R . . C4 C 1.1413(3) 0.1636(3) -0.0193(3) 0.0594(7) Uani 1 1 d . . . H4A H 1.2322 0.1053 -0.0612 0.071 Uiso 1 1 calc R . . C5 C 1.1541(3) 0.2134(3) 0.0846(3) 0.0552(7) Uani 1 1 d . . . H5A H 1.2540 0.1891 0.1146 0.066 Uiso 1 1 calc R . . C6 C 1.0225(3) 0.2987(2) 0.1456(2) 0.0420(5) Uani 1 1 d . . . H6A H 1.0348 0.3337 0.2157 0.050 Uiso 1 1 calc R . . C7 C 0.7298(3) 0.41819(19) 0.1789(2) 0.0323(4) Uani 1 1 d . . . H7A H 0.6672 0.4815 0.1264 0.039 Uiso 1 1 calc R . . C8 C 0.6835(3) 0.41045(19) 0.3138(2) 0.0334(5) Uani 1 1 d . . . H8A H 0.7456 0.3457 0.3657 0.040 Uiso 1 1 calc R . . C9 C 0.5423(3) 0.49505(19) 0.38955(19) 0.0325(5) Uani 1 1 d . . . H9A H 0.4851 0.5581 0.3252 0.039 Uiso 1 1 calc R . . C10 C 0.6050(3) 0.57990(19) 0.46756(19) 0.0316(4) Uani 1 1 d . . . H10A H 0.7267 0.5481 0.4696 0.038 Uiso 1 1 calc R . . C11 C 0.6046(3) 0.73674(19) 0.41638(18) 0.0321(5) Uani 1 1 d . . . C12 C 0.7310(3) 0.8216(2) 0.4217(2) 0.0411(5) Uani 1 1 d . . . C13 C 0.7284(4) 0.9659(2) 0.3699(2) 0.0541(7) Uani 1 1 d . . . H13A H 0.8167 1.0215 0.3720 0.065 Uiso 1 1 calc R . . C14 C 0.5998(4) 1.0287(2) 0.3157(2) 0.0574(7) Uani 1 1 d . . . H14A H 0.5992 1.1274 0.2804 0.069 Uiso 1 1 calc R . . C15 C 0.4714(4) 0.9478(2) 0.3130(2) 0.0500(6) Uani 1 1 d . . . H15A H 0.3806 0.9907 0.2773 0.060 Uiso 1 1 calc R . . C16 C 0.4751(3) 0.8040(2) 0.3622(2) 0.0401(5) Uani 1 1 d . . . H16A H 0.3864 0.7496 0.3589 0.048 Uiso 1 1 calc R . . C17 C 0.7087(3) 0.3162(2) -0.0512(2) 0.0459(6) Uani 1 1 d . . . F1 F 0.55018(18) 0.29502(17) 0.05310(15) 0.0633(4) Uani 1 1 d . . . F2 F 0.7062(2) 0.44870(17) -0.12288(17) 0.0791(5) Uani 1 1 d . . . F3 F 0.7027(3) 0.2386(2) -0.1318(2) 0.0925(6) Uani 1 1 d . . . C18 C 0.8670(4) 0.7595(3) 0.4869(3) 0.0596(7) Uani 1 1 d . . . F4 F 0.7932(2) 0.67473(17) 0.61634(14) 0.0710(5) Uani 1 1 d . . . F5 F 0.9892(2) 0.68134(19) 0.41440(18) 0.0765(5) Uani 1 1 d . . . F6 F 0.9620(3) 0.8550(2) 0.4993(2) 0.1015(7) 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 0.0347(11) 0.0277(10) 0.0282(10) -0.0034(8) -0.0091(8) -0.0086(8) C2 0.0380(11) 0.0362(11) 0.0287(10) -0.0092(8) -0.0071(9) -0.0051(9) C3 0.0509(14) 0.0538(14) 0.0416(13) -0.0198(11) -0.0054(11) -0.0003(11) C4 0.0475(15) 0.0562(15) 0.0575(16) -0.0161(13) 0.0000(12) 0.0080(12) C5 0.0317(12) 0.0577(15) 0.0621(16) 0.0005(12) -0.0128(11) -0.0019(11) C6 0.0384(12) 0.0464(13) 0.0410(12) -0.0054(10) -0.0165(10) -0.0094(10) C7 0.0400(11) 0.0288(10) 0.0307(10) -0.0063(8) -0.0154(9) -0.0060(8) C8 0.0465(12) 0.0256(10) 0.0317(10) -0.0068(8) -0.0180(9) -0.0030(8) C9 0.0492(12) 0.0256(10) 0.0272(10) -0.0073(8) -0.0179(9) -0.0016(8) C10 0.0406(11) 0.0289(10) 0.0296(10) -0.0093(8) -0.0158(9) -0.0010(8) C11 0.0440(11) 0.0297(10) 0.0227(9) -0.0092(8) -0.0088(8) -0.0058(8) C12 0.0490(13) 0.0441(12) 0.0282(10) -0.0122(9) -0.0056(9) -0.0152(10) C13 0.0763(17) 0.0403(13) 0.0370(12) -0.0114(10) -0.0020(12) -0.0282(12) C14 0.093(2) 0.0282(12) 0.0356(12) -0.0060(10) -0.0048(13) -0.0109(13) C15 0.0733(16) 0.0351(12) 0.0343(12) -0.0071(9) -0.0141(11) 0.0071(11) C16 0.0552(13) 0.0325(11) 0.0342(11) -0.0095(9) -0.0170(10) -0.0021(10) C17 0.0530(14) 0.0567(15) 0.0348(12) -0.0179(11) -0.0184(11) -0.0027(11) F1 0.0431(8) 0.0946(11) 0.0606(9) -0.0241(8) -0.0234(7) -0.0079(7) F2 0.0896(12) 0.0759(11) 0.0738(11) 0.0117(9) -0.0538(10) -0.0083(9) F3 0.1017(13) 0.1310(16) 0.0953(13) -0.0793(12) -0.0595(11) 0.0175(12) C18 0.0621(16) 0.0688(17) 0.0544(15) -0.0135(13) -0.0245(13) -0.0240(14) F4 0.0887(11) 0.0878(11) 0.0458(8) -0.0052(8) -0.0382(8) -0.0251(9) F5 0.0530(9) 0.1012(13) 0.0760(11) -0.0200(10) -0.0265(8) -0.0009(9) F6 0.1110(14) 0.1019(14) 0.1177(16) -0.0184(12) -0.0661(13) -0.0529(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(3) . ? C1 C2 1.408(3) . ? C1 C7 1.470(3) . ? C2 C3 1.387(3) . ? C2 C17 1.490(3) . ? C3 C4 1.366(4) . ? C3 H3A 0.9500 . ? C4 C5 1.376(4) . ? C4 H4A 0.9500 . ? C5 C6 1.383(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.328(3) . ? C7 H7A 0.9500 . ? C8 C9 1.482(3) . ? C8 H8A 0.9500 . ? C9 C10 1.566(2) . ? C9 C10 1.574(3) 2_666 ? C9 H9A 1.0000 . ? C10 C11 1.506(3) . ? C10 C9 1.574(3) 2_666 ? C10 H10A 1.0000 . ? C11 C16 1.390(3) . ? C11 C12 1.406(3) . ? C12 C13 1.390(3) . ? C12 C18 1.489(4) . ? C13 C14 1.371(4) . ? C13 H13A 0.9500 . ? C14 C15 1.380(4) . ? C14 H14A 0.9500 . ? C15 C16 1.383(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 F3 1.328(3) . ? C17 F2 1.328(3) . ? C17 F1 1.334(3) . ? C18 F6 1.338(3) . ? C18 F4 1.342(3) . ? C18 F5 1.350(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.06(18) . . ? C6 C1 C7 120.06(18) . . ? C2 C1 C7 122.86(17) . . ? C3 C2 C1 120.82(19) . . ? C3 C2 C17 118.01(19) . . ? C1 C2 C17 121.15(18) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C1 121.4(2) . . ? C5 C6 H6A 119.3 . . ? C1 C6 H6A 119.3 . . ? C8 C7 C1 123.68(18) . . ? C8 C7 H7A 118.2 . . ? C1 C7 H7A 118.2 . . ? C7 C8 C9 125.02(18) . . ? C7 C8 H8A 117.5 . . ? C9 C8 H8A 117.5 . . ? C8 C9 C10 115.05(17) . . ? C8 C9 C10 119.25(15) . 2_666 ? C10 C9 C10 89.46(14) . 2_666 ? C8 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 2_666 . ? C11 C10 C9 117.69(15) . . ? C11 C10 C9 118.74(16) . 2_666 ? C9 C10 C9 90.54(14) . 2_666 ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 2_666 . ? C16 C11 C12 116.98(18) . . ? C16 C11 C10 120.39(17) . . ? C12 C11 C10 122.62(19) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 C18 118.5(2) . . ? C11 C12 C18 120.8(2) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C15 C16 C11 122.0(2) . . ? C15 C16 H16A 119.0 . . ? C11 C16 H16A 119.0 . . ? F3 C17 F2 107.04(19) . . ? F3 C17 F1 104.98(19) . . ? F2 C17 F1 104.7(2) . . ? F3 C17 C2 113.26(19) . . ? F2 C17 C2 113.16(19) . . ? F1 C17 C2 112.99(17) . . ? F6 C18 F4 105.9(2) . . ? F6 C18 F5 105.6(2) . . ? F4 C18 F5 105.4(2) . . ? F6 C18 C12 113.2(2) . . ? F4 C18 C12 112.6(2) . . ? F5 C18 C12 113.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.8(3) . . . . ? C7 C1 C2 C3 -176.51(18) . . . . ? C6 C1 C2 C17 -179.81(19) . . . . ? C7 C1 C2 C17 1.8(3) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C17 C2 C3 C4 -179.3(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C4 C5 C6 C1 1.3(3) . . . . ? C2 C1 C6 C5 -2.0(3) . . . . ? C7 C1 C6 C5 176.36(18) . . . . ? C6 C1 C7 C8 -33.3(3) . . . . ? C2 C1 C7 C8 145.0(2) . . . . ? C1 C7 C8 C9 179.02(17) . . . . ? C7 C8 C9 C10 -125.1(2) . . . . ? C7 C8 C9 C10 130.4(2) . . . 2_666 ? C8 C9 C10 C11 114.43(19) . . . . ? C10 C9 C10 C11 -123.2(2) 2_666 . . . ? C8 C9 C10 C9 -122.35(19) . . . 2_666 ? C10 C9 C10 C9 0.0 2_666 . . 2_666 ? C9 C10 C11 C16 33.7(3) . . . . ? C9 C10 C11 C16 -73.8(2) 2_666 . . . ? C9 C10 C11 C12 -146.96(18) . . . . ? C9 C10 C11 C12 105.6(2) 2_666 . . . ? C16 C11 C12 C13 -2.3(3) . . . . ? C10 C11 C12 C13 178.29(19) . . . . ? C16 C11 C12 C18 175.79(19) . . . . ? C10 C11 C12 C18 -3.6(3) . . . . ? C11 C12 C13 C14 1.7(3) . . . . ? C18 C12 C13 C14 -176.4(2) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C16 -1.2(3) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 1.2(3) . . . . ? C10 C11 C16 C15 -179.37(19) . . . . ? C3 C2 C17 F3 11.2(3) . . . . ? C1 C2 C17 F3 -167.18(19) . . . . ? C3 C2 C17 F2 -110.9(2) . . . . ? C1 C2 C17 F2 70.8(2) . . . . ? C3 C2 C17 F1 130.4(2) . . . . ? C1 C2 C17 F1 -48.0(3) . . . . ? C13 C12 C18 F6 6.1(3) . . . . ? C11 C12 C18 F6 -172.1(2) . . . . ? C13 C12 C18 F4 126.2(2) . . . . ? C11 C12 C18 F4 -51.9(3) . . . . ? C13 C12 C18 F5 -114.2(2) . . . . ? C11 C12 C18 F5 67.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.252 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.045