# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_User-defined _database_code_depnum_ccdc_archive 'CCDC 924504' #TrackingRef '17755_web_deposit_cif_file_0_TakashiYamazaki_1360897912.Comp.3j.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H12 F6' _chemical_formula_moiety 'C24 H12 F6' _chemical_formula_weight 414.35 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.624(3) _cell_length_b 9.777(3) _cell_length_c 10.267(3) _cell_angle_alpha 89.282(7) _cell_angle_beta 73.950(6) _cell_angle_gamma 86.894(6) _cell_volume 927.0(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5018 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 27.65 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.070 _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420.00 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.991 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.849 _diffrn_reflns_number 9150 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4231 _reflns_number_gt 1642 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1660 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4231 _refine_ls_number_parameters 283 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0009Fo^2^ + 1.1800\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.737 _refine_diff_density_min -0.653 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.2345(2) 0.8260(3) 0.31496(19) 0.0959(8) Uani 1.0 2 d . . . F2 F 0.3859(3) 0.8791(3) 0.95441(19) 0.1049(9) Uani 1.0 2 d . . . F3 F 0.4339(3) 0.9233(3) 0.24513(19) 0.0977(8) Uani 1.0 2 d . . . F4 F 0.4292(3) 0.7069(2) 0.25355(19) 0.0943(8) Uani 1.0 2 d . . . F7 F 0.3594(3) 0.6693(3) 0.9297(2) 0.1296(10) Uani 1.0 2 d . . . F8 F 0.1814(3) 0.8088(3) 0.9564(2) 0.1189(9) Uani 1.0 2 d . . . C1 C 0.3817(3) 0.8281(3) 0.4643(3) 0.0559(10) Uani 1.0 2 d . . . C2 C 0.4807(3) 0.7413(3) 0.5107(3) 0.0553(10) Uani 1.0 2 d . . . C7 C 0.5969(4) 0.6620(3) 0.4227(4) 0.0639(11) Uani 1.0 2 d . . . C8 C 0.3705(4) 0.8205(4) 0.3216(4) 0.0667(12) Uani 1.0 2 d . . . C9 C 0.2901(3) 0.9246(3) 0.5513(4) 0.0601(11) Uani 1.0 2 d . . . C11 C 0.2767(4) 0.9194(4) 0.6941(4) 0.0641(11) Uani 1.0 2 d . . . C12 C 0.3572(4) 0.8152(4) 0.7426(3) 0.0640(11) Uani 1.0 2 d . . . C13 C 0.9123(4) 0.4462(4) 0.3023(4) 0.0733(12) Uani 1.0 2 d . . . C14 C 0.4675(4) 0.7364(3) 0.6539(3) 0.0602(11) Uani 1.0 2 d . . . C15 C 0.8132(4) 0.5081(4) 0.3767(4) 0.0730(12) Uani 1.0 2 d . . . C16 C 1.0328(4) 0.3725(4) 0.2113(4) 0.0653(12) Uani 1.0 2 d . . . C18 C 0.6945(4) 0.5832(4) 0.4685(4) 0.0661(12) Uani 1.0 2 d . . . C19 C 0.5735(4) 0.6535(4) 0.6966(4) 0.0757(13) Uani 1.0 2 d . . . C20 C 0.3217(5) 0.7946(5) 0.8940(4) 0.0840(15) Uani 1.0 2 d . . . C21 C 1.0630(4) 0.2357(4) 0.2323(4) 0.0710(12) Uani 1.0 2 d . . . C22 C 1.1761(4) 0.1666(4) 0.1433(4) 0.0794(13) Uani 1.0 2 d . . . C23 C 0.2071(4) 1.0317(4) 0.5049(4) 0.0731(12) Uani 1.0 2 d . . . C24 C 0.1829(4) 1.0214(4) 0.7792(4) 0.0813(13) Uani 1.0 2 d . . . C25 C 0.6808(4) 0.5804(4) 0.6078(4) 0.0768(13) Uani 1.0 2 d . . . C26 C 0.1222(4) 1.1246(4) 0.5895(5) 0.0824(14) Uani 1.0 2 d . . . C27 C 1.2631(4) 0.2304(5) 0.0345(4) 0.0855(15) Uani 1.0 2 d . . . C28 C 0.1103(4) 1.1199(4) 0.7279(5) 0.0860(15) Uani 1.0 2 d . . . C29 C 1.1201(4) 0.4370(4) 0.1004(4) 0.0861(14) Uani 1.0 2 d . . . C30 C 1.2343(5) 0.3658(5) 0.0125(4) 0.0945(15) Uani 1.0 2 d . . . H1 H 0.6059 0.6638 0.3301 0.0754 Uiso 1.0 2 calc R . . H2 H 0.5709 0.6469 0.7877 0.0920 Uiso 1.0 2 calc R . . H3 H 1.0055 0.1958 0.3099 0.0840 Uiso 1.0 2 calc R . . H4 H 1.1954 0.0750 0.1607 0.0959 Uiso 1.0 2 calc R . . H5 H 0.2154 1.0419 0.4129 0.0854 Uiso 1.0 2 calc R . . H6 H 0.1809 1.0274 0.8701 0.0940 Uiso 1.0 2 calc R . . H7 H 0.7486 0.5301 0.6407 0.0947 Uiso 1.0 2 calc R . . H8 H 0.0638 1.1849 0.5543 0.0967 Uiso 1.0 2 calc R . . H9 H 1.3358 0.1807 -0.0284 0.1004 Uiso 1.0 2 calc R . . H10 H 0.0512 1.1897 0.7790 0.0988 Uiso 1.0 2 calc R . . H11 H 1.0996 0.5283 0.0829 0.1003 Uiso 1.0 2 calc R . . H12 H 1.2961 0.4125 -0.0577 0.1073 Uiso 1.0 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0667(14) 0.1376(19) 0.0890(15) -0.0014(13) -0.0309(11) -0.0182(13) F2 0.1277(19) 0.1237(19) 0.0728(14) -0.0224(16) -0.0405(13) -0.0096(13) F3 0.1090(17) 0.1094(17) 0.0712(14) -0.0238(14) -0.0165(12) 0.0212(12) F4 0.1112(17) 0.0996(16) 0.0767(13) 0.0217(13) -0.0379(12) -0.0241(12) F7 0.178(3) 0.0977(18) 0.0817(16) 0.0095(17) 0.0120(15) 0.0217(14) F8 0.0887(17) 0.178(3) 0.0736(14) -0.0141(16) 0.0058(12) 0.0095(14) C1 0.0493(19) 0.062(2) 0.052(2) -0.0115(17) -0.0060(15) 0.0012(16) C2 0.0507(19) 0.0583(19) 0.055(2) -0.0109(16) -0.0089(16) -0.0021(16) C7 0.057(2) 0.070(3) 0.062(3) -0.0080(18) -0.0105(17) -0.0047(18) C8 0.058(3) 0.073(3) 0.065(3) -0.0017(19) -0.0105(17) -0.004(2) C9 0.0478(19) 0.060(2) 0.070(3) -0.0130(17) -0.0109(16) -0.0052(18) C11 0.057(2) 0.066(3) 0.065(3) -0.0149(18) -0.0078(17) -0.0101(19) C12 0.068(3) 0.070(3) 0.053(3) -0.0182(19) -0.0100(18) -0.0067(18) C13 0.060(3) 0.074(3) 0.087(3) -0.000(2) -0.023(2) -0.008(2) C14 0.057(2) 0.063(2) 0.061(3) -0.0144(17) -0.0146(17) -0.0001(17) C15 0.060(3) 0.075(3) 0.085(3) -0.006(2) -0.021(2) -0.006(2) C16 0.059(3) 0.066(3) 0.072(3) 0.0032(18) -0.0206(18) -0.0061(19) C18 0.057(3) 0.068(3) 0.073(3) -0.0101(18) -0.0160(18) -0.0052(18) C19 0.081(3) 0.083(3) 0.067(3) -0.010(3) -0.025(2) 0.001(2) C20 0.093(3) 0.083(3) 0.071(3) -0.008(3) -0.012(3) -0.005(3) C21 0.062(3) 0.074(3) 0.075(3) -0.0035(19) -0.0141(19) -0.0012(19) C22 0.083(3) 0.069(3) 0.088(3) 0.005(3) -0.027(3) -0.005(3) C23 0.062(3) 0.074(3) 0.078(3) -0.0049(19) -0.0104(19) -0.002(2) C24 0.073(3) 0.083(3) 0.079(3) -0.009(2) -0.005(2) -0.025(3) C25 0.072(3) 0.078(3) 0.087(3) -0.003(2) -0.033(2) -0.001(2) C26 0.064(3) 0.075(3) 0.103(4) 0.006(2) -0.016(2) -0.012(3) C27 0.076(3) 0.089(3) 0.086(3) 0.012(3) -0.015(3) -0.027(3) C28 0.072(3) 0.071(3) 0.105(4) 0.005(2) -0.008(3) -0.025(3) C29 0.099(3) 0.067(3) 0.085(3) 0.003(3) -0.014(3) 0.009(3) C30 0.088(3) 0.092(4) 0.088(3) 0.000(3) 0.001(3) -0.007(3) #============================================================================== _computing_data_collection 'CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Auto 2.0 r1' _computing_data_reduction 'CrystalClear-SM Auto 2.0 r1' _computing_structure_solution 'Superflip (Palatinus, et al., 2007)' _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C8 1.328(5) yes . . F2 C20 1.315(6) yes . . F3 C8 1.335(4) yes . . F4 C8 1.332(4) yes . . F7 C20 1.335(5) yes . . F8 C20 1.325(5) yes . . C1 C2 1.416(5) yes . . C1 C8 1.502(5) yes . . C1 C9 1.401(4) yes . . C2 C7 1.426(4) yes . . C2 C14 1.441(5) yes . . C7 C18 1.362(5) yes . . C9 C11 1.436(5) yes . . C9 C23 1.439(5) yes . . C11 C12 1.415(5) yes . . C11 C24 1.435(5) yes . . C12 C14 1.395(4) yes . . C12 C20 1.510(5) yes . . C13 C15 1.186(5) yes . . C13 C16 1.436(5) yes . . C14 C19 1.428(5) yes . . C15 C18 1.436(5) yes . . C16 C21 1.381(5) yes . . C16 C29 1.382(5) yes . . C18 C25 1.399(6) yes . . C19 C25 1.352(5) yes . . C21 C22 1.365(5) yes . . C22 C27 1.364(5) yes . . C23 C26 1.339(5) yes . . C24 C28 1.346(6) yes . . C26 C28 1.394(7) yes . . C27 C30 1.367(6) yes . . C29 C30 1.375(5) yes . . C7 H1 0.930 no . . C19 H2 0.930 no . . C21 H3 0.930 no . . C22 H4 0.930 no . . C23 H5 0.930 no . . C24 H6 0.930 no . . C25 H7 0.930 no . . C26 H8 0.930 no . . C27 H9 0.930 no . . C28 H10 0.930 no . . C29 H11 0.930 no . . C30 H12 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C8 121.8(3) yes . . . C2 C1 C9 120.6(3) yes . . . C8 C1 C9 117.6(3) yes . . . C1 C2 C7 123.5(3) yes . . . C1 C2 C14 118.6(3) yes . . . C7 C2 C14 117.8(3) yes . . . C2 C7 C18 122.8(3) yes . . . F1 C8 F3 106.0(3) yes . . . F1 C8 F4 104.0(3) yes . . . F1 C8 C1 112.8(3) yes . . . F3 C8 F4 105.3(3) yes . . . F3 C8 C1 112.3(3) yes . . . F4 C8 C1 115.5(3) yes . . . C1 C9 C11 119.8(3) yes . . . C1 C9 C23 123.1(3) yes . . . C11 C9 C23 117.1(3) yes . . . C9 C11 C12 118.4(3) yes . . . C9 C11 C24 117.9(3) yes . . . C12 C11 C24 123.8(4) yes . . . C11 C12 C14 121.1(3) yes . . . C11 C12 C20 117.7(3) yes . . . C14 C12 C20 121.2(4) yes . . . C15 C13 C16 179.4(4) yes . . . C2 C14 C12 119.4(3) yes . . . C2 C14 C19 117.2(3) yes . . . C12 C14 C19 123.4(3) yes . . . C13 C15 C18 179.0(5) yes . . . C13 C16 C21 120.7(3) yes . . . C13 C16 C29 120.7(4) yes . . . C21 C16 C29 118.6(3) yes . . . C7 C18 C15 121.4(4) yes . . . C7 C18 C25 118.7(3) yes . . . C15 C18 C25 119.9(4) yes . . . C14 C19 C25 122.0(4) yes . . . F2 C20 F7 105.4(4) yes . . . F2 C20 F8 106.4(3) yes . . . F2 C20 C12 113.3(4) yes . . . F7 C20 F8 103.6(3) yes . . . F7 C20 C12 113.7(3) yes . . . F8 C20 C12 113.6(4) yes . . . C16 C21 C22 119.9(3) yes . . . C21 C22 C27 121.4(4) yes . . . C9 C23 C26 122.1(4) yes . . . C11 C24 C28 121.6(4) yes . . . C18 C25 C19 121.5(4) yes . . . C23 C26 C28 120.6(4) yes . . . C22 C27 C30 119.3(4) yes . . . C24 C28 C26 120.7(4) yes . . . C16 C29 C30 120.6(4) yes . . . C27 C30 C29 120.1(4) yes . . . C2 C7 H1 118.494 no . . . C18 C7 H1 118.699 no . . . C14 C19 H2 121.101 no . . . C25 C19 H2 116.928 no . . . C16 C21 H3 116.988 no . . . C22 C21 H3 123.061 no . . . C21 C22 H4 118.229 no . . . C27 C22 H4 120.287 no . . . C9 C23 H5 120.383 no . . . C26 C23 H5 117.367 no . . . C11 C24 H6 119.775 no . . . C28 C24 H6 118.142 no . . . C18 C25 H7 120.004 no . . . C19 C25 H7 118.448 no . . . C23 C26 H8 117.558 no . . . C28 C26 H8 121.435 no . . . C22 C27 H9 120.421 no . . . C30 C27 H9 120.066 no . . . C24 C28 H10 124.318 no . . . C26 C28 H10 115.008 no . . . C16 C29 H11 119.901 no . . . C30 C29 H11 119.482 no . . . C27 C30 H12 120.381 no . . . C29 C30 H12 119.272 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C8 F1 136.4(3) no . . . . C2 C1 C8 F3 -103.9(4) no . . . . C2 C1 C8 F4 16.9(5) no . . . . C8 C1 C2 C7 13.8(5) no . . . . C8 C1 C2 C14 -168.8(3) no . . . . C2 C1 C9 C11 -11.5(5) no . . . . C2 C1 C9 C23 168.2(3) no . . . . C9 C1 C2 C7 -166.3(3) no . . . . C9 C1 C2 C14 11.1(5) no . . . . C8 C1 C9 C11 168.4(3) no . . . . C8 C1 C9 C23 -11.9(5) no . . . . C9 C1 C8 F1 -43.5(4) no . . . . C9 C1 C8 F3 76.2(4) no . . . . C9 C1 C8 F4 -163.0(3) no . . . . C1 C2 C7 C18 177.4(3) no . . . . C1 C2 C14 C12 0.9(5) no . . . . C1 C2 C14 C19 -176.8(3) no . . . . C7 C2 C14 C12 178.5(3) no . . . . C7 C2 C14 C19 0.8(4) no . . . . C14 C2 C7 C18 -0.0(5) no . . . . C2 C7 C18 C15 -177.9(3) no . . . . C2 C7 C18 C25 -0.4(5) no . . . . C1 C9 C11 C12 -0.3(5) no . . . . C1 C9 C11 C24 179.3(3) no . . . . C1 C9 C23 C26 -178.7(3) no . . . . C11 C9 C23 C26 1.0(5) no . . . . C23 C9 C11 C12 -180.0(3) no . . . . C23 C9 C11 C24 -0.4(5) no . . . . C9 C11 C12 C14 12.5(5) no . . . . C9 C11 C12 C20 -168.9(3) no . . . . C9 C11 C24 C28 -0.6(5) no . . . . C12 C11 C24 C28 178.9(3) no . . . . C24 C11 C12 C14 -167.0(3) no . . . . C24 C11 C12 C20 11.6(5) no . . . . C11 C12 C14 C2 -12.8(5) no . . . . C11 C12 C14 C19 164.8(3) no . . . . C11 C12 C20 F2 -83.2(5) no . . . . C11 C12 C20 F7 156.5(4) no . . . . C11 C12 C20 F8 38.4(5) no . . . . C14 C12 C20 F2 95.4(4) no . . . . C14 C12 C20 F7 -24.9(6) no . . . . C14 C12 C20 F8 -143.0(4) no . . . . C20 C12 C14 C2 168.7(3) no . . . . C20 C12 C14 C19 -13.7(5) no . . . . C2 C14 C19 C25 -1.0(5) no . . . . C12 C14 C19 C25 -178.7(3) no . . . . C13 C16 C21 C22 178.7(4) no . . . . C13 C16 C29 C30 -179.2(4) no . . . . C21 C16 C29 C30 0.3(6) no . . . . C29 C16 C21 C22 -0.8(6) no . . . . C7 C18 C25 C19 0.2(5) no . . . . C15 C18 C25 C19 177.7(3) no . . . . C14 C19 C25 C18 0.6(6) no . . . . C16 C21 C22 C27 1.4(6) no . . . . C21 C22 C27 C30 -1.5(7) no . . . . C9 C23 C26 C28 -0.6(6) no . . . . C11 C24 C28 C26 1.1(6) no . . . . C23 C26 C28 C24 -0.5(6) no . . . . C22 C27 C30 C29 0.9(7) no . . . . C16 C29 C30 C27 -0.3(7) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 C2 3.566(4) no . . F1 C9 2.818(5) no . . F1 C23 2.770(5) no . . F2 C11 3.144(5) no . . F2 C14 3.276(4) no . . F2 C19 3.493(4) no . . F2 C24 3.252(5) no . . F3 C2 3.357(4) no . . F3 C9 3.065(4) no . . F3 C23 3.099(4) no . . F4 C2 2.845(4) no . . F4 C7 2.696(5) no . . F7 C14 2.816(4) no . . F7 C19 2.692(4) no . . F8 C11 2.817(4) no . . F8 C14 3.584(4) no . . F8 C24 2.742(5) no . . C1 C12 2.804(5) no . . C2 C11 2.846(4) no . . C2 C25 2.806(5) no . . C7 C8 3.011(5) no . . C7 C13 3.534(5) no . . C7 C19 2.759(5) no . . C8 C23 2.897(5) no . . C9 C14 2.831(5) no . . C9 C28 2.815(5) no . . C11 C26 2.810(6) no . . C13 C25 3.527(5) no . . C14 C18 2.839(4) no . . C15 C21 3.536(5) no . . C15 C29 3.529(5) no . . C16 C27 2.765(5) no . . C19 C20 2.979(5) no . . C20 C24 2.928(6) no . . C21 C30 2.744(5) no . . C22 C29 2.724(5) no . . C23 C24 2.763(6) no . . F1 C26 3.309(4) no . 2_576 F1 C28 3.478(5) no . 2_576 F2 F3 3.182(4) no . 1_556 F2 F3 3.039(3) no . 2_676 F2 F4 3.598(3) no . 1_556 F2 C27 3.519(5) no . 2_766 F3 F2 3.182(4) no . 1_554 F3 F2 3.039(3) no . 2_676 F3 C11 3.458(5) no . 2_676 F3 C12 3.361(5) no . 2_676 F4 F2 3.598(3) no . 1_554 F4 F7 3.597(4) no . 1_554 F4 C19 3.555(4) no . 2_666 F4 C25 3.229(4) no . 2_666 F7 F4 3.597(4) no . 1_556 F7 C29 3.430(5) no . 1_456 F7 C30 3.275(5) no . 1_456 F8 C16 3.577(5) no . 2_666 F8 C21 3.483(5) no . 2_666 C7 C26 3.477(5) no . 2_676 C11 F3 3.458(5) no . 2_676 C11 C21 3.564(5) no . 2_666 C12 F3 3.361(5) no . 2_676 C16 F8 3.577(5) no . 2_666 C18 C26 3.399(5) no . 2_676 C19 F4 3.555(4) no . 2_666 C21 F8 3.483(5) no . 2_666 C21 C11 3.564(5) no . 2_666 C21 C24 3.569(6) no . 2_666 C24 C21 3.569(6) no . 2_666 C25 F4 3.229(4) no . 2_666 C26 F1 3.309(4) no . 2_576 C26 C7 3.477(5) no . 2_676 C26 C18 3.399(5) no . 2_676 C27 F2 3.519(5) no . 2_766 C28 F1 3.478(5) no . 2_576 C29 F7 3.430(5) no . 1_654 C30 F7 3.275(5) no . 1_654 F1 H5 2.3259 no . . F2 H2 3.0373 no . . F2 H6 2.7112 no . . F3 H1 3.1978 no . . F3 H5 2.5532 no . . F4 H1 2.0835 no . . F7 H2 2.1536 no . . F8 H6 2.3037 no . . C1 H1 2.6772 no . . C1 H5 2.7002 no . . C2 H2 3.3028 no . . C7 H7 3.2151 no . . C8 H1 2.6861 no . . C8 H5 2.5930 no . . C9 H6 3.3001 no . . C9 H8 3.2537 no . . C11 H5 3.3010 no . . C11 H10 3.2925 no . . C12 H2 2.7006 no . . C12 H6 2.7118 no . . C13 H1 3.4888 no . . C13 H3 2.5687 no . . C13 H7 3.4829 no . . C13 H11 2.6142 no . . C14 H1 3.2920 no . . C14 H7 3.2588 no . . C15 H1 2.5895 no . . C15 H3 3.4576 no . . C15 H7 2.6169 no . . C15 H11 3.4903 no . . C16 H4 3.2061 no . . C16 H12 3.2271 no . . C18 H2 3.2187 no . . C20 H2 2.6916 no . . C20 H6 2.6298 no . . C21 H9 3.2162 no . . C21 H11 3.2184 no . . C22 H12 3.1986 no . . C23 H10 3.1749 no . . C24 H8 3.2214 no . . C25 H1 3.2132 no . . C26 H6 3.2086 no . . C27 H3 3.2316 no . . C27 H11 3.2110 no . . C28 H5 3.1995 no . . C29 H3 3.2005 no . . C29 H9 3.2150 no . . C30 H4 3.1991 no . . H2 H7 2.2159 no . . H3 H4 2.3122 no . . H4 H9 2.3056 no . . H5 H8 2.2024 no . . H6 H10 2.3114 no . . H8 H10 2.2770 no . . H9 H12 2.3071 no . . H11 H12 2.2898 no . . F1 H4 2.9512 no . 1_465 F1 H7 3.5060 no . 2_666 F1 H8 2.8200 no . 2_576 F1 H10 3.1667 no . 2_576 F2 H4 3.0149 no . 1_466 F2 H9 2.9622 no . 1_466 F2 H9 3.0058 no . 2_766 F3 H4 2.9866 no . 1_465 F3 H9 2.8250 no . 2_765 F4 H2 3.4905 no . 2_666 F4 H7 2.9685 no . 2_666 F4 H9 2.9963 no . 2_765 F4 H12 3.0295 no . 2_765 F7 H11 2.9614 no . 1_456 F7 H12 2.6081 no . 1_456 F8 H4 3.3941 no . 1_466 F8 H10 3.0046 no . 2_577 F8 H11 3.0675 no . 1_456 C8 H4 3.5698 no . 1_465 C8 H9 3.5126 no . 2_765 C9 H3 3.0967 no . 2_666 C11 H3 3.0068 no . 2_666 C13 H7 3.4914 no . 2_766 C15 H8 3.4369 no . 2_676 C15 H10 3.4839 no . 2_676 C16 H7 3.1087 no . 2_766 C18 H8 3.2960 no . 2_676 C21 H5 3.2081 no . 1_645 C21 H7 3.4734 no . 2_766 C21 H8 3.3394 no . 1_645 C22 H2 3.3492 no . 2_766 C22 H5 3.1197 no . 1_645 C22 H6 3.1211 no . 1_644 C23 H3 3.4751 no . 1_465 C23 H3 3.3150 no . 2_666 C23 H4 3.5854 no . 1_465 C24 H3 3.1650 no . 2_666 C24 H9 3.2288 no . 1_466 C25 H8 3.5112 no . 2_676 C26 H3 3.4112 no . 1_465 C26 H3 3.4683 no . 2_666 C27 H2 3.0322 no . 2_766 C27 H6 2.9000 no . 1_644 C28 H1 3.4611 no . 2_676 C28 H3 3.4007 no . 2_666 C28 H4 3.5053 no . 2_666 C29 H2 3.5266 no . 2_766 C29 H7 3.2698 no . 2_766 C29 H11 3.1986 no . 2_765 C30 H1 3.4362 no . 2_765 C30 H2 3.1355 no . 2_766 H1 C28 3.4611 no . 2_676 H1 C30 3.4362 no . 2_765 H1 H9 3.3515 no . 2_765 H1 H10 3.5531 no . 2_676 H1 H12 2.7907 no . 2_765 H2 F4 3.4905 no . 2_666 H2 C22 3.3492 no . 2_766 H2 C27 3.0322 no . 2_766 H2 C29 3.5266 no . 2_766 H2 C30 3.1355 no . 2_766 H2 H9 3.3538 no . 2_766 H2 H12 3.3908 no . 2_766 H3 C9 3.0967 no . 2_666 H3 C11 3.0068 no . 2_666 H3 C23 3.4751 no . 1_645 H3 C23 3.3150 no . 2_666 H3 C24 3.1650 no . 2_666 H3 C26 3.4112 no . 1_645 H3 C26 3.4683 no . 2_666 H3 C28 3.4007 no . 2_666 H3 H5 2.8765 no . 1_645 H3 H8 2.7187 no . 1_645 H4 F1 2.9512 no . 1_645 H4 F2 3.0149 no . 1_644 H4 F3 2.9866 no . 1_645 H4 F8 3.3941 no . 1_644 H4 C8 3.5698 no . 1_645 H4 C23 3.5854 no . 1_645 H4 C28 3.5053 no . 2_666 H4 H5 2.6633 no . 1_645 H4 H6 3.0678 no . 1_644 H4 H10 3.5389 no . 2_666 H5 C21 3.2081 no . 1_465 H5 C22 3.1197 no . 1_465 H5 H3 2.8765 no . 1_465 H5 H4 2.6633 no . 1_465 H5 H8 3.5182 no . 2_576 H6 C22 3.1211 no . 1_466 H6 C27 2.9000 no . 1_466 H6 H4 3.0678 no . 1_466 H6 H9 2.5878 no . 1_466 H7 F1 3.5060 no . 2_666 H7 F4 2.9685 no . 2_666 H7 C13 3.4914 no . 2_766 H7 C16 3.1087 no . 2_766 H7 C21 3.4734 no . 2_766 H7 C29 3.2698 no . 2_766 H7 H11 3.5602 no . 2_766 H8 F1 2.8200 no . 2_576 H8 C15 3.4369 no . 2_676 H8 C18 3.2960 no . 2_676 H8 C21 3.3394 no . 1_465 H8 C25 3.5112 no . 2_676 H8 H3 2.7187 no . 1_465 H8 H5 3.5182 no . 2_576 H9 F2 2.9622 no . 1_644 H9 F2 3.0058 no . 2_766 H9 F3 2.8250 no . 2_765 H9 F4 2.9963 no . 2_765 H9 C8 3.5126 no . 2_765 H9 C24 3.2288 no . 1_644 H9 H1 3.3515 no . 2_765 H9 H2 3.3538 no . 2_766 H9 H6 2.5878 no . 1_644 H10 F1 3.1667 no . 2_576 H10 F8 3.0046 no . 2_577 H10 C15 3.4839 no . 2_676 H10 H1 3.5531 no . 2_676 H10 H4 3.5389 no . 2_666 H10 H11 3.2011 no . 2_676 H11 F7 2.9614 no . 1_654 H11 F8 3.0675 no . 1_654 H11 C29 3.1986 no . 2_765 H11 H7 3.5602 no . 2_766 H11 H10 3.2011 no . 2_676 H11 H11 2.9697 no . 2_765 H12 F4 3.0295 no . 2_765 H12 F7 2.6081 no . 1_654 H12 H1 2.7907 no . 2_765 H12 H2 3.3908 no . 2_766 data_TY_26diPh_BisCF3_Anth _database_code_depnum_ccdc_archive 'CCDC 924505' #TrackingRef '17756_web_deposit_cif_file_1_TakashiYamazaki_1360897912.Comp.3l.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C28 H16 F6' _chemical_formula_moiety 'C28 H16 F6' _chemical_formula_weight 466.42 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 9.7598(16) _cell_length_b 9.8853(16) _cell_length_c 11.7566(19) _cell_angle_alpha 71.537(5) _cell_angle_beta 81.277(6) _cell_angle_gamma 76.796(5) _cell_volume 1043.6(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6773 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 27.60 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476.00 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.988 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku XtaLAB mini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.827 _diffrn_reflns_number 11112 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4778 _reflns_number_gt 2289 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.2548 _refine_ls_number_restraints 456 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4778 _refine_ls_number_parameters 362 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1201P)^2^+0.2914P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.580 _refine_diff_density_min -0.580 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.1223(11) 0.8701(13) 0.3887(9) 0.052(3) Uani 0.401(6) 2 d . . . F1a F 0.0790(9) 0.8770(10) 0.3665(6) 0.077(3) Uani 0.599(6) 2 d . . . F2 F -0.0611(7) 0.7840(9) 0.3952(8) 0.071(3) Uani 0.401(6) 2 d . . . F2a F -0.0843(5) 0.7708(7) 0.4726(7) 0.0850(18) Uani 0.599(6) 2 d . . . F3 F -0.0101(10) 0.8184(11) 0.5527(8) 0.084(3) Uani 0.401(6) 2 d . . . F3a F 0.0656(6) 0.8241(6) 0.5555(5) 0.0615(15) Uani 0.599(6) 2 d . . . F4 F 0.5869(8) 0.2883(9) 0.4617(8) 0.068(2) Uani 0.401(6) 2 d . . . F5 F 0.5173(12) 0.1805(12) 0.6422(8) 0.127(4) Uani 0.401(6) 2 d . . . F6 F 0.4431(9) 0.1450(8) 0.4916(9) 0.102(3) Uani 0.401(6) 2 d . . . F6a F 0.4313(6) 0.1174(5) 0.5978(6) 0.0856(17) Uani 0.599(6) 2 d . . . F5a F 0.5550(6) 0.2483(6) 0.6272(5) 0.0696(15) Uani 0.599(6) 2 d . . . F4a F 0.5708(8) 0.2215(8) 0.4585(6) 0.117(3) Uani 0.599(6) 2 d . . . C1 C 0.1972(4) 0.6687(4) 0.2585(3) 0.0417(9) Uani 1.0 2 d . . . C2 C 0.2690(4) 0.6288(4) 0.1619(4) 0.0440(9) Uani 1.0 2 d . . . C3 C 0.3672(5) 0.4961(5) 0.1847(4) 0.0581(12) Uani 1.0 2 d . . . C4 C 0.3926(5) 0.4118(5) 0.2968(4) 0.0574(11) Uani 1.0 2 d . . . C5 C 0.3239(4) 0.4518(4) 0.4008(4) 0.0433(9) Uani 1.0 2 d . . . C6 C 0.3526(4) 0.3704(4) 0.5192(4) 0.0440(9) Uani 1.0 2 d . . . C7 C 0.2699(4) 0.4046(4) 0.6188(3) 0.0384(8) Uani 1.0 2 d . . . C8 C 0.2923(4) 0.3225(4) 0.7408(4) 0.0434(9) Uani 1.0 2 d . . . C9 C 0.2067(4) 0.3514(4) 0.8364(4) 0.0407(9) Uani 1.0 2 d . . . C10 C 0.0863(4) 0.4635(4) 0.8124(4) 0.0440(9) Uani 1.0 2 d . . . C11 C 0.0627(4) 0.5489(4) 0.6998(4) 0.0442(9) Uani 1.0 2 d . . . C12 C 0.1570(4) 0.5292(4) 0.5977(3) 0.0392(8) Uani 1.0 2 d . . . C13 C 0.1429(4) 0.6235(4) 0.4804(4) 0.0406(9) Uani 1.0 2 d . . . C14 C 0.2187(4) 0.5848(4) 0.3803(3) 0.0397(9) Uani 1.0 2 d . . . C15 C 0.4742(5) 0.2428(5) 0.5396(4) 0.0760(13) Uani 1.0 2 d . . . C16 C 0.0492(5) 0.7722(4) 0.4630(4) 0.0543(10) Uani 1.0 2 d . . . C17 C 0.2460(4) 0.7193(4) 0.0369(3) 0.0419(9) Uani 1.0 2 d . . . C18 C 0.2027(5) 0.8704(4) 0.0074(4) 0.0491(10) Uani 1.0 2 d . . . C19 C 0.1822(5) 0.9520(5) -0.1094(4) 0.0564(11) Uani 1.0 2 d . . . C20 C 0.2073(5) 0.8888(5) -0.2008(4) 0.0564(11) Uani 1.0 2 d . . . C21 C 0.2497(4) 0.7407(5) -0.1741(4) 0.0529(10) Uani 1.0 2 d . . . C22 C 0.2691(4) 0.6575(5) -0.0571(4) 0.0472(10) Uani 1.0 2 d . . . C23 C 0.2392(4) 0.2685(4) 0.9617(3) 0.0400(9) Uani 1.0 2 d . . . C24 C 0.3781(5) 0.2150(5) 0.9911(4) 0.0527(10) Uani 1.0 2 d . . . C25 C 0.4071(5) 0.1380(5) 1.1072(4) 0.0614(12) Uani 1.0 2 d . . . C26 C 0.3005(5) 0.1133(5) 1.1969(4) 0.0562(11) Uani 1.0 2 d . . . C27 C 0.1627(5) 0.1644(4) 1.1699(4) 0.0510(10) Uani 1.0 2 d . . . C28 C 0.1323(4) 0.2417(4) 1.0531(4) 0.0442(9) Uani 1.0 2 d . . . H1 H 0.1308 0.7550 0.2446 0.0501 Uiso 1.0 2 calc R . . H3 H 0.4160 0.4661 0.1198 0.0697 Uiso 1.0 2 calc R . . H4 H 0.4571 0.3244 0.3071 0.0689 Uiso 1.0 2 calc R . . H8 H 0.3691 0.2456 0.7557 0.0521 Uiso 1.0 2 calc R . . H10 H 0.0216 0.4788 0.8761 0.0528 Uiso 1.0 2 calc R . . H11 H -0.0169 0.6227 0.6879 0.0530 Uiso 1.0 2 calc R . . H18 H 0.1877 0.9159 0.0675 0.0589 Uiso 1.0 2 calc R . . H19 H 0.1508 1.0519 -0.1268 0.0677 Uiso 1.0 2 calc R . . H20 H 0.1956 0.9456 -0.2799 0.0677 Uiso 1.0 2 calc R . . H21 H 0.2655 0.6965 -0.2351 0.0634 Uiso 1.0 2 calc R . . H22 H 0.2984 0.5573 -0.0405 0.0566 Uiso 1.0 2 calc R . . H24 H 0.4520 0.2316 0.9316 0.0632 Uiso 1.0 2 calc R . . H25 H 0.5004 0.1021 1.1252 0.0737 Uiso 1.0 2 calc R . . H26 H 0.3213 0.0622 1.2755 0.0674 Uiso 1.0 2 calc R . . H27 H 0.0897 0.1470 1.2302 0.0612 Uiso 1.0 2 calc R . . H28 H 0.0386 0.2762 1.0356 0.0530 Uiso 1.0 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.067(5) 0.029(4) 0.053(5) -0.001(4) -0.012(4) -0.004(3) F1a 0.111(6) 0.041(3) 0.051(3) 0.016(4) 0.000(4) -0.001(3) F2 0.042(4) 0.058(4) 0.090(5) 0.014(3) -0.011(4) -0.004(4) F2a 0.049(3) 0.069(3) 0.124(5) 0.013(3) -0.013(3) -0.025(4) F3 0.091(6) 0.062(4) 0.064(4) 0.031(5) 0.014(4) -0.013(3) F3a 0.084(4) 0.042(3) 0.052(3) 0.010(3) -0.003(3) -0.0216(18) F4 0.045(4) 0.070(5) 0.081(4) 0.023(4) -0.008(3) -0.035(4) F5 0.122(6) 0.097(6) 0.103(5) 0.053(5) -0.012(5) 0.004(5) F6 0.105(5) 0.040(4) 0.137(6) 0.013(4) 0.022(5) -0.029(4) F6a 0.092(4) 0.032(3) 0.126(5) 0.008(2) -0.039(3) -0.015(3) F5a 0.051(3) 0.059(4) 0.085(3) -0.005(3) -0.015(3) -0.002(3) F4a 0.098(4) 0.101(5) 0.105(4) 0.055(4) 0.013(4) -0.025(4) C1 0.043(2) 0.038(2) 0.040(2) -0.0010(16) -0.0040(16) -0.0103(16) C2 0.045(2) 0.044(2) 0.043(2) -0.0057(16) -0.0031(17) -0.0147(16) C3 0.066(3) 0.055(3) 0.043(3) 0.014(2) -0.0011(19) -0.0196(18) C4 0.062(3) 0.052(3) 0.048(3) 0.010(2) -0.0004(19) -0.0178(19) C5 0.045(2) 0.038(2) 0.042(2) -0.0013(16) -0.0008(16) -0.0106(16) C6 0.0414(19) 0.0344(19) 0.047(2) 0.0010(15) 0.0029(16) -0.0079(16) C7 0.0389(19) 0.0326(18) 0.0396(19) -0.0032(14) -0.0016(15) -0.0082(15) C8 0.044(2) 0.0336(19) 0.046(2) -0.0006(16) -0.0022(17) -0.0080(16) C9 0.042(2) 0.0369(19) 0.041(2) -0.0079(15) -0.0029(16) -0.0088(15) C10 0.044(2) 0.044(2) 0.041(2) -0.0064(16) 0.0042(16) -0.0133(16) C11 0.044(2) 0.038(2) 0.044(2) -0.0011(16) 0.0002(17) -0.0095(16) C12 0.0394(19) 0.0370(19) 0.0393(19) -0.0052(15) -0.0003(15) -0.0115(15) C13 0.0392(19) 0.0357(19) 0.043(2) -0.0019(15) -0.0018(16) -0.0105(15) C14 0.042(2) 0.0348(19) 0.0396(19) -0.0052(15) -0.0016(16) -0.0099(15) C15 0.081(3) 0.059(3) 0.063(3) 0.023(3) 0.001(3) -0.012(2) C16 0.062(3) 0.042(2) 0.049(3) 0.0043(18) 0.0021(19) -0.0121(17) C17 0.040(2) 0.045(2) 0.0387(19) -0.0065(16) -0.0001(16) -0.0135(16) C18 0.058(3) 0.046(3) 0.044(3) -0.0099(18) -0.0023(18) -0.0163(17) C19 0.067(3) 0.048(3) 0.050(3) -0.009(2) -0.007(2) -0.0095(18) C20 0.058(3) 0.067(3) 0.039(3) -0.016(2) -0.0072(19) -0.0032(19) C21 0.054(3) 0.067(3) 0.041(3) -0.013(2) -0.0020(19) -0.0205(19) C22 0.049(3) 0.049(3) 0.044(2) -0.0077(17) -0.0018(17) -0.0156(17) C23 0.046(2) 0.0340(19) 0.0404(19) -0.0084(15) -0.0060(16) -0.0105(15) C24 0.046(3) 0.060(3) 0.049(3) -0.0099(19) -0.0054(18) -0.0106(19) C25 0.052(3) 0.066(3) 0.058(3) -0.003(2) -0.015(2) -0.007(2) C26 0.068(3) 0.054(3) 0.039(3) -0.003(2) -0.0126(19) -0.0048(18) C27 0.060(3) 0.048(3) 0.039(2) -0.0096(19) 0.0017(18) -0.0080(17) C28 0.046(2) 0.040(2) 0.042(2) -0.0041(16) -0.0023(17) -0.0099(16) #============================================================================== _computing_data_collection 'CrystalClear-SM Auto 2.0 r1 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Auto 2.0 r1' _computing_data_reduction 'CrystalClear-SM Auto 2.0 r1' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C16 1.341(12) yes . . F1a C16 1.318(8) yes . . F2 C16 1.396(10) yes . . F2a C16 1.294(7) yes . . F3 C16 1.287(11) yes . . F3a C16 1.384(8) yes . . F4 C15 1.382(9) yes . . F5 C15 1.255(10) yes . . F6 C15 1.371(12) yes . . F6a C15 1.340(7) yes . . F5a C15 1.409(8) yes . . F4a C15 1.268(9) yes . . C1 C2 1.362(6) yes . . C1 C14 1.428(5) yes . . C2 C3 1.412(5) yes . . C2 C17 1.479(5) yes . . C3 C4 1.343(6) yes . . C4 C5 1.428(6) yes . . C5 C6 1.403(5) yes . . C5 C14 1.449(5) yes . . C6 C7 1.405(6) yes . . C6 C15 1.506(6) yes . . C7 C8 1.429(5) yes . . C7 C12 1.436(5) yes . . C8 C9 1.361(6) yes . . C9 C10 1.413(5) yes . . C9 C23 1.484(5) yes . . C10 C11 1.347(5) yes . . C11 C12 1.434(5) yes . . C12 C13 1.405(5) yes . . C13 C14 1.404(6) yes . . C13 C16 1.514(5) yes . . C17 C18 1.399(6) yes . . C17 C22 1.390(7) yes . . C18 C19 1.372(6) yes . . C19 C20 1.372(7) yes . . C20 C21 1.373(7) yes . . C21 C22 1.377(5) yes . . C23 C24 1.391(6) yes . . C23 C28 1.385(5) yes . . C24 C25 1.372(6) yes . . C25 C26 1.369(6) yes . . C26 C27 1.372(6) yes . . C27 C28 1.383(5) yes . . C1 H1 0.930 no . . C3 H3 0.930 no . . C4 H4 0.930 no . . C8 H8 0.930 no . . C10 H10 0.930 no . . C11 H11 0.930 no . . C18 H18 0.930 no . . C19 H19 0.930 no . . C20 H20 0.930 no . . C21 H21 0.930 no . . C22 H22 0.930 no . . C24 H24 0.930 no . . C25 H25 0.930 no . . C26 H26 0.930 no . . C27 H27 0.930 no . . C28 H28 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C14 123.3(3) yes . . . C1 C2 C3 117.6(4) yes . . . C1 C2 C17 122.0(3) yes . . . C3 C2 C17 120.4(4) yes . . . C2 C3 C4 122.2(4) yes . . . C3 C4 C5 122.2(4) yes . . . C4 C5 C6 123.9(4) yes . . . C4 C5 C14 116.8(3) yes . . . C6 C5 C14 119.3(4) yes . . . C5 C6 C7 121.5(3) yes . . . C5 C6 C15 119.0(4) yes . . . C7 C6 C15 119.4(4) yes . . . C6 C7 C8 123.6(3) yes . . . C6 C7 C12 118.7(3) yes . . . C8 C7 C12 117.8(4) yes . . . C7 C8 C9 123.1(3) yes . . . C8 C9 C10 117.9(4) yes . . . C8 C9 C23 121.1(3) yes . . . C10 C9 C23 121.1(4) yes . . . C9 C10 C11 121.7(4) yes . . . C10 C11 C12 121.8(3) yes . . . C7 C12 C11 117.0(3) yes . . . C7 C12 C13 119.5(3) yes . . . C11 C12 C13 123.5(3) yes . . . C12 C13 C14 121.2(3) yes . . . C12 C13 C16 119.0(4) yes . . . C14 C13 C16 119.7(3) yes . . . C1 C14 C5 117.8(4) yes . . . C1 C14 C13 123.7(3) yes . . . C5 C14 C13 118.5(3) yes . . . F4 C15 F5 108.0(7) yes . . . F4 C15 F6 101.5(7) yes . . . F4 C15 C6 106.8(5) yes . . . F5 C15 F6 110.9(8) yes . . . F5 C15 C6 121.3(6) yes . . . F6 C15 C6 106.6(5) yes . . . F6a C15 F5a 99.1(5) yes . . . F6a C15 F4a 108.7(6) yes . . . F6a C15 C6 112.0(4) yes . . . F5a C15 F4a 100.7(6) yes . . . F5a C15 C6 109.5(5) yes . . . F4a C15 C6 123.6(5) yes . . . F1 C16 F2 102.3(6) yes . . . F1 C16 F3 108.9(8) yes . . . F1 C16 C13 107.7(6) yes . . . F1a C16 F2a 109.2(6) yes . . . F1a C16 F3a 102.4(6) yes . . . F1a C16 C13 117.6(5) yes . . . F2 C16 F3 105.2(7) yes . . . F2 C16 C13 109.3(5) yes . . . F2a C16 F3a 104.4(5) yes . . . F2a C16 C13 113.8(5) yes . . . F3 C16 C13 121.8(5) yes . . . F3a C16 C13 108.1(4) yes . . . C2 C17 C18 121.8(4) yes . . . C2 C17 C22 121.1(4) yes . . . C18 C17 C22 117.1(4) yes . . . C17 C18 C19 120.7(5) yes . . . C18 C19 C20 121.2(4) yes . . . C19 C20 C21 119.1(4) yes . . . C20 C21 C22 120.2(5) yes . . . C17 C22 C21 121.7(4) yes . . . C9 C23 C24 121.0(3) yes . . . C9 C23 C28 121.1(4) yes . . . C24 C23 C28 117.9(4) yes . . . C23 C24 C25 120.6(4) yes . . . C24 C25 C26 121.0(4) yes . . . C25 C26 C27 119.5(4) yes . . . C26 C27 C28 120.0(4) yes . . . C23 C28 C27 121.0(4) yes . . . C2 C1 H1 118.338 no . . . C14 C1 H1 118.352 no . . . C2 C3 H3 118.883 no . . . C4 C3 H3 118.881 no . . . C3 C4 H4 118.916 no . . . C5 C4 H4 118.922 no . . . C7 C8 H8 118.434 no . . . C9 C8 H8 118.431 no . . . C9 C10 H10 119.169 no . . . C11 C10 H10 119.161 no . . . C10 C11 H11 119.080 no . . . C12 C11 H11 119.072 no . . . C17 C18 H18 119.646 no . . . C19 C18 H18 119.650 no . . . C18 C19 H19 119.407 no . . . C20 C19 H19 119.404 no . . . C19 C20 H20 120.436 no . . . C21 C20 H20 120.450 no . . . C20 C21 H21 119.894 no . . . C22 C21 H21 119.902 no . . . C17 C22 H22 119.156 no . . . C21 C22 H22 119.158 no . . . C23 C24 H24 119.708 no . . . C25 C24 H24 119.713 no . . . C24 C25 H25 119.525 no . . . C26 C25 H25 119.523 no . . . C25 C26 H26 120.243 no . . . C27 C26 H26 120.251 no . . . C26 C27 H27 119.995 no . . . C28 C27 H27 119.994 no . . . C23 C28 H28 119.476 no . . . C27 C28 H28 119.485 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C14 C5 0.9(6) no . . . . C2 C1 C14 C13 -178.5(4) no . . . . C14 C1 C2 C3 1.3(7) no . . . . C14 C1 C2 C17 -179.0(4) no . . . . C1 C2 C3 C4 -1.2(7) no . . . . C1 C2 C17 C18 28.7(6) no . . . . C1 C2 C17 C22 -152.5(4) no . . . . C3 C2 C17 C18 -151.6(4) no . . . . C3 C2 C17 C22 27.2(6) no . . . . C17 C2 C3 C4 179.1(4) no . . . . C2 C3 C4 C5 -1.2(8) no . . . . C3 C4 C5 C6 -176.7(5) no . . . . C3 C4 C5 C14 3.4(7) no . . . . C4 C5 C6 C7 -171.9(4) no . . . . C4 C5 C6 C15 7.6(7) no . . . . C4 C5 C14 C1 -3.1(6) no . . . . C4 C5 C14 C13 176.3(4) no . . . . C6 C5 C14 C1 176.9(4) no . . . . C6 C5 C14 C13 -3.6(6) no . . . . C14 C5 C6 C7 8.1(6) no . . . . C14 C5 C6 C15 -172.4(4) no . . . . C5 C6 C7 C8 178.1(4) no . . . . C5 C6 C7 C12 -2.3(6) no . . . . C5 C6 C15 F4 45.0(6) no . . . . C5 C6 C15 F5 169.1(4) no . . . . C5 C6 C15 F6 -62.9(5) no . . . . C5 C6 C15 F6a -117.7(5) no . . . . C5 C6 C15 F5a 133.4(4) no . . . . C5 C6 C15 F4a 15.4(8) no . . . . C7 C6 C15 F4 -135.5(4) no . . . . C7 C6 C15 F5 -11.4(7) no . . . . C7 C6 C15 F6 116.6(4) no . . . . C7 C6 C15 F6a 61.8(6) no . . . . C7 C6 C15 F5a -47.1(6) no . . . . C7 C6 C15 F4a -165.1(5) no . . . . C15 C6 C7 C8 -1.4(7) no . . . . C15 C6 C7 C12 178.2(4) no . . . . C6 C7 C8 C9 -176.1(4) no . . . . C6 C7 C12 C11 171.5(4) no . . . . C6 C7 C12 C13 -7.9(6) no . . . . C8 C7 C12 C11 -8.9(6) no . . . . C8 C7 C12 C13 171.7(4) no . . . . C12 C7 C8 C9 4.3(6) no . . . . C7 C8 C9 C10 3.3(7) no . . . . C7 C8 C9 C23 -176.4(4) no . . . . C8 C9 C10 C11 -6.1(7) no . . . . C8 C9 C23 C24 31.9(6) no . . . . C8 C9 C23 C28 -148.0(4) no . . . . C10 C9 C23 C24 -147.7(4) no . . . . C10 C9 C23 C28 32.4(6) no . . . . C23 C9 C10 C11 173.5(4) no . . . . C9 C10 C11 C12 1.2(7) no . . . . C10 C11 C12 C7 6.5(7) no . . . . C10 C11 C12 C13 -174.2(4) no . . . . C7 C12 C13 C14 12.4(6) no . . . . C7 C12 C13 C16 -164.7(4) no . . . . C11 C12 C13 C14 -166.8(4) no . . . . C11 C12 C13 C16 16.1(6) no . . . . C12 C13 C14 C1 172.8(4) no . . . . C12 C13 C14 C5 -6.6(6) no . . . . C12 C13 C16 F1 131.5(4) no . . . . C12 C13 C16 F1a 153.0(4) no . . . . C12 C13 C16 F2 -118.1(4) no . . . . C12 C13 C16 F2a -77.6(5) no . . . . C12 C13 C16 F3 4.8(7) no . . . . C12 C13 C16 F3a 37.9(5) no . . . . C14 C13 C16 F1 -45.6(6) no . . . . C14 C13 C16 F1a -24.1(6) no . . . . C14 C13 C16 F2 64.7(5) no . . . . C14 C13 C16 F2a 105.3(4) no . . . . C14 C13 C16 F3 -172.4(4) no . . . . C14 C13 C16 F3a -139.3(4) no . . . . C16 C13 C14 C1 -10.1(6) no . . . . C16 C13 C14 C5 170.5(4) no . . . . C2 C17 C18 C19 179.9(4) no . . . . C2 C17 C22 C21 -179.2(4) no . . . . C18 C17 C22 C21 -0.3(6) no . . . . C22 C17 C18 C19 1.1(6) no . . . . C17 C18 C19 C20 -1.9(7) no . . . . C18 C19 C20 C21 1.9(7) no . . . . C19 C20 C21 C22 -1.1(7) no . . . . C20 C21 C22 C17 0.3(6) no . . . . C9 C23 C24 C25 -179.8(4) no . . . . C9 C23 C28 C27 -180.0(4) no . . . . C24 C23 C28 C27 0.1(6) no . . . . C28 C23 C24 C25 0.1(7) no . . . . C23 C24 C25 C26 -0.7(8) no . . . . C24 C25 C26 C27 1.0(8) no . . . . C25 C26 C27 C28 -0.7(7) no . . . . C26 C27 C28 C23 0.2(7) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 C1 2.787(14) no . . F1 C12 3.464(11) no . . F1 C14 2.790(13) no . . F1a C1 2.703(10) no . . F1a C14 2.863(10) no . . F2 C1 2.975(8) no . . F2 C12 3.439(8) no . . F2 C14 2.996(8) no . . F2a C11 3.165(7) no . . F2a C12 3.110(6) no . . F2a C14 3.333(7) no . . F3 C11 2.680(9) no . . F3 C12 2.879(10) no . . F3a C11 2.716(6) no . . F3a C12 2.752(7) no . . F3a C14 3.551(7) no . . F4 C4 2.721(9) no . . F4 C5 2.765(8) no . . F4 C7 3.507(9) no . . F5 C7 2.862(11) no . . F5 C8 2.644(11) no . . F6 C4 2.892(8) no . . F6 C5 2.899(8) no . . F6 C7 3.371(10) no . . F6a C5 3.420(6) no . . F6a C7 2.981(6) no . . F6a C8 2.999(7) no . . F5a C5 3.545(6) no . . F5a C7 2.857(6) no . . F5a C8 2.760(6) no . . F4a C4 2.723(8) no . . F4a C5 2.909(8) no . . C1 C4 2.760(5) no . . C1 C16 2.956(6) no . . C1 C18 2.995(5) no . . C2 C5 2.856(5) no . . C3 C14 2.801(6) no . . C3 C22 2.966(6) no . . C4 C15 2.938(6) no . . C5 C12 2.828(6) no . . C6 C13 2.807(5) no . . C7 C10 2.803(5) no . . C7 C14 2.853(5) no . . C8 C11 2.760(5) no . . C8 C15 2.939(6) no . . C8 C24 2.975(6) no . . C9 C12 2.846(5) no . . C10 C28 3.004(5) no . . C11 C16 2.955(5) no . . C17 C20 2.797(5) no . . C18 C21 2.751(7) no . . C19 C22 2.733(6) no . . C23 C26 2.784(5) no . . C24 C27 2.750(6) no . . C25 C28 2.738(6) no . . F1 F3 3.275(17) no . 2_576 F1 C26 3.343(12) no . 1_564 F1 C27 3.272(11) no . 1_564 F1a F3a 3.314(11) no . 2_576 F1a C20 3.577(9) no . 2_575 F1a C26 3.486(10) no . 1_564 F1a C27 3.226(9) no . 1_564 F2 C6 3.403(9) no . 2_566 F2 C7 3.113(10) no . 2_566 F2 C8 3.465(11) no . 2_566 F2 C12 3.406(11) no . 2_566 F2 C20 3.452(8) no . 2_575 F2a C5 3.427(7) no . 2_566 F2a C6 3.213(8) no . 2_566 F2a C7 3.262(9) no . 2_566 F2a C12 3.559(9) no . 2_566 F3 F1 3.275(17) no . 2_576 F3 F3 3.450(14) no . 2_576 F3 C27 3.412(10) no . 2_567 F3a F1a 3.314(11) no . 2_576 F3a F3a 3.321(7) no . 2_576 F4 C7 3.433(10) no . 2_666 F4 C12 3.275(10) no . 2_666 F4 C13 3.186(11) no . 2_666 F4 C14 3.501(11) no . 2_666 F4 C21 3.582(10) no . 2_665 F5 C25 3.586(9) no . 2_657 F5 C26 3.218(10) no . 2_657 F6 F6 2.783(10) no . 2_656 F6a C20 3.576(7) no . 1_546 F5a C1 3.305(8) no . 2_666 F5a C5 3.340(8) no . 2_666 F5a C13 3.386(7) no . 2_666 F5a C14 3.021(8) no . 2_666 F5a C26 3.598(6) no . 2_657 F4a C21 3.481(8) no . 2_665 C1 F5a 3.305(8) no . 2_666 C1 C11 3.571(6) no . 2_566 C5 F2a 3.427(7) no . 2_566 C5 F5a 3.340(8) no . 2_666 C6 F2 3.403(9) no . 2_566 C6 F2a 3.213(8) no . 2_566 C7 F2 3.113(10) no . 2_566 C7 F2a 3.262(9) no . 2_566 C7 F4 3.433(10) no . 2_666 C8 F2 3.465(11) no . 2_566 C10 C21 3.525(7) no . 1_556 C11 C1 3.571(6) no . 2_566 C12 F2 3.406(11) no . 2_566 C12 F2a 3.559(9) no . 2_566 C12 F4 3.275(10) no . 2_666 C13 F4 3.186(11) no . 2_666 C13 F5a 3.386(7) no . 2_666 C14 F4 3.501(11) no . 2_666 C14 F5a 3.021(8) no . 2_666 C20 F1a 3.577(9) no . 2_575 C20 F2 3.452(8) no . 2_575 C20 F6a 3.576(7) no . 1_564 C21 F4 3.582(10) no . 2_665 C21 F4a 3.481(8) no . 2_665 C21 C10 3.525(7) no . 1_554 C25 F5 3.586(9) no . 2_657 C26 F1 3.343(12) no . 1_546 C26 F1a 3.486(10) no . 1_546 C26 F5 3.218(10) no . 2_657 C26 F5a 3.598(6) no . 2_657 C27 F1 3.272(11) no . 1_546 C27 F1a 3.226(9) no . 1_546 C27 F3 3.412(10) no . 2_567 F1 H1 2.3045 no . . F1a H1 2.0887 no . . F1a H18 3.4391 no . . F2 H1 2.4076 no . . F2 H11 3.3507 no . . F2a H1 3.1668 no . . F2a H11 2.5885 no . . F3 H11 2.0857 no . . F3a H11 2.3293 no . . F4 H4 2.2628 no . . F5 H8 1.9550 no . . F5 H24 3.5386 no . . F6 H4 2.3354 no . . F6 H8 3.4781 no . . F6a H4 3.3879 no . . F6a H8 2.4936 no . . F5a H8 2.1770 no . . F5a H24 3.5291 no . . F4a H4 2.0905 no . . C1 H3 3.2082 no . . C1 H18 2.7399 no . . C2 H4 3.2421 no . . C2 H18 2.6757 no . . C2 H22 2.6469 no . . C3 H1 3.2124 no . . C3 H22 2.6765 no . . C5 H1 3.3004 no . . C5 H3 3.2566 no . . C6 H4 2.6839 no . . C6 H8 2.6733 no . . C7 H11 3.2869 no . . C8 H10 3.2108 no . . C8 H24 2.7219 no . . C9 H11 3.2430 no . . C9 H24 2.6578 no . . C9 H28 2.6493 no . . C10 H8 3.2155 no . . C10 H28 2.7343 no . . C12 H8 3.2877 no . . C12 H10 3.2652 no . . C13 H1 2.6712 no . . C13 H11 2.6877 no . . C14 H4 3.2925 no . . C15 H4 2.6141 no . . C15 H8 2.5974 no . . C16 H1 2.6175 no . . C16 H11 2.6527 no . . C17 H1 2.6238 no . . C17 H3 2.6488 no . . C17 H19 3.2432 no . . C17 H21 3.2501 no . . C18 H1 2.7071 no . . C18 H20 3.2285 no . . C18 H22 3.2227 no . . C19 H21 3.2078 no . . C20 H18 3.2237 no . . C20 H22 3.2167 no . . C21 H19 3.2047 no . . C22 H3 2.6711 no . . C22 H18 3.2242 no . . C22 H20 3.2250 no . . C23 H8 2.6097 no . . C23 H10 2.6745 no . . C23 H25 3.2354 no . . C23 H27 3.2460 no . . C24 H8 2.7007 no . . C24 H26 3.2227 no . . C24 H28 3.2214 no . . C25 H27 3.2079 no . . C26 H24 3.2190 no . . C26 H28 3.2212 no . . C27 H25 3.2054 no . . C28 H10 2.7256 no . . C28 H24 3.2220 no . . C28 H26 3.2274 no . . H1 H18 2.2647 no . . H3 H4 2.2418 no . . H3 H22 2.1888 no . . H8 H24 2.2859 no . . H10 H11 2.2523 no . . H10 H28 2.2629 no . . H18 H19 2.2888 no . . H19 H20 2.3000 no . . H20 H21 2.3077 no . . H21 H22 2.2934 no . . H24 H25 2.2913 no . . H25 H26 2.2954 no . . H26 H27 2.3053 no . . H27 H28 2.3059 no . . F1 H20 3.4245 no . 2_575 F1 H26 2.9068 no . 1_564 F1 H27 2.7600 no . 1_564 F1a H20 2.9740 no . 2_575 F1a H26 3.1719 no . 1_564 F1a H27 2.6593 no . 1_564 F2 H19 3.2104 no . 2_575 F2 H20 2.7111 no . 2_575 F2a H20 3.0831 no . 2_575 F3 H26 3.5653 no . 2_567 F3 H27 2.6574 no . 2_567 F3a H20 3.1160 no . 1_556 F3a H21 3.1342 no . 1_556 F3a H27 2.7978 no . 2_567 F4 H21 2.8063 no . 2_665 F5 H25 3.2483 no . 2_657 F5 H26 2.5372 no . 2_657 F6 H26 3.3493 no . 1_554 F6a H20 3.0781 no . 1_546 F6a H25 3.3582 no . 2_657 F6a H26 2.9425 no . 2_657 F5a H26 2.9478 no . 2_657 F4a H20 3.3692 no . 2_665 F4a H21 2.8421 no . 2_665 F4a H26 3.5848 no . 2_657 C1 H11 3.5529 no . 2_566 C2 H10 3.3819 no . 2_566 C2 H24 3.2216 no . 2_666 C3 H22 3.4508 no . 2_665 C3 H24 3.3669 no . 2_666 C4 H21 3.3068 no . 2_665 C8 H19 3.1437 no . 1_546 C9 H19 3.0173 no . 1_546 C9 H21 3.4062 no . 1_556 C9 H22 3.1830 no . 1_556 C10 H21 3.0661 no . 1_556 C10 H22 3.3336 no . 1_556 C10 H28 3.4808 no . 2_567 C11 H21 3.0189 no . 1_556 C11 H27 3.3282 no . 2_567 C12 H21 3.3485 no . 1_556 C14 H11 3.4777 no . 2_566 C15 H26 3.4949 no . 2_657 C16 H20 3.5826 no . 2_575 C17 H10 3.4582 no . 2_566 C17 H24 3.1881 no . 2_666 C17 H25 3.3627 no . 2_666 C17 H28 3.0132 no . 2_566 C18 H19 3.5309 no . 2_575 C18 H24 3.4077 no . 2_666 C18 H25 3.1012 no . 2_666 C18 H28 3.2069 no . 2_566 C19 H8 3.5906 no . 1_564 C19 H18 3.5635 no . 2_575 C19 H25 3.0073 no . 2_666 C19 H28 3.3013 no . 2_566 C20 H25 3.1420 no . 2_666 C20 H27 3.0814 no . 2_566 C20 H28 3.2495 no . 2_566 C21 H3 3.4619 no . 2_665 C21 H4 3.0802 no . 2_665 C21 H25 3.3778 no . 2_666 C21 H27 3.3407 no . 2_566 C21 H28 3.0412 no . 2_566 C22 H3 3.1062 no . 2_665 C22 H10 3.5344 no . 2_566 C22 H25 3.4699 no . 2_666 C22 H28 2.9132 no . 2_566 C23 H18 3.4362 no . 1_546 C23 H19 2.9893 no . 1_546 C23 H22 3.0315 no . 1_556 C24 H3 3.3997 no . 1_556 C24 H22 3.2070 no . 1_556 C25 H3 3.3149 no . 1_556 C25 H4 3.5577 no . 1_556 C25 H18 3.5659 no . 1_546 C26 H4 3.4846 no . 1_556 C26 H18 3.2703 no . 1_546 C27 H10 3.4871 no . 2_567 C27 H11 3.0639 no . 2_567 C27 H18 3.0082 no . 1_546 C28 H10 3.1257 no . 2_567 C28 H18 3.0943 no . 1_546 C28 H19 3.2036 no . 1_546 H1 H19 3.1928 no . 2_575 H3 C21 3.4619 no . 2_665 H3 C22 3.1062 no . 2_665 H3 C24 3.3997 no . 1_554 H3 C25 3.3149 no . 1_554 H3 H3 2.9964 no . 2_665 H3 H21 3.4203 no . 2_665 H3 H22 2.7833 no . 2_665 H3 H24 3.3668 no . 2_666 H3 H25 3.4854 no . 1_554 H4 C21 3.0802 no . 2_665 H4 C25 3.5577 no . 1_554 H4 C26 3.4846 no . 1_554 H4 H21 2.6930 no . 2_665 H4 H25 3.4434 no . 1_554 H4 H26 3.3079 no . 1_554 H8 C19 3.5906 no . 1_546 H8 H19 3.0676 no . 1_546 H8 H25 3.3000 no . 2_657 H10 C2 3.3819 no . 2_566 H10 C17 3.4582 no . 2_566 H10 C22 3.5344 no . 2_566 H10 C27 3.4871 no . 2_567 H10 C28 3.1257 no . 2_567 H10 H10 3.0280 no . 2_567 H10 H21 3.4083 no . 1_556 H10 H22 3.3324 no . 1_556 H10 H22 3.4435 no . 2_566 H10 H27 3.4743 no . 2_567 H10 H28 2.8372 no . 2_567 H11 C1 3.5529 no . 2_566 H11 C14 3.4777 no . 2_566 H11 C27 3.0639 no . 2_567 H11 H21 3.3220 no . 1_556 H11 H27 2.6559 no . 2_567 H18 C19 3.5635 no . 2_575 H18 C23 3.4362 no . 1_564 H18 C25 3.5659 no . 1_564 H18 C26 3.2703 no . 1_564 H18 C27 3.0082 no . 1_564 H18 C28 3.0943 no . 1_564 H18 H19 3.2347 no . 2_575 H18 H24 3.4858 no . 2_666 H18 H25 3.5134 no . 2_666 H18 H27 3.3176 no . 1_564 H18 H28 3.4484 no . 1_564 H19 F2 3.2104 no . 2_575 H19 C8 3.1437 no . 1_564 H19 C9 3.0173 no . 1_564 H19 C18 3.5309 no . 2_575 H19 C23 2.9893 no . 1_564 H19 C28 3.2036 no . 1_564 H19 H1 3.1928 no . 2_575 H19 H8 3.0676 no . 1_564 H19 H18 3.2347 no . 2_575 H19 H25 3.3971 no . 2_666 H19 H28 3.2701 no . 1_564 H20 F1 3.4245 no . 2_575 H20 F1a 2.9740 no . 2_575 H20 F2 2.7111 no . 2_575 H20 F2a 3.0831 no . 2_575 H20 F3a 3.1160 no . 1_554 H20 F6a 3.0781 no . 1_564 H20 F4a 3.3692 no . 2_665 H20 C16 3.5826 no . 2_575 H20 H25 3.5753 no . 2_666 H20 H27 3.0442 no . 2_566 H21 F3a 3.1342 no . 1_554 H21 F4 2.8063 no . 2_665 H21 F4a 2.8421 no . 2_665 H21 C4 3.3068 no . 2_665 H21 C9 3.4062 no . 1_554 H21 C10 3.0661 no . 1_554 H21 C11 3.0189 no . 1_554 H21 C12 3.3485 no . 1_554 H21 H3 3.4203 no . 2_665 H21 H4 2.6930 no . 2_665 H21 H10 3.4083 no . 1_554 H21 H11 3.3220 no . 1_554 H21 H27 3.4577 no . 2_566 H21 H28 3.5078 no . 2_566 H22 C3 3.4508 no . 2_665 H22 C9 3.1830 no . 1_554 H22 C10 3.3336 no . 1_554 H22 C23 3.0315 no . 1_554 H22 C24 3.2070 no . 1_554 H22 H3 2.7833 no . 2_665 H22 H10 3.3324 no . 1_554 H22 H10 3.4435 no . 2_566 H22 H24 3.3228 no . 1_554 H22 H28 3.3252 no . 2_566 H24 C2 3.2216 no . 2_666 H24 C3 3.3669 no . 2_666 H24 C17 3.1881 no . 2_666 H24 C18 3.4077 no . 2_666 H24 H3 3.3668 no . 2_666 H24 H18 3.4858 no . 2_666 H24 H22 3.3228 no . 1_556 H24 H25 3.4846 no . 2_657 H25 F5 3.2483 no . 2_657 H25 F6a 3.3582 no . 2_657 H25 C17 3.3627 no . 2_666 H25 C18 3.1012 no . 2_666 H25 C19 3.0073 no . 2_666 H25 C20 3.1420 no . 2_666 H25 C21 3.3778 no . 2_666 H25 C22 3.4699 no . 2_666 H25 H3 3.4854 no . 1_556 H25 H4 3.4434 no . 1_556 H25 H8 3.3000 no . 2_657 H25 H18 3.5134 no . 2_666 H25 H19 3.3971 no . 2_666 H25 H20 3.5753 no . 2_666 H25 H24 3.4846 no . 2_657 H26 F1 2.9068 no . 1_546 H26 F1a 3.1719 no . 1_546 H26 F3 3.5653 no . 2_567 H26 F5 2.5372 no . 2_657 H26 F6 3.3493 no . 1_556 H26 F6a 2.9425 no . 2_657 H26 F5a 2.9478 no . 2_657 H26 F4a 3.5848 no . 2_657 H26 C15 3.4949 no . 2_657 H26 H4 3.3079 no . 1_556 H27 F1 2.7600 no . 1_546 H27 F1a 2.6593 no . 1_546 H27 F3 2.6574 no . 2_567 H27 F3a 2.7978 no . 2_567 H27 C11 3.3282 no . 2_567 H27 C20 3.0814 no . 2_566 H27 C21 3.3407 no . 2_566 H27 H10 3.4743 no . 2_567 H27 H11 2.6559 no . 2_567 H27 H18 3.3176 no . 1_546 H27 H20 3.0442 no . 2_566 H27 H21 3.4577 no . 2_566 H28 C10 3.4808 no . 2_567 H28 C17 3.0132 no . 2_566 H28 C18 3.2069 no . 2_566 H28 C19 3.3013 no . 2_566 H28 C20 3.2495 no . 2_566 H28 C21 3.0412 no . 2_566 H28 C22 2.9132 no . 2_566 H28 H10 2.8372 no . 2_567 H28 H18 3.4484 no . 1_546 H28 H19 3.2701 no . 1_546 H28 H21 3.5078 no . 2_566 H28 H22 3.3252 no . 2_566 data_y_cf3an_thio_3 _database_code_depnum_ccdc_archive 'CCDC 924506' #TrackingRef '17757_web_deposit_cif_file_2_TakashiYamazaki_1360897912.Comp.3o.cif' _audit_creation_date 2012-12-27 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C24 H12 F6 S2' _chemical_formula_sum 'C24 H14 F6 S2' _chemical_formula_weight 480.47 _chemical_melting_point ? 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.785(5) _cell_length_b 5.4006(13) _cell_length_c 16.888(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.112(4) _cell_angle_gamma 90.00 _cell_volume 1926.9(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2104 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 30.81 _cell_measurement_theta_min 2.49 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_correction_T_min 0.4680 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1356 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.6272. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 976 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_unetI/netI 0.0449 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5295 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.93 _diffrn_ambient_temperature 296.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 1649 _reflns_number_total 1955 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.540 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.069 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.238 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 1955 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0510 _refine_ls_restrained_S_all 1.238 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.012 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1536 _refine_ls_wR_factor_ref 0.1636 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H9 of C9, H10 of C10, H11 of C11, H2 of C2, H13 of C13, H1 of C1, H5 of C5 2. Uiso/Uaniso restraints and constraints Uanis(S2) = Uanis(S1) Uanis(C14) = Uanis(C12) Uiso(C2) = Uiso(C13) 3. Others Sof(S1)=1-Sof(S2)=Sof(C2)=Sof(H2)=1-Sof(S2)=1-Sof(S2) Sof(F1)=Sof(F2)=Sof(F3)=Sof(C12)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2)=1-Sof(F2) 4.a Aromatic/amide H refined with riding coordinates: C1(H1), C5(H5), C9(H9), C10(H10), C11(H11), C2(H2), C13(H13) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 S1 S 0.78228(4) 0.69637(19) 0.91260(6) 0.0320(3) Uani 0.777(2) 1 d P A 1 F1 F 0.8863(8) -0.137(3) 1.1189(10) 0.039(3) Uani 0.402(14) 1 d P A 1 F2 F 0.9575(4) 0.0872(17) 1.1915(6) 0.0306(17) Uani 0.402(14) 1 d P A 1 F3 F 0.8853(6) 0.2560(16) 1.1091(4) 0.047(3) Uani 0.402(14) 1 d P A 1 C1 C 0.78678(11) 1.0540(4) 0.81764(14) 0.0296(6) Uani 1 1 d . . . H1 H 0.7756 1.1964 0.7865 0.036 Uiso 1 1 calc R A 1 S2 S 0.84556(18) 0.9294(8) 0.8048(3) 0.0320(3) Uani 0.223(2) 1 d P A 2 C3 C 0.84678(10) 0.7057(4) 0.87281(12) 0.0193(5) Uani 1 1 d . . . C4 C 0.89684(9) 0.5201(4) 0.89373(11) 0.0183(5) Uani 1 1 d . A . C5 C 0.90341(9) 0.3703(4) 0.96073(11) 0.0178(4) Uani 1 1 d . . . H5 H 0.8756 0.3919 0.9941 0.021 Uiso 1 1 calc R A . C6 C 0.95064(9) 0.1832(4) 0.98190(11) 0.0157(4) Uani 1 1 d . A . C7 C 0.95682(9) 0.0229(4) 1.04970(12) 0.0192(5) Uani 1 1 d . . . C8 C 0.99508(9) 0.1570(4) 0.93150(11) 0.0164(4) Uani 1 1 d . . . C9 C 0.98687(9) 0.3188(4) 0.86204(12) 0.0200(5) Uani 1 1 d . A . H9 H 1.0147 0.3046 0.8284 0.024 Uiso 1 1 calc R . . C10 C 0.94067(9) 0.4895(4) 0.84374(12) 0.0223(5) Uani 1 1 d . . . H10 H 0.9372 0.5891 0.7979 0.027 Uiso 1 1 calc R A . C11 C 0.75262(12) 0.9571(5) 0.86689(16) 0.0356(6) Uani 1 1 d . A . H11 H 0.7158 1.0298 0.8745 0.043 Uiso 1 1 calc R B 1 C12 C 0.9215(8) 0.063(3) 1.1169(11) 0.0212(16) Uani 0.402(14) 1 d P A 1 C2 C 0.84228(16) 0.9112(7) 0.8193(2) 0.0146(8) Uiso 0.777(2) 1 d P A 1 H2 H 0.8716 0.9480 0.7892 0.017 Uiso 0.777(2) 1 calc PR A 1 C13 C 0.7966(6) 0.757(3) 0.9229(9) 0.0146(8) Uiso 0.223(2) 1 d P A 2 H13 H 0.7933 0.6892 0.9723 0.017 Uiso 0.223(2) 1 calc PR A 2 F2 F 0.8545(3) 0.1446(16) 1.0720(6) 0.068(3) Uani 0.598(14) 1 d P A 2 F3 F 0.9350(5) 0.0958(17) 1.1758(5) 0.064(2) Uani 0.598(14) 1 d P A 2 F5 F 0.8849(5) -0.2095(15) 1.1096(6) 0.0271(14) Uani 0.598(14) 1 d P A 2 C14 C 0.9072(5) 0.017(2) 1.0997(7) 0.0212(16) Uani 0.598(14) 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 S1 0.0325(6) 0.0366(7) 0.0317(5) 0.0107(4) 0.0170(4) 0.0154(4) F1 0.036(3) 0.047(7) 0.040(3) -0.006(4) 0.021(2) -0.024(5) F2 0.047(3) 0.076(4) 0.102(5) 0.067(4) 0.057(3) 0.044(3) F2 0.054(4) 0.026(3) 0.017(2) -0.001(2) 0.016(3) -0.007(3) F3 0.089(5) 0.079(4) 0.041(4) -0.038(3) 0.051(4) -0.046(4) F3 0.065(5) 0.053(4) 0.044(3) 0.025(3) 0.049(3) 0.040(4) C1 0.0364(12) 0.0203(12) 0.0243(11) -0.0005(8) -0.0076(9) 0.0003(9) S2 0.0325(6) 0.0366(7) 0.0317(5) 0.0107(4) 0.0170(4) 0.0154(4) C3 0.0205(10) 0.0211(11) 0.0155(9) -0.0012(8) 0.0027(8) 0.0011(8) C4 0.0186(10) 0.0210(11) 0.0141(9) -0.0007(8) 0.0019(7) 0.0005(8) C5 0.0185(9) 0.0210(11) 0.0148(9) -0.0020(8) 0.0055(7) 0.0010(8) C6 0.0170(9) 0.0186(11) 0.0109(8) -0.0023(7) 0.0021(7) -0.0004(8) C7 0.0211(10) 0.0224(11) 0.0170(10) 0.0002(8) 0.0104(8) 0.0014(8) C8 0.0186(9) 0.0185(10) 0.0122(9) -0.0020(7) 0.0040(7) -0.0013(8) C9 0.0198(10) 0.0277(12) 0.0143(9) 0.0024(8) 0.0074(8) 0.0002(8) C10 0.0244(11) 0.0268(12) 0.0166(10) 0.0071(8) 0.0068(8) 0.0021(9) C11 0.0295(12) 0.0377(15) 0.0407(14) -0.0044(11) 0.0109(10) 0.0118(11) C12 0.026(5) 0.020(5) 0.021(5) 0.002(3) 0.012(3) 0.004(3) F5 0.0217(18) 0.033(4) 0.029(3) 0.008(2) 0.0099(16) -0.006(2) C14 0.026(5) 0.020(5) 0.021(5) 0.002(3) 0.012(3) 0.004(3) _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 S1 C3 1.700(2) . ? S1 C11 1.659(3) . ? F1 C12 1.331(19) . ? F2 C12 1.317(15) . ? F2 C14 1.324(11) . ? F3 C12 1.295(19) . ? F3 C14 1.350(10) . ? C1 H1 0.9300 . ? C1 S2 1.509(4) . ? C1 C11 1.350(4) . ? C1 C2 1.429(4) . ? S2 C3 1.663(5) . ? C3 C4 1.460(3) . ? C3 C2 1.419(4) . ? C3 C13 1.562(15) . ? C4 C5 1.370(3) . ? C4 C10 1.430(3) . ? C5 H5 0.9300 . ? C5 C6 1.424(3) . ? C6 C7 1.416(3) . ? C6 C8 1.443(3) . ? C7 C8 1.407(3) 5_757 ? C7 C12 1.53(2) . ? C7 C14 1.527(12) . ? C8 C7 1.407(3) 5_757 ? C8 C9 1.438(3) . ? C9 H9 0.9300 . ? C9 C10 1.344(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C11 C13 1.592(15) . ? C2 H2 0.9300 . ? C13 H13 0.9300 . ? F5 C14 1.339(12) . ? 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 C11 S1 C3 93.24(12) . . ? S2 C1 H1 113.7 . . ? C11 C1 H1 124.1 . . ? C11 C1 S2 122.1(3) . . ? C11 C1 C2 111.7(2) . . ? C2 C1 H1 124.1 . . ? C2 C1 S2 10.8(2) . . ? C1 S2 C3 95.5(2) . . ? S2 C3 S1 114.79(17) . . ? C4 C3 S1 121.64(16) . . ? C4 C3 S2 123.4(2) . . ? C4 C3 C13 124.9(6) . . ? C2 C3 S1 109.86(19) . . ? C2 C3 S2 5.8(2) . . ? C2 C3 C4 128.5(2) . . ? C2 C3 C13 104.9(6) . . ? C13 C3 S1 15.4(5) . . ? C13 C3 S2 110.5(6) . . ? C5 C4 C3 121.79(19) . . ? C5 C4 C10 117.98(19) . . ? C10 C4 C3 120.23(18) . . ? C4 C5 H5 118.3 . . ? C4 C5 C6 123.36(19) . . ? C6 C5 H5 118.3 . . ? C5 C6 C8 117.98(18) . . ? C7 C6 C5 123.87(19) . . ? C7 C6 C8 118.15(19) . . ? C6 C7 C12 123.1(8) . . ? C6 C7 C14 121.4(5) . . ? C8 C7 C6 121.56(18) 5_757 . ? C8 C7 C12 114.2(7) 5_757 . ? C8 C7 C14 116.7(5) 5_757 . ? C14 C7 C12 16.8(5) . . ? C7 C8 C6 120.29(18) 5_757 . ? C7 C8 C9 122.74(18) 5_757 . ? C9 C8 C6 116.96(18) . . ? C8 C9 H9 118.6 . . ? C10 C9 C8 122.77(18) . . ? C10 C9 H9 118.6 . . ? C4 C10 H10 119.5 . . ? C9 C10 C4 120.92(18) . . ? C9 C10 H10 119.5 . . ? S1 C11 H11 123.1 . . ? C1 C11 S1 113.90(18) . . ? C1 C11 H11 123.0 . . ? C1 C11 C13 106.7(6) . . ? C13 C11 S1 16.0(4) . . ? C13 C11 H11 128.2 . . ? F1 C12 C7 107.5(12) . . ? F2 C12 F1 105.6(17) . . ? F2 C12 C7 115.6(12) . . ? F3 C12 F1 108.4(14) . . ? F3 C12 F2 102.8(11) . . ? F3 C12 C7 116.2(15) . . ? C1 C2 H2 124.4 . . ? C3 C2 C1 111.2(3) . . ? C3 C2 H2 124.4 . . ? C3 C13 C11 101.4(9) . . ? C3 C13 H13 129.3 . . ? C11 C13 H13 129.3 . . ? F2 C14 F3 108.7(8) . . ? F2 C14 C7 117.6(9) . . ? F3 C14 C7 107.8(6) . . ? F5 C14 F2 102.2(7) . . ? F5 C14 F3 105.2(10) . . ? F5 C14 C7 114.6(9) . . ? data_User-defined2 _database_code_depnum_ccdc_archive 'CCDC 924507' #TrackingRef '17758_web_deposit_cif_file_3_TakashiYamazaki_1360897912.Comp.3q.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 11.8145 _cell_length_b 8.9218 _cell_length_c 12.4651 _cell_angle_alpha 90 _cell_angle_beta 95.06 _cell_angle_gamma 90 _cell_volume 1308.78 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z F3 F 0.61607 2.02739 0.779849 F4 F 0.443564 2.08456 0.778883 F5 F 0.564536 2.23879 0.730882 O1 O 0.89739 0.793898 0.393025 C1 C 0.537339 1.85534 0.470503 C2 C 0.755715 1.20693 0.45504 C5 C 0.54132 1.89726 0.581484 C6 C 0.50989 2.04331 0.608465 C7 C 0.852041 0.928064 0.419603 C8 C 0.584112 1.71311 0.443764 C9 C 0.708719 1.35331 0.475738 C10 C 0.764913 1.15459 0.351065 C12 C 0.812725 1.01796 0.333669 C13 C 0.669978 1.47067 0.493295 C14 C 0.842111 0.977157 0.5239 C15 C 0.621981 1.61268 0.520517 C16 C 0.795008 1.11547 0.540732 C17 C 0.531414 2.09655 0.723312 C18 C 0.573606 1.78271 0.660089 C19 C 0.610368 1.64642 0.630371 C21 C 0.934828 0.695487 0.478798 H1 H 0.590037 1.68935 0.371924 H2 H 0.738104 1.21231 0.292192 H3 H 0.820338 0.98646 0.263601 H4 H 0.868275 0.917752 0.582209 H5 H 0.790365 1.14865 0.610881 H6 H 0.568779 1.80266 0.732815 H7 H 0.629497 1.57479 0.683123 H8 H 0.873243 0.670941 0.521 H9 H 0.964677 0.605259 0.450288 H10 H 0.993583 0.745365 0.523497 F3 F 0.383947 1.97258 0.220191 F4 F 0.556368 1.91542 0.221157 F5 F 0.435473 1.76119 0.269077 O1 O 0.102627 3.20608 0.607015 C1 C 0.46267 2.14475 0.529457 C2 C 0.244302 2.79305 0.545001 C5 C 0.458689 2.10271 0.418475 C6 C 0.490119 1.95667 0.391495 C7 C 0.147976 3.07191 0.580437 C8 C 0.415897 2.28687 0.556195 C9 C 0.291298 2.64666 0.524302 C10 C 0.235096 2.84539 0.648895 C12 C 0.187285 2.98202 0.666291 C13 C 0.330031 2.52931 0.506665 C14 C 0.157898 3.02282 0.47606 C15 C 0.378036 2.3873 0.479523 C16 C 0.205008 2.88451 0.459308 C17 C 0.468603 1.90354 0.276729 C18 C 0.426403 2.21727 0.33987 C19 C 0.389642 2.35356 0.369589 C21 C 0.0651811 3.30449 0.521161 H1 H 0.40998 2.31074 0.628116 H2 H 0.261906 2.78767 0.707768 H3 H 0.179678 3.01352 0.736439 H4 H 0.131742 3.08234 0.417831 H5 H 0.20956 2.85133 0.389079 H6 H 0.431238 2.19731 0.267225 H7 H 0.370519 2.42518 0.316917 H8 H 0.126774 3.32915 0.47904 H9 H 0.0353321 3.39472 0.549672 H10 H 0.00642672 3.25461 0.476463 data_new _database_code_depnum_ccdc_archive 'CCDC 924508' #TrackingRef '17759_web_deposit_cif_file_4_TakashiYamazaki_1360897912.Comp.6aB.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H8 F16' _chemical_formula_weight 564.27 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 ? _symmetry_space_group_name_H-M ? 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 15.259(4) _cell_length_b 11.705(3) _cell_length_c 12.681(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.096(5) _cell_angle_gamma 90.00 _cell_volume 2083.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16397 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3517 _reflns_number_gt 2872 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0799P)^2^+1.4052P] 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 3517 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1433 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 F5 F 0.23232(12) 0.25481(15) 0.59731(14) 0.0286(4) Uani 1 1 d . . . F4 F 0.29166(12) 0.17986(14) 0.48435(14) 0.0279(4) Uani 1 1 d . . . F3 F 0.68616(13) 0.53951(17) 0.79963(16) 0.0418(5) Uani 1 1 d . . . F6 F 0.22911(12) 0.39953(17) 0.35596(16) 0.0378(5) Uani 1 1 d . . . F2 F 0.65338(13) 0.42614(18) 0.91171(14) 0.0397(5) Uani 1 1 d . . . F8 F 0.16170(13) 0.19777(18) 0.27490(16) 0.0403(5) Uani 1 1 d . . . F9 F 0.09253(14) 0.17694(17) 0.39505(16) 0.0411(5) Uani 1 1 d . . . F7 F 0.14148(13) 0.41213(16) 0.45526(16) 0.0376(5) Uani 1 1 d . . . F10 F 0.04855(15) 0.4048(2) 0.20538(18) 0.0555(6) Uani 1 1 d . . . F1 F 0.70513(14) 0.3585(2) 0.79232(17) 0.0519(6) Uani 1 1 d . . . F13 F -0.03060(18) 0.1227(2) 0.1780(2) 0.0667(7) Uani 1 1 d . . . F11 F -0.03153(14) 0.3355(2) 0.29817(19) 0.0581(7) Uani 1 1 d . . . F12 F 0.01880(17) 0.2280(3) 0.07158(19) 0.0717(8) Uani 1 1 d . . . C3 C 0.6027(2) 0.3768(3) 0.5624(3) 0.0251(7) Uani 1 1 d . . . C6 C 0.4223(2) 0.2939(3) 0.4263(3) 0.0230(7) Uani 1 1 d . . . C7 C 0.4359(2) 0.3405(2) 0.5365(2) 0.0203(6) Uani 1 1 d . . . C2 C 0.5299(2) 0.3812(2) 0.6069(2) 0.0212(6) Uani 1 1 d . . . C9 C 0.3748(2) 0.4219(2) 0.6726(2) 0.0224(7) Uani 1 1 d . . . C14 C 0.4694(2) 0.4603(2) 0.7438(2) 0.0229(7) Uani 1 1 d . . . F15 F -0.16434(18) 0.2000(3) -0.0237(2) 0.0823(9) Uani 1 1 d . . . C8 C 0.3626(2) 0.3512(2) 0.5775(2) 0.0210(6) Uani 1 1 d . . . C1 C 0.5464(2) 0.4274(2) 0.7160(2) 0.0238(7) Uani 1 1 d . . . C4 C 0.5845(2) 0.3367(2) 0.4558(3) 0.0243(7) Uani 1 1 d . . . C13 C 0.4807(2) 0.5352(3) 0.8384(3) 0.0289(7) Uani 1 1 d . . . C18 C 0.1899(2) 0.3387(3) 0.4161(3) 0.0260(7) Uani 1 1 d . . . C5 C 0.4933(2) 0.2947(3) 0.3869(3) 0.0253(7) Uani 1 1 d . . . C10 C 0.2978(2) 0.4599(3) 0.7021(3) 0.0278(7) Uani 1 1 d . . . C17 C 0.2712(2) 0.2822(3) 0.5206(2) 0.0233(7) Uani 1 1 d . . . C19 C 0.1179(2) 0.2533(3) 0.3337(3) 0.0290(7) Uani 1 1 d . . . C11 C 0.3127(3) 0.5306(3) 0.7921(3) 0.0349(8) Uani 1 1 d . . . C15 C 0.6477(2) 0.4389(3) 0.8038(3) 0.0293(7) Uani 1 1 d . . . C20 C 0.0262(2) 0.3075(3) 0.2453(3) 0.0362(8) Uani 1 1 d . . . C12 C 0.4054(3) 0.5688(3) 0.8609(3) 0.0343(8) Uani 1 1 d . . . F16 F -0.1343(2) 0.3729(3) 0.0425(3) 0.1075(13) Uani 1 1 d . . . F14 F -0.18528(19) 0.2506(4) 0.1265(3) 0.1083(13) Uani 1 1 d . . . C21 C -0.0281(3) 0.2292(4) 0.1426(3) 0.0457(10) Uani 1 1 d . . . C22 C -0.1300(3) 0.2658(5) 0.0685(4) 0.0701(14) Uani 1 1 d . . . H10 H 0.235(2) 0.438(3) 0.653(3) 0.021(8) Uiso 1 1 d . . . H6 H 0.364(2) 0.268(2) 0.379(2) 0.012(7) Uiso 1 1 d . . . H13 H 0.549(3) 0.566(3) 0.889(3) 0.037(9) Uiso 1 1 d . . . H5 H 0.479(2) 0.267(3) 0.303(3) 0.026(8) Uiso 1 1 d . . . H11 H 0.258(3) 0.557(3) 0.803(3) 0.038(10) Uiso 1 1 d . . . H3 H 0.663(2) 0.412(3) 0.602(3) 0.022(8) Uiso 1 1 d . . . H12 H 0.411(3) 0.617(4) 0.911(4) 0.058(13) Uiso 1 1 d . . . H4 H 0.632(2) 0.339(3) 0.427(3) 0.029(9) 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 F5 0.0295(10) 0.0287(10) 0.0297(10) 0.0020(7) 0.0138(8) -0.0047(8) F4 0.0286(10) 0.0200(9) 0.0327(10) -0.0027(7) 0.0095(8) -0.0028(7) F3 0.0361(11) 0.0463(13) 0.0330(11) 0.0034(9) 0.0026(9) -0.0219(9) F6 0.0268(10) 0.0416(12) 0.0376(11) 0.0151(9) 0.0047(8) -0.0061(9) F2 0.0356(11) 0.0562(14) 0.0194(10) 0.0079(8) 0.0022(8) -0.0055(9) F8 0.0323(11) 0.0525(13) 0.0342(11) -0.0123(9) 0.0110(9) 0.0025(9) F9 0.0381(11) 0.0442(13) 0.0382(11) -0.0011(9) 0.0120(9) -0.0181(9) F7 0.0318(11) 0.0351(11) 0.0372(11) -0.0068(8) 0.0043(8) 0.0082(9) F10 0.0393(12) 0.0516(14) 0.0515(13) 0.0118(11) -0.0081(10) -0.0017(10) F1 0.0346(11) 0.0619(15) 0.0406(12) -0.0104(10) -0.0054(9) 0.0196(11) F13 0.0647(16) 0.0481(16) 0.0587(15) -0.0051(12) -0.0067(12) -0.0159(12) F11 0.0276(11) 0.0881(19) 0.0527(14) -0.0196(12) 0.0094(10) 0.0072(11) F12 0.0466(14) 0.128(3) 0.0367(13) -0.0207(14) 0.0125(11) -0.0042(14) C3 0.0219(16) 0.0196(16) 0.0304(17) 0.0034(13) 0.0064(13) -0.0009(13) C6 0.0248(17) 0.0168(15) 0.0229(15) -0.0005(12) 0.0045(13) -0.0001(13) C7 0.0238(15) 0.0143(15) 0.0208(15) 0.0033(11) 0.0065(12) 0.0011(12) C2 0.0264(16) 0.0120(15) 0.0227(15) 0.0027(11) 0.0068(13) 0.0021(12) C9 0.0274(16) 0.0185(16) 0.0204(15) 0.0051(12) 0.0085(13) 0.0006(13) C14 0.0301(17) 0.0163(16) 0.0202(15) 0.0027(11) 0.0077(13) -0.0017(12) F15 0.0489(15) 0.100(2) 0.0630(16) -0.0286(16) -0.0157(13) -0.0059(15) C8 0.0241(16) 0.0152(15) 0.0199(15) 0.0032(11) 0.0045(12) 0.0009(12) C1 0.0283(17) 0.0156(15) 0.0218(15) 0.0023(12) 0.0039(13) -0.0019(13) C4 0.0263(17) 0.0167(16) 0.0327(17) 0.0044(13) 0.0144(14) 0.0014(13) C13 0.038(2) 0.0215(17) 0.0228(16) -0.0014(12) 0.0076(14) -0.0057(14) C18 0.0227(16) 0.0258(17) 0.0294(17) 0.0014(13) 0.0100(13) -0.0006(13) C5 0.0327(17) 0.0182(16) 0.0251(16) 0.0014(12) 0.0115(14) 0.0016(13) C10 0.0298(18) 0.0270(18) 0.0271(17) 0.0037(13) 0.0119(15) 0.0025(14) C17 0.0271(16) 0.0205(16) 0.0235(15) -0.0010(12) 0.0112(13) -0.0025(13) C19 0.0261(17) 0.0335(19) 0.0267(16) -0.0033(13) 0.0098(14) -0.0026(14) C11 0.046(2) 0.031(2) 0.0346(19) -0.0012(15) 0.0230(17) 0.0029(16) C15 0.0278(17) 0.0304(18) 0.0254(17) -0.0001(13) 0.0057(14) -0.0044(15) C20 0.0268(18) 0.042(2) 0.0384(19) -0.0032(16) 0.0110(15) -0.0048(16) C12 0.053(2) 0.0246(19) 0.0291(18) -0.0039(15) 0.0203(17) -0.0019(16) F16 0.0649(19) 0.072(2) 0.114(3) 0.0028(19) -0.0415(17) 0.0103(16) F14 0.0354(15) 0.167(4) 0.115(3) -0.053(2) 0.0209(17) -0.0168(18) C21 0.031(2) 0.056(3) 0.041(2) -0.0050(18) 0.0043(17) -0.0033(18) C22 0.036(2) 0.079(4) 0.069(3) -0.017(3) -0.008(2) -0.007(2) _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 F5 C17 1.362(3) . ? F4 C17 1.363(3) . ? F3 C15 1.326(4) . ? F6 C18 1.343(3) . ? F2 C15 1.345(4) . ? F8 C19 1.347(4) . ? F9 C19 1.338(4) . ? F7 C18 1.349(4) . ? F10 C20 1.344(4) . ? F1 C15 1.332(4) . ? F13 C21 1.331(5) . ? F11 C20 1.340(4) . ? F12 C21 1.352(4) . ? C3 C4 1.354(4) . ? C3 C2 1.431(4) . ? C6 C5 1.360(4) . ? C6 C7 1.437(4) . ? C7 C8 1.411(4) . ? C7 C2 1.440(4) . ? C2 C1 1.413(4) . ? C9 C8 1.414(4) . ? C9 C10 1.437(4) . ? C9 C14 1.441(4) . ? C14 C1 1.407(4) . ? C14 C13 1.441(4) . ? F15 C22 1.324(5) . ? C8 C17 1.527(4) . ? C1 C15 1.515(4) . ? C4 C5 1.410(4) . ? C13 C12 1.347(5) . ? C18 C19 1.549(4) . ? C18 C17 1.562(4) . ? C10 C11 1.355(5) . ? C19 C20 1.546(5) . ? C11 C12 1.411(5) . ? C20 C21 1.542(5) . ? F16 C22 1.291(6) . ? F14 C22 1.331(6) . ? C21 C22 1.529(6) . ? 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 C4 C3 C2 121.4(3) . . ? C5 C6 C7 121.6(3) . . ? C8 C7 C6 124.0(3) . . ? C8 C7 C2 118.8(3) . . ? C6 C7 C2 117.2(3) . . ? C1 C2 C3 122.1(3) . . ? C1 C2 C7 119.1(3) . . ? C3 C2 C7 118.8(3) . . ? C8 C9 C10 123.8(3) . . ? C8 C9 C14 118.7(3) . . ? C10 C9 C14 117.4(3) . . ? C1 C14 C13 122.4(3) . . ? C1 C14 C9 119.2(3) . . ? C13 C14 C9 118.3(3) . . ? C7 C8 C9 120.6(3) . . ? C7 C8 C17 119.3(2) . . ? C9 C8 C17 120.1(2) . . ? C14 C1 C2 120.2(3) . . ? C14 C1 C15 120.2(3) . . ? C2 C1 C15 119.5(3) . . ? C3 C4 C5 120.3(3) . . ? C12 C13 C14 121.3(3) . . ? F6 C18 F7 107.6(3) . . ? F6 C18 C19 108.4(2) . . ? F7 C18 C19 108.3(2) . . ? F6 C18 C17 108.9(2) . . ? F7 C18 C17 109.0(2) . . ? C19 C18 C17 114.6(3) . . ? C6 C5 C4 120.7(3) . . ? C11 C10 C9 121.6(3) . . ? F5 C17 F4 104.8(2) . . ? F5 C17 C8 111.1(2) . . ? F4 C17 C8 109.6(2) . . ? F5 C17 C18 106.4(2) . . ? F4 C17 C18 107.3(2) . . ? C8 C17 C18 116.8(2) . . ? F9 C19 F8 108.6(3) . . ? F9 C19 C20 108.0(3) . . ? F8 C19 C20 107.5(2) . . ? F9 C19 C18 109.3(2) . . ? F8 C19 C18 108.1(2) . . ? C20 C19 C18 115.2(3) . . ? C10 C11 C12 120.7(3) . . ? F3 C15 F1 107.6(3) . . ? F3 C15 F2 106.6(2) . . ? F1 C15 F2 104.5(3) . . ? F3 C15 C1 112.9(3) . . ? F1 C15 C1 112.5(3) . . ? F2 C15 C1 112.2(3) . . ? F11 C20 F10 107.2(3) . . ? F11 C20 C21 109.1(3) . . ? F10 C20 C21 108.5(3) . . ? F11 C20 C19 108.9(3) . . ? F10 C20 C19 109.2(3) . . ? C21 C20 C19 113.7(3) . . ? C13 C12 C11 120.6(3) . . ? F13 C21 F12 107.9(3) . . ? F13 C21 C22 108.2(4) . . ? F12 C21 C22 105.7(3) . . ? F13 C21 C20 110.4(3) . . ? F12 C21 C20 108.6(3) . . ? C22 C21 C20 115.6(4) . . ? F16 C22 F15 112.1(5) . . ? F16 C22 F14 106.9(5) . . ? F15 C22 F14 107.0(4) . . ? F16 C22 C21 111.5(4) . . ? F15 C22 C21 109.5(4) . . ? F14 C22 C21 109.6(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.499 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.063 data_new2 _database_code_depnum_ccdc_archive 'CCDC 924509' #TrackingRef '17760_web_deposit_cif_file_5_TakashiYamazaki_1360897912.Comp.6aC.cif' _audit_creation_date 2012-12-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H8 F20' _chemical_formula_sum 'C23 H8 F20' _chemical_formula_weight 664.29 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 28.388(9) _cell_length_b 5.7555(15) _cell_length_c 14.350(5) _cell_angle_alpha 90.00 _cell_angle_beta 76.509(5) _cell_angle_gamma 90.00 _cell_volume 2280.0(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 293(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1304 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1277 _diffrn_reflns_av_unetI/netI 0.0912 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 12771 _diffrn_reflns_theta_full 23.25 _diffrn_reflns_theta_max 23.25 _diffrn_reflns_theta_min 3.57 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2501 _reflns_number_total 3252 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.287 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.062 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 420 _refine_ls_number_reflns 3252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0634 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1545 _refine_ls_wR_factor_ref 0.1730 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 F4 F 0.24201(8) 0.7245(4) 0.56771(18) 0.0256(6) Uani 1 1 d . . . F10 F 0.20007(9) 1.2483(4) 0.8359(2) 0.0391(7) Uani 1 1 d . . . F7 F 0.22521(9) 1.3035(4) 0.6311(2) 0.0337(7) Uani 1 1 d . . . F6 F 0.26966(9) 1.0898(4) 0.70236(19) 0.0332(7) Uani 1 1 d . . . F8 F 0.20058(9) 0.7771(4) 0.75367(19) 0.0336(7) Uani 1 1 d . . . F11 F 0.13879(10) 1.3025(4) 0.7721(2) 0.0398(8) Uani 1 1 d . . . F5 F 0.23209(9) 1.0305(4) 0.49042(18) 0.0294(6) Uani 1 1 d . . . F9 F 0.15630(9) 0.9388(4) 0.6659(2) 0.0355(7) Uani 1 1 d . . . F2 F 0.46525(10) 0.9364(5) 0.2828(2) 0.0435(8) Uani 1 1 d . . . F1 F 0.49202(11) 1.0889(6) 0.3962(2) 0.0601(10) Uani 1 1 d . . . F3 F 0.48429(11) 0.7208(6) 0.3864(2) 0.0579(9) Uani 1 1 d . . . C14 C 0.39186(15) 0.7991(7) 0.5130(3) 0.0220(10) Uani 1 1 d . . . C10 C 0.32203(18) 0.6553(7) 0.6353(3) 0.0227(10) Uani 1 1 d . . . C8 C 0.31120(15) 0.9687(7) 0.5201(3) 0.0193(10) Uani 1 1 d . . . C3 C 0.4038(2) 1.3077(8) 0.3416(3) 0.0307(12) Uani 1 1 d . . . C13 C 0.42002(18) 0.6358(8) 0.5517(3) 0.0281(11) Uani 1 1 d . . . C2 C 0.38303(16) 1.1306(7) 0.4096(3) 0.0236(11) Uani 1 1 d . . . C19 C 0.16517(16) 1.1389(7) 0.8040(3) 0.0262(11) Uani 1 1 d . . . C1 C 0.41134(16) 0.9480(7) 0.4358(3) 0.0262(11) Uani 1 1 d . . . C6 C 0.30544(19) 1.3305(7) 0.4260(3) 0.0266(11) Uani 1 1 d . . . C9 C 0.34057(16) 0.8102(7) 0.5566(3) 0.0231(10) Uani 1 1 d . . . C7 C 0.33205(16) 1.1419(6) 0.4531(3) 0.0208(10) Uani 1 1 d . . . C5 C 0.3270(2) 1.4942(8) 0.3610(3) 0.0310(12) Uani 1 1 d . . . C11 C 0.35054(17) 0.5041(8) 0.6680(4) 0.0261(11) Uani 1 1 d . . . C12 C 0.40024(17) 0.4929(8) 0.6249(3) 0.0291(11) Uani 1 1 d . . . C4 C 0.37628(18) 1.4806(8) 0.3182(4) 0.0318(12) Uani 1 1 d . . . C16 C 0.25609(15) 0.9506(7) 0.5561(3) 0.0216(10) Uani 1 1 d . . . C18 C 0.18898(16) 0.9802(7) 0.7182(3) 0.0251(11) Uani 1 1 d . . . C17 C 0.23496(15) 1.0818(7) 0.6521(3) 0.0235(11) Uani 1 1 d . . . C15 C 0.46296(17) 0.9234(8) 0.3765(4) 0.0334(12) Uani 1 1 d . . . F12 F 0.10403(10) 0.8639(5) 0.8547(2) 0.0473(8) Uani 1 1 d . . . F13 F 0.16063(11) 0.8880(5) 0.9337(2) 0.0480(8) Uani 1 1 d . . . C21 C 0.09968(17) 1.1723(8) 0.9642(4) 0.0348(12) Uani 1 1 d . . . C20 C 0.13227(16) 1.0110(8) 0.8894(4) 0.0298(11) Uani 1 1 d . . . F15 F 0.12548(10) 1.3583(4) 0.9783(2) 0.0449(8) Uani 1 1 d . . . F14 F 0.06285(11) 1.2470(6) 0.9276(2) 0.0540(9) Uani 1 1 d . . . F17 F 0.11453(14) 1.0196(6) 1.1051(2) 0.0695(10) Uani 1 1 d . . . F16 F 0.05835(15) 0.8577(6) 1.0469(3) 0.0871(14) Uani 1 1 d . . . C23 C 0.0407(2) 1.2017(12) 1.1322(4) 0.0573(17) Uani 1 1 d . . . C22 C 0.0785(2) 1.0601(9) 1.0619(4) 0.0487(15) Uani 1 1 d . . . F19 F 0.05739(12) 1.4056(6) 1.1472(3) 0.0661(10) Uani 1 1 d . . . F20 F 0.02884(18) 1.0967(7) 1.2154(3) 0.1026(16) Uani 1 1 d . . . F18 F 0.00127(14) 1.2286(10) 1.1013(3) 0.1151(18) Uani 1 1 d . . . H11 H 0.3372(15) 0.417(7) 0.720(3) 0.019(11) Uiso 1 1 d . . . H10 H 0.2905(15) 0.667(6) 0.663(3) 0.009(10) Uiso 1 1 d . . . H6 H 0.2735(16) 1.352(6) 0.452(3) 0.015(11) Uiso 1 1 d . . . H3 H 0.4370(14) 1.299(6) 0.320(3) 0.003(10) Uiso 1 1 d . . . H13 H 0.4533(17) 0.617(7) 0.527(3) 0.024(12) Uiso 1 1 d . . . H4 H 0.3917(14) 1.590(7) 0.271(3) 0.011(10) Uiso 1 1 d . . . H5 H 0.3105(15) 1.616(7) 0.347(3) 0.019(12) Uiso 1 1 d . . . H12 H 0.4228(17) 0.386(7) 0.644(3) 0.030(12) 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 F4 0.0252(14) 0.0178(13) 0.0359(16) -0.0015(10) -0.0113(12) -0.0036(10) F10 0.0296(15) 0.0448(16) 0.0389(18) -0.0132(13) 0.0004(13) -0.0111(13) F7 0.0431(17) 0.0161(13) 0.0364(17) 0.0025(11) 0.0018(13) 0.0013(11) F6 0.0227(14) 0.0451(16) 0.0321(17) -0.0118(12) -0.0073(12) -0.0049(12) F8 0.0401(16) 0.0219(14) 0.0345(17) 0.0052(11) 0.0000(13) 0.0016(12) F11 0.0478(18) 0.0324(15) 0.0350(18) 0.0047(12) -0.0011(14) 0.0128(13) F5 0.0338(15) 0.0298(14) 0.0296(16) 0.0045(11) -0.0175(13) 0.0005(11) F9 0.0272(15) 0.0401(15) 0.0409(18) -0.0086(13) -0.0114(13) -0.0045(12) F2 0.0365(17) 0.0678(19) 0.0220(17) 0.0016(13) 0.0016(13) 0.0039(14) F1 0.0377(18) 0.091(2) 0.051(2) -0.0045(18) -0.0094(16) -0.0316(17) F3 0.0425(19) 0.073(2) 0.049(2) 0.0157(17) 0.0078(16) 0.0224(16) C14 0.025(2) 0.021(2) 0.022(3) -0.0068(19) -0.008(2) -0.0030(19) C10 0.019(3) 0.028(3) 0.022(3) -0.0036(19) -0.006(2) -0.003(2) C8 0.025(2) 0.017(2) 0.017(2) -0.0035(18) -0.0064(19) 0.0002(18) C3 0.035(3) 0.035(3) 0.020(3) 0.002(2) -0.001(2) -0.011(2) C13 0.026(3) 0.033(3) 0.025(3) -0.003(2) -0.005(2) 0.005(2) C2 0.029(3) 0.021(2) 0.023(3) -0.0050(19) -0.011(2) -0.008(2) C19 0.022(2) 0.025(2) 0.033(3) 0.002(2) -0.009(2) -0.001(2) C1 0.029(3) 0.029(2) 0.022(3) -0.004(2) -0.007(2) -0.004(2) C6 0.039(3) 0.020(3) 0.022(3) -0.0041(19) -0.010(2) -0.002(2) C9 0.030(3) 0.018(2) 0.023(3) -0.0046(18) -0.008(2) -0.0043(19) C7 0.034(3) 0.016(2) 0.014(2) -0.0033(17) -0.010(2) -0.0031(19) C5 0.054(3) 0.020(3) 0.022(3) -0.003(2) -0.014(3) 0.002(2) C11 0.030(3) 0.025(2) 0.026(3) 0.004(2) -0.013(2) -0.004(2) C12 0.028(3) 0.034(3) 0.029(3) -0.001(2) -0.015(2) 0.006(2) C4 0.044(3) 0.024(3) 0.029(3) 0.003(2) -0.010(3) -0.012(2) C16 0.026(2) 0.015(2) 0.028(3) 0.0013(18) -0.014(2) 0.0009(19) C18 0.028(3) 0.018(2) 0.031(3) 0.001(2) -0.012(2) -0.0010(19) C17 0.022(2) 0.013(2) 0.034(3) -0.0006(19) -0.004(2) -0.0023(18) C15 0.032(3) 0.044(3) 0.025(3) 0.008(2) -0.007(2) -0.008(3) F12 0.0424(18) 0.0445(17) 0.048(2) -0.0105(14) 0.0038(15) -0.0201(14) F13 0.058(2) 0.0474(17) 0.0351(19) 0.0099(14) -0.0029(16) 0.0178(15) C21 0.027(3) 0.036(3) 0.041(3) -0.006(2) -0.005(2) 0.001(2) C20 0.024(2) 0.030(3) 0.034(3) 0.002(2) -0.005(2) -0.007(2) F15 0.0440(17) 0.0349(16) 0.048(2) -0.0098(13) 0.0055(15) -0.0104(13) F14 0.0360(18) 0.078(2) 0.046(2) -0.0012(17) -0.0053(15) 0.0171(16) F17 0.094(3) 0.078(2) 0.034(2) 0.0021(17) -0.010(2) 0.027(2) F16 0.126(3) 0.061(2) 0.052(3) -0.0081(18) 0.024(2) -0.046(2) C23 0.043(4) 0.078(4) 0.041(4) -0.008(3) 0.009(3) -0.019(3) C22 0.053(4) 0.042(3) 0.043(4) -0.003(3) 0.002(3) -0.018(3) F19 0.056(2) 0.063(2) 0.064(3) -0.0189(18) 0.0168(18) -0.0039(17) F20 0.142(4) 0.088(3) 0.045(3) -0.001(2) 0.044(3) -0.032(3) F18 0.035(2) 0.218(5) 0.081(3) -0.051(3) 0.008(2) -0.002(3) _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 F4 C16 1.360(5) . ? F10 C19 1.342(5) . ? F7 C17 1.354(5) . ? F6 C17 1.351(5) . ? F8 C18 1.346(5) . ? F11 C19 1.348(5) . ? F5 C16 1.365(5) . ? F9 C18 1.344(5) . ? F2 C15 1.333(5) . ? F1 C15 1.334(5) . ? F3 C15 1.337(6) . ? C14 C13 1.427(6) . ? C14 C1 1.408(6) . ? C14 C9 1.446(6) . ? C10 C9 1.438(6) . ? C10 C11 1.345(6) . ? C8 C9 1.417(6) . ? C8 C7 1.415(6) . ? C8 C16 1.532(6) . ? C3 C2 1.439(6) . ? C3 C4 1.355(7) . ? C13 C12 1.349(7) . ? C2 C1 1.425(6) . ? C2 C7 1.438(6) . ? C19 C18 1.555(6) . ? C19 C20 1.544(6) . ? C1 C15 1.520(7) . ? C6 C7 1.428(6) . ? C6 C5 1.366(7) . ? C5 C4 1.393(7) . ? C11 C12 1.403(7) . ? C16 C17 1.563(6) . ? C18 C17 1.539(6) . ? F12 C20 1.339(5) . ? F13 C20 1.339(5) . ? C21 C20 1.551(7) . ? C21 F15 1.339(5) . ? C21 F14 1.345(6) . ? C21 C22 1.533(8) . ? F17 C22 1.335(7) . ? F16 C22 1.337(6) . ? C23 C22 1.527(8) . ? C23 F19 1.302(7) . ? C23 F20 1.309(7) . ? C23 F18 1.305(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 C13 C14 C9 117.4(4) . . ? C1 C14 C13 123.7(4) . . ? C1 C14 C9 119.0(4) . . ? C11 C10 C9 122.3(5) . . ? C9 C8 C16 118.3(4) . . ? C7 C8 C9 121.1(4) . . ? C7 C8 C16 120.6(4) . . ? C4 C3 C2 121.3(5) . . ? C12 C13 C14 122.4(5) . . ? C1 C2 C3 122.3(4) . . ? C1 C2 C7 119.4(4) . . ? C7 C2 C3 118.3(4) . . ? F10 C19 F11 107.5(3) . . ? F10 C19 C18 109.1(3) . . ? F10 C19 C20 108.1(4) . . ? F11 C19 C18 108.4(4) . . ? F11 C19 C20 108.8(4) . . ? C20 C19 C18 114.8(4) . . ? C14 C1 C2 121.0(4) . . ? C14 C1 C15 122.3(4) . . ? C2 C1 C15 116.7(4) . . ? C5 C6 C7 122.0(5) . . ? C10 C9 C14 117.3(4) . . ? C8 C9 C14 119.3(4) . . ? C8 C9 C10 123.4(4) . . ? C8 C7 C2 118.8(4) . . ? C8 C7 C6 123.8(4) . . ? C6 C7 C2 117.3(4) . . ? C6 C5 C4 120.4(5) . . ? C10 C11 C12 120.1(5) . . ? C13 C12 C11 120.5(5) . . ? C3 C4 C5 120.7(5) . . ? F4 C16 F5 103.1(3) . . ? F4 C16 C8 110.7(3) . . ? F4 C16 C17 108.2(3) . . ? F5 C16 C8 112.3(4) . . ? F5 C16 C17 107.2(3) . . ? C8 C16 C17 114.6(3) . . ? F8 C18 C19 108.1(4) . . ? F8 C18 C17 108.4(3) . . ? F9 C18 F8 108.6(3) . . ? F9 C18 C19 108.5(3) . . ? F9 C18 C17 108.6(4) . . ? C17 C18 C19 114.5(3) . . ? F7 C17 C16 108.4(4) . . ? F7 C17 C18 107.9(3) . . ? F6 C17 F7 107.4(3) . . ? F6 C17 C16 108.0(3) . . ? F6 C17 C18 107.6(4) . . ? C18 C17 C16 117.1(3) . . ? F2 C15 F1 106.7(4) . . ? F2 C15 F3 103.9(4) . . ? F2 C15 C1 111.9(4) . . ? F1 C15 F3 106.4(4) . . ? F1 C15 C1 112.2(4) . . ? F3 C15 C1 115.1(4) . . ? F15 C21 C20 108.9(4) . . ? F15 C21 F14 107.8(4) . . ? F15 C21 C22 108.1(4) . . ? F14 C21 C20 108.3(4) . . ? F14 C21 C22 108.5(4) . . ? C22 C21 C20 115.0(4) . . ? C19 C20 C21 114.6(4) . . ? F12 C20 C19 108.1(4) . . ? F12 C20 C21 108.9(4) . . ? F13 C20 C19 108.1(4) . . ? F13 C20 F12 108.7(4) . . ? F13 C20 C21 108.4(4) . . ? F19 C23 C22 111.3(5) . . ? F19 C23 F20 106.9(5) . . ? F19 C23 F18 108.9(6) . . ? F20 C23 C22 110.3(6) . . ? F18 C23 C22 111.4(5) . . ? F18 C23 F20 107.8(5) . . ? F17 C22 C21 108.7(4) . . ? F17 C22 F16 109.0(5) . . ? F17 C22 C23 106.4(5) . . ? F16 C22 C21 108.1(5) . . ? F16 C22 C23 108.0(5) . . ? C23 C22 C21 116.4(5) . . ?