# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # 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_xb5320_0m _database_code_depnum_ccdc_archive 'CCDC 903069' #TrackingRef 'xb5320_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H24 F8' _chemical_formula_weight 764.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.8049(17) _cell_length_b 12.2389(16) _cell_length_c 25.979(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.745(3) _cell_angle_gamma 90.00 _cell_volume 4281.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1159 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 16.85 _exptl_crystal_description blcok _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21161 _diffrn_reflns_av_R_equivalents 0.0818 _diffrn_reflns_av_sigmaI/netI 0.1327 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.05 _reflns_number_total 7514 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1600P)^2^+0.3028P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7514 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2033 _refine_ls_R_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.3356 _refine_ls_wR_factor_gt 0.2584 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3849(4) 0.1639(4) 0.2006(2) 0.0710(15) Uani 1 1 d . . . C2 C 0.3028(5) 0.2260(5) 0.2028(3) 0.094(2) Uani 1 1 d . . . C3 C 0.2154(5) 0.1852(6) 0.2085(3) 0.122(3) Uani 1 1 d . . . H3 H 0.1615 0.2304 0.2092 0.147 Uiso 1 1 calc R . . C4 C 0.2092(6) 0.0738(7) 0.2132(4) 0.127(3) Uani 1 1 d . . . C5 C 0.2858(6) 0.0070(6) 0.2126(3) 0.112(2) Uani 1 1 d . . . H5 H 0.2785 -0.0681 0.2158 0.135 Uiso 1 1 calc R . . C6 C 0.3763(5) 0.0504(5) 0.2073(3) 0.100(2) Uani 1 1 d . . . H6 H 0.4306 0.0049 0.2081 0.120 Uiso 1 1 calc R . . C7 C 0.4794(4) 0.2096(4) 0.1900(2) 0.0659(14) Uani 1 1 d . . . C8 C 0.5242(4) 0.1576(4) 0.1539(2) 0.0698(15) Uani 1 1 d . . . H8 H 0.4955 0.0945 0.1373 0.084 Uiso 1 1 calc R . . C9 C 0.6103(4) 0.1970(4) 0.1420(2) 0.0666(14) Uani 1 1 d . . . H9 H 0.6387 0.1617 0.1173 0.080 Uiso 1 1 calc R . . C10 C 0.6536(3) 0.2901(4) 0.16760(19) 0.0580(13) Uani 1 1 d . . . C11 C 0.6102(4) 0.3406(4) 0.20620(18) 0.0546(12) Uani 1 1 d . . . C12 C 0.5242(4) 0.3020(4) 0.21670(19) 0.0588(13) Uani 1 1 d . . . H12 H 0.4955 0.3368 0.2415 0.071 Uiso 1 1 calc R . . C13 C 0.7390(3) 0.3547(4) 0.16187(19) 0.0555(12) Uani 1 1 d . . . C14 C 0.8004(4) 0.3420(4) 0.1261(2) 0.0681(14) Uani 1 1 d . . . H14 H 0.7905 0.2851 0.1018 0.082 Uiso 1 1 calc R . . C15 C 0.8772(4) 0.4174(4) 0.1279(2) 0.0710(15) Uani 1 1 d . . . H15 H 0.9183 0.4099 0.1042 0.085 Uiso 1 1 calc R . . C16 C 0.8941(4) 0.5022(4) 0.1636(2) 0.0610(13) Uani 1 1 d . . . C17 C 0.8302(4) 0.5135(4) 0.19964(19) 0.0631(14) Uani 1 1 d . . . H17 H 0.8409 0.5693 0.2245 0.076 Uiso 1 1 calc R . . C18 C 0.7531(3) 0.4418(4) 0.19744(18) 0.0530(12) Uani 1 1 d . . . C19 C 0.9772(4) 0.5781(5) 0.1630(2) 0.0685(15) Uani 1 1 d . . . C20 C 1.0683(5) 0.5428(6) 0.1602(3) 0.0916(19) Uani 1 1 d . . . C21 C 1.1465(6) 0.6113(9) 0.1549(3) 0.120(3) Uani 1 1 d . . . H21 H 1.2084 0.5837 0.1531 0.145 Uiso 1 1 calc R . . C22 C 1.1274(6) 0.7201(8) 0.1526(3) 0.122(3) Uani 1 1 d . . . C23 C 1.0357(6) 0.7634(6) 0.1556(3) 0.109(2) Uani 1 1 d . . . H23 H 1.0247 0.8384 0.1543 0.131 Uiso 1 1 calc R . . C24 C 0.9612(4) 0.6906(5) 0.1605(2) 0.0830(17) Uani 1 1 d . . . H24 H 0.8990 0.7176 0.1622 0.100 Uiso 1 1 calc R . . C25 C 0.8277(4) 0.3081(4) 0.41644(19) 0.0634(14) Uani 1 1 d . . . C26 C 0.8937(5) 0.3448(6) 0.4608(2) 0.0867(18) Uani 1 1 d . . . C27 C 0.9436(5) 0.2751(8) 0.5002(3) 0.112(3) Uani 1 1 d . . . H27 H 0.9857 0.3027 0.5304 0.134 Uiso 1 1 calc R . . C28 C 0.9293(6) 0.1667(8) 0.4934(3) 0.107(2) Uani 1 1 d . . . C29 C 0.8675(5) 0.1256(6) 0.4500(3) 0.099(2) Uani 1 1 d . . . H29 H 0.8598 0.0504 0.4460 0.118 Uiso 1 1 calc R . . C30 C 0.8155(4) 0.1950(5) 0.4115(2) 0.0793(17) Uani 1 1 d . . . H30 H 0.7721 0.1660 0.3821 0.095 Uiso 1 1 calc R . . C31 C 0.7691(4) 0.3851(4) 0.3775(2) 0.0612(13) Uani 1 1 d . . . C32 C 0.7203(4) 0.4737(4) 0.3955(2) 0.0657(14) Uani 1 1 d . . . H32 H 0.7255 0.4821 0.4316 0.079 Uiso 1 1 calc R . . C33 C 0.6655(4) 0.5478(4) 0.3616(2) 0.0650(14) Uani 1 1 d . . . H33 H 0.6346 0.6062 0.3744 0.078 Uiso 1 1 calc R . . C34 C 0.6568(3) 0.5344(4) 0.3078(2) 0.0578(13) Uani 1 1 d . . . C35 C 0.6998(3) 0.4453(4) 0.28830(19) 0.0541(12) Uani 1 1 d . . . C36 C 0.7586(3) 0.3712(4) 0.32292(19) 0.0594(13) Uani 1 1 d . . . H36 H 0.7901 0.3136 0.3099 0.071 Uiso 1 1 calc R . . C37 C 0.6005(3) 0.5986(4) 0.26358(19) 0.0555(13) Uani 1 1 d . . . C38 C 0.5454(4) 0.6933(4) 0.2625(2) 0.0677(15) Uani 1 1 d . . . H38 H 0.5441 0.7314 0.2933 0.081 Uiso 1 1 calc R . . C39 C 0.4917(4) 0.7297(4) 0.2134(2) 0.0664(14) Uani 1 1 d . . . H39 H 0.4552 0.7940 0.2120 0.080 Uiso 1 1 calc R . . C40 C 0.4906(4) 0.6742(4) 0.16700(19) 0.0565(13) Uani 1 1 d . . . C41 C 0.5490(4) 0.5804(4) 0.1687(2) 0.0604(13) Uani 1 1 d . . . H41 H 0.5500 0.5421 0.1379 0.072 Uiso 1 1 calc R . . C42 C 0.6051(3) 0.5450(4) 0.21662(19) 0.0522(12) Uani 1 1 d . . . C43 C 0.4270(4) 0.7122(4) 0.1170(2) 0.0640(14) Uani 1 1 d . . . C44 C 0.4205(5) 0.8216(5) 0.1024(2) 0.0785(16) Uani 1 1 d . . . C45 C 0.3573(5) 0.8590(5) 0.0581(3) 0.095(2) Uani 1 1 d . . . H45 H 0.3532 0.9330 0.0499 0.114 Uiso 1 1 calc R . . C46 C 0.3003(6) 0.7842(7) 0.0263(3) 0.104(2) Uani 1 1 d . . . C47 C 0.3013(5) 0.6757(6) 0.0364(2) 0.094(2) Uani 1 1 d . . . H47 H 0.2607 0.6275 0.0137 0.113 Uiso 1 1 calc R . . C49 C 0.6703(3) 0.4420(4) 0.22824(18) 0.0520(12) Uani 1 1 d . . . F1 F 0.3094(3) 0.3339(4) 0.1991(2) 0.161(2) Uani 1 1 d . . . F2 F 0.1204(3) 0.0294(4) 0.2181(3) 0.184(2) Uani 1 1 d . . . F3 F 1.0887(3) 0.4350(4) 0.16391(19) 0.1265(15) Uani 1 1 d . . . F4 F 1.2020(4) 0.7891(4) 0.1475(2) 0.187(3) Uani 1 1 d . . . F5 F 0.9110(3) 0.4524(4) 0.46692(15) 0.1231(15) Uani 1 1 d . . . F6 F 0.9782(4) 0.1002(4) 0.53132(17) 0.159(2) Uani 1 1 d . . . F7 F 0.4767(4) 0.8924(4) 0.1302(2) 0.0978(17) Uani 0.65 1 d P . . F7' F 0.3651(6) 0.5411(8) 0.0923(4) 0.090(3) Uani 0.35 1 d P . . F8 F 0.2368(4) 0.8207(4) -0.01868(16) 0.1557(19) Uani 1 1 d . . . C48 C 0.3657(4) 0.6390(6) 0.0823(2) 0.0808(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.064(4) 0.065(4) 0.088(4) -0.014(3) 0.025(3) -0.006(3) C2 0.075(4) 0.051(4) 0.158(6) -0.018(4) 0.033(4) -0.009(3) C3 0.077(5) 0.088(5) 0.212(9) -0.033(5) 0.051(5) -0.014(4) C4 0.081(5) 0.110(6) 0.204(9) -0.038(6) 0.064(5) -0.032(5) C5 0.099(5) 0.075(4) 0.176(7) -0.014(5) 0.058(5) -0.019(4) C6 0.123(6) 0.077(4) 0.106(5) -0.010(4) 0.038(4) -0.052(4) C7 0.056(3) 0.056(3) 0.083(4) -0.004(3) 0.011(3) -0.002(3) C8 0.080(4) 0.057(3) 0.075(4) -0.015(3) 0.022(3) -0.005(3) C9 0.066(4) 0.062(3) 0.072(4) -0.015(3) 0.016(3) 0.002(3) C10 0.056(3) 0.055(3) 0.062(3) 0.002(3) 0.013(3) 0.007(3) C11 0.053(3) 0.056(3) 0.053(3) 0.000(2) 0.009(2) 0.005(2) C12 0.062(3) 0.048(3) 0.068(3) -0.003(2) 0.020(3) 0.003(3) C13 0.056(3) 0.058(3) 0.055(3) -0.003(2) 0.017(2) 0.005(3) C14 0.074(4) 0.062(3) 0.069(4) -0.008(3) 0.018(3) -0.002(3) C15 0.076(4) 0.075(4) 0.069(4) -0.001(3) 0.030(3) 0.005(3) C16 0.057(3) 0.062(3) 0.068(3) -0.005(3) 0.019(3) 0.001(3) C17 0.068(3) 0.060(3) 0.061(3) -0.011(3) 0.014(3) 0.002(3) C18 0.048(3) 0.051(3) 0.057(3) -0.002(2) 0.007(2) 0.002(2) C19 0.062(4) 0.074(4) 0.076(4) -0.010(3) 0.028(3) -0.008(3) C20 0.068(4) 0.092(5) 0.119(5) -0.024(4) 0.030(4) -0.004(4) C21 0.083(5) 0.150(8) 0.139(7) -0.049(6) 0.049(5) -0.022(5) C22 0.111(6) 0.127(7) 0.153(7) -0.047(6) 0.080(5) -0.049(6) C23 0.137(7) 0.089(5) 0.109(6) -0.022(4) 0.046(5) -0.013(5) C24 0.072(4) 0.090(5) 0.094(4) -0.012(4) 0.033(3) -0.026(4) C25 0.066(3) 0.070(4) 0.055(3) 0.001(3) 0.015(3) 0.008(3) C26 0.087(4) 0.093(5) 0.072(4) -0.020(4) 0.000(4) 0.004(4) C27 0.096(5) 0.153(8) 0.069(5) -0.007(5) -0.019(4) 0.030(5) C28 0.129(6) 0.123(7) 0.065(5) 0.004(5) 0.014(4) 0.035(5) C29 0.117(6) 0.086(5) 0.098(5) 0.020(4) 0.035(4) 0.027(4) C30 0.095(4) 0.070(4) 0.075(4) 0.003(3) 0.025(3) 0.015(3) C31 0.061(3) 0.062(3) 0.061(3) -0.005(3) 0.014(3) -0.004(3) C32 0.079(4) 0.067(3) 0.052(3) -0.006(3) 0.016(3) 0.001(3) C33 0.076(4) 0.062(3) 0.058(4) -0.013(3) 0.016(3) -0.003(3) C34 0.057(3) 0.054(3) 0.061(3) -0.010(3) 0.010(2) -0.005(3) C35 0.049(3) 0.055(3) 0.058(3) -0.004(2) 0.014(2) -0.002(2) C36 0.057(3) 0.060(3) 0.060(3) -0.004(3) 0.011(2) -0.004(3) C37 0.058(3) 0.046(3) 0.061(3) -0.004(2) 0.010(2) 0.004(2) C38 0.077(4) 0.059(3) 0.066(4) -0.013(3) 0.013(3) 0.010(3) C39 0.071(4) 0.052(3) 0.078(4) -0.001(3) 0.021(3) 0.013(3) C40 0.063(3) 0.049(3) 0.058(3) 0.002(2) 0.015(2) 0.004(2) C41 0.071(3) 0.051(3) 0.058(3) -0.004(2) 0.011(3) -0.003(3) C42 0.050(3) 0.048(3) 0.059(3) -0.007(2) 0.013(2) -0.002(2) C43 0.070(3) 0.060(3) 0.064(3) -0.003(3) 0.018(3) 0.005(3) C44 0.105(5) 0.057(4) 0.073(4) 0.003(3) 0.020(3) 0.009(4) C45 0.136(6) 0.067(4) 0.076(4) 0.014(4) 0.011(4) 0.025(4) C46 0.131(6) 0.103(6) 0.065(4) 0.009(4) -0.005(4) 0.042(5) C47 0.109(5) 0.089(5) 0.075(4) -0.003(4) -0.002(4) 0.007(4) C49 0.051(3) 0.053(3) 0.051(3) -0.006(2) 0.008(2) 0.000(2) F1 0.102(3) 0.104(3) 0.280(6) -0.008(4) 0.051(3) 0.006(3) F2 0.104(3) 0.132(4) 0.342(8) -0.042(4) 0.108(4) -0.049(3) F3 0.082(3) 0.111(3) 0.191(4) -0.016(3) 0.042(3) 0.017(2) F4 0.170(4) 0.177(5) 0.260(6) -0.095(4) 0.146(4) -0.114(4) F5 0.120(3) 0.106(3) 0.119(3) -0.027(2) -0.027(2) -0.011(2) F6 0.210(5) 0.167(4) 0.091(3) 0.040(3) 0.012(3) 0.094(4) F7 0.145(5) 0.050(3) 0.092(4) -0.005(3) 0.011(3) -0.009(3) F7' 0.090(7) 0.059(6) 0.103(7) 0.017(5) -0.021(5) -0.005(5) F8 0.209(5) 0.150(4) 0.085(3) 0.013(3) -0.018(3) 0.066(3) C48 0.082(4) 0.080(5) 0.077(4) 0.006(4) 0.010(3) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(8) . ? C1 C6 1.409(7) . ? C1 C7 1.500(7) . ? C2 F1 1.329(6) . ? C2 C3 1.344(8) . ? C3 C4 1.374(10) . ? C3 H3 0.9300 . ? C4 C5 1.338(9) . ? C4 F2 1.373(7) . ? C5 C6 1.393(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.386(7) . ? C7 C12 1.397(6) . ? C8 C9 1.379(7) . ? C8 H8 0.9300 . ? C9 C10 1.386(6) . ? C9 H9 0.9300 . ? C10 C11 1.419(6) . ? C10 C13 1.455(7) . ? C11 C12 1.360(6) . ? C11 C49 1.531(6) . ? C12 H12 0.9300 . ? C13 C18 1.396(6) . ? C13 C14 1.397(7) . ? C14 C15 1.398(7) . ? C14 H14 0.9300 . ? C15 C16 1.378(7) . ? C15 H15 0.9300 . ? C16 C17 1.427(7) . ? C16 C19 1.478(7) . ? C17 C18 1.372(6) . ? C17 H17 0.9300 . ? C18 C49 1.533(6) . ? C19 C20 1.347(8) . ? C19 C24 1.394(7) . ? C20 F3 1.347(7) . ? C20 C21 1.398(9) . ? C21 C22 1.357(10) . ? C21 H21 0.9300 . ? C22 F4 1.361(8) . ? C22 C23 1.390(10) . ? C23 C24 1.388(8) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.377(7) . ? C25 C30 1.397(7) . ? C25 C31 1.485(7) . ? C26 F5 1.341(7) . ? C26 C27 1.392(9) . ? C27 C28 1.348(10) . ? C27 H27 0.9300 . ? C28 F6 1.340(8) . ? C28 C29 1.351(9) . ? C29 C30 1.387(8) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C36 1.404(7) . ? C31 C32 1.409(7) . ? C32 C33 1.372(7) . ? C32 H32 0.9300 . ? C33 C34 1.386(6) . ? C33 H33 0.9300 . ? C34 C35 1.390(6) . ? C34 C37 1.465(7) . ? C35 C36 1.402(6) . ? C35 C49 1.524(6) . ? C36 H36 0.9300 . ? C37 C38 1.383(6) . ? C37 C42 1.399(6) . ? C38 C39 1.399(7) . ? C38 H38 0.9300 . ? C39 C40 1.382(7) . ? C39 H39 0.9300 . ? C40 C41 1.398(6) . ? C40 C43 1.474(7) . ? C41 C42 1.383(6) . ? C41 H41 0.9300 . ? C42 C49 1.541(6) . ? C43 C44 1.389(7) . ? C43 C48 1.413(7) . ? C44 F7 1.276(7) . ? C44 C45 1.360(8) . ? C45 C46 1.362(9) . ? C45 H45 0.9300 . ? C46 C47 1.353(9) . ? C46 F8 1.372(7) . ? C47 C48 1.395(8) . ? C47 H47 0.9300 . ? F7' C48 1.227(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 116.5(6) . . ? C2 C1 C7 124.0(5) . . ? C6 C1 C7 119.4(5) . . ? F1 C2 C3 117.1(6) . . ? F1 C2 C1 118.4(6) . . ? C3 C2 C1 124.6(6) . . ? C2 C3 C4 117.0(7) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? C5 C4 F2 118.9(7) . . ? C5 C4 C3 122.7(7) . . ? F2 C4 C3 118.3(7) . . ? C4 C5 C6 119.8(7) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 119.4(7) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C8 C7 C12 119.5(5) . . ? C8 C7 C1 119.3(5) . . ? C12 C7 C1 121.2(5) . . ? C9 C8 C7 121.8(5) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C10 118.8(5) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C11 119.5(5) . . ? C9 C10 C13 132.2(5) . . ? C11 C10 C13 108.3(4) . . ? C12 C11 C10 120.9(4) . . ? C12 C11 C49 129.2(4) . . ? C10 C11 C49 109.8(4) . . ? C11 C12 C7 119.5(5) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C18 C13 C14 120.6(5) . . ? C18 C13 C10 110.2(4) . . ? C14 C13 C10 129.2(5) . . ? C13 C14 C15 118.1(5) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 122.3(5) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C15 C16 C17 118.5(5) . . ? C15 C16 C19 118.9(5) . . ? C17 C16 C19 122.6(5) . . ? C18 C17 C16 119.8(5) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C13 120.6(4) . . ? C17 C18 C49 129.7(4) . . ? C13 C18 C49 109.6(4) . . ? C20 C19 C24 117.0(6) . . ? C20 C19 C16 122.3(5) . . ? C24 C19 C16 120.4(5) . . ? C19 C20 F3 119.5(6) . . ? C19 C20 C21 124.3(7) . . ? F3 C20 C21 116.1(7) . . ? C22 C21 C20 116.5(7) . . ? C22 C21 H21 121.7 . . ? C20 C21 H21 121.7 . . ? C21 C22 F4 118.0(8) . . ? C21 C22 C23 122.8(7) . . ? F4 C22 C23 119.2(9) . . ? C24 C23 C22 117.6(7) . . ? C24 C23 H23 121.2 . . ? C22 C23 H23 121.2 . . ? C23 C24 C19 121.7(6) . . ? C23 C24 H24 119.1 . . ? C19 C24 H24 119.1 . . ? C26 C25 C30 116.4(5) . . ? C26 C25 C31 121.5(5) . . ? C30 C25 C31 122.0(5) . . ? F5 C26 C25 119.2(6) . . ? F5 C26 C27 117.8(6) . . ? C25 C26 C27 123.0(7) . . ? C28 C27 C26 118.2(7) . . ? C28 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? F6 C28 C27 117.8(7) . . ? F6 C28 C29 120.7(8) . . ? C27 C28 C29 121.5(7) . . ? C28 C29 C30 120.4(7) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C29 C30 C25 120.5(6) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? C36 C31 C32 118.6(5) . . ? C36 C31 C25 122.0(5) . . ? C32 C31 C25 119.4(5) . . ? C33 C32 C31 122.1(5) . . ? C33 C32 H32 118.9 . . ? C31 C32 H32 118.9 . . ? C32 C33 C34 118.9(5) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C33 C34 C35 120.8(5) . . ? C33 C34 C37 129.8(5) . . ? C35 C34 C37 109.3(4) . . ? C34 C35 C36 120.5(5) . . ? C34 C35 C49 110.8(4) . . ? C36 C35 C49 128.7(4) . . ? C35 C36 C31 119.0(5) . . ? C35 C36 H36 120.5 . . ? C31 C36 H36 120.5 . . ? C38 C37 C42 120.4(4) . . ? C38 C37 C34 131.3(5) . . ? C42 C37 C34 108.3(4) . . ? C37 C38 C39 117.6(5) . . ? C37 C38 H38 121.2 . . ? C39 C38 H38 121.2 . . ? C40 C39 C38 122.7(5) . . ? C40 C39 H39 118.6 . . ? C38 C39 H39 118.6 . . ? C39 C40 C41 118.7(4) . . ? C39 C40 C43 120.3(4) . . ? C41 C40 C43 120.9(4) . . ? C42 C41 C40 119.3(5) . . ? C42 C41 H41 120.3 . . ? C40 C41 H41 120.3 . . ? C41 C42 C37 121.0(4) . . ? C41 C42 C49 128.3(4) . . ? C37 C42 C49 110.5(4) . . ? C44 C43 C48 116.3(5) . . ? C44 C43 C40 122.4(5) . . ? C48 C43 C40 121.3(5) . . ? F7 C44 C45 116.5(6) . . ? F7 C44 C43 120.4(6) . . ? C45 C44 C43 123.1(6) . . ? C44 C45 C46 117.6(6) . . ? C44 C45 H45 121.2 . . ? C46 C45 H45 121.2 . . ? C47 C46 C45 124.3(6) . . ? C47 C46 F8 117.5(7) . . ? C45 C46 F8 118.2(7) . . ? C46 C47 C48 117.3(6) . . ? C46 C47 H47 121.3 . . ? C48 C47 H47 121.3 . . ? C35 C49 C11 113.9(4) . . ? C35 C49 C18 118.2(4) . . ? C11 C49 C18 102.0(4) . . ? C35 C49 C42 101.0(4) . . ? C11 C49 C42 110.2(3) . . ? C18 C49 C42 111.7(4) . . ? F7' C48 C47 117.7(7) . . ? F7' C48 C43 121.0(6) . . ? C47 C48 C43 121.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 176.9(6) . . . . ? C7 C1 C2 F1 -5.1(10) . . . . ? C6 C1 C2 C3 -3.0(11) . . . . ? C7 C1 C2 C3 175.0(7) . . . . ? F1 C2 C3 C4 -178.8(8) . . . . ? C1 C2 C3 C4 1.1(13) . . . . ? C2 C3 C4 C5 0.4(14) . . . . ? C2 C3 C4 F2 -178.9(7) . . . . ? F2 C4 C5 C6 179.6(7) . . . . ? C3 C4 C5 C6 0.3(14) . . . . ? C4 C5 C6 C1 -2.4(11) . . . . ? C2 C1 C6 C5 3.6(9) . . . . ? C7 C1 C6 C5 -174.6(6) . . . . ? C2 C1 C7 C8 -134.0(6) . . . . ? C6 C1 C7 C8 44.0(8) . . . . ? C2 C1 C7 C12 47.5(8) . . . . ? C6 C1 C7 C12 -134.5(6) . . . . ? C12 C7 C8 C9 -2.5(8) . . . . ? C1 C7 C8 C9 178.9(5) . . . . ? C7 C8 C9 C10 1.1(8) . . . . ? C8 C9 C10 C11 1.7(7) . . . . ? C8 C9 C10 C13 -175.8(5) . . . . ? C9 C10 C11 C12 -3.0(7) . . . . ? C13 C10 C11 C12 175.0(4) . . . . ? C9 C10 C11 C49 -179.4(4) . . . . ? C13 C10 C11 C49 -1.3(5) . . . . ? C10 C11 C12 C7 1.6(7) . . . . ? C49 C11 C12 C7 177.1(4) . . . . ? C8 C7 C12 C11 1.2(7) . . . . ? C1 C7 C12 C11 179.7(5) . . . . ? C9 C10 C13 C18 -179.7(5) . . . . ? C11 C10 C13 C18 2.6(5) . . . . ? C9 C10 C13 C14 2.9(9) . . . . ? C11 C10 C13 C14 -174.8(5) . . . . ? C18 C13 C14 C15 1.4(7) . . . . ? C10 C13 C14 C15 178.5(5) . . . . ? C13 C14 C15 C16 0.3(8) . . . . ? C14 C15 C16 C17 -0.4(8) . . . . ? C14 C15 C16 C19 179.7(5) . . . . ? C15 C16 C17 C18 -1.2(7) . . . . ? C19 C16 C17 C18 178.6(5) . . . . ? C16 C17 C18 C13 3.0(7) . . . . ? C16 C17 C18 C49 -174.5(5) . . . . ? C14 C13 C18 C17 -3.1(7) . . . . ? C10 C13 C18 C17 179.3(4) . . . . ? C14 C13 C18 C49 174.9(4) . . . . ? C10 C13 C18 C49 -2.8(5) . . . . ? C15 C16 C19 C20 -45.8(8) . . . . ? C17 C16 C19 C20 134.3(6) . . . . ? C15 C16 C19 C24 128.3(6) . . . . ? C17 C16 C19 C24 -51.6(7) . . . . ? C24 C19 C20 F3 178.1(6) . . . . ? C16 C19 C20 F3 -7.6(9) . . . . ? C24 C19 C20 C21 -0.1(10) . . . . ? C16 C19 C20 C21 174.2(6) . . . . ? C19 C20 C21 C22 0.0(12) . . . . ? F3 C20 C21 C22 -178.3(7) . . . . ? C20 C21 C22 F4 180.0(7) . . . . ? C20 C21 C22 C23 0.4(13) . . . . ? C21 C22 C23 C24 -0.8(12) . . . . ? F4 C22 C23 C24 179.7(7) . . . . ? C22 C23 C24 C19 0.7(10) . . . . ? C20 C19 C24 C23 -0.2(9) . . . . ? C16 C19 C24 C23 -174.6(6) . . . . ? C30 C25 C26 F5 177.9(5) . . . . ? C31 C25 C26 F5 -5.0(8) . . . . ? C30 C25 C26 C27 -2.6(9) . . . . ? C31 C25 C26 C27 174.5(6) . . . . ? F5 C26 C27 C28 -177.7(7) . . . . ? C25 C26 C27 C28 2.7(11) . . . . ? C26 C27 C28 F6 179.5(6) . . . . ? C26 C27 C28 C29 -0.8(12) . . . . ? F6 C28 C29 C30 178.5(6) . . . . ? C27 C28 C29 C30 -1.1(11) . . . . ? C28 C29 C30 C25 1.2(9) . . . . ? C26 C25 C30 C29 0.6(8) . . . . ? C31 C25 C30 C29 -176.5(5) . . . . ? C26 C25 C31 C36 134.8(6) . . . . ? C30 C25 C31 C36 -48.3(7) . . . . ? C26 C25 C31 C32 -46.8(7) . . . . ? C30 C25 C31 C32 130.1(5) . . . . ? C36 C31 C32 C33 -1.8(7) . . . . ? C25 C31 C32 C33 179.7(5) . . . . ? C31 C32 C33 C34 0.8(7) . . . . ? C32 C33 C34 C35 2.3(7) . . . . ? C32 C33 C34 C37 177.5(5) . . . . ? C33 C34 C35 C36 -4.3(7) . . . . ? C37 C34 C35 C36 179.5(4) . . . . ? C33 C34 C35 C49 173.7(4) . . . . ? C37 C34 C35 C49 -2.5(5) . . . . ? C34 C35 C36 C31 3.2(7) . . . . ? C49 C35 C36 C31 -174.4(4) . . . . ? C32 C31 C36 C35 -0.2(7) . . . . ? C25 C31 C36 C35 178.2(4) . . . . ? C33 C34 C37 C38 4.4(9) . . . . ? C35 C34 C37 C38 -179.9(5) . . . . ? C33 C34 C37 C42 -172.7(5) . . . . ? C35 C34 C37 C42 3.0(5) . . . . ? C42 C37 C38 C39 2.9(7) . . . . ? C34 C37 C38 C39 -173.9(5) . . . . ? C37 C38 C39 C40 1.1(8) . . . . ? C38 C39 C40 C41 -2.9(8) . . . . ? C38 C39 C40 C43 175.6(5) . . . . ? C39 C40 C41 C42 0.7(7) . . . . ? C43 C40 C41 C42 -177.8(4) . . . . ? C40 C41 C42 C37 3.2(7) . . . . ? C40 C41 C42 C49 176.8(4) . . . . ? C38 C37 C42 C41 -5.1(7) . . . . ? C34 C37 C42 C41 172.4(4) . . . . ? C38 C37 C42 C49 -179.7(4) . . . . ? C34 C37 C42 C49 -2.3(5) . . . . ? C39 C40 C43 C44 44.8(7) . . . . ? C41 C40 C43 C44 -136.7(5) . . . . ? C39 C40 C43 C48 -132.4(6) . . . . ? C41 C40 C43 C48 46.1(7) . . . . ? C48 C43 C44 F7 -176.7(6) . . . . ? C40 C43 C44 F7 6.0(9) . . . . ? C48 C43 C44 C45 1.9(9) . . . . ? C40 C43 C44 C45 -175.5(6) . . . . ? F7 C44 C45 C46 176.6(6) . . . . ? C43 C44 C45 C46 -1.9(10) . . . . ? C44 C45 C46 C47 1.2(11) . . . . ? C44 C45 C46 F8 -179.5(6) . . . . ? C45 C46 C47 C48 -0.5(11) . . . . ? F8 C46 C47 C48 -179.8(6) . . . . ? C34 C35 C49 C11 -117.0(4) . . . . ? C36 C35 C49 C11 60.8(6) . . . . ? C34 C35 C49 C18 123.2(4) . . . . ? C36 C35 C49 C18 -59.0(6) . . . . ? C34 C35 C49 C42 1.1(5) . . . . ? C36 C35 C49 C42 178.8(4) . . . . ? C12 C11 C49 C35 55.3(6) . . . . ? C10 C11 C49 C35 -128.8(4) . . . . ? C12 C11 C49 C18 -176.2(5) . . . . ? C10 C11 C49 C18 -0.2(5) . . . . ? C12 C11 C49 C42 -57.4(6) . . . . ? C10 C11 C49 C42 118.5(4) . . . . ? C17 C18 C49 C35 -54.7(7) . . . . ? C13 C18 C49 C35 127.6(4) . . . . ? C17 C18 C49 C11 179.5(5) . . . . ? C13 C18 C49 C11 1.8(5) . . . . ? C17 C18 C49 C42 61.9(6) . . . . ? C13 C18 C49 C42 -115.9(4) . . . . ? C41 C42 C49 C35 -173.4(5) . . . . ? C37 C42 C49 C35 0.8(5) . . . . ? C41 C42 C49 C11 -52.6(6) . . . . ? C37 C42 C49 C11 121.5(4) . . . . ? C41 C42 C49 C18 60.0(6) . . . . ? C37 C42 C49 C18 -125.8(4) . . . . ? C46 C47 C48 F7' 178.2(8) . . . . ? C46 C47 C48 C43 0.4(10) . . . . ? C44 C43 C48 F7' -178.7(8) . . . . ? C40 C43 C48 F7' -1.4(10) . . . . ? C44 C43 C48 C47 -1.1(8) . . . . ? C40 C43 C48 C47 176.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.890 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.072