# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Troyanov, Sergey' _publ_contact_author_email stroyano@thermo.chem.msu.ru _publ_section_title ; Regioselective near-equatorial chlorination of Cs-C70(CF3)8 ; loop_ _publ_author_name S.Troyanov A.Goryunkov V.Markov P.Khavrel L.Sidorov N.Belov ; N.Samokhvalova ; # Attachment '- 70CL1A.CIF' data_70cl1a _database_code_depnum_ccdc_archive 'CCDC 768967' #TrackingRef '- 70CL1A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C90 H8 Cl6 F24' _chemical_formula_weight 1757.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y-1/2, z' _cell_length_a 11.4051(3) _cell_length_b 19.1550(5) _cell_length_c 26.9140(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5879.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 30000 _cell_measurement_theta_min 5 _cell_measurement_theta_max 32 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.005 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.986 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3464 _exptl_absorpt_coefficient_mu 0.432 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.90500 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'BL14.2, PSF, BESSY, Berlin, Germany' _diffrn_radiation_monochromator Cu(113) _diffrn_measurement_device_type MAR225 _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54233 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 37.08 _reflns_number_total 6222 _reflns_number_gt 6089 _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^)+(0.0100P)^2^+40.0000P] 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 6222 _refine_ls_number_parameters 548 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.2132 _refine_ls_wR_factor_gt 0.2129 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.31965(11) 0.13110(5) 0.69421(5) 0.0317(3) Uani 1 1 d . . . Cl2 Cl 0.66906(13) 0.17618(7) 0.41069(6) 0.0450(4) Uani 1 1 d . . . Cl3 Cl 0.6337(2) 0.15703(12) 0.52495(7) 0.0741(6) Uani 1 1 d . . . F1 F 0.1275(3) 0.36100(17) 0.52758(11) 0.0384(7) Uani 1 1 d . . . F2 F -0.0517(3) 0.33734(17) 0.54624(11) 0.0413(7) Uani 1 1 d . . . F3 F 0.0028(3) 0.44338(16) 0.53601(11) 0.0436(8) Uani 1 1 d . . . F4 F 0.3821(3) 0.21248(15) 0.59233(11) 0.0397(7) Uani 1 1 d . . . F5 F 0.2255(3) 0.24664(16) 0.55640(12) 0.0397(7) Uani 1 1 d . . . F6 F 0.3829(3) 0.30740(15) 0.54947(11) 0.0386(7) Uani 1 1 d . . . F7 F -0.0102(3) 0.65341(14) 0.62115(11) 0.0369(7) Uani 1 1 d . . . F8 F 0.1162(3) 0.60571(16) 0.57227(11) 0.0375(7) Uani 1 1 d . . . F9 F -0.0601(3) 0.56791(14) 0.57484(11) 0.0361(7) Uani 1 1 d . . . F10 F 0.3287(3) 0.71078(14) 0.70264(11) 0.0337(7) Uani 1 1 d . . . F11 F 0.4081(3) 0.65659(14) 0.64112(11) 0.0327(6) Uani 1 1 d . . . F12 F 0.2245(3) 0.68288(14) 0.63956(11) 0.0336(6) Uani 1 1 d . . . C1 C 0.0629(4) 0.3886(2) 0.60971(16) 0.0230(9) Uani 1 1 d . . . C2 C 0.1761(4) 0.4297(2) 0.61835(16) 0.0233(9) Uani 1 1 d . . . C3 C 0.2793(4) 0.3917(2) 0.62110(16) 0.0236(9) Uani 1 1 d . . . C4 C 0.2885(4) 0.3108(2) 0.62851(17) 0.0236(9) Uani 1 1 d . . . C5 C 0.1754(4) 0.2850(2) 0.65206(17) 0.0237(9) Uani 1 1 d . . . C6 C 0.0716(4) 0.3170(2) 0.63757(17) 0.0237(9) Uani 1 1 d . . . C7 C -0.0330(4) 0.3068(2) 0.66510(17) 0.0227(8) Uani 1 1 d . . . C8 C -0.1018(4) 0.3697(2) 0.66493(17) 0.0235(9) Uani 1 1 d . . . C9 C -0.0399(4) 0.4213(2) 0.63721(16) 0.0231(9) Uani 1 1 d . . . C10 C -0.0412(4) 0.4891(2) 0.65374(16) 0.0226(8) Uani 1 1 d . . . C11 C 0.0597(4) 0.5405(2) 0.64491(16) 0.0233(9) Uani 1 1 d . . . C12 C 0.1741(4) 0.5013(2) 0.63527(16) 0.0227(8) Uani 1 1 d . . . C13 C 0.2765(4) 0.5309(2) 0.65396(16) 0.0237(9) Uani 1 1 d . . . C14 C 0.3811(4) 0.4918(2) 0.65615(17) 0.0235(9) Uani 1 1 d . . . C15 C 0.3831(4) 0.4225(2) 0.63995(17) 0.0238(9) Uani 1 1 d . . . C16 C 0.4518(4) 0.3717(2) 0.66591(17) 0.0242(9) Uani 1 1 d . . . C17 C 0.3905(4) 0.3074(2) 0.66527(17) 0.0238(9) Uani 1 1 d . . . C18 C 0.3899(4) 0.2656(2) 0.70672(17) 0.0240(9) Uani 1 1 d . . . C19 C 0.2900(4) 0.2180(2) 0.71980(18) 0.0268(9) Uani 1 1 d . . . C20 C 0.1770(4) 0.2418(2) 0.69543(17) 0.0237(9) Uani 1 1 d . . . C21 C 0.0749(4) 0.2334(2) 0.72292(17) 0.0224(9) Uani 1 1 d . . . C22 C -0.0323(4) 0.2642(2) 0.70679(16) 0.0226(9) Uani 1 1 d . . . C23 C -0.1003(5) 0.2826(3) 0.7500 0.0224(12) Uani 1 2 d S . . C24 C -0.1680(5) 0.3426(3) 0.7500 0.0235(12) Uani 1 2 d S . . C25 C -0.1701(4) 0.3870(2) 0.70640(17) 0.0234(9) Uani 1 1 d . . . C26 C -0.1711(4) 0.4581(2) 0.72338(17) 0.0229(9) Uani 1 1 d . . . C27 C -0.1039(4) 0.5072(2) 0.69701(16) 0.0214(8) Uani 1 1 d . . . C28 C -0.0356(4) 0.5579(2) 0.72396(17) 0.0221(8) Uani 1 1 d . . . C29 C 0.0671(4) 0.5744(2) 0.69770(16) 0.0216(8) Uani 1 1 d . . . C30 C 0.1695(4) 0.5916(2) 0.72320(17) 0.0222(8) Uani 1 1 d . . . C31 C 0.2831(4) 0.5899(2) 0.69312(16) 0.0225(8) Uani 1 1 d . . . C32 C 0.3862(4) 0.5654(2) 0.72458(17) 0.0227(9) Uani 1 1 d . . . C33 C 0.4503(4) 0.5131(2) 0.69820(17) 0.0230(8) Uani 1 1 d . . . C34 C 0.5186(4) 0.4637(2) 0.72333(17) 0.0240(9) Uani 1 1 d . . . C35 C 0.5193(4) 0.3915(2) 0.70656(17) 0.0234(9) Uani 1 1 d . . . C36 C 0.5201(5) 0.3475(3) 0.7500 0.0259(13) Uani 1 2 d S . . C37 C 0.4530(6) 0.2870(3) 0.7500 0.0234(12) Uani 1 2 d S . . C38 C 0.0355(4) 0.3826(2) 0.55408(18) 0.0282(9) Uani 1 1 d . . . C39 C 0.3192(4) 0.2690(2) 0.58108(18) 0.0281(9) Uani 1 1 d . . . C40 C 0.0269(4) 0.5923(2) 0.60296(16) 0.0229(8) Uani 1 1 d . . . C41 C 0.3108(4) 0.6611(2) 0.66882(17) 0.0229(8) Uani 1 1 d . . . C42 C 0.6622(5) 0.0926(3) 0.4363(2) 0.0417(12) Uani 1 1 d . . . C43 C 0.6492(6) 0.0842(4) 0.4870(2) 0.0547(16) Uani 1 1 d . . . C44 C 0.6475(7) 0.0185(5) 0.5075(3) 0.066(2) Uani 1 1 d . . . H44 H 0.6405 0.0136 0.5425 0.079 Uiso 1 1 calc R . . C45 C 0.6557(6) -0.0395(4) 0.4786(4) 0.067(2) Uani 1 1 d . . . H45 H 0.6545 -0.0847 0.4932 0.080 Uiso 1 1 calc R . . C46 C 0.6664(6) -0.0312(4) 0.4255(3) 0.0541(16) Uani 1 1 d . . . H46 H 0.6707 -0.0713 0.4048 0.065 Uiso 1 1 calc R . . C47 C 0.6703(6) 0.0343(5) 0.4046(3) 0.0428(15) Uani 1 1 d . . . H47 H 0.6783 0.0400 0.3697 0.051 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0346(6) 0.0147(5) 0.0460(7) -0.0029(4) 0.0012(5) 0.0027(4) Cl2 0.0463(8) 0.0349(7) 0.0537(8) -0.0035(6) -0.0011(6) 0.0003(6) Cl3 0.0871(14) 0.0857(14) 0.0496(10) -0.0204(9) -0.0101(9) 0.0266(11) F1 0.0412(17) 0.0438(17) 0.0302(15) -0.0062(12) 0.0029(12) 0.0075(14) F2 0.0437(17) 0.0449(17) 0.0353(16) -0.0071(13) -0.0039(13) -0.0170(15) F3 0.071(2) 0.0280(14) 0.0314(15) 0.0015(12) -0.0067(15) 0.0150(15) F4 0.0564(19) 0.0252(14) 0.0375(16) -0.0055(12) -0.0005(14) 0.0172(14) F5 0.0376(16) 0.0392(16) 0.0424(17) -0.0160(13) -0.0017(13) -0.0009(14) F6 0.0504(18) 0.0273(14) 0.0380(16) -0.0034(12) 0.0159(14) -0.0058(13) F7 0.0572(19) 0.0191(12) 0.0343(15) -0.0006(11) -0.0027(14) 0.0144(13) F8 0.0371(16) 0.0365(15) 0.0389(16) 0.0142(13) 0.0065(13) 0.0025(13) F9 0.0460(17) 0.0255(13) 0.0369(15) 0.0053(11) -0.0135(13) -0.0084(13) F10 0.0496(18) 0.0163(12) 0.0353(15) -0.0019(10) 0.0021(13) -0.0097(12) F11 0.0315(14) 0.0241(13) 0.0426(16) 0.0054(11) 0.0119(12) -0.0020(11) F12 0.0344(15) 0.0233(13) 0.0431(16) 0.0113(11) -0.0056(12) -0.0015(12) C1 0.028(2) 0.0150(18) 0.026(2) 0.0000(15) -0.0012(17) -0.0014(17) C2 0.030(2) 0.0155(18) 0.025(2) -0.0022(15) 0.0000(17) -0.0007(17) C3 0.029(2) 0.0151(18) 0.027(2) -0.0005(15) -0.0001(17) -0.0005(17) C4 0.026(2) 0.0139(18) 0.031(2) -0.0001(15) 0.0024(17) 0.0017(16) C5 0.027(2) 0.0129(17) 0.031(2) -0.0051(15) -0.0005(17) 0.0000(16) C6 0.029(2) 0.0091(16) 0.033(2) -0.0033(15) -0.0016(17) -0.0013(16) C7 0.026(2) 0.0114(17) 0.030(2) -0.0024(15) -0.0016(17) -0.0024(16) C8 0.023(2) 0.0163(18) 0.031(2) -0.0024(16) -0.0019(17) -0.0023(17) C9 0.027(2) 0.0147(18) 0.028(2) -0.0002(15) -0.0032(17) 0.0001(16) C10 0.023(2) 0.0162(18) 0.028(2) -0.0014(16) -0.0023(16) -0.0002(16) C11 0.028(2) 0.0130(17) 0.029(2) 0.0000(15) 0.0007(17) 0.0002(17) C12 0.026(2) 0.0143(18) 0.027(2) 0.0003(15) 0.0015(17) -0.0010(16) C13 0.030(2) 0.0119(17) 0.029(2) 0.0009(15) 0.0007(17) -0.0021(17) C14 0.024(2) 0.0163(18) 0.031(2) 0.0010(16) 0.0038(17) -0.0023(16) C15 0.025(2) 0.0163(19) 0.030(2) -0.0004(16) 0.0049(17) -0.0016(17) C16 0.024(2) 0.0173(18) 0.031(2) -0.0018(16) 0.0042(17) 0.0026(17) C17 0.025(2) 0.0157(18) 0.031(2) -0.0028(16) 0.0032(17) 0.0040(17) C18 0.024(2) 0.0142(18) 0.034(2) -0.0016(16) 0.0015(17) 0.0037(16) C19 0.029(2) 0.0133(18) 0.038(3) 0.0002(16) -0.0022(19) 0.0027(17) C20 0.023(2) 0.0104(17) 0.037(2) -0.0032(16) -0.0020(17) 0.0005(16) C21 0.022(2) 0.0086(17) 0.037(2) -0.0015(15) 0.0013(17) -0.0013(15) C22 0.023(2) 0.0124(17) 0.032(2) -0.0026(15) -0.0016(17) -0.0011(16) C23 0.024(3) 0.013(2) 0.031(3) 0.000 0.000 -0.004(2) C24 0.018(3) 0.015(3) 0.037(3) 0.000 0.000 -0.005(2) C25 0.020(2) 0.0153(18) 0.034(2) -0.0029(16) -0.0005(17) 0.0009(16) C26 0.0177(19) 0.0122(18) 0.039(2) 0.0003(16) -0.0042(17) 0.0030(15) C27 0.022(2) 0.0139(17) 0.028(2) 0.0020(15) -0.0007(16) 0.0032(16) C28 0.023(2) 0.0095(16) 0.034(2) -0.0002(15) -0.0004(17) 0.0025(16) C29 0.023(2) 0.0099(16) 0.032(2) 0.0004(15) -0.0024(16) -0.0013(15) C30 0.022(2) 0.0111(17) 0.033(2) 0.0008(15) -0.0003(17) 0.0004(16) C31 0.024(2) 0.0133(17) 0.030(2) 0.0010(15) 0.0018(17) -0.0013(16) C32 0.022(2) 0.0105(17) 0.036(2) 0.0017(16) 0.0005(17) -0.0030(16) C33 0.0208(19) 0.0185(19) 0.030(2) -0.0005(16) 0.0015(16) -0.0033(16) C34 0.021(2) 0.0148(18) 0.036(2) 0.0002(16) 0.0031(17) -0.0038(16) C35 0.020(2) 0.0182(19) 0.032(2) -0.0002(16) 0.0020(16) -0.0020(16) C36 0.020(3) 0.019(3) 0.038(3) 0.000 0.000 0.005(2) C37 0.024(3) 0.015(3) 0.032(3) 0.000 0.000 0.006(2) C38 0.030(2) 0.019(2) 0.035(2) -0.0050(17) 0.0007(18) 0.0018(18) C39 0.031(2) 0.0178(19) 0.036(2) -0.0021(17) 0.0008(19) -0.0011(18) C40 0.024(2) 0.0152(18) 0.029(2) -0.0015(15) 0.0010(16) -0.0010(16) C41 0.0216(19) 0.0175(18) 0.030(2) 0.0004(16) 0.0025(16) 0.0022(16) C42 0.035(3) 0.049(3) 0.042(3) 0.002(2) -0.003(2) 0.002(2) C43 0.045(3) 0.074(5) 0.046(3) 0.001(3) -0.001(3) 0.010(3) C44 0.063(4) 0.090(6) 0.045(4) 0.014(4) 0.003(3) 0.011(4) C45 0.047(4) 0.040(3) 0.113(7) 0.026(4) 0.006(4) 0.010(3) C46 0.052(4) 0.040(3) 0.071(5) -0.001(3) 0.001(3) 0.006(3) C47 0.033(3) 0.037(4) 0.058(4) 0.007(3) 0.000(3) 0.003(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 Cl1 C19 1.832(4) . ? Cl2 C42 1.745(6) . ? Cl3 C43 1.737(8) . ? F1 C38 1.334(6) . ? F2 C38 1.335(6) . ? F3 C38 1.316(5) . ? F4 C39 1.334(5) . ? F5 C39 1.329(6) . ? F6 C39 1.340(6) . ? F7 C40 1.337(5) . ? F8 C40 1.336(5) . ? F9 C40 1.333(5) . ? F10 C41 1.333(5) . ? F11 C41 1.340(5) . ? F12 C41 1.327(5) . ? C1 C9 1.522(6) . ? C1 C2 1.529(6) . ? C1 C38 1.534(6) . ? C1 C6 1.565(6) . ? C2 C3 1.386(6) . ? C2 C12 1.447(6) . ? C3 C15 1.416(6) . ? C3 C4 1.565(6) . ? C4 C5 1.520(6) . ? C4 C17 1.528(6) . ? C4 C39 1.547(6) . ? C5 C6 1.390(6) . ? C5 C20 1.431(6) . ? C6 C7 1.418(6) . ? C7 C22 1.387(6) . ? C7 C8 1.438(6) . ? C8 C25 1.401(6) . ? C8 C9 1.426(6) . ? C9 C10 1.373(6) . ? C10 C27 1.410(6) . ? C10 C11 1.533(6) . ? C11 C12 1.527(6) . ? C11 C40 1.550(6) . ? C11 C29 1.564(6) . ? C12 C13 1.391(6) . ? C13 C14 1.410(6) . ? C13 C31 1.547(6) . ? C14 C15 1.397(6) . ? C14 C33 1.439(6) . ? C15 C16 1.432(6) . ? C16 C35 1.391(6) . ? C16 C17 1.417(6) . ? C17 C18 1.372(6) . ? C18 C37 1.429(6) . ? C18 C19 1.502(6) . ? C19 C20 1.516(6) . ? C19 C19 1.626(10) 6_557 ? C20 C21 1.390(6) . ? C21 C22 1.425(6) . ? C21 C21 1.457(9) 6_557 ? C22 C23 1.442(6) . ? C23 C24 1.385(9) . ? C23 C22 1.442(6) 6_557 ? C24 C25 1.449(6) 6_557 ? C24 C25 1.449(6) . ? C25 C26 1.438(6) . ? C26 C27 1.405(6) . ? C26 C26 1.433(9) 6_557 ? C27 C28 1.442(6) . ? C28 C28 1.402(9) 6_557 ? C28 C29 1.404(6) . ? C29 C30 1.394(6) . ? C30 C30 1.443(9) 6_557 ? C30 C31 1.528(6) . ? C31 C32 1.523(6) . ? C31 C41 1.545(6) . ? C32 C32 1.368(9) 6_557 ? C32 C33 1.429(6) . ? C33 C34 1.400(6) . ? C34 C34 1.436(9) 6_557 ? C34 C35 1.453(6) . ? C35 C36 1.442(6) . ? C36 C37 1.388(9) . ? C36 C35 1.442(6) 6_557 ? C37 C18 1.429(6) 6_557 ? C42 C43 1.383(9) . ? C42 C47 1.408(12) . ? C43 C44 1.374(12) . ? C44 C45 1.359(12) . ? C45 C46 1.444(12) . ? C46 C47 1.375(10) . ? 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 C9 C1 C2 111.4(3) . . ? C9 C1 C38 110.4(4) . . ? C2 C1 C38 111.0(4) . . ? C9 C1 C6 100.1(3) . . ? C2 C1 C6 108.9(3) . . ? C38 C1 C6 114.5(3) . . ? C3 C2 C12 119.6(4) . . ? C3 C2 C1 117.1(4) . . ? C12 C2 C1 121.5(4) . . ? C2 C3 C15 120.7(4) . . ? C2 C3 C4 125.6(4) . . ? C15 C3 C4 108.1(4) . . ? C5 C4 C17 111.2(4) . . ? C5 C4 C39 111.5(4) . . ? C17 C4 C39 109.9(4) . . ? C5 C4 C3 108.6(3) . . ? C17 C4 C3 100.2(3) . . ? C39 C4 C3 115.0(4) . . ? C6 C5 C20 119.7(4) . . ? C6 C5 C4 117.5(4) . . ? C20 C5 C4 121.2(4) . . ? C5 C6 C7 120.6(4) . . ? C5 C6 C1 125.1(4) . . ? C7 C6 C1 108.6(4) . . ? C22 C7 C6 120.0(4) . . ? C22 C7 C8 119.9(4) . . ? C6 C7 C8 109.9(4) . . ? C25 C8 C9 121.9(4) . . ? C25 C8 C7 119.9(4) . . ? C9 C8 C7 108.2(4) . . ? C10 C9 C8 118.8(4) . . ? C10 C9 C1 123.7(4) . . ? C8 C9 C1 110.5(4) . . ? C9 C10 C27 120.4(4) . . ? C9 C10 C11 123.3(4) . . ? C27 C10 C11 110.6(4) . . ? C12 C11 C10 110.7(3) . . ? C12 C11 C40 113.4(4) . . ? C10 C11 C40 110.1(4) . . ? C12 C11 C29 108.2(4) . . ? C10 C11 C29 99.6(3) . . ? C40 C11 C29 114.1(3) . . ? C13 C12 C2 119.1(4) . . ? C13 C12 C11 117.1(4) . . ? C2 C12 C11 122.2(4) . . ? C12 C13 C14 120.6(4) . . ? C12 C13 C31 125.8(4) . . ? C14 C13 C31 108.5(4) . . ? C15 C14 C13 120.3(4) . . ? C15 C14 C33 120.4(4) . . ? C13 C14 C33 110.3(4) . . ? C14 C15 C3 119.6(4) . . ? C14 C15 C16 120.2(4) . . ? C3 C15 C16 110.4(4) . . ? C35 C16 C17 121.4(4) . . ? C35 C16 C15 120.1(4) . . ? C17 C16 C15 108.4(4) . . ? C18 C17 C16 119.9(4) . . ? C18 C17 C4 123.2(4) . . ? C16 C17 C4 110.2(4) . . ? C17 C18 C37 119.6(4) . . ? C17 C18 C19 123.2(4) . . ? C37 C18 C19 111.4(4) . . ? C18 C19 C20 111.1(4) . . ? C18 C19 C19 103.6(3) . 6_557 ? C20 C19 C19 115.6(3) . 6_557 ? C18 C19 Cl1 108.9(3) . . ? C20 C19 Cl1 105.5(3) . . ? C19 C19 Cl1 112.07(15) 6_557 . ? C21 C20 C5 119.4(4) . . ? C21 C20 C19 116.6(4) . . ? C5 C20 C19 122.5(4) . . ? C20 C21 C22 120.6(4) . . ? C20 C21 C21 122.2(3) . 6_557 ? C22 C21 C21 107.7(3) . 6_557 ? C7 C22 C21 119.7(4) . . ? C7 C22 C23 120.4(4) . . ? C21 C22 C23 108.5(4) . . ? C24 C23 C22 120.2(3) . . ? C24 C23 C22 120.2(3) . 6_557 ? C22 C23 C22 107.5(5) . 6_557 ? C23 C24 C25 119.7(3) . 6_557 ? C23 C24 C25 119.7(3) . . ? C25 C24 C25 108.2(5) 6_557 . ? C8 C25 C26 118.8(4) . . ? C8 C25 C24 119.8(4) . . ? C26 C25 C24 107.4(4) . . ? C27 C26 C26 120.3(3) . 6_557 ? C27 C26 C25 118.0(4) . . ? C26 C26 C25 108.5(3) 6_557 . ? C26 C27 C10 122.0(4) . . ? C26 C27 C28 119.4(4) . . ? C10 C27 C28 107.9(4) . . ? C28 C28 C29 120.2(3) 6_557 . ? C28 C28 C27 120.2(2) 6_557 . ? C29 C28 C27 110.4(4) . . ? C30 C29 C28 120.3(4) . . ? C30 C29 C11 126.2(4) . . ? C28 C29 C11 108.6(4) . . ? C29 C30 C30 119.5(3) . 6_557 ? C29 C30 C31 116.4(4) . . ? C30 C30 C31 122.0(2) 6_557 . ? C32 C31 C30 111.5(4) . . ? C32 C31 C41 110.5(3) . . ? C30 C31 C41 112.2(3) . . ? C32 C31 C13 101.1(3) . . ? C30 C31 C13 109.6(3) . . ? C41 C31 C13 111.5(3) . . ? C32 C32 C33 119.8(3) 6_557 . ? C32 C32 C31 123.8(2) 6_557 . ? C33 C32 C31 109.6(4) . . ? C34 C33 C32 121.3(4) . . ? C34 C33 C14 119.6(4) . . ? C32 C33 C14 108.0(4) . . ? C33 C34 C34 118.9(3) . 6_557 ? C33 C34 C35 119.7(4) . . ? C34 C34 C35 108.1(3) 6_557 . ? C16 C35 C36 118.7(4) . . ? C16 C35 C34 120.1(4) . . ? C36 C35 C34 107.7(4) . . ? C37 C36 C35 119.0(3) . . ? C37 C36 C35 119.0(3) . 6_557 ? C35 C36 C35 108.3(5) . 6_557 ? C36 C37 C18 121.1(3) . . ? C36 C37 C18 121.1(3) . 6_557 ? C18 C37 C18 109.2(6) . 6_557 ? F3 C38 F1 107.4(4) . . ? F3 C38 F2 107.7(4) . . ? F1 C38 F2 107.5(4) . . ? F3 C38 C1 110.6(4) . . ? F1 C38 C1 112.6(4) . . ? F2 C38 C1 110.8(4) . . ? F5 C39 F4 106.5(4) . . ? F5 C39 F6 107.2(4) . . ? F4 C39 F6 107.3(4) . . ? F5 C39 C4 113.4(4) . . ? F4 C39 C4 110.8(4) . . ? F6 C39 C4 111.2(4) . . ? F9 C40 F8 106.5(4) . . ? F9 C40 F7 106.2(4) . . ? F8 C40 F7 107.4(3) . . ? F9 C40 C11 111.6(3) . . ? F8 C40 C11 112.9(4) . . ? F7 C40 C11 111.7(4) . . ? F12 C41 F10 107.1(3) . . ? F12 C41 F11 107.7(4) . . ? F10 C41 F11 107.3(4) . . ? F12 C41 C31 112.2(4) . . ? F10 C41 C31 111.9(4) . . ? F11 C41 C31 110.3(3) . . ? C43 C42 C47 120.9(6) . . ? C43 C42 Cl2 120.0(5) . . ? C47 C42 Cl2 119.1(5) . . ? C44 C43 C42 120.2(7) . . ? C44 C43 Cl3 119.9(6) . . ? C42 C43 Cl3 119.9(6) . . ? C45 C44 C43 121.2(7) . . ? C44 C45 C46 118.9(6) . . ? C47 C46 C45 120.4(7) . . ? C46 C47 C42 118.3(7) . . ? _diffrn_measured_fraction_theta_max 0.836 _diffrn_reflns_theta_full 32.60 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.899 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.123