# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_xz121_0m _database_code_depnum_ccdc_archive 'CCDC 893908' #TrackingRef 'all-cifs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H9 B Cl F15' _chemical_formula_weight 724.65 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' B B 0.0013 0.0007 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6340(5) _cell_length_b 33.9056(19) _cell_length_c 11.2130(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.018(3) _cell_angle_gamma 90.00 _cell_volume 2866.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5600 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 19.56 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9627 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 45866 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6577 _reflns_number_gt 3246 _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^)+(0.0728P)^2^+2.3924P] 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 6577 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1563 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1927 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.4471(2) 0.78531(4) 0.13632(16) 0.0978(5) Uani 1 1 d . . . F1 F 0.3760(3) 0.61573(8) 0.5085(2) 0.0706(7) Uani 1 1 d . . . F2 F 0.3459(4) 0.61475(10) 0.7430(2) 0.0954(10) Uani 1 1 d . . . F3 F 0.0276(4) 0.62830(9) 0.8141(2) 0.0911(9) Uani 1 1 d . . . F4 F -0.2567(4) 0.64587(8) 0.6482(2) 0.0773(8) Uani 1 1 d . . . F5 F -0.2266(3) 0.65102(8) 0.4147(2) 0.0664(7) Uani 1 1 d . . . F6 F 0.0902(3) 0.71867(6) 0.3825(2) 0.0675(7) Uani 1 1 d . . . F7 F -0.0434(4) 0.77788(8) 0.2409(3) 0.1053(11) Uani 1 1 d . . . F8 F -0.2142(4) 0.76295(10) 0.0138(3) 0.1130(12) Uani 1 1 d . . . F9 F -0.2509(4) 0.68747(11) -0.0668(2) 0.0974(10) Uani 1 1 d . . . F10 F -0.1067(3) 0.62834(8) 0.0708(2) 0.0690(7) Uani 1 1 d . . . F11 F -0.1277(3) 0.56951(7) 0.2804(2) 0.0626(7) Uani 1 1 d . . . F12 F -0.1614(4) 0.49538(8) 0.3588(2) 0.0820(8) Uani 1 1 d . . . F13 F 0.1284(5) 0.44914(7) 0.4132(3) 0.0960(10) Uani 1 1 d . . . F14 F 0.4532(4) 0.47732(7) 0.3888(2) 0.0848(9) Uani 1 1 d . . . F15 F 0.4892(3) 0.55156(7) 0.3157(2) 0.0650(7) Uani 1 1 d . . . C1 C 0.1976(5) 0.60461(10) 0.2537(3) 0.0387(8) Uani 1 1 d . . . C2 C 0.2923(5) 0.61361(10) 0.1633(3) 0.0418(9) Uani 1 1 d . . . C3 C 0.3375(5) 0.58460(11) 0.0736(3) 0.0471(10) Uani 1 1 d . . . C4 C 0.2109(6) 0.55753(12) 0.0216(4) 0.0586(11) Uani 1 1 d . . . H4A H 0.0986 0.5567 0.0458 0.070 Uiso 1 1 calc R . . C5 C 0.2513(9) 0.53192(15) -0.0657(4) 0.0797(16) Uani 1 1 d . . . H5A H 0.1656 0.5137 -0.1006 0.096 Uiso 1 1 calc R . . C6 C 0.4138(10) 0.53258(18) -0.1022(5) 0.0907(18) Uani 1 1 d . . . H6A H 0.4393 0.5147 -0.1613 0.109 Uiso 1 1 calc R . . C7 C 0.5388(8) 0.55896(17) -0.0534(5) 0.0830(16) Uani 1 1 d . . . H7A H 0.6503 0.5592 -0.0791 0.100 Uiso 1 1 calc R . . C8 C 0.5031(6) 0.58572(14) 0.0348(4) 0.0648(12) Uani 1 1 d . . . H8A H 0.5892 0.6042 0.0675 0.078 Uiso 1 1 calc R . . C9 C 0.0750(5) 0.63378(10) 0.4515(3) 0.0409(9) Uani 1 1 d . . . C10 C 0.2144(5) 0.62346(11) 0.5396(4) 0.0476(10) Uani 1 1 d . . . C11 C 0.2016(6) 0.62263(12) 0.6609(4) 0.0586(12) Uani 1 1 d . . . C12 C 0.0440(7) 0.62994(12) 0.6965(4) 0.0556(11) Uani 1 1 d . . . C13 C -0.1018(6) 0.63930(11) 0.6134(4) 0.0517(10) Uani 1 1 d . . . C14 C -0.0817(5) 0.64142(10) 0.4940(4) 0.0451(9) Uani 1 1 d . . . C15 C -0.0016(5) 0.67092(11) 0.2337(3) 0.0430(9) Uani 1 1 d . . . C16 C 0.0061(5) 0.70984(11) 0.2725(4) 0.0505(10) Uani 1 1 d . . . C17 C -0.0624(6) 0.74079(12) 0.2005(5) 0.0647(13) Uani 1 1 d . . . C18 C -0.1477(6) 0.73350(16) 0.0865(5) 0.0719(15) Uani 1 1 d . . . C19 C -0.1650(5) 0.69545(16) 0.0452(4) 0.0636(13) Uani 1 1 d . . . C20 C -0.0903(5) 0.66516(13) 0.1173(4) 0.0507(10) Uani 1 1 d . . . C21 C 0.1808(5) 0.56296(10) 0.2929(3) 0.0419(9) Uani 1 1 d . . . C22 C 0.0198(5) 0.54718(11) 0.3073(3) 0.0466(10) Uani 1 1 d . . . C23 C -0.0017(6) 0.50910(13) 0.3462(4) 0.0565(11) Uani 1 1 d . . . C24 C 0.1467(8) 0.48597(12) 0.3724(4) 0.0648(13) Uani 1 1 d . . . C25 C 0.3080(6) 0.50018(12) 0.3615(4) 0.0559(11) Uani 1 1 d . . . C26 C 0.3262(6) 0.53829(11) 0.3229(3) 0.0473(10) Uani 1 1 d . . . C27 C 0.3486(5) 0.65499(11) 0.1524(3) 0.0419(9) Uani 1 1 d . . . C28 C 0.4185(5) 0.67596(11) 0.2564(4) 0.0481(10) Uani 1 1 d . . . H28A H 0.4416 0.6628 0.3310 0.058 Uiso 1 1 calc R . . C29 C 0.4537(5) 0.71565(12) 0.2506(4) 0.0549(11) Uani 1 1 d . . . H29A H 0.5026 0.7295 0.3206 0.066 Uiso 1 1 calc R . . C30 C 0.4168(5) 0.73472(12) 0.1422(5) 0.0570(11) Uani 1 1 d . . . C31 C 0.3544(6) 0.71458(13) 0.0373(4) 0.0607(12) Uani 1 1 d . . . H31A H 0.3317 0.7281 -0.0367 0.073 Uiso 1 1 calc R . . C32 C 0.3258(5) 0.67467(12) 0.0417(4) 0.0507(10) Uani 1 1 d . . . H32A H 0.2906 0.6605 -0.0301 0.061 Uiso 1 1 calc R . . B1 B 0.0949(5) 0.63661(12) 0.3137(4) 0.0410(10) 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 Cl1 0.1000(11) 0.0424(7) 0.1517(15) 0.0077(7) 0.0216(10) -0.0114(7) F1 0.0573(16) 0.0861(18) 0.0631(16) 0.0164(13) -0.0075(12) 0.0119(13) F2 0.091(2) 0.125(3) 0.0597(17) 0.0247(16) -0.0237(15) 0.0054(18) F3 0.129(3) 0.098(2) 0.0450(16) 0.0063(14) 0.0112(16) 0.0019(18) F4 0.0791(19) 0.0839(19) 0.0740(18) -0.0012(14) 0.0281(15) 0.0122(15) F5 0.0475(14) 0.0863(18) 0.0622(16) 0.0075(13) -0.0014(12) 0.0123(13) F6 0.0762(17) 0.0426(13) 0.0801(19) -0.0065(12) 0.0007(14) -0.0001(12) F7 0.116(3) 0.0471(17) 0.158(3) 0.0233(18) 0.036(2) 0.0235(16) F8 0.098(2) 0.112(2) 0.133(3) 0.083(2) 0.031(2) 0.0505(19) F9 0.0688(18) 0.157(3) 0.0610(18) 0.0393(18) -0.0067(14) 0.0228(18) F10 0.0654(16) 0.0784(18) 0.0559(15) 0.0009(13) -0.0131(12) -0.0040(13) F11 0.0482(14) 0.0725(16) 0.0652(16) 0.0049(13) 0.0031(11) -0.0104(12) F12 0.091(2) 0.0839(19) 0.0726(18) 0.0033(14) 0.0165(15) -0.0483(16) F13 0.165(3) 0.0353(14) 0.090(2) 0.0122(13) 0.028(2) -0.0171(16) F14 0.120(2) 0.0548(15) 0.0825(19) 0.0185(14) 0.0244(17) 0.0399(16) F15 0.0540(15) 0.0635(15) 0.0780(17) 0.0206(13) 0.0119(12) 0.0133(12) C1 0.038(2) 0.0346(19) 0.041(2) 0.0047(16) -0.0011(16) -0.0042(16) C2 0.038(2) 0.040(2) 0.044(2) 0.0059(17) -0.0033(17) -0.0019(16) C3 0.057(3) 0.044(2) 0.039(2) 0.0097(18) 0.0028(19) 0.009(2) C4 0.081(3) 0.050(2) 0.043(2) 0.001(2) 0.005(2) -0.001(2) C5 0.114(5) 0.070(3) 0.050(3) -0.009(2) -0.005(3) 0.003(3) C6 0.129(6) 0.083(4) 0.063(4) 0.001(3) 0.026(4) 0.034(4) C7 0.103(4) 0.081(4) 0.072(4) 0.016(3) 0.036(3) 0.032(3) C8 0.070(3) 0.064(3) 0.062(3) 0.013(2) 0.017(2) 0.014(2) C9 0.045(2) 0.0292(18) 0.045(2) 0.0015(16) -0.0036(18) 0.0009(16) C10 0.047(2) 0.043(2) 0.051(3) 0.0057(18) 0.0000(19) 0.0048(18) C11 0.067(3) 0.053(3) 0.047(3) 0.013(2) -0.017(2) 0.000(2) C12 0.079(3) 0.046(2) 0.041(3) 0.0049(19) 0.006(2) 0.000(2) C13 0.065(3) 0.037(2) 0.054(3) 0.0014(19) 0.014(2) 0.002(2) C14 0.048(2) 0.037(2) 0.047(2) 0.0022(17) -0.0027(19) 0.0027(18) C15 0.035(2) 0.043(2) 0.048(2) 0.0089(18) -0.0003(17) 0.0027(17) C16 0.043(2) 0.042(2) 0.064(3) 0.006(2) 0.002(2) 0.0011(18) C17 0.054(3) 0.042(3) 0.101(4) 0.016(3) 0.021(3) 0.014(2) C18 0.055(3) 0.077(4) 0.086(4) 0.045(3) 0.018(3) 0.028(3) C19 0.041(2) 0.096(4) 0.052(3) 0.030(3) -0.001(2) 0.011(2) C20 0.042(2) 0.059(3) 0.049(3) 0.007(2) 0.0007(19) 0.000(2) C21 0.051(2) 0.036(2) 0.038(2) 0.0023(16) 0.0022(17) -0.0024(18) C22 0.050(3) 0.043(2) 0.044(2) 0.0002(18) 0.0018(18) -0.0082(19) C23 0.076(3) 0.052(3) 0.042(2) -0.0059(19) 0.011(2) -0.020(2) C24 0.115(4) 0.032(2) 0.048(3) 0.0007(19) 0.015(3) -0.013(3) C25 0.082(3) 0.039(2) 0.048(3) 0.0055(18) 0.015(2) 0.013(2) C26 0.054(3) 0.044(2) 0.044(2) 0.0035(18) 0.0093(19) 0.005(2) C27 0.034(2) 0.043(2) 0.047(2) 0.0071(18) 0.0015(17) 0.0000(16) C28 0.034(2) 0.051(2) 0.057(3) 0.005(2) 0.0012(18) -0.0028(18) C29 0.038(2) 0.054(3) 0.071(3) -0.008(2) 0.003(2) -0.0083(19) C30 0.045(2) 0.039(2) 0.087(4) 0.007(2) 0.012(2) -0.0036(19) C31 0.056(3) 0.054(3) 0.070(3) 0.023(2) 0.006(2) 0.002(2) C32 0.047(2) 0.052(2) 0.053(3) 0.012(2) 0.0038(19) -0.0049(19) B1 0.034(2) 0.038(2) 0.047(3) 0.0041(19) -0.0058(19) -0.0099(18) _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 C30 1.733(4) . ? F1 C10 1.358(5) . ? F2 C11 1.348(5) . ? F3 C12 1.346(5) . ? F4 C13 1.321(5) . ? F5 C14 1.346(4) . ? F6 C16 1.333(5) . ? F7 C17 1.337(5) . ? F8 C18 1.337(5) . ? F9 C19 1.350(5) . ? F10 C20 1.351(5) . ? F11 C22 1.351(4) . ? F12 C23 1.333(5) . ? F13 C24 1.345(5) . ? F14 C25 1.348(5) . ? F15 C26 1.337(5) . ? C1 C2 1.369(5) . ? C1 C21 1.490(5) . ? C1 B1 1.552(6) . ? C2 C27 1.478(5) . ? C2 C3 1.486(5) . ? C3 C4 1.392(6) . ? C3 C8 1.400(6) . ? C4 C5 1.379(6) . ? C5 C6 1.366(8) . ? C6 C7 1.359(8) . ? C7 C8 1.400(7) . ? C9 C10 1.379(5) . ? C9 C14 1.379(5) . ? C9 B1 1.580(6) . ? C10 C11 1.379(6) . ? C11 C12 1.348(6) . ? C12 C13 1.373(6) . ? C13 C14 1.373(6) . ? C15 C20 1.386(5) . ? C15 C16 1.388(5) . ? C15 B1 1.579(5) . ? C16 C17 1.376(6) . ? C17 C18 1.364(7) . ? C18 C19 1.370(7) . ? C19 C20 1.375(6) . ? C21 C22 1.373(5) . ? C21 C26 1.388(5) . ? C22 C23 1.381(6) . ? C23 C24 1.371(7) . ? C24 C25 1.345(6) . ? C25 C26 1.377(6) . ? C27 C32 1.396(5) . ? C27 C28 1.398(5) . ? C28 C29 1.376(5) . ? C29 C30 1.366(6) . ? C30 C31 1.379(6) . ? C31 C32 1.373(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 C2 C1 C21 120.6(3) . . ? C2 C1 B1 121.7(3) . . ? C21 C1 B1 117.5(3) . . ? C1 C2 C27 117.8(3) . . ? C1 C2 C3 124.0(3) . . ? C27 C2 C3 118.1(3) . . ? C4 C3 C8 119.3(4) . . ? C4 C3 C2 120.0(4) . . ? C8 C3 C2 120.6(4) . . ? C5 C4 C3 119.6(5) . . ? C6 C5 C4 121.1(5) . . ? C7 C6 C5 120.2(5) . . ? C6 C7 C8 120.6(5) . . ? C7 C8 C3 119.1(5) . . ? C10 C9 C14 114.5(4) . . ? C10 C9 B1 122.3(4) . . ? C14 C9 B1 123.2(3) . . ? F1 C10 C9 119.7(4) . . ? F1 C10 C11 117.2(4) . . ? C9 C10 C11 123.0(4) . . ? F2 C11 C12 120.4(4) . . ? F2 C11 C10 120.1(4) . . ? C12 C11 C10 119.5(4) . . ? F3 C12 C11 120.5(4) . . ? F3 C12 C13 119.0(4) . . ? C11 C12 C13 120.5(4) . . ? F4 C13 C12 120.4(4) . . ? F4 C13 C14 121.4(4) . . ? C12 C13 C14 118.1(4) . . ? F5 C14 C13 116.8(4) . . ? F5 C14 C9 119.0(3) . . ? C13 C14 C9 124.2(4) . . ? C20 C15 C16 114.8(3) . . ? C20 C15 B1 123.1(3) . . ? C16 C15 B1 122.0(3) . . ? F6 C16 C17 117.1(4) . . ? F6 C16 C15 119.6(3) . . ? C17 C16 C15 123.2(4) . . ? F7 C17 C18 119.9(4) . . ? F7 C17 C16 120.5(5) . . ? C18 C17 C16 119.6(4) . . ? F8 C18 C17 121.0(5) . . ? F8 C18 C19 119.3(5) . . ? C17 C18 C19 119.6(4) . . ? F9 C19 C18 120.7(4) . . ? F9 C19 C20 119.6(5) . . ? C18 C19 C20 119.7(4) . . ? F10 C20 C19 117.2(4) . . ? F10 C20 C15 119.7(3) . . ? C19 C20 C15 123.0(4) . . ? C22 C21 C26 115.7(3) . . ? C22 C21 C1 121.6(3) . . ? C26 C21 C1 122.7(3) . . ? F11 C22 C21 119.0(3) . . ? F11 C22 C23 117.3(4) . . ? C21 C22 C23 123.7(4) . . ? F12 C23 C24 121.1(4) . . ? F12 C23 C22 121.1(4) . . ? C24 C23 C22 117.8(4) . . ? F13 C24 C25 120.6(5) . . ? F13 C24 C23 118.5(5) . . ? C25 C24 C23 120.9(4) . . ? C24 C25 F14 120.4(4) . . ? C24 C25 C26 120.2(4) . . ? F14 C25 C26 119.4(4) . . ? F15 C26 C25 118.4(4) . . ? F15 C26 C21 119.9(3) . . ? C25 C26 C21 121.7(4) . . ? C32 C27 C28 118.4(4) . . ? C32 C27 C2 122.0(3) . . ? C28 C27 C2 119.5(3) . . ? C29 C28 C27 120.7(4) . . ? C30 C29 C28 119.3(4) . . ? C29 C30 C31 121.3(4) . . ? C29 C30 Cl1 119.5(4) . . ? C31 C30 Cl1 119.2(4) . . ? C32 C31 C30 119.5(4) . . ? C31 C32 C27 120.3(4) . . ? C1 B1 C15 119.4(3) . . ? C1 B1 C9 120.9(3) . . ? C15 B1 C9 119.5(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.332 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.056 data_ll009_0m _database_code_depnum_ccdc_archive 'CCDC 893909' #TrackingRef 'all-cifs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H15 B Cl F18' _chemical_formula_weight 835.74 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' B B 0.0013 0.0007 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7455(5) _cell_length_b 16.6985(7) _cell_length_c 18.4110(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.803(2) _cell_angle_gamma 90.00 _cell_volume 3299.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1660 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7124 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28414 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7521 _reflns_number_gt 5627 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1088P)^2^+10.7286P] 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 7521 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 0.647 _refine_ls_restrained_S_all 0.647 _refine_ls_shift/su_max 0.003 _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 B1 B 0.6242(2) 0.72387(15) 0.96873(13) 0.0261(5) Uani 1 1 d . . . Cl1 Cl 1.19713(7) 0.76294(5) 1.05362(5) 0.0593(2) Uani 1 1 d . . . F1 F 0.74525(15) 0.85554(9) 1.04448(9) 0.0438(4) Uani 1 1 d . . . F2 F 0.85570(17) 0.85006(12) 1.17746(9) 0.0589(5) Uani 1 1 d . . . F3 F 0.85524(18) 0.71187(15) 1.25544(9) 0.0684(6) Uani 1 1 d . . . F4 F 0.7429(2) 0.57942(12) 1.19819(9) 0.0652(5) Uani 1 1 d . . . F5 F 0.63277(16) 0.58263(9) 1.06564(8) 0.0437(4) Uani 1 1 d . . . F6 F 0.62228(15) 0.79340(9) 0.82376(7) 0.0394(3) Uani 1 1 d . . . F7 F 0.51002(18) 0.92946(10) 0.78328(9) 0.0561(5) Uani 1 1 d . . . F8 F 0.36956(19) 1.01063(11) 0.87777(13) 0.0692(6) Uani 1 1 d . . . F9 F 0.35031(16) 0.95599(11) 1.01560(11) 0.0600(5) Uani 1 1 d . . . F10 F 0.46842(14) 0.82208(10) 1.05868(8) 0.0420(4) Uani 1 1 d . . . F11 F 0.40754(14) 0.62755(10) 0.97876(7) 0.0415(4) Uani 1 1 d . . . F12 F 0.19251(15) 0.59083(12) 0.90399(9) 0.0546(5) Uani 1 1 d . . . F13 F 0.18724(15) 0.57989(11) 0.75705(9) 0.0530(4) Uani 1 1 d . . . F14 F 0.39959(16) 0.59897(11) 0.68554(8) 0.0503(4) Uani 1 1 d . . . F15 F 0.61529(14) 0.63214(9) 0.75899(7) 0.0387(3) Uani 1 1 d . . . F16 F 0.8838(2) 0.27271(14) 0.77097(15) 0.0902(8) Uani 1 1 d . . . F17 F 0.8192(4) 0.33733(17) 0.67609(14) 0.1181(12) Uani 1 1 d . . . F18 F 0.6927(2) 0.27818(14) 0.74047(17) 0.1007(10) Uani 1 1 d . . . C1 C 0.6833(2) 0.71993(13) 1.04881(12) 0.0282(5) Uani 1 1 d . . . C2 C 0.7415(2) 0.78627(15) 1.08144(13) 0.0327(5) Uani 1 1 d . . . C3 C 0.7993(2) 0.78490(18) 1.14975(14) 0.0408(6) Uani 1 1 d . . . C4 C 0.7990(2) 0.7150(2) 1.18901(13) 0.0455(7) Uani 1 1 d . . . C5 C 0.7418(3) 0.64773(18) 1.15993(13) 0.0426(6) Uani 1 1 d . . . C6 C 0.6859(2) 0.65066(15) 1.09112(12) 0.0334(5) Uani 1 1 d . . . C7 C 0.5500(2) 0.80088(13) 0.94331(12) 0.0282(4) Uani 1 1 d . . . C8 C 0.5551(2) 0.83137(14) 0.87331(13) 0.0314(5) Uani 1 1 d . . . C9 C 0.4982(3) 0.90197(15) 0.85105(15) 0.0409(6) Uani 1 1 d . . . C10 C 0.4273(3) 0.94322(16) 0.89874(18) 0.0459(7) Uani 1 1 d . . . C11 C 0.4177(2) 0.91505(16) 0.96820(17) 0.0420(6) Uani 1 1 d . . . C12 C 0.4794(2) 0.84605(15) 0.98976(14) 0.0335(5) Uani 1 1 d . . . C13 C 0.5196(2) 0.62932(12) 0.87201(11) 0.0251(4) Uani 1 1 d . . . C14 C 0.4080(2) 0.61977(14) 0.90598(12) 0.0293(5) Uani 1 1 d . . . C15 C 0.2973(2) 0.60185(16) 0.86881(14) 0.0351(5) Uani 1 1 d . . . C16 C 0.2945(2) 0.59517(15) 0.79409(14) 0.0362(5) Uani 1 1 d . . . C17 C 0.4026(2) 0.60466(15) 0.75804(12) 0.0338(5) Uani 1 1 d . . . C18 C 0.5129(2) 0.62147(13) 0.79655(12) 0.0284(4) Uani 1 1 d . . . C19 C 0.8597(2) 0.64693(13) 0.94373(11) 0.0256(4) Uani 1 1 d . . . C20 C 0.8922(2) 0.72508(14) 0.92709(12) 0.0311(5) Uani 1 1 d . . . H20A H 0.8426 0.7544 0.8923 0.037 Uiso 1 1 calc R . . C21 C 0.9962(2) 0.76079(15) 0.96067(14) 0.0358(5) Uani 1 1 d . . . H21A H 1.0189 0.8139 0.9485 0.043 Uiso 1 1 calc R . . C22 C 1.0664(2) 0.71816(15) 1.01204(14) 0.0349(5) Uani 1 1 d . . . C23 C 1.0366(2) 0.64021(15) 1.02993(14) 0.0346(5) Uani 1 1 d . . . H23A H 1.0854 0.6118 1.0658 0.042 Uiso 1 1 calc R . . C24 C 0.9338(2) 0.60426(13) 0.99449(13) 0.0297(5) Uani 1 1 d . . . H24A H 0.9139 0.5502 1.0050 0.036 Uiso 1 1 calc R . . C25 C 0.7588(2) 0.53540(13) 0.86885(12) 0.0272(4) Uani 1 1 d . . . C26 C 0.8582(2) 0.52595(15) 0.82337(13) 0.0341(5) Uani 1 1 d . . . H26A H 0.9182 0.5674 0.8200 0.041 Uiso 1 1 calc R . . C27 C 0.8695(3) 0.45656(17) 0.78334(15) 0.0421(6) Uani 1 1 d . . . H27A H 0.9365 0.4506 0.7519 0.051 Uiso 1 1 calc R . . C28 C 0.7832(3) 0.39574(16) 0.78905(15) 0.0403(6) Uani 1 1 d . . . C29 C 0.6868(2) 0.40265(15) 0.83611(14) 0.0372(5) Uani 1 1 d . . . H29A H 0.6297 0.3598 0.8413 0.045 Uiso 1 1 calc R . . C30 C 0.6748(2) 0.47284(14) 0.87555(12) 0.0300(5) Uani 1 1 d . . . H30A H 0.6084 0.4782 0.9074 0.036 Uiso 1 1 calc R . . C31 C 0.6354(2) 0.65135(13) 0.91566(11) 0.0251(4) Uani 1 1 d . . . C32 C 0.7444(2) 0.61139(13) 0.90971(11) 0.0253(4) Uani 1 1 d . . . C33 C 0.7953(3) 0.31997(19) 0.7436(2) 0.0563(8) Uani 1 1 d . . . C34 C 0.8616(8) -0.0479(4) 0.8824(4) 0.139(3) Uani 1 1 d . . . H34A H 0.8186 -0.0345 0.8358 0.209 Uiso 1 1 calc R . . H34B H 0.8002 -0.0545 0.9196 0.209 Uiso 1 1 calc R . . H34C H 0.9080 -0.0980 0.8774 0.209 Uiso 1 1 calc R . . C35 C 0.9373(6) 0.0085(4) 0.9012(3) 0.111(2) Uani 1 1 d . . . H35A H 0.8870 0.0582 0.9003 0.134 Uiso 1 1 calc R . . H35C H 0.9949 0.0134 0.8611 0.134 Uiso 1 1 calc R . . C36 C 1.0138(6) 0.0121(4) 0.9667(3) 0.113(2) Uani 1 1 d . . . H36A H 1.0911 -0.0169 0.9558 0.135 Uiso 1 1 calc R . . H36C H 1.0377 0.0691 0.9722 0.135 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 B1 0.0274(12) 0.0259(12) 0.0254(11) -0.0013(9) 0.0046(9) -0.0040(9) Cl1 0.0424(4) 0.0456(4) 0.0875(6) 0.0040(4) -0.0202(4) -0.0129(3) F1 0.0490(9) 0.0313(8) 0.0507(9) -0.0067(6) -0.0012(7) -0.0100(7) F2 0.0562(10) 0.0719(12) 0.0483(10) -0.0283(9) -0.0015(8) -0.0230(9) F3 0.0600(11) 0.1192(18) 0.0251(8) -0.0015(9) -0.0082(7) -0.0184(11) F4 0.0837(14) 0.0716(13) 0.0392(9) 0.0259(9) -0.0089(9) -0.0117(10) F5 0.0622(10) 0.0320(8) 0.0366(8) 0.0056(6) -0.0028(7) -0.0110(7) F6 0.0530(9) 0.0360(8) 0.0297(7) 0.0035(6) 0.0065(6) 0.0069(7) F7 0.0734(12) 0.0443(9) 0.0493(10) 0.0157(8) -0.0109(8) 0.0078(8) F8 0.0662(12) 0.0388(9) 0.1015(16) 0.0049(10) -0.0074(11) 0.0236(9) F9 0.0461(9) 0.0482(10) 0.0865(13) -0.0251(9) 0.0122(9) 0.0124(8) F10 0.0402(8) 0.0488(9) 0.0380(8) -0.0127(7) 0.0106(6) -0.0009(7) F11 0.0417(8) 0.0605(10) 0.0231(7) -0.0057(6) 0.0092(6) -0.0035(7) F12 0.0320(8) 0.0803(13) 0.0523(10) -0.0076(9) 0.0105(7) -0.0108(8) F13 0.0405(9) 0.0648(11) 0.0521(10) -0.0066(8) -0.0161(7) -0.0071(8) F14 0.0614(10) 0.0677(11) 0.0211(7) -0.0027(7) -0.0060(6) -0.0042(9) F15 0.0405(8) 0.0516(9) 0.0246(6) 0.0014(6) 0.0091(6) -0.0029(7) F16 0.0817(15) 0.0639(14) 0.124(2) -0.0406(13) -0.0109(14) 0.0339(12) F17 0.207(3) 0.0813(17) 0.0692(16) -0.0439(13) 0.0355(19) -0.006(2) F18 0.0798(16) 0.0630(14) 0.159(3) -0.0677(16) 0.0002(16) -0.0060(12) C1 0.0303(11) 0.0285(11) 0.0258(10) -0.0054(8) 0.0033(8) 0.0001(9) C2 0.0318(12) 0.0351(12) 0.0316(12) -0.0081(9) 0.0068(9) -0.0035(10) C3 0.0336(12) 0.0567(17) 0.0325(12) -0.0174(12) 0.0055(10) -0.0107(12) C4 0.0365(13) 0.079(2) 0.0208(11) -0.0058(12) 0.0014(9) -0.0074(13) C5 0.0452(14) 0.0553(16) 0.0274(12) 0.0092(11) 0.0035(10) -0.0049(12) C6 0.0378(12) 0.0367(13) 0.0258(11) -0.0011(9) 0.0039(9) -0.0038(10) C7 0.0263(10) 0.0253(11) 0.0329(11) -0.0050(9) 0.0002(8) -0.0022(8) C8 0.0335(12) 0.0274(11) 0.0330(11) -0.0025(9) -0.0020(9) -0.0002(9) C9 0.0427(14) 0.0312(13) 0.0475(15) 0.0040(11) -0.0104(11) 0.0009(11) C10 0.0395(14) 0.0305(13) 0.0665(18) -0.0024(12) -0.0096(12) 0.0066(11) C11 0.0314(12) 0.0311(13) 0.0636(17) -0.0162(12) 0.0027(11) 0.0020(10) C12 0.0294(11) 0.0314(12) 0.0397(13) -0.0098(10) 0.0031(9) -0.0053(9) C13 0.0317(11) 0.0205(10) 0.0233(10) -0.0016(8) 0.0028(8) 0.0019(8) C14 0.0345(12) 0.0305(11) 0.0232(10) -0.0036(8) 0.0038(8) 0.0002(9) C15 0.0291(11) 0.0384(13) 0.0381(13) -0.0027(10) 0.0059(9) -0.0025(10) C16 0.0356(12) 0.0357(13) 0.0363(12) -0.0033(10) -0.0076(10) -0.0027(10) C17 0.0446(13) 0.0326(12) 0.0235(10) -0.0010(9) -0.0031(9) 0.0009(10) C18 0.0341(11) 0.0271(11) 0.0243(10) -0.0002(8) 0.0040(8) -0.0003(9) C19 0.0282(10) 0.0230(10) 0.0258(10) -0.0005(8) 0.0055(8) 0.0004(8) C20 0.0364(12) 0.0273(11) 0.0296(11) 0.0046(9) 0.0018(9) -0.0022(9) C21 0.0370(13) 0.0267(11) 0.0440(13) 0.0053(10) 0.0039(10) -0.0062(10) C22 0.0272(11) 0.0332(12) 0.0443(13) -0.0031(10) 0.0010(10) -0.0050(9) C23 0.0320(12) 0.0298(12) 0.0415(13) 0.0022(10) -0.0024(10) 0.0025(9) C24 0.0310(11) 0.0221(10) 0.0360(12) 0.0026(9) 0.0020(9) 0.0005(9) C25 0.0316(11) 0.0242(10) 0.0258(10) -0.0004(8) 0.0008(8) 0.0023(9) C26 0.0375(12) 0.0315(12) 0.0340(12) -0.0021(9) 0.0071(10) -0.0010(10) C27 0.0445(14) 0.0432(15) 0.0394(14) -0.0095(11) 0.0097(11) 0.0056(12) C28 0.0453(14) 0.0320(13) 0.0429(14) -0.0119(11) -0.0033(11) 0.0079(11) C29 0.0378(13) 0.0265(12) 0.0465(14) -0.0034(10) -0.0065(10) -0.0015(10) C30 0.0310(11) 0.0271(11) 0.0319(11) 0.0013(9) 0.0007(9) 0.0008(9) C31 0.0310(11) 0.0242(10) 0.0202(9) 0.0018(8) 0.0020(8) -0.0015(8) C32 0.0317(11) 0.0228(10) 0.0215(9) 0.0028(8) 0.0028(8) -0.0008(8) C33 0.0571(18) 0.0418(16) 0.070(2) -0.0228(15) 0.0012(15) 0.0060(14) C34 0.198(8) 0.111(5) 0.109(5) 0.022(4) 0.018(5) 0.038(5) C35 0.115(4) 0.130(5) 0.088(3) -0.021(3) -0.007(3) -0.048(4) C36 0.141(5) 0.115(4) 0.081(3) 0.004(3) -0.015(3) -0.074(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 B1 C31 1.564(3) . ? B1 C7 1.572(3) . ? B1 C1 1.578(3) . ? Cl1 C22 1.736(2) . ? F1 C2 1.344(3) . ? F2 C3 1.335(3) . ? F3 C4 1.338(3) . ? F4 C5 1.340(3) . ? F5 C6 1.345(3) . ? F6 C8 1.349(3) . ? F7 C9 1.341(3) . ? F8 C10 1.333(3) . ? F9 C11 1.347(3) . ? F10 C12 1.341(3) . ? F11 C14 1.346(2) . ? F12 C15 1.339(3) . ? F13 C16 1.335(3) . ? F14 C17 1.337(3) . ? F15 C18 1.340(3) . ? F16 C33 1.317(4) . ? F17 C33 1.313(4) . ? F18 C33 1.304(4) . ? C1 C2 1.394(3) . ? C1 C6 1.394(3) . ? C2 C3 1.375(4) . ? C3 C4 1.373(4) . ? C4 C5 1.377(4) . ? C5 C6 1.376(3) . ? C7 C8 1.389(3) . ? C7 C12 1.393(3) . ? C8 C9 1.381(3) . ? C9 C10 1.375(4) . ? C10 C11 1.371(4) . ? C11 C12 1.378(4) . ? C13 C14 1.389(3) . ? C13 C18 1.394(3) . ? C13 C31 1.494(3) . ? C14 C15 1.376(3) . ? C15 C16 1.379(3) . ? C16 C17 1.375(4) . ? C17 C18 1.379(3) . ? C19 C20 1.389(3) . ? C19 C24 1.394(3) . ? C19 C32 1.484(3) . ? C20 C21 1.385(3) . ? C20 H20A 0.9500 . ? C21 C22 1.378(4) . ? C21 H21A 0.9500 . ? C22 C23 1.384(3) . ? C23 C24 1.391(3) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C30 1.390(3) . ? C25 C26 1.398(3) . ? C25 C32 1.487(3) . ? C26 C27 1.382(4) . ? C26 H26A 0.9500 . ? C27 C28 1.383(4) . ? C27 H27A 0.9500 . ? C28 C29 1.387(4) . ? C28 C33 1.526(4) . ? C29 C30 1.388(3) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C32 1.357(3) . ? C34 C35 1.282(9) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.427(7) . ? C35 H35A 0.9900 . ? C35 H35C 0.9900 . ? C36 C36 1.339(9) 3_757 ? C36 H36A 0.9900 . ? C36 H36C 0.9900 . ? 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 C31 B1 C7 120.05(19) . . ? C31 B1 C1 120.8(2) . . ? C7 B1 C1 119.16(19) . . ? C2 C1 C6 115.0(2) . . ? C2 C1 B1 121.4(2) . . ? C6 C1 B1 123.6(2) . . ? F1 C2 C3 117.0(2) . . ? F1 C2 C1 119.3(2) . . ? C3 C2 C1 123.6(2) . . ? F2 C3 C4 120.3(2) . . ? F2 C3 C2 120.8(3) . . ? C4 C3 C2 118.9(2) . . ? F3 C4 C3 120.2(3) . . ? F3 C4 C5 119.8(3) . . ? C3 C4 C5 120.1(2) . . ? F4 C5 C6 120.4(3) . . ? F4 C5 C4 119.9(2) . . ? C6 C5 C4 119.7(3) . . ? F5 C6 C5 116.7(2) . . ? F5 C6 C1 120.6(2) . . ? C5 C6 C1 122.7(2) . . ? C8 C7 C12 114.7(2) . . ? C8 C7 B1 122.3(2) . . ? C12 C7 B1 122.9(2) . . ? F6 C8 C9 116.4(2) . . ? F6 C8 C7 120.1(2) . . ? C9 C8 C7 123.4(2) . . ? F7 C9 C10 120.2(2) . . ? F7 C9 C8 120.5(2) . . ? C10 C9 C8 119.3(3) . . ? F8 C10 C11 120.3(3) . . ? F8 C10 C9 120.1(3) . . ? C11 C10 C9 119.5(2) . . ? F9 C11 C10 119.8(2) . . ? F9 C11 C12 120.3(3) . . ? C10 C11 C12 119.9(2) . . ? F10 C12 C11 117.3(2) . . ? F10 C12 C7 119.7(2) . . ? C11 C12 C7 123.0(2) . . ? C14 C13 C18 115.7(2) . . ? C14 C13 C31 120.08(19) . . ? C18 C13 C31 124.1(2) . . ? F11 C14 C15 118.1(2) . . ? F11 C14 C13 118.8(2) . . ? C15 C14 C13 123.1(2) . . ? F12 C15 C14 121.1(2) . . ? F12 C15 C16 119.6(2) . . ? C14 C15 C16 119.3(2) . . ? F13 C16 C17 120.3(2) . . ? F13 C16 C15 120.1(2) . . ? C17 C16 C15 119.7(2) . . ? F14 C17 C16 119.6(2) . . ? F14 C17 C18 120.4(2) . . ? C16 C17 C18 120.0(2) . . ? F15 C18 C17 117.92(19) . . ? F15 C18 C13 119.9(2) . . ? C17 C18 C13 122.2(2) . . ? C20 C19 C24 119.1(2) . . ? C20 C19 C32 119.8(2) . . ? C24 C19 C32 121.08(19) . . ? C21 C20 C19 120.8(2) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C22 C21 C20 119.1(2) . . ? C22 C21 H21A 120.5 . . ? C20 C21 H21A 120.5 . . ? C21 C22 C23 121.6(2) . . ? C21 C22 Cl1 118.92(19) . . ? C23 C22 Cl1 119.5(2) . . ? C22 C23 C24 118.8(2) . . ? C22 C23 H23A 120.6 . . ? C24 C23 H23A 120.6 . . ? C23 C24 C19 120.6(2) . . ? C23 C24 H24A 119.7 . . ? C19 C24 H24A 119.7 . . ? C30 C25 C26 119.1(2) . . ? C30 C25 C32 120.8(2) . . ? C26 C25 C32 120.0(2) . . ? C27 C26 C25 120.2(2) . . ? C27 C26 H26A 119.9 . . ? C25 C26 H26A 119.9 . . ? C26 C27 C28 119.9(2) . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C27 C28 C29 120.7(2) . . ? C27 C28 C33 119.4(3) . . ? C29 C28 C33 119.9(3) . . ? C28 C29 C30 119.3(2) . . ? C28 C29 H29A 120.4 . . ? C30 C29 H29A 120.4 . . ? C29 C30 C25 120.7(2) . . ? C29 C30 H30A 119.7 . . ? C25 C30 H30A 119.7 . . ? C32 C31 C13 122.34(19) . . ? C32 C31 B1 121.6(2) . . ? C13 C31 B1 116.02(18) . . ? C31 C32 C19 118.35(19) . . ? C31 C32 C25 124.9(2) . . ? C19 C32 C25 116.73(19) . . ? F18 C33 F17 106.3(3) . . ? F18 C33 F16 106.8(3) . . ? F17 C33 F16 108.9(3) . . ? F18 C33 C28 111.9(3) . . ? F17 C33 C28 111.2(3) . . ? F16 C33 C28 111.5(3) . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C35 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C34 C35 C36 126.2(6) . . ? C34 C35 H35A 105.8 . . ? C36 C35 H35A 105.8 . . ? C34 C35 H35C 105.8 . . ? C36 C35 H35C 105.8 . . ? H35A C35 H35C 106.2 . . ? C36 C36 C35 128.1(7) 3_757 . ? C36 C36 H36A 105.3 3_757 . ? C35 C36 H36A 105.3 . . ? C36 C36 H36C 105.3 3_757 . ? C35 C36 H36C 105.3 . . ? H36A C36 H36C 106.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.378 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.060 data_ll007_0m _database_code_depnum_ccdc_archive 'CCDC 893910' #TrackingRef 'all-cifs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H13 B Cl2 F18 O' _chemical_formula_weight 873.16 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.2093(4) _cell_length_b 13.0466(4) _cell_length_c 22.3254(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.050(2) _cell_angle_gamma 90.00 _cell_volume 3434.23(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7062 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 36446 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6049 _reflns_number_gt 4407 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1142P)^2^+7.9218P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6049 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.2139 _refine_ls_wR_factor_gt 0.1887 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.004 _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 O1 O 0.4025(2) -0.0513(2) 0.59335(13) 0.0309(7) Uani 1 1 d . . . B1 B 0.2295(4) 0.3012(3) 0.41662(19) 0.0214(9) Uani 1 1 d . . . F1 F 0.0339(2) 0.1618(2) 0.37864(10) 0.0337(6) Uani 1 1 d . . . F2 F -0.0793(2) 0.0814(2) 0.45460(12) 0.0439(7) Uani 1 1 d . . . F3 F -0.0223(2) 0.1306(2) 0.57677(12) 0.0446(7) Uani 1 1 d . . . F4 F 0.1524(2) 0.2607(2) 0.62271(11) 0.0433(7) Uani 1 1 d . . . F5 F 0.2730(2) 0.3365(2) 0.54887(10) 0.0360(6) Uani 1 1 d . . . F6 F 0.4470(2) 0.37744(19) 0.40876(13) 0.0398(6) Uani 1 1 d . . . F7 F 0.5197(3) 0.5709(2) 0.42707(19) 0.0687(10) Uani 1 1 d . . . F8 F 0.3869(3) 0.7162(2) 0.45903(17) 0.0643(9) Uani 1 1 d . . . F9 F 0.1772(3) 0.66699(19) 0.46999(13) 0.0453(7) Uani 1 1 d . . . F10 F 0.1003(2) 0.47466(18) 0.44874(12) 0.0366(6) Uani 1 1 d . . . F11 F 0.4179(2) 0.25573(19) 0.28990(11) 0.0346(6) Uani 1 1 d . . . F12 F 0.3945(2) 0.3739(2) 0.18969(13) 0.0513(8) Uani 1 1 d . . . F13 F 0.2063(3) 0.4921(3) 0.14894(14) 0.0583(9) Uani 1 1 d . . . F14 F 0.0413(2) 0.4897(2) 0.20954(13) 0.0517(8) Uani 1 1 d . . . F15 F 0.0629(2) 0.37048(19) 0.31059(11) 0.0361(6) Uani 1 1 d . . . F16 F 0.1728(4) -0.1716(3) 0.13175(16) 0.0759(12) Uani 1 1 d . . . F17 F 0.3237(3) -0.1054(3) 0.11925(15) 0.0723(11) Uani 1 1 d . . . F18 F 0.1653(3) -0.0326(3) 0.08308(13) 0.0732(11) Uani 1 1 d . . . C1 C 0.1587(3) 0.2539(3) 0.46009(17) 0.0220(8) Uani 1 1 d . . . C2 C 0.0679(3) 0.1880(3) 0.43909(17) 0.0224(8) Uani 1 1 d . . . C3 C 0.0074(3) 0.1461(3) 0.4775(2) 0.0281(9) Uani 1 1 d . . . C4 C 0.0358(4) 0.1703(3) 0.5391(2) 0.0309(9) Uani 1 1 d . . . C5 C 0.1246(4) 0.2366(3) 0.56230(18) 0.0276(9) Uani 1 1 d . . . C6 C 0.1839(3) 0.2758(3) 0.52325(18) 0.0248(8) Uani 1 1 d . . . C7 C 0.2703(3) 0.4169(3) 0.42797(17) 0.0239(8) Uani 1 1 d . . . C8 C 0.3766(4) 0.4471(3) 0.4227(2) 0.0306(9) Uani 1 1 d . . . C9 C 0.4162(4) 0.5459(4) 0.4328(2) 0.0418(12) Uani 1 1 d . . . C10 C 0.3485(4) 0.6202(3) 0.4488(2) 0.0401(11) Uani 1 1 d . . . C11 C 0.2431(4) 0.5944(3) 0.45483(19) 0.0328(10) Uani 1 1 d . . . C12 C 0.2055(4) 0.4949(3) 0.44405(18) 0.0262(9) Uani 1 1 d . . . C13 C 0.2395(3) 0.3072(3) 0.30313(17) 0.0213(8) Uani 1 1 d . . . C14 C 0.3230(3) 0.3116(3) 0.27108(18) 0.0256(9) Uani 1 1 d . . . C15 C 0.3130(4) 0.3734(3) 0.2201(2) 0.0324(10) Uani 1 1 d . . . C16 C 0.2179(4) 0.4327(4) 0.1991(2) 0.0365(11) Uani 1 1 d . . . C17 C 0.1339(4) 0.4314(3) 0.2299(2) 0.0332(10) Uani 1 1 d . . . C18 C 0.1463(4) 0.3700(3) 0.28085(18) 0.0269(9) Uani 1 1 d . . . C19 C 0.3105(3) 0.0868(3) 0.41965(17) 0.0201(8) Uani 1 1 d . . . C20 C 0.2721(3) -0.0122(3) 0.42673(18) 0.0239(8) Uani 1 1 d . . . H20A H 0.2270 -0.0473 0.3916 0.029 Uiso 1 1 calc R . . C21 C 0.2987(3) -0.0600(3) 0.48428(18) 0.0240(8) Uani 1 1 d . . . H21A H 0.2698 -0.1263 0.4889 0.029 Uiso 1 1 calc R . . C22 C 0.3681(3) -0.0097(3) 0.53527(17) 0.0227(8) Uani 1 1 d . . . C23 C 0.4097(3) 0.0873(3) 0.52887(18) 0.0248(8) Uani 1 1 d . . . H23A H 0.4572 0.1211 0.5637 0.030 Uiso 1 1 calc R . . C24 C 0.3818(3) 0.1344(3) 0.47166(17) 0.0222(8) Uani 1 1 d . . . H24A H 0.4114 0.2005 0.4674 0.027 Uiso 1 1 calc R . . C25 C 0.2648(3) 0.0819(3) 0.30208(17) 0.0214(8) Uani 1 1 d . . . C26 C 0.3498(4) 0.0165(3) 0.29470(19) 0.0292(9) Uani 1 1 d . . . H26A H 0.4161 0.0076 0.3277 0.035 Uiso 1 1 calc R . . C27 C 0.3387(4) -0.0362(3) 0.2394(2) 0.0331(10) Uani 1 1 d . . . H27A H 0.3982 -0.0795 0.2344 0.040 Uiso 1 1 calc R . . C28 C 0.2414(4) -0.0258(3) 0.19164(18) 0.0282(9) Uani 1 1 d . . . C29 C 0.1542(3) 0.0368(3) 0.19920(18) 0.0276(9) Uani 1 1 d . . . H29A H 0.0863 0.0424 0.1669 0.033 Uiso 1 1 calc R . . C30 C 0.1658(3) 0.0910(3) 0.25354(18) 0.0258(9) Uani 1 1 d . . . H30A H 0.1064 0.1348 0.2581 0.031 Uiso 1 1 calc R . . C31 C 0.2500(3) 0.2438(3) 0.36029(17) 0.0208(8) Uani 1 1 d . . . C32 C 0.2744(3) 0.1413(3) 0.36022(17) 0.0200(8) Uani 1 1 d . . . C33 C 0.3659(4) -0.1522(3) 0.6018(2) 0.0355(10) Uani 1 1 d . . . H33A H 0.3962 -0.1727 0.6452 0.053 Uiso 1 1 calc R . . H33B H 0.3934 -0.1996 0.5749 0.053 Uiso 1 1 calc R . . H33C H 0.2828 -0.1542 0.5912 0.053 Uiso 1 1 calc R . . C34 C 0.2278(4) -0.0835(3) 0.1323(2) 0.0362(10) Uani 1 1 d . . . C35 C 0.1736(7) 0.7312(7) 0.2608(4) 0.092(2) Uani 1 1 d . . . H35A H 0.1792 0.8031 0.2479 0.111 Uiso 1 1 calc R . . H35B H 0.1259 0.6935 0.2249 0.111 Uiso 1 1 calc R . . Cl1 Cl 0.3088(2) 0.67713(19) 0.28076(11) 0.1053(7) Uani 1 1 d . . . Cl2 Cl 0.10801(17) 0.72893(19) 0.32067(9) 0.0902(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0360(16) 0.0338(17) 0.0219(14) 0.0071(12) 0.0055(12) 0.0028(13) B1 0.021(2) 0.021(2) 0.020(2) 0.0012(17) 0.0017(17) -0.0010(17) F1 0.0359(13) 0.0429(15) 0.0219(12) -0.0114(10) 0.0069(10) -0.0138(11) F2 0.0376(14) 0.0525(17) 0.0435(15) -0.0132(13) 0.0141(12) -0.0270(13) F3 0.0512(16) 0.0527(17) 0.0391(15) -0.0017(13) 0.0283(13) -0.0188(13) F4 0.0639(18) 0.0497(17) 0.0182(12) -0.0062(11) 0.0140(12) -0.0163(14) F5 0.0403(14) 0.0405(14) 0.0241(12) -0.0058(11) 0.0028(10) -0.0221(12) F6 0.0310(13) 0.0276(13) 0.0651(18) -0.0059(12) 0.0200(12) -0.0033(11) F7 0.0439(17) 0.0423(18) 0.124(3) -0.0115(18) 0.0301(19) -0.0222(14) F8 0.077(2) 0.0202(14) 0.096(3) -0.0140(15) 0.0231(19) -0.0169(14) F9 0.0701(19) 0.0236(13) 0.0471(16) -0.0051(12) 0.0239(14) 0.0086(13) F10 0.0397(14) 0.0290(13) 0.0469(15) -0.0022(11) 0.0215(12) 0.0034(11) F11 0.0285(12) 0.0396(14) 0.0376(14) 0.0129(11) 0.0121(11) 0.0064(11) F12 0.0395(15) 0.076(2) 0.0438(16) 0.0285(15) 0.0204(13) 0.0010(14) F13 0.0568(18) 0.073(2) 0.0461(17) 0.0420(16) 0.0149(14) 0.0081(16) F14 0.0538(17) 0.0532(18) 0.0475(17) 0.0245(14) 0.0121(14) 0.0265(14) F15 0.0402(14) 0.0387(14) 0.0342(13) 0.0061(11) 0.0183(11) 0.0129(11) F16 0.123(3) 0.058(2) 0.058(2) -0.0306(17) 0.042(2) -0.041(2) F17 0.058(2) 0.106(3) 0.058(2) -0.045(2) 0.0252(16) -0.0022(19) F18 0.113(3) 0.075(2) 0.0252(15) -0.0118(15) 0.0052(17) 0.024(2) C1 0.027(2) 0.0175(19) 0.0219(19) 0.0001(15) 0.0062(16) 0.0000(15) C2 0.0241(19) 0.023(2) 0.0201(19) -0.0058(16) 0.0064(15) -0.0004(16) C3 0.025(2) 0.027(2) 0.033(2) -0.0056(18) 0.0092(17) -0.0076(17) C4 0.034(2) 0.032(2) 0.032(2) -0.0013(18) 0.0187(19) -0.0054(18) C5 0.036(2) 0.028(2) 0.0191(19) -0.0018(16) 0.0070(17) -0.0047(18) C6 0.028(2) 0.021(2) 0.024(2) -0.0026(16) 0.0034(16) -0.0062(16) C7 0.033(2) 0.020(2) 0.0183(18) -0.0008(15) 0.0067(16) -0.0032(17) C8 0.035(2) 0.021(2) 0.037(2) -0.0042(18) 0.0104(19) -0.0041(18) C9 0.037(3) 0.032(3) 0.057(3) 0.000(2) 0.013(2) -0.013(2) C10 0.054(3) 0.014(2) 0.049(3) -0.0054(19) 0.009(2) -0.010(2) C11 0.054(3) 0.019(2) 0.025(2) -0.0017(17) 0.0094(19) 0.0047(19) C12 0.034(2) 0.021(2) 0.024(2) 0.0003(16) 0.0079(17) 0.0013(17) C13 0.027(2) 0.0154(18) 0.0212(19) -0.0011(15) 0.0058(16) -0.0036(15) C14 0.026(2) 0.025(2) 0.024(2) 0.0045(16) 0.0038(16) -0.0003(17) C15 0.030(2) 0.038(3) 0.030(2) 0.0083(19) 0.0106(18) -0.0072(19) C16 0.041(3) 0.037(3) 0.029(2) 0.0169(19) 0.005(2) -0.003(2) C17 0.038(2) 0.028(2) 0.031(2) 0.0071(18) 0.0037(19) 0.0064(19) C18 0.035(2) 0.022(2) 0.025(2) 0.0002(16) 0.0096(17) 0.0021(17) C19 0.0255(19) 0.0156(19) 0.0207(19) 0.0012(15) 0.0089(15) 0.0026(15) C20 0.030(2) 0.020(2) 0.0215(19) -0.0025(16) 0.0065(16) -0.0009(16) C21 0.031(2) 0.0162(19) 0.026(2) 0.0022(15) 0.0099(17) 0.0012(16) C22 0.0243(19) 0.027(2) 0.0182(18) 0.0033(16) 0.0086(15) 0.0073(16) C23 0.026(2) 0.029(2) 0.0195(19) -0.0020(16) 0.0043(16) 0.0006(17) C24 0.026(2) 0.0180(19) 0.023(2) -0.0009(15) 0.0065(16) -0.0005(15) C25 0.031(2) 0.0165(19) 0.0189(18) 0.0029(15) 0.0094(16) -0.0021(16) C26 0.034(2) 0.026(2) 0.025(2) 0.0011(17) 0.0025(17) 0.0039(18) C27 0.037(2) 0.030(2) 0.033(2) -0.0060(19) 0.0118(19) 0.0047(19) C28 0.037(2) 0.026(2) 0.022(2) -0.0016(17) 0.0095(18) -0.0055(18) C29 0.028(2) 0.028(2) 0.025(2) -0.0033(17) 0.0031(17) -0.0039(17) C30 0.026(2) 0.026(2) 0.026(2) -0.0013(17) 0.0075(16) -0.0012(16) C31 0.0239(19) 0.0172(19) 0.0202(19) 0.0027(15) 0.0039(15) -0.0035(15) C32 0.0216(18) 0.0190(19) 0.0193(18) 0.0007(15) 0.0053(15) -0.0043(15) C33 0.043(3) 0.035(2) 0.030(2) 0.0097(19) 0.012(2) 0.005(2) C34 0.047(3) 0.032(2) 0.032(2) -0.0077(19) 0.016(2) -0.004(2) C35 0.090(5) 0.096(6) 0.087(5) 0.029(5) 0.016(4) -0.010(5) Cl1 0.1089(16) 0.1111(17) 0.0953(15) 0.0100(13) 0.0253(13) 0.0189(14) Cl2 0.0803(12) 0.1236(17) 0.0676(11) 0.0122(11) 0.0209(9) -0.0046(11) _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 O1 C22 1.367(5) . ? O1 C33 1.419(5) . ? B1 C31 1.540(6) . ? B1 C1 1.583(6) . ? B1 C7 1.588(6) . ? F1 C2 1.349(4) . ? F2 C3 1.346(5) . ? F3 C4 1.338(5) . ? F4 C5 1.340(5) . ? F5 C6 1.347(4) . ? F6 C8 1.342(5) . ? F7 C9 1.343(5) . ? F8 C10 1.336(5) . ? F9 C11 1.342(5) . ? F10 C12 1.342(5) . ? F11 C14 1.341(5) . ? F12 C15 1.343(5) . ? F13 C16 1.339(5) . ? F14 C17 1.340(5) . ? F15 C18 1.352(5) . ? F16 C34 1.330(5) . ? F17 C34 1.309(5) . ? F18 C34 1.339(6) . ? C1 C2 1.385(5) . ? C1 C6 1.393(5) . ? C2 C3 1.382(6) . ? C3 C4 1.365(6) . ? C4 C5 1.378(6) . ? C5 C6 1.369(6) . ? C7 C8 1.390(6) . ? C7 C12 1.392(6) . ? C8 C9 1.375(6) . ? C9 C10 1.380(7) . ? C10 C11 1.370(7) . ? C11 C12 1.377(6) . ? C13 C18 1.386(6) . ? C13 C14 1.390(5) . ? C13 C31 1.498(5) . ? C14 C15 1.374(6) . ? C15 C16 1.372(6) . ? C16 C17 1.375(6) . ? C17 C18 1.367(6) . ? C19 C20 1.396(5) . ? C19 C24 1.402(5) . ? C19 C32 1.469(5) . ? C20 C21 1.389(5) . ? C20 H20A 0.9500 . ? C21 C22 1.394(6) . ? C21 H21A 0.9500 . ? C22 C23 1.385(6) . ? C23 C24 1.378(5) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C26 1.387(6) . ? C25 C30 1.403(6) . ? C25 C32 1.490(5) . ? C26 C27 1.387(6) . ? C26 H26A 0.9500 . ? C27 C28 1.382(6) . ? C27 H27A 0.9500 . ? C28 C29 1.386(6) . ? C28 C34 1.495(6) . ? C29 C30 1.379(6) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C32 1.370(5) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C35 Cl2 1.726(8) . ? C35 Cl1 1.744(8) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? 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 C22 O1 C33 117.7(3) . . ? C31 B1 C1 122.8(3) . . ? C31 B1 C7 118.8(3) . . ? C1 B1 C7 118.1(3) . . ? C2 C1 C6 114.6(3) . . ? C2 C1 B1 123.4(3) . . ? C6 C1 B1 121.9(3) . . ? F1 C2 C3 116.5(3) . . ? F1 C2 C1 120.4(3) . . ? C3 C2 C1 123.1(4) . . ? F2 C3 C4 119.8(4) . . ? F2 C3 C2 120.4(4) . . ? C4 C3 C2 119.7(4) . . ? F3 C4 C3 120.4(4) . . ? F3 C4 C5 120.1(4) . . ? C3 C4 C5 119.6(4) . . ? F4 C5 C6 121.1(4) . . ? F4 C5 C4 119.6(4) . . ? C6 C5 C4 119.3(4) . . ? F5 C6 C5 116.8(3) . . ? F5 C6 C1 119.5(3) . . ? C5 C6 C1 123.6(4) . . ? C8 C7 C12 114.8(4) . . ? C8 C7 B1 121.2(4) . . ? C12 C7 B1 124.0(4) . . ? F6 C8 C9 117.0(4) . . ? F6 C8 C7 119.7(3) . . ? C9 C8 C7 123.3(4) . . ? F7 C9 C8 120.7(4) . . ? F7 C9 C10 119.8(4) . . ? C8 C9 C10 119.5(4) . . ? F8 C10 C11 120.8(4) . . ? F8 C10 C9 119.6(4) . . ? C11 C10 C9 119.6(4) . . ? F9 C11 C10 119.4(4) . . ? F9 C11 C12 121.0(4) . . ? C10 C11 C12 119.6(4) . . ? F10 C12 C11 117.0(4) . . ? F10 C12 C7 119.7(4) . . ? C11 C12 C7 123.3(4) . . ? C18 C13 C14 115.8(3) . . ? C18 C13 C31 120.9(3) . . ? C14 C13 C31 123.3(3) . . ? F11 C14 C15 117.5(4) . . ? F11 C14 C13 120.4(3) . . ? C15 C14 C13 122.1(4) . . ? F12 C15 C16 119.8(4) . . ? F12 C15 C14 120.2(4) . . ? C16 C15 C14 120.0(4) . . ? F13 C16 C15 120.6(4) . . ? F13 C16 C17 119.6(4) . . ? C15 C16 C17 119.8(4) . . ? F14 C17 C18 121.1(4) . . ? F14 C17 C16 119.8(4) . . ? C18 C17 C16 119.2(4) . . ? F15 C18 C17 118.1(4) . . ? F15 C18 C13 118.7(3) . . ? C17 C18 C13 123.2(4) . . ? C20 C19 C24 118.0(3) . . ? C20 C19 C32 121.3(3) . . ? C24 C19 C32 120.6(3) . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20A 119.5 . . ? C19 C20 H20A 119.5 . . ? C20 C21 C22 119.4(4) . . ? C20 C21 H21A 120.3 . . ? C22 C21 H21A 120.3 . . ? O1 C22 C23 115.5(3) . . ? O1 C22 C21 124.0(4) . . ? C23 C22 C21 120.5(3) . . ? C24 C23 C22 119.6(4) . . ? C24 C23 H23A 120.2 . . ? C22 C23 H23A 120.2 . . ? C23 C24 C19 121.4(4) . . ? C23 C24 H24A 119.3 . . ? C19 C24 H24A 119.3 . . ? C26 C25 C30 118.8(4) . . ? C26 C25 C32 122.1(3) . . ? C30 C25 C32 119.1(3) . . ? C25 C26 C27 120.5(4) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? C27 C28 C29 119.8(4) . . ? C27 C28 C34 120.7(4) . . ? C29 C28 C34 119.5(4) . . ? C30 C29 C28 120.1(4) . . ? C30 C29 H29A 119.9 . . ? C28 C29 H29A 119.9 . . ? C29 C30 C25 120.5(4) . . ? C29 C30 H30A 119.8 . . ? C25 C30 H30A 119.8 . . ? C32 C31 C13 120.6(3) . . ? C32 C31 B1 123.9(3) . . ? C13 C31 B1 115.5(3) . . ? C31 C32 C19 119.1(3) . . ? C31 C32 C25 122.7(3) . . ? C19 C32 C25 118.2(3) . . ? O1 C33 H33A 109.5 . . ? O1 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O1 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? F17 C34 F16 106.7(4) . . ? F17 C34 F18 106.1(4) . . ? F16 C34 F18 104.0(4) . . ? F17 C34 C28 114.0(4) . . ? F16 C34 C28 112.5(4) . . ? F18 C34 C28 112.7(4) . . ? Cl2 C35 Cl1 113.2(4) . . ? Cl2 C35 H35A 108.9 . . ? Cl1 C35 H35A 108.9 . . ? Cl2 C35 H35B 108.9 . . ? Cl1 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.543 _refine_diff_density_min -0.941 _refine_diff_density_rms 0.088 #===end