# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name W.Piers _publ_contact_author_address ; Department of Chemistry University of Calgary 2500 University Drive NW Calgary Alberta T2N 1N4 CANADA ; _publ_contact_author_email WPIERS@UCALGARY.CA _publ_section_title ; 2,2'-Disubstituted F12Binaphthyl Derivatives: Stannanes, Boranes, and (R)-F12BINOL ; loop_ _publ_author_name W.Piers 'Robert McDonald' 'Darryl J. Morrison' 'Masood Parvez' 'Susanne D. Riegel' data_cal0511 _database_code_depnum_ccdc_archive 'CCDC 299722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 2,2'-dihydroxy-3,3',4,4',5,5',6,6',7,7',8,8'-dodecafluoro- 1,1'-binaphthyl bis(diethylether) adduct ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 F12 O4' _chemical_formula_weight 650.46 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' O O 0.0106 0.0060 '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 10.9881(9) _cell_length_b 20.1333(16) _cell_length_c 12.9050(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.3641(14) _cell_angle_gamma 90.00 _cell_volume 2777.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.79 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9289 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21180 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5687 _reflns_number_gt 3339 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0628P)^2^+0.5368P] 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 5687 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 F13 F -0.06757(13) 0.19681(7) 0.30956(12) 0.0722(4) Uani 1 1 d . . . F14 F -0.03136(13) 0.12038(7) 0.48117(12) 0.0696(4) Uani 1 1 d . . . F16 F 0.09781(14) 0.03100(7) 0.60061(11) 0.0676(4) Uani 1 1 d . . . F17 F 0.28719(15) -0.05622(7) 0.63512(11) 0.0718(4) Uani 1 1 d . . . F18 F 0.43154(12) -0.06906(6) 0.49328(11) 0.0630(4) Uani 1 1 d . . . F19 F 0.39766(12) 0.00679(6) 0.32182(10) 0.0555(3) Uani 1 1 d . . . F23 F 0.54367(13) 0.20366(7) 0.15308(12) 0.0726(4) Uani 1 1 d . . . F24 F 0.51838(12) 0.12265(7) -0.01223(11) 0.0662(4) Uani 1 1 d . . . F26 F 0.40195(14) 0.02641(7) -0.12431(11) 0.0694(4) Uani 1 1 d . . . F27 F 0.22433(16) -0.06789(7) -0.15104(12) 0.0803(5) Uani 1 1 d . . . F28 F 0.07871(14) -0.08043(7) -0.01041(11) 0.0739(4) Uani 1 1 d . . . F29 F 0.10185(13) 0.00052(6) 0.15402(10) 0.0608(4) Uani 1 1 d . . . O1 O 0.08643(15) 0.18955(7) 0.16974(13) 0.0554(4) Uani 1 1 d . . . H1O H 0.0296 0.2170 0.1723 0.083 Uiso 1 1 calc R . . O2 O 0.39007(16) 0.19476(8) 0.29261(13) 0.0610(5) Uani 1 1 d . . . H2O H 0.4528 0.2191 0.2949 0.091 Uiso 1 1 calc R . . C11 C 0.20228(19) 0.10486(9) 0.27254(16) 0.0397(5) Uani 1 1 d . . . C12 C 0.1056(2) 0.14995(10) 0.25582(17) 0.0449(5) Uani 1 1 d . . . C13 C 0.0275(2) 0.15301(10) 0.32803(18) 0.0508(6) Uani 1 1 d . . . C14 C 0.0461(2) 0.11373(10) 0.41498(18) 0.0492(5) Uani 1 1 d . . . C15 C 0.1441(2) 0.06739(10) 0.43763(16) 0.0450(5) Uani 1 1 d . . . C16 C 0.1694(2) 0.02628(11) 0.52917(17) 0.0500(6) Uani 1 1 d . . . C17 C 0.2633(2) -0.01815(11) 0.54780(17) 0.0518(6) Uani 1 1 d . . . C18 C 0.3384(2) -0.02432(10) 0.47458(18) 0.0493(5) Uani 1 1 d . . . C19 C 0.3192(2) 0.01499(10) 0.38707(17) 0.0446(5) Uani 1 1 d . . . C20 C 0.22275(19) 0.06272(9) 0.36390(16) 0.0401(5) Uani 1 1 d . . . C21 C 0.28454(18) 0.10529(9) 0.19527(16) 0.0394(5) Uani 1 1 d . . . C22 C 0.3764(2) 0.15302(10) 0.20971(17) 0.0451(5) Uani 1 1 d . . . C23 C 0.4539(2) 0.15686(10) 0.13710(18) 0.0490(5) Uani 1 1 d . . . C24 C 0.4406(2) 0.11542(11) 0.05356(17) 0.0465(5) Uani 1 1 d . . . C25 C 0.34811(19) 0.06610(10) 0.03356(16) 0.0425(5) Uani 1 1 d . . . C26 C 0.3295(2) 0.02170(11) -0.05381(17) 0.0512(6) Uani 1 1 d . . . C27 C 0.2412(2) -0.02581(11) -0.06841(18) 0.0564(6) Uani 1 1 d . . . C28 C 0.1657(2) -0.03228(10) 0.00389(19) 0.0540(6) Uani 1 1 d . . . C29 C 0.1787(2) 0.00973(10) 0.08799(17) 0.0476(5) Uani 1 1 d . . . C30 C 0.26923(19) 0.06109(9) 0.10728(16) 0.0407(5) Uani 1 1 d . . . O1S O -0.06815(14) 0.29475(7) 0.14040(12) 0.0544(4) Uani 1 1 d . . . C1S C -0.1956(3) 0.28913(15) 0.0907(3) 0.0988(11) Uani 1 1 d . . . H1SA H -0.2246 0.3311 0.0530 0.119 Uiso 1 1 calc R . . H1SB H -0.2441 0.2822 0.1456 0.119 Uiso 1 1 calc R . . C2S C -0.2193(3) 0.23465(17) 0.0155(2) 0.0946(10) Uani 1 1 d . . . H2SA H -0.3089 0.2327 -0.0180 0.114 Uiso 1 1 calc R . . H2SB H -0.1931 0.1929 0.0530 0.114 Uiso 1 1 calc R . . H2SC H -0.1720 0.2415 -0.0393 0.114 Uiso 1 1 calc R . . C3S C -0.0417(3) 0.34965(12) 0.2117(2) 0.0723(8) Uani 1 1 d . . . H3SA H -0.0863 0.3441 0.2696 0.087 Uiso 1 1 calc R . . H3SB H -0.0713 0.3913 0.1732 0.087 Uiso 1 1 calc R . . C4S C 0.0936(3) 0.35377(14) 0.2571(2) 0.0738(8) Uani 1 1 d . . . H4SA H 0.1111 0.3910 0.3072 0.089 Uiso 1 1 calc R . . H4SB H 0.1372 0.3606 0.1998 0.089 Uiso 1 1 calc R . . H4SC H 0.1226 0.3124 0.2947 0.089 Uiso 1 1 calc R . . O2S O 0.56255(14) 0.29154(7) 0.34281(12) 0.0543(4) Uani 1 1 d . . . C5S C 0.5497(2) 0.35528(12) 0.2956(2) 0.0666(7) Uani 1 1 d . . . H5SA H 0.6146 0.3615 0.2546 0.080 Uiso 1 1 calc R . . H5SB H 0.5622 0.3896 0.3521 0.080 Uiso 1 1 calc R . . C6S C 0.4263(3) 0.36337(14) 0.2251(2) 0.0831(8) Uani 1 1 d . . . H6SA H 0.4207 0.4071 0.1910 0.100 Uiso 1 1 calc R . . H6SB H 0.3622 0.3597 0.2664 0.100 Uiso 1 1 calc R . . H6SC H 0.4130 0.3287 0.1703 0.100 Uiso 1 1 calc R . . C7S C 0.6755(3) 0.28228(14) 0.4190(2) 0.0779(8) Uani 1 1 d . . . H7SA H 0.6811 0.3150 0.4772 0.094 Uiso 1 1 calc R . . H7SB H 0.7467 0.2901 0.3855 0.094 Uiso 1 1 calc R . . C8S C 0.6838(3) 0.21502(15) 0.4631(3) 0.0975(10) Uani 1 1 d . . . H8SA H 0.7641 0.2095 0.5145 0.117 Uiso 1 1 calc R . . H8SB H 0.6775 0.1826 0.4055 0.117 Uiso 1 1 calc R . . H8SC H 0.6153 0.2079 0.4989 0.117 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 F13 0.0698(9) 0.0666(9) 0.0922(11) 0.0204(8) 0.0433(8) 0.0223(8) F14 0.0723(9) 0.0723(9) 0.0792(10) 0.0117(7) 0.0481(8) 0.0071(7) F16 0.0843(10) 0.0680(9) 0.0614(9) 0.0077(7) 0.0396(8) -0.0038(8) F17 0.0944(11) 0.0709(9) 0.0519(8) 0.0175(7) 0.0207(8) 0.0040(8) F18 0.0634(9) 0.0614(8) 0.0620(9) 0.0105(7) 0.0099(7) 0.0104(7) F19 0.0586(8) 0.0565(8) 0.0552(8) 0.0060(6) 0.0209(6) 0.0111(6) F23 0.0701(9) 0.0753(10) 0.0837(10) -0.0210(8) 0.0411(8) -0.0343(8) F24 0.0654(9) 0.0763(9) 0.0680(9) -0.0081(7) 0.0383(7) -0.0069(7) F26 0.0850(10) 0.0720(9) 0.0599(9) -0.0115(7) 0.0345(8) 0.0053(8) F27 0.1159(13) 0.0659(9) 0.0591(9) -0.0253(7) 0.0203(8) -0.0091(9) F28 0.0926(11) 0.0558(8) 0.0708(10) -0.0176(7) 0.0139(8) -0.0259(8) F29 0.0739(9) 0.0541(8) 0.0585(8) -0.0091(6) 0.0240(7) -0.0273(7) O1 0.0630(11) 0.0468(9) 0.0622(10) 0.0115(7) 0.0266(8) 0.0105(7) O2 0.0684(11) 0.0594(10) 0.0638(11) -0.0231(8) 0.0332(9) -0.0277(8) C11 0.0437(12) 0.0328(10) 0.0445(12) -0.0043(9) 0.0140(10) -0.0089(9) C12 0.0510(13) 0.0360(11) 0.0504(13) 0.0006(9) 0.0173(10) -0.0067(10) C13 0.0513(14) 0.0417(12) 0.0642(15) 0.0015(11) 0.0229(12) 0.0015(11) C14 0.0520(13) 0.0463(12) 0.0572(14) -0.0018(10) 0.0288(11) -0.0090(11) C15 0.0515(13) 0.0386(11) 0.0471(13) -0.0032(9) 0.0159(10) -0.0107(10) C16 0.0586(14) 0.0503(13) 0.0462(13) -0.0023(10) 0.0231(11) -0.0123(12) C17 0.0635(15) 0.0484(13) 0.0427(13) 0.0051(10) 0.0102(11) -0.0097(12) C18 0.0522(14) 0.0438(12) 0.0505(14) 0.0001(10) 0.0085(11) -0.0003(11) C19 0.0463(13) 0.0445(12) 0.0440(12) -0.0039(10) 0.0127(10) -0.0068(10) C20 0.0437(12) 0.0337(10) 0.0442(12) -0.0048(9) 0.0125(9) -0.0104(9) C21 0.0445(12) 0.0321(10) 0.0429(12) -0.0003(8) 0.0127(10) -0.0023(9) C22 0.0506(13) 0.0397(11) 0.0485(13) -0.0041(10) 0.0184(10) -0.0041(10) C23 0.0478(13) 0.0457(12) 0.0571(14) -0.0043(10) 0.0195(11) -0.0113(10) C24 0.0444(12) 0.0503(12) 0.0504(13) 0.0026(10) 0.0224(10) 0.0028(10) C25 0.0478(12) 0.0378(11) 0.0422(12) 0.0027(9) 0.0112(10) 0.0074(10) C26 0.0622(15) 0.0487(13) 0.0443(13) 0.0007(10) 0.0156(11) 0.0128(12) C27 0.0761(17) 0.0455(13) 0.0452(13) -0.0095(10) 0.0093(12) 0.0030(12) C28 0.0659(15) 0.0386(12) 0.0533(14) -0.0042(10) 0.0055(12) -0.0100(11) C29 0.0581(14) 0.0396(11) 0.0454(13) 0.0007(9) 0.0127(11) -0.0035(10) C30 0.0462(12) 0.0337(10) 0.0419(12) 0.0028(8) 0.0097(9) 0.0036(9) O1S 0.0556(10) 0.0486(9) 0.0569(10) 0.0038(7) 0.0089(8) 0.0055(8) C1S 0.071(2) 0.0663(19) 0.138(3) -0.0044(19) -0.020(2) 0.0104(16) C2S 0.088(2) 0.122(3) 0.070(2) -0.0042(19) 0.0100(17) -0.032(2) C3S 0.0766(19) 0.0539(15) 0.093(2) -0.0123(14) 0.0328(16) -0.0050(14) C4S 0.084(2) 0.0698(17) 0.0656(17) -0.0009(13) 0.0133(15) -0.0159(15) O2S 0.0558(10) 0.0449(9) 0.0583(10) -0.0001(7) 0.0051(8) -0.0102(7) C5S 0.0646(17) 0.0519(14) 0.0873(19) 0.0056(13) 0.0255(15) -0.0025(13) C6S 0.090(2) 0.0741(18) 0.081(2) 0.0068(15) 0.0092(17) 0.0054(16) C7S 0.0698(19) 0.0695(18) 0.087(2) 0.0001(15) 0.0029(16) -0.0049(15) C8S 0.104(2) 0.090(2) 0.093(2) 0.0216(18) 0.0116(19) 0.0269(19) _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 F13 C13 1.345(2) . ? F14 C14 1.344(2) . ? F16 C16 1.347(2) . ? F17 C17 1.338(2) . ? F18 C18 1.343(2) . ? F19 C19 1.347(2) . ? F23 C23 1.345(2) . ? F24 C24 1.345(2) . ? F26 C26 1.343(2) . ? F27 C27 1.341(2) . ? F28 C28 1.344(2) . ? F29 C29 1.344(2) . ? O1 C12 1.344(2) . ? O2 C22 1.341(2) . ? C11 C12 1.376(3) . ? C11 C20 1.428(3) . ? C11 C21 1.493(3) . ? C12 C13 1.407(3) . ? C13 C14 1.349(3) . ? C14 C15 1.404(3) . ? C15 C16 1.416(3) . ? C15 C20 1.429(3) . ? C16 C17 1.344(3) . ? C17 C18 1.397(3) . ? C18 C19 1.355(3) . ? C19 C20 1.410(3) . ? C21 C22 1.374(3) . ? C21 C30 1.422(3) . ? C22 C23 1.407(3) . ? C23 C24 1.344(3) . ? C24 C25 1.401(3) . ? C25 C26 1.416(3) . ? C25 C30 1.431(3) . ? C26 C27 1.344(3) . ? C27 C28 1.391(3) . ? C28 C29 1.357(3) . ? C29 C30 1.417(3) . ? O1S C1S 1.404(3) . ? O1S C3S 1.425(3) . ? C1S C2S 1.447(4) . ? C3S C4S 1.468(4) . ? O2S C7S 1.407(3) . ? O2S C5S 1.414(3) . ? C5S C6S 1.457(4) . ? C7S C8S 1.464(4) . ? 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 C12 C11 C20 119.34(18) . . ? C12 C11 C21 117.15(18) . . ? C20 C11 C21 123.44(18) . . ? O1 C12 C11 119.25(18) . . ? O1 C12 C13 121.25(19) . . ? C11 C12 C13 119.49(19) . . ? F13 C13 C14 119.59(19) . . ? F13 C13 C12 118.61(19) . . ? C14 C13 C12 121.8(2) . . ? F14 C14 C13 118.3(2) . . ? F14 C14 C15 120.10(19) . . ? C13 C14 C15 121.63(19) . . ? C14 C15 C16 123.8(2) . . ? C14 C15 C20 117.27(19) . . ? C16 C15 C20 119.0(2) . . ? C17 C16 F16 118.0(2) . . ? C17 C16 C15 122.2(2) . . ? F16 C16 C15 119.8(2) . . ? F17 C17 C16 121.7(2) . . ? F17 C17 C18 119.2(2) . . ? C16 C17 C18 119.2(2) . . ? F18 C18 C19 120.5(2) . . ? F18 C18 C17 118.9(2) . . ? C19 C18 C17 120.6(2) . . ? F19 C19 C18 116.75(19) . . ? F19 C19 C20 120.60(18) . . ? C18 C19 C20 122.65(19) . . ? C19 C20 C11 123.18(18) . . ? C19 C20 C15 116.37(18) . . ? C11 C20 C15 120.45(19) . . ? C22 C21 C30 119.58(18) . . ? C22 C21 C11 116.89(17) . . ? C30 C21 C11 123.49(17) . . ? O2 C22 C21 119.34(18) . . ? O2 C22 C23 121.54(18) . . ? C21 C22 C23 119.12(19) . . ? C24 C23 F23 119.86(19) . . ? C24 C23 C22 121.98(19) . . ? F23 C23 C22 118.16(18) . . ? C23 C24 F24 118.15(19) . . ? C23 C24 C25 121.83(19) . . ? F24 C24 C25 120.01(19) . . ? C24 C25 C26 124.0(2) . . ? C24 C25 C30 116.89(18) . . ? C26 C25 C30 119.1(2) . . ? F26 C26 C27 118.5(2) . . ? F26 C26 C25 119.7(2) . . ? C27 C26 C25 121.8(2) . . ? F27 C27 C26 121.6(2) . . ? F27 C27 C28 118.7(2) . . ? C26 C27 C28 119.7(2) . . ? F28 C28 C29 119.9(2) . . ? F28 C28 C27 119.4(2) . . ? C29 C28 C27 120.6(2) . . ? F29 C29 C28 117.13(19) . . ? F29 C29 C30 120.52(18) . . ? C28 C29 C30 122.3(2) . . ? C29 C30 C21 123.09(19) . . ? C29 C30 C25 116.32(18) . . ? C21 C30 C25 120.58(18) . . ? C1S O1S C3S 113.0(2) . . ? O1S C1S C2S 111.9(3) . . ? O1S C3S C4S 109.8(2) . . ? C7S O2S C5S 113.94(19) . . ? O2S C5S C6S 110.9(2) . . ? O2S C7S C8S 111.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 C11 C12 O1 -179.97(18) . . . . ? C21 C11 C12 O1 2.9(3) . . . . ? C20 C11 C12 C13 -1.0(3) . . . . ? C21 C11 C12 C13 -178.13(18) . . . . ? O1 C12 C13 F13 -0.2(3) . . . . ? C11 C12 C13 F13 -179.14(18) . . . . ? O1 C12 C13 C14 -179.7(2) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? F13 C13 C14 F14 -0.6(3) . . . . ? C12 C13 C14 F14 178.90(19) . . . . ? F13 C13 C14 C15 -179.90(19) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? F14 C14 C15 C16 -1.0(3) . . . . ? C13 C14 C15 C16 178.3(2) . . . . ? F14 C14 C15 C20 179.87(18) . . . . ? C13 C14 C15 C20 -0.9(3) . . . . ? C14 C15 C16 C17 179.2(2) . . . . ? C20 C15 C16 C17 -1.6(3) . . . . ? C14 C15 C16 F16 -0.5(3) . . . . ? C20 C15 C16 F16 178.62(18) . . . . ? F16 C16 C17 F17 -0.9(3) . . . . ? C15 C16 C17 F17 179.28(19) . . . . ? F16 C16 C17 C18 179.59(19) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? F17 C17 C18 F18 0.9(3) . . . . ? C16 C17 C18 F18 -179.59(19) . . . . ? F17 C17 C18 C19 -177.9(2) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? F18 C18 C19 F19 -0.2(3) . . . . ? C17 C18 C19 F19 178.55(19) . . . . ? F18 C18 C19 C20 -179.98(17) . . . . ? C17 C18 C19 C20 -1.2(3) . . . . ? F19 C19 C20 C11 -0.3(3) . . . . ? C18 C19 C20 C11 179.38(19) . . . . ? F19 C19 C20 C15 179.67(17) . . . . ? C18 C19 C20 C15 -0.6(3) . . . . ? C12 C11 C20 C19 179.76(18) . . . . ? C21 C11 C20 C19 -3.3(3) . . . . ? C12 C11 C20 C15 -0.3(3) . . . . ? C21 C11 C20 C15 176.69(18) . . . . ? C14 C15 C20 C19 -178.85(18) . . . . ? C16 C15 C20 C19 1.9(3) . . . . ? C14 C15 C20 C11 1.2(3) . . . . ? C16 C15 C20 C11 -178.04(18) . . . . ? C12 C11 C21 C22 80.5(2) . . . . ? C20 C11 C21 C22 -96.5(2) . . . . ? C12 C11 C21 C30 -97.1(2) . . . . ? C20 C11 C21 C30 85.9(3) . . . . ? C30 C21 C22 O2 179.73(19) . . . . ? C11 C21 C22 O2 2.0(3) . . . . ? C30 C21 C22 C23 -0.3(3) . . . . ? C11 C21 C22 C23 -178.05(19) . . . . ? O2 C22 C23 C24 -179.7(2) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? O2 C22 C23 F23 0.3(3) . . . . ? C21 C22 C23 F23 -179.59(19) . . . . ? F23 C23 C24 F24 -0.3(3) . . . . ? C22 C23 C24 F24 179.76(19) . . . . ? F23 C23 C24 C25 -179.76(19) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? C23 C24 C25 C26 179.4(2) . . . . ? F24 C24 C25 C26 -0.1(3) . . . . ? C23 C24 C25 C30 -0.9(3) . . . . ? F24 C24 C25 C30 179.65(18) . . . . ? C24 C25 C26 F26 -1.1(3) . . . . ? C30 C25 C26 F26 179.18(18) . . . . ? C24 C25 C26 C27 178.5(2) . . . . ? C30 C25 C26 C27 -1.2(3) . . . . ? F26 C26 C27 F27 -0.1(3) . . . . ? C25 C26 C27 F27 -179.75(19) . . . . ? F26 C26 C27 C28 179.4(2) . . . . ? C25 C26 C27 C28 -0.3(4) . . . . ? F27 C27 C28 F28 0.3(3) . . . . ? C26 C27 C28 F28 -179.1(2) . . . . ? F27 C27 C28 C29 -179.2(2) . . . . ? C26 C27 C28 C29 1.3(4) . . . . ? F28 C28 C29 F29 0.1(3) . . . . ? C27 C28 C29 F29 179.7(2) . . . . ? F28 C28 C29 C30 179.63(19) . . . . ? C27 C28 C29 C30 -0.8(3) . . . . ? F29 C29 C30 C21 -0.1(3) . . . . ? C28 C29 C30 C21 -179.6(2) . . . . ? F29 C29 C30 C25 178.89(18) . . . . ? C28 C29 C30 C25 -0.7(3) . . . . ? C22 C21 C30 C29 178.67(19) . . . . ? C11 C21 C30 C29 -3.8(3) . . . . ? C22 C21 C30 C25 -0.3(3) . . . . ? C11 C21 C30 C25 177.27(18) . . . . ? C24 C25 C30 C29 -178.13(18) . . . . ? C26 C25 C30 C29 1.6(3) . . . . ? C24 C25 C30 C21 0.9(3) . . . . ? C26 C25 C30 C21 -179.38(18) . . . . ? C3S O1S C1S C2S 177.7(3) . . . . ? C1S O1S C3S C4S -177.8(2) . . . . ? C7S O2S C5S C6S -174.8(2) . . . . ? C5S O2S C7S C8S -178.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O1S 0.84 1.89 2.686(2) 157.9 . O2 H2O O2S 0.84 1.90 2.691(2) 155.7 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.222 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.040 # Attachment 'cmpd3.cif' data_t15 _database_code_depnum_ccdc_archive 'CCDC 299723' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 3,3',4,4',5,5',6,6',7,7',8,8'-dodecafluoro-1,1'-binaphthyl _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H2 F12' _chemical_formula_weight 470.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 13.1128(2) _cell_length_b 23.9042(5) _cell_length_c 10.1940(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3195.32(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.955 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8107 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 30.01 _reflns_number_total 4604 _reflns_number_gt 3298 _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^)+(0.0660P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4604 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 F1 F -0.04139(8) 0.25800(4) 0.35901(10) 0.0436(3) Uani 1 1 d . . . F2 F 0.06193(8) 0.32983(4) 0.51091(10) 0.0454(3) Uani 1 1 d . . . F3 F 0.19628(8) 0.34661(4) 0.68862(10) 0.0465(3) Uani 1 1 d . . . F4 F 0.31904(8) 0.30508(4) 0.87577(10) 0.0485(3) Uani 1 1 d . . . F5 F 0.33072(8) 0.19408(4) 0.91770(10) 0.0447(3) Uani 1 1 d . . . F6 F 0.23214(7) 0.12196(4) 0.76459(10) 0.0398(2) Uani 1 1 d . . . F7 F 0.24820(8) -0.00763(4) 0.36558(10) 0.0436(3) Uani 1 1 d . . . F8 F 0.16092(9) -0.07542(4) 0.54162(10) 0.0452(3) Uani 1 1 d . . . F9 F 0.04883(9) -0.08757(4) 0.74738(10) 0.0482(3) Uani 1 1 d . . . F10 F -0.08197(9) -0.04266(5) 0.92035(10) 0.0507(3) Uani 1 1 d . . . F11 F -0.11495(8) 0.06824(4) 0.92621(10) 0.0463(3) Uani 1 1 d . . . F12 F -0.02565(7) 0.13630(4) 0.75412(9) 0.0378(2) Uani 1 1 d . . . C1 C 0.10029(11) 0.15858(6) 0.55393(14) 0.0272(3) Uani 1 1 d . . . C2 C 0.03666(12) 0.18050(6) 0.46121(14) 0.0299(3) Uani 1 1 d . . . H2 H 0.0006 0.1562 0.4039 0.036 Uiso 1 1 calc R . . C3 C 0.02409(12) 0.23840(6) 0.44971(15) 0.0312(3) Uani 1 1 d . . . C4 C 0.07605(12) 0.27472(6) 0.52672(15) 0.0312(3) Uani 1 1 d . . . C5 C 0.14474(11) 0.25487(6) 0.62304(14) 0.0285(3) Uani 1 1 d . . . C6 C 0.20253(12) 0.29089(6) 0.70387(15) 0.0334(3) Uani 1 1 d . . . C7 C 0.26493(12) 0.27067(7) 0.79915(16) 0.0349(3) Uani 1 1 d . . . C8 C 0.27247(12) 0.21294(7) 0.81941(15) 0.0329(3) Uani 1 1 d . . . C9 C 0.22079(11) 0.17671(6) 0.74034(15) 0.0295(3) Uani 1 1 d . . . C10 C 0.15561(11) 0.19535(6) 0.63904(14) 0.0266(3) Uani 1 1 d . . . C11 C 0.11248(11) 0.09585(6) 0.55679(14) 0.0269(3) Uani 1 1 d . . . C12 C 0.17331(12) 0.07210(6) 0.46303(14) 0.0306(3) Uani 1 1 d . . . H12 H 0.2056 0.0951 0.3995 0.037 Uiso 1 1 calc R . . C13 C 0.18837(12) 0.01397(6) 0.45992(15) 0.0321(3) Uani 1 1 d . . . C14 C 0.14415(12) -0.02028(6) 0.54921(15) 0.0317(3) Uani 1 1 d . . . C15 C 0.07906(11) 0.00149(6) 0.64772(14) 0.0287(3) Uani 1 1 d . . . C16 C 0.03032(13) -0.03229(6) 0.74276(15) 0.0339(3) Uani 1 1 d . . . C17 C -0.03460(13) -0.01030(7) 0.83233(15) 0.0368(4) Uani 1 1 d . . . C18 C -0.05267(12) 0.04769(7) 0.83449(15) 0.0333(3) Uani 1 1 d . . . C19 C -0.00613(12) 0.08162(6) 0.74657(14) 0.0298(3) Uani 1 1 d . . . C20 C 0.06166(11) 0.06087(5) 0.64974(13) 0.0265(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0478(6) 0.0341(5) 0.0489(5) 0.0102(4) -0.0149(5) 0.0029(4) F2 0.0613(7) 0.0206(4) 0.0543(6) 0.0037(4) -0.0061(5) 0.0027(4) F3 0.0642(7) 0.0234(4) 0.0519(6) -0.0051(4) -0.0007(5) -0.0089(4) F4 0.0486(6) 0.0426(5) 0.0542(6) -0.0179(5) -0.0075(5) -0.0109(5) F5 0.0400(6) 0.0481(6) 0.0459(5) -0.0083(4) -0.0154(4) 0.0032(4) F6 0.0436(5) 0.0274(4) 0.0482(5) 0.0000(4) -0.0149(4) 0.0026(4) F7 0.0462(6) 0.0373(5) 0.0473(5) -0.0107(4) 0.0105(4) 0.0095(4) F8 0.0582(7) 0.0223(4) 0.0551(6) -0.0032(4) -0.0005(5) 0.0080(4) F9 0.0745(8) 0.0226(4) 0.0476(6) 0.0047(4) -0.0063(5) -0.0045(4) F10 0.0640(7) 0.0438(6) 0.0442(5) 0.0119(4) 0.0053(5) -0.0143(5) F11 0.0445(6) 0.0513(6) 0.0430(5) 0.0023(4) 0.0140(5) 0.0001(5) F12 0.0422(5) 0.0274(4) 0.0439(5) -0.0025(4) 0.0089(4) 0.0036(4) C1 0.0264(7) 0.0229(6) 0.0323(7) -0.0006(5) 0.0023(5) -0.0012(5) C2 0.0295(7) 0.0259(6) 0.0344(7) 0.0009(5) -0.0012(6) -0.0010(5) C3 0.0303(7) 0.0279(7) 0.0353(7) 0.0057(6) -0.0016(6) 0.0019(6) C4 0.0354(8) 0.0203(6) 0.0380(7) 0.0025(5) 0.0049(6) 0.0004(5) C5 0.0287(7) 0.0237(6) 0.0329(7) -0.0020(5) 0.0068(6) -0.0027(5) C6 0.0371(8) 0.0244(6) 0.0386(8) -0.0051(6) 0.0073(7) -0.0045(6) C7 0.0312(8) 0.0339(7) 0.0397(8) -0.0124(6) 0.0037(6) -0.0075(6) C8 0.0272(8) 0.0368(8) 0.0348(7) -0.0051(6) -0.0021(6) 0.0006(6) C9 0.0274(7) 0.0253(6) 0.0360(7) -0.0014(6) -0.0003(6) 0.0006(5) C10 0.0246(7) 0.0236(6) 0.0315(7) -0.0012(5) 0.0040(5) -0.0009(5) C11 0.0266(7) 0.0229(6) 0.0312(6) -0.0007(5) -0.0049(5) 0.0004(5) C12 0.0302(8) 0.0286(7) 0.0331(7) -0.0020(6) -0.0001(6) 0.0013(6) C13 0.0312(8) 0.0306(7) 0.0345(7) -0.0071(6) -0.0007(6) 0.0044(6) C14 0.0355(8) 0.0213(6) 0.0383(8) -0.0044(6) -0.0083(6) 0.0033(5) C15 0.0305(7) 0.0223(6) 0.0332(7) -0.0007(5) -0.0088(6) -0.0023(5) C16 0.0430(9) 0.0223(6) 0.0363(8) 0.0018(6) -0.0091(7) -0.0049(6) C17 0.0414(9) 0.0354(8) 0.0336(7) 0.0061(6) -0.0047(7) -0.0100(7) C18 0.0296(8) 0.0381(8) 0.0323(7) -0.0009(6) 0.0013(6) -0.0024(6) C19 0.0315(8) 0.0245(6) 0.0335(7) -0.0009(5) -0.0022(6) -0.0002(5) C20 0.0274(7) 0.0228(6) 0.0292(6) -0.0011(5) -0.0059(5) -0.0009(5) _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 F1 C3 1.3460(17) . ? F2 C4 1.3400(15) . ? F3 C6 1.3434(17) . ? F4 C7 1.3379(17) . ? F5 C8 1.3382(18) . ? F6 C9 1.3402(16) . ? F7 C13 1.3443(17) . ? F8 C14 1.3387(15) . ? F9 C16 1.3443(16) . ? F10 C17 1.3376(18) . ? F11 C18 1.3351(18) . ? F12 C19 1.3342(15) . ? C1 C2 1.365(2) . ? C1 C10 1.4324(19) . ? C1 C11 1.5083(19) . ? C2 C3 1.3988(19) . ? C3 C4 1.354(2) . ? C4 C5 1.414(2) . ? C5 C6 1.412(2) . ? C5 C10 1.4391(18) . ? C6 C7 1.359(2) . ? C7 C8 1.399(2) . ? C8 C9 1.363(2) . ? C9 C10 1.413(2) . ? C11 C12 1.368(2) . ? C11 C20 1.429(2) . ? C12 C13 1.404(2) . ? C13 C14 1.355(2) . ? C14 C15 1.417(2) . ? C15 C16 1.414(2) . ? C15 C20 1.4377(18) . ? C16 C17 1.355(2) . ? C17 C18 1.406(2) . ? C18 C19 1.354(2) . ? C19 C20 1.418(2) . ? 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 C10 119.56(13) . . ? C2 C1 C11 117.36(12) . . ? C10 C1 C11 123.00(12) . . ? C1 C2 C3 120.64(13) . . ? F1 C3 C4 119.73(13) . . ? F1 C3 C2 118.50(13) . . ? C4 C3 C2 121.77(14) . . ? F2 C4 C3 119.40(14) . . ? F2 C4 C5 120.09(13) . . ? C3 C4 C5 120.51(13) . . ? C6 C5 C4 122.83(13) . . ? C6 C5 C10 118.91(14) . . ? C4 C5 C10 118.26(13) . . ? F3 C6 C7 118.17(13) . . ? F3 C6 C5 120.28(14) . . ? C7 C6 C5 121.55(14) . . ? F4 C7 C6 121.19(14) . . ? F4 C7 C8 118.87(15) . . ? C6 C7 C8 119.93(14) . . ? F5 C8 C9 120.81(14) . . ? F5 C8 C7 118.90(13) . . ? C9 C8 C7 120.29(14) . . ? F6 C9 C8 117.14(13) . . ? F6 C9 C10 120.67(12) . . ? C8 C9 C10 122.17(13) . . ? C9 C10 C1 123.75(12) . . ? C9 C10 C5 117.05(13) . . ? C1 C10 C5 119.20(13) . . ? C12 C11 C20 119.50(13) . . ? C12 C11 C1 117.44(13) . . ? C20 C11 C1 123.04(12) . . ? C11 C12 C13 120.56(14) . . ? F7 C13 C14 119.89(13) . . ? F7 C13 C12 118.58(13) . . ? C14 C13 C12 121.52(14) . . ? F8 C14 C13 119.08(14) . . ? F8 C14 C15 120.10(13) . . ? C13 C14 C15 120.81(13) . . ? C16 C15 C14 123.24(13) . . ? C16 C15 C20 118.83(14) . . ? C14 C15 C20 117.92(13) . . ? F9 C16 C17 118.12(13) . . ? F9 C16 C15 120.25(14) . . ? C17 C16 C15 121.62(13) . . ? F10 C17 C16 121.30(14) . . ? F10 C17 C18 118.77(15) . . ? C16 C17 C18 119.94(14) . . ? F11 C18 C19 121.25(14) . . ? F11 C18 C17 118.47(14) . . ? C19 C18 C17 120.27(14) . . ? F12 C19 C18 117.53(13) . . ? F12 C19 C20 120.21(12) . . ? C18 C19 C20 122.26(13) . . ? C19 C20 C11 123.32(12) . . ? C19 C20 C15 117.06(13) . . ? C11 C20 C15 119.62(13) . . ? 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 C10 C1 C2 C3 -0.8(2) . . . . ? C11 C1 C2 C3 -177.88(13) . . . . ? C1 C2 C3 F1 -178.36(13) . . . . ? C1 C2 C3 C4 1.8(2) . . . . ? F1 C3 C4 F2 -0.4(2) . . . . ? C2 C3 C4 F2 179.39(14) . . . . ? F1 C3 C4 C5 179.64(13) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? F2 C4 C5 C6 -1.4(2) . . . . ? C3 C4 C5 C6 178.52(14) . . . . ? F2 C4 C5 C10 178.41(13) . . . . ? C3 C4 C5 C10 -1.6(2) . . . . ? C4 C5 C6 F3 -2.1(2) . . . . ? C10 C5 C6 F3 178.03(13) . . . . ? C4 C5 C6 C7 177.35(14) . . . . ? C10 C5 C6 C7 -2.5(2) . . . . ? F3 C6 C7 F4 -0.2(2) . . . . ? C5 C6 C7 F4 -179.65(14) . . . . ? F3 C6 C7 C8 179.10(14) . . . . ? C5 C6 C7 C8 -0.4(2) . . . . ? F4 C7 C8 F5 2.3(2) . . . . ? C6 C7 C8 F5 -176.94(14) . . . . ? F4 C7 C8 C9 -177.94(14) . . . . ? C6 C7 C8 C9 2.8(2) . . . . ? F5 C8 C9 F6 -0.8(2) . . . . ? C7 C8 C9 F6 179.45(14) . . . . ? F5 C8 C9 C10 177.50(13) . . . . ? C7 C8 C9 C10 -2.2(2) . . . . ? F6 C9 C10 C1 -1.9(2) . . . . ? C8 C9 C10 C1 179.87(14) . . . . ? F6 C9 C10 C5 177.60(12) . . . . ? C8 C9 C10 C5 -0.7(2) . . . . ? C2 C1 C10 C9 178.04(14) . . . . ? C11 C1 C10 C9 -5.0(2) . . . . ? C2 C1 C10 C5 -1.4(2) . . . . ? C11 C1 C10 C5 175.50(13) . . . . ? C6 C5 C10 C9 3.0(2) . . . . ? C4 C5 C10 C9 -176.89(13) . . . . ? C6 C5 C10 C1 -177.55(13) . . . . ? C4 C5 C10 C1 2.6(2) . . . . ? C2 C1 C11 C12 76.80(18) . . . . ? C10 C1 C11 C12 -100.17(16) . . . . ? C2 C1 C11 C20 -101.47(16) . . . . ? C10 C1 C11 C20 81.55(19) . . . . ? C20 C11 C12 C13 -1.8(2) . . . . ? C1 C11 C12 C13 179.83(13) . . . . ? C11 C12 C13 F7 179.57(13) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? F7 C13 C14 F8 -0.1(2) . . . . ? C12 C13 C14 F8 179.89(13) . . . . ? F7 C13 C14 C15 -178.62(13) . . . . ? C12 C13 C14 C15 1.3(2) . . . . ? F8 C14 C15 C16 1.0(2) . . . . ? C13 C14 C15 C16 179.53(14) . . . . ? F8 C14 C15 C20 -178.56(12) . . . . ? C13 C14 C15 C20 0.0(2) . . . . ? C14 C15 C16 F9 3.6(2) . . . . ? C20 C15 C16 F9 -176.83(13) . . . . ? C14 C15 C16 C17 -177.36(15) . . . . ? C20 C15 C16 C17 2.2(2) . . . . ? F9 C16 C17 F10 -2.3(2) . . . . ? C15 C16 C17 F10 178.69(14) . . . . ? F9 C16 C17 C18 177.28(13) . . . . ? C15 C16 C17 C18 -1.8(2) . . . . ? F10 C17 C18 F11 1.3(2) . . . . ? C16 C17 C18 F11 -178.23(14) . . . . ? F10 C17 C18 C19 -179.85(14) . . . . ? C16 C17 C18 C19 0.6(2) . . . . ? F11 C18 C19 F12 -0.7(2) . . . . ? C17 C18 C19 F12 -179.49(13) . . . . ? F11 C18 C19 C20 178.90(13) . . . . ? C17 C18 C19 C20 0.1(2) . . . . ? F12 C19 C20 C11 0.2(2) . . . . ? C18 C19 C20 C11 -179.34(14) . . . . ? F12 C19 C20 C15 179.92(12) . . . . ? C18 C19 C20 C15 0.3(2) . . . . ? C12 C11 C20 C19 -177.22(14) . . . . ? C1 C11 C20 C19 1.0(2) . . . . ? C12 C11 C20 C15 3.1(2) . . . . ? C1 C11 C20 C15 -178.66(13) . . . . ? C16 C15 C20 C19 -1.4(2) . . . . ? C14 C15 C20 C19 178.14(13) . . . . ? C16 C15 C20 C11 178.26(13) . . . . ? C14 C15 C20 C11 -2.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.279 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.049 # Attachment 'cmpd5.cif' #------------------------------------------------------------------------------ data_Compound_I _database_code_depnum_ccdc_archive 'CCDC 299724' #----------------------------------------------------------------------------- _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #----------------------------------------------------------------------------- _chemical_name_systematic ; ? ; _chemical_name_common ;2-Bromoboryl-3,3',4,4',5,5',6,6',7,7',8,8'-dodecafluoro-1,1'- binaphthyl dimer ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H16 B2 Br2 F24' _chemical_formula_weight 1302.11 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.880(6) _cell_length_b 12.916(9) _cell_length_c 25.835(10) _cell_angle_alpha 90.00 _cell_angle_beta 126.545(16) _cell_angle_gamma 90.00 _cell_volume 9619(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 26643 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.1 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5088 _exptl_absorpt_coefficient_mu 1.820 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7353 _exptl_absorpt_correction_T_max 0.7847 _exptl_absorpt_process_details 'SORTAV: (Blessing, 1997)' _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method ' \w and \f ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26643 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.13 _reflns_number_total 8475 _reflns_number_gt 5869 _reflns_threshold_expression >2sigma(I) _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^)+(0.092P)^2^+62.20P] 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 8475 _refine_ls_number_parameters 736 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2114 _refine_ls_wR_factor_gt 0.1888 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 Br1 Br 0.26295(2) 0.26411(6) 0.21728(4) 0.0598(3) Uani 1 1 d . . . Br2 Br -0.01019(2) 0.24183(6) -0.00876(4) 0.0537(3) Uani 1 1 d . . . B1 B 0.1970(2) 0.2573(6) 0.1616(3) 0.0347(16) Uani 1 1 d . . . B2 B 0.0557(2) 0.2453(5) 0.0455(3) 0.0334(15) Uani 1 1 d . . . C1 C 0.1693(2) 0.3468(5) 0.1641(3) 0.0337(14) Uani 1 1 d . . . C2 C 0.1796(2) 0.4524(5) 0.1599(3) 0.0368(14) Uani 1 1 d . . . C3 C 0.1550(2) 0.5323(5) 0.1577(3) 0.0416(16) Uani 1 1 d . . . C4 C 0.1171(2) 0.5163(5) 0.1614(3) 0.0426(16) Uani 1 1 d . . . C5 C 0.0893(3) 0.5982(5) 0.1584(3) 0.0500(19) Uani 1 1 d . . . C6 C 0.0526(3) 0.5806(7) 0.1584(3) 0.061(2) Uani 1 1 d . . . C7 C 0.0415(2) 0.4792(7) 0.1639(3) 0.054(2) Uani 1 1 d . . . C8 C 0.0684(2) 0.4005(6) 0.1698(3) 0.0429(16) Uani 1 1 d . . . C9 C 0.1061(2) 0.4131(5) 0.1668(3) 0.0350(14) Uani 1 1 d . . . C10 C 0.1332(2) 0.3293(5) 0.1685(3) 0.0318(13) Uani 1 1 d . . . C11 C 0.1196(2) 0.2194(4) 0.1674(3) 0.0297(13) Uani 1 1 d . . . C12 C 0.14495(19) 0.1564(5) 0.2240(3) 0.0295(13) Uani 1 1 d . . . C13 C 0.1828(2) 0.1929(5) 0.2855(3) 0.0397(15) Uani 1 1 d . . . C14 C 0.2080(2) 0.1292(6) 0.3368(3) 0.0492(18) Uani 1 1 d . . . C15 C 0.1965(2) 0.0242(6) 0.3307(3) 0.0470(17) Uani 1 1 d . . . C16 C 0.1606(2) -0.0151(5) 0.2749(3) 0.0420(16) Uani 1 1 d . . . C17 C 0.1333(2) 0.0493(5) 0.2199(3) 0.0367(14) Uani 1 1 d . . . C18 C 0.0951(2) 0.0118(5) 0.1594(3) 0.0411(15) Uani 1 1 d . . . C19 C 0.0715(2) 0.0743(5) 0.1080(3) 0.0384(15) Uani 1 1 d . . . C20 C 0.08211(19) 0.1791(5) 0.1081(3) 0.0314(13) Uani 1 1 d . . . F1 F 0.21291(13) 0.4733(3) 0.15286(19) 0.0511(10) Uani 1 1 d . . . F2 F 0.16427(16) 0.6274(3) 0.1493(2) 0.0599(11) Uani 1 1 d . . . F3 F 0.10094(18) 0.6978(3) 0.1563(2) 0.0731(14) Uani 1 1 d . . . F4 F 0.02621(18) 0.6588(4) 0.1538(2) 0.0867(17) Uani 1 1 d . . . F5 F 0.00508(15) 0.4646(4) 0.1646(2) 0.0740(14) Uani 1 1 d . . . F6 F 0.05798(14) 0.3048(3) 0.1798(2) 0.0562(11) Uani 1 1 d . . . F7 F 0.19450(14) 0.2931(3) 0.29446(17) 0.0542(10) Uani 1 1 d . . . F8 F 0.24440(15) 0.1657(4) 0.39403(18) 0.0722(13) Uani 1 1 d . . . F9 F 0.22293(14) -0.0369(4) 0.38303(18) 0.0628(12) Uani 1 1 d . . . F10 F 0.15031(14) -0.1156(3) 0.2722(2) 0.0565(11) Uani 1 1 d . . . F11 F 0.08334(15) -0.0887(3) 0.1534(2) 0.0603(11) Uani 1 1 d . . . F12 F 0.03680(14) 0.0304(3) 0.05140(19) 0.0566(11) Uani 1 1 d . . . C21 C 0.08023(19) 0.3153(5) 0.0247(3) 0.0297(13) Uani 1 1 d . . . C22 C 0.0673(2) 0.4187(5) 0.0066(3) 0.0373(15) Uani 1 1 d . . . C23 C 0.0897(2) 0.4859(5) -0.0065(3) 0.0384(15) Uani 1 1 d . . . C24 C 0.1274(2) 0.4533(5) -0.0047(3) 0.0345(14) Uani 1 1 d . . . C25 C 0.1527(2) 0.5205(5) -0.0167(3) 0.0397(15) Uani 1 1 d . . . C26 C 0.1887(2) 0.4859(5) -0.0156(3) 0.0407(16) Uani 1 1 d . . . C27 C 0.2013(2) 0.3814(5) -0.0039(3) 0.0363(14) Uani 1 1 d . . . C28 C 0.1783(2) 0.3154(5) 0.0083(3) 0.0342(14) Uani 1 1 d . . . C29 C 0.14108(19) 0.3463(4) 0.0098(2) 0.0284(13) Uani 1 1 d . . . C30 C 0.1181(2) 0.2806(4) 0.0271(3) 0.0293(13) Uani 1 1 d . . . C31 C 0.13504(19) 0.1725(4) 0.0514(3) 0.0272(12) Uani 1 1 d . . . C32 C 0.1106(2) 0.0843(5) 0.0112(3) 0.0364(14) Uani 1 1 d . . . C33 C 0.0719(2) 0.0918(5) -0.0548(3) 0.0400(15) Uani 1 1 d . . . C34 C 0.0473(2) 0.0073(6) -0.0897(3) 0.0505(18) Uani 1 1 d . . . C35 C 0.0606(3) -0.0907(6) -0.0631(4) 0.055(2) Uani 1 1 d . . . C36 C 0.0981(3) -0.1039(5) -0.0018(4) 0.0497(18) Uani 1 1 d . . . C37 C 0.1244(2) -0.0173(5) 0.0379(3) 0.0391(15) Uani 1 1 d . . . C38 C 0.1631(2) -0.0266(5) 0.1027(3) 0.0428(16) Uani 1 1 d . . . C39 C 0.1859(2) 0.0595(5) 0.1391(3) 0.0375(15) Uani 1 1 d . . . C40 C 0.17310(19) 0.1607(5) 0.1161(3) 0.0308(13) Uani 1 1 d . . . F13 F 0.03222(13) 0.4578(3) 0.0066(2) 0.0543(10) Uani 1 1 d . . . F14 F 0.07524(14) 0.5839(3) -0.0200(2) 0.0556(11) Uani 1 1 d . . . F15 F 0.14077(15) 0.6206(3) -0.0300(2) 0.0565(11) Uani 1 1 d . . . F16 F 0.21294(14) 0.5510(3) -0.02540(19) 0.0544(10) Uani 1 1 d . . . F17 F 0.23588(14) 0.3501(3) -0.0053(2) 0.0534(10) Uani 1 1 d . . . F18 F 0.19112(13) 0.2147(3) 0.01811(19) 0.0452(9) Uani 1 1 d . . . F19 F 0.05920(13) 0.1839(3) -0.08459(17) 0.0502(10) Uani 1 1 d . . . F20 F 0.01040(15) 0.0186(4) -0.1518(2) 0.0678(13) Uani 1 1 d . . . F21 F 0.03617(18) -0.1729(4) -0.1000(2) 0.0789(15) Uani 1 1 d . . . F22 F 0.11074(17) -0.1994(3) 0.0223(2) 0.0663(12) Uani 1 1 d . . . F23 F 0.17690(16) -0.1200(3) 0.1303(2) 0.0645(12) Uani 1 1 d . . . F24 F 0.22146(13) 0.0429(3) 0.20187(18) 0.0512(10) Uani 1 1 d . . . C41 C 0.1569(3) 0.5503(6) 0.3335(3) 0.056(2) Uani 1 1 d . . . C42 C 0.1386(4) 0.6497(7) 0.3285(4) 0.072(3) Uani 1 1 d . . . H42 H 0.1550 0.7090 0.3302 0.086 Uiso 1 1 calc R . . C43 C 0.0980(4) 0.6632(9) 0.3213(5) 0.086(3) Uani 1 1 d . . . H43 H 0.0868 0.7310 0.3186 0.104 Uiso 1 1 calc R . . C44 C 0.0731(4) 0.5777(9) 0.3178(4) 0.081(3) Uani 1 1 d . . . H44 H 0.0452 0.5861 0.3137 0.097 Uiso 1 1 calc R . . C45 C 0.0894(3) 0.4840(7) 0.3204(4) 0.062(2) Uani 1 1 d . . . H45 H 0.0721 0.4252 0.3168 0.075 Uiso 1 1 calc R . . C46 C 0.1300(3) 0.4687(7) 0.3280(3) 0.057(2) Uani 1 1 d . . . H46 H 0.1401 0.4000 0.3295 0.068 Uiso 1 1 calc R . . C47 C 0.2014(3) 0.5368(8) 0.3431(5) 0.080(3) Uani 1 1 d . . . H47A H 0.2145 0.6048 0.3458 0.120 Uiso 1 1 calc R . . H47B H 0.1963 0.4980 0.3068 0.120 Uiso 1 1 calc R . . H47C H 0.2229 0.4985 0.3832 0.120 Uiso 1 1 calc R . . C48 C 0.1605(4) 1.1179(9) 0.4321(6) 0.084(3) Uani 1 1 d . . . C49 C 0.1619(5) 1.0112(9) 0.4333(7) 0.093(4) Uani 1 1 d . . . H49 H 0.1858 0.9763 0.4715 0.111 Uiso 1 1 calc R . . C50 C 0.1312(5) 0.9585(9) 0.3831(8) 0.096(4) Uani 1 1 d . . . H50 H 0.1340 0.8852 0.3845 0.115 Uiso 1 1 calc R . . C51 C 0.0953(4) 1.0029(9) 0.3289(6) 0.084(3) Uani 1 1 d . . . H51 H 0.0722 0.9616 0.2935 0.100 Uiso 1 1 calc R . . C52 C 0.0924(4) 1.1106(12) 0.3253(6) 0.107(4) Uani 1 1 d . . . C53 C 0.1274(3) 1.1707(7) 0.3818(5) 0.072(2) Uani 1 1 d . . . H53 H 0.1263 1.2442 0.3822 0.087 Uiso 1 1 calc R . . C54 C 0.1952(3) 1.1647(7) 0.4905(5) 0.087(6) Uiso 0.587(18) 1 d PR . . H54A H 0.2163 1.1114 0.5213 0.130 Uiso 0.587(18) 1 calc PR . . H54B H 0.1810 1.2018 0.5078 0.130 Uiso 0.587(18) 1 calc PR . . H54C H 0.2126 1.2135 0.4834 0.130 Uiso 0.587(18) 1 calc PR . . C54' C 0.0529(10) 1.156(2) 0.2744(15) 0.113(11) Uiso 0.413(18) 1 d P . . H54D H 0.0560 1.2314 0.2789 0.170 Uiso 0.413(18) 1 calc PR . . H54E H 0.0264 1.1338 0.2735 0.170 Uiso 0.413(18) 1 calc PR . . H54F H 0.0480 1.1352 0.2343 0.170 Uiso 0.413(18) 1 calc PR . . H48 H 0.1844 1.1552 0.4694 0.136 Uiso 0.41 1 d P . . H52 H 0.0676 1.1440 0.2864 0.136 Uiso 0.59 1 d P . . 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 Br1 0.0290(4) 0.0672(5) 0.0601(5) -0.0122(4) 0.0141(3) 0.0013(3) Br2 0.0273(4) 0.0719(5) 0.0499(4) 0.0158(4) 0.0164(3) 0.0016(3) B1 0.034(4) 0.040(4) 0.032(4) 0.006(3) 0.020(3) 0.004(3) B2 0.031(4) 0.038(4) 0.032(4) -0.004(3) 0.019(3) 0.003(3) C1 0.033(3) 0.033(3) 0.028(3) -0.003(3) 0.015(3) 0.001(3) C2 0.036(3) 0.038(4) 0.035(3) -0.009(3) 0.020(3) -0.010(3) C3 0.050(4) 0.036(4) 0.032(3) -0.004(3) 0.020(3) -0.004(3) C4 0.052(4) 0.037(4) 0.022(3) -0.003(3) 0.013(3) 0.010(3) C5 0.058(5) 0.040(4) 0.031(4) -0.002(3) 0.015(3) 0.018(3) C6 0.064(5) 0.071(6) 0.035(4) -0.002(4) 0.021(4) 0.034(4) C7 0.045(4) 0.075(6) 0.036(4) -0.007(4) 0.020(3) 0.021(4) C8 0.039(4) 0.056(5) 0.034(3) -0.003(3) 0.022(3) 0.014(3) C9 0.034(3) 0.041(4) 0.024(3) -0.002(3) 0.015(3) 0.005(3) C10 0.036(3) 0.032(3) 0.029(3) -0.002(2) 0.020(3) 0.004(3) C11 0.032(3) 0.031(3) 0.031(3) -0.002(2) 0.021(3) 0.003(3) C12 0.029(3) 0.035(3) 0.027(3) 0.001(2) 0.018(3) 0.004(3) C13 0.037(3) 0.052(4) 0.027(3) -0.005(3) 0.017(3) 0.004(3) C14 0.044(4) 0.071(5) 0.024(3) 0.004(3) 0.015(3) 0.011(4) C15 0.046(4) 0.059(5) 0.042(4) 0.018(3) 0.030(4) 0.016(4) C16 0.041(4) 0.048(4) 0.045(4) 0.012(3) 0.030(3) 0.013(3) C17 0.037(3) 0.043(4) 0.037(3) 0.003(3) 0.025(3) 0.003(3) C18 0.044(4) 0.033(4) 0.047(4) -0.001(3) 0.027(3) -0.003(3) C19 0.028(3) 0.046(4) 0.032(3) -0.003(3) 0.013(3) -0.004(3) C20 0.031(3) 0.034(3) 0.030(3) 0.000(3) 0.019(3) 0.002(3) F1 0.049(2) 0.050(2) 0.056(2) -0.0047(19) 0.032(2) -0.0103(19) F2 0.076(3) 0.029(2) 0.063(3) -0.0024(18) 0.035(2) 0.000(2) F3 0.091(3) 0.041(3) 0.061(3) 0.001(2) 0.032(3) 0.025(2) F4 0.094(4) 0.085(4) 0.074(3) 0.010(3) 0.046(3) 0.058(3) F5 0.057(3) 0.107(4) 0.063(3) -0.011(3) 0.039(2) 0.021(3) F6 0.055(2) 0.067(3) 0.065(3) -0.007(2) 0.046(2) 0.003(2) F7 0.058(2) 0.053(3) 0.034(2) -0.0117(18) 0.0184(19) -0.010(2) F8 0.061(3) 0.101(4) 0.023(2) 0.002(2) 0.008(2) 0.011(3) F9 0.055(2) 0.086(3) 0.039(2) 0.026(2) 0.023(2) 0.019(2) F10 0.063(3) 0.046(2) 0.064(3) 0.018(2) 0.040(2) 0.008(2) F11 0.065(3) 0.034(2) 0.064(3) 0.0052(19) 0.028(2) -0.0091(19) F12 0.051(2) 0.046(2) 0.048(2) -0.0110(19) 0.015(2) -0.0144(19) C21 0.028(3) 0.034(3) 0.027(3) 0.000(2) 0.016(3) 0.005(3) C22 0.027(3) 0.048(4) 0.032(3) -0.001(3) 0.015(3) 0.011(3) C23 0.042(4) 0.029(3) 0.042(4) 0.005(3) 0.024(3) 0.011(3) C24 0.040(3) 0.034(3) 0.026(3) 0.001(3) 0.018(3) 0.006(3) C25 0.046(4) 0.037(4) 0.036(3) 0.002(3) 0.024(3) -0.004(3) C26 0.043(4) 0.047(4) 0.033(3) -0.004(3) 0.023(3) -0.013(3) C27 0.036(3) 0.043(4) 0.035(3) -0.006(3) 0.024(3) -0.003(3) C28 0.042(3) 0.030(3) 0.037(3) -0.004(3) 0.027(3) 0.001(3) C29 0.031(3) 0.035(3) 0.015(3) -0.002(2) 0.011(2) 0.006(3) C30 0.029(3) 0.035(3) 0.018(3) -0.001(2) 0.011(2) 0.003(3) C31 0.029(3) 0.025(3) 0.034(3) -0.001(2) 0.022(3) 0.001(2) C32 0.041(4) 0.040(4) 0.038(3) -0.003(3) 0.029(3) 0.001(3) C33 0.038(4) 0.048(4) 0.036(4) -0.007(3) 0.023(3) -0.001(3) C34 0.051(4) 0.060(5) 0.044(4) -0.014(4) 0.030(4) -0.008(4) C35 0.063(5) 0.051(5) 0.065(5) -0.029(4) 0.047(5) -0.027(4) C36 0.069(5) 0.032(4) 0.070(5) -0.015(3) 0.053(5) -0.009(3) C37 0.044(4) 0.034(4) 0.053(4) -0.004(3) 0.036(3) 0.002(3) C38 0.053(4) 0.034(4) 0.048(4) 0.011(3) 0.033(4) 0.012(3) C39 0.030(3) 0.044(4) 0.037(4) 0.007(3) 0.019(3) 0.014(3) C40 0.029(3) 0.035(3) 0.029(3) -0.001(3) 0.017(3) 0.005(3) F13 0.051(2) 0.045(2) 0.080(3) 0.012(2) 0.046(2) 0.0217(19) F14 0.060(3) 0.038(2) 0.071(3) 0.015(2) 0.040(2) 0.0184(19) F15 0.076(3) 0.034(2) 0.070(3) 0.0108(19) 0.049(2) 0.007(2) F16 0.059(2) 0.058(3) 0.055(2) 0.000(2) 0.038(2) -0.013(2) F17 0.050(2) 0.056(3) 0.074(3) -0.008(2) 0.048(2) -0.006(2) F18 0.048(2) 0.040(2) 0.062(2) -0.0026(18) 0.040(2) 0.0036(17) F19 0.052(2) 0.052(2) 0.032(2) -0.0021(18) 0.0163(18) 0.0041(19) F20 0.059(3) 0.083(3) 0.045(2) -0.024(2) 0.022(2) -0.020(2) F21 0.092(3) 0.072(3) 0.079(3) -0.044(3) 0.054(3) -0.047(3) F22 0.095(3) 0.029(2) 0.093(3) -0.014(2) 0.065(3) -0.012(2) F23 0.085(3) 0.033(2) 0.072(3) 0.009(2) 0.044(3) 0.011(2) F24 0.051(2) 0.049(2) 0.039(2) 0.0153(18) 0.0189(19) 0.0171(19) C41 0.072(5) 0.065(5) 0.038(4) -0.003(4) 0.037(4) -0.012(4) C42 0.099(7) 0.058(6) 0.051(5) 0.000(4) 0.041(5) -0.026(5) C43 0.103(8) 0.091(8) 0.070(6) 0.018(5) 0.054(6) 0.040(7) C44 0.075(6) 0.103(8) 0.058(6) 0.007(5) 0.036(5) 0.002(6) C45 0.066(5) 0.074(6) 0.046(4) -0.002(4) 0.033(4) -0.014(5) C46 0.061(5) 0.066(5) 0.039(4) -0.001(4) 0.027(4) -0.011(4) C47 0.087(7) 0.097(7) 0.070(6) -0.010(5) 0.054(6) -0.027(6) C48 0.083(7) 0.093(8) 0.107(8) 0.028(6) 0.074(7) 0.028(6) C49 0.134(10) 0.086(8) 0.126(10) 0.034(7) 0.113(10) 0.040(7) C50 0.146(12) 0.069(7) 0.143(12) 0.020(8) 0.124(11) 0.019(8) C51 0.110(8) 0.077(7) 0.105(8) -0.007(6) 0.086(8) -0.005(6) C52 0.103(9) 0.146(12) 0.119(10) 0.065(9) 0.091(8) 0.051(8) C53 0.083(6) 0.061(6) 0.092(7) 0.003(5) 0.062(6) -0.002(5) 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 Br1 B1 1.902(7) . ? Br2 B2 1.899(7) . ? B1 C1 1.551(9) . ? B1 C40 1.574(9) . ? B2 C20 1.556(9) . ? B2 C21 1.564(9) . ? C1 C10 1.384(8) . ? C1 C2 1.434(9) . ? C2 C3 1.336(9) . ? C2 F1 1.340(7) . ? C3 F2 1.324(8) . ? C3 C4 1.432(10) . ? C4 C9 1.421(9) . ? C4 C5 1.425(9) . ? C5 C6 1.336(12) . ? C5 F3 1.363(9) . ? C6 F4 1.341(8) . ? C6 C7 1.400(12) . ? C7 F5 1.331(9) . ? C7 C8 1.348(9) . ? C8 F6 1.360(8) . ? C8 C9 1.408(9) . ? C9 C10 1.439(8) . ? C10 C11 1.497(8) . ? C11 C20 1.404(8) . ? C11 C12 1.429(8) . ? C12 C13 1.422(8) . ? C12 C17 1.431(9) . ? C13 F7 1.338(8) . ? C13 C14 1.350(9) . ? C14 F8 1.347(8) . ? C14 C15 1.400(11) . ? C15 C16 1.335(10) . ? C15 F9 1.351(7) . ? C16 F10 1.340(8) . ? C16 C17 1.417(9) . ? C17 C18 1.417(9) . ? C18 C19 1.339(9) . ? C18 F11 1.344(7) . ? C19 F12 1.357(7) . ? C19 C20 1.405(9) . ? C21 C30 1.398(8) . ? C21 C22 1.400(9) . ? C22 C23 1.355(9) . ? C22 F13 1.358(7) . ? C23 F14 1.333(7) . ? C23 C24 1.392(9) . ? C24 C25 1.416(9) . ? C24 C29 1.440(8) . ? C25 F15 1.341(7) . ? C25 C26 1.350(9) . ? C26 F16 1.338(7) . ? C26 C27 1.398(9) . ? C27 F17 1.326(7) . ? C27 C28 1.346(9) . ? C28 F18 1.352(7) . ? C28 C29 1.418(8) . ? C29 C30 1.426(8) . ? C30 C31 1.503(8) . ? C31 C40 1.400(8) . ? C31 C32 1.436(8) . ? C32 C33 1.424(9) . ? C32 C37 1.426(9) . ? C33 F19 1.341(8) . ? C33 C34 1.355(9) . ? C34 F20 1.349(8) . ? C34 C35 1.383(11) . ? C35 F21 1.345(8) . ? C35 C36 1.346(11) . ? C36 F22 1.333(8) . ? C36 C37 1.428(9) . ? C37 C38 1.406(9) . ? C38 F23 1.337(7) . ? C38 C39 1.371(9) . ? C39 F24 1.355(7) . ? C39 C40 1.395(9) . ? C41 C46 1.377(11) . ? C41 C42 1.414(12) . ? C41 C47 1.471(12) . ? C42 C43 1.364(14) . ? C43 C44 1.389(15) . ? C44 C45 1.329(13) . ? C45 C46 1.365(11) . ? C48 C53 1.314(12) . ? C48 C49 1.379(15) . ? C48 C54 1.398(14) . ? C49 C50 1.289(16) . ? C50 C51 1.342(16) . ? C51 C52 1.394(16) . ? C52 C54' 1.36(3) . ? C52 C53 1.458(16) . ? 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 C1 B1 C40 123.0(5) . . ? C1 B1 Br1 118.3(5) . . ? C40 B1 Br1 118.8(5) . . ? C20 B2 C21 123.7(5) . . ? C20 B2 Br2 118.3(5) . . ? C21 B2 Br2 117.9(5) . . ? C10 C1 C2 117.2(5) . . ? C10 C1 B1 122.4(5) . . ? C2 C1 B1 120.4(6) . . ? C3 C2 F1 117.3(6) . . ? C3 C2 C1 123.0(6) . . ? F1 C2 C1 119.5(5) . . ? F2 C3 C2 120.0(6) . . ? F2 C3 C4 119.1(6) . . ? C2 C3 C4 120.9(6) . . ? C9 C4 C5 118.3(7) . . ? C9 C4 C3 118.3(6) . . ? C5 C4 C3 123.4(7) . . ? C6 C5 F3 119.1(7) . . ? C6 C5 C4 122.1(7) . . ? F3 C5 C4 118.8(7) . . ? C5 C6 F4 121.1(9) . . ? C5 C6 C7 120.0(7) . . ? F4 C6 C7 118.9(8) . . ? F5 C7 C8 122.3(8) . . ? F5 C7 C6 118.4(7) . . ? C8 C7 C6 119.3(7) . . ? C7 C8 F6 116.6(7) . . ? C7 C8 C9 123.6(7) . . ? F6 C8 C9 119.8(5) . . ? C8 C9 C4 116.6(6) . . ? C8 C9 C10 124.4(6) . . ? C4 C9 C10 119.0(6) . . ? C1 C10 C9 121.6(6) . . ? C1 C10 C11 117.7(5) . . ? C9 C10 C11 120.4(5) . . ? C20 C11 C12 121.2(5) . . ? C20 C11 C10 117.5(5) . . ? C12 C11 C10 121.2(5) . . ? C13 C12 C11 123.9(6) . . ? C13 C12 C17 116.4(5) . . ? C11 C12 C17 119.6(5) . . ? F7 C13 C14 117.5(6) . . ? F7 C13 C12 120.4(5) . . ? C14 C13 C12 122.1(7) . . ? F8 C14 C13 120.6(7) . . ? F8 C14 C15 119.4(6) . . ? C13 C14 C15 120.0(6) . . ? C16 C15 F9 120.7(7) . . ? C16 C15 C14 121.3(6) . . ? F9 C15 C14 118.0(6) . . ? C15 C16 F10 118.8(6) . . ? C15 C16 C17 120.4(6) . . ? F10 C16 C17 120.8(6) . . ? C18 C17 C16 122.9(6) . . ? C18 C17 C12 117.4(5) . . ? C16 C17 C12 119.7(6) . . ? C19 C18 F11 119.9(6) . . ? C19 C18 C17 120.9(6) . . ? F11 C18 C17 119.2(6) . . ? C18 C19 F12 116.6(6) . . ? C18 C19 C20 124.6(6) . . ? F12 C19 C20 118.7(5) . . ? C11 C20 C19 116.2(5) . . ? C11 C20 B2 121.7(5) . . ? C19 C20 B2 122.0(5) . . ? C30 C21 C22 116.1(5) . . ? C30 C21 B2 122.1(5) . . ? C22 C21 B2 121.6(5) . . ? C23 C22 F13 116.7(6) . . ? C23 C22 C21 124.6(5) . . ? F13 C22 C21 118.5(6) . . ? F14 C23 C22 118.5(6) . . ? F14 C23 C24 121.1(6) . . ? C22 C23 C24 120.4(6) . . ? C23 C24 C25 123.0(6) . . ? C23 C24 C29 118.2(6) . . ? C25 C24 C29 118.9(6) . . ? F15 C25 C26 118.7(6) . . ? F15 C25 C24 119.9(6) . . ? C26 C25 C24 121.5(6) . . ? F16 C26 C25 120.6(6) . . ? F16 C26 C27 119.1(6) . . ? C25 C26 C27 120.3(6) . . ? F17 C27 C28 121.7(6) . . ? F17 C27 C26 118.3(6) . . ? C28 C27 C26 119.9(6) . . ? C27 C28 F18 117.8(5) . . ? C27 C28 C29 123.1(6) . . ? F18 C28 C29 119.1(5) . . ? C28 C29 C30 124.8(5) . . ? C28 C29 C24 116.2(5) . . ? C30 C29 C24 118.9(5) . . ? C21 C30 C29 121.5(5) . . ? C21 C30 C31 117.2(5) . . ? C29 C30 C31 121.3(5) . . ? C40 C31 C32 121.2(5) . . ? C40 C31 C30 117.7(5) . . ? C32 C31 C30 120.9(5) . . ? C33 C32 C37 116.9(6) . . ? C33 C32 C31 123.5(6) . . ? C37 C32 C31 119.6(6) . . ? F19 C33 C34 118.0(6) . . ? F19 C33 C32 120.3(6) . . ? C34 C33 C32 121.7(7) . . ? F20 C34 C33 119.5(7) . . ? F20 C34 C35 119.7(6) . . ? C33 C34 C35 120.8(7) . . ? F21 C35 C36 120.6(7) . . ? F21 C35 C34 118.9(7) . . ? C36 C35 C34 120.6(6) . . ? F22 C36 C35 119.3(6) . . ? F22 C36 C37 119.7(7) . . ? C35 C36 C37 121.0(7) . . ? C38 C37 C32 117.8(6) . . ? C38 C37 C36 123.3(6) . . ? C32 C37 C36 118.9(6) . . ? F23 C38 C39 119.1(6) . . ? F23 C38 C37 120.1(6) . . ? C39 C38 C37 120.7(6) . . ? F24 C39 C38 116.4(6) . . ? F24 C39 C40 119.7(6) . . ? C38 C39 C40 123.8(6) . . ? C39 C40 C31 116.8(5) . . ? C39 C40 B1 121.9(5) . . ? C31 C40 B1 121.1(5) . . ? C46 C41 C42 115.2(8) . . ? C46 C41 C47 123.3(8) . . ? C42 C41 C47 121.5(8) . . ? C43 C42 C41 121.9(9) . . ? C42 C43 C44 120.0(10) . . ? C45 C44 C43 118.3(10) . . ? C44 C45 C46 122.6(9) . . ? C45 C46 C41 121.8(8) . . ? C53 C48 C49 122.8(12) . . ? C53 C48 C54 122.9(10) . . ? C49 C48 C54 114.2(10) . . ? C50 C49 C48 120.4(12) . . ? C49 C50 C51 122.7(12) . . ? C50 C51 C52 118.9(12) . . ? C54' C52 C51 119.1(19) . . ? C54' C52 C53 121.2(18) . . ? C51 C52 C53 118.7(10) . . ? C48 C53 C52 116.5(9) . . ? 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 C40 B1 C1 C10 47.3(9) . . . . ? Br1 B1 C1 C10 -131.7(5) . . . . ? C40 B1 C1 C2 -130.8(6) . . . . ? Br1 B1 C1 C2 50.2(7) . . . . ? C10 C1 C2 C3 -2.6(9) . . . . ? B1 C1 C2 C3 175.6(6) . . . . ? C10 C1 C2 F1 -177.2(5) . . . . ? B1 C1 C2 F1 1.0(9) . . . . ? F1 C2 C3 F2 -0.6(9) . . . . ? C1 C2 C3 F2 -175.3(6) . . . . ? F1 C2 C3 C4 176.6(5) . . . . ? C1 C2 C3 C4 1.9(10) . . . . ? F2 C3 C4 C9 176.6(5) . . . . ? C2 C3 C4 C9 -0.6(9) . . . . ? F2 C3 C4 C5 -2.0(9) . . . . ? C2 C3 C4 C5 -179.2(6) . . . . ? C9 C4 C5 C6 -2.4(9) . . . . ? C3 C4 C5 C6 176.2(6) . . . . ? C9 C4 C5 F3 176.9(5) . . . . ? C3 C4 C5 F3 -4.5(9) . . . . ? F3 C5 C6 F4 2.5(10) . . . . ? C4 C5 C6 F4 -178.2(6) . . . . ? F3 C5 C6 C7 -176.8(6) . . . . ? C4 C5 C6 C7 2.5(11) . . . . ? C5 C6 C7 F5 179.0(6) . . . . ? F4 C6 C7 F5 -0.2(10) . . . . ? C5 C6 C7 C8 0.7(11) . . . . ? F4 C6 C7 C8 -178.6(6) . . . . ? F5 C7 C8 F6 -3.0(9) . . . . ? C6 C7 C8 F6 175.3(6) . . . . ? F5 C7 C8 C9 177.6(6) . . . . ? C6 C7 C8 C9 -4.1(10) . . . . ? C7 C8 C9 C4 4.2(9) . . . . ? F6 C8 C9 C4 -175.2(5) . . . . ? C7 C8 C9 C10 -175.4(6) . . . . ? F6 C8 C9 C10 5.2(9) . . . . ? C5 C4 C9 C8 -0.9(8) . . . . ? C3 C4 C9 C8 -179.5(5) . . . . ? C5 C4 C9 C10 178.7(5) . . . . ? C3 C4 C9 C10 0.1(8) . . . . ? C2 C1 C10 C9 2.0(8) . . . . ? B1 C1 C10 C9 -176.2(5) . . . . ? C2 C1 C10 C11 175.1(5) . . . . ? B1 C1 C10 C11 -3.1(8) . . . . ? C8 C9 C10 C1 178.8(6) . . . . ? C4 C9 C10 C1 -0.8(8) . . . . ? C8 C9 C10 C11 5.8(9) . . . . ? C4 C9 C10 C11 -173.7(5) . . . . ? C1 C10 C11 C20 -96.7(7) . . . . ? C9 C10 C11 C20 76.5(7) . . . . ? C1 C10 C11 C12 80.8(7) . . . . ? C9 C10 C11 C12 -106.0(6) . . . . ? C20 C11 C12 C13 -179.3(5) . . . . ? C10 C11 C12 C13 3.3(9) . . . . ? C20 C11 C12 C17 2.5(8) . . . . ? C10 C11 C12 C17 -174.8(5) . . . . ? C11 C12 C13 F7 5.4(9) . . . . ? C17 C12 C13 F7 -176.4(5) . . . . ? C11 C12 C13 C14 -175.2(6) . . . . ? C17 C12 C13 C14 3.0(9) . . . . ? F7 C13 C14 F8 -2.1(9) . . . . ? C12 C13 C14 F8 178.4(6) . . . . ? F7 C13 C14 C15 178.1(6) . . . . ? C12 C13 C14 C15 -1.3(10) . . . . ? F8 C14 C15 C16 179.7(6) . . . . ? C13 C14 C15 C16 -0.5(10) . . . . ? F8 C14 C15 F9 -0.5(10) . . . . ? C13 C14 C15 F9 179.3(6) . . . . ? F9 C15 C16 F10 2.1(9) . . . . ? C14 C15 C16 F10 -178.1(6) . . . . ? F9 C15 C16 C17 -179.3(5) . . . . ? C14 C15 C16 C17 0.5(10) . . . . ? C15 C16 C17 C18 179.5(6) . . . . ? F10 C16 C17 C18 -1.9(9) . . . . ? C15 C16 C17 C12 1.3(9) . . . . ? F10 C16 C17 C12 179.9(5) . . . . ? C13 C12 C17 C18 178.8(5) . . . . ? C11 C12 C17 C18 -2.9(8) . . . . ? C13 C12 C17 C16 -3.0(8) . . . . ? C11 C12 C17 C16 175.3(5) . . . . ? C16 C17 C18 C19 -176.9(6) . . . . ? C12 C17 C18 C19 1.3(9) . . . . ? C16 C17 C18 F11 1.1(9) . . . . ? C12 C17 C18 F11 179.3(5) . . . . ? F11 C18 C19 F12 -0.9(9) . . . . ? C17 C18 C19 F12 177.1(6) . . . . ? F11 C18 C19 C20 -177.0(6) . . . . ? C17 C18 C19 C20 1.0(10) . . . . ? C12 C11 C20 C19 -0.4(8) . . . . ? C10 C11 C20 C19 177.1(5) . . . . ? C12 C11 C20 B2 -177.1(5) . . . . ? C10 C11 C20 B2 0.4(8) . . . . ? C18 C19 C20 C11 -1.4(9) . . . . ? F12 C19 C20 C11 -177.4(5) . . . . ? C18 C19 C20 B2 175.3(6) . . . . ? F12 C19 C20 B2 -0.7(9) . . . . ? C21 B2 C20 C11 44.9(8) . . . . ? Br2 B2 C20 C11 -134.7(5) . . . . ? C21 B2 C20 C19 -131.6(6) . . . . ? Br2 B2 C20 C19 48.8(7) . . . . ? C20 B2 C21 C30 45.7(8) . . . . ? Br2 B2 C21 C30 -134.7(5) . . . . ? C20 B2 C21 C22 -130.1(6) . . . . ? Br2 B2 C21 C22 49.5(7) . . . . ? C30 C21 C22 C23 -2.1(9) . . . . ? B2 C21 C22 C23 174.0(6) . . . . ? C30 C21 C22 F13 -176.7(5) . . . . ? B2 C21 C22 F13 -0.7(8) . . . . ? F13 C22 C23 F14 -1.9(9) . . . . ? C21 C22 C23 F14 -176.6(6) . . . . ? F13 C22 C23 C24 177.2(5) . . . . ? C21 C22 C23 C24 2.4(10) . . . . ? F14 C23 C24 C25 0.2(10) . . . . ? C22 C23 C24 C25 -178.8(6) . . . . ? F14 C23 C24 C29 -179.6(5) . . . . ? C22 C23 C24 C29 1.4(9) . . . . ? C23 C24 C25 F15 0.5(9) . . . . ? C29 C24 C25 F15 -179.6(5) . . . . ? C23 C24 C25 C26 -179.0(6) . . . . ? C29 C24 C25 C26 0.9(9) . . . . ? F15 C25 C26 F16 2.2(9) . . . . ? C24 C25 C26 F16 -178.3(5) . . . . ? F15 C25 C26 C27 -178.0(6) . . . . ? C24 C25 C26 C27 1.5(9) . . . . ? F16 C26 C27 F17 -2.3(9) . . . . ? C25 C26 C27 F17 177.8(6) . . . . ? F16 C26 C27 C28 177.7(5) . . . . ? C25 C26 C27 C28 -2.1(9) . . . . ? F17 C27 C28 F18 -1.2(9) . . . . ? C26 C27 C28 F18 178.8(5) . . . . ? F17 C27 C28 C29 -179.7(5) . . . . ? C26 C27 C28 C29 0.2(9) . . . . ? C27 C28 C29 C30 -175.3(6) . . . . ? F18 C28 C29 C30 6.2(8) . . . . ? C27 C28 C29 C24 2.1(8) . . . . ? F18 C28 C29 C24 -176.5(5) . . . . ? C23 C24 C29 C28 177.3(5) . . . . ? C25 C24 C29 C28 -2.6(8) . . . . ? C23 C24 C29 C30 -5.2(8) . . . . ? C25 C24 C29 C30 174.9(5) . . . . ? C22 C21 C30 C29 -2.1(8) . . . . ? B2 C21 C30 C29 -178.1(5) . . . . ? C22 C21 C30 C31 175.3(5) . . . . ? B2 C21 C30 C31 -0.7(8) . . . . ? C28 C29 C30 C21 -177.1(5) . . . . ? C24 C29 C30 C21 5.7(8) . . . . ? C28 C29 C30 C31 5.7(8) . . . . ? C24 C29 C30 C31 -171.6(5) . . . . ? C21 C30 C31 C40 -97.9(6) . . . . ? C29 C30 C31 C40 79.5(7) . . . . ? C21 C30 C31 C32 77.0(7) . . . . ? C29 C30 C31 C32 -105.6(6) . . . . ? C40 C31 C32 C33 -179.7(5) . . . . ? C30 C31 C32 C33 5.5(9) . . . . ? C40 C31 C32 C37 1.9(8) . . . . ? C30 C31 C32 C37 -172.9(5) . . . . ? C37 C32 C33 F19 -174.7(5) . . . . ? C31 C32 C33 F19 6.8(9) . . . . ? C37 C32 C33 C34 4.1(9) . . . . ? C31 C32 C33 C34 -174.3(6) . . . . ? F19 C33 C34 F20 -2.3(9) . . . . ? C32 C33 C34 F20 178.9(6) . . . . ? F19 C33 C34 C35 175.5(6) . . . . ? C32 C33 C34 C35 -3.3(10) . . . . ? F20 C34 C35 F21 0.1(10) . . . . ? C33 C34 C35 F21 -177.7(6) . . . . ? F20 C34 C35 C36 177.9(6) . . . . ? C33 C34 C35 C36 0.1(11) . . . . ? F21 C35 C36 F22 -0.8(10) . . . . ? C34 C35 C36 F22 -178.5(6) . . . . ? F21 C35 C36 C37 179.8(6) . . . . ? C34 C35 C36 C37 2.1(11) . . . . ? C33 C32 C37 C38 178.8(6) . . . . ? C31 C32 C37 C38 -2.6(8) . . . . ? C33 C32 C37 C36 -1.9(8) . . . . ? C31 C32 C37 C36 176.6(6) . . . . ? F22 C36 C37 C38 -1.3(10) . . . . ? C35 C36 C37 C38 178.1(7) . . . . ? F22 C36 C37 C32 179.5(6) . . . . ? C35 C36 C37 C32 -1.1(10) . . . . ? C32 C37 C38 F23 178.8(6) . . . . ? C36 C37 C38 F23 -0.4(10) . . . . ? C32 C37 C38 C39 1.6(9) . . . . ? C36 C37 C38 C39 -177.6(6) . . . . ? F23 C38 C39 F24 -0.3(9) . . . . ? C37 C38 C39 F24 177.0(5) . . . . ? F23 C38 C39 C40 -176.9(6) . . . . ? C37 C38 C39 C40 0.4(10) . . . . ? F24 C39 C40 C31 -177.7(5) . . . . ? C38 C39 C40 C31 -1.2(9) . . . . ? F24 C39 C40 B1 -3.2(9) . . . . ? C38 C39 C40 B1 173.3(6) . . . . ? C32 C31 C40 C39 0.1(8) . . . . ? C30 C31 C40 C39 175.0(5) . . . . ? C32 C31 C40 B1 -174.5(5) . . . . ? C30 C31 C40 B1 0.4(8) . . . . ? C1 B1 C40 C39 -129.1(6) . . . . ? Br1 B1 C40 C39 49.9(7) . . . . ? C1 B1 C40 C31 45.1(8) . . . . ? Br1 B1 C40 C31 -135.8(5) . . . . ? C46 C41 C42 C43 2.4(12) . . . . ? C47 C41 C42 C43 -178.3(8) . . . . ? C41 C42 C43 C44 -0.8(14) . . . . ? C42 C43 C44 C45 -1.3(14) . . . . ? C43 C44 C45 C46 1.7(13) . . . . ? C44 C45 C46 C41 0.0(12) . . . . ? C42 C41 C46 C45 -2.1(10) . . . . ? C47 C41 C46 C45 178.6(7) . . . . ? C53 C48 C49 C50 2.8(15) . . . . ? C54 C48 C49 C50 178.3(9) . . . . ? C48 C49 C50 C51 -3.6(17) . . . . ? C49 C50 C51 C52 3.6(16) . . . . ? C50 C51 C52 C54' -170.8(17) . . . . ? C50 C51 C52 C53 -2.8(14) . . . . ? C49 C48 C53 C52 -2.1(14) . . . . ? C54 C48 C53 C52 -177.1(6) . . . . ? C54' C52 C53 C48 169.9(17) . . . . ? C51 C52 C53 C48 2.1(13) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 2.650 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.111 # Attachment 'cmpd6.cif' data_cal0548 _database_code_depnum_ccdc_archive 'CCDC 299725' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (R)-(-)-bis((S)-2acetoxypropionato)- 3,3',4,4',5,5',6,6',7,7',8,8'-dodecafluoro-1,1'-binaphthyl ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H14 F12 O8' _chemical_formula_sum 'C30 H14 F12 O8' _chemical_formula_weight 730.41 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' O O 0.0106 0.0060 '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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1781(12) _cell_length_b 12.7075(15) _cell_length_c 11.4937(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.4442(17) _cell_angle_gamma 90.00 _cell_volume 1466.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4769 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_T_max 0.9498 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11649 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.38 _reflns_number_total 5994 _reflns_number_gt 5341 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0423P)^2^+0.1768P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _chemical_absolute_configuration syn _refine_ls_number_reflns 5994 _refine_ls_number_parameters 453 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 F13 F 0.32689(14) -0.23974(9) 0.15485(12) 0.0508(3) Uani 1 1 d . . . F14 F 0.51280(13) -0.21163(10) 0.01843(11) 0.0497(3) Uani 1 1 d . . . F16 F 0.67940(12) -0.09072(9) -0.05818(10) 0.0422(3) Uani 1 1 d . . . F17 F 0.81499(12) 0.08932(11) -0.04227(11) 0.0465(3) Uani 1 1 d . . . F18 F 0.77446(14) 0.23701(11) 0.11669(13) 0.0564(4) Uani 1 1 d . . . F19 F 0.59486(13) 0.20887(10) 0.25878(11) 0.0494(3) Uani 1 1 d . . . F23 F 0.14207(13) 0.31270(11) 0.29006(12) 0.0555(3) Uani 1 1 d . . . F24 F 0.18449(14) 0.29927(12) 0.52487(12) 0.0592(4) Uani 1 1 d . . . F26 F 0.30811(16) 0.21340(13) 0.71452(11) 0.0649(4) Uani 1 1 d . . . F27 F 0.49136(17) 0.07782(15) 0.81660(10) 0.0741(5) Uani 1 1 d . . . F28 F 0.63683(16) -0.03654(14) 0.68637(12) 0.0711(4) Uani 1 1 d . . . F29 F 0.59549(12) -0.02308(11) 0.45231(10) 0.0493(3) Uani 1 1 d . . . O1 O 0.25993(13) -0.08855(10) 0.29587(11) 0.0342(3) Uani 1 1 d . . . O2 O 0.38429(15) -0.19626(15) 0.42507(15) 0.0579(4) Uani 1 1 d . . . O3 O 0.03850(13) -0.13336(12) 0.36521(12) 0.0411(3) Uani 1 1 d . . . O4 O 0.10478(17) 0.00336(14) 0.48365(14) 0.0561(4) Uani 1 1 d . . . O5 O 0.27587(13) 0.19317(11) 0.15435(11) 0.0345(3) Uani 1 1 d . . . O6 O 0.08233(17) 0.10435(16) 0.13291(13) 0.0612(5) Uani 1 1 d . . . O7 O 0.08706(15) 0.12394(12) -0.11686(12) 0.0456(4) Uani 1 1 d . . . O8 O 0.2598(2) 0.01892(15) -0.04921(16) 0.0680(5) Uani 1 1 d . . . C1 C 0.2788(2) -0.16071(16) 0.38446(17) 0.0377(4) Uani 1 1 d . . . C2 C 0.1487(2) -0.19309(18) 0.42254(18) 0.0426(5) Uani 1 1 d . . . H2 H 0.1562 -0.1850 0.5099 0.051 Uiso 1 1 calc R . . C3 C 0.1205(3) -0.3079(2) 0.3886(3) 0.0626(7) Uani 1 1 d . . . H3A H 0.0374 -0.3301 0.4139 0.075 Uiso 1 1 calc R . . H3B H 0.1940 -0.3520 0.4271 0.075 Uiso 1 1 calc R . . H3C H 0.1120 -0.3155 0.3028 0.075 Uiso 1 1 calc R . . C4 C 0.0271(2) -0.03415(19) 0.40461(18) 0.0439(5) Uani 1 1 d . . . C5 C -0.0908(3) 0.0189(2) 0.3367(2) 0.0580(6) Uani 1 1 d . . . H5A H -0.1005 0.0890 0.3698 0.070 Uiso 1 1 calc R . . H5B H -0.1708 -0.0228 0.3413 0.070 Uiso 1 1 calc R . . H5C H -0.0792 0.0256 0.2540 0.070 Uiso 1 1 calc R . . C6 C 0.1593(2) 0.15652(17) 0.09201(17) 0.0397(5) Uani 1 1 d . . . C7 C 0.1435(2) 0.20122(18) -0.03260(16) 0.0407(5) Uani 1 1 d . . . H7 H 0.2322 0.2241 -0.0502 0.049 Uiso 1 1 calc R . . C8 C 0.0486(2) 0.29372(19) -0.0450(2) 0.0508(5) Uani 1 1 d . . . H8A H 0.0389 0.3216 -0.1255 0.061 Uiso 1 1 calc R . . H8B H 0.0839 0.3488 0.0112 0.061 Uiso 1 1 calc R . . H8C H -0.0385 0.2707 -0.0288 0.061 Uiso 1 1 calc R . . C9 C 0.1600(3) 0.0358(2) -0.11982(19) 0.0534(6) Uani 1 1 d . . . C10 C 0.1025(4) -0.0341(2) -0.2189(2) 0.0834(10) Uani 1 1 d . . . H10A H 0.1485 -0.1021 -0.2109 0.100 Uiso 1 1 calc R . . H10B H 0.1136 -0.0015 -0.2940 0.100 Uiso 1 1 calc R . . H10C H 0.0075 -0.0448 -0.2172 0.100 Uiso 1 1 calc R . . C11 C 0.43321(17) 0.02320(14) 0.24775(14) 0.0281(4) Uani 1 1 d . . . C12 C 0.36728(18) -0.07058(14) 0.23757(15) 0.0310(4) Uani 1 1 d . . . C13 C 0.3964(2) -0.14975(15) 0.16091(17) 0.0362(4) Uani 1 1 d . . . C14 C 0.4897(2) -0.13460(15) 0.09147(16) 0.0345(4) Uani 1 1 d . . . C15 C 0.56102(18) -0.03938(15) 0.09580(14) 0.0290(4) Uani 1 1 d . . . C16 C 0.65720(18) -0.01976(15) 0.02223(14) 0.0313(4) Uani 1 1 d . . . C17 C 0.72612(18) 0.07156(16) 0.02917(16) 0.0340(4) Uani 1 1 d . . . C18 C 0.7034(2) 0.14836(16) 0.11046(17) 0.0375(4) Uani 1 1 d . . . C19 C 0.61121(19) 0.13293(15) 0.18139(16) 0.0330(4) Uani 1 1 d . . . C20 C 0.53459(18) 0.04026(14) 0.17676(14) 0.0280(4) Uani 1 1 d . . . C21 C 0.38650(17) 0.10427(14) 0.32612(14) 0.0283(3) Uani 1 1 d . . . C22 C 0.29760(18) 0.17750(15) 0.27601(15) 0.0315(4) Uani 1 1 d . . . C23 C 0.2310(2) 0.24383(16) 0.34425(18) 0.0383(4) Uani 1 1 d . . . C24 C 0.2534(2) 0.23568(17) 0.46385(18) 0.0393(4) Uani 1 1 d . . . C25 C 0.34656(19) 0.16448(16) 0.52179(16) 0.0344(4) Uani 1 1 d . . . C26 C 0.3744(2) 0.15390(19) 0.64609(18) 0.0449(5) Uani 1 1 d . . . C27 C 0.4668(2) 0.0864(2) 0.69847(17) 0.0498(5) Uani 1 1 d . . . C28 C 0.5412(2) 0.0263(2) 0.63183(18) 0.0484(5) Uani 1 1 d . . . C29 C 0.5169(2) 0.03292(17) 0.51180(17) 0.0378(4) Uani 1 1 d . . . C30 C 0.41717(17) 0.09931(15) 0.45216(15) 0.0304(4) 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 F13 0.0610(8) 0.0369(6) 0.0594(7) -0.0113(6) 0.0243(6) -0.0164(6) F14 0.0610(8) 0.0409(7) 0.0525(7) -0.0180(6) 0.0252(6) -0.0059(6) F16 0.0507(7) 0.0435(6) 0.0359(6) -0.0028(5) 0.0169(5) 0.0086(5) F17 0.0425(6) 0.0536(7) 0.0484(6) 0.0091(6) 0.0224(5) 0.0002(6) F18 0.0599(8) 0.0478(7) 0.0672(8) -0.0072(6) 0.0275(7) -0.0208(6) F19 0.0571(7) 0.0424(7) 0.0529(7) -0.0175(6) 0.0215(6) -0.0152(6) F23 0.0534(7) 0.0515(7) 0.0594(8) 0.0007(6) 0.0029(6) 0.0226(6) F24 0.0611(8) 0.0657(9) 0.0546(7) -0.0179(7) 0.0211(6) 0.0177(7) F26 0.0767(9) 0.0854(11) 0.0363(6) -0.0192(7) 0.0209(6) 0.0050(8) F27 0.0898(11) 0.1067(13) 0.0230(6) 0.0014(7) 0.0014(6) 0.0002(10) F28 0.0754(10) 0.0911(11) 0.0398(7) 0.0134(7) -0.0109(7) 0.0238(9) F29 0.0468(7) 0.0621(8) 0.0374(6) 0.0005(6) 0.0021(5) 0.0186(6) O1 0.0335(7) 0.0350(7) 0.0359(6) 0.0031(5) 0.0111(5) -0.0011(5) O2 0.0435(9) 0.0709(11) 0.0599(10) 0.0262(9) 0.0102(8) 0.0070(8) O3 0.0357(7) 0.0515(8) 0.0375(7) 0.0041(6) 0.0106(6) -0.0055(6) O4 0.0596(10) 0.0608(11) 0.0479(8) -0.0085(8) 0.0085(8) -0.0015(8) O5 0.0361(7) 0.0384(7) 0.0275(6) 0.0059(5) 0.0010(5) -0.0023(6) O6 0.0548(9) 0.0877(13) 0.0392(8) 0.0188(9) 0.0018(7) -0.0297(9) O7 0.0520(9) 0.0500(9) 0.0309(7) 0.0058(6) -0.0049(6) -0.0119(7) O8 0.0784(13) 0.0608(11) 0.0575(10) -0.0009(9) -0.0106(9) 0.0091(10) C1 0.0402(11) 0.0378(10) 0.0358(9) 0.0054(8) 0.0088(8) -0.0006(8) C2 0.0423(11) 0.0505(12) 0.0365(10) 0.0091(9) 0.0107(9) -0.0020(10) C3 0.0622(15) 0.0488(14) 0.0789(17) 0.0131(13) 0.0183(13) -0.0075(12) C4 0.0426(11) 0.0544(13) 0.0385(10) 0.0032(10) 0.0179(9) -0.0001(10) C5 0.0536(14) 0.0716(17) 0.0512(13) 0.0094(12) 0.0160(11) 0.0103(13) C6 0.0412(11) 0.0451(11) 0.0316(9) 0.0050(8) 0.0022(8) -0.0057(9) C7 0.0419(11) 0.0494(12) 0.0296(9) 0.0075(9) 0.0027(8) -0.0116(9) C8 0.0500(13) 0.0539(13) 0.0456(11) 0.0103(10) -0.0006(10) -0.0066(11) C9 0.0740(16) 0.0476(13) 0.0357(10) 0.0077(9) 0.0006(11) -0.0085(12) C10 0.130(3) 0.0531(16) 0.0562(15) -0.0004(13) -0.0158(17) -0.0088(18) C11 0.0298(9) 0.0294(9) 0.0244(7) 0.0000(7) 0.0023(6) 0.0011(7) C12 0.0316(9) 0.0347(10) 0.0278(8) 0.0028(7) 0.0080(7) -0.0004(7) C13 0.0396(10) 0.0299(9) 0.0394(10) -0.0028(8) 0.0071(8) -0.0070(8) C14 0.0394(10) 0.0320(9) 0.0328(9) -0.0056(8) 0.0081(8) 0.0028(8) C15 0.0301(8) 0.0315(9) 0.0244(8) 0.0015(7) 0.0012(7) 0.0033(7) C16 0.0330(9) 0.0366(10) 0.0244(8) 0.0014(7) 0.0046(7) 0.0075(8) C17 0.0292(9) 0.0425(11) 0.0317(8) 0.0079(8) 0.0087(7) 0.0037(8) C18 0.0378(10) 0.0354(10) 0.0398(10) 0.0036(8) 0.0076(8) -0.0067(8) C19 0.0347(10) 0.0323(10) 0.0318(9) -0.0043(7) 0.0045(7) 0.0000(8) C20 0.0289(8) 0.0320(9) 0.0222(7) 0.0021(7) 0.0016(6) 0.0022(7) C21 0.0296(8) 0.0309(9) 0.0250(8) -0.0018(7) 0.0060(7) -0.0033(7) C22 0.0330(9) 0.0352(10) 0.0262(8) -0.0002(7) 0.0043(7) -0.0034(8) C23 0.0355(10) 0.0348(10) 0.0439(10) -0.0016(8) 0.0041(8) 0.0069(8) C24 0.0375(10) 0.0420(11) 0.0408(10) -0.0123(9) 0.0134(9) 0.0009(9) C25 0.0345(10) 0.0390(10) 0.0304(9) -0.0063(8) 0.0072(7) -0.0053(8) C26 0.0476(12) 0.0582(13) 0.0311(9) -0.0129(9) 0.0134(9) -0.0077(10) C27 0.0566(13) 0.0682(15) 0.0230(8) 0.0007(10) 0.0013(9) -0.0065(12) C28 0.0498(12) 0.0601(14) 0.0315(9) 0.0074(10) -0.0046(9) 0.0009(11) C29 0.0369(10) 0.0442(11) 0.0312(9) -0.0007(8) 0.0026(8) 0.0002(9) C30 0.0312(9) 0.0348(9) 0.0250(8) -0.0028(7) 0.0041(7) -0.0053(8) _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 F13 C13 1.340(2) . ? F14 C14 1.335(2) . ? F16 C16 1.337(2) . ? F17 C17 1.337(2) . ? F18 C18 1.334(2) . ? F19 C19 1.341(2) . ? F23 C23 1.337(2) . ? F24 C24 1.341(2) . ? F26 C26 1.349(2) . ? F27 C27 1.344(2) . ? F28 C28 1.333(3) . ? F29 C29 1.339(2) . ? O1 C1 1.360(2) . ? O1 C12 1.391(2) . ? O2 C1 1.187(2) . ? O3 C4 1.351(3) . ? O3 C2 1.423(3) . ? O4 C4 1.201(3) . ? O5 C6 1.364(2) . ? O5 C22 1.394(2) . ? O6 C6 1.181(3) . ? O7 C9 1.347(3) . ? O7 C7 1.432(3) . ? O8 C9 1.211(3) . ? C1 C2 1.518(3) . ? C2 C3 1.526(4) . ? C4 C5 1.483(3) . ? C6 C7 1.525(3) . ? C7 C8 1.513(3) . ? C9 C10 1.487(4) . ? C11 C12 1.363(3) . ? C11 C20 1.433(2) . ? C11 C21 1.496(2) . ? C12 C13 1.401(3) . ? C13 C14 1.351(3) . ? C14 C15 1.407(3) . ? C15 C16 1.417(2) . ? C15 C20 1.430(2) . ? C16 C17 1.352(3) . ? C17 C18 1.396(3) . ? C18 C19 1.355(3) . ? C19 C20 1.409(3) . ? C21 C22 1.358(3) . ? C21 C30 1.432(2) . ? C22 C23 1.400(3) . ? C23 C24 1.360(3) . ? C24 C25 1.398(3) . ? C25 C26 1.417(3) . ? C25 C30 1.425(3) . ? C26 C27 1.340(3) . ? C27 C28 1.391(3) . ? C28 C29 1.364(3) . ? C29 C30 1.408(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C12 116.46(14) . . ? C4 O3 C2 116.54(17) . . ? C6 O5 C22 117.35(14) . . ? C9 O7 C7 115.19(17) . . ? O2 C1 O1 123.93(18) . . ? O2 C1 C2 123.98(18) . . ? O1 C1 C2 112.07(16) . . ? O3 C2 C1 112.36(16) . . ? O3 C2 C3 106.91(19) . . ? C1 C2 C3 108.76(19) . . ? O4 C4 O3 122.8(2) . . ? O4 C4 C5 126.4(2) . . ? O3 C4 C5 110.8(2) . . ? O6 C6 O5 124.01(18) . . ? O6 C6 C7 127.48(18) . . ? O5 C6 C7 108.35(16) . . ? O7 C7 C8 106.87(17) . . ? O7 C7 C6 110.41(17) . . ? C8 C7 C6 110.20(18) . . ? O8 C9 O7 122.4(2) . . ? O8 C9 C10 126.1(3) . . ? O7 C9 C10 111.5(2) . . ? C12 C11 C20 118.27(16) . . ? C12 C11 C21 116.94(15) . . ? C20 C11 C21 124.62(16) . . ? C11 C12 O1 121.10(16) . . ? C11 C12 C13 122.00(16) . . ? O1 C12 C13 116.69(16) . . ? F13 C13 C14 120.48(17) . . ? F13 C13 C12 118.75(17) . . ? C14 C13 C12 120.74(17) . . ? F14 C14 C13 118.69(17) . . ? F14 C14 C15 120.65(16) . . ? C13 C14 C15 120.65(17) . . ? C14 C15 C16 122.19(16) . . ? C14 C15 C20 118.73(16) . . ? C16 C15 C20 119.08(16) . . ? F16 C16 C17 118.36(16) . . ? F16 C16 C15 120.37(17) . . ? C17 C16 C15 121.24(16) . . ? F17 C17 C16 120.37(17) . . ? F17 C17 C18 119.72(17) . . ? C16 C17 C18 119.90(16) . . ? F18 C18 C19 120.84(18) . . ? F18 C18 C17 118.60(17) . . ? C19 C18 C17 120.56(18) . . ? F19 C19 C18 117.94(17) . . ? F19 C19 C20 119.90(16) . . ? C18 C19 C20 122.16(17) . . ? C19 C20 C15 117.01(15) . . ? C19 C20 C11 123.43(16) . . ? C15 C20 C11 119.56(15) . . ? C22 C21 C30 118.58(16) . . ? C22 C21 C11 118.15(15) . . ? C30 C21 C11 122.71(16) . . ? C21 C22 O5 120.55(16) . . ? C21 C22 C23 121.67(16) . . ? O5 C22 C23 117.67(17) . . ? F23 C23 C24 120.58(17) . . ? F23 C23 C22 119.09(17) . . ? C24 C23 C22 120.29(17) . . ? F24 C24 C23 117.89(18) . . ? F24 C24 C25 120.86(17) . . ? C23 C24 C25 121.25(17) . . ? C24 C25 C26 123.35(18) . . ? C24 C25 C30 118.28(16) . . ? C26 C25 C30 118.37(18) . . ? C27 C26 F26 118.55(19) . . ? C27 C26 C25 121.56(19) . . ? F26 C26 C25 119.9(2) . . ? C26 C27 F27 120.4(2) . . ? C26 C27 C28 120.63(18) . . ? F27 C27 C28 118.9(2) . . ? F28 C28 C29 120.7(2) . . ? F28 C28 C27 119.45(18) . . ? C29 C28 C27 119.9(2) . . ? F29 C29 C28 117.33(18) . . ? F29 C29 C30 120.86(16) . . ? C28 C29 C30 121.75(19) . . ? C29 C30 C25 117.66(15) . . ? C29 C30 C21 122.59(17) . . ? C25 C30 C21 119.74(16) . . ? 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 C12 O1 C1 O2 11.5(3) . . . . ? C12 O1 C1 C2 -166.63(16) . . . . ? C4 O3 C2 C1 -76.0(2) . . . . ? C4 O3 C2 C3 164.71(18) . . . . ? O2 C1 C2 O3 176.1(2) . . . . ? O1 C1 C2 O3 -5.7(2) . . . . ? O2 C1 C2 C3 -65.7(3) . . . . ? O1 C1 C2 C3 112.4(2) . . . . ? C2 O3 C4 O4 0.1(3) . . . . ? C2 O3 C4 C5 179.53(17) . . . . ? C22 O5 C6 O6 -7.3(3) . . . . ? C22 O5 C6 C7 168.49(17) . . . . ? C9 O7 C7 C8 178.90(17) . . . . ? C9 O7 C7 C6 -61.2(2) . . . . ? O6 C6 C7 O7 -42.7(3) . . . . ? O5 C6 C7 O7 141.67(17) . . . . ? O6 C6 C7 C8 75.1(3) . . . . ? O5 C6 C7 C8 -100.50(19) . . . . ? C7 O7 C9 O8 6.5(3) . . . . ? C7 O7 C9 C10 -173.2(2) . . . . ? C20 C11 C12 O1 -174.17(15) . . . . ? C21 C11 C12 O1 1.2(2) . . . . ? C20 C11 C12 C13 0.4(3) . . . . ? C21 C11 C12 C13 175.76(17) . . . . ? C1 O1 C12 C11 -112.1(2) . . . . ? C1 O1 C12 C13 73.2(2) . . . . ? C11 C12 C13 F13 -179.54(17) . . . . ? O1 C12 C13 F13 -4.8(3) . . . . ? C11 C12 C13 C14 -1.7(3) . . . . ? O1 C12 C13 C14 173.08(17) . . . . ? F13 C13 C14 F14 -1.1(3) . . . . ? C12 C13 C14 F14 -178.98(18) . . . . ? F13 C13 C14 C15 178.68(17) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? F14 C14 C15 C16 1.4(3) . . . . ? C13 C14 C15 C16 -178.40(18) . . . . ? F14 C14 C15 C20 -178.98(16) . . . . ? C13 C14 C15 C20 1.2(3) . . . . ? C14 C15 C16 F16 2.8(3) . . . . ? C20 C15 C16 F16 -176.80(15) . . . . ? C14 C15 C16 C17 -178.89(17) . . . . ? C20 C15 C16 C17 1.5(2) . . . . ? F16 C16 C17 F17 -0.6(3) . . . . ? C15 C16 C17 F17 -178.96(16) . . . . ? F16 C16 C17 C18 178.68(17) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? F17 C17 C18 F18 -1.8(3) . . . . ? C16 C17 C18 F18 178.93(17) . . . . ? F17 C17 C18 C19 178.22(17) . . . . ? C16 C17 C18 C19 -1.1(3) . . . . ? F18 C18 C19 F19 -0.8(3) . . . . ? C17 C18 C19 F19 179.19(17) . . . . ? F18 C18 C19 C20 179.91(18) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? F19 C19 C20 C15 -177.38(15) . . . . ? C18 C19 C20 C15 1.9(3) . . . . ? F19 C19 C20 C11 2.9(3) . . . . ? C18 C19 C20 C11 -177.80(18) . . . . ? C14 C15 C20 C19 177.84(16) . . . . ? C16 C15 C20 C19 -2.5(2) . . . . ? C14 C15 C20 C11 -2.5(2) . . . . ? C16 C15 C20 C11 177.15(16) . . . . ? C12 C11 C20 C19 -178.63(17) . . . . ? C21 C11 C20 C19 6.3(3) . . . . ? C12 C11 C20 C15 1.7(2) . . . . ? C21 C11 C20 C15 -173.34(16) . . . . ? C12 C11 C21 C22 -94.7(2) . . . . ? C20 C11 C21 C22 80.4(2) . . . . ? C12 C11 C21 C30 76.6(2) . . . . ? C20 C11 C21 C30 -108.3(2) . . . . ? C30 C21 C22 O5 172.77(16) . . . . ? C11 C21 C22 O5 -15.6(2) . . . . ? C30 C21 C22 C23 -3.3(3) . . . . ? C11 C21 C22 C23 168.36(17) . . . . ? C6 O5 C22 C21 106.5(2) . . . . ? C6 O5 C22 C23 -77.3(2) . . . . ? C21 C22 C23 F23 -178.35(18) . . . . ? O5 C22 C23 F23 5.5(3) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? O5 C22 C23 C24 -176.74(18) . . . . ? F23 C23 C24 F24 -0.6(3) . . . . ? C22 C23 C24 F24 -178.33(18) . . . . ? F23 C23 C24 C25 -179.64(18) . . . . ? C22 C23 C24 C25 2.6(3) . . . . ? F24 C24 C25 C26 0.2(3) . . . . ? C23 C24 C25 C26 179.3(2) . . . . ? F24 C24 C25 C30 -179.69(18) . . . . ? C23 C24 C25 C30 -0.7(3) . . . . ? C24 C25 C26 C27 -178.4(2) . . . . ? C30 C25 C26 C27 1.5(3) . . . . ? C24 C25 C26 F26 0.9(3) . . . . ? C30 C25 C26 F26 -179.14(19) . . . . ? F26 C26 C27 F27 0.7(3) . . . . ? C25 C26 C27 F27 -180.0(2) . . . . ? F26 C26 C27 C28 -177.6(2) . . . . ? C25 C26 C27 C28 1.8(4) . . . . ? C26 C27 C28 F28 176.8(2) . . . . ? F27 C27 C28 F28 -1.5(4) . . . . ? C26 C27 C28 C29 -2.4(4) . . . . ? F27 C27 C28 C29 179.3(2) . . . . ? F28 C28 C29 F29 -2.2(3) . . . . ? C27 C28 C29 F29 177.0(2) . . . . ? F28 C28 C29 C30 -179.5(2) . . . . ? C27 C28 C29 C30 -0.2(3) . . . . ? F29 C29 C30 C25 -173.74(18) . . . . ? C28 C29 C30 C25 3.4(3) . . . . ? F29 C29 C30 C21 5.4(3) . . . . ? C28 C29 C30 C21 -177.4(2) . . . . ? C24 C25 C30 C29 175.93(18) . . . . ? C26 C25 C30 C29 -4.0(3) . . . . ? C24 C25 C30 C21 -3.2(3) . . . . ? C26 C25 C30 C21 176.83(18) . . . . ? C22 C21 C30 C29 -173.94(17) . . . . ? C11 C21 C30 C29 14.8(3) . . . . ? C22 C21 C30 C25 5.2(3) . . . . ? C11 C21 C30 C25 -166.09(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.178 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.048