# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_3a'cisMTPA(R) _database_code_depnum_ccdc_archive 'CCDC 871978' #TrackingRef '3acis.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 F6 O6 S' _chemical_formula_sum 'C28 H24 F6 O6 S' _chemical_formula_weight 602.53 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.026(4) _cell_length_b 12.876(4) _cell_length_c 21.444(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2768.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'square prisms' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3593 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3593 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0471P)^2^+0.5601P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_number_reflns 3593 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 S1 S 0.9745(2) 0.40468(14) 0.11655(8) 0.0638(5) Uani 1 1 d . . . C2 C 1.1003(8) 0.4857(5) 0.1396(3) 0.066(2) Uani 1 1 d . . . H2 H 1.1402 0.4836 0.1788 0.079 Uiso 1 1 calc R . . C3 C 1.1346(6) 0.5528(5) 0.0944(3) 0.0534(17) Uani 1 1 d . . . H3 H 1.2004 0.6032 0.0989 0.064 Uiso 1 1 calc R . . C3A C 1.0597(5) 0.5382(4) 0.0393(2) 0.0372(14) Uani 1 1 d . . . C4 C 1.0801(5) 0.5946(4) -0.0209(2) 0.0351(13) Uani 1 1 d . . . H4 H 1.0923 0.6690 -0.0132 0.042 Uiso 1 1 calc R . . C5 C 0.9636(6) 0.5771(4) -0.0647(2) 0.0381(14) Uani 1 1 d . . . H5 H 0.8863 0.6158 -0.0491 0.046 Uiso 1 1 calc R . . C6 C 0.9270(6) 0.4635(4) -0.0694(3) 0.0422(15) Uani 1 1 d . . . H6A H 1.0049 0.4230 -0.0807 0.051 Uiso 1 1 calc R . . H6B H 0.8595 0.4538 -0.1013 0.051 Uiso 1 1 calc R . . C7 C 0.8740(6) 0.4281(5) -0.0065(3) 0.0476(15) Uani 1 1 d . . . H7A H 0.7864 0.4579 0.0006 0.057 Uiso 1 1 calc R . . H7B H 0.8653 0.3530 -0.0062 0.057 Uiso 1 1 calc R . . C7A C 0.9665(6) 0.4612(4) 0.0442(2) 0.0398(14) Uani 1 1 d . . . O41 O 1.1998(3) 0.5506(3) -0.05015(17) 0.0380(9) Uani 1 1 d . . . C41 C 1.3106(6) 0.6078(5) -0.0511(2) 0.0360(13) Uani 1 1 d . . . O42 O 1.3194(4) 0.6959(3) -0.0341(2) 0.0592(12) Uani 1 1 d . . . C42 C 1.4285(5) 0.5413(4) -0.0743(2) 0.0346(13) Uani 1 1 d . . . O43 O 1.3958(4) 0.4819(3) -0.12709(16) 0.0439(10) Uani 1 1 d . . . C43 C 1.3334(7) 0.5327(5) -0.1780(3) 0.066(2) Uani 1 1 d . . . H43A H 1.2546 0.5676 -0.1636 0.098 Uiso 1 1 calc R . . H43B H 1.3096 0.4824 -0.2091 0.098 Uiso 1 1 calc R . . H43C H 1.3939 0.5825 -0.1956 0.098 Uiso 1 1 calc R . . C44 C 1.5481(6) 0.6111(5) -0.0904(3) 0.0463(15) Uani 1 1 d . . . F41 F 1.5187(4) 0.6880(3) -0.12978(18) 0.0690(11) Uani 1 1 d . . . F42 F 1.6439(3) 0.5553(3) -0.11646(18) 0.0643(11) Uani 1 1 d . . . F43 F 1.6008(4) 0.6552(3) -0.03995(19) 0.0671(11) Uani 1 1 d . . . C45 C 1.4706(6) 0.4663(4) -0.0229(2) 0.0368(13) Uani 1 1 d . . . C46 C 1.5166(6) 0.3685(4) -0.0372(3) 0.0445(15) Uani 1 1 d . . . H46 H 1.5166 0.3467 -0.0786 0.053 Uiso 1 1 calc R . . C47 C 1.5627(7) 0.3021(5) 0.0085(4) 0.0613(19) Uani 1 1 d . . . H47 H 1.5949 0.2367 -0.0021 0.074 Uiso 1 1 calc R . . C48 C 1.5605(7) 0.3332(6) 0.0692(4) 0.068(2) Uani 1 1 d . . . H48 H 1.5901 0.2886 0.1004 0.082 Uiso 1 1 calc R . . C49 C 1.5152(8) 0.4294(6) 0.0843(3) 0.071(2) Uani 1 1 d . . . H49 H 1.5148 0.4503 0.1259 0.085 Uiso 1 1 calc R . . C410 C 1.4699(7) 0.4961(5) 0.0391(3) 0.0561(18) Uani 1 1 d . . . H410 H 1.4386 0.5615 0.0502 0.067 Uiso 1 1 calc R . . O51 O 0.9955(4) 0.6139(3) -0.12715(16) 0.0430(10) Uani 1 1 d . . . C51 C 0.9426(5) 0.7042(4) -0.1444(2) 0.0358(13) Uani 1 1 d . . . O52 O 0.8806(5) 0.7601(3) -0.11181(19) 0.0657(14) Uani 1 1 d . . . C52 C 0.9746(6) 0.7267(4) -0.2134(2) 0.0375(14) Uani 1 1 d . . . C53 C 0.8399(6) 0.5800(5) -0.2484(3) 0.0628(19) Uani 1 1 d . . . H53A H 0.7898 0.6012 -0.2125 0.094 Uiso 1 1 calc R . . H53B H 0.8612 0.5075 -0.2451 0.094 Uiso 1 1 calc R . . H53C H 0.7879 0.5916 -0.2854 0.094 Uiso 1 1 calc R . . O53 O 0.9608(4) 0.6393(3) -0.25195(17) 0.0478(11) Uani 1 1 d . . . C54 C 0.8795(7) 0.8124(5) -0.2361(3) 0.0511(16) Uani 1 1 d . . . F51 F 0.9016(4) 0.9036(3) -0.20911(17) 0.0631(10) Uani 1 1 d . . . F52 F 0.7498(4) 0.7915(3) -0.2275(2) 0.0748(12) Uani 1 1 d . . . F53 F 0.8945(4) 0.8275(3) -0.29715(18) 0.0827(14) Uani 1 1 d . . . C55 C 1.1169(6) 0.7651(4) -0.2192(3) 0.0417(15) Uani 1 1 d . . . C56 C 1.1822(6) 0.8121(4) -0.1717(3) 0.0500(16) Uani 1 1 d . . . H56 H 1.1390 0.8201 -0.1336 0.060 Uiso 1 1 calc R . . C57 C 1.3108(7) 0.8483(5) -0.1782(4) 0.070(2) Uani 1 1 d . . . H57 H 1.3542 0.8795 -0.1447 0.084 Uiso 1 1 calc R . . C58 C 1.3740(8) 0.8377(6) -0.2347(5) 0.085(3) Uani 1 1 d . . . H58 H 1.4603 0.8628 -0.2397 0.102 Uiso 1 1 calc R . . C59 C 1.3113(8) 0.7909(6) -0.2834(4) 0.078(2) Uani 1 1 d . . . H59 H 1.3554 0.7838 -0.3213 0.094 Uiso 1 1 calc R . . C510 C 1.1825(7) 0.7537(5) -0.2770(3) 0.0606(19) Uani 1 1 d . . . H510 H 1.1397 0.7217 -0.3103 0.073 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 S1 0.0840(13) 0.0588(11) 0.0487(10) 0.0158(9) 0.0111(10) 0.0073(11) C2 0.083(5) 0.077(5) 0.039(4) -0.002(4) -0.003(4) 0.005(4) C3 0.045(4) 0.069(4) 0.046(4) -0.010(3) -0.001(3) -0.006(4) C3A 0.029(3) 0.047(3) 0.036(3) 0.003(3) 0.008(3) 0.009(3) C4 0.030(3) 0.037(3) 0.038(3) -0.003(3) 0.002(3) 0.003(3) C5 0.036(3) 0.040(3) 0.038(3) 0.007(3) 0.009(3) 0.011(3) C6 0.036(3) 0.045(3) 0.046(3) -0.001(3) -0.010(3) -0.003(3) C7 0.036(3) 0.046(4) 0.061(4) 0.006(3) -0.001(3) -0.007(3) C7A 0.040(3) 0.042(3) 0.038(3) 0.008(3) 0.008(3) 0.010(3) O41 0.0272(19) 0.038(2) 0.049(2) -0.0072(19) 0.0064(18) -0.0034(18) C41 0.033(3) 0.045(3) 0.031(3) 0.000(3) 0.000(3) 0.002(3) O42 0.048(3) 0.039(2) 0.091(3) -0.028(2) 0.007(3) -0.005(2) C42 0.029(3) 0.046(3) 0.028(3) -0.004(3) 0.000(2) -0.002(3) O43 0.043(2) 0.050(2) 0.038(2) -0.014(2) -0.006(2) 0.006(2) C43 0.080(5) 0.078(5) 0.038(4) -0.005(4) -0.017(4) 0.005(4) C44 0.035(3) 0.053(4) 0.051(4) 0.002(3) -0.004(3) -0.002(3) F41 0.053(2) 0.064(2) 0.090(3) 0.037(2) -0.001(2) -0.005(2) F42 0.0377(19) 0.072(2) 0.084(3) 0.003(2) 0.021(2) 0.011(2) F43 0.049(2) 0.067(2) 0.086(3) -0.009(2) -0.009(2) -0.018(2) C45 0.033(3) 0.038(3) 0.038(3) -0.004(3) -0.001(3) 0.005(3) C46 0.047(4) 0.043(3) 0.043(3) 0.000(3) 0.002(3) 0.001(3) C47 0.061(5) 0.038(4) 0.084(5) 0.004(4) -0.007(4) -0.003(4) C48 0.071(5) 0.071(5) 0.063(5) 0.032(4) -0.011(4) -0.005(4) C49 0.086(6) 0.079(5) 0.047(4) 0.001(4) -0.008(4) 0.007(5) C410 0.064(4) 0.063(4) 0.042(4) -0.003(3) -0.009(4) 0.012(4) O51 0.047(2) 0.044(2) 0.039(2) 0.0057(19) 0.005(2) 0.012(2) C51 0.037(3) 0.036(3) 0.034(3) 0.002(3) 0.004(3) 0.004(3) O52 0.105(4) 0.049(3) 0.044(3) 0.000(2) 0.021(3) 0.027(3) C52 0.049(3) 0.032(3) 0.031(3) -0.003(3) 0.008(3) -0.001(3) C53 0.057(4) 0.071(5) 0.061(5) -0.016(4) -0.004(4) -0.017(4) O53 0.055(3) 0.051(2) 0.038(2) -0.0167(19) 0.012(2) -0.008(2) C54 0.059(5) 0.056(4) 0.039(4) 0.008(3) -0.003(4) 0.004(4) F51 0.080(3) 0.041(2) 0.069(2) 0.004(2) 0.000(2) 0.015(2) F52 0.043(2) 0.088(3) 0.093(3) 0.007(3) -0.010(2) 0.013(2) F53 0.101(3) 0.097(3) 0.050(2) 0.015(2) -0.004(2) 0.036(3) C55 0.051(4) 0.029(3) 0.046(4) 0.004(3) 0.005(3) 0.000(3) C56 0.051(4) 0.034(3) 0.066(4) 0.005(3) -0.004(4) -0.004(3) C57 0.058(5) 0.048(4) 0.105(7) 0.012(4) -0.020(5) -0.011(4) C58 0.053(5) 0.062(5) 0.139(9) 0.022(6) 0.015(6) -0.008(4) C59 0.066(5) 0.080(6) 0.090(6) -0.003(5) 0.031(5) -0.008(5) C510 0.061(4) 0.060(4) 0.061(5) 0.000(4) 0.015(4) 0.000(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 S1 C2 1.710(7) . ? S1 C7A 1.716(5) . ? C2 C3 1.343(8) . ? C2 H2 0.9300 . ? C3 C3A 1.413(8) . ? C3 H3 0.9300 . ? C3A C7A 1.367(8) . ? C3A C4 1.494(7) . ? C4 O41 1.469(6) . ? C4 C5 1.516(7) . ? C4 H4 0.9800 . ? C5 O51 1.455(6) . ? C5 C6 1.511(7) . ? C5 H5 0.9800 . ? C6 C7 1.521(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C7A 1.491(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O41 C41 1.333(6) . ? C41 O42 1.194(6) . ? C41 C42 1.543(7) . ? C42 O43 1.404(6) . ? C42 C45 1.525(7) . ? C42 C44 1.538(8) . ? O43 C43 1.417(7) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 F42 1.323(7) . ? C44 F43 1.331(7) . ? C44 F41 1.334(6) . ? C45 C46 1.375(7) . ? C45 C410 1.385(7) . ? C46 C47 1.380(8) . ? C46 H46 0.9300 . ? C47 C48 1.364(9) . ? C47 H47 0.9300 . ? C48 C49 1.359(9) . ? C48 H48 0.9300 . ? C49 C410 1.372(8) . ? C49 H49 0.9300 . ? C410 H410 0.9300 . ? O51 C51 1.330(6) . ? C51 O52 1.181(6) . ? C51 C52 1.541(7) . ? C52 O53 1.403(6) . ? C52 C55 1.515(8) . ? C52 C54 1.538(8) . ? C53 O53 1.434(7) . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 F51 1.327(7) . ? C54 F53 1.333(7) . ? C54 F52 1.340(7) . ? C55 C56 1.352(8) . ? C55 C510 1.411(9) . ? C56 C57 1.378(9) . ? C56 H56 0.9300 . ? C57 C58 1.375(10) . ? C57 H57 0.9300 . ? C58 C59 1.360(11) . ? C58 H58 0.9300 . ? C59 C510 1.384(10) . ? C59 H59 0.9300 . ? C510 H510 0.9300 . ? 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 S1 C7A 92.1(3) . . ? C3 C2 S1 111.9(5) . . ? C3 C2 H2 124.1 . . ? S1 C2 H2 124.1 . . ? C2 C3 C3A 112.5(6) . . ? C2 C3 H3 123.8 . . ? C3A C3 H3 123.8 . . ? C7A C3A C3 113.3(5) . . ? C7A C3A C4 120.8(5) . . ? C3 C3A C4 125.8(5) . . ? O41 C4 C3A 107.1(4) . . ? O41 C4 C5 107.9(4) . . ? C3A C4 C5 111.0(4) . . ? O41 C4 H4 110.3 . . ? C3A C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? O51 C5 C6 107.9(4) . . ? O51 C5 C4 110.7(4) . . ? C6 C5 C4 111.8(5) . . ? O51 C5 H5 108.8 . . ? C6 C5 H5 108.8 . . ? C4 C5 H5 108.8 . . ? C5 C6 C7 108.5(5) . . ? C5 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? C5 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? C7A C7 C6 110.0(5) . . ? C7A C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? C7A C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C3A C7A C7 125.3(5) . . ? C3A C7A S1 110.2(4) . . ? C7 C7A S1 124.5(4) . . ? C41 O41 C4 118.3(4) . . ? O42 C41 O41 125.6(5) . . ? O42 C41 C42 124.7(5) . . ? O41 C41 C42 109.6(5) . . ? O43 C42 C45 107.6(4) . . ? O43 C42 C44 108.6(4) . . ? C45 C42 C44 108.4(4) . . ? O43 C42 C41 112.6(4) . . ? C45 C42 C41 109.3(4) . . ? C44 C42 C41 110.2(5) . . ? C42 O43 C43 118.1(4) . . ? O43 C43 H43A 109.5 . . ? O43 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O43 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? F42 C44 F43 106.6(5) . . ? F42 C44 F41 107.2(5) . . ? F43 C44 F41 106.6(5) . . ? F42 C44 C42 110.1(5) . . ? F43 C44 C42 112.2(5) . . ? F41 C44 C42 113.8(5) . . ? C46 C45 C410 118.0(5) . . ? C46 C45 C42 120.7(5) . . ? C410 C45 C42 121.2(5) . . ? C45 C46 C47 121.4(6) . . ? C45 C46 H46 119.3 . . ? C47 C46 H46 119.3 . . ? C48 C47 C46 119.4(6) . . ? C48 C47 H47 120.3 . . ? C46 C47 H47 120.3 . . ? C49 C48 C47 120.1(7) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C410 120.8(7) . . ? C48 C49 H49 119.6 . . ? C410 C49 H49 119.6 . . ? C49 C410 C45 120.2(6) . . ? C49 C410 H410 119.9 . . ? C45 C410 H410 119.9 . . ? C51 O51 C5 117.0(4) . . ? O52 C51 O51 125.3(5) . . ? O52 C51 C52 124.3(5) . . ? O51 C51 C52 110.4(5) . . ? O53 C52 C55 107.9(5) . . ? O53 C52 C54 109.2(5) . . ? C55 C52 C54 108.9(5) . . ? O53 C52 C51 113.2(4) . . ? C55 C52 C51 109.6(5) . . ? C54 C52 C51 108.0(5) . . ? O53 C53 H53A 109.5 . . ? O53 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? O53 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C52 O53 C53 118.6(4) . . ? F51 C54 F53 106.3(5) . . ? F51 C54 F52 106.3(6) . . ? F53 C54 F52 105.9(6) . . ? F51 C54 C52 113.2(5) . . ? F53 C54 C52 110.2(5) . . ? F52 C54 C52 114.5(6) . . ? C56 C55 C510 118.8(6) . . ? C56 C55 C52 122.7(6) . . ? C510 C55 C52 118.4(6) . . ? C55 C56 C57 121.9(7) . . ? C55 C56 H56 119.0 . . ? C57 C56 H56 119.0 . . ? C58 C57 C56 119.1(8) . . ? C58 C57 H57 120.5 . . ? C56 C57 H57 120.5 . . ? C59 C58 C57 120.5(7) . . ? C59 C58 H58 119.7 . . ? C57 C58 H58 119.7 . . ? C58 C59 C510 120.5(8) . . ? C58 C59 H59 119.7 . . ? C510 C59 H59 119.7 . . ? C59 C510 C55 119.1(7) . . ? C59 C510 H510 120.5 . . ? C55 C510 H510 120.5 . . ? 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 C7A S1 C2 C3 0.1(6) . . . . ? S1 C2 C3 C3A -0.9(7) . . . . ? C2 C3 C3A C7A 1.5(8) . . . . ? C2 C3 C3A C4 -175.2(5) . . . . ? C7A C3A C4 O41 -101.3(5) . . . . ? C3 C3A C4 O41 75.2(7) . . . . ? C7A C3A C4 C5 16.2(7) . . . . ? C3 C3A C4 C5 -167.3(5) . . . . ? O41 C4 C5 O51 -51.4(5) . . . . ? C3A C4 C5 O51 -168.4(4) . . . . ? O41 C4 C5 C6 69.0(6) . . . . ? C3A C4 C5 C6 -48.1(6) . . . . ? O51 C5 C6 C7 -171.8(4) . . . . ? C4 C5 C6 C7 66.2(6) . . . . ? C5 C6 C7 C7A -49.0(6) . . . . ? C3 C3A C7A C7 -179.5(5) . . . . ? C4 C3A C7A C7 -2.6(8) . . . . ? C3 C3A C7A S1 -1.4(6) . . . . ? C4 C3A C7A S1 175.5(4) . . . . ? C6 C7 C7A C3A 19.5(8) . . . . ? C6 C7 C7A S1 -158.4(4) . . . . ? C2 S1 C7A C3A 0.8(5) . . . . ? C2 S1 C7A C7 178.9(5) . . . . ? C3A C4 O41 C41 -107.7(5) . . . . ? C5 C4 O41 C41 132.8(4) . . . . ? C4 O41 C41 O42 -5.9(8) . . . . ? C4 O41 C41 C42 171.2(4) . . . . ? O42 C41 C42 O43 -137.7(6) . . . . ? O41 C41 C42 O43 45.2(6) . . . . ? O42 C41 C42 C45 102.8(7) . . . . ? O41 C41 C42 C45 -74.3(5) . . . . ? O42 C41 C42 C44 -16.2(8) . . . . ? O41 C41 C42 C44 166.7(4) . . . . ? C45 C42 O43 C43 170.1(5) . . . . ? C44 C42 O43 C43 -72.7(6) . . . . ? C41 C42 O43 C43 49.7(6) . . . . ? O43 C42 C44 F42 -49.6(6) . . . . ? C45 C42 C44 F42 67.0(6) . . . . ? C41 C42 C44 F42 -173.4(4) . . . . ? O43 C42 C44 F43 -168.2(5) . . . . ? C45 C42 C44 F43 -51.6(6) . . . . ? C41 C42 C44 F43 68.0(6) . . . . ? O43 C42 C44 F41 70.8(6) . . . . ? C45 C42 C44 F41 -172.6(5) . . . . ? C41 C42 C44 F41 -53.1(6) . . . . ? O43 C42 C45 C46 22.9(7) . . . . ? C44 C42 C45 C46 -94.4(6) . . . . ? C41 C42 C45 C46 145.5(5) . . . . ? O43 C42 C45 C410 -160.2(5) . . . . ? C44 C42 C45 C410 82.5(7) . . . . ? C41 C42 C45 C410 -37.6(7) . . . . ? C410 C45 C46 C47 -1.0(9) . . . . ? C42 C45 C46 C47 176.0(5) . . . . ? C45 C46 C47 C48 1.2(10) . . . . ? C46 C47 C48 C49 -1.0(11) . . . . ? C47 C48 C49 C410 0.6(12) . . . . ? C48 C49 C410 C45 -0.4(11) . . . . ? C46 C45 C410 C49 0.6(10) . . . . ? C42 C45 C410 C49 -176.4(6) . . . . ? C6 C5 O51 C51 134.1(5) . . . . ? C4 C5 O51 C51 -103.2(5) . . . . ? C5 O51 C51 O52 6.1(8) . . . . ? C5 O51 C51 C52 -174.5(5) . . . . ? O52 C51 C52 O53 -138.0(6) . . . . ? O51 C51 C52 O53 42.6(6) . . . . ? O52 C51 C52 C55 101.5(7) . . . . ? O51 C51 C52 C55 -77.9(5) . . . . ? O52 C51 C52 C54 -17.0(8) . . . . ? O51 C51 C52 C54 163.6(5) . . . . ? C55 C52 O53 C53 171.7(5) . . . . ? C54 C52 O53 C53 -70.0(6) . . . . ? C51 C52 O53 C53 50.3(7) . . . . ? O53 C52 C54 F51 -169.3(5) . . . . ? C55 C52 C54 F51 -51.7(7) . . . . ? C51 C52 C54 F51 67.2(7) . . . . ? O53 C52 C54 F53 -50.5(7) . . . . ? C55 C52 C54 F53 67.1(7) . . . . ? C51 C52 C54 F53 -173.9(5) . . . . ? O53 C52 C54 F52 68.7(7) . . . . ? C55 C52 C54 F52 -173.7(6) . . . . ? C51 C52 C54 F52 -54.8(7) . . . . ? O53 C52 C55 C56 -148.6(5) . . . . ? C54 C52 C55 C56 93.0(6) . . . . ? C51 C52 C55 C56 -25.0(7) . . . . ? O53 C52 C55 C510 33.1(7) . . . . ? C54 C52 C55 C510 -85.3(6) . . . . ? C51 C52 C55 C510 156.8(5) . . . . ? C510 C55 C56 C57 -0.5(9) . . . . ? C52 C55 C56 C57 -178.7(5) . . . . ? C55 C56 C57 C58 0.9(10) . . . . ? C56 C57 C58 C59 -0.9(12) . . . . ? C57 C58 C59 C510 0.5(13) . . . . ? C58 C59 C510 C55 0.0(11) . . . . ? C56 C55 C510 C59 0.0(9) . . . . ? C52 C55 C510 C59 178.3(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.247 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.057 data_5acisMTPA(R) _database_code_depnum_ccdc_archive 'CCDC 871979' #TrackingRef '5acis.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 F6 O6 S' _chemical_formula_sum 'C28 H22 F6 O6 S' _chemical_formula_weight 600.52 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.186(3) _cell_length_b 12.692(4) _cell_length_c 10.984(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.75(2) _cell_angle_gamma 90.00 _cell_volume 1417.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3595 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3423 _reflns_number_gt 1474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0344P)^2^+0.0464P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0088(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(17) _refine_ls_number_reflns 3423 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1793 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 S1 S 0.44894(19) -0.30950(18) 0.67214(17) 0.0869(7) Uani 1 1 d . . . C2 C 0.4061(6) -0.2678(6) 0.5175(5) 0.0582(18) Uani 1 1 d . . . H2 H 0.4755 -0.2229 0.4877 0.070 Uiso 1 1 calc R . . C3 C 0.3934(6) -0.3697(5) 0.4426(5) 0.0562(17) Uani 1 1 d . . . H3 H 0.4792 -0.3858 0.4116 0.067 Uiso 1 1 calc R . . C3A C 0.3566(6) -0.4579(6) 0.5246(7) 0.0630(19) Uani 1 1 d . . . C4 C 0.3082(7) -0.5552(7) 0.4872(7) 0.076(2) Uani 1 1 d . . . H4 H 0.2889 -0.5693 0.4048 0.091 Uiso 1 1 calc R . . C5 C 0.2893(8) -0.6305(8) 0.5734(10) 0.101(3) Uani 1 1 d . . . H5 H 0.2551 -0.6959 0.5501 0.121 Uiso 1 1 calc R . . C6 C 0.3208(9) -0.6093(9) 0.6950(12) 0.115(4) Uani 1 1 d . . . H6 H 0.3103 -0.6619 0.7525 0.138 Uiso 1 1 calc R . . C7 C 0.3666(8) -0.5139(9) 0.7327(8) 0.096(3) Uani 1 1 d . . . H7 H 0.3849 -0.5007 0.8153 0.115 Uiso 1 1 calc R . . C7A C 0.3859(7) -0.4363(6) 0.6474(7) 0.072(2) Uani 1 1 d . . . O21 O 0.2827(4) -0.2146(3) 0.5070(4) 0.0540(11) Uani 1 1 d . . . C21 C 0.2865(7) -0.1168(6) 0.5544(6) 0.0583(18) Uani 1 1 d . . . O22 O 0.3819(5) -0.0777(4) 0.6049(4) 0.0796(15) Uani 1 1 d . . . C22 C 0.1533(6) -0.0630(5) 0.5343(6) 0.0621(18) Uani 1 1 d . . . O23 O 0.0461(4) -0.1323(4) 0.5386(4) 0.0693(13) Uani 1 1 d . . . C23 C 0.0377(8) -0.1953(6) 0.6472(7) 0.105(3) Uani 1 1 d . . . H23A H 0.1225 -0.2247 0.6704 0.158 Uiso 1 1 calc R . . H23B H -0.0246 -0.2512 0.6313 0.158 Uiso 1 1 calc R . . H23C H 0.0095 -0.1519 0.7122 0.158 Uiso 1 1 calc R . . C24 C 0.1435(11) 0.0234(8) 0.6294(9) 0.100(3) Uani 1 1 d . . . F21 F 0.0206(6) 0.0638(4) 0.6228(5) 0.134(2) Uani 1 1 d . . . F22 F 0.1674(5) -0.0089(4) 0.7434(4) 0.1202(17) Uani 1 1 d . . . F23 F 0.2238(6) 0.1042(4) 0.6116(5) 0.1213(19) Uani 1 1 d . . . C25 C 0.1413(7) -0.0138(5) 0.4070(6) 0.0542(17) Uani 1 1 d . . . C26 C 0.0162(7) 0.0008(5) 0.3504(7) 0.067(2) Uani 1 1 d . . . H26 H -0.0581 -0.0179 0.3903 0.081 Uiso 1 1 calc R . . C27 C 0.0038(8) 0.0427(6) 0.2366(8) 0.081(2) Uani 1 1 d . . . H27 H -0.0799 0.0521 0.1992 0.097 Uiso 1 1 calc R . . C28 C 0.1108(9) 0.0713(6) 0.1754(8) 0.094(3) Uani 1 1 d . . . H28 H 0.1003 0.0999 0.0975 0.112 Uiso 1 1 calc R . . C29 C 0.2337(8) 0.0571(8) 0.2312(8) 0.108(3) Uani 1 1 d . . . H29 H 0.3073 0.0777 0.1912 0.130 Uiso 1 1 calc R . . C210 C 0.2500(7) 0.0122(6) 0.3471(7) 0.088(3) Uani 1 1 d . . . H210 H 0.3338 0.0002 0.3832 0.106 Uiso 1 1 calc R . . O31 O 0.2967(4) -0.3645(3) 0.3401(4) 0.0528(11) Uani 1 1 d . . . C31 C 0.3338(7) -0.3178(6) 0.2403(6) 0.0623(18) Uani 1 1 d . . . O32 O 0.4313(5) -0.2653(5) 0.2359(4) 0.0964(19) Uani 1 1 d . . . C32 C 0.2382(6) -0.3420(5) 0.1318(5) 0.0534(17) Uani 1 1 d . . . O33 O 0.1052(4) -0.3286(3) 0.1562(4) 0.0628(13) Uani 1 1 d . . . C33 C 0.0722(7) -0.2340(5) 0.2206(6) 0.080(2) Uani 1 1 d . . . H33A H 0.1087 -0.2378 0.3033 0.119 Uiso 1 1 calc R . . H33B H -0.0217 -0.2274 0.2202 0.119 Uiso 1 1 calc R . . H33C H 0.1077 -0.1738 0.1812 0.119 Uiso 1 1 calc R . . C34 C 0.2670(8) -0.2734(6) 0.0227(7) 0.072(2) Uani 1 1 d . . . F31 F 0.2651(5) -0.1710(3) 0.0438(4) 0.0995(15) Uani 1 1 d . . . F32 F 0.1791(4) -0.2921(4) -0.0711(3) 0.1075(16) Uani 1 1 d . . . F33 F 0.3838(5) -0.2956(4) -0.0207(3) 0.1032(15) Uani 1 1 d . . . C35 C 0.2578(7) -0.4590(5) 0.1020(5) 0.0573(18) Uani 1 1 d . . . C36 C 0.3839(8) -0.5007(7) 0.1034(8) 0.089(2) Uani 1 1 d . . . H36 H 0.4566 -0.4582 0.1227 0.107 Uiso 1 1 calc R . . C37 C 0.4002(11) -0.6051(9) 0.0762(9) 0.124(4) Uani 1 1 d . . . H37 H 0.4847 -0.6325 0.0736 0.148 Uiso 1 1 calc R . . C38 C 0.2937(13) -0.6694(8) 0.0528(9) 0.120(4) Uani 1 1 d . . . H38 H 0.3060 -0.7404 0.0360 0.144 Uiso 1 1 calc R . . C39 C 0.1682(11) -0.6292(7) 0.0540(8) 0.102(3) Uani 1 1 d . . . H39 H 0.0952 -0.6726 0.0394 0.122 Uiso 1 1 calc R . . C310 C 0.1530(8) -0.5239(6) 0.0771(6) 0.074(2) Uani 1 1 d . . . H310 H 0.0685 -0.4960 0.0758 0.088 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 S1 0.0863(14) 0.1106(19) 0.0608(12) -0.0052(13) -0.0179(10) 0.0328(14) C2 0.040(4) 0.075(5) 0.058(4) -0.007(4) -0.003(3) 0.007(4) C3 0.050(4) 0.062(4) 0.055(4) 0.005(4) -0.003(3) 0.013(4) C3A 0.046(4) 0.070(5) 0.075(5) 0.014(5) 0.015(4) 0.019(4) C4 0.068(5) 0.073(5) 0.087(6) 0.024(5) 0.011(4) 0.023(5) C5 0.071(6) 0.092(7) 0.142(9) 0.045(8) 0.020(6) 0.032(5) C6 0.085(7) 0.124(10) 0.140(10) 0.084(9) 0.029(7) 0.039(7) C7 0.086(6) 0.125(8) 0.078(6) 0.039(7) 0.011(5) 0.039(7) C7A 0.062(5) 0.092(6) 0.062(5) 0.014(5) -0.003(4) 0.036(5) O21 0.049(3) 0.051(3) 0.061(3) -0.006(2) -0.002(2) 0.005(2) C21 0.057(5) 0.061(5) 0.057(4) 0.003(4) 0.003(4) 0.001(4) O22 0.069(3) 0.087(4) 0.081(4) -0.016(3) -0.006(3) -0.014(3) C22 0.064(5) 0.056(4) 0.067(5) -0.005(4) 0.009(4) -0.001(4) O23 0.062(3) 0.061(3) 0.087(4) 0.019(3) 0.017(2) 0.001(3) C23 0.110(7) 0.102(7) 0.108(7) 0.041(6) 0.033(5) 0.003(6) C24 0.127(9) 0.075(7) 0.101(8) -0.005(6) 0.017(7) 0.027(6) F21 0.151(5) 0.127(4) 0.127(4) -0.042(4) 0.027(4) 0.058(4) F22 0.163(5) 0.130(4) 0.068(3) -0.022(3) 0.013(3) 0.014(4) F23 0.174(5) 0.065(3) 0.123(4) -0.031(3) 0.001(4) -0.012(3) C25 0.058(4) 0.039(4) 0.066(4) 0.000(4) 0.006(4) -0.009(4) C26 0.060(5) 0.060(5) 0.081(6) 0.006(4) 0.006(4) 0.014(4) C27 0.081(6) 0.060(5) 0.099(6) 0.008(5) -0.012(5) 0.012(4) C28 0.107(7) 0.087(6) 0.084(6) 0.033(5) -0.017(6) -0.034(6) C29 0.086(6) 0.138(8) 0.099(7) 0.053(6) -0.007(5) -0.040(6) C210 0.058(5) 0.109(7) 0.096(6) 0.024(5) -0.004(4) -0.031(5) O31 0.049(3) 0.063(3) 0.047(2) 0.002(2) 0.007(2) -0.002(2) C31 0.061(4) 0.063(5) 0.063(5) -0.004(4) 0.003(4) -0.015(4) O32 0.095(4) 0.129(5) 0.064(3) 0.007(3) -0.005(3) -0.057(4) C32 0.062(4) 0.055(5) 0.044(4) -0.001(3) 0.010(3) -0.018(3) O33 0.064(3) 0.060(3) 0.065(3) -0.010(2) 0.002(2) -0.005(3) C33 0.083(5) 0.071(5) 0.085(5) -0.007(5) 0.004(4) 0.017(4) C34 0.096(6) 0.065(6) 0.056(5) 0.002(4) 0.014(4) -0.023(5) F31 0.154(4) 0.060(3) 0.085(3) 0.005(3) 0.008(3) -0.033(3) F32 0.151(4) 0.111(4) 0.056(2) 0.020(3) -0.022(2) -0.038(4) F33 0.125(3) 0.112(4) 0.077(3) 0.011(3) 0.041(3) -0.025(3) C35 0.079(5) 0.053(4) 0.040(4) 0.001(3) 0.002(3) -0.009(4) C36 0.079(6) 0.083(6) 0.107(6) -0.013(5) 0.018(5) 0.019(5) C37 0.125(9) 0.096(9) 0.154(10) -0.014(7) 0.045(8) 0.030(7) C38 0.187(11) 0.057(6) 0.119(8) 0.003(6) 0.041(8) 0.025(8) C39 0.155(9) 0.052(5) 0.096(6) -0.002(5) -0.002(6) -0.021(6) C310 0.093(6) 0.057(5) 0.070(5) -0.004(4) -0.002(4) -0.015(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 S1 C7A 1.748(9) . ? S1 C2 1.806(6) . ? C2 O21 1.425(7) . ? C2 C3 1.533(9) . ? C2 H2 0.9800 . ? C3 O31 1.448(6) . ? C3 C3A 1.501(9) . ? C3 H3 0.9800 . ? C3A C4 1.382(9) . ? C3A C7A 1.390(9) . ? C4 C5 1.368(10) . ? C4 H4 0.9300 . ? C5 C6 1.379(13) . ? C5 H5 0.9300 . ? C6 C7 1.352(13) . ? C6 H6 0.9300 . ? C7 C7A 1.383(11) . ? C7 H7 0.9300 . ? O21 C21 1.346(8) . ? C21 O22 1.195(7) . ? C21 C22 1.522(9) . ? C22 O23 1.405(7) . ? C22 C24 1.522(11) . ? C22 C25 1.529(8) . ? O23 C23 1.444(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 F22 1.324(10) . ? C24 F23 1.335(10) . ? C24 F21 1.350(9) . ? C25 C210 1.365(8) . ? C25 C26 1.393(8) . ? C26 C27 1.356(9) . ? C26 H26 0.9300 . ? C27 C28 1.367(10) . ? C27 H27 0.9300 . ? C28 C29 1.369(10) . ? C28 H28 0.9300 . ? C29 C210 1.395(10) . ? C29 H29 0.9300 . ? C210 H210 0.9300 . ? O31 C31 1.323(7) . ? C31 O32 1.200(7) . ? C31 C32 1.520(8) . ? C32 O33 1.409(7) . ? C32 C34 1.526(8) . ? C32 C35 1.536(9) . ? O33 C33 1.444(7) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 F31 1.320(8) . ? C34 F32 1.340(7) . ? C34 F33 1.340(8) . ? C35 C310 1.363(8) . ? C35 C36 1.388(9) . ? C36 C37 1.370(12) . ? C36 H36 0.9300 . ? C37 C38 1.369(13) . ? C37 H37 0.9300 . ? C38 C39 1.377(13) . ? C38 H38 0.9300 . ? C39 C310 1.370(10) . ? C39 H39 0.9300 . ? C310 H310 0.9300 . ? 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 C7A S1 C2 93.4(4) . . ? O21 C2 C3 108.3(5) . . ? O21 C2 S1 111.8(4) . . ? C3 C2 S1 105.3(4) . . ? O21 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? S1 C2 H2 110.4 . . ? O31 C3 C3A 108.4(5) . . ? O31 C3 C2 114.1(5) . . ? C3A C3 C2 108.9(5) . . ? O31 C3 H3 108.4 . . ? C3A C3 H3 108.4 . . ? C2 C3 H3 108.4 . . ? C4 C3A C7A 121.0(7) . . ? C4 C3A C3 126.0(7) . . ? C7A C3A C3 112.9(7) . . ? C5 C4 C3A 118.8(8) . . ? C5 C4 H4 120.6 . . ? C3A C4 H4 120.6 . . ? C4 C5 C6 120.0(10) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 121.7(10) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C7A 119.4(9) . . ? C6 C7 H7 120.3 . . ? C7A C7 H7 120.3 . . ? C7 C7A C3A 119.1(8) . . ? C7 C7A S1 128.1(7) . . ? C3A C7A S1 112.7(6) . . ? C21 O21 C2 113.8(5) . . ? O22 C21 O21 124.4(6) . . ? O22 C21 C22 124.8(7) . . ? O21 C21 C22 110.8(6) . . ? O23 C22 C21 113.7(6) . . ? O23 C22 C24 110.0(6) . . ? C21 C22 C24 108.7(7) . . ? O23 C22 C25 105.7(5) . . ? C21 C22 C25 109.5(5) . . ? C24 C22 C25 109.2(6) . . ? C22 O23 C23 117.6(5) . . ? O23 C23 H23A 109.5 . . ? O23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? F22 C24 F23 107.5(9) . . ? F22 C24 F21 106.3(8) . . ? F23 C24 F21 106.0(8) . . ? F22 C24 C22 114.2(8) . . ? F23 C24 C22 112.6(8) . . ? F21 C24 C22 109.8(8) . . ? C210 C25 C26 120.0(6) . . ? C210 C25 C22 121.4(6) . . ? C26 C25 C22 118.6(6) . . ? C27 C26 C25 119.4(7) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 121.9(8) . . ? C26 C27 H27 119.1 . . ? C28 C27 H27 119.1 . . ? C27 C28 C29 118.7(8) . . ? C27 C28 H28 120.6 . . ? C29 C28 H28 120.6 . . ? C28 C29 C210 120.8(8) . . ? C28 C29 H29 119.6 . . ? C210 C29 H29 119.6 . . ? C25 C210 C29 119.1(7) . . ? C25 C210 H210 120.4 . . ? C29 C210 H210 120.4 . . ? C31 O31 C3 116.6(5) . . ? O32 C31 O31 124.4(6) . . ? O32 C31 C32 124.8(6) . . ? O31 C31 C32 110.8(6) . . ? O33 C32 C31 113.7(5) . . ? O33 C32 C34 108.5(6) . . ? C31 C32 C34 110.8(5) . . ? O33 C32 C35 107.3(5) . . ? C31 C32 C35 106.1(6) . . ? C34 C32 C35 110.5(5) . . ? C32 O33 C33 116.8(5) . . ? O33 C33 H33A 109.5 . . ? O33 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O33 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? F31 C34 F32 107.0(7) . . ? F31 C34 F33 107.0(6) . . ? F32 C34 F33 104.7(6) . . ? F31 C34 C32 114.7(6) . . ? F32 C34 C32 110.5(6) . . ? F33 C34 C32 112.3(6) . . ? C310 C35 C36 118.9(7) . . ? C310 C35 C32 121.1(6) . . ? C36 C35 C32 120.0(7) . . ? C37 C36 C35 119.5(9) . . ? C37 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? C38 C37 C36 120.7(10) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C39 120.1(10) . . ? C37 C38 H38 119.9 . . ? C39 C38 H38 119.9 . . ? C310 C39 C38 118.6(9) . . ? C310 C39 H39 120.7 . . ? C38 C39 H39 120.7 . . ? C35 C310 C39 122.1(8) . . ? C35 C310 H310 119.0 . . ? C39 C310 H310 119.0 . . ? 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 C7A S1 C2 O21 95.5(5) . . . . ? C7A S1 C2 C3 -21.9(4) . . . . ? O21 C2 C3 O31 28.2(7) . . . . ? S1 C2 C3 O31 148.0(4) . . . . ? O21 C2 C3 C3A -93.0(5) . . . . ? S1 C2 C3 C3A 26.8(6) . . . . ? O31 C3 C3A C4 40.1(9) . . . . ? C2 C3 C3A C4 164.8(6) . . . . ? O31 C3 C3A C7A -144.8(5) . . . . ? C2 C3 C3A C7A -20.2(7) . . . . ? C7A C3A C4 C5 0.1(10) . . . . ? C3 C3A C4 C5 174.8(6) . . . . ? C3A C4 C5 C6 -1.3(11) . . . . ? C4 C5 C6 C7 2.2(14) . . . . ? C5 C6 C7 C7A -1.8(14) . . . . ? C6 C7 C7A C3A 0.5(12) . . . . ? C6 C7 C7A S1 -177.5(7) . . . . ? C4 C3A C7A C7 0.3(10) . . . . ? C3 C3A C7A C7 -175.0(6) . . . . ? C4 C3A C7A S1 178.7(5) . . . . ? C3 C3A C7A S1 3.3(7) . . . . ? C2 S1 C7A C7 -170.2(7) . . . . ? C2 S1 C7A C3A 11.6(5) . . . . ? C3 C2 O21 C21 -171.0(5) . . . . ? S1 C2 O21 C21 73.4(6) . . . . ? C2 O21 C21 O22 -2.5(9) . . . . ? C2 O21 C21 C22 177.2(5) . . . . ? O22 C21 C22 O23 -146.2(7) . . . . ? O21 C21 C22 O23 34.1(8) . . . . ? O22 C21 C22 C24 -23.4(10) . . . . ? O21 C21 C22 C24 156.9(6) . . . . ? O22 C21 C22 C25 95.8(8) . . . . ? O21 C21 C22 C25 -83.9(7) . . . . ? C21 C22 O23 C23 56.0(7) . . . . ? C24 C22 O23 C23 -66.1(8) . . . . ? C25 C22 O23 C23 176.1(5) . . . . ? O23 C22 C24 F22 71.6(10) . . . . ? C21 C22 C24 F22 -53.4(10) . . . . ? C25 C22 C24 F22 -172.8(7) . . . . ? O23 C22 C24 F23 -165.5(7) . . . . ? C21 C22 C24 F23 69.5(9) . . . . ? C25 C22 C24 F23 -49.9(10) . . . . ? O23 C22 C24 F21 -47.7(9) . . . . ? C21 C22 C24 F21 -172.7(7) . . . . ? C25 C22 C24 F21 67.9(9) . . . . ? O23 C22 C25 C210 -146.3(6) . . . . ? C21 C22 C25 C210 -23.5(9) . . . . ? C24 C22 C25 C210 95.4(8) . . . . ? O23 C22 C25 C26 31.5(8) . . . . ? C21 C22 C25 C26 154.3(6) . . . . ? C24 C22 C25 C26 -86.8(8) . . . . ? C210 C25 C26 C27 -1.0(11) . . . . ? C22 C25 C26 C27 -178.9(6) . . . . ? C25 C26 C27 C28 -0.2(12) . . . . ? C26 C27 C28 C29 0.0(13) . . . . ? C27 C28 C29 C210 1.3(14) . . . . ? C26 C25 C210 C29 2.4(11) . . . . ? C22 C25 C210 C29 -179.8(7) . . . . ? C28 C29 C210 C25 -2.6(14) . . . . ? C3A C3 O31 C31 -158.0(5) . . . . ? C2 C3 O31 C31 80.5(7) . . . . ? C3 O31 C31 O32 -13.1(10) . . . . ? C3 O31 C31 C32 165.6(5) . . . . ? O32 C31 C32 O33 -133.7(7) . . . . ? O31 C31 C32 O33 47.6(7) . . . . ? O32 C31 C32 C34 -11.3(10) . . . . ? O31 C31 C32 C34 170.0(6) . . . . ? O32 C31 C32 C35 108.5(8) . . . . ? O31 C31 C32 C35 -70.1(6) . . . . ? C31 C32 O33 C33 45.3(7) . . . . ? C34 C32 O33 C33 -78.4(6) . . . . ? C35 C32 O33 C33 162.2(5) . . . . ? O33 C32 C34 F31 68.9(7) . . . . ? C31 C32 C34 F31 -56.5(9) . . . . ? C35 C32 C34 F31 -173.7(6) . . . . ? O33 C32 C34 F32 -52.1(8) . . . . ? C31 C32 C34 F32 -177.5(6) . . . . ? C35 C32 C34 F32 65.3(8) . . . . ? O33 C32 C34 F33 -168.6(6) . . . . ? C31 C32 C34 F33 66.0(8) . . . . ? C35 C32 C34 F33 -51.2(8) . . . . ? O33 C32 C35 C310 14.0(8) . . . . ? C31 C32 C35 C310 135.8(6) . . . . ? C34 C32 C35 C310 -104.1(7) . . . . ? O33 C32 C35 C36 -164.2(6) . . . . ? C31 C32 C35 C36 -42.4(8) . . . . ? C34 C32 C35 C36 77.7(8) . . . . ? C310 C35 C36 C37 2.0(12) . . . . ? C32 C35 C36 C37 -179.8(8) . . . . ? C35 C36 C37 C38 -2.8(16) . . . . ? C36 C37 C38 C39 1.3(17) . . . . ? C37 C38 C39 C310 1.0(15) . . . . ? C36 C35 C310 C39 0.3(11) . . . . ? C32 C35 C310 C39 -177.9(7) . . . . ? C38 C39 C310 C35 -1.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.206 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 data_5etransMTPA(S) _database_code_depnum_ccdc_archive 'CCDC 871980' #TrackingRef '5etrans.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 F6 O7' _chemical_formula_sum 'C28 H22 F6 O7' _chemical_formula_weight 584.46 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.783(2) _cell_length_b 16.637(6) _cell_length_c 23.581(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2661.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'square prisms' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.150 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1961 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 55.09 _reflns_number_total 1961 _reflns_number_gt 1364 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.1289P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(6) _refine_ls_number_reflns 1961 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O -0.0472(12) -0.0775(5) 0.7551(3) 0.065(2) Uani 1 1 d . . . C2 C 0.0430(15) -0.0018(6) 0.7476(4) 0.046(2) Uani 1 1 d . . . H2 H -0.0149 0.0278 0.7157 0.055 Uiso 1 1 calc R . . C3 C 0.2627(15) -0.0137(6) 0.7400(3) 0.047(3) Uani 1 1 d . . . H3 H 0.3425 0.0269 0.7595 0.057 Uiso 1 1 calc R . . C3A C 0.287(2) -0.0946(7) 0.7629(4) 0.068(4) Uani 1 1 d . . . C4 C 0.454(2) -0.1391(9) 0.7750(4) 0.077(4) Uani 1 1 d . . . H4 H 0.5797 -0.1188 0.7687 0.092 Uiso 1 1 calc R . . C5 C 0.425(3) -0.2178(10) 0.7977(6) 0.100(5) Uani 1 1 d . . . H5 H 0.5328 -0.2491 0.8079 0.120 Uiso 1 1 calc R . . C6 C 0.234(4) -0.2474(9) 0.8047(6) 0.116(7) Uani 1 1 d . . . H6 H 0.2193 -0.2999 0.8177 0.140 Uiso 1 1 calc R . . C7 C 0.065(2) -0.2036(9) 0.7935(5) 0.089(4) Uani 1 1 d . . . H7 H -0.0613 -0.2231 0.8002 0.106 Uiso 1 1 calc R . . C7A C 0.1024(19) -0.1280(6) 0.7715(4) 0.053(3) Uani 1 1 d . . . O21 O 0.0211(9) 0.0412(4) 0.8001(2) 0.0463(17) Uani 1 1 d . . . C21 C -0.1614(15) 0.0706(6) 0.8094(4) 0.051(3) Uani 1 1 d . . . O22 O -0.2861(12) 0.0759(5) 0.7737(3) 0.076(2) Uani 1 1 d . . . C22 C -0.1816(15) 0.0973(6) 0.8710(4) 0.052(3) Uani 1 1 d . . . O23 O -0.1382(11) 0.0329(5) 0.9077(2) 0.064(2) Uani 1 1 d . . . C23 C -0.234(2) -0.0429(8) 0.8984(5) 0.090(4) Uani 1 1 d . . . H23A H -0.3728 -0.0372 0.9047 0.136 Uiso 1 1 calc R . . H23B H -0.1812 -0.0821 0.9242 0.136 Uiso 1 1 calc R . . H23C H -0.2109 -0.0601 0.8601 0.136 Uiso 1 1 calc R . . C24 C -0.3911(18) 0.1301(11) 0.8817(5) 0.082(4) Uani 1 1 d . . . F21 F -0.4157(10) 0.1469(6) 0.9355(3) 0.119(3) Uani 1 1 d . . . F22 F -0.5279(10) 0.0765(6) 0.8669(3) 0.113(3) Uani 1 1 d . . . F23 F -0.4265(12) 0.1962(6) 0.8521(4) 0.117(3) Uani 1 1 d . . . C25 C -0.0381(14) 0.1653(6) 0.8851(4) 0.050(3) Uani 1 1 d . . . C26 C 0.0351(16) 0.1727(6) 0.9410(4) 0.056(3) Uani 1 1 d . . . H26 H 0.0002 0.1358 0.9688 0.068 Uiso 1 1 calc R . . C27 C 0.1604(19) 0.2366(7) 0.9533(5) 0.068(3) Uani 1 1 d . . . H27 H 0.2093 0.2412 0.9900 0.081 Uiso 1 1 calc R . . C28 C 0.2148(17) 0.2926(7) 0.9144(5) 0.072(3) Uani 1 1 d . . . H28 H 0.2970 0.3351 0.9242 0.086 Uiso 1 1 calc R . . C29 C 0.144(2) 0.2845(7) 0.8596(5) 0.073(3) Uani 1 1 d . . . H29 H 0.1833 0.3211 0.8320 0.088 Uiso 1 1 calc R . . C210 C 0.0171(19) 0.2232(8) 0.8454(4) 0.067(3) Uani 1 1 d . . . H210 H -0.0327 0.2203 0.8087 0.081 Uiso 1 1 calc R . . O31 O 0.3089(11) -0.0210(4) 0.6785(2) 0.0537(18) Uani 1 1 d . . . C31 C 0.3346(16) 0.0469(6) 0.6508(4) 0.049(2) Uani 1 1 d . . . O32 O 0.3179(16) 0.1116(5) 0.6716(3) 0.084(3) Uani 1 1 d . . . C32 C 0.3968(14) 0.0319(5) 0.5877(3) 0.043(2) Uani 1 1 d . . . O33 O 0.3858(10) -0.0496(4) 0.5741(2) 0.0502(17) Uani 1 1 d . . . C33 C 0.1916(18) -0.0834(6) 0.5697(4) 0.067(3) Uani 1 1 d . . . H33A H 0.1085 -0.0606 0.5985 0.101 Uiso 1 1 calc R . . H33B H 0.1987 -0.1406 0.5747 0.101 Uiso 1 1 calc R . . H33C H 0.1379 -0.0715 0.5330 0.101 Uiso 1 1 calc R . . C34 C 0.6168(17) 0.0511(7) 0.5866(4) 0.060(3) Uani 1 1 d . . . F31 F 0.7001(9) 0.0261(4) 0.5385(2) 0.080(2) Uani 1 1 d . . . F32 F 0.7164(9) 0.0125(4) 0.6276(2) 0.083(2) Uani 1 1 d . . . F33 F 0.6542(10) 0.1280(4) 0.5926(3) 0.086(2) Uani 1 1 d . . . C35 C 0.2892(15) 0.0855(6) 0.5453(4) 0.047(2) Uani 1 1 d . . . C36 C 0.1819(18) 0.1534(6) 0.5588(5) 0.066(3) Uani 1 1 d . . . H36 H 0.1682 0.1685 0.5965 0.079 Uiso 1 1 calc R . . C37 C 0.0938(19) 0.1999(8) 0.5164(6) 0.083(4) Uani 1 1 d . . . H37 H 0.0247 0.2463 0.5260 0.099 Uiso 1 1 calc R . . C38 C 0.1094(19) 0.1770(8) 0.4604(5) 0.080(4) Uani 1 1 d . . . H38 H 0.0473 0.2068 0.4322 0.096 Uiso 1 1 calc R . . C39 C 0.217(2) 0.1103(8) 0.4465(5) 0.078(4) Uani 1 1 d . . . H39 H 0.2318 0.0958 0.4086 0.094 Uiso 1 1 calc R . . C310 C 0.3039(17) 0.0639(7) 0.4887(4) 0.062(3) Uani 1 1 d . . . H310 H 0.3730 0.0178 0.4788 0.074 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 O1 0.068(5) 0.064(5) 0.063(4) -0.020(4) -0.007(4) 0.000(4) C2 0.056(6) 0.044(6) 0.038(5) -0.004(4) 0.005(5) 0.007(5) C3 0.057(7) 0.054(6) 0.031(4) -0.012(4) 0.014(4) 0.007(5) C3A 0.103(11) 0.067(8) 0.034(5) -0.011(5) -0.003(6) 0.017(8) C4 0.071(9) 0.110(11) 0.050(6) -0.015(7) -0.013(6) 0.033(9) C5 0.136(15) 0.086(12) 0.078(10) -0.021(8) -0.024(10) 0.044(12) C6 0.21(2) 0.078(10) 0.059(8) 0.008(7) -0.046(12) 0.024(14) C7 0.119(12) 0.095(11) 0.052(7) -0.013(7) -0.004(8) -0.001(10) C7A 0.079(9) 0.044(6) 0.035(5) 0.004(5) 0.004(5) 0.000(6) O21 0.050(4) 0.060(4) 0.029(3) -0.020(3) 0.001(3) 0.010(3) C21 0.050(7) 0.065(7) 0.036(5) -0.013(5) -0.013(5) 0.018(6) O22 0.069(5) 0.118(6) 0.040(4) -0.019(4) -0.015(4) 0.044(5) C22 0.045(6) 0.081(7) 0.030(5) -0.006(5) 0.009(4) 0.011(6) O23 0.072(5) 0.084(5) 0.036(3) -0.003(3) -0.007(3) -0.018(5) C23 0.107(11) 0.103(10) 0.061(7) 0.007(7) -0.029(7) -0.038(9) C24 0.049(8) 0.140(12) 0.056(7) -0.037(8) -0.004(6) 0.025(9) F21 0.061(5) 0.213(9) 0.082(5) -0.071(5) 0.015(4) 0.014(5) F22 0.038(4) 0.203(9) 0.099(5) -0.052(6) -0.001(4) 0.004(5) F23 0.081(6) 0.141(8) 0.129(7) -0.038(6) -0.022(5) 0.063(6) C25 0.036(6) 0.060(7) 0.055(6) -0.012(5) -0.003(5) 0.018(5) C26 0.060(7) 0.068(7) 0.040(5) -0.015(5) 0.004(5) 0.020(6) C27 0.072(8) 0.072(7) 0.060(6) -0.018(6) -0.024(6) 0.004(7) C28 0.062(7) 0.065(7) 0.088(8) -0.010(7) -0.014(7) -0.005(7) C29 0.088(9) 0.059(7) 0.073(7) 0.006(6) -0.014(7) 0.000(8) C210 0.075(8) 0.079(8) 0.048(6) 0.001(6) -0.007(6) 0.024(8) O31 0.073(5) 0.053(4) 0.035(3) -0.010(3) 0.009(3) 0.001(4) C31 0.063(7) 0.047(6) 0.038(5) -0.007(5) 0.000(5) 0.007(6) O32 0.140(8) 0.056(5) 0.056(4) -0.011(4) 0.009(5) -0.010(6) C32 0.047(6) 0.044(6) 0.038(5) -0.004(4) 0.006(4) -0.006(5) O33 0.061(4) 0.047(4) 0.043(3) -0.005(3) 0.008(3) -0.005(4) C33 0.082(9) 0.056(6) 0.064(7) -0.009(5) 0.009(6) -0.011(7) C34 0.070(7) 0.073(8) 0.038(5) -0.002(5) -0.007(6) -0.001(7) F31 0.059(4) 0.125(6) 0.056(3) -0.008(4) 0.018(3) 0.002(4) F32 0.061(4) 0.125(6) 0.063(4) 0.013(4) -0.005(3) 0.005(4) F33 0.076(5) 0.084(5) 0.099(5) -0.010(4) -0.003(4) -0.033(4) C35 0.052(6) 0.049(6) 0.040(5) -0.007(4) -0.003(5) -0.014(5) C36 0.056(7) 0.076(8) 0.065(7) -0.005(6) 0.002(6) 0.013(7) C37 0.071(9) 0.069(8) 0.108(10) 0.002(8) -0.007(8) 0.008(7) C38 0.057(8) 0.104(10) 0.079(9) 0.015(8) -0.021(7) -0.008(8) C39 0.071(9) 0.100(10) 0.064(7) 0.007(7) -0.007(7) -0.016(8) C310 0.061(7) 0.071(8) 0.053(6) 0.004(5) 0.002(6) -0.008(7) _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 C7A 1.373(13) . ? O1 C2 1.412(11) . ? C2 O21 1.438(10) . ? C2 C3 1.514(14) . ? C2 H2 0.9800 . ? C3 C3A 1.460(14) . ? C3 O31 1.488(9) . ? C3 H3 0.9800 . ? C3A C4 1.381(16) . ? C3A C7A 1.387(17) . ? C4 C5 1.43(2) . ? C4 H4 0.9300 . ? C5 C6 1.40(2) . ? C5 H5 0.9300 . ? C6 C7 1.38(2) . ? C6 H6 0.9300 . ? C7 C7A 1.384(16) . ? C7 H7 0.9300 . ? O21 C21 1.349(11) . ? C21 O22 1.198(11) . ? C21 C22 1.524(12) . ? C22 O23 1.409(12) . ? C22 C25 1.529(14) . ? C22 C24 1.543(15) . ? O23 C23 1.434(12) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 F21 1.309(12) . ? C24 F23 1.324(16) . ? C24 F22 1.333(15) . ? C25 C210 1.396(15) . ? C25 C26 1.413(13) . ? C26 C27 1.391(15) . ? C26 H26 0.9300 . ? C27 C28 1.360(15) . ? C27 H27 0.9300 . ? C28 C29 1.383(15) . ? C28 H28 0.9300 . ? C29 C210 1.378(17) . ? C29 H29 0.9300 . ? C210 H210 0.9300 . ? O31 C31 1.318(10) . ? C31 O32 1.187(10) . ? C31 C32 1.567(12) . ? C32 O33 1.395(10) . ? C32 C34 1.526(14) . ? C32 C35 1.526(13) . ? O33 C33 1.436(13) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 F33 1.313(12) . ? C34 F31 1.332(11) . ? C34 F32 1.342(11) . ? C35 C36 1.381(13) . ? C35 C310 1.386(13) . ? C36 C37 1.398(15) . ? C36 H36 0.9300 . ? C37 C38 1.379(17) . ? C37 H37 0.9300 . ? C38 C39 1.368(17) . ? C38 H38 0.9300 . ? C39 C310 1.390(15) . ? C39 H39 0.9300 . ? C310 H310 0.9300 . ? 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 C7A O1 C2 105.1(8) . . ? O1 C2 O21 107.0(7) . . ? O1 C2 C3 108.9(8) . . ? O21 C2 C3 105.6(8) . . ? O1 C2 H2 111.7 . . ? O21 C2 H2 111.7 . . ? C3 C2 H2 111.7 . . ? C3A C3 O31 105.1(7) . . ? C3A C3 C2 100.9(10) . . ? O31 C3 C2 109.5(8) . . ? C3A C3 H3 113.5 . . ? O31 C3 H3 113.5 . . ? C2 C3 H3 113.5 . . ? C4 C3A C7A 119.6(11) . . ? C4 C3A C3 131.7(13) . . ? C7A C3A C3 108.6(11) . . ? C3A C4 C5 117.2(14) . . ? C3A C4 H4 121.4 . . ? C5 C4 H4 121.4 . . ? C6 C5 C4 119.8(15) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 124.0(15) . . ? C7 C6 H6 118.0 . . ? C5 C6 H6 118.0 . . ? C6 C7 C7A 113.5(15) . . ? C6 C7 H7 123.2 . . ? C7A C7 H7 123.2 . . ? O1 C7A C7 121.8(13) . . ? O1 C7A C3A 112.5(9) . . ? C7 C7A C3A 125.7(13) . . ? C21 O21 C2 114.5(7) . . ? O22 C21 O21 124.1(8) . . ? O22 C21 C22 125.9(9) . . ? O21 C21 C22 110.1(8) . . ? O23 C22 C21 110.1(8) . . ? O23 C22 C25 107.2(8) . . ? C21 C22 C25 111.5(8) . . ? O23 C22 C24 111.1(10) . . ? C21 C22 C24 110.0(9) . . ? C25 C22 C24 106.9(9) . . ? C22 O23 C23 118.8(7) . . ? O23 C23 H23A 109.5 . . ? O23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? F21 C24 F23 108.0(13) . . ? F21 C24 F22 107.9(12) . . ? F23 C24 F22 107.0(10) . . ? F21 C24 C22 110.6(10) . . ? F23 C24 C22 112.0(12) . . ? F22 C24 C22 111.3(11) . . ? C210 C25 C26 118.1(10) . . ? C210 C25 C22 122.3(9) . . ? C26 C25 C22 119.5(9) . . ? C27 C26 C25 118.5(10) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C28 C27 C26 123.2(10) . . ? C28 C27 H27 118.4 . . ? C26 C27 H27 118.4 . . ? C27 C28 C29 118.1(11) . . ? C27 C28 H28 121.0 . . ? C29 C28 H28 121.0 . . ? C210 C29 C28 121.1(11) . . ? C210 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C29 C210 C25 121.0(10) . . ? C29 C210 H210 119.5 . . ? C25 C210 H210 119.5 . . ? C31 O31 C3 116.1(7) . . ? O32 C31 O31 124.1(8) . . ? O32 C31 C32 124.2(9) . . ? O31 C31 C32 111.7(8) . . ? O33 C32 C34 104.6(8) . . ? O33 C32 C35 113.1(7) . . ? C34 C32 C35 109.5(8) . . ? O33 C32 C31 111.1(7) . . ? C34 C32 C31 104.3(8) . . ? C35 C32 C31 113.6(7) . . ? C32 O33 C33 116.5(8) . . ? O33 C33 H33A 109.5 . . ? O33 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O33 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? F33 C34 F31 108.3(9) . . ? F33 C34 F32 106.9(9) . . ? F31 C34 F32 104.5(8) . . ? F33 C34 C32 113.0(9) . . ? F31 C34 C32 111.4(8) . . ? F32 C34 C32 112.3(9) . . ? C36 C35 C310 118.1(10) . . ? C36 C35 C32 125.4(8) . . ? C310 C35 C32 116.4(9) . . ? C35 C36 C37 120.9(10) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C38 C37 C36 119.9(12) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C39 C38 C37 119.7(12) . . ? C39 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? C38 C39 C310 120.3(11) . . ? C38 C39 H39 119.9 . . ? C310 C39 H39 119.9 . . ? C35 C310 C39 121.0(11) . . ? C35 C310 H310 119.5 . . ? C39 C310 H310 119.5 . . ? 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 C7A O1 C2 O21 -93.8(8) . . . . ? C7A O1 C2 C3 19.9(9) . . . . ? O1 C2 C3 C3A -18.4(9) . . . . ? O21 C2 C3 C3A 96.1(8) . . . . ? O1 C2 C3 O31 92.0(9) . . . . ? O21 C2 C3 O31 -153.4(6) . . . . ? O31 C3 C3A C4 74.9(13) . . . . ? C2 C3 C3A C4 -171.2(11) . . . . ? O31 C3 C3A C7A -103.8(9) . . . . ? C2 C3 C3A C7A 10.1(10) . . . . ? C7A C3A C4 C5 -1.8(15) . . . . ? C3 C3A C4 C5 179.7(10) . . . . ? C3A C4 C5 C6 2.4(19) . . . . ? C4 C5 C6 C7 -3(2) . . . . ? C5 C6 C7 C7A 3(2) . . . . ? C2 O1 C7A C7 167.1(9) . . . . ? C2 O1 C7A C3A -13.5(10) . . . . ? C6 C7 C7A O1 176.6(10) . . . . ? C6 C7 C7A C3A -2.7(16) . . . . ? C4 C3A C7A O1 -177.3(9) . . . . ? C3 C3A C7A O1 1.6(11) . . . . ? C4 C3A C7A C7 2.1(16) . . . . ? C3 C3A C7A C7 -179.0(9) . . . . ? O1 C2 O21 C21 -75.7(9) . . . . ? C3 C2 O21 C21 168.4(8) . . . . ? C2 O21 C21 O22 -14.5(14) . . . . ? C2 O21 C21 C22 166.9(8) . . . . ? O22 C21 C22 O23 124.9(11) . . . . ? O21 C21 C22 O23 -56.6(11) . . . . ? O22 C21 C22 C25 -116.3(12) . . . . ? O21 C21 C22 C25 62.3(10) . . . . ? O22 C21 C22 C24 2.1(16) . . . . ? O21 C21 C22 C24 -179.4(10) . . . . ? C21 C22 O23 C23 -50.2(12) . . . . ? C25 C22 O23 C23 -171.7(9) . . . . ? C24 C22 O23 C23 71.9(12) . . . . ? O23 C22 C24 F21 52.5(15) . . . . ? C21 C22 C24 F21 174.7(12) . . . . ? C25 C22 C24 F21 -64.2(15) . . . . ? O23 C22 C24 F23 172.9(9) . . . . ? C21 C22 C24 F23 -64.9(13) . . . . ? C25 C22 C24 F23 56.3(11) . . . . ? O23 C22 C24 F22 -67.4(12) . . . . ? C21 C22 C24 F22 54.8(14) . . . . ? C25 C22 C24 F22 176.0(10) . . . . ? O23 C22 C25 C210 153.7(9) . . . . ? C21 C22 C25 C210 33.1(13) . . . . ? C24 C22 C25 C210 -87.0(12) . . . . ? O23 C22 C25 C26 -29.4(11) . . . . ? C21 C22 C25 C26 -150.0(9) . . . . ? C24 C22 C25 C26 89.8(11) . . . . ? C210 C25 C26 C27 -0.9(14) . . . . ? C22 C25 C26 C27 -177.9(9) . . . . ? C25 C26 C27 C28 0.5(16) . . . . ? C26 C27 C28 C29 -1.1(18) . . . . ? C27 C28 C29 C210 2.2(18) . . . . ? C28 C29 C210 C25 -2.7(18) . . . . ? C26 C25 C210 C29 2.0(16) . . . . ? C22 C25 C210 C29 178.9(10) . . . . ? C3A C3 O31 C31 -167.1(10) . . . . ? C2 C3 O31 C31 85.3(11) . . . . ? C3 O31 C31 O32 -2.1(16) . . . . ? C3 O31 C31 C32 176.0(8) . . . . ? O32 C31 C32 O33 -174.4(11) . . . . ? O31 C31 C32 O33 7.5(12) . . . . ? O32 C31 C32 C34 73.5(14) . . . . ? O31 C31 C32 C34 -104.6(10) . . . . ? O32 C31 C32 C35 -45.6(15) . . . . ? O31 C31 C32 C35 136.3(9) . . . . ? C34 C32 O33 C33 -177.4(7) . . . . ? C35 C32 O33 C33 -58.3(10) . . . . ? C31 C32 O33 C33 70.7(10) . . . . ? O33 C32 C34 F33 173.2(7) . . . . ? C35 C32 C34 F33 51.7(10) . . . . ? C31 C32 C34 F33 -70.2(10) . . . . ? O33 C32 C34 F31 51.0(10) . . . . ? C35 C32 C34 F31 -70.5(10) . . . . ? C31 C32 C34 F31 167.7(8) . . . . ? O33 C32 C34 F32 -65.8(10) . . . . ? C35 C32 C34 F32 172.7(8) . . . . ? C31 C32 C34 F32 50.9(11) . . . . ? O33 C32 C35 C36 142.2(10) . . . . ? C34 C32 C35 C36 -101.6(12) . . . . ? C31 C32 C35 C36 14.5(14) . . . . ? O33 C32 C35 C310 -38.6(12) . . . . ? C34 C32 C35 C310 77.6(11) . . . . ? C31 C32 C35 C310 -166.4(9) . . . . ? C310 C35 C36 C37 -1.2(16) . . . . ? C32 C35 C36 C37 178.0(10) . . . . ? C35 C36 C37 C38 1.6(18) . . . . ? C36 C37 C38 C39 -2.2(19) . . . . ? C37 C38 C39 C310 2.4(19) . . . . ? C36 C35 C310 C39 1.4(17) . . . . ? C32 C35 C310 C39 -177.8(10) . . . . ? C38 C39 C310 C35 -2.0(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 55.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.278 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.071