Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J. Percy' 'Patrick J. Crowley' 'John Fawcett' 'Gerry A. Griffith' 'Andrew C. Moralee' 'Jonathan Percy' _publ_contact_author_name 'Prof J Percy' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email JMP29@LE.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Highly-functionalised Difluorinated Cyclohexane Polyols via the Diels-Alder Reaction: Regiochemical Control via the Phenylsulfonyl Group ; data_7c _database_code_depnum_ccdc_archive 'CCDC 272665' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 F2 N O5' _chemical_formula_weight 333.33 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 9.319(2) _cell_length_b 12.579(3) _cell_length_c 27.029(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3168.3(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.119 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21124 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2784 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+1.1017P] 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 2784 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0820 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 1.16676(9) -0.08048(7) 0.30489(3) 0.0348(2) Uani 1 1 d . . . F2 F 1.10091(9) -0.14571(7) 0.37550(3) 0.0363(2) Uani 1 1 d . . . N1 N 0.85459(12) 0.08460(9) 0.45947(4) 0.0250(3) Uani 1 1 d . . . O1 O 1.32661(11) -0.00976(8) 0.41650(3) 0.0279(2) Uani 1 1 d . . . O2 O 1.12844(11) 0.18318(9) 0.30988(4) 0.0334(3) Uani 1 1 d . . . O3 O 0.93163(11) 0.08301(8) 0.32220(4) 0.0299(3) Uani 1 1 d . . . O4 O 1.02919(10) 0.02611(8) 0.41046(3) 0.0251(2) Uani 1 1 d . . . O5 O 0.99915(11) 0.20372(8) 0.41930(4) 0.0286(2) Uani 1 1 d . . . C1 C 1.27618(15) 0.08624(11) 0.39313(5) 0.0253(3) Uani 1 1 d . . . H1 H 1.2690 0.1493 0.4155 0.030 Uiso 1 1 calc R . . C2 C 1.13066(15) 0.04560(11) 0.37232(5) 0.0236(3) Uani 1 1 d . . . C3 C 1.18067(16) -0.06756(11) 0.35488(5) 0.0266(3) Uani 1 1 d . . . C4 C 1.33774(15) -0.07150(12) 0.37201(5) 0.0267(3) Uani 1 1 d . . . H4 H 1.3791 -0.1443 0.3761 0.032 Uiso 1 1 calc R . . C5 C 1.41964(15) 0.00162(12) 0.33748(5) 0.0266(3) Uani 1 1 d . . . C6 C 1.38016(15) 0.09850(12) 0.35064(5) 0.0266(3) Uani 1 1 d . . . H6 H 1.4112 0.1634 0.3362 0.032 Uiso 1 1 calc R . . C7 C 1.51137(17) -0.03707(14) 0.29602(6) 0.0357(4) Uani 1 1 d . . . H7A H 1.5458 0.0237 0.2767 0.054 Uiso 1 1 calc R . . H7B H 1.4551 -0.0842 0.2747 0.054 Uiso 1 1 calc R . . H7C H 1.5936 -0.0762 0.3095 0.054 Uiso 1 1 calc R . . C8 C 1.06571(15) 0.11386(12) 0.33115(5) 0.0249(3) Uani 1 1 d . . . C9 C 0.84796(16) 0.14627(14) 0.28744(6) 0.0346(4) Uani 1 1 d . . . H9A H 0.7963 0.0989 0.2642 0.042 Uiso 1 1 calc R . . H9B H 0.9125 0.1928 0.2680 0.042 Uiso 1 1 calc R . . C10 C 0.74274(18) 0.21250(14) 0.31572(6) 0.0408(4) Uani 1 1 d . . . H10A H 0.6807 0.1661 0.3355 0.061 Uiso 1 1 calc R . . H10B H 0.6839 0.2536 0.2925 0.061 Uiso 1 1 calc R . . H10C H 0.7946 0.2612 0.3376 0.061 Uiso 1 1 calc R . . C11 C 0.96132(15) 0.11382(11) 0.42936(5) 0.0233(3) Uani 1 1 d . . . C12 C 0.80691(16) -0.02662(12) 0.46345(5) 0.0284(3) Uani 1 1 d . . . H12A H 0.7443 -0.0341 0.4928 0.034 Uiso 1 1 calc R . . H12B H 0.8917 -0.0728 0.4684 0.034 Uiso 1 1 calc R . . C13 C 0.72577(18) -0.06371(13) 0.41800(6) 0.0345(4) Uani 1 1 d . . . H13A H 0.6449 -0.0158 0.4118 0.052 Uiso 1 1 calc R . . H13B H 0.6898 -0.1359 0.4235 0.052 Uiso 1 1 calc R . . H13C H 0.7902 -0.0634 0.3894 0.052 Uiso 1 1 calc R . . C14 C 0.77350(16) 0.16559(12) 0.48644(5) 0.0308(4) Uani 1 1 d . . . H14A H 0.8234 0.2347 0.4831 0.037 Uiso 1 1 calc R . . H14B H 0.7721 0.1467 0.5220 0.037 Uiso 1 1 calc R . . C15 C 0.62056(18) 0.17784(15) 0.46847(7) 0.0462(5) Uani 1 1 d . . . H15A H 0.6209 0.1979 0.4334 0.069 Uiso 1 1 calc R . . H15B H 0.5723 0.2332 0.4878 0.069 Uiso 1 1 calc R . . H15C H 0.5695 0.1103 0.4725 0.069 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 F1 0.0356(5) 0.0394(5) 0.0293(5) -0.0103(4) -0.0051(4) 0.0069(4) F2 0.0351(5) 0.0243(5) 0.0495(6) -0.0016(4) 0.0064(4) -0.0029(4) N1 0.0242(6) 0.0265(6) 0.0242(6) -0.0008(5) 0.0027(5) -0.0012(5) O1 0.0287(6) 0.0313(6) 0.0237(5) 0.0014(4) -0.0015(4) 0.0051(4) O2 0.0279(6) 0.0371(6) 0.0352(6) 0.0117(5) 0.0015(5) 0.0008(5) O3 0.0232(5) 0.0360(6) 0.0306(5) 0.0007(5) -0.0040(4) 0.0007(4) O4 0.0244(5) 0.0238(5) 0.0273(5) 0.0012(4) 0.0044(4) 0.0011(4) O5 0.0299(6) 0.0241(6) 0.0317(6) -0.0001(4) 0.0061(4) -0.0021(4) C1 0.0249(7) 0.0255(7) 0.0257(7) 0.0001(6) -0.0015(6) 0.0023(6) C2 0.0217(7) 0.0256(7) 0.0234(7) -0.0005(6) 0.0021(6) 0.0003(6) C3 0.0292(8) 0.0254(7) 0.0252(7) -0.0009(6) 0.0014(6) -0.0003(6) C4 0.0283(8) 0.0266(7) 0.0252(7) -0.0007(6) 0.0000(6) 0.0064(6) C5 0.0207(7) 0.0343(8) 0.0249(7) 0.0017(7) -0.0027(6) 0.0035(6) C6 0.0203(7) 0.0314(8) 0.0282(7) 0.0028(6) -0.0018(6) -0.0008(6) C7 0.0312(8) 0.0429(9) 0.0331(8) 0.0004(7) 0.0047(7) 0.0093(7) C8 0.0230(7) 0.0276(8) 0.0241(7) -0.0042(6) 0.0021(6) 0.0037(6) C9 0.0266(8) 0.0479(10) 0.0292(8) 0.0033(7) -0.0056(6) 0.0052(7) C10 0.0357(9) 0.0428(10) 0.0439(9) -0.0032(8) -0.0022(8) 0.0084(8) C11 0.0231(7) 0.0264(8) 0.0203(7) -0.0015(6) -0.0027(6) 0.0010(6) C12 0.0293(8) 0.0272(8) 0.0288(7) 0.0040(6) 0.0032(6) -0.0025(6) C13 0.0341(9) 0.0306(8) 0.0390(9) 0.0015(7) -0.0019(7) -0.0068(7) C14 0.0341(9) 0.0312(8) 0.0273(7) -0.0036(6) 0.0081(7) -0.0018(7) C15 0.0302(9) 0.0426(10) 0.0659(12) -0.0151(9) 0.0114(9) 0.0022(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 F1 C3 1.3668(17) . ? F2 C3 1.3526(17) . ? N1 C11 1.3367(19) . ? N1 C14 1.4631(18) . ? N1 C12 1.4719(19) . ? O1 C4 1.4353(17) . ? O1 C1 1.4415(17) . ? O2 C8 1.1969(18) . ? O3 C8 1.3305(18) . ? O3 C9 1.4573(18) . ? O4 C11 1.3705(17) . ? O4 C2 1.4202(17) . ? O5 C11 1.2153(17) . ? C1 C6 1.510(2) . ? C1 C2 1.554(2) . ? C2 C8 1.530(2) . ? C2 C3 1.5703(19) . ? C3 C4 1.536(2) . ? C4 C5 1.516(2) . ? C5 C6 1.322(2) . ? C5 C7 1.491(2) . ? C9 C10 1.497(2) . ? C12 C13 1.516(2) . ? C14 C15 1.514(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 C11 N1 C14 119.75(12) . . ? C11 N1 C12 122.04(12) . . ? C14 N1 C12 118.01(11) . . ? C4 O1 C1 96.30(10) . . ? C8 O3 C9 117.41(12) . . ? C11 O4 C2 116.02(11) . . ? O1 C1 C6 102.10(11) . . ? O1 C1 C2 99.64(11) . . ? C6 C1 C2 108.56(11) . . ? O4 C2 C8 111.19(11) . . ? O4 C2 C1 112.03(11) . . ? C8 C2 C1 115.06(12) . . ? O4 C2 C3 105.01(11) . . ? C8 C2 C3 114.05(11) . . ? C1 C2 C3 98.50(11) . . ? F2 C3 F1 105.60(11) . . ? F2 C3 C4 112.08(12) . . ? F1 C3 C4 112.61(12) . . ? F2 C3 C2 111.84(11) . . ? F1 C3 C2 112.11(11) . . ? C4 C3 C2 102.80(11) . . ? O1 C4 C5 102.93(12) . . ? O1 C4 C3 99.57(11) . . ? C5 C4 C3 105.93(11) . . ? C6 C5 C7 131.51(14) . . ? C6 C5 C4 104.69(13) . . ? C7 C5 C4 123.58(14) . . ? C5 C6 C1 106.79(13) . . ? O2 C8 O3 125.72(14) . . ? O2 C8 C2 124.39(13) . . ? O3 C8 C2 109.87(12) . . ? O3 C9 C10 108.98(13) . . ? O5 C11 N1 127.44(13) . . ? O5 C11 O4 122.14(13) . . ? N1 C11 O4 110.42(12) . . ? N1 C12 C13 112.57(12) . . ? N1 C14 C15 113.41(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.266 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.037 #===END data_9a _database_code_depnum_ccdc_archive 'CCDC 272666' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 F2 N O5 S' _chemical_formula_sum 'C18 H19 F2 N O5 S' _chemical_formula_weight 399.40 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' N N 0.0061 0.0033 '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)/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 10.4325(7) _cell_length_b 11.7993(8) _cell_length_c 14.7171(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.0510(10) _cell_angle_gamma 90.00 _cell_volume 1810.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3109 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 26.72 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 999 reflections (SADABS); Rint 0.055 before correction 0.040 after correction. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13859 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3555 _reflns_number_gt 3037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.1006P] 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 3555 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.49415(4) 0.73959(3) 0.10969(3) 0.02456(14) Uani 1 1 d . . . F1 F 0.15888(9) 0.53964(8) 0.22179(7) 0.0309(3) Uani 1 1 d . . . F2 F 0.09288(9) 0.49673(8) 0.08427(7) 0.0328(3) Uani 1 1 d . . . O7 O 0.34316(10) 0.53775(9) 0.02740(7) 0.0232(3) Uani 1 1 d . . . O1 O 0.44571(10) 0.45144(9) 0.24649(7) 0.0249(3) Uani 1 1 d . . . O2 O 0.30533(12) 0.31989(10) 0.29033(8) 0.0306(3) Uani 1 1 d . . . O3 O 0.21684(10) 0.31079(9) 0.10394(8) 0.0250(3) Uani 1 1 d . . . O4 O 0.40403(11) 0.21315(9) 0.11647(8) 0.0271(3) Uani 1 1 d . . . N1 N 0.21720(14) 0.12552(12) 0.07102(10) 0.0315(4) Uani 1 1 d . . . C1 C 0.39785(14) 0.45076(13) 0.08508(10) 0.0206(3) Uani 1 1 d . . . H1 H 0.4498 0.3924 0.0536 0.025 Uiso 1 1 calc R . . C2 C 0.28595(14) 0.40445(13) 0.13858(10) 0.0210(3) Uani 1 1 d . . . C3 C 0.19930(15) 0.51212(14) 0.13790(11) 0.0237(4) Uani 1 1 d . . . C4 C 0.28504(15) 0.60305(13) 0.09700(11) 0.0229(4) Uani 1 1 d . . . H4 H 0.2377 0.6716 0.0741 0.027 Uiso 1 1 calc R . . C5 C 0.39942(14) 0.62952(13) 0.16222(10) 0.0211(3) Uani 1 1 d . . . H5 H 0.3713 0.6522 0.2239 0.025 Uiso 1 1 calc R . . C6 C 0.46909(15) 0.51460(13) 0.16389(10) 0.0209(3) Uani 1 1 d . . . H6 H 0.5628 0.5229 0.1532 0.025 Uiso 1 1 calc R . . C7 C 0.34311(15) 0.38338(13) 0.23364(11) 0.0232(4) Uani 1 1 d . . . C8 C 0.28997(16) 0.21345(14) 0.09783(11) 0.0245(4) Uani 1 1 d . . . C9 C 0.07693(18) 0.13401(16) 0.05784(13) 0.0379(5) Uani 1 1 d . . . H9A H 0.0424 0.1784 0.1085 0.045 Uiso 1 1 calc R . . H9B H 0.0395 0.0570 0.0603 0.045 Uiso 1 1 calc R . . C10 C 0.0354(2) 0.18876(18) -0.03073(15) 0.0504(6) Uani 1 1 d . . . H10A H 0.0683 0.2665 -0.0324 0.076 Uiso 1 1 calc R . . H10B H -0.0585 0.1901 -0.0362 0.076 Uiso 1 1 calc R . . H10C H 0.0694 0.1454 -0.0813 0.076 Uiso 1 1 calc R . . C11 C 0.28146(19) 0.01632(14) 0.05604(13) 0.0338(4) Uani 1 1 d . . . H11A H 0.2265 -0.0454 0.0784 0.041 Uiso 1 1 calc R . . H11B H 0.3631 0.0148 0.0925 0.041 Uiso 1 1 calc R . . C12 C 0.3096(2) -0.00650(17) -0.04186(14) 0.0524(6) Uani 1 1 d . . . H12A H 0.2291 -0.0086 -0.0782 0.079 Uiso 1 1 calc R . . H12B H 0.3536 -0.0795 -0.0466 0.079 Uiso 1 1 calc R . . H12C H 0.3646 0.0538 -0.0646 0.079 Uiso 1 1 calc R . . C13 C 0.61252(16) 0.75933(13) 0.19815(11) 0.0237(4) Uani 1 1 d . . . C14 C 0.58878(18) 0.83338(15) 0.26907(12) 0.0321(4) Uani 1 1 d . . . H14 H 0.5097 0.8732 0.2700 0.038 Uiso 1 1 calc R . . C15 C 0.68064(19) 0.84902(17) 0.33839(13) 0.0387(5) Uani 1 1 d . . . H15 H 0.6642 0.8993 0.3870 0.046 Uiso 1 1 calc R . . C16 C 0.79521(19) 0.79210(17) 0.33702(14) 0.0382(5) Uani 1 1 d . . . H16 H 0.8574 0.8026 0.3850 0.046 Uiso 1 1 calc R . . C17 C 0.82065(18) 0.71964(17) 0.26615(15) 0.0399(5) Uani 1 1 d . . . H17 H 0.9004 0.6809 0.2652 0.048 Uiso 1 1 calc R . . C18 C 0.72992(17) 0.70353(15) 0.19663(13) 0.0320(4) Uani 1 1 d . . . H18 H 0.7478 0.6542 0.1477 0.038 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 0.0304(3) 0.0173(2) 0.0259(2) 0.00188(15) 0.00013(17) -0.00434(16) F1 0.0335(6) 0.0229(5) 0.0370(6) -0.0047(4) 0.0119(4) 0.0001(4) F2 0.0224(5) 0.0282(6) 0.0471(6) -0.0030(5) -0.0075(4) -0.0007(4) O7 0.0295(6) 0.0183(6) 0.0215(6) -0.0003(4) -0.0011(5) 0.0024(5) O1 0.0305(6) 0.0190(6) 0.0248(6) 0.0025(4) -0.0046(5) -0.0054(5) O2 0.0423(8) 0.0218(6) 0.0280(6) 0.0027(5) 0.0066(5) -0.0050(5) O3 0.0236(6) 0.0162(6) 0.0348(7) -0.0063(5) -0.0025(5) -0.0033(4) O4 0.0267(7) 0.0206(6) 0.0340(7) 0.0001(5) -0.0006(5) -0.0008(5) N1 0.0346(8) 0.0175(7) 0.0417(9) -0.0055(6) -0.0070(7) -0.0034(6) C1 0.0231(8) 0.0149(7) 0.0236(8) 0.0006(6) -0.0004(6) 0.0007(6) C2 0.0220(8) 0.0144(8) 0.0263(9) -0.0035(6) -0.0010(6) -0.0026(6) C3 0.0205(8) 0.0219(8) 0.0285(9) -0.0030(7) 0.0001(7) 0.0002(7) C4 0.0247(8) 0.0165(8) 0.0272(9) -0.0011(6) -0.0010(7) 0.0022(6) C5 0.0239(8) 0.0161(8) 0.0233(8) 0.0001(6) 0.0007(6) -0.0030(6) C6 0.0233(8) 0.0162(8) 0.0230(8) 0.0019(6) -0.0003(6) -0.0021(6) C7 0.0283(9) 0.0156(8) 0.0258(9) -0.0033(6) 0.0028(7) 0.0006(6) C8 0.0305(9) 0.0174(8) 0.0255(9) -0.0010(6) 0.0005(7) -0.0003(7) C9 0.0436(11) 0.0249(9) 0.0445(11) -0.0038(8) -0.0069(9) -0.0114(8) C10 0.0588(14) 0.0390(12) 0.0524(13) -0.0007(10) -0.0145(11) -0.0088(10) C11 0.0472(11) 0.0151(8) 0.0390(11) -0.0016(7) -0.0006(8) -0.0024(8) C12 0.0849(17) 0.0303(11) 0.0425(13) -0.0003(9) 0.0126(12) 0.0086(11) C13 0.0267(9) 0.0170(8) 0.0275(9) 0.0027(6) 0.0024(7) -0.0059(7) C14 0.0311(9) 0.0283(9) 0.0368(10) -0.0052(8) 0.0007(8) -0.0002(8) C15 0.0455(11) 0.0359(10) 0.0344(10) -0.0088(8) -0.0009(9) -0.0086(9) C16 0.0364(11) 0.0364(11) 0.0410(11) 0.0042(9) -0.0103(9) -0.0138(9) C17 0.0264(10) 0.0352(11) 0.0576(13) 0.0034(9) -0.0043(9) -0.0020(8) C18 0.0288(9) 0.0261(9) 0.0412(11) -0.0030(8) 0.0034(8) -0.0030(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 S1 C13 1.7774(17) . ? S1 C5 1.8210(15) . ? F1 C3 1.3583(18) . ? F2 C3 1.3512(18) . ? O7 C4 1.4336(18) . ? O7 C1 1.4370(18) . ? O1 C7 1.3461(19) . ? O1 C6 1.4540(18) . ? O2 C7 1.1984(19) . ? O3 C8 1.384(2) . ? O3 C2 1.4053(18) . ? O4 C8 1.212(2) . ? N1 C8 1.337(2) . ? N1 C11 1.473(2) . ? N1 C9 1.473(2) . ? C1 C2 1.532(2) . ? C1 C6 1.550(2) . ? C2 C7 1.521(2) . ? C2 C3 1.559(2) . ? C3 C4 1.534(2) . ? C4 C5 1.536(2) . ? C5 C6 1.538(2) . ? C9 C10 1.504(3) . ? C11 C12 1.505(3) . ? C13 C14 1.390(2) . ? C13 C18 1.391(2) . ? C14 C15 1.387(2) . ? C15 C16 1.372(3) . ? C16 C17 1.382(3) . ? C17 C18 1.382(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 C13 S1 C5 98.97(7) . . ? C4 O7 C1 97.53(11) . . ? C7 O1 C6 110.16(12) . . ? C8 O3 C2 113.55(12) . . ? C8 N1 C11 117.81(15) . . ? C8 N1 C9 122.50(15) . . ? C11 N1 C9 119.69(14) . . ? O7 C1 C2 105.34(12) . . ? O7 C1 C6 105.33(12) . . ? C2 C1 C6 98.19(12) . . ? O3 C2 C7 112.60(13) . . ? O3 C2 C1 118.98(13) . . ? C7 C2 C1 104.48(12) . . ? O3 C2 C3 110.41(12) . . ? C7 C2 C3 110.31(12) . . ? C1 C2 C3 99.11(12) . . ? F2 C3 F1 106.72(12) . . ? F2 C3 C4 110.08(13) . . ? F1 C3 C4 113.20(13) . . ? F2 C3 C2 111.00(12) . . ? F1 C3 C2 112.81(13) . . ? C4 C3 C2 103.09(12) . . ? O7 C4 C3 99.90(12) . . ? O7 C4 C5 102.51(12) . . ? C3 C4 C5 110.36(13) . . ? C4 C5 C6 100.77(12) . . ? C4 C5 S1 107.51(11) . . ? C6 C5 S1 111.85(10) . . ? O1 C6 C5 111.83(12) . . ? O1 C6 C1 106.63(12) . . ? C5 C6 C1 101.70(12) . . ? O2 C7 O1 123.70(15) . . ? O2 C7 C2 127.91(15) . . ? O1 C7 C2 108.37(13) . . ? O4 C8 N1 127.40(16) . . ? O4 C8 O3 121.81(14) . . ? N1 C8 O3 110.78(14) . . ? N1 C9 C10 113.40(17) . . ? N1 C11 C12 113.92(15) . . ? C14 C13 C18 119.34(16) . . ? C14 C13 S1 119.64(13) . . ? C18 C13 S1 121.01(13) . . ? C15 C14 C13 119.94(17) . . ? C16 C15 C14 120.23(18) . . ? C15 C16 C17 120.34(18) . . ? C16 C17 C18 119.93(18) . . ? C17 C18 C13 120.21(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.524 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.055 #===END data_10b _database_code_depnum_ccdc_archive 'CCDC 272667' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 F2 O6 S' _chemical_formula_weight 386.36 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9999(5) _cell_length_b 8.3226(4) _cell_length_c 19.8738(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.6090(10) _cell_angle_gamma 90.00 _cell_volume 1648.65(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7626 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.53 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; absorption correction based on 9817 reflections (SADABS); Rint 0.026 and 0.019 before and after correction respectively. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11548 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2900 _reflns_number_gt 2664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^+0.5992P] 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 2900 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.75893(4) 0.94441(5) 0.03106(2) 0.02760(13) Uani 1 1 d . . . F1 F 1.15505(9) 0.70660(11) 0.06543(4) 0.0291(2) Uani 1 1 d . . . F2 F 1.22555(9) 0.86913(11) 0.14599(5) 0.0312(2) Uani 1 1 d . . . O1 O 0.94200(10) 0.89791(12) 0.17059(5) 0.0212(2) Uani 1 1 d . . . O2 O 1.14147(11) 0.78074(13) 0.28047(5) 0.0269(3) Uani 1 1 d . . . O3 O 1.26231(10) 0.58070(12) 0.23989(5) 0.0225(2) Uani 1 1 d . . . O4 O 1.07269(9) 0.50209(12) 0.15091(5) 0.0205(2) Uani 1 1 d . . . O5 O 0.99060(10) 0.30276(12) 0.08778(5) 0.0244(2) Uani 1 1 d . . . O6 O 0.86439(10) 0.51803(12) 0.09136(5) 0.0237(2) Uani 1 1 d . . . C1 C 0.92303(14) 0.72747(17) 0.17914(7) 0.0194(3) Uani 1 1 d . . . C2 C 1.06683(14) 0.66430(17) 0.17353(7) 0.0186(3) Uani 1 1 d . . . C3 C 1.11639(14) 0.78543(18) 0.12014(7) 0.0223(3) Uani 1 1 d . . . C4 C 0.99637(14) 0.89601(18) 0.10569(7) 0.0221(3) Uani 1 1 d . . . H4 H 1.0192 1.0045 0.0883 0.027 Uiso 1 1 calc R . . C5 C 0.89033(14) 0.80492(17) 0.06085(7) 0.0219(3) Uani 1 1 d . . . H5 H 0.9307 0.7507 0.0224 0.026 Uiso 1 1 calc R . . C6 C 0.84413(14) 0.68163(17) 0.11204(7) 0.0205(3) Uani 1 1 d . . . H6 H 0.7463 0.6982 0.1169 0.025 Uiso 1 1 calc R . . C7 C 0.85392(15) 0.68613(18) 0.24122(7) 0.0232(3) Uani 1 1 d . . . H7A H 0.9075 0.7256 0.2813 0.035 Uiso 1 1 calc R . . H7B H 0.8441 0.5693 0.2443 0.035 Uiso 1 1 calc R . . H7C H 0.7651 0.7365 0.2386 0.035 Uiso 1 1 calc R . . C8 C 1.15876(14) 0.68049(17) 0.23876(7) 0.0199(3) Uani 1 1 d . . . C9 C 1.35924(15) 0.6032(2) 0.29833(8) 0.0287(4) Uani 1 1 d . . . H9A H 1.3172 0.5767 0.3404 0.034 Uiso 1 1 calc R . . H9B H 1.3892 0.7166 0.3010 0.034 Uiso 1 1 calc R . . C10 C 1.47647(18) 0.4953(3) 0.29064(10) 0.0460(5) Uani 1 1 d . . . H10A H 1.4468 0.3830 0.2905 0.069 Uiso 1 1 calc R . . H10B H 1.5442 0.5126 0.3284 0.069 Uiso 1 1 calc R . . H10C H 1.5153 0.5194 0.2480 0.069 Uiso 1 1 calc R . . C11 C 0.97571(14) 0.43551(17) 0.10856(7) 0.0194(3) Uani 1 1 d . . . C12 C 0.64656(15) 0.80805(18) -0.01341(7) 0.0245(3) Uani 1 1 d . . . C13 C 0.68599(16) 0.7246(2) -0.06891(8) 0.0300(4) Uani 1 1 d . . . H13 H 0.7740 0.7382 -0.0828 0.036 Uiso 1 1 calc R . . C14 C 0.59705(17) 0.6217(2) -0.10401(8) 0.0337(4) Uani 1 1 d . . . H14 H 0.6250 0.5616 -0.1410 0.040 Uiso 1 1 calc R . . C15 C 0.46749(17) 0.6061(2) -0.08536(9) 0.0316(4) Uani 1 1 d . . . H15 H 0.4061 0.5370 -0.1102 0.038 Uiso 1 1 calc R . . C16 C 0.42718(16) 0.6903(2) -0.03088(9) 0.0317(4) Uani 1 1 d . . . H16 H 0.3378 0.6801 -0.0185 0.038 Uiso 1 1 calc R . . C17 C 0.51680(16) 0.78975(19) 0.00582(8) 0.0289(4) Uani 1 1 d . . . H17 H 0.4896 0.8455 0.0441 0.035 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 0.0316(2) 0.0222(2) 0.0276(2) 0.00170(15) -0.00603(16) 0.00599(16) F1 0.0295(5) 0.0370(5) 0.0217(5) 0.0023(4) 0.0081(4) 0.0051(4) F2 0.0239(5) 0.0336(5) 0.0352(5) 0.0074(4) -0.0034(4) -0.0109(4) O1 0.0262(5) 0.0154(5) 0.0219(5) 0.0003(4) 0.0024(4) -0.0005(4) O2 0.0310(6) 0.0259(6) 0.0234(6) -0.0062(5) -0.0010(4) 0.0025(5) O3 0.0201(5) 0.0253(6) 0.0214(5) -0.0021(4) -0.0033(4) 0.0017(4) O4 0.0205(5) 0.0182(5) 0.0224(5) -0.0040(4) -0.0011(4) 0.0013(4) O5 0.0284(6) 0.0200(6) 0.0246(6) -0.0048(4) 0.0014(4) -0.0003(4) O6 0.0247(5) 0.0178(5) 0.0274(6) -0.0028(4) -0.0062(4) 0.0003(4) C1 0.0214(7) 0.0145(7) 0.0221(7) -0.0003(6) 0.0011(6) 0.0006(6) C2 0.0209(7) 0.0156(7) 0.0191(7) -0.0012(6) 0.0011(6) -0.0001(6) C3 0.0218(7) 0.0248(8) 0.0206(7) -0.0006(6) 0.0021(6) -0.0039(6) C4 0.0256(8) 0.0206(7) 0.0202(7) 0.0033(6) 0.0017(6) -0.0018(6) C5 0.0232(7) 0.0205(7) 0.0217(7) 0.0014(6) -0.0003(6) 0.0027(6) C6 0.0202(7) 0.0170(7) 0.0238(7) -0.0004(6) -0.0004(6) 0.0011(6) C7 0.0235(7) 0.0220(8) 0.0247(8) 0.0007(6) 0.0054(6) 0.0004(6) C8 0.0206(7) 0.0188(7) 0.0202(7) 0.0012(6) 0.0018(6) -0.0021(6) C9 0.0253(8) 0.0362(9) 0.0230(8) -0.0019(7) -0.0070(6) -0.0011(7) C10 0.0308(9) 0.0521(12) 0.0517(12) -0.0092(10) -0.0168(8) 0.0086(9) C11 0.0219(7) 0.0197(8) 0.0168(7) 0.0003(6) 0.0021(6) -0.0018(6) C12 0.0256(8) 0.0239(8) 0.0232(8) 0.0058(6) -0.0033(6) 0.0053(6) C13 0.0226(8) 0.0402(10) 0.0269(8) 0.0002(7) 0.0012(6) 0.0033(7) C14 0.0329(9) 0.0404(10) 0.0272(8) -0.0041(7) -0.0014(7) 0.0048(8) C15 0.0291(8) 0.0307(9) 0.0337(9) 0.0049(7) -0.0058(7) -0.0013(7) C16 0.0246(8) 0.0324(9) 0.0382(9) 0.0110(7) 0.0039(7) 0.0030(7) C17 0.0312(9) 0.0293(9) 0.0269(8) 0.0048(7) 0.0060(7) 0.0095(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 S1 C12 1.7810(16) . ? S1 C5 1.8166(15) . ? F1 C3 1.3527(17) . ? F2 C3 1.3604(17) . ? O1 C4 1.4394(17) . ? O1 C1 1.4430(17) . ? O2 C8 1.1984(18) . ? O3 C8 1.3262(18) . ? O3 C9 1.4637(17) . ? O4 C11 1.3508(17) . ? O4 C2 1.4256(17) . ? O5 C11 1.1929(17) . ? O6 C11 1.3291(17) . ? O6 C6 1.4412(17) . ? C1 C7 1.502(2) . ? C1 C6 1.542(2) . ? C1 C2 1.5435(19) . ? C2 C8 1.534(2) . ? C2 C3 1.5725(19) . ? C3 C4 1.521(2) . ? C4 C5 1.530(2) . ? C5 C6 1.542(2) . ? C9 C10 1.495(2) . ? C12 C13 1.387(2) . ? C12 C17 1.390(2) . ? C13 C14 1.383(2) . ? C14 C15 1.382(2) . ? C15 C16 1.377(2) . ? C16 C17 1.384(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 C12 S1 C5 99.53(7) . . ? C4 O1 C1 99.06(10) . . ? C8 O3 C9 113.55(11) . . ? C11 O4 C2 122.64(11) . . ? C11 O6 C6 123.29(11) . . ? O1 C1 C7 113.31(12) . . ? O1 C1 C6 101.79(11) . . ? C7 C1 C6 114.62(12) . . ? O1 C1 C2 101.20(11) . . ? C7 C1 C2 118.31(12) . . ? C6 C1 C2 105.55(11) . . ? O4 C2 C8 108.23(11) . . ? O4 C2 C1 114.05(11) . . ? C8 C2 C1 114.06(12) . . ? O4 C2 C3 111.78(11) . . ? C8 C2 C3 108.30(11) . . ? C1 C2 C3 100.16(11) . . ? F1 C3 F2 106.23(11) . . ? F1 C3 C4 114.44(12) . . ? F2 C3 C4 111.01(12) . . ? F1 C3 C2 110.94(12) . . ? F2 C3 C2 111.11(11) . . ? C4 C3 C2 103.21(11) . . ? O1 C4 C3 100.75(11) . . ? O1 C4 C5 103.50(11) . . ? C3 C4 C5 108.03(12) . . ? C4 C5 C6 100.13(11) . . ? C4 C5 S1 108.81(10) . . ? C6 C5 S1 113.15(10) . . ? O6 C6 C5 112.60(12) . . ? O6 C6 C1 113.98(11) . . ? C5 C6 C1 104.26(11) . . ? O2 C8 O3 125.46(13) . . ? O2 C8 C2 122.40(13) . . ? O3 C8 C2 111.93(12) . . ? O3 C9 C10 108.47(13) . . ? O5 C11 O6 120.98(13) . . ? O5 C11 O4 119.49(13) . . ? O6 C11 O4 119.52(12) . . ? C13 C12 C17 119.67(15) . . ? C13 C12 S1 120.35(12) . . ? C17 C12 S1 119.93(12) . . ? C14 C13 C12 119.93(15) . . ? C15 C14 C13 120.12(16) . . ? C16 C15 C14 120.20(16) . . ? C15 C16 C17 120.05(15) . . ? C16 C17 C12 119.99(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.296 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.047 #===END data_11b _database_code_depnum_ccdc_archive 'CCDC 272668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 F2 N O6 S' _chemical_formula_weight 459.50 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' N N 0.0061 0.0033 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.806(2) _cell_length_b 22.250(6) _cell_length_c 11.795(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.871(4) _cell_angle_gamma 90.00 _cell_volume 2283.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5585 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 20.74 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16416 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4020 _reflns_number_gt 3394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.4490P] 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 4020 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 S1 S 0.29684(7) 0.62420(2) -0.02181(4) 0.04892(18) Uani 1 1 d . . . F1 F 0.48736(13) 0.54217(5) 0.31190(9) 0.0438(3) Uani 1 1 d . . . F2 F 0.27589(14) 0.54789(5) 0.38310(9) 0.0488(3) Uani 1 1 d . . . N1 N 0.79618(17) 0.68601(7) 0.46646(14) 0.0402(4) Uani 1 1 d . . . O1 O 0.19596(13) 0.64708(5) 0.23861(11) 0.0351(3) Uani 1 1 d . . . O2 O 0.24392(14) 0.66547(7) 0.51309(11) 0.0447(4) Uani 1 1 d . . . O3 O 0.46019(15) 0.61266(6) 0.56700(11) 0.0402(3) Uani 1 1 d . . . O4 O 0.57684(12) 0.64333(5) 0.38849(10) 0.0293(3) Uani 1 1 d . . . O5 O 0.56955(14) 0.72834(6) 0.49266(11) 0.0384(3) Uani 1 1 d . . . O6 O 0.56054(14) 0.70508(6) 0.19063(11) 0.0404(3) Uani 1 1 d . . . H6 H 0.5760 0.7269 0.1354 0.061 Uiso 1 1 calc R . . C1 C 0.32904(19) 0.68363(8) 0.28109(15) 0.0310(4) Uani 1 1 d . . . C2 C 0.41412(19) 0.64088(8) 0.37536(15) 0.0292(4) Uani 1 1 d . . . C3 C 0.3670(2) 0.57859(8) 0.31936(15) 0.0331(4) Uani 1 1 d . . . C4 C 0.2751(2) 0.59538(8) 0.20534(15) 0.0319(4) Uani 1 1 d . . . H4 H 0.2054 0.5628 0.1698 0.038 Uiso 1 1 calc R . . C5 C 0.3835(2) 0.61986(8) 0.12672(15) 0.0324(4) Uani 1 1 d . . . H5 H 0.4824 0.5970 0.1361 0.039 Uiso 1 1 calc R . . C6 C 0.4079(2) 0.68506(8) 0.17270(15) 0.0329(4) Uani 1 1 d . . . H6A H 0.3473 0.7126 0.1158 0.039 Uiso 1 1 calc R . . C7 C 0.2807(2) 0.74503(8) 0.31477(18) 0.0414(5) Uani 1 1 d . . . H7A H 0.2113 0.7629 0.2507 0.062 Uiso 1 1 calc R . . H7B H 0.3718 0.7706 0.3339 0.062 Uiso 1 1 calc R . . H7C H 0.2277 0.7417 0.3817 0.062 Uiso 1 1 calc R . . C8 C 0.3606(2) 0.64301(8) 0.49320(16) 0.0333(4) Uani 1 1 d . . . C9 C 0.4332(3) 0.60910(11) 0.68506(17) 0.0542(6) Uani 1 1 d . . . H9A H 0.3862 0.5699 0.6992 0.065 Uiso 1 1 calc R . . H9B H 0.3625 0.6415 0.7011 0.065 Uiso 1 1 calc R . . C10 C 0.5807(4) 0.61554(16) 0.7587(2) 0.0885(10) Uani 1 1 d . . . H10A H 0.6528 0.5856 0.7372 0.133 Uiso 1 1 calc R . . H10B H 0.5673 0.6094 0.8389 0.133 Uiso 1 1 calc R . . H10C H 0.6214 0.6560 0.7497 0.133 Uiso 1 1 calc R . . C11 C 0.6443(2) 0.68960(8) 0.45287(15) 0.0321(4) Uani 1 1 d . . . C12 C 0.8775(2) 0.63659(10) 0.41952(19) 0.0466(5) Uani 1 1 d . . . H12A H 0.9758 0.6518 0.3997 0.056 Uiso 1 1 calc R . . H12B H 0.8146 0.6218 0.3481 0.056 Uiso 1 1 calc R . . C13 C 0.9097(3) 0.58557(12) 0.5026(3) 0.0756(8) Uani 1 1 d . . . H13A H 0.9717 0.6001 0.5735 0.113 Uiso 1 1 calc R . . H13B H 0.9659 0.5540 0.4688 0.113 Uiso 1 1 calc R . . H13C H 0.8124 0.5693 0.5200 0.113 Uiso 1 1 calc R . . C14 C 0.8868(2) 0.73245(11) 0.5337(2) 0.0625(7) Uani 1 1 d . . . H14A H 0.8355 0.7437 0.5997 0.075 Uiso 1 1 calc R . . H14B H 0.9894 0.7160 0.5645 0.075 Uiso 1 1 calc R . . C15 C 0.9058(3) 0.78602(13) 0.4659(3) 0.0970(11) Uani 1 1 d . . . H15A H 0.9517 0.7748 0.3983 0.145 Uiso 1 1 calc R . . H15B H 0.9732 0.8147 0.5126 0.145 Uiso 1 1 calc R . . H15C H 0.8053 0.8046 0.4412 0.145 Uiso 1 1 calc R . . C16 C 0.2385(2) 0.55060(9) -0.06201(16) 0.0379(5) Uani 1 1 d . . . C17 C 0.2963(2) 0.49881(9) -0.00679(17) 0.0413(5) Uani 1 1 d . . . H17 H 0.3733 0.5012 0.0590 0.050 Uiso 1 1 calc R . . C18 C 0.2416(2) 0.44351(10) -0.04767(18) 0.0473(5) Uani 1 1 d . . . H18 H 0.2805 0.4080 -0.0089 0.057 Uiso 1 1 calc R . . C19 C 0.1322(3) 0.43909(11) -0.14336(18) 0.0541(6) Uani 1 1 d . . . H19 H 0.0947 0.4009 -0.1706 0.065 Uiso 1 1 calc R . . C20 C 0.0775(3) 0.49051(12) -0.19936(19) 0.0596(7) Uani 1 1 d . . . H20 H 0.0035 0.4877 -0.2669 0.072 Uiso 1 1 calc R . . C21 C 0.1282(2) 0.54589(11) -0.15905(17) 0.0503(6) Uani 1 1 d . . . H21 H 0.0876 0.5812 -0.1978 0.060 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 0.0717(4) 0.0409(3) 0.0304(3) 0.0039(2) -0.0042(3) -0.0085(3) F1 0.0535(7) 0.0320(6) 0.0420(6) -0.0037(5) -0.0053(5) 0.0090(5) F2 0.0656(8) 0.0446(7) 0.0364(6) 0.0027(5) 0.0082(6) -0.0242(6) N1 0.0249(8) 0.0485(10) 0.0463(10) -0.0173(8) 0.0030(7) -0.0008(7) O1 0.0262(6) 0.0371(7) 0.0408(7) -0.0034(6) 0.0009(5) -0.0031(5) O2 0.0306(7) 0.0604(9) 0.0454(8) -0.0021(7) 0.0128(6) 0.0004(7) O3 0.0459(8) 0.0465(8) 0.0289(7) 0.0018(6) 0.0086(6) 0.0065(6) O4 0.0238(6) 0.0334(7) 0.0303(7) -0.0056(5) 0.0031(5) -0.0001(5) O5 0.0285(7) 0.0426(8) 0.0441(8) -0.0157(6) 0.0060(6) 0.0015(6) O6 0.0378(7) 0.0465(8) 0.0363(7) 0.0063(6) 0.0035(6) -0.0143(6) C1 0.0245(9) 0.0309(9) 0.0359(10) -0.0018(8) -0.0009(7) -0.0029(7) C2 0.0246(9) 0.0312(9) 0.0313(9) -0.0016(7) 0.0033(7) -0.0019(7) C3 0.0369(10) 0.0292(9) 0.0332(10) 0.0014(8) 0.0054(8) -0.0035(8) C4 0.0315(9) 0.0298(9) 0.0330(10) -0.0032(8) 0.0003(8) -0.0044(8) C5 0.0348(10) 0.0322(10) 0.0286(9) 0.0014(7) 0.0003(8) -0.0020(8) C6 0.0320(10) 0.0321(10) 0.0325(10) 0.0032(8) -0.0016(8) -0.0042(8) C7 0.0407(11) 0.0331(10) 0.0490(12) -0.0015(9) 0.0027(9) 0.0043(8) C8 0.0290(10) 0.0346(10) 0.0360(10) -0.0039(8) 0.0044(8) -0.0052(8) C9 0.0770(16) 0.0559(14) 0.0337(11) 0.0075(10) 0.0209(11) 0.0148(12) C10 0.098(2) 0.132(3) 0.0311(13) 0.0035(15) -0.0027(14) 0.008(2) C11 0.0281(9) 0.0380(10) 0.0296(9) -0.0053(8) 0.0027(8) -0.0007(8) C12 0.0281(10) 0.0575(13) 0.0547(13) -0.0176(11) 0.0079(9) 0.0046(9) C13 0.0676(17) 0.0573(16) 0.104(2) 0.0024(15) 0.0183(16) 0.0160(13) C14 0.0285(11) 0.0687(16) 0.0882(18) -0.0372(14) 0.0020(11) -0.0034(11) C15 0.0612(18) 0.0672(19) 0.160(3) -0.030(2) 0.0101(19) -0.0138(15) C16 0.0381(11) 0.0477(12) 0.0284(10) -0.0006(8) 0.0068(8) -0.0090(9) C17 0.0400(11) 0.0467(12) 0.0355(11) -0.0057(9) 0.0007(9) -0.0033(9) C18 0.0508(13) 0.0457(12) 0.0455(12) -0.0083(10) 0.0078(10) -0.0068(10) C19 0.0616(14) 0.0623(15) 0.0395(12) -0.0135(11) 0.0109(11) -0.0270(12) C20 0.0577(14) 0.0849(18) 0.0330(12) -0.0018(12) -0.0033(10) -0.0339(13) C21 0.0492(13) 0.0641(14) 0.0343(11) 0.0087(10) -0.0034(9) -0.0155(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C16 1.759(2) . ? S1 C5 1.8023(18) . ? F1 C3 1.348(2) . ? F2 C3 1.364(2) . ? N1 C11 1.325(2) . ? N1 C14 1.463(3) . ? N1 C12 1.466(2) . ? O1 C4 1.431(2) . ? O1 C1 1.451(2) . ? O2 C8 1.198(2) . ? O3 C8 1.322(2) . ? O3 C9 1.450(2) . ? O4 C11 1.360(2) . ? O4 C2 1.418(2) . ? O5 C11 1.222(2) . ? O6 C6 1.401(2) . ? C1 C7 1.502(3) . ? C1 C6 1.546(3) . ? C1 C2 1.564(2) . ? C2 C8 1.535(3) . ? C2 C3 1.563(2) . ? C3 C4 1.506(2) . ? C4 C5 1.530(3) . ? C5 C6 1.552(2) . ? C9 C10 1.454(3) . ? C12 C13 1.498(3) . ? C14 C15 1.460(4) . ? C16 C17 1.382(3) . ? C16 C21 1.386(3) . ? C17 C18 1.381(3) . ? C18 C19 1.370(3) . ? C19 C20 1.371(3) . ? C20 C21 1.371(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 C16 S1 C5 105.92(9) . . ? C11 N1 C14 118.65(16) . . ? C11 N1 C12 122.83(16) . . ? C14 N1 C12 118.50(16) . . ? C4 O1 C1 98.27(12) . . ? C8 O3 C9 118.04(15) . . ? C11 O4 C2 115.91(13) . . ? O1 C1 C7 110.77(14) . . ? O1 C1 C6 99.66(13) . . ? C7 C1 C6 112.41(15) . . ? O1 C1 C2 100.23(13) . . ? C7 C1 C2 119.29(15) . . ? C6 C1 C2 111.93(14) . . ? O4 C2 C8 110.22(14) . . ? O4 C2 C3 106.14(13) . . ? C8 C2 C3 108.14(14) . . ? O4 C2 C1 114.80(14) . . ? C8 C2 C1 116.40(14) . . ? C3 C2 C1 99.90(13) . . ? F1 C3 F2 105.67(14) . . ? F1 C3 C4 114.24(15) . . ? F2 C3 C4 109.61(14) . . ? F1 C3 C2 113.60(14) . . ? F2 C3 C2 110.57(14) . . ? C4 C3 C2 103.21(14) . . ? O1 C4 C3 99.90(14) . . ? O1 C4 C5 104.82(14) . . ? C3 C4 C5 109.27(14) . . ? C4 C5 C6 100.76(14) . . ? C4 C5 S1 113.46(12) . . ? C6 C5 S1 107.74(12) . . ? O6 C6 C1 115.12(14) . . ? O6 C6 C5 115.33(15) . . ? C1 C6 C5 102.35(14) . . ? O2 C8 O3 125.88(17) . . ? O2 C8 C2 125.60(17) . . ? O3 C8 C2 108.39(15) . . ? O3 C9 C10 107.7(2) . . ? O5 C11 N1 126.15(17) . . ? O5 C11 O4 122.26(15) . . ? N1 C11 O4 111.58(15) . . ? N1 C12 C13 112.04(19) . . ? C15 C14 N1 112.2(2) . . ? C17 C16 C21 119.11(19) . . ? C17 C16 S1 125.33(15) . . ? C21 C16 S1 115.54(16) . . ? C18 C17 C16 119.70(19) . . ? C19 C18 C17 121.0(2) . . ? C18 C19 C20 119.2(2) . . ? C21 C20 C19 120.8(2) . . ? C20 C21 C16 120.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.540 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.041 #===END data_27 _database_code_depnum_ccdc_archive 'CCDC 272669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 F2 O5 S' _chemical_formula_weight 386.40 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.875(3) _cell_length_b 6.5609(12) _cell_length_c 15.029(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.158(3) _cell_angle_gamma 90.00 _cell_volume 1759.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2065 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 24.54 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.231 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12099 _diffrn_reflns_av_R_equivalents 0.0728 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3096 _reflns_number_gt 2149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.3417P] 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 3096 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.17893(6) 0.63664(14) 0.46781(6) 0.0348(3) Uani 1 1 d . . . F1 F 0.36018(16) 0.1113(4) 0.36103(15) 0.0765(9) Uani 1 1 d . . . F2 F 0.39660(14) 0.4206(5) 0.38312(16) 0.0814(10) Uani 1 1 d . . . O1 O 0.21602(14) 0.2790(3) 0.32305(15) 0.0333(6) Uani 1 1 d . . . O2 O 0.36387(15) 0.5145(5) 0.21746(17) 0.0503(8) Uani 1 1 d . . . O3 O 0.35193(15) 0.2843(4) 0.10780(16) 0.0470(7) Uani 1 1 d . . . O4 O 0.19935(15) 0.5473(4) 0.55239(15) 0.0417(7) Uani 1 1 d . . . O5 O 0.16854(16) 0.8516(4) 0.46297(16) 0.0453(7) Uani 1 1 d . . . C1 C 0.2382(2) 0.4158(5) 0.2542(2) 0.0284(8) Uani 1 1 d . . . C1' C 0.1880(2) 0.3909(5) 0.1726(2) 0.0361(9) Uani 1 1 d . . . H1'1 H 0.1884 0.2481 0.1535 0.054 Uiso 1 1 calc R . . H1'2 H 0.2058 0.4775 0.1250 0.054 Uiso 1 1 calc R . . H1'3 H 0.1369 0.4307 0.1855 0.054 Uiso 1 1 calc R . . C2 C 0.3209(2) 0.3552(6) 0.2495(2) 0.0372(9) Uani 1 1 d . . . C3 C 0.3396(2) 0.3099(7) 0.3485(3) 0.0471(11) Uani 1 1 d . . . C4 C 0.2673(2) 0.3460(6) 0.3921(2) 0.0394(10) Uani 1 1 d . . . H4 H 0.2631 0.2724 0.4499 0.047 Uiso 1 1 calc R . . C5 C 0.2518(2) 0.5734(5) 0.3969(2) 0.0342(9) Uani 1 1 d . . . H5 H 0.2988 0.6463 0.4175 0.041 Uiso 1 1 calc R . . C6 C 0.2340(2) 0.6195(5) 0.3002(2) 0.0311(9) Uani 1 1 d . . . C6' C 0.2171(2) 0.7938(6) 0.2639(3) 0.0466(11) Uani 1 1 d . . . H6'1 H 0.2149 0.9125 0.2999 0.056 Uiso 1 1 calc R . . H6'2 H 0.2070 0.8029 0.2013 0.056 Uiso 1 1 calc R . . C7 C 0.3356(2) 0.1803(6) 0.1863(2) 0.0435(10) Uani 1 1 d . . . H7A H 0.3785 0.0961 0.2088 0.052 Uiso 1 1 calc R . . H7B H 0.2908 0.0924 0.1767 0.052 Uiso 1 1 calc R . . C8 C 0.3941(2) 0.4555(7) 0.1343(3) 0.0517(12) Uani 1 1 d . . . C9 C 0.4758(3) 0.4059(10) 0.1495(4) 0.089(2) Uani 1 1 d . . . H9A H 0.4824 0.3062 0.1978 0.134 Uiso 1 1 calc R . . H9B H 0.5036 0.5304 0.1657 0.134 Uiso 1 1 calc R . . H9C H 0.4947 0.3488 0.0948 0.134 Uiso 1 1 calc R . . C10 C 0.3783(3) 0.6233(8) 0.0687(3) 0.0753(16) Uani 1 1 d . . . H10A H 0.3938 0.5808 0.0099 0.113 Uiso 1 1 calc R . . H10B H 0.4064 0.7455 0.0879 0.113 Uiso 1 1 calc R . . H10C H 0.3246 0.6537 0.0652 0.113 Uiso 1 1 calc R . . C11 C 0.0981(2) 0.5175(5) 0.4238(2) 0.0335(9) Uani 1 1 d . . . C12 C 0.0825(2) 0.3216(6) 0.4485(2) 0.0421(10) Uani 1 1 d . . . H12 H 0.1155 0.2507 0.4894 0.050 Uiso 1 1 calc R . . C13 C 0.0189(3) 0.2298(7) 0.4136(3) 0.0512(12) Uani 1 1 d . . . H13 H 0.0077 0.0937 0.4298 0.061 Uiso 1 1 calc R . . C14 C -0.0285(3) 0.3333(7) 0.3554(3) 0.0548(12) Uani 1 1 d . . . H14 H -0.0727 0.2683 0.3315 0.066 Uiso 1 1 calc R . . C15 C -0.0134(2) 0.5287(8) 0.3312(3) 0.0520(12) Uani 1 1 d . . . H15 H -0.0471 0.5994 0.2911 0.062 Uiso 1 1 calc R . . C16 C 0.0504(2) 0.6231(6) 0.3649(2) 0.0417(10) Uani 1 1 d . . . H16 H 0.0616 0.7587 0.3479 0.050 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 0.0542(6) 0.0314(5) 0.0190(5) -0.0025(4) 0.0033(4) 0.0043(5) F1 0.088(2) 0.102(2) 0.0392(15) 0.0111(14) 0.0112(14) 0.0632(18) F2 0.0442(16) 0.161(3) 0.0374(15) -0.0201(17) -0.0072(12) -0.0028(17) O1 0.0488(16) 0.0259(13) 0.0259(13) 0.0034(10) 0.0089(12) 0.0030(11) O2 0.0475(18) 0.076(2) 0.0290(15) -0.0145(14) 0.0156(13) -0.0239(15) O3 0.0509(18) 0.0622(19) 0.0286(15) -0.0093(13) 0.0101(13) -0.0039(15) O4 0.0615(18) 0.0483(17) 0.0152(12) 0.0004(11) 0.0011(12) 0.0085(14) O5 0.075(2) 0.0272(14) 0.0333(15) -0.0041(12) 0.0020(14) 0.0064(14) C1 0.041(2) 0.0243(19) 0.0204(17) 0.0030(14) 0.0052(15) -0.0052(15) C1' 0.045(2) 0.036(2) 0.0265(19) -0.0058(16) 0.0006(17) -0.0017(18) C2 0.037(2) 0.048(2) 0.027(2) -0.0025(18) 0.0064(17) -0.0064(19) C3 0.045(3) 0.065(3) 0.032(2) -0.003(2) -0.001(2) 0.011(2) C4 0.048(2) 0.050(2) 0.0209(19) 0.0059(17) 0.0038(17) 0.014(2) C5 0.040(2) 0.037(2) 0.0250(19) -0.0021(16) 0.0005(17) -0.0064(17) C6 0.045(2) 0.026(2) 0.0227(18) -0.0014(15) 0.0049(16) -0.0085(16) C6' 0.082(3) 0.027(2) 0.032(2) -0.0015(17) 0.011(2) -0.004(2) C7 0.047(3) 0.055(3) 0.029(2) -0.0044(18) 0.0102(18) 0.006(2) C8 0.048(3) 0.072(3) 0.036(2) -0.007(2) 0.012(2) -0.019(2) C9 0.040(3) 0.153(6) 0.076(4) -0.027(4) 0.015(3) -0.019(3) C10 0.103(4) 0.076(4) 0.049(3) 0.000(3) 0.021(3) -0.033(3) C11 0.048(2) 0.033(2) 0.0203(18) -0.0053(15) 0.0108(17) 0.0049(18) C12 0.065(3) 0.037(2) 0.025(2) 0.0012(17) 0.0095(19) 0.002(2) C13 0.071(3) 0.047(3) 0.036(2) 0.001(2) 0.012(2) -0.015(2) C14 0.053(3) 0.070(3) 0.042(3) -0.012(2) 0.010(2) -0.010(2) C15 0.046(3) 0.074(3) 0.035(2) -0.006(2) 0.000(2) 0.010(2) C16 0.054(3) 0.041(2) 0.030(2) -0.0019(18) 0.0042(19) 0.010(2) _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 O5 1.424(2) . ? S1 O4 1.429(2) . ? S1 C11 1.741(4) . ? S1 C5 1.777(4) . ? F1 C3 1.364(5) . ? F2 C3 1.334(5) . ? O1 C4 1.416(4) . ? O1 C1 1.442(4) . ? O2 C2 1.398(4) . ? O2 C8 1.441(4) . ? O3 C8 1.399(5) . ? O3 C7 1.407(4) . ? C1 C1' 1.488(5) . ? C1 C6 1.508(5) . ? C1 C2 1.537(5) . ? C2 C7 1.522(5) . ? C2 C3 1.535(5) . ? C3 C4 1.501(5) . ? C4 C5 1.519(5) . ? C5 C6 1.501(5) . ? C6 C6' 1.295(5) . ? C8 C10 1.495(6) . ? C8 C9 1.501(6) . ? C11 C12 1.370(5) . ? C11 C16 1.382(5) . ? C12 C13 1.365(6) . ? C13 C14 1.365(6) . ? C14 C15 1.364(6) . ? C15 C16 1.369(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 S1 O4 118.55(15) . . ? O5 S1 C11 108.80(18) . . ? O4 S1 C11 108.65(17) . . ? O5 S1 C5 107.37(17) . . ? O4 S1 C5 106.15(16) . . ? C11 S1 C5 106.71(17) . . ? C4 O1 C1 98.1(3) . . ? C2 O2 C8 109.7(3) . . ? C8 O3 C7 106.5(3) . . ? O1 C1 C1' 110.3(3) . . ? O1 C1 C6 101.6(3) . . ? C1' C1 C6 115.6(3) . . ? O1 C1 C2 100.1(3) . . ? C1' C1 C2 118.1(3) . . ? C6 C1 C2 108.8(3) . . ? O2 C2 C7 103.4(3) . . ? O2 C2 C3 112.6(3) . . ? C7 C2 C3 115.0(3) . . ? O2 C2 C1 111.7(3) . . ? C7 C2 C1 115.0(3) . . ? C3 C2 C1 99.4(3) . . ? F2 C3 F1 105.8(3) . . ? F2 C3 C4 113.7(3) . . ? F1 C3 C4 108.8(4) . . ? F2 C3 C2 113.2(4) . . ? F1 C3 C2 111.2(3) . . ? C4 C3 C2 104.2(3) . . ? O1 C4 C3 99.7(3) . . ? O1 C4 C5 103.2(3) . . ? C3 C4 C5 109.8(3) . . ? C6 C5 C4 100.5(3) . . ? C6 C5 S1 114.2(3) . . ? C4 C5 S1 113.5(3) . . ? C6' C6 C5 128.1(3) . . ? C6' C6 C1 127.3(3) . . ? C5 C6 C1 104.6(3) . . ? O3 C7 C2 102.0(3) . . ? O3 C8 O2 104.0(3) . . ? O3 C8 C10 108.9(4) . . ? O2 C8 C10 108.0(4) . . ? O3 C8 C9 111.9(4) . . ? O2 C8 C9 109.5(4) . . ? C10 C8 C9 113.9(4) . . ? C12 C11 C16 121.0(4) . . ? C12 C11 S1 119.7(3) . . ? C16 C11 S1 119.3(3) . . ? C13 C12 C11 119.2(4) . . ? C12 C13 C14 120.1(4) . . ? C15 C14 C13 120.9(4) . . ? C14 C15 C16 120.0(4) . . ? C15 C16 C11 118.8(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.282 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.059 #===END data_46b _database_code_depnum_ccdc_archive 'CCDC 272670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 F2 O4' _chemical_formula_weight 340.36 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5327(18) _cell_length_b 11.552(2) _cell_length_c 16.158(3) _cell_angle_alpha 75.465(3) _cell_angle_beta 71.827(3) _cell_angle_gamma 68.790(3) _cell_volume 1720.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5631 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.106 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12601 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6014 _reflns_number_gt 5077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.0800P] 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 6014 _refine_ls_number_parameters 441 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 F1 F 0.83581(10) -0.06555(9) 0.37052(6) 0.0494(3) Uani 1 1 d . . . F2 F 1.01644(9) -0.14009(8) 0.26849(6) 0.0453(2) Uani 1 1 d . . . O1 O 0.62896(10) 0.13805(9) 0.16050(7) 0.0329(2) Uani 1 1 d . . . H1 H 0.5504 0.1926 0.1731 0.049 Uiso 1 1 calc R . . O2 O 0.89924(9) -0.02276(8) 0.13713(6) 0.0273(2) Uani 1 1 d . . . O3 O 0.83568(10) -0.20079(9) 0.18593(6) 0.0310(2) Uani 1 1 d . . . O4 O 0.69794(10) 0.33799(9) 0.19586(6) 0.0321(2) Uani 1 1 d . . . C1 C 0.70601(14) 0.12331(13) 0.22227(9) 0.0262(3) Uani 1 1 d . . . C1' C 0.60767(15) 0.14434(14) 0.31246(10) 0.0353(4) Uani 1 1 d . . . H1'1 H 0.5359 0.2265 0.3073 0.053 Uiso 1 1 calc R . . H1'2 H 0.6614 0.1418 0.3530 0.053 Uiso 1 1 calc R . . H1'3 H 0.5623 0.0782 0.3352 0.053 Uiso 1 1 calc R . . C2 C 0.80971(14) -0.01093(13) 0.22314(9) 0.0262(3) Uani 1 1 d . . . C3 C 0.90485(15) -0.03423(14) 0.28452(10) 0.0337(3) Uani 1 1 d . . . C4 C 0.95620(16) 0.07149(15) 0.27793(11) 0.0385(4) Uani 1 1 d . . . H4 H 1.0281 0.0586 0.3061 0.046 Uiso 1 1 calc R . . C5 C 0.90542(15) 0.18304(15) 0.23418(10) 0.0354(4) Uani 1 1 d . . . H5 H 0.9430 0.2475 0.2320 0.043 Uiso 1 1 calc R . . C6 C 0.79243(14) 0.21438(12) 0.18777(9) 0.0281(3) Uani 1 1 d . . . H6 H 0.8374 0.2101 0.1237 0.034 Uiso 1 1 calc R . . C7 C 0.74047(15) -0.11378(13) 0.24277(10) 0.0302(3) Uani 1 1 d . . . H7A H 0.7296 -0.1537 0.3054 0.036 Uiso 1 1 calc R . . H7B H 0.6471 -0.0795 0.2293 0.036 Uiso 1 1 calc R . . C8 C 0.89967(15) -0.13098(13) 0.10868(9) 0.0308(3) Uani 1 1 d . . . C9 C 1.04886(17) -0.20951(14) 0.07665(11) 0.0420(4) Uani 1 1 d . . . H9A H 1.0975 -0.2339 0.1240 0.063 Uiso 1 1 calc R . . H9B H 1.0967 -0.1607 0.0258 0.063 Uiso 1 1 calc R . . H9C H 1.0497 -0.2852 0.0592 0.063 Uiso 1 1 calc R . . C10 C 0.81585(18) -0.08856(15) 0.03984(10) 0.0415(4) Uani 1 1 d . . . H10A H 0.8086 -0.1622 0.0241 0.062 Uiso 1 1 calc R . . H10B H 0.8630 -0.0419 -0.0128 0.062 Uiso 1 1 calc R . . H10C H 0.7215 -0.0341 0.0635 0.062 Uiso 1 1 calc R . . C11 C 0.75119(16) 0.43447(14) 0.13871(10) 0.0354(4) Uani 1 1 d . . . H11A H 0.8046 0.4073 0.0809 0.043 Uiso 1 1 calc R . . H11B H 0.8155 0.4514 0.1643 0.043 Uiso 1 1 calc R . . C12 C 0.63176(15) 0.55100(13) 0.12672(9) 0.0294(3) Uani 1 1 d . . . C13 C 0.62815(17) 0.66390(14) 0.14295(10) 0.0371(4) Uani 1 1 d . . . H13 H 0.6998 0.6669 0.1656 0.045 Uiso 1 1 calc R . . C14 C 0.52195(19) 0.77226(15) 0.12668(12) 0.0465(4) Uani 1 1 d . . . H14 H 0.5208 0.8495 0.1380 0.056 Uiso 1 1 calc R . . C15 C 0.41798(19) 0.76909(16) 0.09423(12) 0.0514(5) Uani 1 1 d . . . H15 H 0.3449 0.8440 0.0826 0.062 Uiso 1 1 calc R . . C16 C 0.42004(18) 0.65646(17) 0.07852(12) 0.0497(4) Uani 1 1 d . . . H16 H 0.3480 0.6538 0.0561 0.060 Uiso 1 1 calc R . . C17 C 0.52537(16) 0.54831(15) 0.09505(11) 0.0390(4) Uani 1 1 d . . . H17 H 0.5253 0.4710 0.0847 0.047 Uiso 1 1 calc R . . F1A F 1.26059(9) 0.18051(8) 0.37951(6) 0.0434(2) Uani 1 1 d . . . F2A F 1.22194(10) 0.35037(9) 0.42849(6) 0.0492(3) Uani 1 1 d . . . O1A O 0.99948(10) 0.54421(9) 0.22391(6) 0.0329(2) Uani 1 1 d . . . H1A H 0.9440 0.6177 0.2252 0.049 Uiso 1 1 calc R . . O2A O 1.13235(9) 0.29007(9) 0.25267(6) 0.0267(2) Uani 1 1 d . . . O3A O 1.35107(10) 0.30716(9) 0.19292(7) 0.0341(3) Uani 1 1 d . . . O4A O 0.76607(10) 0.54494(9) 0.37522(7) 0.0347(3) Uani 1 1 d . . . C1A C 1.01155(15) 0.48560(13) 0.31082(9) 0.0275(3) Uani 1 1 d . . . C1" C 1.02002(17) 0.57775(14) 0.35979(10) 0.0365(4) Uani 1 1 d . . . H1"1 H 1.1057 0.6014 0.3307 0.055 Uiso 1 1 calc R . . H1"2 H 1.0219 0.5383 0.4208 0.055 Uiso 1 1 calc R . . H1"3 H 0.9379 0.6530 0.3594 0.055 Uiso 1 1 calc R . . C2A C 1.14549(14) 0.37177(13) 0.30019(9) 0.0265(3) Uani 1 1 d . . . C3A C 1.16216(16) 0.29537(13) 0.39072(10) 0.0333(3) Uani 1 1 d . . . C4A C 1.03174(18) 0.27892(15) 0.45286(10) 0.0393(4) Uani 1 1 d . . . H4A H 1.0377 0.2187 0.5049 0.047 Uiso 1 1 calc R . . C5A C 0.90724(17) 0.34477(14) 0.43870(10) 0.0383(4) Uani 1 1 d . . . H5A H 0.8267 0.3325 0.4825 0.046 Uiso 1 1 calc R . . C6A C 0.88551(14) 0.43785(13) 0.35748(9) 0.0294(3) Uani 1 1 d . . . H6A H 0.8708 0.3956 0.3158 0.035 Uiso 1 1 calc R . . C7A C 1.27707(15) 0.40598(14) 0.24399(10) 0.0331(3) Uani 1 1 d . . . H7A1 H 1.2522 0.4882 0.2057 0.040 Uiso 1 1 calc R . . H7A2 H 1.3337 0.4094 0.2815 0.040 Uiso 1 1 calc R . . C8A C 1.24900(14) 0.26779(14) 0.17687(9) 0.0307(3) Uani 1 1 d . . . C9A C 1.20325(17) 0.34425(16) 0.09504(10) 0.0424(4) Uani 1 1 d . . . H9A1 H 1.1689 0.4337 0.1003 0.064 Uiso 1 1 calc R . . H9A2 H 1.1279 0.3196 0.0880 0.064 Uiso 1 1 calc R . . H9A3 H 1.2831 0.3292 0.0436 0.064 Uiso 1 1 calc R . . C10A C 1.30810(16) 0.12894(15) 0.17347(11) 0.0409(4) Uani 1 1 d . . . H10D H 1.3911 0.1129 0.1239 0.061 Uiso 1 1 calc R . . H10E H 1.2370 0.0993 0.1656 0.061 Uiso 1 1 calc R . . H10F H 1.3346 0.0842 0.2287 0.061 Uiso 1 1 calc R . . C11A C 0.63672(15) 0.52466(15) 0.38409(11) 0.0407(4) Uani 1 1 d . . . H11C H 0.6179 0.4626 0.4373 0.049 Uiso 1 1 calc R . . H11D H 0.6417 0.4911 0.3321 0.049 Uiso 1 1 calc R . . C12A C 0.52158(15) 0.64706(15) 0.39153(10) 0.0356(4) Uani 1 1 d . . . C13A C 0.51946(17) 0.73330(16) 0.43791(11) 0.0410(4) Uani 1 1 d . . . H13A H 0.5926 0.7151 0.4663 0.049 Uiso 1 1 calc R . . C14A C 0.41201(18) 0.84604(16) 0.44362(11) 0.0486(4) Uani 1 1 d . . . H14A H 0.4121 0.9051 0.4753 0.058 Uiso 1 1 calc R . . C15A C 0.30493(18) 0.87260(17) 0.40333(12) 0.0518(5) Uani 1 1 d . . . H15A H 0.2311 0.9500 0.4071 0.062 Uiso 1 1 calc R . . C16A C 0.30535(18) 0.78748(18) 0.35805(12) 0.0529(5) Uani 1 1 d . . . H16A H 0.2312 0.8054 0.3306 0.064 Uiso 1 1 calc R . . C17A C 0.41270(17) 0.67561(17) 0.35196(11) 0.0441(4) Uani 1 1 d . . . H17A H 0.4119 0.6172 0.3201 0.053 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 F1 0.0593(6) 0.0549(6) 0.0325(5) 0.0039(4) -0.0198(5) -0.0157(5) F2 0.0371(5) 0.0327(5) 0.0650(6) -0.0053(4) -0.0272(5) 0.0015(4) O1 0.0263(5) 0.0321(6) 0.0420(6) -0.0104(5) -0.0162(5) -0.0013(4) O2 0.0259(5) 0.0239(5) 0.0300(5) -0.0067(4) -0.0015(4) -0.0082(4) O3 0.0352(6) 0.0240(5) 0.0312(6) -0.0038(4) -0.0036(4) -0.0104(4) O4 0.0345(6) 0.0229(5) 0.0330(6) -0.0055(4) -0.0013(4) -0.0070(4) C1 0.0244(7) 0.0266(7) 0.0278(8) -0.0051(6) -0.0086(6) -0.0056(6) C1' 0.0302(8) 0.0343(8) 0.0352(9) -0.0070(7) -0.0024(7) -0.0067(7) C2 0.0244(7) 0.0268(7) 0.0263(7) -0.0037(6) -0.0045(6) -0.0084(6) C3 0.0309(8) 0.0325(8) 0.0344(9) -0.0029(7) -0.0129(7) -0.0033(7) C4 0.0321(8) 0.0423(10) 0.0492(10) -0.0153(8) -0.0199(7) -0.0067(7) C5 0.0305(8) 0.0350(9) 0.0480(10) -0.0178(7) -0.0094(7) -0.0111(7) C6 0.0279(7) 0.0246(7) 0.0308(8) -0.0083(6) -0.0057(6) -0.0055(6) C7 0.0283(8) 0.0260(7) 0.0335(8) -0.0061(6) -0.0040(6) -0.0072(6) C8 0.0378(8) 0.0239(7) 0.0296(8) -0.0036(6) -0.0041(6) -0.0122(7) C9 0.0449(10) 0.0289(8) 0.0411(9) -0.0090(7) 0.0042(7) -0.0089(7) C10 0.0593(11) 0.0373(9) 0.0344(9) -0.0029(7) -0.0139(8) -0.0221(8) C11 0.0361(8) 0.0304(8) 0.0374(9) -0.0017(7) -0.0049(7) -0.0135(7) C12 0.0319(8) 0.0289(8) 0.0251(7) -0.0029(6) -0.0013(6) -0.0123(6) C13 0.0431(9) 0.0354(9) 0.0356(9) -0.0061(7) -0.0076(7) -0.0166(8) C14 0.0533(11) 0.0268(9) 0.0540(11) -0.0082(8) -0.0047(9) -0.0119(8) C15 0.0406(10) 0.0354(10) 0.0622(12) 0.0005(8) -0.0092(9) -0.0015(8) C16 0.0371(10) 0.0520(11) 0.0605(12) -0.0071(9) -0.0163(8) -0.0115(8) C17 0.0388(9) 0.0341(9) 0.0465(10) -0.0087(7) -0.0090(7) -0.0135(7) F1A 0.0423(5) 0.0312(5) 0.0471(6) -0.0021(4) -0.0178(4) 0.0031(4) F2A 0.0585(6) 0.0524(6) 0.0490(6) -0.0111(5) -0.0322(5) -0.0129(5) O1A 0.0351(6) 0.0272(5) 0.0256(5) -0.0002(4) -0.0059(4) -0.0012(5) O2A 0.0250(5) 0.0283(5) 0.0278(5) -0.0088(4) -0.0037(4) -0.0087(4) O3A 0.0244(5) 0.0326(6) 0.0452(6) -0.0139(5) -0.0031(5) -0.0081(4) O4A 0.0255(5) 0.0347(6) 0.0388(6) -0.0111(5) -0.0029(4) -0.0042(5) C1A 0.0296(8) 0.0259(7) 0.0246(7) -0.0033(6) -0.0070(6) -0.0059(6) C1" 0.0396(9) 0.0276(8) 0.0416(9) -0.0097(7) -0.0102(7) -0.0066(7) C2A 0.0281(7) 0.0250(7) 0.0286(8) -0.0065(6) -0.0085(6) -0.0079(6) C3A 0.0371(9) 0.0273(8) 0.0356(8) -0.0069(6) -0.0165(7) -0.0021(7) C4A 0.0521(10) 0.0333(9) 0.0252(8) 0.0003(7) -0.0091(7) -0.0086(8) C5A 0.0405(9) 0.0359(9) 0.0308(8) -0.0029(7) -0.0002(7) -0.0119(8) C6A 0.0286(8) 0.0289(8) 0.0268(8) -0.0072(6) -0.0041(6) -0.0049(6) C7A 0.0289(8) 0.0270(8) 0.0440(9) -0.0106(7) -0.0078(7) -0.0071(6) C8A 0.0242(7) 0.0350(8) 0.0326(8) -0.0116(6) -0.0007(6) -0.0098(6) C9A 0.0406(9) 0.0530(11) 0.0290(9) -0.0100(7) -0.0029(7) -0.0113(8) C10A 0.0330(9) 0.0388(9) 0.0516(10) -0.0213(8) -0.0026(7) -0.0089(7) C11A 0.0302(8) 0.0425(10) 0.0452(10) -0.0068(8) -0.0026(7) -0.0120(7) C12A 0.0286(8) 0.0420(9) 0.0281(8) -0.0023(7) 0.0014(6) -0.0106(7) C13A 0.0364(9) 0.0459(10) 0.0352(9) -0.0040(7) -0.0065(7) -0.0098(8) C14A 0.0479(10) 0.0444(10) 0.0429(10) -0.0090(8) -0.0006(8) -0.0097(9) C15A 0.0386(10) 0.0443(10) 0.0508(11) 0.0015(9) -0.0031(8) -0.0003(8) C16A 0.0344(9) 0.0627(12) 0.0513(11) 0.0013(9) -0.0123(8) -0.0083(9) C17A 0.0356(9) 0.0553(11) 0.0384(9) -0.0081(8) -0.0053(7) -0.0132(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 F1 C3 1.3778(18) . ? F2 C3 1.3686(16) . ? O1 C1 1.4156(16) . ? O2 C2 1.4227(16) . ? O2 C8 1.4344(16) . ? O3 C7 1.4210(16) . ? O3 C8 1.4233(17) . ? O4 C11 1.4220(17) . ? O4 C6 1.4251(16) . ? C1 C1' 1.5197(19) . ? C1 C6 1.5257(19) . ? C1 C2 1.5399(19) . ? C2 C7 1.5288(19) . ? C2 C3 1.5333(19) . ? C3 C4 1.474(2) . ? C4 C5 1.314(2) . ? C5 C6 1.489(2) . ? C8 C9 1.502(2) . ? C8 C10 1.511(2) . ? C11 C12 1.493(2) . ? C12 C13 1.379(2) . ? C12 C17 1.382(2) . ? C13 C14 1.376(2) . ? C14 C15 1.368(2) . ? C15 C16 1.378(2) . ? C16 C17 1.370(2) . ? F1A C3A 1.3698(16) . ? F2A C3A 1.3771(17) . ? O1A C1A 1.4208(16) . ? O2A C2A 1.4227(16) . ? O2A C8A 1.4376(16) . ? O3A C8A 1.4201(17) . ? O3A C7A 1.4210(16) . ? O4A C6A 1.4221(16) . ? O4A C11A 1.4226(18) . ? C1A C1" 1.5175(19) . ? C1A C6A 1.527(2) . ? C1A C2A 1.5391(19) . ? C2A C7A 1.527(2) . ? C2A C3A 1.533(2) . ? C3A C4A 1.471(2) . ? C4A C5A 1.315(2) . ? C5A C6A 1.494(2) . ? C8A C10A 1.505(2) . ? C8A C9A 1.505(2) . ? C11A C12A 1.496(2) . ? C12A C13A 1.379(2) . ? C12A C17A 1.382(2) . ? C13A C14A 1.384(2) . ? C14A C15A 1.377(2) . ? C15A C16A 1.363(3) . ? C16A C17A 1.377(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 O2 C8 110.12(10) . . ? C7 O3 C8 107.40(10) . . ? C11 O4 C6 113.75(10) . . ? O1 C1 C1' 110.48(11) . . ? O1 C1 C6 108.51(11) . . ? C1' C1 C6 112.02(11) . . ? O1 C1 C2 105.88(10) . . ? C1' C1 C2 112.22(11) . . ? C6 C1 C2 107.47(11) . . ? O2 C2 C7 103.90(11) . . ? O2 C2 C3 106.54(11) . . ? C7 C2 C3 112.57(12) . . ? O2 C2 C1 108.92(11) . . ? C7 C2 C1 114.26(11) . . ? C3 C2 C1 110.13(11) . . ? F2 C3 F1 103.47(11) . . ? F2 C3 C4 109.69(12) . . ? F1 C3 C4 109.59(12) . . ? F2 C3 C2 109.13(12) . . ? F1 C3 C2 109.70(12) . . ? C4 C3 C2 114.66(12) . . ? C5 C4 C3 121.89(14) . . ? C4 C5 C6 123.81(14) . . ? O4 C6 C5 111.72(11) . . ? O4 C6 C1 107.67(11) . . ? C5 C6 C1 112.58(12) . . ? O3 C7 C2 103.52(11) . . ? O3 C8 O2 105.19(11) . . ? O3 C8 C9 108.25(12) . . ? O2 C8 C9 109.18(12) . . ? O3 C8 C10 111.31(12) . . ? O2 C8 C10 109.18(11) . . ? C9 C8 C10 113.38(13) . . ? O4 C11 C12 109.31(11) . . ? C13 C12 C17 118.72(14) . . ? C13 C12 C11 121.18(14) . . ? C17 C12 C11 120.03(13) . . ? C14 C13 C12 120.73(15) . . ? C15 C14 C13 120.18(16) . . ? C14 C15 C16 119.51(16) . . ? C17 C16 C15 120.42(17) . . ? C16 C17 C12 120.43(15) . . ? C2A O2A C8A 110.16(10) . . ? C8A O3A C7A 107.09(10) . . ? C6A O4A C11A 113.65(11) . . ? O1A C1A C1" 110.07(11) . . ? O1A C1A C6A 108.52(11) . . ? C1" C1A C6A 111.60(12) . . ? O1A C1A C2A 105.90(11) . . ? C1" C1A C2A 111.94(12) . . ? C6A C1A C2A 108.59(11) . . ? O2A C2A C7A 103.69(11) . . ? O2A C2A C3A 106.30(11) . . ? C7A C2A C3A 113.20(12) . . ? O2A C2A C1A 109.35(11) . . ? C7A C2A C1A 113.64(11) . . ? C3A C2A C1A 110.14(11) . . ? F1A C3A F2A 103.34(11) . . ? F1A C3A C4A 110.00(12) . . ? F2A C3A C4A 109.17(12) . . ? F1A C3A C2A 109.15(12) . . ? F2A C3A C2A 109.39(12) . . ? C4A C3A C2A 115.14(12) . . ? C5A C4A C3A 122.15(14) . . ? C4A C5A C6A 123.57(14) . . ? O4A C6A C5A 112.54(11) . . ? O4A C6A C1A 107.16(11) . . ? C5A C6A C1A 112.55(12) . . ? O3A C7A C2A 103.81(11) . . ? O3A C8A O2A 104.77(10) . . ? O3A C8A C10A 108.41(12) . . ? O2A C8A C10A 109.21(12) . . ? O3A C8A C9A 111.15(12) . . ? O2A C8A C9A 109.69(12) . . ? C10A C8A C9A 113.25(13) . . ? O4A C11A C12A 108.70(13) . . ? C13A C12A C17A 118.25(15) . . ? C13A C12A C11A 121.85(14) . . ? C17A C12A C11A 119.89(15) . . ? C12A C13A C14A 120.77(16) . . ? C15A C14A C13A 119.92(17) . . ? C16A C15A C14A 119.77(17) . . ? C15A C16A C17A 120.31(17) . . ? C16A C17A C12A 120.99(17) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.254 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.036 #===END