data_3am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H15 F3 O2 S' _chemical_formula_weight 412.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 5.591(2) _cell_length_b 16.262(6) _cell_length_c 21.370(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.569(8) _cell_angle_gamma 90.00 _cell_volume 1942.4(13) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1077 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 19.11 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 11432 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4225 _reflns_number_gt 2105 _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^)+(0.1193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4225 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1576 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2336 _refine_ls_wR_factor_gt 0.1923 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 F1 F -0.1113(10) -0.07278(18) 0.3589(2) 0.178(2) Uani 1 1 d . . . F2 F -0.2386(10) -0.0604(2) 0.4503(3) 0.183(2) Uani 1 1 d . . . F3 F 0.1181(9) -0.0561(2) 0.4342(2) 0.1530(16) Uani 1 1 d . . . O1 O -0.4476(6) 0.29355(19) 0.30081(14) 0.0811(9) Uani 1 1 d . . . O2 O 0.6748(5) 0.2987(2) 0.60323(14) 0.0749(9) Uani 1 1 d . . . C1 C -0.1220(6) 0.2282(2) 0.38310(17) 0.0476(9) Uani 1 1 d . . . C2 C -0.1371(6) 0.3193(2) 0.37376(17) 0.0476(9) Uani 1 1 d . . . C3 C 0.1830(6) 0.3493(2) 0.45808(17) 0.0457(9) Uani 1 1 d . . . C4 C 0.0087(6) 0.3722(2) 0.40750(17) 0.0492(9) Uani 1 1 d . . . C5 C -0.3193(7) 0.3457(3) 0.32746(18) 0.0586(10) Uani 1 1 d . . . C6 C -0.3479(7) 0.4340(2) 0.31185(18) 0.0564(10) Uani 1 1 d . . . C7 C -0.3049(7) 0.1867(2) 0.41256(18) 0.0551(10) Uani 1 1 d . . . H7 H -0.4374 0.2156 0.4260 0.066 Uiso 1 1 calc R . . C8 C -0.2909(8) 0.1028(3) 0.4219(2) 0.0616(11) Uani 1 1 d . . . H8 H -0.4121 0.0759 0.4428 0.074 Uiso 1 1 calc R . . C9 C 0.1351(7) 0.2875(2) 0.50181(18) 0.0540(10) Uani 1 1 d . . . H9 H -0.0073 0.2582 0.4979 0.065 Uiso 1 1 calc R . . C10 C -0.1018(9) 0.0589(2) 0.4010(2) 0.0619(11) Uani 1 1 d . . . C11 C 0.3971(6) 0.3927(2) 0.46716(18) 0.0508(10) Uani 1 1 d . . . H11 H 0.4339 0.4346 0.4395 0.061 Uiso 1 1 calc R . . C12 C -0.2061(8) 0.4956(2) 0.33824(18) 0.0580(10) Uani 1 1 d . . . C13 C 0.5061(7) 0.3123(3) 0.55717(18) 0.0566(11) Uani 1 1 d . . . C14 C 0.0689(7) 0.1843(3) 0.36153(19) 0.0615(11) Uani 1 1 d . . . H14 H 0.1912 0.2113 0.3412 0.074 Uiso 1 1 calc R . . C15 C 0.0794(8) 0.0988(3) 0.3701(2) 0.0688(12) Uani 1 1 d . . . H15 H 0.2078 0.0691 0.3551 0.083 Uiso 1 1 calc R . . C16 C 0.2931(7) 0.2692(2) 0.55041(18) 0.0557(10) Uani 1 1 d . . . H16 H 0.2569 0.2279 0.5787 0.067 Uiso 1 1 calc R . . C17 C 0.5532(7) 0.3753(2) 0.51537(19) 0.0548(10) Uani 1 1 d . . . H17 H 0.6929 0.4060 0.5204 0.066 Uiso 1 1 calc R . . C18 C -0.5254(9) 0.4563(3) 0.2675(2) 0.0765(13) Uani 1 1 d . . . H18 H -0.6224 0.4159 0.2493 0.092 Uiso 1 1 calc R . . C19 C -0.2381(9) 0.5774(3) 0.3193(2) 0.0768(14) Uani 1 1 d . . . H19 H -0.1413 0.6184 0.3368 0.092 Uiso 1 1 calc R . . C20 C -0.5574(11) 0.5363(4) 0.2509(2) 0.0910(16) Uani 1 1 d . . . H20 H -0.6799 0.5504 0.2226 0.109 Uiso 1 1 calc R . . C21 C -0.0859(12) -0.0315(3) 0.4086(3) 0.0974(18) Uani 1 1 d . . . C22 C -0.4082(10) 0.5973(3) 0.2759(2) 0.0881(16) Uani 1 1 d . . . H22 H -0.4258 0.6515 0.2627 0.106 Uiso 1 1 calc R . . C23 C 0.6443(10) 0.2288(3) 0.6431(2) 0.0950(16) Uani 1 1 d . . . H23A H 0.4968 0.2341 0.6647 0.143 Uiso 1 1 calc R . . H23B H 0.7753 0.2259 0.6730 0.143 Uiso 1 1 calc R . . H23C H 0.6403 0.1796 0.6182 0.143 Uiso 1 1 calc R . . S1 S 0.0046(2) 0.47839(6) 0.39765(5) 0.0632(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.342(7) 0.0446(17) 0.140(3) -0.0225(19) -0.127(4) 0.019(3) F2 0.247(6) 0.054(2) 0.250(5) 0.028(3) 0.058(5) 0.000(3) F3 0.198(4) 0.074(2) 0.182(4) 0.001(2) -0.084(3) 0.045(2) O1 0.097(2) 0.066(2) 0.078(2) 0.0001(17) -0.0402(17) -0.0134(18) O2 0.0677(18) 0.080(2) 0.076(2) -0.0034(17) -0.0227(16) 0.0087(16) C1 0.049(2) 0.044(2) 0.050(2) -0.0083(17) -0.0079(17) -0.0037(18) C2 0.051(2) 0.041(2) 0.050(2) -0.0045(17) -0.0031(17) -0.0023(17) C3 0.048(2) 0.0351(18) 0.054(2) -0.0085(17) -0.0030(17) -0.0005(17) C4 0.054(2) 0.037(2) 0.057(2) 0.0007(17) -0.0022(18) -0.0026(18) C5 0.064(2) 0.053(2) 0.058(2) -0.007(2) -0.014(2) -0.003(2) C6 0.070(3) 0.049(2) 0.050(2) 0.0041(19) -0.007(2) 0.003(2) C7 0.053(2) 0.043(2) 0.069(3) -0.0034(19) -0.011(2) 0.0022(19) C8 0.067(3) 0.047(2) 0.070(3) 0.002(2) -0.017(2) -0.011(2) C9 0.052(2) 0.050(2) 0.060(2) -0.005(2) -0.0063(19) -0.0092(19) C10 0.075(3) 0.038(2) 0.071(3) -0.005(2) -0.025(2) 0.004(2) C11 0.055(2) 0.038(2) 0.059(2) -0.0048(18) -0.0012(19) -0.0062(18) C12 0.080(3) 0.041(2) 0.053(2) 0.0003(19) 0.001(2) 0.004(2) C13 0.054(2) 0.056(2) 0.059(3) -0.009(2) -0.012(2) 0.008(2) C14 0.056(2) 0.057(3) 0.072(3) -0.011(2) -0.003(2) 0.001(2) C15 0.064(3) 0.056(3) 0.085(3) -0.016(2) -0.017(2) 0.021(2) C16 0.065(2) 0.047(2) 0.055(2) 0.0008(19) -0.0074(19) 0.000(2) C17 0.048(2) 0.050(2) 0.065(3) -0.013(2) -0.0079(19) -0.0056(19) C18 0.094(3) 0.073(3) 0.061(3) 0.003(2) -0.021(2) 0.014(3) C19 0.115(4) 0.047(3) 0.069(3) 0.000(2) -0.005(3) 0.007(3) C20 0.118(4) 0.092(4) 0.062(3) 0.005(3) -0.024(3) 0.027(4) C21 0.120(5) 0.051(3) 0.119(5) 0.008(3) -0.042(4) -0.002(3) C22 0.135(5) 0.060(3) 0.069(3) 0.009(3) -0.004(3) 0.028(3) C23 0.117(4) 0.077(4) 0.090(4) 0.006(3) -0.030(3) 0.020(3) S1 0.0791(8) 0.0371(6) 0.0722(8) -0.0014(5) -0.0176(6) -0.0042(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C21 1.262(6) . ? F2 C21 1.336(8) . ? F3 C21 1.314(6) . ? O1 C5 1.239(4) . ? O2 C13 1.363(4) . ? O2 C23 1.433(6) . ? C1 C14 1.374(5) . ? C1 C7 1.390(5) . ? C1 C2 1.498(5) . ? C2 C4 1.376(5) . ? C2 C5 1.465(5) . ? C3 C11 1.398(5) . ? C3 C9 1.403(5) . ? C3 C4 1.483(5) . ? C4 S1 1.739(4) . ? C5 C6 1.482(5) . ? C6 C12 1.388(6) . ? C6 C18 1.401(6) . ? C7 C8 1.381(5) . ? C7 H7 0.9300 . ? C8 C10 1.361(6) . ? C8 H8 0.9300 . ? C9 C16 1.378(5) . ? C9 H9 0.9300 . ? C10 C15 1.386(6) . ? C10 C21 1.482(7) . ? C11 C17 1.362(5) . ? C11 H11 0.9300 . ? C12 C19 1.401(6) . ? C12 S1 1.731(4) . ? C13 C16 1.386(5) . ? C13 C17 1.390(5) . ? C14 C15 1.402(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C20 1.359(7) . ? C18 H18 0.9300 . ? C19 C22 1.350(6) . ? C19 H19 0.9300 . ? C20 C22 1.394(7) . ? C20 H20 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 O2 C23 117.8(3) . . ? C14 C1 C7 119.2(4) . . ? C14 C1 C2 120.7(4) . . ? C7 C1 C2 120.1(3) . . ? C4 C2 C5 124.2(3) . . ? C4 C2 C1 121.3(3) . . ? C5 C2 C1 114.5(3) . . ? C11 C3 C9 116.6(3) . . ? C11 C3 C4 121.1(3) . . ? C9 C3 C4 122.1(3) . . ? C2 C4 C3 126.3(3) . . ? C2 C4 S1 123.5(3) . . ? C3 C4 S1 110.1(2) . . ? O1 C5 C2 119.6(4) . . ? O1 C5 C6 120.1(4) . . ? C2 C5 C6 120.3(3) . . ? C12 C6 C18 118.3(4) . . ? C12 C6 C5 123.5(4) . . ? C18 C6 C5 118.3(4) . . ? C8 C7 C1 120.4(4) . . ? C8 C7 H7 119.8 . . ? C1 C7 H7 119.8 . . ? C10 C8 C7 120.8(4) . . ? C10 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C16 C9 C3 121.8(3) . . ? C16 C9 H9 119.1 . . ? C3 C9 H9 119.1 . . ? C8 C10 C15 119.7(4) . . ? C8 C10 C21 121.9(5) . . ? C15 C10 C21 118.3(5) . . ? C17 C11 C3 121.9(4) . . ? C17 C11 H11 119.0 . . ? C3 C11 H11 119.0 . . ? C6 C12 C19 120.1(4) . . ? C6 C12 S1 123.4(3) . . ? C19 C12 S1 116.4(3) . . ? O2 C13 C16 124.7(4) . . ? O2 C13 C17 116.4(4) . . ? C16 C13 C17 118.9(3) . . ? C1 C14 C15 120.1(4) . . ? C1 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 119.8(4) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C9 C16 C13 120.0(4) . . ? C9 C16 H16 120.0 . . ? C13 C16 H16 120.0 . . ? C11 C17 C13 120.7(4) . . ? C11 C17 H17 119.7 . . ? C13 C17 H17 119.7 . . ? C20 C18 C6 120.7(5) . . ? C20 C18 H18 119.6 . . ? C6 C18 H18 119.6 . . ? C22 C19 C12 120.5(5) . . ? C22 C19 H19 119.7 . . ? C12 C19 H19 119.7 . . ? C18 C20 C22 120.5(5) . . ? C18 C20 H20 119.7 . . ? C22 C20 H20 119.7 . . ? F1 C21 F3 105.4(6) . . ? F1 C21 F2 108.4(5) . . ? F3 C21 F2 100.3(5) . . ? F1 C21 C10 115.5(5) . . ? F3 C21 C10 113.4(5) . . ? F2 C21 C10 112.6(6) . . ? C19 C22 C20 119.8(5) . . ? C19 C22 H22 120.1 . . ? C20 C22 H22 120.1 . . ? O2 C23 H23A 109.5 . . ? O2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 S1 C4 104.82(18) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.625 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.064