# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_screw3 _database_code_CSD 161707 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Nenajdenko, Valentine' 'Balenkova, Elisabeth S.' 'Krasovsky, Arkady L.' 'Pissarev, Serge A.' _publ_contact_author_name 'Dr Valentine Nenajdenko' _publ_contact_author_address ; Department of Chemistry Moscow State University 119899, Leninskie Gory, Moscow, Rus Moscow 119899 RUSSIAN FEDERATION ; _publ_contact_author_email nen@acylium.chem.msu.ru _publ_requested_journal 'Perkin 1' _publ_section_title ; Beta-Trifluoroacetyl Phenylvinylsulfoxide - Synthesis, Diels-Alder Reaction and Computational Study ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 F3 O3 S' _chemical_formula_weight 266.23 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.913(4) _cell_length_b 5.1380(10) _cell_length_c 22.413(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.92(3) _cell_angle_gamma 90.00 _cell_volume 2292.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12.2 _cell_measurement_theta_max 13.5 _exptl_crystal_description prizm _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator filter _diffrn_measurement_device_type CAD4 _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% .2 _diffrn_reflns_number 1219 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1181 _reflns_number_gt 1181 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+1.1611P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1181 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.58062(4) 0.52284(13) 0.34648(3) 0.0474(3) Uani 1 1 d . . . F1 F 0.72185(10) 0.1857(5) 0.16118(10) 0.0837(7) Uani 1 1 d . . . F2 F 0.70750(10) -0.0974(4) 0.22898(9) 0.0766(6) Uani 1 1 d . . . F3 F 0.67784(10) -0.1831(4) 0.13894(10) 0.0809(6) Uani 1 1 d . . . O1 O 0.58926(13) 0.2151(5) 0.13767(9) 0.0622(6) Uani 1 1 d . . . O2 O 0.57011(11) -0.0946(4) 0.21020(10) 0.0533(6) Uani 1 1 d . . . O3 O 0.50821(11) 0.5881(4) 0.35890(9) 0.0571(6) Uani 1 1 d . . . C1 C 0.68014(16) 0.0046(6) 0.18002(14) 0.0566(7) Uani 1 1 d . . . C2 C 0.60989(14) 0.1109(5) 0.19173(11) 0.0432(7) Uani 1 1 d . . . C3 C 0.61288(15) 0.3091(5) 0.24140(11) 0.0437(7) Uani 1 1 d . . . C4 C 0.57841(15) 0.2833(5) 0.29013(12) 0.0432(6) Uani 1 1 d . . . C5 C 0.60637(14) 0.3142(6) 0.40623(12) 0.0467(7) Uani 1 1 d . . . C6 C 0.66430(18) 0.1710(9) 0.40222(17) 0.0755(11) Uani 1 1 d . . . C7 C 0.6835(2) 0.0131(10) 0.44941(19) 0.0938(14) Uani 1 1 d . . . C8 C 0.6465(2) -0.0018(9) 0.49884(18) 0.0888(13) Uani 1 1 d . . . C9 C 0.5892(3) 0.1395(12) 0.50206(18) 0.1099(18) Uani 1 1 d . . . C10 C 0.5685(2) 0.2985(10) 0.45582(15) 0.0877(14) Uani 1 1 d . . . H1 H 0.5628(19) 0.327(7) 0.1419(16) 0.065(12) Uiso 1 1 d . . . H2 H 0.5537(17) -0.165(7) 0.1855(16) 0.058(11) Uiso 1 1 d . . . H3 H 0.6375(16) 0.460(6) 0.2351(13) 0.055(8) Uiso 1 1 d . . . H4 H 0.5516(15) 0.149(6) 0.2965(13) 0.051(8) Uiso 1 1 d . . . H6 H 0.689(2) 0.179(8) 0.365(2) 0.101(13) Uiso 1 1 d . . . H7 H 0.723(3) -0.063(10) 0.448(2) 0.117(17) Uiso 1 1 d . . . H8 H 0.659(2) -0.105(10) 0.534(2) 0.114(15) Uiso 1 1 d . . . H9 H 0.561(3) 0.095(12) 0.536(3) 0.15(2) Uiso 1 1 d . . . H10 H 0.534(3) 0.411(10) 0.459(2) 0.127(18) Uiso 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 S1 0.0614(5) 0.0405(4) 0.0400(4) -0.0044(3) -0.0059(3) -0.0011(3) F1 0.0686(13) 0.0883(15) 0.0951(15) 0.0045(12) 0.0265(11) -0.0191(11) F2 0.0647(12) 0.0798(13) 0.0848(14) 0.0090(11) -0.0137(10) 0.0129(10) F3 0.0782(13) 0.0806(14) 0.0842(14) -0.0301(11) 0.0120(11) 0.0122(11) O1 0.0844(17) 0.0662(14) 0.0359(10) 0.0009(10) -0.0037(10) 0.0142(14) O2 0.0613(14) 0.0494(12) 0.0491(12) -0.0114(10) 0.0026(10) -0.0159(10) O3 0.0668(14) 0.0530(12) 0.0513(11) -0.0068(9) -0.0093(10) 0.0158(10) C1 0.0575(18) 0.0537(18) 0.0588(17) -0.0012(15) 0.0067(14) -0.0021(15) C2 0.0548(18) 0.0382(14) 0.0366(13) 0.0016(11) 0.0010(12) -0.0020(12) C3 0.0551(17) 0.0347(14) 0.0411(15) 0.0037(11) -0.0033(13) -0.0039(13) C4 0.0533(16) 0.0394(15) 0.0367(14) -0.0010(11) -0.0050(12) -0.0061(13) C5 0.0491(16) 0.0528(17) 0.0382(13) -0.0050(12) -0.0048(12) 0.0038(14) C6 0.056(2) 0.111(3) 0.059(2) 0.017(2) 0.0027(17) 0.019(2) C7 0.085(3) 0.124(4) 0.072(3) 0.013(2) -0.006(2) 0.049(3) C8 0.104(3) 0.109(3) 0.054(2) 0.016(2) -0.011(2) 0.033(3) C9 0.114(4) 0.168(5) 0.049(2) 0.032(3) 0.017(2) 0.044(4) C10 0.087(3) 0.133(4) 0.0436(18) 0.012(2) 0.0122(18) 0.048(3) _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 O3 1.511(2) . ? S1 C4 1.764(3) . ? S1 C5 1.784(3) . ? F1 C1 1.321(4) . ? F2 C1 1.326(4) . ? F3 C1 1.333(4) . ? O1 C2 1.381(3) . ? O2 C2 1.387(3) . ? C1 C2 1.528(4) . ? C2 C3 1.509(4) . ? C3 C4 1.306(4) . ? C5 C10 1.356(5) . ? C5 C6 1.372(5) . ? C6 C7 1.382(5) . ? C7 C8 1.343(6) . ? C8 C9 1.356(6) . ? C9 C10 1.378(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 O3 S1 C4 105.90(13) . . ? O3 S1 C5 105.00(13) . . ? C4 S1 C5 96.99(13) . . ? F1 C1 F2 106.9(3) . . ? F1 C1 F3 107.7(2) . . ? F2 C1 F3 107.1(3) . . ? F1 C1 C2 112.7(3) . . ? F2 C1 C2 111.4(2) . . ? F3 C1 C2 110.8(3) . . ? O1 C2 O2 113.2(2) . . ? O1 C2 C3 113.2(2) . . ? O2 C2 C3 108.0(2) . . ? O1 C2 C1 104.4(2) . . ? O2 C2 C1 107.9(2) . . ? C3 C2 C1 110.0(2) . . ? C4 C3 C2 122.2(3) . . ? C3 C4 S1 121.4(2) . . ? C10 C5 C6 120.1(3) . . ? C10 C5 S1 119.6(3) . . ? C6 C5 S1 120.3(2) . . ? C5 C6 C7 119.1(4) . . ? C8 C7 C6 121.1(4) . . ? C7 C8 C9 119.2(4) . . ? C8 C9 C10 121.3(4) . . ? C5 C10 C9 119.2(4) . . ? _diffrn_measured_fraction_theta_max 0.587 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.587 _refine_diff_density_max 0.218 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.049