Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_total _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Elena Roversi' 'Rosario Scopelliti' 'Euro Solari' 'Raphael Estoppey' 'Pierre Vogel' 'Pedro Brana' 'Bibiana Menendez' 'Sordo, Jose Angel' _audit_creation_method SHELXL-97 _publ_contact_author_name 'Pierre Vogel' _publ_contact_author_address ; Prof Pierre Vogel Section de chimie Universite de Lausanne BCH Lausanne-Dorigny CH-1015 SWITZERLAND ; _publ_contact_author_email 'pierre.vogel@ico.unil.ch' _publ_contact_author_fax '+4121 692 3975' _publ_contact_author_phone '+4121 692 3971' _publ_section_title ; The Hetero-Diels-Alder Addition of Sulfur Dioxide: Structure of the First Crystalline Sultine. Quantum Calculations on the Conformations of 6-Fluoro-3, 6-dihydro, 2-oxathiin-2-oxides. ; data_5 _database_code_CSD 157490 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 F O2 S' _chemical_formula_weight 238.27 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)/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 7.8271(9) _cell_length_b 13.982(2) _cell_length_c 10.1237(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.577(12) _cell_angle_gamma 90.00 _cell_volume 1061.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.299 _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 143(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 'KUMA CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5521 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1795 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, 1.6.7, 2000' _computing_cell_refinement 'CrysAlis RED, 1.6.7, 2000' _computing_data_reduction 'CrysAlis RED' _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^)+(0.0521P)^2^+1.5444P] 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 SHELXL _refine_ls_extinction_coef 0.004(3) _refine_ls_extinction_expression 'Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1795 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 -0.02353(9) 0.09167(5) 0.16418(7) 0.0252(3) Uani 1 1 d . . . O1 O 0.1337(2) 0.17496(13) 0.22832(19) 0.0252(5) Uani 1 1 d . . . O2 O -0.1089(3) 0.12661(17) 0.0233(2) 0.0377(6) Uani 1 1 d . . . C1 C 0.2345(3) 0.15812(19) 0.3661(3) 0.0235(6) Uani 1 1 d . . . H1 H 0.3088 0.2161 0.4003 0.028 Uiso 1 1 calc R . . F1 F 0.3502(2) 0.08104(12) 0.36289(17) 0.0313(4) Uani 1 1 d . . . C2 C 0.1247(3) 0.13720(17) 0.4636(3) 0.0196(6) Uani 1 1 d . . . C3 C -0.0550(3) 0.13180(17) 0.4201(3) 0.0207(6) Uani 1 1 d . . . C4 C -0.1611(3) 0.12977(19) 0.2692(3) 0.0254(6) Uani 1 1 d . . . H4A H -0.2089 0.1944 0.2401 0.031 Uiso 1 1 calc R . . H4B H -0.2632 0.0854 0.2563 0.031 Uiso 1 1 calc R . . C5 C -0.1649(3) 0.12392(19) 0.5209(3) 0.0238(6) Uani 1 1 d . . . H5A H -0.1882 0.0556 0.5348 0.029 Uiso 1 1 calc R . . H5B H -0.2812 0.1559 0.4814 0.029 Uiso 1 1 calc R . . C6 C -0.0712(4) 0.1693(2) 0.6603(3) 0.0264(6) Uani 1 1 d . . . H6A H -0.0792 0.2398 0.6517 0.032 Uiso 1 1 calc R . . H6B H -0.1326 0.1496 0.7289 0.032 Uiso 1 1 calc R . . C7 C 0.1234(3) 0.13998(18) 0.7106(3) 0.0227(6) Uani 1 1 d . . . C8 C 0.2205(3) 0.12779(17) 0.6139(3) 0.0202(6) Uani 1 1 d . . . C9 C 0.4036(4) 0.10545(19) 0.6614(3) 0.0249(6) Uani 1 1 d . . . H9 H 0.4702 0.0971 0.5971 0.030 Uiso 1 1 calc R . . C10 C 0.4880(4) 0.0956(2) 0.8028(3) 0.0306(7) Uani 1 1 d . . . H10 H 0.6114 0.0805 0.8342 0.037 Uiso 1 1 calc R . . C11 C 0.3910(4) 0.1078(2) 0.8972(3) 0.0319(7) Uani 1 1 d . . . H11 H 0.4482 0.1009 0.9930 0.038 Uiso 1 1 calc R . . C12 C 0.2095(4) 0.13004(19) 0.8515(3) 0.0289(7) Uani 1 1 d . . . H12 H 0.1441 0.1385 0.9166 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 0.0225(4) 0.0287(4) 0.0232(4) -0.0008(3) 0.0045(3) -0.0016(3) O1 0.0251(10) 0.0272(10) 0.0234(10) 0.0026(7) 0.0073(8) -0.0040(7) O2 0.0307(11) 0.0553(14) 0.0234(11) 0.0049(9) 0.0019(9) -0.0036(10) C1 0.0203(12) 0.0261(13) 0.0243(14) -0.0006(10) 0.0065(11) -0.0011(10) F1 0.0227(8) 0.0417(10) 0.0311(9) 0.0006(7) 0.0102(7) 0.0080(7) C2 0.0184(12) 0.0186(12) 0.0225(13) -0.0009(10) 0.0070(10) 0.0000(9) C3 0.0179(12) 0.0171(12) 0.0277(14) 0.0018(10) 0.0071(11) 0.0008(10) C4 0.0182(12) 0.0286(14) 0.0281(15) 0.0021(11) 0.0044(11) 0.0015(10) C5 0.0171(12) 0.0269(13) 0.0298(15) 0.0015(11) 0.0106(11) 0.0004(10) C6 0.0262(14) 0.0254(13) 0.0310(15) -0.0009(11) 0.0135(12) 0.0019(11) C7 0.0241(13) 0.0184(12) 0.0261(14) -0.0042(10) 0.0078(11) -0.0030(10) C8 0.0208(12) 0.0166(12) 0.0235(14) -0.0021(10) 0.0069(11) -0.0030(10) C9 0.0212(13) 0.0261(13) 0.0259(15) -0.0014(10) 0.0044(11) -0.0040(11) C10 0.0254(14) 0.0312(15) 0.0300(16) 0.0008(12) -0.0004(12) -0.0022(11) C11 0.0399(17) 0.0300(14) 0.0220(14) -0.0007(11) 0.0030(13) -0.0055(12) C12 0.0383(16) 0.0235(14) 0.0265(15) -0.0019(11) 0.0119(13) -0.0045(12) _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 O2 1.475(2) . ? S1 O1 1.6840(19) . ? S1 C4 1.796(3) . ? O1 C1 1.413(3) . ? C1 F1 1.414(3) . ? C1 C2 1.511(4) . ? C2 C3 1.351(3) . ? C2 C8 1.498(3) . ? C3 C5 1.514(4) . ? C3 C4 1.517(4) . ? C5 C6 1.530(4) . ? C6 C7 1.519(4) . ? C7 C12 1.400(4) . ? C7 C8 1.410(4) . ? C8 C9 1.411(4) . ? C9 C10 1.403(4) . ? C10 C11 1.390(5) . ? C11 C12 1.398(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 102.91(11) . . ? O2 S1 C4 106.94(13) . . ? O1 S1 C4 93.57(11) . . ? C1 O1 S1 113.98(16) . . ? O1 C1 F1 106.6(2) . . ? O1 C1 C2 114.6(2) . . ? F1 C1 C2 110.8(2) . . ? C3 C2 C8 119.9(2) . . ? C3 C2 C1 122.1(2) . . ? C8 C2 C1 117.9(2) . . ? C2 C3 C5 121.6(2) . . ? C2 C3 C4 123.3(2) . . ? C5 C3 C4 115.1(2) . . ? C3 C4 S1 110.68(18) . . ? C3 C5 C6 112.1(2) . . ? C7 C6 C5 111.6(2) . . ? C12 C7 C8 119.8(2) . . ? C12 C7 C6 120.9(3) . . ? C8 C7 C6 119.2(2) . . ? C7 C8 C9 119.1(2) . . ? C7 C8 C2 118.8(2) . . ? C9 C8 C2 122.0(2) . . ? C10 C9 C8 120.4(3) . . ? C11 C10 C9 119.9(3) . . ? C10 C11 C12 120.2(3) . . ? C11 C12 C7 120.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 O1 C1 179.11(18) . . . . ? C4 S1 O1 C1 70.82(19) . . . . ? S1 O1 C1 F1 73.4(2) . . . . ? S1 O1 C1 C2 -49.5(3) . . . . ? O1 C1 C2 C3 2.3(4) . . . . ? F1 C1 C2 C3 -118.3(3) . . . . ? O1 C1 C2 C8 -174.3(2) . . . . ? F1 C1 C2 C8 65.1(3) . . . . ? C8 C2 C3 C5 4.8(4) . . . . ? C1 C2 C3 C5 -171.8(2) . . . . ? C8 C2 C3 C4 -173.1(2) . . . . ? C1 C2 C3 C4 10.4(4) . . . . ? C2 C3 C4 S1 21.2(3) . . . . ? C5 C3 C4 S1 -156.84(18) . . . . ? O2 S1 C4 C3 -158.32(18) . . . . ? O1 S1 C4 C3 -53.67(19) . . . . ? C2 C3 C5 C6 27.4(3) . . . . ? C4 C3 C5 C6 -154.6(2) . . . . ? C3 C5 C6 C7 -45.7(3) . . . . ? C5 C6 C7 C12 -147.7(2) . . . . ? C5 C6 C7 C8 35.8(3) . . . . ? C12 C7 C8 C9 0.1(4) . . . . ? C6 C7 C8 C9 176.7(2) . . . . ? C12 C7 C8 C2 179.0(2) . . . . ? C6 C7 C8 C2 -4.4(3) . . . . ? C3 C2 C8 C7 -17.4(3) . . . . ? C1 C2 C8 C7 159.2(2) . . . . ? C3 C2 C8 C9 161.4(2) . . . . ? C1 C2 C8 C9 -21.9(3) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C2 C8 C9 C10 -178.9(2) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C10 C11 C12 C7 0.2(4) . . . . ? C8 C7 C12 C11 -0.2(4) . . . . ? C6 C7 C12 C11 -176.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.284 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.067