Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;Structure, Bonding, Aromaticity and Reactivity of Roesky's Sulfoxide ; loop_ _publ_author_name 'Frank Blockhuys' 'C.Van Alsenoy' 'Vit Matuska' A.Slawin 'Karla Tersago' ; J.Woollins ; _publ_contact_author_name 'Frank Blockhuys' _publ_contact_author_email FRANK.BLOCKHUYS@UA.AC.BE # Attachment 'article.cif' data_vmdw2 _database_code_depnum_ccdc_archive 'CCDC 646592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'N2 O S3' _chemical_formula_sum 'N2 O S3' _chemical_formula_weight 140.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' 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 Cc 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' _cell_length_a 7.617(5) _cell_length_b 9.230(6) _cell_length_c 7.050(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.920(6) _cell_angle_gamma 90.00 _cell_volume 445.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 469 _cell_measurement_theta_min 3.1929 _cell_measurement_theta_max 36.3168 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 1.497 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3792 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 6.98 _diffrn_reflns_theta_max 36.62 _reflns_number_total 993 _reflns_number_gt 953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0394P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(10) _refine_ls_number_reflns 993 _refine_ls_number_parameters 56 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0537 _refine_ls_wR_factor_gt 0.0533 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _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 0.85274(5) -0.41353(3) 0.20852(6) 0.01522(9) Uani 1 1 d . . . O1 O 0.6964(2) -0.47701(14) 0.0168(3) 0.0222(3) Uani 1 1 d . . . S2 S 0.70366(6) -0.25753(4) 0.32809(7) 0.01823(10) Uani 1 1 d . . . N3 N 0.7217(3) -0.11501(14) 0.1994(3) 0.0212(3) Uani 1 1 d . . . S4 S 0.86797(7) -0.12615(4) 0.09793(8) 0.02218(11) Uani 1 1 d . . . N5 N 0.9605(2) -0.28326(17) 0.1395(3) 0.0213(3) 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 S1 0.01545(16) 0.01408(14) 0.0165(2) -0.00036(11) 0.00734(16) 0.00119(11) O1 0.0225(6) 0.0218(5) 0.0216(8) -0.0063(4) 0.0088(6) -0.0023(4) S2 0.02048(19) 0.01841(14) 0.0187(2) -0.00120(13) 0.01123(19) 0.00228(12) N3 0.0202(6) 0.0146(5) 0.0240(10) 0.0000(5) 0.0053(7) 0.0022(4) S4 0.01977(19) 0.01970(16) 0.0243(3) 0.00643(15) 0.00704(19) -0.00375(13) N5 0.0180(7) 0.0244(5) 0.0248(10) 0.0038(6) 0.0125(7) 0.0003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4769(17) . ? S1 N5 1.6447(16) . ? S1 S2 2.2158(9) . ? S2 N3 1.6372(18) . ? N3 S4 1.5689(19) . ? S4 N5 1.5827(18) . ? 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 O1 S1 N5 109.05(10) . . ? O1 S1 S2 105.30(7) . . ? N5 S1 S2 92.43(7) . . ? N3 S2 S1 97.49(7) . . ? S4 N3 S2 116.63(9) . . ? N3 S4 N5 108.85(8) . . ? S4 N5 S1 119.03(10) . . ? 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 O1 S1 S2 N3 -90.40(10) . . . . ? N5 S1 S2 N3 20.11(10) . . . . ? S1 S2 N3 S4 -14.31(12) . . . . ? S2 N3 S4 N5 2.39(15) . . . . ? N3 S4 N5 S1 17.43(15) . . . . ? O1 S1 N5 S4 84.44(14) . . . . ? S2 S1 N5 S4 -22.66(12) . . . . ? _diffrn_measured_fraction_theta_max 0.704 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.696 _refine_diff_density_max 0.336 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.062