# Copyright The Royal Society of Chemistry, 1999 # CCDC Number :182/1113 data_global #==================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Mark Thornton-Pett School of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_phone '+44 (0)113 2336423' _publ_contact_author_fax '+44 (0)113 2336565' _publ_contact_author_email marktp@chem.leeds.ac.uk _publ_requested_journal 'J. Chem. Soc., Chem Commun.' _publ_contact_letter ; The following set of data is for the cluster-compound included paper below which we have just submitted to you. ; #======================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; "Oxidation in supercritical carbon dioxide - selective formation of sulphoxides and sulfones, and dramatic pressure dependant enhancement of diastereoselectivity for oxidation of cystein derivatives" ; loop_ _publ_author_name _publ_author_address 'R. Scott Oakes' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Anthony Clifford' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Keith D. Bartle' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Mark Thornton-Pett' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Christopher M. Rayner' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; #================================================================= data_CR5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O5 S' _chemical_formula_weight 299.34 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.87930(10) _cell_length_b 8.19550(10) _cell_length_c 22.0906(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1426.50(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24188 _cell_measurement_theta_min 2.02 _cell_measurement_theta_max 30.2 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8831 _exptl_absorpt_correction_T_max 0.9526 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method ; Detector set at 25mm from sample 'head-on' data - 360 * 1 degree phi exposures for chi=0 and 2theta = 0 'cusp' data' - 55 * 1 degree omega exposures for chi=90 at 2theta = 40 at 4 different settings of phi ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27208 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2747 _reflns_number_gt 2724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KCCD (Nonius, 1997)' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material 'local program' _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^)+(0.0430P)^2^+0.3491P] 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 0.046(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(6) _refine_ls_number_reflns 2747 _refine_ls_number_parameters 184 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.59760(4) 0.48754(4) 0.171601(15) 0.02182(12) Uani 1 1 d . . . O1 O 0.68604(14) 0.64935(13) 0.17835(5) 0.0262(2) Uani 1 1 d . . . C1 C 0.5313(2) 0.4696(2) 0.09430(7) 0.0284(3) Uani 1 1 d . . . H1A H 0.4760 0.5710 0.0816 0.043 Uiso 1 1 calc R . . H1B H 0.4512 0.3787 0.0904 0.043 Uiso 1 1 calc R . . H1C H 0.6305 0.4492 0.0686 0.043 Uiso 1 1 calc R . . N1 N 0.47757(16) 0.45705(15) 0.30793(5) 0.0211(3) Uani 1 1 d . . . H1 H 0.4409 0.3556 0.3080 0.025 Uiso 1 1 calc R . . C2 C 0.38671(18) 0.51371(18) 0.20286(6) 0.0215(3) Uani 1 1 d . . . H2A H 0.3224 0.5935 0.1782 0.026 Uiso 1 1 calc R . . H2B H 0.3251 0.4085 0.2019 0.026 Uiso 1 1 calc R . . C3 C 0.40020(19) 0.57467(17) 0.26834(6) 0.0206(3) Uani 1 1 d . . . H3 H 0.4777 0.6713 0.2675 0.025 Uiso 1 1 calc R . . C4 C 0.60637(18) 0.50082(18) 0.34520(6) 0.0219(3) Uani 1 1 d . . . O4 O 0.66894(14) 0.63595(13) 0.34912(5) 0.0284(3) Uani 1 1 d . . . O5 O 0.65932(14) 0.36981(13) 0.37737(5) 0.0239(3) Uani 1 1 d . . . C5 C 0.8058(2) 0.3977(2) 0.41620(7) 0.0292(4) Uani 1 1 d D . . H5A H 0.7774 0.4759 0.4488 0.035 Uiso 1 1 calc R . . H5B H 0.9019 0.4419 0.3925 0.035 Uiso 1 1 calc R . . C6 C 0.85045(19) 0.23399(19) 0.44233(7) 0.0235(3) Uani 1 1 d D . . C7 C 0.7941(2) 0.1893(2) 0.49976(7) 0.0309(4) Uani 1 1 d D . . H7 H 0.7314 0.2650 0.5234 0.037 Uiso 1 1 calc R . . C8 C 0.8289(2) 0.0354(2) 0.52266(8) 0.0395(4) Uani 1 1 d D . . H8 H 0.7906 0.0061 0.5620 0.047 Uiso 1 1 calc R . . C9 C 0.9197(3) -0.0758(2) 0.48812(9) 0.0403(4) Uani 1 1 d D . . H9 H 0.9426 -0.1817 0.5036 0.048 Uiso 1 1 calc R . . C10 C 0.9768(2) -0.0322(2) 0.43094(8) 0.0342(4) Uani 1 1 d D . . H10 H 1.0388 -0.1084 0.4072 0.041 Uiso 1 1 calc R . . C11 C 0.9437(2) 0.1218(2) 0.40854(7) 0.0267(3) Uani 1 1 d D . . H11 H 0.9850 0.1516 0.3697 0.032 Uiso 1 1 calc R . . C12 C 0.22995(19) 0.63579(17) 0.29222(7) 0.0216(3) Uani 1 1 d . . . O12 O 0.17862(15) 0.61377(15) 0.34304(5) 0.0301(3) Uani 1 1 d . . . O13 O 0.14844(13) 0.72068(13) 0.24952(5) 0.0243(2) Uani 1 1 d . . . C13 C -0.0071(2) 0.8003(2) 0.26789(8) 0.0296(4) Uani 1 1 d . . . H13A H -0.0717 0.7275 0.2945 0.044 Uiso 1 1 calc R . . H13B H -0.0750 0.8263 0.2320 0.044 Uiso 1 1 calc R . . H13C H 0.0201 0.9012 0.2897 0.044 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 0.02221(18) 0.01968(19) 0.02357(19) -0.00012(13) 0.00087(13) 0.00184(15) O1 0.0235(5) 0.0221(5) 0.0331(6) -0.0024(4) 0.0019(5) -0.0023(4) C1 0.0310(8) 0.0302(8) 0.0240(7) -0.0025(6) 0.0030(6) -0.0017(7) N1 0.0232(6) 0.0170(6) 0.0233(6) 0.0020(4) -0.0034(5) -0.0008(5) C2 0.0213(6) 0.0209(7) 0.0222(7) 0.0000(6) -0.0007(5) 0.0011(6) C3 0.0221(7) 0.0182(6) 0.0215(7) 0.0013(5) -0.0028(6) -0.0003(6) C4 0.0230(7) 0.0213(7) 0.0216(6) 0.0004(6) -0.0006(5) 0.0024(7) O4 0.0306(6) 0.0212(5) 0.0334(6) 0.0013(4) -0.0068(5) -0.0036(5) O5 0.0256(5) 0.0195(5) 0.0267(5) 0.0023(4) -0.0074(4) 0.0005(4) C5 0.0277(8) 0.0267(8) 0.0332(8) -0.0002(6) -0.0115(7) -0.0005(7) C6 0.0217(7) 0.0261(8) 0.0227(7) -0.0013(6) -0.0055(6) -0.0007(6) C7 0.0269(8) 0.0421(10) 0.0237(7) -0.0041(7) 0.0002(7) -0.0026(7) C8 0.0433(10) 0.0494(11) 0.0257(8) 0.0109(7) -0.0050(7) -0.0122(9) C9 0.0455(10) 0.0325(9) 0.0427(10) 0.0134(7) -0.0152(9) -0.0014(8) C10 0.0329(9) 0.0318(9) 0.0378(9) -0.0033(7) -0.0075(7) 0.0056(7) C11 0.0257(7) 0.0326(9) 0.0219(7) 0.0010(6) -0.0013(6) 0.0010(6) C12 0.0233(7) 0.0178(7) 0.0237(7) -0.0014(5) -0.0024(6) -0.0003(6) O12 0.0307(6) 0.0356(6) 0.0242(6) 0.0045(5) 0.0043(5) 0.0046(5) O13 0.0231(5) 0.0260(5) 0.0238(5) 0.0002(4) -0.0014(4) 0.0058(4) C13 0.0248(7) 0.0326(9) 0.0314(8) -0.0030(6) 0.0015(7) 0.0089(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 O1 1.5055(11) . ? S1 C1 1.7918(16) . ? S1 C2 1.8122(14) . ? N1 C4 1.3551(19) . ? N1 C3 1.4372(18) . ? C2 C3 1.5342(19) . ? C3 C12 1.526(2) . ? C4 O4 1.2153(18) . ? C4 O5 1.3535(17) . ? O5 C5 1.4559(18) . ? C5 C6 1.502(2) . ? C6 C7 1.393(2) . ? C6 C11 1.394(2) . ? C7 C8 1.387(3) . ? C8 C9 1.387(3) . ? C9 C10 1.388(3) . ? C10 C11 1.381(2) . ? C12 O12 1.2068(19) . ? C12 O13 1.3366(18) . ? O13 C13 1.4466(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 C1 107.56(7) . . ? O1 S1 C2 106.40(7) . . ? C1 S1 C2 96.05(7) . . ? C4 N1 C3 120.65(12) . . ? C3 C2 S1 109.53(10) . . ? N1 C3 C12 112.50(12) . . ? N1 C3 C2 112.63(12) . . ? C12 C3 C2 111.84(12) . . ? O4 C4 O5 124.08(13) . . ? O4 C4 N1 126.04(13) . . ? O5 C4 N1 109.87(12) . . ? C4 O5 C5 115.42(11) . . ? O5 C5 C6 105.78(12) . . ? C7 C6 C11 118.84(15) . . ? C7 C6 C5 120.66(15) . . ? C11 C6 C5 120.46(14) . . ? C8 C7 C6 120.56(16) . . ? C7 C8 C9 119.93(16) . . ? C8 C9 C10 119.94(17) . . ? C11 C10 C9 120.01(17) . . ? C10 C11 C6 120.71(15) . . ? O12 C12 O13 124.99(14) . . ? O12 C12 C3 124.55(13) . . ? O13 C12 C3 110.44(12) . . ? C12 O13 C13 116.35(12) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.171 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.052