Intramolecular Sulfur Transfer in N-Enoyl Oxazolidine-2-thiones Promoted by Brønsted Acids. Practical Asymmetric Synthesis of β-Mercapto Carboxylic Acids and Mechanistic Insights
Claudio Palomo; Mikel Oiarbide; Rosa López; Pedro B. González; Enrique Gómez-Bengoa; José M. Saá; Anthony Linden; Journal of the American Chemical Society 128 (2006) 15236–15247; doi:10.1021/ja0654027

data_4111145
_publ_section_title
;
 Intramolecular Sulfur Transfer in N-Enoyl Oxazolidine-2-thiones Promoted
 by Br\/onsted Acids. Practical Asymmetric Synthesis of \b-Mercapto
 Carboxylic Acids and Mechanistic Insights
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15236
_journal_page_last               15247
_journal_paper_doi               10.1021/ja0654027
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N O3 S'
_chemical_formula_sum            'C15 H19 N O3 S'
_chemical_formula_weight         293.38
_chemical_melting_point          317
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             05-05-11
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9475(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8297(3)
_cell_length_b                   5.8719(1)
_cell_length_c                   18.6094(3)
_cell_measurement_reflns_used    23130
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     1509.21(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR590 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39791
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       0.0161(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6849
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.3173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                5881
_reflns_number_total             6849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0654027si20060727_072818.cif
_cod_data_source_block           4e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4111145