Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a Cinchona-derived phase-transfer reagent.
Gelat, Fabien; Jayashankaran, Jayadevan; Lohier, Jean-François; Gaumont, Annie-Claude; Perrio, Stéphane; Organic letters 13 (2011) 3170–3173; doi:10.1021/ol2010962

data_1502238
_publ_section_title
;
 Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid
 anions mediated by a Cinchona-derived phase-transfer reagent.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3170
_journal_page_last               3173
_journal_paper_doi               10.1021/ol2010962
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H13 Cl O3 S2'
_chemical_formula_sum            'C14 H13 Cl O3 S2'
_chemical_formula_weight         328.81
_chemical_name_systematic
; 
 2-[(4-Chlorophenyl)sulfinyl]ethyl Phenyl Sulfone 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.1780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4437(2)
_cell_length_b                   5.73830(10)
_cell_length_c                   19.0506(3)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      3.05
_cell_volume                     1462.14(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30343
_diffrn_reflns_theta_full        29.11
_diffrn_reflns_theta_max         29.11
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.3688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3312
_reflns_number_total             3918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2010962_si_001.cif
_cod_data_source_block           1i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               1502238