Catalytic asymmetric addition of thiols to nitrosoalkenes leading to chiral non-racemic α-sulfenyl ketones.
Hatcher, John M.; Kohler, Mark C.; Coltart, Don M.; Organic letters 13 (2011) 3810–3813; doi:10.1021/ol2012633

data_1502275
_publ_section_title
;
 Catalytic asymmetric addition of thiols to nitrosoalkenes leading to
 chiral non-racemic \a-sulfenyl ketones.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3810
_journal_page_last               3813
_journal_paper_doi               10.1021/ol2012633
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C22 H28 N2 O2 S'
_chemical_formula_sum            'C22 H28 N2 O2 S'
_chemical_formula_weight         384.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   12.1885(2)
_cell_length_b                   21.5857(4)
_cell_length_c                   23.1276(4)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.6
_cell_volume                     6084.81(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            85694
_diffrn_reflns_theta_full        33.43
_diffrn_reflns_theta_max         33.43
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.8091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'parallel pipet'
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1067
_refine_ls_number_reflns         22108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.859
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                18532
_reflns_number_total             22108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2012633_si_002.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               1502275