Highly Enantioselective Organocatalytic α-Sulfenylation of Azlactones.
Qiao, Baokun; Liu, Xinfei; Duan, Shaobo; Yan, Lin; Jiang, Zhiyong; Organic letters 16 (2014) 672–675; doi:10.1021/ol403303k

data_1513506
_publ_section_title
;
 Highly Enantioselective Organocatalytic \a-Sulfenylation of Azlactones.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              672
_journal_page_last               675
_journal_paper_doi               10.1021/ol403303k
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 N O2 S'
_chemical_formula_sum            'C23 H19 N O2 S'
_chemical_formula_weight         373.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.235(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4040(2)
_cell_length_b                   10.9966(2)
_cell_length_c                   11.7955(4)
_cell_measurement_reflns_used    4005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.1660
_cell_measurement_theta_min      3.9860
_cell_volume                     1022.81(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1610562000
_diffrn_orient_matrix_UB_12      -0.0788046000
_diffrn_orient_matrix_UB_13      0.0485398000
_diffrn_orient_matrix_UB_21      -0.0859688000
_diffrn_orient_matrix_UB_22      -0.0785171000
_diffrn_orient_matrix_UB_23      0.0703781000
_diffrn_orient_matrix_UB_31      -0.0696790000
_diffrn_orient_matrix_UB_32      -0.0851268000
_diffrn_orient_matrix_UB_33      -0.1098682000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8052
_diffrn_reflns_theta_full        72.42
_diffrn_reflns_theta_max         72.42
_diffrn_reflns_theta_min         3.99
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             392
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0569P)^2^+0.0280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                3690
_reflns_number_total             3936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403303k_si_002.cif
_cod_data_source_block           201310184
_cod_original_cell_volume        1022.82(5)
_cod_database_code               1513506
_chemical_oxdiff_formula         C18H12N1O2S1
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;