An Organocatalyst Bearing Stereogenic Carbon and Sulfur Centers as an Efficient Promoter for Enantioselective Hydrosilylation of 1,4-Benzooxazines
Xiang-Wei Liu; Chao Wang; Yan Yan; Yong-Qiang Wang; Jian Sun; Journal of Organic Chemistry 78 (2013) 6276–6280; doi:10.1021/jo400187e

data_4028324
_publ_contact_author_name
;
;
_publ_section_title
;
 An Organocatalyst Bearing Stereogenic Carbon and Sulfur Centers as an
 Efficient Promoter for Enantioselective Hydrosilylation of
 1,4-Benzooxazines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6276
_journal_page_last               6280
_journal_paper_doi               10.1021/jo400187e
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 N2 O2 S'
_chemical_formula_sum            'C20 H26 N2 O2 S'
_chemical_formula_weight         358.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0113(5)
_cell_length_b                   11.3161(6)
_cell_length_c                   17.9297(9)
_cell_measurement_reflns_used    1465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1357
_cell_measurement_theta_min      2.8929
_cell_volume                     2031.24(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -82.00  -14.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8924  -57.0000   30.0000 68

  2 omega  -23.00    3.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0174  -99.0000  -60.0000 26

  3 omega    0.00   46.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0174  -77.0000 -120.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0116857000
_diffrn_orient_matrix_UB_12      -0.0242914000
_diffrn_orient_matrix_UB_13      0.0359030000
_diffrn_orient_matrix_UB_21      0.0069886000
_diffrn_orient_matrix_UB_22      0.0577696000
_diffrn_orient_matrix_UB_23      0.0148402000
_diffrn_orient_matrix_UB_31      -0.0694916000
_diffrn_orient_matrix_UB_32      0.0016971000
_diffrn_orient_matrix_UB_33      0.0075379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5523
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enhance (Mo) x-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0556P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2324
_reflns_number_total             3815
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400187e_si_001.cif
_cod_data_source_block           120710_s2_lxw
_cod_original_cell_volume        2031.23(18)
_cod_database_code               4028324
_chemical_oxdiff_formula         C22H17N1O2S1
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32