Silyloxide-promoted diastereoselective addition of aryl and heterocyclic trimethylsilanes to N-tert-butanesulfinylimines.
Das, Manas; O'Shea, Donal F; Organic letters 17 (2015) 1962–1965; doi:10.1021/acs.orglett.5b00697

data_1554934
_publ_section_title
;
 Silyloxide-promoted diastereoselective addition of aryl and heterocyclic
 trimethylsilanes to N-tert-butanesulfinylimines.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1962
_journal_page_last               1965
_journal_paper_doi               10.1021/acs.orglett.5b00697
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H23 Fe N O2 S'
_chemical_formula_sum            'C19 H23 Fe N O2 S'
_chemical_formula_weight         385.29
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.4227(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.84461(4)
_cell_length_b                   11.31320(6)
_cell_length_c                   13.82900(8)
_cell_measurement_reflns_used    15332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.6300
_cell_measurement_theta_min      5.0340
_cell_volume                     910.298(10)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19017
_diffrn_reflns_theta_full        76.82
_diffrn_reflns_theta_max         76.82
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    7.794
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.251
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET) 
(compiled Dec 19 2012,11:08:27) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.3390
_exptl_crystal_size_mid          0.1119
_exptl_crystal_size_min          0.0473
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.0157(19)
_refine_ls_extinction_coef       0.0023(2)
_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   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0199
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+0.1794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0499
_reflns_number_gt                3772
_reflns_number_total             3808
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol5b00697_si_002.cif
_cod_data_source_block           osh118
_cod_original_cell_volume        910.298(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554934