Synthesis of Nitrogenated Heterocycles by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)haloimines
Óscar Pablo; David Guijarro; Miguel Yus; Journal of Organic Chemistry 78 (2013) 9181–9189; doi:10.1021/jo4014386

data_4028604
_publ_section_title
;
 Synthesis of Nitrogenated Heterocycles by Asymmetric Transfer
 Hydrogenation of N-(tert-Butylsulfinyl)haloimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9181
_journal_page_last               9189
_journal_paper_doi               10.1021/jo4014386
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H20 F N O S'
_chemical_formula_sum            'C14 H20 F N O S'
_chemical_formula_weight         269.37
_space_group_IT_number           4
_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                 104.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.411(15)
_cell_length_b                   6.155(9)
_cell_length_c                   12.590(19)
_cell_measurement_reflns_used    597
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.4
_cell_volume                     706.8(19)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1193
_diffrn_reflns_av_sigmaI/netI    0.1762
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5782
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.6665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.796
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.796
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0015P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                1085
_reflns_number_total             2469
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo4014386_si_002.cif
_cod_data_source_block           x
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028604