Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of Atropisomeric N-tert-Butanesulfinylketimines
Marina Martjuga; Sergey Belyakov; Edvards Liepinsh; Edgars Suna; Journal of Organic Chemistry 76 (2011) 2635–2647; doi:10.1021/jo1025767

data_4026207
_publ_section_title
;
 Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of
 Atropisomeric N-tert-Butanesulfinylketimines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2635
_journal_page_last               2647
_journal_paper_doi               10.1021/jo1025767
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H27 Cl N2 O S'
_chemical_formula_sum            'C16 H27 Cl N2 O S'
_chemical_formula_weight         330.91
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7074(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2036(4)
_cell_length_b                   8.6192(3)
_cell_length_c                   10.5131(6)
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      0.9
_cell_volume                     905.36(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0067
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3697
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       'Prism '
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.195
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0850P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                3258
_reflns_number_total             3655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1025767_si_002_5e.cif
_cod_data_source_block           1031
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4026207
_cod_database_fobs_code          4026207