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_4026200
_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         'C12 H18 N2 O S'
_chemical_formula_sum            'C12 H18 N2 O S'
_chemical_formula_weight         238.34
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5330(3)
_cell_length_b                   10.9995(4)
_cell_length_c                   11.9696(5)
_cell_measurement_reflns_used    1893
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     1255.11(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3623
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       'Prism '
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.183
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0571
_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^)+(0.1208P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                2794
_reflns_number_total             3603
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1025767_si_002_4a.cif
_cod_data_source_block           4a
_cod_database_code               4026200
_cod_database_fobs_code          4026200