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_4026209
_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_formula_moiety         '2(C18 H32 Cl N2 O S), H2 O'
_chemical_formula_sum            'C36 H66 Cl2 N4 O3 S2'
_chemical_formula_weight         737.97
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           170
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   17.6766(5)
_cell_length_b                   17.6766(5)
_cell_length_c                   12.3407(2)
_cell_measurement_reflns_used    1834
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     3339.40(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_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  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0734
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11755
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.93
_refine_diff_density_rms         0.14
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         6337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1234P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.2121
_reflns_number_gt                4762
_reflns_number_total             6337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1025767_si_002_7f.cif
_cod_data_source_block           M1050
_cod_original_cell_volume        3339.4(3)
_cod_original_sg_symbol_H-M      'P 65 '
_cod_database_code               4026209
_cod_database_fobs_code          4026209