Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent
Marina Martjuga; Dmitry Shabashov; Sergey Belyakov; Edvards Liepinsh; Edgars Suna; Journal of Organic Chemistry 75 (2010) 2357–2368; doi:10.1021/jo100173f

data_4025343
_publ_section_title
;
 Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of
 Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of
 the ortho-Substituent
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2357
_journal_page_last               2368
_journal_paper_doi               10.1021/jo100173f
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C17 H21 Cl N2 O S '
_chemical_formula_sum            'C17 H21 Cl N2 O S'
_chemical_formula_weight         336.885
_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           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5514(3)
_cell_length_b                   11.4813(3)
_cell_length_c                   16.0868(6)
_cell_measurement_reflns_used    19765
_cell_measurement_temperature    223
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      0.9
_cell_volume                     1764.12(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.03961
_diffrn_orient_matrix_UB_12      -0.06764
_diffrn_orient_matrix_UB_13      -0.06941
_diffrn_orient_matrix_UB_21      0.01214
_diffrn_orient_matrix_UB_22      0.06513
_diffrn_orient_matrix_UB_23      -0.05654
_diffrn_orient_matrix_UB_31      0.05689
_diffrn_orient_matrix_UB_32      0.00952
_diffrn_orient_matrix_UB_33      0.02318
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5169
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.34
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Prism (0.17x0.26x0.31 mm)'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.77
_refine_diff_density_min         -1.01
_refine_diff_density_rms         0.25
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   2.035
_refine_ls_goodness_of_fit_gt    1.785
_refine_ls_goodness_of_fit_ref   1.782
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.126
_refine_ls_R_factor_gt           0.058
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.369
_refine_ls_wR_factor_gt          0.137
_refine_ls_wR_factor_ref         0.137
_reflns_d_resolution_high        0.60
_reflns_d_resolution_low         2.16
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1741
_reflns_number_total             2888
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            jo100173f_si_014.cif
_cod_data_source_block           VJ199
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value
22 times.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C17 H21 Cl N2 O S '
_cod_database_code               4025343
_cod_database_fobs_code          4025343