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_4025335
_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         'C22 H23 Cl N2 O S '
_chemical_formula_sum            'C22 H23 Cl N2 O S'
_chemical_formula_weight         398.94
_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
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 103.897(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1510(4)
_cell_length_b                   9.6705(4)
_cell_length_c                   18.2329(8)
_cell_measurement_reflns_used    35077
_cell_measurement_temperature    193
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      0.998
_cell_volume                     2079.77(14)
_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)'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02644
_diffrn_orient_matrix_UB_12      0.07384
_diffrn_orient_matrix_UB_13      -0.03218
_diffrn_orient_matrix_UB_21      -0.08934
_diffrn_orient_matrix_UB_22      0.04408
_diffrn_orient_matrix_UB_23      0.02772
_diffrn_orient_matrix_UB_31      0.02591
_diffrn_orient_matrix_UB_32      0.02522
_diffrn_orient_matrix_UB_33      0.04341
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7901
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.30
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Prism (0.11x0.17x0.28 mm)'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.78
_refine_diff_density_rms         0.16
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.725
_refine_ls_goodness_of_fit_gt    1.797
_refine_ls_goodness_of_fit_ref   1.772
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     496
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.100
_refine_ls_R_factor_gt           0.068
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_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         0.236
_refine_ls_wR_factor_gt          0.205
_refine_ls_wR_factor_ref         0.205
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         2.43
_reflns_limit_h_max              15
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -23
_reflns_number_gt                3506
_reflns_number_total             5036
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            jo100173f_si_006.cif
_cod_data_source_block           M870
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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 
;
_cod_original_sg_symbol_H-M      'P 21 '
_cod_original_formula_sum        'C22 H23 Cl N2 O S '
_cod_database_code               4025335
_cod_database_fobs_code          4025335