Highly diastereoselective and enantioselective synthesis of enantiopure C2-Symmetrical vicinal diamines by reductive homocoupling of chiral N-tert-butanesulfinyl imines.
Zhong, Yu-Wu; Izumi, Kenji; Xu, Ming-Hua; Lin, Guo-Qiang; Organic letters 6 (2004) 4747–4750; doi:10.1021/ol0479803

data_1506927
_publ_section_title
;
 Highly diastereoselective and enantioselective synthesis of enantiopure
 C2-Symmetrical vicinal diamines by reductive homocoupling of chiral
 N-tert-butanesulfinyl imines.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              4747
_journal_page_last               4750
_journal_paper_doi               10.1021/ol0479803
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C23 H31 Cl5 N2 O2 S2'
_chemical_formula_weight         608.87
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.170(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4482(9)
_cell_length_b                   19.473(3)
_cell_length_c                   12.0535(17)
_cell_measurement_reflns_used    1008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.954
_cell_measurement_theta_min      5.428
_cell_volume                     1479.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0840
_diffrn_reflns_av_sigmaI/netI    0.1729
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8990
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71539
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.746
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5270
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.746
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2237
_reflns_number_total             5270
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0479803si20041002_034313.cif
_cod_data_source_block           cd2404
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C23 H31  N2 O2 S2 Cl5'
_cod_database_code               1506927