Samarium diiodide-induced asymmetric synthesis of optically pure unsymmetrical vicinal diamines by reductive cross-coupling of nitrones with N-tert-butanesulfinyl imines.
Zhong, Yu-Wu; Xu, Ming-Hua; Lin, Guo-Qiang; Organic letters 6 (2004) 3953–3956; doi:10.1021/ol048444d

data_1507000
_publ_section_title
;
 Samarium diiodide-induced asymmetric synthesis of optically pure
 unsymmetrical vicinal diamines by reductive cross-coupling of nitrones
 with N-tert-butanesulfinyl imines.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              3953
_journal_page_last               3956
_journal_paper_doi               10.1021/ol048444d
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C22 H33 N2 O2.5 S'
_chemical_formula_weight         397.56
_chemical_name_systematic
; 
 ? 
;
_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                 92.582(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9324(8)
_cell_length_b                   18.4511(16)
_cell_length_c                   14.0752(12)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.439
_cell_measurement_theta_min      5.071
_cell_volume                     2317.4(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 0.933
_diffrn_measured_fraction_theta_max 0.933
_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  0.0639
_diffrn_reflns_av_sigmaI/netI    0.1129
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14185
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35157
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(11)
_refine_ls_extinction_coef       0.0027(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         7783
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                3556
_reflns_number_total             7783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048444dsi20040806_014639.cif
_cod_data_source_block           cd23442
_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_cell_volume        2317.4(3)
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C22 H33 N2 O2.50 S'
_cod_database_code               1507000