Asymmetric synthesis of homoallylic amines bearing adjacent stereogenic centers by addition of substituted allylic zinc reagents to N-tert-butanesulfinylimines.
Reddy, Leleti Rajender; Hu, Bin; Prashad, Mahavir; Prasad, Kapa; Organic letters 10 (2008) 3109–3112; doi:10.1021/ol800998u

data_1504743
_publ_section_title
;
 Asymmetric synthesis of homoallylic amines bearing adjacent stereogenic
 centers by addition of substituted allylic zinc reagents to
 N-tert-butanesulfinylimines.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3109
_journal_page_last               3112
_journal_paper_doi               10.1021/ol800998u
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 Br1 N1 O1 S1'
_chemical_formula_sum            'C20 H24 Br N O S'
_chemical_formula_weight         406.39
_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_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 91.402(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5271(5)
_cell_length_b                   21.4263(17)
_cell_length_c                   9.7891(6)
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     1997.7(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_molecular_graphics
;
    ORTEP (Johnson, 1976)
    PLATON (Spek, 1997)
;
_computing_publication_material  'SHELX97(Sheldrick, 1997) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution
;
 Direct methods (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9821
_diffrn_measured_fraction_theta_max 0.9563
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9830
_diffrn_reflns_theta_full        24.4
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_T_max  0.7850
_exptl_absorpt_correction_T_min  0.7475
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_platon_squeeze_details
'                                                                       '
_refine_diff_density_max         1.66
_refine_diff_density_min         -0.60
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.088(18)
_refine_ls_extinction_coef       0.15E-01
_refine_ls_extinction_method     'SHELXL97 (Sheldrick 1997)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         5517
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.076
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.1351P)^2^+5.5863P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.210
_refine_ls_wR_factor_ref         0.216
_reflns_Friedel_coverage         0.7877
_reflns_number_gt                4747
_reflns_number_total             5517
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            ol800998u-file003.cif
_cod_data_source_block           SUL120
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
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_formula_sum        'C20 H24 Br1 N1 O1 S1'
_cod_database_code               1504743
_exptl_absorpt_correction_details 'SCALEPACK (Otwinowski & Minor, 1997)'