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_1504742
_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         'C17 H24 Br1 N1 O1 S1'
_chemical_formula_sum            'C17 H24 Br N O S'
_chemical_formula_weight         370.36
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_type_scat_source
'International Tables for Crystallography (Vol C)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.4237(14)
_cell_length_b                   20.3095(10)
_cell_length_c                   8.6895(3)
_cell_measurement_reflns_used    29628
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     3604.4(3)
_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, 2008) and local programs'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution
;
 Direct methods (Charge Flipping, Oszlanyi and Suto, 2004 in PLATON, Spek, 1997)
;
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.9222
_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  0.099
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            29628
_diffrn_reflns_theta_full        25.1
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  0.8373
_exptl_absorpt_correction_T_min  0.3208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.93
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         8124
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.079
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.6970P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.087
_refine_ls_wR_factor_ref         0.099
_reflns_Friedel_coverage         0.8725
_reflns_number_gt                5902
_reflns_number_total             8124
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            ol800998u-file002.cif
_cod_data_source_block           S111
_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 

The following automatic conversions were performed:

data name '_exptl_absorpt__process_details' was replaced with
'_exptl_absorpt_process_details' as specified in the replacement file
'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_formula_sum        'C17 H24 Br1 N1 O1 S1'
_cod_database_code               1504742