Asymmetric synthesis of 2-substituted pyrrolidines by addition of Grignard reagents to gamma-chlorinated N-tert-butanesulfinyl imine.
Reddy, Leleti Rajender; Prashad, Mahavir; Chemical communications (Cambridge, England) 46 (2009) 222–224; doi:10.1039/b917435d

data_7105144
_publ_section_title
;
 Asymmetric synthesis of 2-substituted pyrrolidines by addition of
 Grignard reagents to gamma-chlorinated N-tert-butanesulfinyl imine.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              222
_journal_page_last               224
_journal_paper_doi               10.1039/b917435d
_journal_volume                  46
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 Br1 N1 O1 S1'
_chemical_formula_sum            'C14 H20 Br N O S'
_chemical_formula_weight         330.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.1888(4)
_cell_length_b                   10.0920(6)
_cell_length_c                   24.6826(17)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1541.61(17)
_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 (SIR2004, Burla et al., 2005)
;
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.9855
_diffrn_measured_fraction_theta_max 0.9415
_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  0.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            3679
_diffrn_reflns_theta_full        23.0
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.954
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.7432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.066(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0201P)^2^+0.1612P] where P=(Fo^2^+2Fc^2^)/3 '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.064
_refine_ls_wR_factor_ref         0.077
_reflns_Friedel_coverage         0.7767
_reflns_number_gt                2390
_reflns_number_total             3654
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            b917435d.txt
_cod_data_source_block           REDDY1
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C14 H20 Br1 N1 O1 S1'
_cod_database_code               7105144