A Facile Asymmetric Synthesis of Either Enantiomer of 2-Substituted Pyrrolidines
Leleti Rajender Reddy; Sonia G. Das; Yugang Liu; Mahavir Prashad; Journal of Organic Chemistry 75 (2010) 2236–2246; doi:10.1021/jo902710s

data_4025352
_publ_section_title
;
 A Facile Asymmetric Synthesis of Either Enantiomer of 2-Substituted
 Pyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2236
_journal_page_last               2246
_journal_paper_doi               10.1021/jo902710s
_journal_volume                  75
_journal_year                    2010
_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           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                 112.657(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3035(5)
_cell_length_b                   5.8935(4)
_cell_length_c                   12.2860(8)
_cell_measurement_reflns_used    5832
_cell_measurement_temperature    150.00(2)
_cell_measurement_theta_max      66
_cell_measurement_theta_min      7
_cell_volume                     755.30(8)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_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
;
 PATTY (DIRDIF99, Beurskins, 1999)
;
_diffrn_ambient_temperature      150.00(2)
_diffrn_measured_fraction_theta_full 0.9802
_diffrn_measured_fraction_theta_max 0.9552
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite 002'
_diffrn_radiation_type           CU-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5832
_diffrn_reflns_theta_full        46.1
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         6.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.914
_exptl_absorpt_correction_T_max  0.6426
_exptl_absorpt_correction_T_min  0.3059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details 'Flack H. D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.023
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0307P)^2^+0.0440P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.059
_refine_ls_wR_factor_ref         0.059
_reflns_Friedel_coverage         1.0000
_reflns_number_gt                2296
_reflns_number_total             2343
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            jo902710s_si_001.cif
_cod_data_source_block           REDDY2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z 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        'C14 H20 Br1 N1 O1 S1'
_cod_database_code               4025352