Nitro-Mannich/lactamization cascades for the direct stereoselective synthesis of pyrrolidin-2-ones.
Pelletier, Sophie M.-C.; Ray, Peter C.; Dixon, Darren J.; Organic letters 11 (2009) 4512–4515; doi:10.1021/ol901640v

data_1504133
_publ_section_title
;
 Nitro-Mannich/lactamization cascades for the direct stereoselective
 synthesis of pyrrolidin-2-ones.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4512
_journal_page_last               4515
_journal_paper_doi               10.1021/ol901640v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H16 N2 O3 S'
_chemical_formula_sum            'C12 H16 N2 O3 S'
_chemical_formula_weight         268.34
_chemical_melting_point          ?
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-07-14
_audit_creation_method           CRYSTALS_ver_12.87
_cell_angle_alpha                90
_cell_angle_beta                 105.9822(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2673(1)
_cell_length_b                   25.0168(5)
_cell_length_c                   8.7697(2)
_cell_measurement_reflns_used    2654
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1321.84(5)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10340
_diffrn_reflns_theta_full        25.829
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         5.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9578
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.0005795
_refine_ls_shift/su_mean         0.8450750
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 17.6 23.3 10.8 2.80 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0884
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0884
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              32
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2164
_reflns_number_total             2982
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.36
_oxford_diffrn_Wilson_scale      1.78
_oxford_refine_ls_r_factor_ref   0.0652
_oxford_refine_ls_scale          0.817(2)
_oxford_reflns_number_all        2982
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 003djd09
_cod_data_source_file            ol901640v_si_001.cif
_cod_data_source_block           7t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Monoclinic' changed to 'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               1504133