Brønsted Acids as Additives for the Direct Asymmetric Aldol Reaction Catalyzed by L-Prolinethioamides. Direct Evidence for Enamine-Iminium Catalysis
Dorota Gryko; Magdalena Zimnicka; Radosław Lipiński; Journal of Organic Chemistry 72 (2007) 964–970; doi:10.1021/jo062149k

data_4022678
_publ_section_title
;
 Br\/onsted Acids as Additives for the Direct Asymmetric Aldol
 Reaction Catalyzed by L-Prolinethioamides. Direct Evidence for
 Enamine-Iminium Catalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              964
_journal_page_last               970
_journal_paper_doi               10.1021/jo062149k
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H19 N2 S, C F3 O3 S'
_chemical_formula_sum            'C14 H19 F3 N2 O3 S2'
_chemical_formula_weight         384.45
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.257(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7150(2)
_cell_length_b                   11.6127(4)
_cell_length_c                   26.4797(9)
_cell_measurement_temperature    120(2)
_cell_volume                     1749.98(10)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_molecular_graphics    Diamond
_computing_publication_material  SHELXTL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            33334
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        2
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 3970 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         8554
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                5743
_reflns_number_total             8554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062149ksi20061019_042105.cif
_cod_data_source_block           CF3SO3H_salt_of_L-prolinethioamide
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022678