Chiral Brønsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of Azlactones with Aldimines.
Avila, Eloah P.; Justo, Rodrigo M. S.; Gonçalves, Vanessa P; Pereira, Adriane A.; Diniz, Renata; Amarante, Giovanni W.; The Journal of organic chemistry 80 (2014) 590–; doi:10.1021/jo5024975

data_4030317
_publ_section_title
;
 Chiral Br\/onsted Acid-Catalyzed Stereoselective Mannich-Type Reaction of
 Azlactones with Aldimines.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              590
_journal_paper_doi               10.1021/jo5024975
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H18 N2 O4 S'
_chemical_formula_sum            'C18 H18 N2 O4 S'
_chemical_formula_weight         358.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4842(5)
_cell_length_b                   13.6912(7)
_cell_length_c                   14.0603(6)
_cell_measurement_reflns_used    13950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.2859
_cell_measurement_theta_min      1.8660
_cell_volume                     1825.73(16)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
    Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
    Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.601
_diffrn_reflns_theta_min         2.076
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_coef       0.0071(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.0376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0955
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                3088
_reflns_number_total             4571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5024975_si_001.cif
_cod_data_source_block           3b
_cod_depositor_comments          'Adding full bibliography for 4030317.cif.'
_cod_database_code               4030317
_shelx_res_checksum              67819
_shelx_hkl_checksum              97321