Dipeptide-Based Chiral Tertiary Amine-Catalyzed Asymmetric Conjugate Addition Reactions of 5H-Thiazol/Oxazol-4-Ones.
Li, Jiangtao; Qiu, Shuai; Ye, Xinyi; Zhu, Bo; Liu, Hongjun; Jiang, Zhiyong; The Journal of organic chemistry 81 (2016) 11916–11923; doi:10.1021/acs.joc.6b02384

data_4037455
_publ_section_title
;
 Dipeptide-Based Chiral Tertiary Amine-Catalyzed Asymmetric Conjugate
 Addition Reactions of 5H-Thiazol/Oxazol-4-Ones.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11916
_journal_page_last               11923
_journal_paper_doi               10.1021/acs.joc.6b02384
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 N2 O3 S'
_chemical_formula_sum            'C20 H16 N2 O3 S'
_chemical_formula_weight         364.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.41183(15)
_cell_length_b                   10.9322(2)
_cell_length_c                   25.7034(5)
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1600
_cell_measurement_theta_min      4.3950
_cell_volume                     1801.69(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   -1.00   29.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 60

  2 omega  -16.00   42.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 116

  3 omega   30.00  128.00   0.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 196

  4 omega   88.00  113.00   0.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 50

  5 omega   32.00   71.00   0.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 78

  6 omega   10.00   65.00   0.5000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -56.0000  -17.0000 110

  7 omega  107.00  160.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -180.0000 106

  8 omega   62.00   90.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 56

  9 omega   90.00  152.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 124

 10 omega   47.00   93.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 92

 11 omega   68.00  151.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 166
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0956406000
_diffrn_orient_matrix_UB_12      -0.0528891000
_diffrn_orient_matrix_UB_13      -0.0501793000
_diffrn_orient_matrix_UB_21      0.1305088000
_diffrn_orient_matrix_UB_22      -0.0899660000
_diffrn_orient_matrix_UB_23      0.0327070000
_diffrn_orient_matrix_UB_31      -0.1774416000
_diffrn_orient_matrix_UB_32      -0.0946868000
_diffrn_orient_matrix_UB_33      -0.0029853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4244
_diffrn_reflns_theta_full        67.01
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       0.0008(2)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0458P)^2^+0.1194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                2499
_reflns_number_total             2806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02384_si_002.cif
_cod_data_source_block           201412285a
_cod_original_cell_volume        1801.69(7)
_cod_database_code               4037455
_chemical_oxdiff_formula         C20H20N4O4S1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'