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_4037454
_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 H15 Br N2 O4'
_chemical_formula_sum            'C20 H15 Br N2 O4'
_chemical_formula_weight         427.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.003(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2873(5)
_cell_length_b                   11.0497(5)
_cell_length_c                   13.8394(8)
_cell_measurement_reflns_used    1616
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8890
_cell_measurement_theta_min      4.6360
_cell_volume                     960.14(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41k (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -85.00   4.00   1.00   10.00    --  -15.33 -37.00 120.00   89
  2  \w    -25.00  57.00   1.00   10.00    --   18.22 -99.00  30.00   82
  3  \w     21.00  86.00   1.00   10.00    --   18.22  37.00 120.00   65
  4  \w     41.00  79.00   1.00   10.00    --   18.22 178.00 -30.00   38
  5  \w      1.00  86.00   1.00   10.00    --   18.22  57.00  60.00   85
  6  \w    -13.00  34.00   1.00   10.00    --   18.22 -57.00 -90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0641366000
_diffrn_orient_matrix_UB_12      0.0115854000
_diffrn_orient_matrix_UB_13      0.0396176000
_diffrn_orient_matrix_UB_21      0.0928322000
_diffrn_orient_matrix_UB_22      0.0114738000
_diffrn_orient_matrix_UB_23      0.0299531000
_diffrn_orient_matrix_UB_31      -0.0051469000
_diffrn_orient_matrix_UB_32      0.0621008000
_diffrn_orient_matrix_UB_33      -0.0129300000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 880 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0499P)^2^+0.1034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2676
_reflns_number_total             3917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02384_si_003.cif
_cod_data_source_block           qsmpbr
_cod_database_code               4037454
_chemical_oxdiff_formula         C1H1N1O1Br1
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              10114
_shelx_hkl_checksum              56137
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.755