Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst
Zhu, Bo; Qiu, Shuai; Li, Jiangtao; Coote, Michelle L.; Lee, Richmond; Jiang, Zhiyong; Chem. Sci. 7 (2016) 6060–; doi:10.1039/C6SC02039A

data_1543432
_publ_section_title
;
 Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral
 dipeptide-based Br\/onsted base catalyst
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              6060
_journal_paper_doi               10.1039/C6SC02039A
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 N3 O3 S'
_chemical_formula_sum            'C21 H17 N3 O3 S'
_chemical_formula_weight         391.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-08-19 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.738(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.9522(4)
_cell_length_b                   12.8653(2)
_cell_length_c                   33.3636(10)
_cell_measurement_reflns_used    4597
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1190
_cell_measurement_theta_min      4.1580
_cell_volume                     8078.7(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega    9.00   42.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 66

  2 omega   16.00   65.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 98

  3 omega  -60.00  -32.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 56

  4 omega   55.00  122.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   60.0000 134

  5 omega   19.00   86.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000    0.0000 134

  6 omega   88.00  117.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 58

  7 omega   61.00  115.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 108

  8 omega   -4.00   92.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  150.0000 192

  9 omega   43.00   71.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 56

 10 omega   57.00  105.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 96

 11 omega   55.00   90.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 70

 12 omega   90.00  176.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 172

 13 omega   40.00   90.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 100

 14 omega   43.00   76.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 66

 15 omega   41.00   98.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 114

 16 omega  118.00  178.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 120

 17 omega   42.00   75.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 66

 18 omega   62.00  156.00   0.5000   27.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   60.0000 188

 19 omega  -77.00  -52.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0635675000
_diffrn_orient_matrix_UB_12      -0.0071658000
_diffrn_orient_matrix_UB_13      0.0247048000
_diffrn_orient_matrix_UB_21      0.0500769000
_diffrn_orient_matrix_UB_22      -0.0365663000
_diffrn_orient_matrix_UB_23      0.0370395000
_diffrn_orient_matrix_UB_31      0.0121604000
_diffrn_orient_matrix_UB_32      0.1137795000
_diffrn_orient_matrix_UB_33      0.0134794000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            16457
_diffrn_reflns_theta_full        72.45
_diffrn_reflns_theta_max         72.45
_diffrn_reflns_theta_min         4.00
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79262
_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_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1013
_refine_ls_number_reflns         10564
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0736P)^2^+2.0683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                8387
_reflns_number_total             10564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc02039a2.cif
_cod_data_source_block           qs10050b
_cod_depositor_comments
'Adding full bibliography for 1543432--1543434.cif.'
_cod_database_code               1543432
_chemical_oxdiff_formula         C20H20N4O4S1
_reflns_odcompleteness_completeness 99.68
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C11B(H11B), C11C(H11C), C12B(H12B), C12C(H12C),
 C11A(H11A), C12A(H12A)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), N2B(H2B), N2C(H2C), C1B(H1B), C1C(H1C),
 C2B(H2BA), C2C(H2CA), C3B(H3B), C3C(H3C), C4B(H4B), C4C(H4C), C7B(H7B),
 C7C(H7C), C8B(H8B), C8C(H8C), C17B(H17B), C17C(H17C), C18B(H18B), C18C(H18C),
 C19B(H19B), C19C(H19C), C20B(H20B), C20C(H20C), C21B(H21B), C21C(H21C),
 N2A(H2AA), C1A(H1A), C2A(H2AB), C3A(H3A), C4A(H4A), C7A(H7A), C8A(H8A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15B(H15D,H15E,H15F), C15C(H15G,H15H,H15I), C15A(H15J,
 H15K,H15L)
;
_olex2_submission_special_instructions 'No special instructions were received'