Catalytic asymmetric aromatizing inverse electron-demand [4+2] cycloaddition of 1-thioaurones and 1-azaaurones
Yuan, Shu-Pei; Dou, Pei-Hao; Jia, Yun-Qing; Zhao, Jian-Qiang; You, Yong; Wang, Zhen-Hua; Zhou, Ming-Qiang; Yuan, Weicheng; Chemical Communications  (2021) –; doi:10.1039/D1CC06357J

data_7129367
_publ_section_title
;
 Catalytic asymmetric aromatizing inverse electron-demand [4+2]
 cycloaddition of 1-thioaurones and 1-azaaurones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06357J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H18 O3 S'
_chemical_formula_sum            'C25 H18 O3 S'
_chemical_formula_weight         398.45
_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
_audit_creation_date             2021-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-10 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1738(2)
_cell_length_b                   11.5881(2)
_cell_length_c                   18.4905(4)
_cell_measurement_reflns_used    6419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8220
_cell_measurement_theta_min      4.4930
_cell_volume                     1965.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -102.00 -47.00   1.00    1.50    --  -33.50 178.00-120.00   55
  2  \w     74.00 105.00   1.00    1.50    --   36.47  57.00 150.00   31
  3  \w     57.00 108.00   1.00    1.50    --   36.47 178.00 -90.00   51
  4  \w     58.00  85.00   1.00    1.50    --   36.47 178.00-120.00   27
  5  \w      8.00  38.00   1.00    1.50    --   36.47 -37.00 -60.00   30
  6  \w     44.00  70.00   1.00    1.50    --   36.47  57.00-150.00   26
  7  \w     76.00 102.00   1.00    1.50    --   36.47  77.00 -90.00   26
  8  \w     51.00  77.00   1.00    1.50    --   36.47  77.00-150.00   26
  9  \w     28.00  54.00   1.00    1.50    --   36.47  77.00 -90.00   26
 10  \w     40.00  82.00   1.00    1.50    --   36.47  37.00-120.00   42
 11  \w    -32.00  14.00   1.00    1.50    --   36.47 -77.00-150.00   46
 12  \w    -34.00  -9.00   1.00    1.50    --   36.47 -37.00 -60.00   25
 13  \w     23.00  56.00   1.00    1.50    --   36.47  57.00-180.00   33
 14  \w     20.00  67.00   1.00    1.50    --   36.47  77.00 -60.00   47
 15  \w    -28.00  63.00   1.00    1.50    --   36.47 -77.00 -60.00   91
 16  \w     27.00  61.00   1.00    1.50    --   36.47 -99.00 120.00   34
 17  \w     18.00  52.00   1.00    1.50    --   36.47  57.00 150.00   34
 18  \w     13.00  38.00   1.00    1.50    --   36.47  77.00-150.00   25
 19  \w     19.00 105.00   1.00    1.50    --   36.47  51.00  82.00   86
 20  \w     79.00 105.00   1.00    7.50    --  108.00  77.00-180.00   26
 21  \w     88.00 119.00   1.00    7.50    --  108.00  61.00 150.00   31
 22  \w     82.00 109.00   1.00    7.50    --  108.00  30.00 -90.00   27
 23  \w     85.00 122.00   1.00    7.50    --  108.00  30.00-150.00   37
 24  \w     82.00 107.00   1.00    7.50    --  108.00  30.00-120.00   25
 25  \w     83.00 113.00   1.00    7.50    --  108.00  30.00 150.00   30
 26  \w    115.00 156.00   1.00    7.50    --  108.00  30.00   0.00   41
 27  \w     67.00 102.00   1.00    7.50    --  108.00 -45.00  60.00   35
 28  \w    120.00 164.00   1.00    7.50    --  108.00  77.00 120.00   44
 29  \w     38.00 106.00   1.00    7.50    --  108.00 -94.00-150.00   68
 30  \w     88.00 114.00   1.00    7.50    --  108.00  61.00-180.00   26
 31  \w     79.00 105.00   1.00    7.50    --  108.00  77.00 120.00   26
 32  \w     42.00 128.00   1.00    7.50    --  108.00 -45.00 150.00   86
 33  \w     88.00 116.00   1.00    7.50    --  108.00  45.00-120.00   28
 34  \w    125.00 166.00   1.00    7.50    --  108.00  77.00-150.00   41
 35  \w     88.00 118.00   1.00    7.50    --  108.00  45.00-180.00   30
 36  \w     82.00 110.00   1.00    7.50    --  108.00 -94.00  60.00   28
 37  \w    129.00 155.00   1.00    7.50    --  108.00  77.00 150.00   26
 38  \w     83.00 109.00   1.00    7.50    --  108.00  77.00-150.00   26
 39  \w     83.00 178.00   1.00    7.50    --  108.00  30.00-180.00   95
 40  \w     89.00 156.00   1.00    7.50    --  108.00  61.00  30.00   67
 41  \w     79.00 105.00   1.00    7.50    --  108.00  77.00 150.00   26
 42  \w     88.00 113.00   1.00    7.50    --  108.00  61.00-150.00   25
 43  \w    121.00 178.00   1.00    7.50    --  108.00 111.00  60.00   57
 44  \w     90.00 171.00   1.00    7.50    --  108.00  61.00-120.00   81
 45  \w    113.00 174.00   1.00    7.50    --  108.00  61.00  90.00   61
 46  \w     39.00 127.00   1.00    7.50    --  108.00 -51.00 -63.00   88
;
_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      -0.1074882000
_diffrn_orient_matrix_UB_12      -0.0663122000
_diffrn_orient_matrix_UB_13      0.0486823000
_diffrn_orient_matrix_UB_21      -0.0188232000
_diffrn_orient_matrix_UB_22      -0.0919444000
_diffrn_orient_matrix_UB_23      -0.0594768000
_diffrn_orient_matrix_UB_31      0.1276160000
_diffrn_orient_matrix_UB_32      -0.0693921000
_diffrn_orient_matrix_UB_33      0.0322316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.503
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3282
_reflns_number_total             3499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06357j2.cif
_cod_data_source_block           20210358
_cod_original_cell_volume        1965.66(8)
_cod_database_code               7129367
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2CS1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.766
_reflns_odcompleteness_completeness 99.85
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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 7.834
_oxdiff_exptl_absorpt_empirical_full_min 0.722