Switchable C2/C3 positional selectivity of thioisatins in a three-component domino reaction: combined computational and experimental studies
Liu, Baolin; Deng, Qingsong; Zhang, Lei; Meng, Xiangtai; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01764D

data_7158968
_publ_section_title
;
 Switchable C2/C3 positional selectivity of thioisatins in a
 three-component domino reaction: combined computational and experimental
 studies
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01764D
_journal_year                    2022
_chemical_formula_moiety         'C20 H18 N2 O S'
_chemical_formula_sum            'C20 H18 N2 O S'
_chemical_formula_weight         334.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.301(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5789(2)
_cell_length_b                   7.19470(10)
_cell_length_c                   18.2456(3)
_cell_measurement_reflns_used    7590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0770
_cell_measurement_theta_min      3.4000
_cell_volume                     1710.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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    -44.00  18.00   0.50    0.56    --   42.30 -82.00-120.00  124
  2  \w     26.00  66.00   0.50    0.56    --   42.30 -77.00  60.00   80
  3  \w     45.00  70.00   0.50    0.56    --   42.30 -82.00 150.00   50
  4  \w     23.00  55.00   0.50    0.56    --   42.30  77.00 150.00   64
  5  \w     40.00  70.00   0.50    0.56    --   42.30 -82.00  30.00   60
  6  \w     19.00  74.00   0.50    0.56    --   42.30  82.00-150.00  110
  7  \w     42.00  69.00   0.50    0.56    --   42.30 -82.00 120.00   54
  8  \w     -6.00  67.00   0.50    0.56    --   42.30 -82.00   0.00  146
  9  \w    -47.00  15.00   0.50    0.56    --   42.30 -82.00 150.00  124
 10  \w     59.00  96.00   0.50    0.56    --   42.30  77.00 150.00   74
 11  \w     18.00  97.00   0.50    0.56    --   42.30  54.00 -30.00  158
 12  \w     24.00  68.00   0.50    0.56    --   42.30 -82.00-120.00   88
 13  \w    -12.00  58.00   0.50    0.56    --   42.30 -82.00 -60.00  140
 14  \w     87.00 130.00   0.50    0.56    --   42.30  82.00-150.00   86
 15  \w     46.00  71.00   0.50    0.56    --   42.30 -54.00 -90.00   50
 16  \w    -31.00  -3.00   0.50    0.56    --   42.30 -54.00 -90.00   56
 17  \w     -4.00  21.00   0.50    0.56    --   42.30 -82.00 120.00   50
 18  \w    -47.00  -1.00   0.50    0.56    --   42.30 -77.00  60.00   92
 19  \w     64.00 100.00   0.50    0.80    --   93.70 -82.00  30.00   72
 20  \w      6.00 109.00   0.50    0.80    --   93.70 -82.00-150.00  206
 21  \w      5.00  35.00   0.50    0.80    --   93.70 -50.00  90.00   60
 22  \w     91.00 137.00   0.50    0.80    --   93.70  82.00   0.00   92
 23  \w    122.00 170.00   0.50    0.80    --   93.70  33.00 -90.00   96
 24  \w     74.00 105.00   0.50    0.80    --   93.70 -82.00 120.00   62
 25  \w      6.00 182.00   0.50    0.80    --   93.70  17.00  90.00  352
 26  \w     62.00  88.00   0.50    0.80    --   93.70 -82.00 150.00   52
 27  \w     55.00  94.00   0.50    0.80    --   93.70 -82.00 -30.00   78
 28  \w      5.00  41.00   0.50    0.80    --   93.70 -82.00-180.00   72
 29  \w     61.00  90.00   0.50    0.80    --   93.70 -82.00-180.00   58
 30  \w     25.00  71.00   0.50    0.80    --   93.70 -82.00-120.00   92
 31  \w      4.00 120.00   0.50    0.80    --   93.70 -82.00 -60.00  232
 32  \w     83.00 109.00   0.50    0.80    --   93.70 -82.00   0.00   52
 33  \w      4.00  82.00   0.50    0.80    --   93.70 -82.00 -90.00  156
 34  \w      5.00  31.00   0.50    0.80    --   93.70 -42.00-150.00   52
 35  \w     27.00  55.00   0.50    0.80    --   93.70 -77.00  60.00   56
 36  \w    158.00 183.00   0.50    0.80    --   93.70  68.00 120.00   50
 37  \w    103.00 129.00   0.50    0.80    --   93.70  68.00 120.00   52
 38  \w     70.00  97.00   0.50    0.80    --   93.70  68.00 120.00   54
 39  \w     41.00 103.00   0.50    0.80    --   93.70 -50.00  90.00  124
 40  \w     65.00 152.00   0.50    0.80    --   93.70  33.00-180.00  174
 41  \w     10.00 123.00   0.50    0.80    --   93.70 -50.00 -60.00  226
 42  \w     15.00  95.00   0.50    0.80    --   93.70 -82.00  87.55  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0875643000
_diffrn_orient_matrix_UB_12      0.0459982000
_diffrn_orient_matrix_UB_13      -0.0719374000
_diffrn_orient_matrix_UB_21      0.0716606000
_diffrn_orient_matrix_UB_22      -0.0409019000
_diffrn_orient_matrix_UB_23      -0.0501552000
_diffrn_orient_matrix_UB_31      -0.0340349000
_diffrn_orient_matrix_UB_32      -0.2053204000
_diffrn_orient_matrix_UB_33      -0.0061473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14768
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.307
_diffrn_reflns_theta_min         3.391
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0512P)^2^+0.3628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2791
_reflns_number_total             3121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01764d2.cif
_cod_data_source_block           exp_1162_auto
_cod_database_code               7158968
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.97
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N21(H21), C19(H19), C16(H16), C4(H4), C17(H17), C6(H6), C7(H7), C18(H18)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              20459
_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 1.499
_oxdiff_exptl_absorpt_empirical_full_min 0.655