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_7158970
_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         'C31 H28 N2 O5 S'
_chemical_formula_sum            'C31 H28 N2 O5 S'
_chemical_formula_weight         540.61
_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             2022-10-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-30 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.633(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.3292(10)
_cell_length_b                   9.8454(6)
_cell_length_c                   18.1637(10)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.5770
_cell_measurement_theta_min      2.8680
_cell_volume                     2750.4(3)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.972
_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     60.00  87.00   0.50    0.50    --   42.30  32.00 -90.00   54
  2  \w     19.00  69.00   0.50    0.50    --   42.30 -82.00  60.00  100
  3  \w     34.00  65.00   0.50    0.50    --   42.30 -82.00-150.00   62
  4  \w     91.00 121.00   0.50    0.50    --   42.30  32.00 -90.00   60
  5  \w    -45.00  12.00   0.50    0.50    --   42.30 -65.00 -30.00  114
  6  \w     21.00  89.00   0.50    0.50    --   42.30  77.00 120.00  136
  7  \w     15.00  41.00   0.50    0.50    --   42.30 -65.00-180.00   52
  8  \w     18.00 123.00   0.50    0.50    --   42.30  65.00  60.00  210
  9  \w    -47.00  13.00   0.50    0.50    --   42.30 -82.00 120.00  120
 10  \w     11.00  69.00   0.50    0.50    --   42.30 -82.00 -90.00  116
 11  \w    -47.00  51.00   0.50    0.50    --   42.30 -82.00-120.00  196
 12  \w     95.00 132.00   0.50    0.50    --   42.30  82.00 150.00   74
 13  \w    100.00 132.00   0.50    0.50    --   42.30  77.00 120.00   64
 14  \w     17.00  43.00   0.50    0.50    --   42.30 -65.00 -30.00   52
 15  \w    -36.00 -10.00   0.50    0.50    --   42.30 -82.00 -90.00   52
 16  \w     36.00  61.00   0.50    0.50    --   42.30 -77.00 -90.00   50
 17  \w     36.00  67.00   0.50    0.50    --   42.30 -82.00 120.00   62
 18  \w    -40.00 -15.00   0.50    0.50    --   42.30 -65.00-180.00   50
 19  \w     18.00  87.00   0.50    0.50    --   42.30  82.00 150.00  138
 20  \w     -5.00  21.00   0.50    0.50    --   42.30 -82.00-150.00   52
 21  \w     42.00  69.00   0.50    0.50    --   42.30 -82.00   0.00   54
 22  \w    -34.00  10.00   0.50    0.50    --   42.30 -82.00   0.00   88
 23  \w    -46.00   3.00   0.50    0.50    --   42.30 -82.00  60.00   98
 24  \w      6.00  98.00   0.50    0.50    --   93.70 -82.00 -30.00  184
 25  \w     28.00  96.00   0.50    0.50    --   93.70 -82.00 150.00  136
 26  \w    103.00 183.00   0.50    0.50    --   93.70  68.00-120.00  160
 27  \w     69.00 162.00   0.50    0.50    --   93.70  59.00   0.00  186
 28  \w     22.00 103.00   0.50    0.50    --   93.70 -82.00-180.00  162
 29  \w     86.00 171.00   0.50    0.50    --   93.70  59.00  30.00  170
 30  \w     50.00  81.00   0.50    0.50    --   93.70 -82.00 120.00   62
 31  \w     37.00  97.00   0.50    0.50    --   93.70 -82.00   0.00  120
 32  \w     65.00  91.00   0.50    0.50    --   93.70 -82.00 -60.00   52
 33  \w     10.00 104.00   0.50    0.50    --   93.70 -82.00-120.00  188
 34  \w      5.00  30.00   0.50    0.50    --   93.70 -82.00   0.00   50
 35  \w     59.00 110.00   0.50    0.50    --   93.70 -59.00 120.00  102
 36  \w     13.00  92.00   0.50    0.50    --   93.70 -82.00  60.00  158
 37  \w     65.00 174.00   0.50    0.50    --   93.70  50.00 -60.00  218
 38  \w    112.00 180.00   0.50    0.50    --   93.70  42.00 -90.00  136
 39  \w      5.00  97.00   0.50    0.50    --   93.70 -82.00  30.00  184
 40  \w      4.00 107.00   0.50    0.50    --   93.70 -82.00  90.00  206
 41  \w     67.00 181.00   0.50    0.50    --   93.70  59.00 -30.00  228
 42  \w    102.00 129.00   0.50    0.50    --   93.70  42.00  60.00   54
 43  \w     87.00 112.00   0.50    0.50    --   93.70 -82.00 -73.16   50
 44  \w     33.00  74.00   0.50    0.50    --   93.70 -82.00 -73.16   82
;
_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      -0.0308425000
_diffrn_orient_matrix_UB_12      -0.1465956000
_diffrn_orient_matrix_UB_13      0.0042214000
_diffrn_orient_matrix_UB_21      0.0926086000
_diffrn_orient_matrix_UB_22      -0.0529027000
_diffrn_orient_matrix_UB_23      0.0127980000
_diffrn_orient_matrix_UB_31      0.0221984000
_diffrn_orient_matrix_UB_32      0.0145065000
_diffrn_orient_matrix_UB_33      0.0890786000
_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  0.0719
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26697
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.623
_diffrn_reflns_theta_min         2.873
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57799
_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_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0770P)^2^+0.4701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1857
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3023
_reflns_number_total             4919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01764d2.cif
_cod_data_source_block           m1_auto
_cod_database_code               7158970
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.767
_shelx_estimated_absorpt_t_min   0.678
_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 Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C00S(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010)
2.c Idealised Me refined as rotating group:
 C00W(H00F,H00G,H00H), C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,
 H01H,H01I)
;
_shelx_res_checksum              73400
_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 1.838
_oxdiff_exptl_absorpt_empirical_full_min 0.704