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_7158967
_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_absolute_configuration ab
_chemical_formula_moiety         'C19 H16 N2 O S'
_chemical_formula_sum            'C19 H16 N2 O S'
_chemical_formula_weight         320.39
_chemical_name_systematic        1
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-06 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.94330(10)
_cell_length_b                   17.21630(10)
_cell_length_c                   18.86940(10)
_cell_measurement_reflns_used    19162
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9730
_cell_measurement_theta_min      2.3280
_cell_volume                     3230.19(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_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 0.998
_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     -9.00  66.00   0.50    0.52    --   42.30 -65.00  90.00  150
  2  \w     38.00 132.00   0.50    0.52    --   42.30  77.00-150.00  188
  3  \w     -3.00  27.00   0.50    0.52    --   42.30 -77.00  90.00   60
  4  \w     -4.00  69.00   0.50    0.52    --   42.30 -82.00-180.00  146
  5  \w     44.00  69.00   0.50    0.52    --   42.30 -82.00-120.00   50
  6  \w     14.00  41.00   0.50    0.52    --   42.30 -54.00 -60.00   54
  7  \w     47.00  73.00   0.50    0.52    --   42.30  65.00 -30.00   52
  8  \w     39.00  67.00   0.50    0.52    --   42.30  65.00-180.00   56
  9  \w     36.00  82.00   0.50    0.52    --   42.30  65.00 -90.00   92
 10  \w    -42.00 -12.00   0.50    0.52    --   42.30 -54.00 -60.00   60
 11  \w    -42.00 -13.00   0.50    0.52    --   42.30 -82.00-180.00   58
 12  \w    -24.00   1.00   0.50    0.52    --   42.30 -82.00-120.00   50
 13  \w    -37.00 -12.00   0.50    0.52    --   42.30 -65.00  90.00   50
 14  \w    -43.00  70.00   0.50    0.52    --   42.30 -82.00   0.00  226
 15  \w     17.00 132.00   0.50    0.52    --   42.30  54.00 -30.00  230
 16  \w     30.00  61.00   0.50    0.52    --   42.30 -77.00 -60.00   62
 17  \w     41.00  68.00   0.50    0.52    --   42.30 -77.00  90.00   54
 18  \w     78.00 128.00   0.50    0.52    --   42.30  65.00-180.00  100
 19  \w    -39.00 -14.00   0.50    0.52    --   42.30 -77.00  90.00   50
 20  \w      4.00  69.00   0.50    0.52    --   42.30 -82.00  60.00  130
 21  \w     59.00 182.00   0.50    1.00    --   93.70  33.00  60.00  246
 22  \w     38.00 114.00   0.50    1.00    --   93.70 -50.00-120.00  152
 23  \w     59.00 119.00   0.50    1.00    --   93.70 -42.00   0.00  120
 24  \w     73.00 101.00   0.50    1.00    --   93.70 -82.00 150.00   56
 25  \w      8.00  68.00   0.50    1.00    --   93.70 -82.00 150.00  120
 26  \w      4.00  34.00   0.50    1.00    --   93.70 -50.00-120.00   60
 27  \w     34.00 110.00   0.50    1.00    --   93.70 -82.00  30.00  152
 28  \w     45.00  96.00   0.50    1.00    --   93.70 -82.00  90.00  102
 29  \w     22.00  48.00   0.50    1.00    --   93.70 -42.00   0.00   52
 30  \w    145.00 170.00   0.50    1.00    --   93.70  33.00-120.00   50
 31  \w     25.00  97.00   0.50    1.00    --   93.70 -82.00-150.00  144
 32  \w     21.00  68.00   0.50    1.00    --   93.70 -82.00-180.00   94
 33  \w      6.00  34.00   0.50    1.00    --   93.70 -82.00  90.00   56
 34  \w      4.00  95.00   0.50    1.00    --   93.70 -82.00  60.00  182
 35  \w     40.00  96.00   0.50    1.00    --   93.70 -82.00   0.00  112
 36  \w    105.00 173.00   0.50    1.00    --   93.70  42.00 -60.00  136
 37  \w     99.00 162.00   0.50    1.00    --   93.70  68.00  90.00  126
 38  \w     44.00  92.00   0.50    1.00    --   93.70 -82.00 120.00   96
 39  \w     69.00  95.00   0.50    1.00    --   93.70 -82.00 -60.00   52
 40  \w     31.00 111.00   0.50    1.00    --   93.70 -82.00 -90.00  160
 41  \w    112.00 166.00   0.50    1.00    --   93.70  50.00 -30.00  108
 42  \w     64.00 165.00   0.50    1.00    --   93.70  33.00   0.00  202
 43  \w     68.00  98.00   0.50    1.00    --   93.70 -82.00 -30.00   60
 44  \w     73.00  98.00   0.50    1.00    --   93.70 -82.00-180.00   50
 45  \w      4.00  98.00   0.50    1.00    --   93.70 -82.00-120.00  188
;
_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      0.1293372000
_diffrn_orient_matrix_UB_12      -0.0360505000
_diffrn_orient_matrix_UB_13      -0.0306174000
_diffrn_orient_matrix_UB_21      0.0483703000
_diffrn_orient_matrix_UB_22      0.0812395000
_diffrn_orient_matrix_UB_23      -0.0228128000
_diffrn_orient_matrix_UB_31      0.0702655000
_diffrn_orient_matrix_UB_32      0.0104234000
_diffrn_orient_matrix_UB_33      0.0721588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31960
_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         68.205
_diffrn_reflns_theta_min         3.475
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55025
_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 blackish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.015(16)
_refine_ls_extinction_coef       0.0050(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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0537P)^2^+0.1524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5593
_reflns_number_total             5865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01764d2.cif
_cod_data_source_block           zj20210426_auto
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H32 N4 O2 S2'
_cod_original_formula_weight         640.79
_cod_original_formula_moiety         '2(C19 H16 N2 O S)'
_cod_original_formula_units_Z            4
_cod_database_code               7158967
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.899
_diffrn_oxdiff_digest_frames
;
01306a6a4f7d41633db7d1dafb3efbb0da00028ff4a
;
_diffrn_oxdiff_digest_hkl
;
0142b8cb57d44e4a9609a76cb15ce2b6b331e3
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.015(16)
 -0.015(16)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 N44(H44), N21(H21), C27(H27), C4(H4), C39(H39), C6(H6), C7(H7), C42(H42),
 C16(H16), C17(H17), C40(H40), C19(H19), C29(H29), C41(H41), C30(H30), C18(H18)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              54485
_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 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.582