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_7158969
_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 H20 N2 O S, C H Cl3'
_chemical_formula_sum            'C21 H21 Cl3 N2 O S'
_chemical_formula_weight         455.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-31
_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                 112.632(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4056(3)
_cell_length_b                   7.68510(10)
_cell_length_c                   13.5446(3)
_cell_measurement_reflns_used    5178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.3440
_cell_measurement_theta_min      3.5280
_cell_volume                     1095.81(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 0.994
_diffrn_measured_fraction_theta_max 0.992
_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    -39.00  15.00   0.50    0.50    --   42.30 -65.00 -60.00  108
  2  \w     45.00  70.00   0.50    0.50    --   42.30 -82.00  30.00   50
  3  \w    -33.00   4.00   0.50    0.50    --   42.30 -77.00  30.00   74
  4  \w     74.00 130.00   0.50    0.50    --   42.30  11.00  90.00  112
  5  \w      0.00  77.00   0.50    0.50    --   42.30 -32.00 -60.00  154
  6  \w     18.00  66.00   0.50    0.50    --   42.30 -77.00 -90.00   96
  7  \w    -34.00  68.00   0.50    0.50    --   42.30 -82.00 150.00  204
  8  \w     13.00  45.00   0.50    0.50    --   42.30 -77.00  30.00   64
  9  \w    -31.00  -6.00   0.50    0.50    --   42.30 -32.00 -60.00   50
 10  \w    -31.00  68.00   0.50    0.50    --   42.30 -77.00-180.00  198
 11  \w    -19.00   6.00   0.50    0.50    --   42.30 -82.00-150.00   50
 12  \w     16.00  59.00   0.50    0.50    --   42.30 -77.00  90.00   86
 13  \w     35.00  67.00   0.50    0.50    --   42.30 -82.00-150.00   64
 14  \w    -40.00  -8.00   0.50    0.50    --   42.30 -77.00 -90.00   64
 15  \w     -6.00  20.00   0.50    0.50    --   42.30  11.00  90.00   52
 16  \w     74.00  99.00   0.50    0.50    --   93.70 -82.00-150.00   50
 17  \w      4.00 183.00   0.50    0.50    --   93.70   0.00-120.00  358
 18  \w    145.00 183.00   0.50    0.50    --   93.70  50.00-180.00   76
 19  \w      4.00 128.00   0.50    0.50    --   93.70 -33.00-150.00  248
 20  \w     60.00  86.00   0.50    0.50    --   93.70 -82.00 -60.00   52
 21  \w     89.00 121.00   0.50    0.50    --   93.70 -33.00 -30.00   64
 22  \w     18.00  92.00   0.50    0.50    --   93.70 -82.00 -90.00  148
 23  \w     24.00  59.00   0.50    0.50    --   93.70 -82.00 -60.00   70
 24  \w     28.00  97.00   0.50    0.50    --   93.70 -82.00  30.00  138
 25  \w     55.00 111.00   0.50    0.50    --   93.70 -59.00 150.00  112
 26  \w      6.00  93.00   0.50    0.50    --   93.70 -82.00  90.00  174
 27  \w     18.00  43.00   0.50    0.50    --   93.70 -33.00 -30.00   50
 28  \w     11.00  37.00   0.50    0.50    --   93.70 -59.00 150.00   52
 29  \w     73.00  99.00   0.50    0.50    --   93.70 -82.00   0.00   52
 30  \w      9.00  63.00   0.50    0.50    --   93.70 -82.00 120.00  108
 31  \w     86.00 111.00   0.50    0.50    --   93.70 -82.00-180.00   50
 32  \w     19.00  62.00   0.50    0.50    --   93.70 -82.00   0.00   86
 33  \w     71.00  97.00   0.50    0.50    --   93.70 -82.00 120.00   52
 34  \w      6.00  82.00   0.50    0.50    --   93.70 -82.00-180.00  152
 35  \w    107.00 133.00   0.50    0.50    --   93.70  59.00 -60.00   52
 36  \w     19.00  86.00   0.50    0.50    --   93.70 -33.00 150.00  134
 37  \w     73.00  98.00   0.50    0.50    --   93.70 -82.00-120.00   50
 38  \w     31.00  91.00   0.50    0.50    --   93.70 -82.00 -30.00  120
 39  \w     38.00  80.00   0.50    0.50    --   93.70 -82.00  60.00   84
 40  \w      4.00 103.00   0.50    0.50    --   93.70 -82.00 145.35  198
;
_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      0.1430854000
_diffrn_orient_matrix_UB_12      0.0414664000
_diffrn_orient_matrix_UB_13      0.0436983000
_diffrn_orient_matrix_UB_21      0.0039282000
_diffrn_orient_matrix_UB_22      -0.0023139000
_diffrn_orient_matrix_UB_23      0.1149367000
_diffrn_orient_matrix_UB_31      0.0302089000
_diffrn_orient_matrix_UB_32      -0.1962305000
_diffrn_orient_matrix_UB_33      0.0078837000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9613
_diffrn_reflns_point_group_measured_fraction_full 0.703
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.191
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73285
_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    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0987P)^2^+0.3026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.307
_reflns_Friedel_fraction_full    0.360
_reflns_Friedel_fraction_max     0.357
_reflns_number_gt                2605
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01764d2.cif
_cod_data_source_block           mxtlbl2022051903_auto
_cod_original_cell_volume        1095.80(5)
_cod_database_code               7158969
_shelx_shelxl_version_number     2017/1
_diffrn_oxdiff_digest_frames
;
01dbcc61eaca1997555d2c738db835097900029c593
;
_diffrn_oxdiff_digest_hkl
;
01bb2aa49779aa56268de66440aadac907c39c
;
_reflns_odcompleteness_completeness 99.44
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00S(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00P(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00C(H00C), C00E(H00E), C00G(H00G), C00H(H00H), C00K(H00K),
 C00M(H00M), C00N(H00N)
2.d Idealised Me refined as rotating group:
 C00Q(H00I,H00L,H00O), C00R(H00P,H00Q,H00R)
2.e Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_shelx_res_checksum              76373
_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 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.755