Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles
Liu, Tingting; Wang, Jianbin; Xiao, Rou; Zhao, Junling; RSC Advances 14 (2024) 15591–15596; doi:10.1039/D4RA03231D

data_7248607
_publ_section_title
;
 Switchable divergent synthesis of chiral indole derivatives via catalytic
 asymmetric dearomatization of 2,3-disubstituted indoles
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              15591
_journal_page_last               15596
_journal_paper_doi               10.1039/D4RA03231D
_journal_volume                  14
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H26 N2 O3 S'
_chemical_formula_sum            'C28 H26 N2 O3 S'
_chemical_formula_weight         470.57
_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     dual
_audit_creation_date             2023-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-03-30 deposited with the CCDC.	2024-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.87694(13)
_cell_length_b                   11.7651(2)
_cell_length_c                   22.7128(3)
_cell_measurement_reflns_used    14168
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.1650
_cell_measurement_theta_min      3.9030
_cell_volume                     2372.08(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -62.00 -35.00   0.50    0.22    -- -100.00  61.00 120.00   54
  2  \w    -69.00 -26.00   0.50    0.22    -- -100.00  61.00   0.00   86
  3  \w    -61.00 -36.00   0.50    0.22    -- -100.00  61.00 -90.00   50
  4  \w     -5.00  34.00   0.50    0.05    --  -44.59  19.00-180.00   78
  5  \w    -28.00  72.00   0.50    0.05    --   44.59 -85.00  71.00  200
  6  \w    -17.00   9.00   0.50    0.05    --  -44.59  19.00 -60.00   52
  7  \w    -73.00 -47.00   0.50    0.05    --  -44.59 125.00-120.00   52
  8  \w   -160.00 -81.00   0.50    0.22    -- -100.00 -85.00  71.00  158
  9  \w     33.00  60.00   0.50    0.22    --  105.85 -77.00 120.00   54
 10  \w     35.00  71.00   0.50    0.22    --  105.85 -61.00 150.00   72
 11  \w     80.00 107.00   0.50    0.22    --  105.85 -77.00 120.00   54
 12  \w    113.00 161.00   0.50    0.22    --  105.85  47.00  69.00   96
 13  \w     90.00 152.00   0.50    0.22    --  105.85  95.00 -72.00  124
 14  \w     44.00  72.00   0.50    0.22    --  105.85 -61.00-180.00   56
 15  \w     42.00  69.00   0.50    0.22    --  105.85 -61.00-150.00   54
 16  \w     84.00 110.00   0.50    0.22    --  112.25 135.00  33.00   52
 17  \w   -118.00 -93.00   0.50    0.05    --  -44.84-135.00 146.00   50
 18  \w    -13.00  25.00   0.50    0.05    --  -44.84  19.00-120.00   76
 19  \w     76.00 113.00   0.50    0.05    --   44.84  57.00-120.00   74
 20  \w     32.00  65.00   0.50    0.05    --   44.84  57.00-120.00   66
 21  \w     43.00  89.00   0.50    0.22    --  112.25 -94.00-150.00   92
 22  \w     43.00 109.00   0.50    0.22    --  112.25-125.00 -30.00  132
 23  \w    102.00 128.00   0.50    0.22    --  112.25  30.00 -30.00   52
 24  \w     84.00 110.00   0.50    0.22    --  112.25-125.00 -60.00   52
 25  \w     93.00 119.00   0.50    0.22    --  112.25-135.00  56.00   52
 26  \w     55.00 111.00   0.50    0.22    --  112.25-125.00-180.00  112
 27  \w     42.00  67.00   0.50    0.22    --  112.25-135.00  56.00   50
 28  \w     55.00  97.00   0.50    0.22    --  112.25 -94.00-120.00   84
 29  \w    120.00 178.00   0.50    0.22    --  112.25  61.00 -60.00  116
 30  \w     77.00 103.00   0.50    0.22    --  112.25 -94.00-180.00   52
 31  \w    100.00 164.00   0.50    0.22    --  112.25  61.00 -90.00  128
 32  \w    144.00 173.00   0.50    0.22    --  112.25  30.00 -30.00   58
 33  \w     93.00 119.00   0.50    0.22    --  112.25-135.00 146.00   52
 34  \w     84.00 110.00   0.50    0.22    --  112.25-125.00-150.00   52
 35  \w     58.00  84.00   0.50    0.22    --  112.25 -94.00 -30.00   52
 36  \w    120.00 146.00   0.50    0.22    --  112.25 135.00  33.00   52
 37  \w     19.00 118.00   0.50    0.05    --   44.84  77.00   0.00  198
 38  \w     19.00 118.00   0.50    0.05    --   44.84  77.00 -90.00  198
 39  \w     19.00 118.00   0.50    0.05    --   44.84  77.00 120.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1015242000
_diffrn_orient_matrix_UB_12      0.0739105000
_diffrn_orient_matrix_UB_13      -0.0394492000
_diffrn_orient_matrix_UB_21      -0.1152527000
_diffrn_orient_matrix_UB_22      0.0976683000
_diffrn_orient_matrix_UB_23      0.0036937000
_diffrn_orient_matrix_UB_31      0.0806582000
_diffrn_orient_matrix_UB_32      0.0464661000
_diffrn_orient_matrix_UB_33      0.0550473000
_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  0.0505
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23451
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.565
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0598P)^2^+0.4128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                4544
_reflns_number_total             4847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra03231d2.cif
_cod_data_source_block           lintt_230411_auto
_cod_original_cell_volume        2372.08(7)
_cod_database_code               7248607
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     CHONSCl
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00D), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C), C00R(H00E,H00F,H00G), C00X(H00H,H00I,H00K), C00Y(H00R,
 H00W,H00X)
;
_shelx_res_checksum              30442
_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 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.564