Substrate-controlled divergent synthesis of substituted carbazoles through a cascade reaction of 2-alkenylindoles with α,β-unsaturated ketones.
Yang, Shizhou; Wang, Mingliang; Jiang, Hong; Wang, Rui; Xing, Yurou; Luo, Shuang; Ding, Qinlin; Organic & biomolecular chemistry 24 (2026) 2415–2422; doi:10.1039/d6ob00081a

data_7161014
_publ_section_title
;
 Substrate-controlled divergent synthesis of substituted carbazoles
 through a cascade reaction of 2-alkenylindoles with
 &#x3b1;,&#x3b2;-unsaturated ketones.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2415
_journal_page_last               2422
_journal_paper_doi               10.1039/d6ob00081a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C23 H17 F4 N'
_chemical_formula_sum            'C23 H17 F4 N'
_chemical_formula_weight         383.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-04-15
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-05-07 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                74.496(4)
_cell_angle_beta                 87.854(4)
_cell_angle_gamma                65.355(4)
_cell_formula_units_Z            4
_cell_length_a                   9.9386(5)
_cell_length_b                   11.3326(5)
_cell_length_c                   18.1315(9)
_cell_measurement_reflns_used    15561
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4530
_cell_measurement_theta_min      2.5300
_cell_volume                     1782.19(17)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.942
_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     33.00 120.00   0.50    0.05    --   43.18  38.00-180.00  174
  2  \w    130.00 167.00   0.50    0.05    --  106.94  30.00 -30.00   74
  3  \w     94.00 120.00   0.50    0.05    --  106.94  30.00 -30.00   52
  4  \w     93.00 137.00   0.50    0.05    --  106.94  15.00-180.00   88
  5  \w     94.00 120.00   0.50    0.05    --  106.94  30.00  60.00   52
  6  \w    110.00 138.00   0.50    0.05    --  106.94  15.00  30.00   56
  7  \w    136.00 169.00   0.50    0.05    --  106.94  30.00  60.00   66
  8  \w     94.00 139.00   0.50    0.05    --  106.94  15.00 120.00   90
  9  \w     96.00 123.00   0.50    0.05    --  106.94  15.00 150.00   54
 10  \w     33.00  74.00   0.50    0.05    --  106.94 -77.00  30.00   82
 11  \w     37.00  64.00   0.50    0.05    --  106.94 -77.00 120.00   54
 12  \w    105.00 130.00   0.50    0.05    --  106.94 130.00 -97.00   50
 13  \w     52.00  77.00   0.50    0.05    --  106.94 -77.00-120.00   50
 14  \w     61.00  86.00   0.50    0.05    --   43.18-130.00-169.00   50
 15  \w     64.00  90.00   0.50    0.05    --  106.94-130.00-169.00   52
 16  \w     48.00  96.00   0.50    0.05    --  106.94-126.00-150.00   96
 17  \w     36.00  69.00   0.50    0.05    --  106.94-126.00-120.00   66
 18  \w     63.00  88.00   0.50    0.05    --  106.94 -95.00  30.00   50
 19  \w     44.00  89.00   0.50    0.05    --  106.94 -95.00  90.00   90
 20  \w     58.00  92.00   0.50    0.05    --  106.94 -95.00 150.00   68
 21  \w    -14.00  27.00   0.50    0.05    --  -43.18  38.00   0.00   82
 22  \w     -7.00  33.00   0.50    0.05    --  -43.18  38.00  30.00   80
 23  \w    -62.00  24.00   0.50    0.05    --  -43.18  77.00  60.00  172
 24  \w     -3.00  31.00   0.50    0.05    --  -43.18  38.00 -30.00   68
 25  \w    -41.00  31.00   0.50    0.05    --  -43.18  57.00 -60.00  144
 26  \w    -85.00 -20.00   0.50    0.05    --  -43.18 130.00 -97.00  130
 27  \w    -77.00 -51.00   0.50    0.05    -- -103.00 130.00 -97.00   52
 28  \w    -96.00 -40.00   0.50    0.05    -- -103.00 114.00 -61.90  112
 29  \w    -96.00 -71.00   0.50    0.05    -- -103.00 114.00-161.15   50
 30  \w    -97.00 -33.00   0.50    0.05    -- -103.00 114.00 -35.40  128
 31  \w    -68.00 -42.00   0.50    0.05    -- -103.00 114.00-161.15   52
 32  \w    -97.00 -32.00   0.50    0.05    -- -103.00 114.00  55.29  130
 33  \w    -63.00 -31.00   0.50    0.05    -- -103.00 126.00  60.00   64
 34  \w   -101.00 -70.00   0.50    0.05    -- -103.00 126.00  60.00   62
 35  \w    -93.00 -66.00   0.50    0.05    -- -103.00 102.00 -52.46   54
 36  \w    -93.00 -29.00   0.50    0.05    -- -103.00 102.00 -85.36  128
 37  \w    -84.00 -31.00   0.50    0.05    -- -103.00 114.00-169.41  106
 38  \w    -64.00 -37.00   0.50    0.05    -- -103.00  77.00 -90.00   54
 39  \w    -89.00 -32.00   0.50    0.05    -- -103.00 106.00  -8.29  114
 40  \w    -91.00 -65.00   0.50    0.05    -- -103.00 101.00  54.20   52
 41  \w    -97.00 -72.00   0.50    0.05    -- -103.00 114.00 150.60   50
 42  \w   -131.00 -92.00   0.50    0.05    -- -103.00 -15.00  30.00   78
 43  \w   -122.00 -88.00   0.50    0.05    -- -103.00 -15.00   0.00   68
 44  \w   -133.00 -89.00   0.50    0.05    -- -103.00 -15.00 -60.00   88
 45  \w   -131.00 -92.00   0.50    0.05    -- -103.00 -15.00-120.00   78
 46  \w   -129.00 -99.00   0.50    0.05    -- -103.00 -15.00-150.00   60
 47  \w   -118.00 -79.00   0.50    0.05    --  -43.18 -38.00-120.00   78
 48  \w   -134.00-109.00   0.50    0.05    -- -103.00-130.00-169.00   50
 49  \w   -169.00-114.00   0.50    0.05    -- -103.00 -95.00  60.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1091347000
_diffrn_orient_matrix_UB_12      0.0060575000
_diffrn_orient_matrix_UB_13      -0.0605511000
_diffrn_orient_matrix_UB_21      0.0768356000
_diffrn_orient_matrix_UB_22      0.0613609000
_diffrn_orient_matrix_UB_23      -0.0644346000
_diffrn_orient_matrix_UB_31      0.1071433000
_diffrn_orient_matrix_UB_32      -0.1429277000
_diffrn_orient_matrix_UB_33      -0.0035237000
_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  0.0172
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18902
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.568
_diffrn_reflns_theta_min         2.538
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6892
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0443P)^2^+1.1666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6772
_reflns_number_total             6892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00081a3.cif
_cod_data_source_block           975490
_cod_depositor_comments
'Adding full bibliography for 7161014--7161015.cif.'
_cod_original_cell_volume        1782.20(16)
_cod_database_code               7161014
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C  H O N F'
_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. Rigid body (RIGU) restrains
 C35, C37, C36, C34
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C26(H26), C27(H27), C32(H32), C39(H39), C40(H40), C41(H41), C42(H42),
  C43(H43), C46(H46)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C45(H45A,H45B,
 H45C)
;
_shelx_res_checksum              21837
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.553