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_7161015
_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 H18 F3 N, C3 H7'
_chemical_formula_sum            'C26 H25 F3 N'
_chemical_formula_weight         408.47
_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             2024-11-02
_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                72.752(2)
_cell_angle_beta                 75.888(2)
_cell_angle_gamma                86.8218(17)
_cell_formula_units_Z            2
_cell_length_a                   9.0837(2)
_cell_length_b                   10.11921(18)
_cell_length_c                   12.4621(3)
_cell_measurement_reflns_used    10062
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.4730
_cell_measurement_theta_min      3.8110
_cell_volume                     1060.81(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (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      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.931
_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     59.00  89.00   0.50    0.05    --   62.21  15.00 150.00   60
  2  \w     56.00 102.00   0.50    0.05    --   62.21  15.00 120.00   92
  3  \w     62.00  97.00   0.50    0.05    --   62.21  15.00   0.00   70
  4  \w     58.00  83.00   0.50    0.05    --   62.21  15.00 -30.00   50
  5  \w     58.00 102.00   0.50    0.05    --   62.21  15.00 -90.00   88
  6  \w     55.00 103.00   0.50    0.05    --   62.21  15.00-120.00   96
  7  \w     72.00  98.00   0.50    0.05    --   62.21  15.00-150.00   52
  8  \w     69.00 102.00   0.50    0.05    --   62.21  15.00-180.00   66
  9  \w     57.00  82.00   0.50    0.05    --   62.21  15.00  30.00   50
 10  \w     67.00 115.00   0.50    0.05    --   74.33  15.00  60.00   96
 11  \w     69.00  94.00   0.50    0.05    --   71.27  15.00 120.00   50
 12  \w     65.00 107.00   0.50    0.05    --   71.27  15.00 150.00   84
 13  \w     67.00  92.00   0.50    0.05    --   74.33  15.00   0.00   50
 14  \w     76.00 101.00   0.50    0.05    --   74.33  15.00 -30.00   50
 15  \w     67.00 112.00   0.50    0.05    --   74.33  15.00 -60.00   90
 16  \w     74.00  99.00   0.50    0.05    --   74.33  15.00 -90.00   50
 17  \w     68.00  93.00   0.50    0.05    --   74.33  15.00-120.00   50
 18  \w     70.00 102.00   0.50    0.05    --   74.33  15.00-150.00   64
 19  \w     76.00 101.00   0.50    0.05    --   74.33  15.00-180.00   50
 20  \w     69.00  97.00   0.50    0.05    --   74.33  15.00  30.00   56
 21  \w     80.00 105.00   0.50    0.05    --   74.33  15.00  90.00   50
 22  \w     39.00  64.00   0.50    0.05    --   74.33-116.00 122.00   50
 23  \w     27.00  53.00   0.50    0.05    --   62.21-125.00 120.00   52
 24  \w     26.00  78.00   0.50    0.05    --   62.21-125.00  90.00  104
 25  \w     25.00  78.00   0.50    0.05    --   62.21-125.00  60.00  106
 26  \w     26.00  67.00   0.50    0.05    --   62.21-125.00   0.00   82
 27  \w     32.00  58.00   0.50    0.05    --   62.21-125.00 150.00   52
 28  \w     26.00  56.00   0.50    0.05    --   62.21-125.00 -30.00   60
 29  \w     49.00  78.00   0.50    0.05    --   62.21-125.00  30.00   58
 30  \w     35.00  87.00   0.50    0.05    --   71.27-125.00  30.00  104
 31  \w     41.00  83.00   0.50    0.05    --   71.27-125.00 -30.00   84
 32  \w     26.00  78.00   0.50    0.05    --   62.21-125.00 -60.00  104
 33  \w     46.00  74.00   0.50    0.05    --   62.21-125.00-120.00   56
 34  \w     49.00  87.00   0.50    0.05    --   71.27-125.00 -90.00   76
 35  \w     62.00  87.00   0.50    0.05    --   71.27-125.00-120.00   50
 36  \w     57.00  85.00   0.50    0.05    --   71.27-125.00-180.00   56
 37  \w     29.00  78.00   0.50    0.05    --   62.21-125.00-180.00   98
 38  \w     39.00  90.00   0.50    0.05    --   74.33-125.00-120.00  102
 39  \w     63.00  88.00   0.50    0.05    --   74.33-125.00-180.00   50
 40  \w     51.00  90.00   0.50    0.05    --   74.33-125.00 -60.00   78
 41  \w     46.00  90.00   0.50    0.05    --   74.33-125.00   0.00   88
 42  \w     46.00  90.00   0.50    0.05    --   74.33-125.00  60.00   88
 43  \w     44.00  70.00   0.50    0.05    --   74.33-125.00  90.00   52
 44  \w     58.00  89.00   0.50    0.05    --   74.33-125.00 150.00   62
 45  \w     48.00  81.00   0.50    0.05    --   71.27-116.00 122.00   66
 46  \w     53.00  90.00   0.50    0.05    --   74.33-125.00 120.00   74
 47  \w     65.00  90.00   0.50    0.05    --   74.33-125.00 -30.00   50
 48  \w     64.00  89.00   0.50    0.05    --   74.33-125.00 -90.00   50
 49  \w     46.00  90.00   0.50    0.05    --   74.33-125.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0837402000
_diffrn_orient_matrix_UB_12      0.0563240000
_diffrn_orient_matrix_UB_13      -0.1282636000
_diffrn_orient_matrix_UB_21      0.1492517000
_diffrn_orient_matrix_UB_22      -0.0611044000
_diffrn_orient_matrix_UB_23      0.0296926000
_diffrn_orient_matrix_UB_31      -0.0360915000
_diffrn_orient_matrix_UB_32      -0.1360657000
_diffrn_orient_matrix_UB_33      -0.0207853000
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14404
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.863
_diffrn_reflns_theta_min         3.824
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (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    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0546
_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^)+(0.1043P)^2^+0.4109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3621
_reflns_number_total             3950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00081a3.cif
_cod_data_source_block           97549_cf3
_cod_depositor_comments
'Adding full bibliography for 7161014--7161015.cif.'
_cod_original_cell_volume        1060.80(5)
_cod_database_code               7161015
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N  F'
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.908
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(H26C)=Sof(H26D)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H26A)=
 Sof(H26B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26C,H26D), C26(H26A,H26B), C27(H27A,H27B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C24(H24D,H24E,
 H24F)
;
_shelx_res_checksum              75102
_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 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.506