Electrochemical synthesis of γ-carbolinones <i>via</i> sulfonylation-triggered cyclization of indole-3-carboxamides.
Luo, Dan; Wang, Qian; Liu, Jiang; Mei, Haibo; Han, Jianlin; Organic & biomolecular chemistry 23 (2025) 1309–1313; doi:10.1039/d4ob01703j

data_7160286
_publ_section_title
;
 Electrochemical synthesis of &#x3b3;-carbolinones <i>via</i>
 sulfonylation-triggered cyclization of indole-3-carboxamides.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1309
_journal_page_last               1313
_journal_paper_doi               10.1039/d4ob01703j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H21 F N2 O5 S'
_chemical_formula_sum            'C22 H21 F N2 O5 S'
_chemical_formula_weight         444.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-07-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-10-08 deposited with the CCDC.	2024-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0126(2)
_cell_length_b                   10.5943(2)
_cell_length_c                   19.0839(3)
_cell_measurement_reflns_used    10975
_cell_measurement_temperature    100.00(10)
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_cell_measurement_theta_min      4.2250
_cell_volume                     2014.10(6)
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_computing_data_collection
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.973
_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    -15.00  11.00   0.50    0.10    --   45.87 -78.00  96.00   52
  2  \w     27.00 112.00   0.50    0.10    --   99.00 -78.00  96.00  170
  3  \w     29.00  73.00   0.50    0.10    --   99.00 -61.00  30.00   88
  4  \w     28.00  54.00   0.50    0.10    --   99.00 -61.00 120.00   52
  5  \w     29.00  65.00   0.50    0.10    --   99.00 -61.00   0.00   72
  6  \w     28.00  53.00   0.50    0.10    --   99.00 -45.00 -30.00   50
  7  \w     27.00  52.00   0.50    0.10    --   99.00 -45.00 -60.00   50
  8  \w    -22.00  28.00   0.50    0.10    --   45.87 -19.00  90.00  100
  9  \w     26.00 108.00   0.50    0.10    --   99.00 -77.00 -90.00  164
 10  \w     27.00  52.00   0.50    0.10    --   99.00 -45.00-120.00   50
 11  \w     27.00  52.00   0.50    0.10    --   99.00 -45.00-180.00   50
 12  \w    124.00 150.00   0.50    0.10    --   99.00  78.00-138.00   52
 13  \w    100.00 126.00   0.50    0.10    --   99.00 125.00 -60.00   52
 14  \w    135.00 161.00   0.50    0.10    --   99.00 125.00 -60.00   52
 15  \w     57.00 104.00   0.50    0.10    --   99.00 -94.00  30.00   94
 16  \w    -19.00  16.00   0.50    0.10    --  -45.87  37.00-180.00   70
 17  \w    -52.00  27.00   0.50    0.10    --  -45.87  78.00-138.00  158
 18  \w    -14.00  12.00   0.50    0.10    --  -45.87  19.00 -60.00   52
 19  \w    -40.00  26.00   0.50    0.10    --  -45.87  37.00 -30.00  132
 20  \w    -77.00 -27.00   0.50    0.10    --  -99.00  78.00-138.00  100
 21  \w    -68.00 -43.00   0.50    0.10    --  -99.00  61.00-150.00   50
 22  \w    -65.00 -31.00   0.50    0.10    --  -99.00  61.00-180.00   68
 23  \w    -68.00 -26.00   0.50    0.10    --  -99.00  61.00 -30.00   84
 24  \w   -175.00 -81.00   0.50    0.10    --  -99.00 -15.00 150.00  188
 25  \w   -174.00-137.00   0.50    0.10    --  -99.00 -30.00 120.00   74
 26  \w   -121.00 -95.00   0.50    0.10    --  -99.00 -30.00 120.00   52
 27  \w   -153.00 -97.00   0.50    0.10    --  -99.00 -78.00  96.00  112
;
_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      -0.0909701000
_diffrn_orient_matrix_UB_12      -0.1137008000
_diffrn_orient_matrix_UB_13      0.0119096000
_diffrn_orient_matrix_UB_21      -0.1008120000
_diffrn_orient_matrix_UB_22      0.0444789000
_diffrn_orient_matrix_UB_23      -0.0613550000
_diffrn_orient_matrix_UB_31      0.0740747000
_diffrn_orient_matrix_UB_32      -0.0788843000
_diffrn_orient_matrix_UB_33      -0.0517614000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.321
_diffrn_reflns_theta_min         4.658
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00090(12)
_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   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0474P)^2^+0.8674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3675
_reflns_number_total             3937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01703j2.cif
_cod_data_source_block           ld_1
_cod_depositor_comments          'Adding full bibliography for 7160286.cif.'
_cod_database_code               7160286
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S F'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              35542
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.787