Cascade radical cyclization on 3-propargyl-2-alkenyl indole gives stereoselective access to cyclohepta[<i>b</i>]indole over carbazole.
Gharpure, Santosh J.; Kumari, Sanyog; Chemical communications (Cambridge, England) 60 (2024) 538–541; doi:10.1039/d3cc05237k

data_7132406
_publ_section_title
;
 Cascade radical cyclization on 3-propargyl-2-alkenyl indole gives
 stereoselective access to cyclohepta[<i>b</i>]indole over carbazole.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              538
_journal_page_last               541
_journal_paper_doi               10.1039/d3cc05237k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C32 H25 N S'
_chemical_formula_sum            'C32 H25 N S'
_chemical_formula_weight         455.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-09-22 deposited with the CCDC.	2023-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                95.743(6)
_cell_angle_beta                 112.337(6)
_cell_angle_gamma                116.102(6)
_cell_formula_units_Z            2
_cell_length_a                   10.4151(5)
_cell_length_b                   11.5788(8)
_cell_length_c                   12.6011(9)
_cell_measurement_reflns_used    4565
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      25.1610
_cell_measurement_theta_min      1.8470
_cell_volume                     1195.11(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -20.08 339.92   1.00    2.00 -25.84   0.00  59.25    --   360
  2  \w     -1.00  46.00   1.00    2.00    --    0.00 -94.56-145.16   47
  3  \w    -71.47  -9.47   1.00    2.00    --  -17.90 107.43  -1.09   62
  4  \w    -90.97  25.03   1.00    2.00    --    0.00 -59.25 164.08  116
  5  \w    -90.97  25.03   1.00    2.00    --    0.00 -59.25  92.08  116
  6  \w    -90.97  25.03   1.00    2.00    --    0.00 -59.25 -51.92  116
  7  \w    -90.97  25.03   1.00    2.00    --    0.00 -59.25  20.08  116
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0082686000
_diffrn_orient_matrix_UB_12      -0.0438966000
_diffrn_orient_matrix_UB_13      0.0355725000
_diffrn_orient_matrix_UB_21      -0.0857622000
_diffrn_orient_matrix_UB_22      -0.0331789000
_diffrn_orient_matrix_UB_23      -0.0339146000
_diffrn_orient_matrix_UB_31      -0.0003364000
_diffrn_orient_matrix_UB_32      -0.0465086000
_diffrn_orient_matrix_UB_33      -0.0414182000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34821
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.845
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.005(2)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0709P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2994
_reflns_number_total             4207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           sjg_negi_03_267_autored
_cod_depositor_comments
'Adding full bibliography for 7132403--7132408.cif.'
_cod_original_cell_volume        1195.11(15)
_cod_database_code               7132406
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 65.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.02
_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:
 C00A(H00A), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X)
2.b Idealised Me refined as rotating group:
 C00P(H00B,H00C,H00F), C00Y(H00K,H00P,H00Y)
;
_shelx_res_checksum              94571
_shelx_hkl_checksum              37078
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.644