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_7132404
_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         'C41 H35 N O4 S2'
_chemical_formula_sum            'C41 H35 N O4 S2'
_chemical_formula_weight         669.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-22
_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                90
_cell_angle_beta                 113.210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4285(18)
_cell_length_b                   11.6342(8)
_cell_length_c                   16.4121(14)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.3900
_cell_measurement_theta_min      2.2090
_cell_volume                     3409.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00-108.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0063680000
_diffrn_orient_matrix_UB_12      -0.0389465000
_diffrn_orient_matrix_UB_13      -0.0295477000
_diffrn_orient_matrix_UB_21      0.0371469000
_diffrn_orient_matrix_UB_22      0.0208556000
_diffrn_orient_matrix_UB_23      0.0133665000
_diffrn_orient_matrix_UB_31      0.0125524000
_diffrn_orient_matrix_UB_32      -0.0420096000
_diffrn_orient_matrix_UB_33      0.0340475000
_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  0.0729
_diffrn_reflns_av_unetI/netI     0.1234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11500
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.089
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1357P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3394
_reflns_number_total             5992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           sjg-negi-4-332_mo
_cod_depositor_comments
'Adding full bibliography for 7132403--7132408.cif.'
_cod_original_cell_volume        3409.5(5)
_cod_database_code               7132404
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 87.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_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 Ternary CH refined with riding coordinates:
 C00A(H00A), C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00B,H00C), C00X(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C010(H010), C011(H011), C013(H013), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C019(H019), C01A(H01D), C01C(H01H)
2.d Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C01B(H01E,H01F,H01G)
;
_shelx_res_checksum              46086
_shelx_hkl_checksum              22994
_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 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.691