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_7132403
_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         'C36 H33 N O2 S'
_chemical_formula_sum            'C36 H33 N O2 S'
_chemical_formula_weight         543.69
_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             2018-08-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-09-22 deposited with the CCDC.	2023-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                68.202(3)
_cell_angle_beta                 71.011(3)
_cell_angle_gamma                87.557(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0196(3)
_cell_length_b                   11.9729(3)
_cell_length_c                   12.4127(3)
_cell_measurement_reflns_used    9116
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1570
_cell_measurement_theta_min      2.1840
_cell_volume                     1432.13(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  19.00   0.50    8.00    --  -20.00 -72.00-108.00  258
  2  \w    -87.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  212
  3  \w    -41.00  70.00   0.50    8.00    --  -20.00   0.00  36.00  222
  4  \w    -35.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  108
;
_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      0.0038392000
_diffrn_orient_matrix_UB_12      0.0630901000
_diffrn_orient_matrix_UB_13      -0.0334394000
_diffrn_orient_matrix_UB_21      0.0153684000
_diffrn_orient_matrix_UB_22      0.0110932000
_diffrn_orient_matrix_UB_23      0.0465693000
_diffrn_orient_matrix_UB_31      0.0664824000
_diffrn_orient_matrix_UB_32      -0.0003416000
_diffrn_orient_matrix_UB_33      -0.0312304000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.515
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93735
_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    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0438P)^2^+0.6899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4349
_reflns_number_total             5021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           sjg-negi-3-271-3_mo
_cod_depositor_comments
'Adding full bibliography for 7132403--7132408.cif.'
_cod_original_cell_volume        1432.12(8)
_cod_database_code               7132403
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 89.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.03
_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:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C32(H32), C6(H6), C33(H33), C22(H22), C31(H31), C23(H23),
 C29(H29), C18(H18), C19(H19), C15(H15), C4(H4), C30(H30), C5(H5), C16(H16),
 C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C20(H20A,H20B,H20C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              66741
_shelx_hkl_checksum              96807
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.426
_oxdiff_exptl_absorpt_empirical_full_min 0.788