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_7132407
_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      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             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                72.058(3)
_cell_angle_beta                 79.538(3)
_cell_angle_gamma                73.177(3)
_cell_formula_units_Z            4
_cell_length_a                   10.5565(3)
_cell_length_b                   17.7776(7)
_cell_length_c                   19.8243(8)
_cell_measurement_reflns_used    9529
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.9010
_cell_measurement_theta_min      2.1920
_cell_volume                     3370.5(2)
_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 0.973
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  \w    -81.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  200
  3  \w    -67.50 -13.00   0.50    8.00    --  -20.00 -72.00 108.00  109
;
_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      0.0656862000
_diffrn_orient_matrix_UB_12      -0.0186961000
_diffrn_orient_matrix_UB_13      0.0096044000
_diffrn_orient_matrix_UB_21      -0.0089425000
_diffrn_orient_matrix_UB_22      0.0262142000
_diffrn_orient_matrix_UB_23      0.0220893000
_diffrn_orient_matrix_UB_31      -0.0241649000
_diffrn_orient_matrix_UB_32      -0.0289637000
_diffrn_orient_matrix_UB_33      0.0291365000
_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  0.0555
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21697
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.096
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85420
_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    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     869
_refine_ls_number_reflns         11572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0443P)^2^+1.0511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7900
_reflns_number_total             11572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           sjg-negi-3-237_mo
_cod_depositor_comments
;
Adding full bibliography for 7132403--7132408.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C82 H70 N2 O8 S4'
_cod_original_formula_weight         1339.64
_cod_original_formula_moiety         '2(C41 H35 N O4 S2)'
_cod_original_formula_units_Z            2
_cod_database_code               7132407
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.960
_reflns_odcompleteness_completeness 82.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_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:
 C54(H54), C45(H45), C7(H7), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B), C43(H43A,H43B), C10(H10A,H10B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C72(H72), C60(H60), C35(H35), C63(H63), C73(H73), C82(H82), C62(H62),
 C22(H22), C61(H61), C12(H12), C34(H34), C31(H31), C74(H74), C21(H21), C13(H13),
  C15(H15), C20(H20), C79(H79), C78(H78), C32(H32), C69(H69), C38(H38),
 C76(H76), C19(H19), C48(H48), C29(H29), C37(H37), C33(H33), C68(H68), C81(H81),
  C27(H27), C80(H80), C16(H16), C75(H75), C49(H49), C50(H50), C52(H52),
 C39(H39), C28(H28), C65(H65), C66(H66), C41(H41), C51(H51), C40(H40), C25(H25),
  C26(H26)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C42(H42A,H42B,H42C), C70(H70A,H70B,H70C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              29667
_shelx_hkl_checksum              78672
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.612