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_7132405
_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         'C35 H30 N2 O2 S'
_chemical_formula_sum            'C35 H30 N2 O2 S'
_chemical_formula_weight         542.67
_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     dual
_audit_creation_date             2022-11-11
_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                 95.384(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.651(3)
_cell_length_b                   8.9231(12)
_cell_length_c                   22.780(3)
_cell_measurement_reflns_used    879
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      22.0130
_cell_measurement_theta_min      2.4430
_cell_volume                     2762.6(8)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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    -25.75 154.25   1.00    4.00 -25.75   0.00  73.76    --   180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0145354000
_diffrn_orient_matrix_UB_12      -0.0743729000
_diffrn_orient_matrix_UB_13      0.0075289000
_diffrn_orient_matrix_UB_21      0.0435730000
_diffrn_orient_matrix_UB_22      0.0095472000
_diffrn_orient_matrix_UB_23      -0.0143239000
_diffrn_orient_matrix_UB_31      0.0251924000
_diffrn_orient_matrix_UB_32      0.0262698000
_diffrn_orient_matrix_UB_33      0.0266500000
_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  0.1584
_diffrn_reflns_av_unetI/netI     0.1601
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14644
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20614
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.0979
_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^)+(0.1148P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2250
_refine_ls_wR_factor_ref         0.2881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2396
_reflns_number_total             4785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05237k2.cif
_cod_data_source_block           fastscan_autored
_cod_depositor_comments
'Adding full bibliography for 7132403--7132408.cif.'
_cod_original_cell_volume        2762.6(7)
_cod_database_code               7132405
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 79.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.54
_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:
 C008(H008), C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014)
2.d Idealised Me refined as rotating group:
 C00W(H00C,H00D,H00F), C00Z(H00H,H00I,H00K)
;
_shelx_res_checksum              37329
_shelx_hkl_checksum              9923
_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 2.463
_oxdiff_exptl_absorpt_empirical_full_min 0.457