Brønsted acid-catalyzed cascade cyclization: an efficient strategy for divergent synthesis of cyclohepta[b]indole derivatives
Chen, Shaomin; Chen, Zhiyan; Zhang, Tianjian; Zhao, Bo; You, Bo; Li, Minghao; Gu, Yanlong; Green Chemistry 24 (2022) 7376–7381; doi:10.1039/D2GC02072F

data_7245545
_publ_section_title
;
 Br\/onsted acid-catalyzed cascade cyclization: an efficient strategy for
 divergent synthesis of cyclohepta[b]indole derivatives
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7376
_journal_page_last               7381
_journal_paper_doi               10.1039/D2GC02072F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H20 Cl N O2, C H Cl3'
_chemical_formula_sum            'C24 H21 Cl4 N O2'
_chemical_formula_weight         497.22
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-30 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.785(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8280(9)
_cell_length_b                   9.9575(4)
_cell_length_c                   16.1714(9)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5910
_cell_measurement_theta_min      3.0770
_cell_volume                     2275.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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   -102.00 -66.00   1.00    1.00    --  -40.73 141.00   4.00   36
  2  \w   -114.00 -25.00   1.00    1.00    --  -40.73 -38.00-150.00   89
  3  \w   -110.00 -29.00   1.00    1.00    --  -40.73 -38.00 120.00   81
  4  \w    120.00 177.00   1.00    2.00    --  107.58 125.00   0.00   57
  5  \w     79.00 175.00   1.00    2.00    --  107.58  30.00 120.00   96
  6  \w     81.00 174.00   1.00    2.00    --  107.58  30.00  30.00   93
  7  \w     71.00 118.00   1.00    2.00    --  107.58 -45.00  60.00   47
  8  \w     46.00 119.00   1.00    2.00    --  107.58-125.00  60.00   73
  9  \w     25.00  96.00   1.00    2.00    --  107.58 -95.00 -60.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0843156000
_diffrn_orient_matrix_UB_12      -0.0127739000
_diffrn_orient_matrix_UB_13      0.0969264000
_diffrn_orient_matrix_UB_21      0.0679349000
_diffrn_orient_matrix_UB_22      -0.0123187000
_diffrn_orient_matrix_UB_23      -0.0442150000
_diffrn_orient_matrix_UB_31      0.0126615000
_diffrn_orient_matrix_UB_32      0.1537390000
_diffrn_orient_matrix_UB_33      0.0045695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.128
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0866
_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^)+(0.1655P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2816
_reflns_number_total             4011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02072f2.cif
_cod_data_source_block           exp_4129
_cod_depositor_comments          'Adding full bibliography for 7245545.cif.'
_cod_database_code               7245545
_shelx_shelxl_version_number     2017/1
_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:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              74687
_olex2_date_sample_data_collection 2022-07-29
_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 2.663
_oxdiff_exptl_absorpt_empirical_full_min 0.479