A concise synthesis of indole-fused azepino- and azocino-indoles <i>via</i> acid-catalyzed 1,2-migration.
Parui, Nabin; Maji, Kousik; Diasi, Manab; Dash, Jyotirmayee; Chemical communications (Cambridge, England) 62 (2026) 6746–6750; doi:10.1039/d5cc07212c

data_7135579
_publ_section_title
;
 A concise synthesis of indole-fused azepino- and azocino-indoles
 <i>via</i> acid-catalyzed 1,2-migration.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6746
_journal_page_last               6750
_journal_paper_doi               10.1039/d5cc07212c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         '2(C19 H18 F N)'
_chemical_formula_sum            'C38 H36 F2 N2'
_chemical_formula_weight         558.720
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-09-18 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                102.430(6)
_cell_angle_beta                 95.802(6)
_cell_angle_gamma                90.091(6)
_cell_formula_units_Z            2
_cell_length_a                   8.1550(13)
_cell_length_b                   12.2573(19)
_cell_length_c                   14.773(2)
_cell_measurement_reflns_used    5927
_cell_measurement_temperature    139.99
_cell_measurement_theta_max      34.00
_cell_measurement_theta_min      3.07
_cell_volume                     1434.3(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      139.99
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.9588
_diffrn_measured_fraction_theta_max 0.7930
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_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  0.0805
_diffrn_reflns_av_unetI/netI     0.1255
_diffrn_reflns_Laue_measured_fraction_full 0.9588
_diffrn_reflns_Laue_measured_fraction_max 0.7930
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19064
_diffrn_reflns_point_group_measured_fraction_full 0.9588
_diffrn_reflns_point_group_measured_fraction_max 0.7930
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         34.64
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.3285
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1588 before and 0.0935 after correction.
The Ratio of minimum to maximum transmission is 0.4399.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             592.364
_exptl_crystal_recrystallization_method 'Slow evaporation from DCM'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.9476
_refine_diff_density_min         -1.0511
_refine_diff_density_rms         0.2393
_refine_ls_d_res_high            0.6252
_refine_ls_d_res_low             8.3442
_refine_ls_goodness_of_fit_ref   1.1471
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1471
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.1217
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2924
_refine_ls_wR_factor_ref         0.3648
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              -18
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                5757
_reflns_number_total             9745
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc07212c2.cif
_cod_data_source_block           ANS
_cod_depositor_comments
'Adding full bibliography for 7135578--7135579.cif.'
_cod_database_code               7135579
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'