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_7135578
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H21 N'
_chemical_formula_sum            'C20 H21 N'
_chemical_formula_weight         275.396
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-07-10
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9325(2)
_cell_length_b                   11.0390(4)
_cell_length_c                   19.2749(8)
_cell_measurement_reflns_used    9348
_cell_measurement_temperature    160.00
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.81
_cell_volume                     1475.07(9)
_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      160.00
_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 0.9866
_diffrn_measured_fraction_theta_max 0.9898
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0587
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.9866
_diffrn_reflns_Laue_measured_fraction_max 0.9898
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34507
_diffrn_reflns_point_group_measured_fraction_full 0.9892
_diffrn_reflns_point_group_measured_fraction_max 0.9916
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7312
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0817 after correction.
The Ratio of minimum to maximum transmission is 0.9628.
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    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             592.301
_exptl_crystal_recrystallization_method 'Slow evaporation from dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.2250
_refine_diff_density_min         -0.2058
_refine_diff_density_rms         0.0446
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.7(11)
_refine_ls_d_res_high            0.7567
_refine_ls_d_res_low             9.6374
_refine_ls_goodness_of_fit_ref   0.9503
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9503
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.994
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                3329
_reflns_number_total             3546
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc07212c2.cif
_cod_data_source_block           mo_JD180225_0m_a
_cod_depositor_comments
'Adding full bibliography for 7135578--7135579.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7135578
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C007(H00a,H00b), C00C(H00d,H00e), C00E(H00g,H00h), C00G(H00j,H00k), C00H(H00l,
 H00m), C00J(H00o,H00p)
2.b Aromatic/amide H refined with riding coordinates:
 C002(H002), C006(H006), C008(H008), C00A(H00c), C00D(H00f), C00F(H00i),
 C00I(H00n), C00K(H00q), C00L(H00r)
;
_olex2_submission_special_instructions 'No special instructions were received'