(4 + 3) Annulation of Enone-Tethered Indoles with α-Alkylidene Succinimides: Access to Seven-Membered Azepino[3,2,1-hi]Indole Scaffolds
Raza, Mohammad Saim; Roshani, K. M.; Peddinti, Rama Krishna; Chemical Communications  (2025) –; doi:10.1039/D5CC02885J

data_7134838
_publ_section_title
;
 (4 + 3) Annulation of Enone-Tethered Indoles with \a-Alkylidene
 Succinimides: Access to Seven-Membered Azepino[3,2,1-hi]Indole Scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC02885J
_journal_year                    2025
_chemical_formula_moiety         'C32 H24 Br N2 O3 S'
_chemical_formula_sum            'C32 H24 Br N2 O3 S'
_chemical_formula_weight         596.50
_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             2024-10-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-10-01 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8268(2)
_cell_length_b                   11.8871(2)
_cell_length_c                   20.0235(4)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.55
_cell_volume                     2576.17(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      100.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58673
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.053
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_min         1.993
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1402 before and 0.0466 after correction. The Ratio of minimum to maximum transmission is 0.8735. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_preparation
'Refluxed in acetonitrile solvent and then left for slow evaporation'
_exptl_crystal_recrystallization_method
'Slow evaporation in acetonitrile solvent'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0760P)^2^+2.0450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4350
_reflns_number_total             4505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02885j2.cif
_cod_data_source_block           rkp_rr_a78_1084_0m
_cod_database_code               7134838
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.713
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00G), C010(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013)
;
_shelx_res_checksum              85345
_shelx_hkl_checksum              77351
_olex2_submission_original_sample_id RKP_RR_A78_1084
_olex2_submission_special_instructions 'No special instructions were received'