(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_7134837
_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         'C35 H27 Br N2 O4'
_chemical_formula_sum            'C35 H27 Br N2 O4'
_chemical_formula_weight         619.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                99.1960(10)
_cell_angle_beta                 98.7160(10)
_cell_angle_gamma                109.2330(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1577(2)
_cell_length_b                   10.7731(2)
_cell_length_c                   13.5579(2)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.18
_cell_volume                     1349.24(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0513
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            65350
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         1.559
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0566 after correction. The Ratio of minimum to maximum transmission is 0.9298. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_preparation
'refluxed in acetonitrile and left for slow evaporation'
_exptl_crystal_recrystallization_method
'slow evaporation in acetonitrile solvent'
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.8850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4451
_reflns_number_total             4756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02885j2.cif
_cod_data_source_block           rkp_rr_a86_1144_0m
_cod_database_code               7134837
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.844
_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:
 C00C(H00C), C00G(H00G), C00L(H00L), C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00O(H00O),
 C00R(H00R), C00T(H00T), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015)
2.d Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C)
;
_shelx_res_checksum              47490
_shelx_hkl_checksum              93237
_olex2_submission_original_sample_id RKP_RR_A86_1144
_olex2_submission_special_instructions 'No special instructions were received'