(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_7134836
_publ_section_title
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 (4 + 3) Annulation of Enone-Tethered Indoles with \a-Alkylidene
 Succinimides: Access to Seven-Membered Azepino[3,2,1-hi]Indole Scaffolds
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC02885J
_journal_year                    2025
_chemical_formula_moiety         'C34 H25 Br N2 O3'
_chemical_formula_sum            'C34 H25 Br N2 O3'
_chemical_formula_weight         589.47
_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             2024-05-29
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                101.9410(10)
_cell_angle_beta                 98.6800(10)
_cell_angle_gamma                112.7340(10)
_cell_formula_units_Z            2
_cell_length_a                   10.8312(4)
_cell_length_b                   11.1661(4)
_cell_length_c                   12.4253(5)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.78
_cell_volume                     1310.87(9)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47131
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.109
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0987 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9155.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0330P)^2^+0.8730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4283
_reflns_number_total             4606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02885j2.cif
_cod_data_source_block           rkp_rr_icsk_0748_0m
_cod_database_code               7134836
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.766
_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:
 C00A(H00A), C00B(H00B), C00L(H00L), C00O(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00C,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00N(H00N), C00Q(H00Q), C00U(H00U), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013)
;
_olex2_submission_special_instructions 'No special instructions were received'