(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_7134839
_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 O3'
_chemical_formula_sum            'C35 H27 Br N2 O3'
_chemical_formula_weight         603.49
_chemical_name_systematic        RKP_RR_A124_1419
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-26
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-10-26 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1417(3)
_cell_length_b                   8.8950(2)
_cell_length_c                   12.7012(3)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.53
_cell_volume                     1354.80(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0418
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27341
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.053
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_min         1.623
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1103 before and 0.0602 after correction. The Ratio of minimum to maximum transmission is 0.8645. 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    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_preparation
'Dissolved and refluxed in acetonitrile solvent'
_exptl_crystal_recrystallization_method
'Recrystallized via slow evaporation method in acetonitrile solvent'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.298(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.9030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4584
_reflns_number_total             4761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02885j2.cif
_cod_data_source_block           rkp_rr_a124_1419_0m
_cod_database_code               7134839
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.735
_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:
 C008(H008), C009(H009), C00F(H00F), C00Q(H00Q)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M),
 C00R(H00R), C00T(H00T), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015)
2.d Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C)
;
_shelx_res_checksum              3658
_shelx_hkl_checksum              69003
_olex2_submission_original_sample_id RKP_RR_A124_1419
_olex2_submission_special_instructions 'No special instructions were received'