Synthesis of benzimidazole-fused 1,4-benzoxazepines and benzosultams spiro-connected to a 2-oxindole core <i>via</i> a tandem epoxide-opening/S<sub>N</sub>Ar approach.
Gogoi, Abhijit; Mukhopadhyay, Subhamoy; Chouhan, Raju; Das, Sajal Kumar; Organic & biomolecular chemistry 22 (2024) 353–363; doi:10.1039/d3ob01613g

data_7159744
_publ_section_title
;
 Synthesis of benzimidazole-fused 1,4-benzoxazepines and benzosultams
 spiro-connected to a 2-oxindole core <i>via</i> a tandem
 epoxide-opening/S<sub>N</sub>Ar approach.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              353
_journal_page_last               363
_journal_paper_doi               10.1039/d3ob01613g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H16 Br N3 O2'
_chemical_formula_sum            'C23 H16 Br N3 O2'
_chemical_formula_weight         446.30
_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
_audit_creation_date             2023-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                78.499(2)
_cell_angle_beta                 83.899(2)
_cell_angle_gamma                89.971(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8245(7)
_cell_length_b                   12.5840(10)
_cell_length_c                   17.0500(14)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.32
_cell_volume                     1844.4(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6438
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.652
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6075
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0887 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.8147.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       cube
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.339
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         6438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0454P)^2^+5.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5657
_reflns_number_total             6438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01613g2.cif
_cod_data_source_block           ag108
_cod_depositor_comments
'Adding full bibliography for 7159744--7159745.cif.'
_cod_database_code               7159744
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.687
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9134(12)
 0.0866(12)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C28(H28), C29(H29), C35(H35), C36(H36), C37(H37), C38(H38),
 C42(H42), C43(H43), C44(H44), C45(H45), C3(H3), C5(H5), C6(H6), C12(H12),
 C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22)
3.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              54199
_olex2_date_sample_completion    2022-07-27
_olex2_date_sample_data_collection 2022-07-27
_olex2_date_sample_submission    2022-07-27
_olex2_submission_original_sample_id ag108
_olex2_submission_special_instructions 'No special instructions were received'