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_7159745
_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         'C28 H22 N2 O3.965 S0.983'
_chemical_formula_sum            'C28 H22 N2 O3.97 S0.98'
_chemical_formula_weight         481.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.045(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3157(15)
_cell_length_b                   17.700(3)
_cell_length_c                   12.6167(18)
_cell_measurement_reflns_used    6062
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.25
_cell_volume                     2358.4(6)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            58637
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.928
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1499 before and 0.0817 after correction.
The Ratio of minimum to maximum transmission is 0.7421.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             1006
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0573P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2284
_reflns_number_total             4390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01613g2.cif
_cod_data_source_block           ag112
_cod_depositor_comments
'Adding full bibliography for 7159744--7159745.cif.'
_cod_database_code               7159745
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(O3)=Sof(S1)=Sof(O2)=1-FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C24(H24), C25(H25), C11(H11), C15(H15), C26(H26), C12(H12),
 C18(H18), C4(H4), C14(H14), C13(H13), C22(H22), C20(H20), C19(H19), C6(H6),
 C5(H5), C21(H21), C7(H7)
;
_shelx_res_checksum              17299
_olex2_date_sample_completion    2022-12-12
_olex2_date_sample_data_collection 2022-12-12
_olex2_date_sample_submission    2022-12-20
_olex2_submission_original_sample_id AG_112
_olex2_submission_special_instructions 'No special instructions were received'