Construction of benzimidazole- and indole-fused azabicyclo[3.1.0]hexanes bearing a cyano-containing quaternary center from vinylsulfonium salts through sequential [3 + 2]/[2 + 1] cyclization.
Li, Yuming; Gou, Yan; Hou, Shanling; Xu, Yanwei; Yang, Yuxing; Wan, Zhihan; Fan, Zhi; Organic & biomolecular chemistry 23 (2025) 1325–1329; doi:10.1039/d4ob01615g

data_7160287
_publ_section_title
;
 Construction of benzimidazole- and indole-fused azabicyclo[3.1.0]hexanes
 bearing a cyano-containing quaternary center from vinylsulfonium salts
 through sequential [3 + 2]/[2 + 1] cyclization.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1325
_journal_page_last               1329
_journal_paper_doi               10.1039/d4ob01615g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H17 N2 O S'
_chemical_formula_sum            'C24 H17 N2 O S'
_chemical_formula_weight         381.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8487(19)
_cell_length_b                   11.0122(12)
_cell_length_c                   8.5823(8)
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.985
_cell_measurement_theta_min      3.009
_cell_volume                     1875.9(3)
_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      293.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_min         2.115
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1668 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0861P)^2^+0.7867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2717
_reflns_number_total             3814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01615g2.cif
_cod_data_source_block           20240407
_cod_depositor_comments
'Adding full bibliography for 7160287--7160288.cif.'
_cod_database_code               7160287
_shelx_shelxl_version_number     2014/7
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5), C4(H4), C3(H3), C17(H17), C13(H13), C15(H15),
 C24(H24), C14(H14), C16(H16), C23(H23)
;
_shelx_res_checksum              19622
_olex2_submission_special_instructions 'No special instructions were received'