Sulfenylnitrene-mediated aminative cyclizations for the diastereoselective synthesis of fused bicyclic indolines.
Herndon, Deacon; Kafle, Prakash; Mukherjee, Rishav; Sharma, Indrajeet; RSC advances 16 (2026) 16370–16375; doi:10.1039/d5ra09687a

data_7251852
_publ_section_title
;
 Sulfenylnitrene-mediated aminative cyclizations for the
 diastereoselective synthesis of fused bicyclic indolines.
;
_journal_issue                   18
_journal_name_full               'RSC advances'
_journal_page_first              16370
_journal_page_last               16375
_journal_paper_doi               10.1039/d5ra09687a
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C23 H22 N4 O4 S2'
_chemical_formula_sum            'C23 H22 N4 O4 S2'
_chemical_formula_weight         482.56
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-08-05
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-10 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5245(9)
_cell_length_b                   8.0424(3)
_cell_length_c                   12.9761(5)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.71
_cell_volume                     2229.43(15)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'PHOTON II'
_diffrn_detector_area_resol_mean '7.41 pixels/mm'
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44956
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         2.706
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_power             '50 W'
_diffrn_source_type              'Incoatec I\mS 2.0 High Brilliance'
_diffrn_source_voltage           '50.0 kV'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1542 before and 0.1042 after correction.
The Ratio of minimum to maximum transmission is 0.5847.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method
'Vapor diffusion of hexane into dichloromethane solution.'
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0465P)^2^+1.9118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4099
_reflns_number_total             4350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra09687a2.cif
_cod_data_source_block           25077
_cod_database_code               7251852
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.851
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C20(H20), C12(H12), C5(H5), C9(H9), C19(H19), C21(H21),
 C22(H22), C4(H4A), C6(H6), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              44993
_olex2_date_sample_data_collection 2025-07-28
_olex2_date_sample_submission    2025-07-28
_olex2_exptl_crystal_mounting_method
'Crystal mounted on a MiTeGen MicroMount using paratone oil.'
_olex2_submission_original_sample_id PK_DH_05_76
_olex2_submission_special_instructions 'No special instructions were received'