Visible-light-triggered organophotoredox-catalyzed oxidation of 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles.
Ghosh, Sourav; Rana, Gopal; Kar, Abhishek; Sahoo, Rajkamal; Jana, Umasish; Organic & biomolecular chemistry 23 (2025) 5643–5656; doi:10.1039/d5ob00401b

data_7160538
_publ_section_title
;
 Visible-light-triggered organophotoredox-catalyzed oxidation of
 3-(benzylidine)indoline to indole-3-carbinols and 3-acyl indoles.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5643
_journal_page_last               5656
_journal_paper_doi               10.1039/d5ob00401b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C28 H24 N2 O3 S'
_chemical_formula_sum            'C28 H24 N2 O3 S'
_chemical_formula_weight         468.55
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-08-22 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                64.7130(10)
_cell_angle_beta                 76.619(2)
_cell_angle_gamma                82.311(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5972(5)
_cell_length_b                   11.4600(5)
_cell_length_c                   12.1476(6)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.60
_cell_volume                     1174.30(10)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34714
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.890
_exptl_absorpt_coefficient_mu    0.171
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0072P)^2^+1.4437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3933
_reflns_number_total             5289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00401b2.cif
_cod_data_source_block           uj_sg86a_0m
_cod_depositor_comments          'Adding full bibliography for 7160538.cif.'
_cod_database_code               7160538
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C), C00V(H00D,H00G,H00H)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              59743
_olex2_submission_special_instructions 'No special instructions were received'