Visible-light-induced regioselective chalcogenation of indoloquinoxalines <i>via</i> cross-dehydrogenative coupling under metal-free, open-air conditions.
Bera, Biman; Dutta, Rahul; Ghorai, Shubhankar; Ganguly, Jhuma; Bera, Mrinal K.; Organic & biomolecular chemistry 23 (2025) 8695–8703; doi:10.1039/d5ob01088h

data_7160707
_publ_section_title
;
 Visible-light-induced regioselective chalcogenation of indoloquinoxalines
 <i>via</i> cross-dehydrogenative coupling under metal-free, open-air
 conditions.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8695
_journal_page_last               8703
_journal_paper_doi               10.1039/d5ob01088h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C25 H16 N2 S2'
_chemical_formula_weight         408.52
_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
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2025-05-07 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.458(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6925(19)
_cell_length_b                   15.819(2)
_cell_length_c                   10.5522(16)
_cell_measurement_reflns_used    45337
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.895
_cell_measurement_theta_min      1.735
_cell_volume                     1958.0(5)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            44247
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        23.511
_diffrn_reflns_theta_max         23.511
_diffrn_reflns_theta_min         1.736
_exptl_absorpt_coefficient_mu    0.286
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
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_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1122
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_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^)+(0.1126P)^2^+7.0915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2232
_refine_ls_wR_factor_ref         0.2479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2248
_reflns_number_total             2887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01088h2.cif
_cod_data_source_block           MKB_INDOLE_QUINO_THIO18_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7160707.cif.'
_cod_original_cell_volume        1958.1(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160707
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              7867