I2/DMSO-mediated substrate selective oxidation of tetrahydro indole-2,4-dione towards 4-hydroxy isatins and 5,6-dihydro-1H-indole-2,4-dione derivatives
Sinha, Goutam; Pramanik, Sayan; Jana, Debashis; Ghosh, Anirban; Mukhopadhyay, Chhanda; New Journal of Chemistry 48 (2024) 12544–12552; doi:10.1039/D4NJ01583E

data_7063265
_publ_section_title
;
 I2/DMSO-mediated substrate selective oxidation of tetrahydro
 indole-2,4-dione towards 4-hydroxy isatins and
 5,6-dihydro-1H-indole-2,4-dione derivatives
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12544
_journal_page_last               12552
_journal_paper_doi               10.1039/D4NJ01583E
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H12 Br N O3'
_chemical_formula_sum            'C20 H12 Br N O3'
_chemical_formula_weight         394.227
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2023-06-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.65(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.47(3)
_cell_length_b                   15.27(2)
_cell_length_c                   6.904(10)
_cell_measurement_reflns_used    4321
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      25.139
_cell_measurement_theta_min      2.533
_cell_volume                     1706(5)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9926
_diffrn_measured_fraction_theta_max 0.9804
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.9926
_diffrn_reflns_Laue_measured_fraction_max 0.9804
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19041
_diffrn_reflns_point_group_measured_fraction_full 0.9926
_diffrn_reflns_point_group_measured_fraction_max 0.9804
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.27
_diffrn_reflns_theta_min         2.52
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1723 before and 0.0905 after correction.
The Ratio of minimum to maximum transmission is 0.4040.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             791.684
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.9564
_refine_diff_density_min         -0.9213
_refine_diff_density_rms         0.1290
_refine_ls_d_res_high            0.7756
_refine_ls_d_res_low             8.0920
_refine_ls_goodness_of_fit_ref   1.0367
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0367
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1268P)^2^+0.1153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2357
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2081
_reflns_number_total             3751
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4nj01583e2.cif
_cod_data_source_block           mo_AB190623_0m_a
_cod_depositor_comments
'Adding full bibliography for 7063265--7063267.cif.'
_cod_original_cell_volume        1706(4)
_cod_database_code               7063265
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P)
2.b Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_olex2_submission_special_instructions 'No special instructions were received'