Visible-light driven acetoxylation and dioxygenation of indoles <i>via</i> electron donor-acceptor complexes.
Paul, Aditya; Sengupta, Arunava; Yadav, Somnath; Chemical communications (Cambridge, England) 59 (2023) 7455–7458; doi:10.1039/d3cc01683h

data_7131693
_publ_section_title
;
 Visible-light driven acetoxylation and dioxygenation of indoles
 <i>via</i> electron donor-acceptor complexes.
;
_journal_issue                   48
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7455
_journal_page_last               7458
_journal_paper_doi               10.1039/d3cc01683h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_melting_point          413.0
_chemical_name_common            Isatin
_chemical_name_systematic        3J
_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             2023-04-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-03 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5072(8)
_cell_length_b                   23.008(3)
_cell_length_c                   7.4733(6)
_cell_measurement_reflns_used    1217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0680
_cell_measurement_theta_min      3.5370
_cell_volume                     1290.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -10.00  42.00   1.00   32.50    --   13.76  77.00  90.00   52
  2  \w    -82.00 -19.00   1.00   32.50    --  -15.95 -57.00   0.00   63
  3  \w    -29.00  -3.00   1.00   32.50    --  -15.95 -57.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513890000
_diffrn_orient_matrix_UB_12      0.0207508000
_diffrn_orient_matrix_UB_13      0.0249770000
_diffrn_orient_matrix_UB_21      -0.0791611000
_diffrn_orient_matrix_UB_22      -0.0137151000
_diffrn_orient_matrix_UB_23      -0.0161792000
_diffrn_orient_matrix_UB_31      0.0002802000
_diffrn_orient_matrix_UB_32      -0.0916717000
_diffrn_orient_matrix_UB_33      0.0080851000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3374
_diffrn_reflns_point_group_measured_fraction_full 0.768
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.991
_exptl_transmission_factor_min   0.975
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0308P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.420
_reflns_Friedel_fraction_full    0.496
_reflns_Friedel_fraction_max     0.495
_reflns_number_gt                1259
_reflns_number_total             1746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01683h4.cif
_cod_data_source_block           3J
_cod_depositor_comments
'Adding full bibliography for 7131693--7131694.cif.'
_cod_database_code               7131693
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C68 H52 O8 N1 '
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.512
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C16(H16), C12(H12), C13(H13), C5(H5), C15(H15), C14(H14)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              47199
_shelx_hkl_checksum              29647
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.705