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_7131694
_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         'C17 H14 Br N O2'
_chemical_formula_sum            'C17 H14 Br N O2'
_chemical_formula_weight         344.20
_chemical_melting_point          448.0
_chemical_name_common            3-acetoxy-indole
_chemical_name_systematic        2K
_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
_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
;
2023-05-11 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.767(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6226(8)
_cell_length_b                   17.3895(10)
_cell_length_c                   9.3029(7)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7950
_cell_measurement_theta_min      2.9130
_cell_volume                     1490.5(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 1.000
_diffrn_measured_fraction_theta_max 0.845
_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  29.00   1.00   37.50    --   13.76 -57.00 -30.00   39
  2  \w    -78.00   6.00   1.00   37.50    --  -15.95   0.00-120.00   84
  3  \w     11.00  53.00   1.00   37.50    --  -15.95   0.00-120.00   42
  4  \w    -40.00   7.00   1.00   37.50    --  -15.95 -77.00  60.00   47
;
_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      0.0011594000
_diffrn_orient_matrix_UB_12      0.0378162000
_diffrn_orient_matrix_UB_13      -0.0282707000
_diffrn_orient_matrix_UB_21      0.0668275000
_diffrn_orient_matrix_UB_22      0.0071047000
_diffrn_orient_matrix_UB_23      0.0553592000
_diffrn_orient_matrix_UB_31      0.0381729000
_diffrn_orient_matrix_UB_32      -0.0135538000
_diffrn_orient_matrix_UB_33      -0.0497681000
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.407
_diffrn_reflns_theta_min         2.210
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37177
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   0.680
_exptl_transmission_factor_min   0.613
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0413P)^2^+0.4537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2543
_reflns_number_total             3479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01683h4.cif
_cod_data_source_block           2K
_cod_depositor_comments
'Adding full bibliography for 7131693--7131694.cif.'
_cod_database_code               7131694
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C68 H56 Br4 N8 O4 '
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.372
_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), C7(H7), C2(H2), C15(H15), C6(H6), C11(H11), C13(H13), C14(H14),
 C12(H12)
1.c Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C)
;
_shelx_res_checksum              19312
_shelx_hkl_checksum              56013
_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.610