#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:09:19 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131693.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131693
loop_
_publ_author_name
'Paul, Aditya'
'Sengupta, Arunava'
'Yadav, Somnath'
_publ_section_title
;
 Visible-light driven acetoxylation and dioxygenation of indoles
 via 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  42.00   1.00   32.50    --   13.76  77.00  90.00   52
  2  ω    -82.00 -19.00   1.00   32.50    --  -15.95 -57.00   0.00   63
  3  ω    -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       'ω 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/[σ²(Fo²)+(0.0308P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3435(4) 0.21669(11) 0.2073(3) 0.0758(8) Uani 1 1 d . . . . .
O1 O 0.3011(3) 0.34326(10) 0.1728(3) 0.0782(8) Uani 1 1 d . . . . .
N1 N 0.4402(3) 0.34229(11) 0.4480(3) 0.0503(7) Uani 1 1 d . . . . .
C8 C 0.5045(4) 0.29851(13) 0.5676(4) 0.0428(8) Uani 1 1 d . . . . .
C9 C 0.4750(4) 0.24367(13) 0.4917(4) 0.0446(8) Uani 1 1 d . . . . .
C11 C 0.5895(4) 0.43902(13) 0.4331(4) 0.0459(8) Uani 1 1 d . . . . .
C7 C 0.5845(4) 0.30390(15) 0.7346(4) 0.0484(8) Uani 1 1 d . . . . .
C4 C 0.5194(4) 0.19240(14) 0.5805(5) 0.0543(9) Uani 1 1 d . . . . .
H4 H 0.499271 0.156236 0.528778 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3924(4) 0.25141(15) 0.3184(4) 0.0528(9) Uani 1 1 d . . . . .
C1 C 0.4248(4) 0.40462(13) 0.4796(4) 0.0579(9) Uani 1 1 d . . . . .
H1A H 0.397044 0.410899 0.604855 0.069 Uiso 1 1 calc R U . . .
H1B H 0.325752 0.419439 0.409768 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6264(4) 0.25157(17) 0.8202(4) 0.0564(9) Uani 1 1 d . . . . .
H6 H 0.679114 0.253440 0.932604 0.068 Uiso 1 1 calc R U . . .
C2 C 0.3698(5) 0.31821(16) 0.2970(5) 0.0566(9) Uani 1 1 d . . . . .
C16 C 0.7218(5) 0.41696(13) 0.3260(4) 0.0568(9) Uani 1 1 d . . . . .
H16 H 0.711992 0.379118 0.283333 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6077(5) 0.49571(14) 0.4948(5) 0.0626(10) Uani 1 1 d . . . . .
H12 H 0.519877 0.511550 0.567788 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7530(6) 0.52857(16) 0.4496(6) 0.0748(12) Uani 1 1 d . . . . .
H13 H 0.762760 0.566436 0.491940 0.090 Uiso 1 1 calc R U . . .
C5 C 0.5943(4) 0.19749(17) 0.7483(4) 0.0599(10) Uani 1 1 d . . . . .
H5 H 0.623324 0.164294 0.813093 0.072 Uiso 1 1 calc R U . . .
C10 C 0.6301(5) 0.36022(15) 0.8266(5) 0.0703(11) Uani 1 1 d . . . . .
H10A H 0.682204 0.386523 0.741744 0.105 Uiso 1 1 calc R U . . .
H10B H 0.713447 0.352869 0.921419 0.105 Uiso 1 1 calc R U . . .
H10C H 0.523803 0.377154 0.875356 0.105 Uiso 1 1 calc R U . . .
C15 C 0.8693(5) 0.44973(17) 0.2801(5) 0.0735(12) Uani 1 1 d . . . . .
H15 H 0.957912 0.433968 0.207848 0.088 Uiso 1 1 calc R U . . .
C14 C 0.8841(6) 0.50603(18) 0.3423(6) 0.0800(12) Uani 1 1 d . . . . .
H14 H 0.982401 0.528537 0.311608 0.096 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 128.2(3) . . ?
C2 N1 C8 111.2(3) . . ?
C2 N1 C1 120.2(3) . . ?
C9 C8 N1 109.1(3) . . ?
C7 C8 N1 130.1(3) . . ?
C7 C8 C9 120.8(3) . . ?
C8 C9 C3 108.6(3) . . ?
C4 C9 C8 122.1(3) . . ?
C4 C9 C3 129.3(3) . . ?
C16 C11 C1 122.2(3) . . ?
C16 C11 C12 118.0(3) . . ?
C12 C11 C1 119.8(3) . . ?
C8 C7 C6 115.5(3) . . ?
C8 C7 C10 125.8(3) . . ?
C6 C7 C10 118.7(3) . . ?
C9 C4 H4 121.4 . . ?
C5 C4 C9 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
O2 C3 C9 131.6(3) . . ?
O2 C3 C2 123.3(3) . . ?
C9 C3 C2 105.1(3) . . ?
N1 C1 C11 114.4(3) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C11 C1 H1A 108.7 . . ?
C11 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C7 C6 H6 117.9 . . ?
C5 C6 C7 124.1(3) . . ?
C5 C6 H6 117.9 . . ?
O1 C2 N1 127.4(3) . . ?
O1 C2 C3 126.7(3) . . ?
N1 C2 C3 105.9(3) . . ?
C11 C16 H16 119.3 . . ?
C11 C16 C15 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.209(4) . ?
O1 C2 1.208(4) . ?
N1 C8 1.431(4) . ?
N1 C1 1.458(3) . ?
N1 C2 1.364(4) . ?
C8 C9 1.401(4) . ?
C8 C7 1.391(4) . ?
C9 C4 1.394(4) . ?
C9 C3 1.447(4) . ?
C11 C1 1.509(4) . ?
C11 C16 1.373(4) . ?
C11 C12 1.390(4) . ?
C7 C6 1.399(4) . ?
C7 C10 1.506(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C3 C2 1.555(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.383(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.381(5) . ?
C14 H14 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C2 O1 1.0(6) . . . . ?
O2 C3 C2 N1 180.0(3) . . . . ?
N1 C8 C9 C4 -178.1(3) . . . . ?
N1 C8 C9 C3 0.8(3) . . . . ?
N1 C8 C7 C6 177.8(3) . . . . ?
N1 C8 C7 C10 -3.0(5) . . . . ?
C8 N1 C1 C11 88.5(3) . . . . ?
C8 N1 C2 O1 178.1(3) . . . . ?
C8 N1 C2 C3 -0.8(3) . . . . ?
C8 C9 C4 C5 0.1(4) . . . . ?
C8 C9 C3 O2 -179.8(4) . . . . ?
C8 C9 C3 C2 -1.3(3) . . . . ?
C8 C7 C6 C5 0.5(5) . . . . ?
C9 C8 C7 C6 -1.9(4) . . . . ?
C9 C8 C7 C10 177.3(3) . . . . ?
C9 C4 C5 C6 -1.5(5) . . . . ?
C9 C3 C2 O1 -177.7(3) . . . . ?
C9 C3 C2 N1 1.3(3) . . . . ?
C11 C16 C15 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C7 C8 C9 C4 1.7(4) . . . . ?
C7 C8 C9 C3 -179.4(3) . . . . ?
C7 C6 C5 C4 1.2(5) . . . . ?
C4 C9 C3 O2 -1.0(6) . . . . ?
C4 C9 C3 C2 177.5(3) . . . . ?
C3 C9 C4 C5 -178.6(3) . . . . ?
C1 N1 C8 C9 172.4(3) . . . . ?
C1 N1 C8 C7 -7.3(5) . . . . ?
C1 N1 C2 O1 5.1(5) . . . . ?
C1 N1 C2 C3 -173.9(3) . . . . ?
C1 C11 C16 C15 177.9(3) . . . . ?
C1 C11 C12 C13 -177.8(3) . . . . ?
C2 N1 C8 C9 0.0(3) . . . . ?
C2 N1 C8 C7 -179.7(3) . . . . ?
C2 N1 C1 C11 -99.7(3) . . . . ?
C16 C11 C1 N1 17.1(4) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
C16 C15 C14 C13 0.4(6) . . . . ?
C12 C11 C1 N1 -165.0(3) . . . . ?
C12 C11 C16 C15 0.0(5) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C10 C7 C6 C5 -178.8(3) . . . . ?
