Facile access to 2-hydroxy-2-substituted indole-3-ones <i>via</i> a copper-catalyzed oxidative cyclization of 2-arylethynylanilines.
Sun, Weiqiang; Cui, Xueli; Qu, Jing; Cai, Xiaojia; Hu, Jinhui; Xiong, Zhuang; Guo, Suqin; Xu, Jun; Chen, Wen-Hua; Wu, Jia-Qiang; Chemical communications (Cambridge, England) 59 (2023) 7228–7231; doi:10.1039/d3cc01390a

data_7131640
_publ_section_title
;
 Facile access to 2-hydroxy-2-substituted indole-3-ones <i>via</i> a
 copper-catalyzed oxidative cyclization of 2-arylethynylanilines.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7228
_journal_page_last               7231
_journal_paper_doi               10.1039/d3cc01390a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'Br C15 N O3, 0.5[CH3COOCH2CH3]'
_chemical_formula_sum            'C17 H14 Br N O4'
_chemical_formula_weight         376.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-01-24 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.314(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.4178(4)
_cell_length_b                   5.70910(10)
_cell_length_c                   26.1253(4)
_cell_measurement_reflns_used    8415
_cell_measurement_temperature    298.19(10)
_cell_measurement_theta_max      76.1970
_cell_measurement_theta_min      3.6380
_cell_volume                     3369.24(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.19(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_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      9.00  48.00   0.50    0.08    --   46.95 -71.00 -75.00   78
  2  \w     37.00  88.00   0.50    0.33    --  108.74 -71.00 -75.00  102
  3  \w     45.00  70.00   0.50    0.33    --  108.74 -61.00 -30.00   50
  4  \w     40.00  70.00   0.50    0.33    --  108.74 -61.00-120.00   60
  5  \w     68.00 105.00   0.50    0.33    --  108.74 -77.00-180.00   74
  6  \w     63.00  92.00   0.50    0.33    --  108.74 -95.00-150.00   58
  7  \w     52.00 100.00   0.50    0.33    --  108.74-125.00-180.00   96
  8  \w    109.00 163.00   0.50    0.33    --  108.74  30.00 -30.00  108
  9  \w     93.00 162.00   0.50    0.33    --  108.74  45.00   0.00  138
 10  \w     97.00 177.00   0.50    0.33    --  108.74  77.00   0.00  160
 11  \w     86.00 169.00   0.50    0.33    --  108.74  71.00  55.00  166
 12  \w     48.00  73.00   0.50    0.08    --   46.95  71.00  55.00   50
 13  \w     40.00  66.00   0.50    0.33    --  108.74 -61.00 120.00   52
 14  \w    -69.00  26.00   0.50    0.08    --  -46.95  71.00  55.00  190
 15  \w    -51.00 -22.00   0.50    0.33    --  -88.50  45.00 -90.00   58
 16  \w    -50.00 -16.00   0.50    0.33    --  -88.50  45.00-120.00   68
 17  \w    -81.00 -44.00   0.50    0.33    --  -88.50  77.00  30.00   74
 18  \w    -75.00 -19.00   0.50    0.33    --  -88.50  71.00  55.00  112
 19  \w   -108.00 -25.00   0.50    0.08    --  -46.95 -71.00 -75.00  166
 20  \w   -100.00 -74.00   0.50    0.08    --  -46.95-125.00-180.00   52
 21  \w   -151.00-125.00   0.50    0.33    --  -88.50 -71.00 -75.00   52
 22  \w   -119.00 -85.00   0.50    0.08    --  -46.95-125.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0334519000
_diffrn_orient_matrix_UB_12      -0.2117616000
_diffrn_orient_matrix_UB_13      -0.0342238000
_diffrn_orient_matrix_UB_21      -0.0500609000
_diffrn_orient_matrix_UB_22      0.0372324000
_diffrn_orient_matrix_UB_23      0.0214290000
_diffrn_orient_matrix_UB_31      -0.0320451000
_diffrn_orient_matrix_UB_32      0.1631028000
_diffrn_orient_matrix_UB_33      -0.0493208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10924
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.270
_diffrn_reflns_theta_min         3.658
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0694P)^2^+4.3720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3131
_reflns_number_total             3350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01390a2.cif
_cod_data_source_block           exp_794
_cod_depositor_comments
'Adding full bibliography for 7131639--7131640.cif.'
_cod_database_code               7131640
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_shelx_estimated_absorpt_t_max   0.551
_shelx_estimated_absorpt_t_min   0.485
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 180 electrons were 
found in a volume of 972\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CH3COOCH2CH3] per Asymmetric Unit 
which account for 192 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              45320
_shelx_hkl_checksum              23585
_shelx_fab_checksum              84278
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.748