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_7131639
_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         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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
;
2023-01-23 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.215(2)
_cell_angle_beta                 96.665(2)
_cell_angle_gamma                106.787(2)
_cell_formula_units_Z            4
_cell_length_a                   7.90540(10)
_cell_length_b                   13.1683(3)
_cell_length_c                   19.1538(4)
_cell_measurement_reflns_used    10294
_cell_measurement_temperature    296.89(18)
_cell_measurement_theta_max      77.3780
_cell_measurement_theta_min      4.2670
_cell_volume                     1894.59(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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      296.89(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_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   -112.00 -38.00   0.50    2.11    --  -48.38 -35.00 -45.00  148
  2  \w     37.00 104.00   0.50    2.11    --   48.38  35.00 111.00  134
  3  \w     -9.00  40.00   0.50    2.11    --   48.38 -35.00 -45.00   98
  4  \w   -164.00 -87.00   0.50    8.45    --  -91.75 -35.00 -45.00  154
  5  \w    139.00 173.00   0.50    8.45    --  109.06  35.00 111.00   68
  6  \w     98.00 124.00   0.50    8.45    --  109.06  35.00 111.00   52
  7  \w    -10.00  27.00   0.50    2.11    --  -48.38  19.00-120.00   74
  8  \w    -39.00   0.00   0.50    2.11    --  -48.38  35.00 111.00   78
  9  \w    -19.00   8.00   0.50    2.11    --  -48.38  19.00-150.00   54
 10  \w    -61.00  13.00   0.50    2.11    --  -48.38  57.00 150.00  148
 11  \w   -101.00 -75.00   0.50    2.11    --  -48.38-125.00 -90.00   52
 12  \w    -13.00  42.00   0.50    2.11    --   48.38 -38.00-180.00  110
 13  \w    -85.00 -23.00   0.50    8.45    --  -91.75 125.00 -30.00  124
 14  \w   -120.00 -87.00   0.50    8.45    --  -91.75-125.00 150.00   66
 15  \w   -162.00-132.00   0.50    8.45    --  -91.75-125.00 150.00   60
 16  \w   -165.00 -80.00   0.50    8.45    --  -91.75 -19.00-180.00  170
 17  \w   -163.00 -79.00   0.50    8.45    --  -91.75 -57.00 120.00  168
 18  \w    -81.00 -28.00   0.50    8.45    --  -91.75  77.00  60.00  106
 19  \w    -62.00 -23.00   0.50    8.45    --  -91.75 125.00-180.00   78
 20  \w   -145.00 -81.00   0.50    8.45    --  -91.75 -57.00  90.00  128
 21  \w    -69.00 -28.00   0.50    8.45    --  -91.75 125.00-150.00   82
 22  \w     98.00 123.00   0.50    8.45    --  109.06  19.00-180.00   50
 23  \w     39.00  83.00   0.50    8.45    --  109.06 -99.00-150.00   88
 24  \w     37.00  65.00   0.50    8.45    --  109.06 -57.00  90.00   56
 25  \w     38.00  73.00   0.50    8.45    --  109.06 -77.00 -60.00   70
 26  \w     86.00 111.00   0.50    8.45    --  109.06-125.00  30.00   50
 27  \w    103.00 170.00   0.50    8.45    --  109.06  19.00  30.00  134
 28  \w     37.00 100.00   0.50    8.45    --  109.06 -99.00  60.00  126
 29  \w     40.00  73.00   0.50    8.45    --  109.06-125.00  30.00   66
 30  \w     56.00  94.00   0.50    8.45    --  109.06 -99.00 150.00   76
 31  \w     84.00 112.00   0.50    8.45    --  109.06-125.00 -30.00   56
 32  \w     49.00  75.00   0.50    8.45    --  109.06-125.00 -30.00   52
 33  \w     77.00 112.00   0.50    8.45    --  109.06-125.00-150.00   70
 34  \w     87.00 112.00   0.50    8.45    --  109.06-125.00 120.00   50
 35  \w     36.00  78.00   0.50    8.45    --  109.06 -99.00 -60.00   84
 36  \w    149.00 175.00   0.50    8.45    --  109.06  19.00-180.00   52
 37  \w     38.00  74.00   0.50    8.45    --  109.06-125.00-150.00   72
 38  \w     79.00 112.00   0.50    8.45    --  109.06-125.00   0.00   66
 39  \w     55.00 112.00   0.50    8.45    --  109.06-125.00 -90.00  114
 40  \w     43.00 105.00   0.50    8.45    --  109.06 -99.00  90.00  124
 41  \w     38.00  63.00   0.50    8.45    --  109.06 -57.00 120.00   50
;
_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      0.1922482000
_diffrn_orient_matrix_UB_12      0.0076217000
_diffrn_orient_matrix_UB_13      0.0309332000
_diffrn_orient_matrix_UB_21      -0.0615710000
_diffrn_orient_matrix_UB_22      -0.1164090000
_diffrn_orient_matrix_UB_23      0.0213199000
_diffrn_orient_matrix_UB_31      0.0362163000
_diffrn_orient_matrix_UB_32      -0.0366887000
_diffrn_orient_matrix_UB_33      -0.0718064000
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24273
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.638
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7566
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0774P)^2^+0.4090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6152
_reflns_number_total             7566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01390a2.cif
_cod_data_source_block           exp_1881_auto
_cod_depositor_comments
'Adding full bibliography for 7131639--7131640.cif.'
_cod_database_code               7131639
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.861
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C18(H18), C19(H19), C21(H21), C22(H22), N2(H2), C26(H26), C27(H27),
 C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C41(H41), C42(H42),
  C44(H44), C45(H45)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              37912
_shelx_hkl_checksum              96733
_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.764