Annulation of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans.
Zhong, Zukang; Liao, Lihua; Liu, Yunyun; Zhang, Ming; Wan, Jie-Ping; Chemical communications (Cambridge, England) 59 (2023) 6885–6888; doi:10.1039/d3cc01687k

data_7131616
_publ_section_title
;
 Annulation of enaminones with quinonediimides/quinoneimides for selective
 synthesis of indoles and 2-aminobenzofurans.
;
_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6885
_journal_page_last               6888
_journal_paper_doi               10.1039/d3cc01687k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 N3 O6 S'
_chemical_formula_sum            'C24 H21 N3 O6 S'
_chemical_formula_weight         479.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-18 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.313(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8433(6)
_cell_length_b                   8.3762(5)
_cell_length_c                   25.2432(16)
_cell_measurement_reflns_used    5913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7530
_cell_measurement_theta_min      4.0780
_cell_volume                     2255.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_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    4.34    --   16.85  77.00-180.00   52
  2  \w      0.00  84.00   1.00    4.34    --   16.85  57.00 -60.00   84
  3  \w    -50.00  34.00   1.00    4.34    --   16.85 -57.00 -30.00   84
  4  \w    -55.00  46.00   1.00    4.34    --   16.85 -19.00-180.00  101
  5  \w    -89.00 -46.00   1.00    4.34    --  -15.92 178.00   0.00   43
;
_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      0.0336511000
_diffrn_orient_matrix_UB_12      0.0228475000
_diffrn_orient_matrix_UB_13      -0.0204368000
_diffrn_orient_matrix_UB_21      0.0558040000
_diffrn_orient_matrix_UB_22      0.0053602000
_diffrn_orient_matrix_UB_23      0.0194582000
_diffrn_orient_matrix_UB_31      0.0131423000
_diffrn_orient_matrix_UB_32      -0.0813586000
_diffrn_orient_matrix_UB_33      -0.0044487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16583
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0419P)^2^+1.3567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3884
_reflns_number_total             4605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01687k2.cif
_cod_data_source_block           zzk-dj_auto
_cod_depositor_comments          'Adding full bibliography for 7131616.cif.'
_cod_database_code               7131616
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              41725
_shelx_hkl_checksum              8445
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.706