Gold-catalyzed ligand-controlled annulation for the construction of indoles and furoindoles
Jia, Xiaoni; Kan, Yuanmeng; Li, Wenguang; Kong, Weiguang; Gao, Wenchao; Chen, Ming; Ye, Long-Wu; Li, Ting; Chemical Communications 61 (2025) 9294–9297; doi:10.1039/D5CC02328A

data_7134567
_publ_section_title
;
 Gold-catalyzed ligand-controlled annulation for the construction of
 indoles and furoindoles
;
_journal_issue                   51
_journal_name_full               'Chemical Communications'
_journal_page_first              9294
_journal_page_last               9297
_journal_paper_doi               10.1039/D5CC02328A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C24 H19 N O4 S'
_chemical_formula_sum            'C24 H19 N O4 S'
_chemical_formula_weight         417.46
_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     iterative
_audit_creation_date             2024-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-04-08 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                69.355(5)
_cell_angle_beta                 80.379(5)
_cell_angle_gamma                85.929(6)
_cell_formula_units_Z            2
_cell_length_a                   8.5808(7)
_cell_length_b                   9.8636(6)
_cell_length_c                   12.7357(6)
_cell_measurement_reflns_used    1958
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7890
_cell_measurement_theta_min      3.7520
_cell_volume                     994.43(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -60.00   73
  2  \w    -71.00  39.00   1.00    1.00    --  -33.50  19.00-180.00  110
  3  \w   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  \w   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00   0.00   87
  5  \w    -32.00  55.00   1.00    1.00    --   36.53 -57.00 150.00   87
  6  \w    -14.00  46.00   1.00    1.00    --   36.53 -57.00-150.00   60
  7  \w     34.00  65.00   1.00    1.00    --   36.53 -77.00-150.00   31
  8  \w    -34.00  -6.00   1.00    1.00    --   36.53 -37.00-120.00   28
  9  \w     78.00 111.00   1.00    1.00    --   36.53 178.00 -90.00   33
 10  \w    -16.00  30.00   1.00    1.00    --   36.53 -77.00-180.00   46
 11  \w     28.00  55.00   1.00    1.00    --   36.53 -77.00  60.00   27
 12  \w     64.00 110.00   1.00    1.00    --   36.53 178.00  60.00   46
 13  \w    -15.00  11.00   1.00    1.00    --   36.53 -77.00-150.00   26
 14  \w     10.00  36.00   1.00    1.00    --   36.53 -99.00  60.00   26
 15  \w     38.00  76.00   1.00    1.00    --   36.53 -99.00  60.00   38
 16  \w     76.00 111.00   1.00    1.00    --   36.53 178.00  30.00   35
 17  \w     61.00 106.00   1.00    6.00    --  108.00 -94.00-120.00   45
 18  \w     49.00 134.00   1.00    6.00    --  108.00 -30.00-180.00   85
 19  \w     43.00  76.00   1.00    6.00    --  108.00 -61.00-180.00   33
 20  \w     60.00 109.00   1.00    6.00    --  108.00-111.00  60.00   49
 21  \w    113.00 158.00   1.00    6.00    --  108.00  77.00 -60.00   45
 22  \w     40.00 109.00   1.00    6.00    --  108.00-111.00 150.00   69
 23  \w     38.00 106.00   1.00    6.00    --  108.00 -94.00-180.00   68
 24  \w     39.00  90.00   1.00    6.00    --  108.00 -94.00 -30.00   51
 25  \w    136.00 175.00   1.00    6.00    --  108.00  45.00-120.00   39
 26  \w     89.00 115.00   1.00    6.00    --  108.00  45.00-120.00   26
 27  \w     38.00 122.00   1.00    6.00    --  108.00 -45.00 -30.00   84
 28  \w     62.00 130.00   1.00    6.00    --  108.00 -77.00-120.00   68
 29  \w    131.00 175.00   1.00    6.00    --  108.00  61.00 -30.00   44
 30  \w    123.00 167.00   1.00    6.00    --  108.00  77.00 -90.00   44
 31  \w     36.00 145.00   1.00    6.00    --  108.00 -15.00 -90.00  109
 32  \w     39.00  72.00   1.00    6.00    --  108.00 -94.00  90.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1187284000
_diffrn_orient_matrix_UB_12      0.1100153000
_diffrn_orient_matrix_UB_13      0.0000620000
_diffrn_orient_matrix_UB_21      -0.1239317000
_diffrn_orient_matrix_UB_22      0.0525854000
_diffrn_orient_matrix_UB_23      0.0801219000
_diffrn_orient_matrix_UB_31      0.0609070000
_diffrn_orient_matrix_UB_32      -0.1139884000
_diffrn_orient_matrix_UB_33      0.1033751000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7017
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.753
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0565
_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/[\s^2^(Fo^2^)+(0.0817P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1670
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2428
_reflns_number_total             3527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02328a2.cif
_cod_data_source_block           202409321_auto
_cod_depositor_comments
'Adding full bibliography for 7134566--7134567.cif.'
_cod_database_code               7134567
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31O6N3S1
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.759
_reflns_odcompleteness_completeness 99.35
_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 C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O4) = Uanis(O4A)
Uanis(C24) = Uanis(C24A)
3. Others
 Sof(O4A)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(O4)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              76297
_shelx_hkl_checksum              59746
_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 1.640
_oxdiff_exptl_absorpt_empirical_full_min 0.793