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_7134566
_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_absolute_configuration rm
_chemical_formula_moiety         'C24 H18 Br N O4 S'
_chemical_formula_sum            'C24 H18 Br N O4 S'
_chemical_formula_weight         496.36
_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     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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4774(3)
_cell_length_b                   19.8681(3)
_cell_length_c                   5.66262(13)
_cell_measurement_reflns_used    4454
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7160
_cell_measurement_theta_min      4.4390
_cell_volume                     2191.31(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  30.00   87
  2  \w    -44.00  34.00   1.00    1.00    --  -33.50  57.00  90.00   78
  3  \w    -47.00  36.00   1.00    1.00    --  -33.50  37.00-180.00   83
  4  \w    -18.00  11.00   1.00    1.00    --   36.47 -77.00  90.00   29
  5  \w     64.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   46
  6  \w     32.00  73.00   1.00    1.00    --   36.47 -99.00 -90.00   41
  7  \w     47.00 108.00   1.00    1.00    --   36.47  19.00  30.00   61
  8  \w     72.00 104.00   1.00    1.00    --   36.47 178.00 150.00   32
  9  \w     35.00  64.00   1.00    1.00    --   36.47 -77.00  90.00   29
 10  \w     61.00  86.00   1.00    1.00    --   36.47 178.00 -90.00   25
 11  \w    127.00 162.00   1.00    3.50    --  108.00  45.00-120.00   35
 12  \w    122.00 154.00   1.00    3.50    --  108.00 111.00 120.00   32
 13  \w     38.00 128.00   1.00    3.50    --  108.00 -45.00 120.00   90
 14  \w     39.00 123.00   1.00    3.50    --  108.00 -45.00 -30.00   84
 15  \w    120.00 177.00   1.00    3.50    --  108.00  77.00  60.00   57
 16  \w     57.00 108.00   1.00    3.50    --  108.00-111.00 150.00   51
 17  \w     75.00 101.00   1.00    3.50    --  108.00 -94.00 -90.00   26
 18  \w     83.00 172.00   1.00    3.50    --  108.00  30.00 150.00   89
 19  \w    -73.00 -47.00   1.00    1.00    --  -33.50 -57.00  90.00   26
 20  \w     61.00  86.00   1.00    1.00    --   36.47 178.00 120.00   25
 21  \w    133.00 159.00   1.00    3.50    --  108.00  61.00 -60.00   26
 22  \w     89.00 115.00   1.00    3.50    --  108.00  61.00 -60.00   26
 23  \w     12.00  37.00   1.00    1.00    --  -33.50  37.00   0.00   25
;
_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      0.0745739000
_diffrn_orient_matrix_UB_12      0.0171338000
_diffrn_orient_matrix_UB_13      0.0679862000
_diffrn_orient_matrix_UB_21      0.0132769000
_diffrn_orient_matrix_UB_22      -0.0745960000
_diffrn_orient_matrix_UB_23      0.0586396000
_diffrn_orient_matrix_UB_31      0.0227589000
_diffrn_orient_matrix_UB_32      -0.0125076000
_diffrn_orient_matrix_UB_33      -0.2567759000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9493
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.777
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.451
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71090
_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    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 707 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0704P)^2^+0.3212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.399
_reflns_Friedel_fraction_full    0.498
_reflns_Friedel_fraction_max     0.498
_reflns_number_gt                2759
_reflns_number_total             3040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02328a2.cif
_cod_data_source_block           202409120_auto
_cod_depositor_comments
'Adding full bibliography for 7134566--7134567.cif.'
_cod_database_code               7134566
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H31O6N3S1
_shelx_estimated_absorpt_t_max   0.708
_shelx_estimated_absorpt_t_min   0.571
_reflns_odcompleteness_completeness 99.87
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              49430
_shelx_hkl_checksum              27901
_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.823