Ir(III)-catalyzed selective C-H acylmethylation and dicarbonylation of indolizines with β-ketosulfoxonium ylides.
Yang, Zi-Feng; Meng, Yuan-Jie; Liu, Xin-Xing; Wei, Jiaohang; Wu, Wen-Rong; Liu, Xiang; Zhang, Shang-Shi; Feng, Pengju; Chemical communications (Cambridge, England) 61 (2025) 15441–15444; doi:10.1039/d5cc04380h

data_1575614
_publ_section_title
;
 Ir(III)-catalyzed selective C-H acylmethylation and dicarbonylation of
 indolizines with &#x3b2;-ketosulfoxonium ylides.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15441
_journal_page_last               15444
_journal_paper_doi               10.1039/d5cc04380h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C24 H21 N O'
_chemical_formula_sum            'C24 H21 N O'
_chemical_formula_weight         339.42
_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     direct
_audit_creation_date             2025-04-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-07-07 deposited with the CCDC.	2025-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.9658(12)
_cell_angle_beta                 102.0139(15)
_cell_angle_gamma                111.3771(18)
_cell_formula_units_Z            2
_cell_length_a                   8.96038(18)
_cell_length_b                   9.96982(17)
_cell_length_c                   11.70333(14)
_cell_measurement_reflns_used    7770
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5500
_cell_measurement_theta_min      5.0930
_cell_volume                     885.86(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.936
_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    112.00 137.00   0.50    0.05    --  106.94 119.00 172.00   50
  2  \w     19.00  64.00   0.50    0.05    --   43.18 -77.00 -90.00   90
  3  \w    -34.00  20.00   0.50    0.05    --   43.18 -38.00-150.00  108
  4  \w    -34.00  16.00   0.50    0.05    --   43.18 -38.00 -60.00  100
  5  \w    -27.00  21.00   0.50    0.05    --   43.18 -38.00 -30.00   96
  6  \w     -5.00  22.00   0.50    0.05    --   43.18 -38.00   0.00   54
  7  \w    -16.00  22.00   0.50    0.05    --   43.18 -38.00  60.00   76
  8  \w     48.00  90.00   0.50    0.05    --   43.18-126.00   0.00   84
  9  \w     54.00  80.00   0.50    0.05    --   43.18-119.00  88.00   52
 10  \w     13.00  50.00   0.50    0.05    --   43.18-119.00  88.00   74
 11  \w     38.00  74.00   0.50    0.05    --  106.94 -77.00  60.00   72
 12  \w     44.00  78.00   0.50    0.05    --  106.94 -77.00  30.00   68
 13  \w     96.00 138.00   0.50    0.05    --  106.94  15.00 -90.00   84
 14  \w     96.00 136.00   0.50    0.05    --  106.94  15.00-150.00   80
 15  \w    100.00 130.00   0.50    0.05    --  106.94  15.00 -60.00   60
 16  \w     92.00 117.00   0.50    0.05    --  106.94  15.00   0.00   50
 17  \w     94.00 152.00   0.50    0.05    --  106.94  45.00  90.00  116
 18  \w     67.00  93.00   0.50    0.05    --  106.94-119.00  88.00   52
 19  \w     59.00  85.00   0.50    0.05    --  106.94 -95.00 150.00   52
 20  \w     32.00  86.00   0.50    0.05    --  106.94 -95.00-180.00  108
 21  \w     37.00  92.00   0.50    0.05    --  106.94 -95.00 -60.00  110
 22  \w    -61.00 -30.00   0.50    0.05    -- -103.00 126.00 -30.00   62
 23  \w   -101.00 -66.00   0.50    0.05    -- -103.00 126.00   0.00   70
 24  \w   -101.00 -75.00   0.50    0.05    -- -103.00 126.00 -30.00   52
 25  \w    -97.00 -31.00   0.50    0.05    -- -103.00 115.00-158.24  132
 26  \w    -95.00 -69.00   0.50    0.05    -- -103.00 116.00  94.88   52
 27  \w    -56.00 -31.00   0.50    0.05    -- -103.00 116.00  94.88   50
 28  \w    -98.00 -72.00   0.50    0.05    -- -103.00 119.00 172.00   52
 29  \w    -72.00  -7.00   0.50    0.05    --  -43.18 119.00 172.00  130
 30  \w    -60.00 -34.00   0.50    0.05    -- -103.00 104.00 -22.24   52
 31  \w    -93.00 -64.00   0.50    0.05    -- -103.00 104.00 -22.24   58
 32  \w    -93.00 -37.00   0.50    0.05    -- -103.00 104.00 -98.25  112
 33  \w    -93.00 -56.00   0.50    0.05    -- -103.00 102.00-115.96   74
 34  \w    -92.00 -34.00   0.50    0.05    -- -103.00  97.00 118.67  116
 35  \w    -69.00 -44.00   0.50    0.05    -- -103.00  77.00 120.00   50
 36  \w     -9.00  25.00   0.50    0.05    --  -43.18  38.00 150.00   68
 37  \w    -70.00 -38.00   0.50    0.05    -- -103.00  77.00   0.00   64
 38  \w     -4.00  28.00   0.50    0.05    --  -43.18  38.00-120.00   64
 39  \w    -70.00 -32.00   0.50    0.05    -- -103.00  77.00 -30.00   76
 40  \w   -129.00 -88.00   0.50    0.05    -- -103.00 -15.00 -30.00   82
 41  \w   -128.00 -95.00   0.50    0.05    -- -103.00 -15.00 -90.00   66
 42  \w   -174.00-136.00   0.50    0.05    -- -103.00 -45.00 -90.00   76
 43  \w   -174.00 -99.00   0.50    0.05    -- -103.00 -77.00   0.00  150
 44  \w   -117.00 -89.00   0.50    0.05    -- -103.00 -15.00  60.00   56
 45  \w   -133.00 -93.00   0.50    0.05    -- -103.00 -15.00 120.00   80
 46  \w   -151.00 -91.00   0.50    0.05    -- -103.00-119.00  88.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319046000
_diffrn_orient_matrix_UB_12      -0.1180424000
_diffrn_orient_matrix_UB_13      -0.0934410000
_diffrn_orient_matrix_UB_21      0.0848543000
_diffrn_orient_matrix_UB_22      -0.0366477000
_diffrn_orient_matrix_UB_23      0.1088217000
_diffrn_orient_matrix_UB_31      -0.1738096000
_diffrn_orient_matrix_UB_32      -0.1286087000
_diffrn_orient_matrix_UB_33      -0.0188493000
_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  0.0114
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9136
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.826
_diffrn_reflns_theta_min         5.121
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0447P)^2^+0.3582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3340
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04380h2.cif
_cod_data_source_block           yzf-d-18
_cod_depositor_comments
'Adding full bibliography for 1575614--1575615.cif.'
_cod_database_code               1575614
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              40499
_shelx_hkl_checksum              39247
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.675