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_1575615
_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         'C23 H17 N O2'
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-20
_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                90
_cell_angle_beta                 90.856(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4543(2)
_cell_length_b                   9.7225(4)
_cell_length_c                   28.3302(9)
_cell_measurement_reflns_used    3039
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      73.5740
_cell_measurement_theta_min      4.7920
_cell_volume                     1777.58(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -29.00  -4.00   1.00    1.00    --   40.73 -57.00 150.00   25
  2  \w     37.00  66.00   1.00    2.41    --  106.95 -61.00  30.00   29
  3  \w     85.00 114.00   1.00    2.41    --  106.95 -61.00  30.00   29
  4  \w     66.00 104.00   1.00    2.41    --  106.95 -61.00-120.00   38
  5  \w     78.00 152.00   1.00    2.41    --  106.95  61.00  30.00   74
  6  \w    122.00 169.00   1.00    2.41    --  106.95  61.00  90.00   47
  7  \w     98.00 169.00   1.00    2.41    --  106.95 125.00  30.00   71
  8  \w     93.00 173.00   1.00    2.41    --  106.95  45.00 150.00   80
  9  \w     78.00 118.00   1.00    2.41    --  106.95  61.00  90.00   40
 10  \w    105.00 130.00   1.00    2.41    --  106.95 125.00-180.00   25
 11  \w    -77.00  -8.00   1.00    1.00    --  -40.73 125.00   0.00   69
 12  \w   -115.00  -8.00   1.00    1.00    --  -40.73 -77.00 -60.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0903355000
_diffrn_orient_matrix_UB_12      0.0457259000
_diffrn_orient_matrix_UB_13      0.0475051000
_diffrn_orient_matrix_UB_21      -0.1439809000
_diffrn_orient_matrix_UB_22      0.1021197000
_diffrn_orient_matrix_UB_23      -0.0261091000
_diffrn_orient_matrix_UB_31      -0.1677079000
_diffrn_orient_matrix_UB_32      -0.1121459000
_diffrn_orient_matrix_UB_33      -0.0043557000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6527
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.683
_diffrn_reflns_theta_min         3.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0079(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0981P)^2^+0.8112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2921
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04380h2.cif
_cod_data_source_block           c-24-3
_cod_depositor_comments
'Adding full bibliography for 1575614--1575615.cif.'
_cod_database_code               1575615
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.910
_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. Restrained distances
 C16-C15
 1.45 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), 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)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              65822
_shelx_hkl_checksum              2630
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.640
_oxdiff_exptl_absorpt_empirical_full_min 0.690