Catalyst-controlled regio- and chemodivergent C–H functionalization of imidazopyridines with TIPS-protected terminal alkynes
Zhu, Tiantian; Zhang, Qiang; Li, Xianling; Liang, Taoyuan; Zhao, Shuangliang; Zhang, Zhuan; Chemical Communications  (2026) –; doi:10.1039/D6CC01180B

data_7135720
_publ_section_title
;
 Catalyst-controlled regio- and chemodivergent C-H functionalization of
 imidazopyridines with TIPS-protected terminal alkynes.
;
_journal_issue                   34
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8752
_journal_page_last               8755
_journal_paper_doi               10.1039/d6cc01180b
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C24 H29 F N2 Si'
_chemical_formula_sum            'C24 H29 F N2 Si'
_chemical_formula_weight         392.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-12-19
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-13 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.322(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7706(8)
_cell_length_b                   14.9937(10)
_cell_length_c                   12.2093(8)
_cell_measurement_reflns_used    2204
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.9340
_cell_measurement_theta_min      4.5100
_cell_volume                     2323.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.973
_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    -31.00  45.00   1.00    4.00    --   35.25 -57.00  60.00   76
  2  \w     22.00  82.00   1.00    4.00    --   35.25-125.00-150.00   60
  3  \w     -4.00  37.00   1.00    4.00    --   35.25 -77.00   0.00   41
  4  \w     20.00  99.00   1.00    4.00    --   35.25  57.00 -60.00   79
  5  \w     38.00  87.00   1.00    4.00    --   35.25-125.00  30.00   49
  6  \w     85.00 176.00   1.00    7.50    --  105.75  30.00 120.00   91
  7  \w     46.00  72.00   1.00    7.50    --  105.75 -77.00 -30.00   26
  8  \w     66.00 117.00   1.00    7.50    --  105.75 -61.00  30.00   51
  9  \w    105.00 168.00   1.00    7.50    --  105.75 111.00   0.00   63
 10  \w    120.00 162.00   1.00    7.50    --  105.75 111.00 -30.00   42
 11  \w     43.00 107.00   1.00    7.50    --  105.75-111.00   0.00   64
 12  \w     53.00 121.00   1.00    7.50    --  105.75 -61.00 -30.00   68
 13  \w     81.00 106.00   1.00    7.50    --  105.75 -77.00 -30.00   25
 14  \w     51.00 113.00   1.00    7.50    --  105.75 -30.00  60.00   62
;
_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      0.0043433000
_diffrn_orient_matrix_UB_12      0.0587047000
_diffrn_orient_matrix_UB_13      -0.1030275000
_diffrn_orient_matrix_UB_21      0.1162877000
_diffrn_orient_matrix_UB_22      0.0217023000
_diffrn_orient_matrix_UB_23      0.0376058000
_diffrn_orient_matrix_UB_31      0.0343986000
_diffrn_orient_matrix_UB_32      -0.0813930000
_diffrn_orient_matrix_UB_33      -0.0642004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8506
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.080
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
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    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0904P)^2^+0.6547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3194
_reflns_number_total             4379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01180b2.cif
_cod_data_source_block           exp_15047_auto
_cod_depositor_comments
'Adding full bibliography for 7135720--7135721.cif.'
_cod_database_code               7135720
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.886
_diffrn_oxdiff_ac3_digest_hkl    415ccf3abf2cfa4db6b8d73e7c5af77764e3a8
_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 Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C1(H1), C5(H5), C22(H22), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              81374
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.639