Pyridine-oriented transannular C-H functionalization of arenes.
Hou, Yanchun; Liu, Jianwei; Tian, Yi; Wang, Guangshen; Zhang, Xingcan; Han, Jingpeng; Li, Baosheng; Chemical communications (Cambridge, England) 61 (2025) 1132–1135; doi:10.1039/d4cc05717a

data_7134038
_publ_section_title
;
 Pyridine-oriented transannular C-H functionalization of arenes.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1132
_journal_page_last               1135
_journal_paper_doi               10.1039/d4cc05717a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C25 H19 N'
_chemical_formula_sum            'C25 H19 N'
_chemical_formula_weight         333.41
_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     dual
_audit_creation_date             2024-08-28
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-08-29 deposited with the CCDC.	2024-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                100.211(4)
_cell_angle_beta                 100.569(4)
_cell_angle_gamma                109.946(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7811(4)
_cell_length_b                   9.7347(4)
_cell_length_c                   13.6565(7)
_cell_measurement_reflns_used    7954
_cell_measurement_temperature    302.34(10)
_cell_measurement_theta_max      76.0600
_cell_measurement_theta_min      5.2490
_cell_volume                     923.13(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.34(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_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     78.00 112.00   0.50    0.05    --  104.76-125.00 120.00   68
  2  \w     62.00  88.00   0.50    0.05    --   46.68-125.00 -30.00   52
  3  \w     35.00 101.00   0.50    0.05    --  104.76 -94.00 -60.00  132
  4  \w     78.00 112.00   0.50    0.05    --  104.76-125.00 -90.00   68
  5  \w     41.00 111.00   0.50    0.05    --  104.76-125.00-180.00  140
  6  \w     58.00  98.00   0.50    0.05    --  104.76 -94.00   0.00   80
  7  \w     64.00 105.00   0.50    0.05    --  104.76 -94.00 150.00   82
  8  \w     72.00 106.00   0.50    0.05    --  104.76 -77.00  30.00   68
  9  \w     32.00  68.00   0.50    0.05    --  104.76 -77.00  30.00   72
 10  \w     32.00  57.00   0.50    0.05    --  104.76 -61.00   0.00   50
 11  \w     12.00  38.00   0.50    0.05    --   46.68 -32.00-146.00   52
 12  \w     94.00 119.00   0.50    0.05    --  104.76  45.00-150.00   50
 13  \w    141.00 166.00   0.50    0.05    --  104.76  45.00-150.00   50
 14  \w     93.00 119.00   0.50    0.05    --  104.76  32.00  12.00   52
 15  \w    124.00 175.00   0.50    0.05    --  104.76  32.00  12.00  102
 16  \w     99.00 174.00   0.50    0.05    --  104.76  15.00 150.00  150
 17  \w     36.00 120.00   0.50    0.05    --   46.68  32.00  12.00  168
 18  \w    -24.00  29.00   0.50    0.05    --  -46.68  19.00 120.00  106
 19  \w    -67.00 -16.00   0.50    0.05    --  -46.68  77.00   0.00  102
 20  \w     -6.00  22.00   0.50    0.05    --  -46.68  77.00   0.00   56
 21  \w    -35.00   5.00   0.50    0.05    --  -46.68  32.00  12.00   80
 22  \w    -22.00  21.00   0.50    0.05    --  -46.68  37.00 150.00   86
 23  \w    -76.00 -50.00   0.50    0.05    -- -102.00 125.00  60.00   52
 24  \w   -108.00 -79.00   0.50    0.05    -- -102.00 125.00  60.00   58
 25  \w    -87.00 -59.00   0.50    0.05    -- -102.00 125.00 -90.00   56
 26  \w    -69.00 -41.00   0.50    0.05    -- -102.00 135.00-133.99   56
 27  \w   -119.00 -86.00   0.50    0.05    -- -102.00 135.00-133.99   66
 28  \w    -65.00 -30.00   0.50    0.05    -- -102.00  61.00   0.00   70
 29  \w    -56.00 -29.00   0.50    0.05    -- -102.00  77.00  60.00   54
 30  \w   -101.00 -63.00   0.50    0.05    -- -102.00  77.00  60.00   76
 31  \w    -58.00 -32.00   0.50    0.05    -- -102.00  61.00-120.00   52
 32  \w    -69.00 -31.00   0.50    0.05    -- -102.00  61.00-150.00   76
 33  \w   -102.00 -37.00   0.50    0.05    -- -102.00  77.00 -90.00  130
 34  \w   -168.00 -89.00   0.50    0.05    -- -102.00 -45.00  90.00  158
 35  \w   -124.00 -92.00   0.50    0.05    -- -102.00 -15.00 120.00   64
 36  \w   -148.00-106.00   0.50    0.05    -- -102.00 -30.00 -60.00   84
 37  \w   -114.00 -89.00   0.50    0.05    -- -102.00 -32.00-146.00   50
 38  \w   -174.00-130.00   0.50    0.05    -- -102.00 -32.00-146.00   88
 39  \w   -117.00 -38.00   0.50    0.05    --  -46.68 -32.00-146.00  158
 40  \w   -172.00-135.00   0.50    0.05    -- -102.00 -15.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1145538000
_diffrn_orient_matrix_UB_12      -0.1707370000
_diffrn_orient_matrix_UB_13      -0.0194610000
_diffrn_orient_matrix_UB_21      0.1829893000
_diffrn_orient_matrix_UB_22      -0.0215805000
_diffrn_orient_matrix_UB_23      0.0445582000
_diffrn_orient_matrix_UB_31      -0.0326772000
_diffrn_orient_matrix_UB_32      0.0278111000
_diffrn_orient_matrix_UB_33      0.1084240000
_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  0.0178
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10212
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.213
_diffrn_reflns_theta_min         3.409
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0545P)^2^+0.1134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3315
_reflns_number_total             3621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05717a2.cif
_cod_data_source_block           chenxiaoming_0828_auto
_cod_depositor_comments
'Adding full bibliography for 7134038--7134039.cif.'
_cod_original_cell_volume        923.13(8)
_cod_database_code               7134038
_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
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              86987
_shelx_hkl_checksum              74279
_shelx_fab_checksum              33501
_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.595