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_7134039
_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         'C23 H17 N'
_chemical_formula_sum            'C23 H17 N'
_chemical_formula_weight         307.38
_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             2023-08-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2024-08-29 deposited with the CCDC.	2024-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.70210(10)
_cell_length_b                   7.22330(10)
_cell_length_c                   23.9872(3)
_cell_measurement_reflns_used    9244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5240
_cell_measurement_theta_min      3.6990
_cell_volume                     1675.25(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -54.00  -2.00   1.00    1.00    --    0.00 -77.00 -60.00   52
  2  \w      3.00  30.00   1.00    1.00    --    0.00 -77.00 -60.00   27
  3  \w     18.00  63.00   1.00    1.00    --    0.00  57.00  60.00   45
  4  \w    -18.00   7.00   1.00    1.00    --    0.00  57.00  60.00   25
  5  \w    -12.00  13.00   1.00    1.00    --   54.00 -57.00  90.00   25
  6  \w     16.00 123.00   1.00    1.00    --   54.00  19.00-120.00  107
  7  \w    -11.00  66.00   1.00    1.00    --   54.00 -77.00  60.00   77
  8  \w    -13.00  72.00   1.00    1.00    --   54.00 -57.00 -60.00   85
  9  \w    -18.00  62.00   1.00    1.00    --   54.00 -38.00 150.00   80
 10  \w     23.00  99.00   1.00    1.00    --   54.00-125.00 -60.00   76
 11  \w     25.00  69.00   1.00    1.00    --   54.00 -57.00  90.00   44
 12  \w     38.00  67.00   1.00    1.00    --  108.00-111.00 150.00   29
 13  \w    106.00 147.00   1.00    1.00    --  108.00 178.00-120.00   41
 14  \w     85.00 111.00   1.00    1.00    --  108.00-111.00 150.00   26
 15  \w     57.00  83.00   1.00    1.00    --  108.00 178.00-120.00   26
 16  \w    123.00 149.00   1.00    1.00    --  108.00  50.00 150.00   26
 17  \w     58.00 115.00   1.00    1.00    --  108.00 178.00  90.00   57
 18  \w     84.00 112.00   1.00    1.00    --  108.00-111.00-150.00   28
 19  \w     70.00 105.00   1.00    1.00    --  108.00 -50.00 150.00   35
 20  \w     79.00 113.00   1.00    1.00    --  108.00-111.00   0.00   34
 21  \w     37.00  63.00   1.00    1.00    --  108.00-111.00   0.00   26
 22  \w     87.00 116.00   1.00    1.00    --  108.00  50.00 150.00   29
 23  \w     99.00 129.00   1.00    1.00    --  108.00 -63.00 -60.00   30
 24  \w     63.00  89.00   1.00    1.00    --  108.00 -77.00-180.00   26
 25  \w     93.00 124.00   1.00    1.00    --  108.00 -77.00-180.00   31
 26  \w    123.00 173.00   1.00    1.00    --  108.00  63.00-120.00   50
 27  \w     41.00  81.00   1.00    1.00    --  108.00 -38.00-180.00   40
 28  \w     87.00 177.00   1.00    1.00    --  108.00  50.00  60.00   90
 29  \w     42.00  84.00   1.00    1.00    --  108.00-111.00 120.00   42
 30  \w    101.00 126.00   1.00    1.00    --  108.00 -63.00   0.00   25
 31  \w     79.00 108.00   1.00    1.00    --  108.00  77.00 -30.00   29
 32  \w     71.00  96.00   1.00    1.00    --  108.00-111.00  60.00   25
 33  \w    101.00 151.00   1.00    1.00    --  108.00 111.00   0.00   50
 34  \w     40.00 129.00   1.00    1.00    --  108.00 -63.00 -90.00   89
 35  \w    151.00 176.00   1.00    1.00    --  108.00  63.00  90.00   25
 36  \w    117.00 177.00   1.00    1.00    --  108.00  77.00 -30.00   60
 37  \w     75.00 100.00   1.00    1.00    --  108.00-111.00  30.00   25
 38  \w     90.00 118.00   1.00    1.00    --  108.00  63.00-120.00   28
 39  \w     87.00 124.00   1.00    1.00    --  108.00  63.00  90.00   37
 40  \w     81.00 107.00   1.00    1.00    --  108.00-109.00 -73.00   26
 41  \w     36.00  62.00   1.00    1.00    --  108.00 -17.00  83.00   26
 42  \w     91.00 173.00   1.00    1.00    --  108.00  50.00 120.00   82
 43  \w    103.00 146.00   1.00    1.00    --  108.00 111.00-180.00   43
 44  \w     76.00 112.00   1.00    1.00    --  108.00-111.00  90.00   36
 45  \w    115.00 140.00   1.00    1.00    --  108.00 111.00  30.00   25
 46  \w    129.00 155.00   1.00    1.00    --  108.00 111.00 150.00   26
 47  \w     40.00  79.00   1.00    1.00    --  108.00-111.00-150.00   39
 48  \w     97.00 123.00   1.00    1.00    --  108.00 -63.00 -30.00   26
 49  \w     98.00 139.00   1.00    1.00    --  108.00 178.00   0.00   41
 50  \w     66.00 100.00   1.00    1.00    --  108.00 178.00  30.00   34
 51  \w     59.00  85.00   1.00    1.00    --  108.00 -25.00-120.00   26
 52  \w    114.00 140.00   1.00    1.00    --  108.00  38.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0639129000
_diffrn_orient_matrix_UB_12      0.1875373000
_diffrn_orient_matrix_UB_13      -0.0143485000
_diffrn_orient_matrix_UB_21      0.1443405000
_diffrn_orient_matrix_UB_22      -0.0900616000
_diffrn_orient_matrix_UB_23      0.0028143000
_diffrn_orient_matrix_UB_31      -0.0217803000
_diffrn_orient_matrix_UB_32      -0.0469192000
_diffrn_orient_matrix_UB_33      -0.0627643000
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15651
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.624
_diffrn_reflns_theta_min         3.698
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0075(4)
_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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.2462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             3207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05717a2.cif
_cod_data_source_block           20230804-ljw-1
_cod_depositor_comments
'Adding full bibliography for 7134038--7134039.cif.'
_cod_database_code               7134039
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H17 N'
_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:
 C004(H004)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H),
 C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N),
 C00N(H00O), C00O(H00P)
;
_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 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.837