#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:25:57 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298024 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134038.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134038
loop_
_publ_author_name
'Hou, Yanchun'
'Liu, Jianwei'
'Tian, Yi'
'Wang, Guangshen'
'Zhang, Xingcan'
'Han, Jingpeng'
'Li, Baosheng'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 112.00   0.50    0.05    --  104.76-125.00 120.00   68
  2  ω     62.00  88.00   0.50    0.05    --   46.68-125.00 -30.00   52
  3  ω     35.00 101.00   0.50    0.05    --  104.76 -94.00 -60.00  132
  4  ω     78.00 112.00   0.50    0.05    --  104.76-125.00 -90.00   68
  5  ω     41.00 111.00   0.50    0.05    --  104.76-125.00-180.00  140
  6  ω     58.00  98.00   0.50    0.05    --  104.76 -94.00   0.00   80
  7  ω     64.00 105.00   0.50    0.05    --  104.76 -94.00 150.00   82
  8  ω     72.00 106.00   0.50    0.05    --  104.76 -77.00  30.00   68
  9  ω     32.00  68.00   0.50    0.05    --  104.76 -77.00  30.00   72
 10  ω     32.00  57.00   0.50    0.05    --  104.76 -61.00   0.00   50
 11  ω     12.00  38.00   0.50    0.05    --   46.68 -32.00-146.00   52
 12  ω     94.00 119.00   0.50    0.05    --  104.76  45.00-150.00   50
 13  ω    141.00 166.00   0.50    0.05    --  104.76  45.00-150.00   50
 14  ω     93.00 119.00   0.50    0.05    --  104.76  32.00  12.00   52
 15  ω    124.00 175.00   0.50    0.05    --  104.76  32.00  12.00  102
 16  ω     99.00 174.00   0.50    0.05    --  104.76  15.00 150.00  150
 17  ω     36.00 120.00   0.50    0.05    --   46.68  32.00  12.00  168
 18  ω    -24.00  29.00   0.50    0.05    --  -46.68  19.00 120.00  106
 19  ω    -67.00 -16.00   0.50    0.05    --  -46.68  77.00   0.00  102
 20  ω     -6.00  22.00   0.50    0.05    --  -46.68  77.00   0.00   56
 21  ω    -35.00   5.00   0.50    0.05    --  -46.68  32.00  12.00   80
 22  ω    -22.00  21.00   0.50    0.05    --  -46.68  37.00 150.00   86
 23  ω    -76.00 -50.00   0.50    0.05    -- -102.00 125.00  60.00   52
 24  ω   -108.00 -79.00   0.50    0.05    -- -102.00 125.00  60.00   58
 25  ω    -87.00 -59.00   0.50    0.05    -- -102.00 125.00 -90.00   56
 26  ω    -69.00 -41.00   0.50    0.05    -- -102.00 135.00-133.99   56
 27  ω   -119.00 -86.00   0.50    0.05    -- -102.00 135.00-133.99   66
 28  ω    -65.00 -30.00   0.50    0.05    -- -102.00  61.00   0.00   70
 29  ω    -56.00 -29.00   0.50    0.05    -- -102.00  77.00  60.00   54
 30  ω   -101.00 -63.00   0.50    0.05    -- -102.00  77.00  60.00   76
 31  ω    -58.00 -32.00   0.50    0.05    -- -102.00  61.00-120.00   52
 32  ω    -69.00 -31.00   0.50    0.05    -- -102.00  61.00-150.00   76
 33  ω   -102.00 -37.00   0.50    0.05    -- -102.00  77.00 -90.00  130
 34  ω   -168.00 -89.00   0.50    0.05    -- -102.00 -45.00  90.00  158
 35  ω   -124.00 -92.00   0.50    0.05    -- -102.00 -15.00 120.00   64
 36  ω   -148.00-106.00   0.50    0.05    -- -102.00 -30.00 -60.00   84
 37  ω   -114.00 -89.00   0.50    0.05    -- -102.00 -32.00-146.00   50
 38  ω   -174.00-130.00   0.50    0.05    -- -102.00 -32.00-146.00   88
 39  ω   -117.00 -38.00   0.50    0.05    --  -46.68 -32.00-146.00  158
 40  ω   -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       'ω 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/[σ²(Fo²)+(0.0545P)²+0.1134P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63158(14) 0.32575(13) 0.42991(8) 0.0584(3) Uani 1 1 d . . . . .
C1 C 0.61156(14) 0.66664(12) 0.25025(7) 0.0409(2) Uani 1 1 d . . . . .
C2 C 0.30736(18) 0.68869(17) 0.19901(10) 0.0618(3) Uani 1 1 d . . . . .
H2 H 0.236488 0.748678 0.199161 0.074 Uiso 1 1 calc R U . . .
C3 C 1.2054(2) 1.06254(14) 0.24483(13) 0.0707(4) Uani 1 1 d . . . . .
H3 H 1.308472 1.151545 0.280678 0.085 Uiso 1 1 calc R U . . .
C4 C 0.61968(14) 0.40134(11) 0.18420(7) 0.0404(2) Uani 1 1 d . . . . .
C5 C 0.22264(17) 0.53756(17) 0.14983(10) 0.0620(3) Uani 1 1 d . . . . .
H5 H 0.093570 0.493545 0.117276 0.074 Uiso 1 1 calc R U . . .
C6 C 0.52638(14) 0.51275(12) 0.19837(7) 0.0398(2) Uani 1 1 d . . . . .
C7 C 0.33131(15) 0.45175(14) 0.14928(9) 0.0516(3) Uani 1 1 d . . . . .
H7 H 0.273432 0.349418 0.115108 0.062 Uiso 1 1 calc R U . . .
C8 C 0.68920(14) 0.34544(12) 0.26395(8) 0.0426(2) Uani 1 1 d . . . . .
C9 C 1.08814(19) 0.98160(14) 0.29757(10) 0.0619(3) Uani 1 1 d . . . . .
H9 H 1.113448 1.017377 0.368626 0.074 Uiso 1 1 calc R U . . .
C10 C 0.61151(16) 0.33402(13) 0.08305(8) 0.0509(3) Uani 1 1 d . . . . .
H10 H 0.567540 0.370913 0.029550 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6540(2) 0.3892(2) 0.52915(10) 0.0695(4) Uani 1 1 d . . . . .
H11 H 0.596085 0.327410 0.568139 0.083 Uiso 1 1 calc R U . . .
C12 C 0.71346(14) 0.41695(12) 0.37410(8) 0.0434(2) Uani 1 1 d . . . . .
C13 C 1.01676(16) 0.88145(14) 0.08802(10) 0.0542(3) Uani 1 1 d . . . . .
H13 H 0.991457 0.847222 0.016842 0.065 Uiso 1 1 calc R U . . .
C14 C 0.81945(14) 0.75603(12) 0.30830(8) 0.0431(2) Uani 1 1 d . . . . .
H14 H 0.819968 0.829856 0.367467 0.052 Uiso 1 1 calc R U . . .
C15 C 1.17002(18) 1.01187(14) 0.14020(11) 0.0602(3) Uani 1 1 d . . . . .
H15 H 1.249308 1.065513 0.104865 0.072 Uiso 1 1 calc R U . . .
C16 C 0.93377(14) 0.84821(11) 0.24621(8) 0.0430(2) Uani 1 1 d . . . . .
C17 C 0.6670(2) 0.21442(15) 0.06077(10) 0.0624(3) Uani 1 1 d . . . . .
H17 H 0.661336 0.172096 -0.006967 0.075 Uiso 1 1 calc R U . . .
C18 C 0.92703(14) 0.66557(12) 0.35350(8) 0.0463(3) Uani 1 1 d . . . . .
H18A H 0.945964 0.600566 0.297470 0.056 Uiso 1 1 calc R U . . .
H18B H 1.050943 0.735486 0.396544 0.056 Uiso 1 1 calc R U . . .
C19 C 0.8454(2) 0.62995(16) 0.51994(9) 0.0614(3) Uani 1 1 d . . . . .
H19 H 0.918894 0.731840 0.550809 0.074 Uiso 1 1 calc R U . . .
C20 C 0.82568(15) 0.57009(13) 0.41643(8) 0.0451(2) Uani 1 1 d . . . . .
C21 C 0.7309(2) 0.15778(15) 0.13912(11) 0.0652(3) Uani 1 1 d . . . . .
H21 H 0.766877 0.076190 0.124459 0.078 Uiso 1 1 calc R U . . .
C22 C 0.49812(17) 0.75140(14) 0.24825(9) 0.0531(3) Uani 1 1 d . . . . .
H22 H 0.553650 0.854126 0.281459 0.064 Uiso 1 1 calc R U . . .
C23 C 0.7568(2) 0.5392(2) 0.57681(10) 0.0735(4) Uani 1 1 d . . . . .
H23 H 0.766328 0.578557 0.645715 0.088 Uiso 1 1 calc R U . . .
C24 C 0.89871(15) 0.79976(12) 0.14036(8) 0.0467(2) Uani 1 1 d . . . . .
H24 H 0.795033 0.711558 0.103813 0.056 Uiso 1 1 calc R U . . .
C25 C 0.74125(17) 0.22284(13) 0.23948(9) 0.0550(3) Uani 1 1 d . . . . .
H25 H 0.784006 0.183876 0.292042 0.066 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 117.27(12) . . ?
C6 C1 C14 127.08(9) . . ?
C22 C1 C6 117.95(10) . . ?
C22 C1 C14 114.95(10) . . ?
C5 C2 C22 119.67(11) . . ?
C15 C3 C9 120.23(12) . . ?
C8 C4 C6 123.79(9) . . ?
C10 C4 C6 117.30(9) . . ?
C10 C4 C8 118.25(10) . . ?
C2 C5 C7 119.03(11) . . ?
C1 C6 C4 127.85(9) . . ?
C1 C6 C7 118.18(10) . . ?
C7 C6 C4 113.93(9) . . ?
C5 C7 C6 122.57(12) . . ?
C4 C8 C12 121.49(9) . . ?
C25 C8 C4 119.11(10) . . ?
C25 C8 C12 119.37(9) . . ?
C3 C9 C16 121.17(12) . . ?
C17 C10 C4 121.64(11) . . ?
N1 C11 C23 124.09(12) . . ?
N1 C12 C8 117.00(10) . . ?
N1 C12 C20 122.85(10) . . ?
C20 C12 C8 120.05(9) . . ?
C15 C13 C24 120.67(11) . . ?
C1 C14 C18 116.28(9) . . ?
C16 C14 C1 113.21(8) . . ?
C16 C14 C18 108.93(8) . . ?
C3 C15 C13 119.40(11) . . ?
C9 C16 C14 119.29(10) . . ?
C24 C16 C9 117.81(10) . . ?
C24 C16 C14 122.75(9) . . ?
C21 C17 C10 119.82(11) . . ?
C20 C18 C14 113.22(8) . . ?
C23 C19 C20 120.21(13) . . ?
C12 C20 C18 121.25(9) . . ?
C19 C20 C12 117.47(11) . . ?
C19 C20 C18 121.25(11) . . ?
C17 C21 C25 119.58(11) . . ?
C2 C22 C1 122.58(12) . . ?
C11 C23 C19 118.03(12) . . ?
C16 C24 C13 120.70(10) . . ?
C21 C25 C8 121.57(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.3385(17) . ?
N1 C12 1.3443(14) . ?
C1 C6 1.3998(15) . ?
C1 C14 1.5255(14) . ?
C1 C22 1.3988(14) . ?
C2 C5 1.370(2) . ?
C2 C22 1.3777(18) . ?
C3 C9 1.3872(19) . ?
C3 C15 1.369(2) . ?
C4 C6 1.5017(14) . ?
C4 C8 1.4034(14) . ?
C4 C10 1.4001(14) . ?
C5 C7 1.3766(17) . ?
C6 C7 1.4059(14) . ?
C8 C12 1.4893(14) . ?
C8 C25 1.3921(15) . ?
C9 C16 1.3874(16) . ?
C10 C17 1.3786(17) . ?
C11 C23 1.368(2) . ?
C12 C20 1.3930(16) . ?
C13 C15 1.3698(18) . ?
C13 C24 1.3896(16) . ?
C14 C16 1.5222(14) . ?
C14 C18 1.5373(14) . ?
C16 C24 1.3828(15) . ?
C17 C21 1.377(2) . ?
C18 C20 1.5021(15) . ?
C19 C20 1.3887(15) . ?
C19 C23 1.372(2) . ?
C21 C25 1.3795(18) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 1.000 0.500 67.4 10.0 ?
