Self-induced charge transfer activation enables metal-free C-H coupling of polycyclic aromatic hydrocarbons under photo irradiation.
Kurokawa, Kazuma; Kohyama, Aki; Kuroda, Yusuke; Tao-Kakuyama, Keisuke; Takikawa, Hiroshi; Takasu, Kiyosei; Chemical science 17 (2026) 4942–4947; doi:10.1039/d5sc09144f

data_1576439
_publ_section_title
;
 Self-induced charge transfer activation enables metal-free C-H coupling
 of polycyclic aromatic hydrocarbons under photo irradiation.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              4942
_journal_page_last               4947
_journal_paper_doi               10.1039/d5sc09144f
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C30 H26 O2'
_chemical_formula_sum            'C30 H26 O2'
_chemical_formula_weight         418.51
_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     iterative
_audit_creation_date             2024-11-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-10-27 deposited with the CCDC.	2026-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                75.757(4)
_cell_angle_beta                 79.327(4)
_cell_angle_gamma                76.421(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6823(4)
_cell_length_b                   10.0325(5)
_cell_length_c                   14.5626(6)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    93
_cell_measurement_theta_max      72.1720
_cell_measurement_theta_min      3.1340
_cell_volume                     1047.75(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.906
_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    -84.00 -38.00   0.50    0.50    --    5.00  60.00  60.00   92
  2  \w    -84.00  94.00   0.50    0.50    --    5.00   0.00   0.00  356
  3  \w     14.00  43.00   0.50    0.50    --  -46.70  46.00  87.26   58
  4  \w   -136.00 -37.00   0.50    0.50    --  -46.70  60.00 150.00  198
  5  \w   -136.00 -25.00   0.50    0.50    --  -46.70  50.00  90.00  222
  6  \w   -187.00 -26.00   0.50    0.50    --  -97.40  50.00  30.00  322
  7  \w   -187.00 -37.00   0.50    0.50    --  -97.40  59.00 168.61  300
  8  \w   -187.00  -9.00   0.50    0.50    --  -97.40  45.00  -8.64  356
  9  \w   -187.00  -8.00   0.50    0.50    --  -97.40  10.00   0.00  358
 10  \w   -187.00 -37.00   0.50    0.50    --  -97.40  59.00  -1.18  300
 11  \w   -187.00 -38.00   0.50    0.50    --  -97.40  60.00 147.05  298
 12  \w   -187.00 -38.00   0.50    0.50    --  -97.40  60.00  89.34  298
 13  \w   -187.00 -38.00   0.50    0.50    --  -97.40  60.00  69.90  298
 14  \w   -187.00  -9.00   0.50    0.50    --  -97.40  45.00   7.29  356
 15  \w   -187.00  -8.00   0.50    0.50    --  -97.40  10.00 150.00  358
 16  \w   -187.00-118.00   0.50    0.50    --  -97.40  57.00  -6.26  138
 17  \w   -154.00 -79.00   0.50    0.50    --  -97.40  60.00 178.10  150
 18  \w   -164.00-138.00   0.50    0.50    --  -97.40  60.00   1.89   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1823008000
_diffrn_orient_matrix_UB_12      -0.0231160000
_diffrn_orient_matrix_UB_13      0.0597015000
_diffrn_orient_matrix_UB_21      0.0233133000
_diffrn_orient_matrix_UB_22      0.0893868000
_diffrn_orient_matrix_UB_23      0.0674004000
_diffrn_orient_matrix_UB_31      -0.0978545000
_diffrn_orient_matrix_UB_32      0.1326888000
_diffrn_orient_matrix_UB_33      -0.0634616000
_diffrn_radiation_collimation    0.3
_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  0.0491
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13654
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.189
_diffrn_reflns_theta_min         3.160
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0058(11)
_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     295
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.2492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3488
_reflns_number_total             3974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09144f2.cif
_cod_data_source_block           230526kk2_auto
_cod_depositor_comments
'Adding full bibliography for 1576439--1576445.cif.'
_cod_database_code               1576439
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 97.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C14(H14), C11(H11), C23(H23), C18(H18), C22(H22), C6(H6),
 C7(H7), C20(H20), C8(H8)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              32420
_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 2.729
_oxdiff_exptl_absorpt_empirical_full_min 0.629