<i>L</i>-region-selective annulative π-extension through dearomative activation of polycyclic aromatic hydrocarbons.
Nakata, Kanami; Matsuoka, Wataru; Ito, Hideto; Itami, Kenichiro; Chemical science 17 (2026) 3998–4003; doi:10.1039/d5sc09309k

data_1576664
_publ_section_title
;
 <i>L</i>-region-selective annulative &#x3c0;-extension through
 dearomative activation of polycyclic aromatic hydrocarbons.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              3998
_journal_page_last               4003
_journal_paper_doi               10.1039/d5sc09309k
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C17 H10'
_chemical_formula_sum            'C17 H10'
_chemical_formula_weight         214.25
_chemical_name_systematic        'tribenzo[a,c,j]picene (compound 11)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-27
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_audit_update_record
;
2025-11-27 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.831(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.780(3)
_cell_length_b                   3.8860(4)
_cell_length_c                   19.6341(18)
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.2690
_cell_measurement_theta_min      2.3430
_cell_volume                     1992.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.823
_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    -15.00  32.00   0.50   25.00    --   -2.54  57.00-180.00   94
  2  \w    -20.00   6.00   0.50   25.00    --   -2.54 -19.00 120.00   52
  3  \w    -51.00   8.00   0.50   25.00    --   -2.54 -57.00 -60.00  118
  4  \w    -11.00  35.00   0.50   25.00    --    3.16 -99.00 -60.00   92
  5  \w    -11.00  38.00   0.50   25.00    --    3.16 -99.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_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      -0.0145604000
_diffrn_orient_matrix_UB_12      0.1540411000
_diffrn_orient_matrix_UB_13      -0.0046194000
_diffrn_orient_matrix_UB_21      0.0228715000
_diffrn_orient_matrix_UB_22      0.0975977000
_diffrn_orient_matrix_UB_23      0.0097437000
_diffrn_orient_matrix_UB_31      0.0018847000
_diffrn_orient_matrix_UB_32      0.0067767000
_diffrn_orient_matrix_UB_33      -0.0354425000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.128
_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 (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CS2/pentane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0772P)^2^+0.8857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1797
_reflns_number_total             2311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09309k2.cif
_cod_data_source_block           knm441a_gpc2-fr2_cs2-pentane_x-ray_auto
_cod_database_code               1576664
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.980
_diffrn_oxdiff_digest_frames
;
01a52dc06e079a15d2989cafe9ff799b6f00025a2ee
;
_diffrn_oxdiff_digest_hkl        01c6962592cc8a956093c4f6494a226581a990
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H002), C2(H008), C5(H00A), C13(H00B), C6(H00C), C14(H00D), C12(H00E),
 C11(H00F), C8(H00G), C7(H00H)
;
_shelx_res_checksum              48616
_olex2_exptl_crystal_mounting_method loop
_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 2.613
_oxdiff_exptl_absorpt_empirical_full_min 0.622