<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_1576661
_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         'C26 H23 N3 O2'
_chemical_formula_sum            'C26 H23 N3 O2'
_chemical_formula_weight         409.47
_chemical_name_systematic        5?-Me
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-25
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0386(5)
_cell_length_b                   14.8556(6)
_cell_length_c                   18.6742(6)
_cell_measurement_reflns_used    8528
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.9170
_cell_measurement_theta_min      2.2230
_cell_volume                     4172.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.832
_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    -69.00 -38.00   0.50   10.00    --    3.32 -42.00 130.00   62
  2  \w      1.00  33.00   0.50   10.00    --    3.32 -99.00  30.00   64
  3  \w    -73.00 -41.00   0.50   10.00    --    3.32 -37.00  30.00   64
  4  \w    -31.00   4.00   0.50   10.00    --    3.32 -37.00  30.00   70
  5  \w    -29.00  18.00   0.50   10.00    --    3.32 -42.00 130.00   94
;
_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      0.0339445000
_diffrn_orient_matrix_UB_12      0.0243001000
_diffrn_orient_matrix_UB_13      -0.0179898000
_diffrn_orient_matrix_UB_21      0.0211697000
_diffrn_orient_matrix_UB_22      -0.0410661000
_diffrn_orient_matrix_UB_23      -0.0091946000
_diffrn_orient_matrix_UB_31      -0.0249864000
_diffrn_orient_matrix_UB_32      -0.0017951000
_diffrn_orient_matrix_UB_33      -0.0321587000
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.815
_diffrn_reflns_theta_min         2.181
_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    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53326
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc/pentane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.002
_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^+1.8445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4111
_reflns_number_total             4984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09309k2.cif
_cod_data_source_block           knm323a-gpc2-fr1_etoac_pentane_x-ray_auto
_cod_database_code               1576661
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N O H'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.983
_diffrn_oxdiff_digest_frames
;
0186bf8ded6acc556ed0e7cf9a551bf4830002538d4
;
_diffrn_oxdiff_digest_hkl
;
0188151e5c02857470486bbb57c2190e8237cf
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C2(H009), C1(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H00F), C8(H00G), C31(H00H), C27(H00I), C4(H00J), C28(H00K), C3(H00L),
 C6(H00M), C7(H00N), C24(H00O), C21(H00P), C29(H00Q), C30(H00R), C22(H00T),
 C23(H00U)
2.c Idealised Me refined as rotating group:
 C16(H00A,H00B,H00C), C18(H00E,H00S,H00V)
;
_shelx_res_checksum              59870
_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 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.514