Green and sustainable dearomative cycloaddition of arenes via visible-light energy transfer catalysis: an atom-economical synthesis of N-heterocyclic skeletons
Gore, Babasaheb Sopan; Chen, Hsing-Yin; Wang, Jeh-Jeng; Green Chemistry 28 (2026) 2475–2484; doi:10.1039/D5GC04174K

data_7251695
_publ_section_title
;
 Green and sustainable dearomative cycloaddition of arenes via
 visible-light energy transfer catalysis: an atom-economical synthesis of
 N-heterocyclic skeletons
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2475
_journal_page_last               2484
_journal_paper_doi               10.1039/D5GC04174K
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C25 H20 N2 O2'
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_weight         380.43
_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             2022-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2025-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.878(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3481(3)
_cell_length_b                   11.4470(3)
_cell_length_c                   15.7580(4)
_cell_measurement_reflns_used    13635
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9510
_cell_measurement_theta_min      2.0020
_cell_volume                     1864.25(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -20.00 100.00   0.50   29.29    --   10.60  57.00  60.00  240
  2  \w    -79.00  36.00   0.50   29.29    --   10.60 -77.00 -60.00  230
  3  \w    -79.00  38.00   0.50   29.29    --   10.60 -82.00  60.00  234
  4  \w    -15.00 100.00   0.50   29.29    --   10.60  77.00  60.00  230
  5  \w    -79.00  38.00   0.50   29.29    --   10.60 -82.00-120.00  234
  6  \w    -79.00  36.00   0.50   29.29    --   10.60 -77.00 150.00  230
  7  \w    -15.00 100.00   0.50   29.29    --   10.60  77.00-120.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0193254000
_diffrn_orient_matrix_UB_12      0.0545429000
_diffrn_orient_matrix_UB_13      -0.0164484000
_diffrn_orient_matrix_UB_21      0.0317665000
_diffrn_orient_matrix_UB_22      0.0137261000
_diffrn_orient_matrix_UB_23      0.0396803000
_diffrn_orient_matrix_UB_31      0.0577933000
_diffrn_orient_matrix_UB_32      -0.0259185000
_diffrn_orient_matrix_UB_33      -0.0135419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0446
_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/[\s^2^(Fo^2^)+(0.0517P)^2^+0.5789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04174k2.cif
_cod_data_source_block           k11111-jjw-b(tpb-83)_auto
_cod_database_code               7251695
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_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:
 C11(H11), C3(H3), C10(H10), C9(H9), C8(H8), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C13(H13), C16(H16), C20(H20), C5(H5), C21(H21), C22(H22),
 C6(H6), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              50175
_shelx_hkl_checksum              37550
_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 2.870
_oxdiff_exptl_absorpt_empirical_full_min 0.605