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_7251694
_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         'C26 H22 N2 O'
_chemical_formula_sum            'C26 H22 N2 O'
_chemical_formula_weight         378.45
_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             2022-07-27
_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                 93.655(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3638(3)
_cell_length_b                   11.3229(3)
_cell_length_c                   16.6651(5)
_cell_measurement_reflns_used    12610
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8590
_cell_measurement_theta_min      1.9660
_cell_volume                     1951.64(10)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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    -17.00 100.00   0.50   15.49    --   10.60  82.00 -60.00  234
  2  \w    -79.00  41.00   0.50   15.49    --   10.60 -57.00  30.00  240
  3  \w    -15.00 100.00   0.50   15.49    --   10.60  77.00 -30.00  230
  4  \w   -100.00  17.00   0.50   15.49    --  -10.90 -82.00  90.00  234
  5  \w    -36.00  79.00   0.50   15.49    --  -10.90  77.00-150.00  230
  6  \w    -36.00  79.00   0.50   15.49    --  -10.90  77.00 -90.00  230
  7  \w    -79.00  36.00   0.50   15.49    --   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      0.0088742000
_diffrn_orient_matrix_UB_12      0.0136355000
_diffrn_orient_matrix_UB_13      -0.0408409000
_diffrn_orient_matrix_UB_21      -0.0179982000
_diffrn_orient_matrix_UB_22      0.0593746000
_diffrn_orient_matrix_UB_23      0.0068707000
_diffrn_orient_matrix_UB_31      0.0655755000
_diffrn_orient_matrix_UB_32      0.0145011000
_diffrn_orient_matrix_UB_33      0.0102468000
_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  0.0640
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22553
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.969
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74564
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0073(16)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     984
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0604P)^2^+0.4471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2759
_reflns_number_total             3383
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc04174k2.cif
_cod_data_source_block           k11107-jjw-d(tpg82)_auto
_cod_database_code               7251694
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim N1 \\sim N2 \\sim O1: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C20(H20)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              59740
_shelx_hkl_checksum              42099
_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 1.857
_oxdiff_exptl_absorpt_empirical_full_min 0.581