Convergent and divergent synthesis of dihydroisoquinoline-1,4-diones enabled by a photocatalytic skeleton-editing [4 + 2] strategy
Du, Hai-Wu; Jia, Jun-Song; Chen, Xiao-Yi; Yuan, Zhang-Yin; Lin, Jia-Ni; Li, Yu-Long; Yu, Qiong; Shu, Wei; Chemical Science 16 (2025) 11833–11840; doi:10.1039/D5SC00665A

data_1574701
_publ_section_title
;
 Convergent and divergent synthesis of dihydroisoquinoline-1,4-diones
 enabled by a photocatalytic skeleton-editing [4 + 2] strategy
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              11833
_journal_page_last               11840
_journal_paper_doi               10.1039/D5SC00665A
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C26 H25 N O2'
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.47
_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             2024-01-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-06-07 deposited with the CCDC.	2025-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                79.694(2)
_cell_angle_beta                 74.868(2)
_cell_angle_gamma                68.162(2)
_cell_formula_units_Z            8
_cell_length_a                   13.8148(7)
_cell_length_b                   17.2854(8)
_cell_length_c                   19.6680(9)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.17
_cell_measurement_theta_min      3.79
_cell_volume                     4190.8(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            79250
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.381
_diffrn_reflns_theta_min         2.337
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.0555
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5463
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1280 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.7249.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1088
_refine_ls_number_reflns         16344
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+1.2302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1463
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12102
_reflns_number_total             16344
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00665a2.cif
_cod_data_source_block           dhw512602_0m
_cod_depositor_comments
'Adding full bibliography for 1574700--1574701.cif.'
_cod_database_code               1574701
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C70A-C67 \\sim C70-C67 \\sim C69-C67 \\sim C69A-C67 \\sim C68-C67 \\sim
C68A-C67
 with sigma of 0.02
3. Others
 Sof(C70A)=Sof(H70D)=Sof(H70E)=Sof(H70F)=Sof(C69A)=Sof(H69D)=Sof(H69E)=
 Sof(H69F)=Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=1-FVAR(1)
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=
 Sof(C69)=Sof(H69A)=Sof(H69B)=Sof(H69C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C40(H40A,H40B), C92(H92A,H92B), C66(H66A,H66B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), N4(H4A), N3(H3), N1(H1), C36(H36), C11(H11), C34(H34), C75(H75),
 C88(H88), C62(H62), C8(H8), C104(H104), C4(H4), C31(H31), C35(H35), C77(H77),
 C76(H76), C101(H101), C9(H9), C103(H103), C78(H78), C102(H102), C37(H37),
 C63(H63), C60(H60), C26(H26), C10(H10), C49(H49), C5(H5), C89(H89), C87(H87),
 C30(H30), C23(H23), C52(H52), C3(H3A), C25(H25), C29(H29), C61(H61), C1(H1A),
 C50(H50), C24(H24), C86(H86), C51(H51), C56(H56), C57(H57), C27(H27), C83(H83),
  C2(H2), C82(H82), C28(H28), C55(H55), C54(H54), C53(H53), C80(H80), C81(H81),
 C79(H79)
4.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C18(H18A,H18B,H18C), C42(H42A,H42B,H42C), C17(H17A,H17B,
 H17C), C44(H44A,H44B,H44C), C16(H16A,H16B,H16C), C96(H96A,H96B,H96C), C95(H95A,
 H95B,H95C), C94(H94A,H94B,H94C), C68(H68A,H68B,H68C), C70(H70A,H70B,H70C),
 C69(H69A,H69B,H69C), C70A(H70D,H70E,H70F), C69A(H69D,H69E,H69F), C68A(H68D,
 H68E,H68F)
;
_olex2_submission_special_instructions 'No special instructions were received'