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_1574700
_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 H24 Br N O2'
_chemical_formula_sum            'C26 H24 Br N O2'
_chemical_formula_weight         462.37
_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             2024-03-23
_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                90
_cell_angle_beta                 103.9270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1999(2)
_cell_length_b                   8.1197(2)
_cell_length_c                   22.7110(5)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.70
_cell_measurement_theta_min      3.73
_cell_volume                     2183.61(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27244
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.697
_diffrn_reflns_theta_min         3.733
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.8418.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0231
_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^)+(0.0288P)^2^+1.5093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4214
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00665a2.cif
_cod_data_source_block           dhw202403215q_0m
_cod_depositor_comments
'Adding full bibliography for 1574700--1574701.cif.'
_cod_database_code               1574700
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.922
_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.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C16(H16), C17(H17), C3(H3), C20(H20), C19(H19),
 C26(H26), C23(H23), C22(H22), C25(H25), C24(H24)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              54346
_olex2_submission_special_instructions 'No special instructions were received'