Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction for the synthesis of benzo-and carbocyclofuroisoindolecarboxylic acids and its limitations
Yakovleva, Elizaveta D.; Shelukho, Evgeniya; Erokhin, Pavel; Ilyushenkova, Valentina; Guryeva, Aleksandra S.; Logvinenko, Nikita; Khrustalev, Victor N.; Grigoriev, Mikhail S.; Zubkov, Fedor Ivanovich; Zaytsev, Vladimir P.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01918D

data_7161073
_publ_section_title
;
 Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction
 for the synthesis of benzo- and carbocyclofuroisoindole carboxylic acids
 and its limitations.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3274
_journal_page_last               3286
_journal_paper_doi               10.1039/d5ob01918d
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
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_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2025-12-07 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.948
_cell_measurement_theta_min      4.437
_cell_volume                     3251.9(2)
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_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
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_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
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_diffrn_measured_fraction_theta_max 0.990
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'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -23
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
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_diffrn_reflns_theta_min         4.433
_diffrn_source                   'micro-focus sealed X-ray tube'
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.118a (Rigaku Oxford Diffraction, 2025).
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.25
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_refine_diff_density_max         0.619
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0630P)^2^+4.8386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3223
_reflns_number_total             3513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01918d2.cif
_cod_data_source_block           12a
_cod_depositor_comments
'Adding full bibliography for 7161069--7161075.cif.'
_cod_original_cell_volume        3251.93(19)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7161073
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.828
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              54780