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_7161072
_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_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-10-13 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.882(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   8.0310(5)
_cell_length_c                   16.2960(11)
_cell_measurement_reflns_used    5030
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.40
_cell_measurement_theta_min      3.18
_cell_volume                     1604.29(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26484
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         4.183
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       fragment
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.229
_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
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0557P)^2^+0.3168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3448
_reflns_number_total             4675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01918d2.cif
_cod_data_source_block           ZV2253
_cod_depositor_comments
'Adding full bibliography for 7161069--7161075.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7161072
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              49950