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_7161071
_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            'C24 H16 D6 F3 N O5 S'
_chemical_formula_weight         499.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_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                 92.219(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1549(7)
_cell_length_b                   16.3136(13)
_cell_length_c                   16.7975(14)
_cell_measurement_reflns_used    9002
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.74
_cell_volume                     2233.0(3)
_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 0.995
_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  0.0571
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38520
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         4.234
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         14240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0577P)^2^+0.9523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                11435
_reflns_number_total             14240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01918d2.cif
_cod_data_source_block           zv1763
_cod_depositor_comments
'Adding full bibliography for 7161069--7161075.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7161071
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              78381