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_7161070
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N O5, C2 H6 O S'
_chemical_formula_sum            'C23 H29 N O6 S'
_chemical_formula_weight         447.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2025-12-07 deposited with the CCDC.	2026-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                100.0863(15)
_cell_angle_beta                 90.7070(14)
_cell_angle_gamma                90.2151(13)
_cell_formula_units_Z            4
_cell_length_a                   9.14531(17)
_cell_length_b                   11.43369(19)
_cell_length_c                   21.5910(4)
_cell_measurement_reflns_used    19873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.56
_cell_measurement_theta_min      3.92
_cell_volume                     2222.55(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type
'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  0.0542
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30564
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         83.712
_diffrn_reflns_theta_min         3.927
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1108
_refine_ls_number_reflns         11897
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0914
_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^)+(0.0333P)^2^+9.6P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2067
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                11411
_reflns_number_total             11897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01918d2.cif
_cod_data_source_block           12c
_cod_depositor_comments
'Adding full bibliography for 7161069--7161075.cif.'
_cod_database_code               7161070
_shelx_estimated_absorpt_t_min   0.615
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2013-4
_shelx_res_checksum              41544