Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction for the synthesis of benzo-, carbocyclo-, thienothiopheneisoindolecarboxylic acids and its limitations.
Yakovleva, Elizaveta D.; Shelukho, Evgeniya R.; Nadirova, Maryana A.; Erokhin, Pavel P.; Simakova, Daria N.; Khrustalev, Victor N.; Grigoriev, Mikhail S.; Novikov, Anton P.; Romanycheva, Anna A.; Shetnev, Anton A.; Bychkova, Olga P.; Trenin, Alexey S.; Zubkov, Fedor I.; Zaytsev, Vladimir P.; Organic & biomolecular chemistry 22 (2024) 2643–2653; doi:10.1039/d3ob01933k

data_7159833
_publ_section_title
;
 Application of the intramolecular Diels-Alder vinylarene (IMDAV) reaction
 for the synthesis of benzo-, carbocyclo-,
 thienothiopheneisoindolecarboxylic acids and its limitations.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2643
_journal_page_last               2653
_journal_paper_doi               10.1039/d3ob01933k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H25 N O3 S, 0.5(C2 D6 O S)'
_chemical_formula_sum            'C24 H25 D3 N O3.5 S1.5'
_chemical_formula_weight         437.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-21 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                74.286(2)
_cell_angle_beta                 80.082(2)
_cell_angle_gamma                71.936(2)
_cell_formula_units_Z            4
_cell_length_a                   11.1667(8)
_cell_length_b                   13.3681(10)
_cell_length_c                   15.9013(13)
_cell_measurement_reflns_used    7364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.86
_cell_volume                     2162.2(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.1141
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            58286
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.974
_diffrn_reflns_theta_min         3.732
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9099
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       plate
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         9374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0402P)^2^+1.2660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5899
_reflns_number_total             9374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01933k2.cif
_cod_data_source_block           ZV2115
_cod_depositor_comments
;
Adding full bibliography for 7159828--7159834.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H50 D6 N2 O7 S3'
_cod_original_formula_weight         875.16
_cod_original_formula_moiety         '2(C23 H25 N O3 S), C2 D6 O S'
_cod_original_formula_units_Z            2
_cod_database_code               7159833
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C3A(H3AA), C12(H12B), C12A(H12A), C33A(H33C), C42(H42B), C42A(H42A)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B),
  C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B)
1.c Me refined with riding coordinates:
 C61(D61A,D61B,D61C), C62(D62A,D62B,D62C)
1.d Aromatic/amide H refined with riding coordinates:
 C22(H22A), C23(H23A), C24(H24A), C25(H25A), C26(H26A), C52(H52A), C53(H53A),
 C54(H54A), C55(H55A), C56(H56A)
;
_shelx_res_checksum              83021
_olex2_submission_special_instructions 'No special instructions were received'