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_7159832
_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         'C22 H15 F4 N O3 S, C2 D6 O S'
_chemical_formula_sum            'C24 H15 D6 F4 N O4 S2'
_chemical_formula_weight         533.57
_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_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                90
_cell_angle_beta                 94.633(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2769(3)
_cell_length_b                   11.7542(3)
_cell_length_c                   32.9548(9)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      3.36
_cell_volume                     4740.0(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            55760
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.722
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         10839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0524P)^2^+0.9098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6501
_reflns_number_total             10839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01933k2.cif
_cod_data_source_block           Pok90
_cod_depositor_comments
'Adding full bibliography for 7159828--7159834.cif.'
_cod_database_code               7159832
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.869
_olex2_refinement_description
;
1. Shared sites
{C1, C1C}
{C2, C2C}
{C3, C3C}
{C4, C4C}
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1C)
Uanis(C2) = Uanis(C2C)
Uanis(C3) = Uanis(C3C)
Uanis(C4) = Uanis(C4C)
3. Others
 Sof(S1)=Sof(S2)=Sof(C1)=Sof(D1A)=Sof(D1B)=Sof(D1C)=Sof(C2)=Sof(D2A)=Sof(D2B)=
 Sof(D2C)=Sof(C3)=Sof(D3A)=Sof(D3B)=Sof(D3C)=Sof(C4)=Sof(D4A)=Sof(D4B)=Sof(D4C)=
 1-FVAR(1)
 Sof(S1C)=Sof(S2C)=Sof(C1C)=Sof(D1D)=Sof(D1E)=Sof(D1F)=Sof(C2C)=Sof(D2D)=
 Sof(D2E)=Sof(D2F)=Sof(C3C)=Sof(D3D)=Sof(D3E)=Sof(D3F)=Sof(C4C)=Sof(D4D)=
 Sof(D4E)=Sof(D4F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3AA(H3B), C9BA(H9B), C10C(H10A), C3AB(H3H), C9BB(H9D), C10D(H10B)
4.b Secondary CH2 refined with riding coordinates:
 C3A(H3C,H3D), C3B(H3G,H3F)
4.c Me refined with riding coordinates:
 C1(D1A,D1B,D1C), C2(D2A,D2B,D2C), C3(D3A,D3B,D3C), C4(D4A,D4B,D4C), C1C(D1D,
 D1E,D1F), C2C(D2D,D2E,D2F), C3C(D3D,D3E,D3F), C4C(D4D,D4E,D4F)
4.d Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C14A(H14A), C15A(H15A),
 C17A(H17A), C18A(H18A), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9C),
 C14B(H14B), C15B(H15B), C17B(H17B), C18B(H18B)
;
_shelx_res_checksum              76812
_olex2_submission_special_instructions 'No special instructions were received'