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_7159834
_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         'C21 H16 Br N O3 S, C2 D6 O S'
_chemical_formula_sum            'C23 H16 Br D6 N O4 S2'
_chemical_formula_weight         526.48
_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                 97.701(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5933(6)
_cell_length_b                   12.7117(5)
_cell_length_c                   12.7881(5)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.81
_cell_measurement_theta_min      3.02
_cell_volume                     2189.78(16)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0715
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            80424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.423
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  0.730
_exptl_absorpt_correction_T_min  0.650
_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    1.597
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0273P)^2^+1.3269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5087
_reflns_number_total             6368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01933k2.cif
_cod_data_source_block           zv2209
_cod_depositor_comments
'Adding full bibliography for 7159828--7159834.cif.'
_cod_database_code               7159834
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.730
_shelx_estimated_absorpt_t_min   0.487
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C3A(H3C), C10(H10A), C10A(H10B)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
1.c Me refined with riding coordinates:
 C18(D18A,D18B,D18C), C19(D19A,D19B,D19C)
1.d Aromatic/amide H refined with riding coordinates:
 C6(H6A), C7(H7A), C8(H8A), C9(H9A), C12(H12A), C13(H13A), C15(H15A), C16(H16A)
;
_shelx_res_checksum              85057
_olex2_submission_special_instructions 'No special instructions were received'