The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic anhydrides: an unusual approach to pyrrolo[3,4-<i>c</i>]pyridine derivatives, possessing anti-inflammatory activity.
Zaytsev, Vladimir P.; Simakova, Daria N.; Maslova, Viktoria S.; Ilyushenkova, Valentina V.; Novikov, Roman A.; Grigoriev, Mikhail S.; Danilov, Roman D.; Litvinov, Roman; Kolesnik, Irina A.; Potkin, Vladimir I.; Zubkov, Fedor I.; Organic & biomolecular chemistry 23 (2025) 3925–3936; doi:10.1039/d5ob00040h

data_7160432
_publ_section_title
;
 The IMDAV reaction between 3-(isoxazol-3-yl)allylamines and maleic
 anhydrides: an unusual approach to pyrrolo[3,4-<i>c</i>]pyridine
 derivatives, possessing anti-inflammatory activity.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3925
_journal_page_last               3936
_journal_paper_doi               10.1039/d5ob00040h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C23 H19 F3 N2 O2'
_chemical_formula_weight         412.40
_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_method           SHELXL-2018/3
_audit_update_record
;
2024-04-24 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.408(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4100(14)
_cell_length_b                   27.059(7)
_cell_length_c                   13.460(3)
_cell_measurement_reflns_used    347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      12.81
_cell_measurement_theta_min      3.38
_cell_volume                     1958.1(8)
_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  0.3564
_diffrn_reflns_av_unetI/netI     0.3764
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14588
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         4.079
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.820
_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            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.263
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         3447
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.3628
_refine_ls_R_factor_gt           0.1167
_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^)+(0.0990P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2072
_refine_ls_wR_factor_ref         0.3037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                881
_reflns_number_total             3447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00040h2.cif
_cod_data_source_block           P67
_cod_depositor_comments
'Adding full bibliography for 7160429--7160433.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160432
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              73676