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_7160433
_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            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2034(17)
_cell_length_b                   6.2396(5)
_cell_length_c                   22.4373(18)
_cell_measurement_reflns_used    2596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.20
_cell_measurement_theta_min      3.24
_cell_volume                     3248.5(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
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'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22620
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         4.129
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.898
_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_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1018
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1198P)^2^+7.4342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2458
_refine_ls_wR_factor_ref         0.2764
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3967
_reflns_number_total             5945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00040h2.cif
_cod_data_source_block           13a_LT
_cod_depositor_comments
'Adding full bibliography for 7160429--7160433.cif.'
_cod_database_code               7160433
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              98057