Synthesis of fused indolin-3-one derivatives <i>via</i> (3 + 2)-cycloaddition of <i>in situ</i> generated 3<i>H</i>-indol-3-one with nitrilimines, nitrile oxides and azomethine ylides.
Arutiunov, Nikolai A.; Zatsepilina, Anna M.; Tolstov, Kirill V.; Shtal, Daria A.; Momotova, Daria S.; Aksenov, Dmitrii A.; Aksenov, Nicolai A.; Aksenov, Alexander V.; Organic & biomolecular chemistry 23 (2025) 9198–9210; doi:10.1039/d5ob01186h

data_7160755
_publ_section_title
;
 Synthesis of fused indolin-3-one derivatives <i>via</i> (3 +
 2)-cycloaddition of <i>in situ</i> generated 3<i>H</i>-indol-3-one with
 nitrilimines, nitrile oxides and azomethine ylides.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9198
_journal_page_last               9210
_journal_paper_doi               10.1039/d5ob01186h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C26 H21 N3 O2'
_chemical_formula_sum            'C26 H21 N3 O2'
_chemical_formula_weight         407.46
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-07-07 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                68.051(4)
_cell_angle_beta                 80.115(3)
_cell_angle_gamma                89.958(3)
_cell_formula_units_Z            4
_cell_length_a                   10.0806(3)
_cell_length_b                   13.6026(5)
_cell_length_c                   16.0009(6)
_cell_measurement_reflns_used    12001
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7520
_cell_measurement_theta_min      5.4890
_cell_volume                     2000.00(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.90 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.5684
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -72.00  33.00   1.00    1.02    --  -40.44  71.00-174.00  105
  2  \w   -114.00  -9.00   1.00    1.02    --  -40.44 -71.00  54.00  105
  3  \w      9.00 114.00   1.00    1.02    --   40.44  71.00-174.00  105
  4  \w    -33.00  72.00   1.00    1.02    --   40.44 -71.00  54.00  105
  5  \w     81.00 178.00   1.00    4.08    --  112.00  71.00-174.00   97
  6  \w     38.00 143.00   1.00    4.08    --  112.00 -71.00  54.00  105
  7  \w   -120.00   1.00   1.00    1.02    --  -40.44 -19.00 -90.00  121
  8  \w      6.00  80.00   1.00    1.02    --   40.44 -99.00-120.00   74
  9  \w     16.00 115.00   1.00    1.02    --   40.44  38.00 -30.00   99
 10  \w      5.00  31.00   1.00    1.02    --   40.44  86.00  39.44   26
 11  \w      7.00  42.00   1.00    1.02    --   40.44  79.00 -13.67   35
 12  \w     39.00 109.00   1.00    4.08    --  112.00-111.00-180.00   70
 13  \w    103.00 178.00   1.00    4.08    --  112.00  77.00 150.00   75
 14  \w     39.00 109.00   1.00    4.08    --  112.00-111.00 -30.00   70
 15  \w     30.00 106.00   1.00    4.08    --  112.00 -95.00  60.00   76
 16  \w     39.00 109.00   1.00    4.08    --  112.00-111.00 150.00   70
 17  \w     86.00 178.00   1.00    4.08    --  112.00  45.00 -90.00   92
 18  \w     39.00 138.00   1.00    4.08    --  112.00 -45.00-180.00   99
 19  \w     39.00 138.00   1.00    4.08    --  112.00 -45.00-180.00   99
 20  \w     61.00 146.00   1.00    4.08    --  112.00 178.00  30.00   85
 21  \w    104.00 178.00   1.00    4.08    --  112.00 111.00 150.00   74
 22  \w     34.00 146.00   1.00    4.08    --  112.00 -81.00 143.83  112
 23  \w     61.00 146.00   1.00    4.08    --  112.00 178.00 -60.00   85
 24  \w    103.00 178.00   1.00    4.08    --  112.00  77.00 120.00   75
 25  \w     39.00 109.00   1.00    4.08    --  112.00-111.00   0.00   70
 26  \w    103.00 178.00   1.00    4.08    --  112.00  77.00   0.00   75
 27  \w     86.00 178.00   1.00    4.08    --  112.00  45.00 -60.00   92
 28  \w     39.00 109.00   1.00    4.08    --  112.00-111.00 120.00   70
 29  \w    102.00 129.00   1.00    4.08    --  112.00 -45.00 120.00   27
 30  \w     40.00  65.00   1.00    4.08    --  112.00 -95.00  30.00   25
 31  \w     70.00 105.00   1.00    4.08    --  112.00 -95.00  30.00   35
 32  \w     77.00 112.00   1.00    4.08    --  112.00 -45.00  30.00   35
 33  \w     41.00 123.00   1.00    4.08    --  112.00 -61.00-180.00   82
 34  \w     62.00  95.00   1.00    4.08    --  112.00 178.00  30.00   33
 35  \w    105.00 166.00   1.00    4.08    --  112.00 111.00-150.00   61
 36  \w    125.00 174.00   1.00    4.08    --  112.00  45.00-150.00   49
 37  \w    102.00 138.00   1.00    4.08    --  112.00 -45.00 -30.00   36
 38  \w     80.00 109.00   1.00    4.08    --  112.00-111.00-120.00   29
 39  \w    107.00 137.00   1.00    4.08    --  112.00 -45.00-150.00   30
 40  \w    105.00 142.00   1.00    4.08    --  112.00 111.00  60.00   37
 41  \w     49.00  76.00   1.00    4.08    --  112.00 -45.00 -30.00   27
 42  \w     41.00  81.00   1.00    4.08    --  112.00 -61.00 -90.00   40
 43  \w    104.00 160.00   1.00    4.08    --  112.00  77.00-150.00   56
 44  \w     33.00  60.00   1.00    4.08    --  112.00 -15.00  60.00   27
 45  \w    116.00 162.00   1.00    4.08    --  112.00 -15.00  60.00   46
 46  \w     77.00 106.00   1.00    4.08    --  112.00-111.00-150.00   29
 47  \w     81.00 108.00   1.00    4.08    --  112.00-111.00 -90.00   27
 48  \w     55.00 109.00   1.00    4.08    --  112.00-111.00  90.00   54
 49  \w    108.00 135.00   1.00    4.08    --  112.00  77.00-120.00   27
 50  \w     41.00  68.00   1.00    4.08    --  112.00 -95.00 120.00   27
 51  \w     87.00 177.00   1.00    4.08    --  112.00  45.00 150.00   90
 52  \w     83.00 158.00   1.00    4.08    --  112.00  61.00-180.00   75
 53  \w     39.00 109.00   1.00    4.08    --  112.00-111.00  30.00   70
 54  \w    110.00 137.00   1.00    4.08    --  112.00 -77.00 -60.00   27
 55  \w     97.00 124.00   1.00    4.08    --  112.00 -81.00-125.61   27
 56  \w    102.00 129.00   1.00    4.08    --  112.00 -82.00 176.56   27
 57  \w    131.00 167.00   1.00    4.08    --  112.00 111.00  90.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1120907000
_diffrn_orient_matrix_UB_12      0.0674392000
_diffrn_orient_matrix_UB_13      -0.0423017000
_diffrn_orient_matrix_UB_21      -0.0134840000
_diffrn_orient_matrix_UB_22      0.0495916000
_diffrn_orient_matrix_UB_23      0.0730229000
_diffrn_orient_matrix_UB_31      0.1069335000
_diffrn_orient_matrix_UB_32      0.0893002000
_diffrn_orient_matrix_UB_33      -0.0635163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.1077
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            9943
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.413
_diffrn_reflns_theta_min         3.030
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             856.000
_exptl_crystal_preparation       'Prepared by cycloaddition reaction'
_exptl_crystal_recrystallization_method
'Crystallized by slow evaporation of saturated solution in EtOAc.'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         9943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0596P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7540
_reflns_number_total             9943
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9503\% 
around [0.97 -0.00 0.26] (reciprocal) or [1.00 0.00 -0.00] (direct)
;
_cod_data_source_file            d5ob01186h3.cif
_cod_data_source_block           anna_zam277_2_twin1_hklf5
_cod_depositor_comments
'Adding full bibliography for 7160755--7160757.cif.'
_cod_original_cell_volume        2000.00(13)
_cod_database_code               7160755
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C26H21N3O2
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5540(11)
 0.4460(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C16(H16), C42(H42)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17(H17A,H17B), C45(H45A,H45B), C18(H18A,H18B), C44(H44A,
 H44B), C43(H43A,H43B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C47(H47), C14(H14), C5(H5), C21(H21), C11(H11), C51(H51),
 C4(H4), C48(H48), C13(H13), C37(H37), C3(H3A), C41(H41), C49(H49), C38(H38),
 C12(H12), C39(H39), C29(H29), C24(H24), C31(H31), C50(H50), C30(H30), C32(H32),
  C22(H22), C23(H23)
;
_shelx_res_checksum              6259
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.763
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2