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_7160757
_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         'C21 H14 N2 O2'
_chemical_formula_sum            'C21 H14 N2 O2'
_chemical_formula_weight         326.34
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-03
_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                90
_cell_angle_beta                 95.6470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1565(2)
_cell_length_b                   9.31590(10)
_cell_length_c                   15.0212(2)
_cell_measurement_reflns_used    15889
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6000
_cell_measurement_theta_min      3.9190
_cell_volume                     1553.62(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_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 0.998
_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    -81.00  15.00   1.00    1.00    --  -41.19  99.00 124.00   96
  2  \w      6.00  81.00   1.00    1.00    --   41.19 -99.00  18.00   75
  3  \w    104.00 178.00   1.00    1.00    --  112.00  99.00 124.00   74
  4  \w     32.00 107.00   1.00    1.00    --  112.00 -99.00  18.00   75
  5  \w   -115.00 -17.00   1.00    1.00    --  -41.19 -38.00-180.00   98
  6  \w      7.00  33.00   1.00    1.00    --   41.19  84.00-110.63   26
  7  \w     17.00 115.00   1.00    1.00    --   41.19  38.00  60.00   98
  8  \w     17.00 115.00   1.00    1.00    --   41.19  38.00  60.00   98
  9  \w     39.00 109.00   1.00    1.00    --  112.00-111.00 120.00   70
 10  \w    103.00 178.00   1.00    1.00    --  112.00  77.00  90.00   75
 11  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 -90.00   85
 12  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 120.00   99
 13  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00  30.00  109
 14  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00  30.00  109
 15  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00   0.00   99
 16  \w     39.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   70
 17  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 120.00   94
 18  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 120.00   94
 19  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 20  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   76
 21  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 22  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 120.00   99
 23  \w    103.00 178.00   1.00    1.00    --  112.00  77.00-180.00   75
 24  \w     59.00 178.00   1.00    1.00    --  112.00  15.00   0.00  119
 25  \w     59.00 178.00   1.00    1.00    --  112.00  15.00   0.00  119
 26  \w     39.00  89.00   1.00    1.00    --  112.00 -45.00   0.00   50
 27  \w     66.00 100.00   1.00    1.00    --  112.00 178.00 -90.00   34
 28  \w    139.00 177.00   1.00    1.00    --  112.00  30.00  90.00   38
 29  \w     44.00  90.00   1.00    1.00    --  112.00 -45.00  60.00   46
 30  \w     48.00  73.00   1.00    1.00    --  112.00-111.00 -30.00   25
 31  \w     73.00  98.00   1.00    1.00    --  112.00-111.00   0.00   25
 32  \w     68.00  94.00   1.00    1.00    --  112.00 -50.00-123.82   26
 33  \w    114.00 140.00   1.00    1.00    --  112.00 111.00   0.00   26
;
_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      -0.1204404000
_diffrn_orient_matrix_UB_12      0.0493976000
_diffrn_orient_matrix_UB_13      -0.0495706000
_diffrn_orient_matrix_UB_21      0.0550829000
_diffrn_orient_matrix_UB_22      0.1484644000
_diffrn_orient_matrix_UB_23      -0.0157019000
_diffrn_orient_matrix_UB_31      0.0414676000
_diffrn_orient_matrix_UB_32      -0.0535344000
_diffrn_orient_matrix_UB_33      -0.0889696000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.935
_diffrn_reflns_theta_min         3.982
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.896
_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 yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0400P)^2^+0.6790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3121
_reflns_number_total             3234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01186h3.cif
_cod_data_source_block           anna_ark1114_1
_cod_depositor_comments
'Adding full bibliography for 7160755--7160757.cif.'
_cod_database_code               7160757
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.738
_reflns_odcompleteness_completeness 98.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C8(H8), C6(H6), C15(H15), C21(H21), C17(H17), C14(H14),
 C12(H12), C7(H7), C13(H13), C20(H20), C19(H19), C18(H18)
;
_shelx_res_checksum              74988
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.810