A telescoped diastereoselective synthesis of phthalimido-substituted spiro-oxazoline oxindoles via aziridine expansion strategy
Nikolaeva, Anna A.; Filippov, Ilya P.; Polekh, Oleg E.; Pankova, Alena S.; Rostovskii, Nikolai V.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01645B

data_7160904
_publ_section_title
;
 A telescoped diastereoselective synthesis of phthalimido-substituted
 spiro-oxazoline oxindoles via aziridine expansion strategy
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01645B
_journal_year                    2025
_chemical_formula_moiety         '1.143(C25 H17 N3 O4)'
_chemical_formula_sum            'C28.57 H19.43 N3.43 O4.57'
_chemical_formula_weight         483.90
_chemical_name_systematic
2-((3R,5'S)-1-methyl-2-oxo-5'-phenyl-5'H-spiro[indoline-3,2'-oxazol]-5'-yl)isoindoline-1,3-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-10-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            7
_cell_length_a                   10.23700(10)
_cell_length_b                   15.85190(10)
_cell_length_c                   25.2440(2)
_cell_measurement_reflns_used    20995
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      71.7390
_cell_measurement_theta_min      3.2450
_cell_volume                     4096.49(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (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 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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    -43.00 -18.00   0.50    0.25    --  -41.10  59.00  38.00   50
  2  \w   -115.00 -87.00   0.50    0.25    --  -41.10 177.00-108.00   56
  3  \w    -75.00 -50.00   0.50    0.25    --  -41.10 -63.00 100.00   50
  4  \w    -63.00 -38.00   0.50    0.25    --  -41.10 114.00 114.00   50
  5  \w    -84.00 -50.00   0.50    0.25    --  -41.10 -59.00-101.00   68
  6  \w     40.00  65.00   0.50    0.25    --   41.10  63.00-123.00   50
  7  \w     64.00  92.00   0.50    0.25    --   41.10  59.00  38.00   56
  8  \w    -15.00  36.00   0.50    0.25    --   41.10 -63.00 100.00  102
  9  \w     -2.00  35.00   0.50    0.25    --   41.10-114.00  23.00   74
 10  \w     57.00 116.00   0.50    0.25    --   41.10-177.00-113.00  118
 11  \w     89.00 116.00   0.50    1.00    --  100.00 177.00-108.00   54
 12  \w     96.00 122.00   0.50    1.00    --  100.00  63.00-123.00   52
 13  \w     95.00 120.00   0.50    1.00    --  100.00 114.00 114.00   50
 14  \w     82.00 137.00   0.50    1.00    --  100.00  59.00  38.00  110
 15  \w     39.00  68.00   0.50    1.00    --  100.00 -59.00-101.00   58
 16  \w     54.00  79.00   0.50    1.00    --  100.00 -63.00 100.00   50
 17  \w     54.00  80.00   0.50    1.00    --  100.00-114.00  23.00   52
 18  \w     64.00  90.00   0.50    0.25    --   41.10  43.00  30.00   52
 19  \w     31.00  56.00   0.50    0.25    --   41.10  43.00  30.00   50
 20  \w     61.00  91.00   0.50    0.25    --   41.10  32.00  90.00   60
 21  \w     66.00 104.00   0.50    0.25    --   41.10  32.00 -30.00   76
 22  \w     54.00  94.00   0.50    1.00    --  100.00 -25.00  30.00   80
 23  \w     84.00 152.00   0.50    1.00    --  100.00 111.00 -90.00  136
 24  \w    100.00 153.00   0.50    1.00    --  100.00  33.00  30.00  106
 25  \w     84.00 116.00   0.50    1.00    --  100.00 111.00  60.00   64
 26  \w     96.00 157.00   0.50    1.00    --  100.00  25.00-180.00  122
 27  \w     39.00 117.00   0.50    1.00    --  100.00-133.00  60.00  156
 28  \w     58.00  84.00   0.50    1.00    --  100.00 -33.00 120.00   52
 29  \w     88.00 151.00   0.50    1.00    --  100.00  17.00 -90.00  126
 30  \w     37.00 116.00   0.50    1.00    --  100.00 -50.00  30.00  158
 31  \w    125.00 151.00   0.50    1.00    --  100.00  93.00  90.00   52
 32  \w     43.00  68.00   0.50    1.00    --  100.00 177.00-108.00   50
 33  \w    -67.00 -40.00   0.50    0.25    --  -41.10 -32.00  30.00   54
 34  \w    -10.00  15.00   0.50    0.25    --   41.10 -32.00 120.00   50
 35  \w     -1.00  43.00   0.50    0.25    --   41.10 -43.00   0.00   88
 36  \w     17.00  47.00   0.50    0.25    --   41.10 -32.00 120.00   60
 37  \w     91.00 123.00   0.50    1.00    --  100.00  33.00  90.00   64
 38  \w     92.00 122.00   0.50    1.00    --  100.00  25.00 120.00   60
 39  \w     44.00  70.00   0.50    1.00    --  100.00 -93.00  60.00   52
 40  \w     36.00  64.00   0.50    1.00    --  100.00 -77.00 -60.00   56
 41  \w     40.00  66.00   0.50    1.00    --  100.00 -50.00 -60.00   52
 42  \w     91.00 116.00   0.50    1.00    --  100.00 -50.00 -60.00   50
 43  \w     77.00 111.00   0.50    1.00    --  100.00-133.00 120.00   68
 44  \w     81.00 107.00   0.50    1.00    --  100.00-111.00  90.00   52
 45  \w     39.00 106.00   0.50    1.00    --  100.00-111.00 150.00  134
 46  \w     74.00 117.00   0.50    1.00    --  100.00-133.00-120.00   86
 47  \w    100.00 126.00   0.50    1.00    --  100.00  17.00  30.00   52
 48  \w     91.00 138.00   0.50    1.00    --  100.00  33.00 -60.00   94
 49  \w    127.00 147.00   0.50    1.00    --  100.00  17.00  30.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0889626000
_diffrn_orient_matrix_UB_12      0.0347897000
_diffrn_orient_matrix_UB_13      0.0441132000
_diffrn_orient_matrix_UB_21      -0.0557221000
_diffrn_orient_matrix_UB_22      0.0890830000
_diffrn_orient_matrix_UB_23      -0.0092362000
_diffrn_orient_matrix_UB_31      -0.1078136000
_diffrn_orient_matrix_UB_32      -0.0173593000
_diffrn_orient_matrix_UB_33      0.0411418000
_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  0.0352
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27665
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.848
_diffrn_reflns_theta_min         3.502
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
_exptl_crystal_recrystallization_method
'Single crystals were grown by slow evaporation of its solution in dimethyl ether-hexane-DCM mixture.'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0434P)^2^+1.4786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3749
_reflns_number_total             3997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01645b2.cif
_cod_data_source_block           fip17
_cod_database_code               7160904
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H17 N3 O4'
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 94.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              3696
_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 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.697