Base-controlled diastereoselective [3+2]-cycloaddition and Michael addition of isatin ketonitrones and chalcones to construct spiropyrrolidine oxoindoles and γ-substituted isatin ketonitrones
Chen, Silu; Ma, Lan; Yue, Chao; Du, Biao; Lu, Cuifen; Long, Chunyan; Wu, Wanbing; Li, Sicheng; He, Qiao; Yue, Guizhou; New Journal of Chemistry 49 (2025) 16978–16988; doi:10.1039/D5NJ02378E

data_7063967
_publ_section_title
;
 Base-controlled diastereoselective [3+2]-cycloaddition and Michael
 addition of isatin ketonitrones and chalcones to construct
 spiropyrrolidine oxoindoles and \g-substituted isatin ketonitrones
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16978
_journal_page_last               16988
_journal_paper_doi               10.1039/D5NJ02378E
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C37 H30 N2 O3, C2 H6 O'
_chemical_formula_sum            'C39 H36 N2 O4'
_chemical_formula_weight         596.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0741(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7995(4)
_cell_length_b                   18.6988(7)
_cell_length_c                   14.2020(5)
_cell_measurement_reflns_used    6730
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.43
_cell_volume                     3125.56(19)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30464
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.178
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0686 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.4167.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6285
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0614P)^2^+1.4264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                5609
_reflns_number_total             6285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02378e2.cif
_cod_data_source_block           mo_0214_1_0m
_cod_depositor_comments
'Adding full bibliography for 7063967--7063968.cif.'
_cod_database_code               7063967
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C38(H38A,H38B)
2.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C12(H12), C33(H33), C1(H1A), C5(H5), C30(H30), C27(H27), C2(H2),
 C34(H34), C16(H16), C23(H23), C14(H14), C15(H15), C28(H28), C13(H13), C21(H21),
  C19(H19), C36(H36), C35(H35), C22(H22), C29(H29), C3(H3), C4(H4), C20(H20)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_shelx_res_checksum              60741
_olex2_submission_special_instructions 'No special instructions were received'