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_7063968
_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 H29 Br N2 O3'
_chemical_formula_sum            'C37 H29 Br N2 O3'
_chemical_formula_weight         629.53
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2024-04-28 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                70.206(4)
_cell_angle_beta                 89.215(4)
_cell_angle_gamma                73.626(4)
_cell_formula_units_Z            4
_cell_length_a                   12.5390(15)
_cell_length_b                   14.6451(17)
_cell_length_c                   19.265(2)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.117
_cell_measurement_theta_min      2.953
_cell_volume                     3180.6(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            59626
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_min         1.564
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.331
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1641 before and 0.0782 after correction.
The Ratio of minimum to maximum transmission is 0.7863.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         13026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+1.7873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11056
_reflns_number_total             13026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02378e2.cif
_cod_data_source_block           20240416_lgz_0m_sq
_cod_depositor_comments
'Adding full bibliography for 7063967--7063968.cif.'
_cod_original_cell_volume        3180.6(7)
_cod_database_code               7063968
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C16(H16), C53(H53), C60(H60)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C31(H31A,H31B), C46(H46A,H46B), C67(H67A,H67B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C39(H39), C40(H40), C41(H41), C42(H42), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52), C55(H55), C56(H56), C57(H57), C58(H58), C59(H59), C62(H62),
 C63(H63), C64(H64), C65(H65), C66(H66), C70(H70), C71(H71), C73(H73), C74(H74)
;
_shelx_res_checksum              16841
_shelx_fab_checksum              15144
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'