A three-component 1,3-dipolar cycloaddition of pyrazolone-derived azomethine ylides with succinimides for the construction of novel spiro-pyrazolone-pyrrolizines containing succinimides.
Xu, Jianming; Hu, Dan; Wang, Jian; Hu, Song; Yin, Heng; Li, Yulong; Li, Chenyi; Organic & biomolecular chemistry 24 (2026) 1363–1368; doi:10.1039/d6ob00014b

data_7160937
_publ_section_title
;
 A three-component 1,3-dipolar cycloaddition of pyrazolone-derived
 azomethine ylides with succinimides for the construction of novel
 spiro-pyrazolone-pyrrolizines containing succinimides.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1363
_journal_page_last               1368
_journal_paper_doi               10.1039/d6ob00014b
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C24 H22 N4 O3'
_chemical_formula_sum            'C24 H22 N4 O3'
_chemical_formula_weight         414.45
_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             2025-05-13
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-05-21 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                103.680(3)
_cell_angle_beta                 97.729(3)
_cell_angle_gamma                93.013(3)
_cell_formula_units_Z            8
_cell_length_a                   12.3346(10)
_cell_length_b                   13.8998(12)
_cell_length_c                   25.5746(19)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.28
_cell_volume                     4205.4(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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0798
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            99529
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_min         1.951
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1503 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.8088.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1121
_refine_ls_number_reflns         20873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+1.0331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12085
_reflns_number_total             20873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00014b2.cif
_cod_data_source_block           mo_250513lcy_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7160937
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C32(H32), C33(H33), C61(H61), C81(H81), C80(H80), C59(H59),
 C87(H87), C39(H39), C12(H12), C62(H62)
2.b Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C42(H42A,H42B), C88(H88A,H88B), C90(H90A,H90B), C15(H15A,
 H15B), C13(H13A,H13B), C89(H89A,H89B), C63(H63A,H63B), C40(H40A,H40B),
 C14(H14A,H14B), C41(H41A,H41B), C64(H64A,H64B)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C68(H68), C51(H51), C53(H53), C20(H20), C44(H44), C24(H24),
 C75(H75), C3(H3), C48(H48), C50(H50), C92(H92), C27(H27), C72(H72), C54(H54),
 C49(H49), C93(H93), C45(H45), C2(H2), C96(H96), C21(H21), C30(H30), C1(H1),
 C47(H47), C69(H69), C94(H94), C46(H46), C70(H70), C5(H5), C26(H26), C25(H25),
 C95(H95), C22(H22), C23(H23), C6(H6), C71(H71), C74(H74), C73(H73), C77(H77),
 C78(H78)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C84(H84A,H84B,H84C), C58(H58A,H58B,H58C), C18(H18A,H18B,
 H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'