Catalytic system-controlled divergent reactions of pyrazolidinones with 3-alkynyl-3-hydroxyisoindolinones to construct diversified nitrogen-containing heterocyclic scaffolds
Zhang, Zhenwei; Zhang, Xiaoxue; Wang, Hao; Xie, Geyao; Zhou, Yu; RSC Advances 15 (2025) 21872–21878; doi:10.1039/D5RA01992C

data_7250595
_publ_section_title
;
 Catalytic system-controlled divergent reactions of pyrazolidinones with
 3-alkynyl-3-hydroxyisoindolinones to construct diversified
 nitrogen-containing heterocyclic scaffolds
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              21872
_journal_page_last               21878
_journal_paper_doi               10.1039/D5RA01992C
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         '2(C27 H25 N3 O2), H2 O'
_chemical_formula_sum            'C54 H52 N6 O5'
_chemical_formula_weight         865.01
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_audit_update_record
;
2025-04-30 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.3740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9888(2)
_cell_length_b                   18.4115(5)
_cell_length_c                   12.1884(3)
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      74.38
_cell_measurement_theta_min      4.53
_cell_volume                     2326.32(10)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Bruker APEX III'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22292
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.618
_diffrn_reflns_theta_min         4.265
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.7356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1260 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.7920.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4691
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.1021
_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^)+13.0500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2347
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             4691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra01992c4.cif
_cod_data_source_block           cu_20221176_0m
_cod_database_code               7250595
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O3(0.5) H3B(0.5) H3C(0.5)
3.a Free rotating group:
 O3(H3B,H3C)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C18(H18), C22(H22), C3(H3A), C9(H9), C21(H21), C12(H12),
 C16(H16), C6(H6), C5(H5), C19(H19), C4(H4), C20(H20), C13(H13), C15(H15),
 C14(H14)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'