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_7250597
_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         'C H2 Cl2, 2(C27 H23 N3 O2)'
_chemical_formula_sum            'C55 H48 Cl2 N6 O4'
_chemical_formula_weight         927.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_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                 102.8130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0724(3)
_cell_length_b                   41.3599(10)
_cell_length_c                   16.7154(4)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      74.73
_cell_measurement_theta_min      2.91
_cell_volume                     9486.7(4)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            150635
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.918
_diffrn_reflns_theta_min         2.136
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0842 after correction.
The Ratio of minimum to maximum transmission is 0.7458.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             3888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.243(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2430
_refine_ls_number_reflns         36461
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0810P)^2^+1.8516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1531
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.881
_reflns_number_gt                28963
_reflns_number_total             36461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra01992c4.cif
_cod_data_source_block           cu_20221175_0m
_cod_database_code               7250597
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.789
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.757(14)
 0.243(14)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C260(H26A,H26B), C248(H24A,H24B), C84(H84A,H84B), C144(H14A,
 H14B), C101(H10A,H10B), C188(H18A,H18B), C207(H20A,H20B), C073(H07A,H07B),
 C127(H12C,H12D), C124(H12A,H12B), C290(H29A,H29B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N283(H283), N60(H60), N115(H115), N230(H230), N159(H159), N218(H218),
 N164(H164), C150(H150), C113(H113), C14(H14), C18(H18), C19(H19), C161(H161),
 C153(H153), C278(H278), C213(H213), C236(H236), C253(H253), C10(H10), C70(H70),
  C73(H73), C77(H77), C257(H257), C92(H92), C89(H89), C234(H234), C172(H172),
 C68(H68), C66(H66), C132(H132), C267(H267), C121(H121), C271(H271), C155(H155),
  C140(H140), C130(H130), C241(H241), C277(H277), C154(H154), C137(H137),
 C110(H110), C239(H239), C95(H95), C119(H119), C9(H9), C276(H276), C91(H91),
 C286(H286), C232(H232), C93(H93), C275(H275), C141(H141), C108(H108),
 C156(H156), C131(H131), C7(H7), C69(H69), C24(H24), C240(H240), C67(H67),
 C288(H288), C8(H8), C23(H23), C111(H111), C139(H139), C235(H235), C223(H223),
 C109(H109), C287(H287), C138(H138), C90(H90), C233(H233), C285(H285),
 C274(H274), C26(H26), C88(H88), C94(H94), C220(H220), C176(H176), C120(H120),
 C170(H170), C112(H112), C25(H25), C118(H118), C200(H200), C15(H15), C175(H175),
  C270(H270), C201(H201), C74(H74), C242(H242), C167(H167), C187(H187),
 C221(H221), C177(H177), C179(H179), C204(H204), C184(H184), C16(H16),
 C254(H254), C178(H178), C168(H168), C169(H169), C222(H222), C195(H195),
 C203(H203), C202(H202), C75(H75), C255(H255), C17(H17), C186(H186), C269(H269),
  C224(H224), C76(H76), C185(H185), C268(H268), C256(H256), C194(H194),
 C225(H225)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C250(H25D,H25E,H25F), C289(H28A,H28B,H28C), C193(H19A,H19B,
 H19C), C86(H86A,H86B,H86C), C3(H3A,H3B,H3C), C148(H14C,H14D,H14E), C258(H25A,
 H25B,H25C), C106(H10C,H10D,H10E), C212(H21A,H21B,H21C), C211(H21D,H21E,H21F),
 C192(H19D,H19E,H19F), C85(H85A,H85B,H85C), C249(H24C,H24D,H24E), C105(H10F,
 H10G,H10H), C149(H14F,H14G,H14H)
;
_olex2_submission_special_instructions 'No special instructions were received'