I2-DMSO mediated multi-component cascade cyclization to construct pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6-one skeleton
Song, Yu-Man; Wang, Li-Sheng; Zhou, You; Tang, Yong-Xing; Wu, Chun-Yan; Wu, Yan-Dong; Wu, An-Xin; RSC Advances 15 (2025) 28280–28284; doi:10.1039/D5RA04871K

data_7250788
_publ_section_title
;
 I2-DMSO mediated multi-component cascade cyclization to construct
 pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6-one skeleton
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              28280
_journal_page_last               28284
_journal_paper_doi               10.1039/D5RA04871K
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C21 H16 N4 O2'
_chemical_formula_sum            'C21 H16 N4 O2'
_chemical_formula_weight         356.38
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-07-12
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2025-02-12 deposited with the CCDC.	2025-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.435(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.613(3)
_cell_length_b                   10.293(2)
_cell_length_c                   11.665(3)
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.42
_cell_volume                     1749.3(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14808
_diffrn_reflns_theta_full        27.84
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         1.40
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.2247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                2889
_reflns_number_total             4127
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ra04871k2.cif
_cod_data_source_block           y
_cod_original_cell_volume        1749.2(6)
_cod_database_code               7250788
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), 
 C18(H18), C19(H19), C20(H20), C21(H21) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O2(H2A) 
;
_olex2_submission_special_instructions 'No special instructions were received'