Organocatalytic Asymmetric [3 + 3] Annulation Reaction Between 5-Aminopyrazoles and Enynones: Synthesis of Pyrazolo[3,4-b]pyridines
Pan, Subhas Chandra; Sahoo, Dipali Digangana; Chemical Communications  (2026) –; doi:10.1039/D6CC01164K

data_7135641
_publ_section_title
;
 Organocatalytic asymmetric [3+3] annulation reaction between
 5-aminopyrazoles and enynones: synthesis of
 pyrazolo[3,4-<i>b</i>]pyridines.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7369
_journal_page_last               7372
_journal_paper_doi               10.1039/d6cc01164k
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration R
_chemical_formula_sum            'C27 H21 N3'
_chemical_formula_weight         387.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-01-30 deposited with the CCDC.	2026-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.701(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9402(7)
_cell_length_b                   8.5319(5)
_cell_length_c                   11.4283(7)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.91
_cell_measurement_theta_min      2.42
_cell_volume                     1057.10(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0506
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.878
_exptl_absorpt_coefficient_mu    0.071
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3726
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0374P)^2^+0.1394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2802
_reflns_number_total             3726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc01164k2.cif
_cod_data_source_block           dds_pyr_yn_chyral_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135641.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135641
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              9011
_shelx_hkl_checksum              81583