Synthesis of 5-(pyrazol-4-yl) pentanoic acids and 4-(pyrazol-4-yl) butanoic acids via a cascade annulation/ring-opening reaction between hydrazone and dienone
Nayak, Kalinga H.; Jijin, Robert K.; Babu, Beneesh P.; RSC Advances 15 (2025) 24137–24141; doi:10.1039/D5RA03561A

data_7250677
_publ_section_title
;
 Synthesis of 5-(pyrazol-4-yl) pentanoic acids and 4-(pyrazol-4-yl)
 butanoic acids via a cascade annulation/ring-opening reaction between
 hydrazone and dienone
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              24137
_journal_page_last               24141
_journal_paper_doi               10.1039/D5RA03561A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C35 H32 N2 O4'
_chemical_formula_sum            'C35 H32 N2 O4'
_chemical_formula_weight         544.62
_chemical_melting_point          463
_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   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-07-19 deposited with the CCDC.	2025-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                74.888(2)
_cell_angle_beta                 83.416(2)
_cell_angle_gamma                74.210(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7430(5)
_cell_length_b                   11.8023(6)
_cell_length_c                   15.3997(8)
_cell_measurement_reflns_used    7341
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      20.81
_cell_measurement_theta_min      2.42
_cell_volume                     1474.58(14)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36504
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.019
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane-Methanol mixture'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         7347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0925P)^2^+0.4470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.2343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3367
_reflns_number_total             7347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra03561a2.cif
_cod_data_source_block           KSH_3_184_050324_0m_a
_cod_database_code               7250677
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              17660