Base-catalyzed stereoselective synthesis of (<i>Z</i>)-6-arylidenedihydropyrano[2,3-<i>c</i>]pyrazoles <i>via</i> 6-<i>exo-dig</i> oxy-cyclization with pyrazolones and 4-tosyl-1,3-enynes.
Banda, Bhanu Prasad; Gurla, Nikhitha; Nanubolu, Jagadeesh Babu; Atmakur, Krishnaiah; Organic & biomolecular chemistry 24 (2026) 1716–1721; doi:10.1039/d5ob01881a

data_7160972
_publ_section_title
;
 Base-catalyzed stereoselective synthesis of
 (<i>Z</i>)-6-arylidenedihydropyrano[2,3-<i>c</i>]pyrazoles <i>via</i>
 6-<i>exo-dig</i> oxy-cyclization with pyrazolones and 4-tosyl-1,3-enynes.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1716
_journal_page_last               1721
_journal_paper_doi               10.1039/d5ob01881a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C26 H19 F N2 O'
_chemical_formula_sum            'C26 H19 F N2 O'
_chemical_formula_weight         394.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-11-26 deposited with the CCDC.	2026-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1319(9)
_cell_length_b                   7.4931(6)
_cell_length_c                   41.107(3)
_cell_measurement_reflns_used    2446
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.489
_cell_measurement_theta_min      2.516
_cell_volume                     4044.9(5)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            17671
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.517
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene and isopropanol'
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.1182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1644
_reflns_number_total             3534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01881a2.cif
_cod_data_source_block           KB1802_0m
_cod_depositor_comments          'Adding full bibliography for 7160972.cif.'
_cod_database_code               7160972
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              99237