Facile synthesis of spiro-pyrazolone-tetrahydrofurans/pyrans: ipso-cyclization of arylidene pyrazolones with haloalcohols
Gond, Kavyashree Kuppayya; Maddani, Mahagundappa Rachappa; New Journal of Chemistry 48 (2024) 8667–8671; doi:10.1039/D4NJ00447G

data_7063178
_publ_section_title
;
 Facile synthesis of spiro-pyrazolone-tetrahydrofurans/pyrans:
 ipso-cyclization of arylidene pyrazolones with haloalcohols
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8667
_journal_page_last               8671
_journal_paper_doi               10.1039/D4NJ00447G
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
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_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2024-01-16 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
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_cell_formula_units_Z            4
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.50
_cell_measurement_theta_min      4.50
_cell_volume                     1722.50(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.062
_diffrn_reflns_theta_min         4.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0564P)^2^+0.0312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3062
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00447g2.cif
_cod_data_source_block           kg-245_auto
_cod_depositor_comments
'Adding full bibliography for 7063178--7063179.cif.'
_cod_database_code               7063178
_shelx_estimated_absorpt_t_min   0.717
_shelx_estimated_absorpt_t_max   0.932
_shelxl_version_number           2014-1
_shelx_res_checksum              69226