Green Protection of Pyrazole, Thermal Isomerization and Deprotection of Tetrahydropyranylpyrazoles, and High-Yield, One-Pot Synthesis of 3(5)-Alkylpyrazoles
Ahmed, Basil Mohammed; Mezei, Gellert; RSC Adv.  (2015) –; doi:10.1039/C5RA00837A

data_7219660
_publ_section_title
;
 Green Protection of Pyrazole, Thermal Isomerization and Deprotection of
 Tetrahydropyranylpyrazoles, and High-Yield, One-Pot Synthesis of
 3(5)-Alkylpyrazoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA00837A
_journal_year                    2015
_chemical_formula_sum            'C12 H20 N4 O'
_chemical_formula_weight         236.32
_chemical_name_systematic        1,6-bis(pyrazol-3(5)-yl)hexane
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-12-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                107.833(3)
_cell_angle_beta                 93.710(4)
_cell_angle_gamma                114.352(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8013(4)
_cell_length_b                   9.2025(4)
_cell_length_c                   10.1004(5)
_cell_measurement_reflns_used    4164
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.04
_cell_measurement_theta_min      2.61
_cell_volume                     692.06(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 1.000
_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  0.0697
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13883
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.119
_diffrn_reflns_theta_min         2.604
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water, methanol'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0473
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1433
_reflns_number_total             2194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00837a2.cif
_cod_data_source_block           1,6-bis(pyrazol-3-yl)hexane-hydrate
_cod_database_code               7219660
_shelxl_version_number           2013-2
_shelx_res_checksum              70583
_shelx_hkl_checksum              46410