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_7219661
_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            'C24 H44 N2 O'
_chemical_formula_weight         376.61
_chemical_name_systematic        5-n-hexadecyl-1-(tetrahydropyran-2-yl)pyrazole
_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   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-12-18 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                92.436(3)
_cell_angle_beta                 91.591(3)
_cell_angle_gamma                104.178(3)
_cell_formula_units_Z            4
_cell_length_a                   8.7407(5)
_cell_length_b                   9.4611(5)
_cell_length_c                   29.7000(15)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.29
_cell_volume                     2377.3(2)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.999
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            60311
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.713
_diffrn_reflns_theta_min         2.223
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7212
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol, water'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0500P)^2^+0.3880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5456
_reflns_number_total             8085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra00837a2.cif
_cod_data_source_block           5-n-hexadecyl-1-(tetrahydropyran-2-yl)pyrazole
_cod_database_code               7219661
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2014/6
_shelx_res_checksum              72971
_shelx_hkl_checksum              2445