Preparation of 5-Fluoropyrazoles from Pyrazoles and N-Fluorobenzenesulfonimide (NFSI).
Levchenko, Vitalina; Dmytriv, Yurii V.; Tymtsunik, Andriy V.; Liubchak, Konstantin; Rudnichenko, Alexander; Melnyk, Anton V.; Veselovych, Stanislav Y.; Borodulin, Yurii V.; Otsalyuk, Oleksandr M.; Tolmachev, Andrei A.; Mykhailiuk, Pavel K.; The Journal of organic chemistry 83 (2018) 3265–3274; doi:10.1021/acs.joc.8b00199

data_4035158
_publ_section_title
;
 Preparation of 5-Fluoropyrazoles from Pyrazoles and
 N-Fluorobenzenesulfonimide (NFSI).
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3265
_journal_page_last               3274
_journal_paper_doi               10.1021/acs.joc.8b00199
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C15 H18 B F N2 O2'
_chemical_formula_weight         288.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.49(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.051(3)
_cell_length_b                   13.168(4)
_cell_length_c                   25.958(7)
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      3.3
_cell_volume                     4772(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            50643
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         3.193
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       stick
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         13841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.2324
_refine_ls_R_factor_gt           0.0797
_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^)+(0.0934P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4715
_reflns_number_total             13841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00199_si_001.cif
_cod_data_source_block           tolm275
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035158
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              65995
_shelx_hkl_checksum              54841