Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles.
Chalyk, Bohdan A.; Khutorianskyi, Andrii; Lysenko, Andrii; Fil, Yulia; Kuchkovska, Yuliya O.; Gavrilenko, Konstantin S.; Bakanovych, Iulia; Moroz, Yurii S.; Gorlova, Alina O.; Grygorenko, Oleksandr O.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02258

data_4034706
_publ_section_title
;
 Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles
 and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02258
_journal_year                    2019
_chemical_formula_moiety         'C5 H3 F2 N O3'
_chemical_formula_sum            'C5 H3 F2 N O3'
_chemical_formula_weight         163.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                84.307(15)
_cell_angle_beta                 83.682(14)
_cell_angle_gamma                78.046(15)
_cell_formula_units_Z            2
_cell_length_a                   5.093(2)
_cell_length_b                   5.618(2)
_cell_length_c                   11.155(5)
_cell_measurement_reflns_used    461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      3.69
_cell_volume                     309.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4960
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         1.842
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1414
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.070
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0976P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                974
_reflns_number_total             1414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02258_si_003.cif
_cod_data_source_block           xr26rt
_cod_database_code               4034706
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              5316
_shelx_hkl_checksum              29779