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_4034707
_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         'C6 H5 F2 N O3'
_chemical_formula_sum            'C6 H5 F2 N O3'
_chemical_formula_weight         177.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 119.429(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.197(3)
_cell_length_b                   6.3032(12)
_cell_length_c                   14.879(3)
_cell_measurement_reflns_used    804
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.72
_cell_volume                     1404.7(5)
_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      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7378
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.720
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_description       prizm
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.9539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1308
_reflns_number_total             1622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02258_si_004.cif
_cod_data_source_block           xr128
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034707
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              83324
_shelx_hkl_checksum              45515