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_4034708
_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 H8 F2 N2 O'
_chemical_formula_sum            'C6 H8 F2 N2 O'
_chemical_formula_weight         162.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 105.295(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.914(4)
_cell_length_b                   10.509(5)
_cell_length_c                   9.039(5)
_cell_measurement_reflns_used    697
_cell_measurement_temperature    138(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.67
_cell_volume                     725.1(6)
_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      138(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.454
_diffrn_reflns_theta_min         2.668
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.004
_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^+0.4833P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                998
_reflns_number_total             1488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02258_si_002.cif
_cod_data_source_block           xr25
_cod_original_cell_volume        725.1(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034708
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              10609
_shelx_hkl_checksum              92501