Fluoroalkyl Amino Reagents for the Introduction of the Fluoro(trifluoromethoxy)methyl Group onto Arenes and Heterocycles.
Schmitt, Etienne; Bouvet, Sébastien; Pégot, Bruce; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergii; Magnier, Emmanuel; Leroux, Frédéric R; Organic letters 19 (2017) 4960–4963; doi:10.1021/acs.orglett.7b02444

data_1547590
_publ_section_title
;
 Fluoroalkyl Amino Reagents for the Introduction of the
 Fluoro(trifluoromethoxy)methyl Group onto Arenes and Heterocycles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4960
_journal_page_last               4963
_journal_paper_doi               10.1021/acs.orglett.7b02444
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C8 H8 F4 N2 O4'
_chemical_formula_sum            'C8 H8 F4 N2 O4'
_chemical_formula_weight         272.16
_chemical_name_systematic
'Ethyl 5-amino-3-(fluoro(trifluoromethoxy)methyl)isoxazole-4-carboxylate'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                91.196(4)
_cell_angle_beta                 99.999(3)
_cell_angle_gamma                115.544(3)
_cell_formula_units_Z            4
_cell_length_a                   8.8731(13)
_cell_length_b                   9.0666(13)
_cell_length_c                   15.314(2)
_cell_measurement_reflns_used    3557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.70
_cell_volume                     1088.3(3)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.964
_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  0.0854
_diffrn_reflns_av_unetI/netI     0.1579
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16308
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.504
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.2389
_refine_ls_R_factor_gt           0.1115
_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^)+(0.0712P)^2^+2.2445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2229
_reflns_number_total             5064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02444_si_002.cif
_cod_data_source_block           fles160524
_cod_database_code               1547590
_shelx_estimated_absorpt_t_min   0.918
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              16678
_shelx_hkl_checksum              21589