Deoxofluorination of Aliphatic Carboxylic Acids: a Route to Trifluoromethyl-Substituted Derivatives.
Bugera, Maksym; Trofymchuk, Serhii; Tarasenko, Karen; Zaporozhets, Olga; Pustovit, Yurii; Mykhailiuk, Pavel K.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02596

data_4037619
_publ_section_title
;
 Deoxofluorination of Aliphatic Carboxylic Acids: a Route to
 Trifluoromethyl-Substituted Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02596
_journal_year                    2019
_chemical_absolute_configuration none
_chemical_formula_moiety         'C5 H6 F3 N O'
_chemical_formula_sum            'C5 H6 F3 N O'
_chemical_formula_weight         153.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 113.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.400(4)
_cell_length_b                   6.986(4)
_cell_length_c                   10.481(6)
_cell_measurement_reflns_used    262
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      22.27
_cell_measurement_theta_min      3.75
_cell_volume                     633.0(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      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3297
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.472
_diffrn_reflns_theta_min         2.113
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.4044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                923
_reflns_number_total             1133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02596_si_005.cif
_cod_data_source_block           xr99
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4037619
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.920
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              98296
_shelx_hkl_checksum              16262