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_4037617
_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 ad
_chemical_formula_moiety         'K(ClO4)5, 4(C6 H11 F3 N), 1.26 (H2 O)'
_chemical_formula_sum            'C24 H46.52 Cl5 F12 K N4 O21.27'
_chemical_formula_weight         1175.84
_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                 130.76
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.336(8)
_cell_length_b                   7.0039(17)
_cell_length_c                   17.870(6)
_cell_measurement_reflns_used    566
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      19.23
_cell_measurement_theta_min      2.30
_cell_volume                     2212.3(12)
_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       'phi and 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  0.0695
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10320
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         1.745
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_description       needle
_exptl_crystal_F_000             1201
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.442
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1177P)^2^+2.8865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3086
_reflns_number_total             3857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02596_si_003.cif
_cod_data_source_block           xr33
_cod_original_cell_volume        2212.2(12)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4037617
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              47509
_shelx_hkl_checksum              48207