Deoxofluorination of (Hetero)aromatic Acids.
Trofymchuk, Serhii; Bugera, Maksym; Klipkov, Anton A.; Razhyk, Bohdan; Semenov, Sergey; Tarasenko, Karen; Starova, Viktoriia S.; Zaporozhets, Olga A.; Tananaiko, Oksana Y.; Alekseenko, Anatoliy N.; Pustovit, Yurii; Kiriakov, Oleksandr; Gerus, Igor I.; Tolmachev, Andrei A.; Mykhailiuk, Pavel K.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03011

data_4037861
_publ_section_title
;
 Deoxofluorination of (Hetero)aromatic Acids.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03011
_journal_year                    2020
_chemical_formula_sum            'C6 H13 Cl F3 N O3'
_chemical_formula_weight         239.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4374(5)
_cell_length_b                   25.6538(9)
_cell_length_c                   7.4152(3)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.512
_cell_measurement_theta_min      3.362
_cell_volume                     2175.71(15)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21377
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.994
_diffrn_reflns_theta_min         3.176
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0623
_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^)+(0.1072P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1800
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03011_si_004.cif
_cod_data_source_block           t264
_cod_database_code               4037861
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              34116
_shelx_hkl_checksum              63166