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_4037864
_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 H11 Cl F3 N O2'
_chemical_formula_weight         221.61
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 109.386(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8335(11)
_cell_length_b                   9.7817(6)
_cell_length_c                   8.4036(7)
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.1499
_cell_measurement_theta_min      3.3012
_cell_volume                     917.58(14)
_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 0.979
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4257
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_min         3.308
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0938P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             4257
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03011_si_003.cif
_cod_data_source_block           t125
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037864
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              17863
_shelx_hkl_checksum              36881