Hydrodefluorination of functionalized fluoroaromatics with triethylphosphine: a theoretical and experimental study
Facundo, Aldo A.; Arévalo, Alma; Fundora-Galano, Gabriela; Flores-Álamo, Marcos; Orgaz, Emilio; García, Juventino J.; New Journal of Chemistry 43 (2019) 6897–; doi:10.1039/C9NJ00721K

data_7058261
_publ_section_title
;
 Hydrodefluorination of functionalized fluoroaromatics with
 triethylphosphine: a theoretical and experimental study
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6897
_journal_paper_doi               10.1039/C9NJ00721K
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C12 H15 F4 P S'
_chemical_formula_sum            'C12 H15 F4 P S'
_chemical_formula_weight         298.27
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-06-22T12:12:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-10-16 deposited with the CCDC.    2019-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1337(12)
_cell_length_b                   10.3273(10)
_cell_length_c                   10.8935(12)
_cell_measurement_reflns_used    1408
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.499
_cell_measurement_theta_min      6.553
_cell_volume                     1365.0(2)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material
;    
        'WinGX publication routines (Farrugia, 1999)'                 
    L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;
_computing_structure_refinement
;
      'SHELXS-2014 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_structure_solution
;
      'SHELXS-2014 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0465792
_diffrn_orient_matrix_UB_12      0.0410077
_diffrn_orient_matrix_UB_13      0.0055516
_diffrn_orient_matrix_UB_21      -0.0352396
_diffrn_orient_matrix_UB_22      -0.0545554
_diffrn_orient_matrix_UB_23      -0.0051834
_diffrn_orient_matrix_UB_31      0.0012281
_diffrn_orient_matrix_UB_32      -0.0078885
_diffrn_orient_matrix_UB_33      0.0646889
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5780
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.755
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.605
_diffrn_reflns_theta_min         3.741
_exptl_absorpt_coefficient_mu    0.38
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0394P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.63
_reflns_number_gt                2231
_reflns_number_total             2905
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00721k2.cif
_cod_data_source_block           aa491
_cod_depositor_comments          'Adding full bibliography for 7058261.cif.'
_cod_database_code               7058261
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.978