On the catalytic hydrodefluorination of fluoroaromatics using nickel complexes: the true role of the phosphine.
Arévalo, Alma; Tlahuext-Aca, Adrian; Flores-Alamo, Marcos; García, Juventino J; Journal of the American Chemical Society 136 (2014) 4634–4639; doi:10.1021/ja412268y

data_4121529
_publ_section_title
;
 On the catalytic hydrodefluorination of fluoroaromatics using nickel
 complexes: the true role of the phosphine.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4634
_journal_page_last               4639
_journal_paper_doi               10.1021/ja412268y
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H33 F5 Ni1 P2'
_chemical_formula_sum            'C20 H33 F5 Ni P2'
_chemical_formula_weight         489.11
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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
_audit_creation_date             2012-11-05T18:36:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                74.385(9)
_cell_angle_beta                 72.833(8)
_cell_angle_gamma                83.760(8)
_cell_formula_units_Z            1
_cell_length_a                   7.5958(6)
_cell_length_b                   8.2688(9)
_cell_length_c                   9.8593(9)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      67.9835
_cell_measurement_theta_min      4.844
_cell_measurement_wavelength     0.71073
_cell_volume                     569.53(10)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0086098
_diffrn_orient_matrix_UB_12      -0.1801436
_diffrn_orient_matrix_UB_13      -0.0184041
_diffrn_orient_matrix_UB_21      -0.1028011
_diffrn_orient_matrix_UB_22      0.0613504
_diffrn_orient_matrix_UB_23      -0.1188175
_diffrn_orient_matrix_UB_31      0.1856444
_diffrn_orient_matrix_UB_32      0.035291
_diffrn_orient_matrix_UB_33      -0.1186025
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3581
_diffrn_reflns_theta_full        68.1
_diffrn_reflns_theta_max         68.1
_diffrn_reflns_theta_min         4.85
_exptl_absorpt_coefficient_mu    2.955
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
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            'pale brown'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.4304
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.1545
_refine_diff_density_max         1.686
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1093P)^2^+0.4640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1639
_reflns_number_gt                2181
_reflns_number_total             2418
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja412268y_si_002.cif
_cod_data_source_block           5
_cod_original_cell_volume        569.53(9)
_cod_database_code               4121529