Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides.
Simonetti, Marco; Perry, Gregory J. P.; Cambeiro, Xacobe C.; Juliá-Hernández, Francisco; Arokianathar, Jude N.; Larrosa, Igor; Journal of the American Chemical Society 138 (2016) 3596–3606; doi:10.1021/jacs.6b01615

data_4130259
_publ_section_title
;
 Ru-Catalyzed C-H Arylation of Fluoroarenes with Aryl Halides.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3596
_journal_page_last               3606
_journal_paper_doi               10.1021/jacs.6b01615
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C30 H54 N6 Ru, 4(B0.5 F2)'
_chemical_formula_sum            'C30 H54 B2 F8 N6 Ru'
_chemical_formula_weight         773.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           50
_space_group_name_Hall           '-P 2ab 2b'
_space_group_name_H-M_alt        'P b a n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-23
_audit_creation_method
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Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8977(3)
_cell_length_b                   34.0657(11)
_cell_length_c                   11.0451(4)
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      25.6580
_cell_measurement_theta_min      3.5840
_cell_volume                     4100.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1428
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details
;
  1 omega  -68.00  -35.00   1.0000    3.2700
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  114.0000  130.0000 33

  2 omega  -89.00   21.00   1.0000    3.2700
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  -19.0000   60.0000 110

  3 omega   -9.00   56.00   1.0000    3.2700
omega____ theta____ kappa____ phi______ frames
    -       18.7038  -99.0000  -30.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0071537000
_diffrn_orient_matrix_UB_12      -0.0016650000
_diffrn_orient_matrix_UB_13      0.0636101000
_diffrn_orient_matrix_UB_21      0.0117121000
_diffrn_orient_matrix_UB_22      -0.0204411000
_diffrn_orient_matrix_UB_23      -0.0037598000
_diffrn_orient_matrix_UB_31      0.0636408000
_diffrn_orient_matrix_UB_32      0.0035867000
_diffrn_orient_matrix_UB_33      0.0078787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16335
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.324
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0468P)^2^+5.3371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2890
_reflns_number_total             4871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b01615_si_002.cif
_cod_data_source_block           ail9
_cod_original_sg_symbol_H-M      'P b a n'
_cod_database_code               4130259
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         RuN6C40B2F8
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-F2 \\sim F4-F7 \\sim F4-F5 \\sim F5-F7 \\sim F5-F2 \\sim F7-F2
 with sigma of 0.02
 F4-B4 \\sim F5-B4 \\sim F2-B4 \\sim F7-B4 \\sim F20-B25 \\sim F24-B25 \\sim
F1-B2 \\sim F3-B2
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
F4 \\sim F7 \\sim F2 \\sim F5: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 F5, F2, B4, F4, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F20(0.5) F24(0.5) B25(0.25) F5(0.25) F2(0.25) F7(0.25) F4(0.25)
6.a Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              8935
_shelx_hkl_checksum              76757
_olex2_submission_special_instructions 'No special instructions were received'