Mild and Efficient Ni-Catalyzed Biaryl Synthesis with Polyfluoroaryl Magnesium Species: Verification of the Arrest State, Uncovering the Hidden Competitive Second Transmetalation and Ligand-Accelerated Highly Selective Monoarylation
Wang, Junya; Meng, Ge; Xie, Kun; Li, Liting; Sun, Huaming; Huang, Zhiyan; ACS Catalysis 7 (2017) 7421–; doi:10.1021/acscatal.7b02618

data_4514220
_publ_section_title
;
 Mild and Efficient Ni-Catalyzed Biaryl Synthesis with Polyfluoroaryl
 Magnesium Species: Verification of the Arrest State, Uncovering the
 Hidden Competitive Second Transmetalation and Ligand-Accelerated Highly
 Selective Monoarylation
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7421
_journal_paper_doi               10.1021/acscatal.7b02618
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C48 H30 F8 Ni O P2'
_chemical_formula_sum            'C48 H30 F8 Ni O P2'
_chemical_formula_weight         895.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.6323(16)
_cell_length_b                   11.1626(4)
_cell_length_c                   19.9766(8)
_cell_measurement_reflns_used    9284
_cell_measurement_temperature    273
_cell_measurement_theta_max      68.284
_cell_measurement_theta_min      4.958
_cell_volume                     8837.6(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            196654
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.716
_diffrn_reflns_theta_min         4.114
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1150 before and 0.0859 after correction. The Ratio of minimum to maximum transmission is 0.8091. The \l/2 correction factor is Not present.'
_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    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8128
_refine_ls_number_restraints     312
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0876P)^2^+1.6916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7110
_reflns_number_total             8128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02618_si_004.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 4514218--4514221.cif.'
_cod_database_code               4514220
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.597
_shelx_estimated_absorpt_t_min   0.448
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C00X, C015, C01G, C01F, C01D, C017, F008, F00C, F00R, F009, C00B, C00E, C00P,
 C010, C00N, C00I, F004, F005, F00A, F006
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C00B \\sim C00I \\sim C00N \\sim C010 \\sim C00P \\sim C00E \\sim F004 \\sim
F006 \\sim F00A \\sim F005 \\sim C00X \\sim C017 \\sim C01D \\sim C01F \\sim
C01G \\sim C015 \\sim F008 \\sim F00C \\sim F00R \\sim F009: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C00X, C015, C01G, C01F, C01D, C017, F008, F00C, F00R, F009, C00B, C00I, C00N,
 C00E, C00P, C010, F006, F004, F00A, F005
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C014(H014), C016(H016), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01E(H01E), C01F(H01F), C01H(H01H), C01I(H01I),
 C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O)
;
_shelx_res_checksum              48751
_shelx_hkl_checksum              97736
_shelx_fab_checksum              36545
_olex2_submission_special_instructions 'No special instructions were received'