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_4514219
_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         'C18 H25 Cl F4 Mg O3'
_chemical_formula_sum            'C18 H25 Cl F4 Mg O3'
_chemical_formula_weight         425.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 112.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8663(6)
_cell_length_b                   12.7576(8)
_cell_length_c                   9.7375(6)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    153
_cell_measurement_theta_max      26.488
_cell_measurement_theta_min      2.640
_cell_volume                     1015.01(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      153.0
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16720
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.555
_diffrn_reflns_theta_min         2.493
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1070 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.8907. 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    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.423(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.4766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3906
_reflns_number_total             4161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02618_si_003.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 4514218--4514221.cif.'
_cod_database_code               4514219
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00E(H00C,H00D), C00F(H00E,H00F), C00J(H00H,H00I), C00K(H00J,
 H00K), C00L(H00L,H00M), C00M(H00N,H00O), C00N(H00P,H00Q), C00O(H00R,H00S),
 C00P(H00T,H00U), C00Q(H00V,H00W), C00R(H00X,H00Y)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G)
;
_shelx_res_checksum              51148
_shelx_hkl_checksum              50864
_olex2_submission_special_instructions 'No special instructions were received'