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_4514221
_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         'C17 H10 F4 O2 S2'
_chemical_formula_sum            'C17 H10 F4 O2 S2'
_chemical_formula_weight         386.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7206(3)
_cell_length_b                   10.8574(4)
_cell_length_c                   19.0756(7)
_cell_measurement_reflns_used    9197
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.517
_cell_measurement_theta_min      2.638
_cell_volume                     1599.02(10)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73947
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.9222.
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    1.605
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0354P)^2^+0.9021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3407
_reflns_number_total             3669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs7b02618_si_006.cif
_cod_data_source_block           s
_cod_depositor_comments
'Adding full bibliography for 4514218--4514221.cif.'
_cod_database_code               4514221
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'