Multicomponent Coupling Reaction of Perfluoroarenes with 1,3-Butadiene and Aryl Grignard Reagents Promoted by an Anionic Ni(II) Complex.
Iwasaki, Takanori; Fukuoka, Asuka; Min, Xin; Yokoyama, Wataru; Kuniyasu, Hitoshi; Kambe, Nobuaki; Organic letters 18 (2016) 4868–4871; doi:10.1021/acs.orglett.6b02343

data_1555750
_publ_section_title
;
 Multicomponent Coupling Reaction of Perfluoroarenes with 1,3-Butadiene
 and Aryl Grignard Reagents Promoted by an Anionic Ni(II) Complex.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4868
_journal_page_last               4871
_journal_paper_doi               10.1021/acs.orglett.6b02343
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H32 Li1 O8 1+, C14 H17 Ni 1-'
_chemical_formula_sum            'C30 H49 Li Ni O8'
_chemical_formula_weight         603.35
_chemical_melting_point          298
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                86.3290(8)
_cell_angle_beta                 78.9210(8)
_cell_angle_gamma                74.0440(8)
_cell_formula_units_Z            2
_cell_length_a                   8.67174(16)
_cell_length_b                   12.0843(2)
_cell_length_c                   15.4857(3)
_cell_measurement_reflns_used    26147
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.69
_cell_measurement_theta_min      3.81
_cell_volume                     1531.07(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31816
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        71.690
_diffrn_reflns_theta_max         71.690
_diffrn_reflns_theta_min         3.805
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.298
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     506
_refine_ls_number_reflns         5807
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.3525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                5020
_reflns_number_total             5807
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b02343_si_002.cif
_cod_data_source_block           NiPhC8H12_LiC16H32O8
_cod_database_code               1555750