Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions.
Iwasaki, Takanori; Fukuoka, Asuka; Yokoyama, Wataru; Min, Xin; Hisaki, Ichiro; Yang, Tao; Ehara, Masahiro; Kuniyasu, Hitoshi; Kambe, Nobuaki; Chemical science 9 (2018) 2195–2211; doi:10.1039/c7sc04675h

data_1548615
_publ_section_title
;
 Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard
 reagents in the presence of 1,3-butadiene: mechanistic studies of
 four-component coupling and competing cross-coupling reactions.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              2195
_journal_page_last               2211
_journal_paper_doi               10.1039/c7sc04675h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety
'C16 H21 Ni, C16 H32 Li O8, 0.5(C5H12) 0.25(C4 H8 O)'
_chemical_formula_sum            'C35.5 H61 Li Ni O8.25'
_chemical_formula_weight         685.51
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-09-02 deposited with the CCDC.
2018-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                67.4550(7)
_cell_angle_beta                 88.5760(7)
_cell_angle_gamma                85.7540(7)
_cell_formula_units_Z            8
_cell_length_a                   11.4664(2)
_cell_length_b                   24.2697(4)
_cell_length_c                   28.3765(5)
_cell_measurement_reflns_used    97000
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.73
_cell_measurement_theta_min      3.05
_cell_volume                     7273.2(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.968
_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  0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            177793
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         71.874
_diffrn_reflns_theta_min         3.050
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2968.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF, pentane, 12-crown-4'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.99
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     1643
_refine_ls_number_reflns         27611
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1745
_refine_ls_R_factor_gt           0.1017
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1940P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2986
_refine_ls_wR_factor_ref         0.3607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11890
_reflns_number_total             27611
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7sc04675h2.cif
_cod_data_source_block           8
_cod_depositor_comments
;

2019-07-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 1548615.cif.
;
_cod_original_formula_moiety
'4 (C16 H21 Ni) 4 (C16 H32 O8) 2 (C5H12) C4 H8 O'
_cod_original_formula_sum        'C142 H244 Li4 Ni4 O33'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     2742.03
_cod_database_code               1548615
_shelx_res_checksum              56137