Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel Complexes
Wang-Jun Guo; Zhong-Xia Wang; Journal of Organic Chemistry 78 (2013) 1054–1061; doi:10.1021/jo302425x

data_4027904
_publ_section_title
;
 Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic
 Carbene-Based Nickel Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1054
_journal_page_last               1061
_journal_paper_doi               10.1021/jo302425x
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C40 H40 Br N4 Ni P'
_chemical_formula_weight         746.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                86.910(2)
_cell_angle_beta                 79.6010(10)
_cell_angle_gamma                68.9970(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6574(11)
_cell_length_b                   11.2128(14)
_cell_length_c                   18.5445(19)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.144
_cell_measurement_theta_min      2.371
_cell_volume                     1843.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9772
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                4008
_reflns_number_total             6399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302425x_si_002.cif
_cod_data_source_block           100117e
_cod_database_code               4027904