Bis(diisopropylphosphinomethyl)amine Nickel(II) and Nickel(0) Complexes: Coordination Chemistry, Reactivity, and Catalytic Decarbonylative C–H Arylation of Benzoxazole
Kruckenberg, Achim; Wadepohl, Hubert; Gade, Lutz H.; Organometallics 32 (2013) 5153–; doi:10.1021/om400711d

data_4081440
_publ_section_title
;
 Bis(diisopropylphosphinomethyl)amine Nickel(II) and Nickel(0) Complexes:
 Coordination Chemistry, Reactivity, and Catalytic Decarbonylative C--H
 Arylation of Benzoxazole
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5153
_journal_paper_doi               10.1021/om400711d
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C17 H39 N Ni P2'
_chemical_formula_sum            'C17 H39 N Ni P2'
_chemical_formula_weight         378.14
_chemical_properties_physical    air-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ak50
_audit_creation_date
;
'Mon Jan 21 13:25:06 2013'
;
_audit_update_record             'Fri Jun 21 16:59:33 CEST 2013'
_cell_angle_alpha                90
_cell_angle_beta                 90.4571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.68141(6)
_cell_length_b                   14.47778(9)
_cell_length_c                   14.90719(9)
_cell_measurement_reflns_used    51639
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      32.0890
_cell_measurement_theta_min      3.7190
_cell_volume                     2089.40(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -28.00   -2.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026  -78.0000 -164.0000 52

  2 omega  -60.00   20.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   78.0000  -15.0000 160

  3 omega  -58.00  -32.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   77.0000  -60.0000 52

  4 omega  -41.00   -1.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026  -77.0000  -30.0000 80

  5 omega  -60.00  -34.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   78.0000  140.0000 52

  6 omega    9.00   97.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000   60.0000 176

  7 omega   -7.00   33.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -57.0000 -180.0000 80

  8 omega  -43.00   -1.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -78.0000 -164.0000 84

  9 omega   67.00   93.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000  120.0000 52

 10 omega   33.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -78.0000 -164.0000 54

 11 omega  -43.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000  120.0000 206

 12 omega   -4.00   98.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000  -60.0000 204

 13 omega   13.00   40.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   38.0000  -30.0000 54

 14 omega  -26.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -78.0000   39.0000 172

 15 omega    4.00   99.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000 -180.0000 190

 16 omega   -4.00   32.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000  120.0000 72

 17 omega   31.00   58.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   19.0000  -60.0000 54

 18 omega    1.00   77.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   38.0000 -180.0000 152

 19 omega   34.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000  -60.0000 52

 20 omega  -41.00   32.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -57.0000  -90.0000 146

 21 omega  -50.00   41.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   57.0000 -150.0000 182

 22 omega  -50.00   41.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   57.0000   90.0000 182

 23 omega  -97.00   -6.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026  -57.0000   60.0000 182

 24 omega  -48.00    3.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026  -78.0000 -164.0000 102

 25 omega  -50.00   41.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026   57.0000  -60.0000 182

 26 omega  -48.00    3.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.0026  -78.0000   39.0000 102

 27 omega    6.00   97.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000    0.0000 182

 28 omega    1.00  101.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   38.0000  120.0000 200

 29 omega  -43.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -78.0000   39.0000 206

 30 omega  -43.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -78.0000 -164.0000 206

 31 omega    1.00  101.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   38.0000 -150.0000 200

 32 omega  -41.00   50.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -57.0000 -120.0000 182

 33 omega  -45.00   55.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -38.0000   60.0000 200

 34 omega   -4.00   99.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   77.0000 -150.0000 206

 35 omega    6.00   97.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000 -150.0000 182

 36 omega    6.00   97.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  -30.0000 182

 37 omega    6.00   74.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026   57.0000  150.0000 136

 38 omega  -43.00   60.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0026  -77.0000  120.0000 206

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      -0.0044335000
_diffrn_orient_matrix_UB_12      -0.0480858000
_diffrn_orient_matrix_UB_13      -0.0086354000
_diffrn_orient_matrix_UB_21      -0.0399038000
_diffrn_orient_matrix_UB_22      -0.0058471000
_diffrn_orient_matrix_UB_23      0.0392794000
_diffrn_orient_matrix_UB_31      -0.0613135000
_diffrn_orient_matrix_UB_32      0.0072724000
_diffrn_orient_matrix_UB_33      -0.0254193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            132702
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.386
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.3446
_exptl_crystal_size_mid          0.1593
_exptl_crystal_size_min          0.0303
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         7315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0182P)^2^+1.0604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6970
_reflns_number_total             7315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak50
_cod_original_cell_volume        2089.41(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4081440
_audit_block_refno               1682
_audit_block_usercomment         'AK579, plate, yellow'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group with stretchable bonds:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C)
;
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.900
_shelx_hkl_checksum              293
_cell_oxdiff_length_a            9.67844(9)
_cell_oxdiff_length_b            14.48058(14)
_cell_oxdiff_length_c            14.90895(12)
_cell_oxdiff_angle_alpha         90.0173(7)
_cell_oxdiff_angle_beta          90.4836(7)
_cell_oxdiff_angle_gamma         90.0096(8)
_cell_oxdiff_volume              2089.41(3)
_cell_oxdiff_measurement_reflns_used 51639
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_theta     30.44
_reflns_odcompleteness_iscentric 1