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_4081433
_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         'C23 H45 N Ni P2'
_chemical_formula_sum            'C23 H45 N Ni P2'
_chemical_formula_weight         456.25
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ak25
_audit_creation_date
;
'Thu Jan 05 15:03:58 2012'
;
_audit_update_record             'Thu Jul  4 10:27:02 CEST 2013'
_cell_angle_alpha                89.652(3)
_cell_angle_beta                 82.032(3)
_cell_angle_gamma                85.869(3)
_cell_formula_units_Z            4
_cell_length_a                   8.1001(3)
_cell_length_b                   14.4306(4)
_cell_length_c                   21.9136(8)
_cell_measurement_reflns_used    11606
_cell_measurement_temperature    115(1)
_cell_measurement_theta_max      25.6262
_cell_measurement_theta_min      3.1862
_cell_volume                     2530.13(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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      115(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9241
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   38.00   85.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   57.0000   30.0000 94

  2 omega    2.00   87.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   57.0000  120.0000 170

  3 omega  -51.00   40.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255  -57.0000  -30.0000 182

  4 omega   -9.00   86.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   77.0000 -150.0000 190

  5 omega  -49.00   40.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255  -57.0000  150.0000 178

  6 omega  -11.00   61.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   77.0000  -30.0000 144

  7 omega  -47.00   47.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255  -77.0000   90.0000 188

  8 omega  -40.00   50.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255  -80.0000 -115.0000 180

  9 omega  -51.00   40.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255  -57.0000 -120.0000 182

 10 omega   -7.00   91.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   38.0000  -60.0000 196

 11 omega   -7.00   91.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   38.0000   30.0000 196

 12 omega   -3.00   87.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   57.0000 -180.0000 180

 13 omega  -50.00   25.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7723   79.0000  144.0000 150

 14 omega  -51.00   24.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7723   80.0000   44.0000 150

 15 omega   -3.00   57.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2255   57.0000   60.0000 120

 16 omega  -49.00   51.00   0.5000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7723   77.0000  -90.0000 200

;
_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      0.0673087000
_diffrn_orient_matrix_UB_12      -0.0000079000
_diffrn_orient_matrix_UB_13      -0.0244392000
_diffrn_orient_matrix_UB_21      0.0075279000
_diffrn_orient_matrix_UB_22      -0.0492707000
_diffrn_orient_matrix_UB_23      0.0003160000
_diffrn_orient_matrix_UB_31      -0.0571979000
_diffrn_orient_matrix_UB_32      -0.0010024000
_diffrn_orient_matrix_UB_33      -0.0216994000
_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  0.069
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            100957
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.700
_diffrn_reflns_theta_min         3.192
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         18199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0914P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12828
_reflns_number_total             18199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak25_5
_cod_original_cell_volume        2530.14(15)
_cod_database_code               4081433
_audit_block_refno               1405
_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 Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C12(H12), C53(H53), C56(H56), C59(H59), C62(H62)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C15(H15A,H15B), C51(H51A,H51B), C52(H52A,H52B),
 C65(H65A,H65B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C67(H67), C68(H68),
 C69(H69), C70(H70), C71(H71)
2.d Idealised Me refined as rotating group:
 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),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C54(H54A,H54B,H54C), C55(H55A,H55B,
 H55C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,
 H61B,H61C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C),
 C73(H73A,H73B,H73C)
;
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.900
_shelx_res_checksum              75719
_shelxl_version_number           2013-3
_cell_oxdiff_length_a            8.1001(3)
_cell_oxdiff_length_b            14.4306(4)
_cell_oxdiff_length_c            21.9136(8)
_cell_oxdiff_angle_alpha         89.652(3)
_cell_oxdiff_angle_beta          82.032(3)
_cell_oxdiff_angle_gamma         85.869(3)
_cell_oxdiff_volume              2530.13(15)
_cell_oxdiff_measurement_reflns_used 11606
_cell_oxdiff_twin_number         2