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_4081434
_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_sum            'C21 H50 Cl N Ni P2 Si'
_chemical_formula_weight         500.81
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ak29
_audit_creation_date
;
'Tue May 15 11:35:23 2012'
;
_audit_creation_method           SHELXL-2013
_audit_update_record             'Fri Apr  5 17:35:34 CEST 2013'
_cell_angle_alpha                70.6889(10)
_cell_angle_beta                 87.1736(8)
_cell_angle_gamma                88.1818(8)
_cell_formula_units_Z            4
_cell_length_a                   11.09533(9)
_cell_length_b                   15.85188(18)
_cell_length_c                   16.66637(18)
_cell_measurement_reflns_used    83451
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      32.1822
_cell_measurement_theta_min      3.1228
_cell_volume                     2762.65(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_publication_material
'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2011 (Giacovazzo et al., 2011)'
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 phi      1.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
  28.7629   28.7629  -20.0000     -     76

  2 phi    240.00  359.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
  28.7629   28.7629  -40.0000     -     119

  3 omega   15.00  105.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   19.0000   60.0000 90

  4 omega   17.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000   30.0000 27

  5 omega   -1.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   38.0000 -150.0000 90

  6 omega    1.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   77.0000 -150.0000 87

  7 phi    121.00  211.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   28.7629    0.0000     -     90

  8 omega   -5.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   80.0000  -46.0000 28

  9 omega    5.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000  120.0000 41

 10 omega   -2.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   38.0000  -30.0000 57

 11 omega   -6.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   80.0000   74.0000 29

 12 omega    5.00   52.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000   60.0000 47

 13 omega   -5.00   23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   78.0000  165.0000 28

 14 omega    6.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000    0.0000 45

 15 omega   -6.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   30.0000 49

 16 omega  -61.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   30.0000 25

 17 omega  -61.00    6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   90.0000 67

 18 omega  -62.00  -19.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000  -30.0000 43

 19 omega  -62.00  -36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000 -180.0000 26

 20 omega  -21.00    6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   54.0000 27

 21 omega  -48.00    1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   57.0000 -150.0000 49

 22 omega  -57.00  -10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000  -90.0000 47

 23 omega  -61.00  -23.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   54.0000 38

 24 omega  -64.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   80.0000 -139.0000 59

 25 omega  -63.00  -18.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   80.0000  129.0000 45

 26 omega    5.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000   30.0000 94

 27 omega    5.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000    0.0000 94

 28 omega   -3.00  102.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   38.0000  -30.0000 105

 29 omega    5.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000  -90.0000 94

 30 omega   -3.00  102.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   38.0000  150.0000 105

 31 omega    5.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000 -150.0000 94

 32 omega   -5.00   28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   78.0000  165.0000 33

 33 omega   -6.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   80.0000  -46.0000 30

 34 omega   -6.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   80.0000   74.0000 30

 35 omega    5.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   57.0000  -60.0000 94

 36 omega   -4.00  101.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629   77.0000   60.0000 105

 37 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000  150.0000 105

 38 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000  -60.0000 105

 39 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   90.0000 105

 40 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   30.0000 105

 41 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000 -180.0000 105

 42 omega  -53.00   41.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   57.0000  -60.0000 94

 43 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000  -30.0000 105

 44 omega  -64.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   80.0000  129.0000 88

 45 omega  -64.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   80.0000 -139.0000 88

 46 omega  -46.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629    0.0000  120.0000 150

 47 omega  -46.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629    0.0000    0.0000 150

 48 phi    120.00  240.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   28.7629    0.0000     -     120

 49 omega  -46.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.7629    0.0000  240.0000 150

 50 omega -104.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317    0.0000    0.0000 150

 51 omega -104.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317    0.0000  120.0000 150

 52 omega -104.00  -79.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317    0.0000  240.0000 25

 53 omega  -62.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -29.2317   77.0000   54.0000 105

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      0.0123559000
_diffrn_orient_matrix_UB_12      -0.0309076000
_diffrn_orient_matrix_UB_13      -0.0220134000
_diffrn_orient_matrix_UB_21      -0.0323949000
_diffrn_orient_matrix_UB_22      -0.0332035000
_diffrn_orient_matrix_UB_23      0.0324352000
_diffrn_orient_matrix_UB_31      -0.0538119000
_diffrn_orient_matrix_UB_32      0.0138148000
_diffrn_orient_matrix_UB_33      -0.0223712000
_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  0.0560
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            259761
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.255
_diffrn_reflns_theta_min         3.129
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.966
_exptl_absorpt_correction_T_max  1.425
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.3243
_exptl_crystal_size_mid          0.2015
_exptl_crystal_size_min          0.1497
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         19024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+1.3400P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18015
_reflns_number_total             19024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak29
_cod_database_code               4081434
_audit_block_refno               1499
_audit_block_usercomment         'AK390 plate orange'
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.910
_shelxl_version_number           2013-2
_shelx_res_checksum              7235
_cell_oxdiff_length_a            11.09533(9)
_cell_oxdiff_length_b            15.85188(18)
_cell_oxdiff_length_c            16.66637(18)
_cell_oxdiff_angle_alpha         70.6889(10)
_cell_oxdiff_angle_beta          87.1736(8)
_cell_oxdiff_angle_gamma         88.1818(8)
_cell_oxdiff_volume              2762.65(5)
_cell_oxdiff_measurement_reflns_used 83451
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_theta     30.44
_reflns_odcompleteness_iscentric 1