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_4081429
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H35 Cl2 N Ni P2, 0.5(C2 H4 Cl4)'
_chemical_formula_sum            'C16 H37 Cl4 N Ni P2'
_chemical_formula_weight         505.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      8
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_space_group_name_H-M   'C 1 m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ak44b
_audit_creation_date
;
'Tue Nov 27 11:28:11 2012'
;
_audit_update_record             'Wed Jul  3 11:49:51 CEST 2013'
_cell_angle_alpha                90
_cell_angle_beta                 104.1087(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.45240(7)
_cell_length_b                   14.56303(8)
_cell_length_c                   7.24125(4)
_cell_measurement_reflns_used    35903
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      32.3120
_cell_measurement_theta_min      3.3313
_cell_volume                     1171.277(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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)'
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_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            'Agilent EOS'
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_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -43.00   56.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000    0.0000 198

  2 omega  -44.00   59.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -80.0000  168.7748 206

  3 omega    3.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   90.0000 188

  4 omega    6.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000 -150.0000 180

  5 omega   -3.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000  -90.0000 200

  6 omega  -43.00   54.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000   90.0000 194

  7 omega   -1.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000    0.0000 196

  8 omega  -44.00   59.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -80.0000  -99.8871 206

  9 omega  -48.00   -2.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.0224  -38.0000   60.0000 92

 10 omega  -42.00   48.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000   60.0000 180

 11 omega  -42.00   48.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -57.0000 -120.0000 180

 12 omega   -3.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -150.0000 200

 13 omega    6.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000  -60.0000 180

 14 omega  -43.00   57.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000  -30.0000 200

 15 omega    6.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000  120.0000 180

 16 omega    6.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000   30.0000 180

 17 omega  -43.00   57.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000 -150.0000 200

 18 omega  -43.00   57.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000   90.0000 200

 19 omega    1.00   99.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   38.0000  -60.0000 196

 20 omega   -3.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000   60.0000 200

 21 omega  -43.00   57.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662  -77.0000   16.7884 200

 22 omega   -3.00   97.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   77.0000 -120.0000 200

 23 omega  -59.00   24.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.0224   80.0000  -69.8629 166

 24 omega    6.00   96.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662   57.0000 -180.0000 180

 25 omega  -46.00  100.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662    0.0000  120.0000 292

 26 omega  -46.00  100.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662    0.0000  240.0000 292

 27 omega  -46.00  100.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8662    0.0000    0.0000 292

 28 omega -100.00  -14.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.0224    0.0000    0.0000 172

;
_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      -0.0607927000
_diffrn_orient_matrix_UB_12      -0.0115982000
_diffrn_orient_matrix_UB_13      -0.0421565000
_diffrn_orient_matrix_UB_21      0.0175613000
_diffrn_orient_matrix_UB_22      -0.0192230000
_diffrn_orient_matrix_UB_23      -0.0790998000
_diffrn_orient_matrix_UB_31      0.0085092000
_diffrn_orient_matrix_UB_32      -0.0432348000
_diffrn_orient_matrix_UB_33      0.0465272000
_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  0.0188
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            41451
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.385
_diffrn_reflns_theta_min         3.338
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       irregular
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.3009
_exptl_crystal_size_mid          0.2020
_exptl_crystal_size_min          0.1903
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.001(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0148
_refine_ls_R_factor_gt           0.0147
_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^)+(0.0183P)^2^+0.4659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0367
_refine_ls_wR_factor_ref         0.0367
_reflns_Friedel_coverage         0.969
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4179
_reflns_number_total             4200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak44b
_cod_original_cell_volume        1171.278(12)
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               4081429
_audit_block_refno               1647
_audit_block_usercomment         AK578
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H21A,H21B} of C21, {H1A,H1B} of C1
 At 1.5 times of:
  All C(H,H,H) groups, {H15A,H15B} of C15
2. Others
 Fixed Sof: H21A(0.5) H21B(0.5)
3.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)
;
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.871
_shelx_hkl_checksum              1703
_cell_oxdiff_length_a            11.45376(10)
_cell_oxdiff_length_b            14.55979(10)
_cell_oxdiff_length_c            7.24139(5)
_cell_oxdiff_angle_alpha         89.9763(6)
_cell_oxdiff_angle_beta          104.0891(7)
_cell_oxdiff_angle_gamma         89.9988(6)
_cell_oxdiff_volume              1171.278(16)
_cell_oxdiff_measurement_reflns_used 35903
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_theta     30.44
_reflns_odcompleteness_iscentric 1