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_4081431
_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         'C19 H37 Cl2 N Ni P2 S'
_chemical_formula_sum            'C19 H37 Cl2 N Ni P2 S'
_chemical_formula_weight         503.10
_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_ak17
_audit_creation_date             2013-07-04
_audit_update_record             'Thu Jul  4 09:04:12 CEST 2013'
_cell_angle_alpha                90
_cell_angle_beta                 107.380(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.030(5)
_cell_length_b                   15.352(9)
_cell_length_c                   14.824(8)
_cell_measurement_reflns_used    8084
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.35
_cell_volume                     2396(2)
_computing_cell_refinement
;
SAINT 8.x (Bruker AXS, 1997-2012). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT 8.x (Bruker AXS, 1997-2011)'
_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_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            58581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.125
_diffrn_reflns_theta_min         1.958
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.8708
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         8026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0453P)^2^+2.3691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6250
_reflns_number_total             8026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak17
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4081431
_audit_block_refno               1190
_audit_block_usercomment         AK201
_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 Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19)
2.b 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)
;
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.843
_shelx_res_checksum              60691
_shelxl_version_number           2013-3