metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis{N-[(di­ethyl­amino)­di­methyl­sil­yl]anilinido-κ2N,N′}nickel(II)

aDepartment of Chemistry, Taiyuan Teachers College, Taiyuan 030031, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, People's Republic of China
*Correspondence e-mail: sdbai@sxu.edu.cn

(Received 22 February 2012; accepted 26 February 2012; online 3 March 2012)

The mononuclear NiII amide, [Ni(C12H21N2Si)2], has the NiII atom N,N′-chelated by the N-silylated anilinide ligands. The ligands are arranged cis to each other and obey the C2-symmetry operation. The two ends of the N—Si—N chelating unit exhibit different affinities for the metal atom: the Ni—Nanilinide bond length is 1.913 (3) Å and Ni—Namine is 2.187 (3) Å. The four-coordinate NiII ion demonstrates a distorted tetra­hedral geometry.

Related literature

For related reviews of metal amides, see: Holm et al. (1996[Holm, R. H., Kenneppohl, P. & Solomon, E. I. (1996). Chem. Rev. 96, 2239-2314.]); Kempe (2000[Kempe, R. (2000). Angew. Chem. Int. Ed. 39, 468-493.]). For the catalytic applications of related N-silylated anilinide group 4 metal compounds towards olefin polymerization, see: Gibson et al. (1998[Gibson, V. C., Kimberley, B. S., White, A. J. P., Williams, D. J. & Howard, P. (1998). Chem. Commun. pp. 313-314.]); Hill & Hitchcock (2002[Hill, M. S. & Hitchcock, P. B. (2002). Organometallics, 21, 3258-3262.]); Yuan et al. (2010[Yuan, S. F., Wei, X. H., Tong, H. B., Zhang, L. P., Liu, D. S. & Sun, W. H. (2010). Organometallics, 29, 2085-2092.]); Zai et al. (2010[Zai, S. B., Liu, F. S., Gao, H. Y., Li, C., Zhou, G. Y., Cheng, S., Guo, L. H., Zhang, L., Zhu, F. M. & Wu, Q. (2010). Chem. Commun. 46, 4321-4323.]). For related organometallic compounds with analogous anilinide ligands, see: Schumann et al. (2000[Schumann, H., Gottfriedsen, J., Dechert, S. & Girgsdies, F. (2000). Z. Anorg. Allg. Chem. 626, 747-758.]); Chen (2008[Chen, J. (2008). Acta Cryst. E64, m938.], 2009[Chen, J. (2009). Acta Cryst. E65, m1307.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C12H21N2Si)2]

  • Mr = 501.49

  • Orthorhombic, F d d 2

  • a = 21.2631 (11) Å

  • b = 30.0347 (16) Å

  • c = 8.6228 (5) Å

  • V = 5506.8 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.81 mm−1

  • T = 295 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.823, Tmax = 0.855

  • 6217 measured reflections

  • 2414 independent reflections

  • 2145 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.04

  • 2414 reflections

  • 141 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.20 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1038 Friedel pairs

  • Flack parameter: 0.012 (17)

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Metal amides were important substitutes for cyclopentadienyl derivatives and were found to have valuable applications in various industrial and biological processes (Holm et al., 1996; Kempe, 2000). Group 4 metal amides with the N-silylated anilinide ligands were active catalysts for olefin polymerization (Gibson et al., 1998; Hill & Hitchcock, 2002). Our research interest focused on N-silylated anilinide ligands bearing a pendant amino group. Analogous compounds with different metals including Zn (Schumann et al., 2000), Zr (Chen, 2009) and Fe (Chen, 2008) have been synthesized and the zirconium compounds were reported showing good performance in ethylene polymerization (Yuan et al., 2010). Recently, a kind of bidentate N–donor ligand supported nickel complex activated by MAO was used as a catalyst conducting longstanding living ethylene polymerization (Zai et al., 2010). In view of the importance of these compounds, the synthesis and crystal structure of a new nickel(II) anilinide complex is reported.

The title compound was prepared by one–pot reaction of LiBun, N–[(diethylamino)dimethylsilyl]aniline and NiCl2. It is monomeric and the ligand has an N—Si—N chelating group. It is presumed that the empty d–orbitals on silicon would interact with the lone–pair electrons on the p–orbital of nitrogen center through a d···pπ interaction, resulting in a "quasi" conjugated N—Si—N motif. Compared with rigid N—C—N chelating unit in the amidinate ligand, the N1—Si1—N2 chelating group is much flexible. The Ni center is fixed by two ligands. Each ligand bites the center with an N1—Ni1—N2 angle of 77.82 (11)°. As biting the metal center, the angle of N1—Si1—N2 is constrained to be 95.28 (13)°. The two ends of the N—Si—N chelating unit exhibit different affinities for the metal center. Ni—Nanilinide bond is 1.913 (3) Å and Ni—Namino bond is 2.187 (3)Å. The coordinate geometry of Nanilinide atom is trigonal planar (sum of three angles around it being 359°). Both distances of Si1—N1 (1.699 (3)Å) and N1—C1 (1.375 (4)Å) are short. It suggests a certain degree delocalization of the lone–pair electron density from the p–orbital of N1 to the π–orbital of the phenylsubstituent. The two ligands around the Ni atom are arranged cis to each other and obey the C2 symmetry operation. The four-coordinate Ni atom demonstrates a distorted tetrahedral geometry.

Related literature top

For related reviews of meatal amides, see: Holm et al. (1996); Kempe (2000). For the catalytic applications of related N-silylated analido group 4 metal compounds towards olefin polymerization, see: Gibson et al. (1998); Hill & Hitchcock (2002); Yuan et al. (2010); Zai et al. (2010). For related organometallic compounds with analogous analido ligands, see: Schumann et al. (2000); Chen (2008, 2009).

Experimental top

A solution of LiBun (1.6 M, 1.9 ml, 3.0 mmol) in hexane was slowly added into a solution of N–[(diethylamino)dimethylsilyl]aniline (0.67 g, 3.0 mmol) in THF (20 ml) at 273 K by syringe. The mixture was stirred at room temperature for two hours and then added to a stirring suspension of NiCl2 (0.20 g, 1.5 mmol) in THF (20 ml) at 273 K. The resulting mixture was stirred at room temperature for 8 h. Then all the volatiles were removed under vacuum. The residue was extracted with toluene (25 ml). The filtrate was concentrated to give the title compound as red crystals (yield 0.39 g, 52%). M.p.: 451–452 K. MS (EI, 70 eV): m/z 502 [M]+. Anal. Calc. for C24H42Ni2N4Si2: C, 57.48; H, 8.44; N, 11.17%. Found: C, 56.99; H, 8.13; N, 10.93%.

Refinement top

The methyl H atoms were constrained to an ideal geometry, with C—H distances of 0.96Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C–C and C–Si bonds. The methylene H atoms were constrained with C—H distances of 0.97Å and Uiso(H) = 1.2Ueq(C). The phenyl H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure, showing the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. Symmetry codes: (i) -x+3/2, -y+1/2, z.
Bis{N-[(diethylamino)dimethylsilyl]anilinido- κ2N,N'}nickel(II) top
Crystal data top
[Ni(C12H21N2Si)2]Dx = 1.210 Mg m3
Mr = 501.49Melting point = 451–452 K
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 2035 reflections
a = 21.2631 (11) Åθ = 2.1–26.4°
b = 30.0347 (16) ŵ = 0.81 mm1
c = 8.6228 (5) ÅT = 295 K
V = 5506.8 (5) Å3Block, red
Z = 80.25 × 0.20 × 0.20 mm
F(000) = 2160
Data collection top
Bruker SMART CCD
diffractometer
2414 independent reflections
Radiation source: fine-focus sealed tube2145 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scanθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2522
Tmin = 0.823, Tmax = 0.855k = 3634
6217 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0724P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2414 reflectionsΔρmax = 0.48 e Å3
141 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack (1983), 1038 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.012 (17)
Crystal data top
[Ni(C12H21N2Si)2]V = 5506.8 (5) Å3
Mr = 501.49Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 21.2631 (11) ŵ = 0.81 mm1
b = 30.0347 (16) ÅT = 295 K
c = 8.6228 (5) Å0.25 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
2414 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2145 reflections with I > 2σ(I)
Tmin = 0.823, Tmax = 0.855Rint = 0.029
6217 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104Δρmax = 0.48 e Å3
S = 1.04Δρmin = 0.20 e Å3
2414 reflectionsAbsolute structure: Flack (1983), 1038 Friedel pairs
141 parametersAbsolute structure parameter: 0.012 (17)
1 restraint
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cells.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F2, conventional R–factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F2 are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.75000.25000.59583 (5)0.03740 (17)
Si10.62152 (4)0.24725 (3)0.62421 (11)0.0448 (3)
N10.67563 (11)0.23000 (10)0.4923 (4)0.0430 (6)
N20.67555 (11)0.28051 (8)0.7349 (4)0.0426 (6)
C10.67006 (15)0.20291 (10)0.3645 (4)0.0431 (7)
C20.72350 (19)0.18285 (13)0.2987 (4)0.0564 (9)
H2A0.76290.18890.34050.068*
C30.7188 (2)0.15423 (13)0.1727 (4)0.0622 (10)
H3A0.75500.14130.13180.075*
C40.6615 (2)0.14486 (13)0.1082 (5)0.0700 (11)
H4A0.65850.12550.02440.084*
C50.6092 (2)0.16427 (14)0.1681 (5)0.0663 (11)
H5A0.57020.15850.12330.080*
C60.61285 (17)0.19221 (13)0.2936 (4)0.0567 (9)
H6A0.57600.20450.33300.068*
C70.58850 (18)0.20036 (14)0.7411 (5)0.0668 (11)
H7A0.54350.20260.74340.100*
H7B0.60460.20190.84490.100*
H7C0.60050.17250.69490.100*
C80.55404 (18)0.28164 (14)0.5536 (7)0.0819 (15)
H8A0.51530.26900.59020.123*
H8B0.55400.28210.44230.123*
H8C0.55820.31150.59210.123*
C90.6760 (2)0.27464 (13)0.9052 (5)0.0579 (9)
H9A0.71490.28700.94520.069*
H9B0.67640.24300.92740.069*
C100.6211 (2)0.29574 (18)0.9940 (7)0.0892 (15)
H10A0.62610.29031.10300.134*
H10B0.58220.28290.95920.134*
H10C0.62050.32730.97540.134*
C110.67674 (16)0.32842 (11)0.6879 (5)0.0531 (9)
H11A0.64190.34360.73750.064*
H11B0.67040.33030.57660.064*
C120.73718 (17)0.35238 (12)0.7289 (6)0.0634 (10)
H12A0.73470.38280.69480.095*
H12B0.77190.33790.67870.095*
H12C0.74320.35160.83920.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0262 (3)0.0458 (3)0.0402 (3)0.0003 (2)0.0000.000
Si10.0273 (4)0.0509 (5)0.0561 (8)0.0002 (3)0.0019 (4)0.0001 (4)
N10.0295 (13)0.0548 (16)0.0446 (15)0.0033 (11)0.0011 (12)0.0014 (13)
N20.0320 (13)0.0449 (15)0.0510 (16)0.0044 (10)0.0024 (13)0.0001 (13)
C10.0439 (17)0.0488 (17)0.0365 (18)0.0049 (13)0.0020 (14)0.0065 (14)
C20.0478 (19)0.075 (2)0.046 (2)0.0021 (17)0.0036 (16)0.0034 (17)
C30.073 (3)0.070 (2)0.0439 (19)0.008 (2)0.004 (2)0.0073 (18)
C40.106 (3)0.063 (2)0.0407 (19)0.013 (2)0.009 (2)0.0014 (18)
C50.073 (3)0.075 (3)0.052 (2)0.018 (2)0.012 (2)0.0021 (19)
C60.048 (2)0.066 (2)0.056 (2)0.0136 (16)0.0102 (18)0.0067 (17)
C70.062 (2)0.070 (2)0.068 (3)0.0159 (19)0.021 (2)0.001 (2)
C80.0393 (19)0.080 (3)0.126 (5)0.0105 (18)0.028 (2)0.004 (3)
C90.063 (2)0.059 (2)0.052 (2)0.0005 (17)0.0074 (18)0.0018 (18)
C100.089 (3)0.102 (3)0.077 (3)0.010 (2)0.027 (3)0.012 (3)
C110.0448 (18)0.0486 (19)0.066 (2)0.0059 (14)0.0031 (16)0.0046 (16)
C120.061 (2)0.047 (2)0.082 (3)0.0021 (16)0.010 (2)0.0029 (19)
Geometric parameters (Å, º) top
Ni1—N11.913 (3)C5—C61.372 (6)
Ni1—N1i1.913 (3)C5—H5A0.9300
Ni1—N2i2.187 (3)C6—H6A0.9300
Ni1—N22.187 (3)C7—H7A0.9600
Ni1—Si1i2.7441 (8)C7—H7B0.9600
Ni1—Si12.7441 (8)C7—H7C0.9600
Si1—N11.699 (3)C8—H8A0.9600
Si1—N21.797 (3)C8—H8B0.9600
Si1—C71.869 (4)C8—H8C0.9600
Si1—C81.870 (4)C9—C101.534 (6)
N1—C11.375 (4)C9—H9A0.9700
N2—C91.479 (5)C9—H9B0.9700
N2—C111.495 (4)C10—H10A0.9600
C1—C61.399 (5)C10—H10B0.9600
C1—C21.406 (5)C10—H10C0.9600
C2—C31.389 (5)C11—C121.515 (5)
C2—H2A0.9300C11—H11A0.9700
C3—C41.369 (6)C11—H11B0.9700
C3—H3A0.9300C12—H12A0.9600
C4—C51.359 (6)C12—H12B0.9600
C4—H4A0.9300C12—H12C0.9600
N1—Ni1—N1i124.35 (18)C3—C4—H4A120.4
N1—Ni1—N2i136.28 (10)C4—C5—C6121.0 (4)
N1i—Ni1—N2i77.82 (11)C4—C5—H5A119.5
N1—Ni1—N277.82 (11)C6—C5—H5A119.5
N1i—Ni1—N2136.28 (10)C5—C6—C1122.3 (4)
N2i—Ni1—N2113.51 (15)C5—C6—H6A118.8
N1—Ni1—Si1i150.95 (9)C1—C6—H6A118.8
N1i—Ni1—Si1i37.73 (9)Si1—C7—H7A109.5
N2i—Ni1—Si1i40.81 (7)Si1—C7—H7B109.5
N2—Ni1—Si1i131.23 (8)H7A—C7—H7B109.5
N1—Ni1—Si137.73 (9)Si1—C7—H7C109.5
N1i—Ni1—Si1150.95 (9)H7A—C7—H7C109.5
N2i—Ni1—Si1131.23 (8)H7B—C7—H7C109.5
N2—Ni1—Si140.81 (7)Si1—C8—H8A109.5
Si1i—Ni1—Si1169.77 (4)Si1—C8—H8B109.5
N1—Si1—N295.28 (13)H8A—C8—H8B109.5
N1—Si1—C7112.69 (18)Si1—C8—H8C109.5
N2—Si1—C7111.89 (18)H8A—C8—H8C109.5
N1—Si1—C8118.0 (2)H8B—C8—H8C109.5
N2—Si1—C8110.88 (17)N2—C9—C10116.2 (4)
C7—Si1—C8107.7 (2)N2—C9—H9A108.2
C7—Si1—Ni1116.41 (13)C10—C9—H9A108.2
C8—Si1—Ni1135.91 (16)N2—C9—H9B108.2
C1—N1—Si1131.2 (2)C10—C9—H9B108.2
C1—N1—Ni1129.1 (2)H9A—C9—H9B107.4
Si1—N1—Ni198.73 (15)C9—C10—H10A109.5
C9—N2—C11112.6 (3)C9—C10—H10B109.5
C9—N2—Si1117.7 (2)H10A—C10—H10B109.5
C11—N2—Si1113.7 (2)C9—C10—H10C109.5
C9—N2—Ni1119.3 (2)H10A—C10—H10C109.5
C11—N2—Ni1104.02 (19)H10B—C10—H10C109.5
Si1—N2—Ni186.48 (12)N2—C11—C12114.1 (3)
N1—C1—C6124.1 (3)N2—C11—H11A108.7
N1—C1—C2120.5 (3)C12—C11—H11A108.7
C6—C1—C2115.4 (3)N2—C11—H11B108.7
C3—C2—C1121.5 (4)C12—C11—H11B108.7
C3—C2—H2A119.2H11A—C11—H11B107.6
C1—C2—H2A119.2C11—C12—H12A109.5
C4—C3—C2120.6 (4)C11—C12—H12B109.5
C4—C3—H3A119.7H12A—C12—H12B109.5
C2—C3—H3A119.7C11—C12—H12C109.5
C5—C4—C3119.1 (4)H12A—C12—H12C109.5
C5—C4—H4A120.4H12B—C12—H12C109.5
Symmetry code: (i) x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Ni(C12H21N2Si)2]
Mr501.49
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)295
a, b, c (Å)21.2631 (11), 30.0347 (16), 8.6228 (5)
V3)5506.8 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.81
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.823, 0.855
No. of measured, independent and
observed [I > 2σ(I)] reflections
6217, 2414, 2145
Rint0.029
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.104, 1.04
No. of reflections2414
No. of parameters141
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.20
Absolute structureFlack (1983), 1038 Friedel pairs
Absolute structure parameter0.012 (17)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was performed under the sponsorship of the Natural Science Foundation of China (20702029) and the Natural Science Foundation of Shanxi Province (2008011024).

References

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