Bis{N-[(diethyl-amino)-dimethyl-sil-yl]anilinido-κ(2)N,N'}nickel(II).

The mononuclear Ni(II) amide, [Ni(C(12)H(21)N(2)Si)(2)], has the Ni(II) atom N,N'-chelated by the N-silylated anilinide ligands. The ligands are arranged cis to each other and obey the C(2)-symmetry operation. The two ends of the N-Si-N chelating unit exhibit different affinities for the metal atom: the Ni-N(anilinide) bond length is 1.913 (3) Å and Ni-N(amine) is 2.187 (3) Å. The four-coordinate Ni(II) ion demonstrates a distorted tetra-hedral geometry.

Related literature

For related reviews of metal amides, see: Holm et al. (1996 ▶); Kempe (2000 ▶). For the catalytic applications of related N-silylated anilinide 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 anilinide ligands, see: Schumann et al. (2000 ▶); Chen (2008 ▶, 2009 ▶).

Experimental

Crystal data

[Ni(C12H21N2Si)2]

M = 501.49

Orthorhombic,

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 ▶) T min = 0.823, T max = 0.855

6217 measured reflections

2414 independent reflections

2145 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 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 ▶), 1038 Friedel pairs

Flack parameter: 0.012 (17)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008550/rk2340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008550/rk2340Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C12H21N2Si)2]	Dx = 1.210 Mg m−3
Mr = 501.49	Melting point = 451–452 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 2035 reflections
a = 21.2631 (11) Å	θ = 2.1–26.4°
b = 30.0347 (16) Å	µ = 0.81 mm−1
c = 8.6228 (5) Å	T = 295 K
V = 5506.8 (5) Å3	Block, red
Z = 8	0.25 × 0.20 × 0.20 mm
F(000) = 2160

Bruker SMART CCD diffractometer	2414 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scan	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→22
Tmin = 0.823, Tmax = 0.855	k = −36→34
6217 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-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 reflections	Δρmax = 0.48 e Å−3
141 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 1038 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (17)

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.

	x	y	z	Uiso*/Ueq
Ni1	0.7500	0.2500	0.59583 (5)	0.03740 (17)
Si1	0.62152 (4)	0.24725 (3)	0.62421 (11)	0.0448 (3)
N1	0.67563 (11)	0.23000 (10)	0.4923 (4)	0.0430 (6)
N2	0.67555 (11)	0.28051 (8)	0.7349 (4)	0.0426 (6)
C1	0.67006 (15)	0.20291 (10)	0.3645 (4)	0.0431 (7)
C2	0.72350 (19)	0.18285 (13)	0.2987 (4)	0.0564 (9)
H2A	0.7629	0.1889	0.3405	0.068*
C3	0.7188 (2)	0.15423 (13)	0.1727 (4)	0.0622 (10)
H3A	0.7550	0.1413	0.1318	0.075*
C4	0.6615 (2)	0.14486 (13)	0.1082 (5)	0.0700 (11)
H4A	0.6585	0.1255	0.0244	0.084*
C5	0.6092 (2)	0.16427 (14)	0.1681 (5)	0.0663 (11)
H5A	0.5702	0.1585	0.1233	0.080*
C6	0.61285 (17)	0.19221 (13)	0.2936 (4)	0.0567 (9)
H6A	0.5760	0.2045	0.3330	0.068*
C7	0.58850 (18)	0.20036 (14)	0.7411 (5)	0.0668 (11)
H7A	0.5435	0.2026	0.7434	0.100*
H7B	0.6046	0.2019	0.8449	0.100*
H7C	0.6005	0.1725	0.6949	0.100*
C8	0.55404 (18)	0.28164 (14)	0.5536 (7)	0.0819 (15)
H8A	0.5153	0.2690	0.5902	0.123*
H8B	0.5540	0.2821	0.4423	0.123*
H8C	0.5582	0.3115	0.5921	0.123*
C9	0.6760 (2)	0.27464 (13)	0.9052 (5)	0.0579 (9)
H9A	0.7149	0.2870	0.9452	0.069*
H9B	0.6764	0.2430	0.9274	0.069*
C10	0.6211 (2)	0.29574 (18)	0.9940 (7)	0.0892 (15)
H10A	0.6261	0.2903	1.1030	0.134*
H10B	0.5822	0.2829	0.9592	0.134*
H10C	0.6205	0.3273	0.9754	0.134*
C11	0.67674 (16)	0.32842 (11)	0.6879 (5)	0.0531 (9)
H11A	0.6419	0.3436	0.7375	0.064*
H11B	0.6704	0.3303	0.5766	0.064*
C12	0.73718 (17)	0.35238 (12)	0.7289 (6)	0.0634 (10)
H12A	0.7347	0.3828	0.6948	0.095*
H12B	0.7719	0.3379	0.6787	0.095*
H12C	0.7432	0.3516	0.8392	0.095*

	U11	U22	U33	U12	U13	U23
Ni1	0.0262 (3)	0.0458 (3)	0.0402 (3)	−0.0003 (2)	0.000	0.000
Si1	0.0273 (4)	0.0509 (5)	0.0561 (8)	0.0002 (3)	0.0019 (4)	−0.0001 (4)
N1	0.0295 (13)	0.0548 (16)	0.0446 (15)	−0.0033 (11)	−0.0011 (12)	0.0014 (13)
N2	0.0320 (13)	0.0449 (15)	0.0510 (16)	0.0044 (10)	0.0024 (13)	0.0001 (13)
C1	0.0439 (17)	0.0488 (17)	0.0365 (18)	−0.0049 (13)	−0.0020 (14)	0.0065 (14)
C2	0.0478 (19)	0.075 (2)	0.046 (2)	−0.0021 (17)	−0.0036 (16)	−0.0034 (17)
C3	0.073 (3)	0.070 (2)	0.0439 (19)	0.008 (2)	0.004 (2)	−0.0073 (18)
C4	0.106 (3)	0.063 (2)	0.0407 (19)	−0.013 (2)	−0.009 (2)	−0.0014 (18)
C5	0.073 (3)	0.075 (3)	0.052 (2)	−0.018 (2)	−0.012 (2)	0.0021 (19)
C6	0.048 (2)	0.066 (2)	0.056 (2)	−0.0136 (16)	−0.0102 (18)	0.0067 (17)
C7	0.062 (2)	0.070 (2)	0.068 (3)	−0.0159 (19)	0.021 (2)	0.001 (2)
C8	0.0393 (19)	0.080 (3)	0.126 (5)	0.0105 (18)	−0.028 (2)	0.004 (3)
C9	0.063 (2)	0.059 (2)	0.052 (2)	0.0005 (17)	0.0074 (18)	−0.0018 (18)
C10	0.089 (3)	0.102 (3)	0.077 (3)	0.010 (2)	0.027 (3)	−0.012 (3)
C11	0.0448 (18)	0.0486 (19)	0.066 (2)	0.0059 (14)	0.0031 (16)	−0.0046 (16)
C12	0.061 (2)	0.047 (2)	0.082 (3)	−0.0021 (16)	−0.010 (2)	−0.0029 (19)

Ni1—N1	1.913 (3)	C5—C6	1.372 (6)
Ni1—N1i	1.913 (3)	C5—H5A	0.9300
Ni1—N2i	2.187 (3)	C6—H6A	0.9300
Ni1—N2	2.187 (3)	C7—H7A	0.9600
Ni1—Si1i	2.7441 (8)	C7—H7B	0.9600
Ni1—Si1	2.7441 (8)	C7—H7C	0.9600
Si1—N1	1.699 (3)	C8—H8A	0.9600
Si1—N2	1.797 (3)	C8—H8B	0.9600
Si1—C7	1.869 (4)	C8—H8C	0.9600
Si1—C8	1.870 (4)	C9—C10	1.534 (6)
N1—C1	1.375 (4)	C9—H9A	0.9700
N2—C9	1.479 (5)	C9—H9B	0.9700
N2—C11	1.495 (4)	C10—H10A	0.9600
C1—C6	1.399 (5)	C10—H10B	0.9600
C1—C2	1.406 (5)	C10—H10C	0.9600
C2—C3	1.389 (5)	C11—C12	1.515 (5)
C2—H2A	0.9300	C11—H11A	0.9700
C3—C4	1.369 (6)	C11—H11B	0.9700
C3—H3A	0.9300	C12—H12A	0.9600
C4—C5	1.359 (6)	C12—H12B	0.9600
C4—H4A	0.9300	C12—H12C	0.9600
N1—Ni1—N1i	124.35 (18)	C3—C4—H4A	120.4
N1—Ni1—N2i	136.28 (10)	C4—C5—C6	121.0 (4)
N1i—Ni1—N2i	77.82 (11)	C4—C5—H5A	119.5
N1—Ni1—N2	77.82 (11)	C6—C5—H5A	119.5
N1i—Ni1—N2	136.28 (10)	C5—C6—C1	122.3 (4)
N2i—Ni1—N2	113.51 (15)	C5—C6—H6A	118.8
N1—Ni1—Si1i	150.95 (9)	C1—C6—H6A	118.8
N1i—Ni1—Si1i	37.73 (9)	Si1—C7—H7A	109.5
N2i—Ni1—Si1i	40.81 (7)	Si1—C7—H7B	109.5
N2—Ni1—Si1i	131.23 (8)	H7A—C7—H7B	109.5
N1—Ni1—Si1	37.73 (9)	Si1—C7—H7C	109.5
N1i—Ni1—Si1	150.95 (9)	H7A—C7—H7C	109.5
N2i—Ni1—Si1	131.23 (8)	H7B—C7—H7C	109.5
N2—Ni1—Si1	40.81 (7)	Si1—C8—H8A	109.5
Si1i—Ni1—Si1	169.77 (4)	Si1—C8—H8B	109.5
N1—Si1—N2	95.28 (13)	H8A—C8—H8B	109.5
N1—Si1—C7	112.69 (18)	Si1—C8—H8C	109.5
N2—Si1—C7	111.89 (18)	H8A—C8—H8C	109.5
N1—Si1—C8	118.0 (2)	H8B—C8—H8C	109.5
N2—Si1—C8	110.88 (17)	N2—C9—C10	116.2 (4)
C7—Si1—C8	107.7 (2)	N2—C9—H9A	108.2
C7—Si1—Ni1	116.41 (13)	C10—C9—H9A	108.2
C8—Si1—Ni1	135.91 (16)	N2—C9—H9B	108.2
C1—N1—Si1	131.2 (2)	C10—C9—H9B	108.2
C1—N1—Ni1	129.1 (2)	H9A—C9—H9B	107.4
Si1—N1—Ni1	98.73 (15)	C9—C10—H10A	109.5
C9—N2—C11	112.6 (3)	C9—C10—H10B	109.5
C9—N2—Si1	117.7 (2)	H10A—C10—H10B	109.5
C11—N2—Si1	113.7 (2)	C9—C10—H10C	109.5
C9—N2—Ni1	119.3 (2)	H10A—C10—H10C	109.5
C11—N2—Ni1	104.02 (19)	H10B—C10—H10C	109.5
Si1—N2—Ni1	86.48 (12)	N2—C11—C12	114.1 (3)
N1—C1—C6	124.1 (3)	N2—C11—H11A	108.7
N1—C1—C2	120.5 (3)	C12—C11—H11A	108.7
C6—C1—C2	115.4 (3)	N2—C11—H11B	108.7
C3—C2—C1	121.5 (4)	C12—C11—H11B	108.7
C3—C2—H2A	119.2	H11A—C11—H11B	107.6
C1—C2—H2A	119.2	C11—C12—H12A	109.5
C4—C3—C2	120.6 (4)	C11—C12—H12B	109.5
C4—C3—H3A	119.7	H12A—C12—H12B	109.5
C2—C3—H3A	119.7	C11—C12—H12C	109.5
C5—C4—C3	119.1 (4)	H12A—C12—H12C	109.5
C5—C4—H4A	120.4	H12B—C12—H12C	109.5