[1,2-Bis-(diisopropyl-phosphan-yl)ethane-κP,P']dichloridonickel(II).

In the crystal structure of title compound, [NiCl(2)(C(14)H(32)P(2))], the Ni(II) atom lies on a twofold rotation axis and shows a slightly distorted square-planar coordination geometry, with a dihedral angle of 10.01 (8)° between the cis-Cl-Ni-Cl and cis-P-Ni-P planes. There is no significant inter-molecular inter-action except very weak C-H⋯Cl inter-actions. The crystal studied was a racemic twin.

Related literature

For the synthesis, see: Scott et al. (1990 ▶). For applications of nickel complexes to catalytic systems, see: Vicic & Jones (1997 ▶); Arévalo & García (2010 ▶). For related structures, see: Cañavera-Buelvas et al. (2011 ▶); Angulo et al. (2003 ▶); Dahlenburg & Kurth (2001 ▶).

Experimental

Crystal data

[NiCl2(C14H32P2)]

M = 391.95

Tetragonal,

a = 14.2402 (2) Å

c = 18.4369 (7) Å

V = 3738.70 (16) Å3

Z = 8

Mo Kα radiation

μ = 1.48 mm−1

T = 122 K

0.17 × 0.14 × 0.07 mm

Data collection

Oxford Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.975, T max = 0.989

5823 measured reflections

1850 independent reflections

1547 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.070

S = 0.97

1850 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 832 Friedel pairs

Flack parameter: 0.53 (3)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811021209/is2724sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021209/is2724Isup2.hkl

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

[NiCl2(C14H32P2)]	Dx = 1.393 Mg m−3
Mr = 391.95	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4c2	Cell parameters from 3046 reflections
a = 14.2402 (2) Å	θ = 3.4–26.0°
c = 18.4369 (7) Å	µ = 1.48 mm−1
V = 3738.70 (16) Å3	T = 122 K
Z = 8	Prism, brown
F(000) = 1664	0.17 × 0.14 × 0.07 mm

Oxford Xcalibur Atlas Gemini diffractometer	1850 independent reflections
graphite	1547 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.030
ω scans	θmax = 26.1°, θmin = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	h = −16→17
Tmin = 0.975, Tmax = 0.989	k = −17→17
5823 measured reflections	l = −22→16

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
1850 reflections	Δρmax = 0.80 e Å−3
92 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 832 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.53 (3)

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 cell s.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 > 2σ(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
C1	0.5579 (3)	0.2802 (2)	0.4018 (2)	0.0423 (9)
H1	0.5088	0.2434	0.3754	0.051*
C2	0.5856 (3)	0.3616 (3)	0.3527 (3)	0.0708 (15)
H2A	0.5296	0.3982	0.3403	0.106*
H2B	0.6144	0.3371	0.3083	0.106*
H2C	0.6307	0.4019	0.3781	0.106*
C3	0.5142 (3)	0.3145 (3)	0.4703 (2)	0.0580 (13)
H3A	0.5614	0.3477	0.4993	0.087*
H3B	0.49	0.261	0.498	0.087*
H3C	0.4625	0.3573	0.4588	0.087*
C4	0.7002 (3)	0.1639 (3)	0.33272 (17)	0.0457 (10)
H4	0.7238	0.2221	0.3086	0.055*
C5	0.6214 (3)	0.1240 (3)	0.2847 (2)	0.0676 (12)
H5A	0.6454	0.1136	0.2355	0.101*
H5B	0.569	0.1686	0.283	0.101*
H5C	0.5995	0.0642	0.3049	0.101*
C6	0.7832 (3)	0.0972 (3)	0.3400 (2)	0.0554 (12)
H6A	0.7648	0.043	0.3695	0.083*
H6B	0.8356	0.1299	0.3634	0.083*
H6C	0.8025	0.0757	0.2918	0.083*
C7	0.5952 (2)	0.0942 (2)	0.45870 (15)	0.0292 (6)
H7A	0.5299	0.0924	0.4404	0.035*
H7B	0.6277	0.0369	0.4416	0.035*
P1	0.65506 (6)	0.19836 (6)	0.42220 (5)	0.0280 (2)
Cl1	0.83890 (6)	0.31965 (6)	0.58688 (5)	0.0349 (2)
Ni1	0.75392 (2)	0.25392 (2)	0.5	0.02082 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0335 (19)	0.0391 (19)	0.054 (3)	−0.0022 (16)	−0.0121 (19)	0.0064 (18)
C2	0.053 (3)	0.060 (3)	0.099 (4)	0.003 (2)	−0.009 (3)	0.038 (3)
C3	0.039 (2)	0.050 (2)	0.085 (4)	0.0139 (18)	−0.001 (2)	−0.006 (2)
C4	0.064 (3)	0.046 (2)	0.0270 (18)	−0.019 (2)	0.0057 (17)	−0.0057 (17)
C5	0.090 (4)	0.074 (4)	0.039 (2)	−0.015 (2)	−0.013 (2)	−0.016 (2)
C6	0.067 (3)	0.042 (2)	0.057 (3)	−0.004 (2)	0.022 (2)	−0.013 (2)
C7	0.0251 (18)	0.0270 (19)	0.0355 (16)	−0.0077 (12)	−0.0012 (17)	−0.0046 (17)
P1	0.0269 (4)	0.0268 (4)	0.0303 (5)	−0.0055 (3)	−0.0020 (4)	0.0005 (4)
Cl1	0.0306 (4)	0.0344 (5)	0.0397 (5)	−0.0094 (3)	−0.0042 (4)	−0.0077 (4)
Ni1	0.01688 (15)	0.01688 (15)	0.0287 (3)	−0.00262 (17)	0.00055 (18)	−0.00055 (18)

C1—C3	1.491 (5)	C5—H5A	0.98
C1—C2	1.522 (6)	C5—H5B	0.98
C1—P1	1.847 (3)	C5—H5C	0.98
C1—H1	1.00	C6—H6A	0.98
C2—H2A	0.98	C6—H6B	0.98
C2—H2B	0.98	C6—H6C	0.98
C2—H2C	0.98	C7—C7i	1.523 (6)
C3—H3A	0.98	C7—P1	1.838 (3)
C3—H3B	0.98	C7—H7A	0.99
C3—H3C	0.98	C7—H7B	0.99
C4—C6	1.522 (6)	P1—Ni1	2.1600 (9)
C4—C5	1.538 (5)	Cl1—Ni1	2.2150 (8)
C4—P1	1.837 (3)	Ni1—P1i	2.1600 (9)
C4—H4	1.00	Ni1—Cl1i	2.2150 (8)
C3—C1—C2	111.2 (3)	C4—C5—H5C	109.5
C3—C1—P1	110.3 (3)	H5A—C5—H5C	109.5
C2—C1—P1	114.0 (3)	H5B—C5—H5C	109.5
C3—C1—H1	107	C4—C6—H6A	109.5
C2—C1—H1	107	C4—C6—H6B	109.5
P1—C1—H1	107	H6A—C6—H6B	109.5
C1—C2—H2A	109.5	C4—C6—H6C	109.5
C1—C2—H2B	109.5	H6A—C6—H6C	109.5
H2A—C2—H2B	109.5	H6B—C6—H6C	109.5
C1—C2—H2C	109.5	C7i—C7—P1	111.27 (13)
H2A—C2—H2C	109.5	C7i—C7—H7A	109.4
H2B—C2—H2C	109.5	P1—C7—H7A	109.4
C1—C3—H3A	109.5	C7i—C7—H7B	109.4
C1—C3—H3B	109.5	P1—C7—H7B	109.4
H3A—C3—H3B	109.5	H7A—C7—H7B	108
C1—C3—H3C	109.5	C4—P1—C7	105.97 (15)
H3A—C3—H3C	109.5	C4—P1—C1	104.33 (18)
H3B—C3—H3C	109.5	C7—P1—C1	103.68 (17)
C6—C4—C5	112.7 (4)	C4—P1—Ni1	117.79 (14)
C6—C4—P1	111.0 (3)	C7—P1—Ni1	110.76 (10)
C5—C4—P1	111.1 (3)	C1—P1—Ni1	113.10 (12)
C6—C4—H4	107.2	P1—Ni1—P1i	87.91 (5)
C5—C4—H4	107.2	P1—Ni1—Cl1	172.36 (3)
P1—C4—H4	107.2	P1i—Ni1—Cl1	89.73 (3)
C4—C5—H5A	109.5	P1—Ni1—Cl1i	89.73 (3)
C4—C5—H5B	109.5	P1i—Ni1—Cl1i	172.36 (3)
H5A—C5—H5B	109.5	Cl1—Ni1—Cl1i	93.51 (5)
C6—C4—P1—C7	−72.2 (3)	C2—C1—P1—C7	−164.7 (3)
C5—C4—P1—C7	54.2 (3)	C3—C1—P1—Ni1	−50.7 (3)
C6—C4—P1—C1	178.8 (3)	C2—C1—P1—Ni1	75.3 (3)
C5—C4—P1—C1	−54.9 (3)	C4—P1—Ni1—P1i	−129.91 (14)
C6—C4—P1—Ni1	52.4 (3)	C7—P1—Ni1—P1i	−7.74 (12)
C5—C4—P1—Ni1	178.8 (3)	C1—P1—Ni1—P1i	108.15 (14)
C7i—C7—P1—C4	153.8 (3)	C4—P1—Ni1—Cl1	158.0 (3)
C7i—C7—P1—C1	−96.6 (4)	C7—P1—Ni1—Cl1	−79.9 (3)
C7i—C7—P1—Ni1	25.0 (4)	C1—P1—Ni1—Cl1	36.0 (3)
C3—C1—P1—C4	−179.9 (3)	C4—P1—Ni1—Cl1i	42.82 (14)
C2—C1—P1—C4	−53.9 (4)	C7—P1—Ni1—Cl1i	164.99 (13)
C3—C1—P1—C7	69.4 (3)	C1—P1—Ni1—Cl1i	−79.12 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···Cl1ii	0.98	2.94	3.808 (4)	148
C5—H5A···Cl1iii	0.98	2.91	3.777 (4)	148

Table 1

Selected bond lengths (Å)

Ni1—P1	2.1600 (9)
Ni1—Cl1	2.2150 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯Cl1i	0.98	2.94	3.808 (4)	148
C5—H5A⋯Cl1ii	0.98	2.91	3.777 (4)	148

Symmetry codes: (i) ; (ii) .