trans-(4-Acetylnaphthyl)chloridobis(triphenylphosphine-κP)nickel(II) dichloromethane solvate

The title compound, [Ni(C12H9O)Cl(C18H15P)2]·CH2Cl2, was synthesized from the reaction between 1-acetyl-4-chloronaphthalene, NiCl2·6H2O and triphenylphosphine (PPh3) in ethanol. The compound contains one crystallographically unique nickel ion in a pseudo-square-planar geometry.


Experimental
Crystal data [Ni(C 12  that it is possible to use such complexes as catalyst in cross-coupling reactions. Consequently, we were interested in the synthesis and direct application of Ni(II)-(σ-aryl) complex catalysts for carbon-heteroatom coupling. In particular, we are investigating a type of isolatable trans-haloarylbis(triphenylphosphine)nickel(II) that is readily available and air-and thermally stable (Chen & Yang, 2007). For this purpose, we have synthesized the title compound in an analogous fashion to a previous literature precedent (Brandsma et al. 1998).
The reaction between NiCl 2 . 6H 2 O, PPh 3 and 1-acetyl-4-chloronaphthalene in ethanol leads to the formation the title compound (I) in high yield. The Ni 2+ metal centre of the complex displays a pseudo-square-planar geometry ( Figure I).

S3. Refinement
All nine restraints were used to make the refinement of the slightly disordered solvent, dichloromethane, more stable. Six of the restraints were used to make the anisotropic displacement parameters of C49 in dichloromethane approximately isotropic. The other three restraints were used to make the components of the anisotropic displacement parameters in the direction of the C-Cl bond in dichloromethane approximately equal. H atoms were fixed geometrically and allowed to ride on their parent atoms, with C-H distances of 0.93-0.97 Å, and with U iso =1.2-1.5U eq of the parent atoms.

Figure 1
A view of the complex, Ellipsoids are drawn at the 30% probability level.

trans-(4-Acetylnaphthyl)chloridobis(triphenylphosphine-κP)nickel(II) dichloromethane solvate
Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.