Crystal structure of bis[1-(naphthalen-1-ylmethyl)pyridinium] bis(2,2-dicyanoethene-1,1-dithiolato-κ2 S,S′)nickelate(II)

In the ion-pair complex, bis[1-(naphthalen-1-ylmethyl)pyridinium] bis(2,2-dicyanoethene-1,1-dithiolate-κ2 S,S′)nickelate(II), C—H⋯N and C—H⋯Ni hydrogen bonds as well as π–π interactions between the ions result in the formation of a three-dimensional network.


Supramolecular features
There are three weak interactions between the Ni(imnt) 2 2À anion and [1-NaMePy] + cation. The first is acontact between the chelate ring (which is defined by atoms Ni1, S1, S2, and C1) of the anion and the pyridinium ring of the cation (Fig. 2) with a distance of 3.675 (2) Å between the centroids. The second is a C-HÁ Á ÁNi hydrogen bond and the third is a C-HÁ Á ÁN hydrogen bond (Table 1, Fig. 3). The combination of these weak interactions consolidates the title complex into a three-dimensional network structure (Fig. 3).

Figure 1
The molecular structure of (I), with the atom labelling and 30% probability displacement ellipsoids for non-H atoms The other half of the anion is generated by the inversion-symmetry operation Àx, y + 1 2 , Àz + 1 2 .

Figure 2
Thecontact between the chelate ring of the anion and the pyridinium ring of the cation (shown as a dashed line).

Figure 3
The packing of the title compound, viewed down the a axis, showing the network of molecules connected by C-HÁ Á ÁN hydrogen bonds (dashed lines).

Bis[1-(naphthalen-1-ylmethyl)pyridinium] bis(2,2-dicyanoethene-1,1-dithiolato-κ 2 S,S′)nickelate(II)
Crystal data (C 16  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.21 e Å −3 Δρ min = −0.15 e Å −3 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.