(Isopropyl xanthato-κ2 S,S′)bis(1,10-phenanthroline-κ2 N,N′)sodium(I)

The title compound, [Na(C4H7OS2)(C12H8N2)2], is monomeric, with the Na atom chelated by the S atoms of an i-propylxanthate ligand and the N atoms of two 1,10-phenanthroline (phen) ligands. The Na atom is six-coordinate in a distorted trigonal antiprism. A number of π–π stacking interactions involving the phen rings help to consolidate the crystal packing (centroid–centroid distances lie in the range 3.338–3.443 Å).

The title compound, [Na(C 4 H 7 OS 2 )(C 12 H 8 N 2 ) 2 ], is monomeric, with the Na atom chelated by the S atoms of an ipropylxanthate ligand and the N atoms of two 1,10phenanthroline (phen) ligands. The Na atom is six-coordinate in a distorted trigonal antiprism. A number ofstacking interactions involving the phen rings help to consolidate the crystal packing (centroid-centroid distances lie in the range 3.338-3.443 Å ).

S1. Comment
So far only a handful of sodium chalcogenolates have been investigated in the solid state (Arnold et al., 1995). As a continuation of our interest in sulfur-containing ligands, in this paper we report the synthesis and structural characterization of the title compound, (I).
The title compound, (I), is monomeric, with the Na atom chelated by the S atoms of an i-propylxanthate ligand and the nitrogen atoms of two 1,10-phenanthroline ligands (Fig. 1). The metal is six-coordinate in a coordination polyhedron that can be described as a distorted trigonal antiprism. The plane defined by S1, N1 and N3 is essentially parallel to that defined by S2, N2 and N4 (the two planes are inclined by 7.1°) and Na is displaced by 1.35 and 1.24 Å away from these planes, respectively.
A number of π-π stacking interactions involving the phen rings help to consolidate the crystal packing (Fig. 2). The Cg···Cg (Cg = ring centroid) distances lie in the range 3.338-3.443 Å, which is normal for such interactions (Janiak, 2000) and lead to the formation of an infinite one-dimensional chain network structure along the a axis.

S2. Experimental
To an acetonitrile solution of NaI (1.0 mmol) was added another acetonitrile solution of sodium i-propylxanthate (1.0 mmol) and phenanthroline (2.0 mmol). The resulting solution was stirred for 3.0 h at room temperature and a yellow-red solid was obtained by filtration. The product was recrystallized in acetone to give yellow-red crystals. Yield 82%.

S3. Refinement
All H atoms were positioned geometrically and treated as riding on their parent atoms [C-H = 0.93Å and U iso = 1.2*U eq (C) for CH (aromatic), C-H = 0.96Å and U iso = 1.5*U eq (C) for CH 3 , C-H = 0.98Å and U iso = 1.2*U eq (C) for CH  The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Figure 2
Crystal packing of (I) showing π-π stacking interactions (dashed lines) along the a axis.

Crystal data
[Na(C 4 H 7 OS 2 ) (C 12    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.