1,3-Bis[(naphthalen-2-ylsulfanyl)methyl]benzene

Molecules of the title compound, C28H22S2, are located on a crystallographic mirror plane with one half-molecule in the asymmetric unit. The dihedral angle between the phenyl ring and the naphthyl unit is 83.14 (7)°. In the crystal, molecules are interconnected by C—H⋯S and C—H⋯π interactions.

Molecules of the title compound, C 28 H 22 S 2 , are located on a crystallographic mirror plane with one half-molecule in the asymmetric unit. The dihedral angle between the phenyl ring and the naphthyl unit is 83.14 (7) . In the crystal, molecules are interconnected by C-HÁ Á ÁS and C-HÁ Á Á interactions.
RRM thanks CONACYT for a posdoctoral scholarship (agreement No. 290586-UNAM). Support of this research was provided by CONACYT (grant No. 154732)   Among these species, those including sulfur as donor atom have been scarcely studied (Arroyo et al., 2003), mostly due to the well known tendency of sulfur to kill the activity of homogeneous catalysts. Thus, following our continuous interest in the synthesis of pincer type ligands we report the crystal structure of the potentially pincer sulfur based ligand 1,3-bis((naphthalen-2-ylthio)methyl)benzene.
In the asymmetric unit only half of the molecule of the compound 1,3-bis(naphthalen-2-ylthio)methyl)benzene is found.
The other half is generated by a mirror plane. The molecular structure of the title compound is shown in Figure 1. The phenyl and the naphthyl enclose a dihedral angle of 83.14 (7)°. The two naphthyl planes have a dihedral angle of 45.64 (4)°. The sulfur atoms form weak hydrogen bonds (C5-H5···S1). Two C-H···π interactions [C1-H1···Cg1 and C13-H13···Cg2] further connect the molecules into ribbons running along the a-axis

Figure 1
The molecular structure of the title compound with displacement ellipsoids at the 40% probability.

Figure 2
The title compound is linked by C-H···S and C-H···π intermolecular interactions along the a axes, the hydrogen atoms for the interactions are drawn.

1,3-Bis[(naphthalen-2-ylsulfanyl)methyl]benzene
Crystal data 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.