[(Dibenzo[b,d]thiophen-4-yl)tellanyl]methanethiol

In the title compound, C13H10S2Te, the dibenzothiophene moiety is almost planar, the maximum atomic deviation being 0.055 (5) Å. The two Te—C bonds are nearly perpendicular to each other with a C—Te—C bond angle of 93.0 (2)°. An intermolecular C—H⋯π interaction is present between the methylene group and thiophene ring.

In the title compound, C 13 H 10 S 2 Te, the dibenzothiophene moiety is almost planar, the maximum atomic deviation being 0.055 (5) Å . The two Te-C bonds are nearly perpendicular to each other with a C-Te-C bond angle of 93.0 (2) . An intermolecular C-HÁ Á Á interaction is present between the methylene group and thiophene ring.

Related literature
For general background to the field-effect transistors of organotellurium derivatives, see: Inokuchi et al. (1987). For related structures, see: Kobayashi et al. (2005).
Cg is the centroid of the thiophene ring.

Comment
The design and synthesis of high-performance organic semiconductor materials have been an active topic in the area of field-effect transistors. Recently, organotellurium compounds have received significant attention due to the high charge carrier mobility (Inokuchi et al., 1987). In this paper, we report the synthesis and the crystal structure of the title compound (I).
The asymmetric unit of the title compound is shown in Fig. 1. The dibenzothiophene group possesses perfect planarity: the dihedral angle between the two phenyls is 4.11°. The two Te-C bonds are nearly perpendicular to each other with a C-Te-C bond angle of 93.0 (2)°. In the packing structure ( Fig. 2), the molecules are packed into molecular columns along the a axis through intermolecular Te···π interactions between the tellurium atom and the phenyl ring (C7-C12). The contact distance of Te···C9 is 3.68 (5) Å, that of Te···C10 is 3.47 (5) Å, and that of Te···C11 is 3.73 (7) Å. These contact distances are significantly shorter than the sum of the van der Waals radii of tellurium and aromatic carbon atoms (Kobayashi et al., 2005). The molecular columns are connected together by intermolecular C···S and S···S interactions. The contact distances of C13···S1 and S1···S2 are 3.43 (5) Å and 3.51 (2) Å, respectively, which are obviously shorter than the sum of the corresponding van der Waals radii. There are no classic hydrogen bonds in the crystal structure.

Experimental
Addition of a 1.6 M solution of n-BuLi in hexane (8.50 ml, 13.6 mmol) to the THF solution of dibenzothiophene (2.50 g, 13.6 mmol) at room temperature under an Ar atmosphere. The reaction mixture was stirred for 2 h, and then tellurium powder (1.70 g, 13.3 mmol) was added. After 3 h, the reaction mixture was poured into a beaker containing 200 ml cold distilled water and oxidized by passing oxygen at a moderate rate for 1 h. The organic solvent was evaporated, and the suspension was extracted with dichloromethane. The organic extracts were washed by brine, and dried by anhydrous CaCl 2 .
After the solvent was removed, the crude product was chromatographed on silica gel using petroleum as eluent to give the title compound (0.27 g, yield 5.56%). Single crystals suitable for X-ray diffraction were obtained by very slow evaporation of a chloroform/ethanol solution.

Refinement
H atoms bonded to C atoms were fixed geometrically and allowed to ride on their attached atoms, with C-H = 0.93-0.97 Å and with U iso (H) = 1.2U eq (C). H atom bonded to S atom was refined using a rotating model, with S-H = 1.20 Å and with U iso (H) = 1.2U eq (S).

Hydrogen-bond geometry (Å, °)
Cg is the centroid of the thiophene ring.