Bis(2,4-dinitrophenyl)sulfane

In the title compound, C12H6N4O8S, the dinitrophenyl rings subtend an angle of 78.46 (13) °. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds leading to the formation of a two-dimensional network lying parallel to the bc plane.

In the title compound, C 12 H 6 N 4 O 8 S, the dinitrophenyl rings subtend an angle of 78.46 (13) . In the crystal, molecules are linked by weak C-HÁ Á ÁO hydrogen bonds leading to the formation of a two-dimensional network lying parallel to the bc plane.   Table 1 Hydrogen-bond geometry (Å , ). supplementary materials . E68, o3116 [doi:10.1107/S1600536812041803]

Bis(2,4-dinitrophenyl)sulfane M Buvaneswari, D Kalaivani and M Nethaji Comment
The title sulfur containing organic compound is a biologically active molecule (Andricopulo et al., 2006). It has been utilized in many clinical trials (Nakadate et al., 1964;Alekhina et al., 1978) and also employed in the synthesis of a number of other important organic molecules (Parihar et al., 1971;Evans & Kinnard, 1983). Several methods have been reported for the synthesis of the title molecule (Pesin et al., 1963;Joshi & Mathur, 1963;Obata et al., 1966;Stepanov et al., 1974;Davydov & Beletskaya, 2003). In continuation of our previous work to synthesize new substituted barbiturates when 2-thiobarbituric acid is used (Manickkam & Kalaivani, 2011;Rajamani & Kalaivani, 2012) , the title molecule was obtained crystallizing out as the product through a new synthetic route.
In the title molecule ( Fig. 1) the two phenyl rings are inclined to one another by 78.46 (13) °.
In the crystal, there are a number of weak C-H···O hydrogen bonds linking the molecules to form a two-dimensional network lying parallel to the bc plane (Table 1 and Fig. 2).

Experimental
Analytical grade 1-chloro-2,4-dinitrobenzene (2.02 g, 0.01 mol) dissolved in ethanol (20 ml) and 2-thiobarbituricacid (1.44 g, 0.01 mol) dissolved in ethanol (20 ml) were mixed. Triethylamine (5 g,0.05 mol) was then added and the mixture was shaken well for 5-6 hrs. On standing yellow crystals came out from the solution after 5 days. The crystals were filtered and washed well with ether to remove the unreacted reactants and then with a small amount of absolute alcohol.
The crystals were recrystallized from ethanol (M.pt: 467 K; yield: 70%). Good quality single crystals for X-ray diffraction studies were obtained by slow evaporation of a solution in ethanol at room temperature.

Refinement
All the H atoms were included in calculated positions and treated as riding: C-H = 0.93 Å with U iso (H) = 1.2U eq (C).  A view of the molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
A view along the b axis of the crystal packing of the title compound. The C-H···O hydrogen bonds are shown as dashed cyan lines (H atoms not involved in these interactions have been omitted for clarity; see Table 1 for details). where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.21 e Å −3 Δρ min = −0.19 e Å −3

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles 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 > 2σ(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.