(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl diethyldithiocarbamate

In the title compound, C17H21NO2S2, the coumarin ring system is nearly planar, with a maximum deviation of 0.080 (2) Å from the mean plane. An intramolecular C—H⋯S hydrogen bond occurs. The crystal structure features C—H⋯S hydrogen bonds and weak π–π interactions with a centroid–centroid distance of 3.679 (1) Å.

In the title compound, C 17 H 21 NO 2 S 2 , the coumarin ring system is nearly planar, with a maximum deviation of 0.080 (2) Å from the mean plane. An intramolecular C-HÁ Á ÁS hydrogen bond occurs. The crystal structure features C-HÁ Á ÁS hydrogen bonds and weakinteractions with a centroid-centroid distance of 3.679 (1) Å .
In view of the above observations,we proposed that 4-substituted coumarins bearing the dithiocarbamate (DTC)group should display some interesting biological activity and the title compound was screened for fungicidal, bacterial and DNA cleavage properties.The crystal structure of a coumarin derivative linked to the DTC group has been reported (Kumar et al., 2012).
The title compound is one of a series of dithiocarbamate coumarins with potential as possible anti-microbial agents. For these reasons, in continuation of our interest in the crystal structures of coumarin derivatives, we report here its crystal structure.

Experimental
All the chemicals were of analytical reagent grade and were used directly without further purification. 4-Bromomethyl coumarin required for the synthesis of the target molecule was synthesized according to an already reported procedure involving Pechmann cyclization of phenols with 4-bromoethyl acetoacetate (Shastri et al., 2004) and sodium diethyldithiocarbamate purchased from Sigma-Aldrich. A mixture of 2.6 g (0.01 mol) of 5,7-dimethyl-4-bromomethylcoumarin and 1.71 g (0.01 mol) of sodium diethyldithiocarbamate in 30 ml dry alcohol was stirred for 24 h at room temperature (the reaction was monitored by TLC). The solvent was evaporated and the resulting solid was extracted twice with a dichloromethane-H 2 O mixture. The organic layer was dried over anhydrous CaCl 2 and evaporation of the organic solvent gave the title compound. The compound was recrystallized from an ethanol-chloroform mixture. Colour: Colourless. Yield: 91%. M.P.: 409 K.

Computing details
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).   The packing of the molecules in the crystal structure. 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.