(7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate

In the title compound, C16H16ClNO2S2, the piperidine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.5 (1)°. In the crystal, a weak C—H⋯O hydrogen bond links molecules into chains along [001]. In addition, π–π stacking interactions are present involving the benzene and pyran rings, with a centroid-to-centroid distance of 3.712 (2) Å. The crystal studied is a nonmerohedral twin with refined components 0.221 (1) and 0.779 (1).

In the title compound, C 16 H 16 ClNO 2 S 2 , the piperidine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.5 (1) . In the crystal, a weak C-HÁ Á ÁO hydrogen bond links molecules into chains along [001]. In addition,stacking interactions are present involving the benzene and pyran rings, with a centroid-to-centroid distance of 3.712 (2) Å . The crystal studied is a nonmerohedral twin with refined components 0.221 (1) and 0.779 (1).
Dithiocarbamate (DTC) derivatives are valuable compounds due to their interesting chemistry and utility. These compounds have shown wide applications as pesticides, fungicides in agriculture, sulfur vulcanization and anti-cancer agents (Bergendorff & Hansson, 2002;Huang et al., 2009). In our work, we have been able to link a DTC moiety at C-4 methylene carbon and it was a thought of considerable interest to study the effect of this moiety on the total solid-state conformation of the molecule. A new series of piperidine-1-dithiocarbomate derivatives of 4-substituted coumarin was synthesized in a single step and screened for antimicrobial, anti-diabetic, DNA binding and DNA cleavage activity. In this paper we report the crystal structure of (7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate (I).
Experimental 4-Bromomethyl coumarin required for the synthesis of the target molecule was synthesized according to an already reported procedure (Shastri et al., 2004) involving the Pechmann cyclization of phenols with 4-Bromoethyl acetoacetate and the potassium salt of piperidine-1-dithiocarbomate was synthesized according to the procedure reported (Vasilliev & Polackov, 2000).
A mixture of 2.73 g (0.01 mol) of 7-chloro-4-bromomethyl coumarin and 1.99 g (0.01 mol) of potassium salt of piperidine-1-dithiocarbomate in 30 ml dry alcohol was stirred for 12 h at room temperature (the reaction was monitored by TLC). The solvent was evaporated and the solid was extracted twice with MDC-water mixture. The organic solvent was dried over CaCl 2 , the solvent evaporated and recrystallized from ethanol-chloroform.

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C-H distances of 0.93-0.97 Å and with U iso (H) = 1.2U eq (C). The crystal studied is a non-merohedral twin with refined components 0.221 (1) and 0.779 (1) and twin law 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 -1.00.

Computing details
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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: PLATON (Spek, 2009    The packing arrangement of molecules viewed along the a axis. The broken lines show the intermolecular C-H···O interactions. 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.