Crystal structure of (7-methyl-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate

In the title compound, C17H19NO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.0383 (28) Å, and the piperidine ring adopts a chair conformation. The 2H-chromene ring makes dihedral angles of 32.89 (16) and 67.33 (8)°, respectively, with the mean planes of the piperidine ring and the carbodithioate group. In the crystal, C—H⋯O and weak C—H⋯S hydrogen bonds link the molecules into chains along [001]. The crystal structure also features C—H⋯π and π–π interactions, with a centroid–centroid distance of 3.7097 (17) Å.


S1. Comment
Coumarins and their derivatives play an important role in the agricultural and pharmaceutical industries (Stiefel et al., 1995). They are widely present in higher plants such as Rutaceae, Apiaceae, Asteraceae, Leguminosae, Thymelaeaceae, and they also occur as animal and microbial metabolites (Murray et al., 1982). Most of them show a wide spectrum of pharmacological effects, including antimicrobial (Khan et al., 2004), anti-arrhythmic, antiosteoporosis, anti-HIV, and antitumor activities (Kawaii et al., 2001;Yu et al., 2003). Accordingly, many reports have described various structures and biological evaluations of numerous coumarin analogs newly synthesized or isolated from plants.
Sulfur containing molecules are currently under study as chemoprotectants in chemotherapy. Organic substances with a dithio functional group have been widely used in industry as rodent repellents, vulcanization additives in rubber manufacturing, additives in lubricants, and in agriculture as fungicides on almond trees, stone fruits, and vegetables.

S2. Experimental
The title compound compound was prepared according to a reported method (Kumar et al., 2013). Colourless needles of the title compound were grown from a mixed solution of EtOH/CHCl 3 (v/v = 1/1) by slow evaporation at room temperature. Yield: 80%, m.p. 420 K.

S3. Refinement
All H atoms were positioned geometrically, with C-H = 0.93 Å for aromatic H, C-H = 0.97 Å for methylene H and C -H = 0.96 Å for methyl H,and refined using a riding model with U iso (H) = 1.5U eq (C) for methyl H and U iso (H) = 1.2U eq (C) for all other H.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.

Figure 2
Crystal packing for the title compound with hydrogen bonds drawn as dashed lines.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.15995 (