(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithioate

In the title compound, C19H17NO3S2, the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1)°. In the crystal, weak C—H⋯O interactions link the molecules into corrugated layers parallel to (102). The crystal packing also exhibits π–π interactions, with distances of 3.644 (1) and 3.677 (1) Å between the centroids of the benzene rings of neighbouring molecules.

In the title compound, C 19 H 17 NO 3 S 2 , the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1) . In the crystal, weak C-HÁ Á ÁO interactions link the molecules into corrugated layers parallel to (102). The crystal packing also exhibitsinteractions, with distances of 3.644 (1) and 3.677 (1) Å between the centroids of the benzene rings of neighbouring molecules.

Related literature
For the biological activity of coumarins, see: Kontogiorgis & Hadjipavlou-Litina (2004). For a related structure, see: Kumar et al. (2012). For standard bond lengths, see: Allen et al. (1987).  Table 1 Hydrogen-bond geometry (Å , ).  In (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are in a good agreement with those in related structure (Kumar et al., 2012). The morpholine ring adopts a chair conformation. The dihedral angle bewteen the pyran and benzene rings in the coumarin fragment is 3.9 (1)°. Weak intermolecular C-H···O interactions (Table 1)link the molecules into corrugated layers parallel to (102) plane. The crystal packing exhibits π-π stacking interactions. The first of these is between the benzene ring C4/C5/C10-C13 and its symmetry-related partner at (1-x, 1-y, -z) with a distance of 3.644 (1) Å between the ring centroids. Another π-π interaction is between the benzene ring C4/C5/C10-C13 and the benzene ring C5-C10 at (1-x, 1-y,-z) with a distance of 3.677 (1) Å between the ring centroids.

Experimental
A mixture of 2.73g (0.01 mol) of 7,8-benzo-4-bromomethyl coumarin and 2.00g (0.01 mol) of potassium salt of morpholine-1-dithiocarbomate in 30 ml dry alcohol was stirrer for 12 hours 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 CaCl2, evaporated the solvent and recrystallised from ethanol-chloroform. A slow evaporation technique was used to grow crystals suitable for diffraction studies in an ethanol-chloroform mixture.

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).

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. 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. 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 > 2sigma(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.