Crystal structure and Hirshfeld surface analysis of ethyl 2-{[4-ethyl-5-(quinolin-8-yloxymethyl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate

In the title compound, the 1,2,4-triazole ring is twisted with respect to the mean plane of quinoline moiety at 65.24 (4)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds.


Chemical context
Quinoline derivatives are a very important class of nitrogencontaining heterocycles, which display a broad range of biological activities (Srikanth et al., 2010). In addition, quinolines have suitable electron mobility and other important properties which are crucial for their use in organic lightemitting diodes (OLEDs) (Chen & Shi, 1998;Kulkarni et al., 2004). They are also used in the synthesis of molecules having non-linear optical properties (MacDiarmid et al., 1997;Epstein, 1997). The 1,2,4-triazole ring is also a major fivemembered heterocyclic ring, which serves as the core component of many substances that display a wide range of biological activities (Mathew et al., 2007;Pelz et al., 2001). This heterocycle is an important structural motif in the design of new drugs (Catarzi et al., 2004). Here we report the molecular and crystal structure of the title 1,2,4-triazole derivative.

Supramolecular features
In the crystal, weak C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds (Table 1, Fig. 2) link the molecules into a three dimensional supramolecular architecture.stacking involving the quinoline rings is also observed, with the intercentroid distance being 3.6169 (6) Å .

Hirshfeld surface analysis
To understand the different interactions and contacts in the crystal structure, it is necessary to represent Hirshfeld surface (HS) and generate fingerprint plots which provide quantitative information for each intermolecular interaction. In order to highlight all intra-and intermolecular interactions, HS analyses were performed and fingerprint plots were drawn using Crystal Explorer (Wolff et al., 2007). The three-dimensional Hirshfeld surface generated for the structure of the title crystal is presented in Fig. 3  The molecular structure of the title molecule, showing the atomic numbering scheme (displacement ellipsoids are drawn at the 65% probability level). H atoms are shown as small spheres of arbitrary radii. Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx þ 2; y À 1 2 ; Àz þ 1; (ii) x þ 1; y; z þ 1; (iii) x; y; z À 1; (iv) x À 1; y; z.

Figure 2
Crystal packing diagram of the title compound viewed along the c axis with hydrogen bonds shown as dashed lines. been mapped over a d norm range of À0.191 to 1.247 Å . The large deep-red spots on the d norm HS indicate the close-contact interactions, which are mainly responsible for significant hydrogen-bonding contacts. The 2D fingerprint plot is depicted in Fig. 4. This indicates that the most important contacts on the surface, which are necessary for organic molecules, are the HÁ Á ÁH contacts with a percent contribution of 47.7% to the HS area of the title molecule.

Ethyl 2-{[4-ethyl-5-(quinolin-8-yloxymethyl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate
Crystal data 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.