Octane-1,8-diylbis[3-ethyl-1H-1,2,4-triazol-5(4H)-one]

Abstract

The title compound, C 16 H 28 N 6 O 2 , has a centre of symmetry. There are two planar 1,2,4-triazole rings, connected by an octane group. The crystal structure is stabilized by CÐHÁ Á ÁN, CÐHÁ Á ÁO and NÐHÁ Á ÁO intermolecular hydrogen bonds. Comment Schiff bases of 4-amino-1,2,4-triazole have received considerable attention over the past few decades (Kitaev et al., 1971; Mazza et al., 1976; Kargin et al., 1988). It is of interest that some of them are anti-in¯ammatory agents (Gupta & Bhargava, 1978) and new concidiostatic drugs (Colauti et al., 1971). Some other diverse pharmacological properties of 1,2,4-triazoles are analgesic, antiasthmatic, diuretic, fungicidal, bactericidal and pesticidal activities (Bennur et al., 1976; Webb & Parsons, 1977; Heubach et al., 1980; Mohamed et al., 1993). Therefore, the structures of 1,2,4-triazole derivatives with different substituents have been the subject of much interest in our laboratory. Examples include 1-acetyl-3-(p-chlorobenzyl)-4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5one, (II) (C Ë oruh, 2002), 1-acetyl-4-(p-chlorobenzylidenamino)-3-acetyl-4,5-dihydro-1H-1,2,4-triazol-5-one, (III) (C Ë oruh, Kahveci, S Ë as Ëmaz, Ag AE ar & Kim, 2003), 1-acetyl-3-(pchlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, (IV) (Ocak et al., 2003), and CÐHÁ Á ÁO and CÐHÁ Á Á% interactions in 1-acetyl-4-(p-chlorobenzylidenamino)-3-ethyl-4,5-dihydro-1H-1,2,4-triazol-5-one, (V) (C Ë oruh, Kahveci, S Ë as Ëmaz, Ag AE ar, Kim & Erdo È nmez, 2003). The molecular structure of (I) is shown in Fig. 1. The compound consists of two 1,2,4-triazole rings, each with an ethyl group on the C atom in the 3-position and an oxo O atom on the C atom at the 5-position, and linked by an octane chain attached to their N atoms at the 4-position. The molecule has a centre of symmetry in the middle of this connecting chain. In the molecule, the placement of the ethyl group and the oxo O atom are very similar to a previously reported example

3-(2-Thienylmethyl)-4,4′-bi-1H-1,2,4-triazol-5(4H)-one

“…1 and 2, respectively. The geometrical parameters of both triazole rings are in very good agreement with literature values (Ç oruh et al, 2003;Zhu et al, 2000). The bond lengths and angles in the thienyl ring of molecule b are normal (Sommerer et al, 1998).…”

4-(2-Pyridylmethyleneamino)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

“…The C6 N1 bond is clearly a double bond, being much shorter than the other C-N bonds in the triazole ring. This distance is also comparable to literature data (Ç oruh et al, 2003;Yilmaz et al, 2005). The crystal structure features centrosymmetric dimers, formed by classical intermolecular N-HÁ Á ÁO hydrogen bonds, involving the amine functionality and the carbonyl of the triazole ring (Table 2).…”

1-(Benzoylmethyl)-4-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one

“…In a previous paper, we reported the synthesis and biological activity of new 1,2,4-triazol-5-one derivatives, in which different substituents were bound to N1 (Demirbaş et al, 2004). We and others (Ç oruh, Ustabaş et al, 2003;Zhu et al, 2000;Li et al, 2004) have also reported spectroscopic and structural data for some bis-1,2,4-triazole-5-ones and structures of 1,2,4-triazole systems with substituents in various positions on the triazole framework. These include 1-acetyl-4-(p-chlorobenzylidenamino)-3-methyl-4,5-dihydro-1H-1,2,4triazol-5-one (Ç oruh, Kahveci, Ş aşmaz, Ag ar & Kim, 2003), 1-acetyl-3-(p-chlorobenzyl)-4-(p-chlorobenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one (Ocak et al, 2003) and 1acetyl-4-(p-chlorobenzylidenamino)-3-ethyl-4,5-dihydro-1H-1,2,4-triazol-5-one (Ç oruh, Kahveci, Ş aşmaz, Ag ar, Kim & Erdö nmez, 2003).…”