Research Article: 3-(1-Adamant­yl)-4-amino-1-(2-benzoyl-1-phenyl­eth­yl)-1H-1,2,4-triazol-5(4H)-thione

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Siham Lahsasni, Ali A. El-Emam, Nasser R. El-Brollosy, Ching Kheng Quah, Hoong-Kun Fun.


In the title compound, C27H30N4OS, the 3-(adamantan-1-yl)-4-amino-1H-1,2,4-triazole-5(4H)-thione unit and the O atom are each disordered over two sets of sites with refined site-occupancies of 0.7630 (13) and 0.2370 (13). The 1,2,4-triazole ring of the major component forms dihedral angles of 62.61 (17) and 61.93 (16)° with the benzene rings, while that of the minor component makes corresponding angles of 86.3 (4) and 79.1 (4)°. The dihedral angle between the benzene rings is 39.21 (16)°. The mol­ecular structure is stabilized by an intra­molecular C—H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯S hydrogen bonds.

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For the biological activity of adamantane derivatives, see: Vernier et al. (1969 ▶); Kadi et al. (2007 ▶, 2010 ▶); Al-Abdullah et al. (2007 ▶); El-Emam et al. (2004 ▶). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2012 ▶); Almutairi et al. (2012 ▶); Al-Tamimi et al. (2010 ▶). For related amino-1,2,4-triazole structures, see: Song et al. (2011 ▶); Gao et al. (2011 ▶); Wang et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).