Abstract
In the title N-Mannich bases, 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1[( 4-phenylpiperazin-1-yl)methyl]-4,5-dihydro- 1H-1,2,4-triazole-5-thione (C29H34FN5S) (I), and 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1-{[4-(2-methoxyphenyl)piperazin-1-yl]-methyl}-4,5-dihydro-1H-1,2,4-triazole-5-thione (C30H36FN5OS) (II), fluorophenyl, adamantane and piperazine moieties are linked to a planar triazole ring. There is an additional phenyl ring on the piperazine ring in (I) and a methoxyphenyl ring in (II). In compound (I), the fluorophenyl and phenyl rings are inclined to the triazole ring by 86.55 (13) and 60.52 (12)degrees, respectively, and the two aryl rings are inclined to one another by 66.37 (13)degrees. In compound (II), the corresponding dihedral angles are 83.35 (13), 71.38 (15) and 11.97 (16)degrees, respectively. The crystal structure of (I) shows pairs of C-H center dot center dot center dot F hydrogen bonds forming inversion dimers, while in the crystal of compound (II), in addition to the C-H center dot center dot center dot F hydrogen bonds that generate chains parallel to the b axis, there are C-H center dot center dot center dot pi interactions present that link the chains to form layers parallel to the ab plane.