Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases

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 (C(29)H(34)FN(5)S) (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 (C(30)H(36)FN(5)OS) (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)°, respectively, and the two aryl rings are inclined to one another by 66.37 (13)°. In compound (II), the corresponding dihedral angles are 83.35 (13), 71.38 (15) and 11.97 (16)°, respectively. The crystal structure of (I) shows pairs of C—H⋯F hydrogen bonds forming inversion dimers, while in the crystal of compound (II), in addition to the C—H⋯F hydrogen bonds that generate chains parallel to the b axis, there are C—H⋯π inter­actions present that link the chains to form layers parallel to the ab plane.