Crystal structure of 11-[4-(hexyloxy)phenyl]-1,2,4-triazolo[4,3-a][1,10]phenanthroline

Abstract

The title compound, C25H24N4O, was prepared from 2-chlorophenanthroline and hexyloxyphenyltetrazole. The main difference between the two independent molecules (AandB) in the asymmetric unit is the orientation of the all-anti-configured hexyloxy chain: inAthe C—O—C—C torsion angle is 175.9 (2)° whereas it is −88.3 (3)° inB. The benzene substitution in the bay of the triazolophenanthroline results in a helical distorsion of the heterocyclic core, the dihedral angles between the mean planes formed by quinoline and benzotriazole ring systems are 13.73 (9) for moleculeAand 14.87 (8)° for B. The dihedral angles between the triazole ring and the attached benzene ring are 45.87 (15) inAand 53.93 (14)° inB. The angular annulation of four rings and the benzene substituent results in a helical distortion of the aromatic framework. The crystal is formed from layers composed of centrosymmetric pairs ofA2,B2molecules with interdigitating alkyl chains.