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 (A and B) in the asymmetric unit is the orientation of the all-anti-configured hexyloxy chain: in A the C—O—C—C torsion angle is 175.9 (2)° whereas it is −88.3 (3)° in B. 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 molecule A and 14.87 (8)° for B. The dihedral angles between the triazole ring and the attached benzene ring are 45.87 (15) in A and 53.93 (14)° in B. 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 of A2, B2 molecules with interdigitating alkyl chains.

Keywords

• crystal structure
• phenanthroline
• triazole
• helicene