Crystal structure of methyl 2-[5-(2-hydroxyphenyl)-2H-tetrazol-2-yl]acetate

Abstract

The title compound, C10H10N4O3, was synthesized by the esterification of hydroxyphenyl tetrazole. There is an intramolecular O—H...N hydrogen bond present involving the hydroxy group and the tetrazole ring. The tetrazole ring is inclined to the phenol ring by 2.85 (13)°, while the methyl acetate group is almost normal to the tetrazole ring, making a dihedral angle of 82.61 (14)°. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds, forming inversion dimers. Within the dimers, the phenol rings are linked by offset π–π interactions [intercentroid distance = 3.759 (2) Å]. There are no further significant intermolecular interactions present in the crystal. The hydroxy group is disordered about positions 2 and 6 on the benzene ring, with a refined occupancy ratio of 0.531 (5):0.469 (5).

Keywords

• crystal structure
• tetrazole
• hydroxyphenyl tetrazole
• hydrogen bonding
• offset π–π interactions