Crystal structure and Hirshfeld surface analysis of 1-carboxy-2-(3,4-dihydroxyphenyl)ethan-1-aminium bromide 2-ammonio-3-(3,4-dihydroxyphenyl)propanoate

Abstract

In the title molecular salt, C9H12NO4+·Br−·C9H11NO4, one of the dopa molecules is in the cationic form in which the α-amino group is protonated and the α-carboxylic acid group is uncharged, while the second dopa molecule is in the zwitterion form. The Br− anion occupies a special position and is located on a twofold rotation axis. The two dopa molecules are interconnected by short O—H...O hydrogen bonds. In the crystal, the various units are linked by O—H...O, N—H...Br and N—H...O hydrogen bonds, forming a three-dimensional framework. The title compound was refined as an inversion twin with an absolute structure parameter of 0.023 (8).

Keywords

• crystal structure
• dopa
• cyclic N—H...Br hydrogen bonds
• hydrogen bonding
• Hirshfeld surfaces