Crystal structure and Hirshfeld surface analysis of 1-carb-oxy-2-(3,4-di-hydroxy-phen-yl)ethan-1-aminium bromide 2-ammonio-3-(3,4-di-hydroxy-phen-yl)propano-ate

Acta Crystallogr E Crystallogr Commun. 2016 Oct 7;72(Pt 11):1544-1548. doi: 10.1107/S2056989016015425. eCollection 2016 Nov 1.

Abstract

In the title mol-ecular salt, C9H12NO4+·Br-·C9H11NO4, one of the dopa mol-ecules is in the cationic form in which the α-amino group is protonated and the α-carb-oxy-lic acid group is uncharged, while the second dopa mol-ecule is in the zwitterion form. The Br- anion occupies a special position and is located on a twofold rotation axis. The two dopa mol-ecules are inter-connected 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: Hirshfeld surfaces; crystal structure; cyclic N—H⋯Br hydrogen bonds; dopa; hydrogen bonding.