Crystal structure and Hirshfeld surface analysis of 1-carb-oxy-2-(3,4-di-hydroxy-phen-yl)ethan-1-aminium chloride 2-ammonio-3-(3,4-di-hydroxy-phen-yl)propano-ate: a new polymorph of l-dopa HCl and isotypic with its bromide counterpart.

The title mol-ecular salt, C9H12NO4(+)·Cl(-)·C9H11NO4, is isotypic with that of the bromide counterpart [Kathiravan et al. (2016 ▸). Acta Cryst. E72, 1544-1548]. The title salt is a second monoclinic polymorph of the l-dopa HCl structure reported earlier in the monoclinic space group P21 [Jandacek & Earle (1971 ▸). Acta Cryst. B27, 841-845; Mostad & Rømming (1974 ▸). Acta Chemica Scand. B28, 1161-1168]. In the title compound, monoclinic space group I2, one of the dopa mol-ecules has a positive charge with a protonated α-amino group and the α-carb-oxy-lic acid group uncharged, while the second dopa mol-ecule has a neutral charge, the α-amino group is protonated and the α-carb-oxy-lic acid is deprotonated. In the previously reported form, a single dopa mol-ecule is observed in which the α-amino group is protonated and the α-carb-oxy-lic acid group is uncharged. The invariant and variations of various types of inter-molecular inter-actions present in these two forms of dopa HCl structures are discussed with the aid of two-dimensional fingerprint plots.