(2RS)-3-(4-Hydroxyphenyl)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl) propanoic acid monohydrate

The title compound, C17H15NO4 center dot H2O, derived from DL-tyrosine crystallizes as an unusual hydrogen-bonded acid monohydrate dimer. The asymmetric unit contains two organic molecules and two water molecules. Dimers link through (aryl)O-H center dot center dot center dot O=C hydrogen bonds along the [101] direction, forming a one-dimensional chain of rings, and further associated via inversion centres ( forming a chain of rings aligned in the opposite direction) generating columns. Ruffled sheets arise from interlocking of isoindole rings via pi-pi(arene) stacking and C-H center dot center dot center dot pi(arene) interactions; C-H center dot center dot center dot O=C interactions generate a three-dimensional network.