Pseudopolymorphism of N-acetyl-L-phenylalanine methyl ester

The structures of two pseudopolymorphs of N-acetyl-L-phenylalanine methyl ester, L-AcFOMe, were determined at both 293 (2) and 150 (2) K. At room temperature, the orthorhombic phase C12H15NO3 (I), with space group P2(1)2(1)2(1), converts into the tetragonal phase C12H15NO3 center dot-0.5H(2)O (II), with space group P4(1)2(1)2, in the presence of water. In the structures of both pseudopolymorphs, alternating layers of hydrophilic and hydrophobic intermolecular interaction can be distinguished. In the hydrophilic layers the structures are stabilized by moderate hydrogen bonds of the type N-H center dot center dot center dot O for the anhydrous L-AcFOMe and of types N-H center dot center dot center dot O and O-H center dot center dot center dot O for the hemihydrate. Weak C-H center dot center dot center dot pi interactions are observed within the hydrophobic layers: for (I) they are of type III [ Malone et al. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436], whereas typical type I edge-to-face interactions are present for (II). The differences between the hydrogen-bonding networks of (I) and (II) are discussed in terms of graph-set analysis.