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

Abstract

water molecule O1W forming an R 3 3 (10) ring (Fig. 1, Table 2). The other water O2W is positioned between O1W and the isoindole O3A, providing a complex arrangement of hydrogen-bonded rings with motifs R 3 3 (10)R 3 3 (11)[R 4 4 (15)] (Bernstein et al., 1995). Dimers link through (aryl A/B)O4-H4Á Á ÁO3=C3 B/A hydrogen bonds, forming a one-dimensional chain of rings connected as graph set R 2 2 (22) (Fig. 2), that associate further through centres of symmetry forming a column along [101], comprising two chains of rings linked and oriented in opposite directions. Such R 2 2 (22) rings are also a key feature in the crystal structure of (II). In (I), the column can also be described as assembling from dimers into tetramers (Fig. 3) and association into columns through (aryl)O-HÁ Á ÁO C interactions (Fig. 4). Columns interlock viaarene stacking interactions about inversion centres, forming ruffled sheets [isoindole C 6 ring interplanar distance of 3.37 Å , substantially offset with Cg1Á Á ÁCg1 vii = 3.769 (2) Å , where Cg1 is the C4B-C9B ring centroid and symmetry code: (vii) Àx, Ày, Àz], in tandem with C-HÁ Á Á(arene) interactions (Fig. 5, Table 2) and C-HÁ Á ÁO interactions. The cumulative effect yields a complex hydrogenbond pattern as a three-dimensional network (Fig. 6). The hydrogen bonding network involving O1W and O2W is uncommon as O2W forms only one strong hydrogen bond (Figs. 1-3). Water O1W is an acceptor for the acidic O1B-H1B group [OÁ Á ÁO = 2.610 (3) Å , Table 2]. The O1W-H1 donor forms a bifurcated interaction with O3B iii /O2A [OÁ Á ÁO 2.982 (3)/3.149 (3) Å : symmetry operation iii, Table 2] and organic papers o2208 Gallagher and Brady C 17 H 15 NO 4 ÁH 2 O