The title compound, CI7HIsNO3, forms a hydrogenbonded network in the solid state consisting of O-H-.

No abstract

The title compound, C17H15NO4, derived from l‐tyrosine, crystallizes with three independent mol­ecules which differ in the conformation of the asymmetric unit: the N—C—C—Cipso torsion angles are −71.7 (5), −63.6 (6) and −52.5 (5)°, respectively. Deformations in the phenol ring hydroxy O—C—C angles of 116.5 (4)/123.9 (4), 121.7 (5)/118.1 (4) and 122.4 (5)/118.6 (5)°, respectively, result from their respective intermolecular hydrogen‐bonding environments. Intermolecular Oacid—H⃛O=Cindole, Ophenol—H⃛O—Hphenol and Ophenol—H⃛O=Cindole hydrogen bonds, with O⃛O distances in the range 2.607 (4)–2.809 (4) Å, are present in combination with C—H⃛O and C—H⃛πarene interactions. The primary hydrogen‐bonding systems assemble with graph sets R33(8) and R32(22).

In the ®rst of the title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, C 13 H 15 NO 3 , prepared from l-norvaline, a hydrogen-bonded network is formed in the solid state through OÐHÁ Á ÁO C, CÐHÁ Á ÁO C and CÐ HÁ Á Á% arene intermolecular interactions, with shortest OÁ Á ÁO, CÁ Á ÁO and CÁ Á Ácentroid distances of 2.582 (13), 3.231 (11) and 3.466 (3) A Ê , respectively. In the l-valine derivative, (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, C 13 H 15 NO 3 , OÐHÁ Á ÁO C and C arene ÐHÁ Á ÁO C intermolecular interactions generate a cyclic R 2 2 (9) motif through cooperativity, with shortest OÁ Á ÁO and CÁ Á ÁO distances of 2.634 (3) and 3.529 (5) A Ê , respectively. Methylene CÐ HÁ Á ÁO C indole interactions complete the hydrogen bonding, with CÁ Á ÁO distances ranging from 3.283 (4) to 3.477 (4) A Ê . CommentPhthalimidines (isoindolin-1-ones) often display biological activity as potential anti-in¯ammatory agents and antipsychotics (Mukherjee et al., 2000), and most of the structurally determined systems are either N-substituted or have a hydroxy substituent at the 3-position (McNab et al., 1997;Kundu et al., 1999). Amino acids constitute a fundamental building block in biological compounds and valine derivatives have been utilized in the formation of chiral host lattices (Weigand et al., 1998). The title compounds, (2S)-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)pentanoic acid, (I), and (2S)-3-methyl-2-(1-oxo-1H-2,3-dihydroisoindol-2-yl)butanoic acid, (II), derived from l-norvaline and l-valine, respectively, form part of a systematic study of hydrogen-bonding interactions in a series of amino acid derivatives (Brady et al., 1998;Dalton et al., 1999;Gallagher & Murphy, 1999;Gallagher et al., 2000).Compound (I) crystallizes in space group P2 1 2 1 2 1 with one molecule in the asymmetric unit and a view of (I) with the atomic numbering scheme is given in Fig. 1, with selected dimensions in Table 1. The bond lengths and angles in the heterocyclic ring are similar to those reported previously (McNab et al., 1997;Brady et al., 1998;Gallagher & Murphy, 1999) and are in agreement with expected values (Orpen et al., 1994). The carboxylic acid group exhibits rotational disorder, with site occupancies of 0.55 (4) and 0.45 (4) for the major and minor orientations, respectively. The angle between the CO 2 planes is 31 (3) and the major CO 2 orientation is at an angle of 67 (2) to the C 4 N ring plane [87.1 (16) for the minor site]. The angle between the ®ve-and six-membered rings of the isoindole system is 1.37 (17) and the maximum deviation from planarity for an atom in either ring plane is 0.0084 (16) A Ê for C9 (C 6 ring), with the carbonyl O3 atom 0.026 (3) A Ê from the C 4 N ring plane. The n-propyl chain adopts two conformations, with site occupancies of 0.519 (11) and 0.481 (11); details are given in the Experimental section.The hydrogen bonding in (I) is dominated by OÐ HÁ Á ÁO C, CÐHÁ Á ÁO C and C arene ÐHÁ Á Á% arene intermolecular interactions (Table 2 and Fig. 2). Convention...

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