3-(2-Hydroxy-5-methylanilino)isobenzofuran-1(3H)-one1

In the molecule of the title compound, C15H13NO3, the phthalide ring system is virtually planar, with a dihedral angle of 1.98 (3)° between the fused five- and six-membered rings. The substituted aromatic ring is oriented at a dihedral angle of 57.50 (3)° with respect to the phthalide ring system. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network.

In the molecule of the title compound, C 15 H 13 NO 3 , the phthalide ring system is virtually planar, with a dihedral angle of 1.98 (3) between the fused five-and six-membered rings. The substituted aromatic ring is oriented at a dihedral angle of 57.50 (3) with respect to the phthalide ring system. In the crystal structure, intermolecular O-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds link the molecules, forming a three-dimensional network.

S1. Comment
The present work is part of a structural study of compounds of 3-substituted phthalides, and we report here the crystal structure of the title compound, (I).
The molecule of (I), (Fig. 1 Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 57.50 (3)°.
In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules by C(4) chains ( Fig. 2) (Bernstein et al., 1995;Etter, 1990), to form a three-dimensional network (Fig. 3), in which they may be effective in the stabilization of the structure.

S2. Experimental
The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 2-aminophenol as starting materials (yield; 80%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.  The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.  A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines [symmetry code: (i) 1 -x, -y, z + 1/2]. H atoms not involved in hydrogen bondings have been omitted for clarity.  (2) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.