2-Hydroxy-3-nitro-N-phenylbenzamide

The asymmetric unit of the title compound, C13H10N2O4, contains two crystallographically independent molecules. The aromatic rings are oriented at dihedral angles of 24.39 (3) and 7.47 (3)° in the two molecules and intramolecular N—H⋯O and O—H⋯O hydrogen bonds result in the formation of two planar six-membered rings. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains, forming R 2 2(10) ring motifs. Weak π–π contacts between the benzene and phenyl rings [centroid–centroid distance = 3.955 (3) Å] may further stabilize the structure.

The asymmetric unit of the title compound, C 13 H 10 N 2 O 4 , contains two crystallographically independent molecules. The aromatic rings are oriented at dihedral angles of 24.39 (3) and 7.47 (3) in the two molecules and intramolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds result in the formation of two planar six-membered rings. In the crystal structure, intermolecular O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds link the molecules into chains, forming R 2 2 (10) ring motifs. Weakcontacts between the benzene and phenyl rings [centroidcentroid distance = 3.955 (3) Å ] may further stabilize the structure.
title compound, (I), is an intermediate for their preparation. It will also be utilized for the complexation with various metals.
We report herein the crystal structure of (I).
The crystal structure of N-(2-Methoxyphenyl) 2-hydroxy-5-methyl-3-nitro-benzamide, (II) (Yi et al., 2007) has been published, which is different from (I) due to the substitution of methoxy on N-phenyl and methyl group on the nitro containing aromatic ring.

Experimental
For the preparation of the title compound, a solution of N-phenyl 2-hydroxy-benzamide (5.3 g, 0.025 mol) in ethylacetate (EtOAc) (25 ml) was added dropwise to a nitrating mixture of HNO 3 (2.25 ml, 3.15 g, 0.05 mol) and H 2 SO 4 (1.33 ml, 2.45 g, 0.025 mol), with constant stirring, while the temperature was kept below 278 K. The reaction mixture was refluxed for 5 h, cooled, neutralized with aqueous NaHCO 3 (10%) and extracted with EtOAc (3 × 25 ml). The organic layer was combined, dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure to afford reddish brown solid.