Acta Cryst. (2009). E65, o1557-o1558  [ doi:10.1107/S1600536809021655 ]

4-(sec-Butylamino)-3-nitrobenzoic acid

S. N. Narendra Babu, A. S. Abdul Rahim, S. A. Hamid, C. S. Yeap and H.-K. Fun

Abstract: The asymmetric unit of title compound, C₁₁H₁₄N₂O₄, consists of two crystallographically independent molecules (A and B). In each, intramolecular N-HO hydrogen bonds generate S(6) ring motifs. The mean plane of the nitro group forms dihedral angles of 4.5 (3) and 0.5 (3)° with the benzene ring in molecules A and B, respectively. In molecule A, there is disorder of the butylamino group which corresponds to an approximate 180° rotation about the N-C(H) bond, forming two sites with refined occupancies of 0.722 (6) and 0.278 (6). Molecule B is similarly disordered but in addition there is further rotational disorder about the C(H)-C(H₂) bond giving a ratio of occupancies for three components of 0.42:0.35:0.23. In the crystal structure, intermolecular O-HO hydrogen bonds link molecules into centrosymmetric dimers generating R₂²(8) ring motifs. The crystal structure is also stabilized by weak intermolecular C-HO interactions.

Online 13 June 2009

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