Received 1 December 2011
In the title compound, C11H12ClNO3, the conformation of the N-H bond in the amide segment is syn with respect to the ortho-Cl atom. The amide and carboxyl C=O groups are syn to each other. Furthermore, the C=O and O-H bonds of the carboxyl group are in syn positions with respect to each other. The dihedral angle between the benzene ring and the amide group is 47.8 (2)°. In the crystal, molecules are connected by pairs of O-HO hydrogen bonds, forming inversion dimers. The dimers are further linked by N-HO hydrogen bonds into double chains along the b-axis direction.
For our previous studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2001); Saraswathi et al. (2011), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005) and on N-chloroarylamides, see: Gowda et al. (1996). For modes of hydrogen bonding in the structures of carboxylic acids, see: Leiserowitz (1976). For the centrosymmetrical dimeric hydrogen-bonding association of carboxylic groups, see: Jagannathan et al. (1994).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2035 ).
BSS thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.
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