Received 29 July 2013
The crystal structure of the title compound, C15H12O3, displays catemeric aggregation involving O-HO hydrogen bonds progressing from the carboxyl group of one molecule to the ketone O atom of another glide-related neighbor. The molecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The molecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along  in an A-A-B-B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related molecule.
For a discussion of highly ordered carboxyl bond distances and angles, see: Borthwick (1980). For close contact information, see: Steiner (1997). For related structures, see: Abell et al. (1991); Barcon et al. (1998, 2002); Degen & Bolte (1999); Hickmott et al. (1985); Kashyap et al. (1995); Song et al. (2008); Thompson et al. (1998); Watson et al. (1990). For preparation of the title compound, see: Newman & McCleary (1941). For a description of the Cambridge Structural Database, see: Allen (2002).
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2513 ).
The authors acknowledge support by NSF-CRIF grant No. 0443538.
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