2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid

Natalia A. Platosz, Roger A. Lalancette, Hugh W. Thompson, Jacob M. Newman, Ari Schachter

Research output: Contribution to journalArticlepeer-review


The crystal structure of the title compound, C15H12O3, displays catemeric aggregation involving O - H⋯O 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 [001] 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.

Original languageEnglish (US)
Pages (from-to)o1547-o1548
JournalActa Crystallographica Section E: Structure Reports Online
Issue number10
StatePublished - Oct 2013

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics


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