title: Co-crystals of caffeine and hydroxy-2-naphthoic acids: unusual formation of the carboxylic acid dimer in the presence of a heterosynthon.
abstract: A group of caffeine-containing co-crystals of hydroxy-2-naphthoic acids were synthesized and analyzed via single-crystal X-ray diffraction and IR analysis. The imidazole-carboxylic acid synthon was observed in co-crystals involving 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acid. In the case of 6-hydroxy-2-naphthoic acid, the co-crystal exhibits a hydrogen-bonded carboxylic acid dimer in the presence of a hydroxyl-caffeine heterosynthon.
authors.affiliation: Solid State Sciences, Global Pharmaceutical R&D, Abbott Laboratories, North Chicago, Illinois 60064, USA.
authors.forename: Dejan-Kresimir
authors.initials: DK
authors.lastname: Bucar
authors.forename: Rodger F
authors.initials: RF
authors.lastname: Henry
authors.forename: Xiaochun
authors.initials: X
authors.lastname: Lou
authors.forename: Richard W
authors.initials: RW
authors.lastname: Duerst
authors.forename: Thomas B
authors.initials: TB
authors.lastname: Borchardt
authors.forename: Leonard R
authors.initials: LR
authors.lastname: MacGillivray
authors.forename: Geoff G Z
authors.initials: GG
authors.lastname: Zhang
mesh_terms: D002110:Caffeine / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D003460:Crystallization; D018360:Crystallography, X-Ray; D019281:Dimerization; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D033362:Powder Diffraction; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D002264:Carboxylic Acids; D009284:Naphthols; D002110:Caffeine