Date Published: March 01, 2012
Publisher: International Union of Crystallography
Author(s): Shuji Noguchi, Sadahiro Fujiki, Yasunori Iwao, Keiko Miura, Shigeru Itai.
In the crystal structure of the title compound, clarithromycin (CAM) monohydrate, C38H69NO13·H2O, the water molecule behaves as a proton donor and is hydrogen bonded to the hydroxy O atom of the CAM cladinose ring. The hydroxy O atom also behaves as a proton donor, forming an intermolecular hydrogen bond with one of the hydroxy groups of the 14-membered aglycone ring. The CAM molecules are linked through these hydrogen bonds into chains running parallel to the c axis.
For background to the title compound, see Avrutov et al. (2003 ▶); Noguchi, Fujiki et al. (2012 ▶). For information relating to the pharmaceutical properties of CAM, see: Yajima et al. (1999 ▶, 2002 ▶); Fujiki et al. (2011 ▶); Liu et al. (1999 ▶). For related structures, see: Noguchi, Miura et al. (2012 ▶; form I, anhydrate); Jin et al. (2011 ▶; form 0, ethanol solvate); Stephenson et al. (1997 ▶; form II, anhydrate); Liang & Yao (2008 ▶; form III, acetonitrile solvate); Parvez et al. (2000 ▶; hydrochloride salt); Iwasaki et al. (1993 ▶; methanol solvate).