Erythromycin A dimethyl sulfoxide disolvate 1.43-hydrate

Jürgen Brüning,Jan W Bats,Tanja K Trepte,Martin U Schmidt

doi:10.1107/s1600536812005223

Jürgen Brüning, Jan W Bats + Show 2 more

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https://doi.org/10.1107/s1600536812005223

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Abstract

The title compound, C37H67NO13·2C2H6OS·1.43H2O, is a macrolide antibiotic with better solubility and better dermal penetration abilities than erythromycin A itself. The asymmetric unit of this form contains one erythromycin A molecule, two dimethyl sulfoxide (DMSO) solvent molecules, a fully occupied water molecule and a partially occupied water molecule with an occupancy factor of 0.432 (11). The 14-membered ring of the erythronolide fragment has a conformation which differs considerably from that in erythromycin A dihydrate [Stephenson, Stowell, Toma, Pfeiffer & Byrn (1997 ▶). J. Pharm. Sci. 86, 1239–1244]. One of the two DMSO molecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water molecule. In the crystal, erythromycin molecules are connected by O—H⋯O hydrogen bonds involving the hydroxy groups and the fully occupied water molecule to form layers parallel to (010). These layers are connected along the b-axis direction only by a possible hydrogen-bonding contact involving the partially occupied water molecule.

Highlights

The title compound, C37H67NO132C2H6OS1.43H2O, is a macrolide antibiotic with better solubility and better dermal penetration abilities than erythromycin A itself
Molecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water molecule
Erythromycin molecules are connected by O—H O hydrogen bonds involving the hydroxy groups and the fully occupied water molecule to form layers parallel to (010)

Summary

Crystal data

The asymmetric unit of this form contains one erythromycin A molecule, two dimethyl sulfoxide (DMSO) solvent molecules, a fully occupied water molecule and a partially occupied water molecule with an occupancy factor of 0.432 (11). One of the two DMSO molecules is disordered over two orientations; the orientation depends on the presence or absence of the second, partially occupied, water molecule. Erythromycin molecules are connected by O—H O hydrogen bonds involving the hydroxy groups and the fully occupied water molecule to form layers parallel to (010). These layers are connected along the b-axis direction only by a possible hydrogen-bonding contact involving the partially occupied water molecule

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