Crystal and molecular structure and absolute configuration of lincomycin hydrochloride monohydrate

Lincomycin is a broad-spectrum antibiotic synthesized by Streptomyces lincolnensis that is particularly active against Gram-positive bacteria. It is widely used in human and veterinary applications. The crystal structure of lincomycin has been undertaken with a view to obtain the conformational and structural features of the drug in order to afford a comparison of its structural features with other aminoglycoside antibiotics. We report here the details of its structural and conformational features as determined by single-crystal X-ray crystallography. Crystals of lincomycin hydrochloride are orthorhombic, space group P2(1)2(1)2, with the cell dimensions a=18.5294(3) Angstroms, b=20.5980(4) Angstroms, c=6.17380(10) Angstroms, V=2356.35(7) Angstroms3. The structure was solved using X-ray diffraction data and refined to a final R-value of 0.0391 for 2321 reflections (I > or = 2sigma). The absolute configuration was established using the anomalous dispersion of the sulfur and chlorine atoms in the structure. The molecule consists of an amino acid linked by an amide group to a monosaccharide of galactose stereochemistry. A network of hydrogen-bonds stabilizes the crystal structure.