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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 5, Number 4
April 20, 1984 

The Crystal and Molecular Structure of Chloramphenicol Base
Whanchul Shin, Myungho Pyo
The crystal structure of chloramphenicol base, C9Hl2N2O4, the deacylated base of antibiotic chloramphenicol, has been determined by X-ray diffraction techniques using diffractometer data obtained by the ω-2θ scan technique with CuKα radiation from a crystal with space group symmetry P212121, and unit cell parameters a = 22.322(6), b = 7.535(6), c = 5.781(5) Å. The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.051 for the 573 observed reflections. The overall conformation of the base is quite different from those of the chloramphenicol congeners which are similar dcspite the presence of many rotatable single bonds. The propane chain in the base is bent with respect to the phenyl ring, while it is extended in the chloramphenicol congeners. There is no intramolecular hydrogen bond between the hydroxyl groups of the propanediol moiety. All of the molecules in the crystal lattice are connected by a three-dimensional hydrogen bonding network.
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