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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 4, Number 2
February 20, 1983 

The Crystal and Molecular Structure of Thiamphenicol
Whanchul Shin, Sangsoo Kim
The structure of thiamphenicol, one of the congeners of chloramphenicol which is a well-known antibiotic, has been determined by single crystal x-ray diffraction techniques. The crystal structure was determined using diffractometer data obtained by the 2θ: ω scan technique with MoKα radiation from a crystal having space group symmetry P212121, and unit cell parameters a = 5.779, b = 15.292 and c = 17.322 Å . The structure was solved by direct methods and refined by least squares to an R = 0.070 for the 2116 reflections. The overall V-shaped conformation of thiamphenicol revealed in this study is consistent with those from the crystallographic studies and the proposed models from the theoretical and nmr studies of chloramphenicol. However there is no intramolecular hydrogen bond and the propanediol moiety is fully extended in the thiamphenicol molecule, while the crystal structures of chloramphenicol show the existence of the hydrogen bond between the two hydroxyl groups of the propanediol moiety forming an acyclic ring. All of the thiamphenicol molecules in the crystal are linked by a threedimensional hydrogen bonding network.
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