Vibrational spectroscopic and supramolecular studies applied to a chloramphenicol derivative

Abstract

The crystal structure of the 4-{[(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl]oxy}-4-oxobutanoic acid (chloramphenicol succinate – CPS – C15H16Cl2N2O8) was analyzed by single-crystal X-ray diffraction, and the analysis was supported by vibrational spectroscopy (Raman and infrared). The spectral band assignments were assisted by DFT calculations. The chloramphenicol derivative showed significant homomeric synthons involving chains and dimers through conventional OH⋯O and NH⋯O hydrogen bonds, which were supported by the experimental infrared spectrum. Moreover, the role of non-conventional hydrogen bonds, such as CH⋯O, CH⋯π and π-π stacking, has also been analyzed by Full Interaction Maps.