Crystal structure of racemic chloramphenicol.

The racemic title compound {systematic name: 2,2-di-chloro-N-[(1R,2R)-1,3-dihy-droxy-1-(4-nitro-phen-yl)propan-2-yl]acetamide}, C11H12Cl2N2O5, crystallizes in the space group P1. In the crystal, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional architecture, enclosing R 2 2(14), R 2 2(12), R 2 2(10) and R 4 4(4) loops. The title compound complements the known ortho-rhom-bic form of natural (homochiral) chloramphenicol [Acharya et al. (1979 ▸). Acta Cryst. B35, 1360-1363], which crystallizes in space group C2221. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯O/O⋯H (39.4%), H⋯H (21.7%), H⋯C/C⋯H (15.5%) and Cl⋯C/C⋯Cl (8.3%) inter-actions.