Acta Crystallographica Section B

Structural Science

Volume 56, Part 6 (December 2000)

research papers

Acta Cryst. (2000). B56, 1094-1102 [ doi:10.1107/S0108768100012805 ]

Selective solvent inclusion as a tool for mapping molecular properties in crystal structures: a diethylstilbestrol example

C. H. Görbitz and H.-P. Hersleth

Abstract: Useful information about hydrogen bonding, the preferred modes of hydrophobic interaction and conformational preferences of a specific molecule can be obtained from cocrystallization of the solute with a selected series of solvent molecules. This method is used in a study of nine different crystal structures of diethylstilbestrol (DES) solvates. It is shown that solvent inclusion results not only in stronger hydrogen bonds, but usually also in a larger number of favorable C-H [pi] interactions between DES molecules. Furthermore, solvent molecules such as DMSO, DMF, acetonitrile and acetone demonstrate important hydrogen-bond donating properties in addition to their more familiar role as hydrogen-bond acceptors. Molecular conformations in the crystal structures compare favorably with results from molecular mechanics calculations.

Keywords: Solvent; Inclusion; Diethylstilbestrol; Hydrogen bonding; Conformation.