Selective solvent inclusion as a tool for mapping molecular properties in crystal structures: a diethylstilbestrol example.
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.
Görbitz
C H
CH
Department of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway. c.h.gorbitz@kjemi.uio.no
Hersleth
H P
HP
D000096:Acetone; D000097:Acetonitriles; D018360:Crystallography, X-Ray; D004054:Diethylstilbestrol / Q000737:chemistry*; D004121:Dimethyl Sulfoxide; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents
D000097:Acetonitriles; D012997:Solvents; D000096:Acetone; D004054:Diethylstilbestrol; D004121:Dimethyl Sulfoxide; C032159:acetonitrile