High Resolution Structure of Half-Cage Isodrin Propionate, a Molecule Suitable for Studying Nuclear Overhauser Effects in the Organic Laboratory

Abstract

The nuclear overhauser effect (NOE) has emerged as a useful tool for studying the structural features of a molecule via NMR spectroscopy. Herein we describe the high quality solid state structure of half-cage isodrin propionate, whose facile synthesis makes it a suitable molecule to measure and study the NOE in both undergraduate and graduate organic laboratories. Half-cage isodrin propionate crystallizes in the monoclinic space group P2 ₁ /n with unit cell parameters a = 12.0064(11) Å, b = 12.7511(12) Å, c = 22.540(2) Å and β = 105.27(3)°. The asymmetric unit contains two Half-cage isodrin propionate molecules with atoms on general positions. Critical to the observation of NOE in the title molecule is an ultrashort interatomic contact involving two isolated, neighboring hydrogen atoms found in each half-cage molecule of the asymmetric unit. The interatomic distances were measured at 1.737(2) Å within the first half-cage molecule and 1.725(2) Å within the second. Secondary to the observation of these short interatomic separations, the solid state structure of half-cage isodrin propionate, with its Z’ > 1, represents a situation where each molecule’s inherent differences might be analyzed and discussed.

Graphical Abstract