Molecular Structure of a Chromatographic Chiral Selector Based on a Terguride Derivative

Abstract

The structure of (+)1-(3-allylpropyl)-(5R,8S,10R)-N,N-diethyl-N′-[6-methylergolin-8-yl]urea, C22H33N4O (allyl-terguride), has been determined as part of a study on the chiral recognition mechanism of ergot alkaloids when they are used as the chiral stationary phase for the separation of racemic mixtures in liquid chromatographic methods. At the pH of the solution used for the crystallization, the molecules of allyl-terguride are protonated at N(6). All bond distances and angles are in the expected ranges. In the asymmetric unit one hydroxide ion is present. Hydrogen bonds join molecules of allyl-terguride in pairs along the b axis, connecting O(2) of the hydroxide ion to O(1) of one molecule and to N(2) and N(6) of another.