Complex of a Lisuride Derivative and (S)-Naproxen

The structure of a complex between (+)-1-allylisuride and the (+)-(S) isomer of 2-(6-methoxy-2-naphthyl)propionic acid (naproxen), (+)-(5R,8S)-1-allyl-9,10-didehydro-8-(N′,N′)-diethylureido)-6-methylergolin-6-ium-2-(6-methoxy-2-naphthyl)propionate 2-(6-methoxy-2-naphthyl)propionic acid acetonitrile solvate hydrate, C₂₃H₃₁N₄O⁺.C₁₄H₁₃O₃⁻.₁₄H₁₄O₃.C₃H₈O.H₂O, has been determined. At the pH of the crystallization conditions, each molecule of allylisuride is protonated and interacts with two molecules of naproxen in a different modes; with one molecule a π-π interaction seems to occur between aromatic moieties, while with the other, which appears to be deprotonated, hydrogen bonds are present. The electrostatic interactions seem sensitive to the configuration at the asymmetric C atom of naproxen and are likely to be responsible for the enantio­discriminative process. In the asymmetric unit, one molecule of isopropyl alcohol and one of water are present. They are connected through a network of hydrogen bonds to the carbonyl group of allyllisuride and to the carboxyl groups of the two mol­ecules of naproxen.

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