Two ortho-rhom-bic polymorphs of hydro-morphone

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 72; no. Pt 5; pp. 730 - 733
• Main Authors: Mazurek, Jaroslaw, Hoffmann, Marcel, Fernandez Casares, Ana, Cox, D Phillip, Minardi, Mathew D, Sasine, Josh
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01.05.2016
• Subjects: Research Communications; crystal structure; hydro­morphone,hydrogen bonding; polymorphism
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989016006563

Conditions to obtain two polymorphic forms by crystallization from solution were determined for the analgesic drug hydro-morphone [C17H19NO3; systematic name: (4R,4aR,7aR,12bS)-9-hy-droxy-3-methyl-1,2,4,4a,5,6,7a,13-octa-hydro-4,12-methano-benzofuro[3,2-e]iso-quinolin-7-one]. These two crystalline forms, designated as I and II, belong to the P212121 ortho-rhom-bic space group. In both polymorphs, the hydro-morphone mol-ecules adopt very similar conformations with some small differences observed only in the N-methyl amine part of the mol-ecule. The crystal structures of both polymorphs feature chains of mol-ecules connected by hydrogen bonds; however, in form I this inter-action occurs between the hydroxyl group and the tertiary amine N atom whereas in form II the hydroxyl group acts as a donor of a hydrogen bond to the O atom from the cyclic ether part.