The title compound {systematic name: [2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl)ethyl]dimethylammonium 3-carboxypropanoate monohydrate}, C(16)H(26)NO(2)(+) x C(4)H(5)O(4)(-) x H(2)O, is a succinate salt of O-desmethylvenlafaxine (desvenlafaxine). The present structure is one of four reported polymorphs of this salt, which is a new antidepressant drug. The carboxyl group of the succinate anion adopts a rare anti conformation and is engaged in a very short O-H...O(-) hydrogen-bond contact. Both cations and anions are involved separately in the formation of distinct O-H...O hydrogen-bonded networks. Desvenlafaxine cations and water molecules self-assemble to generate a honeycomb layer, while the succinate anions form a linear tape structure. These hydrogen-bonded networks are interlinked via N-H...O and O-H...O hydrogen bonds. The hydrogen-bonding network is so strong that desolvation and melting occur together at approximately 402 K. Thus, the crystal structure may be used to understand the thermal stability and solubility of the compound at the molecular level.

The title compound, C(8)H(17)NO(2), exists as a zwitterion, adopting a propeller conformation. Molecules self-assemble to form a hydrogen-bonded layer parallel to the ab crystallographic plane connected by N+-H...O- and C-H...O- hydrogen bonds. These layers are stacked along the c axis and are stabilized by van der Waals interactions.

Attempts to synthesize the antidepressant drug atomoxetine directly by p-TSA-catalyzed reaction between o-cresol and N-methyl-3-phenyl-3-hydroxypropyl amine in toluene at reflux temperature surprisingly resulted in the formation of ortho-substituted phenol derivative. The structure is unambiguously confirmed by single crystal X-ray.

Polyphenylalkane derivatives Q 0720Unusual p-Toluene Sulfonic Acid-Catalyzed Carbon-Carbon Bond Formation.-An unusual C-C bond formation is reported for the reaction of amine (I) with o-cresol (II) in the presence of Tos-OH as catalyst for the first time. The structure of the unexpected product (III) (no yield given) is confirmed by X-ray analysis. -(GOVINDAN, S.; MADDIPATLA, M.; PODICHETTY, A. K.; MACHARLA, P.; NALIVELA, V.; SUNDARAM, V.; MATHAD, V. T.; GHANTA*, M. R.; YALAVARTI, R. K.; Synth. Commun. 35 (2005) 13, 1765-1768; Dep. Res. Dev., Dr. Reddy's Lab. Ltd., Bollaram, Jinnaram 502 325, India; Eng.) -H. Haber 46-088