Powder X-ray study of racemic (2RS,3RS)-5-amino-3-[4-(3-methoxyphenyl)piperazin-1-yl]-1,2,3,4-tetrahydronaphthalen-2-ol.

Abstract

The structure of the title benzovesamicol analogue, C(21)H(27)N(3)O(2), an important compound for the diagnosis of Alzheimer's disease, has been determined by X-ray powder diffraction. The title compound was firstly synthesized and characterized by spectroscopic methods (FT-IR, and (13)C and (1)H NMR). The compound is a racemic mixture of enantiomers which crystallizes in the monoclinic system in a centrosymmetric space group (P2(1)/c). Crystallography, in particular powder X-ray diffraction, was pivotal in revealing that the enantio-resolution did not succeed. The piperazine ring is in a chair conformation, while the cyclohexene ring assumes a half-chair conformation. The crystal packing is dominated by intermolecular O-H···N hydrogen bonding which links molecules along the c direction.

• Authors: Thaer Assaad, Mwaffak Rukiah
• Journal: Acta crystallographica. Section C, Crystal structure communications (Acta Crystallogr C) Vol. 67 Issue Pt 11 Pg. o469-72 (Nov 2011) ISSN: 1600-5759 [Electronic] United States
• PMID: 22051965 (Publication Type: Journal Article)

Chemical References

• (2RS,3RS)-5-amino-3-(4-(3-methoxyphenyl)piperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-ol
• Cyclohexenes
• Phthalic Acids
• Piperazines

Topics

• Crystallography, X-Ray
• Cyclohexenes (chemistry)
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Molecular Structure
• Phthalic Acids (chemistry)
• Piperazines (chemistry)
• Stereoisomerism
• X-Ray Diffraction