Powder X-ray study of racemic (2RS,3RS)-5-amino-3-(4-phenylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalen-2-ol

Abstract

The title compound, C(20)H(25)N(3)O, an important precursor for the preparation of benzovesamicol analogues for the diagnosis of Alzheimer's disease, has been synthesized and characterized by FT-IR, and (1)H and (13)C NMR spectroscopic analyses. The crystal structure was analysed using powder diffraction as no suitable single crystal was obtained. The piperazine ring has a chair conformation, while the cyclohexene ring assumes a half-chair conformation. The crystal packing is mediated by weak contacts, principally by complementary intermolecular N-H···O hydrogen bonds that connect successive molecules into a chain. Further stabilization is provided by weak C-H···N contacts and by a weak intermolecular C-H···π interaction.

Conformations and Vibrational Frequencies of a Precursor of Benzovesamicol Analogues Studied by Density Functional Theories

“…Thus, of all the methods tested, the LSDA method has the least RMSD between the calculated coordinates of the gas phase and experimental set-up (powder). 9 As shown in Table S1, differences exist between the calculated and X-ray parameters because experimental values were obtained from molecules in solid powder state, whereas theoretical values were based on an isolated molecule in gas phase.…”