(2R*,4S*)-2-(Pyridin-3-yl)-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol: a three-dimensional framework built from O—H...N, C—H...O and C—H...π(arene) hydrogen bonds

Abstract

The title compound, C 15 H 16 N 2 O, crystallizes in the space group P2 1 2 1 2 1 with Z 0 = 1. The seven-membered ring adopts a chair-type conformation with the hydroxy and pyridyl substituents in equatorial sites. Molecules are linked into a three-dimensional framework structure by a combination of O-HÁ Á ÁN, C-HÁ Á ÁO and C-HÁ Á Á(arene) hydrogen bonds, but N-HÁ Á ÁO and N-HÁ Á Á(arene) interactions are absent from the structure. Comparisons are made with some related compounds.

Crystal structures of five new substituted tetrahydro-1-benzazepines with potential antiparasitic activity

“…A simple synthetic approach for the stereoselective synthesis of exo-2-aryl-1,4epoxytetrahydro-1-benzazepines and the alcohol derivatives exo-2-aryl-1,4-tetrahydro-1-benzazepin-4-ols, through the selective oxidation of substituted ortho-allyl-N-benzylanilines and subsequent intramolecular 1,3-dipolar cycloaddition of the formed nitrones and posterior opening of the epoxide, was described (Gó mez-Ayala et al, 2006; Acosta, Palma & Bahsas, ISSN 2053ISSN -2296 # 2016 International Union of Crystallography 2010; Acosta et al, 2012) and applied systematically to prepare new compounds in the search for molecules with better biological activity against these parasites. Part of this systematic study of particularly active molecules (Acosta et al, 2008(Acosta et al, , 2009Gó mez et al, 2008Gó mez et al, , 2009Gó mez et al, , 2011Sanabría et al, 2010Sanabría et al, , 2014Blanco et al, 2012a,b,c;Yé pes et al, 2012Yé pes et al, , 2013Guerrero et al, 2014) included the crystal structure determination. Two series of structures are presented in this paper and their conformation and packing are described and compared.…”