Weak C-H···X (X = O, N) hydrogen bonds in the crystal structure of dihydroberberine.

ABSTRACT: Dihydroberberine (systematic name: 9,10-dimethoxy-6,8-dihydro-5H-1,3-dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline), C20H19NO4, a reduced form of pharmacologically important berberine, crystallizes from ethanol without interstitial solvent. The molecule shows a dihedral angle of 27.94 (5)° between the two arene rings at the ends of the molecule, owing to the partial saturation of the inner quinolizine ring system. Although lacking classical O-H or N-H donors, the packing in the crystalline state is clearly governed by C-H···N and C-H···O hydrogen bonds involving the two acetal-type C-H bonds of the 1,3-dioxole ring. Each dihydroberberine molecule is engaged in four hydrogen bonds with neighbouring molecules, twice as donor and twice as acceptor, thus forming a two-dimensional sheet network

SUBMITTER: Pingali S 

PROVIDER: S-EPMC4165590 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature