Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 4 (April 2014)

organic compounds

fn3163 scheme

Acta Cryst. (2014). C70, 388-391    [ doi:10.1107/S2053229614003751 ]

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

S. Pingali, J. P. Donahue and F. Payton-Stewart

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 that lies parallel to the (100) plane.

CCDC reference: 987722

Formula: C20H19NO4

Keywords: crystal structure; hydrogen bonding; di­hydro­berberine; berberine derivative; biological activity.

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[ doi:10.1107/S2053229614003751/fn3163Isup3.cml ]
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