Weak C-H···X (X = O, N) hydrogen bonds in the crystal structure of dihydroberberine.
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.
Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, Box 114, New Orleans, LA 70125, USA.
Subramanya
S
Pingali
Department of Chemistry, Tulane University, 6400 Freret Street, New Orleans, LA 70118-5698, USA.
James P
JP
Donahue
Department of Chemistry, Xavier University of Louisiana, 1 Drexel Drive, Box 114, New Orleans, LA 70125, USA.
Florastina
F
Payton-Stewart
D001599:Berberine / Q000031:analogs & derivatives* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D012997:Solvents / Q000737:chemistry*
D012997:Solvents; D001599:Berberine; C039639:dihydroberberine
berberine derivative; biological activity; crystal structure; dihydroberberine; hydrogen bonding