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Crystal structure of vardenafil hydrochloride trihydrate, C23H33N6O4SCl (H2O)3

Published online by Cambridge University Press:  04 October 2018

Austin M. Wheatley ,
James A. Kaduk Open the ORCID record for James A. Kaduk [Opens in a new window] ,
Amy M. Gindhart  and
Thomas N. Blanton
Austin M. Wheatley
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois 60540
James A. Kaduk*
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois 60540 Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of vardenafil hydrochloride trihydrate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Vardenafil hydrochloride trihydrate crystallizes in space group C2/c (#15) with a = 34.78347(16), b = 11.56752(4), c = 14.69308(5) Å, β = 93.3410(4), V = 5901.839(30) Å3, and Z = 8. The fused ring system and the phenyl ring are nearly co-planar; the interplanar angle between them is 6.0°. Two intramolecular hydrogen bonds help determine this conformation. These planes stack along the c-axis. The side chains of these ring systems have a large Uiso and are neighbors in the stacks. Along the a-axis, these stacks are separated by hydrophilic layers of chloride, water molecules, and the positively charged nitrogen atoms of the vardenafil cation. Hydrogen bonds are prominent in the crystal structure. The protonated nitrogen atom forms a strong hydrogen bond to the chloride anion. The water molecules form a hexagon, making hydrogen bonds with themselves, as well as the C1 and a ring nitrogen atom. These discrete hydrogen bonds form a cluster, and there is no extended hydrogen bond network. There are many C–H⋯Cl, C–H⋯O, and C–H⋯N hydrogen bonds, which (although individually weak) contribute significantly to the crystal energy. The powder pattern is included in the Powder Diffraction File™ as entry 00-066-1620.

Keywords

vardenafil hydrochloride trihydrateLevitra®powder diffractionRietveld refinementdensity functional theory
Type
New Diffraction Data
Information
Powder Diffraction , Volume 33 , Issue 4 , December 2018 , pp. 319 - 326
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Copyright
Copyright © International Centre for Diffraction Data 2018 

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