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Crystal structure of cephalexin monohydrate, C16H17N3O4S(H2O)

Published online by Cambridge University Press:  03 November 2020

James A. KadukOpen the ORCID record for James A. Kaduk[Opens in a new window],
Amy M. Gindhart and
Thomas N. BlantonOpen the ORCID record for Thomas N. Blanton[Opens in a new window]
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, IL 60616, USANorth Central College, 131 S. Loomis St., Naperville, IL 60540, USA
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, PA 19073-3273, USA
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, PA 19073-3273, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: kaduk@polycrystallography.com
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Abstract

The crystal structure of cephalexin monohydrate has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Cephalexin monohydrate crystallizes in space group C2 (#5) with a = 27.32290(17), b = 11.92850(4), c = 16.75355(8) Å, β = 108.8661(4)°, V = 5166.99(3) Å3, and Z = 12. Although the general arrangement of molecules is similar to that in cephalexin dihydrate, the structural differences result in very different powder patterns. The crystal structure is characterized by alternating layers of hydrogen bonds and van der Waals contacts parallel to the bc-plane. The water molecules occur in clusters. Five of the six protons in the water molecules act as donors in O–H⋯O hydrogen bonds. The sixth hydrogen atom acts as a donor to two different phenyl ring carbon atoms to form bifurcated O–H⋯C hydrogen bonds. Each cephalexin molecule is a zwitterion, containing ammonium and carboxylate groups. The ammonium ions form N–H⋯O hydrogen bonds to carboxylate groups and water molecules, as well as to carbonyl groups. The powder pattern is included in the Powder Diffraction File™ as entry 00-065-1417.

Keywords

cephalexinpowder diffractionRietveld refinementdensity functional theory

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Type
New Diffraction Data
Information
Powder Diffraction , Volume 35 , Issue 4 , December 2020, pp. 293 - 300
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Copyright
Copyright © 2020 International Centre for Diffraction Data

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