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Powder X-ray diffraction of oseltamivir phosphate (Tamiflu®), C16H31N2O8P

Published online by Cambridge University Press:  03 June 2020

Ryan L. Hodge ,
James A. Kaduk Open the ORCID record for James A. Kaduk [Opens in a new window] ,
Amy M. Gindhart  and
Thomas N. Blanton Open the ORCID record for Thomas N. Blanton [Opens in a new window]
Ryan L. Hodge
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois60540, USA
James A. Kaduk*
Affiliation:
North Central College, 131 S. Loomis St., Naperville, Illinois60540, USA Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois60616, USA
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newton Square, Pennsylvania19073-3273, USA
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newton Square, Pennsylvania19073-3273, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of oseltamivir phosphate has been refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Oseltamivir phosphate crystallizes in space group P21212 (#18) with a = 24.0079(3), b = 24.6716(2), c = 7.45254(5) Å, V = 4414.24(5) Å3 at 295 K, and Z = 8. Prominent in the crystal structure are hydrogen bonds between the phosphate groups and the ammonium groups of the oseltamivir cations. The strong hydrogen bonds link the cations and the anions into columns parallel to the c-axis, with van der Waals interactions between the columns. Thermal expansion between 120 and 295 K is anisotropic. The powder pattern is included in the Powder Diffraction File™ as entry 00-068-1107.

Keywords

oseltamivir phosphateTamifluRietveld refinementdensity functional theory
Type
Data Report
Information
Powder Diffraction , Volume 35 , Issue 3 , September 2020 , pp. 216 - 218
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Copyright
Copyright © International Centre for Diffraction Data, 2020

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References

Gates-Rector, S. and Blanton, T. N. (2019). “The Powder Diffraction File: a quality materials characterization database,” Powd. Diff. 34(4), 352–260.CrossRefGoogle Scholar
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Naumov, P., Yasuda, N., Rabeh, W. M., and Bernstein, J. (2013). “The elusive crystal structure of the neuraminidase inhibitor Tamiflu (oseltamivir phosphate): molecular details of action,” Chem. Commun. 49, 1948–1950.CrossRefGoogle ScholarPubMed