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Powder X-ray diffraction of capecitabine, C15H22FN3O6

Published online by Cambridge University Press:  11 July 2019

James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616 North Central College, 131 S. Loomis St., Naperville, Illinois 60540
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].

Abstract

Capecitabine (Xeloda) is a chemotherapy drug used to treat breast, gastric, and colorectal cancers. Commercial capecitabine crystallizes in the orthorhombic space group P212121 (#19) with a = 5.20587(3), b = 9.52324(4), c = 34.79574(21) Å, V = 1725.062(12) Å3, and Z = 4. A reduced cell search in the Cambridge Structural Database (Groom C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016) Crystallogr. Sect. B: Struct. Sci., Cryst. Eng. Mater.72, 171–179) yielded three previous structure determinations (Rohlicek, J., Husak, M., Gavenda, A., Jegorov, A., Kratochvil, B., and Fitch, A. (2016). Acta Cryst. Sect. E: Crystallgr. Commun.72, 879–880, BOVDUM; Malińska, M., Krzeczyński, P., Czerniec-Michalik, E., Trzcińska, K., Cmoch, P., Kutner, A., and Woźniak, K. (2014). J. Pharm. Sci.103, 587–593, BOVDUM01 and BOVDUM02), using synchrotron powder data and later single crystal data at two temperatures. In this work, the sample was ordered from United States Pharmacopeial Convention (lot # G0J205), and analyzed as-received. The room temperature (295 K) crystal structure was refined using synchrotron (λ = 0.413914 Å) powder diffraction data, density functional theory (DFT), and Rietveld refinement techniques. Hydrogen positions were included as part of the structure, and were re-calculated during the refinement. The diffraction data were collected on a beamline 11-BM at the Advanced Photon Source, Argonne National Laboratory and the powder X-ray diffraction pattern of the compound is provided. The agreement of the Rietveld-refined and DFT-optimized structures is poorest in the pentyl side chain, consistent with the disorder observed previously.

Type
Data Report
Copyright
Copyright © International Centre for Diffraction Data 2019 

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Footnotes

*

Figure 1 has been corrected. A correction notice detailing this change has also been published (doi:10.1017/S0885715619000642).

References

Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. Sect. B: Struct. Sci., Cryst. Eng. Mater. 72, 171179.Google Scholar
Malińska, M., Krzeczyński, P., Czerniec-Michalik, E., Trzcińska, K., Cmoch, P., Kutner, A., and Woźniak, K. (2014). “Crystal structure and tautomerism of capecitabine,” J. Pharm. Sci. 103, 587593.Google Scholar
Rohlicek, J., Husak, M., Gavenda, A., Jegorov, A., Kratochvil, B., and Fitch, A. (2016). “Capecitabine from X-ray powder synchrotron data. Corrigendum,” Acta Cryst. Sect. E: Crystallgr. Commun. 72, 879880.Google Scholar
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