Hostname: page-component-78c5997874-lj6df Total loading time: 0 Render date: 2024-11-17T19:05:34.809Z Has data issue: false hasContentIssue false

Powder X-ray diffraction of trimethoprim Form I, C14H18N4O3

Published online by Cambridge University Press:  06 February 2020

Jerry Hong
Affiliation:
Illinois Mathematics and Science Academy, 1500 Sullivan Rd., Aurora, Illinois60506-1000, USA
Joseph T. Golab
Affiliation:
Illinois Mathematics and Science Academy, 1500 Sullivan Rd., Aurora, Illinois60506-1000, USA
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois60616, USA North Central College, 131 S. Loomis St., Naperville, Illinois60540, USA
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania19073-3273, USA
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania19073-3273, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]

Abstract

Trimethoprim crystallizes in the triclinic space group P-1 (#2) with a = 10.5085(3), b = 10.5417(2), c = 8.05869(13) Å, α = 101.23371(21), β = 112.1787(3), γ = 112.6321(4)°, V = 743.729 Å3, and Z = 2. A reduced cell search in the Cambridge Structural Database yielded three previous structure determinations, using data collected at 100 K, 173 K, and room temperature. In this work, the sample was ordered from the United States Pharmacopeial Convention (USP) and analyzed as-received. The room temperature (295 K) crystal structure was refined using synchrotron (λ = 0.412826 Å) powder diffraction data and optimized using density functional theory techniques. We found similar hydrogen bonding patterns with the previous determinations. In addition, we identified two C–H⋯O hydrogen bonds, which also contribute to the crystal energy. When comparing the previously reported trimethoprim structure determinations, the unit cell length lattice parameters were found to contract at lower temperatures, particularly 100 K. All structures show reasonable agreement, with unit cell length differences ranging between 0.05 and 0.15 Å. The diffraction data for this study were collected on beamline 11-BM at the Advanced Photon Source, and the powder X-ray diffraction pattern of the compound has been submitted to ICDD® for inclusion in the Powder Diffraction File™ (PDF®).

Type
Data Report
Copyright
Copyright © International Centre for Diffraction Data 2020

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Gates-Rector, S. and Blanton, T. (2019). “The Powder Diffraction File: a quality materials characterization database,” Powder Diffr. 34(4), 352360.CrossRefGoogle Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. B. 72, 171179.CrossRefGoogle ScholarPubMed
Kaduk, J. A., Crowder, C. E., Zhong, K., Fawcett, T. G., and Suchomel, M. R. (2014). “Crystal structure of atomoxetine hydrochloride (Strattera), C17H22NOCl,” Powder Diffr. 29(3), 269273.CrossRefGoogle Scholar
Koetzle, T. F. and Williams, G. J. B. (1976). “The crystal and molecular structure of the antifolate drug trimethoprim (2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine),” J. Am. Chem. Soc. 98, 20742078.CrossRefGoogle Scholar
Maddileti, D., Swapna, B., and Nangia, A. (2015). “Tetramorphs of the antibiotic drug trimethoprim: characterization and stability,” Cryst. Growth Des. 15, 17451746.CrossRefGoogle Scholar
Rauf, K. and Bolte, M. (2006). CSD Communication; Refcode AMXBPM11.Google Scholar