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Powder X-ray diffraction of fluorometholone, C22H29FO4

Published online by Cambridge University Press:  27 March 2020

Diana Gonzalez ,
Joseph T. Golab ,
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]
Diana Gonzalez
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: kaduk@polycrystallography.com
Rights & Permissions [Opens in a new window]

Abstract

Commercial fluorometholone, CAS #426-13-1, crystallizes in the monoclinic space group P21 (#4) with a = 6.40648(2), b = 13.43260(5), c = 11.00060(8) Å, β = 92.8203(5)°, V = 945.517(5) Å3, and Z = 2. A reduced cell search in the Cambridge Structural Database yielded one previous structure determination, using single-crystal data at 292 K. In this work, the sample was ordered from the United States Pharmacopeial Convention (Lot # R032K0) 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 (DFT) techniques. Hydrogen positions were included as a part of the structure and were re-calculated during the refinement. The diffraction data were collected on beamline 11-BM at the Advanced Photon Source, Argonne National Laboratory, and the powder X-ray diffraction pattern of the compound has been submitted to ICDD® for inclusion in the Powder Diffraction File™. The agreement of the Rietveld-refined and DFT-optimized structures is excellent; the root-mean-square Cartesian displacement is 0.060 Å. In addition to the O–H⋯O hydrogen bonds observed by Park et al. (Park, Y. J., Lee, M. Y., and Cho, S. I. (1992). “Fluorometholone,” J. Korean Chem. Soc. 36, 812–817), C–H⋯O hydrogen bonds contribute to the crystal energy.

Keywords

fluorometholoneEfflumidex®X-ray diffractionPowder Diffraction File
Type
Data Report
Information
Powder Diffraction , Volume 35 , Issue 1 , March 2020 , pp. 71 - 72
Copyright
Copyright © International Centre for Diffraction Data 2020

Fluorometholone (brand names: Efflumidex, Flucon, FML Forte, and FML) is a prescription drug classified as a synthetic glucocorticoid used to treat optical inflammation or diseases. Commercial fluorometholone, CAS #426-13-1, crystallizes in the monoclinic space group P21 (#4) with a = 6.40648(2), b = 13.43260(5), c = 11.00060(8) Å, β = 92.8203(5)°, V = 945.517(5) Å3, and Z = 2. A reduced cell search in the Cambridge Structural Database (Groom et al., Reference Groom, Bruno, Lightfoot and Ward2016) yielded one previous structure determination (Park et al., Reference Park, Lee and Cho1992), using single-crystal data at 292 K.

In this work, the sample was ordered from the United States Pharmacopeial Convention (Lot # R032K0) and analyzed as-received. The diffraction data were collected on beamline 11-BM at the Advanced Photon Source, Argonne National Laboratory. The room temperature (295 K) crystal structure was refined using synchrotron (λ = 0.412826 Å) powder diffraction data and optimized using density functional theory (DFT) techniques. Hydrogen positions were included as a part of the structure and were re-calculated during the refinement (Figure 1).

Figure 1. Powder X-ray diffraction pattern of fluorometholone. The Rietveld-refined structure is indicated in red, and the DFT-optimized structure is indicated in blue.

The agreement of the Rietveld-refined and DFT-optimized structures is excellent; the root-mean-square Cartesian displacement is 0.060 Å. In addition to the O–H⋯O hydrogen bonds observed by Park et al. (Reference Park, Lee and Cho1992), C–H⋯O hydrogen bonds contribute to the crystal energy (Table I). The powder X-ray diffraction pattern of the compound has been submitted to ICDD® for inclusion in the Powder Diffraction File™.

TABLE I. Hydrogen bonds (CRYSTAL14) in fluorometholone.

a Correlation between overlap population and hydrogen bond energy not yet available for C–H⋯O hydrogen bonds.

b Intramolecular.

DEPOSITED DATA

CIF and/or RAW data files were deposited with ICDD. You may request this data from ICDD at .

ACKNOWLEDGEMENTS

The use of the Advanced Photon Source at Argonne National Laboratory was supported by the U.S. Department of Energy, Office of Science, and Office of Basic Energy Sciences under Contract No. DE-AC02-06CH11357. This work was partially supported by the International Centre for Diffraction Data.

References

Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. B. 72, 171–179.CrossRefGoogle ScholarPubMed
Park, Y. J., Lee, M. Y., and Cho, S. I. (1992). “Fluorometholone,” J. Korean Chem. Soc. 36, 812–817.Google Scholar
Figure 0

Figure 1. Powder X-ray diffraction pattern of fluorometholone. The Rietveld-refined structure is indicated in red, and the DFT-optimized structure is indicated in blue.

Figure 1

TABLE I. Hydrogen bonds (CRYSTAL14) in fluorometholone.