Blanton, Thomas N.

Gindhart, Amy M.

Golab, Joseph T.

Gonzalez, Diana, \u2720

Kaduk, James A.

English

Illinois Mathematics and Science Academy: DigitalCommons@IMSA

DATA REPORTPowder X-ray diffraction of fluorometholone, C22H29FO4Diana Gonzalez,1 Joseph T. Golab,1 James A. Kaduk ,2,3,a) Amy M. Gindhart,4 andThomas N. Blanton 41Illinois Mathematics and Science Academy, 1500 Sullivan Rd., Aurora, Illinois 60506-1000, USA2Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616, USA3North Central College, 131 S. Loomis St., Naperville, Illinois 60540, USA4ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273, USA(Received 29 November 2019; accepted 10 December 2019)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, andZ = 2. A reduced cell search in the Cambridge Structural Database yielded one previous structuredetermination, using single-crystal data at 292 K. In this work, the sample was ordered from theUnited States Pharmacopeial Convention (Lot # R032K0) and analyzed as-received. The room tem-perature (295 K) crystal structure was refined using synchrotron (λ = 0.412826 Å) powder diffractiondata and optimized using density functional theory (DFT) techniques. Hydrogen positions wereincluded as a part of the structure and were re-calculated during the refinement. The diffractiondata were collected on beamline 11-BM at the Advanced Photon Source, Argonne NationalLaboratory, and the powder X-ray diffraction pattern of the compound has been submitted toICDD® for inclusion in the Powder Diffraction File™. The agreement of the Rietveld-refined andDFT-optimized structures is excellent; the root-mean-square Cartesian displacement is 0.060 Å. Inaddition to the O–H⋯O hydrogen bonds observed by Park et al. (Park, Y. J., Lee, M. Y., andCho, S. I. (1992). “Fluorometholone,” J. Korean Chem. Soc. 36, 812–817), C–H⋯O hydrogenbonds contribute to the crystal energy. © 2020 International Centre for Diffraction Data.[doi:10.1017/S0885715619000915]Key words: fluorometholone, Efflumidex®, X-ray diffraction, Powder Diffraction FileFluorometholone (brand names: Efflumidex, Flucon,FML Forte, and FML) is a prescription drug classified as asynthetic glucocorticoid used to treat optical inflammation ordiseases. Commercial fluorometholone, CAS #426-13-1, crys-tallizes 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 inthe Cambridge Structural Database (Groom et al., 2016)yielded one previous structure determination (Park et al.,1992), using single-crystal data at 292 K.In this work, the sample was ordered from the UnitedStates Pharmacopeial Convention (Lot # R032K0) and ana-lyzed as-received. The diffraction data were collected onbeamline 11-BM at the Advanced Photon Source, ArgonneNational Laboratory. The room temperature (295 K) crystalstructure was refined using synchrotron (λ = 0.412826 Å)powder diffraction data and optimized using density func-tional theory (DFT) techniques. Hydrogen positions wereincluded as a part of the structure and were re-calculated dur-ing the refinement (Figure 1).The agreement of the Rietveld-refined and DFT-opti-mized structures is excellent; the root-mean-square Cartesiandisplacement is 0.060 Å. In addition to the O–H⋯O hydrogenbonds observed by Park et al. (1992), C–H⋯O hydrogenbonds contribute to the crystal energy (Table I). The powderX-ray diffraction pattern of the compound has been submittedto ICDD® for inclusion in the Powder Diffraction File™.DEPOSITED DATACIF and/or RAW data files were deposited with ICDD.You may request this data from ICDD at info@icdd.com.ACKNOWLEDGEMENTSThe use of the Advanced Photon Source at ArgonneNational Laboratory was supported by the U.S. Departmentof Energy, Office of Science, and Office of Basic EnergySciences under Contract No. DE-AC02-06CH11357. Thiswork was partially supported by the International Centre forDiffraction Data.Groom,, C. R., Bruno,, I. J., Lightfoot, M. P., and Ward,, S. C. (2016). “TheCambridge Structural Database,” Acta Crystallogr. B. 72, 171–179.Park,, Y. J., Lee,, M. Y., and Cho,, S. I. (1992). “Fluorometholone,” J. KoreanChem. Soc. 36, 812–817.a)Author to whom correspondence should be addressed. Electronic mail:kaduk@polycrystallography.com71 Powder Diffraction 35 (1), March 2020 0885-7156/2020/35(1)/71/2/$18.00 © 2020 JCPDS-ICDD 71brought to you by COREView metadata, citation and similar papers at core.ac.ukprovided by Illinois Mathematics and Science Academy: DigitalCommons@IMSATABLE I. Hydrogen bonds (CRYSTAL14) in fluorometholone.H-bond D–H (Å) H⋯A (Å) D⋯A (Å) D–H⋯A (°) Overlap (e) E (kcal mol−1)O3–H29⋯O1 0.980 1.784 2.753 169.1 0.050 12.2O2–H28⋯O3 0.979 1.892 2.835 160.7 0.059 13.3C22–H27⋯O4 1.094 2.599 3.686 172.5 0.012 aC21–H23⋯O1 1.096 2.525 3.567 158.5 0.017 aC16–H14⋯O4 1.091 2.387b 2.840 103.1 0.014 aC1–H1⋯O4 1.087 2.515 3.598 173.4 0.020 aaCorrelation between overlap population and hydrogen bond energy not yet available for C–H⋯O hydrogen bonds.bIntramolecular.Figure 1. Powder X-ray diffraction pattern of fluorometholone. The Rietveld-refined structure is indicated in red, and the DFT-optimized structure is indicated inblue.72 Powder Diffr., Vol. 35, No. 1, March 2020 Gonzalez et al. 72

Powder X-ray diffraction of fluorometholone, C22H29FO4

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Powder X-ray diffraction of fluorometholone, C22H29FO4

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