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Powder X-ray diffraction of escitalopram oxalate oxalic acid hydrate, (C20H21FN2O)2(C2O4)(H2C2O4)(H2O)0.16

Published online by Cambridge University Press:  19 January 2021

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]
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616, USA North Central College, 131 S. Loomis St., Naperville, Illinois 60540, USA
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273, USA
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: kaduk@polycrystallography.com

Abstract

Commercial escitalopram oxalate crystallizes as a hydrated adduct with oxalic acid, in the space group P21 with a = 8.029897(21), b = 25.09397(6), c = 11.138930(31) Å, β = 106.7759(2)°, V = 2148.992(7) Å3, and Z = 4. The agreement of the Rietveld and previous single-crystal structures is excellent; the root-mean-square Cartesian displacements of the non-H atoms of the two independent cations are 0.076 and 0.067 Å, respectively. The water molecule refined to a slightly different position and occupancy. The pattern is included in the Powder Diffraction File™ (PDF®) as entry 00-064-1507.

Keywords

excitolopramX-ray diffractionPowder Diffraction File

Information

Type
Data Report
Information
Powder Diffraction , Volume 36 , Issue 1 , March 2021 , pp. 68 - 69
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Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

I.

Escitalopram oxalate (Lexapro) is approved by the FDA for the treatment of depression and anxiety disorders. Commercial escitalopram oxalate crystallizes as a hydrated adduct with oxalic acid, in the space group P21 with a = 8.029897(21), b = 25.09397(6), c = 11.138930(31) Å, β = 106.7759(2)°, V = 2148.992(7) Å3, and Z = 4. A reduced cell search in the Cambridge Structural Database (Groom et al., Reference Groom, Bruno, Lightfoot and Ward2016) yielded the crystal structure of the (H2O)0.25 hydrate (de Diego et al., Reference de Diego, Bond and Dancer2011; Refcode WASGAA). In this work, the sample was ordered from Sigma-Aldrich (Lot #053M4712V) and analyzed as-received. The crystal structure at room temperature (295 K) was refined using synchrotron (λ = 0.413891 Å) powder diffraction data and Rietveld refinement techniques. The diffraction data were collected at beamline 11-BM at the Advanced Photon Source, Argonne National Laboratory. Figure 1 shows the powder X-ray diffraction pattern and the molecular structure. The agreement of the Rietveld and single-crystal structures is excellent; the root-mean-square Cartesian displacements of the non-H atoms of the two independent cations are 0.076 and 0.067 Å, respectively. The water molecule refined to a slightly different position and occupancy. The pattern is included in the Powder Diffraction File™ (PDF®) as entry 00-064-1507 (Gates-Rector and Blanton, Reference Gates-Rector and Blanton2019).

Figure 1.

Powder X-ray diffraction pattern of escitalopram oxalate oxalic acid hydrate, with the molecular structure.

ACKNOWLEDGEMENTS

The use of the Advanced Photon Source at Argonne National Laboratory was supported by the U. S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Contract No. DE-AC02-06CH11357. This work was partially supported by the International Centre for Diffraction Data. We thank Lynn Ribaud and Saul Lapidus for their assistance in the data collection.

DEPOSITED DATA

The supplementary material for this article, which includes Crystallographic Information Framework (CIF) files containing the results of the Rietveld refinement (including the raw data) was deposited with the ICDD. The data can be requested at .

References

de Diego, H. L., Bond, A. D., and Dancer, R. J. (2011). “Formation of solid solutions between racemic and enantiomeric citolopram oxalate,” Chirality 23, 408–416.CrossRefGoogle Scholar
Gates-Rector, S. D. and Blanton, T. N. (2019). “The Powder Diffraction File: a quality materials characterization database,” Powder Diffr. 34, 352–360.CrossRefGoogle Scholar
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, 171–179.CrossRefGoogle ScholarPubMed
Figure 0

Figure 1. Powder X-ray diffraction pattern of escitalopram oxalate oxalic acid hydrate, with the molecular structure.