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Powder X-ray diffraction of azelastine hydrochloride, C22H25ClN3O·Cl

Published online by Cambridge University Press:  18 November 2020

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 azelastine hydrochloride crystallizes in the monoclinic space group P21/n (#14) with a = 13.7844(5), b = 16.39920(14), c = 9.41231(22) Å, β = 97.5340(20)°, V = 2109.32(4) Å3, and Z = 4. The lattice parameters differ by −0.02, +0.04, and +0.04% from those in the previous determination (reflecting differences in the temperature and the sample source), and are more precise, from the use of synchrotron radiation. The experimental powder pattern is included in the Powder Diffraction File™ (PDF®) as entry 00-070-1219.

Keywords

azelastine hydrochlorideX-ray diffractionpowder diffraction file

Information

Type
Data Report
Information
Powder Diffraction , Volume 36 , Issue 1 , March 2021 , pp. 63 - 64
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Copyright
Copyright © The Author(s), 2020. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

Azelastine hydrochloride (Astelin® and additional trade names) is an antihistamine used to relieve nasal symptoms caused by allergies, administered as a dilute nasal solution. Commercial azelastine hydrochloride crystallizes in the monoclinic space group P21/n (#14) with a = 13.7844(5), b = 16.39920(14), c = 9.41231(22) Å, β = 97.5340(20)°, V = 2109.32(4) Å3, and Z = 4. A search of the powder data against the Powder Diffraction File™ (Gates-Rector and Blanton, Reference Gates-Rector and Blanton2019) and a reduced cell search in the Cambridge Structural Database (Groom et al., Reference Groom, Bruno, Lightfoot and Ward2016) yielded a previous structure determination (Maccaroni et al., Reference Maccaroni, Alberti, Malpezzi, Razzetti, Vladiskovic and Masciocchi2009; PDF® 02-099-8015 and CSD POVRUO). In this work, the sample was ordered from USP (Lot #F0L494) and analyzed as-received. The room temperature (295 K) crystal structure was refined using synchrotron (λ = 0.412849 Å) powder diffraction data. Hydrogen positions were included as part of the structure and were recalculated during the refinement. The diffraction data were collected on beamline 11-BM at the Advanced Photon Source, Argonne National Laboratory. Figure 1 shows the powder X-ray diffraction pattern of the compound. The lattice parameters differ by −0.02, +0.04, and +0.04% from those in the previous determination (reflecting differences in the temperature and the sample source), and are more-precise, from the use of synchrotron radiation. The two molecular structures are essentially identical, with a root-mean-square Cartesian displacement of 0.141 Å. The experimental powder pattern is included in the Powder Diffraction File™ (PDF®) as entry 00-070-1219.

Figure 1.

Powder X-ray diffraction pattern of azelastine hydrochloride, with the molecular structure.

All of the bond distances, angles, and torsion angles fall within the normal ranges indicated by a Mercury Mogul Geometry check (Macrae et al., Reference Macrae, Sovago, Cottrell, Galek, McCabe, Pidcock, Platings, Shields, Stevens, Towler and Wood2020). The crystal structure consists of layers of folded azelastine cations parallel to the ac-plane. The chloride anions reside between these layers. As expected, there is a strong discrete N5–H28⋯Cl53 between the cation and the anion (N–H = 0.958 Å, H⋯Cl = 2.081 Å, N⋯Cl = 2.993 Å, N–H⋯Cl = 158.3°). A number of relatively short C–H⋯Cl distances suggest the presence of additional significant intermolecular interactions.

ACKNOWLEDGMENTS

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 Crystallographic Information Framework (CIF) file containing the results of the Rietveld refinement (including the raw data) was deposited with the ICDD. The data can be requested at info@icdd.com.

References

Gates-Rector, S. D. and Blanton, T. N. (2019). “The Powder Diffraction File: a quality materials characterization database,” Powd. 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
Maccaroni, E., Alberti, E., Malpezzi, L., Razzetti, G., Vladiskovic, C., and Masciocchi, N. (2009). “Azelastine hydrochloride: a powder diffraction and 13C CPMAS NMR study of Its anhydrous and solvated forms,” Crystal. Growth Design 9(1), 517–524.CrossRefGoogle Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M., and Wood, P. A. (2020). “Mercury 4.0; from visualization to design and prediction,” J. Appl. Crystallogr. 53, 226–235.CrossRefGoogle ScholarPubMed
Figure 0

Figure 1. Powder X-ray diffraction pattern of azelastine hydrochloride, with the molecular structure.