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Crystal structure of salmeterol xinafoate form I (Serevent®Diskus®), (C25H37NO4)(C11H8O3)

Published online by Cambridge University Press:  11 November 2015

James A. Kaduk ,
Kai Zhong ,
Amy M. Gindhart  and
Thomas N. Blanton
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616
Kai Zhong
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of salmeterol xinafoate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Salmeterol xinafoate crystallizes in space group P−1 (#2) with a = 9.173 89(13), b = 9.483 79(14), c = 21.3666(4) Å, α = 82.2646(13), β = 85.2531(12), γ = 62.1565(11)°, V = 1628.37(5) Å3, and Z = 2. Key to the structure solution was linking the two fragments by a Li atom along the expected N–H···O hydrogen bond. The salmeterol cation and xinafoate anion are linked by N–H···O and O–H···O hydrogen bonds, interactions which cause the salmeterol to adjust its conformation. The hydrogen bonds result in complex chains along the b-axis. The powder pattern is included in the Powder Diffraction File™ as entry 00-065-1430.

Keywords

salmeterol xinafoateSerevent Diskuspowder diffractionRietveld refinementdensity functional theory
Type
Technical Articles
Information
Powder Diffraction , Volume 30 , Issue 4 , December 2015 , pp. 333 - 339
Copyright
Copyright © International Centre for Diffraction Data 2015 

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References

Accelrys (2013). Materials Studio 7.0 (Accelrys Software Inc., San Diego, CA).Google Scholar
Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Crystallogr., B: Struct. Sci. 58, 380–388.CrossRefGoogle ScholarPubMed
Altomare, A., Cuocci, C., Giacovazzo, C., Moliterni, A., Rizzi, R., Corriero, N., and Falcicchio, A. (2013). “EXPO2013: a kit of tools for phasing crystal structures from powder data”, J. Appl. Crystallogr. 46, 1231–1235.Google Scholar
Beach, S., Latham, D., Sidgwick, C., Hanna, M., and York, P. (1999). “Control of the physical form of salmeterol xinafoate,” Org. Proc. Res. Dev. 3, 370–376.Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L., and Chang, N. L. (1995). “Patterns in hydrogen bonding: functionality and graph set analysis in crystals,” Angew. Chem. Int. Ed. Engl. 34(15), 1555–1573.Google Scholar
Bravais, A. (1866). Etudes Cristallographiques (Gauthier Villars, Paris).Google Scholar
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E., and Orpen, A. G. (2004). “Retrieval of crystallographically-derived molecular geometry information,” J. Chem. Inf. Sci. 44, 2133–2144.Google Scholar
David, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S., and Cole, J. C. (2006). “DASH: a program for crystal structure determination from powder diffraction data,” J. Appl. Crystallogr. 39, 910–915.Google Scholar
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am.. Mineral. 22, 446–467.Google Scholar
Dovesi, R., Saunders, V. R., Roetti, C., Orlando, R., Zicovich-Wilson, C. M., Pascale, F., Civalleri, B., Doll, K., Harrison, N. M., Bush, I. J., D-Arco, Ph., Llunell, M., Causà, M., and Noël, Y. (2014). CRYSTAL14 User's Manual. University of Torino; http://www.crystal.unito.it.Google Scholar
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120–126.Google Scholar
Favre-Nicolin, V. and Černý, R. (2002). “FOX, Free Objects for crystallography: a modular approach to ab initio structure determination from powder diffraction,” J. Appl. Crystallogr. 35, 734–743.Google Scholar
Finger, L. W., Cox, D. E., and Jephcoat, A. P. (1994). “A correction for powder diffraction peak asymmetry due to axial divergence,” J. Appl. Crystallogr. 27(6), 892–900.Google Scholar
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral. 30, 326–455.Google Scholar
Gatti, C., Saunders, V. R., and Roetti, C. (1994). “Crystal-field effects on the topological properties of the electron-density in molecular crystals – the case of urea,” J. Chem. Phys. 101, 10686–10696.CrossRefGoogle Scholar
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129–138.Google Scholar
ICDD (2014), PDF-4+ 2014 (Database), edited by Dr. Soorya Kabekkodu International Centre for Diffraction Data, Newtown Square, PA, USA.Google Scholar
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System (GSAS), (Report LAUR 86-784). Los Alamos, New Mexico: Los Alamos National Laboratory.Google Scholar
Lee, P. L., Shu, D., Ramanathan, M., Preissner, C., Wang, J., Beno, M. A., Von Dreele, R. B., Ribaud, L., Kurtz, C., Antao, S. M., Jiao, X., and Toby, B. H. (2008). “A twelve-analyzer detector system for high-resolution powder diffraction,” J. Synchrotron Radiat. 15(5), 427–432.Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P. A. (2008). “Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures,” J. Appl. Crystallogr. 41, 466–470.Google Scholar
McKinnon, J. J., Spackman, M. A., and Mitchell, A. S. (2004). “Novel tools for visualizing and exploring intermolecular interactions in molecular crystals,” Acta Crystallogr. B 60, 627–668.Google Scholar
MDI (2014). Jade 9.5 (Materials Data. Inc., Livermore, CA).Google Scholar
O'Boyle, N., Banck, M., James, C. A., Morley, C., Vandermeersch, T., and Hutchison, G. R. (2011). “Open Babel: an open chemical toolbox,” J. Chem. Inf. 3, 33. DOI: 10.1186/1758-2946-3-33.Google Scholar
Shields, G. P., Raithby, P. R., Allen, F. H., and Motherwell, W. S. (2000). “The assignment and validation of metal oxidation states in the Cambridge Structural Database,” Acta Crystallogr. B 56(3), 455–465.CrossRefGoogle ScholarPubMed
Spackman, M. A. and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” Cryst. Eng. Commun. 11, 19–32.CrossRefGoogle Scholar
Stephens, P. W. (1999). “Phenomenological model of anisotropic peak broadening in powder diffraction,” J. Appl. Crystallogr. 32, 281–289.Google Scholar
Sykes, R. A., McCabe, P., Allen, F. H., Battle, G. M., Bruno, I. J., and Wood, P. A. (2011). “New software for statistical analysis of Cambridge Structural Database data,” J. Appl. Crystallogr. 44, 882–886.Google Scholar
Thompson, P., Cox, D. E., and Hastings, J. B. (1987). “Rietveld refinement of Debye-Scherrer synchrotron X-ray data from Al2O3 ,” J. Appl. Crystallogr. 20(2), 79–83.Google Scholar
Toby, B. H. (2001). “EXPGUI, a graphical user interface for GSAS,” J. Appl. Crystallogr. 34, 210–213.Google Scholar
Tong, H. H. Y., Shekunov, B. Yu., York, P., and Chow, A. H. L. (2001). “Characterization of two polymorphs of salmeterol xinafoate crystallized from supercritical fluids,” Pharm. Res. 18, 852–858.Google Scholar
van de Streek, J. and Neumann, M. A. (2014). “Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D),” Acta Crystallogr. B 70(6), 1020–1032.CrossRefGoogle ScholarPubMed
Wang, J., Toby, B. H., Lee, P. L., Ribaud, L., Antao, S. M., Kurtz, C., Ramanathan, M., Von Dreele, R. B., and Beno, M. A. (2008). “A dedicated powder diffraction beamline at the Advanced Photon Source: commissioning and early operational results,” Rev. Sci. Instrum. 79, 085105.Google Scholar
Wavefunction, Inc. (2013). Spartan ‘14 Version 1.1.0 (Wavefunction Inc.), 18401 Von Karman Ave., Suite 370, Irvine CA 92612.Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, M. J., Turner, M. J., Jayatilaka, D., and Spackman, M. A. (2012). CrystalExplorer Version 3.1 (University of Western Australia).Google Scholar
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