Skip to main content Accessibility help
×
Home

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

  • James A. Kaduk (a1), Kai Zhong (a2), Amy M. Gindhart (a2) and Thomas N. Blanton (a2)

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.

Copyright

Corresponding author

a) Author to whom correspondence should be addressed. Electronic mail: kaduk@polycrystallography.com

References

Hide All
Accelrys (2013). Materials Studio 7.0 (Accelrys Software Inc., San Diego, CA).
Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Crystallogr., B: Struct. Sci. 58, 380388.
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, 12311235.
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, 370376.
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), 15551573.
Bravais, A. (1866). Etudes Cristallographiques (Gauthier Villars, Paris).
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, 21332144.
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, 910915.
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am.. Mineral. 22, 446467.
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.
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120126.
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, 734743.
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), 892900.
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral. 30, 326455.
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, 1068610696.
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129138.
ICDD (2014), PDF-4+ 2014 (Database), edited by Dr. Soorya Kabekkodu International Centre for Diffraction Data, Newtown Square, PA, USA.
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.
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), 427432.
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, 466470.
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, 627668.
MDI (2014). Jade 9.5 (Materials Data. Inc., Livermore, CA).
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.
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), 455465.
Spackman, M. A. and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” Cryst. Eng. Commun. 11, 1932.
Stephens, P. W. (1999). “Phenomenological model of anisotropic peak broadening in powder diffraction,” J. Appl. Crystallogr. 32, 281289.
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, 882886.
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), 7983.
Toby, B. H. (2001). “EXPGUI, a graphical user interface for GSAS,” J. Appl. Crystallogr. 34, 210213.
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, 852858.
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), 10201032.
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.
Wavefunction, Inc. (2013). Spartan ‘14 Version 1.1.0 (Wavefunction Inc.), 18401 Von Karman Ave., Suite 370, Irvine CA 92612.
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).

Keywords

Type Description Title
UNKNOWN
Supplementary materials

Kaduk supplementary material
Kaduk supplementary material 1

 Unknown (11 KB)
11 KB
UNKNOWN
Supplementary materials

Kaduk supplementary material
Kaduk supplementary material 2

 Unknown (2.7 MB)
2.7 MB

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

  • James A. Kaduk (a1), Kai Zhong (a2), Amy M. Gindhart (a2) and Thomas N. Blanton (a2)

Metrics

Full text views

Total number of HTML views: 0
Total number of PDF views: 0 *
Loading metrics...

Abstract views

Total abstract views: 0 *
Loading metrics...

* Views captured on Cambridge Core between <date>. This data will be updated every 24 hours.

Usage data cannot currently be displayed