Hostname: page-component-586b7cd67f-t7fkt Total loading time: 0 Render date: 2024-11-26T17:24:09.476Z Has data issue: false hasContentIssue false
  • English
  • Français

Crystal structure of fingolimod hydrochloride, C19H34ClNO2

Published online by Cambridge University Press:  12 August 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, Pennsylnia 19073-3273
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylnia 19073-3273
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
Get access Rights & Permissions [Opens in a new window]

Abstract

The crystal structure of fingolimod hydrochloride (C19H34ClNO2) has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Fingolimod hydrochloride crystallizes in space group P21/n (#14) with a = 7.137 53(5), b = 5.957 98(4), c = 49.5196(4) Å, β = 91.0808(7)°, V = 2105.46(2) Å3, and Z = 4. The structure consists of a “lipid bilayer” packing. The polar ends of the molecules make O–H···Cl and N–H···Cl hydrogen bonds to the chloride anion, and the octyl side chains pack adjacent to each other. The hydrogen bonds form three types of chains with graph sets C1,2(7), C1,2(7), and C1,2(8). The result is a complex chain of hydrogen bonds parallel to the b-axis. The powder pattern has been submitted to ICDD for inclusion in future releases of the Powder Diffraction File™.

Keywords

fingolimodGilenyapowder diffractionRietveld refinementdensity functional theory
Type
Technical Articles
Information
Powder Diffraction , Volume 30 , Issue 3 , September 2015 , pp. 205 - 210
Check for updates
Copyright
Copyright © International Centre for Diffraction Data 2015 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

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. Sect. B: Struct. Sci. 58, 380–388.Google Scholar
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
Apra, E., Causa, M., Prencipe, M., Dovesi, R., and Saunders, V. R. (1993). “On the structural properties of NaCl: an ab initio study of the B1–B2 phase transition,” J. Phys., Condens. Matter 5(18), 2969–2976.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
Billich, A., Bornancin, F., Dévay, P., Mechtcheriakova, D., Urtz, N., and Baumruker, T. (2003). “Phosphorylation of the immunomodulatory drug FTY720 by sphingosine kinases,” J. Biol. Chem. 278(48), 47408–47415.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
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Amer. Mineral. 22, 446–467.Google Scholar
Dovesi, R., Orlando, R., Civalleri, B., Roetti, C., Saunders, V. R., and Zicovich-Wilson, C. M. (2005). “CRYSTAL: a computational tool for the ab initio study of the electronic properties of crystals,” Z. Kristallogr. 220, 571–573.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
ICDD (2014). PDF-4+ 2014 (Database), edited by Dr. Soorya Kabekkodu, Int. Centre for Diffraction Data, Newtown Square, PA, USA.Google Scholar
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System, (GSAS) (Los Alamos National Laboratory Report LAUR 86-784).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. Synchroton Radiat. 15(5), 427–432.Google Scholar
Louër, D. and Boultif, A. (2007). “Powder pattern indexing and the dichotomy algorithm,” Z. Kristallogr. S26, 191–196.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.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. Sec. B: Struct. Sci. 56(3), 455–465.Google Scholar
Shrawat, V. K., Veereshappa, N., Singh, V. K., and Purohit, P. (2013). “Fingolimod polymorphs and their processes,” US Patent 2013/0281739 A1.Google 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.CrossRefGoogle Scholar
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
Supplementary material: File

Kaduk supplementary material

Kaduk supplementary material 1

Download Kaduk supplementary material(File)
File 2.7 MB
Supplementary material: File

Kaduk supplementary material

Kaduk supplementary material 2

Download Kaduk supplementary material(File)
File 8.9 KB