Hostname: page-component-586b7cd67f-t8hqh Total loading time: 0 Render date: 2024-11-23T07:33:35.407Z Has data issue: false hasContentIssue false
  • English
  • Français

Crystal structure of hydrocortisone acetate, C23H32O6

Published online by Cambridge University Press:  11 January 2017

James A. Kaduk ,
Amy M. Gindhart  and
Thomas N. Blanton
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616 North Central College, 30 N. Brainard St., Naperville, Illinois 60540
Amy M. Gindhart
Affiliation:
International Centre for Diffraction Data, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
International Centre for Diffraction Data, 12 Campus Blvd., Newtown Square, Pennsylvania 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 hydrocortisone acetate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Hydrocortisone acetate crystallizes in space group P21 (#4) with a = 8.85173(3) Å, b = 13.53859(3) Å, c = 8.86980(4) Å, β = 101.5438(3)°, V = 1041.455(6) Å3, and Z = 2. Both hydroxyl groups form hydrogen bonds to the ketone oxygen atom on the steroid ring system, resulting in a three-dimensional hydrogen bond network. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File™.

Keywords

hydrocortisone acetatepowder diffractionRietveld refinementdensity functional theory
Type
Technical Articles
Information
Powder Diffraction , Volume 32 , Issue 1 , March 2017 , pp. 31 - 34
Check for updates
Copyright
Copyright © International Centre for Diffraction Data 2017 

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

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. Enl. 34(15), 1555–1573.Google Scholar
Biles, J. A. (1963). “Some crystalline modifications of the tert-Butylacetates of prednisolone and hydrocortisone,” J. Pharm. Sci. 52, 1066–1070.CrossRefGoogle ScholarPubMed
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. Comput. Sci. 44, 2133–2144.Google Scholar
Callow, R. K. and Kennard, O. (1961). “Polymorphism of cortisone acetate,” J. Pharm. Pharmacol. 13, 723–733.Google Scholar
Dassault Systèmes (2014). Materials Studio 8.0 (BIOVIA, San Diego, CA).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., 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.CrossRefGoogle 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. & 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.Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. B: Struct. Sci. Cryst. Eng. Mater. 72, 171–179.Google Scholar
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129–138.Google Scholar
ICDD (2015). PDF-4+ 2015 (Database). International Centre for Diffraction Data, edited by Dr. Soorya Kabekkodu (Newtown Square, PA, USA).Google Scholar
Kaduk, J. A., Crowder, C. E., Zhong, K., Fawcett, T. G., and Suchomel, M. R. (2014). “Crystal structure of atomoxetine hydrochloride (Strattera), C17H22NOCl,” Powder Diffr. 29(3), 269–273.Google Scholar
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System, (GSAS) (Report LAUR 86-784). 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.CrossRefGoogle ScholarPubMed
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Eddington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P. A. (2008). “Mercury CSD 2.0 B 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: Struct. Sci. Cryst. Eng. Mater. 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. Informatics 3, 33. doi: 10.1186/1758-2946-3-33.Google Scholar
Parsons, J., Wong, S. T., Beher, W. T., and Baker, G. D. (1962). “X-ray diffraction powder data for steroids: supplement II,” Henry Ford Hosp. Med. Bull. 10, 471–486.Google Scholar
Shell, J. W. (1955). “Hydrocortisone acetate,” Anal. Chem. 27, 1665–1666; CSD Refcode ZZZGCU.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: Struct. Sci. Cryst. Eng. Mater. 56(3), 455–465.Google Scholar
Shikii, K., Sakamoto, S., Seki, H., Utsumi, H., and Yamaguchi, K. (2004). “Narcissistic aggregation of steroid compounds in diluted solution elucidated by CSI-MS, PFG NMR and X-ray analysis,” Tetrahedron 60, 3487–3492; CSD Refcode CORTMS01.Google Scholar
Spackman, M. A. and Jayatilaka, D. (2009). ” A Hirshfeld surface analysis,” CrystEngComm 11, 19–32.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.CrossRefGoogle 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
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: Struct. Sci., Cryst. Eng. Mater. 70(6), 1020–1032.Google 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
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
Supplementary material: File

Kaduk supplementary material

Kaduk supplementary material 1

Download Kaduk supplementary material(File)
File 2.8 MB
Supplementary material: File

Kaduk supplementary material

Kaduk supplementary material 2

Download Kaduk supplementary material(File)
File 6.9 KB