Skip to main content Accessibility help
×
Home

Crystal structure of prednicarbate, C27H36O8

  • Zachary R. Butler (a1), James A. Kaduk (a1) (a2), Amy M. Gindhart (a3) and Thomas N. Blanton (a3)

Abstract

The crystal structure of prednicarbate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Prednicarbate crystallizes in space group P212121 (#19) with a = 7.69990(3), b = 10.75725(3), c = 31.36008(11) Å, V = 2597.55(1) Å3, and Z = 4. In the crystal structure the long axis of the steroid ring system lies roughly parallel to the c-axis. The oxygenated side chains are orientated roughly perpendicular to the steroid ring system and are adjacent to each other, parallel to the ab-plane. The only traditional hydrogen bond donor in the prednicarbate molecule is the hydroxyl group O32–H33, but this does not participate in an O–H···O hydrogen bond. The nearest oxygen atoms to O32 are symmetry-related O32 at 4.495 Å, precluding the expected O–H···O hydrogen bond. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™.

Copyright

Corresponding author

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

References

Hide All
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.
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.
Dassault Systèmes (2018). Materials Studio 2019R1 (BIOVIA, San Diego, CA).
Donnay, J. D. H., and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am. Mineral. 22, 446447.
Dovesi, R., Orlando, R., Erba, A., Zicovich-Wilson, C. M., Civalleri, B., Casassa, S., Maschio, L., Ferrabone, M., De La Pierre, M., D-Arco, P., Noël, Y., Causà, M., and Kirtman, B. (2014). “CRYSTAL14: a program for the ab initio investigation of crystalline solids,” Int. J. Quantum Chem. 114, 12871317.
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.
Fawcett, T. G., Kabekkodu, S. N., Blanton, J. R., and Blanton, T. N. (2017). “Chemical analysis by diffraction: the Powder Diffraction file™,” Powder Diffr. 32(2), 6371.
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.
Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. B. 72, 171179.
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta. 44, 129138.
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), 269273.
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. Synch. 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.
MDI (2018). Jade 9.8 (Materials Data Inc., Livermore, CA).
Neto, H. S., de Araujo, G. L. B., dos Santos, L. L., Cosentino, I. C., Carvalho, F. M., and Matos, J. R. (2015). “Inclusion of prednicarbate in the SBA-15 silica,” J. Therm. Anal. Calorim. 123, 22972305.
O'Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., and Hutchison, G. R. (2011). “Open Babel: an open chemical toolbox,” J. Chem. Inform. 3, 33.
Silk Scientific (2013). UN-SCAN-IT 7.0 (Silk Scientific Corporation, Orem, UT).
Sohn, Y.-T., and Kim, S.-Y. (2002). “Effect of crystal form on in vivo topical anti-inflammatory activity of corticosteriods,” Arch. Pharm. Res. 25, 556559.
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.
Toby, B. H., and Von Dreele, R. B. (2013). “GSAS II: the genesis of a modern open source all purpose crystallography software package,” J. Appl. Crystallogr. 46, 544549.
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D., and Spackman, M. A. (2017). CrystalExplorer17 (University of Western Australia). http://hirshfeldsurface.net.
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. 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. (2018). Spartan ‘18 Version 1.2.0 (Wavefunction Inc., Irvine, CA).

Keywords

Type Description Title
UNKNOWN
Supplementary materials

Butler et al. supplementary material
Butler et al. supplementary material 1

 Unknown (2.7 MB)
2.7 MB
UNKNOWN
Supplementary materials

Butler et al. supplementary material
Butler et al. supplementary material 2

 Unknown (8 KB)
8 KB

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