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Volume 68 
Part 1 
Page o237  
January 2012  

Received 7 December 2011
Accepted 16 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.138
Data-to-parameter ratio = 21.7
Details
Open access

5[alpha],6[alpha]-Epoxy-7-norcholestan-3[beta]-yl acetate

aCEMDRX, Department of Physics, Faculty of Sciences and Technology, University of Coimbra, P-3004-516 Coimbra, Portugal,bCentre for Neuroscience and Cell Biology, University of Coimbra, P-3004-517 Coimbra, Portugal, and cFaculty of Pharmacy, University of Coimbra, P-3000-548 Coimbra, Portugal
Correspondence e-mail: jap@pollux.fis.uc.pt

The title cholestan, C28H46O3, was prepared by epoxidation of 7-norcholest-5-en-3[beta]-yl acetate and crystallized by slow evaporation from an ethanolic solution. All rings are trans fused. The 3[beta]-acetate and the 17[beta]-cholestane side chain are in equatorial positions. The molecule is highly twisted due to its B-nor characteristic. A quantum chemical ab-initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated molecule gives values for bond lengths and valency angles in close agreement with the experimental ones.

Related literature

For the chemistry of the title compound, see: Carvalho et al. (2009a[Carvalho, J. F. S., Silva, M. M. C., Moreira, J. N., Simões, S. & Sá e Melo, M. L. (2009a). J. Med. Chem. 52, 4007-4019.], 2010a[Carvalho, J. F. S., Silva, M. M. C., Moreira, J. N., Simões, S. & Sá e Melo, M. L. (2010a). J. Med. Chem. 53, 7632-7638.]). For studies of biological activity of steroids, see: Carvalho et al. (2009b[Carvalho, J. F. S., Silva, M. M. C. & Sá e Melo, M. L. (2009b). Tetrahedron, 65, 2773-2781.], 2010b[Carvalho, J. F. S., Silva, M. M. C. & Sá e Melo, M. L. (2010b). Tetrahedron, 66, 2455-2462.]). For the influence of structural characteristics of B-nor steroids on the outcome of many reactions, see: Uyanik & Hanson (2009)[Uyanik, C. & Hanson, J. R. (2009). J. Chem. Res. 12, 713-719.]. For asymmetry parameters, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structure. New York: Plenum Press.]); Altona et al. (1968[Altona, C., Geise, H. J. & Romers, C. (1968). Tetrahedron, 24, 13-32.]). For reference bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the melting point of the title compound, see: Joska et al. (1963[Joska, J., Fajkos, J. & Sorm, F. (1963). Collect. Czech. Chem. Commun. 28, 82-99.]). For the software used in ab-initio calculations, see Schmidt et al. (1993[Schmidt, M. W., Baldrige, K. K., Boatz, J. A., Elbert, S. T., Gordon, M. S., Jensen, J. J., Koseki, S., Matsunaga, N., Nguyen, K. A., Sue, S., Windus, T. L., Dupuis, M. & Montgomery, J. A. (1993). J. Comput. Chem. 14, 1347-1363.]).

[Scheme 1]

Experimental

Crystal data
  • C28H46O3

  • Mr = 430.65

  • Monoclinic, P 21

  • a = 7.5820 (1) Å

  • b = 9.7487 (1) Å

  • c = 17.8588 (2) Å

  • [beta] = 93.1792 (18)°

  • V = 1318.00 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.44 × 0.24 × 0.16 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.989

  • 35109 measured reflections

  • 6194 independent reflections

  • 3551 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.138

  • S = 0.96

  • 6194 reflections

  • 286 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2846 Friedel pairs

  • Flack parameter: -0.5 (15)

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2347 ).


Acknowledgements

This work was supported by funds from FEDER via the COMPETE (Programa Operacional Factores de Competitividade) programme and by the FCT (Fundação para a Ciência e a Tecnologia) (project PEst-C/FIS/UI0036/2011). We gratefully acknowledge the LCA-UC for a grant of computer time in the Milipeia cluster.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altona, C., Geise, H. J. & Romers, C. (1968). Tetrahedron, 24, 13-32.  [CrossRef] [ChemPort] [ISI]
Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Carvalho, J. F. S., Silva, M. M. C., Moreira, J. N., Simões, S. & Sá e Melo, M. L. (2009a). J. Med. Chem. 52, 4007-4019.  [PubMed] [ChemPort]
Carvalho, J. F. S., Silva, M. M. C., Moreira, J. N., Simões, S. & Sá e Melo, M. L. (2010a). J. Med. Chem. 53, 7632-7638.  [ChemPort] [PubMed]
Carvalho, J. F. S., Silva, M. M. C. & Sá e Melo, M. L. (2009b). Tetrahedron, 65, 2773-2781.  [ChemPort]
Carvalho, J. F. S., Silva, M. M. C. & Sá e Melo, M. L. (2010b). Tetrahedron, 66, 2455-2462.  [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structure. New York: Plenum Press.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Joska, J., Fajkos, J. & Sorm, F. (1963). Collect. Czech. Chem. Commun. 28, 82-99.  [ChemPort]
Schmidt, M. W., Baldrige, K. K., Boatz, J. A., Elbert, S. T., Gordon, M. S., Jensen, J. J., Koseki, S., Matsunaga, N., Nguyen, K. A., Sue, S., Windus, T. L., Dupuis, M. & Montgomery, J. A. (1993). J. Comput. Chem. 14, 1347-1363.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Uyanik, C. & Hanson, J. R. (2009). J. Chem. Res. 12, 713-719.


Acta Cryst (2012). E68, o237  [ doi:10.1107/S1600536811054249 ]

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