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Volume 69 
Part 5 
Pages o795-o796  
May 2013  

Received 28 March 2013
Accepted 23 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.141
Data-to-parameter ratio = 8.3
Details
Open access

Lup-20(29)-en-28-ol-3-one (betulone)

aDepartment of Organic Chemistry, Medical University of Silesia, Sosnowiec 41-200, Poland,bDepartment of Organic Chemistry, Wroclaw Medical University, Wroclaw 50-556, Poland,cDepartment of Physics of Crystals, Institute of Physics, University of Silesia, Katowice 40-007, Poland, and dDepartment of Solid State Physics, Institute of Physics, University of Silesia, Katowice 40-007, Poland
Correspondence e-mail: boryczka@sum.edu.pl

The asymmetric unit of the title compound, C30H48O2, contains two independent molecules, the main difference between them being that the isopropenyl group is rotated by approximately 180°. In each molecule, the fused six-membered rings have chair-chair-chair-chair conformations and the cyclopentane ring adopts an envelope conformation with the C atom bearing the hydroxymethyl group as the flap. All ring junctions are trans-fused. With the exception of one of the methyl groups adjacent to the C=O group, all the methyl groups are in axial positions. The isopropenyl group is equatorial and the hydroxymethyl group is in an axial orientation. In the crystal, weak C-H...O interactions link the molecules into chains along [010]. Weak intramolecular C-H...O hydrogen bonds are also observed but the hydroxy groups are not involved in hydrogen bonds.

Related literature

For the synthesis of betulone, see: Hase et al. (1981[Hase, T. A., Suokas, E. & Weckman, A. (1981). Synth. Commun. 11, 489-492.]). For the isolation of betulone from plants, see: Cole et al. (1991[Cole, B. J. W., Bentley, M. D. & Hua, Y. (1991). Hölzforschung, 45, 265-268.]); Reyes et al. (2006[Reyes, C. P., Núnez, M. J., Jiménez, I. A., Busserolles, J., Alcaraz, M. J. & Bazzocchi, I. L. (2006). Bioorg. Med. Chem. 14, 1573-1579.]); Diouf et al. (2009[Diouf, P. N., Stevanovic, T. & Boutin, Y. (2009). Ind. Crops Prod. 30, 297-303.]); Liu et al. (2010[Liu, Z., Jiang, W., Deng, Z.-W. & Lin, W.-H. (2010). J. Chin. Pharm. Sci. 19, 387-392.]); Kim et al. (2002[Kim, D. K., Nam, I. Y., Kim, J. W., Shin, T. Y. & Lim, J. P. (2002). Arch. Pharm. Res. 25, 617-620.]); Garcez et al. (2003[Garcez, F. R., Garcez, W. S., Miguel, D. L. S., Serea, A. A. T. & Prado, F. C. (2003). J. Braz. Chem. Soc. 14, 461-465.]); Fuchino et al. (1996[Fuchino, H., Konishi, S., Satoh, T., Yagi, A., Saitsu, K., Tatsumi, T. & Tanaka, N. (1996). Chem. Pharm. Bull. 44, 1033-1038.]). For the biological activity of betulone, see: Alakurtti et al. (2010[Alakurtti, S., Bergstrom, P., Sacerdoti-Sierra, N., Jaffe, C. L. & Yli-Kauhaluoma, J. (2010). J. Antibiot. 63, 123-126.]); Hata et al. (2002[Hata, K., Hori, K. & Takahashi, S. (2002). J. Nat. Prod. 65, 645-648.]); Reyes et al. (2006[Reyes, C. P., Núnez, M. J., Jiménez, I. A., Busserolles, J., Alcaraz, M. J. & Bazzocchi, I. L. (2006). Bioorg. Med. Chem. 14, 1573-1579.]). For related structures, see: Mohamed et al. (2006[Mohamed, I. E., Choudhary, M. I., Ali, S., Anjum, S. & Atta-ur-Rahman, (2006). Acta Cryst. E62, o1352-o1354.]); Ding et al. (2009[Ding, W.-M., Jing, L.-J., Yu, T., Wang, Y. & Yan, X.-F. (2009). Acta Cryst. E65, o1982.]); Drebushchak et al. (2010[Drebushchak, T. N., Mikhailenko, M. A., Brezgunova, M. E., Shakhtshneider, T. P. & Kuznetsova, S. A. (2010). J. Struct. Chem. 51, 798-801.]); Boryczka et al. (2011[Boryczka, S., Michalik, E., Jastrzebska, M., Kusz, J., Zubko, M. & Bebenek, E. (2011). J. Chem. Crystallogr. 42, 345-351.], 2012a[Boryczka, S., Bebenek, E., Jastrzebska, M., Kusz, J. & Zubko, M. (2012a). Z. Kristallogr. 227, 379-384.],b[Boryczka, S., Jastrzebska, M., Bebenek, E., Kusz, J., Zubko, M., Kadela, M. & Michalik, E. (2012b). J. Pharm. Sci. 101, 4458-4471.]).

[Scheme 1]

Experimental

Crystal data
  • C30H48O2

  • Mr = 440.71

  • Orthorhombic, P 21 21 21

  • a = 9.4447 (3) Å

  • b = 19.1818 (6) Å

  • c = 28.1141 (7) Å

  • V = 5093.3 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.60 × 0.56 × 0.20 mm

Data collection
  • Oxford Diffraction diffractometer with a Sapphire3 detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]) Tmin = 0.960, Tmax = 0.986

  • 61473 measured reflections

  • 5036 independent reflections

  • 4401 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.141

  • S = 1.03

  • 5036 reflections

  • 609 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13A-H13A...O2A 1.04 (4) 2.52 (3) 3.186 (4) 122 (2)
C13B-H13B...O2B 1.02 (3) 2.47 (3) 3.165 (4) 125 (2)
C19A-H19A...O2A 0.95 (4) 2.45 (4) 3.006 (5) 118 (3)
C22B-H22C...O1Bi 1.05 (4) 2.56 (4) 3.567 (4) 160 (3)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.]); data reduction: CrysAlis RED; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5603 ).


Acknowledgements

This work was supported by the Medical University of Silesia in Katowice, Poland (grant No. KNW-1-006/P/2/0).

References

Alakurtti, S., Bergstrom, P., Sacerdoti-Sierra, N., Jaffe, C. L. & Yli-Kauhaluoma, J. (2010). J. Antibiot. 63, 123-126.  [CrossRef] [ChemPort] [PubMed]
Boryczka, S., Bebenek, E., Jastrzebska, M., Kusz, J. & Zubko, M. (2012a). Z. Kristallogr. 227, 379-384.  [CSD] [CrossRef] [ChemPort]
Boryczka, S., Jastrzebska, M., Bebenek, E., Kusz, J., Zubko, M., Kadela, M. & Michalik, E. (2012b). J. Pharm. Sci. 101, 4458-4471.  [CSD] [CrossRef] [ChemPort] [PubMed]
Boryczka, S., Michalik, E., Jastrzebska, M., Kusz, J., Zubko, M. & Bebenek, E. (2011). J. Chem. Crystallogr. 42, 345-351.  [CSD] [CrossRef]
Cole, B. J. W., Bentley, M. D. & Hua, Y. (1991). Hölzforschung, 45, 265-268.  [CrossRef] [ChemPort]
Ding, W.-M., Jing, L.-J., Yu, T., Wang, Y. & Yan, X.-F. (2009). Acta Cryst. E65, o1982.  [CSD] [CrossRef] [details]
Diouf, P. N., Stevanovic, T. & Boutin, Y. (2009). Ind. Crops Prod. 30, 297-303.  [CrossRef] [ChemPort]
Drebushchak, T. N., Mikhailenko, M. A., Brezgunova, M. E., Shakhtshneider, T. P. & Kuznetsova, S. A. (2010). J. Struct. Chem. 51, 798-801.  [CrossRef] [ChemPort]
Fuchino, H., Konishi, S., Satoh, T., Yagi, A., Saitsu, K., Tatsumi, T. & Tanaka, N. (1996). Chem. Pharm. Bull. 44, 1033-1038.  [CrossRef] [ChemPort]
Garcez, F. R., Garcez, W. S., Miguel, D. L. S., Serea, A. A. T. & Prado, F. C. (2003). J. Braz. Chem. Soc. 14, 461-465.  [CrossRef] [ChemPort]
Hase, T. A., Suokas, E. & Weckman, A. (1981). Synth. Commun. 11, 489-492.  [CrossRef] [ChemPort]
Hata, K., Hori, K. & Takahashi, S. (2002). J. Nat. Prod. 65, 645-648.  [CrossRef] [PubMed] [ChemPort]
Kim, D. K., Nam, I. Y., Kim, J. W., Shin, T. Y. & Lim, J. P. (2002). Arch. Pharm. Res. 25, 617-620.  [CrossRef] [PubMed] [ChemPort]
Liu, Z., Jiang, W., Deng, Z.-W. & Lin, W.-H. (2010). J. Chin. Pharm. Sci. 19, 387-392.  [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mohamed, I. E., Choudhary, M. I., Ali, S., Anjum, S. & Atta-ur-Rahman, (2006). Acta Cryst. E62, o1352-o1354.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abington, England.
Reyes, C. P., Núnez, M. J., Jiménez, I. A., Busserolles, J., Alcaraz, M. J. & Bazzocchi, I. L. (2006). Bioorg. Med. Chem. 14, 1573-1579.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o795-o796   [ doi:10.1107/S1600536813011008 ]

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