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Volume 69 
Part 4 
Pages o467-o468  
April 2013  

Received 18 January 2013
Accepted 26 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.089
Data-to-parameter ratio = 10.0
Details
Open access

The furanosteroid viridiol

aDepartment of Chemistry, Uppsala BioCenter, P.O. Box 7015, Swedish University of Agricultural Sciences, SE-750 07 Uppsala, Sweden
Correspondence e-mail: daniel.lundberg@slu.se

The asymmetric unit of the title compound, C20H18O6 (systematic name: 1[beta],3[beta]-dihydroxy-2[beta]-methoxyfuro[4',3',2':4,5,6]-18-norandrosta-8,11,13-triene-7,17-dione), a dihydro derivative of the fungal steroid viridin, contains two molecules with similar conformations. The rings bearing the hydroxy groups adopt boat conformations. The absolute structure was assigned based on the known chirality of a precursor compound. In the crystal, molecules are linked by O-H...O hydrogen bonds, generating a three-dimensional network and weak C-H...O interactions consolidate the packing.

Related literature

For background to fungal metabolites, see: Brian & McGowan (1945[Brian, P. W. & McGowan, J. C. (1945). Nature, 156, 144-145.]); Moffatt et al. (1969[Moffatt, J. S., Bu'Lock, J. D. & Yuen, T. H. (1969). J. Chem. Soc. D, p. 839a.]); Jones & Hancock (1987[Jones, R. W. & Hancock, J. G. (1987). Can. J. Microbiol. 33, 963-966.]); Hanson (1995[Hanson, J. R. (1995). Nat. Prod. Rep. 12, 381-384.]); Cross et al. (1995[Cross, M. J., Stewart, A., Hodgkin, M. N., Kerr, D. J. & Wakelam, M. J. O. (1995). J. Biol. Chem. 270, 25352-25355.]); Przybyl (2002[Przybyl, K. (2002). For. Pathol. 32, 387-394.]); Smith et al. (2009[Smith, A., Blois, J., Yuan, H., Aikawa, E., Ellson, C., Figueiredo, J. L., Weissleder, R., Kohler, R., Yaffe, M. B., Cantley, L. C. & Josephson, L. (2009). Mol. Cancer Ther. 8, 1666-1675.]); Andersson et al. (2010[Andersson, P. F., Johansson, S. B. K., Stenlid, J. & Broberg, A. (2010). For. Pathol. 40, 43-46.]); Queloz et al. (2011[Queloz, V., Grunig, C. R., Berndt, R., Kowalski, T., Sieber, T. N. & Holdenrieder, O. (2011). For. Pathol. 41, 133-142.]); Andersson (2012[Andersson, P. F. (2012). PhD thesis, Swedish University of Agricultural Sciences, Uppsala, Sweden. Available at http://pub.epsilon.slu.se/8996 .]); Andersson et al. (2012[Andersson, P. F., Bengtsson, S., Stenlid, J. & Broberg, A. (2012). Molecules, 17, 7769-7781.], 2013[Andersson, P. F., Bengtsson, S., Cleary, M. R., Stenlid, J. & Broberg, A. (2013). Phytochemistry, 86, 195-200.]). For related structures, see: Neidle et al. (1972[Neidle, S., Rogers, D. & Hursthouse, M. B. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 760-766.]); Lang et al. (2009[Lang, Y., Souza, F. E. S., Xu, X., Taylor, N. J., Assoud, A. & Rodrigo, R. (2009). J. Org. Chem. 74, 5429-5439.]). For other characterization methods, see: Brian et al. (1957[Brian, P. W., Curtis, P. J., Hemming, H. G. & Norris, G. L. F. (1957). Trans. Br. Mycol. Soc. 40, 365-368.]); Aldridge et al. (1975[Aldridge, D. C., Turner, W. B., Geddes, A. J. & Sheldrick, B. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 943-945.]); Blight & Grove (1986[Blight, M. M. & Grove, J. F. (1986). J. Chem. Soc. Perkin Trans. 1, pp. 1317-1322.]). For background to the assignment of the absolute structure of the title compound, see: MacMillan et al. (1972[MacMillan, J., Simpson, T. J., Vanstone, A. E. & Yeboah, S. K. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 2892-2898.]); Harrison (1990[Harrison, D. M. (1990). Nat. Prod. Rep. 7, 459-484.]); Dewick (2002[Dewick, P. M. (2002). Nat. Prod. Rep. 19, 181-222.]); Wipf & Kerekes (2003[Wipf, P. & Kerekes, A. D. (2003). J. Nat. Prod. 66, 716-718.]); Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18O6

  • Mr = 354.34

  • Orthorhombic, P 21 21 21

  • a = 6.8285 (2) Å

  • b = 20.1939 (6) Å

  • c = 22.4344 (6) Å

  • V = 3093.57 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 93 K

  • 0.3 × 0.25 × 0.2 mm

Data collection
  • Oxford Diffraction XcaliburIII Sapphire-3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.891, Tmax = 1.000

  • 26916 measured reflections

  • 4874 independent reflections

  • 3294 reflections with I > 2[sigma](I)

  • Rint = 0.085

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.089

  • S = 0.91

  • 4874 reflections

  • 485 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O19A-H19A...O19Bi 0.85 (3) 2.08 (3) 2.886 (3) 160 (3)
O19B-H19B...O20Aii 0.83 (3) 2.30 (3) 3.002 (3) 143 (3)
O20A-H20A...O25Biii 0.91 (3) 1.85 (3) 2.717 (3) 160 (3)
O20B-H20B...O24Aiv 0.81 (3) 2.05 (3) 2.842 (3) 166 (3)
C2A-H2A...O23Bv 1.00 2.45 3.325 (3) 146
C2B-H2B...O23A 1.00 2.38 3.295 (3) 151
C11A-H11A...O19A 0.95 2.43 3.084 (3) 126
C11B-H11B...O19B 0.95 2.58 3.230 (3) 126
C18A-H18A...O20A 0.98 2.38 3.227 (3) 145
C18B-H18D...O20B 0.98 2.39 3.241 (4) 145
C21A-H21A...O24Avi 0.95 2.37 3.282 (3) 162
C21B-H21B...O24Bvii 0.95 2.25 3.180 (3) 167
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (v) x+1, y, z; (vi) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXD (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: SHELXL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: DIAMOND (Brandenburg, 2001[Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7028 ).


Acknowledgements

We are grateful to Dr Lars Eriksson for skillful technical assistance and fruitful discussions. The isolate Ö3 from which the viridiol was obtained was from a study which was, in part, supported by the Swedish research council FORMAS grant No. 2010-1344.

References

Aldridge, D. C., Turner, W. B., Geddes, A. J. & Sheldrick, B. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 943-945.  [CrossRef]
Andersson, P. F. (2012). PhD thesis, Swedish University of Agricultural Sciences, Uppsala, Sweden. Available at http://pub.epsilon.slu.se/8996 .
Andersson, P. F., Bengtsson, S., Cleary, M. R., Stenlid, J. & Broberg, A. (2013). Phytochemistry, 86, 195-200.  [ISI] [CrossRef] [ChemPort] [PubMed]
Andersson, P. F., Bengtsson, S., Stenlid, J. & Broberg, A. (2012). Molecules, 17, 7769-7781.  [CrossRef] [ChemPort] [PubMed]
Andersson, P. F., Johansson, S. B. K., Stenlid, J. & Broberg, A. (2010). For. Pathol. 40, 43-46.  [ISI] [CrossRef]
Blight, M. M. & Grove, J. F. (1986). J. Chem. Soc. Perkin Trans. 1, pp. 1317-1322.  [CrossRef]
Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brian, P. W., Curtis, P. J., Hemming, H. G. & Norris, G. L. F. (1957). Trans. Br. Mycol. Soc. 40, 365-368.  [CrossRef] [ChemPort]
Brian, P. W. & McGowan, J. C. (1945). Nature, 156, 144-145.  [CrossRef] [ChemPort] [ISI]
Cross, M. J., Stewart, A., Hodgkin, M. N., Kerr, D. J. & Wakelam, M. J. O. (1995). J. Biol. Chem. 270, 25352-25355.  [ChemPort] [PubMed]
Dewick, P. M. (2002). Nat. Prod. Rep. 19, 181-222.  [CrossRef] [PubMed] [ChemPort]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [ISI] [CrossRef] [ChemPort] [details]
Hanson, J. R. (1995). Nat. Prod. Rep. 12, 381-384.  [CrossRef] [ChemPort] [PubMed]
Harrison, D. M. (1990). Nat. Prod. Rep. 7, 459-484.  [CrossRef] [ChemPort] [PubMed]
Jones, R. W. & Hancock, J. G. (1987). Can. J. Microbiol. 33, 963-966.  [CrossRef] [ChemPort] [PubMed]
Lang, Y., Souza, F. E. S., Xu, X., Taylor, N. J., Assoud, A. & Rodrigo, R. (2009). J. Org. Chem. 74, 5429-5439.  [CSD] [CrossRef] [PubMed] [ChemPort]
MacMillan, J., Simpson, T. J., Vanstone, A. E. & Yeboah, S. K. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 2892-2898.  [CrossRef]
Moffatt, J. S., Bu'Lock, J. D. & Yuen, T. H. (1969). J. Chem. Soc. D, p. 839a.
Neidle, S., Rogers, D. & Hursthouse, M. B. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 760-766.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Przybyl, K. (2002). For. Pathol. 32, 387-394.  [ISI] [CrossRef]
Queloz, V., Grunig, C. R., Berndt, R., Kowalski, T., Sieber, T. N. & Holdenrieder, O. (2011). For. Pathol. 41, 133-142.  [ISI] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, A., Blois, J., Yuan, H., Aikawa, E., Ellson, C., Figueiredo, J. L., Weissleder, R., Kohler, R., Yaffe, M. B., Cantley, L. C. & Josephson, L. (2009). Mol. Cancer Ther. 8, 1666-1675.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wipf, P. & Kerekes, A. D. (2003). J. Nat. Prod. 66, 716-718.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o467-o468   [ doi:10.1107/S1600536813005606 ]

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