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Volume 65 
Part 7 
Page o1714  
July 2009  

Received 15 June 2009
Accepted 20 June 2009
Online 27 June 2009

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Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.110
Data-to-parameter ratio = 9.3
Details
Open access

Maleopimaric acid acetic acid solvate

Meng Zhang,a Yong-hong Zhou,a* Xiao-xin Guoa and Li-hong Hua

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, 210042, People's Republic of China
Correspondence e-mail: zm205@sohu.com

The title compound, C24H32O5·C2H4O2, is a derivative of abietic acid. The two fused and unbridged cyclohexane rings have chair conformations and the anhydride ring is planar. Of the other three six-membered rings, two have boat conformations and one has a twist-boat conformation. The crystal structure is stabilized by intermolecular O-H...O and C-H...O hydrogen bonds.

Related literature

For general background, see: McCoy (2000[McCoy, M. (2000). Chem. Eng. News, 78, 13-15.]); Schweizer et al. (2003[Schweizer, R. A. S., Atanasoc, A. G., Frey, B. M. & Odermatt, A. (2003). Mol. Cell. Endocrinol. 212, 41-49.]); Savluchinske-Feio et al. (2007[Savluchinske-Feio, S., Nunes, L., Pereira, P. T., Silva, A. M., Roseiro, J. C., Gigante, B. & Curto, M. J. M. (2007). J. Microbiol. Methods, 70, 465-470.]). For the crystal structure of a similar compound, see: Pan et al. (2006[Pan, Y.-M., Yang, L., Wang, H.-S., Zhao, Z.-C. & Zhang, Y. (2006). Acta Cryst. E62, o5701-o5703.]). For standard 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.]).

[Scheme 1]

Experimental

Crystal data

  • C24H32O5·C2H4O2

  • Mr = 460.55

  • Orthorhombic, P 21 21 21

  • a = 7.9469 (10) Å

  • b = 12.7755 (16) Å

  • c = 24.884 (3) Å

  • V = 2526.3 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 291 K

  • 0.30 × 0.26 × 0.24 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.97, Tmax = 0.98

  • 13853 measured reflections

  • 2837 independent reflections

  • 2432 reflections with I > 2[sigma](I)

  • Rint = 0.059
Refinement

  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.110

  • S = 1.04

  • 2837 reflections

  • 304 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4C...O6 0.93 1.70 2.617 (3) 169
O7-H7A...O5 0.93 1.76 2.681 (3) 171
C13-H13C...O5i 0.96 2.59 3.137 (5) 117
C26-H26B...O1ii 0.96 2.56 3.369 (4) 142
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2334 ).

Acknowledgements

This work was supported by the President of the Chinese Academy of Forestry Foundation (CAFYBB2008009).

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.
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
McCoy, M. (2000). Chem. Eng. News, 78, 13-15.
Pan, Y.-M., Yang, L., Wang, H.-S., Zhao, Z.-C. & Zhang, Y. (2006). Acta Cryst. E62, o5701-o5703.  [CSD] [CrossRef] [details]
Savluchinske-Feio, S., Nunes, L., Pereira, P. T., Silva, A. M., Roseiro, J. C., Gigante, B. & Curto, M. J. M. (2007). J. Microbiol. Methods, 70, 465-470.  [ISI] [CrossRef] [PubMed] [ChemPort]
Schweizer, R. A. S., Atanasoc, A. G., Frey, B. M. & Odermatt, A. (2003). Mol. Cell. Endocrinol. 212, 41-49.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2009). E65, o1714  [ doi:10.1107/S1600536809023745 ]

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