Dehydro­abietic acid

Rao, X.-P.; Song, Z.-Q.; Shang, S.-B.

doi:10.1107/S1600536809035600

Volume 65
Part 10
Page o2402
October 2009

Received 25 August 2009
Accepted 3 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R = 0.077
wR = 0.182
Data-to-parameter ratio = 9.5
Details

Dehydroabietic acid

Xiao-Ping Rao,^a ^* Zhan-Qian Song ^a and Shi-Bin Shang ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
Correspondence e-mail: rxping2001@163.com

The title compound [systematic name: (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid], C₂₀H₂₈O₂, has been isolated from disproportionated rosin which is obtained by isomerizing gum rosin with a Pd-C catalyst.. Two crystallographically independent molecules exist in the asymmetric unit. In each molecule, there are three six-membered rings, which adopt planar, half-chair and chair conformations. The two cyclohexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by intermolecular O-HO hydrogen bonds.

Related literature

For the synthesis and uses of dehydroabietic acid, see: Halbrook & Lawrence (1966); Jia et al. (2009); Piispanen et al. (2001); Rao et al. (2006); Rao, Song & He (2008); Rao, Song, He & Jia (2008); Sepulveda et al. (2005); Wada et al. (1985).

Experimental

Crystal data

C₂₀H₂₈O₂
M_r = 300.42
Monoclinic, P 2₁
a = 11.738 (2) Å
b = 11.875 (2) Å
c = 13.654 (3) Å
= 107.50 (3)°
V = 1815.1 (6) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 293 K
0.40 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (XCAD4; Harms & Wocadlo, 1995) T_min = 0.973, T_max = 0.986
3592 measured reflections
3417 independent reflections
2173 reflections with I > 2(I)
R_int = 0.086
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.182
S = 1.00
3417 reflections
361 parameters
3 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2DO3ⁱ	0.82	1.82	2.621 (8)	165
O4-H4AO1ⁱⁱ	0.82	1.79	2.598 (8)	168
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2868 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 30800871) and the Fundamental Research Foundation of the Central Commonwealth Institute of the Chinese Academy of Forestry (grant No. CAFYBB2008021),

References

Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Halbrook, N. J. & Lawrence, R. V. (1966). J. Org. Chem. 31, 4246-4247.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jia, W. H., Rao, X. P., Song, Z. Q. & Shang, S. B. (2009). J. Surf. Det. 12, 261-267. .
Piispanen, P. S., Hedman, B. & Norin, T. (2001).J. Surf. Det. 5, 165-168..
Rao, X. P., Song, Z. Q. & He, L. (2008). Heteroat. Chem. 19, 512-516.
Rao, X. P., Song, Z. Q., He, L. & Jia, W. H. (2008). Chem. Pharm. Bull. 56, 1575-1578.
Rao, X.-P., Song, Z.-Q., Radbil, B. & Radbil, A. (2006). Acta Cryst. E62, o5301-o5302.
Sepulveda, B., Astudillo, L., Rodriguez, J., Yanez, T., Theoduloz, C. & Schmeda, G. (2005). Pharmacol. Res. 52, 429-437.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wada, H., Kodato, S., Kawamori, M., Morikawa, T., Nakai, H., Takeda, M., Saito, S., Onoda, Y. & Tamaki, H. (1985). Chem. Pharm. Bull. (Tokyo), 33, 1472-1487.

organic compounds