2-{(1S,2S,4aR,8R,8aR)-8-Hy­droxy-4a,8-dimethyl-1-[(2E)-2-methyl­but-2-eno­yl­oxy]perhydro­naphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis

Kheyrabadi, R.; Habibi, Z.; Ng, S.W.

doi:10.1107/S1600536811037640

Volume 67
Part 10
Page o2699
October 2011

Received 13 September 2011
Accepted 15 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.028
wR = 0.076
Data-to-parameter ratio = 15.4
Details

2-{(1S,2S,4aR,8R,8aR)-8-Hydroxy-4a,8-dimethyl-1-[(2E)-2-methylbut-2-enoyloxy]perhydronaphthalen-2-yl}acrylic acid from Sclerorhachis platyrachis

Rasool Kheyrabadi,^a Zohreh Habibi ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Shahid Beheshti University, General Campus, Tehran, Iran,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

The eudesmane-type terpenoid, C₂₀H₃₀O₅, isolated from Sclerorhachis platyrachis, has a decalin skeleton whose six-membered rings adopt chair conformations. The two methyl substituents occupy axial positions, whereas the other three substituents occupy equatorial positions. The hydroxy group is an intramolecular hydrogen-bond donor to the single-bond ester O atom; adjacent molecules are linked through the carboxylic acid interacting with the hydroxyl group, forming a hydrogen-bonded chain running along the c axis.

Related literature

For the crystal structure of epiilic acid, see: Daniewski et al. (1986). For a review of eudesmane-type sesquiterpenoids, see: Wu et al. (2006).

Experimental

Crystal data

C₂₀H₃₀O₅
M_r = 350.44
Monoclinic, P 2₁
a = 6.2718 (1) Å
b = 19.0285 (3) Å
c = 8.4530 (2) Å
= 110.184 (2)°
V = 946.85 (3) Å³
Z = 2
Cu K radiation
= 0.71 mm^-1
T = 100 K
0.20 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.872, T_max = 0.872
5962 measured reflections
3663 independent reflections
3635 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.076
S = 1.03
3663 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.13 e Å^-3
Absolute structure: Flack (1983), 1705 Friedel pairs
Flack parameter: 0.08 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O5ⁱ	0.85 (2)	1.80 (2)	2.648 (1)	174 (2)
O5-H5O3	0.85 (2)	1.99 (2)	2.692 (1)	139 (2)
Symmetry code: (i) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2330 ).

Acknowledgements

The authors thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Daniewski, W. M., Kroszcznski, W., Bloszyk, E., Drozdz, B., Nawrot, J., Rychlewska, U., Budesinsky, M. & Holub, M. (1986). Collect. Czech. Chem. Commun. 51, 1710-1721.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Wu, Q.-X., Shi, Y.-P. & Jia, Z.-J. (2006). Nat. Prod. Rep. 23, 699-734.

organic compounds