(IUCr) 8-Methyl-5-methylene-2-oxotricyclo[5.3.1.13,9]dodecan-endo-8-ol

Volume 64
Part 5
Page o841
May 2008

Received 7 April 2008
Accepted 8 April 2008
Online 16 April 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R = 0.049
wR = 0.053
Data-to-parameter ratio = 14.3
Details

8-Methyl-5-methylene-2-oxotricyclo[5.3.1.1^3,9]dodecan-endo-8-ol

Isa Y. H. Chan,^a Roger Bishop,^a Donald C. Craig,^a Marcia L. Scudder ^a ^* and Weimin Yue ^b

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia, and ^bSchool of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China
Correspondence e-mail: m.scudder@unsw.edu.au

The title compound, C₁₄H₂₀O₂, crystallizes with homochiral chains of molecules hydrogen bonded together along the b axis. Adjacent chains in the ab plane contain molecules of the same chirality, leading to a chiral segregation of the molecules into layers.

Related literature

For related literature, see: Yue et al. (2002, 2006, 2007, 1997, 2000).

Experimental

Crystal data

C₁₄H₂₀O₂
M_r = 220.3
Monoclinic, P 2₁ /c
a = 7.554 (3) Å
b = 13.196 (3) Å
c = 12.597 (5) Å
= 108.16 (2)°
V = 1193.2 (7) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 294 K
0.25 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
2247 measured reflections
2079 independent reflections
1296 reflections with I > 2(I)
R_int = 0.016
1 standard reflection frequency: 30 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.052
S = 1.27
2079 reflections
145 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1O2ⁱ	1.00	1.87	2.867 (4)	180
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (Palmer, 2005); software used to prepare material for publication: local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2391 ).

Acknowledgements

This research was supported by the Australian Research Council and the Shanghai Pujiang Program (WY).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Palmer, D. (2005). CrystalMaker. CrystalMaker Software Ltd, Yarnton, Oxfordshire, England. http://www.CrystalMaker.co.uk.
Rae, A. D. (2000). RAELS. Australian National University, Canberra, Australia.
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2000). Tetrahedron, 56, 6667-6673.
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2002). CrystEngComm, 4, 591-595.
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2007). Acta Cryst. E63, o4689.
Yue, W., Bishop, R., Scudder, M. L. & Craig, D. C. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 2937-2946.
Yue, W., Nakano, K., Bishop, R., Craig, D. C., Harris, K. D. M. & Scudder, M. L. (2006). CrystEngComm, 8, 250-256.

organic compounds

8-Methyl-5-methylene-2-oxotricyclo[5.3.1.13,9]dodecan-endo-8-ol