3-Hy­droxy-8-oxo-3-nor-methyl­chamigrane-2,7-peroxide

Liu, D.

doi:10.1107/S1600536810024517

Volume 66
Part 7
Page o1875
July 2010

Received 1 June 2010
Accepted 23 June 2010
Online 30 June 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 9.6
Details

3-Hydroxy-8-oxo-3-nor-methylchamigrane-2,7-peroxide

Dongze Liu ^a ^*

^aSouth China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, People's Republic of China
Correspondence e-mail: dongzeliu@scsio.ac.cn

In the title compound, C₁₄H₂₂O₄ (systematic name: 9-hydroxy-1,5,5-trimethyl-1,8-epidioxyspiro[5.5]decan-2-one), which was isolated from the fermentation broth of Steccherinum ochraceum, the two six-membered rings adopt chair conformations and are bridged by a peroxide group. The hydroxy H atom forms a three-centre cyclic intermolecular O-H(O,O') hydrogen-bonding interaction with a peroxide and a carbonyl O-atom acceptor, forming [100] chains.

Related literature

For similar structures, see Miyashita et al. (1998).

Experimental

Crystal data

C₁₄H₂₂O₄
M_r = 254.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3138 (4) Å
b = 12.4206 (7) Å
c = 13.9408 (8) Å
V = 1266.41 (12) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 173 K
0.42 × 0.38 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.961, T_max = 0.967
6456 measured reflections
1602 independent reflections
1471 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.08
1602 reflections
167 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1ⁱ	0.84	2.51	3.112 (2)	130
O2-H2AO4ⁱ	0.84	2.17	2.943 (2)	154
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2044 ).

Acknowledgements

This Project was supported by China Postdoctoral Science Foundation (5350209-7-1).

References

Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Miyashita, K. Tanaka, A. Shintaku, H. & Iwata, C. (1998). Tetrahedron, 8, 1395-1406.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds