(1RS,2RS,3SR,5RS,7RS)-2,5-Dichloro-8-oxabicyclo­[5.1.0]octan-3-ol

Çetinkaya, Y.; Menzek, A.; Hökelek, T.

doi:10.1107/S1600536811013304

Volume 67
Part 5
Page o1145
May 2011

Received 25 March 2011
Accepted 8 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.008 Å
R = 0.088
wR = 0.190
Data-to-parameter ratio = 15.7
Details

(1RS,2RS,3SR,5RS,7RS)-2,5-Dichloro-8-oxabicyclo[5.1.0]octan-3-ol

Yasin Çetinkaya,^a Abdullah Menzek ^a and Tuncer Hökelek ^b ^*

^aDepartment of Chemistry, Atatürk University, 25240 Erzurum, Turkey, and ^bDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C₇H₁₀Cl₂O₂, the seven-membered ring displays a chair conformation. In the crystal, the hydroxy H atom is equally disordered over two orientations, and links with an adjacent molecule via an O-HO hydrogen bond in both cases. Weak intermolecular C-HO hydrogen bonding is also a feature of the crystal structure.

Related literature

For background to syn-bis-epoxides, see: Balci (1981); Akbulut et al. (1987); Menzek & Balci (1993); Saraçoglu et al. (1999). For background to unsaturated bicyclic endopexide, see: Menzek et al. (2005). For background to epoxide and bis-epoxide, see: Sengül et al. (2008).

Experimental

Crystal data

C₇H₁₀Cl₂O₂
M_r = 197.05
Orthorhombic, P b c n
a = 21.9202 (5) Å
b = 9.9343 (3) Å
c = 8.1005 (2) Å
V = 1763.98 (8) Å³
Z = 8
Mo K radiation
= 0.68 mm^-1
T = 294 K
0.32 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (Blessing, 1995) T_min = 0.845, T_max = 0.900
32813 measured reflections
1801 independent reflections
1267 reflections with I > 2(I)
R_int = 0.110

Refinement

R[F² > 2(F²)] = 0.088
wR(F²) = 0.190
S = 1.18
1801 reflections
115 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO2ⁱ	0.83 (11)	1.96 (11)	2.746 (7)	159 (12)
O2-H2BO2ⁱⁱ	0.85	1.84	2.692 (8)	174
C2-H21O1ⁱⁱⁱ	0.97	2.43	3.398 (7)	172
Symmetry codes: (i) -x+1, -y+2, -z; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5182 ).

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for the use of X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

Akbulut, N., Menzek, A. & Balci, M. (1987). Tetrahedron Lett. 28, 1689-1692.
Balci, M. (1981). Chem. Rev. 81, 91-108.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Menzek, A. & Balci, M. (1993). Aust. J. Chem. 46, 1613-1621.
Menzek, A., Sengül, M. E., Çetinkaya, Y. & Ceylan, S. (2005). J. Chem. Res. pp. 209-214.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Saraçoglu, N., Menzek, A., Sayan, S., Salzner, U. & Balci, M. (1999). J. Org. Chem. 64, 6670-6676.
Sengül, M. E., Menzek, A., Sahin, E., Arik, M. & Saracoglu, N. (2008). Tetrahedron, 64, 7289-7294.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds