(E)-4-(2-Chloro-1-hy­droxy-2,6,6-tri­methyl­cyclo­hex­yl)but-3-en-2-one

Liu, S.; Yang, X.-Y.; Zhang, Y.-L.

doi:10.1107/S1600536812048544

Volume 68
Part 12
Page o3485
December 2012

Received 6 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.068
wR = 0.179
Data-to-parameter ratio = 16.9
Details

(E)-4-(2-Chloro-1-hydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one

Shan Liu,^a ^* Xiao-Yan Yang ^a and Yu-Ling Zhang ^a

^aNanjing College of Chemical Technology, No. 625 Geguan Road, Luhe, Nanjing 210048, People's Republic of China
Correspondence e-mail: dols80@163.com

In the title molecule, C₁₃H₂₁ClO₂, there is an intramolecular C-HCl hydrogen bond. The conformation about the C=C bond is E and the six-membered ring has a chair conformation. In the crystal, molecules are linked by pairs of O-HO hydrogen bonds, forming inversion dimers, which are consolidated by C-HO hydrogen bonds. The dimers are linked via C-H.·O hydrogen bonds, forming chains along [100].

Related literature

For the use of (E)-4-(2-chloro-1-hydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one, see: Sakai et al. (1992). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₃H₂₁ClO₂
M_r = 244.75
Monoclinic, P 2₁ /n
a = 6.266 (1) Å
b = 8.586 (2) Å
c = 24.868 (5) Å
= 92.24 (3)°
V = 1336.9 (5) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.923, T_max = 0.973
2688 measured reflections
2450 independent reflections
1611 reflections with I > 2(I)
R_int = 0.068
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.179
S = 1.00
2450 reflections
145 parameters
1 restraint
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2ⁱ	0.82	2.12	2.858 (3)	149
C7-H7AO2ⁱ	0.96	2.58	3.473 (5)	155
C8-H8CCl	0.96	2.59	3.257 (3)	127
C13-H13CO1ⁱⁱ	0.96	2.59	3.536 (4)	169
Symmetry codes: (i) -x+2, -y, -z; (ii) x-1, y, z.

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: ZJ2098 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sakai, K., Takahashi, K. & Nukano, T. (1992). Tetrahedron, 64, 8229-8238.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds