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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 [sigma](C-C) = 0.004 Å
R = 0.068
wR = 0.179
Data-to-parameter ratio = 16.9
Details
Open access

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

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-H...Cl 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-H...O hydrogen bonds, forming inversion dimers, which are consolidated by C-H...O 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[Sakai, K., Takahashi, K. & Nukano, T. (1992). Tetrahedron, 64, 8229-8238.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H21ClO2

  • Mr = 244.75

  • Monoclinic, P 21 /n

  • a = 6.266 (1) Å

  • b = 8.586 (2) Å

  • c = 24.868 (5) Å

  • [beta] = 92.24 (3)°

  • V = 1336.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 298 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.923, Tmax = 0.973

  • 2688 measured reflections

  • 2450 independent reflections

  • 1611 reflections with I > 2[sigma](I)

  • Rint = 0.068

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.179

  • S = 1.00

  • 2450 reflections

  • 145 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.82 2.12 2.858 (3) 149
C7-H7A...O2i 0.96 2.58 3.473 (5) 155
C8-H8C...Cl 0.96 2.59 3.257 (3) 127
C13-H13C...O1ii 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[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [details]
Sakai, K., Takahashi, K. & Nukano, T. (1992). Tetrahedron, 64, 8229-8238.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3485  [ doi:10.1107/S1600536812048544 ]

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