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Volume 69 
Part 8 
Page o1347  
August 2013  

Received 13 July 2013
Accepted 23 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.135
Data-to-parameter ratio = 18.4
Details
Open access

(E)-2,2'-[3-(4-Chlorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea,bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and cCorporated R&D Center, Duksan Hi-Metal Co. Ltd., Cheonan-si 331-821, Republic of Korea
Correspondence e-mail: j9601@kist.re.kr

The title compound, C25H29ClO4, adopts a trans conformation about the C=C double bond and the dimethylcyclohexenone rings both show an envelope conformation with the dimethyl-substituted C atom as the flap. In the molecule, the hydroxy and carbonyl groups form two intramolecular O-H...O hydrogen bonds typical for xanthene derivatives. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains running parallel to the a-axis direction.

Related literature

For the crystal structures of xanthene derivatives studied recently our group, see: Cha et al. (2011[Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.], 2012[Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.], 2013[Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.]).

[Scheme 1]

Experimental

Crystal data
  • C25H29ClO4

  • Mr = 428.95

  • Monoclinic, C 2/c

  • a = 25.8781 (16) Å

  • b = 9.7820 (6) Å

  • c = 20.9904 (11) Å

  • [beta] = 121.2919 (15)°

  • V = 4540.5 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 296 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.692, Tmax = 0.962

  • 21331 measured reflections

  • 5175 independent reflections

  • 3926 reflections with F2 > 2[sigma](F2)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.135

  • S = 1.08

  • 5175 reflections

  • 281 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1 0.82 1.78 2.596 (2) 173
O4-H4...O3 0.82 1.87 2.669 (2) 166
C18-H18...O2i 0.93 2.51 3.418 (3) 165
C21-H21...O3ii 0.93 2.61 3.397 (3) 143
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2113 ).


Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.  [CSD] [CrossRef] [IUCr Journals]
Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.  [CSD] [CrossRef] [IUCr Journals]
Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.  [CrossRef] [IUCr Journals]
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1347  [ doi:10.1107/S1600536813020357 ]

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