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Volume 69 
Part 3 
Page o397  
March 2013  

Received 8 February 2013
Accepted 14 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.158
Data-to-parameter ratio = 18.0
Details
Open access

(E)-2,2'-[3-(4-Fluorophenyl)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

In the title compound, C25H29FO4, each cyclohexenone ring has an envelope conformation with the dimethyl-substituted atom as the flap. The hydroxy and carbonyl groups form two intramolecular O-H...O hydrogen bonds, as is typical for xanthene derivatives. In the crystal, very weak C-H...O hydrogen bonds link molecules into dimers.

Related literature

For the crystal structures of related xanthenes derivatives, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C25H29FO4

  • Mr = 412.50

  • Monoclinic, C 2/c

  • a = 26.1146 (13) Å

  • b = 9.6961 (4) Å

  • c = 20.5638 (9) Å

  • [beta] = 121.5921 (15)°

  • V = 4435.3 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.771, Tmax = 0.991

  • 21193 measured reflections

  • 5070 independent reflections

  • 3370 reflections with F2 > 2[sigma](F2)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.158

  • S = 1.09

  • 5070 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O4 0.82 1.78 2.582 (2) 168
O3-H3...O2 0.82 1.85 2.652 (3) 168
C9-H9...O1i 0.93 2.62 3.353 (3) 136
C16-H16...O4i 0.93 2.62 3.499 (3) 158
Symmetry code: (i) [-x+1, y, -z+{\script{1\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: CV5387 ).


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.  [ISI] [CrossRef] [ChemPort] [details]
Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.  [CSD] [CrossRef] [details]
Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.  [CSD] [CrossRef] [details]
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] [details]


Acta Cryst (2013). E69, o397  [ doi:10.1107/S1600536813004364 ]

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