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Volume 69 
Part 6 
Page o985  
June 2013  

Received 9 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.169
Data-to-parameter ratio = 17.8
Details
Open access

(E)-9-(4-Fluorostyryl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione

aCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
Correspondence e-mail: jhcha@kist.re.kr

In the title compound, C25H27FO3, each of the cyclohexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating by 0.0769 (15) and 0.196 (2) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.004 Å). The C=C double bond adopts an E conformation. The dihedral angle between the benzene and pyran (all atoms) rings is 89.94 (10)°. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains running parallel to the b axis.

Related literature

For the crystal structures of xanthenes derivatives studied recently by our group, see: Cha et al. (2012[Cha, J. H., Pae, A. N., Lee, J. K. & Cho, Y. S. (2012). Acta Cryst. E68, o454.], 2013[Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.]); Lee et al. (2012[Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.]).

[Scheme 1]

Experimental

Crystal data
  • C25H27FO3

  • Mr = 394.48

  • Monoclinic, P 21 /c

  • a = 5.9367 (7) Å

  • b = 18.8521 (16) Å

  • c = 19.3709 (16) Å

  • [beta] = 99.681 (3)°

  • V = 2137.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 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 = 0.773, Tmax = 0.983

  • 20480 measured reflections

  • 4864 independent reflections

  • 2857 reflections with F2 > 2[sigma](F2)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.169

  • S = 1.09

  • 4864 reflections

  • 274 parameters

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22B...O2i 0.96 2.60 3.533 (4) 163
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -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: FF2106 ).


Acknowledgements

Financial 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., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.  [CrossRef] [details]
Cha, J. H., Pae, A. N., Lee, J. K. & Cho, Y. S. (2012). Acta Cryst. E68, o454.  [CSD] [CrossRef] [details]
Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.  [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] [ChemPort] [details]


Acta Cryst (2013). E69, o985  [ doi:10.1107/S1600536813014049 ]

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