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Volume 69 
Part 10 
Page o1542  
October 2013  

Received 2 September 2013
Accepted 9 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.194
Data-to-parameter ratio = 18.4
Details
Open access

9-[(E)-2-(4-Chlorophenyl)ethenyl]-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul, 136-791, South Korea,bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul, 136-791, South Korea, and cDrug Discovery Platform Technology Team, Korea Research Institute, of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, South Korea
Correspondence e-mail: j9601@kist.re.kr

In the title compound, C25H27ClO3, each of the cyclohexenone rings adopts an envelope conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. The C=C double bond is in the trans conformation. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains running parallel to the b axis.

Related literature

For the synthesis and the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2013[Cha, J. H., Lee, J. K., Min, S.-J., Cho, Y. S. & Park, J. (2013). Acta Cryst. E69, o1347.]); Lee et al. (2012[Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.], 2013[Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Won, S. O. (2013). Acta Cryst. E69, o985.]).

[Scheme 1]

Experimental

Crystal data
  • C25H27ClO3

  • Mr = 410.94

  • Monoclinic, P 21 /n

  • a = 5.9686 (4) Å

  • b = 18.7567 (13) Å

  • c = 20.1089 (13) Å

  • [beta] = 100.9322 (18)°

  • V = 2210.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 296 K

  • 0.40 × 0.10 × 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 = 0.629, Tmax = 0.981

  • 21185 measured reflections

  • 5042 independent reflections

  • 2842 reflections with F2 > 2.0[sigma](F2)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.194

  • S = 1.11

  • 5042 reflections

  • 274 parameters

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

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C23-H23B...O2i 0.96 2.53 3.461 (4) 163
Symmetry code: (i) [-x+{\script{5\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: FF2119 ).


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., Lee, J. K., Min, S.-J., Cho, Y. S. & Park, J. (2013). Acta Cryst. E69, o1347.  [CSD] [CrossRef] [IUCr Journals]
Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Won, S. O. (2013). Acta Cryst. E69, o985.  [CSD] [CrossRef] [IUCr Journals]
Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.  [CSD] [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, o1542  [ doi:10.1107/S1600536813025026 ]

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