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

Cha, J.H.; Min, S.-J.; Cho, Y.S.; Lee, J.K.; Park, J.

doi:10.1107/S1600536813004364

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 (C-C) = 0.003 Å
R = 0.048
wR = 0.158
Data-to-parameter ratio = 18.0
Details

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

Joo Hwan Cha,^a Sun-Joon Min,^b Yong Seo Cho,^b Jae Kyun Lee ^b ^* and Junghwan Park ^c

^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-HO hydrogen bonds, as is typical for xanthene derivatives. In the crystal, very weak C-HO hydrogen bonds link molecules into dimers.

Related literature

For the crystal structures of related xanthenes derivatives, see: Cha et al. (2011, 2012).

Experimental

Crystal data

C₂₅H₂₉FO₄
M_r = 412.50
Monoclinic, C 2/c
a = 26.1146 (13) Å
b = 9.6961 (4) Å
c = 20.5638 (9) Å
= 121.5921 (15)°
V = 4435.3 (4) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.771, T_max = 0.991
21193 measured reflections
5070 independent reflections
3370 reflections with F² > 2(F²)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.158
S = 1.09
5070 reflections
281 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO4	0.82	1.78	2.582 (2)	168
O3-H3O2	0.82	1.85	2.652 (3)	168
C9-H9O1ⁱ	0.93	2.62	3.353 (3)	136
C16-H16O4ⁱ	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); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); 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.
Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.
Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.
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.

organic compounds