(E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­(3-hy­droxy­cyclo­hex-2-en-1-one)

Cha, J.H.; Kim, Y.H.; Lee, J.K.; Cho, Y.S.

doi:10.1107/S1600536811054730

Volume 68
Part 1
Page o245
January 2012

Received 8 December 2011
Accepted 19 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.156
Data-to-parameter ratio = 12.9
Details

(E)-2,2'-[3-(2-Nitrophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxycyclohex-2-en-1-one)

Joo Hwan Cha,^a ^* Young Hee Kim,^b Jae Kyun Lee ^b and Yong Seo Cho ^b

^aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and ^bCenter for Neuro-Medicine, 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, C₂₁H₂₁NO₆, each of the cyclohexenone rings adopts a half-chair conformation. Each of the pairs of hydroxy and carbonyl O atoms are oriented to allow for the formation of intramolecular O-HO hydrogen bonds, which are typical of xanthene derivatives.

Related literature

For the biological activity xanthenes and their derivatives and for related structures, see: Lee et al. (2011).

Experimental

Crystal data

C₂₁H₂₁NO₆
M_r = 383.40
Monoclinic, P 2₁ /n
a = 8.0785 (7) Å
b = 8.7261 (6) Å
c = 26.2616 (17) Å
= 90.829 (3)°
V = 1851.1 (3) Å³
Z = 4
Mo K radiation
= 0.10 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 = 0.739, T_max = 0.990
14705 measured reflections
3387 independent reflections
2335 reflections with F² > 2(F²)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.156
S = 1.14
3387 reflections
263 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O3	0.82	1.83	2.627 (2)	164
O4-H4O1	0.82	1.78	2.579 (2)	165

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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: FF2047 ).

Acknowledgements

This work was supported financially by a grant from the Korea Institute of Science and Technology (KIST).

References

Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.
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