3-Hy­droxy-2-[(2E)-1-(2-hy­droxy-6-oxocyclo­hex-1-en-1-yl)-3-(2-meth­oxy­phen­yl)prop-2-en-1-yl]cyclo­hex-2-en-1-one

Joo Hwan Cha; Myung Hee Son; Sun-Joon Min; Yong Seo Cho; Jae Kyun Lee

doi:10.1107/S1600536811038207

. 2011 Sep 30;67(Pt 10):o2739. doi: 10.1107/S1600536811038207

3-Hydroxy-2-[(2E)-1-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-3-(2-methoxyphenyl)prop-2-en-1-yl]cyclohex-2-en-1-one

Joo Hwan Cha ^a, Myung Hee Son ^b, Sun-Joon Min ^b, Yong Seo Cho ^b, Jae Kyun Lee ^b,^*

PMCID: PMC3201272 PMID: 22065620

Abstract

In the title compound, C₂₂H₂₄O₅, each of the cyclohexenone rings adopts a half-chair conformation. The hydroxy and carbonyl O atoms face each other and are orientated to allow for the formation of the two intramolecular O—H⋯O hydrogen bonds which are typical of xanthene derivatives. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into layers parallel to the ab plane.

Related literature

For the biological activity of xanthenes and their derivatives, see: Jonathan et al. (1988 ▶); Delfourne et al. (2000 ▶); Koeller et al. (2003 ▶); For related xanthene structures, see: Bolte et al. (2001 ▶); Palakshi Reddy et al. (2010 ▶).

Experimental

Crystal data

C₂₂H₂₄O₅
M _r = 368.43
Monoclinic,
a = 10.7988 (8) Å
b = 12.0509 (8) Å
c = 15.0238 (10) Å
β = 104.536 (2)°
V = 1892.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 297 K
0.40 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T _min = 0.715, T _max = 0.982
18125 measured reflections
4304 independent reflections
2465 reflections with F ² > 2.0σ(F ²)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.119
S = 1.05
4304 reflections
255 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038207/cv5143sup1.cif

e-67-o2739-sup1.cif^{(35.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038207/cv5143Isup2.hkl

e-67-o2739-Isup2.hkl^{(210.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038207/cv5143Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5	0.82	1.85	2.644 (3)	163
O4—H4A⋯O2	0.82	1.80	2.594 (3)	162
C19—H19A⋯O4ⁱ	0.97	2.49	3.272 (3)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

supplementary crystallographic information

Comment

Xanthenes constitute an important class of organic compounds that have attracted strong interest due to their useful biological and pharmacological properties, such as antibacterial, antiviral and antiinflammatory activities (Jonathan et al., 1988). They also constitute a structural unit of a series of natural products (Delfourne et al., 2000). Also they are being developed to act as new clinical agents in cancer therapy (Koeller et al., 2003). Herewith we present the crystal structure of the title compound (I) (Fig. 1), which is a Xanthene derivative.

The molecular structure of xanthenedione features two cyclohexene rings, each has a half-chair conformation and lie above the respective least-squares plane through the remaining five carbon atoms (Palakshi Reddy et al., 2010). Bolte and colleagues determined the crystal structures of bis-dimedone derivatives which showed nearly the same packing pattern irrespective of the different substituent in the para position of the aromatic ring (Bolte et al., 2001). Two cyclohexenone rings in (I) display envelope conformation, and atoms C14 and C19 are directed towards the aromatic ring. The hydroxy and carbonyl O atoms face each other and are orientated to allow for the formation of two intramolecular O—H···O hydrogen bonds (Table 1) typical for Xanthene derivative.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) links the molecules into layers parallel to ab plane.

Experimental

To solution of 1,3-cyclohexanedione (4.68 mmol), 2-methoxycinnamaldehyde (1.87 mmol) and 4Å MS was added catalytic amounts of L-proline (0.47 mmol) in under nitrogen atmosphere. After stirring for 5 h, the anhydrous ethyl acetate (0.5 ml) was added to a reaction mixture and the solution was stirred for 2 days. The reaction mixture was filtered through pad of celite to remove MS and concentrated. The residue oil was purified by flash column chromatography to afford product which was recrystallized from ethanol to give crystals suitable for X-ray analysis.