(E)-1-(2,4-Dihy­droxy­phen­yl)-3-(4-hydroxy­phen­yl)prop-2-en-1-one monohydrate

Jian-Guo Wang; Lin Wu; Chan-Juan Zhong; Zhao-Hui Ouyang; De-Lian Yi

doi:10.1107/S1600536811006271

. 2011 Feb 26;67(Pt 3):o732. doi: 10.1107/S1600536811006271

(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one monohydrate

Jian-Guo Wang ^a,^b,^*, Lin Wu ^a, Chan-Juan Zhong ^b, Zhao-Hui Ouyang ^a, De-Lian Yi ^a

PMCID: PMC3052009 PMID: 21522472

Abstract

In the title compound, C₁₅H₁₂O₄·H₂O, the two benzene rings are not coplanar, making a dihedral angle of 7.24 (16)°. An intramolecular hydroxy–carbonyl O—H⋯O hydrogen bond occurs. In the crystal, four intermolecular O—H⋯O hydrogen bonds involving the hydroxy residues, the carbonyl group and the water molecule lead to the formation of a three-dimensional network. The supramolecular structure is further stabilized by weak C—H⋯O interactions.

Related literature

For the biological activity of the title compound, see: Jang et al. (2008 ▶); Liu et al. (2008 ▶). For a related structure, see: Ma et al. (2005 ▶). graphic file with name e-67-0o732-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₂O₄·H₂O
M _r = 274.26
Monoclinic,
a = 11.489 (2) Å
b = 9.5903 (17) Å
c = 12.498 (2) Å
β = 103.649 (3)°
V = 1338.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.988, T _max = 0.990
8297 measured reflections
2625 independent reflections
2115 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.144
S = 1.09
2625 reflections
196 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006271/go2004sup1.cif

e-67-0o732-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006271/go2004Isup2.hkl

e-67-0o732-Isup2.hkl^{(128.9KB, hkl)}

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

Enhanced figure: interactive version of Fig. 1

Enhanced figure: interactive version of Fig. 2

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3	0.87 (2)	1.74 (2)	2.530 (2)	150 (3)
O2—H2A⋯O5ⁱ	0.82 (2)	1.83 (2)	2.644 (3)	175 (4)
O4—H4A⋯O3ⁱⁱ	0.83 (2)	1.95 (2)	2.776 (2)	175 (4)
O5—H5A⋯O1ⁱⁱⁱ	0.84 (2)	1.99 (2)	2.802 (2)	164 (3)
O5—H5B⋯O4^iv	0.84 (2)	1.97 (2)	2.785 (3)	165 (3)
C9—H9⋯O4^v	0.93	2.56	3.402 (3)	151

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This study was funded by the Jiangxi Provincial Department of Education (GJJ08433) and the Jiangxi Provincial Department of Science and Technology (2008ZD06100). The authors thank Professor Xianggao Meng at Hua-Zhong Normal University for the data acquisition.

supplementary crystallographic information

Comment

The title compound exhibits many biological activities such as tracheal relaxation effects (Liu et al., 2008) and suppressing cocaine-induced extracellular dopamine release (Jang et al., 2008).

One (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one molecule bears one crystalline water molecule (Fig.1). In the molecule, the two benzene rings are not coplanar, the dihedral angle being 7.24 (16)°. The structure displays O—H···O and C—H···O hydrogen bonding (Table 1 and Fig. 2).

Experimental

2, 4-dihydroxyacetophenone (7.6 g, 0.05 mol) and 4-hydroxybenzaldehyde (8.54 g, 0.07 mol) were dissolved in diglycol (25 ml). Then 40% aq. KOH (50 ml) was added, and the reaction mixture was vigorously stirred under nitrogen atmosphere at 333 K for 2 h. The progress of the reaction was monitored by thin- layer chromatography (Si gel, developing solvent V(ethyl acetate)/V(benzene) = 1:2). The mixture was colled to room temperature and 1:1 (v/v) hydrochloric acid was added to acidize the mixture to pH=3 and a solid was obtained. After crystallized by ethanol-water, crystalline yellow needles were obtained, m.p. 472.5–474.2 K.