(3E,5E)-3,5-Bis(4-hy­droxy­benzyl­idene)oxan-4-one

Du, Z.-Y.; Huang, H.-R.; Lu, Y.-J.; Zhang, K.; Fang, Y.-X.

doi:10.1107/S1600536810051457

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o116

https://doi.org/10.1107/S1600536810051457

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(3E,5E)-3,5-Bis(4-hydroxybenzylidene)oxan-4-one

Zhi-Yun Du,^a Hua-Rong Huang,^a ^* Yu-Jun Lu,^a Kun Zhang ^a and Yan-Xiong Fang ^a

^aGuangdong University of Technology, Faculty of Chemical Engineering and Light Industry, Guangzhou 510006, Guangdong, People's Republic of China
^*Correspondence e-mail: corihhr@yahoo.cn

(Received 9 October 2010; accepted 8 December 2010; online 11 December 2010)

In the title compound, C₁₉H₁₆O₄, there are two 4-hydroxybenzyl substituents on the oxan-4-one (tetrahydropyran-4-one) ring, which exhibits an envelope conformation. The dihedral angles between pyranone ring and the two benzene rings are 26.69 (9) and 36.01 (9)° while the benzene rings make a dihedral angle of 20.88 (10)°. In the crystal, molecules are linked by intermolecular O—H⋯O hydrogen bonds into a supramolecular three-dimensional twofold interpenetrating hydrogen-bonded network.

Related literature

For the pharmacological activity or curcumin [systematic name (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione], see: Maheshwari et al. (2006 ). For curcumin analogues, see: Liang et al. (2009 ). For the synthesis of the title compound, see: Youssef et al. (2004 ); Du et al. (2006 ). For related structures, see: Abaee et al. (2008 ); Du et al. (2006).

Experimental

Crystal data

C₁₉H₁₆O₄
M_r = 308.32
Orthorhombic, P b c a
a = 11.812 (3) Å
b = 7.4687 (16) Å
c = 33.233 (7) Å
V = 2931.9 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.42 × 0.37 × 0.29 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.972
16659 measured reflections
3224 independent reflections
1941 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.04
3224 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	1.95	2.757 (2)	167
O4—H4⋯O1ⁱⁱ	0.82	1.86	2.677 (2)	171
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051457/jh2219sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051457/jh2219Isup2.hkl

checkCIF report

Comment top

For thousands of years Eastern medicine has used curcumin, the major component of turmeric, for a wide range of health benefits, but only in recent times has its biological action been understood. Curcumin possesses a wide spectrum of pharmacological activities including anti-oxidant, anti-inflammatory, antiviral, antifungal, cancer chemo preventive, cancer chemotherapeutic properties (Maheshwari et al., 2006). As the limitation of solubility, stability and activity of curcumin for clinical application, many series of curcumin analoges with a monoketone function have attracted interests in trial of improving the properties (Liang et al., 2009). This class of compounds is readily synthesized by reacting a substituted benzaldehyde with tetrahydropyran-4-one; in the case of the title compound 4-hydroxybenzaldehyde was used as the reactant.

The compound was purified by re-crystallization from THF and characterized by NMR spectrum and ESI mass spectrum. The analytical and spectroscopic data are consistent with the proposed structure given in Scheme 1. The molecular structure of the title compound contains the two 4-methylbenzyl substituents on the tetrahydropyran-4-one and the six-member ring adopts an envelope conformation with the flap oxygen atom displaced by 0.648 (8) Å from the plane of the other five atoms (Figure 1).

Similar structures have been observed in the literature (Abaee et al., 2008; Du et al.,2006).

The dihedral angles formed between the mean plane through the six atoms of the pyranone ring and two benzene rings of 4-methylbenzyl groups are 26.69 (9) and 36.01 (9)°, the corresponding dihedral angles between two benzene rings of 4-methylbenzyl groups is 20.88 (10) °.

In the crystal packing, intermolecular O—H···O hydrogen bonds (Figure 2, table 1) connect the molecules into a supramolecular three-dimensional two-fold interpenetrating hydrogen bonding network (Figure 3).

Related literature top

For the pharmacological activity or curcumin, see: Maheshwari et al. (2006). For curcumin alalogues, see: Liang et al. (2009). For the synthesis of the title compound, see: Youssef et al. (2004); Du et al. (2006). For related structures, see: Abaee et al. (2008); Du et al. (2006).

Experimental top

The title compound was synthesized using a general procedure (Du et al.,2006; Youssef et al., 2004) 4-hydroxybenzaldehyde (0.01 mol) and tetrahydropyran-4-one (0.005 mol) were dissolved in THF and added 0.5 mL concentrated HCl as catalyst. The mixture was warmed at 298-303 K for 12 h, cold water was added to precipitate the yellow compound. Crystals were obtained by recrystallization from THF. The formulation was established by the NMR spectrum and ESI mass spectrum. ¹H NMR (MSDO-d⁶, 300 MHz) δ (ppm): 10.03 (brs, 2H, -COH), 7.55 (s, 2H, -CCH=), 7.28 (d, J = 8.1, 4H, ArH), 6.85 (d, J = 8.1, ArH), 4.85 (s, 4H, -CCH₂-O-CCH₂-C). The ESI mass spectrum showed ions at 308.

Structure description top

Similar structures have been observed in the literature (Abaee et al., 2008; Du et al.,2006).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Hydrogen bonds of the title compound via the O—H···O are shown as dashed lines. Symmetry: A = -x + 2, y - 1/2, -z + 3/2; B = -x + 3/2, -y + 2, z -1/2; C = -x + 2, y + 1/2, -z + 3/2; D = -x + 3/2, -y + 2, z + 1/2.
	Fig. 3. Crystal packing of the title compound, viewed along the b axis, showing the three dimensional two-fold interpenetrating hydrogen bonding network. Dashed lines indicate hydrogen bonds.

(3E,5E)-3,5-Bis(4-hydroxybenzylidene)oxan-4-one top

Crystal data top

C₁₉H₁₆O₄	F(000) = 1296
M_r = 308.32	D_x = 1.397 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3683 reflections
a = 11.812 (3) Å	θ = 2.5–26.7°
b = 7.4687 (16) Å	µ = 0.10 mm⁻¹
c = 33.233 (7) Å	T = 293 K
V = 2931.9 (11) Å³	Block, colourless
Z = 8	0.42 × 0.37 × 0.29 mm

Data collection top

Bruker SMART CCD 1K area-detector diffractometer	3224 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 27.1°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
T_min = 0.960, T_max = 0.972	k = −8→9
16659 measured reflections	l = −42→40

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0545P)² + 0.5774P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3224 reflections	Δρ_max = 0.17 e Å⁻³
211 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (5)

Crystal data top

C₁₉H₁₆O₄	V = 2931.9 (11) Å³
M_r = 308.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.812 (3) Å	µ = 0.10 mm⁻¹
b = 7.4687 (16) Å	T = 293 K
c = 33.233 (7) Å	0.42 × 0.37 × 0.29 mm

Data collection top

Bruker SMART CCD 1K area-detector diffractometer	3224 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1941 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.972	R_int = 0.053
16659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.04	Δρ_max = 0.17 e Å⁻³
3224 reflections	Δρ_min = −0.18 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.91919 (16)	0.7445 (3)	0.61879 (5)	0.0348 (4)
C2	0.88020 (14)	0.8252 (2)	0.58058 (5)	0.0322 (4)
C3	0.79877 (16)	0.9793 (3)	0.58346 (5)	0.0374 (5)
H3A	0.8083	1.0564	0.5602	0.045*
H3B	0.7219	0.9337	0.5831	0.045*
C4	0.79701 (16)	0.9771 (3)	0.65410 (5)	0.0374 (5)
H4A	0.7206	0.9298	0.6536	0.045*
H4B	0.8042	1.0530	0.6776	0.045*
C5	0.87964 (15)	0.8251 (2)	0.65713 (5)	0.0323 (4)
C6	0.92068 (15)	0.7571 (3)	0.54608 (5)	0.0342 (4)
H6	0.9721	0.6642	0.5496	0.041*
C7	0.89904 (14)	0.8015 (2)	0.50413 (5)	0.0327 (4)
C8	0.97612 (15)	0.7402 (3)	0.47550 (6)	0.0386 (5)
H8	1.0364	0.6693	0.4839	0.046*
C9	0.96621 (15)	0.7811 (3)	0.43528 (6)	0.0404 (5)
H9	1.0188	0.7372	0.4169	0.048*
C10	0.87774 (16)	0.8876 (3)	0.42219 (6)	0.0395 (5)
C11	0.79695 (16)	0.9439 (3)	0.44952 (6)	0.0440 (5)
H11	0.7354	1.0111	0.4408	0.053*
C12	0.80732 (16)	0.9009 (3)	0.48974 (6)	0.0410 (5)
H12	0.7519	0.9389	0.5077	0.049*
C13	0.91900 (14)	0.7598 (3)	0.69197 (5)	0.0340 (4)
H13	0.9732	0.6703	0.6894	0.041*
C14	0.89027 (15)	0.8069 (2)	0.73343 (5)	0.0322 (4)
C15	0.96953 (15)	0.7720 (3)	0.76362 (5)	0.0366 (5)
H15	1.0367	0.7144	0.7569	0.044*
C16	0.95080 (15)	0.8209 (3)	0.80322 (6)	0.0387 (5)
H16	1.0048	0.7966	0.8228	0.046*
C17	0.85055 (15)	0.9063 (3)	0.81330 (6)	0.0381 (5)
C18	0.76801 (16)	0.9319 (3)	0.78463 (6)	0.0401 (5)
H18	0.6989	0.9821	0.7919	0.048*
C19	0.78746 (15)	0.8832 (2)	0.74526 (6)	0.0373 (5)
H19	0.7311	0.9014	0.7262	0.045*
O1	0.98058 (13)	0.6110 (2)	0.61862 (4)	0.0528 (4)
O2	0.81578 (11)	1.08088 (17)	0.61899 (4)	0.0395 (3)
O3	0.87617 (13)	0.9311 (2)	0.38255 (4)	0.0589 (4)
H3	0.8139	0.9718	0.3766	0.088*
O4	0.83014 (11)	0.9651 (2)	0.85156 (4)	0.0542 (4)
H4	0.8896	0.9992	0.8618	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0388 (10)	0.0336 (10)	0.0321 (10)	0.0021 (8)	−0.0001 (8)	−0.0024 (9)
C2	0.0376 (10)	0.0295 (10)	0.0294 (10)	−0.0016 (8)	0.0009 (8)	0.0011 (8)
C3	0.0434 (11)	0.0372 (11)	0.0316 (11)	0.0040 (8)	0.0004 (9)	0.0003 (9)
C4	0.0475 (11)	0.0368 (11)	0.0279 (10)	0.0060 (8)	0.0027 (8)	0.0010 (8)
C5	0.0360 (10)	0.0315 (10)	0.0295 (10)	−0.0003 (8)	−0.0007 (8)	−0.0016 (8)
C6	0.0369 (10)	0.0320 (10)	0.0338 (11)	0.0030 (8)	−0.0009 (8)	0.0013 (9)
C7	0.0375 (10)	0.0308 (10)	0.0299 (10)	−0.0007 (8)	0.0011 (8)	−0.0006 (8)
C8	0.0386 (11)	0.0413 (11)	0.0361 (11)	0.0057 (9)	−0.0003 (8)	−0.0013 (9)
C9	0.0412 (11)	0.0471 (12)	0.0328 (11)	0.0019 (9)	0.0066 (9)	−0.0055 (9)
C10	0.0441 (11)	0.0427 (12)	0.0317 (11)	−0.0042 (9)	−0.0012 (9)	0.0017 (9)
C11	0.0453 (12)	0.0467 (12)	0.0401 (12)	0.0122 (9)	−0.0050 (9)	0.0005 (10)
C12	0.0394 (11)	0.0494 (12)	0.0342 (11)	0.0065 (9)	0.0028 (8)	−0.0030 (9)
C13	0.0372 (10)	0.0321 (10)	0.0329 (11)	0.0014 (8)	−0.0011 (8)	−0.0041 (9)
C14	0.0378 (10)	0.0294 (10)	0.0295 (10)	−0.0004 (8)	−0.0018 (8)	−0.0016 (8)
C15	0.0356 (10)	0.0385 (11)	0.0359 (11)	0.0026 (8)	0.0006 (8)	−0.0028 (9)
C16	0.0382 (11)	0.0472 (12)	0.0307 (11)	−0.0009 (9)	−0.0059 (8)	−0.0019 (9)
C17	0.0436 (11)	0.0402 (11)	0.0306 (11)	−0.0048 (9)	0.0028 (9)	−0.0077 (9)
C18	0.0372 (11)	0.0451 (12)	0.0379 (11)	0.0022 (9)	0.0036 (9)	−0.0029 (10)
C19	0.0370 (11)	0.0412 (11)	0.0336 (11)	0.0002 (8)	−0.0038 (8)	0.0017 (9)
O1	0.0708 (10)	0.0518 (9)	0.0357 (8)	0.0293 (8)	−0.0031 (7)	−0.0019 (7)
O2	0.0563 (9)	0.0305 (7)	0.0316 (7)	0.0050 (6)	0.0022 (6)	0.0008 (6)
O3	0.0632 (10)	0.0830 (12)	0.0305 (8)	0.0091 (9)	−0.0008 (7)	0.0092 (8)
O4	0.0501 (9)	0.0778 (11)	0.0346 (8)	−0.0016 (8)	0.0036 (7)	−0.0213 (8)

Geometric parameters (Å, º) top

C1—O1	1.233 (2)	C10—O3	1.357 (2)
C1—C2	1.479 (2)	C10—C11	1.383 (3)
C1—C5	1.485 (2)	C11—C12	1.380 (3)
C2—C6	1.343 (2)	C11—H11	0.9300
C2—C3	1.503 (2)	C12—H12	0.9300
C3—O2	1.418 (2)	C13—C14	1.462 (2)
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.397 (2)
C4—O2	1.418 (2)	C14—C19	1.398 (2)
C4—C5	1.501 (3)	C15—C16	1.383 (2)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.386 (3)
C5—C13	1.340 (2)	C16—H16	0.9300
C6—C7	1.455 (2)	C17—O4	1.367 (2)
C6—H6	0.9300	C17—C18	1.376 (3)
C7—C8	1.394 (2)	C18—C19	1.377 (2)
C7—C12	1.398 (2)	C18—H18	0.9300
C8—C9	1.376 (3)	C19—H19	0.9300
C8—H8	0.9300	O3—H3	0.8200
C9—C10	1.383 (3)	O4—H4	0.8200
C9—H9	0.9300

O1—C1—C2	120.58 (16)	O3—C10—C11	123.72 (18)
O1—C1—C5	121.12 (17)	O3—C10—C9	116.96 (17)
C2—C1—C5	118.27 (16)	C11—C10—C9	119.32 (18)
C6—C2—C1	117.91 (17)	C12—C11—C10	120.24 (18)
C6—C2—C3	124.92 (16)	C12—C11—H11	119.9
C1—C2—C3	117.18 (15)	C10—C11—H11	119.9
O2—C3—C2	111.83 (14)	C11—C12—C7	121.60 (18)
O2—C3—H3A	109.2	C11—C12—H12	119.2
C2—C3—H3A	109.2	C7—C12—H12	119.2
O2—C3—H3B	109.2	C5—C13—C14	130.28 (18)
C2—C3—H3B	109.2	C5—C13—H13	114.9
H3A—C3—H3B	107.9	C14—C13—H13	114.9
O2—C4—C5	111.52 (14)	C15—C14—C19	117.14 (16)
O2—C4—H4A	109.3	C15—C14—C13	118.46 (16)
C5—C4—H4A	109.3	C19—C14—C13	124.39 (16)
O2—C4—H4B	109.3	C16—C15—C14	121.80 (17)
C5—C4—H4B	109.3	C16—C15—H15	119.1
H4A—C4—H4B	108.0	C14—C15—H15	119.1
C13—C5—C1	119.01 (17)	C15—C16—C17	119.20 (17)
C13—C5—C4	123.99 (16)	C15—C16—H16	120.4
C1—C5—C4	116.99 (15)	C17—C16—H16	120.4
C2—C6—C7	132.00 (17)	O4—C17—C18	118.33 (17)
C2—C6—H6	114.0	O4—C17—C16	121.56 (17)
C7—C6—H6	114.0	C18—C17—C16	120.10 (18)
C8—C7—C12	116.55 (17)	C17—C18—C19	120.19 (18)
C8—C7—C6	117.65 (16)	C17—C18—H18	119.9
C12—C7—C6	125.80 (16)	C19—C18—H18	119.9
C9—C8—C7	122.31 (18)	C18—C19—C14	121.31 (17)
C9—C8—H8	118.8	C18—C19—H19	119.3
C7—C8—H8	118.8	C14—C19—H19	119.3
C8—C9—C10	119.82 (17)	C3—O2—C4	111.76 (14)
C8—C9—H9	120.1	C10—O3—H3	109.5
C10—C9—H9	120.1	C17—O4—H4	109.5

O1—C1—C2—C6	−5.0 (3)	O3—C10—C11—C12	−176.96 (19)
C5—C1—C2—C6	176.83 (17)	C9—C10—C11—C12	2.8 (3)
O1—C1—C2—C3	175.61 (18)	C10—C11—C12—C7	0.6 (3)
C5—C1—C2—C3	−2.6 (2)	C8—C7—C12—C11	−3.3 (3)
C6—C2—C3—O2	−148.76 (18)	C6—C7—C12—C11	176.68 (19)
C1—C2—C3—O2	30.6 (2)	C1—C5—C13—C14	−176.43 (17)
O1—C1—C5—C13	5.4 (3)	C4—C5—C13—C14	3.7 (3)
C2—C1—C5—C13	−176.41 (16)	C5—C13—C14—C15	−156.10 (19)
O1—C1—C5—C4	−174.69 (18)	C5—C13—C14—C19	24.7 (3)
C2—C1—C5—C4	3.5 (2)	C19—C14—C15—C16	−4.0 (3)
O2—C4—C5—C13	147.53 (18)	C13—C14—C15—C16	176.72 (18)
O2—C4—C5—C1	−32.3 (2)	C14—C15—C16—C17	0.2 (3)
C1—C2—C6—C7	178.79 (18)	C15—C16—C17—O4	−176.80 (18)
C3—C2—C6—C7	−1.9 (3)	C15—C16—C17—C18	4.0 (3)
C2—C6—C7—C8	162.9 (2)	O4—C17—C18—C19	176.59 (18)
C2—C6—C7—C12	−17.0 (3)	C16—C17—C18—C19	−4.2 (3)
C12—C7—C8—C9	2.8 (3)	C17—C18—C19—C14	0.2 (3)
C6—C7—C8—C9	−177.20 (17)	C15—C14—C19—C18	3.9 (3)
C7—C8—C9—C10	0.5 (3)	C13—C14—C19—C18	−176.94 (18)
C8—C9—C10—O3	176.46 (18)	C2—C3—O2—C4	−62.06 (19)
C8—C9—C10—C11	−3.4 (3)	C5—C4—O2—C3	62.96 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.95	2.757 (2)	167
O4—H4···O1ⁱⁱ	0.82	1.86	2.677 (2)	171

Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₄
M_r	308.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	11.812 (3), 7.4687 (16), 33.233 (7)
V (Å³)	2931.9 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.37 × 0.29

Data collection
Diffractometer	Bruker SMART CCD 1K area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	16659, 3224, 1941
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.04
No. of reflections	3224
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.95	2.757 (2)	167
O4—H4···O1ⁱⁱ	0.82	1.86	2.677 (2)	171

Symmetry codes: (i) −x+3/2, −y+2, z−1/2; (ii) −x+2, y+1/2, −z+3/2.

Acknowledgements

We thank the projects of China National Natural Science Funds, Guangdong Provincial Science Foundation and the 211 project of Guangdong Province for support.

References

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