2-(2-Hydroxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium acetate monohydrate

Wen, H.-L.; He, M.; Liu, C.-B.

doi:10.1107/S1600536808028626

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1949

doi:10.1107/S1600536808028626

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2-(2-Hydroxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium acetate monohydrate

Hui-Liang Wen,^a,^b ^* Min He ^a and Chong-Bo Liu ^c

^aDepartment of Chemistry, Nanchang University, Nanchang 330031, People's Republic of China, ^bState Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, People's Republic of China, and ^cCollege of Environmental and Chemical Engineering, Nanchang University of Aeronautics, Nanchang 330063, People's Republic of China
^*Correspondence e-mail: hlwen70@163.com

(Received 16 August 2008; accepted 7 September 2008; online 17 September 2008)

In the title compound, C₁₁H₁₃N₂O⁺·C₂H₃O₂⁻·H₂O, the dihedral angle between the benzene ring and the imidazole ring is 7.83 (6)°. In the crystal structure, N—H⋯O and O—H⋯O hydrogen bonds form a two-dimensional network. All the methyl H atoms are disorderd over two sites with equal occupancies.

Related literature

For related literature, see: Maeda et al. (1984 ); Puratchikody & Doble (2007 ); Quattara et al. (1987 ); Ucucu et al. (2001 ); Scott et al. (2004 ); Seko et al. (1991 ).

Experimental

Crystal data

C₁₁H₁₃N₂O⁺·C₂H₃O₂⁻·H₂O
M_r = 266.29
Monoclinic, P 2₁ /n
a = 8.1655 (12) Å
b = 9.6542 (14) Å
c = 17.141 (3) Å
β = 96.374 (2)°
V = 1342.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 (2) K
0.46 × 0.38 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.977
8442 measured reflections
2488 independent reflections
1751 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.05
2488 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2D⋯O4	0.86	1.93	2.7747 (19)	169
N1—H1D⋯O1	0.86	2.17	2.6956 (19)	119
N1—H1D⋯O3	0.86	2.10	2.834 (2)	142
O4—H2W⋯O3ⁱ	0.84	1.89	2.710 (2)	164
O4—H1W⋯O2ⁱⁱ	0.84	2.07	2.808 (2)	146
O1—H1⋯O2ⁱⁱⁱ	0.82	1.76	2.5624 (18)	167
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028626/lh2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028626/lh2684Isup2.hkl

checkCIF report

Comment top

Imidazole derivatives can have a wide range of biological activities such as analgesic (Ucucu et al., 2001), antiinflammmatory (Maeda et al., 1984), antiparasitic (Quattara et al., 1987), antiepileptic and platelet aggregation inhibitors (Seko et al., 1991). The neutral imidizole component of the title compound could potentially exhibit biological activities (Puratchikody & Doble, 2007). In this paper, we report the crystal structure of the title compound (I).

In the title compound (Fig. 1), the benzene ring and the imidazole ring are approximately co-planar with a dihedral angle of 7.83 (6)° between them. The components of the salt are linked via N-H···O hydrogen bonds. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds link the components of the title compound into a two-dimensional network.

Related literature top

For related literature, see: Maeda et al. (1984); Puratchikody & Doble (2007); Quattara et al. (1987); Ucucu et al. (2001); Scott et al. (2004); Seko et al. (1991).

Experimental top

The title compound was prepared according to a literature method (Scott et al., 2004). 1.72 g (20 mmol) butane-2,3-dione, 2.44 g (20 mmol), 4-hydroxybenzaldehyde and 5 g (>50 mmol) NH₄Ac were placed in a sealed container with 100 ml CH₃Cl:HAc (4:1) as the solvent and heated in a micro-wave at 350 W for 24 min. After the reaction, the solvent was evaporated. The pure product as a dark red crystalline solid was obtained by re-crystallization from hot EtOH/H₂O in a yield of 81.6% and suitable for X-ray diffraction analysis.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. : The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as spheres of arbitrary radii. Hydrogen bonds are shown as a dashed lines. Only one disorder site for each methyl H atom is showm.
	Fig. 2. : Part of the crystal structure with hydrogen bonds shown as dashed lines.

2-(2-Hydroxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium acetate monohydrate top

Crystal data top

C₁₁H₁₃N₂O⁺·C₂H₃O₂⁻·H₂O	F(000) = 568
M_r = 266.29	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1719 reflections
a = 8.1655 (12) Å	θ = 2.4–21.9°
b = 9.6542 (14) Å	µ = 0.10 mm⁻¹
c = 17.141 (3) Å	T = 295 K
β = 96.374 (2)°	Block, yellow
V = 1342.9 (3) Å³	0.46 × 0.38 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1751 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.956, T_max = 0.977	k = −11→11
8442 measured reflections	l = −20→20

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0429P)² + 0.2995P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2488 reflections	Δρ_max = 0.20 e Å⁻³
174 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (16)

Crystal data top

C₁₁H₁₃N₂O⁺·C₂H₃O₂⁻·H₂O	V = 1342.9 (3) Å³
M_r = 266.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1655 (12) Å	µ = 0.10 mm⁻¹
b = 9.6542 (14) Å	T = 295 K
c = 17.141 (3) Å	0.46 × 0.38 × 0.24 mm
β = 96.374 (2)°

Data collection top

Bruker SMART CCD diffractometer	2488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1751 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.977	R_int = 0.032
8442 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
2488 reflections	Δρ_min = −0.15 e Å⁻³
174 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	Occ. (<1)
O1	0.43862 (18)	0.76646 (13)	−0.03904 (8)	0.0587 (4)
H1	0.5030	0.7086	−0.0529	0.088*
O3	0.24781 (18)	0.61838 (14)	0.08451 (11)	0.0777 (5)
O2	0.33771 (17)	0.41072 (13)	0.06150 (9)	0.0600 (4)
O4	0.08440 (17)	1.35614 (13)	−0.05919 (8)	0.0593 (4)
H1W	0.1378	1.4036	−0.0243	0.089*
H2W	−0.0162	1.3770	−0.0610	0.089*
N1	0.25223 (18)	0.90693 (15)	0.05447 (9)	0.0435 (4)
H1D	0.2938	0.8251	0.0545	0.052*
N2	0.17344 (18)	1.11013 (14)	0.01783 (9)	0.0411 (4)
H2D	0.1545	1.1834	−0.0103	0.049*
C1	0.4058 (2)	0.86127 (18)	−0.09630 (11)	0.0425 (4)
C2	0.3119 (2)	0.97773 (17)	−0.08056 (10)	0.0385 (4)
C3	0.2787 (2)	1.07700 (19)	−0.13939 (11)	0.0467 (5)
H3	0.2185	1.1555	−0.1293	0.056*
C4	0.3333 (3)	1.0612 (2)	−0.21208 (12)	0.0546 (5)
H4	0.3099	1.1282	−0.2507	0.066*
C5	0.4233 (3)	0.9446 (2)	−0.22712 (12)	0.0562 (6)
H5	0.4589	0.9326	−0.2764	0.067*
C6	0.4602 (2)	0.8466 (2)	−0.17006 (12)	0.0521 (5)
H6	0.5223	0.7695	−0.1807	0.063*
C7	0.2492 (2)	0.99653 (17)	−0.00505 (10)	0.0388 (4)
C8	0.1793 (2)	0.96438 (19)	0.11599 (11)	0.0444 (5)
C9	0.1301 (2)	1.09338 (18)	0.09268 (11)	0.0429 (5)
C10	0.1708 (3)	0.8898 (2)	0.19128 (12)	0.0630 (6)
H10A	0.2175	0.7991	0.1880	0.095*	0.50
H10B	0.0578	0.8818	0.2013	0.095*	0.50
H10C	0.2314	0.9405	0.2332	0.095*	0.50
H10D	0.1203	0.9485	0.2270	0.095*	0.50
H10E	0.2800	0.8658	0.2137	0.095*	0.50
H10F	0.1064	0.8071	0.1818	0.095*	0.50
C11	0.0489 (3)	1.2060 (2)	0.13390 (12)	0.0574 (6)
H11A	0.0308	1.2846	0.0997	0.086*	0.50
H11B	0.1186	1.2325	0.1803	0.086*	0.50
H11C	−0.0547	1.1735	0.1482	0.086*	0.50
H11D	0.0323	1.1758	0.1858	0.086*	0.50
H11E	−0.0555	1.2279	0.1052	0.086*	0.50
H11F	0.1178	1.2869	0.1373	0.086*	0.50
C12	0.3592 (2)	0.53088 (18)	0.08843 (11)	0.0448 (5)
C13	0.5261 (3)	0.5695 (2)	0.12663 (14)	0.0641 (6)
H13F	0.6052	0.5599	0.0895	0.096*	0.50
H13E	0.5559	0.5097	0.1707	0.096*	0.50
H13D	0.5248	0.6638	0.1443	0.096*	0.50
H13C	0.5187	0.5957	0.1802	0.096*	0.50
H13B	0.5680	0.6459	0.0990	0.096*	0.50
H13A	0.5991	0.4918	0.1253	0.096*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0687 (10)	0.0470 (8)	0.0630 (9)	0.0195 (7)	0.0194 (8)	0.0032 (7)
O3	0.0517 (9)	0.0506 (9)	0.1328 (15)	0.0125 (7)	0.0196 (10)	0.0043 (9)
O2	0.0515 (9)	0.0434 (8)	0.0842 (11)	0.0017 (6)	0.0039 (7)	−0.0110 (7)
O4	0.0526 (8)	0.0550 (8)	0.0698 (10)	0.0083 (7)	0.0045 (7)	−0.0070 (7)
N1	0.0426 (9)	0.0386 (8)	0.0498 (10)	0.0050 (7)	0.0073 (7)	0.0003 (7)
N2	0.0427 (9)	0.0363 (8)	0.0449 (9)	0.0021 (7)	0.0073 (7)	−0.0021 (7)
C1	0.0399 (10)	0.0394 (10)	0.0482 (11)	−0.0008 (8)	0.0054 (9)	−0.0036 (8)
C2	0.0358 (10)	0.0358 (9)	0.0443 (11)	−0.0021 (7)	0.0061 (8)	−0.0057 (8)
C3	0.0444 (11)	0.0444 (11)	0.0513 (12)	0.0015 (8)	0.0054 (9)	−0.0031 (9)
C4	0.0615 (13)	0.0566 (12)	0.0460 (12)	−0.0016 (10)	0.0074 (10)	0.0015 (9)
C5	0.0599 (13)	0.0641 (13)	0.0463 (12)	−0.0030 (11)	0.0128 (10)	−0.0110 (10)
C6	0.0529 (12)	0.0492 (11)	0.0558 (13)	0.0038 (9)	0.0130 (10)	−0.0116 (10)
C7	0.0350 (10)	0.0362 (9)	0.0451 (11)	0.0007 (7)	0.0044 (8)	−0.0042 (8)
C8	0.0411 (11)	0.0474 (11)	0.0455 (11)	−0.0026 (8)	0.0078 (9)	−0.0026 (9)
C9	0.0387 (10)	0.0456 (11)	0.0452 (11)	−0.0028 (8)	0.0080 (8)	−0.0074 (8)
C10	0.0687 (15)	0.0692 (14)	0.0525 (13)	0.0011 (11)	0.0132 (11)	0.0092 (10)
C11	0.0586 (13)	0.0541 (12)	0.0624 (13)	−0.0034 (10)	0.0197 (11)	−0.0159 (10)
C12	0.0430 (11)	0.0398 (11)	0.0532 (12)	0.0012 (9)	0.0117 (9)	0.0049 (9)
C13	0.0551 (14)	0.0678 (14)	0.0682 (15)	−0.0103 (11)	0.0010 (11)	−0.0017 (12)

Geometric parameters (Å, º) top

O1—C1	1.347 (2)	C8—C9	1.355 (2)
O1—H1	0.8200	C8—C10	1.486 (3)
O3—C12	1.238 (2)	C9—C11	1.492 (2)
O2—C12	1.254 (2)	C10—H10A	0.9600
O4—H1W	0.8364	C10—H10B	0.9600
O4—H2W	0.8428	C10—H10C	0.9600
N1—C7	1.336 (2)	C10—H10D	0.9600
N1—C8	1.383 (2)	C10—H10E	0.9600
N1—H1D	0.8600	C10—H10F	0.9600
N2—C7	1.339 (2)	C11—H11A	0.9600
N2—C9	1.378 (2)	C11—H11B	0.9600
N2—H2D	0.8600	C11—H11C	0.9600
C1—C6	1.393 (3)	C11—H11D	0.9600
C1—C2	1.404 (2)	C11—H11E	0.9600
C2—C3	1.396 (2)	C11—H11F	0.9600
C2—C7	1.455 (2)	C12—C13	1.493 (3)
C3—C4	1.377 (3)	C13—H13F	0.9600
C3—H3	0.9300	C13—H13E	0.9600
C4—C5	1.384 (3)	C13—H13D	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.370 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13A	0.9600
C6—H6	0.9300

C1—O1—H1	109.5	H10A—C10—H10F	56.3
H1W—O4—H2W	108.9	H10B—C10—H10F	56.3
C7—N1—C8	110.46 (14)	H10C—C10—H10F	141.1
C7—N1—H1D	124.7	H10D—C10—H10F	109.5
C8—N1—H1D	124.8	H10E—C10—H10F	109.5
C7—N2—C9	110.57 (14)	C9—C11—H11A	109.5
C7—N2—H2D	124.7	C9—C11—H11B	109.5
C9—N2—H2D	124.7	H11A—C11—H11B	109.5
O1—C1—C6	122.33 (16)	C9—C11—H11C	109.5
O1—C1—C2	118.22 (16)	H11A—C11—H11C	109.5
C6—C1—C2	119.44 (17)	H11B—C11—H11C	109.5
C3—C2—C1	118.52 (16)	C9—C11—H11D	109.5
C3—C2—C7	119.85 (15)	H11A—C11—H11D	141.1
C1—C2—C7	121.63 (16)	H11B—C11—H11D	56.3
C4—C3—C2	121.41 (18)	H11C—C11—H11D	56.3
C4—C3—H3	119.3	C9—C11—H11E	109.5
C2—C3—H3	119.3	H11A—C11—H11E	56.3
C3—C4—C5	119.36 (19)	H11B—C11—H11E	141.1
C3—C4—H4	120.3	H11C—C11—H11E	56.3
C5—C4—H4	120.3	H11D—C11—H11E	109.5
C6—C5—C4	120.52 (18)	C9—C11—H11F	109.5
C6—C5—H5	119.7	H11A—C11—H11F	56.3
C4—C5—H5	119.7	H11B—C11—H11F	56.3
C5—C6—C1	120.73 (18)	H11C—C11—H11F	141.1
C5—C6—H6	119.6	H11D—C11—H11F	109.5
C1—C6—H6	119.6	H11E—C11—H11F	109.5
N1—C7—N2	106.06 (15)	O3—C12—O2	122.65 (19)
N1—C7—C2	128.32 (15)	O3—C12—C13	118.89 (18)
N2—C7—C2	125.61 (16)	O2—C12—C13	118.46 (17)
C9—C8—N1	106.41 (15)	C12—C13—H13F	109.5
C9—C8—C10	131.30 (17)	C12—C13—H13E	109.5
N1—C8—C10	122.25 (16)	H13F—C13—H13E	109.5
C8—C9—N2	106.49 (15)	C12—C13—H13D	109.5
C8—C9—C11	131.55 (17)	H13F—C13—H13D	109.5
N2—C9—C11	121.95 (17)	H13E—C13—H13D	109.5
C8—C10—H10A	109.5	C12—C13—H13C	109.5
C8—C10—H10B	109.5	H13F—C13—H13C	141.1
H10A—C10—H10B	109.5	H13E—C13—H13C	56.3
C8—C10—H10C	109.5	H13D—C13—H13C	56.3
H10A—C10—H10C	109.5	C12—C13—H13B	109.5
H10B—C10—H10C	109.5	H13F—C13—H13B	56.3
C8—C10—H10D	109.5	H13E—C13—H13B	141.1
H10A—C10—H10D	141.1	H13D—C13—H13B	56.3
H10B—C10—H10D	56.3	H13C—C13—H13B	109.5
H10C—C10—H10D	56.3	C12—C13—H13A	109.5
C8—C10—H10E	109.5	H13F—C13—H13A	56.3
H10A—C10—H10E	56.3	H13E—C13—H13A	56.3
H10B—C10—H10E	141.1	H13D—C13—H13A	141.1
H10C—C10—H10E	56.3	H13C—C13—H13A	109.5
H10D—C10—H10E	109.5	H13B—C13—H13A	109.5
C8—C10—H10F	109.5

O1—C1—C2—C3	179.44 (16)	C9—N2—C7—C2	−179.93 (16)
C6—C1—C2—C3	−1.2 (3)	C3—C2—C7—N1	171.82 (17)
O1—C1—C2—C7	−0.6 (3)	C1—C2—C7—N1	−8.1 (3)
C6—C1—C2—C7	178.69 (16)	C3—C2—C7—N2	−7.3 (3)
C1—C2—C3—C4	1.3 (3)	C1—C2—C7—N2	172.81 (16)
C7—C2—C3—C4	−178.65 (17)	C7—N1—C8—C9	0.1 (2)
C2—C3—C4—C5	−0.2 (3)	C7—N1—C8—C10	−177.72 (17)
C3—C4—C5—C6	−1.0 (3)	N1—C8—C9—N2	0.34 (19)
C4—C5—C6—C1	1.1 (3)	C10—C8—C9—N2	177.9 (2)
O1—C1—C6—C5	179.40 (18)	N1—C8—C9—C11	−178.04 (19)
C2—C1—C6—C5	0.1 (3)	C10—C8—C9—C11	−0.4 (4)
C8—N1—C7—N2	−0.59 (19)	C7—N2—C9—C8	−0.7 (2)
C8—N1—C7—C2	−179.82 (17)	C7—N2—C9—C11	177.84 (17)
C9—N2—C7—N1	0.82 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2D···O4	0.86	1.93	2.7747 (19)	169
N1—H1D···O1	0.86	2.17	2.6956 (19)	119
N1—H1D···O3	0.86	2.10	2.834 (2)	142
O4—H2W···O3ⁱ	0.84	1.89	2.710 (2)	164
O4—H1W···O2ⁱⁱ	0.84	2.07	2.808 (2)	146
O1—H1···O2ⁱⁱⁱ	0.82	1.76	2.5624 (18)	167

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₂O⁺·C₂H₃O₂⁻·H₂O
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	8.1655 (12), 9.6542 (14), 17.141 (3)
β (°)	96.374 (2)
V (Å³)	1342.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.46 × 0.38 × 0.24

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	8442, 2488, 1751
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.05
No. of reflections	2488
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
N2—H2D···O4	0.86	1.93	2.7747 (19)	169.3
N1—H1D···O1	0.86	2.17	2.6956 (19)	119.1
N1—H1D···O3	0.86	2.10	2.834 (2)	142.3
O4—H2W···O3ⁱ	0.84	1.89	2.710 (2)	164.0
O4—H1W···O2ⁱⁱ	0.84	2.07	2.808 (2)	146.3
O1—H1···O2ⁱⁱⁱ	0.82	1.76	2.5624 (18)	167.4

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

Acknowledgements

This work is supported by the National Natural Science Foundation of China (20662007) and the Key Laboratory Open Foundation of Food Science of the Ministry of Education, Nanchang University (NCU200407).

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