9-[4-Hydr­oxy-3-(hydroxy­meth­yl)but­yl]guanine monohydrate

Tang, H.; Cheng, F.-J.; Li, N.; Liu, Y.-C.; Chen, Z.-F.

doi:10.1107/S1600536809043980

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2878

https://doi.org/10.1107/S1600536809043980

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9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine monohydrate

Huang Tang,^a Feng-Jie Cheng,^a Nan Li,^a Yan-Cheng Liu ^a and Zhen-Feng Chen ^a ^*

^aKey Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education), School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: chenzfgxnu@yahoo.com

(Received 1 September 2009; accepted 23 October 2009; online 28 October 2009)

In the molecular structure of the title compound, also named penciclovir monohydrate, C₁₀H₁₅N₅O₃·H₂O, the 4-hydroxy-3-hydroxymethylbut-1-yl group is connected to guanine through an N atom of the imidazole ring. Water molecules stabilize the molecular packing by forming O—H⋯O hydrogen bonds. A three-dimensional network is generated via intermolecular N—H⋯N, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonding.

Related literature

For the synthesis and biological properies of penciclovir, see: Harnden & Jarvest (1985a ,b ); Hodge et al.(1989 ); Boyd et al. (1987 ). For the medicinal applications of penciclovir, see: Abdel-Hag et al. (2006 ); Andrei et al. (2004 ); Schmid-Wendtner & Korting (2004 ); Smith et al. (2001 ).

Experimental

Crystal data

C₁₀H₁₅N₅O₃·H₂O
M_r = 271.29
Orthorhombic, P n a 2₁
a = 8.2020 (16) Å
b = 13.889 (3) Å
c = 11.001 (2) Å
V = 1253.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.54 × 0.45 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.957, T_max = 0.994
6830 measured reflections
1193 independent reflections
1084 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.118
S = 1.06
1193 reflections
186 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4ⁱ	0.82	1.90	2.719 (3)	175
O3—H3A⋯N3ⁱⁱ	0.82	2.24	3.052 (3)	169
N4—H4⋯N2ⁱⁱⁱ	0.96 (3)	1.86 (3)	2.816 (3)	176 (3)
O4—H4A⋯O2^iv	0.86 (3)	1.93 (3)	2.787 (3)	178 (3)
O4—H4B⋯O1^v	0.84 (3)	2.11 (5)	2.842 (3)	146 (3)
N5—H5A⋯O2ⁱ	0.86	2.15	2.898 (3)	146
N5—H5B⋯O1ⁱⁱⁱ	0.86	2.11	2.931 (3)	159
Symmetry codes: (i) $[-x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x, -y, z+{\script{1\over 2}}]$ ; (iii) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); 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 I, global. DOI: https://doi.org/10.1107/S1600536809043980/ds2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043980/ds2005Isup2.hkl

checkCIF report

Comment top

9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine (I), known as penciclovir, is very effective for the treatment of herpes simplex virus, varicella zoster virus, Epstein–Barr virus, hepatitis virus and cytomegalovirus (Abdel-Hag et al., 2006; Andrei et al., 2004; Schmid-Wendtner and Korting, 2004; Smith et al., 2001). The crystal lattice is built from molecules of (I) and waters of crystallization (Fig. 1). The guanine ring in (I) is coplanar wherein the C—N bond distances range from 1.312 (4) to 1.395 (5) Å. Three dimensional network is generated via N—H···N, N—H···O (2.816 (3)–2.931 (3) Å,), O—H···N(3.052 (3) Å), and O—H···O(2.719 (3)–2.842 (3) Å) hydrogen bonds from water and penciclovir molecules (Fig.2).

Related literature top

For the synthesis and biological properies of penciclovir, see: Harnden & Jarvest (1985a,b); Hodge et al.(1989); Boyd et al. (1987). For the medicinal applications of penciclovir, see: Abdel-Hag et al. (2006); Andrei et al. (2004); Schmid-Wendtner & Korting (2004); Smith et al. (2001). AUTHORS: Provide figure captions (including probability level for ellipsoid plot).

Experimental top

0.2 mmol ZnCl₂ dissolved in 5 ml ethanol was added into 10 ml water containing 0.3 mmol pencicolvir. The mixture was stirred at room temperature for 5 h. The resulting solution was filtered. The filtrate was allowed to stay at ambient temperature for three weeks. Colourless block crystals were thus obtained. Yeild: 50%.

Structure description top

For the synthesis and biological properies of penciclovir, see: Harnden & Jarvest (1985a,b); Hodge et al.(1989); Boyd et al. (1987). For the medicinal applications of penciclovir, see: Abdel-Hag et al. (2006); Andrei et al. (2004); Schmid-Wendtner & Korting (2004); Smith et al. (2001). AUTHORS: Provide figure captions (including probability level for ellipsoid plot).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (I),showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Three-dimensional structure of (I) along [001] direction. Hydrogen bonds are shown as dashed lines.

9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine monohydrate top

Crystal data top

C₁₀H₁₅N₅O₃·H₂O	F(000) = 576
M_r = 271.29	D_x = 1.438 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1193 reflections
a = 8.2020 (16) Å	θ = 3.4–25.2°
b = 13.889 (3) Å	µ = 0.11 mm⁻¹
c = 11.001 (2) Å	T = 293 K
V = 1253.2 (4) Å³	Block, colorless
Z = 4	0.54 × 0.45 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1193 independent reflections
Radiation source: fine-focus sealed tube	1084 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 25.2°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −8→9
T_min = 0.957, T_max = 0.994	k = −16→16
6830 measured reflections	l = −11→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0604P)² + 0.3P] where P = (F_o² + 2F_c²)/3
1193 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 0.15 e Å⁻³
4 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₀H₁₅N₅O₃·H₂O	V = 1253.2 (4) Å³
M_r = 271.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.2020 (16) Å	µ = 0.11 mm⁻¹
b = 13.889 (3) Å	T = 293 K
c = 11.001 (2) Å	0.54 × 0.45 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1193 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1084 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.994	R_int = 0.075
6830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	4 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.15 e Å⁻³
1193 reflections	Δρ_min = −0.31 e Å⁻³
186 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
C1	0.0269 (5)	0.4750 (3)	0.0559 (4)	0.0321 (9)
C2	−0.0398 (5)	0.3455 (3)	−0.0873 (4)	0.0354 (9)
C3	−0.0027 (5)	0.3211 (3)	0.3070 (4)	0.0374 (10)
H3	−0.0018	0.3037	0.3886	0.045*
C4	−0.0242 (5)	0.3102 (2)	0.1084 (4)	0.0311 (9)
C5	0.0189 (5)	−0.0152 (3)	0.2010 (4)	0.0375 (9)
H5	−0.0741	−0.0176	0.1452	0.045*
C6	0.0126 (5)	0.4027 (3)	0.1448 (4)	0.0323 (9)
C7	−0.0735 (5)	0.1556 (3)	0.2279 (4)	0.0396 (10)
H7A	−0.1567	0.1390	0.1689	0.048*
H7B	−0.1185	0.1448	0.3083	0.048*
C8	0.0713 (5)	0.0901 (3)	0.2102 (5)	0.0383 (9)
H8A	0.1458	0.0977	0.2780	0.046*
H8B	0.1286	0.1084	0.1366	0.046*
C9	−0.0360 (6)	−0.0601 (3)	0.3195 (5)	0.0537 (13)
H9A	−0.1190	−0.0197	0.3563	0.064*
H9B	−0.0841	−0.1226	0.3032	0.064*
C10	0.1551 (5)	−0.0729 (3)	0.1431 (4)	0.0424 (11)
H10A	0.1837	−0.0435	0.0660	0.051*
H10B	0.2504	−0.0699	0.1952	0.051*
N1	−0.0334 (4)	0.2576 (2)	0.2150 (3)	0.0352 (8)
N2	0.0253 (4)	0.4092 (2)	0.2691 (3)	0.0356 (8)
N3	−0.0498 (4)	0.2759 (2)	−0.0038 (3)	0.0354 (8)
N4	−0.0054 (4)	0.4399 (2)	−0.0607 (4)	0.0359 (8)
N5	−0.0645 (5)	0.3259 (3)	−0.2040 (4)	0.0506 (10)
H5A	−0.0871	0.2680	−0.2263	0.061*
H5B	−0.0579	0.3710	−0.2573	0.061*
O1	0.0604 (4)	0.56135 (18)	0.0709 (3)	0.0396 (7)
O2	0.1144 (4)	−0.17160 (18)	0.1226 (3)	0.0485 (8)
H2	0.0219	−0.1752	0.0948	0.073*
O3	0.0950 (6)	−0.0711 (3)	0.4012 (4)	0.0760 (12)
H3A	0.0878	−0.1234	0.4354	0.114*
O4	0.1827 (4)	0.1915 (2)	0.5157 (4)	0.0518 (8)
H4	−0.017 (7)	0.489 (4)	−0.119 (6)	0.068 (17)*
H4A	0.243 (6)	0.234 (3)	0.549 (5)	0.069 (17)*
H4B	0.222 (9)	0.1362 (19)	0.527 (8)	0.14 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.029 (2)	0.031 (2)	−0.0005 (16)	−0.0003 (17)	−0.0003 (17)
C2	0.045 (2)	0.031 (2)	0.031 (2)	0.0021 (16)	0.0000 (18)	−0.0032 (19)
C3	0.050 (2)	0.032 (2)	0.030 (2)	0.0036 (17)	0.0007 (19)	0.0023 (18)
C4	0.040 (2)	0.0252 (18)	0.028 (2)	0.0044 (15)	−0.0008 (18)	−0.0019 (17)
C5	0.043 (2)	0.031 (2)	0.039 (3)	−0.0014 (16)	0.000 (2)	0.003 (2)
C6	0.041 (2)	0.0264 (18)	0.029 (2)	0.0027 (15)	−0.0015 (17)	−0.0031 (17)
C7	0.051 (2)	0.0270 (19)	0.041 (3)	−0.0016 (17)	0.0036 (19)	0.0063 (19)
C8	0.041 (2)	0.0288 (19)	0.045 (3)	−0.0016 (16)	−0.003 (2)	0.0041 (19)
C9	0.059 (3)	0.042 (3)	0.060 (4)	−0.004 (2)	0.014 (3)	0.006 (2)
C10	0.050 (2)	0.033 (2)	0.045 (3)	−0.0005 (17)	0.008 (2)	0.0043 (19)
N1	0.053 (2)	0.0217 (14)	0.031 (2)	0.0013 (13)	0.0017 (18)	0.0038 (15)
N2	0.0508 (19)	0.0308 (16)	0.025 (2)	0.0009 (15)	0.0000 (16)	−0.0018 (15)
N3	0.0492 (19)	0.0296 (17)	0.028 (2)	−0.0021 (15)	0.0012 (15)	−0.0013 (15)
N4	0.053 (2)	0.0274 (17)	0.028 (2)	−0.0031 (14)	0.0004 (16)	0.0017 (15)
N5	0.088 (3)	0.0347 (18)	0.029 (2)	−0.0071 (18)	−0.005 (2)	−0.0013 (16)
O1	0.0618 (18)	0.0260 (13)	0.0311 (18)	−0.0097 (13)	0.0054 (13)	−0.0011 (12)
O2	0.0553 (17)	0.0275 (13)	0.063 (2)	0.0027 (12)	0.0003 (17)	−0.0004 (15)
O3	0.109 (3)	0.066 (2)	0.053 (3)	−0.018 (2)	−0.018 (2)	0.0180 (19)
O4	0.0547 (18)	0.0418 (17)	0.059 (2)	0.0001 (16)	−0.0074 (17)	0.0026 (16)

Geometric parameters (Å, º) top

C1—O1	1.241 (5)	C7—C8	1.508 (6)
C1—N4	1.397 (6)	C7—H7A	0.9700
C1—C6	1.407 (6)	C7—H7B	0.9700
C2—N5	1.329 (6)	C8—H8A	0.9700
C2—N3	1.336 (5)	C8—H8B	0.9700
C2—N4	1.372 (5)	C9—O3	1.410 (6)
C3—N2	1.312 (5)	C9—H9A	0.9700
C3—N1	1.366 (6)	C9—H9B	0.9700
C3—H3	0.9300	C10—O2	1.429 (5)
C4—N3	1.340 (5)	C10—H10A	0.9700
C4—C6	1.379 (5)	C10—H10B	0.9700
C4—N1	1.383 (5)	N4—H4	0.94 (6)
C5—C9	1.514 (7)	N5—H5A	0.8600
C5—C10	1.515 (6)	N5—H5B	0.8600
C5—C8	1.528 (5)	O2—H2	0.8200
C5—H5	0.9800	O3—H3A	0.8200
C6—N2	1.375 (5)	O4—H4A	0.85 (5)
C7—N1	1.461 (5)	O4—H4B	0.84 (2)

O1—C1—N4	120.1 (4)	C7—C8—H8B	109.3
O1—C1—C6	128.0 (4)	C5—C8—H8B	109.3
N4—C1—C6	111.9 (3)	H8A—C8—H8B	108.0
N5—C2—N3	120.4 (4)	O3—C9—C5	111.5 (4)
N5—C2—N4	115.7 (4)	O3—C9—H9A	109.3
N3—C2—N4	123.9 (4)	C5—C9—H9A	109.3
N2—C3—N1	113.5 (4)	O3—C9—H9B	109.3
N2—C3—H3	123.2	C5—C9—H9B	109.3
N1—C3—H3	123.2	H9A—C9—H9B	108.0
N3—C4—C6	129.3 (4)	O2—C10—C5	113.7 (3)
N3—C4—N1	125.8 (3)	O2—C10—H10A	108.8
C6—C4—N1	104.9 (4)	C5—C10—H10A	108.8
C9—C5—C10	111.3 (3)	O2—C10—H10B	108.8
C9—C5—C8	114.9 (4)	C5—C10—H10B	108.8
C10—C5—C8	109.1 (3)	H10A—C10—H10B	107.7
C9—C5—H5	107.0	C3—N1—C4	106.1 (3)
C10—C5—H5	107.0	C3—N1—C7	126.6 (4)
C8—C5—H5	107.0	C4—N1—C7	127.3 (4)
N2—C6—C4	111.5 (4)	C3—N2—C6	104.0 (4)
N2—C6—C1	129.7 (4)	C2—N3—C4	111.5 (3)
C4—C6—C1	118.8 (4)	C2—N4—C1	124.6 (4)
N1—C7—C8	113.3 (3)	C2—N4—H4	122 (4)
N1—C7—H7A	108.9	C1—N4—H4	113 (4)
C8—C7—H7A	108.9	C2—N5—H5A	120.0
N1—C7—H7B	108.9	C2—N5—H5B	120.0
C8—C7—H7B	108.9	H5A—N5—H5B	120.0
H7A—C7—H7B	107.7	C10—O2—H2	109.5
C7—C8—C5	111.4 (3)	C9—O3—H3A	109.5
C7—C8—H8A	109.3	H4A—O4—H4B	110 (3)
C5—C8—H8A	109.3

N3—C4—C6—N2	178.4 (4)	N3—C4—N1—C3	−178.5 (4)
N1—C4—C6—N2	−0.4 (4)	C6—C4—N1—C3	0.3 (4)
N3—C4—C6—C1	0.1 (6)	N3—C4—N1—C7	−0.5 (6)
N1—C4—C6—C1	−178.6 (3)	C6—C4—N1—C7	178.3 (3)
O1—C1—C6—N2	2.8 (7)	C8—C7—N1—C3	−98.2 (5)
N4—C1—C6—N2	−175.9 (4)	C8—C7—N1—C4	84.2 (5)
O1—C1—C6—C4	−179.3 (4)	N1—C3—N2—C6	−0.2 (5)
N4—C1—C6—C4	2.0 (5)	C4—C6—N2—C3	0.3 (5)
N1—C7—C8—C5	−169.4 (4)	C1—C6—N2—C3	178.4 (4)
C9—C5—C8—C7	−72.7 (5)	N5—C2—N3—C4	−178.8 (4)
C10—C5—C8—C7	161.5 (4)	N4—C2—N3—C4	0.8 (5)
C10—C5—C9—O3	56.0 (5)	C6—C4—N3—C2	−1.6 (6)
C8—C5—C9—O3	−68.6 (5)	N1—C4—N3—C2	176.9 (4)
C9—C5—C10—O2	56.1 (5)	N5—C2—N4—C1	−178.9 (4)
C8—C5—C10—O2	−176.0 (4)	N3—C2—N4—C1	1.4 (6)
N2—C3—N1—C4	−0.1 (4)	O1—C1—N4—C2	178.4 (4)
N2—C3—N1—C7	−178.1 (3)	C6—C1—N4—C2	−2.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱ	0.82	1.90	2.719 (3)	175
O3—H3A···N3ⁱⁱ	0.82	2.24	3.052 (3)	169
N4—H4···N2ⁱⁱⁱ	0.96 (3)	1.86 (3)	2.816 (3)	176 (3)
O4—H4A···O2^iv	0.86 (3)	1.93 (3)	2.787 (3)	178 (3)
O4—H4B···O1^v	0.84 (3)	2.11 (5)	2.842 (3)	146 (3)
N5—H5A···O2ⁱ	0.86	2.15	2.898 (3)	146
N5—H5B···O1ⁱⁱⁱ	0.86	2.11	2.931 (3)	159

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₅N₅O₃·H₂O
M_r	271.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	8.2020 (16), 13.889 (3), 11.001 (2)
V (Å³)	1253.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.54 × 0.45 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.957, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	6830, 1193, 1084
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.118, 1.06
No. of reflections	1193
No. of parameters	186
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), 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
O2—H2···O4ⁱ	0.82000	1.90000	2.719 (3)	175
O3—H3A···N3ⁱⁱ	0.82000	2.24000	3.052 (3)	169
N4—H4···N2ⁱⁱⁱ	0.96 (3)	1.86 (3)	2.816 (3)	176 (3)
O4—H4A···O2^iv	0.86 (3)	1.93 (3)	2.787 (3)	178 (3)
O4—H4B···O1^v	0.84 (3)	2.11 (5)	2.842 (3)	146 (3)
N5—H5A···O2ⁱ	0.86000	2.15000	2.898 (3)	146
N5—H5B···O1ⁱⁱⁱ	0.86000	2.11000	2.931 (3)	159

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 20861002), the 973 Plan of China (2009CB526503) and the Open Foundation of the Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) for financial support.

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