9-[4-Hydr-oxy-3-(hydroxy-meth-yl)but-yl]guanine monohydrate.

In the mol-ecular structure of the title compound, also named penciclovir monohydrate, C(10)H(15)N(5)O(3)·H(2)O, the 4-hydr-oxy-3-hydroxy-methyl-but-1-yl group is connected to guanine through an N atom of the imidazole ring. Water mol-ecules stabilize the mol-ecular packing by forming O-H⋯O hydrogen bonds. A three-dimensional network is generated via inter-molecular 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 n class="Chemical">penciclovir, see: Abdel-Hag et al. (2006 ▶); Andrei et al. (2004 ▶); Schmid-Wendtner & Korting (2004 ▶); Smith et al. (2001 ▶).

Experimental

Crystal data

C10H15N5O3·n class="Chemical">H2O

M = 271.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.118

S = 1.06

1193 reflections

186 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT-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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043980/ds2005sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043980/ds2005Isup2.hkl

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

C10H15N5O3·H2O	F(000) = 576
Mr = 271.29	Dx = 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

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

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(Fo2) + (0.0604P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
1193 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.15 e Å−3
4 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O2iv	0.86 (3)	1.93 (3)	2.787 (3)	178 (3)
O4—H4B···O1v	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

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⋯O2iv	0.86 (3)	1.93 (3)	2.787 (3)	178 (3)
O4—H4B⋯O1v	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) ; (ii) ; (iii) ; (iv) ; (v) .