2-Amino-9-[(1S,3R,4S)-4-hydr­oxy-3-hydroxy­methyl-2-methyl­enecyclo­pent­yl]-1,9-dihydro-6H-purin-6-one monohydrate

Jiang, B.; Liu, Z.

doi:10.1107/S1600536809032966

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2232

doi:10.1107/S1600536809032966

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2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one monohydrate

Bin Jiang ^a and Zhilu Liu ^b ^*

^aDepartment of Pharmacy, Shandong Medical College, Jinan 250002, People's Republic of China, and ^bState Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 73000, People's Republic of China
^*Correspondence e-mail: liuzhilu2009@yahoo.com.cn

(Received 4 August 2009; accepted 19 August 2009; online 26 August 2009)

In the crystal of the title compound, C₁₂H₁₅N₅O₃·H₂O, the component species are linked by N—H⋯N, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming a three-dimesnional network.

Related literature

For background, see: Czarnik (2008 ).

Experimental

Crystal data

C₁₂H₁₅N₅O₃·H₂O
M_r = 295.31
Orthorhombic, C 222₁
a = 6.9986 (10) Å
b = 11.6229 (10) Å
c = 33.932 (3) Å
V = 2760.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 273 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.987, T_max = 0.991
6725 measured reflections
1377 independent reflections
1270 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.00
1377 reflections
204 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 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
O1—H1⋯N4ⁱ	0.82	2.04	2.857 (2)	172
O2—H2A⋯O1Wⁱⁱ	0.82	1.83	2.639 (3)	169
N3—H3B⋯O3ⁱⁱⁱ	0.86	2.24	3.039 (3)	154
N5—H5C⋯N2ⁱⁱⁱ	0.97 (3)	1.86 (3)	2.829 (3)	177 (3)
O1W—H2W⋯O1^iv	0.819 (19)	2.113 (10)	2.900 (3)	161 (3)
O1W—H1W⋯O2^v	0.821 (12)	2.000 (16)	2.783 (3)	159 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x+1, y, z; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, -y, -z+1; (v) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); 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: 10.1107/S1600536809032966/hb5032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032966/hb5032Isup2.hkl

checkCIF report

Comment top

The research of anti-hepatitis B virus (anti-HBV) drug has long been one of the serious diseases threatening human's health, and thus searching for effective medicines to cure such illness has led to significant interest over the past decades (Czarnik, 2008). In this article, we report the crystal structural characterization of 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3- (hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one.

As shown in figure 1, the asymmetrical unit contains one 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2 -methylenecyclopentyl]-6H-purin-6-one and one water molecule. In addition, it is noteworthy that the multipoint hydrogen-bonding links also exist between the hydrogen atoms including N3—H3B···O3, 3.039 (3) Å; O1—H1···N4, 2.861 (2) Å; O2—H2A···O1W, 2.634 (2) Å; O1W—H2W···O1, 2.899 (3) Å; O1W—H1W···O2, 2.786 (3) Å; this may make a contribution to stabilizing the chain structure, shown in figure 2.

Related literature top

For background, see: Czarnik (2008).

Experimental top

The reaction was performed in a 25-ml Teflon-lined stainless steel vessel. The powder of 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2 -methylenecyclopentyl]-6H-purin-6-one (1 mmol) in 5 ml water and 5 ml etanol was heated to 443 K and kept at this temperature for one day. Upon cooling, colourless blocks of (I) were recovered. Anal. Calc. for C₁₂H₁₇N₅O₄: C 48.76, H 5.08, N 23.70%; Found: 48.68, H 5.05, N 23.66%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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. A view of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of (I) packing strcuture.

2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl- 2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one monohydrate top

Crystal data top

C₁₂H₁₅N₅O₃·H₂O	F(000) = 1248
M_r = 295.31	D_x = 1.421 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 1377 reflections
a = 6.9986 (10) Å	θ = 3.4–25.0°
b = 11.6229 (10) Å	µ = 0.11 mm⁻¹
c = 33.932 (3) Å	T = 273 K
V = 2760.1 (5) Å³	Block, colorless
Z = 8	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	1377 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.987, T_max = 0.991	k = −11→13
6725 measured reflections	l = −33→40

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.055P)² + 0.4836P] where P = (F_o² + 2F_c²)/3
1377 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 0.16 e Å⁻³
4 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₂H₁₅N₅O₃·H₂O	V = 2760.1 (5) Å³
M_r = 295.31	Z = 8
Orthorhombic, C222₁	Mo Kα radiation
a = 6.9986 (10) Å	µ = 0.11 mm⁻¹
b = 11.6229 (10) Å	T = 273 K
c = 33.932 (3) Å	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	1377 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1270 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.030
6725 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	4 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.16 e Å⁻³
1377 reflections	Δρ_min = −0.18 e Å⁻³
204 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	0.5675 (3)	−0.0420 (2)	0.57539 (7)	0.0345 (5)
H1A	0.5960	−0.1042	0.5573	0.041*
H1B	0.6267	−0.0597	0.6005	0.041*
C2	0.6493 (3)	0.0717 (2)	0.55918 (6)	0.0297 (5)
H2	0.5838	0.0930	0.5347	0.036*
C3	0.6333 (3)	0.16870 (18)	0.58921 (6)	0.0269 (5)
C4	0.8242 (3)	0.18411 (18)	0.60945 (6)	0.0267 (5)
H4	0.8800	0.2562	0.5999	0.032*
C5	0.9461 (3)	0.0841 (2)	0.59303 (7)	0.0314 (5)
H5A	1.0796	0.1060	0.5911	0.038*
H5B	0.9355	0.0164	0.6096	0.038*
C6	0.8611 (3)	0.0616 (2)	0.55207 (6)	0.0306 (5)
H6	0.8961	−0.0146	0.5420	0.037*
C7	0.7957 (4)	0.10135 (19)	0.67986 (7)	0.0364 (6)
H7	0.7995	0.0242	0.6727	0.044*
C8	0.8003 (3)	0.29145 (18)	0.67510 (6)	0.0293 (5)
C9	0.7746 (4)	0.25703 (19)	0.71395 (7)	0.0338 (5)
C10	0.7892 (3)	0.48170 (19)	0.68899 (6)	0.0327 (5)
C11	0.7511 (4)	0.34291 (19)	0.74423 (7)	0.0353 (5)
C12	0.4843 (4)	0.2341 (2)	0.59666 (9)	0.0445 (6)
H12A	0.4935	0.2931	0.6151	0.053*
H12B	0.3697	0.2215	0.5835	0.053*
N1	0.8142 (3)	0.19086 (16)	0.65304 (5)	0.0310 (4)
N2	0.7723 (3)	0.13654 (16)	0.71662 (6)	0.0395 (5)
N3	0.7949 (3)	0.59520 (16)	0.67918 (6)	0.0424 (5)
H3A	0.8106	0.6153	0.6550	0.051*
H3B	0.7829	0.6468	0.6972	0.051*
N4	0.8083 (3)	0.40206 (16)	0.66034 (5)	0.0331 (5)
N5	0.7614 (3)	0.45538 (16)	0.72814 (5)	0.0362 (5)
O1	0.3698 (2)	−0.03239 (15)	0.58020 (5)	0.0387 (4)
H1	0.3405	−0.0525	0.6026	0.058*
O2	0.9107 (3)	0.15191 (15)	0.52463 (5)	0.0422 (5)
H2A	1.0233	0.1455	0.5183	0.063*
O3	0.7248 (3)	0.32814 (15)	0.78032 (5)	0.0499 (5)
O1W	0.2565 (3)	0.13435 (18)	0.49421 (6)	0.0500 (5)
H2W	0.274 (5)	0.0919 (17)	0.4753 (5)	0.069 (12)*
H1W	0.274 (7)	0.2029 (6)	0.4897 (8)	0.102 (16)*
H5C	0.754 (5)	0.518 (2)	0.7470 (8)	0.080 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0340 (12)	0.0315 (13)	0.0380 (13)	−0.0029 (10)	−0.0012 (10)	−0.0008 (11)
C2	0.0331 (12)	0.0313 (12)	0.0246 (10)	−0.0001 (10)	−0.0015 (9)	0.0007 (9)
C3	0.0304 (11)	0.0236 (11)	0.0269 (10)	0.0008 (9)	0.0050 (9)	0.0052 (9)
C4	0.0325 (11)	0.0223 (11)	0.0252 (10)	−0.0022 (9)	0.0036 (8)	−0.0009 (9)
C5	0.0267 (11)	0.0321 (12)	0.0355 (12)	0.0022 (10)	0.0017 (9)	−0.0033 (10)
C6	0.0371 (12)	0.0267 (11)	0.0282 (11)	0.0004 (10)	0.0072 (9)	−0.0033 (9)
C7	0.0539 (15)	0.0242 (11)	0.0312 (12)	0.0028 (11)	0.0004 (11)	0.0012 (9)
C8	0.0357 (12)	0.0269 (11)	0.0255 (11)	−0.0007 (10)	0.0004 (9)	−0.0028 (9)
C9	0.0461 (13)	0.0291 (11)	0.0260 (11)	−0.0006 (11)	0.0023 (11)	0.0004 (9)
C10	0.0390 (13)	0.0317 (12)	0.0272 (11)	−0.0021 (11)	0.0011 (10)	−0.0027 (9)
C11	0.0455 (13)	0.0346 (11)	0.0258 (12)	−0.0019 (12)	0.0012 (10)	0.0007 (9)
C12	0.0395 (14)	0.0359 (14)	0.0580 (17)	0.0044 (12)	0.0021 (12)	−0.0019 (12)
N1	0.0416 (11)	0.0256 (9)	0.0260 (9)	−0.0015 (9)	0.0005 (8)	−0.0019 (8)
N2	0.0594 (13)	0.0299 (10)	0.0292 (10)	−0.0009 (10)	0.0029 (10)	0.0047 (8)
N3	0.0707 (15)	0.0281 (10)	0.0284 (10)	−0.0006 (11)	0.0061 (10)	−0.0004 (8)
N4	0.0477 (12)	0.0273 (10)	0.0243 (9)	−0.0005 (9)	0.0033 (9)	−0.0017 (8)
N5	0.0544 (12)	0.0298 (10)	0.0242 (9)	−0.0007 (10)	0.0036 (9)	−0.0041 (8)
O1	0.0332 (9)	0.0438 (10)	0.0389 (9)	−0.0070 (8)	0.0015 (7)	0.0058 (8)
O2	0.0431 (10)	0.0434 (10)	0.0401 (9)	0.0010 (8)	0.0184 (8)	0.0074 (8)
O3	0.0824 (14)	0.0433 (10)	0.0239 (8)	−0.0004 (10)	0.0077 (8)	0.0016 (7)
O1W	0.0490 (11)	0.0500 (12)	0.0512 (12)	0.0011 (11)	0.0141 (9)	0.0074 (10)

Geometric parameters (Å, º) top

C1—O1	1.398 (3)	C8—N4	1.381 (3)
C1—C2	1.542 (3)	C8—C9	1.389 (3)
C1—H1A	0.9700	C8—N1	1.392 (3)
C1—H1B	0.9700	C9—N2	1.403 (3)
C2—C6	1.506 (3)	C9—C11	1.442 (3)
C2—C3	1.524 (3)	C10—N4	1.349 (3)
C2—H2	0.9800	C10—N3	1.361 (3)
C3—C12	1.316 (3)	C10—N5	1.377 (3)
C3—C4	1.513 (3)	C11—O3	1.250 (3)
C4—N1	1.483 (2)	C11—N5	1.418 (3)
C4—C5	1.546 (3)	C12—H12A	0.9300
C4—H4	0.9800	C12—H12B	0.9300
C5—C6	1.534 (3)	N3—H3A	0.8600
C5—H5A	0.9700	N3—H3B	0.8600
C5—H5B	0.9700	N5—H5C	0.97 (3)
C6—O2	1.445 (3)	O1—H1	0.8200
C6—H6	0.9800	O2—H2A	0.8200
C7—N2	1.323 (3)	O1W—H2W	0.819 (19)
C7—N1	1.388 (3)	O1W—H1W	0.821 (12)
C7—H7	0.9300

O1—C1—C2	109.91 (19)	N2—C7—N1	113.4 (2)
O1—C1—H1A	109.7	N2—C7—H7	123.3
C2—C1—H1A	109.7	N1—C7—H7	123.3
O1—C1—H1B	109.7	N4—C8—C9	128.1 (2)
C2—C1—H1B	109.7	N4—C8—N1	125.74 (19)
H1A—C1—H1B	108.2	C9—C8—N1	106.11 (19)
C6—C2—C3	103.73 (19)	C8—C9—N2	110.5 (2)
C6—C2—C1	110.8 (2)	C8—C9—C11	119.4 (2)
C3—C2—C1	111.62 (18)	N2—C9—C11	130.0 (2)
C6—C2—H2	110.2	N4—C10—N3	119.1 (2)
C3—C2—H2	110.2	N4—C10—N5	123.8 (2)
C1—C2—H2	110.2	N3—C10—N5	117.10 (19)
C12—C3—C4	123.0 (2)	O3—C11—N5	120.7 (2)
C12—C3—C2	127.9 (2)	O3—C11—C9	128.3 (2)
C4—C3—C2	109.04 (18)	N5—C11—C9	110.97 (18)
N1—C4—C3	114.69 (17)	C3—C12—H12A	120.0
N1—C4—C5	115.16 (18)	C3—C12—H12B	120.0
C3—C4—C5	103.58 (17)	H12A—C12—H12B	120.0
N1—C4—H4	107.7	C7—N1—C8	105.70 (17)
C3—C4—H4	107.7	C7—N1—C4	128.21 (18)
C5—C4—H4	107.7	C8—N1—C4	125.75 (18)
C6—C5—C4	103.91 (17)	C7—N2—C9	104.25 (19)
C6—C5—H5A	111.0	C10—N3—H3A	120.0
C4—C5—H5A	111.0	C10—N3—H3B	120.0
C6—C5—H5B	111.0	H3A—N3—H3B	120.0
C4—C5—H5B	111.0	C10—N4—C8	111.93 (18)
H5A—C5—H5B	109.0	C10—N5—C11	125.68 (18)
O2—C6—C2	106.42 (19)	C10—N5—H5C	118 (2)
O2—C6—C5	111.52 (19)	C11—N5—H5C	116 (2)
C2—C6—C5	102.89 (18)	C1—O1—H1	109.5
O2—C6—H6	111.8	C6—O2—H2A	109.5
C2—C6—H6	111.8	H2W—O1W—H1W	115 (2)
C5—C6—H6	111.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4ⁱ	0.82	2.04	2.857 (2)	172
O2—H2A···O1Wⁱⁱ	0.82	1.83	2.639 (3)	169
N3—H3B···O3ⁱⁱⁱ	0.86	2.24	3.039 (3)	154
N5—H5C···N2ⁱⁱⁱ	0.97 (3)	1.86 (3)	2.829 (3)	177 (3)
O1W—H2W···O1^iv	0.82 (2)	2.11 (1)	2.900 (3)	161 (3)
O1W—H1W···O2^v	0.82 (1)	2.00 (2)	2.783 (3)	159 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅N₅O₃·H₂O
M_r	295.31
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	273
a, b, c (Å)	6.9986 (10), 11.6229 (10), 33.932 (3)
V (Å³)	2760.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	6725, 1377, 1270
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.00
No. of reflections	1377
No. of parameters	204
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)	0.16, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), 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
O1—H1···N4ⁱ	0.82	2.04	2.857 (2)	172
O2—H2A···O1Wⁱⁱ	0.82	1.83	2.639 (3)	169
N3—H3B···O3ⁱⁱⁱ	0.86	2.24	3.039 (3)	154
N5—H5C···N2ⁱⁱⁱ	0.97 (3)	1.86 (3)	2.829 (3)	177 (3)
O1W—H2W···O1^iv	0.819 (19)	2.113 (10)	2.900 (3)	161 (3)
O1W—H1W···O2^v	0.821 (12)	2.000 (16)	2.783 (3)	159 (4)

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

Acknowledgements

This work was supported by the Chinese Academy of Sciences (`Hundred Talents Program') and the Ministry of Science and Technology of China (project of `973' plan, No. 2007CB607606).

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Czarnik, A. W. (2008). J. Comb. Chem. 10, 1–2. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 9| September 2009| Page o2232

doi:10.1107/S1600536809032966

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Amino-9-[(1S,3R,4S)-4-hydr­­oxy-3-hy­droxy­methyl-2-methyl­ene­cyclo­pent­yl]-1,9-di­hydro-6H-purin-6-one monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one monohydrate