N-(2-Amino-4,6-dihydroxypyrimidin-5-yl)acetamide dihydrate.

The title compound, C(6)H(8)N(4)O(3)·2H(2)O, which crystallized as a dihydrate, has two almost planar segments viz. the pyrimidine ring and the C-N-C(=O)-C group [maxmum deviations of 0.020 (2) and 0.014 (2) Å, respectively], with a dihedral angle of 87.45°. In the crystal, the components are linked by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the biological properties of pyrimidine compounds see: Marchal et al. (2010 ▶); Giandinoto et al. (1996 ▶); Sun et al. (2006 ▶). For related structures, see: Glidewell et al. (2003 ▶); Nakayama et al. (2004 ▶); Quesada et al. (2004 ▶); Hockova et al. (2003 ▶).

Experimental

Crystal data

C6H8N4O3·2H2O

M = 220.20

Monoclinic,

a = 9.5501 (12) Å

b = 12.2161 (13) Å

c = 8.5324 (8) Å

β = 98.708 (1)°

V = 983.96 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.23 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.971, T max = 0.987

5002 measured reflections

1727 independent reflections

1082 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 0.85

1727 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2002 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811034441/fl2354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034441/fl2354Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034441/fl2354Isup3.cml

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

C6H8N4O3·2H2O	F(000) = 464
Mr = 220.20	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5501 (12) Å	Cell parameters from 1089 reflections
b = 12.2161 (13) Å	θ = 2.7–26.2°
c = 8.5324 (8) Å	µ = 0.13 mm−1
β = 98.708 (1)°	T = 298 K
V = 983.96 (19) Å3	Cuboid, colorless
Z = 4	0.23 × 0.15 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	1727 independent reflections
Radiation source: fine-focus sealed tube	1082 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 2.2°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −14→13
Tmin = 0.971, Tmax = 0.987	l = −9→10
5002 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 0.85	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2581P] where P = (Fo2 + 2Fc2)/3
1727 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.26 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
O4	0.21459 (17)	0.66228 (13)	0.37653 (19)	0.0498 (5)
N1	0.51891 (18)	0.27137 (14)	0.8076 (2)	0.0336 (5)
H1	0.5490	0.2108	0.8520	0.040*
N2	0.53066 (18)	0.45908 (14)	0.7961 (2)	0.0350 (5)
H2	0.5664	0.5196	0.8351	0.042*
N3	0.68269 (19)	0.36480 (15)	0.9877 (2)	0.0403 (5)
H3A	0.7194	0.4256	1.0247	0.048*
H3B	0.7129	0.3038	1.0305	0.048*
N4	0.25806 (19)	0.36468 (14)	0.4697 (2)	0.0364 (5)
H4	0.2839	0.3634	0.3774	0.044*
O1	0.38963 (16)	0.55753 (12)	0.60969 (18)	0.0443 (5)
O2	0.35840 (16)	0.17282 (12)	0.64300 (17)	0.0408 (4)
O3	0.07419 (17)	0.37021 (14)	0.60637 (19)	0.0526 (5)
H4A	0.2598	0.6153	0.4382	0.063*
H4B	0.1272	0.6500	0.3778	0.063*
O5	0.1825 (2)	0.06285 (14)	0.4167 (2)	0.0641 (6)
H5A	0.2207	0.1168	0.4697	0.077*
H5B	0.1527	0.0876	0.3245	0.077*
C1	0.5807 (2)	0.36517 (17)	0.8661 (2)	0.0313 (5)
C2	0.4238 (2)	0.46472 (18)	0.6633 (2)	0.0327 (5)
C3	0.3655 (2)	0.36483 (17)	0.6053 (2)	0.0320 (5)
C4	0.4087 (2)	0.26646 (18)	0.6789 (2)	0.0314 (5)
C5	0.1185 (2)	0.36648 (18)	0.4780 (3)	0.0377 (6)
C6	0.0201 (3)	0.3621 (2)	0.3226 (3)	0.0566 (8)
H6A	−0.0314	0.2944	0.3152	0.085*
H6B	0.0743	0.3670	0.2367	0.085*
H6C	−0.0452	0.4222	0.3166	0.085*

	U11	U22	U33	U12	U13	U23
O4	0.0423 (10)	0.0475 (11)	0.0557 (11)	−0.0018 (8)	−0.0048 (8)	0.0086 (8)
N1	0.0395 (11)	0.0234 (10)	0.0348 (10)	0.0006 (8)	−0.0042 (9)	0.0052 (8)
N2	0.0390 (11)	0.0231 (10)	0.0398 (11)	−0.0015 (8)	−0.0039 (9)	−0.0026 (8)
N3	0.0443 (12)	0.0300 (10)	0.0418 (11)	0.0004 (9)	−0.0090 (9)	−0.0010 (9)
N4	0.0418 (12)	0.0348 (11)	0.0312 (10)	0.0005 (9)	0.0009 (8)	−0.0002 (8)
O1	0.0548 (11)	0.0217 (9)	0.0508 (10)	0.0016 (7)	−0.0104 (8)	0.0031 (7)
O2	0.0472 (10)	0.0251 (9)	0.0452 (9)	−0.0033 (7)	−0.0092 (7)	0.0004 (7)
O3	0.0398 (10)	0.0727 (13)	0.0433 (10)	−0.0004 (9)	−0.0004 (8)	−0.0034 (9)
O5	0.0867 (14)	0.0427 (11)	0.0521 (11)	−0.0023 (10)	−0.0241 (10)	−0.0001 (9)
C1	0.0329 (12)	0.0273 (12)	0.0328 (11)	0.0001 (10)	0.0020 (10)	−0.0005 (10)
C2	0.0335 (12)	0.0301 (13)	0.0336 (12)	0.0022 (10)	0.0019 (10)	0.0008 (10)
C3	0.0344 (12)	0.0277 (12)	0.0319 (12)	0.0004 (10)	−0.0017 (10)	−0.0008 (10)
C4	0.0316 (12)	0.0290 (13)	0.0331 (12)	−0.0020 (10)	0.0029 (10)	−0.0036 (10)
C5	0.0427 (15)	0.0293 (12)	0.0385 (13)	0.0016 (11)	−0.0025 (11)	−0.0034 (10)
C6	0.0507 (16)	0.0645 (19)	0.0473 (15)	0.0095 (13)	−0.0159 (13)	−0.0124 (13)

O4—H4A	0.8504	N4—H4	0.8600
O4—H4B	0.8494	O1—C2	1.247 (2)
N1—C1	1.350 (3)	O2—C4	1.260 (2)
N1—C4	1.403 (2)	O3—C5	1.234 (3)
N1—H1	0.8600	O5—H5A	0.8501
N2—C1	1.347 (3)	O5—H5B	0.8501
N2—C2	1.407 (2)	C2—C3	1.400 (3)
N2—H2	0.8600	C3—C4	1.389 (3)
N3—C1	1.312 (3)	C5—C6	1.505 (3)
N3—H3A	0.8600	C6—H6A	0.9600
N3—H3B	0.8600	C6—H6B	0.9600
N4—C5	1.345 (3)	C6—H6C	0.9600
N4—C3	1.426 (3)
H4A—O4—H4B	106.3	O1—C2—N2	117.21 (19)
C1—N1—C4	124.06 (18)	C3—C2—N2	116.30 (19)
C1—N1—H1	118.0	C4—C3—C2	121.27 (19)
C4—N1—H1	118.0	C4—C3—N4	119.58 (19)
C1—N2—C2	124.33 (18)	C2—C3—N4	119.14 (19)
C1—N2—H2	117.8	O2—C4—C3	126.82 (19)
C2—N2—H2	117.8	O2—C4—N1	116.23 (19)
C1—N3—H3A	120.0	C3—C4—N1	116.95 (19)
C1—N3—H3B	120.0	O3—C5—N4	121.5 (2)
H3A—N3—H3B	120.0	O3—C5—C6	122.1 (2)
C5—N4—C3	123.67 (19)	N4—C5—C6	116.4 (2)
C5—N4—H4	118.2	C5—C6—H6A	109.5
C3—N4—H4	118.2	C5—C6—H6B	109.5
H5A—O5—H5B	105.9	H6A—C6—H6B	109.5
N3—C1—N2	121.66 (19)	C5—C6—H6C	109.5
N3—C1—N1	121.37 (19)	H6A—C6—H6C	109.5
N2—C1—N1	116.96 (17)	H6B—C6—H6C	109.5
O1—C2—C3	126.5 (2)
C2—N2—C1—N3	178.5 (2)	C5—N4—C3—C4	85.7 (3)
C2—N2—C1—N1	−2.9 (3)	C5—N4—C3—C2	−93.2 (3)
C4—N1—C1—N3	179.4 (2)	C2—C3—C4—O2	175.6 (2)
C4—N1—C1—N2	0.9 (3)	N4—C3—C4—O2	−3.3 (3)
C1—N2—C2—O1	−178.93 (19)	C2—C3—C4—N1	−3.7 (3)
C1—N2—C2—C3	1.6 (3)	N4—C3—C4—N1	177.38 (19)
O1—C2—C3—C4	−177.5 (2)	C1—N1—C4—O2	−177.07 (19)
N2—C2—C3—C4	1.9 (3)	C1—N1—C4—C3	2.4 (3)
O1—C2—C3—N4	1.4 (3)	C3—N4—C5—O3	1.2 (3)
N2—C2—C3—N4	−179.17 (18)	C3—N4—C5—C6	−178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.98	2.810 (2)	164.
N2—H2···O2ii	0.86	2.00	2.836 (2)	163.
N3—H3A···O5ii	0.86	1.95	2.803 (2)	172.
N3—H3B···O4i	0.86	1.98	2.843 (2)	178.
N4—H4···O2iii	0.86	2.27	3.115 (2)	170.
O4—H4A···O1	0.85	1.90	2.717 (2)	159.
O4—H4B···O3iv	0.85	1.96	2.812 (2)	176.
O5—H5A···O2	0.85	1.95	2.716 (2)	150.
O5—H5B···O3iii	0.85	1.97	2.814 (2)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.98	2.810 (2)	164
N2—H2⋯O2ii	0.86	2.00	2.836 (2)	163
N3—H3A⋯O5ii	0.86	1.95	2.803 (2)	172
N3—H3B⋯O4i	0.86	1.98	2.843 (2)	178
N4—H4⋯O2iii	0.86	2.27	3.115 (2)	170
O4—H4A⋯O1	0.85	1.90	2.717 (2)	159
O4—H4B⋯O3iv	0.85	1.96	2.812 (2)	176
O5—H5A⋯O2	0.85	1.95	2.716 (2)	150
O5—H5B⋯O3iii	0.85	1.97	2.814 (2)	174

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .