4,6-Dimethyl-pyrimidin-2(1H)-one-urea-water (1/1/1).

In the crystal structure of the title compound, C(6)H(8)N(2)O·CH(4)N(2)O·H(2)O, mol-ecules are linked via N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background, see: Zhao et al., (2004 ▶); Zheng et al., (2005 ▶).

Experimental

Crystal data

C6H8N2O·CH4N2O·H2O

M = 202.22

Triclinic,

a = 8.1246 (5) Å

b = 8.4062 (5) Å

c = 8.9268 (9) Å

α = 105.007 (3)°

β = 103.857 (3)°

γ = 114.379 (2)°

V = 493.05 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (2) K

0.22 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.977, T max = 0.998

5424 measured reflections

1728 independent reflections

1439 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.170

S = 1.10

1728 reflections

143 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020928/rk2094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020928/rk2094Isup2.hkl

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

C6H8N2O·CH4N2O·H2O	Z = 2
Mr = 202.22	F000 = 216
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.1246 (5) Å	Cell parameters from 1728 reflections
b = 8.4062 (5) Å	θ = 2.6–25.1º
c = 8.9268 (9) Å	µ = 0.11 mm−1
α = 105.007 (3)º	T = 293 (2) K
β = 103.857 (3)º	Prism, colourless
γ = 114.379 (2)º	0.22 × 0.16 × 0.11 mm
V = 493.05 (7) Å3

Bruker APEXII CCD area-detector diffractometer	1728 independent reflections
Radiation source: Fine–focus sealed tube	1439 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.019
T = 293(2) K	θmax = 25.1º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.977, Tmax = 0.998	k = −8→10
5424 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.0859P)2 + 0.3229P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1728 reflections	Δρmax = 0.45 e Å−3
143 parameters	Δρmin = −0.36 e Å−3
1 restraint	Extinction correction: None
Primary atom site location: Direct

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted < i>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	0.4613 (3)	0.3670 (3)	0.6702 (3)	0.0323 (5)
C2	0.9295 (4)	0.6340 (4)	0.6375 (4)	0.0479 (7)
H2A	0.9052	0.5182	0.5560	0.072*
H2B	1.0477	0.6850	0.7341	0.072*
H2C	0.9443	0.7254	0.5883	0.072*
C3	0.7605 (3)	0.5927 (3)	0.6906 (3)	0.0343 (5)
C4	0.7602 (3)	0.7390 (3)	0.8094 (3)	0.0342 (5)
H4	0.8631	0.8644	0.8538	0.041*
C5	0.6073 (3)	0.6940 (3)	0.8582 (3)	0.0304 (5)
C6	0.5869 (4)	0.8321 (3)	0.9851 (3)	0.0393 (6)
H6A	0.4664	0.7658	0.9983	0.059*
H6B	0.5853	0.9287	0.9473	0.059*
H6C	0.6958	0.8907	1.0913	0.059*
C7	−0.0065 (3)	0.2768 (3)	0.8185 (3)	0.0326 (5)
N1	0.6150 (3)	0.4123 (3)	0.6221 (2)	0.0345 (5)
N2	0.4613 (3)	0.5103 (3)	0.7881 (2)	0.0305 (5)
H2	0.361 (5)	0.477 (4)	0.825 (4)	0.037*
N3	−0.0268 (4)	0.1313 (3)	0.6941 (3)	0.0456 (6)
H3A	0.067 (5)	0.150 (4)	0.657 (4)	0.055*
H3B	−0.135 (5)	0.035 (5)	0.631 (4)	0.055*
N4	−0.1593 (3)	0.2454 (3)	0.8633 (3)	0.0411 (5)
H4A	−0.151 (4)	0.352 (5)	0.938 (4)	0.049*
H4B	−0.269 (5)	0.148 (5)	0.801 (4)	0.049*
O1	0.3211 (2)	0.2007 (2)	0.6121 (2)	0.0431 (5)
O2	0.1517 (2)	0.4327 (2)	0.8930 (2)	0.0383 (5)
O1W	0.5570 (3)	0.0847 (2)	0.3512 (2)	0.0459 (5)
H1WA	0.5959 (10)	0.175 (2)	0.445 (2)	0.055*
H1WB	0.6047 (12)	0.0249 (14)	0.3918 (11)	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.0355 (12)	0.0298 (12)	0.0289 (11)	0.0177 (10)	0.0113 (9)	0.0074 (9)
C2	0.0432 (14)	0.0535 (16)	0.0554 (16)	0.0269 (13)	0.0298 (13)	0.0205 (13)
C3	0.0341 (12)	0.0401 (13)	0.0342 (12)	0.0221 (11)	0.0143 (10)	0.0162 (10)
C4	0.0327 (12)	0.0300 (12)	0.0364 (12)	0.0140 (10)	0.0135 (10)	0.0117 (10)
C5	0.0341 (11)	0.0292 (11)	0.0289 (11)	0.0173 (10)	0.0116 (9)	0.0117 (9)
C6	0.0460 (14)	0.0297 (12)	0.0414 (13)	0.0186 (11)	0.0216 (11)	0.0103 (10)
C7	0.0318 (11)	0.0287 (12)	0.0343 (12)	0.0133 (10)	0.0123 (10)	0.0128 (9)
N1	0.0366 (10)	0.0378 (11)	0.0332 (10)	0.0227 (9)	0.0160 (8)	0.0113 (9)
N2	0.0304 (10)	0.0294 (10)	0.0310 (10)	0.0156 (9)	0.0135 (8)	0.0093 (8)
N3	0.0370 (12)	0.0340 (12)	0.0463 (13)	0.0084 (10)	0.0188 (10)	0.0023 (10)
N4	0.0302 (10)	0.0337 (11)	0.0488 (13)	0.0114 (9)	0.0167 (10)	0.0085 (10)
O1	0.0404 (10)	0.0296 (9)	0.0449 (10)	0.0129 (8)	0.0169 (8)	0.0025 (7)
O2	0.0328 (9)	0.0305 (9)	0.0433 (10)	0.0113 (7)	0.0184 (7)	0.0078 (7)
O1W	0.0477 (10)	0.0437 (10)	0.0396 (10)	0.0248 (9)	0.0124 (8)	0.0091 (8)

C1—O1	1.244 (3)	C6—H6A	0.9600
C1—N1	1.356 (3)	C6—H6B	0.9600
C1—N2	1.379 (3)	C6—H6C	0.9600
C2—C3	1.495 (3)	C7—O2	1.249 (3)
C2—H2A	0.9600	C7—N4	1.339 (3)
C2—H2B	0.9600	C7—N3	1.341 (3)
C2—H2C	0.9600	N2—H2	0.92 (3)
C3—N1	1.329 (3)	N3—H3A	0.87 (3)
C3—C4	1.401 (3)	N3—H3B	0.83 (3)
C4—C5	1.354 (3)	N4—H4A	0.93 (3)
C4—H4	0.9300	N4—H4B	0.83 (3)
C5—N2	1.347 (3)	O1W—H1WA	0.850 (11)
C5—C6	1.492 (3)	O1W—H1WB	0.850 (11)
O1—C1—N1	122.19 (19)	C5—C6—H6B	109.5
O1—C1—N2	119.09 (19)	H6A—C6—H6B	109.5
N1—C1—N2	118.7 (2)	C5—C6—H6C	109.5
C3—C2—H2A	109.5	H6A—C6—H6C	109.5
C3—C2—H2B	109.5	H6B—C6—H6C	109.5
H2A—C2—H2B	109.5	O2—C7—N4	121.7 (2)
C3—C2—H2C	109.5	O2—C7—N3	120.9 (2)
H2A—C2—H2C	109.5	N4—C7—N3	117.3 (2)
H2B—C2—H2C	109.5	C3—N1—C1	118.88 (19)
N1—C3—C4	122.5 (2)	C5—N2—C1	123.10 (19)
N1—C3—C2	116.8 (2)	C5—N2—H2	118.8 (19)
C4—C3—C2	120.7 (2)	C1—N2—H2	117.9 (19)
C5—C4—C3	118.7 (2)	C7—N3—H3A	119 (2)
C5—C4—H4	120.6	C7—N3—H3B	122 (2)
C3—C4—H4	120.6	H3A—N3—H3B	116 (3)
N2—C5—C4	118.0 (2)	C7—N4—H4A	116.4 (19)
N2—C5—C6	116.75 (19)	C7—N4—H4B	119 (2)
C4—C5—C6	125.2 (2)	H4A—N4—H4B	120 (3)
C5—C6—H6A	109.5	H1WA—O1W—H1WB	96.3 (12)
N1—C3—C4—C5	1.1 (4)	O1—C1—N1—C3	−179.4 (2)
C2—C3—C4—C5	−177.7 (2)	N2—C1—N1—C3	0.3 (3)
C3—C4—C5—N2	−0.8 (3)	C4—C5—N2—C1	0.3 (3)
C3—C4—C5—C6	178.9 (2)	C6—C5—N2—C1	−179.4 (2)
C4—C3—N1—C1	−0.8 (3)	O1—C1—N2—C5	179.7 (2)
C2—C3—N1—C1	178.0 (2)	N1—C1—N2—C5	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.92 (3)	1.87 (3)	2.779 (2)	172 (3)
N3—H3A···O1	0.87 (3)	2.09 (3)	2.953 (3)	169 (3)
N3—H3B···O1i	0.83 (3)	2.16 (3)	2.896 (3)	149 (3)
N4—H4A···O2ii	0.93 (3)	2.04 (3)	2.968 (3)	174 (3)
N4—H4B···O1Wi	0.83 (3)	2.12 (4)	2.948 (3)	175 (3)
O1W—H1WA···N1	0.850 (11)	2.121 (15)	2.930 (2)	159.1 (13)
O1W—H1WB···O1iii	0.850 (11)	2.209 (11)	3.009 (3)	156.9 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.92 (3)	1.87 (3)	2.779 (2)	172 (3)
N3—H3A⋯O1	0.87 (3)	2.09 (3)	2.953 (3)	169 (3)
N3—H3B⋯O1i	0.83 (3)	2.16 (3)	2.896 (3)	149 (3)
N4—H4A⋯O2ii	0.93 (3)	2.04 (3)	2.968 (3)	174 (3)
N4—H4B⋯O1Wi	0.83 (3)	2.12 (4)	2.948 (3)	175 (3)
O1W—H1WA⋯N1	0.850 (11)	2.121 (15)	2.930 (2)	159.1 (13)
O1W—H1WB⋯O1iii	0.850 (11)	2.209 (11)	3.009 (3)	156.9 (3)

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