2,6-Diamino-4-oxo-3,4-dihydropyrim-idin-1-ium chloride dihydrate.

In the crystal structure of the title compound, C(4)H(7)N(4)O(+)·Cl(-)·2H(2)O, adjacent cations are connected to one another through N-H⋯O hydrogen bonds, forming infinite chains along the b axis. These chains are further hydrogen bonded to the chloride anions and water mol-ecules, resulting in a three-dimensional network. The pyrimidine rings of adjacent mol-ecules are arranged in an anti-parallel manner above each other with centroid-centroid distances of 3.435 (1) Å, indicative of π-π inter-actions.

Related literature

For related structures, see: Wijaya et al. (2004 ▶); Muthiah et al. (2004 ▶).

Experimental

Crystal data

C4H7N4O+·Cl−·2H2O

M = 198.62

Monoclinic,

a = 20.4162 (4) Å

b = 6.6030 (1) Å

c = 12.8876 (2) Å

β = 107.903 (1)°

V = 1653.23 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.44 mm−1

T = 100 K

0.35 × 0.19 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.862, T max = 0.966

4405 measured reflections

1488 independent reflections

1352 reflections with (I) > 2.0σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.066

S = 1.05

1488 reflections

139 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810031557/pv2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031557/pv2317Isup2.hkl

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

C4H7N4O+·Cl−·2H2O	F(000) = 832
Mr = 198.62	Dx = 1.596 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2897 reflections
a = 20.4162 (4) Å	θ = 3.3–30.5°
b = 6.6030 (1) Å	µ = 0.44 mm−1
c = 12.8876 (2) Å	T = 100 K
β = 107.903 (1)°	Block, yellow
V = 1653.23 (5) Å3	0.35 × 0.19 × 0.08 mm
Z = 8

Bruker APEXII CCD diffractometer	1488 independent reflections
Radiation source: fine-focus sealed tube	1352 reflections with (I) > 2.0σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.862, Tmax = 0.966	k = −7→7
4405 measured reflections	l = −15→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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0327P)2 + 1.7645P] where P = (Fo2 + 2Fc2)/3
1488 reflections	(Δ/σ)max = 0.001
139 parameters	Δρmax = 0.22 e Å−3
10 restraints	Δρmin = −0.25 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
Cl1	0.485357 (17)	0.19327 (5)	0.09794 (3)	0.01545 (13)
O2	0.58753 (5)	0.85326 (16)	0.25118 (9)	0.0160 (2)
H8	0.5728 (9)	0.823 (3)	0.3011 (14)	0.024*
H9	0.5575 (8)	0.910 (3)	0.2042 (14)	0.024*
O3	0.55365 (6)	0.66656 (18)	0.41849 (10)	0.0223 (3)
H10	0.5424 (10)	0.545 (2)	0.4079 (16)	0.033*
H11	0.5331 (10)	0.709 (3)	0.4617 (15)	0.033*
O1	0.75583 (5)	−0.12955 (15)	0.37901 (8)	0.0148 (2)
N1	0.68878 (6)	0.14677 (19)	0.31998 (10)	0.0116 (3)
H1	0.6566 (8)	0.062 (2)	0.2953 (13)	0.014*
N2	0.61850 (6)	0.4221 (2)	0.25253 (10)	0.0140 (3)
H2	0.5846 (8)	0.340 (2)	0.2242 (14)	0.017*
H3	0.6124 (8)	0.554 (2)	0.2445 (13)	0.017*
N3	0.73174 (6)	0.47140 (18)	0.35528 (10)	0.0113 (3)
H4	0.7246 (8)	0.601 (2)	0.3510 (13)	0.014*
N4	0.84541 (6)	0.53639 (19)	0.44953 (10)	0.0145 (3)
H5	0.8853 (8)	0.496 (3)	0.4852 (13)	0.017*
H6	0.8359 (9)	0.665 (2)	0.4492 (14)	0.017*
C1	0.75285 (7)	0.0589 (2)	0.37417 (11)	0.0118 (3)
C2	0.67858 (7)	0.3467 (2)	0.30834 (11)	0.0111 (3)
C3	0.79694 (7)	0.3985 (2)	0.40909 (11)	0.0113 (3)
C4	0.80775 (7)	0.1923 (2)	0.41736 (12)	0.0125 (3)
H7	0.8525	0.1407	0.4524	0.015*

	U11	U22	U33	U12	U13	U23
Cl1	0.0137 (2)	0.0141 (2)	0.0164 (2)	−0.00100 (13)	0.00153 (14)	−0.00102 (13)
O2	0.0125 (5)	0.0165 (6)	0.0180 (6)	−0.0001 (4)	0.0033 (4)	0.0016 (4)
O3	0.0300 (7)	0.0152 (6)	0.0253 (6)	−0.0055 (5)	0.0137 (5)	−0.0032 (5)
O1	0.0153 (5)	0.0082 (5)	0.0191 (6)	0.0004 (4)	0.0027 (4)	0.0006 (4)
N1	0.0094 (6)	0.0100 (6)	0.0137 (6)	−0.0021 (5)	0.0012 (5)	−0.0012 (5)
N2	0.0106 (6)	0.0100 (6)	0.0192 (7)	−0.0012 (5)	0.0016 (5)	−0.0003 (5)
N3	0.0117 (6)	0.0077 (6)	0.0134 (6)	0.0006 (5)	0.0025 (5)	0.0004 (5)
N4	0.0114 (6)	0.0099 (6)	0.0190 (7)	0.0000 (5)	−0.0003 (5)	−0.0007 (5)
C1	0.0143 (7)	0.0125 (7)	0.0095 (7)	0.0016 (6)	0.0049 (5)	0.0002 (6)
C2	0.0128 (7)	0.0119 (7)	0.0097 (7)	−0.0009 (5)	0.0050 (6)	−0.0007 (5)
C3	0.0117 (7)	0.0136 (7)	0.0087 (7)	−0.0003 (6)	0.0034 (5)	0.0001 (5)
C4	0.0107 (7)	0.0127 (7)	0.0128 (7)	0.0016 (6)	0.0014 (6)	0.0005 (6)

O2—H8	0.815 (15)	N2—H3	0.882 (14)
O2—H9	0.809 (15)	N3—C2	1.3484 (18)
O3—H10	0.832 (16)	N3—C3	1.3845 (18)
O3—H11	0.841 (15)	N3—H4	0.870 (14)
O1—C1	1.2467 (18)	N4—C3	1.3279 (19)
N1—C2	1.3379 (19)	N4—H5	0.846 (14)
N1—C1	1.4048 (18)	N4—H6	0.868 (14)
N1—H1	0.846 (14)	C1—C4	1.399 (2)
N2—C2	1.3142 (18)	C3—C4	1.378 (2)
N2—H2	0.867 (14)	C4—H7	0.9500
H8—O2—H9	108.9 (19)	H5—N4—H6	119.3 (17)
H10—O3—H11	105.1 (19)	O1—C1—C4	125.98 (13)
C2—N1—C1	123.52 (12)	O1—C1—N1	117.43 (13)
C2—N1—H1	122.2 (11)	C4—C1—N1	116.59 (13)
C1—N1—H1	114.3 (11)	N2—C2—N1	121.48 (13)
C2—N2—H2	118.8 (11)	N2—C2—N3	120.10 (13)
C2—N2—H3	120.8 (11)	N1—C2—N3	118.43 (12)
H2—N2—H3	120.4 (16)	N4—C3—C4	124.39 (13)
C2—N3—C3	121.99 (12)	N4—C3—N3	116.34 (13)
C2—N3—H4	118.6 (11)	C4—C3—N3	119.27 (13)
C3—N3—H4	119.4 (11)	C3—C4—C1	120.08 (13)
C3—N4—H5	118.1 (12)	C3—C4—H7	120.0
C3—N4—H6	121.9 (12)	C1—C4—H7	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O2—H8···O3	0.82 (2)	1.97 (2)	2.7503 (17)	161.(2)
O2—H9···Cl1i	0.81 (2)	2.51 (2)	3.2802 (11)	159.(2)
O3—H10···Cl1ii	0.83 (2)	2.39 (2)	3.2158 (12)	173.(2)
O3—H11···Cl1iii	0.84 (2)	2.35 (2)	3.1831 (13)	173.(2)
N4—H5···Cl1iv	0.85 (1)	2.45 (1)	3.2805 (13)	166.(2)
N4—H6···O1i	0.87 (1)	2.11 (2)	2.8310 (16)	141.(2)
N3—H4···O1i	0.87 (1)	1.88 (2)	2.6806 (15)	151.(2)
N2—H3···O2	0.88 (1)	2.05 (1)	2.9151 (17)	167.(2)
N2—H2···Cl1	0.87 (1)	2.38 (2)	3.2112 (13)	161.(2)
N1—H1···O2v	0.85 (1)	1.93 (1)	2.7727 (16)	174.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H8⋯O3	0.82 (2)	1.97 (2)	2.7503 (17)	161 (2)
O2—H9⋯Cl1i	0.81 (2)	2.51 (2)	3.2802 (11)	159 (2)
O3—H10⋯Cl1ii	0.83 (2)	2.39 (2)	3.2158 (12)	173 (2)
O3—H11⋯Cl1iii	0.84 (2)	2.35 (2)	3.1831 (13)	173 (2)
N4—H5⋯Cl1iv	0.85 (1)	2.45 (1)	3.2805 (13)	166 (2)
N4—H6⋯O1i	0.87 (1)	2.11 (2)	2.8310 (16)	141 (2)
N3—H4⋯O1i	0.87 (1)	1.88 (2)	2.6806 (15)	151 (2)
N2—H3⋯O2	0.88 (1)	2.05 (1)	2.9151 (17)	167 (2)
N2—H2⋯Cl1	0.87 (1)	2.38 (2)	3.2112 (13)	161 (2)
N1—H1⋯O2v	0.85 (1)	1.93 (1)	2.7727 (16)	174 (2)

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