2-Amino-pyrimidinium hydrogen chloranilate monohydrate.

In the title compound, C(4)H(6)N(3) (+)·C(6)HCl(2)O(4) (-)·H(2)O, anions, cations and water mol-ecules are linked by inter-molecular O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds into one-dimensional tapes along [111]. These tapes are further linked by weak Cl⋯Cl inter-actions [Cl⋯Cl = 3.394 (2) Å], forming sheets parallel to the (10) plane.

Related literature

For background information, see: Aakeröy & Salmon (2005 ▶); Aakeröy et al. (2007 ▶); Abrahams et al. (2002 ▶); Cueto et al. (1992 ▶); Kawata et al. (1994 ▶, 1998 ▶). For related crystal structures, see: Meng & Qian (2006 ▶); Min et al. (2006 ▶, 2007 ▶); Murata et al. (2007 ▶); Wang & Wei (2005 ▶); Yang (2007 ▶); Gaballa et al. (2008 ▶); Gotoh et al. (2006 ▶, 2007a ▶,b ▶,c ▶); Jia et al. (2008 ▶). For bond-length data, see: Allen (2002 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C4H6N3 +·C6HCl2O4 −·H2O

M = 322.10

Triclinic,

a = 6.7969 (5) Å

b = 9.4631 (6) Å

c = 11.0604 (7) Å

α = 106.074 (1)°

β = 105.892 (1)°

γ = 101.925 (1)°

V = 626.01 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 292 (2) K

0.27 × 0.10 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.979

5691 measured reflections

2121 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.197

S = 0.97

2121 reflections

199 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034740/lh2716sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034740/lh2716Isup2.hkl

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

C4H6N3+·C6HCl2O4−·H2O	Z = 2
Mr = 322.10	F(000) = 328
Triclinic, P1	Dx = 1.709 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7969 (5) Å	Cell parameters from 1004 reflections
b = 9.4631 (6) Å	θ = 2.2–25.2°
c = 11.0604 (7) Å	µ = 0.54 mm−1
α = 106.074 (1)°	T = 292 K
β = 105.892 (1)°	Plate, red
γ = 101.925 (1)°	0.27 × 0.10 × 0.04 mm
V = 626.01 (7) Å3

Bruker SMART APEX CCD area-detector diffractometer	2121 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1348 reflections with I > 2σ(I)
graphite	Rint = 0.071
0.3° wide ω exposures scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.857, Tmax = 0.979	k = −11→11
5691 measured reflections	l = −13→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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.1114P)2] where P = (Fo2 + 2Fc2)/3
2121 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.66 e Å−3
6 restraints	Δρmin = −0.45 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.1247 (7)	0.1172 (6)	0.1769 (5)	0.0361 (12)
C2	−0.1473 (7)	−0.0408 (6)	0.2001 (5)	0.0425 (13)
C3	−0.2335 (8)	−0.1755 (5)	0.0838 (5)	0.0378 (12)
C4	−0.3014 (7)	−0.1738 (6)	−0.0449 (5)	0.0358 (12)
C5	−0.2867 (7)	−0.0171 (6)	−0.0623 (5)	0.0372 (12)
C6	−0.2029 (7)	0.1163 (6)	0.0438 (5)	0.0363 (12)
Cl1	−0.1870 (2)	0.29304 (15)	0.02393 (13)	0.0479 (5)
Cl2	−0.2558 (2)	−0.35198 (15)	0.10632 (14)	0.0500 (5)
O1	−0.0385 (6)	0.2339 (4)	0.2793 (3)	0.0506 (10)
O2	−0.0871 (6)	−0.0336 (4)	0.3183 (3)	0.0547 (11)
O3	−0.3780 (6)	−0.2884 (4)	−0.1520 (4)	0.0513 (10)
O4	−0.3561 (6)	−0.0196 (4)	−0.1857 (4)	0.0509 (10)
H4	−0.399 (10)	−0.110 (3)	−0.238 (5)	0.076*
C7	0.3286 (7)	0.6009 (6)	0.5065 (5)	0.0365 (12)
C8	0.5278 (8)	0.8089 (6)	0.4821 (6)	0.0462 (14)
H8	0.6301	0.9059	0.5206	0.055*
C9	0.4403 (9)	0.7485 (6)	0.3461 (6)	0.0481 (14)
H9	0.4801	0.8020	0.2933	0.058*
C10	0.2900 (8)	0.6044 (7)	0.2895 (5)	0.0468 (14)
H10	0.2244	0.5573	0.1967	0.056*
N1	0.4796 (6)	0.7413 (5)	0.5644 (4)	0.0447 (11)
N2	0.2407 (6)	0.5338 (5)	0.3717 (4)	0.0378 (11)
H2	0.162 (9)	0.442 (6)	0.329 (5)	0.045*
N3	0.2768 (7)	0.5294 (6)	0.5858 (5)	0.0504 (12)
H3A	0.200 (8)	0.434 (3)	0.548 (5)	0.060*
H3B	0.337 (9)	0.579 (6)	0.671 (2)	0.060*
O5	0.0043 (6)	0.2393 (4)	0.5451 (3)	0.0493 (10)
H5A	−0.050 (10)	0.171 (5)	0.468 (2)	0.074*
H5B	0.021 (10)	0.205 (6)	0.606 (3)	0.074*

	U11	U22	U33	U12	U13	U23
C1	0.026 (3)	0.037 (3)	0.041 (3)	0.006 (2)	0.012 (2)	0.009 (3)
C2	0.024 (3)	0.053 (4)	0.050 (3)	0.008 (2)	0.011 (2)	0.023 (3)
C3	0.034 (3)	0.034 (3)	0.046 (3)	0.013 (2)	0.015 (2)	0.013 (3)
C4	0.020 (3)	0.042 (3)	0.040 (3)	0.011 (2)	0.010 (2)	0.006 (3)
C5	0.027 (3)	0.047 (3)	0.042 (3)	0.016 (2)	0.016 (2)	0.016 (3)
C6	0.023 (3)	0.045 (3)	0.048 (3)	0.015 (2)	0.015 (2)	0.020 (3)
Cl1	0.0427 (8)	0.0484 (9)	0.0582 (9)	0.0174 (6)	0.0181 (7)	0.0246 (7)
Cl2	0.0507 (9)	0.0413 (8)	0.0540 (9)	0.0113 (6)	0.0153 (7)	0.0161 (7)
O1	0.058 (2)	0.044 (2)	0.040 (2)	0.0055 (19)	0.0164 (19)	0.0100 (19)
O2	0.070 (3)	0.049 (2)	0.034 (2)	0.010 (2)	0.0066 (19)	0.0145 (18)
O3	0.052 (2)	0.046 (2)	0.044 (2)	0.0126 (19)	0.0096 (19)	0.0068 (19)
O4	0.062 (3)	0.046 (2)	0.038 (2)	0.016 (2)	0.0110 (19)	0.0117 (17)
C7	0.024 (3)	0.045 (3)	0.043 (3)	0.018 (2)	0.013 (2)	0.012 (3)
C8	0.026 (3)	0.047 (3)	0.059 (4)	0.006 (2)	0.015 (3)	0.013 (3)
C9	0.044 (3)	0.057 (4)	0.053 (4)	0.019 (3)	0.019 (3)	0.029 (3)
C10	0.040 (3)	0.062 (4)	0.043 (3)	0.021 (3)	0.017 (3)	0.017 (3)
N1	0.031 (2)	0.048 (3)	0.051 (3)	0.016 (2)	0.010 (2)	0.011 (2)
N2	0.024 (2)	0.037 (2)	0.044 (3)	0.0089 (18)	0.0065 (19)	0.007 (2)
N3	0.041 (3)	0.052 (3)	0.058 (3)	0.014 (2)	0.017 (3)	0.020 (3)
O5	0.051 (2)	0.059 (2)	0.040 (2)	0.021 (2)	0.013 (2)	0.0214 (19)

C1—O1	1.234 (6)	C7—N2	1.347 (6)
C1—C6	1.419 (7)	C7—N1	1.354 (6)
C1—C2	1.569 (7)	C8—N1	1.321 (6)
C2—O2	1.236 (5)	C8—C9	1.355 (7)
C2—C3	1.412 (7)	C8—H8	0.9300
C3—C4	1.377 (7)	C9—C10	1.377 (7)
C3—Cl2	1.738 (5)	C9—H9	0.9300
C4—O3	1.252 (6)	C10—N2	1.341 (6)
C4—C5	1.533 (7)	C10—H10	0.9300
C5—O4	1.308 (6)	N2—H2	0.84 (5)
C5—C6	1.346 (7)	N3—H3A	0.86 (2)
C6—Cl1	1.732 (5)	N3—H3B	0.86 (2)
O4—H4	0.83 (2)	O5—H5A	0.82 (4)
C7—N3	1.323 (6)	O5—H5B	0.82 (4)
O1—C1—C6	125.3 (5)	N3—C7—N1	118.2 (5)
O1—C1—C2	115.6 (4)	N2—C7—N1	120.6 (4)
C6—C1—C2	119.1 (5)	N1—C8—C9	125.3 (5)
O2—C2—C3	127.1 (5)	N1—C8—H8	117.3
O2—C2—C1	116.4 (5)	C9—C8—H8	117.3
C3—C2—C1	116.5 (4)	C8—C9—C10	117.1 (5)
C4—C3—C2	123.5 (4)	C8—C9—H9	121.4
C4—C3—Cl2	118.9 (4)	C10—C9—H9	121.4
C2—C3—Cl2	117.6 (4)	N2—C10—C9	118.2 (5)
O3—C4—C3	126.8 (5)	N2—C10—H10	120.9
O3—C4—C5	115.2 (4)	C9—C10—H10	120.9
C3—C4—C5	118.1 (5)	C8—N1—C7	116.5 (5)
O4—C5—C6	121.7 (5)	C10—N2—C7	122.2 (5)
O4—C5—C4	116.6 (4)	C10—N2—H2	112 (3)
C6—C5—C4	121.8 (4)	C7—N2—H2	126 (3)
C5—C6—C1	121.0 (5)	C7—N3—H3A	117 (4)
C5—C6—Cl1	121.7 (4)	C7—N3—H3B	117 (4)
C1—C6—Cl1	117.4 (4)	H3A—N3—H3B	126 (5)
C1—O1—H2	135.7 (14)	H3A—O5—H5A	112 (4)
C2—O2—H5A	118.4 (13)	H3A—O5—H5B	126 (4)
C5—O4—H4	109 (4)	H5A—O5—H5B	114 (3)
N3—C7—N2	121.2 (5)
O1—C1—C2—O2	3.6 (7)	O4—C5—C6—Cl1	1.4 (7)
C6—C1—C2—O2	−176.2 (4)	C4—C5—C6—Cl1	−179.9 (3)
O1—C1—C2—C3	−176.3 (4)	O1—C1—C6—C5	177.2 (5)
C6—C1—C2—C3	3.9 (7)	C2—C1—C6—C5	−3.0 (7)
O2—C2—C3—C4	178.5 (5)	O1—C1—C6—Cl1	−3.0 (7)
C1—C2—C3—C4	−1.7 (7)	C2—C1—C6—Cl1	176.8 (3)
O2—C2—C3—Cl2	−1.0 (7)	C6—C1—O1—H2	−38 (2)
C1—C2—C3—Cl2	178.8 (3)	C2—C1—O1—H2	143 (2)
C2—C3—C4—O3	179.6 (5)	C3—C2—O2—H5A	−163 (2)
Cl2—C3—C4—O3	−0.9 (7)	C1—C2—O2—H5A	17 (2)
C2—C3—C4—C5	−1.4 (7)	N1—C8—C9—C10	−0.4 (8)
Cl2—C3—C4—C5	178.1 (3)	C8—C9—C10—N2	−0.1 (8)
O3—C4—C5—O4	0.4 (6)	C9—C8—N1—C7	−0.7 (8)
C3—C4—C5—O4	−178.8 (4)	N3—C7—N1—C8	179.8 (5)
O3—C4—C5—C6	−178.4 (4)	N2—C7—N1—C8	2.4 (7)
C3—C4—C5—C6	2.5 (7)	C9—C10—N2—C7	1.9 (8)
O4—C5—C6—C1	−178.8 (4)	N3—C7—N2—C10	179.6 (5)
C4—C5—C6—C1	−0.1 (7)	N1—C7—N2—C10	−3.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.83 (2)	2.16 (6)	2.651 (5)	118 (5)
O4—H4···N1i	0.83 (2)	2.07 (4)	2.795 (6)	146 (6)
O5—H5A···O2	0.82 (4)	2.09 (3)	2.872 (5)	156 (6)
O5—H5A···O1	0.82 (4)	2.34 (4)	2.859 (5)	121 (4)
O5—H5B···O2ii	0.82 (4)	2.09 (4)	2.830 (5)	150 (5)
N3—H3A···O5	0.86 (2)	2.02 (3)	2.815 (6)	153 (5)
N2—H2···O1	0.84 (5)	1.98 (5)	2.793 (6)	163 (5)
N3—H3B···O3iii	0.86 (2)	2.17 (4)	2.953 (6)	151 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.83 (2)	2.16 (6)	2.651 (5)	118 (5)
O4—H4⋯N1i	0.83 (2)	2.07 (4)	2.795 (6)	146 (6)
O5—H5A⋯O2	0.82 (4)	2.09 (3)	2.872 (5)	156 (6)
O5—H5A⋯O1	0.82 (4)	2.34 (4)	2.859 (5)	121 (4)
O5—H5B⋯O2ii	0.82 (4)	2.09 (4)	2.830 (5)	150 (5)
N3—H3A⋯O5	0.86 (2)	2.02 (3)	2.815 (6)	153 (5)
N2—H2⋯O1	0.84 (5)	1.98 (5)	2.793 (6)	163 (5)
N3—H3B⋯O3iii	0.86 (2)	2.17 (4)	2.953 (6)	151 (5)

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