2-Amino-pyrimidinium dihydrogen phosphate monohydrate.

In the title compound, C(4)H(6)N(3) (+)·H(2)O(4)P(-)·H(2)O, the pyrimidin-ium ring is essentially planar, with an r.m.s. deviation of 0.0016 Å. In the structure, pairs of symmetry-related anions are connected into centrosymmetric clusters via strong O-H⋯O hydrogen bonds forming six-membered rings with an R(2) (2)(6) motif. These clusters are inter-connected via water mol-ecules through OW-H⋯O hydrogen bonds, building an infinite layer parallel to the ab plane. Moreover, infinite chains of 2-amino-pyrimidinium cations spread along the a-axis direction. These chains are connected to the inorganic layer through N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds, which, together with electrostatic and van der Waals inter-actions, contribute to the cohesion and stability of the network in the crystal structure.

Related literature

For the biological activity of amino­pyrimidinium derivatives, see: Grier et al. (1980 ▶); Gueiffier et al. (1996 ▶); Rival et al. (1991 ▶); Li et al. (2009 ▶). For related structures, see: Cheng et al. (2010 ▶); Narayana et al. (2008 ▶). For graph-set notation of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C4H6N3 +·H2PO4 −·H2O

M = 211.12

Triclinic,

a = 6.212 (3) Å

b = 8.600 (4) Å

c = 9.462 (2) Å

α = 109.56 (3)°

β = 106.38 (2)°

γ = 95.50 (2)°

V = 446.7 (3) Å3

Z = 2

Ag Kα radiation

λ = 0.56083 Å

μ = 0.17 mm−1

T = 293 K

0.40 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

6572 measured reflections

4373 independent reflections

3189 reflections with I > 2σ(I)

R int = 0.018

2 standard reflections every 120 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.03

4373 reflections

158 parameters

3 restraints

All H-atom parameters refined

Δρmax = 0.68 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994) ▶; cell refinement: CAD-4 EXPRESS ▶; data reduction: XCAD4 (Harms & Wocadlo, 1995) ▶; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010658/pv2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010658/pv2399Isup2.hkl

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

C4H6N3+·H2PO4−·H2O	Z = 2
Mr = 211.12	F(000) = 220
Triclinic, P1	Dx = 1.570 Mg m−3
Hall symbol: -P 1	Ag Kα radiation, λ = 0.56083 Å
a = 6.212 (3) Å	Cell parameters from 25 reflections
b = 8.600 (4) Å	θ = 9–11°
c = 9.462 (2) Å	µ = 0.17 mm−1
α = 109.56 (3)°	T = 293 K
β = 106.38 (2)°	Prism, colorless
γ = 95.50 (2)°	0.40 × 0.25 × 0.20 mm
V = 446.7 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.0°
graphite	h = −10→10
non–profiled ω scans	k = −14→14
6572 measured reflections	l = −5→15
4373 independent reflections	2 standard reflections every 120 min
3189 reflections with I > 2σ(I)	intensity decay: 3%

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) = 0.124	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.0087P] where P = (Fo2 + 2Fc2)/3
4373 reflections	(Δ/σ)max = 0.002
158 parameters	Δρmax = 0.68 e Å−3
3 restraints	Δρmin = −0.42 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
P1	0.16874 (4)	0.74641 (3)	1.06016 (4)	0.02665 (8)
O3	0.30367 (14)	0.91480 (10)	1.18597 (11)	0.03404 (18)
O4	−0.07714 (13)	0.70387 (10)	1.05045 (11)	0.03351 (18)
O1	0.30374 (15)	0.61277 (12)	1.09639 (14)	0.0442 (3)
O2	0.16298 (17)	0.73861 (14)	0.89151 (12)	0.0433 (2)
OW	0.56449 (16)	0.79100 (13)	0.85902 (13)	0.0406 (2)
N2	0.15897 (16)	0.12980 (13)	0.39597 (13)	0.03242 (19)
N3	−0.14127 (17)	0.21993 (14)	0.48619 (13)	0.0348 (2)
N1	−0.20502 (17)	−0.03637 (13)	0.28151 (13)	0.0352 (2)
C1	−0.06315 (18)	0.10520 (14)	0.38722 (13)	0.02783 (19)
C2	0.3116 (2)	0.27019 (17)	0.50499 (18)	0.0419 (3)
C4	0.0099 (2)	0.35703 (17)	0.59250 (17)	0.0401 (3)
C3	0.2421 (3)	0.38927 (18)	0.60766 (19)	0.0467 (3)
H1W	0.608 (3)	0.8881 (14)	0.862 (2)	0.052 (5)*
H1	−0.164 (3)	−0.111 (2)	0.218 (2)	0.049 (5)*
H1O	0.232 (4)	0.513 (3)	1.051 (3)	0.075 (7)*
H3	0.201 (3)	0.054 (2)	0.327 (2)	0.049 (5)*
H6	−0.051 (3)	0.439 (2)	0.662 (2)	0.044 (4)*
H5	0.347 (4)	0.487 (3)	0.689 (3)	0.064 (6)*
H2	−0.355 (4)	−0.047 (2)	0.269 (2)	0.053 (5)*
H4	0.455 (4)	0.272 (3)	0.499 (2)	0.060 (6)*
H2W	0.668 (3)	0.761 (2)	0.916 (2)	0.065 (6)*
H2O	0.289 (4)	0.761 (3)	0.883 (3)	0.078 (7)*

	U11	U22	U33	U12	U13	U23
P1	0.01938 (11)	0.02235 (12)	0.03390 (15)	0.00234 (8)	0.00888 (9)	0.00599 (9)
O3	0.0271 (3)	0.0257 (3)	0.0406 (5)	−0.0005 (3)	0.0135 (3)	0.0018 (3)
O4	0.0216 (3)	0.0284 (3)	0.0472 (5)	0.0027 (3)	0.0124 (3)	0.0102 (3)
O1	0.0261 (4)	0.0291 (4)	0.0649 (7)	0.0059 (3)	0.0023 (4)	0.0132 (4)
O2	0.0328 (4)	0.0556 (6)	0.0366 (5)	0.0013 (4)	0.0123 (4)	0.0130 (4)
OW	0.0297 (4)	0.0428 (5)	0.0520 (6)	0.0031 (3)	0.0113 (4)	0.0244 (4)
N2	0.0256 (4)	0.0323 (4)	0.0358 (5)	0.0064 (3)	0.0124 (4)	0.0068 (4)
N3	0.0295 (4)	0.0376 (5)	0.0353 (5)	0.0116 (4)	0.0132 (4)	0.0080 (4)
N1	0.0256 (4)	0.0340 (5)	0.0374 (5)	0.0050 (3)	0.0100 (4)	0.0038 (4)
C1	0.0244 (4)	0.0311 (4)	0.0284 (5)	0.0080 (3)	0.0093 (3)	0.0108 (4)
C2	0.0274 (5)	0.0376 (6)	0.0513 (8)	0.0022 (4)	0.0116 (5)	0.0079 (5)
C4	0.0398 (6)	0.0363 (5)	0.0388 (6)	0.0132 (5)	0.0132 (5)	0.0061 (5)
C3	0.0373 (6)	0.0356 (6)	0.0484 (8)	0.0031 (5)	0.0081 (5)	−0.0006 (5)

P1—O4	1.5055 (11)	N3—C4	1.3207 (18)
P1—O3	1.5056 (12)	N3—C1	1.3473 (15)
P1—O1	1.5583 (11)	N1—C1	1.3194 (16)
P1—O2	1.5645 (11)	N1—H1	0.83 (2)
O1—H1O	0.83 (3)	N1—H2	0.89 (2)
O2—H2O	0.82 (3)	C2—C3	1.354 (2)
OW—H1W	0.843 (9)	C2—H4	0.91 (2)
OW—H2W	0.834 (9)	C4—C3	1.399 (2)
N2—C2	1.3473 (17)	C4—H6	0.98 (2)
N2—C1	1.3503 (15)	C3—H5	0.95 (2)
N2—H3	0.87 (2)
O4—P1—O3	114.86 (5)	C1—N1—H2	118.5 (12)
O4—P1—O1	111.37 (6)	H1—N1—H2	118.3 (17)
O3—P1—O1	106.04 (6)	N1—C1—N3	119.50 (10)
O4—P1—O2	106.56 (6)	N1—C1—N2	118.97 (10)
O3—P1—O2	110.54 (6)	N3—C1—N2	121.51 (10)
O1—P1—O2	107.27 (7)	N2—C2—C3	119.76 (12)
P1—O1—H1O	115.6 (18)	N2—C2—H4	112.8 (13)
P1—O2—H2O	115.0 (18)	C3—C2—H4	127.4 (13)
H1W—OW—H2W	112.2 (18)	N3—C4—C3	124.26 (12)
C2—N2—C1	121.10 (11)	N3—C4—H6	115.4 (10)
C2—N2—H3	120.4 (13)	C3—C4—H6	120.3 (10)
C1—N2—H3	118.5 (13)	C2—C3—C4	116.54 (13)
C4—N3—C1	116.83 (11)	C2—C3—H5	121.6 (14)
C1—N1—H1	122.7 (13)	C4—C3—H5	121.8 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4i	0.83 (3)	1.80 (3)	2.6372 (18)	179 (2)
O2—H2O···OW	0.82 (3)	1.80 (3)	2.6132 (18)	175 (2)
OW—H1W···O3ii	0.84 (1)	1.96 (1)	2.7882 (17)	166 (2)
OW—H2W···O4iii	0.83 (1)	1.95 (1)	2.7843 (16)	177 (2)
N1—H1···O4iv	0.83 (2)	2.08 (2)	2.9070 (18)	177 (2)
N1—H2···O3v	0.89 (2)	2.00 (2)	2.873 (2)	166 (2)
N2—H3···O3iv	0.87 (2)	1.78 (2)	2.6535 (16)	175 (2)
C2—H4···N3iii	0.91 (2)	2.62 (2)	3.513 (2)	169 (2)
C3—H5···OW	0.95 (2)	2.56 (2)	3.477 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4i	0.83 (3)	1.80 (3)	2.6372 (18)	179 (2)
O2—H2O⋯OW	0.82 (3)	1.80 (3)	2.6132 (18)	175 (2)
OW—H1W⋯O3ii	0.84 (1)	1.96 (1)	2.7882 (17)	166 (2)
OW—H2W⋯O4iii	0.83 (1)	1.95 (1)	2.7843 (16)	177 (2)
N1—H1⋯O4iv	0.83 (2)	2.08 (2)	2.9070 (18)	177 (2)
N1—H2⋯O3v	0.89 (2)	2.00 (2)	2.873 (2)	166 (2)
N2—H3⋯O3iv	0.87 (2)	1.78 (2)	2.6535 (16)	175 (2)
C2—H4⋯N3iii	0.91 (2)	2.62 (2)	3.513 (2)	169 (2)
C3—H5⋯OW	0.95 (2)	2.56 (2)	3.477 (2)	164 (2)

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