2-Amino-pyrimidinium hydrogen sulfate.

In the crystal structure of the title compound, C(4)H(6)N(3) (+)·HSO(4) (-), hydrogen sulfate anions self-assemble through O-H⋯O hydrogen bonds, forming chains along the b axis, while the cations form centrosymmetric pairs via N-H⋯N hydrogen bonds. The 2-amino-pyrimidinium pairs are linked to the sulfate anions via N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (10[Formula: see text]). In addition, weak inter-molecular C-H⋯O contacts generate a three-dimensional network.

Related literature

For the biological properties of pyrimidines, see: Rabie et al. (2007 ▶); Rival et al. (1991 ▶). For applications of amino­pyrimidines, see: Rospenk & Koll (2007 ▶). For amino­pyrimidine salts, see: Hemamalini et al. (2005 ▶); Childs et al. (2007 ▶); Lee et al. (2003 ▶); Ye et al. (2002 ▶). For sulfate salts with organic cations, see: Xu et al. (2009a ▶,b ▶).

Experimental

Crystal data

C4H6N3 +·HSO4 −

M = 193.19

Monoclinic,

a = 8.388 (2) Å

b = 5.208 (3) Å

c = 18.468 (4) Å

β = 112.84 (2)°

V = 743.6 (5) Å3

Z = 4

Ag Kα radiation

λ = 0.56087 Å

μ = 0.22 mm−1

T = 293 K

0.25 × 0.21 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3738 measured reflections

3647 independent reflections

2520 reflections with I > 2σ(I)

R int = 0.015

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 1.07

3647 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.71 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: ORTEPIII (Burnett & Johnson, 1996 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011123/lh5222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011123/lh5222Isup2.hkl

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

C4H6N3+·HSO4−	F(000) = 400
Mr = 193.19	Dx = 1.726 Mg m−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56087 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.388 (2) Å	θ = 9–11°
b = 5.208 (3) Å	µ = 0.22 mm−1
c = 18.468 (4) Å	T = 293 K
β = 112.84 (2)°	Prism, colorless
V = 743.6 (5) Å3	0.25 × 0.21 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.015
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.1°
graphite	h = −14→13
non–profiled ω scans	k = −8→0
3738 measured reflections	l = −30→13
3647 independent reflections	2 standard reflections every 120 min
2520 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.0037P] where P = (Fo2 + 2Fc2)/3
3647 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.71 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
S	0.67465 (5)	−0.13645 (8)	0.21545 (2)	0.02768 (11)
O1	0.66596 (17)	−0.4361 (3)	0.22175 (9)	0.0400 (3)
H1	0.5717	−0.4774	0.2218	0.060*
O2	0.5491 (2)	−0.0595 (3)	0.14085 (8)	0.0515 (4)
O3	0.85241 (16)	−0.0898 (3)	0.22478 (7)	0.0365 (3)
O4	0.64241 (17)	−0.0315 (3)	0.28174 (8)	0.0408 (3)
N1	0.9071 (2)	0.3742 (3)	0.39016 (9)	0.0430 (4)
H1A	0.8905	0.4952	0.4181	0.052*
H1B	0.8390	0.3583	0.3416	0.052*
N2	1.06403 (19)	0.0245 (3)	0.37781 (8)	0.0319 (3)
H2	0.9966	0.0117	0.3291	0.038*
N3	1.1419 (2)	0.2419 (3)	0.49787 (8)	0.0358 (3)
C1	1.0366 (2)	0.2136 (3)	0.42160 (9)	0.0295 (3)
C2	1.1941 (2)	−0.1444 (3)	0.40855 (11)	0.0376 (3)
H2A	1.2105	−0.2737	0.3774	0.045*
C3	1.3011 (3)	−0.1248 (4)	0.48528 (12)	0.0429 (4)
H3	1.3912	−0.2404	0.5085	0.051*
C4	1.2703 (3)	0.0753 (4)	0.52752 (10)	0.0418 (4)
H4	1.3442	0.0939	0.5799	0.050*

	U11	U22	U33	U12	U13	U23
S	0.03166 (18)	0.02383 (17)	0.02574 (16)	−0.00177 (13)	0.00914 (13)	−0.00139 (13)
O1	0.0418 (7)	0.0245 (5)	0.0581 (8)	−0.0021 (5)	0.0240 (6)	−0.0020 (5)
O2	0.0539 (9)	0.0493 (9)	0.0337 (6)	−0.0035 (7)	−0.0023 (6)	0.0068 (6)
O3	0.0380 (6)	0.0388 (7)	0.0365 (6)	−0.0084 (5)	0.0186 (5)	−0.0057 (5)
O4	0.0423 (7)	0.0420 (7)	0.0409 (6)	0.0016 (5)	0.0192 (5)	−0.0115 (5)
N1	0.0456 (8)	0.0428 (9)	0.0325 (7)	0.0091 (7)	0.0062 (6)	−0.0061 (6)
N2	0.0408 (7)	0.0292 (6)	0.0263 (5)	−0.0040 (5)	0.0135 (5)	−0.0039 (5)
N3	0.0420 (7)	0.0361 (8)	0.0250 (6)	−0.0001 (6)	0.0084 (5)	−0.0043 (5)
C1	0.0361 (7)	0.0266 (6)	0.0255 (6)	−0.0042 (6)	0.0116 (5)	−0.0025 (5)
C2	0.0461 (9)	0.0287 (7)	0.0438 (9)	−0.0005 (7)	0.0238 (8)	−0.0030 (7)
C3	0.0450 (9)	0.0396 (10)	0.0436 (9)	0.0093 (8)	0.0168 (8)	0.0075 (8)
C4	0.0439 (9)	0.0468 (10)	0.0289 (7)	0.0016 (8)	0.0078 (7)	0.0022 (7)

S—O2	1.4288 (14)	N2—C1	1.350 (2)
S—O3	1.4535 (13)	N2—H2	0.8600
S—O4	1.4588 (13)	N3—C4	1.324 (3)
S—O1	1.5690 (17)	N3—C1	1.349 (2)
O1—H1	0.8200	C2—C3	1.355 (3)
N1—C1	1.314 (2)	C2—H2A	0.9300
N1—H1A	0.8600	C3—C4	1.385 (3)
N1—H1B	0.8600	C3—H3	0.9300
N2—C2	1.343 (2)	C4—H4	0.9300
O2—S—O3	113.94 (9)	C4—N3—C1	117.25 (16)
O2—S—O4	113.37 (10)	N1—C1—N3	119.05 (16)
O3—S—O4	110.72 (8)	N1—C1—N2	120.26 (15)
O2—S—O1	108.21 (9)	N3—C1—N2	120.69 (16)
O3—S—O1	103.46 (8)	N2—C2—C3	119.50 (17)
O4—S—O1	106.34 (9)	N2—C2—H2A	120.3
S—O1—H1	109.5	C3—C2—H2A	120.3
C1—N1—H1A	120.0	C2—C3—C4	116.90 (18)
C1—N1—H1B	120.0	C2—C3—H3	121.5
H1A—N1—H1B	120.0	C4—C3—H3	121.5
C2—N2—C1	121.60 (15)	N3—C4—C3	124.04 (17)
C2—N2—H2	119.2	N3—C4—H4	118.0
C1—N2—H2	119.2	C3—C4—H4	118.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.79	2.6100 (19)	174
N1—H1B···O1ii	0.86	2.38	3.140 (2)	148
N1—H1B···O4	0.86	2.58	3.155 (2)	125
N1—H1A···N3iii	0.86	2.16	3.017 (2)	172
N2—H2···O3	0.86	1.91	2.756 (2)	168
C2—H2A···O3iv	0.93	2.40	3.294 (2)	160
C3—H3···O2v	0.93	2.51	3.262 (3)	138
C4—H4···O4vi	0.93	2.53	3.316 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.79	2.6100 (19)	174
N1—H1B⋯O1ii	0.86	2.38	3.140 (2)	148
N1—H1B⋯O4	0.86	2.58	3.155 (2)	125
N1—H1A⋯N3iii	0.86	2.16	3.017 (2)	172
N2—H2⋯O3	0.86	1.91	2.756 (2)	168
C2—H2A⋯O3iv	0.93	2.40	3.294 (2)	160
C3—H3⋯O2v	0.93	2.51	3.262 (3)	138
C4—H4⋯O4vi	0.93	2.53	3.316 (2)	142

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