2-Amino-pyrimidinium hydrogen oxalate monohydrate.

In the title hydrated salt, C(4)H(6)N(3) (+)·C(2)HO(4) (-)·H(2)O, inter-molecular N-H⋯O and O-H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For the biological properties of pyrimidines, see: Rabie et al. (2007 ▶). For the applications of amino­pyrimidines, see: Rospenk & Koll (2007 ▶). For amino­pyrimidine salts, see: Childs et al. (2007 ▶).

Experimental

Crystal data

C4H6N3 +·C2HO4 −·H2O

M = 203.16

Triclinic,

a = 6.295 (2) Å

b = 6.339 (2) Å

c = 11.111 (4) Å

α = 75.045 (6)°

β = 84.302 (6)°

γ = 86.026 (7)°

V = 425.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 120 K

0.35 × 0.15 × 0.07 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: none

3983 measured reflections

1835 independent reflections

1177 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.148

S = 1.02

1835 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039907/xu2606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039907/xu2606Isup2.hkl

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

C4H6N3+·C2HO4−·H2O	Z = 2
Mr = 203.16	F(000) = 212
Triclinic, P1	Dx = 1.585 Mg m−3
Hall symbol: -P 1	Melting point: 300 K
a = 6.295 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.339 (2) Å	Cell parameters from 851 reflections
c = 11.111 (4) Å	θ = 3.3–27.7°
α = 75.045 (6)°	µ = 0.14 mm−1
β = 84.302 (6)°	T = 120 K
γ = 86.026 (7)°	Prism, colorless
V = 425.8 (2) Å3	0.35 × 0.15 × 0.07 mm

Bruker SMART 1000 CCD area-detector diffractometer	1177 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.030
graphite	θmax = 27.0°, θmin = 1.9°
φ and ω scans	h = −8→8
3983 measured reflections	k = −8→8
1835 independent reflections	l = −14→14

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)] = 0.055	Hydrogen site location: mixed
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.047P)2 + 0.72P] where P = (Fo2 + 2Fc2)/3
1835 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.29 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
N1	0.2235 (4)	0.3419 (4)	0.6301 (2)	0.0225 (5)
H1	0.235 (5)	0.290 (5)	0.559 (3)	0.037 (9)*
N2	0.2566 (4)	0.6890 (4)	0.5036 (2)	0.0263 (6)
H2A	0.270 (5)	0.637 (5)	0.429 (3)	0.027 (8)*
H2B	0.258 (5)	0.836 (6)	0.492 (3)	0.040 (9)*
N3	0.2128 (4)	0.6436 (4)	0.7189 (2)	0.0249 (5)
C2	0.2305 (4)	0.5594 (4)	0.6174 (2)	0.0232 (6)
C4	0.1869 (4)	0.5030 (5)	0.8289 (3)	0.0264 (6)
H4A	0.1759	0.5588	0.9010	0.032*
C5	0.1746 (5)	0.2770 (5)	0.8472 (3)	0.0270 (6)
H5A	0.1530	0.1818	0.9284	0.032*
C6	0.1952 (4)	0.2013 (5)	0.7428 (3)	0.0262 (6)
H6A	0.1895	0.0492	0.7495	0.031*
O1	0.2756 (3)	0.4892 (3)	0.30262 (17)	0.0276 (5)
O2	0.2664 (3)	0.1595 (3)	0.43700 (17)	0.0268 (5)
O3	0.3456 (3)	0.2958 (3)	0.11122 (17)	0.0316 (5)
O4	0.3088 (4)	−0.0288 (3)	0.24753 (19)	0.0323 (5)
H4O	0.314 (5)	−0.099 (6)	0.187 (3)	0.039 (9)*
C7	0.2830 (4)	0.2859 (4)	0.3300 (2)	0.0229 (6)
C8	0.3161 (4)	0.1829 (4)	0.2173 (2)	0.0230 (6)
O1W	0.3244 (4)	0.7844 (3)	0.0656 (2)	0.0298 (5)
H1WA	0.460 (8)	0.772 (7)	0.018 (4)	0.078 (15)*
H1WB	0.306 (7)	0.661 (8)	0.109 (4)	0.070 (14)*

	U11	U22	U33	U12	U13	U23
N1	0.0308 (13)	0.0209 (12)	0.0172 (12)	−0.0009 (9)	−0.0015 (9)	−0.0078 (10)
N2	0.0432 (15)	0.0175 (12)	0.0176 (12)	−0.0027 (10)	−0.0019 (10)	−0.0035 (10)
N3	0.0325 (13)	0.0240 (12)	0.0193 (12)	−0.0007 (10)	−0.0031 (9)	−0.0071 (10)
C2	0.0284 (15)	0.0221 (14)	0.0205 (13)	−0.0005 (11)	−0.0036 (11)	−0.0078 (11)
C4	0.0299 (15)	0.0321 (16)	0.0192 (14)	−0.0013 (12)	−0.0026 (11)	−0.0100 (12)
C5	0.0320 (16)	0.0273 (15)	0.0191 (14)	−0.0006 (12)	−0.0038 (11)	−0.0008 (11)
C6	0.0316 (16)	0.0211 (13)	0.0244 (14)	−0.0023 (11)	−0.0026 (11)	−0.0028 (11)
O1	0.0423 (12)	0.0178 (10)	0.0224 (10)	−0.0008 (8)	−0.0025 (8)	−0.0050 (8)
O2	0.0458 (12)	0.0174 (9)	0.0166 (10)	−0.0010 (8)	−0.0031 (8)	−0.0029 (8)
O3	0.0544 (14)	0.0221 (10)	0.0175 (10)	−0.0041 (9)	−0.0013 (9)	−0.0038 (8)
O4	0.0605 (15)	0.0183 (10)	0.0196 (10)	−0.0015 (9)	−0.0015 (9)	−0.0080 (8)
C7	0.0268 (15)	0.0228 (14)	0.0195 (13)	0.0003 (11)	−0.0016 (11)	−0.0068 (11)
C8	0.0296 (15)	0.0195 (13)	0.0208 (14)	−0.0010 (11)	−0.0022 (11)	−0.0065 (11)
O1W	0.0455 (14)	0.0198 (11)	0.0240 (11)	−0.0019 (9)	−0.0029 (9)	−0.0054 (9)

N1—C6	1.340 (3)	C5—H5A	0.9500
N1—C2	1.353 (3)	C6—H6A	0.9500
N1—H1	0.93 (4)	O1—C7	1.244 (3)
N2—C2	1.320 (3)	O2—C7	1.250 (3)
N2—H2A	0.96 (3)	O3—C8	1.215 (3)
N2—H2B	0.91 (4)	O4—C8	1.299 (3)
N3—C4	1.316 (4)	O4—H4O	0.90 (4)
N3—C2	1.359 (3)	C7—C8	1.545 (4)
C4—C5	1.400 (4)	O1W—H1WA	0.97 (5)
C4—H4A	0.9500	O1W—H1WB	0.82 (5)
C5—C6	1.358 (4)
C6—N1—C2	121.5 (2)	C6—C5—H5A	121.8
C6—N1—H1	119 (2)	C4—C5—H5A	121.8
C2—N1—H1	119 (2)	N1—C6—C5	119.7 (3)
C2—N2—H2A	123.4 (18)	N1—C6—H6A	120.1
C2—N2—H2B	120 (2)	C5—C6—H6A	120.1
H2A—N2—H2B	116 (3)	C8—O4—H4O	119 (2)
C4—N3—C2	116.5 (2)	O1—C7—O2	127.2 (3)
N2—C2—N1	118.4 (2)	O1—C7—C8	115.1 (2)
N2—C2—N3	120.5 (2)	O2—C7—C8	117.7 (2)
N1—C2—N3	121.2 (2)	O3—C8—O4	124.8 (3)
N3—C4—C5	124.7 (3)	O3—C8—C7	121.1 (2)
N3—C4—H4A	117.7	O4—C8—C7	114.1 (2)
C5—C4—H4A	117.7	H1WA—O1W—H1WB	104 (4)
C6—C5—C4	116.4 (3)
C6—N1—C2—N2	−179.3 (3)	C2—N1—C6—C5	−0.5 (4)
C6—N1—C2—N3	1.2 (4)	C4—C5—C6—N1	−0.6 (4)
C4—N3—C2—N2	179.9 (3)	O1—C7—C8—O3	4.3 (4)
C4—N3—C2—N1	−0.6 (4)	O2—C7—C8—O3	−175.8 (3)
C2—N3—C4—C5	−0.7 (4)	O1—C7—C8—O4	−175.5 (2)
N3—C4—C5—C6	1.3 (4)	O2—C7—C8—O4	4.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (3)	1.75 (3)	2.671 (3)	173 (3)
N2—H2A···O1	0.96 (3)	1.87 (3)	2.827 (3)	170 (3)
N2—H2B···O2i	0.91 (4)	1.99 (4)	2.885 (3)	171 (3)
O4—H4O···O1Wii	0.89 (3)	1.69 (4)	2.584 (3)	176 (4)
O1W—H1WA···O3iii	0.97 (5)	1.91 (5)	2.827 (3)	158 (4)
O1W—H1WB···O1	0.82 (5)	2.14 (4)	2.812 (3)	139 (4)
O1W—H1WB···O3	0.82 (5)	2.31 (5)	3.002 (3)	144 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.93 (3)	1.75 (3)	2.671 (3)	173 (3)
N2—H2A⋯O1	0.96 (3)	1.87 (3)	2.827 (3)	170 (3)
N2—H2B⋯O2i	0.91 (4)	1.99 (4)	2.885 (3)	171 (3)
O4—H4O⋯O1Wii	0.89 (3)	1.69 (4)	2.584 (3)	176 (4)
O1W—H1WA⋯O3iii	0.97 (5)	1.91 (5)	2.827 (3)	158 (4)
O1W—H1WB⋯O1	0.82 (5)	2.14 (4)	2.812 (3)	139 (4)
O1W—H1WB⋯O3	0.82 (5)	2.31 (5)	3.002 (3)	144 (4)

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