5-Amino-1H-1,2,4-triazol-4-ium hydrogen oxalate.

In the title salt, C2H5N4 (+)·C2HO4 (-), the hydrogen oxalate anions form corrugated chains parallel to the c axis, linked by inter-molecular O-H⋯O hydrogen bonds. The 5-amino-1H-1,2,4-triazol-4-ium cations are connected into centrosymmetric clusters via weak C-H⋯N hydrogen bonds forming nine-membered rings with an R 3 (3)(9) motif. These clusters are inter-connected via anions through N-H⋯O hydrogen bonds, building a three-dimensional network.

Related literature

For the properties of triazoles, see: Li et al. (2004 ▶); Mernari et al. (1998 ▶); Bentiss et al. (1999 ▶). For graph-set notation of hydrogen bonding, see: Bernstein et al. (1995 ▶). For related structures, see: Matulková et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C2H5N4 +·C2HO4 −

M = 174.13

Trigonal,

a = 23.093 (4) Å

c = 6.603 (3) Å

V = 3049.3 (16) Å3

Z = 18

Ag Kα radiation

λ = 0.56080 Å

μ = 0.09 mm−1

T = 293 K

0.35 × 0.3 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3909 measured reflections

3313 independent reflections

1929 reflections with I > 2σ(I)

R int = 0.023

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.194

S = 1.04

3313 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019363/pv2640sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019363/pv2640Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019363/pv2640Isup3.cml

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

C2H5N4+·C2HO4−	Dx = 1.707 Mg m−3
Mr = 174.13	Ag Kα radiation, λ = 0.56080 Å
Trigonal, R3	Cell parameters from 25 reflections
Hall symbol: -R 3	θ = 9–11°
a = 23.093 (4) Å	µ = 0.09 mm−1
c = 6.603 (3) Å	T = 293 K
V = 3049.3 (16) Å3	Prism, colorless
Z = 18	0.35 × 0.3 × 0.25 mm
F(000) = 1620

Enraf–Nonius CAD-4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.4°
Graphite monochromator	h = −1→33
non–profiled ω scans	k = −1→33
3909 measured reflections	l = −11→11
3313 independent reflections	2 standard reflections every 120 min
1929 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0979P)2 + 1.6007P] where P = (Fo2 + 2Fc2)/3
3313 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.50 e Å−3
0 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
O1	0.35441 (6)	−0.03841 (6)	0.4263 (2)	0.0279 (3)
O4	0.50310 (6)	−0.02945 (6)	0.2759 (2)	0.0304 (3)
O3	0.46709 (6)	0.04345 (6)	0.2350 (2)	0.0268 (3)
O2	0.37748 (7)	−0.12148 (6)	0.4035 (3)	0.0384 (4)
N3	0.40979 (7)	−0.14645 (7)	−0.1112 (2)	0.0282 (3)
H5	0.4515	−0.1183	−0.1295	0.034*
N1	0.36951 (8)	−0.06980 (8)	−0.0972 (3)	0.0310 (3)
N2	0.30499 (7)	−0.18848 (8)	−0.0659 (3)	0.0308 (3)
H4	0.2661	−0.1927	−0.0501	0.037*
C3	0.36142 (7)	−0.13134 (8)	−0.0947 (2)	0.0228 (3)
C2	0.46067 (7)	−0.01195 (7)	0.2875 (2)	0.0205 (3)
C4	0.31868 (9)	−0.23999 (9)	−0.0656 (3)	0.0338 (4)
H6	0.2877	−0.2851	−0.0480	0.041*
C1	0.39246 (8)	−0.06374 (7)	0.3785 (2)	0.0217 (3)
N4	0.38176 (9)	−0.21484 (9)	−0.0939 (3)	0.0429 (4)
H1	0.3155 (15)	−0.0699 (15)	0.467 (4)	0.054 (8)*
H3	0.4074 (14)	−0.0368 (14)	−0.142 (4)	0.049 (7)*
H2	0.3342 (14)	−0.0667 (12)	−0.113 (4)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0205 (5)	0.0209 (5)	0.0446 (7)	0.0121 (4)	0.0104 (5)	0.0068 (5)
O4	0.0229 (5)	0.0301 (6)	0.0442 (7)	0.0179 (5)	0.0058 (5)	0.0057 (5)
O3	0.0183 (5)	0.0208 (5)	0.0405 (7)	0.0091 (4)	0.0014 (5)	0.0076 (5)
O2	0.0334 (7)	0.0216 (6)	0.0648 (10)	0.0172 (5)	0.0158 (6)	0.0122 (6)
N3	0.0185 (6)	0.0235 (6)	0.0423 (8)	0.0103 (5)	0.0040 (5)	0.0025 (6)
N1	0.0276 (7)	0.0244 (7)	0.0437 (9)	0.0149 (6)	−0.0001 (6)	0.0016 (6)
N2	0.0159 (5)	0.0274 (7)	0.0448 (9)	0.0076 (5)	0.0030 (5)	0.0023 (6)
C3	0.0170 (6)	0.0235 (7)	0.0270 (7)	0.0093 (5)	0.0004 (5)	−0.0004 (5)
C2	0.0177 (6)	0.0206 (6)	0.0237 (7)	0.0101 (5)	0.0000 (5)	0.0008 (5)
C4	0.0219 (7)	0.0183 (7)	0.0541 (12)	0.0047 (6)	0.0015 (7)	0.0026 (7)
C1	0.0203 (6)	0.0195 (6)	0.0279 (7)	0.0120 (5)	0.0022 (5)	0.0037 (5)
N4	0.0336 (9)	0.0314 (8)	0.0665 (12)	0.0184 (7)	0.0035 (8)	0.0027 (8)

O1—C1	1.3143 (19)	N1—H3	0.88 (3)
O1—H1	0.87 (3)	N1—H2	0.86 (3)
O4—C2	1.2351 (19)	N2—C3	1.325 (2)
O3—C2	1.2607 (18)	N2—C4	1.375 (2)
O2—C1	1.2099 (19)	N2—H4	0.8600
N3—C3	1.331 (2)	C2—C1	1.546 (2)
N3—N4	1.380 (2)	C4—N4	1.284 (3)
N3—H5	0.8600	C4—H6	0.9300
N1—C3	1.338 (2)
C1—O1—H1	110.1 (19)	N3—C3—N1	126.00 (15)
C3—N3—N4	108.56 (14)	O4—C2—O3	127.23 (15)
C3—N3—H5	125.7	O4—C2—C1	116.06 (13)
N4—N3—H5	125.7	O3—C2—C1	116.71 (13)
C3—N1—H3	118.4 (19)	N4—C4—N2	107.94 (15)
C3—N1—H2	117.1 (17)	N4—C4—H6	126.0
H3—N1—H2	118 (2)	N2—C4—H6	126.0
C3—N2—C4	108.94 (14)	O2—C1—O1	124.85 (15)
C3—N2—H4	125.5	O2—C1—C2	121.67 (14)
C4—N2—H4	125.5	O1—C1—C2	113.47 (12)
N2—C3—N3	106.69 (14)	C4—N4—N3	107.86 (15)
N2—C3—N1	127.24 (15)
C4—N2—C3—N3	−0.3 (2)	O3—C2—C1—O2	168.06 (17)
C4—N2—C3—N1	−177.35 (19)	O4—C2—C1—O1	166.66 (15)
N4—N3—C3—N2	0.6 (2)	O3—C2—C1—O1	−12.8 (2)
N4—N3—C3—N1	177.71 (18)	N2—C4—N4—N3	0.5 (2)
C3—N2—C4—N4	−0.1 (2)	C3—N3—N4—C4	−0.7 (2)
O4—C2—C1—O2	−12.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.87 (3)	1.72 (3)	2.5845 (17)	174 (3)
N1—H2···O1ii	0.86 (3)	2.29 (3)	3.087 (2)	155 (2)
N1—H3···O4iii	0.88 (3)	2.06 (3)	2.925 (2)	171 (3)
N2—H4···O4iv	0.86	2.09	2.892 (2)	154
N2—H4···O2iv	0.86	2.28	2.878 (2)	127
N3—H5···O3iii	0.86	1.94	2.7652 (18)	161
C4—H6···N4v	0.93	2.41	3.313 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.87 (3)	1.72 (3)	2.5845 (17)	174 (3)
N1—H2⋯O1ii	0.86 (3)	2.29 (3)	3.087 (2)	155 (2)
N1—H3⋯O4iii	0.88 (3)	2.06 (3)	2.925 (2)	171 (3)
N2—H4⋯O4iv	0.86	2.09	2.892 (2)	154
N2—H4⋯O2iv	0.86	2.28	2.878 (2)	127
N3—H5⋯O3iii	0.86	1.94	2.7652 (18)	161
C4—H6⋯N4v	0.93	2.41	3.313 (3)	165

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