5-Amino-3-carb­oxy-1H-1,2,4-triazol-4-ium nitrate monohydrate

Fadila Berrah; Rafika Bouchene; Sofiane Bouacida; Thierry Roisnel

doi:10.1107/S1600536812011154

. 2012 Mar 21;68(Pt 4):o1116. doi: 10.1107/S1600536812011154

5-Amino-3-carboxy-1H-1,2,4-triazol-4-ium nitrate monohydrate

Fadila Berrah ^a,^*,^‡, Rafika Bouchene ^a,^‡, Sofiane Bouacida ^b,^‡, Thierry Roisnel ^c

PMCID: PMC3344063 PMID: 22589972

Abstract

The two-dimensional crystal packing of the title compound, C₃H₅N₄O₂ ⁺·NO₂ ⁻·H₂O, results from the stacking of well separated layers (i.e. with nothing between the layers) parallel to the (-113) plane in which adjacent cations adopt a head-to-head arrangement such that two –COOH groups are linked via two water molecules (the water O atom behaves simultaneously as donor and acceptor of hydrogen bonds) and two –NH₂ groups are linked through two nitrate anions. This arrangement leads to alternating hydrophilic and hydrophobic zones in which O—H⋯O and N—H⋯O hydrogen bonds, respectively, are observed.

Related literature

For properties of 1,2,4-triazoles, see: Ouakkaf et al. (2011 ▶). For related structures, see: Fernandes et al. (2011 ▶); Berrah et al. (2011a ▶,b ▶); Jebas et al. (2006 ▶).

Experimental

Crystal data

C₃H₅N₄O₂ ⁺·NO₃ ⁻·H₂O
M _r = 209.14
Triclinic,
a = 4.9934 (13) Å
b = 6.7454 (17) Å
c = 12.446 (3) Å
α = 97.572 (12)°
β = 100.524 (13)°
γ = 98.933 (13)°
V = 401.60 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 150 K
0.42 × 0.2 × 0.11 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.863, T _max = 0.982
4012 measured reflections
1821 independent reflections
1563 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.109
S = 1.03
1821 reflections
134 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011154/pv2522sup1.cif

e-68-o1116-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011154/pv2522Isup2.hkl

e-68-o1116-Isup2.hkl^{(87.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011154/pv2522Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1W	0.82	1.72	2.5210 (17)	166
O1W—H2W⋯O4ⁱ	0.84 (3)	1.97 (3)	2.7985 (18)	166 (2)
O1W—H1W⋯N3ⁱⁱ	0.86 (2)	2.05 (3)	2.9011 (19)	172 (2)
N5—H5B⋯O2ⁱⁱⁱ	0.86	2.04	2.8352 (18)	154
N2—H2⋯O1ⁱⁱⁱ	0.86	2.02	2.8790 (17)	178
N4—H4⋯O1	0.86	2.06	2.9112 (18)	171

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

Acknowledgments

We are grateful to the LCATM laboratory, Université Larbi Ben M’Hidi, Oum El Bouaghi, Algeria, for financial support.

supplementary crystallographic information

Comment

Following our on-going interest on crystal structures of hybrid compounds established by hydrogen bonds and in attempts to clarify anion substitution influence upon hydrogen bonding patterns, we have undertaken synthesis of new compounds using 1,2,4-triazol derivatives and various inorganic acids (Ouakkaf et al., 2011). In this article, we report the preparations and crystal structure of the title compound.

The asymmetric unit of the title compound contains a cation, an anion and a water molecule linked by O—H···O and N—H···O hydrogen bonds (Fig.1.) The geometry of the triazole planar ring is similar to that seen in related compounds (Fernandes et al., 2011; Ouakkaf et al., 2011); it exhibits a short distance of 1.3023 (19) Å showing the double-bond formed between atoms C2 and N3, two intermediat bonds (1.3443 (18) and 1.3529 (19) Å) associated with a delocalized double bond (N4 ≐C3 ≐N2), and two long distances 1.3698 (19) and 1.3779 (18) Å related to the single bonds C2—N2 and N3—N4, respectively.

The two-dimensional network of the title compound results from the stacking of well separated planar layers parallel to (-113) plane (Fig. 2); analogous networks have been observed in other nitrate compounds (Berrah et al., 2011a,b; Jebas et al., 2006). In each layer, the adjacent cations are oriented in a head to head configuration in such a manner that two –COOH groups are linked via two water molecules (H₂O behaves simultaneously as donor and acceptor of hydrogen bonds) and two –NH₂groups are linked through two nitrate anions (Fig. 3 and Table 1). This arrangement leads to an alternating hydrophilic and hydrophobic zones where O—H···O and N—H···O H-bonds are observed, respectively.

Experimental

Colourless crystals of the title compound were grown by slow evaporation of water-methanol (1:1) solution of 5-amino-1,2,4-triazol-1H-3-carboxylic acid hydrate and nitric acid in a 1:1 stoichiometric ratio.