5-Amino-3-carb-oxy-1H-1,2,4-triazol-4-ium nitrate monohydrate.

The two-dimensional crystal packing of the title compound, C(3)H(5)N(4)O(2) (+)·NO(2) (-)·H(2)O, 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 mol-ecules (the water O atom behaves simultaneously as donor and acceptor of hydrogen bonds) and two -NH(2) groups are linked through two nitrate anions. This arrangement leads to alternating hydro-philic and hydro-phobic 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 = 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

Δρmax = 0.35 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C3H5N4O2+·NO3−·H2O	Z = 2
Mr = 209.14	F(000) = 216
Triclinic, P1	Dx = 1.729 Mg m−3
a = 4.9934 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.7454 (17) Å	Cell parameters from 1584 reflections
c = 12.446 (3) Å	θ = 3.4–27.4°
α = 97.572 (12)°	µ = 0.17 mm−1
β = 100.524 (13)°	T = 150 K
γ = 98.933 (13)°	Stick, colourless
V = 401.60 (18) Å3	0.42 × 0.2 × 0.11 mm

Bruker APEXII diffractometer	1563 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→6
Tmin = 0.863, Tmax = 0.982	k = −6→8
4012 measured reflections	l = −16→15
1821 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.0973P] where P = (Fo2 + 2Fc2)/3
1821 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.35 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
O1	−0.1877 (2)	−0.15602 (16)	0.31865 (9)	0.0218 (3)
N3	−0.0716 (3)	0.32704 (19)	0.20042 (11)	0.0174 (3)
O4	0.2001 (2)	0.80430 (17)	0.13489 (10)	0.0241 (3)
O5	−0.2192 (2)	0.59982 (18)	0.06811 (10)	0.0234 (3)
H5	−0.2505	0.6888	0.0311	0.035*
O1W	−0.3752 (3)	0.82557 (19)	−0.06786 (10)	0.0272 (3)
H2W	−0.319 (5)	0.946 (4)	−0.0762 (18)	0.041*
H1W	−0.544 (5)	0.791 (3)	−0.1043 (19)	0.041*
N5	0.5272 (3)	0.2985 (2)	0.39298 (11)	0.0219 (3)
H5A	0.4999	0.185	0.4172	0.026*
H5B	0.6829	0.3811	0.4162	0.026*
O2	−0.0623 (2)	−0.34292 (17)	0.44188 (10)	0.0284 (3)
O3	0.2143 (2)	−0.06970 (17)	0.43144 (10)	0.0262 (3)
N2	0.3435 (2)	0.51522 (18)	0.27273 (10)	0.0158 (3)
H2	0.4806	0.6154	0.2854	0.019*
N4	0.0781 (3)	0.23345 (19)	0.27646 (10)	0.0167 (3)
H4	0.0176	0.1178	0.2937	0.02*
N1	−0.0104 (3)	−0.18948 (19)	0.39831 (10)	0.0171 (3)
C3	0.3308 (3)	0.3458 (2)	0.32034 (12)	0.0155 (3)
C2	0.0952 (3)	0.4958 (2)	0.20038 (12)	0.0165 (3)
C1	0.0296 (3)	0.6523 (2)	0.12995 (13)	0.0175 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0199 (5)	0.0212 (6)	0.0216 (6)	0.0009 (4)	−0.0034 (4)	0.0088 (5)
N3	0.0166 (6)	0.0160 (6)	0.0191 (7)	0.0023 (5)	−0.0004 (5)	0.0077 (5)
O4	0.0237 (6)	0.0185 (6)	0.0289 (6)	−0.0007 (5)	0.0009 (5)	0.0109 (5)
O5	0.0219 (6)	0.0198 (6)	0.0261 (6)	0.0013 (5)	−0.0043 (5)	0.0114 (5)
O1W	0.0219 (6)	0.0221 (6)	0.0343 (7)	−0.0020 (5)	−0.0057 (5)	0.0159 (5)
N5	0.0150 (6)	0.0186 (7)	0.0293 (8)	−0.0034 (5)	−0.0034 (5)	0.0123 (6)
O2	0.0274 (6)	0.0189 (6)	0.0339 (7)	−0.0075 (5)	−0.0047 (5)	0.0156 (5)
O3	0.0183 (6)	0.0212 (6)	0.0334 (7)	−0.0073 (5)	−0.0039 (5)	0.0105 (5)
N2	0.0135 (6)	0.0134 (6)	0.0190 (6)	−0.0007 (5)	0.0002 (5)	0.0060 (5)
N4	0.0149 (6)	0.0150 (6)	0.0195 (6)	0.0004 (5)	−0.0011 (5)	0.0095 (5)
N1	0.0166 (6)	0.0139 (6)	0.0195 (7)	−0.0002 (5)	0.0015 (5)	0.0047 (5)
C3	0.0153 (7)	0.0134 (7)	0.0177 (7)	0.0016 (5)	0.0023 (6)	0.0045 (6)
C2	0.0151 (7)	0.0153 (7)	0.0182 (7)	0.0021 (5)	0.0008 (6)	0.0042 (6)
C1	0.0201 (7)	0.0136 (7)	0.0187 (7)	0.0022 (6)	0.0031 (6)	0.0053 (6)

O1—N1	1.2720 (16)	N5—H5B	0.86
N3—C2	1.3023 (19)	O2—N1	1.2443 (16)
N3—N4	1.3779 (18)	O3—N1	1.2426 (16)
O4—C1	1.2139 (18)	N2—C3	1.3529 (19)
O5—C1	1.3051 (19)	N2—C2	1.3698 (19)
O5—H5	0.82	N2—H2	0.86
O1W—H2W	0.84 (3)	N4—C3	1.3443 (18)
O1W—H1W	0.86 (2)	N4—H4	0.86
N5—C3	1.3155 (19)	C2—C1	1.495 (2)
N5—H5A	0.86
C2—N3—N4	103.98 (12)	O3—N1—O2	120.44 (13)
C1—O5—H5	109.5	O3—N1—O1	119.79 (12)
H2W—O1W—H1W	107 (2)	O2—N1—O1	119.77 (12)
C3—N5—H5A	120	N5—C3—N4	126.95 (13)
C3—N5—H5B	120	N5—C3—N2	127.13 (13)
H5A—N5—H5B	120	N4—C3—N2	105.91 (12)
C3—N2—C2	106.57 (12)	N3—C2—N2	112.16 (13)
C3—N2—H2	126.7	N3—C2—C1	124.96 (14)
C2—N2—H2	126.7	N2—C2—C1	122.89 (13)
C3—N4—N3	111.38 (12)	O4—C1—O5	128.33 (15)
C3—N4—H4	124.3	O4—C1—C2	120.16 (14)
N3—N4—H4	124.3	O5—C1—C2	111.50 (13)
C2—N3—N4—C3	−0.23 (16)	C3—N2—C2—N3	0.52 (17)
N3—N4—C3—N5	−178.18 (15)	C3—N2—C2—C1	−179.10 (13)
N3—N4—C3—N2	0.55 (16)	N3—C2—C1—O4	−179.23 (15)
C2—N2—C3—N5	178.10 (15)	N2—C2—C1—O4	0.3 (2)
C2—N2—C3—N4	−0.62 (15)	N3—C2—C1—O5	0.5 (2)
N4—N3—C2—N2	−0.18 (16)	N2—C2—C1—O5	−179.93 (13)
N4—N3—C2—C1	179.43 (14)

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—H5A···O3	0.86	2.1	2.8672 (18)	148
N5—H5A···O3iii	0.86	2.44	3.0498 (19)	129
N5—H5B···O2iv	0.86	2.04	2.8352 (18)	154
N5—H5B···O2iii	0.86	2.41	3.0060 (18)	127
N2—H2···O1iv	0.86	2.02	2.8790 (17)	178
N4—H4···O1	0.86	2.06	2.9112 (18)	171
N4—H4···O3	0.86	2.42	3.0590 (18)	132
N4—H4···N1	0.86	2.59	3.4099 (19)	160

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

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