Bis(5-amino-3-carb-oxy-1H-1,2,4-triazol-4-ium) sulfate dihydrate.

The crystal structure of the title compound, 2C(3)H(5)N(4)O(2) (+)·SO(4) (2-)·2H(2)O, displays a three-dimensional framework in which mixed infinite chains [oriented parallel to (510) and ([Formula: see text]10)] inter-fere, forming tunnels extending parallel to the c axis. Inter-molecular O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds ensure the unity of the structure and generate centrosymmetric R(4) (4)(14) and R(4) (2)(8) rings. The S atom lies on a twofold axis.

Related literature

For uses of 1,2,4 triazole derivatives, see: Beckmann & Brooker, (2003 ▶); Bhargava et al. (1981 ▶); Fujigaya et al. (2003 ▶); Hirota et al. (1991 ▶); Li et al. (2004 ▶); Matulková et al. (2008 ▶). For related hybrid compounds, see: Berrah et al. (2011a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

2C3H5N4O2 +·SO4 2−·2H2O

M = 390.31

Monoclinic,

a = 19.4350 (9) Å

b = 5.8467 (2) Å

c = 13.3343 (6) Å

β = 109.981 (2)°

V = 1423.98 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 150 K

0.48 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer

11018 measured reflections

1620 independent reflections

1470 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.08

1620 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811013882/bq2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013882/bq2295Isup2.hkl

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

2C3H5N4O2+·SO42−·2H2O	F(000) = 808
Mr = 390.31	Dx = 1.821 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.4350 (9) Å	Cell parameters from 1620 reflections
b = 5.8467 (2) Å	θ = 3.3–27.4°
c = 13.3343 (6) Å	µ = 0.31 mm−1
β = 109.981 (2)°	T = 150 K
V = 1423.98 (10) Å3	Needle, colourless
Z = 4	0.48 × 0.08 × 0.06 mm

Bruker APEXII diffractometer	Rint = 0.032
graphite	θmax = 27.5°, θmin = 3.3°
CCD rotation images, thin slices scans	h = −24→25
11018 measured reflections	k = −7→7
1620 independent reflections	l = −17→15
1470 reflections with I > 2σ(I)

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0343P)2 + 1.9446P] where P = (Fo2 + 2Fc2)/3
1620 reflections	(Δ/σ)max = 0.009
121 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.41 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
C1	0.32927 (7)	0.3566 (2)	0.60560 (11)	0.0136 (3)
C2	0.35578 (7)	0.2304 (2)	0.52873 (11)	0.0123 (3)
C3	0.40656 (7)	−0.0381 (2)	0.46589 (11)	0.0129 (3)
N1	0.38002 (6)	0.1265 (2)	0.39270 (9)	0.0138 (3)
H1	0.3827	0.125	0.3296	0.017*
N2	0.34797 (6)	0.2981 (2)	0.43222 (9)	0.0138 (3)
N3	0.39065 (6)	0.0245 (2)	0.55278 (9)	0.0123 (2)
H3	0.4005	−0.0502	0.6116	0.015*
N4	0.44239 (7)	−0.2252 (2)	0.45703 (10)	0.0169 (3)
H4A	0.451	−0.2519	0.399	0.02*
H4B	0.4571	−0.3201	0.5093	0.02*
O1	0.33947 (6)	0.28073 (19)	0.69430 (8)	0.0188 (2)
O2	0.29439 (6)	0.54386 (18)	0.56322 (8)	0.0186 (2)
H2	0.2817	0.612	0.6077	0.028*
O3	0.48758 (5)	0.50548 (17)	0.65377 (8)	0.0158 (2)
O4	0.56503 (6)	0.79464 (19)	0.76558 (8)	0.0190 (2)
S1	0.5	0.64445 (8)	0.75	0.01101 (13)
O1W	0.25419 (6)	0.69140 (19)	0.32536 (9)	0.0194 (2)
H1W	0.2751 (11)	0.724 (4)	0.2772 (17)	0.029*
H2W	0.2786 (11)	0.586 (4)	0.3624 (17)	0.029*

	U11	U22	U33	U12	U13	U23
C1	0.0118 (6)	0.0150 (7)	0.0148 (7)	−0.0021 (5)	0.0054 (5)	−0.0017 (5)
C2	0.0117 (6)	0.0128 (6)	0.0122 (7)	−0.0015 (5)	0.0037 (5)	−0.0008 (5)
C3	0.0119 (6)	0.0151 (7)	0.0117 (6)	−0.0026 (5)	0.0040 (5)	−0.0008 (5)
N1	0.0177 (6)	0.0155 (6)	0.0097 (6)	0.0011 (5)	0.0066 (5)	−0.0003 (4)
N2	0.0150 (6)	0.0143 (6)	0.0126 (6)	−0.0001 (4)	0.0053 (5)	−0.0008 (4)
N3	0.0145 (5)	0.0138 (6)	0.0093 (5)	0.0010 (4)	0.0052 (4)	0.0015 (4)
N4	0.0220 (6)	0.0162 (6)	0.0145 (6)	0.0034 (5)	0.0087 (5)	−0.0002 (5)
O1	0.0230 (5)	0.0213 (5)	0.0155 (5)	0.0024 (4)	0.0108 (4)	0.0015 (4)
O2	0.0227 (5)	0.0175 (5)	0.0170 (5)	0.0062 (4)	0.0086 (4)	−0.0006 (4)
O3	0.0182 (5)	0.0164 (5)	0.0125 (5)	−0.0004 (4)	0.0051 (4)	−0.0035 (4)
O4	0.0221 (5)	0.0243 (6)	0.0133 (5)	−0.0105 (4)	0.0094 (4)	−0.0049 (4)
S1	0.0129 (2)	0.0119 (2)	0.0090 (2)	0	0.00474 (17)	0
O1W	0.0228 (6)	0.0202 (5)	0.0187 (6)	0.0065 (4)	0.0117 (5)	0.0044 (4)

C1—O1	1.2144 (18)	N3—H3	0.86
C1—O2	1.3098 (17)	N4—H4A	0.86
C1—C2	1.4905 (19)	N4—H4B	0.86
C2—N2	1.3046 (18)	O2—H2	0.82
C2—N3	1.3648 (18)	O3—S1	1.4674 (10)
C3—N4	1.3236 (19)	O4—S1	1.4941 (10)
C3—N1	1.3420 (18)	S1—O3i	1.4674 (10)
C3—N3	1.3480 (18)	S1—O4i	1.4941 (10)
N1—N2	1.3774 (17)	O1W—H1W	0.89 (2)
N1—H1	0.86	O1W—H2W	0.83 (2)
O1—C1—O2	127.86 (13)	C3—N3—H3	126.9
O1—C1—C2	120.61 (13)	C2—N3—H3	126.9
O2—C1—C2	111.50 (12)	C3—N4—H4A	120
N2—C2—N3	112.37 (12)	C3—N4—H4B	120
N2—C2—C1	125.24 (13)	H4A—N4—H4B	120
N3—C2—C1	122.38 (12)	C1—O2—H2	109.5
N4—C3—N1	127.67 (13)	O3—S1—O3i	112.76 (9)
N4—C3—N3	125.69 (13)	O3—S1—O4	109.00 (6)
N1—C3—N3	106.63 (12)	O3i—S1—O4	108.98 (6)
C3—N1—N2	110.85 (11)	O3—S1—O4i	108.98 (6)
C3—N1—H1	124.6	O3i—S1—O4i	109.00 (6)
N2—N1—H1	124.6	O4—S1—O4i	108.01 (9)
C2—N2—N1	103.94 (11)	H1W—O1W—H2W	106.3 (19)
C3—N3—C2	106.20 (11)
O1—C1—C2—N2	−179.54 (13)	C1—C2—N2—N1	−179.34 (12)
O2—C1—C2—N2	2.06 (19)	C3—N1—N2—C2	−0.42 (14)
O1—C1—C2—N3	1.6 (2)	N4—C3—N3—C2	177.99 (13)
O2—C1—C2—N3	−176.82 (12)	N1—C3—N3—C2	−1.19 (14)
N4—C3—N1—N2	−178.13 (13)	N2—C2—N3—C3	1.00 (16)
N3—C3—N1—N2	1.03 (15)	C1—C2—N3—C3	−179.99 (12)
N3—C2—N2—N1	−0.37 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···N2	0.83 (2)	2.16 (2)	2.9774 (16)	169 (2)
O1W—H1W···O1ii	0.89 (2)	1.93 (2)	2.7941 (17)	163 (2)
O2—H2···O1Wiii	0.82	1.74	2.5403 (16)	165
N1—H1···O4iv	0.86	1.94	2.7107 (16)	149
N3—H3···O4v	0.86	1.79	2.6436 (15)	171
N4—H4A···O3vi	0.86	2.17	2.8452 (17)	136
N4—H4B···O3vii	0.86	2.08	2.9255 (16)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯N2	0.83 (2)	2.16 (2)	2.9774 (16)	169 (2)
O1W—H1W⋯O1i	0.89 (2)	1.93 (2)	2.7941 (17)	163 (2)
O2—H2⋯O1Wii	0.82	1.74	2.5403 (16)	165
N1—H1⋯O4iii	0.86	1.94	2.7107 (16)	149
N3—H3⋯O4iv	0.86	1.79	2.6436 (15)	171
N4—H4A⋯O3v	0.86	2.17	2.8452 (17)	136
N4—H4B⋯O3vi	0.86	2.08	2.9255 (16)	168

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