1H-1,2,4-Triazol-4-ium 4-nitro-benzene-sulfonate monohydrate.

In the 4-nitro-benzene sulfonate anion of the title compound, C(2)H(4)N(3) (+)·C(6)H(4)NO(5)S(-)·H(2)O, the nitro group is slightly twisted from the plane of the benzene ring [dihedral angle = 2.8 (3)°]. In the crystal, the three components are linked via N-H⋯O, O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. A short inter-molecular O⋯N contact of 2.872 (3) Å is also observed between the nitro and sulfonate groups.

Related literature

For details and applications of aromatic sulfonates, see: Yachi et al. (1989 ▶); Spungin et al. (1992 ▶); Jiang et al. (1990 ▶); Narayanan & Krakow (1983 ▶).

Experimental

Crystal data

C2H4N3 +·C6H4NO5S−·H2O

M = 290.26

Monoclinic,

a = 14.0931 (13) Å

b = 6.4859 (6) Å

c = 14.5707 (14) Å

β = 117.182 (2)°

V = 1184.77 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.41 × 0.28 × 0.05 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.885, T max = 0.986

10925 measured reflections

2692 independent reflections

2136 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.144

S = 1.07

2692 reflections

188 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036774/is2774sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036774/is2774Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036774/is2774Isup3.cml

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

C2H4N3+·C6H4NO5S−·H2O	F(000) = 600
Mr = 290.26	Dx = 1.627 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3747 reflections
a = 14.0931 (13) Å	θ = 2.8–30.9°
b = 6.4859 (6) Å	µ = 0.31 mm−1
c = 14.5707 (14) Å	T = 296 K
β = 117.182 (2)°	Block, colourless
V = 1184.77 (19) Å3	0.41 × 0.28 × 0.05 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	2136 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→16
Tmin = 0.885, Tmax = 0.986	k = −8→8
10925 measured reflections	l = −18→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0862P)2 + 0.2559P] where P = (Fo2 + 2Fc2)/3
2692 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1W	0.09777 (16)	0.2748 (3)	0.10622 (14)	0.0521 (5)
H2W	0.165 (2)	0.336 (7)	0.125 (4)	0.126 (16)*
H1W	0.066 (3)	0.338 (7)	0.141 (3)	0.130 (18)*
O3	0.72455 (14)	−0.0217 (3)	0.38351 (14)	0.0535 (5)
O4	0.83055 (14)	0.2569 (3)	0.49177 (16)	0.0520 (5)
O5	0.75198 (13)	0.0065 (3)	0.55875 (13)	0.0441 (4)
N1	0.34545 (15)	0.6163 (3)	0.32475 (15)	0.0384 (5)
C1	0.62491 (17)	0.4703 (4)	0.39475 (18)	0.0357 (5)
H1A	0.6865	0.5296	0.3982	0.043*
C2	0.53180 (18)	0.5842 (3)	0.35933 (18)	0.0360 (5)
H2A	0.5293	0.7195	0.3373	0.043*
C3	0.44280 (16)	0.4921 (3)	0.35755 (16)	0.0313 (5)
C4	0.44120 (17)	0.2906 (4)	0.38632 (18)	0.0365 (5)
H4A	0.3795	0.2324	0.3832	0.044*
C5	0.53449 (17)	0.1771 (4)	0.42016 (18)	0.0355 (5)
H5A	0.5359	0.0402	0.4397	0.043*
C6	0.62590 (16)	0.2680 (3)	0.42492 (15)	0.0293 (4)
S1	0.74353 (4)	0.11570 (9)	0.46843 (4)	0.03281 (19)
O1	0.26690 (14)	0.5340 (3)	0.32361 (16)	0.0553 (5)
O2	0.34762 (14)	0.7968 (3)	0.30119 (15)	0.0513 (5)
C7	−0.08790 (19)	0.3289 (4)	0.33222 (18)	0.0377 (5)
H7A	−0.1481	0.3087	0.3418	0.045*
C8	0.07316 (18)	0.3574 (4)	0.35568 (19)	0.0386 (5)
H8A	0.1473	0.3593	0.3885	0.046*
N2	0.01283 (16)	0.3160 (3)	0.40391 (16)	0.0372 (4)
H1NA	−0.141 (3)	0.397 (4)	0.185 (3)	0.057 (9)*
N3	0.01514 (15)	0.3939 (3)	0.25866 (15)	0.0378 (5)
N4	−0.08644 (15)	0.3754 (3)	0.24581 (16)	0.0356 (4)
H1NB	0.033 (2)	0.284 (4)	0.467 (3)	0.056 (9)*

	U11	U22	U33	U12	U13	U23
O1W	0.0560 (12)	0.0645 (12)	0.0418 (10)	−0.0220 (9)	0.0277 (9)	−0.0133 (9)
O3	0.0481 (10)	0.0691 (12)	0.0361 (9)	0.0226 (9)	0.0128 (8)	−0.0110 (9)
O4	0.0309 (9)	0.0637 (12)	0.0627 (12)	−0.0006 (7)	0.0225 (8)	0.0041 (9)
O5	0.0381 (9)	0.0573 (10)	0.0332 (9)	0.0099 (7)	0.0131 (7)	0.0110 (8)
N1	0.0338 (10)	0.0511 (12)	0.0294 (10)	0.0095 (8)	0.0136 (8)	0.0016 (9)
C1	0.0303 (10)	0.0394 (11)	0.0397 (12)	−0.0027 (9)	0.0179 (9)	0.0001 (10)
C2	0.0378 (12)	0.0345 (11)	0.0376 (12)	0.0023 (9)	0.0188 (9)	0.0036 (9)
C3	0.0289 (10)	0.0382 (11)	0.0250 (10)	0.0054 (8)	0.0108 (8)	−0.0016 (9)
C4	0.0273 (10)	0.0432 (12)	0.0400 (13)	−0.0006 (9)	0.0163 (9)	0.0011 (10)
C5	0.0345 (11)	0.0352 (11)	0.0397 (12)	0.0022 (9)	0.0195 (10)	0.0049 (10)
C6	0.0284 (10)	0.0374 (11)	0.0229 (10)	0.0026 (8)	0.0126 (8)	−0.0001 (8)
S1	0.0276 (3)	0.0439 (3)	0.0256 (3)	0.0065 (2)	0.0110 (2)	0.0010 (2)
O1	0.0336 (9)	0.0730 (12)	0.0644 (13)	0.0111 (8)	0.0267 (8)	0.0157 (10)
O2	0.0509 (11)	0.0436 (10)	0.0545 (12)	0.0141 (8)	0.0199 (9)	0.0063 (9)
C7	0.0367 (12)	0.0416 (12)	0.0370 (12)	−0.0036 (10)	0.0188 (10)	−0.0047 (10)
C8	0.0335 (11)	0.0392 (12)	0.0407 (13)	−0.0020 (9)	0.0149 (10)	−0.0004 (10)
N2	0.0414 (11)	0.0373 (10)	0.0298 (11)	0.0010 (8)	0.0136 (8)	0.0021 (8)
N3	0.0375 (10)	0.0408 (10)	0.0369 (11)	−0.0075 (8)	0.0186 (8)	0.0011 (8)
N4	0.0312 (9)	0.0402 (10)	0.0309 (10)	−0.0045 (8)	0.0102 (8)	−0.0015 (8)

O1W—H2W	0.950 (18)	C4—C5	1.386 (3)
O1W—H1W	0.917 (18)	C4—H4A	0.9300
O3—S1	1.4472 (18)	C5—C6	1.389 (3)
O4—S1	1.4411 (18)	C5—H5A	0.9300
O5—S1	1.4508 (18)	C6—S1	1.779 (2)
N1—O1	1.222 (3)	C7—N4	1.304 (3)
N1—O2	1.224 (3)	C7—N2	1.326 (3)
N1—C3	1.470 (3)	C7—H7A	0.9300
C1—C6	1.382 (3)	C8—N3	1.291 (3)
C1—C2	1.384 (3)	C8—N2	1.355 (3)
C1—H1A	0.9300	C8—H8A	0.9300
C2—C3	1.379 (3)	N2—H1NB	0.86 (3)
C2—H2A	0.9300	N3—N4	1.362 (3)
C3—C4	1.376 (3)	N4—H1NA	0.87 (3)
H2W—O1W—H1W	110 (3)	C5—C6—S1	118.29 (16)
O1—N1—O2	123.5 (2)	O4—S1—O3	113.45 (12)
O1—N1—C3	118.0 (2)	O4—S1—O5	112.82 (11)
O2—N1—C3	118.42 (19)	O3—S1—O5	112.42 (12)
C6—C1—C2	119.7 (2)	O4—S1—C6	106.58 (10)
C6—C1—H1A	120.1	O3—S1—C6	105.01 (10)
C2—C1—H1A	120.1	O5—S1—C6	105.75 (10)
C3—C2—C1	118.4 (2)	N4—C7—N2	107.0 (2)
C3—C2—H2A	120.8	N4—C7—H7A	126.5
C1—C2—H2A	120.8	N2—C7—H7A	126.5
C4—C3—C2	123.16 (19)	N3—C8—N2	111.8 (2)
C4—C3—N1	118.48 (19)	N3—C8—H8A	124.1
C2—C3—N1	118.35 (19)	N2—C8—H8A	124.1
C3—C4—C5	117.9 (2)	C7—N2—C8	106.2 (2)
C3—C4—H4A	121.0	C7—N2—H1NB	125 (2)
C5—C4—H4A	121.0	C8—N2—H1NB	129 (2)
C4—C5—C6	120.0 (2)	C8—N3—N4	103.57 (19)
C4—C5—H5A	120.0	C7—N4—N3	111.5 (2)
C6—C5—H5A	120.0	C7—N4—H1NA	128 (2)
C1—C6—C5	120.84 (19)	N3—N4—H1NA	121 (2)
C1—C6—S1	120.85 (16)
C6—C1—C2—C3	1.4 (3)	C4—C5—C6—S1	−179.78 (17)
C1—C2—C3—C4	−2.0 (3)	C1—C6—S1—O4	16.1 (2)
C1—C2—C3—N1	177.05 (19)	C5—C6—S1—O4	−165.17 (17)
O1—N1—C3—C4	−0.7 (3)	C1—C6—S1—O3	−104.6 (2)
O2—N1—C3—C4	178.5 (2)	C5—C6—S1—O3	74.2 (2)
O1—N1—C3—C2	−179.8 (2)	C1—C6—S1—O5	136.35 (19)
O2—N1—C3—C2	−0.6 (3)	C5—C6—S1—O5	−44.87 (19)
C2—C3—C4—C5	1.1 (3)	N4—C7—N2—C8	0.1 (3)
N1—C3—C4—C5	−178.02 (19)	N3—C8—N2—C7	−0.3 (3)
C3—C4—C5—C6	0.5 (3)	N2—C8—N3—N4	0.3 (3)
C2—C1—C6—C5	0.0 (3)	N2—C7—N4—N3	0.0 (3)
C2—C1—C6—S1	178.76 (17)	C8—N3—N4—C7	−0.2 (2)
C4—C5—C6—C1	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1NA···O5i	0.88 (4)	1.88 (4)	2.744 (3)	169 (2)
O1W—H1W···N3	0.91 (4)	2.17 (4)	3.041 (3)	160 (4)
N2—H1NB···O1Wii	0.86 (4)	1.84 (4)	2.692 (3)	171 (3)
O1W—H2W···O3iii	0.95 (4)	1.86 (4)	2.774 (3)	161 (5)
C7—H7A···O4iv	0.93	2.36	3.063 (3)	132.
C8—H8A···O1	0.93	2.54	3.186 (4)	126.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1NA⋯O5i	0.88 (4)	1.88 (4)	2.744 (3)	169 (2)
O1W—H1W⋯N3	0.91 (4)	2.17 (4)	3.041 (3)	160 (4)
N2—H1NB⋯O1Wii	0.86 (4)	1.84 (4)	2.692 (3)	171 (3)
O1W—H2W⋯O3iii	0.95 (4)	1.86 (4)	2.774 (3)	161 (5)
C7—H7A⋯O4iv	0.93	2.36	3.063 (3)	132
C8—H8A⋯O1	0.93	2.54	3.186 (4)	126

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