1H-1,2,4-Triazol-4-ium 4-nitro­benzene­sulfonate monohydrate

Madhukar Hemamalini; Ibrahim Abdul Razak; Hoong-Kun Fun

doi:10.1107/S1600536811036774

. 2011 Sep 17;67(Pt 10):o2655. doi: 10.1107/S1600536811036774

1H-1,2,4-Triazol-4-ium 4-nitrobenzenesulfonate monohydrate

Madhukar Hemamalini ^a, Ibrahim Abdul Razak ^a,^‡, Hoong-Kun Fun ^a,^*,^§

PMCID: PMC3201373 PMID: 22065809

Abstract

In the 4-nitrobenzene sulfonate anion of the title compound, C₂H₄N₃ ⁺·C₆H₄NO₅S⁻·H₂O, 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 intermolecular 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 _r = 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
Δρ_max = 0.27 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-67-o2655-sup1.cif^{(16.7KB, cif)}

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

e-67-o2655-Isup2.hkl^{(129.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036774/is2774Isup3.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
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⋯O4^iv	0.93	2.36	3.063 (3)	132
C8—H8A⋯O1	0.93	2.54	3.186 (4)	126

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

Acknowledgments

MH, HKF and IAR thank the Ministry of Higher Education, Malaysia and Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/6711171. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

In recent years, there has been of great interest in the design and utilization of 1,2,4-triazole and its derivatives in coordination and biological chemistry for they represent the simple small molecular ligands. Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989) and in many other fields (Spungin et al., 1992; Jiang et al., 1990; Narayanan & Krakow, 1983). An X-ray study of the title compound was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure of the title compound (I).

The asymmetric unit of the title compound, (Fig. 1), contains a protonated 1,2,4-triazolinium cation, a 4-nitrobenzenesulfonate anion and a water molecule. In the 4-nitrobenzenesulfonate anion, the nitro and sulfonate groups are twisted slightly from the ring to which they are attached with the dihedral angles between the O1/O2/N1 and C1–C6 planes, and the S1/O3/O5 and C1–C6 planes being 2.8 (3) and 88.85 (13)°, respectively.

In the crystal structure, (Fig. 2), the ion pairs and water molecules are linked via intermolecular N—H···O, O—H···N, O—H···O and C—H···O hydrogen bonds (Table 1), forming two-dimensional networks parallel to (100). A short O···N contact of 2.87 Å is also observed.

Experimental

A methanol solution (20 ml) of 1-(p-Nitrobenzenesulfonayl)-1H-1,2,4-triazole (63.55 mg, Aldrich) was warmed over a heating magnetic stirrer for 15 minutes. The resulting solution was allowed to cool slowly at room temperature. Crystals of the title compound appeared from the mother liquor after a few days.