4-Nitro-N-(4-pyridinio)benzene­sulfonamidate monohydrate

Yu-Zhen Chen; Han Gao; Gang Li; Xiao-Jing Chen; Sheng-Yang Niu

doi:10.1107/S1600536808032273

. 2008 Oct 11;64(Pt 11):o2109. doi: 10.1107/S1600536808032273

4-Nitro-N-(4-pyridinio)benzenesulfonamidate monohydrate

Yu-Zhen Chen ^a,^*, Han Gao ^b, Gang Li ^b, Xiao-Jing Chen ^c, Sheng-Yang Niu ^b

PMCID: PMC2959784 PMID: 21580973

Abstract

The title compound, C₁₁H₉N₃O₄S·H₂O, contains both an acid and a base centre, and displays a zwitterionic structure in the solid state. The benzene ring makes an angle of 109.1 (2)° with the pyridinium ring. The crystal structure is stabilized by O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Allen et al. (1987 ▶); Li et al. (2007 ▶); Damiano et al. (2007 ▶); Yu & Li (2007 ▶).

Experimental

Crystal data

C₁₁H₉N₃O₄S·H₂O
M _r = 297.29
Monoclinic,
a = 6.7766 (14) Å
b = 8.3932 (17) Å
c = 21.717 (4) Å
β = 92.35 (3)°
V = 1234.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 113 (2) K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.932, T _max = 0.963
9708 measured reflections
2908 independent reflections
2022 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.136
S = 1.17
2908 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032273/at2641sup1.cif

e-64-o2109-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032273/at2641Isup2.hkl

e-64-o2109-Isup2.hkl^{(142.8KB, hkl)}

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—H5A⋯N2	0.85 (4)	1.97 (4)	2.813 (3)	167 (4)
O5—H5B⋯O2ⁱ	0.85 (5)	2.07 (5)	2.895 (3)	164 (4)
N1—H1A⋯O5ⁱⁱ	0.92 (4)	1.82 (4)	2.728 (3)	170 (4)

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

supplementary crystallographic information

Comment

Organic pyridinium salts have been widely used in the construction of supramolecular architectures (Teresa et al., 2007). As part of our ongoing studies of supramolecular chemistry involving the pyridinium rings (Li et al., 2007), the structure of the title compound (I) was determined by X-ray diffraction.

In the cations of (I) (Fig. 1), the short C—N distance [N2—C1 = 1.370 (3) Å] has a value between those of a typical C═N double and C—N single bond [1.47–1.50 Å and 1.34–1.38 Å, respectively; Allen et al., 1987]. This might be indicative of a slight π electron conjugation of the sulphonamide N with the pyridinium ring. The benzene ring exhibits an angle of 109.1 (2) ° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 2.2 (1) °.

The crystal structure is stabilized by O—H···N, O—H···O and N—H···O hydrogen bonds (Table 1).

Experimental

A solution of 4-nitrobenzenesulfonyl chloride (2.2 g, 10 mmol) in CH₂Cl₂ (10 ml) was added dropwise to a suspension of 4-aminopyridine (0.9 g, 10 mmol) in CH₂Cl₂ (10 ml) at room temperature with stirring. The reaction mixture was stirred overnight. The yellow solid obtained was washed with warm water to obtain the title compound in a yield of 55.3%. A colourless single-crystal suitable for X-ray analysis was obtained by slow evaporation of an acetic acid solution at room temperature over a period of a week.