4-(4-Nitro­benzene­sulfonamido)pyri­dinium chloride

Hao Zhang; Yu-Xiang Ma; Lin Zhou; Hai-Zhen Mo

doi:10.1107/S1600536808032054

. 2008 Oct 9;64(Pt 11):o2091. doi: 10.1107/S1600536808032054

4-(4-Nitrobenzenesulfonamido)pyridinium chloride

Hao Zhang ^a, Yu-Xiang Ma ^b, Lin Zhou ^c, Hai-Zhen Mo ^a,^*

PMCID: PMC2959751 PMID: 21580955

Abstract

In the title compound, C₁₁H₁₀N₃O₄S⁺·Cl⁻, the benzene ring makes an angle of 89.2 (1)° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 15.7 (1)°. The crystal structure is stabilized by N—H⋯Cl hydrogen bonds.

Related literature

For zwitterionic forms of N-arylbenzenesulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For reference geometric data, see: Allen et al. (1987 ▶). Damiano et al. (2007 ▶) describe the use of pyridinium derivatives for the construction of supramolecular architectures.

Experimental

Crystal data

C₁₁H₁₀N₃O₄S⁺·Cl⁻
M _r = 315.73
Monoclinic,
a = 37.942 (8) Å
b = 5.2446 (10) Å
c = 13.713 (3) Å
β = 107.77 (3)°
V = 2598.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 113 (2) K
0.12 × 0.10 × 0.08 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
9693 measured reflections
2865 independent reflections
2330 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.107
S = 1.06
2865 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.48 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/S1600536808032054/zl2146sup1.cif

e-64-o2091-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032054/zl2146Isup2.hkl

e-64-o2091-Isup2.hkl^{(140.7KB, 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
N1—H1⋯Cl1ⁱ	0.93 (3)	2.12 (3)	3.039 (2)	171 (3)
N2—H2A⋯Cl1ⁱⁱ	0.89 (3)	2.18 (3)	3.066 (2)	173 (3)

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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 (Damiano 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 was determined by X-ray diffraction. In the cations of the title compound the short C—N distance [N2—C1 = 1.394 (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 conjugation of the sulphonamide π electrons N with those of the pyridinium ring. The benzene ring exhibits an angle of 89.2 (1)° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 164.3 (1)°. The crystal packing is stabilized by N—H···Cl hydrogen bonds (Table 1). Fig. 2 showing supramolecular chains linked by N—H···Cl hydrogen bonds.

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 61.6%. A colorless single-crystal suitable for X-ray analysis was obtained by slow evaporation of an hydrochloric acid (10%) solution at room temperature over a period of a week. Analysis calculated for C₁₁H₁₀N₃O₄SCl: C 41.84, H 3.19, N 13.31%; found: C 41.95, H 3.52, N 13.69%.