4-(4-Nitro­benzene­sulfonamido)pyridinium bromide

Liang Zhao; Qi-Fei Yu; Qiong Wu

doi:10.1107/S1600536808035265

. 2008 Nov 13;64(Pt 12):o2308. doi: 10.1107/S1600536808035265

4-(4-Nitrobenzenesulfonamido)pyridinium bromide

Liang Zhao ^a,^*, Qi-Fei Yu ^b, Qiong Wu ^c

PMCID: PMC2960076 PMID: 21581285

Abstract

In the title compound, C₁₁H₁₀N₃O₄S⁺·Br⁻, the benzene ring makes an angle of 88.4 (2)° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 16.5 (2)°. The ions in the crystal structure are linked by a combination of intermolecular N—H⋯Br and non-conventional C—H⋯Br and C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For zwitterionic forms of N-arylbenzenesulfonamides, see: Li et al. (2007 ▶); Yu & Li (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For non-conventional hydrogen bonds, see: Desiraju & Steiner (2001 ▶). For the use of pyridinium derivatives in the construction of supramolecular architectures, see: Damiano et al. (2007 ▶).

Experimental

Crystal data

C₁₁H₁₀N₃O₄S⁺·Br⁻
M _r = 360.19
Monoclinic,
a = 38.242 (8) Å
b = 5.2852 (11) Å
c = 13.941 (3) Å
β = 108.18 (3)°
V = 2677.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 3.24 mm⁻¹
T = 113 (2) K
0.10 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.710, T _max = 0.938
10460 measured reflections
3174 independent reflections
2635 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.076
S = 1.05
3174 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.47 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/S1600536808035265/si2122sup1.cif

e-64-o2308-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035265/si2122Isup2.hkl

e-64-o2308-Isup2.hkl^{(155.8KB, 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
N1—H1A⋯Br1ⁱ	0.89 (3)	2.30 (3)	3.195 (2)	173 (3)
N2—H2A⋯Br1	0.84 (3)	2.38 (3)	3.225 (3)	174 (2)
C10—H10⋯O3ⁱⁱ	0.95	2.44	3.301 (3)	151
C5—H5⋯Br1ⁱⁱⁱ	0.95	2.75	3.676 (3)	165

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

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), an X-ray structure analysis of the title compound has been performed. In the cations of the title compound the short C—N distance [N2—C3 = 1.387 (3) Å] has a value between those of a typical C=N double and C—N single bond (1.34–1.38 Å and 1.47–1.50 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 makes an angle of 88.4 (2) ° with the pyridinium ring. The dihedral angle between the nitro group and the benzene ring is 163.5 (2) °. The S atom has a tetrahedral geometry and the Br anion link the cationic molecule into chains along the c axis. The ions in the crystal structure are linked by a combination of intermolecular N—H···Br and non-conventional C—H···Br and C—H···O hydrogen bonds (Table 1) to form a three-dimensional network (Desiraju & Steiner, 2001).

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 60.6%. A colorless single-crystal suitable for X-ray analysis was obtained by slow evaporation of an hydrobromic acid (5%) solution at room temperature over a period of a week. Analysis calculated for C₁₁H₁₀N₃O₄SBr: C 36.68, H 2.80, N 11.67%; found: C 36.70, H 2.52, N 11.98%.