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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2429
doi:10.1107/S160053680803883X

4-(4-Nitro­benzene­sulfonamido)pyridinium nitrate

Liang-Bin Hu,a Yu-Xiang Ma,b Chang-Zhong Liuc and Ji-Guo Yangd*

aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, bCollege of Grain and Food, Henan University of Technology, Zhengzhou 450052, People's Republic of China, cSchool of Animal Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, and dCollege of Light Industry and Food Science, South China University of Technology, Guangzhou 510640, People's Republic of China
*Correspondence e-mail: jiguo_yang@yahoo.cn

(Received 11 November 2008; accepted 19 November 2008; online 22 November 2008)

A short C—N distance [1.394 (2) Å] in the title compound, C11H10N3O4S+·NO3−, is indicative of some conjugation of the sulfonamide π electrons with those of the pyridinium ring. The crystal structure is stabilized by N—H⋯O hydrogen bonds.

Related literature

For zwitterionic forms of N-aryl­benzene­sulfonamides, see: Li et al. (2007[Li, J. S., Chen, L. G., Zhang, Y. Y., Xu, Y. J., Deng, Y. & Huang, P. M. (2007). J. Chem. Res. 6, 350-352.]); Yu & Li (2007[Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.]). For reference geometrical data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). Damiano et al. (2007[Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735—2752.]) describe the use of pyridinium derivatives for the construction of supra­molecular architectures.

[Scheme 1]

Experimental

Crystal data

  • C11H10N3O4S+·NO3−

  • Mr = 342.29

  • Monoclinic, C 2/c

  • a = 36.516 (7) Å

  • b = 5.3742 (11) Å

  • c = 13.964 (3) Å

  • β = 99.54 (3)°

  • V = 2702.5 (10) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 113 (2) K

  • 0.20 × 0.12 × 0.04 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.94, Tmax = 0.99

  • 11804 measured reflections

  • 3203 independent reflections

  • 2648 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.09

  • 3203 reflections

  • 216 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O5 0.79 (2) 1.92 (2) 2.7020 (19) 171 (2)
N1—H1⋯O5i 0.92 (2) 1.93 (2) 2.7764 (19) 151 (2)
N1—H1⋯O6i 0.92 (2) 2.18 (3) 2.979 (2) 144.6 (19)
Symmetry code: (i) [x, -y, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803883X/bg2225sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803883X/bg2225Isup2.hkl

checkCIF report


Comment top

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 (2) 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 sulfonamide π electrons with those of the pyridinium ring. The dihedral angle between the benzene and the pyridinium rings is 81.3 (1) °, while the the one between the nitro group and the benzene ring is 16.1 (1) °.

Related literature top

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

Experimental top

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 60.5%. A colorless single-crystal suitable for X-ray analysis was obtained by slow evaporation of an nitric acid (10%) solution at room temperature over a period of a week.

Refinement top

The N-bound H atoms were located in a difference map and their coordinates were refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H =0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of one molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level (arbitrary spheres for the H atoms).
4-(4-Nitrobenzenesulfonamido)pyridinium nitrate top
Crystal data top
C11H10N3O4S+·NO3−F(000) = 1408
Mr = 342.29Dx = 1.683 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4207 reflections
a = 36.516 (7) Åθ = 2.3–27.9°
b = 5.3742 (11) ŵ = 0.29 mm−1
c = 13.964 (3) ÅT = 113 K
β = 99.54 (3)°Block, colorless
V = 2702.5 (10) Å30.20 × 0.12 × 0.04 mm
Z = 8
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3203 independent reflections
Radiation source: Rotating anode2648 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.037
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.3°
ω and ϕ scansh = −47→46
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −7→7
Tmin = 0.94, Tmax = 0.99l = −14→18
11804 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0612P)2 + 0.5371P]
where P = (Fo2 + 2Fc2)/3
3203 reflections(Δ/σ)max = 0.001
216 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.41 e Å−3
Crystal data top
C11H10N3O4S+·NO3−V = 2702.5 (10) Å3
Mr = 342.29Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.516 (7) ŵ = 0.29 mm−1
b = 5.3742 (11) ÅT = 113 K
c = 13.964 (3) Å0.20 × 0.12 × 0.04 mm
β = 99.54 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		3203 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2648 reflections with I > 2σ(I)
Tmin = 0.94, Tmax = 0.99Rint = 0.037
11804 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.30 e Å−3
3203 reflectionsΔρmin = −0.41 e Å−3
216 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.133115 (11)0.62515 (7)0.45086 (3)0.01800 (13)
O10.12702 (3)0.8195 (2)0.51613 (8)0.0246 (3)
O20.14580 (3)0.6801 (2)0.36175 (8)0.0256 (3)
O30.25592 (4)−0.2298 (3)0.63494 (9)0.0323 (3)
O40.22026 (4)−0.2269 (2)0.74432 (8)0.0285 (3)
N10.06215 (5)−0.1019 (3)0.23971 (11)0.0287 (4)
N20.09333 (4)0.4790 (2)0.42774 (10)0.0167 (3)
N30.22946 (4)−0.1490 (3)0.66941 (10)0.0211 (3)
C10.08430 (4)0.2815 (3)0.36372 (10)0.0158 (3)
C20.05600 (4)0.1211 (3)0.38117 (11)0.0186 (3)
H2A0.04410.14530.43610.022*
C30.04565 (5)−0.0704 (3)0.31855 (12)0.0259 (4)
H30.0268−0.18220.33040.031*
C40.08911 (5)0.0488 (3)0.22111 (12)0.0280 (4)
H40.10000.02220.16480.034*
C50.10119 (5)0.2409 (3)0.28211 (11)0.0223 (4)
H50.12080.34560.26940.027*
C60.16389 (4)0.4066 (3)0.51584 (11)0.0170 (3)
C70.18870 (5)0.2755 (3)0.46944 (11)0.0199 (3)
H70.19050.30980.40370.024*
C80.21072 (5)0.0943 (3)0.52069 (11)0.0203 (3)
H80.22790.00170.49090.024*
C90.20707 (4)0.0509 (3)0.61656 (11)0.0178 (3)
C100.18289 (5)0.1823 (3)0.66407 (11)0.0196 (3)
H100.18130.14920.73010.023*
C110.16114 (5)0.3626 (3)0.61267 (11)0.0195 (3)
H110.14430.45680.64320.023*
O50.06125 (3)0.4370 (2)0.58801 (8)0.0229 (3)
O60.01603 (3)0.5377 (2)0.66295 (8)0.0261 (3)
O70.02485 (4)0.7446 (2)0.53506 (8)0.0284 (3)
N40.03315 (4)0.5777 (2)0.59463 (9)0.0187 (3)
H10.0541 (7)−0.225 (5)0.1953 (16)0.050 (7)*
H20.0832 (6)0.483 (4)0.4735 (16)0.035 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0163 (2)0.0161 (2)0.0213 (2)−0.00180 (15)0.00217 (14)0.00219 (14)
O10.0227 (6)0.0169 (6)0.0324 (6)−0.0003 (5)−0.0007 (5)−0.0045 (5)
O20.0219 (6)0.0286 (7)0.0270 (6)−0.0035 (5)0.0062 (5)0.0110 (5)
O30.0306 (7)0.0354 (7)0.0299 (7)0.0162 (6)0.0023 (5)−0.0040 (6)
O40.0333 (7)0.0257 (7)0.0257 (6)0.0001 (6)0.0029 (5)0.0056 (5)
N10.0367 (10)0.0211 (8)0.0229 (7)0.0070 (7)−0.0106 (6)−0.0066 (6)
N20.0157 (7)0.0185 (7)0.0168 (6)−0.0016 (5)0.0049 (5)−0.0014 (5)
N30.0216 (8)0.0185 (7)0.0216 (7)0.0016 (6)−0.0012 (5)−0.0035 (5)
C10.0171 (7)0.0150 (7)0.0142 (7)0.0036 (6)−0.0009 (5)0.0020 (6)
C20.0167 (8)0.0189 (8)0.0192 (7)−0.0012 (6)0.0000 (6)0.0033 (6)
C30.0232 (9)0.0214 (9)0.0296 (9)−0.0017 (7)−0.0062 (7)0.0016 (7)
C40.0365 (11)0.0289 (9)0.0174 (8)0.0103 (8)0.0013 (7)−0.0014 (7)
C50.0253 (9)0.0247 (9)0.0174 (7)0.0052 (7)0.0052 (6)0.0030 (6)
C60.0149 (8)0.0173 (8)0.0185 (7)−0.0030 (6)0.0015 (5)−0.0006 (6)
C70.0179 (8)0.0243 (9)0.0183 (7)−0.0018 (7)0.0055 (6)0.0005 (6)
C80.0169 (8)0.0237 (9)0.0212 (8)0.0016 (7)0.0058 (6)−0.0039 (6)
C90.0155 (8)0.0177 (8)0.0193 (7)−0.0017 (6)0.0004 (6)−0.0023 (6)
C100.0210 (8)0.0220 (8)0.0158 (7)−0.0015 (7)0.0032 (6)−0.0023 (6)
C110.0192 (8)0.0212 (9)0.0185 (7)0.0004 (6)0.0048 (6)−0.0046 (6)
O50.0238 (6)0.0257 (6)0.0203 (6)0.0055 (5)0.0068 (4)0.0010 (5)
O60.0281 (7)0.0321 (7)0.0211 (6)0.0029 (5)0.0125 (5)0.0057 (5)
O70.0311 (7)0.0268 (7)0.0281 (6)0.0048 (6)0.0070 (5)0.0132 (5)
N40.0208 (7)0.0192 (7)0.0165 (6)−0.0017 (6)0.0040 (5)0.0008 (5)
Geometric parameters (Å, º) top
S1—O11.4277 (12)C4—C51.364 (2)
S1—O21.4286 (12)C4—H40.9500
S1—N21.6358 (14)C5—H50.9500
S1—C61.7687 (17)C6—C71.389 (2)
O3—N31.2281 (18)C6—C111.393 (2)
O4—N31.2243 (17)C7—C81.385 (2)
N1—C41.333 (3)C7—H70.9500
N1—C31.350 (2)C8—C91.387 (2)
N1—H10.92 (2)C8—H80.9500
N2—C11.392 (2)C9—C101.383 (2)
N2—H20.79 (2)C10—C111.377 (2)
N3—C91.472 (2)C10—H100.9500
C1—C21.398 (2)C11—H110.9500
C1—C51.400 (2)O5—N41.2902 (17)
C2—C31.363 (2)O6—N41.2427 (16)
C2—H2A0.9500O7—N41.2270 (17)
C3—H30.9500
O1—S1—O2120.81 (7)C5—C4—H4119.6
O1—S1—N2104.46 (7)C4—C5—C1119.05 (16)
O2—S1—N2109.44 (8)C4—C5—H5120.5
O1—S1—C6108.14 (7)C1—C5—H5120.5
O2—S1—C6108.30 (8)C7—C6—C11121.62 (15)
N2—S1—C6104.51 (7)C7—C6—S1120.35 (12)
C4—N1—C3121.75 (15)C11—C6—S1117.96 (12)
C4—N1—H1118.0 (14)C8—C7—C6118.90 (14)
C3—N1—H1120.2 (14)C8—C7—H7120.5
C1—N2—S1126.95 (11)C6—C7—H7120.5
C1—N2—H2116.5 (16)C7—C8—C9118.47 (15)
S1—N2—H2110.4 (16)C7—C8—H8120.8
O4—N3—O3123.99 (14)C9—C8—H8120.8
O4—N3—C9118.02 (14)C10—C9—C8123.25 (15)
O3—N3—C9117.99 (13)C10—C9—N3118.54 (14)
N2—C1—C2117.50 (13)C8—C9—N3118.19 (14)
N2—C1—C5123.52 (15)C11—C10—C9117.92 (14)
C2—C1—C5118.95 (14)C11—C10—H10121.0
C3—C2—C1119.22 (15)C9—C10—H10121.0
C3—C2—H2A120.4C10—C11—C6119.82 (15)
C1—C2—H2A120.4C10—C11—H11120.1
N1—C3—C2120.27 (17)C6—C11—H11120.1
N1—C3—H3119.9O7—N4—O6123.22 (14)
C2—C3—H3119.9O7—N4—O5119.33 (13)
N1—C4—C5120.74 (16)O6—N4—O5117.45 (13)
N1—C4—H4119.6
O1—S1—N2—C1176.50 (13)O2—S1—C6—C11167.74 (12)
O2—S1—N2—C145.81 (15)N2—S1—C6—C11−75.67 (14)
C6—S1—N2—C1−69.99 (14)C11—C6—C7—C81.1 (2)
S1—N2—C1—C2154.93 (12)S1—C6—C7—C8−175.84 (12)
S1—N2—C1—C5−27.1 (2)C6—C7—C8—C90.0 (2)
N2—C1—C2—C3178.18 (14)C7—C8—C9—C10−1.0 (2)
C5—C1—C2—C30.1 (2)C7—C8—C9—N3177.55 (15)
C4—N1—C3—C20.9 (3)O4—N3—C9—C1015.6 (2)
C1—C2—C3—N1−1.1 (2)O3—N3—C9—C10−165.41 (15)
C3—N1—C4—C50.4 (3)O4—N3—C9—C8−163.03 (15)
N1—C4—C5—C1−1.4 (3)O3—N3—C9—C816.0 (2)
N2—C1—C5—C4−176.80 (15)C8—C9—C10—C110.8 (2)
C2—C1—C5—C41.2 (2)N3—C9—C10—C11−177.68 (14)
O1—S1—C6—C7−147.78 (13)C9—C10—C11—C60.3 (2)
O2—S1—C6—C7−15.24 (16)C7—C6—C11—C10−1.2 (2)
N2—S1—C6—C7101.35 (14)S1—C6—C11—C10175.76 (13)
O1—S1—C6—C1135.21 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O50.79 (2)1.92 (2)2.7020 (19)171 (2)
N1—H1···O5i0.92 (2)1.93 (2)2.7764 (19)151 (2)
N1—H1···O6i0.92 (2)2.18 (3)2.979 (2)144.6 (19)
Symmetry code: (i) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formulaC11H10N3O4S+·NO3−
Mr342.29
Crystal system, space groupMonoclinic, C2/c
Temperature (K)113
a, b, c (Å)36.516 (7), 5.3742 (11), 13.964 (3)
β (°) 99.54 (3)
V (Å3)2702.5 (10)
Z8
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.20 × 0.12 × 0.04
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.94, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections		11804, 3203, 2648
Rint0.037
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.107, 1.10
No. of reflections3203
No. of parameters216
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.30, −0.41

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O50.79 (2)1.92 (2)2.7020 (19)171 (2)
N1—H1···O5i0.92 (2)1.93 (2)2.7764 (19)151 (2)
N1—H1···O6i0.92 (2)2.18 (3)2.979 (2)144.6 (19)
Symmetry code: (i) x, −y, z−1/2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
 First citationDamiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735—2752.  Web of Science CrossRef Google Scholar
 First citationLi, J. S., Chen, L. G., Zhang, Y. Y., Xu, Y. J., Deng, Y. & Huang, P. M. (2007). J. Chem. Res. 6, 350–352.  CrossRef Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.  CSD CrossRef IUCr Journals Google Scholar

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COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2429
doi:10.1107/S160053680803883X
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