Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2109
doi:10.1107/S1600536808032273

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

Yu-Zhen Chen,a* Han Gao,b Gang Li,b Xiao-Jing Chenc and Sheng-Yang Niub

aDepartment of Mathematics, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, bSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China, and cXinke College, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China
*Correspondence e-mail: chen_yuzhen@yahoo.cn

(Received 27 September 2008; accepted 7 October 2008; online 11 October 2008)

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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.]); 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.]); Damiano et al. (2007[Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735-2752.]); Yu & Li (2007[Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.]).

[Scheme 1]

Experimental

Crystal data

  • C11H9N3O4S·H2O

  • Mr = 297.29

  • Monoclinic, P 21 /n

  • 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.932, Tmax = 0.963

  • 9708 measured reflections

  • 2908 independent reflections

  • 2022 reflections with I > 2σ(I)

  • Rint = 0.061
Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.136

  • S = 1.17

  • 2908 reflections

  • 193 parameters

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

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.45 e Å−3

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)
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, 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/S1600536808032273/at2641sup1.cif

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

checkCIF report


Comment top

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).

Related literature top

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

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 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.

Refinement top

The H atoms of the water molecule were found on a difference Fourier map and refined freely. 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 = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 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. Molecular view of the title compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level (arbitrary spheres for the H atoms).
4-Nitro-N-(4-pyridinio)benzenesulfonamidate monohydrate top
Crystal data top
C11H9N3O4S·H2OF(000) = 616
Mr = 297.29Dx = 1.600 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3340 reflections
a = 6.7766 (14) Åθ = 1.9–27.9°
b = 8.3932 (17) ŵ = 0.29 mm−1
c = 21.717 (4) ÅT = 113 K
β = 92.35 (3)°Block, colourless
V = 1234.2 (4) Å30.20 × 0.18 × 0.12 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		2908 independent reflections
Radiation source: rotating anode2022 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.061
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω and ϕ scansh = −8→7
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		k = −11→10
Tmin = 0.932, Tmax = 0.963l = −19→28
9708 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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.031P)2 + 1.5168P]
where P = (Fo2 + 2Fc2)/3
2908 reflections(Δ/σ)max = 0.002
193 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
C11H9N3O4S·H2OV = 1234.2 (4) Å3
Mr = 297.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.7766 (14) ŵ = 0.29 mm−1
b = 8.3932 (17) ÅT = 113 K
c = 21.717 (4) Å0.20 × 0.18 × 0.12 mm
β = 92.35 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer		2908 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)		2022 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.963Rint = 0.061
9708 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.35 e Å−3
2908 reflectionsΔρmin = −0.45 e Å−3
193 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
S10.89206 (11)0.18818 (8)0.12547 (3)0.01574 (18)
N10.7145 (4)0.7176 (3)0.00969 (13)0.0228 (6)
H1A0.707 (6)0.823 (5)−0.0019 (19)0.048 (12)*
N20.8061 (4)0.2477 (3)0.06005 (11)0.0166 (5)
N30.2350 (4)0.1341 (3)0.29976 (12)0.0236 (6)
O11.0378 (3)0.2937 (2)0.15368 (9)0.0197 (5)
O20.9523 (3)0.0240 (2)0.11577 (10)0.0208 (5)
O30.2477 (4)0.2106 (3)0.34777 (10)0.0332 (6)
O40.0934 (4)0.0497 (3)0.28506 (13)0.0401 (7)
C10.7738 (4)0.4058 (3)0.04742 (13)0.0151 (6)
C20.7618 (5)0.5312 (3)0.09068 (14)0.0203 (6)
H20.77360.50990.13360.024*
C30.7329 (5)0.6835 (4)0.06978 (16)0.0259 (7)
H30.72570.76770.09890.031*
C40.7199 (5)0.6006 (4)−0.03300 (14)0.0204 (6)
H40.70530.6265−0.07550.024*
C50.7463 (4)0.4454 (3)−0.01543 (14)0.0176 (6)
H50.74620.3638−0.04580.021*
C60.6953 (4)0.1762 (3)0.17671 (13)0.0150 (6)
C70.5306 (5)0.0811 (3)0.16067 (13)0.0182 (6)
H70.52300.02750.12210.022*
C80.3798 (5)0.0659 (3)0.20114 (14)0.0180 (6)
H80.26780.00130.19120.022*
C90.3961 (4)0.1475 (3)0.25685 (13)0.0171 (6)
C100.5550 (5)0.2447 (3)0.27298 (14)0.0199 (6)
H100.55980.30110.31090.024*
C110.7072 (5)0.2580 (3)0.23239 (13)0.0189 (6)
H110.81890.32260.24260.023*
O50.7268 (4)0.0224 (2)−0.03361 (11)0.0216 (5)
H5A0.763 (6)0.079 (5)−0.003 (2)0.046 (13)*
H5B0.815 (7)0.027 (5)−0.060 (2)0.049 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0176 (4)0.0143 (3)0.0154 (3)0.0017 (3)0.0016 (3)0.0006 (3)
N10.0216 (15)0.0139 (11)0.0326 (15)−0.0023 (10)−0.0021 (12)0.0047 (11)
N20.0213 (14)0.0133 (11)0.0152 (11)0.0014 (10)0.0005 (10)0.0005 (9)
N30.0253 (15)0.0227 (13)0.0231 (14)0.0026 (11)0.0061 (12)0.0037 (11)
O10.0175 (11)0.0213 (10)0.0203 (11)−0.0013 (9)−0.0007 (8)−0.0004 (9)
O20.0254 (12)0.0151 (10)0.0222 (11)0.0054 (8)0.0056 (9)0.0025 (8)
O30.0445 (16)0.0358 (13)0.0202 (11)−0.0024 (11)0.0134 (11)−0.0026 (10)
O40.0294 (15)0.0468 (15)0.0452 (16)−0.0171 (12)0.0146 (13)−0.0081 (13)
C10.0116 (15)0.0138 (12)0.0201 (14)−0.0010 (10)0.0029 (12)0.0012 (11)
C20.0251 (17)0.0172 (13)0.0184 (14)0.0024 (12)−0.0027 (13)−0.0017 (12)
C30.0309 (19)0.0169 (14)0.0292 (17)0.0010 (13)−0.0068 (14)−0.0050 (13)
C40.0158 (16)0.0244 (14)0.0211 (15)0.0013 (12)0.0026 (12)0.0048 (12)
C50.0135 (15)0.0199 (13)0.0196 (14)0.0005 (11)0.0037 (12)−0.0003 (12)
C60.0155 (15)0.0147 (12)0.0148 (13)0.0028 (11)0.0008 (11)0.0019 (11)
C70.0204 (16)0.0189 (13)0.0150 (13)0.0013 (12)−0.0024 (12)−0.0021 (11)
C80.0164 (16)0.0166 (13)0.0207 (14)0.0005 (11)−0.0012 (12)−0.0003 (12)
C90.0180 (15)0.0170 (13)0.0165 (14)0.0022 (11)0.0033 (12)0.0033 (11)
C100.0241 (17)0.0205 (13)0.0151 (13)0.0021 (12)0.0000 (12)−0.0035 (12)
C110.0221 (16)0.0190 (13)0.0156 (13)−0.0026 (12)−0.0008 (12)−0.0012 (11)
O50.0292 (14)0.0158 (10)0.0199 (11)−0.0026 (9)0.0037 (10)−0.0011 (9)
Geometric parameters (Å, º) top
S1—O11.444 (2)C4—C51.367 (4)
S1—O21.455 (2)C4—H40.9500
S1—N21.594 (2)C5—H50.9500
S1—C61.774 (3)C6—C111.390 (4)
N1—C31.337 (4)C6—C71.404 (4)
N1—C41.352 (4)C7—C81.381 (4)
N1—H1A0.92 (4)C7—H70.9500
N2—C11.370 (3)C8—C91.391 (4)
N3—O41.224 (4)C8—H80.9500
N3—O31.225 (3)C9—C101.385 (4)
N3—C91.468 (4)C10—C111.388 (4)
C1—C51.410 (4)C10—H100.9500
C1—C21.416 (4)C11—H110.9500
C2—C31.368 (4)O5—H5A0.85 (4)
C2—H20.9500O5—H5B0.85 (5)
C3—H30.9500
O1—S1—O2116.81 (13)C5—C4—H4119.8
O1—S1—N2113.86 (13)C4—C5—C1120.4 (3)
O2—S1—N2105.21 (12)C4—C5—H5119.8
O1—S1—C6106.69 (13)C1—C5—H5119.8
O2—S1—C6105.05 (13)C11—C6—C7120.9 (3)
N2—S1—C6108.69 (13)C11—C6—S1120.0 (2)
C3—N1—C4120.7 (3)C7—C6—S1119.1 (2)
C3—N1—H1A118 (3)C8—C7—C6119.8 (3)
C4—N1—H1A121 (3)C8—C7—H7120.1
C1—N2—S1122.1 (2)C6—C7—H7120.1
O4—N3—O3123.5 (3)C7—C8—C9118.2 (3)
O4—N3—C9118.3 (3)C7—C8—H8120.9
O3—N3—C9118.2 (3)C9—C8—H8120.9
N2—C1—C5115.9 (2)C10—C9—C8122.9 (3)
N2—C1—C2126.9 (3)C10—C9—N3118.4 (3)
C5—C1—C2117.2 (3)C8—C9—N3118.7 (3)
C3—C2—C1119.1 (3)C9—C10—C11118.5 (3)
C3—C2—H2120.5C9—C10—H10120.8
C1—C2—H2120.5C11—C10—H10120.8
N1—C3—C2122.0 (3)C10—C11—C6119.6 (3)
N1—C3—H3119.0C10—C11—H11120.2
C2—C3—H3119.0C6—C11—H11120.2
N1—C4—C5120.5 (3)H5A—O5—H5B109 (4)
N1—C4—H4119.8
O1—S1—N2—C1−36.5 (3)O2—S1—C6—C7−55.7 (3)
O2—S1—N2—C1−165.6 (2)N2—S1—C6—C756.5 (3)
C6—S1—N2—C182.3 (3)C11—C6—C7—C8−1.3 (4)
S1—N2—C1—C5164.4 (2)S1—C6—C7—C8177.6 (2)
S1—N2—C1—C2−16.8 (4)C6—C7—C8—C90.5 (4)
N2—C1—C2—C3178.6 (3)C7—C8—C9—C101.0 (4)
C5—C1—C2—C3−2.7 (5)C7—C8—C9—N3179.0 (3)
C4—N1—C3—C21.4 (5)O4—N3—C9—C10179.1 (3)
C1—C2—C3—N10.4 (5)O3—N3—C9—C100.6 (4)
C3—N1—C4—C5−0.6 (5)O4—N3—C9—C80.9 (4)
N1—C4—C5—C1−1.8 (5)O3—N3—C9—C8−177.6 (3)
N2—C1—C5—C4−177.7 (3)C8—C9—C10—C11−1.7 (4)
C2—C1—C5—C43.4 (4)N3—C9—C10—C11−179.8 (3)
O1—S1—C6—C11−1.5 (3)C9—C10—C11—C61.0 (4)
O2—S1—C6—C11123.1 (2)C7—C6—C11—C100.5 (4)
N2—S1—C6—C11−124.7 (2)S1—C6—C11—C10−178.3 (2)
O1—S1—C6—C7179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···N20.85 (4)1.97 (4)2.813 (3)167 (4)
O5—H5B···O2i0.85 (5)2.07 (5)2.895 (3)164 (4)
N1—H1A···O5ii0.92 (4)1.82 (4)2.728 (3)170 (4)
Symmetry codes: (i) −x+2, −y, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC11H9N3O4S·H2O
Mr297.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)6.7766 (14), 8.3932 (17), 21.717 (4)
β (°) 92.35 (3)
V (Å3)1234.2 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.932, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections		9708, 2908, 2022
Rint0.061
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.136, 1.17
No. of reflections2908
No. of parameters193
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.45

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···N20.85 (4)1.97 (4)2.813 (3)167 (4)
O5—H5B···O2i0.85 (5)2.07 (5)2.895 (3)164 (4)
N1—H1A···O5ii0.92 (4)1.82 (4)2.728 (3)170 (4)
Symmetry codes: (i) −x+2, −y, −z; (ii) x, y+1, z.
 

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. 1–19.  CrossRef Web of Science Google Scholar
 First citationDamiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735–2752.  Web of Science CrossRef PubMed CAS 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/MSC (2005). CrystalClear. Rigaku/MSC, 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Page o2109
doi:10.1107/S1600536808032273
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS