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organic compounds
4-(4-Nitrobenzenesulfonamido)pyridinium chloride
aDepartment 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, and cCollege of Plant Protection, Henan Agricultural University, Zhengzhou 450052, People's Republic of China
*Correspondence e-mail: mohz@yahoo.cn
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 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
|
Refinement
|
|
Data collection: CrystalClear (Rigaku/MSC, 2005); cell 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.
Supporting information
10.1107/S1600536808032054/zl2146sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808032054/zl2146Isup2.hkl
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%.
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).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
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).C11H10N3O4S+·Cl− | F(000) = 1296 |
Mr = 315.73 | Dx = 1.614 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 37.942 (8) Å | Cell parameters from 3179 reflections |
b = 5.2446 (10) Å | θ = 2.6–27.1° |
c = 13.713 (3) Å | µ = 0.47 mm−1 |
β = 107.77 (3)° | T = 113 K |
V = 2598.5 (9) Å3 | Block, colourless |
Z = 8 | 0.12 × 0.10 × 0.08 mm |
Rigaku Saturn CCD area-detector diffractometer | 2865 independent reflections |
Radiation source: Rotating anode | 2330 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.043 |
Detector resolution: 7.21 pixels mm-1 | θmax = 27.1°, θmin = 2.3° |
ω and ϕ scans | h = −35→48 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −6→6 |
Tmin = 0.932, Tmax = 0.963 | l = −17→13 |
9693 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0506P)2 + 1.967P] where P = (Fo2 + 2Fc2)/3 |
2865 reflections | (Δ/σ)max = 0.001 |
189 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C11H10N3O4S+·Cl− | V = 2598.5 (9) Å3 |
Mr = 315.73 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 37.942 (8) Å | µ = 0.47 mm−1 |
b = 5.2446 (10) Å | T = 113 K |
c = 13.713 (3) Å | 0.12 × 0.10 × 0.08 mm |
β = 107.77 (3)° |
Rigaku Saturn CCD area-detector diffractometer | 2865 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 2330 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.963 | Rint = 0.043 |
9693 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.39 e Å−3 |
2865 reflections | Δρmin = −0.48 e Å−3 |
189 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.130148 (12) | 0.37275 (10) | 0.40268 (4) | 0.02104 (16) | |
O1 | 0.12396 (4) | 0.1690 (3) | 0.32996 (12) | 0.0268 (4) | |
O2 | 0.14305 (4) | 0.3226 (3) | 0.51052 (12) | 0.0271 (4) | |
O3 | 0.21998 (4) | 1.2270 (3) | 0.21517 (12) | 0.0320 (4) | |
O4 | 0.25562 (4) | 1.2246 (3) | 0.37259 (12) | 0.0334 (4) | |
N1 | 0.05555 (5) | 1.1001 (4) | 0.52726 (16) | 0.0297 (5) | |
N2 | 0.09049 (4) | 0.5214 (4) | 0.37499 (15) | 0.0215 (4) | |
N3 | 0.22877 (5) | 1.1462 (3) | 0.30326 (14) | 0.0246 (4) | |
C1 | 0.08046 (5) | 0.7177 (4) | 0.42979 (16) | 0.0217 (4) | |
C2 | 0.10010 (6) | 0.7864 (4) | 0.52953 (17) | 0.0253 (5) | |
H2 | 0.1227 | 0.7032 | 0.5645 | 0.030* | |
C3 | 0.08643 (6) | 0.9760 (4) | 0.57664 (18) | 0.0284 (5) | |
H3 | 0.0992 | 1.0196 | 0.6456 | 0.034* | |
C4 | 0.03605 (6) | 1.0410 (5) | 0.43021 (19) | 0.0323 (5) | |
H4 | 0.0141 | 1.1327 | 0.3966 | 0.039* | |
C5 | 0.04777 (5) | 0.8496 (4) | 0.38013 (18) | 0.0277 (5) | |
H5 | 0.0338 | 0.8060 | 0.3120 | 0.033* | |
C6 | 0.16110 (5) | 0.5922 (4) | 0.37472 (16) | 0.0190 (4) | |
C7 | 0.15830 (5) | 0.6369 (4) | 0.27247 (16) | 0.0221 (5) | |
H7 | 0.1409 | 0.5446 | 0.2196 | 0.027* | |
C8 | 0.18104 (5) | 0.8169 (4) | 0.24842 (16) | 0.0225 (4) | |
H8 | 0.1797 | 0.8499 | 0.1793 | 0.027* | |
C9 | 0.20570 (5) | 0.9469 (4) | 0.32797 (16) | 0.0196 (4) | |
C10 | 0.20940 (5) | 0.9012 (4) | 0.43010 (16) | 0.0229 (5) | |
H10 | 0.2272 | 0.9914 | 0.4827 | 0.028* | |
C11 | 0.18659 (5) | 0.7207 (4) | 0.45380 (16) | 0.0223 (4) | |
H11 | 0.1884 | 0.6856 | 0.5231 | 0.027* | |
Cl1 | 0.038070 (13) | 0.52540 (11) | 0.65583 (4) | 0.02598 (16) | |
H1 | 0.0477 (8) | 1.233 (6) | 0.561 (2) | 0.058 (9)* | |
H2A | 0.0771 (8) | 0.504 (6) | 0.310 (2) | 0.059 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0197 (2) | 0.0190 (3) | 0.0238 (3) | 0.00150 (18) | 0.00570 (19) | 0.0027 (2) |
O1 | 0.0272 (7) | 0.0204 (8) | 0.0333 (9) | 0.0011 (6) | 0.0101 (6) | −0.0028 (7) |
O2 | 0.0281 (7) | 0.0289 (9) | 0.0233 (9) | 0.0018 (6) | 0.0062 (6) | 0.0100 (7) |
O3 | 0.0388 (8) | 0.0284 (9) | 0.0310 (10) | −0.0013 (7) | 0.0137 (7) | 0.0059 (8) |
O4 | 0.0313 (8) | 0.0372 (10) | 0.0321 (10) | −0.0125 (7) | 0.0103 (7) | −0.0109 (8) |
N1 | 0.0333 (10) | 0.0246 (11) | 0.0368 (12) | −0.0034 (8) | 0.0190 (9) | −0.0056 (9) |
N2 | 0.0189 (8) | 0.0234 (10) | 0.0207 (10) | 0.0006 (7) | 0.0038 (7) | −0.0008 (8) |
N3 | 0.0261 (8) | 0.0216 (10) | 0.0287 (11) | −0.0001 (7) | 0.0124 (7) | −0.0033 (8) |
C1 | 0.0194 (9) | 0.0231 (11) | 0.0246 (11) | −0.0038 (8) | 0.0097 (8) | 0.0007 (9) |
C2 | 0.0272 (10) | 0.0249 (12) | 0.0236 (12) | −0.0005 (8) | 0.0074 (8) | 0.0023 (10) |
C3 | 0.0326 (11) | 0.0301 (13) | 0.0249 (12) | −0.0068 (9) | 0.0126 (9) | −0.0016 (10) |
C4 | 0.0261 (10) | 0.0329 (14) | 0.0392 (15) | 0.0050 (9) | 0.0117 (10) | −0.0031 (11) |
C5 | 0.0209 (9) | 0.0322 (13) | 0.0281 (13) | 0.0016 (8) | 0.0046 (8) | −0.0034 (10) |
C6 | 0.0185 (8) | 0.0186 (11) | 0.0195 (11) | 0.0033 (7) | 0.0055 (7) | 0.0012 (8) |
C7 | 0.0227 (9) | 0.0222 (12) | 0.0205 (11) | 0.0000 (8) | 0.0050 (8) | −0.0036 (9) |
C8 | 0.0260 (9) | 0.0239 (12) | 0.0183 (11) | 0.0013 (8) | 0.0081 (8) | −0.0001 (9) |
C9 | 0.0181 (8) | 0.0205 (11) | 0.0213 (11) | 0.0009 (7) | 0.0078 (7) | −0.0003 (9) |
C10 | 0.0193 (9) | 0.0277 (12) | 0.0197 (11) | 0.0008 (8) | 0.0030 (8) | −0.0008 (9) |
C11 | 0.0206 (9) | 0.0275 (12) | 0.0176 (11) | 0.0011 (8) | 0.0041 (7) | 0.0013 (9) |
Cl1 | 0.0256 (3) | 0.0283 (3) | 0.0228 (3) | 0.00156 (19) | 0.0056 (2) | −0.0007 (2) |
S1—O1 | 1.4311 (16) | C2—H2 | 0.9500 |
S1—O2 | 1.4331 (16) | C3—H3 | 0.9500 |
S1—N2 | 1.6332 (17) | C4—C5 | 1.365 (3) |
S1—C6 | 1.768 (2) | C4—H4 | 0.9500 |
O3—N3 | 1.226 (2) | C5—H5 | 0.9500 |
O4—N3 | 1.233 (2) | C6—C11 | 1.388 (3) |
N1—C3 | 1.330 (3) | C6—C7 | 1.393 (3) |
N1—C4 | 1.347 (3) | C7—C8 | 1.385 (3) |
N1—H1 | 0.93 (3) | C7—H7 | 0.9500 |
N2—C1 | 1.394 (3) | C8—C9 | 1.381 (3) |
N2—H2A | 0.89 (3) | C8—H8 | 0.9500 |
N3—C9 | 1.468 (3) | C9—C10 | 1.385 (3) |
C1—C2 | 1.391 (3) | C10—C11 | 1.387 (3) |
C1—C5 | 1.402 (3) | C10—H10 | 0.9500 |
C2—C3 | 1.371 (3) | C11—H11 | 0.9500 |
O1—S1—O2 | 120.92 (10) | N1—C4—C5 | 120.1 (2) |
O1—S1—N2 | 104.52 (10) | N1—C4—H4 | 120.0 |
O2—S1—N2 | 109.13 (10) | C5—C4—H4 | 120.0 |
O1—S1—C6 | 108.27 (10) | C4—C5—C1 | 119.6 (2) |
O2—S1—C6 | 107.63 (10) | C4—C5—H5 | 120.2 |
N2—S1—C6 | 105.35 (9) | C1—C5—H5 | 120.2 |
C3—N1—C4 | 121.6 (2) | C11—C6—C7 | 121.73 (19) |
C3—N1—H1 | 118.5 (18) | C11—C6—S1 | 119.82 (16) |
C4—N1—H1 | 119.9 (18) | C7—C6—S1 | 118.42 (15) |
C1—N2—S1 | 127.65 (15) | C8—C7—C6 | 119.50 (19) |
C1—N2—H2A | 117 (2) | C8—C7—H7 | 120.3 |
S1—N2—H2A | 112.8 (19) | C6—C7—H7 | 120.3 |
O3—N3—O4 | 123.83 (19) | C9—C8—C7 | 118.0 (2) |
O3—N3—C9 | 118.12 (18) | C9—C8—H8 | 121.0 |
O4—N3—C9 | 118.04 (18) | C7—C8—H8 | 121.0 |
C2—C1—N2 | 124.68 (19) | C8—C9—C10 | 123.26 (19) |
C2—C1—C5 | 118.6 (2) | C8—C9—N3 | 118.51 (19) |
N2—C1—C5 | 116.69 (19) | C10—C9—N3 | 118.22 (18) |
C3—C2—C1 | 119.0 (2) | C9—C10—C11 | 118.50 (19) |
C3—C2—H2 | 120.5 | C9—C10—H10 | 120.8 |
C1—C2—H2 | 120.5 | C11—C10—H10 | 120.8 |
N1—C3—C2 | 121.1 (2) | C10—C11—C6 | 118.97 (19) |
N1—C3—H3 | 119.5 | C10—C11—H11 | 120.5 |
C2—C3—H3 | 119.5 | C6—C11—H11 | 120.5 |
O1—S1—N2—C1 | 172.50 (18) | O2—S1—C6—C7 | 168.84 (15) |
O2—S1—N2—C1 | 41.8 (2) | N2—S1—C6—C7 | −74.81 (18) |
C6—S1—N2—C1 | −73.5 (2) | C11—C6—C7—C8 | −1.0 (3) |
S1—N2—C1—C2 | −14.1 (3) | S1—C6—C7—C8 | 176.94 (15) |
S1—N2—C1—C5 | 167.25 (16) | C6—C7—C8—C9 | −0.4 (3) |
N2—C1—C2—C3 | −177.14 (19) | C7—C8—C9—C10 | 1.8 (3) |
C5—C1—C2—C3 | 1.5 (3) | C7—C8—C9—N3 | −177.26 (17) |
C4—N1—C3—C2 | 1.5 (3) | O3—N3—C9—C8 | 15.3 (3) |
C1—C2—C3—N1 | −2.4 (3) | O4—N3—C9—C8 | −165.44 (18) |
C3—N1—C4—C5 | 0.1 (3) | O3—N3—C9—C10 | −163.75 (18) |
N1—C4—C5—C1 | −1.0 (4) | O4—N3—C9—C10 | 15.5 (3) |
C2—C1—C5—C4 | 0.1 (3) | C8—C9—C10—C11 | −1.7 (3) |
N2—C1—C5—C4 | 178.9 (2) | N3—C9—C10—C11 | 177.29 (17) |
O1—S1—C6—C11 | −145.42 (16) | C9—C10—C11—C6 | 0.3 (3) |
O2—S1—C6—C11 | −13.15 (19) | C7—C6—C11—C10 | 1.1 (3) |
N2—S1—C6—C11 | 103.20 (18) | S1—C6—C11—C10 | −176.88 (15) |
O1—S1—C6—C7 | 36.57 (18) |
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) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H10N3O4S+·Cl− |
Mr | 315.73 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 113 |
a, b, c (Å) | 37.942 (8), 5.2446 (10), 13.713 (3) |
β (°) | 107.77 (3) |
V (Å3) | 2598.5 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.12 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Rigaku Saturn CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.932, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9693, 2865, 2330 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.107, 1.06 |
No. of reflections | 2865 |
No. of parameters | 189 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.48 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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) |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z−1/2. |
References
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. CrossRef Web of Science Google Scholar
Damiano, T., Morton, D. & Nelson, A. (2007). Org. Biomol. Chem. 5, 2735—2752. Web of Science CrossRef Google Scholar
Li, J.-S., Chen, L.-G., Zhang, Y.-Y., Xu, Y.-J., Deng, Y. & Huang, P.-M. (2007). J. Chem. Res. pp. 350–352. CrossRef Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399. CSD CrossRef IUCr Journals Google Scholar
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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.