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organic compounds
4-(4-Nitrobenzenesulfonamido)pyridinium trichloroacetate
aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and bMedical College, Jiujiang University, Jiujiang 332000, People's Republic of China
*Correspondence e-mail: tju_zhoubin@yahoo.com.cn
In the title compound, C11H10N3O4S+·C2Cl3O2−, the benzene ring forms an angle of 85.21 (13)° with the pyridinium ring. The nitro group is nearly coplanar with its attached benzene ring [dihedral angle = 3.68 (12)°]. In the strong N—H⋯O hydrogen bonds link the ion-pairs. The packing is further consolidated by weak C—H⋯O interations.
Related literature
For the synthesis and structure of the unprotonated amine, see: Yu & Li (2007). For reference geometrical data, see: Allen et al. (1987
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997
); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997
); molecular graphics: SHELXTL (Bruker, 1997
); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S160053680706504X/hb2642sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706504X/hb2642Isup2.hkl
4-Nitro-(N-pyridyl)benzenesulfonamide was prepared by the method of Yu & Li (2007). Colourless blocks of (I) were grown by natural evaporation from a trichloroacetic acid solution of the amide.
The N-bound H atoms were located in a difference map and their positions were freely refined. The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding atoms. The constraint Uĩso~(H) = 1.2 U~eq~(C and N) was applied.
The title compound, (I), comprises of a pyridinium cation and a trichloroacetate anion (Fig. 1). In the cation, the short C—N distance [N2—C1 = 1.390 (3) Å] occurs between typical C=N (1.34–1.38 Å) and C—N (1.47–1.50 Å) bond lengths (Allen et al., 1987), indicative of significant double-bond character, despite of a strong electron-withdrawing sulfonyl group. The benzene ring forms an angle of 85.21 (13)° with the pyridinium ring. The nitro group is nearly coplanar and make an acute angle of 3.68 (12)° with the connected benzene ring.
The cation and anion are connected by a strong N—H···O hydrogen bond and weak C—H···O interactions (Table 1) complete the structure. Two short intramolecular C—H···O contacts also arise in the cation.
For the synthesis and structure of the unprotonated amine, see: Yu & Li (2007. For reference geometrical data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997). ![]() | Fig. 1. A view of (I) with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms). Hydrogen bonds are indicated by double-dashed lines. |
C11H10N3O4S+·C2Cl3O2− | F(000) = 896 |
Mr = 442.65 | Dx = 1.707 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2690 reflections |
a = 5.9929 (11) Å | θ = 2.5–25.7° |
b = 17.790 (3) Å | µ = 0.69 mm−1 |
c = 16.325 (3) Å | T = 294 K |
β = 98.377 (3)° | Block, colourless |
V = 1721.9 (6) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 4 |
Bruker SMART 1K CCD diffractometer | 3528 independent reflections |
Radiation source: fine-focus sealed tube | 2427 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.852, Tmax = 0.886 | k = −9→22 |
9742 measured reflections | l = −20→20 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0353P)2 + 0.9782P] where P = (Fo2 + 2Fc2)/3 |
3528 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C11H10N3O4S+·C2Cl3O2− | V = 1721.9 (6) Å3 |
Mr = 442.65 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.9929 (11) Å | µ = 0.69 mm−1 |
b = 17.790 (3) Å | T = 294 K |
c = 16.325 (3) Å | 0.24 × 0.22 × 0.18 mm |
β = 98.377 (3)° |
Bruker SMART 1K CCD diffractometer | 3528 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2427 reflections with I > 2σ(I) |
Tmin = 0.852, Tmax = 0.886 | Rint = 0.038 |
9742 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.37 e Å−3 |
3528 reflections | Δρmin = −0.38 e Å−3 |
241 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 | 0.20681 (12) | 0.30768 (4) | 0.84918 (4) | 0.03291 (18) | |
O1 | 0.2730 (4) | 0.26231 (11) | 0.92092 (11) | 0.0449 (5) | |
O2 | −0.0263 (3) | 0.32167 (11) | 0.82059 (13) | 0.0448 (5) | |
O3 | 0.8738 (4) | 0.60031 (12) | 0.95523 (13) | 0.0495 (5) | |
O4 | 0.5848 (4) | 0.65976 (12) | 0.89304 (15) | 0.0575 (6) | |
N1 | 0.2323 (4) | 0.30604 (14) | 0.52313 (15) | 0.0413 (6) | |
H1 | 0.215 (5) | 0.3155 (17) | 0.470 (2) | 0.050* | |
N2 | 0.3239 (4) | 0.26681 (13) | 0.77572 (13) | 0.0321 (5) | |
H2A | 0.422 (5) | 0.2386 (17) | 0.7939 (18) | 0.039* | |
N3 | 0.6823 (4) | 0.60178 (14) | 0.91655 (14) | 0.0372 (6) | |
C1 | 0.2886 (4) | 0.28291 (14) | 0.69149 (15) | 0.0270 (6) | |
C2 | 0.4432 (5) | 0.25395 (16) | 0.64290 (16) | 0.0358 (7) | |
H2 | 0.5671 | 0.2263 | 0.6673 | 0.043* | |
C3 | 0.4103 (5) | 0.26665 (16) | 0.55900 (17) | 0.0416 (7) | |
H3 | 0.5130 | 0.2476 | 0.5267 | 0.050* | |
C4 | 0.0846 (5) | 0.33458 (17) | 0.56820 (18) | 0.0430 (7) | |
H4 | −0.0383 | 0.3615 | 0.5418 | 0.052* | |
C5 | 0.1084 (5) | 0.32541 (16) | 0.65210 (17) | 0.0386 (7) | |
H5 | 0.0059 | 0.3472 | 0.6826 | 0.046* | |
C6 | 0.3464 (4) | 0.39542 (14) | 0.86639 (15) | 0.0284 (6) | |
C7 | 0.2334 (4) | 0.46213 (15) | 0.84301 (16) | 0.0320 (6) | |
H7 | 0.0850 | 0.4610 | 0.8166 | 0.038* | |
C8 | 0.3429 (4) | 0.53001 (15) | 0.85921 (16) | 0.0337 (6) | |
H8 | 0.2698 | 0.5751 | 0.8443 | 0.040* | |
C9 | 0.5640 (4) | 0.52928 (15) | 0.89817 (15) | 0.0299 (6) | |
C10 | 0.6797 (5) | 0.46378 (16) | 0.92142 (17) | 0.0347 (7) | |
H10 | 0.8285 | 0.4653 | 0.9474 | 0.042* | |
C11 | 0.5696 (4) | 0.39591 (15) | 0.90528 (16) | 0.0334 (6) | |
H11 | 0.6438 | 0.3510 | 0.9202 | 0.040* | |
O5 | 0.1076 (4) | 0.40196 (11) | 0.23515 (11) | 0.0457 (5) | |
O6 | 0.1360 (3) | 0.33610 (11) | 0.35309 (11) | 0.0412 (5) | |
Cl1 | 0.23049 (13) | 0.47867 (4) | 0.44855 (4) | 0.0447 (2) | |
Cl2 | 0.60598 (13) | 0.41336 (5) | 0.37668 (6) | 0.0579 (3) | |
Cl3 | 0.34546 (14) | 0.53626 (4) | 0.29679 (5) | 0.0486 (2) | |
C12 | 0.1730 (4) | 0.39111 (15) | 0.30852 (16) | 0.0293 (6) | |
C13 | 0.3314 (4) | 0.45299 (15) | 0.35494 (16) | 0.0305 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0421 (4) | 0.0312 (4) | 0.0291 (4) | −0.0018 (3) | 0.0176 (3) | −0.0008 (3) |
O1 | 0.0724 (15) | 0.0374 (12) | 0.0295 (10) | −0.0025 (10) | 0.0229 (10) | 0.0056 (9) |
O2 | 0.0358 (11) | 0.0469 (13) | 0.0559 (13) | −0.0052 (10) | 0.0205 (10) | −0.0086 (10) |
O3 | 0.0457 (13) | 0.0540 (14) | 0.0462 (12) | −0.0078 (11) | −0.0020 (10) | 0.0001 (11) |
O4 | 0.0529 (14) | 0.0316 (12) | 0.0862 (18) | 0.0019 (11) | 0.0046 (13) | 0.0025 (12) |
N1 | 0.0639 (18) | 0.0385 (14) | 0.0203 (11) | 0.0062 (13) | 0.0024 (12) | 0.0031 (11) |
N2 | 0.0416 (14) | 0.0330 (14) | 0.0230 (11) | 0.0110 (11) | 0.0088 (10) | 0.0022 (10) |
N3 | 0.0369 (14) | 0.0409 (15) | 0.0351 (13) | −0.0002 (12) | 0.0096 (11) | −0.0020 (11) |
C1 | 0.0348 (15) | 0.0230 (13) | 0.0241 (13) | −0.0013 (11) | 0.0072 (11) | −0.0008 (11) |
C2 | 0.0434 (17) | 0.0366 (16) | 0.0288 (15) | 0.0147 (13) | 0.0099 (12) | 0.0046 (13) |
C3 | 0.060 (2) | 0.0372 (17) | 0.0307 (16) | 0.0131 (15) | 0.0165 (15) | 0.0015 (13) |
C4 | 0.0457 (18) | 0.0436 (18) | 0.0369 (17) | 0.0128 (15) | −0.0032 (14) | 0.0050 (14) |
C5 | 0.0423 (17) | 0.0390 (17) | 0.0360 (16) | 0.0128 (14) | 0.0108 (13) | 0.0019 (13) |
C6 | 0.0334 (15) | 0.0285 (15) | 0.0259 (13) | 0.0022 (12) | 0.0134 (11) | 0.0004 (11) |
C7 | 0.0288 (15) | 0.0344 (16) | 0.0329 (15) | 0.0020 (12) | 0.0045 (12) | −0.0002 (12) |
C8 | 0.0333 (15) | 0.0310 (16) | 0.0374 (16) | 0.0080 (12) | 0.0069 (12) | 0.0031 (12) |
C9 | 0.0342 (15) | 0.0316 (15) | 0.0254 (13) | −0.0006 (12) | 0.0089 (12) | 0.0008 (11) |
C10 | 0.0301 (15) | 0.0429 (18) | 0.0312 (15) | 0.0028 (13) | 0.0046 (12) | 0.0045 (13) |
C11 | 0.0339 (15) | 0.0328 (16) | 0.0344 (15) | 0.0089 (13) | 0.0085 (12) | 0.0084 (12) |
O5 | 0.0601 (14) | 0.0476 (13) | 0.0255 (10) | −0.0095 (10) | −0.0068 (9) | 0.0008 (9) |
O6 | 0.0569 (13) | 0.0356 (11) | 0.0289 (10) | −0.0117 (10) | −0.0014 (9) | 0.0025 (9) |
Cl1 | 0.0561 (5) | 0.0464 (4) | 0.0335 (4) | −0.0041 (4) | 0.0126 (3) | −0.0148 (3) |
Cl2 | 0.0328 (4) | 0.0677 (6) | 0.0683 (6) | 0.0159 (4) | −0.0085 (4) | −0.0226 (5) |
Cl3 | 0.0610 (5) | 0.0360 (4) | 0.0514 (5) | −0.0091 (4) | 0.0168 (4) | 0.0002 (3) |
C12 | 0.0289 (14) | 0.0295 (15) | 0.0279 (14) | 0.0011 (12) | −0.0009 (11) | −0.0054 (12) |
C13 | 0.0279 (14) | 0.0339 (15) | 0.0291 (14) | 0.0019 (12) | 0.0020 (11) | −0.0071 (11) |
S1—O2 | 1.429 (2) | C4—H4 | 0.9300 |
S1—O1 | 1.430 (2) | C5—H5 | 0.9300 |
S1—N2 | 1.645 (2) | C6—C7 | 1.392 (3) |
S1—C6 | 1.774 (3) | C6—C11 | 1.395 (4) |
O3—N3 | 1.227 (3) | C7—C8 | 1.381 (4) |
O4—N3 | 1.220 (3) | C7—H7 | 0.9300 |
N1—C4 | 1.331 (4) | C8—C9 | 1.384 (4) |
N1—C3 | 1.338 (4) | C8—H8 | 0.9300 |
N1—H1 | 0.87 (3) | C9—C10 | 1.381 (4) |
N2—C1 | 1.390 (3) | C10—C11 | 1.383 (4) |
N2—H2A | 0.79 (3) | C10—H10 | 0.9300 |
N3—C9 | 1.481 (3) | C11—H11 | 0.9300 |
C1—C5 | 1.396 (4) | O5—C12 | 1.220 (3) |
C1—C2 | 1.402 (3) | O6—C12 | 1.258 (3) |
C2—C3 | 1.374 (4) | Cl1—C13 | 1.783 (3) |
C2—H2 | 0.9300 | Cl2—C13 | 1.778 (3) |
C3—H3 | 0.9300 | Cl3—C13 | 1.768 (3) |
C4—C5 | 1.366 (4) | C12—C13 | 1.574 (4) |
O2—S1—O1 | 120.47 (13) | C1—C5—H5 | 120.4 |
O2—S1—N2 | 109.85 (12) | C7—C6—C11 | 121.0 (2) |
O1—S1—N2 | 104.53 (12) | C7—C6—S1 | 120.5 (2) |
O2—S1—C6 | 108.34 (12) | C11—C6—S1 | 118.5 (2) |
O1—S1—C6 | 107.38 (12) | C8—C7—C6 | 119.6 (3) |
N2—S1—C6 | 105.25 (12) | C8—C7—H7 | 120.2 |
C4—N1—C3 | 120.6 (2) | C6—C7—H7 | 120.2 |
C4—N1—H1 | 119 (2) | C7—C8—C9 | 118.4 (2) |
C3—N1—H1 | 120 (2) | C7—C8—H8 | 120.8 |
C1—N2—S1 | 127.63 (19) | C9—C8—H8 | 120.8 |
C1—N2—H2A | 120 (2) | C10—C9—C8 | 122.9 (3) |
S1—N2—H2A | 112 (2) | C10—C9—N3 | 118.2 (2) |
O4—N3—O3 | 123.3 (3) | C8—C9—N3 | 118.9 (2) |
O4—N3—C9 | 118.6 (2) | C9—C10—C11 | 118.5 (3) |
O3—N3—C9 | 118.0 (2) | C9—C10—H10 | 120.7 |
N2—C1—C5 | 124.3 (2) | C11—C10—H10 | 120.7 |
N2—C1—C2 | 117.8 (2) | C10—C11—C6 | 119.5 (2) |
C5—C1—C2 | 118.0 (2) | C10—C11—H11 | 120.3 |
C3—C2—C1 | 119.5 (3) | C6—C11—H11 | 120.3 |
C3—C2—H2 | 120.2 | O5—C12—O6 | 129.2 (2) |
C1—C2—H2 | 120.2 | O5—C12—C13 | 116.5 (2) |
N1—C3—C2 | 120.8 (3) | O6—C12—C13 | 114.2 (2) |
N1—C3—H3 | 119.6 | C12—C13—Cl3 | 113.58 (18) |
C2—C3—H3 | 119.6 | C12—C13—Cl2 | 107.13 (17) |
N1—C4—C5 | 121.8 (3) | Cl3—C13—Cl2 | 108.93 (14) |
N1—C4—H4 | 119.1 | C12—C13—Cl1 | 109.61 (18) |
C5—C4—H4 | 119.1 | Cl3—C13—Cl1 | 107.11 (14) |
C4—C5—C1 | 119.2 (3) | Cl2—C13—Cl1 | 110.50 (14) |
C4—C5—H5 | 120.4 | ||
O2—S1—N2—C1 | 40.4 (3) | S1—C6—C7—C8 | 178.0 (2) |
O1—S1—N2—C1 | 171.0 (2) | C6—C7—C8—C9 | 0.3 (4) |
C6—S1—N2—C1 | −76.0 (3) | C7—C8—C9—C10 | 0.1 (4) |
S1—N2—C1—C5 | −15.4 (4) | C7—C8—C9—N3 | −179.4 (2) |
S1—N2—C1—C2 | 165.2 (2) | O4—N3—C9—C10 | 176.8 (2) |
N2—C1—C2—C3 | 178.0 (3) | O3—N3—C9—C10 | −3.5 (3) |
C5—C1—C2—C3 | −1.5 (4) | O4—N3—C9—C8 | −3.6 (4) |
C4—N1—C3—C2 | 0.8 (5) | O3—N3—C9—C8 | 176.0 (2) |
C1—C2—C3—N1 | −0.2 (4) | C8—C9—C10—C11 | −0.2 (4) |
C3—N1—C4—C5 | 0.4 (5) | N3—C9—C10—C11 | 179.3 (2) |
N1—C4—C5—C1 | −2.1 (5) | C9—C10—C11—C6 | −0.1 (4) |
N2—C1—C5—C4 | −176.8 (3) | C7—C6—C11—C10 | 0.5 (4) |
C2—C1—C5—C4 | 2.6 (4) | S1—C6—C11—C10 | −178.2 (2) |
O2—S1—C6—C7 | −7.4 (2) | O5—C12—C13—Cl3 | 11.0 (3) |
O1—S1—C6—C7 | −138.9 (2) | O6—C12—C13—Cl3 | −170.43 (19) |
N2—S1—C6—C7 | 110.1 (2) | O5—C12—C13—Cl2 | −109.3 (2) |
O2—S1—C6—C11 | 171.35 (19) | O6—C12—C13—Cl2 | 69.2 (3) |
O1—S1—C6—C11 | 39.8 (2) | O5—C12—C13—Cl1 | 130.8 (2) |
N2—S1—C6—C11 | −71.2 (2) | O6—C12—C13—Cl1 | −50.7 (3) |
C11—C6—C7—C8 | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.87 (3) | 1.93 (3) | 2.803 (3) | 172 (3) |
N2—H2A···O6i | 0.79 (3) | 2.00 (3) | 2.785 (3) | 171 (3) |
C2—H2···O5i | 0.93 | 2.53 | 3.240 (3) | 133 |
C3—H3···O1ii | 0.93 | 2.50 | 3.391 (4) | 162 |
C8—H8···O5iii | 0.93 | 2.47 | 3.149 (3) | 130 |
C10—H10···O3iv | 0.93 | 2.50 | 3.308 (4) | 146 |
C5—H5···O2 | 0.93 | 2.33 | 2.978 (4) | 126 |
C7—H7···O2 | 0.93 | 2.57 | 2.938 (3) | 104 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C11H10N3O4S+·C2Cl3O2− |
Mr | 442.65 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 5.9929 (11), 17.790 (3), 16.325 (3) |
β (°) | 98.377 (3) |
V (Å3) | 1721.9 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.852, 0.886 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9742, 3528, 2427 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.094, 1.01 |
No. of reflections | 3528 |
No. of parameters | 241 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.38 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.87 (3) | 1.93 (3) | 2.803 (3) | 172 (3) |
N2—H2A···O6i | 0.79 (3) | 2.00 (3) | 2.785 (3) | 171 (3) |
C2—H2···O5i | 0.93 | 2.53 | 3.240 (3) | 133 |
C3—H3···O1ii | 0.93 | 2.50 | 3.391 (4) | 162 |
C8—H8···O5iii | 0.93 | 2.47 | 3.149 (3) | 130 |
C10—H10···O3iv | 0.93 | 2.50 | 3.308 (4) | 146 |
C5—H5···O2 | 0.93 | 2.33 | 2.978 (4) | 126 |
C7—H7···O2 | 0.93 | 2.57 | 2.938 (3) | 104 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) −x+2, −y+1, −z+2. |
References
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The title compound, (I), comprises of a pyridinium cation and a trichloroacetate anion (Fig. 1). In the cation, the short C—N distance [N2—C1 = 1.390 (3) Å] occurs between typical C=N (1.34–1.38 Å) and C—N (1.47–1.50 Å) bond lengths (Allen et al., 1987), indicative of significant double-bond character, despite of a strong electron-withdrawing sulfonyl group. The benzene ring forms an angle of 85.21 (13)° with the pyridinium ring. The nitro group is nearly coplanar and make an acute angle of 3.68 (12)° with the connected benzene ring.
The cation and anion are connected by a strong N—H···O hydrogen bond and weak C—H···O interactions (Table 1) complete the structure. Two short intramolecular C—H···O contacts also arise in the cation.