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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o254.
Published online 2007 December 12. doi:  10.1107/S160053680706504X
PMCID: PMC2915311

4-(4-Nitro­benzene­sulfonamido)pyridinium trichloro­acetate

Abstract

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 crystal structure, 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 [triangle]). For reference geometrical data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-0o254-scheme1.jpg

Experimental

Crystal data

  • C11H10N3O4S+·C2Cl3O2
  • M r = 442.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o254-efi1.jpg
  • a = 5.9929 (11) Å
  • b = 17.790 (3) Å
  • c = 16.325 (3) Å
  • β = 98.377 (3)°
  • V = 1721.9 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.69 mm−1
  • T = 294 (2) K
  • 0.24 × 0.22 × 0.18 mm

Data collection

  • Bruker SMART 1K CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.852, T max = 0.886
  • 9742 measured reflections
  • 3528 independent reflections
  • 2427 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.094
  • S = 1.01
  • 3528 reflections
  • 241 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706504X/hb2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706504X/hb2642Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

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.

Figures

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.

Crystal data

C11H10N3O4S+·C2Cl3O2F000 = 896
Mr = 442.65Dx = 1.707 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2690 reflections
a = 5.9929 (11) Åθ = 2.5–25.7º
b = 17.790 (3) ŵ = 0.69 mm1
c = 16.325 (3) ÅT = 294 (2) K
β = 98.377 (3)ºBlock, colourless
V = 1721.9 (6) Å30.24 × 0.22 × 0.18 mm
Z = 4

Data collection

Bruker SMART 1K CCD diffractometer3528 independent reflections
Radiation source: fine-focus sealed tube2427 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
T = 294(2) Kθmax = 26.4º
ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.852, Tmax = 0.886k = −9→22
9742 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094  w = 1/[σ2(Fo2) + (0.0353P)2 + 0.9782P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3528 reflectionsΔρmax = 0.37 e Å3
241 parametersΔρmin = −0.38 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
S10.20681 (12)0.30768 (4)0.84918 (4)0.03291 (18)
O10.2730 (4)0.26231 (11)0.92092 (11)0.0449 (5)
O2−0.0263 (3)0.32167 (11)0.82059 (13)0.0448 (5)
O30.8738 (4)0.60031 (12)0.95523 (13)0.0495 (5)
O40.5848 (4)0.65976 (12)0.89304 (15)0.0575 (6)
N10.2323 (4)0.30604 (14)0.52313 (15)0.0413 (6)
H10.215 (5)0.3155 (17)0.470 (2)0.050*
N20.3239 (4)0.26681 (13)0.77572 (13)0.0321 (5)
H2A0.422 (5)0.2386 (17)0.7939 (18)0.039*
N30.6823 (4)0.60178 (14)0.91655 (14)0.0372 (6)
C10.2886 (4)0.28291 (14)0.69149 (15)0.0270 (6)
C20.4432 (5)0.25395 (16)0.64290 (16)0.0358 (7)
H20.56710.22630.66730.043*
C30.4103 (5)0.26665 (16)0.55900 (17)0.0416 (7)
H30.51300.24760.52670.050*
C40.0846 (5)0.33458 (17)0.56820 (18)0.0430 (7)
H4−0.03830.36150.54180.052*
C50.1084 (5)0.32541 (16)0.65210 (17)0.0386 (7)
H50.00590.34720.68260.046*
C60.3464 (4)0.39542 (14)0.86639 (15)0.0284 (6)
C70.2334 (4)0.46213 (15)0.84301 (16)0.0320 (6)
H70.08500.46100.81660.038*
C80.3429 (4)0.53001 (15)0.85921 (16)0.0337 (6)
H80.26980.57510.84430.040*
C90.5640 (4)0.52928 (15)0.89817 (15)0.0299 (6)
C100.6797 (5)0.46378 (16)0.92142 (17)0.0347 (7)
H100.82850.46530.94740.042*
C110.5696 (4)0.39591 (15)0.90528 (16)0.0334 (6)
H110.64380.35100.92020.040*
O50.1076 (4)0.40196 (11)0.23515 (11)0.0457 (5)
O60.1360 (3)0.33610 (11)0.35309 (11)0.0412 (5)
Cl10.23049 (13)0.47867 (4)0.44855 (4)0.0447 (2)
Cl20.60598 (13)0.41336 (5)0.37668 (6)0.0579 (3)
Cl30.34546 (14)0.53626 (4)0.29679 (5)0.0486 (2)
C120.1730 (4)0.39111 (15)0.30852 (16)0.0293 (6)
C130.3314 (4)0.45299 (15)0.35494 (16)0.0305 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0421 (4)0.0312 (4)0.0291 (4)−0.0018 (3)0.0176 (3)−0.0008 (3)
O10.0724 (15)0.0374 (12)0.0295 (10)−0.0025 (10)0.0229 (10)0.0056 (9)
O20.0358 (11)0.0469 (13)0.0559 (13)−0.0052 (10)0.0205 (10)−0.0086 (10)
O30.0457 (13)0.0540 (14)0.0462 (12)−0.0078 (11)−0.0020 (10)0.0001 (11)
O40.0529 (14)0.0316 (12)0.0862 (18)0.0019 (11)0.0046 (13)0.0025 (12)
N10.0639 (18)0.0385 (14)0.0203 (11)0.0062 (13)0.0024 (12)0.0031 (11)
N20.0416 (14)0.0330 (14)0.0230 (11)0.0110 (11)0.0088 (10)0.0022 (10)
N30.0369 (14)0.0409 (15)0.0351 (13)−0.0002 (12)0.0096 (11)−0.0020 (11)
C10.0348 (15)0.0230 (13)0.0241 (13)−0.0013 (11)0.0072 (11)−0.0008 (11)
C20.0434 (17)0.0366 (16)0.0288 (15)0.0147 (13)0.0099 (12)0.0046 (13)
C30.060 (2)0.0372 (17)0.0307 (16)0.0131 (15)0.0165 (15)0.0015 (13)
C40.0457 (18)0.0436 (18)0.0369 (17)0.0128 (15)−0.0032 (14)0.0050 (14)
C50.0423 (17)0.0390 (17)0.0360 (16)0.0128 (14)0.0108 (13)0.0019 (13)
C60.0334 (15)0.0285 (15)0.0259 (13)0.0022 (12)0.0134 (11)0.0004 (11)
C70.0288 (15)0.0344 (16)0.0329 (15)0.0020 (12)0.0045 (12)−0.0002 (12)
C80.0333 (15)0.0310 (16)0.0374 (16)0.0080 (12)0.0069 (12)0.0031 (12)
C90.0342 (15)0.0316 (15)0.0254 (13)−0.0006 (12)0.0089 (12)0.0008 (11)
C100.0301 (15)0.0429 (18)0.0312 (15)0.0028 (13)0.0046 (12)0.0045 (13)
C110.0339 (15)0.0328 (16)0.0344 (15)0.0089 (13)0.0085 (12)0.0084 (12)
O50.0601 (14)0.0476 (13)0.0255 (10)−0.0095 (10)−0.0068 (9)0.0008 (9)
O60.0569 (13)0.0356 (11)0.0289 (10)−0.0117 (10)−0.0014 (9)0.0025 (9)
Cl10.0561 (5)0.0464 (4)0.0335 (4)−0.0041 (4)0.0126 (3)−0.0148 (3)
Cl20.0328 (4)0.0677 (6)0.0683 (6)0.0159 (4)−0.0085 (4)−0.0226 (5)
Cl30.0610 (5)0.0360 (4)0.0514 (5)−0.0091 (4)0.0168 (4)0.0002 (3)
C120.0289 (14)0.0295 (15)0.0279 (14)0.0011 (12)−0.0009 (11)−0.0054 (12)
C130.0279 (14)0.0339 (15)0.0291 (14)0.0019 (12)0.0020 (11)−0.0071 (11)

Geometric parameters (Å, °)

S1—O21.429 (2)C4—H40.9300
S1—O11.430 (2)C5—H50.9300
S1—N21.645 (2)C6—C71.392 (3)
S1—C61.774 (3)C6—C111.395 (4)
O3—N31.227 (3)C7—C81.381 (4)
O4—N31.220 (3)C7—H70.9300
N1—C41.331 (4)C8—C91.384 (4)
N1—C31.338 (4)C8—H80.9300
N1—H10.87 (3)C9—C101.381 (4)
N2—C11.390 (3)C10—C111.383 (4)
N2—H2A0.79 (3)C10—H100.9300
N3—C91.481 (3)C11—H110.9300
C1—C51.396 (4)O5—C121.220 (3)
C1—C21.402 (3)O6—C121.258 (3)
C2—C31.374 (4)Cl1—C131.783 (3)
C2—H20.9300Cl2—C131.778 (3)
C3—H30.9300Cl3—C131.768 (3)
C4—C51.366 (4)C12—C131.574 (4)
O2—S1—O1120.47 (13)C1—C5—H5120.4
O2—S1—N2109.85 (12)C7—C6—C11121.0 (2)
O1—S1—N2104.53 (12)C7—C6—S1120.5 (2)
O2—S1—C6108.34 (12)C11—C6—S1118.5 (2)
O1—S1—C6107.38 (12)C8—C7—C6119.6 (3)
N2—S1—C6105.25 (12)C8—C7—H7120.2
C4—N1—C3120.6 (2)C6—C7—H7120.2
C4—N1—H1119 (2)C7—C8—C9118.4 (2)
C3—N1—H1120 (2)C7—C8—H8120.8
C1—N2—S1127.63 (19)C9—C8—H8120.8
C1—N2—H2A120 (2)C10—C9—C8122.9 (3)
S1—N2—H2A112 (2)C10—C9—N3118.2 (2)
O4—N3—O3123.3 (3)C8—C9—N3118.9 (2)
O4—N3—C9118.6 (2)C9—C10—C11118.5 (3)
O3—N3—C9118.0 (2)C9—C10—H10120.7
N2—C1—C5124.3 (2)C11—C10—H10120.7
N2—C1—C2117.8 (2)C10—C11—C6119.5 (2)
C5—C1—C2118.0 (2)C10—C11—H11120.3
C3—C2—C1119.5 (3)C6—C11—H11120.3
C3—C2—H2120.2O5—C12—O6129.2 (2)
C1—C2—H2120.2O5—C12—C13116.5 (2)
N1—C3—C2120.8 (3)O6—C12—C13114.2 (2)
N1—C3—H3119.6C12—C13—Cl3113.58 (18)
C2—C3—H3119.6C12—C13—Cl2107.13 (17)
N1—C4—C5121.8 (3)Cl3—C13—Cl2108.93 (14)
N1—C4—H4119.1C12—C13—Cl1109.61 (18)
C5—C4—H4119.1Cl3—C13—Cl1107.11 (14)
C4—C5—C1119.2 (3)Cl2—C13—Cl1110.50 (14)
C4—C5—H5120.4
O2—S1—N2—C140.4 (3)S1—C6—C7—C8178.0 (2)
O1—S1—N2—C1171.0 (2)C6—C7—C8—C90.3 (4)
C6—S1—N2—C1−76.0 (3)C7—C8—C9—C100.1 (4)
S1—N2—C1—C5−15.4 (4)C7—C8—C9—N3−179.4 (2)
S1—N2—C1—C2165.2 (2)O4—N3—C9—C10176.8 (2)
N2—C1—C2—C3178.0 (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—C20.8 (5)O3—N3—C9—C8176.0 (2)
C1—C2—C3—N1−0.2 (4)C8—C9—C10—C11−0.2 (4)
C3—N1—C4—C50.4 (5)N3—C9—C10—C11179.3 (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—C100.5 (4)
C2—C1—C5—C42.6 (4)S1—C6—C11—C10−178.2 (2)
O2—S1—C6—C7−7.4 (2)O5—C12—C13—Cl311.0 (3)
O1—S1—C6—C7−138.9 (2)O6—C12—C13—Cl3−170.43 (19)
N2—S1—C6—C7110.1 (2)O5—C12—C13—Cl2−109.3 (2)
O2—S1—C6—C11171.35 (19)O6—C12—C13—Cl269.2 (3)
O1—S1—C6—C1139.8 (2)O5—C12—C13—Cl1130.8 (2)
N2—S1—C6—C11−71.2 (2)O6—C12—C13—Cl1−50.7 (3)
C11—C6—C7—C8−0.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O60.87 (3)1.93 (3)2.803 (3)172 (3)
N2—H2A···O6i0.79 (3)2.00 (3)2.785 (3)171 (3)
C2—H2···O5i0.932.533.240 (3)133
C3—H3···O1ii0.932.503.391 (4)162
C8—H8···O5iii0.932.473.149 (3)130
C10—H10···O3iv0.932.503.308 (4)146
C5—H5···O20.932.332.978 (4)126
C7—H7···O20.932.572.938 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2642).

References

  • 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.
  • Bruker (1997). SMART, SAINT and SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Yu, H.-J. & Li, J.-S. (2007). Acta Cryst. E63, o3399.

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