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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1885.
Published online 2008 September 6. doi:  10.1107/S1600536808027499
PMCID: PMC2959441

N-(2-Nitro­phenyl­sulfon­yl)-N-(4-nitro­phenyl­sulfon­yl)methyl­amine

Abstract

In the crystal structure of the title compound, C13H11N3O8S2, mol­ecules are linked by inter­molecular C—H(...)O hydrogen bonds into zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π–π stacking inter­actions [centroid–centroid distance = 3.749 (3) Å] involving adjacent 4-nitro­benzene rings. Intra­molecular C—H(...)O hydrogen bonds are also present.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 [triangle]); Curtis & Pavkovic (1983 [triangle]). For details of the biological activities of sulfonamide compounds, see: Kamoshita et al. (1987 [triangle]). For details of the application of sulfonimade catalysts, see: Zhang et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1885-scheme1.jpg

Experimental

Crystal data

  • C13H11N3O8S2
  • M r = 401.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1885-efi1.jpg
  • a = 13.517 (3) Å
  • b = 9.994 (2) Å
  • c = 11.990 (2) Å
  • β = 95.26 (3)°
  • V = 1613.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.38 mm−1
  • T = 153 (2) K
  • 0.58 × 0.47 × 0.29 mm

Data collection

  • Rigaku R-AXIS RAPID IP area-detector diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi 1995 [triangle]) T min = 0.750, T max = 0.897
  • 15376 measured reflections
  • 3683 independent reflections
  • 3540 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.094
  • S = 1.13
  • 3683 reflections
  • 236 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027499/rz2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027499/rz2239Isup2.hkl

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

supplementary crystallographic information

Comment

Molecules containing the sulfonimide group have been recently of interest for their applications as herbicides (Kamoshita et al., 1987) and catalysts (Zhang et al., 2007). In the present paper, the crystal structure of a new compound containing two sulfonimide groups is reported.

In the molecule of the title compound (Fig. 1) all bond lengths are normal (Allen et al., 1987) and in a good agreement with those reported previously for similar compounds (Henschel et al., 1996; Curtis & Pavkovic, 1983). The molecular conformation is stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal structure, molecules are linked by intermolecular C—H···O hydrogen bonding interactions (Fig. 2) forming zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π-π stacking interactions occurring between adjacent the 4-nitrobenzene rings with a centroid-centroid distance of 3.749 (3) Å.

Experimental

A solution of 4-nitro-benzene-1-sulfonyl chloride (10 mmol, 2.21 g) in anhydrous CH2Cl2 (10 mL) was dropwise added over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (10 mmol, 2.16 g) and EtN(i-Pr)2 (3 mmol) in CH2Cl2 (10 mL) at 273K. The mixture was stirred at room temperature for 4 h. The organic phase was washed with 2N HCl twice and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography (2:1 cyclohexane/dichloromethane) to give the title compound as a white solid (2.81 mg, 70% yield). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/dichloromethane solution (1:1 v/v) at room temperature.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 or 0.98 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
Packing diagram of the title compound viewed down the b axis, showing the chains of molecules formed by intermolecular hydrogen bonds (dashed lines).

Crystal data

C13H11N3O8S2F(000) = 824
Mr = 401.37Dx = 1.653 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10014 reflections
a = 13.517 (3) Åθ = 6.2–55.0°
b = 9.994 (2) ŵ = 0.38 mm1
c = 11.990 (2) ÅT = 153 K
β = 95.26 (3)°Block, colourless
V = 1613.0 (6) Å30.58 × 0.47 × 0.29 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer3683 independent reflections
Radiation source: Rotating Anode3540 reflections with I > 2σ(I)
graphiteRint = 0.017
ω oscillation scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi 1995)h = −17→17
Tmin = 0.750, Tmax = 0.897k = −12→12
15376 measured reflectionsl = −15→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.094w = 1/[σ2(Fo2) + (0.0558P)2 + 0.7411P] where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
3683 reflectionsΔρmax = 0.49 e Å3
236 parametersΔρmin = −0.41 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0231 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.15312 (2)0.15728 (3)0.41897 (3)0.01644 (11)
S20.35222 (2)0.06267 (3)0.48921 (3)0.01728 (11)
O80.20741 (8)0.19778 (11)0.32804 (8)0.0220 (2)
O70.06390 (8)0.08053 (11)0.39952 (9)0.0241 (2)
O30.13493 (10)0.70583 (13)0.72576 (12)0.0399 (3)
O60.39404 (8)−0.02832 (12)0.57283 (9)0.0261 (2)
O50.38943 (8)0.19667 (11)0.48792 (9)0.0255 (2)
O4−0.01529 (9)0.63329 (11)0.73325 (9)0.0271 (2)
N30.23085 (9)0.06608 (12)0.50391 (10)0.0187 (2)
C70.12748 (10)0.29709 (13)0.50127 (11)0.0161 (3)
O20.34613 (11)−0.36035 (12)0.39097 (13)0.0401 (3)
C80.04276 (10)0.29488 (13)0.55885 (11)0.0173 (3)
H8B−0.00110.22050.55230.021*
N10.31903 (10)−0.24388 (12)0.39825 (11)0.0241 (3)
C60.36282 (10)−0.14363 (14)0.32761 (12)0.0199 (3)
C110.17430 (11)0.51236 (14)0.57559 (13)0.0215 (3)
H11A0.21800.58700.58260.026*
C120.19373 (10)0.40442 (15)0.50825 (12)0.0209 (3)
H12A0.25090.40360.46770.025*
C40.40219 (10)0.08068 (15)0.27685 (13)0.0218 (3)
H4A0.40430.17390.29220.026*
C100.08951 (10)0.50856 (13)0.63249 (11)0.0177 (3)
C50.36741 (10)−0.00693 (14)0.35469 (11)0.0174 (3)
O10.25661 (11)−0.20743 (12)0.45856 (12)0.0375 (3)
C90.02324 (10)0.40325 (14)0.62611 (11)0.0181 (3)
H9A−0.03400.40480.66650.022*
C30.43385 (11)0.03367 (18)0.17699 (13)0.0269 (3)
H3A0.45610.09490.12410.032*
N20.06833 (10)0.62403 (12)0.70259 (10)0.0227 (3)
C20.43303 (12)−0.10224 (18)0.15451 (13)0.0286 (3)
H2A0.4578−0.13450.08790.034*
C130.19287 (12)0.00944 (17)0.60575 (13)0.0268 (3)
H13A0.12050.01960.60110.040*
H13B0.22290.05690.67190.040*
H13C0.2100−0.08570.61170.040*
C10.39611 (11)−0.19141 (16)0.22913 (13)0.0258 (3)
H1A0.3937−0.28440.21290.031*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01570 (18)0.01769 (18)0.01585 (18)0.00236 (11)0.00106 (12)−0.00261 (11)
S20.01591 (17)0.01766 (18)0.01801 (18)0.00156 (11)0.00017 (12)−0.00121 (11)
O80.0226 (5)0.0266 (5)0.0172 (5)0.0065 (4)0.0044 (4)0.0012 (4)
O70.0198 (5)0.0260 (5)0.0260 (5)−0.0025 (4)0.0002 (4)−0.0080 (4)
O30.0363 (7)0.0304 (6)0.0522 (8)−0.0013 (5)−0.0003 (6)−0.0206 (6)
O60.0242 (5)0.0314 (6)0.0221 (5)0.0076 (4)−0.0012 (4)0.0041 (4)
O50.0255 (5)0.0213 (5)0.0295 (6)−0.0048 (4)0.0017 (4)−0.0063 (4)
O40.0322 (6)0.0265 (5)0.0234 (5)0.0113 (4)0.0059 (4)−0.0020 (4)
N30.0179 (5)0.0196 (6)0.0193 (6)0.0046 (4)0.0050 (4)0.0025 (4)
C70.0167 (6)0.0158 (6)0.0156 (6)0.0036 (5)0.0007 (5)−0.0003 (5)
O20.0495 (8)0.0169 (5)0.0556 (8)0.0060 (5)0.0141 (6)0.0020 (5)
C80.0185 (6)0.0170 (6)0.0167 (6)0.0008 (5)0.0020 (5)0.0019 (5)
N10.0279 (6)0.0172 (6)0.0270 (6)−0.0001 (5)0.0015 (5)−0.0007 (5)
C60.0175 (6)0.0200 (7)0.0220 (7)0.0020 (5)0.0012 (5)−0.0002 (5)
C110.0195 (6)0.0173 (6)0.0276 (7)−0.0006 (5)0.0010 (5)−0.0013 (5)
C120.0167 (6)0.0207 (7)0.0260 (7)0.0005 (5)0.0054 (5)−0.0011 (5)
C40.0162 (6)0.0240 (7)0.0253 (7)−0.0002 (5)0.0032 (5)0.0026 (5)
C100.0215 (6)0.0158 (6)0.0154 (6)0.0060 (5)−0.0017 (5)−0.0004 (5)
C50.0135 (6)0.0193 (6)0.0193 (6)0.0021 (5)0.0018 (5)−0.0010 (5)
O10.0488 (7)0.0227 (6)0.0449 (7)−0.0002 (5)0.0257 (6)0.0008 (5)
C90.0200 (6)0.0196 (6)0.0152 (6)0.0038 (5)0.0034 (5)0.0025 (5)
C30.0198 (7)0.0379 (8)0.0233 (7)−0.0007 (6)0.0046 (6)0.0046 (6)
N20.0296 (6)0.0184 (6)0.0192 (6)0.0071 (5)−0.0021 (5)−0.0021 (5)
C20.0227 (7)0.0422 (9)0.0214 (7)0.0056 (6)0.0044 (6)−0.0045 (6)
C130.0280 (7)0.0300 (8)0.0237 (7)0.0051 (6)0.0097 (6)0.0079 (6)
C10.0237 (7)0.0272 (7)0.0263 (7)0.0051 (6)0.0005 (6)−0.0076 (6)

Geometric parameters (Å, °)

S1—O81.4275 (11)C6—C51.4044 (19)
S1—O71.4304 (11)C11—C121.387 (2)
S1—N31.6660 (13)C11—C101.387 (2)
S1—C71.7633 (14)C11—H11A0.9500
S2—O61.4310 (11)C12—H12A0.9500
S2—O51.4312 (11)C4—C31.390 (2)
S2—N31.6665 (13)C4—C51.393 (2)
S2—C51.7855 (14)C4—H4A0.9500
O3—N21.2289 (19)C10—C91.380 (2)
O4—N21.2236 (18)C10—N21.4712 (17)
N3—C131.4799 (18)C9—H9A0.9500
C7—C81.3905 (19)C3—C21.385 (2)
C7—C121.3950 (19)C3—H3A0.9500
O2—N11.2258 (17)C2—C11.388 (2)
C8—C91.3901 (19)C2—H2A0.9500
C8—H8B0.9500C13—H13A0.9800
N1—O11.2164 (18)C13—H13B0.9800
N1—C61.4709 (19)C13—H13C0.9800
C6—C11.387 (2)C1—H1A0.9500
O8—S1—O7120.82 (7)C7—C12—H12A120.7
O8—S1—N3106.41 (6)C3—C4—C5120.96 (14)
O7—S1—N3106.34 (7)C3—C4—H4A119.5
O8—S1—C7110.12 (7)C5—C4—H4A119.5
O7—S1—C7108.07 (7)C9—C10—C11123.72 (13)
N3—S1—C7103.69 (6)C9—C10—N2118.08 (13)
O6—S2—O5119.05 (7)C11—C10—N2118.20 (13)
O6—S2—N3105.57 (7)C4—C5—C6117.85 (13)
O5—S2—N3109.41 (6)C4—C5—S2115.74 (11)
O6—S2—C5108.34 (7)C6—C5—S2125.56 (11)
O5—S2—C5106.57 (7)C10—C9—C8118.02 (13)
N3—S2—C5107.42 (7)C10—C9—H9A121.0
C13—N3—S1117.82 (10)C8—C9—H9A121.0
C13—N3—S2119.92 (10)C2—C3—C4120.11 (15)
S1—N3—S2121.22 (7)C2—C3—H3A119.9
C8—C7—C12122.40 (12)C4—C3—H3A119.9
C8—C7—S1118.58 (10)O4—N2—O3124.02 (13)
C12—C7—S1119.00 (10)O4—N2—C10117.68 (12)
C9—C8—C7118.98 (13)O3—N2—C10118.30 (13)
C9—C8—H8B120.5C3—C2—C1120.10 (14)
C7—C8—H8B120.5C3—C2—H2A120.0
O1—N1—O2123.70 (14)C1—C2—H2A120.0
O1—N1—C6118.43 (12)N3—C13—H13A109.5
O2—N1—C6117.85 (13)N3—C13—H13B109.5
C1—C6—C5121.40 (14)H13A—C13—H13B109.5
C1—C6—N1115.78 (13)N3—C13—H13C109.5
C5—C6—N1122.76 (13)H13A—C13—H13C109.5
C12—C11—C10118.30 (13)H13B—C13—H13C109.5
C12—C11—H11A120.8C6—C1—C2119.47 (15)
C10—C11—H11A120.8C6—C1—H1A120.3
C11—C12—C7118.57 (13)C2—C1—H1A120.3
C11—C12—H12A120.7
O8—S1—N3—C13−179.35 (11)C12—C11—C10—C90.1 (2)
O7—S1—N3—C13−49.34 (12)C12—C11—C10—N2−179.14 (12)
C7—S1—N3—C1364.50 (12)C3—C4—C5—C6−1.7 (2)
O8—S1—N3—S212.32 (10)C3—C4—C5—S2168.34 (11)
O7—S1—N3—S2142.33 (8)C1—C6—C5—C43.0 (2)
C7—S1—N3—S2−103.84 (9)N1—C6—C5—C4−174.28 (13)
O6—S2—N3—C1313.90 (13)C1—C6—C5—S2−165.97 (11)
O5—S2—N3—C13−115.35 (12)N1—C6—C5—S216.74 (19)
C5—S2—N3—C13129.34 (12)O6—S2—C5—C4−134.24 (11)
O6—S2—N3—S1−178.01 (8)O5—S2—C5—C4−5.02 (12)
O5—S2—N3—S152.74 (10)N3—S2—C5—C4112.16 (11)
C5—S2—N3—S1−62.56 (10)O6—S2—C5—C634.94 (14)
O8—S1—C7—C8151.35 (11)O5—S2—C5—C6164.17 (12)
O7—S1—C7—C817.44 (13)N3—S2—C5—C6−78.65 (13)
N3—S1—C7—C8−95.14 (12)C11—C10—C9—C80.0 (2)
O8—S1—C7—C12−30.00 (13)N2—C10—C9—C8179.28 (11)
O7—S1—C7—C12−163.91 (11)C7—C8—C9—C10−0.02 (19)
N3—S1—C7—C1283.51 (12)C5—C4—C3—C2−1.3 (2)
C12—C7—C8—C9−0.2 (2)C9—C10—N2—O4−14.29 (18)
S1—C7—C8—C9178.44 (10)C11—C10—N2—O4164.99 (13)
O1—N1—C6—C1−152.05 (15)C9—C10—N2—O3166.50 (14)
O2—N1—C6—C126.4 (2)C11—C10—N2—O3−14.22 (19)
O1—N1—C6—C525.4 (2)C4—C3—C2—C13.1 (2)
O2—N1—C6—C5−156.21 (15)C5—C6—C1—C2−1.3 (2)
C10—C11—C12—C7−0.3 (2)N1—C6—C1—C2176.21 (13)
C8—C7—C12—C110.3 (2)C3—C2—C1—C6−1.8 (2)
S1—C7—C12—C11−178.29 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8B···O70.952.532.902 (2)104.
C4—H4A···O50.952.382.803 (2)106.
C13—H13A···O70.982.542.978 (2)107.
C13—H13C···O10.982.342.972 (2)122.
C1—H1A···O6i0.952.513.369 (2)150.

Symmetry codes: (i) x, −y−1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2239).

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.
  • Curtis, V. A. & Pavkovic, S. F. (1983). Acta Cryst. C39, 1077–1078.
  • Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent. US 4 670 046.
  • Rigaku (2004). RAPID-AUTO Rigaku Corporation, Takyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem 265, 9–14.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography