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

Haiyan Lu

doi:10.1107/S1600536808027499

. 2008 Sep 6;64(Pt 10):o1885. doi: 10.1107/S1600536808027499

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

Haiyan Lu ^a,^*

PMCID: PMC2959441 PMID: 21201097

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 ▶); Curtis & Pavkovic (1983 ▶). For details of the biological activities of sulfonamide compounds, see: Kamoshita et al. (1987 ▶). For details of the application of sulfonimade catalysts, see: Zhang et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₁₁N₃O₈S₂
M _r = 401.37
Monoclinic,
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 ▶) 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
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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

Supplementary Material

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

e-64-o1885-sup1.cif^{(19.3KB, cif)}

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

e-64-o1885-Isup2.hkl^{(180.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O7	0.95	2.53	2.902 (2)	104
C4—H4A⋯O5	0.95	2.38	2.803 (2)	106
C13—H13A⋯O7	0.98	2.54	2.978 (2)	107
C13—H13C⋯O1	0.98	2.34	2.972 (2)	122
C1—H1A⋯O6ⁱ	0.95	2.51	3.369 (2)	150

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Symmetry code: (i) Inline graphic .

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.