N-(2-Amino­phenyl­sulfonyl)-N-(2-nitro­phenyl­sulfonyl)methylamine

Xu-Yun Li; Zu-Wei Song

doi:10.1107/S1600536808028092

. 2008 Sep 13;64(Pt 10):o1906. doi: 10.1107/S1600536808028092

N-(2-Aminophenylsulfonyl)-N-(2-nitrophenylsulfonyl)methylamine

Xu-Yun Li ^a, Zu-Wei Song ^a,^*

PMCID: PMC2959438 PMID: 21201116

Abstract

In the title molecule, C₁₃H₁₃N₃O₆S₂, the two benzene rings form a dihedral angle of 28.59 (7)°. The crystal sructure exhibits weak intermolecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds and π–π interactions [centroid-to-centroid distance = 3.899 (3) Å].

Related literature

For applications of sulfonimide-containing compounds, see: Kamoshita et al. (1987 ▶); Zhang et al. (2007 ▶). For the crystal structure of a related compound, see: Henschel et al. (1996 ▶).

Experimental

Crystal data

C₁₃H₁₃N₃O₆S₂
M _r = 371.38
Orthorhombic,
a = 13.844 (3) Å
b = 12.942 (2) Å
c = 16.645 (3) Å
V = 2982.2 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 153 (2) K
0.60 × 0.56 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.733, T _max = 0.969
34829 measured reflections
2630 independent reflections
2428 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.087
S = 1.08
2630 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 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/S1600536808028092/cv2436sup1.cif

e-64-o1906-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028092/cv2436Isup2.hkl

e-64-o1906-Isup2.hkl^{(129.3KB, 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
N3—H3C⋯O1ⁱⁱ	0.88	2.52	3.366 (2)	160
C12—H12A⋯O2ⁱⁱ	0.95	2.59	3.508 (3)	162
C9—H9A⋯N3ⁱⁱⁱ	0.95	2.59	3.372 (3)	140

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Symmetry codes: (ii) Inline graphic ; (iii) .

supplementary crystallographic information

Comment

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987) or catalysts (Zhang et al., 2007). Herein we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are in a good agreement with those reported previously for related compounds (Henschel et al., 1996). Two benzene rings (C1–C6 and C8–C13) form a dihedral angle of 28.59 (7)°.

The crystal packing exhibits π–π interactions (Table 1) and weak intermolecular N—H···O, C—H···N and C—H···O hydrogen bonds (Table 2).

Experimental

A solution of 2-aminobenzene-1-sulfonyl chloride (10 mmol) 1.92 g dissolved in anhydrous CH₂Cl₂ (10 ml), and dropwise added over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (10 mmol) 2.16g and EtN(i-Pr)₂ (3 mmol) in CH₂Cl₂ (10 ml) at 273 K. The mixture was stirred at r.t. 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 (3:1 Cyclohexane:Dichloromethane) to give 1 as a white solid (3.52 mg, 95 %). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and Dichloromethane at room temperature.