2-Amino-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

Zu-Wei Song

doi:10.1107/S1600536808007447

. 2008 Mar 29;64(Pt 4):o744. doi: 10.1107/S1600536808007447

2-Amino-N-(4-methylphenylsulfonyl)-N-phenylbenzenesulfonamide

Zu-Wei Song ^a,^*

PMCID: PMC2960949 PMID: 21202134

Abstract

In the title molecule, C₁₉H₁₈N₂O₄S₂, the phenyl ring makes dihedral angles of 33.99 (2) and 43.70 (3)° with the two methyl-substituted benzene rings. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 ▶). For details of the biological activities of sulfonamide-containing compounds, see: Kamoshita et al. (1987 ▶). For related literature, see: Allen et al. (1987 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₁₈N₂O₄S₂
M _r = 402.47
Monoclinic,
a = 14.6245 (3) Å
b = 10.0454 (2) Å
c = 13.4735 (4) Å
β = 107.478 (2)°
V = 1887.99 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 (2) K
0.52 × 0.32 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi 1995 ▶) T _min = 0.855, T _max = 0.926
17437 measured reflections
4312 independent reflections
3531 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.121
S = 1.07
4312 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 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/S1600536808007447/cv2388sup1.cif

e-64-0o744-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007447/cv2388Isup2.hkl

e-64-0o744-Isup2.hkl^{(211.3KB, 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
N2—H2B⋯O3ⁱ	0.86	2.20	3.062 (2)	176
C19—H19A⋯O1ⁱⁱ	0.96	2.57	3.517 (3)	169
C19—H19C⋯O4ⁱⁱⁱ	0.96	2.58	3.538 (3)	174
N2—H2C⋯O2	0.86	2.23	2.893 (2)	133

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

supplementary crystallographic information

Comment

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as 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 normal (Allen et al., 1987) and in a good agreement with those reported previously (Henschel et al., 1996). The phenyl ring (C7—C12) makes the dihedral angles of 33.99 (2) and 43.70 (3)°, respectively, with two benzene rings (C1—C6/N1 and C13—C19). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

A solution of methylsulfonyl chloride (1 mmol) was dissolved in anhydrous CH₂Cl₂ (10 ml), and dropwise added over a period of 10 min to a solution of 2-amino-N-methyl-benzenesulfonamide (1 mmol) and DMAP₂ (3 mmol) in CH₂Cl₂ (10 ml) at 273 K. The mixture was stirred for 4 h at room temperature. The organic phase was washed with 2 N HCl twice, and dried over anhydrous Na₂SO₄. The solvent was removed and the residue was purified by flash chromatography (1:1 cyclohexane:dichloromethane) to give (I) as a white solid (294 mg, 73%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.