N-Benzo­ylbenzene­sulfonamide

B Thimme Gowda; Sabine Foro; P A Suchetan; Hartmut Fuess

doi:10.1107/S1600536809037222

. 2009 Sep 26;65(Pt 10):o2516. doi: 10.1107/S1600536809037222

N-Benzoylbenzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, P A Suchetan ^a, Hartmut Fuess ^b

PMCID: PMC2970249 PMID: 21577963

Abstract

In the crystal structure of the title compound, C₁₃H₁₁NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O)—C segment is anti to the C=O bond. The molecule is twisted at theN atom with a dihedral angle of 86.5(1)° between the sulfonyl benzene ring and the —SO₂—NH—C=O segment. Furthermore, the dihedral angle between the two benzene rings is 80.3(1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a ▶,b ▶; 2009 ▶).

Experimental

Crystal data

C₁₃H₁₁NO₃S
M _r = 261.29
Triclinic,
a = 5.8396 (7) Å
b = 10.178 (1) Å
c = 10.405 (1) Å
α = 90.187 (8)°
β = 99.074 (9)°
γ = 99.617 (9)°
V = 601.83 (11) Å³
Z = 2
Cu Kα radiation
μ = 2.40 mm⁻¹
T = 299 K
0.50 × 0.33 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan North et al., 1968 ▶ T _min = 0.380, T _max = 0.889
2354 measured reflections
2125 independent reflections
1962 reflections with I > 2σ(I)
R _int = 0.011
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.171
S = 1.18
2125 reflections
167 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809037222/tk2540sup1.cif

e-65-o2516-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037222/tk2540Isup2.hkl

e-65-o2516-Isup2.hkl^{(104.5KB, 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
N1—H1N⋯O1ⁱ	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent anti-tumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. As part of a study of the effect of ring and the side chain substituents on the solid-state structures of N-aromatic sulfonamides (Gowda et al., 2008a,b; 2009), in the present work the structure of N-(benzoyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in the structure is anti to the C═O bond in the side-chain, similar to that observed in the acid anilides. The conformation of the N—C bond in the C—SO₂—NH—C(O) segment of the structure has "gauche" torsions with respect to the SO bonds (Fig. 1). The molecule is twisted at the C(O) atom with the C—SO₂—NH—C(O) torsion angle being -66.9 (3)°. The packing of molecules via N—H···O(S) hydrogen bonds (Table 1) into supramolecular dimers is shown in Fig. 2.

Experimental

Compound (I) was prepared by refluxing a mixture of benzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice-cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. Compound (I) was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point. The compound was characterized by its characteristic aromatic C—H stretching (3061.1 cm^-1), carbonyl C═O (1696.7 cm^-1), N—H stretching (3280.1 cm^-1), symmetric (1176.3 cm^-1), and asymmetric SO₂ (1335.1 cm^-1) infrared absorption frequencies.

Long colorless plates of (I) were obtained from a slow evaporation of its toluene solution at room temperature.