N-(3-Chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809041051

. 2009 Oct 17;65(Pt 11):o2750. doi: 10.1107/S1600536809041051

N-(3-Chlorobenzoyl)benzenesulfonamide

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

PMCID: PMC2971321 PMID: 21578344

Abstract

In the crystal structure of the title compound, C₁₃H₁₀ClNO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the two benzene rings is 87.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2008 ▶); Gowda, Foro, Nirmala et al. (2009 ▶); Gowda, Foro, Suchetan et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₁₀ClNO₃S
M _r = 295.73
Monoclinic,
a = 21.309 (2) Å
b = 6.0953 (7) Å
c = 20.367 (2) Å
β = 92.48 (1)°
V = 2642.9 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 299 K
0.42 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.834, T _max = 0.900
5328 measured reflections
2714 independent reflections
1968 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.133
S = 0.92
2714 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536809041051/pk2198sup1.cif

e-65-o2750-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041051/pk2198Isup2.hkl

e-65-o2750-Isup2.hkl^{(133.4KB, 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	0.84 (2)	2.12 (2)	2.946 (2)	171 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor 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 crystal structures of N-aromatic sulfonamides (Gowda et al., 2008; Gowda, Foro, Nirmala et al., 2009; Gowda, Foro, Suchetan et al., 2009), in the present work, the structure of N-(3-chlorobenzoyl)benzenesulfonamide (I) has been determined (Fig.1). The conformation of the of the N—H bond in the C—SO₂—NH—C(O) segment of the structure is anti to the C=O bond, similar to that observed in N-(benzoyl)benzenesulfonamide (II) (Gowda, Foro, Suchetan et al., 2009). Further, the C=O bond in the segment is anti to the meta-Cl in the benzoyl ring, while 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. The molecule is twisted at the N atom with a dihedral angle of 89.9 (1)° between the sulfonyl benzene ring and the C—SO₂—NH—C—O segment, compared to the value of 86.5 (1)° in (II). The dihedral angle between the two benzene rings is 87.5 (1)° in (I) and 80.3 (1)° in (II). The packing of molecules linked by pairs of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid, benzene sulfonamide and phosphorous oxychloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.

Prism-like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its toluene solution at room temperature.