N-(2-Chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809055482

. 2010 Jan 9;66(Pt 2):o326. doi: 10.1107/S1600536809055482

N-(2-Chlorobenzoyl)benzenesulfonamide

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

PMCID: PMC2979754 PMID: 21579756

Abstract

The asymmetric unit of the title compound, C₁₃H₁₀ClNO₃S, contains two independent molecules, the chlorophenyl ring of one of them being disordered over two orientations with occupancies of 0.836 (2) and 0.164 (2). In one of the independent molecules, the sulfonyl-bound phenyl ring and the chlorophenyl ring form dihedral angles of 87.3 (1) and 46.8 (1)°, respectively, with the –S–NH–C=O segment, while in the other molecule the corresponding angles are 76.0 (1) and 39.6 (1)°. In the crystal, molecules are linked into tetrameric units by N—H⋯O hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2009a ▶,b ▶); Suchetan et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₁₀ClNO₃S
M _r = 295.73
Triclinic,
a = 7.3390 (5) Å
b = 10.828 (1) Å
c = 17.685 (1) Å
α = 93.088 (6)°
β = 96.863 (7)°
γ = 103.057 (8)°
V = 1354.46 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 299 K
0.50 × 0.44 × 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 = 0.811, T _max = 0.902
9641 measured reflections
5521 independent reflections
4327 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.113
S = 1.03
5521 reflections
359 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.34 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/S1600536809055482/ci5004sup1.cif

e-66-0o326-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055482/ci5004Isup2.hkl

e-66-0o326-Isup2.hkl^{(270.3KB, 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
N1—H1N⋯O1ⁱ	0.84 (2)	2.09 (2)	2.922 (2)	168 (2)
N2—H2N⋯O3ⁱⁱ	0.82 (2)	2.06 (2)	2.883 (2)	179 (3)

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

Acknowledgments

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of a study of the effect of ring and the side chain substituents on crystal structures of N-aromatic sulfonamides (Gowda et al., 2009a,b; Suchetan et al., 2009), in the present work, the structure of N-(2-chlorobenzoyl)benzenesulfonamide (I) has been determined (Fig.1).

The asymmetric unit of the title compound contains two independent molecules, A (with S1) and B (with S2). The conformation 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 et al., 2009a), N-(3-chlorobenzoyl)benzenesulfonamide (III) (Gowda et al., 2009b) and N-(4-chlorobenzoyl)benzenesulfonamide (IV) (Suchetan et al., 2009).

Both independent molecules are twisted at their S atoms; the dihedral angle between the sulfonyl-bound phenyl ring and the S—N(H)—C═O segment is 87.3 (1)° in molecule A and 76.0 (1)° in molecule B, compared to the values of 86.5(0.1) in (II), 89.9 (1)° in (III) and 75.7 (1)° in (IV). Furthermore, the dihedral angle between the chlorophenyl ring and the S—NH—C═O segment is 46.8 (1)° in molecule A and 39.6 (1)° in molecule B.

The dihedral angles between the two phenyl rings in the two molecules of (I) are 69.8 (1)° (molecule A) and 89.8 (1)° (molecule B), compared to the values of 80.3(0.1) in (II), 87.5 (1)° in (III) and 68.6 (1)° in (IV).

The packing of molecules linked by of N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of 2-chlorobenzoic acid, benzenesulfonamide and phosphorous oxy chloride for 3 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. It was filtered, dried and recrystallized. Rod like colourless single crystals of the title compound were obtained by slow evaporation of its toluene solution at room temperature.