2-Chloro-N-(4-methyl­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810018908

. 2010 May 26;66(Pt 6):o1466. doi: 10.1107/S1600536810018908

2-Chloro-N-(4-methylbenzoyl)benzenesulfonamide

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

PMCID: PMC2979447 PMID: 21579534

Abstract

In the title compound, C₁₄H₁₂ClNO₃S, 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 sulfonyl benzene ring and the —SO₂—NH—C—O segment is 89.4 (1)° and that between the sulfonyl and benzoyl benzene rings is 89.1 (2)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2010a ▶,b ▶); Suchetan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M _r = 309.76
Monoclinic,
a = 8.0554 (8) Å
b = 23.209 (2) Å
c = 8.1199 (9) Å
β = 103.52 (1)°
V = 1476.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 299 K
0.40 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.855, T _max = 0.906
6106 measured reflections
3012 independent reflections
2396 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.153
S = 1.07
3012 reflections
184 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.54 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/S1600536810018908/bq2212sup1.cif

e-66-o1466-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018908/bq2212Isup2.hkl

e-66-o1466-Isup2.hkl^{(147.8KB, 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⋯O2ⁱ	0.84 (2)	2.14 (2)	2.970 (4)	169 (4)

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Symmetry code: (i) Inline graphic .

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 a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2010a,b; Suchetan et al., 2010a,b), the structure of 2-chloro-N-(4-methylbenzoyl)benzenesulfonamide (I) has been determined (Fig.1). The conformations of the N—C bonds in the C—SO₂—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond, similar to that observed in 2-methyl-N-(4-methylbenzoyl)-benzenesulfonamide (II) (Gowda et al., 2010a), 2-chloro-N-(3-methylbenzoyl)-benzenesulfonamide (III) (Suchetan et al., 2010b), 2-chloro-N-(2-methylbenzoyl)- benzenesulfonamide (IV) (Suchetan et al., 2010a) and 2-chloro-N-(benzoyl)-benzenesulfonamide (V) (Gowda et al., 2010b).

The molecules are twisted at the S atom with the torsional angle of 60.4 (3)°, compared to those of -53.1 (2)° and 61.2 (2)°, in the two molecules of (II), -66.5 (2)° in (III), -64.0 (2)° in (IV) and 66.7 (2)° in (V). The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 89.4 (1)°, compared to the values of 86.0 (1)° and 87.9 (1)° in the 2 molecules of (II), 88.4 (1)° in (III), 84.8 (1)° in (IV) and 87.3 (1)° in (V).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene ring is 89.1 (2)°, compared to the values of 88.1 (1)° (molecule 1) and 83.5 (1)° (molecule 2) of (II), 74.7 (1)° in (III), 78.7 (1)° in (IV) and 73.3 (1)° in (V).

The packing of molecules linked by 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 4-methylbenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid, 2-chloro-N-(4-methylbenzoyl)benzenesulfonamide 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 compound was recrystallized to the constant melting point.

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