N-(4-Chloro­benzo­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809055585

. 2010 Jan 9;66(Pt 2):o327. doi: 10.1107/S1600536809055585

N-(4-Chlorobenzoyl)-4-methylbenzenesulfonamide

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

PMCID: PMC2979700 PMID: 21579757

Abstract

The asymmetric unit of the title compound, C₁₄H₁₂ClNO₃S, contains two independent molecules. The dihedral angles between the two aromatic rings in each molecule are 81.0 (1) and 76.3 (1)°. In the crystal, molecules are linked 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

C₁₄H₁₂ClNO₃S
M _r = 309.76
Monoclinic,
a = 25.675 (3) Å
b = 12.0508 (8) Å
c = 22.191 (3) Å
β = 122.16 (1)°
V = 5812.5 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 299 K
0.50 × 0.48 × 0.44 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.821, T _max = 0.840
12864 measured reflections
5931 independent reflections
3733 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.130
S = 1.07
5931 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 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/S1600536809055585/bt5156sup1.cif

e-66-0o327-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055585/bt5156Isup2.hkl

e-66-0o327-Isup2.hkl^{(290.4KB, 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⋯O5ⁱ	0.84 (1)	2.35 (1)	3.133 (3)	156 (2)
N2—H2N⋯O2ⁱⁱ	0.87 (1)	2.03 (1)	2.890 (3)	170 (2)

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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 the crystal structures of N-aromatic sulfonamides (Gowda et al., 2009a,b; Suchetan et al., 2009), in the present work, the structure of N-(4-chlorobenzoyl)4-methylbenzenesulfonamide (I) has been determined (Fig.1). The conformations of the N—H bonds in the C—SO₂—NH—C(O) segments of the structure are anti to the C=O bonds, similar to that observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009a) and N-(4-chlorobenzoyl) benzenesulfonamide (III)(Suchetan et al., 2009).

The molecules are twisted at the S atom with the torsional angles of 67.1 (2)° and 67.7 (2)°, in the two molecules. The dihedral angles between the sulfonyl benzene ring and the —SO₂—NH—C—O segment are 83.6 (1)° and 81.0 (1)°, compared to the values of 86.5(0.1) in (II) and 75.7 (1)° in (III). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings in (I) are 81.0 (1)° and 76.3 (1)°, compared to the values of 80.3(0.1) in (II) and 68.6 (1)° in (III).

The dihedral angle between the sulfonyl benzene rings of the two molecules in the asymmetric unit is 45.8 (1)°. The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

N-(4-Chlorobenzoyl)4-methylbenzenesulfonamide was prepared by heating a mixture of 4-methylbenzenesulfonamide and 4-chlorobenzoyl chloride at 60° C for one hour. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in sodium hydrogen carbonate solution. The compound was precipitated by acidifying the filtered solution with dil. HCl. It was filtered and dried. The purity of the compound was checked by recording its melting point (168–170° C). Single crystals were obtained from slow evaporation of a solution of the compound in toluene. Prism like colourless single crystals of the title compound were obtained from a slow evaporation of its toluene solution at room temperature and the X-ray diffraction studies were also carried out at room temperature.