2-Chloro-N-(3-methyl­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810016235

. 2010 May 8;66(Pt 6):o1292. doi: 10.1107/S1600536810016235

2-Chloro-N-(3-methylbenzoyl)benzenesulfonamide

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

PMCID: PMC2979524 PMID: 21579389

Abstract

In the title compound, C₁₄H₁₂ClNO₃S, the N—H bond is in an antiperiplanar conformation to the C=O bond. The dihedral angle between the two aromatic rings is 74.7 (1)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl sulfonamides and for related structures, see: Gowda et al. (2009 ▶, 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M _r = 309.76
Orthorhombic,
a = 12.4487 (8) Å
b = 13.4619 (8) Å
c = 17.455 (1) Å
V = 2925.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 299 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.887, T _max = 0.923
7216 measured reflections
2955 independent reflections
2422 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.095
S = 1.04
2955 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 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/S1600536810016235/bt5261sup1.cif

e-66-o1292-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016235/bt5261Isup2.hkl

e-66-o1292-Isup2.hkl^{(145.1KB, 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	0.82 (2)	2.16 (2)	2.974 (2)	176 (2)

Open in a new tab

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

As a part of studying the effect of ring and the side chain substitutions on the crystal structures of N-aryl sulfonamides (Gowda et al., 2009, 2010; Suchetan et al., 2010)), in the present work, the structure of 2-chloro-N-(3-methylbenzoyl)benzenesulfonamide, (I), has been determined. In the C—SO₂—NH—C(O) segment, the N—H bond is anti to the C=O bond (Fig.1), similar to those observed in 2-chloro-N-(2-methylbenzoyl)benzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010).

Further, the conformation of the C=O bond in the C—SO₂—NH—C(O) segment of (I) is anti to the meta-methyl group in the benzoyl ring, contrary to the syn conformation observed between the ortho-methyl group and the C=O bond in (II).

The molecules are twisted at the S atom with the torsional angle of -66.5 (2)°, compared to those of -64.0 (2)° in (II), -66.9 (3)° in (III), and 66.7 (2)° in (IV).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.4 (1)°, compared to the values of 84.8 (1)° in (II), 86.5 (1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 74.7 (1)°, compared to the values of 78.7 (1)° in (II), of 80.3 (1) in (III) and 73.3 (1)° in (IV).

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

Experimental

The title compound was prepared by refluxing a mixture of 3-methylbenzoic acid, 2-chlorobenzenesulfonamide 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.

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