2-Chloro-N-(4-chloro­benzo­yl)benzene­sulfonamide toluene hemisolvate

P A Suchetan; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536810052281

. 2010 Dec 18;67(Pt 1):o146. doi: 10.1107/S1600536810052281

2-Chloro-N-(4-chlorobenzoyl)benzenesulfonamide toluene hemisolvate

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

PMCID: PMC3050374 PMID: 21522654

Abstract

The unit cell of the title compound, C₁₃H₉Cl₂NO₃S·0.5C₇H₈, contains two molecules of 2-chloro-N-(4-chlorobenzoyl)benzenesulfonamide and one toluene molecule, which is disordered about a centre of inversion. The dihedral angle between the two aromatic rings is 85.7 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming centrosymmetric dimers.

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 similar structures, see: Gowda et al. (2010a ▶,b ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S·0.5C₇H₈
M _r = 376.24
Triclinic,
a = 7.5992 (9) Å
b = 10.876 (1) Å
c = 11.346 (1) Å
α = 73.868 (8)°
β = 75.927 (9)°
γ = 70.994 (8)°
V = 839.58 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 299 K
0.44 × 0.44 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.802, T _max = 0.834
5654 measured reflections
3405 independent reflections
2941 reflections with I > 2σ(I)
R _int = 0.009

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.099
S = 1.06
3405 reflections
229 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.43 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/S1600536810052281/bt5432sup1.cif

e-67-0o146-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052281/bt5432Isup2.hkl

e-67-0o146-Isup2.hkl^{(167KB, 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	0.82 (2)	2.13 (2)	2.951 (2)	176 (2)

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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

In the present work, 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., 2010a,b; Suchetan et al., 2010), the structure of 2-chloro-N-(4-chlorobenzoyl)benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains also half a molecule of toluene which is disordered about a centre of inversion. The conformation of the N—C bond in the C—SO₂—NH—C(O) segment has gauche torsions with respect to the SO bonds. In these segments, the N—H bond is anti to the C=O bond (Fig. 1), similar to those observed in 2-chloro-N-(2-chlorobenzoyl)-benzenesulfonamide (II) (Suchetan et al., 2010), 2-chloro-N-(3-chlorobenzoyl)benzenesulfonamide (III) (Gowda et al., 2010b)), 2-methyl-N- (4-methylbenzoyl)benzenesulfonamide (IV) (Gowda et al., 2010a).

The molecule in (I) is twisted at the S atom with the C—SO₂—NH—C(O) torsional angle of -62.7 (2)°, compared to those of -66.5 (2)° in (II), -62.6 (3)° and -62.6 (2)° in the two molecules of (III), and -53.1 (2)° and 61.2 (2)° in the two independent molecules of (IV).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.5 (1)°, compared to the values of 86.9 (1) in (II), 89.9 (1)° and 86.4 (1)° in the two molecules of (III), and 86.0 (1)° (molecule 1) and 87.9 (1)° (molecule 2) in (IV).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 85.7 (1)°, compared to the values of 76.9 (1) in (II), 77.8 (1)° (molecule 1) and 83.5 (1)° (molecule 2) in (III), and 88.1 (1)° and 83.5 (1)° in the two independent molecules of (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 4-chlorobenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxychloride 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 a slow evaporation of its toluene solution at room temperature.