4-Chloro-N-(4-chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S160053681001559X

. 2010 May 8;66(Pt 6):o1253. doi: 10.1107/S160053681001559X

4-Chloro-N-(4-chlorobenzoyl)benzenesulfonamide

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

PMCID: PMC2979647 PMID: 21579357

Abstract

In the title compound, C₁₃H₉Cl₂NO₃S, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The molecule is twisted at the S atom with a torsion angle of 67.5 (3)°. The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 79.0 (1)° and that between the sulfonyl and benzoyl benzene rings is 85.6 (1)°. In the crystal, molecules are linked by N—H⋯O(S) hydrogen bonds with graph-set descriptor C(4) along the [010] direction.

Related literature

For background literature and related structures, see: Gowda et al. (2009 ▶); Suchetan et al. (2009 ▶, 2010a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S
M _r = 330.17
Orthorhombic,
a = 13.6405 (9) Å
b = 9.6495 (8) Å
c = 21.116 (2) Å
V = 2779.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 299 K
0.34 × 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 = 0.816, T _max = 0.886
10651 measured reflections
2550 independent reflections
1946 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.102
S = 1.07
2550 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.44 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/S160053681001559X/bx2279sup1.cif

e-66-o1253-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001559X/bx2279Isup2.hkl

e-66-o1253-Isup2.hkl^{(125.4KB, 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⋯O3ⁱ	0.85 (1)	2.23 (1)	3.074 (3)	172 (3)

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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

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., 2009; Suchetan et al.,2009, 2010a,b), the structure of N-(4-chlorobenzoyl)-4-chlorobenzenesulfonamide (I) has been determined. The conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(4-chlorobenzoyl)-benzenesulfonamide (III)(Suchetan et al., 2009), N-(benzoyl)-4-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010a) and N-(2-chlorobenzoyl)- 2-chlorobenzenesulfonamide (V)(Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the torsional angles of 67.5 (3)°, compared to the values of -66.9 (3)° in (II), 69.4 (2)° in (III), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (IV) and 66.5 (2)° in (V).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 85.6 (1)°, compared to the vlues of 80.3 (1) in (II), 68.6 (1)° in (III), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (IV) and 76.9 (1)° in (V).

The molecules are linked by of N—H···O(S) hydrogen bonds with graph-set descriptor C(4) along [010] direction, ( Bernstein et al., 1995) (Table 1), Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of 4-chlorobenzoic acid, 4-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.