2-Chloro-N-(2-chloro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810012808

. 2010 Apr 10;66(Pt 5):o1040. doi: 10.1107/S1600536810012808

2-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide

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

PMCID: PMC2979121 PMID: 21579101

Abstract

In the structure of the title compound, C₁₃H₉Cl₂NO₃S, the N—H bond is anti to the C=O bond and the dihedral angle between the two aromatic rings is 76.9 (1)°. In the crystal structure, molecules are linked by N—H⋯O(S) hydrogen bonds to form inversion dimers.

Related literature

For background literature and similar structures, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S
M _r = 330.17
Monoclinic,
a = 6.5943 (6) Å
b = 10.9167 (9) Å
c = 20.167 (2) Å
β = 95.83 (1)°
V = 1444.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 299 K
0.36 × 0.20 × 0.06 mm

Data collection

Oxford Xcalibur with a Sapphire CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.813, T _max = 0.965
5854 measured reflections
2942 independent reflections
1919 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.098
S = 1.01
2942 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.31 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/S1600536810012808/bt5238sup1.cif

e-66-o1040-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012808/bt5238Isup2.hkl

e-66-o1040-Isup2.hkl^{(144.4KB, 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⋯O2ⁱ	0.85 (1)	2.06 (1)	2.913 (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

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, 2010a,b), the structure of N-(2-chlorobenzoyl)2-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-(2-chlorobenzoyl)benzenesulfonamide (III)(Gowda et al., 2010a) and N-(benzoyl)2-chlorobenzenesulfonamide (IV)(Gowda et al., 2010b).

Further, the conformation of the C═O bond in the C—SO₂—NH—C(O) segment of (I) is syn to the ortho-Cl in the benzoyl ring, similar to that observed in (III).

The molecules are twisted at the S atom with the torsional angle of 66.5 (2)°, compared to those of -66.9 (3)° in (II), -59.0 (2)° (molecule 1) and -67.3 (2)° (molecule 2) in (III), and 66.7 (2)° in (IV).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 86.9 (1)°, compared to the values of 86.5(0.1) in (II), 87.3 (1)° (molecule 1) and 73.3 (1)° (molecule 2) in (III), and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 76.9 (1)°, compared to the values of 80.3(0.1) in (II), 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (III) and 73.3 (1)° in (IV).

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 2-chlorobenzoic 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.