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

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

doi:10.1107/S1600536810016909

. 2010 May 15;66(Pt 6):o1343. doi: 10.1107/S1600536810016909

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

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

PMCID: PMC2979644 PMID: 21579432

Abstract

The asymmetric unit of the title compound, C₁₃H₉Cl₂NO₃S, contains two independent molecules. The conformation of the C=O bond is anti to the meta-Cl group in the chlorobenzoyl group of one of the molecules and syn in the other. The dihedral angles between the sulfonyl and benzoyl benzene rings are 77.8 (1) and 83.5 (1)°. In the crystal structure, two pairs of independent molecules are linked into a tetramer by N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S
M _r = 330.17
Triclinic,
a = 7.4399 (6) Å
b = 11.679 (1) Å
c = 17.138 (2) Å
α = 75.346 (7)°
β = 83.188 (8)°
γ = 77.732 (7)°
V = 1404.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 299 K
0.20 × 0.14 × 0.08 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 = 0.952
9768 measured reflections
5694 independent reflections
4267 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.154
S = 1.04
5694 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.50 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/S1600536810016909/ci5091sup1.cif

e-66-o1343-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016909/ci5091Isup2.hkl

e-66-o1343-Isup2.hkl^{(278.7KB, 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⋯O6	0.84 (2)	2.02 (2)	2.836 (4)	162 (4)
N2—H2N⋯O5ⁱ	0.85 (2)	2.10 (2)	2.937 (4)	173 (4)

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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 substitutions on the crystal structures of N-aryl sulfonamides (Gowda et al., 2009, 2010; Suchetan et al., 2010a,b), the structure of 2-chloro-N-(3-chlorobenzoyl)-benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains two independent molecules. In the C—SO₂—NH—C(O) segments, the N—H bonds are anti to the C═O bonds (Fig.1), similar to those observed in 2-chloro-N- (3-methylbenzoyl)-benzenesulfonamide (II) (Suchetan et al., 2010b), 2-methyl-N-(3-methylbenzoyl)-benzenesulfonamide (III) (Gowda et al., 2010), 2-chloro-N-(2-chlorobenzoyl)- benzenesulfonamide (IV)(Suchetan et al., 2010a), N-(benzoyl)-benzenesulfonamide (V) (Gowda et al., 2009).

The conformation of the C═O bond is anti to the meta-Cl group in the benzoyl ring of one of the molecules and syn in the other, compared to the anti conformation observed between C═O bond and meta- methyl group in the benzoyl ring of (II).

The chlorobenzoyl and sulfonyl-bound chlorophenyl units in the two molecules of (I) are twisted with respect to the S—N bond, with torsional angles of -62.6 (3)° [C7—N1—S1—C1] and -62.6 (3)° [C20—N2—S2—C14], compared to those of -66.5 (2)° in (II), -66.2 (3)° in (III), -66.5 (2)° in (IV) and -66.9 (3)° in (V). The dihedral angles between the sulfonyl and the benzoyl- bound benzene rings are 77.8 (1)° (molecule 1) and 83.5 (1)° (molecule 2), compared to the values of 74.7 (1)° in (II), 74.8 (1)° in (III), 76.9 (1) in (IV) and 80.3 (1)° in (V).

Experimental

The title compound was prepared by refluxing a mixture of 3-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. Rod 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.