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

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

doi:10.1107/S1600536810019057

. 2010 May 26;66(Pt 6):o1467. doi: 10.1107/S1600536810019057

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

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

PMCID: PMC2979439 PMID: 21579535

Abstract

In the structure of 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 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2010 ▶); Suchetan et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₃H₉Cl₂NO₃S
M _r = 330.17
Triclinic,
a = 6.3882 (9) Å
b = 10.311 (1) Å
c = 11.171 (1) Å
α = 79.01 (1)°
β = 74.47 (1)°
γ = 84.76 (1)°
V = 695.32 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 299 K
0.24 × 0.20 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.865, T _max = 0.918
4417 measured reflections
2825 independent reflections
2378 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.107
S = 1.06
2825 reflections
184 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.52 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/S1600536810019057/xu2765sup1.cif

e-66-o1467-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019057/xu2765Isup2.hkl

e-66-o1467-Isup2.hkl^{(138.6KB, 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	0.81 (2)	2.13 (2)	2.914 (2)	164 (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., 2010; Suchetan et al., 2010a,b,c), the structure of N-(2-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-(2-chlorobenzoyl)-benzenesulfonamide (II) (Gowda et al., 2010), N-(benzoyl)-4-chlorobenzenesulfonamide (III) (Suchetan et al., 2010a), N-(2-chlorobenzoyl)-2-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010b) and N-(4-chlorobenzoyl)-4- chlorobenzenesulfonamide (V) (Suchetan et al., 2010c).

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 (II) and (IV).

The molecules are twisted at the S atom with the torsional angle of 65.7 (2)°, compared to those of -59.0 (2)° (molecule 1) and -67.3 (2)° (molecule 2) in (II), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (III), 66.5 (2)° in (IV) and 67.5 (3)° in (V).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 88.5 (1)°, compared to the values of 87.3 (1)° (molecule 1) and 73.3 (1)° (molecule 2) in (II), 72.0 (1)° & 77.3 (1)° in the two molecules of (III), 86.9 (1)° in (IV) and 79.0 (1)° in (V).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°, compared to the values of 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (II), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (III), 76.9 (1)° in (IV) and 85.6 (1)° in (V)

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, 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.