N-(2,4-Dichloro­phen­yl)benzene­sulfonamide

B Thimme Gowda; Sabine Foro; P G Nirmala; Hartmut Fuess

doi:10.1107/S160053680905452X

. 2009 Dec 24;66(Pt 1):o229. doi: 10.1107/S160053680905452X

N-(2,4-Dichlorophenyl)benzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, P G Nirmala ^a, Hartmut Fuess ^b

PMCID: PMC2980121 PMID: 21580110

Abstract

The title compound, C₁₂H₉Cl₂NO₂S, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the two aromatic rings are 70.8 (1) and 74.8 (1)° for the two molecules. The crystal structure features dimers made up of one each of the two asymmetric molecules linked by pairs of N—H⋯O hydrogen bonds. An intramolecular N—H⋯Cl hydrogen bond is also observed in both molecules.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008 ▶; 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₉Cl₂NO₂S
M _r = 302.16
Monoclinic,
a = 8.2428 (6) Å
b = 19.473 (1) Å
c = 16.873 (1) Å
β = 103.317 (7)°
V = 2635.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 299 K
0.50 × 0.24 × 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 = 0.740, T _max = 0.915
17396 measured reflections
4807 independent reflections
3444 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.106
S = 1.08
4807 reflections
331 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 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/S160053680905452X/bt5148sup1.cif

e-66-0o229-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905452X/bt5148Isup2.hkl

e-66-0o229-Isup2.hkl^{(235.5KB, 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⋯O4	0.85 (1)	2.19 (1)	3.015 (3)	165 (3)
N1—H1N⋯Cl1	0.85 (1)	2.60 (3)	2.998 (3)	110 (2)
N2—H2N⋯O2	0.85 (1)	2.38 (2)	3.192 (4)	160 (3)
N2—H2N⋯Cl3	0.85 (1)	2.55 (3)	2.996 (3)	113 (3)

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supplementary crystallographic information

Comment

In the present work, as part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2008; Gowda et al., 2010), the structure of N-(2,4-Dichlorophenyl)benzenesulfonamide (I) has been determined. The asymmetric unit of the structure contains two independent molecules.

The sulfonyl benzene and the aniline benzene rings in the two molecules of (I) are tilted relative to each other by 70.8 (1)° (molecule 1) and 74.8 (1)° (molecule 2). The other bond parameters in (I) are similar to those observed in other aryl sulfonamides (Gowda et al., 2010; Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, both the intramolecular N—H···Cl and intermolecular N—H···O hydrogen bonds are observed. The pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers (Fig. 2).

Experimental

The solution of benzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual benzenesulfonylchloride was treated with 2,4-dichloroaniline in the stoichiometric amounts and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2,4-dichlorophenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Shetty & Gowda, 2005). The rod like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by evaporating it at room temperature.