N-(3-Chloro­phen­yl)benzene­sulfonamide

B Thimme Gowda; Sabine Foro; K S Babitha; Hartmut Fuess

doi:10.1107/S1600536808026895

. 2008 Aug 23;64(Pt 9):o1825. doi: 10.1107/S1600536808026895

N-(3-Chlorophenyl)benzenesulfonamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, K S Babitha ^a, Hartmut Fuess ^b

PMCID: PMC2960722 PMID: 21201800

Abstract

In the crystal structure of the title compound, C₁₂H₁₀ClNO₂S, the N—H bond is trans to one of the S=O bonds. The two aromatic rings form a dihedral angle of 65.4 (1)°, compared with a value of 49.1 (1)° in N-(2-chlorophenyl)-benzenesulfonamide. The molecules are connected by intermolecular N—H⋯O hydrogen bonds into chains running along the b axis.

Related literature

For related literature, see: Gelbrich et al. (2007 ▶); Gowda et al. (2005 ▶, 2008a ▶,b ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₁₀ClNO₂S
M _r = 267.72
Tetragonal,
a = 8.8357 (7) Å
c = 32.081 (5) Å
V = 2504.6 (5) Å³
Z = 8
Cu Kα radiation
μ = 4.18 mm⁻¹
T = 299 (2) K
0.38 × 0.35 × 0.33 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.222, T _max = 0.251
5004 measured reflections
2232 independent reflections
2054 reflections with I > 2σ(I)
R _int = 0.071
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.094
S = 1.10
2232 reflections
158 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 840 Friedel pairs
Flack parameter: −0.01 (2)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026895/ci2659sup1.cif

e-64-o1825-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026895/ci2659Isup2.hkl

e-64-o1825-Isup2.hkl^{(109.8KB, 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	0.88 (1)	2.029 (13)	2.875 (2)	162 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of N-(aryl)-benzenesulfonamides, in the present work, the structure of N-(3-chlorophenyl)-benzenesulfonamide (N3CPBSA) has been determined (Gowda et al., 2008a,b). The N—H bond is trans to one of the S═O bonds (Fig. 1). Further, the conformation of the N—H bond is anti to the meta-chloro group in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho-chloro group in N-(2-chlorophenyl)-benzenesulfonamide (N2CPBSA) (Perlovich et al., 2006). The two benzene rings form a dihedral angle of 65.4 (1)° compared with the value of 49.1 (1)° in N2CPBSA. The other bond parameters in N3CPBSA are similar to those observed in N2CPBSA (Perlovich et al., 2006) and other N-(aryl)-benzenesulfonamides (Gelbrich et al., 2007; Gowda et al., 2008a,b).

The packing diagram of N3CPBSA showing the N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The solution of benzene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) at 273 K. 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 m-chloroaniline in the stoichiometric ratio and boiled for 10 min. The reaction mixture was then cooled to room temperature and added to ice cold water (100 cc). The resultant solid N-(3-chlorophenyl)-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 (Gowda et al., 2005). Single crystals used in X-ray diffraction studies were grown in an ethanolic solution by evaporating it at room temperature.