N-(3-Methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810002291

. 2010 Jan 23;66(Pt 2):o434. doi: 10.1107/S1600536810002291

N-(3-Methylphenyl)benzenesulfonamide

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

PMCID: PMC2979874 PMID: 21579849

Abstract

The asymmetric unit of the title compound, C₁₃H₁₃NO₂S, contains two independent molecules. The dihedral angles between the two aromatic rings are 67.9 (1) and 68.6 (1)° in the two molecules. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 ▶). For related structures, see: Gelbrich et al. (2007 ▶; Gowda et al. (2008 ▶); Nirmala et al. (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C₁₃H₁₃NO₂S
M _r = 247.30
Orthorhombic,
a = 8.787 (1) Å
b = 8.884 (1) Å
c = 32.406 (3) Å
V = 2529.7 (5) Å³
Z = 8
Cu Kα radiation
μ = 2.19 mm⁻¹
T = 299 K
0.60 × 0.60 × 0.35 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.353, T _max = 0.514
3284 measured reflections
3109 independent reflections
3002 reflections with I > 2σ(I)
R _int = 0.039
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.096
S = 1.01
3109 reflections
316 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ▶), 507 Friedel pairs
Flack parameter: −0.010 (17)

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, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002291/bt5172sup1.cif

e-66-0o434-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002291/bt5172Isup2.hkl

e-66-0o434-Isup2.hkl^{(152.6KB, 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⋯O1ⁱ	0.87 (3)	2.08 (3)	2.919 (3)	162 (3)
N2—H2N⋯O3ⁱⁱ	0.82 (3)	2.17 (3)	2.981 (3)	178 (3)

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

In the present work, as a part of studying the effect of substituents on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008; Nirmala et al., 2009), the structure of N-(3-methylphenyl)benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains two independent molecules (Fig. 1). The conformations of the N—H bonds are syn to the meta- methyl groups in the aniline benzene rings, in contrast to the anti conformation observed with respect to the ortho-methyl group in N-(2-methylphenyl)benzenesulfonamide (II), to the meta-chloro group in N-(3-chlorophenyl)benzenesulfonamide(III)(Gowda et al., 2008) and to the meta-methyl group in 4-methyl-N-(3-methylphenyl)benzenesulfonamide (IV) (Nirmala et al., 2009).

The two benzene rings in (I) are tilted relative to each other by 67.9 (1)° in molecule 1 and 68.6 (1)° in molecule 2, compared to the values of 61.5 (1)° in (II), 65.4 (1)° in (III) and 83.9 (1)° in (IV),

The other bond parameters are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing stabilized by intermolecular N—H···O hydrogen bonds (Table 1) is shown in 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 m-toluidine in the stoichiometric ratio 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-(3-methylphenyl)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).

The single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.