4-Methyl-N-(4-methyl­phen­yl)benzene­sulfonamide

Islam Ullah Khan; Shahzad Sharif; Mehmet Akkurt; Arif Sajjad; Jamil Ahmad

doi:10.1107/S1600536810008329

. 2010 Mar 10;66(Pt 4):o786. doi: 10.1107/S1600536810008329

4-Methyl-N-(4-methylphenyl)benzenesulfonamide

Islam Ullah Khan ^a,^‡, Shahzad Sharif ^a, Mehmet Akkurt ^b,^*, Arif Sajjad ^a, Jamil Ahmad ^a

PMCID: PMC2983966 PMID: 21580625

Abstract

In the title compound, C₁₄H₁₅NO₂S, the two aromatic rings enclose a dihedral angle of 70.53 (10)°. A weak intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Deng & Mani (2006 ▶). For the biological activity of sulfonamides, see: Pandya et al. (2003 ▶); Supuran & Scozzafava (2000 ▶). For the effects of substituents on the crystal structures of and bond lengths in aryl sulfonamides, see: Sharif et al. (2010 ▶); Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶); Nirmala et al. (2009a ▶,b ▶)·For graph-set notation, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M _r = 261.34
Triclinic,
a = 8.6419 (8) Å
b = 8.8016 (8) Å
c = 9.2509 (7) Å
α = 88.187 (4)°
β = 77.010 (4)°
γ = 74.812 (4)°
V = 661.41 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.28 × 0.17 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
11831 measured reflections
3259 independent reflections
2323 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.122
S = 1.01
3259 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008329/bt5205sup1.cif

e-66-0o786-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008329/bt5205Isup2.hkl

e-66-0o786-Isup2.hkl^{(159.8KB, 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—H1⋯O2ⁱ	0.81 (3)	2.11 (3)	2.904 (2)	170 (2)
C4—H4⋯O1	0.93	2.45	3.049 (2)	122

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Mr Muhammad Hussain of Bana International for providing technical support to the Materials Chemistry Laboratory, Government College University.

supplementary crystallographic information

Comment

Sulfonamides are well known for their antibacterial and enzyme inhibitor properties (Pandya et al., 2003). Aromatic sulfonamides were also reported to inhibit the growth of tumor cells (Supuran & Scozzafava, 2000). In continuation of our studies (Sharif et al., 2010), herein, we report the crystal structure of the title compound.

The title molecule (I), (Fig. 1), is bent at the N atom with the C8—SO₂—NH—C5 torsion angle of -60.71 (18)°. The dihedral angle between the two aromatic rings is 70.53 (10)°.

The molecular conformation of the title compound is stabilized by a weak intramolecular C—H···O hydrogen bond, generating an S(6) ring motif (Etter, 1990; Bernstein et al., 1995) (Table 1). In the crystal structure of the title compound, inversion-related molecules are linked into dimers by pairs of N—H···O hydrogen bonds, forming an R₂²(8) graph-set motif (Table 1 and Fig. 2).

Experimental

The synthesis of the title compound was performed by the procedure reported by Deng & Mani (2006). 4-methyl aniline 0.535 g (5 mmol) was dissolved in 10 ml distilled water and pH of the solution was adjusted to 8 by using (3 M) Na₂CO₃. p-toluene sulfonyl chloride 0.95 g (5 mmol) was added under continuous stirring at room temperature. pH of the reaction mixture during stirring was maintained between 8-9 with 3 M Na₂CO₃. When the solution was clear, pH was adjusted to 2-3 using 3 M HCl. The precipitate formed was filtered and recrystallized from methanol.