N-(3-Eth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

Aziz-ur-Rehman; Asia Siddiqa; Mehmet Akkurt; Muhammad Athar Abbasi; Muhammad Jahangir; Islam Ullah Khan

doi:10.1107/S1600536810022427

. 2010 Jun 16;66(Pt 7):o1682. doi: 10.1107/S1600536810022427

N-(3-Ethoxyphenyl)-4-methylbenzenesulfonamide

Aziz-ur-Rehman ^a,^‡, Asia Siddiqa ^a, Mehmet Akkurt ^b,^*, Muhammad Athar Abbasi ^a, Muhammad Jahangir ^a, Islam Ullah Khan ^a

PMCID: PMC3006737 PMID: 21587907

Abstract

In the title compound, C₁₅H₁₇NO₃S, the two aromatic rings make a dihedral angle of 69.42 (9)° with each other and the bridging C—N—S—C torsion angle is 65.76 (16)°. Weak intramolecular C—H⋯O interactions may affect the molecular conformation. Two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H⋯O interactions, forming an R ₂ ²(8) ring motif. Furthermore, two intermolecular C—H⋯π interactions contribute to the stability of the crystal packing.

Related literature

For the biological activity of sulfonamides, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₃S
M _r = 291.37
Monoclinic,
a = 8.4612 (3) Å
b = 13.1862 (5) Å
c = 13.4237 (4) Å
β = 99.326 (2)°
V = 1477.90 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.34 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
13221 measured reflections
3608 independent reflections
2532 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.00
3608 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.31 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/S1600536810022427/sj5019sup1.cif

e-66-o1682-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022427/sj5019Isup2.hkl

e-66-o1682-Isup2.hkl^{(176.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4⋯O2	0.93	2.54	2.914 (2)	104
C13—H13⋯O1	0.93	2.42	3.019 (2)	122
C14—H14A⋯Cg1ⁱⁱ	0.97	2.90	3.752 (3)	147
C15—H15C⋯Cg2ⁱⁱⁱ	0.96	2.96	3.763 (3)	147

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

Acknowledgments

The authors are grateful to the Higher Education Commission for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamide is an important functionality found in a number of synthetic as well as natural compounds possessing versatile type of biological activities e.g. herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Soledade et al., 2006; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002) activities. In the present paper, the structure of N-(3-ethoxyphenyl)-4-methylbenzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the title compound (I), Fig. 1), the dihedral angle between the two aromatic rings (C2–C7 and C8–C13) is 69.42 (9)° and the bridging C5—S1—N1—C8 torsion angle is 65.76 (16)°. In the crystal structure, two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H···O interactions, forming an R₂²(8) ring motif (Table 1, Fig. 2).

In the structure, two intermolecular C—H···π interactions contribute to the stability of crystal packing (Table 1).

Experimental

A mixture of 4-methyl benzene sulfonyl chloride (10.0 mmoles; 1.90 g), 3-ethoxy aniline (meta-phenetidine) (10.0 mmoles; 1.25 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature. The crude mixture was washed with water and dried. Product was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 72%. 4-Methyl benzene sulfonyl chloride and meta-phenetidine were purchased from Sigma Aldrich while all other chemicals involved were obtained from Merk, Germany.