N-Ethyl-N-(4-methyl­phen­yl)benzene­sulfonamide

Muhammad Akhyar Farrukh; Komal Faryal; Maymoona Mahboob; Fahim Ashraf Qureshi; Mehmet Akkurt

doi:10.1107/S1600536812000177

. 2012 Jan 11;68(Pt 2):o326. doi: 10.1107/S1600536812000177

N-Ethyl-N-(4-methylphenyl)benzenesulfonamide

Muhammad Akhyar Farrukh ^a,^‡, Komal Faryal ^a, Maymoona Mahboob ^a, Fahim Ashraf Qureshi ^a, Mehmet Akkurt ^b,^*

PMCID: PMC3275014 PMID: 22346959

Abstract

The title compound, C₁₅H₁₇NO₂S, is twisted at the S—N bond with a C—S—N—C torsion angle of 73.90 (14)°. The dihedral angle between the aromatic rings is 36.76 (11)°.

Related literature

For related structures, see: Ahmad et al. (2011 ▶); Nirmala et al. (2011 ▶). For applications of sulfonamides, see: Faidallah et al. (2007 ▶); Gauss & Weinstein (1946 ▶); Korolkovas (1988 ▶); Laurence (2009 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M _r = 275.37
Orthorhombic,
a = 15.6737 (5) Å
b = 8.2831 (2) Å
c = 22.3326 (7) Å
V = 2899.37 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.20 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
26615 measured reflections
3592 independent reflections
2558 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.136
S = 1.02
3592 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.37 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 datablock(s) global, I. DOI: 10.1107/S1600536812000177/is5044sup1.cif

e-68-0o326-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000177/is5044Isup2.hkl

e-68-0o326-Isup2.hkl^{(176.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000177/is5044Isup3.cml

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

Acknowledgments

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University Lahore.

supplementary crystallographic information

Comment

Sulfonamides commonly named as Sulfa drugs are the medicines capable of controlling the bacterial infections (Laurence, 2009). The phenolic azo- dyes derived from the sulfonamides have the therapeutic potentialities and special mode of action against the acute bacterial infections (Korolkovas, 1988). Some benzenesulfonamide are evaluated for their in vitro antitumor activity (Faidallah et al., 2007). Hemorrhagic colitis (i.e. swollen of Colon and diarrhea) can be the direct result of the toxic effect of the ingested sulfonamide but with the withdrawal of the sulfonamides from the body, the symptoms subsided and body returns to its normal activity (Gauss & Weinstein, 1946) As part of our ongoing studies of the effect of substitutions on the structures of N-(aryl)-arylsulfonamides (Ahmad et al., 2011), we synthesized the title compound, (I), and report herein its crystal structure.

As shown in Fig. 1, the title molecule is twisted at the S—N bond with the C10—S1—N1—C5 torsion angle of 73.90 (14)°, compared to the values of 80.2 (3)° (molecule 1) and -79.4 (3)° (molecule 2) in N-ethyl-4-methyl-N-(3-methylphenyl)benzenesulfonamide (II) (Ahmad et al., 2011), -58.4 (2) and -48.3 (2)° (molecule 1) and -75.7 (3)° (molecule 2), in the two molecules of 2,4-dimethyl-N-(4-methylphenyl)benzenesulfonamide (III) (Nirmala et al., 2011). The phenyl and benzene rings in (I) are tilted relative to each other by 36.76 (11)°, compared to the values of 35.3 (2)° (molecule 1) and 42.5 (2)° (molecule 2) in (II), and 72.0 (1)° (molecule 1) and 78.3 (1)° (molecule 2) in (III). No classical hydrogen bonds are observed in the crystal structure. The crystal packing of (I) is shown in Figs. 2 & 3 down the a and b axes, respectively.

Experimental

5 mM of p-toluidine was dissolved in 20 ml of distilled water then 5 mM of ethyl iodide was added. The reaction mixture was stirred properly and 5 mM of benzenesulfonyl chloride was added. The mixture was stirred for about 1–2 h and the pH was maintained 8–10 using 3% Na₂CO₃ solution. The reaction was monitored by TLC. The product obtained was filtered and the precipitate was washed with distilled water, dried and recrystallized using methanol.