N-(4-Meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

Mehmet Akkurt; Irfana Mariam; Ifrah Naseer; Islam Ullah Khan; Shahzad Sharif

doi:10.1107/S1600536810052633

. 2010 Dec 18;67(Pt 1):o186. doi: 10.1107/S1600536810052633

N-(4-Methoxyphenyl)-4-methylbenzenesulfonamide

Mehmet Akkurt ^a,^*, Irfana Mariam ^b, Ifrah Naseer ^b, Islam Ullah Khan ^b,^*, Shahzad Sharif ^b

PMCID: PMC3050146 PMID: 21522690

Abstract

In the title compound, C₁₄H₁₅NO₃S, the dihedral angle between the aromatic rings is 59.39 (14)° and the C—S—N—C torsion angle is −71.4 (2)°. In the crystal, a supramolecular chain running along the b axis with a C(4) graph set is formed via N—H⋯O hydrogen bonds.

Related literature

For the biological activity of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For some structural studies of sulfonamides, see: Khan, Akkurt et al. (2010 ▶); Khan, Sharif et al. (2010 ▶); Sharif et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₅NO₃S
M _r = 277.34
Monoclinic, P2₁
a = 9.1777 (4) Å
b = 5.2179 (2) Å
c = 15.1621 (7) Å
β = 103.518 (2)°
V = 705.97 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.31 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
6858 measured reflections
2995 independent reflections
2175 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.106
S = 1.03
2995 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 1078 Freidel pairs
Flack parameter: 0.01 (8)

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/S1600536810052633/is2644sup1.cif

e-67-0o186-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052633/is2644Isup2.hkl

e-67-0o186-Isup2.hkl^{(147KB, 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—H1A⋯O2ⁱ	0.86	2.37	2.975 (3)	128

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The crystal structure of the title compound, (I), was determined in continuation of structural studies of sulfonamides (Sharif et al., 2010; Khan, Akkurt et al., 2010; Khan, Sharif et al., 2010), of interest owing to their enormous potential as biologically active molecules (Korolkovas, 1988; Mandell & Sande, 1992).

In the title compound (I), (Fig. 1), the dihedral angle between the two aromatic rings (C1–C6) and (C8–C13) is 59.39 (14)°. The molecule is twisted at the S atom with the C6—S1—N1—C8 torsion angle of -71.4 (2)°. The packing of molecules linked by of N—H···O hydrogen bonds (Table 1) form supramolecular chains [C(4) graph set; Bernstein et al., 1995] aligned along the b axis (Fig. 2).

Experimental

To para anisidine (123 mg, 1 mmol) in distilled water (10 ml) was added para toluene sulfonyl chloride (190 mg, 1 mmol) with stirring at room temperature while maintaining the pH of the reaction mixture at 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless needles (I) in 79% yield.