N-(5-Chloro-2-meth­oxy­phen­yl)benzene­sulfonamide

Aziz-ur-Rehman; Shahzaman; Mehmet Akkurt; Muhammad Athar Abbasi; Islam Ullah Khan

doi:10.1107/S1600536810041206

. 2010 Oct 20;66(Pt 11):o2855. doi: 10.1107/S1600536810041206

N-(5-Chloro-2-methoxyphenyl)benzenesulfonamide

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

PMCID: PMC3009279 PMID: 21589040

Abstract

In the title compound, C₁₃H₁₂ClNO₃S, the dihedral angle between the two aromatic rings is 73.94 (9)°. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, intermolecular N—H⋯O hydrogen bonds connect the molecules to centrosymmetric dimers, forming an R ₂ ²(8) ring motif. The packing is consolidated by C—H⋯O hydrogen bonds and weak π–π interactions [centroid–centroid distances = 3.81 (3) and 3.81 (3) Å].

Related literature

For the biological properties of sulfonamide derivatives, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶). For related structures, see: Aziz-ur-Rehman et al. (2010a ▶,b ▶); Khan et al. (2010 ▶); Akkurt et al. (2010 ▶).

Experimental

Crystal data

C₁₃H₁₂ClNO₃S
M _r = 297.76
Triclinic,
a = 8.2201 (2) Å
b = 8.9395 (2) Å
c = 10.5544 (2) Å
α = 77.206 (1)°
β = 76.366 (1)°
γ = 66.408 (1)°
V = 683.65 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 296 K
0.24 × 0.16 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
12007 measured reflections
3333 independent reflections
2906 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.096
S = 1.02
3333 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 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/S1600536810041206/bt5375sup1.cif

e-66-o2855-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041206/bt5375Isup2.hkl

e-66-o2855-Isup2.hkl^{(163.5KB, 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⋯O1ⁱ	0.828 (16)	2.217 (16)	3.0096 (15)	160.2 (16)
C4—H4⋯O2ⁱⁱ	0.93	2.55	3.368 (3)	147
C8—H8⋯O2	0.93	2.34	2.9491 (17)	123
C13—H13B⋯O2ⁱⁱⁱ	0.96	2.48	3.362 (3)	153

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

Acknowledgments

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

supplementary crystallographic information

Comment

Sulfonamide is found in a number of synthetic as well as natural compounds. These molecules posses many 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). In the present paper, the structure of N-(5-chloro-2-methoxyphenyl) benzenesulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the title molecule (I), (Fig. 1), both sulfonamido-O atoms lie on the opposite side of the S-bound phenyl ring to the sulfonamido-N1 atom [the O1–S1–C1–C6, O2–S1–C1–C2 and N1–S1–C1–C2 torsion angles are -34.32 (13), 14.43 (13) and -101.83 (12) °, respectively]. The dihedral angle formed between the phenyl (C1–C6) and benzene (C7–C12) rings in (I) is 73.94 (9) °.

The molecules of (I) are dimerized due to the intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2) producing a R₂²(8) ring motif.

In addition, there are C—H···O hydrogen bonds, as well as π-π interactions [Cg1···Cg1(1 - x, -y, 2 - z) = 3.8163 (11) Å and cg2···Cg2(-x, 1 - y, 1 - z) = 3.9472 (12) Å; where Cg1 and Cg2 are centroids of the phenyl and benzene rings (C1–C6 and C7–C12), respectively], between the aromatic rings of each dimer.

Experimental

A mixture benzenesulfonyl chloride (10.0 mmol; 1.45 ml), 5-chloro-2-methoxy aniline (10.0 mmol; 1.47 g), aqueous sodium carbonate (10%; 20.0 ml) and water (25 ml) was stirred for one and half hour at room temperature. The crude mixture was washed with water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless crystal of N-(5-chloro-2-methoxyphenyl)benzenesulfonamide in 71% yield.