N-(2-Hy­droxy­phen­yl)-4-methyl­benzene­sulfonamide

Shaaban K Mohamed; Mehmet Akkurt; Benson M Kariuki; Ali M Ali; Mustafa R Albayati

doi:10.1107/S1600536813033394

. 2013 Dec 14;70(Pt 1):o54. doi: 10.1107/S1600536813033394

N-(2-Hydroxyphenyl)-4-methylbenzenesulfonamide

Shaaban K Mohamed ^a,^b, Mehmet Akkurt ^c, Benson M Kariuki ^d, Ali M Ali ^e, Mustafa R Albayati ^f,^*

PMCID: PMC3914092 PMID: 24526996

Abstract

In the title compound, C₁₃H₁₃NO₃S, the dihedral angle between the benzene rings is 64.15 (7)° and the C—S—N—C torsion angle is −57.18 (12)°. An intramolecular N—H⋯O hydrogen bond closes an S(5) ring. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(8) chains propagating in [100]. Weak C—H⋯π interactions are also observed.

Related literature

For background to the biological activity of sulfonamide compounds, see: Ozbek et al. (2007 ▶); El-Sayed et al. (2011 ▶). For related structures, see: Gowda et al. (2008a ▶,b ▶,c ▶). graphic file with name e-70-00o54-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₃NO₃S
M _r = 263.31
Monoclinic,
a = 7.6780 (1) Å
b = 15.4747 (3) Å
c = 10.7250 (2) Å
β = 104.333 (2)°
V = 1234.62 (4) Å³
Z = 4
Cu Kα radiation
μ = 2.34 mm⁻¹
T = 120 K
0.35 × 0.16 × 0.13 mm

Data collection

Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013 ▶) T _min = 0.494, T _max = 0.750
4355 measured reflections
2377 independent reflections
2248 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.082
S = 1.06
2377 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033394/hb7173sup1.cif

e-70-00o54-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033394/hb7173Isup2.hkl

e-70-00o54-Isup2.hkl^{(130.7KB, hkl)}

Click here for additional data file.^{(4.7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536813033394/hb7173Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.83 (2)	2.22 (2)	2.6420 (16)	111.6 (17)
O3—H1O⋯O2ⁱ	0.86 (2)	1.94 (2)	2.7852 (15)	172 (2)
C3—H3⋯Cg2ⁱⁱ	0.95	2.92	3.8022 (16)	155
C7—H7C⋯Cg1ⁱⁱⁱ	0.98	2.85	3.5937 (17)	134

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

Acknowledgments

We thank Manchester Metropolitan University, Erciyes University and Cardiff University for supporting this study.

supplementary crystallographic information

1. Comment

The biological activities of sulphonamide compounds are well documented, for example as antimicrobial (Ozbek et al., 2007) and anticancer (El-Sayed et al., 2011) agents. Further to our interest in related compounds with potential biactivity, we now report the synthesis and crystal structure of the title compound.

The benzene rings (C1–C6 and C8–C13) of the title compound (I) in Fig. 1 make a dihedral angle of 64.15 (7)° with each other. The bridge C1—S1—N1—C8 torsion angle between the benzene rings is -57.18 (12)°. The O1–S1–O2 and C1–S1–N1 angles are 119.78 (6) and 107.97 (6)°, respectively. The bond lengths and angles are similar to those in related structures (Gowda et al., 2008a,b,c).

The molecular conformation features an N—H···O hydrogen bond which forms an S(5) ring (Fig. 2). In the crystal, molecules are linked by O—H···O hydrogen bonds into C(8) chains along [100] (Figs. 2 and 3). Weak C—H···π interactions are also observed (Table 1).

2. Experimental

A mixture of 2-aminophenol (109 mg, 1 mmol) and p-toluenesulfonyl chloride (190 mg, 1 mmol) in 10 ml dioxane with addition of few drops of triethylamine as a catalyst, was refluxed for 4 h. The reaction mixture was left to cool at ambient temperature where the solid product was deposited, collected by filteration and recrystallized from ethanol in 91% yield. Brown needles were grown from ethanol solution over 3 days at room temperature. M.p. 391 K.