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Volume 70 
Part 1 
Page o54  
January 2014  

Received 9 December 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.082
Data-to-parameter ratio = 13.8
Details
Open access

N-(2-Hy­droxy­phen­yl)-4-methyl­benzene­sulfonamide

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales,eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

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...[pi] inter­actions are also observed.

Related literature

For background to the biological activity of sulfonamide compounds, see: Ozbek et al. (2007[Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105-5109.]); El-Sayed et al. (2011[El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.]). For related structures, see: Gowda et al. (2008a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.],b[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825.],c[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64, o2190.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO3S

  • Mr = 263.31

  • Monoclinic, P 21 /c

  • a = 7.6780 (1) Å

  • b = 15.4747 (3) Å

  • c = 10.7250 (2) Å

  • [beta] = 104.333 (2)°

  • V = 1234.62 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.494, Tmax = 0.750

  • 4355 measured reflections

  • 2377 independent reflections

  • 2248 reflections with I > 2[sigma](I)

  • Rint = 0.011

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.082

  • S = 1.06

  • 2377 reflections

  • 172 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

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
Symmetry codes: (i) x-1, y, z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2013[Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7173 ).


Acknowledgements

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

References

El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714-3720.  [Web of Science] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1691.  [CSD] [CrossRef] [IUCr Journals]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825.  [CSD] [CrossRef] [IUCr Journals]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008c). Acta Cryst. E64, o2190.  [CSD] [CrossRef] [IUCr Journals]
Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105-5109.  [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o54  [ doi:10.1107/S1600536813033394 ]

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