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Volume 68 
Part 11 
Page o3142  
November 2012  

Received 11 August 2012
Accepted 5 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.161
Data-to-parameter ratio = 19.4
Details
Open access

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin 9054, New Zealand
Correspondence e-mail: iuklodhi@yahoo.com

In the title compound C11H17NO4S, an intramolecular O-H...O hydrogen bond forms an S(8) ring and determines the conformation of the bis(2-hydroxyethyl) segment of the molecule, holding the two CH2CH2OH groups close to coplanar (r.m.s. deviation = 0.185 Å). In the crystal, O-H...O hydrogen bonds link the molecules into zigzag chains along the b axis. Weaker additional C-H...O and C-H...[pi] contacts generate a three dimensional network, with molecules stacked along the b-axis direction.

Related literature

For pharmaceutical background to sulfonamides, see: Casini et al. (2002[Casini, A., Scozzafava, A., Mastrolorenzo, A. & Supuran, L. T. (2002). Curr. Cancer Drug Targets, 2, 55-75.]); Chambers & Jawetz (1998[Chambers, H. F. & Jawetz, E. (1998). Sulfonamides, trimethoprim, and quinolones, in basic and clinical pharmacology, edited by B. G. Katzung, pp. 761-763. Stamford: Appleton-Lange.]). For an alternative synthesis, see: Hori et al. (2011[Hori, Y., Pei, N., Kumagai, R. & Sasanuma, Y. (2011). Polym. Chem. 2, 2183-2185.]). For a related structure, see: Yoon et al. (2001[Yoon, I., Park, K.-M. & Lee, S. S. (2001). Acta Cryst. C57, 321-322.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]) and for hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H17NO4S

  • Mr = 259.32

  • Orthorhombic, P b c a

  • a = 17.9308 (5) Å

  • b = 7.1881 (2) Å

  • c = 19.8333 (6) Å

  • V = 2556.28 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.16 × 0.12 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 3124 measured reflections

  • 3124 independent reflections

  • 2343 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.161

  • S = 0.99

  • 3124 reflections

  • 161 parameters

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
O4-H4O...O3 0.76 (7) 1.89 (7) 2.634 (3) 166 (7)
O3-H3O...O4i 0.75 (4) 1.92 (4) 2.661 (3) 172 (4)
C10-H10A...O1ii 0.97 2.61 3.361 (3) 135
C3-H3...Cg1iii 0.93 2.78 3.522 (2) 138
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2181 ).


Acknowledgements

The authors acknowledge Mr Ejaz for his kind assistance with the X-ray data collection.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Casini, A., Scozzafava, A., Mastrolorenzo, A. & Supuran, L. T. (2002). Curr. Cancer Drug Targets, 2, 55-75.  [CrossRef] [PubMed] [ChemPort]
Chambers, H. F. & Jawetz, E. (1998). Sulfonamides, trimethoprim, and quinolones, in basic and clinical pharmacology, edited by B. G. Katzung, pp. 761-763. Stamford: Appleton-Lange.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hori, Y., Pei, N., Kumagai, R. & Sasanuma, Y. (2011). Polym. Chem. 2, 2183-2185.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yoon, I., Park, K.-M. & Lee, S. S. (2001). Acta Cryst. C57, 321-322.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3142  [ doi:10.1107/S1600536812041682 ]

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