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Volume 68 
Part 12 
Page o3430  
December 2012  

Received 8 November 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.006 Å
R = 0.084
wR = 0.231
Data-to-parameter ratio = 24.2
Details
Open access

4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide

aDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Sanliurfa, Turkey,bCentral Research Lab, Harran University, Osmanbey Campus, 63300 Sanliurfa, Turkey,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Sanliurfa, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C11H15ClN2O3S, the 3-chloro-2,2-dimethylpropanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, molecules are linked by N-H...O and C-H...O hydrogen bonds, forming a three-dimensional network.

Related literature

For the antibacterial, antimicrobial and antiglaucoma activity of sulfonamides and their derivatives and for their physical properties and pharmacological applications, see: Poulsen et al. (2005[Poulsen, S., Bornaghi, L. F. & Healy, P. C. (2005). Bioorg. Med. Chem. Lett. 15, 5429-5433.]); Supuran & Scozzafava (2000[Supuran, C. T. & Scozzafava, A. (2000). Exp. Opin. Ther. Pat. 10, 575-600.]). For related structures, see: Akkurt et al. (2010[Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1559-o1560.]); Idemudia et al. (2012[Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1599.]); Asiri et al. (2012[Asiri, A. M., Faidallah, H. M., Alamry, K. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2258-o2259.]). For the synthesis, see: Türkmen et al. (2011[Türkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39 114-119.]).

[Scheme 1]

Experimental

Crystal data
  • C11H15ClN2O3S

  • Mr = 290.77

  • Monoclinic, P 21 /c

  • a = 20.4359 (11) Å

  • b = 7.2437 (4) Å

  • c = 9.4693 (5) Å

  • [beta] = 98.222 (3)°

  • V = 1387.35 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 294 K

  • 0.31 × 0.14 × 0.13 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: refined from [Delta]F (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.931, Tmax = 0.946

  • 4240 measured reflections

  • 4240 independent reflections

  • 2054 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.231

  • S = 1.02

  • 4240 reflections

  • 175 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.88 (3) 2.57 (5) 3.035 (4) 114 (4)
N1-H1N...O1ii 0.88 (3) 2.21 (4) 3.043 (5) 160 (5)
N1-H2N...O1iii 0.88 (2) 2.10 (4) 2.921 (4) 155 (5)
N2-H3N...O3iv 0.91 (6) 2.16 (6) 3.063 (5) 173 (5)
C11-H11B...O3iv 0.97 2.44 3.391 (5) 166
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: SJ5282 ).


Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 874 and 1136).

References

Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1559-o1560.  [CSD] [CrossRef] [details]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Asiri, A. M., Faidallah, H. M., Alamry, K. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2258-o2259.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1599.  [CSD] [CrossRef] [details]
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [ISI] [details]
Poulsen, S., Bornaghi, L. F. & Healy, P. C. (2005). Bioorg. Med. Chem. Lett. 15, 5429-5433.  [CrossRef] [PubMed] [ChemPort]
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Supuran, C. T. & Scozzafava, A. (2000). Exp. Opin. Ther. Pat. 10, 575-600.  [CrossRef] [ChemPort]
Türkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39 114-119.  [ISI] [PubMed]


Acta Cryst (2012). E68, o3430  [ doi:10.1107/S1600536812046806 ]

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