[Journal logo]

Volume 68 
Part 12 
Pages o3475-o3476  
December 2012  

Received 20 November 2012
Accepted 22 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.004 Å
R = 0.065
wR = 0.169
Data-to-parameter ratio = 23.5
Details
Open access

4-(5-Chloropentanamido)benzenesulfonamide

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

The molecular conformation of the title compound, C11H15ClN2O3S, is stabilized by a C-H...O hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by two pairs of inversion-related N-H...O hydrogen bonds, generating R22(8) and R22(20) ring motifs, resulting in chains running along [0-11]. These chains are connected by N-H...O hydrogen bonds along [100], forming layers parallel to (011). There are also C-H...[pi] interactions between the layers, which consolidate the three-dimensional structure.

Related literature

Sulfonamides represent an important class of biologically active compounds. For their action as inhibitors of carbonic anhydrase enzyme, their antibacterial properties in chemotherapy, as antithyroid drugs, and for their antimicrobial properties, see: Maren (1987[Maren, T. H. (1987). Drug Dev. Res. 10, 255-276.]); Supuran (2008[Supuran, C. T. (2008). Nat. Rev. Drug Discov. 7, 168-181.]); Turkmen et al. (2005[Turkmen, H., Durgun, M., Yilmaztekin, S., Emul, M., Innocenti, A., Vullo, D., Scozzafava, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 367-372.], 2011[Turkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39, 114-119.]); Rami et al. (2011[Rami, M., Innocenti, A., Montero, J. L., Scozzafava, A., Winum, J. Y. & Supuran, C. T. (2011). Bioorg. Med. Chem. Lett. 21, 5210-5213.]). For their antiviral properties, such as HIV protease inhibitors, see: De Clercq (2001[De Clercq, E. (2001). Curr. Med. Chem. 8, 1543-1572.]) and as inhibitors of cysteine protease enzyme, see: Danial & Korsmeyer (2004[Danial, N. N. & Korsmeyer, S. J. (2004). Cell, 116, 205-219.]). For related structures, see: Yalçin et al. (2012[Yalçin, S. P., Akkurt, M., Durgun, M., Türkkan, B. & Türkmen, H. (2012). Acta Cryst. E68, o3430.]); Akkurt et al. (2010a[Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1559-o1560.],b[Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1596.]). 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
  • C11H15ClN2O3S

  • Mr = 290.77

  • Triclinic, [P \overline 1]

  • a = 8.4872 (1) Å

  • b = 8.7730 (2) Å

  • c = 10.4572 (3) Å

  • [alpha] = 73.711 (4)°

  • [beta] = 85.281 (4)°

  • [gamma] = 63.393 (3)°

  • V = 667.37 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 294 K

  • 0.24 × 0.15 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.901, Tmax = 0.949

  • 20164 measured reflections

  • 4036 independent reflections

  • 2815 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.169

  • S = 1.05

  • 4036 reflections

  • 172 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C5-H5...O3 0.93 2.25 2.809 (4) 118
N1-H1NA...O3i 0.87 (2) 1.99 (3) 2.865 (3) 176 (3)
N1-H1NB...O1ii 0.87 (3) 2.11 (2) 2.963 (3) 166 (4)
N2-H2N...O2iii 0.88 (3) 2.17 (3) 3.021 (4) 166 (3)
C10-H10A...Cg1iv 0.97 2.96 3.771 (3) 142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y, -z+2; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1.

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: SU2531 ).


Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK Project Nos. 295 and 1136).

References

Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1559-o1560.  [CSD] [CrossRef] [details]
Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1596.  [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]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Danial, N. N. & Korsmeyer, S. J. (2004). Cell, 116, 205-219.  [ISI] [CrossRef] [PubMed] [ChemPort]
De Clercq, E. (2001). Curr. Med. Chem. 8, 1543-1572.  [ISI] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Maren, T. H. (1987). Drug Dev. Res. 10, 255-276.  [CrossRef] [ChemPort] [ISI]
Rami, M., Innocenti, A., Montero, J. L., Scozzafava, A., Winum, J. Y. & Supuran, C. T. (2011). Bioorg. Med. Chem. Lett. 21, 5210-5213.  [CrossRef] [ChemPort] [PubMed]
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. (2008). Nat. Rev. Drug Discov. 7, 168-181.  [ISI] [CrossRef] [PubMed] [ChemPort]
Turkmen, H., Durgun, M., Yilmaztekin, S., Emul, M., Innocenti, A., Vullo, D., Scozzafava, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 367-372.  [CrossRef] [PubMed] [ChemPort]
Turkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39, 114-119.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yalçin, S. P., Akkurt, M., Durgun, M., Türkkan, B. & Türkmen, H. (2012). Acta Cryst. E68, o3430.  [CrossRef] [details]


Acta Cryst (2012). E68, o3475-o3476   [ doi:10.1107/S1600536812048118 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.