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Volume 68 
Part 12 
Page o3481  
December 2012  

Received 20 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
R = 0.073
wR = 0.178
Data-to-parameter ratio = 15.7
Details
Open access

4-[3-(4-Methylpiperidin-1-yl)propanamido]benzenesulfonamide monohydrate

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

In the title compound, C15H23N3O3S·H2O, the piperidine ring has a chair conformation. In the crystal, the sulfonamide molecules are linked by N-H...O hydrogen bonds, forming a layer parallel to (10-1). The layers are interconnected via N-H...Ow, Ow-H...N and Ow-H...O (w = water) hydrogen bonds, forming a three-dimensional network.

Related literature

For inhibitors of carbonic anhydrase enzyme, inhibitors of cysteine protease enzyme, the antibacterial and antimicrobial activity and physical properties of sulfonamides and their derivatives and for their pharmacological applications, see: 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.]); 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 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, o1596.],b[Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1596.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C15H23N3O3S·H2O

  • Mr = 343.45

  • Monoclinic, P 21 /n

  • a = 11.3200 (3) Å

  • b = 7.4068 (3) Å

  • c = 20.7937 (8) Å

  • [beta] = 96.787 (2)°

  • V = 1731.23 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 294 K

  • 0.24 × 0.15 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: part of the refinement model ([Delta]F) (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.951, Tmax = 0.975

  • 36305 measured reflections

  • 3540 independent reflections

  • 2259 reflections with I > 2[sigma](I)

  • Rint = 0.166

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.178

  • S = 1.02

  • 3540 reflections

  • 225 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1NA...O1i 0.88 (3) 2.17 (4) 2.971 (4) 150 (4)
N1-H1NB...O3ii 0.87 (3) 2.18 (3) 3.035 (4) 168 (3)
N2-H2N...O1W 0.89 (3) 1.99 (3) 2.871 (4) 176 (3)
O1W-HWA...O2iii 0.83 (3) 2.23 (2) 3.037 (3) 165 (4)
O1W-HWB...N3iv 0.84 (2) 1.95 (2) 2.783 (4) 174 (5)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) -x, -y, -z.

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: IS5222 ).


Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 348 and 1136).

References

Akkurt, M., Yalçin, S. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1596.  [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]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [ISI] [details]
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]
Yalçin, S. P., Akkurt, M., Durgun, M., Türkkan, B. & Türkmen, H. (2012). Acta Cryst. E68, o3430.  [CrossRef] [details]


Acta Cryst (2012). E68, o3481  [ doi:10.1107/S1600536812048477 ]

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