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Volume 69 
Part 5 
Page o798  
May 2013  

Received 15 April 2013
Accepted 20 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.106
Data-to-parameter ratio = 11.8
Details
Open access

5-Acetyl-3-(5-phenyl-1H-pyrazol-3-yl)-1,3,4-thiadiazol-2(3H)-one monohydrate

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, University of Gujrat, Gujrat 50700, Pakistan
Correspondence e-mail: mnachemist@hotmail.com, ghulam.mustafa@uog.edu.pk

In the title hydrate, C13H10N4O2S·H2O, the dihedral angles between the central pyrazole ring and its pendant phenyl and thiadiazole rings are 9.93 (8) and 4.56 (7)°, respectively. In the crystal, the components are linked by N-H...O, O-H...N and O-H...O hydrogen bonds, generating [100] chains incorporating R44(10) loops. A weak C-H...O interaction helps to consolidate the packing.

Related literature

For the synthesis of the title compound, see: Abdelhamid et al. (2001[Abdelhamid, A. O., Salam, M. M. M. & Amer, S. A. (2001). Heteroat. Chem. 12, 468-474.]). For a related structure, see: Ge (2006[Ge, W.-Z. (2006). Acta Cryst. E62, o3109-o3110.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N4O2S·H2O

  • Mr = 304.33

  • Monoclinic, P 21 /n

  • a = 7.6084 (2) Å

  • b = 25.5788 (4) Å

  • c = 7.6524 (2) Å

  • [beta] = 111.974 (3)°

  • V = 1381.07 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.25 mm-1

  • T = 296 K

  • 0.35 × 0.19 × 0.06 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.778, Tmax = 1.000

  • 10797 measured reflections

  • 2806 independent reflections

  • 2498 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.106

  • S = 1.07

  • 2806 reflections

  • 238 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.23 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-H1...O3Wi 0.93 (2) 1.83 (2) 2.749 (2) 173 (2)
O3W-H3A...N2ii 0.86 (3) 1.99 (3) 2.8402 (19) 169 (2)
O3W-H3B...O1iii 0.83 (5) 2.19 (5) 2.995 (2) 163 (4)
C8-H8...O1iv 0.93 (2) 2.50 (2) 3.4100 (19) 167.8 (15)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7073 ).


Acknowledgements

The authors thank the deanship of scientific research at King Abdulaziz University for the support of this research via Research Group Track of Grant No. (3-102/428).

References

Abdelhamid, A. O., Salam, M. M. M. & Amer, S. A. (2001). Heteroat. Chem. 12, 468-474.  [CrossRef] [ChemPort]
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ge, W.-Z. (2006). Acta Cryst. E62, o3109-o3110.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o798  [ doi:10.1107/S1600536813010817 ]

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