[Journal logo]

Volume 68 
Part 12 
Page o3295  
December 2012  

Received 18 October 2012
Accepted 30 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.110
Data-to-parameter ratio = 15.0
Details
Open access

N-(1,3-Thiazol-2-yl)-N'-[(thiophen-2-yl)carbonyl]thiourea hemihydrate

aDepartment of Chemistry, M.M.V., Banaras Hindu University, Varanasi 221 005, India,bErciyes University, Faculty of Sciences, Department of Physics, 38039 Kayseri, Turkey, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: rbutcher99@yahoo.com

The title compound, C9H7N3OS3·0.5H2O, crystallizes with two independent but similar molecules in the asymmetric unit, both of which are linked by a water molecule through O-H...N hydrogen bonds. In addition the water O atom is further linked by N-H...O hydrogen bonds to two additional main molecules, forming a tetrameric unit. These tetrameric units then form infinite ribbons parallel to the ac plane.The dihedral angle between the thiophenoyl and thiazolyl rings is 12.15 (10) and 21.69 (11)° in molecules A and B, respectively. The central thiourea core makes dihedral angles of 5.77 (11) and 8.61 (9)°, respectively, with the thiophenoyl and thiazolyl rings in molecule A and 8.41 (10) and 13.43 (12)° in molecule B. Each molecule adopts a trans-cis geometry with respect to the position of thiophenoyl and thiazole groups relative to the S atom across the thiourea C-N bonds. This geometry is stabilized by intramolecular N-H...O hydrogen bonds.

Related literature

For general background to aroylthiourea and its derivatives, see: Aly et al. (2007[Aly, A. A., Ahmed, E. K., El-Mokadem, K. M. & Hegazy, M. E. F. (2007). J. Sulfur Chem. 28, 73-93.]). For related structures, see: Koch (2001[Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.]); Pérez et al. (2008[Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o695.]). For their biological activity, see: Saeed et al. (2008[Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008). Acta Cryst. E64, o1485.]); Gu et al. (2007[Gu, C.-L., Liu, L., Sui, Y., Zhao, J.-L. D., Wang, D. & Chen, Y.-J. (2007). Tetrahedron, 18, 455-463.]); Xu et al. (2004[Xu, Y., Hua, W., Liu, X. & Zhu, D. (2004). Chin. J. Org. Chem. 24, 1217-1222.]); Yan & Xue (2008[Yan, L. & Xue, S.-J. (2008). Chin. J. Struct. Chem. 27, 543-546.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7N3OS3·0.5H2O

  • Mr = 278.37

  • Triclinic, [P \overline 1]

  • a = 7.4489 (4) Å

  • b = 11.1060 (6) Å

  • c = 14.7935 (7) Å

  • [alpha] = 93.559 (4)°

  • [beta] = 99.813 (4)°

  • [gamma] = 107.789 (5)°

  • V = 1139.74 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 5.86 mm-1

  • T = 123 K

  • 0.35 × 0.25 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur (Ruby, Gemini CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.441, Tmax = 1.000

  • 7828 measured reflections

  • 4566 independent reflections

  • 3906 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.110

  • S = 1.08

  • 4566 reflections

  • 304 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AA...O1Wi 0.86 2.22 3.003 (3) 152
N1B-H1BA...O1Wii 0.86 2.14 2.973 (3) 163
N2A-H2AA...O1A 0.86 1.89 2.599 (3) 138
N2B-H2BA...O1B 0.86 1.90 2.588 (3) 136
O1W-H1W...N3B 0.82 (1) 2.06 (1) 2.852 (3) 163 (4)
O1W-H2W...N3A 0.82 (1) 2.09 (1) 2.892 (3) 167 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2240 ).


Acknowledgements

DPS and SP are grateful to Banaras Hindu University, Varanasi, for financial support. RJB acknowledges the NSF- MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Aly, A. A., Ahmed, E. K., El-Mokadem, K. M. & Hegazy, M. E. F. (2007). J. Sulfur Chem. 28, 73-93.  [CrossRef] [ChemPort]
Gu, C.-L., Liu, L., Sui, Y., Zhao, J.-L. D., Wang, D. & Chen, Y.-J. (2007). Tetrahedron, 18, 455-463.  [ChemPort]
Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.  [ISI] [CrossRef] [ChemPort]
Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o695.  [CSD] [CrossRef] [details]
Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008). Acta Cryst. E64, o1485.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xu, Y., Hua, W., Liu, X. & Zhu, D. (2004). Chin. J. Org. Chem. 24, 1217-1222.  [ChemPort]
Yan, L. & Xue, S.-J. (2008). Chin. J. Struct. Chem. 27, 543-546.  [ChemPort]


Acta Cryst (2012). E68, o3295  [ doi:10.1107/S160053681204500X ]

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.