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

Singh, D.P.; Pratap, S.; Yildirim, S. Ö.; Butcher, R.J.

doi:10.1107/S160053681204500X

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 (C-C) = 0.003 Å
R = 0.039
wR = 0.110
Data-to-parameter ratio = 15.0
Details

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

Durga Prasad Singh,^a Seema Pratap,^a Sema Öztürk Yildirim ^b and Ray J. Butcher ^c ^*

^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-HN hydrogen bonds. In addition the water O atom is further linked by N-HO 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-HO hydrogen bonds.

Related literature

For general background to aroylthiourea and its derivatives, see: Aly et al. (2007). For related structures, see: Koch (2001); Pérez et al. (2008). For their biological activity, see: Saeed et al. (2008); Gu et al. (2007); Xu et al. (2004); Yan & Xue (2008).

Experimental

Crystal data

C₉H₇N₃OS₃·0.5H₂O
M_r = 278.37
Triclinic, $[P \overline 1]$
a = 7.4489 (4) Å
b = 11.1060 (6) Å
c = 14.7935 (7) Å
= 93.559 (4)°
= 99.813 (4)°
= 107.789 (5)°
V = 1139.74 (11) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.441, T_max = 1.000
7828 measured reflections
4566 independent reflections
3906 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(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
_max = 0.43 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AAO1Wⁱ	0.86	2.22	3.003 (3)	152
N1B-H1BAO1Wⁱⁱ	0.86	2.14	2.973 (3)	163
N2A-H2AAO1A	0.86	1.89	2.599 (3)	138
N2B-H2BAO1B	0.86	1.90	2.588 (3)	136
O1W-H1WN3B	0.82 (1)	2.06 (1)	2.852 (3)	163 (4)
O1W-H2WN3A	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Gu, C.-L., Liu, L., Sui, Y., Zhao, J.-L. D., Wang, D. & Chen, Y.-J. (2007). Tetrahedron, 18, 455-463.
Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.
Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o695.
Saeed, S., Bhatti, M. H., Yunus, U. & Jones, P. G. (2008). Acta Cryst. E64, o1485.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xu, Y., Hua, W., Liu, X. & Zhu, D. (2004). Chin. J. Org. Chem. 24, 1217-1222.
Yan, L. & Xue, S.-J. (2008). Chin. J. Struct. Chem. 27, 543-546.

organic compounds