3-[(Furan-2-yl)carbon­yl]-1-(pyrimi­din-2-yl)thio­urea

Singh, D.P.; Pratap, S.; Gupta, S.K.; Butcher, R.J.

doi:10.1107/S1600536812044029

Volume 68
Part 12
Pages o3300-o3301
December 2012

Received 17 October 2012
Accepted 23 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 13.2
Details

3-[(Furan-2-yl)carbonyl]-1-(pyrimidin-2-yl)thiourea

Durga P. Singh,^a Seema Pratap,^a Sushil K. Gupta ^b and Ray J. Butcher ^c ^*

^aDepartment of Chemistry, M.M.V., Banaras Hindu University, Varanasi 221 005, India,^bSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: rbutcher99@yahoo.com

The title compound, C₁₀H₈N₄O₂S, was synthesized from furoyl isothiocynate and 2-aminopyrimidine in dry acetone. The two N-H groups are in an anti conformation with respect to each other and one N-H group is anti to the C=S group while the other is syn. The amide C=S and the C=O groups are syn to each other. The mean plane of the central thiourea fragment forms dihedral angles of 13.50 (14) and 5.03 (11)° with the furan and pyrimidine rings, respectively. The dihedral angle between the furan and pyrimidine rings is 18.43 (10)°. The molecular conformation is stabilized by an intramolecular N-HN hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked by pairs of N-HN and weak C-HS hydrogen bonds to form inversion dimers.

Related literature

For a general background to the biological activity of thiourea, see: Koketsu & Ishihara (2006). For heterocyclic derivatives, metal complexes and molecular electronics, see: Zeng et al. (2003); D'hooghe et al. (2005); Aly et al. (2007); Duque et al. (2009). For related structures, see: Singh et al. (2012); Koch (2001); Hassan et al. (2007); Pérez et al. (2008); Yan & Xue (2008).

Experimental

Crystal data

C₁₀H₈N₄O₂S
M_r = 248.26
Monoclinic, P 2₁ /n
a = 5.6962 (2) Å
b = 21.0530 (7) Å
c = 8.7901 (3) Å
= 95.559 (3)°
V = 1049.17 (6) Å³
Z = 4
Cu K radiation
= 2.74 mm^-1
T = 123 K
0.40 × 0.22 × 0.11 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.421, T_max = 1.000
6957 measured reflections
2028 independent reflections
1951 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.108
S = 1.04
2028 reflections
154 parameters
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BN3	0.86	1.89	2.6240 (18)	142
N2-H2BN4ⁱ	0.86	2.21	3.0726 (19)	175
C10-H10AS1ⁱ	0.93	2.76	3.5536 (17)	144
Symmetry code: (i) -x+2, -y+1, -z+1.

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: LH5548 ).

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. SKG wishes to acknowledge the USIEF for the award of a Fulbright-Nehru Senior Research Fellowship.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Aly, A. A., Ahmed, E. K., El-Mokadem, K. M. & Hegazy, M. E. F. (2007). J. Sulfur Chem. 28, 73-93.
D'hooghe, M., Waterinckx, A. & De Kimpe, N. (2005). J. Org. Chem. 70, 227-232.
Duque, J., Estevez-Hernandez, O., Reguera, E., Ellena, J. & Correa, R. S. (2009). J. Coord. Chem. 62, 2804-2813.
Hassan, N. N. N., Kadir, M. A., Yusof, M. S. M. & Yamin, B. M. (2007). Acta Cryst. E63, o4224.
Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.
Koketsu, M. & Ishihara, H. (2006). Curr. Org. Synth. 3, 439-455.
Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o513.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012). Acta Cryst. E68, o2882-o2883.
Yan, L. & Xue, S.-J. (2008). Chin. J. Struct. Chem. 27, 543-546.
Zeng, R.-S., Zou, S.-J. & Shen, Q. (2003). Org. Lett. 5, 1657-1659.

organic compounds