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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 [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 13.2
Details
Open access

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

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-H...N hydrogen bond generating an S(6) ring motif. In the crystal, molecules are linked by pairs of N-H...N and weak C-H...S hydrogen bonds to form inversion dimers.

Related literature

For a general background to the biological activity of thiourea, see: Koketsu & Ishihara (2006[Koketsu, M. & Ishihara, H. (2006). Curr. Org. Synth. 3, 439-455.]). For heterocyclic derivatives, metal complexes and molecular electronics, see: Zeng et al. (2003[Zeng, R.-S., Zou, S.-J. & Shen, Q. (2003). Org. Lett. 5, 1657-1659.]); D'hooghe et al. (2005[D'hooghe, M., Waterinckx, A. & De Kimpe, N. (2005). J. Org. Chem. 70, 227-232.]); 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.]); Duque et al. (2009[Duque, J., Estevez-Hernandez, O., Reguera, E., Ellena, J. & Correa, R. S. (2009). J. Coord. Chem. 62, 2804-2813.]). For related structures, see: Singh et al. (2012[Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012). Acta Cryst. E68, o2882-o2883.]); Koch (2001[Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.]); Hassan et al. (2007[Hassan, N. N. N., Kadir, M. A., Yusof, M. S. M. & Yamin, B. M. (2007). Acta Cryst. E63, o4224.]); Pérez et al. (2008[Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o513.]); Yan & Xue (2008[Yan, L. & Xue, S.-J. (2008). Chin. J. Struct. Chem. 27, 543-546.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N4O2S

  • Mr = 248.26

  • Monoclinic, P 21 /n

  • a = 5.6962 (2) Å

  • b = 21.0530 (7) Å

  • c = 8.7901 (3) Å

  • [beta] = 95.559 (3)°

  • V = 1049.17 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.421, Tmax = 1.000

  • 6957 measured reflections

  • 2028 independent reflections

  • 1951 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.108

  • S = 1.04

  • 2028 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...N3 0.86 1.89 2.6240 (18) 142
N2-H2B...N4i 0.86 2.21 3.0726 (19) 175
C10-H10A...S1i 0.93 2.76 3.5536 (17) 144
Symmetry code: (i) -x+2, -y+1, -z+1.

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


Acta Cryst (2012). E68, o3300-o3301   [ doi:10.1107/S1600536812044029 ]

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