[Journal logo]

Volume 69 
Part 3 
Pages o330-o331  
March 2013  

Received 5 December 2012
Accepted 28 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 13.5
Details
Open access

1-(2-Furoyl)-3-(2-methoxy-4-nitrophenyl)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,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: rbutcher99@yahoo.com

The asymmetric unit of the title compound, C13H11N3O5S, contains two independent molecules, which are linked by a pair of intermolecular N-H...S hydrogen bonds, forming an R22(8) ring motif. The central thiourea core forms dihedral angles of 3.02 (12) and 14.00 (10)° with the essentially planar furoyl groups [maximum deviations = 0.030 (2) and 0.057 (2) Å] in the two molecules and dihedral angles of 2.43 (13) and 8.03 (12)° with the benzene rings. The dihedral angles between the furoyl and benzene rings in the two molecules are 3.97 (10) and 5.98 (9)°. The trans-cis geometry of the thiourea group is stabilized by three intramolecular N-H...O hydrogen bonds involving carbonyl and methoxy O atoms with the H atom of the cis-thioamide group and between furan O atom and the other thioamide H atom. There is also a weak intramolecular C-H...S interaction in each molecule.

Related literature

For background to anion receptors, see: Doyle & Jacobsen (2007[Doyle, A. G. & Jacobsen, E. N. (2007). Chem. Rev. 107, 5713-5743.]); Gale et al. (2008[Gale, P. A., García-Garrido, S. E. & Garric, J. (2008). Chem. Soc. Rev. 37, 151-190.]); Svetlana (2007[Svetlana, B. T. (2007). Eur. J. Org. Chem. 2007, 1701-1716.]). For aroyl thioureas as ionophores, see: Wilson et al. (2010[Wilson, D., Ángeles Arada, M. de los, Alegret, S. & Valle, M. del (2010). J. Hazard. Mater. 181, 140-146.]); Pérez et al. (2008[Pérez, H., Mascarenhas, Y., Estévez-Hernández, O., Santos Jr, S. & Duque, J. (2008). Acta Cryst. E64, o695.]) and as catalysts, see: Yang et al. (2004[Yang, D., Chen, Y.-C. & Zhu, N.-Y. (2004). Org. Lett. 6, 1577-1580.]); Dai et al. (2004[Dai, M., Liang, B., Wang, C., Chen, J. & Yang, Z. (2004). Org. Lett. 6, 221-224.]). 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.]); Singh et al. (2012a[Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012a). Acta Cryst. E68, o2882-o2883.],b[Singh, D. P., Pratap, S., Yildirim, S. Ö. & Butcher, R. J. (2012b). Acta Cryst. E68, o3295.],c[Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012c). Acta Cryst. E68, o3300-o3301.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3O5S

  • Mr = 321.31

  • Triclinic, [P \overline 1]

  • a = 7.9474 (6) Å

  • b = 13.0122 (10) Å

  • c = 13.4215 (11) Å

  • [alpha] = 87.734 (6)°

  • [beta] = 77.014 (7)°

  • [gamma] = 86.945 (7)°

  • V = 1350.00 (18) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.43 mm-1

  • T = 123 K

  • 0.69 × 0.21 × 0.04 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.441, Tmax = 0.909

  • 9239 measured reflections

  • 5400 independent reflections

  • 4064 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.03

  • 5400 reflections

  • 399 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AA...O1A 0.88 2.24 2.684 (2) 111
N2A-H2AA...O2A 0.88 1.91 2.654 (2) 142
N2A-H2AA...O3A 0.88 2.09 2.552 (2) 112
N1B-H1BA...O1B 0.88 2.25 2.683 (2) 111
N2B-H2BA...O2B 0.88 1.92 2.653 (2) 140
N2B-H2BA...O3B 0.88 2.11 2.554 (2) 111
C8A-H8AA...S1A 0.95 2.52 3.198 (2) 129
C8B-H8BA...S1B 0.95 2.52 3.189 (2) 128

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: 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: LH5568 ).


Acknowledgements

SP and DPS 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 (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Dai, M., Liang, B., Wang, C., Chen, J. & Yang, Z. (2004). Org. Lett. 6, 221-224.  [ISI] [CrossRef] [PubMed] [ChemPort]
Doyle, A. G. & Jacobsen, E. N. (2007). Chem. Rev. 107, 5713-5743.  [ISI] [CrossRef] [PubMed] [ChemPort]
Gale, P. A., García-Garrido, S. E. & Garric, J. (2008). Chem. Soc. Rev. 37, 151-190.  [ISI] [CrossRef] [PubMed] [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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012a). Acta Cryst. E68, o2882-o2883.  [CSD] [CrossRef] [details]
Singh, D. P., Pratap, S., Gupta, S. K. & Butcher, R. J. (2012c). Acta Cryst. E68, o3300-o3301.  [CSD] [CrossRef] [details]
Singh, D. P., Pratap, S., Yildirim, S. Ö. & Butcher, R. J. (2012b). Acta Cryst. E68, o3295.  [CSD] [CrossRef] [details]
Svetlana, B. T. (2007). Eur. J. Org. Chem. 2007, 1701-1716.
Wilson, D., Ángeles Arada, M. de los, Alegret, S. & Valle, M. del (2010). J. Hazard. Mater. 181, 140-146.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yang, D., Chen, Y.-C. & Zhu, N.-Y. (2004). Org. Lett. 6, 1577-1580.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o330-o331   [ doi:10.1107/S1600536813002894 ]

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.