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Volume 69 
Part 8 
Pages o1244-o1245  
August 2013  

Received 1 July 2013
Accepted 5 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.088
Data-to-parameter ratio = 15.4
Details
Open access

Ethyl 3-amino-5-anilino-4-cyanothiophene-2-carboxylate

aChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt,eSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C14H13N3O2S, the dihedral angle between the thiophene and phenyl rings is 24.95 (8)°. The molecular structure is consolidated by intramolecular N-H...O and C-H...S interactions. The crystal structure features N-H...N and N-H...O hydrogen bonds forming centrosymmetric R22(12) dimers, which are linked into a two-dimensional network parallel to (011) with an S(6)R22S(6) motif. In addition, [pi]-[pi] stacking interactions [centroid-centroid distance = 3.7013 (12) Å] occur between the thiophene and phenyl rings of adjacent molecules.

Related literature

For pharmaceutical and industrial applications of amino-thiophene-containingg compounds, see: Inversen et al. (2000[Inversen, L. F., Anderson, H. S., Branner, S., Moretensen, S. P., Peters, G. H., Norris, K., Olsen, O. H., Jeppesen, C. B., Lundt, B. F., Ripka, W., Moller, K. B. & Moller, N. P. H. (2000). J. Biol. Chem. 275, 10300-10307.]); Webb et al. (2000[Webb, T. R., Melman, N., Lvovskiy, D., Ji, X. & Jacobson, K. A. (2000). Bioorg. Med. Chem. Lett. 10, 31-34.]). For the synthesis of multi-substituted thiphene compounds, see: El-Sharkawy et al. (2012[El-Sharkawy, K. A., El-Sayed, N. N. E. & Zaki, M. Y. (2012). Int. Res. J. Pure Appl. Chem. 2, 91-104.]); Huang et al. (2011[Huang, X.-G., Liu, J., Ren, J., Wang, T., Chen, W. & Zeng, B.-B. (2011). Tetrahedron, 67, 6202-6205.]). For the crystal structure of a related compound, see: Mabkhot et al. (2013[Mabkhot, Y. N., Alatibi, F., Barakat, A., Choudhary, M. I. & Yousuf, S. (2013). Acta Cryst. E69, o1049.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3O2S

  • Mr = 287.34

  • Monoclinic, P 21 /c

  • a = 8.6121 (15) Å

  • b = 10.6579 (15) Å

  • c = 14.328 (3) Å

  • [beta] = 92.580 (3)°

  • V = 1313.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 100 K

  • 0.55 × 0.04 × 0.03 mm

Data collection
  • Rigaku AFC12 (Right, Saturn724+) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.887, Tmax = 1.000

  • 8995 measured reflections

  • 2996 independent reflections

  • 2728 reflections with I > 2[sigma](I)

  • Rint = 0.025

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

  • wR(F2) = 0.088

  • S = 1.07

  • 2996 reflections

  • 194 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3NA...O2 0.87 (2) 2.25 (2) 2.8671 (19) 128.0 (17)
N1-H1N...N2i 0.84 (2) 2.23 (2) 3.026 (2) 158.1 (16)
N3-H3NB...O2ii 0.86 (2) 2.24 (2) 3.0985 (18) 175.9 (17)
C10-H10...S1 0.95 2.55 3.1463 (17) 121
Symmetry codes: (i) -x, -y+2, -z; (ii) [-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2639 ).


Acknowledgements

Erciyes University, Sohag University and Southampton University are gratefully acknowledged for supporting this study.

References

El-Sharkawy, K. A., El-Sayed, N. N. E. & Zaki, M. Y. (2012). Int. Res. J. Pure Appl. Chem. 2, 91-104.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Huang, X.-G., Liu, J., Ren, J., Wang, T., Chen, W. & Zeng, B.-B. (2011). Tetrahedron, 67, 6202-6205.  [Web of Science] [CrossRef] [ChemPort]
Inversen, L. F., Anderson, H. S., Branner, S., Moretensen, S. P., Peters, G. H., Norris, K., Olsen, O. H., Jeppesen, C. B., Lundt, B. F., Ripka, W., Moller, K. B. & Moller, N. P. H. (2000). J. Biol. Chem. 275, 10300-10307.  [PubMed]
Mabkhot, Y. N., Alatibi, F., Barakat, A., Choudhary, M. I. & Yousuf, S. (2013). Acta Cryst. E69, o1049.  [CrossRef] [IUCr Journals]
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Webb, T. R., Melman, N., Lvovskiy, D., Ji, X. & Jacobson, K. A. (2000). Bioorg. Med. Chem. Lett. 10, 31-34.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1244-o1245   [ doi:10.1107/S1600536813018734 ]

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