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Volume 68 
Part 1 
Page o138  
January 2012  

Received 7 December 2011
Accepted 8 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 423 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 15.0
Details
Open access

3-Amino-5-(piperidin-1-yl)thiophene-2,4-dicarbonitrile

aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia,bDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia, and cFuel Cell Institute, Universiti Kebangsaan Malaysia, 43600 Selangor, Malaysia
Correspondence e-mail: mbkassim@ukm.my

In the title compound, C11H12N4S, the thiophene ring is roughly planar, with a maximum deviation of 0.012 (1) Å for the S atom, and makes a dihedral angle of 7.89 (8)° with the mean plane of the piperidine ring, which is in a chair conformation. The crystal packing is stabilized by pairs of centrosymmetric intermolecular N-H...N hydrogen bonds, which results in the formation of a step-wise chain parallel to [10[\overline1]].

Related literature

For the biological activity of aminothiophene derivatives, see: Abdel-Fattah et al. (2006[Abdel-Fattah, B., Kandeel, M. M., Abdel-Hakeem, M. & Fahmy, Z. M. (2006). J. Chin. Chem. Soc. 53, 3281-3291.]). For related structures, see: El-Saghier (2002[El-Saghier, A. M. M. (2002). Molecules 7, 756-766.]); Eller & Holzer (2006[Eller, G. A. & Holzer, W. (2006). Molecules, 11, 371-376]); Thomae et al. (2009[Thomae, D., Perspicace, E., Henryon, D., Xu, Z. & Schneider, S. (2009). Tetrahedron, 65, 10453-10458.]); Al-Adiwish et al. (2011[Al-Adiwish, W. M., Yaacob, W. A., Adan, D., Mohamed Tahir, M. I. & Kassim, M. B. (2011). Acta Cryst. E67, o3318.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N4S

  • Mr = 232.31

  • Monoclinic, C 2/c

  • a = 14.1637 (3) Å

  • b = 11.2823 (3) Å

  • c = 14.4413 (3) Å

  • [beta] = 98.131 (2)°

  • V = 2284.51 (9) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 2.33 mm-1

  • T = 423 K

  • 0.18 × 0.14 × 0.11 mm

Data collection
  • Oxford Diffraction Gemini CCD area-detector' diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]) Tmin = 0.679, Tmax = 0.784

  • 11636 measured reflections

  • 2188 independent reflections

  • 2026 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.098

  • S = 1.05

  • 2188 reflections

  • 146 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N3i 0.86 2.22 3.0576 (19) 164
N1-H1B...N2ii 0.86 2.29 3.0293 (17) 145
Symmetry codes: (i) [-x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x, y, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]); 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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2376 ).


Acknowledgements

The authors thank University Kebangsaan Malaysia for providing facilities and the Ministry of Science, Technology and Innovation for the research fund No. UKM-GGPM-KPB-098-2010. A PhD scholarship from the Libyan Government for WMA is greatly appreciated.

References

Abdel-Fattah, B., Kandeel, M. M., Abdel-Hakeem, M. & Fahmy, Z. M. (2006). J. Chin. Chem. Soc. 53, 3281-3291.
Al-Adiwish, W. M., Yaacob, W. A., Adan, D., Mohamed Tahir, M. I. & Kassim, M. B. (2011). Acta Cryst. E67, o3318.  [CrossRef] [details]
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.
Eller, G. A. & Holzer, W. (2006). Molecules, 11, 371-376  [CrossRef] [PubMed] [ChemPort]
El-Saghier, A. M. M. (2002). Molecules 7, 756-766.  [ChemPort]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thomae, D., Perspicace, E., Henryon, D., Xu, Z. & Schneider, S. (2009). Tetrahedron, 65, 10453-10458.  [ISI] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o138  [ doi:10.1107/S1600536811052950 ]

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