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

Al-Adiwish, W.M.; Adan, D.; Mohamed Tahir, M.I.; Yaacob, W.A.; Kassim, M.B.

doi:10.1107/S1600536811052950

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 15.0
Details

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

Wedad M. Al-Adiwish,^a D. Adan,^a Mohamed Ibrahim Mohamed Tahir,^b W.A. Yaacob ^a and Mohammad B. Kassim ^a,^c ^*

^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-HN 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). For related structures, see: El-Saghier (2002); Eller & Holzer (2006); Thomae et al. (2009); Al-Adiwish et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₂N₄S
M_r = 232.31
Monoclinic, C 2/c
a = 14.1637 (3) Å
b = 11.2823 (3) Å
c = 14.4413 (3) Å
= 98.131 (2)°
V = 2284.51 (9) Å³
Z = 8
Cu K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ) T_min = 0.679, T_max = 0.784
11636 measured reflections
2188 independent reflections
2026 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.098
S = 1.05
2188 reflections
146 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN3ⁱ	0.86	2.22	3.0576 (19)	164
N1-H1BN2ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
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
El-Saghier, A. M. M. (2002). Molecules 7, 756-766.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thomae, D., Perspicace, E., Henryon, D., Xu, Z. & Schneider, S. (2009). Tetrahedron, 65, 10453-10458.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds