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Volume 68 
Part 5 
Pages o1345-o1346  
May 2012  

Received 28 March 2012
Accepted 3 April 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.048
wR = 0.156
Data-to-parameter ratio = 12.2
Details
Open access

3-[(N-Methylanilino)methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C14H13N3OS2, the thiophene ring is disordered over two orientations by ca 180° about the C-C bond axis linking the ring to the rest of the molecule, with a site-occupancy ratio of 0.651 (5):0.349 (5). The central 1,3,4-oxadiazole-2(3H)-thione ring forms dihedral angles of 9.2 (5), 4.6 (11) and 47.70 (7)° with the major and minor parts of the disordered thiophene ring and the terminal phenyl ring, respectively. In the crystal, no significant intermolecular hydrogen bonds are observed. The crystal packing is stabilized by [pi]-[pi] interactions [centroid-centroid distance = 3.589 (2) Å].

Related literature

For the biological activity of 1,3,4-oxadiazole derivatives, see: Navarrete-Vázquez et al. (2007[Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S. & Gonzàlez-Salazar, F. (2007). Bioorg. Med. Chem. 15, 5502-5508.]); Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]); Padmavathi et al. (2009[Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106-2112.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]); Al-Deeb et al. (2006[Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.]). For the synthesis of the title compound, see: Al-Omar (2010[Al-Omar, M. A. (2010). Molecules, 15, 502-514.]). For related 1,3,4-oxadiazole structures, see: Fun et al. (2011[Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372.]); El-Emam et al. (2012[El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3OS2

  • Mr = 303.39

  • Monoclinic, P 21 /n

  • a = 11.9682 (8) Å

  • b = 7.4526 (5) Å

  • c = 17.0749 (14) Å

  • [beta] = 108.072 (6)°

  • V = 1447.85 (18) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.32 mm-1

  • T = 296 K

  • 0.92 × 0.16 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.150, Tmax = 0.754

  • 10021 measured reflections

  • 2676 independent reflections

  • 1516 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.156

  • S = 0.97

  • 2676 reflections

  • 220 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS5107 ).


Acknowledgements

AAEE, MAAO and HAG thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for financial support. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship.

References

Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug. Res. 56, 40-47.  [ChemPort]
Al-Omar, M. A. (2010). Molecules, 15, 502-514.  [ChemPort] [PubMed]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.  [CrossRef] [PubMed] [ChemPort]
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795.  [CSD] [CrossRef] [details]
Fun, H.-K., Arshad, S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3372.  [CSD] [CrossRef] [details]
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.  [ISI] [CrossRef] [PubMed] [ChemPort]
Navarrete-Vázquez, G., Molina-Salinas, G. M., Duarte-Fajardo, Z. V., Vargas-Villarreal, J., Estrada-Soto, S. & Gonzàlez-Salazar, F. (2007). Bioorg. Med. Chem. 15, 5502-5508.  [PubMed]
Padmavathi, V., Reddy, G. S., Padmaja, A., Kondaiah, P. & Shazia, A. (2009). Eur. J. Med. Chem. 44, 2106-2112.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o1345-o1346   [ doi:10.1107/S1600536812014419 ]

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