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Volume 69 
Part 5 
Page o684  
May 2013  

Received 2 April 2013
Accepted 5 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.047
wR = 0.123
Data-to-parameter ratio = 17.8
Details
Open access

3-[(4-Phenylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: Edward.Tiekink@gmail.com

In the title compound, C17H18N4OS2, the 2-thienyl ring is disordered over two co-planar, opposite orientations in a 0.684 (2): 0.316 ratio. The 1,3,4-oxadiazole ring is almost co-planar with the attached 2-thienyl ring [dihedral angles of 5.34 (19) and 4.8 (5)° for the major and minor components, respectively]. The relative disposition of the thione- and ring-S atoms is anti for the major orientation of the 2-thienyl residue. Overall, the shape of the molecule approximates the letter V. In the crystal, a three-dimensional architecture is consolidated by a combination of weak C-H...S and C-H...[pi] contacts.

Related literature

For background to the biological properties of 1,3,4-oxadiazole derivatives, see: Al-Omar (2010[Al-Omar, M. A. (2010). Molecules, 15, 502-514.]). For a related structure, see: El-Emam et al. (2012[El-Emam, A. A., Al-Omar, M. A., Ghabbour, H. A., Fun, H.-K. & Chia, T. S. (2012). Acta Cryst. E68, o1345-o1346.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18N4OS2

  • Mr = 358.47

  • Monoclinic, C 2/c

  • a = 26.1721 (17) Å

  • b = 5.7253 (3) Å

  • c = 23.7008 (18) Å

  • [beta] = 97.802 (6)°

  • V = 3518.5 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.887, Tmax = 1.000

  • 9546 measured reflections

  • 4083 independent reflections

  • 2797 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.123

  • S = 1.06

  • 4083 reflections

  • 230 parameters

  • 33 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the O1,N1,N2,C5,C6 ring

D-H...A D-H H...A D...A D-H...A
C9-H9B...S2i 0.97 2.77 3.618 (3) 146
C1-H1...Cg1ii 0.93 2.72 3.545 (6) 148
C11-H11A...Cg1iii 0.97 2.98 3.600 (2) 123
C15-H15...Cg2iii 0.93 2.95 3.743 (3) 144
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: HB7064 ).


Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/03).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Omar, M. A. (2010). Molecules, 15, 502-514.  [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Emam, A. A., Al-Omar, M. A., Ghabbour, H. A., Fun, H.-K. & Chia, T. S. (2012). Acta Cryst. E68, o1345-o1346.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o684  [ doi:10.1107/S1600536813009252 ]

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