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Volume 69 
Part 3 
Page o434  
March 2013  

Received 19 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.098
Data-to-parameter ratio = 16.0
Details
Open access

2-Methylsulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,cApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C10H8N4S2, comprising fused six-, six- and five-membered rings, the molecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041 Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {...HNCN}2 synthons in the crystal. The resulting inversion dimers are connected into supramolecular stacks aligned along the b-axis direction by [pi]-[pi] interactions [centroid-centroid distances = 3.6531 (12) and 3.7182 (12) Å].

Related literature

For background to the biological activity of triazoloquinazolines, see: Pierce et al. (2004[Pierce, A. C., Arnost, M., Davies, R. J., Forster, C. J., Galullo, V., Grey, R., Ledeboer, M., Tian, S.-K., Xu, J., Binch, H., Ledford, B., Messersmith, D., Nanthakumar, S. & Jayaraj, A. (2004). Chem. Abstr. 141, 23537.]); Al-Salahi & Geffken (2010[Al-Salahi, R. & Geffken, D. (2010). Molecules, 15, 7016-7034.], 2011[Al-Salahi, R. & Geffken, D. (2011). Synth. Commun. 41, 3512-3523.]); Al-Salahi et al. (2011[Al-Salahi, R., Geffken, D. & Koellner, M. (2011). Chem. Pharm. Bull. 59, 730-733.], 2013[Al-Salahi, R., Gamal-Eldeen, A. M., Alanazi, A. M., Al-Omar, M. A., Marzouk, M. A. & Fouda, M. M. G. (2013). Molecules, 18, 1434-1446.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N4S2

  • Mr = 248.32

  • Monoclinic, P 21 /c

  • a = 10.5414 (11) Å

  • b = 4.9335 (6) Å

  • c = 20.0943 (19) Å

  • [beta] = 99.127 (10)°

  • V = 1031.79 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 295 K

  • 0.30 × 0.15 × 0.05 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.864, Tmax = 1.000

  • 5096 measured reflections

  • 2389 independent reflections

  • 1667 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.098

  • S = 0.93

  • 2389 reflections

  • 149 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.28 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-H1...N4i 0.87 (1) 2.07 (1) 2.931 (2) 171 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: HB7045 ).


Acknowledgements

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al-Salahi, R., Gamal-Eldeen, A. M., Alanazi, A. M., Al-Omar, M. A., Marzouk, M. A. & Fouda, M. M. G. (2013). Molecules, 18, 1434-1446.  [ChemPort] [PubMed]
Al-Salahi, R. & Geffken, D. (2010). Molecules, 15, 7016-7034.  [ChemPort]
Al-Salahi, R. & Geffken, D. (2011). Synth. Commun. 41, 3512-3523.  [ChemPort]
Al-Salahi, R., Geffken, D. & Koellner, M. (2011). Chem. Pharm. Bull. 59, 730-733.  [ChemPort] [PubMed]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Pierce, A. C., Arnost, M., Davies, R. J., Forster, C. J., Galullo, V., Grey, R., Ledeboer, M., Tian, S.-K., Xu, J., Binch, H., Ledford, B., Messersmith, D., Nanthakumar, S. & Jayaraj, A. (2004). Chem. Abstr. 141, 23537.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o434  [ doi:10.1107/S1600536813004881 ]

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