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Volume 69 
Part 8 
Page o1259  
August 2013  

Received 1 July 2013
Accepted 10 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.104
Data-to-parameter ratio = 20.6
Details
Open access

4-Phenyl-1,2,4-triazaspiro[4.5]dec-1-ene-3-thione

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C13H15N3S, the 4,5-dihydro-3H-1,2,4-triazole ring is nearly planar [maximum deviation = 0.020 (1) Å], while the cyclohexane ring adopts a chair conformation. The dihedral angle between the 4,5-dihydro-3H-1,2,4-triazole ring and the phenyl ring is 74.68 (7)°. No specific intermolecular interactions are discerned in the crystal packing.

Related literature

For wide-spectrum medicinal applications of spiro compounds incorporating heterocyclic substructures, see: Patil et al. (2010[Patil, B. S., Krishnamurthy, G., BhojyaNaik, H. S., Latthe, P. R. & Ghate, M. (2010). Eur. J. Med. Chem. 45, 3329-3334.]); Pawar et al. (2009[Pawar, M. J., Burungale, A. B. & Karale, B. K. (2009). ARKIVOC, XIII, 97-107.]); Thadhaney et al. (2010[Thadhaney, B., Sain, D., Pernawat, G. & Talesara, G. L. (2010). Indian J. Chem. Sect. B, 49, 368-373.]); Chin et al. (2008[Chin, Y.-W., Salim, A. A., Su, B.-N., Mi, Q., Chai, H.-B., Riswan, S., Kardono, L. B. S., Ruskandi, A., Farnsworth, N. R., Swanson, S. M. & Kinghorn, A. D. (2008). J. Nat. Prod. 3, 390-395.]); Wang et al. (2007[Wang, W.-L., Zhu, T.-J., Tao, H.-W., Lu, Z.-Y., Fang, Y.-C., Gu, Q.-Q. & Zhu, W.-M. (2007). Chem. Biodivers. 4, 2913-2919.]); Chande et al. (2005[Chande, M. S., Verma, R. S., Barve, P. A., Khanwelkar, R. R., Vaidya, R. B. & Ajaikumar, K. B. (2005). Eur. J. Med. Chem. 40, 1143-1148.]); Obniska et al. (2006[Obniska, J., Kaminski, K. & Tatarczynska, E. (2006). Pharmacol. Rep. 58, 207-214.]); Kaminski et al. (2008[Kaminski, K., Obniska, J. & Dybala, M. (2008). Eur. J. Med. Chem. 43, 53-61.]); Sarma et al. (2010[Sarma, B. K., Manna, D., Minoura, M. & Mugesh, G. (2010). J. Am. Chem. Soc. 132, 5364-5374.]); Shimakawa et al. (2003[Shimakawa, S., Yoshida, Y. & Niki, E. (2003). Lipids, 38, 225-231.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15N3S

  • Mr = 245.34

  • Orthorhombic, P b c a

  • a = 9.4952 (9) Å

  • b = 7.4845 (7) Å

  • c = 34.692 (3) Å

  • V = 2465.5 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 150 K

  • 0.28 × 0.22 × 0.17 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.810, Tmax = 0.960

  • 41202 measured reflections

  • 3168 independent reflections

  • 2899 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.104

  • S = 1.10

  • 3168 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: TK5237 ).


Acknowledgements

Tulane University, Erciyes University and Minia University are gratefully acknowledged for supporting this study.

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chande, M. S., Verma, R. S., Barve, P. A., Khanwelkar, R. R., Vaidya, R. B. & Ajaikumar, K. B. (2005). Eur. J. Med. Chem. 40, 1143-1148.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Chin, Y.-W., Salim, A. A., Su, B.-N., Mi, Q., Chai, H.-B., Riswan, S., Kardono, L. B. S., Ruskandi, A., Farnsworth, N. R., Swanson, S. M. & Kinghorn, A. D. (2008). J. Nat. Prod. 3, 390-395.  [Web of Science] [CrossRef]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Kaminski, K., Obniska, J. & Dybala, M. (2008). Eur. J. Med. Chem. 43, 53-61.  [Web of Science] [PubMed]
Obniska, J., Kaminski, K. & Tatarczynska, E. (2006). Pharmacol. Rep. 58, 207-214.  [PubMed] [ChemPort]
Patil, B. S., Krishnamurthy, G., BhojyaNaik, H. S., Latthe, P. R. & Ghate, M. (2010). Eur. J. Med. Chem. 45, 3329-3334.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Pawar, M. J., Burungale, A. B. & Karale, B. K. (2009). ARKIVOC, XIII, 97-107.  [CrossRef]
Sarma, B. K., Manna, D., Minoura, M. & Mugesh, G. (2010). J. Am. Chem. Soc. 132, 5364-5374.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shimakawa, S., Yoshida, Y. & Niki, E. (2003). Lipids, 38, 225-231.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thadhaney, B., Sain, D., Pernawat, G. & Talesara, G. L. (2010). Indian J. Chem. Sect. B, 49, 368-373.
Wang, W.-L., Zhu, T.-J., Tao, H.-W., Lu, Z.-Y., Fang, Y.-C., Gu, Q.-Q. & Zhu, W.-M. (2007). Chem. Biodivers. 4, 2913-2919.  [CSD] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1259  [ doi:10.1107/S1600536813019120 ]

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