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Volume 69 
Part 5 
Page o697  
May 2013  

Received 8 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.109
Data-to-parameter ratio = 17.6
Details
Open access

4-Benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-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, C13H11N3S2, the triazole and thiophene rings are coplanar [dihedral angle = 6.22 (13)°]. By contrast, the phenyl ring is perpendicular to the triazole ring [dihedral angle = 85.58 (13)°], so that the molecule has an L-shape. The thiophene S atom is syn with the ring imine N atom. In the crystal, eight-membered {...HNCS}2 synthons form between centrosymmetrically related molecules, leading to dimeric aggregates that are connected into a supramolecular layer parallel to (101) by [pi]-[pi] interactions between centrosymmetrically related triazole rings [centroid-centroid distance = 3.6091 (15) Å] and C-H...[pi] interactions.

Related literature

For the pharmacological properties (anti-inflammatory, anti-microbial and anti-cancer) of 1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991[El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260-1264.]); Navidpour et al. (2006[Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.]); Kumar et al. (2010[Kumar, G. V. S., Rajendraprasad, Y., Mallikarjuna, B. P., Chandrashekar, S. M. & Kistayya, C. (2010). Eur. J. Med. Chem. 45, 2063-2074.]); Wang et al. (2011[Wang, L., Tseng, W., Wu, T., Kaneko, K., Takayama, H., Kimura, M., Yange, W., Wu, J. B., Juang, S. & Wong, F. F. (2011). Bioorg. Med. Chem. Lett. 21, 5358-5362.]). For a related structure, see: Zareef et al. (2008[Zareef, M., Iqbal, R. & Parvez, M. (2008). Acta Cryst. E64, o952-o953.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3S2

  • Mr = 273.37

  • Monoclinic, P 21 /n

  • a = 13.422 (2) Å

  • b = 6.1670 (7) Å

  • c = 16.596 (2) Å

  • [beta] = 111.972 (15)°

  • V = 1273.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.40 mm-1

  • T = 295 K

  • 0.30 × 0.05 × 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 = 0.806, Tmax = 1.000

  • 6460 measured reflections

  • 2937 independent reflections

  • 2088 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.02

  • 2937 reflections

  • 167 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
N2-H2...S2i 0.88 (1) 2.43 (1) 3.297 (2) 169 (2)
C13-H13...Cg1ii 0.93 2.94 3.636 (3) 133
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\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: HG5308 ).


Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, 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.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260-1264.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kumar, G. V. S., Rajendraprasad, Y., Mallikarjuna, B. P., Chandrashekar, S. M. & Kistayya, C. (2010). Eur. J. Med. Chem. 45, 2063-2074.  [PubMed]
Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, L., Tseng, W., Wu, T., Kaneko, K., Takayama, H., Kimura, M., Yange, W., Wu, J. B., Juang, S. & Wong, F. F. (2011). Bioorg. Med. Chem. Lett. 21, 5358-5362.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zareef, M., Iqbal, R. & Parvez, M. (2008). Acta Cryst. E64, o952-o953.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o697  [ doi:10.1107/S1600536813009501 ]

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