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Volume 69 
Part 9 
Page o1407  
September 2013  

Received 5 August 2013
Accepted 5 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.108
Data-to-parameter ratio = 14.7
Details
Open access

3-Benzhydryl-1,3,4-thiadiazole-2(3H)-thione

aStrategic Research Centre for Biotechnology, Chemistry and Systems Biology, Deakin University, Vic 3216, Australia,bQueensland Micro and Nanotechnology Centre, Griffith University, Brisbane 4111, Australia, and cSchool of Chemistry, Physics & Mechanical Engineering, Queensland University of Technology, Brisbane 4001, Australia
Correspondence e-mail: P.Healy@griffith.edu.au

In the title compound, C15H12N2S2, the two phenyl rings and the planar (r.m.s. deviation = 0.002 Å) thiadiazole ring adopt a propeller conformation about the central C-H axis with H-C-C-C(phenyl) torsion angles of 44 and 42° and an H-C-N-C(thiadiazole) torsion angle of 28°. Intramolecular C-H...S and C-H...N contacts are observed. In the crystal, centrosymmetrically related molecules associate through C-H...[pi] interactions. These are connected into a supramolecular chain along [101] by C-H...N interactions.

Related literature

For details of the use of 1,3,4-thiadiazoles in the synthesis of crown ethers, see: Pappalardo et al. (1987[Pappalardo, S., Bottino, F. & Tringali, C. (1987). J. Org. Chem. 52, 3409-3413.]). For their uses as scaffolds in potential pharmaceuticals, see; Aggarwal et al. (2012[Aggarwal, N., Kumar, R., Dureja, P. & Khurana, J. M. (2012). Chem. Biol. Drug Des. 79, 384-397.]); Bhole & Bhusari (2011[Bhole, R. P. & Bhusari, K. P. (2011). Med. Chem. Res. 20, 695-704.]); Ghani & Ullah (2010[Ghani, U. & Ullah, N. (2010). Bioorg. Med. Chem. 18, 4042-4048.]); Kadi et al. (2010[Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006-5011.]); Zhan et al. (2009[Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2S2

  • Mr = 284.41

  • Monoclinic, P 21 /n

  • a = 9.1198 (4) Å

  • b = 15.4226 (5) Å

  • c = 10.7584 (4) Å

  • [beta] = 108.546 (5)°

  • V = 1434.60 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 223 K

  • 0.44 × 0.29 × 0.18 mm

Data collection
  • Oxford-Diffraction GEMINI S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.859, Tmax = 0.938

  • 5244 measured reflections

  • 2524 independent reflections

  • 2144 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.108

  • S = 1.13

  • 2524 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C21-C26 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C1-H1...S2 0.95 2.76 3.181 (2) 108
C16-H16...N3 0.95 2.58 2.897 (3) 100
C5-H5...Cg2i 0.95 2.74 3.670 (3) 157
C13-H13...N4ii 0.95 2.60 3.495 (3) 157
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001[Molecular Structure Corporation. (2001). TEXSAN for Windows. MSC, The Woodlands, Texas, USA.]) and SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: TEXSAN and 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.]); software used to prepare material for publication: 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: TK5245 ).


Acknowledgements

We acknowledge support of this work by the Micro and Nanotechnology Centre, Griffith University, the Central Analytical Research Facility, Queensland University of Technology, and the Strategic Research Centre for Biotechnology, Chemistry and Systems Biology, Deakin University.

References

Aggarwal, N., Kumar, R., Dureja, P. & Khurana, J. M. (2012). Chem. Biol. Drug Des. 79, 384-397.  [CrossRef] [ChemPort] [PubMed]
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bhole, R. P. & Bhusari, K. P. (2011). Med. Chem. Res. 20, 695-704.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ghani, U. & Ullah, N. (2010). Bioorg. Med. Chem. 18, 4042-4048.  [CrossRef] [ChemPort] [PubMed]
Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006-5011.  [ISI] [CrossRef] [ChemPort] [PubMed]
Molecular Structure Corporation. (2001). TEXSAN for Windows. MSC, The Woodlands, Texas, USA.
Pappalardo, S., Bottino, F. & Tringali, C. (1987). J. Org. Chem. 52, 3409-3413.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1407  [ doi:10.1107/S1600536813021867 ]

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