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Volume 69 
Part 8 
Page o1324  
August 2013  

Received 19 July 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.119
Data-to-parameter ratio = 19.1
Details
Open access

(1Z,2E)-1-(3,4-Diphenyl-2,3-dihydro-1,3-thiazol-2-ylidene)-2-(1-p-tolylethylidene)hydrazine

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

In the title compound, C24H21N3S, the thiazole ring makes dihedral angles of 52.03 (6), 62.63 (6) and 12.35 (6)°, respectively, with the two phenyl rings and the benzene ring. In the crystal, weak C-H...[pi] interactions occur between inversion-related molecules.

Related literature

For the syntheses and bioactivity of thiazole-containing compounds, see: Siddiqui et al. (2009[Siddiqui, N., Arshad, M. F., Ahsan, W. & Alam, M. S. (2009). IJPSDR, 1, 136-143.]); Ramla et al. (2006[Ramla, M. M., Omar, M. A., El-Khamry, A. M. M. & El-Diwan, H. I. (2006). Bioorg. Med. Chem. 14, 7324-7332.]); Popsavin et al. (2007[Popsavin, M., Spaic, S., Svircev, M., Kojic, V., Bogdanovic, G. & Popsavin, V. (2007). Bioorg. Med. Chem. Lett. 17, 4123-4127.]); Kumar et al. (2007[Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClerq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.]); Narayana et al. (2004[Narayana, B., Raj, K. K. V., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2004). Eur. J. Med. Chem. 39, 867-872.]); Shiradkar et al. (2007[Shiradkar, M. R., Murahari, K. K., Gangadasu, H. R., Suresh, T., Kalyan, C. A., Panchal, D., Kaur, R., Burange, P., Ghogare, J., Mokalec, V. & Raut, M. (2007). Bioorg. Med. Chem. 15, 3997-4008.]); Amin et al. (2008[Amin, K. M., Rahman, A. D. E. & Al-Eryani, Y. A. (2008). Bioorg. Med. Chem. 16, 5377-5388.]); Shih & Ying (2004[Shih, M. H. & Ying, K. F. (2004). Bioorg. Med. Chem. 12, 4633-4643.]); Andreani et al. (1987[Andreani, A., Rambaldi, M., Mascellani, G. & Rugarli, P. (1987). Eur. J. Med. Chem. 22, 19-22.]).

[Scheme 1]

Experimental

Crystal data
  • C24H21N3S

  • Mr = 383.51

  • Triclinic, [P \overline 1]

  • a = 7.9370 (8) Å

  • b = 10.7587 (11) Å

  • c = 11.9325 (13) Å

  • [alpha] = 94.922 (2)°

  • [beta] = 97.436 (2)°

  • [gamma] = 95.383 (2)°

  • V = 1000.95 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 150 K

  • 0.30 × 0.15 × 0.12 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 = 0.83, Tmax = 0.98

  • 17908 measured reflections

  • 4870 independent reflections

  • 4287 reflections with I > 2[sigma](I)

  • Rint = 0.034

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

  • wR(F2) = 0.119

  • S = 1.06

  • 4870 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18-C23 ring.

D-H...A D-H H...A D...A D-H...A
C15-H15...Cg4i 0.95 2.71 3.6170 (16) 160
C16-H16A...Cg4ii 0.98 2.77 3.5984 (16) 143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: XU5722 ).


Acknowledgements

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

References

Amin, K. M., Rahman, A. D. E. & Al-Eryani, Y. A. (2008). Bioorg. Med. Chem. 16, 5377-5388.  [CrossRef] [PubMed] [ChemPort]
Andreani, A., Rambaldi, M., Mascellani, G. & Rugarli, P. (1987). Eur. J. Med. Chem. 22, 19-22.  [CrossRef] [ChemPort]
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.  [CrossRef] [PubMed] [ChemPort]
Narayana, B., Raj, K. K. V., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2004). Eur. J. Med. Chem. 39, 867-872.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Pandeya, S. N., Sriram, D., Nath, G. & DeClerq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.  [CrossRef] [PubMed] [ChemPort]
Popsavin, M., Spaic, S., Svircev, M., Kojic, V., Bogdanovic, G. & Popsavin, V. (2007). Bioorg. Med. Chem. Lett. 17, 4123-4127.  [CrossRef] [PubMed] [ChemPort]
Ramla, M. M., Omar, M. A., El-Khamry, A. M. M. & El-Diwan, H. I. (2006). Bioorg. Med. Chem. 14, 7324-7332.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shih, M. H. & Ying, K. F. (2004). Bioorg. Med. Chem. 12, 4633-4643.  [CrossRef] [PubMed] [ChemPort]
Shiradkar, M. R., Murahari, K. K., Gangadasu, H. R., Suresh, T., Kalyan, C. A., Panchal, D., Kaur, R., Burange, P., Ghogare, J., Mokalec, V. & Raut, M. (2007). Bioorg. Med. Chem. 15, 3997-4008.  [CrossRef] [PubMed] [ChemPort]
Siddiqui, N., Arshad, M. F., Ahsan, W. & Alam, M. S. (2009). IJPSDR, 1, 136-143.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1324  [ doi:10.1107/S1600536813020254 ]

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