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Volume 69 
Part 10 
Pages o1563-o1564  
October 2013  

Received 11 September 2013
Accepted 13 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 20.1
Details
Open access

(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole

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

In the title compound, C24H20BrN3S, the dihydrothiazole ring is approximately planar, with a maximum deviation of 0.008 (2) Å, and is twisted with respect to the 4-bromophenyl ring, the phenyl ring and methylphenyl ring, making dihedral angles of 47.96 (8), 59.52 (9) and 16.96 (9)°, respectively. In the crystal, weak C-H...[pi] interactions link inversion-related molecules into supramolecular dimers.

Related literature

For the syntheses of similar thiazolidine compounds, see, for example: Masoudi et al. (2010[Masoudi, M., Darehkordi, A. & Moshrefi, A. (2010). World Appl. Sci. J. 10, 1313-1320.]); Darehkordia et al. (2007[Darehkordia, A., Kazem Saidib, K. & Islami, M. R. (2007). ARKIVOC, i 180-188.]) and for the synthesis of a related compound, see: Mohamed et al. (2013[Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1324.]). For the range of biological activities of thiazolidine-containing compounds, see: Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClerq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.]); 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., Mokale, V. & Raut, M. (2007). Bioorg. Med. Chem. 15, 3997-4008.]); Gududuru et al. (2004[Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.]); Taranalli et al. (2009[Taranalli, A. D., Thimmaiah, N. V., Srinivas, S. & Saravanan, E. (2009). Asia. J. Pharm. Clin. Res. 2, 79-83.]); Kumar et al. (2007[Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.]); Rao et al. (2002[Rao, A., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Christophe Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 747-751.], 2004[Rao, A., Balzarini, J., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappalá, M. (2004). Il Farmaco, 59, 33-39.]); Barreca et al. (2001[Barreca, M. L., Chimirri, A., De Luca, L., Monforte, A. M., Monforte, P. A., Rao, A., Zappalà, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M. (2001). Bioorg. Med. Chem. Lett. 11, 1793-1796.]); Solomon et al. (2007[Solomon, V. R., Haq, W., Srivastava, K., Puri, S. K. & Katti, S. B. (2007). J. Med. Chem. 50, 394-398.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20BrN3S

  • Mr = 462.40

  • Triclinic, [P \overline 1]

  • a = 7.9622 (5) Å

  • b = 11.2672 (7) Å

  • c = 11.6370 (7) Å

  • [alpha] = 96.273 (1)°

  • [beta] = 94.386 (1)°

  • [gamma] = 96.302 (1)°

  • V = 1027.31 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.12 mm-1

  • T = 150 K

  • 0.23 × 0.17 × 0.14 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 = 0.60, Tmax = 0.76

  • 18958 measured reflections

  • 5310 independent reflections

  • 4582 reflections with i > 2[sigma](i)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.09

  • 5310 reflections

  • 264 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.97 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18-C23 benzene ring.

D-H...A D-H H...A D...A D-H...A
C17-H17A...Cg4i 0.98 2.77 3.595 (3) 143
Symmetry code: (i) -x+3, -y, -z+2.

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.]); 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: XU5739 ).


Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University 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]
Barreca, M. L., Chimirri, A., De Luca, L., Monforte, A. M., Monforte, P. A., Rao, A., Zappalà, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M. (2001). Bioorg. Med. Chem. Lett. 11, 1793-1796.  [CrossRef] [PubMed] [ChemPort]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Darehkordia, A., Kazem Saidib, K. & Islami, M. R. (2007). ARKIVOC, i 180-188.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.  [CrossRef] [PubMed] [ChemPort]
Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.  [CrossRef] [PubMed] [ChemPort]
Masoudi, M., Darehkordi, A. & Moshrefi, A. (2010). World Appl. Sci. J. 10, 1313-1320.  [ChemPort]
Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1324.  [CSD] [CrossRef] [IUCr Journals]
Pandeya, S. N., Sriram, D., Nath, G. & DeClerq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rao, A., Balzarini, J., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappalá, M. (2004). Il Farmaco, 59, 33-39.  [CrossRef] [PubMed] [ChemPort]
Rao, A., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Christophe Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 747-751.  [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.  [CSD] [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., Mokale, V. & Raut, M. (2007). Bioorg. Med. Chem. 15, 3997-4008.  [CrossRef] [PubMed] [ChemPort]
Solomon, V. R., Haq, W., Srivastava, K., Puri, S. K. & Katti, S. B. (2007). J. Med. Chem. 50, 394-398.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Taranalli, A. D., Thimmaiah, N. V., Srinivas, S. & Saravanan, E. (2009). Asia. J. Pharm. Clin. Res. 2, 79-83.  [ChemPort]


Acta Cryst (2013). E69, o1563-o1564   [ doi:10.1107/S1600536813025506 ]

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