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Volume 69 
Part 3 
Page o377  
March 2013  

Received 8 February 2013
Accepted 8 February 2013
Online 13 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.172
Data-to-parameter ratio = 17.3
Details
Open access

2-(2,4-Dichlorophenoxymethyl)-5-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole1

aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,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, C18H13Cl2N3OS, the eight atoms comprising the central imidazo/thiadiazolethiadiazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichlorobenzene and tolyl rings reflects a twist about the O-C(benzene) bond; the Cm-O-Cb-Cb torsion angle = -168.5 (2)° (m = methylene C and b is benzene C). Supramolecular tapes along the b axis are found in the crystal structure which are mediated by [pi]-[pi] interactions occurring between centrosymmetrically related thiadiazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].

Related literature

For background to the biological activity of imidazothiadiazoles, see: Abdel-Wahab et al. (2011[Abdel-Wahab, B. F., Farghaly, M. & Badria, F. A. (2011). Pharm. Chem. J. 45, 30-35.]); Karki et al. (2011[Karki, S. S., Panjamurthy, K., Kumar, S., Nambiar, M., Ramareddy, S. A., Chiruvella, K. K. & Raghavan, S. C. (2011). Eur. J. Med. Chem. 46, 2109-2116.]); Khazi et al. (2011[Khazi, I. A. M., Gadad, A. K., Lamani, R. S. & Bhongade, B. A. (2011). Tetrahedron, 67, 3289-3316.]). For the synthesis, see: Abdel-Wahab et al. (2011[Abdel-Wahab, B. F., Farghaly, M. & Badria, F. A. (2011). Pharm. Chem. J. 45, 30-35.]). For a related structure, see: Fun et al. (2011[Fun, H.-K., Hemamalini, M., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011). Acta Cryst. E67, o254.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13Cl2N3OS

  • Mr = 390.27

  • Triclinic, [P \overline 1]

  • a = 8.3015 (7) Å

  • b = 8.3053 (7) Å

  • c = 14.4374 (13) Å

  • [alpha] = 97.180 (7)°

  • [beta] = 92.644 (7)°

  • [gamma] = 118.996 (9)°

  • V = 857.25 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.51 mm-1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 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 = 0.856, Tmax = 1.000

  • 8391 measured reflections

  • 3932 independent reflections

  • 2659 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.172

  • S = 0.98

  • 3932 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

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: HG5290 ).


Acknowledgements

We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Abdel-Wahab, B. F., Farghaly, M. & Badria, F. A. (2011). Pharm. Chem. J. 45, 30-35.  [ChemPort]
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Hemamalini, M., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011). Acta Cryst. E67, o254.  [CSD] [CrossRef] [details]
Karki, S. S., Panjamurthy, K., Kumar, S., Nambiar, M., Ramareddy, S. A., Chiruvella, K. K. & Raghavan, S. C. (2011). Eur. J. Med. Chem. 46, 2109-2116.  [ISI] [CrossRef] [ChemPort] [PubMed]
Khazi, I. A. M., Gadad, A. K., Lamani, R. S. & Bhongade, B. A. (2011). Tetrahedron, 67, 3289-3316.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o377  [ doi:10.1107/S160053681300384X ]

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