2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazoleAdditional correspondence author, e-mail: bakrfatehy@yahoo.com.

Abdel-Wahab, B.F.; Mohamed, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681300384X

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 (C-C) = 0.005 Å
R = 0.048
wR = 0.172
Data-to-parameter ratio = 17.3
Details

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

Bakr F. Abdel-Wahab,^a Hanan A. Mohamed,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^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 C_m-O-C_b-C_b 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); Karki et al. (2011); Khazi et al. (2011). For the synthesis, see: Abdel-Wahab et al. (2011). For a related structure, see: Fun et al. (2011).

Experimental

Crystal data

C₁₈H₁₃Cl₂N₃OS
M_r = 390.27
Triclinic, $[P \overline 1]$
a = 8.3015 (7) Å
b = 8.3053 (7) Å
c = 14.4374 (13) Å
= 97.180 (7)°
= 92.644 (7)°
= 118.996 (9)°
V = 857.25 (13) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.856, T_max = 1.000
8391 measured reflections
3932 independent reflections
2659 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.172
S = 0.98
3932 reflections
227 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
Fun, H.-K., Hemamalini, M., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011). Acta Cryst. E67, o254.
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, I. A. M., Gadad, A. K., Lamani, R. S. & Bhongade, B. A. (2011). Tetrahedron, 67, 3289-3316.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.