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

Bakr F Abdel-Wahab,Edward R T Tiekink,Seik Weng Ng,Hanan A Mohamed

doi:10.1107/s160053681300384x

Abstract

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 π–π 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].

Highlights

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—
Supramolecular tapes along the b axis are found in the crystal structure which are mediated by – 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]

Summary

Data collection

Egypt, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz. R factor = 0.048; wR factor = 0.172; data-to-parameter ratio = 17.3. 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 – 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]

Agilent SuperNova Dual diffractometer with an Atlas detector

Special details