5-[1-(3,4-Dichloro-phen-oxy)eth-yl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate.

Tashfeen Akhtar,Shahid Hameed,M Khawar Rauf,Xiaoming Lu

doi:10.1107/s1600536809029894

Tashfeen Akhtar, Shahid Hameed + Show 2 more

Open Access

https://doi.org/10.1107/s1600536809029894

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Abstract

In the title compound, C10H8Cl2N2O2S·0.5H2O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds involving the water molecule, which is situated on an a twofold rotation axis, and two organic molecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp3 hybridization. The dihedral angle between the mean plane of the benzene ring of the dichlorophenyl group and the mean plane of the oxadiazole ring is 74.18 (4)°. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯S hydrogen bonds.

Highlights

In the title compound, C10H8Cl2N2O2S0.5H2O, the atoms in the oxadiazole ring are essentially coplanar
H atoms treated by a mixture of independent and constrained refinement max = 0.22 e Å3
N—H O hydrogen bonds involving the water molecule, which is situated on an a twofold rotation axis, and two organic molecules, leading to a thione tautomer in the solid state

Summary

Data collection

Rint = 0.019 a Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bDepartment of Chemistry, Capital Normal University, Beijing Taiyuan 100037, People’s Republic of China. H atoms treated by a mixture of independent and constrained refinement max = 0.22 e Å3. C10H8Cl2N2O2S0.5H2O, the atoms in the oxadiazole ring are essentially coplanar N—H O hydrogen bonds involving the water molecule, which is situated on an a twofold rotation axis, and two organic molecules, leading to a thione tautomer in the solid state. The. C atom attached to the oxadiazole ring adopts a typical sp hybridization. The dihedral angle between the mean plane of the benzene ring of the dichlorophenyl group and the mean plane of the oxadiazole ring is 74.18 (4). The crystal structure is stabilized by intermolecular N—H O and O—H S hydrogen bonds

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