(E)-2-[1-(1-Benzothio-phen-2-yl)ethyl-idene]-N-phenyl-hydrazinecarboxamide.

Ibrahim Baba,Safa'a Faris Kayed,Jim Simpson,Yang Farina

doi:10.1107/s1600536811037457

Abstract

The title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit. The two molecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both molecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothiophene groups and N-bound phenyl rings are 36.36 (9)° for molecule 1 and 29.71 (9)° for molecule 2. The C=N—NH—C(O)NH ethylidene–hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two molecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in molecules 1 and 2. This conformation is enhanced by weak intramolecular C—H⋯O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each molecule. In the crystal, pairs of molecules are linked by pairs of intermolecular N—H⋯O hydrogen bonds into dimers. Alternating dimers are further interconnected by weak C—H⋯O contacts into zigzag rows along b. The rows are stacked along a by C—H⋯π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothiophene units.

Highlights

The title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit
The dihedral angles between the benzothiophene groups and N-bound phenyl rings are
The C N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11), respectively, in molecules 1 and 2

Summary

Structure Reports

Safa’a Faris Kayed,a* Yang Farina,a Jim Simpsonb and Ibrahim Babaa a School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM, Bangi, Selangor, Malaysia, and bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin. Both molecules adopt E configurations with respect to the C N bonds. The C N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11) , respectively, in molecules 1 and 2. This conformation is enhanced by weak intramolecular C—H O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each molecule. Pairs of molecules are linked by pairs of intermolecular N—H O hydrogen bonds into dimers. The rows are stacked along a by C—H contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothiophene units

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