(E)-2-(2,3-Dimethylanilino)-N′-(thiophen-2-ylmethylidene)benzohydrazide

Hoong-Kun Fun,Mohamed A Al-Omar,Hatem A Abdel-Aziz,Mashooq A Bhat,Tze Shyang Chia

doi:10.1107/s160053681203259x

Abstract

In the title compound, C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thiophene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thiophene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thiophene ring and the benzene ring are twisted from the mean plane of the C(=O)—N—N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C—H⋯π interactions.

Highlights

In the title compound, C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9) with the thiophene ring and the dimethyl-substituted benzene ring, respectively
The thiophene ring and the benzene ring are twisted from the mean plane of the C( O)—N—N C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9)
In view of the importance of the chemistry and biological activity of diaryl amines (Reddy et al, 2010) and in continuation to our interest in the chemistry of hydrazones (Bhat et al, 2012a,b,c), we report the crystal structure of the title compound

Summary

Crystal data

USM, Penang, Malaysia, and bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9) with the thiophene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thiophene ring and dimethyl-substituted benzene ring is 83.60 (9). The thiophene ring and the benzene ring are twisted from the mean plane of the C( O)—N—N C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9). An intramolecular N—H O hydrogen bond generates an S(6) ring. Molecules are linked by N—H O and C—H O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane.

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