Crystal structure and Hirshfeld surface analysis of rac-2-[2-(4-chloro-phen-yl)-3,4-di-hydro-2H-1-benzo-pyran-4-yl-idene]hydrazine-1-carbo-thio-amide.

Ruokuosenuo Zatsu,M Indira Devi,Prabhakar Maddela,Chullikkattil P Pradeep,Ranjit Singh

doi:10.1107/s2056989019005073

Abstract

In the title compound, C16H14N3OSCl, a Schiff base derivative of a thio-semicarbazide with a flavanone, the 4-chlorophenyl ring is inclined to the benzene ring of the chromane ring system by 30.72 (12)°. The pyran ring has an envelope conformation with the methine C atom as the flap. The mean plane of the thio-urea unit is twisted with respect to the benzene ring of the chromanone ring system, subtending a dihedral angle of 19.78 (19)°. In the crystal, mol-ecules are linked by two pairs of N-H⋯S hydrogen bonds, forming inversion dimers enclosing R 2 2(8) ring motifs, which are linked to form ribbons propagating along the b-axis direction. The inter-molecular contacts in the crystal have been analysed using Hirshfeld surface analysis.

Highlights

C16H14N3OSCl, a Schiff base derivative of a thiosemicarbazide with a flavanone, the 4-chlorophenyl ring is inclined to the benzene ring of the chromane ring system by 30.72 (12)
The mean plane of the thiourea unit is twisted with respect to the benzene ring of the chromanone ring system, subtending a dihedral angle of 19.78 (19)
Molecules are linked by two pairs of N—HÁ Á ÁS hydrogen bonds, forming inversion dimers enclosing R22(8) ring motifs, which are linked to form ribbons propagating along the b-axis direction

Summary

Chemical context

Flavanones, a subclass of flavonoids, are widely recognized for their nutraceutical values (Testai & Calderone, 2017). Schiff base derivatives of thiosemicarbazides have been studied for their biological and pharmacological properties (Bai et al, 2017). Schiff base derivatives of flavanones with thiosemicarbazides have not been explored extensively (Brodowska et al, 2016; Bargujar et al, 2018). The presence of NH and S moieties in such compounds opens up the possibility of studying the role of the comparatively less explored class of N—HÁ Á ÁS interactions in building supramolecular architectures. This is of interest as hydrogen bonding to sulfur is known to play an important role in biological systems (Andersen et al, 2014; Walters et al, 2005). There are no other significant short intermolecular interactions present

Structural commentary

Supramolecular features

Database survey

Findings

Synthesis and crystallization