Abstract
The title thio-urea derivative, C17H19N3OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the Ci-Ce-Ce-Cb torsion angle being -78.12 (18)°; i = imine, e = ethane and b = benzene. The configuration about the imine bond is E, the N-bound H atoms lie on opposite sides of the mol-ecule and an intra-molecular amine-N-H⋯N(imine) hydrogen bond is evident. In the mol-ecular packing, hydroxyl-O-H⋯S(thione) and amine-N-H⋯O hydrogen bonding feature within a linear, supra-molecular chain. The chains are connected into a layer in the ab plane by a combination of methyl-ene-C-H⋯S(thione), methyl-ene-C-H⋯O(hydrox-yl), methyl-C-H⋯π(phen-yl) and phenyl-C-H⋯π(hy-droxy-benzene) inter-actions. The layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface highlights the presence of weak methyl-C-H⋯O(hydrox-yl) and H⋯H inter-actions in the inter-layer region. Computational chemistry indicates that dispersion energy is the major contributor to the overall stabilization of the mol-ecular packing.
Highlights
The N-bound H atoms lie to opposite sides of the molecule, a conformation that allows for the formation of an intramolecular amine-N—HÁ Á ÁN(imine) hydrogen bond, Table 1
These chains arise because the hydroxyl-O—H atom forms a hydrogen bond to the thione-S1 atom and the hydroxyl-O1 atom simultaneously accepts a N—HÁ Á ÁO hydrogen bond from the amine-N2—H atom, Fig. 2(a)
They are connected into a supramolecular layer parallel to the c axis via methylene-C— HÁ Á ÁS(thione) and methylene-C—HÁ Á ÁO(hydroxyl) interactions as well as methyl-C—HÁ Á Á(phenyl) and phenyl-C— HÁ Á Á(hydroxybenzene) contacts, Table 1 and Fig. 2(b)
Summary
Known as 4-(4-hydroxyphenyl)-2butanone (C10H12O2), is a natural phenolic compound found in raspberries, kiwi fruit, brewed coffee, yew and orchid flowers (Lee, 2016). Raspberry ketone was condensed with 4-phenyl-3-thiosemicarbazide to form the title thiourea derivative, C17H19N3OS, hereafter designated as (I) Such compounds are of much interest due to their attractive and widespread pharmacological activities including anti-bacterial, anti-fungal, anti-tubercular, anticonvulsant, anti-tumour, anti-oxidant, anti-malarial and antihelmintic properties (Dincel & Guzeldemirci, 2020). While the N1-bound phenyl ring is approximately co-planar with the central residue, forming a dihedral angle of 7.94 (8), the terminal 4-hydroxybenzene ring is not, forming a dihedral angle of 67.00 (4); the dihedral angle between the rings is 73.64 (5) This conformation arises as there is a twist about the ethane bond, i.e. the C8—C10—C11—C12 torsion angle is À78.12 (18). The N-bound H atoms lie to opposite sides of the molecule, a conformation that allows for the formation of an intramolecular amine-N—HÁ Á ÁN(imine) hydrogen bond, Table 1
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
