Crystal structure and Hirshfeld surface analysis of 2-{[7-acetyl-4-cyano-6-hy-droxy-8-(4-meth-oxyphen-yl)-1,6-dimethyl-5,6,7,8-tetra-hydro-isoquinolin-3-yl-]sulfan-yl}acetic acid ethyl ester.

Elham A Al-Taifi,Etify A Bakhite,Shaaban K Mohamed,Yasser A El-Ossaily,Joel T Mague,Mehmet Akkurt,Islam S Marae

doi:10.1107/s2056989022000378

Abstract

In the title mol-ecule, C25H28N2O5S, (alternative name ethyl 2-{[7-acetyl-4-cyano-6-hy-droxy-8-(4-meth-oxy-phen-yl)-1,6-dimethyl-5,6,7,8-tetra-hydro-isoquinolin-3-yl]sulfanyl}-acetate) the 4-meth-oxy-phenyl group is disposed on one side of the bicyclic core and the oxygen atoms of the hydroxyl and acetyl groups are disposed on the other side. In the crystal, a layered structure parallel to the ac plane is generated by O-H⋯O and C-H⋯O hydrogen bonds plus C-H⋯π(ring) inter-actions.

Highlights

C25H28N2O5S, (alternative name ethyl 2-{[7-acetyl-4-cyano6-hydroxy-8-(4-methoxyphenyl)-1,6-dimethyl-5,6,7,8-tetrahydroisoquinolin-3yl]sulfanyl}acetate) the 4-methoxyphenyl group is disposed on one side of the bicyclic core and the oxygen atoms of the hydroxyl and acetyl groups are disposed on the other side
A layered structure parallel to the ac plane is generated by O—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds plus C— HÁ Á Á(ring) interactions
H3Á Á ÁO1 and C16—H16CÁ Á ÁO2 hydrogen bonds (Table 1 and Fig. 2). These are connected into layers parallel to the ac plane by C21—H21AÁ Á ÁO2, C22—H22AÁ Á ÁO3 and C24— H24BÁ Á ÁO4 hydrogen bonds as well as C22—H22BÁ Á ÁCg1 interactions (Table 1 and Fig. 3)

Summary

Chemical context

Some tetrahydroisoquinoline (THISQ) based compounds are of medicinal and biological importance, being used as antitumoral (Pingaew et al, 2014; Castillo et al, 2018), antifungal (Scott et al, 2002) and anti-inflammatory agents (Siegfried et al, 1989). The THISQ core can be functionalized to build other heterocyclic rings on the carbocyclic ring (Xu et al, 2002; Carroll et al, 2007; Demers et al, 2008, Marae et al, 2021a). We have used some compounds related to THISQ as durable fluorescent dyes for cotton (Marae et al, 2021b). The widespread importance of these compounds motivated us to further study the THISQ core. H3Á Á ÁO1 and C16—H16CÁ Á ÁO2 hydrogen bonds (Table 1 and Fig. 2). These are connected into layers parallel to the ac plane by C21—H21AÁ Á ÁO2, C22—H22AÁ Á ÁO3 and C24— H24BÁ Á ÁO4 hydrogen bonds as well as C22—H22BÁ Á ÁCg1 interactions (Table 1 and Fig. 3)

Structural commentary

Hirshfeld surface analysis

Database survey

Findings

Synthesis and crystallization