Abstract
In the title mol-ecular salt, C20H19N2S+·I-, prepared by the reaction of 1,3-di-phenyl-thio-urea and benzyl iodide, the C-S-C thio-ether bond angle is 101.66 (9)° and electrons are delocalized over the N+= C-N skeleton. The dihedral angle between the aromatic rings attached to the N atoms is 40.60 (9)°. In the crystal, N-H⋯I hydrogen bonds link the components into [100] chains.
Highlights
In the title molecular salt, C20H19N2S+ÁIÀ, prepared by the reaction of 1,3diphenylthiourea and benzyl iodide, the C—S—C thioether bond angle is 101.66 (9) and electrons are delocalized over the N+ C—N skeleton
N—HÁ Á ÁI hydrogen bonds link the components into [100] chains
Structural commentary The title compound, C20H19N2S+ÁIÀ (Fig. 1), is a molecular salt that arose from the reaction of 1,3-diphenylthiourea and benzyl iodide
Summary
Isothiouronium salts containing an R–S–C–(NHR)2+ moiety have been investigated as their hydrogen–bonding motifs for molecular recognition of anions (Yeo & Hong, 1998; Kubo et al, 2000; Kato et al, 2004; Nguyen et al, 2009; Nguyen & Kim, 2010) and as organocatalysts (Nguyen & Kim, 2011, 2012; Lee et al, 2018; Kang et al, 2019). As part of our work in this area, the synthesis and single-crystal structure of the title molecular salt, C20H19N2S+ÁIÀ are reported . 2. Structural commentary The title compound, C20H19N2S+ÁIÀ (Fig. 1), is a molecular salt that arose from the reaction of 1,3-diphenylthiourea and benzyl iodide. It is closer to that seen in diethyl sulfide [99.05 (4); Iijima et al, 1977] This result can be explained by the large dihedral angle between the benzene rings in the title compound. In the N-[(phenylamino)methylene]benzenaminium moiety of the title cation, the -electrons of the iminium double bond are delocalized over the N1—C6—N2 skeleton [the C8—N1 and C8—N2 bond distances are 1.319 (2) and 1.332 (2) A , respectively, and N1—C8—N2 = 124.53 (16)].
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