Crystal structure and Hirshfeld surface analysis of N-{[diphenyl(vinyl)silyl]methyl}-2-methylpropan-2-ammonium chloride

Abstract

N-{[Diphenyl(vinyl)silyl]methyl}-2-methylpropan-2-amine, C19H25NSi, is a newly synthesized secondary aminomethylsilane that can be used, for example, to study carbolithiation reactions of vinylsilanes. Because the neutral compound did not crystallize well, the hydrochloride salt, C19H26NSi+·Cl−, was formed, in which the two chloride ions in the asymmetric unit have crystallographic \overline{1} site symmetry. An unusually long Si—C bond of 1.9117 (10) Å is observed in the cation, which may be ascribed to electronic effects due to the β N+ species. In the crystal, the cations and anions are linked by N—H...Cl hydrogen bonds to generate [001] chains. To further investigate the intermolecular interactions, a Hirshfeld surface analysis was performed, which showed that H...H, C...H/H...C and H...Cl/Cl...H contacts contribute 70.4, 20.0 and 8.3%, respectively.