Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosylacrylamide and (E)-3-phenyl-2-(m-tolyl)-N-tosylacrylamide

Abstract

In the title N-tosylacrylamide compounds, C20H17NO4S, (I), and C23H21NO3S, (II), the conformation about the C=C bond is E. The acrylamide groups, [–NH—C(=O)—C=C–], are almost planar, with the N—C—C=C torsion angle being −170.18 (14)° in (I) and −168.01 (17)° in (II). In (I), the furan, phenyl and 4-methylbenzene rings are inclined to the acrylamide mean plane by 26.47 (11), 69.01 (8) and 82.49 (9)°, respectively. In (II), the phenyl, 3-methylbenzene and 4-methylbenzene rings are inclined to the acrylamide mean plane by 11.61 (10), 78.44 (10) and 78.24 (10)°, respectively. There is an intramolecular C—H...π interaction present in compound (II). In the crystals of both compounds, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. In (I), the dimers are reinforced by C—H...O hydrogen bonds and linked by C—H...π interactions, forming chains along [011]. In the crystal of (II), the dimers are linked via C—H...O hydrogen bonds, forming chains along [100]. The chains are further linked by C—H...π interactions, forming layers parallel to (010).

Keywords

• crystal structure
• Cu-catalysed azide-alkyne cycloaddition reaction
• CuAAC
• N—H...O hydrogen bonding
• inversion dimers
• C—H...π interactions