Title of article :
Crystal structures of (E)-3-(furan-2-yl)-2-phenyl-N-tosylacrylamide and (E)-3-phenyl-2-(m-tolyl)-N-tosylacrylamide
Author/Authors :
Cheng, Dong School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China , Meng, Xiangzhen School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China , Sheng, Zeyuan School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China , Wang, Shuangming School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China , Duan, Yuanyuan School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China , Li, Ziqian School of Chemistry and Materials Engineering - Chaohu College - Chaohu Anhui, People's Republic of China
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 :
C—H⋯π interactions , inversion dimers , N—H⋯O hydrogen bonding , CuAAC , Cu-catalysed azide-alkyne cycloaddition reaction , crystal structure
Journal title :
Acta Crystallographica Section E: Crystallographic Communications