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2‐[(E)‐(4‐Chloro­phenyl)­methyl­ene­amino]‐N‐(X‐methyl­phenyl)‐4,5,6,7‐tetra­hydro‐1‐benzo­thio­phene‐3‐carbox­amide,where X = 2 and 3
Authors:Vasu  K A Nirmala  Deepak Chopra  S Mohan  J Saravanan
Abstract:The title compounds, both C23H21ClN2OS, are isomeric, with (I) and (II) being the N‐3‐methyl­phenyl and N‐2‐methyl­phenyl derivatives, respectively. The dihedral angle between the 4‐chloro­phenyl group and the thio­phene ring in (II) 38.1 (1)°] is larger than that in (I) 7.1 (1)°], indicating steric repulsion between the chloro­phenyl and o‐toluidine groups in (II). In both compounds, an intramolecular N—H?N hydrogen bond forms a pseudo‐six‐membered ring, thus locking the molecular conformation. In the crystal structures, mol­ecules are connected via N—H?O hydrogen bonds, forming chains along the b axis in (I) and along the c axis in (II). Intermolecular C—H?O/S and π–π interactions are also observed in (II), but not in (I).
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