2‐[(E)‐(4‐Chlorophenyl)methyleneamino]‐N‐(X‐methylphenyl)‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carboxamide,where X = 2 and 3 |
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Authors: | Vasu K. A. Nirmala Deepak Chopra S. Mohan J. Saravanan |
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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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