N‐(X‐Methylphenyl)‐2‐{(Z)‐[(2,3,4‐trimethoxyphenyl)methylidene]amino}‐4,5,6,7‐tetrahydro‐1‐benzothiophene‐3‐carboxamide,where X = 2 and 3 |
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Authors: | Govindaiah Darshan Deepak Chopra Janardhanan Saravanan |
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Abstract: | The title isomers, viz. the N‐(3‐methylphenyl)‐, (I), and N‐(2‐methylphenyl)‐, (II), derivatives, both C26H28N2O4S, adopt an E configuration that places the thiophene and trimethoxyphenyl groups on opposite sides of the C=N double bond, providing a suitable orientation for formation of an intramolecular N—H...N hydrogen bond. However, while the molecule in (I) is close to being planar, the N‐methylphenyl group in (II) is twisted significantly from the plane of the remainder of the molecule. Both crystal structures are essentially layered and there are no intermolecular N—H...O hydrogen bonds. Compound (I) has a significantly higher calculated density than (II) (1.340 cf 1.305 Mg m−3), indicating that the molecular packing in the meta isomer is overall more efficient than that in the ortho isomer. |
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