Acta Crystallographica Section C

Crystal Structure Communications

Volume 59, Part 12 (December 2003)

Acta Cryst. (2003). C59, o676-o678 [doi:10.1107/S0108270103023205]

Two biologically active thiophene-3-carboxamide derivatives

Vasu, K. A. Nirmala, A. R. Choudhury, S. Mohan, J. Saravanan and T. Narasimhamurthy

Abstract: The two title compounds, 2-({(1Z)-[4-(dimethylamino)phenyl]methylene}amino)-4,5-dimethyl-N-(2-methylphenyl)thiophene-3-carboxamide, C₂₃H₂₅N₃OS, (I), and 2-({(1E)-[4-(dimethylamino)phenyl]methylene}amino)-N-(4-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide,C₂₅H₂₇N₃OS, (II), show antibacterial and antifungal activities. The asymmetric unit of (II) contains two crystallographically independent molecules. The o-toluidine ring in (I) lies gauche with respect to the thiophene ring. In (II), the p-toluidine ring is coplanar with the thiophene ring in one molecule, but is tilted from it in the other molecule. Neither structure exhibits any significant intermolecular interactions, but in both, an intramolecular N-HN hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and removing conformational flexibility.

Formula: C₂₃H₂₅N₃OS and C₂₅H₂₇N₃OS

Online 8 November 2003


	Structure factor file (CIF format) (178.9 kbytes) Contains datablock I

	Structure factor file (CIF format) (419.7 kbytes) Contains datablock II

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