Crystal and molecular structure of 4,5-dimethyl-N-(2-methyl phenyl)-2-{[(1E)-3,4,5-trimethoxy phenylmethylene]amino}thiophene-3-carboxamide

Physics Department, Vivekananda Degree college, Malleshwaram west, Bangalore -560055, Bangalore University* Department of Physics, Bangalore University, Bangalore 560 056, Karnataka, India** Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India*** PES College of Pharmacy, Hanumanthanagar, Bangalore 560 050, Karnataka, India****
â—‹vasu sriranga vasu* K. A. Nirmala** Deepak Chopra*** S. Mohand**** J. Saravanan****

The title compound shows promising antibacterial activity against subtilis aureus, Escherichia coli compared with Ampicilin. The structure was determined by direct methods using SHELXS-97 and refined to a final R-value0.045. In the title compound, the geometry of the thiophene ring is planar and is good agreement with the data obtained for thiophene by electron diffraction. The o-toluidine is in the gauche position. The angle between thiophene and o-toluidine is 59.24(2)o. The S-C bond distances are not equal due to delocalisation. The methyl group of the p-methoxy connected to oxygen is not in the plane and is deviated from the phenyl plane by 0.095(1). The methyl groups attached at m-positions point away from each other. The inclination angles in the methoxy parts are not equal due to steric environment. The bond distances in the methoxy groups agree with values observed in other methoxy benzene derivatives. The non-planar part of the molecule i.e., o-toluidine is characterised by the torsion angle 72.84(2)o indicating the conformation of the o-toluidine is bent in the compound.

The molecular structure is primarily stabilized by intra-molecular N-H...O interactions forming pseudo-six membered S(6) ring forming hydrogen bonded pattern. The crystal packing is governed by a diverse set of C-H...O and π... π interactions. The dimers form a ring described by graph set analysis (12).