mm -1. The structure was solved by the Patterson search method (as it could not be solved by heavyatom techniques or direct methods) and refined to an R factor of 0.083 for 615 visually measured reflections. The structure is stabilized by hydrogen bonding between the polar groups and van der Waals interactions between the non-polar groups. Of the three hydrogen bonds, two are weak as they are bifurcated.
View of the molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size.
The title compound, CI8H17NO4S , is a diltiazem-related compound. The molecular packing is predominantly stabilized by hydrogen bonding; amide groups hydrogen bond with adjacent molecules to form centrosymmetric dimers. The seven-membered ring is distorted, showing a twist-boat conformation. The benzene ring is planar but the methoxyphenyl ring deviates significantly from planarity. The relative configuration of the methoxyphenyl and acetoxy groups is gauche.
CommentThe title compound, (I), is a drug intermediate in the synthesis of diltiazem, (II), an enantiomerically pure
The compounds 2-{[(E)-(4-methoxyphenyl)methylene]amino}-N-(3-methylphenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3carboxamide, C 24 H 24 N 2 O 2 S, (I), and N-(4-methylphenyl)-2-{[(E)-(4-methylphenyl)methylene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, C 24 H 24 N 2 OS, (II), show antibacterial and antifungal activities. The m-toluidine ring in (I) and the p-toluidine ring in (II) are coplanar with their respective thiophene rings. In (I), an intermolecular CÐ HÁ Á ÁO hydrogen bond is present, whereas (II) does not exhibit any signi®cant intermolecular interactions. However, in both compounds, an intramolecular NÐHÁ Á ÁN hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and eliminating conformational¯exibility. Comment The design of compounds that possess important pharmacological properties, such as antibacterial, anticancer, anti-in¯amatory and antitoxic activities, is an important area of research, and Schiff bases (
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