Crystal structures of 1-(4-chlorophenyl)-4-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid and 4-(4-methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

Abstract

In the title compounds C23H21ClN2O3 [I, namely 1-(4-chlorophenyl)-4-(4-methylphenyl)-3,8-dioxo-1,2,5,6,7,8-hexahydroquine-3-carboxylic acid] and C24H22N2O3 [II, namely 4-(4-methoxyphenyl)-1-(4-methylphenyl)-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile], each of the cyclohexene and dihydropyridine rings of the 1,2,5,6,7,8-hexahydroquinoline moieties adopts a twisted-boat conformation. The asymmetric units of both compounds I and II consist of two independent molecules (A and B). In IIA, three carbon atoms of the cyclohexene ring are disordered over two sets of sites in a 0.670 (11):0.330 (11) occupancy ratio. In the crystal of I, molecules are linked through classical N—H...O hydrogen bonds, forming inversion dimers with an R22(8) ring motif and with their molecular planes parallel to the crystallographic (020) plane. Non-classical C—H...O hydrogen-bonding interactions connect the dimers, resulting in a three-dimensional network. In the crystal of II, molecules are linked by C—H...N, C—H...O and C—H...π interactions, forming a three-dimensional network.

Keywords

• crystal structure
• cyclohexene ring
• dihydropyridine ring
• hexahydroquinoline ring
• dimer