Abstract
The title compound, C31H46NO7+·Cl-, was synthesized by a one-pot Mannich condensation reaction. In the mol-ecule, the piperidinone ring adopts a chair conformation, and the trimeth-oxy-substituted benzene rings and octyl chain are arranged equatorially. In the crystal, centrosymmetric dimers are linked into layers parallel to (011) by N-H⋯Cl and C-H⋯Cl hydrogen bonds. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are O⋯H (20.5%) inter-actions followed by C⋯H (7.8%), Cl⋯H (5.5%), C⋯C (1.2%), C⋯O (0.5%) and Cl⋯O (0.4%) inter-actions.
Highlights
Centrosymmetrically-related molecules are linked into dimers through pairs of N—HÁ Á ÁO hydrogen bonds (Table 1) forming rings with an R22(16) graph-set motif
The dimers are further connected by N—HÁ Á ÁCl and C— HÁ Á ÁCl hydrogen interactions, forming layers parallel to the (011) plane (Fig. 2)
Two-dimensional fingerprint plots are shown in Fig. 4 with a broad hump showing HÁ Á ÁH contacts and intense spikes indicating a strong OÁ Á ÁH interaction, while the broadening in the wing of the CÁ Á ÁH interaction is due to the presence of a ClÁ Á ÁH interactionÁThe largest contribution is from HÁ Á ÁH interactions (64.1%), followed by OÁ Á ÁH interactions, contributing 20.5%
Summary
Piperidine is a naturally occurring bioactive alkaloid (Hu et al, 2002; Finke et al, 2001; Taniguchi & Ogasawara, 2000) and the heterocyclic six-membered nitrogen-containing piperidine ring is an essential structural part of many important drugs including paroxetine, raloxifene, haloperidol, droperidol and minoxidiln (Wagstaff et al, 2002). 2,6-Diphenyl-substituted piperdine-4-one derivatives are important because of their potential biological activities such as antitumor, antimicrobial, analgesic, local anesthetic, antidepressant and anti-inflammatory (Kalai et al, 2011; Leonova et al, 2010; El-Subbagh et al, 2000; Jerom & Spencer, 1988). 2,6-Diphenyl-substituted piperdine-4-one derivatives are important because of their potential biological activities such as antitumor, antimicrobial, analgesic, local anesthetic, antidepressant and anti-inflammatory (Kalai et al, 2011; Leonova et al, 2010; El-Subbagh et al, 2000; Jerom & Spencer, 1988). This wide range of biological activities prompted us to synthesize novel 2,6-diphenyl piperdine-4-one derivatives with enhanced biological activities. In a continuation of this work, the title compound was synthesized using a one-pot Mannich condensation reaction as reported by Noller & Baliah (1948).
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