Abstract
A novel Schiff base compound, C20H27NO2, was obtained by a condensation of rimantadine and 2-hydroxy-4-methoxybenzaldehyde. An intramolecular O—H⋯N hydrogen bond supports the phenol–imine tautomeric form. The adamantane and iminomethyl-4-methoxyphenol units are arranged in a folded conformation [C—N—C—C torsion angle = 110.9 (3)°]. In the crystal, highly hydrophobic adamantane moieties are inserted between the iminomethyl-4-methoxyphenol units in a sandwich-like arrangement along the c axis.
Highlights
A novel Schiff base compound, C20H27NO2, was obtained by a condensation of rimantadine and 2-hydroxy-4-methoxybenzaldehyde
The adamantane and iminomethyl-4-methoxyphenol units are arranged in a folded conformation [C—N—C—C torsion angle =
Highly hydrophobic adamantane moieties are inserted between the iminomethyl-4-methoxyphenol units in a sandwich-like arrangement along the c axis
Summary
Xu-Dong Jin,a* Hai-Bo Wanga and Yue-Hong Jinb a College of Chemistry, Liaoning University, Shenyang 110036, People’s Republic of. BLiaoning Provincial Institute of Measurement, Shenyang 110004, People’s Republic of China. R factor = 0.046; wR factor = 0.137; data-to-parameter ratio = 14.4. A novel Schiff base compound, C20H27NO2, was obtained by a condensation of rimantadine and 2-hydroxy-4-methoxybenzaldehyde. An intramolecular O—H N hydrogen bond supports the phenol–imine tautomeric form. The adamantane and iminomethyl-4-methoxyphenol units are arranged in a folded conformation [C—N—C—C torsion angle =. Highly hydrophobic adamantane moieties are inserted between the iminomethyl-4-methoxyphenol units in a sandwich-like arrangement along the c axis. Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL
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