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Crystal packing in salts of 1-adamantylamine and 1, 3, 5-trihydroxy-2, 4, 6-trinitrobenzene

While trinitro derivatives of phenols and their salts have been known since the 18th century, their use in crystal engineering, with exception of picric acid [1] has not been studied in detail, even though their planar structure with modifiable positions of strong and weak hydrogen bond acceptors and high acidity make them very versatile building blocks. The phenol derivative used in this study was 1, 3, 5-trihydroxy-2, 4, 6- trinitrobenzene (H3tnpg), a strong triprotic acid. This was crystalized with 1-adamantylamine (Ad), an organic base with a bulky, spherical, nonpolar alkyl group. Salts of various stoichiometries were prepared from various solvents. The deprotonation H3tnpg in the solids was found to vary primarily on the solvent used and only sometimes could be controlled by the relative amount of Ad used. Three distinctive types of crystal packing were observed, usually stabilized by solvent molecules entering voids between adamantyl groups. [1] V. Stilinović, B. Kaitner, Cryst. Growth Des. 11 (2011) 4110.

1-adamantylamine, 1, 3, 5-trihydroxy-2, 4, 6-trinitrobenzene, crystal packing

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