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5-Amino-1-naphthol: Two-Dimensional Sheets Built Up From R(4)(4)(18) Rings Formed by O-H...N, N-H...O and Pi-Pi Interactions

5-Amino-1-naphthol: Two-Dimensional Sheets Built Up From R(4)(4)(18) Rings Formed by O-H...N, N-H...O and Pi-Pi Interactions

Ewa Rozycka-Sokolowska, Bernard Marciniak

Acta Crystallogr C. 2009 Nov;65(Pt 11):o565-8.

PMID: 19893237

Abstract:

The crystal structure of the title compound, C(10)H(9)NO, (I), contains intermolecular O-H...N and N-H...O hydrogen bonds which together form sheets parallel to the (001) plane containing rings with an unusual R(4)(4)(18) motif. These rings are additionally stabilized by an intermolecular pi-pi stacking interaction. The significance of this study lies in the comparison drawn between the molecular structure of (I) and those of related compounds (1,5-diaminonaphthalene, 8-amino-2-naphthol, 3-amino-2-naphthol and aniline), which shows a close similarity in the noncoplanar orientation of the amine group and the aromatic moiety. Comparison of the crystal structures of (I) and several of its simple analogues (1-naphthol, naphthalene-1,4-diol, naphthalene-1,5-diol and 4-chloro-1-naphthol) shows a close similarity in the packing of the molecules, which form pi-stacks along the shortest crystallographic axes with a substantial spatial overlap between adjacent molecules.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP604444	4-Chloro-1-naphthol		604-44-4	Price

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