5-Amino-1-naphthol

Agnieszka Czapik; Arkadiusz Nitka; Maria Gdaniec

doi:10.1107/S1600536809045152

. 2009 Oct 31;65(Pt 11):o2964. doi: 10.1107/S1600536809045152

5-Amino-1-naphthol

Agnieszka Czapik ^a, Arkadiusz Nitka ^a, Maria Gdaniec ^a,^*

PMCID: PMC2971357 PMID: 21578535

Abstract

In the title compound, C₁₀H₉NO, the amino and the hydroxy groups act both as a single donor and a single acceptor in hydrogen bonding. In the crystal, molecules are connected via chains of intermolecular ⋯N—H⋯O—H⋯ interactions, forming a two-dimensional polymeric structure resembling the hydrogen-bonded molecular assembly found in the crystal structure of naphthalene-1,5-diol. Within this layer, molecules related by a translation along the a axis are arranged into slipped stacks via π–π stacking interactions [interplanar distance = 3.450 (4) Å]. The amino N atom shows sp ³ hybridization and the two attached H atoms are located on the same side of the aromatic ring.

Related literature

For the crystal structure of 1,5-dihydroxynaphthalene, see: Belskii et al. (1990 ▶). For amino-hydroxy group recognition and packing motifs of aminols, see: Ermer & Eling (1994 ▶); Hanessian et al. (1994 ▶); Allen et al. (1997 ▶); Dey et al. (2005 ▶).

Experimental

Crystal data

C₁₀H₉NO
M _r = 159.18
Orthorhombic,
a = 4.8607 (2) Å
b = 12.3175 (6) Å
c = 13.0565 (5) Å
V = 781.71 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 130 K
0.30 × 0.15 × 0.02 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer
Absorption correction: none
8484 measured reflections
963 independent reflections
726 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.091
S = 1.06
963 reflections
121 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045152/su2154sup1.cif

e-65-o2964-sup1.cif^{(13.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045152/su2154Isup2.hkl

e-65-o2964-Isup2.hkl^{(47.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11O⋯N12ⁱ	0.94 (3)	1.83 (3)	2.749 (3)	167 (3)
N12—H12B⋯O11ⁱⁱ	0.96 (3)	2.09 (3)	3.046 (3)	171 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Amino-hydroxy group recognition has been at the focus of crystal engineering since Ermer & Eling (1994) and Hanessian et al. (1994) noticed the complementarity of hydroxy and amino groups as regards hydrogen-bond donors and acceptors. Shortly after it was demonstrated with simple 1,2- and 1,3-aminophenols that molecular features, such as functional groups, do not necessarily result in a single manner of the molecular arrangement, and that strong N—H···O and O—H···N hydrogen bonding is frequently unable to exclude other factors from controlling the crystal packing (Allen et al., 1997; Dey et al. 2005). Here we report on the crystal structure of a simple aminonaphthol which, as regards the substitution pattern, can be considered as an analogue of 1,4-aminophenol.

The molecular structure of the title compound is shown in Fig. 1, and the geometrical parameters are available in the archived CIF. Whereas 1,4-aminophenol forms a tetrahedral network, via N—H···O and O—H···N hydrogen bonds (Ermer & Eling, 1994), in the title compound the molecules are connected via chains of ···N—H···O—H··· interactions to form a two-dimensional polymeric structure (Fig. 2, Table 1). The two-dimensional assembly of the molecules joined by hydrogen bonding resembles that formed by 1,5-dihydroxynaphthalene (Belskii et al., 1990). One amino H-atom is not involved in hydrogen bonding and does not take part in any other specific interactions.

Experimental

Single crystals of the commercially available 5-amino-1-naphthol (Aldrich) were obtained from chloroform solution by slow evaporation.