1-[(Butyl­amino)(phen­yl)meth­yl]naphthalen-2-ol

Hen-Mei Ni

doi:10.1107/S1600536811000067

. 2011 Jan 12;67(Pt 2):o322. doi: 10.1107/S1600536811000067

1-[(Butylamino)(phenyl)methyl]naphthalen-2-ol

Hen-Mei Ni ^a,^*

PMCID: PMC3051726 PMID: 21523008

Abstract

In the title compound, C₂₁H₂₃NO, obtained via a one-pot synthesis, an intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The dihedral angle between the fused ring system and the phenyl ring is 78.27 (5)°. The crystal packing is characterized by helical chains of molecules linked by C—H⋯O hydrogen bonds.

Related literature

For applications of Betti-type reactions, see: Zhao et al. (2004 ▶); Lu et al. (2002 ▶); Xu et al. (2004 ▶); Wang et al. (2005 ▶)

Experimental

Crystal data

C₂₁H₂₃NO
M _r = 305.40
Orthorhombic,
a = 10.842 (7) Å
b = 16.651 (7) Å
c = 9.787 (6) Å
V = 1766.9 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.856, T _max = 1.000
14129 measured reflections
3121 independent reflections
1998 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.087
wR(F ²) = 0.134
S = 1.02
3121 reflections
211 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000067/gw2088sup1.cif

e-67-0o322-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000067/gw2088Isup2.hkl

e-67-0o322-Isup2.hkl^{(153.2KB, 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
O1—H1A⋯N1	0.82	1.89	2.580 (5)	142

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Acknowledgments

This work was supported by a start-up grant to the author.

supplementary crystallographic information

Comment

Over one hundred years ago, Betti developed a straightforward synthesis involving the condensation of 2-naphthol, ammonia and equivalents of benzaldehyde, followed by the addition of HCl and KOH to yield 1-(a-aminobenzyl)-2-naphthol. This product which possesses an asymmetric carbon center is known as a Betti base (Zhao & Li et al. 2004). Betti-type reaction is an important method to synthesize chiral ligands and by this method many unnatural homochiral amino-phenol compounds have been obtained (Lu et al. 2002; Xu et al. 2004; Wang et al. 2005). Here we report the synthesis and crystal structure of the title compound (Fig. 1), obtained by a three-component condensation reaction of 2-naphthol, benzaldehyde and butan-1-amine under solvent-free condition.

Molecules of the title compound have normal geometric parameters. The bond lengths and angles are within their normal ranges. The rings A (C1–C10) and B (C12–C17) are, of course, planar and the dihedral angle between them is A/B = 78.27 (5). As can be seen from the packing diagram (Fig. 2), the intramolecular O—H···N hydrogen bond seems to be effective in the stabilization of the crystal structure. Dipole–dipole and van der Waals interactions are effective in the molecular packing.

Experimental

benzaldehyde (1.59 g, 0.015 mol) and butan-1-amine (1.095 g, 0.015 mol) was added to 2-naphthol (2.16 g, 0.015 mol) without solvent under nitrogen. The temperature was raised to 120°C in one hour gradually and the mixture was stirred at this temperature for 10 h. The system was treated with 20 ml of ethanol 95% and cooled. The precipitate was filtered and washed with a small amount of ethanol 95%. The title compound was isolated using column chromatography (Petroleum ether: ethyl acetate-2:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of ethyl acetate solution.