1-[(2-Anilinoeth­yl)iminiometh­yl]-2-naph­thol­ate

Yu-Mei Hao

doi:10.1107/S1600536809019096

. 2009 May 23;65(Pt 6):o1400. doi: 10.1107/S1600536809019096

1-[(2-Anilinoethyl)iminiomethyl]-2-naphtholate

Yu-Mei Hao ^a,^*

PMCID: PMC2969739 PMID: 21583245

Abstract

The title Schiff base compound, C₁₉H₁₈N₂O, was prepared by the reaction of equimolar quantities of 2-hydroxy-1-naphthaldehyde with N-phenylethane-1,2-diamine in a methanol solution. The molecule adopts a zwitterionic conformation with the naphthyl OH group deprotonated and the imine N atom protonated. An intramolecular N—H⋯O hydrogen bond forms between them. The dihedral angle between the benzene ring and the naphthyl system is 86.9 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For Schiff base coordination chemistry, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For related structures, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₈N₂O
M _r = 290.35
Monoclinic,
a = 27.511 (3) Å
b = 6.845 (2) Å
c = 8.543 (2) Å
β = 104.263 (2)°
V = 1559.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.986
4485 measured reflections
1753 independent reflections
1312 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.105
S = 1.06
1753 reflections
202 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019096/sj2625sup1.cif

e-65-o1400-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019096/sj2625Isup2.hkl

e-65-o1400-Isup2.hkl^{(86.4KB, 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
N1—H1⋯O1	0.907 (10)	1.84 (3)	2.582 (3)	137 (3)
N2—H2⋯O1ⁱ	0.86	2.43	3.043 (3)	129

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff base compounds are an important class of materials used in the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). They are also used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of several Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). In this paper, the new Schiff base title compound, (I), Fig. 1, is reported.

In (I), the H atom of the phenol group is transferred to the imine N atom, forming an intramolecular N–H···O hydrogen bond (Table 1). The dihedral angle between the benzene ring and the naphthyl ring is 86.9 (2)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure of the compound, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Experimental

2-Hydroxy-1-naphthylaldehyde (0.1 mmol, 17.2 mg) and N-phenylethane-1,2-diamine (0.1 mmol, 13.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.