(Z)-1-[(3-Cyano­phen­yl)iminiometh­yl]-2-naphtholate

Yong-Feng Zhao; Jin-Ping Xiong; Yu Zuo

doi:10.1107/S1600536809020224

. 2009 Jun 6;65(Pt 7):o1477. doi: 10.1107/S1600536809020224

(Z)-1-[(3-Cyanophenyl)iminiomethyl]-2-naphtholate

Yong-Feng Zhao ^a, Jin-Ping Xiong ^a,^*, Yu Zuo ^a

PMCID: PMC2969241 PMID: 21582779

Abstract

The title compound, C₁₈H₁₂N₂O, crystallizes in a zwitterionic form. The dihedral angle between the planes of the benzene ring and naphthalene ring system is 13.95 (5)°. An intramolecular N—H⋯O interaction results in the formation of a planar six-membered ring, which is oriented at dihedral angles of 13.50 (4) and 4.49 (4)° with respect to the benzene ring and naphthalene ring system, respectively. In the crystal structure, intermolecular C—H⋯O and C—H⋯N interactions link the molecules into a two-dimensional network. π–π contacts between the naphthalene systems [centroid–centroid distance = 3.974 (1) Å] may further stabilize the structure.

Related literature

For the pharmacological activity of Schiff base compounds, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶). For the role played by Schiff base compounds in coordination chemistry related to magnetism, see: Chen et al. (2008 ▶); Weber et al. (2007 ▶). For related structures, see: Elmali et al. (2001 ▶); Yüce et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₂N₂O
M _r = 272.30
Triclinic,
a = 7.8943 (16) Å
b = 9.1356 (18) Å
c = 9.4933 (19) Å
α = 83.97 (3)°
β = 84.41 (3)°
γ = 82.50 (3)°
V = 672.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.976, T _max = 0.983
6177 measured reflections
2628 independent reflections
1146 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.195
S = 0.94
2628 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.24 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020224/hk2700sup1.cif

e-65-o1477-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020224/hk2700Isup2.hkl

e-65-o1477-Isup2.hkl^{(129.1KB, 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—H1A⋯O1	0.86	1.87	2.562 (3)	136
C2—H2A⋯N2ⁱ	0.93	2.61	3.463 (3)	152
C6—H6A⋯O1ⁱⁱ	0.93	2.57	3.376 (3)	145
C17—H17A⋯N2ⁱ	0.93	2.62	3.522 (3)	163

Open in a new tab

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

supplementary crystallographic information

Comment

Schiff base compounds have received considerable attention for many years, primarily due to various pharmacological activities, such as anticancer (Dao et al., 2000) and anti-HIV (Sriram et al., 2006) activities. In addition, Schiff base compounds play important roles in coordination chemistry related to magnetism (Weber et al., 2007) and catalysis (Chen et al., 2008). Generally, Schiff base compounds exhibit the phenol-imine and keto-amine forms. Another form of the Schiff base compounds is their zwitterionic form, and this form have been reported in the literature (Elmali, et al., 2001). We report herein the crystal structure of the title compound.

The molecule of the title compound (Fig 1) is in a zwitterionic form. The bond lengths (Allen et al., 1987) and angles are within normal ranges, and C8=N1 [1.304 (4) Å] and C10-O1 [1.287 (4) Å] bonds may be compared with the corresponding values [1.2954 (19) and 1.2946 (17) Å] in a similar zwitterionic structure (Yüce et al., 2006). Phenyl and naphthalyl rings, A (C1-C6) and B (C9-C18), are, of course, planar and the dihedral angle between them is 13.95 (5)°. Intramolecular N-H···O interaction (Table 1) results in the formation of a planar six-membered ring C (O1/N1/C8-C10/H1A), which is oriented with respect to rings A and B at dihedral angles of 13.50 (4) and 4.49 (4) °, respectively.

In the crystal structure, intramolecular N-H···O and intermolecular C-H···O and C-H···N interactions (Table 1) link the molecules into a two-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the naphthalyl rings, Cg2—Cg2ⁱ [symmetry code: (i) -x, 1 - y, 1 - z, where Cg2 is centroid of the ring (C9-C13/C18)] may further stabilize the structure, with centroid-centroid distance of 3.974 (1) Å.

Experimental

For the preparation of the title compound, 3-aminobenzonitrile (0.59 g, 5 mmol) and 2-hydroxynaphthalene-1-carbaldehyde (0.861 g, 5 mmol) were dissolved in ethanol (25 ml). The resulting mixture was heated to reflux for 6 h, and then cooled to room temperature. The solid product was collected by filtration. Crystals suitable for X-ray analysis were obtained on slow evaporation at room temperature.