2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphthol

Wen-Kui Dong; Jian-chao Wu; Jian Yao; Li Li; Shang-sheng Gong

doi:10.1107/S1600536809022508

. 2009 Jun 17;65(Pt 7):o1598. doi: 10.1107/S1600536809022508

2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol

Wen-Kui Dong ^a,^*, Jian-chao Wu ^a, Jian Yao ^a, Li Li ^a, Shang-sheng Gong ^a

PMCID: PMC2969397 PMID: 21582872

Abstract

The complete molecule of the title compound, C₂₆H₂₄N₂O₄, is generated by a crystallographic centre of inversion. There are two intramolecular O—H⋯N hydrogen bonds. In the crystal structure, intermolecular C—H⋯O hydrogen bonds result in zigzag chains.

Related literature

For the applications of Shiff base ligands, see: Calligaris & Randaccio (1987 ▶) For the applications bisoxime derivatives of salen-type compounds, see: Sun et al. (2004 ▶); Wang et al. (2007 ▶). For related structures, see: Dong et al. (2008a ▶,b ▶,c ▶);

Experimental

Crystal data

C₂₆H₂₄N₂O₄
M _r = 428.47
Monoclinic,
a = 12.6682 (18) Å
b = 9.3728 (15) Å
c = 18.335 (2) Å
β = 97.478 (2)°
V = 2158.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.39 × 0.37 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.966, T _max = 0.989
5220 measured reflections
1894 independent reflections
1027 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.122
S = 1.06
1894 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022508/hg2524sup1.cif

e-65-o1598-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022508/hg2524Isup2.hkl

e-65-o1598-Isup2.hkl^{(93.3KB, 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
O2—H2⋯N1	0.82	1.84	2.562 (3)	146
C10—H10⋯O2ⁱ	0.93	2.63	3.446 (3)	146

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge finanical support from the ‘Jing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University.

supplementary crystallographic information

Comment

There has been considerable interest in Schiff base ligand containing oxygen and imine nitrogen atoms due to their variety of applications, especially for catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Calligaris & Randaccio, 1987). salen-type compounds and its bisoxime derivatives are a new class of multidentate ligand, which can be used as elemental building blocks for construction of supramolecular structures via intermolecular hydrogen bonding or short contact interaction (Sun et al., 2004; Wang et al., 2007). As an extension of our work (Dong et al., 2008a; Dong et al., 2008b) on the structural characterization of salen-type bisoxime compounds, here report the synthesis and structure of the title compound (Fig. 1).

The single-crystal structure of the title compound is built up by discrete C₂₆H₂₄N₂O₄ molecules, in which all bond lengths are in normal ranges. The molecule has a crystallographic twofold rotation axis (symmetry code: -x, y, 1/2 - z) and screw axis (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z), and adopts a distorted E-configuration. This structure is similar to what was observed in our previously reported E-configuration compounds of 2,2'-[1,1'-Ethylenedioxybis(nitriloethylidyne)]diphenol (Wang et al., 2007). The dihedral angle formed by the two naphthalene rings in each molecule of the title compound is about 43.20 °. There are two intramolecular hydrogen bonds, O2—H2···N1 (d(O2—H2) = 0.82 Å, d(H2···N1) = 1.84 Å, d(O2···N1) = 2.562 (3) Å, <O2—H2···N1 = 146°). Besides in the crystal structure, four intermolecular hydrogen bonds, C10—H10···O2 (d(C10—H10) = 0.93 Å, d(H10···O2) = 2.63 Å, d(C10···O2) = 3.446 (3) Å, <C10—H10···O2 = 146°), link two other molecules into infinite zigzag supramolecular structure (Fig. 2).

Experimental

2,2'-[1,1'-Ethylenedioxybis(nitriloethylidyne)]dinaphthol was synthesized according to an analogous method reported earlier (Dong et al., 2008c). To an ethanol solution (5 ml) of 2-acetyl-1-naphthol (392.1 mg, 2.10 mmol) was added dropwise an ethanol solution (3 ml) of 1,2-bis(aminooxy)ethane (96.2 mg, 1.04 mmol). The mixture solution was stirred at 328–433 K for 72 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 313.7 mg (Yield, 70.1%) of powder; m.p. 471–472 K. Colorless block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of dichloromethane of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol at room temperature for about three weeks. Anal. Calc. for C₂₆H₂₄N₂O₄: C, 73.28; H, 5.92; N, 6.33; Found: C, 73.25; H, 5.97; N, 6.29.