2,2′-[1,1′-(Propane-1,3-diyldioxy­dinitrilo)diethyl­idyne]di-1-naphthol

Wen-Kui Dong; Jian-Chao Wu; Yin-Xia Sun; Li Li; Jian Yao

doi:10.1107/S1600536809023241

. 2009 Jun 20;65(Pt 7):o1657. doi: 10.1107/S1600536809023241

2,2′-[1,1′-(Propane-1,3-diyldioxydinitrilo)diethylidyne]di-1-naphthol

Wen-Kui Dong ^a,^*, Jian-Chao Wu ^a, Yin-Xia Sun ^a, Li Li ^a, Jian Yao ^a

PMCID: PMC2969260 PMID: 21582919

Abstract

The molecule of the title compound, C₂₇H₂₆N₂O₄, lies across a crystallographic inversion centre and adopts an l-shaped configuration. Within the molecule, the two naphthalene units are approximately perpendicular, making a dihedral angle of 80.24 (5)°. The two intramolecular O—H⋯N hydrogen bonds, generate S(6) ring motifs. In the crystal structure, every molecule links five other molecules into an infinite cross-linked layered supramolecular structure via intermolecular C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π stacking interactions [centroid–centroid distance = 3.956 (4) Å].

Related literature

For the steric and electronic properties of Schiff bases, see: Yamada (1999 ▶). For background to this study, see: Dong et al. (2006 ▶). For related structures, see: Dong & Duan (2008 ▶); Dong et al. (2008a ▶,b ▶,c ▶,d ▶); Duan et al. (2007 ▶); He et al. (2008 ▶).

Experimental

Crystal data

C₂₇H₂₆N₂O₄
M _r = 442.50
Triclinic,
a = 7.4411 (10) Å
b = 8.8911 (16) Å
c = 18.106 (2) Å
α = 100.645 (1)°
β = 94.331 (1)°
γ = 106.329 (2)°
V = 1119.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.42 × 0.37 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.957, T _max = 0.968
5800 measured reflections
3876 independent reflections
2325 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.145
S = 1.04
3876 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 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/S1600536809023241/hg2527sup1.cif

e-65-o1657-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023241/hg2527Isup2.hkl

e-65-o1657-Isup2.hkl^{(190KB, 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
O3—H3⋯N1	0.82	1.83	2.543 (2)	145
O4—H4⋯N2	0.82	1.82	2.540 (2)	146
C12—H12⋯O3ⁱ	0.93	2.68	3.588 (3)	166
C1—H1B⋯Cg1ⁱⁱ	0.97	2.78	3.480 (2)	129

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C6–C15 ring.

Acknowledgments

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

supplementary crystallographic information

Comment

Schiff bases are compounds containing the azomethine group, –R,R'C=N, prepared by the condensation reaction of a primary amine with active carbonyl group. Due to the versatility of their steric and electronic properties (Yamada, 1999), which can be fine tuned by choosing the appropriate amine and the substituents on an aromatic ring of the carbonyl compound, Schiff base bisoxime compounds have gained increased interest in the field of coordination chemistry (Dong et al., 2008a; He et al., 2008). As a part of our ongoing research (Dong et al., 2006; Duan et al., 2007), the synthesis and crystal structure of the title compound was reported (Fig. 1).

The molecule of the title compound lies across a crystallographic inversion centre (symmetry code: -x, -y, -z) and adopts an L-shaped configuration. This structure is not similar to what was observed in our previously reported series oxime compounds containing four-methene bridge, which always adopt a V-shaped configurations (Dong et al., 2006; Duan et al., 2007; Dong et al., 2008a; Dong & Duan, 2008; Dong et al., 2008b; Dong et al., 2008d; Dong et al., 2008c; He et al., 2008). Within the molecule, the dihedral angle between the plane of oxime functional groups and naphthalene ring is 8.93 (3)° for C6—C15 ring and O1—N1—C5, 5.30 (3)° for C18—C27 ring and O2—N2—C17, respectively. And the two naphthalene units are approximately vertical with the dihedral angle of 80.24 (5)°. The two intramolecular hydrogen bonds, O3—H3···N1 and O4—H4···N2,generate S(6) ring motifs helping to the stabilization of the title molecule.

In the crystal structure, the crystals are held together by an intermolecular C—H···π interaction and C12—H12···O3 hydrogen bonds between the phenolic-oxygen atom and the hydrogen of the naphthalene ring, in which the C1—H1B···π centroid separations are equal 2.782 Å involving the naphthalene ring C6—C15 (centroid, Cg1). In addition, the adjacent aromatic rings are further linked by the intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.596 (4) Å]. Thus, every title compound molecule links five other molecules into an infinite crosslinked layer supramolecular structure via intermolecular C—H···O hydrogen bonds, C—H···π and π–π stacking interactions (Fig. 2).

Experimental

2,2'-[(Propane-1,3-diyldioxy)bis(nitriloethylidyne)]dinaphthol was synthesized according to an analogous method reported earlier (Dong et al., 2008 e). To an ethanol solution (5 ml) of 2-acetyl-1-naphthol (388.5 mg, 2.06 mmol) was added dropwise an ethanol solution (3 ml) of 1,3-bis(aminooxy)propane (109.7 mg, 1.03 mmol). The mixture solution was stirred at 328–333 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 320.4 mg (Yield, 70.0%) of powder; m.p. 439–441 K. Colorless block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of ethyl acetate of 2,2'-[(propane-1,3-diyldioxy)bis(nitriloethylidyne)]dinaphthol at room temperature for about one month. Anal. Calcd. for C₂₇H₂₆N₂O₄: C, 73.28; H, 5.92; N, 6.33; Found: C, 73.25; H, 5.97; N, 6.29.