2,2′-Dichloro-1,1′-[(pentane-1,5-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dibenzene

Wen-Kui Dong; Jun-Feng Tong; Jian-Chao Wu; Li Li; Jian Yao

doi:10.1107/S1600536809027433

. 2009 Jul 18;65(Pt 8):o1904. doi: 10.1107/S1600536809027433

2,2′-Dichloro-1,1′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene

Wen-Kui Dong ^a,^*, Jun-Feng Tong ^a, Jian-Chao Wu ^a, Li Li ^a, Jian Yao ^a

PMCID: PMC2977418 PMID: 21583594

Abstract

The molecule of the title compound, C₁₉H₂₀Cl₂N₂O₂, which lies across a crystallographic inversion centre, adopts a linear configuration. The dihedral angle between the two halves of the molecule is 5.14 (2)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link neighbouring molecules into an infinite zigzag chain supramolecular structure.

Related literature

For background to Schiff base compounds in transition metal coordination chemistry, see: Granovski et al. (1993 ▶). For the properties of Schiff base–metal complexes, see: Ghosh et al. (2006 ▶); Ward (2007 ▶). For our work on the synthesis and structural characterization of Schiff base–bisoxime compounds, see: Dong et al. (2008a ▶). For related structures, see: Dong et al. (2008b ▶, 2009 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₂₀Cl₂N₂O₂
M _r = 379.27
Monoclinic,
a = 12.5025 (12) Å
b = 19.7801 (17) Å
c = 7.8085 (9) Å
β = 96.747 (1)°
V = 1917.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.45 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.857, T _max = 0.908
9529 measured reflections
3376 independent reflections
1631 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.116
S = 1.02
3376 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 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/S1600536809027433/hg2535sup1.cif

e-65-o1904-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027433/hg2535Isup2.hkl

e-65-o1904-Isup2.hkl^{(165.6KB, 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
C10—H10⋯O2ⁱ	0.93	2.60	3.527 (4)	177

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Foundation of the Education Department of Gansu Province and the ‘Jing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

supplementary crystallographic information

Comment

Schiff base compounds are one kind of important stereochemical models in transition metal coordination chemistry due to their ease of preparation and structural variations (Granovski et al., 1993) and play an important role in the development of coordination chemistry owing to forming stable complexes with most of the transition metals or nontransition metals, in which many could exhibit intresting properties, including magnetic, optics and catalysis (Ghosh et al., 2006; Ward et al., 2007). In view of these facts and in continuation of our works on the synthesis and structural characterization of Schiff base bisoxime compounds (Dong et al., 2008a), here we report synthesis and crystal structure of the title compound (Fig. 1).

The single-crystal structure of the title compound has a crystallographic inversion centre (symmetry code: -x, -y, -z) and twofold screw axis (symmetry code: -x, 1/2 + y, 1/2 - z), and adopts a linear configuration. This structure is not similar to what was observed in our previously reported series bisoxime compounds containing five-methene bridge, which assume a W-shape configuration (Dong et al., 2008b) and distorted Z configuration (Sun et al., 2009). The dihedral angle between the two halves of the molecule is 5.14 (2)°. Intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2) link the neighbouring molecules into an infinite zigzag chain supramolecular structure.

Experimental

2,2'-Dichloro-1,1'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]dibenzene was synthesized according to an analogous method reported earlier (Dong et al., 2009). To an ethanol solution (4 ml) of o-chlorobenzaldehyde (394.1 mg, 2.80 mmol) was added an ethanol absolute (3 ml) of 1, 5-bis(aminooxy)pentane (187.9 mg, 1.40 mmol). The mixture solution was stirred at 328 K for 8 h. After cooling to room temperature, no precipitate was formed, when the mixture solution was concentrated to about 1 ml under reduced pressure, and cooled to room temperature, the precipitate was filtered, and washed successively with ethanol and n-hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 119.1 mg of the title compound. Yield, 24.7%. m. p. 327–328 K. Anal. Calcd. for C₁₉H₂₀Cl₂N₂O₂: C, 60.17; H, 5.32; N, 7.39. Found: C, 60.10; H, 5.53; N, 7.27.

Colorless needle-like single crystals suitable for X-ray diffraction studies were obtained after one month by slow evaporation from a methanol solution of the title compound.