Bis(2-hydroxy­benzaldehyde oxime) O,O′-butane-1,4-diyldicarbonyl ether

Bijan Etemadi; Reza Kia; Hashem Sharghi; Mona Hosseini Sarvari

doi:10.1107/S1600536809016663

. 2009 May 20;65(Pt 6):o1309. doi: 10.1107/S1600536809016663

Bis(2-hydroxybenzaldehyde oxime) O,O′-butane-1,4-diyldicarbonyl ether

Bijan Etemadi ^a,^*, Reza Kia ^a,^‡, Hashem Sharghi ^b, Mona Hosseini Sarvari ^b

PMCID: PMC2969837 PMID: 21583166

Abstract

The molecule of the title compound, C₂₀H₂₀N₂O₆, lies across a crystallographic inversion centre, the asymmetric unit comprising one half-molecule. An intramolecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. Pairs of intermolecular C—H⋯O hydrogen bonds link neighbouring molecules into a layer with R ² ₂(38) ring motif. The crystal structure is further stabilized by the intermolecular C—H⋯π interactions.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For hydrogen bond motifs, see Bernstein et al. (1995 ▶). For Schiff bases, see: Granovski et al., (1993 ▶). For the synthesis, see: Hosseini Sarvari (2003 ▶).

Experimental

Crystal data

C₂₀H₂₀N₂O₆
M _r = 384.38
Monoclinic,
a = 13.0293 (11) Å
b = 5.5464 (4) Å
c = 25.538 (2) Å
β = 91.348 (7)°
V = 1845.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.45 × 0.11 × 0.10 mm

Data collection

STOE IPDSII diffractometer
Absorption correction: numerical (X-RED32; Stoe & Cie (2005 ▶) T _min = 0.956, T _max = 0.985
10357 measured reflections
2493 independent reflections
2098 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.099
S = 1.10
2493 reflections
135 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016663/at2778sup1.cif

e-65-o1309-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016663/at2778Isup2.hkl

e-65-o1309-Isup2.hkl^{(120.1KB, 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
O1—H1⋯N1	0.91 (3)	1.79 (3)	2.5836 (15)	144 (2)
C4—H4⋯O1ⁱ	0.93	2.45	3.1874 (17)	136
C2—H2⋯Cg1ⁱⁱ	0.93	2.75	3.4659 (14)	134

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C1–C6 benzene ring.

Acknowledgments

We thank Shiraz University for financial support.

supplementary crystallographic information

Comment

Schiff base compounds are some of the most important stereochemical models in transition metal coordination chemistry, with their ease of preparation and structural variations (Granovski et al., 1993). In continuation of our works on the synthesis and structural characterization of Schiff base ligands here we report the structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, lies across a crystallographic inversion centre. Intramolecular O—H···N hydrogen bond generates a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). Pairs of intermolecular C—H···O hydrogen bonds link neighbouring molecules into a layer with R²₂(38) ring motif (Fig. 2). The crystal structure is further stabilized by the intermolecular C—H···π interactions [Cg1 is the centroid of the C1–C6 benzene ring] (Table 1).

Experimental

An ethyl acetate solution (40 ml) of salicylaldoxime (2 mmol, 768 mg) was treated with butanedicarboxylic acid chloride (1 mmol, 183 mg) at -5 ⁰ C. The mixture was stirred for 30 min and then filtered and the resulting white powder dried under air (Hosseini Sarvari, 2003). Single crystals suitable for X-ray diffraction were obtained from an ethanol solution.