4,4′-(Propane-1,3-diyldi­oxy)dibenz­aldehyde

Qamar Ali; Muhammad Raza Shah; Seik Weng Ng

doi:10.1107/S1600536810021124

. 2010 Jun 9;66(Pt 7):o1620. doi: 10.1107/S1600536810021124

4,4′-(Propane-1,3-diyldioxy)dibenzaldehyde

Qamar Ali ^a, Muhammad Raza Shah ^a, Seik Weng Ng ^b,^*

PMCID: PMC3006695 PMID: 21587851

Abstract

The title compound, C₁₇H₁₆O₄, is a dialdehyde in which two formylphenoxy units are linked by a –CH₂CH₂CH₂– chain; the molecule is V-shaped with the middle methylene C atom as the apex. The two benzene rings are aligned at 77.4 (1)°. In the crystal, molecules are linked into centrosymmetric dimers by pairs of non-classical C—H⋯O hydrogen bonds.

Related literature

For background to Schiff bases derived by condensing similar dialdehydes with primary amines, see: Zhang et al. (2008 ▶). For the crystal structure of the 2,2′-disubstituted analog, see: Hu et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₆O₄
M _r = 284.30
Monoclinic,
a = 15.3323 (15) Å
b = 4.6173 (5) Å
c = 20.2800 (19) Å
β = 104.783 (1)°
V = 1388.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer
8297 measured reflections
3113 independent reflections
2538 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.03
3113 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021124/ci5094sup1.cif

e-66-o1620-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021124/ci5094Isup2.hkl

e-66-o1620-Isup2.hkl^{(152.8KB, 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
C16—H16⋯O1ⁱ	0.95	2.41	3.287 (2)	154

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the University of Karachi and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The two-arm aldehyde is intended for condensation with primary amines to form Schiff bases, which, in a subsequent step, will be reacted with β-cyclodextrin to furnish inclusion compounds. The idea for this theme draws on a report on such compounds of poly(Schiff bases) (Zhang et al., 2008). The flexibilty of the Schiff base can be controlled by varying the position of the formyl group; the title compound has the the formyl groups in the 4,4'-positions. The crystal structure of the 2,2'-substituted compound has been reported (Hu et al., 2005). The molecule of C₁₇H₁₆O₄ (Scheme I) is V-shaped with the middle methylene carbon as the apex (Fig. 1).

Experimental

4-Hydroxybenzaldehyde (1 g, 8.2 mmol) was dissolved in acetone (25 ml). To the solution was added potassium carbonate (2.3 g, 16.4 mmol). The mixture was heated for 1 h. 1,3-Dibromopropane (0.29 ml, 2.7 mmol) was added and the mixture heated for another hour. The mixture was set aside for 8 h. The solvent was removed and the solid material was extracted with ethyl acetate. The solvent was again removed and the product purified by column chromatography by using dichloromethane-hexane (1:4) as mobile phase. Single crystals were obtained by recrystallization from dichloromethane.