1,1′-{2,2′-[1,4-Phenyl­enebis(methyl­ene)]bis­(­oxy)bis­(2,1-phenyl­ene)}diethanone

Nassir N N Al-Mohammed; Yatimah Alias; Zanariah Abdullah; Hamid Khaledi

doi:10.1107/S1600536811042528

. 2011 Oct 22;67(Pt 11):o3016. doi: 10.1107/S1600536811042528

1,1′-{2,2′-[1,4-Phenylenebis(methylene)]bis(oxy)bis(2,1-phenylene)}diethanone

Nassir N N Al-Mohammed ^a, Yatimah Alias ^a, Zanariah Abdullah ^a, Hamid Khaledi ^a,^*

PMCID: PMC3247415 PMID: 22220033

Abstract

The asymmetric unit of the title compound, C₂₄H₂₂O₄, contains one half-molecule, the other half being generated by a crystallographic center of inversion. The central benzene ring makes a dihedral angle of 72.49 (5)° with the terminal benzene ring. In the crystal, adjacent molecules are linked through C—H⋯O interactions, forming a sheet structure parallel to the bc plane. The sheets are stacked along the a axis via π–π interactions formed between the terminal benzene rings [centroid–centroid separation = 3.7276 (6) Å].

Related literature

For related structures, see: Hu (2010 ▶); Tang et al. (2008 ▶).

Experimental

Crystal data

C₂₄H₂₂O₄
M _r = 374.42
Orthorhombic,
a = 6.8490 (1) Å
b = 15.0815 (2) Å
c = 17.8519 (3) Å
V = 1843.98 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.969, T _max = 0.986
15454 measured reflections
2013 independent reflections
1728 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.100
S = 1.06
2013 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042528/is2792sup1.cif

e-67-o3016-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042528/is2792Isup2.hkl

e-67-o3016-Isup2.hkl^{(99.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042528/is2792Isup3.cml

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
C7—H7⋯O1ⁱ	0.95	2.56	3.4649 (14)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

supplementary crystallographic information

Comment

The title compound was obtained through the condensation of α,α'-dibromo-p-xylene with two equivalents of 2'-hydroxyacetophenone. The compound has a centrosymmetric molecular structure, the centroid of the central aromatic ring being located on an inversion center. The central aromatic ring makes a dihedral angle of 72.49 (5)° with the terminal rings. This value is comparable to those observed in similar structures (Hu, 2010; Tang et al., 2008). In the crystal, the adjacent molecules are linked through C—H···O interactions (Table 1) to form a sheet parallel to the bc plane (Fig. 2). The sheets are connected into a three-dimensional network viaπ–π interactions formed between the terminal rings in the a direction [centroid-centroid separation = 3.7276 (6) Å].

Experimental

To a suspension of α,α'-dibromo-p-xylene (1 g, 3.8 mmol) and potassium carbonate (1.05 g, 7.6 mmol) in dry acetone (25 ml), 2'-hydroxyacetophenone (1.03 g, 7.6 mmol) was added portionwise and the mixture was refluxed for 48 hr. The solvent was then evaporated under reduced pressure and the crude material was extracted by dichloromethane (3 × 25 ml). The combined organic layers was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum and the formed amorphous solid was re-crystallized from chloroform to obtain off-white crystals of the title compound (m.p. = 435–437 K).