1,4-Bis(4-chloro­phen­yl)-2-hydroxy­butane-1,4-dione

Yongjun Liu; Kuiwei Yang; Weiling Song; Yan Qi

doi:10.1107/S1600536810018027

. 2010 May 22;66(Pt 6):o1426. doi: 10.1107/S1600536810018027

1,4-Bis(4-chlorophenyl)-2-hydroxybutane-1,4-dione

Yongjun Liu ^a,^*, Kuiwei Yang ^a, Weiling Song ^a, Yan Qi ^a

PMCID: PMC2979451 PMID: 21579502

Abstract

In the title compound, C₁₆H₁₂Cl₂O₃, the benzene rings form a dihedral angle of 2.0 (3)°. Within the central O=C—CH₂C(H)OH—C=O unit, the carbonyl groups are coplanar and lie to opposite sides [O—C⋯C—O = −170.1 (6)°]. In the crystal, intermolecular O—H⋯O hydrogen bonds formed between the hydroxy groups lead to a supramolecular chain along the c axis. In addition, the crystal packing features some very weak C—H⋯π interactions.

Related literature

For the synthesis and applications of 1,4-dicarbonyl compounds, see: Ellison (1973 ▶); Hassner (1991 ▶); Ohno et al. (2001 ▶).

Experimental

Crystal data

C₁₆H₁₂Cl₂O₃
M _r = 323.16
Monoclinic,
a = 34.800 (8) Å
b = 7.4221 (14) Å
c = 5.6535 (13) Å
β = 95.925 (2)°
V = 1452.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 273 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.947, T _max = 0.964
3531 measured reflections
1256 independent reflections
998 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.163
S = 1.05
1256 reflections
190 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018027/tk2670sup1.cif

e-66-o1426-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018027/tk2670Isup2.hkl

e-66-o1426-Isup2.hkl^{(62.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1—C6 and C11—C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O2ⁱ	0.82	2.10	2.894 (6)	163
C1—H1⋯Cg1ⁱⁱ	0.93	2.89	3.507 (6)	125
C4—H4⋯Cg1ⁱⁱⁱ	0.93	2.97	3.600 (6)	126
C13—H13⋯Cg2ⁱⁱ	0.93	2.88	3.517 (6)	127
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.90	3.544 (6)	128

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

1,4-Dicarbonyl compounds constitute key intermediates in various natural product syntheses, and are important synthetic precursors of cyclopentenones, cyclopenta-1,3-diones, butenolides, and derivatives of furan and pyrrole (Hassner, 1991). For this reason, a number of methods for their synthesis have been developed and applied (Ellison, 1973; Ohno et al., 2001).

In the title compound, Fig. 1, the benzene rings form a dihedral angle of 2.0 (3) °. Intermolecular O2—H2A···O2 hydrogen bonds lead to the formation of a supramolecular chain along the c axis (Table 1, Fig. 2). In addition, the crystal packing is stabilized by intermolecular C—H···π interactions (Table 1) and short Cl···Clⁱ contacts (3.434 (3) Å for i: 1/2+x, 1/2-y, -1/2+z).

Experimental

The title compound was obtained as a by-product in the coupling reaction between 4-ClC₆H₄COCH₂Br and benzaldehyde, a reaction which is being studied in our laboratory. Colourless single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution over a period of 20 days.