Diethyl 2,5-diphenyl­furan-3,4-dicarboxyl­ate

Sheng-Li Hu; Yi-Cheng Le; Ling Huang

doi:10.1107/S1600536810045241

. 2010 Nov 10;66(Pt 12):o3116. doi: 10.1107/S1600536810045241

Diethyl 2,5-diphenylfuran-3,4-dicarboxylate

Sheng-Li Hu ^a,^*, Yi-Cheng Le ^b, Ling Huang ^a

PMCID: PMC3011628 PMID: 21589420

Abstract

In the title compound, C₂₂H₂₀O₅, the substituted benzene rings are twisted away from the furan ring, making dihedral angles of 54.91 (14) and 20.96 (15)° with the furan ring. The dihedral angle between the two benzene rings is 46.89 (13)°. One ethyl group of one ethoxycarbonyl unit is disordered over two sets of sites with occupancies of 0.56 (12) and 0.44 (12). In the crystal, weak intramolecular C—H⋯O hydrogen bonds link the molecules into chains along the c axis.

Related literature

For background to the applications of furan-3,4-dicarboxylic acid and its esters, see: Deshpande et al. (2002 ▶). For related structures, see: Hu & Wu (2005 ▶) Hu et al. (2005 ▶). For the synthesis, see: Wu et al. (1997 ▶).

Experimental

Crystal data

C₂₂H₂₀O₅
M _r = 364.38
Orthorhombic,
a = 11.9535 (8) Å
b = 17.0116 (12) Å
c = 18.9219 (14) Å
V = 3847.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.965, T _max = 0.993
19957 measured reflections
3778 independent reflections
1952 reflections with I > 2σ(I)
R _int = 0.081

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.160
S = 1.01
3778 reflections
268 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536810045241/sj5048sup1.cif

e-66-o3116-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045241/sj5048Isup2.hkl

e-66-o3116-Isup2.hkl^{(185.3KB, 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
C4—H4⋯O3	0.93	2.56	3.453 (4)	161

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Acknowledgments

We are grateful to Hubei Normal University for financial support.

supplementary crystallographic information

Comment

Furan-3,4-dicarboxylic acid and its esters have been used as starting materials in the synthesis of several bioactive natural products and several pharmacologically useful molecules, preparation of complexes with rare earth metal ions and also as a potential dienes in Diels-Alder reactions for the synthesis of several novel heterocycles (Deshpande et al., 2002). The crystal structures of some furan-3,4-dicarboxylic acid diethyl esters have been reported previously (Hu & Wu, 2005; Hu et al., 2005). In this paper, we report the crystal structure of the title compound, (I). In compound (I), the C1–C6 and C11–C16 phenyl rings form dihedral angles of 54.91 (14) and 20.96 (15)°, respectively with the furan ring, Fig 1. The dihedral angle between the two benzene rings is 46.89 (13)°. In the crystal structure, weak intramolecular C4—H4···O3 hydrogen bonds link the molecules into chains along the c axis (Table 1 and Fig. 2).

Experimental

Compound (I) was synthesized according to the literature procedure (Wu et al., 1997). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution at room temperature.