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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3116.
Published online 2010 November 10. doi:  10.1107/S1600536810045241
PMCID: PMC3011628

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

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 [triangle]). For related structures, see: Hu & Wu (2005 [triangle]) Hu et al. (2005 [triangle]). For the synthesis, see: Wu et al. (1997 [triangle]).

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Object name is e-66-o3116-scheme1.jpg

Experimental

Crystal data

  • C22H20O5
  • M r = 364.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3116-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045241/sj5048sup1.cif

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

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

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.

Refinement

The C21/C22 ethyl group of an ethyl carboxylate unit is disordered over two positions with occupancies 0.56 (12)/0.44 (12). Suitable restraints were applied to the O—C and C—C distances involving the disordered atoms. The H atoms were placed in idealized positions and constrained to ride on their parent atoms,with C—H distances in the range 0.97–0.97 Å, and with Uiso(H) =1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for others. Each methyl group was allowed to rotate freely about its C—C bond.

Figures

Fig. 1.
View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The molecular packing of (I), viewed along the a axis.

Crystal data

C22H20O5F(000) = 1536
Mr = 364.38Dx = 1.258 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1354 reflections
a = 11.9535 (8) Åθ = 2.3–16.5°
b = 17.0116 (12) ŵ = 0.09 mm1
c = 18.9219 (14) ÅT = 293 K
V = 3847.7 (5) Å3Block, colorless
Z = 80.40 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer3778 independent reflections
Radiation source: fine-focus sealed tube1952 reflections with I > 2σ(I)
graphiteRint = 0.081
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −14→14
Tmin = 0.965, Tmax = 0.993k = −18→20
19957 measured reflectionsl = −23→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.160w = 1/[σ2(Fo2) + (0.0624P)2 + 0.4808P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3778 reflectionsΔρmax = 0.25 e Å3
268 parametersΔρmin = −0.27 e Å3
6 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0010 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C10.8016 (2)0.14397 (15)0.62303 (14)0.0490 (7)
C20.8864 (3)0.17700 (17)0.58313 (15)0.0605 (8)
H20.95790.18170.60210.073*
C30.8659 (4)0.2028 (2)0.51602 (17)0.0791 (10)
H30.92340.22520.48980.095*
C40.7618 (4)0.1959 (2)0.48719 (18)0.0840 (11)
H40.74830.21410.44170.101*
C50.6774 (3)0.1621 (2)0.52514 (18)0.0820 (11)
H50.60670.15690.50510.098*
C60.6963 (3)0.13579 (18)0.59302 (16)0.0665 (9)
H60.63870.11260.61860.080*
C70.8238 (2)0.11805 (15)0.69580 (14)0.0492 (7)
C80.7797 (2)0.13356 (15)0.76053 (14)0.0482 (7)
C90.8438 (2)0.08957 (16)0.81084 (14)0.0502 (7)
C100.9221 (2)0.04934 (16)0.77404 (14)0.0523 (7)
C111.0088 (2)−0.00776 (16)0.79305 (15)0.0527 (7)
C121.0976 (3)−0.02123 (18)0.74782 (17)0.0644 (8)
H121.10250.00580.70520.077*
C131.1795 (3)−0.0752 (2)0.7664 (2)0.0765 (10)
H131.2394−0.08410.73610.092*
C141.1728 (3)−0.1154 (2)0.8287 (2)0.0823 (11)
H141.2277−0.15190.84040.099*
C151.0860 (3)−0.10230 (19)0.87366 (19)0.0791 (10)
H151.0820−0.12950.91620.095*
C161.0039 (3)−0.04870 (17)0.85632 (16)0.0664 (9)
H160.9449−0.03990.88730.080*
C170.6899 (2)0.18876 (18)0.77946 (16)0.0570 (8)
C180.5443 (3)0.27088 (19)0.73529 (17)0.0713 (9)
H18A0.57070.31810.75870.086*
H18B0.48720.24680.76450.086*
C190.4984 (3)0.2902 (2)0.66417 (18)0.0901 (11)
H19A0.55390.31790.63720.135*
H19B0.43320.32270.66940.135*
H19C0.47850.24260.64010.135*
C200.8287 (3)0.08891 (18)0.88887 (16)0.0598 (8)
O10.91184 (16)0.06707 (10)0.70331 (9)0.0542 (5)
O20.63606 (18)0.21673 (12)0.72406 (10)0.0703 (6)
O30.66800 (19)0.20603 (17)0.83882 (12)0.1034 (9)
O40.7383 (2)0.04851 (17)0.90669 (11)0.1010 (9)
O50.89136 (19)0.11776 (13)0.93023 (11)0.0773 (7)
C220.6437 (8)0.0896 (6)1.0062 (4)0.108 (3)0.56
H22A0.68580.13761.00730.163*0.56
H22B0.61790.07741.05300.163*0.56
H22C0.58060.09560.97530.163*0.56
C210.7149 (11)0.0258 (6)0.9805 (5)0.088 (4)0.56
H21A0.6762−0.02430.98260.106*0.56
H21B0.78340.02231.00780.106*0.56
C21'0.7110 (15)0.0659 (11)0.9813 (5)0.107 (6)0.44
H21C0.70150.12200.98820.128*0.44
H21D0.77000.04751.01230.128*0.44
C22'0.6045 (8)0.0235 (7)0.9961 (5)0.116 (4)0.44
H22D0.54450.04790.97050.173*0.44
H22E0.58880.02551.04580.173*0.44
H22F0.6115−0.03040.98150.173*0.44

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0605 (18)0.0467 (16)0.0398 (16)0.0013 (14)0.0019 (14)−0.0015 (13)
C20.072 (2)0.0598 (19)0.0498 (19)−0.0033 (16)0.0079 (16)0.0032 (15)
C30.106 (3)0.078 (2)0.053 (2)−0.002 (2)0.013 (2)0.0133 (17)
C40.124 (3)0.081 (3)0.047 (2)0.024 (2)−0.003 (2)0.0108 (18)
C50.088 (3)0.105 (3)0.053 (2)0.015 (2)−0.012 (2)−0.006 (2)
C60.068 (2)0.083 (2)0.0479 (19)−0.0009 (17)0.0025 (16)−0.0035 (17)
C70.0581 (18)0.0435 (16)0.0458 (18)−0.0024 (14)−0.0003 (14)0.0012 (13)
C80.0561 (18)0.0496 (17)0.0389 (16)−0.0037 (14)0.0023 (14)0.0003 (13)
C90.0573 (17)0.0552 (17)0.0380 (16)−0.0107 (15)−0.0010 (14)0.0001 (13)
C100.0598 (19)0.0561 (19)0.0411 (17)−0.0076 (16)−0.0020 (15)0.0014 (14)
C110.0583 (19)0.0511 (17)0.0486 (18)−0.0080 (15)−0.0070 (15)−0.0027 (14)
C120.065 (2)0.059 (2)0.069 (2)−0.0058 (17)−0.0023 (18)0.0043 (16)
C130.063 (2)0.073 (2)0.093 (3)−0.0019 (19)−0.0025 (19)−0.004 (2)
C140.077 (3)0.070 (2)0.100 (3)0.0083 (19)−0.024 (2)0.002 (2)
C150.093 (3)0.075 (2)0.069 (2)0.011 (2)−0.018 (2)0.0121 (18)
C160.078 (2)0.064 (2)0.057 (2)0.0032 (18)−0.0064 (17)0.0031 (16)
C170.062 (2)0.070 (2)0.0397 (18)−0.0095 (16)−0.0018 (15)−0.0039 (15)
C180.068 (2)0.074 (2)0.072 (2)0.0157 (18)0.0038 (18)−0.0095 (17)
C190.099 (3)0.096 (3)0.075 (3)0.025 (2)−0.011 (2)0.002 (2)
C200.064 (2)0.070 (2)0.0456 (19)−0.0010 (17)−0.0030 (17)0.0004 (15)
O10.0654 (13)0.0538 (12)0.0434 (12)0.0046 (10)0.0026 (9)0.0025 (9)
O20.0822 (15)0.0820 (15)0.0465 (13)0.0269 (12)0.0012 (11)−0.0039 (11)
O30.0985 (18)0.164 (3)0.0481 (15)0.0494 (17)−0.0063 (13)−0.0242 (15)
O40.0833 (17)0.174 (3)0.0456 (14)−0.0452 (18)0.0023 (12)0.0138 (15)
O50.0858 (16)0.0948 (17)0.0513 (14)−0.0113 (13)−0.0116 (12)−0.0124 (12)
C220.122 (8)0.127 (8)0.076 (6)0.025 (6)0.022 (5)0.004 (5)
C210.081 (7)0.103 (9)0.081 (7)−0.008 (5)0.003 (5)0.018 (5)
C21'0.121 (12)0.162 (17)0.036 (6)−0.034 (12)0.029 (6)−0.015 (8)
C22'0.119 (9)0.105 (9)0.123 (9)−0.006 (7)0.049 (7)0.033 (7)

Geometric parameters (Å, °)

C1—C21.384 (4)C15—C161.379 (4)
C1—C61.387 (4)C15—H150.9300
C1—C71.470 (4)C16—H160.9300
C2—C31.366 (4)C17—O31.190 (3)
C2—H20.9300C17—O21.319 (3)
C3—C41.364 (5)C18—O21.448 (3)
C3—H30.9300C18—C191.491 (4)
C4—C51.365 (5)C18—H18A0.9700
C4—H40.9300C18—H18B0.9700
C5—C61.379 (4)C19—H19A0.9600
C5—H50.9300C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C81.359 (3)C20—O51.189 (3)
C7—O11.371 (3)C20—O41.324 (4)
C8—C91.433 (4)O4—C211.475 (8)
C8—C171.470 (4)O4—C21'1.479 (8)
C9—C101.353 (4)C22—C211.462 (9)
C9—C201.487 (4)C22—H22A0.9600
C10—O11.378 (3)C22—H22B0.9600
C10—C111.465 (4)C22—H22C0.9600
C11—C121.383 (4)C21—H21A0.9700
C11—C161.386 (4)C21—H21B0.9700
C12—C131.387 (4)C21'—C22'1.490 (10)
C12—H120.9300C21'—H21C0.9700
C13—C141.365 (5)C21'—H21D0.9700
C13—H130.9300C22'—H22D0.9600
C14—C151.360 (5)C22'—H22E0.9600
C14—H140.9300C22'—H22F0.9600
C2—C1—C6118.8 (3)C15—C16—C11120.5 (3)
C2—C1—C7120.0 (3)C15—C16—H16119.7
C6—C1—C7121.2 (3)C11—C16—H16119.7
C3—C2—C1120.4 (3)O3—C17—O2123.6 (3)
C3—C2—H2119.8O3—C17—C8123.2 (3)
C1—C2—H2119.8O2—C17—C8113.1 (2)
C4—C3—C2120.5 (3)O2—C18—C19106.7 (3)
C4—C3—H3119.7O2—C18—H18A110.4
C2—C3—H3119.7C19—C18—H18A110.4
C3—C4—C5120.0 (3)O2—C18—H18B110.4
C3—C4—H4120.0C19—C18—H18B110.4
C5—C4—H4120.0H18A—C18—H18B108.6
C4—C5—C6120.4 (3)C18—C19—H19A109.5
C4—C5—H5119.8C18—C19—H19B109.5
C6—C5—H5119.8H19A—C19—H19B109.5
C5—C6—C1119.8 (3)C18—C19—H19C109.5
C5—C6—H6120.1H19A—C19—H19C109.5
C1—C6—H6120.1H19B—C19—H19C109.5
C8—C7—O1109.1 (2)O5—C20—O4124.1 (3)
C8—C7—C1135.7 (3)O5—C20—C9125.0 (3)
O1—C7—C1115.2 (2)O4—C20—C9110.8 (3)
C7—C8—C9106.8 (2)C7—O1—C10107.9 (2)
C7—C8—C17128.8 (3)C17—O2—C18118.8 (2)
C9—C8—C17124.2 (2)C20—O4—C21122.1 (6)
C10—C9—C8107.0 (2)C20—O4—C21'108.6 (5)
C10—C9—C20126.2 (3)C21—O4—C21'26.8 (8)
C8—C9—C20126.8 (3)C22—C21—O4103.4 (7)
C9—C10—O1109.1 (2)C22—C21—H21A111.1
C9—C10—C11134.3 (3)O4—C21—H21A111.1
O1—C10—C11116.5 (2)C22—C21—H21B111.1
C12—C11—C16118.9 (3)O4—C21—H21B111.1
C12—C11—C10120.1 (3)H21A—C21—H21B109.1
C16—C11—C10121.0 (3)O4—C21'—C22'105.7 (8)
C11—C12—C13119.7 (3)O4—C21'—H21C110.6
C11—C12—H12120.2C22'—C21'—H21C110.6
C13—C12—H12120.2O4—C21'—H21D110.6
C14—C13—C12120.6 (3)C22'—C21'—H21D110.6
C14—C13—H13119.7H21C—C21'—H21D108.7
C12—C13—H13119.7C21'—C22'—H22D109.5
C15—C14—C13120.2 (3)C21'—C22'—H22E109.5
C15—C14—H14119.9H22D—C22'—H22E109.5
C13—C14—H14119.9C21'—C22'—H22F109.5
C14—C15—C16120.1 (3)H22D—C22'—H22F109.5
C14—C15—H15119.9H22E—C22'—H22F109.5
C16—C15—H15119.9
C6—C1—C2—C31.6 (4)C11—C12—C13—C140.3 (5)
C7—C1—C2—C3−178.6 (3)C12—C13—C14—C15−0.6 (5)
C1—C2—C3—C4−0.4 (5)C13—C14—C15—C160.5 (5)
C2—C3—C4—C5−0.8 (5)C14—C15—C16—C110.0 (5)
C3—C4—C5—C60.8 (5)C12—C11—C16—C15−0.4 (4)
C4—C5—C6—C10.4 (5)C10—C11—C16—C15180.0 (3)
C2—C1—C6—C5−1.5 (4)C7—C8—C17—O3−169.1 (3)
C7—C1—C6—C5178.7 (3)C9—C8—C17—O35.6 (5)
C2—C1—C7—C8124.2 (4)C7—C8—C17—O211.2 (4)
C6—C1—C7—C8−56.0 (5)C9—C8—C17—O2−174.0 (2)
C2—C1—C7—O1−53.9 (3)C10—C9—C20—O569.8 (4)
C6—C1—C7—O1125.9 (3)C8—C9—C20—O5−109.1 (4)
O1—C7—C8—C9−0.1 (3)C10—C9—C20—O4−107.2 (3)
C1—C7—C8—C9−178.2 (3)C8—C9—C20—O473.8 (4)
O1—C7—C8—C17175.3 (2)C8—C7—O1—C100.9 (3)
C1—C7—C8—C17−2.8 (5)C1—C7—O1—C10179.4 (2)
C7—C8—C9—C10−0.6 (3)C9—C10—O1—C7−1.3 (3)
C17—C8—C9—C10−176.3 (2)C11—C10—O1—C7177.2 (2)
C7—C8—C9—C20178.5 (3)O3—C17—O2—C18−0.6 (5)
C17—C8—C9—C202.8 (4)C8—C17—O2—C18179.0 (2)
C8—C9—C10—O11.2 (3)C19—C18—O2—C17−178.4 (3)
C20—C9—C10—O1−178.0 (3)O5—C20—O4—C21−8.8 (6)
C8—C9—C10—C11−176.9 (3)C9—C20—O4—C21168.3 (5)
C20—C9—C10—C114.0 (5)O5—C20—O4—C21'17.0 (11)
C9—C10—C11—C12−160.6 (3)C9—C20—O4—C21'−166.0 (10)
O1—C10—C11—C1221.5 (4)C20—O4—C21—C2293.6 (10)
C9—C10—C11—C1619.1 (5)C21'—O4—C21—C2227.6 (18)
O1—C10—C11—C16−158.9 (3)C20—O4—C21'—C22'175.9 (12)
C16—C11—C12—C130.2 (4)C21—O4—C21'—C22'−58.8 (17)
C10—C11—C12—C13179.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O3i0.932.563.453 (4)161

Symmetry codes: (i) .

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5048).

References

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