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In the title compound, C18H16O3, the dihedral angles between the two benzene rings and the furan ring are 3.7 (1) and 1.0 (1)°. C—H...π and π–π inter­actions are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027911/ww6423sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027911/ww6423Isup2.hkl
Contains datablock I

CCDC reference: 287756

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.053
  • wR factor = 0.139
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. CG2 .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A .. CG3 .. 3.24 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C18 .. CG3 .. 4.09 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

We have synthesized 2,5-bis(2-methoxyphenyl)furan, (I), according to the literature method of Wu et al. (1997) and its structure is reported here.

The molecule is essentially planar (Fig. 1). Selected bond lengths and angles are listed in Table 1. Some C—H···π and ππ interactions are observed in the crystal structure (see Table 2 and Fig. 2). Analysis using PLATON (Spek, 2003) shows that the distance between the centroids of the C2–C7 and C12i–C17i benzene rings is 3.89 (1) Å [symmetry code: (i) x, 1 + y, z].

Experimental top

3-Ethoxy-1-(2-methoxyphenyl)propan-1-one was first synthesized according to the literature (Pelter et al., 1982). Sodium hydride (0.4 g, 80%) was washed with dry pentane and then suspended in dry CH2Cl2 (10 ml). To this was added a solution of ethyl 3-(2-methoxyphenyl)-3-oxopropanoate (2.2 g, 10 mmol) in dry CH2Cl2 (15 ml) and then a solution of ethyl 2-bromo-3-(2-methoxyphenyl)-3-oxopropanoate (3 g, 10 mmol) in dry CH2Cl2 was added. The product was then refluxed with stirring for 3 h. The suspension was cooled, washed with water (20 ml), and dried (Na2SO4). After removal of the solvent, the residue was purified and affording diethyl 2,3-bis(2-methoxybenzoyl)succinate. Toluene-p-sulfonic acid (5 g) was added to a solution of compound diethyl 2,3-bis(2-methoxybenzoyl)succinate (2.2 g, 5 mmol) in dry benzene (50 ml). The mixture was refluxed for 8 h and concentrated. The residue was chromatographed on silica gel (light petroleum–ethyl acetate, 8:1 (v/v) to give diethyl 2,5-bis(2-methoxyphenyl)furan-3,4-dicarboxylate which was hydrogenated, oxidized and decarboxylated to give the title compound. Crystals suitable for X-ray analysis were obtained by recrystallization of the the title compound from ethanol over a period of two weeks.

Refinement top

All H atoms were placed at idealized positions (methyl C—H = 0.96 Å, methylene C—H = 0.97 Å and aromatic C—H = 0.93 Å) and included in the refinement in the riding-motion approximation, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) for all other H atoms. Cg1, Cg2 and Cg3 are the centroids of rings C12–C17, C2–C7 and O3/C8–C11, respectively.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing diagram of (I), showing the C—H–π and ππ interactions as dashed lines. [Symmetry codes: (a) x, 1 + y, z; (b) x, 1 − y, −1/2 + z; (c) x, −y, 1/2 + z; (d) x, −1 + y, z.]
2,5-Bis(2-methoxyphenyl)furan top
Crystal data top
C18H16O3F(000) = 592
Mr = 280.31Dx = 1.312 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 1227 reflections
a = 15.4110 (18) Åθ = 2.8–23.2°
b = 6.6402 (8) ŵ = 0.09 mm1
c = 14.6523 (17) ÅT = 292 K
β = 108.898 (2)°Block, yellow
V = 1418.6 (3) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3106 independent reflections
Radiation source: fine-focus sealed tube1899 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1919
Tmin = 0.976, Tmax = 0.984k = 88
8057 measured reflectionsl = 1418
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.0627P]
where P = (Fo2 + 2Fc2)/3
3106 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C18H16O3V = 1418.6 (3) Å3
Mr = 280.31Z = 4
Monoclinic, P2/cMo Kα radiation
a = 15.4110 (18) ŵ = 0.09 mm1
b = 6.6402 (8) ÅT = 292 K
c = 14.6523 (17) Å0.30 × 0.30 × 0.20 mm
β = 108.898 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3106 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
1899 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.984Rint = 0.037
8057 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.03Δρmax = 0.18 e Å3
3106 reflectionsΔρmin = 0.15 e Å3
192 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.06213 (16)0.8280 (3)0.17302 (16)0.0691 (7)
H1A0.06810.95830.20280.104*
H1B0.00090.78640.15360.104*
H1C0.08210.83480.11740.104*
C20.21033 (14)0.7087 (3)0.26713 (13)0.0455 (5)
C30.25280 (16)0.8638 (3)0.23532 (15)0.0591 (6)
H30.21750.96180.19460.071*
C40.34688 (17)0.8748 (3)0.26344 (16)0.0643 (6)
H40.37470.97930.24100.077*
C50.40005 (16)0.7325 (3)0.32435 (16)0.0600 (6)
H50.46370.74000.34310.072*
C60.35777 (14)0.5775 (3)0.35761 (14)0.0518 (5)
H60.39380.48210.39940.062*
C70.26305 (13)0.5614 (3)0.33006 (12)0.0420 (4)
C80.22105 (13)0.3957 (3)0.36622 (12)0.0424 (5)
C90.13535 (14)0.3385 (3)0.36026 (15)0.0502 (5)
H90.08120.40420.32640.060*
C100.14314 (13)0.1607 (3)0.41493 (14)0.0494 (5)
H100.09490.08790.42380.059*
C110.23290 (12)0.1150 (3)0.45203 (13)0.0409 (4)
C120.28806 (12)0.0448 (3)0.51193 (12)0.0407 (4)
C130.38313 (13)0.0420 (3)0.53593 (14)0.0512 (5)
H130.41060.06270.51310.061*
C140.43807 (15)0.1894 (3)0.59248 (15)0.0603 (6)
H140.50150.18360.60800.072*
C150.39731 (16)0.3446 (3)0.62538 (15)0.0629 (6)
H150.43360.44530.66300.075*
C160.30396 (15)0.3535 (3)0.60362 (14)0.0551 (6)
H160.27740.45980.62630.066*
C170.24914 (13)0.2045 (3)0.54791 (13)0.0443 (5)
C180.11381 (15)0.3485 (3)0.56670 (17)0.0671 (6)
H18A0.12390.47870.54350.101*
H18B0.04910.32350.54900.101*
H18C0.14050.34450.63570.101*
O10.11709 (9)0.6865 (2)0.23999 (10)0.0573 (4)
O20.15512 (9)0.19837 (19)0.52509 (10)0.0556 (4)
O30.28224 (8)0.25900 (18)0.42251 (9)0.0436 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0738 (16)0.0675 (15)0.0609 (14)0.0201 (12)0.0149 (12)0.0221 (12)
C20.0591 (13)0.0396 (11)0.0408 (11)0.0047 (9)0.0201 (9)0.0011 (9)
C30.0763 (17)0.0491 (13)0.0569 (14)0.0053 (11)0.0285 (12)0.0138 (10)
C40.0867 (18)0.0493 (13)0.0648 (15)0.0081 (12)0.0352 (13)0.0087 (11)
C50.0629 (14)0.0559 (13)0.0655 (14)0.0083 (11)0.0267 (12)0.0010 (11)
C60.0614 (14)0.0430 (11)0.0507 (12)0.0003 (10)0.0180 (10)0.0013 (9)
C70.0545 (12)0.0358 (10)0.0381 (10)0.0005 (9)0.0182 (9)0.0023 (8)
C80.0532 (12)0.0376 (10)0.0347 (10)0.0028 (9)0.0118 (8)0.0014 (8)
C90.0466 (12)0.0464 (12)0.0535 (12)0.0018 (9)0.0106 (9)0.0075 (9)
C100.0469 (12)0.0457 (12)0.0528 (12)0.0063 (9)0.0125 (9)0.0053 (9)
C110.0488 (12)0.0367 (10)0.0374 (10)0.0067 (8)0.0144 (8)0.0012 (8)
C120.0500 (12)0.0378 (10)0.0343 (10)0.0015 (8)0.0137 (8)0.0010 (8)
C130.0563 (13)0.0509 (12)0.0480 (12)0.0024 (10)0.0190 (10)0.0047 (9)
C140.0581 (14)0.0661 (15)0.0571 (13)0.0127 (11)0.0191 (11)0.0101 (11)
C150.0735 (16)0.0599 (14)0.0544 (14)0.0214 (12)0.0195 (12)0.0160 (11)
C160.0729 (16)0.0426 (12)0.0504 (12)0.0029 (10)0.0210 (11)0.0098 (9)
C170.0545 (13)0.0417 (11)0.0369 (10)0.0020 (9)0.0151 (9)0.0018 (9)
C180.0724 (16)0.0582 (14)0.0751 (16)0.0172 (12)0.0299 (13)0.0103 (12)
O10.0593 (10)0.0541 (9)0.0572 (9)0.0111 (7)0.0171 (7)0.0168 (7)
O20.0574 (9)0.0503 (8)0.0581 (9)0.0089 (7)0.0172 (7)0.0118 (7)
O30.0483 (8)0.0380 (7)0.0443 (7)0.0005 (6)0.0148 (6)0.0050 (6)
Geometric parameters (Å, º) top
C1—O11.423 (2)C10—C111.347 (2)
C1—H1A0.9600C10—H100.9300
C1—H1B0.9600C11—O31.376 (2)
C1—H1C0.9600C11—C121.461 (2)
C2—O11.369 (2)C12—C131.392 (2)
C2—C31.380 (3)C12—C171.402 (2)
C2—C71.407 (3)C13—C141.381 (3)
C3—C41.375 (3)C13—H130.9300
C3—H30.9300C14—C151.373 (3)
C4—C51.373 (3)C14—H140.9300
C4—H40.9300C15—C161.370 (3)
C5—C61.388 (3)C15—H150.9300
C5—H50.9300C16—C171.383 (3)
C6—C71.387 (2)C16—H160.9300
C6—H60.9300C17—O21.378 (2)
C7—C81.460 (2)C18—O21.422 (2)
C8—C91.350 (2)C18—H18A0.9600
C8—O31.375 (2)C18—H18B0.9600
C9—C101.410 (3)C18—H18C0.9600
C9—H90.9300
O1—C1—H1A109.5C9—C10—H10126.1
O1—C1—H1B109.5C10—C11—O3108.44 (16)
H1A—C1—H1B109.5C10—C11—C12136.69 (17)
O1—C1—H1C109.5O3—C11—C12114.86 (15)
H1A—C1—H1C109.5C13—C12—C17117.32 (17)
H1B—C1—H1C109.5C13—C12—C11120.11 (16)
O1—C2—C3123.38 (18)C17—C12—C11122.57 (17)
O1—C2—C7116.38 (16)C14—C13—C12122.18 (19)
C3—C2—C7120.24 (19)C14—C13—H13118.9
C4—C3—C2120.5 (2)C12—C13—H13118.9
C4—C3—H3119.7C15—C14—C13118.8 (2)
C2—C3—H3119.7C15—C14—H14120.6
C5—C4—C3120.5 (2)C13—C14—H14120.6
C5—C4—H4119.7C16—C15—C14121.0 (2)
C3—C4—H4119.7C16—C15—H15119.5
C4—C5—C6119.3 (2)C14—C15—H15119.5
C4—C5—H5120.4C15—C16—C17120.09 (19)
C6—C5—H5120.4C15—C16—H16120.0
C7—C6—C5121.62 (19)C17—C16—H16120.0
C7—C6—H6119.2O2—C17—C16123.90 (17)
C5—C6—H6119.2O2—C17—C12115.51 (16)
C6—C7—C2117.85 (17)C16—C17—C12120.58 (18)
C6—C7—C8120.05 (17)O2—C18—H18A109.5
C2—C7—C8122.10 (18)O2—C18—H18B109.5
C9—C8—O3108.63 (16)H18A—C18—H18B109.5
C9—C8—C7136.74 (18)O2—C18—H18C109.5
O3—C8—C7114.63 (16)H18A—C18—H18C109.5
C8—C9—C10107.32 (17)H18B—C18—H18C109.5
C8—C9—H9126.3C2—O1—C1117.61 (16)
C10—C9—H9126.3C17—O2—C18117.19 (15)
C11—C10—C9107.78 (16)C8—O3—C11107.83 (14)
C11—C10—H10126.1
O1—C2—C3—C4178.37 (18)C10—C11—C12—C170.9 (3)
C7—C2—C3—C41.0 (3)O3—C11—C12—C17179.62 (15)
C2—C3—C4—C50.6 (3)C17—C12—C13—C140.2 (3)
C3—C4—C5—C60.2 (3)C11—C12—C13—C14179.86 (18)
C4—C5—C6—C70.7 (3)C12—C13—C14—C150.5 (3)
C5—C6—C7—C20.3 (3)C13—C14—C15—C160.6 (3)
C5—C6—C7—C8179.73 (17)C14—C15—C16—C170.2 (3)
O1—C2—C7—C6178.88 (15)C15—C16—C17—O2177.94 (17)
C3—C2—C7—C60.6 (3)C15—C16—C17—C121.0 (3)
O1—C2—C7—C81.1 (3)C13—C12—C17—O2178.01 (15)
C3—C2—C7—C8179.43 (16)C11—C12—C17—O21.6 (2)
C6—C7—C8—C9175.5 (2)C13—C12—C17—C161.0 (3)
C2—C7—C8—C94.5 (3)C11—C12—C17—C16179.41 (17)
C6—C7—C8—O33.6 (2)C3—C2—O1—C12.1 (3)
C2—C7—C8—O3176.47 (15)C7—C2—O1—C1177.27 (17)
O3—C8—C9—C100.3 (2)C16—C17—O2—C183.9 (3)
C7—C8—C9—C10178.9 (2)C12—C17—O2—C18175.02 (16)
C8—C9—C10—C110.2 (2)C9—C8—O3—C110.21 (19)
C9—C10—C11—O30.1 (2)C7—C8—O3—C11179.12 (14)
C9—C10—C11—C12178.7 (2)C10—C11—O3—C80.07 (19)
C10—C11—C12—C13179.5 (2)C12—C11—O3—C8179.15 (14)
O3—C11—C12—C130.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···Cg1i0.932.803.541 (1)137
C16—H16···Cg2ii0.932.953.722 (1)142
C18—H18A···Cg3iii0.963.244.091 (1)149
Symmetry codes: (i) x, y+1, z3/2; (ii) x, y, z1/2; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC18H16O3
Mr280.31
Crystal system, space groupMonoclinic, P2/c
Temperature (K)292
a, b, c (Å)15.4110 (18), 6.6402 (8), 14.6523 (17)
β (°) 108.898 (2)
V3)1418.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.976, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
8057, 3106, 1899
Rint0.037
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.139, 1.03
No. of reflections3106
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top
C1—O11.423 (2)C11—O31.376 (2)
C2—O11.369 (2)C12—C131.392 (2)
C2—C71.407 (3)C12—C171.402 (2)
C6—C71.387 (2)C17—O21.378 (2)
C7—C81.460 (2)C18—O21.422 (2)
C2—C7—C8122.10 (18)O3—C11—C12114.86 (15)
C9—C8—C7136.74 (18)O2—C17—C12115.51 (16)
O3—C8—C7114.63 (16)C2—O1—C1117.61 (16)
C10—C11—C12136.69 (17)C8—O3—C11107.83 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···Cg1i0.932.803.541 (1)137
C16—H16···Cg2ii0.932.953.722 (1)142
C18—H18A···Cg3iii0.963.244.091 (1)149
Symmetry codes: (i) x, y+1, z3/2; (ii) x, y, z1/2; (iii) x, y1, z.
 

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