Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027911/ww6423sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027911/ww6423Isup2.hkl |
CCDC reference: 287756
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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.
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.
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.
C18H16O3 | F(000) = 592 |
Mr = 280.31 | Dx = 1.312 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 1227 reflections |
a = 15.4110 (18) Å | θ = 2.8–23.2° |
b = 6.6402 (8) Å | µ = 0.09 mm−1 |
c = 14.6523 (17) Å | T = 292 K |
β = 108.898 (2)° | Block, yellow |
V = 1418.6 (3) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3106 independent reflections |
Radiation source: fine-focus sealed tube | 1899 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 27.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −19→19 |
Tmin = 0.976, Tmax = 0.984 | k = −8→8 |
8057 measured reflections | l = −14→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-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 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C18H16O3 | V = 1418.6 (3) Å3 |
Mr = 280.31 | Z = 4 |
Monoclinic, P2/c | Mo Kα radiation |
a = 15.4110 (18) Å | µ = 0.09 mm−1 |
b = 6.6402 (8) Å | T = 292 K |
c = 14.6523 (17) Å | 0.30 × 0.30 × 0.20 mm |
β = 108.898 (2)° |
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 = 0.984 | Rint = 0.037 |
8057 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.18 e Å−3 |
3106 reflections | Δρmin = −0.15 e Å−3 |
192 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.06213 (16) | 0.8280 (3) | 0.17302 (16) | 0.0691 (7) | |
H1A | 0.0681 | 0.9583 | 0.2028 | 0.104* | |
H1B | −0.0009 | 0.7864 | 0.1536 | 0.104* | |
H1C | 0.0821 | 0.8348 | 0.1174 | 0.104* | |
C2 | 0.21033 (14) | 0.7087 (3) | 0.26713 (13) | 0.0455 (5) | |
C3 | 0.25280 (16) | 0.8638 (3) | 0.23532 (15) | 0.0591 (6) | |
H3 | 0.2175 | 0.9618 | 0.1946 | 0.071* | |
C4 | 0.34688 (17) | 0.8748 (3) | 0.26344 (16) | 0.0643 (6) | |
H4 | 0.3747 | 0.9793 | 0.2410 | 0.077* | |
C5 | 0.40005 (16) | 0.7325 (3) | 0.32435 (16) | 0.0600 (6) | |
H5 | 0.4637 | 0.7400 | 0.3431 | 0.072* | |
C6 | 0.35777 (14) | 0.5775 (3) | 0.35761 (14) | 0.0518 (5) | |
H6 | 0.3938 | 0.4821 | 0.3994 | 0.062* | |
C7 | 0.26305 (13) | 0.5614 (3) | 0.33006 (12) | 0.0420 (4) | |
C8 | 0.22105 (13) | 0.3957 (3) | 0.36622 (12) | 0.0424 (5) | |
C9 | 0.13535 (14) | 0.3385 (3) | 0.36026 (15) | 0.0502 (5) | |
H9 | 0.0812 | 0.4042 | 0.3264 | 0.060* | |
C10 | 0.14314 (13) | 0.1607 (3) | 0.41493 (14) | 0.0494 (5) | |
H10 | 0.0949 | 0.0879 | 0.4238 | 0.059* | |
C11 | 0.23290 (12) | 0.1150 (3) | 0.45203 (13) | 0.0409 (4) | |
C12 | 0.28806 (12) | −0.0448 (3) | 0.51193 (12) | 0.0407 (4) | |
C13 | 0.38313 (13) | −0.0420 (3) | 0.53593 (14) | 0.0512 (5) | |
H13 | 0.4106 | 0.0627 | 0.5131 | 0.061* | |
C14 | 0.43807 (15) | −0.1894 (3) | 0.59248 (15) | 0.0603 (6) | |
H14 | 0.5015 | −0.1836 | 0.6080 | 0.072* | |
C15 | 0.39731 (16) | −0.3446 (3) | 0.62538 (15) | 0.0629 (6) | |
H15 | 0.4336 | −0.4453 | 0.6630 | 0.075* | |
C16 | 0.30396 (15) | −0.3535 (3) | 0.60362 (14) | 0.0551 (6) | |
H16 | 0.2774 | −0.4598 | 0.6263 | 0.066* | |
C17 | 0.24914 (13) | −0.2045 (3) | 0.54791 (13) | 0.0443 (5) | |
C18 | 0.11381 (15) | −0.3485 (3) | 0.56670 (17) | 0.0671 (6) | |
H18A | 0.1239 | −0.4787 | 0.5435 | 0.101* | |
H18B | 0.0491 | −0.3235 | 0.5490 | 0.101* | |
H18C | 0.1405 | −0.3445 | 0.6357 | 0.101* | |
O1 | 0.11709 (9) | 0.6865 (2) | 0.23999 (10) | 0.0573 (4) | |
O2 | 0.15512 (9) | −0.19837 (19) | 0.52509 (10) | 0.0556 (4) | |
O3 | 0.28224 (8) | 0.25900 (18) | 0.42251 (9) | 0.0436 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0738 (16) | 0.0675 (15) | 0.0609 (14) | 0.0201 (12) | 0.0149 (12) | 0.0221 (12) |
C2 | 0.0591 (13) | 0.0396 (11) | 0.0408 (11) | 0.0047 (9) | 0.0201 (9) | 0.0011 (9) |
C3 | 0.0763 (17) | 0.0491 (13) | 0.0569 (14) | 0.0053 (11) | 0.0285 (12) | 0.0138 (10) |
C4 | 0.0867 (18) | 0.0493 (13) | 0.0648 (15) | −0.0081 (12) | 0.0352 (13) | 0.0087 (11) |
C5 | 0.0629 (14) | 0.0559 (13) | 0.0655 (14) | −0.0083 (11) | 0.0267 (12) | −0.0010 (11) |
C6 | 0.0614 (14) | 0.0430 (11) | 0.0507 (12) | 0.0003 (10) | 0.0180 (10) | 0.0013 (9) |
C7 | 0.0545 (12) | 0.0358 (10) | 0.0381 (10) | −0.0005 (9) | 0.0182 (9) | −0.0023 (8) |
C8 | 0.0532 (12) | 0.0376 (10) | 0.0347 (10) | 0.0028 (9) | 0.0118 (8) | 0.0014 (8) |
C9 | 0.0466 (12) | 0.0464 (12) | 0.0535 (12) | 0.0018 (9) | 0.0106 (9) | 0.0075 (9) |
C10 | 0.0469 (12) | 0.0457 (12) | 0.0528 (12) | −0.0063 (9) | 0.0125 (9) | 0.0053 (9) |
C11 | 0.0488 (12) | 0.0367 (10) | 0.0374 (10) | −0.0067 (8) | 0.0144 (8) | −0.0012 (8) |
C12 | 0.0500 (12) | 0.0378 (10) | 0.0343 (10) | −0.0015 (8) | 0.0137 (8) | −0.0010 (8) |
C13 | 0.0563 (13) | 0.0509 (12) | 0.0480 (12) | 0.0024 (10) | 0.0190 (10) | 0.0047 (9) |
C14 | 0.0581 (14) | 0.0661 (15) | 0.0571 (13) | 0.0127 (11) | 0.0191 (11) | 0.0101 (11) |
C15 | 0.0735 (16) | 0.0599 (14) | 0.0544 (14) | 0.0214 (12) | 0.0195 (12) | 0.0160 (11) |
C16 | 0.0729 (16) | 0.0426 (12) | 0.0504 (12) | 0.0029 (10) | 0.0210 (11) | 0.0098 (9) |
C17 | 0.0545 (13) | 0.0417 (11) | 0.0369 (10) | −0.0020 (9) | 0.0151 (9) | −0.0018 (9) |
C18 | 0.0724 (16) | 0.0582 (14) | 0.0751 (16) | −0.0172 (12) | 0.0299 (13) | 0.0103 (12) |
O1 | 0.0593 (10) | 0.0541 (9) | 0.0572 (9) | 0.0111 (7) | 0.0171 (7) | 0.0168 (7) |
O2 | 0.0574 (9) | 0.0503 (8) | 0.0581 (9) | −0.0089 (7) | 0.0172 (7) | 0.0118 (7) |
O3 | 0.0483 (8) | 0.0380 (7) | 0.0443 (7) | −0.0005 (6) | 0.0148 (6) | 0.0050 (6) |
C1—O1 | 1.423 (2) | C10—C11 | 1.347 (2) |
C1—H1A | 0.9600 | C10—H10 | 0.9300 |
C1—H1B | 0.9600 | C11—O3 | 1.376 (2) |
C1—H1C | 0.9600 | C11—C12 | 1.461 (2) |
C2—O1 | 1.369 (2) | C12—C13 | 1.392 (2) |
C2—C3 | 1.380 (3) | C12—C17 | 1.402 (2) |
C2—C7 | 1.407 (3) | C13—C14 | 1.381 (3) |
C3—C4 | 1.375 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.373 (3) |
C4—C5 | 1.373 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.370 (3) |
C5—C6 | 1.388 (3) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—C17 | 1.383 (3) |
C6—C7 | 1.387 (2) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—O2 | 1.378 (2) |
C7—C8 | 1.460 (2) | C18—O2 | 1.422 (2) |
C8—C9 | 1.350 (2) | C18—H18A | 0.9600 |
C8—O3 | 1.375 (2) | C18—H18B | 0.9600 |
C9—C10 | 1.410 (3) | C18—H18C | 0.9600 |
C9—H9 | 0.9300 | ||
O1—C1—H1A | 109.5 | C9—C10—H10 | 126.1 |
O1—C1—H1B | 109.5 | C10—C11—O3 | 108.44 (16) |
H1A—C1—H1B | 109.5 | C10—C11—C12 | 136.69 (17) |
O1—C1—H1C | 109.5 | O3—C11—C12 | 114.86 (15) |
H1A—C1—H1C | 109.5 | C13—C12—C17 | 117.32 (17) |
H1B—C1—H1C | 109.5 | C13—C12—C11 | 120.11 (16) |
O1—C2—C3 | 123.38 (18) | C17—C12—C11 | 122.57 (17) |
O1—C2—C7 | 116.38 (16) | C14—C13—C12 | 122.18 (19) |
C3—C2—C7 | 120.24 (19) | C14—C13—H13 | 118.9 |
C4—C3—C2 | 120.5 (2) | C12—C13—H13 | 118.9 |
C4—C3—H3 | 119.7 | C15—C14—C13 | 118.8 (2) |
C2—C3—H3 | 119.7 | C15—C14—H14 | 120.6 |
C5—C4—C3 | 120.5 (2) | C13—C14—H14 | 120.6 |
C5—C4—H4 | 119.7 | C16—C15—C14 | 121.0 (2) |
C3—C4—H4 | 119.7 | C16—C15—H15 | 119.5 |
C4—C5—C6 | 119.3 (2) | C14—C15—H15 | 119.5 |
C4—C5—H5 | 120.4 | C15—C16—C17 | 120.09 (19) |
C6—C5—H5 | 120.4 | C15—C16—H16 | 120.0 |
C7—C6—C5 | 121.62 (19) | C17—C16—H16 | 120.0 |
C7—C6—H6 | 119.2 | O2—C17—C16 | 123.90 (17) |
C5—C6—H6 | 119.2 | O2—C17—C12 | 115.51 (16) |
C6—C7—C2 | 117.85 (17) | C16—C17—C12 | 120.58 (18) |
C6—C7—C8 | 120.05 (17) | O2—C18—H18A | 109.5 |
C2—C7—C8 | 122.10 (18) | O2—C18—H18B | 109.5 |
C9—C8—O3 | 108.63 (16) | H18A—C18—H18B | 109.5 |
C9—C8—C7 | 136.74 (18) | O2—C18—H18C | 109.5 |
O3—C8—C7 | 114.63 (16) | H18A—C18—H18C | 109.5 |
C8—C9—C10 | 107.32 (17) | H18B—C18—H18C | 109.5 |
C8—C9—H9 | 126.3 | C2—O1—C1 | 117.61 (16) |
C10—C9—H9 | 126.3 | C17—O2—C18 | 117.19 (15) |
C11—C10—C9 | 107.78 (16) | C8—O3—C11 | 107.83 (14) |
C11—C10—H10 | 126.1 | ||
O1—C2—C3—C4 | −178.37 (18) | C10—C11—C12—C17 | −0.9 (3) |
C7—C2—C3—C4 | 1.0 (3) | O3—C11—C12—C17 | −179.62 (15) |
C2—C3—C4—C5 | −0.6 (3) | C17—C12—C13—C14 | 0.2 (3) |
C3—C4—C5—C6 | −0.2 (3) | C11—C12—C13—C14 | 179.86 (18) |
C4—C5—C6—C7 | 0.7 (3) | C12—C13—C14—C15 | 0.5 (3) |
C5—C6—C7—C2 | −0.3 (3) | C13—C14—C15—C16 | −0.6 (3) |
C5—C6—C7—C8 | 179.73 (17) | C14—C15—C16—C17 | −0.2 (3) |
O1—C2—C7—C6 | 178.88 (15) | C15—C16—C17—O2 | −177.94 (17) |
C3—C2—C7—C6 | −0.6 (3) | C15—C16—C17—C12 | 1.0 (3) |
O1—C2—C7—C8 | −1.1 (3) | C13—C12—C17—O2 | 178.01 (15) |
C3—C2—C7—C8 | 179.43 (16) | C11—C12—C17—O2 | −1.6 (2) |
C6—C7—C8—C9 | 175.5 (2) | C13—C12—C17—C16 | −1.0 (3) |
C2—C7—C8—C9 | −4.5 (3) | C11—C12—C17—C16 | 179.41 (17) |
C6—C7—C8—O3 | −3.6 (2) | C3—C2—O1—C1 | 2.1 (3) |
C2—C7—C8—O3 | 176.47 (15) | C7—C2—O1—C1 | −177.27 (17) |
O3—C8—C9—C10 | 0.3 (2) | C16—C17—O2—C18 | 3.9 (3) |
C7—C8—C9—C10 | −178.9 (2) | C12—C17—O2—C18 | −175.02 (16) |
C8—C9—C10—C11 | −0.2 (2) | C9—C8—O3—C11 | −0.21 (19) |
C9—C10—C11—O3 | 0.1 (2) | C7—C8—O3—C11 | 179.12 (14) |
C9—C10—C11—C12 | −178.7 (2) | C10—C11—O3—C8 | 0.07 (19) |
C10—C11—C12—C13 | 179.5 (2) | C12—C11—O3—C8 | 179.15 (14) |
O3—C11—C12—C13 | 0.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg1i | 0.93 | 2.80 | 3.541 (1) | 137 |
C16—H16···Cg2ii | 0.93 | 2.95 | 3.722 (1) | 142 |
C18—H18A···Cg3iii | 0.96 | 3.24 | 4.091 (1) | 149 |
Symmetry codes: (i) x, −y+1, z−3/2; (ii) x, −y, z−1/2; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H16O3 |
Mr | 280.31 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 292 |
a, b, c (Å) | 15.4110 (18), 6.6402 (8), 14.6523 (17) |
β (°) | 108.898 (2) |
V (Å3) | 1418.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.976, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8057, 3106, 1899 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.139, 1.03 |
No. of reflections | 3106 |
No. of parameters | 192 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.15 |
Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
C1—O1 | 1.423 (2) | C11—O3 | 1.376 (2) |
C2—O1 | 1.369 (2) | C12—C13 | 1.392 (2) |
C2—C7 | 1.407 (3) | C12—C17 | 1.402 (2) |
C6—C7 | 1.387 (2) | C17—O2 | 1.378 (2) |
C7—C8 | 1.460 (2) | C18—O2 | 1.422 (2) |
C2—C7—C8 | 122.10 (18) | O3—C11—C12 | 114.86 (15) |
C9—C8—C7 | 136.74 (18) | O2—C17—C12 | 115.51 (16) |
O3—C8—C7 | 114.63 (16) | C2—O1—C1 | 117.61 (16) |
C10—C11—C12 | 136.69 (17) | C8—O3—C11 | 107.83 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg1i | 0.93 | 2.80 | 3.541 (1) | 137 |
C16—H16···Cg2ii | 0.93 | 2.95 | 3.722 (1) | 142 |
C18—H18A···Cg3iii | 0.96 | 3.24 | 4.091 (1) | 149 |
Symmetry codes: (i) x, −y+1, z−3/2; (ii) x, −y, z−1/2; (iii) x, y−1, z. |
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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 π–π 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].