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In the title compound, C24H20O9, the dihedral angle between the two benzene rings is 2.32 (13)°. The mol­ecular conformation is stabilized by some weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012044/bt2295sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012044/bt2295Isup2.hkl
Contains datablock I

CCDC reference: 642930

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.161
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.06 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.41 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C8 .. 5.31 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C23 - C24 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Diethyl 2,5-bis(1,3-benzodioxol-5-yl)furan-3,4-dicarboxylate top
Crystal data top
C24H20O9Z = 2
Mr = 452.40F(000) = 472
Triclinic, P1Dx = 1.421 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7835 (17) ÅCell parameters from 1687 reflections
b = 10.6602 (18) Åθ = 2.3–25.9°
c = 11.3040 (19) ŵ = 0.11 mm1
α = 85.684 (3)°T = 292 K
β = 84.100 (3)°Block, colorless
γ = 64.454 (3)°0.30 × 0.20 × 0.10 mm
V = 1057.4 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
φ and ω scansh = 911
5360 measured reflectionsk = 1212
3674 independent reflectionsl = 1311
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.2639P]
where P = (Fo2 + 2Fc2)/3
3674 reflections(Δ/σ)max < 0.001
300 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 e Å3
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
C11.5373 (3)0.2324 (3)0.6319 (3)0.0723 (8)
H1A1.63610.23080.61990.087*
H1B1.52360.26230.71370.087*
C21.4050 (3)0.2483 (3)0.4899 (2)0.0559 (7)
C31.3487 (3)0.2902 (3)0.4042 (3)0.0717 (9)
H31.39090.38250.38220.086*
C41.2244 (3)0.1883 (3)0.3505 (3)0.0633 (8)
H41.18310.21430.29150.076*
C51.1598 (3)0.0506 (2)0.3810 (2)0.0459 (6)
C61.2193 (3)0.0105 (3)0.4717 (2)0.0500 (6)
H61.17750.08090.49600.060*
C71.3420 (3)0.1126 (3)0.5226 (2)0.0519 (6)
C81.0338 (3)0.0507 (2)0.3154 (2)0.0430 (6)
C90.9554 (3)0.1929 (2)0.3014 (2)0.0440 (6)
C100.8499 (3)0.2183 (2)0.2132 (2)0.0440 (6)
C110.8699 (2)0.0925 (2)0.1772 (2)0.0430 (6)
C120.8094 (2)0.0436 (2)0.0885 (2)0.0415 (5)
C130.8812 (3)0.0947 (2)0.0560 (2)0.0463 (6)
H130.96680.15480.09380.056*
C140.8306 (3)0.1465 (2)0.0300 (2)0.0479 (6)
H140.87960.23950.05000.057*
C150.7052 (3)0.0546 (2)0.0842 (2)0.0448 (6)
C160.6333 (3)0.0822 (2)0.0553 (2)0.0444 (6)
C170.6797 (3)0.1357 (2)0.0305 (2)0.0479 (6)
H170.62820.22880.05000.057*
C180.5131 (3)0.0519 (3)0.2008 (2)0.0542 (7)
H18A0.41650.04590.19410.065*
H18B0.53240.08000.28210.065*
C190.9734 (3)0.3031 (3)0.3591 (2)0.0543 (7)
C200.8828 (4)0.5466 (3)0.3699 (3)0.0786 (10)
H20A0.98530.53960.36740.094*
H20B0.84280.55110.45240.094*
C210.7863 (4)0.6721 (3)0.3025 (3)0.0960 (12)
H21A0.82660.66650.22100.144*
H21B0.78450.75290.33620.144*
H21C0.68490.67870.30640.144*
C220.7444 (3)0.3548 (3)0.1607 (2)0.0511 (6)
C230.7199 (4)0.5202 (3)0.0023 (3)0.0942 (12)
H23A0.61910.52580.00310.113*
H23B0.70990.59960.04500.113*
C240.7901 (6)0.5223 (4)0.1135 (4)0.1272 (17)
H24A0.89500.50170.10820.191*
H24B0.73950.61280.15070.191*
H24C0.78330.45380.16020.191*
O11.5289 (2)0.3252 (2)0.55368 (18)0.0742 (6)
O21.4214 (2)0.0974 (2)0.60913 (17)0.0750 (6)
O30.98038 (17)0.00952 (16)0.24080 (14)0.0463 (4)
O40.63233 (19)0.08012 (18)0.17055 (16)0.0581 (5)
O50.50915 (19)0.15117 (18)0.12015 (16)0.0609 (5)
O61.0558 (3)0.2901 (2)0.4347 (2)0.1048 (9)
O70.8842 (2)0.42694 (18)0.31612 (18)0.0706 (6)
O80.6144 (2)0.4194 (2)0.1944 (2)0.0845 (7)
O90.8122 (2)0.39163 (19)0.06604 (18)0.0678 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0706 (19)0.075 (2)0.0694 (19)0.0247 (17)0.0327 (16)0.0062 (16)
C20.0552 (15)0.0494 (15)0.0584 (16)0.0163 (13)0.0196 (13)0.0081 (13)
C30.081 (2)0.0432 (15)0.086 (2)0.0141 (15)0.0362 (17)0.0051 (14)
C40.0693 (18)0.0472 (15)0.0741 (19)0.0195 (14)0.0338 (15)0.0023 (13)
C50.0452 (13)0.0452 (14)0.0484 (14)0.0201 (11)0.0095 (11)0.0033 (11)
C60.0544 (15)0.0454 (14)0.0476 (14)0.0174 (12)0.0108 (12)0.0018 (11)
C70.0570 (15)0.0564 (16)0.0442 (14)0.0242 (13)0.0144 (12)0.0014 (12)
C80.0470 (13)0.0466 (14)0.0400 (13)0.0226 (11)0.0086 (10)0.0059 (10)
C90.0421 (13)0.0434 (13)0.0472 (14)0.0172 (11)0.0083 (11)0.0052 (11)
C100.0382 (12)0.0417 (13)0.0505 (14)0.0147 (10)0.0059 (10)0.0042 (11)
C110.0383 (12)0.0401 (13)0.0488 (14)0.0142 (10)0.0093 (10)0.0010 (11)
C120.0409 (12)0.0425 (13)0.0439 (13)0.0195 (11)0.0071 (10)0.0025 (10)
C130.0406 (13)0.0405 (13)0.0566 (15)0.0148 (11)0.0127 (11)0.0018 (11)
C140.0469 (14)0.0375 (13)0.0579 (15)0.0148 (11)0.0091 (12)0.0070 (11)
C150.0443 (13)0.0475 (14)0.0465 (14)0.0222 (11)0.0075 (11)0.0029 (11)
C160.0385 (12)0.0448 (14)0.0489 (14)0.0156 (11)0.0111 (10)0.0013 (11)
C170.0434 (13)0.0382 (13)0.0597 (16)0.0134 (11)0.0113 (12)0.0032 (11)
C180.0523 (15)0.0581 (16)0.0528 (15)0.0216 (13)0.0178 (12)0.0015 (12)
C190.0520 (15)0.0460 (15)0.0626 (16)0.0155 (12)0.0184 (13)0.0028 (12)
C200.104 (2)0.0448 (16)0.086 (2)0.0220 (16)0.0425 (19)0.0083 (15)
C210.124 (3)0.0508 (18)0.106 (3)0.0228 (19)0.049 (2)0.0019 (18)
C220.0466 (15)0.0423 (14)0.0644 (17)0.0153 (12)0.0150 (13)0.0098 (12)
C230.093 (3)0.0559 (19)0.102 (3)0.0016 (17)0.028 (2)0.0253 (19)
C240.184 (5)0.087 (3)0.082 (3)0.029 (3)0.039 (3)0.028 (2)
O10.0739 (13)0.0614 (12)0.0755 (13)0.0121 (10)0.0387 (11)0.0064 (10)
O20.0831 (14)0.0678 (13)0.0690 (13)0.0198 (11)0.0425 (11)0.0015 (10)
O30.0466 (9)0.0402 (9)0.0526 (10)0.0169 (8)0.0152 (8)0.0004 (7)
O40.0570 (11)0.0548 (11)0.0634 (11)0.0201 (9)0.0209 (9)0.0087 (9)
O50.0537 (11)0.0528 (11)0.0695 (12)0.0108 (9)0.0279 (9)0.0057 (9)
O60.1208 (19)0.0486 (12)0.144 (2)0.0172 (13)0.0908 (18)0.0086 (13)
O70.0898 (14)0.0419 (10)0.0794 (13)0.0197 (10)0.0428 (11)0.0023 (9)
O80.0464 (12)0.0596 (13)0.128 (2)0.0058 (10)0.0014 (12)0.0008 (12)
O90.0605 (12)0.0492 (11)0.0710 (13)0.0038 (9)0.0088 (10)0.0137 (9)
Geometric parameters (Å, º) top
C1—O11.409 (4)C14—H140.9300
C1—O21.421 (3)C15—C161.366 (3)
C1—H1A0.9700C15—O41.374 (3)
C1—H1B0.9700C16—C171.368 (3)
C2—C31.353 (4)C16—O51.373 (3)
C2—C71.368 (4)C17—H170.9300
C2—O11.376 (3)C18—O41.433 (3)
C3—C41.393 (3)C18—O51.433 (3)
C3—H30.9300C18—H18A0.9700
C4—C51.380 (4)C18—H18B0.9700
C4—H40.9300C19—O61.195 (3)
C5—C61.406 (3)C19—O71.318 (3)
C5—C81.468 (3)C20—O71.448 (3)
C6—C71.370 (3)C20—C211.472 (4)
C6—H60.9300C20—H20A0.9700
C7—O21.370 (3)C20—H20B0.9700
C8—O31.363 (3)C21—H21A0.9600
C8—C91.378 (3)C21—H21B0.9600
C9—C101.436 (3)C21—H21C0.9600
C9—C191.468 (3)C22—O81.192 (3)
C10—C111.357 (3)C22—O91.325 (3)
C10—C221.495 (3)C23—C241.418 (5)
C11—O31.377 (3)C23—O91.459 (3)
C11—C121.448 (3)C23—H23A0.9700
C12—C131.392 (3)C23—H23B0.9700
C12—C171.415 (3)C24—H24A0.9600
C13—C141.381 (3)C24—H24B0.9600
C13—H130.9300C24—H24C0.9600
C14—C151.367 (3)
O1—C1—O2108.7 (2)C15—C16—O5110.3 (2)
O1—C1—H1A109.9C17—C16—O5127.0 (2)
O2—C1—H1A109.9C16—C17—C12117.2 (2)
O1—C1—H1B109.9C16—C17—H17121.4
O2—C1—H1B109.9C12—C17—H17121.4
H1A—C1—H1B108.3O4—C18—O5107.83 (18)
C3—C2—C7121.5 (2)O4—C18—H18A110.1
C3—C2—O1128.7 (3)O5—C18—H18A110.1
C7—C2—O1109.8 (2)O4—C18—H18B110.1
C2—C3—C4116.7 (3)O5—C18—H18B110.1
C2—C3—H3121.7H18A—C18—H18B108.5
C4—C3—H3121.7O6—C19—O7121.3 (2)
C5—C4—C3123.0 (2)O6—C19—C9127.7 (2)
C5—C4—H4118.5O7—C19—C9111.0 (2)
C3—C4—H4118.5O7—C20—C21108.0 (2)
C4—C5—C6119.1 (2)O7—C20—H20A110.1
C4—C5—C8119.1 (2)C21—C20—H20A110.1
C6—C5—C8121.8 (2)O7—C20—H20B110.1
C7—C6—C5116.7 (2)C21—C20—H20B110.1
C7—C6—H6121.6H20A—C20—H20B108.4
C5—C6—H6121.6C20—C21—H21A109.5
C2—C7—O2109.9 (2)C20—C21—H21B109.5
C2—C7—C6123.1 (2)H21A—C21—H21B109.5
O2—C7—C6127.1 (2)C20—C21—H21C109.5
O3—C8—C9108.04 (19)H21A—C21—H21C109.5
O3—C8—C5113.21 (19)H21B—C21—H21C109.5
C9—C8—C5138.7 (2)O8—C22—O9123.7 (2)
C8—C9—C10106.9 (2)O8—C22—C10125.4 (3)
C8—C9—C19129.1 (2)O9—C22—C10110.7 (2)
C10—C9—C19124.0 (2)C24—C23—O9109.4 (3)
C11—C10—C9107.2 (2)C24—C23—H23A109.8
C11—C10—C22124.4 (2)O9—C23—H23A109.8
C9—C10—C22128.3 (2)C24—C23—H23B109.8
C10—C11—O3108.42 (19)O9—C23—H23B109.8
C10—C11—C12136.0 (2)H23A—C23—H23B108.2
O3—C11—C12115.57 (19)C23—C24—H24A109.5
C13—C12—C17118.8 (2)C23—C24—H24B109.5
C13—C12—C11120.3 (2)H24A—C24—H24B109.5
C17—C12—C11120.9 (2)C23—C24—H24C109.5
C14—C13—C12122.8 (2)H24A—C24—H24C109.5
C14—C13—H13118.6H24B—C24—H24C109.5
C12—C13—H13118.6C2—O1—C1105.8 (2)
C15—C14—C13116.8 (2)C7—O2—C1105.7 (2)
C15—C14—H14121.6C8—O3—C11109.46 (17)
C13—C14—H14121.6C15—O4—C18105.68 (18)
C16—C15—C14121.8 (2)C16—O5—C18105.57 (18)
C16—C15—O4110.2 (2)C19—O7—C20117.2 (2)
C14—C15—O4128.0 (2)C22—O9—C23116.7 (2)
C15—C16—C17122.6 (2)
C7—C2—C3—C40.5 (5)C14—C15—C16—C171.2 (4)
O1—C2—C3—C4177.5 (3)O4—C15—C16—C17178.3 (2)
C2—C3—C4—C50.2 (5)C14—C15—C16—O5178.5 (2)
C3—C4—C5—C61.2 (4)O4—C15—C16—O51.0 (3)
C3—C4—C5—C8177.0 (3)C15—C16—C17—C121.2 (4)
C4—C5—C6—C71.4 (4)O5—C16—C17—C12178.1 (2)
C8—C5—C6—C7176.7 (2)C13—C12—C17—C160.4 (3)
C3—C2—C7—O2178.9 (3)C11—C12—C17—C16177.6 (2)
O1—C2—C7—O20.6 (3)C8—C9—C19—O64.1 (5)
C3—C2—C7—C60.2 (4)C10—C9—C19—O6178.1 (3)
O1—C2—C7—C6178.1 (2)C8—C9—C19—O7175.6 (2)
C5—C6—C7—C20.7 (4)C10—C9—C19—O72.2 (4)
C5—C6—C7—O2177.7 (2)C11—C10—C22—O890.2 (4)
C4—C5—C8—O39.0 (3)C9—C10—C22—O895.1 (3)
C6—C5—C8—O3172.9 (2)C11—C10—C22—O986.1 (3)
C4—C5—C8—C9166.7 (3)C9—C10—C22—O988.7 (3)
C6—C5—C8—C911.4 (4)C3—C2—O1—C1179.5 (3)
O3—C8—C9—C100.2 (3)C7—C2—O1—C12.3 (3)
C5—C8—C9—C10175.7 (3)O2—C1—O1—C23.2 (3)
O3—C8—C9—C19178.2 (2)C2—C7—O2—C11.4 (3)
C5—C8—C9—C192.4 (5)C6—C7—O2—C1180.0 (3)
C8—C9—C10—C110.7 (3)O1—C1—O2—C72.8 (3)
C19—C9—C10—C11177.5 (2)C9—C8—O3—C111.0 (2)
C8—C9—C10—C22176.2 (2)C5—C8—O3—C11176.03 (19)
C19—C9—C10—C222.0 (4)C10—C11—O3—C81.5 (3)
C9—C10—C11—O31.3 (3)C12—C11—O3—C8176.22 (19)
C22—C10—C11—O3177.0 (2)C16—C15—O4—C183.4 (3)
C9—C10—C11—C12175.7 (3)C14—C15—O4—C18177.1 (2)
C22—C10—C11—C120.0 (4)O5—C18—O4—C156.3 (3)
C10—C11—C12—C13164.8 (3)C15—C16—O5—C184.9 (3)
O3—C11—C12—C1312.0 (3)C17—C16—O5—C18177.9 (2)
C10—C11—C12—C1713.2 (4)O4—C18—O5—C166.9 (3)
O3—C11—C12—C17170.0 (2)O6—C19—O7—C204.0 (4)
C17—C12—C13—C140.5 (4)C9—C19—O7—C20176.3 (2)
C11—C12—C13—C14178.5 (2)C21—C20—O7—C19175.4 (3)
C12—C13—C14—C150.6 (4)O8—C22—O9—C230.9 (4)
C13—C14—C15—C160.2 (4)C10—C22—O9—C23177.2 (2)
C13—C14—C15—O4179.2 (2)C24—C23—O9—C22161.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O60.932.132.918 (3)142
C4—H4···O30.932.312.683 (4)103
C13—H13···O30.932.412.755 (3)102
 

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