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The structure of the title compound, C11H8O3, contains two crystallographically independent mol­ecules in the asymmetric unit, both of them located in general positions. Both mol­ecules are non-planar; the dihedral angles between the fur­yl rings are 10.43 (6) and 11.59 (7)°. The crystal structure is stabilized by weak intra- and inter­molecular C—H...O and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011244/nc6027sup1.cif
Contains datablocks zu09, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011244/nc6027Isup2.hkl
Contains datablock I

CCDC reference: 257537

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.095
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,3-di(2-furyl)-2-propen-1-one top
Crystal data top
C11H8O3F(000) = 784
Mr = 188.17Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 34010 reflections
a = 15.142 (1) Åθ = 1.4–27.3°
b = 11.6395 (8) ŵ = 0.10 mm1
c = 11.2429 (14) ÅT = 293 K
β = 111.363 (7)°Prism., yellow
V = 1845.4 (3) Å30.56 × 0.46 × 0.32 mm
Z = 8
Data collection top
Stoe IPDS 2
diffractometer
3179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 26.8°, θmin = 1.4°
Detector resolution: 6.67 pixels mm-1h = 1919
ω scansk = 1414
35020 measured reflectionsl = 1414
3920 independent reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0433P)2 + 0.2469P]
where P = (Fo2 + 2Fc2)/3
3920 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.13 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
C1A0.36966 (13)0.07673 (14)0.74547 (19)0.0792 (5)
C1B0.13225 (12)0.08128 (13)0.35656 (17)0.0717 (4)
C2A0.33543 (13)0.08986 (15)0.83800 (19)0.0799 (5)
C2B0.16060 (12)0.08778 (14)0.48230 (17)0.0730 (4)
C3A0.33940 (11)0.20832 (14)0.86525 (15)0.0647 (4)
C3B0.15518 (10)0.20476 (13)0.51240 (14)0.0594 (3)
C4A0.37535 (9)0.25979 (12)0.78540 (12)0.0537 (3)
C4B0.12305 (9)0.26177 (10)0.40063 (11)0.0490 (3)
C5A0.39986 (10)0.37840 (12)0.77023 (13)0.0575 (3)
C5B0.09966 (9)0.38171 (11)0.36567 (11)0.0526 (3)
C6A0.37972 (10)0.46342 (12)0.85295 (13)0.0557 (3)
C6B0.12119 (10)0.46455 (11)0.47075 (12)0.0531 (3)
C7A0.40803 (10)0.57163 (12)0.85584 (12)0.0532 (3)
C7B0.09331 (9)0.57299 (11)0.44752 (12)0.0507 (3)
C8A0.39432 (9)0.66297 (11)0.93222 (11)0.0499 (3)
C8B0.10720 (8)0.66427 (10)0.53744 (11)0.0470 (3)
C9A0.42106 (11)0.77396 (12)0.94488 (13)0.0584 (3)
C9B0.08015 (10)0.77573 (11)0.52310 (13)0.0539 (3)
C10A0.38760 (12)0.82360 (13)1.03516 (13)0.0643 (4)
C10B0.11290 (11)0.82568 (12)0.64577 (13)0.0585 (3)
C11A0.34253 (11)0.74070 (13)1.07115 (14)0.0633 (4)
C11B0.15780 (11)0.74285 (12)0.72660 (13)0.0591 (3)
O1A0.39443 (8)0.17939 (9)0.70979 (10)0.0707 (3)
O1B0.10839 (7)0.18651 (8)0.30226 (9)0.0638 (3)
O2A0.43581 (10)0.40477 (10)0.69239 (11)0.0860 (4)
O2B0.06387 (9)0.41066 (9)0.25381 (9)0.0766 (3)
O3A0.34450 (7)0.63979 (8)1.01030 (8)0.0584 (2)
O3B0.15621 (7)0.64185 (8)0.66433 (8)0.0561 (2)
H1A0.3797 (14)0.0114 (18)0.6955 (19)0.103 (6)*
H1B0.1231 (13)0.0207 (17)0.2954 (18)0.098 (6)*
H2A0.3132 (14)0.0335 (17)0.8771 (18)0.098 (6)*
H2B0.1780 (13)0.0274 (17)0.5377 (18)0.098 (6)*
H3A0.3246 (11)0.2427 (13)0.9275 (15)0.070 (5)*
H3B0.1676 (11)0.2352 (13)0.5901 (16)0.070 (4)*
H6A0.3495 (11)0.4370 (13)0.9080 (15)0.071 (4)*
H6B0.1571 (11)0.4365 (13)0.5565 (15)0.070 (4)*
H7A0.4424 (10)0.5942 (13)0.8034 (14)0.066 (4)*
H7B0.0590 (10)0.5958 (12)0.3616 (14)0.063 (4)*
H9A0.4574 (11)0.8124 (13)0.9012 (14)0.072 (4)*
H9B0.0440 (10)0.8121 (13)0.4441 (14)0.067 (4)*
H10A0.3938 (11)0.8985 (15)1.0619 (15)0.074 (5)*
H10B0.1044 (11)0.9041 (14)0.6677 (14)0.071 (4)*
H11A0.3110 (12)0.7378 (14)1.1290 (16)0.076 (5)*
H11B0.1902 (11)0.7395 (13)0.8168 (16)0.073 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0796 (11)0.0550 (9)0.1009 (12)0.0031 (8)0.0303 (10)0.0103 (9)
C1B0.0774 (10)0.0474 (8)0.0836 (11)0.0000 (7)0.0213 (8)0.0097 (7)
C2A0.0814 (11)0.0620 (10)0.0957 (12)0.0012 (8)0.0315 (10)0.0136 (9)
C2B0.0792 (10)0.0520 (8)0.0823 (11)0.0020 (7)0.0229 (8)0.0108 (7)
C3A0.0684 (9)0.0642 (9)0.0658 (8)0.0038 (7)0.0296 (7)0.0035 (7)
C3B0.0655 (8)0.0583 (8)0.0529 (7)0.0016 (6)0.0198 (6)0.0012 (6)
C4A0.0510 (7)0.0567 (7)0.0545 (7)0.0052 (5)0.0206 (5)0.0041 (6)
C4B0.0503 (7)0.0485 (6)0.0479 (6)0.0037 (5)0.0177 (5)0.0059 (5)
C5A0.0621 (8)0.0589 (8)0.0583 (7)0.0040 (6)0.0300 (6)0.0012 (6)
C5B0.0589 (7)0.0498 (7)0.0467 (6)0.0028 (6)0.0162 (5)0.0021 (5)
C6A0.0596 (8)0.0576 (8)0.0566 (7)0.0014 (6)0.0292 (6)0.0011 (6)
C6B0.0618 (8)0.0496 (7)0.0464 (6)0.0004 (6)0.0180 (6)0.0015 (5)
C7A0.0566 (7)0.0571 (8)0.0500 (6)0.0053 (6)0.0241 (6)0.0033 (5)
C7B0.0553 (7)0.0517 (7)0.0456 (6)0.0031 (5)0.0191 (5)0.0004 (5)
C8A0.0530 (7)0.0533 (7)0.0460 (6)0.0032 (5)0.0212 (5)0.0049 (5)
C8B0.0521 (6)0.0468 (6)0.0429 (6)0.0003 (5)0.0182 (5)0.0027 (5)
C9A0.0670 (8)0.0551 (7)0.0528 (7)0.0043 (6)0.0216 (6)0.0035 (6)
C9B0.0622 (8)0.0509 (7)0.0513 (7)0.0054 (6)0.0240 (6)0.0053 (5)
C10A0.0831 (10)0.0518 (8)0.0535 (7)0.0035 (7)0.0197 (7)0.0035 (6)
C10B0.0758 (9)0.0470 (7)0.0614 (8)0.0017 (6)0.0354 (7)0.0044 (6)
C11A0.0778 (9)0.0630 (9)0.0545 (7)0.0077 (7)0.0305 (7)0.0049 (6)
C11B0.0734 (9)0.0584 (8)0.0468 (7)0.0006 (6)0.0234 (6)0.0073 (6)
O1A0.0811 (7)0.0600 (6)0.0785 (7)0.0029 (5)0.0379 (6)0.0134 (5)
O1B0.0800 (6)0.0518 (5)0.0562 (5)0.0017 (5)0.0207 (5)0.0112 (4)
O2A0.1283 (10)0.0679 (7)0.0945 (8)0.0034 (7)0.0796 (8)0.0053 (6)
O2B0.1134 (9)0.0567 (6)0.0461 (5)0.0022 (6)0.0131 (5)0.0001 (4)
O3A0.0719 (6)0.0543 (5)0.0595 (5)0.0005 (4)0.0364 (5)0.0004 (4)
O3B0.0719 (6)0.0501 (5)0.0441 (4)0.0055 (4)0.0187 (4)0.0025 (4)
Geometric parameters (Å, º) top
C1A—C2A1.329 (3)C6A—H6A0.946 (16)
C1A—O1A1.356 (2)C6B—C7B1.3264 (18)
C1A—H1A0.99 (2)C6B—H6B0.974 (15)
C1B—C2B1.321 (2)C7A—C8A1.4285 (18)
C1B—O1B1.3575 (18)C7A—H7A0.954 (15)
C1B—H1B0.96 (2)C7B—C8B1.4283 (17)
C2A—C3A1.409 (2)C7B—H7B0.953 (15)
C2A—H2A0.92 (2)C8A—C9A1.3458 (19)
C2B—C3B1.413 (2)C8A—O3A1.3766 (15)
C2B—H2B0.912 (19)C8B—C9B1.3523 (18)
C3A—C4A1.348 (2)C8B—O3B1.3721 (14)
C3A—H3A0.902 (16)C9A—C10A1.413 (2)
C3B—C4B1.3456 (18)C9A—H9A0.970 (16)
C3B—H3B0.896 (16)C9B—C10B1.4099 (19)
C4A—O1A1.3641 (16)C9B—H9B0.956 (15)
C4A—C5A1.456 (2)C10A—C11A1.327 (2)
C4B—O1B1.3642 (15)C10A—H10A0.916 (17)
C4B—C5B1.4586 (18)C10B—C11B1.329 (2)
C5A—O2A1.2261 (16)C10B—H10B0.967 (16)
C5A—C6A1.4641 (18)C11A—O3A1.3651 (16)
C5B—O2B1.2216 (15)C11A—H11A0.937 (17)
C5B—C6B1.4667 (17)C11B—O3B1.3640 (16)
C6A—C7A1.3270 (19)C11B—H11B0.953 (16)
C2A—C1A—O1A111.03 (15)C5B—C6B—H6B117.2 (9)
C2A—C1A—H1A135.8 (12)C6A—C7A—C8A127.21 (12)
O1A—C1A—H1A113.1 (12)C6A—C7A—H7A119.3 (9)
C2B—C1B—O1B111.03 (14)C8A—C7A—H7A113.5 (9)
C2B—C1B—H1B135.6 (12)C6B—C7B—C8B127.90 (12)
O1B—C1B—H1B113.3 (12)C6B—C7B—H7B118.8 (9)
C1A—C2A—C3A106.55 (16)C8B—C7B—H7B113.3 (9)
C1A—C2A—H2A127.4 (12)C9A—C8A—O3A109.53 (11)
C3A—C2A—H2A126.1 (12)C9A—C8A—C7A132.38 (12)
C1B—C2B—C3B106.68 (14)O3A—C8A—C7A118.09 (11)
C1B—C2B—H2B125.9 (12)C9B—C8B—O3B109.39 (11)
C3B—C2B—H2B127.4 (12)C9B—C8B—C7B132.00 (12)
C4A—C3A—C2A106.60 (15)O3B—C8B—C7B118.61 (11)
C4A—C3A—H3A126.4 (10)C8A—C9A—C10A107.21 (13)
C2A—C3A—H3A126.8 (10)C8A—C9A—H9A126.4 (9)
C4B—C3B—C2B106.52 (13)C10A—C9A—H9A126.4 (9)
C4B—C3B—H3B126.2 (10)C8B—C9B—C10B107.20 (12)
C2B—C3B—H3B127.2 (10)C8B—C9B—H9B125.6 (9)
C3A—C4A—O1A109.80 (13)C10B—C9B—H9B127.2 (9)
C3A—C4A—C5A132.96 (13)C11A—C10A—C9A106.29 (13)
O1A—C4A—C5A117.17 (12)C11A—C10A—H10A126.5 (10)
C3B—C4B—O1B109.71 (12)C9A—C10A—H10A127.2 (10)
C3B—C4B—C5B133.90 (12)C11B—C10B—C9B106.24 (12)
O1B—C4B—C5B116.38 (11)C11B—C10B—H10B126.4 (9)
O2A—C5A—C4A121.30 (12)C9B—C10B—H10B127.4 (9)
O2A—C5A—C6A122.24 (13)C10A—C11A—O3A111.42 (13)
C4A—C5A—C6A116.46 (12)C10A—C11A—H11A133.3 (10)
O2B—C5B—C4B120.97 (11)O3A—C11A—H11A115.3 (10)
O2B—C5B—C6B122.21 (12)C10B—C11B—O3B111.42 (12)
C4B—C5B—C6B116.82 (11)C10B—C11B—H11B133.9 (10)
C7A—C6A—C5A121.12 (13)O3B—C11B—H11B114.7 (10)
C7A—C6A—H6A121.5 (9)C1A—O1A—C4A106.01 (13)
C5A—C6A—H6A117.3 (9)C1B—O1B—C4B106.06 (11)
C7B—C6B—C5B120.37 (12)C11A—O3A—C8A105.55 (11)
C7B—C6B—H6B122.5 (9)C11B—O3B—C8B105.75 (10)
O1A—C1A—C2A—C3A0.8 (2)C6A—C7A—C8A—O3A1.7 (2)
O1B—C1B—C2B—C3B0.1 (2)C6B—C7B—C8B—C9B178.62 (15)
C1A—C2A—C3A—C4A0.6 (2)C6B—C7B—C8B—O3B1.1 (2)
C1B—C2B—C3B—C4B0.19 (19)O3A—C8A—C9A—C10A0.39 (15)
C2A—C3A—C4A—O1A0.22 (17)C7A—C8A—C9A—C10A179.84 (14)
C2A—C3A—C4A—C5A177.22 (15)O3B—C8B—C9B—C10B0.30 (15)
C2B—C3B—C4B—O1B0.18 (16)C7B—C8B—C9B—C10B179.44 (13)
C2B—C3B—C4B—C5B177.97 (15)C8A—C9A—C10A—C11A0.31 (17)
C3A—C4A—C5A—O2A177.09 (16)C8B—C9B—C10B—C11B0.27 (16)
O1A—C4A—C5A—O2A0.3 (2)C9A—C10A—C11A—O3A0.11 (18)
C3A—C4A—C5A—C6A2.6 (2)C9B—C10B—C11B—O3B0.14 (17)
O1A—C4A—C5A—C6A179.45 (12)C2A—C1A—O1A—C4A0.67 (19)
C3B—C4B—C5B—O2B174.04 (15)C3A—C4A—O1A—C1A0.25 (16)
O1B—C4B—C5B—O2B4.02 (19)C5A—C4A—O1A—C1A177.27 (13)
C3B—C4B—C5B—C6B6.0 (2)C2B—C1B—O1B—C4B0.02 (18)
O1B—C4B—C5B—C6B175.96 (11)C3B—C4B—O1B—C1B0.10 (16)
O2A—C5A—C6A—C7A6.6 (2)C5B—C4B—O1B—C1B178.41 (12)
C4A—C5A—C6A—C7A173.12 (13)C10A—C11A—O3A—C8A0.12 (16)
O2B—C5B—C6B—C7B6.9 (2)C9A—C8A—O3A—C11A0.32 (14)
C4B—C5B—C6B—C7B173.10 (12)C7A—C8A—O3A—C11A179.87 (11)
C5A—C6A—C7A—C8A179.34 (12)C10B—C11B—O3B—C8B0.04 (16)
C5B—C6B—C7B—C8B179.39 (12)C9B—C8B—O3B—C11B0.22 (14)
C6A—C7A—C8A—C9A178.52 (15)C7B—C8B—O3B—C11B179.56 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1B—H1B···O3Bi0.96 (2)2.56 (2)3.4812 (19)161.7 (16)
C9A—H9A···O2Aii0.970 (16)2.474 (16)3.4402 (18)174.4 (13)
C9B—H9B···O2Biii0.956 (15)2.507 (16)3.4596 (17)174.2 (12)
C10B—H10B···O2Biv0.967 (16)2.528 (17)3.4786 (17)167.6 (12)
C11A—H11A···Cg4v0.937 (17)2.837 (19)3.5765 (19)136.67 (13)
C11B—H11B···Cg3vi0.953 (16)2.838 (17)3.6160 (17)139.53 (14)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x, y+3/2, z+1/2; (v) x, y1, z; (vi) x, y1/2, z1/2.
 

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