(E)-1,3-Di(2-fur­yl)-2-propen-1-one

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

C11H8O3	F(000) = 784
Mr = 188.17	Dx = 1.355 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 34010 reflections
a = 15.142 (1) Å	θ = 1.4–27.3°
b = 11.6395 (8) Å	µ = 0.10 mm^−1
c = 11.2429 (14) Å	T = 293 K
β = 111.363 (7)°	Prism., yellow
V = 1845.4 (3) Å^3	0.56 × 0.46 × 0.32 mm
Z = 8

Data collection

Stoe IPDS 2 diffractometer	3179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 26.8°, θmin = 1.4°
Detector resolution: 6.67 pixels mm^-1	h = −19→19
ω scans	k = −14→14
35020 measured reflections	l = −14→14
3920 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.2469P] where P = (Fo^2 + 2Fc^2)/3
3920 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.36966 (13)	0.07673 (14)	0.74547 (19)	0.0792 (5)
C1B	0.13225 (12)	0.08128 (13)	0.35656 (17)	0.0717 (4)
C2A	0.33543 (13)	0.08986 (15)	0.83800 (19)	0.0799 (5)
C2B	0.16060 (12)	0.08778 (14)	0.48230 (17)	0.0730 (4)
C3A	0.33940 (11)	0.20832 (14)	0.86525 (15)	0.0647 (4)
C3B	0.15518 (10)	0.20476 (13)	0.51240 (14)	0.0594 (3)
C4A	0.37535 (9)	0.25979 (12)	0.78540 (12)	0.0537 (3)
C4B	0.12305 (9)	0.26177 (10)	0.40063 (11)	0.0490 (3)
C5A	0.39986 (10)	0.37840 (12)	0.77023 (13)	0.0575 (3)
C5B	0.09966 (9)	0.38171 (11)	0.36567 (11)	0.0526 (3)
C6A	0.37972 (10)	0.46342 (12)	0.85295 (13)	0.0557 (3)
C6B	0.12119 (10)	0.46455 (11)	0.47075 (12)	0.0531 (3)
C7A	0.40803 (10)	0.57163 (12)	0.85584 (12)	0.0532 (3)
C7B	0.09331 (9)	0.57299 (11)	0.44752 (12)	0.0507 (3)
C8A	0.39432 (9)	0.66297 (11)	0.93222 (11)	0.0499 (3)
C8B	0.10720 (8)	0.66427 (10)	0.53744 (11)	0.0470 (3)
C9A	0.42106 (11)	0.77396 (12)	0.94488 (13)	0.0584 (3)
C9B	0.08015 (10)	0.77573 (11)	0.52310 (13)	0.0539 (3)
C10A	0.38760 (12)	0.82360 (13)	1.03516 (13)	0.0643 (4)
C10B	0.11290 (11)	0.82568 (12)	0.64577 (13)	0.0585 (3)
C11A	0.34253 (11)	0.74070 (13)	1.07115 (14)	0.0633 (4)
C11B	0.15780 (11)	0.74285 (12)	0.72660 (13)	0.0591 (3)
O1A	0.39443 (8)	0.17939 (9)	0.70979 (10)	0.0707 (3)
O1B	0.10839 (7)	0.18651 (8)	0.30226 (9)	0.0638 (3)
O2A	0.43581 (10)	0.40477 (10)	0.69239 (11)	0.0860 (4)
O2B	0.06387 (9)	0.41066 (9)	0.25381 (9)	0.0766 (3)
O3A	0.34450 (7)	0.63979 (8)	1.01030 (8)	0.0584 (2)
O3B	0.15621 (7)	0.64185 (8)	0.66433 (8)	0.0561 (2)
H1A	0.3797 (14)	0.0114 (18)	0.6955 (19)	0.103 (6)*
H1B	0.1231 (13)	0.0207 (17)	0.2954 (18)	0.098 (6)*
H2A	0.3132 (14)	0.0335 (17)	0.8771 (18)	0.098 (6)*
H2B	0.1780 (13)	0.0274 (17)	0.5377 (18)	0.098 (6)*
H3A	0.3246 (11)	0.2427 (13)	0.9275 (15)	0.070 (5)*
H3B	0.1676 (11)	0.2352 (13)	0.5901 (16)	0.070 (4)*
H6A	0.3495 (11)	0.4370 (13)	0.9080 (15)	0.071 (4)*
H6B	0.1571 (11)	0.4365 (13)	0.5565 (15)	0.070 (4)*
H7A	0.4424 (10)	0.5942 (13)	0.8034 (14)	0.066 (4)*
H7B	0.0590 (10)	0.5958 (12)	0.3616 (14)	0.063 (4)*
H9A	0.4574 (11)	0.8124 (13)	0.9012 (14)	0.072 (4)*
H9B	0.0440 (10)	0.8121 (13)	0.4441 (14)	0.067 (4)*
H10A	0.3938 (11)	0.8985 (15)	1.0619 (15)	0.074 (5)*
H10B	0.1044 (11)	0.9041 (14)	0.6677 (14)	0.071 (4)*
H11A	0.3110 (12)	0.7378 (14)	1.1290 (16)	0.076 (5)*
H11B	0.1902 (11)	0.7395 (13)	0.8168 (16)	0.073 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0796 (11)	0.0550 (9)	0.1009 (12)	0.0031 (8)	0.0303 (10)	−0.0103 (9)
C1B	0.0774 (10)	0.0474 (8)	0.0836 (11)	0.0000 (7)	0.0213 (8)	−0.0097 (7)
C2A	0.0814 (11)	0.0620 (10)	0.0957 (12)	−0.0012 (8)	0.0315 (10)	0.0136 (9)
C2B	0.0792 (10)	0.0520 (8)	0.0823 (11)	0.0020 (7)	0.0229 (8)	0.0108 (7)
C3A	0.0684 (9)	0.0642 (9)	0.0658 (8)	0.0038 (7)	0.0296 (7)	0.0035 (7)
C3B	0.0655 (8)	0.0583 (8)	0.0529 (7)	−0.0016 (6)	0.0198 (6)	0.0012 (6)
C4A	0.0510 (7)	0.0567 (7)	0.0545 (7)	0.0052 (5)	0.0206 (5)	−0.0041 (6)
C4B	0.0503 (7)	0.0485 (6)	0.0479 (6)	−0.0037 (5)	0.0177 (5)	−0.0059 (5)
C5A	0.0621 (8)	0.0589 (8)	0.0583 (7)	0.0040 (6)	0.0300 (6)	−0.0012 (6)
C5B	0.0589 (7)	0.0498 (7)	0.0467 (6)	−0.0028 (6)	0.0162 (5)	−0.0021 (5)
C6A	0.0596 (8)	0.0576 (8)	0.0566 (7)	0.0014 (6)	0.0292 (6)	−0.0011 (6)
C6B	0.0618 (8)	0.0496 (7)	0.0464 (6)	−0.0004 (6)	0.0180 (6)	−0.0015 (5)
C7A	0.0566 (7)	0.0571 (8)	0.0500 (6)	0.0053 (6)	0.0241 (6)	0.0033 (5)
C7B	0.0553 (7)	0.0517 (7)	0.0456 (6)	−0.0031 (5)	0.0191 (5)	−0.0004 (5)
C8A	0.0530 (7)	0.0533 (7)	0.0460 (6)	0.0032 (5)	0.0212 (5)	0.0049 (5)
C8B	0.0521 (6)	0.0468 (6)	0.0429 (6)	−0.0003 (5)	0.0182 (5)	0.0027 (5)
C9A	0.0670 (8)	0.0551 (7)	0.0528 (7)	−0.0043 (6)	0.0216 (6)	0.0035 (6)
C9B	0.0622 (8)	0.0509 (7)	0.0513 (7)	0.0054 (6)	0.0240 (6)	0.0053 (5)
C10A	0.0831 (10)	0.0518 (8)	0.0535 (7)	0.0035 (7)	0.0197 (7)	−0.0035 (6)
C10B	0.0758 (9)	0.0470 (7)	0.0614 (8)	0.0017 (6)	0.0354 (7)	−0.0044 (6)
C11A	0.0778 (9)	0.0630 (9)	0.0545 (7)	0.0077 (7)	0.0305 (7)	−0.0049 (6)
C11B	0.0734 (9)	0.0584 (8)	0.0468 (7)	−0.0006 (6)	0.0234 (6)	−0.0073 (6)
O1A	0.0811 (7)	0.0600 (6)	0.0785 (7)	0.0029 (5)	0.0379 (6)	−0.0134 (5)
O1B	0.0800 (6)	0.0518 (5)	0.0562 (5)	−0.0017 (5)	0.0207 (5)	−0.0112 (4)
O2A	0.1283 (10)	0.0679 (7)	0.0945 (8)	−0.0034 (7)	0.0796 (8)	−0.0053 (6)
O2B	0.1134 (9)	0.0567 (6)	0.0461 (5)	0.0022 (6)	0.0131 (5)	−0.0001 (4)
O3A	0.0719 (6)	0.0543 (5)	0.0595 (5)	−0.0005 (4)	0.0364 (5)	−0.0004 (4)
O3B	0.0719 (6)	0.0501 (5)	0.0441 (4)	0.0055 (4)	0.0187 (4)	0.0025 (4)

Geometric parameters (Å, º)

C1A—C2A	1.329 (3)	C6A—H6A	0.946 (16)
C1A—O1A	1.356 (2)	C6B—C7B	1.3264 (18)
C1A—H1A	0.99 (2)	C6B—H6B	0.974 (15)
C1B—C2B	1.321 (2)	C7A—C8A	1.4285 (18)
C1B—O1B	1.3575 (18)	C7A—H7A	0.954 (15)
C1B—H1B	0.96 (2)	C7B—C8B	1.4283 (17)
C2A—C3A	1.409 (2)	C7B—H7B	0.953 (15)
C2A—H2A	0.92 (2)	C8A—C9A	1.3458 (19)
C2B—C3B	1.413 (2)	C8A—O3A	1.3766 (15)
C2B—H2B	0.912 (19)	C8B—C9B	1.3523 (18)
C3A—C4A	1.348 (2)	C8B—O3B	1.3721 (14)
C3A—H3A	0.902 (16)	C9A—C10A	1.413 (2)
C3B—C4B	1.3456 (18)	C9A—H9A	0.970 (16)
C3B—H3B	0.896 (16)	C9B—C10B	1.4099 (19)
C4A—O1A	1.3641 (16)	C9B—H9B	0.956 (15)
C4A—C5A	1.456 (2)	C10A—C11A	1.327 (2)
C4B—O1B	1.3642 (15)	C10A—H10A	0.916 (17)
C4B—C5B	1.4586 (18)	C10B—C11B	1.329 (2)
C5A—O2A	1.2261 (16)	C10B—H10B	0.967 (16)
C5A—C6A	1.4641 (18)	C11A—O3A	1.3651 (16)
C5B—O2B	1.2216 (15)	C11A—H11A	0.937 (17)
C5B—C6B	1.4667 (17)	C11B—O3B	1.3640 (16)
C6A—C7A	1.3270 (19)	C11B—H11B	0.953 (16)
C2A—C1A—O1A	111.03 (15)	C5B—C6B—H6B	117.2 (9)
C2A—C1A—H1A	135.8 (12)	C6A—C7A—C8A	127.21 (12)
O1A—C1A—H1A	113.1 (12)	C6A—C7A—H7A	119.3 (9)
C2B—C1B—O1B	111.03 (14)	C8A—C7A—H7A	113.5 (9)
C2B—C1B—H1B	135.6 (12)	C6B—C7B—C8B	127.90 (12)
O1B—C1B—H1B	113.3 (12)	C6B—C7B—H7B	118.8 (9)
C1A—C2A—C3A	106.55 (16)	C8B—C7B—H7B	113.3 (9)
C1A—C2A—H2A	127.4 (12)	C9A—C8A—O3A	109.53 (11)
C3A—C2A—H2A	126.1 (12)	C9A—C8A—C7A	132.38 (12)
C1B—C2B—C3B	106.68 (14)	O3A—C8A—C7A	118.09 (11)
C1B—C2B—H2B	125.9 (12)	C9B—C8B—O3B	109.39 (11)
C3B—C2B—H2B	127.4 (12)	C9B—C8B—C7B	132.00 (12)
C4A—C3A—C2A	106.60 (15)	O3B—C8B—C7B	118.61 (11)
C4A—C3A—H3A	126.4 (10)	C8A—C9A—C10A	107.21 (13)
C2A—C3A—H3A	126.8 (10)	C8A—C9A—H9A	126.4 (9)
C4B—C3B—C2B	106.52 (13)	C10A—C9A—H9A	126.4 (9)
C4B—C3B—H3B	126.2 (10)	C8B—C9B—C10B	107.20 (12)
C2B—C3B—H3B	127.2 (10)	C8B—C9B—H9B	125.6 (9)
C3A—C4A—O1A	109.80 (13)	C10B—C9B—H9B	127.2 (9)
C3A—C4A—C5A	132.96 (13)	C11A—C10A—C9A	106.29 (13)
O1A—C4A—C5A	117.17 (12)	C11A—C10A—H10A	126.5 (10)
C3B—C4B—O1B	109.71 (12)	C9A—C10A—H10A	127.2 (10)
C3B—C4B—C5B	133.90 (12)	C11B—C10B—C9B	106.24 (12)
O1B—C4B—C5B	116.38 (11)	C11B—C10B—H10B	126.4 (9)
O2A—C5A—C4A	121.30 (12)	C9B—C10B—H10B	127.4 (9)
O2A—C5A—C6A	122.24 (13)	C10A—C11A—O3A	111.42 (13)
C4A—C5A—C6A	116.46 (12)	C10A—C11A—H11A	133.3 (10)
O2B—C5B—C4B	120.97 (11)	O3A—C11A—H11A	115.3 (10)
O2B—C5B—C6B	122.21 (12)	C10B—C11B—O3B	111.42 (12)
C4B—C5B—C6B	116.82 (11)	C10B—C11B—H11B	133.9 (10)
C7A—C6A—C5A	121.12 (13)	O3B—C11B—H11B	114.7 (10)
C7A—C6A—H6A	121.5 (9)	C1A—O1A—C4A	106.01 (13)
C5A—C6A—H6A	117.3 (9)	C1B—O1B—C4B	106.06 (11)
C7B—C6B—C5B	120.37 (12)	C11A—O3A—C8A	105.55 (11)
C7B—C6B—H6B	122.5 (9)	C11B—O3B—C8B	105.75 (10)
O1A—C1A—C2A—C3A	−0.8 (2)	C6A—C7A—C8A—O3A	−1.7 (2)
O1B—C1B—C2B—C3B	−0.1 (2)	C6B—C7B—C8B—C9B	−178.62 (15)
C1A—C2A—C3A—C4A	0.6 (2)	C6B—C7B—C8B—O3B	1.1 (2)
C1B—C2B—C3B—C4B	0.19 (19)	O3A—C8A—C9A—C10A	0.39 (15)
C2A—C3A—C4A—O1A	−0.22 (17)	C7A—C8A—C9A—C10A	−179.84 (14)
C2A—C3A—C4A—C5A	−177.22 (15)	O3B—C8B—C9B—C10B	−0.30 (15)
C2B—C3B—C4B—O1B	−0.18 (16)	C7B—C8B—C9B—C10B	179.44 (13)
C2B—C3B—C4B—C5B	177.97 (15)	C8A—C9A—C10A—C11A	−0.31 (17)
C3A—C4A—C5A—O2A	177.09 (16)	C8B—C9B—C10B—C11B	0.27 (16)
O1A—C4A—C5A—O2A	0.3 (2)	C9A—C10A—C11A—O3A	0.11 (18)
C3A—C4A—C5A—C6A	−2.6 (2)	C9B—C10B—C11B—O3B	−0.14 (17)
O1A—C4A—C5A—C6A	−179.45 (12)	C2A—C1A—O1A—C4A	0.67 (19)
C3B—C4B—C5B—O2B	−174.04 (15)	C3A—C4A—O1A—C1A	−0.25 (16)
O1B—C4B—C5B—O2B	4.02 (19)	C5A—C4A—O1A—C1A	177.27 (13)
C3B—C4B—C5B—C6B	6.0 (2)	C2B—C1B—O1B—C4B	0.02 (18)
O1B—C4B—C5B—C6B	−175.96 (11)	C3B—C4B—O1B—C1B	0.10 (16)
O2A—C5A—C6A—C7A	−6.6 (2)	C5B—C4B—O1B—C1B	−178.41 (12)
C4A—C5A—C6A—C7A	173.12 (13)	C10A—C11A—O3A—C8A	0.12 (16)
O2B—C5B—C6B—C7B	6.9 (2)	C9A—C8A—O3A—C11A	−0.32 (14)
C4B—C5B—C6B—C7B	−173.10 (12)	C7A—C8A—O3A—C11A	179.87 (11)
C5A—C6A—C7A—C8A	−179.34 (12)	C10B—C11B—O3B—C8B	−0.04 (16)
C5B—C6B—C7B—C8B	179.39 (12)	C9B—C8B—O3B—C11B	0.22 (14)
C6A—C7A—C8A—C9A	178.52 (15)	C7B—C8B—O3B—C11B	−179.56 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1B—H1B···O3B^i	0.96 (2)	2.56 (2)	3.4812 (19)	161.7 (16)
C9A—H9A···O2A^ii	0.970 (16)	2.474 (16)	3.4402 (18)	174.4 (13)
C9B—H9B···O2B^iii	0.956 (15)	2.507 (16)	3.4596 (17)	174.2 (12)
C10B—H10B···O2B^iv	0.967 (16)	2.528 (17)	3.4786 (17)	167.6 (12)
C11A—H11A···Cg4^v	0.937 (17)	2.837 (19)	3.5765 (19)	136.67 (13)
C11B—H11B···Cg3^vi	0.953 (16)	2.838 (17)	3.6160 (17)	139.53 (14)

Symmetry codes: (i) x, −y+1/2, z−1/2; (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, y−1, z; (vi) x, −y−1/2, z−1/2.