(2E,6E)-2,6-Difurfurylidenecyclo-hexa-none.

The complete mol-ecule of the title compound, C(16)H(14)O(3), is generated by crystallographic mirror symmetry, with two C atoms and one O atom lying on the mirror plane. The mol-ecule adopts an E configuration about the C=C bond and the dihedral angle between the furan rings is 16.1 (2)°.

Related literature

For general background to the use of bis­(aryl­methyl­idene)cyclo­alkanones as building blocks for the synthesis of biologically active heterocycles, see: Guilford et al. (1999 ▶). For related structures, see: Liu & Chen (2009 ▶); Liu (2009 ▶); Shi et al. (2008 ▶).

Experimental

Crystal data

C16H14O3

M = 254.27

Orthorhombic,

a = 7.7313 (11) Å

b = 15.658 (2) Å

c = 10.3388 (14) Å

V = 1251.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.15 × 0.10 × 0.06 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.995

6025 measured reflections

1158 independent reflections

731 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 1.03

1158 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904728X/hb5212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904728X/hb5212Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14O3	Dx = 1.349 Mg m−3
Mr = 254.27	Melting point: 417 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 472 reflections
a = 7.7313 (11) Å	θ = 2.6–19.2°
b = 15.658 (2) Å	µ = 0.09 mm−1
c = 10.3388 (14) Å	T = 295 K
V = 1251.5 (3) Å3	Block, yellow
Z = 4	0.15 × 0.10 × 0.06 mm
F(000) = 536

Siemens SMART CCD diffractometer	1158 independent reflections
Radiation source: fine-focus sealed tube	731 reflections with I > 2σ(I)
graphite	Rint = 0.072
ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.986, Tmax = 0.995	k = −15→18
6025 measured reflections	l = −12→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2592P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1158 reflections	Δρmax = 0.17 e Å−3
92 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

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
O1	0.0245 (3)	0.7500	0.0550 (2)	0.0606 (7)
O2	0.1187 (2)	0.44953 (11)	0.12636 (15)	0.0689 (6)
C1	0.0568 (4)	0.7500	0.1720 (3)	0.0461 (8)
C2	0.0806 (3)	0.66875 (14)	0.24340 (19)	0.0434 (6)
C3	0.0950 (3)	0.67029 (14)	0.3886 (2)	0.0509 (7)
H3A	0.2160	0.6668	0.4129	0.061*
H3B	0.0367	0.6206	0.4239	0.061*
C4	0.0172 (4)	0.7500	0.4467 (3)	0.0527 (9)
H4A	0.0366	0.7500	0.5394	0.063*
H4B	−0.1067	0.7500	0.4319	0.063*
C5	0.0954 (3)	0.59655 (14)	0.1739 (2)	0.0494 (6)
H5	0.0794	0.6022	0.0852	0.059*
C6	0.1324 (3)	0.51243 (15)	0.2189 (2)	0.0497 (7)
C7	0.1845 (4)	0.47563 (15)	0.3310 (2)	0.0602 (7)
H7	0.2048	0.5036	0.4089	0.072*
C8	0.2024 (4)	0.38729 (16)	0.3081 (2)	0.0646 (8)
H8	0.2366	0.3460	0.3674	0.078*
C9	0.1606 (4)	0.37468 (17)	0.1841 (3)	0.0729 (9)
H9	0.1603	0.3218	0.1432	0.087*

	U11	U22	U33	U12	U13	U23
O1	0.0879 (19)	0.0532 (15)	0.0406 (13)	0.000	−0.0145 (12)	0.000
O2	0.1102 (16)	0.0485 (11)	0.0481 (10)	0.0097 (10)	0.0021 (10)	−0.0052 (8)
C1	0.051 (2)	0.051 (2)	0.0365 (17)	0.000	−0.0044 (15)	0.000
C2	0.0445 (14)	0.0456 (14)	0.0402 (12)	−0.0018 (11)	−0.0005 (10)	−0.0007 (11)
C3	0.0656 (17)	0.0479 (14)	0.0391 (12)	−0.0026 (13)	−0.0014 (11)	0.0010 (11)
C4	0.061 (2)	0.059 (2)	0.0387 (17)	0.000	0.0036 (16)	0.000
C5	0.0538 (15)	0.0524 (16)	0.0421 (13)	−0.0002 (12)	−0.0027 (11)	0.0021 (11)
C6	0.0596 (17)	0.0451 (14)	0.0445 (13)	−0.0001 (12)	0.0003 (11)	−0.0024 (11)
C7	0.0767 (19)	0.0525 (16)	0.0513 (14)	−0.0008 (14)	−0.0073 (13)	−0.0004 (12)
C8	0.081 (2)	0.0479 (16)	0.0650 (17)	0.0033 (14)	0.0018 (15)	0.0110 (13)
C9	0.109 (2)	0.0432 (16)	0.0669 (18)	0.0100 (16)	0.0138 (17)	0.0018 (14)

O1—C1	1.235 (3)	C4—H4A	0.9700
O2—C9	1.355 (3)	C4—H4B	0.9700
O2—C6	1.377 (2)	C5—C6	1.426 (3)
C1—C2i	1.482 (3)	C5—H5	0.9300
C1—C2	1.482 (3)	C6—C7	1.355 (3)
C2—C5	1.344 (3)	C7—C8	1.410 (3)
C2—C3	1.506 (3)	C7—H7	0.9300
C3—C4	1.510 (3)	C8—C9	1.336 (3)
C3—H3A	0.9700	C8—H8	0.9300
C3—H3B	0.9700	C9—H9	0.9300
C4—C3i	1.510 (3)
C9—O2—C6	107.08 (19)	C3i—C4—H4B	109.3
O1—C1—C2i	120.85 (13)	H4A—C4—H4B	108.0
O1—C1—C2	120.85 (13)	C2—C5—C6	128.3 (2)
C2i—C1—C2	118.2 (3)	C2—C5—H5	115.9
C5—C2—C1	117.8 (2)	C6—C5—H5	115.9
C5—C2—C3	122.7 (2)	C7—C6—O2	108.2 (2)
C1—C2—C3	119.5 (2)	C7—C6—C5	137.0 (2)
C2—C3—C4	112.3 (2)	O2—C6—C5	114.73 (19)
C2—C3—H3A	109.1	C6—C7—C8	107.6 (2)
C4—C3—H3A	109.1	C6—C7—H7	126.2
C2—C3—H3B	109.1	C8—C7—H7	126.2
C4—C3—H3B	109.1	C9—C8—C7	106.4 (2)
H3A—C3—H3B	107.9	C9—C8—H8	126.8
C3—C4—C3i	111.5 (3)	C7—C8—H8	126.8
C3—C4—H4A	109.3	C8—C9—O2	110.7 (2)
C3i—C4—H4A	109.3	C8—C9—H9	124.7
C3—C4—H4B	109.3	O2—C9—H9	124.7
O1—C1—C2—C5	11.1 (4)	C9—O2—C6—C7	0.9 (3)
C2i—C1—C2—C5	−166.16 (18)	C9—O2—C6—C5	179.0 (2)
O1—C1—C2—C3	−171.5 (3)	C2—C5—C6—C7	−10.1 (5)
C2i—C1—C2—C3	11.2 (4)	C2—C5—C6—O2	172.5 (2)
C5—C2—C3—C4	−161.0 (2)	O2—C6—C7—C8	−0.5 (3)
C1—C2—C3—C4	21.8 (3)	C5—C6—C7—C8	−178.0 (3)
C2—C3—C4—C3i	−55.1 (3)	C6—C7—C8—C9	0.0 (3)
C1—C2—C5—C6	174.6 (2)	C7—C8—C9—O2	0.6 (3)
C3—C2—C5—C6	−2.7 (4)	C6—O2—C9—C8	−0.9 (3)