(2E,5E)-2,5-Difurfurylidenecyclo-penta-none.

In the title mol-ecule, C(15)H(12)O(3), the three five-membered rings are nearly coplanar: the dihedral angles between the cyclopentanone ring and the furan rings are 3.5 (2) and 9.7 (2)°, and the two furan rings form a dihedral angle of 7.2 (2)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds help to consolidate the crystal packing.

Related literature

For 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: Du et al. (2007 ▶); Sun & Cui (2007 ▶); Wei et al. (2008 ▶).

Experimental

Crystal data

C15H12O3

M = 240.25

Monoclinic,

a = 5.9280 (9) Å

b = 8.5031 (13) Å

c = 23.280 (3) Å

β = 92.139 (3)°

V = 1172.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.12 × 0.08 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.989, T max = 0.995

5793 measured reflections

2076 independent reflections

1083 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.129

S = 0.99

2076 reflections

164 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/S1600536809047278/cv2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047278/cv2656Isup2.hkl

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

C15H12O3	F(000) = 504
Mr = 240.25	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Melting point: 405 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.9280 (9) Å	Cell parameters from 461 reflections
b = 8.5031 (13) Å	θ = 3.0–18.7°
c = 23.280 (3) Å	µ = 0.10 mm−1
β = 92.139 (3)°	T = 298 K
V = 1172.6 (3) Å3	Block, yellow
Z = 4	0.12 × 0.08 × 0.05 mm

Bruker SMART CCD area-detector diffractometer	2076 independent reflections
Radiation source: fine-focus sealed tube	1083 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.989, Tmax = 0.995	k = −10→9
5793 measured reflections	l = −27→19

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2076 reflections	Δρmax = 0.17 e Å−3
164 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: 0.015 (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	1.2374 (3)	0.2225 (2)	0.62045 (7)	0.0606 (6)
O2	1.3568 (3)	0.4626 (2)	0.42876 (8)	0.0648 (6)
O3	0.7570 (3)	−0.1375 (2)	0.73472 (8)	0.0640 (6)
C1	1.0690 (5)	0.1894 (3)	0.58984 (11)	0.0443 (7)
C2	1.0293 (4)	0.2376 (3)	0.52998 (10)	0.0416 (7)
C3	0.8083 (4)	0.1745 (3)	0.50780 (10)	0.0496 (7)
H3A	0.8296	0.1048	0.4755	0.059*
H3B	0.7091	0.2597	0.4954	0.059*
C4	0.7065 (4)	0.0834 (3)	0.55845 (10)	0.0487 (7)
H4A	0.5655	0.1311	0.5692	0.058*
H4B	0.6780	−0.0252	0.5478	0.058*
C5	0.8774 (4)	0.0925 (3)	0.60707 (11)	0.0430 (7)
C6	1.1804 (4)	0.3239 (3)	0.50282 (11)	0.0476 (7)
H6	1.3098	0.3508	0.5244	0.057*
C7	1.1698 (5)	0.3802 (3)	0.44512 (12)	0.0459 (7)
C8	1.0169 (5)	0.3795 (3)	0.40086 (12)	0.0569 (8)
H8	0.8755	0.3320	0.4004	0.068*
C9	1.1100 (6)	0.4640 (3)	0.35521 (12)	0.0652 (9)
H9	1.0427	0.4831	0.3192	0.078*
C10	1.3128 (6)	0.5103 (4)	0.37419 (13)	0.0704 (10)
H10	1.4122	0.5684	0.3526	0.084*
C11	0.8754 (4)	0.0258 (3)	0.65893 (11)	0.0499 (7)
H11	1.0011	0.0448	0.6830	0.060*
C12	0.7047 (5)	−0.0711 (3)	0.68205 (11)	0.0465 (7)
C13	0.4940 (5)	−0.1134 (3)	0.66577 (12)	0.0579 (8)
H13	0.4170	−0.0844	0.6319	0.069*
C14	0.4101 (5)	−0.2101 (4)	0.70957 (13)	0.0657 (9)
H14	0.2682	−0.2566	0.7101	0.079*
C15	0.5736 (5)	−0.2212 (4)	0.74968 (13)	0.0642 (9)
H15	0.5640	−0.2786	0.7835	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0480 (12)	0.0831 (16)	0.0497 (12)	−0.0054 (11)	−0.0089 (9)	0.0018 (10)
O2	0.0632 (13)	0.0725 (15)	0.0587 (14)	−0.0127 (11)	0.0024 (10)	0.0110 (11)
O3	0.0670 (14)	0.0815 (16)	0.0430 (12)	−0.0039 (12)	−0.0042 (10)	0.0100 (10)
C1	0.0404 (16)	0.0489 (18)	0.0437 (17)	0.0062 (14)	0.0016 (13)	−0.0033 (13)
C2	0.0419 (16)	0.0414 (17)	0.0413 (16)	0.0049 (13)	0.0006 (12)	−0.0041 (12)
C3	0.0478 (17)	0.0550 (19)	0.0456 (17)	0.0013 (14)	−0.0021 (13)	−0.0022 (13)
C4	0.0449 (17)	0.0526 (18)	0.0484 (17)	−0.0014 (14)	−0.0006 (13)	−0.0019 (13)
C5	0.0422 (16)	0.0451 (17)	0.0417 (17)	0.0039 (13)	0.0022 (13)	−0.0042 (13)
C6	0.0472 (17)	0.0489 (19)	0.0466 (17)	0.0040 (14)	−0.0018 (13)	−0.0021 (13)
C7	0.0457 (17)	0.0408 (17)	0.0515 (18)	−0.0017 (13)	0.0048 (14)	−0.0021 (13)
C8	0.059 (2)	0.059 (2)	0.0522 (19)	−0.0027 (15)	−0.0028 (16)	−0.0025 (15)
C9	0.090 (3)	0.062 (2)	0.0430 (19)	0.0013 (18)	−0.0044 (17)	0.0024 (16)
C10	0.094 (3)	0.064 (2)	0.054 (2)	−0.0035 (19)	0.0106 (19)	0.0113 (17)
C11	0.0482 (17)	0.058 (2)	0.0435 (17)	0.0025 (14)	−0.0019 (13)	−0.0027 (14)
C12	0.0539 (19)	0.0477 (18)	0.0377 (16)	0.0054 (15)	−0.0009 (13)	0.0013 (13)
C13	0.058 (2)	0.066 (2)	0.0493 (18)	−0.0032 (16)	−0.0052 (15)	0.0082 (15)
C14	0.061 (2)	0.078 (2)	0.058 (2)	−0.0164 (17)	0.0007 (17)	0.0083 (17)
C15	0.072 (2)	0.071 (2)	0.050 (2)	−0.0090 (19)	0.0120 (17)	0.0091 (16)

O1—C1	1.237 (3)	C6—C7	1.425 (3)
O2—C10	1.350 (3)	C6—H6	0.9300
O2—C7	1.377 (3)	C7—C8	1.347 (3)
O3—C15	1.356 (3)	C8—C9	1.412 (4)
O3—C12	1.375 (3)	C8—H8	0.9300
C1—C2	1.463 (3)	C9—C10	1.326 (4)
C1—C5	1.471 (3)	C9—H9	0.9300
C2—C6	1.335 (3)	C10—H10	0.9300
C2—C3	1.490 (3)	C11—C12	1.426 (4)
C3—C4	1.552 (3)	C11—H11	0.9300
C3—H3A	0.9700	C12—C13	1.341 (3)
C3—H3B	0.9700	C13—C14	1.415 (4)
C4—C5	1.493 (3)	C13—H13	0.9300
C4—H4A	0.9700	C14—C15	1.324 (3)
C4—H4B	0.9700	C14—H14	0.9300
C5—C11	1.335 (3)	C15—H15	0.9300
C10—O2—C7	106.5 (2)	C8—C7—C6	136.4 (3)
C15—O3—C12	106.8 (2)	O2—C7—C6	115.1 (2)
O1—C1—C2	125.6 (3)	C7—C8—C9	107.6 (3)
O1—C1—C5	125.8 (2)	C7—C8—H8	126.2
C2—C1—C5	108.6 (2)	C9—C8—H8	126.2
C6—C2—C1	121.2 (2)	C10—C9—C8	106.0 (3)
C6—C2—C3	129.1 (2)	C10—C9—H9	127.0
C1—C2—C3	109.7 (2)	C8—C9—H9	127.0
C2—C3—C4	106.2 (2)	C9—C10—O2	111.4 (3)
C2—C3—H3A	110.5	C9—C10—H10	124.3
C4—C3—H3A	110.5	O2—C10—H10	124.3
C2—C3—H3B	110.5	C5—C11—C12	128.1 (2)
C4—C3—H3B	110.5	C5—C11—H11	115.9
H3A—C3—H3B	108.7	C12—C11—H11	115.9
C5—C4—C3	106.2 (2)	C13—C12—O3	108.6 (2)
C5—C4—H4A	110.5	C13—C12—C11	135.6 (3)
C3—C4—H4A	110.5	O3—C12—C11	115.7 (2)
C5—C4—H4B	110.5	C12—C13—C14	107.5 (3)
C3—C4—H4B	110.5	C12—C13—H13	126.2
H4A—C4—H4B	108.7	C14—C13—H13	126.2
C11—C5—C1	121.2 (2)	C15—C14—C13	106.4 (3)
C11—C5—C4	129.4 (2)	C15—C14—H14	126.8
C1—C5—C4	109.3 (2)	C13—C14—H14	126.8
C2—C6—C7	128.6 (2)	C14—C15—O3	110.8 (3)
C2—C6—H6	115.7	C14—C15—H15	124.6
C7—C6—H6	115.7	O3—C15—H15	124.6
C8—C7—O2	108.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.93	2.49	3.221 (4)	136
C4—H4A···O1ii	0.97	2.45	3.393 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.93	2.49	3.221 (4)	136
C4—H4A⋯O1ii	0.97	2.45	3.393 (3)	165

Symmetry codes: (i) ; (ii) .