(3Z,3'Z)-3,3'-(3,5-Dimethyl-furan-2,4-diyl)bis-(4-hy-droxy-pent-3-en-2-one).

In the title mol-ecule, C(16)H(20)O(5), the two 4-hy-droxy-pent-3-en-2-one units are essentially planar, with r.m.s. deviations of 0.0183 (2) and 0.0134 (2) Å for the non-H atoms, and make dihedral angles of 81.20 (10) and 84.44 (10)° with the central furan ring. The dihedral angle between these two side units is 22.06 (9)°. Two intra-molecular O-H⋯O hydrogen bonds generate two S(6) ring motifs. A weak inter-molecular C-H⋯O inter-action is also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications of heterocyclic compounds, see: Abdel-Hamid et al. (2011 ▶); Alqasoumi et al. (2010 ▶); Al-Said et al. (2010 ▶, 2011 ▶); Ghorab et al. (2001 ▶); Ghorab, Al-Said & El-Hossary (2011 ▶); Ghorab, Ragab et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C16H20O5

M = 292.32

Triclinic,

a = 7.2645 (2) Å

b = 8.5771 (2) Å

c = 13.0931 (5) Å

α = 88.384 (2)°

β = 76.390 (2)°

γ = 87.814 (1)°

V = 792.17 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.75 mm−1

T = 296 K

0.59 × 0.55 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.665, T max = 0.868

6643 measured reflections

2597 independent reflections

2344 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.170

S = 1.04

2597 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007696/is5075sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007696/is5075Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007696/is5075Isup3.cml

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

C16H20O5	Z = 2
Mr = 292.32	F(000) = 312
Triclinic, P1	Dx = 1.226 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.2645 (2) Å	Cell parameters from 2597 reflections
b = 8.5771 (2) Å	θ = 5.2–65.0°
c = 13.0931 (5) Å	µ = 0.75 mm−1
α = 88.384 (2)°	T = 296 K
β = 76.390 (2)°	Block, colorless
γ = 87.814 (1)°	0.59 × 0.55 × 0.19 mm
V = 792.17 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2597 independent reflections
Radiation source: fine-focus sealed tube	2344 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 65.0°, θmin = 5.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→7
Tmin = 0.665, Tmax = 0.868	k = −10→10
6643 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.104P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max = 0.001
196 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.02411 (17)	0.56371 (13)	0.31031 (9)	0.0579 (4)
O2	0.2498 (3)	0.88634 (18)	0.05070 (13)	0.0854 (5)
O3	0.5019 (2)	0.8614 (2)	0.14714 (14)	0.0912 (5)
H3A	0.4399	0.8966	0.1064	0.137*
O4	0.1552 (3)	−0.08978 (17)	0.39756 (13)	0.0854 (5)
O5	−0.0968 (2)	−0.09275 (16)	0.29980 (13)	0.0825 (5)
H5A	−0.0240	−0.1262	0.3351	0.124*
C1	0.1759 (3)	0.5388 (2)	0.22504 (14)	0.0547 (4)
C2	0.2125 (2)	0.38426 (19)	0.21246 (13)	0.0538 (4)
C3	0.0787 (2)	0.30746 (19)	0.29583 (13)	0.0508 (4)
C4	−0.0310 (3)	0.4202 (2)	0.35119 (14)	0.0538 (4)
C5	0.2626 (3)	0.6793 (2)	0.16975 (14)	0.0583 (5)
C6	0.1785 (3)	0.7605 (2)	0.09731 (15)	0.0663 (5)
C7	0.0029 (4)	0.7092 (3)	0.0709 (2)	0.0870 (7)
H7A	−0.0877	0.7950	0.0782	0.131*
H7B	−0.0491	0.6254	0.1177	0.131*
H7C	0.0318	0.6739	−0.0002	0.131*
C8	0.4249 (3)	0.7383 (2)	0.19331 (17)	0.0690 (5)
C9	0.5166 (3)	0.6632 (3)	0.2732 (2)	0.0892 (7)
H9A	0.6096	0.7309	0.2872	0.134*
H9B	0.5770	0.5661	0.2470	0.134*
H9C	0.4224	0.6442	0.3368	0.134*
C10	0.3607 (3)	0.3067 (3)	0.12838 (17)	0.0742 (6)
H10A	0.4233	0.3843	0.0795	0.111*
H10B	0.3021	0.2346	0.0921	0.111*
H10C	0.4518	0.2516	0.1596	0.111*
C11	0.0602 (3)	0.13679 (19)	0.31678 (13)	0.0547 (4)
C12	0.1725 (3)	0.0557 (2)	0.37746 (15)	0.0659 (5)
C13	0.3133 (4)	0.1371 (3)	0.4210 (2)	0.0940 (8)
H13A	0.3939	0.0613	0.4460	0.141*
H13B	0.2482	0.2012	0.4780	0.141*
H13C	0.3887	0.2012	0.3669	0.141*
C14	−0.0705 (3)	0.0548 (2)	0.27961 (15)	0.0632 (5)
C15	−0.1914 (4)	0.1271 (3)	0.2129 (2)	0.0890 (7)
H15A	−0.2962	0.0616	0.2140	0.134*
H15B	−0.1179	0.1386	0.1420	0.134*
H15C	−0.2383	0.2277	0.2395	0.134*
C16	−0.1966 (3)	0.4172 (2)	0.44325 (16)	0.0697 (6)
H16A	−0.2166	0.3117	0.4688	0.105*
H16B	−0.3075	0.4577	0.4224	0.105*
H16C	−0.1724	0.4801	0.4979	0.105*

	U11	U22	U33	U12	U13	U23
O1	0.0659 (8)	0.0415 (6)	0.0592 (7)	−0.0044 (5)	−0.0001 (6)	0.0031 (5)
O2	0.1097 (12)	0.0637 (9)	0.0794 (10)	−0.0191 (8)	−0.0158 (9)	0.0265 (7)
O3	0.0894 (11)	0.0805 (11)	0.1025 (12)	−0.0404 (9)	−0.0176 (9)	0.0250 (9)
O4	0.1135 (13)	0.0554 (9)	0.0822 (10)	0.0142 (8)	−0.0179 (9)	0.0180 (7)
O5	0.1042 (12)	0.0466 (8)	0.0954 (11)	−0.0176 (7)	−0.0198 (9)	0.0084 (7)
C1	0.0564 (10)	0.0486 (9)	0.0544 (9)	−0.0075 (7)	−0.0030 (7)	0.0045 (7)
C2	0.0551 (9)	0.0474 (9)	0.0555 (9)	−0.0046 (7)	−0.0065 (7)	0.0054 (7)
C3	0.0552 (9)	0.0426 (9)	0.0536 (9)	−0.0053 (7)	−0.0105 (7)	0.0059 (7)
C4	0.0601 (10)	0.0446 (9)	0.0537 (9)	−0.0077 (7)	−0.0071 (7)	0.0064 (7)
C5	0.0633 (11)	0.0469 (9)	0.0587 (10)	−0.0095 (8)	−0.0013 (8)	0.0044 (7)
C6	0.0791 (13)	0.0561 (11)	0.0582 (11)	−0.0090 (9)	−0.0047 (9)	0.0049 (8)
C7	0.0965 (17)	0.0908 (17)	0.0779 (14)	−0.0173 (13)	−0.0279 (12)	0.0123 (12)
C8	0.0658 (12)	0.0605 (11)	0.0736 (12)	−0.0148 (9)	−0.0010 (9)	0.0074 (9)
C9	0.0727 (14)	0.0967 (18)	0.0993 (17)	−0.0199 (13)	−0.0222 (12)	0.0210 (14)
C10	0.0751 (13)	0.0631 (12)	0.0720 (13)	0.0052 (10)	0.0058 (10)	0.0032 (9)
C11	0.0643 (10)	0.0420 (9)	0.0531 (9)	−0.0006 (7)	−0.0054 (7)	0.0060 (7)
C12	0.0771 (12)	0.0568 (11)	0.0590 (11)	0.0070 (9)	−0.0090 (9)	0.0088 (8)
C13	0.0952 (17)	0.0977 (18)	0.0954 (18)	−0.0016 (14)	−0.0378 (14)	0.0198 (14)
C14	0.0750 (12)	0.0458 (10)	0.0640 (11)	−0.0068 (8)	−0.0064 (9)	0.0040 (8)
C15	0.0996 (18)	0.0742 (15)	0.1048 (18)	−0.0193 (13)	−0.0461 (15)	0.0119 (13)
C16	0.0741 (13)	0.0586 (11)	0.0650 (11)	−0.0026 (9)	0.0056 (9)	0.0070 (9)

O1—C4	1.364 (2)	C8—C9	1.486 (3)
O1—C1	1.387 (2)	C9—H9A	0.9600
O2—C6	1.289 (2)	C9—H9B	0.9600
O3—C8	1.281 (2)	C9—H9C	0.9600
O3—H3A	0.8200	C10—H10A	0.9600
O4—C12	1.272 (2)	C10—H10B	0.9600
O5—C14	1.297 (2)	C10—H10C	0.9600
O5—H5A	0.8200	C11—C14	1.386 (3)
C1—C2	1.349 (2)	C11—C12	1.418 (3)
C1—C5	1.472 (2)	C12—C13	1.486 (3)
C2—C3	1.442 (2)	C13—H13A	0.9600
C2—C10	1.497 (2)	C13—H13B	0.9600
C3—C4	1.344 (2)	C13—H13C	0.9600
C3—C11	1.487 (2)	C14—C15	1.486 (3)
C4—C16	1.490 (2)	C15—H15A	0.9600
C5—C6	1.401 (3)	C15—H15B	0.9600
C5—C8	1.403 (3)	C15—H15C	0.9600
C6—C7	1.483 (3)	C16—H16A	0.9600
C7—H7A	0.9600	C16—H16B	0.9600
C7—H7B	0.9600	C16—H16C	0.9600
C7—H7C	0.9600
C4—O1—C1	106.75 (13)	H9B—C9—H9C	109.5
C8—O3—H3A	109.5	C2—C10—H10A	109.5
C14—O5—H5A	109.5	C2—C10—H10B	109.5
C2—C1—O1	109.76 (15)	H10A—C10—H10B	109.5
C2—C1—C5	133.94 (17)	C2—C10—H10C	109.5
O1—C1—C5	116.29 (15)	H10A—C10—H10C	109.5
C1—C2—C3	106.28 (15)	H10B—C10—H10C	109.5
C1—C2—C10	127.22 (17)	C14—C11—C12	118.74 (17)
C3—C2—C10	126.50 (16)	C14—C11—C3	120.62 (16)
C4—C3—C2	106.76 (15)	C12—C11—C3	120.62 (17)
C4—C3—C11	125.75 (16)	O4—C12—C11	121.2 (2)
C2—C3—C11	127.48 (15)	O4—C12—C13	117.37 (19)
C3—C4—O1	110.43 (15)	C11—C12—C13	121.47 (19)
C3—C4—C16	132.98 (16)	C12—C13—H13A	109.5
O1—C4—C16	116.57 (15)	C12—C13—H13B	109.5
C6—C5—C8	119.11 (17)	H13A—C13—H13B	109.5
C6—C5—C1	120.53 (17)	C12—C13—H13C	109.5
C8—C5—C1	120.27 (17)	H13A—C13—H13C	109.5
O2—C6—C5	121.16 (19)	H13B—C13—H13C	109.5
O2—C6—C7	116.34 (19)	O5—C14—C11	122.60 (19)
C5—C6—C7	122.50 (18)	O5—C14—C15	114.18 (19)
C6—C7—H7A	109.5	C11—C14—C15	123.22 (17)
C6—C7—H7B	109.5	C14—C15—H15A	109.5
H7A—C7—H7B	109.5	C14—C15—H15B	109.5
C6—C7—H7C	109.5	H15A—C15—H15B	109.5
H7A—C7—H7C	109.5	C14—C15—H15C	109.5
H7B—C7—H7C	109.5	H15A—C15—H15C	109.5
O3—C8—C5	121.5 (2)	H15B—C15—H15C	109.5
O3—C8—C9	116.2 (2)	C4—C16—H16A	109.5
C5—C8—C9	122.28 (18)	C4—C16—H16B	109.5
C8—C9—H9A	109.5	H16A—C16—H16B	109.5
C8—C9—H9B	109.5	C4—C16—H16C	109.5
H9A—C9—H9B	109.5	H16A—C16—H16C	109.5
C8—C9—H9C	109.5	H16B—C16—H16C	109.5
H9A—C9—H9C	109.5
C4—O1—C1—C2	0.7 (2)	C8—C5—C6—O2	1.4 (3)
C4—O1—C1—C5	−178.48 (15)	C1—C5—C6—O2	177.88 (17)
O1—C1—C2—C3	−1.2 (2)	C8—C5—C6—C7	−177.8 (2)
C5—C1—C2—C3	177.8 (2)	C1—C5—C6—C7	−1.2 (3)
O1—C1—C2—C10	178.20 (18)	C6—C5—C8—O3	−2.7 (3)
C5—C1—C2—C10	−2.8 (4)	C1—C5—C8—O3	−179.23 (18)
C1—C2—C3—C4	1.2 (2)	C6—C5—C8—C9	176.9 (2)
C10—C2—C3—C4	−178.19 (19)	C1—C5—C8—C9	0.4 (3)
C1—C2—C3—C11	−179.96 (17)	C4—C3—C11—C14	82.7 (2)
C10—C2—C3—C11	0.6 (3)	C2—C3—C11—C14	−95.9 (2)
C2—C3—C4—O1	−0.8 (2)	C4—C3—C11—C12	−95.7 (2)
C11—C3—C4—O1	−179.63 (15)	C2—C3—C11—C12	85.7 (2)
C2—C3—C4—C16	177.7 (2)	C14—C11—C12—O4	0.2 (3)
C11—C3—C4—C16	−1.1 (3)	C3—C11—C12—O4	178.64 (17)
C1—O1—C4—C3	0.1 (2)	C14—C11—C12—C13	−179.13 (19)
C1—O1—C4—C16	−178.72 (17)	C3—C11—C12—C13	−0.7 (3)
C2—C1—C5—C6	101.3 (3)	C12—C11—C14—O5	1.4 (3)
O1—C1—C5—C6	−79.7 (2)	C3—C11—C14—O5	−177.04 (17)
C2—C1—C5—C8	−82.2 (3)	C12—C11—C14—C15	−178.23 (19)
O1—C1—C5—C8	96.8 (2)	C3—C11—C14—C15	3.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.71	2.457 (3)	150
O5—H5A···O4	0.82	1.73	2.470 (3)	148
C15—H15A···O3i	0.96	2.60	3.507 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2	0.82	1.71	2.457 (3)	150
O5—H5A⋯O4	0.82	1.73	2.470 (3)	148
C15—H15A⋯O3i	0.96	2.60	3.507 (3)	158

Symmetry code: (i) .