3-[4-(Benz-yloxy)phen-yl]-1-(2-fur-yl)-3-hydroxy-prop-2-en-1-one.

In the crystal structure of the title compound, C(20)H(16)O(4), which is in the enol form, the central benzene ring makes dihedral angles of 63.42 (9) and 5.19 (10)° with the phenyl and furan rings, respectively. There is a short strong intra-molecular O-H⋯O hydrogen bond.

Related literature

For hydrogen bonds in 1,3-diketones, see: Bertolasi et al. (1991 ▶); Gilli et al. (2004 ▶); Vila et al. (1991 ▶). For 1,3-diketones as ligands, see: Baskar & Roesky (2005 ▶); Bassett et al. (2004 ▶); Jang et al. (2006 ▶); Soldatov et al. (2003 ▶).

Experimental

Crystal data

C20H16O4

M = 320.33

Triclinic,

a = 5.8927 (6) Å

b = 11.3365 (11) Å

c = 13.3039 (13) Å

α = 112.111 (3)°

β = 96.687 (3)°

γ = 98.638 (3)°

V = 799.39 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.32 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.983

6611 measured reflections

3439 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.147

S = 0.95

3439 reflections

220 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536808036659/is2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036659/is2357Isup2.hkl

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

C20H16O4	Z = 2
Mr = 320.33	F000 = 336
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Melting point: 403 K
a = 5.8927 (6) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.3365 (11) Å	Cell parameters from 1997 reflections
c = 13.3039 (13) Å	θ = 3.1–26.1º
α = 112.111 (3)º	µ = 0.09 mm−1
β = 96.687 (3)º	T = 298 (2) K
γ = 98.638 (3)º	Block, yellow
V = 799.39 (14) Å3	0.32 × 0.20 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	3439 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.078
T = 298(2) K	θmax = 27.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.978, Tmax = 0.983	k = −14→14
6611 measured reflections	l = −16→16

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
3439 reflections	Δρmax = 0.18 e Å−3
220 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	−0.1919 (3)	0.94140 (17)	−0.21175 (14)	0.0561 (4)
H1	−0.2852	0.9490	−0.1588	0.067*
C2	−0.2151 (3)	1.01001 (18)	−0.27760 (15)	0.0624 (5)
H2	−0.3229	1.0636	−0.2686	0.075*
C3	−0.0791 (3)	0.99904 (18)	−0.35624 (13)	0.0628 (5)
H3	−0.0943	1.0449	−0.4008	0.075*
C4	0.0791 (4)	0.9200 (2)	−0.36863 (14)	0.0707 (5)
H4	0.1716	0.9124	−0.4219	0.085*
C5	0.1021 (3)	0.85205 (18)	−0.30303 (14)	0.0625 (5)
H5	0.2100	0.7986	−0.3124	0.075*
C6	−0.0332 (3)	0.86224 (15)	−0.22321 (12)	0.0470 (4)
C7	−0.0042 (3)	0.78860 (17)	−0.15223 (14)	0.0543 (4)
H7A	−0.1266	0.7946	−0.1088	0.065*
H7B	−0.0133	0.6975	−0.1976	0.065*
C8	0.2985 (3)	0.78337 (14)	−0.01798 (12)	0.0437 (4)
C9	0.1650 (3)	0.67956 (17)	−0.00705 (15)	0.0572 (5)
H9	0.0099	0.6479	−0.0432	0.069*
C10	0.2624 (3)	0.62314 (17)	0.05756 (14)	0.0566 (5)
H10	0.1708	0.5530	0.0641	0.068*
C11	0.4923 (3)	0.66708 (14)	0.11326 (12)	0.0430 (4)
C12	0.6215 (3)	0.77425 (15)	0.10371 (12)	0.0487 (4)
H12	0.7755	0.8073	0.1413	0.058*
C13	0.5265 (3)	0.83230 (15)	0.04000 (13)	0.0493 (4)
H13	0.6155	0.9047	0.0357	0.059*
C14	0.5877 (3)	0.60034 (15)	0.17882 (12)	0.0459 (4)
C15	0.8145 (3)	0.63971 (16)	0.23933 (13)	0.0493 (4)
H15	0.9149	0.7099	0.2370	0.059*
C16	0.8939 (3)	0.57587 (17)	0.30329 (13)	0.0523 (4)
C17	1.1263 (3)	0.62181 (18)	0.37217 (13)	0.0561 (4)
C18	1.2389 (4)	0.5838 (2)	0.44496 (16)	0.0779 (6)
H18	1.1821	0.5149	0.4632	0.094*
C19	1.4595 (4)	0.6689 (3)	0.48793 (17)	0.0878 (7)
H19	1.5767	0.6671	0.5402	0.105*
C20	1.4681 (4)	0.7517 (2)	0.43989 (17)	0.0821 (7)
H20	1.5957	0.8185	0.4537	0.099*
O1	0.22079 (19)	0.84506 (10)	−0.08083 (9)	0.0549 (3)
O2	0.4480 (2)	0.49997 (11)	0.17879 (10)	0.0593 (3)
O3	0.7661 (2)	0.47547 (13)	0.30691 (11)	0.0682 (4)
O4	1.2673 (2)	0.72692 (13)	0.36792 (9)	0.0661 (4)
H2A	0.573 (4)	0.473 (2)	0.2360 (18)	0.099*

	U11	U22	U33	U12	U13	U23
C1	0.0612 (10)	0.0584 (11)	0.0545 (10)	0.0197 (8)	0.0132 (8)	0.0256 (9)
C2	0.0691 (11)	0.0551 (11)	0.0649 (11)	0.0249 (9)	0.0015 (9)	0.0249 (9)
C3	0.0835 (13)	0.0586 (11)	0.0460 (10)	0.0101 (10)	−0.0026 (9)	0.0268 (9)
C4	0.0881 (13)	0.0858 (15)	0.0494 (10)	0.0291 (11)	0.0207 (10)	0.0330 (10)
C5	0.0706 (11)	0.0704 (12)	0.0559 (10)	0.0315 (9)	0.0166 (9)	0.0281 (9)
C6	0.0533 (9)	0.0446 (9)	0.0408 (8)	0.0094 (7)	0.0023 (7)	0.0167 (7)
C7	0.0536 (9)	0.0518 (10)	0.0594 (10)	0.0085 (7)	0.0032 (8)	0.0277 (8)
C8	0.0538 (9)	0.0380 (8)	0.0411 (8)	0.0099 (7)	0.0076 (7)	0.0181 (7)
C9	0.0489 (9)	0.0528 (10)	0.0709 (11)	−0.0024 (7)	−0.0039 (8)	0.0354 (9)
C10	0.0540 (10)	0.0505 (10)	0.0702 (11)	−0.0013 (8)	0.0000 (8)	0.0375 (9)
C11	0.0491 (8)	0.0407 (8)	0.0413 (8)	0.0096 (7)	0.0095 (7)	0.0183 (7)
C12	0.0481 (9)	0.0494 (9)	0.0481 (9)	0.0015 (7)	0.0031 (7)	0.0239 (8)
C13	0.0536 (9)	0.0434 (9)	0.0515 (9)	−0.0011 (7)	0.0056 (7)	0.0251 (8)
C14	0.0568 (9)	0.0432 (9)	0.0421 (8)	0.0121 (7)	0.0144 (7)	0.0198 (7)
C15	0.0556 (9)	0.0494 (9)	0.0468 (9)	0.0114 (7)	0.0077 (7)	0.0239 (8)
C16	0.0633 (10)	0.0554 (11)	0.0463 (9)	0.0246 (8)	0.0171 (8)	0.0230 (8)
C17	0.0650 (10)	0.0659 (12)	0.0482 (10)	0.0312 (9)	0.0164 (8)	0.0267 (9)
C18	0.0854 (15)	0.1060 (17)	0.0697 (12)	0.0522 (13)	0.0222 (11)	0.0510 (12)
C19	0.0787 (15)	0.128 (2)	0.0584 (13)	0.0552 (14)	0.0019 (10)	0.0304 (13)
C20	0.0648 (12)	0.0965 (17)	0.0662 (13)	0.0287 (11)	−0.0040 (10)	0.0124 (12)
O1	0.0627 (7)	0.0467 (7)	0.0560 (7)	0.0009 (5)	−0.0054 (5)	0.0302 (6)
O2	0.0605 (7)	0.0568 (7)	0.0712 (8)	0.0060 (6)	0.0086 (6)	0.0408 (7)
O3	0.0772 (9)	0.0687 (9)	0.0799 (9)	0.0223 (7)	0.0166 (7)	0.0498 (7)
O4	0.0671 (8)	0.0683 (9)	0.0576 (8)	0.0189 (7)	0.0014 (6)	0.0208 (7)

C1—C6	1.373 (2)	C10—H10	0.9300
C1—C2	1.381 (2)	C11—C12	1.390 (2)
C1—H1	0.9300	C11—C14	1.469 (2)
C2—C3	1.371 (3)	C12—C13	1.373 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.369 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—O2	1.3000 (19)
C4—C5	1.373 (2)	C14—C15	1.391 (2)
C4—H4	0.9300	C15—C16	1.393 (2)
C5—C6	1.382 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—O3	1.287 (2)
C6—C7	1.489 (2)	C16—C17	1.456 (3)
C7—O1	1.4364 (19)	C17—C18	1.347 (2)
C7—H7A	0.9700	C17—O4	1.371 (2)
C7—H7B	0.9700	C18—C19	1.408 (3)
C8—O1	1.3583 (17)	C18—H18	0.9300
C8—C9	1.379 (2)	C19—C20	1.318 (3)
C8—C13	1.386 (2)	C19—H19	0.9300
C9—C10	1.374 (2)	C20—O4	1.352 (2)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.385 (2)	O2—H2A	1.15 (3)
C6—C1—C2	121.06 (16)	C10—C11—C14	119.56 (13)
C6—C1—H1	119.5	C12—C11—C14	123.34 (14)
C2—C1—H1	119.5	C13—C12—C11	121.39 (14)
C3—C2—C1	119.91 (17)	C13—C12—H12	119.3
C3—C2—H2	120.0	C11—C12—H12	119.3
C1—C2—H2	120.0	C12—C13—C8	120.24 (14)
C4—C3—C2	119.52 (16)	C12—C13—H13	119.9
C4—C3—H3	120.2	C8—C13—H13	119.9
C2—C3—H3	120.2	O2—C14—C15	119.95 (14)
C3—C4—C5	120.50 (17)	O2—C14—C11	116.68 (14)
C3—C4—H4	119.8	C15—C14—C11	123.37 (14)
C5—C4—H4	119.8	C14—C15—C16	121.14 (15)
C4—C5—C6	120.71 (17)	C14—C15—H15	119.4
C4—C5—H5	119.6	C16—C15—H15	119.4
C6—C5—H5	119.6	O3—C16—C15	122.40 (16)
C1—C6—C5	118.30 (15)	O3—C16—C17	116.31 (15)
C1—C6—C7	121.80 (15)	C15—C16—C17	121.28 (16)
C5—C6—C7	119.90 (15)	C18—C17—O4	109.43 (17)
O1—C7—C6	107.58 (12)	C18—C17—C16	133.19 (19)
O1—C7—H7A	110.2	O4—C17—C16	117.37 (14)
C6—C7—H7A	110.2	C17—C18—C19	106.5 (2)
O1—C7—H7B	110.2	C17—C18—H18	126.7
C6—C7—H7B	110.2	C19—C18—H18	126.7
H7A—C7—H7B	108.5	C20—C19—C18	106.89 (19)
O1—C8—C9	124.48 (14)	C20—C19—H19	126.6
O1—C8—C13	116.21 (13)	C18—C19—H19	126.6
C9—C8—C13	119.29 (14)	C19—C20—O4	111.2 (2)
C10—C9—C8	119.65 (15)	C19—C20—H20	124.4
C10—C9—H9	120.2	O4—C20—H20	124.4
C8—C9—H9	120.2	C8—O1—C7	118.05 (11)
C9—C10—C11	122.26 (15)	C14—O2—H2A	99.0 (11)
C9—C10—H10	118.9	C16—O3—H2A	95.5 (9)
C11—C10—H10	118.9	C20—O4—C17	105.94 (16)
C10—C11—C12	117.10 (14)
C6—C1—C2—C3	0.3 (3)	C12—C11—C14—O2	−178.85 (14)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C14—C15	−178.45 (15)
C2—C3—C4—C5	0.0 (3)	C12—C11—C14—C15	1.4 (2)
C3—C4—C5—C6	−0.1 (3)	O2—C14—C15—C16	−2.1 (2)
C2—C1—C6—C5	−0.4 (2)	C11—C14—C15—C16	177.71 (14)
C2—C1—C6—C7	179.38 (15)	C14—C15—C16—O3	2.4 (2)
C4—C5—C6—C1	0.4 (3)	C14—C15—C16—C17	−176.10 (14)
C4—C5—C6—C7	−179.47 (17)	O3—C16—C17—C18	−3.0 (3)
C1—C6—C7—O1	−111.01 (17)	C15—C16—C17—C18	175.63 (18)
C5—C6—C7—O1	68.82 (19)	O3—C16—C17—O4	178.65 (13)
O1—C8—C9—C10	179.06 (15)	C15—C16—C17—O4	−2.7 (2)
C13—C8—C9—C10	−2.5 (3)	O4—C17—C18—C19	0.0 (2)
C8—C9—C10—C11	0.2 (3)	C16—C17—C18—C19	−178.42 (17)
C9—C10—C11—C12	1.7 (3)	C17—C18—C19—C20	0.0 (2)
C9—C10—C11—C14	−178.47 (15)	C18—C19—C20—O4	0.0 (2)
C10—C11—C12—C13	−1.3 (2)	C9—C8—O1—C7	−8.7 (2)
C14—C11—C12—C13	178.88 (14)	C13—C8—O1—C7	172.83 (13)
C11—C12—C13—C8	−1.0 (2)	C6—C7—O1—C8	−171.88 (13)
O1—C8—C13—C12	−178.53 (13)	C19—C20—O4—C17	0.0 (2)
C9—C8—C13—C12	2.9 (2)	C18—C17—O4—C20	−0.02 (19)
C10—C11—C14—O2	1.3 (2)	C16—C17—O4—C20	178.72 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	1.15 (3)	1.38 (3)	2.5030 (16)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	1.15 (3)	1.38 (3)	2.5030 (16)	162 (2)