(3E,5E)-3,5-Bis(4-hy-droxy-benzyl-idene)oxan-4-one.

In the title compound, C(19)H(16)O(4), there are two 4-hy-droxy-benzyl substituents on the oxan-4-one (tetra-hydro-pyran-4-one) ring, which exhibits an envelope conformation. The dihedral angles between pyran-one ring and the two benzene rings are 26.69 (9) and 36.01 (9)° while the benzene rings make a dihedral angle of 20.88 (10)°. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds into a supra-molecular three-dimensional twofold inter-penetrating hydrogen-bonded network.

Related literature

For the pharmacological activity or curcumin [systematic name (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-hep­ta­diene-3,5-dione], see: Maheshwari et al. (2006 ▶). For curcumin analogues, see: Liang et al. (2009 ▶). For the synthesis of the title compound, see: Youssef et al. (2004 ▶); Du et al. (2006 ▶). For related structures, see: Abaee et al. (2008 ▶); Du et al. (2006 ▶).

Experimental

Crystal data

C19H16O4

M = 308.32

Orthorhombic,

a = 11.812 (3) Å

b = 7.4687 (16) Å

c = 33.233 (7) Å

V = 2931.9 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.42 × 0.37 × 0.29 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.972

16659 measured reflections

3224 independent reflections

1941 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.04

3224 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; 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/S1600536810051457/jh2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051457/jh2219Isup2.hkl

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

C19H16O4	F(000) = 1296
Mr = 308.32	Dx = 1.397 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3683 reflections
a = 11.812 (3) Å	θ = 2.5–26.7°
b = 7.4687 (16) Å	µ = 0.10 mm−1
c = 33.233 (7) Å	T = 293 K
V = 2931.9 (11) Å3	Block, colourless
Z = 8	0.42 × 0.37 × 0.29 mm

Bruker SMART CCD 1K area-detector diffractometer	3224 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 27.1°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.960, Tmax = 0.972	k = −8→9
16659 measured reflections	l = −42→40

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.5774P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3224 reflections	Δρmax = 0.17 e Å−3
211 parameters	Δρmin = −0.18 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: 0.0029 (5)

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
C1	0.91919 (16)	0.7445 (3)	0.61879 (5)	0.0348 (4)
C2	0.88020 (14)	0.8252 (2)	0.58058 (5)	0.0322 (4)
C3	0.79877 (16)	0.9793 (3)	0.58346 (5)	0.0374 (5)
H3A	0.8083	1.0564	0.5602	0.045*
H3B	0.7219	0.9337	0.5831	0.045*
C4	0.79701 (16)	0.9771 (3)	0.65410 (5)	0.0374 (5)
H4A	0.7206	0.9298	0.6536	0.045*
H4B	0.8042	1.0530	0.6776	0.045*
C5	0.87964 (15)	0.8251 (2)	0.65713 (5)	0.0323 (4)
C6	0.92068 (15)	0.7571 (3)	0.54608 (5)	0.0342 (4)
H6	0.9721	0.6642	0.5496	0.041*
C7	0.89904 (14)	0.8015 (2)	0.50413 (5)	0.0327 (4)
C8	0.97612 (15)	0.7402 (3)	0.47550 (6)	0.0386 (5)
H8	1.0364	0.6693	0.4839	0.046*
C9	0.96621 (15)	0.7811 (3)	0.43528 (6)	0.0404 (5)
H9	1.0188	0.7372	0.4169	0.048*
C10	0.87774 (16)	0.8876 (3)	0.42219 (6)	0.0395 (5)
C11	0.79695 (16)	0.9439 (3)	0.44952 (6)	0.0440 (5)
H11	0.7354	1.0111	0.4408	0.053*
C12	0.80732 (16)	0.9009 (3)	0.48974 (6)	0.0410 (5)
H12	0.7519	0.9389	0.5077	0.049*
C13	0.91900 (14)	0.7598 (3)	0.69197 (5)	0.0340 (4)
H13	0.9732	0.6703	0.6894	0.041*
C14	0.89027 (15)	0.8069 (2)	0.73343 (5)	0.0322 (4)
C15	0.96953 (15)	0.7720 (3)	0.76362 (5)	0.0366 (5)
H15	1.0367	0.7144	0.7569	0.044*
C16	0.95080 (15)	0.8209 (3)	0.80322 (6)	0.0387 (5)
H16	1.0048	0.7966	0.8228	0.046*
C17	0.85055 (15)	0.9063 (3)	0.81330 (6)	0.0381 (5)
C18	0.76801 (16)	0.9319 (3)	0.78463 (6)	0.0401 (5)
H18	0.6989	0.9821	0.7919	0.048*
C19	0.78746 (15)	0.8832 (2)	0.74526 (6)	0.0373 (5)
H19	0.7311	0.9014	0.7262	0.045*
O1	0.98058 (13)	0.6110 (2)	0.61862 (4)	0.0528 (4)
O2	0.81578 (11)	1.08088 (17)	0.61899 (4)	0.0395 (3)
O3	0.87617 (13)	0.9311 (2)	0.38255 (4)	0.0589 (4)
H3	0.8139	0.9718	0.3766	0.088*
O4	0.83014 (11)	0.9651 (2)	0.85156 (4)	0.0542 (4)
H4	0.8896	0.9992	0.8618	0.081*

	U11	U22	U33	U12	U13	U23
C1	0.0388 (10)	0.0336 (10)	0.0321 (10)	0.0021 (8)	−0.0001 (8)	−0.0024 (9)
C2	0.0376 (10)	0.0295 (10)	0.0294 (10)	−0.0016 (8)	0.0009 (8)	0.0011 (8)
C3	0.0434 (11)	0.0372 (11)	0.0316 (11)	0.0040 (8)	0.0004 (9)	0.0003 (9)
C4	0.0475 (11)	0.0368 (11)	0.0279 (10)	0.0060 (8)	0.0027 (8)	0.0010 (8)
C5	0.0360 (10)	0.0315 (10)	0.0295 (10)	−0.0003 (8)	−0.0007 (8)	−0.0016 (8)
C6	0.0369 (10)	0.0320 (10)	0.0338 (11)	0.0030 (8)	−0.0009 (8)	0.0013 (9)
C7	0.0375 (10)	0.0308 (10)	0.0299 (10)	−0.0007 (8)	0.0011 (8)	−0.0006 (8)
C8	0.0386 (11)	0.0413 (11)	0.0361 (11)	0.0057 (9)	−0.0003 (8)	−0.0013 (9)
C9	0.0412 (11)	0.0471 (12)	0.0328 (11)	0.0019 (9)	0.0066 (9)	−0.0055 (9)
C10	0.0441 (11)	0.0427 (12)	0.0317 (11)	−0.0042 (9)	−0.0012 (9)	0.0017 (9)
C11	0.0453 (12)	0.0467 (12)	0.0401 (12)	0.0122 (9)	−0.0050 (9)	0.0005 (10)
C12	0.0394 (11)	0.0494 (12)	0.0342 (11)	0.0065 (9)	0.0028 (8)	−0.0030 (9)
C13	0.0372 (10)	0.0321 (10)	0.0329 (11)	0.0014 (8)	−0.0011 (8)	−0.0041 (9)
C14	0.0378 (10)	0.0294 (10)	0.0295 (10)	−0.0004 (8)	−0.0018 (8)	−0.0016 (8)
C15	0.0356 (10)	0.0385 (11)	0.0359 (11)	0.0026 (8)	0.0006 (8)	−0.0028 (9)
C16	0.0382 (11)	0.0472 (12)	0.0307 (11)	−0.0009 (9)	−0.0059 (8)	−0.0019 (9)
C17	0.0436 (11)	0.0402 (11)	0.0306 (11)	−0.0048 (9)	0.0028 (9)	−0.0077 (9)
C18	0.0372 (11)	0.0451 (12)	0.0379 (11)	0.0022 (9)	0.0036 (9)	−0.0029 (10)
C19	0.0370 (11)	0.0412 (11)	0.0336 (11)	0.0002 (8)	−0.0038 (8)	0.0017 (9)
O1	0.0708 (10)	0.0518 (9)	0.0357 (8)	0.0293 (8)	−0.0031 (7)	−0.0019 (7)
O2	0.0563 (9)	0.0305 (7)	0.0316 (7)	0.0050 (6)	0.0022 (6)	0.0008 (6)
O3	0.0632 (10)	0.0830 (12)	0.0305 (8)	0.0091 (9)	−0.0008 (7)	0.0092 (8)
O4	0.0501 (9)	0.0778 (11)	0.0346 (8)	−0.0016 (8)	0.0036 (7)	−0.0213 (8)

C1—O1	1.233 (2)	C10—O3	1.357 (2)
C1—C2	1.479 (2)	C10—C11	1.383 (3)
C1—C5	1.485 (2)	C11—C12	1.380 (3)
C2—C6	1.343 (2)	C11—H11	0.9300
C2—C3	1.503 (2)	C12—H12	0.9300
C3—O2	1.418 (2)	C13—C14	1.462 (2)
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.397 (2)
C4—O2	1.418 (2)	C14—C19	1.398 (2)
C4—C5	1.501 (3)	C15—C16	1.383 (2)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.386 (3)
C5—C13	1.340 (2)	C16—H16	0.9300
C6—C7	1.455 (2)	C17—O4	1.367 (2)
C6—H6	0.9300	C17—C18	1.376 (3)
C7—C8	1.394 (2)	C18—C19	1.377 (2)
C7—C12	1.398 (2)	C18—H18	0.9300
C8—C9	1.376 (3)	C19—H19	0.9300
C8—H8	0.9300	O3—H3	0.8200
C9—C10	1.383 (3)	O4—H4	0.8200
C9—H9	0.9300
O1—C1—C2	120.58 (16)	O3—C10—C11	123.72 (18)
O1—C1—C5	121.12 (17)	O3—C10—C9	116.96 (17)
C2—C1—C5	118.27 (16)	C11—C10—C9	119.32 (18)
C6—C2—C1	117.91 (17)	C12—C11—C10	120.24 (18)
C6—C2—C3	124.92 (16)	C12—C11—H11	119.9
C1—C2—C3	117.18 (15)	C10—C11—H11	119.9
O2—C3—C2	111.83 (14)	C11—C12—C7	121.60 (18)
O2—C3—H3A	109.2	C11—C12—H12	119.2
C2—C3—H3A	109.2	C7—C12—H12	119.2
O2—C3—H3B	109.2	C5—C13—C14	130.28 (18)
C2—C3—H3B	109.2	C5—C13—H13	114.9
H3A—C3—H3B	107.9	C14—C13—H13	114.9
O2—C4—C5	111.52 (14)	C15—C14—C19	117.14 (16)
O2—C4—H4A	109.3	C15—C14—C13	118.46 (16)
C5—C4—H4A	109.3	C19—C14—C13	124.39 (16)
O2—C4—H4B	109.3	C16—C15—C14	121.80 (17)
C5—C4—H4B	109.3	C16—C15—H15	119.1
H4A—C4—H4B	108.0	C14—C15—H15	119.1
C13—C5—C1	119.01 (17)	C15—C16—C17	119.20 (17)
C13—C5—C4	123.99 (16)	C15—C16—H16	120.4
C1—C5—C4	116.99 (15)	C17—C16—H16	120.4
C2—C6—C7	132.00 (17)	O4—C17—C18	118.33 (17)
C2—C6—H6	114.0	O4—C17—C16	121.56 (17)
C7—C6—H6	114.0	C18—C17—C16	120.10 (18)
C8—C7—C12	116.55 (17)	C17—C18—C19	120.19 (18)
C8—C7—C6	117.65 (16)	C17—C18—H18	119.9
C12—C7—C6	125.80 (16)	C19—C18—H18	119.9
C9—C8—C7	122.31 (18)	C18—C19—C14	121.31 (17)
C9—C8—H8	118.8	C18—C19—H19	119.3
C7—C8—H8	118.8	C14—C19—H19	119.3
C8—C9—C10	119.82 (17)	C3—O2—C4	111.76 (14)
C8—C9—H9	120.1	C10—O3—H3	109.5
C10—C9—H9	120.1	C17—O4—H4	109.5
O1—C1—C2—C6	−5.0 (3)	O3—C10—C11—C12	−176.96 (19)
C5—C1—C2—C6	176.83 (17)	C9—C10—C11—C12	2.8 (3)
O1—C1—C2—C3	175.61 (18)	C10—C11—C12—C7	0.6 (3)
C5—C1—C2—C3	−2.6 (2)	C8—C7—C12—C11	−3.3 (3)
C6—C2—C3—O2	−148.76 (18)	C6—C7—C12—C11	176.68 (19)
C1—C2—C3—O2	30.6 (2)	C1—C5—C13—C14	−176.43 (17)
O1—C1—C5—C13	5.4 (3)	C4—C5—C13—C14	3.7 (3)
C2—C1—C5—C13	−176.41 (16)	C5—C13—C14—C15	−156.10 (19)
O1—C1—C5—C4	−174.69 (18)	C5—C13—C14—C19	24.7 (3)
C2—C1—C5—C4	3.5 (2)	C19—C14—C15—C16	−4.0 (3)
O2—C4—C5—C13	147.53 (18)	C13—C14—C15—C16	176.72 (18)
O2—C4—C5—C1	−32.3 (2)	C14—C15—C16—C17	0.2 (3)
C1—C2—C6—C7	178.79 (18)	C15—C16—C17—O4	−176.80 (18)
C3—C2—C6—C7	−1.9 (3)	C15—C16—C17—C18	4.0 (3)
C2—C6—C7—C8	162.9 (2)	O4—C17—C18—C19	176.59 (18)
C2—C6—C7—C12	−17.0 (3)	C16—C17—C18—C19	−4.2 (3)
C12—C7—C8—C9	2.8 (3)	C17—C18—C19—C14	0.2 (3)
C6—C7—C8—C9	−177.20 (17)	C15—C14—C19—C18	3.9 (3)
C7—C8—C9—C10	0.5 (3)	C13—C14—C19—C18	−176.94 (18)
C8—C9—C10—O3	176.46 (18)	C2—C3—O2—C4	−62.06 (19)
C8—C9—C10—C11	−3.4 (3)	C5—C4—O2—C3	62.96 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4i	0.82	1.95	2.757 (2)	167
O4—H4···O1ii	0.82	1.86	2.677 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.82	1.95	2.757 (2)	167
O4—H4⋯O1ii	0.82	1.86	2.677 (2)	171

Symmetry codes: (i) ; (ii) .