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

In the title compound, C(23)H(24)O(8)·H(2)O, the six-membered ring of the oxan-4-one (tetra-hydro-pyran-4-one) ring displays an envelope conformation with the heterocyclic O atom at the flap position. The dihedral angles between the terminal benzene rings is 37.23 (10)°. Classical intermolecular O-H⋯O and weak C-H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For pharmacological activity of curcumin [systematic name (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione], see: Maheshwari et al. (2006 ▶). The title compound is used in the preparation of curcumin analogues, see: Du et al. (2006a ▶,b ▶); Liu et al. (2008 ▶). For a related structure, see: Abaee et al. (2008 ▶). For the synthesis, see: Du et al. (2006a ▶,b ▶); Youssef et al. (2004 ▶).

Experimental

Crystal data

C23H24O8·H2O

M = 446.44

Monoclinic,

a = 9.203 (2) Å

b = 14.145 (3) Å

c = 17.011 (4) Å

β = 105.349 (5)°

V = 2135.5 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.43 × 0.40 × 0.32 mm

Data collection

Bruker SMART CCD 1000 area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.967

12756 measured reflections

4650 independent reflections

2502 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.116

S = 0.99

4650 reflections

295 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041930/xu5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041930/xu5053Isup2.hkl

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

C23H24O8·H2O	F(000) = 944
Mr = 446.44	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3096 reflections
a = 9.203 (2) Å	θ = 2.7–25.5°
b = 14.145 (3) Å	µ = 0.11 mm−1
c = 17.011 (4) Å	T = 293 K
β = 105.349 (5)°	Block, pale yellow
V = 2135.5 (9) Å3	0.43 × 0.40 × 0.32 mm
Z = 4

Bruker SMART CCD 1000 area-detector diffractometer	4650 independent reflections
Radiation source: fine-focus sealed tube	2502 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 27.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.955, Tmax = 0.967	k = −17→18
12756 measured reflections	l = −12→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3
4650 reflections	(Δ/σ)max < 0.001
295 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. The formulation was established by the NMR spectrum and ESI mass spectrum. 1H NMR (MSDO-d6, 300 MHz) δ (ppm): 9.03 (brs, 2H, -OH), 7.58 (s, 2H, -CH=), 6.70 (s, 4H, ArH), 4.95 (s, 4H, -CH2-O-CH2-), 3.81 (s, 12H, OCH3). The ESI mass spectrum showed ions at 412.

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	0.8908 (2)	0.32659 (13)	0.97171 (12)	0.0394 (5)
C2	0.8037 (2)	0.29050 (13)	1.02728 (12)	0.0394 (5)
C3	0.6896 (2)	0.35663 (14)	1.04616 (13)	0.0473 (6)
H3A	0.6147	0.3207	1.0643	0.057*
H3B	0.7390	0.3994	1.0896	0.057*
C4	0.7220 (2)	0.47300 (14)	0.95381 (15)	0.0498 (6)
H4A	0.7600	0.5166	0.9985	0.060*
H4B	0.6701	0.5096	0.9065	0.060*
C5	0.8524 (2)	0.42155 (13)	0.93530 (12)	0.0392 (5)
C6	0.8228 (2)	0.19984 (14)	1.05100 (13)	0.0455 (5)
H6	0.8920	0.1658	1.0311	0.055*
C7	0.7496 (2)	0.14758 (13)	1.10385 (13)	0.0417 (5)
C8	0.7119 (2)	0.05293 (13)	1.08579 (14)	0.0452 (5)
H8	0.7418	0.0233	1.0438	0.054*
C9	0.6305 (2)	0.00271 (13)	1.12948 (13)	0.0427 (5)
C10	0.5885 (2)	0.04587 (13)	1.19366 (13)	0.0403 (5)
C11	0.6329 (2)	0.13891 (14)	1.21437 (13)	0.0398 (5)
C12	0.7122 (2)	0.18956 (14)	1.16978 (13)	0.0428 (5)
H12	0.7406	0.2517	1.1839	0.051*
C13	0.9318 (2)	0.45266 (13)	0.88503 (13)	0.0410 (5)
H13	1.0080	0.4116	0.8805	0.049*
C14	0.9230 (2)	0.53765 (13)	0.83608 (13)	0.0395 (5)
C15	0.9862 (2)	0.53228 (13)	0.77028 (13)	0.0422 (5)
H15	1.0342	0.4771	0.7613	0.051*
C16	0.9781 (2)	0.60806 (13)	0.71856 (13)	0.0410 (5)
C17	0.9098 (2)	0.69190 (13)	0.73198 (13)	0.0401 (5)
C18	0.8509 (2)	0.69876 (13)	0.79906 (13)	0.0406 (5)
C19	0.8556 (2)	0.62257 (13)	0.85041 (13)	0.0408 (5)
H19	0.8140	0.6276	0.8945	0.049*
C20	0.6271 (3)	−0.13737 (15)	1.05107 (15)	0.0607 (7)
H20A	0.5826	−0.1071	0.9998	0.091*
H20B	0.5931	−0.2017	1.0490	0.091*
H20C	0.7349	−0.1362	1.0616	0.091*
C21	0.6141 (3)	0.26902 (15)	1.30040 (16)	0.0681 (7)
H21A	0.7204	0.2816	1.3147	0.102*
H21B	0.5747	0.2835	1.3459	0.102*
H21C	0.5646	0.3075	1.2547	0.102*
C22	1.1153 (3)	0.53010 (16)	0.63678 (16)	0.0637 (7)
H22A	1.2007	0.5215	0.6829	0.096*
H22B	1.1493	0.5405	0.5888	0.096*
H22C	1.0530	0.4746	0.6295	0.096*
C23	0.7318 (3)	0.79786 (15)	0.87680 (15)	0.0583 (6)
H23A	0.6518	0.7534	0.8741	0.088*
H23B	0.6936	0.8610	0.8768	0.088*
H23C	0.8104	0.7875	0.9259	0.088*
O1	0.99167 (17)	0.27831 (9)	0.95636 (9)	0.0512 (4)
O2	0.61814 (16)	0.40948 (10)	0.97496 (10)	0.0530 (4)
O3	0.58409 (18)	−0.08894 (9)	1.11397 (10)	0.0589 (4)
O4	0.50522 (17)	−0.00394 (9)	1.23443 (10)	0.0535 (4)
H4	0.4751	0.0316	1.2648	0.080*
O5	0.58841 (17)	0.17232 (9)	1.27958 (9)	0.0524 (4)
O6	1.03097 (17)	0.60926 (9)	0.65026 (10)	0.0564 (4)
O7	0.89910 (18)	0.76810 (9)	0.68224 (10)	0.0527 (4)
H7	0.9409	0.7564	0.6463	0.079*
O8	0.79014 (17)	0.78551 (9)	0.80853 (10)	0.0547 (4)
O1W	0.65172 (17)	0.92850 (11)	0.65729 (11)	0.0660 (5)
H1A	0.7002	0.8780	0.6759	0.099*
H1B	0.5849	0.9142	0.6119	0.099*

	U11	U22	U33	U12	U13	U23
C1	0.0492 (13)	0.0356 (11)	0.0326 (12)	−0.0025 (10)	0.0094 (11)	−0.0033 (9)
C2	0.0479 (12)	0.0356 (11)	0.0354 (13)	−0.0017 (9)	0.0120 (11)	−0.0005 (9)
C3	0.0536 (13)	0.0463 (12)	0.0442 (14)	0.0021 (10)	0.0167 (12)	0.0079 (11)
C4	0.0552 (14)	0.0403 (12)	0.0554 (15)	0.0015 (10)	0.0173 (12)	0.0078 (11)
C5	0.0464 (12)	0.0338 (11)	0.0369 (13)	−0.0033 (9)	0.0103 (11)	0.0004 (9)
C6	0.0536 (13)	0.0404 (12)	0.0456 (14)	−0.0003 (10)	0.0185 (12)	0.0013 (10)
C7	0.0470 (12)	0.0374 (11)	0.0423 (13)	0.0022 (10)	0.0149 (11)	0.0071 (10)
C8	0.0551 (13)	0.0378 (11)	0.0467 (14)	0.0045 (10)	0.0204 (12)	0.0045 (10)
C9	0.0487 (12)	0.0310 (11)	0.0483 (14)	0.0017 (9)	0.0129 (11)	0.0028 (10)
C10	0.0416 (11)	0.0368 (11)	0.0433 (13)	0.0022 (9)	0.0126 (11)	0.0078 (10)
C11	0.0445 (12)	0.0389 (11)	0.0364 (13)	0.0032 (9)	0.0111 (11)	0.0024 (10)
C12	0.0494 (12)	0.0343 (11)	0.0435 (14)	−0.0008 (9)	0.0102 (11)	0.0038 (10)
C13	0.0500 (12)	0.0321 (10)	0.0410 (13)	−0.0001 (9)	0.0121 (11)	0.0013 (10)
C14	0.0433 (11)	0.0321 (10)	0.0429 (13)	−0.0024 (9)	0.0112 (11)	0.0011 (9)
C15	0.0461 (12)	0.0323 (11)	0.0497 (14)	−0.0002 (9)	0.0155 (11)	0.0020 (10)
C16	0.0436 (12)	0.0383 (11)	0.0453 (14)	−0.0017 (9)	0.0190 (11)	0.0019 (10)
C17	0.0437 (12)	0.0323 (11)	0.0451 (14)	−0.0015 (9)	0.0133 (11)	0.0064 (10)
C18	0.0448 (12)	0.0292 (11)	0.0488 (14)	0.0020 (9)	0.0140 (11)	0.0007 (10)
C19	0.0475 (12)	0.0362 (11)	0.0415 (13)	−0.0030 (9)	0.0167 (11)	0.0008 (10)
C20	0.0782 (17)	0.0438 (13)	0.0601 (17)	0.0027 (12)	0.0184 (14)	−0.0078 (12)
C21	0.094 (2)	0.0520 (15)	0.0655 (18)	−0.0044 (13)	0.0329 (16)	−0.0146 (13)
C22	0.0762 (17)	0.0526 (14)	0.0759 (19)	0.0133 (12)	0.0440 (16)	0.0072 (13)
C23	0.0667 (15)	0.0494 (13)	0.0644 (17)	0.0141 (11)	0.0269 (14)	0.0014 (12)
O1	0.0681 (10)	0.0414 (8)	0.0521 (10)	0.0110 (7)	0.0299 (9)	0.0080 (7)
O2	0.0484 (9)	0.0532 (9)	0.0581 (10)	0.0032 (7)	0.0155 (8)	0.0173 (8)
O3	0.0842 (11)	0.0372 (8)	0.0632 (11)	−0.0119 (8)	0.0334 (10)	−0.0059 (8)
O4	0.0651 (10)	0.0424 (8)	0.0620 (12)	−0.0067 (7)	0.0328 (9)	0.0020 (8)
O5	0.0698 (10)	0.0421 (8)	0.0523 (10)	−0.0040 (7)	0.0285 (9)	−0.0043 (7)
O6	0.0751 (11)	0.0425 (8)	0.0638 (11)	0.0120 (7)	0.0399 (10)	0.0117 (8)
O7	0.0715 (11)	0.0363 (8)	0.0578 (11)	0.0075 (7)	0.0303 (9)	0.0122 (8)
O8	0.0743 (11)	0.0387 (8)	0.0598 (11)	0.0117 (7)	0.0328 (9)	0.0061 (7)
O1W	0.0629 (10)	0.0578 (10)	0.0766 (13)	−0.0020 (8)	0.0171 (9)	0.0005 (9)

C1—O1	1.234 (2)	C15—C16	1.376 (3)
C1—C5	1.482 (3)	C15—H15	0.9300
C1—C2	1.483 (3)	C16—O6	1.374 (2)
C2—C6	1.342 (3)	C16—C17	1.389 (3)
C2—C3	1.503 (3)	C17—O7	1.358 (2)
C3—O2	1.427 (2)	C17—C18	1.390 (3)
C3—H3A	0.9700	C18—O8	1.376 (2)
C3—H3B	0.9700	C18—C19	1.381 (3)
C4—O2	1.426 (2)	C19—H19	0.9300
C4—C5	1.506 (3)	C20—O3	1.413 (3)
C4—H4A	0.9700	C20—H20A	0.9600
C4—H4B	0.9700	C20—H20B	0.9600
C5—C13	1.338 (3)	C20—H20C	0.9600
C6—C7	1.460 (3)	C21—O5	1.417 (2)
C6—H6	0.9300	C21—H21A	0.9600
C7—C12	1.390 (3)	C21—H21B	0.9600
C7—C8	1.397 (3)	C21—H21C	0.9600
C8—C9	1.383 (3)	C22—O6	1.415 (2)
C8—H8	0.9300	C22—H22A	0.9600
C9—O3	1.369 (2)	C22—H22B	0.9600
C9—C10	1.392 (3)	C22—H22C	0.9600
C10—O4	1.358 (2)	C23—O8	1.413 (3)
C10—C11	1.395 (3)	C23—H23A	0.9600
C11—O5	1.365 (2)	C23—H23B	0.9600
C11—C12	1.384 (3)	C23—H23C	0.9600
C12—H12	0.9300	O4—H4	0.8200
C13—C14	1.452 (3)	O7—H7	0.8200
C13—H13	0.9300	O1W—H1A	0.8572
C14—C15	1.393 (3)	O1W—H1B	0.8743
C14—C19	1.403 (3)
O1—C1—C5	121.49 (18)	C16—C15—C14	120.50 (18)
O1—C1—C2	120.54 (17)	C16—C15—H15	119.8
C5—C1—C2	117.97 (18)	C14—C15—H15	119.8
C6—C2—C1	118.06 (18)	O6—C16—C15	125.38 (18)
C6—C2—C3	125.04 (19)	O6—C16—C17	113.92 (17)
C1—C2—C3	116.64 (17)	C15—C16—C17	120.70 (19)
O2—C3—C2	109.61 (17)	O7—C17—C16	122.48 (19)
O2—C3—H3A	109.7	O7—C17—C18	118.44 (17)
C2—C3—H3A	109.7	C16—C17—C18	119.08 (18)
O2—C3—H3B	109.7	O8—C18—C19	124.58 (19)
C2—C3—H3B	109.7	O8—C18—C17	114.67 (17)
H3A—C3—H3B	108.2	C19—C18—C17	120.75 (18)
O2—C4—C5	111.89 (16)	C18—C19—C14	119.97 (19)
O2—C4—H4A	109.2	C18—C19—H19	120.0
C5—C4—H4A	109.2	C14—C19—H19	120.0
O2—C4—H4B	109.2	O3—C20—H20A	109.5
C5—C4—H4B	109.2	O3—C20—H20B	109.5
H4A—C4—H4B	107.9	H20A—C20—H20B	109.5
C13—C5—C1	117.08 (18)	O3—C20—H20C	109.5
C13—C5—C4	125.08 (18)	H20A—C20—H20C	109.5
C1—C5—C4	117.74 (17)	H20B—C20—H20C	109.5
C2—C6—C7	128.60 (19)	O5—C21—H21A	109.5
C2—C6—H6	115.7	O5—C21—H21B	109.5
C7—C6—H6	115.7	H21A—C21—H21B	109.5
C12—C7—C8	119.13 (19)	O5—C21—H21C	109.5
C12—C7—C6	122.26 (18)	H21A—C21—H21C	109.5
C8—C7—C6	118.58 (19)	H21B—C21—H21C	109.5
C9—C8—C7	120.8 (2)	O6—C22—H22A	109.5
C9—C8—H8	119.6	O6—C22—H22B	109.5
C7—C8—H8	119.6	H22A—C22—H22B	109.5
O3—C9—C8	124.67 (19)	O6—C22—H22C	109.5
O3—C9—C10	115.41 (18)	H22A—C22—H22C	109.5
C8—C9—C10	119.92 (18)	H22B—C22—H22C	109.5
O4—C10—C9	118.97 (18)	O8—C23—H23A	109.5
O4—C10—C11	121.84 (19)	O8—C23—H23B	109.5
C9—C10—C11	119.19 (19)	H23A—C23—H23B	109.5
O5—C11—C12	125.57 (18)	O8—C23—H23C	109.5
O5—C11—C10	113.63 (17)	H23A—C23—H23C	109.5
C12—C11—C10	120.8 (2)	H23B—C23—H23C	109.5
C11—C12—C7	120.00 (19)	C4—O2—C3	110.80 (16)
C11—C12—H12	120.0	C9—O3—C20	118.01 (17)
C7—C12—H12	120.0	C10—O4—H4	109.5
C5—C13—C14	132.99 (19)	C11—O5—C21	118.12 (17)
C5—C13—H13	113.5	C16—O6—C22	117.36 (16)
C14—C13—H13	113.5	C17—O7—H7	109.5
C15—C14—C19	118.95 (18)	C18—O8—C23	117.46 (16)
C15—C14—C13	116.33 (18)	H1A—O1W—H1B	108.0
C19—C14—C13	124.71 (19)
O1—C1—C2—C6	−9.1 (3)	C6—C7—C12—C11	175.20 (19)
C5—C1—C2—C6	170.58 (19)	C1—C5—C13—C14	176.8 (2)
O1—C1—C2—C3	176.48 (19)	C4—C5—C13—C14	0.4 (4)
C5—C1—C2—C3	−3.8 (3)	C5—C13—C14—C15	−158.0 (2)
C6—C2—C3—O2	−136.3 (2)	C5—C13—C14—C19	21.6 (4)
C1—C2—C3—O2	37.7 (2)	C19—C14—C15—C16	−2.2 (3)
O1—C1—C5—C13	0.0 (3)	C13—C14—C15—C16	177.47 (18)
C2—C1—C5—C13	−179.67 (18)	C14—C15—C16—O6	−177.28 (19)
O1—C1—C5—C4	176.63 (19)	C14—C15—C16—C17	1.5 (3)
C2—C1—C5—C4	−3.1 (3)	O6—C16—C17—O7	−0.9 (3)
O2—C4—C5—C13	152.0 (2)	C15—C16—C17—O7	−179.78 (19)
O2—C4—C5—C1	−24.3 (3)	O6—C16—C17—C18	179.54 (18)
C1—C2—C6—C7	−179.0 (2)	C15—C16—C17—C18	0.7 (3)
C3—C2—C6—C7	−5.1 (4)	O7—C17—C18—O8	−1.6 (3)
C2—C6—C7—C12	−35.3 (3)	C16—C17—C18—O8	178.00 (18)
C2—C6—C7—C8	142.7 (2)	O7—C17—C18—C19	178.38 (19)
C12—C7—C8—C9	3.9 (3)	C16—C17—C18—C19	−2.0 (3)
C6—C7—C8—C9	−174.22 (19)	O8—C18—C19—C14	−178.75 (18)
C7—C8—C9—O3	177.48 (19)	C17—C18—C19—C14	1.3 (3)
C7—C8—C9—C10	−1.6 (3)	C15—C14—C19—C18	0.8 (3)
O3—C9—C10—O4	−0.8 (3)	C13—C14—C19—C18	−178.80 (19)
C8—C9—C10—O4	178.29 (19)	C5—C4—O2—C3	60.9 (2)
O3—C9—C10—C11	179.12 (18)	C2—C3—O2—C4	−67.7 (2)
C8—C9—C10—C11	−1.7 (3)	C8—C9—O3—C20	2.7 (3)
O4—C10—C11—O5	1.7 (3)	C10—C9—O3—C20	−178.19 (19)
C9—C10—C11—O5	−178.28 (18)	C12—C11—O5—C21	5.3 (3)
O4—C10—C11—C12	−177.24 (19)	C10—C11—O5—C21	−173.58 (19)
C9—C10—C11—C12	2.8 (3)	C15—C16—O6—C22	−7.4 (3)
O5—C11—C12—C7	−179.31 (18)	C17—C16—O6—C22	173.82 (19)
C10—C11—C12—C7	−0.5 (3)	C19—C18—O8—C23	1.6 (3)
C8—C7—C12—C11	−2.8 (3)	C17—C18—O8—C23	−178.42 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1Wi	0.82	2.06	2.833 (2)	156
O7—H7···O1ii	0.82	2.03	2.801 (2)	157
O1W—H1A···O7	0.86	2.38	3.162 (2)	152
O1W—H1B···O2iii	0.87	2.05	2.888 (2)	160
C13—H13···O7iv	0.93	2.54	3.390 (3)	151
C23—H23C···O1v	0.96	2.50	3.445 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1Wi	0.82	2.06	2.833 (2)	156
O7—H7⋯O1ii	0.82	2.03	2.801 (2)	157
O1W—H1A⋯O7	0.86	2.38	3.162 (2)	152
O1W—H1B⋯O2iii	0.87	2.05	2.888 (2)	160
C13—H13⋯O7iv	0.93	2.54	3.390 (3)	151
C23—H23C⋯O1v	0.96	2.50	3.445 (3)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .