(2E,5E)-2,5-Bis(4-hy-droxy-3-meth-oxy-benzyl-idene)cyclo-penta-none ethanol monosolvate.

In the title structure, C21H20O5·C2H5OH, the curcumine-type mol-ecule has a double E conformation for the two benzyl-idene double bonds [C=C = 1.342 (4) and 1.349 (4) Å] and is nearly planar with respect to the non-H atoms (r.m.s. deviation from planarity = 0.069 Å). The two phenolic OH groups form bifurcated hydrogen bonds with intra-molecular branches to adjacent meth-oxy O atoms and inter-molecular branches to either a neighbouring mol-ecule or an ethanol solvent mol-ecule. The ethanol O atom donates a hydrogen bond to the keto O atom. These hydrogen bonds link the constituents into layers parallel to (101) in the crystal structure.

Related literature

For the biological activity of curcumin-type compounds, see: Ohori et al. (2006 ▶); Da’i et al. (2007 ▶); Anand et al. (2008 ▶). For the synthesis of the title compound, see: Sardjiman et al. (1997 ▶). For related structures, see: Du et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C21H20O5·C2H6O

M = 398.45

Monoclinic,

a = 8.880 (4) Å

b = 17.050 (5) Å

c = 13.950 (5) Å

β = 103.527 (14)°

V = 2053.4 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.12 × 0.10 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.671, T max = 0.994

16083 measured reflections

3720 independent reflections

1748 reflections with I > 2σ(I)

R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.157

S = 1.00

3720 reflections

268 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005229/qk2050sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005229/qk2050Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005229/qk2050Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005229/qk2050Isup4.cml

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

C21H20O5·C2H6O	F(000) = 848.00
Mr = 398.45	Dx = 1.289 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 7488 reflections
a = 8.880 (4) Å	θ = 3.0–25.3°
b = 17.050 (5) Å	µ = 0.09 mm−1
c = 13.950 (5) Å	T = 296 K
β = 103.527 (14)°	Block, yellow
V = 2053.4 (13) Å3	0.12 × 0.10 × 0.06 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3720 independent reflections
Radiation source: fine-focus sealed tube	1748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.119
ω scans	θmax = 25.4°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −10→10
Tmin = 0.671, Tmax = 0.994	k = −19→20
16083 measured reflections	l = −16→13

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4936P] where P = (Fo2 + 2Fc2)/3
3720 reflections	(Δ/σ)max < 0.001
268 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	0.8369 (3)	0.06512 (12)	0.4353 (2)	0.0667 (8)
O2	0.5966 (3)	−0.31177 (12)	0.67112 (19)	0.0615 (8)
O3	0.7414 (4)	−0.40870 (12)	0.5739 (2)	0.0710 (8)
H12	0.6808	−0.4176	0.6088	0.107*
O4	0.4611 (3)	0.35840 (12)	0.73021 (19)	0.0604 (8)
O5	0.5611 (3)	0.48579 (11)	0.65321 (19)	0.0633 (8)
H20	0.5129	0.4816	0.6964	0.095*
C1	0.7723 (4)	0.05470 (17)	0.5029 (3)	0.0476 (9)
C2	0.7402 (4)	−0.02157 (17)	0.5437 (2)	0.0445 (9)
C3	0.6494 (4)	−0.00895 (16)	0.6200 (3)	0.0486 (9)
H1	0.7029	−0.0318	0.6824	0.058*
H2	0.5480	−0.0330	0.5996	0.058*
C4	0.6338 (4)	0.08115 (17)	0.6307 (3)	0.0503 (10)
H3	0.5256	0.0963	0.6174	0.060*
H4	0.6845	0.0980	0.6967	0.060*
C5	0.7110 (4)	0.11694 (17)	0.5560 (2)	0.0437 (9)
C6	0.7921 (4)	−0.08723 (17)	0.5092 (3)	0.0479 (9)
H5	0.8498	−0.0782	0.4626	0.057*
C7	0.7754 (4)	−0.16971 (17)	0.5307 (2)	0.0444 (9)
C8	0.6881 (4)	−0.19778 (17)	0.5944 (2)	0.0459 (9)
H6	0.6365	−0.1626	0.6265	0.055*
C9	0.6773 (4)	−0.27714 (18)	0.6102 (3)	0.0467 (9)
C10	0.7508 (4)	−0.33004 (18)	0.5607 (3)	0.0501 (10)
C11	0.8375 (5)	−0.30373 (18)	0.4982 (3)	0.0548 (10)
H7	0.8880	−0.3392	0.4660	0.066*
C12	0.8498 (4)	−0.22375 (17)	0.4831 (3)	0.0521 (10)
H8	0.9088	−0.2060	0.4404	0.062*
C13	0.5081 (5)	−0.2631 (2)	0.7187 (3)	0.0695 (12)
H9	0.4335	−0.2347	0.6703	0.104*
H10	0.5753	−0.2268	0.7609	0.104*
H11	0.4554	−0.2948	0.7575	0.104*
C14	0.7297 (4)	0.19233 (17)	0.5318 (2)	0.0469 (9)
H13	0.7838	0.1983	0.4826	0.056*
C15	0.6821 (4)	0.26566 (16)	0.5675 (2)	0.0429 (9)
C16	0.5905 (4)	0.27266 (17)	0.6358 (2)	0.0441 (9)
H14	0.5571	0.2276	0.6622	0.053*
C17	0.5488 (4)	0.34504 (18)	0.6647 (2)	0.0463 (9)
C18	0.5994 (4)	0.41270 (18)	0.6257 (3)	0.0489 (9)
C19	0.6884 (5)	0.40735 (19)	0.5584 (3)	0.0588 (11)
H15	0.7217	0.4526	0.5323	0.071*
C20	0.7290 (4)	0.33428 (18)	0.5292 (3)	0.0541 (10)
H16	0.7891	0.3310	0.4829	0.065*
C21	0.3987 (4)	0.29279 (19)	0.7699 (3)	0.0586 (11)
H17	0.4815	0.2599	0.8044	0.088*
H18	0.3334	0.2636	0.7175	0.088*
H19	0.3389	0.3105	0.8149	0.088*
O6	0.1141 (4)	0.02592 (15)	0.7218 (2)	0.0752 (9)
H26	0.1194	−0.0016	0.6746	0.113*
C22	0.3617 (9)	−0.0071 (4)	0.8151 (6)	0.172 (3)
H21	0.4563	0.0143	0.8541	0.257*
H22	0.3847	−0.0413	0.7657	0.257*
H23	0.3098	−0.0362	0.8568	0.257*
C23	0.2672 (9)	0.0531 (3)	0.7700 (5)	0.122 (2)
H24	0.3141	0.0781	0.7217	0.147*
H25	0.2586	0.0921	0.8191	0.147*

	U11	U22	U33	U12	U13	U23
O1	0.094 (2)	0.0421 (14)	0.080 (2)	−0.0005 (13)	0.0528 (19)	−0.0005 (12)
O2	0.069 (2)	0.0486 (14)	0.0746 (19)	0.0009 (13)	0.0332 (16)	0.0090 (12)
O3	0.092 (2)	0.0348 (14)	0.097 (2)	−0.0040 (13)	0.0435 (17)	0.0012 (12)
O4	0.079 (2)	0.0435 (14)	0.0726 (19)	−0.0005 (12)	0.0454 (17)	0.0038 (12)
O5	0.090 (2)	0.0348 (13)	0.078 (2)	0.0002 (12)	0.0455 (17)	−0.0016 (11)
C1	0.052 (3)	0.037 (2)	0.057 (3)	−0.0001 (16)	0.019 (2)	−0.0001 (17)
C2	0.043 (2)	0.040 (2)	0.051 (2)	−0.0009 (15)	0.013 (2)	−0.0001 (16)
C3	0.056 (3)	0.0378 (18)	0.053 (2)	−0.0033 (16)	0.015 (2)	0.0043 (15)
C4	0.061 (3)	0.0409 (19)	0.054 (2)	−0.0044 (17)	0.022 (2)	−0.0033 (16)
C5	0.046 (2)	0.0357 (19)	0.051 (2)	−0.0039 (15)	0.0140 (19)	0.0004 (15)
C6	0.053 (3)	0.043 (2)	0.052 (2)	0.0002 (17)	0.020 (2)	0.0017 (16)
C7	0.049 (3)	0.0351 (19)	0.050 (2)	0.0004 (16)	0.012 (2)	0.0022 (15)
C8	0.049 (3)	0.040 (2)	0.051 (2)	0.0038 (16)	0.015 (2)	0.0010 (16)
C9	0.049 (3)	0.041 (2)	0.053 (2)	−0.0049 (16)	0.017 (2)	0.0039 (16)
C10	0.055 (3)	0.036 (2)	0.059 (3)	−0.0047 (17)	0.014 (2)	0.0006 (17)
C11	0.063 (3)	0.039 (2)	0.067 (3)	0.0010 (17)	0.026 (2)	−0.0100 (17)
C12	0.061 (3)	0.039 (2)	0.060 (3)	0.0009 (17)	0.023 (2)	−0.0033 (16)
C13	0.070 (3)	0.078 (3)	0.070 (3)	0.007 (2)	0.034 (3)	0.006 (2)
C14	0.054 (3)	0.046 (2)	0.044 (2)	−0.0016 (17)	0.018 (2)	−0.0015 (16)
C15	0.051 (3)	0.0325 (18)	0.048 (2)	−0.0010 (15)	0.016 (2)	0.0000 (15)
C16	0.052 (3)	0.0359 (19)	0.048 (2)	−0.0040 (16)	0.018 (2)	0.0014 (15)
C17	0.050 (3)	0.042 (2)	0.049 (2)	−0.0051 (16)	0.018 (2)	−0.0027 (16)
C18	0.059 (3)	0.037 (2)	0.054 (2)	−0.0043 (17)	0.020 (2)	−0.0039 (16)
C19	0.079 (3)	0.038 (2)	0.071 (3)	−0.0042 (19)	0.042 (3)	0.0082 (18)
C20	0.072 (3)	0.041 (2)	0.060 (3)	−0.0007 (18)	0.037 (2)	0.0005 (17)
C21	0.068 (3)	0.058 (2)	0.058 (3)	−0.0111 (19)	0.033 (2)	−0.0002 (18)
O6	0.092 (3)	0.0635 (18)	0.082 (2)	−0.0124 (16)	0.0453 (19)	−0.0068 (14)
C22	0.151 (7)	0.157 (6)	0.201 (8)	0.001 (5)	0.030 (6)	0.041 (6)
C23	0.158 (7)	0.105 (4)	0.113 (5)	−0.026 (4)	0.051 (5)	0.003 (4)

O1—C1	1.226 (4)	C11—C12	1.388 (4)
O2—C9	1.368 (4)	C11—H7	0.9300
O2—C13	1.411 (4)	C12—H8	0.9300
O3—C10	1.359 (4)	C13—H9	0.9600
O3—H12	0.8200	C13—H10	0.9600
O4—C17	1.351 (4)	C13—H11	0.9600
O4—C21	1.417 (4)	C14—C15	1.445 (4)
O5—C18	1.370 (4)	C14—H13	0.9300
O5—H20	0.8200	C15—C20	1.390 (4)
C1—C5	1.469 (4)	C15—C16	1.395 (4)
C1—C2	1.474 (4)	C16—C17	1.376 (4)
C2—C6	1.342 (4)	C16—H14	0.9300
C2—C3	1.493 (4)	C17—C18	1.394 (4)
C3—C4	1.553 (4)	C18—C19	1.365 (5)
C3—H1	0.9700	C19—C20	1.385 (4)
C3—H2	0.9700	C19—H15	0.9300
C4—C5	1.504 (5)	C20—H16	0.9300
C4—H3	0.9700	C21—H17	0.9600
C4—H4	0.9700	C21—H18	0.9600
C5—C14	1.349 (4)	C21—H19	0.9600
C6—C7	1.453 (4)	O6—C23	1.445 (7)
C6—H5	0.9300	O6—H26	0.8200
C7—C12	1.390 (4)	C22—C23	1.382 (7)
C7—C8	1.394 (4)	C22—H21	0.9600
C8—C9	1.378 (4)	C22—H22	0.9600
C8—H6	0.9300	C22—H23	0.9600
C9—C10	1.388 (5)	C23—H24	0.9700
C10—C11	1.366 (5)	C23—H25	0.9700
C9—O2—C13	118.0 (3)	O2—C13—H9	109.5
C10—O3—H12	109.5	O2—C13—H10	109.5
C17—O4—C21	118.1 (2)	H9—C13—H10	109.5
C18—O5—H20	109.5	O2—C13—H11	109.5
O1—C1—C5	125.3 (3)	H9—C13—H11	109.5
O1—C1—C2	126.3 (3)	H10—C13—H11	109.5
C5—C1—C2	108.4 (3)	C5—C14—C15	132.5 (3)
C6—C2—C1	118.9 (3)	C5—C14—H13	113.8
C6—C2—C3	131.6 (3)	C15—C14—H13	113.8
C1—C2—C3	109.5 (3)	C20—C15—C16	117.7 (3)
C2—C3—C4	106.6 (3)	C20—C15—C14	117.2 (3)
C2—C3—H1	110.4	C16—C15—C14	125.0 (3)
C4—C3—H1	110.4	C17—C16—C15	121.2 (3)
C2—C3—H2	110.4	C17—C16—H14	119.4
C4—C3—H2	110.4	C15—C16—H14	119.4
H1—C3—H2	108.6	O4—C17—C16	125.9 (3)
C5—C4—C3	105.6 (3)	O4—C17—C18	114.4 (3)
C5—C4—H3	110.6	C16—C17—C18	119.6 (3)
C3—C4—H3	110.6	C19—C18—O5	118.4 (3)
C5—C4—H4	110.6	C19—C18—C17	120.3 (3)
C3—C4—H4	110.6	O5—C18—C17	121.3 (3)
H3—C4—H4	108.7	C18—C19—C20	119.7 (3)
C14—C5—C1	118.7 (3)	C18—C19—H15	120.2
C14—C5—C4	131.5 (3)	C20—C19—H15	120.2
C1—C5—C4	109.8 (3)	C19—C20—C15	121.5 (3)
C2—C6—C7	132.3 (3)	C19—C20—H16	119.3
C2—C6—H5	113.8	C15—C20—H16	119.3
C7—C6—H5	113.8	O4—C21—H17	109.5
C12—C7—C8	118.3 (3)	O4—C21—H18	109.5
C12—C7—C6	117.4 (3)	H17—C21—H18	109.5
C8—C7—C6	124.3 (3)	O4—C21—H19	109.5
C9—C8—C7	120.6 (3)	H17—C21—H19	109.5
C9—C8—H6	119.7	H18—C21—H19	109.5
C7—C8—H6	119.7	C23—O6—H26	109.5
O2—C9—C8	126.1 (3)	C23—C22—H21	109.5
O2—C9—C10	113.8 (3)	C23—C22—H22	109.5
C8—C9—C10	120.1 (3)	H21—C22—H22	109.5
O3—C10—C11	118.2 (3)	C23—C22—H23	109.5
O3—C10—C9	121.5 (3)	H21—C22—H23	109.5
C11—C10—C9	120.3 (3)	H22—C22—H23	109.5
C10—C11—C12	119.7 (3)	C22—C23—O6	112.2 (5)
C10—C11—H7	120.1	C22—C23—H24	109.2
C12—C11—H7	120.1	O6—C23—H24	109.2
C11—C12—C7	121.0 (3)	C22—C23—H25	109.2
C11—C12—H8	119.5	O6—C23—H25	109.2
C7—C12—H8	119.5	H24—C23—H25	107.9
O1—C1—C2—C6	3.9 (6)	C8—C9—C10—C11	1.8 (6)
C5—C1—C2—C6	−177.1 (3)	O3—C10—C11—C12	−179.9 (3)
O1—C1—C2—C3	−175.8 (4)	C9—C10—C11—C12	−1.1 (6)
C5—C1—C2—C3	3.2 (4)	C10—C11—C12—C7	0.1 (6)
C6—C2—C3—C4	176.9 (4)	C8—C7—C12—C11	0.1 (5)
C1—C2—C3—C4	−3.5 (4)	C6—C7—C12—C11	−178.9 (3)
C2—C3—C4—C5	2.5 (4)	C1—C5—C14—C15	178.7 (4)
O1—C1—C5—C14	−2.1 (6)	C4—C5—C14—C15	−0.6 (7)
C2—C1—C5—C14	178.9 (3)	C5—C14—C15—C20	176.5 (4)
O1—C1—C5—C4	177.4 (4)	C5—C14—C15—C16	−4.7 (6)
C2—C1—C5—C4	−1.6 (4)	C20—C15—C16—C17	−0.4 (5)
C3—C4—C5—C14	178.8 (4)	C14—C15—C16—C17	−179.1 (3)
C3—C4—C5—C1	−0.6 (4)	C21—O4—C17—C16	−3.4 (5)
C1—C2—C6—C7	−177.4 (3)	C21—O4—C17—C18	177.1 (3)
C3—C2—C6—C7	2.2 (7)	C15—C16—C17—O4	−179.9 (3)
C2—C6—C7—C12	−177.9 (4)	C15—C16—C17—C18	−0.4 (5)
C2—C6—C7—C8	3.2 (6)	O4—C17—C18—C19	−179.8 (3)
C12—C7—C8—C9	0.6 (5)	C16—C17—C18—C19	0.7 (6)
C6—C7—C8—C9	179.5 (3)	O4—C17—C18—O5	0.0 (5)
C13—O2—C9—C8	3.8 (5)	C16—C17—C18—O5	−179.6 (3)
C13—O2—C9—C10	−175.2 (3)	O5—C18—C19—C20	180.0 (3)
C7—C8—C9—O2	179.5 (3)	C17—C18—C19—C20	−0.3 (6)
C7—C8—C9—C10	−1.6 (5)	C18—C19—C20—C15	−0.5 (6)
O2—C9—C10—O3	−0.4 (5)	C16—C15—C20—C19	0.8 (5)
C8—C9—C10—O3	−179.4 (3)	C14—C15—C20—C19	179.6 (3)
O2—C9—C10—C11	−179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H12···O2	0.82	2.21	2.653 (4)	114
O3—H12···O5i	0.82	2.13	2.802 (3)	139
O5—H20···O4	0.82	2.22	2.666 (3)	114
O5—H20···O6ii	0.82	1.93	2.682 (4)	151
O6—H26···O1iii	0.82	1.99	2.802 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H12⋯O2	0.82	2.21	2.653 (4)	114
O3—H12⋯O5i	0.82	2.13	2.802 (3)	139
O5—H20⋯O4	0.82	2.22	2.666 (3)	114
O5—H20⋯O6ii	0.82	1.93	2.682 (4)	151
O6—H26⋯O1iii	0.82	1.99	2.802 (4)	172

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