(2E,5E)-2,5-Bis(4-hy­droxy-3-meth­oxy­benzyl­idene)cyclo­penta­none ethanol monosolvate

Da'i, M.; Yanuar, A.; Meiyanto, E.; Jenie, U.A.; Supardjan, A.M.

doi:10.1107/S1600536813005229

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o530

doi:10.1107/S1600536813005229

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(2E,5E)-2,5-Bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone ethanol monosolvate

Muhammad Da'i,^a Arry Yanuar,^b ^* Edy Meiyanto,^c Umar Anggara Jenie ^c and Amir Margono Supardjan ^c

^aFaculty of Pharmacy, Muhammadiyah University, Jl. A. Yani Tromol Pos I Pabelan, Kartosuro, Surakarta 57162, Indonesia, ^bFaculty of Pharmacy, University of Indonesia, Kampus Universitas Indonesia, Depok 16424, Indonesia, and ^cFaculty of Pharmacy, Gadjah Mada University, Sekip Utara, Yogyakarta 55281, Indonesia
^*Correspondence e-mail: arry.yanuar@ui.ac.id

(Received 14 December 2012; accepted 23 February 2013; online 13 March 2013)

In the title structure, C₂₁H₂₀O₅·C₂H₅OH, the curcumine-type molecule has a double E conformation for the two benzylidene 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 intramolecular branches to adjacent methoxy O atoms and intermolecular branches to either a neighbouring molecule or an ethanol solvent molecule. 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_r = 398.45
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.157
S = 1.00
3720 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005229/qk2050sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813005229/qk2050Isup3.mol

Supporting information file. DOI: 10.1107/S1600536813005229/qk2050Isup4.cml

checkCIF report

Comment top

The title structure contains a curcumin analogue synthesized from vanillin (4-hydroxy-3-methoxybenzaldehyde) and cyclopentanone using acidic catalysis (Sardjiman et al., 1997). This curcumin analogue showed good activities as anticancer agent in T47D cell line tests, and has also antioxidant and anti-inflammatory properties (Ohori et al., 2006; Da'i et al., 2007; Anand et al., 2008). As an extension of the work on this compound (Sardjiman et al., 1997; Da'i et al., 2007) we report here the crystal structure of (I), an ethanol solvate. The curcumin type molecule contains two double bonds between C2 and C6 and C5 and C14 which connect the cyclopentanone fragment to the 4-hydroxy-3-methoxybenzylidene groups in E configuration relative to the carbonyl group. The entire molecule is essentially planar with respect to non-hydrogen atoms. The keto-diene system shows usual bond distances and angles. While the angles C1—C2=C6 = 118.9 (3)° and C1—C5=C14 = 118.7 (3)° are close to the ideal C_sp2 bond angle of 120°, the bond angles C2=C6—C7 = 132.3 (3)° and C5=C14—C15 = 132.5 (3)° are large in response to intramolecular H···H contacts (phenyl H6 and H14 with the C₂H₄ group of the cyclopentanone ring). A partial conjugation between the C2=C6 and C5=C14 double bonds and the carbonyl group C1=O1 is evident from the bond lengths table. All other bond lengths and angles adopt usual values (Du et al., 2010, 2011). In the crystal structure the curcumin type molecules are oriented approximately parallel to (203) and form together with the ethanol solvent molecules layer-like assemblies parallel to (101) linked via hydrogen bonds (Table 1). The two phenolic OH groups form bifurcated hydrogen bonds with intramolecular branches to adjacent methoxy O atoms (O3—H12···O5, O5—H20···O4) and intermolecular branches to either a neigbour molecule (O3—H12···O5ⁱ) or an ethanol molecule (O5—H20···O6ⁱⁱ). Ethanol donates a hydrogen bond to the keto-oxygen atom.

Related literature top

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 top

The compound was synthesized according to Sardjiman et al. (1997). It was then dissolved in boiling ethanol and crystallized by slow cooling giving yellowish crystals that were stored in cold ethanol prior to X-ray analysis.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); 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).

Figures top

	Fig. 1. The asymmetric unit of (I), with the atomic numbering scheme. The thermal ellipsoids are scaled to 50% probability level.
	Fig. 2. Crystal packing of the title compound.

(2E,5E)-2,5-Bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone ethanol monosolvate top

Crystal data top

C₂₁H₂₀O₅·C₂H₆O	F(000) = 848.00
M_r = 398.45	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0566P)² + 0.4936P] where P = (F_o² + 2F_c²)/3
3720 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₂₀O₅·C₂H₆O	V = 2053.4 (13) Å³
M_r = 398.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.880 (4) Å	µ = 0.09 mm⁻¹
b = 17.050 (5) Å	T = 296 K
c = 13.950 (5) Å	0.12 × 0.10 × 0.06 mm
β = 103.527 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3720 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	1748 reflections with I > 2σ(I)
T_min = 0.671, T_max = 0.994	R_int = 0.119
16083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	Δρ_max = 0.14 e Å⁻³
3720 reflections	Δρ_min = −0.21 e Å⁻³
268 parameters

Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀O₅·C₂H₆O
M_r	398.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.880 (4), 17.050 (5), 13.950 (5)
β (°)	103.527 (14)
V (Å³)	2053.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.671, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	16083, 3720, 1748
R_int	0.119
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.157, 1.00
No. of reflections	3720
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21

Computer programs: RAPID-AUTO (Rigaku, 2006), SIR2008 (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H12···O2	0.82	2.21	2.653 (4)	114.3
O3—H12···O5ⁱ	0.82	2.13	2.802 (3)	139.3
O5—H20···O4	0.82	2.22	2.666 (3)	114.0
O5—H20···O6ⁱⁱ	0.82	1.93	2.682 (4)	151.1
O6—H26···O1ⁱⁱⁱ	0.82	1.99	2.802 (4)	172.1

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1.

Acknowledgements

The authors thank Mrs Sachiko Iida (Iida Group Foundation, Japan) for funding, Professor Masashi Kawaichi for providing access to his laboratory for MD, and NAIST (Nara Institute of Science and Technology), Japan, for access to the X-ray facility.

References

Anand, P., Thomas, S. G., Kunnumakkara, A. B., Sundaram, C., Harikumar, K. B., Sung, B., Tharakan, S. T., Misra, K., Priyadarsini, I. K., Rajasekharan, K. N. & Agarwal, B. B. (2008). Biochem. Pharmacol. 76, 1590–1611. Web of Science CrossRef PubMed CAS Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. Web of Science CrossRef CAS IUCr Journals Google Scholar
Da'i, M., Supardjan, A. M., Meiyanto, E. & Jenie, U. A. (2007). Majalah Farmasi Indonesia, 18, 40–47. Google Scholar
Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2010). Acta Cryst. E66, o3334. Web of Science CSD CrossRef IUCr Journals Google Scholar
Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2011). Acta Cryst. E67, o116. Web of Science CrossRef IUCr Journals Google Scholar
Ohori, M., Yamakoshi, H., Tomozawa, M., Shibuya, M., Kakudo, Y., Takahashi, A., Takahashi, S., Kato, S., Suzuki, T., Ishioka, C., Iwabuchi, Y. & Shibata, H. (2006). Mol. Cancer Ther. 5, 2563–2571. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2006). RAPID AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sardjiman, S. S., Reksohadiprodjo, M. S., Hakim, L., Van Der Goot, H. & Timmerman, H. (1997). Eur. J. Med. Chem. 32, 625–630. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o530

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E,5E)-2,5-Bis(4-hy­dr­oxy-3-meth­­oxy­benzyl­­idene)cyclo­penta­none ethanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2E,5E)-2,5-Bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone ethanol monosolvate