PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3334.
Published online 2010 November 27. doi:  10.1107/S1600536810041930
PMCID: PMC3011648

(3E,5E)-3,5-Bis(4-hy­droxy-3,5-di­methoxy­benzyl­idene)oxan-4-one monohydrate

Abstract

In the title compound, C23H24O8·H2O, the six-membered ring of the oxan-4-one (tetra­hydro­pyran-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 [triangle]). The title compound is used in the preparation of curcumin analogues, see: Du et al. (2006a [triangle],b [triangle]); Liu et al. (2008 [triangle]). For a related structure, see: Abaee et al. (2008 [triangle]). For the synthesis, see: Du et al. (2006a [triangle],b [triangle]); Youssef et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3334-scheme1.jpg

Experimental

Crystal data

  • C23H24O8·H2O
  • M r = 446.44
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3334-efi7.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 1999 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

We thank the projects of China National Natural Science Funds, Guangdong Provincial Science Foundation and the 211 Project of Guangdong Province, China.

supplementary crystallographic information

Comment

Curcumin possesses a wide spectrum of pharmacological activities including anti-oxidant, anti-inflammatory, antiviral, antifungal, cancer chemo preventive, cancer chemotherapeutic properties etc. (Maheshwari et al., 2006). We ever screened curcumin analogues for aldose reductase (Du et al., 2006a), α-glucosidase (Du et al., 2006b) and thioredoxin reductase inhibition (Liu et al., 2008). This class of compounds is readily synthesized by reacting a substituted benzaldehyde with tetrahydropyran-4-one; in the case of the title compound, 4-hydroxy-3,5-dimethoxybenzaldehyde was used as the reactant.

The molecular structure of the title compound contains the two 4-hydroxy-3,5-dimethoxyphenyl substituents on the tetrahydropyran-4-one, and the six-membered hetero-ring adopts an envelope conformation with the flap oxygen atom displaced by 0.682 (10) Å from the plane of the other five atoms (Figure 1).

Similar structures have been observed in the literature (Abaee et al., 2008; Du et al., 2006a,b).

The dihedral angles formed between the mean plane through the six atoms of the pyranone ring and two benzene rings of 4-hydroxy-3,5-dimethoxyphenyl groups are 53.86 (10) and 27.86 (10)°, the corresponding dihedral angles between two benzene rings of 4-hydroxy-3,5-dimethoxyphenyl groups is 37.23 (10) °.

In the crystal packing, the molecules are linked by intermolecular O—H···O hydrogen bonds into one-dimensional zigzag chain along b axis (Figure 2, table 1), and through water molecules further connecting into a supramolecular three-dimensional complicated hydrogen bonding network (Figure 3, table 1).

Experimental

The title compound was synthesized using a general procedure (Du et al., 2006a,b; Youssef et al., 2004). 4-Hydroxy-3,5-dimethoxybenzy (0.01 mol) and tetrahydropyran-4-one (0.005 mol) were dissolved in THF and added 0.5 mL concentrated HCl as catalyst. The mixture was warmed at 298-303 K for 24 h, cold water was added to precipitate the yellow compound. Crystals were obtained by recrystallization from THF solution.

Refinement

The C-bound H atoms were positioned geometrically and were included in the refinement in the riding-model approximation, with C—H = 0.96 (CH3), 0.97 (CH2) and 0.93 Å (aromatic); Uiso(H) = 1.2Ueq(C) for H atoms on secondary and tertiary C atoms, and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The water and hydroxyl H atoms were located in a difference Fourier map and refined as riding with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
Perspective view showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The molecules are linked via intermolecular O—H···O hydrogen bonds into one-dimensional zigzag chain along b axis. Hydrogen bonds are shown as dashed lines. Symmetry: A = -x + 2, y - 1/2, -z + 3/2; B = -x + 2, y + 1/2, ...
Fig. 3.
The one-dimensional zigzag chain are connected by water hydrogen bonds into a supramolecular three-dimensional complicated hydrogen bonding network. Hydrogen bonds are shown as dashed lines. Symmetry: C = -x + 1, y + 1/2, -z + 3/2; D = -x + 1, -y + 1, ...

Crystal data

C23H24O8·H2OF(000) = 944
Mr = 446.44Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3096 reflections
a = 9.203 (2) Åθ = 2.7–25.5°
b = 14.145 (3) ŵ = 0.11 mm1
c = 17.011 (4) ÅT = 293 K
β = 105.349 (5)°Block, pale yellow
V = 2135.5 (9) Å30.43 × 0.40 × 0.32 mm
Z = 4

Data collection

Bruker SMART CCD 1000 area-detector diffractometer4650 independent reflections
Radiation source: fine-focus sealed tube2502 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 27.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.955, Tmax = 0.967k = −17→18
12756 measured reflectionsl = −12→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3
4650 reflections(Δ/σ)max < 0.001
295 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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.

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

xyzUiso*/Ueq
C10.8908 (2)0.32659 (13)0.97171 (12)0.0394 (5)
C20.8037 (2)0.29050 (13)1.02728 (12)0.0394 (5)
C30.6896 (2)0.35663 (14)1.04616 (13)0.0473 (6)
H3A0.61470.32071.06430.057*
H3B0.73900.39941.08960.057*
C40.7220 (2)0.47300 (14)0.95381 (15)0.0498 (6)
H4A0.76000.51660.99850.060*
H4B0.67010.50960.90650.060*
C50.8524 (2)0.42155 (13)0.93530 (12)0.0392 (5)
C60.8228 (2)0.19984 (14)1.05100 (13)0.0455 (5)
H60.89200.16581.03110.055*
C70.7496 (2)0.14758 (13)1.10385 (13)0.0417 (5)
C80.7119 (2)0.05293 (13)1.08579 (14)0.0452 (5)
H80.74180.02331.04380.054*
C90.6305 (2)0.00271 (13)1.12948 (13)0.0427 (5)
C100.5885 (2)0.04587 (13)1.19366 (13)0.0403 (5)
C110.6329 (2)0.13891 (14)1.21437 (13)0.0398 (5)
C120.7122 (2)0.18956 (14)1.16978 (13)0.0428 (5)
H120.74060.25171.18390.051*
C130.9318 (2)0.45266 (13)0.88503 (13)0.0410 (5)
H131.00800.41160.88050.049*
C140.9230 (2)0.53765 (13)0.83608 (13)0.0395 (5)
C150.9862 (2)0.53228 (13)0.77028 (13)0.0422 (5)
H151.03420.47710.76130.051*
C160.9781 (2)0.60806 (13)0.71856 (13)0.0410 (5)
C170.9098 (2)0.69190 (13)0.73198 (13)0.0401 (5)
C180.8509 (2)0.69876 (13)0.79906 (13)0.0406 (5)
C190.8556 (2)0.62257 (13)0.85041 (13)0.0408 (5)
H190.81400.62760.89450.049*
C200.6271 (3)−0.13737 (15)1.05107 (15)0.0607 (7)
H20A0.5826−0.10710.99980.091*
H20B0.5931−0.20171.04900.091*
H20C0.7349−0.13621.06160.091*
C210.6141 (3)0.26902 (15)1.30040 (16)0.0681 (7)
H21A0.72040.28161.31470.102*
H21B0.57470.28351.34590.102*
H21C0.56460.30751.25470.102*
C221.1153 (3)0.53010 (16)0.63678 (16)0.0637 (7)
H22A1.20070.52150.68290.096*
H22B1.14930.54050.58880.096*
H22C1.05300.47460.62950.096*
C230.7318 (3)0.79786 (15)0.87680 (15)0.0583 (6)
H23A0.65180.75340.87410.088*
H23B0.69360.86100.87680.088*
H23C0.81040.78750.92590.088*
O10.99167 (17)0.27831 (9)0.95636 (9)0.0512 (4)
O20.61814 (16)0.40948 (10)0.97496 (10)0.0530 (4)
O30.58409 (18)−0.08894 (9)1.11397 (10)0.0589 (4)
O40.50522 (17)−0.00394 (9)1.23443 (10)0.0535 (4)
H40.47510.03161.26480.080*
O50.58841 (17)0.17232 (9)1.27958 (9)0.0524 (4)
O61.03097 (17)0.60926 (9)0.65026 (10)0.0564 (4)
O70.89910 (18)0.76810 (9)0.68224 (10)0.0527 (4)
H70.94090.75640.64630.079*
O80.79014 (17)0.78551 (9)0.80853 (10)0.0547 (4)
O1W0.65172 (17)0.92850 (11)0.65729 (11)0.0660 (5)
H1A0.70020.87800.67590.099*
H1B0.58490.91420.61190.099*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0492 (13)0.0356 (11)0.0326 (12)−0.0025 (10)0.0094 (11)−0.0033 (9)
C20.0479 (12)0.0356 (11)0.0354 (13)−0.0017 (9)0.0120 (11)−0.0005 (9)
C30.0536 (13)0.0463 (12)0.0442 (14)0.0021 (10)0.0167 (12)0.0079 (11)
C40.0552 (14)0.0403 (12)0.0554 (15)0.0015 (10)0.0173 (12)0.0078 (11)
C50.0464 (12)0.0338 (11)0.0369 (13)−0.0033 (9)0.0103 (11)0.0004 (9)
C60.0536 (13)0.0404 (12)0.0456 (14)−0.0003 (10)0.0185 (12)0.0013 (10)
C70.0470 (12)0.0374 (11)0.0423 (13)0.0022 (10)0.0149 (11)0.0071 (10)
C80.0551 (13)0.0378 (11)0.0467 (14)0.0045 (10)0.0204 (12)0.0045 (10)
C90.0487 (12)0.0310 (11)0.0483 (14)0.0017 (9)0.0129 (11)0.0028 (10)
C100.0416 (11)0.0368 (11)0.0433 (13)0.0022 (9)0.0126 (11)0.0078 (10)
C110.0445 (12)0.0389 (11)0.0364 (13)0.0032 (9)0.0111 (11)0.0024 (10)
C120.0494 (12)0.0343 (11)0.0435 (14)−0.0008 (9)0.0102 (11)0.0038 (10)
C130.0500 (12)0.0321 (10)0.0410 (13)−0.0001 (9)0.0121 (11)0.0013 (10)
C140.0433 (11)0.0321 (10)0.0429 (13)−0.0024 (9)0.0112 (11)0.0011 (9)
C150.0461 (12)0.0323 (11)0.0497 (14)−0.0002 (9)0.0155 (11)0.0020 (10)
C160.0436 (12)0.0383 (11)0.0453 (14)−0.0017 (9)0.0190 (11)0.0019 (10)
C170.0437 (12)0.0323 (11)0.0451 (14)−0.0015 (9)0.0133 (11)0.0064 (10)
C180.0448 (12)0.0292 (11)0.0488 (14)0.0020 (9)0.0140 (11)0.0007 (10)
C190.0475 (12)0.0362 (11)0.0415 (13)−0.0030 (9)0.0167 (11)0.0008 (10)
C200.0782 (17)0.0438 (13)0.0601 (17)0.0027 (12)0.0184 (14)−0.0078 (12)
C210.094 (2)0.0520 (15)0.0655 (18)−0.0044 (13)0.0329 (16)−0.0146 (13)
C220.0762 (17)0.0526 (14)0.0759 (19)0.0133 (12)0.0440 (16)0.0072 (13)
C230.0667 (15)0.0494 (13)0.0644 (17)0.0141 (11)0.0269 (14)0.0014 (12)
O10.0681 (10)0.0414 (8)0.0521 (10)0.0110 (7)0.0299 (9)0.0080 (7)
O20.0484 (9)0.0532 (9)0.0581 (10)0.0032 (7)0.0155 (8)0.0173 (8)
O30.0842 (11)0.0372 (8)0.0632 (11)−0.0119 (8)0.0334 (10)−0.0059 (8)
O40.0651 (10)0.0424 (8)0.0620 (12)−0.0067 (7)0.0328 (9)0.0020 (8)
O50.0698 (10)0.0421 (8)0.0523 (10)−0.0040 (7)0.0285 (9)−0.0043 (7)
O60.0751 (11)0.0425 (8)0.0638 (11)0.0120 (7)0.0399 (10)0.0117 (8)
O70.0715 (11)0.0363 (8)0.0578 (11)0.0075 (7)0.0303 (9)0.0122 (8)
O80.0743 (11)0.0387 (8)0.0598 (11)0.0117 (7)0.0328 (9)0.0061 (7)
O1W0.0629 (10)0.0578 (10)0.0766 (13)−0.0020 (8)0.0171 (9)0.0005 (9)

Geometric parameters (Å, °)

C1—O11.234 (2)C15—C161.376 (3)
C1—C51.482 (3)C15—H150.9300
C1—C21.483 (3)C16—O61.374 (2)
C2—C61.342 (3)C16—C171.389 (3)
C2—C31.503 (3)C17—O71.358 (2)
C3—O21.427 (2)C17—C181.390 (3)
C3—H3A0.9700C18—O81.376 (2)
C3—H3B0.9700C18—C191.381 (3)
C4—O21.426 (2)C19—H190.9300
C4—C51.506 (3)C20—O31.413 (3)
C4—H4A0.9700C20—H20A0.9600
C4—H4B0.9700C20—H20B0.9600
C5—C131.338 (3)C20—H20C0.9600
C6—C71.460 (3)C21—O51.417 (2)
C6—H60.9300C21—H21A0.9600
C7—C121.390 (3)C21—H21B0.9600
C7—C81.397 (3)C21—H21C0.9600
C8—C91.383 (3)C22—O61.415 (2)
C8—H80.9300C22—H22A0.9600
C9—O31.369 (2)C22—H22B0.9600
C9—C101.392 (3)C22—H22C0.9600
C10—O41.358 (2)C23—O81.413 (3)
C10—C111.395 (3)C23—H23A0.9600
C11—O51.365 (2)C23—H23B0.9600
C11—C121.384 (3)C23—H23C0.9600
C12—H120.9300O4—H40.8200
C13—C141.452 (3)O7—H70.8200
C13—H130.9300O1W—H1A0.8572
C14—C151.393 (3)O1W—H1B0.8743
C14—C191.403 (3)
O1—C1—C5121.49 (18)C16—C15—C14120.50 (18)
O1—C1—C2120.54 (17)C16—C15—H15119.8
C5—C1—C2117.97 (18)C14—C15—H15119.8
C6—C2—C1118.06 (18)O6—C16—C15125.38 (18)
C6—C2—C3125.04 (19)O6—C16—C17113.92 (17)
C1—C2—C3116.64 (17)C15—C16—C17120.70 (19)
O2—C3—C2109.61 (17)O7—C17—C16122.48 (19)
O2—C3—H3A109.7O7—C17—C18118.44 (17)
C2—C3—H3A109.7C16—C17—C18119.08 (18)
O2—C3—H3B109.7O8—C18—C19124.58 (19)
C2—C3—H3B109.7O8—C18—C17114.67 (17)
H3A—C3—H3B108.2C19—C18—C17120.75 (18)
O2—C4—C5111.89 (16)C18—C19—C14119.97 (19)
O2—C4—H4A109.2C18—C19—H19120.0
C5—C4—H4A109.2C14—C19—H19120.0
O2—C4—H4B109.2O3—C20—H20A109.5
C5—C4—H4B109.2O3—C20—H20B109.5
H4A—C4—H4B107.9H20A—C20—H20B109.5
C13—C5—C1117.08 (18)O3—C20—H20C109.5
C13—C5—C4125.08 (18)H20A—C20—H20C109.5
C1—C5—C4117.74 (17)H20B—C20—H20C109.5
C2—C6—C7128.60 (19)O5—C21—H21A109.5
C2—C6—H6115.7O5—C21—H21B109.5
C7—C6—H6115.7H21A—C21—H21B109.5
C12—C7—C8119.13 (19)O5—C21—H21C109.5
C12—C7—C6122.26 (18)H21A—C21—H21C109.5
C8—C7—C6118.58 (19)H21B—C21—H21C109.5
C9—C8—C7120.8 (2)O6—C22—H22A109.5
C9—C8—H8119.6O6—C22—H22B109.5
C7—C8—H8119.6H22A—C22—H22B109.5
O3—C9—C8124.67 (19)O6—C22—H22C109.5
O3—C9—C10115.41 (18)H22A—C22—H22C109.5
C8—C9—C10119.92 (18)H22B—C22—H22C109.5
O4—C10—C9118.97 (18)O8—C23—H23A109.5
O4—C10—C11121.84 (19)O8—C23—H23B109.5
C9—C10—C11119.19 (19)H23A—C23—H23B109.5
O5—C11—C12125.57 (18)O8—C23—H23C109.5
O5—C11—C10113.63 (17)H23A—C23—H23C109.5
C12—C11—C10120.8 (2)H23B—C23—H23C109.5
C11—C12—C7120.00 (19)C4—O2—C3110.80 (16)
C11—C12—H12120.0C9—O3—C20118.01 (17)
C7—C12—H12120.0C10—O4—H4109.5
C5—C13—C14132.99 (19)C11—O5—C21118.12 (17)
C5—C13—H13113.5C16—O6—C22117.36 (16)
C14—C13—H13113.5C17—O7—H7109.5
C15—C14—C19118.95 (18)C18—O8—C23117.46 (16)
C15—C14—C13116.33 (18)H1A—O1W—H1B108.0
C19—C14—C13124.71 (19)
O1—C1—C2—C6−9.1 (3)C6—C7—C12—C11175.20 (19)
C5—C1—C2—C6170.58 (19)C1—C5—C13—C14176.8 (2)
O1—C1—C2—C3176.48 (19)C4—C5—C13—C140.4 (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—C1921.6 (4)
C1—C2—C3—O237.7 (2)C19—C14—C15—C16−2.2 (3)
O1—C1—C5—C130.0 (3)C13—C14—C15—C16177.47 (18)
C2—C1—C5—C13−179.67 (18)C14—C15—C16—O6−177.28 (19)
O1—C1—C5—C4176.63 (19)C14—C15—C16—C171.5 (3)
C2—C1—C5—C4−3.1 (3)O6—C16—C17—O7−0.9 (3)
O2—C4—C5—C13152.0 (2)C15—C16—C17—O7−179.78 (19)
O2—C4—C5—C1−24.3 (3)O6—C16—C17—C18179.54 (18)
C1—C2—C6—C7−179.0 (2)C15—C16—C17—C180.7 (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—O8178.00 (18)
C2—C6—C7—C8142.7 (2)O7—C17—C18—C19178.38 (19)
C12—C7—C8—C93.9 (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—O3177.48 (19)C17—C18—C19—C141.3 (3)
C7—C8—C9—C10−1.6 (3)C15—C14—C19—C180.8 (3)
O3—C9—C10—O4−0.8 (3)C13—C14—C19—C18−178.80 (19)
C8—C9—C10—O4178.29 (19)C5—C4—O2—C360.9 (2)
O3—C9—C10—C11179.12 (18)C2—C3—O2—C4−67.7 (2)
C8—C9—C10—C11−1.7 (3)C8—C9—O3—C202.7 (3)
O4—C10—C11—O51.7 (3)C10—C9—O3—C20−178.19 (19)
C9—C10—C11—O5−178.28 (18)C12—C11—O5—C215.3 (3)
O4—C10—C11—C12−177.24 (19)C10—C11—O5—C21−173.58 (19)
C9—C10—C11—C122.8 (3)C15—C16—O6—C22−7.4 (3)
O5—C11—C12—C7−179.31 (18)C17—C16—O6—C22173.82 (19)
C10—C11—C12—C7−0.5 (3)C19—C18—O8—C231.6 (3)
C8—C7—C12—C11−2.8 (3)C17—C18—O8—C23−178.42 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···O1Wi0.822.062.833 (2)156
O7—H7···O1ii0.822.032.801 (2)157
O1W—H1A···O70.862.383.162 (2)152
O1W—H1B···O2iii0.872.052.888 (2)160
C13—H13···O7iv0.932.543.390 (3)151
C23—H23C···O1v0.962.503.445 (3)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5053).

References

  • Abaee, M. S., Mojtahedi, M. M., Sharifi, R., Zahedi, M. M., Mesbah, A. W. & Massa, W. (2008). J. Chem. Res. pp. 388–389.
  • Bruker (1999). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Du, Z.-Y., Bao, Y.-D., Liu, Z., Mao, X.-P., Ma, L., Huang, Z.-S., Gu, L.-Q. & Chan, A. S. C. (2006a). Arch. Pharm. (Weinheim), 339, 123–128. [PubMed]
  • Du, Z.-Y., Liu, R.-R., Shao, W.-Y., Mao, X.-P., Ma, L., Gu, L.-Q. & Huang, Z.-S. (2006b). Eur. J. Med. Chem.42, 213–218. [PubMed]
  • Liu, Z., Du, Z.-Y., Huang, Z.-S., Lee, K. S. & Gu, L.-Q. (2008). Biosci. Biotech. Biochem.72, 2214–2218. [PubMed]
  • Maheshwari, R. K., Singh, A. K., Gaddipati, J. & Srimal, R. C. (2006). Life Sci.78, 2081–2087. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Youssef, K. M., El-Sherbeny, M. A., El-Shafie, F. S., Farag, H. A., Al-Deeb, O. A. & Awadalla, S. A. (2004). Arch. Pharm. Pharm. Med. Chem.337, 42–54. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography