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Volume 69 
Part 4 
Page o530  
April 2013  

Received 14 December 2012
Accepted 23 February 2013
Online 13 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.070
wR = 0.157
Data-to-parameter ratio = 13.9
Details
Open access

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

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

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[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.]); Da'i et al. (2007[Da'i, M., Supardjan, A. M., Meiyanto, E. & Jenie, U. A. (2007). Majalah Farmasi Indonesia, 18, 40-47.]); Anand et al. (2008[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.]). For the synthesis of the title compound, see: Sardjiman et al. (1997[Sardjiman, S. S., Reksohadiprodjo, M. S., Hakim, L., Van Der Goot, H. & Timmerman, H. (1997). Eur. J. Med. Chem. 32, 625-630.]). For related structures, see: Du et al. (2010[Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2010). Acta Cryst. E66, o3334.], 2011[Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2011). Acta Cryst. E67, o116.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20O5·C2H6O

  • Mr = 398.45

  • Monoclinic, P 21 /n

  • a = 8.880 (4) Å

  • b = 17.050 (5) Å

  • c = 13.950 (5) Å

  • [beta] = 103.527 (14)°

  • V = 2053.4 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.671, Tmax = 0.994

  • 16083 measured reflections

  • 3720 independent reflections

  • 1748 reflections with I > 2[sigma](I)

  • Rint = 0.119

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.157

  • S = 1.00

  • 3720 reflections

  • 268 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]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[Rigaku (2006). RAPID AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 (Burla et al., 2007[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2050 ).


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.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Da'i, M., Supardjan, A. M., Meiyanto, E. & Jenie, U. A. (2007). Majalah Farmasi Indonesia, 18, 40-47.
Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2010). Acta Cryst. E66, o3334.  [CSD] [CrossRef] [details]
Du, Z.-Y., Huang, H.-R., Lu, Y.-J., Zhang, K. & Fang, Y.-X. (2011). Acta Cryst. E67, o116.  [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). RAPID AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sardjiman, S. S., Reksohadiprodjo, M. S., Hakim, L., Van Der Goot, H. & Timmerman, H. (1997). Eur. J. Med. Chem. 32, 625-630.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o530  [ doi:10.1107/S1600536813005229 ]

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