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Volume 69 
Part 8 
Page o1231  
August 2013  

Received 28 June 2013
Accepted 3 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.104
Data-to-parameter ratio = 16.4
Details
Open access

Ethyl (Z)-4'-(4-ethoxy-1-hydroxy-3,4-dioxobut-1-en-1-yl)-[1,1'-biphenyl]-3-carboxylate

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

The 1,3-diketone group of the title compound, C21H20O6, exists in a keto-enol form stabilized by a strong intramolecular O-H...O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C-O and C-C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, molecules are packed in a layered structure parallel to the b axis through C-H...O and [pi]-[pi] interactions [centroid-centroid distance between stacked benzene rings = 3.868 (2) Å].

Related literature

For background to this study, see: Ishikawa & Fujii (2011[Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.]). For related structures, see: Wang et al. (2008[Wang, J., Zhou, W. & Xu, W.-G. (2008). Acta Cryst. E64, o15.]); Pillay et al. (2013[Pillay, A., Khorasani, S. & de Koning, C. B. (2013). Acta Cryst. E69, o54-o55.]). For the biological activity of related compounds, see: Tomassini et al. (1994[Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20O6

  • Mr = 368.39

  • Monoclinic, C 2/c

  • a = 26.572 (16) Å

  • b = 12.194 (5) Å

  • c = 11.213 (6) Å

  • [beta] = 96.03 (5)°

  • V = 3613 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.50 × 0.45 × 0.30 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.707, Tmax = 0.971

  • 4944 measured reflections

  • 4109 independent reflections

  • 2874 reflections with F2 > 2[sigma](F2)

  • Rint = 0.029

  • 3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.01

  • 4109 reflections

  • 250 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H14...O4 0.98 (3) 1.61 (3) 2.522 (2) 152 (3)

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; 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: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2109 ).


Acknowledgements

This work was partly supported by Grants-in-Aid (No. 24590141 to YI) for Scientific Research from the Japan Society for the Promotion of Science. We acknowledge the University of Shizuoka for supporting this study.

References

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] [ChemPort] [IUCr Journals]
Ishikawa, Y. & Fujii, S. (2011). Bioinformation, 6, 221-225.  [CrossRef] [PubMed]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Pillay, A., Khorasani, S. & de Koning, C. B. (2013). Acta Cryst. E69, o54-o55.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tomassini, J., Selnick, H., Davies, M. E., Armstrong, M. E., Baldwin, J., Bourgeois, M., Hastings, J., Hazuda, D., Lewis, J., McClements, W., Ponticello, G., Radzilowski, E., Smith, G., Tebben, A. & Wolfe, A. (1994). Antimicrob. Agents Chemother. 38, 2827-2837.  [CrossRef] [ChemPort] [PubMed]
Wang, J., Zhou, W. & Xu, W.-G. (2008). Acta Cryst. E64, o15.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1231  [ doi:10.1107/S1600536813018503 ]

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