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Volume 69 
Part 9 
Page o1474  
September 2013  

Received 29 July 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.095
Data-to-parameter ratio = 15.2
Details
Open access

Ethyl (2Z)-3-oxo-2-(3,4,5-trimethoxybenzylidene)butanoate

aDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil,bInstituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas, SP, Brazil,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: julio@power.ufscar.br

In the title compound, C16H20O6, the conformation about the C=C double bond [1.344 (2) Å] is Z. With respect to this bond, the ketone is almost coplanar [C-C-C-O torsion angle = -179.60 (10)°] and the ester is almost perpendicular [C-C-C-O = 78.42 (13)°]. The methoxy substituents of the central benzene ring are either almost coplanar [C-C-O-C = 3.54 (15) and 177.70 (9)°] or perpendicular [C-C-O-C = 80.08 12)° for the central substituent]. In the crystal, the three-dimensional architecture features C-H...O and [pi]-[pi] [inter-centroid distance = 3.6283 (6) Å] interactions.

Related literature

For background to the study, see: Rodrigues et al. (2004[Rodrigues, J. A. R., Moran, P. J. S., Conceicão, G. J. A. & Fardelone, L. C. (2004). Food Technol. Biotechnol. 42, 295-303.]); Zukerman-Schpector et al. (2011[Zukerman-Schpector, J., Abd Salim, S. N., Moran, P. J. S., Paula, B. R. S. de, Rodrigues, J. A. R. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1044.]). For the synthesis of the title compound, see: de Paula (2012[Paula, B. R. S. de (2012). MSc thesis, Universidade de Campinas, UNICAMP, Brazil.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20O6

  • Mr = 308.32

  • Triclinic, [P \overline 1]

  • a = 8.3432 (4) Å

  • b = 10.2446 (5) Å

  • c = 10.4543 (5) Å

  • [alpha] = 61.130 (5)°

  • [beta] = 77.450 (4)°

  • [gamma] = 82.534 (4)°

  • V = 763.48 (7) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.86 mm-1

  • T = 100 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.]) Tmin = 0.631, Tmax = 1.000

  • 5294 measured reflections

  • 3101 independent reflections

  • 2943 reflections with I > 2[sigma](I)

  • Rint = 0.012

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.095

  • S = 1.05

  • 3101 reflections

  • 204 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12b...O5i 0.97 2.47 3.4390 (16) 174
C14-H14a...O4ii 0.96 2.52 3.3295 (16) 142
C16-H16c...O2iii 0.96 2.55 3.4863 (15) 165
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+2, -z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and MarvinSketch (ChemAxon, 2010[ChemAxon (2010). Marvinsketch. http://www.chemaxon.com.]); 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: KJ2231 ).


Acknowledgements

We thank the Brazilian agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq: 306532/2009-3,to JZ-S), Coordenação de Aperfeicoamento de Pessoal de Nível Superior (CAPES: 808/09 to JZ-S and scholarship to CLH) and FAPESP for financial support. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Santa Clara, CA, USA.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
ChemAxon (2010). Marvinsketch. http://www.chemaxon.com.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Paula, B. R. S. de (2012). MSc thesis, Universidade de Campinas, UNICAMP, Brazil.
Rodrigues, J. A. R., Moran, P. J. S., Conceicão, G. J. A. & Fardelone, L. C. (2004). Food Technol. Biotechnol. 42, 295-303.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zukerman-Schpector, J., Abd Salim, S. N., Moran, P. J. S., Paula, B. R. S. de, Rodrigues, J. A. R. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1044.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1474  [ doi:10.1107/S1600536813023374 ]

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