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Volume 69 
Part 6 
Page o919  
June 2013  

Received 28 April 2013
Accepted 7 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.136
Data-to-parameter ratio = 15.0
Details
Open access

Dimethyl 2-(4-methylbenzylidene)malonate

aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia,bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia 21321 Alexandria, Egypt, and cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the molecule of the title compound, C13H14O4, the benzene ring forms dihedral angles of 18.60 (7) and 81.36 (8)° with the two arms of the malonate moiety. The crystal structure features C-H...O interactions, which form chains running parallel to the b axis.

Related literature

For the biological activity and synthesis of alkylidene and arylidene malonates, see: Liu et al. (2012[Liu, L., Sarkisian, R., Xu, Z. & Wang, H. (2012). J. Org. Chem. 77, 7693-7699.]); Heydri & Tahamipour (2011[Heydri, R. & Tahamipour, B. (2011). Chem. Lett. 22, 1281-1284.]); Xu & Wang (2011[Xu, Z. & Wang, H. (2011). Synlett, pp. 2907-2912.]); Li et al. (2010[Li, P., Zhao, J., Li, F., Chan, A. S. C. & Kwong, F. Y. (2010). Org. Lett. 12, 5616-5619.], 2011[Li, P., Chan, S. H., Chan, A. S. C. & Kwong, F. Y. (2011). Adv. Synth. Catal. 353, 1179-1184.]); Gallier et al. (2009[Gallier, F., Hussain, H., Martel, A., Dujardin, G. & Kirschning, A. (2009). Org. Lett. 11, 3060-3063.]); Besavaiah et al. (2004[Besavaiah, D., Sharada, D. S. & Veerendhar, A. (2004). Tetrahedron Lett. 45, 3081-3083.]). For the structures of related compounds, see: Rappoport & Gazit (1986[Rappoport, Z. & Gazit, A. (1986). J. Org. Chem. 51, 4107-4111.])

[Scheme 1]

Experimental

Crystal data
  • C13H14O4

  • Mr = 234.24

  • Monoclinic, P 21 /c

  • a = 14.0516 (6) Å

  • b = 7.7446 (3) Å

  • c = 12.5113 (5) Å

  • [beta] = 113.727 (1)°

  • V = 1246.44 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 273 K

  • 0.55 × 0.36 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.985

  • 7125 measured reflections

  • 2316 independent reflections

  • 1850 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.136

  • S = 1.08

  • 2316 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13C...O1i 0.96 2.49 3.442 (3) 170
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5063 ).


Acknowledgements

This project was supported by the King Saud University, Deanship of Scientific Research, College of Science Research Center.

References

Besavaiah, D., Sharada, D. S. & Veerendhar, A. (2004). Tetrahedron Lett. 45, 3081-3083.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gallier, F., Hussain, H., Martel, A., Dujardin, G. & Kirschning, A. (2009). Org. Lett. 11, 3060-3063.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Heydri, R. & Tahamipour, B. (2011). Chem. Lett. 22, 1281-1284.
Li, P., Chan, S. H., Chan, A. S. C. & Kwong, F. Y. (2011). Adv. Synth. Catal. 353, 1179-1184.  [CSD] [CrossRef] [ChemPort]
Li, P., Zhao, J., Li, F., Chan, A. S. C. & Kwong, F. Y. (2010). Org. Lett. 12, 5616-5619.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Liu, L., Sarkisian, R., Xu, Z. & Wang, H. (2012). J. Org. Chem. 77, 7693-7699.  [CrossRef] [ChemPort] [PubMed]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Rappoport, Z. & Gazit, A. (1986). J. Org. Chem. 51, 4107-4111.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Xu, Z. & Wang, H. (2011). Synlett, pp. 2907-2912.  [ISI] [CrossRef]


Acta Cryst (2013). E69, o919  [ doi:10.1107/S1600536813012464 ]

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