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Volume 69 
Part 1 
Page o50  
January 2013  

Received 28 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 12.4
Details
Open access

2,2-Dimethyl-5-(2-nitrobenzylidene)-1,3-dioxane-4,6-dione

aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico, and bDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, AP 24, 86690, Cuanduacán Tab., Mexico
Correspondence e-mail: angel.mendoza.m@gmail.com

The asymmetric unit of the title compound, C13H11NO6, contains two molecules in both of which the six-membered 1,3-dioxane-4,6-dione ring shows a screw-boat conformation. The dihedral angles between the best planes through the six-membered rings are 47.8 (2) and 49.8 (2)°. In the crystal, C-H...O interactions link the molecules, building a supramolecular sheet parallel to the c axis.

Related literature

For general applications of Meldrum's acid, see: Palasz et al. (2007[Palasz, A., Jelska, K., Ozóg, M. & Serda, P. (2007). Monatsh. Chem. 138, 481-488.]); Fillion et al. (2006[Fillion, E., Dumas, A. & Hogg, S. A. (2006). J. Org. Chem. 71, 9899-9902.]); Mizukami et al. (1993[Mizukami, S., Kihara, N. & Endo, T. (1993). Tetrahedron Lett. 34, 7437-7440.]). For the synthesis of heterocyclic compounds, see: Scott & Raston (2000[Scott, J. L. & Raston, C. L. (2000). Green Chem. 2, 245-247.]); Alvim et al. (2005[Alvim, J. Jr, Días, R. L. A., Castilhob, M. S., Olivab, G. & y Corréa, A. G. (2005). J. Braz. Chem. Soc. 16, 763-773.]); Fillion & Dumas (2008[Fillion, E. & Dumas, A.-M. (2008). J. Org. Chem. 73, 2920-2923.]). For combinatorial synthesis, see: Shaabani et al. (2004[Shaabani, A., Teimouri, M. B. & Bijanzadeh, H. R. (2004). Russ. J. Org. Chem. 40, 976-981.]); Wang et al. (2007[Wang, X.-S., Zhang, M.-M., Jiang, H., Yaoa, C.-S. & Tua, S.-J. (2007). Tetrahedron, 63, 4439-4449.]); Cochard et al. (2004[Cochard, F., Laronze, M., Sigaut, P., SAPI, J. & Laronze, J.-Y. (2004). Tetrahedron Lett. 45, 1703-1707.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For NMR data, see: Bigi et al. (2001[Bigi, F., Carloni, S., Ferrari, L., Maggi, R., Mazzacani, A. & Sartori, G. (2001). Tetrahedron Lett. 42, 5203-5205.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11NO6

  • Mr = 277.23

  • Triclinic, [P \overline 1]

  • a = 10.0240 (4) Å

  • b = 10.4830 (5) Å

  • c = 12.4076 (5) Å

  • [alpha] = 105.385 (4)°

  • [beta] = 94.669 (3)°

  • [gamma] = 93.096 (3)°

  • V = 1249.03 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 130 K

  • 0.39 × 0.22 × 0.14 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.968, Tmax = 0.985

  • 8703 measured reflections

  • 4526 independent reflections

  • 3902 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.03

  • 4526 reflections

  • 365 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H7...O5 0.93 2.43 2.7970 (16) 104
C11-H10...O8 0.93 2.45 3.239 (2) 143
C21-H13...O5i 0.96 2.58 3.4188 (17) 145
C16-H18...O12 0.93 2.54 2.8582 (18) 100
C16-H18...O2ii 0.93 2.55 3.4486 (18) 163
C24-H21...O5iii 0.93 2.48 3.3676 (19) 160
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6875 ).


Acknowledgements

The authors acknowledge the Universidad Juárez Autónoma de Tabasco for financial support via projects UJAT-2009-C05-02 and UJAT-2011-C07-22

References

Alvim, J. Jr, Días, R. L. A., Castilhob, M. S., Olivab, G. & y Corréa, A. G. (2005). J. Braz. Chem. Soc. 16, 763-773.
Bigi, F., Carloni, S., Ferrari, L., Maggi, R., Mazzacani, A. & Sartori, G. (2001). Tetrahedron Lett. 42, 5203-5205.  [ISI] [CrossRef] [ChemPort]
Cochard, F., Laronze, M., Sigaut, P., SAPI, J. & Laronze, J.-Y. (2004). Tetrahedron Lett. 45, 1703-1707.  [ISI] [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fillion, E. & Dumas, A.-M. (2008). J. Org. Chem. 73, 2920-2923.  [CrossRef] [PubMed] [ChemPort]
Fillion, E., Dumas, A. & Hogg, S. A. (2006). J. Org. Chem. 71, 9899-9902.  [CSD] [CrossRef] [PubMed] [ChemPort]
Mizukami, S., Kihara, N. & Endo, T. (1993). Tetrahedron Lett. 34, 7437-7440.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Palasz, A., Jelska, K., Ozóg, M. & Serda, P. (2007). Monatsh. Chem. 138, 481-488.  [ChemPort]
Scott, J. L. & Raston, C. L. (2000). Green Chem. 2, 245-247.  [ISI] [CrossRef] [ChemPort]
Shaabani, A., Teimouri, M. B. & Bijanzadeh, H. R. (2004). Russ. J. Org. Chem. 40, 976-981.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, X.-S., Zhang, M.-M., Jiang, H., Yaoa, C.-S. & Tua, S.-J. (2007). Tetrahedron, 63, 4439-4449.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o50  [ doi:10.1107/S1600536812049677 ]

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