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

García-Álvarez, F.; Romero, N.; Lobato-García, C.E.; Terán, J.L.; Mendoza, A.

doi:10.1107/S1600536812049677

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 12.4
Details

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

Fernando García-Álvarez,^a Nancy Romero,^b Carlos E. Lobato-García,^b Joel L. Terán ^a and Angel Mendoza ^a ^*

^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-HO 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); Fillion et al. (2006); Mizukami et al. (1993). For the synthesis of heterocyclic compounds, see: Scott & Raston (2000); Alvim et al. (2005); Fillion & Dumas (2008). For combinatorial synthesis, see: Shaabani et al. (2004); Wang et al. (2007); Cochard et al. (2004). For puckering parameters, see: Cremer & Pople (1975). For NMR data, see: Bigi et al. (2001).

Experimental

Crystal data

C₁₃H₁₁NO₆
M_r = 277.23
Triclinic, $[P \overline 1]$
a = 10.0240 (4) Å
b = 10.4830 (5) Å
c = 12.4076 (5) Å
= 105.385 (4)°
= 94.669 (3)°
= 93.096 (3)°
V = 1249.03 (10) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.968, T_max = 0.985
8703 measured reflections
4526 independent reflections
3902 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.088
S = 1.03
4526 reflections
365 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H7O5	0.93	2.43	2.7970 (16)	104
C11-H10O8	0.93	2.45	3.239 (2)	143
C21-H13O5ⁱ	0.96	2.58	3.4188 (17)	145
C16-H18O12	0.93	2.54	2.8582 (18)	100
C16-H18O2ⁱⁱ	0.93	2.55	3.4486 (18)	163
C24-H21O5ⁱⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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

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Wang, X.-S., Zhang, M.-M., Jiang, H., Yaoa, C.-S. & Tua, S.-J. (2007). Tetrahedron, 63, 4439-4449.

organic compounds