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Volume 68 
Part 1 
Page o179  
January 2012  

Received 21 November 2011
Accepted 8 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 15.9
Details
Open access

5-(3,4-Dimethoxybenzylidene)-1,3-dimethyl-1,3-diazinane-2,4,6-trione

aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: muller.theunis@gmail.com

In the title compound, C15H16N2O5, the dihedral angle between 1,3-diazinane and benzene rings is only 4.27 (1)°. The essentially planar molecular structure is characterized by a short intramolecular C-H...O separation and by an exceptionally large bond angle of 138.25 (14)° at the bridging methine C atom. The methoxy groups deviate somewhat from the plane of the benzene ring, with C-C-O-C torsion angles of -15.6 (1) and 9.17 (6)°. In the crystal, molecules form centrosymmetric dimers via donor-acceptor [pi]-[pi] interactions, with a centroid-centroid distance of 3.401 (1) Å.

Related literature

For the biological activity of 1,3-diazinane derivatives, see: Negwar (2001[Negwar, M. (2001). Organic-Chemical Drugs and their Synonyms, 7th Rev. and Engl. ed., Vol. 4, pp. 2873-2957. Berlin: Akademie.]); Tanaka et al. (1986[Tanaka, K., Chen, X., Kimura, T. & Yoneda, F. (1986). Chem. Pharm. Bull. 34, 3945-3948.], 1988[Tanaka, K., Chen, X., Kimura, T. & Yoneda, F. (1988). Chem. Pharm. Bull. 36, 66-69.]). For the use of pyridine-type ligands in catalysis models, see: Roodt et al. (2011[Roodt, A., Visser, H. G. & Brink, A. (2011). Crystallogr. Rev. 66, 241-280.]); van der Westhuizen et al. (2010[Westhuizen, H. J. van der, Meijboom, R., Schutte, M. & Roodt, A. (2010). Inorg. Chem. 49, 9599-9608.]). For related structures, see: Panchatcharam et al. (2009[Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2394.]); Rezende et al. (2005[Rezende, M. C., Dominguez, M., Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o306-o311.]). For the synthesis, see: Prajapati et al. (2006[Prajapati, D. & Gohain, M. (2006). Beilstein J. Org. Chem. 2, No. 11, doi:10.1186/1860-5397-2-11.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16N2O5

  • Mr = 304.3

  • Triclinic, [P \overline 1]

  • a = 7.3086 (2) Å

  • b = 8.4033 (3) Å

  • c = 11.8705 (5) Å

  • [alpha] = 82.5685 (18)°

  • [beta] = 77.6686 (17)°

  • [gamma] = 71.1469 (15)°

  • V = 672.58 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.15 × 0.12 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.994

  • 12172 measured reflections

  • 3233 independent reflections

  • 2478 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.05

  • 3233 reflections

  • 203 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O3 0.93 2.08 2.871 (2) 142

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: DIAMOND (Brandenberg & Putz, 2005[Brandenberg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2039 ).


Acknowledgements

The University of the Free State and Sasol Ltd are gratefully acknowledged, for financial support, and Johannes van Tonder for the NMR data and help with the synthesis of the title compound. Special thanks are due to Professor Andreas Roodt.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brandenberg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Negwar, M. (2001). Organic-Chemical Drugs and their Synonyms, 7th Rev. and Engl. ed., Vol. 4, pp. 2873-2957. Berlin: Akademie.
Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2394.  [CSD] [CrossRef] [details]
Prajapati, D. & Gohain, M. (2006). Beilstein J. Org. Chem. 2, No. 11, doi:10.1186/1860-5397-2-11.
Rezende, M. C., Dominguez, M., Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o306-o311.  [CSD] [CrossRef] [details]
Roodt, A., Visser, H. G. & Brink, A. (2011). Crystallogr. Rev. 66, 241-280.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tanaka, K., Chen, X., Kimura, T. & Yoneda, F. (1986). Chem. Pharm. Bull. 34, 3945-3948.  [CrossRef] [ChemPort]
Tanaka, K., Chen, X., Kimura, T. & Yoneda, F. (1988). Chem. Pharm. Bull. 36, 66-69.
Westhuizen, H. J. van der, Meijboom, R., Schutte, M. & Roodt, A. (2010). Inorg. Chem. 49, 9599-9608.  [ISI] [PubMed]


Acta Cryst (2012). E68, o179  [ doi:10.1107/S1600536811052986 ]

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