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

Gohain, M.; Muller, T.J.; Bezuidenhoudt, B.C.B.

doi:10.1107/S1600536811052986

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 15.9
Details

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

Mukut Gohain,^a Theunis J. Muller ^a ^* and Barend C. B. Bezuidenhoudt ^a

^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-HO 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); Tanaka et al. (1986, 1988). For the use of pyridine-type ligands in catalysis models, see: Roodt et al. (2011); van der Westhuizen et al. (2010). For related structures, see: Panchatcharam et al. (2009); Rezende et al. (2005). For the synthesis, see: Prajapati et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₆N₂O₅
M_r = 304.3
Triclinic, $[P \overline 1]$
a = 7.3086 (2) Å
b = 8.4033 (3) Å
c = 11.8705 (5) Å
= 82.5685 (18)°
= 77.6686 (17)°
= 71.1469 (15)°
V = 672.58 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.984, T_max = 0.994
12172 measured reflections
3233 independent reflections
2478 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.113
S = 1.05
3233 reflections
203 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O3	0.93	2.08	2.871 (2)	142

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
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.
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.
Roodt, A., Visser, H. G. & Brink, A. (2011). Crystallogr. Rev. 66, 241-280.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tanaka, K., Chen, X., Kimura, T. & Yoneda, F. (1986). Chem. Pharm. Bull. 34, 3945-3948.
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.

organic compounds