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Volume 69 
Part 1 
Page o49  
January 2013  

Received 2 December 2012
Accepted 4 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 15.7
Details
Open access

1,3-Diethyl-2-sulfanylidene-5-(2,4,5-trimethoxybenzylidene)-1,3-diazinane-4,6-dione

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
Correspondence e-mail: aasiri2@kau.edu.sa, rehman_pcsir@yahoo.com

The title compound, C18H22N2O5S, is largely planar, with an r.m.s. deviation of 0.0546 (1) Å of atoms from the mean plane through all non-H atoms except for the methyl groups. The benzene and pyrimidinedione rings are inclined to one another at a dihedral angle of 1.41 (7)°. In the crystal, weak C-H...O interactions connect the molecules into chains propagating along the b-axis direction.

Related literature

For the synthesis of the title compound, see: Asiri et al. (2004[Asiri, A. M., Alamry, K. A., Jalboutb, A. F. & Zhang, S. (2004). Molbank, 2004, m359.]). For a related structure, see: Asiri et al. (2009[Asiri, A. M., Khan, S. A. & Ng, S. W. (2009). Acta Cryst. E65, o1820.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N2O5S

  • Mr = 378.44

  • Monoclinic, P 21 /c

  • a = 7.9711 (1) Å

  • b = 17.4106 (3) Å

  • c = 13.5265 (2) Å

  • [beta] = 99.237 (2)°

  • V = 1852.89 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.83 mm-1

  • T = 296 K

  • 0.29 × 0.10 × 0.09 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.875, Tmax = 1.000

  • 14850 measured reflections

  • 3777 independent reflections

  • 3083 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.121

  • S = 1.05

  • 3777 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13C...O2i 0.96 2.58 3.455 (2) 152
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5286 ).


Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via the Research Group Track (grant No. 3-102/428).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Asiri, A. M., Alamry, K. A., Jalboutb, A. F. & Zhang, S. (2004). Molbank, 2004, m359.
Asiri, A. M., Khan, S. A. & Ng, S. W. (2009). Acta Cryst. E65, o1820.  [CSD] [CrossRef] [details]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o49  [ doi:10.1107/S1600536812049707 ]

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