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

Asiri, A.M.; Arshad, M.N.; Zia-ur-Rehman, M.; Sobahi, T.R.

doi:10.1107/S1600536812049707

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 15.7
Details

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

Abdullah M. Asiri,^a,^b ^* Muhammad Nadeem Arshad,^a,^b Muhammad Zia-ur-Rehman ^c ^* and Tariq R. Sobahi ^a

^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-HO 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). For a related structure, see: Asiri et al. (2009).

Experimental

Crystal data

C₁₈H₂₂N₂O₅S
M_r = 378.44
Monoclinic, P 2₁ /c
a = 7.9711 (1) Å
b = 17.4106 (3) Å
c = 13.5265 (2) Å
= 99.237 (2)°
V = 1852.89 (5) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.875, T_max = 1.000
14850 measured reflections
3777 independent reflections
3083 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.121
S = 1.05
3777 reflections
240 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13CO2ⁱ	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); 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: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

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.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds