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

Abdullah M Asiri; Muhammad Nadeem Arshad; Muhammad Zia-ur-Rehman; Tariq R Sobahi

doi:10.1107/S1600536812049707

. 2012 Dec 8;69(Pt 1):o49. doi: 10.1107/S1600536812049707

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,^*, Tariq R Sobahi ^a

PMCID: PMC3588229 PMID: 23476432

Abstract

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 ▶). For a related structure, see: Asiri et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₂₂N₂O₅S
M _r = 378.44
Monoclinic,
a = 7.9711 (1) Å
b = 17.4106 (3) Å
c = 13.5265 (2) Å
β = 99.237 (2)°
V = 1852.89 (5) Å³
Z = 4
Cu Kα radiation
μ = 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 > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.121
S = 1.05
3777 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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 Material

Click here for additional data file.^{(26.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049707/sj5286sup1.cif

e-69-00o49-sup1.cif^{(26.2KB, cif)}

Click here for additional data file.^{(185.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049707/sj5286Isup2.hkl

e-69-00o49-Isup2.hkl^{(185.2KB, hkl)}

Click here for additional data file.^{(7.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812049707/sj5286Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

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).

supplementary crystallographic information

Comment

The title compound is related to the arylidene 5-[3-(2,5-dimethoxyphenyl)prop- 2-enylidene]-1,3-diethyl-2-thioxohexahydropyrimidine-4,6-dione (II) already reported by our group (Asiri et al., 2009). The molecule is largely planar with a dihedral angle between the benzene and pyrimidine dione rings of 1.41 (7)°. The r. m. s. deviation of atoms from the best fit plane through the non-hydrogen atoms C1/N1/C2/C3/C4/N2/S1/O1/O2/C5/C6/C7/C8/C9/C10/C11/C12/ C14/O3/O4/O5) is 0.0546 (1) Å. Atoms S1 and O1 are displaced from this plane by -0.1187 (1) Å and 0.1131 (2) Å respectively. Non-classical C13–H13C···O2 hydrogen bonds connect the molecule into chains along the b axis (Table. 1, Fig. 2).

Experimental

1,3-Diethyl-2-thiobarbituric acid (0.005 mol) and 2,4,5-trimethoxybenzaldehyde (0.005 mol) were heated in ethanol (15 ml) for 3 h; several drops of diethylamine were added. The progress of reaction was monitored by TLC. The mixture was cooled and the resulting solid was recrystallized from methanol (Asiri et al. 2004) by slow evaporation at room temperature.