7-(Benzyl­sulfan­yl)-5-(2-methoxy­phen­yl)-1,3-dimethyl-5,6-dihydro­pyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Bazgir, A.; Faraji, F.

doi:10.1107/S160053680802401X

Volume 64
Part 9
Page o1666
September 2008

Received 19 July 2008
Accepted 29 July 2008
Online 6 August 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.135
Data-to-parameter ratio = 19.4
Details

7-(Benzylsulfanyl)-5-(2-methoxyphenyl)-1,3-dimethyl-5,6-dihydropyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione

Ayoob Bazgir ^a ^* and Fereshteh Faraji ^b

^aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran, and ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University, Karaj Branch, Karaj, Iran
Correspondence e-mail: a_bazgir@yahoo.com

In the molecule of the title compound, C₂₂H₂₂N₄O₃S, the benzene and phenyl rings are oriented at a dihedral angle of 88.72 (4)°. The other two rings have flattened-boat conformations. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules.

Related literature

For general background, see: Sharma et al. (2004); Quiroga et al. (2002); Devi et al. (2003). For bond-length data, see: Allen et al. (1987). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₂H₂₂N₄O₃S
M_r = 422.51
Monoclinic, P 2₁ /n
a = 10.9216 (9) Å
b = 8.8528 (5) Å
c = 20.7263 (15) Å
= 90.638 (6)°
V = 2003.8 (2) Å³
Z = 4
Mo K radiation
= 0.20 mm^-1
T = 294 (2) K
0.4 × 0.3 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.928, T_max = 0.985
23191 measured reflections
5394 independent reflections
4510 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.135
S = 1.15
5394 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4BO1ⁱ	0.85 (3)	2.02 (3)	2.836 (2)	161 (2)
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); 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: HK2501 ).

Acknowledgements

AB is grateful to the Islamic Azad University, Dorood Branch, for financial support.

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.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Devi, I., Kumar, B. S. D. & Bhuyan, P. J. (2003). Tetrahedron Lett. 44, 8307-8310.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Quiroga, J., Insuasty, H., Insuasty, B., Abonia, R., Cobo, J., Sanchez, A. & Nogueras, M. (2002). Tetrahedron, 58, 4873-4877.
Sharma, P., Rane, N. & Gurram, V. K. (2004). Bioorg. Med. Chem. Lett. 14, 4185-4190.
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds