1,3-Bis(4-methyl­benz­yl)pyrimidine-2,4(1H,3H)-dione

Li, G.-C.; Song, X.-P.; Zhang, L.-K.; Cui, J.-J.; Yang, F.-L.

doi:10.1107/S1600536809053586

Volume 66
Part 1
Page o193
January 2010

Received 1 December 2009
Accepted 12 December 2009
Online 19 December 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.088
wR = 0.161
Data-to-parameter ratio = 13.7
Details

1,3-Bis(4-methylbenzyl)pyrimidine-2,4(1H,3H)-dione

Gong-Chun Li,^a Xiao-Ping Song,^a Li-Ke Zhang,^a Jiao-Jiao Cui ^a and Feng-Ling Yang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China
Correspondence e-mail: actaeli@gmail.com

In the title molecule, C₂₀H₂₀N₂O₂, the central pyrimidine ring forms dihedral angles of 71.9 (1) and 69.8 (1)° with the two benzene rings. In the crystal, weak intermolecular C-HO hydrogen bonds link molecules into centrosymmetric dimers. The crystal packing exhibits also [pi] - [pi] interactions as indicated by short distances of 3.674 (2) Å between the centroids of the pyrimidine rings of neighbouring molecules.

Related literature

For the crystal structure of 1,3-bis(4-chlorobenzyl)pyrimidine-2,4(1H,3H)-dione, see: Yang & Li (2006).

Experimental

Crystal data

C₂₀H₂₀N₂O₂
M_r = 320.38
Triclinic, $[P \overline 1]$
a = 9.4182 (19) Å
b = 10.102 (2) Å
c = 10.448 (2) Å
= 66.25 (3)°
= 80.79 (3)°
= 71.18 (3)°
V = 860.7 (3) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006) T_min = 0.984, T_max = 0.984
8622 measured reflections
3001 independent reflections
2529 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.088
wR(F²) = 0.161
S = 1.27
3001 reflections
219 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H14O2ⁱ	0.93	2.50	3.430 (4)	174
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2673 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

References

Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, F.-L. & Li, G.-C. (2006). Acta Cryst. E62, o3405-o3406.

organic compounds