Methyl 2,6-bis­[(5-chloro-4,6-dimeth­oxy­pyrimidin-2-yl)­oxy]benzoate

Fun, H.-K.; Goh, J.H.; Rai, S.; Isloor, A.M.; Shetty, P.

doi:10.1107/S1600536810024785

Volume 66
Part 7
Pages o1869-o1870
July 2010

Received 23 June 2010
Accepted 24 June 2010
Online 30 June 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.129
Data-to-parameter ratio = 25.8
Details

Methyl 2,6-bis[(5-chloro-4,6-dimethoxypyrimidin-2-yl)oxy]benzoate

Hoong-Kun Fun,^a ^*⁺ Jia Hao Goh,^a ⁺⁺ Sankappa Rai,^b Arun M. Isloor ^c and Prakash Shetty ^d

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India,^cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^dDepartment of Printing, Manipal Institute of Technology, Manipal University, Manipal 576 104, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₀H₁₈Cl₂N₄O₈, the two pyrimidine rings are inclined at dihedral angles of 66.68 (5) and 71.91 (6)° with respect to the central benzene ring. In the crystal structure, intermolecular C-HN hydrogen bonds link neighbouring molecules into a ribbon-like structure along the b axis. The ribbons are interconnected into a two-dimensional network parallel to the bc plane by short intermolecular ClCl [3.4427 (6) Å] and ClO [3.1420 (9) and 3.1750 (11) Å] interactions. The crystal structure is further stabilized by intermolecular [pi] - [pi] interactions [centroid-centroid distance 3.4552 (8) Å] involving the pyrimidine rings.

Related literature

For general background to and applications of the title compound, see: Koichiro et al. (1988, 1998); He et al. (2007); Li et al. (2006); Gerorge (1983). For graph-set descriptions of hydrogen-bonded ring motifs, see: Bernstein et al. (1995). For a closely related structure, see: Li & Luo (2006). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₀H₁₈Cl₂N₄O₈
M_r = 513.28
Monoclinic, C 2/c
a = 29.354 (3) Å
b = 8.0485 (8) Å
c = 22.5923 (19) Å
= 123.014 (2)°
V = 4475.7 (7) Å³
Z = 8
Mo K radiation
= 0.35 mm^-1
T = 100 K
0.58 × 0.31 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.825, T_max = 0.948
22170 measured reflections
8040 independent reflections
6824 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.129
S = 1.08
8040 reflections
312 parameters
H-atom parameters constrained
_max = 0.71 e Å^-3
_min = -0.55 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16AN1ⁱ	0.96	2.58	3.5018 (19)	161
C20-H20AN3ⁱⁱ	0.96	2.59	3.5148 (19)	161
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5115 ).

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. AMI is thankful to the Head of the Chemistry Department and the Director, National Institute of Technology-Karnataka for their encouragement. AMI also thanks USM for a partially sponsored research visit to the X-ray Crystallography Unit, School of Physics, USM.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Gerorge, L. (1983). US Patent No. 4 394 506.
He, Y.-Z., Li, Y.-X., Zhu, X.-L., Xi, Z., Niu, C., Wan, J., Zhang, L. & Yang, G.-F. (2007). J. Chem. Inf. Model. 47, 2335-2344.
Koichiro, S., Shoji, K., Yasubumi, T., Takeshige, M. & Ryo, Y. (1988). Jpn Patent No. JP 88 132 167; Chem. Abstr. (1998), 112, 216956.
Koichiro, S., Shoji, K., Yasubumi, T., Takeshige, M. & Ryo, Y. (1998). Chem. Abstr. 112, 216956.
Li, Y.-X. & Luo, Y.-P. (2006). Acta Cryst. E62, o1323-o1325.
Li, Y.-X., Luo, Y.-P., Xi, Z., Niu, C., He, Y.-Z. & Yang, G.-F. (2006). J. Agric. Food Chem. 54, 9135-9139.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds