2-[3-Meth­oxy-5-(pyrimidin-2-yl)phen­yl]pyrimidine

Hu, J.; Wu, Y.; Zhang, D.; Li, X.; Jin, W.

doi:10.1107/S1600536813002663

Volume 69
Part 3
Page o333
March 2013

Received 17 January 2013
Accepted 27 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 13.5
Details

2-[3-Methoxy-5-(pyrimidin-2-yl)phenyl]pyrimidine

Jiena Hu,^a Yang Wu,^a ^* Dengqing Zhang,^a ^* Xianying Li ^b and Wusong Jin ^a

^aCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China, and ^bSchool of Environmental Science and Engineering, Donghua University, 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China
Correspondence e-mail: wsjin@dhu.edu.cn, dqzhang@dhu.edu.cn

The title compound, C₁₅H₁₂N₄O, was synthesized by a standard Suzuki cross-coupling reaction. The terminal pyrimidine rings are rotated at dihedral angles of 12.06 (4) and -13.13 (4)° with respect to the central benzene ring. In the crystal, the molecules are connected by two kinds of C-HN hydrogen bonds, forming zigzag chains along the c axis. Weak [pi] - [pi] interactions between the benzene and one of the pyrimidine rings are also found and stack the molecules along the b axis [centroid-centroid distance = 4.112 (3) Å].

Related literature

For general background to the chemistry of tridentate NCN ligands, see: Pugh & Danopoulos (2007); Wu et al. (2009, 2012); Williams (2009); Wang et al. (2010). For the synthesis of the title compound, see: Avitia et al. (2011); Wakioka et al. (2010); Cardenas & Echavarren (1999).

Experimental

Crystal data

C₁₅H₁₂N₄O
M_r = 264.29
Orthorhombic, P b c a
a = 11.3779 (8) Å
b = 8.0954 (6) Å
c = 27.3371 (18) Å
V = 2518.0 (3) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.28 × 0.21 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.800, T_max = 1.000
14088 measured reflections
2461 independent reflections
2059 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.123
S = 1.04
2461 reflections
182 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9N4ⁱ	0.93	2.69	3.597 (2)	166
C15-H15BN3ⁱⁱ	0.96	2.69	3.547 (2)	149
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SJ5297 ).

Acknowledgements

This work was supported by STCSM (12JC1400200).

References

Avitia, B., MacIntosh, E., Muhia, S. & Kelson, E. (2011). Tetrahedron Lett. 52, 1631-1634.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cardenas, D. J. & Echavarren, A. M. (1999). Organometallics, 18, 3337-3341.
Pugh, D. & Danopoulos, A. A. (2007). Coord. Chem. Rev. 251, 610-641.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wakioka, M., Ikegami, M. & Ozawa, F. (2010). Macromolecules, 43, 6980-6985.
Wang, Z., Turner, E., Mahoney, V., Madakuni, S., Groy, T. & Li, A. (2010). Inorg. Chem. 49, 11276-11286.
Williams, J. A. G. (2009). Chem. Soc. Rev. 38, 1783-1801.
Wu, L. Y., Hao, X. Q., Xu, Y. X., Jia, M. Q., Wang, Y. N., Gong, J. F. & Song, M. P. (2009). Organometallics, 28, 3369-3380.
Wu, Y., Xie, D., Zhang, D., Li, X. & Jin, W. (2012). Acta Cryst. E68, m1210-m1211.

organic compounds