Received 17 January 2013
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: firstname.lastname@example.org, email@example.com
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 - 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].
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).
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 ).
This work was supported by STCSM (12JC1400200).
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.