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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 [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...N 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[Pugh, D. & Danopoulos, A. A. (2007). Coord. Chem. Rev. 251, 610-641.]); Wu et al. (2009[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.], 2012[Wu, Y., Xie, D., Zhang, D., Li, X. & Jin, W. (2012). Acta Cryst. E68, m1210-m1211.]); Williams (2009[Williams, J. A. G. (2009). Chem. Soc. Rev. 38, 1783-1801.]); Wang et al. (2010[Wang, Z., Turner, E., Mahoney, V., Madakuni, S., Groy, T. & Li, A. (2010). Inorg. Chem. 49, 11276-11286.]). For the synthesis of the title compound, see: Avitia et al. (2011[Avitia, B., MacIntosh, E., Muhia, S. & Kelson, E. (2011). Tetrahedron Lett. 52, 1631-1634.]); Wakioka et al. (2010[Wakioka, M., Ikegami, M. & Ozawa, F. (2010). Macromolecules, 43, 6980-6985.]); Cardenas & Echavarren (1999[Cardenas, D. J. & Echavarren, A. M. (1999). Organometallics, 18, 3337-3341.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N4O

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.800, Tmax = 1.000

  • 14088 measured reflections

  • 2461 independent reflections

  • 2059 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.123

  • S = 1.04

  • 2461 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...N4i 0.93 2.69 3.597 (2) 166
C15-H15B...N3ii 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CrossRef] [ChemPort]
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cardenas, D. J. & Echavarren, A. M. (1999). Organometallics, 18, 3337-3341.  [ChemPort]
Pugh, D. & Danopoulos, A. A. (2007). Coord. Chem. Rev. 251, 610-641.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wakioka, M., Ikegami, M. & Ozawa, F. (2010). Macromolecules, 43, 6980-6985.  [ISI] [CrossRef] [ChemPort]
Wang, Z., Turner, E., Mahoney, V., Madakuni, S., Groy, T. & Li, A. (2010). Inorg. Chem. 49, 11276-11286.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Williams, J. A. G. (2009). Chem. Soc. Rev. 38, 1783-1801.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [CSD] [CrossRef] [ChemPort]
Wu, Y., Xie, D., Zhang, D., Li, X. & Jin, W. (2012). Acta Cryst. E68, m1210-m1211.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o333  [ doi:10.1107/S1600536813002663 ]

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