1,4-Bis(3-pyridylmethyl­eneamino­meth­yl)benzene

He, M.-Y.; Li, C.; Xu, H.; Hu, Z.-J.; Chen, Q.

doi:10.1107/S1600536809000658

Volume 65
Part 2
Page o285
February 2009

Received 1 December 2008
Accepted 7 January 2009
Online 10 January 2009

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.002 Å
R = 0.048
wR = 0.101
Data-to-parameter ratio = 15.2
Details

1,4-Bis(3-pyridylmethyleneaminomethyl)benzene

Ming-Yang He,^a Chao Li,^a Huan Xu,^a Zhao-Jian Hu ^a and Qun Chen ^a ^*

^aKey Laboratory of Fine Petrochemical Technology, Jiangsu Polytechnic University, Changzhou 213164, People's Republic of China
Correspondence e-mail: chenqunjpu@yahoo.com

The title compound, C₂₀H₁₈N₄, is a flexible 3,3'-bipyridyl-type ligand with a long spacer group between the two pyridyl functions. The molecule crystallizes around an inversion center, with one half-molecule in the asymmetric unit and a dihedral angle of 71.85 (8)° between the pyridine ring and the central benzene ring.

Related literature

For background information on bipyridyl-type Schiff base ligands, see: Cho et al. (2006); Haga et al. (1985); Mahmoudi et al. (2007); Wang et al. (2008). Haga et al. (1985) describe the synthesis of the title compound.

Experimental

Crystal data

C₂₀H₁₈N₄
M_r = 314.38
Monoclinic, P 2₁ /c
a = 6.0990 (11) Å
b = 14.589 (3) Å
c = 9.9481 (18) Å
= 107.851 (3)°
V = 842.5 (3) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 291 (2) K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.98, T_max = 0.98
6535 measured reflections
1661 independent reflections
1085 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.101
S = 1.01
1661 reflections
109 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.12 e Å^-3

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

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2166 ).

Acknowledgements

The authors thank the Center for Testing and Analysis at Yangzhou University for support.

References

Bruker (2000). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, B. Y., Min, D. W. & Lee, S. W. (2006). Cryst. Growth Des. 6, 342-347.
Haga, M. & Koizumi, K. (1985). Inorg. Chim. Acta, 104, 47-50.
Mahmoudi, G., Morsali, A., Hunter, A. D. & Zeller, M. (2007). CrystEngComm, 9, 704-714.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Q., Yang, R., Zhuang, C. F., Zhang, J. Y., Kang, B. S. & Su, C. Y. (2008). Eur. J. Inorg. Chem. 10, 1702-1711.

organic compounds