N-(2-Pyridylmethanimidamido)pyridine-2-carboximidamide

Wang, Y.

doi:10.1107/S1600536810016351

Volume 66
Part 6
Page o1515
June 2010

Received 2 April 2010
Accepted 4 May 2010
Online 29 May 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.073
wR = 0.222
Data-to-parameter ratio = 17.0
Details

N-(2-Pyridylmethanimidamido)pyridine-2-carboximidamide

Yingchun Wang ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: wyingchun0107@126.com

In the title molecule, C₁₂H₁₂N₆, the dihedral angles between the pyridine rings and the central dimethanimine-hydrazine group are 0.30 (3) and 13.94 (3)°. Two intramolecular N-HN hydrogen bonds stabilize the planar conformation of one pyridine ring with respect to its hydrazine-residue neighbour, whereas the other pyridine ring and an N-bonded H atom are rotated out of the plane and link the molecules into intermolecular N-HN chains propagating in [010].

Related literature

For the phase transition of pyridinium tetrachloroiodate(III) studied by X-ray analysis and dielectric and heat capacity measurements, see: Asaji et al. (2007). For the synthesis of 2-pyridylpyridines via Diels-Alder reactions between 3-pyridyl-1,2,4-triazines and vinylalcanoates, see: Shintou et al. (2005). For the ferroelecric properties of pyridinum perrhenate, see: Wasicki et al. (1997).

Experimental

Crystal data

C₁₂H₁₂N₆
M_r = 240.28
Orthorhombic, P b c a
a = 13.218 (3) Å
b = 9.4979 (19) Å
c = 19.811 (4) Å
V = 2487.2 (9) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.5, T_max = 0.5
23997 measured reflections
2848 independent reflections
1934 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.073
wR(F²) = 0.222
S = 1.09
2848 reflections
168 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.46 e Å^-3
_min = -0.67 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4BN5ⁱ	0.86	2.60	3.096 (3)	117
N2-H2BN1	0.79 (4)	2.34 (4)	2.670 (4)	106 (3)
N3-H3BN5	0.86	2.33	2.619 (3)	100
N4-H4BN2	0.86	2.31	2.608 (3)	101
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2254 ).

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Asaji, T., Eda, K., Fujimori, H., Adachi, T., Shibusawa, T. & Oguni, M. (2007). J. Mol. Struct. 826, 24-28.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shintou, T., Ikeuchi, F., Kuwabara, H., Umihara, K. & Itoh, I. J. (2005). Chemistry Lett. 34, 836-838.
Wasicki, J., Czarnecki, P., Pajak, Z., Nawrocik, W. & Szepanski, W. (1997). J. Chem. Phys. 107, 576-578.

organic compounds

N-(2-Pyridylmethanimidamido)pyridine-2-carboximidamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References