4-[(4-Amino-3-pyrid­yl)imino­meth­yl]benzonitrile

Fun, H.-K.; Kargar, H.; Kia, R.

doi:10.1107/S1600536808037070

Volume 64
Part 12
Page o2342
December 2008

Received 7 November 2008
Accepted 10 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.074
wR = 0.219
Data-to-parameter ratio = 11.8
Details

4-[(4-Amino-3-pyridyl)iminomethyl]benzonitrile

Hoong-Kun Fun,^a ^* Hadi Kargar ^b ⁺ and Reza Kia ^a

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the potential mono-Schiff base ligand title compound, C₁₃H₁₀N₄, contains two crystallographically independent molecules, A and B. In molecule A, the two rings are twisted from each other by 13.90 (18)°. By contrast, the dihedral angle between the two rings in molecule B is 0.67 (19)°. In the crystal structure, molecules are linked through intermolecular N-HN interactions via R₄⁴(32) motifs, forming two-dimensional arrays. The short distances between the centroids of the six-membered rings indicate the existence of [pi] - [pi] interactions [centroid-centroid distances = 3.6880 (17)-3.7466 (15) Å].

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Li et al. (2005); Bomfim et al. (2005); Glidewell et al. (2005, 2006); Sun et al. (2004); Fun et al. (2008).

Experimental

Crystal data

C₁₃H₁₀N₄
M_r = 222.25
Monoclinic, P 2₁ /c
a = 13.5560 (8) Å
b = 12.3000 (7) Å
c = 15.7514 (8) Å
= 124.651 (2)°
V = 2160.5 (2) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 100.0 (1) K
0.45 × 0.09 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.962, T_max = 0.994
18251 measured reflections
3810 independent reflections
2372 reflections with I > 2(I)
R_int = 0.060

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.219
S = 1.03
3810 reflections
323 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.63 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3A-H2NAN4Aⁱ	0.92 (4)	2.26 (4)	3.155 (4)	165 (3)
N3A-H1NAN1Bⁱⁱ	0.89 (4)	2.33 (5)	3.080 (4)	143 (4)
N3B-H2NBN1Aⁱⁱⁱ	0.89 (4)	2.42 (4)	3.112 (4)	136 (4)
N3B-H1NBN4Bⁱ	0.90 (4)	2.36 (4)	3.220 (4)	159 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2327 ).

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bomfim, J. A. S., Wardell, J. L., Low, J. N., Skakle, J. M. S. & Glidewell, C. (2005). Acta Cryst. C61, o53-o56.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308.
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. E61, o3551-o3553.
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2006). Acta Cryst. C62, o1-o4.
Li, Y.-G., Zhu, H.-L., Chen, X.-Z. & Song, Y. (2005). Acta Cryst. E61, o4156-o4157.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Sun, Y.-X., You, Z.-L. & Zhu, H.-L. (2004). Acta Cryst. E60, o1707-o1708.

organic compounds