4-[(E)-Phenyl­imino­meth­yl]benzonitrile

Kashmiri, M.A.; Tahir, M.N.; Akhtar, M.; Ahmed, M.; Hanif Ch, A.

doi:10.1107/S1600536808008672

Volume 64
Part 5
Page o790
May 2008

Received 29 March 2008
Accepted 31 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.119
Data-to-parameter ratio = 16.4
Details

4-[(E)-Phenyliminomethyl]benzonitrile

Mmuhammad Akram Kashmiri,^a M. Nawaz Tahir,^b ^* Muhammad Akhtar,^a Mushtaq Ahmed ^a and Asif Hanif Ch ^a

^aGovernment College University, Department of Chemistry, Lahore, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the molecule of the title compound, C₁₄H₁₀N₂, the two aromatic rings are oriented at a dihedral angle of 32.22 (6)°. In the crystal structure, intermolecular C-HN hydrogen bonds link the molecules into centrosymmetric R₂²(10) dimers. A weak [pi] - [pi] interaction between the cyanobenzene rings, with a centroid-centroid distance of 3.8447 (3) Å, further stabilizes the crystal structure. There is also a C-H [pi] interaction between the aniline ring and a CH group of the cyanobenzene ring.

Related literature

For related structures, see: Ojala et al. (2002). For ring motif details, see: Bernstein et al. (1995); Etter (1990). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₀N₂
M_r = 206.24
Monoclinic, P 2₁ /n
a = 7.2673 (4) Å
b = 10.0287 (7) Å
c = 15.4306 (12) Å
= 96.177 (2)°
V = 1118.08 (13) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 296 (2) K
0.20 × 0.15 × 0.12 mm

Data collection

Bruker Kappa-APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.983, T_max = 0.994
13128 measured reflections
2883 independent reflections
1423 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.118
S = 1.03
2883 reflections
176 parameters
All H-atom parameters refined
_max = 0.13 e Å^-3
_min = -0.10 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N2ⁱ	0.980 (13)	2.616 (14)	3.473 (2)	146.1 (10)
C5-H5Cgⁱⁱ	0.975 (13)	2.650 (14)	3.5970 (17)	163.9 (11)
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of atoms C9-C14.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2445 ).

Acknowledgements

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsion, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsion, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Ojala, C. R., Ojala, W. H., Gleason, W. B. & Britton, D. (2002). J. Chem. Crystallogr. 31, 377-386.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds