4-[(E)-Phenyl­imino­meth­yl]benzonitrile

Mmuhammad Akram Kashmiri; M Nawaz Tahir; Muhammad Akhtar; Mushtaq Ahmed; Asif Hanif Ch

doi:10.1107/S1600536808008672

. 2008 Apr 2;64(Pt 5):o790. doi: 10.1107/S1600536808008672

4-[(E)-Phenyliminomethyl]benzonitrile

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

PMCID: PMC2961095 PMID: 21202283

Abstract

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—H⋯N hydrogen bonds link the molecules into centrosymmetric R ₂ ²(10) dimers. A weak π–π 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⋯π 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,
a = 7.2673 (4) Å
b = 10.0287 (7) Å
c = 15.4306 (12) Å
β = 96.177 (2)°
V = 1118.08 (13) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.118
S = 1.03
2883 reflections
176 parameters
All H-atom parameters refined
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.10 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008672/hk2445sup1.cif

e-64-0o790-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008672/hk2445Isup2.hkl

e-64-0o790-Isup2.hkl^{(138.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2ⁱ	0.980 (13)	2.616 (14)	3.473 (2)	146.1 (10)
C5—H5⋯Cgⁱⁱ	0.975 (13)	2.650 (14)	3.5970 (17)	163.9 (11)

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Symmetry codes: (i) Inline graphic ; (ii) . Cg is the centroid of atoms C9–C14.

Acknowledgments

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

supplementary crystallographic information

Comment

The crystal structures of p-halo-N-(p-cyanobenzylidene)- aniline and p-cyano-N-(p-halobenzylidene)aniline, (halo = bromo and chloro) (Ojala et al., 2002) have been reported, previously. The title compound, (I), differs due to no attachment of halogen atoms. It is prepared in aqueous medium and we report herein its crystal structure.

The molecule of (I), (Fig. 1), is a Schiff base ligand of aniline and p-cyanobenzaldehyde. The bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar, and they are oriented at a dihedral angle of 32.22 (6)°.

In the crystal structure, intermolecular C-H···N hydrogen bonds (Table 1) link the molecules into centrosymmetric R₂²(10) dimers (Fig. 2) (Bernstein et al., 1995; Etter, 1990), in which they may be effective in the stabilization of the structure. A weak π···π interaction between the A rings, at x, y, z and 1 - x, 1 - y, -z, further stabilizes the structure, with a centroid-centroid distance of 3.8447 (3) Å. There is also a C—H···π interaction between the ring B at x - 1/2, 1/2 -y, z - 1/2 and C5-H5, with H5-centroid distance of 2.650 (14) Å.

Experimental

The starting materials employed were first purified by distillation or crystallization just before use. The experiment was performed in stoppered flask at room temperature. The title compound was synthesized by using equimolecular mixture of aniline (5 mmol) and p-cyanobenzaldehyde (5 mmol) of pH = 9 in aqueous medium. The product was precipitated after a few minutes, and separated by filtration, washed with a small amount of water and dried for 2 d at room temperature in a vacuum desicator. The dried filtrate was used for X-ray analysis (yield; 53.09%, m.p. 339 K).