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

Hoong-Kun Fun; Hadi Kargar; Reza Kia

doi:10.1107/S1600536808037070

. 2008 Nov 13;64(Pt 12):o2342. doi: 10.1107/S1600536808037070

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

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

PMCID: PMC2959807 PMID: 21581317

Abstract

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—H⋯N interactions via R₄⁴(32) motifs, forming two-dimensional arrays. The short distances between the centroids of the six-membered rings indicate the existence of π–π 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,
a = 13.5560 (8) Å
b = 12.3000 (7) Å
c = 15.7514 (8) Å
β = 124.651 (2)°
V = 2160.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.219
S = 1.03
3810 reflections
323 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037070/tk2327sup1.cif

e-64-o2342-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037070/tk2327Isup2.hkl

e-64-o2342-Isup2.hkl^{(186.8KB, 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
N3A—H2NA⋯N4Aⁱ	0.92 (4)	2.26 (4)	3.155 (4)	165 (3)
N3A—H1NA⋯N1Bⁱⁱ	0.89 (4)	2.33 (5)	3.080 (4)	143 (4)
N3B—H2NB⋯N1Aⁱⁱⁱ	0.89 (4)	2.42 (4)	3.112 (4)	136 (4)
N3B—H1NB⋯N4Bⁱ	0.90 (4)	2.36 (4)	3.220 (4)	159 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry and play an important role in the development of coordination chemistry (Fun et al., 2008). Structures of Schiff bases derived from substituted benzaldehydes have been reported previously (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004; Fun et al., 2008).

Each imino (C ═N) functional group is co-planar with the adjacent benzene ring in (I), Fig. 1. Two independent molecules, A and B, comprise the crystallographic asymmetric unit. In molecule A, the two phenyl rings are twisted from each other by 13.90 (18)°. The dihedral angle between the two phenyl rings in molecule B is 0.67 (19)° which indicates the molecule is planar. In the crystal structure, molecules are linked together through intermolecular N—H···N interactions via R₄⁴(32) motifs to form 2-D arrays parallel to the ab-plane, Fig. 2 & Table 1. The short distances between the centroids of the six-membered rings prove the existence of π–π interactions [Cg1···Cg4ⁱ = 3.7466 (15) Å, (i) x, 1/2 - y, -1/2 + z; Cg2···Cg3ⁱ = 3.6894 (14) Å; Cg3···Cg4ⁱⁱ, (ii) 1 - x,-y, 1 - z; Cg1, Cg2, Cg3, and Cg4 are the centroids of the N1A/C1A–C5A, C7A–C12A, N1B/C1B–C5B, and C7B–C12B rings, respectively.

Experimental

The synthetic method has been described earlier (Fun et al., 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution of (I) held at room temperature.