4-(1H-Benzimidazol-2-yl)benzonitrile

Wei Dai; Wen-Xiang Wang; Yu-Yuan Zhao; Hong Zhao

doi:10.1107/S1600536808012932

. 2008 May 7;64(Pt 6):o1017. doi: 10.1107/S1600536808012932

4-(1H-Benzimidazol-2-yl)benzonitrile

Wei Dai ^a, Wen-Xiang Wang ^a, Yu-Yuan Zhao ^a, Hong Zhao ^a,^*

PMCID: PMC2961444 PMID: 21202542

Abstract

The molecule of the title compound, C₁₄H₉N₃, is essentially planar, the dihedral angle formed by the benzimidazole ring system with the benzene ring being 3.87 (3)°. In the crystal packing, molecules are linked into zigzag chains running parallel to the b axis by intermolecular N—H⋯N hydrogen-bond interactions.

Related literature

For related literature, see: Gallagher et al. (2001 ▶); Howarth & Hanlon (2001 ▶); Kazak et al. (2006 ▶); Li et al. (1998 ▶); Íkizler & Sancak (1992 ▶).

Experimental

Crystal data

C₁₄H₉N₃
M _r = 219.24
Monoclinic,
a = 7.2172 (10) Å
b = 11.818 (2) Å
c = 12.719 (2) Å
β = 92.057 (7)°
V = 1084.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.35 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.910, T _max = 1.000 (expected range = 0.903–0.992)
11203 measured reflections
2581 independent reflections
2073 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.118
S = 1.08
2581 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012932/rz2211sup1.cif

e-64-o1017-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012932/rz2211Isup2.hkl

e-64-o1017-Isup2.hkl^{(126.8KB, 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
C13—H13A⋯N1	0.93	2.54	2.861 (2)	101
N2—H2A⋯N3ⁱ	0.910 (17)	2.14 (2)	3.033 (2)	169.1 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a Start-up Grant from SEU to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Benzimidazole systems continue to attract much attention in chemical synthesis, structural science and applied biological research (Li et al., 1998; Gallagher et al., 2001; Howarth & Hanlon, 2001; Kazak et al., 2006). Nitriles are parent compounds for the preparation of various functional organic materials having triazole, imidazole or thidiazole moieties (Íkizler & Sancak, 1992) and their derivatives have found many industrial applications. We report here the crystal structure of the title compound, 4-(1H-benzo[d]imidazol-2-yl) benzonitrile.

The structural analysis shows that in the title compound (Fig. 1) the benzimidazole ring system and the phenyl ring are nearly coplanar, the dihedral angle they form being 3.87 (3)°. In the imidazole ring, the C7δb N1 bond length of 1.3191 (16) Å conforms to the value for a double bond. The molecular conformation is stabilized by an intramolecular C—H..N hydrogen bond (Table 1). In the crystal structure, molecules are linked into zig-zag chains running parallel to the b axis by intermolecular N—H···N hydrogen bonding interactions involving the protonated N atom of the imidazole ring as H-donor and the N atom of the nitrile group as acceptor.

Experimental

4-Formylbenzonitrile (2 mmol), malononitrile (1 mmol) and benzene-1,2-diamine (1 mmol) were heated at 100°C with stirring for 5 min. The mixture was washed with dichloromethane(5 mL) and dried. A white solid was obtained after recrystallization from ethanol. 4-(1H-Benzo[d]imidazol-2-yl)benzonitrile (0.3 mmol) was placed in a thick-walled Pyrex tube. EtOH (0.3 mL) and H₂O (0.3 mL) were then added, the tube was frozen with liquid N₂, evacuated and flame-sealed. The tube was heated at 100°C for 2 days to give colourless crystals of the title compound.