2-p-Tolyl-1-p-tolyl­methyl-1H-benzimidazole

Ting Liu

doi:10.1107/S1600536809021175

. 2009 Jun 27;65(Pt 7):o1688. doi: 10.1107/S1600536809021175

2-p-Tolyl-1-p-tolylmethyl-1H-benzimidazole

Ting Liu ^a,^*

PMCID: PMC2969414 PMID: 21582944

Abstract

The asymmetric unit of the title compound, C₂₂H₂₀N₂, contains two crystallographically independent molecules in which the planar benzimidazole ring systems are oriented with respect to the adjacent tolyl rings at dihedral angles of 47.08 (8)/76.85 (8) and 39.52 (9)/87.49 (9)°, while the dihedral angles between the tolyl rings are 73.99 (3) and 81.51 (9)°. In the crystal structure, pairs of intermolecular C—H⋯N interactions link one of the asymmetric molecules into centrosymmetric dimers through R ₂ ²(8) ring motifs.

Related literature

For general background to the biological and pharmaceutical activities of benzimidazole derivatives, see: Matsuno et al. (2000 ▶). Garuti et al. (1999 ▶). For related structures, see: Tlahuext et al. (2007 ▶); Chen & Ruan (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₂H₂₀N₂
M _r = 312.40
Triclinic,
a = 9.7046 (19) Å
b = 10.457 (2) Å
c = 17.825 (4) Å
α = 84.12 (3)°
β = 81.44 (3)°
γ = 75.87 (3)°
V = 1730.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 K
0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.984, T _max = 0.988
16221 measured reflections
6773 independent reflections
3812 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.173
S = 1.01
6773 reflections
434 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 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/S1600536809021175/hk2704sup1.cif

e-65-o1688-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021175/hk2704Isup2.hkl

e-65-o1688-Isup2.hkl^{(331.4KB, 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
C35—H35A⋯N3ⁱ	0.93	2.60	3.491 (3)	162

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Benzimidazole derivatives have attracted considerable attention because of their biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999). In addition, they play an important role in the development of coordination chemistry. Many derivatives of benzimidazole have been prepared and their complexes have been studied (Tlahuext et al., 2007; Chen & Ruan, 2007). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/N2/C8/C9/C14), C (C9-C14), D (C16-C21) and E (C23-C28), F (N3/N4/C30/C31/C36), G (C31-C36), H (C38-C43) are, of course, planar. The planar benzimidazole ring systems, (N1/N2/C8-C14) and (N3/N4/C30-C36), are oriented with respect to the adjacent rings, A, D and E, H, at dihedral angles of 47.08 (8), 76.85 (8) ° and 39.52 (9), 87.49 (9) °, respectively, while the dihedral angles between rings A, D and E, H are 73.99 (3) and 81.51 (9) °, respectively.

In the crystal structure, intermolecular C-H···N interactions (Table 1) link the molecules into centrosymmetric dimers through R₂²(8) ring motifs (Bernstein et al., 1995) (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, 4-methylbenzaldehyde(0.96 g, 8 mmol) was added to a solution of o-phenylenediamine (0.432 g, 4 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for 4 h. When cooled to room temperature, the resultant solution was filtered and allowed to evaporate slowly. Crystals suitable for X-ray analysis were obtained after several weeks.