1-Phenyl-2-p-tolyl-1H-benzimidazole

In the title compound, C₂₀H₁₆N₂, the benzimidazole ring system forms dihedral angles of 28.50 (7) and 72.44 (7)° with the tolyl and phenyl rings, respectively. In the crystal, mol­ecules are linked into chains along the a-axis direction by weak C—H⋯N inter­actions. The crystal structure also features C—H⋯π inter­actions.

Related literature

For applications of benzimidazole derivatives, see: Fang et al. (2007); Ge et al. (2008); Lai et al. (2008); Shin et al. (2007). For their biological activity, see: Garuti et al. (1999); Matsuno et al. (2000) and for their therapeutic applications, see: Can-Eke et al. (1998); Richter (1997). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

• C₂₀H₁₆N₂

• M_r = 284.35

• Orthorhombic, P b c a

• a = 15.6755 (4) Å

• b = 9.3509 (6) Å

• c = 21.1976 (8) Å

• V = 3107.1 (2) ų

• Z = 8

• Mo Kα radiation

• μ = 0.07 mm⁻¹

• T = 293 K

• 0.30 × 0.30 × 0.25 mm

Data collection

• Bruker Kappa APEXII diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.966, T_max = 0.997

• 15284 measured reflections

• 2523 independent reflections

• 1840 reflections with I > 2σ(I)

• R_int = 0.034

Refinement

• R[F² > 2σ(F²)] = 0.036

• wR(F²) = 0.103

• S = 1.01

• 2523 reflections

• 201 parameters

• H-atom parameters constrained

• Δρ_max = 0.12 e Å⁻³

• Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N1^i	0.93	2.50	3.337 (2)	149
C20—H20⋯Cg1^ii	0.93	2.80	3.707 (2)	166
Symmetry codes: (i) ; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.