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, mol-ecules are linked into chains along the a-axis direction by weak C-H⋯N inter-actions. The crystal structure also features C-H⋯π inter-actions.

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 = 284.35

Orthorhombic,

a = 15.6755 (4) Å

b = 9.3509 (6) Å

c = 21.1976 (8) Å

V = 3107.1 (2) Å3

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.01

2523 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300264X/fy2081sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300264X/fy2081Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300264X/fy2081Isup3.cml

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

C20H16N2	F(000) = 1200
Mr = 284.35	Dx = 1.216 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3879 reflections
a = 15.6755 (4) Å	θ = 2.7–22.5°
b = 9.3509 (6) Å	µ = 0.07 mm−1
c = 21.1976 (8) Å	T = 293 K
V = 3107.1 (2) Å3	Block, colourless
Z = 8	0.30 × 0.30 × 0.25 mm

Bruker Kappa APEXII diffractometer	2523 independent reflections
Radiation source: rotating anode	1840 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 18.4 pixels mm-1	θmax = 24.3°, θmin = 2.3°
ω and φ scan	h = −18→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −8→10
Tmin = 0.966, Tmax = 0.997	l = −24→18
15284 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.5482P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2523 reflections	Δρmax = 0.12 e Å−3
201 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (6)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.14753 (9)	−0.13901 (15)	0.07038 (6)	0.0552 (5)
N2	0.09742 (9)	0.08161 (13)	0.08884 (6)	0.0487 (5)
C1	0.12646 (10)	−0.12606 (18)	0.13367 (8)	0.0531 (6)
C2	0.13195 (12)	−0.2254 (2)	0.18248 (9)	0.0672 (7)
C3	0.10524 (14)	−0.1835 (2)	0.24119 (9)	0.0743 (8)
C4	0.07406 (13)	−0.0470 (2)	0.25226 (9)	0.0751 (8)
C5	0.06882 (11)	0.0531 (2)	0.20511 (8)	0.0641 (7)
C6	0.09523 (10)	0.01008 (17)	0.14593 (7)	0.0507 (6)
C7	0.12994 (9)	−0.01370 (17)	0.04511 (7)	0.0472 (6)
C8	0.14252 (10)	0.01833 (17)	−0.02203 (7)	0.0470 (5)
C9	0.09213 (11)	0.11433 (17)	−0.05513 (8)	0.0536 (6)
C10	0.10375 (12)	0.13481 (18)	−0.11886 (8)	0.0569 (6)
C11	0.16546 (11)	0.06158 (19)	−0.15234 (8)	0.0562 (6)
C12	0.21529 (11)	−0.0342 (2)	−0.11910 (8)	0.0647 (7)
C13	0.20433 (11)	−0.05620 (19)	−0.05528 (8)	0.0597 (7)
C14	0.17583 (14)	0.0840 (2)	−0.22227 (9)	0.0782 (8)
C15	0.07647 (10)	0.22994 (17)	0.08275 (7)	0.0473 (6)
C16	0.14063 (13)	0.32822 (19)	0.07561 (8)	0.0615 (7)
C17	0.12051 (17)	0.4708 (2)	0.07146 (9)	0.0791 (9)
C18	0.03838 (19)	0.5144 (2)	0.07484 (9)	0.0793 (9)
C19	−0.02647 (15)	0.4162 (2)	0.08192 (8)	0.0741 (8)
C20	−0.00744 (12)	0.2715 (2)	0.08613 (7)	0.0586 (7)
H2	0.15302	−0.31698	0.17546	0.0806*
H3	0.10809	−0.24820	0.27444	0.0892*
H4	0.05623	−0.02266	0.29271	0.0901*
H5	0.04856	0.14504	0.21259	0.0769*
H9	0.04999	0.16546	−0.03403	0.0642*
H10	0.06909	0.19980	−0.13997	0.0683*
H12	0.25734	−0.08529	−0.14034	0.0777*
H13	0.23879	−0.12174	−0.03432	0.0717*
H14A	0.12372	0.05913	−0.24338	0.1173*
H14B	0.22126	0.02453	−0.23762	0.1173*
H14C	0.18915	0.18246	−0.23039	0.1173*
H16	0.19721	0.29863	0.07359	0.0738*
H17	0.16371	0.53792	0.06628	0.0949*
H18	0.02558	0.61134	0.07237	0.0949*
H19	−0.08286	0.44676	0.08386	0.0889*
H20	−0.05058	0.20415	0.09114	0.0703*

	U11	U22	U33	U12	U13	U23
N1	0.0569 (9)	0.0543 (9)	0.0543 (9)	0.0053 (7)	−0.0008 (7)	0.0016 (7)
N2	0.0514 (8)	0.0480 (8)	0.0466 (8)	−0.0015 (6)	0.0053 (6)	−0.0017 (6)
C1	0.0496 (10)	0.0571 (11)	0.0526 (11)	−0.0049 (8)	−0.0022 (8)	0.0039 (8)
C2	0.0721 (13)	0.0649 (12)	0.0646 (12)	−0.0018 (10)	−0.0062 (10)	0.0113 (10)
C3	0.0794 (14)	0.0847 (15)	0.0589 (13)	−0.0093 (12)	−0.0015 (10)	0.0201 (11)
C4	0.0791 (14)	0.0967 (16)	0.0495 (11)	−0.0075 (12)	0.0088 (9)	0.0050 (11)
C5	0.0679 (13)	0.0721 (12)	0.0522 (11)	−0.0022 (10)	0.0083 (9)	−0.0026 (9)
C6	0.0488 (10)	0.0558 (10)	0.0475 (10)	−0.0053 (8)	0.0034 (8)	0.0010 (8)
C7	0.0415 (9)	0.0499 (10)	0.0501 (10)	−0.0007 (7)	0.0011 (7)	−0.0023 (8)
C8	0.0443 (9)	0.0509 (9)	0.0459 (9)	−0.0013 (7)	0.0003 (7)	−0.0038 (8)
C9	0.0544 (11)	0.0542 (10)	0.0521 (10)	0.0055 (8)	0.0036 (8)	−0.0039 (8)
C10	0.0615 (11)	0.0570 (10)	0.0522 (11)	0.0019 (9)	−0.0021 (8)	0.0026 (8)
C11	0.0537 (11)	0.0655 (11)	0.0494 (10)	−0.0088 (9)	0.0029 (8)	−0.0034 (9)
C12	0.0527 (11)	0.0859 (13)	0.0556 (12)	0.0088 (10)	0.0074 (8)	−0.0126 (10)
C13	0.0517 (11)	0.0727 (12)	0.0548 (11)	0.0128 (9)	−0.0003 (8)	−0.0027 (9)
C14	0.0827 (15)	0.0974 (15)	0.0545 (12)	−0.0074 (12)	0.0090 (10)	0.0015 (10)
C15	0.0540 (11)	0.0474 (10)	0.0404 (9)	−0.0020 (8)	0.0028 (7)	−0.0048 (7)
C16	0.0659 (12)	0.0582 (12)	0.0603 (11)	−0.0100 (9)	0.0070 (9)	−0.0054 (9)
C17	0.112 (2)	0.0552 (12)	0.0700 (13)	−0.0163 (12)	0.0153 (12)	−0.0064 (10)
C18	0.131 (2)	0.0530 (12)	0.0538 (12)	0.0133 (14)	0.0079 (12)	−0.0039 (9)
C19	0.0857 (15)	0.0854 (15)	0.0511 (12)	0.0331 (13)	0.0013 (10)	−0.0125 (10)
C20	0.0570 (12)	0.0664 (12)	0.0525 (10)	0.0050 (9)	0.0034 (8)	−0.0104 (9)

N1—C1	1.387 (2)	C16—C17	1.373 (3)
N1—C7	1.318 (2)	C17—C18	1.352 (4)
N2—C6	1.383 (2)	C18—C19	1.378 (3)
N2—C7	1.383 (2)	C19—C20	1.388 (3)
N2—C15	1.431 (2)	C2—H2	0.9300
C1—C2	1.393 (3)	C3—H3	0.9300
C1—C6	1.389 (2)	C4—H4	0.9300
C2—C3	1.370 (3)	C5—H5	0.9300
C3—C4	1.387 (3)	C9—H9	0.9300
C4—C5	1.372 (3)	C10—H10	0.9300
C5—C6	1.381 (2)	C12—H12	0.9300
C7—C8	1.468 (2)	C13—H13	0.9300
C8—C9	1.386 (2)	C14—H14A	0.9600
C8—C13	1.386 (2)	C14—H14B	0.9600
C9—C10	1.377 (2)	C14—H14C	0.9600
C10—C11	1.381 (2)	C16—H16	0.9300
C11—C12	1.382 (2)	C17—H17	0.9300
C11—C14	1.506 (3)	C18—H18	0.9300
C12—C13	1.379 (2)	C19—H19	0.9300
C15—C16	1.371 (2)	C20—H20	0.9300
C15—C20	1.373 (2)
C1—N1—C7	105.41 (13)	C15—C20—C19	118.57 (18)
C6—N2—C7	106.49 (12)	C1—C2—H2	121.00
C6—N2—C15	122.81 (13)	C3—C2—H2	121.00
C7—N2—C15	130.43 (13)	C2—C3—H3	119.00
N1—C1—C2	130.20 (16)	C4—C3—H3	119.00
N1—C1—C6	110.19 (14)	C3—C4—H4	119.00
C2—C1—C6	119.61 (16)	C5—C4—H4	119.00
C1—C2—C3	117.71 (17)	C4—C5—H5	122.00
C2—C3—C4	121.64 (18)	C6—C5—H5	122.00
C3—C4—C5	121.73 (18)	C8—C9—H9	120.00
C4—C5—C6	116.43 (17)	C10—C9—H9	120.00
N2—C6—C1	105.72 (13)	C9—C10—H10	119.00
N2—C6—C5	131.41 (15)	C11—C10—H10	119.00
C1—C6—C5	122.88 (15)	C11—C12—H12	119.00
N1—C7—N2	112.19 (13)	C13—C12—H12	119.00
N1—C7—C8	123.20 (14)	C8—C13—H13	120.00
N2—C7—C8	124.60 (14)	C12—C13—H13	120.00
C7—C8—C9	123.12 (14)	C11—C14—H14A	109.00
C7—C8—C13	118.97 (14)	C11—C14—H14B	109.00
C9—C8—C13	117.81 (15)	C11—C14—H14C	109.00
C8—C9—C10	120.76 (16)	H14A—C14—H14B	109.00
C9—C10—C11	121.86 (16)	H14A—C14—H14C	110.00
C10—C11—C12	117.08 (16)	H14B—C14—H14C	109.00
C10—C11—C14	120.82 (16)	C15—C16—H16	120.00
C12—C11—C14	122.09 (16)	C17—C16—H16	120.00
C11—C12—C13	121.77 (16)	C16—C17—H17	120.00
C8—C13—C12	120.72 (16)	C18—C17—H17	120.00
N2—C15—C16	119.43 (15)	C17—C18—H18	120.00
N2—C15—C20	119.29 (15)	C19—C18—H18	120.00
C16—C15—C20	121.25 (16)	C18—C19—H19	120.00
C15—C16—C17	119.32 (19)	C20—C19—H19	120.00
C16—C17—C18	120.5 (2)	C15—C20—H20	121.00
C17—C18—C19	120.47 (19)	C19—C20—H20	121.00
C18—C19—C20	119.9 (2)
C7—N1—C1—C2	179.96 (18)	C4—C5—C6—C1	−0.6 (3)
C7—N1—C1—C6	0.33 (18)	C4—C5—C6—N2	179.05 (17)
C1—N1—C7—N2	−0.49 (17)	N2—C7—C8—C13	154.00 (15)
C1—N1—C7—C8	−179.56 (14)	N1—C7—C8—C9	149.15 (16)
C6—N2—C7—N1	0.47 (18)	N1—C7—C8—C13	−27.1 (2)
C15—N2—C7—N1	174.56 (15)	N2—C7—C8—C9	−29.8 (2)
C6—N2—C15—C16	103.65 (18)	C13—C8—C9—C10	−0.3 (2)
C7—N2—C15—C16	−69.6 (2)	C7—C8—C13—C12	176.83 (16)
C6—N2—C15—C20	−74.4 (2)	C7—C8—C9—C10	−176.52 (16)
C7—N2—C15—C20	112.39 (18)	C9—C8—C13—C12	0.4 (3)
C7—N2—C6—C1	−0.23 (17)	C8—C9—C10—C11	0.0 (3)
C15—N2—C6—C1	−174.88 (14)	C9—C10—C11—C12	0.2 (3)
C7—N2—C6—C5	−179.95 (17)	C9—C10—C11—C14	178.90 (17)
C15—N2—C6—C5	5.4 (3)	C14—C11—C12—C13	−178.73 (17)
C6—N2—C7—C8	179.52 (14)	C10—C11—C12—C13	−0.1 (3)
C15—N2—C7—C8	−6.4 (3)	C11—C12—C13—C8	−0.3 (3)
C6—C1—C2—C3	0.4 (3)	N2—C15—C16—C17	−178.28 (15)
N1—C1—C6—C5	179.69 (15)	C20—C15—C16—C17	−0.3 (2)
N1—C1—C6—N2	−0.06 (19)	N2—C15—C20—C19	178.20 (14)
N1—C1—C2—C3	−179.16 (18)	C16—C15—C20—C19	0.2 (2)
C2—C1—C6—C5	0.0 (3)	C15—C16—C17—C18	0.5 (3)
C2—C1—C6—N2	−179.73 (15)	C16—C17—C18—C19	−0.6 (3)
C1—C2—C3—C4	−0.3 (3)	C17—C18—C19—C20	0.5 (3)
C2—C3—C4—C5	−0.4 (3)	C18—C19—C20—C15	−0.3 (2)
C3—C4—C5—C6	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1i	0.9300	2.5000	3.337 (2)	149.00
C20—H20···Cg1ii	0.9300	2.7988	3.707 (2)	165.79

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⋯N1i	0.93	2.50	3.337 (2)	149
C20—H20⋯Cg1ii	0.93	2.80	3.707 (2)	166

Symmetry codes: (i) ; (ii) .