2-(4-Meth-oxy-phen-yl)-1-phenyl-1H-benzimidazole.

In the title compound, C(20)H(16)N(2)O, the 1H-benzimidazole ring forms dihedral angles of 48.00 (6) and 64.48 (6)°, respectively with the benzene and phenyl rings, which are inclined to one another by 58.51 (7)°. In the crystal, weak C-H⋯π inter-actions are the only inter-molecular inter-actions present.

Related literature

For background to benzimidazole derivatives, see: Mason et al. (1999 ▶). For their biological activities such as anti­microbial & anti­cancer, anti­diabetic, anti­fungal, anti HIV and anti­viral, see: Demirayak et al. (2002 ▶); Minoura et al. (2004 ▶); Pawar et al. (2004 ▶); Rao et al. (2003 ▶); Tomei et al. (2003 ▶). For their action as polymerase and transcriptase inhibitors, see: Beaulieu et al. (2004 ▶; Morningstar et al. (2007 ▶); Roth et al. (1997 ▶); For other related studies, see: Jayabharathi et al. (2012 ▶)

Experimental

Crystal data

C20H16N2O

M = 300.35

Monoclinic,

a = 12.3220 (3) Å

b = 7.3030 (2) Å

c = 18.2450 (3) Å

β = 108.909 (1)°

V = 1553.22 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.956, T max = 0.999

13787 measured reflections

2728 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.03

2728 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and 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: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001566/go2077sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001566/go2077Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001566/go2077Isup3.cml

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

C20H16N2O	F(000) = 632
Mr = 300.35	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6267 reflections
a = 12.3220 (3) Å	θ = 2.8–31.8°
b = 7.3030 (2) Å	µ = 0.08 mm−1
c = 18.2450 (3) Å	T = 293 K
β = 108.909 (1)°	Block, colourless
V = 1553.22 (6) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2728 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scan	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.956, Tmax = 0.999	k = −8→8
13787 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.3566P] where P = (Fo2 + 2Fc2)/3
2728 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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
C1	0.15098 (14)	0.1529 (3)	0.11631 (12)	0.0752 (5)
H1A	0.1582	0.0917	0.1642	0.113*
H1B	0.0756	0.1323	0.0803	0.113*
H1C	0.1629	0.2819	0.1256	0.113*
C2	0.34701 (11)	0.10389 (19)	0.12724 (8)	0.0448 (3)
C3	0.42477 (12)	0.0429 (2)	0.09213 (8)	0.0486 (4)
H3	0.3983	−0.0131	0.0438	0.058*
C4	0.54039 (12)	0.0648 (2)	0.12827 (7)	0.0450 (3)
H4	0.5916	0.0255	0.1037	0.054*
C5	0.58222 (11)	0.14511 (18)	0.20131 (7)	0.0385 (3)
C6	0.50382 (12)	0.20005 (19)	0.23664 (8)	0.0443 (3)
H6	0.5302	0.2506	0.2860	0.053*
C7	0.38733 (12)	0.1813 (2)	0.20007 (8)	0.0477 (3)
H7	0.3360	0.2209	0.2245	0.057*
C8	0.70531 (11)	0.17362 (18)	0.24035 (7)	0.0375 (3)
C9	0.87357 (11)	0.18293 (18)	0.32458 (7)	0.0404 (3)
C10	0.96985 (13)	0.1720 (2)	0.39081 (8)	0.0513 (4)
H10	0.9646	0.1228	0.4366	0.062*
C11	1.07235 (13)	0.2354 (2)	0.38684 (9)	0.0557 (4)
H11	1.1373	0.2294	0.4306	0.067*
C12	1.08135 (13)	0.3089 (2)	0.31854 (9)	0.0546 (4)
H12	1.1523	0.3504	0.3178	0.066*
C13	0.98813 (12)	0.3218 (2)	0.25235 (8)	0.0468 (3)
H13	0.9940	0.3716	0.2069	0.056*
C14	0.88502 (11)	0.25677 (18)	0.25688 (7)	0.0377 (3)
C15	0.74297 (10)	0.32860 (18)	0.12689 (7)	0.0365 (3)
C16	0.78572 (13)	0.2560 (2)	0.07224 (7)	0.0478 (4)
H16	0.8363	0.1576	0.0845	0.057*
C17	0.75247 (15)	0.3317 (2)	−0.00127 (8)	0.0589 (4)
H17	0.7807	0.2833	−0.0387	0.071*
C18	0.67873 (15)	0.4765 (3)	−0.01939 (8)	0.0626 (5)
H18	0.6565	0.5259	−0.0690	0.075*
C19	0.63744 (13)	0.5492 (2)	0.03560 (9)	0.0601 (4)
H19	0.5877	0.6488	0.0233	0.072*
C20	0.66926 (11)	0.4754 (2)	0.10932 (8)	0.0479 (4)
H20	0.6411	0.5245	0.1466	0.057*
O1	0.23425 (8)	0.08312 (16)	0.08496 (6)	0.0636 (3)
N1	0.77587 (9)	0.24986 (15)	0.20301 (5)	0.0375 (3)
N2	0.76084 (9)	0.13147 (17)	0.31277 (6)	0.0438 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0447 (6)	0.0665 (8)	0.0712 (7)	−0.0034 (5)	0.0074 (5)	−0.0040 (6)
N1	0.0387 (6)	0.0421 (6)	0.0310 (5)	−0.0019 (5)	0.0105 (4)	0.0038 (4)
N2	0.0489 (7)	0.0512 (7)	0.0316 (5)	0.0002 (5)	0.0134 (5)	0.0035 (5)
C1	0.0459 (9)	0.0666 (12)	0.1100 (15)	0.0005 (8)	0.0207 (9)	−0.0018 (11)
C2	0.0426 (7)	0.0394 (8)	0.0483 (8)	−0.0036 (6)	0.0091 (6)	0.0057 (6)
C3	0.0548 (8)	0.0520 (9)	0.0370 (7)	−0.0121 (7)	0.0121 (6)	−0.0045 (6)
C4	0.0504 (8)	0.0507 (9)	0.0382 (7)	−0.0071 (7)	0.0203 (6)	−0.0039 (6)
C5	0.0442 (7)	0.0388 (7)	0.0336 (6)	−0.0036 (6)	0.0142 (5)	0.0030 (5)
C6	0.0505 (8)	0.0461 (8)	0.0377 (7)	−0.0018 (6)	0.0164 (6)	−0.0038 (6)
C7	0.0478 (8)	0.0461 (8)	0.0532 (8)	0.0027 (7)	0.0220 (7)	−0.0007 (7)
C8	0.0443 (7)	0.0389 (7)	0.0320 (6)	−0.0010 (6)	0.0160 (5)	0.0002 (5)
C9	0.0468 (8)	0.0394 (8)	0.0333 (6)	0.0038 (6)	0.0105 (6)	−0.0006 (5)
C10	0.0566 (9)	0.0547 (9)	0.0376 (7)	0.0092 (7)	0.0080 (6)	0.0033 (6)
C11	0.0471 (8)	0.0577 (10)	0.0498 (8)	0.0081 (7)	−0.0015 (7)	−0.0036 (7)
C12	0.0417 (8)	0.0514 (9)	0.0656 (10)	−0.0010 (7)	0.0103 (7)	−0.0015 (8)
C13	0.0460 (8)	0.0442 (8)	0.0496 (8)	−0.0006 (6)	0.0147 (6)	0.0032 (6)
C14	0.0405 (7)	0.0351 (7)	0.0360 (6)	0.0029 (6)	0.0103 (5)	0.0005 (5)
C15	0.0380 (7)	0.0403 (7)	0.0301 (6)	−0.0067 (6)	0.0095 (5)	0.0032 (5)
C16	0.0587 (9)	0.0471 (9)	0.0419 (7)	−0.0050 (7)	0.0225 (7)	0.0000 (6)
C17	0.0781 (11)	0.0663 (11)	0.0376 (8)	−0.0233 (9)	0.0260 (7)	−0.0047 (7)
C18	0.0695 (10)	0.0707 (12)	0.0367 (8)	−0.0261 (9)	0.0024 (7)	0.0136 (8)
C19	0.0506 (9)	0.0592 (10)	0.0594 (9)	−0.0021 (8)	0.0024 (7)	0.0211 (8)
C20	0.0455 (8)	0.0510 (9)	0.0461 (7)	0.0003 (7)	0.0136 (6)	0.0050 (7)

O1—C1	1.421 (2)	C15—C20	1.374 (2)
O1—C2	1.3616 (18)	C16—C17	1.3842 (19)
N1—C8	1.3835 (17)	C17—C18	1.363 (3)
N1—C14	1.3859 (17)	C18—C19	1.371 (2)
N1—C15	1.4349 (15)	C19—C20	1.383 (2)
N2—C8	1.3126 (16)	C1—H1A	0.9599
N2—C9	1.3868 (18)	C1—H1B	0.9599
C2—C3	1.387 (2)	C1—H1C	0.9600
C2—C7	1.380 (2)	C3—H3	0.9301
C3—C4	1.371 (2)	C4—H4	0.9299
C4—C5	1.3930 (18)	C6—H6	0.9300
C5—C6	1.383 (2)	C7—H7	0.9301
C5—C8	1.4666 (19)	C10—H10	0.9301
C6—C7	1.380 (2)	C11—H11	0.9299
C9—C10	1.395 (2)	C12—H12	0.9302
C9—C14	1.3962 (18)	C13—H13	0.9301
C10—C11	1.369 (2)	C16—H16	0.9298
C11—C12	1.394 (2)	C17—H17	0.9299
C12—C13	1.374 (2)	C18—H18	0.9301
C13—C14	1.384 (2)	C19—H19	0.9297
C15—C16	1.3759 (19)	C20—H20	0.9301
C1—O1—C2	117.99 (13)	C18—C19—C20	120.33 (15)
C8—N1—C14	106.60 (10)	C15—C20—C19	119.28 (13)
C8—N1—C15	127.76 (11)	O1—C1—H1A	109.47
C14—N1—C15	125.22 (11)	O1—C1—H1B	109.47
C8—N2—C9	105.19 (11)	O1—C1—H1C	109.47
O1—C2—C3	115.69 (12)	H1A—C1—H1B	109.48
O1—C2—C7	125.03 (13)	H1A—C1—H1C	109.47
C3—C2—C7	119.28 (13)	H1B—C1—H1C	109.47
C2—C3—C4	120.41 (13)	C2—C3—H3	119.80
C3—C4—C5	120.90 (13)	C4—C3—H3	119.80
C4—C5—C6	118.05 (13)	C3—C4—H4	119.56
C4—C5—C8	121.88 (13)	C5—C4—H4	119.55
C6—C5—C8	120.07 (12)	C5—C6—H6	119.33
C5—C6—C7	121.34 (13)	C7—C6—H6	119.33
C2—C7—C6	119.99 (14)	C2—C7—H7	120.01
N1—C8—N2	112.60 (12)	C6—C7—H7	120.00
N1—C8—C5	122.28 (11)	C9—C10—H10	120.82
N2—C8—C5	125.12 (12)	C11—C10—H10	120.81
N2—C9—C10	130.33 (12)	C10—C11—H11	119.36
N2—C9—C14	110.52 (11)	C12—C11—H11	119.33
C10—C9—C14	119.16 (13)	C11—C12—H12	119.14
C9—C10—C11	118.37 (13)	C13—C12—H12	119.12
C10—C11—C12	121.31 (15)	C12—C13—H13	121.75
C11—C12—C13	121.75 (15)	C14—C13—H13	121.74
C12—C13—C14	116.50 (13)	C15—C16—H16	120.49
N1—C14—C9	105.09 (12)	C17—C16—H16	120.46
N1—C14—C13	131.99 (12)	C16—C17—H17	119.69
C9—C14—C13	122.91 (12)	C18—C17—H17	119.68
N1—C15—C16	119.51 (12)	C17—C18—H18	120.02
N1—C15—C20	119.77 (11)	C19—C18—H18	120.00
C16—C15—C20	120.72 (12)	C18—C19—H19	119.83
C15—C16—C17	119.05 (14)	C20—C19—H19	119.83
C16—C17—C18	120.63 (15)	C15—C20—H20	120.35
C17—C18—C19	119.98 (14)	C19—C20—H20	120.37
C1—O1—C2—C3	−176.41 (14)	C8—C5—C6—C7	177.52 (13)
C1—O1—C2—C7	2.8 (2)	C4—C5—C8—N1	47.29 (19)
C15—N1—C8—N2	−173.11 (12)	C4—C5—C8—N2	−132.70 (15)
C14—N1—C8—C5	179.73 (12)	C4—C5—C6—C7	−1.9 (2)
C8—N1—C14—C9	0.04 (14)	C6—C5—C8—N2	47.9 (2)
C8—N1—C15—C16	−120.52 (15)	C5—C6—C7—C2	1.0 (2)
C14—N1—C15—C16	67.90 (18)	C14—C9—C10—C11	0.3 (2)
C8—N1—C15—C20	59.48 (18)	C10—C9—C14—C13	−0.6 (2)
C14—N1—C15—C20	−112.11 (15)	N2—C9—C14—N1	0.19 (15)
C15—N1—C8—C5	6.9 (2)	C10—C9—C14—N1	−179.49 (12)
C15—N1—C14—C9	173.11 (12)	N2—C9—C10—C11	−179.29 (14)
C8—N1—C14—C13	−178.74 (15)	N2—C9—C14—C13	179.12 (13)
C15—N1—C14—C13	−5.7 (2)	C9—C10—C11—C12	−0.2 (2)
C14—N1—C8—N2	−0.28 (15)	C10—C11—C12—C13	0.3 (2)
C8—N2—C9—C10	179.28 (14)	C11—C12—C13—C14	−0.5 (2)
C9—N2—C8—C5	−179.62 (13)	C12—C13—C14—N1	179.23 (14)
C9—N2—C8—N1	0.39 (15)	C12—C13—C14—C9	0.6 (2)
C8—N2—C9—C14	−0.35 (15)	N1—C15—C16—C17	179.30 (13)
C7—C2—C3—C4	−2.1 (2)	C16—C15—C20—C19	0.5 (2)
C3—C2—C7—C6	1.0 (2)	C20—C15—C16—C17	−0.7 (2)
O1—C2—C7—C6	−178.14 (13)	N1—C15—C20—C19	−179.51 (13)
O1—C2—C3—C4	177.13 (13)	C15—C16—C17—C18	0.2 (2)
C2—C3—C4—C5	1.2 (2)	C16—C17—C18—C19	0.5 (3)
C3—C4—C5—C8	−178.60 (13)	C17—C18—C19—C20	−0.7 (3)
C3—C4—C5—C6	0.8 (2)	C18—C19—C20—C15	0.2 (2)
C6—C5—C8—N1	−132.09 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2i	0.93	2.86	3.5361 (15)	130
C13—H13···Cg3ii	0.93	2.83	3.4594 (16)	126

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C9–C14 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2i	0.93	2.86	3.5361 (15)	130
C13—H13⋯Cg3ii	0.93	2.83	3.4594 (16)	126

Symmetry codes: (i) ; (ii) .