1,3-Dibenzyl-1H-benzimidazol-2(3H)-one.

In the mol-ecular structure of the title compound, C(21)H(18)N(2)O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0121 (9) Å. The O atom and adjacent C atom are located in Wyckoff position 4e on a twofold axis (0, y, 1/4). The two benzyl groups are almost perpendicular to the benzimidazole plane, but point in opposite directions. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 81.95 (5)°, whereas that between the two benzyl groups is 60.96 (7)°.

Related literature

For pharmacological and biochemical properties of benzimidazoles, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). Ouzidan et al. (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C21H18N2O

M = 314.37

Monoclinic,

a = 19.5983 (7) Å

b = 9.0882 (2) Å

c = 10.0473 (3) Å

β = 115.593 (4)°

V = 1613.98 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 200 K

0.37 × 0.21 × 0.15 mm

Data collection

Agilent SuperNova Dual Cu at zero Atlas diffractometer

Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2011) ▶, using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995 ▶)] T min = 0.950, T max = 1.000

7837 measured reflections

1611 independent reflections

1397 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.07

1611 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046071/im2334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046071/im2334Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046071/im2334Isup3.cml

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

C21H18N2O	F(000) = 664
Mr = 314.37	Dx = 1.294 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 5000 reflections
a = 19.5983 (7) Å	θ = 5–50°
b = 9.0882 (2) Å	µ = 0.63 mm−1
c = 10.0473 (3) Å	T = 200 K
β = 115.593 (4)°	Block, colourless
V = 1613.98 (10) Å3	0.37 × 0.21 × 0.15 mm
Z = 4

Agilent SuperNova Dual Cu at zero Atlas diffractometer	1611 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1397 reflections with I > 2σ(I)
mirror	Rint = 0.028
Detector resolution: 10.4051 pixels mm-1	θmax = 73.4°, θmin = 5.0°
ω scans	h = −23→18
Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2011), using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)]	k = −11→11
Tmin = 0.950, Tmax = 1.000	l = −12→12
7837 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4305P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1611 reflections	Δρmax = 0.15 e Å−3
111 parameters	Δρmin = −0.16 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: 0.0010 (2)

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
O1	0.5000	0.58201 (13)	0.2500	0.0492 (4)
N1	0.53746 (5)	0.35600 (11)	0.19370 (10)	0.0366 (3)
C1	0.52407 (6)	0.20943 (12)	0.21516 (11)	0.0333 (3)
C2	0.54925 (7)	0.08014 (14)	0.17958 (13)	0.0390 (3)
H2	0.5835	0.0806	0.1346	0.047*
C3	0.52422 (7)	−0.05071 (14)	0.21593 (14)	0.0432 (3)
H3	0.5402	−0.1444	0.1907	0.052*
C4	0.5000	0.44731 (19)	0.2500	0.0378 (4)
C5	0.58741 (7)	0.40758 (14)	0.13068 (13)	0.0412 (3)
H5A	0.5785	0.5117	0.1088	0.049*
H5B	0.5751	0.3564	0.0384	0.049*
C11	0.67024 (7)	0.38418 (13)	0.23142 (12)	0.0376 (3)
C12	0.71696 (8)	0.30976 (15)	0.18389 (14)	0.0459 (3)
H12	0.6970	0.2694	0.0896	0.055*
C13	0.79366 (8)	0.29464 (16)	0.27566 (17)	0.0522 (4)
H13	0.8249	0.2450	0.2425	0.063*
C14	0.82333 (8)	0.35325 (17)	0.41560 (16)	0.0518 (4)
H14	0.8748	0.3445	0.4765	0.062*
C15	0.77703 (8)	0.42476 (16)	0.46569 (14)	0.0507 (4)
H15	0.7970	0.4626	0.5610	0.061*
C16	0.70099 (8)	0.44026 (15)	0.37424 (14)	0.0450 (3)
H16	0.6699	0.4888	0.4085	0.054*

	U11	U22	U33	U12	U13	U23
O1	0.0546 (8)	0.0361 (7)	0.0477 (7)	0.000	0.0136 (6)	0.000
N1	0.0302 (5)	0.0396 (6)	0.0357 (5)	−0.0023 (4)	0.0103 (4)	0.0015 (4)
C1	0.0233 (5)	0.0391 (6)	0.0293 (5)	−0.0018 (4)	0.0036 (4)	0.0003 (4)
C2	0.0295 (6)	0.0461 (7)	0.0374 (6)	0.0012 (5)	0.0107 (5)	−0.0031 (5)
C3	0.0371 (7)	0.0390 (6)	0.0469 (7)	0.0015 (5)	0.0120 (6)	−0.0036 (5)
C4	0.0329 (9)	0.0390 (9)	0.0311 (8)	0.000	0.0038 (7)	0.000
C5	0.0356 (7)	0.0493 (7)	0.0337 (6)	−0.0049 (5)	0.0101 (5)	0.0064 (5)
C11	0.0331 (6)	0.0406 (6)	0.0349 (6)	−0.0063 (5)	0.0106 (5)	0.0064 (5)
C12	0.0424 (7)	0.0531 (8)	0.0415 (6)	−0.0052 (6)	0.0174 (6)	0.0003 (6)
C13	0.0403 (8)	0.0581 (9)	0.0592 (8)	0.0011 (6)	0.0224 (7)	0.0053 (7)
C14	0.0336 (7)	0.0607 (9)	0.0511 (8)	−0.0050 (6)	0.0088 (6)	0.0129 (6)
C15	0.0412 (7)	0.0618 (9)	0.0377 (7)	−0.0089 (6)	0.0065 (6)	0.0011 (6)
C16	0.0393 (7)	0.0527 (7)	0.0397 (7)	−0.0028 (6)	0.0139 (6)	0.0000 (6)

O1—C4	1.224 (2)	C5—H5B	0.9700
N1—C4	1.3807 (14)	C11—C12	1.3790 (19)
N1—C1	1.3924 (15)	C11—C16	1.3910 (18)
N1—C5	1.4541 (15)	C12—C13	1.3896 (19)
C1—C2	1.3801 (17)	C12—H12	0.9300
C1—C1i	1.397 (2)	C13—C14	1.376 (2)
C2—C3	1.3939 (18)	C13—H13	0.9300
C2—H2	0.9576	C14—C15	1.376 (2)
C3—C3i	1.390 (3)	C14—H14	0.9300
C3—H3	0.9773	C15—C16	1.3790 (18)
C4—N1i	1.3807 (14)	C15—H15	0.9300
C5—C11	1.5118 (17)	C16—H16	0.9300
C5—H5A	0.9700
C4—N1—C1	110.02 (10)	H5A—C5—H5B	107.8
C4—N1—C5	124.18 (11)	C12—C11—C16	118.71 (12)
C1—N1—C5	125.68 (10)	C12—C11—C5	121.24 (11)
C2—C1—N1	131.45 (11)	C16—C11—C5	120.04 (12)
C2—C1—C1i	121.63 (7)	C11—C12—C13	120.56 (12)
N1—C1—C1i	106.92 (6)	C11—C12—H12	119.7
C1—C2—C3	116.92 (12)	C13—C12—H12	119.7
C1—C2—H2	121.4	C14—C13—C12	119.89 (14)
C3—C2—H2	121.7	C14—C13—H13	120.1
C3i—C3—C2	121.44 (8)	C12—C13—H13	120.1
C3i—C3—H3	119.4	C13—C14—C15	120.15 (13)
C2—C3—H3	119.1	C13—C14—H14	119.9
O1—C4—N1i	126.94 (7)	C15—C14—H14	119.9
O1—C4—N1	126.94 (7)	C14—C15—C16	119.88 (13)
N1i—C4—N1	106.12 (14)	C14—C15—H15	120.1
N1—C5—C11	113.16 (9)	C16—C15—H15	120.1
N1—C5—H5A	108.9	C15—C16—C11	120.78 (13)
C11—C5—H5A	108.9	C15—C16—H16	119.6
N1—C5—H5B	108.9	C11—C16—H16	119.6
C11—C5—H5B	108.9