1-Benzyl-1H-benzimidazol-2(3H)-one.

The fused five- and six-membered rings in the title compound, C(14)H(12)N(2)O, are essentially planar, the largest deviation from the mean plane being 0.023 (2) Å. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 68.50 (6)°. In the crystal, each mol-ecule is linked to its symmetry equivalent created by a crystallographic inversion center by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For related structures, see: Ouzidan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C14H12N2O

M = 224.26

Monoclinic,

a = 13.8652 (7) Å

b = 5.7975 (3) Å

c = 14.9337 (7) Å

β = 109.5346 (12)°

V = 1131.33 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.44 × 0.28 mm

Data collection

Bruker CCD three-circle diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.977

9007 measured reflections

3392 independent reflections

2514 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.05

3392 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102455X/im2298sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102455X/im2298Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102455X/im2298Isup3.cml

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

C14H12N2O	F(000) = 472
Mr = 224.26	Dx = 1.317 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3392 reflections
a = 13.8652 (7) Å	θ = 1.7–30.5°
b = 5.7975 (3) Å	µ = 0.09 mm−1
c = 14.9337 (7) Å	T = 298 K
β = 109.5346 (12)°	Prism, colourless
V = 1131.33 (10) Å3	0.50 × 0.44 × 0.28 mm
Z = 4

Bruker CCD three-circle diffractometer	3392 independent reflections
Radiation source: fine-focus sealed tube	2514 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 30.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
Tmin = 0.959, Tmax = 0.977	k = −8→8
9007 measured reflections	l = −16→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1866P] where P = (Fo2 + 2Fc2)/3
3392 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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	0.59908 (7)	0.79068 (16)	0.53088 (6)	0.0462 (2)
N1	0.46509 (7)	0.82117 (17)	0.38695 (7)	0.0391 (2)
H1	0.4387	0.9497	0.3958	0.066 (5)*
C1	0.54932 (8)	0.72077 (19)	0.45072 (8)	0.0354 (2)
N2	0.56888 (7)	0.52373 (16)	0.40851 (7)	0.0350 (2)
C2	0.49440 (8)	0.49698 (19)	0.31953 (8)	0.0343 (2)
C3	0.47930 (10)	0.3259 (2)	0.25181 (9)	0.0429 (3)
H3	0.5232	0.2003	0.2611	0.050 (4)*
C4	0.39558 (11)	0.3498 (3)	0.16918 (9)	0.0513 (3)
H4	0.3834	0.2382	0.1220	0.060 (4)*
C5	0.32981 (10)	0.5368 (3)	0.15565 (9)	0.0510 (3)
H5	0.2745	0.5477	0.0995	0.058 (4)*
C6	0.34472 (10)	0.7081 (2)	0.22409 (9)	0.0455 (3)
H6	0.3002	0.8326	0.2151	0.056 (4)*
C7	0.42820 (9)	0.68586 (19)	0.30576 (8)	0.0357 (2)
C8	0.64791 (9)	0.3581 (2)	0.45689 (8)	0.0378 (2)
H8A	0.6173	0.2060	0.4513	0.044 (4)*
H8B	0.6744	0.3968	0.5239	0.041 (3)*
C11	0.73601 (8)	0.34906 (19)	0.41875 (8)	0.0354 (2)
C12	0.75053 (11)	0.1565 (2)	0.36992 (10)	0.0491 (3)
H12	0.7048	0.0339	0.3591	0.061 (5)*
C13	0.83286 (13)	0.1452 (3)	0.33705 (12)	0.0638 (4)
H13	0.8416	0.0160	0.3036	0.088 (6)*
C14	0.90122 (13)	0.3235 (3)	0.35368 (12)	0.0659 (4)
H14	0.9569	0.3145	0.3324	0.085 (6)*
C15	0.88757 (11)	0.5165 (3)	0.40199 (12)	0.0597 (4)
H15	0.9338	0.6382	0.4129	0.068 (5)*
C16	0.80491 (10)	0.5294 (2)	0.43437 (10)	0.0459 (3)
H16	0.7958	0.6601	0.4668	0.054 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0430 (5)	0.0475 (5)	0.0452 (5)	−0.0005 (4)	0.0110 (4)	−0.0138 (4)
N1	0.0386 (5)	0.0356 (5)	0.0443 (5)	0.0044 (4)	0.0155 (4)	−0.0033 (4)
C1	0.0336 (5)	0.0348 (5)	0.0411 (6)	−0.0025 (4)	0.0171 (5)	−0.0040 (4)
N2	0.0330 (4)	0.0349 (5)	0.0367 (5)	0.0019 (4)	0.0114 (4)	−0.0035 (4)
C2	0.0326 (5)	0.0368 (5)	0.0347 (5)	−0.0011 (4)	0.0130 (4)	0.0000 (4)
C3	0.0447 (6)	0.0405 (6)	0.0429 (6)	0.0018 (5)	0.0137 (5)	−0.0065 (5)
C4	0.0515 (7)	0.0566 (8)	0.0422 (7)	−0.0042 (6)	0.0109 (6)	−0.0116 (6)
C5	0.0412 (6)	0.0656 (9)	0.0404 (6)	−0.0013 (6)	0.0060 (5)	0.0005 (6)
C6	0.0381 (6)	0.0500 (7)	0.0479 (7)	0.0064 (5)	0.0134 (5)	0.0065 (6)
C7	0.0346 (5)	0.0364 (5)	0.0395 (6)	−0.0003 (4)	0.0167 (5)	0.0006 (4)
C8	0.0389 (6)	0.0371 (6)	0.0384 (6)	0.0039 (4)	0.0141 (5)	0.0041 (5)
C11	0.0356 (5)	0.0365 (5)	0.0327 (5)	0.0070 (4)	0.0094 (4)	0.0053 (4)
C12	0.0516 (7)	0.0422 (7)	0.0547 (8)	0.0073 (6)	0.0195 (6)	−0.0022 (6)
C13	0.0697 (10)	0.0637 (9)	0.0675 (9)	0.0226 (8)	0.0354 (8)	−0.0002 (8)
C14	0.0551 (9)	0.0814 (11)	0.0728 (10)	0.0221 (8)	0.0367 (8)	0.0184 (9)
C15	0.0445 (7)	0.0656 (9)	0.0710 (10)	−0.0033 (7)	0.0221 (7)	0.0141 (8)
C16	0.0446 (7)	0.0432 (6)	0.0499 (7)	0.0009 (5)	0.0158 (5)	0.0008 (5)

O1—C1	1.2332 (14)	C6—H6	0.9300
N1—C1	1.3660 (15)	C8—C11	1.5114 (15)
N1—C7	1.3901 (15)	C8—H8A	0.9700
N1—H1	0.8600	C8—H8B	0.9700
C1—N2	1.3749 (14)	C11—C16	1.3824 (17)
N2—C2	1.3922 (14)	C11—C12	1.3845 (17)
N2—C8	1.4546 (14)	C12—C13	1.387 (2)
C2—C3	1.3815 (16)	C12—H12	0.9300
C2—C7	1.3991 (15)	C13—C14	1.368 (3)
C3—C4	1.3897 (19)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.379 (2)
C4—C5	1.387 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.3869 (19)
C5—C6	1.3902 (19)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.3783 (17)
C1—N1—C7	110.31 (9)	N1—C7—C2	106.35 (10)
C1—N1—H1	124.8	N2—C8—C11	113.90 (9)
C7—N1—H1	124.8	N2—C8—H8A	108.8
O1—C1—N1	127.38 (11)	C11—C8—H8A	108.8
O1—C1—N2	125.88 (11)	N2—C8—H8B	108.8
N1—C1—N2	106.74 (10)	C11—C8—H8B	108.8
C1—N2—C2	109.46 (9)	H8A—C8—H8B	107.7
C1—N2—C8	123.52 (10)	C16—C11—C12	119.00 (11)
C2—N2—C8	126.56 (9)	C16—C11—C8	120.68 (11)
C3—C2—N2	131.39 (10)	C12—C11—C8	120.30 (11)
C3—C2—C7	121.52 (11)	C11—C12—C13	120.43 (14)
N2—C2—C7	107.09 (9)	C11—C12—H12	119.8
C2—C3—C4	117.10 (11)	C13—C12—H12	119.8
C2—C3—H3	121.5	C14—C13—C12	120.16 (14)
C4—C3—H3	121.5	C14—C13—H13	119.9
C5—C4—C3	121.38 (12)	C12—C13—H13	119.9
C5—C4—H4	119.3	C13—C14—C15	120.03 (14)
C3—C4—H4	119.3	C13—C14—H14	120.0
C4—C5—C6	121.48 (12)	C15—C14—H14	120.0
C4—C5—H5	119.3	C14—C15—C16	120.02 (14)
C6—C5—H5	119.3	C14—C15—H15	120.0
C7—C6—C5	117.27 (11)	C16—C15—H15	120.0
C7—C6—H6	121.4	C11—C16—C15	120.36 (13)
C5—C6—H6	121.4	C11—C16—H16	119.8
C6—C7—N1	132.40 (11)	C15—C16—H16	119.8
C6—C7—C2	121.25 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.03	2.845 (1)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.03	2.845 (1)	158

Symmetry code: (i) .