1-(4-Methyl-benz-yl)-1H-benzimidazol-2(3H)-one.

In the title compound, C15H14N2O, the fused five- and six-membered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å. The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6)°. In the crystal, inversion dimers are formed by pairs of N-H⋯O hydrogen bonds; these dimers are linked by weak C-H⋯O inter-actions into a two-dimensional array in the (102) plane.

Related literature

For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al. (2004 ▶); Deligeorgiev et al. (2011 ▶); Scott et al. (2002 ▶); Gothelf et al. (1998 ▶). For related structures, see: Belaziz et al. (2012 ▶); Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C15H14N2O

M = 238.28

Monoclinic,

a = 12.5585 (5) Å

b = 5.7181 (2) Å

c = 17.4153 (7) Å

β = 95.277 (2)°

V = 1245.31 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.51 × 0.42 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer

16486 measured reflections

3211 independent reflections

2157 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.02

3211 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip,2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050726/tk5182sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050726/tk5182Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050726/tk5182Isup3.cml

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

C15H14N2O	F(000) = 504
Mr = 238.28	Dx = 1.271 Mg m−3
Monoclinic, P21/n	Melting point: 456 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5585 (5) Å	Cell parameters from 3211 reflections
b = 5.7181 (2) Å	θ = 3.3–28.7°
c = 17.4153 (7) Å	µ = 0.08 mm−1
β = 95.277 (2)°	T = 296 K
V = 1245.31 (8) Å3	Block, colourless
Z = 4	0.51 × 0.42 × 0.15 mm

Bruker X8 APEXII diffractometer	2157 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.7°, θmin = 3.3°
φ and ω scans	h = −16→10
16486 measured reflections	k = −7→7
3211 independent reflections	l = −23→23

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2271P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3211 reflections	Δρmax = 0.17 e Å−3
164 parameters	Δρmin = −0.15 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: 0.0047 (19)

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	0.40817 (8)	0.80403 (18)	0.04185 (6)	0.0541 (3)
N1	0.59419 (10)	0.8138 (2)	0.06169 (7)	0.0456 (3)
H1N1	0.6036	0.9478	0.0317	0.055*
C6	0.67241 (12)	0.6686 (2)	0.09809 (7)	0.0416 (3)
N2	0.50984 (9)	0.51864 (19)	0.10975 (6)	0.0425 (3)
C9	0.41188 (10)	0.3448 (2)	0.21353 (8)	0.0399 (3)
C5	0.61861 (11)	0.4813 (2)	0.12841 (7)	0.0405 (3)
C8	0.42295 (12)	0.3671 (2)	0.12812 (8)	0.0475 (4)
H8A	0.4343	0.2127	0.1073	0.057*
H8B	0.3565	0.4273	0.1029	0.057*
C4	0.67330 (13)	0.3032 (3)	0.16849 (8)	0.0498 (4)
H4	0.6375	0.1783	0.1886	0.060*
C14	0.44588 (12)	0.5170 (2)	0.26587 (8)	0.0498 (4)
H14	0.4778	0.6517	0.2487	0.060*
C10	0.36386 (12)	0.1473 (3)	0.24098 (9)	0.0500 (4)
H10	0.3403	0.0291	0.2069	0.060*
C7	0.49498 (12)	0.7221 (2)	0.06784 (8)	0.0425 (3)
C1	0.78212 (12)	0.6843 (3)	0.10756 (9)	0.0518 (4)
H1	0.8181	0.8099	0.0879	0.062*
C3	0.78367 (13)	0.3187 (3)	0.17738 (9)	0.0568 (4)
H3	0.8228	0.2012	0.2039	0.068*
C12	0.38486 (12)	0.2947 (3)	0.37129 (9)	0.0568 (4)
C2	0.83703 (13)	0.5043 (3)	0.14782 (9)	0.0581 (4)
H2	0.9113	0.5093	0.1550	0.070*
C11	0.35059 (12)	0.1242 (3)	0.31856 (9)	0.0582 (4)
H11	0.3178	−0.0095	0.3356	0.070*
C13	0.43294 (13)	0.4911 (3)	0.34360 (9)	0.0580 (4)
H13	0.4571	0.6084	0.3779	0.070*
C15	0.37084 (17)	0.2654 (5)	0.45607 (11)	0.0944 (7)
H15A	0.3991	0.4000	0.4839	0.142*
H15B	0.4084	0.1281	0.4753	0.142*
H15C	0.2962	0.2495	0.4628	0.142*

	U11	U22	U33	U12	U13	U23
O1	0.0523 (7)	0.0521 (6)	0.0563 (6)	0.0055 (5)	−0.0040 (5)	0.0144 (5)
N1	0.0529 (8)	0.0409 (6)	0.0424 (7)	0.0004 (5)	0.0018 (5)	0.0097 (5)
C6	0.0511 (9)	0.0410 (7)	0.0326 (7)	0.0025 (6)	0.0027 (6)	−0.0010 (5)
N2	0.0466 (7)	0.0404 (6)	0.0399 (6)	0.0001 (5)	0.0003 (5)	0.0076 (5)
C9	0.0376 (8)	0.0381 (7)	0.0431 (8)	0.0002 (5)	−0.0018 (6)	0.0029 (5)
C5	0.0484 (9)	0.0403 (7)	0.0323 (7)	0.0019 (6)	0.0006 (6)	−0.0010 (5)
C8	0.0535 (9)	0.0437 (7)	0.0440 (8)	−0.0072 (6)	−0.0024 (7)	0.0014 (6)
C4	0.0621 (10)	0.0427 (8)	0.0432 (8)	0.0042 (6)	−0.0029 (7)	0.0051 (6)
C14	0.0565 (10)	0.0425 (8)	0.0497 (9)	−0.0090 (6)	0.0009 (7)	−0.0003 (6)
C10	0.0496 (9)	0.0448 (8)	0.0542 (9)	−0.0094 (6)	−0.0019 (7)	0.0020 (6)
C7	0.0520 (9)	0.0398 (7)	0.0348 (7)	0.0029 (6)	0.0000 (6)	0.0033 (5)
C1	0.0519 (10)	0.0568 (9)	0.0471 (9)	−0.0046 (7)	0.0063 (7)	−0.0004 (6)
C3	0.0599 (11)	0.0558 (9)	0.0526 (9)	0.0145 (7)	−0.0063 (8)	0.0023 (7)
C12	0.0410 (9)	0.0808 (12)	0.0485 (9)	0.0004 (8)	0.0044 (7)	0.0068 (8)
C2	0.0490 (10)	0.0715 (11)	0.0529 (9)	0.0090 (8)	0.0000 (7)	−0.0049 (8)
C11	0.0481 (10)	0.0646 (10)	0.0619 (11)	−0.0107 (7)	0.0054 (8)	0.0173 (8)
C13	0.0599 (11)	0.0654 (10)	0.0478 (9)	−0.0044 (8)	−0.0003 (7)	−0.0104 (7)
C15	0.0829 (15)	0.148 (2)	0.0539 (12)	−0.0091 (14)	0.0142 (10)	0.0111 (12)

O1—C7	1.2338 (16)	C14—C13	1.386 (2)
N1—C7	1.3649 (18)	C14—H14	0.9300
N1—C6	1.3933 (17)	C10—C11	1.383 (2)
N1—H1N1	0.9411	C10—H10	0.9300
C6—C1	1.375 (2)	C1—C2	1.392 (2)
C6—C5	1.3959 (19)	C1—H1	0.9300
N2—C7	1.3770 (16)	C3—C2	1.380 (2)
N2—C5	1.3913 (17)	C3—H3	0.9300
N2—C8	1.4521 (17)	C12—C11	1.381 (2)
C9—C14	1.3822 (19)	C12—C13	1.383 (2)
C9—C10	1.3857 (19)	C12—C15	1.512 (2)
C9—C8	1.5120 (19)	C2—H2	0.9300
C5—C4	1.3811 (18)	C11—H11	0.9300
C8—H8A	0.9700	C13—H13	0.9300
C8—H8B	0.9700	C15—H15A	0.9600
C4—C3	1.383 (2)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C7—N1—C6	110.24 (11)	C9—C10—H10	119.7
C7—N1—H1N1	121.3	O1—C7—N1	127.42 (13)
C6—N1—H1N1	128.2	O1—C7—N2	125.97 (13)
C1—C6—N1	132.24 (13)	N1—C7—N2	106.61 (12)
C1—C6—C5	121.27 (13)	C6—C1—C2	117.16 (14)
N1—C6—C5	106.49 (12)	C6—C1—H1	121.4
C7—N2—C5	109.63 (11)	C2—C1—H1	121.4
C7—N2—C8	123.58 (12)	C2—C3—C4	121.57 (14)
C5—N2—C8	126.76 (11)	C2—C3—H3	119.2
C14—C9—C10	118.08 (13)	C4—C3—H3	119.2
C14—C9—C8	122.55 (12)	C11—C12—C13	117.44 (15)
C10—C9—C8	119.36 (12)	C11—C12—C15	120.94 (18)
C4—C5—N2	131.55 (13)	C13—C12—C15	121.61 (17)
C4—C5—C6	121.43 (14)	C3—C2—C1	121.44 (15)
N2—C5—C6	107.02 (11)	C3—C2—H2	119.3
N2—C8—C9	113.95 (11)	C1—C2—H2	119.3
N2—C8—H8A	108.8	C12—C11—C10	121.61 (15)
C9—C8—H8A	108.8	C12—C11—H11	119.2
N2—C8—H8B	108.8	C10—C11—H11	119.2
C9—C8—H8B	108.8	C12—C13—C14	121.43 (15)
H8A—C8—H8B	107.7	C12—C13—H13	119.3
C5—C4—C3	117.12 (14)	C14—C13—H13	119.3
C5—C4—H4	121.4	C12—C15—H15A	109.5
C3—C4—H4	121.4	C12—C15—H15B	109.5
C9—C14—C13	120.74 (14)	H15A—C15—H15B	109.5
C9—C14—H14	119.6	C12—C15—H15C	109.5
C13—C14—H14	119.6	H15A—C15—H15C	109.5
C11—C10—C9	120.69 (14)	H15B—C15—H15C	109.5
C11—C10—H10	119.7
C7—N1—C6—C1	−179.97 (14)	C8—C9—C10—C11	−178.65 (14)
C7—N1—C6—C5	−0.56 (15)	C6—N1—C7—O1	−179.46 (13)
C7—N2—C5—C4	−179.25 (14)	C6—N1—C7—N2	1.05 (15)
C8—N2—C5—C4	−1.2 (2)	C5—N2—C7—O1	179.35 (13)
C7—N2—C5—C6	0.82 (14)	C8—N2—C7—O1	1.3 (2)
C8—N2—C5—C6	178.83 (12)	C5—N2—C7—N1	−1.15 (15)
C1—C6—C5—C4	−0.6 (2)	C8—N2—C7—N1	−179.24 (12)
N1—C6—C5—C4	179.90 (12)	N1—C6—C1—C2	−179.93 (14)
C1—C6—C5—N2	179.33 (12)	C5—C6—C1—C2	0.7 (2)
N1—C6—C5—N2	−0.16 (14)	C5—C4—C3—C2	0.3 (2)
C7—N2—C8—C9	−117.18 (14)	C4—C3—C2—C1	−0.1 (2)
C5—N2—C8—C9	65.08 (17)	C6—C1—C2—C3	−0.4 (2)
C14—C9—C8—N2	26.23 (19)	C13—C12—C11—C10	0.2 (2)
C10—C9—C8—N2	−155.20 (13)	C15—C12—C11—C10	−179.31 (17)
N2—C5—C4—C3	−179.82 (14)	C9—C10—C11—C12	−0.4 (2)
C6—C5—C4—C3	0.1 (2)	C11—C12—C13—C14	0.3 (2)
C10—C9—C14—C13	0.5 (2)	C15—C12—C13—C14	179.84 (16)
C8—C9—C14—C13	179.13 (14)	C9—C14—C13—C12	−0.7 (2)
C14—C9—C10—C11	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.94	1.91	2.8317 (15)	166
C15—H15C···O1ii	0.96	2.58	3.514 (2)	165
C8—H8A···O1iii	0.97	2.61	3.5504 (18)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.94	1.91	2.8317 (15)	166
C15—H15C⋯O1ii	0.96	2.58	3.514 (2)	165
C8—H8A⋯O1iii	0.97	2.61	3.5504 (18)	164

Symmetry codes: (i) ; (ii) ; (iii) .