1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one.

In the title compound, C17H16N2O, the fused benzimidazol-2(3H)-one system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å for the carbonyl C atom. Its mean plane is almost perpendicular to the benzyl plane and to the allyl group, making dihedral angles of 80.6 (1) and 77.4 (3)°, respectively. The benzyl group and the allyl subsituent lie on opposite sides of the fused ring system. In the crystal, mol-ecules are linked by bifurcated C-H⋯O hydrogen bonds in which the carbonyl O atom acts as accepter to two aromatic C-H groups, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994 ▶); Soderlind et al. (1999 ▶); Bouwman et al. (1990 ▶) and for potential applications in the treatment of some diseases, see: Zhu et al. (2008 ▶); Ogino et al. (2008 ▶); Shah et al. (2008 ▶). For their use as inter­mediates in chemical synthesis, see: Bai et al. (2001 ▶). For similar compounds, see: Belaziz et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C17H16N2O

M = 264.32

Triclinic,

a = 9.0667 (2) Å

b = 9.3922 (2) Å

c = 9.6486 (2) Å

α = 94.218 (1)°

β = 113.543 (1)°

γ = 106.265 (1)°

V = 706.87 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.43 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.988

12670 measured reflections

3494 independent reflections

2573 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.141

S = 1.06

3494 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT-Plus; 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 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813023568/im2438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023568/im2438Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023568/im2438Isup3.cml

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

C17H16N2O	Z = 2
Mr = 264.32	F(000) = 280
Triclinic, P1	Dx = 1.242 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0667 (2) Å	Cell parameters from 3494 reflections
b = 9.3922 (2) Å	θ = 2.3–28.3°
c = 9.6486 (2) Å	µ = 0.08 mm−1
α = 94.218 (1)°	T = 296 K
β = 113.543 (1)°	Irregular shape, colourless
γ = 106.265 (1)°	0.43 × 0.20 × 0.16 mm
V = 706.87 (3) Å3

Bruker APEXII CCD diffractometer	3494 independent reflections
Radiation source: microfocus source	2573 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.967, Tmax = 0.988	k = −12→12
12670 measured reflections	l = −12→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.1232P] where P = (Fo2 + 2Fc2)/3
3494 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.08458 (17)	0.53012 (15)	0.75007 (15)	0.0503 (3)
C2	−0.0580 (2)	0.4975 (2)	0.77755 (18)	0.0652 (4)
H2	−0.0800	0.4235	0.8325	0.078*
C3	−0.1663 (2)	0.5780 (2)	0.7211 (2)	0.0785 (5)
H3	−0.2638	0.5575	0.7376	0.094*
C4	−0.1336 (2)	0.6887 (2)	0.6404 (2)	0.0778 (5)
H4	−0.2098	0.7410	0.6034	0.093*
C5	0.0111 (2)	0.72378 (18)	0.61297 (19)	0.0636 (4)
H5	0.0338	0.7989	0.5594	0.076*
C6	0.11833 (17)	0.64210 (14)	0.66878 (15)	0.0484 (3)
C7	0.33127 (18)	0.54248 (15)	0.73733 (17)	0.0524 (3)
C8	0.2415 (2)	0.35712 (18)	0.88407 (19)	0.0710 (5)
H8A	0.2268	0.3845	0.9755	0.085*
H8B	0.3582	0.3588	0.9181	0.085*
C9	0.1241 (3)	0.20112 (19)	0.8030 (2)	0.0777 (5)
H9	0.1257	0.1609	0.7128	0.093*
C10	0.0209 (3)	0.1174 (3)	0.8466 (4)	0.1171 (9)
H10A	0.0154	0.1535	0.9362	0.141*
H10B	−0.0490	0.0201	0.7889	0.141*
C11	0.3572 (2)	0.74859 (15)	0.59174 (18)	0.0576 (4)
H11A	0.2751	0.7508	0.4904	0.069*
H11B	0.4401	0.7099	0.5778	0.069*
C12	0.44798 (18)	0.90823 (15)	0.68814 (16)	0.0507 (3)
C13	0.4105 (2)	1.02876 (17)	0.6275 (2)	0.0635 (4)
H13	0.3285	1.0118	0.5261	0.076*
C14	0.4935 (3)	1.17505 (18)	0.7159 (3)	0.0762 (5)
H14	0.4671	1.2557	0.6738	0.091*
C15	0.6135 (3)	1.2009 (2)	0.8642 (3)	0.0798 (6)
H15	0.6686	1.2991	0.9236	0.096*
C16	0.6534 (3)	1.0830 (2)	0.9259 (2)	0.0854 (6)
H16	0.7360	1.1011	1.0273	0.102*
C17	0.5712 (2)	0.93636 (19)	0.8379 (2)	0.0709 (5)
H17	0.5994	0.8565	0.8803	0.085*
N1	0.21567 (15)	0.47062 (13)	0.79022 (14)	0.0546 (3)
N2	0.26911 (15)	0.64676 (12)	0.66155 (14)	0.0504 (3)
O1	0.46264 (14)	0.51931 (12)	0.75495 (15)	0.0703 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0468 (7)	0.0456 (7)	0.0449 (7)	0.0041 (6)	0.0168 (6)	−0.0037 (5)
C2	0.0565 (9)	0.0695 (10)	0.0581 (9)	0.0033 (7)	0.0286 (7)	−0.0032 (7)
C3	0.0530 (9)	0.0892 (13)	0.0808 (12)	0.0110 (9)	0.0317 (9)	−0.0143 (10)
C4	0.0553 (10)	0.0799 (12)	0.0836 (12)	0.0281 (9)	0.0168 (9)	−0.0067 (10)
C5	0.0600 (9)	0.0563 (9)	0.0633 (9)	0.0209 (7)	0.0168 (7)	0.0043 (7)
C6	0.0462 (7)	0.0418 (6)	0.0467 (7)	0.0087 (5)	0.0164 (6)	−0.0024 (5)
C7	0.0488 (8)	0.0387 (6)	0.0586 (8)	0.0074 (6)	0.0193 (6)	0.0016 (6)
C8	0.0755 (11)	0.0578 (9)	0.0593 (9)	0.0110 (8)	0.0165 (8)	0.0192 (7)
C9	0.0935 (13)	0.0534 (9)	0.0736 (11)	0.0171 (9)	0.0287 (10)	0.0196 (8)
C10	0.120 (2)	0.0697 (13)	0.162 (2)	0.0150 (13)	0.0698 (18)	0.0428 (15)
C11	0.0682 (9)	0.0451 (7)	0.0594 (8)	0.0098 (7)	0.0352 (7)	0.0057 (6)
C12	0.0544 (8)	0.0424 (7)	0.0567 (8)	0.0078 (6)	0.0322 (7)	0.0066 (6)
C13	0.0704 (10)	0.0526 (8)	0.0670 (9)	0.0180 (7)	0.0316 (8)	0.0126 (7)
C14	0.0904 (13)	0.0455 (8)	0.1024 (15)	0.0198 (8)	0.0541 (12)	0.0139 (9)
C15	0.0848 (13)	0.0490 (9)	0.0948 (14)	−0.0039 (8)	0.0512 (11)	−0.0105 (9)
C16	0.0789 (12)	0.0732 (12)	0.0676 (11)	−0.0026 (9)	0.0191 (9)	−0.0043 (9)
C17	0.0726 (11)	0.0556 (9)	0.0693 (10)	0.0109 (8)	0.0237 (9)	0.0128 (8)
N1	0.0539 (7)	0.0447 (6)	0.0559 (7)	0.0095 (5)	0.0199 (5)	0.0109 (5)
N2	0.0508 (6)	0.0381 (5)	0.0604 (7)	0.0103 (5)	0.0262 (5)	0.0074 (5)
O1	0.0533 (6)	0.0580 (6)	0.0960 (9)	0.0210 (5)	0.0287 (6)	0.0116 (6)

C1—C2	1.378 (2)	C9—C10	1.274 (3)
C1—N1	1.3824 (19)	C9—H9	0.9300
C1—C6	1.396 (2)	C10—H10A	0.9300
C2—C3	1.371 (3)	C10—H10B	0.9300
C2—H2	0.9300	C11—N2	1.4503 (18)
C3—C4	1.381 (3)	C11—C12	1.5109 (19)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.396 (3)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.376 (2)
C5—C6	1.373 (2)	C12—C17	1.377 (2)
C5—H5	0.9300	C13—C14	1.385 (2)
C6—N2	1.3853 (18)	C13—H13	0.9300
C7—O1	1.2181 (17)	C14—C15	1.359 (3)
C7—N1	1.3771 (19)	C14—H14	0.9300
C7—N2	1.3773 (18)	C15—C16	1.364 (3)
C8—N1	1.4572 (19)	C15—H15	0.9300
C8—C9	1.478 (2)	C16—C17	1.386 (2)
C8—H8A	0.9700	C16—H16	0.9300
C8—H8B	0.9700	C17—H17	0.9300
C2—C1—N1	131.78 (15)	H10A—C10—H10B	120.0
C2—C1—C6	121.12 (15)	N2—C11—C12	112.61 (11)
N1—C1—C6	107.10 (12)	N2—C11—H11A	109.1
C3—C2—C1	117.73 (17)	C12—C11—H11A	109.1
C3—C2—H2	121.1	N2—C11—H11B	109.1
C1—C2—H2	121.1	C12—C11—H11B	109.1
C2—C3—C4	121.36 (17)	H11A—C11—H11B	107.8
C2—C3—H3	119.3	C13—C12—C17	118.60 (14)
C4—C3—H3	119.3	C13—C12—C11	120.70 (14)
C3—C4—C5	121.50 (17)	C17—C12—C11	120.70 (14)
C3—C4—H4	119.2	C12—C13—C14	120.70 (17)
C5—C4—H4	119.2	C12—C13—H13	119.6
C6—C5—C4	116.84 (17)	C14—C13—H13	119.6
C6—C5—H5	121.6	C15—C14—C13	120.04 (17)
C4—C5—H5	121.6	C15—C14—H14	120.0
C5—C6—N2	131.80 (14)	C13—C14—H14	120.0
C5—C6—C1	121.45 (14)	C14—C15—C16	120.13 (16)
N2—C6—C1	106.75 (12)	C14—C15—H15	119.9
O1—C7—N1	126.96 (14)	C16—C15—H15	119.9
O1—C7—N2	126.92 (14)	C15—C16—C17	120.12 (18)
N1—C7—N2	106.13 (12)	C15—C16—H16	119.9
N1—C8—C9	114.03 (14)	C17—C16—H16	119.9
N1—C8—H8A	108.7	C12—C17—C16	120.40 (17)
C9—C8—H8A	108.7	C12—C17—H17	119.8
N1—C8—H8B	108.7	C16—C17—H17	119.8
C9—C8—H8B	108.7	C7—N1—C1	109.97 (12)
H8A—C8—H8B	107.6	C7—N1—C8	122.70 (14)
C10—C9—C8	125.3 (2)	C1—N1—C8	127.18 (14)
C10—C9—H9	117.4	C7—N2—C6	110.04 (12)
C8—C9—H9	117.4	C7—N2—C11	123.15 (12)
C9—C10—H10A	120.0	C6—N2—C11	126.76 (12)
C9—C10—H10B	120.0
N1—C1—C2—C3	−179.88 (14)	C15—C16—C17—C12	−0.5 (3)
C6—C1—C2—C3	0.6 (2)	O1—C7—N1—C1	178.76 (14)
C1—C2—C3—C4	−0.4 (2)	N2—C7—N1—C1	−0.76 (15)
C2—C3—C4—C5	−0.1 (3)	O1—C7—N1—C8	2.9 (2)
C3—C4—C5—C6	0.6 (2)	N2—C7—N1—C8	−176.64 (12)
C4—C5—C6—N2	179.56 (14)	C2—C1—N1—C7	−179.26 (14)
C4—C5—C6—C1	−0.5 (2)	C6—C1—N1—C7	0.34 (15)
C2—C1—C6—C5	−0.1 (2)	C2—C1—N1—C8	−3.6 (2)
N1—C1—C6—C5	−179.75 (12)	C6—C1—N1—C8	175.99 (13)
C2—C1—C6—N2	179.87 (12)	C9—C8—N1—C7	−109.85 (18)
N1—C1—C6—N2	0.22 (14)	C9—C8—N1—C1	75.0 (2)
N1—C8—C9—C10	−121.4 (2)	O1—C7—N2—C6	−178.62 (14)
N2—C11—C12—C13	−122.16 (15)	N1—C7—N2—C6	0.90 (15)
N2—C11—C12—C17	58.5 (2)	O1—C7—N2—C11	−1.0 (2)
C17—C12—C13—C14	−0.7 (2)	N1—C7—N2—C11	178.55 (11)
C11—C12—C13—C14	179.94 (15)	C5—C6—N2—C7	179.26 (14)
C12—C13—C14—C15	0.0 (3)	C1—C6—N2—C7	−0.70 (14)
C13—C14—C15—C16	0.5 (3)	C5—C6—N2—C11	1.7 (2)
C14—C15—C16—C17	−0.3 (3)	C1—C6—N2—C11	−178.24 (12)
C13—C12—C17—C16	0.9 (3)	C12—C11—N2—C7	−102.99 (15)
C11—C12—C17—C16	−179.72 (16)	C12—C11—N2—C6	74.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.48	3.405 (2)	173
C14—H14···O1ii	0.93	2.56	3.330 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.48	3.405 (2)	173
C14—H14⋯O1ii	0.93	2.56	3.330 (2)	141

Symmetry codes: (i) ; (ii) .