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

The fused five- and six-membered rings in the title compound, C(10)H(10)N(2)O, are approximately coplanar, with an r.m.s. deviation of 0.008 Å. The mean plane of the allyl group is roughly perpendicular to the mean plane of the 1,3-benzimidazol-2(3H)-one system, making a dihedral angle of 86.1 (2)°. In the crystal, each mol-ecule is linked to its symmetry equivalent partner by a pair of N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the pharmacological and biochemical properties of the title compound, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For compounds with similar structures, see: Belaziz et al. (2012 ▶); Ouzidan et al. (2011 ▶).

Experimental

Crystal data

C10H10N2O

M = 174.20

Monoclinic,

a = 10.2749 (5) Å

b = 5.5787 (3) Å

c = 16.6220 (9) Å

β = 100.976 (4)°

V = 935.35 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.38 × 0.29 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

13429 measured reflections

2570 independent reflections

1393 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.04

2570 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536812043620/fj2602sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043620/fj2602Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043620/fj2602Isup3.cml

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

C10H10N2O	F(000) = 368
Mr = 174.20	Dx = 1.237 Mg m−3
Monoclinic, P21/c	Melting point: 342.7 K
Hall symbol: -p 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2749 (5) Å	Cell parameters from 2570 reflections
b = 5.5787 (3) Å	θ = 2.9–29.4°
c = 16.6220 (9) Å	µ = 0.08 mm−1
β = 100.976 (4)°	T = 296 K
V = 935.35 (8) Å3	Block, colourless
Z = 4	0.38 × 0.29 × 0.27 mm

Bruker X8 APEX diffractometer	1393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 29.4°, θmin = 2.9°
φ and ω scans	h = −13→14
13429 measured reflections	k = −7→7
2570 independent reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2570 reflections	Δρmax = 0.14 e Å−3
120 parameters	Δρmin = −0.14 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: 0.011 (4)

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 > 2σ(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	0.64101 (14)	0.3295 (2)	0.87918 (9)	0.0444 (4)
C2	0.63854 (16)	0.3098 (3)	0.79675 (9)	0.0549 (4)
H2A	0.5937	0.1851	0.7662	0.066*
C3	0.70534 (18)	0.4825 (3)	0.76048 (9)	0.0638 (5)
H3	0.7056	0.4732	0.7046	0.077*
C4	0.77162 (19)	0.6684 (3)	0.80584 (10)	0.0651 (5)
H4	0.8153	0.7820	0.7798	0.078*
C5	0.77454 (16)	0.6892 (2)	0.88889 (10)	0.0557 (4)
H5	0.8189	0.8149	0.9191	0.067*
C6	0.70925 (14)	0.5166 (2)	0.92520 (8)	0.0436 (4)
C7	0.74323 (15)	0.6384 (2)	1.07492 (9)	0.0512 (4)
H7A	0.7020	0.5928	1.1205	0.061*
H7B	0.7180	0.8027	1.0605	0.061*
C8	0.88971 (17)	0.6264 (3)	1.10148 (10)	0.0656 (5)
H8	0.9191	0.4602	1.1144	0.105 (7)*
C9	0.9688 (2)	0.8074 (4)	1.11471 (13)	0.0968 (7)
H9A	1.0714	0.7945	1.1346	0.116*
H9B	0.9256	0.9702	1.1048	0.116*
C10	0.61611 (15)	0.2860 (2)	1.01062 (9)	0.0441 (4)
N1	0.69312 (11)	0.48505 (18)	1.00561 (7)	0.0452 (3)
N2	0.58638 (12)	0.19162 (19)	0.93391 (7)	0.0481 (3)
H2	0.5401	0.0640	0.9210	0.058*
O1	0.58255 (11)	0.21105 (17)	1.07330 (6)	0.0559 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0415 (9)	0.0445 (7)	0.0468 (9)	0.0002 (5)	0.0072 (7)	0.0025 (6)
C2	0.0578 (11)	0.0578 (9)	0.0476 (10)	−0.0040 (7)	0.0064 (8)	−0.0033 (6)
C3	0.0733 (13)	0.0750 (11)	0.0442 (9)	−0.0033 (8)	0.0137 (8)	0.0056 (7)
C4	0.0751 (13)	0.0680 (11)	0.0555 (11)	−0.0120 (8)	0.0205 (9)	0.0106 (8)
C5	0.0597 (11)	0.0523 (9)	0.0567 (10)	−0.0101 (7)	0.0149 (8)	0.0027 (6)
C6	0.0417 (9)	0.0443 (7)	0.0451 (8)	0.0006 (6)	0.0091 (6)	0.0028 (5)
C7	0.0556 (11)	0.0511 (8)	0.0483 (9)	−0.0034 (6)	0.0132 (8)	−0.0068 (6)
C8	0.0591 (12)	0.0633 (11)	0.0695 (12)	−0.0024 (8)	0.0001 (9)	−0.0102 (8)
C9	0.0674 (15)	0.0902 (15)	0.130 (2)	−0.0206 (10)	0.0128 (13)	−0.0189 (12)
C10	0.0420 (9)	0.0437 (7)	0.0469 (9)	0.0000 (6)	0.0090 (7)	0.0037 (6)
N1	0.0476 (8)	0.0444 (6)	0.0442 (7)	−0.0063 (5)	0.0106 (6)	−0.0014 (4)
N2	0.0514 (8)	0.0439 (6)	0.0491 (8)	−0.0094 (5)	0.0100 (6)	−0.0008 (5)
O1	0.0631 (8)	0.0575 (6)	0.0491 (7)	−0.0111 (5)	0.0159 (6)	0.0066 (4)

C1—C2	1.370 (2)	C7—N1	1.4487 (17)
C1—N2	1.3890 (17)	C7—C8	1.487 (2)
C1—C6	1.4007 (18)	C7—H7A	0.9700
C2—C3	1.386 (2)	C7—H7B	0.9700
C2—H2A	0.9300	C8—C9	1.288 (2)
C3—C4	1.383 (2)	C8—H8	0.9858
C3—H3	0.9300	C9—H9A	1.0463
C4—C5	1.380 (2)	C9—H9B	1.0104
C4—H4	0.9300	C10—O1	1.2313 (16)
C5—C6	1.3768 (19)	C10—N2	1.3594 (17)
C5—H5	0.9300	C10—N1	1.3751 (17)
C6—N1	1.3890 (16)	N2—H2	0.8600
C2—C1—N2	132.67 (13)	C8—C7—H7A	108.9
C2—C1—C6	121.20 (13)	N1—C7—H7B	108.9
N2—C1—C6	106.13 (12)	C8—C7—H7B	108.9
C1—C2—C3	117.58 (14)	H7A—C7—H7B	107.7
C1—C2—H2A	121.2	C9—C8—C7	125.79 (19)
C3—C2—H2A	121.2	C9—C8—H8	122.9
C4—C3—C2	121.15 (15)	C7—C8—H8	111.0
C4—C3—H3	119.4	C8—C9—H9A	124.4
C2—C3—H3	119.4	C8—C9—H9B	115.7
C5—C4—C3	121.56 (14)	H9A—C9—H9B	119.9
C5—C4—H4	119.2	O1—C10—N2	127.79 (13)
C3—C4—H4	119.2	O1—C10—N1	125.63 (13)
C6—C5—C4	117.39 (14)	N2—C10—N1	106.57 (12)
C6—C5—H5	121.3	C10—N1—C6	109.64 (11)
C4—C5—H5	121.3	C10—N1—C7	123.39 (12)
C5—C6—N1	131.91 (13)	C6—N1—C7	126.93 (11)
C5—C6—C1	121.11 (13)	C10—N2—C1	110.67 (12)
N1—C6—C1	106.97 (11)	C10—N2—H2	124.7
N1—C7—C8	113.31 (12)	C1—N2—H2	124.7
N1—C7—H7A	108.9
N2—C1—C2—C3	−179.87 (15)	N2—C10—N1—C6	1.06 (15)
C6—C1—C2—C3	−0.4 (2)	O1—C10—N1—C7	−1.5 (2)
C1—C2—C3—C4	−0.2 (3)	N2—C10—N1—C7	178.85 (12)
C2—C3—C4—C5	0.3 (3)	C5—C6—N1—C10	178.59 (15)
C3—C4—C5—C6	0.3 (3)	C1—C6—N1—C10	−0.59 (15)
C4—C5—C6—N1	179.99 (14)	C5—C6—N1—C7	0.9 (2)
C4—C5—C6—C1	−0.9 (2)	C1—C6—N1—C7	−178.28 (13)
C2—C1—C6—C5	1.0 (2)	C8—C7—N1—C10	112.16 (16)
N2—C1—C6—C5	−179.39 (13)	C8—C7—N1—C6	−70.44 (18)
C2—C1—C6—N1	−179.73 (12)	O1—C10—N2—C1	179.19 (14)
N2—C1—C6—N1	−0.11 (15)	N1—C10—N2—C1	−1.14 (15)
N1—C7—C8—C9	130.56 (19)	C2—C1—N2—C10	−179.66 (15)
O1—C10—N1—C6	−179.26 (13)	C6—C1—N2—C10	0.79 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.00	2.8274 (14)	161
C3—H3···O1ii	0.93	2.52	3.3080 (19)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.00	2.8274 (14)	161
C3—H3⋯O1ii	0.93	2.52	3.3080 (19)	142

Symmetry codes: (i) ; (ii) .