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

In the title N-substituted benzimidazol-2-one, C(10)H(10)N(2)O, the fused ring system is almost planar (r.m.s. deviation = 0.01 Å) and aligned at 57.9 (1)° with respect to the propenyl fragment. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into inversion dimers.

Related literature

For the transformation of 1-isopropenyl-1,3-benzimidazol-2-one to other biologically-active compounds, see: Lakhrissi et al. (2010 ▶); Li et al. (2010 ▶). A shorter heating time in the synthesis leads to the formation of 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one; see: Saber et al. (2010 ▶).

Experimental

Crystal data

C10H10N2O

M = 174.20

Monoclinic,

a = 15.8724 (2) Å

b = 6.0971 (1) Å

c = 17.9313 (3) Å

β = 90.961 (2)°

V = 1735.07 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.30 × 0.18 mm

Data collection

Bruker X8 APEXII diffractometer

13930 measured reflections

2506 independent reflections

2231 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 0.98

2506 reflections

123 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017897/nc2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017897/nc2184Isup2.hkl

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

C10H10N2O	F(000) = 736
Mr = 174.20	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8296 reflections
a = 15.8724 (2) Å	θ = 2.3–35.0°
b = 6.0971 (1) Å	µ = 0.09 mm−1
c = 17.9313 (3) Å	T = 100 K
β = 90.961 (2)°	Block, colorless
V = 1735.07 (5) Å3	0.35 × 0.30 × 0.18 mm
Z = 8

Bruker X8 APEXII diffractometer	2231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 30.0°, θmin = 3.4°
φ and ω scans	h = −21→21
13930 measured reflections	k = −8→8
2506 independent reflections	l = −25→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0716P)2 + 0.9009P] where P = (Fo2 + 2Fc2)/3
2506 reflections	(Δ/σ)max = 0.001
123 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.58630 (4)	0.41270 (11)	0.43646 (4)	0.02815 (17)
N1	0.45280 (5)	0.26700 (13)	0.45678 (4)	0.02451 (18)
H1	0.4355 (10)	0.366 (2)	0.4880 (7)	0.048 (4)*
N2	0.53743 (5)	0.08911 (12)	0.38109 (4)	0.02211 (17)
C1	0.40921 (5)	0.08279 (14)	0.43226 (5)	0.02174 (18)
C2	0.32851 (6)	0.00950 (17)	0.44634 (5)	0.0275 (2)
H2	0.2922	0.0883	0.4783	0.033*
C3	0.30248 (6)	−0.18432 (17)	0.41176 (6)	0.0296 (2)
H3	0.2473	−0.2386	0.4201	0.036*
C4	0.35602 (6)	−0.29936 (17)	0.36524 (6)	0.0296 (2)
H4	0.3367	−0.4314	0.3426	0.035*
C5	0.43747 (6)	−0.22577 (15)	0.35092 (5)	0.0259 (2)
H5	0.4740	−0.3051	0.3193	0.031*
C6	0.46266 (5)	−0.03240 (14)	0.38485 (4)	0.02048 (18)
C7	0.53105 (6)	0.27304 (14)	0.42624 (5)	0.02226 (18)
C8	0.60775 (5)	0.04385 (15)	0.33453 (5)	0.02371 (19)
C9	0.64627 (6)	−0.14799 (17)	0.33983 (6)	0.0338 (2)
H9A	0.6272	−0.2545	0.3743	0.041*
H9B	0.6930	−0.1793	0.3091	0.041*
C10	0.62872 (7)	0.21916 (17)	0.27950 (6)	0.0327 (2)
H10A	0.6743	0.1682	0.2476	0.049*
H10B	0.6469	0.3517	0.3062	0.049*
H10C	0.5788	0.2524	0.2487	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0268 (3)	0.0240 (3)	0.0338 (4)	−0.0062 (2)	0.0053 (3)	−0.0065 (3)
N1	0.0231 (4)	0.0223 (4)	0.0284 (4)	−0.0013 (3)	0.0057 (3)	−0.0049 (3)
N2	0.0214 (4)	0.0209 (3)	0.0242 (3)	−0.0038 (3)	0.0054 (3)	−0.0036 (3)
C1	0.0218 (4)	0.0219 (4)	0.0216 (4)	−0.0003 (3)	0.0012 (3)	0.0005 (3)
C2	0.0215 (4)	0.0315 (5)	0.0298 (4)	−0.0009 (3)	0.0044 (3)	−0.0010 (3)
C3	0.0222 (4)	0.0350 (5)	0.0316 (5)	−0.0075 (3)	0.0017 (3)	0.0001 (4)
C4	0.0282 (5)	0.0304 (5)	0.0302 (4)	−0.0090 (4)	0.0004 (3)	−0.0036 (4)
C5	0.0265 (4)	0.0258 (4)	0.0255 (4)	−0.0044 (3)	0.0034 (3)	−0.0044 (3)
C6	0.0199 (4)	0.0216 (4)	0.0200 (4)	−0.0022 (3)	0.0016 (3)	0.0008 (3)
C7	0.0234 (4)	0.0204 (4)	0.0230 (4)	−0.0008 (3)	0.0027 (3)	−0.0013 (3)
C8	0.0215 (4)	0.0263 (4)	0.0235 (4)	−0.0056 (3)	0.0057 (3)	−0.0045 (3)
C9	0.0292 (5)	0.0292 (5)	0.0433 (6)	−0.0002 (4)	0.0114 (4)	−0.0055 (4)
C10	0.0352 (5)	0.0346 (5)	0.0287 (5)	−0.0088 (4)	0.0090 (4)	0.0014 (4)

O1—C7	1.2338 (11)	C3—H3	0.9500
N1—C7	1.3663 (11)	C4—C5	1.3963 (13)
N1—C1	1.3868 (11)	C4—H4	0.9500
N1—H1	0.871 (9)	C5—C6	1.3827 (12)
N2—C7	1.3878 (11)	C5—H5	0.9500
N2—C6	1.4016 (10)	C8—C9	1.3225 (14)
N2—C8	1.4319 (11)	C8—C10	1.4960 (13)
C1—C2	1.3839 (12)	C9—H9A	0.9500
C1—C6	1.3999 (11)	C9—H9B	0.9500
C2—C3	1.3939 (14)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C3—C4	1.3907 (14)	C10—H10C	0.9800
C7—N1—C1	110.29 (7)	C4—C5—H5	121.5
C7—N1—H1	122.5 (11)	C5—C6—C1	121.42 (8)
C1—N1—H1	127.2 (11)	C5—C6—N2	131.94 (8)
C7—N2—C6	109.21 (7)	C1—C6—N2	106.63 (7)
C7—N2—C8	124.13 (7)	O1—C7—N1	127.42 (8)
C6—N2—C8	126.52 (7)	O1—C7—N2	125.86 (8)
C2—C1—N1	131.46 (8)	N1—C7—N2	106.72 (7)
C2—C1—C6	121.39 (8)	C9—C8—N2	119.50 (8)
N1—C1—C6	107.14 (7)	C9—C8—C10	124.87 (9)
C1—C2—C3	117.45 (9)	N2—C8—C10	115.54 (8)
C1—C2—H2	121.3	C8—C9—H9A	120.0
C3—C2—H2	121.3	C8—C9—H9B	120.0
C4—C3—C2	120.99 (9)	H9A—C9—H9B	120.0
C4—C3—H3	119.5	C8—C10—H10A	109.5
C2—C3—H3	119.5	C8—C10—H10B	109.5
C3—C4—C5	121.69 (9)	H10A—C10—H10B	109.5
C3—C4—H4	119.2	C8—C10—H10C	109.5
C5—C4—H4	119.2	H10A—C10—H10C	109.5
C6—C5—C4	117.05 (9)	H10B—C10—H10C	109.5
C6—C5—H5	121.5
C7—N1—C1—C2	−178.46 (10)	C8—N2—C6—C5	4.24 (15)
C7—N1—C1—C6	0.49 (10)	C7—N2—C6—C1	1.11 (10)
N1—C1—C2—C3	179.14 (9)	C8—N2—C6—C1	−174.64 (8)
C6—C1—C2—C3	0.31 (14)	C1—N1—C7—O1	−179.45 (9)
C1—C2—C3—C4	0.29 (15)	C1—N1—C7—N2	0.19 (10)
C2—C3—C4—C5	−0.32 (16)	C6—N2—C7—O1	178.83 (9)
C3—C4—C5—C6	−0.25 (15)	C8—N2—C7—O1	−5.29 (15)
C4—C5—C6—C1	0.85 (13)	C6—N2—C7—N1	−0.81 (10)
C4—C5—C6—N2	−177.89 (9)	C8—N2—C7—N1	175.06 (8)
C2—C1—C6—C5	−0.91 (13)	C7—N2—C8—C9	127.09 (10)
N1—C1—C6—C5	−179.99 (8)	C6—N2—C8—C9	−57.76 (13)
C2—C1—C6—N2	178.11 (8)	C7—N2—C8—C10	−56.22 (12)
N1—C1—C6—N2	−0.97 (9)	C6—N2—C8—C10	118.93 (9)
C7—N2—C6—C5	179.99 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (1)	1.95 (1)	2.811 (1)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (1)	1.95 (1)	2.811 (1)	172 (2)

Symmetry code: (i) .