1-Allyl-5-nitro-1H-benzimidazol-2(3H)-one.

The benzimidazolone residue in the title mol-ecule, C10H9N3O3, is almost planar, with the largest deviation from the mean plane being 0.016 (2) Å for the C atom linked to the nitro group. This plane is nearly perpendicular to the 1-allyl chain as indicated by the C-N-C-C torsion angle of 90.9 (3)°. The fused-ring system makes a dihedral angle of 5.6 (3)° with the nitro group, leading to a synperiplanar conformation. In the crystal, zigzag supra-molecular chains are formed along the a axis by N-H⋯O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benz­imid­azoles and derivatives, see: Al Muhaimeed (1997 ▶); Scott et al. (2002 ▶); Nakano et al. (2000 ▶); Zhu et al. (2000 ▶); Zarrinmayeh et al. (1998 ▶). For related structures, see: Ouzidan et al. (2011a ▶,b ▶).

Experimental

Crystal data

C10H9N3O3

M = 219.20

Orthorhombic,

a = 8.3246 (3) Å

b = 14.9567 (6) Å

c = 16.4461 (7) Å

V = 2047.68 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.46 × 0.31 × 0.18 mm

Data collection

Bruker X8 APEXII area-detector diffractometer

12145 measured reflections

1940 independent reflections

1483 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.168

S = 1.05

1940 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.38 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/S1600536813004790/tk5200sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004790/tk5200Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004790/tk5200Isup3.cml

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

C10H9N3O3	F(000) = 912
Mr = 219.20	Dx = 1.422 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1940 reflections
a = 8.3246 (3) Å	θ = 3.0–25.7°
b = 14.9567 (6) Å	µ = 0.11 mm−1
c = 16.4461 (7) Å	T = 296 K
V = 2047.68 (14) Å3	Block, colourless
Z = 8	0.46 × 0.31 × 0.18 mm

Bruker X8 APEXII area-detector diffractometer	1483 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.7°, θmin = 3.0°
φ and ω scans	h = −10→5
12145 measured reflections	k = −17→18
1940 independent reflections	l = −20→17

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0827P)2 + 1.3415P] where P = (Fo2 + 2Fc2)/3
1940 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.38 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
C1	0.1801 (3)	−0.05403 (17)	0.37164 (15)	0.0479 (6)
C2	0.1529 (3)	0.02563 (16)	0.41211 (15)	0.0469 (6)
H2	0.0502	0.0439	0.4269	0.056*
C3	0.2866 (3)	0.07620 (16)	0.42913 (14)	0.0433 (6)
C4	0.4416 (3)	0.04786 (16)	0.40696 (14)	0.0432 (6)
C5	0.4658 (3)	−0.03268 (18)	0.36771 (16)	0.0517 (6)
H5	0.5685	−0.0516	0.3538	0.062*
C6	0.3328 (3)	−0.08415 (18)	0.34984 (16)	0.0532 (6)
H6	0.3449	−0.1387	0.3234	0.064*
C7	0.4612 (3)	0.18307 (17)	0.46777 (15)	0.0470 (6)
C8	0.7198 (3)	0.11726 (18)	0.41762 (15)	0.0505 (6)
H8A	0.7613	0.0567	0.4152	0.061*
H8B	0.7714	0.1474	0.4628	0.061*
C9	0.7608 (4)	0.1651 (3)	0.3401 (2)	0.0817 (10)
H9	0.7305	0.2249	0.3380	0.098*
C10	0.8257 (7)	0.1378 (4)	0.2815 (3)	0.1325 (19)
H10A	0.8593	0.0786	0.2794	0.159*
H10B	0.8434	0.1755	0.2375	0.159*
N1	0.0402 (3)	−0.10842 (16)	0.34996 (15)	0.0589 (6)
N2	0.3035 (2)	0.15796 (14)	0.46649 (13)	0.0506 (6)
H2N	0.2257	0.1889	0.4863	0.061*
N3	0.5459 (2)	0.11428 (13)	0.43179 (12)	0.0455 (5)
O1	0.0603 (3)	−0.17533 (15)	0.30908 (16)	0.0871 (8)
O2	−0.0927 (2)	−0.08426 (14)	0.37286 (15)	0.0746 (7)
O3	0.5177 (2)	0.25247 (13)	0.49549 (13)	0.0607 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0473 (13)	0.0443 (14)	0.0521 (13)	−0.0050 (11)	0.0021 (10)	−0.0018 (11)
C2	0.0375 (12)	0.0459 (14)	0.0573 (14)	0.0000 (10)	0.0064 (10)	−0.0019 (11)
C3	0.0391 (12)	0.0427 (13)	0.0479 (13)	0.0012 (10)	0.0048 (9)	−0.0019 (10)
C4	0.0395 (12)	0.0459 (13)	0.0441 (12)	0.0020 (10)	0.0034 (9)	−0.0012 (10)
C5	0.0453 (13)	0.0507 (15)	0.0592 (15)	0.0083 (11)	0.0064 (11)	−0.0064 (12)
C6	0.0573 (15)	0.0438 (14)	0.0584 (15)	0.0040 (11)	0.0039 (12)	−0.0081 (11)
C7	0.0381 (12)	0.0489 (14)	0.0541 (14)	−0.0002 (10)	0.0035 (10)	−0.0042 (11)
C8	0.0331 (12)	0.0633 (16)	0.0551 (14)	0.0048 (11)	0.0010 (10)	−0.0028 (12)
C9	0.0555 (17)	0.110 (3)	0.080 (2)	0.0014 (18)	0.0127 (16)	0.012 (2)
C10	0.181 (5)	0.122 (4)	0.094 (3)	0.021 (4)	0.050 (3)	0.018 (3)
N1	0.0592 (14)	0.0470 (13)	0.0704 (15)	−0.0068 (10)	0.0009 (11)	−0.0055 (11)
N2	0.0353 (10)	0.0469 (12)	0.0695 (13)	−0.0001 (8)	0.0088 (9)	−0.0147 (10)
N3	0.0332 (10)	0.0492 (12)	0.0542 (12)	−0.0002 (8)	0.0036 (8)	−0.0051 (9)
O1	0.0777 (15)	0.0703 (15)	0.1133 (18)	−0.0149 (11)	0.0075 (13)	−0.0401 (13)
O2	0.0483 (11)	0.0586 (13)	0.1169 (18)	−0.0083 (9)	0.0026 (11)	−0.0109 (11)
O3	0.0435 (9)	0.0561 (11)	0.0825 (13)	−0.0072 (8)	0.0022 (9)	−0.0194 (9)

C1—C2	1.383 (3)	C7—N2	1.365 (3)
C1—C6	1.396 (4)	C7—N3	1.381 (3)
C1—N1	1.465 (3)	C8—N3	1.467 (3)
C2—C3	1.374 (3)	C8—C9	1.501 (4)
C2—H2	0.9300	C8—H8A	0.9700
C3—N2	1.376 (3)	C8—H8B	0.9700
C3—C4	1.407 (3)	C9—C10	1.177 (5)
C4—N3	1.381 (3)	C9—H9	0.9300
C4—C5	1.381 (3)	C10—H10A	0.9300
C5—C6	1.380 (4)	C10—H10B	0.9300
C5—H5	0.9300	N1—O1	1.217 (3)
C6—H6	0.9300	N1—O2	1.223 (3)
C7—O3	1.228 (3)	N2—H2N	0.8600
C2—C1—C6	123.4 (2)	N3—C8—C9	111.9 (2)
C2—C1—N1	117.7 (2)	N3—C8—H8A	109.2
C6—C1—N1	118.8 (2)	C9—C8—H8A	109.2
C3—C2—C1	116.1 (2)	N3—C8—H8B	109.2
C3—C2—H2	122.0	C9—C8—H8B	109.2
C1—C2—H2	122.0	H8A—C8—H8B	107.9
C2—C3—N2	131.5 (2)	C10—C9—C8	129.3 (4)
C2—C3—C4	121.6 (2)	C10—C9—H9	115.3
N2—C3—C4	106.84 (19)	C8—C9—H9	115.3
N3—C4—C5	132.4 (2)	C9—C10—H10A	120.0
N3—C4—C3	106.5 (2)	C9—C10—H10B	120.0
C5—C4—C3	121.2 (2)	H10A—C10—H10B	120.0
C6—C5—C4	118.0 (2)	O1—N1—O2	122.5 (2)
C6—C5—H5	121.0	O1—N1—C1	118.8 (2)
C4—C5—H5	121.0	O2—N1—C1	118.7 (2)
C5—C6—C1	119.7 (2)	C7—N2—C3	110.48 (19)
C5—C6—H6	120.1	C7—N2—H2N	124.8
C1—C6—H6	120.1	C3—N2—H2N	124.8
O3—C7—N2	127.4 (2)	C7—N3—C4	109.99 (19)
O3—C7—N3	126.4 (2)	C7—N3—C8	123.3 (2)
N2—C7—N3	106.2 (2)	C4—N3—C8	126.5 (2)
C6—C1—C2—C3	1.2 (4)	C2—C1—N1—O2	−4.6 (4)
N1—C1—C2—C3	−178.0 (2)	C6—C1—N1—O2	176.2 (3)
C1—C2—C3—N2	178.7 (2)	O3—C7—N2—C3	179.0 (2)
C1—C2—C3—C4	−0.4 (4)	N3—C7—N2—C3	−1.3 (3)
C2—C3—C4—N3	179.1 (2)	C2—C3—N2—C7	−178.3 (3)
N2—C3—C4—N3	−0.2 (3)	C4—C3—N2—C7	0.9 (3)
C2—C3—C4—C5	−0.6 (4)	O3—C7—N3—C4	−179.1 (2)
N2—C3—C4—C5	−179.9 (2)	N2—C7—N3—C4	1.2 (3)
N3—C4—C5—C6	−178.8 (2)	O3—C7—N3—C8	−3.4 (4)
C3—C4—C5—C6	0.9 (4)	N2—C7—N3—C8	176.9 (2)
C4—C5—C6—C1	−0.1 (4)	C5—C4—N3—C7	179.1 (3)
C2—C1—C6—C5	−1.0 (4)	C3—C4—N3—C7	−0.6 (3)
N1—C1—C6—C5	178.2 (2)	C5—C4—N3—C8	3.5 (4)
N3—C8—C9—C10	−117.9 (5)	C3—C4—N3—C8	−176.1 (2)
C2—C1—N1—O1	174.6 (3)	C9—C8—N3—C7	−84.0 (3)
C6—C1—N1—O1	−4.6 (4)	C9—C8—N3—C4	90.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3i	0.86	1.96	2.801 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3i	0.86	1.96	2.801 (3)	164

Symmetry code: (i) .