1-(Prop-2-yn-yl)-1H-benzimidazol-2(3H)-one.

The benzimidazolone part of the title mol-ecule, C10H8N2O, is almost planar [r.m.s. deviation = 0.014 (1) Å] and the NCH2C CH group forms a dihedral angle of 67.95 (6)° with its best plane. In the crystal, mol-ecules form inversion dimers via pairs of N-H⋯O hydrogen bonds. C-H⋯O inter-actions connect the dimers, forming a two-dimensional polymeric network parallel to (100).

Related literature

For pharmacological and biochemical properties of benzimidazole dirivatives, see: Gravatt et al. (1994 ▶); Horton et al. (2003 ▶); Kim et al. (1996 ▶); Roth et al. (1997 ▶). For similar structures, see: Ouzidan, Kandri Rodi, Butcheret al. (2011 ▶); Ouzidan, Kandri Rodi, Fronczek et al. (2011 ▶); Ouzidan, Kandri Rodi, Jasinski et al. (2011 ▶); Belaziz et al. (2012 ▶).

Experimental

Crystal data

C10H8N2O

M = 172.18

Monoclinic,

a = 4.5553 (6) Å

b = 18.001 (3) Å

c = 10.7488 (13) Å

β = 93.645 (8)°

V = 879.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.41 × 0.32 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer

10826 measured reflections

2080 independent reflections

1753 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.05

2080 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 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/S160053681205088X/gk2546sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205088X/gk2546Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205088X/gk2546Isup3.cml

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

C10H8N2O	F(000) = 360
Mr = 172.18	Dx = 1.300 Mg m−3
Monoclinic, P21/c	Melting point: 399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.5553 (6) Å	Cell parameters from 2080 reflections
b = 18.001 (3) Å	θ = 3.0–27.9°
c = 10.7488 (13) Å	µ = 0.09 mm−1
β = 93.645 (8)°	T = 296 K
V = 879.6 (2) Å3	Block, colourless
Z = 4	0.41 × 0.32 × 0.15 mm

Bruker X8 APEXII diffractometer	1753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 27.9°, θmin = 3.0°
φ and ω scans	h = −5→5
10826 measured reflections	k = −23→23
2080 independent reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1197P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2080 reflections	Δρmax = 0.16 e Å−3
119 parameters	Δρmin = −0.16 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: 0.018 (4)

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	0.43254 (19)	0.40104 (4)	0.43888 (7)	0.0527 (2)
N1	0.25564 (19)	0.46700 (5)	0.60486 (8)	0.0425 (2)
H1	0.3557	0.5125	0.5955	0.051*
N2	0.0986 (2)	0.35310 (5)	0.57304 (8)	0.0436 (2)
C1	0.2795 (2)	0.40708 (5)	0.52935 (9)	0.0412 (2)
C2	0.0662 (2)	0.45135 (6)	0.69742 (9)	0.0412 (2)
C3	−0.0238 (3)	0.49315 (7)	0.79538 (11)	0.0523 (3)
H3	0.0420	0.5416	0.8087	0.063*
C4	−0.2163 (3)	0.46000 (9)	0.87330 (12)	0.0623 (4)
H4	−0.2806	0.4868	0.9403	0.075*
C5	−0.3150 (3)	0.38814 (9)	0.85397 (12)	0.0625 (4)
H5	−0.4446	0.3677	0.9080	0.075*
C6	−0.2248 (3)	0.34587 (7)	0.75573 (11)	0.0543 (3)
H6	−0.2904	0.2974	0.7427	0.065*
C7	−0.0329 (2)	0.37902 (6)	0.67788 (9)	0.0421 (3)
C8	0.0605 (3)	0.27990 (6)	0.51808 (11)	0.0539 (3)
H8A	0.1497	0.2789	0.4385	0.065*
H8B	−0.1478	0.2697	0.5029	0.065*
C9	0.1941 (3)	0.22211 (6)	0.59936 (12)	0.0553 (3)
C10	0.2989 (4)	0.17785 (7)	0.66881 (15)	0.0737 (4)
H10	0.3795	0.1424	0.7281	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0709 (5)	0.0453 (4)	0.0429 (4)	−0.0091 (4)	0.0121 (4)	−0.0023 (3)
N1	0.0500 (5)	0.0341 (4)	0.0435 (5)	−0.0036 (3)	0.0030 (4)	0.0009 (3)
N2	0.0516 (5)	0.0355 (4)	0.0434 (5)	−0.0065 (4)	0.0002 (4)	0.0010 (3)
C1	0.0490 (6)	0.0359 (5)	0.0381 (5)	−0.0023 (4)	−0.0020 (4)	0.0038 (4)
C2	0.0389 (5)	0.0424 (5)	0.0415 (5)	0.0029 (4)	−0.0029 (4)	0.0030 (4)
C3	0.0491 (6)	0.0549 (7)	0.0525 (6)	0.0059 (5)	0.0004 (5)	−0.0075 (5)
C4	0.0502 (7)	0.0862 (10)	0.0506 (7)	0.0099 (6)	0.0061 (5)	−0.0070 (6)
C5	0.0464 (6)	0.0881 (10)	0.0536 (7)	−0.0025 (6)	0.0081 (5)	0.0120 (6)
C6	0.0478 (6)	0.0594 (7)	0.0555 (7)	−0.0086 (5)	0.0009 (5)	0.0114 (5)
C7	0.0401 (5)	0.0444 (6)	0.0411 (5)	−0.0010 (4)	−0.0038 (4)	0.0049 (4)
C8	0.0690 (8)	0.0412 (6)	0.0505 (6)	−0.0135 (5)	−0.0032 (5)	−0.0032 (5)
C9	0.0709 (8)	0.0365 (6)	0.0590 (7)	−0.0124 (5)	0.0083 (6)	−0.0038 (5)
C10	0.0977 (11)	0.0425 (7)	0.0799 (10)	−0.0040 (7)	−0.0020 (8)	0.0087 (6)

N1—C1	1.3583 (13)	C8—H8A	0.9700
N1—C2	1.3869 (13)	C8—H8B	0.9700
N1—H1	0.9458	C9—C10	1.1725 (19)
N2—C1	1.3760 (13)	C3—C4	1.3856 (18)
N2—C7	1.3900 (14)	C3—H3	0.9300
N2—C8	1.4500 (13)	C6—C5	1.3848 (19)
C2—C3	1.3775 (15)	C6—H6	0.9300
C2—C7	1.3894 (15)	C5—C4	1.381 (2)
O1—C1	1.2367 (13)	C5—H5	0.9300
C7—C6	1.3835 (15)	C4—H4	0.9300
C8—C9	1.4657 (17)	C10—H10	0.9580
C1—N1—C2	110.15 (9)	N2—C8—H8B	109.3
C1—N1—H1	124.5	C9—C8—H8B	109.3
C2—N1—H1	125.3	H8A—C8—H8B	108.0
C1—N2—C7	109.75 (9)	C10—C9—C8	177.04 (14)
C1—N2—C8	124.15 (9)	C2—C3—C4	117.20 (12)
C7—N2—C8	126.08 (9)	C2—C3—H3	121.4
C3—C2—N1	131.78 (10)	C4—C3—H3	121.4
C3—C2—C7	121.20 (10)	C7—C6—C5	116.98 (12)
N1—C2—C7	107.02 (9)	C7—C6—H6	121.5
C6—C7—C2	121.62 (10)	C5—C6—H6	121.5
C6—C7—N2	131.84 (10)	C4—C5—C6	121.32 (12)
C2—C7—N2	106.54 (9)	C4—C5—H5	119.3
O1—C1—N1	127.61 (9)	C6—C5—H5	119.3
O1—C1—N2	125.87 (9)	C5—C4—C3	121.67 (12)
N1—C1—N2	106.52 (9)	C5—C4—H4	119.2
N2—C8—C9	111.58 (9)	C3—C4—H4	119.2
N2—C8—H8A	109.3	C9—C10—H10	177.7
C9—C8—H8A	109.3
C1—N1—C2—C3	178.95 (11)	C8—N2—C1—O1	−0.04 (17)
C1—N1—C2—C7	−0.44 (11)	C7—N2—C1—N1	−1.39 (11)
C3—C2—C7—C6	−0.13 (16)	C8—N2—C1—N1	−179.94 (9)
N1—C2—C7—C6	179.33 (9)	C1—N2—C8—C9	109.99 (12)
C3—C2—C7—N2	−179.88 (9)	C7—N2—C8—C9	−68.32 (15)
N1—C2—C7—N2	−0.42 (11)	N1—C2—C3—C4	−179.25 (10)
C1—N2—C7—C6	−178.59 (11)	C7—C2—C3—C4	0.07 (16)
C8—N2—C7—C6	−0.07 (18)	C2—C7—C6—C5	0.22 (16)
C1—N2—C7—C2	1.13 (11)	N2—C7—C6—C5	179.90 (11)
C8—N2—C7—C2	179.65 (10)	C7—C6—C5—C4	−0.25 (18)
C2—N1—C1—O1	−178.79 (10)	C6—C5—C4—C3	0.2 (2)
C2—N1—C1—N2	1.12 (11)	C2—C3—C4—C5	−0.10 (18)
C7—N2—C1—O1	178.52 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.95	1.88	2.8226 (12)	174
C10—H10···O1ii	0.96	2.39	3.2541 (17)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.95	1.88	2.8226 (12)	174
C10—H10⋯O1ii	0.96	2.39	3.2541 (17)	149

Symmetry codes: (i) ; (ii) .