1-Prop-2-ynyl-1H-benzimidazol-2-amine.

In the title compound, C(10)H(9)N(3), the benzimidazol-2-amine and CH(2)-C CH units are not coplanar, with a dihedral angle of 60.36° between their mean planes. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonding and π-π inter-actions [centroid-centroid distances 3.677 (1) and 3.580 (1) Å], assembling the mol-ecules into a supra-molecular structure with a three-dimensional network.

Related literature

For the biological activities of benzimidazoles, see: n class="Chemical">Nawrocka et al. (1999 ▶); Cuberens & Contijoch (1997 ▶); Mor et al. (2004 ▶); de Dios et al. (2005 ▶). For polyfunctionality and anti­viral activity of 2-amino­benzimidazoles, see: Garuti & Roberti (2002 ▶); Andries et al. (2003 ▶). For anti­proliferative properties, see: Garuti et al. (1998 ▶); Nawrocka et al. (2005 ▶). For inhibition activity against various strains of bacteria, fungi and yeasts, see: Nofal et al. (2002 ▶); Omar et al. (1996 ▶); Del Poenta et al. (1999 ▶). For structural analysis of small mol­ecules, see: Singh, Agarwal, Mahawar & Awasthi (2011 ▶); Singh, Singh et al. (2011 ▶); Singh, Agarwal & Awasthi (2011 ▶); Agarwal et al. (2011 ▶). For the synthesis, see: Lilienkampf et al. (2009 ▶).

Experimental

Crystal data

C10H9N3

M = 171.20

Monoclinic,

a = 15.385 (2) Å

b = 12.1433 (12) Å

c = 9.4653 (10) Å

β = 95.755 (11)°

V = 1759.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.39 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.677, T max = 1.000

9853 measured reflections

3178 independent reflections

2505 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.137

S = 1.08

3178 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042772/zj2027sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042772/zj2027Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042772/zj2027Isup3.cml

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

C10H9N3	F(000) = 720.0
Mr = 171.20	Dx = 1.293 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2285 reflections
a = 15.385 (2) Å	θ = 3.3–29.2°
b = 12.1433 (12) Å	µ = 0.08 mm−1
c = 9.4653 (10) Å	T = 293 K
β = 95.755 (11)°	Block, clear white
V = 1759.5 (3) Å3	0.39 × 0.36 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3178 independent reflections
Radiation source: fine-focus sealed tube	2505 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 32.5°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −19→23
Tmin = 0.677, Tmax = 1.000	k = −18→18
9853 measured reflections	l = −13→14

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.678P] where P = (Fo2 + 2Fc2)/3
3178 reflections	(Δ/σ)max = 0.006
126 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.18 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
H2N3	0.4017 (11)	−0.0261 (14)	0.750 (2)	0.056 (5)*
H1N3	0.4441 (14)	−0.0599 (17)	0.892 (2)	0.082 (6)*
N2	0.35287 (7)	0.16350 (8)	0.82062 (9)	0.0344 (2)
N1	0.40855 (7)	0.10067 (8)	1.03481 (10)	0.0370 (2)
C5	0.38413 (7)	0.21017 (9)	1.04715 (11)	0.0327 (2)
C7	0.38975 (8)	0.07726 (9)	0.89807 (11)	0.0347 (2)
N3	0.40152 (10)	−0.02285 (9)	0.84084 (12)	0.0507 (3)
C6	0.34953 (7)	0.25096 (9)	0.91465 (11)	0.0332 (2)
C4	0.39113 (9)	0.27854 (11)	1.16533 (13)	0.0416 (3)
H4	0.4128	0.2525	1.2544	0.050*
C9	0.38623 (9)	0.24521 (11)	0.60031 (12)	0.0446 (3)
C3	0.36468 (10)	0.38702 (11)	1.14576 (15)	0.0495 (3)
H3	0.3700	0.4350	1.2227	0.059*
C8	0.32884 (9)	0.16969 (11)	0.66794 (12)	0.0448 (3)
H8A	0.2689	0.1947	0.6500	0.054*
H8B	0.3326	0.0969	0.6268	0.054*
C1	0.32143 (9)	0.35828 (10)	0.89445 (15)	0.0439 (3)
H1	0.2979	0.3839	0.8062	0.053*
C2	0.33019 (10)	0.42580 (10)	1.01311 (17)	0.0508 (3)
H2	0.3126	0.4989	1.0040	0.061*
C10	0.43272 (11)	0.30823 (14)	0.55223 (17)	0.0580 (4)
H10	0.4697	0.3583	0.5140	0.070*

	U11	U22	U33	U12	U13	U23
N2	0.0425 (5)	0.0342 (5)	0.0259 (4)	0.0015 (4)	0.0010 (3)	0.0029 (3)
N1	0.0490 (6)	0.0362 (5)	0.0257 (4)	0.0108 (4)	0.0030 (4)	0.0004 (3)
C5	0.0345 (5)	0.0338 (5)	0.0301 (5)	0.0030 (4)	0.0054 (4)	0.0003 (4)
C7	0.0417 (6)	0.0349 (5)	0.0277 (5)	0.0055 (4)	0.0048 (4)	0.0016 (4)
N3	0.0769 (9)	0.0425 (6)	0.0319 (5)	0.0186 (6)	0.0013 (5)	−0.0051 (4)
C6	0.0347 (5)	0.0322 (5)	0.0331 (5)	−0.0005 (4)	0.0051 (4)	0.0026 (4)
C4	0.0477 (7)	0.0439 (6)	0.0336 (5)	0.0033 (5)	0.0055 (5)	−0.0059 (5)
C9	0.0586 (8)	0.0469 (7)	0.0289 (5)	0.0108 (6)	0.0069 (5)	0.0047 (5)
C3	0.0562 (8)	0.0403 (6)	0.0534 (8)	0.0005 (5)	0.0118 (6)	−0.0139 (6)
C8	0.0554 (8)	0.0482 (7)	0.0289 (5)	−0.0018 (6)	−0.0051 (5)	0.0047 (5)
C1	0.0481 (7)	0.0341 (5)	0.0491 (7)	0.0021 (5)	0.0029 (5)	0.0077 (5)
C2	0.0554 (8)	0.0308 (5)	0.0669 (9)	0.0035 (5)	0.0099 (7)	−0.0020 (6)
C10	0.0669 (10)	0.0587 (8)	0.0513 (8)	0.0076 (7)	0.0205 (7)	0.0105 (7)

N2—C7	1.3684 (14)	C4—H4	0.9300
N2—C6	1.3899 (14)	C9—C10	1.170 (2)
N2—C8	1.4573 (14)	C9—C8	1.4641 (19)
N1—C7	1.3284 (14)	C3—C2	1.395 (2)
N1—C5	1.3898 (14)	C3—H3	0.9300
C5—C4	1.3885 (16)	C8—H8A	0.9700
C5—C6	1.4028 (15)	C8—H8B	0.9700
C7—N3	1.3505 (15)	C1—C2	1.386 (2)
N3—H2N3	0.860 (18)	C1—H1	0.9300
N3—H1N3	0.90 (2)	C2—H2	0.9300
C6—C1	1.3803 (16)	C10—H10	0.9300
C4—C3	1.3856 (19)
C7—N2—C6	106.36 (9)	C5—C4—H4	121.2
C7—N2—C8	128.39 (10)	C10—C9—C8	176.81 (15)
C6—N2—C8	125.00 (10)	C4—C3—C2	121.42 (12)
C7—N1—C5	104.62 (9)	C4—C3—H3	119.3
C4—C5—N1	129.79 (11)	C2—C3—H3	119.3
C4—C5—C6	120.06 (10)	N2—C8—C9	111.21 (11)
N1—C5—C6	110.13 (9)	N2—C8—H8A	109.4
N1—C7—N3	123.96 (11)	C9—C8—H8A	109.4
N1—C7—N2	113.34 (10)	N2—C8—H8B	109.4
N3—C7—N2	122.63 (10)	C9—C8—H8B	109.4
C7—N3—H2N3	117.1 (11)	H8A—C8—H8B	108.0
C7—N3—H1N3	110.8 (13)	C6—C1—C2	116.27 (12)
H2N3—N3—H1N3	116.2 (17)	C6—C1—H1	121.9
C1—C6—N2	131.60 (11)	C2—C1—H1	121.9
C1—C6—C5	122.87 (11)	C1—C2—C3	121.79 (12)
N2—C6—C5	105.52 (9)	C1—C2—H2	119.1
C3—C4—C5	117.57 (12)	C3—C2—H2	119.1
C3—C4—H4	121.2	C9—C10—H10	180.0
C7—N1—C5—C4	−178.09 (12)	N1—C5—C6—C1	−178.69 (11)
C7—N1—C5—C6	0.59 (13)	C4—C5—C6—N2	179.14 (10)
C5—N1—C7—N3	−178.29 (13)	N1—C5—C6—N2	0.31 (12)
C5—N1—C7—N2	−1.34 (14)	N1—C5—C4—C3	177.22 (12)
C6—N2—C7—N1	1.56 (14)	C6—C5—C4—C3	−1.35 (18)
C8—N2—C7—N1	176.05 (11)	C5—C4—C3—C2	1.6 (2)
C6—N2—C7—N3	178.56 (12)	C7—N2—C8—C9	−110.26 (14)
C8—N2—C7—N3	−7.0 (2)	C6—N2—C8—C9	63.27 (15)
C7—N2—C6—C1	177.81 (13)	C10—C9—C8—N2	−27 (3)
C8—N2—C6—C1	3.1 (2)	N2—C6—C1—C2	−177.87 (12)
C7—N2—C6—C5	−1.07 (12)	C5—C6—C1—C2	0.85 (18)
C8—N2—C6—C5	−175.79 (11)	C6—C1—C2—C3	−0.6 (2)
C4—C5—C6—C1	0.14 (18)	C4—C3—C2—C1	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N1i	0.90 (2)	2.36 (2)	3.1823 (18)	153.5 (18)
N3—H2N3···N1ii	0.860 (18)	2.241 (19)	3.0591 (15)	158.6 (15)(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N1i	0.90 (2)	2.36 (2)	3.1823 (18)	153.5 (18)
N3—H2N3⋯N1ii	0.860 (18)	2.241 (19)	3.0591 (15)	158.6 (15)

Symmetry codes: (i) ; (ii) .