3-(1H-Imidazol-1-yl)propane-nitrile.

The title compound, C(6)H(7)N(3), has an ethyl-ene group connecting an imidazole ring and a -CN group. These groups are in a staggered conformation. The shortest inter-molecular contact is found between the imidazole N atom and a -CH(2)- group of a neighboring mol-ecule.

Related literature

For background and applications of ionic liquids, see: Hayashi et al. (2006 ▶); Kozlova et al. (2009a ▶,b ▶); Lombardo et al. (2007 ▶); Macaev et al. (2007 ▶); Sawa & Okamura (1969 ▶); Scheers et al. (2008 ▶); Visser et al. (2001 ▶); Wang et al. (2003 ▶); Wasserscheid & Keim (2000 ▶); Xu et al. (2007 ▶); Yamauchi & Masui (1976 ▶); Yang et al. (2006 ▶).

Experimental

Crystal data

C6H7N3

M = 121.15

Monoclinic,

a = 7.2712 (3) Å

b = 5.5917 (2) Å

c = 15.4625 (5) Å

β = 100.979 (1)°

V = 617.17 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.45 × 0.40 × 0.30 mm

Data collection

Bruker–Nonius X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.946, T max = 0.975

11604 measured reflections

1542 independent reflections

1456 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.04

1542 reflections

111 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: ct.exe (Köckerling, 1996 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035685/om2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035685/om2269Isup2.hkl

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

C6H7N3	Dx = 1.304 Mg m−3
Mr = 121.15	Melting point: 310 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2712 (3) Å	Cell parameters from 8906 reflections
b = 5.5917 (2) Å	θ = 2.7–28.3°
c = 15.4625 (5) Å	µ = 0.09 mm−1
β = 100.979 (1)°	T = 173 K
V = 617.17 (4) Å3	Block, colourless
Z = 4	0.45 × 0.40 × 0.30 mm
F(000) = 256

Bruker–Nonius X8 Apex diffractometer	1542 independent reflections
Radiation source: fine-focus sealed tube	1456 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 28.3°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.946, Tmax = 0.975	k = −7→7
11604 measured reflections	l = −20→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	All H-atom parameters refined
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.1206P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1542 reflections	Δρmax = 0.27 e Å−3
111 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: 0.064 (15)

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
N1	0.76561 (9)	0.2518 (1)	0.30688 (4)	0.0207 (2)
C1	0.6541 (1)	0.1964 (2)	0.22892 (5)	0.0254 (2)
H1	0.579 (2)	0.053 (2)	0.2217 (7)	0.033 (3)*
N2	0.6623 (1)	0.3580 (1)	0.16800 (4)	0.0302 (2)
C2	0.7866 (1)	0.5266 (2)	0.20919 (6)	0.0281 (2)
H2	0.817 (2)	0.670 (2)	0.1771 (8)	0.037 (3)*
C3	0.8519 (1)	0.4648 (1)	0.29465 (5)	0.0249 (2)
H3	0.944 (2)	0.535 (2)	0.3408 (8)	0.035 (3)*
C4	0.7876 (1)	0.1115 (1)	0.38757 (5)	0.0239 (2)
H4A	0.919 (2)	0.109 (2)	0.4147 (7)	0.030 (3)*
H4B	0.744 (2)	−0.051 (2)	0.3700 (7)	0.031 (3)*
C5	0.6708 (1)	0.2069 (2)	0.45232 (5)	0.0254 (2)
H5A	0.683 (2)	0.100 (2)	0.5022 (8)	0.037 (3)*
H5B	0.538 (2)	0.217 (2)	0.4243 (7)	0.035 (3)*
C6	0.7298 (1)	0.4436 (2)	0.48692 (5)	0.0244 (2)
N3	0.7779 (1)	0.6275 (1)	0.51425 (5)	0.0333 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0242 (3)	0.0212 (3)	0.0176 (3)	0.0012 (2)	0.0061 (2)	0.0007 (2)
C1	0.0293 (4)	0.0279 (4)	0.0194 (4)	0.0001 (3)	0.0057 (3)	−0.0026 (3)
N2	0.0345 (4)	0.0371 (4)	0.0196 (3)	0.0033 (3)	0.0064 (3)	0.0029 (3)
C2	0.0290 (4)	0.0307 (4)	0.0271 (4)	0.0027 (3)	0.0113 (3)	0.0075 (3)
C3	0.0246 (4)	0.0249 (4)	0.0257 (4)	−0.0015 (3)	0.0065 (3)	0.0023 (3)
C4	0.0318 (4)	0.0213 (4)	0.0188 (3)	0.0026 (3)	0.0058 (3)	0.0025 (3)
C5	0.0321 (4)	0.0265 (4)	0.0190 (4)	−0.0056 (3)	0.0084 (3)	−0.0011 (3)
C6	0.0265 (4)	0.0288 (4)	0.0186 (3)	0.0011 (3)	0.0060 (3)	−0.0002 (3)
N3	0.0386 (4)	0.0303 (4)	0.0313 (4)	−0.0002 (3)	0.0078 (3)	−0.0047 (3)

N1—C1	1.354 (1)	C6—N3	1.141 (1)
N1—C3	1.376 (1)	C1—H1	0.97 (1)
N1—C4	1.4565 (9)	C2—H2	0.99 (1)
C1—N2	1.315 (1)	C3—H3	0.97 (1)
N2—C2	1.376 (1)	C4—H4A	0.97 (1)
C2—C3	1.361 (1)	C4—H4B	0.99 (1)
C4—C5	1.527 (1)	C5—H5A	0.97 (1)
C5—C6	1.461 (1)	C5—H5B	0.98 (1)
C1—N1—C3	106.68 (6)	H2—C2—N2	120.9 (7)
C1—N1—C4	126.06 (7)	H3—C3—C2	132.8 (7)
C3—N1—C4	127.27 (7)	H3—C3—N1	121.4 (7)
N2—C1—N1	112.30 (7)	H4A—C4—H4B	110.4 (9)
C1—N2—C2	104.76 (7)	H4A—C4—N1	108.5 (7)
C3—C2—N2	110.64 (7)	H4B—C4—N1	106.5 (7)
C2—C3—N1	105.63 (7)	H4A—C4—C5	110.2 (7)
N1—C4—C5	112.92 (6)	H4B—C4—C5	108.2 (7)
C6—C5—C4	113.28 (7)	H5A—C5—H5B	109 (1)
N3—C6—C5	179.24 (9)	H5A—C5—C6	107.0 (7)
H1—C1—N2	126.2 (7)	H5B—C5—C6	107.9 (7)
H1—C1—N1	121.5 (7)	H5A—C5—C4	109.2 (7)
H2—C2—C3	128.4 (7)	H5B—C5—C4	110.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2i	0.97 (1)	2.66 (1)	3.366 (1)	135.7 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N2i	0.97 (1)	2.66 (1)	3.366 (1)	135.7 (9)

Symmetry code: (i) .