2-(4,5-Dihydro-1H-imidazol-2-yl)-pyridine.

In the mol-ecule of the title compound, C(8)H(9)N(3), a new imidazoline derivative, the six- and five-membered rings are slightly twisted away from each other, forming a dihedral angle of 7.96 (15)°. In the crystal structure, neighbouring mol-ecules are linked together by inter-molecular N-H⋯N hydrogen bonds into extended one-dimensional chains along the a axis. The pyridine N atom is in close proximity to a carbon-bound H atom of the imidazoline ring, with an H⋯N distance of 2.70 Å, which is slightly shorter than the sum of the van der Waals radii of these atoms (2.75 Å). The crystal structure is further stabilized by inter-molecular C-H⋯π and π-π inter-actions (centroid-to-centroid distance 3.853 Å).

Related literature

For related structures and synthesis, see: Stibrany et al. (2004 ▶); Kia et al. (2008 ▶, 2009a ▶,b ▶). For biological and pharmaceutical applications, see, for example: Blancafort (1978 ▶); Chan (1993 ▶); Vizi (1986 ▶); Li et al. (1996 ▶); Ueno et al. (1995 ▶); Corey & Grogan (1999 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H9N3

M = 147.18

Orthorhombic,

a = 10.0057 (8) Å

b = 7.9828 (7) Å

c = 17.6199 (14) Å

V = 1407.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.48 × 0.46 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.992

10642 measured reflections

1238 independent reflections

869 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.146

S = 1.08

1238 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009131/wn2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009131/wn2314Isup2.hkl

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

C8H9N3	F(000) = 624
Mr = 147.18	Dx = 1.389 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3233 reflections
a = 10.0057 (8) Å	θ = 3.1–30.9°
b = 7.9828 (7) Å	µ = 0.09 mm−1
c = 17.6199 (14) Å	T = 100 K
V = 1407.4 (2) Å3	Plate, colourless
Z = 8	0.48 × 0.46 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	1238 independent reflections
Radiation source: fine-focus sealed tube	869 reflections with I > 2σ(I)
graphite	Rint = 0.094
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.959, Tmax = 0.992	k = −9→9
10642 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0658P)2 + 1.1427P] where P = (Fo2 + 2Fc2)/3
1238 reflections	(Δ/σ)max < 0.001
104 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.4819 (2)	0.2650 (3)	−0.01294 (14)	0.0329 (7)
N2	0.2746 (2)	0.1657 (3)	−0.03211 (12)	0.0232 (6)
N3	0.4811 (2)	0.1456 (3)	0.13473 (12)	0.0225 (6)
C1	0.3126 (3)	0.2543 (4)	−0.10232 (14)	0.0251 (7)
H1	0.2478	0.3446	−0.1137	0.030*
H2	0.3149	0.1757	−0.1457	0.030*
C2	0.4531 (3)	0.3285 (4)	−0.08783 (14)	0.0232 (7)
H3	0.5188	0.2877	−0.1256	0.028*
H4	0.4516	0.4525	−0.0886	0.028*
C3	0.3763 (2)	0.1770 (3)	0.01289 (14)	0.0195 (6)
C4	0.3779 (3)	0.1036 (3)	0.08982 (14)	0.0202 (6)
C5	0.2758 (2)	−0.0035 (3)	0.11365 (15)	0.0213 (6)
H5	0.2050	−0.0326	0.0803	0.026*
C6	0.2797 (3)	−0.0662 (4)	0.18629 (14)	0.0231 (7)
H6	0.2106	−0.1378	0.2040	0.028*
C7	0.3852 (3)	−0.0238 (3)	0.23325 (15)	0.0231 (7)
H7	0.3904	−0.0658	0.2836	0.028*
C8	0.4829 (3)	0.0814 (4)	0.20475 (15)	0.0229 (7)
H8	0.5556	0.1097	0.2369	0.027*
H1N1	0.555 (3)	0.278 (4)	0.0109 (16)	0.036 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0146 (14)	0.0501 (17)	0.0340 (15)	−0.0094 (12)	−0.0053 (12)	0.0105 (12)
N2	0.0147 (13)	0.0261 (13)	0.0289 (12)	0.0008 (10)	−0.0021 (10)	−0.0009 (9)
N3	0.0105 (11)	0.0244 (13)	0.0326 (13)	0.0018 (10)	−0.0013 (10)	−0.0013 (10)
C1	0.0138 (14)	0.0320 (16)	0.0296 (15)	0.0004 (12)	−0.0023 (12)	0.0006 (12)
C2	0.0146 (14)	0.0260 (15)	0.0290 (15)	0.0005 (12)	0.0007 (11)	−0.0008 (11)
C3	0.0118 (14)	0.0173 (14)	0.0292 (15)	0.0027 (11)	0.0018 (11)	−0.0038 (11)
C4	0.0108 (13)	0.0180 (14)	0.0317 (15)	0.0048 (11)	0.0008 (11)	−0.0028 (11)
C5	0.0102 (15)	0.0204 (15)	0.0334 (15)	0.0005 (11)	−0.0010 (11)	−0.0056 (11)
C6	0.0161 (15)	0.0205 (15)	0.0327 (16)	−0.0009 (12)	0.0048 (12)	−0.0017 (11)
C7	0.0204 (15)	0.0203 (14)	0.0287 (15)	0.0029 (12)	0.0023 (12)	0.0001 (11)
C8	0.0148 (15)	0.0259 (15)	0.0278 (15)	0.0007 (12)	−0.0042 (11)	−0.0040 (12)

N1—C3	1.349 (3)	C2—H4	0.9900
N1—C2	1.442 (4)	C3—C4	1.477 (4)
N1—H1N1	0.85 (3)	C4—C5	1.397 (4)
N2—C3	1.293 (3)	C5—C6	1.374 (4)
N2—C1	1.475 (3)	C5—H5	0.9500
N3—C8	1.336 (3)	C6—C7	1.383 (4)
N3—C4	1.343 (3)	C6—H6	0.9500
C1—C2	1.547 (4)	C7—C8	1.383 (4)
C1—H1	0.9900	C7—H7	0.9500
C1—H2	0.9900	C8—H8	0.9500
C2—H3	0.9900
C3—N1—C2	109.6 (2)	N2—C3—C4	122.9 (2)
C3—N1—H1N1	125 (2)	N1—C3—C4	120.5 (2)
C2—N1—H1N1	126 (2)	N3—C4—C5	122.5 (2)
C3—N2—C1	106.1 (2)	N3—C4—C3	116.7 (2)
C8—N3—C4	117.3 (2)	C5—C4—C3	120.7 (2)
N2—C1—C2	106.2 (2)	C6—C5—C4	118.8 (2)
N2—C1—H1	110.5	C6—C5—H5	120.6
C2—C1—H1	110.5	C4—C5—H5	120.6
N2—C1—H2	110.5	C5—C6—C7	119.3 (3)
C2—C1—H2	110.5	C5—C6—H6	120.4
H1—C1—H2	108.7	C7—C6—H6	120.4
N1—C2—C1	101.4 (2)	C8—C7—C6	118.1 (2)
N1—C2—H3	111.5	C8—C7—H7	121.0
C1—C2—H3	111.5	C6—C7—H7	121.0
N1—C2—H4	111.5	N3—C8—C7	124.0 (2)
C1—C2—H4	111.5	N3—C8—H8	118.0
H3—C2—H4	109.3	C7—C8—H8	118.0
N2—C3—N1	116.5 (2)
C3—N2—C1—C2	−3.2 (3)	N1—C3—C4—N3	7.7 (4)
C3—N1—C2—C1	−2.3 (3)	N2—C3—C4—C5	9.5 (4)
N2—C1—C2—N1	3.3 (3)	N1—C3—C4—C5	−172.6 (2)
C1—N2—C3—N1	1.9 (3)	N3—C4—C5—C6	1.2 (4)
C1—N2—C3—C4	179.9 (2)	C3—C4—C5—C6	−178.6 (2)
C2—N1—C3—N2	0.4 (3)	C4—C5—C6—C7	−1.0 (4)
C2—N1—C3—C4	−177.7 (2)	C5—C6—C7—C8	0.3 (4)
C8—N3—C4—C5	−0.5 (4)	C4—N3—C8—C7	−0.4 (4)
C8—N3—C4—C3	179.3 (2)	C6—C7—C8—N3	0.5 (4)
N2—C3—C4—N3	−170.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.85 (3)	2.27 (3)	3.084 (3)	160 (3)
C2—H3···Cg1ii	0.99	2.87	3.611 (3)	133
C6—H6···Cg1iii	0.95	2.84	3.561 (3)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3/C4–C8 (pyridine) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.85 (3)	2.27 (3)	3.084 (3)	160 (3)
C2—H3⋯Cg1ii	0.99	2.87	3.611 (3)	133
C6—H6⋯Cg1iii	0.95	2.84	3.561 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) .