Quinoxaline-2-carbonitrile.

In the title compound, C(9)H(5)N(3), the quinoxaline ring is essentially planar, with a maximum deviation of 0.012 (1) Å. Short inter-molecular distances between the centroids of the 2,3-dihydro-pyrazine and benzene rings [3.6490 (5) Å] indicate the existence of π⋯π inter-actions. In the crystal packing, the mol-ecules are linked via two pairs of inter-molecular C-H⋯N inter-actions, forming R(2) (2) (8) and R(2) (2) (10) ring motifs; these mol-ecules are further linked into a two-dimensional network parallel to (1 0 2) via another C-H⋯N inter-action.

Related literature

For the synthesis of cyano N-heterocyclic compounds, see: Goswami et al. (2007 ▶, 2009 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H5N3

M = 155.16

Monoclinic,

a = 3.8055 (1) Å

b = 19.0466 (4) Å

c = 10.1845 (2) Å

β = 93.466 (1)°

V = 736.84 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.39 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.966, T max = 0.978

11604 measured reflections

2716 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.08

2716 reflections

129 parameters

All H-atom parameters refined

Δρmax = 0.53 e Å−3

Δρmin = −0.23 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/S1600536809051289/sj2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051289/sj2699Isup2.hkl

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

C9H5N3	F(000) = 320
Mr = 155.16	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4710 reflections
a = 3.8055 (1) Å	θ = 2.9–32.7°
b = 19.0466 (4) Å	µ = 0.09 mm−1
c = 10.1845 (2) Å	T = 100 K
β = 93.466 (1)°	Block, yellow
V = 736.84 (3) Å3	0.39 × 0.28 × 0.25 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2716 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 32.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
Tmin = 0.966, Tmax = 0.978	k = −29→21
11604 measured reflections	l = −15→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0782P)2 + 0.0918P] where P = (Fo2 + 2Fc2)/3
2716 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.23 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.12156 (18)	0.46098 (4)	0.84114 (7)	0.01481 (16)
N2	−0.12366 (19)	0.33470 (4)	0.71846 (8)	0.01659 (17)
N3	−0.2187 (2)	0.57757 (5)	0.60971 (9)	0.0269 (2)
C1	0.1884 (2)	0.39728 (4)	0.89844 (8)	0.01344 (17)
C2	0.3822 (2)	0.39456 (5)	1.02181 (9)	0.01744 (18)
C3	0.4514 (2)	0.33059 (5)	1.07937 (10)	0.02033 (19)
C4	0.3352 (2)	0.26756 (5)	1.01678 (10)	0.0210 (2)
C5	0.1474 (2)	0.26871 (5)	0.89805 (9)	0.01857 (19)
C6	0.0674 (2)	0.33382 (4)	0.83638 (9)	0.01441 (17)
C7	−0.1868 (2)	0.39663 (4)	0.66474 (9)	0.01675 (18)
C8	−0.0633 (2)	0.45941 (4)	0.72702 (8)	0.01496 (17)
C9	−0.1450 (2)	0.52598 (5)	0.66332 (9)	0.01913 (19)
H2	0.471 (4)	0.4375 (7)	1.0662 (14)	0.030 (3)*
H3	0.591 (4)	0.3282 (7)	1.1650 (16)	0.038 (4)*
H4	0.396 (3)	0.2229 (7)	1.0622 (13)	0.028 (3)*
H5	0.057 (4)	0.2262 (7)	0.8533 (14)	0.032 (3)*
H7	−0.328 (4)	0.4008 (7)	0.5793 (14)	0.028 (3)*

	U11	U22	U33	U12	U13	U23
N1	0.0154 (3)	0.0145 (3)	0.0146 (3)	0.0003 (2)	0.0014 (2)	0.0010 (2)
N2	0.0168 (3)	0.0173 (3)	0.0157 (4)	−0.0006 (2)	0.0014 (3)	−0.0016 (3)
N3	0.0328 (4)	0.0235 (4)	0.0241 (5)	0.0028 (3)	−0.0002 (3)	0.0057 (3)
C1	0.0128 (3)	0.0147 (3)	0.0130 (4)	0.0002 (2)	0.0019 (3)	0.0004 (3)
C2	0.0157 (4)	0.0218 (4)	0.0147 (4)	−0.0004 (3)	−0.0002 (3)	0.0005 (3)
C3	0.0164 (4)	0.0275 (4)	0.0170 (4)	0.0019 (3)	0.0003 (3)	0.0055 (3)
C4	0.0176 (4)	0.0208 (4)	0.0248 (5)	0.0030 (3)	0.0042 (3)	0.0088 (3)
C5	0.0179 (4)	0.0147 (4)	0.0235 (5)	0.0007 (3)	0.0036 (3)	0.0029 (3)
C6	0.0131 (3)	0.0152 (3)	0.0151 (4)	0.0000 (2)	0.0027 (3)	0.0000 (3)
C7	0.0164 (4)	0.0195 (4)	0.0142 (4)	−0.0003 (3)	0.0000 (3)	−0.0004 (3)
C8	0.0145 (3)	0.0168 (4)	0.0137 (4)	0.0005 (3)	0.0019 (3)	0.0015 (3)
C9	0.0204 (4)	0.0202 (4)	0.0167 (4)	0.0005 (3)	0.0005 (3)	0.0015 (3)

N1—C8	1.3220 (11)	C3—C4	1.4175 (14)
N1—C1	1.3636 (10)	C3—H3	0.995 (16)
N2—C7	1.3161 (11)	C4—C5	1.3670 (13)
N2—C6	1.3659 (11)	C4—H4	0.988 (13)
N3—C9	1.1506 (12)	C5—C6	1.4150 (11)
C1—C2	1.4190 (12)	C5—H5	0.980 (14)
C1—C6	1.4273 (11)	C7—C8	1.4202 (12)
C2—C3	1.3706 (12)	C7—H7	0.997 (14)
C2—H2	0.985 (14)	C8—C9	1.4495 (12)
C8—N1—C1	115.57 (7)	C4—C5—C6	119.57 (8)
C7—N2—C6	116.78 (7)	C4—C5—H5	123.2 (8)
N1—C1—C2	119.01 (7)	C6—C5—H5	117.2 (8)
N1—C1—C6	121.14 (8)	N2—C6—C5	119.33 (7)
C2—C1—C6	119.85 (7)	N2—C6—C1	121.28 (7)
C3—C2—C1	119.16 (8)	C5—C6—C1	119.38 (8)
C3—C2—H2	119.4 (8)	N2—C7—C8	121.44 (8)
C1—C2—H2	121.5 (8)	N2—C7—H7	120.7 (7)
C2—C3—C4	120.92 (9)	C8—C7—H7	117.9 (7)
C2—C3—H3	119.6 (8)	N1—C8—C7	123.77 (7)
C4—C3—H3	119.4 (8)	N1—C8—C9	117.52 (7)
C5—C4—C3	121.10 (8)	C7—C8—C9	118.71 (8)
C5—C4—H4	121.5 (8)	N3—C9—C8	177.49 (10)
C3—C4—H4	117.4 (8)
C8—N1—C1—C2	−179.34 (7)	C4—C5—C6—C1	0.84 (13)
C8—N1—C1—C6	0.75 (12)	N1—C1—C6—N2	−0.95 (13)
N1—C1—C2—C3	−179.68 (8)	C2—C1—C6—N2	179.14 (7)
C6—C1—C2—C3	0.24 (13)	N1—C1—C6—C5	178.94 (7)
C1—C2—C3—C4	0.62 (13)	C2—C1—C6—C5	−0.97 (12)
C2—C3—C4—C5	−0.75 (14)	C6—N2—C7—C8	−0.32 (13)
C3—C4—C5—C6	0.00 (14)	C1—N1—C8—C7	−0.38 (12)
C7—N2—C6—C5	−179.20 (7)	C1—N1—C8—C9	179.15 (7)
C7—N2—C6—C1	0.69 (12)	N2—C7—C8—N1	0.18 (14)
C4—C5—C6—N2	−179.26 (7)	N2—C7—C8—C9	−179.36 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1i	0.984 (14)	2.619 (14)	3.5730 (12)	163.4 (12)
C4—H4···N2ii	0.988 (13)	2.593 (13)	3.4268 (12)	142.0 (10)
C7—H7···N3iii	0.998 (14)	2.540 (15)	3.5225 (12)	168.3 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1i	0.984 (14)	2.619 (14)	3.5730 (12)	163.4 (12)
C4—H4⋯N2ii	0.988 (13)	2.593 (13)	3.4268 (12)	142.0 (10)
C7—H7⋯N3iii	0.998 (14)	2.540 (15)	3.5225 (12)	168.3 (12)

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