Quinoline-2-carbonitrile.

In the title compound, C(10)H(6)N(2), the mol-ecule is almost planar, with an r.m.s. deviation of 0.014 Å. The dihedral angle between the aromatic rings is 1.28 (16)°. In the crystal, mol-ecules are stacked along the a axis by way of weak aromatic π-π stacking inter-actions between the benzene and pyridine rings of adjacent mol-ecules [centroid-centroid separation = 3.7943 (19) Å].

Related literature

For the biological activity and syntheses of quinoline derivatives, see: Sasaki et al. (1998 ▶); Reux et al. (2009 ▶). For related structures, see: Fun et al. (2010 ▶); Loh et al. (2009 ▶, 2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H6N2

M = 154.17

Orthorhombic,

a = 3.8497 (2) Å

b = 9.9559 (4) Å

c = 19.9639 (13) Å

V = 765.16 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.36 × 0.18 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.997

4086 measured reflections

1056 independent reflections

838 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.141

S = 1.09

1056 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810033118/hb5597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033118/hb5597Isup2.hkl

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

C10H6N2	F(000) = 320
Mr = 154.17	Dx = 1.338 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 930 reflections
a = 3.8497 (2) Å	θ = 3.7–27.4°
b = 9.9559 (4) Å	µ = 0.08 mm−1
c = 19.9639 (13) Å	T = 100 K
V = 765.16 (7) Å3	Plate, colourless
Z = 4	0.36 × 0.18 × 0.03 mm

Bruker SMART APEXII CCD diffractometer	1056 independent reflections
Radiation source: fine-focus sealed tube	838 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→4
Tmin = 0.971, Tmax = 0.997	k = −12→12
4086 measured reflections	l = −25→21

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0827P)2] where P = (Fo2 + 2Fc2)/3
1056 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	0.7386 (8)	0.5083 (2)	0.20498 (14)	0.0185 (6)
N2	0.3930 (9)	0.4374 (2)	0.35822 (16)	0.0296 (7)
C1	0.7983 (9)	0.2683 (3)	0.22614 (16)	0.0193 (7)
H1A	0.7552	0.1964	0.2547	0.023*
C2	0.9617 (9)	0.2502 (3)	0.16647 (16)	0.0192 (7)
H2A	1.0368	0.1649	0.1541	0.023*
C3	1.0178 (9)	0.3604 (3)	0.12314 (16)	0.0174 (7)
C4	1.1815 (8)	0.3487 (3)	0.06064 (16)	0.0201 (7)
H4A	1.2662	0.2658	0.0468	0.024*
C5	1.2177 (9)	0.4589 (3)	0.01965 (18)	0.0224 (7)
H5A	1.3204	0.4498	−0.0223	0.027*
C6	1.0989 (8)	0.5855 (3)	0.04129 (17)	0.0239 (8)
H6A	1.1257	0.6595	0.0133	0.029*
C7	0.9466 (9)	0.6018 (3)	0.10188 (17)	0.0213 (7)
H7A	0.8736	0.6866	0.1154	0.026*
C8	0.8981 (8)	0.4894 (3)	0.14492 (17)	0.0162 (7)
C9	0.6962 (8)	0.4002 (3)	0.24322 (16)	0.0169 (7)
C10	0.5263 (9)	0.4229 (3)	0.30714 (17)	0.0196 (7)

	U11	U22	U33	U12	U13	U23
N1	0.0149 (13)	0.0120 (10)	0.0284 (15)	−0.0014 (10)	−0.0013 (13)	−0.0012 (10)
N2	0.0336 (17)	0.0199 (13)	0.0353 (17)	0.0000 (12)	0.0055 (16)	−0.0013 (13)
C1	0.0146 (16)	0.0128 (12)	0.0306 (18)	0.0016 (12)	−0.0030 (15)	0.0009 (12)
C2	0.0155 (16)	0.0113 (12)	0.0307 (18)	0.0009 (12)	−0.0020 (15)	−0.0027 (12)
C3	0.0130 (15)	0.0150 (13)	0.0243 (17)	0.0006 (11)	−0.0063 (14)	−0.0028 (12)
C4	0.0134 (16)	0.0184 (14)	0.0286 (19)	0.0016 (12)	−0.0010 (15)	−0.0060 (13)
C5	0.0164 (16)	0.0251 (15)	0.0256 (17)	−0.0004 (14)	−0.0003 (15)	−0.0006 (13)
C6	0.0218 (17)	0.0167 (13)	0.0333 (19)	−0.0009 (13)	−0.0003 (16)	0.0053 (14)
C7	0.0202 (17)	0.0128 (13)	0.0311 (19)	−0.0003 (13)	−0.0039 (16)	0.0021 (12)
C8	0.0124 (15)	0.0111 (12)	0.0249 (16)	−0.0016 (11)	−0.0027 (14)	−0.0033 (12)
C9	0.0130 (14)	0.0130 (12)	0.0247 (17)	−0.0019 (12)	−0.0035 (14)	−0.0018 (11)
C10	0.0186 (17)	0.0098 (12)	0.0306 (19)	−0.0019 (12)	−0.0015 (15)	0.0008 (12)

N1—C9	1.329 (4)	C4—C5	1.376 (4)
N1—C8	1.360 (4)	C4—H4A	0.9300
N2—C10	1.151 (4)	C5—C6	1.409 (4)
C1—C2	1.359 (4)	C5—H5A	0.9300
C1—C9	1.413 (4)	C6—C7	1.354 (4)
C1—H1A	0.9300	C6—H6A	0.9300
C2—C3	1.414 (4)	C7—C8	1.424 (4)
C2—H2A	0.9300	C7—H7A	0.9300
C3—C4	1.402 (4)	C9—C10	1.452 (4)
C3—C8	1.432 (4)
C9—N1—C8	116.7 (2)	C6—C5—H5A	120.1
C2—C1—C9	117.6 (3)	C7—C6—C5	121.5 (3)
C2—C1—H1A	121.2	C7—C6—H6A	119.3
C9—C1—H1A	121.2	C5—C6—H6A	119.3
C1—C2—C3	120.3 (3)	C6—C7—C8	120.1 (3)
C1—C2—H2A	119.9	C6—C7—H7A	120.0
C3—C2—H2A	119.9	C8—C7—H7A	120.0
C4—C3—C2	123.3 (2)	N1—C8—C7	118.8 (2)
C4—C3—C8	119.3 (3)	N1—C8—C3	122.5 (3)
C2—C3—C8	117.4 (3)	C7—C8—C3	118.7 (3)
C5—C4—C3	120.6 (3)	N1—C9—C1	125.4 (3)
C5—C4—H4A	119.7	N1—C9—C10	115.7 (2)
C3—C4—H4A	119.7	C1—C9—C10	118.8 (3)
C4—C5—C6	119.9 (3)	N2—C10—C9	178.2 (3)
C4—C5—H5A	120.1
C9—C1—C2—C3	−1.4 (4)	C6—C7—C8—N1	−178.8 (3)
C1—C2—C3—C4	−179.4 (3)	C6—C7—C8—C3	0.9 (5)
C1—C2—C3—C8	0.3 (4)	C4—C3—C8—N1	−179.7 (3)
C2—C3—C4—C5	177.7 (3)	C2—C3—C8—N1	0.6 (4)
C8—C3—C4—C5	−2.0 (4)	C4—C3—C8—C7	0.6 (4)
C3—C4—C5—C6	1.9 (5)	C2—C3—C8—C7	−179.1 (3)
C4—C5—C6—C7	−0.4 (5)	C8—N1—C9—C1	−1.0 (5)
C5—C6—C7—C8	−1.0 (5)	C8—N1—C9—C10	179.8 (3)
C9—N1—C8—C7	179.4 (3)	C2—C1—C9—N1	1.8 (5)
C9—N1—C8—C3	−0.3 (4)	C2—C1—C9—C10	−179.0 (3)