Quinoline-2-carbo­nitrile

In the title compound, C₁₀H₆N₂, the mol­ecule 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, mol­ecules are stacked along the a axis by way of weak aromatic π–π stacking inter­actions between the benzene and pyridine rings of adjacent mol­ecules [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_r = 154.17

• Orthorhombic, P 2₁ 2₁ 2₁

• a = 3.8497 (2) Å

• b = 9.9559 (4) Å

• c = 19.9639 (13) Å

• V = 765.16 (7) ų

• 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[F² > 2σ(F²)] = 0.056

• wR(F²) = 0.141

• S = 1.09

• 1056 reflections

• 109 parameters

• H-atom parameters constrained

• Δρ_max = 0.31 e Å⁻³

• Δρ_min = −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).

Supporting information

S1. Comment

Heterocyclic molecules containing cyano group are useful as drug intermediates. Syntheses of the quinoline derivatives were discussed earlier (Sasaki et al., 1998; Reux et al., 2009). Recently, we have synthesized a number of quinoline compounds to investigate the hydrogen bonding patterns in these compounds (Loh et al., 2009; 2010). Herein we report the crystal structure of quinoline-2-carbonitrile.

In the title compound, Fig. 1, the molecule is almost planar with an r.m.s. deviation of 0.014 Å. The dihedral angle between the benzene (C3–C8) and pyridine (C1–C3/N1/C8/C9) rings is 1.28 (16)°. The bond lengths (Allen et al., 1987) and angles in the title compound are within normal ranges and comparable to the related structure of quinoxaline-2-carbonitrile (Fun et al., 2010).

In the crystal packing, Fig. 2, the molecules are stacked along the a axis by way of weak aromatic π–π stacking interactions between the centroid of the benzene (Cg1) and the centroid of the pyridine (Cg2) rings of adjacent molecules [Cg1···Cg2 separation = 3.7943 (19) Å]. There is no significant hydrogen bond observed in this compound.

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).

S2. Experimental

A hot methanol solution (20 ml) of quinoline-2-carbonitrile (39 mg, Aldrich) was warmed over a magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly to room temperature. Colourless plates of (I) appeared after a few days.

S3. Refinement

All H atoms were positioned geometrically with the bond length of C–H being 0.93 Å and were refined using a riding model, with U_iso(H) = 1.2 U_eq(C). In the absence of significant anomalous dispersion, 616 Friedel pairs were merged for the final refinement.

Computing details

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

Figures

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of (I), viewed along the a axis.

Quinoline-2-carbonitrile

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.36 × 0.18 × 0.03 mm

Data collection

Bruker SMART APEXII CCD diffractometer	1056 independent reflections
Radiation source: fine-focus sealed tube	838 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0827P)^2] where P = (Fo^2 + 2Fc^2)/3
1056 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

 

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.