(2-Pyrid-yl)[5-(2-pyridyl-carbon-yl)-2-pyrid-yl]methanone.

In the centrosymmetric title compound, C(17)H(11)N(3)O(2), the dihedral angle between the central and pendant pyridyl rings is 50.29 (9)°. In the crystal, mol-ecules stack along the a axis by π-π inter-actions between the pyridine rings with centroid-centroid distances of 3.845 (2) Å. The N atom and one of the C atoms of the central ring are disordered by symmetry.

Related literature

For studies on other pyridinyl-based methanone species, see: Papaefstathiou & Perlepes (2002 ▶); Dendrinou-Samara et al. (2003 ▶); Crowder et al. (2004 ▶); Chen et al. (2005 ▶); Wan et al. (2008 ▶).

Experimental

Crystal data

C17H11N3O2

M = 289.30

Triclinic,

a = 3.8453 (13) Å

b = 8.447 (3) Å

c = 11.202 (3) Å

α = 108.672 (6)°

β = 97.251 (6)°

γ = 99.772 (6)°

V = 333.29 (19) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.60 × 0.50 × 0.29 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.622, T max = 1.000

2301 measured reflections

1623 independent reflections

1198 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.177

S = 1.07

1623 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033957/jj2048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033957/jj2048Isup2.hkl

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

C17H11N3O2	Z = 1
Mr = 289.30	F(000) = 150
Triclinic, P1	Dx = 1.441 Mg m−3
Hall symbol: -P 1	Melting point: 401 K
a = 3.8453 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.447 (3) Å	Cell parameters from 230 reflections
c = 11.202 (3) Å	θ = 1.9–28.1°
α = 108.672 (6)°	µ = 0.10 mm−1
β = 97.251 (6)°	T = 293 K
γ = 99.772 (6)°	Block, yellow
V = 333.29 (19) Å3	0.60 × 0.50 × 0.29 mm

Bruker APEXII CCD area-detector diffractometer	1623 independent reflections
Radiation source: fine-focus sealed tube	1198 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω–scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Bruker, 2007)	h = −5→4
Tmin = 0.622, Tmax = 1.000	k = −11→11
2301 measured reflections	l = −12→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.096P)2 + 0.0878P] where P = (Fo2 + 2Fc2)/3
1623 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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 > 2σ(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	Occ. (<1)
O1	1.3180 (5)	1.09147 (19)	0.33644 (14)	0.0620 (6)
N1	0.7459 (5)	0.6838 (2)	0.16816 (16)	0.0402 (4)
N2	0.9591 (5)	1.1260 (2)	0.10902 (16)	0.0377 (4)	0.50
C9	0.9591 (5)	1.1260 (2)	0.10902 (16)	0.0377 (4)	0.50
H9A	0.9331	1.2127	0.1798	0.045*	0.50
C1	0.9713 (5)	0.8073 (2)	0.26845 (17)	0.0339 (4)
C2	1.0530 (6)	0.7939 (3)	0.38842 (19)	0.0435 (5)
H2A	1.2108	0.8826	0.4556	0.052*
C3	0.8934 (7)	0.6452 (3)	0.4057 (2)	0.0517 (6)
H3A	0.9378	0.6331	0.4855	0.062*
C4	0.6689 (7)	0.5157 (3)	0.3033 (2)	0.0524 (6)
H4A	0.5633	0.4134	0.3120	0.063*
C5	0.6028 (6)	0.5402 (3)	0.1870 (2)	0.0485 (6)
H5A	0.4502	0.4519	0.1181	0.058*
C6	1.1320 (5)	0.9691 (2)	0.24786 (17)	0.0372 (5)
C7	1.0544 (5)	0.9809 (2)	0.11607 (17)	0.0333 (4)
C8	1.0969 (5)	0.8553 (2)	0.00732 (18)	0.0369 (5)
H8A	1.1642	0.7573	0.0141	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0862 (13)	0.0422 (8)	0.0381 (8)	−0.0157 (8)	−0.0097 (8)	0.0113 (7)
N1	0.0422 (10)	0.0355 (8)	0.0394 (9)	−0.0001 (7)	0.0059 (7)	0.0136 (7)
N2	0.0467 (11)	0.0295 (8)	0.0341 (9)	0.0035 (7)	0.0096 (7)	0.0092 (7)
C9	0.0467 (11)	0.0295 (8)	0.0341 (9)	0.0035 (7)	0.0096 (7)	0.0092 (7)
C1	0.0360 (10)	0.0330 (9)	0.0334 (9)	0.0065 (7)	0.0077 (7)	0.0128 (7)
C2	0.0538 (13)	0.0404 (10)	0.0373 (10)	0.0106 (9)	0.0065 (9)	0.0157 (8)
C3	0.0712 (16)	0.0510 (12)	0.0471 (12)	0.0209 (11)	0.0180 (11)	0.0299 (10)
C4	0.0632 (15)	0.0379 (10)	0.0671 (15)	0.0110 (10)	0.0239 (12)	0.0291 (10)
C5	0.0511 (13)	0.0355 (10)	0.0534 (13)	−0.0015 (9)	0.0097 (10)	0.0140 (9)
C6	0.0421 (11)	0.0328 (9)	0.0326 (9)	0.0012 (8)	0.0041 (8)	0.0108 (7)
C7	0.0333 (10)	0.0298 (8)	0.0335 (9)	−0.0016 (7)	0.0047 (7)	0.0116 (7)
C8	0.0418 (11)	0.0302 (8)	0.0380 (10)	0.0041 (7)	0.0075 (8)	0.0132 (7)

O1—C6	1.216 (2)	C3—C4	1.372 (3)
N1—C5	1.336 (3)	C3—H3A	0.9300
N1—C1	1.341 (2)	C4—C5	1.383 (3)
N2—C8i	1.358 (2)	C4—H4A	0.9300
N2—C7	1.360 (3)	C5—H5A	0.9300
N2—H9A	0.9207	C6—C7	1.507 (2)
C1—C2	1.386 (3)	C7—C8	1.385 (3)
C1—C6	1.501 (3)	C8—C9i	1.358 (2)
C2—C3	1.385 (3)	C8—N2i	1.358 (2)
C2—H2A	0.9300	C8—H8A	0.9300
C5—N1—C1	116.84 (17)	C5—C4—H4A	120.6
C8i—N2—C7	118.59 (16)	N1—C5—C4	123.62 (19)
C8i—N2—H9A	118.5	N1—C5—H5A	118.2
C7—N2—H9A	123.0	C4—C5—H5A	118.2
N1—C1—C2	123.47 (17)	O1—C6—C1	120.89 (17)
N1—C1—C6	117.03 (16)	O1—C6—C7	119.68 (16)
C2—C1—C6	119.48 (17)	C1—C6—C7	119.42 (15)
C3—C2—C1	118.27 (19)	N2—C7—C8	120.92 (17)
C3—C2—H2A	120.9	N2—C7—C6	116.89 (16)
C1—C2—H2A	120.9	C8—C7—C6	122.09 (16)
C4—C3—C2	119.06 (19)	C9i—C8—C7	120.49 (17)
C4—C3—H3A	120.5	N2i—C8—C7	120.49 (17)
C2—C3—H3A	120.5	C9i—C8—H8A	119.8
C3—C4—C5	118.71 (18)	N2i—C8—H8A	119.8
C3—C4—H4A	120.6	C7—C8—H8A	119.8
C5—N1—C1—C2	−1.5 (3)	C2—C1—C6—C7	177.66 (17)
C5—N1—C1—C6	−179.82 (19)	C8i—N2—C7—C8	0.5 (3)
N1—C1—C2—C3	0.0 (3)	C8i—N2—C7—C6	177.03 (17)
C6—C1—C2—C3	178.27 (19)	O1—C6—C7—N2	−45.2 (3)
C1—C2—C3—C4	1.6 (3)	C1—C6—C7—N2	133.4 (2)
C2—C3—C4—C5	−1.6 (4)	O1—C6—C7—C8	131.2 (2)
C1—N1—C5—C4	1.5 (3)	C1—C6—C7—C8	−50.2 (3)
C3—C4—C5—N1	0.0 (4)	N2—C7—C8—C9i	−0.5 (3)
N1—C1—C6—O1	174.7 (2)	C6—C7—C8—C9i	−176.85 (17)
C2—C1—C6—O1	−3.7 (3)	N2—C7—C8—N2i	−0.5 (3)
N1—C1—C6—C7	−4.0 (3)	C6—C7—C8—N2i	−176.85 (17)