1-[6-(6-Acetyl-pyridin-2-yl)pyridin-2-yl]ethanone.

In the title compound, C(14)H(12)N(2)O(2), the asymmetric unit comprises one half-mol-ecule with an inversion center between the pyridine rings. The rings are trans coplanar with the acetyl groups deviating slightly from the mean planes, making a dihedral angle of 4.63 (4)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds, forming a supra-molecular sheet parallel to (100).

Related literature

The compound is of inter­est with respect to supra­molecular chemistry as a precursor for polypyridyl bridging ligands. For related structures, see: Parks et al. (1973 ▶); Potts et al. (1993 ▶); Zong et al. (2006 ▶); Şengül et al. (1998) ▶; Agac et al. (2010 ▶); Iyoda et al. (1990 ▶); Janiak et al. (1999 ▶); O’Donnell & Steel (2010 ▶); Kochel (2005 ▶). For applications of related structures, see: Parks et al. (1973 ▶); Iyoda et al. (1990 ▶); Şengül et al. (2009 ▶); Agac et al. (2010 ▶).

Experimental

Crystal data

C14H12N2O2

M = 240.26

Monoclinic,

a = 3.9338 (2) Å

b = 13.8005 (8) Å

c = 10.8728 (6) Å

β = 94.437 (4)°

V = 588.50 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.50 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer with APEXII area detector

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.955, T max = 0.982

10564 measured reflections

1336 independent reflections

1220 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.105

S = 1.10

1336 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101556X/bq2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101556X/bq2286Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101556X/bq2286Isup3.cml

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

C14H12N2O2	F(000) = 252
Mr = 240.26	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Melting point: 452 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 3.9338 (2) Å	Cell parameters from 10564 reflections
b = 13.8005 (8) Å	θ = 2.9–27.5°
c = 10.8728 (6) Å	µ = 0.09 mm−1
β = 94.437 (4)°	T = 120 K
V = 588.50 (6) Å3	Rod, colourless
Z = 2	0.50 × 0.20 × 0.20 mm

Bruker–Nonius Kappa CCD diffractometer with APEXII area detector	1336 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1220 reflections with I > 2σ(I)
10cm confocal mirrors	Rint = 0.034
φ and ω scans	θmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −5→4
Tmin = 0.955, Tmax = 0.982	k = −17→17
10564 measured reflections	l = −14→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3
1336 reflections	(Δ/σ)max = 0.001
83 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.4161 (3)	0.54168 (8)	0.46613 (10)	0.0185 (3)
C2	0.4431 (3)	0.63598 (9)	0.51269 (11)	0.0234 (3)
H2	0.5670	0.6485	0.5895	0.028*
C3	0.2863 (3)	0.71096 (9)	0.44508 (12)	0.0277 (3)
H3	0.3018	0.7757	0.4748	0.033*
C4	0.1063 (3)	0.69010 (9)	0.33338 (12)	0.0248 (3)
H4	−0.0011	0.7402	0.2846	0.030*
C5	0.0871 (3)	0.59397 (8)	0.29474 (10)	0.0197 (3)
C6	−0.1175 (3)	0.56675 (9)	0.17703 (11)	0.0216 (3)
C7	−0.1483 (3)	0.46102 (9)	0.14615 (11)	0.0247 (3)
H7A	−0.2969	0.4528	0.0703	0.037*
H7B	−0.2460	0.4266	0.2139	0.037*
H7C	0.0780	0.4346	0.1341	0.037*
N1	0.2396 (2)	0.52066 (7)	0.35884 (9)	0.0190 (2)
O1	−0.2556 (3)	0.62953 (7)	0.11205 (8)	0.0315 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0184 (5)	0.0192 (6)	0.0174 (5)	−0.0012 (4)	−0.0011 (4)	0.0013 (4)
C2	0.0270 (6)	0.0206 (6)	0.0215 (6)	−0.0012 (5)	−0.0047 (5)	−0.0012 (4)
C3	0.0333 (7)	0.0185 (6)	0.0297 (7)	0.0004 (5)	−0.0073 (5)	−0.0017 (5)
C4	0.0275 (6)	0.0199 (6)	0.0259 (6)	0.0018 (5)	−0.0053 (5)	0.0032 (5)
C5	0.0199 (6)	0.0200 (6)	0.0189 (5)	0.0005 (4)	−0.0012 (4)	0.0018 (4)
C6	0.0210 (6)	0.0234 (6)	0.0199 (6)	0.0019 (4)	−0.0019 (4)	0.0016 (4)
C7	0.0258 (6)	0.0245 (6)	0.0225 (6)	0.0006 (5)	−0.0063 (5)	−0.0017 (5)
N1	0.0191 (5)	0.0197 (5)	0.0178 (5)	0.0000 (4)	−0.0014 (4)	0.0016 (4)
O1	0.0384 (6)	0.0282 (5)	0.0259 (5)	0.0068 (4)	−0.0104 (4)	0.0033 (4)

C1—N1	1.3423 (15)	C4—H4	0.9500
C1—C2	1.3975 (16)	C5—N1	1.3433 (14)
C1—C1i	1.492 (2)	C5—C6	1.5058 (16)
C2—C3	1.3861 (17)	C6—O1	1.2189 (15)
C2—H2	0.9500	C6—C7	1.5000 (17)
C3—C4	1.3878 (17)	C7—H7A	0.9800
C3—H3	0.9500	C7—H7B	0.9800
C4—C5	1.3919 (17)	C7—H7C	0.9800
N1—C1—C2	122.39 (11)	N1—C5—C6	116.16 (10)
N1—C1—C1i	116.22 (12)	C4—C5—C6	120.48 (10)
C2—C1—C1i	121.39 (13)	O1—C6—C7	122.48 (11)
C3—C2—C1	119.01 (11)	O1—C6—C5	120.02 (11)
C3—C2—H2	120.5	C7—C6—C5	117.49 (10)
C1—C2—H2	120.5	C6—C7—H7A	109.5
C2—C3—C4	119.03 (11)	C6—C7—H7B	109.5
C2—C3—H3	120.5	H7A—C7—H7B	109.5
C4—C3—H3	120.5	C6—C7—H7C	109.5
C3—C4—C5	118.28 (11)	H7A—C7—H7C	109.5
C3—C4—H4	120.9	H7B—C7—H7C	109.5
C5—C4—H4	120.9	C1—N1—C5	117.92 (10)
N1—C5—C4	123.35 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ii	0.95	2.56	3.2992 (16)	135.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.56	3.2992 (16)	135

Symmetry code: (i) .