1-[6-(6-Acetyl­pyridin-2-yl)pyridin-2-yl]ethanone

Huseyin Zekeriya Dogan; Abdurrahman Sengul; Simon John Coles

doi:10.1107/S160053681101556X

. 2011 May 7;67(Pt 6):o1295. doi: 10.1107/S160053681101556X

1-[6-(6-Acetylpyridin-2-yl)pyridin-2-yl]ethanone

Huseyin Zekeriya Dogan ^a, Abdurrahman Sengul ^a,^*, Simon John Coles ^b

PMCID: PMC3120622 PMID: 21754701

Abstract

In the title compound, C₁₄H₁₂N₂O₂, the asymmetric unit comprises one half-molecule 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, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, forming a supramolecular 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 _r = 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
Δρ_max = 0.26 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-67-o1295-sup1.cif^{(11.2KB, cif)}

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

e-67-o1295-Isup2.hkl^{(64.6KB, hkl)}

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

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

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the research project fund of Zonguldak Karaelmas University (grant No. 2010–13–02–04) and the UK Engineering and Physical Sciences Research Council.

supplementary crystallographic information

Comment

The principles of supramolecular chemistry provide guidelines for the construction of quite complex molecules or constructs from relatively simple components. In this respect, 6,6'-diacetyl-2,2'-bipyridine, acting as a diketone has been widely used as a precursor or building block for the construction of polypyridine bridging ligands [Şengül et al., 2009; Agac et al., 2010; Potts et al., 1993; Zong et al., 2006]. The well established coordination ability of 2,2'-bipyridine suggests that ligands containing multiple pyridine rings joined through their 2,6-positions would be ideal for the self-assembly of mono-, double-, or triple-stranded helicates containing one or more transition-metal cations and producing a variety of coordination geometries and architectures. This area is therefore of interest with respect to supramolecular chemistry as a precursor for polypyridyl bridging ligands (Janiak et al., 1999; Potts et al., 1993; Zong et al., 2006) and derivatives are important materials for the preparation of oximes or other funcionalities (Iyoda et al., 1990; Parks et al., 1973; Agac et al., 2010).

As a continuation of work on the structures of such compounds (Şengül et al., 1998) the title compound derived from the coupling of 6-bromo-2-acetylpyridine is reported herein. The molecule of the title compound (Fig. 1.) possesses a twofold symmetry where each of the pyridyl rings are trans to each other, forming an essentially planar structure. The bond lengths have normal values (Şengül et al., 1998), and are comparable to those observed in similar compounds (Janiak et al., 1999; O'Donnell & Steel, 2010; Kochel, 2005; Şengül et al. 2009).

In the crystal, molecules are linked through intermolecular C-H···O H-bonds (Table 1) to form a supramolecular network parallel to (100) (Fig. 1).

Experimental

The title compound was synthesized by the reported method of homocoupling of aryl halides using Ni(II) complex and zinc in the presence of triphenylphosphine by Janiak et al. (1999). The spectroscopic and analytical data are in good agreement with the reported values in literature by Zong et al., 2006; Potts et al., 1993; Agac et al., 2010 and Parks et al., 1973. The solid was crystallized from dichloromethane to afford colourless needless suitable for X-ray diffraction. Mp.: 178.5–179.5 °C. ¹H-NMR (dmso-d₆, δ_p.p.m.): 8.81(d, 2H, J_3,4 = 8 Hz, H3,3'), 8.23(d, 2H, J_5,4 = 7 Hz, H5,5'), 8.07(dd, 2H, J_4,3 = 8.2 Hz, J_4,5 = 1 Hz, H4,4'), 2.79(s, 6H, 2xCH₃). Calc. for C₁₄H₁₂N₂O₂: C, 69,99; H, 5,03; N, 11,66 Found: C,62,54; H, 4,54; N, 11,68%. IR (ATR, ν cm^-1): 3056 (CH_ar), 2990 (CH_al), 1590 (C=O), 1487 and 1437 (C=N and C=C), 1311, 1182, 1120, 1094, 1071, 995, 861, 748, 720. UV-Vis (MeCN, λ_max/nm): 286, 258, 219.