4-(Naphthalen-1-yl)pyridine

Antje Vetter; Wilhelm Seichter; Edwin Weber

doi:10.1107/S1600536813014372

. 2013 Jun 8;69(Pt 7):o1033. doi: 10.1107/S1600536813014372

4-(Naphthalen-1-yl)pyridine

Antje Vetter ^a, Wilhelm Seichter ^a, Edwin Weber ^a,^*

PMCID: PMC3952235 PMID: 24627683

Abstract

In the title compound, C₁₅H₁₁N, the mean planes of the aromatic moieties are inclined to one another by 72.9 (1)°. The crystal is stabilized by π–π stacking interactions between the pyridine rings of inversion-related molecules, with a centroid–centroid distance of 3.772 (2) Å. In addition, C—H⋯π contacts involving an α-C—H group of the pyridine ring and the nonsubstituted ring of the naphthalene unit are observed, giving rise to a herringbone-type supramolecular architecture of the naphthalene moiety being contained in the molecule.

Related literature

For preparative methods and the characterization of the title compound, see: Miyaura et al. (1981 ▶); Broutin & Colobert (2005 ▶); Molander & Beaumard (2010 ▶). For π–π stacking interactions, see: James (2004 ▶). For C—H⋯π interactions, see: Nishio et al. (2009 ▶). For non-classic hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For related structures, see: Boeyens et al. (1988 ▶); Fabbiani et al. (2006 ▶); Suthar et al. (2005 ▶). For aspects of organic crystal engineering, see: Tiekink et al. (2010 ▶). graphic file with name e-69-o1033-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₁N
M _r = 205.25
Monoclinic,
a = 6.8487 (2) Å
b = 7.4436 (2) Å
c = 21.8378 (5) Å
β = 91.833 (1)°
V = 1112.70 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 193 K
0.53 × 0.43 × 0.43 mm

Data collection

Bruker X8 APEX CCD diffractometer
14800 measured reflections
2831 independent reflections
2302 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.147
S = 1.05
2831 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-NT (Bruker, 2007 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014372/fj2629sup1.cif

e-69-o1033-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014372/fj2629Isup2.hkl

e-69-o1033-Isup2.hkl^{(139KB, hkl)}

Click here for additional data file.^{(4.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813014372/fj2629Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1ⁱ	0.93	2.69	3.577 (2)	161
C14—H14⋯Cg1ⁱⁱ	0.93	2.84	3.648 (2)	146

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Molecules having a defined structure with rather predictable supramolecular interactions of their construction elements and functional groups such as π···π (James, 2004) or weak hydrogen bonding contacts (Desiraju & Steiner,1999) are helpful in gaining deeper insight into the principles of crystal engineering (Tiekink et al., 2010). This has stimulated to determine the crystal structure of the title compound being composed of two π-systems of different electronic nature (naphthalene and pyridine units) and having potential capability of weak C—H···π (Nishio et al., 2009) or C—H···N bonding (Desiraju & Steiner, 1999). In the crystal structure, the bond distances both of the naphthalene (AB) and pyridine (C) parts agree well with those found for related compounds (Boeyens et al., (1988) Suthar et al., 2005). The naphthalene moiety shows a slight distortion from strict planarity with largest atomic distances from the best plane being 0.029 (1) Å for C7 and -0.030 (2) Å for C9. The mean planes of the naphthalene and pyridine moieties are inclined to one another by 72.9 (1) ° (Fig. 1). Contrary to expectations, the nitrogen of the heterocyclic ring is excluded from molecular association. Instead, the crystal structure is stabilized by weaker C—H···π contacts with the non-substituted ring of the naphthalene unit (B) acting as an acceptor [C6—H6···centroid(B) 2.69 Å, 161 °, C14—H14···centroid(B) 2.84 Å, 146 °]. Moreover, the centre···centre distance of 3.772 (2) Å between the pyridine rings of inversion related molecules indicate the occurrence of π···π stacking interactions (Fig. 2). In a similar fashion as in the crystal structure of naphthalene (Fabbiani et al., 2006), each molecule is surrounded by another six molecules so that their naphthalene elements form a herringbone motif.

Experimental

Preparation of the title compound was achieved by a Suzuki cross coupling reaction (Miyaura et al., 1981) between 2-(1-naphthyl)-1,3,2-dioxaborolane (Broutin & Colobert, 2005) (4.94 g, 25 mmol) and 4-bromopyridinium hydrochloride (4.87 g, 25 mmol) in the presence of tetrakis(triphenylphosphane)palladium (0.52 g, 0.45 mmol) and potassium phosphate (7.24 g, 34 mmol) in 136 ml degassed N,N-dimethylformamide. The resulting mixture was heated to 100 °C and stirred at this temperature for 6 h. After cooling to room temperature, the mixture was extracted with toluene. The extract was washed with saturated aqueous NaCl solution and dried (Na₂SO₄). Evaporation of the solvent and crystallization from ethanol yielded 1.10 g (24%) colourless crystals. M.p. (366–368 K). Spectroscopic data correspond to those reported for the compound obtained via a different synthetic route (Molander & Beaumard, 2010).