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Volume 69 
Part 7 
Page o1033  
July 2013  

Received 17 April 2013
Accepted 24 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.147
Data-to-parameter ratio = 19.5
Details
Open access

4-(Naphthalen-1-yl)pyridine

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: Edwin.Weber@chemie.tu-freiberg.de

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 [pi]-[pi] stacking interactions between the pyridine rings of inversion-related molecules, with a centroid-centroid distance of 3.772 (2) Å. In addition, C-H...[pi] contacts involving an [alpha]-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[Miyaura, N., Yanagy, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.]); Broutin & Colobert (2005[Broutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113-1128.]); Molander & Beaumard (2010[Molander, G. A. & Beaumard, F. (2010). Org. Lett. 12, 4022-4025.]). For [pi]-[pi] stacking interactions, see: James (2004[James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.]). For C-H...[pi] interactions, see: Nishio et al. (2009[Nishio, M., Umezawa, Y., Honda, K., Tsuboyama, S. & Suezawa, H. (2009). CrystEngComm, 11, 1757-1788.]). For non-classic hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.]). For related structures, see: Boeyens et al. (1988[Boeyens, J. C. A., Denner, L. & Perold, G. W. (1988). J. Crystallogr. Spectrosc. Res. 18, 67-73.]); Fabbiani et al. (2006[Fabbiani, F. P. A., Allan, D. R., Parsons, S. & Pulham, C. R. (2006). Acta Cryst. B62, 826-842.]); Suthar et al. (2005[Suthar, B., Fowler, A., Jones, D. S. & Ogle, C. A. (2005). Acta Cryst. E61, o607-o608.]). For aspects of organic crystal engineering, see: Tiekink et al. (2010[Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11N

  • Mr = 205.25

  • Monoclinic, P 21 /n

  • a = 6.8487 (2) Å

  • b = 7.4436 (2) Å

  • c = 21.8378 (5) Å

  • [beta] = 91.833 (1)°

  • V = 1112.70 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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 > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.147

  • S = 1.05

  • 2831 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

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
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT-NT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2007[Bruker (2007). SAINT-NT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2629 ).


References

Boeyens, J. C. A., Denner, L. & Perold, G. W. (1988). J. Crystallogr. Spectrosc. Res. 18, 67-73.  [CrossRef] [ChemPort] [Web of Science]
Broutin, P.-E. & Colobert, F. (2005). Eur. J. Org. Chem. pp. 1113-1128.  [CSD] [CrossRef]
Bruker (2007). SAINT-NT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, ch. 2. Oxford University Press.
Fabbiani, F. P. A., Allan, D. R., Parsons, S. & Pulham, C. R. (2006). Acta Cryst. B62, 826-842.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
James, S. L. (2004). Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 1093-1099. Boca Raton: CRC Press.
Miyaura, N., Yanagy, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.  [CrossRef] [ChemPort] [Web of Science]
Molander, G. A. & Beaumard, F. (2010). Org. Lett. 12, 4022-4025.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Nishio, M., Umezawa, Y., Honda, K., Tsuboyama, S. & Suezawa, H. (2009). CrystEngComm, 11, 1757-1788.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Suthar, B., Fowler, A., Jones, D. S. & Ogle, C. A. (2005). Acta Cryst. E61, o607-o608.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Chichester: Wiley.


Acta Cryst (2013). E69, o1033  [ doi:10.1107/S1600536813014372 ]

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