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Volume 69 
Part 2 
Page o308  
February 2013  

Received 17 January 2013
Accepted 23 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.045
wR = 0.125
Data-to-parameter ratio = 21.6
Details
Open access

2-[3-(Naphthalen-2-yl)phenyl]naphthalene1

aDepartment of Chemistry, Louisiana State University, Baton Rouge LA, 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C26H18, consists of a benzene ring with meta-substituted 2-naphthalene substituents, which are essentially planar [r.m.s. deviations = 0.022 (1) and 0.003 (1) Å]. The conformation is syn, with equivalent torsion angles about the benzene-naphthalene bonds of -36.04 (13) and +34.14 (13)°. The molecule has quasi-Cs molecular symmetry.

Related literature

For properties of oligophenyls, see: Bocchinfuso et al. (2009[Bocchinfuso, G., Mazzuca, C., Palleschi, A., Pizzoferrato, R. & Tagliatesta, P. (2009). J. Phys. Chem. A, 113, 14887-14895.]) and for their synthesis, see: Marcinow & Rabideau (1990[Marcinow, Z. & Rabideau, P. (1990). J. Org. Chem. 55, 3812-3816.]); Du et al. (1986[Du, C. J. F., Hart, H. & Ng, K. K. D. (1986). J. Org. Chem. 51, 3162-3165.]); Woods et al. (1951[Woods, G. F., Reed, F. T., Arthur, T. E. & Ezekiel, H. (1951). J. Am. Chem. Soc. 73, 3854-3856.]). For similar structures, see: Baker et al. (1990[Baker, K. N., Fratini, A. V. & Adams, W. W. (1990). Polymer, 31, 1623-1631.]); Lin & Williams (1975[Lin, Y. C. & Williams, D. E. (1975). Acta Cryst. B31, 318-320.]); Bart (1968[Bart, J. C. J. (1968). Acta Cryst. B24, 1277-1287.]); Tummala et al. (2013[Tummala, M., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o307.]). For conformational calculations with GAUSSIAN09, see: Frisch et al. (2009[Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian, Inc., Wallingford, CT, USA.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18

  • Mr = 330.4

  • Orthorhombic, P b c n

  • a = 25.9304 (3) Å

  • b = 8.9300 (1) Å

  • c = 14.9377 (2) Å

  • V = 3458.95 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.40 × 0.27 × 0.22 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.972, Tmax = 0.984

  • 37425 measured reflections

  • 6240 independent reflections

  • 4993 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.125

  • S = 1.02

  • 6240 reflections

  • 289 parameters

  • Only H-atom coordinates refined

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: COLLECT (Nonius 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2619 ).


Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ESH-TR-13, administered by the Louisiana Board of Regents.

References

Baker, K. N., Fratini, A. V. & Adams, W. W. (1990). Polymer, 31, 1623-1631.  [CrossRef] [ChemPort]
Bart, J. C. J. (1968). Acta Cryst. B24, 1277-1287.  [CrossRef] [ChemPort] [details] [ISI]
Bocchinfuso, G., Mazzuca, C., Palleschi, A., Pizzoferrato, R. & Tagliatesta, P. (2009). J. Phys. Chem. A, 113, 14887-14895.  [CrossRef] [ChemPort] [PubMed]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Du, C. J. F., Hart, H. & Ng, K. K. D. (1986). J. Org. Chem. 51, 3162-3165.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian, Inc., Wallingford, CT, USA.
Lin, Y. C. & Williams, D. E. (1975). Acta Cryst. B31, 318-320.  [CrossRef] [details]
Marcinow, Z. & Rabideau, P. (1990). J. Org. Chem. 55, 3812-3816.  [CrossRef] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tummala, M., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o307.  [CrossRef] [details]
Woods, G. F., Reed, F. T., Arthur, T. E. & Ezekiel, H. (1951). J. Am. Chem. Soc. 73, 3854-3856.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o308  [ doi:10.1107/S1600536813002390 ]

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