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Volume 69 
Part 2 
Page o307  
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) = 0.002 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 21.7
Details
Open access

1-[3-(Naphthalen-1-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 1-naphthalene substituents, which are essentially planar (r.m.s. deviation = 0.039 and 0.027 Å). The conformation is mixed syn/anti, with equivalent torsion angles about the benzene-naphthalene bonds of 121.46 (11) and 51.58 (14)°.

Related literature

For synthesis of the title compound, see: 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.]); Wolfenden et al. (2013[Wolfenden, M. L., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o308.]). For MM2 calculations, see: CambridgeSoft (2010[CambridgeSoft (2010). Chem3DPro. CambridgeSoft Corporation, Cambridge, MA, USA.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18

  • Mr = 330.4

  • Triclinic, [P \overline 1]

  • a = 7.6272 (1) Å

  • b = 10.8453 (2) Å

  • c = 11.8454 (2) Å

  • [alpha] = 106.0798 (8)°

  • [beta] = 96.2976 (8)°

  • [gamma] = 108.4307 (9)°

  • V = 872.05 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.28 × 0.22 × 0.15 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 = 0.980, Tmax = 0.989

  • 11174 measured reflections

  • 6272 independent reflections

  • 4659 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.138

  • S = 1.05

  • 6272 reflections

  • 289 parameters

  • Only H-atom coordinates refined

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.25 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: TK5189 ).


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]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
CambridgeSoft (2010). Chem3DPro. CambridgeSoft Corporation, Cambridge, MA, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lin, Y. C. & Williams, D. E. (1975). Acta Cryst. B31, 318-320.  [CrossRef] [details]
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]
Wolfenden, M. L., Dhar, R. K., Fronczek, F. R. & Watkins, S. F. (2013). Acta Cryst. E69, o308.  [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, o307  [ doi:10.1107/S1600536813002407 ]

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