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Volume 66 
Part 2 
Page o345  
February 2010  

Received 4 January 2010
Accepted 6 January 2010
Online 13 January 2010

Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 14.6
Details
Open access

1-Diphenylmethylene-2-(9H-fluoren-9-ylidene)hydrazine

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India,bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: athiru@vsnl.net

In the title molecule, C26H18N2, the 9H-fluorene unit is almost planar, as the cyclopentadiene ring makes dihedral angles of 1.12 (6) and 1.46 (6)° with the fused benzene rings. The dihedral angle between the two phenyl rings of the diphenylmethylene residue is 61.78 (6)°.

Related literature

For the synthesis, see: Lewis & Glaser (2002[Lewis, M. & Glaser, R. (2002). J. Org. Chem. 67, 1441-1447.]). For the crystal structures of some aromatic azines, for example, fluorenone azine, see: Hagen et al. (1977[Hagen, K., Bondybey, V. & Hedberg, K. (1977). J. Am. Chem. Soc. 99, 1365-1371.]). For the other heterocyclic aldehyde azines, see: Chen et al. (1995[Chen, G. S., Wilbur, J. K., Barnes, C. L. & Glaser, R. (1995). J. Chem. Soc. Perkin. Trans. 2, pp. 2311-2319.]). For quadratic nonlinear optical properties, see: Wolff & Wortmann (1999[Wolff, J. J. & Wortmann, R. (1999). Adv. Phys. Org. Chem. 32, 121-217.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18N2

  • Mr = 358.42

  • Monoclinic, C 2/c

  • a = 22.8362 (3) Å

  • b = 13.1432 (2) Å

  • c = 12.4642 (2) Å

  • [beta] = 92.874 (1)°

  • V = 3736.31 (10) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.58 mm-1

  • T = 110 K

  • 0.46 × 0.41 × 0.32 mm

Data collection
  • Oxford Xcalibur diffractometer with a Ruby Gemini detector

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.955, Tmax = 1.000

  • 7177 measured reflections

  • 3682 independent reflections

  • 3147 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.06

  • 3682 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2612 ).


Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Chen, G. S., Wilbur, J. K., Barnes, C. L. & Glaser, R. (1995). J. Chem. Soc. Perkin. Trans. 2, pp. 2311-2319.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hagen, K., Bondybey, V. & Hedberg, K. (1977). J. Am. Chem. Soc. 99, 1365-1371.  [CrossRef] [ChemPort] [ISI]
Lewis, M. & Glaser, R. (2002). J. Org. Chem. 67, 1441-1447.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wolff, J. J. & Wortmann, R. (1999). Adv. Phys. Org. Chem. 32, 121-217.  [CrossRef] [ChemPort]


Acta Cryst (2010). E66, o345  [ doi:10.1107/S160053681000070X ]

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