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

Archana, R.; Anbazhagan, R.; Sankaran, K.R.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S160053681000070X

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 14.6
Details

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

R. Archana,^a R. Anbazhagan,^b K. R. Sankaran,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^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). For the crystal structures of some aromatic azines, for example, fluorenone azine, see: Hagen et al. (1977). For the other heterocyclic aldehyde azines, see: Chen et al. (1995). For quadratic nonlinear optical properties, see: Wolff & Wortmann (1999).

Experimental

Crystal data

C₂₆H₁₈N₂
M_r = 358.42
Monoclinic, C 2/c
a = 22.8362 (3) Å
b = 13.1432 (2) Å
c = 12.4642 (2) Å
= 92.874 (1)°
V = 3736.31 (10) Å³
Z = 8
Cu K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.955, T_max = 1.000
7177 measured reflections
3682 independent reflections
3147 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.102
S = 1.06
3682 reflections
253 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Hagen, K., Bondybey, V. & Hedberg, K. (1977). J. Am. Chem. Soc. 99, 1365-1371.
Lewis, M. & Glaser, R. (2002). J. Org. Chem. 67, 1441-1447.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wolff, J. J. & Wortmann, R. (1999). Adv. Phys. Org. Chem. 32, 121-217.

organic compounds