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Volume 68 
Part 1 
Page o81  
January 2012  

Received 24 November 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 170 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.144
Data-to-parameter ratio = 17.2
Details
Open access

1,2-Bis(3-phenoxybenzylidene)hydrazine

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
Correspondence e-mail: jjasinski@keene.edu

Molecules of the title compound, C26H20N2O2, reside on crystallographic centres of inversion located at the mid-point of the N-N bond. The benzylidene ring is essentially coplanar with the central hydrazine group, with an interplanar angle of 4.5 (2)°, whereas the phenyl ring is oriented at 34.0 (3)° with respect to the mean plane of the central 1,2-dibenzylidenehydrazine group. In the crystal, C-H...[pi](arene)-ring interactions link molecules about inversion centres.

Related literature

For the biological activity of Schiff bases, see: Aydogan et al. (2001[Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]); Desai et al. (2001[Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.]); El-masry et al. (2000[El-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.]); Hodnett & Dunn (1970[Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768-770.]); Kundu et al. (2005[Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.]); Singh & Dash (1988[Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.]); Taggi et al. (2002[Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.]); Xu et al. (1997[Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.]); For crystallography and coordination chemistry of compounds containing the azine functionality or a diimine linkage, see: Xu et al. (1997[Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.]); Kundu et al. (2005[Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.]); For related structures, see: Liu et al. (2007[Liu, G., Xie, L., Wang, Y. & Wang, J.-D. (2007). Acta Cryst. E63, o2611.]); Odabasoglu et al. (2007[Odabasoglu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145-o4146.]); Zhang & Zheng (2008[Zhang, C.-N. & Zheng, Y.-F. (2008). Acta Cryst. E64, o36.]); Zheng et al. (2005a[Zheng, P.-W., Wang, W. & Duan, X.-M. (2005a). Acta Cryst. E61, o3485-o3486.],b[Zheng, P.-W., Wang, W. & Duan, X.-M. (2005b). Acta Cryst. E61, o3020-o3021.]). For standard bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H20N2O2

  • Mr = 392.44

  • Monoclinic, C 2/c

  • a = 23.6271 (16) Å

  • b = 11.2942 (6) Å

  • c = 8.2359 (7) Å

  • [beta] = 109.538 (8)°

  • V = 2071.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 170 K

  • 0.44 × 0.20 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.966, Tmax = 0.995

  • 4228 measured reflections

  • 2341 independent reflections

  • 1643 reflections with I > 2[sigma](I)

  • Rint = 0.023

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

  • wR(F2) = 0.144

  • S = 1.05

  • 2341 reflections

  • 136 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7-C12 benzylidene ring.

D-H...A D-H H...A D...A D-H...A
C5-H5A...Cgi 0.93 2.68 3.5947 (17) 167
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2067 ).


Acknowledgements

ASP thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.
Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.  [ChemPort]
Desai, S. B., Desai, P. B. & Desai, K. R. (2001). Heterocycl. Commun. 7, 83-90.  [ChemPort]
El-masry, A. H., Fahmy, H. H. & Abdelwahed, S. H. A. (2000). Molecules, 5, 1429-1438.  [ChemPort]
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768-770.  [CrossRef] [ChemPort] [PubMed] [ISI]
Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.  [CSD] [CrossRef] [details]
Liu, G., Xie, L., Wang, Y. & Wang, J.-D. (2007). Acta Cryst. E63, o2611.  [CSD] [CrossRef] [details]
Odabasoglu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145-o4146.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.  [ISI] [CrossRef] [PubMed] [ChemPort]
Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.  [CrossRef] [ChemPort] [ISI]
Zhang, C.-N. & Zheng, Y.-F. (2008). Acta Cryst. E64, o36.  [CSD] [CrossRef] [details]
Zheng, P.-W., Wang, W. & Duan, X.-M. (2005a). Acta Cryst. E61, o3485-o3486.  [CSD] [CrossRef] [details]
Zheng, P.-W., Wang, W. & Duan, X.-M. (2005b). Acta Cryst. E61, o3020-o3021.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o81  [ doi:10.1107/S1600536811052469 ]

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