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Volume 69 
Part 12 
Page o1755  
December 2013  

Received 29 October 2013
Accepted 4 November 2013
Online 9 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 17.2
Details
Open access

5,5'-Bis(benz­yloxy)-2,2'-[hydrazine­diylidenebis(methanylyl­idene)]diphenol

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
Correspondence e-mail: eesans@yahoo.com

The title azine mol­ecule, C28H24N2O4, lies about a center of inversion. The dihedral angle between the phenyl ring and the hy­droxy-substituted ring is 70.3 (5)°. The phenolic O-H group forms an intra­molecular hydrogen bond to the azine N atom.

Related literature

For the biological activity of azines, see: Gul et al. (2003[Gul, H. I., Gul, M., Vepsalainen, J., Erciyas, E. & Hanninen, O. (2003). Biol. Pharm. Bull. 26, 631-637.]); Kumaraswamy & Vaidya (2005[Kumaraswamy, M. N. & Vaidya, V. P. (2005). Indian J. Heterocycl. Chem. 14, 193-196.]). For related structures, see: Acrovito et al. (1969[Acrovito, G., Bonamico, M., Dornenicano, A. & Vaciago, A. (1969). J. Chem. Soc. B, pp. 173-742.]); Sithambaresan & Kurup (2011[Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.]). For a related synthesis, see: Karmakar et al. (2007[Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). Polyhedron, 26, 1347-1355.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24N2O4

  • Mr = 452.49

  • Monoclinic, P 21 /n

  • a = 12.4748 (17) Å

  • b = 5.3630 (6) Å

  • c = 17.021 (2) Å

  • [beta] = 90.699 (5)°

  • V = 1138.7 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.982

  • 6320 measured reflections

  • 2738 independent reflections

  • 1593 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.122

  • S = 1.01

  • 2738 reflections

  • 159 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2'...N1 0.87 (2) 1.84 (2) 2.625 (2) 148 (2)

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5346 ).


Acknowledgements

NRS thanks the Council of Scientific and Industrial Research (India) for a Junior Research Fellowship. MRPK thanks the University Grants Commission, New Delhi, for a UGC-BSR one-time grant to faculty. The authors thank the Sophisticated Analytical Instruments Facility, Cochin University of S & T, for the diffraction measurements.

References

Acrovito, G., Bonamico, M., Dornenicano, A. & Vaciago, A. (1969). J. Chem. Soc. B, pp. 173-742.
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gul, H. I., Gul, M., Vepsalainen, J., Erciyas, E. & Hanninen, O. (2003). Biol. Pharm. Bull. 26, 631-637.  [CrossRef] [PubMed] [ChemPort]
Karmakar, A., Sarma, R. J. & Baruah, J. B. (2007). Polyhedron, 26, 1347-1355.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Kumaraswamy, M. N. & Vaidya, V. P. (2005). Indian J. Heterocycl. Chem. 14, 193-196.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.  [CSD] [CrossRef] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1755  [ doi:10.1107/S1600536813030171 ]

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