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Volume 69 
Part 4 
Pages o581-o582  
April 2013  

Received 4 March 2013
Accepted 17 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.072
wR = 0.218
Data-to-parameter ratio = 13.0
Details
Open access

1-{[4-(4-{[(2-Oxidonaphthalen-1-yl)methylidene]azaniumyl}phenoxy)phenyl]iminiumylmethyl}naphthalen-2-olate

aLaboratoire d'Électrochimie des Matériaux Moléculaires et Complexes (LEMMC), Département de Génie des Procèdes, Faculté de Technologie, Université FERHAT ABBAS - SETIF, 19000, Algeria
Correspondence e-mail: daoudkamal88@yahoo.fr

The title Schiff base compound, C34H24N2O3, was prepared by a condensation reaction of bifunctional aromatic diamine (4,4'-diaminodiphenyl ether) with hydroxynaphtaldehyde. The asymmetric unit contains two independent molecules with similar conformations. The compound contains a central oxygen bridge and two functionalized [(E)-(phenyliminio)methyl]naphthalen-2-olate units. The dihedral angles between the benzene rings linking to the central O atom are 74.64 (19) and 69.85 (18)° in the two independent molecules. Intramolecular O-H...O hydrogen bonding occurs between the protonated imino N atoms and deprotonated hydroxy O atoms in both molecules. In the crystal, weak C-H...O hydrogen bonds are observed.

Related literature

For biological and pharmacological activities of Schiff base compounds and their derivatives, see: Khandar et al. (2005[Khandar, A. A., Hosseini-Yazdi, S. A. & Zarei, S. A. (2005). Inorg. Chim. Acta, 358, 3211-3217.]); Chen et al. (2006[Chen, Y., Zhao, Y., Lu, C., Tzeng, C. & Wang, J. (2006). Bioorg. Med. Chem. 14, 4373-4378.]); Kidwai et al. (2000[Kidwai, M., Bhushan, K., Sapra, P., Saxena, R. & Gupta, R. (2000). Bioorg. Med. Chem. 8, 69-72.]); de Souza et al. (2005[Souza, M. V. N. (2005). Mini Rev. Med. Chem. 5, 1009-1017.]). For their application in water treatments, see: Izatt et al. (1995[Izatt, R. M., Pawlak, M. K. & Bardshaw, I. S. (1995). Chem. Rev. 95, 2529-2586.]); Kalcher et al. (1995[Kalcher, K., Kauffman, J. M., Wank, J., Vaneare, I. S., Vitras, K., Neuhal, C. & Yang, Z. (1995). Electroanalysis, 7, 5-22.]); Gilmartin & Hart (1995[Gilmartin, M. A. T. & Hart, J. P. (1995). Analyst, 120, 1029-1045.]) and as corrosion inhibitors, see: Ahamad et al. (2010[Ahamad, I., Prasad, R. & Quraishi, M. A. (2010). Corros. Sci. 52, 933-942.]); Negm et al. (2010[Negm, N. A., Elkholy, Y. M., Zahran, M. K. & Tawfik, S. M. (2010). Corros. Sci. 52, 3523-3536.]); Zhenlan et al., (2002[Zhenlan, Q., Shenhao, C., Ying, L. & Xuegui, C. (2002). Corros. Sci. 44, 703-715.]). For crystallographic studies of related compounds, see: Girija et al. (2004[Girija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S. (2004). Acta Cryst. E60, o586-o588.]); Djamel et al. (2011[Djamel, D., Tahar, D., Djahida, H., Hanane, H. & Salah, C. (2011). Acta Cryst. E67, o1119-o1120.]); Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o3087.]). For the synthesis, see: Issaadi et al. (2005[Issaadi, S., Haffar, D., Douadi, T., Chafaa, S., Séraphin, D., Khan, M. A. & Boue, G. M. (2005). Synth. React. Inorg. Met-Org. Nano-Met. Chem. 35, 875-882.]); Ghames et al. (2006[Ghames, A., Douadi, T., Haffar, D., Chafaa, S., Allain, M., Khan, M. A. & Bouet, G. M. (2006). Polyhedron, 25, 3201-3208.]).

[Scheme 1]

Experimental

Crystal data
  • C34H24N2O3

  • Mr = 508.55

  • Triclinic, [P \overline 1]

  • a = 5.292 (1) Å

  • b = 20.203 (1) Å

  • c = 23.863 (1) Å

  • [alpha] = 87.853 (10)°

  • [beta] = 86.457 (10)°

  • [gamma] = 85.26 (1)°

  • V = 2536.4 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.5 × 0.1 × 0.1 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 15547 measured reflections

  • 9159 independent reflections

  • 4705 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.218

  • S = 1.02

  • 9159 reflections

  • 706 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2 0.86 1.83 2.533 (4) 138
N2-H2...O3 0.86 1.82 2.530 (4) 138
N3-H3...O5 0.86 1.84 2.543 (4) 138
N4-H4A...O6 0.86 1.82 2.522 (4) 138
C20-H20...O2i 0.93 2.46 3.236 (5) 141
C46-H46...O3 0.93 2.37 3.085 (5) 134
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: COLLECT (Nonius, 1999)[Nonius (1999). 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: SHELXS86 (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.]); 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: XU5684 ).


Acknowledgements

The authors thank Dr Lahcene Ouahab for the data collection at the Centre de Diffractométrie de l'Université de Rennes 1 CDiFX.

References

Ahamad, I., Prasad, R. & Quraishi, M. A. (2010). Corros. Sci. 52, 933-942.  [CrossRef] [ChemPort]
Chen, Y., Zhao, Y., Lu, C., Tzeng, C. & Wang, J. (2006). Bioorg. Med. Chem. 14, 4373-4378.  [CrossRef] [PubMed] [ChemPort]
Djamel, D., Tahar, D., Djahida, H., Hanane, H. & Salah, C. (2011). Acta Cryst. E67, o1119-o1120.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ghames, A., Douadi, T., Haffar, D., Chafaa, S., Allain, M., Khan, M. A. & Bouet, G. M. (2006). Polyhedron, 25, 3201-3208.  [ISI] [CSD] [CrossRef] [ChemPort]
Gilmartin, M. A. T. & Hart, J. P. (1995). Analyst, 120, 1029-1045.  [CrossRef] [ChemPort] [PubMed]
Girija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S. (2004). Acta Cryst. E60, o586-o588.  [CrossRef] [details]
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o3087.  [CSD] [CrossRef] [details]
Issaadi, S., Haffar, D., Douadi, T., Chafaa, S., Séraphin, D., Khan, M. A. & Boue, G. M. (2005). Synth. React. Inorg. Met-Org. Nano-Met. Chem. 35, 875-882.  [CrossRef] [ChemPort]
Izatt, R. M., Pawlak, M. K. & Bardshaw, I. S. (1995). Chem. Rev. 95, 2529-2586.  [CrossRef] [ChemPort] [ISI]
Kalcher, K., Kauffman, J. M., Wank, J., Vaneare, I. S., Vitras, K., Neuhal, C. & Yang, Z. (1995). Electroanalysis, 7, 5-22.  [CrossRef] [ChemPort]
Khandar, A. A., Hosseini-Yazdi, S. A. & Zarei, S. A. (2005). Inorg. Chim. Acta, 358, 3211-3217.  [ISI] [CSD] [CrossRef] [ChemPort]
Kidwai, M., Bhushan, K., Sapra, P., Saxena, R. & Gupta, R. (2000). Bioorg. Med. Chem. 8, 69-72.  [CrossRef] [PubMed] [ChemPort]
Negm, N. A., Elkholy, Y. M., Zahran, M. K. & Tawfik, S. M. (2010). Corros. Sci. 52, 3523-3536.  [CrossRef] [ChemPort]
Nonius (1999). 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]
Souza, M. V. N. (2005). Mini Rev. Med. Chem. 5, 1009-1017.  [PubMed]
Zhenlan, Q., Shenhao, C., Ying, L. & Xuegui, C. (2002). Corros. Sci. 44, 703-715.


Acta Cryst (2013). E69, o581-o582   [ doi:10.1107/S1600536813007307 ]

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