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Volume 69 
Part 9 
Pages o1460-o1461  
September 2013  

Received 10 August 2013
Accepted 15 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.006 Å
R = 0.059
wR = 0.127
Data-to-parameter ratio = 15.5
Details
Open access

3-{[(E)-(2-Hydroxynaphthalen-1-yl)methylidene]amino}pyridinium perchlorate

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000, Algeria,bLaboratory of Solid State Chemistry and Mössbauer Spectroscopy, Laboratories for Inorganic Materials, Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, H3G 1M8, Canada,cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria, and dLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse cedex, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title Schiff base salt, C16H13N2O+·ClO4-, the pyridine ring and the naphthalene ring system are approximately co-planar [making a dihedral angle of 6.05 (12)°] and an intramolecular O-H...N hydrogen bond occurs between the hydroxyl and imino groups. In the crystal, the cations and anions are linked by N-H...O and weak C-H...O hydrogen bonds, forming the supramolecular layers parallel to (100). The crystal studied was an inversion twin refined with minor component = 0.43 (13).

Related literature

For the pharmaceutical and medicinal activity of Schiff bases, see: Dao et al. (2000[Dao, V. T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]); Karthikeyan et al. (2006[Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.]). For the coordination chemistry of Schiff bases, see: Ali et al. (2008[Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.]); Kargar et al. (2009[Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.]); Yeap et al. (2009[Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.]). For the crystal structures of related Schiff base compounds, see: Damous et al. (2011[Damous, M., Hamlaoui, M., Bouacida, S., Merazig, H. & Daran, J.-C. (2011). Acta Cryst. E67, o1123-o1124.]); Fun et al. (2009[Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349-o350.]); Nadeem et al. (2009[Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.]); Eltayeb et al. (2008[Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N2O+·ClO4-

  • Mr = 348.73

  • Orthorhombic, P 21 21 21

  • a = 6.5043 (9) Å

  • b = 14.6915 (19) Å

  • c = 15.398 (3) Å

  • V = 1471.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 180 K

  • 0.25 × 0.04 × 0.03 mm

Data collection
  • Agilent Xcalibur (Sapphire1) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.685, Tmax = 1.000

  • 9582 measured reflections

  • 3369 independent reflections

  • 1695 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.127

  • S = 0.92

  • 3369 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1362 Friedel pairs

  • Absolute structure parameter: 0.43 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.82 2.545 (4) 147
N5-H5...O13i 0.86 2.09 2.844 (5) 146
C2-H2...O11 0.93 2.44 3.354 (5) 166
C3-H3...O1ii 0.93 2.59 3.260 (5) 129
C13-H13...O12iii 0.93 2.57 3.451 (6) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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 & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1012).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5730 ).


Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, Algeria, and the Laboratoire de Chimie de Coordination Toulouse, France. Thanks are due to the Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie (via the PNR project) for financial support.

References

Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718-m719.  [CSD] [CrossRef] [ChemPort] [details]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Damous, M., Hamlaoui, M., Bouacida, S., Merazig, H. & Daran, J.-C. (2011). Acta Cryst. E67, o1123-o1124.  [CSD] [CrossRef] [ChemPort] [details]
Dao, V. T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.  [ISI] [CrossRef] [PubMed] [ChemPort]
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, o576-o577.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fun, H.-K., Kia, R., Vijesh, A. M. & Isloor, A. M. (2009). Acta Cryst. E65, o349-o350.  [CSD] [CrossRef] [ChemPort] [details]
Kargar, H., Jamshidvand, A., Fun, H.-K. & Kia, R. (2009). Acta Cryst. E65, m403-m404.  [CSD] [CrossRef] [ChemPort] [details]
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.  [CrossRef] [PubMed] [ChemPort]
Nadeem, S., Shah, M. R. & VanDerveer, D. (2009). Acta Cryst. E65, o897.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.  [CrossRef] [PubMed] [ChemPort]
Yeap, C. S., Kia, R., Kargar, H. & Fun, H.-K. (2009). Acta Cryst. E65, m570-m571.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1460-o1461   [ doi:10.1107/S1600536813023015 ]

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