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Volume 69 
Part 6 
Pages o850-o851  
June 2013  

Received 30 April 2013
Accepted 3 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.135
Data-to-parameter ratio = 18.8
Details
Open access

1-{(E)-[(2-Fluoro-5-nitrophenyl)imino]methyl}naphthalen-2-ol

aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,dChemistry Department, Faculty of Sccience, Mini University, 61519 El-Minia, Egypt, and eAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England
Correspondence e-mail: shaabankamel@yahoo.com

The title molecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the molecular conformation is stabilized by an N-H...O hydrogen bond forming an S(6) ring motif. The H atom of the intramolecular hydrogen bond was found to be disordered over two sites and thus both the hydroxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hydroxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hydroxy form. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming layers parallel to (101). [pi]-[pi] stacking interactions [centroid-centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.

Related literature

For the broad range of biological applications of Schiff bases, see, for example: Cozzi (2004[Cozzi, P. G. (2004). Chem. Soc. Rev. 33, 410-421.]); Chandra & Sangeetika (2004[Chandra, S. & Sangeetika, J. (2004). J. Indian Chem. Soc. 81, 203-206.]); Sari et al. (2003[Sari, N., Arslan, S., Logoglu, E. & Sakiyan, I. (2003). Gazi Univ. J. Sci. 16, 283-288.]); Verma et al. (2004[Verma, M., Pandeya, S. N., Singh, K. N. & Stabler, J. P. (2004). Acta Pharm. 54, 49-56.]). For the significance of fluorine atoms in drug structures, see: Blair et al. (2000[Blair, J. B., Kurrasch-Orbaugh, D., Marona-Lewicka, D., Cumbay, M. G., Watts, V. J., Barker, E. L. & Nichols, D. E. (2000). J. Med. Chem. 43, 4701-4710.]); Kirk et al. (1979[Kirk, K. L., Cantacuzene, D., Nimitkitpaisan, Y., McCulloh, D., Padgett, W. L., Daly, J. W. & Creveling, C. R. (1979). J. Med. Chem. 22, 1493-1497.]); LeBars et al. (1987[LeBars, D., Luthra, S. K., Pike, V. W. & LuDuc, C. (1987). Appl. Radiat. Isot. 38, 1073-1077.]). For a related structure, see: Akkurt et al. (2012[Akkurt, M., Kennedy, A. R., Mohamed, S. K., Abdelhamid, A. A. & Miller, G. J. (2012). Acta Cryst. E68, o3168.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11FN2O3

  • Mr = 310.28

  • Monoclinic, P 21 /c

  • a = 14.2226 (6) Å

  • b = 13.0856 (5) Å

  • c = 7.3801 (3) Å

  • [beta] = 94.151 (4)°

  • V = 1369.92 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 123 K

  • 0.5 × 0.2 × 0.05 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.973, Tmax = 0.994

  • 15943 measured reflections

  • 4043 independent reflections

  • 3166 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.135

  • S = 1.07

  • 4043 reflections

  • 215 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.88 (1) 1.68 (2) 2.4969 (16) 152 (4)
C3-H3...O3i 0.95 2.48 3.222 (2) 135
C14-H14...O1ii 0.95 2.35 3.1724 (19) 145
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5319 ).


Acknowledgements

The University of Strathclyde, Erciyes University and Manchester Metropolitan University are gratefully acknowledged for supporting this study.

References

Akkurt, M., Kennedy, A. R., Mohamed, S. K., Abdelhamid, A. A. & Miller, G. J. (2012). Acta Cryst. E68, o3168.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blair, J. B., Kurrasch-Orbaugh, D., Marona-Lewicka, D., Cumbay, M. G., Watts, V. J., Barker, E. L. & Nichols, D. E. (2000). J. Med. Chem. 43, 4701-4710.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chandra, S. & Sangeetika, J. (2004). J. Indian Chem. Soc. 81, 203-206.  [ChemPort]
Cozzi, P. G. (2004). Chem. Soc. Rev. 33, 410-421.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kirk, K. L., Cantacuzene, D., Nimitkitpaisan, Y., McCulloh, D., Padgett, W. L., Daly, J. W. & Creveling, C. R. (1979). J. Med. Chem. 22, 1493-1497.  [CrossRef] [ChemPort] [PubMed] [ISI]
LeBars, D., Luthra, S. K., Pike, V. W. & LuDuc, C. (1987). Appl. Radiat. Isot. 38, 1073-1077.  [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sari, N., Arslan, S., Logoglu, E. & Sakiyan, I. (2003). Gazi Univ. J. Sci. 16, 283-288.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Verma, M., Pandeya, S. N., Singh, K. N. & Stabler, J. P. (2004). Acta Pharm. 54, 49-56.  [PubMed] [ChemPort]


Acta Cryst (2013). E69, o850-o851   [ doi:10.1107/S1600536813012099 ]

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