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Volume 69 
Part 1 
Page o106  
January 2013  

Received 12 December 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.065
wR = 0.175
Data-to-parameter ratio = 15.8
Details
Open access

1-{(Z)-[3-(1-Hydroxyethyl)anilino]methylidene}naphthalen-2(1H)-one

aSchool of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ England, England,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 Science, Minia University, El-Minia, Egypt, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C19H17NO2, the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5)°, while the torsion angle of the C-N-C-C bridging group is 179.24 (17)°. The methyl group of the 1-phenylethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The molecular conformation is stabilized by an intramolecular N-H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by O-H...O hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C-H...O interactions, forming a two-dimensional slab-like network parallel to the bc plane.

Related literature

For the biological and industrial properties of Schiff bases, see: Keypour et al. (2009[Keypour, H., Rezaeivala, M., Valencia, L., Perez-Lourido, P. & Khavasi, H. R. (2009). Polyhedron, 28, 3755-3758.]); Suslick & Reinert (1988[Suslick, K. S. & Reinert, T. J. (1988). J. Chem. Educ. 62, 974-983.]); Tisato et al. (1994[Tisato, F., Refosco, F. & Bandoli, G. (1994). Coord. Chem. Rev. 135, 325-397.]). For the synthesis and coordination chemistry of azomethines, see, for example: Singh & Adhikari (2012[Singh, K. B. & Adhikari, D. (2012). Int. J. Basic Appl. Chem. Sci. 2, 84-107.]). 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.]). 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
  • C19H17NO2

  • Mr = 291.34

  • Monoclinic, P 21 /c

  • a = 18.9837 (10) Å

  • b = 4.740 (2) Å

  • c = 16.105 (8) Å

  • [beta] = 92.927 (9)°

  • V = 1447.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.21 × 0.10 × 0.03 mm

Data collection
  • Rigaku AFC12 (Right) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.997

  • 7947 measured reflections

  • 3169 independent reflections

  • 2836 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.175

  • S = 1.06

  • 3169 reflections

  • 200 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.88 1.86 2.567 (2) 136
O2-H2...O1i 0.84 2.08 2.710 (2) 132
C11-H11...O2ii 0.95 2.55 3.327 (3) 140
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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.]), PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) 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: SU2542 ).


Acknowledgements

The EPSRC National Crystallography Service is gratefully acknowledged for the X-ray diffraction data. The authors are thankful to Manchester Metropolitan and Erciyes Universitry for supporting this study.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Keypour, H., Rezaeivala, M., Valencia, L., Perez-Lourido, P. & Khavasi, H. R. (2009). Polyhedron, 28, 3755-3758.  [ISI] [CSD] [CrossRef] [ChemPort]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, K. B. & Adhikari, D. (2012). Int. J. Basic Appl. Chem. Sci. 2, 84-107.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suslick, K. S. & Reinert, T. J. (1988). J. Chem. Educ. 62, 974-983.  [CrossRef]
Tisato, F., Refosco, F. & Bandoli, G. (1994). Coord. Chem. Rev. 135, 325-397.  [CrossRef] [ISI]


Acta Cryst (2013). E69, o106  [ doi:10.1107/S1600536812050635 ]

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