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

Horton, P.N.; Akkurt, M.; Mohamed, S.K.; Abdelhamid, A.A.; Marzouk, A.A.

doi:10.1107/S1600536812050635

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.065
wR = 0.175
Data-to-parameter ratio = 15.8
Details

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

Peter N. Horton,^a Mehmet Akkurt,^b ^* Shaaban K. Mohamed,^c,^d Antar A. Abdelhamid ^c,^d and Adel A. Marzouk ^e

^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-HO hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by O-HO hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C-HO 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); Suslick & Reinert (1988); Tisato et al. (1994). For the synthesis and coordination chemistry of azomethines, see, for example: Singh & Adhikari (2012). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₉H₁₇NO₂
M_r = 291.34
Monoclinic, P 2₁ /c
a = 18.9837 (10) Å
b = 4.740 (2) Å
c = 16.105 (8) Å
= 92.927 (9)°
V = 1447.3 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.982, T_max = 0.997
7947 measured reflections
3169 independent reflections
2836 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.175
S = 1.06
3169 reflections
200 parameters
6 restraints
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.88	1.86	2.567 (2)	136
O2-H2O1ⁱ	0.84	2.08	2.710 (2)	132
C11-H11O2ⁱⁱ	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); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

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

organic compounds