(E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S160053681000838X

Volume 66
Part 4
Pages o934-o935
April 2010

Received 3 March 2010
Accepted 4 March 2010
Online 27 March 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.052
wR = 0.141
Data-to-parameter ratio = 16.0
Details

(E)-4-Allyl-2-[(2-hydroxyphenyl)iminiomethyl]-6-methoxyphenolate

Naser Eltaher Eltayeb,^a ⁺ Siang Guan Teoh,^a Suchada Chantrapromma ^b ⁺⁺ and Hoong-Kun Fun ^c ^*⁺⁺⁺

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The title compound, C₁₇H₁₇NO₃, crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The methoxy group is almost coplanar [C-O-C-C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intramolecular N-HO hydrogen bond generates an S(6) ring motif. In the crystal, the molecules are linked into zigzag chains along [010] by O-HO hydrogen bonds. In addition, weak C-H [pi] interactions are observed.

Related literature

For background to Schiff bases and their applications, see: Dao et al. (2000); Eltayeb & Ahmed (2005a,b); Karthikeyan et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb et al. (2009); Tan & Liu (2009). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₇H₁₇NO₃
M_r = 283.32
Orthorhombic, P b c a
a = 14.719 (3) Å
b = 9.1302 (16) Å
c = 20.597 (4) Å
V = 2768.0 (9) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.50 × 0.15 × 0.02 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.955, T_max = 0.998
16563 measured reflections
4056 independent reflections
2744 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.141
S = 1.00
4056 reflections
254 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8-C13 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1O1O2ⁱ	0.95	1.72	2.6443 (16)	166
O1-H1O1O3ⁱ	0.95	2.55	3.1268 (16)	119
N1-H1N1O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14-H14BCg1ⁱⁱ	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5052 ).

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.
Eltayeb, N. E. & Ahmed, T. A. (2005a). J. Sci. Tech. 6, 51-59.
Eltayeb, N. E. & Ahmed, T. A. (2005b). Sudan J. Basic Sci. 7, 97-108.
Eltayeb, N. E., Teoh, S. G., Yeap, C. S., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o2065-o2066.
Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.
Tan, G.-X. & Liu, X.-C. (2009). Acta Cryst. E65, o559.

organic compounds