2-[(E)-(2,4-Dimethyl­phen­yl)imino­meth­yl]phenol

Fun, H.-K.; Quah, C.K.; Viveka, S.; Madhukumar, D.J.; Nagaraja, G.K.

doi:10.1107/S1600536811026110

Volume 67
Part 8
Page o1933
August 2011

Received 28 June 2011
Accepted 1 July 2011
Online 6 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.122
Data-to-parameter ratio = 12.9
Details

2-[(E)-(2,4-Dimethylphenyl)iminomethyl]phenol

Hoong-Kun Fun,^a ^*⁺ Ching Kheng Quah,^a ⁺⁺ S. Viveka,^b D. J. Madhukumar ^b and G. K. Nagaraja ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, C₁₅H₁₅NO, contains two independent molecules, both of which exist in trans configurations with respect to the C=N bonds [1.278 (2) and 1.279 (2) Å]. In each molecule, intramolecular O-HN hydrogen bonds generate S(6) ring motifs. In one molecule, the benzene rings form a dihedral angle of 13.38 (9)°, while in the other molecule the dihedral angle is 30.60 (10)°. In the crystal, the two independent molecules are linked via weak intermolecular C-HO hydrogen bonds.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Gallant et al. (2004); Kulkarni (1975); Zhao et al. (1988); Ma & Zhao (1988). For a related structure, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3161 (4) Å
b = 12.0287 (7) Å
c = 28.1634 (15) Å
V = 2478.5 (2) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.51 × 0.35 × 0.32 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.963, T_max = 0.976
39373 measured reflections
4117 independent reflections
3381 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.122
S = 1.02
4117 reflections
319 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1OAN1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B-H1OBN1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A-H5AAO1Bⁱ	0.93	2.56	3.455 (2)	162
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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: LH5275 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

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.
Fun, H.-K., Quah, C. K., Viveka, S., Madhukumar, D. J. & Prasad, D. J. (2011). Acta Cryst. E67, o1932.
Gallant, A. J., Patrick, B. O. & MacLachlan, M. J. (2004). J Org Chem. 69, 8739-8744.
Kulkarni, V. H. (1975). Asian J. Chem. 7, 50-54.
Ma, X. Y. & Zhao, G. (1988). Polyhedron, 7, 1101-1105.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhao, G., Li, F., Xie, J. & Ma, X. Y. (1988). Polyhedron, 7, 393-398.

organic compounds