2-[(2-Meth­oxy­benzyl­idene)amino]­phenol

Aslam, M.; Anis, I.; Afza, N.; Hussain, M.T.; Yousuf, S.

doi:10.1107/S1600536812016224

Volume 68
Part 5
Page o1447
May 2012

Received 23 March 2012
Accepted 14 April 2012
Online 21 April 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.100
Data-to-parameter ratio = 13.7
Details

2-[(2-Methoxybenzylidene)amino]phenol

M. Aslam,^a,^b ⁺ I. Anis,^b N. Afza,^a M. T. Hussain ^c and S. Yousuf ^d ^*

^aPharmaceutical Research Centre, PCSIR Laboratories Complex, Karachi, Pakistan and Department of Chemistry, University of Karachi, Karachi, Pakistan,^bDepartment of Chemistry, University of Karachi, Karachi, Pakistan,^cDepartment of Applied Sciences, National Textile University, Faisalabad 37610, Pakistan, and ^dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title compound, C₁₄H₁₃NO₂, the azomethine double bond adopts an E conformation and the benzene rings form a dihedral angle of 77.70 (7)°. In the crystal, molecules are linked by O-HN and C-HO hydrogen bonds and arranged in a zigzag fashion, forming infinite chains parallel to the c axis, resulting in a graph-set R₂²(9) motif.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009); Gerdemann et al. (2002); Samadhiya & Halve (2001). For a related structure, see: Liang et al. (2009). For graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Monoclinic, P 2₁ /c
a = 9.8709 (5) Å
b = 6.6606 (3) Å
c = 18.6128 (9) Å
= 105.249 (1)°
V = 1180.63 (10) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 273 K
0.49 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.959, T_max = 0.986
6660 measured reflections
2186 independent reflections
1680 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.100
S = 1.04
2186 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AN1ⁱ	0.88 (2)	1.94 (2)	2.796 (2)	163 (2)
C10-H10AO2ⁱ	0.93	2.56	3.269 (2)	133
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2528 ).

Acknowledgements

MA express his gratitude to the Pakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi, the Department of Chemistry, University of Karachi and the H·E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing financial support, research facilities and X-ray diffraction facilities, respectively.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gerdemann, C., Eicken, C. & Krebs, B. (2002). Acc. Chem. Res. 35, 183-191.
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.
Liang, Z.-P., Jian, L., Yang, C.-Y. & Tai, X.-S. (2009). J. Chem. Crystallogr. 39, 708-710.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Samadhiya, S. & Halve, A. (2001). Orient. J. Chem. 17, 119-122.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds