4-[(3-Chloro-2-methyl­phen­yl)imino­meth­yl]phenol

Manjunath, B.C.; Abdoh, M.M.M.; Mallesha, L.; Mohana, K.N.; Lokanath, N.K.

doi:10.1107/S1600536812043140

Volume 68
Part 11
Page o3191
November 2012

Received 5 September 2012
Accepted 16 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.123
Data-to-parameter ratio = 13.2
Details

4-[(3-Chloro-2-methylphenyl)iminomethyl]phenol

B. C. Manjunath,^a M. M. M Abdoh,^b L. Mallesha,^c K. N. Mohana ^d and N. K. Lokanath ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,^bDepartment of Physics, Faculty of Science, An Najah National University, Nabtus West Bank, Palestinian Territories,^cPG Department of Studies in Chemistry, JSS College of Arts Commerce and Science, Ooty Road, Mysore 570 025, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C₁₄H₁₂ClNO, the dihedral angle between the aromatic rings is 39.84 (7)°. In th crystal, molecules are connected by O-HN hydrogen bonds into chains parallel to [001]. In addition, a C-H [pi] contact occurs.

Related literature

For the bioactivity of the title compound, see: Corke et al. (1979); Gorrad & Manson (1989). For related structures, see: Jothi et al. (2012); Yaeghoobi et al. (2009).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5271 (9) Å
b = 12.4095 (15) Å
c = 12.5800 (14) Å
V = 1175.1 (2) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 103 K
0.26 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
6050 measured reflections
2042 independent reflections
1856 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.123
S = 1.07
2042 reflections
155 parameters
H-atom parameters constrained
_max = 0.71 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-HA	D-H	HA	DA	D-HA
O2-H2N3ⁱ	0.84	2.05	2.854 (3)	160
C17-H17CCgⁱⁱ	0.98	2.73	3.649 (2)	157
Symmetry codes: (i) $[-x-{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2211 ).

References

Corke, T. C., Bunce, N. J., Beamount, A. L. & Merrick, R. L. (1979). J. Agric. Food Chem. 27, 644-646.
Gorrad, J. W. & Manson, D. (1989). Xenobiotica, 16, 933-955.
Jothi, L., Vasuki, G., Babu, R. R. & Ramamurthi, K. (2012). Acta Cryst. E68, o772.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yaeghoobi, M., Rahman, N. A. & Ng, S. W. (2009). Acta Cryst. E65, o1070.

organic compounds